Verwendung von Aryl- und Hetarylcarboxamiden als Endoparasitizide

Die vorliegende Anmeldung betrifft bekannte und neue Aryl- und Hetarylcarboxamide und ihre Verwendung als Parasitizide gegen Endoparasiten in Tieren oder Menschen, sowie Parasitizide, insbesondere Endoparasitizide, die Aryl- und Hetarylcarboxamide enthalten.

Im Bereich der Tiermedizin stellt das Auftreten von Resistenzen gegen alle kommerziell verfügbaren Anthelmintika ein zunehmendes Problem dar, demzufolge Endoparasitizide mit neuen molekularen Wirkmechanismen benötigt werden. Solche Verbindungen sollten exzellente Effektivität gegen ein breites Helminthen- bzw. Nematodenspektrum zeigen und zugleich bei den behandelten Tieren keine toxischen Effekte hervorrufen. EndoparasitizideMittel sind Arzneimittel, die zur Bekämpfung von Endoparasiten in Menschen und Tieren angewendet werden.

Bestimmte Phenacylbenzamide werden in der WO-A 2001/060783 für die orale Anwendung als Anthelmintika für die Veterinärmedizin beansprucht.

Isothiazolcarboxamide sind aus der WO-A 1999/24413, Heterocyclylethylcarboxamid-Derivate aus der WO-A 2006/108791, Heterocyclylethylbenzamid-Derivate aus der WO-A 2006/108792, N-(l-Methyl-2- phenylethyl)-benzamide aus der WO-A 2007/060162, N-(l -Methyl-2-phenylethyl)-carboxamide aus der WO-A 2007060164, N-Phenethylcarboxamid-Derivative aus der WO-A 2007/060166, N-(3- Phenylpropyl)-carboxamide aus der WO-A 2008/101976, Pyrazolcarboxamide aus der WO-A 2008/148570 und WO-A 2010/063700, Pyrazinylcarboxamide aus der WO-A 2011/128989 sowie verschiedene 2-Pyridylethylcarboxamid-Derivate aus der WO-A 2004/016088, WO-A 2004/074280, WO-A 2005/014545, WO-A 2005/058828, WO-A 2005/058833 und WO-A 2005/085238 als agrochemische Fungizide bekannt. Ferner sind N-2-(Hetero)arylethyl-carboxamid-Derivate in WO-A 2007/108483 als Fungizide und Nematizide beschrieben. Die Verwendung von 2- Pyridylethylcarboxamid-Derivaten wird in der WO-A 2008/126922 explizit zur Anwendung gegen Nematoden im Pflanzenanbau beansprucht.

Die Anwendung dieser vorbekannten (Het)arylethyl- bzw. (Het)arylpropyl-Carboxamide als Endoparasitizide im Bereich der Veterinärmedizin ist bislang nicht beschrieben.

Es wurde nun gefunden, dass Verbindungen der Formel (I),

in welcher

X für ein ein- oder mehrfach durch M substituiertes Phenyl, Thienyl oder Furanyl steht; Q für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl, Pyridyl, Thienyl, Furanyl oder Isothiazolyl steht;

Y für Wasserstoff oder für gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)- Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (Ci-Cio)-Halogenalkyl, (C ₂ -Cio)-Halogenalkenyl, (C ₂ - Cio)-Halogenalkinyl, (Ci-Cio)-Alkoxy, (C ₂ -Cio)- Alkenyloxy, (C3-Cio)-Alkinyloxy, (C3-C14)- Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe steht;

W für Sauerstoff oder Schwefel steht;

L ¹ für -C(R ^U ,R ¹² )-, Sauerstoff, Schwefel, oder ^(R ¹ )- steht;

L ² für -C(R ²¹ ,R ²² )- steht;

L ³ für -C(R ³¹ ,R ³² )- oder Direktbindung steht;

M ¹ für Wasserstoff, Halogen, Cyano, Nitro, OH, (Ci-Cio)-Alkyl, (Ci-Cio)-Halogenalkyl, (C1-C10)- Alkoxy, (Ci-Cio)-Halogenalkoxy, (Ci-Cio)-Alkylthio, (Ci-Cio)-Halogenalkylthio, (C1-C10)- Alkylsulfonyl, (Ci-Cio)-Halogenalkylsulfonyl, (Ci-Cio)-Alkylsulfanyl, (C1-C10)- Halogenalkylsulfanyl, (3- bis 14-gliedrige cyclische Gruppe)-0- steht;

R ¹ für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (Ci-Cio)-Halogenalkyl, (C ₂ -Cio)-Halogenalkenyl, (C2-C10)- Halogenalkinyl, (C3-Cio)-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe steht;

R ¹¹ , R ¹² für jeweils unabhängig voneinander Wasserstoff, Halogen oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (C1-C10)- Halogenalkyl, (C ₂ -Cio)-Halogenalkenyl, (C ₂ -Cio)-Halogenalkinyl, (Ci-Cio)-Alkoxy, (C2-C10)- Alkenyloxy, (C3-Cio)-Alkinyloxy, (C3-Ci4)-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe steht;

R ^u , R ¹² zusammen für eine jeweils gegebenenfalls ein- oder mehrfach durch M ² substituierte spiro- verknüpfte 3- bis 14-gliedrige carbo- oder 3- bis 10-gliedrige heterocyclische Gruppe stehen;

R ²¹ , R ²² für jeweils unabhängig voneinander Wasserstoff, Halogen oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (C1-C10)- Halogenalkyl, (C ₂ -Cio)-Halogenalkenyl, (C ₂ -Cio)-Halogenalkinyl, (Ci-Cio)-Alkoxy, (C1-C10)- Halogenalkoxy, (C ₂ -Cio)-Alkenyloxy, (C3-Cio)-Alkinyloxy, (C3-Ci4)-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe steht;

R ²¹ , R ²² zusammen für eine jeweils gegebenenfalls ein- oder mehrfach durch M ² substituierte spiro- verknüpfte 3- bis 14-gliedrige carbo- oder 3- bis 10-gliedrige heterocyclische Gruppe stehen;

R ³¹ , R ³² für jeweils unabhängig voneinander Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (Ci-Cio)-Halogenalkyl, (C ₂ - Cio)-Halogenalkenyl, (C2-Cio)-Halogenalkinyl, (C3-Ci4)-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe steht;

R ³¹ , R ³² zusammen für eine jeweils gegebenenfalls ein- oder mehrfach durch M ² substituierte spiro- verknüpfte 3- bis 14-gliedrige carbo- oder 3- bis 10-gliedrige heterocyclische Gruppe stehen;

M ² für jeweils unabhängig voneinander für Halogen, Formyl, Cyano, Nitro, (Ci-Cio)-Alkyl, (Ci-Cio)- Halogenalkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Halogenalkenyl, (C ₂ -Cio)-Alkinyl, (C2-C10)- Halogenalkinyl, (Ci-Cio)-Alkoxy, (Ci-Cio)-Halogenalkoxy, (C ₂ -Cio)-Alkenyloxy, (C2-C10)- Halogenalkenoxy, (C3-Cio)-Alkinyloxy, (C3-Cio)-Halogenalkinoxy, (Ci-Cio)-Alkylthio, (C1-C10)- Halogenalkylthio, (C ₂ -Cio)-Alkenylthio, (C ₂ -Cio)-Halogenalkenylthio, (C3-Cio)-Alkinylthio, (C3- Cio)-Halogenalkinylthio, (Ci-Cio)-Alkylsulfonyl, (Ci-Cio)-Halogenalkylsulfonyl, (C2-C10)- Alkenylsulfonyl, (C ₂ -Cio)-Halogenalkenylsulfonyl, (C3-Cio)-Alkinylsulfonyl, (C3-C10)- Halogenalkinylsulfonyl, (Ci-Cio)-Alkylsulfanyl, (Ci-Cio)-Halogenalkylsulfanyl, (C2-C10)- Alkenylsulfanyl, (C ₂ -Cio)-Halogenalkenylsulfanyl, (C3-Cio)-Alkinylsulfanyl, (C3-C10)- Halogenalkinylsulfanyl, (Ci-Cio)-Alkylcarbonyl, (Ci-Cio)-Halogenalkylcarbonyl, (C2-Cio)-Alkenyl- carbonyl, (C2-Cio)-Halogenalkenylcarbonyl, (C2-Cio)-Alkinylcarbonyl, (C2-C10)-

Halogenalkinylcarbonyl, (Ci-Cio)-Alkoxycarbonyl, (Ci-Cio)-Halogenalkoxycarbonyl, (C2-C10)- Alkenoxycarbonyl, (C2-Cio)-Halogenalkenoxycarbonyl, (C3-Cio)-Alkinoxycarbonyl, (C3-C10)- Halogenalkinoxycarbonyl, (Ci-Cio)-Alkylcarbonyloxy, (Ci-Cio)-Halogenalkylcarbonyloxy, (C2-C10)- Alkenylcarbonyloxy, (C2-Cio)-Halogenalkenylcarbonyloxy, (C2-Cio)-Alkinylcarbonyloxy, (C2-C10)- Halogenalkinylcarbonyloxy, 3 bis 14-gliedrige cyclische Gruppe steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I); als Arzneimittel in Tieren oder Menschen, insbesondere gegen Endoparasiten, verwendet werden.

Die Verbindungen der Formel (I) können gegebenenfalls in Abhängigkeit von der Art der Substituenten als geometrische und/oder als optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen. Die Erfindung betrifft sowohl die reinen Isomere als auch die Isomerengemische. Die erfindungsgemäßen Verbindungen können auch als Metallkomplexe vorliegen. Definitionen

Der Begriff Tiere umfasst nicht den Menschen.

Der Begriff„ein- oder mehrfach" bedeutet bevorzugt ein- bis sechsfach, besonders bevorzugt ein- bis vierfach, ganz besonders bevorzugt ein- bis dreifach und insbesonders ganz bevorzugt ein- oder zweifach.

Der Fachmann ist sich bewusst, dass die Ausdrücke "ein",„eine" oder„eines" wie in dieser Anmeldung genutzt je nach Situation "ein/eine/eines (1)", "ein/eine/eines (1) oder mehr" oder "mindestens ein/eine/eines (1)" bedeuten kann.

Für alle bisher beschriebenen Ringsysteme gilt, dass benachbarte Atome nicht -O-O- oder -O-S- sein dürfen.

Strukturen mit einer variablen Anzahl an möglichen Kohlenstoffatomen (C-Atomen) werden zur Vereinfachung in der vorliegenden Anmeldung als Ci-Cio-Strukturen bezeichnet (Ci-Cio). Beispiel: eine Alkylgruppe aus 1 bis 10 C-Atomen entspricht (Ci-Cio)-Alkyl. Ringstrukturen aus C-Atomen und Heteroatomen werden als„3 bis 14-gliedrige" Strukturen bezeichnet.

Steht ein Sammelbegriff für einen Substituenten, z. B. (Ci-Cio)-Alkyl, am Ende eines zusammengesetzten Substituenten wie z.B. (C3-Ci ₄ )-Cycloalkyl-(Ci-Cio)-alkyl, so kann der am Ende stehende Bestandteil des zusammengesetzten Substituenten, z.B. das (Ci-Cio)-Alkyl, ein- bzw. mehrfach, gleich oder verschieden und unabhängig voneinander mit dem am Anfang stehenden Substituenten, z. B. (C3-Ci ₄ )-Cycloalkyl, substituiert sein.

Die Definition für Sammelbegriffe solange nicht anders definiert gilt auch für diese Sammelbegriffe in zusammengesetzten Substituenten. Beispiel: Die Definition für (Ci-Cio)-Alkyl gilt auch für (Ci-Cio)- Alkyl als Bestandteil eines zusammengesetzten Substituenten wie z.B. (C3-Ci4)-Cycloalkyl-(Ci-Cio)- alkyl.

Dem Fachmann ist klar, dass in dieser Anmeldung genannte Beispiele nicht als beschränkend anzusehen sind sondern lediglich einige Ausführungsformen näher beschreiben.

Bei den in den vorstehenden Formeln angegebenen Definitionen der Symbole wurden Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Substituenten stehen: Sammelbegriffe

Halogen, soweit nicht anders definiert: Elemente der 7. Hauptgruppe, bevorzugt ist Fluor, Chlor, Brom bzw. Iod.

(Ci-Cio)-Alkyl, soweit nicht an anderer Stelle anders definiert: gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste bevorzugt mit (CI-CÖ)-, besonders bevorzugt (C1-C4)- Kohlenstoffatomen. Beispiele: Methyl, Ethyl, iso-Propyl, n-Propyl, 1 -Methylethyl, Butyl, tert. Butyl, etc.

(C ₂ -Cio)-Alkenyl, soweit nicht an anderer Stelle anders definiert: ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit einer Doppelbindung. Bevorzugt ist (C2-C6)- bzw. (C2-C4)- Alkenyl. Beispiele: Ethenyl, 1 -Propenyl, 3-Butenyl, etc.

(C ₂ -Cio)-Alkinyl, soweit nicht an anderer Stelle anders definiert: ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit einer Dreifachbindung. Bevorzugt ist (C2-C6)- bzw. (C2-C4)- Alkinyl. Beispiele: Ethinyl, 1-Propinyl, etc.

(Ci-Cio)-Alkoxy (Alkylrest-O-), soweit nicht an anderer Stelle anders definiert: ein Alkylrest, der über ein Sauerstoffatom (-0-) an das Gerüst gebunden ist. Bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkoxy. Beispiele: Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, etc.

Analog sind (C2-Cio)-Alkenoxy und (C3-Cio)-Alkinoxy, soweit nicht an anderer Stelle anders definiert Alkenylreste bzw. Alkinylreste, die über -O- an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C4)-Alkenoxy. Bevorzugt (C3-C6)- bzw. (C3-C4)-Alkinoxy.

(Ci-Cio)-Alkylcarbonyl (Alkylrest-C(=0)-), soweit nicht an anderer Stelle anders definiert: bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonylgruppe.

Analog sind (C2-Cio)-Alkenylcarbonyl und (C2-Cio)-Alkinylcarbonyl, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über -C(=0)- an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C4)-Alkenylcarbonyl. Bevorzugt ist (C2-C6)- bzw. (C2-C4)- Alkinylcarbonyl.

(Ci-Cio)-Alkoxycarbonyl (Alkylrest-0-C(=0)-), soweit nicht an anderer Stelle anders definiert: bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe.

Analog sind (C2-Cio)-Alkenoxycarbonyl und (C3-Cio)-Alkinoxycarbonyl, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C4)-Alkenoxycarbonyl. Bevorzugt ist (C3-C6)- bzw. (C3-C4)- Alkinoxycarbonyl.

(Ci-Cio)-Alkylcarbonyloxy (Alkylrest-C(=0)-0-), soweit nicht an anderer Stelle anders definiert: ein Alkylrest, der über eine Carbonyloxygruppe (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden ist. Bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkylcarbonyloxy

Analog sind (C2-Cio)-Alkenylcarbonyloxy und (C2-Cio)-Alkinylcarbonyloxy, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über (-C(=0)-0-) an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C i)-Alkenylcarbonyloxy Bevorzugt ist (C2-C6)- bzw. (C2-C4)- Alkinylcarbonyloxy.

(Ci-Cio)-Alkylthio, soweit nicht an anderer Stelle anders definiert: Alkylrest, der über -S- an das Gerüst gebunden ist. Bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkylthio.

Analog sind (C2-Cio)-Alkenylthio und (C3-Cio)-Alkinylthio, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über -S- an das Gerüst gebunden sind. Bevorzugt ist (C2- CÖ)- bzw. (C2-C4)-Alkenylthio. Bevorzugt ist (C3-C6)- bzw. (C3-C4)-Alkinylthio.

(Ci-Cio)-Alkylsulfinyl, soweit nicht an anderer Stelle anders definiert: Alkylrest, der über -S(=0)- an das Gerüst gebunden ist. Bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkylsulfinyl.

Analog sind (C ₂ -Cio)-Alkenylsulfinyl und (C3-Cio)-Alkinylsulfinyl, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über -S(=0)- an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C4)-Alkenylsulfinyl. Bevorzugt ist (C3-C6)- bzw. (C3-C4)- Alkinylsulfinyl.

(Ci-Cio)-Alkylsulfonyl, soweit nicht an anderer Stelle anders definiert: Alkylrest, der über -S(=0) ₂ - an das Gerüst gebunden ist. Bevorzugt ist (CI-CÖ)- bzw. (Ci-C4)-Alkylsulfonyl.

Analog sind (C ₂ -Cio)-Alkenylsulfonyl und (C3-Cio)-Alkinylsulfonyl, soweit nicht an anderer Stelle anders definiert: Alkenylreste bzw. Alkinylreste, die über -S(=0)2- an das Gerüst gebunden sind. Bevorzugt ist (C2-C6)- bzw. (C2-C4)-Alkenylsulfonyl. Bevorzugt ist (C3-C6)- bzw. (C3-C4)- Alkinylsulfonyl.

(Ci-Cio)-Halogenalkyl, (C2-Cio)-Halogenalkenyl, (C2-Cio)-Halogenalkinyl, (Ci-Cio)-Halogenalkoxy, (C2-Cio)-Halogenalkenoxy, (C3-Cio)-Halogenalkinoxy, (Ci-Cio)-Halogenalkylcarbonyl, (C2-C10)- Halogenalkenylcarbonyl, (C ₂ -Cio)-Halogenalkinylcarbonyl, (Ci-Cio)-Halogenalkoxycarbonyl, (C ₂ -C ₁ 0)- Halogenalkenoxycarbonyl, (C3-Cio)-Halogenalkinoxycarbonyl, (C2-Cio)-Halogenalkylcarbonyloxy, (C2- Cio)-Halogenalkenylcarbonyloxy, (C2-Cio)-Halogenalkinylcarbonyloxy, (Ci-Cio)-Halogenalkylthio, (C2- Cio)-Halogenalkenylthio, (C3-Cio)-Halogenalkinylthio, (Ci-Cio)-Halogenalkylsulfinyl, (C2-C10)- Halogenalkenylsulfinyl, (C3-Cio)-Halogenalkinylsulfinyl, (Ci-Cio)-Halogenalkylsulfonyl, (C2-C10)- Halogenalkenylsulfonyl, (C3-Cio)-Halogenalkinylsulfonyl sind jeweils soweit nicht anders definiert analog zu (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (Ci-Cio)-Alkoxy, (C ₂ -Cio)-Alkenoxy, (C ₃ - Cio)-Alkinoxy, (Ci-Cio)-Alkylcarbonyl, (C2-Cio)-Alkenylcarbonyl, (C2-Cio)-Alkinylcarbonyl, (C1-C10)- Alkoxycarbonyl, (C2-Cio)-Alkenoxycarbonyl, (C3-Cio)-Alkinoxycarbonyl, (Ci-Cio)-Alkylcarbonyloxy, (C2-Cio)-Alkenylcarbonyloxyl, (C2-Cio)-Alkinylcarbonyloxy, (Ci-Cio)-Alkylthio, (C2-Cio)-Alkenylthio, (C ₃ -Cio)-Alkinylthio, (Ci-Cio)-Alkylsulfmyl, (C ₂ -Cio)-Alkenylsulfmyl, (C ₃ -Cio)-Alkinylsulfmyl, (Ci- Cio)-Alkylsulfonyl, (C3-Cio)-Alkenylsulfonyl, (C3-Cio)-Alkinylsulfonyl definiert, wobei mindestens ein Wasserstoffatom durch ein Halogenatom wie vorstehend genannt ersetzt ist. In einer Ausführungsform sind alle Wasserstoffatome durch Halogen ersetzt. Beispiele für halogenierte Strukturen sind z. B. Chlormethyl, Trichlormethyl, Fluormethyl, Chlordifluormethyl, Dichlorfluormethyl, Trifluormethyl, 2,2- Difluorethyl, Difluormethyl, Difluormethoxy, Trifluormethoxy, Difluormethylthio, Trifluormethylthio.

Cyclische Gruppen

3 bis 14-gliedrige cyclische Gruppe, soweit nicht an anderer Stelle anders definiert: (C3-C14)- carbocyclische Gruppe, 3 bis 10-gliedrige heterocyclische Gruppe, halogenierte (C3-Ci4)-carbocyclische Gruppe, halogenierte 3 bis 10-gliedrige heterocyclische Gruppe.

(C3-Ci ₄ )-carbocyclische Gruppe, soweit nicht an anderer Stelle anders definiert: (C3-Ci ₄ )-Cycloalkyl, (C3-Ci4)-Cycloalkenyl, (C6-Ci4)-Aryl, halogeniertes (C3-Ci4)-Cycloalkyl, halogeniertes (C3-C14)- Cycloalkenyl, halogeniertes (C6-Ci ₄ )-Aryl.

(C3-Ci ₄ )-Cycloalkyl, soweit nicht an anderer Stelle anders definiert: mono-, bi- oder tricyclische, gesättigte Kohlenwasserstoffgruppen, bevorzugt mit (C3-C14)-, (C3-C8)- bzw. (C3-C6)- ingatomen. Ein Cycloalkyl kann auch eine spirocyclische Gruppe sein. Beispiele: Cyclopropyl, -butyl, -pentyl, -hexyl, - heptyl, Bicyclo[2.2.1]heptyl oder Adamantyl. Bevorzugt steht„Cycloalkyl" für monocyclische Gruppen aus 3, 4, 5, 6 oder 7 Ringatomen.

Analog ist (C3-Ci ₄ )-Cycloalkenyl, soweit nicht an anderer Stelle anders definiert: eine mono-, bi- oder tricyclische jedoch partiell ungesättigte Kohlenwasserstoffgruppe mit mindestens einer Doppelbindung, bevorzugt mit (C3-C8)- bzw. (C3-C6)-Ringatomen. Beispiele: Cyclopropenyl, Cyclobutenyl, Cyclopentenyl und Cyclohexenyl.

(C6-Ci ₄ )-Aryl, soweit nicht an anderer Stelle anders definiert: mono- bi- oder tricyclische Ringsystemgruppe wobei mindestens ein Cyclus aromatisch ist, bevorzugt mit (CÖ-CS)- bzw. (CÖ)- Ringatomen. Bevorzugt ist Aryl eine aromatische C6-monocyclische Ringsystemgruppe; eine bicyclische (C8-Ci4)-Ringsystemgruppe; oder eine tricyclische (Cio-Ci4)-Ringsystemgruppe. Beispiele: Phenyl, Naphthyl, Anthryl, Phenanthryl, Tetrahydronaphthyl, Indenyl, Indanyl, Fluorenyl.

Halogenierte (C3-Ci4)-carbocyclische Gruppe, halogeniertes (C3-Ci4)-Cycloalkyl, halogeniertes (C3- Ci4)-Cycloalkenyl, halogeniertes (C6-Ci4)-Aryl sind jeweils soweit nicht anders definiert analog zu (C3- Ci ₄ )-carbocyclische Gruppe, (C3-Ci ₄ )-Cycloalkyl, (C3-Ci ₄ )-Cycloalkenyl, (C6-Ci ₄ )-Aryl definiert, wobei mindestens ein Wasserstoffatom durch ein Halogenatom wie vorstehend genannt ersetzt ist. In einer Ausführungsform sind alle Wasserstoffatome durch Halogen ersetzt. Beispiele für halogenierte Strukturen sind 3-Chlorphenyl, 2-Bromcyclopentyl.

Heteroatom: zum Beispiel N, O, S, P, B, Si.

3 bis 10-gliedrige heterocyclische Gruppe, soweit nicht an anderer Stelle anders definiert: 3 bis 9- gliedrige Heterocyclylgruppe oder 5 bis 10-gliedrige Heteroarylgruppe, halogenierte 3 bis 9-gliedrige Heterocyclylgruppe oder halogenierte 5 bis 10-gliedrige Heteroarylgruppe.

3 bis 9-gliedriges Heterocyclyl, soweit nicht an anderer Stelle anders definiert: 3 bis 9-gliedrige gesättigte oder partiell ungesättigte mono-, bi- oder tricyclische Ringsystemgruppe, aus C-Atomen und mindestens einem Heteroatom, vorzugsweise ausgewählt aus N, O und/oder S. Bevorzugt ist das Ringsystem ein 3 bis 6-gliedriges Ringsystem. Bevorzugt enthält das Ringsystem 1 , 2, 3 oder 4 Heteroatome, besonders bevorzugt 1 oder 2 Heteroatome. Ebenfalls bevorzugt ist ein monocyclisches Ringsystem. In einer weiteren bevorzugten Ausführungsform ist ein monocyclisches Ringsystem ein partiell ungesättigtes monocyclisches Ringsystem mit einer Doppelbindung. Ein Heterocyclyl kann ein spirocyclisches System sein. Beispiele: Piperazinyl, Dihydropyridyl, Morpholinyl, etc.. Diese Definition gilt auch für Heterocyclyl als Bestandteil eines zusammengesetzten Substituenten wie z.B. 3 bis 9- gliedriges Heterocyclyl(Ci-Cio)-alkyl, sofern an anderer Stelle nicht definiert.

5 bis 10-gliedriges Heteroaryl, soweit nicht an anderer Stelle anders definiert: mono- bi- oder tricyclische 5 bis 10-gliedrige heterocyclische Gruppe aus C-Atomen und mindestens einem Heteroatom, wobei mindestens ein Cyclus aromatisch ist, vorzugsweise ausgewählt aus N, O und/oder S. Bevorzugt ist das Ringsystem ein ein 5 bis 6-gliedriges Ringsystem. In einer Ausführungsform ist Heteroaryl ein aromatisches monocyclisches Ringsystem aus 5 oder 6 Ringatomen. Bevorzugt ist Heteroaryl als ein aromatisches monocyclisches Ringsystem, enthaltend 1 bis 4 Heteroatome aus der Gruppe O, N, oder S. Weiterhin kann Heteroaryl ein bicyclisches Ringsystem darstellen, das aus 8 bis 14 Ringatomen besteht oder ein tricyclisches Ringsystem, das aus 13 bis 14 Ringatomen besteht. Beispiele: Furyl, Thienyl, Pyrazolyl, Imidazolyl, Triazolyl, Thiazolyl, Indolyl, Benzimidazolyl, Indazolyl, Benzofuranyl, Benzothiophenyl, Benzothiazolyl, Benzoxazolyl, Chinolinyl, Isochinolinyl. Diese Definition gilt auch für Heteroaryl als Bestandteil eines zusammengesetzten Substituenten wie z.B. 5 bis 10-gliedriges Heteroaryl(C5-Cio)-alkyl, sofern an anderer Stelle nicht definiert. Im folgenden sind 5- und 6-gliedrige Heteroarylgruppen näher beschrieben:

5- gliedriges Heteroaryl, soweit nicht an anderer Stelle anders definiert: Heteroarylgruppe enthaltend ein bis drei bzw. ein bis vier N-, O- und/oder S-Atom(e) als Ringatome. Beispiele: Furanyl, Thienyl, Oxazolyl, Thiazolyl. In einer Ausführungsform enthält eine 5-gliedrige Heteroarylgruppe neben C- Atomen ein bis vier N-Atome bzw. ein bis drei N-Atome als Ringglieder. Beispiele: Pyrrolyl, Pyrazolyl, Triazolyl, Imidazolyl. In einer weiteren Ausführungsform enthält ein 5-gliedriges Heteroaryl ein bis drei N-Atome oder ein N-Atom und ein O- oder S-Atom. Beispiele: Thiazolyl, Oxazolyl, Oxadiazolyl.

6- gliedriges Heteroaryl, soweit nicht an anderer Stelle anders definiert: Heteroarylgruppe enthaltend ein bis drei bzw. ein bis vier N-Atom(e) als Ringatome. In einer Ausführungsform enthält eine 6- gliedrige Heteroarylgruppe ein bis drei N-Atome. Beispiele: Pyridyl, Pyridazinyl, Pyrimidinyl, Pyrazinyl, Triazinyl, Tetrazinyl.

Halogenierte 3 bis 9-gliedrige Heterocyclylgruppe oder halogenierte 5 bis 10-gliedrige Heteroarylgruppe jeweils soweit nicht anders definiert sind analog wie 3 bis 9-gliedrige Heterocyclylgruppe oder 5 bis 10- gliedrige Heteroarylgruppe definiert, wobei mindestens ein Wasserstoffatom durch ein Halogenatom wie vorstehend genannt ersetzt ist. In einer Ausführungsform sind alle Wasserstoffatome durch Halogen ersetzt. Beispiel für halogenierte heterocyclische Strukturen: 3-Chlortetrahydrothiopyran-2-yl, 4- Chlorpyridin-2-yl.

Nicht umfasst sind solche Kombinationen, die den Naturgesetzen widersprechen und die der Fachmann daher aufgrund seines Fachwissens ausgeschlossen hätte. Beispielsweise sind Ringstrukturen mit drei oder mehreren benachbarten O-Atomen ausgeschlossen.

Ausführungsformen der erfindungsgemäßen Verbindungen

Dem Fachmann ist offenbar, dass alle Ausführungsformen alleine oder in Kombination vorliegen können.

Die Verbindungen der Formel (I) können gegebenenfalls in Abhängigkeit der Art der Substituenten als Salze, Tautomere, geometrische und/oder optisch aktive Isomere oder entsprechende Isomerengemische in unterschiedlicher Zusammensetzung vorliegen.

Die erfindungsgemäßen Verbindungen können gegebenenfalls in verschiedenen polymorphen Formen oder als Mischung verschiedener polymorpher Formen vorliegen. Sowohl die reinen Polymorphe als auch die Polymorphgemische sind Gegenstand der Erfindung und können erfindungsgemäß verwendet werden. Im Folgenden werden Ausführungsformen der Verbindungen der Formel (I) näher beschrieben:

X steht besonders bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl, 2-Thienyl, 3- Thienyl, 2-Furanyl oder 3-Furanyl;

X steht besonders bevorzugt für ein ein- bis dreifach durch M ¹ substituiertes Phenyl oder 2-Thienyl, 3-Thienyl, 2-Furanyl, 3-Furanyl;

X steht besonders bevorzugt für ein einfach durch M ¹ substituiertes Phenyl;

X steht besonders bevorzugt für ein einfach durch M ¹ substituiertes Thienyl;

X steht besonders bevorzugt für ein einfach durch M ¹ substituiertes Furanyl;

X steht besonders bevorzugt für ein zweifach durch M ¹ substituiertes Phenyl;

X steht besonders bevorzugt für ein zweifach durch M ¹ substituiertes Thienyl;

X steht besonders bevorzugt für ein zweifach durch M ¹ substituiertes Furanyl;

Q steht für ein ein- oder mehrfach durch M ¹ substituiertes Pyridyl, Thienyl, Furanyl oder Isothiazolyl;

Q steht bevorzugt für folgende Strukturelemente, wobei n für jedes Q jeweils wie unten angegeben definiert ist:

Q Q ² Q ³ Q ⁴

n = 1-3 n = 1-3 n = 1-3 n = 1-3

Q ⁵ Q ⁶ Q ⁷ Q ⁸

n = 1-2 n = 1-5 n = 1-4 n = 1-4

Q steht bevorzugt für folgende Strukturelemente, wobei n für jedes Q jeweils wie unten angegeben definiert ist:

Q ⁵ Q ⁷ Q ⁸

n = 1-2 n = 1-4 n = 1-4

Q steht besonders bevorzugt für ein- oder mehrfach durch M ¹ substituiertes 2-Thienyl, 3- Thienyl, 2- Furanyl, 5-Isothiazolyl, Phenyl, 3-Pyridyl oder 2-Pyridyl;

Q steht besonders bevorzugt für ein- oder zweifach durch M ¹ substituiertes 2-Thienyl, 3- Thienyl, 2- Furanyl, 5-Isothiazolyl, Phenyl, 3-Pyridyl oder 2-Pyridyl;

Q steht ganz besonders bevorzugt für 2-Thienyl, 3-Fluor-2-thienyl, 3-Chlor-2-thienyl, 3,4-Dichlor-2- thienyl, 3,4,5-Trichlor-2-thienyl, 3-Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl- 2-thienyl, 3-(Trifluormethyl)-2-thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 3-Thienyl, 2- Fluor-3 -thienyl, 2-Chlor-3 -thienyl, 2-Brom-3 -thienyl, 2-Iod-3 -thienyl, 2-Cyano-3 -thienyl, 2- Methyl-3 -thienyl, 2-(Trifluormethyl)-3 -thienyl, 2-Methoxy-3 -thienyl, 2-Ethoxy-3 -thienyl, 2- Furanyl, 3-Fluor-2-furanyl, 3-Chlor-2-furanyl, 3-Brom-2-furanyl, 3-Iod-2-furanyl, 3-Cyano-2- furanyl, 3-Methyl-2-furanyl, 3-(Trifluormethyl)-2-furanyl, 3-Methoxy-2-furanyl, 3-Ethoxy-2- furanyl, 3-Furanyl, 2-Chlor-3-furanyl, 2-Brom-3-furanyl, 2-Iod-3-furanyl, 2-Cyano-3-furanyl, 2- Methyl-3-furanyl, 2-(Trifluormethyl)-3-furanyl, 2-Methoxy-3-furanyl, 2-Ethoxy-3-furanyl, 4- Chlor-5-isothiazolyl, 3,4-Dichlor-5-isothiazolyl, 2-Fluor-phenyl, 2,6-Difluor-phenyl, 2-Chor- phenyl, 2,6-Dichlor-phenyl, 2-Brom-phenyl, 2-Iod-phenyl, 2-(Difluormethyl)-phenyl, 2- (Trifluormethyl)-phenyl, 2-Chlor-3-pyridyl, 3-Chlor-2-pyridyl oder 2-(Trifluormethyl)-3-pyridyl;

Q steht insbesonders ganz besonders bevorzugt für 3-Chlor-2-thienyl, 3,4,5-Trichlor-2-thienyl, 3- Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl-2-thienyl, 3-(Trifluormethyl)-2- thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 2-Chlor-3 -thienyl, 2-Brom-3 -thienyl, 2-Iod-3- thienyl, 2-Methyl-3 -thienyl, 3-Brom-2-furanyl, 3-Methyl-2-furanyl, 2-Chlor-3-furanyl, 2-Brom-3- furanyl, 2-Iod-3-furanyl, 2-Methyl-3-furanyl, 3,4-Dichlor-5-isothiazolyl, 2-Fluor-phenyl, 2,6- Difluor-phenyl, 2-Chor-phenyl, 2,6-Dichlor-phenyl, 2-Brom-phenyl, 2-Iod-phenyl, 2- (Difluormethyl)-phenyl, 2-(Trifluormethyl)-phenyl, 2-Chlor-3-pyridyl, 3-Chlor-2-pyridyl oder 2- (Trifluormethyl)-3 -pyridyl;

Q steht besonders bevorzugt für ein- oder mehrfach durch M ¹ substituiertes 2-Thienyl, 3- Thienyl, 2- Furanyl, 5-Isothiazolyl, 3-Pyridyl oder 2-Pyridyl;

Q steht besonders bevorzugt für ein- oder zweifach durch M ¹ substituiertes 2-Thienyl, 3- Thienyl, 2- Furanyl, 5-Isothiazolyl, 3-Pyridyl oder 2-Pyridyl;

Q steht ganz besonders bevorzugt für 2-Thienyl, 3-Fluor-2-thienyl, 3-Chlor-2-thienyl, 3,4-Dichlor-2- thienyl, 3,4,5-Trichlor-2-thienyl, 3-Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl- 2-thienyl, 3-(Trifluormethyl)-2-thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 3-Thienyl, 2- Fluor-3 -thienyl, 2-Chlor-3 -thienyl, 2-Brom-3 -thienyl, 2-Iod-3 -thienyl, 2-Cyano-3 -thienyl, 2- Methyl-3 -thienyl, 2-(Trifluormethyl)-3 -thienyl, 2-Methoxy-3 -thienyl, 2-Ethoxy-3 -thienyl, 2- Furanyl, 3-Fluor-2-furanyl, 3-Chlor-2-furanyl, 3-Brom-2-furanyl, 3-Iod-2-furanyl, 3-Cyano-2- furanyl, 3-Methyl-2-furanyl, 3-(Trifluormethyl)-2-furanyl, 3-Methoxy-2-furanyl, 3-Ethoxy-2- furanyl, 3-Furanyl, 2-Chlor-3 -furanyl, 2-Brom-3-furanyl, 2-Iod-3 -furanyl, 2-Cyano-3 -furanyl, 2- Methyl-3 -furanyl, 2-(Trifluormethyl)-3 -furanyl, 2-Methoxy-3 -furanyl, 2-Ethoxy-3-furanyl, 4- Chlor-5-isothiazolyl, 3,4-Dichlor-5-isothiazolyl, 2-Chlor-3 -pyridyl, 3-Chlor-2-pyridyl oder 2- (Trifluormethyl)-3 -pyridyl;

Q steht insbesonders ganz besonders bevorzugt für 3-Chlor-2-thienyl, 3,4,5-Trichlor-2-thienyl, 3- Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl-2-thienyl, 3-(Trifluormethyl)-2- thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 2-Chlor-3 -thienyl, 2-Brom-3 -thienyl, 2-Iod-3- thienyl, 2-Methyl-3 -thienyl, 3-Brom-2-furanyl, 3-Methyl-2-furanyl, 2-Chlor-3 -furanyl, 2-Brom-3- furanyl, 2-Iod-3 -furanyl, 2-Methyl-3-furanyl, 3,4-Dichlor-5-isothiazolyl, 2-Chlor-3 -pyridyl, 3- Chlor-2-pyridyl oder 2-(Trifluormethyl)-3 -pyridyl;

Y steht bevorzugt für Wasserstoff oder für gegebenenfalls ein- oder mehrfach durch M substituiertes (Ci-Cio)-Alkyl, (C ₂ -Cio)-Alkenyl, (C ₂ -Cio)-Alkinyl, (Ci-Cio)-Halogenalkyl, (C ₂ - Cio)-Halogenalkenyl, (C2-Cio)-Halogenalkinyl, (Ci-Cio)-Alkoxy, (C2-Cio)-Alkenyloxy, (C3-C10)- Alkinyloxy, (C3-Ci4)-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte 3- bis 14-gliedrige cyclische Gruppe;

Y steht bevorzugt für Wasserstoff oder für gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₂ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C2-C4)- Halogenalkenyl, (C3-C4)-Halogenalkinyl, (Ci-C4)-Alkoxy, (C2-C4)-Alkenyloxy, (C3-C4)- Alkinyloxy, (C3-C6)-Cycloalkyl-(Ci-C ₄ )-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte C3- bis Cö-gliedrige carbocyclische Gruppe;

Y steht besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec- Butyl, iso-Butyl, tert.-Butyl, Cyanomethyl, 2,2-Difluor-ethyl, 2,2,2-Trifluor-ethyl, Allyl, Butenyl, Propargyl, Butinyl, 3,3-Dichlor-prop-2-enyl, Methoxy, Ethoxy, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl;

Y steht ganz besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec- Butyl, iso-Butyl, tert.-Butyl, Methoxy, Ethoxy, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl;

Y steht ganz besonders bevorzugt für Wasserstoff, Cyclopropyl; W steht bevorzugt für Sauerstoff;

W steht bevorzugt für Schwefel;

L ¹ steht bevorzugt für -C(R ^U ,R ¹² )-, Sauerstoff oder -N^ ¹ )-;

L ¹ steht ganz besonders bevorzugt für -C(R ^U ,R ¹² )- oder -N^R ¹ )-;

L ¹ steht ganz besonders bevorzugt für -C(R ^U ,R ¹² )-;

L ¹ steht ganz besonders bevorzugt für Sauerstoff;

L ¹ steht ganz besonders bevorzugt für -N^R ¹ )-;

L ³ steht bevorzugt für eine Direktbindung;

L ³ steht bevorzugt für -C(R ³¹ ,R ³² )-;

M ¹ steht bevorzugt für Wasserstoff, Halogen, Cyano, Nitro, OH, (Ci-C6)-Alkyl, (Ci-Ce)- Halogenalkyl, (Ci-C ₆ )-Alkoxy, (Ci-C ₆ )-Halogenalkoxy, (Ci-C ₆ )-Alkylthio, (Ci-C ₆ )- Halogenalkylthio, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Halogenalkylsulfonyl, (Ci-C6)-Alkylsulfanyl, (Ci-C ₆ )-Halogenalkylsulfanyl, (C ₃ -Ci ₄ )-Cycloalkyl-0-, (C ₃ -Ci ₄ )-Cycloalkenyl-0-, (C ₆ -Ci ₄ )-Aryl- O-, halogeniertes (C3-Ci4)-Cycloalkyl-0-, halogeniertes (C3-Ci4)-Cycloalkenyl-0-, halogeniertes

M ¹ steht bevorzugt für Wasserstoff, Halogen, Cyano, Nitro, OH, (Ci-C ₄ )-Alkyl, (C1-C4)- Halogenalkyl, (Ci-C ₄ )-Alkoxy, (Ci-C ₄ )-Halogenalkoxy, (Ci-C ₄ )-Alkylthio, (C1-C4)- Halogenalkylthio, (Ci-C ₄ )-Alkylsulfonyl, (Ci-C ₄ )-Halogenalkylsulfonyl, (Ci-C ₄ )-Alkylsulfanyl, (Ci-C ₆ )-Halogenalkylsulfanyl, (C ₃ -Ci ₄ )-Cycloalkyl-0-, (C ₃ -Ci ₄ )-Cycloalkenyl-0-, (C ₆ -Ci ₄ )-Aryl- O-, halogeniertes (C3-Ci4)-Cycloalkyl-0-, halogeniertes (C3-Ci4)-Cycloalkenyl-0-, halogeniertes

M ¹ steht ganz besonders bevorzugt für Wasserstoff, Halogen, Cyano, Nitro, OH, (Ci-C4)-Alkyl, (Ci- C ₄ )-Halogenalkyl, (Ci-C ₄ )-Alkoxy, (Ci-C ₄ )-Halogenalkoxy, (Ci-C ₄ )-Alkylthio, (Ci-C ₄ )- Halogenalkylthio, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Halogenalkylsulfonyl, (Ci-C4)-Alkylsulfanyl, (Ci-C6)-Halogenalkylsulfanyl, (C6-Ci4)-Aryl-0-, halogeniertes (C6-Ci4)-Aryl)-0-;

M ¹ steht ganz besonders bevorzugt für Wasserstoff, Fluor, Brom, Chlor, Iod, Cyano, Nitro, OH, Methyl, Ethyl, iso-Propyl, tert.-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, iso- Propoxy, Trifluormethoxy, Difluormethoxy, Methylthio, Trifluormethylthio, Difluormethylthio, 2,2,2-Trifluorethylthio, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, 2,2,2- Trifluorethylsulfonyl, Methylsulfanyl, Ethylsulfanyl, Trifluormethylsulfanyl, 2,2,2-

Trifluorethylsulfanyl oder Phenoxy;

M ¹ steht insbesonders ganz besonders bevorzugt für Wasserstoff, Fluor, Brom, Chlor, Iod, Cyano, Methyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, iso-Propoxy oder Phenoxy;

R ¹ steht bevorzugt für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₆ )-Alkyl, (C ₂ -C ₆ )-Alkenyl, (C ₂ -C ₆ )-Alkinyl, (Ci-C ₆ )-Halogenalkyl, (C ₂ -C ₆ )-Halogenalkenyl, (C ₂ -C6)-Halogenalkinyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte (C3-C14)- carbocyclische Gruppe;

R ¹ steht besonders bevorzugt für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C2-C4)- Halogenalkenyl, (C ₂ -C ₄ )-Halogenalkinyl, (C3-C ₄ )-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte (C3-C8)-Cycloalkyl oder halogeniertes (C ₃ -C ₈ )-Cycloalkyl;

R ¹ steht besonders bevorzugt für Wasserstoff oder Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Cyclopropylmethyl oder Cyclopropyl;

R ¹ steht ganz besonders bevorzugt für Wasserstoff oder (Ci-C ₄ )-Alkyl;

R ¹ steht besonders bevorzugt für Wasserstoff oder Methyl, Ethyl, n-Propyl, iso-Propyl;

R ¹¹ , R ¹² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-Cio)-Alkyl, (Ci-Cio)-Halogenalkyl, (Ci-Cio)-Alkoxy, (C3-Ci ₄ )-Cycloalkyl-(Ci-Cio)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M substituierte (C3-C14)- carbocyclische Gruppe;

R ¹¹ , R ¹² steht besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C6)-Alkyl, (Ci-C6)-Halogenalkyl, (Ci-C ₆ )-Alkoxy, (C3-C ₆ )-Cycloalkyl-(Ci-C ₆ )-alkyl, (C ₃ -C ₈ )-Cycloalkyl oder halogeniertes (C ₃ -C ₈ )- Cycloalkyl;

R ¹¹ , R ¹² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder (Ci-C ₆ )-Alkyl, (Ci-C ₆ )-Halogenalkyl, (Ci-C ₆ )-Alkoxy, (C3-C ₆ )-Cycloalkyl-(Ci-C ₆ )-alkyl, (C ₃ -C ₆ )- Cycloalkyl;

R ¹¹ , R ¹² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Trifluormethyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl;

R ¹¹ , R ¹² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl;

R ¹¹ , R ¹² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl;R ^u , R ¹² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Methoxy, Ethoxy oder

R ¹¹ , R ¹² steht ganz besonders bevorzugt für C(R ^U , R ¹² ) als spiro-C(CH ₂ -CH ₂ );

R ¹¹ , R ¹² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, (Ci-C ₆ )-Alkoxy oder (Ci-C ₆ )-Alkyl;

R ¹¹ , R ¹² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Halogen, (Ci-C ₆ )-Halogenalkyl, (Ci-C ₆ )-Alkoxy oder (Ci-C ₆ )-Alkyl;R ^u , R ¹² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Methoxy, Methyl, Ethyl;

R ¹¹ , R ¹² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Methoxy, Methyl, Ethyl, Trifluormethyl, Fluor;

R ²¹ , R ²² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₆ )-Alkyl, (C ₂ -C ₆ )-Alkenyl, (C2-C ₆ )-Alkinyl, (Ci-C ₆ )- Halogenalkyl, (C ₂ -C6)-Halogenalkenyl, (C ₂ -C6)-Halogenalkinyl, (Ci-C6)-Alkoxy, (Ci-Ce)- Halogenalkoxy, (C2-C6)-Alkenyloxy, (C3-C6)-Alkinyloxy, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte (C3-C14)- carbocyclische Gruppe;

R ²¹ , R ²² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Alkmyl, (C1-C4)- Halogenalkyl, (C2-C4)-Halogenalkenyl, (C2-C4)-Halogenalkinyl, (Ci-C6)-Alkoxy, (C1-C4)- Halogenalkoxy, (C2-C4)-Alkenyloxy, (C3-C4)-Alkinyloxy, (C3-C4)-Cycloalkyl-(Ci-C4)-alkyl, (C3- Cg)-Cycloalkyl oder halogeniertes (C3-Cg)-Cycloalkyl;

R ²¹ , R ²² steht besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C4)-Alkyl, (C2-C4)-Alkenyl, (C2- C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (Ci-C ₆ )-Alkoxy, (C ₂ -C ₄ )-Alkenyloxy, (C ₃ -C ₄ )-Alkinyloxy, (C3-C ₄ )-Cycloalkyl-(Ci-C ₄ )-alkyl, (C ₃ -C ₆ )-Cycloalkyl;

R ²¹ , R ²² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor, Methyl, Ethyl, n- Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl ;

R ²¹ , R ²² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder (Ci-C ₄ )-Alkyl, (Ci-C ₄ )-Halogenalkyl;

R ²¹ , R ²² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Fluor oder Methyl, Ethyl;

R ²¹ , R ²² steht ganz besonders bevorzugt für C(R ²¹ , R ²² ) als spiro-C(CH ₂ -CH ₂ );

R ³¹ , R ³² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₆ )-Alkyl, (C ₂ -C ₆ )-Alkenyl, (C2-C ₆ )-Alkinyl, (Ci-C ₆ )- Halogenalkyl, (C2-C6)-Halogenalkenyl, (C2-C6)-Halogenalkinyl, (Ci-C6)-Alkoxy, (CI-CÖ)- Halogenalkoxy, (C2-C6)-Alkenyloxy, (C3-C6)-Alkinyloxy, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte (C3-C14)- carbocyclische Gruppe;

R ³¹ , R ³² steht bevorzugt für jeweils unabhängig voneinander Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Alkinyl, (C1-C4)- Halogenalkyl, (C2-C4)-Halogenalkenyl, (C2-C4)-Halogenalkinyl, (Ci-C6)-Alkoxy, (C1-C4)- Halogenalkoxy, (C2-C4)-Alkenyloxy, (C3-C4)-Alkinyloxy, (C3-C4)-Cycloalkyl-(Ci-C4)-alkyl oder für eine gegebenenfalls ein- oder mehrfach durch M ² substituierte (C3-C8)-Cycloalkyl oder halogeniertes (C3-Cg)-Cycloalkyl; R steht besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C i)-Alkyl, (Ci-C i)-Halogenalkyl, (C2-C4)- Halogenalkenyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Alkinyl, (Ci-C ₆ )-Alkoxy, (C ₂ -C ₄ )-Alkenyloxy, (C3-C4)- Alkinyloxy, (C3-C ₄ )-Cycloalkyl-(Ci-C ₄ )-alkyl, (C ₃ -C ₆ )-Cycloalkyl;

R ³² steht besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Methyl, Ethyl, n- Propyl, iso-Propyl, tert-Butyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl;

R ³² steht ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff oder (C1-C4)- Alkyl;

R ³² steht insbesonders ganz besonders bevorzugt für jeweils unabhängig voneinander Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl oder tert-Butyl;

R ³² steht ganz besonders bevorzugt für C(R ³¹ , R ³² ) als spiro-C(CH ₂ -CH ₂ ); steht bevorzugt jeweils unabhängig voneinander für Halogen, Formyl, Cyano, Nitro, (Ci-Ce)- Alkyl, (Ci-C ₆ )-Halogenalkyl, (C ₂ -C ₆ )-Alkenyl, (C ₂ -C ₆ )-Halogenalkenyl, (C ₂ -C ₆ )-Alkinyl, (C ₂ -C ₆ )- Halogenalkinyl, (Ci-C6)-Alkoxy, (Ci-C6)-Halogenalkoxy, (CuG-CoG)-Alkenyloxy, (C ₂ -Ce)- Halogenalkenoxy, (C3-C6)-Alkinyloxy, (C3-C6)-Halogenalkinoxy, (Ci-C6)-Alkylthio, (Ci-Ce)- Halogenalkylthio, (C ₂ -C ₆ )-Alkenylthio, (C ₂ -C ₆ )-Halogenalkenylthio, (C3-C ₆ )-Alkinylthio, (C ₃ -C ₆ )- Halogenalkinylthio, (Ci-C6)-Alkylsulfonyl, (Ci-C6)-Halogenalkylsulfonyl, (C ₂ -Ce)- Alkenylsulfonyl, (C ₂ -C6)-Halogenalkenylsulfonyl, (C3-C6)-Alkinylsulfonyl, (C3-C6)- Halogenalkinylsulfonyl, (Ci-C6)-Alkylsulfanyl, (Ci-C6)-Halogenalkylsulfanyl, (C ₂ -Ce)- Alkenylsulfanyl, (C ₂ -C6)-Halogenalkenylsulfanyl, (C3-C6)-Alkinylsulfanyl, (C3-C6)- Halogenalkinylsulfanyl, Formyl, (Ci-C6)-Alkylcarbonyl, (Ci-C6)-Halogenalkylcarbonyl, (C ₂ -Ce)-Al- kenylcarbonyl, (C ₂ -C6)-Halogenalkenylcarbonyl, (C ₂ -C6)-Alkinylcarbonyl, (C ₂ -Ce)- Halogenalkinylcarbonyl, (Ci-C6)-Alkoxycarbonyl, (Ci-C6)-Halogenalkoxycarbonyl, (C ₂ -Ce)- Alkenoxycarbonyl, (C ₂ -C6)-Halogenalkenoxycarbonyl, (C3-C6)-Alkinoxycarbonyl, (C3-Ce)-Halogen- alkinoxycarbonyl, (Ci-C6)-Alkylcarbonyloxy, (Ci-C6)-Halogenalkylcarbonyloxy, (C ₂ -Ce)- Alkenylcarbonyloxy, (C ₂ -C6)-Halogenalkenylcarbonyloxy, (C ₂ -C6)-Alkinylcarbonyloxy, (C ₂ -Ce)- Halogenalkinylcarbonyloxy oder (C3-Ci ₄ )-Cycloalkyl. steht besonders bevorzugt jeweils unabhängig voneinander für Halogen, Formyl, Cyano, Nitro, (Ci-C ₄ )-Alkyl, (Ci-C ₄ )-Halogenalkyl, (C ₂ -C ₄ )-Alkenyl, (C ₂ -C ₄ )-Halogenalkenyl, (C ₂ -C ₄ )-Alkinyl, (C ₂ -C ₄ )-Halogenalkinyl, (Ci-C ₄ )-Alkoxy, (Ci-C ₄ )-Halogenalkoxy, (C ₂ -C ₄ )-Alkenyloxy, (C2-C4)- Halogenalkenoxy, (C3-C ₄ )-Alkinyloxy, (C3-C ₄ )-Halogenalkinoxy, (Ci-C ₄ )-Alkylthio, (C1-C4)- Halogenalkylthio, (C ₂ -C ₄ )-Alkenylthio, (C ₂ -C ₄ )-Halogenalkenylthio, (C ₃ -C ₄ )-Alkmylthio, (C3-C4)- Halogenalkinylthio, (Ci-C4)-Alkylsulfonyl, (Ci-C4)-Halogenalkylsulfonyl, (C2-C4)- Alkenylsulfonyl, (C ₂ -C4)-Halogenalkenylsulfonyl, (C3-C4)-Alkinylsulfonyl, (C3-C ₄ )- Halogenalkinylsulfonyl, (Ci-C4)-Alkylsulfanyl, (Ci-C4)-Halogenalkylsulfanyl, (C ₂ -C ₄ )- Alkenylsulfanyl, (C ₂ -C4)-Halogenalkenylsulfanyl, (C3-C4)-Alkinylsulfanyl, (C3-C ₄ )- Halogenalkinylsulfanyl, (Ci-C4)-Alkylcarbonyl, (Ci-C4)-Halogenalkylcarbonyl, (C ₂ -C4)-Alkenylcar- bonyl, (C ₂ -C4)-Halogenalkenylcarbonyl, (C ₂ -C4)-Alkinylcarbonyl, (C ₂ -C4)-Halogenalkinylcarbonyl, (Ci-C4)-Alkoxycarbonyl, (Ci-C4)-Halogenalkoxycarbonyl, (C ₂ -C4)-Alkenoxycarbonyl, (C ₂ -C ₄ )- Halogenalkenoxycarbonyl, (C3-C4)-Alkinoxycarbonyl, (C3-C4)-Halogenalkinoxycarbonyl, (C ₁ -C ₄ )- Alkylcarbonyloxy, (Ci-C4)-Halogenalkylcarbonyloxy, (C2-C4)-Alkenylcarbonyloxy, (C2-C4)-Halo- genalkenylcarbonyloxy, (C2-C4)-Alkinylcarbonyloxy, (C2-C4)-Halogenalkinylcarbonyloxy oder (C3- C ₆ )-Cycloalkyl.

M ² steht ganz besonders bevorzugt jeweils unabhängig voneinander für Chlor, Fluor, Formyl, Cyano, Nitro, (Ci-C ₄ )-Alkyl, (Ci-C ₄ )-Halogenalkyl, (Ci-C ₄ )-Alkoxy, (Ci-C ₄ )-Halogenalkoxy, (C1-C4)- Alkylthio, (Ci-C ₄ )-Halogenalkylthio, (Ci-C ₄ )-Alkylsulfonyl, (Ci-C ₄ )-Halogenalkylsulfonyl, (Ci- C ₄ )-Alkylsulfanyl, (Ci-C ₄ )-Halogenalkylsulfanyl, (Ci-C ₄ )-Alkylcarbonyl, (C1-C4)- Halogenalkylcarbonyl oder (C3-C6)-Cycloalkyl.

M ² steht ganz besonders bevorzugt jeweils unabhängig voneinander für Fluor, Brom, Chlor, Iod, Cyano, Nitro, Methyl, Ethyl, iso-Propyl, tert.-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, iso-Propoxy, Trifluormethoxy, Difluormethoxy, Methylthio, Trifluormethylthio, Difluormethylthio, 2,2,2-Trifluorethylthio, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, Methylsulfanyl, Ethylsulfanyl, Trifluormethylsulfanyl, 2,2,2- Trifluorethylsulfanyl, Cyclopropyl, Cyclobutyl oder Cyclopentyl.

[053] Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen bzw. Erläuterungen können jedoch auch untereinander, also zwischen den jeweiligen Bereichen und Vorzugsbereichen beliebig kombiniert werden. Sie gelten für die Endprodukte sowie für die Vor- und Zwischenprodukte entsprechend.

[054] Die genannten Definitionen können untereinander in beliebiger Weise kombiniert werden.

Außerdem können auch einzelne Definitionen entfallen.

[055] Bevorzugt, besonders bevorzugt oder ganz besonders bevorzugt sind Verbindungen der

Formel (I), welche jeweils die unter bevorzugt, besonders bevorzugt, ganz besonders bevorzugt oder insbesonders ganz besonders bevorzugt genannten Substituenten tragen.

[056] In einer Ausführungsform sind Verbindungen der Formel (I) Verbindungen W

X ^{/L L} N ^Q

¹ (i)

in welcher L ¹ , L ² , L ³ , Q, W und Y wie oben definiert sind und

X für Phenyl steht, bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, Nitro, OH, (Ci-C ₄ )-Alkyl, (Ci-C ₃ )-Halogenalkyl, (Ci-C ₄ )-Alkoxy, (C1-C3)- Halogenalkoxy, (Ci-C ₄ )-Alkylthio, (Ci-C ₃ )-Halogenalkylthio, (Ci-C ₄ )-Alkylsulfonyl, (C1-C3)- Halogenalkylsulfonyl, (Ci-C ₄ )-Alkylsulfanyl, (Ci-C3)-Halogenalkylsulfanyl oder Phenoxy;

X für Phenyl steht, besonders bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Brom, Chlor, Iod, Cyano, Nitro, OH, Methyl, Ethyl, iso-Propyl, tert.-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, iso-Propoxy, Trifluormethoxy, Difluormethoxy, Methylthio, Trifluormethylthio, Difluormethylthio, 2,2,2-Trifluorethylthio, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, Methylsulfanyl, Ethylsulfanyl, Trifluormethylsulfanyl, 2,2,2-Trifluorethylsulfanyl oder Phenoxy;

X für 2-Thienyl steht, bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, Nitro, OH, gegebenenfalls substituiertes (Ci-C ₄ )-Alkyl, (C1-C3)- Halogenalkyl, (Ci-C ₄ )-Alkoxy oder (Ci-C3)-Halogenalkoxy;

X für 2-Thienyl steht, besonders bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl;

X für 3-Thienyl steht, bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, Nitro, OH, gegebenenfalls substituiertes (Ci-C ₄ )-Alkyl, (C1-C3)- Halogenalkyl, (Ci-C ₄ )-Alkoxy oder (Ci-C3)-Halogenalkoxy;

X für 3-Thienyl steht, besonders bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl;

X für 2-Furanyl steht, bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, Nitro, OH, gegebenenfalls substituiertes (Ci-C ₄ )-Alkyl, (C1-C3)- Halogenalkyl, (Ci-C ₄ )-Alkoxy oder (Ci-C3)-Halogenalkoxy;

X für 2-Furanyl steht, besonders bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl. X für 3-Furanyl steht, bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, Nitro, OH, gegebenenfalls substituiertes (Ci-C4)-Alkyl, (C1-C3)- Halogenalkyl, (Ci-C4)-Alkoxy oder (Ci-C3)-Halogenalkoxy;

X für 3-Furanyl steht, besonders bevorzugt ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl;

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher L ¹ , L ² , L ³ , W, X und Y wie oben definiert sind und

Q bevorzugt für folgende Strukturelemente steht, die ein- oder mehrfach durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, gegebenenfalls substituiertes (Ci-C4)-Alkyl, (Ci-C3)-Halogenalkyl oder (Ci-C ₄ )-Alkoxy substituiert sein können:

Q ¹ Q ² Q ³ Q ⁴

n = 1-3 n = 1-3 n = 1-3 n = 1-3

Q ⁵ Q ⁶ Q ⁷ Q ⁸

n = 1-2 n = 1-5 n = 1-4 n = 1-4 besonders bevorzugt für 2-Thienyl, 3-Fluor-2-thienyl, 3-Chlor-2-thienyl, 3,4-Dichlor-2-thienyl, 3,4,5-Trichlor-2-thienyl, 3-Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl-2- thienyl, 3-(Trifluormethyl)-2-thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 3-Thienyl, 2- Fluor-3-thienyl, 2-Chlor-3-thienyl, 2-Brom-3-thienyl, 2-Iod-3-thienyl, 2-Cyano-3-thienyl, 2- Methyl-3-thienyl, 2-(Trifluormethyl)-3-thienyl, 2-Methoxy-3-thienyl, 2-Ethoxy-3-thienyl, 2- Furanyl, 3-Fluor-2-furanyl, 3-Chlor-2-furanyl, 3-Brom-2-furanyl, 3-Iod-2-furanyl, 3-Cyano-2- furanyl, 3-Methyl-2-furanyl, 3-(Trifluormethyl)-2-furanyl, 3-Methoxy-2-furanyl, 3-Ethoxy-2- furanyl, 3-Furanyl, 2-Chlor-3-furanyl, 2-Brom-3-furanyl, 2-Iod-3-furanyl, 2-Cyano-3-furanyl, 2- Methyl-3-furanyl, 2-(Trifluormethyl)-3-furanyl, 2-Methoxy-3-furanyl, 2-Ethoxy-3-furanyl, 4- Chlor-5-isothiazolyl, 3,4-Dichlor-5-isothiazolyl, 2-Fluor-phenyl, 2,6-Difluor-phenyl, 2-Chor- phenyl, 2,6-Dichlor-phenyl, 2-Brom-phenyl, 2-Iod-phenyl, 2-(Difluormethyl)-phenyl, 2- (Trifluormethyl)-phenyl, 2-Chlor-3-pyridyl, 3-Chlor-2-pyridyl oder 2-(Trifluormethyl)-3-pyridyl steht; bevorzugt für folgende Strukturelemente steht, die ein- oder mehrfach durch M ¹ ausgewählt aus Wasserstoff, Halogen, Cyano, gegebenenfalls substituiertes (Ci-C4)-Alkyl, (Ci-C3)-Halogenalkyl oder (Ci-C i)-Alkoxy substituiert sein können:

Q ¹ Q ² Q ³ Q ⁴ n = 1 -3 n = 1 -3 n = 1 -3 n = 1 -3

Q ⁵ Q ⁷ Q ⁸

n = 1 -2 n = 1 -4 n = 1 -4

Q besonders bevorzugt für 2-Thienyl, 3-Fluor-2-thienyl, 3-Chlor-2-thienyl, 3,4-Dichlor-2-thienyl, 3,4,5-Trichlor-2-thienyl, 3-Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl-2- thienyl, 3-(Trifluormethyl)-2-thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 3-Thienyl, 2- Fluor-3-thienyl, 2-Chlor-3-thienyl, 2-Brom-3-thienyl, 2-Iod-3-thienyl, 2-Cyano-3-thienyl, 2- Methyl-3-thienyl, 2-(Trifluormethyl)-3-thienyl, 2-Methoxy-3-thienyl, 2-Ethoxy-3-thienyl, 2- Furanyl, 3-Fluor-2-furanyl, 3-Chlor-2-furanyl, 3-Brom-2-furanyl, 3-Iod-2-furanyl, 3-Cyano-2- furanyl, 3-Methyl-2-furanyl, 3-(Trifluormethyl)-2-furanyl, 3-Methoxy-2-furanyl, 3-Ethoxy-2- furanyl, 3-Furanyl, 2-Chlor-3-furanyl, 2-Brom-3-furanyl, 2-Iod-3-furanyl, 2-Cyano-3-furanyl, 2- Methyl-3-furanyl, 2-(Trifluormethyl)-3-furanyl, 2-Methoxy-3-furanyl, 2-Ethoxy-3-furanyl, 4- Chlor-5-isothiazolyl, 3,4-Dichlor-5-isothiazolyl, 2-Chlor-3-pyridyl, 3-Chlor-2-pyridyl oder 2- (Trifluormethyl)-3-pyridyl steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I). In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

W

X ^{/L L} N ^Q

¹ (i)

in welcher L ¹ , L ² , L ³ , Q, W und X wie oben definiert sind und

Y bevorzugt für Wasserstoff oder für gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci- C ₄ )-Alkyl, (C ₂ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C ₂ -C ₄ )-Halogenalkenyl, (C ₃ - C ₄ )-Halogenalkinyl, (Ci-C ₄ )-Alkoxy, (C2-C ₄ )-Alkenyloxy, (C3-C ₄ )-Alkinyloxy, (C3-Ce)- Cycloalkyl-(Ci-C ₄ )-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht;

Y besonders bevorzugt für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, iso- Butyl, tert.-Butyl, Cyanomethyl, 2,2-Difluor-ethyl, 2,2,2-Trifluor-ethyl, Allyl, Butenyl, Propargyl, Butinyl, 3,3-Dichlor-prop-2-enyl, Methoxy, Ethoxy, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

W

X ^{/L L} N ^Q

¹ (i)

in welcher L ¹ , L ² , L ³ , Q, X und Y wie oben definiert sind und

W bevorzugt für Sauerstoff steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

W

X ^{/L L} N ^Q

¹ (i)

in welcher L ² , L ³ , Q, W, X und Y wie oben definiert sind und

L ¹ bevorzugt für C(R ^U , R ¹² ) steht, wobei R ¹¹ und R ¹² jeweils unabhängig voneinander für Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₃ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C ₃ -C ₄ )-Halogenalkenyl, (C3-C4)- Halogenalkinyl, (Ci-C ₄ )-Alkoxy, (C3-C ₄ )-Alkenyloxy, (C3-C ₄ )-Alkinyloxy, (C3-C6)-Cycloalkyl- (Ci-C ₄ )-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht, oder wobei R ¹¹ und R ¹² zusammen für eine gegebenenfalls substituierte spiro- verknüpfte 3 bis 6-gliedrige cyclische Gruppe stehen;

L ¹ bevorzugt für Sauerstoff oder Schwefel steht;

L ¹ bevorzugt für -IM^R ¹ ) steht, wobei R ¹ für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₃ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C3-C ₄ )-Halogenalkenyl, (C3-C ₄ )-Halogenalkinyl, (C3-C6)-Cycloalkyl-(Ci-C ₄ )-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht;

L ¹ besonders bevorzugt für C(R ^U , R ¹² ) steht, wobei R ¹¹ und R ¹² jeweils unabhängig voneinander für Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl oder wobei C(R ^U , R ¹² ) für spiro- C(CH ₂ -CH ₂ ) steht;

L ¹ besonders bevorzugt für Sauerstoff steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher L , L , W, X und Y wie oben definiert sind und

Q bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl, Pyridyl, Thienyl, Furanyl oder Isothiazolyl steht;

Q bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Pyridyl, Thienyl, Furanyl oder Isothiazolyl steht;

Q besonders bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl steht; L ¹ bevorzugt für Sauerstoff oder Schwefel steht;

L ¹ bevorzugt für -N^R ¹ ) steht, wobei R ¹ für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C ₃ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C3-C4)-Halogenalkenyl, (C3-C4)-Halogenalkinyl, (C3-C6)-Cycloalkyl-(Ci-C4)-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht;

L ¹ besonders bevorzugt für Schwefel steh^L ¹ besonders bevorzugt für -IM^R ¹ ) steht, wobei R ¹ für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Cyclopropylmethyl oder Cyclopropyl steht;

L ¹ bevorzugt für -C(R ^U ,R ¹² )- steht, wobei R ¹¹ , R ¹² jeweils unabhängig voneinander für Halogen, (Ci- Ce)-Halogenalkyl oder (Ci-Ce)-Alkoxy steht;

L ¹ besonders bevorzugt für -C(R ^U ,R ¹² )- steht, wobei R ^U ,R ¹² unabhängig voneinander für Fluor, Trifluormethyl, Methoxy steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher L ¹ , L ³ , Q, W, X und Y wie oben definiert sind und

L ² bevorzugt für C(R ²¹ , R ²² ) steht, wobei R ²¹ und R ²² jeweils unabhängig voneinander für Wasserstoff, Fluor oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C4)-Alkyl, (C ₃ -C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C ₃ -C ₄ )-Halogenalkenyl, (C3-C4)- Halogenalkinyl, (Ci-C4)-Alkoxy, (C3-C4)-Alkenyloxy, (C3-C4)-Alkinyloxy, (C3-C6)-Cycloalkyl- (Ci-C4)-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht, oder wobei R ²¹ und R ²² zusammen für eine gegebenenfalls substituierte spiro- verknüpfte 3 bis 6-gliedrige cyclische Gruppe stehen;

L ² besonders bevorzugt für C(R ²¹ , R ²² ) steht, wobei R ²¹ und R ²² jeweils unabhängig voneinander für Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl oder wobei C(R ²¹ , R ²² ) für spiro- C(CH ₂ -CH ₂ ) steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher L ¹ , L ² , Q, W, X und Y wie oben definiert sind und

L ³ bevorzugt für C(R ³¹ , R ³² ) steht, wobei R ³¹ und R ³² jeweils unabhängig voneinander für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C4)-Alkyl, (C3- C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C ₃ -C ₄ )-Halogenalkenyl, (C3-C4)- Halogenalkinyl, (Ci-C ₄ )-Alkoxy, (C3-C ₄ )-Alkenyloxy, (C3-C ₄ )-Alkinyloxy, (C3-C6)-Cycloalkyl- (Ci-C ₄ )-alkyl oder für eine gegebenenfalls substituierte C3- bis Cö-gliedrige carbocyclische Gruppe steht, oder wobei R ³¹ und R ³² zusammen für eine gegebenenfalls substituierte spiro- verknüpfte 3 bis 6-gliedrige cyclische Gruppe stehen;

L ³ besonders bevorzugt für C(R ³¹ , R ³² ) steht, wobei R ³¹ und R ³² jeweils unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl oder wobei C(R ³¹ , R ³² ) für spiro- CFh-CFh) steht;

L ³ bevorzugt und besonders bevorzugt für eine Direktbindung zwischen L ² und N-Y steht; sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I). In einer weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher L ¹ , L ² , W, X und Y wie oben definiert sind und

Q bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl, Pyridyl, Thienyl, Furanyl oder Isothiazolyl steht;

Q besonders bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl steht;

Q ganz besonders bevorzugt für ein ein- oder mehrfach durch M ¹ substituiertes Phenyl steht, wobei das Phenyl nicht mit Trifluormethyl in 2-Position substituiert sein kann;

L ³ bevorzugt für C(R ³¹ , R ³² ) steht, wobei R ³¹ und R ³² jeweils unabhängig voneinander für Wasserstoff oder gegebenenfalls ein- oder mehrfach durch M ² substituiertes (Ci-C ₄ )-Alkyl, (C3- C ₄ )-Alkenyl, (C ₃ -C ₄ )-Alkinyl, (Ci-C ₄ )-Halogenalkyl, (C ₃ -C ₄ )-Halogenalkenyl, (C3-C4)- Halogenalkinyl, (Ci-C ₄ )-Alkoxy, (C3-C ₄ )-Alkenyloxy, (C3-C ₄ )-Alkinyloxy, (C3-C6)-Cycloalkyl- (Ci-C ₄ )-alkyl oder für eine gegebenenfalls substituierte C3- bis C6-gliedrige carbocyclische Grappe steht, oder wobei R ³¹ und R ³² zusammen für eine gegebenenfalls substituierte spiro- verknüpfte 3 bis 6-gliedrige cyclische Gruppe stehen;

L ³ besonders bevorzugt für C(R ³¹ , R ³² ) steht, wobei R ³¹ und R ³² jeweils unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl steht;

L ³ besonders bevorzugt für C(R ³¹ , R ³² ) steht, wobei R ³¹ und R ³² jeweils unabhängig voneinander für, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl steht;

sowie Salze, N-Oxide und tautomere Formen der Verbindungen der Formel (I).

In einer ganz besonders bevorzugten weiteren Ausführungsform sind Verbindungen der Formel (I) Verbindungen

in welcher

für ein- oder mehrfach durch M ¹ substituiertes Phenyl steht, wobei M ¹ ausgewählt ist aus Wasserstoff, Fluor, Brom, Chlor, Iod, Cyano, Nitro, OH, Methyl, Ethyl, iso-Propyl, tert.-Butyl, Trifluormethyl, Difluormethyl, Methoxy, Ethoxy, iso-Propoxy, Trifluormethoxy, Difluormethoxy, Methylthio, Trifluormethylthio, Difluormethylthio, 2,2,2-Trifluorethylthio, Methylsulfonyl, Ethylsulfonyl, Trifluormethylsulfonyl, 2,2,2-Trifluorethylsulfonyl, Methylsulfanyl, Ethylsulfanyl, Trifluormethylsulfanyl, 2,2,2-Trifluorethylsulfanyl oder Phenoxy ; für 2-Thienyl steht, ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl; für 3-Thienyl steht, ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl;

X für 2-Furanyl steht, ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl; X für 3-Furanyl steht, ein- oder mehrfach substituiert durch M ¹ ausgewählt aus Wasserstoff, Fluor, Chlor, Brom, Iod, Methyl oder Trifluormethyl;

Q für 2-Thienyl, 3-Fluor-2-thienyl, 3-Chlor-2-thienyl, 3,4-Dichlor-2-thienyl, 3,4,5-Trichlor-2- thienyl, 3-Brom-2-thienyl, 3-Iod-2-thienyl, 3-Cyano-2-thienyl, 3-Methyl-2-thienyl, 3- (Trifluormethyl)-2-thienyl, 3-Methoxy-2-thienyl, 3-Ethoxy-2-thienyl, 3-Thienyl, 2-Fluor-3- thienyl, 2-Chlor-3-thienyl, 2-Brom-3-thienyl, 2-Iod-3-thienyl, 2-Cyano-3-thienyl, 2-Methyl-3- thienyl, 2-(Trifluormethyl)-3-thienyl, 2-Methoxy-3-thienyl, 2-Ethoxy-3-thienyl, 2-Furanyl, 3- Fluor-2-furanyl, 3-Chlor-2-furanyl, 3-Brom-2-furanyl, 3-Iod-2-furanyl, 3-Cyano-2-furanyl, 3- Methyl-2-furanyl, 3-(Trifluormethyl)-2-furanyl, 3-Methoxy-2-furanyl, 3-Ethoxy-2-furanyl, 3- Furanyl, 2-Chlor-3-furanyl, 2-Brom-3-furanyl, 2-Iod-3-furanyl, 2-Cyano-3-furanyl, 2-Methyl-3- furanyl, 2-(Trifluormethyl)-3-furanyl, 2-Methoxy-3-furanyl, 2-Ethoxy-3-furanyl, 4-Chlor-5- isothiazolyl, 3,4-Dichlor-5-isothiazolyl, 2-Fluor-phenyl, 2,6-Difluor-phenyl, 2-Chor-phenyl, 2,6- Dichlor-phenyl, 2-Brom-phenyl, 2-Iod-phenyl, 2-(Difluormethyl)-phenyl, 2-(Trifluormethyl)- phenyl, 2-Chlor-3-pyridyl, 3-Chlor-2-pyridyl oder 2-(Trifluormethyl)-3-pyridyl steht;

Y für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, sec-Butyl, iso-Butyl, tert.-Butyl, Cyanomethyl, 2,2-Difluor-ethyl, 2,2,2-Trifluor-ethyl, Allyl, Butenyl, Propargyl, Butinyl, 3,3- Dichlor-prop-2-enyl, Methoxy, Ethoxy, Cyclopropylmethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl steht;

W für Sauerstoff steht;

L ¹ für -IM^R ¹ ) steht, wobei R ¹ für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Cyclopropylmethyl oder Cyclopropyl steht;

L ² für C(R ²¹ , R ²² ) steht, wobei R ²¹ und R ²² jeweils unabhängig voneinander für Wasserstoff, Fluor, Methyl, Ethyl, n-Propyl, iso-Propyl, Allyl, Propargyl, Methoxy, Ethoxy, Allyloxy, Propargyloxy, Cyclopropylmethyl, Cyclopropyl oder wobei C(R ²¹ , R ²² ) für spiro-C(CH ₂ -CH ₂ ) steht;

L ³ für eine Direktbindung zwischen L ² und N-Y steht.

In einer ganz besonders bevorzugten weiteren Ausführungsform sind Verbindungen der Formel (I-b) Verbindungen

in welcher L , L , Q, W und Y wie oben definiert sind und M' und M ³ unabhängig voneinander für Halogen, Cyano, Nitro, OH, (Ci-Go)-Alkyl, (G-Go)- Halogenalkyl, (Ci-Cio)-Alkoxy, (Ci-Cio)-Halogenalkoxy, (Ci-Cio)-Alkylthio, (G-Go)- Halogenalkylthio, (Ci-Cio)-Alkylsulfonyl, (Ci-Cio)-Halogenalkylsulfonyl, (Ci-Cio)-Alkylsulfanyl, (Ci-Cio)-Halogenalkylsulfanyl, (3- bis 14-gliedrige cyclische Gruppe)-0- ;

Neu sind die Verbindungen der Formel (I-a)

in welcher M ¹ für Chlor, Brom oder Jod steht und L ¹ , L ² , L ³ , X und Y wie oben definiert sind. Neu sind die Verbindungen der Formel 1-2

in welcher L ¹ , L ² , L ³ , X und Y wie oben definiert sind.

Neu sind die Verbindungen der Formel 1-3

in welcher L ¹ , L ² , L ³ , X und Y wie oben definiert sind.

Neu sind die Verbindungen der Formel 1-4

in welcher L ¹ , L ² , L ³ , X und Y wie oben definiert sind. Darstellungsverfahren A

o

+ Har A, Q

(a3)

Die Reste X, Y, L ¹ , L ² , L ³ , und Q haben die oben beschriebenen Bedeutungen. W steht in diesem Fall für Sauerstoff.

Erfindungsgemäße Verbindungen der allgemeinen Formel (a) können ausgehend von Aminen gemäß Formel (al) und Carbonsäuren gemäß Formel (a2) bzw. deren Halogenide gemäß Formel (a3) nach hinlänglich bekannten Verfahren dargestellt werden, beispielsweise wie in WO-A 2007/060166 beschrieben. Die Amine gemäß Formel (al) und Carbonsäuren gemäß Formel (a2) sowie deren Halogenide gemäß Formel (a3) sind kommerziell verfügbar.

Darstellungsverfahren A-l

Die Verbindungen der Formel (I-a)

in welcher M für Chlor, Brom oder Jod steht und L , L , L , X und Y wie oben definiert sind, werden hergestellt, indem Amine der Formel (al)

1 3

X L NH

I

Y

(a1 )

wobei X, Y, L ¹ , L ² , L ³ die oben beschriebenen Bedeutungen haben,

mit Carbonsäuren der Formel (a2-l)

(a2-1 ) wobei M für Chlor, Brom oder Jod steht, oder deren Säurehalogenide der Formel (a3-l)

(a3-1 )

wobei M ¹ für Chlor, Brom oder Jod und Hai für Fluor, Chlor oder Brom steht,

zu den Verbindungen der Formel (I-a) umgesetzt werden.

Die Amine gemäß Formel (al) und Carbonsäuren gemäß Formel (a2-l) sowie deren Halogenide gemäß Formel (a3-l) sind kommerziell verfügbar. Alternativ lassen sich die Halogenide gemäß Formel (a3-l) nach hinlänglich bekannten Methoden aus den Carbonsäuren gemäß Formel (a2-l) mit entsprechenden Halogenierungsreagentien herstellen, beispielsweise mit Phosphorylchlorid, Phosphorylbromid, Thionylchlorid, Oxalylchlorid oder Phosgen.

Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I-a) werden beim Einsatz von Carbonsäurehalogeniden der allgemeinen Struktur (a3-l) vorteilhafterweise in Gegenwart eines Reaktionshilfsmittels durchgeführt. Als solche kommen alle üblichen anorganischen oder organischen Basen in Frage. Hierzu gehören beispielsweise Erdalkali- oder Alkalimetallhydride, -hydroxide, -amide, alkoholate, -acetate, -carbonate oder -hydrogencarbonate, wie beispielsweise Natriumhydrid, Natriumamid, Natriummethylat, Natriumethylat, Kalium-t.-butylat, Natriumhydroxid, Kaliumhydroxid, Ammoniumhydroxid, Natriumacetat, Kaliumacetat, Calciumacetat, Ammoniumacetat, Natriumcarbonat, Kaliumcarbonat, Kaliumhydrogencarbonat, oder Ammoniumcarbonat sowie tertiäre Amine, wie beispielsweise Trimethylamin, Triethylamin, Diisopropylethylamin, Tributylamin, N,N-Dimethylanilin, Pyridin, N-Methyl-piperidin, 4-(N,N-Dimethylamino)-pyridin, Diazabicyclooctan (DABCO), Diazabicyclononen (DBN) oder Diazabicycloundecen (DBU), insbesondere Triethylamin.

Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I-a) werden beim Einsatz von Carbonsäuren der allgemeinen Struktur (a2-l) vorteilhafterweise in Gegenwart eines Kondensationsmittels durchgeführt. Die Carbonsäuren sind kommerziell verfügbar. Als Kondensationsmittel sind vor allem wasserentziehende Chemikalien geeignet. Hierzu gehören vorzugsweise Säureanhydride und Säurehalogenide, wie beispielsweise Acetanhydrid, Propionsäureanhydrid, Phosphor-(V)-oxid, Phosphorylchlorid, Phosphorylbromid, Phosportrichlorid, Phosphortribromid, Thionylchlorid, Oxalylchlorid, Phosgen, Diphosgen, Ameisensäuremethylester, Ameisensäureethylester, sowie Carbodiimide, wie beispielsweise Ν,Ν'-Dicyclohexylcarbodiimid (DCC) oder l-Ethyl-3-(3-dimethylaminopropyl)carbodiimid Hydrochlorid (EDC-HC1). Weitere bekannte Kondensationsreagenzien sind Triphenylphosphin/Tetrachlormethan, 4-(4,6-Dimethoxy[1.3.5]triazin-2- yl)-4-methyl-morpholiniumchlorid-Hydrat oder Hydroxybenzotriazol (HOBt). Insbesondere die Kombination von l-Ethyl-3-(3-dimethylaminopropyl)carbodiimid Hydrochlorid (EDC-HC1) und Hydroxybenzotriazol (HOBt) sei hier aufgeführt.

Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I-a) werden gegebenenfalls unter Einsatz eines oder mehrerer Verdünnungsmittel hergestellt. Als Verdünnungsmittel kommen vor allem inerte organische Lösungsmittel in Betracht. Hierzu gehören insbesondere aliphatische, alicylische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie beispielsweise Benzin, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Petrolether, Hexan, Cyclohexan, Dichlormethan, Chloroform, Tetrachlormethan, Tetrahydrofuran, Dioxan, Acetonitril oder Dimethylformamid.

Die Reaktionstemperaturen können bei der Durchführung des Verfahrens A-l in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen 0 °C und 150 °C, vorzugsweise zwischen 10 °C und 120 °C.

Das Verfahren A-l wird im Allgemeinen unter Normaldruck durchgeführt. Es ist aber auch möglich, das Verfahren A-l unter erhöhtem oder verminderten Druck - im Allgemeinen zwischen 0,1 bar und 10 bar - durchzuführen.

Darstellungsverfahren B

(b1 ) (a2) (b)

O

+ Hal^Q

(a3)

Die Reste X, L ¹ , L ² , L ³ , und Q haben die oben beschriebenen Bedeutungen. W steht in diesem Fall für Sauerstoff, Y steht für Wasserstoff.

Erfindungsgemäße Verbindungen der allgemeinen Struktur (I) bzw. deren Ausführungsform (b) können ausgehend von Aminen gemäß Formel (bl) und Carbonsäuren gemäß Formel (a2) bzw. deren Halogenide gemäß Formel (a3) nach hinlänglich bekannten Verfahren dargestellt werden, beispielsweise wie in EP2007060166 beschrieben. Die Amine gemäß Formel (bl) und Carbonsäuren gemäß Formel (a2) bzw. deren Halogenide gemäß Formel (a3) sind kommerziell verfügbar. Darstellungsverfahren C

(b) (a)

Die Reste X, Y, L ¹ , L ² , L ³ , und Q haben die oben beschriebenen Bedeutungen. W steht in diesem Fall für Sauerstoff, AG für Abgangsgruppe, beispielsweise Halogene oder Alkyl- bzw. Arylsulfonate.

Erfindungsgemäße Verbindungen der allgemeinen Formel (I) bzw. deren Ausführungsform (a) können ausgehend von Aminen gemäß Formel (b) und Alkylierungsmitteln gemäß Formel (cl) nach hinlänglich bekannten Verfahren dargestellt werden, beispielsweise wie in EP2007060166 beschrieben.

Darstellungsverfahren D

O ^ocler S

₁ 3 I I Lawesson Reagenz _{1 3} n x- Lr N- - x- ^L -Lr N-

I I Y Y

(a) (d)

Die Reste X, Y, L ¹ , L ² , L ³ und Q haben die oben beschriebenen Bedeutungen. W = Sauerstoff wird direkt zu W = Schwefel transformiert.

Erfindungsgemäße Verbindungen der allgemeinen Formel (I) bzw. deren Ausführungsform (d) können ausgehend von Verbindungen der Formel (a) und geeigneten Schwefelungsreagenzien, z.B. Tetraphosphordecasulfid („Phosphorpentasulfid") oder 2,4-Bis-[4-methoxyphenyl]-2,4-dithiono-l, 2,3,4- dithiadiphosphetan („Lawesson Reagenz"), nach hinlänglich bekannten Verfahren hergestellt werden. Verfahrensbeispiele sind u.a. bekannt aus Houben-Weyl, Methoden der Organischen Chemie, E5, 1255 (Thieme Verlag, Stuttgart, 1985).

Ein weiterer Aspekt der vorliegenden Erfindung ist ein Verfahren zum Bekämpfen von endoparasitären Schädlingen dadurch gekennzeichnet, dass man eine erfindungsgemäße Verbindung der Formel (I) oder (I-a) sowie deren Salze, N-Oxide und tautomere Formen auf die Schädlinge und/oder ihren Lebensraum einwirken lässt.

Anthelmintische Anwendungsgebiete

Die erfindungsgemäßen Mittel eignen sich bei günstiger Warmblütertoxizität zur Bekämpfung von pathogenen Endoparasiten, die bei Menschen und in der Tierhaltung und Tierzucht bei Nutz-, Zucht-, Zoo-, Labor-, Versuchs- und Hobbytieren vorkommen. Sie können gegen alle oder einzelne Entwicklungsstadien der Schädlinge sowie gegen resistente und normal sensible Endoparasiten-lsolate eingesetzt werden. Durch die Bekämpfung der pathogenen Endoparasiten sollen Krankheit, Todesfälle und Leistungsminderungen (z.B. bei der Produktion von Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) vermindert werden, so dass durch den Einsatz der Wirkstoffe eine wirtschaftlichere, einfachere und gesündere Tierhaltung möglich ist. Zu den pathogenen Endoparasiten zählen Helminthen wie Platyhelmintha (insbesondere Monogenea, Cestoden und Trematoden), Nematoden, Pentastoma und Acanthocephala. Als Beispiele seien genannt:

Monogenea: z.B.: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp..

Cestoden: Aus der Ordnung der Pseudophyllidea z.B.: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diphlogonoporus spp..

Aus der Ordnung der Cyclophyllida z.B.: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp..

Trematoden: Aus der Klasse der Digenea z.B.: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp-, Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp..

Nematoden: Aus der Ordnung der Trichinellida z.B.: Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp..

Aus der Ordnung der Tylenchida z.B.: Micronema spp., Strongyloides spp..

Aus der Ordnung der Rhabditina z.B.: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafüaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp. Aus der Ordnung der Spirurida z.B.: Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., Parascaris spp., Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp.; Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp.

Acantocephala: Aus der Ordnung der Oligacanthorhynchida z.B: Macracanthorhynchus spp., Prosthenorchis spp.; aus der Ordnung der Polymorphida z.B.: Filicollis spp.; aus der Ordnung der Moniliformida z.B.: Moniliformis spp.,

Aus der Ordnung der Echinorhynchida z.B. Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.

Pentastoma: Aus der Ordnung der Porocephalida z.B. Linguatula spp.

Gemäß einer bevorzugten Ausführungsform werden die Verbindungen der Formel (I) zur Bekämpfung von Nematoden eingesetzt. Als Nematoden seien besonders bevorzugt genannt: Trichinellida, Tylenchida, Rhabditina oder die folgenden aus der Ordnung der Spirurida: Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp ..

Gegenstand einer weiteren besonders bevorzugten Ausführungsform ist die Verwendung zur Bekämpfung von Strongylida, insbesondere Haemonchus spp. (z. B. Haemonchus contortus), Trichostrongylus spp. (z. B. Trichostrongylus colubriformis), Cooperia spp., und Ostertagia spp oder Teladorsagia spp..

Gegenstand einer weiteren besonders bevorzugten Ausführungsform ist die Verwendung zur Bekämpfung von Ascaridida wie z. B. Parascaris spp.

Tiere können Fische, Reptilien, Vögel oder insbesondere Säugetiere sein.

Zu den Nutz- und Zuchttieren gehören Säugetiere wie z.B. Rinder, Pferde, Schafe, Schweine, Ziegen, Kamele, Wasserbüffel, Esel, Kaninchen, Damwild, Rentiere, Pelztiere wie z.B. Nerze, Chinchilla, Waschbär, Vögel wie z.B. Hühner, Gänse, Puten, Enten, Strauße, Fische wie Forellen, Lachse, Karpfen, Barsche, Hechte, Aale.

Zu Labor- und Versuchstieren gehören Mäuse, Ratten, Meerschweinchen, Goldhamster, Hunde und Katzen.

Zu den Hobbytieren gehören Hunde und Katzen. Erfindungsgemäß bevorzugt ist die Anwendung bei Tieren, aber grundsätzlich kommt auch die Anwendung am Menschen in Frage. Vorzugsweise werden beim Menschen Ascaris spp., Ancylostoma spp, Necator spp., Trichuris spp., Strongyloides spp. und Enterobius spp. bekämpft.

Unter den Säugetieren werden gemäß einer Ausfuhrungsform für die erfindungsgemäße Anwendung die Pflanzenfresser (Herbivoren) bevorzugt, also Tiere, die sich hauptsächlich von Pflanzen ernähren. Besonders bevorzugt ist die Behandlung von Wiederkäuern (wie z. B. Schafe, Ziegen, Rinder).

Als nicht wiederkäuende Pflanzenfresser, die Säugetiere sind, seien als bevorzugtes Beispiel die Pferde genannt. Dort können die obengenannten Kombinationen bevorzugt z. B. zur Bekämpfung von Strongylida oder insbesondere von Spulwürmern (Ascaridia), wie z. B. Parascaris equorum, eingesetzt werden.

Bei den Wiederkäuern können bevorzugt Strongylida, insbesondere Haemonchus spp., Trichostrongylus spp., Cooperia spp. und Ostertagia spp. bekämpft werden.

Besonders bevorzugt werden erfindungsgemäß Schafe behandelt.

Ebenfalls besonders bevorzugt werden erfindungsgemäß Rinder behandelt.

Die Anwendung der erfindungsgemäßen Wirkstoffe erfolgt im Veterinärsektor und bei der Tierhaltung in an sich bekannter Weise direkt oder in Form von geeigneten Zubereitungen. Die Anwendung kann sowohl prophylaktisch als auch therapeutisch erfolgen.

Die Verbindungen der allgemeinen Formel (I) oder (I-a) können alleine oder in Kombination mit anderen Wirkstoffen, z. B. mit anderen Parasitiziden, eingesetzt werden.

Die folgenden Beispiele erläutern die Erfindung, ohne sie einzuschränken.

Herstellungsbeispiele:

Beispiel 14-11

94,6 mg (0,75 mmol) 2-Methylfuran-3 -carbonsäure, 198 mg (0,90 mmol) 2-(4-Chlorphenyl)-2- methylpropan-l-amin, 50,6 mg (0,37 mmol) 1 -Hydroxybenzotriazole (HOBt), 46 mg (0,37 mmol) DMAP, 172,5 mg (0,90 mmol) EDC-Hydrochlorid und 116 mg (0,90 mmol) Diisopropylethylamin werden in 10 ml Dichlormethan gelöst und bei Raumtemperatur für 16 h gerührt. Nach beendeter Reaktion wird mit 10 ml Wasser versetzt und die organische Phase abgetrennt, die wässrige Phase mit 5 ml Dichlormethan nachextrahiert. Die Dichlormethanphasen werden über eine Natriumsulfat/Kieselgelkartusch filtriert, das Lösungsmittel wird abgedampft und der Rückstand mittels präparativer HPLC getrennt.

Ausbeute: 139,3 mg (63,6 % d. Th.), farbloser Feststoff.

'H-NMR (d6-DMSO): δ [ppm], 7,73 (t, 1H, NH), 7,48 (d, 1H), 7,42 (d, 2H), 7,35 (d, 2H), 6,80 (d, 1H), 3,37 (d, 2H), 2,43 (s, 3H), 1,26 (s, 6H).

Beispiel 20-238

114 mg (0,6 mmol) 2-(2-Chlor-4-(trifluormethyl)phenoxy)-l-ethylamin, 163 mg (0,72 mmol) 2- (Trifluormethyl)-nicotinsäurechlorid, 40,5 mg (0,3 mmol) 1 -Hydroxybenzotriazole (HOBt), 36,6 mg (0,3 mmol) DMAP, 115 mg (0,6 mmol) EDC-Hydrochlorid und 77,5 mg (0,6 mmol) Diisopropylethylamin werden in 10 ml Dichlormethan gelöst und bei Raumtemperatur für 16 h gerührt. Nach beendeter Reaktion wird mit 10 ml Wasser versetzt und die organische Phase abgetrennt, die wässrige Phase mit 5 ml Dichlormethan nachextrahiert. Die Dichlormethanphasen werden über eine Natriumsulfat/Kieselgelkartusche filtriert, das Lösungsmittel wird abgedampft und der Rückstand mittels präparativer HPLC getrennt.

Ausbeute: 146 mg (59,9 % d. Th.), farbloser Feststoff.

'H-NMR (d6-DMSO): δ [ppm], 8,95 (t, 1H, NH), 8,80 - 8,79 (d, 1H), 7,99 - 7,97 (d, 1H), 7,84 (s, 1H), 7,80 - 7,77 (dd, 1H), 7,72 - 7,69 (d, 1H), 7,40 - 7,38 (d, 1H), 4,30 (t, 2H), 3,70 - 3,67 (quart, 2H).

Nachfolgende Tabellenbeispiele sind auf gleiche Weise herstellbar.

Ή-NMR Daten

Die Bestimmung der 'H-NMR-Daten erfolgte mit einem Broker Avance 400 ausgestattet mit einem Durchflussprobenkopf (60 μΐ Volumen), mit Tetramethylsilan als Referenz (0.0) und den Lösungsmitteln CD ₃ CN, CDC1 ₃ , D ₆ -DMSO.

Die NMR-Daten ausgewählter Beispiele werden entweder in klassischer Form (δ-Werte, Multiplettaufspaltung, Anzahl der H-Atome) oder als NMR-Peak-Listen aufgeführt.

NMR-Peak-Listenverfahren: Wenn die 'H-NMR-Daten ausgewählter Beispiele in Form von 'H-NMR- Peaklisten notiert werden, wird zu jedem Signalpeak erst der δ-Wert in ppm und dann die Signalintensität durch ein Leerzeichen getrennt aufgeführt. Die δ-Wert - Signalintensitäts-Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die

Peakliste eines Beispieles hat daher die Form: 8i(Intensitäti);82 (Intensität2); ;8i(Intensitäti); ;

8n(Intensität _n ). Das Lösungsmittel, in welchem das NMR-Spektrum aufgenommen wurde, wird in eckigen Klammern vor der NMR-Peakliste bzw. der klassischen NMR-lnterpretationsliste aufgeführt.

Tabelle 1

Verbindungen der Formel 1-1

Bsp.-Nr. X L ¹ L ² Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

1-1 3-methyl-2-thienyl CH ₂ CH ₂ - H WO-A 2006/108791

1 -2 2,4-dichlor-phenyl CH ₂ CH ₂ CH ₂ H WO-A 2008/101976

1 -3 4-chlor-phenyl CH ₂ CH ₂ - H CAS: 1043286-26-5

1 -4 4-chlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz

7.7469 (1.12); 7.7252 (1.15); 7.7057 (0.94); 7.6841 (0.94); 7.6179 (1.95); 7.6129 (2 7.5900 (2.33); 7.5853 (2.53); 7.5290 (3.02); 7.5166 (3.14); 7.4844 (0.67); 7.4796 (0 7.4634 (2.97); 7.4586 (3.00); 7.4477 (3.91); 7.4430 (2.06); 7.4377 (1.80); 7.4267 (1 7.4179 (2.89); 7.3969 (1.08); 6.9234 (2.11); 6.91 14 (4.42); 6.8992 (2.53); 4.7378 (1 4.7244 (1.71); 4.6260 (2.08); 4.6102 (2.30); 4.3387 (0.65); 4.3221 (1.13); 4.3180 (Ϊ 4.3049 (0.95); 4.3009 (1.21); 4.2840 (0.75); 3.3237 (7.87); 3.1838 (16.00); 3.1784 (13. 2.51 15 (4.24); 2.5072 (8.58); 2.5027 (1 1.54); 2.4982 (8.53); 2.4939 (4.20); 2.3293 (10. 2.2726 (13.26); 1.3965 (4.48); 1.1408 (5.91 ); 1.1234 (7.31 ); 1.1033 (4.64); 0.0080 (0.4

1-5 2,4-dichlor-phenyl CH(0CH3) CH(CH3) H 0.0002 (1 1.36); -0.0084 (0.44)

[DMSO], Spektrometer: 399.95MHz

7.9424 (0.59); 7.9286 (1.15); 7.9146 (0.61 ); 7.5253 (2.91 ); 7.5129 (3.03); 7.3730 (0 7.3668 (3.29); 7.3619 (1.23); 7.3506 (1.51 ); 7.3455 (6.10); 7.3396 (0.97); 7.2968 (0 7.291 1 (5.46); 7.2862 (1.62); 7.2744 (1.17); 7.2699 (3.14); 6.9182 (3.00); 6.9058 (2 3.9077 (13.77); 3.5200 (0.43); 3.3909 (365.99); 3.3564 (4.91); 3.3378 (3.29); 3.3241 (2 3.3086 (0.84); 3.3055 (0.88); 3.2918 (0.59); 3.1730 (0.70); 3.0889 (0.58); 3.0712 (1 3.0532 (1.03); 3.0349 (0.52); 2.6786 (0.40); 2.5486 (0.35); 2.5318 (1.35); 2.5184 (23 2.5140 (45.87); 2.5094 (60.62); 2.5049 (45.57); 2.5005 (23.03); 2.3362 (0.40); 2.2661 (16

1-6 4-chlor-phenyl CH(CH3) CH2 H 1.2158 (6.84); 1.1983 (6.73)

[DMSO], Spektrometer: 399.95MHz

8.0105 (0.50); 7.9962 (0.98); 7.9821 (0.49); 7.5641 (2.66); 7.5588 (2.84); 7.5264 (2 7.5140 (2.48); 7.4725 (1.36); 7.4514 (3.22); 7.4255 (1.99); 7.4202 (1.82); 7.4045 (0 7.3991 (0.80); 6.9178 (2.43); 6.9054 (2.33); 3.9098 (16.00); 3.5797 (0.40); 3.5615 (0 3.5439 (0.88); 3.5266 (0.58); 3.4821 (0.34); 3.4668 (0.44); 3.4493 (1.23); 3.4350 (1 3.4225 (1.79); 3.4184 (2.08); 3.4030 (2.01 ); 3.3667 (243.69); 3.1736 (0.54); 2.6785 (0 2.5487 (0.60); 2.5317 (1.37); 2.5183 (22.50); 2.5139 (44.62); 2.5093 (58.74); 2.5048 (44.

1-7 2,4-dichlor-phenyl CH(CH3) CH2 H 2.5003 (22.23); 2.3361 (0.37); 2.2755 (13.20); 1.2055 (5.51); 1.1882 (5.42)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr. 1-8, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8223 (1 ,2); 7,8015 (1 ,24); 7,5241 (3,1 1); 7,51 17 (3,23); 7,3417 (3,49); 7,3369 (1,32); 7, (1 ,69); 7,3205 (6,55); 7,3148 (1 ,04); 7,268 (5,53); 7,2469 (3, 16); 6,9166 (3,19); 6,9042 (3, 4, 1649 (0,58); 4,1488 (0,86); 4,1325 (0,65); 3,9091 (16); 3,3749 (344,32); 3,2939 (0, 3,1799 (0,46); 3, 1673 (0,47); 2,8526 (0,66); 2,8318 (0,66); 2,819 (1 ,42); 2,7983 (1,41); 2, (1 ,42); 2,756 (1 ,48); 2,7375 (0,68); 2,7223 (0,62); 2,6831 (0,33); 2,6785 (0,44); 2,6742 (0, 2,5486 (0,34); 2,5318 (1 ,47); 2,5184 (25,95); 2,514 (50,99); 2,5094 (66,77); 2,5049 (49, 2,5004 (24,96); 2,3407 (0,33); 2,3362 (0,44); 2,3315 (0,32); 2,2708 (15,79); 1 , 1618 (7,

1-8 4-chlor-phenyl CH2 CH(CH3) H 1 ,1453 (7,28)

1-9 2,4-dichlor-phenyl CH2 CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz

7.7190 (0.39); 7.7039 (0.75); 7.6887 (0.39); 7.5281 (2.00); 7.5157 (2.07); 7.4368 (2. 7.4316 (0.84); 7.4202 (1.10); 7.4149 (4.11); 7.4085 (0.64); 7.3725 (0.60); 7.3662 (4. 7.3608 (1.10); 7.3494 (0.82); 7.3443 (2.21); 6.91 1 1 (2.05); 6.8987 (1.99); 3.9041 (1 1. 3.4232 (3.25); 3.4074 (3.61); 3.3650 (195.16); 3.1685 (0.56); 2.5265 (0.87); 2.5130 (17. 2.5087 (34.78); 2.5041 (45.86); 2.4996 (34.77); 2.4953 (18.07); 2.2374 (10.99); 1.

1-10 4-chlor-phenyl C(CH3)2 CH2 H (16.00)

[DMSO], Spektrometer: 399.95MHz

7.7467 (0.44); 7.7315 (0.87); 7.7159 (0.43); 7.5311 (2.32); 7.5252 (2.49); 7.5174 (2. 7.5050 (2.15); 7.4758 (1.49); 7.4541 (2.25); 7.3769 (1.47); 7.3711 (1.40); 7.3554 (0. 7.3496 (0.94); 6.8988 (2.14); 6.8864 (2.07); 3.9046 (10.59); 3.7588 (2.77); 3.7430 (2. 3.3880 (1.35); 3.3535 (185.47); 3.1680 (0.59); 2.6726 (0.33); 2.5428 (0.63); 2.5257 (1. 2.5122 (20.13); 2.5080 (39.32); 2.5035 (51.69); 2.4990 (39.41); 2.4950 (20.61); 2.3302 (0.

1-11 2,4-dichlor-phenyl C(CH3)2 CH2 H 2.311 1 (0.33); 2.2063 (1 1.23); 1.4394 (16.00); -0.0002 (4.70)

[DMSO], Spektrometer: 399.95MHz

8.0508 (0.61); 8.0368 (1.15); 8.0228 (0.60); 7.5422 (2.97); 7.5298 (3.08); 7.4403 (1. 7.4361 (1.12); 7.4223 (1.81); 7.4174 (1.79); 7.3536 (0.96); 7.3480 (1.18); 7.3353 (1. 7.3303 (1.95); 7.3045 (0.60); 7.3002 (0.80); 7.2862 (1.91); 7.2819 (1.78); 7.2732 (1. 7.2672 (2.05); 7.2546 (1.53); 7.2493 (1.28); 7.2362 (0.47); 7.2311 (0.37); 6.9380 (3. 6.9255 (2.93); 3.9044 (12.08); 3.4851 (1.15); 3.4681 (2.37); 3.4523 (2.36); 3.4349 (1. 3.3627 (281.12); 3.1686 (0.45); 2.9729 (2.05); 2.9547 (3.44); 2.9371 (1.82); 2.6731 (0. 2.5260 (1.29); 2.5125 (23.55); 2.5084 (45.80); 2.5040 (60.06); 2.4995 (45.39); 2.4954 (23.

1-12 2-chlor-phenyl CH2 CH2 H 2.3422 (16.00); -0.0002 (0.79)

[DMSO], Spektrometer: 399.95MHz

8.0102 (0.60); 7.9967 (1.14); 7.9831 (0.59); 7.5613 (3.22); 7.5468 (3.04); 7.5407 (3. 7.5345 (3.17); 7.5192 (2.81); 7.5143 (2.91); 7.3199 (0.42); 7.3151 (0.40); 7.2519 (1. 7.2468 (1.59); 7.2313 (1.42); 7.2263 (1.39); 6.9403 (3.14); 6.9279 (3.02); 3.9089 (1 1. 3.4723 (1.28); 3.4551 (2.84); 3.4405 (3.05); 3.4235 (2.16); 3.3770 (275.74); 3.1735 (0. 2.8541 (1.81); 2.8369 (3.59); 2.8196 (1.60); 2.6786 (0.34); 2.5318 (1.11); 2.5184 (19. 2.5140 (39.18); 2.5094 (51.97); 2.5049 (39.10); 2.5004 (19.77); 2.3362 (0.43); 2.331 1 (0.

1-13 3 ,4-dichlor-phenyl CH2 CH2 H 2.3198 (16.00)

Verbindung Nr. 1-14, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0159 (0,55); 8,0022 (1 ,1 1); 7,9887 (0,61); 7,5485 (2,74); 7,536 (2,91); 7,4478 (1,39); 7, (2,85); 7,4383 (1 ,7); 7,3187 (6,2); 7,314 (6,04); 6,9405 (2,88); 6,9281 (2,85); 3,9076 (13,

1-14 3,5- dichlor-pheny 1 CH2 CH2 H 3,5201 (0,46); 3,4809 (1 ,61); 3,464 (3,39); 3,4494 (4,07); 3,4321 (4,33); 3,3912 (389,

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

3, 1791 (0,47); 3, 1663 (0,46); 2,8652 (1 ,72); 2,8483 (3,49); 2,8313 (1 ,59); 2,6831 (0, 2,6785 (0,45); 2,6742 (0,35); 2,5317 (1 ,51); 2,5184 (24,67); 2,514 (49,01); 2,5094 (64, 2,5048 (48,68); 2,5005 (24,91); 2,3407 (0,36); 2,3362 (0,47); 2,3316 (0,39); 2,3145 (16)

1-15 3-chlor-phenyl CH2 CH2 - H CAS: 1325308-79-9

1-16 2-fluor-phenyl CH2 CH2 - H CAS: 1240811-68-0

[DMSO], Spektrometer: 399.95MHz

7.7467 (0.44); 7.7315 (0.87); 7.7159 (0.43); 7.5311 (2.32); 7.5252 (2.49); 7.5174 (2. 7.5050 (2.15); 7.4758 (1.49); 7.4541 (2.25); 7.3769 (1.47); 7.3711 (1.40); 7.3554 (0. 7.3496 (0.94); 6.8988 (2.14); 6.8864 (2.07); 3.9046 (10.59); 3.7588 (2.77); 3.7430 (2. 3.3880 (1.35); 3.3535 (185.47); 3.1680 (0.59); 2.6726 (0.33); 2.5428 (0.63); 2.5257 (1. 2.5122 (20.13); 2.5080 (39.32); 2.5035 (51.69); 2.4990 (39.41); 2.4950 (20.61); 2.3302 (0.

1-17 2,6-difluor-phenyl CH2 CH2 H 2.311 1 (0.33); 2.2063 (1 1.23); 1.4394 (16.00); -0.0002 (4.70)

[DMSO], Spektrometer: 399.95MHz

8.1088 (0.60); 8.0946 (1.16); 8.0802 (0.61); 7.5393 (2.88); 7.5269 (3.00); 7.4613 (4. 7.441 1 (6.73); 7.2999 (2.24); 7.2807 (2.27); 7.2789 (2.1 1); 7.2596 (1.45); 6.9373 (2. 6.9249 (2.89); 3.9046 (15.92); 3.4731 (0.91); 3.4564 (2.21); 3.4389 (2.16); 3.4231 (1. 3.3464 (188.35); 3.1666 (2.10); 3.1485 (3.24); 3.1314 (1.60); 2.6723 (0.43); 2.5425 (0. 2.5254 (1.38); 2.5121 (25.86); 2.5077 (51.09); 2.5032 (67.50); 2.4986 (51.02); 2.4943 (26.

1-18 2,6-dichlor-phenyl CH2 CH2 H 2.3579 (16.00); 2.3346 (0.41); 2.3299 (0.49); 2.3255 (0.35); -0.0002 (7.67); -0.0085 (0.33)

Verbindung Nr. 1-19, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0151 (0,61); 8,0015 (1 ,13); 7,9878 (0,59); 7,5868 (2,73); 7,5694 (1 ,27); 7,5643 (2, 7,5567 (3,19); 7,5501 (3,21); 7,5399 (3,31); 7,5275 (3,32); 6,9301 (2,98); 6,9177 (2, 3,9045 (14,6); 3,5015 (1 ,06); 3,4841 (2,54); 3,4697 (2,57); 3,4524 (1 ,31); 3,428 (0,4); 3, (0,71); 3,3597 (304,29); 3,3124 (0,59); 3,3005 (0,39); 3, 1684 (0,53); 2,9509 (1 ,85); 2,

3 -(trifluormethyl)- (3,64); 2,9159 (1 ,69); 2,6731 (0,42); 2,6685 (0,32); 2,5263 (1 ,39); 2,5128 (25,41); 2,

(50,76); 2,5039 (67,15); 2,4994 (50,71); 2,495 (25,94); 2,3353 (0,33); 2,3306 (0,45); 2,

1-19 phenyl CH2 CH2 H (0,36); 2,3127 (0,68); 2,2986 (16); -0,0002 (2,03)

4-(trifluormethyl)-

1-20 phenyl CH2 CH2 H CAS: 1096213-61-4

1-21 2-methyl-phenyl CH2 CH2 - H CAS: 1328661-91-1

[DMSO], Spektrometer: 399.95MHz

8.1607 (0.39); 8.1464 (0.82); 8.1319 (0.43); 7.5696 (1.94); 7.5572 (2.04); 6.9699 (1. 6.9575 (1.94); 6.8089 (4.27); 3.9096 (10.74); 3.3940 (2.46); 3.3686 (187.69); 3.2424 (0. 3.2277 (0.94); 3.2229 (0.80); 3.2141 (0.92); 3.2071 (0.78); 3.2008 (1.00); 3.1868 (0.

2,4,6-trimethyl- 3.1739 (0.53); 2.8005 (1.09); 2.7871 (0.85); 2.7796 (1.09); 2.7744 (0.91); 2.7597 (0.

2.5488 (2.24); 2.5317 (0.96); 2.5183 (16.56); 2.5139 (33.04); 2.5094 (43.72); 2.5048 (33.

1-22 phenyl CH2 CH2 H 2.5005 (17.04); 2.4189 (10.37); 2.3362 (0.36); 2.3078 (16.00); 2.1865 (7.38)

3,4-bismethoxy-

1-23 phenyl CH2 CH2 H CAS: 1023537-11-2

1-24 phenyl CH2 CH2 - H CAS: 1090485-43-0

1-25 4-chlor-phenyl C(CH2-CH2) CH2 - H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

1-26 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

C(CH2-

1-27 4-chlor-phenyl CH2 CH2) H

C(CH2-

1-28 2,4-dichlor-phenyl CH2 CH2) H

1-29 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 1-30, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0722 (0,7); 8,0589 (1 ,33); 8,0455 (0,71); 7,5707 (4,23); 7,5637 (3,95); 7,5605 (3,47); 7, (1 ,58); 7,377 (1 ,49); 7,3613 (2, 18); 7,3548 (2, 12); 7,2495 (3,61); 7,2272 (2,64); 6,9582 (3, 6,9457 (3,03); 4,2136 (2,09); 4, 1987 (4,6); 4,1838 (2,29); 3,624 (1 ,18); 3,6095 (3,26); 3, (3,15); 3,5804 (1 ,07); 3,3333 (10,63); 2,5436 (10,77); 2,5086 (6,89); 2,5042 (9,01); 2,

1-30 2,4-dichlor-phenyl 0 CH2 CH2 H (6,82); 2,4061 (16); -0,0002 (0,4)

1-31 4-chlor-phenyl CH2 CH2 CH2 H

1-32 4-chlor-phenyl NCH3 CH2 CH2 H

1-33 2,4-dichlor-phenyl NCH3 CH2 CH2 H

1-34 4-chlor-phenyl CH(OCH3) CH2 - H

1-35 2,4-dichlor-phenyl CH(OCH3) CH2 - H

1-36 2-thienyl CH2 CH2 - H CAS: 1182416-85-8

1-37 3-thienyl CH2 CH2 - H

1-38 2-furyl CH2 CH2 - H

1-39 3-furyl CH2 CH2 - H

1-40 phenyl CH2 CH2 CH(CH3) H

1-41 phenyl CH2 CH2 CH2 H

1-42 2-Cl-phenyl CH2 CH2 CH(CH3) H

1-43 4-t-butyl-phenyl CH2 CH2 CH2 H

1-44 4-methyl-phenyl CH2 CH2 CH2 H

1-45 phenyl CH2 CH2 CH(CH2CH3) H

1-46 2-methoxy-phenyl CH2 CH2 CH2 H

1-47 2-methyl-phenyl CH2 CH2 CH2 H

1-48 3 -methyl-phenyl CH2 CH2 CH2 H

1-49 3-chlor-phenyl CH2 CH2 CH2 H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr. 1-50, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0032 (0,64); 7,9895 (1 ,2); 7,976 (0,67); 7,5479 (2,74); 7,5355 (2,88); 7,3477 (0,33); 7, (0,77); 7,3272 (0,73); 7,31 (1 ,47); 7,2922 (0,79); 7,2892 (0,97); 7,2723 (0,43); 7,0861 (1 , 7,0662 (3,26); 7,0463 (1 ,7); 6,9476 (2,95); 6,9352 (2,89); 3,332 (25,1); 3,2604 (1 ,01); 3, (2,22); 3,2273 (2,24); 3,2103 (1 ,07); 2,6829 (1 ,42); 2,6639 (2,36); 2,6444 (1 ,55); 2, (1 ,85); 2,5077 (12,73); 2,5032 (17,02); 2,4988 (13,19); 2,4284 (0,38); 2,392 (16); 1 ,

1-50 2,6-difluor-phenyl CH2 CH2 CH2 H (0,54); 1 ,7742 (1 ,43); 1,7556 (1,99); 1,737 (1 ,35); 1 ,7185 (0,48)

1-51 4-chlor-phenyl CH2 CH2 CH2 H

1-52 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

1-53 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

2,6-dimethyl-

1-54 phenyl CH2 CH2 CH2 H

1-55 2,5-dichlor-phenyl CH2 CH2 CH2 H

1-56 4-i-propoxy-phenyl CH2 CH2 CH2 H

3 -trifluormethyl-

1-57 phenyl CH2 CH2 CH(CH3) H

1-58 4-methyl-phenyl CH2 CH2 CH(CH3) H

1-59 2-methyl-phenyl CH2 CH2 CH(CH3) H

1-60 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

1-61 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

2,6-dimethyl-

1-62 phenyl CH2 CH2 CH(CH3) H

4-trifluormethyl-

1-63 phenyl CH2 CH2 CH(CH3) H

1-64 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

1-65 4-phenoxy-phenyl CH2 CH2 CH2 H

1-66 3-chlor-phenyl CH2 CH2 CH(CH3) H

1-67 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

1-68 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

2-difluormethoxy-

1-69 phenyl CH2 CH2 CH(CH3) H

1-70 4-methoxy-phenyl CH2 CH2 CH2 H

1-71 4-chlor-phenyl CH2 CH2 CH(CH3) H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

1-72 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

1-73 4-fluor-phenyl CH2 CH2 CH2 H

1-74 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

1-75 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

1-76 2-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 1-77, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0057 (0,68); 7,9926 (1 ,22); 7,9794 (0,73); 7,5501 (2,74); 7,5377 (2,9); 7,3195 (1,89); 7, (1 ,8); 7,3068 (2, 11); 7,3044 (1,92); 6,9512 (4,34); 6,9387 (4,46); 6,9303 (2,09); 6,8872 (2, 6,879 (1,86); 3,3316 (21 ,49); 3,2792 (1, 19); 3,2623 (2,71); 3,2467 (2,76); 3,2299 (1 ,28); 2 (2,03); 2,8379 (3,54); 2,8189 (2,24); 2,5412 (3,08); 2,5059 (10,76); 2,5018 (14,05); 2,

1-77 2-thienyl CH2 CH2 CH2 H (1 1, 1); 2,3973 (16); 1 ,8846 (0,64); 1 ,8663 (1,92); 1,8478 (2,61); 1 ,8296 (1 ,87); 1,81 13 (0,

1-78 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/060166

Verbindung Nr. 1-79, Solvent: [DMSO] , Spektrometer: 601.6MHz

8,0675 (0,49); 8,0583 (0,9); 8,0492 (0,47); 7,5538 (2,72); 7,5455 (2,82); 7,3741 (4,25); 7, (4,3); 6,9466 (2,8); 6,9383 (2,73); 6,9062 (2,59); 6,9049 (2,22); 6,9037 (2,52); 3,4607 (1, 3,4491 (2,45); 3,4396 (2,5); 3,4282 (1 ,1 1); 3,3253 (249); 3,3101 (0,48); 3,0195 (1,62); 3, (3,14); 3,0077 (3,17); 2,9969 (1 ,46); 2,653 (0,44); 2,6161 (0,36); 2,613 (0,49); 2,61 (0, 2,5474 (1 ,32); 2,5406 (144,26); 2,5223 (1 ,16); 2,5192 (1 ,5); 2,5161 (1,7); 2,5074 (27, 2,5044 (58,31); 2,5013 (79,87); 2,4982 (57,12); 2,4952 (26,25); 2,4245 (0,44); 2,3885 (0,

1-79 4-chlor-2-thienyl CH2 CH2 H 2,3854 (0,5); 2,3824 (0,37); 2,361 1 (16); 2,0734 (0,47); -0,0002 (5,98)

Verbindung Nr. 1-80, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0071 (0,64); 7,9933 (1 ,25); 7,9795 (0,66); 7,5515 (2,84); 7,5391 (2,93); 7, 1827 (0, 7, 1738 (4,27); 7, 1685 (1 ,41); 7, 1563 (1 ,57); 7,1511 (4,79); 7,1422 (0,51); 6,9457 (2, 6,9333 (2,88); 6,7718 (0,52); 6,763 (4,37); 6,7578 (1 ,48); 6,7403 (3,93); 6,7315 (0,44); 3, (1 ,14); 3,4596 (2,71); 3,4424 (2,18); 3,3706 (1 ,25); 3,3551 (2,37); 3,3294 (60,06); 2 (15,97); 2,5413 (14,63); 2,5063 (24,52); 2,5019 (31,42); 2,4974 (23, 16); 2,3739 (16); -0,

1-80 4-chlor-phenyl N(CH3) CH2 CH2 H (4,01)

Tabelle 2

Verbindungen der Formel 1-2

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: Ή-NMR, 0 [ppm] oder CAS- bzw. Patent-Nr.

2-1 3 -methyl-2-thieny 1 CH2 CH2 - H

Verbindung Nr. 2-2. Solvent: [DMSO], Spektrometer: 399.95MHz

8,2026 (1 ,69); 8, 1889 (3.1 1 ); 8,175 (1 ,67); 7,8265 (15,43); 7,8133 (16); 7.8078 (0,37); 7,7959 (0,51); 7.7828 (0,47); 7,5677 (10, 13); 7,5624 (10,39); 7.426 (5.49); 7,4053 (12,99); 7,3899 (0.44); 7,3803 (9,6); 7,375 (8,72); 7,3597 (3,95); 7.3544 (3,92); 7,1753 (0,46); 7, 1623 (0.47); 7,1448 (15,95); 7, 1316 (15,49); 3,5143 (0.38); 3,3561 (0,39); 3,3331 (88,56); 3,3198 (3,62); 3,3029 (7,61); 3,2879 (7,63); 3.2708 (3,31); 2,7545 (5,62); 2,7357 (6,9); 2,7158 (6,03); 2,6737 (0,32); 2,544 (14,87); 2,5272 (0,83); 2,5224 (1 ,34); 2,5138 (17, 13); 2,5092 (34,25); 2,5046 (45,37); 2,5 (32,77); 2,4954 (15,38); 2,4798 (0,32); 1 ,8378 (1 ,65); 1 ,8198 (4,34); 1 ,8009 (5,53);

2-2 2,4-dichlor-phenyl CH2 CH2 CH2 H 1 ,7822 (4,18); 1,7644 (1 ,46); -0,0002 (5,49)

[DMSO], Spektrometer: 399.95MHz 8.1377 (0.63); 8.1240 (1.15); 8.1 101 (0.62); 7.8208 (4.47); 7.8077 (4.66); 7.3703 (0.45); 7.3642 (3.96); 7.3594 (1.50); 7.3482 (1.84); 7.3431 (6.97); 7.3374 (1.07): 7.2906 (0.99); 7.2846 (5.75); 7.2636 (3.41); 7.1343 (4.73); 7.121 1 (4.56); 3.9045 (16.00); 3.5002 (1.31 ); 3.4829 (2.58); 3.4676 (2.57); 3.4498 (1.53); 3.3619 (349.85); 2.8484 (2.20); 2.8302 (3.85); 2.8125 ( 1.98); 2.6776 (0.36); 2.6732 (0.49); 2.6688 (0.37); 2.5428 (0.32); 2.5264 (1.67); 2.5130 (29.09); 2.5086 (57.80); 2.5041 (76.53); 2.4995 (57.82); 2.4951 (29.49); 2.3352 (0.34); 2.3308 (0.47); 2.3263

2-3 4-chlor-phenyl CH2 CH2 H (0.34); -0.0002 (1.25)

[DMSO], Spektrometer: 399.95MHz 8.2030 (0.50); 8.1889 (0.94); 8.1751 (0.49); 7.8178 (3.44); 7.8046 (3.60); 7.5878 (2.92); 7.3744 (6.79); 7.3714 (7.04); 7.1316 (3.64); 7.1 185 (3.50); 3.9048 (16.00); 3.5280 (0.84); 3.5108 (2.14); 3.4957 (2.20); 3.4786 (0.89); 3.3931 (0.50); 3.3501 (207.99); 2.9699 (1.74); 2.9525 (3.42); 2.9352 (1.57); 2.6726 (0.42); 2.5258 (1.38); 2.5210 (2.13); 2.5124 (24.91); 2.5080 (49.70); 2.5035 (65.74); 2.4989 (49.43);

2-4 2,4-dichlor-phenyl CH2 CH2 H 2.4945 (25.13); 2.3303 (0.40); -0.0002 (7.89)

Verbindung Nr. 2-5, Solvent: [DMSO], Spektrometer: 399.95MHz 7,8969 (0,63); 7,8755 (0,65); 7,8395 (1 ,08); 7,8263 (1 ,16); 7,8054 (1 ,55); 7,7922 (1 ,61); 7,7428 (0,45); 7,7222 (0,45); 7,4341 (2,31); 7,4133 (3,65); 7,3501 (4,24); 7,329 (2,67); 7, 1597 (1 , 12); 7, 1465 (1 ,1); 7, 1166 (1 ,63); 7, 1034 (1 ,57); 4,3685 (0,72); 4,3558 (0,82); 4,314 (1 ,05); 4,2984 (1 ,23); 4,162 (0,32); 4, 1446 (0,41 ):

2-5 4-chlor-phenyl CH(OCH3) CH(CH3) H 4, 1279 (0,52); 4, 1231 (0,42); 4, 1 1 12 (0,37); 4, 1065 (0,49); 3,3228 (9,49); 3,2061

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(13,22); 2,5066 (21,23); 2,5023 (27,41); 2,498 (20,75); 1 ,3974 (16); 1 ,137 (3,55); 1 ,1202 (3,54); 1,0942 (2,48); 1 ,0773 (2,42); -0,0002 (4,23)

2-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz 8.0473 (0.68); 8.0332 (1.28); 8.0193 (0.67); 7.8099 (4.58); 7.7967 (4.74); 7.3752 (3.64); 7.3703 (1.40); 7.3590 (1.82); 7.3539 (7.44); 7.3483 (1.19); 7.3161 (1.22); 7.3107 (6.66); 7.3059 (1.87); 7.2941 (1.36); 7.2894 (3.39); 7.1195 (4.85); 7.1063 (4.69); 3.9091 (16.00); 3.5090 (0.43); 3.4617 (0.56); 3.4429 (0.79); 3.4235 (3.81); 3.4050 (6.69); 3.3749 (417.79); 3.1730 (0.36); 3.0954 (0.67); 3.0774 (1.33); 3.0595 (1.26); 3.0415 (0.62); 2.6831 (0.38); 2.6787 (0.51); 2.6743 (0.39); 2.5319 (1.66); 2.5184 (30.26); 2.5141 (60.39); 2.5096 (80.29); 2.5050 (60.84); 2.5007 (31.19);

2-7 4-chlor-phenyl CH(CH3) CH2 H 2.3409 (0.35); 2.3363 (0.49); 2.3319 (0.36); 1.2350 (8.14); 1.2175 (7.98)

[DMSO], Spektrometer: 399.95MHz 7.7974 (0.68); 7.7842 (0.70); 7.5640 (0.54); 7.5587 (0.58); 7.4626 (0.64); 7.4268 (0.40); 7.4214 (0.37); 7.1 100 (0.71); 7.0969 (0.68); 3.9045 (2.32); 3.5640 (0.34); 3.5473 (0.38); 3.5315 (0.46); 3.5182 (0.47); 3.5010 (0.76); 3.4291 (90.98); 2.5185 (4.75); 2.5141 (9.59); 2.5096 (12.81); 2.5050 (9.84); 2.5008 (5.14); 2.0747 (16.00);

2-8 2,4-dichlor-phenyl CH(CH3) CH2 H 1.2220 (1.09); 1.2053 (1.08)

[DMSO], Spektrometer: 399.95MHz 7.9630 (1.22); 7.9424 (1.27); 7.7924 (4.06); 7.7793 (4.26); 7.3425 (3.49); 7.3378 (1.39); 7.3214 (6.93); 7.2752 (5.94); 7.2542 (3.24); 7.11 19 (4.30); 7.0988 (4.20); 4.1713 (0.69); 4.1548 (0.99); 4.1385 (0.75); 4.1 185 (0.38); 3.9043 (16.00); 3.4470 (0.40); 3.4286 (0.51); 3.3617 (361.09); 3.3140 (0.82); 3.1746 (0.46); 3.1619 (0.45); 2.8637 (0.63); 2.8435 (0.60); 2.8301 (1.62); 2.8098 (1.65); 2.7957 (1.67); 2.7803 (1.68); 2.7619 (0.65); 2.7468 (0.57); 2.6776 (0.40); 2.6731 (0.53); 2.6688 (0.41); 2.5262 (1.75); 2.5126 (30.67); 2.5085 (59.88); 2.5040 (78.76); 2.4995 (59.69); 2.4953 (30.88); 2.3350 (0.34); 2.3308 (0.48); 2.3263 (0.35); 1.1737 (7.79); 1.1572

2-9 4-chlor-phenyl CH2 CH(CH3) H (7.72)

2-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz 7.8225 (2.75); 7.8093 (2.84); 7.7385 (0.36); 7.7237 (0.69); 7.7085 (0.36); 7.4631 (2.23); 7.4580 (0.84); 7.4467 (1.16); 7.4413 (3.99); 7.4348 (0.60); 7.3929 (0.56); 7.3863 (4.17); 7.381 1 (1.11); 7.3696 (0.83); 7.3645 (2.30); 7.1202 (2.88); 7.1070 (2.78); 3.9093 (12.17); 3.4869 (2.95); 3.4713 (2.90); 3.3711 (239.20); 2.6784 (0.32); 2.5317 (1.02); 2.5183 (19.59); 2.5139 (38.92); 2.5093 (51.34); 2.5048

2-11 4-chlor-phenyl C(CH3)2 CH2 H (38.69); 2.5004 (19.81); 2.3361 (0.32); 1.3129 (16.00)

[DMSO], Spektrometer: 399.95MHz 7.8018 (3.13); 7.7887 (3.37); 7.7824 (0.47); 7.7666 (0.75); 7.7601 (0.43); 7.7512 (0.38); 7.5497 (2.38); 7.5439 (2.59); 7.4931 (1.53); 7.4714 (2.29); 7.3916 (1.64); 7.3857 (1.53); 7.3700 (1.12); 7.3641 (1.06); 7.0969 (3.23); 7.0837 (3.14); 3.9046 (14.38); 3.8154 (2.85); 3.7997 (2.83); 3.3628 (255.22); 2.6733 (0.37); 2.5266 (1.14); 2.5132 (21.80); 2.5088 (43.66); 2.5042 (57.88); 2.4997 (43.56); 2.4952

2-12 2,4-dichlor-phenyl C(CH3)2 CH2 H (22.23); 2.3310 (0.35); 1.4615 (16.00)

2-13 2-chlor-phenyl CH2 CH2 - H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz 8.1577 (0.61); 8.1436 (1.18); 8.1300 (0.67); 7.8199 (4.18); 7.8067 (4.38); 7.5614 (3.47); 7.5408 (4.24); 7.5347 (3.30); 7.5299 (3.39); 7.2628 (1.76); 7.2577 (1.77); 7.2422 (1.58); 7.2372 (1.57); 7.1321 (4.41); 7.1 189 (4.29); 3.9046 (16.00); 3.5177 (1.16); 3.5006 (2.96); 3.4857 (3.01); 3.4688 (1.33); 3.4388 (0.42); 3.3608 (347.14); 3.1740 (0.40); 3.1622 (0.37); 2.8642 (2.11); 2.8470 (4.26); 2.8297 (1.93); 2.6779 (0.41); 2.6732 (0.53); 2.6688 (0.41); 2.5433 (0.40); 2.5264 (1.84); 2.5128 (31.80); 2.5086 (61.69); 2.5041 (80.66); 2.4996 (60.63); 2.4954 (31.03); 2.3351 (0.36);

2-14 3 ,4-dichlor-phenyl CH2 CH2 H 2.3309 (0.51); 2.3264 (0.37); -0.0002 (5.83)

2-15 3,5- dichlor-pheny 1 CH2 CH2 - H

[DMSO], Spektrometer: 399.95MHz 8.1445 (0.64); 8.1314 (1.17); 8.1183 (0.66); 7.8222 (4.54); 7.8090 (4.73); 7.3499 (1.14); 7.3308 (5.66); 7.31 15 (2.92); 7.2829 (2.38); 7.2782 (1.74); 7.2661 (0.88); 7.2627 (1.07); 7.2582 (0.70); 7.2282 (2.15); 7.2098 (1.50); 7.1341 (4.89); 7.1210 (4.79); 3.9043 (16.00); 3.5172 (1.29); 3.4998 (2.92); 3.4849 (3.21); 3.4675 (1.70); 3.4498 (0.41); 3.4387 (0.56); 3.3658 (387.37); 3.3078 (0.78); 3.2857 (0.39); 3.1739 (0.33); 2.8676 (2.33); 2.8499 (4.45); 2.8322 (2.20); 2.6779 (0.38); 2.6734 (0.54); 2.6690 (0.39); 2.5266 (1.74); 2.5132 (30.49); 2.5088 (60.36); 2.5043 (79.79); 2.4998 (60.13); 2.4954 (30.62); 2.3356 (0.37); 2.3311 (0.51); 2.3266 (0.38); -

2-16 3-chlor-phenyl CH2 CH2 H 0.0002 (0.33)

[DMSO], Spektrometer: 399.95MHz 8.1933 (0.69); 8.1795 (1.28); 8.1656 (0.73); 7.8226 (4.66); 7.8095 (4.87); 7.3443 (0.89); 7.3294 (1.55); 7.3251 (1.90); 7.3063 (1.47); 7.2930 (0.53); 7.2881 (1.10); 7.2736 (1.12); 7.2679 (1.39); 7.2636 (0.79); 7.2542 (0.78); 7.2498 (0.65); 7.1803 (1.50); 7.1596 (3.1 1); 7.1432 (2.78); 7.1405 (2.70); 7.1363 (6.30); 7.1231 (5.81); 3.9084 (16.00); 3.5173 (1.70); 3.5002 (3.08); 3.4843 (3.12); 3.4669 (1.92); 3.3799 (457.67); 3.2922 (0.60); 3.1793 (0.73); 3.1668 (0.69); 2.9003 (2.23); 2.8823 (4.00); 2.8645 (2.04); 2.6830 (0.41); 2.6785 (0.55); 2.6740 (0.41); 2.5485 (0.41); 2.5315 (1.86); 2.5181 (31.81); 2.5139 (62.45); 2.5094 (82.23); 2.5049 (62.52); 2.3405

2-17 2-fluor-phenyl CH2 CH2 H (0.38); 2.3361 (0.52); 2.3315 (0.39)

[DMSO], Spektrometer: 399.95MHz 7.8107 (0.99); 7.7975 (1.05); 7.3236 (0.37); 7.1264 (1.05); 7.1132 (1.03); 7.0797 (0.51); 7.0599 (0.82); 7.0399 (0.45); 3.9037 (3.15); 3.4886 (0.91); 3.4718 (1.79); 3.4204 (120.43); 2.9156 (0.41); 2.8983 (0.78); 2.881 1 (0.38); 2.5302 (0.44); 2.5170 (6.82); 2.5126 (13.44); 2.5081 (17.68); 2.5035 (13.27); 2.4992 (6.71); 2.0740

2-18 2,6-difluor-phenyl CH2 CH2 H (16.00)

[DMSO], Spektrometer: 399.95MHz 8.2795 (0.51); 8.2654 (0.95); 8.2512 (0.49); 7.8182 (3.62); 7.8050 (3.75); 7.4669 (4.20); 7.4468 (5.88); 7.3079 (2.06); 7.2888 (2.09); 7.2868 (1.90); 7.2677 (1.33); 7.1346 (3.78); 7.1214 (3.63); 3.9095 (16.00); 3.5349 (0.88); 3.5183 (2.14); 3.5022 (2.18); 3.4853 (1.14); 3.3672 (282.29); 3.1867 (1.81); 3.1690 (3.28); 3.1517 (1.47); 2.6784 (0.42); 2.5317 (1.42); 2.5183 (25.31); 2.5139 (50.14); 2.5093 (65.95);

2-19 2,6-dichlor-phenyl CH2 CH2 H 2.5048 (49.33); 2.5004 (24.84); 2.3361 (0.42)

3 -(trifluormethyl)- [DMSO], Spektrometer: 399.95MHz

8.1552 (0.57); 8.1420 (1.01); 8.1284 (0.54); 7.8190 (3.83); 7.8058 (3.95); 7.6056

2-20 phenyl CH2 CH2 H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(2.31); 7.5919 (0.86); 7.5829 (0.97); 7.5682 (4.08); 7.5548 (2.45); 7.5421 (0.96); 7.5310 (0.48); 7.5185 (0.32); 7.1293 (4.02); 7.1 161 (3.87); 3.9045 (16.00); 3.5536 (1.08); 3.5363 (2.64); 3.5216 (2.73); 3.5044 (1.32); 3.3692 (384.74); 3.1744 (0.37); 3.1628 (0.33); 2.9655 (1.88); 2.9481 (3.71); 2.9307 (1.71); 2.6783 (0.36); 2.6740 (0.49); 2.6693 (0.36); 2.5271 (1.74); 2.5137 (30.05); 2.5093 (59.74); 2.5047 (79.00); 2.5002 (59.85); 2.4958 (30.81); 2.3359 (0.37); 2.3314 (0.52); 2.3270 (0.39)

[DMSO], Spektrometer: 399.95MHz 8.1817 (0.49); 8.1676 (0.91); 8.1538 (0.48); 7.8205 (3.55); 7.8074 (3.67); 7.6734 (2.50); 7.6532 (3.05); 7.4918 (2.75); 7.4718 (2.26); 7.1329 (3.74); 7.1197 (3.60); 3.9045 (16.00); 3.5502 (0.98); 3.5329 (2.08); 3.5177 (2.07); 3.5002 (1.15); 3.4504

4-(trifluormethyl)- (0.42); 3.3701 (329.49); 3.3107 (0.59); 3.1687 (0.49); 2.9563 (1.43); 2.9385 (2.63);

2.9208 (1.28); 2.6740 (0.41); 2.5440 (0.34); 2.5272 (1.46); 2.5138 (24.76); 2.5094

2-21 phenyl CH2 CH2 H (49.66); 2.5048 (65.83); 2.5003 (49.54); 2.4958 (25.02); 2.3316 (0.42)

[DMSO], Spektrometer: 399.95MHz 8.2055 (0.56); 8.1914 (1.03); 8.1774 (0.57); 7.8320 (4.41); 7.8188 (4.61); 7.1771 (0.88); 7.1689 (1.69); 7.1554 (3.06); 7.1467 (6.97); 7.1392 (1.32); 7.1335 (5.44); 7.1284 (3.20); 7.1252 (3.44); 7.1159 (2.95); 7.1098 (1.36); 7.1039 (1.71); 3.9042 (14.10); 3.4495 (1.45); 3.4344 (2.40); 3.4312 (2.13); 3.4261 (1.89); 3.4160 (2.67); 3.41 14 (3.29); 3.3961 (4.40); 3.3681 (316.33); 3.3082 (0.66); 3.2853 (0.33); 3.1749 (0.37); 3.1622 (0.37); 2.8482 (2.20); 2.8286 (2.58); 2.8100 (1.99); 2.6780 (0.33); 2.6736 (0.46); 2.6690 (0.34); 2.5268 (1.44); 2.5134 (25.01); 2.5090 (49.94); 2.5044

2-22 2-methyl-phenyl CH2 CH2 H (65.99); 2.4998 (49.40); 2.4954 (24.78); 2.3244 (16.00); -0.0002 (5.37)

[DMSO], Spektrometer: 399.95MHz 8.3362 (0.37); 8.3218 (0.76); 8.3073 (0.39); 7.8493 (2.28); 7.8361 (2.39); 7.1654 (2.37); 7.1522 (2.31); 6.8107 (4.16); 3.9088 (8.26); 3.3796 (236.40); 3.2968 (0.78); 3.2819 (1.10); 3.2684 (1.01); 3.2614 (0.85); 3.2551 (1.02); 3.2410 (0.74); 3.1736

2,4,6-trimethyl- (0.50); 2.8176 (1.08); 2.8040 (0.84); 2.7966 (1.09); 2.7767 (0.93); 2.5316 (1.03);

2.5180 (16.89); 2.5140 (33.01); 2.5095 (43.47); 2.5050 (32.99); 2.5007 (17.03);

2-23 phenyl CH2 CH2 H 2.3364 (0.34); 2.3086 (16.00); 2.1862 (7.13)

[DMSO], Spektrometer: 399.95MHz 8.0798 (0.48); 8.0658 (0.95); 8.0519 (0.52); 7.8244 (3.04); 7.81 12 (3.20); 7.1400 (3.23); 7.1268 (3.15); 6.8786 (2.01); 6.8582 (2.84); 6.8405 (2.24); 6.8359 (2.53); 6.7659 (1.43); 6.7612 (1.32); 6.7456 (1.05); 6.7408 (0.98); 3.9041 (10.94); 3.7302 (15.17); 3.7118 (16.00); 3.4897 (1.07); 3.4726 (1.98); 3.4550 (2.16); 3.4389 (1.82);

3,4-bismethoxy- 3.3794 (338.51); 3.1752 (0.59); 3.1627 (0.56); 2.7848 (1.52); 2.7663 (2.52); 2.7485

(1.40); 2.6744 (0.40); 2.5275 (1.29); 2.5140 (22.66); 2.5097 (44.97); 2.5052

2-24 phenyl CH2 CH2 H (59.64); 2.5007 (45.41); 2.4964 (23.63); 2.3318 (0.37)

[DMSO], Spektrometer: 399.95MHz 7.8131 (0.94); 7.7999 (0.98); 7.2995 (0.82); 7.2815 (0.86); 7.2536 (1.09); 7.2366 (0.51); 7.2041 (0.44); 7.1292 (1.00); 7.1160 (0.98); 3.8956 (2.67); 3.5033 (0.61); 3.4857 (1.00); 3.4706 (1.25); 3.4669 (1.37); 3.4512 (1.93); 3.4109 (103.28); 2.8478 (0.54); 2.8288 (0.80); 2.8109 (0.49); 2.5087 (5.66); 2.5044 (1 1.35); 2.4998 (15.07);

2-25 phenyl CH2 CH2 H 2.4953 (1 1.41); 2.4910 (5.85); 2.0658 (16.00)

C(CH2-

2-26 4-chlor-phenyl CH2) CH2 H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

C(CH2-

2-27 2,4-dichlor-phenyl CH2) CH2 H

C(CH2-

2-28 4-chlor-phenyl CH2 CH2) H

C(CH2-

2-29 2,4-dichlor-phenyl CH2 CH2) H

2-30 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 2-31, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2015 (2,25); 8, 1882 (4,21); 8,1747 (2,31); 7,8594 (12,24); 7,8462 (12,76); 7,8257 (0,4); 7,8126 (0,38); 7,5737 (10,75); 7,5672 (1 1,64); 7,3865 (5,52); 7,38 (5,32); 7,3643 (7,63); 7,3579 (7,46); 7,2503 (12,26); 7,2281 (9,04); 7,193 (0,39); 7,18 (0,4); 7, 1629 (12,99); 7, 1498 (12,64); 4,2325 (7,21); 4,2179 (16); 4,2033 (8, 11); 3,6922 (4); 3,6779 (1 1,3); 3,6635 (1 1 ,02); 3,649 (3,76); 3,3342 (54,47); 2,5446 (1 ,72); 2,5275 (0,63); 2,514 (13, 13); 2,5098 (26,04); 2,5054 (34,67); 2,5009

2-31 2,4-dichlor-phenyl 0 CH2 CH2 H (26,43); 2,4969 (13,89); -0,0002 (1 ,22)

2-32 4-chlor-phenyl CH2 CH2 CH2 H

2-33 4-chlor-phenyl NCH3 CH2 CH2 H

2-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

2-35 4-chlor-phenyl CH(OCH3) CH2 - H

2-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 2-37, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1958 (2,47); 8, 1831 (4,27); 8,1699 (2,52); 7,8355 (1 1 ,56); 7,8223 (12,07); 7,802 (0,38); 7,7886 (0,35); 7,357 (7,35); 7,3549 (7,31); 7,3443 (8,02); 7,3422 (7,7); 7, 1756 (0,39); 7, 1625 (0,44); 7,1454 (12,37); 7, 1322 (12,09); 6,974 (5,53); 6,9653 (8,64); 6,9618 (5,98); 6,9529 (8,04); 6,9286 (9,27); 6,9216 (6,48); 3,528 (4,5); 3,5104 (10,49); 3,4953 (10,88); 3,4777 (5,35); 3,3282 (51,56); 3,0758 (9,06); 3,0578 (16); 3,0399 (7,9); 2,6707 (0,4); 2,5413 (3,35); 2,5407 (3,34); 2,5056

2-37 2-thienyl CH2 CH2 H (48,75); 2,5015 (63,37); 2,4974 (49,66); 2,3282 (0,42); -0,0002 (1 ,08)

2-38 3-thienyl CH2 CH2 - H

2-39 2-furyl CH2 CH2 - H

2-40 3-furyl CH2 CH2 - H

Verbindung Nr. 2-41, Solvent: [DMSO], Spektrometer: 399.95MHz-7,9928 (2,22); 7,9721 (2,24); 7,8193 (7,33); 7,8061 (7,61); 7,2931 (2,88); 7,2744 (7,63); 7,256 (6,79); 7,2108 (8,88); 7,1928 (5,41); 7,1907 (5,41); 7,1679 (3,85); 7,1465 (8,46); 7, 1334 (7,49); 3,9791 (0,57); 3,9589 (1 ,26); 3,9434 (1 ,66); 3,928 (1 ,31); 3,9073 (0,6); 3,3467 (186, 19); 2,7002 (0,45); 2,6853 (0,67); 2,6766 (0,76); 2,6662 (1 ,84); 2,6512 (1 ,83); 2,642 (3,39); 2,6255 (3,16); 2,6186 (2,03); 2,6014 (1 ,79);

2-41 phenyl CH2 CH2 CH(CH3) H 2,59 (0,61); 2,5843 (0,7); 2,5671 (0,65); 2,5426 (34,53); 2,5257 (0,87); 2,5078

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(29,8); 2,5033 (39,32); 2,4989 (29,92); 2,0742 (0,39); 1,8911 (0,44); 1,8759 (0,54); 1,8687 (0,78); 1,8565 (1,22); 1,8426 (1,11); 1,8344 (1,66); 1,8206 (1,37); 1,8132 (1,08); 1,7978 (0,88); 1,7922 (0,95); 1,7757 (1,36); 1,7677 (1,03); 1,7612 (1,35); 1,7538 (1,35); 1,7372 (1,15); 1,7278 (0,59); 1,72 (0,61); 1,7037 (0,39); 1,179 (16); 1,1625 (15,89); 0,0079 (0,51); -0,0002 (12,6); -0,0081 (0,51)

Verbindung Nr.2-42, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1619 (2,22); 8,1492 (3,77); 8,1364 (2,21); 7,8225 (12,02); 7,8093 (12,51); 7,7925 (0,43); 7,7793 (0,36); 7,3039 (4,87); 7,2852 (13,51); 7,2669 (12,29); 7,2291 (16); 7,2116 (8,86); 7,1958 (4,5); 7,1778 (6,66); 7,1601 (2,64); 7,1434 (12,73); 7,1302 (12,26); 3,33 (81,78); 3,2909 (4,21); 3,2739 (9,58); 3,2585 (9,62); 3,2414 (4,44); 2,6714 (0,55); 2,6501 (7,43); 2,6312 (11,09); 2,6116 (7,94); 2,5417 (52,11); 2,5067 (44,47); 2,5024 (57,75); 2,4981 (43,9); 2,3293 (0,35); 2,0751 (0,66); 1,8583 (2,34); 1,8398 (6,48); 1,8211 (8,65); 1,8026 (6,12); 1,7845 (2,02); 0,0079 (0,66); -0,0002

2-42 phenyl CH2 CH2 CH2 H (16,13); -0,0083 (0,63)

2-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

2-44 4-t-butyl-phenyl CH2 CH2 CH2 H

2-45 4-methyl-phenyl CH2 CH2 CH2 H

2-46 phenyl CH2 CH2 CH(CH2CH3) H

2-47 2-methoxy-phenyl CH2 CH2 CH2 H

2-48 2-methyl-phenyl CH2 CH2 CH2 H

2-49 3 -methyl-phenyl CH2 CH2 CH2 H

2-50 3-chlor-phenyl CH2 CH2 CH2 H

2-51 2,6-difluor-phenyl CH2 CH2 CH2 H

2-52 4-chlor-phenyl CH2 CH2 CH2 H

2-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

Verbindung Nr. 2-54, Solvent: [DMSO], Spektrometer: 399.95MHz-7,9656 (2,6); 7,9449 (2,62); 7,8261 (7,86); 7,8129 (8,13); 7,4001 (3,5); 7,3956 (6,47); 7,3909 (3,83); 7,2997 (13,96); 7,295 (12,97); 7,1477 (8,13); 7,1345 (7,85); 3,9691 (0,58); 3,9485 (1,26); 3,934 (1,62); 3,9182 (1,33); 3,8974 (0,61); 3,3344 (29,05); 2,7154 (0,49); 2,7002 (0,6); 2,6924 (0,58); 2,6807 (1,87); 2,6595 (3,09); 2,6431 (3,84); 2,6217 (1,81); 2,6051 (0,63); 2,5872 (0,47); 2,5454 (21,6); 2,5145 (7,6); 2,5105 (14,83); 2,506 (19,57); 2,5015 (14,69); 2,4975 (7,45); 2,0793 (0,86); 1,8865 (0,37); 1,8709 (0,49); 1,8645 (0,77); 1,8518 (1,18); 1,8373 (1,16); 1,8304 (1,93); 1,8152 (1,77); 1,8089 (2); 1,7926 (2,06); 1,7856 (1,23); 1,7776 (1,53); 1,7725 (1,48); 1,7552 (1,24); 1,7441 (0,53); 1,7383 (0,52); 1,7349 (0,49); 1,721 (0,32);

2-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H 1,1772 (16); 1,1607 (15,86); -0,0002 (6,07)

2,6-dimethyl- Verbindung Nr.2-55, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3181 (2,09); 8,2061 (3,02); 8,1928 (5,42); 8,1793 (3); 7,8283 (14,21); 7,8152

2-55 phenyl CH2 CH2 CH2 H (14,72); 7,7982 (0,55); 7,785 (0,44); 7,5008 (13,04); 7,4945 (13,66); 7,4607

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(11,99); 7,4393 (16); 7,4263 (0,41); 7,3226 (8,63); 7,3162 (8,14); 7,3012 (6,51); 7,2948 (6,08); 7,177 (0,45); 7,164 (0,52); 7,1465 (14,9); 7,1334 (14,36); 3,3364 (121,82); 3,3094 (12,94); 3,2937 (12,47); 3,2771 (5,11); 2,7645 (8,71); 2,7458 (12,16); 2,7259 (9,31); 2,6742 (0,47); 2,5447 (42,98); 2,5094 (42,43); 2,5053 (54,42); 2,5012 (42,03); 2,3321 (0,36); 2,0782 (1,56); 1,8532 (2,58); 1,8355 (7,45); 1,8163 (9,57); 1,7978 (7,17); 1,7802 (2,28); -0,0002 (8,32)

2-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

2-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

Verbindung Nr.2-58, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3199 (0,91); 8,0068 (2,56); 7,9862 (2,54); 7,8258 (7,05); 7,8126 (7,3); 7,6239 (0,33); 7,5712 (5,61); 7,5578 (1,06); 7,5285 (15,03); 7,5018 (0,46); 7,4925 (0,48); 7,1496 (7,32); 7,1365 (7,06); 3,9918 (0,56); 3,9715 (1,26); 3,9561 (1,64); 3,941 (1,32); 3,9204 (0,61); 3,3349 (49,97); 3,3111 (0,7); 2,8065 (0,46); 2,7918 (0,64); 2,7825 (0,64); 2,772 (1,75); 2,7575 (1,88); 2,7481 (3,46); 2,7316 (3,2); 2,7249 (2,16); 2,7074 (1,8); 2,6961 (0,63); 2,6903 (0,69); 2,6734 (0,69); 2,5447 (25,9); 2,5097 (21,29); 2,5053 (27,97); 2,501 (21,36); 2,0779 (0,48); 1,9173 (0,38); 1,9022 (0,5); 1,8946 (0,74); 1,8825 (1,2); 1,8689 (1,17); 1,8605 (1,74); 1,8464 (1,52);

3 -trifluormethyl- 1,8387 (1,23); 1,8323 (1,15); 1,8158 (1,52); 1,8079 (1,18); 1,8015 (1,5); 1,7944

(1,48); 1,7778 (1,23); 1,7681 (0,59); 1,7605 (0,58); 1,7441 (0,37); 1,2098 (0,47);

2-58 phenyl CH2 CH2 CH(CH3) H 1,1881 (16); 1,1716 (15,82); 0,0079 (0,33); -0,0002 (7,99); -0,0082 (0,33)

2-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

2-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

Verbindung Nr.2-61, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3183 (0,58); 7,9722 (2,55); 7,9515 (2,58); 7,8231 (7,37); 7,81 (7,6); 7,5329 (6,66); 7,5227 (0,38); 7,5123 (7,64); 7,4972 (6,4); 7,4924 (6,61); 7,227 (3,66); 7,2222 (3,6); 7,2064 (3,23); 7,2016 (3,16); 7,1458 (7,72); 7,1326 (7,5); 3,9633 (0,57); 3,9427 (1,24); 3,928 (1,62); 3,9124 (1,33); 3,8917 (0,6); 3,3365 (67,26); 3,313 (0,61); 2,7069 (0,4); 2,6917 (0,6); 2,6838 (0,59); 2,6722 (1,93); 2,6509 (2,99); 2,6345 (3,91); 2,6137 (1,84); 2,5968 (0,64); 2,579 (0,51); 2,5446 (23,11); 2,5272 (0,55); 2,5096 (19,92); 2,5052 (26,41); 2,5007 (20,02); 2,0781 (0,85); 1,8847 (0,39); 1,869 (0,51); 1,8628 (0,82); 1,8497 (1,2); 1,8406 (0,78); 1,8354 (1,14); 1,8287 (1,93); 1,8137 (1,66); 1,8072 (1,27); 1,7996 (1,1); 1,7914 (1,12); 1,7826 (1,43); 1,7765 (1,14); 1,7683 (1,47); 1,7635 (1,47); 1,7459 (1,26); 1,7348 (0,57); 1,7292 (0,56); 1,7258 (0,53); 1,712 (0,36); 1,1747 (16); 1,1582 (15,98); -

2-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H 0,0002 (5,09)

Verbindung Nr.2-62, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1498 (1,56); 8,1366 (2,79); 8,1233 (1,56); 7,8286 (8,44); 7,8154 (8,79); 7,4104 (4,01); 7,406 (7,09); 7,4014 (4,27); 7,3289 (16); 7,3244 (14,18); 7,1458 (8,75); 7,1326 (8,5); 3,3373 (40,62); 3,278 (2,6); 3,2612 (6,29); 3,2459 (6,37); 3,2291 (2,75); 2,6748 (4,59); 2,6562 (7,63); 2,6371 (4,76); 2,5459 (24,64); 2,5109 (16,05); 2,5065 (20,86); 2,5021 (15,75); 2,0796 (0,8); 1,8661 (1,37); 1,8481 (4,23); 1,8296

2-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H (5,7); 1,8114(4,02); 1,7937 (1,19); -0,0002 (4,86)

Verbindung Nr.2-63, Solvent: [DMSO], Spektrometer: 399.95MHz

2-63 2,6-dimethyl- CH2 CH2 CH(CH3) H 8,032 (0,6); 8,012 (0,61); 7,827 (1,81); 7,8139 (1,91); 7,1533 (1,91); 7,1402 (1,89);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

phenyl 6,9544 (7,38); 4,0757 (0,36); 4,0586 (0,44); 4,0408 (0,37); 3,4371 (0,33); 3,4069

(0,64); 3,3327 (1566,67); 3,2526 (0,79); 2,6753 (2,51); 2,6709 (3,44); 2,6667 (2,56); 2,6427 (0,6); 2,632 (0,64); 2,6164 (0,66); 2,6043 (0,67); 2,5877 (0,81); 2,5412 (8,13); 2,524 (10,07); 2,5063 (342,36); 2,5018 (450,83); 2,4974 (340,1); 2,333 (2,2); 2,3286 (2,98); 2,3242 (2,23); 2,2892 (0,34); 2,2684 (16); 2,074 (1,53); 1,6333 (0,42); 1,6129 (0,75); 1,5953 (0,83); 1,5745 (0,42); 1,2272 (3,92); 1,2105 (3,81); -0,0002 (14,36)

Verbindung Nr.2-64, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0067 (2,51); 7,9859 (2,51); 7,8239 (7,71); 7,8108 (7,96); 7,6441 (6,59); 7,6238 (8,04); 7,452 (7,31); 7,432 (6,19); 7,147 (8,01); 7,1339 (7,7); 3,9855 (0,56); 3,9649 (1,23); 3,95 (1,59); 3,9344 (1,3); 3,9139 (0,6); 3,3391 (108,58); 3,1416 (0,54); 3,1188 (0,5); 2,7982 (0,34); 2,7829 (0,51); 2,7749 (0,48); 2,7634 (1,56); 2,7433 (2,75); 2,7255 (3,38); 2,705 (1,59); 2,6909 (0,61); 2,67 (0,54); 2,5443 (31,93); 2,5273 (0,69); 2,5136 (12,32); 2,5094 (24,5); 2,5049 (32,71); 2,5005 (24,74); 2,4964 (12,74); 2,077 (0,63); 1,923 (0,4); 1,9073 (0,5); 1,9008 (0,81); 1,8879 (1,13); 1,8787 (0,77); 1,8739 (1,09); 1,8668 (1,76); 1,8519 (1,5); 1,8453 (1,15);

4-trifluormethyl- 1,8308 (1,44); 1,815 (1,37); 1,8081 (1,1); 1,8008 (1,39); 1,7948 (1,37); 1,7777

(1,19); 1,7672 (0,59); 1,761 (0,57); 1,7439 (0,37); 1,1872 (15,95); 1,1707 (16); -

2-64 phenyl CH2 CH2 CH(CH3) H 0,0002 (5,54)

Verbindung Nr. 2-65, Solvent: [DMSO], Spektrometer: 399.95MHz-8,0047 (2,66); 7,984 (2,69); 7,8266 (7,82); 7,8135 (8,07); 7,4572 (6,76); 7,4506 (12,88); 7,4292 (8,59); 7,312 (4,56); 7,3056 (4,19); 7,2907 (3,38); 7,2842 (3,13); 7,1485 (8,14); 7,1353 (7,92); 4,03 (0,63); 4,0109 (1,35); 3,9946 (1,87); 3,9783 (1,44); 3,9592 (0,66); 3,337 (33,58); 2,8178 (0,53); 2,8018 (0,69); 2,7949 (0,75); 2,7834 (1,75); 2,7681 (1,8); 2,7601 (2,24); 2,7527 (1,93); 2,7443 (1,99); 2,7351 (2,36); 2,7294 (1,88); 2,7123 (1,81); 2,7002 (0,8); 2,6959 (0,69); 2,6778 (0,67); 2,5459 (21,32); 2,5291 (0,42); 2,5111 (14,05); 2,5066 (18,48); 2,5022 (13,85); 2,0797 (1,06); 1,8417 (0,35); 1,8237 (1,25); 1,8093 (2); 1,8 (2,44); 1,7954 (2,45); 1,7871 (2,82); 1,7808 (2,77); 1,7729 (2,03); 1,7659 (1,51); 1,756 (1,33); 1,7399 (0,34);

2-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H 1,2061 (16); 1,1895 (15,93); -0,0002 (5,28)

2-66 4-phenoxy-phenyl CH2 CH2 CH2 H

2-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

2-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

2-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

Verbindung Nr. 2-70, Solvent: [DMSO], Spektrometer: 399.95MHz-8,3169 (0,83); 7,9735 (2,48); 7,9528 (2,5); 7,8211 (8,06); 7,8079 (8,36); 7,3656 (3,83); 7,3272 (2,7); 7,3233 (3,07); 7,3086 (3,46); 7,3047 (3,93); 7,2864 (1,41); 7,2821 (1,36); 7,2671 (3,42); 7,2628 (3,05); 7,2477 (2,97); 7,2433 (2,47); 7,1952 (2,86); 7,1925 (3,33); 7,1796 (8,97); 7,174 (5,06); 7,1526 (5,06); 7,1455 (9,38); 7,1323 (11,35); 6,9939 (3,94); 3,9968 (0,59); 3,9773 (1,28); 3,9613 (1,77); 3,9452 (1,36); 3,9256 (0,61); 3,3351 (80,76); 3,3113 (0,69); 2,7451 (0,57); 2,7303 (0,72); 2,7209 (0,8); 2,7108 (1,67); 2,6961 (1,56); 2,6865 (1,8); 2,6709 (2,03); 2,6504 (1,83);

2-difluormethoxy- 2,6427 (1,62); 2,6268 (1,64); 2,6161 (0,79); 2,6086 (0,76); 2,5924 (0,67); 2,5423

2-70 phenyl CH2 CH2 CH(CH3) H (33,94); 2,5255 (0,69); 2,5118 (11,77); 2,5075 (23,24); 2,503 (30,78); 2,4985

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(23,06); 2,4942 (11,62); 2,0754 (1,11); 1,8303 (0,44); 1,8219 (0,49); 1,8114 (1,2); 1,7969 (1,17); 1,7877 (1,66); 1,7771 (1,65); 1,7731 (1,52); 1,7665 (2,34); 1,7505 (1,84); 1,7409 (1,62); 1,7309 (0,81); 1,7252 (1,09); 1,7164 (0,42); 1,7077 (0,54); 1,1919 (16); 1,1753 (15,87); -0,0002 (6,33)

2-71 4-methoxy-phenyl CH2 CH2 CH2 H

Verbindung Nr. 2-72, Solvent: [DMSO], Spektrometer: 399.95MHz-7,9867 (2,32); 7,9661 (2,36); 7,8197 (7,69); 7,8066 (8,01); 7,3355 (7,83); 7,3309 (2,86); 7,3192 (3,58); 7,3145 (12,43); 7,3085 (1,76); 7,2423 (10,76); 7,2214 (6,89); 7,1448 (8,08); 7,1316 (7,83); 3,9585 (0,56); 3,9379 (1,2); 3,9232 (1,56); 3,9074 (1,25); 3,887 (0,57); 3,3692 (0,6); 3,3315 (338,35); 3,2986 (0,6); 2,7118 (0,33); 2,6914 (0,43); 2,6761 (1,11); 2,671 (1,14); 2,6673 (1,05); 2,6571 (1,73); 2,6419 (2); 2,6349 (3,2); 2,6186 (3,68); 2,5962 (1,77); 2,5832 (0,68); 2,5788 (0,73); 2,5608 (0,77); 2,5415 (69,61); 2,5246 (2,52); 2,511 (43,01); 2,5067 (84,57); 2,5022 (111,66); 2,4977 (83,25); 2,4934 (41,77); 2,3334 (0,52); 2,3289 (0,73); 2,3245 (0,53); 2,0746 (0,52); 1,8747 (0,4); 1,8591 (0,51); 1,8526 (0,8); 1,8401 (1,14); 1,8261 (1,03); 1,8186 (1,69); 1,804 (1,42); 1,7971 (1,05); 1,7804 (1,16); 1,7621 (1,26); 1,7553 (0,99); 1,7478 (1,32); 1,7418 (1,29); 1,7245 (1,12); 1,7141 (0,56); 1,7078 (0,57); 1,6909 (0,37); 1,1707 (16); 1,1542 (15,9); 0,0079 (0,47); -0,0002

2-72 4-chlor-phenyl CH2 CH2 CH(CH3) H (12,91); -0,0085 (0,49)

Verbindung Nr.2-73, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8783 (1,86); 7,8552 (1,89); 7,8267 (4,97); 7,8135 (5,15); 7,3278 (5,08); 7,3234 (1,93); 7,3068 (8,36); 7,3012 (1,31); 7,2428 (7,42); 7,2218 (4,62); 7,1557 (5,24); 7,1426 (5,07); 3,8106 (0,37); 3,7973 (0,6); 3,7872 (1,02); 3,7746 (1,18); 3,7628 (1,01); 3,7518 (0,64); 3,7389 (0,38); 3,3356 (51,87); 2,691 (0,46); 2,6766 (0,69); 2,6686 (0,67); 2,6559 (1,09); 2,6415 (0,96); 2,6351 (0,92); 2,6197 (0,8); 2,5656 (0,8); 2,5434 (16,86); 2,5252 (1,33); 2,5086 (15,1); 2,5041 (19,29); 2,4997 (14,5); 2,4957 (7,55); 2,0766 (0,66); 1,8277 (0,33); 1,8115 (0,99); 1,7946 (1,75); 1,7793 (2,43); 1,7614 (2,44); 1,7442 (1,76); 1,7209 (0,66); 0,8907 (16); 0,8737 (15,72); -

2-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H 0,0002 (3,83)

Verbindung Nr. 2-74, Solvent: [DMSO], Spektrometer: 399.95MHz-8,1571 (2,3); 8,1445 (3,97); 8,1314 (2,32); 7,8233 (13,46); 7,8101 (14); 7,7932 (0,52); 7,7801 (0,41); 7,2736 (6,93); 7,2686 (3,51); 7,2592 (8,85); 7,2522 (10); 7,238 (8,69); 7,1744 (0,47); 7,1614 (0,51); 7,1437 (14,16); 7,1306 (14,46); 7,1211 (10,44); 7,1159 (3,53); 7,0987 (16); 7,0931 (4,15); 7,0813 (3,4); 7,0766 (7,52); 7,069 (0,99); 3,3804 (0,36); 3,3684 (0,65); 3,3369 (163,66); 3,298 (0,48); 3,2807 (4,34); 3,2637 (9,62); 3,2486 (9,89); 3,2314 (4,51); 2,6774 (0,37); 2,6727 (0,48); 2,6685 (0,4); 2,6413 (6,93); 2,6225 (11,06); 2,6031 (7,46); 2,5431 (57,57); 2,5261 (1,62); 2,5122 (25,08); 2,5082 (46,38); 2,5038 (58,81); 2,4993 (43,77); 2,3305 (0,39); 2,0761 (0,8); 1,842 (2,3); 1,8236 (6,48); 1,8051 (8,74); 1,7868 (6,2); 1,7686

2-74 4-fluor-phenyl CH2 CH2 CH2 H (2,03); -0,0002 (7,35)

Verbindung Nr. 2-75, Solvent: [DMSO], Spektrometer: 399.95MHz-7,913 (2,57); 7,8908 (2,61); 7,8173 (7,32); 7,8042 (7,58); 7,3287 (7,24); 7,3242 (2,78); 7,3123 (3,44); 7,3077 (11,59); 7,3019 (1,79); 7,2372 (10,16); 7,2162 (6,51); 7,1456 (7,76); 7,1325 (7,5); 3,934 (0,76); 3,9158 (1,37); 3,8985 (1,39); 3,8803 (0,8);

2-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H 3,3318 (66,92); 2,687 (0,51); 2,6681 (1,18); 2,6522 (1,5); 2,6336 (2,24); 2,6145

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(2,4); 2,5944 (2,63); 2,574 (1,47); 2,5596 (1,23); 2,5427 (30,42); 2,5259 (0,81); 2,5122 (12,8); 2,5079 (25,23); 2,5034 (33,46); 2,4988 (25,21); 2,4945 (12,78); 2,0761 (0,7); 1,7893 (1,87); 1,7697 (3,93); 1,7521 (4,42); 1,7329 (1,74); 1,5174 (0,93); 1,5077 (1,11); 1,5022 (1,44); 1,4936 (2,52); 1,4751 (3,44); 1,4574 (2); 1,3922 (0,39); 1,3749 (0,68); 1,359 (1,34); 1,3408 (1,88); 1,3332 (1,34); 1,3234 (1,73); 1,3153 (1,85); 1,3097 (1,31); 1,2973 (1,52); 1,2927 (1,32); 1,2815 (0,85); 1,2751 (0,93); 1,2636 (0,48); 1,2594 (0,51); 0,8802 (7,91); 0,862 (16); 0,8437 (6,75); 0,0079 (0,5); -0,0002 (13,95); -0,0084 (0,56)

Verbindung Nr. 2-76, Solvent: [DMSO], Spektrometer: 399.95MHz7,8382 (0,75); 7,8328 (2,07); 7,8196 (2,18); 7,8147 (0,8); 7,3251 (1,73); 7,3205 (0,67); 7,304 (3,07); 7,2498 (2,74); 7,2287 (1,61); 7,1615 (1,96); 7,1484 (1,9); 3,7538 (0,64); 3,7297 (0,33); 3,3375 (20,94); 2,6423 (0,42); 2,5436 (5,53); 2,5129 (2,71); 2,5088 (5,29); 2,5043 (6,98); 2,4998 (5,29); 2,4957 (2,88); 2,4775 (0,4); 2,4722

2-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H (0,39); 2,4543 (0,34); 1,8132 (0,35); 0,8896 (16); -0,0002 (1,78)

Verbindung Nr.2-77, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3164 (1,67); 8,2073 (2,43); 8,1943 (4,32); 8,1807 (2,43); 7,825 (15,3); 7,8118 (15,85); 7,7946 (0,56); 7,7814 (0,47); 7,4225 (6,56); 7,4191 (6,47); 7,4033 (8,42); 7,3997 (8,42); 7,3877 (5,38); 7,3833 (5,76); 7,369 (7,45); 7,3647 (7,89); 7,3035 (3,37); 7,3001 (3,73); 7,2852 (8,28); 7,2816 (7,74); 7,2668 (5,54); 7,263 (4,67); 7,2539 (6,07); 7,2491 (6,17); 7,2348 (6,74); 7,2303 (6,52); 7,2161 (2,64); 7,2116 (2,32); 7,1756 (0,5); 7,1625 (0,55); 7,1452 (16); 7,132 (15,45); 7,1237 (0,48); 3,3931 (0,48); 3,3741 (1,12); 3,341 (242,72); 3,3129 (11,63); 3,2976 (11); 3,2806 (4,82); 2,77 (8,21); 2,7511 (10,28); 2,7311 (8,72); 2,7137 (0,41); 2,6775 (0,46); 2,6731 (0,59); 2,5434 (63,34); 2,5263 (1,92); 2,5128 (26,19); 2,5086 (50,46); 2,5041 (66,35); 2,4996 (49,74); 2,4953 (25,17); 2,3309 (0,42); 2,0761 (1,44); 1,8538 (2,51); 1,8356 (6,53); 1,8167 (8,34); 1,798 (6,21); 1,78 (2,14); 0,0079 (0,4);

2-77 2-chlor-phenyl CH2 CH2 CH2 H -0,0002 (9,67); -0,0085 (0,36)

Verbindung Nr.2-78, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1901 (2,91); 8,1777 (5); 8,1657 (3,06); 7,8261 (12,85); 7,825 (12,4); 7,8129 (13,52); 7,8119 (13,05); 7,7953 (0,6); 7,7822 (0,44); 7,3203 (8,78); 7,3076 (9,55); 7,1752 (0,42); 7,1621 (0,47); 7,1455 (13,66); 7,1445 (13,08); 7,1323 (13,35); 7,1313 (12,76); 6,9515 (6,41); 6,9427 (8,97); 6,9391 (7,19); 6,9302 (8,23); 6,8872 (10,26); 6,8791 (8,24); 3,3314 (106,28); 3,3073 (13,58); 3,2915 (13,3); 3,2749 (5,96); 2,872 (9,41); 2,853 (16); 2,8339 (10,05); 2,6709 (0,58); 2,5417 (2,78); 2,5407 (2,62); 2,502 (75,43); 2,4981 (60,55); 2,3286 (0,49); 1,9003 (2,93); 1,8821

2-78 2-thienyl CH2 CH2 CH2 H (9,04); 1,8636 (12,17); 1,8453 (8,71); 1,8273 (2,7); -0,0002 (0,7)

[DMSO], Spektrometer: 399,95MHz

7,9988 (3,15); 7,9778 (3,21); 7,7997 (7,73); 7,7866 (8,07); 7,7711 (0,4); 7,3519 (0,8); 7,3316 (2,07); 7,3143 (3,69); 7,2939 (2,51); 7,2767 (1,05); 7,1338 (0,37); 7,1153 (8,38); 7,1022 (8,12); 7,0815 (0,95); 7,0692 (5,57); 7,0498 (8,8); 7,03 (4,77); 7,0178 (0,82); 4,2991 (0,8); 4,2811 (1,87); 4,263 (2,47); 4,245 (1,98); 4,2275 (0,89); 3,3347 (26,57); 2,9301 (0,44); 2,8921 (5,54); 2,876 (6,4); 2,8396 (0,39); 2,6724 (0,5); 2,5073 (57,25); 2,5032 (75,74); 2,4992 (61,74); 2,33 (0,51); 1,336 (0,44); 1,2491 (0,44); 1,2325 (0,34); 1,1897 (15,85); 1,173 (16); 0,0078

2-79 2,6-difluor-phenyl CH2 CH(CH3) H (1,35); -0,0002 (27,44)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr.2-80, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3205 (0,33); 7,7755 (5,45); 7,7655 (5,62); 7,3258 (9,27); 7,1826 (0,48); 7,0807 (9,65); 7,0682 (9,73); 4,0378 (0,69); 4,02 (0,69); 3,6776 (3,09); 3,5874 (0,71); 3,4941 (2,32); 3,3355 (59,17); 3,0207 (4,31); 2,8772 (10,16); 2,6765 (0,74); 2,6724 (0,97); 2,6681 (0,75); 2,5077 (99,47); 2,5033 (128,84); 2,4989 (96,92); 2,3344 (0,65); 2,3302 (0,86); 2,3258 (0,64); 2,08 (0,37); 2,0357 (0,37); 1,9901 (2,95); 1,397 (16); 1,3364 (0,65); 1,2491 (0,76); 1,1929 (0,8); 1,1751 (1,54); 1,1573

2-80 4-chlor-phenyl CH2 CH2 CH3 (0,76); 0,1459 (0,32); 0,0079 (3,23); -0,0002 (69,14); -0,008 (3,38)

Verbindung Nr.2-81, Solvent: [DMSO], Spektrometer: 399.95MHz

7,7744 (5,47); 7,7613 (5,66); 7,3331 (4,15); 7,0949 (4,31); 7,0821 (4,33); 3,6253 (1,16); 3,4958 (1,18); 3,4703 (1,16); 3,461 (1,16); 3,3349 (23,98); 3,1896 (1,01); 2,8679 (1,6); 2,6723 (0,39); 2,5076 (42,89); 2,5032 (56,18); 2,4988 (43,26); 2,3301 (0,37); 1,99 (0,39); 1,3969 (16); 1,1925 (0,58); 1,1747 (1,07); 1,1563 (1,39);

2-81 4-chlor-phenyl CH2 CH2 CH2CH3 1,1382 (1,45); 1,0351 (1,92); 0,0076 (1,23); -0,0002 (27,9); -0,0081 (1,7)

Verbindung Nr.2-82, Solvent: [DMSO], Spektrometer: 399.95MHz

7,7789 (1,34); 7,768 (1,36); 7,5866 (0,34); 7,4841 (0,42); 7,3806 (1,21); 7,3627 (1,15); 7,3 (0,4); 7,0753 (1,27); 3,7028 (0,63); 3,552 (0,68); 3,3362 (10,02); 3,0647 (1,36); 3,0082 (1,02); 2,908 (1,77); 2,5125 (10,77); 2,5084 (20,65); 2,5039 (26,86); 2,4995 (20,26); 2,4955 (10,59); 1,9906 (1,01); 1,3968 (16); 1,1755 (0,52); 0,0079

2-82 2,4-dichlor-phenyl CH2 CH2 CH3 (0,69); -0,0002 (15,22); -0,0082 (0,77)

Verbindung Nr.2-83, Solvent: [DMSO], Spektrometer: 399.95MHz

7,9847 (2,32); 7,964 (2,34); 7,8206 (7,99); 7,8075 (8,3); 7,2518 (3,78); 7,2468 (1,98); 7,2375 (4,78); 7,2304 (5,75); 7,2216 (2,28); 7,2162 (4,99); 7,146 (8,38); 7,1329 (8,13); 7,1185 (0,76); 7,111 (5,83); 7,1059 (1,95); 7,0944 (2,19); 7,0887 (9,22); 7,083 (2,33); 7,0715 (1,62); 7,0665 (4,36); 7,059 (0,52); 3,967 (0,57); 3,9466 (1,26); 3,9312 (1,62); 3,9159 (1,29); 3,8953 (0,59); 3,3367 (86,22); 2,6906 (0,41); 2,6753 (0,71); 2,6674 (0,66); 2,6556 (1,69); 2,6407 (1,87); 2,6329 (3,28); 2,6164 (3,4); 2,5935 (1,7); 2,5808 (0,58); 2,5764 (0,66); 2,5589 (0,64); 2,5432 (28,9); 2,5262 (0,6); 2,5125 (10,86); 2,5083 (21,49); 2,5038 (28,59); 2,4993 (21,7); 2,4951 (11,17); 2,0762 (0,68); 1,8757 (0,44); 1,8603 (0,54); 1,8534 (0,84); 1,841 (1,21); 1,827 (1,09); 1,8194 (1,73); 1,805 (1,45); 1,7979 (1,09); 1,7825 (0,88); 1,777 (0,95); 1,7601 (1,33); 1,7529 (1,04); 1,7459 (1,36); 1,7394 (1,35); 1,7225 (1,17); 1,7123 (0,59); 1,7057 (0,6); 1,7029 (0,57); 1,6888 (0,39); 1,1742 (16);

2-83 4-fluor-phenyl CH2 CH2 CH(CH3) H 1,1577 (15,87); 0,0079 (0,37); -0,0002 (10,23); -0,0083 (0,43)

Verbindung Nr.2-84, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4971 (0,48); 8,4816 (0,94); 8,466 (0,47); 7,8552 (2,26); 7,842 (2,34); 7,5789 (16); 7,1512 (2,37); 7,138 (2,3); 6,5757 (0,41); 4,0669 (0,61); 4,0511 (0,63); 4,0313 (1,35); 4,0155 (1,31); 3,9954 (0,69); 3,9796 (0,65); 3,3486 (47,96); 2,9452

2-84 4-chlor-phenyl CF2 CH2 H (2,52); 2,5086 (10,05); 2,5044 (13,29); 2,5001 (10,38)

Verbindung Nr.2-85, Solvent: [DMSO], Spektrometer: 601.6MHz

19,9671 (0,42); 8,3173 (2,02); 7,7769 (7,1); 7,3518 (10,48); 7,0829 (14,02); 6,9538 (14,91); 6,9485 (14,76); 6,7584 (4,17); 5,4222 (0,41); 4,6286 (0,4); 4,6186 (0,42); 4,2709 (0,36); 4,0466 (0,39); 4,0346 (1,08); 4,0227 (1,07); 4,0108 (0,34); 3,8995 (0,35); 3,6964 (8,82); 3,5095 (7,68); 3,3745 (0,46); 3,3655 (0,42); 3,327 (604,31); 3,2896 (0,8); 3,2808 (0,43); 3,2182 (0,4); 3,1085 (12,03); 3,0584 (12,67); 3,0313

2-85 2-thienyl CH2 CH2 CH3 (15,74); 2,8975 (16); 2,7797 (0,49); 2,6166 (4,14); 2,6136 (5,62); 2,6106 (4,1);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr.2-90, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1254 (1,64); 8,1114(2,96); 8,098 (1,58); 7,8191 (11,94); 7,8059 (12,35); 7,7851 (0,39); 7,7721 (0,4); 7,5 (1,64); 7,4936 (13,56); 7,4891 (4,57); 7,4774 (4,83); 7,4728 (16); 7,4665 (1,88); 7,232 (2,14); 7,2256 (13,05); 7,2047 (11,17); 7,1611 (0,44); 7,148 (0,44); 7,1311 (12,58); 7,118 (12,11); 4,0378 (0,35); 4,02 (0,35); 3,4987 (3,04); 3,4814 (6,52); 3,4664 (6,37); 3,4484 (3,36); 3,3228 (89,09); 2,832 (5,84); 2,8139 (10,28); 2,7961 (5,26); 2,6753 (0,74); 2,6707 (1,02); 2,6663 (0,74); 2,662 (0,36); 2,524 (3,23); 2,5106 (57,68); 2,5062 (114,89); 2,5017 (150,1); 2,4971 (107,93); 2,4926 (51,79); 2,333 (0,68); 2,3284 (0,95); 2,3238 (0,69); 2,3193 (0,33); 1,9888 (1,56); 1,3355 (0,36); 1,2492 (0,46); 1,1925 (0,42); 1,1747 (0,81); 1,1569

2-90 4-brom-phenyl CH2 CH2 H (0,4); 0,0079 (2,31); -0,0002 (63,05); -0,0085 (2,15)

Verbindung Nr.2-91, Solvent: [DMSO], Spektrometer: 399.95MHz

7,7942 (2); 7,7937 (1,96); 7,781 (2,13); 7,479 (0,83); 7,3998 (1,54); 7,3369 (2,48); 7,3161 (3,41); 7,1964 (3,15); 7,1756 (2,48); 7,116 (2,01); 7,103 (2); 5,3272 (0,4); 3,3499 (30,78); 3,3455 (30,99); 3,3393 (29,64); 3,3302 (12,71); 3,0776 (5,05); 2,5065 (13,57); 2,5026 (18); 2,4987 (15,17); 1,3346 (0,5); 1,3178 (16); -0,0002

2-91 4-chlor-phenyl CH2 C(CH3)2 H (3,62); -0,0012 (3,61)

Verbindung Nr.2-92, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8127 (2,03); 7,8119 (1,97); 7,7996 (2,18); 7,7987 (2,09); 7,5885 (1,94); 7,5833 (2,15); 7,5469 (1,81); 7,366 (0,84); 7,361 (0,84); 7,3452 (1,45); 7,3402 (1,51); 7,2883 (2,5); 7,2674 (1,51); 7,1329 (2,23); 7,1198 (2,2); 4,0387 (0,54); 4,0209 (0,55); 3,3322 (20,83); 3,269 (5,62); 2,5073 (7,09); 2,5032 (9,69); 2,499 (7,85); 1,9896 (2,27); 1,35 (16); 1,1938 (0,62); 1,1929 (0,61); 1,176 (1,2); 1,1751 (1,15);

2-92 2,4-dichlor-phenyl CH2 C(CH3)2 H 1,1582 (0,6); -0,0002 (2,55); -0,0013 (2,37)

Verbindung Nr.2-93, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2642 (1,96); 8,2498 (3,72); 8,2357 (1,92); 7,8279 (15,21); 7,8147 (15,83); 7,7488 (6,83); 7,7434 (10,04); 7,7323 (4,84); 7,7267 (2,66); 7,7115 (5,13); 7,7061 (3,97); 7,5482 (6,98); 7,5275 (5,7); 7,1385 (16); 7,1254 (15,5); 3,5401 (2,97); 3,5233 (6,91); 3,5071 (6,93); 3,4898 (3,3); 3,3246 (34,18); 3,3123 (0,54); 3,304 (4,59); 3,2957 (0,38); 3,2862 (3,62); 3,0151 (4,29); 2,9976 (7,73); 2,98 (3,73); 2,6964 (14,95); 2,6769 (0,42); 2,6724 (0,55); 2,6678 (0,39); 2,5257 (1,76); 2,521 (2,72); 2,5124 (30,57); 2,5079 (60,58); 2,5033 (79,28); 2,4987 (56,52); 2,4941 (26,25); 2,3346 (0,37); 2,3301 (0,52); 2,3253 (0,35); 2,1981 (1,63); 2,1781 (3,1); 2,1576 (2,19); 1,9396 (0,85); 1,9214 (2,12); 1,9182 (1,5); 1,9126 (0,39); 1,9029 (2,26);

2-(trifluormethyl)- 1,8923 (0,35); 1,883 (1,91); 1,8798 (0,87); 1,864 (0,57); 1,3365 (2,02); 1,2587

(0,39); 1,2496 (2,47); 1,2334 (0,42); 1,1881 (0,78); 0,008 (0,87); -0,0002 (25,1); -

2-93 4-chlorphenyl CH2 CH2 H 0,0085 (0,69)

Verbindung Nr.2-94, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0435 (2,25); 8,0237 (2,28); 7,8444 (8,97); 7,8313 (9,27); 7,5738 (7,85); 7,5674 (8,35); 7,386 (3,73); 7,3795 (3,44); 7,3638 (5); 7,3574 (4,75); 7,2389 (7,4); 7,2166 (5,53); 7,1533 (9,63); 7,1401 (9,23); 4,3985 (0,56); 4,3832 (1,22); 4,3662 (1,53); 4,3476 (1,31); 4,332 (0,66); 4,1699 (1,65); 4,1548 (1,49); 4,1455 (3,5); 4,1304 (3,06); 4,1114 (3,5); 4,0974 (3,32); 4,087 (1,78); 4,073 (1,45); 3,3802 (0,32); 3,3735 (0,47); 3,3343 (380,72); 3,2974 (0,41); 2,6762 (0,59); 2,6716 (0,8); 2,6672 (0,57); 2,5419 (14,79); 2,525 (2,2); 2,5202 (3,54); 2,5117 (46,3); 2,5072 (93,4);

2-94 2,4-dichlor-phenyl 0 CH2 CH(CH3) H 2,5026 (123); 2,498 (88,09); 2,4934 (41,35); 2,3339 (0,57); 2,3293 (0,81); 2,3247

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(0,58); 1,2919 (16); 1,2749 (15,85); 0,008 (0,75); -0,0002 (23,38); -0,0086 (0,66)

Verbindung Nr.2-96, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1037 (2,62); 8,0836 (2,64); 7,8406 (8,35); 7,8274 (8,63); 7,6262 (7,86); 7,6205 (8,15); 7,5734 (5,55); 7,5519 (7,26); 7,4258 (4,73); 7,4201 (4,43); 7,4043 (3,64); 7,3986 (3,44); 7,1488 (8,79); 7,1356 (8,49); 4,1854 (0,67); 4,1681 (1,49); 4,1503 (1,96); 4,1328 (1,53); 4,1153 (0,7); 3,3486 (0,62); 3,3298 (110,3); 3,3052 (2,03); 3,2872 (1,82); 3,272 (3,23); 3,2538 (3,07); 3,1986 (3,29); 3,183 (3,35); 3,1653 (2); 3,1496 (1,83); 2,672 (0,36); 2,5422 (20,2); 2,5253 (1,27); 2,5119 (21,46); 2,5075 (42); 2,5029 (54,69); 2,4983 (39,66); 2,4939 (19,17); 2,3296 (0,34); 1,3058 (16);

2-95 4-chlor-phenyl 0 CH2 CH(CH3) H 1,2892 (15,83); -0,0002 (6,66)

Verbindung Nr.2-96, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1037 (2,62); 8,0836 (2,64); 7,8406 (8,35); 7,8274 (8,63); 7,6262 (7,86); 7,6205 (8,15); 7,5734 (5,55); 7,5519 (7,26); 7,4258 (4,73); 7,4201 (4,43); 7,4043 (3,64); 7,3986 (3,44); 7,1488 (8,79); 7,1356 (8,49); 4,1854 (0,67); 4,1681 (1,49); 4,1503 (1,96); 4,1328 (1,53); 4,1153 (0,7); 3,3486 (0,62); 3,3298 (110,3); 3,3052 (2,03); 3,2872 (1,82); 3,272 (3,23); 3,2538 (3,07); 3,1986 (3,29); 3,183 (3,35); 3,1653 (2); 3,1496 (1,83); 2,672 (0,36); 2,5422 (20,2); 2,5253 (1,27); 2,5119 (21,46); 2,5075 (42); 2,5029 (54,69); 2,4983 (39,66); 2,4939 (19,17); 2,3296 (0,34); 1,3058 (16);

2-96 2,4-dichlor-phenyl s CH2 CH(CH3) H 1,2892 (15,83); -0,0002 (6,66)

Verbindung Nr.2-97, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0313 (2,28); 8,0111 (2,27); 7,8351 (7,34); 7,8276 (0,77); 7,822 (7,61); 7,4468 (0,36); 7,4416 (0,39); 7,4184 (5,41); 7,4131 (2,2); 7,4022 (3,25); 7,3966 (13,89); 7,3911 (2,42); 7,3736 (2,38); 7,3681 (14,46); 7,3625 (3,43); 7,3516 (2,29); 7,3463 (5,62); 7,3404 (0,88); 7,3333 (0,67); 7,3158 (0,37); 7,1509 (0,57); 7,1443 (7,83); 7,1379 (0,74); 7,1311 (7,56); 4,1367 (0,71); 4,1196 (1,54); 4,1015 (1,92); 4,0835 (1,56); 4,0664 (0,72); 3,3511 (0,6); 3,3303 (126,34); 3,2924 (0,34); 3,2547 (2,01); 3,2369 (1,94); 3,2209 (3,27); 3,2031 (3,13); 3,1345 (3,43); 3,1187 (3,44); 3,1008 (2,14); 3,0849 (1,99); 2,6713 (0,39); 2,5417 (12,91); 2,5244 (1,23); 2,5112 (23,65); 2,5069 (46,72); 2,5024 (61,31); 2,4978 (44,84); 2,4935 (22,01); 2,3291 (0,39); 1,3123 (0,69); 1,2957 (0,74); 1,2793 (1,26); 1,2672 (16); 1,2505 (15,69); -0,0002

2-97 4-chlor-phenyl s CH2 CH(CH3) H (6,61)

Verbindung Nr.2-98, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1784 (0,63); 8,1644 (1,19); 8,1511 (0,64); 7,832 (3,85); 7,8188 (3,97); 7,1823 (0,46); 7,1735 (4,39); 7,1681 (1,47); 7,1561 (1,75); 7,1508 (4,9); 7,1399 (4,35); 7,1267 (3,97); 6,78 (0,54); 6,7713 (4,48); 6,766 (1,59); 6,7536 (1,52); 6,7485 (4,03); 6,7396 (0,46); 3,4961 (0,89); 3,4802 (2,47); 3,4646 (2,25); 3,4296 (1,28); 3,4143 (2,21); 3,3992 (1,71); 3,3837 (0,55); 3,3285 (37,94); 2,9175 (16); 2,5417 (14,97); 2,5245 (0,68); 2,5111 (10,02); 2,5068 (18,95); 2,5023 (24,27); 2,4977

2-98 4-chlor-phenyl N(CH3) CH2 CH2 H (17,83); 2,4934 (8,9); -0,0002 (3,85)

3-chlor-4-

(trifluormethyl)- Verbindung Nr.2-99, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8169 (0,34); 7,8037 (0,35); 7,1258 (0,35); 7,1126 (0,34); 5,7548 (16); 3,3218

2-99 phenyl CH2 CH2 H (3,21); 2,5111 (2,65); 2,5067 (5,19); 2,5021 (6,78); 2,4975 (4,91); 2,4931 (2,38)

4-chlor-3- Verbindung Nr.2-100, Solvent: [DMSO], Spektrometer: 399.95MHz

2-100 (trifluormethyl)- CH2 CH2 H 8,1546 (1,81); 8,1411 (3,36); 8,1274(1,79); 7,8227(15,02); 7,8095 (15,47); 7,7309

- p eny 2,3267 (0,42); 1,234 (0,34); -0,0002 (0,46)

Tabelle 3

Verbindungen der Formel 1-3

Tabelle 4

Verbindungen der Formel 1-4

Physikalische Daten: ^] H-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

4-1 3 -methyl-2-thienyl CH2 CH2 - H WO-A 2006/108791

4-2 3-chlor-2-thienyl CH2 CH2 - H WO-A 2006/108791

4-3 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101976

4-4 4-chlor-phenyl CH2 CH2 - H

4-5 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

4-6 4-chlor-phenyl CH(OCH3) CH(CH3) - H

4-7 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

Verbindung Nr. 4-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1978 (1 ,28); 8,1836 (2,49); 8,1694 (1 ,27); 7,6731 (9,43); 7,6604 (9,81 ); 7,3745 (0,77); 7,3688 (6,87); 7,3638 (2,5); 7,3527 (3,53); 7,3475 (15,13); 7,3419 (2,2); 7,3161 (2,24); 7,3108 (13,08); 7,3056 (3,36); 7,2943 (2,33); 7,2894 (6,14); 7,1873 (10,07); 7,1745 (9,59); 3,4045 (0,36); 3,3904 (3); 3,3871 (2,85); 3,3719 (5,93); 3,3549 (4,25); 3,3334 (135,39); 3,0838 (1 ,26); 3,0659 (2,5); 3,0481 (2,41 ); 3,0302 (1 ,12); 2,6716 (0,37); 2,5418 (34,95); 2,5249 (1 ,18); 2,5201 (1 ,86); 2,51 15 (22,13); 2,507 (44,23); 2,5025 (58,05); 2,4979 (41 ,77); 2,4934 (19,73); 2,3293 (0,37); 1 ,2521 (16); 1 ,2346 (15,76); -0,0002

4-8 4-chlor-phenyl CH(CH3) CH2 H (7,44)

Verbindung Nr. 4-9, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2659 (1 ,43); 8,2517 (2,78); 8,2379 (1 ,37);

4-9 2,4-dichlor-phenyl CH(CH3) CH2 H 7,6708 (1 1 ,05); 7,6581 (1 1 ,5); 7,5626 (8,69);

Physikalische Daten: ^] H-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

7,5572 (9,18); 7,4833 (4,64); 7,4621 (8,93); 7,4228 (5,83); 7,4173 (5,36); 7,4017 (2,99); 7,3962 (2,83); 7,1832 (11,46); 7,1705 (10,82); 3,5655 (0,99); 3,5479 (2,21); 3,5307 (2,6); 3,5134 (1,78); 3,5092 (1,48); 3,4948 (1,4); 3,4771 (2,63); 3,4615 (3); 3,4453 (3,26); 3,4306 (2,49); 3,4125 (2,42); 3,3982 (1,06); 3,3796 (0,79); 3,3691 (0,46); 3,3297 (402,14); 3,2983 (0,41); 2,6802 (0,32); 2,6755 (0,69); 2,671 (0,95); 2,6664 (0,69); 2,6618 (0,32); 2,5413 (62,58); 2,5243 (2,87); 2,5195 (4,52); 2,511 (53,88); 2,5065 (108,84); 2,5019 (144,25); 2,4973 (104,06); 2,4927 (49,39); 2,3332 (0,66); 2,3286 (0,93); 2,3241 (0,65); 1,2414(16); 1,2245 (15,82); 0,008 (0,5); -0,0002 (14,84); -0,0085 (0,45)

Verbindung Nr.4-10, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1201 (2,15); 8,0997 (2,16); 7,6702 (8,96); 7,6575 (9,35); 7,3518 (0,84); 7,3459 (7,05); 7,3409 (2,57); 7,3299 (3,49); 7,3247 (14,43); 7,319(2,05); 7,2817(11,16); 7,2767 (3,02); 7,2653 (2,24); 7,2605 (5,63); 7,1814 (9,66); 7,1687 (9,22); 4,1703 (0,59); 4,1538 (1,11); 4,1508 (1,23); 4,1341 (1,75); 4,1176 (1,27); 4,0979 (0,57); 3,3292 (373,27); 2,856 (1,31); 2,8363 (1 ,27); 2,8225 (2,79); 2,8028 (2,75); 2,7753 (2,78); 2,7597 (2,85); 2,7417 (1 ,32); 2,7261 (1,19); 2,6797 (0,41); 2,6754 (0,91); 2,6707 (1,26); 2,6662 (0,89); 2,6616 (0,42); 2,541 (11,06); 2,5242 (4,05); 2,5194 (6,28); 2,5108 (70,9); 2,5063 (142,56); 2,5017 (188,15); 2,497 (134,78); 2,4925 (63,12); 2,3376 (0,41); 2,333 (0,89); 2,3284 (1,22); 2,3238 (0,87); 2,3193 (0,4); 1,1641 (16); 1,1476 (15,9); 0,008 (0,56); -0,0002 (17,08);

4-10 4-chlor-phenyl CH2 CH(CH3) H -0,0086 (0,5)

Verbindung Nr.4-11, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1715 (2,47); 8,1501 (2,54); 7,6701 (9,62); 7,6574 (10,06); 7,5702 (6,37); 7,5652 (6,68); 7,4002 (2,84); 7,3795 (9,34); 7,365 (7,41); 7,3599 (6,8); 7,3444 (2,34); 7,3393 (2,44); 7,1782 (10,2); 7,1655 (9,72); 4,3099 (0,56);

4-11 2,4-dichlor-phenyl CH2 CH(CH3) H 4,2893 (1,25); 4,273 (1,72); 4,2568 (1,19);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

4,2523 (1 ,03); 4,2363 (0,58); 3,3755 (0,44); 3,3304 (524,28); 3,2932 (0,66); 3,28 (0,37); 2,995 (0,76); 2,9591 (0,59); 2,944 (0,89); 2,9247 (4, 16); 2,9161 (4,42); 2,9099 (4,06); 2,8956 (3,55); 2,8819 (0,7); 2,8614 (0,77); 2,6801 (0,53); 2,6755 (1 ,1 1 ); 2,6709 (1 ,52); 2,6663 (1 ,09); 2,6616 (0,5); 2,5412 (72,37); 2,5243 (4,63); 2,5196 (7,08); 2,51 1 (85,7); 2,5064 (173,71 ); 2,5018 (229,57); 2,4972 (164,3); 2,4926 (76,96); 2,3377 (0,52); 2,3332 (1 ,1 1 ); 2,3286 (1 ,52); 2,324 (1 ,08); 2,3195 (0,49); 1 ,2349 (0,56); 1 ,213 (16); 1 , 1963 (15,76); 0,0081 (0,66); -0,0002 (19,69); -0,0085 (0,52)

4-12 4-chlor-phenyl C(CH3)2 CH2 - H

4-13 2,4-dichlor-phenyl C(CH3)2 CH2 - H

4-14 2-chlor-phenyl CH2 CH2 - H

Verbindung Nr. 4-15, Solvent: [DMSO], Spektrometer: 399.95MHz 8,2748 (1 ,63); 8,2609 (3,12); 8,247 (1 ,61 ); 7,6903 (12,52); 7,6776 (12,97); 7,5589 (9,91 ); 7,5486 (0,57); 7,5381 (16); 7,5316 (8,43); 7,2734 (4,72); 7,2683 (4,54); 7,2528 (4,08); 7,2478 (3,97); 7,201 1 (13,09); 7,1884 (12,55); 3,4944 (2,7); 3,4772 (6,94); 3,4626 (7, 1 ); 3,4456 (2,94); 3,3623 (0,52); 3,3573 (0,55); 3,3317 (219, 19); 3,31 (0,65); 2,8624 (5,18); 2,8452 (10,47); 2,8279 (4,63); 2,6761 (0,45); 2,6716 (0,61 ); 2,6669 (0,47); 2,5418 (54,74); 2,5248 (1 ,69); 2,5201 (2,77); 2,51 16 (34,23); 2,5071 (68,94); 2,5025 (90,9); 2,4979 (65,17); 2,4933 (30,68); 2,3337 (0,43); 2,3292 (0,6); 2,3246 (0,41 ); -0,0002 (8,21 )

4-15 3 ,4-dichlor-phenyl CH2 CH2 H

4-16 3,5- dichlor-pheny 1 CH2 CH2 - H

4-17 3-chlor-phenyl CH2 CH2 - H

4-18 2-fluor-phenyl CH2 CH2 - H

4-19 2,6-difluor-phenyl CH2 CH2 - H Verbindung Nr. 4-19, Solvent: [DMSOl,

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

Spektrometer: 399.95MHz-'8,3762 (1 ,84) 8,3617 (3,57); 8,3473 (1 ,83); 7,6858 (15,23) 7,6731 (15,98); 7,3627 (1 , 16); 7,3459 (2,52) 7,3418 (2,17); 7,3289 (1 ,79); 7,325 (4,81 ) 7,321 (1 ,91 ); 7,308 (2,29); 7,3041 (3,05) 7,2874 (1 ,45); 7,201 1 (16); 7,1884 (15,1 1 ) 7, 1023 (0,61 ); 7,0979 (0,9); 7,0858 (6,51 ) 7,0776 (1 ,25); 7,0659 (10, 15); 7,0547 (1 ,26) 7,0458 (5,46); 7,0333 (0,71 ); 7,03 (0,52) 3,4505 (3); 3,4337 (7,14); 3,4175 (7,17) 3,4006 (3,27); 3,3603 (0,48); 3,3506 (0,96) 3,3316 (197,25); 3,3076 (0,42); 2,9097 (4,61 ); 2,8922 (8,53); 2,8747 (4,12); 2,6762 (0,37); 2,6717 (0,52); 2,6671 (0,37); 2,5418 (14,06); 2,525 (1 ,6); 2,5202 (2,5); 2,51 17 (29,79); 2,5072 (59,77); 2,5026 (78,58) 2,4979 (56,22); 2,4934 (26,35); 2,3339 (0,37); 2,3293 (0,52); 2,3247 (0,36); -0,0002 (6,98)

4-20 2,6-dichlor-phenyl CH2 CH2 - H

4-21 3 -(trifluormethyl)-phenyl CH2 CH2 - H

4-22 4-(trifluormethyl)-phenyl CH2 CH2 - H

4-23 2-methyl-phenyl CH2 CH2 - H

4-24 2,4,6-trimethyl-phenyl CH2 CH2 - H

4-25 3 ,4-bismethoxy-phenyl CH2 CH2 - H

4-26 phenyl CH2 CH2 - H

4-27 4-chlor-phenyl C(CH2-CH2) CH2 - H

4-28 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

4-29 4-chlor-phenyl CH2 C(CH2-CH2) - H

4-30 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

4-31 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 4-32, Solvent: [DMSO] Spektrometer: 399.95MHz-'8,3422 (2,49) 8,3288 (4,8); 8,3156 (2,57); 7,7222 (12,7)

4-32 2,4-dichlor-phenyl 0 CH2 CH2 H 7,7094 (13,41 ); 7,5727 (1 1 ,06); 7,5663

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

(12,06); 7,3863 (5,61 ); 7,3799 (5,35); 7,3642 (7,64); 7,3577 (7,48); 7,2441 (12,4); 7,2298 (14,09); 7,2218 (10,16); 7,2171 (14,12); 4,2214 (7,21 ); 4,2069 (16); 4,1924 (8); 3,6582 (4,04); 3,6439 (1 1 ,17); 3,6297 (10,84); 3,6154 (3,67); 3,3273 (96,57); 2,6761 (0,38); 2,6718 (0,51 ); 2,6675 (0,39); 2,542 (5,91 ); 2,5246 (1 ,61 ); 2,5071 (57,98); 2,5027 (76,93); 2,4983 (58,65); 2,3339 (0,36); 2,3294 (0,48); 2,325 (0,37); -0,0002 (3,39)

4-33 4-chlor-phenyl CH2 CH2 CH2 H

4-34 4-chlor-phenyl NCH3 CH2 CH2 H

4-35 2,4-dichlor-phenyl NCH3 CH2 CH2 H

4-36 4-chlor-phenyl CH(OCH3) CH2 - H

4-37 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 4-38, Solvent: [DMSO], Spektrometer: 399.95MHz 8,3451 (2,74); 8,3316 (5,03); 8,3181 (2,84); 7,7043 (15,02); 7,6916 (15,87); 7,3568 (8,12); 7,3538 (8); 7,3442 (9,03); 7,341 1 (8,48); 7,2174 (16); 7,2047 (15,26); 6,9763 (6,01 ); 6,9677 (10, 12); 6,9638 (5,89); 6,9551 (10,17); 6,9408 (9,96); 6,9335 (6,3); 3,4995 (4,52); 3,4819 (10,28); 3,4671 (10,58); 3,4493 (5,31 ); 3,3305 (31 ,33); 3,0738 (9,05); 3,0558 (15,86); 3,0378 (7,85); 2,541 1 (5,79); 2,524 (0,86); 2,5063 (28,38); 2,5018 (37,56); 2,4974 (28,52); -0,0002 (0,8)

4-38 2-thienyl CH2 CH2 H

4-39 3-thienyl CH2 CH2 - H

4-40 2-furyl CH2 CH2 - H

4-41 3-furyl CH2 CH2 - H

4-42 phenyl CH2 CH2 CH(CH3) H

4-43 phenyl CH2 CH2 CH2 H

4-44 2-Cl-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

4-45 4-t-butyl-phenyl CH2 CH2 CH2 H

4-46 4-methyl-phenyl CH2 CH2 CH2 H

4-47 phenyl CH2 CH2 CH(CH2CH3) H

4-48 2-methoxy-phenyl CH2 CH2 CH2 H

4-49 2-methyl-phenyl CH2 CH2 CH2 H

4-50 3 -methyl-phenyl CH2 CH2 CH2 H

4-51 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 4-52, Solvent: [DMSO], Spektrometer: 399.95MHz->8,289 (3,25); 8,2754 (6,02); 8,2617 (3,36); 7,7312 (0,36); 7,7184 (0,45); 7,7002 (14,81 ); 7,6875

(15.63) ; 7,3533 (1 ,47); 7,3359 (3,65); 7,3329 (3,54); 7,3156 (6,68); 7,2952 (4,43); 7,278 (1 ,94); 7,2407 (0,44); 7,228 (0,48); 7,2108 (16); 7, 198 (15,4); 7,1445 (0,34); 7,1223 (0,48); 7,1034 (1 ,35); 7,0904 (9,74); 7,0708 (15,16); 7,0513 (8,19); 7,0373 (1 ,2); 6,5636 (0,55); 3,3363 (59,45); 3,2877 (4,72); 3,2706

(10.64) ; 3,2546 (10,82); 3,2377 (5,03); 2,721 1 (6,7); 2,7019 (1 1 ,21 ); 2,6825 (7,59); 2,5446 (8,86); 2,5095 (32,46); 2,5053 (42,82); 2,501 (33,42); 1 ,815 (2,56); 1 ,7961 (6,96); 1 ,7775 (9,62); 1 ,7588 (6,71 ); 1 ,7405 (2,35); -0,0002 (0,39)

4-52 2,6-difluor-phenyl CH2 CH2 CH2 H

4-53 4-chlor-phenyl CH2 CH2 CH2 H

4-54 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

4-55 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

4-56 2,6-dimethyl-phenyl CH2 CH2 CH2 H

4-57 2,5-dichlor-phenyl CH2 CH2 CH2 H

4-58 4-i-propoxy-phenyl CH2 CH2 CH2 H

4-59 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

4-60 4-methyl-phenyl CH2 CH2 CH(CH3) H

4-61 2-methyl-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

4-62 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

4-63 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

4-64 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

4-65 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

4-66 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

4-67 4-phenoxy-phenyl CH2 CH2 CH2 H

4-68 3-chlor-phenyl CH2 CH2 CH(CH3) H

4-69 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

4-70 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

4-71 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

4-72 4-methoxy-phenyl CH2 CH2 CH2 H

4-73 4-chlor-phenyl CH2 CH2 CH(CH3) H

4-74 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

4-75 4-fluor-phenyl CH2 CH2 CH2 H

4-76 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

4-77 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

4-78 2-chlor-phenyl CH2 CH2 CH2 H

4-79 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl WO-A 2007/060164

Verbindung Nr. 4-80, Solvent: [DMSO], Spektrometer: 399.95MHz->8,2883 (3,21 ); 8,2753 (5,82); 8,2622 (3,42); 7,6997 (14, 19); 7,6984 (1 3,56); 7,687 (14,99); 7,6858 (14,27); 7,3213 (9, 12); 7,3093 (9,89); 7,2101 (15,06); 7,209 (14,6); 7, 1974 (14,74); 7, 1962 (14, 13); 6,9542 (6,4); 6,9453 (9,34); 6,9423 (7,53); 6,9333 (8,71 ); 6,8987 (10,86); 6,8907 (8,47); 3,3289 (59,48); 3,2994 (5,47); 3,2828 (13,42); 3,2674 (1 3,55); 3,2509 (5,79); 2,9046 (9,38); 2,8856 (16); 2,8664 (10,3); 2,6709 (0,49); 2,541 1 (5,09); 2,5398 (4,82); 2,501 1 (68,2); 2,4974 (55,76); 2,3281 (0,44); 1 ,8989 (2,91 ); 1 ,881 (9,05); 1 ,8622 (12, 1 7);

4-80 2-thienyl CH2 CH2 CH2 H 1 ,844 (8,84); 1 ,8262 (2,7); -0,0002 (0,92); -

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² Y CAS- bzw. Patent-Nr.

0,0015(0,88)

Verbindung Nr.4-81, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2659 (1,89); 8,2521 (3,57); 8,2382 (1,87); 7,6881 (11,61); 7,6754 (12,18); 7,5003 (1,69); 7,494 (13,45); 7,4896 (4,69); 7,4777 (4,96); 7,4732 (16); 7,4671 (2,05); 7,2381 (13,04); 7,2173 (11,31); 7,2023 (12,33); 7,1896 (11,63); 4,0378 (0,54); 4,02 (0,55); 3,4707 (2,96); 3,4535 (6,6); 3,4383 (6,52); 3,4207 (3,18); 3,3229 (55,32); 2,8306 (5,69); 2,8126 (10,26); 2,7948 (5,12); 2,6751 (0,53); 2,6707 (0,71); 2,6662 (0,53); 2,5238 (2,53); 2,5104 (42,3); 2,5061 (82,96); 2,5017 (107,91); 2,4972 (78,3); 2,4929 (38,31); 2,3328 (0,51); 2,3283 (0,69); 2,324 (0,52); 1,9889 (2,44); 1,2584 (0,37); 1,2491 (0,34); 1,1925 (0,64); 1,1747 (1,25); 1,1569 (0,63); 0,0079 (1,74); -0,0002 (44,61); -0,0085

4-81 4-brom-phenyl CH2 CH2 H (1,59)

Verbindung Nr.4-82, Solvent: [DMSO], Spektrometer: 399.95MHz

7,6667 (2,46); 7,654 (2,62); 7,5355 (1,71); 7,3362 (2,54); 7,3317 (1,01); 7,3151 (3,63); 7,2185 (3,4); 7,1975 (2,5); 7,1805 (2,68); 7,1678 (2,52); 3,3365 (20,24); 3,3294 (25,49); 3,0901 (4,92); 2,5063 (12,56); 2,502 (15,88); 2,4976(11,94); 1,3354 (0,48); 1,314

4-82 4-chlor-phenyl CH2 C(CH3)2 H (16); -0,0002 (4,44)

Verbindung Nr.4-83, Solvent: [DMSO], Spektrometer: 399.95MHz-'7,6871 (2,66); 7,6797 (2,07); 7,675 (3,39); 7,5904 (1,85); 7,5854 (2,22); 7,3686 (0,59); 7,3636 (0,58); 7,3479 (1,79); 7,3428 (2,06); 7,3286 (3,03); 7,3078 (0,97); 7,1961 (2,31); 7,1834 (2,26); 3,3548 (62,71); 3,3461 (49,33); 3,3409 (49,17); 3,3339 (34,47); 3,2763 (5,46); 2,5073 (23,38); 2,5032 (31,78); 2,4991 (26,77); 1,9891 (1); 1,3507 (16); 1,1752

4-83 2,4-dichlor-phenyl CH2 C(CH3)2 H (0,54); -0,0002 (7,13)

Verbindung Nr.4-84, Solvent: [DMSO],

Spektrometer: 399.95MHz

4-84 2-(trifluormethyl)-4-chlorphenyl CH2 CH2 H 8,383 (2,04); 8,3687 (3,97); 8,3546 (1,99);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

8,3164 (0,35); 7,7528 (6,84); 7,7474 (9,86); 7,7346 (4,64); 7,7293 (2,73); 7,714 (5,2); 7,7084 (4,18); 7,6994 (15,25); 7,6866 (15,78); 7,5619 (6,76); 7,5412 (5,43); 7,2103 (16); 7,1976 (15,19); 7,187 (0,43); 7,1816 (0,43); 5,7568 (1,06); 3,509 (2,76); 3,4923 (6,41); 3,4763 (6,43); 3,4591 (3,03); 3,323 (95,71); 3,3035 (4,12); 3,2952 (0,44); 3,2857 (3,28); 3,0133 (4,15); 2,996 (7,49); 2,9784 (3,61); 2,6956 (13,62); 2,6802 (0,39); 2,6758 (0,78); 2,6712(1 ,07); 2,6666 (0,76); 2,6621 (0,35); 2,5246 (3,29); 2,5199 (5,09); 2,5113 (57,87); 2,5067 (115,78); 2,5021 (152,53); 2,4975 (109,23); 2,493 (50,69); 2,3381 (0,36); 2,3335 (0,75); 2,3289 (1,01); 2,3243 (0,72); 2,3198 (0,33); 2,1972 (1,42); 2,1773 (2,71); 2,1569 (1,91); 1,9391 (0,72); 1,9208 (1,87); 1,9176(1,37); 1,9118(0,34); 1,9024 (1,96); 1,8994 (1,59); 1,8852 (0,65); 1,8823 (1,68); 1,8792 (0,77); 1,8635 (0,5); 1,3358 (4,81); 1,2984 (0,49); 1,2586 (0,86); 1,2495 (5,9); 1,2344 (1,02); 1,1874 (1,93); 0,008 (1 ,56); -0,0002 (47,94); -0,0085 (1 ,37)

Verbindung Nr.4-85, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3095 (0,73); 8,2956 (1,36); 8,2814 (0,7); 7,6991 (3,86); 7,6864 (4); 7,2124 (4,09); 7,1997 (3,94); 7,1915 (0,59); 7,1826 (4,31) 7,1599 (4,68); 7,1511 (0,53); 6,7634 (4,39) 6,7406 (3,91); 3,4974 (1,23); 3,4807 (2,99) 3,4642 (2,31); 3,3992 (1,39); 3,3836 (2,95) 3,3677 (3,11); 3,3355 (303,57); 3,2852 (0,41); 3,2753 (0,34); 2,9276 (16); 2,676 (0,43); 2,6715 (0,57); 2,5417 (28,45); 2,5068 (68,26); 2,5024 (86,24); 2,4979 (63,01); 2,3337 (0,41); 2,3293 (0,56); 2,3247 (0,41); 0,0078 (0,65); -0,0002 (13,43); -0,0084

4-85 4-chlor-phenyl N(CH3) CH2 CH2 H

Verbindung Nr.4-86, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3159 (1,13); 8,3109 (1,84); 8,2967 (3,57); 8,2828 (1,84); 7,7891 (7,25); 7,7689 (8,48); 7,7483 (0,44); 7,6916 (15,23); 7,6789 (16); 7,6296 (8,18); 7,546 (0,53); 7,4507 (4,39);

4-86 3-chlor-4-(trifluormethyl)-phenyl CH2 CH2 H 7,4307 (3,86); 7,358 (0,32); 7,2005 (15,96);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

7, 1877 (15,29); 3,539 (2,93); 3,5219 (7,7); 3,5073 (7,92); 3,4905 (3,23); 3,3239 (53,87); 3,2047 (0,7); 3,1898 (0,72); 2,9553 (4,99); 2,9383 (9,85); 2,9212 (4,4); 2,7977 (0,33); 2,7802 (0,59); 2,6765 (0,5); 2,6718 (0,68); 2,6672 (0,49); 2,5251 (2,19); 2,5204 (3,32); 2,51 18 (37,85); 2,5073 (76,06); 2,5027 (100,26); 2,4981 (71 ,49); 2,4935 (33,32); 2,3341 (0,47); 2,3295 (0,64); 2,3249 (0,44); 1 ,336 (3,03); 1 ,3299 (5,74); 1 ,299 (0,49); 1 ,2697 (0,39); 1 ,2589 (0,85); 1 ,2498 (2,68); 1 ,2339 (0,51 ); 1 ,21 16 (0,42); 1 ,188 (0,49)

Verbindung Nr. 4-87, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2897 (2,17); 8,276 (4,12); 8,2624 (2, 16); 7,736 (8,36); 7,7315 (8,67); 7,6972 (15,06); 7,6844 (15,74); 7,6656 (5,48); 7,645 (10,25); 7,6029 (5,8); 7,5986 (5,48); 7,5824 (3,08); 7,5779 (2,96); 7,2045 (16); 7,1918 (15,22); 5,7641 (0,79); 3,5293 (3,38); 3,5124 (8,83); 3,4976 (9); 3,481 (3,6); 3,3339 (42,56); 2,9747 (0,38); 2,9521 (6,46); 2,9352 (12,81 ); 2,9181 (5,67); 2,6835 (0,35); 2,6789 (0,47); 2,6743 (0,35); 2,5321 (1 ,78); 2,5188 (26,97); 2,5144 (53,04); 2,5098 (69,14); 2,5052 (49,99); 2,5007 (23,99); 2,3365 (0,43);

4-87 4-chlor-3-(trifluormethyl)-phenyl CH2 CH2 H 1 ,9964 (0,51 ); 1 ,3435 (0,51 ); 1 ,2563 (0,69)

Verbindung Nr. 4-88, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8748 (1,62); 7,8251 (1,38); 7,8201 (1,46); 7,6895 (2,54); 7,6769 (2,47); 7,6643 (0,8); 7,6599 (0,74); 7,3646 (1,25); 7,343 (1,13); 7,1933 (2,36); 7,1806 (2,22); 4,3632 (4,84); 3,3302 (38,37); 2,5421 (4,27); 2,5251 (0,4); 2,5117 (8,48); 2,5074 (16,74); 2,5029 (21,85); 2,4984 (16,2); 2,4944 (8,12); 1,4942 (16);

4-88 2-chlor-4-(trifluormethyl)-phenyl 0 CH2 C(CH3)2 H 1,4718 (0,33); 1,4664 (0,61)

Verbindung Nr. 4-89, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8044 (1,53); 7,7025 (0,59); 7,6957 (0,8); 7,6883 (2,87); 7,6803 (0,7); 7,6755 (3,55); 7,6604 (1,81); 7,6539 (1,1); 7,3165 (1,19); 7,2943 (1,07); 7,1974 (2,96); 7,1847 (2,85);

4-89 4-chlor-2-(trifluormethyl)-phenyl 0 CH3 C(CH3)3 H 4,3156 (4,63); 3,3281 (49,55); 2,5417 (6,3);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

2,5248 [0,58); 2,52 [0,91); 2,5115 [11,41); 2,5069 [22,83); 2,5023 [29,89); 2,4977 [21,3); 2,4932 [9,93); 1,4545 [16); 1,4259 [0,69)

Verbindung Nr. 4-90, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3684 [1,98); 8,3548 [3,86); 8,3416 [2,02); 7,8377 (7,1); 7,8328 [7,68); 7,7229 [15,04); 7,7102 (16); 7,7044 [3,72); 7,6989 (3,42); 7,6814 (4,1); 7,6771 (3,85); 7,6674 [0,48); 7,5236 (0,32); 7,5183 [0,34); 7,4413 (0,38); 7,4093 [6,44); 7,3876 (5,68); 7,2302 (15,98); 7,2175 [15,09); 4,3275 (5,82); 4,3131 [12,95); 4,2988 (6,26); 3,6945 [3,18); 3,6803 (9,06); 3,6662 [8,84); 3,652 (3); 3,365 [0,37); 3,3286 (261,25); 2,6806 [0,33); 2,6762 (0,72); 2,6716 [0,97); 2,6671 (0,7); 2,5419 [19,71); 2,525 (2,86); 2,5202 [4,63); 2,5117 (56,62); 2,5072 (112,56); 2,5026 (146,97); 2,498 (105,33); 2,4935 (49,52); 2,3385 [0,34); 2,3339 (0,7); 2,3294 [0,94); 2,3248 (0,68); 1,2343 [0,52); -

4-90 2-chlor-4-(trifluormethyl)-phenyl 0 CH2 CH2 H 0,0002 (1,06)

Tabelle 5

Verbindungen der Formel 1-5

Tabelle 6

Verbindungen der Formel 1-6

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

6-1 3 -methyl-2-thienyl CH2 CH2 - H

Verbindung Nr. 6-2, Solvent: [DMSO], Spektrometer: 399.95MHz

7,6931 (5,88); 7,6793 (6,1 1 ); 7,5677 (4,29); 7,5625 (4,38); 7,5055 (0,8); 7,491 1 (1 ,52); 7,4767 (0,79); 7,4167 (2,38); 7,396 (5,89); 7,3731 (4,19); 7,3679 (3,82); 7,3525 (1 ,62); 7,3472 (1 ,61 ); 7,1 121 (6,09); 7,0982 (5,83); 4,2841 (2,28); 4,2666 (7,51 ); 4,2491 (7,58); 4,2317 (2,34); 3,3386 (81 ,64); 3,3287 (4,96); 3,3131 (3,75); 3,2963 (1 ,48); 2,7431 (2,5); 2,7244 (3,13); 2,7046 (2,67); 2,5439 (4,54); 2,5271 (0,54); 2,5223 (0,86); 2,5137 (9,69); 2,5092 (19,29); 2,5046 (25,6); 2,5 (18,54); 2,4954 (8,72); 1 ,8254 (0,72); 1 ,8079 (1 ,93); 1 ,7888 (2,4); 1 ,77 (1 ,87); 1 ,7525 (0,63); 1 ,3855 (7,72); 1 ,3681 (16); 1 ,3506 (7,5); -0,0002 (0,89)

6-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

6-3 4-chlor-phenyl CH2 CH2 - H

6-4 2,4-dichlor-phenyl CH2 CH2 - H

6-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

6-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

[DMSO]: 7.69, d, 1H; 7.37, d, 2H; 7.25, d, 2H; 7.18, d, NH; 7.09, d, 1H; 4.25-4.14, m, 3H; 2.82, d, 2H; 1.29, t, 3H; 1.14, d, 3H

6-7 4-chlor-phenyl CH(CH3) CH2 - H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L Y Patent-Nr.

6-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

6-9 4-chlor-phenyl CH2 CH(CH3) - H

6-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

6-11 4-chlor-phenyl C(CH3)2 CH2 - H

6-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H

6-13 2-chlor-phenyl CH2 CH2 - H

6-14 3 ,4-dichlor-phenyl CH2 CH2 - H

6-15 3,5- dichlor-pheny 1 CH2 CH2 - H

6-16 3-chlor-phenyl CH2 CH2 - H

6-17 2-fluor-phenyl CH2 CH2 - H

6-18 2,6-difluor-phenyl CH2 CH2 - H

6-19 2,6-dichlor-phenyl CH2 CH2 - H

6-20 3 -(trifluormethyl)-phenyl CH2 CH2 - H CAS: 1022443-07-7

6-21 4-(trifluormethyl)-phenyl CH2 CH2 - H

6-22 2-methyl-phenyl CH2 CH2 - H

6-23 2,4,6-trimethyl-phenyl CH2 CH2 - H

6-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H

6-25 phenyl CH2 CH2 - H

6-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

6-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

6-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

6-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

6-30 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 6-31 , Solvent: [DMSO], Spektrometer:

399.95MHz

7,7264 (5,52); 7,7126 (5,85); 7,6937 (1 ,09); 7,6796

(2, 14); 7,6653 (1 , 1 3); 7,5916 (5,02); 7,5851 (5,41 );

7,3872 (2,53); 7,3807 (2,41 ); 7,365 (3,43); 7,3586

(3,35); 7,2439 (5,76); 7,2216 (4,3); 7, 1218 (5,95);

6-31 2,4-dichlor-phenyl 0 CH2 CH2 H 7, 108 (5,75); 4,2743 (2,4); 4,2568 (7,71 ); 4,2393

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

(7,81 ); 4,2218 (2,54); 4,1994 (3,23); 4,1857 (6,99); 4, 1721 (3,66); 3,7205 (1 ,81 ); 3,7067 (4,99); 3,6927 (4,87); 3,6788 (1 ,67); 3,3285 (79,46); 2,5424 (7,29); 2,5254 (0,83); 2,51 17 (17,49); 2,5076 (34,69); 2,5031 (46,14); 2,4987 (35,2); 1 ,3303 (7,85); 1 ,3128 (16); 1 ,2954 (7,69); -0,0002 (1 ,17)

6-32 4-chlor-phenyl CH2 CH2 CH2 H

6-33 4-chlor-phenyl NCH3 CH2 CH2 H

6-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

6-35 4-chlor-phenyl CH(OCH3) CH2 - H

6-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 6-37, Solvent: [DMSO], Spektrometer: 399.95MHz

7,6972 (5,59); 7,6834 (5,88); 7,5202 (1 ,04); 7,5062 (1 ,95); 7,4922 (1 ,09); 7,3773 (3,09); 7,3745 (3,05); 7,3646 (3,39); 7,3617 (3,18); 7,0945 (6,15); 7,0806 (5,93); 6,9891 (2,46); 6,9805 (3,59); 6,9765 (2,5); 6,9678 (3,37); 6,9381 (3,6); 6,9305 (2,69); 4,2217 (2,47); 4,2041 (7,85); 4,1866 (7,97); 4, 1692 (2,6); 3,5802 (1 ,96); 3,5634 (5,28); 3,5481 (5,52); 3,5315 (2,23); 3,3282 (54,19); 3,0541 (3,58); 3,0371 (7); 3,0201 (3,22); 2,5064 (28,37); 2,502 (37,77); 2,4976 (28,92); 1 ,2767 (7,89); 1 ,2592 (16); 1 ,2417 (7,77); - 0,0002 (0,57)

6-37 2-thienyl CH2 CH2 H

6-38 3-thienyl CH2 CH2 - H

6-39 2-furyl CH2 CH2 - H

6-40 3-furyl CH2 CH2 - H

6-41 phenyl CH2 CH2 CH(CH3) H

6-42 phenyl CH2 CH2 CH2 H

6-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

6-44 4-t-butyl-phenyl CH2 CH2 CH2 H

6-45 4-methyl-phenyl CH2 CH2 CH2 H

6-46 phenyl CH2 CH2 CH(CH2CH3) H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

6-47 2-methoxy-phenyl CH2 CH2 CH2 H

6-48 2-methyl-phenyl CH2 CH2 CH2 H

6-49 3 -methyl-phenyl CH2 CH2 CH2 H

6-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 6-51 , Solvent: [DMSO], Spektrometer: 399.95MHz

7,6975 (5,44); 7,6837 (5,71 ); 7,5395 (1 ,16); 7,5254 (2,18); 7,51 13 (1 ,2); 7,3505 (0,57); 7,3333 (1 ,35); 7,33 (1 ,3); 7,3127 (2,54); 7,2921 (1 ,67); 7,2751 (0,75); 7, 1 166 (6,24); 7,1028 (6,27); 7,091 (3,65); 7,0712 (5,73); 7,0514 (2,99); 7,038 (0,41 ); 4,2897 (2,53); 4,2722 (7,97); 4,2547 (8,09); 4,2373 (2,63); 3,332 (25,51 ); 3,3187 (2,12); 3,302 (4,8); 3,2862 (4,85); 3,2697 (1 ,88); 2,6936 (2,46); 2,6748 (4,71 ); 2,656 (2,72); 2,5441 (0,45); 2,509 (18,73); 2,5046 (24,99); 2,5003 (19,41 ); 1 ,7933 (0,94); 1 ,7757 (2,93); 1 ,7569 (3,9); 1 ,7387 (2,84); 1 ,7212 (0,84); 1 ,3934 (7,91 ); 1 ,3759 (16); 1 ,3664 (1 ,16); 1 ,3584 (7,85); -0,0002 (0,45)

6-51 2,6-difluor-phenyl CH2 CH2 CH2 H

6-52 4-chlor-phenyl CH2 CH2 CH2 H

6-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

6-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

6-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

6-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

6-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

6-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

6-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

6-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

6-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

6-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

6-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

6-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

6-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

6-66 4-phenoxy-phenyl CH2 CH2 CH2 H

6-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

6-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

6-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

6-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

6-71 4-methoxy-phenyl CH2 CH2 CH2 H

6-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

6-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

6-74 4-fluor-phenyl CH2 CH2 CH2 H

6-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

6-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

6-77 2-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 6-78, Solvent: [DMSO], Spektrometer: 399.95MHz

7,696 (5,55); 7,6822 (5,86); 7,4984 (1 ,13); 7,4843

(2,09); 7,4701 (1 ,17); 7,325 (3,18); 7,3232 (2,97); 7,3223 (3,01 ); 7,3122 (3,52); 7,3104 (3,17); 7,3095 (3,19); 7, 1 147 (6,22); 7,1008 (5,96); 6,9534 (2,59); 6,9448 (3,55); 6,9408 (2,68); 6,9322 (3,22); 6,8846 (3,65); 6,8775 (2,97); 4,2878 (2,52); 4,2703 (7,94); 4,2528 (8,07); 4,2354 (2,65); 3,347 (2,19); 3,3295

(31 ,18); 3,3146 (5,41 ); 3,2979 (2,23); 2,861 1 (3,39); 2,842 (5,86); 2,8229 (3,7); 2,5246 (0,61 ); 2,5069 (19,67); 2,5026 (25,81 ); 2,4984 (19,91 ); 1 ,8865 (1 ,08); 1 ,8686 (3,25); 1 ,8498 (4,32); 1 ,8316 (3,17); 1 ,8137 (1 ); 1 ,3951 (7,95); 1 ,3776 (16); 1 ,3601 (7,86); -0,0002 (0,45)

6-78 2-thienyl CH2 CH2 CH2 H

Tabelle 7

Verbindungen der Formel 1-7

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7-1 3 -methyl-2-thienyl CH2 CH2 - H

7-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

[DMSO], Spektrometer: 399,95MHz

8,7637 (1 ,66); 8,7502 (3,17); 8,7364 (1 ,7); 7,9252 (10,03); 7,9123 (10,75); 7,5535 (10,65); 7,5407 (10,07) 7,3609 (8,8); 7,3562 (3,53); 7,3448 (4,38); 7,3398 (16) 7,334 (2,76); 7,2856 (13,93); 7,2645 (8, 1); 3,4844 (2,63) 3,4672 (5,67); 3,4522 (5,54); 3,4342 (2,92); 3,3357 (35,3); 2,8535 (5,02); 2,8353 (8,73); 2,8174 (4,53) 2,6767 (0,4); 2,6723 (0,55); 2,6679 (0,42); 2,5256 (1 ,69) 2,51 19 (27,98); 2,5077 (55,22); 2,5032 (72,9); 2,4987 (54,91); 2,4945 (28,18); 2,3347 (0,34); 2,33 (0,48) 2,3255 (0,35); 0,0079 (0,49); -0,0002 (13,72); -0,0084

7-3 4-chlor-phenyl CH2 CH2 H (0,58)

[DMSO], Spektrometer: 399,95MHz

8,791 (1 ,29); 8,7773 (2,55); 8,7634 (1,36); 7,9238 (7,38) 7,91 1 (7,94); 7,5902 (5,62); 7,5516 (7,8); 7,5388 (7,38) 7,392 (0,43); 7,3731 (16); 7,3526 (0,37); 7,3486 (0,5) 5,7585 (0,68); 3,51 17 (1 ,9); 3,4947 (4,75); 3,4796 (4,87) 3,4626 (2,18); 3,4101 (0,4); 3,3554 (231 ,44); 2,9775 (3,9); 2,96 (7,5); 2,9426 (3,52); 2,6739 (0,39); 2,5272 (1 ,22); 2,5135 (21, 16); 2,5094 (42, 13); 2,5049 (55,83) 2,5004 (42,57); 2,4962 (22,27); 2,3316 (0,38); 1 ,3362 (0,33); 1 ,2493 (0,41); 0,0079 (0,4); -0,0002 (10,88);

7-4 2,4-dichlor-phenyl CH2 CH2 H 0,0084 (0,49)

7-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

7-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

7-7 4-chlor-phenyl CH(CH3) CH2 - H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

7-9 4-chlor-phenyl CH2 CH(CH3) - H

7-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

7-11 4-chlor-phenyl C(CH3)2 CH2 - H

7-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H

7-13 2-chlor-phenyl CH2 CH2 - H

7-14 3 ,4-dichlor-phenyl CH2 CH2 - H

7-15 3,5- dichlor-pheny 1 CH2 CH2 - H

7-16 3-chlor-phenyl CH2 CH2 - H

7-17 2-fluor-phenyl CH2 CH2 - H

[DMSO], Spektrometer: 399,95MHz

8,8536 (2,47); 8,8394 (4,77); 8,8253 (2,54); 7,9229 (14,9); 7,9101 (15,96); 7,552 (16); 7,5391 (15,07); 7,3681 (1 ,28); 7,3512 (2,93); 7,3473 (2,78); 7,3303 (5,68); 7,3131 (2,98); 7,3096 (3,65); 7,2927 (1 ,65); 7,1043 (0,78); 7,0998 (1 ,07); 7,0876 (8,02); 7,0679 (12,59); 7,057 (1 ,95); 7,048 (6,83); 7,0356 (1 ,02); 5,7606 (0,46); 3,4601 (3,72); 3,4432 (9,39); 3,4273 (9,56); 3,4105 (4,19); 3,3369 (50,68); 2,9207 (5,93); 2,9033 (1 1,25); 2,8858 (5,46); 2,6772 (0,44); 2,6729 (0,61); 2,6685 (0,45); 2,5261 (2,15); 2,5125 (34,74); 2,5083 (68,66); 2,5038 (90,7); 2,4993 (68,58); 2,495 (35,71); 2,3349 (0,43); 2,3305 (0,61); 2,326 (0,45); 1 ,3363 (0,51); 1 ,2496

7-18 2,6-difluor-phenyl CH2 CH2 H (0,6); 0,0079 (0,6); -0,0002 (16,59); -0,0084 (0,78)

[DMSO], Spektrometer: 399,95MHz

8,8706 (1 ,58); 8,8566 (3,12); 8,8422 (1 ,63); 7,923 (9,28); 7,9102 (9,9); 7,5517 (10, 16); 7,5388 (9,57); 7,4689 (1 1,6); 7,4489 (16); 7,4285 (0,32); 7,3095 (5,44); 7,2903 (5,71); 7,2884 (5,66); 7,2803 (0,56); 7,2692 (3,63); 7,2618 (0,38); 5,7598 (1 ,47); 3,5105 (2,09); 3,4939 (5,53); 3,4771 (5,61); 3,4609 (2,57); 3,3736 (0,52); 3,3434 (148,2); 3,189 (4,65); 3,1712 (8,14); 3,154 (3,8); 2,9768 (0,44); 2,6733 (0,43); 2,6688 (0,33); 2,5086 (47,99); 2,5042 (63,51); 2,4997 (48,43); 2,4956 (25,51); 2,331 (0,42); 1 ,2494 (0,37); -0,0002 (8,94); -0,0084

7-19 2,6-dichlor-phenyl CH2 CH2 H (0,43)

7-20 3 -(trifluormethyl)-phenyl CH2 CH2 - H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7-21 4-(trifluormethyl)-phenyl CH2 CH2 - H

7-22 2-methyl-phenyl CH2 CH2 - H

7-23 2,4,6-trimethyl-phenyl CH2 CH2 - H

7-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H

7-25 phenyl CH2 CH2 - H

7-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

7-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

7-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

7-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

7-30 4-chlor-phenyl 0 CH2 CH2 H

[DMSO], Spektrometer: 399,95MHz

8,8522 (1,07); 8,8389 (2,09); 8,8258 (1,1); 8,1029 (1,26); 8,0993 (1,04); 8,0903 (1,05); 8,0868 (1,31); 7,9491 (6,61); 7,9363 (7,1); 7,919 (0,55); 7,6307 (0,37); 7,5719 (14,11); 7,5656 (7,94); 7,5591 (7,26); 7,5441 (0,38); 7,5377 (0,35); 7,5041 (0,57); 7,4912 (0,49); 7,3874 (2,9); 7,3809 (2,79); 7,3773 (1,56); 7,3705 (1,38); 7,3652 (4,09); 7,3587 (4,04); 7,3551 (2,09); 7,3485 (1,63); 7,3406 (0,34); 7,3351 (0,33); 7,2462 (6,01); 7,2239 (4,49); 7,2093 (0,34); 7,1932 (0,47); 7,1872 (2,26); 7,1649 (1,81); 6,5864 (1,34); 6,5827 (1,08); 6,5777 (0,8); 6,574 (1,09); 6,5702 (1,33); 5,7607 (1,41); 4,3737 (0,33); 4,2346 (3,15); 4,2201 (7,07); 4,2057 (3,51); 4,1882 (0,39); 4,1142 (0,42); 4,1045 (0,37); 4,0894 (0,39); 4,0184 (1,55); 4,0041 (3,2); 3,9898 (1,62); 3,7464 (0,48); 3,6652 (1 5); 3,6511 (4,89); 3,637 (4,76); 3,6227 (1,68); 3,5065 (0,59); 3,4891 (0,33); 3,3356 (11,99); 3,0722 (0,34); 3,0672 (0,41); 3,0541 (0,37); 2,9425 (16); 2,9058 (1,58); 2,8915 (3,16); 2,8771 (1,58); 2,677 (0,39); 2,6725 (0,55); 2,668 (0,4); 2,5259 (1,55); 2,5122 (30,72); 2,5079 (61,96); 2,5034 (82,32); 2,4989 (62,24); 2,4946 (32,17); 2,4309 (0,33); 2,3481 (0,55); 2,3303 (0,78); 2,3257 (0,52); 2,1891 (0,75); 2,1818 (3,87); 2,1725 (0,55); 2,0965 (0,49); 2,0722 (3,69); 2,0592 (1,1); 1,8245 (0,48); 1,7375 (2,42); 1,6581 (0,35); 1,325 (0,48); 1,2271 (6,23); 1,1838 (0,45); 1,1659 (0,92); 1,148 (0,44); 1,0533 (0,61); 1,0352 (1,28); 1,0171 (0,58); 0,9532 (1,71); 0,9368

7-31 2,4-dichlor-phenyl 0 CH2 CH2 H (1,74); 0,0079 (0,58); -0,0002 (17,26); -0,0085 (0,78)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7-32 4-chlor-phenyl CH2 CH2 CH2 H

7-33 4-chlor-phenyl NCH3 CH2 CH2 H

7-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

7-35 4-chlor-phenyl CH(OCH3) CH2 - H

7-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 7-37, Solvent: [DMSO], Spektrometer: 399.95MHz

8,839 (2,59); 8,8256 (4,79); 8,8124 (2,64); 8,3189 (0,4); 7,9395 (14,92); 7,9266 (16); 7,5661 (15,86); 7,5532 (14,91); 7,3585 (7,66); 7,3555 (7,79); 7,3459 (8,58); 7,3429 (8,24); 6,9743 (6,13); 6,9657 (9,59); 6,9617 (6,17); 6,9531 (9,46); 6,9321 (9,27); 6,9259 (6,25); 3,5065 (4,36); 3,4888 (10,03); 3,4742 (10,22); 3,4564 (5,21); 3,3375 (161 ,8); 3,0819 (8,6); 3,064 (15,33); 3,046 (7,4); 2,6765 (0,71); 2,672 (0,95); 2,6676 (0,73); 2,5252 (3,1 1); 2,5074 (102,9); 2,503 (135,05); 2,4985 (102,17); 2,334 (0,66); 2,3298 (0,9); 2,3252 (0,67); 1 ,336 (0,54); 1 ,2493 (0,67); 0,0079 (0,65); -0,0002 (17,56); -0,0083

7-37 2-thienyl CH2 CH2 H (0,81)

7-38 3-thienyl CH2 CH2 - H

7-39 2-furyl CH2 CH2 - H

7-40 3-furyl CH2 CH2 - H

7-41 phenyl CH2 CH2 CH(CH3) H

7-42 phenyl CH2 CH2 CH2 H

7-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

7-44 4-t-butyl-phenyl CH2 CH2 CH2 H

7-45 4-methyl-phenyl CH2 CH2 CH2 H

7-46 phenyl CH2 CH2 CH(CH2CH3) H

7-47 2-methoxy-phenyl CH2 CH2 CH2 H

7-48 2-methyl-phenyl CH2 CH2 CH2 H

7-49 3 -methyl-phenyl CH2 CH2 CH2 H

7-50 3-chlor-phenyl CH2 CH2 CH2 H

[DMSO], Spektrometer: 399,95MHz

7-51 2,6-difluor-phenyl CH2 CH2 CH2 H 8,7549 (2,05); 8,7414 (3,86); 8,7278 (2,09); 8,3188

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

(0,37); 7,9666 (0,33); 7,9538 (0,41); 7,9341 (14,91); 7,9269 (0,85); 7,9212 (15,91); 7,5855 (0,37); 7,5726 (0,39); 7,5573 (16); 7,5444 (15,04); 7,3519 (1 ,2); 7,335 (2,69); 7,331 1 (2,41); 7,3141 (5,04); 7,3104 (2,27); 7,2967 (2,47); 7,2933 (3,34); 7,2765 (1 ,51); 7,105 (0,76); 7, 1006 (0,94); 7,088 (6,68); 7,0679 (10,99); 7,0559 (1 ,48); 7,0478 (5,67); 7,0347 (0,81); 6,5468 (0,52); 3,3468 (249,02); 3,2962 (3,34); 3,2789 (6,79); 3,2634 (6,76); 3,246 (3,44); 2,7069 (4,52); 2,6878 (7,65); 2,6688 (5,31); 2,5441 (0,41); 2,5273 (1 ,94); 2,5225 (2,98); 2,5139 (33,76); 2,5094 (68,38); 2,5049 (90,84); 2,5003 (67,84); 2,4959 (34,13); 2,3361 (0,43); 2,3317 (0,61); 2,3271 (0,44); 1 ,8234 (1 ,73); 1,8044 (4,61); 1 ,786 (6,51); 1 ,7672 (4,31); 1 ,7488 (1 ,53); 1 ,3367 (0,51); 1 ,2498 (0,63); 0,008 (0,5); -0,0002 (15,55); -0,0085 (0,6)

[DMSO], Spektrometer: 399,95MHz

8,7403 (1 ,6); 8,7272 (2,97); 8,7136 (1,63); 7,9373 (9,86); 7,9244 (10,54); 7,5592 (10,41); 7,5463 (9,86); 7,3552

(1.07) ; 7,3492 (8,86); 7,3444 (3,56); 7,3331 (4,47); 7,3281 (16); 7,3223 (2,8); 7,309 (0,44); 7,273 (14); 7,2519 (8,27); 7,2312 (0,34); 3,345 (103,91); 3,2734 (2,65); 3,2562 (6,23); 3,2416 (6,24); 3,2245 (2,8); 2,678 (0,38); 2,6736 (0,52); 2,6593 (4,6); 2,6406 (7,03); 2,621

(5.08) ; 2,5271 (1 ,2); 2,5135 (20, 13); 2,5092 (40,08); 2,5047 (52,88); 2,5002 (39,87); 2,4959 (20,52); 2,3314 (0,35); 1 ,8483 (1 ,39); 1 ,8303 (4); 1 ,81 14 (5,31); 1 ,793 (3,88); 1 ,7751 (1,25); 1 ,337 (0,39); 1,2494 (0,47); -0,0002

7-52 4-chlor-phenyl CH2 CH2 CH2 H (7,86); -0,0084 (0,33)

7-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

7-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

7-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

7-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

7-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

7-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

7-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

7-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

7-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

7-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

7-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

7-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

7-66 4-phenoxy-phenyl CH2 CH2 CH2 H

7-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

7-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

7-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

7-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

7-71 4-methoxy-phenyl CH2 CH2 CH2 H

7-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

7-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

7-74 4-fluor-phenyl CH2 CH2 CH2 H

7-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

7-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

7-77 2-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 7-78, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7475 (0,68); 8,7339 (1 ,34); 8,7201 (0,71); 7,9284 (3,31); 7,9155 (3,52); 7,554 (3,57); 7,5412 (3,35); 7,1828 (0,44); 7,1742 (4,37); 7, 1691 (1 ,48); 7, 1516 (4,8); 7,1428 (0,53); 6,7631 (0,63); 6,7544 (4,51); 6,7318 (4,02); 6,7229 (0,47); 3,5155 (1 ,15); 3,4986 (2,94); 3,4826 (2,24); 3,4183 (1 ,22); 3,4033 (2,51); 3,3878 (2,05); 3,3716 (0,74); 3,3307 (60,01); 2,9199 (16); 2,8746 (0,79); 2,542 (19); 2,507 (25, 15); 2,5027 (31,73); 2,4983 (23,27);

7-78 4-chlor-phenyl N(CH3) CH2 CH2 H 2,3743 (0,39); -0,0002 (3,58)

Tabelle 8

Verbindungen der Formel 1-8

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

8-1 3 -methyl-2-thienyl CH2 CH2 - H

Verbindung Nr. 8-2, Solvent: [DMSO], Spektrometer: 399.95MHz 8,2244 (0,52); 8,2099 (1 ); 8,1955 (0,52); 7,6582 (2,82); 7,6541 (2,8); 7,5613 (3,05); 7,556 (3,13); 7,4276 (1 ,91 ); 7,4069 (3,86); 7,3725 (2,72); 7,3672 (2,5); 7,3518 (1 ,3); 7,3465 (1 ,28); 6,4852 (3); 6,481 1 (2,98); 3,337 (46,88); 3,254 (0,97); 3,2368 (2,09); 3,221 1 (2,08); 3,2039 (0,99); 2,7131 (1 ,76); 2,6946 (2,19); 2,6745 (1 ,94); 2,5436 (10,74); 2,5267 (0,35); 2,5219 (0,56); 2,5134 (6,94); 2,5089 (13,88); 2,5042 (18,41 ); 2,4996 (13,29); 2,4951 (6,22); 2,2699 (16); 1 ,8033 (0,5); 1 ,7844 (1 ,26); 1 ,7662 (1 ,7); 1 ,7479 (1 ,18); 1 ,7294 (0,44); -0,0002 (1 ,59)

8-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

8-3 4-chlor-phenyl CH2 CH2 - H CAS: 1330848-74-2

[DMSO], Spektrometer: 601.6MHz 8.2533 (0.55); 8.2437 (1.08); 8.2341 (0.56); 7.6534 (2.78); 7.6506 (2.81); 7.5762 (2.58); 7.5730 (2.69); 7.3713 (0.79); 7.3680 (0.66); 7.3575 (3.1 1); 7.3543 (3.31); 7.3480 (4.41); 7.3343 (1.03); 6.4800 (2.88); 6.4772 (2.88); 3.4549 (0.97); 3.4436 (1.99); 3.4330 (1.93); 3.4213 (1.06); 3.3283 (23.69); 2.9365 (1.93); 2.9244 (3.25); 2.9126 (1.79); 2.5434 (7.05); 2.5101 (3.42); 2.5071 (7.69); 2.5041 (10.83); 2.5010 (7.79);

8-4 2,4-dichlor-phenyl CH2 CH2 H 2.4980 (3.55); 2.2571 (16.00); -0.0002 (8.63)

8-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

Physikalische Daten: ¹ H-NMR, 6 |ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

8-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 601.6MHz 8.1009 (0.58); 8.0913 (1.1 1); 8.0817 (0.58); 7.6309 (2.83); 7.6281 (2.77); 7.3559 (0.46): 7.3515 (3.81); 7.3483 (1.30); 7.3407 (1.56); 7.3374 (5.63); 7.3332 (0.69); 7.2773 (0.73); 7.2731 (5.14); 7.2699 (1.46); 7.2621 (1.26); 7.2591 (3.56); 7.2547 (0.39); 6.4671 (2.96); 6.4644 (2.85); 3.381 1 (0.42); 3.3708 (0.53); 3.3689 (0.56); 3.3590 (1.16); 3.3489 (1.02); 3.3471 (1.10); 3.3367 (1.16); 3.3269 (67.15); 3.3167 (1.04); 3.3069 (0.97); 3.3042 (0.96); 3.2946 (1.27); 3.2851 (0.47); 3.2824 (0.52); 3.2728 (0.45); 3.0742 (0.56); 3.0622 (1.1 1); 3.0503 (1.09); 3.0384 (0.51); 2.5417 (12.80); 2.5233 (0.33); 2.5203 (0.40); 2.5171 (0.43); 2.5083 (7.97); 2.5054 (16.93); 2.5023 (23.20); 2.4993 (16.75); 2.4963 (7.73); 2.2443 (16.00): 1.1791 (7.28); 1.1675 (7.25); 0.0050 (0.39); -0.0002 (9.65); -0.0057

8-7 4-chlor-phenyl CH(CH3) CH2 H (0.32)

[DMSO], Spektrometer: 601.6MHz 8.1820 (0.66); 8.1723 (1.24); 8.1625 (0.64); 7.6318 (2.92); 7.6291 (2.79); 7.5490 (2.92); 7.5455 (2.93); 7.4479 (1.92); 7.4338 (3.89); 7.4107 (2.32); 7.4071 (2.09); 7.3967 (1.1 1); 7.3931 (1.08); 6.4670 (3.04); 6.4642 (2.92); 3.5460 (0.52); 3.5341 (1.13); 3.5223 (1.24); 3.5105 (0.69); 3.4201 (1.37); 3.4143 (1.36); 3.4096 (1.70); 3.4044 (1.53); 3.4019 (1.35); 3.3986 (1.21); 3.3919 (1.19); 3.3269 (69.14): 3.3091 (0.97); 2.5421 (9.32); 2.5236 (0.75); 2.5206 (0.93); 2.5175 (1.05); 2.5087 (9.41); 2.5058 (18.83); 2.5028 (25.35); 2.4997 (18.16); 2.4968 (8.55); 2.4842 (0.97); 2.2433 (16.00); 1.1680 (7.51); 1.1565 (7.49); 0.0050 (0.37); -

8-8 2,4-dichlor-phenyl CH(CH3) CH2 H 0.0002 (8.14); -0.0056 (0.33)

[DMSO], Spektrometer: 601.6MHz 7.9941 (1.08); 7.9798 (1.10); 7.6414 (2.71 ); 7.6386 (2.78); 7.3234 (0.34); 7.3191 (3.63); 7.3160 (1.24); 7.3084 (1.40); 7.3052 (5.46); 7.301 1 (0.68); 7.2467 (0.59); 7.2427 (4.72); 7.2396 (1.42); 7.2318 (1.12); 7.2287 (3.33); 7.2246 (0.39); 6.4645 (2.83); 6.4617 (2.85); 4.1700 (0.46); 4.1672 (0.56): 4.1562 (0.83); 4.1454 (0.58); 4.1426 (0.48); 3.3297 (1 11.93); 2.8835 (0.86); 2.8699 (0.86); 2.8610 (1.1 1 ): 2.8475 (1.08); 2.7225 (1.08); 2.7122 (1.1 1); 2.7001 (0.86); 2.6897

8-9 4-chlor-phenyl CH2 CH(CH3) H (0.83); 2.5418 (13.67); 2.5204 (0.33); 2.5085 (7.69);

Physikalische Daten: ^] H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7.5015 (2.66); 7.4981 (2.76); 7.2266 (1.51); 7.2232 (1.50); 7.2129 (1.39); 7.2096 (1.40); 6.4806 (2.86); 6.4778 (2.82); 3.4456 (1.01); 3.4340 (2.18); 3.4239 (2.16); 3.4122 (1.10); 3.3316 (204.25); 3.3131 (0.35); 2.8338 (1.79); 2.8219 (3.35); 2.8101 (1.68); 2.5418 (15.80); 2.5235 (0.42); 2.5204 (0.51); 2.5173 (0.47); 2.5084 (12.10); 2.5055 (27.47); 2.5024 (39.05); 2.4994 (28.35); 2.4964 (13.25); 2.2537 ( 16.00); -0.0002 (4.73)

[DMSO], Spektrometer: 601.6MHz 8.2134 (0.53); 8.2041 (1.03); 8.1946 (0.53); 7.6572 (2.71); 7.6544 (2.70); 7.4295 (1.39); 7.4264 (2.74); 7.4232 (1.50); 7.2998 (5.88); 7.2966 (5.65); 6.4830 (2.85); 6.4802 (2.76); 3.4567 (0.97); 3.4451 (2.22); 3.4350 (2.23); 3.4234 (1.06); 3.3345 (121.94); 2.8476 (1.71); 2.8359 (3.32); 2.8242 (1.61); 2.5426 (1 1.75); 2.5093 (6.44); 2.5063 (14.44); 2.5032 (20.30); 2.5002

8-15 3,5-dichlor-phenyl CH2 CH2 H (14.66); 2.4972 (6.66); 2.2543 (16.00); -0.0002 (3.03)

8-16 3-chlor-phenyl CH2 CH2 - H CAS: 1043374-79-3

8-17 2-fluor-phenyl CH2 CH2 - H CAS: 1043270-08-1

[DMSO], Spektrometer: 601.6MHz 8.2999 (0.51); 8.2901 (0.98); 8.2805 (0.51); 7.6472 (2.70); 7.6444 (2.68); 7.3275 (0.64); 7.3248 (0.61); 7.3136 (1.21); 7.3024 (0.64); 7.2998 (0.72); 7.0656 (1.69); 7.0526 (2.62); 7.0449 (0.34); 7.0394 (1.51); 6.4765 (2.83); 6.4737 (2.81); 3.4012 (0.93); 3.3903 (1.99); 3.3777 (1.95); 3.3672 (1.02); 3.3395 (142.03); 2.8751 (1.33); 2.8630 (2.35); 2.8512 (1.24); 2.5430 (13.70); 2.5097 (6.17); 2.5067 (13.45); 2.5036 (18.62); 2.5006 (13.27); 2.4976 (5.94); 2.2531 (16.00); -0.0002

8-18 2,6-difluor-phenyl CH2 CH2 H (0.79)

[DMSO], Spektrometer: 601.6MHz 8.3392 (0.53); 8.3294 (1.05); 8.3197 (0.54); 7.6538 (2.65); 7.651 1 (2.71 ); 7.4513 (5.52); 7.4379 (6.67); 7.2889 (2.12); 7.2756 (2.61 ); 7.2621 (1.59); 6.4793 (2.75); 6.4765 (2.82); 3.4316 (0.94); 3.4212 (1.85); 3.4172 (1.06); 3.4097 (1.51); 3.4071 (1.92); 3.3972 (1.09); 3.3352 (90.12); 3.3346 (94.30); 3.1452 (1.99); 3.1323 (2.48); 3.1207 (1.72); 2.5427 (10.35); 2.5094 (6.80); 2.5064 (15.36); 2.5034 (21.69); 2.5003 (15.57);

8-19 2,6-dichlor-phenyl CH2 CH2 H 2.4973 (7.13); 2.2610 (16.00); -0.0002 (4.04)

[DMSO], Spektrometer: 601.6MHz 8.2219 (0.57); 8.2125 (1.05); 8.2030 (0.56); 7.6499

8-20 3 -(trifluormethyl)-phenyl CH2 CH2 H (2.92); 7.6472 (2.84); 7.5688 (2.78); 7.5578 (0.96);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

7.5546 (1.52); 7.5401 (2.57); 7.5376 (3.85); 7.5253 (1.05); 6.4792 (3.00); 6.4764 (2.89); 3.4759 (1.07); 3.4645 (2.14); 3.4542 (2.10); 3.4421 (1.20); 3.3360 (129.83); 2.9322 (1.87); 2.9200 (3.20); 2.9081 (1.78); 2.5428 (14.60); 2.5214 (0.32); 2.5094 (7.43); 2.5064 (16.06); 2.5034 (22.23); 2.5004 (16.13); 2.4974 (7.56); 2.2605 (0.69); 2.2520 (16.00); -0.0002 (3.79)

8-21 4-(trifluormethyl)-phenyl CH2 CH2 - H CAS: 1325832-12-9

8-22 2-methyl-phenyl CH2 CH2 - H CAS: 1043269-68-6

[DMSO], Spektrometer: 601.6MHz 8.3712 (0.61); 7.6759 (1.40); 7.6732 (1.40); 6.7975 (3.13); 6.4963 (1.46); 6.4936 (1.46); 3.3334 (97.86); 3.2078 (0.43); 3.1980 (0.70); 3.1944 (0.55); 3.1888 (0.67); 3.1839 (0.54); 3.1797 (0.71); 3.1701 (0.49); 2.7659 (0.85); 2.7570 (0.61); 2.7518 (0.83); 2.7476 (0.62); 2.7383 (0.77); 2.5415 (5.51); 2.5081 (5.27); 2.5052 (1 1.49); 2.5022 (15.98); 2.4991 (1 1.53); 2.4962

8-23 2,4,6-trimethyl-phenyl CH2 CH2 H (5.33); 2.2934 (16.00); 2.1786 (5.69); -0.0002 (2.22)

8-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H CAS: 1036695-62-1

8-25 phenyl CH2 CH2 - H CAS: 1060941-00-5

8-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

8-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

8-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

8-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

8-30 4-chlor-phenyl 0 CH2 CH2 H CAS: 1325531-65-4

Verbindung Nr. 8-31 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,2551 (0,73); 8,2413 (1 ,4); 8,2273 (0,74); 7,6878 (3, 16); 7,6842 (3, 1 7); 7,5671 (2,97); 7,5607 (3, 19); 7,3816 (1 ,54); 7,3752 (1 ,45); 7,3594 (2,09); 7,353 (2,01 ); 7,24 (3,54); 7,2177 (2,63); 6,5049 (3,33); 6,5013 (3,32); 4, 1896 (2, 12); 4, 1 741 (4,72); 4, 1587 (2,35); 3,6071 (1 ,2); 3,5921 (3,32); 3,5772 (3,21 ); 3,562 (1 ,08); 3,334 (25,86); 2,5438 (1 3,28); 2,5267 (0,33); 2,5089 (10,22); 2,5046 (1 3,23); 2,5002 (10,08); 2,2826 (16); - 0,0002 (0,33)

8-31 2,4-dichlor-phenyl 0 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

8-32 4-chlor-phenyl CH2 CH2 CH2 H

8-33 4-chlor-phenyl NCH3 CH2 CH2 H

8-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

8-35 4-chlor-phenyl CH(OCH3) CH2 - H

8-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

8-37 2-thienyl CH2 CH2 - H CAS: 1015949-54-8

8-38 3-thienyl CH2 CH2 - H

8-39 2-furyl CH2 CH2 - H CAS: 1016026-83-7

8-40 3-furyl CH2 CH2 - H

8-41 phenyl CH2 CH2 CH(CH3) H

8-42 phenyl CH2 CH2 CH2 H

8-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

8-44 4-t-butyl-phenyl CH2 CH2 CH2 H

8-45 4-methyl-phenyl CH2 CH2 CH2 H

8-46 phenyl CH2 CH2 CH(CH2CH3) H

8-47 2-methoxy-phenyl CH2 CH2 CH2 H

8-48 2-methyl-phenyl CH2 CH2 CH2 H

8-49 3 -methyl-phenyl CH2 CH2 CH2 H

8-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 8-51 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,2012 (0,65); 8, 1868 (1 ,21 ); 8, 173 (0,66); 7,6566 (3); 7,653 (2,98); 7,3419 (0,33); 7,3249 (0,79); 7,3215 (0,73); 7,3042 (1 ,45); 7,2835 (0,94); 7,2666 (0,42); 7,0797 (2,03); 7,0598 (3,28); 7,0399 (1 ,68); 6,4825 (3,22); 6,4789 (3,24); 3,3291 (43,27); 3,2425 (1 ,02); 3,2257 (2, 16); 3,2081 (2, 18); 3, 1914 (1 ,07); 2,6559 (1 ,43); 2,6367 (2,4); 2,61 73 (1 ,57); 2,5071 (24,4); 2,5027 (32,29); 2,4983 (24,78); 2,2874 (0,37); 2,2627 (16); 1 ,7727 (0,55); 1 ,7532 (1 ,42); 1 ,7349 (2,05);

8-51 2,6-difluor-phenyl CH2 CH2 CH2 H 1 ,7162 (1 ,33); 1 ,6975 (0,48); -0,0002 (0,34)

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

8-52 4-chlor-phenyl CH2 CH2 CH2 H

8-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

8-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

8-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

8-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

8-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

8-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

8-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

8-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

8-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

8-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

8-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

8-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

8-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

8-66 4-phenoxy-phenyl CH2 CH2 CH2 H

8-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

8-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

8-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

8-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

8-71 4-methoxy-phenyl CH2 CH2 CH2 H

8-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

8-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

8-74 4-fluor-phenyl CH2 CH2 CH2 H

8-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

8-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

8-77 2-chlor-phenyl CH2 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

8-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Verbindung Nr. 8-79, Solvent: [DMSO], Spektrometer: 399.95MHz

8,221 (0,63); 8,2071 (1 ,15); 8,1929 (0,64); 7,6601 (2,99); 7,6565 (3,01 ); 7,3135 (1 ,85); 7,3107 (1 ,85); 7,3007 (2,05); 7,2979 (1 ,95); 6,9452 (1 ,53); 6,9367 (2,1 ); 6,9325 (1 ,56); 6,924 (1 ,94); 6,8841 (2,07); 6,8822 (2,07); 6,876 (1 ,67); 6,487

(3.15) ; 6,4834 (3,17); 3,3298 (24,93); 3,2682

(1 .16) ; 3,2515 (2,62); 3,235 (2,63); 3,2183 (1 ,23); 2,8303 (1 ,94); 2,81 1 1 (3,31 ); 2,792 (2, 12); 2,5418 (1 ,02); 2,5245 (0,38); 2,5068 (13,21 ); 2,5024 (17,54); 2,498 (13,39); 2,2729 (16); 1 ,8665 (0,62); 1 ,848 (1 ,79); 1 ,8294 (2,39); 1 ,81 13 (1 ,72); 1 ,7928

8-79 2-thienyl CH2 CH2 CH2 H (0,57)

Verbindung Nr. 8-80, Solvent: [DMSO], Spektrometer: 601.6MHz

8,2854 (0,55); 8,2761 (1 ,03); 8,2669 (0,54); 7,6694 (2,74); 7,6667 (2,72); 7,3628 (3,72); 7,3602 (3,83); 6,8983 (2,61 ); 6,8971 (2,5); 6,896 (2,67); 6,492 (2,8); 6,4894 (2,87); 3,4515 (1 ,07); 3,4397 (2,48); 3,4298 (2,5); 3,4181 (1 , 16); 3,3249 (297,13); 3,0042 (1 ,78); 2,9924 (3,36); 2,981 1 (1 ,58); 2,6529 (0,53); 2,6162 (0,46); 2,6131 (0,62); 2,6101 (0,45); 2,5408 (159,37); 2,5224 (1 ,46); 2,5193 (1 ,94); 2,5162 (2,27); 2,5074 (35,62); 2,5044 (73,23); 2,5014 (100,26); 2,4983 (73,35); 2,4953 (34,47); 2,4244 (0,53); 2,3886 (0,45); 2,3856 (0,62); 2,3825 (0,45); 2,2685 (16);

8-80 4-chlor-2-thienyl CH2 CH2 H 2,0736 (0,38); -0,0002 (6,04)

Verbindung Nr. 8-81 , Solvent: [DMSO], Spektrometer: 399.95MHz

8,2378 (0,68); 8,2238 (1 ,29); 8,2099 (0,68); 7,6642 (3,05); 7,6607 (2,89); 7,1804 (0,49); 7, 1717 (4,21 ); 7,1665 (1 ,43); 7,149 (4,63); 7,1402 (0,51 ); 6,774 (0,59); 6,7656 (4,48); 6,7429 (3,98); 6,4866 (3,24); 6,4831 (3,01 ); 3,4418 (1 ,08); 3,4248 (2,45); 3,4071 (2,29); 3,3521 (1 ,68); 3,3299 (50,37); 3,3052 (0,87); 2,9004 (16); 2,5418 (1 1 ,39); 2,5068 (22,85); 2,5024 (28,29);

8-81 4-chlor-phenyl N(CH3) CH2 CH2 H 2,498 (20,57); 2,2758 (15,31 ); -0,0002 (3,19)

Tabelle 9

Verbindungen der Formel 1-9

Physikalische Daten: Ή-NMR, 0 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

9-1 3 -methyl-2-thienyl CH2 CH2 - H

Verbindung Nr.9-2, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4664 (2,17); 8,4522 (4,21); 8,438 (2,2); 7,8913 (15,07); 7,8865 (15,06); 7,5619 (11,18); 7,5566 (11,52); 7,4291 (7,37); 7,4084 (14,84); 7,3742 (9,98); 7,3689 (9,31); 7,3536 (4,8); 7,3482 (4,73); 6,84 (16); 6,8352 (15,71); 3,516 (0,61); 3,3411 (75,64); 3,2676 (3,72); 3,2505 (8,4); 3,2349 (8,41); 3,2177 (3,87); 2,7236 (6,71); 2,7051 (8,66); 2,6851 (7,33); 2,5465 (32,88); 2,5296 (0,71); 2,5248 (1,1); 2,5163 (14,33); 2,5118 (28,9); 2,5072 (38,46); 2,5026 (28,04); 2,498 (13,4); 1,8153(1,91); 1,7967 (5,02); 1,7783 (6,69); 1,7599 (4,75); 1,7416(1,7);

9-2 2,4-dichlor-phenyl CH2 CH2 CH2 H -0,0002 (3,86)

Verbindung Nr.9-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4476 (1,57); 8,4333 (2,98); 8,4191 (1,54); 7,8832 (10,65); 7,8784 (10,58); 7,3633 (1,16); 7,3569 (10,15); 7,3523 (3,58); 7,3409 (4,33); 7,336 (16); 7,3299 (2,03); 7,2686 (2,05); 7,2627 (14,04); 7,2462 (3,26); 7,2417 (8,9); 6,8358 (11,21); 6,831 (11); 3,4432 (2,92); 3,4261

9-3 4-chlor-phenyl CH2 CH2 H (5,63); 3,4106 (5,3); 3,4074 (5,52); 3,3919

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

(3,26); 3,3341 (429,8); 3,2919 (0,4); 2,8278 (5,24); 2,8092 (8,27); 2,7912 (4,66); 2,7119(1,53); 2,6761 (0,81); 2,6715 (1,1); 2,6671 (0,81); 2,5727 (0,63); 2,5418 (347,78); 2,5249 (3,65); 2,5199 (5,37); 2,5114 (62,94); 2,507 (126,53); 2,5025 (166,36); 2,498 (120,67); 2,4936 (58,56); 2,3682 (1,56); 2,3381 (0,38); 2,3337 (0,79); 2,3292 (1,07); 2,3248 (0,78); 2,0746 (0,75); 0,008 (0,53); - 0,0002 (15,19); -0,0086 (0,43)

Verbindung Nr.9-4, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5057 (1,91); 8,4914 (3,79); 8,477 (1,92); 7,883 (15,24); 7,8782 (15,44); 7,5843 (8,45); 7,58 (9,26); 7,3849 (1,98); 7,3803

(1.42) ; 7,3642 (12,12); 7,3595 (14,17); 7,3558 (16); 7,3354 (2,11); 6,8351 (15,97); 6,8303 (15,9); 3,4689 (3,33); 3,4519 (7,31); 3,4362 (7,18); 3,4186 (4,05); 3,3455 (1196,3); 3,2764 (0,55); 3,2619 (0,48); 2,947 (6,38); 2,929 (10,97); 2,9114 (5,59); 2,7125 (1,77); 2,6815 (0,6); 2,6769 (1,19); 2,6723 (1,68); 2,6677

(1 ,25); 2,6632 (0,62); 2,5942 (0,33); 2,5826 (0,51); 2,5426 (476,9); 2,5312

(2.43) ; 2,5304 (2,5); 2,5255 (5,45); 2,5208 (8,28); 2,5123 (92,1); 2,5078 (186,91); 2,5032 (246,51); 2,4986 (177,91); 2,4941 (84,91); 2,3687 (1,75); 2,3392 (0,53); 2,3345 (1,13); 2,3299 (1,58); 2,3254 (1,14); 2,321 (0,55); 2,0744 (1,1); 1,2348 (0,37); 0,0081 (0,87); -0,0001 (24,05); -

9-4 2,4-dichlor-phenyl CH2 CH2 H 0,0084 (0,68)

9-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

9-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

9-7 4-chlor-phenyl CH(CH3) CH2 - H

Verbindung Nr.9-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4383 (1 ,22); 8,4239 (2,52); 8,4093 (1 ,3);

9-8 2,4-dichlor-phenyl CH(CH3) CH2 H 7,8649 (9,5); 7,8602 (9,81); 7,5579 (7,09);

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

7,5527 (7,65); 7,4577 (3,26); 7,4365 (9,51); 7,4185 (6,03); 7,4132 (5,54); 7,3973 (2,05); 7,3921 (2,08); 6,8223 (9,99); 6,8175 (10,05); 3,5571 (0,95); 3,5389 (2,05); 3,5212 (2,39); 3,5039 (1,42); 3,4866 (0,38); 3,426 (4,8); 3,4108 (6,07); 3,393 (3,53); 3,3311 (719,9); 2,7113 (1,55); 2,6801 (0,71); 2,6757 (1 ,45); 2,6711 (1 ,99); 2,6666 (1 ,49); 2,662 (0,75); 2,5415 (416,13); 2,5244 (6,83); 2,5196 (10,09); 2,5111 (110,28); 2,5066 (222,85); 2,502 (294,79); 2,4974 (212,26); 2,4929 (102,2); 2,3675 (1,53); 2,338 (0,64); 2,3333 (1,39); 2,3287 (1,9); 2,3242 (1 ,38); 2,3197 (0,65); 2,0746 (1 ,36); 1 ,235 (0,4); 1,1833 (16); 1,1661 (15,73); 0,008 (0,94); -0,0002 (24,94); -0,0084 (0,75)

Verbindung Nr.9-9, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2709 (2,54); 8,2499 (2,53); 7,8735 (9,69); 7,8687 (9,65); 7,3359 (0,97); 7,3298 (8,1); 7,3249 (2,87); 7,3137 (3,72); 7,3086 (14,16); 7,3027 (1,8); 7,2562 (1,96); 7,2504(12,3); 7,2455 (3,42); 7,2339 (2,64); 7,2292 (7,08); 6,8197 (10,3); 6,8149 (10,08); 4,1826 (0,62); 4,1662 (1,14); 4,1622 (1,32); 4,1459 (1,93); 4,1294 (1,37); 4,1254 (1,12); 4,1092 (0,64); 3,3915 (0,36); 3,3783 (0,52); 3,3335 (390,11); 3,3041 (0,63); 2,8867 (1,85); 2,8664 (1,81); 2,8531 (2,77); 2,8328 (2,68); 2,7432 (2,76); 2,7277 (2,81); 2,7108 (2,57); 2,694 (1,77); 2,6805 (0,41); 2,676 (0,76); 2,6715 (1,01); 2,6669 (0,74); 2,6625 (0,34); 2,5797 (0,38); 2,5761 (0,44); 2,5661 (0,91); 2,5418 (336,04); 2,5249 (3,4); 2,5199 (5,02); 2,5114 (55,84); 2,507 (112,23); 2,5024 (147,1); 2,4978 (105,38); 2,4933 (49,81); 2,3678 (1,22); 2,3337 (0,68); 2,3291 (0,94); 2,3245 (0,65); 2,0747 (0,75); 1,1413 (16); 1,1248 (15,82); 0,008

9-9 4-chlor-phenyl CH2 CH(CH3) H (0,51); -0,0002 (15,04); -0,0085 (0,45)

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

Verbindung Nr. 9-10, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3289 (2,32); 8,307 (2,34); 7,88 (8,38); 7,8752 (8,32); 7,561 (5,66); 7,3598 (0,58); 7,3405 (16); 7,3365 (8,81 ); 7,3156 (0,51 ); 6,8195 (8,93); 6,8148 (8,69); 4,3154 (0,51 ); 4,2994 (0,95); 4,2948 (1 ,05); 4,2785 (1 ,56); 4,2619 (1 , 14); 4,2581 (0,91 ); 4,2415 (0,52); 3,3296 (152,91 ); 2,9677 (0,81 ); 2,9473 (0,7); 2,9334 (3,42); 2,9171 (4,18); 2,9132 (4,26); 2,902 (3,69); 2,8831 (0,87); 2,8677 (0,63); 2,6761 (0,44); 2,6715 (0,6); 2,6671 (0,45); 2,5418 (27,6); 2,5249 (2,15); 2,52 (3,35); 2,51 16 (36,55); 2,5071 (72,87); 2,5025 (95,04); 2,498 (67,94); 2,4935 (32,18); 2,3339 (0,43); 2,3292 (0,6); 2,3248 (0,43); 2,0753 (0,58); 1 ,1815 (13, 1 1 ); 1 ,1649 (12,95); -

9-10 2,4-dichlor-phenyl CH2 CH(CH3) H 0,0002 (9,58)

Verbindung Nr. 9-1 1 , Solvent: [DMSO], Spektrometer: 399.95MHz

7,9517 (0,35); 7,9364 (0,69); 7,9209 (0,36); 7,8692 (2,81 ); 7,8644 (2,83); 7,4361 (2,06); 7,4308 (0,79); 7,4197 (1 ,03); 7,4142 (4,3); 7,408 (0,63); 7,3785 (0,6); 7,3723 (4,38); 7,3669 (1 ,05); 7,3556 (0,74); 7,3504 (2,07); 6,8234 (2,96); 6,8186 (2,93); 3,4123 (2,77); 3,3962 (2,74); 3,3287 (66,42); 2,5414 (8,25); 2,5244 (0,87); 2,5197 (1 ,35); 2,51 12 (14,71 ); 2,5067 (29,55); 2,5021 (38,8); 2,4975 (28,08); 2,4931 (13,5); 1 ,2687

9-11 4-chlor-phenyl C(CH3)2 CH2 H (16); -0,0002 (3,64)

Verbindung Nr. 9-12, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0394 (0,42); 8,0236 (0,83); 8,0079 (0,41 ); 7,8579 (2,66); 7,8532 (2,64); 7,5397 (2,36); 7,5339 (2,47); 7,4674 (1 ,48); 7,4457 (2,27); 7,3728 (1 ,51 ); 7,367 (1 ,41 ); 7,3513 (0,98); 7,3455 (0,93); 6,8124 (2,75); 6,8077 (2,68); 3,7514 (2,8); 3,7352 (2,76); 3,3316 (61 ,88); 2,5422

9-12 2,4-dichlor-phenyl C(CH3)2 CH2 H (46,1 1 ); 2,5244 (0,68); 2,51 13 (1 1 ,34);

Physikalische Daten: ¹ H-N R, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

2,6672 (0,98); 2,6625 (0,49); 2,5421 (435,01 ); 2,5251 (4,29); 2,5203 (6,45); 2,51 18 (72,78); 2,5073 (146,59); 2,5027 (192,43); 2,4981 (137,67); 2,4936 (65, 14); 2,4647 (0,44); 2,3682 (1 ,66); 2,3383 (0,42); 2,334 (0,88); 2,3294 (1 ,2); 2,3248 (0,86); 2,3203 (0,41 ); 2,0751 (0,95); 1 ,2343 (0,33); 0,008 (0,64); -0,0002 (19,48); -0,0085 (0,55)

Verbindung Nr. 9-15, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4586 (1 ,5); 8,4444 (2,86); 8,4305 (1 ,47); 7,8902 (9,3); 7,8855 (9,22); 7,4381 (3,79); 7,4335 (7,33); 7,4288 (4,2); 7,3104 (16); 7,3058 (14,94); 6,8386 (9,68); 6,8338 (9,46); 3,4749 (2,45); 3,4577 (6,05); 3,4425 (6,16); 3,4253 (2,74); 3,3931 (0,39); 3,3857 (0,43); 3,3345 (369,91 ); 3,2875 (0,41 ); 2,8585 (4,53); 2,841 (8,8); 2,8235 (4,05); 2,71 17 (1 , 19); 2,6761 (0,76); 2,6715 (0,97); 2,667 (0,72); 2,6627 (0,38); 2,5849 (0,34); 2,542 (280,12); 2,5248 (3,63); 2,51 14 (56,72); 2,507 (1 1 1 ,12); 2,5025 (144,2); 2,4979 (104,8); 2,4935 (51 ,15); 2,3679 (1 ,2); 2,338 (0,35); 2,3337 (0,71 ); 2,3292 (0,95); 2,3248 (0,68); 2,0748 (0,58); 0,008 (0,46); -

9-15 3,5- dichlor-pheny 1 CH2 CH2 H 0,0002 (1 1 ,7); -0,0084 (0,43)

Verbindung Nr. 9-16, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4568 (2); 8,4431 (3,7); 8,4294 (1 ,96); 7,8873 (13,82); 7,8825 (14,02); 7,3569 (0,48); 7,343 (3,53); 7,3359 (0,88); 7,3235 (8,94); 7,3048 (16); 7,2775 (4,67); 7,2743 (6,57); 7,2689 (3,75); 7,2625 (0,89); 7,2577 (2,83); 7,2547 (2,52); 7,2528 (2,64); 7,2497 (1 ,93); 7,2414 (0,37); 7,205 (6,54); 7,1864 (4,31 ); 6,8376 (14,52); 6,8328 (14,26); 3,4619 (3,76); 3,4447 (7,43); 3,4294 (7,12); 3,4265 (7,24); 3,4109 (4,42); 3,3914 (0,71 ); 3,3825 (0,74); 3,3337 (631 ,19); 3,3035 (0,95);

9-16 3-chlor-phenyl CH2 CH2 H 3,2912 (0,5); 2,8484 (6,66); 2,8299 (1 1 );

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

2,812 (6,09); 2,71 16 (2,09); 2,6804 (0,6); 2,6759 (1 ,18); 2,6714 (1 ,59); 2,667 (1 ,22); 2,6622 (0,62); 2,5927 (0,37); 2,5418 (489,07); 2,5247 (5,31 ); 2,5197 (7,89); 2,51 13 (88,21 ); 2,5069 (176,46); 2,5023 (231 ,72); 2,4978 (167,78); 2,4933 (80,85); 2,3678 (2,05); 2,3381 (0,51 ); 2,3337 (1 ,07); 2,3291 (1 ,48); 2,3246 (1 ,08); 2,3204 (0,5); 2,0747 (1 ,09); 1 ,2353 (0,35); 0,0081 (0,66); -0,0002 (19); -0,0083 (0,59)

Verbindung Nr. 9-17, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5015 (2,01 ); 8,4875 (3,76); 8,4731 (1 ,98); 7,8846 (15,25); 7,8798 (15,41); 7,3218 (2,07); 7,3178 (2,63); 7,3032 (4,2); 7,2986 (5,86); 7,2912 (1 ,72); 7,2781 (4,94); 7,2626 (3,21 ); 7,2569 (4,02); 7,2524 (2,13); 7,2432 (2,29); 7,2387 (1 ,78); 7,1717 (4,2); 7, 1498 (8,85); 7,1334 (7,61 ); 7,1303 (7,46); 7,1253 (2,95); 7,1 15 (3,17); 7,1 12 (2,74); 6,836 (15,97); 6,8312 (16); 3,4541 (3,8); 3,4374 (7, 19); 3,4212 (6,64); 3,4178 (7,33); 3,4025 (4,32); 3,3342 (625,22); 3,2939 (0,64); 3,2701 (0,34); 2,8724 (5,93); 2,8538 (9,52); 2,8356 (5,19); 2,71 17 (2, 13); 2,6805 (0,56); 2,676 (1 ,14); 2,6715 (1 ,55); 2,6669 (1 ,14); 2,6623 (0,59); 2,5919 (0,32); 2,5904 (0,37); 2,5897 (0,37); 2,589 (0,38); 2,5882 (0,38); 2,5875 (0,4); 2,5868 (0,41 ); 2,586 (0,43); 2,5846 (0,48); 2,5839 (0,48); 2,5831 (0,47); 2,5809 (0,61 ); 2,5794 (0,68); 2,5787 (0,7); 2,578 (0,7); 2,5773 (0,71 ); 2,5765 (0,71 ); 2,5758 (0,71 ); 2,575 (0,73); 2,5736 (0,83); 2,5728 (0,86); 2,5721 (0,9); 2,5713 (0,96); 2,5706 (1); 2,5699 (1 ,03); 2,5691 (1 ,08); 2,5632

(2.06) ; 2,5625 (2,13); 2,5418 (539,77); 2,5248 (5,45); 2,5197 (7,8); 2,51 14 (85,7); 2,5069 (172,68); 2,5024 (227,41 ); 2,4978 (165,24); 2,4933 (79,96); 2,4533 (0,41 ); 2,3678 (2,12); 2,3381 (0,53); 2,3337

9-17 2-fluor-phenyl CH2 CH2 H (1 .07) ; 2,3291 (1 ,47); 2,3245 (1 ,07);

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

2,0747 (1 ,21 ); 1 ,2347 (0,36); 0,008 (0,7); - 0,0002 (19,73); -0,0085 (0,61 )

Verbindung Nr. 9-18, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5562 (2,09); 8,5417 (4,02); 8,527 (2,04); 7,8822 (15,22); 7,8775 (15,1 1 ); 7,3578 (1 ,21 ); 7,3409 (2,69); 7,3369 (2,43); 7,3201 (5,16); 7,303 (2,56); 7,2992 (3,32); 7,2824 (1 ,54); 7,096 (0,71 ); 7,0916 (1 ,01 ); 7,0794 (7,23); 7,0595 (1 1 ,38); 7,0483 (1 ,4); 7,0395 (6); 7,0269 (0,76); 6,8335 (16); 6,8287 (15,61 ); 3,4179 (3,76); 3,4014 (8,33); 3,3832 (8,36); 3,3671 (5,35); 3,3349 (585,57); 3,2812 (0,32); 2,8879 (5,34); 2,8699 (9,42); 2,8522 (4,73); 2,712 (2,13); 2,6808 (0,55); 2,6762 (1 ,07); 2,6717 (1 ,4); 2,6672 (1 ,07); 2,6627 (0,54); 2,588 (0,44); 2,542 (493); 2,5249 (4,6); 2,5201 (6,98); 2,51 17 (78,39); 2,5072 (157,19); 2,5026 (205,6); 2,4981 (147,59); 2,4936 (70,16); 2,3682 (2,04); 2,3383 (0,44); 2,3339 (0,93); 2,3294 (1 ,3); 2,3248 (0,92); 2,3203 (0,41 ); 2,0748 (1 ,01 ); 0,008 (0,67); -0,0002 (19,34); -

9-18 2,6-difluor-phenyl CH2 CH2 H 0,0085 (0,55)

Verbindung Nr. 9-19, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6015 (1 ,33); 8,5872 (2,57); 8,5723 (1 ,29); 7,8872 (9,54); 7,8825 (9,59); 7,4606 (1 1 ,42); 7,4405 (16); 7,3004 (5,5); 7,2813 (5,18); 7,2792 (4,96); 7,2601 (3,53); 6,8351 (10,07); 6,8303 (9,96); 3,4497 (2,02); 3,4334 (4,64); 3,4285 (2,89); 3,4175 (4,01 ); 3,4133 (4,62); 3,3984 (2,6); 3,3325 (381 ,04); 3,1556 (4,55); 3,1361 (6,36); 3, 1 191 (3,55); 2,71 16 (1 ,08); 2,6804 (0,35); 2,676 (0,73); 2,6715 (1 ,01 ); 2,6669 (0,73); 2,6626 (0,37); 2,5764 (0,42); 2,5418 (296); 2,5249 (3,38); 2,52 (5,06); 2,51 14 (57, 1 1 ); 2,507 (1 15,45); 2,5024 (152,39); 2,4978 (1 10,49); 2,4933 (53,18); 2,3678 (1 ,1 1 );

9-19 2,6-dichlor-phenyl CH2 CH2 H 2,3381 (0,34); 2,3337 (0,71 ); 2,3291

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

Spektrometer: 399.95MHz

8,4036 (0,5); 8,3898 (0,96); 8,3756 (0,48); 7,8864 (3,18); 7,8817 (3, 15); 6,8699 (2,07); 6,8495 (2,8); 6,8384 (3,38); 6,8337 (3,28); 6,813 (2,21 ); 6,8082 (2,44); 6,7402 (1 ,39); 6,7355 (1 ,24); 6,7199 (1 ,03); 6,7152 (0,94); 3,7217 (16); 3,7097 (15,93); 3,4305 (0,79); 3,4143 (1 ,52); 3,3972 (1 ,41 ); 3,3939 (1 ,54); 3,3786 (0,95); 3,3692 (0,36); 3,3344 (128,3); 2,7616 (1 ,47); 2,7422 (2,09); 2,7244 (1 ,3); 2,71 17 (0,5); 2,5417 (105,77); 2,5245 (1 ,04); 2,51 13 (18,38); 2,5068 (36,29); 2,5023 (47,29); 2,4978 (34,09); 2,4934 (16,38); 2,3679 (0,48); -0,0002 (3,92)

Verbindung Nr. 9-25, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4513 (1 ,78); 8,4374 (3,32); 8,4233 (1 ,8); 7,8857 (15,05); 7,8809 (15,27); 7,3174 (4,61 ); 7,3135 (2,02); 7,299 (1 1 ,17); 7,2855 (3,59); 7,2809 (1 1 ,21 ); 7,2413 (8,94); 7,2376 (14,49); 7,2203 (1 1 ,08); 7,207 (2,6); 7,2019 (6,15); 7,1964 (1 ,62); 7, 1876 (1 ,43); 7,184 (2,24); 7,1805 (1 ,18); 6,8376 (16); 6,8328 (15,93); 3,4499

(4.03) ; 3,4345 (6,67); 3,4316 (6,04); 3,4277 (4,3); 3,4167 (5,87); 3,4125 (7,32); 3,3976 (4,64); 3,3351 (608,2); 3,2783 (0,35); 3,2713 (0,35); 2,8322 (6,91 ); 2,8125 (8,97); 2,7945 (6,16); 2,71 16

(2.04) ; 2,6804 (0,56); 2,6759 (1 ,14); 2,6713 (1 ,55); 2,6668 (1 , 17); 2,6622 (0,56); 2,5943 (0,4); 2,5842 (0,43); 2,5416 (553,82); 2,5247 (5,07); 2,5199 (7,8); 2,51 13 (85,67); 2,5068 (174,07); 2,5022 (229,82); 2,4976 (165,61 ); 2,4931 (78,84); 2,3678 (2,01 ); 2,3382 (0,53); 2,3336

(1 ,08); 2,329 (1 ,48); 2,3243 (1 ,09); 2,32 (0,53); 2,0744 (1 ,24); 1 ,2347 (0,33); 0,008

9-25 phenyl CH2 CH2 H (0,83); -0,0002 (24,03); -0,0085 (0,66)

9-26 4-chlor-phenyl C(CH2-CH2) CH2 H

9-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 H

Physikalische Daten: ¹ H-NMR, 6 Ippm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

9-28 4-chlor-phenyl CH2 C(CH2-CH2) H

9-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) H

9-30 4-chlor-phenyl O CH2 CH2 H

Verbindung Nr.9-31, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5029 (2,45); 8,4891 (4,79); 8,4753 (2,53); 7,9192 (13,04); 7,9145 (13,54); 7,567 (9,73); 7,5606 (10,61); 7,384 (5,33); 7,3775 (5,12); 7,3618 (7,19); 7,3554 (7,06); 7,2385 (12,33); 7,2162 (9,27); 6,8616 (13,39); 6,8568 (13,7); 4,2028 (7,13); 4,1876 (16); 4,1725 (7,94); 3,6229 (3,98); 3,6081 (11,19); 3,5934 (10,88); 3,5784 (3,68); 3,3342 (50,52); 2,5453 (47,37); 2,5283 (0,77); 2,5104 (25,95); 2,5059 (34,95); 2,5015 (26,98); -0,0002

9-31 2,4-dichlor-phenyl O CH2 CH2 H (1.22)

Verbindung Nr.9-32, Solvent: [DMSO], Spektrometer: 399.95MHz

8,423 (1,43); 8,4087 (2,66); 8,3948 (1,37); 7,8835 (11,11); 7,8788 (11,28); 7,3448

(1.08) ; 7,3386 (8,69); 7,3338 (3,46); 7,3226 (4,14); 7,3175 (16); 7,3117 (2,42); 7,2683 (2,14); 7,2626 (13,33); 7,2578

(4.09) ; 7,2462 (2,84); 7,2415 (7,72); 6,8357 (11,61); 6,8309 (11,57); 3,3996 (0,35); 3,3342 (448,7); 3,3001 (0,49); 3,2271 (2,59); 3,21 (5,56); 3,1943 (5,43); 3,1773 (2,62); 2,7114 (1,42); 2,6802 (0,4); 2,6759 (0,81); 2,6714 (1,13); 2,6669 (0,84); 2,6625 (0,43); 2,6131 (4,49); 2,5944 (6,82); 2,5749 (5,33); 2,5668

(1 ,31 ); 2,5653 (1 ,27); 2,5646 (1 ,26); 2,5608 (1,68); 2,5419 (360,69); 2,529 (2,13); 2,5246 (3,78); 2,5113 (61,29); 2,5069 (124,75); 2,5023 (165,59); 2,4978 (121,75); 2,4932 (59,55); 2,3676 (1,4); 2,3382 (0,37); 2,3336 (0,77); 2,3291 (1,06); 2,3244 (0,78); 2,3201 (0,38); 2,0747 (0,88); 1,8153 (1,33); 1,7965

9-32 4-chlor-phenyl CH2 CH2 CH2 H (3,66); 1,7782 (4,9); 1,7598 (3,42); 1,7415

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

9-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 9-51 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,443 (2,14); 8,4285 (3,98); 8,4142 (2,08); 7,8867 (15,33); 7,882 (15,59); 7,345 (1 ,2); 7,3282 (2,66); 7,3241 (2,47); 7,3072 (5,08); 7,2899 (2,53); 7,2864 (3,35); 7,2696 (1 ,5); 7,0989 (0,75); 7,0944 (1 ,09); 7,0818 (6,83); 7,0617 (1 1 ,33); 7,0497 (1 ,52); 7,0416 (5,76); 7,0283 (0,76); 6,837 (15,95); 6,8322 (16); 3,4158 (0,48); 3,4042 (0,68); 3,3356 (798,74); 3,289 (0,81 ); 3,2517 (3,51 ); 3,2348 (7,08); 3,2173 (7,01 ); 3,2008 (3,5); 2,7124 (2, 13); 2,6766 (1 ,66); 2,6664 (5,52); 2,6464 (8,01 ); 2,627 (5,3); 2,5427 (499,5); 2,5255 (7,14); 2,5121 (91 ,75); 2,5078 (181 ,6); 2,5032 (238,19); 2,4987 (175,98); 2,4943 (87,47); 2,4471 (0,45); 2,3686 (2,05); 2,3389 (0,57); 2,3345 (1 ,13); 2,3299 (1 ,55); 2,3254 (1 ,16); 2,0754 (1 ,15); 1 ,7839 (1 ,84); 1 ,7646 (4,7); 1 ,7463 (6,69); 1 ,7273 (4,26); 1 ,7089 (1 ,55); 1 ,2349 (0,37); 0,0085 (0,81 ); 0,0004 (20,1 1 ); - 0,0078 (0,73)

9-51 2,6-difluor-phenyl CH2 CH2 CH2 H

9-52 4-chlor-phenyl CH2 CH2 CH2 H

9-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

9-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

9-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

9-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

9-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

9-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

9-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

9-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

9-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

9-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

9-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

9-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

9-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

9-66 4-phenoxy-phenyl CH2 CH2 CH2 H

9-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

9-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

9-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

9-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

9-71 4-methoxy-phenyl CH2 CH2 CH2 H

9-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

9-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

9-74 4-fluor-phenyl CH2 CH2 CH2 H

9-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

9-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

9-77 2-chlor-phenyl CH2 CH2 CH2 H

9-78 4-chlor-phenyl CH2 CH(CH3) cyclopropyl

Verbindung Nr. 9-79, Solvent: [DMSO], Spektrometer: 399.95MHz 8,4599 (2,61 ); 8,4461 (4,83); 8,4323 (2,69); 7,8913 (15,42); 7,8865 (15,68); 7,3171 (7,72); 7,3143 (7,67); 7,3044 (8,56); 7,3015 (8,12); 6,9479 (6,27);

6,9393 (8,65); 6,9352 (6,4); 6,9266 (8,01 ); 6,8879 (8,55); 6,8859 (8,57); 6,8797 (6,9); 6,8409 (16); 6,8361 (15,96); 3,3334 (63,52); 3,2786 (4,65); 3,2618 (10,55); 3,2457 (10,61 ); 3,2289 (4,88); 2,8423 (7,82); 2,8231 (13,43); 2,8041 (8,47); 2,5431 (10,08); 2,526 (0,99); 2,5082 (33,08); 2,5038 (43,76); 2,4994 (33,35);

9-79 2-thienyl CH2 CH2 CH2 H 1 ,8771 (2,49); 1 ,8587 (7,26); 1 ,8402

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

(9,71); 1,822 (6,95); 1,8036 (2,23); - 0,0002 (0,41)

Verbindung Nr.9-80, Solvent: [DMSO], Spektrometer: 601.6MHz

8,528 (1,75); 8,5186 (3,38); 8,5091 (1,76); 7,9005 (15,38); 7,8973 (15,32); 7,3685 (13,84); 7,366 (14,11); 6,9083 (8,96); 6,9071 (7,97); 6,9059 (8,74); 6,847 (15,57); 6,8438 (16); 3,4617 (3,43); 3,4499 (8,05); 3,4402 (8,31); 3,4285 (3,81); 3,4089 (0,45); 3,3255 (899,24); 3,3034 (0,66); 3,0139 (5,58); 3,0021 (10,72); 2,9909 (5,08); 2,6532 (1 ,68); 2,6194 (0,56); 2,6164 (1,25); 2,6133 (1 ,73); 2,6103 (1 ,26); 2,6073 (0,59); 2,5596 (0,36); 2,541 (531,04); 2,5323 (1,2); 2,5227 (3,3); 2,5195 (4,08); 2,5164 (3,99); 2,5077 (92,61); 2,5046 (197,84); 2,5016 (274,23); 2,4985 (197,76); 2,4955 (92,09); 2,4249 (1,7); 2,3919 (0,53); 2,3888 (1 ,21 ); 2,3858 (1 ,68); 2,3827 (1,18); 2,3797 (0,53); 2,0738 (1 ,5); 1 ,9005 (0,51); 0,0052 (0,57); -0,0002 (18,84); -

9-80 4-chlor-2-thienyl CH2 CH2 H 0,0057 (0,59)

Verbindung Nr.9-81, Solvent: [DMSO], Spektrometer:

399.95MHz

8,4449 (1,85); 8,4308 (3,49); 8,4168(1,78); 7,8832(12,49); 7,8784 (12,44); 7,4943 (1,73); 7,4879 (13,75); 7,4833 (4,7); 7,4717 (4,89); 7,4671 (16);

7,4609 (2,07); 7,2044(13,74); 7,1835(11,82); 6,8349(13,52); 6,8301 (13,28); 4,0557 (0,51); 4,038 (1,57); 4,0202 (1,59); 4,0023 (0,53); 3,4412 (3,09);

9-81 4-brom-phenyl CH2 CH2 H 3,4242 (6,16); 3,4085 (5,83);

Tabelle 10

Verbindungen der Formel 1-10

1-10

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

10-1 3 -methyl-2-thienyl CH2 CH2 - H

10-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

10-3 4-chlor-phenyl CH2 CH2 - H

10-4 2,4-dichlor-phenyl CH2 CH2 - H

10-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

10-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

10-7 4-chlor-phenyl CH(CH3) CH2 - H

10-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

10-9 4-chlor-phenyl CH2 CH(CH3) - H

10-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

10-11 4-chlor-phenyl C(CH3)2 CH2 - H

10-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H

10-13 2-chlor-phenyl CH2 CH2 - H

10-14 3 ,4-dichlor-phenyl CH2 CH2 - H

10-15 3,5- dichlor-pheny 1 CH2 CH2 - H

10-16 3-chlor-phenyl CH2 CH2 - H

10-17 2-fluor-phenyl CH2 CH2 - H

10-18 2,6-difluor-phenyl CH2 CH2 - H

10-19 2,6-dichlor-phenyl CH2 CH2 - H

10-20 3 -(trifluormethyl)-phenyl CH2 CH2 - H

10-21 4-(trifluormethyl)-phenyl CH2 CH2 - H

10-22 2-methyl-phenyl CH2 CH2 - H

10-23 2,4,6-trimethyl-phenyl CH2 CH2 - H

10-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H

10-25 phenyl CH2 CH2 - H

10-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

10-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

10-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

10-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

10-30 4-chlor-phenyl 0 CH2 CH2 H

10-31 2,4-dichlor-phenyl 0 CH2 CH2 H

10-32 4-chlor-phenyl CH2 CH2 CH2 H

10-33 4-chlor-phenyl NCH3 CH2 CH2 H

10-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

10-35 4-chlor-phenyl CH(OCH3) CH2 - H

10-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

10-37 2-thienyl CH2 CH2 - H

10-38 3-thienyl CH2 CH2 - H

10-39 2-furyl CH2 CH2 - H

10-40 3-furyl CH2 CH2 - H

10-41 phenyl CH2 CH2 CH(CH3) H

10-42 phenyl CH2 CH2 CH2 H

10-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

10-44 4-t-butyl-phenyl CH2 CH2 CH2 H

10-45 4-methyl-phenyl CH2 CH2 CH2 H

10-46 phenyl CH2 CH2 CH(CH2CH3) H

10-47 2-methoxy-phenyl CH2 CH2 CH2 H

10-48 2-methyl-phenyl CH2 CH2 CH2 H

10-49 3 -methyl-phenyl CH2 CH2 CH2 H

10-50 3-chlor-phenyl CH2 CH2 CH2 H

10-51 2,6-difluor-phenyl CH2 CH2 CH2 H

10-52 4-chlor-phenyl CH2 CH2 CH2 H

10-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

10-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

10-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

10-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

10-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

10-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

10-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

10-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

10-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

10-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

10-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

10-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS-

Bsp.-Nr. X L ¹ L ² L ³ Y bzw. Patent-Nr.

10-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

10-66 4-phenoxy-phenyl CH2 CH2 CH2 H

10-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

10-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

10-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

10-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

10-71 4-methoxy-phenyl CH2 CH2 CH2 H

10-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

10-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

10-74 4-fluor-phenyl CH2 CH2 CH2 H

10-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

10-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

10-77 2-chlor-phenyl CH2 CH2 CH2 H

10-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl WO-A 2007/060164

Tabelle 11

Verbindungen der Formel I-l 1

1-11

Physikalische Daten: 'H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

11-1 3 -methyl-2-thienyl CH2 CH2 - H

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

11-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 1 1 -3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,324 (1 ,4); 8,3105 (2,59); 8,2971 (1 ,42); 7,4819 (9,92); 7,4674 (10,93); 7,3651 (1 ); 7,3588 (9,04); 7,3541 (3,3); 7,3429 (4,14); 7,3378 (16); 7,3319 (2,25); 7,2844 (2,06); 7,2787 (13,94); 7,2739 (3,99); 7,2623 (3,01 ); 7,2576 (8,33); 7, 1841 (1 1 ,46); 7, 1696 (10,53); 3,454 (2,82); 3,4366 (5,79); 3,4219 (5,7); 3,4038 (3, 12); 3,3268 (91 ,94); 2,8304 (5,17); 2,8122 (9,02); 2,7944 (4,63); 2,6754 (0,35); 2,6708 (0,48); 2,6663 (0,37); 2,541 1 (16,41 ); 2,5241 (1 ,28); 2,5107 (25,83); 2,5062 (51 ,84); 2,5017 (69,01 ); 2,4971 (50,97); 2,4926 (24,86); 2,3331 (0,32); 2,3284 (0,44); 2,3238

11-3 4-chlor-phenyl CH2 CH2 H (0,32); 2,0747 (0,45); -0,0002 (7,87)

Verbindung Nr. 1 1 -4, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3622 (1 ,12); 8,3484 (2, 12); 8,3344 (1 ,12); 7,5825 (6,36); 7,5799 (3,86); 7,4827 (7,29); 7,4682 (7,98); 7,3726 (16); 7,3695 (15,8); 7, 1861 (8,69); 7, 1716 (8,04); 3,4845 (1 ,92); 3,4673 (4,73); 3,4524 (4,82); 3,4352 (2,13); 3,33 (28,07); 2,9532 (4,09); 2,9358 (7,84); 2,9183 (3,59); 2,5426 (10,86); 2,5256 (0,54); 2,5123 (9,2); 2,5078 (18,09); 2,5032 (23,82); 2,4987 (17,46); 2,4942

11-4 2,4-dichlor-phenyl CH2 CH2 H (8,49); -0,0002 (2,82)

11-5 4-chlor-phenyl CH(0CH3) CH(CH3) - H

11-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

Verbindung Nr. 1 1 -7, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2745 (1 ,71 ); 8,2608 (3,17); 8,247 (1 ,75); 7,4645 (7,07); 7,45 (7,68); 7,3619 (7,04); 7,3409 (13,53); 7,2937 (13,14); 7,2726 (7,41 ); 7,1296 (8); 7,1 151 (7,43);

11-7 4-chlor-phenyl CH(CH3) CH2 H 3,4038 (0,52); 3,3856 (0,82); 3,3709

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

(2,68); 3,3532 (5,26); 3,3369 (5,77); 3,3265 (12,28); 3,3033 (0,9); 3,2886 (0,6); 3,0809 (0,35); 3,0631 (1,51); 3,0454 (2,93); 3,0275 (2,85); 3,0097 (1,37); 2,5023 (34,43); 2,4985 (28,1); 1,9893 (0,45); 1,3969 (1,19); 1,2488 (0,38); 1,2259(16); 1,2084 (15,92); 1,1753 (0,37); -0,0002 (17,97)

Verbindung Nr.11-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3291 (1,78); 8,3149 (3,46); 8,3011 (1,85); 7,558 (6,34); 7,5528 (6,84); 7,4712 (4,61); 7,4635 (7,51); 7,4495 (15,86); 7,4173 (5,42); 7,4122 (5,15); 7,3962 (2,53); 7,3911 (2,49); 7,1338 (7,92); 7,1192 (7,36); 4,0385 (0,77); 4,0208 (0,78); 3,5511 (1,19); 3,5336 (2,64); 3,5162 (3,05); 3,4991 (1,9); 3,4859 (1,53); 3,4717 (1 ,35); 3,4541 (2,88); 3,4385 (3,59); 3,4224 (3,86); 3,4074 (2,92); 3,3895 (2,56); 3,3749 (1,09); 3,3567 (0,7); 3,3263 (22,58); 2,5028 (45,05); 1,9897 (3,21); 1,3972 (12,85); 1,2492 (0,33); 1,2167 (15,99); 1,1997 (16); 1,1755 (1,91); 1,1576

11-8 2,4-dichlor-phenyl CH(CH3) CH2 H (0,94); -0,0002 (20,68)

Verbindung Nr.11-9, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1383 (2,47); 8,1177 (2,5); 7,4695 (8,58); 7,4551 (9,27); 7,3752 (0,42); 7,3469 (0,87); 7,3408 (7,51); 7,3361 (2,74); 7,3247 (3,61); 7,3198 (13,82); 7,3141 (2,01); 7,2672 (12,32); 7,2461 (6,96); 7,1445 (9,23); 7,13 (8,54); 4,1754 (0,66); 4,1557 (1,41); 4,1392 (2,05); 4,1226 (1,49); 4,103 (0,67); 3,3281 (112,12); 2,9958 (0,65); 2,8303 (1,33); 2,8106 (1,27); 2,7967 (3,33); 2,7769 (3,33); 2,7601 (3,34); 2,7445 (3,38); 2,7265 (1,35); 2,711 (1,31); 2,671 (0,39); 2,5413 (31,42); 2,5244 (1,22); 2,5108 (22,6); 2,5065 (44,94); 2,5019 (59,63);

11-9 4-chlor-phenyl CH2 CH(CH3) H 2,4974 (44,12); 2,493 (21,73); 2,3286

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

(19,1 1 ); 2,3289 (0,36); -0,0002 (7,54)

Verbindung Nr. 1 1 -16, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3321 (1 ,58); 8,3187 (2,87); 8,3052 (1 ,58); 7,4839 (14,27); 7,4694 (15,38); 7,359 (0,35); 7,3448 (3, 19); 7,3378 (0,88); 7,3247 (15,14); 7,3198 (5,47); 7,3066 (7,88); 7,2798 (4,31 ); 7,2767 (6,14); 7,2745 (4,01 ); 7,2716 (4,33); 7,26 (2,29); 7,2564 (2,53); 7,2549 (2,51 ); 7,2516 (1 ,75); 7,225 (3,71 ); 7,2216 (5,76); 7,2064 (2,76); 7,2028 (4,04); 7, 1998 (2,42); 7,1841 (0,59); 7, 174 (16); 7, 1651 (0,58); 7,1595 (14,79); 3,473 (3,4); 3,4555 (7,36); 3,441 1 (7,38); 3,4232 (3,88); 3,3282 (144,3); 3,3127 (0,6); 2,8515 (6,04); 2,8337 (1 1 ,28); 2,816 (5,48); 2,6755 (0,43); 2,6709 (0,63); 2,6664 (0,43); 2,554 (0,38); 2,5412 (42,89); 2,5243 (1 ,78); 2,5196 (2,86); 2,51 1 (31 ,99); 2,5064 (64,24); 2,5018 (85,45); 2,4972 (61 ,99); 2,4926 (29,23); 2,3332 (0,42); 2,3286 (0,56); 2,3241 (0,4); 2,0746 (0,37); 0,008 (0,37);

11-15 3,5- dichlor-pheny 1 CH2 CH2 H -0,0002 (1 1 ,24); -0,0085 (0,32)

Verbindung Nr. 1 1 -17, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3767 (1 ,9); 8,3634 (3,37); 8,3495 (1 ,86); 7,481 1 (1 1 ,89); 7,4666 (13,01 ); 7,339 (2,1 ); 7,3352 (2,47); 7,3205 (4,24); 7,316 (5,16); 7,2973 (3,78); 7,2847 (1 ,38); 7,2799 (2,86); 7,2653 (2,86); 7,2597 (3,62); 7,2552 (1 ,99); 7,246 (2,03); 7,2415 (1 ,67); 7, 1895 (13,78); 7, 175 (16); 7,1526 (8,37); 7,1361 (6,92); 7, 1334 (6,68); 7,1 178 (2,86); 7,1 15 (2,54); 3,4647 (3,72); 3,4477 (7,58); 3,4323 (7,23); 3,4141 (4,05); 3,3283 (141 ,3); 2,878 (5,94); 2,8599 (10,29); 2,8418 (5,24); 2,6755 (0,46); 2,6709 (0,58); 2,6664 (0,42); 2,5413 (37,08); 2,5107 (34,65); 2,5064 (67,03); 2,5019

11-16 3-chlor-phenyl CH2 CH2 H (88,23); 2,4974 (65,69); 2,4931 (32,79);

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

(3,53); 7,5622 (16); 7,5494 (9,65); 7,5371 (3,76); 7,5256 (1,78); 7,5133 (1,26); 7,4932 (0,47); 7,4801 (14,24); 7,4656 (15,49); 7,1809 (0,59); 7,1663 (0,71); 7,156 (15,92); 7,1415 (14,7); 3,5098 (4,08); 3,4924 (10,09); 3,4779 (10,2); 3,4606 (4,58); 3,3562 (0,52); 3,3286 (201,14); 3,3061 (0,64); 2,949 (7,48); 2,9315 (14,75); 2,9141 (6,7); 2,6761 (0,54); 2,6714 (0,73); 2,6668 (0,53); 2,5416 (50,7); 2,5246 (2,16); 2,5113 (41,94); 2,5069 (82,27); 2,5023 (108,16); 2,4978 (78,98); 2,4933 (38,15); 2,3335 (0,48); 2,329 (0,68); 2,3245 (0,48); 2,0749 (0,47); 0,0079 (0,44); - 0,0002 (11 ,06); -0,0084 (0,35)

Verbindung Nr.11-21, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3587 (1,15); 8,345 (2,15); 8,331 (1,14); 7,6683 (5,85); 7,6483 (7,14); 7,4864 (7,11); 7,4832(14,15); 7,4686(16); 7,1809 (11,51); 7,1664 (10,68); 3,5062 (2,2); 3,4889 (4,78); 3,4743 (4,78); 3,4564 (2,44); 3,3283 (114,84); 2,9386 (3,41); 2,9209 (6,32); 2,9031 (3); 2,6714 (0,4); 2,5416 (1,14); 2,5248 (1,33); 2,5201 (2,07); 2,5115(22,77); 2,5069 (45,71); 2,5023 (60,81); 2,4977 (44,06); 2,4931 (20,85); 2,3291 (0,4); -0,0002

11-20 3 -(trifluormethyl)-phenyl CH2 CH2 H (8,15)

Verbindung Nr.11-22, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3927 (0,54); 8,3785 (1); 8,3649 (0,54); 7,4914 (4,51); 7,4769 (4,99); 7,224 (5,11); 7,2095 (4,71 ); 7, 1729 (0,82); 7,1649 (1,47); 7,1617 (1,1); 7,1537 (2,34); 7,1505 (2,52); 7,144 (2,2); 7,1362 (1,07); 7,1301 (0,82); 7,125 (3); 7,1214 (3,18); 7,1183 (1,49); 7,1122 (2,9); 7,1059 (1,29); 7,1 (1,47); 3,4032 (1,17); 3,3881 (1,96); 3,3846 (1,6); 3,3798 (1,13); 3,3727 (1 ,28); 3,3698 (1 ,58);

11-21 4-(trifluormethyl)-phenyl CH2 CH2 H 3,365 (2,11); 3,3504 (1,4); 3,3279

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ oder CAS- bzw. Patent-Nr.

(50,23); 2,8321 (2,25); 2,8168 (1,73); 2,8124 (2,5); 2,7938 (2,01); 2,5408 (12,42); 2,524 (0,59); 2,5191 (0,91); 2,5106 (11,37); 2,5061 (22,79); 2,5015 (30,32); 2,4968 (22,05); 2,4923 (10,49); 2,3193(16); -0,0002 (3,87)

Verbindung Nr.11-23, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4846 (0,48); 8,4704 (0,88); 8,4564 (0,48); 7,5054 (1,96); 7,4908 (2,16); 7,2682 (2,2); 7,2537 (2); 6,8072 (4,44); 3,3271 (31,98); 3,2443 (0,62); 3,2295 (1,12); 3,2158 (1 ,08); 3,2087 (0,96); 3,2031 (1,11); 3,1888 (0,7); 2,8004 (1 ,25); 2,7867 (1 ,05); 2,7792 (1 ,32); 2,7596 (1,02); 2,5409 (4,06); 2,5056 (16,7); 2,5014 (20,02); 2,4971 (15,02);

11-22 2-methyl-phenyl CH2 CH2 H 2,297 (16); 2,1819 (7,29); -0,0002 (1,53)

Verbindung Nr.11-25, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3377 (1,59); 8,3247 (2,81); 8,3109 (1,58); 7,4827 (13,01); 7,4682 (14,31); 7,3191 (3,86); 7,3153 (1,65); 7,3008 (10,29); 7,2874 (3,19); 7,2828 (10,7); 7,256 (9,52); 7,252 (13,53); 7,2467 (2,78); 7,2352 (6,55); 7,2256 (3,21); 7,2219 (3,53); 7,2181 (1,9); 7,2092 (2,15); 7,204 (5,95); 7,1998 (16); 7,1853 (15,1); 3,4592 (3,82); 3,4413 (5,92); 3,4268 (5,78); 3,4227 (6,18); 3,4078 (4,19); 3,3276 (137,01); 2,8379 (6,65); 2,8187 (9,34); 2,8007 (5,92); 2,6752 (0,47); 2,6705 (0,61); 2,666 (0,43); 2,5408 (30,04); 2,5239 (1,92); 2,519 (2,92); 2,5105 (34,19); 2,506 (68,14); 2,5014 (90,31); 2,4968 (65,75); 2,4923 (31,3); 2,3327 (0,42); 2,3282 (0,58); 2,3236 (0,41); 2,0741 (0,68); 0,008

11-23 2,4,6-trimethyl-phenyl CH2 CH2 H (0,38); -0,0002 (11,51 ); -0,0085 (0,32)

Verbindung Nr.11-7, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2745 (1,71); 8,2608 (3,17); 8,247

11-24 3 ,4-bismethoxy-phenyl CH2 CH2 H (1 ,75); 7,4645 (7,07); 7,45 (7,68); 7,3619

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

(7,04); 7,3409 (13,53); 7,2937 (13,14); 7,2726 (7,41); 7,1296(8); 7,1151 (7,43); 3,4038 (0,52); 3,3856 (0,82); 3,3709 (2,68); 3,3532 (5,26); 3,3369 (5,77); 3,3265 (12,28); 3,3033 (0,9); 3,2886 (0,6); 3,0809 (0,35); 3,0631 (1,51); 3,0454 (2,93); 3,0275 (2,85); 3,0097 (1,37); 2,5023 (34,43); 2,4985 (28,1); 1,9893 (0,45); 1,3969 (1,19); 1,2488 (0,38); 1,2259(16); 1,2084 (15,92); 1,1753 (0,37); -0,0002 (17,97)

Verbindung Nr.11-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3291 (1,78); 8,3149 (3,46); 8,3011 (1,85); 7,558 (6,34); 7,5528 (6,84); 7,4712 (4,61); 7,4635 (7,51); 7,4495

(15,86); 7,4173 (5,42); 7,4122 (5,15); 7,3962 (2,53); 7,3911 (2,49); 7,1338 (7,92); 7,1192 (7,36); 4,0385 (0,77); 4,0208 (0,78); 3,5511 (1,19); 3,5336 (2,64); 3,5162 (3,05); 3,4991 (1,9); 3,4859 (1,53); 3,4717 (1 ,35); 3,4541 (2,88); 3,4385 (3,59); 3,4224 (3,86); 3,4074 (2,92); 3,3895 (2,56); 3,3749 (1,09); 3,3567 (0,7); 3,3263 (22,58); 2,5028 (45,05); 1,9897 (3,21); 1,3972 (12,85); 1,2492 (0,33); 1,2167 (15,99); 1,1997 (16); 1,1755 (1,91); 1,1576

11-25 phenyl CH2 CH2 H (0,94); -0,0002 (20,68)

11-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

11-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

11-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

11-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

11-30 4-chlor-phenyl 0 CH2 CH2 H

11-31 2,4-dichlor-phenyl 0 CH2 CH2 H

11-32 4-chlor-phenyl CH2 CH2 CH2 H

11-33 4-chlor-phenyl NCH3 CH2 CH2 H

11-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

11-35 4-chlor-phenyl CH(OCH3) CH2 - H

11-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 1 1-37, Solvent: [DMSO], Spektrometer: 399.95MHz 8,4093 (1 ,8); 8,3956 (3,2); 8,3822 (1 ,77); 7,4959 (13,95); 7,4813 (15,41 ); 7,3512 (6,88); 7,3481 (7,15); 7,3384 (7,63); 7,3354 (7,39); 7,2335 (16); 7,219 (14,45); 6,9708 (5,81 ); 6,9623 (8,32); 6,9581 (5,41 ); 6,9496 (8,12); 6,9238 (6,96); 6,9215 (7,3); 6,9155 (4,9); 6,913 (4,71 ); 3,4761 (4,02); 3,4583 (8,51 ); 3,4439 (8,66); 3,4404 (6,22); 3,4258 (4,68); 3,3277 (170,52); 3,3062 (0,39); 3,0561 (7,24); 3,0383 (12,69); 3,0202 (6,06); 2,675 (0,47); 2,6705 (0,64); 2,6658 (0,47); 2,5408 (45,14); 2,5238 (1 ,96); 2,5189 (3,1 1 ); 2,5104 (36,74); 2,5059 (73,63); 2,5013 (97,89); 2,4968 (71 ,63); 2,4923 (34,49); 2,3327 (0,44); 2,3281 (0,61 ); 2,3235 (0,45); 2,0742 (0,49); 0,008 (0,35); -0,0002 (10,89)

11-37 2-thienyl CH2 CH2 H

11-38 3-thienyl CH2 CH2 - H

11-39 2-furyl CH2 CH2 - H

11-40 3-furyl CH2 CH2 - H

11-41 phenyl CH2 CH2 CH(CH3) H

11-42 phenyl CH2 CH2 CH2 H

11-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

11-44 4-t-butyl-phenyl CH2 CH2 CH2 H

11-45 4-methyl-phenyl CH2 CH2 CH2 H

11-46 phenyl CH2 CH2 CH(CH2CH3) H

11-47 2-methoxy-phenyl CH2 CH2 CH2 H

11-48 2-methyl-phenyl CH2 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

11-49 3 -methyl-phenyl CH2 CH2 CH2 H

11-50 3-chlor-phenyl CH2 CH2 CH2 H

11-51 2,6-difluor-phenyl CH2 CH2 CH2 H

11-52 4-chlor-phenyl CH2 CH2 CH2 H

11-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

11-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

11-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

11-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

11-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

11-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

11-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

11-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

11-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

11-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

11-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

11-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

11-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

11-66 4-phenoxy-phenyl CH2 CH2 CH2 H

11-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

11-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

11-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

11-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

11-71 4-methoxy-phenyl CH2 CH2 CH2 H

11-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

11-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

11-74 4-fluor-phenyl CH2 CH2 CH2 H

11-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ L ² L ³ Y oder CAS- bzw. Patent-Nr.

11-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

11-77 2-chlor-phenyl CH2 CH2 CH2 H

11-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Verbindung Nr.11-79, Solvent: [DMSO], Spektrometer: 399.95MHz

8,346 (0,51); 8,3319 (0,98); 8,3169 (0,52); 7,4778 (2,93); 7,4632 (3,31); 7,4523 (2,92); 7,4479 (1,11); 7,436 (1,26); 7,4312 (4,69); 7,4257 (0,71); 7,36 (4,42); 7,3389 (2,8); 7,1917 (3,31); 7,1772 (3,03); 4,4049 (0,83); 4,3894 (1 ,47); 4,373 (0,88); 3,4211 (0,97); 3,4123 (1,06); 3,4068 (1,24); 3,4041 (1,33); 3,3976 (1,8); 3,3899 (1,01); 3,3829 (0,95); 3,3214 (14,07); 3,1713 (16); 2,5238 (0,82); 2,5104 (12,71); 2,506 (25,27); 2,5015 (33,73); 2,497

11-79 4-chlor-phenyl CH(OCH3) CH2 H (25,32); 2,4927 (12,7); -0,0002 (1 ,91 )

Verbindung Nr.11-80, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3571 (0,64); 8,3429 (1,2); 8,3295 (0,65); 8,3151 (0,39); 7,4802 (3,24); 7,4657 (3,5); 7,1859 (0,54); 7,1768

(4.22) ; 7,1716 (1,62); 7,156 (6,44); 7,1418 (3,48); 6,764 (0,58); 6,7555 (4,42); 6,7328 (3,91); 6,7239 (0,45); 3,4846 (1,24); 3,4676 (2,95); 3,4512

(2.23) ; 3,378 (1,52); 3,3628 (3,09); 3,3268 (337,58); 3,2827 (0,56); 2,9343 (0,72); 2,9132 (16); 2,6751 (0,92); 2,6707 (1,23); 2,6666 (0,91); 2,5409 (7,25); 2,5061 (147,5); 2,5017 (188,35); 2,4973 (139,99); 2,3328 (0,95); 2,3285 (1,25); 2,3241 (0,93); 0,0077 (1,16); -

11-80 4-chlor-phenyl N(CH3) CH2 CH2 H 0,0003 (24,24); -0,0086 (1,12)

Tabelle 12

Verbindungen der Formel 1-12

1-12

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppml oder CAS- bzw. Patent-Nr.

12-1 3 -methyl-2-thienyl CH2 CH2 - H

Verbindung Nr. 12-2, Solvent: [DMSO], Spektrometer: 399.95MHz 8,3521 (1 ,86); 8,3384 (3,5); 8,3246 (1 ,85); 7,6354 (13,63); 7,621 1 (14,47); 7,5685 (9); 7,5632 (9,4); 7,433 (6,12); 7,4123 (13,13); 7,3828 (8,55); 7,3775 (7,98); 7,3621 (3,81 ); 7,3568 (3,76); 7,207 (16); 7, 1988 (0,63); 7,1927 (15,22); 3,5145 (0,52); 3,3343 (52,66); 3,2728 (3,31 ); 3,2557 (7,93); 3,2409 (7,97); 3,2238 (3,44); 2,7614 (5,95); 2,7425 (7,24); 2,7226 (6,35); 2,544 (28,04); 2,5271 (0,65); 2,5222 (0,99); 2,5136 (12,37); 2,5091 (25,04); 2,5045 (33,42); 2,4999 (24,37); 2,4954 (1 1 ,58); 1 ,819 (1 ,71 ); 1 ,801 1 (4,5); 1 ,7821 (5,68); 1 ,7634 (4,33); 1 ,7456 (1 ,51 ); -0,0002 (4,14)

12-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz 8.3531 (1.66); 8.3395 (3.09); 8.3258 (1.65); 7.6271 (10.73); 7.6128 (1 1.25); 7.3689 (1.14); 7.3627 (9.27); 7.3579 (3.66); 7.3466 (4.48); 7.3416 (16.00); 7.3357 (2.73); 7.2857 (14.23); 7.2692 (3.39): 7.2645 (8.46); 7.1601 (1 1.40); 7.1458 (10.88); 3.4522 (2.83); 3.4349 (5.97): 3.4200 (5.81); 3.4020 (3.12); 3.3459 (18.77); 2.8345 (5.41); 2.8164 (9.21 ): 2.7985 (4.75); 2.5436 (4.58); 2.5266 (0.41); 2.5218 (0.61); 2.5131 (7.31 ); 2.5087 ( 14.83); 2.5042 (19.72);

12-3 4-chlor-phenyl CH2 CH2 H 2.4997 (14.85); 2.4953 (7.53); -0.0002 (6.24)

[DMSO], Spektrometer: 399.95MHz

12-4 2,4-dichlor-phenyl CH2 CH2 - H 8.3827 (1.20); 8.3689 (2.31 ); 8.3551 (1.19); 7.6272 (7.73); 7.6130 (8.21 );

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 |ppm] oder CAS- bzw. Patent-Nr.

7.5924 (3.75); 7.5898 (6.55); 7.5869 (4.05); 7.3796 ( 16.00); 7.3766 (15.68); 7.1564 (8.02); 7.1421 (7.63); 3.4760 (1.81 ); 3.4588 (4.60); 3.4437 (4.66); 3.4267 (2.04); 3.3355 (126.32); 3.3131 (0.35); 2.9517 (3.91); 2.9342 (7.57); 2.9168 (3.44); 2.6759 (0.61); 2.6713 (0.84); 2.6668 (0.62); 2.5418 (12.45); 2.5247 (2.68); 2.51 12 (45.90); 2.5068 (93.39); 2.5022 (124.88); 2.4977 (93.92); 2.4933 (47.45); 2.3336 (0.59); 2.3290 (0.83); 2.3246 (0.62); 0.0080 (1.23); -0.0002 (39.06); -0.0085 (1.53)

[DMSO], Spektrometer: 399.95MHz 8.1677 (1.14); 8.1461 (1.16); 8.0316 (0.91 ): 8.01 15 (0.92); 7.6200 (2.69); 7.6058 (2.90); 7.5969 (3.53); 7.5827 (3.63): 7.4445 (2.70); 7.4403 (i .05); 7.4270 (4.17); 7.4235 (5.00); 7.4107 (1.49); 7.4059 (5.32); 7.3445 (4.85); 7.3238 (6.23); 7.3031 (2.59); 7.1741 (2.82); 7.1598 (2.70); 7.0188 (3.55); 7.0046 (3.45); 4.3154 (1.44); 4.3003 (1.83); 4.2305 (1.96); 4.2139 (2.72); 4.1965 (0.69); 4.1777 (0.64); 4.161 1 (0.39); 4.0941 (0.57); 4.0773 (0.89); 4.0728 (0.70); 4.0604 (0.63); 4.0559 (0.90); 4.0391 (0.52); 3.3426 (14.99); 3.1828 (16.00); 3.1636 (12.86); 2.5435 (4.51 ); 2.5130 (5.58); 2.5087 (1 1.35); 2.5041 (15.15); 2.4996 (1 1.48); 2.4953 (5.90); 1.1524 (6.20);

12-5 4-chlor-phenyl CH(0CH3) CH(CH3) H 1.1355 (6.18); 0.9758 (4.73); 0.9587 (4.70); -0.0002 (4.29)

12-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz 8.3039 (1.48); 8.2899 (2.87); 8.2756 (1.51); 7.6091 (9.53); 7.5948 (10.00); 7.3722 (0.88); 7.3663 (7.56); 7.3614 (2.91 ); 7.3501 (3.85); 7.3450 (14.62); 7.3393 (2.53); 7.3055 (2.22); 7.3002 (13.56): 7.2953 (4.05); 7.2835 (2.78); 7.2789 (7.33); 7.1006 (9.98); 7.0863 (9.59): 3.4004 (0.53); 3.3850 (0.69); 3.3818 (0.76); 3.3673 (2.66); 3.3438 (21.19): ί.ίίί9 (5.14); 3.3169 (2.93); 3.3022 (0.66); 3.2985 (0.77); 3.2842 (0.59); 3.0643 (1.39); 3.0465 (2.77); 3.0287 (2.68); 3.0108 (1.26); 2.5434 (3.93); 2.5265 (0.36); 2.5215 (0.54); 2.5130 (7.13); 2.5086 (14.55); 2.5040 (19.46); 2.4995 ( 14.72); 2.4952

12-7 4-chlor-phenyl CH(CH3) CH2 H (7.56); 1.2340 (16.00); 1.2165 (15.81); -0.0002 (5.65)

[DMSO], Spektrometer: 399.95MHz 8.3540 (1.52); 8.3397 (2.97); 8.3255 (1.54); 8.3223 (1.47); 7.6089 (9.43); 7.5946 (9.98); 7.5638 (7.41); 7.5585 (7.90); 7.4769 (4.67); 7.4557 (9.53); 7.4215 (5.64); 7.4161 (5.24); 7.4004 (2.71 ); 7.3951 (2.63); 7.1065 (10.03); 7.0922 (9.64); 3.5477 (1.10); 3.5303 (2.51 ); 3.5130 (2.89); 3.4958 (1.76); 3.4830 (1.42); 3.4687 (1.31); 3.4511 (2.77); 3.4356 (3.09); 3.4170 (2.67); 3.4016 (2.58); 3.3835 (2.49); 3.3691 (1.09); 3.3660 (1.00); 3.3405 (28.82); 2.5434 (5.88); 2.5264 (0.75); 2.5129 (12.07); 2.5086 (24.01); 2.5040 (31.64); 2.4995 (23.61); 2.4952 (1 1.92); 1.4586 (0.34); 1.2241 (16.00);

12-8 2,4-dichlor-phenyl CH(CH3) CH2 H 1.2071 (15.79); -0.0002 (8.22); -0.0085 (0.34)

[DMSO], Spektrometer: 399.95MHz 8.1645 (2.67); 8.1440 (2.71); 7.6151 (9.36): 7.6009 (9.83); 7.4696 (0.47); 7.3522 (0.85); 7.3462 (7.80); 7.3415 (2.95); 7.3301 (3.80); 7.3251 (14.28); 7.3194 (2.28); 7.2725 (12.62); 7.2514 (7.20); 7.1 143 (9.87); 7.1001 (9.41 );

12-9 4-chlor-phenyl CH2 CH(CH3) H 4.1697 (0.66); 4.1503 (1.45); 4.1336 (2.09); 4.1 169 (1.53); 4.0976 (0.70);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

3.3395 (50.45); 2.9978 (0.55); 2.8343 (1.45); 2.8147 ( 1.41); 2.8007 (3.21); 2.781 1 (3.19); 2.7553 (3.23); 2.7396 (3.31); 2.7217 (1.50); 2.7060 (1.35); 2.5423 (26.31 ); 2.5254 (0.90); 2.5205 (1.33); 2.51 18 (17.41); 2.5074 (35.27); 2.5029 (46.85); 2.4983 (35.21); 2.4939 (17.89); 1.1401 (16.00); 1.1236 (15.93); 0.0080 (0.38); -0.0002 (12.17); -0.0085 (0.50)

[DMSO], Spektrometer: 399.95MHz 8.2004 (2.78); 8.1790 (2.87); 7.6185 (9.67); 7.6042 (10.31 ); 7.5727 (6.1 1); 7.5682 (6.35); 7.5573 (0.58); 7.5523 (0.33); 7.3941 (1.81 ); 7.3735 (10.64); 7.3678 (8.82); 7.3630 (8.00); 7.3471 (1.37); 7.3423 (1.67); 7.1 163 (9.94); 7.1021 (9.58); 4.3105 (0.60); 4.2898 (1.42); 4.2735 (1.87); 4.2576 (1.31); 4.2367 (0.64); 3.3379 (793.49); 2.9388 (0.95); 2.9239 (1.21); 2.9045 (4.14); 2.8893 (7.23); 2.8679 (3.64); 2.8546 (1.03); 2.8338 (1.09); 2.6759 (2.15); 2.6713 (3.02); 2.6668 (2.27); 2.5417 (6.08); 2.5248 (8.92); 2.5200 (13.44); 2.51 12 (158.61); 2.5068 (325.54); 2.5023 (436.98); 2.4977 (330.10); 2.4933 (167.93); 2.3379 (0.97); 2.3336 (2.09); 2.3290 (2.90); 2.3245 (2.19); 1.1868

12-10 2,4-dichlor-phenyl CH2 CH(CH3) H (16.00); 1.1702 (15.87); 0.0080 (2.04); -0.0002 (61.12); -0.0085 (2.26)

[DMSO], Spektrometer: 399.95MHz 8.11 10 (0.51 ); 8.0956 (1.00); 8.0801 (0.51); 7.5962 (3.37); 7.5820 (3.53); 7.4555 (0.35); 7.4487 (2.98); 7.4436 (1.15); 7.4321 (1.42); 7.4269 (4.94); 7.4203 (0.77); 7.371 1 (0.69); 7.3645 (4.97); 7.3593 (1.46); 7.3477 (1.09); 7.3427 (2.99); 7.3360 (0.37); 7.0825 (3.55); 7.0683 (3.41 ); 3.4141 (3.37); 3.3982 (3.35); 3.3440 (6.40); 2.5433 (2.1 1 ); 2.5128 (2.24); 2.5084 (4.44);

12-1 1 4-chlor-phenyl C(CH3)2 CH2 H 2.5039 (5.84); 2.4994 (4.38); 2.4951 (2.20); 1.3075 (16.00); -0.0002 (1.51)

[DMSO], Spektrometer: 399.95MHz 8.1079 (0.60); 8.0923 (1.19); 8.0767 (0.60); 7.5849 (3.47); 7.5707 (3.62); 7.5197 (2.71); 7.5139 (2.93); 7.4941 (2.06); 7.4724 (2.84); 7.3706 (1.81); 7.3648 (1.73); 7.3490 (1.33); 7.3432 (1.29); 7.0520 (3.91); 7.0378 (3.78); 3.7589 (3.57); 3.7430 (3.55); 3.3450 (6.00); 2.5443 (2.75); 2.5138 (1.93); 2.5095 (3.90); 2.5050 (5.19); 2.5005 (3.94); 2.4963 (2.03); 1.4603 (16.00); -

12-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 0.0002 (1.31)

[DMSO], Spektrometer: 399.95MHz 8.4127 (2.48); 8.3990 (4.61); 8.3852 (2.47); 7.6280 ( 15.19); 7.6137 (16.00); 7.4427 (5.76); 7.4388 (5.01 ); 7.4243 (7.64); 7.4197 (7.42); 7.3771 (4.40); 7.3719 (5.36); 7.3585 (6.21 ); 7.3539 (7.66); 7.31 15 (2.49); 7.3074 (3.25); 7.2932 (7.49); 7.2891 (7.31 ); 7.2759 (1 1.33); 7.2705 ( 10.51); 7.2574 (6.18); 7.2523 (5.81); 7.2388 (2.14); 7.2340 (1.79); 7.1805 ( 15.75); 7.1662 (14.99); 3.4881 (4.06); 3.471 1 (8.61); 3.4557 (8.12); 3.4531 (8.32); 3.4376 (4.61); 3.3496 (21.16); 2.9774 (8.27); 2.9589 (13.18); 2.9413 (7.23); 2.5443 (1 1.48); 2.5273 (0.45); 2.5137 (7.95); 2.5094 (16.09); 2.5049 (21.36);

12-13 2-chlor-phenyl CH2 CH2 H 2.5004 (16.25); 2.4962 (8.34); -0.0002 (5.49)

[DMSO], Spektrometer: 399.95MHz 8.3492 (2.08); 8.3354 (3.92); 8.3217 (2.09); 7.6322 (1 1.80); 7.6179 (12.44); 7.5574 (8.96); 7.5363 (16.00); 7.5302 (9.94); 7.2643 (5.49); 7.2593 (5.34);

12-14 3,4-dichlor-phenyl CH2 CH2 H 7.2438 (4.80); 7.2387 (4.73); 7.1441 (13.25); 7.1298 (12.72); 3.4797 (3.29);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.2160 (4.84); 7.2136 (5.48); 7.2102 (5.22); 7.2039 (1 1.34); 7.1997 (7.87); 7.1901 (8.73); 3.4516 (1 1.1 1); 3.4373 (10.24); 3.4202 (4.23); 3.3591 (7.73); 3.3569 (7.79); 3.3501 (14.35); 3.1542 (12.93); 3.1373 (6.04); 2.5588 (3.42); 2.5564 (3.78); 2.5531 (3.35); 2.5493 (4.50); 2.5466 (5.87); 2.51 16 (26.16); 0.0128 (1.90); 0.0103 (2.09); 0.0069 (1.81); 0.0031 (2.34); -0.0002 (2.93)

[DMSO], Spektrometer: 399.95MHz 8.3732 (2.25); 8.3596 (4.09); 8.3459 (2.18); 7.6733 (0.40); 7.6533 (0.57); 7.6414 (0.52); 7.6293 (14.31 ); 7.6150 ( 16.00); 7.6061 (8.70); 7.5919 (2.71); 7.5885 (2.82); 7.5824 (3.33); 7.5670 (13.64); 7.5542 (9.1 1 ); 7.5429 (2.88); 7.5367 (2.18); 7.5178 (1.30); 7.4960 (0.47); 7.4759 (0.38); 7.1613 (0.56); 7.1470 (0.66); 7.1370 (14.42); 7.1227 (13.77); 3.51 14 (3.59); 3.4940 (8.81); 3.4794 (8.80); 3.4620 (4.13); 3.3522 (15.80); 2.9556 (6.78); 2.9380 (12.80); 2.9204 (6.09); 2.5461 (16.30); 2.5292 (0.41); 2.5244 (0.61); 2.5157 (7.12);

3 -(trifluormethyl)- 2.51 13 (14.54); 2.5068 (19.44); 2.5022 (14.72); 2.4979 (7.52); -0.0002

12-20 phenyl CH2 CH2 H (6.35)

[DMSO], Spektrometer: 399.95MHz 8.3905 (2.28); 8.3768 (4.30); 8.3631 (2.28); 7.6732 ( 10.42); 7.6531 (12.81); 7.6305 (14.27); 7.6162 (15.04); 7.4955 (1 1.97); 7.4755 (9.94); 7.1598 (16.00); 7.1455 (15.29); 3.5068 (3.65); 3.4894 (8.31 ); 3.4746 (8.25); 3.4569 (4.1 1 ); 3.3486 (17.26); 2.9447 (6.12); 2.9269 (1 1.15); 2.9091 (5.42); 2.5456

4-(trifluormethyl)- (0.65); 2.5287 (0.50); 2.5239 (0.76); 2.5152 (8.81 ); 2.5108 ( 17.77); 2.5062

12-21 phenyl CH2 CH2 H (23.54); 2.5017 (17.68); 2.4973 (8.95); -0.0002 (8.01 )

[DMSO]. Spektrometer: 399.95MHz 8.4223 (0.79); 8.4084 (1.48); 8.3945 (0.80); 7.6351 (4.68); 7.6209 (4.99); 7.2019 (5.30); 7.1876 (5.10); 7.1795 (1.17); 7.1714 (1.73); 7.1677 (1.68); 7.1561 (3.52); 7.1462 (2.76); 7.1407 (1.34); 7.1286 (3.25); 7.1236 (3.88); 7.1150 (3.97); 7.1072 (1.73); 7.1056 (1.79); 7.1024 (1.59); 7.0897 (0.34); 3.4021 (1.35); 3.3869 (2.36); 3.3788 (1.50); 3.3687 (1.99); 3.3639 (2.51); 3.3479 (7.52); 2.8379 (2.66); 2.8180 (3.12); 2.7994 (2.37); 2.5420 (3.48); 2.51 14 (2.36); 2.5072 (4.75); 2.5027 (6.30); 2.4982 (4.76); 2.4941 (2.44);

12-22 2-methyl-phenyl CH2 CH2 H 2.3229 (16.00); -0.0002 (1.93)

[DMSO], Spektrometer: 399.95MHz 8.51 14 (0.56); 8.4970 (1.1 1 ); 8.4825 (0.58); 7.6494 (2.65); 7.6352 (2.84); 7.2473 (2.77); 7.2330 (2.63); 6.8076 (5.31 ); 3.3461 (4.45); 3.2423 (0.67); 3.2276 (1.18); 3.2139 (1.17); 3.2070 (1.00); 3.2006 (1.27); 3.1866 (0.81); 2.8069 (1.42); 2.7936 (1.1 1); 2.7858 (1.44); 2.7809 (1.23); 2.7659 (1.21);

2,4,6-trimethyl- 2.5424 (3.52); 2.5075 (3.25); 2.5031 (4.33); 2.4989 (3.39); 2.3006 (16.00);

12-23 phenyl CH2 CH2 H 2.1828 (8.30); -0.0002 (1.07)

[DMSO], Spektrometer: 399.95MHz 8.3289 (0.63); 8.3153 (1.23); 8.3016 (0.64); 7.6315 (3.39); 7.6172 (3.58); 7.1806 (3.65); 7.1663 (3.47); 6.8748 (2.32); 6.8544 (3.19); 6.8313 (2.61); 6.8267 (2.95); 6.7596 (1.68); 6.7550 (1.56); 6.7393 (1.22); 6.7347 (l .i 5);

3,4-bismethoxy- 3.7316 (16.00); 3.7117 (16.00); 3.4332 (0.90); 3.4165 (1.79); 3.3974 (1.80);

12-24 phenyl CH2 CH2 H 3.3820 (1.00); 3.3407 (7.66); 2.7700 (1.76); 2.7510 (2.68); 2.7331 (1.59);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

8,4262 (2,73); 8,413 (4,89); 8,3996 (2,79); 7,6376 (13,67); 7,6233 (14,65); 7,3506 (7,69); 7,3483 (7,69); 7,338 (8,41 ); 7,3355 (8, 13); 7,2098 (15,14); 7,1955 (14,48); 6,9721 (6,1 ); 6,9635 (9,35); 6,9596 (6,31 ); 6,9509 (8,87); 6,9273 (9,83); 6,9205 (6,8); 3,4749 (4,72); 3,4571 (10,55); 3,4423 (10,87); 3,4245 (5,66); 3,3326 (27,99); 3,0595 (9,29); 3,0414 (16); 3,0234 (8); 2,5408 (9,54); 2,5056 (22,54); 2,5013 (29,54); 2,497 (22,77); -0,0002 (0,5)

12-38 3-thienyl CH2 CH2 - H

12-39 2-furyl CH2 CH2 - H

12-40 3-furyl CH2 CH2 - H

12-41 phenyl CH2 CH2 CH(CH3) H

12-42 phenyl CH2 CH2 CH2 H

12-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

12-44 4-t-butyl-phenyl CH2 CH2 CH2 H

12-45 4-methyl-phenyl CH2 CH2 CH2 H

12-46 phenyl CH2 CH2 CH(CH2CH3) H

12-47 2-methoxy-phenyl CH2 CH2 CH2 H

12-48 2-methyl-phenyl CH2 CH2 CH2 H

12-49 3 -methyl-phenyl CH2 CH2 CH2 H

12-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 12-51 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,3439 (3,57); 8,3309 (6,36); 8,3178 (3,69); 7,6616 (0,33); 7,6471 (0,66); 7,634 (13,3); 7,6212 (13,4); 7,6198 (14,21 ); 7,3509 (1 ,47); 7,333 (4,06); 7,3131 (6,87); 7,2937 (4,81 ); 7,2758 (2,27); 7,2618 (0,44); 7, 197 (15,35); 7,1827 (14,55); 7,1425 (0,32); 7,1208 (0,5); 7, 1009 (1 ,56); 7,0882 (10,47); 7,0686 (16); 7,0493 (8,79); 7,0349 (1 ,36); 6,5486 (0,63); 3,3361 (29,78); 3,2664 (5,24); 3,2496 (1 1 ,89); 3,2332 (12,1 1 ); 3,2164 (5,54); 2,7079 (7,58); 2,6887 (12,66); 2,6694 (8,51 ); 2,5446 (9,47); 2,5056 (37,84); 1 ,7988 (2,81 ); 1 ,7801 (7,74); 1 ,7614 (10,65); 1 ,7426 (7,42); 1 ,7243 (2,52); -0,0002 (0,54)

12-51 2,6-difluor-phenyl CH2 CH2 CH2 H

12-52 4-chlor-phenyl CH2 CH2 CH2 H

12-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

12-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

12-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

12-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

12-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

3 -trifluormethyl-

12-58 phenyl CH2 CH2 CH(CH3) H

12-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

12-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

12-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

12-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

12-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

4-trifluormethyl-

12-64 phenyl CH2 CH2 CH(CH3) H

12-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

12-66 4-phenoxy-phenyl CH2 CH2 CH2 H

12-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

12-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

12-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

2-difluormethoxy-

12-70 phenyl CH2 CH2 CH(CH3) H

12-71 4-methoxy-phenyl CH2 CH2 CH2 H

12-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

12-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

12-74 4-fluor-phenyl CH2 CH2 CH2 H

12-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

12-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

12-77 2-chlor-phenyl CH2 CH2 CH2 H

12-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl WO-A 2007/060164

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr. 12-79, Solvent: [DMSO], Spektrometer: 399.95MHz 8,3298 (2,96); 8,3169 (5,26); 8,3042 (3,1 ); 7,6325 (14,47); 7,6183 (15,49); 7,321 1 (8,42); 7,3186 (7,65); 7,3083 (9,3); 7,3058 (8,14); 7,2108 (16); 7, 1966 (15,18); 6,9528 (6,49); 6,9442 (9,31 ); 6,9403 (6,93); 6,9316 (8,34); 6,8914 (10,08); 6,8833 (8,16); 3,328 (186,81 ); 3,2777 (5,37); 3,2609 (12,9); 3,2458 (13,23); 3,229 (5,65); 2,8831 (9,1 1 ); 2,864 (15,57); 2,8449 (9,91 ); 2,6708 (0,98); 2,5408 (3,1 1 ); 2,5058 (106,56); 2,5016 (136,82); 2,4976 (105,49); 2,3285 (0,9); 1 ,8804 (2,82); 1 ,8625 (8,73); 1 ,8438 (1 1 ,62); 1 ,8255 (8,42); 1 ,8075

12-79 2-thienyl CH2 CH2 CH2 H (2,56); -0,0002 (1 ,36)

Verbindung Nr. 12-80, Solvent: [DMSO], Spektrometer: 399.95MHz 8,432 (1 ,82); 8,4184 (3,38); 8,4047 (1 ,79); 8,3155 (1 ,88); 7,6414 (15,17); 7,6271 (16); 7,3751 (14,36); 7,3713 (14,43); 7,3638 (0,37); 7,2076 (0,36); 7,1958 (15,71 ); 7,1815 (14,83); 6,9256 (9,98); 6,9239 (8,92); 6,922 (9,73); 3,4729 (3,5); 3,4555 (8,91 ); 3,441 (9,18); 3,4239 (4,02); 3,3222 (44,18); 3,0393 (0,33); 3,0233 (6,68); 3,0058 (12,63); 2,9887 (5,62); 2,6753 (0,39); 2,6707 (0,53); 2,6661 (0,38); 2,5239 (1 ,8); 2,5191 (2,81 ); 2,5106 (32,21 ); 2,5062 (64,19); 2,5016 (83,82); 2,497 (59,36); 2,4924 (27,72); 2,3329 (0,4); 2,3283 (0,55); 2,3237 (0,41 ); 1 ,9887 (0,99); 1 ,3357 (0,35); 1 ,2494 (0,43); 1 ,1749 (0,53); 0, 1459 (0,33); 0,008 (2,83); -0,0002 (78,68); -0,0085 (2,37); -0,1496

12-80 5-chlor-2-thienyl CH2 CH2 H (0,33)

Verbindung Nr. 12-81 , Solvent: [DMSO], Spektrometer: 601.6MHz 8,4249 (1 ,78); 8,4158 (3,3); 8,4066 (1 ,74); 7,639 (15,4); 7,6295 (16); 7,3751 (13,88); 7,3725 (13,92); 7,1923 (15,77); 7,1828 (15,35); 6,9252 (9,32); 6,924 (8,25); 6,9228 (9,13); 3,464 (3,67); 3,4524 (8,92); 3,4428 (9,08); 3,4314 (4,07); 3,3535 (0,49); 3,3256 (836,97); 3,3031 (0,84); 3,0173 (5,99); 3,0056 (1 1 ,69); 2,9947 (5,41 ); 2,6531 (1 ,58); 2,6192 (0,57); 2,6162 (1 ,19); 2,6131 (1 ,66); 2,61 (1 ,22); 2,607 (0,58); 2,5407 (486,63); 2,5224 (3,63); 2,5193 (4,8); 2,5161 (5,78); 2,5075 (92,82); 2,5044 (192,64); 2,5014 (263,85); 2,4983 (189,46); 2,4953 (88,15); 2,4245 (1 ,58); 2,3916 (0,56); 2,3886 (1 ,18); 2,3855 (1 ,63); 2,3825 (1 , 15); 2,3795 (0,51 ); 2,0735 (0,57); 0,0053 (0,56); -

12-81 4-chlor-2-thienyl CH2 CH2 H 0,0002 (15,95); -0,0057 (0,45)

Verbindung Nr. 12-82, Solvent: [DMSO], Spektrometer: 399.95MHz 8,2813 (0,73); 8,2674 (1 ,4); 8,2535 (0,75); 7,8316 (3,37); 7,8264 (3,35); 7,1794 (4,23); 7, 157 (4,61 ); 7, 1488 (0,56); 6,8767 (3,52); 6,8715 (3,44); 6,7524 (4,57); 6,7299 (4,09); 3,4651 (1 ,31 ); 3,4485 (3,06); 3,4314 (2,35); 3,3556 (1 ,46); 3,3279 (46,87); 2,9073 (16);

12-82 4-chlor-phenyl N(CH3) CH2 CH2 H 2,5415 (20,17); 2,5064 (30,6); 2,5024 (38,46); -0,0002 (4,87)

Verbindung Nr. 12-83, Solvent: [DMSO], Spektrometer: 399.95MHz 8,3165 (0,38); 8, 1187 (2,84); 8,099 (2,84); 7,8058 (6,33); 7,7928 (6,56);

3 -(trifluormethyl)- 7,785 (1 , 18); 7,5428 (1 ,9); 7,5232 (4,2); 7,5036 (2,82); 7,4898 (0,46);

12-83 phenyl 0 CH2 CH(CH2CH3) H 7,3461 (0,34); 7,2982 (6,29); 7,2784 (5, 13); 7,2686 (8, 1 1 ); 7, 1795 (6,69);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7,1665 (6,51); 7,15 (0,77); 4,2211 (0,85); 4,2081 (1,31); 4,2001 (1,72); 4,1867 (2,03); 4,1687 (3,2); 4,1455 (4,52); 4,1306 (3,15); 4,1162 (3,62); 4,1033 (3,3); 4,0927 (2,02); 4,0795 (1,14); 3,3274 (85,66); 2,6715 (0,48); 2,5421 (8,14); 2,5025 (75,15); 2,4986 (60,82); 2,329 (0,51); 1,7771 (0,84); 1,7587 (1,27); 1,7434 (1,92); 1,7301 (1,65); 1,7247 (1,75); 1,712 (1,37); 1.6939 (0,56); 1,6778 (0,34); 1.6605 (0,5); 1,6457 (1.3); 1.6263 (1,94); 1,6077 (1,72); 1,5919 (1,41); 1.5727 (0,89); 0,9905 (8,04); 0.9722 (16); 0,9536 (7,45); 0,9419 (1,2); -0,0002 (9,15); -0,0018 (7,67)

Tabelle 13

Verbindungen der Formel 1-13

1-13

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

13-1 3 -methyl-2-thienyl CH2 CH2 - H WO-A 2006/108791

Verbindung Nr. 13-2, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2987 (1,89); 8,2849 (3,6); 8,271 (1,85); 7,7558 (15,43); 7,7487 (0,67); 7,7421 (16); 7,5825 (0,33); 7,5726 (10,55); 7,5673 (11,03); 7,4427 (6,72); 7,422 (13,06); 7,4149 (0,91); 7,3841 (9,11); 7,3787 (8,54); 7,3634 (4,59); 7,3581 (4,56); 7,1268 (15,9); 7,1131 (15,34); 3,5119 (1,39); 3,4113 (0,38); 3,3318

13-2 2,4-dichlor-phenyl CH2 CH2 CH2 H (475,8); 3,2911 (0,54); 3,2673 (3,24); 3,2503

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

(7,5); 3,2354 (7,53); 3,2184 (3,21 ); 2,7694 (5,51 ); 2,7505 (6,8); 2,7307 (5,96); 2,7121 (0,34); 2,6805 (0,44); 2,6759 (0,89); 2,6714 (1 ,21 ); 2,6667 (0,9); 2,662 (0,41 ); 2,5416 (59,45); 2,5247 (3,74); 2,5199 (5,99); 2,51 14 (67,36); 2,5069 (1 34,03); 2,5022 (177,24); 2,4976 (127,83); 2,4931 (59,8); 2,3382 (0,42); 2,3336 (0,87); 2,329 (1 , 19); 2,3244 (0,83); 2,3198 (0,37); 2, 103 (0,34); 1 ,821 (1 ,61 ); 1 ,8031 (4,28); 1 ,7842 (5,47); 1 ,7655 (4, 13); 1 ,7475 (1 ,44); 0,008 (0,69); -0,0002 (20,21 ); -0,0085 (0,54)

Verbindung Nr. 1 3-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3053 (1 ,38); 8,2916 (2,62); 8,2776 (1 ,36); 7,749 (1 1 ,36); 7,7418 (0,44); 7,7353 (1 1 ,67); 7,3674 (0,94); 7,3612 (8,6); 7,3562 (3,01 ); 7,3452 (4,05); 7,34 (16); 7,334 (2, 14); 7,294 (2,07); 7,2882 (1 3,58); 7,283 (3,52); 7,2718 (2,81 ); 7,267 (7,48); 7,2609 (0,8); 7,0851 (1 1 ,42); 7,0714 (1 1 ,09); 3,51 1 7 (0,89); 3,4442 (2,49); 3,4269 (4,88); 3,4122 (4,9); 3,3938 (2,78); 3,3314 (322,94); 2,8373 (4,56); 2,819 (7,6); 2,801 1 (4,04); 2,6756 (0,6); 2,671 (0,8); 2,6665 (0,57); 2,5413 (10,27); 2,5244 (2,31 ); 2,5196 (3,74); 2,51 1 1 (44,51 ); 2,5066 (88,79); 2,5019 (1 1 7,47); 2,4973 (84,7); 2,4928 (39,68); 2,3333 (0,56); 2,3287 (0,77); 2,3241 (0,53); 0,008 (0,56); -

13-3 4-chlor-phenyl CH2 CH2 H 0,0002 (16,55); -0,0086 (0,45)

13-4 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/060166

13-5 4-chlor-phenyl CH(0CH3) CH(CH3) - H

13-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

Verbindung Nr. 1 3-7, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2561 (1 ,25); 8,2419 (2,48); 8,2274 (1 ,26); 7,7295 (9,88); 7,7223 (0,4); 7,7158 (10,23); 7,3705 (0,75); 7,3644 (7, 1 ); 7,3594 (2,54); 7,3483 (3,46); 7,3431 (14,93); 7,3373 (2,09); 7,3069 (2,02); 7,3012 (1 3,53); 7,296 (3,31 ); 7,2848 (2,4); 7,2799 (6,74); 7,2738 (0,76); 7,0236 (10,41 ); 7,0099 (10, 16); 3,5121 (0,7);

13-7 4-chlor-phenyl CH(CH3) CH2 H 3,3878 (0,39); 3,3728 (0,55); 3,3693 (0,62);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

3,3548 (2,68); 3,3289 (97,66); 3,3107 (3,04); 3,2961 (0,58); 3,2923 (0,6); 3,278 (0,51); 3,0683 (1,24); 3,0504 (2,52); 3,0326 (2,42); 3,0148 (1,11); 2,6711 (0,35); 2,5414 (15,89); 2,5245 (0,99); 2,5198 (1,51); 2,5111 (19,8); 2,5066 (40,45); 2,502 (54,26); 2,4974 (39,63); 2,4928 (18,95); 2,3288 (0,35); 1,2409 (16); 1,2234 (15,75); -0,0002 (6,01)

Verbindung Nr.13-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3017 (1,41); 8,2873 (2,82); 8,2731 (1,39); 7,7292 (10,7); 7,7221 (0,46); 7,7155 (11,01) 7,5578 (8,3); 7,5524 (8,74); 7,4785 (4,97); 7,4573 (9,57); 7,419 (5,79); 7,4135 (5,26); 7,3979 (2,92); 7,3924 (2,8); 7,0318 (10,37): 7,018 (10,13); 3,5497 (1,06); 3,5323 (2,47) 3,5146 (3,01); 3,4978 (1,64); 3,4833 (1,57) 3,4689 (1,35); 3,4514 (2,73); 3,4361 (2,61) 3,4191 (1,56); 3,4062 (1,85); 3,3917 (2,38) 3,3889 (1,99); 3,3739 (2,58); 3,3592 (1,24) 3,3563 (1,18); 3,333 (68,37); 2,5427 (49,66) 2,5255 (0,6); 2,5209 (0,94); 2,5125 (11,53); 2,508 (23,26); 2,5033 (30,98); 2,4987 (22,51); 2,4942 (10,68); 1,2328(16); 1,2158

13-8 2,4-dichlor-phenyl CH(CH3) CH2 H (15,75); -0,0002 (3,19)

Verbindung Nr.13-9, Solvent: [DMSO], Spektrometer: 399.95MHz

8,1044 (2,51); 8,0839 (2,54); 7,7377 (10,6) 7,7305 (0,42); 7,724 (10,89); 7,3504 (0,89) 7,3443 (7,7); 7,3393 (2,67); 7,3283 (3,68); 7,3231 (14,88); 7,3172 (1,94); 7,2799 (2); 7,2741 (12,71); 7,269 (3,21); 7,2578 (2,58) 7,2529 (6,83); 7,247 (0,75); 7,0448 (10,83) 7,0311 (10,47); 4,167 (0,62); 4,1478 (1,31) 4,1309 (1,9); 4,1142 (1,38); 4,0949 (0,65); 3,5115 (1 ,35); 3,3668 (0,57); 3,3303 (363,77); 3,3147 (1,88); 3,2993 (0,51); 2,8512 (1,59); 2,8319 (1,56); 2,8176 (2,83); 2,7983 (2,77); 2,7488 (2,84); 2,733 (2,9); 2,7152 (1,62); 2,6993 (1,5); 2,68 (0,33); 2,6755 (0,67); 2,6709 (0,91); 2,6663 (0,67); 2,5411 (3,77); 2,5243 (2,77); 2,5195 (4,46); 2,511 (50,16); 2,5064 (100,33); 2,5018 (133,07); 2,4972 (95,94); 2,4926 (44,84);

13-9 4-chlor-phenyl CH2 CH(CH3) H 2,3332 (0,64); 2,3286 (0,88); 2,324 (0,62);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

7,3695 (1 ,74); 7,3636 (1 ,57); 7,3479 (1 ,29); 7,342 (1 , 18); 6,9686 (3,36); 6,9549 (3,29); 3,7487 (3, 12); 3,7328 (3,06); 3,3337 (20,32); 2,5423 (16,32); 2,5121 (3,68); 2,5077 (6,98); 2,5031 (9,01 ); 2,4985 (6,55); 2,4941 (3, 16); 1 ,4696 (16); -0,0002 (0,69)

Verbindung Nr. 1 3-13, Solvent: [DMSO], Spektrometer: 399.95MHz

8,361 1 (1 ,83); 8,3468 (3,5); 8,3328 (1 ,79); 7,7495 (15,4); 7,7421 (0,6); 7,7357 (16); 7,4425 (4,95); 7,4386 (3,91 ); 7,424 (7,06); 7,4194 (6,32); 7,3805 (3,65); 7,3752 (4,51 ); 7,3619 (4,8); 7,3572 (6, 14); 7,31 14 (2,22); 7,3073 (2,84); 7,2931 (6,69); 7,2889 (6,34); 7,2756 (10,83); 7,2701 (9, 19); 7,2568 (5,39); 7,2517 (5,07); 7,2382 (1 ,86); 7,2334 (1 ,52); 7, 1032 (15,46); 7,0894 (15,02); 3,51 17 (1 , 17); 3,4786 (3,37); 3,461 7 (6,34); 3,4468 (6,04); 3,4432 (6,06); 3,4281 (3,75); 3,4108 (0,42); 3,3331 (448,32); 3,2697 (0,34); 2,9789 (6,53); 2,9602 (9,91 ); 2,9426 (5,64); 2,6804 (0,34); 2,6758 (0,7); 2,671 1 (0,96); 2,6665 (0,68); 2,5414 (52,44); 2,5245 (2,8); 2,5198 (4,51 ); 2,51 12 (52,97); 2,5067 (106,54); 2,502 (141 ,67); 2,4974 (102,33); 2,4929 (47,92); 2,3334 (0,67); 2,3288 (0,93);

13-13 2-chlor-phenyl CH2 CH2 H 2,3242 (0,65); -0,0002 (3,71 )

Verbindung Nr. 1 3-14, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2994 (1 ,97); 8,2855 (3,84); 8,2716 (1 ,98); 7,7536 (14, 19); 7,7463 (0,6); 7,7399 (14,7); 7,5549 (10,77); 7,5445 (0,53); 7,5341 (16); 7,5272 (10,25); 7,2648 (5,81 ); 7,2596 (5,62); 7,2442 (5,04); 7,2391 (4,96); 7,0699 (15,43); 7,0561 (15,03); 3,5136 (0,7); 3,4695 (3,22); 3,4522 (7,96); 3,4375 (8, 1 ); 3,4203 (3,51 ); 3,3359 (88,36); 2,8542 (6,07); 2,8368 (12,01 ); 2,8194 (5,46); 2,5431 (44,95); 2,5263 (0,6); 2,5214 (0,96); 2,5128 (1 3, 1 3); 2,5083 (26,83); 2,5037 (36,02); 2,4991

13-14 3 ,4-dichlor-phenyl CH2 CH2 H (26,35); 2,4946 ( 12,64); -0,0002 (3,02)

Verbindung Nr. 13-15, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2988 (1 ,57); 8,2851 (2,98); 8,271 3 (1 ,55);

13-15 3,5- dichlor-pheny 1 CH2 CH2 H 7,7573 (8,92); 7,7436 (9, 16); 7,4369 (3,65);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

7,4323 (7,01); 7,4275 (4,12); 7,329 (16); 7,3243 (14,78); 7,056 (9,44); 7,0423 (9,26) 3,5115 (1,37); 3,4764 (2,57); 3,4593 (6,18) 3,4446 (6,44); 3,4276 (2,74); 3,4112 (0,53) 3,3849 (0,75); 3,3336 (504,34); 2,8637 (4,44); 2,8465 (8,92); 2,8293 (3,97); 2,6755 (0,84); 2,6711 (1,11); 2,6666 (0,82); 2,5415 (20,02); 2,5065 (125,79); 2,502 (162,85); 2,4975 (120,54); 2,4932 (59,35); 2,3333 (0,79); 2,3288 (1 ,07); 2,3243 (0,75); -0,0002

Verbindung Nr.13-16, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3173 (1 ,98); 8,3037 (3,72); 8,2901 (2); 7,7524 (13,05); 7,7387 (13,54); 7,361 (0,39); 7,3476 (3,48); 7,3397 (1,02); 7,3274 (16); 7,3221 (6,31); 7,3092 (8,47); 7,2883 (0,72); 7,2797 (4,31); 7,2767 (6,34); 7,2718 (4,72); 7,26 (2,46); 7,255 (2,92); 7,2518 (2,01); 7,2297 (6,42); 7,2141 (3,21); 7,2109 (4,46); 7,0878 (0,83); 7,081 (13,81); 7,074 (1,01); 7,0673 (13,43); 3,5129 (0,64); 3,4647 (3,49); 3,4474 (7,27); 3,4326 (7,23); 3,4145 (4,03); 3,3362 (80,45); 2,8591 (6,55); 2,841 (11,42); 2,8231 (5,99); 2,5422 (35,15); 2,5251 (0,65); 2,5118 (13,37); 2,5073 (26,75); 2,5028 (35,56); 2,4982 (26,02); 2,4937 (12,5); -

13-16 3-chlor-phenyl CH2 CH2 H 0,0002(3,04)

Verbindung Nr.13-17, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3625 (2,93); 8,3491 (5,38); 8,3353 (2,96); 7,7494 (15,29); 7,7357 (16); 7,3475 (3,34); 7,3323 (5,91); 7,3283 (6,81); 7,3092 (4,07); 7,3003 (1,66); 7,296 (1,56); 7,2819 (3,83); 7,2797 (3,82); 7,2672 (3,89); 7,2615 (4,95); 7,2478 (2,7); 7,2437 (2,33); 7,1781 (5,29); 7,1571 (11,37); 7,1407 (9,26); 7,1379 (9,6); 7,1224 (4); 7,1195 (3,76); 7,1099 (0,46); 7,0953 (15,7); 7,0816 (15,32); 3,513 (0,71); 3,4573 (4,34); 3,4402 (9,63); 3,4222 (9,61); 3,4063 (4,88); 3,3353 (109,15); 2,8859 (7,7); 2,8676 (13,14); 2,8495 (6,88); 2,6718 (0,35); 2,5421 (19,64); 2,5072 (40,84); 2,5028 (52,67); 2,4984 (41 ,42); 2,3296 (0,33); -

13-17 2-fluor-phenyl CH2 CH2 H 0,0002 (3,3)

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

Verbindung Nr. 13-18, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4194 (1 ,58); 8,4049 (3,04); 8,3906 (1 ,56); 7,7512 (1 1 ,16); 7,7374 (1 1 ,56); 7,3616 (0,9); 7,3447 (2,04); 7,3407 (1 ,77); 7,3238 (3,83); 7,3066 (1 ,94); 7,303 (2,44); 7,2862 (1 , 14); 7, 1048 (0,53); 7,1004 (0,75); 7,0883 (5,54); 7,0792 (13,16); 7,0655 (16); 7,0573 (1 ,28); 7,0485 (4,48); 7,0358 (0,61 ); 3,5123 (1 ,02); 3,4222 (2,6); 3,4056 (5,96); 3,3882 (5,72); 3,3717 (3,02); 3,3344 (184,38); 2,8991 (3,93); 2,8812 (7,01 ); 2,8636 (3,47); 2,6763 (0,33); 2,6717 (0,46); 2,5419 (12,12); 2,525 (1 ,42); 2,5202 (2,3); 2,51 17 (26,3); 2,5072 (51 ,9); 2,5026 (68,37); 2,498 (49,52); 2,4935 (23,41 ); 2,334 (0,33); 2,3293 (0,44); -0,0002

13-18 2,6-difluor-phenyl CH2 CH2 H (4,55)

Verbindung Nr. 13-19, Solvent: [DMSO], Spektrometer: 399.95MHz

8,43 (1 ,73); 8,4158 (3,4); 8,4015 (1 ,77); 7,7507 (8,75); 7,737 (9, 15); 7,4659 (12,07); 7,4457 (16); 7,3012 (5,39); 7,282 (6,3); 7,2803 (5,6); 7,2609 (3,54); 7,1251 (9,59); 7, 1 1 13 (9,36); 3,4641 (2,26); 3,4477 (5,74); 3,4292 (5,71 ); 3,4138 (2,96); 3,3323 (41 ,62); 3, 176 (5,34); 3,1574 (8,32); 3,1403 (4,23); 2,5429 (1 , 1 ); 2,5081 (24,3); 2,5036 (31 ,79);

13-19 2,6-dichlor-phenyl CH2 CH2 H 2,4992 (24,46); -0,0002 (3,6)

Verbindung Nr. 13-20, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3278 (2, 13); 8,3141 (3,93); 8,3002 (2,01 ); 7,762 (0,54); 7,7504 (15,29); 7,7367 (15,65); 7,6712 (0,37); 7,6513 (0,47); 7,6 (7,88); 7,5873 (2,74); 7,5809 (3,05); 7,5655 (12,74); 7,5528 (8,63); 7,5425 (2,38); 7,5348 (2,41 ); 7,5165 (1 ,26); 7,4979 (0,46); 7,478 (0,35); 7,0868 (0,61 ); 7,0729 (0,82); 7,0642 (16); 7,0505 (15,64); 3,5139 (0,98); 3,4986 (3,51 ); 3,4813 (7,94); 3,4667 (7,96); 3,4489 (3,95); 3,3328 (77,08); 2,9553 (6,5); 2,9375 (1 1 ,89); 2,9198 (5,72); 2,5427 (55,96); 2,5258 (0,88); 2,521 (1 ,52); 2,5125 (17,59); 2,508 (34,92); 2,5034 (46,06); 2,4988 (33,34); 2,4943

13-20 3 -(trifluormethyl)-phenyl CH2 CH2 H (15,66); -0,0002 (5,77)

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

Verbindung Nr. 13-21 , Solvent: [DMSO], Spektrometer: 399.95MHz

8,345 (2,07); 8,3312 (3,97); 8,3174 (2,05); 7,7521 (15,19); 7,7449 (0,74); 7,7384 (15,59); 7,6713 (9,55); 7,6512 (1 1 ,82); 7,4978 (1 1 ,02); 7,4778 (8,98); 7,0868 (16); 7,073 (15,56); 3,5139 (1 ,01 ); 3,498 (3,41 ); 3,4808 (7,29); 3,4661 (7,13); 3,4479 (3,7); 3,3331 (76,49); 2,9475 (5,5); 2,9296 (9,85); 2,91 17 (4,79); 2,5428 (44,99); 2,5258 (0,91 ); 2,5126 (16,8); 2,5081 (33,52); 2,5034 (44,47); 2,4988 (32,31 ); 2,4943 (15,37); -

13-21 4-(trifluormethyl)-phenyl CH2 CH2 H 0,0002 (6,57)

Verbindung Nr. 13-22, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3703 (0,6); 8,3563 (1 , 15); 8,3423 (0,6); 7,7585 (4,85); 7,7448 (5,06); 7,1827 (0,86); 7, 1753 (1 ,22); 7,1694 (1 ,38); 7,1602 (2,44); 7, 1559 (1 ,67); 7,1472 (2,14); 7,1404 (0,91 ); 7, 1289 (2,83); 7,123 (8,3); 7,1 151 (4,17); 7, 1091 (5,65); 7,102 (1 ,37); 7,0892 (0,34); 3,51 15 (0,38); 3,3955 (1 ,17); 3,3805 (1 ,97); 3,3769 (1 ,69); 3,3719 (1 ,25); 3,3652 (1 ,39); 3,3621 (1 ,63); 3,357 (2,2); 3,3419 (2,94); 3,3299 (102,26); 2,8401 (2,17); 2,825 (1 ,72); 2,8203 (2,41 ); 2,8017 (1 ,92); 2,5409 (25,53); 2,524 (0,91 ); 2,5192 (1 ,47); 2,5107 (16,02); 2,5062 (31 ,84); 2,5016 (42,21 ); 2,4969 (30,62); 2,4924 (14,51 ); 2,325 (16); -0,0002

13-22 2-methyl-phenyl CH2 CH2 H (3,65)

Verbindung Nr. 13-23, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4542 (0,37); 8,4396 (0,75); 8,4253 (0,37); 7,7732 (2,68); 7,7594 (2,77); 7,1638 (2,72); 7, 1499 (2,66); 6,8104 (4); 3,3309 (67,4); 3,2389 (0,49); 3,2244 (0,85); 3,2192 (0,67); 3,2104 (0,84); 3,2038 (0,66); 3,1971 (0,88); 3, 1832 (0,58); 2,81 12 (1 ,04); 2,7979 (0,79); 2,7901 (1 ,01 ); 2,7846 (0,81 ); 2,7703 (0,87); 2,541 (22, 19); 2,5241 (0,58); 2,5194 (0,92); 2,5108 (10,83); 2,5063 (21 ,64); 2,5017 (28,71 ); 2,497 (20,92); 2,4925 (9,98); 2,3028

13-23 2,4,6-trimethyl-phenyl CH2 CH2 H (16); 2,184 (6,91 ); -0,0002 (2,34)

Verbindung Nr. 13-24, Solvent: [DMSO],

13-24 3 ,4-bismethoxy-phenyl CH2 CH2 H Spektrometer: 399.95MHz

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

Spektrometer: 399.95MHz 8,4226 (2,55); 8,4093 (4,92); 8,3959 (2,59) 7,7714 (12,28); 7,7577 (12,83); 7,5717 (10,86); 7,5653 (1 1 ,79); 7,386 (5,53); 7,3795 (5,32); 7,3638 (7,47); 7,3574 (7,31 ); 7,2398 (12,67); 7,21 75 (9,52); 7, 1676 (12,98) 7, 1538 (12,55); 4,2096 (7, 1 7); 4, 1949 (16) 4, 1803 (7,92); 3,6208 (3,98); 3,6065 (1 1 ,08) 3,5923 (10,76); 3,5778 (3,63); 3,3705 (0,32) 3,3316 (159, 1 1 ); 2,7121 (0,38); 2,6762 (0,37); 2,672 (0,5); 2,6673 (0,37); 2,5421 (80, 13); 2,5252 (1 ,63); 2,5072 (55,73) 2,5028 (73,58); 2,4984 (56,36); 2,3683 (0,38); 2,3341 (0,34); 2,3295 (0,47); 2,3253 (0,36); -0,0002 (1 ,71 )

13-32 4-chlor-phenyl CH2 CH2 CH2 H

13-33 4-chlor-phenyl NCH3 CH2 CH2 H

13-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

13-35 4-chlor-phenyl CH(OCH3) CH2 - H

13-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 13-37, Solvent: [DMSO] Spektrometer: 399.95MHz 8,3969 (2,78); 8,3833 (5,22); 8,3696 (2,88) 7,7643 (15,35); 7,7505 (16); 7,3519 (8,28) 7,349 (8,09); 7,3393 (9, 16); 7,3363 (8,55) 7, 1406 (15,8); 7, 1269 (15,34); 6,9738 (6, 19) 6,9652 (9,7); 6,9612 (6,2); 6,9526 (9,38) 6,9326 (9,72); 6,931 (9,7); 6,9246 (6,81 ) 3,4692 (4,45); 3,4515 (9,93); 3,4367 (10, 12) 3,4186 (5,26); 3,3291 (51 ,64); 3,0625 (8,98) 3,0443 (15,33); 3,0262 (7,65); 2,6706 (0,35) 2,5408 (15,47); 2,5058 (38,81 ); 2,5014 (50,88); 2,497 (38,5); -0,0002 (0,99)

13-37 2-thienyl CH2 CH2 H

13-38 3-thienyl CH2 CH2 - H

13-39 2-furyl CH2 CH2 - H

13-40 3-furyl CH2 CH2 - H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

13-41 phenyl CH2 CH2 CH(CH3) H

13-42 phenyl CH2 CH2 CH2 H

13-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

13-44 4-t-butyl-phenyl CH2 CH2 CH2 H

13-45 4-methyl-phenyl CH2 CH2 CH2 H

13-46 phenyl CH2 CH2 CH(CH2CH3) H

13-47 2-methoxy-phenyl CH2 CH2 CH2 H

13-48 2-methyl-phenyl CH2 CH2 CH2 H

13-49 3 -methyl-phenyl CH2 CH2 CH2 H

13-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 13-51 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,2922 (3,17); 8,2786 (5,88); 8,2649 (3,23); 7,7845 (0,37); 7,7707 (0,45); 7,7558 (15,29); 7,7421 (16); 7,3509 (1 ,52); 7,3338 (3,63); 7,3304 (3,4); 7,3131 (6,65); 7,2951 (3,82); 7,2924 (4,41 ); 7,2755 (1 ,93); 7,2133 (0,34); 7, 1995 (0,34); 7,14 (0,51 ); 7,1253 (15,58); 7,1 1 16 (15,3); 7,1021 (1 ,76); 7,0887 (9,35); 7,069 (14,86); 7,0492 (7,93); 7,0356 (1 ,16); 6,5422 (0,68); 3,337 (21 ,45); 3,2628 (4,51 ); 3,2457 (9,72); 3,2291 (9,77); 3,2124 (4,74); 2,712 (6,57); 2,6928 (10,9); 2,6735 (7,35); 2,5448 (10,46); 2,5096 (22,82); 2,5053 (30,14); 2,501 (23,5); 1 ,8059 (2,44); 1 ,7867 (6,52); 1 ,7683 (9,14); 1 ,7494 (6,14); 1 ,7309 (2,16); -0,0002 (0,58)

13-51 2,6-difluor-phenyl CH2 CH2 CH2 H

13-52 4-chlor-phenyl CH2 CH2 CH2 H

13-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

13-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

13-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

13-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

13-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

13-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

13-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

13-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

13-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

13-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

13-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

13-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

13-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

13-66 4-phenoxy-phenyl CH2 CH2 CH2 H

13-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

13-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

13-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

13-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

13-71 4-methoxy-phenyl CH2 CH2 CH2 H

13-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

13-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

13-74 4-fluor-phenyl CH2 CH2 CH2 H

13-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

13-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

13-77 2-chlor-phenyl CH2 CH2 CH2 H

13-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl WO-A 2007/060164

Verbindung Nr. 13-79, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,2788 (2,87); 8,2654 (5,26); 8,252 (2,96);

7,7525 (14,98); 7,7387 (15,7); 7,3199 (7,88);

7,3171 (8,06); 7,3072 (8,7); 7,3044 (8,53);

7, 1374 (16); 7, 1236 (15,6); 6,9537 (6,59);

6,9451 (9,28); 6,941 (6,86); 6,9324 (8,74);

6,8987 (9,21 ); 6,8973 (9,39); 6,8909 (7,3);

3,3332 (29,69); 3,2794 (4,86); 3,2624

(1 1 ,62); 3,2474 (1 1 ,69); 3,2306 (5,2); 2,8959

13-79 2-thienyl CH2 CH2 CH2 H (8,31 ); 2,8768 (14,02); 2,8577 (9,05); 2,5408

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

(18,14); 2,5238 (0,68); 2,5059 (21,46); 2,5015 (28,83); 2,4971 (22,39); 1,8886 (2,63); 1,8706 (7,84); 1,8517(10,41); 1,8335 (7,68); 1,8156 (2,43); -0,0002 (0,53)

Verbindung Nr.13-80, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4106 (1,21); 8,3962 (2,12); 8,3821 (1,17); 8,3165 (8,26); 7,725 (8,06); 7,7113 (8,28); 7,4792 (4,61); 7,4736 (2,06); 7,4631 (3,24); 7,4574 (16); 7,4382 (11,72); 7,4165 (3,66); 6,9354 (8,49); 6,9216 (8,27); 4,0537 (0,76) 4,0387 (0,96); 4,0304 (1 ,28); 4,0153 (1 ,37) 4,0066 (1,02); 3,9918 (0,93); 3,9827 (0,35) 3,8704 (0,88); 3,857 (1,49); 3,843 (1,01); 3,8364 (1,49); 3,823 (2,22); 3,8094 (1,21); 3,7387 (1,21); 3,7225 (1,45); 3,7163 (1,26); 3,7047 (1,39); 3,7003 (1,38); 3,6886 (0,92); 3,6823 (0,86); 3,666 (0,72); 3,3218 (50,2); 3,2981 (3,38); 2,6795 (0,35); 2,6749 (0,67); 2,6706 (0,93); 2,666 (0,67); 2,5238 (3,65); 2,5105 (53,97); 2,5061 (106,26); 2,5015 (138,08); 2,4969 (98,64); 2,4925 (46,97); 2,3328 (0,65); 2,3282 (0,9); 2,3237 (0,64);

13-80 4-chlor-phenyl CH(CF3) CH2 H 0,008 (0,68); -0,0002 (19,32); -0,0085 (0,63)

Verbindung Nr.13-81, Solvent: [DMSO], Spektrometer: 601.6MHz

8,3946 (2,08); 8,3853 (4,02); 8,376 (2,1); 7,7651 (15,61); 7,756 (16); 7,3742 (14,08); 7,3717 (14,19); 7,1256 (15,83); 7,1165 (15,6); 6,9282 (10,18); 6,927 (9,69); 6,9259 (10,09); 3,4591 (3,81); 3,4475 (9,26); 3,4378 (9,49); 3,4263 (4,25); 3,3523 (0,67); 3,3253 (1063,51); 3,3017 (0,95); 3,2969 (0,51); 3,0211 (6,61); 3,0094 (12,8); 2,998 (6); 2,6531 (2,09); 2,6191 (0,74); 2,6161 (1,6); 2,6131 (2,23); 2,61 (1,59); 2,6071 (0,72); 2,5605 (0,47); 2,5407 (617,38); 2,5224 (4,3); 2,5193 (5,21); 2,5162 (5,18); 2,5074 (120,61); 2,5044 (259,43); 2,5013 (360,76); 2,4983 (262,2); 2,4953 (122,46); 2,4246 (2,1); 2,3916 (0,73); 2,3886 (1,6); 2,3855 (2,23); 2,3825 (1 ,59); 2,3795 (0,73); 2,0735 (1,11); 0,0052 (0,55); -0,0002 (20,16); -

13-81 4-chlor-2-thienyl CH2 CH2 H 0,0057 (0,62)

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

Verbindung Nr. 13-82, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3356 (0,74); 8,3212 (1 ,42); 8,3074 (0,73); 7,7465 (3,22); 7,7328 (3,28); 7,1828 (4,27); 7, 1603 (4,59); 7,1519 (0,5); 7,0478 (3,52); 7,0341 (3,4); 6,7577 (4,58); 6,735 (4,07); 3,49 (1 ,35); 3,4733 (3,17); 3,4567 (2,25); 3,3732 (1 ,34); 3,3578 (2,76); 3,3283 (54,15); 2,9194 (16); 2,5412 (18,68); 2,5065 (26,77);

13-82 4-chlor-phenyl N(CH3) CH2 CH2 H 2,5022 (33,81 ); 2,499 (25,6); -0,0002 (4,41 )

Verbindung Nr. 13-83, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3322 (1 ,93); 8,3184 (3,8); 8,3047 (1 ,91 ); 7,7488 (13,18); 7,735 (13,59); 7,3986 (1 ,12); 7,3918 (10,13); 7,3869 (3,75); 7,3753 (4,63); 7,3702 (16); 7,3636 (2,05); 7,2969 (10,34); 7,2771 (6,77); 7,0854 (13,36); 7,0716 (13,06); 5,7561 (1 ,42); 3,4657 (2,96); 3,4486

(6.08) ; 3,4336 (5,93); 3,4152 (3,3); 3,3257 (74,47); 2,8816 (5,71 ); 2,8632 (9,52); 2,8453

(5.09) ; 2,676 (0,34); 2,6713 (0,46); 2,6667 (0,34); 2,5417 (7,2); 2,5246 (1 ,25); 2,51 13 (25,89); 2,5068 (51 ,79); 2,5022 (68,85); 2,4977 (50,2); 2,4932 (23,97); 2,3336 (0,33); 2,329 (0,44); 0,008 (1 ,53); -0,0002 (45,08); -

13-83 4-(Trifluormethyoxy)-phenyl CH2 CH2 H 0,0085 (1 ,45)

Tabelle 14

Verbindungen der Formel 1-14

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

14-1 3 -methyl-2-thienyl CH2 CH2 - H

[DMSO], Spektrometer: 399.95MH2 8.1005 (0.59); 8.0862 (1.15); 8.0720 (0.59); 7.5886 (2.50); 7.5837 (2.62); 7.4979 (3.01) 7.4929 (3.05); 7.3827 (0.84); 7.3776 (0.71); 7.3620 (2.87); 7.3570 (3.02); 7.3454 (4.17) 7.3247 (1.15); 6.7737 (2.91); 6.7687 (2.89); 3.4388 (0.87); 3.4219 (1.99); 3.4063 (1.93) 3.3887 (0.99); 3.3344 (14.10); 2.9293 (1.87); 2.91 12 (3.15); 2.8936 (1.63); 2.5257 (0.50); 2.5209 (0.78); 2.5122 (9.39); 2.5078 (18.89); 2.5033 (24.71); 2.4987 (17.98)

14-2 2,4-dichlor-phenyl CH2 CH2 CH2 H 2.4942 (8.73); 2.4740 (16.00); 0.0080 (0.32); -0.0002 (9.56); -0.0085 (0.34)

14-3 4-chlor-phenyl CH2 CH2 - H US 20090163545

14-4 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/060166

[DMSO], Spektrometer: 399.95MH2 7.7853 (1.01); 7.7637 (1.03); 7.6221 (0.82); 7.6019 (0.84); 7.4943 (2.12); 7.4892 (2.18) 7.4713 (2.63); 7.4663 (2.66); 7.4317 (2.74); 7.4270 (0.88); 7.4152 (1.02); 7.4106 (3.89) 7.4044 (3.22); 7.3997 (1.00); 7.3881 (1.22); 7.3832 (4.95); 7.3775 (0.67); 7.3287 (0.65) 7.3232 (4.39); 7.3184 (1.19); 7.3065 (0.92); 7.3021 (2.62); 7.2728 (0.41); 7.2669 (3.21) 7.2623 (0.95); 7.2502 (0.84); 7.2458 (2.52); 6.8700 (1.95); 6.8650 (1.93); 6.7930 (2.44) 6.7880 (2.42); 4.3047 (1.21); 4.2893 (1.71); 4.2345 (2.04); 4.2182 (2.54); 4.1982 (0.55) 4.1819 (0.33); 4.0897 (0.49); 4.0731 (0.75); 4.0684 (0.57); 4.0564 (0.52); 4.0516 (0.75) 4.0350 (0.45); 3.3333 (70.82); 3.1727 (16.00); 3.1476 (13.43); 2.7121 (0.33); 2.5422 (81.19); 2.5255 (0.60); 2.5206 (0.77); 2.51 19 (1 1.03); 2.5074 (22.78); 2.5028 (30.62) 2.4982 (22.57); 2.4937 (10.85); 2.4687 (10.78); 2.3951 (13.43); 2.3683 (0.38); 1.1356 (5.61); 1.1187 (5.61); 0.9433 (4.40); 0.9262 (4.39); 0.0080 (0.50); -0.0002 (16.90);

14-5 4-chlor-phenyl CH(0CH3) CH(CH3) H 0.0085 (0.52)

14-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MH2 8.0032 (0.58); 7.9889 (1.14); 7.9746 (0.59); 7.4821 (3.03); 7.4772 (3.07); 7.3650 (0.39) 7.3588 (3.39); 7.3540 (1.19); 7.3426 (1.57); 7.3376 (5.86); 7.3315 (0.80); 7.2828 (0.83) 7.2769 (5.47); 7.2720 (1.53); 7.2604 (1.20); 7.2557 (3.30); 7.2497 (0.39); 6.7627 (2.99) 6.7577 (2.94); 3.3647 (0.35); 3.3337 (42.38); 3.3139 (1.33); 3.3060 (0.98); 3.2984 (1.08); 3.2917 (1.05); 3.2877 (1.03); 3.2732 (1.17); 3.2547 (0.36); 3.0451 (0.56); 3.0272 (1.12); 3.0094 (1.07); 2.9915 (0.50); 2.5421 (55.53); 2.5252 (0.38); 2.5205 (0.55) 2.51 19 (7.47); 2.5074 (15.12); 2.5028 (20.09); 2.4982 (14.83); 2.4938 (7.16); 2.452C

14-7 4-chlor-phenyl CH(CH3) CH2 H (16.00); 1.1981 (6.91); 1.1807 (6.81); 0.0080 (0.35); -0.0002 (10.15)

[DMSO], Spektrometer: 399.95MH2 8.0329 (0.65); 8.0186 (1.30); 8.0043 (0.65); 7.5550 (2.99); 7.5499 (3.01); 7.4798 (3.22) 7.4748 (3.12); 7.4572 (1.53); 7.4361 (4.23); 7.4173 (2.70); 7.4121 (2.37); 7.3962 (0.91) 7.3910 (0.87); 6.7579 (3.17); 6.7529 (2.98); 3.5198 (0.49); 3.5023 (1.12); 3.4849 (1.26) 3.4676 (0.72); 3.4452 (0.46); 3.4303 (0.46); 3.4127 (1.19); 3.3971 (1.29); 3.3860 (1.13) 3.3803 (0.95); 3.3715 (1.25); 3.3536 (1.29); 3.3333 (48.84); 2.5426 (52.28); 2.5257 (0.44); 2.51 19 (8.88); 2.5076 (16.98); 2.5031 (21.92); 2.4986 (16.10); 2.4942 (7.74) 2.4485 (16.00); 1.1873 (6.96); 1.1702 (6.84); 0.0079 (0.41); -0.0002 (10.74); -0.0085

14-8 2,4-dichlor-phenyl CH(CH3) CH2 H (0.34)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

14-9 4-chlor-phenyl CH2 CH(CH3) - H WO-A 2007/060164

[DMSO], Spektrometer: 399.95MHz 7.8107 (1.22); 7.7892 (1.24); 7.5607 (2.45); 7.5563 (2.41); 7.4908 (3.01); 7.4858 (3.03); 7.3656 (0.60); 7.3450 (4.88); 7.3418 (4.10); 7.3369 (3.10); 7.3207 (0.40); 7.3162 (0.48); 6.8160 (3.01); 6.81 10 (2.94); 4.2915 (0.59); 4.2741 (0.79); 4.2537 (0.56); 3.3317 (127.65); 2.8915 (3.24); 2.8761 (2.1 1); 2.8712 (2.06); 2.6714 (0.36); 2.5416 (4.90); 2.5246 (0.96); 2.51 11 (20.57); 2.5068 (39.98); 2.5023 (52.16); 2.4978 (38.47); 2.4934 (18.78); 2.4161 (16.00); 2.3291 (0.34); 1.1619 (6.39); 1.1453 (6.35); 0.0078 (0.58); -

14-10 2,4-dichlor-phenyl CH2 CH(CH3) H 0.0002 (15.16); -0.0084 (0.50)

[DMSO], Spektrometer: 399.95MHz 7.7450 (0.40); 7.7293 (0.81); 7.7135 (0.40); 7.4834 (2.27); 7.4784 (2.28); 7.4241 (2.24); 7.4188 (0.82); 7.4077 (1.13); 7.4022 (4.69); 7.3959 (0.67); 7.3673 (0.65); 7.3610 (4.70); 7.3555 (1.09); 7.3444 (0.81); 7.3391 (2.25); 6.7966 (2.18); 6.7916 (2.13); 3.3752 (2.86); 3.3592 (2.87); 3.3335 (29.94); 2.5422 (39.05); 2.5202 (0.37); 2.51 18 (5.39); 2.5073 (10.92); 2.5027 (14.51); 2.4982 (10.65); 2.4937 (5.1 1); 2.4261 (1 1.72); 1.2582 (16.00);

14-11 4-chlor-phenyl C(CH3)2 CH2 H -0.0002 (7.76)

[DMSO], Spektrometer: 399.95MHz 7.7346 (0.44); 7.7188 (0.91); 7.7029 (0.44); 7.5332 (2.44); 7.5274 (2.60); 7.4699 (2.42); 7.4648 (2.45); 7.4544 (1.64); 7.4328 (2.53); 7.3640 (1.71); 7.3582 (1.61); 7.3425 (1.10); 7.3366 (1.06); 6.7625 (2.29); 6.7575 (2.27); 3.7172 (2.85); 3.7011 (2.82); 3.3342 (36.20); 2.5425 (34.60); 2.5208 (0.40); 2.5122 (5.45); 2.5077 (1 1.08); 2.5031 (14.82);

14-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 2.4985 (10.91); 2.4941 (5.24); 2.4102 (12.19); 1.4076 (16.00); -0.0002 (6.46)

[DMSO], Spektrometer: 399.95MHz 8.1233 (2.80); 8.1093 (5.37); 8.0954 (2.82); 7.4992 (15.95); 7.4942 (16.00); 7.4398 (6.98); 7.4358 (5.14); 7.4218 (9.64); 7.4169 (8.86); 7.4014 (0.41); 7.3420 (4.40); 7.3362 (5.93); 7.3234 (7.10); 7.3185 (10.40); 7.3021 (3.55); 7.2978 (4.59); 7.2840 (10.82); 7.2796 (9.52); 7.2710 (9.52); 7.2667 (9.41); 7.2646 (9.80); 7.2613 (6.16); 7.2524 (8.16); 7.2470 (6.78); 7.2341 (2.70); 7.2289 (2.08); 6.7953 (15.49); 6.7903 (15.18); 3.4475 (5.04); 3.4316 (9.29); 3.4153 (8.52); 3.41 12 (9.56); 3.3963 (5.85); 3.3621 (0.58); 3.3349 (206.81); 3.31 15 (0.51); 2.9492 (10.46); 2.9299 (14.13); 2.9123 (9.09); 2.8907 (0.91); 2.7320 (0.68); 2.7122 (1.23); 2.6765 (0.54); 2.6720 (0.67); 2.6674 (0.56); 2.6431 (0.59); 2.5826 (0.32); 2.5686 (0.69); 2.5615 (1.13); 2.5422 (270.64); 2.5254 (1.92); 2.5205 (2.33); 2.51 19 (34.55); 2.5074 (69.97); 2.5028 (92.97); 2.4983 (68.09); 2.4937 (32.87); 2.4833 (84.56); 2.3685 (1.18); 2.3341 (0.45); 2.3297 (0.62); 2.3250 (0.47); 2.3201

14-13 2-chlor-phenyl CH2 CH2 H (0.66); 0.0079 (1.68); -0.0002 (51.87); -0.0086 (1.55)

[DMSO], Spektrometer: 399.95MHz 8.0559 (0.60); 8.0420 (1.15); 8.0280 (0.59); 7.5514 (2.92); 7.5309 (3.33); 7.5078 (2.86); 7.5002 (3.65); 7.4947 (3.01); 7.2304 (1.61); 7.2254 (1.54); 7.2098 (1.42); 7.2048 (1.36); 6.7694 (2.98); 6.7644 (2.87); 3.4345 (1.03); 3.4173 (2.30); 3.4022 (2.35); 3.3849 (1.27); 3.3401 (146.07); 2.8254 (1.83); 2.8077 (3.43); 2.7900 (1.63); 2.7122 (0.37); 2.5422 (79.74); 2.5249 (0.91); 2.51 17 (16.17); 2.5074 (31.1 1); 2.5029 (40.60); 2.4983 (29.98); 2.4940 (14.65); 2.4679 (16.00); 2.3684 (0.36); 0.0075 (0.46); -0.0002 (10.57); -0.0085

14-14 3 ,4-dichlor-phenyl CH2 CH2 H (0.34)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 |ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz 8.0618 (0.56); 8.0480 (1.09); 8.0340 (0.56); 7.5030 (3.07); 7.4980 (3.08); 7.4391 (1.36); 7.4343 (2.72); 7.4296 (1.54); 7.3030 (6.08); 7.2982 (5.74); 6.7674 (2.96); 6.7624 (2.93); 3.4453 (0.91); 3.4280 (2.18); 3.4132 (2.21 ); 3.3959 (1.00); 3.3367 (59.76); 2.8379 (1.72); 2.8204 (3.32); 2.8028 (1.53); 2.5426 (53.55); 2.5257 (0.33); 2.5207 (0.55); 2.5122 (7.18); 2.5077 (14.57); 2.5031 (19.50); 2.4986 (14.37); 2.4941 (6.93); 2.4668

14-15 3,5- dichlor-pheny 1 CH2 CH2 H (16.00); -0.0002 (5.83)

14-16 3-chlor-phenyl CH2 CH2 - H US 20090163545

14-17 2-fluor-phenyl CH2 CH2 - H CAS: 1088190-17-3

14-18 2,6-difluor-phenyl CH2 CH2 - H CAS: 1 197478-54-8

[DMSO], Spektrometer: 399.95MHz 8.1857 (0.57); 8.1712 (1.12); 8.1569 (0.57); 7.4946 (2.99); 7.4896 (2.98); 7.4627 (4.66); 7.4426 (6.42); 7.3002 (2.26); 7.281 1 (2.21); 7.2792 (2.1 1); 7.2600 (1.48); 6.7910 (2.95); 6.7860 (2.87); 3.4301 (0.86); 3.4139 (1.91 ); 3.4087 (1.15); 3.3981 (1.69); 3.3937 (1.91); 3.3790 (1.12); 3.3405 (76.83); 3.1400 (1.96); 3.1205 (2.67); 3.1035 (1.53); 2.5429 (51.41); 2.5260 (0.42); 2.5126 (8.08); 2.5081 (16.01); 2.5035 (21.17); 2.4989 (15.52);

14-19 2,6-dichlor-phenyl CH2 CH2 H 2.4945 (7.45); 2.4795 (16.00); -0.0002 (6.48)

[DMSO], Spektrometer: 399.95MHz 8.0845 (0.58); 8.0705 (1.06); 8.0569 (0.55); 7.5785 (2.44); 7.5747 (2.43); 7.5658 (1.02); 7.5575 (1.52); 7.5419 (5.32); 7.5245 (0.81); 7.4993 (3.09); 7.4943 (3.1 1); 6.7706 (2.96); 6.7656 (2.89); 3.4655 (1.01); 3.4483 (2.10): 3.4335 (2.10); 3.4154 (1.1 1); 3.3419 (67.23); 2.9274 (1.86); 2.9094 (3.22); 2.8916 (1.83); 2.5431 (55.77); 2.5214 (0.51);

3 -(trifluormethyl)- 2.5129 (6.99); 2.5085 (14.07); 2.5039 (18.66): 2.4993 (13.63); 2.4948 (6.53); 2.4751

14-20 phenyl CH2 CH2 H (0.81): 2.4642 (16.00); -0.0002 (6.39)

4-(trifluormethyl)-

CAS: 1007769-64-3

14-21 phenyl CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz 8.1484 (0.61); 8.1343 (1.17); 8.1203 (0.61 ); 7.5084 (3.47); 7.5034 (3.53); 7.1648 (0.76); 7.1578 (0.98); 7.1502 (1.82); 7.1427 (2.14); 7.1340 (3.07); 7.1258 (1.29); 7.1216 (3.55); 7.1 181 (3.61); 7.1081 (2.67); 7.1027 (1.42); 7.0965 (1.18); 6.8060 (3.37); 6.8010 (3.34); 3.3644 (1.45); 3.3411 (76.78); 3.3255 (2.67); 3.31 10 (1.35); 2.8058 (2.23); 2.791 1 (1.71 ); 2.7859 (2.39); 2.7669 (1.98); 2.5421 (59.24); 2.5254 (0.42); 2.5205 (0.61); 2.51 17 (7.72); 2.5072 (15.80); 2.5026 (21.96); 2.4983 (30.70); 2.4938 (8.81); 2.3199

14-22 2-methyl-phenyl CH2 CH2 H (16.00); -0.0002 (7.31)

[DMSO], Spektrometer: 399.95MHz 8.2303 (0.41); 8.2158 (0.83); 8.2012 (0.42); 7.5185 (2.11); 7.5135 (2.15); 6.8170 (2.10); 6.81 17 (2.37); 6.8043 (4.37); 3.3396 (48.79): 3.2143 (0.52); 3.1998 (0.92); 3.1950 (0.75); 3.1860 (0.89); 3.1791 (0.74); 3.1726 (0.96); 3.1586 (0.63); 2.7717 (1.12); 2.7584 (0.85); 2.7507 (1.10); 2.7452 (0.89); 2.7308 (1.02); 2.5420 (33.55); 2.5145 (1 1.87);

2,4,6-trimethyl- 2.5071 (9.55); 2.5025 (12.60); 2.4980 (9.40); 2.4935 (4.67); 2.2973 (16.00); 2.1809

14-23 phenyl CH2 CH2 H (7.31 ); -0.0002 (4.69)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Chemische Berichte (1986), 119(8), 2553-65

[DMSO], Spektrometer: 399.95MHz 8.0475 (0.51); 8.0337 (1.01); 8.0198 (0.51); 7.5024 (2.60); 7.4974 (2.65); 6.8695 (2.09); 6.8491 (2.78); 6.8088 (4.43); 6.8040 (4.50); 6.7378 (1.38); 6.7330 (1.25); 6.7175 (1.04); 6.7127 (0.95); 3.7181 (15.83); 3.7091 (16.00); 3.3989 (0.79); 3.3829 (1.50); 3.3659 (1.55); 3.3624 (1.74); 3.3388 (1 15.29); 2.7441 (1.42); 2.7247 (2.02); 2.7069 (1.30);

3,4-bismethoxy- 2.5418 (69.00); 2.5249 (0.58); 2.5201 (0.80); 2.51 15 (10.33); 2.5070 (21.00); 2.5024

14-24 phenyl CH2 CH2 H (28.16); 2.4978 (20.98); 2.4934 (10.56); 2.4851 (14.30); -0.0002 (7.72)

14-25 phenyl CH2 CH2 - H CAS: 541523-79-9

C(CH2-

14-26 4-chlor-phenyl CH2) CH2 H

C(CH2-

14-27 2,4-dichlor-phenyl CH2) CH2 H

C(CH2-

14-28 4-chlor-phenyl CH2 CH2) H

C(CH2-

14-29 2,4-dichlor-phenyl CH2 CH2) H

14-30 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 14-31, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1991 (2,44); 8,1856 (4,74); 8,1721 (2,51); 7,5692 (10,73); 7,5627 (1 1,64); 7,5192

(1 1 ,22); 7,5142 (1 1 ,71); 7,3808 (5,45); 7,3743 (5,19); 7,3586 (7,5); 7,3522 (7,37);

7,2458 (12,65); 7,2235 (9,28); 6,8287 (1 1,22); 6,8238 (1 1,45); 4,1873 (7,13); 4,1722

(16); 4, 1572 (7,9); 3,589 (3,92); 3,5743 (10,95); 3,5599 (10,65); 3,545 (3,62); 3,3329

(48,62); 2,6604 (0,37); 2,544 (41 ,84); 2,509 (30,08); 2,5003 (78,98); 2,3368 (0,51); -

14-31 2,4-dichlor-phenyl 0 CH2 CH2 H 0,0002 (1 ,63)

14-32 4-chlor-phenyl CH2 CH2 CH2 H

14-33 4-chlor-phenyl NCH3 CH2 CH2 H

14-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

14-35 4-chlor-phenyl CH(OCH3) CH2 - H

14-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

CAS: 1036192-62-7; Verbindung Nr. 14-37, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1549 (2,8); 8, 141 1 (5,13); 8,1277 (2,85); 7,5103 (13,94); 7,5053 (14,05); 7,3436 (8,86); 7,3407 (8,33); 7,3308 (9,73); 7,3279 (8,6); 6,9666 (7, 13); 6,9581 (9,85); 6,9539 (7,12); 6,9454 (8,99); 6,9046 (9,56); 6,9026 (9,21); 6,8962 (7,64); 6,8081 (14, 18); 6,8032 (13,97); 3,4417 (4,84); 3,424 (10,35); 3,4092 (10,55); 3,3909 (5,74); 3,3313

14-37 2-thienyl CH2 CH2 H (1 14,75); 3,0349 (9,53); 3,0166 (16); 2,9985 (8,1 1); 2,6758 (0,39); 2,6712 (0,5); 2,6668

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(0,37); 2,6529 (0,45); 2,5414 (26,01); 2,5243 (1 ,99); 2,5066 (56,04); 2,5021 (73,51); 2,4974 (60,73); 2,4927 (97,05); 2,3293 (0,87); -0,0002 (1 ,26)

14-38 3-thienyl CH2 CH2 - H

14-39 2-furyl CH2 CH2 - H DE 2006471

14-40 3-furyl CH2 CH2 - H

14-41 phenyl CH2 CH2 CH(CH3) H US 20090163545

14-42 phenyl CH2 CH2 CH2 H

14-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

14-44 4-t-butyl-phenyl CH2 CH2 CH2 H

14-45 4-methyl-phenyl CH2 CH2 CH2 H

14-46 phenyl CH2 CH2 CH(CH2CH3) H

14-47 2-methoxy-phenyl CH2 CH2 CH2 H

14-48 2-methyl-phenyl CH2 CH2 CH2 H

14-49 3 -methyl-phenyl CH2 CH2 CH2 H

14-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 14-51, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0323 (3,22); 8,0184 (6,02); 8,0048 (3,33); 7,5324 (0,4); 7,5275 (0,41); 7,5013 (15,34); 7,4964 (15,51); 7,3451 (1 ,63); 7,328 (3,84); 7,3246 (3,58); 7,3073 (7,14); 7,2866 (4,63); 7,2696 (2,07); 7,1377 (0,34); 7,1 164 (0,46); 7,1001 (1); 7,0958 (1,45); 7,083 (10); 7,0631 (16); 7,0433 (8,28); 7,0297 (1 ,15); 6,8867 (0,35); 6,8816 (0,35); 6,7981 (15,55); 6,7933 (15,34); 6,5018 (0,35); 6,496 (0,68); 3,3608 (0,43); 3,3327 (1 13,68); 3,2342 (4,87); 3,2176 (9,88); 3,2 (9,94); 3, 1832 (5,13); 2,6715 (7,4); 2,6523 (1 1,98); 2,633 (7,7); 2,5434 (15,29); 2,5084 (61 ,17); 2,504 (80,08); 2,4996 (60,68); 2,4836 (81, 14); 2,3353 (0,43); 2,3308 (0,56); 2,3263 (0,45); 2,3203 (0,69); 1,7725 (2,67); 1 ,7532 (6,95);

14-51 2,6-difluor-phenyl CH2 CH2 CH2 H 1 ,7348 (10,07); 1,7159 (6,46); 1 ,6973 (2,32); -0,0002 (1 ,34)

14-52 4-chlor-phenyl CH2 CH2 CH2 H

14-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

14-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

14-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

14-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

14-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

14-58 3 -trifluormethyl- CH2 CH2 CH(CH3) H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr. phenyl

14-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

14-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

14-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

14-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

14-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

4-trifluormethyl-

14-64 phenyl CH2 CH2 CH(CH3) H

14-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

14-66 4-phenoxy-phenyl CH2 CH2 CH2 H

14-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

14-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

14-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

2-difluormethoxy-

14-70 phenyl CH2 CH2 CH(CH3) H

14-71 4-methoxy-phenyl CH2 CH2 CH2 H

14-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

14-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

14-74 4-fluor-phenyl CH2 CH2 CH2 H

14-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

14-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

14-77 2-chlor-phenyl CH2 CH2 CH2 H

14-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl WO-A 2007/060164

Verbindung Nr. 14-79, Solvent: [DMSO], Spektrometer: 399.95MHz 8,0171 (3); 8,0039 (5,46); 7,9908 (3, 16); 7,506 (13,76); 7,5012 (14,16); 7,3189 (8,22); 7,3166 (7,79); 7,3061 (9,13); 7,3039 (8,3); 6,9506 (6,59); 6,942 (9,3); 6,9381 (7,06); 6,9294 (8,33); 6,8849 (9,82); 6,8769 (8,12); 6,8296 (14,52); 6,8249 (14,59); 6,6403 (0,36); 3,3277 (177,24); 3,2788 (0,32); 3,2567 (5,21 ); 3,2399 (1 1 ,67); 3,2241 (1 1 ,82); 3,2072 (5,66); 2,8452 (9,12); 2,826 (16); 2,807 (10); 2,6709 (1 , 15); 2,6668 (0,92); 2,652 (0,52); 2,5412 (3,07); 2,5061 (125,99);

14-79 2-thienyl CH2 CH2 CH2 H 2,5019 (163,82); 2,4976 (130,24); 2,4925 (132,62); 2,3287 (1 ,52); 1 ,8629

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(2,88); 1,8444 (8,58); 1,826 (11,62); 1,8078 (8,24); 1,7893 (2,67); -0,0002 (2,3)

Verbindung Nr.14-80, Solvent: [DMSO], Spektrometer: 601.6MHz

19,9748 (0,32); 8,5435 (1,84); 8,1811 (0,53); 8,1329 (0,44); 7,8134 (0,37); 7,7811 (4,16); 7,5088 (0,96); 7,5054 (0,98); 7,3929 (1,4); 7,3903 (2,11); 7,3877

(1.36) ; 7,384 (11 ,28); 7,3814 (11 ,53); 7,3748 (1 ,67); 7,3703 (2,55); 7,3677 (2,64); 7,3667 (2,58); 7,364 (2,54); 7,3609 (1,36); 7,3583 (2,12); 7,3558 (2,06); 7,3193 (0,54); 7,3105 (0,53); 6,9507 (0,46); 6,9167 (5,02); 6,9051 (1,66); 6,9026 (1,67); 6,8973 (1,83); 6,8736 (0,7); 6,8356 (1,19); 6,796 (0,99); 6,7927 (0,99); 6,7442 (0,39); 6,6313 (0,73); 6,6251 (0,37); 6,613 (0,37); 6,579 (0,7); 6,5069 (6,56); 6,4758 (0,74); 6,3956 (1,37); 6,1166 (0,43); 6,1073 (0,37); 5,5824 (0,84); 5,5744 (0,66); 5,5696 (0,76); 4,9338 (0,37); 4,9239 (0,32); 4,2175 (0,37); 4,1973 (0,42); 4,0375 (0,39); 4,0275 (0,64); 4,0176 (0,38); 3,8042 (0,34); 3,7954 (0,33); 3,5638 (0,39); 3,5318 (1,53); 3,5278 (1,53); 3,4296 (2,98); 3,4196 (3,25); 3,408 (2,33); 3,3962 (1,41); 3,3669 (1,94); 3,3556

(3.37) ; 3,3263 (1521,55); 3,2793 (2,17); 3,2689 (1,59); 3,0844 (0,99); 3,0567 (1,21); 2,994 (11,61); 2,9893 (3,86); 2,9778 (6,69); 2,9662 (3,74); 2,9464 (1,64); 2,9344 (2,05); 2,9225 (1,74); 2,9166 (1,49); 2,9053 (1,88); 2,8939 (1,1); 2,7631 (0,45); 2,7448 (0,79); 2,7173 (0,63); 2,653 (5,71); 2,6191 (1,65); 2,6161 (3,65); 2,613 (5,07); 2,61 (3,6); 2,607 (1,53); 2,5702 (0,39); 2,5407 (1859,34); 2,5224 (10,56); 2,5193 (13,3); 2,5161 (13,34); 2,5074 (276,9); 2,5044 (589,98); 2,5013 (809,48); 2,4982 (584,41); 2,4952 (269,68); 2,4862 (9,63); 2,4736 (2,03); 2,4364 (2,02); 2,4307 (1,21); 2,4243 (6,23); 2,3916 (1,99); 2,3885 (3,93); 2,3855 (5,36); 2,3824 (3,92); 2,3794 (1,93); 2,3288 (0,8); 2,2921 (2,69); 2,2896 (2,66); 2,2853 (3,73); 2,2813 (1,91); 2,2411 (0,63); 2,2013 (5,61); 2,1787 (0,59); 2,1379 (5,98); 2,1297 (1,58); 2,1266 (1,16); 2,1124 (2,08); 2,1077 (2,88); 2,0771 (2,41); 2,0734 (6,05); 2,0541 (1,21); 2,0419 (0,92); 1,9378(0,35); 1,9084 (6,54); 1,6954 (16); 1,5254 (0,34); 1,4886 (0,32); 1,2978 (0,33); 1,2762 (0,52); 1,2583 (0,48); 1,2352 (0,88); 1,1862 (0,34); 1,1742 (0,63); 0,0052 (1 ,63);

14-80 4-chlor-2-thienyl CH2 CH2 H -0,0002 (52,42); -0,0058 (1,46)

Tabelle 15

Verbindungen der Formel 1-15

1-15

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

15-1 3 -methyl-2-thienyl CH2 CH2 - H

15-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

15-3 4-chlor-phenyl CH2 CH2 - H

15-4 2,4-dichlor-phenyl CH2 CH2 - H

15-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

15-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

15-7 4-chlor-phenyl CH(CH3) CH2 - H

15-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

15-9 4-chlor-phenyl CH2 CH(CH3) - H

15-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

15-11 4-chlor-phenyl C(CH3)2 CH2 - H

15-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H

15-13 2-chlor-phenyl CH2 CH2 - H

15-14 3 ,4-dichlor-phenyl CH2 CH2 - H

15-15 3,5- dichlor-pheny 1 CH2 CH2 - H

15-16 3-chlor-phenyl CH2 CH2 - H

15-17 2-fluor-phenyl CH2 CH2 - H

15-18 2,6-difluor-phenyl CH2 CH2 - H

15-19 2,6-dichlor-phenyl CH2 CH2 - H

15-20 3 -(trifluormethyl)-phenyl CH2 CH2 - H

15-21 4-(trifluormethyl)-phenyl CH2 CH2 - H

15-22 2-methyl-phenyl CH2 CH2 - H

15-23 2,4,6-trimethyl-phenyl CH2 CH2 - H

15-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H

15-25 phenyl CH2 CH2 - H

15-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

15-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

15-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

72 -

73-

Tabelle 16

Verbindungen der Formel 1-16

1-16

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

16-1 3 -methyl-2-thienyl CH2 CH2 - H

Verbindung Nr.16-2, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2265 (2,17); 8,2125 (4,09); 8,1989 (2,11); 7,8375 (15,8); 7,8321 (15,85); 7,5699 (11,89); 7,5647 (12,21); 7,4271 (6,55); 7,4064 (15,53); 7,3811 (10,54); 7,3758 (9,69); 7,3604 (4,25); 7,3552 (4,28); 6,9445 (16); 6,939 (15,83); 3,4406 (0,35); 3,4211 (0,46); 3,3392 (914,76); 3,2877 (0,65); 3,2526 (3,7); 3,2354 (8,13); 3,2202 (8,13); 3,203 (3,76); 2,7346 (6,71); 2,7157 (8,75); 2,7129 (8,89); 2,6961 (7,22); 2,681 (0,86); 2,6764 (1,5); 2,6718 (1,99); 2,6673 (1,49); 2,6628 (0,72); 2,5811 (0,48); 2,5422 (547,01); 2,5293 (3,15); 2,5251 (6,34); 2,5204 (9,64); 2,5118 (108,4); 2,5073 (217,84); 2,5028 (285,86); 2,4982 (204,88); 2,4937 (97,11); 2,3681 (2,18); 2,3386 (0,65); 2,3341 (1,35); 2,3295 (1,84); 2,3249 (1,33); 2,3204 (0,61); 2,0747 (1,58); 1,8031 (1,88); 1,7845 (5,01); 1,766 (6,67); 1,7475 (4,69); 1 ,7293 (1 ,67); 1 ,2346 (0,46); 0,008 (0,78); -

16-2 2,4-dichlor-phenyl CH2 CH2 CH2 H 0,0001 (23,32); -0,0085 (0,68)

Verbindung Nr.16-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2445 (1,5); 8,2305 (2,78); 8,2166 (1,44); 7,8308 (11,39); 7,8254 (11,53); 7,3664 (1,16); 7,36 (9,59); 7,3552 (3,61); 7,3441 (4,26); 7,339 (16); 7,3329 (2,13); 7,2736 (2,05); 7,2675 (13,43); 7,2627 (4,11); 7,2512 (3,09); 7,2464 (8,65); 6,9182 (11,22); 6,9128 (11,15); 3,4262 (2,78); 3,409 (5,42); 3,3941 (5,2); 3,3909 (5,28); 3,3755 (3,76); 3,3336 (547,71); 2,8154 (4,98); 2,7968 (8); 2,7789 (4,42); 2,7111 (1 ,67); 2,6802 (0,49); 2,6757 (0,95); 2,6712 (1,32); 2,6666 (0,98); 2,662 (0,49); 2,5802 (0,55); 2,5417 (454,3); 2,5289 (2,7); 2,5282 (2,7); 2,5245 (4,72); 2,5196 (7,15); 2,5111 (73,39); 2,5067 (147,53); 2,5021 (195,1); 2,4975 (141,15); 2,493 (67,83); 2,3673 (1,67); 2,338 (0,45); 2,3334 (0,91 ); 2,3289 (1 ,27); 2,3243 (0,91 ); 2,3201

16-3 4-chlor-phenyl CH2 CH2 H (0,44); 2,0745 (1,08); 0,008 (0,66); -0,0002 (19,22); -

75 -

Physikalische Daten: H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

0,0085 (0,58)

Verbindung Nr. 16-4, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2802 (2); 8,2663 (3,79); 8,2522 (1 ,9); 7,8388 (0,4); 7,8288 (14,34); 7,8234 (14,38); 7,5893 (9,07); 7,5847 (9,59); 7,3901 (2,34); 7,3854 (1 ,75); 7,3695 (12,09); 7,3648 (13,18); 7,3598 (16); 7,3392 (2,51 ); 6,9057 (14,27); 6,9003 (14,09); 3,4512 (3,36); 3,4343 (7,51 ); 3,419 (7,4); 3,4013 (4,01 ); 3,3374 (813,42); 3,2929 (0,6); 3,2715 (0,33); 2,9366 (6,6); 2,9186 (1 1 ,55); 2,901 1 (5,75); 2,71 19 (1 ,92); 2,6809 (0,59); 2,6763 (1 ,24); 2,6717 (1 ,69); 2,6671 (1 ,25); 2,6626 (0,62); 2,5893 (0,36); 2,582 (0,54); 2,542 (502,66); 2,5299 (2,9); 2,5249 (5,94); 2,5202 (8,82); 2,51 17 (97,53); 2,5072 (196,78); 2,5026 (259,04); 2,4981 (187,41 ); 2,4936 (89,92); 2,4638 (0,46); 2,3682 (1 ,95); 2,3386 (0,59); 2,3339 (1 ,22); 2,3293 (1 ,68); 2,3248 (1 ,23); 2,3204 (0,6); 2,0746 (1 ,3); 1 ,2349 (0,36); 0,008 (0,76);

16-4 2,4-dichlor-phenyl CH2 CH2 H -0,0002 (21 ,93); -0,0084 (0,65)

16-5 4-chlor-phenyl CH(OCH3) CH(CH3) H

16-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) H

Verbindung Nr. 16-7, Solvent: [DMSO], Spektrometer: 399.95MHz->8,1781 (1 ,32); 8,1638 (2,52); 8,1494 (1 ,27); 7,8147 (9,09); 7,8093 (9,1 ); 7,3697 (0,89); 7,3635 (7,76); 7,3588 (2,77); 7,3473 (3,5); 7,3423 (13,71 ); 7,3365 (1 ,78); 7,2919 (1 ,86); 7,2859 (12,6); 7,281 1 (3,49); 7,2695 (2,57); 7,2647 (7,32); 6,8862

(9.03) ; 6,8808 (8,86); 3,3949 (0,38); 3,3769 (1 , 15); 3,3582 (2,62); 3,3334 (397,26); 3,3101 (4,09); 3,3041 (3,14); 3,2893 (2,84); 3,2748 (0,77); 3,2707 (0,79); 3,2565 (0,68); 3,0434 (1 ,3); 3,0255 (2,56); 3,0077 (2,48); 2,9899 (1 ,14); 2,71 18 (1 ,38); 2,6801 (0,42); 2,6758 (0,84); 2,6713 (1 , 1 1 ); 2,6669 (0,83); 2,6624 (0,41 ); 2,5864 (0,33); 2,5849 (0,34); 2,5791 (0,49); 2,5769 (0,53); 2,5761 (0,54); 2,5754 (0,55); 2,5746 (0,57); 2,5725 (0,63); 2,5681 (0,89); 2,5674 (0,89); 2,5614 (1 ,41 ); 2,5607 (1 ,46); 2,5415 (319,87); 2,5245 (3,88); 2,5197 (5,75); 2,51 13 (63,24); 2,5068 (126,65); 2,5023 (165,95); 2,4978 (120,23); 2,4934 (58,27); 2,368 (1 ,33); 2,3382 (0,37); 2,3336 (0,76); 2,329

(1 .04) ; 2,3246 (0,77); 2,0744 (0,88); 1 ,2344 (0,37); 1 ,21 14 (16); 1 ,1939 (15,75); 0,0079 (0,54); -0,0002

16-7 4-chlor-phenyl CH(CH3) CH2 H (15,37); -0,0086 (0,46)

16-8 2,4-dichlor-phenyl CH(CH3) CH2 H Verbindung Nr. 16-8, Solvent: [DMSO], Spektrometer:

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

(4,69); 2,8723 (4,08); 2,8584 (0,75); 2,8383 (0,84); 2,6757 (0,72); 2,671 1 (0,98); 2,6666 (0,72); 2,6623 (0,36); 2,5413 (60,01 ); 2,5243 (3,82); 2,51 1 (58,91 ); 2,5066 (1 16,35); 2,5021 (151 ,66); 2,4976 (109,48); 2,4931 (52,84); 2,3333 (0,71 ); 2,3288 (0,98); 2,3244 (0,72); 2,0747 (0,65); 1 ,1716 (16); 1 ,1549 (15,77); 0,0077 (0,49); -0,0002 (13,39); -0,0085 (0,43)

Verbindung Nr. 16-1 1 , Solvent: [DMSO],

Spektrometer: 399.95MHz

7,9042 (0,4); 7,8888 (0,76); 7,8729 (0,39); 7,8129 (2,22); 7,8077 (2,27); 7,4348 (2,04); 7,43 (0,84); 7,4183 (1 ,03); 7,4132 (3,92); 7,4071 (0,65); 7,371 1 (0,57); 7,365 (3,9); 7,3601 (1 ,14); 7,3479 (0,76); 7,3433 (2,1 ); 6,8863 (2,28); 6,881 (2,3); 3,387 (2,85); 3,371 1 (2,97); 3,3318 (1 18,82); 2,71 1 (0,37); 2,6709 (0,34); 2,5416 (81 ,35); 2,5063 (40,7); 2,5019 (53,44); 2,4975 (40,15); 2,3674 (0,36); 2,3286 (0,34); 1 ,2761

16-11 4-chlor-phenyl C(CH3)2 CH2 H (16); -0,0002 (4,07)

Verbindung Nr. 16-12, Solvent: [DMSO],

Spektrometer: 399.95MHz

7,9051 (0,38); 7,8905 (0,75); 7,8747 (0,39); 7,7997 (3,06); 7,7943 (3,06); 7,5331 (2,55); 7,5273 (2,7); 7,4702 (1 ,5); 7,4486 (2,27); 7,3703 (1 ,57); 7,3645 (1 ,48); 7,3487 (1 ,08); 7,3429 (1 ,01 ); 6,8516 (3,1 ); 6,8462 (3,12); 3,7316 (2,67); 3,7156 (2,64); 3,3338 (84,14); 2,71 18 (0,34); 2,6715 (0,36); 2,5417 (92,01 ); 2,5248 (1 ,39); 2,5199 (2,2); 2,51 15 (21 ,3); 2,507 (42,52); 2,5024 (55,96); 2,4978 (40,68); 2,4933 (20,13); 2,3681 (0,35); 2,3291 (0,34); 1 ,4263 (16); -

16-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 0,0002 (5,88)

Verbindung Nr. 16-13, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,3065 (2,1 ); 8,2927 (3,89); 8,2788 (1 ,98); 7,8308 (15,98); 7,8254 (15,89); 7,4416 (5,44); 7,4377 (4, 19); 7,4234 (7,48); 7,4186 (6,89); 7,3522 (3,47); 7,3467 (4,52); 7,3337 (5,46); 7,3288 (7,43); 7,3136 (0,47); 7,3079 (2,51 ); 7,3036 (3,37); 7,2896 (7,74); 7,2854 (7,06); 7,2752 (7,12); 7,2725 (6,97); 7,2689 (7,49); 7,2566 (5,91 ); 7,2512 (5,15); 7,2382 (1 ,9); 7,2331 (1 ,5); 6,9286 (16); 6,9231 (15,76); 3,4579 (3,9); 3,4414 (7,26); 3,4258 (6,72); 3,422 (7,37); 3,407 (4,47); 3,3326 (766); 3,2906 (0,46); 3,2753 (0,32); 2,9553 (7,61 ); 2,9362 (10,86); 2,9187 (6,6); 2,71 13 (2,34); 2,6802 (0,7); 2,6758 (1 ,46); 2,6712 (1 ,97); 2,6666 (1 ,47); 2,6624 (0,73); 2,5788 (0,68); 2,5416 (618,96);

16-13 2-chlor-phenyl CH2 CH2 H 2,5306 (3,62); 2,5298 (3,38); 2,529 (3,28); 2,5283

79 -

Physikalische Daten: H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(0,38); 2,6759 (0,71 ); 2,6714 (0,97); 2,6669 (0,73); 2,5419 (278,3); 2,5245 (3,3); 2,51 12 (55,54); 2,5069 (1 10,59); 2,5024 (145,42); 2,4979 (106,86); 2,4936 (53,13); 2,3678 (1 ,26); 2,3335 (0,68); 2,329 (0,95); 2,3246 (0,69); 2,0746 (0,65); 0,0075 (0,42); -0,0002 (1 1 ,29); -0,0083 (0,44)

Verbindung Nr. 16-16, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,2557 (2,19); 8,2423 (4); 8,2286 (2,14); 7,833 (14,67); 7,8277 (14,59); 7,3599 (0,54); 7,3555 (0,34); 7,3457 (3,92); 7,3391 (1 ,01 ); 7,3262 (9,92); 7,3122 (10,65); 7,3075 (16); 7,2806 (5, 14); 7,2774 (7,06); 7,2608 (3,08); 7,256 (3, 1 1 ); 7,2528 (2,17); 7,2471 (0,47); 7,2082 (7,06); 7,1894 (4,71 ); 6,9162 (15,14); 6,9108 (14,74); 3,4452 (4,25); 3,428 (8,3); 3,4131 (8,13); 3,4105 (7,99); 3,3947 (5,3); 3,3375 (787,6); 2,8358 (7,39); 2,8174 (12,52); 2,7996 (6,82); 2,7795 (0,34); 2,71 18 (2,43); 2,6761 (1 ,3); 2,6716 (1 ,73); 2,6671 (1 ,26); 2,6626 (0,66); 2,6003 (0,34); 2,5848 (0,53); 2,542 (551 ,34); 2,5249 (5,65); 2,51 14 (95,76); 2,507 (191 ,1 1 ); 2,5025 (250,48); 2,4979 (180,46); 2,4935 (86,74); 2,3679 (2,36); 2,3383 (0,55); 2,3338 (1 ,15); 2,3292 (1 ,58); 2,3247 (1 , 14); 2,3204 (0,55); 2,0745 (1 ,21 ); 1 ,2347 (0,4); 0,008 (0,71 ); -0,0002 (20,67); -

16-16 3-chlor-phenyl CH2 CH2 H 0,0084 (0,64)

Verbindung Nr. 16-17, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,306 (2,32); 8,2924 (4,24); 8,2782 (2,22); 7,8298 (15,72); 7,8244 (15,8); 7,3263 (2,46); 7,3223 (3,02); 7,3077 (4,79); 7,3032 (6,55); 7,2952 (1 ,92); 7,2838 (5,05); 7,2821 (5,06); 7,2665 (3,48); 7,261 (4,46); 7,2564 (2,34); 7,2472 (2,5); 7,2428 (1 ,94); 7,1762 (4,74); 7,1539 (10,18); 7,1376 (8,3); 7,1347 (8,56); 7, 1 192 (3,39); 7,1 163 (3); 6,9189 (16); 6,9134 (15,89); 3,4362 (4,39); 3,4196 (8,34); 3,4036 (7,86); 3,4001 (8,67); 3,3849 (5,64); 3,3373 (773,29); 2,8615 (6,75); 2,8429 (10,92); 2,8247 (5,95); 2,71 16 (2,39); 2,6762 (1 ,26); 2,6715 (1 ,65); 2,667 (1 ,24); 2,5419 (574,76); 2,5248 (5,27); 2,5199 (7,82); 2,51 13 (90,74); 2,507 (184,1 ); 2,5025 (243,84); 2,4979 (179,18); 2,4935 (88,33); 2,3678 (2,34); 2,3337 (1 ,13); 2,3292 (1 ,56); 2,3246 (1 ,15); 2,3204 (0,57); 2,0744 (1 ,21 ); 1 ,2343

16-17 2-fluor-phenyl CH2 CH2 H (0,39); 0,0079 (0,69); -0,0002 (20,48); -0,0085 (0,7)

Verbindung Nr. 16-18, Solvent: [DMSO],

Spektrometer: 399.95MHz

16-18 2,6-difluor-phenyl CH2 CH2 H 8,364 (2,34); 8,3494 (4,36); 8,3348 (2,24); 7,8359

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

(31 ,51 ); 2,4932 (15,43); 2,3677 (0,34); 2,2961 (16); 2,1819 (6,95); -0,0002 (3,57)

Verbindung Nr. 16-24, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,2226 (0,5); 8,208 (0,98); 8,1943 (0,5); 7,8349 (3,23); 7,8295 (3,28); 6,9434 (3,24); 6,9379 (3,24); 6,8729 (2,06); 6,8526 (2,75); 6,8156 (2, 19); 6,8108 (2,47); 6,7444 (1 ,39); 6,7396 (1 ,28); 6,7241 (1 ,02); 6,7193 (0,96); 3,7235 (15,97); 3,7103 (16); 3,41 17 (0,84); 3,3953 (1 ,51 ); 3,3755 (1 ,58); 3,3602 (1 ,47); 3,3354 (157,64); 3,3019 (0,33); 2,7517 (1 ,47); 2,7323 (2, 14); 2,7144 (1 ,36); 2,6712 (0,36); 2,5416 (70,4); 2,531 1 (0,37); 2,5244 (1 ,1 1 ); 2,51 1 1 (20,3); 2,5067 (41 ,01 ); 2,5022 (54,16); 2,4976 (39,63); 2,4931 (19,3); 2,3289

16-24 3 ,4-bismethoxy-phenyl CH2 CH2 H (0,33); -0,0002 (4,43)

Verbindung Nr. 16-25, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,2663 (2,05); 8,2526 (3,66); 8,2388 (1 ,93); 7,833 (15,73); 7,8276 (15,67); 7,3201 (4,91 ); 7,3164 (2, 18); 7,3018 (12,21 ); 7,2882 (4,01 ); 7,2836 (12,13); 7,2459 (10,31 ); 7,2424 (15,72); 7,2254 (1 1 ,54); 7,2099 (2,67); 7,2049 (6,44); 7,1994 (1 ,55); 7, 1906 (1 ,47); 7,187 (2,23); 7,1837 (1 , 12); 6,947 (0,45); 6,9356 (16); 6,9301 (15,52); 3,4556 (0,39); 3,433 (4,52); 3,4174 (7,23); 3,4149 (6,85); 3,41 1 1 (5,07); 3,4003 (6,85); 3,396 (8); 3,381 1 (6,01 ); 3,3378 (832); 3,2781 (0,38); 2,8224 (7,58); 2,8027 (10,02); 2,7847 (6,73); 2,71 17 (2,35); 2,6804 (0,66); 2,676 (1 ,26); 2,6714 (1 ,72); 2,6668 (1 ,27); 2,6623 (0,66); 2,5417 (586,69); 2,5248 (5,85); 2,5199 (8,66); 2,51 14 (97,09); 2,5069 (195,08); 2,5023 (255,88); 2,4978 (184,52); 2,4933 (88,29); 2,3679 (2,3); 2,3382 (0,56); 2,3336 (1 ,2); 2,3291 (1 ,62); 2,3245 (1 ,18); 2,3201 (0,56); 2,0741 (1 ,4); 1 ,2347

16-25 phenyl CH2 CH2 H (0,42); 0,0079 (0,73); -0,0002 (21 ,43); -0,0085 (0,68)

16-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

16-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

16-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

16-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

16-30 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 16-31 , Solvent: [DMSO], Spektrometer: 399.95MHz

16-31 2,4-dichlor-phenyl 0 CH2 CH2 H 8,3733 (2,22); 8,3598 (4,25); 8,3462 (2,16); 7,86

83-

Physikalische Daten: H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(0,36); 7,8499 (15,75); 7,8445 (16); 7,5726 (12,99) 7,5662 (13,73); 7,384 (6,39); 7,3775 (5,95); 7,3618 (8,64); 7,3553 (8,26); 7,2427 (13,19); 7,2204 (9,71) 6,9724 (15,47); 6,9669 (15,42); 4,1933 (6,84); 4,1785 (15,69); 4,1637 (7,42); 3,6023 (3,82); 3,5879 (10,74) 3,5736 (10,31); 3,5589 (3,38); 3,436 (0,35); 3,4093 (0,69); 3,4051 (0,73); 3,3396 (959,26); 3,2777 (0,41) 2,7117 (2,2); 2,6808 (0,6); 2,6764 (1,24); 2,6719

(1,72); 2,6673 (1,28) 2,6629 (0,63); 2,5923 (0,34) 2,5917 (0,32); 2,5901 (0,34); 2,5894 (0,37); 2,5887 (0,37); 2,5872 (0,43); 2,5865 (0,45); 2,5857 (0,48) 2,585 (0,51); 2,5843 (0,49); 2,5836 (0,51); 2,5828 (0,51); 2,5821 (0,55) 2,5813 (0,57); 2,5806 (0,59)

2,5799 (0,62); 2,5792 (0,61); 2,5784 (0,6); 2,5776 (0,63); 2,5769 (0,68); 2,5762 (0,72); 2,5754 (0,78) 2,5747 (0,82); 2,574 (0,86); 2,5732 (0,91); 2,5725 (0,97); 2,5718 (1,02); 2,5711 (1,04) 2,5703 (1,1) 2,5695 (1,16); 2,5688 (1,25); 2,5673 (1,48); 2,5666 (1,53); 2,5659 (1,58); 2,5652 (1,61); 2,5644 (1,68) 2,5637 (1,76); 2,5629 (1,85); 2,5622 (1,97); 2,5615 (2,05); 2,5607 (2,19); 2,56 (2,33); 2,557 (3,34); 2,5422 (584,06); 2,5297 (3,19); 2,5288 (3,16); 2,5252 (5,64); 2,5204 (7,98); 2,5118 (94,43); 2,5073 (193,88); 2,5028 (258,34); 2,4982 (189,27); 2,4937 (92,45); 2,4574 (0,45); 2,45 (0,35); 2,3679 (2,2); 2,3386 (0,59); 2,334 (1,21); 2,3295 (1,68); 2,325 (1,24); 2,3206 (0,6); 2,0747 (1,55); 1,2344 (0,47); 0,008 (0,67); -0,0002 (21,1); -0,0085 (0,66)

Verbindung Nr. 16-32, Solvent: [DMSO], Spektrometer: 399.95MHz 8,1773 (1,42); 8,1639 (2,61); 8,15 (1,41); 7,8358 (10,11); 7,8305 (10,24); 7,3511 (0,99); 7,3448 (9,12); 7,3401 (3,33); 7,3289 (4,09); 7,3238 (16); 7,3179 (2,23); 7,2713 (2,03); 7,2655 (13,71); 7,2608 (4); 7,249 (2,94); 7,2445 (8,01); 6,9468 (10,55); 6,9414 (10,43); 3,3385 (536,7); 3,3096 (1,12); 3,2151 (2,67); 3,1978 (5,58); 3,1828 (5,47); 3,1656 (2,73); 2,7119 (1,51); 2,6805 (0,44); 2,6762 (0,86); 2,6718 (1,17); 2,6672 (0,87); 2,6627 (0,47); 2,6287 (4,63); 2,61 (6,98); 2,5905 (5,12); 2,5634 (1,36); 2,5421 (349,18); 2,5249 (3,9); 2,5202 (5,31); 2,5116 (64,09); 2,5072 (129,58); 2,5027 (170,72); 2,4981 (123,82); 2,4936 (59,92); 2,3681 (1,5); 2,3386 (0,38); 2,3338 (0,78); 2,3294

16-32 4-chlor-phenyl CH2 CH2 CH2 H (1,1); 2,3249 (0,8); 2,3204 (0,38); 2,0744 (0,95);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

1 ,8097 (1 ,4); 1 ,7909 (3,79); 1 ,7726 (5,13); 1 ,7543 (3,55); 1 ,7361 (1 ,22); 0,008 (0,5); -0,0002 (14,61 ); - 0,0085 (0,44)

16-33 4-chlor-phenyl NCH3 CH2 CH2 H

16-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

16-35 4-chlor-phenyl CH(OCH3) CH2 - H

16-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 16-37, Solvent: [DMSO], Spektrometer: 399.95MHz 8,3333 (1 ,5); 8,3197 (2,75); 8,306 (1 ,49); 7,8428 (1 1 ,37); 7,8374 (1 1 ,56); 7,3489 (5,55); 7,3459 (5,79); 7,3362 (6,08); 7,3332 (6,06); 6,97 (4,65); 6,9615 (6,42); 6,9573 (4,87); 6,9494 (16); 6,9442 (1 1 ,98); 6,9141 (5,3); 6,91 18 (5,59); 6,9058 (4,12); 6,9033 (3,93); 3,4524 (2,97); 3,4348 (6,31 ); 3,4202 (6,3); 3,4019 (3,87); 3,3385 (606,52); 3,2723 (0,34); 3,0423 (5,38); 3,0244 (9,21 ); 3,0062 (4,53); 2,71 15 (1 ,81 ); 2,6804 (0,49); 2,6761 (0,92); 2,6714 (1 ,26); 2,6668 (0,96); 2,6623 (0,46); 2,5816 (0,53); 2,5418 (450,33); 2,5248 (4,92); 2,5198 (6,94); 2,51 13 (72,47); 2,5069 (145,82); 2,5023 (192,46); 2,4978 (140,37); 2,4933 (68,41 ); 2,4648 (0,44); 2,3677 (1 ,83); 2,3378 (0,46); 2,3336 (0,92); 2,3291 (1 ,26); 2,3245 (0,93); 2,3203 (0,44); 2,0742 (1 ,14); 1 ,2349 (0,33); 0,008 (0,55); - 0,0002 (15,05); -0,0085 (0,47)

16-37 2-thienyl CH2 CH2 H

16-38 3-thienyl CH2 CH2 - H

16-39 2-furyl CH2 CH2 - H

16-40 3-furyl CH2 CH2 - H

16-41 phenyl CH2 CH2 CH(CH3) H

16-42 phenyl CH2 CH2 CH2 H

16-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

16-44 4-t-butyl-phenyl CH2 CH2 CH2 H

16-45 4-methyl-phenyl CH2 CH2 CH2 H

16-46 phenyl CH2 CH2 CH(CH2CH3) H

16-47 2-methoxy-phenyl CH2 CH2 CH2 H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

16-48 2-methyl-phenyl CH2 CH2 CH2 H

16-49 3 -methyl-phenyl CH2 CH2 CH2 H

16-50 3-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 16-51 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,2182 (2,22); 8,2044 (4,08); 8, 1906 (2, 17); 7,8341 (15,73); 7,8287 (15,8); 7,3471 (1 ,34); 7,3303 (2,93); 7,3263 (2,69); 7,3094 (5,7); 7,2921 (2,82); 7,2886 (3,74); 7,2717 (1 ,73); 7, 1015 (0,79); 7,0971 (1 , 1 ); 7,0843 (7,57); 7,0642 (12,49); 7,0523 (1 ,65); 7,0442 (6,45); 7,0309 (0,93); 7,0279 (0,75); 6,9483 (0,37); 6,9424 (0,46); 6,932 (16); 6,9266 (15,81 ); 3,4196 (0,58); 3,4076 (0,7); 3,3386 (937,56); 3,2759 (0,66); 3,2628 (0,42); 3,2413 (3,79); 3,224 (7,25); 3,2077 (7,21 ); 3, 1906 (3,91 ); 2,712 (2,62); 2,6809 (5,78); 2,6715 (3,71 ); 2,6622 (9, 18); 2,6424 (5,7); 2,6247 (0,5); 2,6126 (0,44); 2,5961 (0,57); 2,5422 (618, 1 ); 2,5252 (6, 1 3); 2,51 18 (105,87); 2,5073 (213, 18); 2,5028 (280,32); 2,4982 (202,97); 2,4938 (97,9); 2,4472 (0,34); 2,3682 (2,59); 2,3384 (0,65); 2,3341 (1 ,33); 2,3295 (1 ,8); 2,3251 (1 ,31 ); 2,3206 (0,63); 2,2923 (0,32); 2,0747 (1 ,6); 1 ,78 (2); 1 ,7608 (5,09); 1 ,7425 (7,44); 1 ,7236 (4,71 ); 1 ,7051 (1 ,8); 1 ,2345 (0,42); 0,0079 (0,79); -0,0002 (23,26); -0,0085 (0,71 )

16-51 2,6-difluor-phenyl CH2 CH2 CH2 H

16-52 4-chlor-phenyl CH2 CH2 CH2 H

16-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

16-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

16-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

16-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

16-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

16-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

16-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

16-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

16-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

16-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ² L ³ Y Patent-Nr.

16-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

16-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

16-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

16-66 4-phenoxy-phenyl CH2 CH2 CH2 H

16-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

16-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

16-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

16-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

16-71 4-methoxy-phenyl CH2 CH2 CH2 H

16-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

16-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

16-74 4-fluor-phenyl CH2 CH2 CH2 H

16-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

16-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

16-77 2-chlor-phenyl CH2 CH2 CH2 H

16-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Verbindung Nr. 16-79, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,2073 (1 ,93); 8,1941 (3,6); 8,1808 (2,04); 7,8384 (15,02); 7,833 (15,64); 7,8221 (0,46); 7,3214 (6,94); 7,3184 (7,71 ); 7,3087 (7,78); 7,3057 (8,14); 6,9602 (15,15); 6,9547 (16); 6,9437 (8,41 ); 6,9394 (6,31 ); 6,9309 (7,83); 6,8888 (6,85); 6,8864 (7,42); 6,8805 (5,63); 6,878 (5,58); 3,341 (1030,45); 3,2639 (4,41 ); 3,2468 (8,81 ); 3,2317 (8,63); 3,2146 (4,53); 2,8573 (6,66); 2,8384 (1 1 ,53); 2,8193 (7,14); 2,7939 (0,36); 2,71 17 (2,58); 2,6762 (1 ,48); 2,6716 (1 ,94); 2,6671 (1 ,44); 2,6627 (0,77); 2,5421 (615,56); 2,525 (6,62); 2,51 15 (104,57); 2,5071 (21 1 ,52); 2,5026 (280,05); 2,498 (204,18); 2,4935 (99,35); 2,3679 (2,48); 2,3338 (1 ,29); 2,3294 (1 ,78); 2,3248 (1 ,31 ); 2,2928 (0,39); 2,0743 (1 ,56); 1 ,8699 (2,26); 1 ,8513 (6,3); 1 ,8328 (8,29); 1 ,8147 (6); 1 ,7965 (2, 1 ); 1 ,2348 (0,46); 0,008

16-79 2-thienyl CH2 CH2 CH2 H (0,76); -0,0001 (20,6); -0,0085 (0,59)

Verbindung Nr. 16-80, Solvent: [DMSO],

Spektrometer: 601.6MHz

16-80 4-chlor-2-thienyl CH2 CH2 H 8,3297 (1 ,84); 8,3205 (3,48); 8,31 1 1 (1 ,83); 7,842

Tabelle 17

Verbindungen der Formel 1-17

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

17-1 3 -methyl-2-thienyl CH2 CH2 - H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

Verbindung Nr. 17-2, Solvent: [DMSO], Spektrometer: 399.95MHz 8,17 (2,06); 8, 156 (3,99); 8,1419 (2,02); 7,9082 (15,62); 7,903 (15,74); 7,5666 (8,93); 7,5614 (9,26); 7,4288 (6,04); 7,4081 (13,21 ); 7,3941 (0,33); 7,38 (8,59); 7,3747 (7,99); 7,3593 (3,77); 7,354 (3,73); 6,8835 (0,33); 6,8734 (16); 6,8681 (15,76); 3,5158 (0,64); 3,3468 (21 ,57); 3,2552 (3,13); 3,238 (6,82); 3,2229 (6,82); 3,2056 (3, 19); 2,7416 (5,76); 2,723 (7,22); 2,703 (6,2); 2,676 (0,33); 2,5461 (50, 15); 2,5294 (0,61 ); 2,5246 (0,91 ); 2,5159 (1 1 ,4); 2,51 14 (23,3); 2,5068 (31 ,17); 2,5021 (22,71 ); 2,4976 (10,75); 1 ,8075 (1 ,66); 1 ,7887 (4,29); 1 ,7703 (5,72); 1 ,752 (4,03); 1 ,7335 (1 ,48); -0,0002 (3,44)

17-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz

8.2153 (0.36); 7.9050 (0.97); 7.8998 (0.97); 7.3625 (0.89); 7.3416 (1.44) 7.2769 (1.35); 7.2559 (0.85); 6.8470 (0.97); 6.8418 (0.97); 3.4907 (16.00) 3.4304 (0.43); 3.4133 (0.64); 3.3952 (0.63); 3.3796 (0.36); 2.8214 (0.50) 2.8027 (0.81); 2.7848 (0.45); 2.5552 (2.54); 2.5209 (1.35); 2.5165 (1.79)

17-3 4-chlor-phenyl CH2 CH2 H 2.5121 (1.37)

Verbindung Nr. 17-4, Solvent: [DMSO], Spektrometer: 399.95MHz 8,2259 (1 ,64); 8,21 18 (3,23); 8,1976 (1 ,63); 7,8966 (9,93); 7,8914 (10,05); 7,5854 (5,98); 7,582 (6,61 ); 7,3878 (1 ,24); 7,3834 (0,84); 7,3672 (9,54); 7,3621 (16); 7,3481 (0,42); 7,3404 (1 ,25); 6,8333 (10); 6,8281 (9,95); 5,7559 (1 ,39); 3,4479 (2,31 ); 3,431 1 (5,33); 3,4153 (5,28); 3,3981 (2,6); 3,3352 (133,8); 2,9377 (4,89); 2,9197 (8,43); 2,9022 (4,3); 2,5262 (1 ,13); 2,513 (17,16); 2,5085 (33,81 ); 2,504 ( ₄₄ ,7) _; 2,4994 (33,06); 2,495 (16,26); 1 ,9898 (0,89); 1 ,2497 (0,4); 1 , 1757 (0,5); -0,0002 (3,15)

17-4 2,4-dichlor-phenyl CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz

7.9346 (1.29); 7.9132 (1.34); 7.8986 (3.17); 7.8935 (3.16); 7.8787 (3.81) 7.8736 (3.79); 7.7754 (1.06); 7.7551 (1.08); 7.4397 (3.09); 7.4182 (5.40) 7.3952 (5.46); 7.3336 (4.88); 7.3125 (3.00); 7.2906 (3.65); 7.2696 (2.79) 6.9125 (3.03); 6.9073 (2.99); 6.8343 (3.71); 6.8291 (3.66); 4.3054 (1.47) 4.2903 (1.95); 4.2506 (1.89); 4.2351 (2.29); 4.2212 (0.50); 4.2041 (0.70) 4.1850 (0.65); 4.1687 (0.39); 4.0859 (0.54); 4.0694 (0.82); 4.0650 (0.67) 4.0527 (0.62); 4.0483 (0.81); 4.0319 (0.50); 3.3646 (214.06); 3.1876 (16.00); 3.1570 (13.27); 2.5446 (23.99); 2.5274 (0.78); 2.5141 (16.57) 2.5098 (32.70); 2.5053 (42.93); 2.5008 (32.15); 2.4965 (16.12); 1.1261

17-5 4-chlor-phenyl CH(0CH3) CH(CH3) H (6.08); 1.1092 (6.08); 0.9615 (4.80); 0.9444 (4.80); -0.0002 (5.26)

17-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz

8.1462 (1.98); 8.1321 (3.29); 8.1 178 (1.61); 7.9073 (0.57); 7.9023 (0.70);

17-7 4-chlor-phenyl CH(CH3) CH2 H 7.8892 (10.09); 7.8840 (9.22); 7.3662 (8.69); 7.3614 (3.54); 7.3497 (5.91);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.3449 (13.90); 7.3390 (2.04); 7.2904 (13.43); 7.2856 (4.05); 7.2735 (4.00) 7.2692 (7.52); 6.8214 (9.19); 6.8162 (8.32); 3.3817 (2.45); 3.3590 (43.45) 3.3418 (3.25); 3.3234 (4.50); 3.3080 (4.52); 3.2889 (2.72); 3.2744 (0.78) 3.2705 (0.79); 3.2561 (0.61); 3.0661 (0.45); 3.0486 (1.60); 3.0308 (2.90) 3.0130 (2.69); 2.9952 (1.22); 2.5650 (0.87); 2.5468 (23.00); 2.5162 (8.64) 2.5120 (14.46); 2.5075 (17.35); 2.5030 (12.20); 2.4987 (5.59); 2.0801 (0.53); 1.2175 (16.00); 1.2000 (14.95); -0.0002 (1.94)

[DMSO], Spektrometer: 399.95MHz

8.1758 (1.77); 8.1613 (3.49); 8.1473 (1.75); 7.8860 (10.63); 7.8808 (10.75) 7.5603 (7.55); 7.5551 (8.06); 7.4693 (4.38); 7.4482 (10.22); 7.4326 (0.35) 7.4228 (6.21); 7.4175 (5.75); 7.4017 (2.58); 7.3964 (2.55); 6.8132 (9.78) 6.8079 (9.75); 3.5263 (1.20); 3.5088 (2.78); 3.4916 (3.14); 3.4744 (1.94) 3.4651 (1.63); 3.4505 (1.57); 3.4331 (2.82); 3.4176 (2.76); 3.4003 (1.59) 3.3809 (1.92); 3.3657 (3.32); 3.3534 (31.95); 3.3342 (1.68); 3.3171 (0.90) 2.5478 (30.07); 2.5310 (0.41); 2.5260 (0.57); 2.5174 (6.98); 2.5131 (14.06) 2.5085 (18.69); 2.5040 (14.09); 2.4997 (7.17); 2.0819 (0.45); 1.209C

17-8 2,4-dichlor-phenyl CH(CH3) CH2 H (16.00); 1.1921 (15.93); -0.0002 (1.94)

[DMSO], Spektrometer: 399.95MHz

7.9341 (3.31); 7.9135 (3.39); 7.8967 (10.25); 7.8916 (10.27); 7.3383 (8.48) 7.3337 (3.34); 7.3218 (4.35); 7.3172 (14.38); 7.2595 (13.04); 7.2384 (7.87) 6.8857 (9.59); 6.8805 (9.52); 4.1614 (0.73); 4.1429 (1.62); 4.1255 (2.26) 4.1083 (1.70); 4.0898 (0.77); 3.3513 (29.33); 2.8463 (1.85); 2.8271 (1.84) 2.8129 (3.17); 2.7937 (3.09); 2.7358 (3.12); 2.7198 (3.22); 2.7023 (1.91) 2.6863 (1.79); 2.5461 (5.63); 2.5292 (0.35); 2.5156 (7.20); 2.51 13 (14.43) 2.5068 (19.08); 2.5022 (14.38); 2.4980 (7.33); 1.1269 (16.00); 1.1 103

17-9 4-chlor-phenyl CH2 CH(CH3) H (15.91); -0.0002 (1.86)

17-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz

7.8855 (3.71); 7.8804 (3.81); 7.8730 (0.69); 7.8567 (1.17); 7.8411 (0.58) 7.4474 (0.35); 7.4411 (2.83); 7.4360 (1.12); 7.4244 (1.45); 7.4192 (5.07) 7.4129 (0.85); 7.3742 (0.75); 7.3679 (5.04); 7.3629 (1.50); 7.3510 (1.08) 7.3460 (2.83); 6.8181 (3.59); 6.8129 (3.58); 3.3884 (3.34); 3.3724 (3.35) 3.3506 (6.88); 2.5459 (7.32); 2.5154 (2.28); 2.51 1 1 (4.56); 2.5066 (6.03)

17-11 4-chlor-phenyl C(CH3)2 CH2 H 2.5021 (4.54); 2.4980 (2.31); 1.2846 (16.00); -0.0002 (0.52)

[DMSO], Spektrometer: 399.95MHz

7.8724 (3.99); 7.8673 (4.35); 7.8503 (1.31); 7.8345 (0.64); 7.5338 (2.43) 7.5281 (2.59); 7.4753 (1.85); 7.4536 (2.70); 7.3702 (1.69); 7.3644 (1.63) 7.3486 (1.18); 7.3428 (1.13); 6.7823 (3.77); 6.7771 (3.77); 3.7319 (3.38) 3.7159 (3.35); 3.3496 (8.21); 2.5471 (10.07); 2.5166 (2.36); 2.5123 (4.73)

17-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 2.5078 (6.26); 2.5033 (4.73); 2.4992 (2.42); 1.4336 (16.00); -0.0002 (0.46)

[DMSO], Spektrometer: 399.95MHz

8.2730 (3.03); 8.2592 (5.74); 8.2452 (3.03); 7.9069 (15.65); 7.9018 (16.00) 7.4453 (6.1 1); 7.4414 (5.58); 7.4270 (7.86); 7.4226 (7.88); 7.4054 (0.35)

17-13 2-chlor-phenyl CH2 CH2 H 7.3586 (4.31); 7.3532 (5.37); 7.3400 (7.02); 7.3354 (9.00); 7.3203 (0.55)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.3104 (2.79); 7.3064 (3.62); 7.2922 (8.16); 7.2882 (7.83); 7.2770 (8.74) 7.2751 (8.85); 7.2712 (9.60); 7.2588 (6.59); 7.2536 (5.94); 7.2404 (2.24) 7.2355 (1.85); 6.8678 (15.76); 6.8626 (15.98); 3.4600 (4.27); 3.4436 (8.81) 3.4274 (8.22); 3.4242 (8.90); 3.4090 (4.93); 3.3540 (25.43); 2.9612 (8.94) 2.9420 (13.13); 2.9244 (7.88); 2.5472 (38.06); 2.5301 (0.65); 2.5124 (18.26); 2.5080 (24.12); 2.5035 (18.65); 2.081 1 (0.64); -0.0002 (1.98)

Verbindung Nr. 1 7-14, Solvent: [DMSO], Spektrometer: 399.95MHz 8, 1863 (2,74); 8, 1 724 (5,32); 8, 1584 (2,79); 7,9015 (15,73); 7,8963

(15.92) ; 7,5632 (0,34); 7,5532 (12,94); 7,5433 (0,69); 7,5327 (14,85); 7,5167 (12,06); 7,51 18 (12,61 ); 7,2422 (7,04); 7,2372 (6,94); 7,2216 (6,22); 7,2166 (6, 15); 6,8352 (16); 6,8299 (15,99); 5,7581 (3,62); 3,4468 (3,88); 3,4296 (9,23); 3,4144 (9,26); 3,3972 (4,27); 3,3301

(14.93) ; 2,8348 (7,68); 2,817 (14,34); 2,7994 (6,95); 2,5273 (0,91 ); 2,51 39 (15,91 ); 2,5096 (31 ,41 ); 2,505 (41 ,48); 2,5005 (30,86); 2,4962

17-14 3 ,4-dichlor-phenyl CH2 CH2 H (15,39); 1 ,9909 (0,36); 1 ,3379 (0,44); 1 ,25 (0,54); -0,0002 (2,91 )

Verbindung Nr. 1 7-15, Solvent: [DMSO], Spektrometer: 399.95MHz 8, 1892 (1 ,68); 8, 1 751 (3, 1 3); 8, 1612 (1 ,62); 7,9024 (9,49); 7,8973 (9,57); 7,4372 (3,64); 7,4325 (7, 1 7); 7,4277 (4, 15); 7,3257 (0,45); 7,3109 (16); 7,3062 (15,6); 6,8462 (0,45); 6,841 (0,52); 6,8277 (9,35); 6,8225 (9,31 ); 3,4538 (2,27); 3,4366 (5,62); 3,4216 (5,74); 3,4045 (2,62); 3,3236 (18,65); 2,8444 (4,43); 2,8268 (8,57); 2,8093 (4,05); 2,6719 (0,42); 2,5251 (1 ,34); 2,51 15 (21 ,91 ); 2,5072 (42,99); 2,5027 (56,75); 2,4982 (42,05); 2,4939 (20,75); 2,3296 (0,37); 1 ,3363 (0,39);

17-15 3,5- dichlor-pheny 1 CH2 CH2 H 1 ,2496 (0,48); -0,0002 (3,95)

[DMSO], Spektrometer: 399.95MHz

8.2249 (2.76); 8.21 1 1 (5.34); 8.1973 (2.89); 7.9082 (15.77); 7.9031 (16.00) 7.3626 (0.46); 7.3478 (3.64); 7.3419 (1.08); 7.3285 (9.45); 7.3152 (U .43) 7.3100 (14.43); 7.2796 (7.56); 7.2629 (3.23); 7.2581 (3.52); 7.2126 (7.54) 7.1938 (5.32); 6.8562 (15.88); 6.8510 (15.93); 3.4459 (3.89); 3.4290 (8.27) 3.41 12 (8.16); 3.3953 (4.50); 3.3551 (29.48); 2.8405 (7.57); 2.8220 (12.55) 2.8041 (7.01); 2.7848 (0.33); 2.5467 (37.80); 2.5302 (0.53); 2.51 18 (17.03)

17-16 3-chlor-phenyl CH2 CH2 H 2.5074 (22.52); 2.5029 (17.23); 2.0805 (0.60); -0.0002 (1.57)

[DMSO], Spektrometer: 399.95MHz

8.2765 (2.49); 8.2625 (4.74); 8.2484 (2.48); 7.9060 (15.79); 7.9008 (16.00) 7.3334 (2.38); 7.3295 (2.94); 7.3148 (4.61); 7.3105 (6.26); 7.3033 (1.99) 7.2983 (2.42); 7.2908 (4.50); 7.2847 (3.66); 7.2698 (3.00); 7.2645 (4.26) 7.2601 (2.35); 7.2507 (2.44); 7.2463 (1.93); 7.1821 (4.50); 7.1585 (10.87) 7.1415 (8.18); 7.1388 (9.95); 7.1233 (3.36); 7.1205 (2.96); 6.8587 (14.47) 6.8534 (14.58); 3.4380 (3.67); 3.4216 (7.24); 3.4051 (6.62); 3.4017 (7.33) 3.3865 (4.13); 3.3538 (21.37); 2.8670 (6.33); 2.8483 (9.90); 2.8300 (5.64) 2.5471 (40.41); 2.5304 (0.47); 2.5255 (0.62); 2.5167 (7.78); 2.5124 (15.88)

17-17 2-fluor-phenyl CH2 CH2 H 2.5078 (21.29); 2.5033 (16.19); 2.4991 (8.35); 2.0807 (0.44); -0.0002 (1.98)

[DMSO], Spektrometer: 399.95MHz

17-18 2,6-difluor-phenyl CH2 CH2 - H 8.3342 (2.88); 8.3196 (5.58); 8.3051 (2.87); 7.9026 (15.84); 7.8975 (16.00);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.3664 (1.21); 7.3493 (2.96); 7.3460 (2.91); 7.3287 (5.48); 7.3081 (3.63) 7.2912 (1.61); 7.1040 (1.12); 7.0917 (8.22); 7.0720 (12.64); 7.0609 (2.02) 7.0523 (6.99); 7.0393 (1.04); 6.8308 (15.75); 6.8256 (15.91); 3.4058 (3.86) 3.3893 (8.82); 3.3709 (8.98); 3.3545 (32.02); 2.8820 (6.36); 2.8638 (10.95) 2.8461 (5.71); 2.5491 (41.65); 2.5323 (0.55); 2.5142 (16.83); 2.509S (22.31); 2.5054 (17.15); 2.0827 (0.67); -0.0002 (1.48)

[DMSO], Spektrometer: 399.95MHz

8.3288 (1.55); 8.3145 (3.12); 8.3000 (1.57); 7.8978 (9.08); 7.8927 (9.37) 7.4685 (1 1.72); 7.4484 (16.00); 7.3046 (5.36); 7.2854 (5.37); 7.2835 (5.45) 7.2643 (3.55); 6.8498 (9.10); 6.8446 (9.27); 3.4357 (1.95); 3.4193 (4.69) 3.4001 (4.74); 3.3850 (2.68); 3.3443 (255.13); 3.3124 (0.63); 3.1460 (4.54) 3.1268 (6.78); 3.1098 (3.60); 2.6771 (0.46); 2.6727 (0.64); 2.6681 (0.49) 2.5429 (48.46); 2.5260 (1.90); 2.5124 (34.75); 2.5080 (70.93); 2.5035 (95.37); 2.4990 (72.98); 2.4948 (38.02); 2.3347 (0.46); 2.3303 (0.64)

17-19 2,6-dichlor-phenyl CH2 CH2 H 2.3259 (0.48); 2.0770 (0.45); -0.0002 (2.21)

[DMSO], Spektrometer: 399.95MHz

8.2350 (2.48); 8.2211 (4.60); 8.2072 (2.38); 7.9189 (0.55); 7.9089 (14.27) 7.9037 (14.51); 7.6742 (0.38); 7.6541 (0.53); 7.5885 (10.40); 7.5657 (7.60) 7.5527 (16.00); 7.5341 (3.06); 7.5164 (0.99); 7.4822 (0.46); 7.4624 (0.43) 6.8563 (0.76); 6.8452 (13.05); 6.8400 (13.21); 3.4790 (3.41); 3.4619 (7.67) 3.4465 (7.57); 3.4288 (3.97); 3.3577 (26.92); 2.9395 (6.60); 2.9214 (1 1.46)

3 -(trifluormethyl)- 2.9036 (5.97); 2.5490 (41.45); 2.5323 (0.52); 2.5274 (0.63); 2.5185 (8.02)

2.5142 (16.31); 2.5097 (21.74); 2.5052 (16.57); 2.5010 (8.61); 2.0822

17-20 phenyl CH2 CH2 H (0.92); -0.0002 (1.78)

[DMSO], Spektrometer: 399.95MHz

8.2544 (2.57); 8.2406 (4.94); 8.2266 (2.54); 7.91 13 (15.88); 7.9061 (16.00); 7.6742 (10.65); 7.6540 (12.96); 7.4830 (12.41); 7.4629 (10.58); 6.8595 (13.45); 6.8543 (13.40); 3.4818 (3.52); 3.4648 (7.59); 3.4474 (7.40); 3.4313

4-(trifluormethyl)- (3.94); 3.3601 (18.84); 2.9325 (6.19); 2.9142 (10.62); 2.8963 (5.49); 2.5504

(41.32); 2.5337 (0.44); 2.5289 (0.58); 2.5201 (6.63); 2.5157 (13.54); 2.51 12

17-21 phenyl CH2 CH2 H (18.14); 2.5066 (13.67); 2.5023 (6.94); 2.0836 (1.04); -0.0002 (1.85)

[DMSO], Spektrometer: 399.95MHz

8.2893 (0.78); 8.2753 (1.48); 8.2612 (0.77); 7.9142 (4.40); 7.9091 (4.51) 7.1690 (1.52); 7.1570 (2.32); 7.1455 (4.19); 7.1396 (1.94); 7.1285 (3.49) 7.1242 (4.10); 7.1 147 (3.00); 7.1085 (1.64); 7.1054 (1.45); 7.1028 (1.43) 6.8805 (4.36); 6.8752 (4.36); 3.3764 (1.19); 3.3612 (2.28); 3.3566 (2.37) 3.3480 (8.87); 3.3377 (2.36); 3.3231 (1.32); 2.8169 (2.38); 2.8019 (2.00) 2.7969 (2.70); 2.7781 (2.12); 2.5442 (10.51); 2.5136 (3.09); 2.5093 (6.18)

17-22 2-methyl-phenyl CH2 CH2 H 2.5048 (8.22); 2.5003 (6.24); 2.4961 (3.22); 2.3238 (16.00); -0.0002 (1.07)

[DMSO], Spektrometer: 399.95MHz

8.3716 (0.56); 8.3571 (1.13); 8.3425 (0.56); 7.9246 (3.20); 7.9195 (3.24)

2,4,6-trimethyl- 6.8969 (3.16); 6.8916 (3.15); 6.8093 (5.25); 3.3493 (5.65); 3.2268 (0.63)

3.2122 (1.13); 3.1985 (1.13); 3.1914 (0.95); 3.1852 (1.19); 3.1712 (0.75)

17-23 phenyl CH2 CH2 H 2.7842 (1.35); 2.7708 (1.09); 2.7631 (1.36); 2.7581 (1.16); 2.7433 (1.14)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

2.5445 (14.01); 2.5140 (1.84); 2.5097 (3.72); 2.5052 (4.96); 2.5007 (3.75); 2.3013 (16.00); 2.1841 (8.24); -0.0002 (0.61)

[DMSO], Spektrometer: 399.95MHz

8.1934 (0.77); 8.1795 (1.52); 8.1655 (0.79); 7.9109 (4.42); 7.9057 (4.46); 6.8844 (4.25); 6.8791 (4.46); 6.8754 (3.05); 6.8548 (3.36); 6.8202 (2.95); 6.8155 (3.33); 6.7501 (1.89); 6.7454 (1.75); 6.7298 (1.41); 6.7250 (1.34); 3.7297 (16.00); 3.7147 (15.91); 3.4141 (0.94); 3.3979 (1.88); 3.3779 (1.94); 3.3621 (1.32); 3.3532 (6.27); 2.7580 (1.87); 2.7385 (2.73); 2.7207 (1.71);

3,4-bismethoxy- 2.5453 (1 1.49); 2.5149 (2.00); 2.5106 (4.07); 2.5061 (5.45); 2.5016 (4.16); -

17-24 phenyl CH2 CH2 H 0.0002 (0.64)

[DMSO], Spektrometer: 399.95MHz

8.2349 (2.45); 8.2211 (4.64); 8.2072 (2.45); 7.9072 (15.16); 7.9020 (15.41); 7.3229 (4.79); 7.3045 (12.58); 7.2862 (12.23); 7.2470 (16.00); 7.2285 (1 1.44); 7.2071 (6.59); 7.1926 (1.60); 7.1892 (2.35); 6.8730 (15.16); 6.8677 (15.29); 3.4314 (3.88); 3.4157 (6.90); 3.3985 (6.16); 3.3942 (7.30); 3.3793 (4.36); 3.3488 (27.85); 2.8251 (7.51); 2.8053 (10.01); 2.7873 (6.71); 2.5441 (33.83); 2.5272 (0.54); 2.5136 (9.76); 2.5093 (19.52); 2.5048 (25.88);

17-25 phenyl CH2 CH2 H 2.5003 (19.58); 2.4961 (10.02); 2.0776 (0.54); -0.0002 (3.28)

17-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

17-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

C(CH2-

17-28 4-chlor-phenyl CH2 CH2) H

C(CH2-

17-29 2,4-dichlor-phenyl CH2 CH2) H

17-30 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 1 7-31 , Solvent: [DMSO], Spektrometer: 399.95MHz 8,3198 (2,68); 8,3063 (5,28); 8,2928 (2,73); 7,919 (1 3, 1 3); 7,91 39 (1 3,58); 7,5705 (1 1 ,09); 7,5641 (12, 19); 7,3831 (5,65); 7,3766 (5,45); 7,3609 (7,7); 7,3545 (7,63); 7,2428 (12,91 ); 7,2205 (9,58); 6,9026 (13,27); 6,8974 (1 3,37); 4, 1934 (7, 15); 4, 1785 (16); 4, 1638 (7,93); 3,6025 (3,89); 3,5881 (10,79); 3,5737 (10,5); 3,5591 (3,6); 3,3328 (59,36); 2,71 36 (0,32); 2,5439 (68,35); 2,5274 (1 ,08); 2,509 (33, 15); 2,5046 (44,31 ); 2,5002 (34,03); 2,3703 (0,33); -0,0002 (1 ,74)

17-31 2,4-dichlor-phenyl 0 CH2 CH2 H

17-32 4-chlor-phenyl CH2 CH2 CH2 H

17-33 4-chlor-phenyl NCH3 CH2 CH2 H

17-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

17-35 4-chlor-phenyl CH(OCH3) CH2 - H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

17-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

[DMSO], Spektrometer: 399.95MHz

8.2894 (2.91); 8.2758 (5.41); 8.2620 (2.89); 7.91 17 (15.02); 7.9066 (14.86) 7.7491 (0.38); 7.7366 (0.42); 7.7308 (0.43); 7.7212 (0.44); 7.3494 (7.92) 7.3467 (7.79); 7.3367 (8.65); 7.3340 (8.01); 7.1526 (0.35); 7.1430 (0.39) 6.9710 (6.64); 6.9625 (9.30); 6.9585 (7.00); 6.9498 (8.54); 6.9151 (9.96) 6.9070 (7.48); 6.8780 (16.00); 6.8728 (15.62); 3.4726 (0.57); 3.4472 (4.55) 3.4297 (9.92); 3.4147 (10.07); 3.3965 (5.26); 3.3313 (1 11.52); 3.067C (0.51); 3.0409 (9.27); 3.0226 (15.47); 3.0045 (7.69); 2.6758 (0.66); 2.6713 (0.85); 2.6671 (0.63); 2.5067 (96.28); 2.5024 (121.05); 2.4980 (87.99) 2.3290 (0.81); 2.3246 (0.60); 1.3974 (3.19); 0.0078 (1.41); -0.0002 (26.06)

17-37 2-thienyl CH2 CH2 H -0.0084 (1.01)

17-38 3-thienyl CH2 CH2 - H

17-39 2-furyl CH2 CH2 - H

17-40 3-furyl CH2 CH2 - H

[DMSO], Spektrometer: 399.95MHz

7.9127 (9.50); 7.9076 (9.66); 7.8923 (3.15); 7.8716 (3.10); 7.2928 (3.1 1) 7.2742 (8.22); 7.2560 (7.67); 7.2169 (9.97); 7.1996 (5.58); 7.1882 (2.37) 7.1850 (2.88); 7.1671 (4.16); 7.1525 (1.07); 7.1492 (1.57); 6.9296 (9.21) 6.9244 (9.27); 3.9844 (0.63); 3.9644 (1.41); 3.9487 (1.90); 3.9328 (1.47) 3.9127 (0.67); 3.3512 (9.38); 2.6692 (0.44); 2.6533 (0.55); 2.6454 (0.47) 2.6346 (1.92); 2.6197 (3.59); 2.61 13 (2.75); 2.6028 (2.93); 2.5963 (3.75) 2.5804 (2.06); 2.5688 (0.52); 2.5629 (0.67); 2.5442 (27.24); 2.5274 (0.48) 2.5134 (7.30); 2.5093 (14.43); 2.5048 (18.94); 2.5003 (14.42); 1.8535 (0.47); 1.8371 (0.61); 1.8313 (0.86); 1.8196 (1.20); 1.8100 (0.88); 1.8042 (1.22); 1.7971 (1.74); 1.7821 (1.43); 1.7765 (1.30); 1.7605 (1.65); 1.7444 (1.58); 1.7364 (1.1 1); 1.7292 (1.54); 1.7217 (1.54); 1.7096 (1.05); 1.7053 (1.30); 1.6957 (0.64); 1.6887 (0.68); 1.6722 (0.41); 1.1507 (16.00); 1.1341

17-41 phenyl CH2 CH2 CH(CH3) H (15.91); -0.0002 (2.95)

[DMSO], Spektrometer: 399.95MHz

8.1368 (2.49); 8.1231 (4.66); 8.1094 (2.50); 7.9090 (14.35); 7.9038 (14.46); 7.3063 (4.74); 7.2877 (13.13); 7.2695 (12.50); 7.2351 (16.00); 7.2178 (8.62); 7.1973 (4.41); 7.1795 (6.60); 7.1616 (2.42); 6.8846 (14.75); 6.8794 (14.76); 3.3474 (19.82); 3.2286 (3.90); 3.21 14 (8.33); 3.1960 (8.33); 3.1853 (1.91); 3.1788 (4.15); 2.6414 (7.03); 2.6225 (10.63); 2.6029 (7.70); 2.5441 (42.85); 2.5275 (0.71); 2.5093 (22.43); 2.5048 (29.37); 2.5004 (22.20); 1.8273 (2.15); 1.8084 (5.85); 1.7900 (8.00); 1.7714 (5.53); 1.7531 (1.93); -

17-42 phenyl CH2 CH2 CH2 H 0.0002 (4.50)

[DMSO], Spektrometer: 399.95MHz

7.9294 (3.33); 7.9154 (10.19); 7.9102 (11.89); 7.4127 (3.68); 7.4094 (3.74) 7.3935 (4.75); 7.3900 (4.76); 7.3633 (2.79); 7.3589 (3.23); 7.3446 (4.33)

17-43 2-Cl-phenyl CH2 CH2 CH(CH3) H 7.3403 (4.71); 7.2924 (1.90); 7.2890 (2.15); 7.2741 (4.59); 7.2706 (4.36)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.2558 (2.99); 7.2519 (2.61); 7.2437 (3.44); 7.2388 (3.45); 7.2246 (3.72) 7.2200 (3.70); 7.2059 (1.49); 7.2014 (1.35); 6.9319 (9.09); 6.9267 (9.20) 4.0286 (0.72); 4.01 16 (1.55); 3.9926 (2.08); 3.9751 (1.67); 3.9575 (0.77) 3.3505 (12.19); 2.7561 (0.48); 2.7433 (2.36); 2.7376 (2.68); 2.7261 (3.82) 2.7159 (4.23); 2.7036 (2.81); 2.6978 (2.63); 2.6850 (0.55); 2.6768 (0.33) 2.5467 (22.42); 2.5297 (0.50); 2.5158 (6.75); 2.51 18 (13.34); 2.5073 (17.62); 2.5028 (13.49); 1.7964 (0.38); 1.7844 (1.32); 1.7755 (1.58); 1.765S (3.15); 1.7483 (3.08); 1.7459 (3.09); 1.7367 (2.84); 1.7262 (1.66); 1.7194 (1.44); 1.7086 (0.37); 1.1794 (16.00); 1.1628 (15.97); -0.0002 (2.80)

[DMSO], Spektrometer: 399.95MHz

8.1086 (0.61); 7.9056 (1.74); 7.9005 (1.76); 7.3061 (1.74); 7.2855 (2.27) 7.1515 (2.05); 7.1309 (1.61); 6.8779 (1.72); 6.8727 (1.74); 3.3462 (2.94) 3.2216 (0.43); 3.2046 (0.95); 3.1888 (0.95); 3.1719 (0.45); 2.5985 (0.77) 2.5797 (1.25); 2.5605 (0.84); 2.5442 (1.83); 2.5093 (2.63); 2.5049 (3.45) 2.5005 (2.61); 1.7923 (0.67); 1.7740 (0.91); 1.7556 (0.63); 1.2603 (16.00); -

17-44 4-t-butyl-phenyl CH2 CH2 CH2 H 0.0002 (0.55)

[DMSO], Spektrometer: 399.95MHz

8.1177 (0.84); 8.1040 (1.61); 8.0903 (0.85); 7.9061 (4.81); 7.9010 (4.85) 7.1 188 (1.26); 7.1127 (0.73); 7.0976 (11.87); 7.0932 (1 1.01); 7.0718 (1.22) 6.8801 (4.97); 6.8749 (4.98); 3.3461 (6.49); 3.2100 (1.25); 3.1929 (2.69) 3.1773 (2.70); 3.1602 (1.33); 2.5896 (2.25); 2.5708 (3.58); 2.5511 (2.73) 2.5438 (14.58); 2.5090 (7.74); 2.5046 (10.12); 2.5001 (7.69); 2.2601 (16.00); 1.7966 (0.68); 1.7777 (1.91); 1.7595 (2.63); 1.7409 (1.81); 1.7227

17-45 4-methyl-phenyl CH2 CH2 CH2 H (0.62); -0.0002 (1.63)

[DMSO], Spektrometer: 399.95MHz

7.9184 (8.52); 7.9133 (8.64); 7.7938 (3.22); 7.7719 (3.28); 7.2878 (3.07) 7.2691 (8.26); 7.2509 (7.54); 7.2127 (10.10); 7.1952 (5.70); 7.1806 (2.98) 7.1626 (4.18); 7.1447 (1.57); 6.9428 (8.82); 6.9377 (9.07); 3.8539 (1.00) 3.8401 (1.66); 3.8339 (1.41); 3.8198 (1.75); 3.8061 (0.98); 3.3471 (13.64) 2.6696 (0.69); 2.6524 (0.92); 2.6482 (0.87); 2.6349 (1.70); 2.6159 (2.42) 2.5958 (1.85); 2.5907 (1.82); 2.5685 (2.70); 2.5447 (23.34); 2.5097 (13.17) 2.5054 (17.07); 2.501 1 (13.39); 1.7774 (2.16); 1.7576 (4.32); 1.7388 (3.59) 1.7239 (1.48); 1.7170 (1.31); 1.5828 (0.69); 1.5686 (1.07); 1.5650 (1.06) 1.5493 (1.95); 1.5353 (1.66); 1.5305 (1.79); 1.5170 (1.55); 1.4940 (1.64) 1.4747 (2.32); 1.4557 (1.94); 1.4401 (1.34); 1.4213 (0.83); 0.8711 (7.89)

17-46 phenyl CH2 CH2 CH(CH2CH3) H 0.8527 (16.00); 0.8341 (7.15); -0.0002 (2.47)

[DMSO], Spektrometer: 399.95MHz

8.1191 (0.73); 8.1052 (1.39); 8.0914 (0.74); 7.9055 (3.72); 7.9003 (3.84) 7.1997 (0.68); 7.1959 (0.87); 7.1764 (1.97); 7.1702 (1.96); 7.1571 (1.61) 7.1515 (2.23); 6.9530 (2.31); 6.9330 (2.00); 6.8845 (4.80); 6.8793 (4.01) 6.8679 (2.33); 6.8494 (1.04); 3.7736 (16.00); 3.3485 (7.03); 3.2187 (0.99) 3.2016 (2.09); 3.1848 (2.13); 3.1682 (1.07); 2.6032 (1.84); 2.5844 (2.84) 2.5652 (2.04); 2.5445 (9.41); 2.5094 (5.94); 2.5051 (7.84); 2.5009 (6.13)

17-47 2-methoxy-phenyl CH2 CH2 CH2 H 1.7730 (0.53); 1.7537 (1.48); 1.7357 (2.10); 1.7168 (1.40); 1.6986 (0.49); -

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

0.0002 (0.98)

[DMSO], Spektrometer: 399.95MHz

8.1622 (0.78); 8.1484 (1.45); 8.1346 (0.77); 7.9092 (4.51); 7.9041 (4.61) 7.1697 (0.97); 7.1650 (1.27); 7.1475 (2.45); 7.1254 (2.49); 7.1218 (2.59) 7.11 19 (2.40); 7.0959 (3.43); 7.0908 (2.68); 7.0787 (1.31); 7.0746 (1.21) 7.0609 (0.43); 7.0568 (0.36); 6.8814 (4.59); 6.8763 (4.67); 3.3412 (12.1 1) 3.2653 (1.1 1); 3.2482 (2.59); 3.2328 (2.58); 3.2158 (1.19); 2.6194 (2.08) 2.6005 (2.71); 2.5803 (2.29); 2.5427 (15.63); 2.5258 (0.38); 2.5078 (13.05) 2.5033 (17.27); 2.4989 (13.26); 2.2571 (16.00); 1.7732 (0.61); 1.7544

17-48 2-methyl-phenyl CH2 CH2 CH2 H (1.62); 1.7357 (2.13); 1.7170 (1.52); 1.6987 (0.55); -0.0002 (2.60)

[DMSO], Spektrometer: 399.95MHz

8.1261 (0.87); 8.1 124 (1.65); 8.0986 (0.88); 7.9076 (4.97); 7.9024 (5.13) 7.1833 (1.42); 7.1646 (3.33); 7.1459 (2.14); 7.0322 (3.37); 7.0168 (2.30) 6.9972 (3.66); 6.9779 (1.70); 6.8828 (5.15); 6.8776 (5.29); 3.3453 (10.30) 3.2197 (1.29); 3.2025 (2.80); 3.1868 (2.80); 3.1699 (1.38); 2.5970 (2.32) 2.5781 (3.54); 2.5585 (2.58); 2.5436 (12.31); 2.5087 (8.59); 2.5042 (1 1.48) 2.4998 (8.92); 2.2758 (16.00); 1.81 1 1 (0.70); 1.7921 (1.94); 1.7738 (2.66)

17-49 3 -methyl-phenyl CH2 CH2 CH2 H 1.7551 (1.84); 1.7370 (0.65); -0.0002 (1.52)

[DMSO], Spektrometer: 399.95MHz

8.1375 (2.05); 8.1238 (3.89); 8.1 101 (2.08); 7.9127 (11.29); 7.9075 (1 1.48); 7.3386 (3.08); 7.3190 (16.00); 7.3000 (6.92); 7.2569 (5.46); 7.2366 (2.93); 7.2157 (5.86); 7.1966 (4.09); 6.8827 (1 1.57); 6.8775 (1 1.66); 3.3505 (14.94); 3.2206 (3.03); 3.2035 (6.85); 3.1881 (6.98); 3.1712 (3.18); 2.6569 (5.36); 2.6381 (8.51); 2.6187 (5.85); 2.5466 (34.1 1); 2.5298 (0.52); 2.51 17 (16.03); 2.5073 (20.99); 2.5029 (16.00); 1.8282 (1.62); 1.8096 (4.68);

17-50 3-chlor-phenyl CH2 CH2 CH2 H 1.791 1 (6.33); 1.7727 (4.47); 1.7546 (1.47); -0.0002 (2.94)

[DMSO], Spektrometer: 399.95MHz

8.1763 (2.84); 8.1625 (5.46); 8.1486 (2.86); 7.9383 (0.32); 7.9332 (0.36) 7.9093 (15.44); 7.9041 (15.62); 7.3514 (1.34); 7.3344 (3.16); 7.3310 (3.01) 7.3137 (5.89); 7.2930 (3.89); 7.2761 (1.74); 7.1232 (0.33); 7.1063 (0.84) 7.1021 (1.22); 7.0893 (8.41); 7.0694 (13.19); 7.0496 (6.96); 7.0360 (0.98) 6.8676 (15.70); 6.8624 (16.00); 6.5148 (0.56); 3.3516 (23.80); 3.2443 (3.92); 3.2273 (8.04); 3.2098 (8.05); 3.1934 (4.14); 2.6878 (5.86); 2.668S (9.90); 2.6494 (6.31); 2.5483 (49.22); 2.5313 (0.73); 2.5134 (22.83); 2.509C (30.10); 2.5046 (23.13); 2.0825 (0.49); 1.7846 (2.16); 1.7653 (5.68); 1.747C

17-51 2,6-difluor-phenyl CH2 CH2 CH2 H (8.12); 1.7281 (5.29); 1.7096 (1.91); -0.0002 (4.53)

[DMSO], Spektrometer: 399.95MHz

8.1353 (1.90); 8.1216 (3.60); 8.1078 (1.91); 7.9108 (10.72); 7.9057 (10.81); 7.3480 (9.46); 7.3434 (3.76); 7.3315 (4.99); 7.3269 (16.00); 7.2703 (14.47); 7.2492 (8.63); 6.8796 (10.90); 6.8744 (10.94); 3.3507 (15.76); 3.2175

(2.79) ; 3.2005 (6.27); 3.1852 (6.32); 3.1681 (2.92); 2.6374 (4.98); 2.6186

(7.80) ; 2.5992 (5.41); 2.5465 (32.60); 2.5296 (0.49); 2.51 17 (14.92); 2.5072 (19.57); 2.5028 (14.83); 1.8128 (1.51); 1.7942 (4.29); 1.7758 (5.78); 1.7573

17-52 4-chlor-phenyl CH2 CH2 CH2 H (4.06); 1.7392 (1.34); -0.0002 (3.23)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz

7.9701 (3.26); 7.9492 (3.32); 7.9137 (9.17); 7.9086 (9.30); 7.4476 (12.36) 7.4274 (16.00); 7.2717 (5.17); 7.2522 (5.98); 7.2315 (3.53); 6.9302 (9.18) 6.9251 (9.17); 4.1088 (0.72); 4.0919 (1.62); 4.0745 (1.94); 4.0552 (1.61) 4.0384 (0.74); 3.3437 (20.97); 2.9196 (0.41); 2.9041 (3.32); 2.8834 (6.19) 2.8696 (1.83); 2.8624 (3.70); 2.8464 (0.44); 2.5456 (27.97); 2.5285 (0.67) 2.5107 (23.37); 2.5062 (30.62); 2.5018 (23.06); 1.7293 (0.38); 1.7136 (1.61); 1.7077 (1.48); 1.6987 (2.26); 1.6902 (2.74); 1.6776 (2.43); 1.670C (2.57); 1.6574 (1.45); 1.6485 (1.28); 1.6332 (0.41); 1.2153 (15.51); 1.1986

17-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H (15.42); -0.0002 (4.88)

[DMSO], Spektrometer: 399.95MHz

7.9154 (9.25); 7.9103 (9.32); 7.8677 (3.43); 7.8470 (3.49); 7.3985 (3.80) 7.3942 (6.77); 7.3898 (4.20); 7.3043 (15.61); 7.2998 (14.40); 6.9135 (9.28) 6.9083 (9.30); 3.9652 (0.67); 3.9456 (1.43); 3.9297 (1.98); 3.9136 (1.53) 3.8938 (0.71); 3.3504 (12.26); 2.6914 (0.37); 2.6697 (0.64); 2.6568 (1.91) 2.6414 (3.71); 2.6339 (2.49); 2.6197 (3.97); 2.6028 (2.04); 2.5894 (0.69) 2.5680 (0.47); 2.5481 (23.90); 2.5310 (0.42); 2.5133 (13.84); 2.5089 (18.18); 2.5044 (13.87); 1.8187 (0.39); 1.8135 (0.60); 1.801 1 (1.23); 1.7803 (3.13); 1.7629 (3.66); 1.7503 (1.72); 1.7430 (2.69); 1.7261 (1.32); 1.7141

17-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H (0.46); 1.7070 (0.42); 1.1463 (16.00); 1.1297 (15.94); -0.0002 (2.95)

[DMSO], Spektrometer: 399.95MHz

8.2139 (0.48); 8.1999 (0.94); 8.1859 (0.48); 7.9149 (2.54); 7.9097 (2.55) 6.9585 (8.29); 6.8842 (2.65); 6.8790 (2.68); 3.3478 (3.48); 3.3182 (0.64) 3.3015 (1.64); 3.2862 (1.65); 3.2695 (0.66); 2.6167 (1.17); 2.6033 (0.97) 2.5962 (1.23); 2.5881 (0.97); 2.5752 (1.26); 2.5441 (6.22); 2.5093 (3.69) 2.5049 (4.78); 2.5006 (3.64); 2.2571 (16.00); 1.6572 (0.33); 1.6395 (0.82)

17-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H 1.6275 (0.83); 1.6191 (0.96); 1.6117 (0.84); 1.5990 (0.79); -0.0002 (0.77)

[DMSO], Spektrometer: 399.95MHz

8.1790 (2.75); 8.1651 (5.42); 8.151 1 (2.80); 7.91 10 (15.55); 7.9058 (16.00); 7.5056 (1 1.96); 7.4992 (12.95); 7.4642 (1 1.69); 7.4428 (15.63); 7.3259 (8.07); 7.3194 (7.73); 7.3045 (6.07); 7.2980 (5.83); 6.8747 (15.71); 6.8695 (15.98); 3.3409 (54.02); 3.2545 (3.74); 3.2375 (9.03); 3.2220 (9.06); 3.2051 (3.98); 2.7480 (7.09); 2.7293 (9.79); 2.7096 (7.77); 2.6778 (0.48); 2.6734 (0.61); 2.6691 (0.46); 2.5438 (60.65); 2.5264 (1.86); 2.5087 (62.90); 2.5043 (83.39); 2.4998 (63.85); 2.3354 (0.40); 2.3311 (0.54); 2.3267 (0.41); 1.8158 (1.98); 1.7974 (5.61); 1.7788 (7.53); 1.7601 (5.39); 1.7422 (1.81); 0.0080

17-56 2,5-dichlor-phenyl CH2 CH2 CH2 H (0.47); -0.0002 (13.70); -0.0083 (0.63)

[DMSO], Spektrometer: 399.95MHz

8.1129 (0.67); 8.0991 (1.30); 8.0853 (0.68); 7.9061 (3.64); 7.9010 (3.71) 7.1187 (3.51); 7.0973 (4.07); 6.8816 (3.64); 6.8764 (3.67); 6.8325 (0.54) 6.8255 (4.39); 6.8041 (3.88); 4.5717 (0.50); 4.5566 (1.28); 4.5415 (1.73) 4.5265 (1.30); 4.51 14 (0.52); 3.3459 (5.03); 3.21 19 (0.89); 3.1949 (1.96) 3.1790 (1.96); 3.1622 (0.95); 2.5618 (1.61); 2.5448 (1 1.46); 2.5237 (1.88)

17-57 4-i-propoxy-phenyl CH2 CH2 CH2 H 2.5143 (2.54); 2.5100 (4.88); 2.5056 (6.48); 2.501 1 (4.98); 1.7872 (0.47)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

1.7683 (1.36); 1.7501 (1.85); 1.7317 (1.29); 1.7135 (0.43); 1.2464 (16.00); 1.2313 (16.00); -0.0002 (1.10)

[DMSO], Spektrometer: 399.95MHz

7.9177 (9.64); 7.9126 (10.03); 7.9032 (3.64); 7.8824 (3.43); 7.6218 (0.39); 7.5774 (6.16); 7.5595 (1.29); 7.5335 (12.02); 7.5299 (12.17); 7.5189 (2.87); 7.5029 (0.62); 7.4926 (0.64); 7.4584 (0.35); 6.9287 (9.37); 6.9235 (9.60); 6.9149 (0.77); 3.9956 (0.63); 3.9755 (1.44); 3.9600 (1.90); 3.9443 (1.49); 3.9240 (0.69); 3.3534 (16.27); 2.7807 (0.46); 2.7649 (0.63); 2.7569 (0.64); 2.7461 (1.87); 2.7292 (3.15); 2.7228 (2.93); 2.7064 (3.72); 2.6879 (2.03); 2.6768 (0.69); 2.6712 (0.71); 2.6534 (0.48); 2.5487 (28.87); 2.5319 (0.45); 2.5138 (13.94); 2.5094 (18.54); 2.5050 (14.40); 1.8741 (0.36); 1.8583 (0.50); 1.8515 (0.72); 1.8399 (1.22); 1.8250 (1.32); 1.8178 (1.92); 1.8030

3 -trifluormethyl- (2.44); 1.7972 (1.75); 1.7867 (1.97); 1.7799 (1.97); 1.7718 (1.81); 1.7647

(1.72); 1.7483 (1.35); 1.7389 (0.59); 1.7307 (0.61); 1.7150 (0.34); 1.1817

17-58 phenyl CH2 CH2 CH(CH3) H (0.51); 1.1608 (16.00); 1.1442 (15.88); -0.0002 (2.85)

[DMSO], Spektrometer: 399.95MHz

7.9137 (9.40); 7.9086 (9.59); 7.8870 (3.27); 7.8662 (3.28); 7.2596 (4.34); 7.2452 (5.33); 7.2381 (6.47); 7.2292 (2.57); 7.2239 (5.66); 7.1 180 (0.82); 7.1106 (6.27); 7.1055 (2.21); 7.0940 (2.46); 7.0882 (9.93); 7.0828 (2.71); 7.071 1 (1.87); 7.0661 (4.85); 7.0587 (0.64); 6.9256 (9.30); 6.9204 (9.37); 3.9715 (0.65); 3.9514 (1.44); 3.9358 (1.92); 3.9201 (1.50); 3.8999 (0.69); 3.3558 (9.54); 2.6623 (0.36); 2.6466 (0.55); 2.6388 (0.50); 2.6275 (1.88); 2.6124 (3.53); 2.6047 (2.75); 2.5894 (3.81); 2.5731 (2.03); 2.5467 (26.29); 2.5299 (0.51); 2.5158 (6.09); 2.51 18 (12.17); 2.5074 (16.17); 2.5029 (12.44); 1.8366 (0.46); 1.8202 (0.60); 1.8146 (0.91); 1.8025 (1.23); 1.7932 (0.90); 1.7872 (1.25); 1.7806 (1.89); 1.7655 (1.57); 1.7596 (1.36); 1.7448 (1.37); 1.7303 (1.60); 1.7229 (1.16); 1.7154 (1.59); 1.7085 (1.57); 1.6918 (1.34); 1.6819 (0.66); 1.6753 (0.67); 1.6586 (0.41); 1.1462 (16.00); 1.1297

17-59 4-methyl-phenyl CH2 CH2 CH(CH3) H (15.96); -0.0002 (2.69)

17-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

[DMSO], Spektrometer: 399.95MHz

7.9133 (9.29); 7.9082 (9.50); 7.8746 (3.42); 7.8538 (3.49); 7.5303 (7.20); 7.5201 (0.45); 7.5097 (8.46); 7.5008 (7.28); 7.4960 (7.56); 7.2337 (4.03); 7.2288 (4.02); 7.2130 (3.57); 7.2081 (3.56); 6.91 1 1 (9.56); 6.9059 (9.71); 3.9618 (0.63); 3.9415 (1.40); 3.9263 (1.87); 3.9105 (1.49); 3.8901 (0.69); 3.3482 (20.76); 2.681 1 (0.43); 2.6647 (0.54); 2.6584 (0.49); 2.6461 (1.92); 2.6315 (3.40); 2.6236 (2.86); 2.6145 (3.20); 2.6094 (3.54); 2.5934 (2.08); 2.5770 (0.63); 2.5581 (0.54); 2.5473 (16.67); 2.5305 (0.46); 2.5165 (7.65); 2.5125 (15.43); 2.5080 (20.67); 2.5036 (15.94); 1.8368 (0.35); 1.8201 (0.49); 1.8153 (0.74); 1.8027 (1.20); 1.7942 (0.77); 1.7814 (2.15); 1.7658 (2.21); 1.7605 (1.96); 1.7530 (1.90); 1.7452 (1.81); 1.7379 (1.92); 1.7333 (1.73); 1.7157 (1.34); 1.7046 (0.52); 1.6990 (0.52); 1.1441 (15.89); 1.1276

17-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H (16.00); -0.0002 (2.67)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz

8.1253 (1.68); 8.1 1 16 (3.23); 8.0981 (1.69); 7.91 17 (9.06); 7.9066 (9.20) 7.4187 (3.58); 7.4142 (7.05); 7.4095 (4.40); 7.3363 (16.00); 7.3317 (14.77) 6.8716 (9.31); 6.8664 (9.38); 3.3428 (25.62); 3.2070 (2.32); 3.1901 (5.61) 3.1749 (5.61); 3.1581 (2.46); 2.6645 (4.20); 2.6458 (6.99); 2.6266 (4.51) 2.5445 (29.25); 2.5275 (0.91); 2.5096 (28.36); 2.5052 (37.26); 2.5007 (28.41); 1.8263 (1.22); 1.8081 (3.76); 1.7896 (5.10); 1.7714 (3.60); 1.7535

17-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H (1.1 1); -0.0002 (5.72)

[DMSO], Spektrometer: 399.95MHz

7.9458 (1.00); 7.9201 (3.12); 7.9149 (2.95); 6.9495 (8.61); 6.9341 (2.86) 6.9289 (2.85); 4.0731 (0.46); 4.0552 (0.57); 4.0370 (0.46); 3.3484 (3.90) 2.5991 (0.60); 2.5875 (0.80); 2.5765 (0.82); 2.5684 (0.82); 2.5582 (0.92) 2.5443 (12.30); 2.5095 (3.78); 2.5050 (4.97); 2.5006 (3.79); 2.2564 (16.00) 1.5993 (0.59); 1.5780 (1.35); 1.5604 (1.10); 1.5426 (0.44); 1.5389 (0.43)

17-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H 1.2042 (4.47); 1.1875 (4.46); -0.0002 (0.86)

[DMSO], Spektrometer: 399.95MHz

7.9159 (9.37); 7.9108 (1 1.30); 7.8886 (3.51); 7.6422 (7.44); 7.6220 (9.02) 7.4590 (8.52); 7.4389 (7.15); 6.9214 (8.61); 6.9162 (8.74); 3.9910 (0.66) 3.9710 (1.47); 3.9556 (1.95); 3.9398 (1.54); 3.9196 (0.71); 3.3562 (15.85) 2.7561 (0.50); 2.7376 (1.86); 2.7235 (3.17); 2.7150 (2.91); 2.7024 (3.32) 2.6863 (2.01); 2.6701 (0.60); 2.6515 (0.35); 2.5494 (19.48); 2.5327 (0.40) 2.5145 (1 1.93); 2.5101 (15.65); 2.5058 (12.13); 1.8834 (0.42); 1.8616 (0.90); 1.8492 (1.22); 1.8464 (1.20); 1.8404 (0.92); 1.8277 (2.04); 1.81 17

4-trifluormethyl- (1.77); 1.8062 (1.76); 1.7887 (2.02); 1.7792 (1.30); 1.7709 (1.71); 1.765C

(1.66); 1.7481 (1.40); 1.7375 (0.64); 1.7317 (0.64); 1.7146 (0.38); 1.1605

17-64 phenyl CH2 CH2 CH(CH3) H (16.00); 1.1440 (15.96); -0.0002 (2.35)

[DMSO], Spektrometer: 399.95MHz

7.9161 (12.47); 7.9109 (10.86); 7.8956 (3.51); 7.4585 (7.10); 7.4509 (10.82); 7.4285 (9.20); 7.31 11 (4.80); 7.3046 (4.53); 7.2897 (3.59); 7.2833

(3.42) ; 6.9247 (9.47); 6.9195 (9.66); 4.0229 (0.74); 4.0060 (1.67); 3.9863 (2.07); 3.9691 (1.75); 3.9521 (0.79); 3.3489 (14.21); 2.7499 (0.38); 2.7350 (2.34); 2.7299 (2.64); 2.7175 (4.40); 2.7076 (4.32); 2.6956 (2.73); 2.6902 (2.62); 2.6758 (0.52); 2.5475 (26.27); 2.5306 (0.47); 2.5259 (0.62); 2.5170

(7.43) ; 2.5127 (15.17); 2.5082 (20.37); 2.5037 (15.67); 2.4997 (8.27); 1.7760 (2.20); 1.7587 (4.45); 1.7371 (4.35); 1.7190 (2.12); 1.1764 (16.00);

17-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H 1.1598 (15.96); -0.0002 (3.49)

[DMSO], Spektrometer: 399.95MHz

8.1416 (2.26); 8.1278 (4.38); 8.1 140 (2.25); 7.91 19 (12.71); 7.9067 (12.91) 7.4000 (1.05); 7.3943 (7.31); 7.3891 (2.86); 7.3816 (1.62); 7.3757 (1 1.30) 7.3730 (10.98); 7.3592 (3.48); 7.3543 (9.31); 7.3483 (1.35); 7.2570 (12.44) 7.2357 (14.15); 7.1346 (2.60); 7.1323 (4.38); 7.1299 (2.80); 7.1139 (7.39) 7.0978 (2.03); 7.0954 (3.31); 7.0930 (2.02); 6.9878 (10.15); 6.9852 (12.61) 6.9660 (1 1.14); 6.9637 (9.80); 6.9565 (2.71); 6.9486 (16.00); 6.9438 (5.72)

17-66 4-phenoxy-phenyl CH2 CH2 CH2 H 6.9321 (4.90); 6.9273 (14.23); 6.9203 (1.89); 6.8901 (12.33); 6.8849

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(12.57); 3.3529 (18.81); 3.2413 (3.04); 3.2243 (6.83); 3.2088 (6.79); 3.1918 (3.21); 2.6380 (5.28); 2.6192 (8.32); 2.5998 (5.76); 2.5459 (37.02); 2.5293 (0.53); 2.5242 (0.73); 2.5154 (8.42); 2.51 1 1 (17.04); 2.5066 (22.70); 2.5021 (17.21); 2.4980 (8.84); 1.8327 (1.62); 1.8139 (4.61); 1.7956 (6.24); 1.7771 (4.38); 1.7590 (1.46); -0.0002 (4.51)

[DMSO], Spektrometer: 399.95MHz

7.9148 (9.31); 7.9097 (9.61); 7.8856 (3.41); 7.8649 (3.46); 7.3233 (2.54) 7.3038 (6.89); 7.2938 (7.18); 7.2894 (5.52); 7.2850 (6.59); 7.2426 (4.38) 7.2386 (3.61); 7.2255 (2.04); 7.2210 (2.42); 7.1934 (4.78); 7.1746 (3.43) 6.9228 (9.33); 6.9176 (9.55); 3.9731 (0.65); 3.9530 (1.45); 3.9373 (1.94) 3.9216 (1.51); 3.9015 (0.69); 3.3503 (14.85); 2.6819 (0.44); 2.6665 (0.63) 2.6588 (0.55); 2.6477 (1.94); 2.6320 (3.64); 2.6247 (2.88); 2.6090 (4.03) 2.5920 (2.07); 2.5749 (0.70); 2.5570 (0.74); 2.5461 (26.91); 2.5290 (0.48) 2.5109 (14.21); 2.5066 (18.95); 2.5022 (14.74); 2.0803 (0.33); 1.8429 (0.40); 1.8267 (0.54); 1.8209 (0.80); 1.8088 (1.23); 1.7993 (0.85); 1.7934 (1.30); 1.7871 (2.01); 1.7690 (2.21); 1.751 1 (2.30); 1.7368 (1.72); 1.7301 (1.65); 1.7135 (1.33); 1.7036 (0.57); 1.6963 (0.60); 1.6803 (0.35); 1.1483

17-67 3-chlor-phenyl CH2 CH2 CH(CH3) H (16.00); 1.1318 (15.96); -0.0002 (3.04)

17-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

[DMSO], Spektrometer: 399.95MHz

7.9226 (3.71); 7.9138 (9.65); 7.9087 (9.95); 7.9019 (3.90); 7.5560 (6.70) 7.5513 (6.84); 7.3970 (2.67); 7.3764 (10.70); 7.3663 (7.40); 7.3615 (6.72) 7.3456 (1.65); 7.3408 (1.81); 6.9205 (9.31); 6.9153 (9.31); 4.01 18 (0.73) 3.9948 (1.57); 3.9759 (2.10); 3.9585 (1.67); 3.9409 (0.76); 3.3505 (15.85) 2.7400 (0.47); 2.7269 (2.46); 2.7221 (2.75); 2.7098 (4.10); 2.7004 (4.42) 2.6875 (2.87); 2.6824 (2.74); 2.5472 (24.81); 2.5300 (0.52); 2.5122 (16.58) 2.5078 (21.72); 2.5034 (16.52); 2.0817 (0.33); 1.7801 (0.37); 1.7676 (1.32) 1.7600 (1.59); 1.7492 (3.26); 1.7375 (2.74); 1.7297 (3.24); 1.7219 (2.83) 1.7095 (1.62); 1.7046 (1.45); 1.6927 (0.33); 1.1715 (16.00); 1.1549 (15.92)

17-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H -0.0002 (3.53)

[DMSO], Spektrometer: 399.95MHz

7.9109 (10.54); 7.9057 (12.57); 7.8833 (3.48); 7.3646 (4.15); 7.3332 (3.10) 7.3294 (3.60); 7.3146 (3.94); 7.3106 (4.51); 7.2863 (1.47); 7.2820 (1.50) 7.2671 (3.68); 7.2629 (3.45); 7.2476 (3.22); 7.2433 (2.79); 7.1958 (3.12) 7.1931 (3.69); 7.1785 (1 1.34); 7.1749 (5.90); 7.1523 (5.24); 7.1317 (3.64) 6.9929 (4.28); 6.9275 (9.62); 6.9223 (9.76); 3.9923 (0.70); 3.9737 (1.52) 3.9567 (2.1 1); 3.9398 (1.60); 3.921 1 (0.73); 3.3517 (14.29); 2.6712 (0.41) 2.6546 (3.38); 2.6344 (6.18); 2.6151 (3.77); 2.5987 (0.37); 2.5454 (33.18) 2.5285 (0.38); 2.5239 (0.48); 2.5149 (5.61); 2.5106 (11.41); 2.5061 (15.28)

2-difluormethoxy- 2.5017 (1 1.65); 1.7864 (0.74); 1.7726 (1.18); 1.7674 (1.04); 1.7521 (3.00)

1.7331 (3.96); 1.7150 (2.78); 1.6950 (1.44); 1.6822 (0.50); 1.1649 (16.00)

17-70 phenyl CH2 CH2 CH(CH3) H 1.1483 (15.94); -0.0002 (2.99)

[DMSO], Spektrometer: 399.95MHz

17-71 4-methoxy-phenyl CH2 CH2 CH2 H 8.1154 (0.58); 8.1017 (1.12); 8.0879 (0.59); 7.9071 (3.45); 7.9019 (3.52);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

7.1541 (0.38); 7.1470 (3.26); 7.1255 (3.78); 6.8825 (3.56); 6.8773 (3.59) 6.8643 (0.54); 6.8569 (4.21); 6.8520 (1.51); 6.8402 (1.29); 6.8354 (3.69) 6.8281 (0.48); 3.7181 (16.00); 3.3485 (4.93); 3.3464 (4.93); 3.2082 (0.83) 3.191 1 (1.79); 3.1755 (1.78); 3.1585 (0.88); 2.5734 (1.51); 2.5546 (2.49) 2.5443 (10.09); 2.5355 (1.82); 2.5137 (2.55); 2.5095 (5.10); 2.5050 (6.78) 2.5005 (5.18); 2.4964 (2.71); 1.7871 (0.45); 1.7681 (1.27); 1.7499 (1.73) 1.7315 (1.19); 1.7133 (0.40); -0.0002 (1.21)

[DMSO], Spektrometer: 399.95MHz

7.9102 (9.37); 7.9051 (9.64); 7.8835 (3.31); 7.8627 (3.32); 7.3334 (8.44) 7.3291 (3.40); 7.3172 (3.89); 7.3124 (14.01); 7.2482 (12.42); 7.2272 (7.78) 6.9151 (9.38); 6.9099 (9.55); 3.9599 (0.62); 3.9398 (1.38); 3.9239 (1.85) 3.9085 (1.44); 3.8883 (0.66); 3.3429 (33.50); 3.3398 (28.83); 2.6732 (0.32) 2.6623 (0.40); 2.6464 (0.52); 2.6390 (0.46); 2.6272 (1.90); 2.6126 (3.44) 2.6044 (2.81); 2.5960 (3.05); 2.5900 (3.56); 2.5742 (2.06); 2.5569 (0.68) 2.5433 (4.69); 2.5263 (0.94); 2.5085 (32.46); 2.5040 (43.18); 2.4996 (33.25); 1.8325 (0.42); 1.8106 (0.87); 1.7981 (1.16); 1.7895 (0.86); 1.7826 (1.23); 1.7766 (1.89); 1.7611 (1.58); 1.7557 (1.39); 1.7469 (1.1 1); 1.7394 (1.10); 1.7306 (1.61); 1.7235 (1.14); 1.7152 (1.56); 1.7088 (1.53); 1.6922 (1.30); 1.6820 (0.60); 1.6747 (0.62); 1.6586 (0.36); 1.1407 (16.00); 1.1242

17-72 4-chlor-phenyl CH2 CH2 CH(CH3) H (15.98); -0.0002 (6.79); -0.0080 (0.33)

[DMSO], Spektrometer: 399.95MHz

7.9210 (6.88); 7.9158 (6.99); 7.7394 (2.51); 7.7167 (2.55); 7.3268 (6.28) 7.3222 (2.46); 7.3103 (3.03); 7.3057 (10.26); 7.2427 (9.13); 7.2216 (5.74) 6.9487 (6.87); 6.9435 (6.92); 3.7815 (0.43); 3.7716 (0.56); 3.7670 (0.62) 3.7573 (1.28); 3.7440 (1.27); 3.7340 (1.27); 3.7246 (0.63); 3.7197 (0.65) 3.7141 (0.46); 3.7101 (0.47); 3.3484 (1 1.94); 2.6643 (0.55); 2.6508 (0.72) 2.6401 (0.70); 2.6288 (1.30); 2.6164 (1.12); 2.6064 (1.04); 2.5928 (0.93) 2.5468 (12.85); 2.5308 (1.09); 2.5257 (0.72); 2.5120 (10.55); 2.5075 (13.85); 2.5031 (10.20); 2.4988 (5.64); 2.4800 (0.82); 2.4733 (0.88); 2.4559 (0.61); 1.7941 (0.58); 1.7889 (0.52); 1.7768 (1.47); 1.7727 (1.39); 1.7607 (2.36); 1.7553 (1.81); 1.7452 (3.03); 1.7275 (2.17); 1.7249 (2.15); 1.7103 (1.66); 1.6990 (0.89); 1.6861 (0.78); 1.6760 (0.45); 0.8728 (16.00); 0.8557

17-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H (15.46); -0.0002 (2.35)

[DMSO], Spektrometer: 399.95MHz

8.1333 (2.48); 8.1 196 (4.75); 8.1058 (2.53); 7.9105 (15.1 1); 7.9053 (15.43) 7.2880 (0.80); 7.2806 (6.94); 7.2755 (3.27); 7.2663 (8.40); 7.2591 (10.04) 7.2503 (3.89); 7.2449 (8.86); 7.2380 (1.36); 7.1319 (1.17); 7.1243 (10.12) 7.1191 (3.30); 7.1079 (3.67); 7.1020 (16.00); 7.0962 (4.07); 7.0849 (2.87) 7.0798 (7.78); 7.0723 (1.00); 6.8921 (0.37); 6.8819 (15.19); 6.8767 (15.35) 3.3496 (21.88); 3.2187 (3.76); 3.2016 (8.28); 3.1864 (8.41); 3.1691 (4.01) 2.6336 (6.42); 2.6147 (10.23); 2.5953 (7.03); 2.5461 (45.68); 2.5292 (0.68) 2.5155 (10.63); 2.5112 (21.36); 2.5068 (28.40); 2.5023 (21.58); 2.4983 (1 1.28); 2.0803 (0.35); 1.8108 (2.05); 1.7920 (5.74); 1.7736 (7.78); 1.7551

17-74 4-fluor-phenyl CH2 CH2 CH2 H (5.47); 1.7370 (1.86); -0.0002 (4.63)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz

7.9144 (8.00); 7.9092 (8.05); 7.7826 (3.02); 7.7605 (3.08); 7.3256 (7.35) 7.321 1 (2.86); 7.3092 (3.60); 7.3045 (12.10); 7.2426 (10.83); 7.2215 (6.74) 6.9230 (8.00); 6.9178 (8.02); 3.9277 (0.83); 3.9094 (1.48); 3.8925 (1.44) 3.8735 (0.83); 3.3498 (1 1.45); 2.6567 (0.45); 2.6392 (0.76); 2.6217 (1.49) 2.6033 (2.26); 2.5885 (1.77); 2.5846 (1.81); 2.5684 (2.50); 2.5468 (1 1.14) 2.5330 (1.00); 2.5252 (0.62); 2.5161 (6.07); 2.5120 (11.61); 2.5075 (15.13) 2.5031 (1 1.40); 1.7562 (1.82); 1.7366 (3.72); 1.7176 (2.97); 1.7027 (1.20) 1.6966 (1.07); 1.4837 (1.46); 1.4643 (4.13); 1.4466 (4.92); 1.4289 (2.37) 1.3625 (0.35); 1.3452 (0.66); 1.3292 (1.47); 1.31 12 (2.42); 1.2927 (2.57) 1.2899 (2.50); 1.2708 (2.00); 1.2528 (1.08); 1.2366 (0.62); 0.8749 (8.05)

17-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H 0.8567 (16.00); 0.8384 (6.91); -0.0002 (2.85)

[DMSO], Spektrometer: 399.95MHz

7.9228 (2.58); 7.9177 (2.61); 7.6241 (0.93); 7.6000 (0.94); 7.3261 (2.22) 7.3216 (0.86); 7.3050 (3.70); 7.2455 (3.30); 7.2244 (2.03); 6.9470 (2.57) 6.9419 (2.58); 3.7681 (0.35); 3.7642 (0.37); 3.7400 (0.76); 3.7159 (0.38) 3.71 13 (0.34); 3.3497 (4.20); 2.6099 (0.50); 2.5990 (0.37); 2.5868 (0.36) 2.5467 (4.96); 2.51 19 (3.53); 2.5074 (4.65); 2.5030 (3.51); 2.4388 (0.40) 2.4345 (0.43); 2.4164 (0.38); 1.7974 (0.33); 1.7918 (0.41); 1.6760 (0.35)

17-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H 0.8714 (16.00); -0.0002 (0.79)

[DMSO], Spektrometer: 399.95MHz

8.1852 (2.64); 8.1712 (5.09); 8.1573 (2.64); 7.91 17 (15.90); 7.9065 (16.00) 7.4255 (6.16); 7.4221 (6.15); 7.4062 (7.97); 7.4027 (7.94); 7.3933 (5.09) 7.3889 (5.58); 7.3746 (6.93); 7.3703 (7.57); 7.3057 (3.1 1); 7.3022 (3.47) 7.2873 (7.71); 7.2837 (7.22); 7.2689 (5.15); 7.2651 (4.34); 7.2559 (5.61) 7.2510 (5.68); 7.2368 (6.20); 7.2322 (6.12); 7.2180 (2.41); 7.2136 (2.18) 6.8936 (0.38); 6.8836 (15.85); 6.8784 (15.89); 3.3493 (25.35); 3.265C (3.86); 3.2478 (8.57); 3.2323 (8.54); 3.2152 (4.03); 2.7566 (7.33); 2.7379 (9.57); 2.7179 (8.01); 2.5463 (46.61); 2.5295 (0.65); 2.5157 (1 1.43); 2.51 15 (22.76); 2.5070 (30.08); 2.5025 (22.68); 1.8236 (2.10); 1.8047 (5.55)

17-77 2-chlor-phenyl CH2 CH2 CH2 H 1.7863 (7.53); 1.7676 (5.20); 1.7493 (1.87); -0.0002 (5.43)

17-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

[DMSO], Spektrometer: 399.95MHz

7.9328 (3.45); 7.9150 (1 1.67); 7.9099 (12.20); 7.5802 (4.63); 7.5786 (4.57) 7.5605 (5.06); 7.5585 (4.91); 7.3661 (1.84); 7.3613 (2.38); 7.3471 (5.66) 7.3422 (5.54); 7.3332 (3.78); 7.3308 (3.66); 7.3153 (4.51); 7.3131 (4.49) 7.2966 (1.75); 7.2940 (1.68); 7.1626 (2.45); 7.1576 (2.50); 7.1427 (3.33) 7.1396 (3.31); 7.1250 (1.93); 7.1201 (1.83); 6.9353 (9.53); 6.9301 (9.50) 4.0370 (0.76); 4.0202 (1.71); 4.0006 (2.07); 3.9833 (1.77); 3.9662 (0.79) 3.3495 (13.99); 2.7573 (0.38); 2.7434 (2.39); 2.7378 (2.66); 2.7257 (4.41) 2.7154 (4.49); 2.7035 (2.77); 2.6978 (2.61); 2.6827 (0.46); 2.5467 (22.88) 2.5296 (0.35); 2.5160 (6.46); 2.51 19 (12.88); 2.5074 (17.03); 2.5029 (12.89); 1.7731 (2.25); 1.7559 (4.51); 1.7505 (3.17); 1.7337 (4.25); 1.715S

17-79 2-brom-phenyl CH2 CH2 CH(CH3) H (2.15); 1.1849 (16.00); 1.1683 (15.89); -0.0002 (3.03)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz

8.1153 (0.66); 8.1015 (1.31); 8.0877 (0.68); 7.9095 (3.89); 7.9043 (3.99); 6.8878 (3.91 ): 6.8826 (3.95); 6.8581 (2.42); 6.8377 (3.28); 6.8180 (2.67); 6.8134 (3.01 ): 6.7371 (1.69); 6.7325 (1.60); 6.7168 (i .25); 6.7121 (1.20); 3.7419 (15.94); 3.7117 (16.00); 3.3469 (7.03); 3.221 1 (0.87); 3.2040 (1.97); 3.1883 (1.97); 3.1715 (0.93); 2.5721 (1.57); 2.5532 (2.64); 2.5442 (10.06); 2.5342 (1.87); 2.5230 (0.36); 2.5136 (2.95); 2.5093 (5.98); 2.5048 (8.02);

3,4-bismethoxy- 2.5004 (6.16); 2.4963 (3.25); 1.8073 (0.46); 1.7885 (1.35); 1.7703 (1.84);

17-80 phenyl CH2 CH2 CH2 H 1.7519 (1.27); 1.7338 (0.41); -0.0002 (1.30)

Verbindung Nr. 17-81 , Solvent: [DMSO], Spektrometer: 399.95MHz 7,91 1 1 (3,22); 7,906 (3,26); 7,8715 (1 ,27); 7,8508 (1 ,28); 7,1285 (3,39); 7,1071 (3,93); 6,9286 (3,26); 6,9235 (3,27); 6,8512 (0,55); 6,8442 (4,26); 6,8227 (3,73); 3,9429 (0,56); 3,9271 (0,76); 3,91 1 1 (0,58); 3,8908 (0,36); 3,7132 (16); 3,3486 (4,51 ); 2,5671 (0,78); 2,545 (9,89); 2,531 (1 ,41 ); 2,51 (4,9); 2,5056 (6,27); 2,5012 (4,9); 1 ,7975 (0,37); 1 ,7827 (0,47); 1 ,7767 (0,37); 1 ,7635 (0,7); 1 ,748 (0,58); 1 ,743 (0,5); 1 ,7264 (0,33); 1 ,7189 (0,35); 1 ,7025 (0,59); 1 ,6953 (0,42); 1 ,687 (0,61 ); 1 ,6805 (0,6); 1 ,664 (0,52); 1 , 1391 (5,97); 1 ,1226 (5,94); -0,0002 (0,97)

17-81 4-methoxy-phenyl CH2 CH2 CH(CH3) H

Verbindung Nr. 17-82, Solvent: [DMSO], Spektrometer: 399.95MHz 7,9051 (3,98); 7,8564 (3,87); 7,367 (2,33); 7,3568 (3,14); 7,3412 (3,18); 7,3294 (2,53); 6,9643 (7,41 ); 6,9431 (3,26); 6,9317 (2,05); 6,786 (3,02); 6,5777 (4,12); 6,2593 (3,96); 3,6581 (2,6); 3,64 (4,75); 3,6216 (3,24); 3,4874 (2,55); 3,4701 (4,58); 3,4522 (2,77); 3,3222 (32,1 ); 3,1073 (2,88); 3,089 (4,93); 3,0707 (3,5); 3,0489 (3,48); 3,031 1 (4,81 ); 3,0136 (2,48); 2,9694 (15,44); 2,8893 (16); 2,675 (0,7); 2,6705 (0,96); 2,666 (0,7); 2,5403 (0,64); 2,5237 (3,17); 2,5103 (52,17); 2,5059 (102,88); 2,5014 (135,96); 2,4968 (100,49); 2,4925 (49,43); 2,3325 (0,66); 2,3282 (0,92); 2,3237 (0,67); 1 ,3357 (0,6); 1 ,2585 (0,34); 1 ,2494 (0,77); 1 ,235 (0,58); 0,008 (0,32); -0,0002

17-82 2-thienyl CH2 CH2 CH3 (8,75)

Verbindung Nr. 17-83, Solvent: [DMSO], Spektrometer: 399.95MHz 8,2417 (0,6); 8,2275 (1 ,19); 8,2131 (0,61 ); 7,8976 (3,22); 7,8924 (3,36); 7,4559 (3, 18); 7,4517 (1 ,33); 7,4395 (1 ,41 ); 7,4349 (4,93); 7,3531 (4,57); 7,332 (3,12); 6,8935 (3,26); 6,8883 (3,34); 4,3888 (0,87); 4,3749 (1 ,08); 4,371 (1 ,3); 4,3574 (0,92); 3,381 1 (0,96); 3,3671 (1 ,72); 3,3579 (1 ,33); 3,3536 (1 ,62); 3,3399 (1 ,04); 3,3228 (7,27); 3,1652 (16); 2,5247 (0,5); 2,51 12 (8,17); 2,5069 (16,23);

17-83 4-chlor-phenyl CH(OCH3) CH3 H 2,5024 (21 ,68); 2,4979 (16,58); 2,4937 (8,63); -0,0002 (1 ,22)

Verbindung Nr. 17-84, Solvent: [DMSO], Spektrometer: 601.6MHz 8,2799 (1 ,85); 8,2706 (3,61 ); 8,2612 (1 ,84); 7,9098 (15,38); 7,9064

17-84 4-chlor-2-thienyl CH2 CH2 H (16); 7,3715 (14,22); 7,3689 (14,34); 6,91 18 (9,2); 6,9106 (8,17);

7- 5 -c or-p eny N H H H H (27,16); 0,0072 (0,37); -0,0002 (5,12)

Tabelle 18

Verbindungen der Formel 1-18

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

18-1 3 -methyl-2-thienyl CH2 CH2 - H

18-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz 8.3383 (1.45); 8.3244 (2.76); 8.3106 (1.46); 7.3729 (1.04); 7.3667 (9.60); 7.3618 (3.26) 7.3506 (4.25); 7.3456 (16.00); 7.3395 (2.01); 7.2843 (2.02); 7.2785 (13.78); 7.2736 (3.81) 7.2620 (3.18); 7.2574 (8.47); 7.2512 (0.91); 3.5163 (2.66); 3.4991 (5.64); 3.4841 (5.63) 3.4661 (2.92); 3.3869 (0.37); 3.3812 (0.38); 3.3577 (1.06); 3.3334 (313.99); 2.8510 (4.86) 2.8329 (8.67); 2.8151 (4.40); 2.6761 (0.62); 2.6717 (0.87); 2.6672 (0.63); 2.5419 (8.85) 2.5250 (2.19); 2.5202 (3.29); 2.51 16 (45.83); 2.5071 (92.00); 2.5025 (121.96); 2.4979 (89.32); 2.4934 (42.57); 2.3338 (0.57); 2.3293 (0.79); 2.3247 (0.57); 0.0080 (1.38);

18-3 4-chlor-phenyl CH2 CH2 H 0.0002 (42.71); -0.0085 (1.24)

[DMSO], Spektrometer: 399.95MHz 8.4015 (1.1 1); 8.3872 (2.18); 8.3729 (1.10); 7.5903 (4.21); 7.5864 (4.70); 7.3988 (0.87); 7.3945 (0.49); 7.3781 (8.35); 7.3737 (16.00); 7.3529 (0.76); 3.5452 (2.09); 3.5281 (4.99); 3.5130 (5.12); 3.4961 (2.43); 3.3526 (1670.12); 3.2698 (0.76); 3.2279 (0.51); 3.2143 (0.33); 2.9730 (3.68); 2.9558 (7.46); 2.9384 (3.27); 2.7127 (0.59); 2.6816 (0.69); 2.6772 (1.51); 2.6725 (2.08); 2.6680 (1.47); 2.6634 (0.66); 2.5427 (177.03); 2.5260 (5.29); 2.5212 (7.81); 2.5125 (109.57); 2.5080 (223.92); 2.5034 (300.01); 2.4988 (219.02); 2.4943 (103.52); 2.3689 (0.63); 2.3393 (0.69); 2.3348 (1.46); 2.3302 (2.02); 2.3256 (1.43); 2.321 1 (0.64); 1.2346 (0.40); 0.1460 (0.56); 0.0080 (4.37); -0.0002 (149.93); -0.0085 (4.42); -

18-4 2,4-dichlor-phenyl CH2 CH2 H 0.1496 (0.58)

[DMSO], Spektrometer: 399.95MHz 8.1147 (0.61); 8.0932 (0.63); 7.9828 (0.94); 7.9620 (0.95); 7.4465 (3.15); 7.4432 (2.70) 7.4302 (1.39); 7.4254 (5.38); 7.4223 (3.60); 7.3525 (3.98); 7.3430 (2.72); 7.3369 (1.34) 7.3314 (2.64); 7.3265 (0.95); 7.3220 (1.76); 4.3564 (1.46); 4.3433 (1.68); 4.2957 (0.96) 4.2796 (1.15); 4.1896 (0.39); 4.1727 (0.55); 4.1553 (0.53); 4.1522 (0.49); 4.1383 (0.39) 4.1329 (0.38); 4.1158 (0.46); 4.1108 (0.35); 4.0990 (0.32); 4.0941 (0.44); 3.3753 (0.39) 3.3676 (0.42); 3.3334 (280.83); 3.3030 (0.41); 3.1991 (10.71); 3.1954 (16.00); 2.676C (0.43); 2.6715 (0.60); 2.6669 (0.45); 2.5418 (63.22); 2.5250 (1.48); 2.5201 (2.19); 2.51 15 (31.52); 2.5070 (64.55); 2.5024 (86.98); 2.4978 (64.44); 2.4933 (31.34); 2.3337 (0.41) 2.3292 (0.57); 2.3247 (0.42); 1.1526 (3.43); 1.1358 (3.44); 1.0899 (5.40); 1.0729 (5.38)

18-5 4-chlor-phenyl CH(OCH3) CH(CH3) H 0.0080 (0.99); -0.0002 (31.93); -0.0085 (0.99)

18-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz 8.2587 (1.23); 8.2446 (2.41); 8.2302 (1.23); 7.3788 (0.76); 7.3726 (7.48); 7.3676 (2.58) 7.3565 (3.40); 7.3513 (14.45); 7.3453 (1.89); 7.3072 (1.81); 7.3013 (12.95); 7.2962 (3.31) 7.2848 (2.49); 7.2800 (7.06); 7.2741 (0.75); 3.4313 (3.82); 3.4130 (5.92); 3.3981 (5.02) 3.3792 (0.59); 3.3746 (0.55); 3.3667 (0.81); 3.3336 (441.38); 3.3027 (0.50); 3.2970 (0.37) 3.0900 (1.20); 3.0721 (2.38); 3.0542 (2.29); 3.0361 (1.09); 2.6761 (0.72); 2.6715 (1.00) 2.6669 (0.72); 2.6623 (0.32); 2.5418 (75.45); 2.5249 (2.60); 2.5202 (3.74); 2.51 15 (52.54) 2.5070 (107.79); 2.5023 (144.94); 2.4977 (106.89); 2.4932 (51.49); 2.3337 (0.67); 2.3291 (0.97); 2.3245 (0.68); 1.2297 (16.00); 1.2121 (15.70); 0.0080 (0.90); -0.0002 (30.79); -

18-7 4-chlor-phenyl CH(CH3) CH2 H 0.0085 (0.93)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

18-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

[DMSO], Spektrometer: 399.95MHz 8.1684 (2.39); 8.1575 (0.72); 8.1476 (2.42); 7.3554 (0.73); 7.3492 (7.88); 7.3444 (2.76) 7.3331 (3.38); 7.3281 (14.10); 7.3222 (1.89); 7.2691 (1 1.74); 7.2480 (7.01); 4.1879 (0.58) 4.1676 (1.20); 4.151 1 (1.90); 4.1344 (1.38); 4.1147 (0.62); 3.4896 (0.32); 3.4577 (0.49) 3.4446 (0.45); 3.4350 (0.52); 3.4276 (0.67); 3.4152 (0.79); 3.4083 (0.83); 3.3772 (2.46) 3.3337 (2834.39); 3.2709 (1.22); 3.2358 (0.55); 3.2193 (0.38); 2.8564 (0.73); 2.8363 (0.65); 2.8224 (3.63); 2.8103 (4.00); 2.8027 (4.16); 2.7947 (4.04); 2.7766 (0.76); 2.7607 (0.57); 2.6801 (2.08); 2.6756 (4.53); 2.6710 (6.32); 2.6665 (4.61); 2.6620 (2.22); 2.602C (0.34); 2.5413 (21.69); 2.5244 (15.29); 2.5197 (23.07); 2.51 10 (323.58); 2.5065 (666.17) 2.5019 (898.26); 2.4973 (661.97); 2.4928 (317.58); 2.3378 (1.97); 2.3333 (4.37); 2.3287 (6.09); 2.3241 (4.39); 2.3197 (2.07); 2.2889 (0.47); 1.2578 (0.44); 1.2351 (0.97); 1.1864 (16.00); 1.1699 (15.83); 0.1459 (0.48); 0.0080 (3.73); -0.0002 (124.43); -0.0085 (3.51);

18-9 4-chlor-phenyl CH2 CH(CH3) H 0.1495 (0.50)

[DMSO], Spektrometer: 399.95MHz 8.3159 (0.35); 8.2349 (2.20); 8.2137 (2.22); 7.5731 (3.36); 7.5703 (6.07); 7.5674 (3.69) 7.3687 (16.00); 7.3658 (15.36); 4.3258 (0.44); 4.3042 (1.07); 4.2881 (1.34); 4.2727 (1.05) 4.2517 (0.49); 3.6123 (0.36); 3.5587 (0.37); 3.5460 (0.39); 3.5174 (0.50); 3.5025 (0.59) 3.4877 (0.58); 3.4696 (0.67); 3.4588 (1.03); 3.4418 (1.03); 3.4227 (1.45); 3.3982 (2.57) 3.3351 (5077.54); 3.2907 (3.09); 3.2810 (2.65); 3.2568 (1.10); 3.2516 (1.05); 3.2389 (0.88); 3.2218 (0.60); 3.2087 (0.53); 3.1956 (0.50); 3.1860 (0.43); 3.1793 (0.33); 3.1605 (0.48); 3.1330 (0.33); 2.9947 (0.36); 2.9852 (0.92); 2.9712 (1.12); 2.9510 (3.40); 2.934S

(4.38) ; 2.9121 (3.04); 2.8995 (0.99); 2.8901 (0.39); 2.8780 (1.04); 2.7099 (0.37); 2.6801 (3.06); 2.6757 (6.56); 2.671 1 (9.23); 2.6665 (6.68); 2.6620 (3.14); 2.6417 (0.32); 2.6214 (0.51); 2.61 19 (0.54); 2.5966 (0.60); 2.5693 (1.1 1); 2.5414 (40.35); 2.5245 (23.18); 2.5197 (33.93); 2.51 11 (471.06); 2.5066 (969.31); 2.5020 (1306.95); 2.4974 (961.78); 2.4929 (462.06); 2.4530 (1.02); 2.4186 (0.46); 2.3379 (2.88); 2.3333 (6.32); 2.3287 (8.86); 2.3241

(6.39) ; 2.3197 (2.94); 2.2893 (0.71); 1.4338 (0.33); 1.2977 (0.58); 1.2581 (0.99); 1.232C (14.66); 1.2153 (13.1 1); 1.1813 (0.35); 1.1656 (0.33); 0.8704 (0.33); 0.8537 (0.47); 0.146C

18-10 2,4-dichlor-phenyl CH2 CH(CH3) H (0.62); 0.0079 (4.21); -0.0003 (140.87); -0.0085 (4.14); -0.1497 (0.56)

[DMSO], Spektrometer: 399.95MHz 7.9826 (0.42); 7.9676 (0.84); 7.9523 (0.45); 7.4509 (2.05); 7.4343 (1.05); 7.4292 (4.00); 7.3877 (0.55); 7.3814 (4.00); 7.3647 (0.87); 7.3596 (2.18); 3.4783 (2.79); 3.4627 (2.80); 3.3817 (0.38); 3.3708 (0.61); 3.3382 (185.17); 3.2999 (0.37); 2.6718 (0.33); 2.5421 (32.30); 2.5248 (1.10); 2.5071 (35.24); 2.5027 (48.02); 2.4983 (38.24); 2.3294 (0.32);

18-11 4-chlor-phenyl C(CH3)2 CH2 H 1.3079 (16.00); -0.0002 (5.06)

[DMSO], Spektrometer: 399.95MHz 8.0483 (0.38); 8.0336 (0.76); 8.0185 (0.38); 7.5470 (2.21); 7.5412 (2.35); 7.4867 (1.60) 7.4650 (2.48); 7.3951 (1.76); 7.3893 (1.62); 7.3735 (1.15); 7.3677 (1.11); 3.8178 (2.76) 3.8020 (2.73); 3.3793 (0.46); 3.3648 (0.85); 3.3383 (270.44); 2.6763 (0.35); 2.6718 (0.49) 2.6671 (0.34); 2.5420 (36.71); 2.5251 (1.23); 2.5204 (1.98); 2.51 18 (26.71); 2.5072 (53.98); 2.5026 (71.90); 2.4980 (52.51); 2.4935 (24.80); 2.3340 (0.34); 2.3294 (0.47)

18-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 2.3248 (0.33); 1.4601 (16.00); -0.0002 (8.50)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

[DMSO], Spektrometer: 399.95MHz 8.4047 (2.52); 8.3907 (4.88); 8.3766 (2.61); 7.4404 (6.45); 7.4365 (4.88); 7.4350 (4.64) 7.4222 (9.21); 7.4173 (8.49); 7.4008 (0.37); 7.3654 (4.74); 7.3599 (6.00); 7.3468 (6.72) 7.3421 (9.18); 7.3273 (0.39); 7.3124 (3.08); 7.3081 (4.16); 7.2941 (9.79); 7.2898 (9.16) 7.2798 (9.24); 7.2770 (9.45); 7.2736 (9.93); 7.2719 (7.64); 7.261 1 (7.85); 7.2558 (6.91) 7.2427 (2.64); 7.2376 (2.13); 3.5551 (4.91); 3.5380 (10.36); 3.5229 (10.15); 3.5049 (5.55) 3.3678 (1276.41); 3.2303 (0.70); 3.1844 (0.39); 3.1732 (0.34); 3.1611 (0.34); 3.1526 (0.34); 2.9921 (9.29); 2.9740 (16.00); 2.9565 (8.30); 2.6830 (0.53); 2.6785 (1.12); 2.6739 (1.54); 2.6693 (1.1 1); 2.6647 (0.54); 2.5440 (26.94); 2.5272 (4.13); 2.5224 (6.63); 2.513S (78.38); 2.5093 (158.33); 2.5047 (210.97); 2.5001 (154.60); 2.4956 (73.64); 2.3406 (0.53) 2.3361 (1.10); 2.3315 (1.50); 2.3269 (1.07); 2.3223 (0.50); 1.2338 (0.92); 0.0080 (0.68);

18-13 2-chlor-phenyl CH2 CH2 H 0.0002 (18.93); -0.0085 (0.53)

[DMSO], Spektrometer: 399.95MHz 8.3558 (2.16); 8.3425 (4.30); 8.3280 (2.26); 8.3157 (0.59); 7.5658 (13.70); 7.5557 (0.53) 7.5452 (16.00); 7.5367 (1 1.66); 7.5317 (12.12); 7.2572 (6.90); 7.2520 (6.73); 7.2366 (6.16); 7.2315 (6.00); 3.6967 (0.33); 3.6686 (0.37); 3.6487 (0.44); 3.6021 (0.52); 3.5839 (0.53); 3.5344 (4.32); 3.5171 (10.67); 3.5024 (1 1.03); 3.4854 (5.22); 3.4631 (1.39); 3.432C (2.05); 3.4217 (2.24); 3.4018 (4.27); 3.3395 (5202.56); 3.2846 (3.40); 3.2691 (1.97) 3.2381 (0.93); 3.2298 (0.90); 3.2222 (0.97); 3.2102 (0.71); 3.1817 (0.46); 3.1514 (0.46) 3.1348 (0.38); 3.1097 (0.38); 3.0893 (0.33); 2.9294 (0.43); 2.8901 (0.40); 2.8654 (7.26) 2.8483 (14.70); 2.8310 (6.59); 2.7303 (0.44); 2.711 1 (0.53); 2.6806 (3.27); 2.6761 (6.70) 2.6715 (9.14); 2.6669 (6.77); 2.6624 (3.28); 2.5417 (67.51); 2.5249 (24.44); 2.5202 (37.04); 2.51 15 (469.46); 2.5070 (954.80); 2.5024 (1275.92); 2.4978 (935.38); 2.4932 (444.13); 2.3383 (2.78); 2.3337 (6.15); 2.3291 (8.50); 2.3245 (6.09); 2.3200 (2.74); 2.2906 (0.75); 1.4598 (0.49); 1.4341 (0.34); 1.2974 (0.53); 1.2583 (0.73); 1.2439 (0.83); 1.2344

18-14 3 ,4-dichlor-phenyl CH2 CH2 H (2.20); 0.0079 (2.35); -0.0002 (75.50); -0.0085 (2.08)

[DMSO], Spektrometer: 399.95MHz 8.3635 (1.59); 8.3495 (3.02); 8.3358 (1.55); 7.4561 (3.52); 7.4514 (6.76); 7.4467 (3.82) 7.3362 (16.00); 7.3315 (14.73); 3.5441 (2.54); 3.5273 (6.64); 3.5123 (6.80); 3.4957 (2.79) 3.4538 (0.33); 3.4358 (0.44); 3.4020 (0.84); 3.3403 (774.15); 3.3073 (1.15); 3.2955 (0.64) 2.8758 (4.51); 2.8589 (9.13); 2.8420 (4.07); 2.6766 (0.93); 2.6721 (1.22); 2.6676 (0.90) 2.5423 (1 1.07); 2.5251 (4.02); 2.51 18 (70.19); 2.5075 (133.89); 2.5030 (174.54); 2.4985 (128.16); 2.4943 (62.55); 2.3342 (0.84); 2.3297 (1.13); 2.3252 (0.81); 0.0080 (0.39);

18-15 3,5- dichlor-pheny 1 CH2 CH2 H 0.0002 (7.87)

[DMSO], Spektrometer: 399.95MHz 8.3502 (2.22); 8.3363 (4.27); 8.3224 (2.34); 7.3668 (0.45); 7.3518 (4.27); 7.3458 (0.95) 7.3317 (16.00); 7.3251 (7.19); 7.3136 (10.84); 7.2894 (5.46); 7.2862 (7.75); 7.2812 (5.74) 7.2696 (3.01); 7.2645 (3.28); 7.261 1 (2.32); 7.2249 (4.84); 7.2215 (7.70); 7.2066 (3.86) 7.2028 (5.51); 3.5338 (4.43); 3.5164 (9.92); 3.5017 (10.19); 3.4841 (5.10); 3.4659 (0.60) 3.4537 (0.48); 3.4464 (0.55); 3.4364 (0.64); 3.4250 (0.90); 3.3951 (1.97); 3.3446 (1716.20); 3.2744 (0.85); 3.2561 (0.57); 3.2491 (0.55); 3.2412 (0.52); 3.2322 (0.40) 2.8910 (0.54); 2.8694 (7.72); 2.8517 (14.91); 2.8340 (7.33); 2.8151 (0.34); 2.7318 (0.38) 2.7123 (1.48); 2.6812 (0.87); 2.6767 (1.80); 2.6721 (2.50); 2.6676 (1.79); 2.6630 (0.84) 2.5833 (0.45); 2.5767 (0.51); 2.5760 (0.51); 2.5730 (0.52); 2.5701 (0.62); 2.5694 (0.61)

18-16 3-chlor-phenyl CH2 CH2 H 2.5672 (0.69); 2.5665 (0.68); 2.5657 (0.65); 2.5627 (0.90); 2.5621 (0.94); 2.5614 (0.92)

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

2.5423 (412.00); 2.5307 (1.62); 2.5256 (6.01); 2.5208 (8.89); 2.5121 (124.91); 2.5076 (254.80); 2.5030 (340.40); 2.4984 (248.09); 2.4938 (1 17.28); 2.3685 (1.43); 2.3389 (0.77); 2.3343 (1.68); 2.3298 (2.33); 2.3252 (1.65); 2.3207 (0.73); 1.2346 (0.40); 0.0080 (0.42); - 0.0002 (13.65); -0.0086 (0.34)

[DMSO], Spektrometer: 399.95MHz 8.3957 (2.90); 8.3818 (5.52); 8.3678 (2.98); 7.3361 (3.19); 7.3319 (3.87); 7.3174 (6.62); 7.3128 (8.10); 7.3043 (2.78); 7.2978 (4.46); 7.2936 (5.27); 7.2859 (4.82); 7.2795 (3.29); 7.2712 (4.94); 7.2654 (5.84); 7.2609 (3.14); 7.2518 (3.50); 7.2472 (2.69); 7.1764 (6.27); 7.1566 (1 1.90); 7.1532 (8.27); 7.1501 (5.99); 7.1406 (1 1.91); 7.1377 (10.17); 7.1327 (4.90); 7.1298 (4.37); 7.1222 (5.1 1); 7.1192 (4.17); 3.6834 (0.33); 3.5782 (0.41); 3.5280 (6.02); 3.5109 (12.37); 3.4955 (12.32); 3.4775 (6.60); 3.4568 (1.25); 3.3476 (2316.66); 3.2151 (0.83); 2.8992 (8.80); 2.8814 (16.00); 2.8635 (7.91); 2.7319 (0.57); 2.7122 (2.12); 2.681 1 (1.30); 2.6768 (2.57); 2.6721 (3.53); 2.6676 (2.57); 2.6631 (1.29); 2.6135 (0.46); 2.6069 (0.50); 2.5790 (0.94); 2.5425 (525.77); 2.5256 (9.51); 2.5207 (14.47); 2.5121 (181.56); 2.5076 (362.66); 2.5030 (480.12); 2.4984 (349.45); 2.4939 (165.02); 2.3684 (1.93); 2.3389 (1.04); 2.3344 (2.31); 2.3298 (3.19); 2.3253 (2.24); 2.3206 (0.99); 1.2347

18-17 2-fluor-phenyl CH2 CH2 H (0.54); 0.0079 (0.34); -0.0002 (10.27)

18-18 2,6-difluor-phenyl CH2 CH2 - H

[DMSO], Spektrometer: 399.95MHz 8.4790 (1.26); 8.4644 (2.57); 8.4500 (1.31); 7.4643 (1 1.15); 7.4442 (16.00); 7.4223 (0.44); 7.4174 (0.44); 7.3413 (0.38); 7.3057 (5.89); 7.2938 (0.56); 7.2867 (5.55); 7.2844 (5.33); 7.2714 (0.55); 7.2654 (3.92); 7.2554 (0.36); 3.5541 (2.22); 3.5373 (5.65); 3.5216 (5.80); 3.5048 (2.68); 3.4705 (0.46); 3.4658 (0.45); 3.4373 (0.52); 3.4210 (0.86); 3.3411 (1529.98); 3.2968 (1.65); 3.2504 (0.51); 3.2346 (0.41); 3.2214 (0.35); 3.2060 (0.39); 3.1841 (4.37); 3.1668 (8.06); 3.1495 (3.65); 2.9916 (0.41); 2.9731 (0.67); 2.9558 (0.42); 2.6809 (0.87); 2.6764 (1.83); 2.6718 (2.53); 2.6672 (1.82); 2.6627 (0.88); 2.5420 (39.84); 2.5252 (6.83); 2.5204 (10.41); 2.51 18 (129.79); 2.5073 (262.65); 2.5027 (350.05); 2.4981 (255.24); 2.4935 (120.13); 2.3387 (0.77); 2.3341 (1.70); 2.3295 (2.34); 2.3249 (1.68);

18-19 2,6-dichlor-phenyl CH2 CH2 H 2.3204 (0.76); 1.2347 (0.43); 0.0080 (1.16); -0.0002 (36.14); -0.0085 (0.97)

[DMSO], Spektrometer: 399.95MHz 8.3596 (2.58); 8.3455 (4.62); 8.3316 (2.38); 7.6766 (0.93); 7.6566 (1.19); 7.6020 (9.79); 7.5891 (2.76); 7.5766 (5.18); 7.5715 (9.15); 7.5651 (13.92); 7.5613 (1 1.18); 7.5553 (12.55); 7.5375 (3.49); 7.5267 (0.45); 7.5194 (1.32); 7.4865 (0.98); 7.4665 (0.87); 3.5706 (4.51); 3.5532 (1 1.20); 3.5385 (1 1.39); 3.5213 (5.00); 3.4202 (0.65); 3.3409 (891.91); 2.9678 (8.02); 2.9504 (16.00); 2.9330 (7.25); 2.8913 (0.59); 2.7323 (0.48); 2.7128 (1.33); 2.6815 (0.56); 2.6771 (1.13); 2.6724 (1.56); 2.6679 (1.12); 2.6633 (0.54); 2.5841 (0.43);

3 -(trifluormethyl)- 2.5427 (366.31); 2.5258 (3.99); 2.5211 (5.99); 2.5125 (80.10); 2.5079 (162.32); 2.5033

(216.15); 2.4987 (157.36); 2.4942 (73.95); 2.3690 (1.24); 2.3392 (0.45); 2.3347 (1.01);

18-20 phenyl CH2 CH2 H 2.3301 (1.41); 2.3255 (1.00); 2.3209 (0.43); 0.0080 (1.82); -0.0002 (60.87); -0.0085 (1.71)

[DMSO], Spektrometer: 399.95MHz 8.3826 (2.67); 8.3689 (5.23); 8.3550 (2.75); 7.6766 (13.01); 7.6564 (16.00); 7.4861

4-(trifluormethyl)- (14.81); 7.4660 (12.51); 3.5654 (4.59); 3.5481 (10.38); 3.5329 (10.38); 3.5154 (5.13);

3.4825 (0.34); 3.4664 (0.51); 3.4607 (0.50); 3.4501 (0.46); 3.4333 (0.61); 3.4100 (0.95);

18-21 phenyl CH2 CH2 H 3.3992 (1.04); 3.3366 (1695.91); 3.2803 (1.01); 3.2604 (0.42); 2.9580 (7.44); 2.9402

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(13.90); 2.9225 (6.64); 2.6806 (1.15); 2.6761 (2.39); 2.6716 (3.33); 2.6671 (2.42); 2.6625

(1.16) ; 2.5419 (22.64); 2.5249 (8.60); 2.5201 (12.91); 2.51 15 (173.78); 2.5070 (351.71); 2.5025 (470.69); 2.4979 (347.82); 2.4935 (169.16); 2.3383 (1.06); 2.3338 (2.27); 2.3293

(3.17) ; 2.3247 (2.27); 2.3202 (1.04); 1.2350 (0.53); 0.1461 (0.33); 0.0080 (2.40); -0.0002 (76.44); -0.0084 (2.40)

[DMSO], Spektrometer: 399.95MHz 8.4044 (0.57); 8.3908 (1.07); 8.3760 (0.56); 7.1690 (1.37); 7.1574 (1.84); 7.1457 (3.82) 7.1393 (1.52); 7.1345 (1.20); 7.1292 (3.37); 7.1265 (3.45); 7.1190 (1.24); 7.1159 (2.25) 7.11 15 (1.16); 7.1050 (1.52); 3.4652 (1.06); 3.4501 (1.93); 3.4421 (1.18); 3.4318 (1.61) 3.4272 (2.00); 3.4125 (1.29); 3.3974 (0.44); 3.3925 (0.49); 3.3845 (0.74); 3.3364 (628.44) 3.3074 (0.93); 3.2961 (0.61); 2.8518 (2.05); 2.8364 (1.70); 2.8321 (2.36); 2.8135 (1.84) 2.6802 (0.37); 2.6759 (0.82); 2.6713 (1.14); 2.6668 (0.83); 2.6622 (0.36); 2.5416 (5.14) 2.5247 (3.20); 2.5199 (4.87); 2.51 13 (61.1 1); 2.5068 (123.14); 2.5022 (163.88); 2.4976 (120.10); 2.4931 (57.14); 2.3381 (0.45); 2.3335 (0.93); 2.3289 (1.44); 2.3194 (16.00)

18-22 2-methyl-phenyl CH2 CH2 H 0.0080 (0.89); -0.0002 (28.19); -0.0085 (0.82)

2,4,6-trimethyl-

18-23 phenyl CH2 CH2 - H

[DMSO], Spektrometer: 399.95MHz 8.2840 (0.49); 8.2698 (0.94); 8.2559 (0.48); 6.8795 (2.01); 6.8591 (2.74); 6.8349 (2.13) 6.8302 (2.31); 6.7589 (1.36); 6.7542 (1.21); 6.7386 (0.99); 6.7339 (0.88); 3.7305 (15.58) 3.7120 (16.00); 3.5042 (0.78); 3.4874 (1.53); 3.4693 (1.46); 3.4534 (0.86); 3.3957 (0.32) 3.3777 (0.64); 3.3382 (330.27); 3.2953 (0.36); 2.7870 (1.36); 2.7685 (2.24); 2.7505 (1.24) 2.6761 (0.42); 2.6714 (0.58); 2.6671 (0.42); 2.5418 (80.42); 2.5315 (0.67); 2.5249 (1.50) 2.5201 (2.29); 2.51 14 (32.05); 2.5070 (64.65); 2.5024 (85.98); 2.4978 (63.63); 2.4934

3,4-bismethoxy- (30.94); 2.3680 (0.34); 2.3336 (0.40); 2.3292 (0.57); 2.3246 (0.41); 0.0080 (0.36); -0.0002

18-24 phenyl CH2 CH2 H (12.16); -0.0085 (0.37)

[DMSO], Spektrometer: 399.95MHz 8.3334 (1.80); 8.3197 (3.63); 8.3058 (2.10); 7.3248 (4.55); 7.3210 (1.73); 7.3065 (12.05); 7.2931 (3.50); 7.2885 (12.51); 7.2563 (9.87); 7.2524 (16.00); 7.2334 (10.00); 7.2170 (2.59); 7.21 18 (6.73); 7.2062 (1.87); 7.1978 (1.62); 7.1940 (2.54); 3.7304 (0.33); 3.7120 (0.36); 3.5240 (4.33); 3.5072 (7.33); 3.4915 (7.04); 3.4878 (7.57); 3.4727 (5.04); 3.3423 (2075.15); 2.8909 (0.51); 2.8572 (7.70); 2.8382 (1 1.32); 2.8203 (6.95); 2.7306 (0.47); 2.7120 (1.54); 2.6763 (2.50); 2.6718 (3.33); 2.6671 (2.49); 2.6626 (1.25); 2.5420 (409.43); 2.5252 (8.63); 2.5204 (12.67); 2.51 18 (161.71); 2.5072 (328.42); 2.5026 (437.97); 2.4980 (318.47); 2.4935 (149.52); 2.3683 (1.16); 2.3386 (0.86); 2.3340 (2.04); 2.3294 (2.86);

18-25 phenyl CH2 CH2 H 2.3248 (2.00); 2.3203 (0.82); 1.2349 (0.53); 0.0080 (1.34); -0.0002 (37.49); -0.0085 (0.79)

C(CH2-

18-26 4-chlor-phenyl CH2) CH2 H

C(CH2-

18-27 2,4-dichlor-phenyl CH2) CH2 - H

18-28 4-chlor-phenyl CH2 C(CH2- - H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

CH2)

C(CH2-

18-29 2,4-dichlor-phenyl CH2 CH2) H

18-30 4-chlor-phenyl 0 CH2 CH2 H

18-31 2,4-dichlor-phenyl 0 CH2 CH2 H

18-32 4-chlor-phenyl CH2 CH2 CH2 H

18-33 4-chlor-phenyl NCH3 CH2 CH2 H

18-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

18-35 4-chlor-phenyl CH(OCH3) CH2 - H

18-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 18-37, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4026 (2,85); 8,3891 (5,07); 8,3758 (2,83); 7,3603 (7,73); 7,3576 (7,29); 7,3476 (8,4); 7,3448 (7,56); 6,9744 (5,8); 6,9657 (8,94); 6,962 (6,02); 6,9532 (8,02); 6,9271 (9,64); 6,9195 (6,84); 3,5416 (4,44); 3,5242 (10,59); 3,509 (1 1, 17); 3,4915 (5,08); 3,3274 (120,31); 3,0811 (8,92); 3,0632 (16); 3,0454 (7,69); 2,6712 (0,67); 2,5416 (1 ,37); 2,5062

18-37 2-thienyl CH2 CH2 H (81,74); 2,5022 (102,18); 2,4981 (77,29); 2,329 (0,7); -0,0002 (1 ,69)

18-38 3-thienyl CH2 CH2 - H

18-39 2-furyl CH2 CH2 - H

18-40 3-furyl CH2 CH2 - H

18-41 phenyl CH2 CH2 CH(CH3) H

18-42 phenyl CH2 CH2 CH2 H

18-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

18-44 4-t-butyl-phenyl CH2 CH2 CH2 H

18-45 4-methyl-phenyl CH2 CH2 CH2 H

18-46 phenyl CH2 CH2 CH(CH2CH3) H

18-47 2-methoxy-phenyl CH2 CH2 CH2 H

18-48 2-methyl-phenyl CH2 CH2 CH2 H

18-49 3 -methyl-phenyl CH2 CH2 CH2 H

18-50 3-chlor-phenyl CH2 CH2 CH2 H

18-51 2,6-difluor-phenyl CH2 CH2 CH2 H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

18-52 4-chlor-phenyl CH2 CH2 CH2 H

18-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

18-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

2,6-dimethyl-

18-55 phenyl CH2 CH2 CH2 H

18-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

18-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

3 -trifluormethyl-

18-58 phenyl CH2 CH2 CH(CH3) H

18-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

18-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

18-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

18-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

2,6-dimethyl-

18-63 phenyl CH2 CH2 CH(CH3) H

4-trifluormethyl-

18-64 phenyl CH2 CH2 CH(CH3) H

18-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

18-66 4-phenoxy-phenyl CH2 CH2 CH2 H

18-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

18-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

18-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

2-difluormethoxy-

18-70 phenyl CH2 CH2 CH(CH3) H

18-71 4-methoxy-phenyl CH2 CH2 CH2 H

18-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

18-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

18-74 4-fluor-phenyl CH2 CH2 CH2 H

18-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

18-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

18-77 2-chlor-phenyl CH2 CH2 CH2 H

18-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Tabelle 19

Verbindungen der Formel 1-19

1-19

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

19-1 3 -methyl-2-thienyl CH2 CH2 - H

19-2 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101976

[DMSO], Spektrometer: 399.95MHz 8.7804 (1.61); 8.7666 (2.98); 8.7533 (1.69); 7.3729 (9.38); 7.3684 (3.79); 7.3566 (4.52) 7.3519 (16.00); 7.3464 (2.86); 7.2909 (14.36); 7.2699 (8.86); 3.5300 (2.87); 3.5127 (6.87) 3.4975 (6.94); 3.4802 (3.25); 3.3432 (53.59); 2.8588 (5.46); 2.8410 (10.32); 2.8233 (5.05) 2.5440 (6.08); 2.5090 (29.64); 2.5046 (39.14); 2.5002 (29.94); 2.0786 (1.17); -0.0002

19-3 4-chlor-phenyl CH2 CH2 H (4.99)

[DMSO], Spektrometer: 399.95MHz 8.8319 (1.09); 8.8182 (2.04); 8.8041 (1.10); 7.6008 (3.91); 7.5980 (5.81); 7.41 14 (0.32) 7.3901 (12.93); 7.3871 (16.00); 7.3689 (0.34); 3.5560 (1.82); 3.5389 (4.91); 3.5238 (5.01) 3.5070 (2.05); 3.3452 (150.16); 2.9809 (3.79); 2.9637 (7.76); 2.9464 (3.42); 2.6728 (0.41) 2.5432 (6.83); 2.5262 (1.41); 2.5127 (23.77); 2.5083 (47.67); 2.5038 (62.98); 2.4992 (47.09); 2.4948 (23.94); 2.3306 (0.41); 2.0773 (1.79); 0.0080 (0.34); -0.0002 (10.17);

19-4 2,4-dichlor-phenyl CH2 CH2 H 0.0085 (0.44)

[DMSO], Spektrometer: 399.95MHz 8.6720 (0.83); 8.6503 (0.84); 8.5858 (1.06); 8.5647 (1.07); 7.4562 (3.64); 7.4520 (3.91) 7.4351 (6.33); 7.4309 (4.83); 7.3606 (4.59); 7.3404 (5.97); 7.3199 (2.51); 4.3370 (1.82) 4.3233 (2.21); 4.2540 (1.43); 4.2378 (1.90); 4.2202 (0.54); 4.2031 (0.72); 4.1996 (0.64) 4.1890 (0.56); 4.1854 (0.66); 4.1827 (0.62); 4.1683 (0.46); 4.1301 (0.46); 4.1135 (0.69) 4.1087 (0.53); 4.0968 (0.48); 4.0920 (0.68); 4.0754 (0.40); 3.3409 (73.80); 3.1983 (13.14) 3.1836 (16.00); 2.5431 (4.17); 2.5261 (0.83); 2.5213 (1.23); 2.5127 (14.60); 2.5083 (29.47); 2.5037 (39.10); 2.4992 (29.18); 2.4948 (14.65); 2.0775 (2.35); 1.1695 (4.92)

19-5 4-chlor-phenyl CH(0CH3) CH(CH3) H 1.1527 (4.90); 1.0737 (5.89); 1.0566 (5.86); -0.0002 (5.08)

19-6 2,4-dichlor-phenyl CH(0CH3) CH(CH3) - H

[DMSO], Spektrometer: 399.95MHz 8.7346 (1.37); 8.7208 (2.60); 8.7066 (1.41); 7.3845 (0.88); 7.3786 (7.46); 7.3738 (2.91) 7.3624 (3.84); 7.3573 (14.36); 7.3515 (2.43); 7.3103 (13.32); 7.3055 (3.96); 7.2935 (2.86) 7.2890 (7.26); 3.4569 (0.35); 3.4429 (2.88); 3.4379 (2.86); 3.4235 (6.1 1); 3.4081 (3.74) 3.4062 (3.84); 3.3906 (0.38); 3.3874 (0.38); 3.3432 (43.13); 3.0839 (1.34); 3.0661 (2.65) 3.0482 (2.58); 3.0303 (1.24); 2.5442 (5.28); 2.5273 (0.65); 2.5225 (0.99); 2.5137 (11.38) 2.5094 (22.74); 2.5048 (29.96); 2.5003 (22.48); 2.4960 (1 1.55); 2.0788 (1.96); 1.2453

19-7 4-chlor-phenyl CH(CH3) CH2 H (16.00); 1.2278 (15.80); -0.0002 (4.41)

[DMSO], Spektrometer: 399.95MHz 8.8147 (1.76); 8.8006 (3.14); 8.7893 (1.62); 7.5801 (9.54); 7.5748 (10.09); 7.4937 (5.81) 7.4726 (11.68); 7.4585 (0.32); 7.4369 (7.10); 7.4315 (6.55); 7.4159 (3.48); 7.4104 (3.35) 3.5791 (1.06); 3.5625 (2.52); 3.5467 (3.86); 3.5373 (2.96); 3.5270 (3.67); 3.5124 (3.99) 3.4968 (1.82); 3.4874 (1.70); 3.4733 (1.37); 3.4631 (2.34); 3.4491 (2.88); 3.4355 (1.44) 3.4251 (0.61); 3.4175 (0.49); 3.4109 (0.34); 3.3420 (126.95); 2.6732 (0.41); 2.5437 (7.71) 2.5266 (1.34); 2.5131 (24.03); 2.5087 (48.16); 2.5042 (63.58); 2.4996 (47.39); 2.4952

19-8 2,4-dichlor-phenyl CH(CH3) CH2 H (24.03); 2.3309 (0.42); 2.0782 (3.45); 1.2396 (15.60); 1.2233 (16.00); -0.0002 (7.21)

[DMSO], Spektrometer: 399.95MHz

19-9 4-chlor-phenyl CH2 CH(CH3) - H 8.6741 (2.64); 8.6534 (2.68); 7.3663 (0.98); 7.3604 (8.41); 7.3560 (3.27); 7.3442 (3.93);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 |ppm] oder CAS- bzw. Patent-Nr.

7.3394 (13.89); 7.3337 (2.30); 7.2747 (12.38); 7.2537 (7.77); 4.2068 (0.71); 4.1886 (1.65); 4.1712 (2.18); 4.1521 (1.64); 4.1349 (0.79); 3.3435 (51.80); 2.8243 (0.45); 2.8066 (8.20); 2.7880 (5.81); 2.7530 (0.34); 2.5442 (5.12); 2.5270 (0.63); 2.5135 (12.25); 2.5093 (24.47); 2.5048 (32.40); 2.5003 (24.57); 2.4962 (12.91 ); 2.0787 (3.43); 1.1902 (16.00); 1.1736 (15.92); -0.0002 (4.17)

[DMSO], Spektrometer: 399.95MHz 8.7231 (2.60); 8.7020 (2.65); 7.5839 (5.94); 7.5803 (6.44); 7.3996 (1.21); 7.3951 (0.92); 7.3789 (9.06); 7.3736 (14.41); 7.3517 (1.29); 4.3427 (0.56); 4.3210 (1.30); 4.3046 (1.60): 4.2997 ( 1.06); 4.2905 (1.28); 4.2690 (0.62); 3.3395 (91.34); 2.9978 (0.50); 2.9928 (1.78): 2.9792 (1.95); 2.9586 (3.54); 2.9451 (3.31 ); 2.9337 (0.34); 2.8990 (3.28); 2.8769 (3.20): 2.8648 ( 1.81 ); 2.8427 (1.73); 2.6726 (0.44); 2.6680 (0.32); 2.5431 (14.37); 2.5261 ( 1.28): 2.5125 (25.1 1 ); 2.5081 (50.63); 2.5036 (67.19): 2.4990 (50.39); 2.4946 (25.68); 2.3303 (0.44); 2.3257 (0.33); 2.0776 (0.56); 1.2350 (16.00); 1.2184 (15.83); 0.0080 (0.33); -

19-10 2,4-dichlor-phenyl CH2 CH(CH3) H 0.0002 (9.83); -0.0085 (0.42)

[DMSO], Spektrometer: 399.95MHz 8.5244 (0.45); 8.5093 (0.87); 8.4941 (0.46); 7.4515 (2.38); 7.4299 (4.35); 7.3812 (4.42); 7.3639 (0.95); 7.3596 (2.39); 3.4804 (3.09); 3.4647 (3.08); 3.3427 (14.46); 2.5438 ( 1.18);

19-1 1 4-chlor-phenyl C(CH3)2 CH2 H 2.5090 (7.49); 2.5047 (9.63); 2.5006 (7.32); 2.0785 (0.56); 1.3199 (16.00); -0.0002 (1.03)

[DMSO], Spektrometer: 399.95MHz 8.5462 (0.47); 8.5307 (0.91); 8.5155 (0.47); 7.5449 (2.56); 7.5392 (2.75); 7.4817 (1.58); 7.4600 (2.57); 7.3986 (1.75); 7.3928 (1.64); 7.3770 (1.09); 7.3712 (1.04); 3.8267 (3.08); 3.8109 (3.06); 3.3406 (18.90); 2.5439 (1.33); 2.5133 (4.42); 2.5090 (8.72); 2.5045 (1 1.48);

19-12 2,4-dichlor-phenyl C(CH3)2 CH2 H 2.5000 (8.64); 2.4959 (4.44); 2.0787 (0.62); 1.4697 (16.00); -0.0002 (1.49)

[DMSO], Spektrometer: 399.95MHz 8.8495 (2.31); 8.8362 (4.26); 8.8228 (2.56); 7.4483 (5.85); 7.4440 (4.95); 7.4299 (8.03): 7.4253 (7.77); 7.4076 (0.52); 7.3783 (4.41 ); 7.3729 (5.50); 7.3599 (6.47); 7.3550 (8.44); 7.3210 (2.68); 7.3168 (3.45); 7.3027 (8.15); 7.2985 (7.66); 7.2865 (9.83); 7.2809 (10.41): 7.2685 (7.22); 7.2633 (6.22); 7.2500 (2.55); 7.2450 ( 1.96); 3.5642 (4.49); 3.5470 (10.21 ); 3.5319 (10.47); 3.5142 (5.54); 3.3436 (133.06); 3.0006 (8.81); 2.9828 (16.00); 2.9651 (8.39); 2.6780 (0.36); 2.6733 (0.48); 2.6688 (0.36); 2.5435 (12.04); 2.5266 (1.84); 2.5131 (28.79); 2.5087 (57.00); 2.5042 (75.11 ); 2.4996 (56.62); 2.4952 (30.49); 2.3356 (0.36);

19-13 2-chlor-phenyl CH2 CH2 H 2.3309 (0.49); 2.3263 (0.37); 2.0778 (1.98); -0.0002 (8.63); -0.0085 (0.47)

[DMSO], Spektrometer: 399.95MHz 8.7831 (1.79); 8.7697 (3.26); 8.7563 (1.81); 8.0167 (0.44); 8.0142 (0.46); 7.7686 (0.56); 7.7640 (1.10); 7.5729 (9.10); 7.5518 (16.00); 7.5455 (9.40); 7.5300 (1.00); 7.2724 (5.03); 7.2675 (4.89); 7.2519 (4.43); 7.2469 (4.33); 3.5517 (2.97); 3.5348 (7.98); 3.5198 (8.24); 3.5032 (3.53); 3.4913 (0.56); 3.3421 (68.88); 2.8729 (5.77); 2.8558 (1 1.58); 2.8387 (5.30); 2.6739 (0.36); 2.5442 (20.13); 2.5269 (1.23): 2.5092 (39.28); 2.5048 (50.84); 2.5003

19-14 3 ,4-dichlor-phenyl CH2 CH2 H (38.03): 2.3314 (0.32); -0.0002 (6.05)

[DMSO], Spektrometer: 399.95MHz 8.791 1 (1.51 ); 8.7773 (2.84); 8.7639 (1.57); 7.4621 (3.80); 7.4574 (7.53); 7.4527 (4.51 ): 7.3510 (16.00); 7.3463 (15.06); 3.5626 (2.41 ); 3.5462 (6.56); 3.5309 (6.73); 3.5146 (2.74); 3.3448 (76.07); 2.8833 (4.62); 2.8665 (9.15); 2.8497 (4.27); 2.5445 (6.75); 2.5270 (0.83);

19-15 3,5- dichlor-pheny 1 CH2 CH2 H 2.5096 (27.94); 2.5051 (36.59); 2.5008 (27.67); 2.0790 (3.29); -0.0002 (3.41 )

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw . Patent-Nr.

[DMSO]. Spektrometer: 399.95MHz 8.7918 (2.09); 8.7786 (3.77); 8.7654 (2.21); 7.3726 (0.45); 7.3575 (3.69); 7.3382 (16.00); 7.3192 (8.92); 7.2947 (4.95); 7.2916 (7.69); 7.2869 (5.41); 7.2749 (2.80); 7.2703 (3.49); 7.2671 (2.30); 7.2343 (6.99); 7.2158 (4.98); 3.5505 (3.89); 3.5331 (9.69); 3.5183 (9.79); 3.501 1 (4.46); 3.3496 (96.29); 2.8786 (7.20); 2.861 1 (14.18); 2.8435 (6.87); 2.8251 (0.35); 2.5450 (9.80); 2.5280 (0.84); 2.5144 (14.12); 2.5101 (28.09); 2.5056 (37.06); 2.5011

19-16 3-chlor-phenyl CH2 CH2 H (27.82); 2.4969 (14.31); 2.0791 (2.50); -0.0002 (3.45)

[DMSO], Spektrometer: 399.95MHz 8.8382 (2.72); 8.8249 (4.94); 8.81 14 (2.83); 7.3493 (3.12); 7.3453 (3.77); 7.3307 (6.31); 7.3261 (7.78); 7.3178 (1.32); 7.31 10 (5.26); 7.3070 (6.13); 7.2978 (2.28); 7.2930 (4.44); 7.2868 (3.36); 7.2783 (4.56); 7.2725 (5.67); 7.2681 (3.20); 7.2589 (3.29); 7.2544 (2.70); 7.1846 (6.09); 7.1640 (12.14); 7.1479 (10.66); 7.1451 (10.10); 7.1411 (5.38); 7.1380 (4.57); 7.1295 (4.67); 7.1266 (4.17); 3.5382 (5.31); 3.5210 (12.15); 3.5055 (12.02); 3.4881 (5.99); 3.3396 (151.75); 2.9086 (8.60); 2.8908 (16.00); 2.8730 (7.82); 2.6771 (0.50); 2.6726 (0.70); 2.6680 (0.54); 2.5430 (16.86); 2.5338 (0.86); 2.5258 (2.20); 2.5124 (39.67); 2.5080 (79.89); 2.5035 (106.15); 2.4989 (79.67); 2.4945 (40.94); 2.3347 (0.48); 2.3302

19-17 2-fluor-phenyl CH2 CH2 H (0.67); 2.3257 (0.51 ); 2.0774 (1.75); 0.0080 (0.57); -0.0002 (16.34); -0.0084 (0.71 )

[DMSO], Spektrometer: 399.95MHz 8.9007 (2.81 ); 8.8864 (5.25); 8.8721 (2.89); 7.3756 (1.65); 7.3588 (3.71 ); 7.3546 (3.45); 7.3378 (7.21 ); 7.3205 (3.71 ); 7.3170 (4.72); 7.3002 (2.18); 7.1 144 (0.95); 7.1 101 (1.39); 7.0980 (10.03); 7.0899 (2.24); 7.0782 ( 16.00); 7.0673 (2.34); 7.0581 (8.70); 7.0458 (1.29); 3.5129 (4.77); 3.4960 (13.06); 3.4802 (13.39); 3.4636 (5.42); 3.3679 (0.36); 3.3420 (107.12); 2.9327 (7.50); 2.9155 (14.53); 2.8983 (6.88); 2.6738 (0.44); 2.6694 (0.33); 2.5443 (0.46); 2.5272 (1.38); 2.5137 (25.06); 2.5094 (50.22); 2.5048 (66.45); 2.5003 (49.73); 2.4958 (25.33); 2.3316 (0.42); 2.3271 (0.32); 0.0079 (0.33); -0.0002 (9.53); -

19-18 2,6-difluor-phenyl CH2 CH2 H 0.0086 (0.39)

[DMSO]. Spektrometer: 399.95MHz 8.9373 (1.36); 8.9229 (2.62); 8.9083 (1.40); 7.4765 (1 1.58); 7.4564 (16.00); 7.3161 (5.43); 7.2970 (5.29); 7.2951 (5.32); 7.2758 (3.58); 3.5576 (2.10); 3.5408 (5.68); 3.5246 (5.85); 3.5080 (2.59); 3.3415 (57.81); 3.1951 (4.63); 3.1777 (8.55); 3.1604 (3.93); 2.5441 (5.45); 2.5270 (0.80); 2.5136 (14.24); 2.5092 (28.83); 2.5046 (38.37); 2.5001 (28.84); 2.4957

19-19 2,6-dichlor-phenyl CH2 CH2 H (14.83); 2.0788 (2.44); -0.0002 (5.53)

[DMSO], Spektrometer: 399.95MHz 8.7964 (2.23); 8.7835 (3.96); 8.7703 (2.26); 7.6628 (0.40); 7.6154 (9.26); 7.6001 (3.27); 7.5966 (3.26); 7.5908 (3.88); 7.5760 (16.00); 7.5625 (9.95); 7.5502 (3.78); 7.5387 (1.89); 7.5262 (1.44); 7.4994 (0.38); 3.5867 (3.96); 3.5695 (10.42); 3.5548 (10.75); 3.5378 (4.57); 3.3419 (134.70): 2.9749 (7.43); 2.9576 (14.97); 2.9403 (6.88); 2.6775 (0.51 ); 2.6729 (0.68); 2.6685 (0.52); 2.5433 (17.34); 2.5263 (2.41); 2.5128 (40.93); 2.5084 (80.03);

3 -(trifluormethyl)- 2.5039 (104.05): 2.4994 (77.50); 2.4950 (39.59); 2.3351 (0.50); 2.3307 (0.68); 2.3262

19-20 phenyl CH2 CH2 H (0.49); 2.0778 (0.93); 0.0080 (0.69); -0.0002 (17.79); -0.0085 (0.76)

[DMSO], Spektrometer: 399.95MHz 8.8177 (2.60); 8.8041 (4.86); 8.7904 (2.63); 7.6831 (13.1 1 ); 7.6630 (16.00); 7.4994

4-(trifluormethyl)- (14.89); 7.4794 (12.39); 3.5812 (4.57); 3.5638 (1 1.19); 3.5489 (1 1.29); 3.5316 (5.14);

19-21 phenyl CH2 CH2 H 3.3418 (176.25); 2.9659 (7.54); 2.9483 (14.53); 2.9307 (6.82); 2.6778 (0.52); 2.6731

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

(0.70); 2.6686 (0.55); 2.5436 (18.36); 2.5266 (2.35); 2.5218 (3.55); 2.5131 (40.06); 2.5087 (80.58); 2.5041 (106.74); 2.4996 (79.60); 2.4952 (40.28); 2.3355 (0.48); 2.3310 (0.68); 2.3266 (0.48); 2.0780 (1.55); 0.0080 (0.58); -0.0002 (17.65); -0.0085 (0.75)

[DMSO], Spektrometer: 399.95MHz 8.8388 (0.56); 8.8252 (1.02); 8.81 10 (0.57); 7.1762 (1.10); 7.1680 (1.57); 7.1600 (2.17); 7.1529 (3.48); 7.1464 (1.52); 7.1401 (1.15); 7.1353 (3.36); 7.1325 (3.75); 7.1270 (1.42); 7.1222 (2.19); 7.1 175 (1.38); 7.1 1 10 (1.65); 3.4793 (1.1 1); 3.4639 (1.94); 3.4568 (1.23); 3.4460 (1.65); 3.4415 (2.06); 3.4267 (1.23); 3.3398 (36.67); 2.8624 (2.18); 2.8427 (2.65); 2.8243 (1.97); 2.5424 (3.80); 2.5253 (0.57); 2.5119 (9.67); 2.5074 (19.48); 2.5029 (25.78);

19-22 2-methyl-phenyl CH2 CH2 H 2.4983 (19.12); 2.4938 (9.54); 2.3216 (16.00); 2.0768 (0.40); -0.0002 (4.25)

2,4,6-trimethyl-

19-23 phenyl CH2 CH2 H

3,4-bismethoxy-

WO-A 1999/24413

19-24 phenyl CH2 CH2 H

[DMSO], Spektrometer: 399.95MHz 8.7893 (1.92); 8.7766 (3.37); 8.7637 (1.96); 7.3294 (4.40); 7.3257 (2.01); 7.3110 (1 1.94); 7.2976 (3.73); 7.2929 (12.13); 7.2650 (10.76); 7.2613 (16.00); 7.2443 (7.92); 7.2347 (4.70); 7.2217 (2.41); 7.2166 (6.34); 7.21 10 (1.64); 7.2026 (1.43); 7.1989 (2.22); 7.1955 (1.20); 3.5342 (4.15); 3.5169 (7.84); 3.5019 (7.46); 3.4986 (7.53); 3.4832 (4.68); 3.3438 (186.18); 2.8650 (7.54); 2.8463 (12.09); 2.8284 (6.88); 2.6766 (0.41); 2.6723 (0.56); 2.6677 (0.44); 2.5427 (12.25); 2.5257 (1.71); 2.5209 (2.48); 2.5121 (30.51); 2.5078 (62.13); 2.5032 (82.86); 2.4987 (62.25); 2.4942 (31.74); 2.3346 (0.36); 2.3300 (0.52);

19-25 phenyl CH2 CH2 H 2.3255 (0.38); 2.0768 (0.71); -0.0002 (9.93); -0.0084 (0.41)

C(CH2-

19-26 4-chlor-phenyl CH2) CH2 H

C(CH2-

19-27 2,4-dichlor-phenyl CH2) CH2 H

C(CH2-

19-28 4-chlor-phenyl CH2 CH2) H

C(CH2-

19-29 2,4-dichlor-phenyl CH2 CH2) H

19-30 4-chlor-phenyl 0 CH2 CH2 H

19-31 2,4-dichlor-phenyl 0 CH2 CH2 H

19-32 4-chlor-phenyl CH2 CH2 CH2 H

19-33 4-chlor-phenyl NCH3 CH2 CH2 H

19-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

19-35 4-chlor-phenyl CH(OCH3) CH2 - H

19-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

Verbindung Nr. 19-37, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8336 (4,16); 7,3653 (6,75); 7,3528 (7,52); 6,9787 (4,74); 6,97 (7,86); 6,9576 (7,44); 6,937 (9,26); 6,9294 (6,33); 3,5478 (4,27); 3,5305 (10,7); 3,5153 (1 1,05); 3,4981 (5,03); 3,3931 (0,38); 3,3266 (812,02); 3,231 1 (0,42); 3,0886 (8,69); 3,0709 (16); 3,0532 (7,58); 2,6701 (3,3); 2,5397 (2,96); 2,5047 (374,78); 2,501 (476,09); 2,3279 (3, 13); 1 ,2346 (0,43);

19-37 2-thienyl CH2 CH2 H -0,0002 (5,83

19-38 3-thienyl CH2 CH2 - H

19-39 2-furyl CH2 CH2 - H

19-40 3-furyl CH2 CH2 - H

19-41 phenyl CH2 CH2 CH(CH3) H

19-42 phenyl CH2 CH2 CH2 H

19-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

19-44 4-t-butyl-phenyl CH2 CH2 CH2 H

19-45 4-methyl-phenyl CH2 CH2 CH2 H

19-46 phenyl CH2 CH2 CH(CH2CH3) H

19-47 2-methoxy-phenyl CH2 CH2 CH2 H

19-48 2-methyl-phenyl CH2 CH2 CH2 H

19-49 3 -methyl-phenyl CH2 CH2 CH2 H

19-50 3-chlor-phenyl CH2 CH2 CH2 H

19-51 2,6-difluor-phenyl CH2 CH2 CH2 H

19-52 4-chlor-phenyl CH2 CH2 CH2 H

19-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

19-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

2,6-dimethyl-

19-55 phenyl CH2 CH2 CH2 H

19-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

19-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

19-58 3 -trifluormethyl- CH2 CH2 CH(CH3) H

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr. phenyl

19-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

19-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

19-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

19-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

2,6-dimethyl-

19-63 phenyl CH2 CH2 CH(CH3) H

4-trifluormethyl-

19-64 phenyl CH2 CH2 CH(CH3) H

19-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

19-66 4-phenoxy-phenyl CH2 CH2 CH2 H

19-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

19-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

19-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

2-difluormethoxy-

19-70 phenyl CH2 CH2 CH(CH3) H

19-71 4-methoxy-phenyl CH2 CH2 CH2 H

19-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

19-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

19-74 4-fluor-phenyl CH2 CH2 CH2 H

19-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

19-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

19-77 2-chlor-phenyl CH2 CH2 CH2 H

19-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Verbindung Nr. 19-79, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8608 (2,19); 8,8474 (4,01); 8,8336 (2,24); 7,3913 (15,36); 7,3875 (15,49); 6,9401 (1 1 ,63); 6,9369 (1 1,98); 6,5738 (0,41); 3,5496 (4,49); 3,5324 (1 1,85); 3,5178 (12, 11); 3,5008 (5,14); 3,3233 (38,67); 3,0726 (0,4); 3,0536 (8,3); 3,0363 (16); 3,0194 (7,18); 2,6761 (0,37); 2,6716 (0,5); 2,667 (0,36); 2,525 (1 ,55); 2,5203 (2,32); 2,51 16 (28,26); 2,5072 (57,01); 2,5026 (75,01); 2,498 (53,73); 2,4935 (25,57); 2,334 (0,36); 2,3294 (0,5);

19-79 5-chlor-2-thienyl CH2 CH2 H 2,3247 (0,37); 1 ,3361 (1 ,12); 1 ,2988 (0,33); 1 ,2586 (0,47); 1 ,2494 (1 ,29); 1 ,2326 (0,32);

Bsp.-Nr. X L ¹ L ² L ³ Y Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw. Patent-Nr.

1,1878 (0,37); 0,008 (2,52); -0,0002 (72,28); -0,0085 (2,36)

Verbindung Nr.19-80, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8846 (2,51); 7,4971 (3,7); 7,4915 (1,85); 7,4753 (16); 7,4611 (12,36); 7,4393 (3,16); 7,4048 (0,67); 4,1116 (0,8); 4,0968 (1,06); 4,0885 (1,33); 4,0736 (1,47); 4,0651 (1,07); 4,0501 (1,02); 4,0414 (0,4); 3,9563 (1,09); 3,9418 (0,97); 3,922 (1,72); 3,9084 (1,42); 3,8182 (1,33); 3,7947 (1,33); 3,763 (0,73); 3,3264 (41,38); 2,6724 (0,32); 2,5117 (19,46); 2,5075 (37,26); 2,5031 (48,06); 2,4986 (35,03); 2,4944 (17,36); 1,3365 (0,91); 1,2492

19-80 4-chlor-phenyl CH(CF3) CH2 H (0,84); 0,0078 (0,39); -0,0002 (9,03); -0,0084 (0,34)

Tabelle 20

Verbindungen der Formel 1-20

1-20

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(0.42); 2.5250 (1.78); 2.51 15 (30.26); 2.5072 (60.19); 2.5026 (80.35); 2.4981 (61.14); 2.4937 (31.77); 2.3339 (0.40); 2.3294 (0.53); 2.3249 (0.40); 1.9899 (1.08); 1.3970 (0.40); 1.1750 (0.57); -0.0002 (4.36)

20-7 2,6-difluorphenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-8 2,6-difluorphenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

20-9 2,6-difluorphenyl 2-thienyl CH2 CH2 - H CAS: 1325338-30-4

20-10 2,6-dichlorphenyl 4-chlor-phenyl CH2 CH2 - H CAS: 925089-79-8

20-11 2,6-dichlorphenyl 2,4-dichlor-phenyl CH2 CH2 - H

20-12 2,6-dichlorphenyl 4-chlor-phenyl CH2 CH2 CH2 H

20-13 2,6-dichlorphenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H

20-14 2,6-dichlorphenyl 4-chlor-phenyl 0 CH2 CH2 H

20-15 2,6-dichlorphenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-16 2,6-dichlorphenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-17 2,6-dichlorphenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

20-18 2,6-dichlorphenyl 2-thienyl CH2 CH2 - H

2-(trifluormethyl)-

20-19 phenyl 4-chlor-phenyl CH2 CH2 H WO-A 2007/108483

2-(trifluormethyl)-

20-20 phenyl 2,4-dichlor-phenyl CH2 CH2 H

2-(trifluormethyl)-

20-21 phenyl 4-chlor-phenyl CH2 CH2 CH2 H

2-(trifluormethyl)-

20-22 phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101975

2-(trifluormethyl)-

20-23 phenyl 4-chlor-phenyl 0 CH2 CH2 H CAS: 1099734-75-4

2-(trifluormethyl)-

20-24 phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

2-(trifluormethyl)-

20-25 phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) H

[CDC13], Spektrometer: 400.13MHz

20-26 2-(trifluormethyl)- 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H 15.1093 (0.48); 8.5572 (0.32); 8.2223 (0.37); 8.1265 (0.34);

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

phenyl 8.1070 (0.32); 7.9339 (0.37); 7.8522 (0.52); 7.8429 (0.54)

7.8277 (0.52); 7.7143 (1.89); 7.6949 (2.09); 7.6744 (1.27) 7.6560 (1.51); 7.6211 (0.88); 7.6017 (2.05); 7.5834 (1.94) 7.5530 (2.36); 7.5335 (3.54); 7.5280 (3.38); 7.5180 (3.37) 7.5123 (3.26); 7.4858 (0.72); 7.4816 (0.65); 7.4670 (0.43) 7.4506 (0.32); 7.4238 (3.85); 7.4204 (6.91 ); 7.4154 (3.78) 7.3909 (1.79); 7.3706 (2.98); 7.3665 (2.66); 7.3589 (0.76) 7.3133 (3.46); 7.2926 (5.56); 7.2884 (5.68); 7.2830 (3.85) 7.2783 (2.62); 7.2593 (320.36); 7.2536 (295.32); 7.2177 (0.33); 6.9953 (1.86); 6.9898 (1.63); 6.2179 (0.40); 6.1986 (1.02); 6.1763 (0.91); 6.0188 (0.64); 5.9948 (0.67); 5.298C (1.05); 5.2922 (0.92); 4.7474 (2.16); 4.7413 (2.28); 4.6122 (2.57); 4.5815 (0.92); 4.5774 (0.92); 4.5589 (0.87); 4.553S (0.75); 4.5099 (0.33); 4.4983 (0.68); 4.4919 (0.54); 4.480S (0.76); 4.4637 (0.62); 4.4577 (0.67); 3.2980 (1 1.54); 3.2925 (1 1.18); 3.2858 (16.00); 3.2804 (14.57); 3.2164 (0.38) 3.2101 (0.38); 3.1971 (0.38); 2.8158 (0.70); 1.5876 (0.41) 1.5736 (0.51); 1.5344 (105.05); 1.5297 (91.91 ); 1.4795 (0.34); 1.4660 (0.32); 1.4098 (4.56); 1.4048 (4.23); 1.392S (4.72); 1.3879 (4.12); 1.3316 (0.33); 1.2535 (0.41 ); 1.1374 (0.33); 1.1237 (0.43); 1.0671 (6.78); 1.0623 (6.09); 1.0495 (6.78); 1.0450 (5.96); 0.8472 (0.37); 0.8209 (0.33); 0.1461 (0.66); 0.1410 (0.64); 0.0189 (0.40); 0.0000 (138.31 )

2-(trifluormethyl)-

20-27 phenyl 2-thienyl CH2 CH2 H CAS: 1180590-25-3

Verbindung Nr. 20-28, Solvent: [DMSO], Spektrometer 399.95MHz

8,6748 (1 ,05); 8,6614 (1 ,96); 8,6484 (1 ,07); 8,3161 (1 1 ,05) 7,7031 (2,15); 7,6962 (2,77); 7,6809 (4,08); 7,6373 (0,88) 7,6324 (1 ,37); 7,6187 (4,41); 7,6137 (6,63); 7,6046 (6,53) 7,5958 (6,35); 7,5769 (1 ,02); 7,5198 (0,34): 7,5038 (3,53) 7,4963 (2,03); 7,4891 (2,75); 7,4822 (2,27); 7,37 (0,96) 7,364 (8,78); 7,3595 (3,57); 7,3481 (4, 13): 7,3431 (16) 7,3375 (2,81); 7,2948 (5,29); 7,2889 (14,58): 7,2679 (8,52) 7, 1559 (7); 7,0167 (3,46); 3,5048 (1 ,84); 3,4874 (4,84) 3,4765 (5,54); 3,4734 (5,65); 3,4591 (2,89): 3,4561 (2,7) 3,3222 (18,88); 3,2983 (2,92); 2,8514 (5,34); 2,8338 (10,46); 2,8163 (4,85); 2,6747 (0,39); 2,6703 (0,56); 2,66i (0,41); 2,5232 (1 ,53); 2,51 (27,61 ); 2,5057 (55,63); 2,5012 (74,31); 2,4968 (56, 19); 2,4925 (29,47); 2,3323 (0,36)

2-(difluormethyl)- 2,3278 (0,49); 2.3236 (0.38); 0,0075 (0,92); -0,0002

20-28 phenyl 4-chlor-phenyl CH2 CH2 H (24,99); -0,0083 (1 ,27)

[DMSO], Spektrometer: 399.95MHz

20-29 2-(difluormethyl)- 2,4-dichlor-phenyl CH2 CH2 - H 8.7190 (1.28); 8.7051 (2.43); 8.6909 (1.28); 7.7105 (1.74);

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ³ Patent-Nr.

phenyl 7.7037 (2.19); 7.6883 (3.14); 7.6439 (0.77); 7.6390 (1.12):

7.6254 (3.53); 7.6203 (5.06); 7.61 12 (5.01 ); 7.6023 (5.49): 7.5964 (7.93); 7.5837 (1.06); 7.5318 (2.92); 7.5244 (1.58): 7.5168 (2.05); 7.5104 (1.63); 7.3970 (0.54); 7.3779 (16.00) 7.3575 (0.34); 7.3534 (0.47); 7.3217 (2.45); 7.1826 (5.41): 7.0434 (2.66); 3.5390 (1.96); 3.5222 (5.35); 3.5071 (5.49): 3.4905 (2.19); 3.3309 (15.16); 2.9732 (4.24); 2.9563 (8.59) 2.9392 (3.74); 2.5240 (1.03); 2.5108 (13.31); 2.506S (25.73); 2.5024 (33.46); 2.4979 (24.60); 2.4935 (12.41): 1.9894 (0.40); -0.0002 (6.46)

Verbindung Nr. 20-30, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6396 [1,14); 8,626 [2,12); 8,6119 [1,17); 8,3162 [7,85); 7,7153 [2,16); 7,7058 (3); 7,6931 (3,96); 7,6482 [0,62); 7,6418 [1,22); 7,6296 [5,26); 7,624 (4,86); 7,6179 (4,58); 7,6107 (4,64); 7,6065 (7,73); 7,593 (2,63); 7,5866 [5,14); 7,5735 (2,46); 7,5628 (1,34); 7,4411 (3,25); 7,3524 (9,08); 7,3478 (3,61); 7,3363 (4,21); 7,3314 (16); 7,3257 (2,7); 7,3017 (7,09); 7,2734 (14,23); 7,2524 (8,49); 7,1622 (3,5); 4,0381 (0,37); 4,0204 (0,36); 3,3229 (26,39); 3,2987 (1,9); 3,2701 (2,08); 3,2532 (5,25); 3,239 (5,87); 3,2222 (2,68); 2,6749 (0,45); 2,6707 (0,62); 2,666 (0,56); 2,6531 (4,88); 2,6344 [7,24); 2,6147 (5,28); 2,5238 (1,6); 2,5103 (28,34); 2,5061 [56,45); 2,5016 (75); 2,4972 (56,44); 2,493 [29,4); 2,3331 (0,35); 2,3285 (0,47); 2,3239 (0,38); 1,9888 (1,6); 1,8391 (1,47); 1,8213 (4,26); 1,8021 [5,49); 1,7837 (4,14); 1,7661 [1,29);

2-(difluormethyl)- 1,1928 (0,42); 1,1749 [0,84); 1,1571 (0,42); 0,0079

20-30 henyl 4-chlor-phenyl CH2 CH2 CH2 H (0,76); -0,0002 (21,11); -0,0082 (0,96)

Verbindung Nr. 20-31, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6946 (2,25); 8,6809 [4,24); 8,6675 (2,34); 8,3163 [4,8); 7,7197 (3,37); 7,7092 [5,17); 7,6976 (6,25); 7,6532 [0,86); 7,6458 (1,95); 7,6353 (8,89); 7,6283 (8,28); 7,6232 [5,97); 7,618 (8,56); 7,6121 (16); 7,6058 (6,22); 7,6 [9,94); 7,5868 (4,58); 7,577 (12,69); 7,5719 (13,05); 7,4441 [5,22); 7,437 (7,39); 7,4163 (15,96); 7,3907 (10,52); 7,3855 (10,3); 7,3701 (4,41); 7,3649 (4,49); 7,3526 (0,49); 7,3314 (0,58); 7,3048 (10,58); 7,2733 (0,57); 7,2534 (0,37); 7,1654 (5,22); 3,322 (64,94); 3,3093 (4,55); 3,2923 (9,46); 3,2775 (9,74);

2-(difluormethyl)- 3,2608 (4,23); 3,2401 (0,35); 2,7636 (7,41); 2,7447

20-31 phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H (9,82); 2,7249 (8); 2,6755 (0,77); 2,671 (1,05); 2,6667

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

[0,82); 2,5242 [3,23); 2,5106 [53,74); 2,5064 [108,21); 2,5019 [145,28); 2,4974 [113,32); 2,3332 [0,68); 2,3287 [0,95); 2,3242 [0,74); 1,9889 [1,04); 1,8355 [2,26); 1,8179 [6,19); 1,7987 [7,79); 1,7798 [5,96); 1,7624 [1,91); 1,3974 [1,62); 1,1751 [0,55); 0,0079 [1,85); - 0,0002 [48,24); -0,0083 [2,91)

2-(difluormethyl)-

20-32 phenyl 4-chlor-phenyl 0 CH2 CH2 H

Verbindung Nr. 20-33, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8283 [2,04); 8,8146 [3,93); 8,8013 [2,07); 8,3162 [6,62); 7,7265 [3,04); 7,7188 [4,15); 7,7045 [5,84); 7,6591 (1,2); 7,6529 (2); 7,6413 [5,28); 7,6359 [8,17); 7,6281 [6,64); 7,6183 [10,98); 7,6148 [8,31); 7,598 (8,08); 7,5819 [14,05); 7,5754 (14,37); 7,4377 [4,62); 7,3934 (6); 7,387 [5,67); 7,3713 (8); 7,3648 [7,77); 7,2989 (10,04); 7,2444 [13,18); 7,2221 (9,93); 7,1599 [4,98); 4,2386 (7,22); 4,2244 (16); 4,2102 (8,01); 4,0381 [0,51); 4,0203 (0,46); 3,6674 (3,5); 3,6535 (10,13); 3,6396 [10,08); 3,6255 (3,54); 3,3229 [27,12); 3,2991 (1,99); 2,6753 [0,45); 2,6709 (0,61); 2,6665 [0,45); 2,5239 (1,84); 2,5106 [33,33); 2,5063 (66,36); 2,5018 [87,82); 2,4973 (65,39); 2,4931 [33,55); 2,3331

2-(difluormethyl)- (0,41); 2,3286 [0,58); 2,3242 (0,44); 1,9889 [1,87);

1,1928 (0,5); 1,175 [0,98); 1,1572 (0,47); 0,0076 [1,17);

20-33 phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H -0,0002 (32,23); -0,0084 (1,5)

2-(difluormethyl)-

20-34 phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) H

2-(difluormethyl)-

20-35 phenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) H

2-(difluormethyl)-

20-36 phenyl 2-thienyl CH2 CH2 H

20-37 2-fluor-phenyl 4-chlor-phenyl CH2 CH2 - H CAS: 303091-97-6

20-38 2-fluor-phenyl 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

20-39 2-fluor-phenyl 4-chlor-phenyl CH2 CH2 CH2 H CAS: 932215-55-9

20-40 2-fluor-phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H

20-41 2-fluor-phenyl 4-chlor-phenyl 0 CH2 CH2 H CAS: 1327454-26-1

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

20-42 2-fluor-phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-43 2-fluor-phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-44 2-fluor-phenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

20-45 2-fluor-phenyl 2-thienyl CH2 CH2 - H CAS: 883059-03-8

20-46 2-chlor-phenyl 4-chlor-phenyl CH2 CH2 - H CAS: 329920-38-9

20-47 2-chlor-phenyl 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

20-48 2-chlor-phenyl 4-chlor-phenyl CH2 CH2 CH2 H CAS: 928982-63-2

20-49 2-chlor-phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H

20-50 2-chlor-phenyl 4-chlor-phenyl 0 CH2 CH2 H

20-51 2-chlor-phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-52 2-chlor-phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

[CDC13], Spektrometer: 400.13MHz 7.6736 (0.75); 7.6688 (0.75); 7.6552 (0.96); 7.6510 (0.83); 7.5184 (0.71); 7.4732 (0.65); 7.4702 (0.70); 7.4516 (0.79); 7.4131 (2.72); 7.4059 (2.52); 7.4009 (2.52); 7.3930 (1.90); 7.3692 (1.87); 7.3666 (1.90); 7.3511 (1.79); 7.3465 (1.53); 7.3332 (1.83); 7.3288 (1.48); 7.3173 (2.79); 7.3090 (0.44); 7.2987 (1.25); 7.2944 (1.19); 7.2798 (0.97); 7.2614 (104.22); 7.2596 (120.45); 7.2462 (1.24); 7.2429 (1.00); 7.2254 (0.53); 7.2092 (1.93); 6.9957 (0.69); 6.6293 (0.40); 6.6066 (0.42); 6.4017 (0.32); 4.7763 (1.27); 4.7674 (1.36); 4.6373 (1.23); 4.6318 (1.33); 4.6097 (0.40); 4.6020 (0.41); 4.5934 (0.37); 4.5860 (0.33); 4.5328 (0.33); 4.5227 (0.35); 4.5170 (0.49); 4.4993 (0.33); 3.3130 (16.00); 2.0058 (1.08); 2.0039 (1.22); 1.5441 (61.86); 1.5428 (64.29); 1.4920 (0.87); 1.4336 (3.42); 1.4167 (3.37); 1.0931 (3.97); 1.0760

20-53 2-chlor-phenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) H (3.96); 0.0018 (37.93); 0.0000 (42.74)

20-54 2-chlor-phenyl 2-thienyl CH2 CH2 - H CAS: 883059-11-8

20-55 2-brom-phenyl 4-chlor-phenyl CH2 CH2 - H CAS: 329920-42-5

20-56 2-brom-phenyl 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

20-57 2-brom-phenyl 4-chlor-phenyl CH2 CH2 CH2 H CAS: 931976-92-0

20-58 2-brom-phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H

20-59 2-brom-phenyl 4-chlor-phenyl 0 CH2 CH2 H CAS: 296273-47-7

20-60 2-brom-phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

20-61 2-brom-phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-62 2-brom-phenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

20-63 2-brom-phenyl 2-thienyl CH2 CH2 - H

20-64 2-iod-phenyl 4-chlor-phenyl CH2 CH2 - H WO-A 2001/066553

20-65 2-iod-phenyl 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

20-66 2-iod-phenyl 4-chlor-phenyl CH2 CH2 CH2 H CAS : 932215-61-7

20-67 2-iod-phenyl 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101975

20-68 2-iod-phenyl 4-chlor-phenyl 0 CH2 CH2 H

20-69 2-iod-phenyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-70 2-iod-phenyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-71 2-iod-phenyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

20-72 2-iod-phenyl 2-thienyl CH2 CH2 - H CAS : 1180850-78-5

20-73 2-chlor-3-pyridyl 4-chlor-phenyl CH2 CH2 - H WO-A 2007/108483

20-74 2-chlor-3-pyridyl 2,4-dichlor-phenyl CH2 CH2 - H EP1787981, WO-A 2006/009054

20-75 2-chlor-3-pyridyl 4-chlor-phenyl CH2 CH2 CH2 H

20-76 2-chlor-3-pyridyl 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101976

20-77 2-chlor-3-pyridyl 4-chlor-phenyl 0 CH2 CH2 H CAS : 1280706-56-0

20-78 2-chlor-3-pyridyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-79 2-chlor-3-pyridyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

[CDC 13], Spektrometer: 400 13MHz 16.666 1 (0.46); 16.2155 (0.45); 14.3579 (0.72); 14.3561 (1.20) 10.0965 (0.56); 9.5807 (0.46); 8.4869 (1.28) 8.4816 (1.34) 8.4749 (1.32); 8.4696 (1.39); 8.4501 (0.93) 8.4454 (0.77) 8.4380 (0.97); 8.1345 (1.29); 8.1292 (1.43) 8.1 154 (1.43) 8.1099 (1.41); 7.9452 (0.96); 7.9403 (0.86) 7.9257 (0.63) 7.9212 (0.78); 7.5924 (0.48); 7.5606 (0.45) 7.5194 (4.16) 7.4235 (2.42); 7.4184 (3.00); 7.41 15 (2.07) 7.4060 (1.55) 7.3936 (2.33); 7.3783 (1.77); 7.3664 (1.55) 7.3592 (1.82) 7.3473 (1.74); 7.3412 (0.95); 7.3317 (1.38) 7.3266 (1.27) 7.3207 (2.05); 7.3093 (4.38); 7.3020 (1.92) 7.2897 (1.72) 7.2807 (1.68); 7.2751 (2.63); 7.2742 (2.29) 7.2717 (3.76) 7.2700 (5.00); 7.2693 (5.79); 7.2685 (6.16) 7.2676

20-80 2-chlor-3-pyridyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) H (6.85) 7.2667 (8.28); 7.2606 (749.95); 7.2502 (7.89);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7.2486 (6.63); 7.2478 (6.57); 7.2453 (4.22); 7.2445 (4.18) 7.2420 (3.82); 7.2379 (2.61); 7.2363 (2.79); 7.2258 (1.10) 7.2208 (1.46); 7.2120 (2.36); 6.9966 (4.06); 6.9538 (0.61) 6.9282 (0.56); 6.8835 (0.48); 4.7785 (1.76); 4.7690 (2.00) 4.6423 (1.1 1); 4.6357 (1.29); 4.6061 (0.58); 4.6031 (0.62) 4.5799 (0.63); 4.5274 (0.48); 4.5181 (0.56); 3.7400 (0.57) 3.3350 (9.58); 3.3291 (16.00); 3.3087 (0.53); 2.3093 (0.53) 2.0635 (0.49); 1.6750 (0.49); 1.5915 (1.09); 1.543S (268.09); 1.5096 (0.86); 1.4971 (0.81); 1.4603 (0.46) 1.4479 (3.68); 1.4310 (3.73); 1.2843 (0.47); 1.1624 (0.51) 1.1046 (0.47); 1.0955 (6.04); 1.0783 (5.92); 1.0485 (0.63) 0.8443 (0.51); 0.8276 (0.55); 0.1455 (1.37); 0.0487 (1.59) 0.0372 (0.82); 0.0331 (0.73); 0.0193 (1.22); 0.0152 (1.53) 0.0079 (10.51); 0.0053 (5.58)

20-81 2-chlor-3-pyridyl 2-thienyl CH2 CH2 - H CAS: 1016515-62-0

20-82 3-chlor-2-pyridyl 4-chlor-phenyl CH2 CH2 - H

20-83 3-chlor-2-pyridyl 2,4-dichlor-phenyl CH2 CH2 - H

20-84 3-chlor-2-pyridyl 4-chlor-phenyl CH2 CH2 CH2 H

20-85 3-chlor-2-pyridyl 2,4-dichlor-phenyl CH2 CH2 CH2 H

20-86 3-chlor-2-pyridyl 4-chlor-phenyl 0 CH2 CH2 H

20-87 3-chlor-2-pyridyl 2,4-dichlor-phenyl 0 CH2 CH2 H

20-88 3-chlor-2-pyridyl 4-chlor-phenyl CH(OCH3) CH(CH3) - H

20-89 3-chlor-2-pyridyl 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

Verbindung Nr. 20-90, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8102 (2); 8,7969 [3,57); 8,7829 [2,05); 8,5555 [9,71); 8,5521 [10,14); 8,5439 [10,23); 8,5405 [10,17); 8,0358 [9,45); 8,0324 [9,67); 8,0153 [10,63); 8,0119 [10,2); 7,5563 [11,43); 7,5447 [10,84); 7,5358 [10,42); 7,5242 (10,27); 7,3562 [8,94); 7,3527 [8,99); 7,3439 [9,92); 7,3403 [9,64); 7,3326 [0,52); 7,3228 [0,35); 6,9758 (6,3); 6,9673 [12,58); 6,9636 (5,06); 6,9549 (16); 6,9513 (9,59); 6,948 [10,68); 6,9428 (4,7); 6,9406 (3,88); 3,5307 (5,16); 3,5157 [6,98); 3,5129 (10,36); 3,4982 [10,3); 3,4943 (7,68); 3,4795 [6,03); 3,3275 (282,63); 3,2872 [0,32); 3,074 (8,9); 3,056 [15,41); 3,0375 (7,59); 2,8814 [0,38); 2,6794 (0,35); 2,6752 [0,75); 2,6706 (1,03); 2,6661 [0,73); 2,6614 (0,34);

20-90 3-chlor-2-pyridyl 2-thienyl CH2 CH2 H 2,5409 (63,33); 2,524 (3,09); 2,5193 (4,77); 2,5107

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(56,86); 2,5062 (114,9); 2,5015 (153,32); 2,4969 (111,2); 2,4924 (52,61); 2,3375 (0,35); 2,3329 (0,75); 2,3283 (1,01); 2,3237 (0,73); 2,319 (0,33); 2,0743 (0,43); 0,008 (0,54); -0,0002 (16,04); -0,0085 (0,45)

Verbindung Nr. 20-91, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5671 (3,2); 8,5539 (5,77); 8,5406 (3,33); 7,7868 (7,95); 7,7672 (10,56); 7,7376 (3,51); 7,719 (9,03); 7,7007 (6,5); 7,6564 (6,19); 7,6373 (8,13); 7,6183 (3,11); 7,5222 (9,51); 7,5036 (8,09); 7,3257 (8,36); 7,3238 (8,96); 7,313 (9,28); 7,311 (9,56); 6,9584 (7,59); 6,9499 (9,97); 6,9457 (8,03); 6,9371 (9,24); 6,8814 (10,45); 6,8744 (8,56); 3,3267 (153,05); 3,2886 (5,72); 3,2718 (14,21); 3,2569 (14,23); 3,2403 (5,99); 2,8762 (9,58); 2,8572 (16); 2,838 (10,49); 2,6745 (0,73); 2,67 (0,92); 2,6657 (0,72); 2,5405 (11,03); 2,5052 (95,98); 2,5008 (128,32); 2,4965 (100,07); 2,332 (0,62); 2,3276 (0,83); 2,3234 (0,63); 1,8648 (2,98); 1,8472 (9,01);

2-(difluomiethyl)- 1,8282 (11,83); 1,8098 (8,87); 1,7923 (2,72); -0,0002

20-91 henyl 2-thienyl CH2 CH2 CH2 H (2,25)

Verbindung Nr. 20-92, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5928 (3,25); 8,5793 (6,03); 8,5658 (3,34); 7,7853

(8.08) ; 7,7657 (10,72); 7,7418 (3,66); 7,7231 (9,13); 7,7045 (6,51); 7,6573 (6,29); 7,6382 (8,15); 7,6194

(3.09) ; 7,5091 (9,48); 7,4904 (8,06); 7,3579 (1,6); 7,3408 (3,76); 7,3374 (3,57); 7,3202 (7,08); 7,2995 (4,71); 7,2825 (2,12); 7,128 (0,47); 7,1102 (1,39); 7,0972 (10,08); 7,0776 (16); 7,0578 (8,46); 7,0441 (1,14); 6,5523 (0,52); 3,3313 (62,96); 3,2829 (4,85); 3,2659 (11,59); 3,2502 (11,76); 3,2333 (5,14); 2,7073 (7,03); 2,688 (10,99); 2,6683 (8,03); 2,5423 (22,3); 2,5072 (47,4); 2,5028 (62,7); 2,4985 (48,22); 2,3296

2-(difluormethyl)- (0,41); 1,7824 (2,61); 1,764 (7,07); 1,745 (9,35); 1,7261

20-92 phenyl 2,6-difluor-phenyl CH2 CH2 CH2 H (6,81); 1,708 (2,31); -0,0002 (1,23)

Verbindung Nr. 20-93, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6718 (3,1); 8,6585 (5,6); 8,6454 (3,22); 8,4758 (8,48); 8,471 (9,08); 8,4638 (9,26); 8,459 (9,1); 7,9041 (8,97); 7,8993 (9,17); 7,8853 (10,25); 7,8805 (9,87); 7,5068 (9,8); 7,4947 (9,77); 7,488 (9,35); 7,4759 (8,93); 7,3282 (8,94); 7,3254 (8,82); 7,3154 (9,9); 7,3127 (9,38); 6,9597 (7,48); 6,9512 (10,11); 6,9471 (7,7); 6,9385

20-93 2-chlor-3-pyridyl 2-thienyl CH2 CH2 CH2 H (9,32); 6,8921 (10,36); 6,8841 (8,46); 3,3337 (192,94);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

3,3095 [6,23); 3,2929 [14,51); 3,278 [14,87); 3,2615 [6,02); 2,908 [9,61); 2,8889 (16); 2,8698 [10,47); 2,6707 [0,52); 2,6663 [0,39); 2,541 [29,76); 2,5239 [1,58); 2,5059 [56,79); 2,5016 [75,45); 2,4972 [58,03); 2,3284 [0,49); 1,8893 [2,96); 1,8719 [9,13); 1,8529

[11,78); 1,8344 [8,87); 1,817 [2,72)

Verbindung Nr. 20-94, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7031 [3,23); 8,6894 [5,89); 8,6758 [3,24); 8,4912 [0,37); 8,4766 [8,64); 8,4718 [9,18); 8,4646 [9,27); 8,4598 [9,04); 7,8796 [8,87); 7,8748 [9,07); 7,8608 (10,08); 7,856 [9,71); 7,5112 (9,99); 7,4991 [9,83); 7,4924 (9,19); 7,4803 [8,75); 7,3586 (1,61); 7,3415 [3,75); 7,3381 (3,57); 7,3208 [7,06); 7,3001 (4,69); 7,2832 [2,11); 7,1305 (0,47); 7,115 [0,99); 7,1107 (1,45); 7,0978 [10,04); 7,0781 (16); 7,0582 [8,35); 7,0447 (1,11); 4,1111 [0,33); 3,3304 (78,24); 3,3037 [5,07); 3,2867 (12,08); 3,2713 [12,23); 3,2544 (5,21); 2,7326 (7); 2,7132 (10,88); 2,6935 [7,67); 2,6775 (0,65); 2,6724 [0,63); 2,5425 (6,02); 2,5075 [55,51); 2,5031 (73,74); 2,4987 [56,58); 2,3344 (0,36); 2,3301 [0,48); 1,8048 (2,62); 1,7866 [7,19); 1,7674 (9,3);

20-94 2-chlor-3-pyridyl 2,6-difluor-phenyl CH2 CH2 CH2 H 1,7485 (6,94); 1,7306 (2,32); -0,0002 (1,2)

Verbindung Nr. 20-95, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7866 (2,67); 8,7735 [4,65); 8,7608 (2,77); 7,5484 [1,64); 7,5316 (3,62); 7,5274 (3,5); 7,5105 (7,02); 7,4937 [3,64); 7,4895 (4,22); 7,4728 [1,91); 7,3278 (8,06); 7,3251 [7,93); 7,3151 (8,92); 7,3124 [8,41); 7,1979 (1,96); 7,1903 [11,27); 7,1708 (16); 7,1504 [9,58); 7,1424 (1,96); 6,9575 [7,04); 6,949 (9,15); 6,9448 [7,26); 6,9363 (8,37); 6,8801 [9,17); 6,8781 (9,16); 6,8718 (7,9); 3,3278 (164,47); 3,3094 (6,3); 3,2927 (13,31); 3,278 [13,4); 3,2615 (5,42); 2,879 (8,6); 2,86 (14,17); 2,8408 [9,35); 2,6748 (0,7); 2,6704 [0,92); 2,666 (0,69); 2,5407 [13,91); 2,5057 (97,37); 2,5013 (129,07); 2,4969 (98,84); 2,3324 [0,62); 2,3281 (0,85); 2,3238 [0,63); 1,8648 (2,72); 1,8476 [8,31); 1,8284

20-95 2,6-difluorphenyl 2-thienyl CH2 CH2 CH2 H (10,51); 1,81 (8); 1,7926 (2,48); -0,0002 (1,8)

Verbindung Nr. 20-96, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8193 (2,86); 8,8061 [5,16); 8,793 (3,04); 7,5468 [1,59); 7,53 (3,62); 7,5258 [3,55); 7,5089 (6,85); 7,492

20-96 2,6-difluorphenyl 2,6-difluor-phenyl CH2 CH2 CH2 H (3,73); 7,488 (4,21); 7,4712 (1,86); 7,3558 (1,44);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,3389 [3,36); 7,3353 [3,29); 7,3181 [6,42); 7,2975 [4,31); 7,2805 [1,93); 7,2155 [0,34); 7,1946 [2,39); 7,187 [11,02); 7,1673 (16); 7,1471 [9,84); 7,1393 [2,31); 7,1273 [0,75); 7,1048 [1,37); 7,0915 [9,02); 7,0719 [14,49); 7,052 [7,74); 7,0387 [1,18); 3,3299 (80,97); 3,3089 (5,1); 3,2919 (11,57); 3,2766 [11,69); 3,2599 (4,94); 2,7096 [6,49); 2,6901 (9,8); 2,6705 [7,65); 2,5422 (27,45); 2,5071 [59,63); 2,5028 (79,63); 2,4985 [62,94); 2,3297 (0,53); 2,3252 [0,41); 1,7748 (2,41); 1,757 [6,62); 1,7375 (8,36); 1,7184 [6,52); 1,7008 (2,23); -0,0002 (1,19)

Verbindung Nr. 20-97, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6527 (1,15); 8,6382 [2,18); 8,6237 (1,13); 8,524 [4,77); 8,5206 (5,04); 8,5124 [5,01); 8,509 (4,91); 8,0051 [4,61); 8,0017 (4,68); 7,9846 [5,17); 7,9812 (4,91); 7,5252 [5,46); 7,5136 (5,22); 7,5047 [4,94); 7,4931 (4,93); 7,3712 [0,73); 7,3657 (5,87); 7,3604 [2,25); 7,3496 (3,36); 7,3442 (15); 7,3388 (2,37); 7,3198 [2,39); 7,3145 (13,76); 7,3091 [3,14); 7,2982 (2,16); 7,2931 [5,61); 3,4579 (0,52); 3,4427 [0,66); 3,4397 (0,69); 3,4249 [2,62); 3,4074 (4,48); 3,3919

[4.37) ; 3,3747 (2,74); 3,3601 [0,67); 3,3565 (0,84); 3,3416 [1,25); 3,3261 (91,33); 3,0787 [1,24); 3,0609 (2,5); 3,0431 [2,43); 3,0252 (1,12); 2,6755 [0,33); 2,6709 (0,44); 2,5411 [9,44); 2,5242 (1,49); 2,5194

[2.38) ; 2,5109 (25,29); 2,5064 [50,25); 2,5018 (66,57); 2,4972 [48,4); 2,4926 (23,09); 2,3286 [0,42); 2,0748

20-97 3-chlor-2-pyridyl 4-chlor-phenyl CH(CH3) CH2 H (0,57); 1,2383 (16); 1,2208 (15,67); -0,0002 (8,46)

Verbindung Nr. 20-98, Solvent: [DMSO], Spektrometer: 399.95MHz

20,0109 (1,35); 3,3257 (4454,79); 2,6796 (5,86); 2,6751 [11,85); 2,6704 (16); 2,6658 [11,7); 2,6612 (5,68); 2,5407 [14,72); 2,5238 (50,32); 2,5191 [79,38); 2,5105 (854,78); 2,5059 (1704,74); 2,5013 (2262,73); 2,4967 (1622,75); 2,4921 (753); 2,3373 [4,95); 2,3327 (10,69); 2,3281 [14,85); 2,3235 (10,35); 2,3188 [4,51); 2,2876 (1,26); 2,0741 [8,13); 1,2978 (1,71); 1,2582 [2,59); 1,1467 (1,48); 0,008 [9,02); -0,0001 (230,2); -0,0085

20-98 3-chlor-2-pyridyl 2,6-difluor-phenyl CH2 CH2 H I ]

Verbindung Nr. 20-99, Solvent: [DMSO], Spektrometer: 399.95MHz

8,879 [1,24); 8,8644 (2,34); 8,85 [1,22); 8,5555 (4,98);

20-99 3-chlor-2-pyridyl 2,6-dichlor-phenyl CH2 CH2 H 8,5521 (5,26); 8,5439 (5,18); 8,5405 (5,19); 8,0368

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(4,91); 8,0334 (4,98); 8,0163 (5,42); 8,0129 (5,24); 7,5576 (5,7); 7,546 (5,41); 7,5371 (5,14); 7,5255 (5,14); 7,4713 (11,44); 7,4513 (16); 7,3098 (5,63); 7,2908 (5,21); 7,2887 (5,09); 7,2695 (3,67); 3,4902 (2,13); 3,4747 (4,25); 3,4665 (2,48); 3,4568 (3,35); 3,4519 (4,42); 3,4374 (2,69); 3,3616 (0,34); 3,3289 (196,23); 3,2997 (0,39); 3,1885 (4,92); 3,1741 (3,82); 3,1684 (5,31); 3,1506 (3,77); 2,9928 (0,4); 2,6759 (0,43); 2,6714 (0,6); 2,6667 (0,44); 2,5417 (3,46); 2,5247 (2,02); 2,5114 (34,95); 2,5069 (69,4); 2,5023 (91,93); 2,4977 (67,13); 2,4932 (32,31); 2,3337 (0,43); 2,3291 (0,59); 2,3244 (0,42); -0,0002 (6,28)

Verbindung Nr. 20-100, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7168 (2,89); 8,7033 (5,09); 8,6899 (2,89); 8,5659 (0,32); 8,555 (11,33); 8,5517 (11,89); 8,5434 (11,97); 8,54 (11,87); 8,5289 (0,39); 8,32 (0,32); 8,0402 (11,39); 8,0368 (11,42); 8,0197 (12,72); 8,0163 (12,03); 7,8261 (0,34); 7,5487 (12,99); 7,537 (12,49); 7,5281 (11,98); 7,5165 (11,77); 7,5051 (0,34); 7,3264 (10,74); 7,3234 (10,9); 7,3136 (11,97); 7,3106 (11,62); 6,9568 (8,97); 6,9483 (11,96); 6,9441 (8,95); 6,9356 (11,41); 6,923 (0,42); 6,8941 (10,56); 6,8915 (10,87); 6,8889 (6,99); 6,8857 (8,56); 6,8831 (8,05); 6,5773 (1,9); 3,3506 (0,55); 3,3346 (35,61); 3,3259 (6,76); 3,3089 (15,07); 3,2939 (15,13); 3,277 (6,37); 2,89 (9,7); 2,8708 (16); 2,8518 (10,42); 2,6762 (0,48); 2,6717 (0,66); 2,6671 (0,49); 2,5417 (0,46); 2,5248 (2,32); 2,5115 (35,66); 2,5071 (71,08); 2,5025 (94,26); 2,498 (70,42); 2,4936 (35,15); 2,3337 (0,46); 2,3292 (0,62); 2,3248 (0,45); 1,8933 (3,31); 1,8757 (9,39); 1,8565 (11,85); 1,8381 (9,11); 1,8205 (2,9); 0,008 (2,01); -0,0002 (56,72); -

20-100 3-chlor-2-pyridyl 2-thienyl CH2 CH2 CH2 H 0,0085 (2,12)

[CD3CN], Spektrometer: 399.95MHz

7.4371 (1.76); 7.4346 (2.53); 7.4334 (2.70); 7.4310 (2.77) 7.4242 (0.85); 7.4175 (6.85); 7.4155 (8.44); 7.4135 (8.55) 7.41 15 (8.75); 7.4090 (6.49); 7.4019 (5.40); 7.3945 (5.99) 7.3873 (8.41); 7.3828 (1.48); 7.3746 (2.32); 7.3722 (1.86) 7.3678 (7.13); 7.3571 (1 1.42); 7.3540 (16.00); 7.350 (15.24); 7.3395 (5.36); 7.3353 (4.89); 7.3312 (1.42); 7.3204 (1.20); 7.3163 (1.32); 7.3126 (1.46); 7.2960 (2.78); 7.2915 (2.65); 7.2793 (1.79); 7.2750 (5.55); 7.2707 (2.28); 7.2582 (2.69); 7.2541 (3.55); 7.2375 (1.70); 7.0013 (0.80); 6.9969

20-101 2-chlor-phenyl 2,6-difluor-phenyl CH2 CH2 H (1.09); 6.9848 (6.92); 6.9831 (6.20); 6.9765 (1.59); 6.9645

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(1 1.84); 6.9530 (1.94); 6.9442 (6.83); 6.9316 (2.17); 6.9281 (2.07); 6.9115 (1.55); 3.5955 (5.13); 3.5786 (14.04); 3.5623 (14.32); 3.5456 (5.75); 2.9814 (6.83); 2.9643 (12.91); 2.9471 (6.19); 2.1620 (33.13); 1.9649 (1.44); 1.9588 (1.82); 1.9530 (16.67); 1.9469 (31.95); 1.9407 (45.11); 1.9345 (31.42); 1.9283 (16.29); 1.3720 (1.91); 1.3402 (0.53); 1.2846 (0.71); 1.2761 (2.14); 0.0081 (0.86); -0.0002 (24.95); -0.0086 (1.01 )

[CD3CN], Spektrometer: 399.95MHz 7.6127 (5.77); 7.6091 (6.50); 7.6036 (1.81); 7.6006 (1.89) 7.5894 (8.99); 7.4072 (2.86); 7.4043 (3.07); 7.3975 (0.67) 7.3874 (7.17); 7.3868 (7.21); 7.3850 (5.95); 7.3800 (1.03) 7.3700 (7.26); 7.3670 (6.89); 7.3272 (2.78); 7.3224 (9.67) 7.3175 (10.94); 7.3135 (10.59); 7.3053 (8.77); 7.3029 (6.71); 7.2995 (9.00); 7.2941 (8.09); 7.2876 (4.57); 7.2827 (3.70); 7.2764 (6.42); 7.2722 (2.55); 7.2597 (3.10); 7.2555

(3.90) ; 7.2390 (1.87); 7.0054 (0.85); 7.0009 (1.16); 6.9888 (7.92); 6.9806 (1.72); 6.9686 (13.18); 6.9570 (1.89); 6.9484 (7.10); 6.9356 (1.53); 6.9323 (1.34); 6.8941 (1.93); 5.4488 (1.32); 3.5870 (5.83); 3.5700 (15.66); 3.5535 (16.00) 3.5367 (6.53); 2.9835 (7.84); 2.9662 ( 14.68); 2.9489 (7.08) 2.171 1 (1 18.64); 2.1083 (0.38); 1.9652 (2.04); 1.9591 (2.81); 1.9533 (23.58); 1.9472 (44.73); 1.9410 (62.83) 1.9348 (43.82); 1.9286 (22.83); 1.7694 (0.36); 1.3719

(1.91) ; 1.2762 (2.14); 0.0080 (0.99); -0.0002 (26.58);

20-102 2-brom-phenyl 2,6-difluor-phenyl CH2 CH2 H 0.0084 (1.21)

[CD3CN], Spektrometer: 399.95MHz 7.8836 (7.62); 7.8815 (7.99); 7.8638 (8.08); 7.8616 (8.34) 7.4300 (4.03); 7.4273 (4.06); 7.41 12 (9.07); 7.4086 (8.97) 7.3988 (0.51); 7.3923 (5.66); 7.3897 (5.52); 7.3135 (1.53) 7.2968 (3.17); 7.2926 (3.16); 7.2800 (2.15); 7.2759 (6.51) 7.2718 (2.72); 7.2607 (10.21 ): 7.2568 (1 1.57); 7.242C (6.94); 7.2380 (8.66); 7.1493 (4.80); 7.1451 (4.63); 7.1303 (7.26); 7.1261 (7.09); 7.1 109 (4.00); 7.1066 (3.77); 7.007- (0.83); 7.0033 (1.16); 6.9910 (8.12); 6.9709 (13.41); 6.9594 (1.75); 6.9508 (7.13); 6.9381 (1.31 ); 6.9189 (0.46); 6.898 ^" (0.50); 6.8553 (1.92); 6.8084 (0.38); 5.4481 (0.51); 3.576 ^_ (6.29); 3.5597 (15.88); 3.5432 (16.00); 3.5263 (6.89) 2.9893 (8.07); 2.9719 (14.90); 2.9545 (7.28); 2.1633 (47.92); 1.9649 (1.38); 1.9587 (1.95); 1.9530 (16.38) 1.9469 (30.82); 1.9407 (43.20); 1.9345 (30.09); 1.9283 (15.53); 1.4359 (0.37); 1.3720 (2.63); 1.2846 (0.41); 1.276C

20-103 2-iod-phenyl 2,6-difluor-phenyl CH2 CH2 H (2.90); 0.0080 (0.73); -0.0002 (20.73); -0.0085 (0.84)

[CD3CN], Spektrometer: 399.95MHz

20-104 2-(trifluormethyl)- 2,6-difluor-phenyl CH2 CH2 - H 7.7400 (6.16); 7.7205 (7.97); 7.6668 (2.61); 7.6492 (6.95);

Physikalische Daten: ^] H-NMR, 6 [ppm] oder CAS- bzw .

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

phenyl 7.6482 (6.89); 7.6308 (5.47); 7.6035 (5.26); 7.5845 (6.41)

7.5657 (2.23); 7.4252 (7.63); 7.4065 (6.33); 7.3192 (1.51) 7.3026 (3.31); 7.2982 (3.24); 7.2816 (6.65); 7.2776 (2.71) 7.2649 (3.39); 7.2607 (4.16); 7.2441 (1.98); 7.0108 (0.97) 7.0064 (1.34); 6.9942 (8.76); 6.9861 (2.10); 6.9741 (14.69) 6.9624 (2.53); 6.9538 (8.60); 6.9411 (2.78); 6.9377 (2.71 ) 6.9273 (2.23); 5.4474 (0.58); 3.5774 (6.07); 3.5604 (15.77) 3.5437 (16.00); 3.5269 (6.84); 2.9691 (8.40); 2.9516 (15.43); 2.9342 (7.60); 2.1492 (24.45); 1.9642 (1.04) 1.9579 (1.58); 1.9523 (12.05); 1.9462 (22.63); 1.940C (31.46); 1.9338 (21.84); 1.9276 (1 1.33); 1.3724 (3.08) 1.2845 (0.43); 1.2761 (3.32); 0.0079 (0.68); -0.0002 (15.49); -0.0085 (0.64)

[CD3CN], Spektrometer: 399.95MH2 8.7335 (5.80); 8.7238 (5.79); 8.7218 (5.88); 7.8137 (5.32) 7.81 16 (5.51); 7.7942 (6.72); 7.7920 (6.81); 7.6526 (6.31) 7.6407 (6.26); 7.6330 (5.17); 7.6211 (4.91); 7.4201 (0.32) 7.3245 (1.51); 7.3079 (3.19); 7.3034 (3.16); 7.291 1 (2.10) 7.2869 (6.53); 7.2827 (2.58); 7.2702 (3.18); 7.2660 (4.06) 7.2572 (0.32); 7.2494 (1.92); 7.0307 (1.96); 7.0148 (2.24) 7.0103 (2.35); 6.9981 (8.83); 6.9899 (2.02); 6.9779 (14.13) 6.9666 (1.86); 6.9577 (7.50); 6.9452 (1.12); 6.9419 (0.91 ) 5.4484 (0.54); 3.5947 (6.03); 3.5777 (15.78); 3.5612 (16.00); 3.5443 (6.78); 2.9735 (8.07); 2.9560 (15.06) 2.9386 (7.33); 2.1548 (43.1 1); 2.1084 (0.35); 1.9652 (1.75) 1.9590 (2.35); 1.9533 (20.50); 1.9471 (38.61); 1.941C (54.32); 1.9348 (37.80); 1.9286 (19.73); 1.3722 (5.33)

2- (trifluormethyl)- 1.3405 (0.53); 1.2849 (0.79); 1.2764 (5.84); 0.0079 (0.93);

20-105 3- pyridyl 2,6-difluor-phenyl CH2 CH2 H 0.0002 (26.02); -0.0084 (1.10)

[DMSO], Spektrometer: 399,95MHz

8,4438 (3,31); 8,4226 (3,36); 7,473 (2,85); 7,4697 (3, 19) 7,4532 (6,8); 7,4505 (6,74); 7,4366 (3,01); 7,4323 (3, 14) 7,4187 (5,25); 7,4143 (4,95); 7,3994 (3,15); 7,3943 (3,52) 7,3905 (3,91); 7.3862 (3,45); 7,3719 (5,76); 7,3681 (5.89) 7,3537 (3,59); 7.3501 (4,32); 7,3293 (3,87); 7,3087 (2.56) 7,2915 (1 ,6); 7,2837 (5.55); 7,2804 (5,23); 7,2657 (4.18) 7,2616 (3,65); 7,1028 (1 ,1 1 ); 7,0912 (5,81); 7,0714 (8,95) 7,0518 (4,79); 7,0389 (0,9); 5,7605 (0,99); 4,3148 (0,84) 4,297 (1 ,97); 4,2789 (2,56); 4,2602 (2,03); 4,2429 (0,92) 3,3372 (17,93); 2,8941 (1 ,12); 2,8756 (1 ,22); 2,8607 (3,46) 2,8419 (3,76); 2,8325 (3,85); 2,8152 (3,53); 2,7988 (1 ,32) 2,7816 (1 ,1 1); 2,6717 (0,33); 2,5068 (34,02); 2,502« (42,22); 2,4984 (32,02): 1 , 1501 (15,98); 1 , 1333 (16)

20-106 2-chlor-phenyl 2,6-difluor-phenyl CH2 CH(CH3) H 0,0078 (1 ,03); -0,0002 (18,04); -0,0083 (1 ,14)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

[DMSO], Spektrometer: 399,95MHz

8,7305 (3,33); 8,7096 (3,35); 7,5201 (0,97); 7,5034 (2,25) 7,4995 (2,22); 7,4825 (3,92); 7,4657 (2,37); 7,4617 (2,41) 7,4449 (1 ,1); 7,3628 (0,87); 7,3457 (2,15); 7,3428 (2,13) 7,3253 (3,75); 7,3052 (2,51); 7,2878 (1 ,12); 7, 1488 (6,59) 7,1295 (9,71); 7,1093 (5,82); 7,1011 (1,8); 7,0869 (1 ,48) 7,0751 (5,92); 7,0556 (8,95); 7,0359 (4,91); 7,0234 (1 ,03) 5,7601 (2,65); 4,3197 (0,92); 4,3024 (2,06); 4,284 (2,66) 4,2661 (2,1 1); 4,248 (0,98); 3,3373 (23,33); 2,8796 (1,3) 2,8608 (1 ,5); 2,8463 (3,43); 2,8277 (3,47); 2,8091 (3,54) 2,7921 (3,46); 2,7757 (1 ,54); 2,7585 (1 ,29); 2,6726 (0,37) 2,5071 (44,36); 2,5031 (53, 12); 2,3302 (0,37); 1 , 1388 (16)

20-107 2,6-difluor-phenyl 2,6-difluor-phenyl CH2 CH(CH3) H 1 ,1221 (15,97); -0,0002 (18,67)

[DMSO], Spektrometer: 399,95MHz

8,5208 (3,59); 8,4996 (3,65); 7,7624 (4,49); 7,7427 (6,14) 7,7324 (2,47); 7,7129 (5,08); 7,6946 (3,49); 7,6427 (3,49) 7,6236 (4,61); 7,6046 (1 ,81); 7,3686 (5,46); 7,362 (3,24) 7,3499 (5,4); 7,3407 (4,33); 7,32 (2,65); 7,303 (1 ,1); 7,1 164 (0,89); 7, 1041 (5,75); 7,0846 (9,17); 7,0648 (4,99); 7,0525 (0,88); 4,2957 (0,84); 4,278 (1 ,97); 4,2595 (2,59); 4,2412 (2,06); 4,2234 (0,9); 3,3365 (23,98); 2,9012 (1 ,45); 2,8825 (1 ,53); 2,8677 (3,12); 2,8493 (3,06); 2,8145 (3,13); 2,7974

2-(trifluormethyl)- (3,18); 2,7813 (1 ,61); 2,764 (1 ,45); 2,6716 (0,38); 2,507

(41 ,43); 2,5027 (54,72); 2,4986 (44,59); 2,3294 (0,36)

20-108 phenyl 2,6-difluor-phenyl CH2 CH(CH3) H 1 ,1298 (15,95); 1, 1131 (16); 0,0078 (1 ,08); -0,0002 (21 ,01)

[DMSO], Spektrometer: 399,95MHz

8,6234 (3,3); 8,6023 (3,37); 8,4598 (4,87); 8,455 (5,07) 8,4478 (5,32); 8,443 (4,86); 7,7344 (4,7); 7,7296 (4,58) 7,7156 (5,76); 7,7108 (5,19); 7,5025 (5,18); 7,4904 (5,36) 7,4837 (4,79); 7,4716 (4,46); 7,3741 (0,9); 7,357 (2,17) 7,3537 (2,05); 7,3365 (3,79); 7,3193 (2,34); 7,3159 (2,45) 7,2991 (1 ,13); 7,1092 (1 ,04); 7,0976 (5,81); 7,0779 (8,83) 7,0581 (4,82); 7,0457 (1); 5,7609 (0,54); 4,3138 (0,86) 4,2962 (2); 4,2781 (2,6); 4,2597 (2,08); 4,2418 (0,97) 3,3388 (21 ,6); 2,9002 (1 ,04); 2,8817 (1 ,19); 2,8665 (3,63) 2,8459 (5,54); 2,8261 (3,67); 2,8097 (1 ,28); 2,7924 (1 ,04) 2,6726 (0,33); 2,5077 (34,68); 2,5035 (42,14); 2,4992 (31 ,64); 1,9904 (1 ,19); 1 ,1929 (0,55); 1 , 1751 (1 ,36); 1, 157S

20-109 2-chlor-3-pyridyl 2,6-difluor-phenyl CH2 CH(CH3) H (16); 1 ,1411 (15,75); -0,0002 (16,67)

[DMSO], Spektrometer: 399,95MHz

8,4395 (3,53); 8,4184 (3,56); 7,6307 (5,36); 7,6109 (6,18) 7,4354 (2,29); 7,4338 (2,27); 7,4172 (5,65); 7,3987 (4,23) 7,3688 (1 ,15); 7,353 (4,99); 7,3491 (5,69); 7,3307 (8,3) 7,3148 (4,44); 7,3109 (4,59); 7,294 (1 ,32); 7,2502 (5,27)

20-110 2-brom-phenyl 2,6-difluor-phenyl CH2 CH(CH3) H 7,2462 (5,1 1); 7,2316 (4,47); 7,2276 (4,15); 7,0958 (5,89)

Physikalische Daten: ¹ H-NMR, 6 |ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,0762 (9,01); 7,0566 (4,92); 7,0441 (1.03); 4.3013 (0,9) 4,2833 (2,06); 4,265 (2,67); 4,2466 (2.12); 4.2287 (0,96): 3,3372 (18, 16); 2,9056 (1 ,41); 2,8873 (1 ,61 ); 2.8722 (3,35). 2,854 (3,27); 2,8277 (3,35); 2,8104 (3,34); 2.7944 (1 ,63) 2,7769 (1 ,4); 2,5067 (32,26); 2,5027 (39,54); 1.1474 (16) 1 ,1306 (15,94); -0,0002 (15,19)

Verbindung Nr. 20-111, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5973 (3,2); 8,576 (3,25); 8,3188 (0,36); 7,6884 (2,21); 7,6764 (3,28); 7,6657 (4,13); 7,6282 (1,34); 7,6172 (8,13); 7,6098 (6,21); 7,6034 (6,2); 7,5945 (7,46); 7,585 (1,24); 7,4977 (3,39); 7,4873 (3,31); 7,4766 (2,47); 7,3596 (0,79); 7,3423 (1,9); 7,3392 (2); 7,3221 (3,57); 7,3017 (2,4); 7,2846 (1,02); 7,1282 (3,01); 7,0869 (0,89); 7,0747 (5,48); 7,0551 (8,69); 7,0354 (4,73); 7,0226 (0,77); 6,9892 (6,06); 6,8501 (3,12); 4,3556 (0,79); 4,3376 (1,84); 4,3194 (2,36); 4,3009 (1,88); 4,283 (0,86); 3,3304 (34,98); 2,8634 (8,06); 2,846 (7,36); 2,6755 (0,4); 2,6712 (0,49); 2,5065 (55,44);

2-(difluormethyl)- 2,5023 (71,8); 2,3293 (0,47); 1,3976 (12,9); 1,1985

20-1 1 1 phenyl 2,6-difluor-phenyl CH3 CH(CH3) H (16); 1,1817 (15,99); 0,0078 (1,15); -0,0002 (23,5)

Verbindung Nr. 20-112, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8325 (0,87); 8,8178 (1,69); 8,8033 (0,9); 8,1023 (1,34); 8,0984 (1,06); 8,09 (1,04); 8,086 (1,41); 7,7223 (1,18); 7,7152 (1,61); 7,7006 (2,28); 7,6506 (0,53); 7,6446 (0,83); 7,6331 (1,86); 7,6275 (3,21); 7,6194 (2,93); 7,6097 (4,61); 7,6056 (3,18); 7,5913 (3,22); 7,5752 (1,22); 7,5667 (0,65); 7,5366 (0,45); 7,522 (0,35); 7,5149 (0,44); 7,486 (0,47); 7,4748 (6,75); 7,4547 (9,17); 7,4334 (0,67); 7,4274 (0,63); 7,3851 (1,66); 7,3716 (0,35); 7,3652 (0,37); 7,3527 (0,38); 7,3482 (0,52); 7,3242 (0,44); 7,313 (3,05); 7,3064 (0,61); 7,2922 (3,62); 7,2834 (0,81); 7,2728 (2,28); 7,2649 (0,7); 7,2592 (0,56); 7,2461 (3,66); 7,1854 (0,62); 7,1068 (1,71); 6,5853 (1,45); 6,5813 (1,13); 6,5764 (0,72); 6,573 (1,11); 6,569 (1,46); 5,7589 (0,94); 3,5459 (0,35); 3,5364 (1,34); 3,5286 (1,12); 3,5198 (3,43); 3,5032 (3,47); 3,4868 (1,57); 3,3316 (13,6); 3,2503 (0,49); 3,1897 (2,92); 3,1722 (4,99); 3,1548 (2,38); 2,9932 (0,54); 2,9757 (0,98); 2,9579 (0,57);

2-(difluormethyl)- 2,9422 (16); 2,5114 (15,32); 2,5072 (30,14); 2,5028

20-1 12 henyl 2,6-dichlor-phenyl CH2 CH2 H (40,01); 2,4983 (30,7); 2,1225 (0,41); -0,0002 (0,43)

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ³ Patent-Nr.

Verbindung Nr. 20-113, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7424 [0,88); 8,7288 (1,6); 8,7153 (0,88); 8,3173 (3,76); 8,1014 (1,32); 8,0975 (1,05); 8,0891 (0,99); 8,0851 (1,38); 7,7112 (1,28); 7,7052 (1,59); 7,6892 (2,3); 7,6426 (0,58); 7,638 (0,81); 7,6241 (2,24); 7,619 (3,02); 7,6093 (3,32); 7,6009 (2,97); 7,5953 (2,23); 7,5806 (0,69); 7,5374 (2,14); 7,5215 (1,48); 7,5164 (1,2); 7,4506 (1,9); 7,4464 (1,44); 7,4334 (2,19); 7,4276 (2,49); 7,3716 (1,49); 7,3654 (1,79); 7,3535 (1,81); 7,3484 (2,73); 7,3227 (1,75); 7,3104 (0,73); 7,3057 (1,09); 7,292 (2,76); 7,2873 (2,75); 7,2833 (2,9); 7,276 (4,39); 7,2692 (2,01); 7,2649 (2,4); 7,2596 (1,95); 7,2464 (0,76); 7,2413 (0,6); 7,1836 (3,49); 7,0445 (1,75); 6,586 (1,49); 6,5821 (1,18); 6,5741 (1,46); 6,5697 (1,51); 3,5469 (1,43); 3,5297 (3,57); 3,5146 (3,61); 3,4975 (1,63); 3,351 (107,28); 3,3273 (3,1); 2,9934 (2,96); 2,9759 (5,64); 2,9584 (2,78); 2,942 (16);

2-(difluormethyl)- 2,5079 (21,11); 2,5034 (27,83); 2,499 (21,41); 2,1196

20-1 13 henyl 2-chlor-phenyl CH2 CH2 H (0,39); 2,1047 (1,11)

Verbindung Nr. 20-114, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7976 (2,67); 8,783 (5,05); 8,7685 (2,75); 8,3162 (4,96); 7,7232 (0,47); 7,7126 (4,28); 7,7062 (5,41); 7,6907 (7,95); 7,6445 (1,75); 7,6398 (2,6); 7,6259 (8,26); 7,621 (12,07); 7,6116 (11,86); 7,603 (11,71); 7,5834 (2,06); 7,5172 (7,18); 7,5023 (5,32); 7,4964 (4,42); 7,3681 (1,53); 7,351 (3,58); 7,3475 (3,58); 7,3304 (6,9); 7,3098 (4,64); 7,2988 (6,37); 7,2933 (2,83); 7,1598 (12,75); 7,1013 (1,33); 7,0886 (10,19); 7,069 (16); 7,0579 (2,39); 7,0492 (8,59); 7,0362 (1,3); 7,0207 (6,41); 3,4911 (4,3); 3,4746 (12,35); 3,4588 (13,1); 3,4425 (5,16); 3,3225 (60,57); 3,2986 (1,51); 2,9218 (7,97); 2,9049 (15,53); 2,888 (7,22); 2,675 (0,71); 2,6709 (0,98); 2,6665 (0,74); 2,506 (109,63); 2,5018 (142,43); 2,4975 (107,93); 2,3287 (0,95); 2,3244

2-(difluormethyl)- (0,73); 1,3979 (1,26); 0,0077 (1,95); -0,0002 (44,93); -

20-114 phenyl 2,6-difluor-phenyl CH2 CH2 H 0,0075 (2,55)

Verbindung Nr. 20-115, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6859 (2,4); 8,6722 (4,39); 8,6588 (2,52); 8,3157 (11,03); 7,7173 (4,29); 7,7069 (5,92); 7,6949 (7,51);

2-(difluormethyl)- 7,6504 (1,37); 7,6443 (2,52); 7,6322 (12,29); 7,6261

20-1 15 phenyl 2,6-difluor-phenyl CH2 CH2 CH2 H (9,65); 7,6203 (9,23); 7,6149 (8,98); 7,6093 (15,36);

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(0,53); 7,3205 (0,53); 7,3197 (0,5); 7,3189 (0,49); 7,318 (0,51); 7,3172 (0,5); 7,3164 (0,49); 7,3156 (0,49); 7,3148 (0,48); 7,314 (0,41); 7,3132 (0,4); 7,3123 (0,39); 7,3115 (0,4); 7,3094 (4,03); 7,3059 (1,7); 7,3042 (1,56); 7,3034 (1,47); 7,3026 (1,45); 7,3018 (1,42); 7,301 (1,43); 7,3001 (1,35); 7,2993 (1,37); 7,2985 (1,36); 7,2977 (1,24); 7,2969 (1,25); 7,296 (1,23); 7,2953 (1,23); 7,2944 (1,15); 7,2937 (1,08); 7,2928 (1,08); 7,292 (1,06); 7,2912 (1,02); 7,2903 (1,05); 7,2895 (1,13); 7,2887 (1,21); 7,2879 (1,17); 7,2871 (1,21); 7,2862 (1,24); 7,2854 (1,31); 7,2846 (1,36); 7,2838

(1.4) ; 7,283 (1,47); 7,2822 (1,53); 7,2814 (1,54); 7,2806 (1,56); 7,2797 (1,6); 7,2789 (1,64); 7,2781 (1,63); 7,2773 (1,73); 7,2764 (1,91); 7,2756 (1,99); 7,2748 (2,06); 7,274 (2,17); 7,2732 (2,42); 7,2723 (2,63); 7,2715 (3,05); 7,2707 (3,3); 7,2699 (3,71); 7,269 (4,36); 7,2682 (5,11); 7,2598 (427,96); 7,2472 (1,59); 7,2439

(1.05) ; 7,2423 (0,93); 7,2399 (0,71); 7,2382 (0,56); 7,2374 (0,51); 7,2358 (0,43); 7,235 (0,41); 7,2341 (0,36); 7,2333 (0,35); 7,2325 (0,33); 6,9959 (2,37); 6,5292 (0,32); 5,2988 (1,86); 5,2781 (0,33); 5,2691 (0,32); 4,9815 (0,33); 4,1339 (0,34); 3,4911 (0,55); 3,4204 (0,92); 3,2502 (16); 3,1874 (0,5); 3,0278 (0,52); 3,0155 (0,51); 2,1633 (0,38); 2,1548 (0,39); 2,0052 (0,61); 1,5868 (2,32); 1,5704 (2,48); 1,5363 (24,44); 1,4702 (0,96); 1,4528 (0,91); 1,2683 (0,49); 1,256 (0,79); 0,6284 (0,38); 0,5985 (0,58); 0,5747 (0,43); 0,5708 (0,43); 0,5483 (0,44); 0,4776 (0,38); 0,3062 (0,43); 0,2916 (0,5); 0,2816 (0,42); 0,1679 (0,33); 0,1462 (0,69); 0,0497 (0,93); 0,0174 (0,34); 0,0166 (0,4); 0,0159 (0,48); 0,015 (0,48); 0,0142 (0,49); 0,0134 (0,58); 0,0125 (0,72); 0,0117 (0,82); 0,0109 (1,01); 0,0101 (1,27); 0,0082 (3,77); 0,0069 (2,02); 0,006 (2,42); 0,0051 (3,06); 0.0000 (124.02)

Verbindung Nr. 20-118, Solvent: [CDC13], Spektrometer: 400.13MHz

7,665 (0,75); 7,6635 (0,7); 7,6455 (0,94); 7,644 (0,91); 7,5752 (0,81); 7,5734 (0,79); 7,5566 (0,7); 7,5546 (0,62); 7,5289 (0,42); 7,5268 (0,6); 7,525 (0,65); 7,5231 (0,54); 7,5186 (0,5); 7,5076 (0,72); 7,5059 (0,76); 7,5041 (0,64); 7,4726 (0,9); 7,4709 (0,94); 7,4539 (0,66); 7,4521 (0,71); 7,4295 (1,6); 7,4121 (2,32);

2-(trifluormethyl)- 7,4073 (3,86); 7,2922 (1,11); 7,2911 (1,18); 7,2857

20-1 I i henyl 2,4-dichlor-phenyl CH(OCH3) C(CH2CH2) H (1,04); 7,2747 (0,32); 7,2739 (0,39); 7,273 (0,49);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7,2715 (1); 7,27 [1,22); 7,2681 [0,92); 7,2673 [1,14); 7,2658 [1,98); 7,2648 (2,3); 7,2641 [2,59); 7,2598 (71,63); 7,2542 (1,71); 7,2533 [1,37); 7,2525 (1,12); 7,2516 [0,96); 7,2508 (0,87); 7,25 [0,77); 7,2492 (0,71); 7,2484 [0,63); 7,2476 (0,55); 7,2467 [0,48); 7,2459 (0,43); 7,2451 [0,41); 7,2442 (0,39); 7,2434 [0,35); 7,2426 (0,33); 6,9959 [0,41); 6 (0,68); 5,1563 [2,86); 3,2515 (16); 1,5413 [2,81); 1,1056 (0,35); 1,0955 [0,46); 1,0919 (0,57); 1,0762 [0,74); 1,0708 (0,5); 0,9468 [0,32); 0,9319 (0,45); 0,9262 [0,65); 0,9212 (0,93); 0,916 [0,74); 0,9119 (1,24); 0,9101 [1,26); 0,9034 (2,72); 0,893 [0,95); 0,8872 (0,6); 0,877 (0,34); 0,0082 (0,62); 0,0059 (0,33); 0,0051 (0,39)

Verbindung Nr. 20-119, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8718 (0,55); 8,8577 [1,06); 8,8435 (0,56); 7,5093 (0,65); 7,505 (0,65); 7,4882 [1,26); 7,4715 (0,67); 7,4672 [0,79); 7,452 (3,08); 7,4311 [5,06); 7,3741 (4,76); 7,353 [2,88); 7,1628 (0,37); 7,1551 [2,12); 7,1354 (2,94); 7,1153 [1,81); 7,1073 (0,35); 4,3805 [0,89); 4,365 (1,61); 4,3489 [0,96); 3,4537 (1); 3,4393 [1,44); 3,4371 (1,44); 3,4287 [1,87); 3,4227 (1,15); 3,4141 [0,98); 3,3216 (6,01); 3,1796 (16); 2,506

20-119 2,6-difluor-phenyl 4-chlor-phenyl CH(OCH3) CH2 H (15,91); 2,5015 (21,21); 2,4971 (16,22); -0,0002 (1,09)

Verbindung Nr. 20-120, Solvent: [CD3CN],

Spektrometer: 399.95MHz

8,413 (5,82); 8,4084 [6,01); 8,401 (6,05); 8,3964 [5,98); 7,7501 (6,22); 7,7454 [6,37); 7,7311 (6,93); 7,7265 [6,91); 7,3888 (6,67); 7,3767 [6,62); 7,3701 (6,22); 7,358 [5,91); 7,315 (1,48); 7,2981 (2,8); 7,294 (2,88); 7,2774 [5,64); 7,2605 (3,03); 7,2567 [3,53); 7,24 (1,7); 7,034 [1,71); 7,0019 (1,31); 6,9977 [1,48); 6,9847 (8,12); 6,9652 [12,79); 6,9535 (1,59); 6,9452 [6,91); 6,9321 (0,96); 5,447 [0,69); 3,6072 (5,51); 3,5905 (15,58); 3,574 (16); 3,5574 [6,09); 2,9864 (7,72); 2,9693 [14,57); 2,9521 (6,97); 2,1507 [45,69); 1,9711 (0,52); 1,9639 [1,18); 1,952 (12,63); 1,9459 [23,7); 1,9397 (33,17); 1,9337 [23,28); 1,9276 (12,36); 1,3715 [2,1); 1,3401 (0,39); 1,2844 [0,57); 1,2761 (2,18); -

20-120 2-chlor-3-pyridyl 2,6-difluor-phenyl CH2 CH2 H 0,0003 (0,35)

Verbindung Nr. 20-121, Solvent: [CD3CN],

Spektrometer: 399.95MHz

7,4155 (0,48); 7,3951 [3,94); 7,3889 (5,15); 7,3717

20-121 2,6-dichlor-phenyl 2,6-difluor-phenyl CH2 CH2 H (16); 7,3474 (6,9); 7,3318 (3,81); 7,3237 (2,35); 7,3081

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(2,31); 7,2916 (1,59); 7,2875 (1,66); 7,2708 (3,18); 7,254 (1,73); 7,2501 (2,03); 7,2335 (0,97); 6,9916 (1,52); 6,9879 (1,64); 6,975 (5,18); 6,9555 (7,6); 6,9354 (4,05); 6,9224 (0,7); 5,4464 (0,36); 3,631 (3,11); 3,614 (7,2); 3,596 (7,13); 3,5793 (3,44); 2,9879 (4,6); 2,9696 (8,01); 2,9517 (4,13); 2,1407 (13,38); 1,9635 (0,73); 1,9516 (7,7); 1,9454 (14,55); 1,9393 (20,39); 1,9331 (14,36); 1,927 (7,57); 1,3716 (2,51); 1,3401 (0,44); 1,2846 (0,57); 1,2762 (2,42)

Verbindung Nr. 20-122, Solvent: [CD3CN],

Spektrometer: 399.95MHz

7,5826 (5,72); 7,5783 (7,26); 7,5631 (7,35); 7,5596 (11,94); 7,541 (7,35); 7,5365 (5,83); 7,521 (5,42); 7,5169 (4,3); 7,4321 (6,15); 7,4132 (9,06); 7,3956 (3,52); 7,3945 (3,57); 7,3685 (6,23); 7,3479 (4,93); 7,3091 (1,48); 7,2924 (3,11); 7,2882 (3,25); 7,2716 (6,38); 7,2549 (3,28); 7,2508 (3,94); 7,2342 (1,88); 7,0112 (1,97); 6,993 (2,2); 6,9888 (2,27); 6,9761 (9,15); 6,9563 (14,31); 6,9448 (1,73); 6,9363 (7,65); 6,9233 (1,05); 3,5864 (6,21); 3,5695 (15,84); 3,5528 (16); 3,5359 (6,84); 2,9747 (8,49); 2,9571 (15,55); 2,9396 (7,56); 2,1449 (40,42); 2,1432 (39,69); 2,1074 (0,37); 1,9636 (2); 1,9518 (20,41); 1,9456 (37,73); 1,9395 (52,75); 1,9334 (36,61); 1,9273 (18,96); 1,3721 (2,9);

(trifluormethoxy)- 1,3406 (0,43); 1,2851 (0,6); 1,2766 (2,86); -0,0002

20-122 henyl 2,6-difluor-phenyl CH2 CH2 H (0,62)

Verbindung Nr. 20-123, Solvent: [CD3CN],

Spektrometer: 399.95MHz

9,0801 (4,37); 8,3734 (0,34); 8,0779 (0,54); 8,0564 (0,58); 8,0283 (0,48); 8,0072 (0,54); 7,8753 (4,87); 7,8569 (5,91); 7,7506 (2,67); 7,7315 (6,56); 7,7081 (10,99); 7,6858 (8,38); 7,6676 (7,41); 7,6491 (2,51); 7,5314 (0,33); 7,5109 (0,42); 7,4259 (0,8); 7,4202 (0,79); 7,2606 (1,35); 7,24 (3,01); 7,2227 (4,19); 7,2053 (2,67); 7,1852 (1,03); 7,1712 (0,56); 7,165 (0,52); 7,1499 (0,33); 6,8967 (1,05); 6,8841 (6,99); 6,8645 (11,28); 6,845 (5,98); 6,8315 (0,81); 6,3743 (1,52); 5,4473 (1,14); 4,0359 (5,9); 4,0191 (12,18); 4,0024 (6,7); 3,951 (0,72); 3,1122 (5,02); 3,0957 (9,47); 3,0791 (5,04); 3,0257 (0,63); 3,0155 (0,68); 2,4681 (0,9); 2,4632 (1,21); 2,4587 (0,82); 2,156 (225,3); 2,1503 (501,46); 2,1196 (2,74); 2,1135 (2,75); 2,1073 (2,81); 2,101 (1,96); 2,0948 (1,25); 1,9641 (12,84); 1,9521

20-123 2-cyano-phenyl 2,6-difluor-phenyl CH2 CH2 H (136,9); 1,946 (250,5); 1,9399 (342,39); 1,9337

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(240,09); 1,9275 (124,67); 1,7806 (0,92); 1,7744 (1,6); 1,7683 (2,15); 1,7621 (1,53); 1,7559 (0,86); 1,3716 (15,13); 1,3403 (2,55); 1,3132 (0,86); 1,2966 (1,15); 1,285 (3,95); 1,2766 (16); 1,2229 (0,42); 1,2167 (0,64); 1,2056 (0,55); 1,1883 (0,38); 1,1304 (0,35); 0,8817 (0,49); 0,8586 (0,52); 0,8409 (0,37); -0,0002 (2,32)

Verbindung Nr. 20-124, Solvent: [CD3CN],

Spektrometer: 399.95MHz

8,8469 (0,36); 8,8342 (0,37); 8,7487 (6,37); 8,7374 (6,53); 8,208 (6,64); 8,1879 (7,1); 7,8158 (1,77); 7,7015 (0,35); 7,6889 (0,34); 7,6833 (0,37); 7,6687 (0,45); 7,6521 (4,69); 7,6401 (4,76); 7,6319 (4,63); 7,6199 (4,35); 7,6044 (0,32); 7,4259 (0,77); 7,4199 (0,83); 7,3009 (1,46); 7,2843 (3,12); 7,28 (3,31); 7,2633 (6,63); 7,2467 (3,29); 7,2424 (4,38); 7,2361 (0,98); 7,226 (1,89); 7,1713 (0,55); 7,1651 (0,57); 7,1503 (0,37); 7,1441 (0,42); 6,9777 (0,84); 6,9734 (1,15); 6,9609 (8,33); 6,941 (14); 6,9296 (1,93); 6,9209 (7,55); 6,9083 (1,07); 6,3754 (0,56); 4,4849 (0,81); 4,4775 (0,5); 4,4734 (0,88); 4,4692 (0,55); 4,4618 (0,89); 3,7125 (0,88); 3,7054 (0,51); 3,7009 (0,91); 3,6968 (0,57); 3,6893 (0,85); 3,6246 (6,1); 3,6076 (15,27); 3,5901 (15,42); 3,5733 (6,87); 3,5288 (0,42); 3,5113 (1,22); 3,4937 (1,24); 3,4763 (0,43); 2,9902 (8,31); 2,9722 (15,03); 2,9548 (7,65); 2,4688 (0,34); 2,4641 (0,46); 2,4594 (0,36); 2,1646 (105,76); 2,1206 (0,4); 2,1142 (0,46); 2,1079 (0,52); 2,1018 (0,38); 1,9648 (2,06); 1,9585 (2,65); 1,9529 (23,35); 1,9467 (44,62); 1,9406 (63,49); 1,9344 (45,42); 1,9282 (24,55); 1,769 (0,41); 1,386 (0,4); 1,3718 (15,25); 1,3405 (2,6); 1,308 (0,65); 1,2915 (0,91); 1,2849 (3,44); 1,2764 (16); 1,2166

3 -(trifluormethyl)- (0,59); 1,1548 (1,33); 1,1373 (2,58); 1,1197 (1,36);

20-124 2-pyridyl 2,6-difluor-phenyl CH2 CH2 H 0,8805 (0,38); -0,0002 (0,46)

Verbindung Nr. 20-125, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4651 (3,06); 8,316 (0,52); 7,603 (3,12); 7,5985 (3,75); 7,5846 (5,99); 7,5799 (7,33); 7,5716 (0,67); 7,5652 (3,95); 7,5609 (4,16); 7,5508 (1,95); 7,5462 (1,77); 7,5375 (2,11); 7,5326 (4,05); 7,5298 (2,81); 7,5279 (2,67); 7,5254 (2,46); 7,5187 (3,11); 7,5147 (2,73); 7,5117 (4,45); 7,5069 (2,31); 7,4983 (2,53); 7,4936 (2,12); 7,3806 (15,87); 7,3767 (16); 7,3046 (5,11); 7,2935 (5,8); 7,291 (6,09); 7,2858 (4,11); 7,2836 (4,82);

20-125 2-fluor-phenyl 5-chlor-2-thienyl CH2 CH2 H 7,2803 (5,14); 7,2774 (6,68); 7,2746 (10,59); 7,2725

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L ³ Patent-Nr.

(8,3); 7,2594 (3,7); 7,2561 (9,16); 7,2536 (3,7); 6,9263 (11,37); 6,9249 (10,3); 6,9228 (11,38); 3,5151 (4,1); 3,4979 (10,57); 3,4832 (10,85); 3,4662 (4,73); 3,3217 (75,88); 3,0523 (0,4); 3,0357 (7,98); 3,0183 (15,2); 3,0015 (6,77); 2,6797 (0,34); 2,6751 (0,71); 2,6705 (0,98); 2,6659 (0,71); 2,6617 (0,32); 2,5239 (3,01); 2,5191 (4,59); 2,5105 (53,81); 2,506 (108,31); 2,5015 (142,01); 2,4968 (100,19); 2,4923 (46,53); 2,3327 (0,68); 2,3282 (0,94); 2,3236 (0,65); 1,2982 (0,41); 1,2586 (0,58); 0,146 (0,57); 0,016 (0,45); 0,008 (4,91); - 0,0002 (137,72); -0,0086 (4,08); -0,1497 (0,56)

Verbindung Nr. 20-126, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8955 (2,25); 8,8821 (4,07); 8,8684 (2,2); 8,3156 (0,5); 7,5431 (1,73); 7,5264 (3,66); 7,5218 (3,28); 7,5097 (2,34); 7,5052 (7,02); 7,5008 (2,44); 7,4885 (3,31); 7,4841 (4,09); 7,4675 (1,9); 7,3865 (15,76); 7,3826 (16); 7,1905 (1,42); 7,1874 (1,96); 7,1799 (11,48); 7,1604 (14,18); 7,1505 (1,68); 7,1398 (9,63); 7,1321 (1,61); 6,9192 (11,69); 6,9159 (11,67); 3,5099 (4,38); 3,4929 (11,66); 3,4784 (11,87); 3,4616 (4,98); 3,3205 (83,35); 3,0294 (0,41); 3,0138 (8,08); 2,9968 (15,71); 2,98 (6,98); 2,6792 (0,43); 2,6748 (0,93); 2,6702 (1,27); 2,6657 (0,92); 2,6611 (0,43); 2,5236 (4,01); 2,5187 (6,09); 2,5102 (72,3); 2,5057 (144,74); 2,5012 (189,52); 2,4966 (134,68); 2,492 (63,46); 2,3371 (0,43); 2,3325 (0,92); 2,3279 (1,26); 2,3234 (0,91); 2,3189 (0,42); 1,2586 (0,37); 0,1459 (0,72); 0,008 (6,22); -0,0002

20-126 2,6-difluor-phenyl 5-chlor-2-thienyl CH2 CH2 H (170,52); -0,0085 (5,32); -0,0172 (0,44); -0,1497 (0,71)

Verbindung Nr. 20-127, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4686 (1,65); 7,5309 (0,78); 7,5263 (0,92); 7,5176 (0,9); 7,5128 (1,83); 7,5081 (1,53); 7,5056 (1,32); 7,4988 (1,41); 7,4972 (1,4); 7,493 (2,29); 7,4868 (4,55); 7,4804 (2,02); 7,4705 (3,22); 7,4647 (16); 7,4503 (13); 7,4449 (5,08); 7,4294 (4,01); 7,3983 (0,56); 7,2636 (2,61); 7,2593 (3,08); 7,2571 (2,46); 7,2408 (5,44); 7,2383 (6,84); 7,2218 (1,95); 7,219 (3,16); 5,7555 (4,12); 4,0995 (0,69); 4,0844 (0,89); 4,0759 (1,15); 4,061 (1,27); 4,0522 (0,92); 4,0375 (0,88); 4,0283 (0,32); 3,9356 (0,88); 3,9219 (1,47); 3,9076 (0,96); 3,9018 (1,43); 3,8879 (2,15); 3,8739 (1,07); 3,7883 (1,25); 3,7723 (1,4); 3,7658 (1,22); 3,754 (1,15); 3,75

20-127 2-fluor-phenyl 4-chlor-phenyl CH(CF3) CH2 H (1,31); 3,7385 (0,92); 3,7319 (0,85); 3,7159 (0,74);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(34,17); -0,0057 (1)

Verbindung Nr. 20-139, Solvent: [DMSO], Spektrometer: 601.6MHz

8,5943 (1,48); 8,5852 (2,77); 8,576 (1,49); 7,4936 (3,73); 7,4923 (4,24); 7,481 (5,45); 7,4794 (7,34); 7,4495 (3,35); 7,4453 (3,61); 7,4385 (4,86); 7,4361

(2.27) ; 7,4344 (5,3); 7,4319 (2,17); 7,4254 (3,27); 7,4211 (3,83); 7,4117 (0,34); 7,4005 (2,03); 7,3984 (2,03); 7,3869 (16); 7,3843 (14,22); 7,3784 (9,11); 7,377 (7,58); 7,375 (12,27); 7,366 (1,98); 7,3624 (0,8); 6,9399 (7,99); 6,9386 (7,27); 6,9374 (8,35); 3,491 (3,18); 3,4796 (8,18); 3,47 (8,2); 3,4587 (3,58); 3,361 (0,38); 3,3539 (0,75); 3,3499 (1,21); 3,3448 (2,06); 3,3387 (3,67); 3,3258 (982,47); 3,3119 (2,08); 3,3029 (0,74); 3,2994 (0,74); 3,2953 (0,35); 3,2882 (0,33); 3,0243 (5,2); 3,0127 (10,5); 3,0019 (4,65); 2,6527 (1,58); 2,6189 (0,59); 2,616 (1,29); 2,6129 (1,8); 2,6098 (1,31); 2,6068 (0,58); 2,5648 (0,41); 2,5594 (0,69); 2,5535 (1,22); 2,5503 (1,52); 2,5489 (1,92); 2,5476

(2.28) ; 2,5447 (9,34); 2,5406 (521,84); 2,5354 (4,98); 2,529 (1,74); 2,5254 (1,2); 2,5223 (4,02); 2,5191 (5); 2,516 (4,81); 2,5073 (95,82); 2,5042 (206,37); 2,5012 (289,57); 2,4981 (210,67); 2,495 (99,49); 2,4241 (1,56); 2,3914 (0,58); 2,3884 (1,27); 2,3853 (1,76); 2,3823 (1,27); 2,3793 (0,58); 2,0734 (1,8); 0,0052 (0,44); -

20-139 2-chlor-phenyl 4-chlor-2-thienyl CH2 CH2 H 0,0002 (14,27); -0,0058 (0,47)

Verbindung Nr. 20-140, Solvent: [DMSO], Spektrometer: 601.6MHz

8,5884 (1,79); 8,5793 (3,33); 8,5701 (1,76); 7,6496 (6,04); 7,6489 (6,73); 7,6369 (6,22); 7,6354 (6,6); 7,4404 (3,17); 7,4386 (3,3); 7,432 (0,35); 7,428 (8,3); 7,4263 (6,15); 7,4156 (5,94); 7,4138 (5,8); 7,3877 (16); 7,3852 (15,99); 7,3649 (3,84); 7,3619 (6,28); 7,3523 (4,86); 7,3491 (10,4); 7,3458 (9,03); 7,3438 (5,04); 7,3392 (2,73); 7,3362 (5,13); 7,3338 (6,94); 7,3314 (4,4); 6,9495 (9,98); 6,9482 (8,47); 6,947 (10,1); 3,4858 (3,69); 3,4743 (9,46); 3,4647 (9,48); 3,4533 (4,11); 3,3642 (0,46); 3,3552 (0,52); 3,3524 (0,45); 3,3491 (1,1); 3,3473 (1,06); 3,3452 (1,17); 3,3424 (1,07); 3,3351 (9,18); 3,3333 (11,46); 3,3262 (963,66); 3,3144 (2,18); 3,3125 (2,53); 3,3065 (1,08); 3,3009 (0,67); 3,2921 (0,38); 3,027 (6,08); 3,0165 (11,65); 3,0155

20-140 2-brom-phenyl 4-chlor-2-thienyl CH2 CH2 H (12,05); 3,0048 (5,37); 2,6527 (1,7); 2,619 (0,56); 2,616

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw .

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(0,85); 2,6657 (0,67); 2,6613 (0,33); 2,5237 (2,87); 2,5189 (4,52); 2,5103 (48,99); 2,5058 (98,6); 2,5012 (129,12); 2,4966 (92,4); 2,4921 (43,72); 2,3326 (0,63); 2,328 (0,84); 2,3234 (0,62); 1,9886 (1,65); 1,2494 (0,32); 1,1924 (0,45); 1,1746 (0,9); 1,1568 (0,44); 0,008 (2,31); -0,0002 (64,37); -0,0085 (2,01)

Verbindung Nr. 20- 146, Solvent: [DMSO], Spektrometer: 399.95MHz

7,5029 (0,41); 7,4818 (0,63); 7,251 (0,43); 7,2301 (0,36); 4,0557 (1,33); 4,0379 (4,01); 4,0201 (4,04); 4,0023 (1,37); 3,3212 (5,03); 2,8109 (0,34); 2,5104 (3,74); 2,5061 (7,24); 2,5016 (9,33); 2,497 (6,65); 2,4926 (3,14); 1,9888 (16); 1,1927 (4,62); 1,1749

20-146 2-chlor-3-pyridyl 4-brom-phenyl CH2 CH2 H (8,89); 1,1571 (4,47); -0,0002 (4,26)

Verbindung Nr. 20-147, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6756 (1,7); 8,6619 (3,21); 8,6479 (1,68); 8,316 (0,33); 7,7034 (2,41); 7,6963 (3,06); 7,681 (4,49); 7,6377 (1,07); 7,6328 (1,57); 7,6191 (5,21); 7,614 (7,36); 7,6049 (7,49); 7,5962 (7,09); 7,5914 (3,99); 7,5772 (1,07); 7,5029 (5,14); 7,496 (15,25); 7,4911 (6,51); 7,48 (6,36); 7,4751 (16); 7,469 (2,04); 7,2948 (3,54); 7,2377 (1,85); 7,2315 (13,49); 7,2107 (11,61); 7,1557 (7,8); 7,0165 (3,86); 3,5014 (2,92); 3,484 (7,2); 3,4694 (7,25); 3,4521 (3,21); 3,3231 (116,28); 2,8336 (5,54); 2,8161 (10,87); 2,7985 (4,94); 2,6749 (0,73); 2,6704 (1,03); 2,6659 (0,75); 2,5237 (3,61); 2,5103 (56,57); 2,5059 (112,86); 2,5014 (148,07); 2,4968 (106,8); 2,4923 (51,39); 2,3327 (0,69); 2,3281 (0,94); 2,3236 (0,7);

2-(difluormethyl)- 1,2493 (0,35); 0,0079 (2,44); -0,0002 (65,07); -0,0085

20-147 phenyl 4-brom-phenyl CH2 CH2 H (2,23)

Verbindung Nr. 20-148, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3636 (2,28); 8,3165 (2,18); 7,564 (1,98); 7,5596 (2,52); 7,5456 (3,8); 7,5411 (5,24); 7,5319 (1,67); 7,5258 (2,72); 7,5224 (3,94); 7,5184 (3,19); 7,5008 (3,43); 7,4945 (14,44); 7,4901 (5,26); 7,4841 (2,61); 7,4786 (5,7); 7,4737 (16); 7,4675 (2,24); 7,2889 (3,68); 7,2789 (3,86); 7,2767 (4,01); 7,268 (3,6); 7,2605 (8,72); 7,2411 (7,36); 7,2309 (13,69); 7,2101 (11,71); 3,49 (2,73); 3,4726 (6,23); 3,4578 (6,33); 3,4401 (3,14); 3,3235 (46,76); 2,8262 (5,86); 2,8083 (10,62); 2,7905 (5,27); 2,6752 (0,46); 2,6705 (0,64); 2,6661 (0,49);

20-148 2-fluor-phenyl 4-brom-phenyl CH2 CH2 H 2,5237 (2,15); 2,5104 (36,73); 2,506 (73,71); 2,5015

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(97,24); 2,497 (71,37); 2,4926 (35,42); 2,3329 (0,45); 2,3282 (0,62); 2,3236 (0,46); 1,2492 (0,38); 0,008 (1,41); -0,0002 (39,4); -0,0084 (1,61)

Verbindung Nr. 20-149, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5882 (1,81); 8,5745 (3,45); 8,5606 (1,79); 7,7677 (4,21); 7,7485 (5,55); 7,7109 (1,79); 7,6936 (4,77); 7,675 (3,56); 7,6431 (3,51); 7,6242 (4,28); 7,6056 (1,64); 7,403 (6,18); 7,3962 (10,38); 7,3909 (4,34); 7,3804 (6,39); 7,3745 (16); 7,3679 (2,18); 7,3058 (10,21); 7,286 (6,51); 3,5028 (3,01); 3,4852 (6,81); 3,4707 (6,87); 3,4529 (3,31); 3,3227 (28,64); 2,8689 (5,7); 2,851 (10,59); 2,8332 (5,06); 2,6749 (0,55); 2,6705 (0,74); 2,6658 (0,51); 2,5238 (2,39); 2,5104 (41,04); 2,5059 (81,05); 2,5014 (105,24); 2,4967 (74,92); 2,4922 (35,14); 2,3327 (0,49); 2,3282 (0,68);

2-(trifluorniethyl)- (trifluormethoxy)- 2,3235 (0,51); 1,2492 (0,41); 0,008 (2,57); -0,0002 henyl henyl CH2 CH2 H (68,98); -0,0085 (2,04)

Verbindung Nr. 20-150, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3863 (0,42); 7,5561 (0,35); 7,5516 (0,48); 7,5371 (0,75); 7,533 (1,05); 7,5225 (0,35); 7,5179 (0,83); 7,5145 (0,89); 7,5034 (0,48); 7,4969 (0,54); 7,3907 (1,63); 7,3859 (0,64); 7,3742 (0,77); 7,369 (2,63); 7,3626 (0,39); 7,2983 (1,73); 7,2904 (0,83); 7,2783 (1,2); 7,2756 (1,46); 7,2728 (1,14); 7,2699 (0,73); 7,2638 (0,67); 7,2609 (0,69); 7,2562 (1,28); 7,2539 (1,04); 7,243 (0,48); 7,2402 (0,56); 7,2376 (0,69); 7,235 (0,46); 4,0557 (1,23); 4,0379 (3,73); 4,0201 (3,77); 4,0023 (1,27); 3,5122 (0,52); 3,4949 (1,11); 3,48 (1,08); 3,4621 (0,56); 3,3226 (18,63); 2,8865 (1,01); 2,8684 (1,76); 2,8506 (0,89); 2,524 (0,78); 2,5193 (1,24); 2,5107 (12,97); 2,5063 (25,98); 2,5017 (34,12); 2,4972 (24,58); 2,4927 (11,79); 1,9887 (16); 1,1926 (4,34);

(trifluormethoxy)- 1,1749 (8,55); 1,157 (4,22); 0,008 (0,55); -0,0002

20-150 2-fluor-phenyl henyl CH2 CH2 H (15,34); -0,0084 (0,5)

Verbindung Nr. 20-151, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5116 (1,7); 8,4979 (3,21); 8,4842 (1,69); 7,4806 (3,07); 7,4773 (3,81); 7,4608 (6,94); 7,4575 (7,58); 7,439 (3,52); 7,4345 (3,77); 7,4212 (5,67); 7,4166 (5,88); 7,4113 (1,49); 7,4039 (10,57); 7,397 (5,17);

(trifluormethoxy)- 7,3875 (4,6); 7,3822 (16); 7,3764 (4,96); 7,3615 (6,22);

20-151 2-chlor-phenyl phenyl CH2 CH2 H 7,3581 (6,3); 7,3436 (3,65); 7,3401 (3,42); 7,3172

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(7,16); 7,3127 (7,28); 7,3018 (10,26); 7,2991 (9,89); 7,2943 (5,04); 7,2821 (6,63); 3,5048 (3,22); 3,4872 (7,13); 3,4727 (7,23); 3,4551 (3,38); 3,3216 (55,25); 2,8855 (5,67); 2,8678 (10,91); 2,8501 (5,1); 2,6791 (0,48); 2,6748 (1); 2,6702 (1,31); 2,6657 (0,96); 2,6611 (0,45); 2,5235 (4,39); 2,5187 (6,84); 2,5102 (74,28); 2,5057 (147,7); 2,5011 (193,1); 2,4966 (138,18); 2,4921 (65,46); 2,337 (0,46); 2,3325 (0,95); 2,3279 (1,3); 2,3233 (0,94); 2,3187 (0,43); 1,2492 (0,41); 1,2354 (0,45); 0,146 (0,5); 0,017 (0,35); 0,008 (4,39); -0,0002 (121,24); -0,0085 (3,82); -0,1497 (0,49)

Verbindung Nr. 20-152, Solvent: [DMSO], Spektrometer: 399.95MHz 7,7103 (1,44); 7,4943 (0,45); 7,4909 (0,58); 7,486 (0,76); 7,4775 (0,86); 7,4715 (1,16); 7,4675 (1,55); 7,4602 (0,88); 7,454 (0,84); 7,4492 (0,86); 7,3439 (2,49); 7,3232 (3,56); 7,2521 (1,65); 7,2344 (1,84); 7,2201 (3,78); 7,1995 (2,86); 3,3305 (18,97); 3,1021 (5,24); 2,5054 (7,31); 2,5013 (10,06); 2,4971

20-152 2-fluor-phenyl 4-chlor-phenyl CH2 C(CH3)2 H (8,15); 1,2976 (16); -0,0002 (2,26)

Verbindung Nr. 20- 153, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8576 (1,52); 7,4679 (0,72); 7,4648 (0,81); 7,4479 (1,45); 7,4456 (1,53); 7,4217 (0,59); 7,4169 (0,63); 7,404 (1,07); 7,3991 (1,13); 7,3848 (0,74); 7,3754 (2,84); 7,3548 (4,49); 7,341 (0,89); 7,3377 (0,77); 7,3289 (1,6); 7,3242 (1,41); 7,3104 (0,76); 7,3054 (0,59); 7,2687 (3,31); 7,2477 (2,3); 3,3313 (33,5); 3,3264 (37,28); 3,1088 (4,84); 2,5235 (0,44); 2,5056 (19,52); 2,5013 (25,61); 2,4969 (19,68); 1,2881 (16);

20-153 2-chlor-phenyl 4-chlor-phenyl CH2 C(CH3)2 H 1,0424 (0,44); -0,0002 (6,24); -0,0084 (0,36)

Verbindung Nr. 20-154, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4373 (1,03); 8,4356 (1,11); 8,4341 (1,05); 8,4281 (1,03); 8,4265 (1,1); 8,4253 (1,12); 8,4236 (1,14); 8,0286 (1,82); 7,7718 (1); 7,7699 (1,07); 7,7556 (1,09); 7,7531 (1,19); 7,7512 (1,21); 7,4809 (1,03); 7,4797 (1,06); 7,4688 (1,06); 7,4676 (1,09); 7,4622 (1,04); 7,461 (1,03); 7,4502 (0,96); 7,4489 (0,96); 7,3843 (2,3); 7,3641 (3,3); 7,264 (3,21); 7,2436 (2,39); 3,3436 (38,07); 3,3355 (57,01); 3,1014 (5,14); 2,5016 (21,59); 1,9884 (1,16); 1,987 (1,19); 1,2918 (16); 1,191 (0,32); 1,1748 (0,62); 1,1732 (0,63); 1,1554 (0,33); -0,0002

20-154 2-chlor-3-pyridyl 4-chlor-phenyl CH2 C(CH3)2 H (3,58); -0,002 (3,59); -0,0033 (3,45)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

Verbindung Nr. 20-155, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8481 [1,63); 7,6241 [1,29); 7,6231 [1,28); 7,6045 [1,47); 7,4201 (0,5); 7,4182 [0,47); 7,4017 [1,37); 7,3997 [1,24); 7,3831 [3,37); 7,3622 [3,56); 7,3372 [0,72); 7,3328 [0,93); 7,3178 [0,96); 7,3134 [1,33); 7,2986 [1,95); 7,2944 [1,67); 7,2763 [4,19); 7,2554 (2,38); 3,3444 [31,89); 3,3338 (38,19); 3,1076 [4,93); 2,5054 (16,45); 2,5014 [20,87); 2,497 (15,85); 1,2898

20-155 2-brom-phenyl 4-chlor-phenyl CH2 C(CH3)2 H (16); 1,0424 (0,53); -0,0002 (4,72)

Verbindung Nr. 20-156, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8583 (1,78); 7,5892 (2); 7,5845 (2,14); 7,5487 [0,48); 7,5445 (0,65); 7,5268 [1,33); 7,5203 (0,49); 7,5132 [0,78); 7,5072 (1,03); 7,5001 [0,87); 7,4953 (0,64); 7,4863 [0,73); 7,4813 (0,86); 7,4661 [0,45); 7,4634 (0,39); 7,3852 (0,7); 7,3815 (0,65); 7,3644 [1,72); 7,3606 (1,75); 7,3367 [2,91); 7,3159 (1,22); 7,2725 [1,71); 7,2555 (2,12); 7,2496 [1,21); 7,2462 (1,27); 7,2445 [1,27); 7,2391 (0,88); 7,2368 [1,09); 7,2234 (0,91); 4,0393 [0,55); 4,0215 (0,56); 3,3351 [13,59); 3,2939 (5,9); 2,5038 [6,59); 1,9914 (2,19); 1,9898 [2,27); 1,3348 (16); 1,1956 [0,58); 1,1938 (0,61); 1,1778 [1,19); 1,1759 (1,27); 1,1601 [0,59); 1,1581

20-156 2-fluor-phenyl 4-chlor-phenyl CH2 C(CH3)2 H (0,62); 0,0019 (1,63); -0,0002 (1,7)

Verbindung Nr. 20-157, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0099 [1,75); 7,5959 (2,15); 7,4846 [0,73); 7,4669 (1,68); 7,4415 [0,55); 7,435 (0,75); 7,4231 [6,06); 7,4124 (1,21); 7,4 [3,27); 7,3941 (2,3); 7,3906 [1,87); 7,3784 (1,03); 3,342 [38,26); 3,3334 (54,14); 3,2976 (5,68); 2,5063 (17,39); 2,502 [23,82); 2,4977 (18,86);

20-157 2-chlor-phenyl 4-chlor-phenyl CH2 C(CH3)2 H 1,9886 (0,35); 1,3215 (16); -0,0002 (4,99)

Verbindung Nr. 20-158, Solvent: [DMSO], Spektrometer: 399.95MHz

7,9991 (1,77); 7,6403 [1,39); 7,6205 (1,57); 7,5971 [2,27); 7,4413 (5,56); 7,4389 [5,68); 7,4232 (1,45); 7,4068 [1,24); 7,4048 (1,28); 7,3866 [1,26); 7,3818 (1,95); 7,3678 [0,84); 7,3628 (0,76); 7,3557 [0,97); 7,3506 (0,75); 7,3362 [1,05); 7,3315 (0,94); 7,3182 (0,55); 7,3132 (0,5); 3,3316 [35,22); 3,298 (5,62); 2,506 [15,89); 2,5016 (21,92); 2,4972 [17,56); 1,9886 (0,72); 1,3242 (16); 1,1748 (0,38); -0,0002 [5,31); -0,0081

20-158 2-brom-phenyl 4-chlor-phenyl CH2 C(CH3)2 H (0,35)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

Verbindung Nr. 20-159, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4584 [1,13); 8,4537 [1,26); 8,4464 [1,26); 8,4417 (1,29); 8,1801 [1,84); 7,8674 [1,15); 7,8627 [1,23); 7,8487 [1,34); 7,844 [1,35); 7,6041 [1,87); 7,5992 (2,07); 7,5009 [1,28); 7,4888 (1,28); 7,4821 [1,26); 7,4701 (1,19); 7,4561 (0,59); 7,4511 [0,52); 7,4353 (1,85); 7,4302 [1,97); 7,417 (3,15); 7,3962 (0,93); 3,3257 (15,08); 3,2911 (5,49); 2,5059 (11,73); 2,5016 (15,94); 2,4974 [12,66); 1,9888 (0,74); 1,3274 (16);

20-159 2-chlor-3-pyridyl 4-chlor-phenyl CH2 C(CH3)2 H 1,1751 (0,4); 1,0116 [0,47); -0,0002 (3,3)

Verbindung Nr. 20- 160, Solvent: [DMSO], Spektrometer: 399.95MHz

7,8355 (1,24); 7,8289 (1,21); 7,6299 (1,78); 7,627 (3,23); 7,6241 (1,82); 7,5703 [0,52); 7,5654 (0,75); 7,5505 (1,1); 7,5464 (1,37); 7,5324 (0,7); 7,5277 (1,1); 7,5227 (0,4); 7,5139 (0,46); 7,5078 [0,87); 7,5041 (0,63); 7,5021 (0,58); 7,495 [0,82); 7,4933 (0,83); 7,4845 (7,2); 7,4816 (6,81); 7,4749 [0,77); 7,4703 (0,49); 7,2775 [2,52); 7,2603 (1,8); 7,258 [2,62); 7,2508 (1,16); 7,2419 [0,91); 7,2393 (0,88); 7,2301 (0,83); 5,3049 (5,71); 3,3224 [12,63); 3,1235 (16); 2,5247 (0,51); 2,5114 (8,21); 2,5069 [16,17); 2,5023 (21,38); 2,4977 (15,63); 2,4932 (7,47); 1,3348 [9,39); 1,2777

20-160 2-fluor-phenyl 2,4-dichlor-phenyl CH(OCH3) C(CH3)2 H (9,07); -0,0002 (2,38)

Verbindung Nr. 20-161, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0421 (2,11); 7,6406 [1,76); 7,6377 (3,23); 7,6347 (1,83); 7,4855 (6,92); 7,4825 (6,75); 7,4621 (1,33); 7,4591 (2,47); 7,4568 (1,51); 7,4365 (0,77); 7,4248 (1,43); 7,4139 (1,59); 7,406 (0,94); 7,3946 (1,29); 7,3808 (4,34); 7,3714 (2,5); 5,4002 [5,68); 3,3216 (25,14); 3,1227 (16); 2,524 [0,75); 2,5191 (1,19); 2,5106 (13,86); 2,5061 (27,65); 2,5015 [36,85); 2,4969 (27,09); 2,4924 (13,09); 1,3356 [1,03); 1,2979 (0,57); 1,2817 (9,39); 1,2738 [9,77); 1,2585 (0,72); 1,2492

20-161 2-chlor-phenyl 2,4-dichlor-phenyl CH(OCH3) C(CH3)2 H (1,29); -0,0002 (3,89)

Verbindung Nr. 20-162, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6021 [1,54); 8,5879 (2,98); 8,5738 [1,53); 7,9527 (1,91); 7,7555 [13,05); 7,7361 (4,13); 7,7308 (2,82); 7,6546 (2,87); 7,6516 [5,43); 7,6369 (2,18); 7,631

2-(trifluomiethyl)- (5,23); 7,5921 (4,65); 7,5724 [3,68); 7,4489 (1,72);

20-162 2-brom-phenyl 4-chlor-phenyl CH2 CH2 H 7,4461 (1,9); 7,43 (5,74); 7,4255 (2,8); 7,4119 (4,3);

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,409 (4,12); 7,3718 (2,51); 7,3671 (4,68); 7,3485 (12,06); 7,3315 (5,59); 7,3289 (5,83); 3,5052 (2,29); 3,488 (5,14); 3,472 (5,19); 3,4547 (2,81); 3,3799 (8,01); 3,0189 (3,28); 3,0012 (5,84); 2,9835 (2,86); 2,8906 (16); 2,7309 (12,91); 2,6754 (0,52); 2,671 (0,72); 2,6663 (0,53); 2,5243 (2,05); 2,5109 (39,29); 2,5064 (79,3); 2,5018 (105,67); 2,4973 (77,62); 2,4928 (37,69); 2,3331 (0,52); 2,3286 (0,7); 2,3241 (0,51); 1,4682 (0,5); 1,4606 (0,42); 0,9796 (0,46); 0,9661 (0,39); 0,9326 (0,36); 0,916 (0,74); 0,8983 (0,48); 0,008 (1,68); - 0,0002 (48,69); -0,0085 (1,63)

Verbindung Nr. 20-163, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8777 (2,65); 8,8635 (5,04); 8,8495 (2,6); 8,3166 (0,42); 7,9531 (0,68); 7,7574 (10,21); 7,7519 (13,11); 7,7286 (5,86); 7,7232 (4,18); 7,708 (7,88); 7,7023 (6); 7,6787 (0,73); 7,6734 (0,62); 7,5642 (10,01); 7,5426 (10,01); 7,5255 (4,47); 7,521 (4,11); 7,5088 (2,8); 7,5044 (7,75); 7,4999 (2,74); 7,4876 (3,72); 7,4832 (4,57); 7,4667 (2,12); 7,1869 (1,51); 7,1837 (2,09); 7,1763 (12,99); 7,1569 (16); 7,1503 (2,99); 7,1362 (10,71); 7,1285 (1,87); 3,5356 (4,02); 3,5184 (9,6); 3,503 (9,74); 3,4857 (4,43); 3,3242 (108,43); 3,0244 (1,42); 2,9948 (5,91); 2,9773 (10,81); 2,9597 (5,11); 2,9425 (0,46); 2,8909 (5,96); 2,8572 (1,01); 2,8179 (0,36); 2,7899 (1,12); 2,7792 (1,33); 2,7701 (0,74); 2,7589 (0,42); 2,7497 (0,36); 2,7312 (4,61); 2,6801 (0,44); 2,6758 (0,85); 2,6712 (1,14); 2,6666 (0,85); 2,662 (0,42); 2,5245 (3,68); 2,5197 (5,62); 2,5112 (61,16); 2,5067 (121,97); 2,5021 (160,91); 2,4975 (115,62); 2,4929 (54,08); 2,338 (0,35); 2,3334 (0,77);

2-(trifluormethyl)- 2,3288 (1,05); 2,3243 (0,75); 1,2338 (0,55); 0,0079

20-163 2,6-difluor-phenyl 4-chlor-phenyl CH2 CH2 H (2,67); -0,0002 (76,75); -0,0086 (2,21)

Verbindung Nr. 20-164, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5662 (2,01); 8,5521 (3,94); 8,5381 (2,02); 7,8837 (6,05); 7,8816 (6,49); 7,8639 (6,57); 7,8618 (6,63); 7,7587 (16); 7,7402 (5,25); 7,735 (3,51); 7,7142 (0,56); 7,7086 (0,88); 7,6991 (0,5); 7,6784 (0,54); 7,6037 (5,43); 7,5829 (4,14); 7,5421 (0,63); 7,5213 (0,46); 7,4578 (2,9); 7,4552 (3,03); 7,4391 (6,62); 7,4365 (6,78); 7,4204 (4,22); 7,4177 (4,18); 7,2879 (5,89);

2-(trifluormethyl)- 7,2839 (6,66); 7,269 (5,06); 7,265 (5,08); 7,1832 (3,66);

20-164 2-iod-phenyl 4-chlor-ptienyl CH2 CH2 H 7,179 (3,57); 7,1639 (5,46); 7,1599 (5,22); 7,1449

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(3,18); 7,1407 (2,95); 3,4938 (2,68); 3,4767 (6,03); 3,4606 (5,96); 3,4432 (2,98); 3,3236 (91,35); 3,0318 (4,18); 3,014 (7,2); 2,9946 (4,26); 2,8906 (0,44); 2,7874 (0,77); 2,7758 (0,95); 2,7631 (0,53); 2,7452 (0,34); 2,7371 (1,1); 2,7321 (0,5); 2,6753 (0,68); 2,6709 (0,91); 2,6663 (0,67); 2,524 (3,98); 2,5107 (50,53); 2,5063 (98,83); 2,5017 (129,88); 2,4972 (95,11); 2,4928 (45,91); 2,3331 (0,63); 2,3285 (0,85); 2,324 (0,62); 0,008 (2,02); -0,0002 (51,37); -0,0085 (1,62)

Verbindung Nr. 20-165, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4652 (3,88); 8,317 (0,92); 7,7512 (9,51); 7,7457 (13,96); 7,7339 (6,46); 7,7285 (3,65); 7,7132 (7,02); 7,7078 (5,49); 7,5917 (3,46); 7,5873 (4,21); 7,5734 (6,77); 7,5688 (8,6); 7,5576 (10,86); 7,5493 (5,39); 7,542 (3,5); 7,5369 (8,49); 7,5287 (4,99); 7,5259 (3,53); 7,5239 (3,28); 7,5215 (2,92); 7,5148 (3,85); 7,5132 (3,45); 7,5106 (3,27); 7,5079 (4,91); 7,503 (2,67); 7,4944 (2,91); 7,4898 (2,39); 7,2976 (5,87); 7,2883 (6,9); 7,2858 (6,6); 7,2785 (4,91); 7,2765 (5,64); 7,2728 (6,18); 7,2699 (16); 7,25 (11,9); 3,5358 (3,88); 3,5189 (9,41); 3,5029 (9,56); 3,4859 (4,39); 3,3248 (92,64); 3,0135 (5,94); 2,9959 (10,83); 2,9783 (5,15); 2,6763 (0,59); 2,6717 (0,83); 2,6672 (0,58); 2,5251 (2,6); 2,5203 (4,17); 2,5118 (46,72); 2,5072 (93,12); 2,5027 (122,56); 2,498 (88,07); 2,4935 (41,34); 2,334 (0,59); 2,3295 (0,82); 2,3249 (0,59); 1,3363 (2,16); 1,2587

2-(trifluormethyl)- (0,39); 1,2496 (2,69); 1,2339 (0,46); 1,188 (0,72); 0,008

20-165 2-fluor-phenyl 4-chlor-phenyl CH2 CH2 H (1,21); -0,0002 (34,4); -0,0086 (1)

Verbindung Nr. 20-166, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6068 (2,26); 8,5928 (4,34); 8,5788 (2,23); 7,7516 (16); 7,7296 (6,12); 7,7241 (4,32); 7,5839 (7,88); 7,5637 (6,3); 7,4971 (3,53); 7,496 (3,9); 7,4939 (4,71); 7,4779 (7,36); 7,4753 (12,02); 7,4731 (7,32); 7,4562 (4,48); 7,4488 (4,8); 7,4412 (6,52); 7,4338 (7,7); 7,4286 (1,95); 7,4222 (3,86); 7,414 (5,12); 7,4086 (2,48); 7,4049 (2,48); 7,3898 (10,12); 7,3865 (10,85); 7,382

(11.6) ; 7,381 (11,27); 7,3748 (15,28); 7,3724 (12,67); 7,3634 (1,81); 7,3561 (0,4); 5,757 (0,94); 3,5162 (3,36); 3,4991 (7,77); 3,4834 (7,84); 3,466 (3,77); 3,3252

(39.7) ; 3,0152 (4,91); 2,9976 (8,86); 2,9799 (4,23);

2-(trifluormethyl)- 2,6762 (0,36); 2,6716 (0,48); 2,667 (0,36); 2,5249

20-166 2-chlor-phenyl 4-chlor-phenyl CH2 CH2 H (1,53); 2,5201 (2,44); 2,5116 (27,58); 2,5071 (54,54);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

2,5025 [71,35); 2,4979 [51,08); 2,4933 [23,87); 2,3339 [0,32); 2,3293 [0,46); 1,3368 [0,72); 1,2497 [0,94); 0,008 [0,82); -0,0002 [24,28); -0,0085 [0,66)

Verbindung Nr. 20-167, Solvent: [DMSO], Spektrometer:

399.95MHz

8,7757 [2,13); 8,7616 [4,13); 8,7474 [2,09); 8,4739 [7,95); 8,4691 [8,53); 8,4619 [8,53); 8,457 [8,31); 8,3164 [0,34); 7,8536 [8,24); 7,8487 [8,46); 7,8348 [9,63); 7,8299 [8,99); 7,7572 (16); 7,7357 [5,69); 7,7303 (4); 7,5908 [7,22); 7,5707 [5,78); 7,509 [9,48); 7,4969 [9,14); 7,4902 [8,58); 7,4781 (8,5); 3,5304 (3,13); 3,5133 (7,18); 3,4976 [7,21); 3,4801 (3,49); 3,3233 [76,93); 3,3038 (0,53); 3,2858 [0,38); 3,018 (4,56); 3,0004 (8,2); 2,9826 (3,92); 2,6957 [1,43); 2,6759 (0,6); 2,6713 [0,82); 2,6667 (0,59); 2,5247 [2,61); 2,5199 (4,06); 2,5114 [44,89); 2,5068 (89,59); 2,5022 [118,23); 2,4976 (84,85); 2,4931 [39,51); 2,3336

2-(trifluormethyl)- (0,57); 2,329 [0,75); 2,3244 (0,53); 1,2496 [0,41);

1,2345 (0,37); 0,008 [1,19); -0,0002 (34,81); -0,0086

20-167 2-chlor-3-pyridyl 4-chlor-phenyl CH2 CH2 H Π,οη

20-168 2-chlor-3-pyridyl 2,4-dichlor-phenyl 0 CH2 CH(CH3) H

20-169 2-chlor-3-pyridyl 4-chlor-phenyl 0 CH2 CH(CH3) H

Verbindung Nr. 20-170, Solvent: [DMSO], Spektrometer:

399.95MHz

8,761 [2,56); 8,7414 (2,58); 8,4846 [4,68); 8,4798 (5,03); 8,4726 [5,03); 8,4677 (4,92); 7,8638 [4,71); 7,8589 (4,83); 7,845 [5,47); 7,8401 (5,13); 7,6517 [8,24); 7,646 (8,6); 7,6075 [6,44); 7,5859 (8,23); 7,5183 [5,37); 7,5063 (5,16); 7,4996 (4,9); 7,4875 (4,86); 7,4474 [5,35); 7,4417 (5,02); 7,4259 (4,2); 7,4202 (4,03); 4,1599 [0,72); 4,1431 (1,68); 4,1246 [2,01); 4,1072 (1,71); 4,0903 [0,75); 3,3329 (130,06); 3,2479 [1,64); 3,2305 (1,61); 3,2148 [3,57); 3,1974 (3,44); 3,1702 [3,53); 3,1539 (3,58); 3,137 [1,75); 3,1207 (1,59); 2,6719 [0,34); 2,5421 (44,66); 2,5252 [0,95); 2,5205 (1,52); 2,5119 [19,7); 2,5073 (39,77); 2,5027 [52,6); 2,4981 (37,84); 2,4936 [17,82); 2,3296 (0,34);

20-170 2-chlor-3-pyridyl 2,4-dichlor-phenyl s CH2 CH(CH3) H 1,2899 (16); 1,2732 (15,76); -0,0002 (5,97)

Verbindung Nr. 20-171, Solvent: [DMSO], Spektrometer:

399.95MHz

8,6948 (2,19); 8,675 (2,1); 8,4784 (4,47); 8,4735 [4,79);

20-171 2-chlor-3-pyridyl 4-chlor-phenyl s CH2 CH(CH3) H 8,4663 (4,78); 8,4615 (4,65); 7,829 (0,35); 7,8221

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

[4,51); 7,8172 [4,63); 7,8103 [0,49); 7,8033 [5,34); 7,7984 [4,94); 7,5031 [5,23); 7,4911 [5,09); 7,4878 [0,94); 7,4843 [4,98); 7,4723 [4,67); 7,453 [0,69); 7,447 [6,45); 7,4414 (2,4); 7,4307 [3,48); 7,425 (16); 7,4192 [2,38); 7,401 (2,37); 7,3953 [15,88); 7,3895 (3,36); 7,3788 [2,42); 7,3731 (6,08); 7,3671 [0,74); 7,3617 (0,6); 7,3431 [0,34); 4,1071 (0,73); 4,0904 [1,68); 4,0735 (1,91); 4,0711 [1,83); 4,0542 (1,65); 4,0373 [0,71); 3,338 (282); 3,3029 [0,42); 3,2056 (2,02); 3,196 [0,34); 3,1885 (2); 3,1721 [3,44); 3,155 (3,31); 3,0935 [3,44); 3,0771 (3,49); 3,06 [2,17); 3,0435 (2,01); 2,6762 [0,39); 2,6717 (0,54); 2,667 [0,37); 2,5419 (51,59); 2,5251 [1,63); 2,5203 (2,45); 2,5117 [30,83); 2,5072 (62,38); 2,5026 [82,24); 2,4979 (58,89); 2,4934 [27,56); 2,3338 (0,38); 2,3293 [0,52); 2,3247 (0,39); 1,2606 (1,19); 1,2492 (15,64); 1,2324 (15,4); -0,0002 (1,31)

Verbindung Nr. 20-172, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3453 (1,74); 8,3257 [1,75); 7,5999 (1,54); 7,5955 [1,87); 7,5816 (3,12); 7,5746 (8,3); 7,568 (7,86); 7,5621 [2,08); 7,5577 (1,97); 7,5479 (0,98); 7,5433 [0,88); 7,5346 (1,06); 7,5297 [2,01); 7,5268 (1,44); 7,525 [1,38); 7,5225 (1,18); 7,5157 [1,63); 7,5114 (1,51); 7,5089 [2,08); 7,504 (1,13); 7,4954 [1,24); 7,4908 (1,12); 7,3861 [3,63); 7,3796 (3,32); 7,3639 [4,91); 7,3575 (4,68); 7,2996 [2,54); 7,2907 (3,01); 7,2883 [2,79); 7,2784 (2,53); 7,2722 [7,29); 7,2522 (5,68); 7,2482 [7,98); 7,2259 (5,61); 4,4027 (0,6); 4,3864 (1,37); 4,3691 [1,77); 4,3514 (1,49); 4,3349 [0,68); 4,1324 (1,75); 4,1164 [1,64); 4,1081 (3,75); 4,0921 (3,33); 4,0749 (3,61); 4,06 [3,46); 4,0506 (1,86); 4,0357 [1,49); 3,3803 (0,37); 3,3689 [0,64); 3,3366 (269); 3,2973 [0,47); 2,6762 (0,41); 2,6716 [0,58); 2,667 (0,4); 2,5418 [10,48); 2,5249 (1,82); 2,5201 [2,91); 2,5116 (34,32); 2,5071 [67,98); 2,5025 (88,73); 2,4979 [63,5); 2,4934 (30,01); 2,3338 [0,41); 2,3292 (0,57); 2,3247

20-172 2-fluor-phenyl 2,4-dichlor-phenyl O CH2 CH(CH3) H (0,41); 1,2724 (16); 1,2555 (15,8); -0,0002 (7,4)

Verbindung Nr. 20-173, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3587 (1,62); 8,3396 [1,61); 7,5813 (1,43); 7,5768 [1,81); 7,5631 (2,72); 7,5584 [3,59); 7,5489 (0,41); 7,5437 [2,73); 7,5393 (2,88); 7,5307 [1,12); 7,5258 (2,03); 7,523 [1,37); 7,521 (1,24); 7,5186 [1,18); 7,5119

20-173 2-fluor-phenyl 4-chlor-phenyl O CH2 CH(CH3) H (1,6); 7,5104 (1,38); 7,5078 (1,26); 7,5049 (2,12);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,5001 [1,11); 7,4915 [1,26); 7,4869 [1,01); 7,3476 [0,87); 7,3386 [10,81); 7,333 [3,09); 7,3217 [3,32); 7,316 [12,36); 7,3071 [1,08); 7,2944 (2,5); 7,2845 [2,89); 7,282 [2,85); 7,2755 (2); 7,2734 [2,36); 7,2703 [2,49); 7,2657 [5,54); 7,2634 [3,87); 7,2494 [1,81); 7,2468 [5,25); 7,0155 (1,1); 7,0066 [12,04); 7,0009 (3,25); 6,9897 [3,06); 6,984 (10,46); 6,9751 [0,82); 4,3635 (0,55); 4,3473 [1,25); 4,33 (1,59); 4,3126 [1,33); 4,2962 (0,63); 4,0503 [2,17); 4,0345 (2,03); 4,0261 [3,45); 4,0102 (3,07); 3,9581 [3,29); 3,9436 (3,23); 3,9338 [2,23); 3,9194 (1,92); 3,3603 [0,38); 3,3296 (209,41); 3,3086 [0,54); 2,6755 (0,42); 2,6709 [0,59); 2,6663 (0,42); 2,5412 (13,76); 2,5243 [1,76); 2,5196 (2,67); 2,511 [33,94); 2,5064 (68,81); 2,5018 [91,1); 2,4972 (65,31); 2,4926 [30,57); 2,3332 (0,44); 2,3286 [0,6); 2,324 (0,43); 1,247 (16); 1,23 (15,85); 0,008 (0,44); -0,0002 (14,27); -0,0085 (0,41)

Verbindung Nr. 20-174, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4095 (1,97); 8,3904 [1,99); 7,6355 (8,69); 7,6298 [9,04); 7,5981 (6,41); 7,586 [1,74); 7,5814 (2,44); 7,5766 [8,37); 7,5678 (3,05); 7,5631 [4,04); 7,5531 (1,4); 7,5484 [2,83); 7,5441 (2,37); 7,5398 [1,33); 7,5348 (2,21); 7,5321 [1,58); 7,53 (1,45); 7,5277 [1,29); 7,5209 (1,83); 7,5168 [1,48); 7,514 (2,27); 7,5091 [1,19); 7,5005 (1,35); 7,496 [1,06); 7,4332 (5,46); 7,4275 [5,12); 7,4117 (4,32); 7,406 [4,13); 7,3025 (2,68); 7,2923 [3,14); 7,2898 (3,12); 7,2835 (2,3); 7,2815 (2,6); 7,2783 [2,78); 7,2734 (6,07); 7,2713 [4,39); 7,2572 (2,12); 7,2546 (5,5); 4,1974 (0,66); 4,1803 [1,54); 4,1626 (1,99); 4,145 [1,58); 4,1277 (0,69); 3,3275 [84,73); 3,2701 (1,92); 3,2522 [1,86); 3,237 (3,37); 3,2192 [3,23); 3,1637 (3,35); 3,1477 [3,41); 3,1306 (2,05); 3,1147 [1,89); 2,6713 (0,4); 2,5415 [4,13); 2,5246 (1,2); 2,5198 [1,91); 2,5112 (23,31); 2,5067 [46,67); 2,5021 (61,49); 2,4975 [44,11); 2,493 (20,79); 2,3289 (0,4); 1,2907 (16); 1,274 [15,82);

20-174 2-fluor-phenyl 2,4-dichlor-phenyl CH2 CH(CH3) H 0,008 (0,47); -0,0002 (14,67); -0,0086 (0,44)

Verbindung Nr. 20-175, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3401 (1,7); 8,3201 (1,6); 7,5667 (0,37); 7,5628 [0,46); 7,5565 (1,27); 7,5523 [2,14); 7,5466 (1,49); 7,5418 [1,02); 7,5383 (2,17); 7,5335 [5,23); 7,5279 (2,55);

20-175 2-fluor-phenyl 4-chlor-phenyl CH2 CH(CH3) H 7,5211 (1,62); 7,5189 (1,58); 7,5139 (4,14); 7,5076

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

[2,18); 7,5028 [1,08); 7,4942 (1,4); 7,4895 [0,91); 7,4642 [0,67); 7,4603 [0,34); 7,4439 [0,39); 7,4369 [0,73); 7,4309 [6,36); 7,4254 [2,38); 7,4146 [3,48); 7,409 [15,66); 7,403 [2,25); 7,3836 [2,34); 7,3777 [15,44); 7,372 (3,3); 7,3653 [0,55); 7,3613 (2,45); 7,3557 [6,04); 7,3499 (1,05); 7,3458 [0,92); 7,3267 (0,57); 7,3064 [0,32); 7,2949 (2,24); 7,2816 [3,06); 7,2791 (3,38); 7,2741 [2,55); 7,2704 (2,58); 7,2667 [2,28); 7,2627 (5,68); 7,2603 [4,07); 7,2495 (1,86); 7,2466 [1,94); 7,244 (2,97); 7,2415 [1,94); 7,2381 (0,5); 4,1477 [0,68); 4,1307 (1,51); 4,1129 (1,8); 4,0948 (1,49); 4,0775 [0,66); 3,3279 (269,64); 3,3039 (0,6); 3,2953 (0,36); 3,2219 [2,23); 3,2043 (2,12); 3,1884 [3,44); 3,1709 (3,32); 3,096 [3,55); 3,0798 (3,57); 3,0626 [2,29); 3,0463 (2,1); 2,68 [0,32); 2,6754 (0,68); 2,6708 (0,95); 2,6661 [0,68); 2,541 (11,82); 2,5241 [2,98); 2,5193 (4,61); 2,5108 [54,34); 2,5063 (109,41); 2,5017 [144,48); 2,497 (103,4); 2,4925 [48,5); 2,3331 (0,68); 2,3284 [0,94); 2,3238 (0,67); 1,2968 [0,88); 1,2801 (0,88); 1,2621 [1,44); 1,2502 (16); 1,2335 (15,83); 0,008 (0,89); -0,0002 (27,8); -0,0086 (0,81)

Verbindung Nr. 20-176, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8466 (2,46); 8,8275 [2,49); 7,5762 (7,9); 7,5698 (8,4); 7,5411 (0,88); 7,5338 [0,38); 7,5245 (1,83); 7,5199 [1,66); 7,5078 (1,31); 7,5033 (3,4); 7,499 (1,21); 7,4867 [1,65); 7,4822 (1,96); 7,4657 [0,93); 7,431 (0,34); 7,4091 [0,87); 7,3829 (3,9); 7,3765 [3,96); 7,3607 (5,18); 7,3543 [4,96); 7,2354 (7,89); 7,2131 [5,93); 7,1843 (0,66); 7,1812 [0,92); 7,1737 (5,68); 7,1545 [6,93); 7,1338 (4,76); 7,126 [0,79); 4,3688 (0,63); 4,353 [1,49); 4,3356 (1,94); 4,3179 [1,55); 4,3024 (0,72); 4,0626 [8,62); 4,0477 (7,8); 3,356 [0,46); 3,3276 (185,33); 2,6753 [0,47); 2,6707 (0,64); 2,6663 [0,46); 2,5411 (48,61); 2,524 (2,01); 2,5107 (36,77); 2,5062 (73,24); 2,5017 (96,47); 2,4971 [69,51); 2,4925 (33,12); 2,3329 [0,44); 2,3284 (0,62); 2,324 [0,44); 1,2633 (16); 1,2463 [15,96); 1,2338 (1,27); 0,008 [0,57); -0,0002

20-176 2,6-difluor-phenyl 2,4-dichlor-phenyl O CH2 CH(CH3) H (15,95); -0,0086 (0,48)

Verbindung Nr. 20-177, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8278 (2,13); 8,8082 [2,14); 7,5396 (0,81); 7,5229 [1,74); 7,5185 (1,47); 7,5062 [1,11); 7,5018 (3,23);

20-177 2,6-difluor-phenyl 4-chlor-phenyl O CH2 CH(CH3) H 7,4973 (1,13); 7,4852 (1,51); 7,4806 (1,9); 7,4641

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L- Patent-Nr.

(0,88); 7,3515 (0,89); 7,3425 (10,8); 7,337 (3,03); 7,3257 (3,28); 7,32 (11,85); 7,3111 (1,01); 7,1832 (0,65); 7,18 (0,85); 7,1724 (5,43); 7,1533 (6,55); 7,1324 (4,46); 7,1246 (0,71); 7,0022 (1,08); 6,9933 (11,85); 6,9877 (3,17); 6,9764 (3,04); 6,9707 (10,21); 6,9618 (0,79); 4,3443 (0,59); 4,3288 (1,34); 4,3117 (1,66); 4,2937 (1,27); 4,2781 (0,64); 3,9644 (9,63); 3,9498 (8,22); 3,3302 (369,65); 3,2885 (0,36); 2,6754 (0,68); 2,6708 (0,93); 2,6662 (0,66); 2,541 (38,14); 2,5242 (2,58); 2,5194 (4,22); 2,5109 (53,52); 2,5064 (107,51); 2,5017 (141,36); 2,4971 (100,74); 2,4926 (47,11); 2,3378 (0,33); 2,3332 (0,69); 2,3285 (0,92); 2,324 (0,66); 1,2328 (16); 1,2159 (15,73); 0,008 (0,75); - 0,0002 (23,53); -0,0086 (0,66)

Verbindung Nr. 20-178, Solvent: [DMSO], Spektrometer: 399.95MHz

8,894 (2,47); 8,8747 (2,49); 7,6468 (8,36); 7,6411 (8,67); 7,5852 (6,39); 7,5636 (8,46); 7,5547 (0,99); 7,5381 (1,92); 7,5334 (1,61); 7,5215 (1,27); 7,5169 (3,52); 7,5125 (1,24); 7,5002 (1,68); 7,4958 (2,11); 7,4792 (0,96); 7,4407 (5,6); 7,435 (5,23); 7,4192 (4,3); 7,4135 (4,09); 7,1979 (0,7); 7,1946 (0,97); 7,1873 (5,98); 7,1682 (7,1); 7,1473 (4,9); 7,1396 (0,83); 4,1645 (0,73); 4,1476 (1,68); 4,1297 (2,11); 4,1122 (1,74); 4,0952 (0,75); 3,3309 (33,07); 3,2137 (1,44); 3,1962 (1,41); 3,1807 (3,86); 3,1633 (3,76); 3,1504 (3,77); 3,1343 (3,79); 3,1174 (1,51); 3,1013 (1,37); 2,5424 (4,06); 2,5255 (0,56); 2,5207 (0,89); 2,5122 (10,31); 2,5077 (20,68); 2,5031 (27,29); 2,4984 (19,56); 2,4939

20-178 2,6-difluor-phenyl 2,4-dichlor-phenyl CH2 CH(CH3) H (9,16); 1,2784 (16); 1,2617 (15,76); -0,0002 (6,55)

Verbindung Nr. 20-179, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8309 (2,12); 8,8114 (2,04); 7,5502 (0,99); 7,5336 (1,83); 7,529 (1,48); 7,5169 (1,32); 7,5124 (3,32); 7,508 (1,15); 7,4957 (1,63); 7,4913 (1,95); 7,4745 (1,18); 7,4705 (0,44); 7,4412 (0,65); 7,4358 (5,1); 7,4299 (2,17); 7,4195 (3,29); 7,4136 (16); 7,4083 (2,75); 7,4012 (0,61); 7,3967 (2,75); 7,3913 (15,9); 7,3854 (3,2); 7,375 (2,21); 7,3692 (5,23); 7,3638 (0,64); 7,356 (0,59); 7,3537 (0,7); 7,3508 (0,47); 7,3387 (0,39); 7,193 (0,68); 7,1894 (1,07); 7,1822 (5,56); 7,1632 (6,58); 7,1615 (6,12); 7,1529 (0,84); 7,1486 (0,82); 7,1423 (4,63); 7,1345 (0,79); 4,1017 (0,75); 4,0848 (1,68);

20-179 2,6-difluor-phenyl 4-chlor-phenyl CH2 CH(CH3) H 4,0677 (1,94); 4,0661 (1,92); 4,0489 (1,65); 4,0319

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw .

Bsp.-Nr. X L ¹ Patent-Nr.

Verbindung Nr. 20-183, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5194 [0,64); 8,5054 (1,22); 8,4913 [0,65); 7,4933

[1.22) ; 7,4913 [1,22); 7,4734 [2,55); 7,4458 [1,06); 7,4417 [1,07); 7,4274 [1,65); 7,4235 [1,63); 7,4077 [0,84); 7,4035 [0,81); 7,3628 [1,07); 7,36 [0,97); 7,3441 [1,97); 7,3414 [1,77); 7,3256 [1,01); 7,323 [0,88); 7,2455 [2,02); 7,2416 (1,9); 7,2267 [1,52); 7,2227 (1,34); 7,198 (0,45); 7,1893 (4,17); 7,1843 [1,42); 7,1668 (4,56); 7,1575 (0,66); 6,7747 (0,54); 6,766 [4,48); 6,7433 (4); 6,7345 (0,5); 3,5066 (1,22); 3,4896 [3,1); 3,4737 (2,24); 3,4011 (1,23); 3,386 [2,64); 3,3705

(2.23) ; 3,3536 (1,1); 3,3279 (81,4); 2,9306 (16); 2,9068 (0,86); 2,5409 (10,1); 2,5058 (37,73); 2,5015 (47,42);

20-183 2-chlor-phenyl 4-chlor-phenyl N(CH3) CH2 CH2 H 2,4972 (34,79); -0,0002 (5,78)

Verbindung Nr. 20-184, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5071 (0,65); 8,4929 (1,17); 8,4791 (0,62); 7,65 [1,64); 7,6472 (1,53); 7,6308 (1,99); 7,6276 (1,83); 7,4043 [0,58); 7,4013 (0,63); 7,386 (1,7); 7,3828 (1,73); 7,3681 [1,7); 7,3642 (1,59); 7,3598 (1,5); 7,3545 (1,61); 7,3407 [1,61); 7,3356 (1,63); 7,3217 [0,66); 7,3168 (0,53); 7,2057 [1,94); 7,2008 (2,18); 7,1928 [4,48); 7,1877 (2,9); 7,1827 [1,86); 7,1755 (1,61); 7,1701 [4,72); 7,1612 (0,53); 6,7783 (0,5); 6,7695 (4,42); 6,752 [1,44); 6,7468 (3,99); 6,738 (0,43); 3,5083 (1,18); 3,4914 [2,98); 3,4751 (2,12); 3,395 (1,12); 3,3797 [2,38); 3,3641 (2,05); 3,3264 (101,83); 2,9342 (16); 2,6706 [0,4); 2,5409 (6,07); 2,5235 (1,54); 2,5103 (25,32); 2,506 (48,19); 2,5015 (62,01); 2,497 [45,67); 2,4928 (22,99); 2,3284 (0,41); 0,0078 (0,4); -0,0002 [9,06); -

20-184 2-brom-phenyl 4-chlor-phenyl N(CH3) CH2 CH2 H 0,0084 (0,4)

Verbindung Nr. 20-185, Solvent: [DMSO], Spektrometer: 399.95MHz

8,663 (1,62); 8,65 [2,84); 8,6358 (1,61); 8,3152 [0,41); 7,8103 (0,63); 7,797 [0,63); 7,4997 (2,88); 7,4802 [6,05); 7,4598 (2,02); 7,4526 [2,37); 7,4447 (2,65); 7,4378 [3,56); 7,4245 (1,58); 7,4176 [2,69); 7,4112 (2,09); 7,3976 [9,95); 7,3933 (8,41); 7,381 [3,34); 7,3618 (0,79); 7,3088 (0,43); 7,2888 (0,77); 7,2697 [0,58); 7,1821 (0,76); 7,1634 (6,5); 7,0708 (16); 7,0666 (14,38); 6,9773 (0,93); 6,9576 (0,96); 6,9384 [0,51); 4,1823 (4,58); 4,1685 (9,65); 4,1547 (5,01); 3,9765

20-185 2-chlor-phenyl 3,5-dichlorphenyl O CH2 CH2 H (0,37); 3,9633 (0,39); 3,6053 (2,57); 3,5911 [7); 3,5771

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(6,77); 3,5635 (2,36); 3,3246 (316,9); 3,2665 (0,51); 2,6709 (1,9); 2,541 (13,01); 2,5059 (246,36); 2,5019 (303,3); 2,4006 (0,45); 2,3285 (2,02); 1,2776 (1,6); 1,2602 (1,61); 1,2366 (0,46); -0,0002 (39,02)

Verbindung Nr. 20-186, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4502 (2,74); 8,4297 (2,75); 7,5527 (1,77); 7,5333 (3,93); 7,5134 (2,54); 7,4987 (2,98); 7,4783 (6,26); 7,4666 (0,79); 7,4637 (0,77); 7,453 (1,97); 7,4448 (2,42); 7,4388 (2,78); 7,4305 (3,34); 7,4243 (1,53); 7,4201 (1,83); 7,4107 (2,26); 7,402 (1,57); 7,3832 (6,13); 7,38 (7,2); 7,3778 (7,04); 7,3692 (8,3); 7,3592

(1.11) ; 7,3464 (0,63); 7,343 (0,67); 7,3359 (0,91); 7,3024 (5,18); 7,2951 (3,65); 7,2841 (4,07); 7,2683 (5,65); 4,2071 (0,7); 4,1946 (1,05); 4,1859 (1,43); 4,1731 (1,6); 4,1626 (1,09); 4,1509 (0,85); 4,1381 (0,46); 4,0941 (10,04); 4,0796 (6,82); 3,3261 (89,96); 2,6757 (0,45); 2,6711 (0,59); 2,6665 (0,39); 2,5412 (23,18); 2,5064 (72,37); 2,502 (88,19); 2,4976 (62,74); 2,4595 (0,34); 2,3331 (0,46); 2,3286 (0,57); 2,3245 (0,4); 1,7801 (0,34); 1,7615 (0,9); 1,7491 (1,12); 1,743 (1,06); 1,7301 (1,5); 1,7274 (1,49); 1,7151 (1,35); 1,7085 (1,35); 1,6965 (1,17); 1,6899 (0,56); 1,6778 (0,38); 1,6066 (0,33); 1,5881 (1,17); 1,5694 (1,6); 1,5534 (1,32); 1,5479 (1,42); 1,535 (1,16); 1,5314

(1.12) ; 1,5135 (0,83); 1,0047 (7,61); 0,9862 (16);

3 -(trifluormethyl)- 0,9679 (7,15); 0,9521 (0,77); 0,0078 (0,89); -0,0002

20-186 2-chlor-phenyl henyl O CH2 CH(CH2CH3) H (15,13); -0,0084 (0,59)

Verbindung Nr. 20-187, Solvent: [DMSO], Spektrometer: 399.95MHz

12,9515 (7,81); 12,8762 (0,37); 7,7979 (0,34); 7,6668 (4,85); 7,6634 (5,04); 7,6481 (5,98); 7,6444 (5,97); 7,6243 (0,32); 7,6117 (0,54); 7,6043 (0,63); 7,5893 (4,26); 7,5819 (16); 7,573 (9,12); 7,5696 (9,04); 7,5639 (5,41); 7,5597 (5,28); 7,5548 (7,03); 7,5527 (7,5); 7,546 (12,17); 7,5436 (11,07); 7,526 (2,67); 7,5219 (2,54); 7,5138 (6,51); 7,5116 (5,98); 7,5012 (6,97); 7,4989

(6.12) ; 7,4808 (4,16); 7,477 (3,84); 7,4624 (5,5); 7,4589

(5.13) ; 7,4443 (2,41); 7,4406 (2,13); 7,1268 (6,02); 7,1176 (6,29); 7,1143 (6,13); 7,1051 (5,43); 3,3238 (35,51); 3,0765 (1,4); 2,6756 (0,43); 2,6713 (0,58); 2,6668 (0,43); 2,5065 (66,1); 2,5022 (83,42); 2,4978 (60,82); 2,3332 (0,42); 2,3291 (0,55); 2,3246 (0,4);

20-187 2-fluor-phenyl 3,5-dichlorphenyl O CH2 CH2 H 1,3185 (0,48); 1,106 (4,47); 0,007 (3,34); -0,0002

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(60,47); -0,0083 (2,59)

Verbindung Nr. 20-188, Solvent: [DMSO], Spektrometer: 399.95MHz-.8,3163 (0,38); 8,3016 (2,08); 8,2813

(2.12) ; 7,5666 (1,4); 7,5623 (1,76); 7,5439 (5,17); 7,5364 (1,55); 7,5247 (6,51); 7,5047 (4,19); 7,4973 (1,6); 7,4882 (1,52); 7,4837 (1,38); 7,3332 (0,74); 7,2968 (6,56); 7,2892 (3,86); 7,28 (6,43); 7,2684 (10,33); 7,2637 (10,32); 7,2505 (2,72); 7,2478 (2,79); 7,245 (2,96); 4,2377 (0,67); 4,2244 (0,93); 4,2167 (1,36); 4,2034 (1,49); 4,1954 (0,99); 4,1898 (0,87); 4,182 (0,8); 4,1687 (0,39); 4,1426 (1,6); 4,1272 (1,08); 4,1182 (3,91); 4,1028 (3,34); 4,0961 (4,02); 4,082 (3,2); 4,0715 (1,53); 4,0574 (1,05); 3,3269 (97,68); 2,6758 (0,36); 2,6714 (0,49); 2,667 (0,35); 2,5418 (11,24); 2,511 (31,46); 2,5068 (59,34); 2,5024 (75,97); 2,4979 (55,71); 2,4936 (27,92); 2,3337 (0,37); 2,3291 (0,49); 2,3246 (0,35); 1,7714 (0,8); 1,759 (1,01); 1,7529 (1,09); 1,7375 (1,51); 1,7248 (1,32); 1,7187 (1,33); 1,7063

(1.13) ; 1,688 (0,39); 1,6319 (0,41); 1,6134 (1,16); 1,5947 (1,51); 1,5786 (1,18); 1,573 (1,38); 1,5602

3 -(trifluormethyl)- (1,03); 1,5571 (1,06); 1,5385 (0,79); 0,9806 (7,65);

0,9621 (16); 0,9436 (6,89); 0,0079 (0,66); -0,0002

20-1 ! 2-fluor-phenyl henyl O CH2 CH(CH2CH3) H (14,38); -0,0084 (0,61)

Verbindung Nr. 20-189, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7583 (1,18); 8,744 (2,29); 8,7298 (1,2); 7,5192 (0,84); 7,5026 (1,81); 7,498 (1,63); 7,4859 (1,17); 7,4814 (3,41); 7,4771 (1,35); 7,4647 (1,61); 7,4603 (2,05); 7,4437 (0,91); 7,3713 (0,77); 7,3653 (6,93); 7,3604 (2,74); 7,3492 (3,4); 7,344 (14,21); 7,3383 (2,27); 7,3052 (1,95); 7,2995 (12,79); 7,2945 (3,58); 7,283 (2,45); 7,2782 (6,59); 7,1633 (0,62); 7,1601 (0,9); 7,1525 (5,58); 7,1333 (6,75); 7,1126 (4,67); 7,1046 (0,83); 3,4105 (0,37); 3,3989 (4,49); 3,3838 (5,77); 3,3808 (6,27); 3,366 (5,46); 3,3357 (253,14); 3,0333 (1,28); 3,0155 (2,48); 2,9977 (2,4); 2,9799 (1,12); 2,6755 (0,4); 2,671 (0,51); 2,6665 (0,39); 2,5414 (34,24); 2,5244 (1,57); 2,5197 (2,34); 2,511 (28,7); 2,5066 (59,24); 2,502 (79,45); 2,4974 (59,12); 2,4928 (29,56); 2,3334 (0,36); 2,3287 (0,51); 2,3242 (0,38);

20-189 2-fluor-phenyl 4-chlor-phenyl CH(CH3) CH2 H 1,232 (16); 1,2145 (15,69); -0,0002 (3,72)

Verbindung Nr. 20-190, Solvent: [DMSO], Spektrometer:

20-190 2-fluor-phenyl 2,4-dichlor-phenyl CH(CH3) CH2 H 399.95MHz

Physikalische Daten: Ή-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(1,44); 7,4884 (1,14); 7,4839 (3,12); 7,4795 (1,17); 7,4672 (1,53); 7,4627 (1,88); 7,4462 (0,85); 7,3813 (0,36); 7,3623 (16); 7,3377 (0,56); 7,2682 (0,45); 7,2628 (0,47); 7,2475 (0,39); 7,2423 (0,41); 7,1654 (0,97); 7,1611 (0,82); 7,1535 (5,25); 7,1466 (1,26); 7,1344 (6,25); 7,1137 (4,4); 7,1056 (0,79); 4,3283 (0,48); 4,3072 (1,11); 4,291 (1,41); 4,2759 (1,08); 4,2549 (0,52); 3,4986 (0,72); 3,4839 (0,68); 3,4673 (0,35); 3,4055 (0,38); 3,3366 (877,92); 2,9191 (1,16); 2,9048 (1,32); 2,8845 (3,52); 2,8702 (3,3); 2,8587 (3,44); 2,8374 (3,39); 2,824 (2,11); 2,8028 (1,34); 2,6803 (0,61); 2,6758 (1,19); 2,6713 (1,63); 2,6667 (1,18); 2,6621 (0,59); 2,5415 (5,09); 2,5246 (5,17); 2,5198 (8,13); 2,5113 (89,76); 2,5068 (179,12); 2,5022 (235,98); 2,4976 (169,29); 2,4931 (79,58); 2,338 (0,52); 2,3335 (1,1); 2,3289 (1,52); 2,3243 (1,08); 2,3198 (0,48); 1,2348 (1,01); 1,1834 (14,03); 1,1668 (13,75); 1,1465 (0,43); -0,0002 (5,81)

Verbindung Nr. 20- 193, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7765 (1,98); 8,763 (3,72); 8,7494 (1,98); 7,5574 (13,39); 7,5471 (0,57); 7,5368 (16); 7,5305 (11,92); 7,5256 (11,89); 7,5123 (3,38); 7,5076 (2,9); 7,4956 (2,09); 7,4912 (6,3); 7,4867 (2,22); 7,4744 (2,89); 7,47 (3,73); 7,4534 (1,7); 7,2683 (6,59); 7,2631 (6,37); 7,2477 (5,72); 7,2425 (5,57); 7,177 (1,14); 7,1737 (1,63); 7,1661 (10,43); 7,1525 (2,16); 7,1469 (12,48); 7,14 (2,17); 7,1368 (1,44); 7,1261 (8,7); 7,1183 (1,4); 3,5159 (3,79); 3,4991 (9,67); 3,4845 (9,83); 3,4678 (4,1); 3,4058 (0,41); 3,3848 (0,79); 3,3376 (649,05); 2,8411 (7,03); 2,8242 (14,08); 2,8073 (6,32); 2,6803 (0,43); 2,676 (0,89); 2,6714 (1,15); 2,6667 (0,83); 2,6621 (0,52); 2,5416 (3,4); 2,5247 (3,39); 2,5199 (5,19); 2,5114 (63,6); 2,5069 (128,59); 2,5023 (170,29); 2,4976 (122,24); 2,4931 (57,37); 2,3383 (0,36); 2,3336 (0,78); 2,3291 (1,09); 2,3244 (0,77); 2,32 (0,34); -

20-193 2-fluor-phenyl 3,4-dichlorphenyl CH2 CH2 H 0,0002 (4,11)

Verbindung Nr. 20- 194, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2773 (1,89); 8,2562 (1,99); 7,5767 (5,78); 7,5725 (5,77); 7,5194 (0,83); 7,5147 (1,02); 7,5062 (0,93); 7,5013 (2,07); 7,4965 (1,55); 7,4939 (1,45); 7,4833 (1,61); 7,4803 (2,29); 7,4755 (1,45); 7,467 (1,19);

20-194 2-fluor-phenyl 2,4-dichlor-phenyl CH(CH3) CH2 H 7,4623 (1,37); 7,4538 (1,74); 7,4492 (1,73); 7,4353

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

(3,34); 7,4307 (3,23); 7,4161 (2,55); 7,4117 (2,02); 7,3901 (1,28); 7,3696 (10,68); 7,367 (11,34); 7,3623 (8,54); 7,3462 (1); 7,3417 (1,3); 7,2712 (2,69); 7,2599 (3,13); 7,2574 (3,35); 7,2502 (2,57); 7,2473 (2,84); 7,2445 (3,33); 7,2409 (5,41); 7,2264 (2,03); 7,2226 (4,08); 7,2198 (2,09); 4,3474 (0,53); 4,3267 (1,18); 4,3102 (1,52); 4,2945 (1,14); 4,2733 (0,53); 3,4746 (0,37); 3,4364 (0,48); 3,3364 (3083,87); 3,2046 (0,54); 2,9493 (1,2); 2,9348 (1,42); 2,915 (4,14); 2,9005 (4,25); 2,8959 (4,38); 2,8746 (3,73); 2,8616 (1,23); 2,8403 (1,27); 2,6803 (1,84); 2,6758 (3,74); 2,6711 (5,11); 2,6665 (3,66); 2,662 (1,76); 2,5414 (12,65); 2,5245 (15,39); 2,5198 (23,63); 2,5112 (279,98); 2,5067 (566,47); 2,5021 (750,44); 2,4974 (537,35); 2,4929 (250,69); 2,3379 (1,64); 2,3334 (3,56); 2,3288 (4,9); 2,3242 (3,45); 2,3197 (1,54); 1,2979 (0,32); 1,2583 (0,49); 1,235 (0,8); 1,1986 (16); 1,182 (15,78); 1,1473 (0,61); 0,008 (0,68); -0,0001 (20,86); -0,0085 (0,51)

Verbindung Nr. 20-195, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8112 (1,94); 8,7976 (3,61); 8,7839 (1,94); 8,3161 (0,51); 7,5293 (1,2); 7,5126 (2,6); 7,5081 (2,45); 7,4956 (1,88); 7,4914 (4,98); 7,4873 (1,96); 7,4747 (2,58); 7,4704 (2,97); 7,4537 (1,37); 7,3931 (10,46); 7,3715 (16); 7,3652 (2,33); 7,2927 (10,9); 7,2726 (7,31); 7,1739 (1,17); 7,1709 (1,54); 7,1633 (8,36); 7,1437 (10,97); 7,1234 (7); 7,1156 (1,26); 3,5131 (3,26); 3,4957 (7,89); 3,4811 (7,96); 3,4637 (3,52); 3,3237 (64,61); 2,869 (6,23); 2,8513 (12,02); 2,8337 (5,55); 2,6751 (0,52); 2,6706 (0,69); 2,6665 (0,48); 2,5235

4- (2,41); 2,5103 (36,06); 2,5061 (69,47); 2,5016 (90,6);

2,4971 (66,54); 2,4928 (32,92); 2,333 (0,44); 2,3283

(trifluormethoxy)- (0,59); 2,3239 (0,43); 0,0078 (1,05); -0,0002 (24,02); -

20-195 2,6-difluor-phenyl henyl CH2 CH2 H 0,0084 (0,89)

Verbindung Nr. 20-196, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6926 (1,79); 8,6788 (3,42); 8,6651 (1,78); 8,3172 (0,32); 7,701 (2,57); 7,6957 (3,4); 7,679 (4,78); 7,6348 (1,42); 7,6305 (1,84); 7,6163 (5); 7,6119 (5,03); 7,6069 (3,35); 7,6002 (7,95); 7,5934 (4,42); 7,5884 (3,93); 7,5861 (3,99); 7,57 (1,32); 7,4948 (4,24); 7,4922 (4,05); 7,4884 (2,58); 7,4781 (3,25); 7,4737 (2,64); 7,3976

2-(difluormethyl)- (trifluormethoxy)- (1,08); 7,3908 (10,07); 7,3859 (3,71); 7,3743 (4,46);

20-196 henyl henyl CH2 CH2 H 7,3692 (16); 7,3626 (2,14); 7,2985 (10,22); 7,2786

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

[0,35); 1,1753 (0,38)

Verbindung Nr. 20-199, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5053 (3,04); 8,4917 (5,76); 8,4778 (3); 7,7963 (11,33); 7,776 (12,76); 7,649 (14,08); 7,6366 (9,48); 7,6343 (9,54); 7,6169 (10,81); 7,6143 (10,59); 7,4723 (7,45); 7,4521 (6,58); 7,4292 (3,88); 7,4263 (4,21); 7,4107 (10,46); 7,4077 (10,67); 7,3921 (8,46); 7,3891 (7,81); 7,3562 (6,57); 7,3515 (8,21); 7,3365 (7,91); 7,3319 (9,57); 7,3177 (4,18); 7,3131 (4,06); 7,2862 (10,86); 7,2817 (9,77); 7,2675 (8,4); 7,2632 (7,33); 5,7563 (1,63); 3,5514 (4,91); 3,5349 (12,73); 3,52 (12,94); 3,5035 (5,34); 3,3246 (50,97); 2,9529 (8,35); 2,9362 (16); 2,9194 (7,34); 2,6757 (0,47); 2,6711 (0,64); 2,6667 (0,47); 2,5242 (2,43); 2,511 (36,71);

3-chlor-4- 2,5066 (72,13); 2,502 (94,54); 2,4974 (68,73); 2,493 (trifluormethyl)- (33,14); 2,3334 (0,44); 2,3288 (0,59); 2,3243 (0,42);

1,9891 (0,61); 1,3364 (0,95); 1,2588 (0,35); 1,2496

20-199 2-brom-phenyl henyl CH2 CH2 H (1,17); 1,2339 (0,37); 1,1753 (0,35)

Verbindung Nr. 20-200, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4788 (3,08); 8,465 (5,95); 8,4511 (3,02); 7,8692 (10,01); 7,867 (10,49); 7,8495 (10,79); 7,8472 (10,6); 7,7997 (11,51); 7,7795 (13); 7,7683 (0,59); 7,661 (13,75); 7,4828 (7,36); 7,4624 (6,49); 7,4404 (5,13); 7,4377 (5,23); 7,4217 (11,29); 7,419 (11,3); 7,4111 (0,72); 7,4029 (7,01); 7,4002 (6,74); 7,3372 (0,34); 7,2584 (0,37); 7,2206 (9,34); 7,2166 (11,24); 7,2017 (8,47); 7,1976 (8,89); 7,1715 (6,6); 7,1673 (5,81); 7,1524 (9,49); 7,1481 (8,44); 7,1332 (5,61); 7,129 (4,91); 5,7563 (1,07); 3,5381 (4,97); 3,5212 (12,89); 3,5065 (13,12); 3,4899 (5,32); 3,3242 (74,03); 2,9609

(8.14) ; 2,9441 (16); 2,9272 (7,24); 2,6757 (0,58); 2,6711 (0,79); 2,6665 (0,57); 2,5245 (2,67); 2,5197

3-chlor-4- (4.15) ; 2,5111 (44,64); 2,5066 (89,1); 2,5021 (117,31); (trifluormethyl)- 2,4975 (83,97); 2,4929 (39,5); 2,3335 (0,56); 2,3289

(0,76); 2,3243 (0,54); 1,3364 (1,02); 1,2588 (0,36);

20-200 2-iod-phenyl henyl CH2 CH2 H 1,2497 (1,31); 1,235 (0,35)

Verbindung Nr. 20-201, Solvent: [DMSO], Spektrometer:

3-chlor-4- 399.95MHz

(trifluormethyl)- 8,7981 (2,62); 8,7842 (4,9); 8,7703 (2,59); 8,3162 (0,5);

7,7851 (10,6); 7,7649 (11,86); 7,6227 (12,51); 7,5284

20-201 2,6-difluor-phenyl phenyl CH2 CH2 H (1,93); 7,5118 (4,12); 7,5073 (3,57); 7,4951 (2,73);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7,4906 [7,84); 7,4862 [2,75); 7,474 [3,73); 7,4695 [4,67); 7,4526 [2,94); 7,4453 (6,7); 7,425 (6); 7,1763 [1,56); 7,1731 [2,08); 7,1657 [13,08); 7,1464 (16); 7,1396 [2,87); 7,1364 (1,91); 7,1256 [10,89); 7,1179 (1,87); 5,7564 [0,86); 3,5647 (4,53); 3,5484 [11,52); 3,5333 (11,71); 3,517 (5); 3,3236 (106,45); 2,9342 [7,65); 2,9175 (14,63); 2,9008 [6,78); 2,68 (0,39); 2,6756 [0,78); 2,6711 (1,05); 2,6665 [0,76); 2,6619 (0,37); 2,5244 [3,34); 2,5196 (5,14); 2,5111 [57,3); 2,5066 (114,12); 2,502 [149,98); 2,4974 (107,21); 2,4929 [50,27); 2,3333 (0,69); 2,3287 [0,95); 2,3241 (0,67); 1,3362 [0,96); 1,2987 (0,38); 1,2588 [0,56); 1,2497 (1,16); -0,0002 (0,34)

Verbindung Nr. 20-202, Solvent: [DMSO], Spektrometer: 399.95MHz8,6764 (2,27); 8,6628 [4,25); 8,6489 (2,2); 8,4592 (9); 8,4543 (9,56); 8,4471 [9,62); 8,4422 (9,29); 8,3161 [0,32); 7,8006 (16); 7,796 [11,26); 7,7819 (14,57); 7,7773 [15,71); 7,6539 (10,46); 7,4938 [10,79); 7,4818 (10,64); 7,4749 [13,18); 7,4629 (10,11); 7,4516 [4,96); 3,5741 (3,92); 3,5575 [9,92); 3,5427 (10,16); 3,5262 [4,29); 3,324 (68,76); 2,9545 [6,38); 2,9377 (12,33); 2,921 [5,67); 2,676 (0,56); 2,6714 [0,75);

3-chlor-4- 2,6668 (0,53); 2,5248 [2,58); 2,5201 (3,92); 2,5115

(trifluormethyl)- (40,93); 2,5069 (81,65); 2,5023 [107,36); 2,4977

(76,49); 2,4932 [35,59); 2,3338 (0,5); 2,3291 [0,69);

20-202 2-chlor-3-pyridyl phenyl CH2 CH2 H 2,3245 (0,48); 1,2346 (0,4)

Verbindung Nr. 20-203, Solvent: [DMSO], Spektrometer: 399.95MHz8,3685 (1,63); 7,7254 [4,36); 7,7209 (4,58); 7,658 [2,84); 7,6374 (5,04); 7,5891 [3,01); 7,5847 (2,86); 7,5684 (1,7); 7,564 (1,64); 7,532 [0,62); 7,5274 (1,05); 7,5174 [1,91); 7,513 (3,09); 7,51 [2,64); 7,4955 (4,99); 7,477 [3,74); 7,2851 (1,85); 7,2833 (2,1); 7,2762 (0,56); 7,2683 [2,73); 7,266 (3,14); 7,2587 [2,65); 7,2491 (4,13); 7,2368 [1,71); 7,2345 (1,58); 7,2309 [2,39); 7,2285 (1,72); 5,757 (16); 4,0389 (0,72); 4,021 (0,73); 3,5404 (1,77); 3,5239 [4,69); 3,5088 (4,8); 3,4925 [1,95); 3,3274 (33,84); 2,9424 [3,57); 2,9256

4-chlor-3- (7); 2,9087 [3,17); 2,5254 (0,98); 2,512 [13,42); 2,5076

(trifluormethyl)- (26,45); 2,5031 [34,87); 2,4985 (25,69); 2,4941 [12,73);

1,9896 (3,14); 1,1934 [0,86); 1,1757 (1,69); 1,1578

20-203 2-fluor-phenyl phenyl CH2 CH2 H (0,83)

Verbindung Nr. 20-204, Solvent: [DMSO], Spektrometer:

4-chlor-3- 399.95MHz

20-204 2-chlor-phenyl (trifluormethyl)- CH2 CH2 H 8,4836 (2,64); 8,47 (4,99); 8,4563 (2,63); 7,7429

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,5999 (7,87); 7,5954 (7,37); 7,5793 (4,25); 7,5747

(4.05) ; 7,53 (1,93); 7,5134 (4,14); 7,5088 (3,63); 7,4967 (2,74); 7,4922 (7,8); 7,4878 (2,84); 7,4755 (3,74); 7,4711 (4,62); 7,4545 (2,12); 7,1729 (1,5); 7,1697

(2.06) ; 7,1622 (12,76); 7,1429 (15,99); 7,1222 (10,82); 7,1144 (1,86); 3,5576 (4,64); 3,5418 (11,5); 3,5261 (11,46); 3,5103 (5,07); 3,336 (50,94); 2,9315 (8,91); 2,9149 (16); 2,8984 (7,89); 2,6788 (0,42); 2,5322 (1,35); 2,5188 (24,17); 2,5144 (48,32); 2,5098 (63,36); 2,5052 (45,64); 2,5007 (21,7); 2,3366 (0,39); 1,9967 (0,81); 1,3443 (0,52); 1,2569 (0,68); 1,1826 (0,45)

Verbindung Nr. 20-208, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6587 (2,09); 8,6452 (3,95); 8,6312 (2,08); 8,4642 (6,75); 8,4593 (7,11); 8,4521 (7,2); 8,4473 (6,94); 7,7823 (6,93); 7,7774 (7,11); 7,7634 (16); 7,7586 (15,98); 7,6796 (5,02); 7,659 (10,65); 7,6263 (6,31); 7,6219 (5,79); 7,6056 (2,96); 7,6011 (2,87); 7,4946 (7,83); 7,4825 (7,7); 7,4757 (7,03); 7,4637 (6,84); 5,7645 (2,19); 3,5661 (3,47); 3,5498 (8,9); 3,5346 (9,03); 3,5184 (3,75); 3,3335 (49,48); 2,9519 (7,51);

4-chlor-3- 2,9355 (12,51); 2,9188 (5,82); 2,6834 (0,33); 2,6788

(0,44); 2,6743 (0,33); 2,532 (1,66); 2,5187 (26,53); (trifluormethyl)- 2,5143 (51,52); 2,5097 (66,81); 2,5052 (48,07); 2,5008

20-208 2-chlor-3-pyridyl henyl CH2 CH2 H (23,02); 2,3409 (0,32); 2,3366 (0,42)

Verbindung Nr. 20-209, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3568 (4,49); 7,4915 (0,95); 7,4869 (1,13); 7,4782 (1,06); 7,4734 (2,25); 7,4687 (1,73); 7,4661 (1,54); 7,4595 (1,54); 7,4577 (1,52); 7,4538 (2,46); 7,4477 (1,56); 7,4391 (1,28); 7,4344 (1,45); 7,4241 (1,8); 7,4197 (1,77); 7,4054 (3,52); 7,4012 (3,38); 7,3868 (1,84); 7,3828 (2); 7,3596 (0,9); 7,3533 (8,9); 7,3484 (2,99); 7,3373 (3,71); 7,3322 (14,7); 7,3261 (1,84); 7,2696 (1,72); 7,2636 (12,72); 7,2586 (3,45); 7,2472

(2.8) ; 7,2425 (8,07); 7,2348 (3,6); 7,2303 (3,9); 7,2279

(3.09) ; 7,2116 (6,94); 7,2093 (8,93); 7,1929 (2,33); 7,1901 (4,62); 3,3262 (84,15); 2,9374 (16); 2,6705 (0,33); 2,5407 (1,6); 2,5239 (0,86); 2,5191 (1,31); 2,5106 (18,22); 2,506 (37,1); 2,5014 (49,66); 2,4968 (36,13); 2,4922 (17,09); 0,8343 (2,26); 0,8267 (1,69); 0,8191 (5,43); 0,8151 (7,12); 0,8052 (4,25); 0,7937 (1,34); 0,7702 (1,45); 0,7584 (3,94); 0,7485 (6,72);

20-209 2-fluor-phenyl 4-chlor-phenyl CH2 C(CH2CH2) H 0,7373 (1,7); 0,7296 (1,91); -0,0002 (9,57)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

Verbindung Nr. 20-210, Solvent: [DMSO], Spektrometer: 399.95MHz

8,9582 [1,12); 8,9452 [2,08); 8,9318 (1,1); 7,5474 (0,75); 7,5308 (1,61); 7,5263 (1,46); 7,5139 (1,11); 7,5096 (3,06); 7,5053 (1,13); 7,4929 (1,52); 7,4885 (1,8); 7,472 (0,82); 7,1916 (0,65); 7,1884 (0,86); 7,181 (5,21); 7,1715 (4,05); 7,1672 (7,93); 7,1623 (9,59); 7,1408 (4,31); 7,1331 (0,74); 7,0575 (16); 7,0531 (14,9); 4,1665 (3,76); 4,1531 (7,87); 4,1396 (4,16); 3,6263 (2,11); 3,6128 (5,63); 3,5992 (5,41); 3,5856 (1,88); 3,3347 (320,34); 3,2913 (0,49); 2,676 (0,59); 2,6716 (0,82); 2,6671 (0,58); 2,5417 (6,89); 2,5248 (2,24); 2,5114 (47,18); 2,507 (93,86); 2,5024 (124,14); 2,4979 (91,68); 2,4935 (44,8); 2,3336 (0,6); 2,3293

20-210 2-fluor-phenyl 3,5- dichlorpheny 1 0 CH2 CH2 H (0,8); 2,3247 (0,58); -0,0002 (1,97)

Verbindung Nr. 20-211, Solvent: [DMSO], Spektrometer: 601.6MHz

8,3712 (0,32); 8,3612 (0,6); 7,7448 (0,86); 7,7319 (1,03); 7,679 (0,38); 7,6665 (0,93); 7,6541 (0,61); 7,6171 (0,6); 7,6043 (0,84); 7,5916 (0,33); 7,4266 (1,45); 7,4246 (1,74); 7,4213 (0,56); 7,4125 (2,19); 7,4107 (1,98); 7,336 (1,5); 7,3327 (0,51); 7,3237 (2,15); 7,3128 (0,62); 7,31 (1,9); 7,2952 (0,87); 7,2159 (0,45); 7,2139 (0,77); 7,212 (0,45); 7,2018 (1,22); 7,1896 (0,54); 3,4473 (2,68); 3,437 (2,66); 3,3529 (192,26);

2-(trifluormethyl)- 2,5419 (52,5); 2,5236 (0,43); 2,5206 (0,52); 2,5174

(0,56); 2,5087 (7,11); 2,5057 (14,84); 2,5027 (20,52);

20-211 phenyl phenyl C(CH3)2 CH2 H 2,4996 (14,91); 2,4966 (7); 1,3128 (16); -0,0002 (1,31)

Verbindung Nr. 20-212, Solvent: [DMSO], Spektrometer: 601.6MHz

8,5726 (0,34); 8,5631 (0,64); 8,5535 (0,33); 7,7481 (0,86); 7,7351 (1,04); 7,6999 (0,4); 7,6874 (0,93); 7,6749 (0,58); 7,6258 (0,57); 7,613 (0,84); 7,6003 (0,34); 7,3496 (1,07); 7,3384 (16); 3,4961 (2,13); 3,4863 (2,1); 3,3273 (54,56); 2,5406 (22,25); 2,5223 (0,38); 2,5192 (0,46); 2,516 (0,52); 2,5072 (6,3); 2,5043 (12,78); 2,5013 (17,29); 2,4983 (12,72); 2,4955 (6,06);

2-(trifluormethyl)- 0,984 (0,71); 0,9763 (1,97); 0,9736 (2,04); 0,9663

(0,77); 0,7936 (0,79); 0,7863 (1,93); 0,7837 (2,02);

20-212 phenyl 4-chlor-phenyl C(CH2CH2) CH2 H 0,7759 (0,63); -0,0002 (0,86)

Verbindung Nr. 20-213, Solvent: [DMSO], Spektrometer:

2-(trifluormethyl)- 601.6MHz

8,5397 (2,01); 8,5297 (3,92); 8,5197 (1,95); 7,7446

20-213 phenyl 2,4-dichlor-phenyl C(CH2CH2) CH2 H (4,99); 7,7316 (6,04); 7,7057 (2,3); 7,6932 (5,41);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7,6807 [3,37); 7,6269 [3,34); 7,6141 [4,85); 7,6014 [2,04); 7,5611 [13,34); 7,5576 [13,68); 7,427 [0,35); 7,4177 (8,4); 7,4039 (16); 7,3773 [11,18); 7,3737 (10,29); 7,3636 (6,12); 7,3599 [9,03); 7,3451 (5); 3,4554 [4,44); 3,4463 (4,37); 3,3233 [773,98); 3,3042 (0,59); 3,3003 [0,51); 2,6528 (0,85); 2,619 [0,68); 2,616 (1,35); 2,6129 [1,83); 2,6099 (1,33); 2,6068 [0,65); 2,5406 (279,05); 2,5222 [5,54); 2,5191 (7,02); 2,516 [7,69); 2,5073 (97,86); 2,5042 [206,44); 2,5012 (288,66); 2,4981 [208,21); 2,495 (95,86); 2,4241 (0,8); 2,3915 (0,57); 2,3884 [1,25); 2,3854 (1,71); 2,3823 [1,22); 2,3793 (0,53); 2,0736 [0,39); 1,0481 (3,83); 1,0401 [11,37); 1,0377 (12,07); 1,03 [3,95); 0,7727 (4,41); 0,7649 [10,69); 0,7626 (11,23); 0,7545 [3,63); 0,0052 (0,69); -0,0002 (20,39); -0,0057 (0,65)

Verbindung Nr. 20-214, Solvent: [DMSO], Spektrometer: 601.6MHz

8,398 [0,37); 8,3879 (0,73); 8,3777 [0,36); 7,7345 (0,95); 7,7217 [1,13); 7,6756 (1,04); 7,6612 (4,3); 7,6502 (3,36); 7,6359 [0,95); 7,6121 (0,65); 7,5993 [0,91); 7,5867 (0,36); 7,2984 [1,03); 7,2859 (0,96); 3,5028 [2,67); 3,4924 (2,64); 3,3267 [77,64); 2,5409

2-(trifluormethyl)- 4-(trifluormethyl)- (61,72); 2,5226 [0,35); 2,5195 (0,45); 2,5164 [0,48);

2,5077 (8,46); 2,5046 [18,04); 2,5016 (25,25); 2,4985

20-214 phenyl phenyl C(CH3)2 CH2 H (18,22); 2,4955 (8,44); 1,3494 (16); -0,0002 (1,75)

Verbindung Nr. 20-215, Solvent: [DMSO], Spektrometer: 601.6MHz

8,3664 [0,35); 8,3563 (0,69); 8,346 [0,35); 7,7328 (0,9); 7,7199 [1,09); 7,6759 (0,4); 7,6642 [0,98); 7,6517 (0,64); 7,6113 [0,62); 7,5985 (0,88); 7,5859 [0,35); 7,4331 (2,43); 7,419 [3,37); 7,4113 (1,89); 7,4071 (2,1); 7,3454 (1,76); 7,3411 [1,53); 7,3313 (1,25); 7,3271 [1,18); 7,3117 (0,99); 7,2991 [0,92); 3,7889 (2,65); 3,7785 [2,62); 3,325 (131,07); 2,5406 [81,64); 2,5327

2-(trifluormethyl)- (0,35); 2,5223 [0,64); 2,5192 (0,8); 2,516 [0,84); 2,5073

(14,15); 2,5043 [30,1); 2,5012 (42,22); 2,4981 [30,52);

20-215 phenyl 2,5-dichlor-phenyl C(CH3)2 CH2 H 2,4951 (14,18); 1,465 (16); -0,0002 (3,13)

Verbindung Nr. 20-216, Solvent: [DMSO], Spektrometer: 601.6MHz

8,3734 [0,36); 8,3632 (0,7); 8,353 [0,35); 7,7416 (0,94); 7,7286 [1,13); 7,6847 (0,41); 7,6727 [1,01); 7,6602

2-(trifluormethyl)- (0,64); 7,6172 [0,63); 7,6044 (0,92); 7,5917 [0,36);

7,4398 (2,65); 7,4363 [0,89); 7,4288 (1,07); 7,4253

20-216 phenyl 4-chlor-phenyl C(CH3)2 CH2 H (4,02); 7,4206 (0,45); 7,3691 (0,48); 7,3645 (4,06);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

7,361 [1,04); 7,3535 [0,88); 7,35 [2,75); 7,3228 [1,02); 7,3103 [0,94); 3,4388 (2,7); 3,4284 [2,67); 3,3265 (68,14); 2,5406 (55,44); 2,5192 (0,4); 2,5161 (0,42); 2,5073 [7,55); 2,5043 (15,85); 2,5012 [21,96); 2,4982 (15,84); 2,4951 (7,33); 1,3026 (16); -0,0002 (1,45)

Verbindung Nr. 20-217, Solvent: [DMSO], Spektrometer: 601.6MHz

8,5501 (1,51); 8,5407 [2,84); 8,5312 (1,48); 7,7456 [4,13); 7,7326 (4,97); 7,6896 [1,84); 7,6772 (4,47); 7,6648 [2,86); 7,6206 (2,77); 7,6078 [4,01); 7,5952 (1,6); 7,3335 [7,25); 7,3312 (10,76); 7,3197 (16); 7,3179 (14,72); 7,3031 [9,87); 7,2995 (2,28); 7,2908 [10,7); 7,2803 (2,29); 7,2775 [5,07); 7,2016 (2,13); 7,1993 [3,94); 7,1968 (2,12); 7,1903 [2,23); 7,1874 (5,39); 7,1843 (1,8); 7,1778 (1,37); 7,1754 [2,43); 7,1731 (1,23); 3,52 [11,5); 3,5103 (11,38); 3,3536 (0,4); 3,3264 (380,29); 2,6526 [0,91); 2,6157 (0,52); 2,6126 [0,73); 2,6096 (0,53); 2,5609 [0,35); 2,5402 (291,54); 2,5219 (1,7); 2,5188 (2,12); 2,5157 [2,37); 2,507 (40,83); 2,5039 [86,4); 2,5008 (119,69); 2,4978 [86,54); 2,4948 (39,49); 2,4242 [0,88); 2,3881 (0,51); 2,385

2-(trifluormethyl)- [0,7); 2,382 (0,49); 2,073 [0,43); 0,9721 (3,92); 0,9645

(10,49); 0,9616 (10,73); 0,9545 [4,36); 0,79 (4,26);

20-217 henyl phenyl C(CH2CH2) CH2 H 0,7829 (10); 0,78 (10,5); 0,7724 (3,39); -0,0002 (8,02)

Verbindung Nr. 20-218, Solvent: [DMSO], Spektrometer: 601.6MHz

8,3691 (0,37); 8,3589 [0,73); 8,3486 (0,37); 7,7374 [0,99); 7,7245 (1,18); 7,6841 [0,45); 7,6721 (1,06); 7,6597 (0,7); 7,6154 (0,68); 7,602 (3,23); 7,5982 (2,56); 7,5901 [0,43); 7,5591 (2,32); 7,545 [2,82); 7,4116 (1,38); 7,4078 [1,33); 7,3975 (1,16); 7,3937 [1,14); 7,3232 (1,05); 7,3106 [0,98); 3,4588 (2,73); 3,4484 (2,65); 3,3432 (0,49); 3,3238 [270,15); 3,3093 (0,43); 3,3063 [0,36); 2,6528 (0,38); 2,616 [0,47); 2,613 (0,64); 2,6099 [0,46); 2,5406 (117,72); 2,526 [0,33); 2,5223 (1,41); 2,5191 (1,8); 2,516 (2,19); 2,5073 [35,67); 2,5042 (75,52); 2,5012 [105,59); 2,4981 (77,29); 2,4951

2-(trifluormethyl)- [35,91); 2,4243 (0,37); 2,3884 [0,46); 2,3854 (0,63);

2,3823 [0,45); 2,0124 (0,73); 1,3116 (16); -0,0002 henyl 3 ,4-dichlor-phenyl C(CH3)2 CH2 H (6,06)

Verbindung Nr. 20-219, Solvent: [DMSO], Spektrometer:

2-(trifluormethyl)- 601.6MHz

8,36 [0,35); 8,3499 (0,66); 8,3396 [0,34); 7,735 (0,9);

20-219 phenyl 2-chlorphenyl C(CH3)2 CH2 H 7,7222 (1,07); 7,6692 (0,4); 7,657 (0,96); 7,6445 (0,64);

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7,7409 (3,28); 7,7345 (7,1); 7,7279 (6); 7,7238 (7,51); 7,705 (5,09); 7,6609 (4,87); 7,6418 (6,27); 7,6228 (2,37); 7,5787 (8,93); 7,5583 (7,28); 7,4849 (7,39); 7,4661 (6,34); 7,3367 (0,42); 7,3321 (0,37); 7,1813 (0,58); 7,1758 (0,39); 3,5065 (3,67); 3,4895 (7,83); 3,4734 (7,66); 3,4557 (4,14); 3,3226 (200,35); 2,9985 (5,53); 2,9806 (9,48); 2,9626 (4,7); 2,6799 (0,64); 2,6754 (1,37); 2,6709 (1,86); 2,6663 (1,32); 2,6617 (0,6); 2,5243 (5,39); 2,5195 (8,41); 2,5109 (101,48); 2,5064 (204,34); 2,5018 (270,53); 2,4972 (194,79); 2,4926 (91,36); 2,3377 (0,65); 2,3331 (1,33); 2,3286 (1,82); 2,324 (1,3); 2,3195 (0,59); 1,3515 (0,41); 1,3358 (6,85); 1,2983 (0,59); 1,2586 (1,06); 1,2495 (8,87); 1,2348 (1,2); 1,1873 (0,53); 0,008 (2,54); -0,0002 (78,69); -0,0085 (2,37)

Verbindung Nr. 20-224, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5833 (0,65); 8,5693 (1,25); 8,5555 (0,67); 7,7815 (1,35); 7,7631 (1,8); 7,7603 (1,63); 7,6881 (0,5); 7,6712 (1,49); 7,6537 (1,97); 7,6498 (2,18); 7,6302 (1,38); 7,6115 (0,45); 7,3078 (1,6); 7,2903 (1,45); 7,2094 (0,44); 7,2006 (4,34); 7,1954 (1,41); 7,183 (1,61); 7,1779 (4,71); 7,169 (0,5); 6,7781 (0,53); 6,7694 (4,55); 6,7642 (1,52); 6,7467 (4,06); 6,738 (0,44); 3,4883 (1,08); 3,4717 (2,81); 3,4556 (2,25); 3,3963 (1,23); 3,3815 (2,43); 3,3657 (1,97); 3,3495 (0,75); 3,3265

2-(trifluormethyl)- (39,84); 2,9281 (16); 2,5409 (17,33); 2,5058 (24,19);

20-224 phenyl 4-chlor-phenyl N(CH3) CH2 CH2 H 2,5014 (30,73); 2,497 (22,57); -0,0002 (4,72)

Verbindung Nr. 20-225, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7362 (1,45); 8,7229 (2,72); 8,7094 (1,45); 7,7839 (3,37); 7,7645 (4,5); 7,7373 (1,5); 7,7189 (3,82); 7,7004 (2,86); 7,6614 (2,7); 7,6425 (3,42); 7,6235 (1,26); 7,5073 (4,07); 7,4886 (3,43); 7,1703 (3,45); 7,1663 (6,46); 7,1622 (3,93); 7,0563 (16); 7,0519 (14,71); 4,1638 (4,37); 4,1501 (9,22); 4,1365 (4,76); 3,6059 (2,44); 3,5922 (6,57); 3,5784 (6,33); 3,5647 (2,19);

2-(trifluormethyl)- 3,3284 (64,9); 2,9286 (0,36); 2,5415 (31,56); 2,5066

20-225 phenyl 3,5-dichlorphenyl 0 CH2 CH2 H (38,19); 2,5022 (49,01); 2,4979 (36,35); -0,0003 (6,28)

Verbindung Nr. 20-226, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5298 (2,87); 8,5092 (2,91); 7,7838 (3,39); 7,7644

2-(trifluormethyl)- 3 -(trifluormethyl)- (4,53); 7,7343 (1,49); 7,7159 (3,75); 7,6973 (2,79);

20-226 phenyl phenyl 0 CH2 CH(CH2CH3) H 7,6765 (0,4); 7,6571 (2,91); 7,6379 (3,45); 7,6189

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ L- Patent-Nr.

(1,29); 7,5597 (1,81); 7,5401 (4,09); 7,5203 (2,56); 7,4809 (3,98); 7,4623 (3,43); 7,3549 (0,53); 7,3351 (0,96); 7,3087 (3,63); 7,2888 (5,95); 7,2576 (5,29); 4,2022 (0,69); 4,1888 (1,09); 4,1811 (1,4); 4,168 (1,63); 4,1569 (1,08); 4,1463 (0,84); 4,1336 (0,43); 4,0839 (9,92); 4,0701 (5,47); 3,3269 (88,33); 2,6755 (0,44); 2,6711 (0,57); 2,5413 (23,4); 2,5065 (69,88); 2,5022 (86,63); 2,4979 (62,85); 2,3291 (0,56); 1,7584 (0,45); 1,7518 (0,82); 1,7395 (1,11); 1,7332 (1,06); 1,7197 (1,56); 1,7052 (1,39); 1,6991 (1,37); 1,6869 (1,23); 1,67 (0,49); 1,5914 (1,16); 1,5725 (1,64); 1,5563 (1,32); 1,5512 (1,47); 1,5379 (1,17); 1,5349 (1,16); 1,5167 (0,82); 0,9882 (7,77); 0,9697 (16); 0,9512 (6,94); 0,0077 (0,75); -0,0003 (13,51); -0,0085 (0,57)

Verbindung Nr. 20-227, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4853 (2,14); 8,4642 (2,18); 7,7612 (2,61); 7,7416 (3,53); 7,7244 (1,2); 7,7067 (3); 7,688 (2,06); 7,6415 (2,07); 7,6223 (2,75); 7,6 (4,88); 7,5965 (5,78); 7,5942 (4,18); 7,4248 (0,48); 7,4039 (10,2); 7,4002 (16); 7,3813 (0,44); 7,3189 (3,06); 7,3001 (2,79); 4,3174 (0,49); 4,2979 (1,12); 4,281 (1,55); 4,2641 (1,05); 4,2605 (1,04); 4,244 (0,54); 3,3971 (0,45); 3,3372 (602,52); 3,2859 (0,46); 2,8992 (0,5); 2,8798 (5,86); 2,8648 (3,94); 2,8588 (3,89); 2,8242 (0,4); 2,6805 (0,35); 2,6759 (0,71); 2,6713 (0,96); 2,6668 (0,7); 2,6622 (0,32); 2,5416 (10,43); 2,5247 (3,11); 2,5199 (4,94); 2,5114 (56,02); 2,5069 (112,43); 2,5023 (148,76); 2,4976 (107,69); 2,4931 (51,38); 2,3382 (0,36); 2,3336 (0,7); 2,329 (0,99); 2,3244 (0,71); 2,3198

2-(trifluormethyl)- (0,33); 1,2348 (0,6); 1,1724 (12,85); 1,1558 (12,71); -

20-227 phenyl 2,4-dichlor-phenyl CH(CH3) CH2 H 0,0002 (4,01)

Verbindung Nr. 20-228, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5891 (2,45); 8,5752 (4,67); 8,5614 (2,39); 7,7985 (9,5); 7,7888 (0,77); 7,7782 (10,87); 7,7678 (6,38); 7,7484 (7,98); 7,7206 (2,63); 7,7032 (6,75); 7,6846 (4,92); 7,6465 (5,02); 7,6299 (16); 7,609 (2,33); 7,4544 (6,04); 7,4339 (5,36); 7,4104 (7,08); 7,3916 (6,21); 3,5542 (4,1); 3,5374 (10,69); 3,5227 (11,02); 3,506

3-chlor-4- (4,48); 3,3252 (57,49); 2,9335 (7,06); 2,9165 (13,45);

2,8996 (5,99); 2,6761 (0,47); 2,6715 (0,66); 2,6671

2-(trifluormethyl)- (trifluonnethyl)- (0,48); 2,5248 (2,16); 2,52 (3,39); 2,5115 (36,96); 2,507

20-228 henyl henyl CH2 CH2 H (73,51); 2,5024 (96,47); 2,4978 (68,87); 2,4933 (32,15);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

Verbindung Nr. 20-232, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8531 [3,08); 8,8392 [5,92); 8,8252 [3,06); 8,8018 [7,54); 8,7922 [7,33); 8,7902 (7,33); 7,9764 [6,39); 7,9742 [6,69); 7,957 (7,98); 7,9548 (7,94); 7,8018 (7,11); 7,79 (7,1); 7,7822 (6,23); 7,7704 (14,82); 7,7655 (16); 7,7598 (8,64); 7,7387 (7,55); 7,7336 (5,8); 7,5891 (10,13); 7,5686 (8,13); 5,759 (0,48); 3,5306 (4,19); 3,5137 [9,15); 3,497 (8,93); 3,4797 (4,64); 3,3277 (69,59); 3,0051 [6,41); 2,987 (11,03); 2,9688 (5,52); 2,6768 [0,46); 2,6724 (0,61); 2,6678 [0,47); 2,5425

4-chlor-2- (0,41); 2,5255 [2,03); 2,5122 (35,54); 2,5078 (69,77);

2,5033 [90,89); 2,4987 (66,12); 2,4943 [31,84); 2,3345

2- (trifluormethyl)- (trifluormethyl)- (0,41); 2,33 [0,56); 2,3253 (0,43); 1,337 [0,57); 1,2498

20-232 3- pyridyl phenyl CH2 CH2 H (0,71); -0,0002 (1,27)

Verbindung Nr. 20-233, Solvent: [DMSO], Spektrometer: 399.95MHz-.8,7846 (2,79); 8,7752 [2,72); 8,773 (2,72); 8,7089 [1,13); 8,6954 (2,15); 8,6817 [1,12); 8,1021 (0,88); 8,0861 [0,88); 7,8913 (2,26); 7,8888 [2,35); 7,8718 (3,2); 7,8693 (3,13); 7,7774 (2,92); 7,7657 (2,9); 7,7579 (2,22); 7,7458 (2,58); 7,7393 (4,5); 7,7349 (4,57); 7,6744 (2,78); 7,6539 (5,25); 7,6117 (3,14); 7,6073 [2,9); 7,591 (1,66); 7,5866 (1,56); 6,5865 (1,27); 6,5826 [0,93); 6,5741 (0,92); 6,5702 [1,22); 3,5655 (1,77); 3,5492 [4,57); 3,5341 (4,64); 3,5178 (1,91);

4-chlor-3- 3,3285 [14,34); 2,9429 (16); 2,9273 [3,41); 2,9106

(6,49); 2,8938 [3,01); 2,5252 (0,74); 2,5119 [12,14);

2- (trifluormethyl)- (trifluormethyl)- 2,5076 (23,36); 2,503 (30,16); 2,4985 (21,74); 2,4941

20-233 3- pyridyl phenyl CH2 CH2 H (10,4); -0,0002 (0,4)

Verbindung Nr. 20-234, Solvent: [DMSO], Spektrometer: 399.95MHz

9,1568 [1,26); 9,1415 (2,53); 9,1262 (1,29); 8,8004 (2,96); 8,7906 (3,04); 7,878 (2,33); 7,8604 (3,54); 7,8586 (3,51); 7,7917 (2,96); 7,7799 (2,93); 7,7721 (2,12); 7,7603 (1,97); 7,6316 (1,83); 7,6248 (1); 7,6088 (16); 7,6025 (15,63); 7,5862 (1,13); 7,5797 (1,96); 5,7586 [0,72); 4,0976 (1,51); 4,0819 [1,53); 4,0613 (3,39); 4,0457 [3,31); 4,0249 (1,73); 4,0092 (1,64);

2- (trifluormethyl)- 3,3248 [11,06); 2,9419 (0,37); 2,5066 [34,87); 2,5022

20-234 3- pyridyl 4-chlor-phenyl CF2 CH2 H (44,93); 2,4978 (33,89); 0,9823 (0,33); -0,0002 (0,52)

Verbindung Nr. 20-235, Solvent: [DMSO], Spektrometer: 399.95MHz

2- (trifluormethyl)- 9,1615 (2,9); 9,1459 [5,94); 9,1304 (2,87); 8,7983

20-235 3- pyridyl 2,4-dichlor-phenyl CF2 CH2 H [6,21); 8,7958 (6,6); 8,7866 [6,48); 8,7841 (6,4); 7,8585

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

'H-NMR (d6-DMSO): δ [ppm], 8,95 (t, 1H, NH), 8,80 - 8,79 (d, 1H), 7,99 - 7,97 (d, 1H), 7,84 (s, 1H), 7,80 - 7,77

4-chlor-2- (dd, 1H), 7,72 - 7,69 (d, 1H), 7,40 - 7,38 (d, 1H), 4,30 (t,

2- (trifluormethyl)- (trifluormethyl)- 2H), 3,70 - 3,67 (quart, 2H).

20-238 3- pyridyl phenyl 0 CH2 C(CH3)2 H

Verbindung Nr. 20-239, Solvent: [DMSO], Spektrometer: 399.9SMHz^8,951 (0,32); 8,9377 (0,62); 8,8036 (0,77); 8,794 (0,76); 8,792 (0,76); 7,9955 (0,67); 7,9934 (0,7); 7,9761 (0,83); 7,9739 (0,82); 7,8492 (1,11); 7,8441 (1,18); 7,804 (0,73); 7,7921 (0,73); 7,7845 (0,63); 7,7726 (0,6); 7,7181 (0,55); 7,7137 (0,53); 7,6963 (0,64); 7,692 (0,59); 7,4025 (1,02); 7,3808 (0,9); 5,7574 (16); 4,3186 (0,92); 4,305 (1,94); 4,2914 (0,99); 4,0391 (0,42); 4,0213 (0,43); 3,7078 (0,52); 3,6942 (1,4);

2-chlor-4- 3,6805 (1,35); 3,6669 (0,46); 3,3318 (21,81); 2,5123

(4,13); 2,508 (8,08); 2,5035 (10,5); 2,499 (7,65); 2,4947

2- (trifluormethyl)- (trifluormethyl)- (3,74); 1,99 (1,83); 1,1935 (0,5); 1,1757 (1); 1,1579

20-239 3- pyridyl phenyl 0 CH2 CH2 H (0,49); -0,0002 (3,87)

Verbindung Nr. 20-240, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7725 (0,93); 8,7632 (0,91); 8,7611 (0,92); 8,5433 (1,63); 7,8661 (0,81); 7,8558 (1,46); 7,8503 (2,44); 7,7737 (0,97); 7,7619 (0,94); 7,7542 (0,69); 7,7423 (0,66); 7,71 (0,67); 7,7057 (0,66); 7,6883 (0,76); 7,6839

2-chlor-4- (0,73); 7,3506 (1,22); 7,3289 (1,11); 4,3551 (4,79);

3,3246 (8,95); 2,5247 (0,34); 2,5114 (6,89); 2,507

2- (trifluormethyl)- (trifluormethyl)- (13,73); 2,5024 (18,07); 2,4979 (13,26); 2,4935 (6,54);

20-240 3- pyridyl phenyl 0 CH2 C(CH3)2 H 1,9896 (0,35); 1,4658 (16); -0,0002 (7,67)

2-chlor-4- (trifluormethyl)-3 -

20-241 pyridyl 4-chlor-phenyl CH2 C(CH3)2 H

Verbindung Nr. 20-242, Solvent: [DMSO], Spektrometer: 399.95MHz

9,0439 (3,42); 9,0299 (6,6); 9,0159 (3,34); 8,7506 (11,17); 8,7495 (10,82); 8,7376 (11,57); 7,8965 (16); 7,8835 (15,34); 7,8399 (0,45); 7,8355 (0,41); 7,7725 (11,36); 7,7671 (15,91); 7,7537 (7,12); 7,7483 (4,17); 7,733 (8,46); 7,7276 (6,72); 7,6197 (11,83); 7,5989

2-chlor-4- 4-chlor-2- (8,77); 7,3152 (0,34); 5,7588 (3,52); 3,8307 (1,77);

3,5599 (4,64); 3,5435 (8,9); 3,523 (8,82); 3,5078 (5,19); (trifluormethyl)-3 - (trifluormethyl)- 3,3256 (75,52); 3,0172 (7,11); 2,9983 (11,12); 2,9798

20-242 pyridyl phenyl CH2 CH2 H (6,09); 2,6812 (0,33); 2,6768 (0,62); 2,6723 (0,84);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

2,6678 (0,6); 2,5256 (2,62); 2,5122 (46,03); 2,5078 (90,6); 2,5032 (117,63); 2,4987 (84,07); 2,4942 (39,46); 2,3347 (0,54); 2,33 (0,74); 2,3253 (0,52); 2,1844 (0,74); 1,3367 (2,34); 1,2993 (0,89); 1,2589 (1,31); 1,2497 (2,77); 1,2339 (0,41); 1,1382 (5,8); 0,008 (1,9); -0,0002 (53,16); -0,0085 (1,59)

Verbindung Nr. 20-243, Solvent; [DMSO], Spektrometer; 399.95MHz

8,8583 (3); 8,8447 (5,73); 8,8309 (2,98); 8,7221 (10); 8,7208 (9,89); 8,7092 (10,38); 7,8632 (14,23); 7,8502 (13,59); 7,748 (11,74); 7,7439 (11,97); 7,6725 (5,96); 7,6518 (16); 7,6307 (9,56); 7,6262 (8,74); 7,6099 (3,56); 7,6054 (3,5); 5,7588 (0,85); 3,6159 (4,32); 3,5997 (11,07); 3,5845 (11,29); 3,5683 (4,65); 3,3266 (40,13); 2,9408 (8,41); 2,9241 (15,96); 2,9074 (7,58); 2,6766 (0,39); 2,6721 (0,52); 2,6675 (0,38); 2,5255 (1,76); 2,5206 (2,85); 2,5121 (29,87); 2,5077 (58,63);

2-chlor-4- 4-chlor-3- 2,5031 (76,27); 2,4986 (55,17); 2,4941 (26,47); 2,3344

(0,36); 2,3298 (0,5); 2,3254 (0,36); 2,1873 (0,58);

(trifluorniethyl)-3- (trifluormethyl)- 1,3371 (1,8); 1,2995 (0,61); 1,2589 (0,9); 1,2498 (2,23);

20-243 pyridyl phenyl CH2 CH2 H 0,008 (1,46); -0,0002 (37,48); -0,0085 (1,27)

Verbindung Nr. 20-244, Solvent: [DMSO], Spektrometer: 399.95MHz-.9,2553 (1,9); 9,24 (3,77); 9,2246 (1,84); 8,737 (5,97); 8,7359 (5,97); 8,724 (6,15); 7,8753 (8,49); 7,8623 (8,16); 7,6489 (6,1); 7,627 (16); 7,6018 (15,49); 7,58 (5,73); 5,758 (0,43); 4,1597 (2,23); 4,1442 (2,25); 4,1229 (4,63); 4,1073 (4,43); 4,0859 (2,57); 4,0703 (2,41); 4,0558 (0,64); 4,038 (1,71); 4,0202 (1,73); 4,0024 (0,58); 3,3245 (78,05); 2,6755 (0,53); 2,671 (0,69); 2,6665 (0,5); 2,5242 (2,31); 2,5109 (38,2); 2,5064 (75,12); 2,5019 (97,93); 2,4973 (70,45); 2,4929 (33,55); 2,3331 (0,46); 2,3286 (0,62); 2,3242 (0,45);

2-chlor-4- 2,1846 (0,94); 1,9891 (7,45); 1,3361 (3,24); 1,2583

(0,49); 1,2493 (3,95); 1,2369 (0,63); 1,1925 (2,08); (trifluormethyl)-3 - 1,1876 (0,4); 1,1747 (4,01); 1,1569 (1,97); 0,9926

20-244 pyridyl 4-chlor-phenyl CF2 CH2 H (0,45); 0,0079 (0,51); -0,0002 (13,56); -0,0085 (0,43)

Verbindung Nr. 20-245, Solvent: [DMSO], Spektrometer: 399.95MHz

9,296 (1,59); 9,2805 (3,23); 9,2648 (1,54); 8,738 (4,86); 8,7253 (4,97); 7,877 (6,65); 7,8639 (6,36); 7,8307

2-chlor-4- (5,02); 7,8262 (5,22); 7,6706 (4,09); 7,6492 (7,88);

7,634 (0,38); 7,6094 (4,6); 7,6045 (4,31); 7,5882 (2,31); (trifluormethyl)-3 - 7,5832 (2,42); 5,7581 (16); 4,2989 (1,42); 4,2834

20-245 pyridyl 2,4-dichlor-phenyl CF2 CH2 H (1,49); 4,2623 (3,08); 4,2468 (2,95); 4,2254 (1,67);

Physikalische Daten: 'H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

2-chlor-4- 2-chlor-4-

(trifluormethyl)-3 - (trifluormethyl)-

20-250 pyridyl phenyl 0 CH2 C(CH3)2 H

2-chlor-4-

(trifluormethyl)-5-

20-251 pyridyl 4-chlor-phenyl CH2 C(CH3)2 H

2-chlor-4- 4-chlor-2-

(trifluormethyl)-5- (trifluormethyl)-

20-252 pyridyl phenyl CH2 CH2 H

2-chlor-4- 4-chlor-3-

(trifluormethyl)-5- (trifluormethyl)-

20-253 pyridyl phenyl CH2 CH2 H

2-chlor-4-

(trifluormethyl)-5-

20-254 pyridyl 4-chlor-phenyl CF2 CH2 H

2-chlor-4-

(trifluormethyl)-5-

20-255 pyridyl 2,4-dichlor-phenyl CF2 CH2 H

2-chlor-4-

(trifluormethyl)-5- 2,4,6-trichlor-

20-256 pyridyl phenyl 0 CH2 CH2 H

2-chlor-4- 4-chlor-2-

(trifluormethyl)-5- (trifluormethyl)-

20-257 pyridyl phenyl 0 CH2 CH2 H

2-chlor-4- 4-chlor-2-

(trifluormethyl)-5- (trifluormethyl)-

20-258 pyridyl phenyl 0 CH2 C(CH3)2 H

2-chlor-4- 2-chlor-4-

(trifluormethyl)-5- (trifluormethyl)-

20-259 pyridyl phenyl 0 CH2 CH2 H

2-chlor-4- 2-chlor-4-

20-260 (trifluormethyl)-5- (trifluormethyl)- 0 CH2 C(CH3)2 H

Physikalische Daten: Ή-NMR, ö [ppm] oder CAS- bzw.

Bsp.-Nr. X L ¹ Patent-Nr.

pyridyl phenyl

Verbindung Nr. 20-261, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0866 (0,97); 7,8342 (1,25); 7,829 (1,33); 7,6904 (0,62); 7,6861 [0,59); 7,6687 [0,71); 7,6644 (0,66); 7,5067 (0,35); 7,5005 (0,54); 7,4958 (0,66); 7,4934 (0,64); 7,4889 [0,7); 7,4817 (0,97); 7,4771 (1,43); 7,4712 (0,68); 7,4625 (0,48); 7,4584 (0,81); 7,363 [1,14); 7,3413 [1,01); 7,262 (0,71); 7,2501 [0,87); 7,2477 (0,87); 7,2424 (0,57); 7,2379 (0,86); 7,2302

2-chlor-4- [1,4); 7,2163 [0,46); 7,2127 [1,08); 4,3728 (4,74);

3,3302 (39,12); 2,542 (5,13) 2,5251 (0,38); 2,5203 (trifluormethyl)- (0,59); 2,5116 [7,72); 2,5071 (15,68); 2,5026 (20,72)

20-261 2-fluor-phenyl henyl o CH2 C(CH3)2 H 2,498 (15,04); 2,4935 (7,22); 1,4746 (16)

Verbindung Nr. 20-262, Solvent: [DMSO], Spektrometer: 399.95MHz

7,9991 (1); 7,7034 (0,6); 7,697 (0,8); 7,6814 (0,59); 7,6749 (1,07); 7,6637 (1,85); 7,6574 (1,11); 7,5086 (0,83); 7,5037 (0,5); 7,4957 (0,6); 7,4899 (1,39); 7,4855 (1,03); 7,4783 (0,71); 7,474 (0,78); 7,4703 (0,75); 7,4672 (0,66); 7,4604 (0,44); 7,3145 (1,26); 7,2924

4-chlor-2- (1,13); 7,2663 (0,71); 7,2564 (0,84); 7,2544 (0,86);

7,2379 (1,55); 7,2184 [1,28); 4,3236 (4,82); 3,3295 (trifluormethyl)- (45,22); 2,5417 [4,44); 2,5108 (10,41); 2,5067 (19,44);

20-262 2-fluor-phenyl phenyl O CH3 C(CH3)3 H 2,5023 (24,74); 2,4978 (17,96); 1,4352 (16)

Verbindung Nr. 20-263, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4918 (2,89); 8,4875 [2,87); 7,8404 (7,83); 7,8352 [8,24); 7,7037 (3,86); 7,6994 [3,67); 7,6819 (4,55); 7,6776 (4,2); 7,6517 (3,03); 7,6472 [3,31); 7,6332 (6); 7,6285 [6,56); 7,6215 (0,73); 7,6137 [3,82); 7,6094 (3,65); 7,5628 [1,62); 7,5582 (1,61); 7,5496 (1,85) 7,5447 (3,65); 7,5418 [2,69); 7,54 (2,6); 7,5375 (2,32) 7,5307 (3,18); 7,5291 [3,02); 7,5268 (3); 7,5238 (4) 7,519 (2,14); 7,5104 [2,22); 7,5058 (1,91); 7,4167 (7,38); 7,395 [6,46); 7,3135 (4,53); 7,3007 (5,21); 7,2982 (5,76); 7,2946 [3,97); 7,2925 (4,35); 7,2887 (4,73); 7,286 (5,35); 7,2816 [9,18); 7,2798 (7,7); 7,2678 (3,46); 7,2632 (5,87); 7,2606 (3,41); 4,3333 (7,15);

2-chlor-4- 4,3188 (16); 4,3043 (7,62); 3,7101 (3,72); 3,6959

(10,66); 3,6818 (10,46); 3,6675 (3,58); 3,3317 (263,4); (trifluormethyl)- 2,6764 (0,65); 2,672 (0,87); 2,6673 (0,62); 2,5422

20-263 2-fluor-phenyl phenyl O CH2 CH2 H (29,72); 2,5252 (2,46); 2,5203 (4,06); 2,5119 (50,71);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

2,5074 [100,78); 2,5028 [131,49); 2,4982 [93,67); 2,4937 [44,06); 2,3342 [0,61); 2,3296 [0,85); 2,325 [0,61); 1,2348 [0,37); -0,0002 [0,78)

Verbindung Nr. 20-264, Solvent: [DMSO], Spektrometer: 399.95MHz

8,592 [1,48); 7,8351 [1,31); 7,8303 [1,41); 7,6905 [0,64); 7,6863 [0,63); 7,6688 [0,74); 7,6646 (0,7); 7,4834 [0,46); 7,479 [0,43); 7,4622 [0,86); 7,4455 [0,44); 7,4412 [0,52); 7,352 [1,17); 7,3304 [1,05);

2-chlor-4- 7,1327 [1,42); 7,1139 [1,84); 7,0932 (1,2); 4,3453

(trifluormethyl)- (4,68); 3,3299 (84,45); 2,5413 [8,58); 2,5242 (0,73);

2,5107 [15,63); 2,5064 (30,85); 2,502 [40,14); 2,4974

20-264 2,6-difluor-phenyl phenyl 0 CH2 C(CH3)2 H (29,57); 2,4931 (14,7); 1,4618 (16)

Verbindung Nr. 20-265, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5375 [1,39); 7,7004 (0,52); 7,6938 [0,76); 7,6783 (0,44); 7,6715 [1,19); 7,6658 (1,88); 7,6596 [0,95); 7,48 (0,44); 7,4756 [0,41); 7,4589 (0,84); 7,4422 [0,42); 7,4379 (0,51); 7,3024 [1,14); 7,2804 (1,02); 7,1292 [1,39); 7,1104 (1,72); 7,0897 [1,17); 4,2966 (4,57);

4-chlor-2- 3,3303 [132,8); 2,671 (0,37); 2,5412 [10,41); 2,5242

(trifluormethyl)- (1,19); 2,5109 [22,6); 2,5064 (44,89); 2,5019 [58,71);

2,4973 (42,49); 2,4929 [20,42); 2,3287 (0,38); 1,4199

20-265 2,6-difluor-phenyl phenyl 0 CH3 C(CH3)3 H Π6)

Verbindung Nr. 20-266, Solvent: [DMSO], Spektrometer: 399.95MHz

8,9843 [2,32); 8,9716 (4,42); 8,9582 [2,43); 7,8401 (8,68); 7,8353 (9,2); 7,7014 (4,31); 7,697 [4,13); 7,6796 (4,99); 7,6752 (4,7); 7,5476 (1,6); 7,531 [3,49); 7,5264 (3,11); 7,5142 [2,71); 7,5098 (6,7); 7,5054 [2,39); 7,4931 (3,2); 7,4887 [3,89); 7,4721 (1,79); 7,4014 [8,11); 7,3797 (7,11); 7,19 [1,32); 7,1868 (1,81); 7,1795 (10,93); 7,16 (14,22); 7,1393 [9,11); 7,1317 (1,51); 4,3087 [7,58); 4,295 (16); 4,2813 [8,06); 3,7034 (4,16); 3,6898 [11,54); 3,676 (11,27); 3,6622 [3,99); 3,3857 (0,39); 3,3668 [0,96); 3,3333 (431,43); 2,6805 [0,37); 2,676 (0,78); 2,6715 [1,07); 2,6669 (0,75); 2,6626 (0,36); 2,5418 (48,39); 2,5248 [3,19); 2,5199 (5,02);

2-chlor-4- 2,5114 [62,06); 2,507 (124); 2,5024 [162,49); 2,4978

(trifluormethyl)- (117,01); 2,4933 [55,64); 2,3381 (0,37); 2,3337 [0,77);

2,3291 (1,04); 2,3246 [0,75); 1,2352 (0,42); -0,0002

20-266 2,6-difluor-phenyl phenyl 0 CH2 CH2 H [0,34)

Verbindung Nr. 20-267, Solvent: [DMSO], Spektrometer:

20-267 2-chlor-phenyl 2-chlor-4- 0 CH2 C(CH3)2 H 399.95MHz

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(trifluomiethyl)- 8,2838 (1,48); 7,8439 (1,28); 7,8386 (1,33); 7,701

(0,62); 7,6964 (0,59); 7,679 (0,71); 7,6747 (0,66); phenyl 7,4612 (0,58); 7,4579 (0,71); 7,4412 (1,29); 7,4383

(1,43); 7,4205 (0,6); 7,4157 (0,66); 7,4029 (0,99); 7,3981 (1); 7,3834 (0,54); 7,3782 (0,61); 7,3671 (0,6); 7,3633 (0,6); 7,3556 (1,2); 7,3485 (1,22); 7,345 (1,19); 7,3312 (1,27); 7,3275 (0,78); 7,3181 (1,4); 7,3134 (1,25); 7,2995 (0,63); 7,2947 (0,47); 4,3796 (4,61); 3,3324 (119,91); 3,3118 (0,57); 2,5414 (8,32); 2,5244 (0,73); 2,5111 (16,7); 2,5066 (32,73); 2,5021 (42,5); 2,4975 (30,6); 2,4931 (14,6); 1,4677 (16)

Verbindung Nr. 20-268, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2413 (1,48); 7,7116 (0,55); 7,705 (0,77); 7,6896 (0,49); 7,683 (1,06); 7,6738 (1,84); 7,6673 (1,04); 7,4668 (0,63); 7,4632 (0,8); 7,4468 (1,27); 7,4438 (1,45); 7,4228 (0,6); 7,4182 (0,67); 7,4048 (1,11); 7,4002 (1,09); 7,3854 (0,66); 7,3804 (0,71); 7,375 (0,71); 7,371 (0,68); 7,3565 (1,21); 7,3528 (1,22); 7,3383 (0,63); 7,3348 (0,57); 7,3038 (1,77); 7,2991

4-chlor-2- (1,19); 7,2848 (1,87); 7,2808 (0,94); 4,3274 (4,62);

3,334 (88,25); 2,5416 (3,24); 2,5247 (0,52); 2,5199

(trifluormethyl)- (0,86); 2,5113 (10,97); 2,5068 (21,94); 2,5023 (28,77);

20-268 2-chlor-phenyl phenyl 0 CH3 C(CH3)3 H 2,4976 (20,67); 2,4931 (9,77); 1,4282 (16)

Verbindung Nr. 20-269, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6857 (1,94); 8,6727 (3,73); 8,6592 (2,07); 7,8522 (6,96); 7,8473 (7,4); 7,7172 (3,44); 7,7125 (3,34); 7,6951 (4,04); 7,6908 (3,78); 7,5288 (0,42); 7,5083 (3,49); 7,5065 (3,46); 7,4887 (8,2); 7,4686 (3,2); 7,4626 (3,7); 7,4525 (4,23); 7,4464 (5,98); 7,4271 (5,41); 7,4167 (16); 7,4091 (10,21); 7,4053 (7,4); 7,3928 (8,94); 7,3734 (1,47); 7,3703 (1,25); 4,3369 (5,95); 4,3229 (12,79); 4,3089 (6,3); 3,6904 (3,27); 3,6766 (9,28); 3,6627 (9,21); 3,6487 (3,32); 3,3427 (315,93);

2-chlor-4- 2,6831 (0,55); 2,6786 (0,74); 2,6742 (0,54); 2,5488

(34,74); 2,5316 (2,2); 2,5182 (45,59); 2,514 (87,75);

(trifluomiethyl)- 2,5095 (112,19); 2,505 (80,97); 2,5008 (39,04); 2,3406

20-269 2-chlor-phenyl phenyl 0 CH2 CH2 H (0,54); 2,3363 (0,72); 2,3318 (0,51)

Verbindung Nr. 20-270, Solvent: [DMSO], Spektrometer:

2-chlor-4- 399.95MHz-.8,4764 (1,47); 8,4475 (1,24); 8,4427

(1,34); 8,4355 (1,34); 8,4306 (1,3); 7,8548 (1,23);

(trifluormethyl)- 7,8501 (1,31); 7,7675 (1,21); 7,7626 (1,26); 7,7487

20-270 2-chlor-3-pyridyl phenyl 0 CH2 C(CH3)2 H (1,46); 7,7438 (1,36); 7,7116 (0,6); 7,7074 (0,58);

Physikalische Daten: ¹ H-NMR, δ [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

7,6899 (0,7); 7,6856 (0,64); 7,4828 (1,42); 7,4707 (1,36); 7,464 (1,26); 7,452 (1,26); 7,3672 (1,08); 7,3458 (0,98); 4,3787 (4,52); 3,3653 (0,55); 3,3409 (148,83); 3,3119 (0,32); 2,5479 (11,64); 2,5311 (0,78); 2,5262 (1,26); 2,5177 (17,1); 2,5132 (34,25); 2,5086 (44,74); 2,504 (31,94); 2,4994 (15,06); 1,4803 (16)

Verbindung Nr. 20-271, Solvent: [DMSO], Spektrometer: 399.95MHz8,4494 (1,21); 8,4445 (1,43); 8,4372 (2,53); 8,4327 (1,95); 7,7322 (1,1); 7,7273 (1,17); 7,7225 (0,64); 7,7136 (1,72); 7,7086 (1,31); 7,7003 (0,53); 7,6939 (1,04); 7,6841 (1,8); 7,6778 (1,03); 7,4939 (1,25); 7,4818 (1,23); 7,4751 (1,11); 7,4631 (1,08); 7,3181 (1,17); 7,296 (1,05); 4,3297 (4,57); 3,389 (0,32);

4-chlor-2- 3,3418 (213,36); 2,6825 (0,32); 2,6778 (0,43); 2,5481

(12,03); 2,5311 (1,11); 2,5177 (25,37); 2,5133 (50,43);

(trifluormethyl)- 2,5087 (65,7); 2,5042 (47,42); 2,4997 (22,66); 2,3355

20-271 2-chlor-3-pyridyl phenyl 0 CH3 C(CH3)3 H (0,42); 1,4395 (16)

Verbindung Nr. 20-272, Solvent: [DMSO], Spektrometer: 399.95MHz

8,8792 (2,37); 8,8659 (4,61); 8,8525 (2,5); 8,4849 (8,31); 8,4801 (8,81); 8,4728 (8,86); 8,468 (8,62); 7,8861 (8,63); 7,8812 (8,68); 7,8672 (9,98); 7,8623 (9,87); 7,8554 (8,82); 7,8504 (9,33); 7,72 (4,26); 7,7157 (4,14); 7,6983 (4,97); 7,694 (4,66); 7,5199 (9,72); 7,5079 (9,4); 7,5011 (8,86); 7,489 (8,68); 7,4161 (8,03); 7,3943 (7,08); 4,3399 (7,49); 4,3261 (16); 4,3124 (7,96); 3,7093 (4,15); 3,6956 (11,68); 3,6818 (11,56); 3,668 (4,17); 3,4539 (0,33); 3,4505 (0,33); 3,4276 (0,49); 3,4064 (0,79); 3,3451 (1017,79); 3,2868 (0,37); 2,8964 (0,36); 2,6873 (0,59); 2,683 (1,26); 2,6784 (1,71); 2,6739 (1,22); 2,6693 (0,58); 2,5486 (16,11); 2,5318 (4,86); 2,5269 (7,6); 2,5184 (98,26); 2,5139

2-chlor-4- (197,2); 2,5094 (258,78); 2,5048 (185,74); 2,5003

(87,65); 2,3452 (0,57); 2,3407 (1,21); 2,3361 (1,67);

(trifluorniethyl)- 2,3315 (1,18); 2,327 (0,53); 1,4402 (0,75); 1,2417

20-272 2-chlor-3-pyridyl phenyl 0 CH2 CH2 H (0,71)

Verbindung Nr. 20-273, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2809 (1,54); 7,8447 (1,31); 7,8399 (1,4); 7,7027 (0,64); 7,6985 (0,62); 7,6808 (0,74); 7,6769 (0,7);

2-chlor-4- 7,6167 (1,04); 7,6147 (1,11); 7,5972 (1,23); 7,5948

(1,24); 7,4108 (0,4); 7,408 (0,45); 7,3922 (1,17); 7,3895

(trifluormethyl)- (1,18); 7,3738 (0,96); 7,3708 (0,91); 7,3529 (1,17);

20-273 2-brom-phenyl phenyl 0 CH2 C(CH3)2 H 7,3375 (0,79); 7,3327 (1,78); 7,3184 (0,86); 7,3136

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

(1,1); 7,2991 (0,45); 7,2945 (0,49); 7,2874 (1,27); 7,2829 (1,06); 7,269 (0,91); 7,2646 (0,79); 4,3772 (4,64); 3,335 (156,03); 2,5416 (8,9); 2,5246 (0,84); 2,5111 (18,12); 2,5068 (36,48); 2,5023 (47,97); 2,4977 (35,24); 2,4934 (17,29); 1,4716 (16)

Verbindung Nr. 20-274, Solvent: [DMSO], Spektrometer: 399.95MHz

8,2393 (1,48); 7,7135 (0,56); 7,7069 (0,77); 7,6914 (0,51); 7,6849 (1,05); 7,6751 (1,83); 7,6687 (1,05); 7,6235 (1,07); 7,6209 (1,1); 7,6037 (1,28); 7,601 (1,24); 7,4195 (0,44); 7,4166 (0,46); 7,4009 (1,23); 7,3981 (1,19); 7,3824 (0,95); 7,3794 (0,86); 7,3391 (0,73); 7,3345 (0,9); 7,3199 (0,92); 7,3151 (1,08); 7,3026 (1,28); 7,2961 (0,57); 7,2809 (1, 1); 7,2727 (1,29);

4-chlor-2- 7,2682 (1,13); 7,2541 (0,98); 7,2497 (0,84); 4,3258

(4,59); 3,33 (70,11); 2,5413 (4,54); 2,5244 (0,61);

(trifluormethyl)- 2,5194 (1); 2,511 (11,91); 2,5066 (23,51); 2,502

20-274 2-brom-phenyl phenyl 0 CH3 C(CH3)3 H (30,42); 2,4974 (21,73); 2,4929 (10,21); 1,432 (16)

Verbindung Nr. 20-275, Solvent: [DMSO], Spektrometer: 399.95MHz8,677 (2,32); 8,6636 (4,57); 8,6502 (2,43); 7,8463 (8,39); 7,8412 (8,99); 7,7114 (4,09); 7,707 (3,93); 7,6897 (4,78); 7,6851 (4,47); 7,6549 (7,91); 7,6372 (7,44); 7,6348 (8,35); 7,5254 (0,43); 7,5213 (0,43); 7,4501 (2,27); 7,4474 (2,48); 7,4294 (6,83); 7,4133 (9); 7,4103 (12,89); 7,3878 (11,85); 7,3846 (16); 7,3752 (7,87); 7,3699 (7,93); 7,3648 (4,67); 7,3559 (6,33); 7,3524 (4,66); 7,351 (4,86); 7,3381 (3,37); 7,333 (2,86); 4,3298 (7,14); 4,3157 (15,6); 4,3017 (7,58); 3,6763 (3,91); 3,6624 (11,22); 3,6485 (11,13); 3,6344 (3,96); 3,3287 (262,97); 2,6755 (0,84); 2,671 (1,17); 2,6665 (0,85); 2,6623 (0,41); 2,5413 (42,54); 2,5243

2-chlor-4- (3,43); 2,5109 (67,35); 2,5065 (134,61); 2,5019

(176,63); 2,4974 (127,79); 2,4929 (61,18); 2,3331

(trifluormethyl)- (0,81); 2,3287 (1,13); 2,3242 (0,82); 2,32 (0,39); 1,2349

20-275 2-brom-phenyl phenyl 0 CH2 CH2 H (0,51); -0,0002 (1,21)

Verbindung Nr. 20-276, Solvent: [DMSO], Spektrometer: 399.95MHz8,6012 (1,54); 8,5878 (2,91); 8,5747 (1,48); 7,7241 (2,52); 7,7176 (3,13); 7,7019 (2,67); 7,6953 (3,8); 7,6718 (7,26); 7,665 (5,72); 7,6608 (3,61); 7,6577 (5,54); 7,6428 (2,43); 7,6372 (4,91); 7,4531 (1,79);

4-chlor-2- 7,4502 (1,88); 7,4342 (5,7); 7,4297 (2,72); 7,416 (4,43);

7,4131 (4,07); 7,3762 (7,14); 7,3721 (6,99); 7,3533

(trifluormethyl)- (16); 7,336 (5,64); 7,3336 (5,34); 4,2828 (4,61); 4,2682

20-276 2-brom-phenyl phenyl 0 CH2 CH2 H (10,25); 4,2537 (4,86); 3,627 (2,58); 3,6128 (7,24);

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

2,6707 (1,41); 2,6661 (1,06); 2,6616 (0,53); 2,5411 (15,33); 2,5241 (3,55); 2,5193 (5,45); 2,5107 (76,72); 2,5062 (160,49); 2,5017 (217,15); 2,4971 (161,5); 2,4926 (81,83); 2,4746 (16); 2,3375 (0,47); 2,333 (1,01); 2,3284 (1,41); 2,3238 (1,07); 2,3194 (0,54); 1,2349 (0,58); -0,0002 (1,24)

Verbindung Nr. 20-280, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5626 (2,47); 8,5492 (4,83); 8,5357 (2,45); 7,8878 (7,67); 7,8857 (8,04); 7,8681 (8,38); 7,8659 (8,19); 7,7257 (3,93); 7,7192 (4,93); 7,7035 (4,13); 7,697 (6); 7,6738 (11,36); 7,6672 (8,19); 7,4604 (3,7); 7,4577 (3,9); 7,4416 (8,42); 7,4389 (8,59); 7,4229 (5,46); 7,4202 (5,36); 7,3724 (8,27); 7,3501 (7,31); 7,2915 (7,43); 7,2874 (8,23); 7,2725 (6,4); 7,2684 (6,24); 7,1869 (4,84); 7,1827 (4,64); 7,1675 (6,98); 7,1633 (6,64); 7,1487 (4,16); 7,1444 (3,82); 4,2868 (7,05); 4,272 (16); 4,2574 (7,56); 3,6165 (3,93); 3,6021 (11,13); 3,5878 (10,73); 3,5732 (3,52); 3,3274 (257,7); 2,68 (0,37); 2,6754 (0,77); 2,6709 (1,05); 2,6663 (0,76); 2,6617 (0,36); 2,5412 (31,49); 2,5243 (3,27); 2,5108

4-chlor-2- (61,88); 2,5064 (122,47); 2,5018 (159,53); 2,4972

(114,77); 2,4927 (54,57); 2,3374 (0,36); 2,3332 (0,75);

(trifluormethyl)- 2,3286 (1,02); 2,324 (0,75); 2,3195 (0,34); 1,2345

20-280 2-iod-phenyl phenyl 0 CH2 CH2 H (0,55); -0,0002 (1,3)

Verbindung Nr. 20-281, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3635 (1,54); 7,8522 (1,32); 7,8472 (1,39); 7,7467 (0,85); 7,7273 (1,15); 7,7043 (1); 7,6842 (1,6); 7,667 (0,7); 7,6262 (0,68); 7,6073 (0,86); 7,4188 (1,02);

2-chlor-4- 7,4002 (0,89); 7,3415 (1,16); 7,3197 (1,06); 4,3633

(4,65); 3,33 (87,86); 2,5413 (8,46); 2,5243 (0,75);

2-(trifluormethyl)- (trifluormethyl)- 2,5109 (16,03); 2,5065 (31,63); 2,502 (41,16); 2,4974

20-281 phenyl phenyl 0 CH2 C(CH3)2 H (29,71); 2,493 (14,23); 1,4551 (16)

Verbindung Nr. 20-282, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3145 (1,55); 7,7476 (0,88); 7,7282 (1,17); 7,7138 (0,75); 7,7085 (1,12); 7,6925 (1,45); 7,6868 (1,33); 7,6776 (2,09); 7,6718 (1,67); 7,6261 (0,67); 7,6071 (0,87); 7,588 (0,33); 7,4014 (1,03); 7,3827 (0,9); 7,29

4-chlor-2- (1,2); 7,2679 (1,09); 4,3083 (4,63); 3,3349 (172,86);

3,303 (0,4); 2,6711 (0,34); 2,5414 (1,3); 2,5244 (0,91);

2-(trifluormethyl)- (trifluormethyl)- 2,511 (19,6); 2,5066 (39,33); 2,5021 (51,72); 2,4975

20-282 phenyl phenyl 0 CH3 C(CH3)3 H (37,59); 2,493 (18,2); 2,3288 (0,33); 1,4166 (16)

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder CAS- bzw.

Bsp.-Nr. Q X L ¹ L ² L ³ Y Patent-Nr.

Verbindung Nr. 20-283, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7712 (2,51); 8,7579 (4,81); 8,7445 (2,57); 7,8548 (8,92); 7,8495 (9,08); 7,7923 (5,96); 7,7729 (7,94); 7,7473 (2,59); 7,7294 (7,2); 7,7177 (4,73); 7,711 (5,61); 7,7004 (5,27); 7,6961 (4,6); 7,684 (0,58); 7,6701 (4,72); 7,6511 (5,98); 7,6323 (2,18); 7,525 (7,22); 7,5062 (5,96); 7,4045 (7,99); 7,3829 (7,03); 4,3181 (7,51); 4,3042 (16); 4,2903 (7,8); 3,6854 (4,15); 3,6716 (11,54); 3,6577 (11,37); 3,6438 (4,1); 3,4387 (0,43); 3,3454 (879,81); 2,6867 (0,57); 2,6823 (1,18); 2,6777 (1,58); 2,6731 (1,13); 2,6686 (0,54); 2,548 (79,94);

2-chlor-4- 2,531 (5,04); 2,5176 (93,91); 2,5132 (182,99); 2,5086

2-(trifluormethyl)- (trifluormethyl)- (236,55); 2,504 (168,8); 2,4995 (79,54); 2,3444 (0,54);

2,3399 (1,1); 2,3353 (1,51); 2,3308 (1,07); 2,3263

20-283 phenyl phenyl 0 CH2 CH2 H (0,49); 1,2406 (0,61)

Verbindung Nr. 20-284, Solvent: [DMSO], Spektrometer: 399.95MHz, δ, 8,76 (t, 1H, NH), 7,81 - 7,62 (m, 4H),

2-(trifluormethyl)- 4-(trifluormethyl)- 7,50 (d, 1H), 7,15 (d, 2H), 4,18 (t, 2H), 3,65 - 3,61 (q,

2H).

20-284 phenyl phenyl 0 CH2 CH2 H

Tabelle 21

Verbindungen der Formel 1-21

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

21-1 3 -methyl-2-thienyl CH2 CH2 - H

21-2 2,4-dichlor-phenyl CH2 CH2 CH2 H WO-A 2008/101976

21-3 4-chlor-phenyl CH2 CH2 - H

21-4 2,4-dichlor-phenyl CH2 CH2 - H WO-A 2007/108483

21-5 4-chlor-phenyl CH(OCH3) CH(CH3) - H

21-6 2,4-dichlor-phenyl CH(OCH3) CH(CH3) - H

21-7 4-chlor-phenyl CH(CH3) CH2 - H

21-8 2,4-dichlor-phenyl CH(CH3) CH2 - H

21-9 4-chlor-phenyl CH2 CH(CH3) - H

21-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

21-11 4-chlor-phenyl C(CH3)2 CH2 - H

21-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H

21-13 2-chlor-phenyl CH2 CH2 - H

21-14 3 ,4-dichlor-phenyl CH2 CH2 - H

21-15 3,5- dichlor-pheny 1 CH2 CH2 - H

21-16 3-chlor-phenyl CH2 CH2 - H

21-17 2-fluor-phenyl CH2 CH2 - H

21-18 2,6-difluor-phenyl CH2 CH2 - H

21-19 2,6-dichlor-phenyl CH2 CH2 - H

21-20 3 -(trifluormethyl)-phenyl CH2 CH2 - H

21-21 4-(trifluormethyl)-phenyl CH2 CH2 - H

21-22 2-methyl-phenyl CH2 CH2 - H

21-23 2,4,6-trimethyl-phenyl CH2 CH2 - H

21-24 3 ,4-bismethoxy-phenyl CH2 CH2 - H

21-25 phenyl CH2 CH2 - H

21-26 4-chlor-phenyl C(CH2-CH2) CH2 - H

21-27 2,4-dichlor-phenyl C(CH2-CH2) CH2 - H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

21-28 4-chlor-phenyl CH2 C(CH2-CH2) - H

21-29 2,4-dichlor-phenyl CH2 C(CH2-CH2) - H

21-30 4-chlor-phenyl 0 CH2 CH2 H

21-31 2,4-dichlor-phenyl 0 CH2 CH2 H

21-32 4-chlor-phenyl CH2 CH2 CH2 H

21-33 4-chlor-phenyl NCH3 CH2 CH2 H

21-34 2,4-dichlor-phenyl NCH3 CH2 CH2 H

21-35 4-chlor-phenyl CH(OCH3) CH2 - H

21-36 2,4-dichlor-phenyl CH(OCH3) CH2 - H

21-37 2-thienyl CH2 CH2 - H

21-38 3-thienyl CH2 CH2 - H

21-39 2-furyl CH2 CH2 - H

21-40 3-furyl CH2 CH2 - H

21-41 phenyl CH2 CH2 CH(CH3) H

21-42 phenyl CH2 CH2 CH2 H

21-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

21-44 4-t-butyl-phenyl CH2 CH2 CH2 H

21-45 4-methyl-phenyl CH2 CH2 CH2 H

21-46 phenyl CH2 CH2 CH(CH2CH3) H

21-47 2-methoxy-phenyl CH2 CH2 CH2 H

21-48 2-methyl-phenyl CH2 CH2 CH2 H

21-49 3 -methyl-phenyl CH2 CH2 CH2 H

21-50 3-chlor-phenyl CH2 CH2 CH2 H

21-51 2,6-difluor-phenyl CH2 CH2 CH2 H

21-52 4-chlor-phenyl CH2 CH2 CH2 H

21-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

21-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

21-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

21-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

21-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

21-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

21-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

21-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

21-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

21-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

21-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

21-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

21-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

21-66 4-phenoxy-phenyl CH2 CH2 CH2 H

21-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

21-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

21-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

21-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

21-71 4-methoxy-phenyl CH2 CH2 CH2 H

21-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

21-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

21-74 4-fluor-phenyl CH2 CH2 CH2 H

21-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

21-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

21-77 2-chlor-phenyl CH2 CH2 CH2 H

21-78 4-chlor-phenyl CH2 CH(CH3) - cyclopropyl

Tabelle 22

Verbindungen der Formel 1-22

1-22

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder

Bsp.-Nr. 0 X L ¹ L ² L ³ Y Quelle

IH-NMR (d6-DMSO): δ [ppm], 10,10 (s, 1H, NH), 7.76 (d, 1H), 7,38 - 7,32 (dd, 4H), 7,05 (d, 1H). 3,91 - 3,74 (2xm, 2H), 3.37 - 3,30 (m. 1 H), 1 ,33 (d, 3H).

22-1 3-chlor-thienyl 4-chlor-phenyl CH(CH3) CH2 H

'H-NMR (d6-DMSO): δ [ppm], 10, 15 (s, 1H,

NH), 7,76 (d, 1H), 7,57 - 7,41 (m, 3H), 7,05 (d, 1H), 3,98 - 3,79 (m, 3H), 3,37 - 3,30 (m, 1H),

22-2 3-chlor-thienyl 2,4-dichlor-phenyl CH(CH3) CH3 H 1 ,30 (d, 3H).

Tabelle 23

Verbindungen der Formel 1-23

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

23-1 3 -methyl-2-thienyl CH2 CH2 - H

23-2 2,4-dichlor-phenyl CH2 CH2 CH2 H

Verbindung Nr. 23-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4094 (1 ,95); 8,3977 (3,36); 8,3841 (1 ,84); 7,3599 (7,78); 7,34 (12,6); 7,2746 (12,92); 7,262 (15,69); 7,2601 (16); 7,2543

23-3 4-chlor-phenyl CH2 CH2 H (8,56); 3,441 (3); 3,4243 (6,9); 3,4086

Physikalische Daten: 'H-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

2,4933 (46,1 1 ); 2,4671 (0,33); 2,3679 (0,73); 2,3336 (0,59); 2,329 (0,81 ); 2,3245 (0,59); 2,0745 (0,51 ); 1 ,2203 (13,97); 1 ,2028 (13,7); -0,0002 (8,06)

Verbindung Nr. 23-8, Solvent: [DMSO], Spektrometer: 399.95MHz

20,0115 (0,42); 8,4185 (1 ,14); 8,4043 (2,34); 7,5676 (6,37); 7,5623 (6,93); 7,4672 (3,41 ); 7,446 (8, 13); 7,4197 (4,9); 7,4144 (4,67); 7,3987 (2, 12); 7,3933 (2,08); 7,2215 (16); 3,5268 (0,91 ); 3,5095 (2,03); 3,4925 (2,41 ); 3,4749 (2,34); 3,4598 (1 ,59); 3,4424 (2,42); 3,4267 (2,78); 3,4105 (1 ,85); 3,3964 (2,57); 3,3792 (3,85); 3,3646 (7,87); 3,3322 (2494,64); 3,2606 (1 ,24); 2,71 1 1 (1 ,91 ); 2,6755 (4,55); 2,6709 (6,21 ); 2,6664 (4,54); 2,5412 (475,91 ); 2,5242 (23,84); 2,5109 (365,49); 2,5064 (724,17); 2,5019 (947); 2,4973 (685,77); 2,4929 (333,49); 2,3674 (1 ,83); 2,3331 (4,33); 2,3286 (5,98); 2,3241 (4,36); 2,2901 (0,62); 2,0742 (1 ,94); 1 ,2585 (0,47); 1 ,2351 (1 ); 1 ,2128 (13,29); 1 ,196 (13,12); 0,008

23-8 2,4-dichlor-phenyl CH(CH3) CH2 H (1 ,33); -0,0001 (31 ,97); -0,0083 (0,96)

23-9 4-chlor-phenyl CH2 CH(CH3) - H

23-10 2,4-dichlor-phenyl CH2 CH(CH3) - H

Verbindung Nr. 23-12, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1803 (0,4); 8,1644 (0,81 ); 8,1492 (0,41 ); 7,5252 (2,25); 7,5195 (2,43); 7,4713 (1 ,46); 7,4496 (2,2); 7,3726 (1 ,46); 7,3667 (1 ,39); 7,351 (0,97); 7,3452 (0,92); 7,1644 (5,38); 3,7449 (2,75); 3,729 (2,72); 3,3766 (0,59); 3,3352 (262,2); 2,6755 (0,4); 2,671 1 (0,56); 2,6669 (0,41 ); 2,5415 (52,18); 2,5244 (1 ,83); 2,51 1 (32,18); 2,5067 (65,15); 2,5021 (86,34); 2,4976 (63,79); 2,4932 (31 ,7); 2,3334 (0,38); 2,3289 (0,52); 2,3244 (0,38); 2,0742

23-11 4-chlor-phenyl C(CH3)2 CH2 H (0,36); 1 ,4397 (16); -0,0002 (3,1 )

Verbindung Nr. 23-13, Solvent: [DMSO],

23-12 2,4-dichlor-phenyl C(CH3)2 CH2 - H Spektrometer: 399.95MHz

Physikalische Daten: 'H-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

8,5227 (0,93); 8,5081 (1,73); 8,4939 (0,91); 7,3651 (0,56); 7,3482 (1,24); 7,3442 (1,11); 7,3273 (2,36); 7,3102 (1,17); 7,3065 (1,52); 7,2897 (0,7); 7,2308 (16); 7,1022 (0,48); 7,0901 (3,28); 7,0702 (5,22); 7,0591 (0,71); 7,0501 (2,73); 7,0374 (0,36); 3,4202 (1,99); 3,4034 (4,4); 3,3873 (4,77); 3,3698 (4,01); 3,342 (300,48); 3,2921 (0,49); 2,8849 (2,46); 2,8675 (4,61); 2,85 (2,18); 2,6763 (0,54); 2,6718 (0,75); 2,6674 (0,55); 2,542 (4,42); 2,525 (2,8); 2,5118 (45,29); 2,5073 (89,72); 2,5028 (117,31); 2,4982 (85,04); 2,4937 (41 ,62); 2,3338 (0,53); 2,3295 (0,73); 2,3248 (0,55); -0,0002 (0,86)

Verbindung Nr.23-19, Solvent: [DMSO], Spektrometer: 399.95MHz

19,1408 (0,92); 8,5291 (1,11); 7,4714 (4,01); 7,4516 (5,66); 7,3073 (1,97); 7,2832 (6,17); 7,2679 (0,98); 4,87 (1,07); 4,3055 (0,96); 4,1606 (1,02); 3,7688 (1,03); 3,7288 (0,93); 3,679 (0,98); 3,6295 (1,15); 3,6029 (1 ,58); 3,562 (1 ,5); 3,5478 (1 ,61 ); 3,5279 (2,65); 3,4948 (2,73); 3,4749 (2,51); 3,4383 (7); 3,426 (6,9); 3,3432 (6877,18); 3,2793 (8,44); 3,2304 (3,47); 3,1713(1,12); 3,1518 (2,19); 3, 1353 (3, 17); 3, 1176 (2,28); 3,0968 (1 ,28); 3,0709 (1 ,46); 3,0604 (0,99); 3,0447 (1 ,06); 3,0289 (0,95); 2,9409 (1,13); 2,9204 (1,01); 2,9094 (0,93); 2,676 (11,25); 2,6716 (16); 2,6673 (11,67); 2,5964 (1,82); 2,5418 (69,55); 2,5246 (57,73); 2,5113 (953,34); 2,507 (1877,51 ); 2,5026 (2445,77); 2,4981 (1776,72); 2,4938 (872,51); 2,4384 (2,36); 2,391 (1,34); 2,3673 (1,3); 2,3339 (10,71); 2,3293 (14,87); 2,3247 (10,66); 2,2914 (1 ,5); 2,0737 (7, 17); 1 ,2978 (0,92); 1 ,258 (1,34); 1,2356 (1,54); 0,008 (2,92); -0,0002

23-17 2-fluor-phenyl CH2 CH2 H (64,72); -3,221 (0,96); -3,6597 (0,89)

Verbindung Nr.23-20, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4219 (1,19); 8,4085 (2,09); 8,3958

23-18 2,6-difluor-phenyl CH2 CH2 H (1,11); 7,5895 (4,83); 7,5614 (8,2); 7,5514

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

Verbindung Nr. 23-23, Solvent: [DMSO], Spektrometer: 399.95MHz8,5693 (0,36); 8,5553 (0,7); 8,5404 (0,34); 7,347 (5,6); 6,8086 (3,84); 3,332 (151 ,28); 3,331 (153,07); 3,2272 (0,51 ); 3,2132 (0,83); 3,2085 (0,68); 3, 1993 (0,82); 3, 1923 (0,66); 3,1855 (0,88); 3, 1717 (0,57); 2,7881 (1 ,05); 2,7749 (0,77); 2,7669 (1 ,01 ); 2,7613 (0,8); 2,7471 (0,84); 2,6753 (0,45); 2,6708 (0,63); 2,6664 (0,45); 2,5412 (3,48); 2,524 (2,48); 2,5108 (37); 2,5063 (73,94); 2,5018 (96,97); 2,4972 (69,95); 2,4926 (33,72); 2,3331 (0,46); 2,3285 (0,63); 2,3238 (0,46); 2,2873 (16);

23-21 4-(trifluormethyl)-phenyl CH2 CH2 H 2, 181 1 (6,78); -0,0002 (5,92)

Verbindung Nr. 23-25, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4296 (0,87); 8,4161 (1 ,52); 8,4022 (0,85); 7,32 (2,13); 7,3161 (0,95); 7,3017 (5,36); 7,2883 (1 ,9); 7,2836 (5,53); 7,2716 (16); 7,251 1 (4,62); 7,2472 (7,01 ); 7,2419 (1 ,67); 7,2277 (4,16); 7,21 14 (1 ,12); 7,2062 (2,81 ); 7,2005 (0,7); 7,1921 (0,62); 7, 1884 (0,99); 7,1849 (0,5); 3,4471 (2); 3,4294 (3,2); 3,415 (3,12); 3,4108 (3,25); 3,3959 (2,24); 3,3378 (122,84); 3,3346 (136,02); 3,3327 (135,44); 2,8256 (3,4); 2,8065 (4,9); 2,7886 (3,03); 2,6756 (0,49); 2,671 1 (0,66); 2,6665 (0,49); 2,5414 (12,22); 2,5242 (2,74); 2,51 1 (39,9); 2,5065 (79,55); 2,502 (104,35); 2,4974 (75,24); 2,4928 (36,63); 2,3334 (0,48); 2,3287 (0,66); 2,324 (0,47); 2,074 (0,46); -

23-22 2-methyl-phenyl CH2 CH2 H 0,0002 (6,1 1 )

Verbindung Nr. 23-12, Solvent: [DMSO], Spektrometer: 399.95MHz

8, 1803 (0,4); 8,1644 (0,81 ); 8,1492 (0,41 ); 7,5252 (2,25); 7,5195 (2,43); 7,4713 (1 ,46); 7,4496 (2,2); 7,3726 (1 ,46); 7,3667 (1 ,39); 7,351 (0,97); 7,3452 (0,92); 7,1644 (5,38); 3,7449 (2,75); 3,729 (2,72); 3,3766 (0,59); 3,3352 (262,2); 2,6755 (0,4); 2,671 1 (0,56); 2,6669 (0,41 ); 2,5415 (52,18); 2,5244 (1 ,83); 2,51 1 (32,18);

23-23 2,4,6-trimethyl-phenyl CH2 CH2 H 2,5067 (65,15); 2,5021 (86,34); 2,4976

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

(63,79); 2,4932 (31,7); 2,3334 (0,38); 2,3289 (0,52); 2,3244 (0,38); 2,0742 (0,36); 1,4397 (16); -0,0002 (3,1)

Verbindung Nr.23-13, Solvent: [DMSO],

Spektrometer: 399.95MHz

15,3304 (0,91); 14,7843 (0,89); 8,4566

(1.23) ; 8,4447 (1,06); 7,8866 (0,91); 7,442 (2,27); 7,4235 (2,45); 7,4186 (2,68); 7,3595 (1,83); 7,3415 (2,82); 7,3077 (1,14); 7,2929 (2,85); 7,2887 (2,2); 7,2751 (14,86); 7,2598 (2,02); 7,2538 (1,87); 3,9437 (0,86); 3,7152 (1,16); 3,7111 (1,12); 3,6657 (1 ,33); 3,6279 (0,97); 3,6084 (1,08); 3,5888 (1,4); 3,5481 (1,58); 3,5292 (1,71); 3,4739 (3,46); 3,4572 (4,98); 3,4396 (5,96); 3,4243 (5,58); 3,3369 (4888,75); 3,2607 (2,51); 3,2253 (1 ,62); 3,2208 (1 ,54); 3,2035 (1 ,25); 3,1766 (0,88); 3,1355 (1,06); 3,0607 (1,03); 2,9574 (2,89); 2,9401 (4,58); 2,9213 (2,47); 2,7494 (1,02); 2,7109 (1,79); 2,6756(11,72); 2,6711 (16); 2,6665 (11,63); 2,6487 (1,41); 2,6168 (1,28); 2,5979 (1,95); 2,5922 (1,93); 2,5414 (434,46); 2,5245 (53,58); 2,5111 (966,23); 2,5067 (1928,89); 2,5021 (2522,35); 2,4975 (1818,19); 2,493 (878,69); 2,4235

(1.24) ; 2,3848 (0,93); 2,3676 (1 ,3); 2,3334 (11 ,4); 2,3289 (15, 19); 2,3244 (11 ,05); 2,2907 (1,19); 2,0739 (8,74); 1,4393 (0,91); 1,258 (1,52); 1,2445 (1,31); 1,2354 (2,36); 0,0079 (1,5); -0,0002 (37,15); -

23-24 3,4-bismethoxy-phenyl CH2 CH2 H 3,2871 (0,87)

Verbindung Nr 23-14, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4017 (1,01); 8,3886 (1,96); 8,3744 (1,08); 7,7614 (0,52); 7,5594 (5,74); 7,5492 (0,49); 7,5389 (6,81); 7,5281 (5,8); 7,5232 (5,72); 7,2553 (3,23); 7,2503

(3,09): 7,2382 (16); 7,2297 (2,73); 3,4901 (0,39): 3,4648 (2,16); 3,4478 (5,1); 3,4331 (5,43); 3,4161 (2,82); 3,3398 (844,78);

3,2759 (1,01); 3,2373 (0,37); 3,1759 (0,33); 2,8477 (0,4); 2,8323 (3,6); 2,8151

23-25 phenyl CH2 CH2 H (7,12); 2,7978 (3,15); 2,7117 (1,08);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

23-38 3-thienyl CH2 CH2 - H

23-39 2-furyl CH2 CH2 - H

23-40 3-furyl CH2 CH2 - H

23-41 phenyl CH2 CH2 CH(CH3) H

23-42 phenyl CH2 CH2 CH2 H

23-43 2-Cl-phenyl CH2 CH2 CH(CH3) H

23-44 4-t-butyl-phenyl CH2 CH2 CH2 H

23-45 4-methyl-phenyl CH2 CH2 CH2 H

23-46 phenyl CH2 CH2 CH(CH2CH3) H

23-47 2-methoxy-phenyl CH2 CH2 CH2 H

23-48 2-methyl-phenyl CH2 CH2 CH2 H

23-49 3 -methyl-phenyl CH2 CH2 CH2 H

23-50 3-chlor-phenyl CH2 CH2 CH2 H

23-51 2,6-difluor-phenyl CH2 CH2 CH2 H

23-52 4-chlor-phenyl CH2 CH2 CH2 H

23-53 2,6-dichlor-phenyl CH2 CH2 CH(CH3) H

23-54 3,5- dichlor-pheny 1 CH2 CH2 CH(CH3) H

23-55 2,6-dimethyl-phenyl CH2 CH2 CH2 H

23-56 2,5-dichlor-phenyl CH2 CH2 CH2 H

23-57 4-i-propoxy-phenyl CH2 CH2 CH2 H

23-58 3 -trifluormethyl-phenyl CH2 CH2 CH(CH3) H

23-59 4-methyl-phenyl CH2 CH2 CH(CH3) H

23-60 2-methyl-phenyl CH2 CH2 CH(CH3) H

23-61 3 ,4-dichlor-phenyl CH2 CH2 CH(CH3) H

23-62 3,5- dichlor-pheny 1 CH2 CH2 CH2 H

23-63 2,6-dimethyl-phenyl CH2 CH2 CH(CH3) H

23-64 4-trifluormethyl-phenyl CH2 CH2 CH(CH3) H

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

23-65 2,5-dichlor-phenyl CH2 CH2 CH(CH3) H

23-66 4-phenoxy-phenyl CH2 CH2 CH2 H

23-67 3-chlor-phenyl CH2 CH2 CH(CH3) H

23-68 4-phenoxy-phenyl CH2 CH2 CH(CH3) H

23-69 2,4-dichlor-phenyl CH2 CH2 CH(CH3) H

23-70 2-difluormethoxy-phenyl CH2 CH2 CH(CH3) H

23-71 4-methoxy-phenyl CH2 CH2 CH2 H

23-72 4-chlor-phenyl CH2 CH2 CH(CH3) H

23-73 4-chlor-phenyl CH2 CH2 CH(i-propyl) H

23-74 4-fluor-phenyl CH2 CH2 CH2 H

23-75 4-chlor-phenyl CH2 CH2 CH(n-propyl) H

23-76 4-chlor-phenyl CH2 CH2 CH(t-butyl) H

23-77 2-chlor-phenyl CH2 CH2 CH2 H

Verbindung Nr.23-78, Solvent: [DMSO], Spektrometer: 399.95MHz8,5276 (1,42); 8,5134 (2,6); 8,4994 (1,44); 7,4844 (5,04); 7,4793 (2,2); 7,4681 (3,4); 7,4628 (14,97); 7,4396 (11,51); 7,418 (4,25); 7,3903 (0,52); 7,1454 (16); 4,0563 (1,04); 4,0384 (3,55); 4,0207 (3,69); 4,0141 (1,46); 4,0026 (1,91); 3,9903 (1,1); 3,9757 (1,03); 3,9666 (0,39); 3,8754 (1,03); 3,8618 (1 ,75); 3,8479 (1,12); 3,8413 (1 ,72); 3,8277 (2,63); 3,8139 (1,32); 3,7372 (1 ,46); 3,7211 (1 ,66); 3,7147 (1 ,44); 3,7029 (1 ,39); 3,6988 (1 ,57); 3,6872 (1,08); 3,6805 (0,98); 3,6645 (0,84); 3,3233 (20,51); 2,6714 (0,38); 2,5247 (1 ,29); 2,5111 (22,28); 2,5069 (43,47); 2,5024 (56,41); 2,4979 (41,12); 2,4936 (20,4); 2,3292 (0,35); 1 ,9894 (11 ,92); 1,3361 (0,65); 1,2491 (0,63); 1,1929 (3,24); 1,1751 (6,4); 1,1572 (3,15); 0,0079 (0,43); -0,0002 (11,12); -0,0085 (0,43)

23-78 4-chlor-phenyl CH(CF3) CH2 H

Tabelle 24

Verbindungen der Formel 1-24

1-24

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

Verbindung Nr. 24-1 , Solvent: [DMSO], Spektrometer: 399.95MHz

8,6018 (1 ,23); 8,5881 (2,29); 8,5742 (1 ,19); 8,3155 (0,44); 7,802 (5,99); 7,789 (6,33); 7,4795 (2,37); 7,363 (1 ,02); 7,3567 (8,04); 7,3518 (3,4); 7,3466 (7,6); 7,3407 (8,93); 7,3354 (16); 7,2709

24-1 4-chlor-phenyl CH2 CH2 H (1 ,7); 7,265 (10,87); 7,2603 (3,25); 7,2485

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

(2,58); 7,244 (6,87); 7,202 (2,52); 4,0379 (0,79); 4,0201 (0,82); 3,4588 (2,1 ); 3,4416 (4,42); 3,4268 (4,35); 3,4087 (2,3); 3,322 (68,28); 2,8414 (4,01 ); 2,8233 (7,02); 2,8055 (3,57); 2,6754 (0,49); 2,6708 (0,67); 2,6663 (0,49); 2,5241 (2,39); 2,5107 (38,3); 2,5063 (75,73); 2,5017 (98,94); 2,4972 (71 ,15); 2,4927 (34,13); 2,3328 (0,48); 2,3285 (0,66); 2,3239 (0,47); 1 ,9887 (3,59); 1 ,2494 (0,36); 1 ,1927 (0,97); 1 , 1749 (1 ,9); 1 ,1571 (0,94); 0,0079 (1 ,73); - 0,0002 (46,38); -0,0085 (1 ,59)

Verbindung Nr. 24-2, Solvent: [DMSO],

Spektrometer: 399.95MHz

8,6278 (1 ,72); 8,614 (3,26); 8,6001 (1 ,7); 7,8031

(6,94); 7,7901 (7,4); 7,5858 (6,65); 7,5818

(7,02); 7,4757 (2,83); 7,3787 (1 ,43); 7,3743

(1 ,1 1 ); 7,358 (9,35); 7,3502 (16); 7,3352

(1 1 ,46); 7,1982 (3); 6,5736 (1 ,09); 4,056 (0,95);

4,0383 (2,93); 4,0205 (2,96); 4,0027 (1 ); 3,4908

(2.48) ; 3,4738 (6,47); 3,4586 (6,59); 3,4419 (2,74); 3,3238 (55, 1 ); 2,9641 (5,24); 2,9469 (10,17); 2,9296 (4,56); 2,6759 (0,35); 2,6714 (0,49); 2,6669 (0,37); 2,5068 (55,97); 2,5024 (72,04); 2,498 (53,39); 2,3334 (0,35); 2,3293 (0,47); 2,3246 (0,36); 1 ,9891 (12,66); 1 ,336 (1 ,08); 1 ,2494 (1 ,23); 1 ,2357 (0,52); 1 ,1932 (3,39); 1 ,1754 (6,64); 1 ,1576 (3,31 ); 0,007

24-2 2,4-dichlorphenyl CH2 CH2 H (1 .49) ; -0,0002 (29,67); -0,0083 (1 ,14)

Verbindung Nr. 24-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5559 (1 ,46); 8,5421 (2,72); 8,5282 (1 ,43); 8,3164 (0,36); 7,7816 (6,22); 7,7687 (6,55); 7,4071 (2,5); 7,361 (7,75); 7,3564 (3,12); 7,3447

(4,12) 7,3398 (13,66); 7,3338 (2,76); 7,3284 (7,16) 7,3154 (6,56); 7,2825 (12,61 ); 7,2679 (7,05) 7,2613 (7,73); 7,1296 (2,65); 6,5742 (1 ,02) 4,0563 (0,82); 4,0385 (2,48); 4,0207 (2,49) 4,0029 (0,84); 3,4041 (0,39); 3,3888 (0,49) 3,3844 (0,57); 3,371 (2,43); 3,3568 (3,62) 3,3517 (3,53); 3,3445 (3,48); 3,3413 (3,79) 3,3368 (3,64); 3,3242 (30,15); 3,309 (0,73) 3,2946 (0,45); 3,0927 (1 ,33); 3,0748

24-3 4-chlor-phenyl CH(CH3) CH2 H 3,0568 (2,41 ); 3,0387 (1 ,15); 2,6715

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

(0,35); 2,5112 (21,26); 2,5069 (40,11); 2,5024 (51,39); 2,4979 (37,55); 2,4937 (18,75); 2,329 (0,33); 1,9891 (10,58); 1,3365 (0,37); 1,2494 (0,52); 1,2165 (16); 1,199 (15,75); 1,1933 (4,88); 1,1752 (5,71); 1,1574 (2,85); 0,0077 (1,13); -0,0002 (23,1); -0,0083 (0,95)

Verbindung Nr.24-4, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7041 (2,05); 8,6909 (3,89); 8,6777 (2,01); 7,8323 (8,98); 7,8194 (9,47); 7,5715 (10,01); 7,5651 (10,66); 7,5505 (3,72); 7,4119 (7,89); 7,3842 (5,24); 7,3778 (5,14); 7,3672 (10,53); 7,3621 (7,84); 7,3549 (14,23); 7,2732 (3,88); 7,2404 (11,25); 7,2182 (8,36); 4,2266 (6,05); 4,212 (13,59); 4,1974 (6,57); 4,0559 (1,21); 4,0382 (3,71); 4,0203 (3,74); 4,0026 (1,25); 3,6341 (3,37); 3,6199 (9,51); 3,6057 (9,19); 3,5912 (3,13); 3,3231 (95,29); 2,6758 (0,64); 2,6712 (0,88); 2,6665 (0,65); 2,5243 (3,04); 2,511 (50,26); 2,5067 (98,59); 2,5022 (128,65); 2,4976 (93,43); 2,4932 (45,66); 2,3378 (0,32); 2,3333 (0,62); 2,3289 (0,86); 2,3244 (0,64); 1,989(16); 1,3361 (0,39); 1,2495 (0,54); 1,1929 (4,3); 1,1751 (8,52); 1,1573 (4,17); 0,0079 (2,1);

24-4 2,4-dichlorphenyl CH(CH3) CH2 H -0,0002 (54,16); -0,0085 (2,01)

Verbindung Nr.24-5, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4374 (2,62); 8,416 (2,65); 7,7917 (5,93); 7,7788 (6,24); 7,5632 (5,66); 7,5596 (5,45); 7,356 (0,94); 7,3351 (16); 7,3306 (8,14); 7,3206 (8,89); 7,3077 (6,33); 7,1817 (4,77); 7,0429 (2,38); 6,5736 (0,8); 4,3328 (0,51); 4,3112 (1,16); 4,2954 (1 ,47); 4,2803 (1,13); 4,2589 (0,54); 3,323 (43,65); 2,9677 (1,22); 2,954 (1,4); 2,9336 (3,47); 2,92 (3,2); 2,9025 (3,23); 2,8909 (0,69); 2,8803 (3,05); 2,8685 (1,27); 2,8463 (1 ,25); 2,6757 (0,32); 2,6714 (0,44); 2,6667 (0,34); 2,511 (26,45); 2,5068 (51,4); 2,5023 (66,93); 2,4978 (48,86); 2,4935 (24,19); 2,3333 (0,33); 2,3289 (0,44); 2,3246 (0,32); 1,989 (0,37); 1,2496 (0,43); 1,2182(14,12); 1,2015 (13,92); 0,0079 (1,18); -0,0002 (28,35); -0,0085

24-5 4-chlor-phenyl CH2 CH(CH3) H (1,04)

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

Verbindung Nr. 24-6, Solvent: [DMSO], Spektrometer: 399.95MHz

8,3673 (0,39); 8,3518 (0,77); 8,3362 (0,39); 7,7812 (1 ,95); 7,7682 (2,08); 7,4274 (2,01 ); 7,4223 (0,79); 7,41 1 (1 ,09); 7,4056 (4,35); 7,3995 (0,66); 7,372 (0,67); 7,3659 (4,47); 7,3605 (1 , 16); 7,3493 (0,84); 7,3441 (2,2); 7,317 (2,17); 7,3093 (0,93); 7,3042 (2,1 ); 7,1706 (1 ,64); 7,0318 (0,8); 6,5735 (0,4); 4,0558 (0,42); 4,038 (1 ,26); 4,0202 (1 ,28); 4,0024 (0,43); 3,4097 (2,7); 3,3939 (2,69); 3,3224 (17,03); 2,524 (0,59); 2,5107 (9,78); 2,5063 (19,27); 2,5018 (25,15); 2,4972 (18,14); 2,4928 (8,75); 1 ,9888 (5,57); 1 ,285 (16); 1 , 1928 (1 ,52); 1 ,175 (2,97); 1 ,1572 (1 ,55); 0,0079 (0,46); -0,0002

24-6 4-c lor-phenyl C(CH3)2 CH2 H (1 1 ,85); -0,0085 (0,4)

Verbindung Nr. 24-7, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6818 (2,47); 8,6684 (4,54); 8,6551 (2,47); 7,8185 (12,63); 7,8055 (13,48); 7,5222 (5,31 ); 7,3835 (1 1 ,22); 7,3606 (14,19); 7,3533 (9,67); 7,3499 (12,63); 7,3478 (14,63); 7,3406 (9,98); 7,3376 (9,68); 7,2448 (5,58); 6,9705 (7,5); 6,962 (10,13); 6,9578 (7,23); 6,9493 (9,69); 6,9132 (8,67); 6,91 1 1 (8,98); 6,9049 (6,64); 6,9028 (6,39); 3,4816 (4,69); 3,4639 (10,68); 3,4495 (10,85); 3,4317 (5,5); 3,323 (63,7); 3,0708 (8,93); 3,053 (16); 3,0351 (7,52); 2,6751 (0,55); 2,6707 (0,75); 2,6662 (0,55); 2,524 (2,42); 2,5106 (44,14); 2,5062 (87,93); 2,5016 (1 15,1 ); 2,4971 (82,78); 2,4926 (39,78); 2,3329 (0,56); 2,3284 (0,78); 2,3239 (0,56); 1 ,9886 (0,37); 1 ,336 (0,78); 1 ,2495 (0,91 ); 0,0079 (1 ,91 ); -

24-7 2,4-dichlorphenyl C(CH3)2 CH2 H 0,0002 (52,82); -0,0085 (1 ,77)

Verbindung Nr. 24-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5603 (1 ,57); 8,5466 (2,85); 8,5332 (1 ,49); 7,81 17 (7,45); 7,7988 (7,82); 7,5533 (3,12); 7,4145 (6,59); 7,383 (0,33); 7,3533 (8,98); 7,3443 (10,3); 7,3402 (1 1 ,18); 7,3284 (4,49); 7,3234 (16); 7,3174 (2,28); 7,2755 (3,63); 7,2625 (13,91 ); 7,2414 (8,3); 4,038 (0,69);

24-8 3,4-dichlorphenyl CH2 CH2 H 4,0202 (0,69); 3,3222 (73,2); 3,2429 (2,71 );

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

(0,42); 2,3295 (0,57); 2,3251 (0,42); 1,9894 (16); 1,3366 (0,65); 1,2497 (0,78); 1,1932 (4,36); 1,1754 (8,58); 1,1576 (4,22); 0,0079 ( ,68); -0,0002 (42,76); -0,0085 ( ,37)

Verbindung Nr.24-11, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6095 (2,34); 8,5955 (4,48); 8,582 (2,35); 8,3162 (0,49); 7,8169(11,27); 7,8039 (11,94); 7,5563 (4,65); 7,4997 (11,61); 7,4932 (12,31); 7,4605 (11,84); 7,4391 (15,84); 7,4175 (10,11); 7,3586 (12,53); 7,3456 (11,93); 7,3355 (0,47); 7,322 (8,17); 7,3154 (7,79); 7,3006 (6,11); 7,2941 (5,8); 7,2787 (4,99); 6,5741 (1,68); 4,0563 (1 ,21 ); 4,0385 (3,67); 4,0207 (3,69); 4,0029 (1,25); 3,3231 (73,71); 3,2869 (3,83); 3,2699 (9,1); 3,255 (9,1); 3,238 (3,93); 2,7451 (7,06); 2,7264 (9,23); 2,7065 (7,58); 2,6807 (0,4); 2,6763 (0,71); 2,6716 (0,94); 2,6671 (0,69); 2,5419 (0,61); 2,5249 (2,86); 2,5115 (51,05); 2,5071 (101,32); 2,5026 (132,53); 2,498 (95,7); 2,4936 (46,22); 2,3338 (0,63); 2,3293 (0,84); 2,3249 (0,62); 1,9893 (16); 1,8444 (2,01); 1,8263 (5,62); 1,8075 (7,18); 1,7888 (5,26); 1,7709 (1,74); 1,3363 (0,79); 1,2495 (0,93); 1,1932 (4,29); 1,1878 (0,55); 1,1754 (8,44); 1,1576 (4,18); 0,0079 (2,2); -0,0002

24-11 2,4-dichlorphenyl CH2 CH2 CH2 H (60,79); -0,0085 (2,02)

Verbindung Nr.24-12, Solvent: [DMSO], Spektrometer: 399.95MHz

8,7049 (1,93); 8,6916 (3,77); 8,6782 (1,93); 8,3163 (0,55); 7,8328 (9,47); 7,8198 (10,06); 7,5718 (11,35); 7,5653 (12,08); 7,5587 (0,62); 7,551 (3,77); 7,4124 (8,13); 7,3844 (5,74); 7,378 (5,44); 7,3677 (10,83); 7,3623 (8,3); 7,3554 (15,58); 7,2738(4); 7,2407 (11,98); 7,2184 (8,89); 4,2271 (6,07); 4,2124 (13,83); 4,1979 (6,63); 4,0561 (1,18); 4,0383 (3,64); 4,0205 (3,67); 4,0028 (1,23); 3,6346 (3,3); 3,6204 (9,39); 3,6062 (9,09); 3,5918 (3,08); 3,3238 (75,44); 2,676 (0,47); 2,6715 (0,66); 2,6669 (0,48); 2,5248 (2,05); 2,5199 (3,2); 2,5114 (38,35); 2,507 (76,68); 2,5024 (100,32); 2,4978

24-12 2,4-dichlorphenyl O CH2 CH2 H (71,87); 2,4933 (34,39); 2,3337 (0,49); 2,3292

Physikalische Daten: ¹ H-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

(0,67); 2,3246 (0,49); 1 ,9893 (16); 1 ,3363 (0,46); 1 ,2495 (0,59); 1 ,193 (4,26); 1 ,1752 (8,46); 1 ,1574 (4,16); 0,0079 (1 ,73); -0,0002 (48,37); -0,0085 (1 ,56)

Tabelle 25

Verbindungen der Formel 1-25

1-25

Physikalische Daten: ¹ H-NMR, 6 |ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

Verbindung Nr. 25-1 , Solvent: [DMSO], Spektrometer: 399.95MHz

7,9396 (1 ,73); 7,931 1 (1 ,73); 7,7686 (4,15);

25-1 4-chlor-phenyl CH2 CH2 H 7,7583 (4,54); 7,7548 (4,19); 7,7446 (3,91 );

Physikalische Daten: Ή-N R, 6 [ppm]

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

7,365 (1,08); 7,3586 (9,94); 7,3537 (3,55); 7,3426 (4,21); 7,3375 (16); 7,3314 (2,15); 7,2699 (2,33); 7,2639 (13,49); 7,2589 (3,78); 7,2476 (3,25); 7,2428 (8,57); 7,2365 (0,98); 7,0835 (9,5); 7,0697 (9,18); 6,5721 (0,36); 5,7547 (1,61); 3,5072 (0,68); 3,476 (2,67); 3,4593 (5,26); 3,4407 (5,18); 3,425 (2,98); 3,41 (0,77); 3,3553 (461,2); 3,2932 (0,55); 2,8362 (5,17); 2,8174 (7,81); 2,7996 (4,57); 2,6778 (0,41); 2,6732 (0,57); 2,6687 (0,41); 2,5263 (1,92); 2,5216 (2,98); 2,5132 (32,03); 2,5087 (63,88); 2,5041 (83,46); 2,4995 (59,25); 2,4949 (27,68); 2,4805 (0,37); 2,3353 (0,41); 2,3308 (0,55); 2,3262(0,38); 1,3357 (0,55); 1,2491 (0,75); 1,2344 (0,65); 0,0079 (2,41); -0,0002 (65,23); -0,0086(1,89)

Verbindung Nr.25-2, Solvent: [DMSO], Spektrometer: 399.95MHz

8,0023 (2,51); 7,9943 (2,51); 7,7674 (5,03); 7,7572 (5,61); 7,7536 (5,21); 7,7434 (4,71); 7,5816 (8,7); 7,5771 (9,04); 7,3837 (2,16); 7,379 (1,59); 7,3631 (11,86); 7,3583 (13,1); 7,3537 (16); 7,3331 (2,5); 7,0815 (11,78); 7,0677 (11,39); 5,7565 (4,11); 3,5066 (3,17); 3,4897 (7,56); 3,4738 (7,79); 3,4568 (3,54); 3,3451 (371,93); 3,3111 (0,64); 3,298 (0,43); 2,9592 (7); 2,9415 (12,52); 2,9239 (6,12); 2,6778 (0,37); 2,6734 (0,5); 2,6689 (0,36); 2,5265 (1,86); 2,5132 (30,07); 2,5088 (58,71); 2,5043 (75,77); 2,4997 (53,82); 2,4952 (25,54); 2,3356 (0,35); 2,3311 (0,47); 2,3263 (0,33); 0,0079

25-2 2,4-dichlorphenyl CH2 CH2 H (2,13); -0,0002 (51,9); -0,0085 (1,6)

Verbindung Nr.25-3, Solvent: [DMSO], Spektrometer: 399.95MHz

7,9346 (2,57); 7,9275 (2,56); 7,7655 (6,73); 7,7552 (7,31); 7,7516 (6,79); 7,7414 (6,4); 7,2983 (5,13); 7,2944 (2,15); 7,2798 (13,24); 7,2661 (4,1); 7,2616 (12,84); 7,2272 (11,38); 7,2234 (16); 7,2182 (3,44); 7,2065 (8,26); 7,1937 (3,37); 7,1902 (4,43); 7,1867 (2,31); 7,177 (2,56); 7,1724 (6,78); 7,1671 (1,63); 7,1581 (1,5); 7,1545 (2,44); 7,1511 (1,21); 7,087

25-3 4-chlor-phenyl CH2 CH2 CH2 H (14,65); 7,0798 (0,7); 7,0732 (14,16); 3,3639

Tabelle 26

Verbindungen der Formel 1-26

1-26

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

26-1 2,4-dichlor-phenyl CH2 CH2 - H Verbindung Nr. 26-1 , Solvent: [DMSO],

Physikalische Daten: ¹ H-NMR, 6 [ppm]

Bsp.-Nr. X L ¹ CAS- bzw. Patent-Nr.

Spektrometer: 399.95MHz

8,6356 (1 ,81 ); 8,6217 (3,48); 8,6076 (1 ,81 ); 8,0013 (8, 12); 7,9979 (8,15); 7,5901 (8,38); 7,5858 (8,97); 7,3883 (2,12); 7,3837 (1 ,45); 7,3676 (13,18); 7,3629 (15,31 ); 7,3594 (16); 7,3463 (0,38); 7,3393 (2,12); 6,9491 (6,58); 6,9467 (8,59); 6,9444 (8,51 ); 6,9422 (6,61 ); 3,4761 (3, 16); 3,459 (7,5); 3,4439 (7,54); 3,4265 (3,54); 3,3616 (0,46); 3,334 (191 ,59); 3,3173 (1 ,15); 2,9412 (6,66); 2,9235 (12,39); 2,906 (5,9); 2,6728 (0,45); 2,5262 (1 ,26); 2,5215 (1 ,88); 2,5128 (25,55); 2,5083 (52,22); 2,5037 (68,89); 2,4991 (49,05); 2,4945 (23,19); 2,335 (0,33); 2,3304 (0,46); 2,3259 (0,32); 1 ,3365 (0,41 ); 1 ,2495 (0,54); 0,008 (0,8); -0,0002 (26,28); -0,0085 (0,81 )

Verbindung Nr. 26-2, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6089 (1 ,36); 8,5953 (2,55); 8,5815 (1 ,37); 8,0014 (6,37); 7,998 (6,33); 7,3655 (1 ,01 ); 7,3591 (9,75); 7,3542 (3,36); 7,3431 (4,14); 7,338 (16); 7,3319 (2,07); 7,2734 (1 ,83); 7,2673 (13,57); 7,2623 (3,77); 7,251 (3,01 ); 7,2462 (8,58); 7,2399 (0,95); 6,9496 (5,06); 6,9473 (6,6); 6,945 (6,59); 6,9428 (5, 15); 3,4476 (2,67); 3,4303 (5,32); 3,4155 (5,19); 3,3971 (2,96); 3,3249 (40,22); 2,8185 (5,02); 2,8002 (8,42); 2,7823 (4,48); 2,6715 (0,41 ); 2,5249 (1 ,1 1 ); 2,5202 (1 ,7); 2,51 15 (22,62); 2,507 (45,83); 2,5024 (60,3); 2,4978 (42,9); 2,4932 (20,22); 2,3291 (0,38); 0,008 (0,66); -0,0002 (20,61 ); -

26-2 4-chlor-phenyl CH2 CH2 H 0,0085 (0,59)

Verbindung Nr. 26-3, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5955 (2,06); 8,5818 (3,95); 8,5681 (2,09); 8,0021 (9,72); 7,9986 (9,6); 7,9976 (9,51 ); 7,5544 (13,94); 7,5442 (0,49); 7,5339 (16); 7,5233 (0,5); 7,5132 (1 1 ,75); 7,5082 (12,1 1 ); 7,2416 (6,86); 7,2365 (6,68); 7,221 (6,06); 7,2159 (5,93); 6,9274 (7,73); 6,925 (10, 18); 6,9228 (10,16); 6,9205 (7,97); 5,7561 (2,1 1 ); 4,0387 (0,58); 4,0209 (0,58); 3,4721 (4,13);

26-3 3,4-dichlor-phenyl CH2 CH2 H 3,4548 (10,04); 3,4401 (10,32); 3,4229 (4,64);

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

(0,5)

Verbindung Nr. 26-6, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5641 (1 ,19); 8,5501 (2,3); 8,5357 (1 ,21 ); 7,9831 (5,35); 7,9793 (5,44); 7,3683 (0,77); 7,362 (7,64); 7,3572 (2,63); 7,3458 (3,37); 7,3408 (13,37); 7,3347 (1 ,79); 7,2877 (1 ,7); 7,2817 (12,3); 7,2766 (3,29); 7,2652 (2,54); 7,2604 (7,3); 7,2542 (0,82); 6,8923 (5,43); 6,8902 (5,39); 3,4008 (0,45); 3,39 (0,81 ); 3,3481 (342,01 ); 3,3232 (4,65); 3,3159 (3,57); 3,301 (0,89); 3,2867 (0,42); 3,2831 (0,5); 3,0364 (1 ,26); 3,0186 (2,51 ); 3,0008 (2,44); 2,983 (1 ,12); 2,6729 (0,43); 2,5261 (1 ,29); 2,5129 (25,33); 2,5084 (50,56); 2,5039 (66,04); 2,4993 (47,15); 2,4948 (22,49); 2,3306 (0,44); 1 ,2123 (16); 1 ,1948 (15,69); 0,0079 (0,74); -0,0002

26-6 4-chlor-phenyl CH(CH3) CH2 H (21 ,13); -0,0086 (0,65)

Verbindung Nr. 26-7, Solvent: [DMSO], Spektrometer: 399.95MHz

8,4268 (2,05); 8,4054 (2,08); 7,9942 (4,7); 7,9907 (4,56); 7,9897 (4,56); 7,5685 (3,62); 7,5658 (6,64); 7,5628 (3,95); 7,3486 (16); 7,3455 (15,17); 6,9279 (3,66); 6,9256 (4,79); 6,9234 (4,82); 6,921 1 (3,82); 5,7584 (2,25); 4,3007 (0,46); 4,28 (1 ,06); 4,2639 (1 ,41 ); 4,2481 (1 ,04); 4,2439 (0,82); 4,2271 (0,49); 3,3247 (22,34); 2,9385 (1 ,19); 2,9239 (1 ,34); 2,9043 (3,28); 2,8897 (3,03); 2,873 (3,14); 2,8521 (2,98); 2,8389 (1 ,19); 2,8179 (1 ,23); 2,5252 (0,91 ); 2,5204 (1 ,42); 2,51 19 (17,27); 2,5074 (34,88); 2,5028 (45,79); 2,4982 (32,5); 2,4936 (15,27); 1 , 1769 (13,12); 1 , 1602 (12,99); 0,008

26-7 2,4-dichlor-phenyl CH2 CH(CH3) H (0,5); -0,0002 (15,44); -0,0085 (0,44)

Verbindung Nr. 26-8, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5954 (1 ,56); 8,5809 (2,79); 8,5681 (1 ,33); 7,9821 (6,77); 7,9786 (6,71 ); 7,5619 (9,71 ); 7,5566 (10,19); 7,4648 (5,23); 7,4437 (12); 7,4164 (7,47); 7,41 1 (6,72); 7,3953 (3, 13); 7,3899 (3,06); 6,903 (5,49); 6,9006 (7,06);

26-8 2,4-dichlor-phenyl CH(CH3) CH2 H 6,8984 (6,94); 6,8961 (5,32); 5,7569 (0,7);

Physikalische Daten: ¹ H-NMR, 6 |ppm]

Bsp.-Nr. X L ¹ L- CAS- bzw. Patent-Nr.

(1,68); 7,1645 (1,55); 7,161 (2,54); 7,1576 (1,31); 7,0007 (7,99); 6,9983 (10,42); 6,9961 (10,34); 6,9938 (8); 3,3236 (48,99); 3,2409 (4,43); 3,2233 (8,88); 3,2088 (8,84); 3,1912 (4,61 ); 2,6755 (0,59); 2,6709 (0,79); 2,6663 (0,58); 2,6306 (7,35); 2,6119 (10,08); 2,5921 (8,06); 2,5412 (0,37); 2,5244 (2,29); 2,5197 (3,47); 2,511 (42,44); 2,5065 (86); 2,5019 (112,99); 2,4973 (79,68); 2,4927 (36,96); 2,3333 (0,52); 2,3287 (0,74); 2,3241 (0,52); 1,8216 (2,43); 1,8026(6); 1,7843 (8,01); 1,7661 (5,51); 1,7476 (2,14); 1,3361 (0,52); 1,2493 (0,69); 0,0079 (1,24); -0,0002 (38,22); -0,0086 (1,09)

Verbindung Nr.26-11, Solvent: [DMSO], Spektrometer: 399.95MHz

8,6033 (1 ,98); 8,5896 (3,67); 8,5759 (1 ,96); 8,0134 (9,34); 8,0098 (9,31); 7,5714 (10,58); 7,5663 (10,83); 7,4191 (5,24); 7,3984 (16); 7,3837 (11,47); 7,3786 (10,33); 7,3631 (3,36); 7,3579 (3,54); 7,3482 (0,4); 7,327 (0,57); 7,2584 (0,5); 7,2376 (0,41); 6,997 (7,66); 6,9948 (9,64); 6,9926 (9,29); 6,9905 (6,99); 3,3697 (0,48); 3,3575 (0,88); 3,3347 (213,35); 3,3149 (0,73); 3,2704 (3,55); 3,2532 (8,1); 3,2382 (8,13); 3,2211 (3,66); 2,7359 (6,63); 2,7171 (7,91); 2,6972 (6,97); 2,6779 (0,46); 2,6733 (0,58); 2,6687 (0,42); 2,5266 (1,71); 2,5218 (2,64); 2,5133 (31,11); 2,5088 (62,1); 2,5043 (80,8); 2,4996 (56,99); 2,4951 (26,48); 2,3354 (0,36); 2,331 (0,51 ); 2,3264 (0,36); 1 ,8044 (1 ,96); 1 ,786

(4,98) 1 ,7673 (6,47); 1 ,7488 (4,67); 1 ,7306 (1.64), 1,3368 (0,41); 1,2495 (0,52); 0,008

26-11 2,4-dichlor-phenyl CH2 CH2 CH2 H (0,87); -0,0002 (27,33); -0,0085 (0,8)

Verbindung Nr.26-12, Solvent: [DMSO], Spektrometer: 399.95MHz

8,5982 (2,65); 8,5846 (4,8); 8,5711 (2,62); 8,0104 (12,76); 8,0069 (12,58); 7,3503 (1,8); 7,3334 (3,92); 7,3292 (3,29); 7,3164 (2,73) 7,3125 (7,46); 7,3085 (2,99); 7,2952 (3,48) 7,2916 (4,87); 7,2748 (2,28); 7,1031 (1,07) 7,0986 (1,37); 7,0862 (9,78); 7,0784 (1,87) 7,0659 (16); 7,054 (1,96); 7,0457 (8,06); 7,0326

26-12 2,6-difluor-phenyl CH2 CH2 CH2 H (1,09); 7,0292 (0,81); 6,9798 (10,33); 6,9775

Physikalische Daten: Ή-NMR, 6 [ppm] oder

Bsp.-Nr. X L ¹ L ² L ³ Y CAS- bzw. Patent-Nr.

(13,21); 6,9752 (12,93); 6,9729 (9,92); 6,514 (0,37); 3,328 (26,54); 3,2621 (4,91); 3,2446 (9,9); 3,2293 (9,86); 3,2118 (5,04); 2,6849 (6,61); 2,6657 (10,52); 2,6462 (7,04); 2,527 (1,7); 2,5222 (2,59); 2,5137 (30,04); 2,5092 (59,96); 2,5046 (78,2); 2,5 (55,19); 2,4954 (25,66); 2,336 (0,36); 2,3314 (0,5); 2,3266 (0,35); 1,7839 (2,64); 1,7649 (6,6); 1,7464 (9,32); 1,7277(6,07); 1,7091 (2,29); 1,3377 (0,59); 1,2503 (0,76); 0,008 (0,96); -0,0002 (28,5); -0,0086 (0,8)

Biologische Experimente

Beispiel A

Nippostrongylus brasiliensis-T est (NIPOBR)

Testverfahren für in vitro Experimente mit Nippostrongylus brasiliensis Adulte Nippostrongylus brasiliensis wurden aus dem Dünndarm weiblicher Wistar-Ratten isoliert, in 0.9% NaCl transferiert, das 20 μg/ml Sisomycin und 2 μg/ml Canesten enthielt. Die Inkubation der Würmer (beide Geschlechter) wurde in 1.0 ml Medium durchgeführt, das auch für die Bestimmung der Acetylcholinesterase- Aktivität verwendet wurde. Die Verbindungen wurden in DMSO gelöst und dem Inkubationsmedium zugefügt, sodass Endkonzentrationen von 100, 10 bzw. 1 μg/ml vorhanden waren. Die Kontrollen enthielten nur DMSO. Die Inkubation und die Enzymbestimmung wurden in der Arbeit von Rapson et al. (1987) Z. Parasitenkunde 73, 190-191 beschrieben.

Die Einteilung der Wirksamkeit erfolgte in den Kategorien 35 (0-35% Hemmung), 60 (>35-60%>), 84 (>60-84%) und 100 (>84-100%).

Beispiel-Nummer Wirksamkeit bei 10 μg/ml

1-2 100%

1-7 100%

1-14 100%

1-20 100%

1-22 100%

2-3 100%

2-7 100%

2-8 100%

2-9 100%

2-11 100%

2-12 100%

2-16 100%

2-19 100%

2-20 100%

2-23 100%

3-4 100%

3-9 100%

3-11 100%

3-14 100%

3-15 100% Beispiel-Nummer Wirksamkeit bei 10 μg/ml

3-19 100%

3-20 100%

3-21 100%

4-3 100%

4-5 100%

6-7 100%

13-4 100%

14-4 100%

20-22 100%

Beispiel B

In-vivo Nematodentest

Heligmosomoides polvgyrus I Maus Experimentell mit Heligmosomoides polygyrus infizierte Mäuse wurden nach Ablauf der Präpatenzzeit des Parasiten behandelt. Die Wirkstoffe wurden in einem Cremophor EL/Wassergemisch oral appliziert.

Der Wirkungsgrad wird dadurch bestimmt, dass bei der Sektion der Mäuse die Würmer im Darm ausgezählt werden. Die Wirksamkeit wird über die Wurmzahl in Relation zur Anzahl der Würmer im Darm unbehandelter Kontrolltiere bestimmt. Geprüfte Wirkstoffe und wirksame Dosierungen (Dosis effectiva) sind aus der nachfolgenden Tabelle ersichtlich.

Substanz Wirksamkeit bei 100 mg/kg

4-3 100%

13-4 100%

14-2 100%

17-37 100% Beispiel C

In-vivo Nematodentest

Haemonchus contortus I Schaf

Experimentell mit Haemonchus contortus infizierte Schafe wurden nach Ablauf der Präpatenzzeit des Parasiten behandelt. Die Wirkstoffe wurden als reiner Wirkstoff oral und/oder intramuskulär appliziert.

Der Wirkungsgrad wird dadurch bestimmt, dass bei der Sektion der Schafe die Würmer im Labmagen ausgezählt werden. Die Wirksamkeit wird über die Wurmzahl in Relation zur Anzahl der Würmer im Labmagen unbehandelter Kontrolltiere bestimmt.

Geprüfte Wirkstoffe und wirksame Dosierungen (Dosis effectiva) sind aus der nachfolgenden Tabelle ersichtlich.

Beispiel D

Haemonchus contortus-Ί est (HAEMCO)

Lösungsmittel: Dimethylsulfoxid

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit„Ringerlösung" auf die gewünschte Konzentration. Gefäße mit der Wirkstoffzubereitung der gewünschten Konzentration werden mit ca. 40 Haemonchus contortus Larven besetzt.

Nach 5 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Larven abgetötet wurden; 0 %> bedeutet, dass keine Larven abgetötet wurden.

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100%) bei einer Aufwandmenge von 100 ppm: 20-26, 20-29

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90%o bei einer Aufwandmenge von 20 ppm: 13-4

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%) bei einer Aufwandmenge von 20 ppm: 14-2, 14-4 Cooperia curticei-Test (COOPCU)

Lösungsmittel: Dimethylsulfoxid

Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 10 mg Wirkstoff mit 0,5 ml Dimethylsulfoxid und verdünnt das Konzentrat mit„Ringerlösung" auf die gewünschte Konzentration. Gefäße mit der Wirkstoffzubereitung der gewünschten Konzentration werden mit ca. 40 Cooperia curticei Larven besetzt.

Nach 5 Tagen wird die Abtötung in % bestimmt. Dabei bedeutet 100 %>, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden.

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 100% bei einer Aufwandmenge von 100 ppm: 20-26

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80% bei einer Aufwandmenge von 100 ppm: 17-37

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 90%) bei einer Aufwandmenge von 20 ppm: 14-2, 14-4, 13-4

Bei diesem Test zeigen z.B. die folgenden Verbindungen der Herstellungsbeispiele eine Wirkung von 80%o bei einer Aufwandmenge von 20 ppm: 20-29