FUNGI

Description

The present invention relates to pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions comprising at least one compound I.

In many cases, in particular at low application rates, the fungicidal activity of the known fungi- cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.

Surprisingly, this object is achieved by the use of the inventive pyridine compounds of formula I having favorable fungicidal activity against phytopathogenic fungi.

Accordingly, the present invention relates to the com ounds of formula I

wherein

R ¹ is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, Ci-C ₆ - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein

R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents R ^x1 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

wherein the acyclic moieties of R ¹ are unsubstituted or substituted by groups R ^1a which independently of one another are selected from:

R ^1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ - halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^11a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogen- alkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ¹ are unsubstituted or substituted by groups R ^1b which independently of one another are selected from:

R ^1b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy and Ci-C6-alkylthio;

R ² is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, Ci-C ₆ - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein

R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents R ^x1 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

wherein the acyclic moieties of R ² are unsubstituted or substituted by groups R ^2a which independently of one another are selected from:

R ^2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ - halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsub- stituted or substituted by substituents R ^22a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogen- alkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ² are unsubstituted or

substituted by groups R ^2b which independently of one another are selected from: R ^2b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl,

C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy and Ci-C6-alkylthio;

R ³ is in each case independently selected from CH ₃ , CH ₂ F, CHF ₂ and CF ₃ ;

R ⁴ is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogen- alkynyl, Ci-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0),

C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C ₄ - alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, NO2, SH, NH ₂ , NH(CrC ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , d-C ₆ -alkyl, C C ₆ -halogenalkyl, C ₂ - C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci- C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or

wherein the acyclic moieties of R ⁴ are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R ^4a , which independently of one another are selected from:

R ^a halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C(=0)Ci-C ₄ - alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , Ci-C ₆ -alkoxy, Ci-C ₄ -halogenalkoxy, Ci-C ₆ - alkylthio, Ci-C ₆ -halogenalkylthio, S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0) N H(Ci-C ₆ -alkyl), C(=0)N(C C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(CrC ₄ -al- kyl), N(CrC ₄ -alkyl) ₂ , N H(C(=0)C C ₄ -alkyl), N(C(=0)C C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , Ci- C6-alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkoxy, and S(0) _n -Ci-C6-alkyl; and wherein R ^x , R' and R" are as defined above wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R ⁴ are independently unsubstituted or substituted with identical or different groups R ^4b , which independently of one another are selected from:

R ^b halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C(=0)Ci-C ₄ - alkyl), N(C(=0)d-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , C C ₄ -alkyl, C C ₄ -alkoxy, C C ₄ -halogen- alkyl, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, CrC ₄ -halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0) _n -Ci-C6-alkyl, Ci-C ₄ -alkoxy-Ci-C ₄ -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , C1-C4- alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

and wherein R ^x is as defined above;

n is 0, 1 , 2 or

R ³ , R ⁴ together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N , O and S, wherein the heteroatom N may carry one substituent selected from Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl and S0 ₂ Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN , Ci-C ₄ -al- kyl, halogen, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S0 ₂ , and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R ³⁴ independently selected from halogen, OH , CN , N0 ₂ , SH , N H ₂ , CrC ₆ -alkyl, Ci-C ₆ -halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C ₄ - alkoxy-Ci-C ₄ -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R ^34a selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH ₂ groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and

R ⁵ is H;

R ⁶ is H;

A is selected from below group:

wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.; wherein

Y is H;

o is 0, 1 , 2 or 3; and

R ⁷⁸ are independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R*, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)NH(Ci-C ₆ -alkyl), CR'=NOR", Ci-C ₆ -alkyl, Ci-C ₆ -halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-alkynyl, C ₂ -C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C ₂ -C6-alkenyloxy, C ₂ -C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N , O and S; wherein R ^x , R' and R" are as defined above; and wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted by R ^78a which independently of one another are selected from:

R ^78a halogen, OH , CN , Ci-C ₆ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -cycloalkenyl, C ₃ -C ₆ - halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or substituted by R ^78aa selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;

wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R ⁷⁸ are unsubstituted or substituted by R ^78b which independently of one another are selected from:

R ^78b halogen, OH , CN , Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio;

is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H ₂ , N H(Ci- C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H (C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -alkenyl) ₂ , N H(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkynyl) ₂ , N H(C ₃ -C ₆ -cycloalkyl), N (C ₃ -C ₆ -cycloalkyl) ₂ , N(Ci-C ₄ -alkyl)(C ₂ -C ₄ - alkenyl), N(Ci-C ₄ -alkyl)(C ₂ -C ₄ -alkynyl), N(Ci-C ₄ -alkyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ - alkenyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkenyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkynyl)(C ₃ -C ₆ -cyclo- alkyl), N H(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , S(0) _n -Ci-C ₆ -alkyl, S(0) _n - aryl, Ci-C ₆ -cycloalkylthio, S(0) _n -C ₂ -C ₆ -alkenyl, S(0) _n -C ₂ -C ₆ -alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C ₂ -C ₆ -alkenyl, C(=0)C ₂ -C ₆ -alkynyl, C(=0)C ₃ -C ₆ -cycloalkyl, C(=0)N H (C Ce-alkyl), CH(=S), C(=S)C C ₆ -alkyl, C(=S)C ₂ -C ₆ -alkenyl, C(=S)C ₂ -C ₆ -alkynyl, C(=S)C ₃ - Ce-cycloalkyl, C(=S)N H(Ci-C ₆ -alkyl), Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, OR ^Y , C ₃ - C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein

R ^x is as defined above;

R ^Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6- alkynyl, C ₂ -C6-halogenalkynyl, C ₃ -C6-cycloalkyl, and C ₃ -C6-halogencycloalkyl; wherein the acyclic moieties of R ⁹ are unsubstituted or substituted by groups R ^9a which independently of one another are selected from:

R ^9a halogen, OH , CN , d-Ce-alkoxy, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ⁹ are unsubstituted or

substituted by groups R ^9b which independently of one another are selected from:

R ^9b halogen, OH , CN , C C ₄ -alkyl, C C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; R ¹⁰ is in each case independently selected from the substituents as defined for R ⁹ , wherein the possible substituents for R ¹⁰ are R ^10a and R ^10b , respectively, which correspond to R ^9a and R ^9b , respectively;

R ⁹ , R ¹⁰ together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent R ^N selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S0 ₂ Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R ¹¹ ) _m , wherein m is 0, 1 , 2, 3 or 4;

R ¹¹ is in each case independently selected from halogen, OH, CN, NO2, SH, NH ₂ , NH(Ci-C4- alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , d-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, Ci-C ₆ - alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;

wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH ₂ groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein

R ^x is as defined above;

wherein the acyclic moieties of R ¹¹ are unsubstituted or substituted with identical or different groups R ^11a which independently of one another are selected from:

R ^11a halogen, OH, CN, Ci-C ₆ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^111a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio;

wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R ¹¹ unsubstituted or substituted with identical or different groups R ^11b which independently of one another are selected from:

R ^11b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; with the provisio that f A is phenyl,

R ¹ is H; and

R ⁴ can not be unsubstituted Ci-C6-alkyl; and

R ¹⁰ can not be H

and the N-oxides and the agriculturally acceptable salts thereof.

Compounds of formula I can be accessed e.g. starting from alcohols of type II with nitriles of type III in the presence of an acid in an organic solvent (see for example US 2008/0275242 or WO2005/070917). Preferably, sulfuric acid or a sulfonic acid, in particular triflic acid, are used as acid. Most suitable solvents are hydrocarbons, preferably benzene or dichloromethane. In the following schemes, the optionally substituted phenyl or heteroaryl formed by W together with the partially substituted pyridine ring to which it is attached is sketched by a semicircle named "A":

Depending on the nature of the starting materials, the reaction is performed at a temperature from -40°C to 200°C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room or ambient temperature (about 23°C) to 80°C.

Nitriles of type II I are either commercially available or can be prepared by a skilled person from the corresponding halides following literature precedures (see, for example Journal of Organic Chemistry, 76(2), 665-668; 201 1 ; Angewandte Chemie, International Edition, 52(38), 10035- 10039; 2013; WO2004/013094).

Alcohols of type I I can be prepared as described below. A skilled person will realize that compounds of type l llb can be reacted with organometallic reagents, preferably alkyl Grignard or al- kyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type I I.

lllb

Alternatively, alcohols of type I I can be prepared from epoxydes I l ia and compounds VI (see below):

"metallation"

The metallation reaction may preferably be carried out using Lithium-organic compounds, such as for example n-butyl lithium, sec-butyl lithium or tert-butyl lithium to result in an exchange of halogen by lithium. Also suitable is the reaction with magnesium resulting in the formation of the respective Grignard reagents. A further possibility is the use of other Grignard reagents such as isopropyl-magnesium-bromide instead of Mg.

A typical preparation of compounds of type l llb can be achieved by reacting compounds of type IV with organometallic reagents, preferably alkyl Grignard or alkyl-Lithium reagents, in ethereal solvents, preferably THF at low temperatures and under inert conditions to furnish compounds of type III as previously reported (see for example WO2012051036; WO201 1042918).

Compounds of type IV can be accessed by reacting a carbonyl compound of type V, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with NH(OR')R", wherein R' and R" are selected from (Ci-C4)-alkyl, most preferably being methyl, in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0 °C and ambient temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. US 20130324506; Tetrahedron: Asymmetry, 17(4), 508-51 1 ; 2006). If X = OH, the addition of an activating reagent, preferably a carbodiimide, may be preferred (see for example ChemMedChem, 7(12), 2101 -21 12; 2012; 201 1038204; Journal of Organic Chemistry, 76( 1 ), 164-169; 201 1 ).

If required, compounds of type V can be prepared from the corresponding aryl halides of type VI (Hal is halogen, preferably Br or I). As described (Tetrahedron, 68(9), 21 13-2120; 2012; Chemical Communications (Cambridge, United Kingdom), 49(60). 6767-6769; 2013), aryl halides will react with compounds of type VII in the presence of a transition metal catalyst, preferably a cop- per(l) salt, in an organic solvent, preferably DMF or DMSO, at elevated temperatures. Typically a base, preferably potassium phosphate, is added.

If appropriate, compounds of type II can be prepared as follows. A known or commercially available compound of type VIII can be reacted with an organometallic reagent of type IX, preferably a Grignard or an organolithium reagent, readily prepared by a skilled person. Preferably, the reaction is performed in a temperature range from -78 °C to room temperature under inert conditions in an ethereal solvent.

Alternatively compounds I in which R ⁵ stands for hydrogen can be accessed by reacting a ni- trile III with an olefin ll ^# under acidic conditions as described elsewhere (US 7632783, B2, page 60, method A).

I

Alternatively compounds I can be prepared via intramolecular reaction of amide X when A is an electron-rich carbon- or heterocycle. The intramolecular cyclization will take place in the presence of a dehydrating agent in an organic solvent (WO 2008143263, Synthetic Communications 2007, 37, 1331 -1338.). Preferably, phosphoryl chloride (POCI ₃ ), POCI3/P2O5, H3PO4/P2O5, SnCU or BF3 are used as dehydrating agent. Most suitable solvents are hydrocarbons, prefera- bly benzene, toluene or acetonitrile. Alternatively halogenated solvents can be used, for example dichloromethane, chloroform or chlorobenzene.

Depending on the nature of starting materials, the reaction is performed at temperature from - 40°c to 200 °C, in particular from -10°C to 120°C, more specifically from 0°C to 100°C, even more specifically from room temperature to 100°C.

Amides of type X can accessed by reacting a carbonyl of type XI, preferably a carboxylic acid (X = OH) or an acid chloride (X = CI), with an amines of type XII in an organic solvent, preferably THF or dichloromethane. Typically the reaction is performed in a range between 0°C and room temperature in the presence of an organic base, preferably N(C2Hs)3 or pyridine (see e.g. WO 8303968). If X = OH, the addition of an activating agent, preferably a carbodiimide or acid chloride, may be preferred (see e.g Bioorganic & Medicinal Chemistry, 2010, 18, 3088-31 15).

If required, compounds of type XII can be synthesized from the correspond nitriles. As de- scribed Synlett. 2007, 4 652-654 or Tetrahedron 2012, 68, 2696-2703, nitriles will react with or- ganometallic agents, preferably Grignard or Lithium reagent, in ethereal solvents, preferably THF at low temperature and under inert conditions to furnish compounds of type XII. The synthesis of compounds of type XII can take place in two steps or one pot.

The N-oxides may be prepared from the inventive compounds according to conventional oxidation methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ). The oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the ta- bles below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.

The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X: The intermediate compounds of formula X are novel. Consequently, one aspect of the present invention relates to compounds of formula X:

The compounds of formula X have fungicidal activity and the details below referring to the pounds I also apply to compounds X.

Particular embodiments of the compounds X are the following compounds

Xk

If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be controlled.

In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "C _n -C _m " indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.

The term "halogen" refers to fluorine, chlorine, bromine and iodine.

The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1-methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1-methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri- methylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methylpropyl. Likewise, the term "C2-C4-alkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1-dimethylethyl (tert.-butyl).

The term "CrC ₆ -halogenalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C2-halogenalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-

2.2- difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.

The term "Ci-C6-hydroxyalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.

The term "CrC4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C6-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C6-alkoxy group (as defined above).

The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. Examples are "C2-C4-alkenyl" groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.

The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-al- kynyl" groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-

3- ynyl, 1 -methyl-prop-2-ynyl.

The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are "C1-C4- alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1-dimethylethoxy.

The term "Ci-C6-halogenalkoxy" refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C4-halogenalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,

2.3- difluoro-"propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -fluo- romethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2-bromoethoxy,

4- fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.

The term "C2-C6-alkenyloxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are "C2-C4-alkenyloxy" groups.

The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are "C2-C4-alkynyloxy" groups.

The term "C3-C6-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".

The term "C3-C6-cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".

The term "C3-C8-cycloalkyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).

The term "Ci-Ce-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term "Ci- C6-halogenalkylthio" as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.

The term "C(=0)-Ci-C6-alkyl" refers to a radical which is attached through the carbon atom of the group C(=0) as indicated by the number valence of the carbon atom. The number of valence of carbon is 4, that of nitrogen is 3. Likewise the following terms are to be construed: NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C ₃ -C ₆ -cycloalkyl), N(C ₃ -C ₆ -cycloalkyl) ₂ , C(=0)-NH(Ci-C ₆ - alkyl), C(=0)-N(Ci-C ₆ -alkyl) ₂ .

The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S" is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:

a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and

a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,

1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5- yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxa- zolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5- yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4- yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyra- zol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropy- razol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydro- pyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihy- dropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidi- nyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tet- rahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hex- ahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4- hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and

a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4,5-tetrahydro[1 H]azepin-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5- ,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxa- zepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.

The term "substituted" refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.

The term "5-or 6-membered heteroaryl" or "5-or 6-membered heteroaromatic" refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,

a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or

a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. The inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.

Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.

In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detained, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.

Furthermore, in respect of the variables, generally, the embodiments of the compounds I also apply to the intermediates.

R ¹ according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;

wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein

R ^x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;

wherein the acyclic moieties of R ¹ are unsubstituted or substituted with identical or different groups R ^1a which independently of one another are selected from:

R ^1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ¹ are unsubstituted or substituted with identical or different groups R ^1b which independently of one another are selected from:

R ^1b halogen, OH, CN, C C ₄ -alkyl, C C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio. For every R ¹ that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R ¹ that may be present in the ring.

According to one embodiment of formula I, R ¹ is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.

According to another embodiment of formula I, R ¹ is hydrogen.

According to still another embodiment of formula I, R ¹ is halogen, in particular Br, F or CI, more specifically F or CI.

According to another embodiment of formula I, R ¹ is F

According to another embodiment of formula I, R ¹ is CI

According to another embodiment of formula I, R ¹ is Br.

According to still another embodiment of formula I, R ¹ is OH.

According to still another embodiment of formula I, R ¹ is CN.

According to still another embodiment of formula I, R ¹ is NO2.

According to still another embodiment of formula I, R ¹ is SH.

According to still another embodiment of formula I R ¹ is NH ₂ , NH(CrC4-alkyl), N(CrC4-alkyl) ₂ or NH-S02-R ^X , wherein R ^x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy.

According to still another embodiment of formula I, R ¹ is Ci-C6-alkyl, in particular Ci-C4-alkyl,

According to still another embodiment of formula I, R ¹ is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF ₃ , CHF ₂ , CH ₂ F, CCI ₃ , CHCI ₂ , CH ₂ CI, CF ₃ CH ₂ , CCI ₃ CH ₂ or CF ₂ CHF ₂ .

According to still another embodiment of formula I, R ¹ is C ₂ -C6-alkenyl or C ₂ -C6-halogenalkenyl, in particular C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -halogenalkenyl, such as CH=CH ₂ , C(CH ₃ )=CH ₂ , CH=CCI ₂ , CH=CF ₂ , CCI=CCI ₂ , CF=CF ₂ , CH=CH ₂ , CH ₂ CH=CCI ₂ , CH ₂ CH=CF ₂ , CH ₂ CCI=CCI ₂ , CH ₂ CF=CF ₂ , CCI ₂ CH=CCI ₂ , CF ₂ CH=CF ₂ , CCI ₂ CCI=CCI ₂ , or CF ₂ CF=CF ₂ .

According to still another embodiment of formula I, R ¹ is C ₂ -C6-alkynyl or C ₂ -C6-halogenalkynyl, in particular C ₂ -C ₄ -alkynyl or C ₂ -C ₄ -halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH ₂ C≡CH, CH ₂ C≡CCI, or CH ₂ C≡CF.

According to still another embodiment of formula I, R ¹ is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C ₂ -alkoxy such as OCH ₃ or OCH ₂ CH ₃ .

According to still another embodiment of formula I, R ¹ is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C ₂ -halogenalkoxy such as OCF ₃ , OCHF ₂ , OCH ₂ F, OCCI ₃ , OCHCI ₂ or OCH ₂ CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to still another embodiment of formula I R ¹ is C3-C6-cycloalkyl, in particular cyclopro- pyl. According to still another embodiment of formula I, R ¹ is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R ^1b as defined and preferably herein.

According to still another embodiment of formula I, R ¹ is C3-C6-halogencycloalkyl. In a special embodiment R ¹ is fully or partially halogenated cyclopropyl.

According to still another embodiment of formula I, R ¹ is unsubstituted aryl or aryl that is substituted by one, two, three or four R ^1b , as defined herein. In particular, R ¹ is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R ^1b , as defined herein.

According to still another embodiment of formula I, R ¹ is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R ¹ is 5- or 6-membered heteroaryl that is substituted by one, two or three R ^1b , as defined herein.

According to still another embodiment of formula l,R ¹ is in each case independently selected from hydrogen, halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C6-alkyl, C ₂ -C6-alkenyl, C ₂ -C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R ¹ are not further substituted or carry one, two, three, four or five identical or different groups R ^1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R ¹ are not further substituted or carry one, two, three, four or five identical or different groups R ^1b as defined below.

According to still another embodiment of formula I, R ¹ is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and CrC ₄ -halogenalkoxy.

R ^1a are the possible substituents for the acyclic moieties of R ¹ .

R ^1a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^11a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci- C ₄ -halogenalkoxy, in particular selected from halogen, Ci-C ₂ -alkyl, Ci-C ₂ -halogenalkyl, Ci-C ₂ - alkoxy and Ci-C ₂ -halogenalkoxy, more specifically selected from halogen, such as F, CI and Br. In to one embodiment R ^1a is independently selected from halogen, OH, CN, Ci-C ₂ -alkoxy, C ₃ - C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C ₂ -halogenalkoxy. Specifically, R ^1a is

independently selected from F, CI, OH, CN, Ci-C ₂ -alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl and Ci-C ₂ -halogenalkoxy.

According to one embodiment R ^1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.

According to still another embodiment of formula I, R ^1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C ₂ -halogenalkoxy. Specifically, R ^1a is

independently selected from OH, cyclopropyl and Ci-C ₂ -halogenalkoxy.

R ^1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R ¹ .

R ^1b according to the invention is independently selected from halogen, OH, CN, Ci-C ₄ -alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.

According to one embodiment thereof R ^1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R ^1b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F ₂ -cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy.

According to still another embodiment thereof R ^1b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R ^1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F ₂ -cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF ₂ , OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F ₂ -cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF ₂ and OCF ₃ .

R ^x in the substituent NH-S02-R ^X is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted by one, two, three, four or five substituents R ^x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy. In particular, R ^x is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted by one, two or three R ^x1 independently selected from Ci-C2-alkyl, more specifically R ^x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted by one CH3., more specifically S02-R ^x is the tosyl group ("Ts").

Particularly preferred embodiments of R ¹ according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1-16 corresponds to one particular embodiment of the inven- tion. Thereby, for every R ¹ that is present in the inventive compounds, these specific

embodiments and preferences apply independently of the meaning of any other R ¹ that may be present in the ring:

Table P1 :

"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.

30 R ² according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, NO2, SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;

wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein

R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x2 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

wherein the acyclic moieties of R ² are unsubstituted or substituted with identical or different groups R ^2a which independently of one another are selected from:

R ^2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C ₄ -halogen- alkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^22a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ - halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ² are unsubstituted or substituted with identical or different groups R ^2b which independently of one another are selected from:

R ^2b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halogencycloalky, Ci-C ₄ -halogenalkoxy and Ci-C6-alkylthio.

For every R ² that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of the other R ² that may be present in the ring.

According to one embodiment of formula I, R ² is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH ₃ , F or CI most preferred H, F or CI.

According to another of formula I, R ² is halogen, in particular Br, F or CI, more specifically F or CI.

According to another embodiment of formula I, R ² is F

According to another embodiment of formula I, R ² is CI

According to another embodiment of formula I, R ² is Br.

According to still another embodiment of formula I, R ² is hydrogen

According to still another embodiment of formula I, R ² is OH.

According to still another embodiment of formula I, R ² is CN.

According to still another embodiment of formula I, R ² is N0 ₂ .

According to still another embodiment of formula I, R ² is SH.

In a further specific embodiment R ² is NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ or NH-S0 ₂ -R ^x , wherein R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x2 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy, or Ci-C ₄ -halogenalkoxy. According to still another embodiment of formula I, R ² is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH ₃ or CH ₂ CH ₃ .

According to still another embodiment of formula I, R ² is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF ₃ , CHF ₂ , CH ₂ F, CCI ₃ , CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF ₂ CHF ₂ . According to still a further embodiment, R ² is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C ₂ -C ₄ -alkenyl or C ₂ -C ₄ -halogenalkenyl, such as CH=CH ₂ , CH=CCI ₂ , CH=CF ₂ , CCI=CCI ₂ , CF=CF ₂ , CH=CH ₂ , CH ₂ CH=CCI ₂ , CH ₂ CH=CF ₂ , CH ₂ CCI=CCI ₂ , CH ₂ CF=CF ₂ , CCI ₂ CH=CCI ₂ , CF ₂ CH=CF ₂ , CCI ₂ CCI=CCI ₂ , or CF ₂ CF=CF ₂ .

According to still a further embodiment, R ² is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C ₂ -C ₄ -alkynyl or C ₂ -C ₄ -halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH ₂ C≡CH, CH ₂ C≡CCI, or CH ₂ C≡CF.

According to still another embodiment of formula I, R ² is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.

According to still another embodiment of formula I, R ² is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF ₃ , OCHF ₂ , OCH ₂ F, OCCI3, OCHC or OCH2CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

In a further specific embodiment R ² is C3-C6-cycloalkyl, in particular cyclopropyl.

In a further specific embodiment, R ² is C3-C6-cycloalkyl, for example cyclopropyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R ^2b as de- fined and preferably herein.

According to still another embodiment of formula I, R ² is C3-C6-halogencycloalkyl. In a special embodiment R ² is fully or partially halogenated cyclopropyl.

According to still another embodiment of formula I, R ² is unsubstituted aryl or aryl that is substituted by one, two, three or four R ^2b , as defined herein. In particular, R ² is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R ^2b , as defined herein.

According to still another embodiment of formula I, R ² is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R ² is 5- or 6-membered heteroaryl that is substituted by one, two or three R ^2b , as defined herein.

According to still another embodiment of formula I, R ² is in each case independently selected from hydrogen, halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R ² are not further substituted or carry one, two, three, four or five identical or different groups R ^2a as defined below and wherein the cycloalkyl moieties of R ² are not further substituted or carry one, two, three, four or five identical or different groups R ^2b as defined below. According to still another embodiment of formula I, R ² is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.

R ^2a are the possible substituents for the acyclic moieties of R ² . R ^2a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.

According to one embodiment R ^2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R ^2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.

According to one embodiment R ^2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.

According to still another embodiment of formula I, R ^2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R ^2a is

independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.

R ^2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R ² .

R ^2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.

According to one embodiment thereof R ^2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R ^2b is independently selected from F, CI, OH, CN, CH ₃ , OCH ₃ , cyclopropyl, 1-F-cyclopropyl, 1-CI-cyclopropyl and halogenmethoxy.

According to still another embodiment thereof R ^2b is independently selected from halogen, C-i- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R ^2b is independently selected from halogen, OH, CH3, OCH3, CN, CHF2, OCHF2, OCF3, OCH3 cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1-F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1-CI ₂ -cyclopropyl, OCHF ₂ and OCF ₃ .

Particularly preferred embodiments of R ² according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the invention. Thereby, for every R ² that is present in the inventive compounds, these specific

embodiments and preferences apply independently of the meaning of any other R ² that may be present in the ring:

Table P2:

"Ts" in the table stands for the tosylgroup S02-(p-CH ₃ )phenyl.

R ³ is in each case independently selected from CH3, CH2F, CHF2 and CF3.

According to one embodiment R ³ is CH3.

According to another embodiment R ³ is CH ₂ F.

According to still another embodiment R ³ is CHF ₂ .

According to another embodiment R ³ is CF3.

R ⁴ is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci- C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are inde- pendently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(CrC ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , d-C ₆ -alkyl, C C ₆ -halo- genalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; or wherein the acyclic moieties of R ⁴ are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R ^4a , which independently of one another are selected from:

R ^a halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , C C ₆ -alkoxy, C C ₄ -halogenalkoxy, C C ₆ -alkylthio, C C ₆ -halo- genalkylthio, S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)C C ₆ -alkyl, C(=0)0(C C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocy- cle contains independently one, two, three or four heteroatoms selected from N, O and S;

wherein the carbo-, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ - alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein R ^x , R' and R" are as defined above;

wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R ⁴ are independently unsubstituted or substituted with identical or different groups R ^4b , which independently of one another are selected from:

R ^4b halogen, OH, CN, N0 ₂ , SH, NH _2, NH(C C ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH(C(=0)C C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , d-C ₄ -alkyl, Ci-C ₄ -alkoxy, C C ₄ -halogenalkyl, C ₃ -C ₆ -cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0) _n -Ci-C6-a lkyl, Ci-C ₄ -alkoxy-Ci-C ₄ -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy; and wherein R ^x is as defined above;

n is 0, 1 , 2.

R ⁴ is independently selected from CN, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C6-alkyl, Ci- C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-alkynyl, C ₂ -C6-halogenalkynyl, Ci- C6-alkoxy, C ₂ -C6-alkenyloxy, C ₂ -C6-alkynyloxy, Ci-C6-halogenalkoxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, CrC ₄ -alkyl, C ₂ -C6-alkenyl, C ₂ -C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are inde- pendently unsubstituted or substituted by R'" which is independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, Ci-C ₆ -halo- genalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-alkynyl, C ₂ -C6-halogenalkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl and phenyl; or wherein the acyclic moieties of R ⁴ are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R ^4a , which independently of one another are selected from: R ^a halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , Ci-C ₆ -alkoxy, Ci-C ₄ -halogenalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ -halo- genalkylthio, S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)N H(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N , O and S;

wherein the carbo-, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen,

OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ - alkyl) ₂ , N H-S0 ₂ -R ^x , Ci-C ₆ -alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein R ^x , R' and R" are as defined above;

wherein the carbo-, heterocyclic, heteroaryl and aryl moieties of R ⁴ are independently unsubsti- tuted or substituted with identical or different groups R ^4b , which independently of one another are selected from:

R ^b halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0) _n -Ci-C6-a lkyl, Ci-C ₄ -alkoxy-Ci-C ₄ -alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy; and wherein R ^x is as defined above;

n is 0, 1 , 2.

According to one embodiment of formula I, R ⁴ is selected from R ⁴ is in each case independently selected from CN , Ci-C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C3-C6-cycloalkenyl, C ₂ -C ₆ -alkynyl, C ₂ -C ₆ -halogenalkynyl, C ₃ -C ₆ -cycloalkynyl, CH(=0), C(=0)Ci-C ₆ -alkyl,

C(=0)0(Ci-C ₆ -alkyl), CR'=NOR", C ₃ -C ₆ -halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl or aryl; and Ci-C6-alkyl substituted by CN , C C ₆ -alkoxy, d-C ₄ -halogenalkoxy, C C ₆ -alkylthio, S(0) _n -CrC ₆ -alkyl, N H- S0 ₂ -R ^x , N(CrC ₆ -alkyl) ₂ , CH(=0), C(=0)C C ₆ -alkyl, C(=0)0(C C ₆ -alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein R ^x , R' and R" are defined below; and wherein the acyclic moieties of R ⁴ are unsubstituted or substituted with identical or different groups R ^4a as defined below and wherein wherein the carbo-, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R ^4b as defined below.

According to one embodiment of formula I, R ⁴ is selected from R ⁴ is in each case independently selected from C ₂ -C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C3-C6-cycloalkenyl, C ₂ - Ce-alkynyl, C ₂ -C ₆ -halogenalkynyl, C ₃ -C ₆ -cycloalkynyl, CH(=0), C(=0)C ₂ -C ₆ -alkyl, C(=0)0(C ₂ - C6-alkyl), CR'=NOR" , C3-C6-halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl or aryl; and Ci-C6-alkyl substituted by CN , d-Ce-alkoxy, Ci-C ₄ -halogenalkoxy, Ci-C ₆ -alkylthio, S(0) _n -Ci-C ₆ -alkyl, N H-S0 ₂ -R ^x , N(Ci-C ₆ - alkyl) ₂ , CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein R ^x , R' and R" are defined below; and wherein the acyclic moieties of R ⁴ are unsubstituted or substituted with identical or different groups R ^4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R ^4b as defined below.

According to still another embodiment of formula I, R ⁴ is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R ⁴ is selected from Ci-C6-halogenalkyl, phenyl-Ch , halogenphenyl-Chb, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted by substituents R ^4b as defined below.

According to still another embodiment of formula I, R ⁴ is selected from Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R ^4b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R ⁴ is selected from substituted Ci-C6-hal- ogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted bysubstituents R ^4b as de- fined below.

According to another embodiment of formula I, R ⁴ is selected from C2-C6-alkenyl, C2-C6-halo- genalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted by halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R ⁴ are unsubstituted or substituted with identical or different groups R ^4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R ^4b as defined below.

According to still another embodiment of formula I, R ⁴ is selected from CN, C2-C6-alkenyl, C2-C6- halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R ⁴ are unsubstituted or substituted with identical or different groups R ^4a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted by substituents R ^4b as defined below.

According to still another embodiment of formula I, R ⁴ is CN.

According to still another embodiment of formula I, R ⁴ is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or

According to still another embodiment of formula I, R ⁴ is Ci-C6-halogenalkylthio, such as SCF ₃ , According to still another embodiment of formula I, R ⁴ is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to still another embodiment of formula I, R ⁴ is Ci-C6-alkyl such as CH3. According to still another embodiment of formula I, R ⁴ is Ci-C6-alkyl such as C2H5. According to still another embodiment of formula I, R ⁴ is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted by at least one group R ^4a , which independently of one another are selected from:

R ^4a halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , C C ₆ -alkoxy, C C ₄ -halogenalkoxy, Ci-C ₆ -alkylthio, C C ₆ - halogenalkylthio, S(0) _n -CrC ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)C C ₆ -alkyl, C(=0)0(C C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), C(=0)N(Ci-C ₆ -alkyl) ₂ , CR'=NOR" a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of hal- ogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH(C(=0)C C ₄ -alkyl),

N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ - alkoxy, Ci-C ₄ -halogenalkoxy, and S(0)n-Ci-C6-alkyl.

According to still another embodiment of formula I, R ⁴ is CH3 is substituted by at least one group R ^4a , which independently of one another are selected from:

R ^4a halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkoxy, Ci-C ₄ -halogenalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ - halogenalkylthio, S(0) _n -CrC ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)C C ₆ -alkyl, C(=0)0(C C ₆ -alkyl), C(=0)NH(CrC ₆ -alkyl), C(=0)N(C C ₆ -alkyl) ₂ , CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of hal- ogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH(C(=0)d-C ₄ -alkyl),

N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , C C ₆ -alkylthio, Ci-C ₄ -alkyl, C C ₄ -halogenalkyl, Ci-C ₄ - alkoxy, Ci-C ₄ -halogenalkoxy, and S(0)n-Ci-C6-alkyl.

According to still another embodiment of formula I, R ⁴ is C ₂ Hs is substituted by at least one group R ^4a , which independently of one another are selected from:

R ^4a halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkoxy, Ci-C ₄ -halogenalkoxy, Ci-C ₆ -alkylthio, Ci-C ₆ - halogenalkylthio, S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(CrC ₆ -alkyl), C(=0)N(C C ₆ -alkyl) _2, CR'=NOR"a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, an aryl or phenoxy, wherein in each case one or two CH ₂ groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl),

N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, C1-C4- alkoxy, Ci-C ₄ -halogenalkoxy, and S(0)n-Ci-C6-alkyl.

According to still another embodiment of formula I, R ⁴ is CH ₂ CN.

According to still another embodiment of formula I, R ⁴ is CH ₂ OH.

According to still another embodiment of formula I, R ⁴ is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C ₂ -halogenalkyl, such as CF3, CCI3, FCH ₂ , CICH ₂ , F ₂ CH, CI ₂ CH, CF ₃ CH ₂ , CCI ₃ CH ₂ or CF ₂ CHF ₂ .

According to still a further embodiment of formula I, R ⁴ is C ₂ -C6-alkenyl, in particular C ₂ -C ₄ -alk- enyl, such as CH=CH ₂ , CH ₂ CH=CH ₂ or C(CH ₃ )C=CH ₂ .

According to a further specific embodiment of formula I, R ⁴ is C ₂ -C6-halogenalkenyl, in particular C ₂ -C ₄ -halogenalkenyl, more specifically C ₂ -C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF ₂ , CH=CCI ₂ , CF=CF ₂ , CCI=CCI ₂ , CH ₂ CH=CHF, CH ₂ CH=CHCI, CH ₂ CH=CF ₂ ,

CH ₂ CH=CCI ₂ , CH ₂ CF=CF ₂ , CH ₂ CCI=CCI ₂ , CF ₂ CF=CF ₂ or CCI ₂ CCI=CCI ₂ .

According to still a further embodiment of formula I, R ⁴ is C ₂ -C6-cycloalkenyl, in particular C ₂ -C ₄ - cycloalkenyl, such as CH=CH ₂ -cPr.

According to still a further embodiment of formula I, R ⁴ is C ₂ -C6-alkynyl or C ₂ -C6-halogenalkynyl, in particular C ₂ -C ₄ -alkynyl or C ₂ -C ₄ -halogenalkynyl, such as C CH, C C-CI, CH ₂ - C≡CH, CH ₂ -C≡CCI or CH ₂ - C≡C-CH ₃ .

According to still a further embodiment of formula I, R ⁴ is C ₂ -C6-cycloalkynyl in particular C ₂ -C ₄ - cycloalkynyl, such as C C-cPr.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C ₂ -alkoxy such as OCH3, CH ₂ CH3 or CH ₂ OCH3.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C ₄ -alkyl-Ci-C ₄ -alkoxy, more specifically Ci-C ₂ -alkyl-Ci-C ₂ -alkoxy, such as

According to a further specific embodiment of formula I, R ⁴ is C ₂ -C6-alkenyloxy, in particular C ₂ - C ₄ -alkenyloxy, more specifically Ci-C ₂ -alkenyloxy such as OCH=CH ₂ , OCH ₂ CH=CH ₂

OC(CH ₃ )CH=CH ₂ , CH ₂ OCH=CH ₂ , or CH ₂ OCH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I, R ⁴ is C ₂ -C6-alkynyloxy, in particular C ₂ - C ₄ -alkynyloxy, more specifically Ci-C ₂ -alkynyloxy such as OC CH, OCH ₂ C=CH or CH ₂ OC=CH

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-halogenalkoxy, in particular Ci-C ₄ -halogenalkoxy, more specifically Ci-C ₂ -halogenalkoxy such as OCF3, OCHF ₂ , OCH ₂ F, OCCI3, OCHCI ₂ or OCH ₂ CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C ₄ -alkyl-Ci-C ₄ -halogenalkoxy, more specifically Ci-C ₂ -alkyl-Ci-C ₂ -halogenalkoxy such as CH ₂ OCF ₃ , CH ₂ OCHF ₂ , CH ₂ OCH ₂ F, CH ₂ OCCI ₃ , CH ₂ OCHCI ₂ or CH ₂ OCH ₂ CI, in particular CH ₂ OCF ₃ , CH ₂ OCHF ₂ , CH ₂ OCCI ₃ or CH ₂ OCHCI ₂ . According to a further specific embodiment of formula I, R ⁴ is CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl) or C(=0)N(Ci-C ₆ -alkyl) ₂ , wherein alkyl is CH ₃ , C ₂ H ₅ , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ⁴ is Ci-C4-alkyl-CH(=0), Ci-C ₄ -alkyl- C(=0)Ci-C ₆ -alkyl, Ci-C ₄ -alkyl-C(=0)0(Ci-C ₆ -alkyl), Ci-C ₄ -alkyl-C(=0)NH(Ci-C ₆ -alkyl) or Ci-C ₄ - alkyl-C(=0)N(Ci-C ₆ -alkyl) ₂ , especially CH ₂ CH(=0), CH ₂ C(=0)CrC ₆ -alkyl, CH ₂ C(=0)0(C C ₆ - alkyl), CH ₂ C(=0)NH(C C ₆ -alkyl) or CH ₂ C(=0)N(CrC ₆ -alkyl) ₂ wherein alkyl is CH ₃ , C ₂ H ₅ , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ⁴ is CR'=NOR" such as

C(CH ₃ )=NOCH ₃ , C(CH ₃ )=NOCH ₂ CH ₃ or C(CH ₃ )=NOCF ₃ .

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-NH(Ci-C ₄ -alkyl) or Ci- C6-alkyl-N(Ci-C ₄ -alkyl) ₂ , wherein alkyl is CH ₃ , C ₂ H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-S(0) _n -CrC ₆ -alkyl, wherein alkyl is CH ₃ , C ₂ H ₅ , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-S(0) _n -Ci-C6- halogenalkyl, wherein halogenalkyl is CF ₃ or CHF ₂ and n is 1 , 2 or 3.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-S(0) _n -aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R ^4b which independently of one another are selected from halogen, Ci-C ₂ -alkyl, Ci-C ₂ -alkoxy, Ci-C ₂ -halogenalkyl, Ci-C ₂ -halogenalkoxy and S(0) _n -Ci-C6-alkyl, in particular F, CI, Br, CH ₃ , OCH ₃ , CF ₃ , CHF ₂ , OCHF ₂ , OCF ₃ . According to one embodiment, R ⁴ is unsubstituted phenyl. According to another embodiment, R ⁴ is phenyl, that is substituted by one, two or three, in par- ticular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.

According to a further specific embodiment of formula I, R ⁴ is Ci-C6-alkyl-NH-S0 ₂ -R ^x wherein R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x2 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, CrC ₄ -halogenalkyl, Ci-C ₄ -alkoxy, or CrC ₄ -halogenalkoxy, such as CH ₂ NHS0 ₂ CF ₃ or

CH ₂ NHS0 ₂ CH ₃ .

According to still another embodiment of formula I, R ⁴ is selected from Ci-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or sub- stituted by substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.

According to one embodiment, R ⁴ is selected from Ci-C6-alkyl, especially CH ₂ which is substituted by a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b . According to one embodiment, R ⁴ is selected from Ci-C6-alkyl, especially Chb which is substituted by a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to one embodiment, R ⁴ is selected from Ci-C6-alkyl, especially with R optionally substituted CH ₂ which is substituted by a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to one embodiment, R ⁴ is selected from Ci-C6-alkyl, especially Chb which is substi- tuted by a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to a further specific embodiment of formula I , R ⁴ is Ci-C6-alkyl, especially Chb substituted by a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in par- ticular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to a further specific embodiment of formula I , R ⁴ is Ci-C6-alkyl, especially Chb substituted by a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to a further specific embodiment of formula I , R ⁴ is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b . According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I , it is substituted by R ^4b .

According to a further specific embodiment of formula I , R ⁴ is Ci-C6-alkyl, especially Chb substituted by a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups Ch are replaced by C(=0).

According to still another embodiment of formula I , R ⁴ is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted by substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. According to still another embodiment of formula I, R ⁴ is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.

According to still a further embodiment, R ⁴ is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.

According to still another embodiment of formula I, R ⁴ is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-mem- bered, wherein the carbocycle is unsubstituted or substituted by substituents R ^4b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.

According to one embodiment, R ⁴ is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ⁴ is a 3-membered saturated carbocycle, which is

unsubstituted such as cyclopropyl

According to one embodiment, R ⁴ is a 3-membered saturated carbocycle, which is substituted by halogen, more specifically by F, such as C3H3F2.

According to one embodiment, R ⁴ is a 3-membered saturated carbocycle, which is substituted by halogen. More specifically by CI, such as C3H3CI2.

According to one embodiment, R ⁴ is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ⁴ is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ⁴ is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to still another embodiment of formula I, R ⁴ is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R ^4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, R ⁴ is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R ^4b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodiments of R ⁴ described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.

According to one embodiment, R ⁴ is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to still another embodiment of formula I, R ⁴ is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ⁴ .

According to still another embodiment of formula I, R ⁴ is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b . According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to still another embodiment of formula I, R ⁴ is phenyl-Ci-C6-alkyl, such as phenyl- CH ₂ , wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R ^4b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) _n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH ₃ , OCH ₃ , CF ₃ , CHF ₂ , OCHF ₂ , OCF ₃ and S(0) ₂ CH ₃ .

According to still another embodiment of formula I, R ⁴ is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R ^4b which independently of one another are selected from from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) _n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH ₃ , OCH ₃ , CF ₃ , CHF ₂ , OCHF ₂ , OCF ₃ . According to one embodiment, R ⁴ is unsubstituted phenyl. According to another embodiment, R ⁴ is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI. According to still another embodiment of formula I, R ⁴ is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.

According to still another embodiment of formula I, R ⁴ is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

Particularly preferred embodiments of R ⁴ according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-129 corresponds to one particular embodiment of the invention, wherein P4-1 to P4-129 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R ⁴ is bound is marked with "#" in the drawings.

According to still another embodiment of formula I, R ³ , R ⁴ together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from CN, Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R ³⁴ independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , d-Ce-alkyl, Ci-C ₆ -halogenalkyl, Ci-C ₆ -alkoxy, Ci- C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R ^34a selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halo- genalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH ₂ groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S).

According to one embodiment, R ³ and R ⁴ form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b . According to one embodiment, R ³ and R ⁴ form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ^4b .

According to one embodiment, R ³ and R ⁴ form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^4b . According to still another embodiment of formula I, it is substituted by R ⁴ .

Particularly preferred embodiments of combinations of R ³ and R ⁴ according to the invention are in Table P34 below, wherein each line of lines P34-1 to P34-535 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-535 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R ³ and R ⁴ are bound is marked with ^* in the drawings. "Ts" in the drawings stands for the tosylgroup SO2- (p-CH3)phenyl.

Table P34

No. R3 R ⁴ No. R3 R ⁴

P34-1 CHs CFs P34-3 CHs CH2CI

P34-2 CHs CH ₂ F P34-4 CHs CHF ₂

No. R ³ R ⁴ No. R ³ R ⁴

P34-136 CH ₂ F CH ₂ CCI ₃ P34-162 CH ₂ F #

P34-137 CH ₂ F CF ₂ CHF ₂

P34-138 CH ₂ F CH ₂ OCH ₃ P34-163 CH ₂ F

P34-139 CH ₂ F CH ₂ OCH ₂ F CI ^ff

P34-140 CH ₂ F CH ₂ OCHF ₂ P34-164 CH ₂ F

P34-141 CH ₂ F CH ₂ OCF ₃

P34-142 CH ₂ F CH ₂ OCF ₂ CHF ₂ P34-165 CH ₂ F

P34-143 CH ₂ F CH ₂ NHMe

P34-144 CH ₂ F CH ₂ SMe P34-166 CH ₂ F

P34-145 CH ₂ F CH ₂ SOMe

P34-146 CH ₂ F CH ₂ S0 ₂ Me P34-167 CH ₂ F

P34-147 CH ₂ F CH ₂ NMe ₂

P34-148 CH ₂ F CH ₂ NS0 ₂ CF ₃ P34-168 CH ₂ F

P34-149 CH ₂ F CH ₂ NS0 ₂ CH ₃

P34-150 CH ₂ F CN

P34-169 CH ₂ F 0

P34-151 CH ₂ F CH ₂ CN

P34-152 CH ₂ F CHO

P34-153 CH ₂ F COMe P34-170 CH ₂ F 0

P34-154 CH ₂ F C0 ₂ Me

P34-155 CH ₂ F CH ₂ CHO 0

P34-156 CH ₂ F CH ₂ COMe P34-171 CH ₂ F

P34-157 CH ₂ F CH ₂ C0 ₂ Me

# O—

P34-158 CH ₂ F

P34-172 CH ₂ F

P34-159 CH ₂ F # o-cF ₃

P34-173 CH ₂ F

P34-160 CH ₂ F

#

P34-161 CH ₂ F

No. R ³ R ⁴ No. R ³ R ⁴

P34-265 CHF ₂ CH ₂ CCI ₃ P34-291 CHF ₂ #

P34-266 CHF ₂ CF ₂ CHF ₂

P34-267 CHF ₂ CH ₂ OCH ₃ P34-292 CHF ₂

P34-268 F CI ^ff

CHF ₂ CH ₂ OCH ₂

P34-269 CHF ₂ CH ₂ OCHF ₂ P34-293 CHF ₂

P34-270 CHF ₂ CH ₂ OCF ₃

P34-271 CHF ₂ CH ₂ OCF ₂ CHF ₂ P34-294 CHF ₂

P34-272 CHF ₂ CH ₂ NHMe

P34-273 CHF ₂ CH ₂ SMe P34-295 CHF ₂

P34-274 CHF ₂ CH ₂ SOMe

P34-275 CHF ₂ CH ₂ S0 ₂ Me P34-296 CHF ₂

P34-276 CHF ₂ CH ₂ NMe ₂

P34-277 CHF ₂ CH ₂ NS0 ₂ CF ₃ P34-297 CHF ₂

P34-278 CHF ₂ CH ₂ NS0 ₂ CH ₃

P34-279 CHF ₂ CN

P34-298 CHF ₂ 0

P34-280 CHF ₂ CH ₂ CN

P34-281 CHF ₂ CHO

P34-282 CHF ₂ COMe P34-299 CHF ₂ 0

P34-283 CHF ₂ C0 ₂ Me

P34-284 CHF ₂ CH ₂ CHO 0

P34-285 CHF ₂ CH ₂ COMe P34-300 CHF ₂

P34-286 CHF ₂ CH ₂ C0 ₂ Me

# O—

P34-287 CHF ₂

P34-301 CHF ₂

P34-288 CHF ₂ # o-cF ₃

P34-302 CHF ₂

P34-289 CHF ₂

#

P34-290 CHF ₂

R ^4a are the possible substituents for the the acyclic moieties of R ⁴ and the R ^4a are in each case independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH(C(=0)CrC ₄ -alkyl), N(C(=0)C C ₄ -alkyl) ₂ , NH-S0 ₂ -R*, C C ₆ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0) _n -Ci-C6- alkyl, S(0) _n -aryl, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl), CR'=NOR", heterocarbocycle, aryl and phenoxy, wherein the aryl and phenyl groups are independently unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkylthio, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ - alkoxy, Ci-C ₄ -halogenalkoxy and S(0) _n -Ci-C6-alkyl, wherein in each case one or two CH ₂ groups of the heterocycle may be replaced by a group independently selected from C(=0) or C(=S), and wherein the heterocycle contain independently one, two, three or four heteroatoms selected from N, O or S;

According to one preferred embodiment, R ^4a is in each case independently selected from halogen, OH, CN, NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl) and CR'=NOR". According to one preferred embodiment, R ^4a is in each case independently selected from OH, CN, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)0(Ci-C ₆ -alkyl), C(=0)NH(Ci-C ₆ -alkyl) such as CN, CHO, C(0)0(CH ₃ ) ,C0 ₂ NH(CH ₃ ) or C0 ₂ N(CH ₃ ) ₂ .

According to one preferred embodiment, R ^4a is in each case independently selected from C1-C6- alkylthio, Ci-C ₆ -halogenalkylthio, S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, such as SCH ₃ , S0 ₂ CH ₃ , S0 ₂ Ph.

According to one preferred embodiment, R ^4a is in each case independently selected from NH(CrC ₄ -alkyl), N(C C ₄ -alkyl) ₂ , NH-S0 ₂ -R*, such as NH(CH ₃ ), N(CH ₃ ) ₂ or NHS0 ₂ CH ₃ , NHS0 ₂ CF ₃ .

According to one preferred embodiment, R ^4a is in each case independently selected from C ₃ -C6- cycloalkyl, C ₃ -C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cyclo- propyl.

According to one preferred embodiment, R ^4a is in each case independently selected from C1-C6- alkoxy, Ci-C ₆ -halogenalkoxy, such as OCF ₃ , OCHF ₂ , OCH ₂ F, OCCI ₃ , OCHCI ₂ or OCH ₂ CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to one preferred embodiment, R ^4a is in each case independently selected from heter- ocarbocycle, wherein the heretocyclocycle is a satureated, two CH ₂ groups are replaced by C(=0) and contains one N as a ring member.

According to one preferred embodiment, R ^4a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH ₃ , CHF ₂ , OCH ₃ , OCHFs, CN or S0 ₂ CH ₃ .

According to one preferred embodiment, R ^4a is in each case independently selected from halogen, OH, CN, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl and heterocycle, wherein the heretocyclocycle is a satureated and contains one N as a ring member.

According to one preferred embodiment, R ^4a is in each case independently selected from halo- gen, OH, CN, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl and heterocycle, wherein the heretocyclocycle is a satureated, one CH ₂ group is replaced by C(=0) and contains one N as a ring member.

According to one preferred embodiment, R ^4a is in each case independently selected from halogen, OH, CN, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated, two CH ₂ groups are replaced by C(=0) and contains one N as a ring member.

According to one preferred embodiment, R ^4a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, phenyl and aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH ₃ , CHF ₂ , OCH ₃ , OCHF ₃ , CN or S0 ₂ CH ₃ . According to one further preferred embodiment, R ^4a is in each case independently selected from halogen, phenyl and halogenphenyl, wherein the halogenphenyl is substituted by halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.

According to one further preferred embodiment, R ^4a is in each case independently selected from halogen, CN, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C ₄ -halogenalkoxy, Ci- C6-alkylthio, Ci-C6-halogenalkylthio, phenyl, wherein the phenyl is substituted by halogen selected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy. According to one further preferred embodiment, R ^4a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted by hal- ogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.

R ^4b are the possible substituents for the carbocycle, heterocycle, heteroaryl and aryl moieties and are independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(C C ₄ -alkyl), N(C C ₄ - alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R*, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci- C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0) _n -Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phe- noxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.

According to one preferred embodiment, R ^4b is in each case independently selected from halo- gen, OH, CN, SH, Ci-C ₆ -alkyl, Ci-C ₆ -halogenalkyl, CrC ₆ -alkoxy, CrC ₆ -halogenalkoxy, CrC ₆ - alkylthio and S(0) _n -Ci-C6-alkyl. According to one further preferred embodiment, R ^4b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0) _n -Ci-C6-alkyl. According to one further particular embodiment, R ^4b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one fur- ther particular embodiment, R ^4b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R ^4b is in each case independently selected from Ci-C6-alkoxy, such as OCH ₃ . According to one further particular embodiment, R ^4b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF ₂ and OCF ₃ . According to one further particular embodiment, R ^4b is in each case independently selected from S(0) _n -Ci-C ₆ -alkyl. such as S0 ₂ CH ₃ .

R ⁵ is H.

R ⁶ is H.

A is selected from below group:

wherein, the positions of the rings marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I.

According to one preferred embodiment, A is

According to one preferred embodiment, A is

According to one preferred embodiment, A is

Y is H.

R ⁷⁸ are independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)NH(Ci-C ₆ -alkyl), CR'=NOR", Ci-C ₆ -alkyl, Ci-C ₆ -halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-alkynyl, C ₂ -C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C ₂ -C6-alkenyloxy, C ₂ -C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-mem- bered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroa- toms selected from N, O and S and wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted by R ^78a which independently of one another are selected from:

halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or substituted by R ^78aa selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;

wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R ⁷⁸ are unsubstituted or substituted by R ^78b which independently of one another are selected from:

R ^78b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio.

According to still another embodiment of formula l,o is 0.

According to still another embodiment of formula I , o is 1.

According to still another embodiment of formula I , o is 2 or 3. According to one specific embodiment thereof, o is 2. According to still another embodiment of formula I, o is 3.

For every R ⁷⁸ that is present in the compounds of formula I , the following embodiments and preferences apply independently of the meaning of any other R ⁷⁸ that may be present in the ring. Furthermore, the particular embodiments and preferences given herein for R ⁷⁸ apply inde- pendently for each of o=1 , o=2 and o=3.

According to one embodiment of formula I , R ⁷⁸ is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.

According to one embodiment of formula I , R ⁷⁸ is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.

According to still another embodiment of formula I , R ⁷⁸ is F.

According to still another embodiment of formula I , R ⁷⁸ is CI.

According to still another embodiment of formula I , R ⁷⁸ is Br.

According to still another embodiment of formula I , R ⁷⁸ is OH .

According to still another embodiment of formula I , R ⁷⁸ is CN.

According to still another embodiment of formula I , R ⁷⁸ is NO2.

According to still another embodiment of formula I , R ⁷⁸ is SH.

According to still another embodiment of formula I , R ⁷⁸ is NH2.

According to still another embodiment of formula I , R ⁷⁸ is , NH(Ci-C4-alkyl), in particular

NH(CH ₃ ), NH(C ₂ H ₅ ).

According to still another embodiment of formula I , R ⁷⁸ is , N(Ci-C4-alkyl)2, in particular

NH(CH ₃ ) ₂ , NH(C: According to still another embodiment of formula I, R ⁷⁸ is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH ₃ ), NH(C(=0)(C ₂ H ₅ ).

According to still another embodiment of formula I, R ⁷⁸ is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH ₃ )2, N(C(=0)(C ₂ H ₅ ) ₂ .

According to a further specific embodiment of formula I, R ⁷⁸ is NH-S02-R ^X such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3 or NH-SOz-Ts.

According to a further specific embodiment of formula I, R ⁷⁸ is CH(=0), C(=0)CrC6-alkyl, C(=0)0(Ci-C ₆ -alkyl) or C(=0)NH(Ci-C ₆ -alkyl), wherein alkyl is CH ₃ , C2H5, n-propyl, i-propyl, n- butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ⁷⁸ is CR ^' =NOR ^" such as

C(CH ₃ )=NOCH ₃ , C(CH ₃ )=NOCH ₂ CH ₃ or C(CH ₃ )=NOCF ₃ .

According to still another embodiment of formula I, R ⁷⁸ is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH ₃ . or C2H5, in particular CH ₃ .

According to still another embodiment of formula I, R ⁷⁸ is CH ₂ CH ₃ .

According to still another embodiment of formula I, R ⁷⁸ is CrC6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF ₃ , CCI ₃ , FCH ₂ , CICH2, F ₂ CH, CI2CH, CF ₃ CH ₂ , CCI ₃ CH ₂ or CF ₂ CHF ₂ . According to still a further embodiment of formula I, R ⁷⁸ is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH ₂ or CH ₂ CH=CH ₂

According to a further specific embodiment of formula I, R ⁷⁸ is C2-C6-halogenalkenyl, in particu- lar C2-C4-halogenalkenyl, more specifically C2-C ₃ -halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF ₂ , CH=CCI ₂ , CH ₂ CH=CHF, CH ₂ CH=CHCI, CH ₂ CH=CF ₂ , CH ₂ CH=CCI ₂ . CH ₂ CF=CF ₂ , CH ₂ CCI=CCI ₂ . CF ₂ CF=CF ₂ or CCI ₂ CCI=CCI ₂ .

According to still a further embodiment of formula I, R ⁷⁸ is C ₂ -C6-alkynyl or C ₂ -C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2- C CH, C≡CCI, CH ₂ - C≡CCI, or CCI2- C≡CCI.

According to a further specific embodiment of formula I, R ⁷⁸ is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH ₃ or OCH2CH ₃ .

According to a further specific embodiment of formula I, R ⁷⁸ is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF ₃ , OCHF2, OCH2F, OCCIs, OCHCI2 or OCH2CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to a further specific embodiment of formula I, R ⁷⁸ is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2.

According to a further specific embodiment of formula I, R ⁷⁸ is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH.

According to still another embodiment of formula I R ⁷⁸ is C ₃ -C6-cycloalkyl, in particular cyclopro- pyl.

According to still another embodiment of formula I, R ⁷⁸ is C ₃ -C6-halogencycloalkyl. In a special embodiment R ¹ is fully or partially halogenated cyclopropyl. According to one embodiment, R ⁷⁸ is C3-C6-cycloalkyl, such as a 4-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by

_R 78b

According to one embodiment, R ⁷⁸ is C3-C6-cycloalkyl, such as a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by

_R 78b.

According to one embodiment, R ⁷⁸ is a C3-C6-cycloalkyl, such as 6-membered saturated carbo- cycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by

_R 78b

According to still another embodiment of formula I R ⁷⁸ is C3-C6-cycloalkenyl, in particular cyclo- propenyl.

According to still another embodiment of formula I R ⁷⁸ is S(0)n-Ci-C6-alkyl such as SCH ₃ , S(=0) CH ₃ , S(0) ₂ CH ₃ .

According to still another embodiment of formula I, R ⁷⁸ is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R ^78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, R ⁷⁸ is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted by substituents R ^78b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.

According to still another embodiment of formula I, in the embodiments of R ⁷⁸ described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.

According to one embodiment, R ⁷⁸ is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by R ^78b .

According to still another embodiment of formula I, R ⁷⁸ is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroa- torn. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by _R 78b.

According to still another embodiment of formula I, R ⁷⁸ is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by R ^78b . According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R ^78b . According to still another embodiment of formula I, it is substituted by R ^78b . According to still another embodiment of formula I, R ⁷⁸ is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted by one, two or three identical or different groups R ^78b which independently of one another are selected from halogen, OH, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CHF2, CF ₃ OCHF ₂ , and OCF ₃ .

According to still another embodiment of formula I, R ⁷⁸ is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R78b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, CHF2, OCH3, OCHF2, CF3 and OCF3. According to one embodiment, R ⁷⁸ is unsubstituted phenyl. According to another embodiment, R ⁷⁸ is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.

According to still another embodiment of formula I, R ⁷⁸ is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.

According to still another embodiment of formula I, R ⁷⁸ is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

According to still another embodiment of formula I, R ⁷⁸ is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially un- saturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the carbo- and heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78b as defined and preferably defined herein.

According to still another embodiment of formula I, R ⁷⁸ is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78a as defined and preferably defined herein, and wherein the carbocyclic, heterocyclic, phenyl and heteroaryl moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78b as defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R ⁷⁸ are unsubstituted, according to another embodiment, the acyclic moieties of R ⁷⁸ substituted with identical or different groups R ^78a as defined and preferably defined herein.

According to still another embodiment of formula I , R ⁷⁸ is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3- C6-alkynyloxy and C3-C6-cycloalkyl, wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78b as defined and preferably defined herein.

According to still another embodiment of formula I , R ⁷⁸ is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78a defined and preferably defined herein. According to still another embodiment of formula I , R ⁷⁸ is in each case independently selected from halogen, Ci-C6-alkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R ⁷⁸ are unsubstituted or substituted with identical or different groups R ^78a defined and preferably defined herein. According to one specific embodiment, the acyclic and cyclic moieties of R ⁷⁸ are not further substituted, according to another embodiment, the acyclic moieties of R ⁷⁸ carry one, two, three or four identical or different groups R ^78a as defined and preferably defined herein.

R ^78a are the possible substituents for the acyclic moieties of R ⁷⁸ . R ^78a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogengenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R ^78a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.

According to one preferred embodiment, R ^78a is in each case independently selected from Ci- Ce-alkoxy, Ci-C ₆ -halogenalkoxy, such as OCF ₃ , OCHF ₂ , OCH ₂ F, OCCI ₃ , OCHC or OCH ₂ CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to one preferred embodiment, R ^78a is in each case independently selected from C3- C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cy- clopropyl.

According to still another embodiment of formula I , R ^78a is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyra- zol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxa- zol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4- yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1-yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.

According to still another embodiment of formula I, R ^78a is a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

According to one preferred embodiment, R ^78a is in each case independently selected from aryl, wherein the aryl is substituted by halogen selected from the group consisting of F, CI, Br, CH3, CHF ₂ , OCH3, OCHF3, CN or SO2CH3.

According to one embodiment R ^78a is independently selected from halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R ^78a is independently selected from CN, F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl , 1 ,1 -F ₂ -cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.

According to still another embodiment of formula I, R ^78a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.

R ^78b are the possible substituents for the C3-C6-cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R ⁷⁸ . R ^78b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.

According to one embodiment thereof R ^78b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R ^78b is independently selected from F, CI, CN, CH ₃ , OCH ₃ and halogenmethoxy.

Particularly preferred embodiments of the A ring, optionally substituted by (R ⁷⁸ ) ₀ , according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-40corresponds to one particular embodiment of the invention, wherein P78-1 to P78-40 are also in any combination with one another a preferred embodiment of the present invention. Thereby, the positions of the pheny marked with "#" represents the connection points (carbon atoms 5" and 6" in formula I) with the remaining skeleton of the compounds of formula I:

wherein A is selected from below group

Table P78: No. (R ⁷⁸ )o

No. (R ⁷⁸ )o P78-27 2 ^' -CN

P78-1 o = 0 P78-28 3 ^' -F

P78-2 r-F P78-29 3 -CI

P78-3 r-ci P78-30 3 ^' -Br

P78-4 r-Br P78-31 3 ^' -CH ₃

P78-5 r-CH ₃ P78-32 3 -C ₂ H5

P78-6 1 -C2H5 P78-33 3 ^' -CH ₂ F

P78-7 1 -CH2F P78-34 3 ^' -CHF ₂

P78-8 1 -CHF2 P78-35 3 ^' -CF ₃

P78-9 r-CFs P78-36 3 ^' -OCH ₃

P78-10 1 -OCH3 P78-37 3 ^' -OCH ₂ F

P78-11 1 -OCH2F P78-38 3 ^' -OCHF ₂

P78-12 1 -OCHF2 P78-39 3 ^' -OCF ₃

P78-13 r-ocFs P78-40 3 ^' -CN R ⁹ is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H2, N H(Ci- C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H (C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -alkenyl) ₂ , N H(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -al- kynyl) ₂ , N H(C ₃ -C ₆ -cycloalkyl), N(C ₃ -C ₆ -cycloalkyl) ₂ , N(C2-C ₄ -alkyl)(C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -al- kyl)(C ₂ -C ₄ -alkynyl), N(C2-C ₄ -alkyl)(C ₃ -C ₆ -cycloalkyl), N(C2-C ₄ -alkenyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ - alkenyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkynyl)(C ₃ -C ₆ -cycloalkyl), N H(C(=0)Ci-C ₄ -alkyl),

N(C(=0)CrC ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, CrC ₆ -cycloalkylthio, S(0) _n -C ₂ - Ce-alkenyl, S(0) _n -C ₂ -C ₆ -alkynyl, CH(=0), C(=0)CrC ₆ -alkyl, C(=0)C ₂ -C ₆ -alkenyl, C(=0)C ₂ -C ₆ - alkynyl, C(=0)C ₃ -C ₆ -cycloalkyl, C(=0)N H(Ci-C ₆ -alkyl), CH(=S) , C(=S)Ci-C ₆ -alkyl, C(=S)C ₂ -C ₆ - alkenyl, C(=S)C ₂ -C ₆ -alkynyl, C(=S)C ₃ -C ₆ -cycloalkyl, C(=S)N H(Ci-C ₆ -alkyl), Ci-C ₆ -alkyl, C ₂ -C ₆ - alkenyl, C2-C6-alkynyl, OR ^Y , C ₃ -C6-cycloalkyl, five- or six-membered heteroaryl and aryl;

wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S;

wherein

R ^x is as defined above;

R ^Y is CrC ₆ -alkyl, CrC ₆ -halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl;

wherein the acyclic moieties of R ⁹ are unsubstituted or substituted by groups R ^9a which independently of one another are selected from:

R ^9a halogen, OH , CN , Ci-Ce-alkoxy, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, Ci- C ₄ -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is un- substituted or substituted by substituents R ^{91 a} selected from the group consisting of halogen, OH , Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halo- genalkoxy;

wherein the carbocycle, heteroaryl and aryl moieties of R ⁹ are unsubstituted or

substituted by groups R ^9b which independently of one another are selected from: R ^9b halogen, OH , CN , Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cyclo- alkyl, C ₃ -C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy and Ci-C6-alkylthio;

According to one embodiment of formula I , R ⁹ is selected from the group consisting of H , halogen, CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C ₃ -C6-cycloalkyl, C ₃ -C6-halogency- cloalkyl, and OR ^Y .

According to one embodiment of formula I , R ⁹ is H .

According to still another embodiment of formula I , R ⁹ is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.

According to still another embodiment of formula I , R ⁹ is F.

According to still another embodiment of formula I , R ⁹ is CI.

According to still another embodiment of formula I , R ⁹ is Br.

According to still another embodiment of formula I , R ⁹ is OH .

According to still another embodiment of formula I , R ⁹ is CN .

According to still another embodiment of formula I , R ⁹ is NO2. According to still another embodiment of formula I, R ⁹ is SH.

According to still another embodiment of formula I, R ⁹ is NH2.

According to still another embodiment of formula I, R ⁹ is , NH(Ci-C4-alkyl), in particular NH(CH3), NH(C ₂ H ₅ ).

According to still another embodiment of formula I, R ⁹ is , N(Ci-C4-alkyl)2, in particular NH(CH3)2, NH(C ₂ H ₅ ) ₂ .

According to still another embodiment of formula I, R ⁹ is _, NH(C2-C4-alkenyl), in particular NH(CH=CH ₂ ), NH(CH ₂ CH=CH ₂ ).

According to still another embodiment of formula I, R ⁹ is , N(C2-C4--alkenyl)2, in particular N(CH=CH ₂ ) ₂ , N(CH ₂ CH=CH ₂ ) ₂ .

According to still another embodiment of formula I, R ⁹ is , NH(C2-C4-alkynyl), in particular NH(C= CH), NH(CH ₂ C≡CH).

According to still another embodiment of formula I, R ⁹ is , N(C2-C4-alkynyl)2, in particular N(C= CH) ₂ , N(CH ₂ C≡CH) ₂ .

According to still another embodiment of formula I, R ⁹ is _, NH(C3-C6-cycloalkyl), in particular NH(C ₃ H ₇ ), NH(C ₄ H ₉ ).

According to still another embodiment of formula I, R ⁹ is , N(C3-C6-cycloalkyl)2, in particular N(C ₃ H ₇ ) ₂ , N(C ₄ H ₉ ) ₂ .

According to still another embodiment of formula I, R ⁹ is N(Ci-C4-alkyl)(C2-C4-alkenyl), in particular N(CH ₃ )(CH=CH ₂ ), N(CH3)(CH ₂ CH=CH ₂ ), N(C ₂ H5)(CH=CH ₂ ), N(C ₂ H5)(CH ₂ CH=CH2).

According to still another embodiment of formula I, R ⁹ is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH ₃ )(C≡CH), N(CH ₃ )(CH ₂ C≡CH), N(C ₂ H ₅ )(C≡CH), N(C ₂ H ₅ )(CH ₂ C≡CH).

According to still another embodiment of formula I, R ⁹ is N(CrC4-alkyl)(C ₃ -C6-cycloalkyl), in particular N(CH ₃ )(C ₃ H ₇ ), N(CH3)(C ₄ H ₉ ), N(C ₂ H5)(C ₃ H ₇ ), N(CH ₃ )(C ₄ H ₉ ).

According to still another embodiment of formula I, R ⁹ is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH ₂ )(C≡CH), N(CH ₂ CH=CH2)(CH ₂ C≡CH), N(CH=CH ₂ )(C≡CH),

N(CH ₂ CH=CH ₂ )(CH ₂ C≡CH).

According to still another embodiment of formula I, R ⁹ is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH ₂ )(C ₃ H ₇ ), N(CH ₂ CH=CH2)(C ₄ H ₉ ), N(CH=CH ₂ )(C ₃ H ₇ ), N(CH ₂ CH=CH ₂ )(C ₄ H ₉ ). According to still another embodiment of formula I, R ⁹ is N(C2-C4-alkynyl)(C ₃ -C6-cycloalkyl), in particular N(C≡CH)(C ₃ H ₇ ), N(CH ₂ C≡CH)(C ₄ H ₉ ), N(C≡CH)(C ₃ H ₇ ), N(CH ₂ C≡CH)(C ₄ H ₉ ).

According to still another embodiment of formula I, R ⁹ is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH ₃ ), NH(C(=0)(C ₂ H ₅ ).

According to still another embodiment of formula I, R ⁹ is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH ₃ ) ₂ , N(C(=0)(C ₂ H ₅ ) ₂ .

According to a further specific embodiment of formula I, R ⁹ is NH-S02-R ^X such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3, NH-SO2-TS. According to still another embodiment of formula I , R ⁹ is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH ₃ , S(0) ₂ CH ₃ .

According to still another embodiment of formula I , R ⁹ is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.

According to still another embodiment of formula I , R ⁹ is S(0)n-C2-C6-alkenyl such as

SCH=CH ₂ , S(=0)CH=CH ₂ , S(0) ₂ CH=CH ₂ , SCH ₂ CH=CH ₂ , S(=0)CH ₂ CH=CH ₂ ,

S(0) ₂ CH ₂ CH=CH ₂ .

According to still another embodiment of formula I , R ⁹ is S(0)n-C ₂ -C6-alkynyl such as SC CH, S(=0)C≡CH, S(0) ₂ C≡CH, SCH ₂ C≡CH, S(=0)CH ₂ C≡CH, S(0) ₂ CH ₂ C≡CH.

According to a further specific embodiment of formula I , R ⁹ is CH(=0).

According to a further specific embodiment of formula I , R ⁹ is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C ₂ H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I , R ⁹ is C(=0)C ₂ -C6-alkenyl, C(=0)0(C ₂ - Ce-alkenyl) or C(=0)NH(C ₂ -C ₆ -alkenyl), wherein alkenyl is CH=CH _2, CH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I , R ⁹ is C(=0)C ₂ -C6-alkynyl, C(=0)0(C ₂ - Ce-alkynyl) or C(=0)NH(C ₂ -C ₆ -alkynyl), wherein alkynyl is C≡CH, CH ₂ C≡CH.

According to a further specific embodiment of formula I , R ⁹ is C(=0)C3-C6-cycloalkyl,

C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C ₄ H ₉ ).

According to a further specific embodiment of formula I , R ⁹ is CH(=S).

According to a further specific embodiment of formula I , R ⁹ is C(=S)Ci-C6-alkyl, wherein alkyl is CH3, C ₂ H ₅ , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I , R ⁹ is C(=S)C ₂ -C6-alkenyl, wherein alkenyl is CH=CH ₂ , CH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I , R ⁹ is C(=S)C ₂ -C6-alkynyl, wherein alkynyl is C≡CH, CH ₂ C≡CH.

According to a further specific embodiment of formula I , R ⁹ is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C H9).

According to a further specific embodiment of formula I , R ⁹ is C(=S)NHCrC ₆ -alkyl, wherein alkyl is CH3, C ₂ H ₅ , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to still another embodiment of formula I , R ⁹ is Ci-C6-alkyl, in particular Ci-C ₄ -alkyl, such as CH3. or C ₂ H5, in particular CH3 or CH ₂ CH3.

According to still another embodiment of formula I , R ⁹ is Ci-C6-halogenalkyl, in particular Ci-C ₄ - halogenalkyl, such as CF ₃ , CCI ₃ , FCH ₂ , CICH ₂ , F ₂ CH, CI ₂ CH, CF ₃ CH ₂ , CCI ₃ CH ₂ or CF ₂ CHF ₂ . According to still a further embodiment of formula I , R ⁹ is C ₂ -C6-alkenyl, in particular C ₂ -C ₄ -alk- enyl, such as CH=CH ₂ , C(CH ₃ )=CH ₂ , CH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I , R ⁹ is C ₂ -C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF ₂ , CH=CCI ₂ , CH ₂ CH=CHF, CH ₂ CH=CHCI, CH ₂ CH=CF ₂ , CH ₂ CH=CCI ₂ , CF ₂ CH=CF ₂ , CCI ₂ CH=CCI ₂ , CF ₂ CF=CF ₂ , CCI ₂ CCI=CCI ₂ .

According to still a further embodiment of formula I , R ⁹ is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, Ch C CH, C CCI,

CH ₂ C≡CCI, or CCI ₂ C≡CCI.

According to a further specific embodiment of formula I , R ⁹ is OR ^Y wherein R ^Y is Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl.

According to a further specific embodiment of formula I , R ⁹ is OR ^Y , wherein R ^Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R ⁹ is such as OCH3 or OCH2CH3.

According to a further specific embodiment of formula I , R ⁹ is OR ^Y , wherein R ^Y is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R ⁹ is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ . According to a further specific embodiment of formula I , R ⁹ is OR ^Y wherein R ^Y C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R ⁹ is such as OCH=CH2,

OCH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I , R ⁹ is OR ^Y , wherein R ^Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R ⁹ is such as OC≡CH, OC≡CCI, OCH ₂ C≡CCI, or OCCI ₂ C≡CCI.

According to still another embodiment of formula I R ⁹ is OR ^Y , wherein R ^Y is C3-C6-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I , R ⁹ is OR ^Y wherein R ^Y is C3-C6-halogencyclo- alkyl. In a special embodiment R ¹ is fully or partially halogenated cyclopropyl.

According to still another embodiment of formula I , R ⁹ is is OR ^Y , wherein R ^Y C3-C6-cycloalkenyl, in particular cyclopropenyl.

According to still another embodiment of formula I , R ⁹ is C3-C6-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I , R ⁹ is C3-C6-halogencycloalkyl. In a special embodiment R ^9b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F ₂ -cyclopropyl, 1 , 1 -Cl2-cyclopropyl .

According to still another embodiment of formula I , R ⁹ is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R ^9b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R ⁹ is unsubstituted phenyl. According to another embodiment, R ⁹ is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI. According to still another embodiment of formula I, R ⁹ is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.

According to still another embodiment of formula I, R ⁹ is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

According to still another embodiment of formula I, R ⁹ is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R ⁹ are unsubstituted or substituted with iden- tical or different groups R ^9a as defined and preferably defined herein, and wherein the carbocy- clic, phenyl and heteroaryl moieties of R ⁹ are unsubstituted or substituted with identical or different groups R ^9b as defined and preferably defined herein.

According to still another embodiment of formula I, R ⁹ is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl,, wherein the acyclic moieties of R ⁹ are unsubstituted or substituted with identical or different groups R ^9a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R ⁹ are unsubstituted or substituted with identical or different groups R ^9b as defined and preferably defined herein.

R ^9a are the possible substituents for the acyclic moieties of R ⁹ .

According to one embodiment R ^9a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^91a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.

According to one embodiment R ^9a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R ^9a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 ,1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.

According to still another embodiment of formula I, R ^9a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.

R ^9b are the possible substituents for the cycloalkyi, heteroaryl and phenyl moieties of R ⁹ . R ^9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.

According to one embodiment thereof R ^9b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R ^9b is independently selected from F, CI, CN , CH3, OCH3 and halogenmethoxy.

Particularly preferred embodiments of R ⁹ according to the invention are in Table P13 below, wherein each line of lines P13-1 to P3-43 corresponds to one particular embodiment of the invention, wherein P13-1 to P3-43 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R ⁹ is bound is marked with "#" in the drawings. Table P13:

R ¹⁰ is in each case independently selected from H , halogen, OH , CN , NO2, SH , N H ₂ , N H(Ci- C ₄ -alkyl), N(CrC ₄ -alkyl) ₂ , N H (C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -alkenyl) ₂ , N H(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -al- kynyl) ₂ , N H(C ₃ -C ₆ -cycloalkyl), N(C ₃ -C ₆ -cycloalkyl) ₂ , N(C ₂ -C ₄ -alkyl)(C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -al- kyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkenyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ - alkenyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkynyl)(C ₃ -C ₆ -cycloalkyl), N H(C(=0)Ci-C ₄ -alkyl),

N(C(=0)Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, Ci-Ce-cycloalkylthio, S(0) _n -C ₂ - Ce-alkenyl, S(0) _n -C ₂ -C ₆ -alkynyl, CH(=0), C(=0)Ci-C ₆ -alkyl, C(=0)C ₂ -C ₆ -alkenyl, C(=0)C ₂ -C ₆ - alkynyl, C(=0)C ₃ -C ₆ -cyclpalkyl, C(=0)N H(Ci-C ₆ -alkyl), CH(=S) , C(=S)Ci-C ₆ -alkyl, C(=S)C ₂ -C ₆ - alkenyl, C(=S)C ₂ -C ₆ -alkynyl, C(=S)C ₃ -C ₆ -cyclpalkyl, C(=S)N H(CrC ₆ -alkyl), CrC ₆ -alkyl, C ₂ -C ₆ - alkenyl, C ₂ -C6-alkynyl, OR ^Y , C ₃ -C6-cycloalkyl, five- or six-membered heteroaryl and aryl;

wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S;

wherein

R ^x is as defined above;

R ^Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6- alkynyl, C ₂ -C6-halogenalkynyl, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalkyl;

wherein the acyclic moieties of R ¹⁰ are unsubstituted or substituted by groups R ^10a which independently of one another are selected from:

R ^10a halogen, OH , CN , Ci-C ₆ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halogencycloalkyl, C C ₄ -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^{101 a} selected from the group consisting of halogen, OH , Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halo- genalkoxy;

wherein the carbocyclic, heteroaryl and aryl moieties of R ¹⁰ are unsubstituted or

substituted by groups R ^10b which independently of one another are selected from:

R ^10b halogen, OH , CN , Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, C C ₄ -halogenalkyl, C ₃ -C ₆ -cyclo- alkyl, C ₃ -C6-halogencycloalkyl, CrC ₄ -halogenalkoxy and Ci-C6-alkylthio.

According to one embodiment of formula I, R ¹⁰ is in each case independently selected from halogen, OH , CN , N0 ₂ , SH , N H ₂ , N H(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , N H(C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ - alkenyl) ₂ , N H(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkynyl) ₂ , N H(C ₃ -C ₆ -cycloalkyl), N(C ₃ -C ₆ -cycloalkyl) ₂ , N(C ₂ -C ₄ -alkyl)(C ₂ -C ₄ -alkenyl), N(C ₂ -C ₄ -alkyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkenyl)(C ₂ -C ₄ -alkynyl), N(C ₂ -C ₄ -alkenyl)(C ₃ -C ₆ -cycloalkyl), N(C ₂ -C ₄ -alkynyl)(C ₃ -C ₆ -cy- cloalkyl), N H(C(=0)Ci-C ₄ -alkyl), N(C(=0)Ci-C ₄ -alkyl) ₂ , N H-S0 ₂ -R ^x , S(0) _n -Ci-C ₆ -alkyl, S(0) _n -aryl, Ci-Ce-cycloalkylthio, S(0) _n -C ₂ -C ₆ -alkenyl, S(0) _n -C ₂ -C ₆ -alkynyl, CH(=0), C(=0)C C ₆ -alkyl, C(=0)C ₂ -C ₆ -alkenyl, C(=0)C ₂ -C ₆ -alkynyl, C(=0)C ₃ -C ₆ -cyclpalkyl, C(=0)N H(C C ₆ -alkyl), CH(=S), C(=S)Ci-C ₆ -alkyl, C(=S)C ₂ -C ₆ -alkenyl, C(=S)C ₂ -C ₆ -alkynyl, C(=S)C ₃ -C ₆ -cyclpalkyl, C(=S)NH(Ci-C ₆ -alkyl), Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ -alkynyl, OR ^Y , C ₃ -C ₆ -cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroa- toms selected from N, O and S; wherein

R ^x is as defined above;

R ^Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6- alkynyl, C ₂ -C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl;

wherein the acyclic moieties of R ¹⁰ are unsubstituted or substituted by groups R ^10a which independently of one another are selected from:

R ^10a halogen, OH, CN, Ci-C ₆ -alkoxy, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ -halogencycloalkyl, Ci-

C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^101a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halo- genalkoxy;

wherein the cycloalkyl, heteroaryl and aryl moieties of R ¹⁰ are unsubstituted or

substituted by groups R ^10b which independently of one another are selected from:

R ^10b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cyclo- alkyl, C ₃ -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;

R ¹⁰ is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C ₂ - C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-alkynyl, C ₂ -C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-hal ogenalkoxy and OR ^Y .

According to still another embodiment of formula I, R ¹⁰ is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.

According to still another embodiment of formula I , R ¹⁰ is F.

According to still another embodiment of formula I , R ¹⁰ is CI.

According to still another embodiment of formula I , R ¹⁰ is Br.

According to still another embodiment of formula I , R ¹⁰ is OH.

According to still another embodiment of formula I , R ¹⁰ is CN.

According to still another embodiment of formula I , R ¹⁰ is N0 ₂ .

According to still another embodiment of formula I , R ¹⁰ is SH.

According to still another embodiment of formula I , R ¹⁰ is NH ₂ .

According to still another embodiment of formula I , R ¹⁰ is , NH(C

NH(CH ₃ ), NH(C ₂ H ₅ ).

According to still another embodiment of formula I , R ¹⁰ is , N(Ci-

NH(CH ₃ ) ₂ , NH(C ₂ H ₅ ) ₂ .

According to still another embodiment of formula , NH(C ₂ -C4-alkenyl), in particular NH(CH=CH ₂ ), NH(CH ₂ CH=CH ₂ ).

According to still another embodiment of formula I, R ¹⁰ is , N(C ₂ -C4--alkenyl) ₂ , in particular

N(CH=CH ₂ ) ₂ , N(CH ₂ CH=CH ₂ ) ₂ .

According to still another embodiment of formula I, R ¹⁰ is , NH(C ₂ -C4-alkynyl), in particular NH(C ≡CH), NH(CH ₂ C≡CH).

According to still another embodiment of formula I, R ¹⁰ is _, N(C ₂ -C4-alkynyl) ₂ , in particular N(C= CH) ₂ , N(CH ₂ C≡CH) ₂ .

According to still another embodiment of formula I, R ¹⁰ is , NH(C ₃ -C6-cycloalkyl), in particular NH(C ₃ H ₇ ), NH(C ₄ H ₉ ).

According to still another embodiment of formula I, R ¹⁰ is , N(C ₃ -C6-cycloalkyl) ₂ , in particular N(C ₃ H ₇ ) ₂ , N(C ₄ H ₉ ) ₂ .

According to still another embodiment of formula I, R ¹⁰ is N(Ci-C4-alkyl)(C ₂ -C4-alkenyl), in particular N(CH ₃ )(CH=CH ₂ ), N(CH ₃ )(CH ₂ CH=CH ₂ ), N(C ₂ H ₅ )(CH=CH ₂ ), N(C ₂ H ₅ )(CH ₂ CH=CH ₂ ).

According to still another embodiment of formula I, R ¹⁰ is N(Ci-C4-alkyl)(C ₂ -C4-alkynyl), in particular N(CH ₃ )(C≡CH), N(CH ₃ )(CH ₂ C≡CH), N(C ₂ H ₅ )(C≡CH), N(C ₂ H ₅ )(CH ₂ C≡CH).

According to still another embodiment of formula I, R ¹⁰ is N(Ci-C4-alkyl)(C ₃ -C6-cycloalkyl), in particular N(CH ₃ )(C ₃ H ₇ ), N(CH ₃ )(C ₄ H ₉ ), N(C ₂ H ₅ )(C ₃ H ₇ ), N(CH ₃ )(C ₄ H ₉ ).

According to still another embodiment of formula I, R ¹⁰ is N(C ₂ -C4-alkenyl)(C ₂ -C4-alkynyl), in particular N(CH=CH ₂ )(C≡CH), N(CH ₂ CH=CH ₂ )(CH ₂ C≡CH), N(CH=CH ₂ )(C≡CH),

N(CH ₂ CH=CH ₂ )(CH ₂ C≡CH).

According to still another embodiment of formula I, R ¹⁰ is N(C ₂ -C4-alkenyl)(C ₃ -C6-cycloalkyl), in particular N(CH=CH ₂ )(C ₃ H ₇ ), N(CH ₂ CH=CH ₂ )(C ₄ H ₉ ), N(CH=CH ₂ )(C ₃ H ₇ ), N(CH ₂ CH=CH ₂ )(C ₄ H ₉ ).

According to still another embodiment of formula I, R ¹⁰ is N(C ₂ -C4-alkynyl)(C ₃ -C6-cycloalkyl), in particular N(C≡CH)(C ₃ H ₇ ), N(CH ₂ C≡CH)(C ₄ H ₉ ), N(C≡CH)(C ₃ H ₇ ), N(CH ₂ C≡CH)(C ₄ H ₉ ).

According to still another embodiment of formula I, R ¹⁰ is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH ₃ ), NH(C(=0)(C ₂ H ₅ ).

According to still another embodiment of formula I, R ¹⁰ is N(C(=0)(Ci-C4-alkyl) ₂ , in particular N(C(=0)(CH ₃ ) ₂ , N(C(=0)(C ₂ H ₅ ) ₂ .

According to a further specific embodiment of formula I, R ¹⁰ is NH-S0 ₂ -R ^x such as NH-S0 ₂ - CH ₃ , NH-S0 ₂ -CH ₂ -CH ₃ , NH-S0 ₂ -CF ₃ , NH-S0 ₂ -Ts.

According to still another embodiment of formula I, R ¹⁰ is S(0)n-Ci-C6-alkyl such as SCH ₃ , S(=0) CH ₃ , S(0) ₂ CH ₃ .

According to still another embodiment of formula I, R ¹⁰ is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0) ₂ phenyl.

According to still another embodiment of formula I, R ¹⁰ is S(0)n-C ₂ -C6-alkenyl such as

SCH=CH ₂ , S(=0)CH=CH ₂ , S(0) ₂ CH=CH ₂ , SCH ₂ CH=CH ₂ , S(=0)CH ₂ CH=CH ₂ ,

S(0) ₂ CH ₂ CH=CH ₂ . According to still another embodiment of formula I, R ¹⁰ is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0) ₂ C≡CH, SCH ₂ C≡CH, S(=0)CH ₂ C≡CH, S(0) ₂ CH ₂ C≡CH.

According to a further specific embodiment of formula I, R ¹⁰ is CH(=0).

According to a further specific embodiment of formula I, R ¹⁰ is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C ₂ H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ¹⁰ is C(=0)C ₂ -C6-alkenyl, C(=0)0(C ₂ - Ce-alkenyl) or C(=0)NH(C ₂ -C ₆ -alkenyl), wherein alkenyl is CH=CH ₂ , C(CH ₃ )=CH ₂ , CH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I, R ¹⁰ is C(=0)C ₂ -C6-alkynyl, C(=0)0(C ₂ - Ce-alkynyl) or C(=0)NH(C ₂ -C ₆ -alkynyl), wherein alkynyl is C≡CH, CH ₂ C≡CH,

According to a further specific embodiment of formula I, R ¹⁰ is C(=0)C3-C6-cycloalkyl,

C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C ₄ H ₉ ).

According to a further specific embodiment of formula I, R ¹⁰ is CH(=S).

According to a further specific embodiment of formula I, R ¹⁰ is C(=S)CrC ₆ -alkyl, wherein alkyl is CH3, C ₂ H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to a further specific embodiment of formula I, R ¹⁰ is C(=S)C ₂ -C6-alkenyl, wherein alkenyl is CH=CH ₂ , CH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I, R ¹⁰ is C(=S)C ₂ -C6-alkynyl, wherein al- kynyl is C≡CH, CH ₂ C≡CH.

According to a further specific embodiment of formula I, R ¹⁰ is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C ₄ H ₉ ).

According to a further specific embodiment of formula I, R ¹⁰ is C(=S)NHCrC ₆ -alkyl, wherein alkyl is CH3, C ₂ H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

According to still another embodiment of formula I, R ¹⁰ is Ci-C6-alkyl, in particular Ci-C ₄ -alkyl, such as CH3. or C ₂ H5, in particular CH3 or CH ₂ CH3.

According to still another embodiment of formula I, R ¹⁰ is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF ₃ , CCI ₃ , FCH ₂ , CICH ₂ , F ₂ CH, CI ₂ CH, CF ₃ CH ₂ , CCI ₃ CH ₂ or CF ₂ CHF ₂ . According to still a further embodiment of formula I, R ¹⁰ is C ₂ -C6-alkenyl, in particular C ₂ -C ₄ -alk- enyl, such as CH=CH ₂ .

According to a further specific embodiment of formula I, R ¹⁰ is C ₂ -C6-halogenalkenyl, in particular C ₂ -C ₄ -halogenalkenyl, more specifically C ₂ -C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF ₂ , CH=CCI ₂ , CH ₂ CH=CHF, CH ₂ CH=CHCI, CH ₂ CH=CF ₂ , CH ₂ CH=CCI ₂ , CF ₂ CH=CF ₂ , CCI ₂ CH=CCI ₂ , CF ₂ CF=CF ₂ , CCI ₂ CCI=CCI ₂ .

According to still a further embodiment of formula I, R ¹⁰ is C ₂ -C6-alkynyl or C ₂ -C6-halogen- alkynyl, in particular C ₂ -C ₄ -alkynyl or C ₂ -C ₄ -halogenalkynyl, such as C CH, CH ₂ C CH, C CCI, CH ₂ C≡CCI, or CCI ₂ C≡CCI.

According to a further specific embodiment of formula I, R ¹⁰ is OR ^Y wherein R ^Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C ₂ -C6-alkenyl, C ₂ -C6-halogenalkenyl, C ₂ -C6-al kynyl, C ₂ -C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.

According to a further specific embodiment of formula I, R ¹⁰ is OR ^Y , wherein R ^Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R ¹⁰ is such as OCH3 or OCH2CH3.

According to a further specific embodiment of formula I, R ¹⁰ is OR ^Y , wherein R ^Y is Ci-C6-halo- genalkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R ¹⁰ is such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI2.

According to a further specific embodiment of formula I, R ¹⁰ is OR ^Y , wherein R ^Y C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R ¹⁰ is such as OCH=CH2,

OCH ₂ CH=CH ₂ .

According to a further specific embodiment of formula I, R ¹⁰ is OR ^Y , wherein R ^Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R ¹⁰ is such as OC≡CH, OC≡CCI, OCH ₂ C≡CCI, or OCCI ₂ C≡CCI According to still another embodiment of formula I R ¹⁰ is OR ^Y wherein R ^Y is C3-C6-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R ¹⁰ is OR ^Y , wherein R ^Y is C3-C6-halogency- cloalkyl. In a special embodiment R ¹ is fully or partially halogenated cyclopropyl.

According to still another embodiment of formula I, R ¹⁰ is is OR ^Y , wherein R ^Y C3-C6-cycloalkenyl, in particular cyclopropenyl.

According to still another embodiment of formula I, R ¹⁰ is C3-C6-cycloalkyl, in particular cyclopropyl.

According to still another embodiment of formula I, R ¹⁰ is C3-C6-halogencycloalkyl. In a special embodiment R ^10b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl

According to still another embodiment of formula I, R ¹⁰ is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted by identical or different groups R ^10b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF ₃ and OCF ₃ . According to one embodiment, R ¹⁰ is unsubstituted phenyl. According to another embodiment, R ¹⁰ is phenyl, that is substituted by one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.

According to still another embodiment of formula I, R ¹⁰ is a 5-membered heteroaryl such as pyr- rol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl. According to still another embodiment of formula I , R ⁹ is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.

According to still another embodiment of formula I , R ¹⁰ is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R ¹⁰ are unsubstituted or substituted with identical or different groups R ^10a as defined and preferably defined herein, and wherein the carbocy- clic, phenyl and heteroaryl moieties of R ¹⁰ are unsubstituted or substituted with identical or dif- ferent groups R ^10b as defined and preferably defined herein.

According to still another embodiment of formula I , R ¹⁰ is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R ¹⁰ are unsubstituted or substituted with iden- tical or different groups R ^10a as defined and preferably defined herein, and wherein the cycloal- kyl moieties of R ¹⁰ are unsubstituted or substituted with identical or different groups R ^10b as defined and preferably defined herein.

R ^10a are the possible substituents for the acyclic moieties of R ⁹ .

According to one embodiment R ^10a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or substituted by substituents R ^91a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.

According to one embodiment R ^10a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R ^10a is

independently selected from F, CI, Br, I , Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1-Cl2-cyclopropyl and Ci-C2-halogenalkoxy.

According to still another embodiment of formula I , R ^10a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.

R ^10b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R ¹⁰ . R ^10b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.

According to one embodiment thereof R ^10b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R ^10b is independently selected from F, CI, CN, CH ₃ , OCH ₃ and halogenmethoxy.

Particularly preferred embodiments of R ¹⁰ according to the invention are in Table P14 below, wherein each line of lines P14-1 to P14-43 corresponds to one particular embodiment of the in- vention, wherein P14-1 to P14-43 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R ¹⁰ is bound is marked with "#" in the drawings.

Table P14:

According to still another embodiment of formula I, R ⁹ , R ¹⁰ together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaro- matic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent R ^N selected from Ci-C4-alkyl, Ci- C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted by substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R ¹¹ )m wherein m is 0, 1 , 2, 3 or 4;

R ^N is the substituent of the heteroatom N that is contained in the heterocycle formed by R ⁹ and R ¹⁰ in some of the inventive compounds. R ^N is selected from Ci-C4-alkyl, Ci-C4-halogen- alkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one, two or three substituents selected from Ci-C4-alkyl. In one preferred embodiment, R ^N is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and SC>2Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl substituents. In one particular embod- iment, R ^N is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, R ^N is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted by one methyl.

According to still another embodiment of formula I, R ⁹ and R ¹⁰ together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.

According to one embodiment, R ⁹ and R ¹⁰ form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ . According to one embodiment, R ⁹ and R ¹⁰ form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 5-membered saturated heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

According to one embodiment, R ⁹ and R ¹⁰ form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R ¹¹ . According to still another embodiment of formula I, it is substituted by R ¹¹ .

R ¹¹ according to the invention is in each case independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C ₆ -alkenyl, C ₂ -C ₆ - alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein

R ^x is Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x11 independently selected from Ci-C ₄ -alkyl, halogen, OH, CN, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy;

wherein the acyclic moieties of R ¹¹ are unsubstituted or substituted with identical or different groups R ^11a which independently of one another are selected from:

R ^11a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C ₄ -halo- genalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^111a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkoxy, CN, C3-C6-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci-C ₄ -alkylthio;

wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R ¹¹ are unsubstituted or substituted with identical or different groups R ^11b which independently of one another are selected from:

R ^11b halogen, OH, CN, Ci-C ₄ -alkyl, Ci-C ₄ -alkoxy, Ci-C ₄ -halogenalkyl, C ₃ -C ₆ -cycloalkyl, C ₃ -C ₆ - halogencycloalkyl, Ci-C ₄ -halogenalkoxy and Ci-C6-alkylthio.

For every R ¹¹ that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R ¹¹ that may be present in the ring.

According to one embodiment of formula I, wherein m is 0, 1 , 2, 3 or 4. According to still another embodiment of formula l,m is 0.

According to still another embodiment of formula I, m is 1 .

According to still another embodiment of formula I, m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.

According to one embodiment of formula I, R ¹¹ is halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci- Ce-alkoxy or , C C ₆ -halogenalkoxy, in particular CH ₃ , Et, CHF ₂ , OCH ₃ , OCHF ₂ , OCF ₃ , F, CI, more specifically H, CH ₃ , F or CI most preferred F or CI.

According to still another embodiment of formula I, R ¹¹ is halogen, in particular Br, F or CI, more specifically F or CI.

According to still another embodiment of formula I, R ¹¹ is OH.

According to still another embodiment of formula I, R ¹¹ is CN.

According to still another embodiment of formula I R ¹¹ is Nhb, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-R ^X , wherein R ^x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted by one, two, three, four or five substituents R ^x11 independently selected from Ci-C4-al- kyl.

According to still another embodiment of formula I, R ¹¹ is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH ₃ .

According to still another embodiment of formula I, R ¹¹ is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF ₃ , CHF ₂ , CH ₂ F, CCI ₃ , CHCI2 or CH ₂ CI.

According to still another embodiment of formula I, R ¹¹ is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH ₃ )=CH2,

CH ₂ CH=CH ₂ , CH=CHF, CH=CHCI, CH=CF ₂ , CH=CCI ₂ , CF=CF ₂ , CCI=CCI ₂ , CH ₂ CH=CHF, CH ₂ CH=CHCI, CH ₂ CH=CF ₂ , CH ₂ CH=CCI ₂ , CH ₂ CF=CF ₂ , CH ₂ CCI=CCI ₂ , CF ₂ CF=CF ₂ or

CCI ₂ CCI=CCI ₂ .

According to still another embodiment of formula I, R ¹¹ is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C ₂ -C ₄ -alkynyl or C ₂ -C ₄ -halogenalkynyl, such as C≡CH, CH ₂ C≡CH, C≡C-CI, C≡C- CH ₃ , CH ₂ C≡CH, CH ₂ C≡CCI or CH ₂ C≡C-CH ₃ .

According to still another embodiment of formula I, R ¹¹ is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH ₃ or OCH2CH ₃ .

According to still another embodiment of formula I, R ¹¹ is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF ₃ , OCHF ₂ , OCH ₂ F, OCCI ₃ , OCHC or OCH2CI, in particular OCF ₃ , OCHF ₂ , OCCI ₃ or OCHCI ₂ .

According to still another embodiment of formula I R ¹¹ is C3-C6-cycloalkyl, in particular cyclopro- pyl.

According to still another embodiment of formula I, R ¹¹ is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted by one, two, three or up to the maximum possible number of identical or different groups R ^11b as defined and preferably herein.

According to still another embodiment of formula I, R ¹¹ is C3-C6-halogencycloalkyl. In a special embodiment R ¹¹ is fully or partially halogenated cyclopropyl.

According to still another embodiment of formula I, R ¹¹ is unsubstituted aryl or aryl that is substituted by one, two, three or four R ^11b , as defined herein. In particular, R ¹¹ is unsubstituted phenyl or phenyl that is substituted by one, two, three or four R ^{11 b} , as defined herein.

According to still another embodiment of formula I, R ¹¹ is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R ¹¹ is 5- or 6-membered heteroaryl that is substituted by one, two or three R ^11b , as defined herein.

According to still another embodiment of formula I, R ¹¹ is in each case independently selected from halogen, OH, CN, N0 ₂ , SH, NH ₂ , NH(Ci-C ₄ -alkyl), N(Ci-C ₄ -alkyl) ₂ , NH-S0 ₂ -R ^x , Ci-C ₆ -alkyl, C ₂ -C6-alkenyl, C ₂ -C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R ¹¹ are not further substituted or carry one, two, three, four or five identical or different groups R ^11a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R ¹¹ are not further substituted or carry one, two, three, four or five identical or different groups R ^{11 b} as defined below.

According to still another embodiment of formula I, R ¹¹ is independently selected from halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci-C ₄ -halogenalkoxy.

R ^11a are the possible substituents for the acyclic moieties of R ¹¹ .

R ^11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^111a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, CrC ₄ -halogenalkyl, CrC ₄ -alkoxy, Ci-C ₄ - halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ -alkylthio.

R ^11a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C ₄ -halogenalkoxy, Ci-C6-alkylthio and phenoxy, wherein the phenyl group is unsubstituted or unsubstituted or substituted with R ^111a selected from the group consisting of halogen, OH, Ci-C ₄ -alkyl, Ci-C ₄ -halogenalkyl, Ci-C ₄ -alkoxy and Ci- C ₄ -halogenalkoxy, in particular selected from halogen, Ci-C ₂ -alkyl, Ci-C ₂ -halogenalkyl, Ci-C ₂ - alkoxy, Ci-C ₂ -halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.

In to one embodiment R ^11a is independently selected from halogen, OH, CN, Ci-C ₂ -alkoxy, C ₃ - C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C ₂ -halogenalkoxy. Specifically, R ^11a is

independently selected from F, CI, OH, CN, Ci-C ₂ -alkoxy, cyclopropyl, 1-F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F ₂ -cyclopropyl, 1 ,1-CI ₂ -cyclopropyl and Ci-C ₂ -halogenalkoxy.

According to one embodiment R ^11a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.

According to still another embodiment of formula I, R ^11a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C ₂ -halogenalkoxy. Specifically, R ^11a is

independently selected from OH, cyclopropyl and Ci-C ₂ -halogenalkoxy.

R ^11b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R ¹¹ .

R ^{11 b} according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.

According to one embodiment thereof R ^{11 b} is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C ₃ -C6-cycloalkyl, C ₃ -C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R ^{11 b} is independently selected from F, CI, OH, CN, CH ₃ , OCH ₃ , cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 , 1 -F2-cyclopropyl, 1 , 1 -Cl2-cyclopropyl and halogenmethoxy.

According to still another embodiment thereof R ^{11 b} is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy. Specifically, R ^{11 b} is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH ₃ , OCH ₃ , cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 , 1 -F ₂ -cyclopropyl, 1 , 1 -Cl2-cyclopropyl cyclopropyl and OCHF ₂ .

Particularly preferred embodiments of combinations of R ⁹ and R ¹⁰ according to the invention are in Table P35 below, wherein each line of lines P35-1 to P35-305 corresponds to one particular embodiment of the invention, wherein P35-1 to P35-305 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R ⁹ bound is marked with * in the drawings and the carbon atom, to which R ¹⁰ is bound is marked with # in the drawings. cPr stands for cyclopropyl.

Table P35:

line R ⁹ R10 line R ⁹ R10

P35-25 F CHF ₂ P35-55 Br Br

P35-26 F CFs P35-56 Br CHs

P35-27 F OCHs P35-57 Br CH2CH3

P35-28 F OChbF P35-58 Br CH ₂ F

P35-29 F OCHF2 P35-59 Br CHF ₂

P35-30 F OCFs P35-60 Br CFs

P35-31 F cPr P35-61 Br OCHs

P35-32 F C≡CH P35-62 Br OCH2F

P35-33 F CN P35-63 Br OCHF2

P35-34 F S-CHs P35-64 Br OCFs

P35-35 CI H P35-65 Br cPr

P35-36 CI F P35-66 Br C≡CH

P35-37 CI CI P35-67 Br CN

P35-38 CI Br P35-68 Br S-CHs

P35-39 CI CHs P35-69 CHs H

P35-40 CI CH2CH3 P35-70 CHs F

P35-41 CI CH ₂ F P35-71 CHs CI

P35-42 CI CHF ₂ P35-72 CHs Br

P35-43 CI CFs P35-73 CHs CHs

P35-44 CI OCHs P35-74 CHs CH2CH3

P35-45 CI OCH2F P35-75 CHs CH ₂ F

P35-46 CI OCHF2 P35-76 CHs CHF ₂

P35-47 CI OCFs P35-77 CHs CFs

P35-48 CI cPr P35-78 CHs OCHs

P35-49 CI C≡CH P35-79 CHs OCH2F

P35-50 CI CN P35-80 CHs OCHF2

P35-51 CI S-CHs P35-81 CHs OCFs

P35-52 Br H P35-82 CHs cPr

P35-53 Br F P35-83 CHs C≡CH

P35-54 Br CI P35-84 CHs CN line R ⁹ R10 line R ⁹ R10

P35-85 CHs S-CH3 P35-1 15 CH ₂ F OCF3

P35-86 CH2CH3 H P35-1 16 CH ₂ F cPr

P35-87 CH2CH3 F P35-1 17 CH ₂ F C≡CH

P35-88 CH2CH3 CI P35-1 18 CH ₂ F CN

P35-89 CH2CH3 Br P35-1 19 CH ₂ F S-CH3

P35-90 CH2CH3 CH ₃ P35-120 CHF ₂ H

P35-91 CH2CH3 CH2CH3 P35-121 CHF ₂ F

P35-92 CH2CH3 CH ₂ F P35-122 CHF ₂ CI

P35-93 CH2CH3 CHF ₂ P35-123 CHF ₂ Br

P35-94 CH2CH3 CF ₃ P35-124 CHF ₂ CH ₃

P35-95 CH2CH3 OCH3 P35-125 CHF ₂ CH2CH3

P35-96 CH2CH3 OCH2F P35-126 CHF ₂ CH ₂ F

P35-97 CH2CH3 OCHF2 P35-127 CHF ₂ CHF ₂

P35-98 CH2CH3 OCF3 P35-128 CHF ₂ CF ₃

P35-99 CH2CH3 cPr P35-129 CHF ₂ OCH3

P35-100 CH2CH3 C≡CH P35-130 CHF ₂ OCH2F

P35-101 CH2CH3 CN P35-131 CHF ₂ OCHF2

P35-102 CH2CH3 S-CH3 P35-132 CHF ₂ OCF3

P35-103 CH ₂ F H P35-133 CHF ₂ cPr

P35-104 CH ₂ F F P35-134 CHF ₂ C≡CH

P35-105 CH ₂ F CI P35-135 CHF ₂ CN

P35-106 CH ₂ F Br P35-136 CHF ₂ S-CH3

P35-107 CH ₂ F CH ₃ P35-137 CF ₃ H

P35-108 CH ₂ F CH2CH3 P35-138 CF ₃ F

P35-109 CH ₂ F CH ₂ F P35-139 CF ₃ CI

P35-1 10 CH ₂ F CHF ₂ P35-140 CF ₃ Br

P35-1 1 1 CH ₂ F CF ₃ P35-141 CF ₃ CH ₃

P35-1 12 CH ₂ F OCH3 P35-142 CF ₃ CH2CH3

P35-1 13 CH ₂ F OCH2F P35-143 CF ₃ CH ₂ F

P35-1 14 CH ₂ F OCHF2 P35-144 CF ₃ CHF ₂ line R ⁹ R10 line R ⁹ R10

P35-145 CFs CFs P35-175 OCH2F CHs

P35-146 CFs OCHs P35-176 OCH2F CH2CH3

P35-147 CFs OCH2F P35-177 OCH2F CH ₂ F

P35-148 CFs OCHF2 P35-178 OCH2F CHF ₂

P35-149 CFs OCFs P35-179 OCH2F CFs

P35-150 CFs cPr P35-180 OCH2F OCHs

P35-151 CFs C≡CH P35-181 OCH2F OCH2F

P35-152 CFs CN P35-182 OCH2F OCHF2

P35-153 CFs S-CHs P35-183 OCH2F OCFs

P35-154 OCHs H P35-184 OCH2F cPr

P35-155 OCHs F P35-185 OCH2F C≡CH

P35-156 OCHs CI P35-186 OCH2F CN

P35-157 OCHs Br P35-187 OCH2F S-CHs

P35-158 OCHs CHs P35-188 OCHF2 H

P35-159 OCHs CH2CH3 P35-189 OCHF2 F

P35-160 OCHs CH ₂ F P35-190 OCHF2 CI

P35-161 OCHs CHF ₂ P35-191 OCHF2 Br

P35-162 OCHs CFs P35-192 OCHF2 CHs

P35-163 OCHs OCHs P35-193 OCHF2 CH2CH3

P35-164 OCHs OCH2F P35-194 OCHF2 CH ₂ F

P35-165 OCHs OCHF2 P35-195 OCHF2 CHF ₂

P35-166 OCHs OCFs P35-196 OCHF2 CF ₃

P35-167 OCHs cPr P35-197 OCHF2 OCHs

P35-168 OCHs C≡CH P35-198 OCHF2 OCH2F

P35-169 OCHs CN P35-199 OCHF2 OCHF2

P35-170 OCHs S-CHs P35-200 OCHF2 OCFs

P35-171 OCH ₂ F H P35-201 OCHF2 cPr

P35-172 OCH2F F P35-202 OCHF2 C≡CH

P35-173 OCH2F CI P35-203 OCHF2 CN

P35-174 OCH2F Br P35-204 OCHF2 S-CHs line R ⁹ R10 line R ⁹ R10

P35-205 OCFs H P35-235 cPr cPr

P35-206 OCFs F P35-236 cPr C≡CH

P35-207 OCFs CI P35-237 cPr CN

P35-208 OCFs Br P35-238 cPr S-CHs

P35-209 OCFs CHs P35-239 C≡CH H

P35-210 OCFs CH2CH3 P35-240 C≡CH F

P35-21 1 OCFs CH ₂ F P35-241 C≡CH CI

P35-212 OCFs CHF ₂ P35-242 C≡CH Br

P35-213 OCFs CFs P35-243 C≡CH CHs

P35-214 OCFs OCHs P35-244 C≡CH CH2CH3

P35-215 OCFs OCH2F P35-245 C≡CH CH ₂ F

P35-216 OCFs OCHF2 P35-246 C≡CH CHF ₂

P35-217 OCFs OCFs P35-247 C≡CH CFs

P35-218 OCFs cPr P35-248 C≡CH OCHs

P35-219 OCFs C≡CH P35-249 C≡CH OCH2F

P35-220 OCFs CN P35-250 C≡CH OCH F2

P35-221 OCFs S-CHs P35-251 C≡CH OCFs

P35-222 cPr H P35-252 C≡CH cPr

P35-223 cPr F P35-253 C≡CH C≡CH

P35-224 cPr CI P35-254 C≡CH CN

P35-225 cPr Br P35-255 C≡CH S-CHs

P35-226 cPr CHs P35-256 CN H

P35-227 cPr CH2CH3 P35-257 CN F

P35-228 cPr CH ₂ F P35-258 CN CI

P35-229 cPr CHF ₂ P35-259 CN Br

P35-230 cPr CFs P35-260 CN CHs

P35-231 cPr OCHs P35-261 CN CH2CH3

P35-232 cPr OCH2F P35-262 CN CH ₂ F

P35-233 cPr OCHF2 P35-263 CN CHF ₂

P35-234 cPr OCFs P35-264 CN CFs

Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1 .B, 1-1.C, I- 1.D, 1-1 . E, 1-1. F, 1-1 .G, 1-1.1; I-2.A, 1-2. B, I-2.C, 1-2. D, I-2.E, 1-2. F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, 1-3. E, I-3.F, I-3.G, 1-3.1; I-4.A, 1-4. B, I-4.C, 1-4. D, I-4.E, 1-4. F, I-4.G, 1-4.1. In these formulae, the substituents R ⁴ , R ⁹ and R ¹⁰ are independently as defined in claim 1 or preferably defined bel

1-1.1

1-1. G 1-1. H

-2. G 1-2. H

-3. G 1-3. H

I-4.G I-4.H

Particular embodiments of the compounds I are the following compounds: 1-1.A, 1-1. B, 1-1. C, I- 1.D, 1-1 . E, 1-1 . F, 1-1. G, 1-1.1; I-2.A, I-2.B, I-2.C, I-2.D, I-2.E, I-2.F, I-2.G, 1-2.1; I-3.A, I-3.B, I-3.C, I- 3.D, I-3.E, I-3.F, I-3.G, 1-3.1; I-4.A, I-4.B, I-4.C, I-4.D, I-4.E, I-4.F, I-4.G, 1-4.1. that are compiled in the Tables 1-1 to 1 -8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9-8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.

Table 1-1 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -1.A-1 to 1-1 .A.1 -1.A-287, compounds I-2.A.1-

1. A-1 to I-2.A.1 -1.A-287, compounds I-3.A.1-1.A-1 to I-3.A.1 -1 .A-287 compounds I-4.A.1-1.A-1 to I-4.A.1-1. A-287).

Table 1-2 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -2.A-1 to 1-1 .A.1 -2.A-287, compounds I-2.A.1-

2. A-1 to I-2.A.1 -2.A-287, compounds I-3.A.1-2.A-1 to I-3.A.1 -2.A-287 compounds I-4.A.1-2.A-1 to I-4.A.1-2.A-287). Table 1-3 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -3.A-1 to 1-1 .A.1 -3.A-287, compounds I-2.A.1- 3.A-1 to I-2.A.1 -3.A-287, compounds I-3.A.1-3.A-1 to I-3.A.1 -3.A-287 compounds I-4.A.1-3.A-1 to I-4.A.1-3.A-287).

Table 1-4 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -4.A-1 to 1-1 .A.1-4.A-287, compounds I-2.A.1 -4.A-1 to I- 2.A.1-4.A-287, compounds I-3.A.1-4.A-1 to I-3.A.1 -4.A-287 compounds I-4.A.1-4.A-1 to I-4.A.1 - 4.A-287).

Table 1-5 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -5.A-1 to 1-1 .A.1 -5.A-287, compounds I-2.A.1- 5.A-1 to I-2.A.1 -5.A-287, compounds I-3.A.1-5.A-1 to I-3.A.1 -5.A-287 compounds I-4.A.1-5.A-1 to I-4.A.1-5.A-287).

Table 1-6 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1-6.A-1 to I-1.A.1 -6.A-287, compounds I- 2.A.1-6.A-1 to I-2.A.1-6.A-287, compounds I-3.A.1-6.A-1 to I-3.A.1-6.A-287 compounds I-4.A.1- 6.A-1 to I-4.A.1 -6.A-287).

Table 1-7 Compounds of the formula 1-1. A, I-2.A, I-3.A, I-4.A in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .A.1 -7.A-1 to 1-1 .A.1-7.A-287, compounds I-2.A.1 -7.A-1 to I- 2.A.1-7.A-287, compounds I-3.A.1-7.A-1 to I-3.A.1 -7.A-287 compounds I-4.A.1-7.A-1 to I-4.A.1 - 7.A-287).

Table 1-8 Compounds of the formula 1-1.A, I-2.A, I-3.A, I-4.A in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.A.1 -8.A-1 to 1-1 .A.1 -8.A-287, compounds I-2.A.1- 8.A-1 to I-2.A.1 -8.A-287, compounds I-3.A.1-8.A-1 to I-3.A.1 -8.A-287 compounds I-4.A.1-8.A-1 to I-4.A.1-8.A-287).

Table 2-1 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-1.A-1 to 1-1 .B.2-1.A-287, compounds I-2.B.2- 1.A-1 to I-2.B.2-1.A-287, compounds I-3. B.2-1.A-1 to I-3.B.2-1 .A-287 compounds I-4. B.2-1.A-1 to I-4. B.2-1. A-287).

Table 2-2 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-2.A-1 to 1-1 .B.2-2.A-287, compounds I-2.B.2- 2.A-1 to I-2.B.2-2.A-287, compounds I-3.B.2-2.A-1 to I-3.B.2-2.A-287 compounds I-4.B.2-2.A-1 to I-4.B.2-2.A-287). Table 2-3 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-3.A-1 to 1-1 .B.2-3.A-287, compounds I-2.B.2- 3.A-1 to I-2.B.2-3.A-287, compounds I-3.B.2-3.A-1 to I-3.B.2-3.A-287 compounds I-4.B.2-3.A-1 to I-4.B.2-3.A-287).

Table 2-4 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-4.A-1 to 1-1 .B.2-4.A-287, compounds I-2.B.2-4.A-1 to I- 2.B.2-4.A-287, compounds I-3.B.2-4.A-1 to I-3.B.2-4.A-287 compounds I-4.B.2-4.A-1 to I-4.B.2- 4.A-287).

Table 2-5 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-5.A-1 to 1-1 .B.2-5.A-287, compounds I-2.B.2- 5.A-1 to I-2.B.2-5.A-287, compounds I-3.B.2-5.A-1 to I-3.B.2-5.A-287 compounds I-4.B.2-5.A-1 to I-4.B.2-5.A-287).

Table 2-6 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-6.A-1 to 1-1.B.2-6.A-287, compounds I- 2.B.2-6.A-1 to I-2.B.2-6.A-287, compounds I-3.B.2-6.A-1 to I-3.B.2-6.A-287 compounds I-4.B.2- 6.A-1 to I-4.B.2-6.A-287).

Table 2-7 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .B.2-7.A-1 to I-1 .B.2-7.A-287, compounds I-2.B.2-7.A-1 to I- 2.B.2-7.A-287, compounds I-3.B.2-7.A-1 to I-3.B.2-7.A-287 compounds I-4.B.2-7.A-1 to I-4.B.2- 7.A-287).

Table 2-8 Compounds of the formula 1-1.B, I-2.B, I-3.B, I-4.B in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.B.2-8.A-1 to 1-1 .B.2-8.A-287, compounds I-2.B.2- 8.A-1 to I-2.B.2-8.A-287, compounds I-3.B.2-8.A-1 to I-3.B.2-8.A-287 compounds I-4.B.2-8.A-1 to I-4.B.2-8.A-287).

Table 3-1 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-1 .A-1 to 1-1.C.3-1.A-287, compounds I-2.C.3-

1. A-1 to I-2.C.3-1. A-287, compounds I-3.C.3-1.A-1 to I-3.C.3-1.A-287 compounds I-4.C.3-1.A-1 to I-4. C.3-1 .A-287).

Table 3-2 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-2.A-1 to 1-1.C.3-2.A-287, compounds I-2.C.3-

2. A-1 to I-2.C.3-2.A-287, compounds I-3.C.3-2.A-1 to I-3.C.3-2.A-287 compounds I-4.C.3-2.A-1 to I-4.C.3-2.A-287).

Table 3-3 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-3.A-1 to 1-1.C.3-3.A-287, compounds I-2.C.3- 3.A-1 to I-2.C.3-3.A-287, compounds I-3.C.3-3.A-1 to I-3.C.3-3.A-287 compounds I-4.C.3-3.A-1 to I-4.C.3-3.A-287).

Table 3-4 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-4.A-1 to I-1.C.3-4.A-287, compounds I-2.C.3-4.A-1 to I- 2.C.3-4.A-287, compounds I-3.C.3-4.A-1 to I-3.C.3-4.A-287 compounds I-4.C.3-4.A-1 to I-4.C.3- 4.A-287).

Table 3-5 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-5.A-1 to 1-1.C.3-5.A-287, compounds I-2.C.3- 5.A-1 to I-2.C.3-5.A-287, compounds I-3.C.3-5.A-1 to I-3.C.3-5.A-287 compounds I-4.C.3-5.A-1 to I-4.C.3-5.A-287).

Table 3-6 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-6.A-1 to 1-1.C.3-6.A-287, compounds I- 2.C.3-6.A-1 to I-2.C.3-6.A-287, compounds I-3.C.3-6.A-1 to I-3.C.3-6.A-287 compounds I-4.C.3-

6. A-1 to I-4.C.3-6.A-287).

Table 3-7 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .C.3-7.A-1 to I-1.C.3-7.A-287, compounds I-2.C.3-7.A-1 to I- 2.C.3-7.A-287, compounds I-3.C.3-7.A-1 to I-3.C.3-7.A-287 compounds I-4.C.3-7.A-1 to I-4.C.3-

7. A-287).

Table 3-8 Compounds of the formula 1-1.C, I-2.C, I-3.C, I-4.C in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.C.3-8.A-1 to 1-1.C.3-8.A-287, compounds I-2.C.3- 8.A-1 to I-2.C.3-8.A-287, compounds I-3.C.3-8.A-1 to I-3.C.3-8.A-287 compounds I-4.C.3-8.A-1 to I-4.C.3-8.A-287).

Table 4-1 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-1 .A-1 to 1-1.D.4-1.A-287, compounds I-2.D.4-

1. A-1 to I-2.D.4-1. A-287, compounds I-3.D.4-1.A-1 to I-3.D.4-1.A-287 compounds I-4.D.4-1.A-1 to I-4. D.4-1 .A-287).

Table 4-2 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-2.A-1 to 1-1.D.4-2.A-287, compounds I-2.D.4-

2. A-1 to I-2.D.4-2.A-287, compounds I-3.D.4-2.A-1 to I-3.D.4-2.A-287 compounds I-4.D.4-2.A-1 to I-4.D.4-2.A-287).

Table 4-3 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-3.A-1 to 1-1.D.4-3.A-287, compounds I-2.D.4- 3.A-1 to I-2.D.4-3.A-287, compounds I-3.D.4-3.A-1 to I-3.D.4-3.A-287 compounds I-4.D.4-3.A-1 to I-4.D.4-3.A-287).

Table 4-4 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-4.A-1 to I-1.D.4-4.A-287, compounds I-2.D.4-4.A-1 to I- 2.D.4-4.A-287, compounds I-3.D.4-4.A-1 to I-3.D.4-4.A-287 compounds I-4.D.4-4.A-1 to I-4.D.4- 4.A-287).

Table 4-5 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-5.A-1 to 1-1.D.4-5.A-287, compounds I-2.D.4- 5.A-1 to I-2.D.4-5.A-287, compounds I-3.D.4-5.A-1 to I-3.D.4-5.A-287 compounds I-4.D.4-5.A-1 to I-4.D.4-5.A-287).

Table 4-6 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-6.A-1 to 1-1.D.4-6.A-287, compounds I- 2.D.4-6.A-1 to I-2.D.4-6.A-287, compounds I-3.D.4-6.A-1 to I-3.D.4-6.A-287 compounds I-4.D.4-

6. A-1 to I-4.D.4-6.A-287).

Table 4-7 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .D.4-7.A-1 to I-1.D.4-7.A-287, compounds I-2.D.4-7.A-1 to I- 2.D.4-7.A-287, compounds I-3.D.4-7.A-1 to I-3.D.4-7.A-287 compounds I-4.D.4-7.A-1 to I-4.D.4-

7. A-287).

Table 4-8 Compounds of the formula 1-1.D, I-2.D, I-3.D, I-4.D in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.D.4-8.A-1 to 1-1.D.4-8.A-287, compounds I-2.D.4- 8.A-1 to I-2.D.4-8.A-287, compounds I-3.D.4-8.A-1 to I-3.D.4-8.A-287 compounds I-4.D.4-8.A-1 to I-4.D.4-8.A-287).

Table 5-1 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-1.A-1 to 1-1 .E.5-1.A-287, compounds I-2.E.5-

1. A-1 to I-2.E.5-1.A-287, compounds I-3. E.5-1. A-1 to I-3.E.5-1 .A-287 compounds I-4. E.5-1. A-1 to I-4. E.5-1. A-287).

Table 5-2 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-2.A-1 to 1-1 .E.5-2.A-287, compounds I-2.E.5-

2. A-1 to I-2.E.5-2.A-287, compounds I-3.E.5-2.A-1 to I-3.E.5-2.A-287 compounds I-4.E.5-2.A-1 to I-4.E.5-2.A-287).

Table 5-3 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-3.A-1 to 1-1 .E.5-3.A-287, compounds I-2.E.5- 3.A-1 to I-2.E.5-3.A-287, compounds I-3.E.5-3.A-1 to I-3.E.5-3.A-287 compounds I-4.E.5-3.A-1 to I-4.E.5-3.A-287).

Table 5-4 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-4.A-1 to 1-1 .E.5-4.A-287, compounds I-2.E.5-4.A-1 to I- 2.E.5-4.A-287, compounds I-3.E.5-4.A-1 to I-3.E.5-4.A-287 compounds I-4.E.5-4.A-1 to I-4.E.5- 4.A-287).

Table 5-5 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-5.A-1 to 1-1 .E.5-5.A-287, compounds I-2.E.5- 5.A-1 to I-2.E.5-5.A-287, compounds I-3.E.5-5.A-1 to I-3.E.5-5.A-287 compounds I-4.E.5-5.A-1 to I-4.E.5-5.A-287).

Table 5-6 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-6.A-1 to 1-1.E.5-6.A-287, compounds I- 2.E.5-6.A-1 to I-2.E.5-6.A-287, compounds I-3.E.5-6.A-1 to I-3.E.5-6.A-287 compounds I-4.E.5-

6. A-1 to I-4.E.5-6.A-287).

Table 5-7 Compounds of the formula 1-1. E, I-2.E, I-3.E, I-4.E in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .E.5-7.A-1 to 1-1 .E.5-7.A-287, compounds I-2.E.5-7.A-1 to I- 2.E.5-7.A-287, compounds I-3.E.5-7.A-1 to I-3.E.5-7.A-287 compounds I-4.E.5-7.A-1 to I-4.E.5-

7. A-287).

Table 5-8 Compounds of the formula 1-1.E, I-2.E, I-3.E, I-4.E in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.E.5-8.A-1 to 1-1 .E.5-8.A-287, compounds I-2.E.5- 8.A-1 to I-2.E.5-8.A-287, compounds I-3.E.5-8.A-1 to I-3.E.5-8.A-287 compounds I-4.E.5-8.A-1 to I-4.E.5-8.A-287).

Table 6-1 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R ⁹ is CH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1 .F.1-1.A-1 to I-1.F.1-1.A-287, compounds I-2.F.1-1 .A-1 to I- 2.F.1 -1 .A-287, compounds I-3.F.1-1.A-1 to I-3.F.1-1 .A-287 compounds I-4.F.1 -1 .A-1 to I-4.F.1 - 1.A-287).

Table 6-2 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-2.A-1 to 1-1 .F.1 -2.A-287, compounds I-2.F.1 - 2.A-1 to I-2.F.1-2.A-287, compounds I-3.F.1 -2.A-1 to I-3.F.1 -2.A-287 compounds I-4.F.1-2.A-1 to I-4.F.1 -2.A-287). Table 6-3 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-3.A-1 to 1-1 .F.1 -3.A-287, compounds I-2.F.1 - 3.A-1 to I-2.F.1-3.A-287, compounds I-3.F.1 -3.A-1 to I-3.F.1 -3.A-287 compounds I-4.F.1-3.A-1 to I-4.F.1 -3.A-287).

Table 6-4 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-4.A-1 to I-1.F.1-4.A-287, compounds I-2.F.1-4.A-1 to I- 2.F.1 -4.A-287, compounds I-3.F.1-4.A-1 to I-3.F.1-4.A-287 compounds I-4.F.1 -4.A-1 to I-4.F.1 - 4.A-287).

Table 6-5 Compounds of the formula 1-1.F, I-2.F, I-3.F, I-4.F in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-5.A-1 to 1-1 .F.1 -5.A-287, compounds I-2.F.1 - 5.A-1 to I-2.F.1-5.A-287, compounds I-3.F.1 -5.A-1 to I-3.F.1 -5.A-287 compounds I-4.F.1-5.A-1 to I-4.F.1 -5.A-287).

Table 6-6 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.F.1-6.A-1 to 1-1.F.1-6.A-287, compounds I- 2.F.1 -6.A-1 to I-2.F.1 -6.A-287, compounds I-3.F.1-6.A-1 to I-3.F.1-6.A-287 compounds I-4.F.1 - 6.A-1 to I-4.F.1-6.A-287).

Table 6-7 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.F.1-7.A-1 to I-1.F.1-7.A-287, compounds I-2.F.1 -7.A-1 to I-2.F.1 - 7.A-287, compounds I-3.F.1 -7.A-1 to I-3.F.1 -7.A-287 compounds I-4.F.1-7.A-1 to I-4.F.1-7.A- 287).

Table 6-8 Compounds of the formula 1-1. F, I-2.F, I-3.F, I-4.F in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .F.1-8.A-1 to I-1.F.1-8.A-287, compounds I-2.F.1-8.A-1 to I- 2.F.1 -8.A-287, compounds I-3.F.1-8.A-1 to I-3.F.1-8.A-287 compounds I-4.F.1 -8.A-1 to I-4.F.1 - 8.A-287).

Table 7-1 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-1.A-1 to 1-1 .G.7-1.A-287, compounds I-2.G.7-

1. A-1 to I-2.G.7-1.A-287, compounds I-3.G.7-1.A-1 to I-3.G.7-1 .A-287 compounds I-4.G.7-1.A-1 to I-4. G.7-1.A-287).

Table 7-2 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-2.A-1 to 1-1 .G.7-2.A-287, compounds I-2.G.7-

2. A-1 to I-2.G.7-2.A-287, compounds I-3.G.7-2.A-1 to I-3.G.7-2.A-287 compounds I-4.G.7-2.A-1 to I-4.G.7-2.A-287).

Table 7-3 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-3.A-1 to 1-1 .G.7-3.A-287, compounds I-2.G.7-

3. A-1 to I-2.G.7-3.A-287, compounds I-3.G.7-3.A-1 to I-3.G.7-3.A-287 compounds I-4.G.7-3.A-1 to I-4.G.7-3.A-287).

Table 7-4 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-4.A-1 to I-1.G.7-4.A-287, compounds I-2.G.7-4.A-1 to I- 2.G.7-4.A-287, compounds I-3.G.7-4.A-1 to I-3.G.7-4.A-287 compounds I-4.G.7-4.A-1 to I-

4. G.7-4.A-287).

Table 7-5 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-5.A-1 to 1-1 .G.7-5.A-287, compounds I-2.G.7-

5. A-1 to I-2.G.7-5.A-287, compounds I-3.G.7-5.A-1 to I-3.G.7-5.A-287 compounds I-4.G.7-5.A-1 to I-4.G.7-5.A-287).

Table 7-6 Compounds of the formula 1-1. G, I-2.G, I-3.G, I-4.G in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-6.A-1 to 1-1.G.7-6.A-287, compounds I- 2.G.7-6.A-1 to I-2.G.7-6.A-287, compounds I-3.G.7-6.A-1 to I-3.G.7-6.A-287 compounds I- 4.G.7-6.A-1 to I-4.G.7-6.A-287).

Table 7-7 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .G.7-7.A-1 to I-1.G.7-7.A-287, compounds I-2.G.7-7.A-1 to I- 2.G.7-7.A-287, compounds I-3.G.7-7.A-1 to I-3.G.7-7.A-287 compounds I-4.G.7-7.A-1 to I- 4.G.7-7.A-287).

Table 7-8 Compounds of the formula 1-1.G, I-2.G, I-3.G, I-4.G in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.G.7-8.A-1 to 1-1 .G.7-8.A-287, compounds I-2.G.7- 8.A-1 to I-2.G.7-8.A-287, compounds I-3.G.7-8.A-1 to I-3.G.7-8.A-287 compounds I-4.G.7-8.A-1 to I-4.G.7-8.A-287).

Table 8-1 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-1 .A-1 to 1-1.H.8-1.A-287, compounds I-2.H.8-

1. A-1 to I-2.H.8-1. A-287, compounds I-3.H.8-1.A-1 to I-3.H.8-1.A-287 compounds I-4.H.8-1.A-1 to I-4.H.8-1 .A-287).

Table 8-2 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.H.8-2.A-1 to 1-1.H.8-2.A-287, compounds I-2.H.8-

2. A-1 to I-2.H.8-2.A-287, compounds I-3.H.8-2.A-1 to I-3.H.8-2.A-287 compounds I-4.H.8-2.A-1 to I-4.H.8-2.A-287).

Table 8-3 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-3.A-1 to 1-1.H.8-3.A-287, compounds I-2.H.8-

3. A-1 to I-2.H.8-3.A-287, compounds I-3.H.8-3.A-1 to I-3.H.8-3.A-287 compounds I-4.H.8-3.A-1 to I-4.H.8-3.A-287).

Table 8-4 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is Br and the mean- ing for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-4.A-1 to I-1.H.8-4.A-287, compounds I-2.H.8-4.A-1 to I- 2.H.8-4.A-287, compounds I-3.H.8-4.A-1 to I-3.H.8-4.A-287 compounds I-4.H.8-4.A-1 to I-4.H.8-

4. A-287).

Table 8-5 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-5.A-1 to 1-1.H.8-5.A-287, compounds I-2.H.8-

5. A-1 to I-2.H.8-5.A-287, compounds I-3.H.8-5.A-1 to I-3.H.8-5.A-287 compounds I-4.H.8-5.A-1 to I-4.H.8-5.A-287).

Table 8-6 Compounds of the formula 1-1. H, I-2.H, I-3.H, I-4.H in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-6.A-1 to 1-1.H.8-6.A-287, compounds I- 2.H.8-6.A-1 to I-2.H.8-6.A-287, compounds I-3.H.8-6.A-1 to I-3.H.8-6.A-287 compounds I-4.H.8-

6. A-1 to I-4.H.8-6.A-287).

Table 8-7 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is H and the mean- ing for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-7.A-1 to I-1.H.8-7.A-287, compounds I-2.H.8-7.A-1 to I- 2.H.8-7.A-287, compounds I-3.H.8-7.A-1 to I-3.H.8-7.A-287 compounds I-4.H.8-7.A-1 to I-4.H.8-

7. A-287).

Table 8-8 Compounds of the formula 1-1.H, I-2.H, I-3.H, I-4.H in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .H.8-8.A-1 to 1-1.H.8-8.A-287, compounds I-2.H.8-

8. A-1 to I-2.H.8-8.A-287, compounds I-3.H.8-8.A-1 to I-3.H.8-8.A-287 compounds I-4.H.8-8.A-1 to I-4.H.8-8.A-287).

Table 9-1 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is CH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-1 .A-1 to 1-1.1.9-1 .A-287, compounds 1-2.1.9-1 .A-1 to I-2.I.9- 1.A-287, compounds 1-3.1.9-1. A-1 to 1-3.1.9-1 .A-287 compounds 1-4.1.9-1.A-1 to 1-4.1.9-1 .A-287).

Table 9-2 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-2.A-1 to 1-1.1.9-2.A-287, compounds I-2.I.9-2.A-1 to I- 2.I.9-2.A-287, compounds I-3.I.9-2.A-1 to I -3.1.9-2. A-287 compounds I-4.I.9-2.A-1 to I-4.I.9-2.A- 287).

Table 9-3 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-3.A-1 to 1-1.1.9-3.A-287, compounds I-2.I.9-3.A-1 to I- 2.I.9-3.A-287, compounds I-3.I.9-3.A-1 to I-3.I.9-3.A-287 compounds I-4.I.9-3.A-1 to I-4.I.9-3.A- 287).

Table 9-4 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-4.A-1 to I-1.I.9-4.A-287, compounds I-2.I.9-4.A-1 to I-2.I.9- 4.A-287, compounds I-3.I.9-4.A-1 to I-3.I.9-4.A-287 compounds I-4.I.9-4.A-1 to I-4.I.9-4.A-287).

Table 9-5 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1 .1.9-5.A-1 to I-1.I.9-5.A-287, compounds I-2.I.9-5.A-1 to I- 2.I.9-5.A-287, compounds I-3.I.9-5.A-1 to I-3.I.9-5.A-287 compounds I-4.I.9-5.A-1 to I-4.I.9-5.A- 287).

Table 9-6 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds 1-1.1.9-6.A-1 to 1-1 .1.9-6.A-287, compounds I-2.I.9-6.A-1 to I-2.I.9-6.A-287, compounds I-3.I.9-6.A-1 to I-3.I.9-6.A-287 compounds I-4.I.9-6.A-1 to I-4.I.9- 6.A-287).

Table 9-7 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-7.A-1 to I-1.I.9-7.A-287, compounds I-2.I.9-7.A-1 to I-2.I.9-

7. A-287, compounds I-3.I.9-7.A-1 to I-3.I.9-7.A-287 compounds I-4.I.9-7.A-1 to I-4.I.9-7.A-287). Table 9-8 Compounds of the formula 1-1.1, 1-2.1, 1-3.1, 1-4.1 in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds I-1.I.9-8.A-1 to I-1.I.9-8.A-287, compounds I-2.I.9-8.A-1 to I-2.I.9-

8. A-287, compounds I-3.I.9-8.A-1 to I-3.I.9-8.A-287 compounds I-4.I.9-8.A-1 to I-4.I.9-8.A-287). Particular embodiments of the compounds I are the following compounds: X-1.A, X-1.B, X-1 .C, X-1 .D, X-1.E, X-1 .F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.I; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.I; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.I. In these formulae, the substituents R ³ , R ⁴ , R ⁹ and R ¹⁰ are independently as defined in claim 1 or preferably defined below:

X-1.G X-1.H

X-2.G X-2.H

X-3.1

X-3.G X-3.

X-4.G X-4.H

Particular embodiments of the compounds I are the following compounds: X-1 .A, X-1 .B, X-1.C, X-1 .D, X-1.E, X-1.F, X-1.G, X-1.1; X-2.A, X-2.B, X-2.C, X-2.D, X-2.E, X-2.F, X-2.G, X-2.1; X-3.A, X-3.B, X-3.C, X-3.D, X-3.E, X-3.F, X-3.G, X-3.1; X-4.A, X-4.B, X-4.C, X-4.D, X-4.E, X-4.F, X-4.G, X-4.1. that are compiled in the Tables 1 -1 to 1-8, Tables 2-1 to 2-8, Tables 3-1 to 3-8, Tables 4-1 to 4-8, Tables 5-1 to 5-8, Tables 6-1 to 6-8, Tables 7-1 to 7-8, Tables 8-1 to 8-8, Tables 9-1 to 9- 8. Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.

Table 1-1 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-1.A-1 to X-1.A.1 -1 .A-287, compounds X-2.A.1 -

1. A-1 to X-2.A.1 -1.A-287, compounds X-3.A.1-1 .A-1 to X-3. A.1-1. A-287 compounds X-4.A.1- 1.A-1 to X-4. A.1-1. A-287).

Table 1-2 Compounds of the formula X-1 .A, X-2.A, X-3.A, X-4.A in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .A.1-2.A-1 to X-1.A.1 -2.A-287, compounds X-2.A.1 -

2. A-1 to X-2.A.1 -2.A-287, compounds X-3.A.1-2.A-1 to X-3.A.1-2.A-287 compounds X-4.A.1- 2.A-1 to X-4.A.1-2.A-287). Table 1-3 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-3.A-1 to X-1.A.1-3.A-287, compounds X-2.A.1-

3. A-1 to X-2.A.1-3.A-287, compounds X-3.A.1-3.A-1 to X-3.A.1-3.A-287 compounds X-4.A.1- 3.A-1 to X-4.A.1-3.A-287).

Table 1-4 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-4.A-1 to X-1.A.1 -4.A-287, compounds X-2.A.1-

4. A-1 to X-2.A.1-4.A-287, compounds X-3.A.1-4.A-1 to X-3.A.1-4.A-287 compounds X-4.A.1- 4.A-1 to X-4.A.1-4.A-287).

Table 1-5 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-5.A-1 to X-1.A.1-5.A-287, compounds X-2.A.1-

5. A-1 to X-2.A.1-5.A-287, compounds X-3.A.1-5.A-1 to X-3.A.1-5.A-287 compounds X-4.A.1- 5.A-1 to X-4.A.1-5.A-287).

Table 1-6 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-6.A-1 to X-1.A.1-6.A-287, compounds X- 2.A.1-6.A-1 to X-2.A.1-6.A-287, compounds X-3.A.1-6.A-1 to X-3.A.1-6.A-287 compounds X- 4.A.1-6.A-1 to X-4.A.1-6.A-287).

Table 1-7 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-7.A-1 to X-1.A.1 -7.A-287, compounds X-2.A.1-

7. A-1 to X-2.A.1-7.A-287, compounds X-3.A.1-7.A-1 to X-3.A.1-7.A-287 compounds X-4.A.1- 7.A-1 to X-4.A.1-7.A-287).

Table 1-8 Compounds of the formula X-1.A, X-2.A, X-3.A, X-4.A in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.A.1-8.A-1 to X-1.A.1-8.A-287, compounds X-2.A.1-

8. A-1 to X-2.A.1-8.A-287, compounds X-3.A.1-8.A-1 to X-3.A.1-8.A-287 compounds X-4.A.1- 8.A-1 to X-4.A.1-8.A-287).

Table 2-1 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-1.A-1 to X-1.B.2-1.A-287, compounds X-2.B.2- 1.A-1 to X-2.B.2-1.A-287, compounds X-3. B.2-1.A-1 to X-3. B.2-1.A-287 compounds X-4.B.2-

1. A-1 to X-4. B.2-1. A-287).

Table 2-2 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-2.A-1 to X-1.B.2-2.A-287, compounds X-2.B.2- 2.A-1 to X-2.B.2-2.A-287, compounds X-3.B.2-2.A-1 to X-3.B.2-2.A-287 compounds X-4.B.2-

2. A-1 to X-4.B.2-2.A-287). Table 2-3 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-3.A-1 to X-1.B.2-3.A-287, compounds X-2.B.2-

3. A-1 to X-2.B.2-3.A-287, compounds X-3.B.2-3.A-1 to X-3.B.2-3.A-287 compounds X-4.B.2- 3.A-1 to X-4.B.2-3.A-287).

Table 2-4 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-4.A-1 to X-1.B.2-4.A-287, compounds X-2.B.2-

4. A-1 to X-2.B.2-4.A-287, compounds X-3.B.2-4.A-1 to X-3.B.2-4.A-287 compounds X-4.B.2- 4.A-1 to X-4.B.2-4.A-287).

Table 2-5 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-5.A-1 to X-1.B.2-5.A-287, compounds X-2.B.2-

5. A-1 to X-2.B.2-5.A-287, compounds X-3.B.2-5.A-1 to X-3.B.2-5.A-287 compounds X-4.B.2- 5.A-1 to X-4.B.2-5.A-287).

Table 2-6 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-6.A-1 to X-1.B.2-6. A-287, compounds X- 2.B.2-6.A-1 to X-2.B.2-6.A-287, compounds X-3.B.2-6.A-1 to X-3.B.2-6.A-287 compounds X- 4.B.2-6.A-1 to X-4.B.2-6.A-287).

Table 2-7 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-7.A-1 to X-1.B.2-7.A-287, compounds X-2.B.2-

7. A-1 to X-2.B.2-7.A-287, compounds X-3.B.2-7.A-1 to X-3.B.2-7.A-287 compounds X-4.B.2- 7.A-1 to X-4.B.2-7.A-287).

Table 2-8 Compounds of the formula X-1.B, X-2.B, X-3.B, X-4.B in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.B.2-8.A-1 to X-1.B.2-8.A-287, compounds X-2.B.2-

8. A-1 to X-2.B.2-8.A-287, compounds X-3.B.2-8.A-1 to X-3.B.2-8.A-287 compounds X-4.B.2- 8.A-1 to X-4.B.2-8.A-287).

Table 3-1 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-1.A-1 to X-1.C.3-1.A-287, compounds X-2.C.3- 1.A-1 to X-2. C.3-1.A-287, compounds X-3. C.3-1.A-1 to X-3.C.3-1.A-287 compounds X-4.C.3-

1. A-1 to X-4. C.3-1.A-287).

Table 3-2 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-2.A-1 to X-1.C.3-2.A-287, compounds X-2.C.3-

2. A-1 to X-2.C.3-2.A-287, compounds X-3.C.3-2.A-1 to X-3.C.3-2.A-287 compounds X-4.C.3- 2. A-1 to X-4.C.3-2.A-287).

Table 3-3 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-3.A-1 to X-1.C.3-3.A-287, compounds X-2.C.3- 3.A-1 to X-2.C.3-3.A-287, compounds X-3.C.3-3.A-1 to X-3.C.3-3.A-287 compounds X-4.C.3-

3. A-1 to X-4.C.3-3.A-287).

Table 3-4 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-4.A-1 to X-1.C.3-4.A-287, compounds X-2.C.3- 4.A-1 to X-2.C.3-4.A-287, compounds X-3.C.3-4.A-1 to X-3.C.3-4.A-287 compounds X-4.C.3-

4. A-1 to X-4.C.3-4.A-287).

Table 3-5 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-5.A-1 to X-1.C.3-5.A-287, compounds X-2.C.3- 5.A-1 to X-2.C.3-5.A-287, compounds X-3.C.3-5.A-1 to X-3.C.3-5.A-287 compounds X-4.C.3-

5. A-1 to X-4.C.3-5.A-287).

Table 3-6 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-6.A-1 to X-1.C.3-6.A-287, compounds X- 2.C.3-6.A-1 to X-2.C.3-6.A-287, compounds X-3.C.3-6.A-1 to X-3.C.3-6.A-287 compounds X- 4.C.3-6.A-1 to X-4.C.3-6.A-287).

Table 3-7 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-7.A-1 to X-1.C.3-7.A-287, compounds X-2.C.3- 7.A-1 to X-2.C.3-7.A-287, compounds X-3.C.3-7.A-1 to X-3.C.3-7.A-287 compounds X-4.C.3-

7. A-1 to X-4.C.3-7.A-287).

Table 3-8 Compounds of the formula X-1.C, X-2.C, X-3.C, X-4.C in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.C.3-8.A-1 to X-1.C.3-8.A-287, compounds X-2.C.3- 8.A-1 to X-2.C.3-8.A-287, compounds X-3.C.3-8.A-1 to X-3.C.3-8.A-287 compounds X-4.C.3-

8. A-1 to X-4.C.3-8.A-287).

Table 4-1 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-1.A-1 to X-1.D.4-1.A-287, compounds X-2.D.4- 1.A-1 to X-2. D.4-1.A-287, compounds X-3. D.4-1.A-1 to X-3. D.4-1.A-287 compounds X-4.D.4-

1. A-1 to X-4. D.4-1.A-287).

Table 4-2 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-2.A-1 to X-1.D.4-2.A-287, compounds X-2.D.4-

2. A-1 to X-2.D.4-2.A-287, compounds X-3.D.4-2.A-1 to X-3.D.4-2.A-287 compounds X-4.D.4- 2. A-1 to X-4.D.4-2.A-287).

Table 4-3 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-3.A-1 to X-1.D.4-3.A-287, compounds X-2.D.4- 3.A-1 to X-2.D.4-3.A-287, compounds X-3.D.4-3.A-1 to X-3.D.4-3.A-287 compounds X-4.D.4-

3. A-1 to X-4.D.4-3.A-287).

Table 4-4 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-4.A-1 to X-1.D.4-4.A-287, compounds X-2.D.4- 4.A-1 to X-2.D.4-4.A-287, compounds X-3.D.4-4.A-1 to X-3.D.4-4.A-287 compounds X-4.D.4-

4. A-1 to X-4.D.4-4.A-287).

Table 4-5 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-5.A-1 to X-1.D.4-5.A-287, compounds X-2.D.4- 5.A-1 to X-2.D.4-5.A-287, compounds X-3.D.4-5.A-1 to X-3.D.4-5.A-287 compounds X-4.D.4-

5. A-1 to X-4.D.4-5.A-287).

Table 4-6 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-6.A-1 to X-1.D.4-6.A-287, compounds X- 2.D.4-6.A-1 to X-2.D.4-6.A-287, compounds X-3.D.4-6.A-1 to X-3.D.4-6.A-287 compounds X- 4.D.4-6.A-1 to X-4.D.4-6.A-287).

Table 4-7 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-7.A-1 to X-1.D.4-7.A-287, compounds X-2.D.4- 7.A-1 to X-2.D.4-7.A-287, compounds X-3.D.4-7.A-1 to X-3.D.4-7.A-287 compounds X-4.D.4-

7. A-1 to X-4.D.4-7.A-287).

Table 4-8 Compounds of the formula X-1.D, X-2.D, X-3.D, X-4.D in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.D.4-8.A-1 to X-1.D.4-8.A-287, compounds X-2.D.4- 8.A-1 to X-2.D.4-8.A-287, compounds X-3.D.4-8.A-1 to X-3.D.4-8.A-287 compounds X-4.D.4-

8. A-1 to X-4.D.4-8.A-287).

Table 5-1 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-1.A-1 to X-1.E.5-1.A-287, compounds X-2.E.5- 1.A-1 to X-2.E.5-1.A-287, compounds X-3.E.5-1.A-1 to X-3. E.5-1. A-287 compounds X-4.E.5-

1. A-1 to X-4. E.5-1. A-287).

Table 5-2 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-2.A-1 to X-1.E.5-2.A-287, compounds X-2.E.5-

2. A-1 to X-2.E.5-2.A-287, compounds X-3.E.5-2.A-1 to X-3.E.5-2.A-287 compounds X-4.E.5- 2. A-1 to X-4.E.5-2.A-287).

Table 5-3 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-3.A-1 to X-1.E.5-3.A-287, compounds X-2.E.5- 3.A-1 to X-2.E.5-3.A-287, compounds X-3.E.5-3.A-1 to X-3.E.5-3.A-287 compounds X-4.E.5-

3. A-1 to X-4.E.5-3.A-287).

Table 5-4 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-4.A-1 to X-1.E.5-4.A-287, compounds X-2.E.5- 4.A-1 to X-2.E.5-4.A-287, compounds X-3.E.5-4.A-1 to X-3.E.5-4.A-287 compounds X-4.E.5-

4. A-1 to X-4.E.5-4.A-287).

Table 5-5 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-5.A-1 to X-1.E.5-5.A-287, compounds X-2.E.5- 5.A-1 to X-2.E.5-5.A-287, compounds X-3.E.5-5.A-1 to X-3.E.5-5.A-287 compounds X-4.E.5-

5. A-1 to X-4.E.5-5.A-287).

Table 5-6 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-6.A-1 to X-1.E.5-6.A-287, compounds X- 2.E.5-6.A-1 to X-2.E.5-6.A-287, compounds X-3.E.5-6.A-1 to X-3.E.5-6.A-287 compounds X- 4.E.5-6.A-1 to X-4.E.5-6.A-287).

Table 5-7 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-7.A-1 to X-1.E.5-7.A-287, compounds X-2.E.5- 7.A-1 to X-2.E.5-7.A-287, compounds X-3.E.5-7.A-1 to X-3.E.5-7.A-287 compounds X-4.E.5-

7. A-1 to X-4.E.5-7.A-287).

Table 5-8 Compounds of the formula X-1.E, X-2.E, X-3.E, X-4.E in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.E.5-8.A-1 to X-1.E.5-8.A-287, compounds X-2.E.5- 8.A-1 to X-2.E.5-8.A-287, compounds X-3.E.5-8.A-1 to X-3.E.5-8.A-287 compounds X-4.E.5-

8. A-1 to X-4.E.5-8.A-287).

Table 6-1 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-1.A-1 to X-1.F.1-1.A-287, compounds X-2.F.1- 1.A-1 to X-2.F.1-1.A-287, compounds X-3.F.1-1.A-1 to X-3.F.1-1.A-287 compounds X-4.F.1-

1. A-1 to X-4.F.1-1.A-287).

Table 6-2 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-2.A-1 to X-1.F.1-2.A-287, compounds X-2.F.1-

2. A-1 to X-2.F.1-2.A-287, compounds X-3.F.1-2.A-1 to X-3.F.1-2.A-287 compounds X-4.F.1- 2. A-1 to X-4.F.1-2.A-287).

Table 6-3 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-3.A-1 to X-1.F.1-3.A-287, compounds X-2.F.1- 3.A-1 to X-2.F.1-3.A-287, compounds X-3.F.1-3.A-1 to X-3.F.1-3.A-287 compounds X-4.F.1-

3. A-1 to X-4.F.1-3.A-287).

Table 6-4 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-4.A-1 to X-1.F.1-4.A-287, compounds X-2.F.1- 4.A-1 to X-2.F.1-4.A-287, compounds X-3.F.1-4.A-1 to X-3.F.1-4.A-287 compounds X-4.F.1-

4. A-1 to X-4.F.1-4.A-287).

Table 6-5 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-5.A-1 to X-1.F.1-5.A-287, compounds X-2.F.1- 5.A-1 to X-2.F.1-5.A-287, compounds X-3.F.1-5.A-1 to X-3.F.1-5.A-287 compounds X-4.F.1-

5. A-1 to X-4.F.1-5.A-287).

Table 6-6 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-6.A-1 to X-1.F.1-6.A-287, compounds X- 2.F.1-6.A-1 to X-2.F.1-6.A-287, compounds X-3.F.1-6.A-1 to X-3.F.1-6.A-287 compounds X- 4.F.1-6.A-1 to X-4.F.1-6.A-287).

Table 6-7 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-7.A-1 to X-1.F.1-7.A-287, compounds X-2.F.1- 7.A-1 to X-2.F.1-7.A-287, compounds X-3.F.1-7.A-1 to X-3.F.1-7.A-287 compounds X-4.F.1-

7. A-1 to X-4.F.1-7.A-287).

Table 6-8 Compounds of the formula X-1.F, X-2.F, X-3.F, X-4.F in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.F.1-8.A-1 to X-1.F.1-8.A-287, compounds X-2.F.1- 8.A-1 to X-2.F.1-8.A-287, compounds X-3.F.1-8.A-1 to X-3.F.1-8.A-287 compounds X-4.F.1-

8. A-1 to X-4.F.1-8.A-287).

Table 7-1 Compounds of the formula X-1.G, X-2.G, X-3.G, X-4.G in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-1.A-1 to X-1.G.7-1.A-287, compounds X- 2.G.7-1.A-1 to X-2.G.7-1.A-287, compounds X-3.G.7-1.A-1 to X-3. G.7-1.A-287 compounds X- 4.G.7-1.A-1 to X-4.G.7-1.A-287).

Table 7-2 Compounds of the formula X-1.G, X-2.G, X-3.G, X-4.G in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-2.A-1 to X-1.G.7-2.A-287, compounds X- 2.G.7-2.A-1 to X-2.G.7-2.A-287, compounds X-3.G.7-2.A-1 to X-3.G.7-2.A-287 compounds X- 4.G.7-2.A-1 to X-4.G.7-2.A-287). Table 7-3 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.G.7-3.A-1 to X-1 .G.7-3.A-287, compounds X- 2.G.7-3.A-1 to X-2.G.7-3.A-287, compounds X-3.G.7-3.A-1 to X-3.G.7-3.A-287 compounds X- 4.G.7-3.A-1 to X-4.G.7-3.A-287).

Table 7-4 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-4.A-1 to X-1.G.7-4.A-287, compounds X- 2.G.7-4.A-1 to X-2.G.7-4.A-287, compounds X-3.G.7-4.A-1 to X-3.G.7-4.A-287 compounds X- 4.G.7-4.A-1 to X-4.G.7-4.A-287).

Table 7-5 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-5.A-1 to X-1.G.7-5.A-287, compounds X- 2.G.7-5.A-1 to X-2.G.7-5.A-287, compounds X-3.G.7-5.A-1 to X-3.G.7-5.A-287 compounds X- 4.G.7-5.A-1 to X-4.G.7-5.A-287).

Table 7-6 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-6.A-1 to X-1 .G.7-6.A-287, compounds X- 2.G.7-6.A-1 to X-2.G.7-6.A-287, compounds X-3.G.7-6.A-1 to X-3.G.7-6.A-287 compounds X- 4.G.7-6.A-1 to X-4.G.7-6.A-287).

Table 7-7 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-7.A-1 to X-1.G.7-7.A-287, compounds X- 2.G.7-7.A-1 to X-2.G.7-7.A-287, compounds X-3.G.7-7.A-1 to X-3.G.7-7.A-287 compounds X- 4.G.7-7.A-1 to X-4.G.7-7.A-287).

Table 7-8 Compounds of the formula X-1 .G, X-2.G, X-3.G, X-4.G in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .G.7-8.A-1 to X-1.G.7-8.A-287, compounds X- 2.G.7-8.A-1 to X-2.G.7-8.A-287, compounds X-3.G.7-8.A-1 to X-3.G.7-8.A-287 compounds X- 4.G.7-8.A-1 to X-4.G.7-8.A-287).

Table 8-1 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-1.A-1 to X-1.H.8-1 .A-287, compounds X-2.H.8- 1.A-1 to X-2. H.8-1 .A-287, compounds X-3. H.8-1 .A-1 to X-3. H.8-1.A-287 compounds X-4.H.8- 1. A-1 to X-4. H.8-1 .A-287).

Table 8-2 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-2.A-1 to X-1.H.8-2.A-287, compounds X-2.H.8- 2.A-1 to X-2.H.8-2.A-287, compounds X-3.H.8-2.A-1 to X-3.H.8-2.A-287 compounds X-4.H.8- 2.A-1 to X-4.H.8-2.A-287).

Table 8-3 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-3.A-1 to X-1.H.8-3.A-287, compounds X-2.H.8- 3.A-1 to X-2.H.8-3.A-287, compounds X-3.H.8-3.A-1 to X-3.H.8-3.A-287 compounds X-4.H.8-

3. A-1 to X-4.H.8-3.A-287).

Table 8-4 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-4.A-1 to X-1.H.8-4.A-287, compounds X-2.H.8-

4. A-1 to X-2. H.8-4.A-287, compounds X-3.H.8-4.A-1 to X-3.H.8-4.A-287 compounds X-4.H.8-

4. A-1 to X-4. H.8-4.A-287).

Table 8-5 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-5.A-1 to X-1.H.8-5.A-287, compounds X-2.H.8-

5. A-1 to X-2.H.8-5.A-287, compounds X-3.H.8-5.A-1 to X-3.H.8-5.A-287 compounds X-4.H.8- 5.A-1 to X-4.H.8-5.A-287).

Table 8-6 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-6.A-1 to X-1.H.8-6.A-287, compounds X- 2.H.8-6.A-1 to X-2.H.8-6.A-287, compounds X-3.H.8-6.A-1 to X-3.H.8-6.A-287 compounds X- 4.H.8-6.A-1 to X-4.H.8-6.A-287).

Table 8-7 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-7.A-1 to X-1.H.8-7.A-287, compounds X-2.H.8- 7.A-1 to X-2. H.8-7.A-287, compounds X-3.H.8-7.A-1 to X-3.H.8-7.A-287 compounds X-4.H.8-

7. A-1 to X-4. H.8-7.A-287).

Table 8-8 Compounds of the formula X-1 .H, X-2.H, X-3.H, X-4.H in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .H.8-8.A-1 to X-1.H.8-8.A-287, compounds X-2.H.8-

8. A-1 to X-2.H.8-8.A-287, compounds X-3.H.8-8.A-1 to X-3.H.8-8.A-287 compounds X-4.H.8- 8.A-1 to X-4.H.8-8.A-287).

Table 9-1 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.1 in which R ⁹ is CH ₃ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-1.A-1 to X-1 .1.9-1.A-287, compounds X-2.1.9-

1. A-1 to X-2.1.9-1.A-287, compounds X-3.1.9-1. A-1 to X-3.1.9-1 .A-287 compounds X-4.1.9-1. A-1 to X-4.1.9-1. A-287).

Table 9-2 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R ⁹ is CHF ₂ and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-2.A-1 to X-1 .1.9-2.A-287, compounds X-2.1.9-

2. A-1 to X-2.I.9-2.A-287, compounds X-3.I.9-2.A-1 to X-3.I.9-2.A-287 compounds X-4.I.9-2.A-1 to X-4.l.9-2.A-287).

Table 9-3 Compounds of the formula X-1.1, X-2.1, X-3.1, X-4.1 in which R ⁹ is C≡CH and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-3.A-1 to X-1 .1.9-3.A-287, compounds X-2.1.9-

3. A-1 to X-2.I.9-3.A-287, compounds X-3.I.9-3.A-1 to X-3.I.9-3.A-287 compounds X-4.I.9-3.A-1 to X-4.I.9-3.A-287).

Table 9-4 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R ⁹ is Br and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.I.9-4.A-1 to X-1 .1.9-4.A-287, compounds X-2.1.9-4.A-1 to X- 2.I.9-4.A-287, compounds X-3.I.9-4.A-1 to X-3.I.9-4.A-287 compounds X-4.I.9-4.A-1 to X-4.I.9-

4. A-287).

Table 9-5 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R ⁹ is OCH3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-5.A-1 to X-1 .1.9-5.A-287, compounds X-2.1.9-

5. A-1 to X-2.I.9-5.A-287, compounds X-3.I.9-5.A-1 to X-3.I.9-5.A-287 compounds X-4.I.9-5.A-1 to X-4.I.9-5.A-287).

Table 9-6 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R ⁹ is cyclopropyl and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.1.9-6.A-1 to X-1 .1.9-6.A-287, compounds X- 2.I.9-6.A-1 to X-2.I.9-6.A-287, compounds X-3.I.9-6.A-1 to X-3.I.9-6.A-287 compounds X-4.I.9-

6. A-1 to X-4.l.9-6.A-287).

Table 9-7 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R ⁹ is H and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1.I.9-7.A-1 to X-1 .1.9-7.A-287, compounds X-2.1.9-7.A-1 to X- 2.I.9-7.A-287, compounds X-3.I.9-7.A-1 to X-3.I.9-7.A-287 compounds X-4.I.9-7.A-1 to X-4.I.9-

7. A-287).

Table 9-8 Compounds of the formula X-1.1, X-2.1, X-3.I, X-4.I in which R ⁹ is CF3 and the meaning for the combination of R ⁴ and R ¹⁰ for each individual compound corresponds in each case to one line of Table A (compounds X-1 .1.9-8.A-1 to X-1 .1.9-8.A-287, compounds X-2.1.9-

8. A-1 to X-2.I.9-8.A-287, compounds X-3.I.9-8.A-1 to X-3.I.9-8.A-287 compounds X-4.I.9-8.A-1 to X-4.I.9-8.A-287).

Table A

The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.

The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.

Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.

The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring. Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural biotech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.

Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from an- other class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield ^® summer rape (Canola,

BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun ^® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady ^® (glyphosate-tolerant, Monsanto, U.S.A.), Cul- tivance ^® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink ^® (glufosinate-tolerant, Bayer CropScience, Germany).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nema- todes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdyster- oid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278,

WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coelop- tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard ^® (corn cultivars producing the Cry1 Ab toxin), YieldGard ^® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink ^® (corn cultivars producing the Cry9c toxin), Herculex ^® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothri- cin-N-acetyltransferase [PAT]); NuCOTN ^® 33B (cotton cultivars producing the Cry1 Ac toxin), Bollgard ^® I (cotton cultivars producing the CrylAc toxin), Bollgard ^® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT ^® (cotton cultivars producing a VIP-toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt-Xtra ^® , NatureGard ^® , KnockOut ^® , BiteGard ^® , Pro- tecta ^® , Bt1 1 (e. g. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogenesis- related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications mentioned above.

Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera ^® rape, DOW Agro Sciences, Canada).

Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora ^® potato, BASF SE, Germany).

The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); A/ternar/a spp. (Alternaria leaf spot) on vegetables, rape (A. brassico/a or brassi- cae), sugar beets (A tenuis), fruits, rice, soybeans, potatoes (e. g. A. so/an/ or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. (anthracnose) on wheat and A. horde/ on barley; Bipolar/s and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydisj or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokin- iana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis

(powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana. grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. bet/cola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. soro- kiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glo- merella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthrac- nose stalk rot), soft fruits, potatoes (e. g. C. coccodes. black dot), beans (e. g. C. lindemuthi- anum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cy- cloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. lirio- dendri, teleomorph: Neonectria liriodendri. Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.

phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyr- enophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis. tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formiti- poria (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Ery- siphe spp. (powdery mildew) on sugar beets {E. betae), vegetables (e. g. E. pis/), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. gra- minearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. so/ani( sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibber- ella spp. on cereals (e. g. G. zeae) and rice (e. g. G fujikuroi. Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G gossypiion cotton; Grainstaining complex on rice; G 'uignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp . (syn. Drechslera, teleomorph: Cochiioboius) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseo/ή (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco {P. tabacina) and soybeans (e. g. P. manshurica);

Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy- soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.

megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad- leaved trees (e. g. P. ramorum. sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mil- dew) on vines and P. halstedii ^' on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets {P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapes/a yal- lundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubens/s on cucurbits or P. hum/// on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. horde/ ^' (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus sto/on/fer (b\ack mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Saro- cladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. ro/fs/ior S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum

(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucker!) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto- sphaeria [syn. Phaeosphaer/a] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. trit/c/ (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis. corn smut) and sugar cane; Venturis spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.

The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials. The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola pp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coni- ophora pp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pu/a spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp. , Trichoderma spp. , Alternaria spp. , Paecilomyces spp. and Zygomycetes such as Mucorspp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.

The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the present invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted, ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.

The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.

The term "plant health" is to be understood to denote a condition of the plant and/or its products which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may result from each other.

The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.

The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.

Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.

The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.

An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materials and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.

The compounds I, their N-oxides and salts can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), cap- sules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 ^th Ed. May 2008, CropLife International.

The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.

Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and am- photeric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, es- ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vinyl alcohols, or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.

Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.

Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e. g. alizarin-, azo- and phthalogencyanine colorants).

Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.

Examples for composition types and their preparation are:

i) Water-soluble concentrates (SL, LS)

10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.

ii) Dispersible concentrates (DC)

5-25 wt% of a compound I and 1-10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.

iii) Emulsifiable concentrates (EC)

15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesul- fonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.

iv) Emulsions (EW, EO, ES)

5-40 wt% of a compound I and 1 -10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1- 2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.

vi) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.

vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% disper- sants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.

viii) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.

ix) Microemulsion (ME)

5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid di- methyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and ar- ylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.

x) Microcapsules (CS)

An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocya- nate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 - 10 wt%. The wt% relate to the total CS composition.

xi) Dustable powders (DP, DS)

1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g. finely divided kaolin) ad 100 wt%.

xii) Granules (GR, FG)

0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.

xiii) Ultra-low volume liquids (UL)

1 -50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.

The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% col-

The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).

For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treat- ment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.

In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.

When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 .

A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant path- ogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that re- duce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.

The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemi- cal composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.

According to one embodiment, individual components of the composition according to the in- vention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.

Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal compo- sition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.

Mixing the compounds I or the compositions comprising them in the use form as fungicides with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.

The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combina- tions but does not limit them:

A) Respiration inhibitors

Inhibitors of complex III at Q ₀ site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1.2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1.4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1 .9), man- destrobin (A.1 .10), metominostrobin (A.1 .1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1.15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1 .17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymeth yl)-phenyl)-2-meth- oxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1 .20), famoxadone (A.1 .21 ), fenamidone (A.1.21 ), methyl-/V-[2-[(1 ,4-dimethyl-5-phenyl- pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1-[2-[[1 -(4-chlorophenyl)py- razol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-o ne (A.1 .25), ( 2 )-5-[1 -(2,4-di- chlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino- y3-dimethyl-pent-v3-enamide (A.1.34), (Zi2£)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-m

(A.1 .35), pyriminostrobin (A.1.36), bifujunzhi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxy- methylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38);

- inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),

[(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carb onyl)amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2, 3), fenpicoxamid (A.2.4);

- inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), ox- ycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyra- ziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), inpyrfluxam (A.3.22), /V-[(22)-2-[3-chloro-5-(2-cyclopropylethynyl)-2-pyridyl]-2-i sopropoxyimino-ethyl]-3- (difluoromethyl)-1 -methyl-pyrazole-4-carboxamide (A.3.23), fluindapyr (A.3.28), methyl (E)-2- [2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop- 2-enoate (A.3.30), isoflu- cypram (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3-carboxamide

(A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1 ,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1-dimethyl-indan-4-yl]pyridine-3-carbox- amide (A.3.39);

- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), di- nobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone

(A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);

B) Sterol biosynthesis inhibitors (SBI fungicides)

- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromucona- zole (B.1.3), cyproconazole (B.1.4), difenoconazole (B.1.5), diniconazole (B.1 .6), dinicona- zole-M (B.1 .7), epoxiconazole (B.1.8), fenbuconazole (B.1 .9), fluquinconazole (B.1.10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1 .12), hexaconazole (B.1 .13), imibenconazole (B.1.14), ipcona- zole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclobu- trazole (B.1 .20), penconazole (B.1.21 ), propiconazole (B.1 .22), prothioconazole (B.1 .23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1 .26), triadimefon (B.1 .27), triadimenol (B.1.28), triticonazole (B.1 .29), uniconazole (B.1 .30), 2-(2,4-difluorophenyl)-1 ,1 - difluoro-3-(tetrazol-1 -yl)-1 -[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31 ), 2-(2,4-difluorophenyl)-1 ,1-difluoro-3-(tetrazol-1-yl)-1 -[5-[4-(trifluoromethoxy)phenyl]-2- pyridyl]propan-2-ol (B.1.32), ipfentrifluconazole (B.1 .37), mefentrifluconazole (B.1.38), 2- (chloromethyl)-2-methyl-5-(p-tolylmethyl)-1 -(1 ,2,4-triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1 .44), pefurazoate (B.1.45), prochloraz (B.1 .46), triflumizol (B.1.47); pyrimidines, pyridines and piperazines: fenarimol (B.1 .49), pyrifenox (B.1.50), triforine (B.1.51 ), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol -4-yl]-(3-pyridyl)met nol (B.1.52);

- Delta 14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spi- roxamine (B.2.8);

- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );

- Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );

C) Nucleic acid synthesis inhibitors

- phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1 .3), metalaxyl (C.1 .4), metalaxyl-M (C.1 .5), ofurace (C.1 .6), oxadixyl (C.1 .7);

- other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);

D) Inhibitors of cell division and cytoskeleton

- tubulin inhibitors: benomyl (D.1 .1 ), carbendazim (D.1 .2), fuberidazole (D1.3), thiabendazole (D.1 .4), thiophanate-methyl (D.1 .5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1 .6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazi ne (D.1 .7), N-eth- yl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1 .9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)butanamide (D.1 .10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1 .1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanam- ide (D.1 .12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-ac etamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-pr opyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-m ethylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5 -dimethyl-pyrazol-3-amine (D.1 .16);

- other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);

E) Inhibitors of amino acid and protein synthesis

- methionine synthesis inhibitors: cyprodinil (E.1 .1 ), mepanipyrim (E.1.2), pyrimethanil (E.1.3);

- protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);

F) Signal transduction inhibitors

- MAP / histidine kinase inhibitors: fluoroimid (F.1.1 ), iprodione (F.1.2), procymidone (F.1 .3), vinclozolin (F.1 .4), fludioxonil (F.1 .5);

- G protein inhibitors: quinoxyfen (F.2.1 );

G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4);

- lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);

- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

- compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );

- inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluorome- thyl-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3, 5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperi- din-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl- pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-pi- peridyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoro- methyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.6), 4-[1- [2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N- tetralin-1 -yl-pyridine-2-carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)py- razol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-c arboxamide (G.5.9), 4-[1 -[2-[3,5- bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acet yl]-4-piperidyl]-N-tetralin- 1 -yl-pyridine-2-carboxamide (G.5.1 1 );

H) Inhibitors with Multi Site Action

- inorganic active substances: Bordeaux mixture (H.1 .1 ), copper (H.1 .2), copper acetate

(H.1 .3), copper hydroxide (H.1 .4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1 .7);

- thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam

(H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);

- organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );

- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3),

guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);

I) Cell wall synthesis inhibitors

- inhibitors of glucan synthesis: validamycin (1.1 .1 ), polyoxin B (1.1.2);

- melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (I.2.3), dicy- clomet (I.2.4), fenoxanil (I.2.5); J) Plant defence inducers

- acibenzolar-S-methyl (J.1 .1 ), probenazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadi- one-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-di- methoxyphenyl)thiadiazole-5-carboxamide (J.1 .10);

K) Unknown mode of action

- bronopol (K.1.1 ), chinomethionat (K.1 .2), cyflufenamid (K.1 .3), cymoxanil (K.1 .4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1 .9), difen- zoquat-methylsulfate (K.1 .10), diphenylamin (K.1.1 1 ), fenitropan (K.1.12), fenpyrazamine (K.1.13), flumetover (K.1.14), flusulfamide (K.1 .15), flutianil (K.1.16), harpin (K.1 .17), metha- sulfocarb (K.1 .18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21 ), oxin- copper (K.1.22), proquinazid (K.1.23), tebufloquin (K.1.24), tecloftalam (K.1 .25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phen yl)-N-ethyl-N-methyl formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phen yl)-N-eth- yl-N-methyl formamidine (K.1 .28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]- oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2- yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1 -(3,5-diflu- orophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-forma midine (K.1 .31 ), N'-[5-bromo- 6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-met hyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N -methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy )-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy) -phenyl)-N-ethyl- N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol- 5-yl]-2-prop-2-ynyloxy-acetamide (K.1 .36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin- 3-yl]-pyridine (pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]- pyridine (K.1.38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1 .40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-py ridyl]carba- mate (K.1 .42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]o xyme- thyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phe- nyl]propan-2-ol (K.1.44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]pro pan-2-ol (K.1.45), quinofumelin (K.1.47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-me- thyl-2-pyridyl]quinazoline (K.1.51 ), 3-[(3,4-dichloroisothiazol-5-yl)methoxy]-1 ,2-benzothiazole 1 ,1 -dioxide (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamid ine (K.1.53), pyrifenamine (K.1 .54);

M) Growth regulators

abscisic acid (M.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime- thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,

2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;

N) Herbicides from classes N.1 to N.15

N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim,

clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepra- loxydim, tralkoxydim, 4-(4'-chloro-4-cyclo ^-, propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopro- pyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6 H)-one (CAS 1312337- 45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tet- ramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cy- clopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3 -one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2 ^' ,4'-dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1 ); 5-(acet- yloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-

3- one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 );

4- (2 ^' ,4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-

5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS

1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-

5- 0X0-2 H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosul- furon-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu- ron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imaza- mox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, di- closulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, py- rithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino ]- benzoic acid-1-methyhethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- ny oxyJphenylJ-'methylJamirioJ-berizoic acid propyl ester (CAS 420138-40-5), N-(4-bromo- phenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanami ne (CAS 420138-01 -8); flu- carbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thien- carbazone, thiencarbazone-methyl; triafamone;

N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, pro- panil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;

N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrim- idin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-tri- fluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452098-92-9), N tetrahy- drofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-meth yl-1 H-pyrazole-1 -carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-met hyl-1 H- pyrazole-1-carboxamide (CAS 452099-05-7), N tetrahydro-"furfuryl-3-(2-chloro-6-fluoro-4- trifluoro ^-, methylphenoxy)-5-methyl-1 H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7- fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-

[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0),

1 - methyl-6-trifluoro ^-, methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dih ydro-2H-ben- zo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4-[2-chloro- 5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-

2- enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]- 1 -methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);

N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,

norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl) ^_, pyrimi- dine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintri- one, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltri- one, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon; N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potas- sium, glyphosate-trimesium (sulfosate);

N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;

N.8 DHP synthase inhibitors: asulam;

N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendi- methalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;

N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethena- mid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

II.9

II .8 N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS

175899-01-1 );

N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;

N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quin- merac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino- 3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyrid ine-2-carboxylic acid, benzyl

4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5- fluoropyridine-2-carboxylate (CAS 1390661 -72-9);

N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so- dium;

N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydra- zide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, me- thyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;

O) Insecticides from classes 0.1 to 0.29

0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, bu- tocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, aza- methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosa- lone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, pro- thiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole;

0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans- fluthrin; DDT, methoxychlor;

0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam;

4,5-dihydro-AAnitro-1-(2-oxiranylmethyl)-1 A/-imidazol-2-amine, (2£)-1-[(6-chloropyridin-3-yl)me- thylJ-AAnitro^-pentylidenehydrazinecarboximidamide; 1-[(6-chloropyridin-3-yl)methyl]-7-me- thyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; nicotine; sulfoxaflor, f I u py rad if u ron e, trif I u mezopy ri m ;

0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;

0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbe- mectin;

0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;

0.9

Chordotonal organ TRPV channel modulators: pymetrozine, pyrifluquinazon; flonicamid;

O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;

0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaeri- cus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Ba- cillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp.

kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;

0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;

0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium; 0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron, diflubenzuron, flu- cycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;

0.17 Moulting disruptors: cyromazine;

0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;

0.19 Octopamin receptor agonists: amitraz;

O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl,

fluacrypyrim, bifenazate;

0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrim- idifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;

0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyano- phenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(diflu oromethoxy)phenyl]-hydrazinecar- boxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(m ethylsulfonyl)- amino]phenyl]methylene]-hydrazinecarboxamide;

0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat, spi- ropidion;

0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium

phosphide, phosphine, zinc phosphide, cyanide;

0.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;

0.26 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cycla- niliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-l-(trifluoromethyl)- ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N1-{2-methyl-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfony lethyl)- phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)- 1 H-pyrazol-5-yl]- carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyri dyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6- methyl-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxa mide; N-[4-chloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chlo ro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba - moyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyra zole-3-carboxamide; N-[4,6-di- bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluo- romethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-meth- ylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro- 2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole- 5-carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1-(3,5-di chloro-2-pyri- dyl)-1 H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-meth- ylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; cyhalodi- amide;

7: Chordotonal organ Modulators - undefined target site: flonicamid;

8. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, broflanilide, bromopropylate, chinome- thionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, tioxazafen, 1 1-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1 -en- 10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-az aspiro[4.5]dec-3-en-2- one, 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl ]-3-(trifluoromethyl)-1 H-1 ,2,4- triazole-5-amine, Bacillus flupyrimin,fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(tri- fluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-y l)benzamide; fluxametamide; 5- [3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethyla- mino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]-6-(trifluor omethyl)phe- nyl]-2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide ; N-[3-[[[2-iodo-4-[1 ,2,2,2-tetra- fluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]car bonyl]phenyl]-N-methyl- benzamide; N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methy l-benzamide; 4-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromet hyl)phe- nyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 , 2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]-6(trifluoromethyl)phen yl]amino]carbonyl]phenyl]-N-me- thyl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(tri- fluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxa mide; 4-cyano-N-[2-cyano-5- [[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carba moyl]phenyl]-2- methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro- 4- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fl uoro-benzamide; N-[5-[[2-chloro- 6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carba moyl]-2-cyano-phe- nyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1 -(tri- fluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano -2-methyl-benzamide; N-[5- [[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carba moyl]-2- cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carba moyl]phenyl]-2-methyl-ben- zamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1-(trifluorome- thyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 ,2,2,2- tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cya no-phenyl]-4-cyano-2-methyl-ben- zamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridi- nyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimi- dine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-car boxamide; N-methylsulfonyl- 6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol- 5-yl]-3-methylthio-propanamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio - propanamide; N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methyl thio-propanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-me thylthio-propanamide; N-[4- chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylt hio-propanamide; N-[4-chloro-2- (3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanami de; N-[4-chloro-2-(3-pyridyl)thia- zol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3- methylthio-propanamide; 1 -[(6-chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy- 7-methyl-8-nitro-imidazo[1 ,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazol e- 4-carboxamide; N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide; 1 -[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin- 4-yl-pyrazole-4- carboxamide; N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide; 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; 1- [1-(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyraz ole-4-carboxamide; N-me- thyl-1-(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxa mide; 1-(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazo le-4-carboxamide; 1-(4,4-difluo- rocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carbo xamide, N-(1-methylethyl)-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-tri- fluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecar- boxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indaz ole-5-carboxamide; N- (2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxami de; 2-(3-pyridinyl )-N-(2-pyrimidi- nylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H- indazole-5-carboxamidetyclopyrazoflor; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-

3- (3,3,3-trifluoropropylsulfinyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-di- fluorocyclopropyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol- 4-yl]-3-[(2,2-difluorocyclopropyl)methylsulfinyl]-N-ethyl-pr opanamide; sarolaner, lotilaner, /V- [4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl- 3-(1 ,1 ,2,2,2-pentafluoroethyl)-

4- (trifluoromethyl)-1 A/-pyrazole-5-carboxamide; M. UN.22a 2-(3-ethylsulfonyl-2-pyridyl)-3-me- thyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]- 3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 4-[5-(3,5-dichlorophenyl)-5-(trifluorome- thyl)-4 isoxazol-3-yl]-N[(4 )-2-ethyl-3-oxo-isoxazolidin-4-yl]-2-methyl-benzamide, 4-[5- (3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4 isoxazol-3-yl]-/V-[(4 )-2-ethyl-3-oxo- isoxazolidin-4-yl]-2-methyl-benzamide; /V-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-me- thyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carbo xamide, /V-[4-chloro-3- [(1 -cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoro- methyl)pyrazole-3-carboxamide; acynonapyr; benzpyrimoxan; chloro-/V-(1 -cyanocyclopro- pyl)-5-[1-[2-methyl-5-(1 ,1 ,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyr azol-4- yl]benzamide.

The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;

EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,

JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;

US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ; WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ).

The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one further fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with individual compounds I or individual fungicides from groups A) to K).

By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).

This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.

When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1 .5 hours to 5 days, even more preferred from 2 hours to 1 day.

In the binary mixtures and compositions according to the invention the weight ratio of the component 1 ) and the component 2) generally depends from the properties of the active com- ponents used, usually it is in the range of from 1 :10,000 to 10,000:1 , often it is in the range of from 1 :100 to 100:1 , regularly in the range of from 1 :50 to 50: 1 , preferably in the range of from 1 :20 to 20:1 , more preferably in the range of from 1 :10 to 10:1 , even more preferably in the range of from 1 :4 to 4:1 and in particular in the range of from 1 :2 to 2:1.

According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1:1, often in the range of from 100: 1 to 1:1, regularly in the range of from 50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more preferably in the range of from 10:1 to 1:1, even more preferably in the range of from 4:1 to 1 :1 and in particular in the range of from 2:1 to 1:1.

According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1:1 to 1:1000, often in the range of from 1:1 to 1:100, regularly in the range of from 1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more preferably in the range of from 1:1 to 1:10, even more preferably in the range of from 1:1 to 1:4 and in particular in the range of from 1:1 to 1:2.

In the ternary mixtures, i.e. compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1 :4 to 4:1 , and the weight ratio of component 1 ) and component 3) usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1:4 to 4:1.

Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the component 1).

These ratios are also suitable for inventive mixtures applied by seed treatment. Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q ₀ site in group A), more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25 (A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34) and (A.1.35).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from compounds (A.2.1), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1 .4), (B.1 .5), (B.1 .8), (B.1 .10), (B.1.1 1 ), (B.1 .12), (B.1.13), (B.1 .17), (B.1.18), (B.1 .21 ), (B.1.22), (B.1.23), (B.1 .25), (B.1.26), (B.1 .29), (B.1.34), (B.1 .37), (B.1.38), (B.1 .43) and (B.1 .46); particularly selected from (B.1.5), (B.1.8), (B.1 .10), (B.1.17), (B.1.22), (B.1.23), (B.1 .25), (B.1.33), (B.1 .34), (B.1.37), (B.138), (B.1.43) and (B.1.46).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta 14-reductase inhibitors in group B), more preferably selected from com- pounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1 .1 ), (C.1 .2), (C.1.4) and (C.1.5); particularly selected from (C.1 .1 ) and (C.1.4).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably selected from compounds (C.2.6),(C.2.7) and (C.2.8).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1.5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1.5) and (D.2.6).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group E), more preferably selected from compounds (E.1.1 ), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1.2), (F.1.4) and (F.1.5).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1 ), (G.3.3), (G.3.6), (G.5.1 ), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.1 1 ); particularly selected from (G.3.1 ), (G.5.1 ), (G.5.2) and (G.5.3).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (I.2.5).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1 .2), (J.1.5) and (J.1 .8); in particular (J.1.5).

Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1.41 ), (K.1 .42), (K.1.44), (K.1 .45), (K.1.47) and (K.1.49); particularly selected from (K.1 .41 ), (K.1.44), (K.1 .45), (K.1.47) and (K.1 .49).

The mixtures of active substances can be prepared as compositions comprising besides the ac- tive ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.

Synthesis example

With due modification of the starting compounds, the procedures shown in the synthesis exam- pies below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.

HPLC-MS: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (5 gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1 .5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode).

Example 1 ) Synthesis of 1 -(5,6-dimethyl-3-pyridyl)-3-methyl-3-(3-pyridyl)-4H-isoquino line (1-1 )

2,0 g of trifluoromethane sulfonic acid was added dropwise to a mixture of 0,26 g (2 mmol) 5,6- dimethylpyridine-3-carbonitrile and 0,650 g (3 mmol) 1 -phenyl-2-(3-pyridyl)propan-2-ol in 50 mL dichloroethane at 0 - 5°C. After 3 h at room temperature the reaction mixture was poured onto sodium carbonate solution, the organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic extracts were extracted with sodium hydrogen carbonate and water, evaporated and the residue was purified via MPLC with water/ace- tonitrile mixtures to yield 0,1 19 g (18 %) of the title compound as a light yellow oil.

¹ H-NMR (CDCIs, δ in ppm): 8,8 ( d, 1 H); 8,6 (s, 1 H); 8,4 (d, 1 H); 7,9 (d, 1 H); 7,8 (s, 1 H); 7,4 (m, 1 H); 7,3-7,2 (m, 3H); 3,3 (d, 1 H); 3,1 (d, 1 H); 2,6 (s, 3H); 2,4 (d, 3H); 1 ,6 (s, 3H).

*HPLC-MS: Rt = 0,641 min; M ⁺ +H = 328,1

Example 2) Synthesis of 3-(3,3-dichloroallyl)-1 -[6-(difluoromethyl)-5-methyl-3-pyridyl]-3-methyl- 4H-isoquinoline (I-5)

1. Synthesis of 2-(2,2-dichlorocyclopropyl)-1 -phenyl-propan-2-ol

The mixture of 2,2-dichlorocyclopropyl methyl ketone (2,645 g, 18.8 mmol) in THF (100 mL) was added BnMgCI (56,3mL, 56,3 mmol) dropwise at 0 °C under N ₂ , the mixture was stirred for 3 h at 0 °C. The reaction mixture was quenched with aq. NH4CI (50 mL) and extracted with MTBE (50 mL), dried over Na2S0 ₄ and concentrated, the residue was purified by column

(PE:EtOAc=40:1 ) to give the tittle compound (2.7 g, 60%) as yellow oil.

H-NMR (CDCIs, δ in ppm): 1.43 - 1.54 (m, 3 H) 1 .58 (dd, J=8.38, 7.06 Hz, 1 H) 1 .65 - 1.72 (m, 1 H) 2.81 - 2.93 (m, 2H) 7.13 - 7.42 (m, 5 H)

2. Synthesis of [(1 E)-5,5-dichloro-2-methyl-penta-1 ,4-dienyl]benzene

The solution of 2-(2,2-dichlorocyclopropyl)-1-phenyl-propan-2-ol (0,4 g, 1 ,64 mmol) in toluene (20 mL) was added p-TsOH (156 mg, 0,82 mmol) under N ₂ , the solution was heated to 80 oC for 16 h. The reaction mixture was concentrated, the residue was purified by column (PE) to give the tittle compound (254 mg, crude) as colorless oil.

3. Synthesis of methyl 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1-yl]-3-met hyl-pyridine-2-car- boxylate

The solution of methyl 5-cyano-3-methyl-pyridine-2-carboxylate (105 mg, 0.6 mmol) and [(1 E)-

5.5- dichloro-2-methyl-penta-1 ,4-dienyl]benzene (270 mg, 1.2 mmol) were in DCM (20 mL) was added TfOH (450 mg, 3 mmol) dropwise at 0 oC under N2, the mixture was stirred for 1 .5 h at 0 °C. The reaction mixture was quenched with aq. NaHCC>3 (30 mL) and extracted with DCM (20 mL), the organic layer was dried over Na2S0 ₄ and concentrated, the residue was purified by Pre-TLC (PE:EtOAc=1 :1 ) to give the tittle compound (1 1 1 mg, 46%) as red oil.

¹ H-NMR (CDCIs, δ in ppm): 1.22 (s, 3 H) 2.43 - 2.58 (m, 2 H) 2.66 (s, 3 H) 2.73 - 2.93 (m, 2 H) 3.96 - 4.04 (m, 3 H), 6.01 - 6.09 (m, 1 H) 7.14 (d, J=7.50 Hz, 1 H) 7.21 - 7.28 (m, 2 H) 7.37 - 7.46 (m, 1 H) 7.85 (s, 1 H) 8.69 (s, 1 H)

4. Synthesis of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1 -yl]-3-methyl-pyridine-2- carbaldehyde

The mixture of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1-yl]-3-met hyl-pyridine-2-carbox- ylic acid (360 mg, 0,89 mmol) in DCM (20 mL) was added DIBAL-H (1 ,34 mL, 1 ,34 mmol) drop- wise at -78 °C under N2, the mixture was stirred for 1 h at -78 °C. The reaction mixture was quenched with aq. NH ₄ CI (30 mL) and extracted with DCM (30 mL), dried over Na2S0 ₄ and con- centrated to give the tittle compound (360 mg, crude) as yellow solid.

¹ H-NMR (CDCI3, δ in ppm): 2.37 (s, 5 H) 2.47 - 2.60 (m, 3 H) 2.74 (s, 3 H) 2.77 - 2.95 (m, 3 H) 6.08 (t, J=7.59 Hz, 1 H), 7.40 - 7.48 (m, 1 H) 7.85 (s, 1 H) 8.83 (s, 1 H) 10.27 (s, 1 H)

5. Synthesis of 3-(3,3-dichloroallyl)-1-[6-(difluoromethyl)-5-methyl-3-pyrid yl]-3-methyl-4H-iso- quinoline

The solution of 5-[3-(3,3-dichloroallyl)-3-methyl-4H-isoquinolin-1 -yl]-3-methyl-pyridine-2-carbal- dehyde (0,5 g, 1 ,34 mmol) in DCM (40 mL) was added DAST (1 ,534 g, 6,7 mmol) dropwise at 0 °C under N2, the solution was stirred for 1 h at 0°C. The reaction mixture was quenched with aq. NaHCC>3 (60 mL) and extracted with DCM (30 mL), dried over Na2S0 ₄ and concentrated, the residue was purified by Pre-TLC (PE:EtOAc=3:1 ) to give tittle compound (180 mg, 34%) as col- orless oil.

¹ H-NMR (CDCI3, δ in ppm): 1.24 (s, 3 H) 2.46 - 2.57 (m, 2 H) 2.59 (s, 3 H) 2.76 - 2.95 (m, 2 H) 6.07 (t, J=7.59 Hz, 1 H), 6.61 - 6.90 (m, 1 H) 7.17 (d, J=8.03 Hz, 1 H) 7.25 (br. s., 1 H) 7.29 (s, 1 H) 7.41 - 7.46 (m, 1 H) 7.83 (s, 1 H) 8.61 (s, 1 H)

^* HPLC-MS: Rt = 1 ,097 min; M ⁺ +H = 394,9

Example 3) Synthesis of 1 -(5,6-dimethyl-3-pyridyl)spiro[4H-isoquinoline-3,1 -cydopentane] (I-8)

1 ,5 g of trifluoromethane sulfonic acid was added dropwise to a mixture of 0,33 g (2,5 mmol)

5.6- dimethylpyridine-3-carbonitrile and 0,49 g (2,8 mmol) 2— phenylcyclohexanol in 15 mL di- chloroethane at 0 - 5°C. After 12 h at room temperature the reaction mixture was poured onto sodium carbonate solution, the organic layer was separated and the aqueous layer was ex- traded with dichloromethane. The combined organic extracts were extracted with sodium hydrogen carbonate and water, evaporated and the residue was purified via silica gel column chromatography with heptane/ethyl acetate mixtures to yield 0,17 g (24 %) of the title compound as a light yellow oil.

H-NMR (CDCIs, δ in ppm): 8,5 (s, 1 H); 7,6 (s, 1 H); 7,3 (d, 1 H); 7,2-7,1 (m, 2H); 2,8 (s, 2H); 2,6 (s, 3H);2,3 (s, 3H); 1 ,9 (br t, 2H), 1 ,8 (t, 2H); 1 ,6 (m, 4H)

^* HPLC-MS: Rt = 0,746 min; M ⁺ +H = 291 ,2

With due modification of the starting compounds, the procedures shown in the synthesis examples below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.

Table I:

Table I:

0,83 min;

I-22 H H CHs # CHF ₂ CHs 0 - M ⁺ +H=345

0,861 min;

I-23 H H CHs CHF ₂ CHs 0 - M ⁺ +H=313

^O H 0,74 min;

I-24 H H CHs # CHF ₂ CHs 0 - M ⁺ +H=317

1 ,104 min;

I-25 H H CHs CHF ₂ CHs 0 -

# M ⁺ +H=312,1

1 ,042 min;

I-26 H H CHs CHF ₂ CHs 0 -

# M ⁺ +H=31 1

0,984 min;

I-27 H H CHs # CHF ₂ CHs 1 6-F

M ⁺ +H=367,1

1 ,099 min;

I-28 H H CHs ft CHF ₂ CHs 1 6-F

# M ⁺ +H=330

/—F 0,910 min;

I-29 H H CHs # CHF ₂ CHs 0 - M ⁺ +H=319,1

0,961 min;

I-30 H H CHs # CHF ₂ CHs 1 6-F

M ⁺ +H=337,1

CI

CHs 0,921 min;

1-31 H H CHs CHs 0 -

# M ⁺ +H=395

HPLC-MS: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (5 gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1.5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode). II. Biological trials

Microtest

The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide. Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.

In this test, the samples which had been treated with 31 ppm of the active substance from examples I-2, I-3, I-5, I-6, I-7, I-9, 1-10, 1-1 1 , 1-13, 1-14, 1-15, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I- 24 and I-29 respectively, showed up to at most 9 % growth of the pathogen. Example 2 - Activity against Fusarium culmorum in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

In this test, the samples which had been treated with 31 ppm of the active substance from examples I-3, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-15, 1-18, 1-21 and I-23 respectively, showed up to at most 16 % growth of the pathogen

Example 3 - Activity against rice blast Pyricularia oryzae in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.

In this test, the samples which had been treated with 31 ppm of the active substance from 1-1 , I- 3, I-4, I-5, I-7, I-8, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14 ,1-15, 1-16, 1-17, 1-18, 1-19, I-20, 1-21 , I-22, I-23, I- 24 and I-29 respectively, showed up to at most 13 % growth of the pathogen.

Example 4 - Activity against leaf blotch on wheat caused by Septoria tritici The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici Ίη a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.

In this test, the samples which had been treated with 31 ppm of the active substance from examples I-3, I-5, I-6, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-18, 1-19, I-20, 1-21 , I-23 and I-29 respectively, showed up to at most 13 % growth of the pathogen. The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds.

Green House

The spray solutions were prepared in several steps:

The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) sol- vent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml. Water was then added to total volume of 100 ml.

This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.

Example 1 - Preventative fungicidal control of Botrytis cinerea on leaves of green pepper

Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24· C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the samples which had been treated with 250 ppm of the active substance from examples 1-14, 1-15, 1-19, I-20, 1-21 , I-22, I-23, I-25, I-26, I-27, I-28 and I-30 respectively, showed up to at most 1 1 % growth of the pathogen whereas the untreated plants were 80% infected. Example 2 - Long lasting control of Botrytis cinerea on leaves of green pepper

Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The plants were then cultivated in the greenhouse for 7 days and then inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24· C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

In this test, the samples which had been treated with 250 ppm of the active substance from examples I-3, I-5, I-9, 1-10, 1-1 1 , 1-12, 1-13, 1-14, 1-15, 1-19, I-20, 1-21 , I-26 and I-27 respectively, showed up to at most 13 % growth of the pathogen whereas the untreated plants were 80% infected.

III. Comparative Examples Microtest

The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.

Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation. Growth (%) at

Compound Structure

8 ppm

State of the art 36

I-3 1

1-1 1 0

Example 2 - Activity against Fusanum culmorum in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Fusarium culmorum in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

Growth (%)

Compound Structure

at 31 ppm

State oft he art 58

Example 3 - Activity against rice blast Pynculana oryzae in the microtiterplate test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.

Growth (%) at 0.5

Compound Structure

PPm

State of the art 60

I-3 1

Example 4 - Activity against leaf blotch on wheat caused by Septoria tritid

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici ^' m a DOB medium solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 9 days after the inoculation.

Green House

The spray solutions were prepared in several steps: The stock solution were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) sol- vent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml.

Water was then added to total volume of 100 ml.

This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.

Example 1 - Long lasting control of Botrytis cinema on leaves of green pepper

Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The plants were then cultivated in the greenhouse for 7 days and then inoculated with an aqueous biomalt solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24°C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.