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Title:
NOVEL FUNGICIDAL PYRAZOLE DERIVATIVES
Document Type and Number:
WIPO Patent Application WO/2016/026830
Kind Code:
A1
Abstract:
The invention relates to novel pyrazole derivatives of formula (I), to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for controlling harmful microorganisms in crop protection and in the protection of materials. (I) wherein R is H, CH3, F, CI or Br; X is O or NH; Y is C=O, CHRa or S(O)p, with Ra is H or CH3, and p is 1 or 2; Q1 is an optionally substituted 5- to 7-membered carbocyclic ring or 5- to 7-membered heterocyclic ring; and Q2 is an optionally substituted 5- to 7-membered carbocyclic ring, 5- to 7-membered heterocyclic ring or linear or branched alkyl.

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Inventors:
TELSER JOACHIM (DE)
CRISTAU PIERRE (FR)
RINOLFI PHILIPPE (FR)
Application Number:
PCT/EP2015/068893
Publication Date:
February 25, 2016
Filing Date:
August 18, 2015
Export Citation:
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Assignee:
BAYER CROPSCIENCE AG (DE)
International Classes:
C07D231/20; A01N43/56; C07D231/38; C07D231/40; C07D231/42; C07D409/12; C07F7/08
Domestic Patent References:
WO2004083193A12004-09-30
WO2013126283A12013-08-29
WO2010101973A12010-09-10
Foreign References:
EP1852428A12007-11-07
JP2005104968A2005-04-21
JPS6425762A1989-01-27
Other References:
G. WINTERS ET AL: "Synthesis and analgesic activity of new tricyclic pyrazolo[3,4-b]pyridines", FARMACO, EDIZIONE SCIENTIFICA, vol. 40, no. 11, 1985, pages 845 - 853, XP001057121, ISSN: 0430-0920
Attorney, Agent or Firm:
BIP PATENTS (Alfred-Nobel-Str. 10, Monheim am Rhein, DE)
Download PDF:
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Claims:
Claims

1. Compound of formula (I)

(I)

;rs and/or salts thereof, wherein

R is H, CH3, F, CI or Br, X is O or NH, Y is a structure element selected from the group consisting of (C=0), CHRa and S(0)p, wherein Ra is H or CH3, and wherein p is 1 or 2, is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents RQ1; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(=0) and C(=S), and, if present, the sulfur atom ring members are independently selected from

S, S(O), S(0)¾ wherein the heterocyclic ring is optionally substituted with up to 5 substituents RQ1 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present, wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Cehaloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, alkyl, -NR1NR2N and optionally substituted phenyl, is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents

RQ2; or a linear or branched alkyl, optionally substituted with one or more substituents RQ2; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein optionally up to 3 carbon ring members are independently selected from C(=0) and C(=S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(0)¾ wherein the heterocyclic ring is optionally substituted with up to 5 substituents RQ2 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present, wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Cehaloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, alkyl, -NR1NR2N and optionally substituted phenyl, wherein each RN is independently selected from the group consisting of cyano, Ci-Ce alkyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-Ce alkoxy, C2-C6 alkoxyalkyl, d-Ce alkylcarbonyl, d-Ce alkoxycarbonyl, d-Ce alkylaminoalkyl and C3-C6 dialkylaminoalkyl, Ci-Ce arninoalkyl, benzyl, and S02RS, wherein each Rc is independently selected from the group consisting of H and C1-C4 alkyl, wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloal- kyl, wherein each Rs is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, Ci- C4 alkyl, C1-C4 haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy,

(Ci-C4)-alkoxy-(Ci-C4)-alkoxy, (C1-C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

Compound of formula (I) according to claim 1, tautomers and/or salts thereof, wherein R is H, CH3, F, CI or Br, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q1 is a 5- to 7-membered fully saturated, a partially unsaturated 5- or 6-membered carbocy- clic ring, or a phenyl ring, optionally substituted with up to 5 substituents RQ1; or a 5- to 7-membered fully saturated or a fully unsaturated 5- or 6-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein the heterocyclic ring is optionally substituted with up to 3 substituents RQ1 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, d-Ce alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH=NO-Ci-C4 alkyl, -NR1NR2N and optionally substituted phenyl, is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents RQ2; or a linear or branched alkyl with a total of 1 to 12 carbon atoms, optionally substituted with one or more substituents RQ2; or is a fully unsaturated or a fully saturated 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is optionally substituted with up to 5 (i.e. 0, 1, 2, 3, 4 or 5) substituents RQ2 on carbon atom heterocyclic ring members and optionally substituted with substituents RN on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Cehaloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH=NO-Ci-C4 alkyl, -NR1NR2N and optionally substituted phenyl, wherein each RN is independently selected from the group consisting of cyano, Ci-Ce alkyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-Ce alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl and C3-C6 dialkylaminoalkyl, Ci-Ce aminoalkyl, benzyl, and S02RS, wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloal- kyl, wherein each Rs is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, Ci- C4 alkyl, C1-C4 haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4)-alkoxy-(Ci-C4)-alkoxy, (C1-C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

Compound of formula (I) according to claim 1 or 2, tautomers and/or salts thereof, wherein R is H, CH3, F, CI or Br, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2,

Q1 is a ring selected from the group consisting of phenyl and 5- or 6-membered heteroaro- matic rings, wherein Q1 is optionally substituted with up to 5 substituents RQ1; wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH=NO-Ci-C4 alkyl, -NR1NR2N and optionally substituted phenyl, is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic or heterocyclic ring, preferably a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents RQ2; or a linear or branched alkyl with a total of 1 to 8 carbon atoms, optionally substituted with up to 12 substituents RQ2; wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Cehaloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, d-Ce alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcyclo- alkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 alkylcarbonyloxy, C1-C4 alka- noylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C4-alkyl)silyl, SCF3, SF5, SCN, isonitrile, CH=NO-Ci-C4 alkyl, and -NR1NR2N, wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloal- kyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, Ci- C4 alkyl, C1-C4 haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4)-alkoxy-(Ci-C4)-alkoxy, (C1-C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

4. Compound of formula (I) according to any one of claims 1 to 3, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2,

Q1 is a phenyl ring, optionally substituted with up to 5 substituents RQ1; wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Cehaloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloal- koxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, and -NR1NR2N, is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents RQ2; wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloal- koxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, tri(Ci-C4- alkyl)silyl, SF5, SCN, isonitrile, and -NR1NR2N, wherein R1N and R2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl.

5. Compound of formula (I) according to any one of claims 1 to 4, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q1 is a phenyl ring, optionally substituted with up to 5 substituents RQ1; wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloal- koxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, and -NR1NR2N, wherein R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents RQ2; wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3- C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy and tri(Ci-C4- alkyl)silyl.

6. Compound of formula (I) according to any one of claims 1 to 5, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q1 is a phenyl ring, optionally substituted with up to 5 substituents RQ1; wherein each RQ1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halo- cycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloal- koxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF5, SCN, isonitrile, and -NR1NR2N, wherein

R1N and R2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, provided that at least one of the substituents RQ1 is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy and C3-C7 alkynyloxy,

Q2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents RQ2, wherein each RQ2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, C1-C6 haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3- C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy.

7. Compound of formula (I) according to any one of claims 1 to 6, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q1 is a phenyl ring substituted with one or more substituents RQ1 selected from the group consisting of F, CI, Br, I, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy and C3-C7 alkynyloxy,

Q2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents RQ2; wherein each RQ2 is independently selected from the group consisting of F, CI, Br, I, cyano, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C7 alkynyloxy.

8. Compound of formula (I) according to any one of claims 1 to 7, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2, is a phenyl ring substituted with one or more substituents RQ1 selected from the group consisting of F, CI, Br, I, cyano, nitro, amino, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C6 al- kynyloxy, is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents RQ2, wherein each RQ2 is independently selected from the group consisting of F, CI, Br, I, cy- ano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C6 alkynyloxy.

9. Compound of formula (I) according to any one of claims 1 to 8, tautomers and/or salts thereof, wherein

R is CH3 or CI, X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q1 is a phenyl ring substituted with one or more substituents RQ1 selected from the group consisting of F, CI, Br, I, CN, CH3, CC13, CHF2, CF3, CH2CF3, OCH3, OCF3, propargyloxy and allyloxy,

Q2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclo- hexyl, optionally substituted with up to 5 independently selected substituents RQ2; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents RQ2, wherein each RQ2 is independently selected from the group consisting of F, CI, Br, I, CN, CH3, CCI3, CHF2, CF3, CH2CF3, OCH3, OCF3, propargyloxy and allyloxy.

10. Compound of formula (I) according to any one of claims 1 to 9, tautomers and/or salts thereof, wherein the following applies - when X is O, then Y is CH2;

- when X is NH, then Y is (C=0) or S02.

11. Composition comprising

(a) a fungicidally effective amount of a compound as defined in any one of claims 1 to 10, and one or more further constituents selected from the group consisting of groups (b) and (c):

(b) agrochemically acceptable adjuvants, preferably selected from the group consisting of surfactants, liquid diluents and solid diluents, and

(c) other pesticidally active ingredients.

12. Method for controlling one or more plant diseases caused by fungal plant pathogens, comprising the steps of

(i) providing a compound of the formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 11, and

(ii) applying to the plant, to a portion of the plant or to plant seeds a fungicidally effective amount the compound provided in step (i).

13. Use of a compound of the formula (I) as defined in any one of claims 1 to 10 or a composition as defined in claim 11 for controlling fungi, preferably for controlling fungi in plants or plant seeds.

Method for producing a compound of formula (I) as defined in any one of claims 1 to 10, characterized by the following steps:

(i) providing a compound of the formula (Z-a)

(Z-a) wherein R, X, and Q1 each have the meaning as defined in any one of claims 1 to 10,

(ii) providing a compound of the formula (Z-b)

Q2-Y

LG (Z-b) wherein Q2 has the meaning as defined in any one of claims 1 to 10, and wherein LG is a leaving group,

(iii) reacting compounds (Z-a) and (Z-b), thereby obtaining a compound of formula (I) as defined in any one of claims 1 to 10.
Description:
- -

NOVEL FUNGICIDAL PYRAZOLE DERIVATIVES

The present invention relates to novel pyrazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for controlling harmful microorganisms in crop protection and in the protection of materials. The control of harmful microorganisms in crop protection is very important for achieving high crop efficiency. Plant disease damage to ornamental, vegetable, field, cereal or fruit crops can cause significant reduction in productivity. There are many active ingredients available today for controlling harmful microorganisms in crop protection, but there continues to be a need for new active ingredients for controlling harmful microorganisms. It is already known that certain pyrazole derivatives have fungicidal properties (e.g. WO 2009/127612, WO 2009/137538, WO 2010/101973, WO 2012/023143, WO 2012/024586, WO 2012/030922, WO 2012/031061, WO 2013/116251, WO 2013/126283, WO 2013/192126, EP 2 604 114, WO 2014/130241, WO 2014/130409, US 2014/0288074 and WO 2015/026646).

Since the ecological and economic demands made on modern active ingredients, for example fungicides, are increasing constantly, for example with respect to activity spectrum, toxicity, selectivity, application rate, formation of residues and favorable manufacture, and there can also be problems, for example, with resistances, there is a constant need to develop novel fungicidal compositions which have advantages over the known compositions at least in some areas.

The present invention provides novel pyrazole derivatives of the formula (I)

(I) tautomers and/or salts thereof, wherein

R is H, CH 3 , F, CI or Br,

X is O or NH, is a structure element selected from the group consisting of (C=0), CHR a and S(0) p , wherein R' H or CH3, and wherein p is 1 or 2, (i.e. X and Y together are linking Q 2 to the pyrazole ring), is a 5- to 7-membered carbocyclic ring, optionally substituted with up to 5 independently selected substituents R Q1 (i.e. 0, 1, 2, 3, 4 or 5 substituents R Q1 in case Q 1 is a 6-membered carbocyclic ring, and 0, 1, 2, 3 or 4 substituents R Q1 in case Q 1 is a 5-membered carbocyclic ring); or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 (i.e. 1, 2 or 3) heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom (i.e. no or one oxygen atom), up to 1 S atom (i.e. no or one sulfur atom), and up to 3 (i.e. 0, 1, 2 or 3) N atoms, wherein optionally up to 3 (i.e. 0, 1, 2 or 3) carbon ring members are independently selected from C(=0) and C(=S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(0) ¾ wherein the heterocyclic ring is optionally substituted with up to 5 (i.e. 0, 1, 2, 3, 4 or 5) substituents R Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R N on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, alkyl, -NR 1N R 2N and optionally substituted phenyl, is a 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R Q2 (i.e. 0, 1, 2, 3, 4 or 5 substituents R Q2 in case Q 2 is a 6-membered carbocyclic ring, and 0, 1, 2, 3 or 4 substituents R Q2 in case Q 2 is a 5-membered carbocyclic ring); or a linear or branched alkyl, optionally substituted with one or more substituents R Q2 ; or a 5- to 7-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 (i.e. 1, 2 or 3) heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom (i.e. no or one oxygen atom), up to 1 S atom (i.e. no or one sulfur atom), and up to 3 (i.e. 0, 1, 2 or 3) N atoms, wherein optionally up to 3 (i.e. 0, 1, 2 or 3) carbon ring members are independently selected from C(=0) and C(=S), and, if present, the sulfur atom ring members are independently selected from S, S(O), S(0)2, wherein the heterocyclic ring is optionally substituted with up to 5 (i.e. 0, 1, 2, 3, 4 or 5) substituents R Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R N on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, alkyl, -NR 1N R 2N and optionally substituted phenyl, wherein each R N is independently selected from the group consisting of cyano, Ci-Ce alkyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-Ce alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl and C3-C6 dialkylaminoalkyl, Ci-Ce aminoalkyl, benzyl, and S02R S , wherein each R c is independently selected from the group consisting of H and C1-C4 alkyl, wherein R 1N and R 2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, wherein each R s is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 (i.e. 0, 1, 2, 3, 4 or 5) radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (Ci-C 4 )-alkoxy-(Ci-C 4 )-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (C1-C4)- alkoxy-(Ci-C4)-alkoxy, (C1-C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

If in the context of the present invention reference is made to a compound of the formula (I), reference is also made to the tautomers and/or salts thereof. In the formula (I) and in all subsequent formulae, chemical radicals or substituents are referred to by names which are collective terms for the enumeration of individual group members or specifically refer to individual chemical radicals. In general, terms are used which are familiar to the person skilled in the art and/or in particular have the meanings illustrated below. A hydrocarbon radical is an aliphatic, cycloaliphatic or aromatic monocyclic or, in the case of an optionally substituted hydrocarbon radical, also a bicyclic or polycyclic organic radical based on the elements carbon and hydrogen, including, for example, the radicals alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, naphthyl, indanyl, indenyl, etc.; this applies correspondingly to hydrocarbon radicals in composite meanings, such as hydrocarbonoxy radicals or other hydrocarbon radicals attached via heteroatom groups.

The hydrocarbon radicals, also in the special radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio, and also the corresponding unsaturated and/or substituted radicals may in each case be straight- chain or branched in the carbon skeleton.

The expression "C1-C4 alkyl" is a brief notation for alkyl having from 1 to 4 carbon atoms, i.e. encompasses the methyl, ethyl, 1 -propyl, 2-propyl, 1 -butyl, 2-butyl, 2-methylpropyl or tert-butyl radicals. General alkyl radicals with a larger specified range of carbon atoms, e.g. "C1-C6 alkyl", correspondingly also encompass straight-chain or branched alkyl radicals with a greater number of carbon atoms, i.e. according to the example also the alkyl radicals having 5 and 6 carbon atoms.

Alkyl radicals, including in the combined definitions such as alkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls such as n-hexyl, i-hexyl and 1,3- dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1 ,4-dimethylpentyl; alkenyl and alkynyl radicals are defined as the possible unsaturated radicals corresponding to the alkyl radicals; alkenyl is, for example, vinyl, allyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl group, preferably allyl, l-methylprop-2-en-l-yl, 2-methylprop-2-en-l-yl, but-2-en-l-yl, but-3-en- 1 -yl, 1 -methylbut-3 -en- 1 -yl or 1 -methylbut-2-en- 1 -yl.

Cycloalkyl is a carbocyclic saturated ring system, for example cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. In the case of substituted cycloalkyl, cyclic systems with substituents are included, where the substituents may also be bonded by a double bond on the cycloalkyl radical.

Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully substituted by identical or different halogen atoms, preferably from the group consisting of fluorine, chlorine, bromine and iodine, in particular from the group consisting of fluorine, chlorine and bromine, very particularly from the group consisting of fluorine and chlorine, for example monohaloalkyl, perhaloalkyl, CF3, CHF2, CH2F, CF3CF2, CH2FCHCI, CCI3, CHCb, CH2CH2CI; haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF3CF2O, OCH2CF3 and OCH2CH2CI; this applies correspondingly to haloalkenyl and other halogen-substituted radicals such as, for example, halocycloalkyl.

In the context of the present invention, "propargyl" means prop-2-yn-l-yl, "allyl" means prop-2-en-l-yl, "propargyloxy" means prop-2-yn-l-yloxy, and "allyloxy" means prop-2-en-l-yloxy. A heterocyclic radical (heterocyclyl) comprises at least one heterocyclic ring (=carbocyclic ring in which at least one carbon atom is replaced by a heteroatom (from the group consisting of N, O, S), which is saturated, unsaturated or heteroaromatic and may be unsubstituted or substituted, where the point of attachment is located at a ring atom.

Unless defined otherwise it preferably contains one or more, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring from the group consisting of N, O, and S; it is preferably an aliphatic heterocyclyl radical having 5 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms. The heterocyclic radical may, for example, be a heteroaromatic radical or ring (heteroaryl).

It is preferably a radical of a five- or six-membered heteroaromatic ring, such as pyridyl, pyrrolyl, thienyl or furyl. it is furthermore preferably a radical of a corresponding heteroaromatic ring having 2, 3 or 4 heteroatoms, for example pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl or triazolyl.

Here, preference is given to a radical of a heteroaromatic five- or six-membered ring having 1 to 3 heteroatoms, such as, for example, 1,2,3 -triazolyl, 1 ,2,4-triazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4- oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3 -thiadiazolyl, 1 ,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1 ,2,5-thiadiazolyl, 1,2,3 -triazinyl, 1 ,2,4-triazinyl, 1,3,5-triazinyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyrazolyl, imidazolyl.

More preference is given here to heteroaromatic radicals of five-membered heterocycles having 3 nitrogen atoms, such as 1,2,3-triazol-l-yl, l,2,3-triazol-4-yl, l,2,3-triazol-5-yl, 1,2,5-triazol-l-yl, l,2,5-triazol-3-yl, 1,3,4-triazol-l-yl, l,3,4-triazol-2-yl, l,2,4-triazol-3-yl, l,2,4-triazol-5-yl; more preference is also given here to heteroaromatic radicals of six-membered heterocycles having 3 nitrogen atoms, such as l,3,5-triazin-2-yl, l,2,4-triazin-3-yl, l,2,4-triazin-5-yl, 1 ,2,4-triazin-6-yl, 1,2,3- triazin-4-yl, l,2,3-triazin-5-yl; more preference is also given here to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one oxygen atom, such as l,2,4-oxadiazol-3-yl; l,2,4-oxadiazol-5-yl, 1,3,4-oxadiazol- 2-yl, l,2,3-oxadiazol-4-yl, l,2,3-oxadiazol-5-yl, l,2,5-oxadiazol-3-yl, more preference is also given here to heteroaromatic radicals of five-membered heterocycles having two nitrogen atoms and one sulfur atom, such as l,2,4-thiadiazol-3-yl, l,2,4-thiadiazol-5-yl, l,3,4-thiadiazol-2- yl, l,2,3-thiadiazol-4-yl, l,2,3-thiadiazol-5-yl, l,2,5-thiadiazol-3-yl.

Furthermore preferably, the heterocyclic radical or ring is a partially or fully hydrogenated heterocyclic radical having one heteroatom from the group of N, O and S, for example oxolanyl (= tetrahydrofuryl), oxanyl, pyrrolinyl, pyrrolidyl or piperidyl.

It is also preferably a partially or fully hydrogenated heterocyclic radical having 2 heteroatoms from the group of N, O and S, for example piperazinyl, dioxolanyl, oxazolinyl, isoxazolinyl, oxazolidinyl, isoxazolidinyl and morpholinyl. Suitable substituents for a substituted heterocyclic radical are the substituents specified later on below.

When a structural element is substituted "by one or more radicals" from a list of substituents (radicals) or a generically defined group of substituents (radicals), this in each case includes simultaneous substitution by a plurality of identical and/or structurally different substituents (radicals).

Preferred compounds of formula (I) according to the present invention, tautomers and/or salts thereof, are compounds wherein

R is H, CH 3 , F, CI or Br,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CFh and SO2,

Q 1 is a 5- to 7-membered fully saturated, a partially unsaturated 5- or 6-membered carbocyclic ring, or a phenyl ring, optionally substituted with up to 5 substituents R Q1 ; or a 5- to 7-membered fully saturated or a fully unsaturated 5- or 6-membered heterocyclic ring containing ring members selected from the group consisting of C, N, O and S, and containing up to 3 heteroatom ring members independently selected from the group O, S, and N, wherein the heterocyclic ring contains as heteroatom ring members up to 1 O atom, up to 1 S atom, and up to 3 N atoms, wherein the heterocyclic ring is optionally substituted with up to 3 substituents R Q1 on carbon atom heterocyclic ring members and optionally substituted with substituents R N on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, d-Ce alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, CH=NO-Ci-C 4 alkyl, -NR 1N R 2N and optionally substituted phenyl, is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 12 carbon atoms, optionally substituted with one or more substituents R Q2 ; or is a fully unsaturated or a fully saturated 5- or 6-membered heterocyclic ring, wherein the heterocyclic ring is optionally substituted with up to 5 (i.e. 0, 1, 2, 3, 4 or 5) substituents R Q2 on carbon atom heterocyclic ring members and optionally substituted with substituents R N on nitrogen atom heterocyclic ring members, if present (i.e. if one or more nitrogen atom heterocyclic ring members are present), wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, CH=NO-Ci-C 4 alkyl, -NR 1N R 2N and optionally substituted phenyl, wherein each R N is independently selected from the group consisting of cyano, Ci-Ce alkyl, Ci-Ce haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, Ci-Ce alkoxy, C2-C6 alkoxyalkyl, C2-C6 alkylcarbonyl, C2-C6 alkoxycarbonyl, C2-C6 alkylaminoalkyl and C3-C6 dialkylaminoalkyl, Ci-Ce aminoalkyl, benzyl, and S02R S , wherein R 1N and R 2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, wherein each R s is independently selected from C1-C4 alkyl, C1-C4 haloalkyl, and C3-C6 cycloalkyl, - - wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4)-alkoxy-(Ci-C4)-alkoxy, (Ci- C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

In another preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is H, CH 3 , F, CI or Br,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2,

Q 1 is a ring selected from the group consisting of phenyl and 5- or 6-membered heteroaromatic rings, wherein Q 1 is optionally substituted with up to 5 substituents R Q1 ; wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, CH=NO-Ci-C 4 alkyl, -NR 1N R 2N and optionally substituted phenyl,

Q 2 is a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic or heterocyclic ring, preferably a fully unsaturated or a fully saturated 5- or 6-membered carbocyclic ring, optionally substituted with up to 5 substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 8 carbon atoms, optionally substituted with up to 12 substituents R Q2 ; wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, C3-C6 heterocyclyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkenyloxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halo- cycloalkoxy, C3-C6 heterocyclyloxy, C1-C3 alkylthio, Ci-C3 haloalkylthio, C1-C3 alkylsulfinyl, C1-C3 - - haloalkylsulfinyl, C1-C3 alkylsulfonyl, C1-C3 haloalkylsulfonyl, C1-C2 alkylsulfonyloxy, C1-C2 haloalkylsulfonyloxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C2-C3 alkylcarbonyl, C2-C3 al- kylcarbonyloxy, C1-C4 alkanoylamino, C2-C3 alkylcarbonylamino, (Ci-Ce alkoxy)iminocarbonyl, tri(Ci-C 4 -alkyl)silyl, SCF 3 , SF 5 , SCN, isonitrile, CH=NO-Ci-C 4 alkyl, and -NR 1N R 2N , wherein R 1N and R 2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, wherein each optionally substituted phenyl is independently selected from phenyl substituted with up to 5 radicals selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, (Ci-C4)-alkoxy-(Ci-C4)-alkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, (Ci-C4)-alkoxy-(Ci-C4)-alkoxy, (Ci- C4) alkylthio and nitro, in particular phenyl which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

In a further preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is CH 3 or CI,

X is O or NH, Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q 1 is a phenyl ring, optionally substituted with up to 5 substituents R Q1 ; wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cycloalkylalkyl, C1-C4 alkanoylamino, SF 5 , SCN, isonitrile, and -NR 1N R 2N ,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents R Q2 ;

wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, - -

C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cyclo- alkylalkyl, C1-C4 alkanoylamino, tri(Ci-C 4 -alkyl)silyl, SF 5 , SCN, isonitrile, and -NR 1N R 2N , wherein R 1N and R 2N each are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl.

In a more preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is CH 3 or CI,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q 1 is a phenyl ring, optionally substituted with up to 5 substituents R Q1 ; wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cyclo- alkylalkyl, C1-C4 alkanoylamino, SF 5 , SCN, isonitrile, and -NR 1N R 2N , wherein R 1N and R 2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents R Q2 ; wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy and tri(Ci-C4-alkyl)silyl.

In a more preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2, Q 1 is a phenyl ring, optionally substituted with up to 5 substituents R Q1 ; wherein each R Q1 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, formyl, Ci-Ce alkyl, Ci-Ce haloalkyl, C3-C6 cycloalkyl, C3-C7 halocycloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkenyl, C3-C7 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, C3-C7 alkynyloxy, C3-C7 cycloalkoxy, C3-C6 halocycloalkoxy, C4-C7 alkylcycloalkyl, C4-C6 cyclo- alkylalkyl, C1-C4 alkanoylamino, SF 5 , SCN, isonitrile, and -NR 1N R 2N , wherein

R 1N and R 2N are independently selected from C1-C4 alkyl and C3-C6 cycloalkyl, provided that at least one of the substituents R Q1 is selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy and C3-C7 alkynyloxy,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 8 substituents R Q2 , wherein each R Q2 is independently selected from the group consisting of halogen, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy, and C3-C7 alkynyloxy.

In an even more preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q 1 is a phenyl ring substituted with one or more, preferably one, two or three, substituents R Q1 selected from the group consisting of F, CI, Br, I, cyano, nitro, amino, hydroxy, Ci-Ce alkyl, Ci-Ce haloalkyl, Ci-Ce alkoxy, Ci-Ce haloalkoxy, C3-C4 alkenylalkoxy, C2-C6 alkynyl, C3-C7 alkynylalkoxy and C3-

C7 alkynyloxy, is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents R Q2 ; wherein each R Q2 is independently selected from the group consisting of F, CI, Br, I, cyano, hydroxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C7 alkynyloxy.

In an even more preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2,

Q 1 is a phenyl ring substituted with one or more, preferably one, two or three, substituents R Q1 selected from the group consisting of F, CI, Br, I, cyano, nitro, amino, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C6 alkynyloxy,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents R Q2 , wherein each R Q2 is independently selected from the group consisting of F, CI, Br, I, cyano, hydroxy, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C3-C4 alkenylalkoxy, C3-C7 alkynylalkoxy and C3-C6 alkynyloxy.

In a particularly preferred embodiment of the present invention, the invention relates to a compound of formula (I) as defined above, tautomers and/or salts thereof, wherein

R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2, Q 1 is a phenyl ring substituted with one or more, preferably one, two or three, substituents R Q1 selected from the group consisting of F, CI, Br, I, CN, CH 3 , CC1 3 , CHF 2 , CF 3 , CH2CF3, OCH 3 , OCF 3 , pro- pargyloxy and allyloxy,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 6 carbon atoms, optionally substituted with up to 4 substituents R Q2 , wherein each R Q2 is independently selected from the group consisting of F, CI, Br, I, CN, CH3, CCI3, CHF 2 , CF 3 , CH2CF3, OCH3, OCF3, propargyloxy and allyloxy.

Particularly preferred according to the present invention are compounds of formula (I), tautomers and/or salts thereof, wherein

R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), CH2 and SO2,

Q 1 is a phenyl ring substituted with two or more, preferably two or three, substituents R Q1 selected from the group consisting of F, CI, Br, I, CN, CH 3 , CC1 3 , CHF 2 , CF 3 , CH2CF3, OCH 3 , OCF 3 , propargyloxy and allyloxy,

Q 2 is a ring selected from the group consisting of phenyl, cyclopropyl, cyclopentyl and cyclohexyl, optionally substituted with up to 5 independently selected substituents R Q2 ; or a linear or branched alkyl with a total of 1 to 4 carbon atoms, optionally substituted with 0, 1 or 2 substituents R Q2 ; wherein each R Q2 is independently selected from the group consisting of F, CI, Br, I, CN, CH3, CCI3, CHF 2 , CF 3 , CH2CF3, OCH3, OCF3, propargyloxy and allyloxy.

In view of their remarkable and strong fungicidal activity, particularly preferred according to the present invention are compounds of formula (I), tautomers and/or salts thereof, wherein the following applies:

- when X is O, then Y is CH 2 ;

- when X is NH, then Y is (C=0) or S0 2 .

Particularly preferred compounds of the formula (I) according to the invention are those, wherein: - -

Q is selected from the group consisting of cyclopropyl, cyclopentyl, tert-butyl, isopropyl, methyl, ethyl, 2-(trimethylsilyl)ethyl, 2-methoxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 3 -fluorophenyl, 3- chlorophenyl, 4-fluorophenyl, 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6- dichlorophenyl, 2-chloro-3 -fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2-chloro-6- fluorophenyl, 3-chloro-2-fluorophenyl, 3-chloro-4-fluorophenyl, 3-chloro-5-fluorophenyl, 3-chloro-6- fluorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3 -fluorophenyl, 2-bromo-4-fluorophenyl, 2-bromo-5- fluorophenyl, 4-fluoro-2-methylphenyl, 5-fluoro-2-methylphenyl, 2,4,6-trifluorophenyl, 3- (trifluoromethyl)phenyl, and 5-chloro-2-thienyl.

Particularly preferred compounds of the formula (I) according to the invention are those, wherein:

Q 1 is selected from the group consisting of 2-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 4- allyloxy-2,6-difluorophenyl, 2,6-difluoro-4-propargyloxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,4,6- trifluorophenyl, 3,5-dimethoxyphenyl, 4-cyano-2,6-difluorophenyl, 4-bromo-2,6-difluorophenyl, and 2,6- difluoro-4-methylphenyl.

More particularly preferred compounds of the formula (I) according to the invention are those, wherein: R is CH 3 or CI, preferably CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q 1 is selected from the group consisting of 2-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 4- allyloxy-2,6-difluorophenyl, 2,6-difluoro-4-propargyloxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,4,6-trifluorophenyl, 3,5-dimethoxyphenyl, 4-cyano-2,6-difluorophenyl, 4-bromo-2,6- difluorophenyl, and 2,6-difluoro-4-methylphenyl,

and

Q 2 is selected from the group consisting of cyclopropyl, cyclopentyl, tert-butyl, isopropyl, methyl, ethyl, 2-(trimethylsilyl)ethyl, 2-methoxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 3 -fluorophenyl, 3- chlorophenyl, 4-fluorophenyl, 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5- difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,5- dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-3 -fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5- fluorophenyl, 2-chloro-6-fluorophenyl, 3-chloro-2-fluorophenyl, 3-chloro-4-fluorophenyl, 3-chloro- 5-fluorophenyl, 3-chloro-6-fluorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3 -fluorophenyl, 2- bromo-4-fluorophenyl, 2-bromo-5-fluorophenyl, 4-fluoro-2-methylphenyl, 5-fluoro-2- methylphenyl, 2,4,6-trifluorophenyl, 3-(trifluoromethyl)phenyl, and 5-chloro-2-thienyl, wherein the following applies:

- when X is O, then Y is CH 2 ;

- when X is NH, then Y is (C=0) or S0 2 . c

Preferred compounds of formula (I) according to the present invention are listed in the following table.

Entry No. X Y R Q 1 Q 2

1 NH CO CH 3 2-chloro-4-fluorophenyl cyclopentyl

2 NH CO CH 3 2-chloro-4-fluorophenyl tert-butyl

3 NH CO CH 3 2-chloro-4-fluorophenyl isopropyl

4 NH CO CH 3 2-chloro-4-fluorophenyl 2-methoxyphenyl

5 NH CO CH 3 2-chloro-4-fluorophenyl cyclopropyl

6 NH CO CH 3 2-chloro-4-fluorophenyl 5-chloro-2-thienyl

7 NH CO CH 3 2-chloro-4-fluorophenyl 2,4-difluorophenyl

8 NH CO CH 3 2-chloro-4-fluorophenyl methyl

9 NH CO CH 3 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

10 NH CO CH 3 2-chloro-4-fluorophenyl 2,6-difluorophenyl

11 NH CO CH 3 2-chloro-4-fluorophenyl 2,4-dichlorophenyl

12 NH CO CH 3 2-chloro-4-fluorophenyl 2-(trimethylsilyl)ethyl

13 NH CO CH 3 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

14 NH CO CH 3 2-chloro-4-fluorophenyl 3 -(trifluoromethyl)phenyl

15 NH so 2 CH 3 4-chloro-2-fluorophenyl ethyl

16 NH so 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

17 O CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-5-fluorophenyl

18 O CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

19 0 CH 2 CH 3 2-chloro-4-fluorophenyl 4-fluorophenyl

20 0 CH 2 CH 3 2-chloro-4-fluorophenyl 4-chlorophenyl

21 0 CH 2 CH 3 2-chloro-4-fluorophenyl 3-chlorophenyl

22 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,4,6-trifluorophenyl

23 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,6-dichlorophenyl

24 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,6-difluorophenyl

25 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

26 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,4-dichlorophenyl

27 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-chlorophenyl

28 0 CH 2 CH 3 2-chloro-4-fluorophenyl 3 -fluorophenyl

29 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-fluorophenyl

30 0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,4-difluorophenyl

31 NH CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-5-fluorophenyl

32 NH CH 2 CH 3 2-chloro-4-fluorophenyl 4-fluorophenyl - -

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3 -fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 4-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3-chlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 4-chlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,3 -difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,4-difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,5-difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,6-difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3 ,4-difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3,5-difluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,4-dichlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,6-dichlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,4,6-trifluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-3 -fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-5-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3 -chloro-2-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3 -chloro-4-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3-chloro-5-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 3 -chloro-6-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 4-chloro-2-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 4-chloro-3 -fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2,5-dichlorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-bromo-4-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 2-bromo-5-fluorophenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 4-fluoro-2-methylphenyl

0 CH 2 CH 3 4-chloro-2-fluorophenyl 5-fluoro-2-methylphenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,3 -difluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,5-difluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3 ,4-difluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3,5-difluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-3 -fluorophenyl - 7 -

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3 -chloro-2-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3 -chloro-4-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3-chloro-5-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 3 -chloro-6-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 4-chloro-2-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 4-chloro-3 -fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2,5-dichlorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-bromo-4-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 2-bromo-5-fluorophenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 4-fluoro-2-methylphenyl

0 CH 2 CH 3 2-chloro-4-fluorophenyl 5-fluoro-2-methylphenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3 -fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 4-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chlorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3-chlorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 4-chlorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,3 -difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,4-difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,5-difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,6-difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3 ,4-difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3,5-difluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,4-dichlorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,6-dichlorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,4,6-trifluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-5-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3 -chloro-2-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3-chloro-5-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 4-chloro-2-fluorophenyl - -

105 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

106 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2,5-dichlorophenyl

107 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

108 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-bromo-4-fluorophenyl

109 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-bromo-5-fluorophenyl

110 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 4-fluoro-2-methylphenyl

111 0 CH 2 CH 3 4-allyloxy-2,6-difluorophenyl 5-fluoro-2-methylphenyl

2,6-difluoro-4-

112 0 CH 2 CH 3 2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

113 0 CH 2 CH 3 3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

114 0 CH 2 CH 3 4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

115 0 CH 2 CH 3 2-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

116 0 CH 2 CH 3 3-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

117 0 CH 2 CH 3 4-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

118 0 CH 2 CH 3 2,3 -difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

119 0 CH 2 CH 3 2,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

120 0 CH 2 CH 3 2,5-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

121 0 CH 2 CH 3 2,6-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

122 0 CH 2 CH 3 3 ,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

123 0 CH 2 CH 3 3,5-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

124 0 CH 2 CH 3 2,4-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

125 0 CH 2 CH 3 2,6-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

126 0 CH 2 CH 3 2,4,6-trifluorophenyl propargyloxyphenyl - -

2,6-difluoro-4-

127 0 CH 2 CH 3 2-chloro-3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

128 0 CH 2 CH 3 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

129 0 CH 2 CH 3 2-chloro-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

130 0 CH 2 CH 3 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

131 0 CH 2 CH 3 3 -chloro-2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

132 0 CH 2 CH 3 3 -chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

133 0 CH 2 CH 3 3-chloro-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

134 0 CH 2 CH 3 3 -chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

135 0 CH 2 CH 3 4-chloro-2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

136 0 CH 2 CH 3 4-chloro-3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

137 0 CH 2 CH 3 2,5-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

138 0 CH 2 CH 3 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

139 0 CH 2 CH 3 2-bromo-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

140 0 CH 2 CH 3 2-bromo-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

141 0 CH 2 CH 3 4-fluoro-2-methylphenyl propargyloxyphenyl

2,6-difluoro-4-

142 0 CH 2 CH 3 5-fluoro-2-methylphenyl propargyloxyphenyl

2,6-difluoro-4-

143 0 CH 2 CH 3 2-fluorophenyl methoxyphenyl

2,6-difluoro-4-

144 0 CH 2 CH 3 3 -fluorophenyl methoxyphenyl

145 0 CH 2 CH 3 2,6-difluoro-4- 4-fluorophenyl - - methoxyphenyl

2,6-difluoro-4-

146 0 CH 2 CH 3 2-chlorophenyl methoxyphenyl

2,6-difluoro-4-

147 0 CH 2 CH 3 3-chlorophenyl methoxyphenyl

2,6-difluoro-4-

148 0 CH 2 CH 3 4-chlorophenyl methoxyphenyl

2,6-difluoro-4-

149 0 CH 2 CH 3 2,3 -difluorophenyl methoxyphenyl

2,6-difluoro-4-

150 0 CH 2 CH 3 2,4-difluorophenyl methoxyphenyl

2,6-difluoro-4-

151 0 CH 2 CH 3 2,5-difluorophenyl methoxyphenyl

2,6-difluoro-4-

152 0 CH 2 CH 3 2,6-difluorophenyl methoxyphenyl

2,6-difluoro-4-

153 0 CH 2 CH 3 3 ,4-difluorophenyl methoxyphenyl

2,6-difluoro-4-

154 0 CH 2 CH 3 3,5-difluorophenyl methoxyphenyl

2,6-difluoro-4-

155 0 CH 2 CH 3 2,4-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

156 0 CH 2 CH 3 2,6-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

157 0 CH 2 CH 3 2,4,6-trifluorophenyl methoxyphenyl

2,6-difluoro-4-

158 0 CH 2 CH 3 2-chloro-3 -fluorophenyl methoxyphenyl

2,6-difluoro-4-

159 0 CH 2 CH 3 2-chloro-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

160 0 CH 2 CH 3 2-chloro-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

161 0 CH 2 CH 3 2-chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

162 0 CH 2 CH 3 3 -chloro-2-fluorophenyl methoxyphenyl

2,6-difluoro-4-

163 0 CH 2 CH 3 3 -chloro-4-fluorophenyl methoxyphenyl - -

2,6-difluoro-4-

164 0 CH 2 CH 3 3-chloro-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

165 0 CH 2 CH 3 3 -chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

166 0 CH 2 CH 3 4-chloro-2-fluorophenyl methoxyphenyl

2,6-difluoro-4-

167 0 CH 2 CH 3 4-chloro-3 -fluorophenyl methoxyphenyl

2,6-difluoro-4-

168 0 CH 2 CH 3 2,5-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

169 0 CH 2 CH 3 2-chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

170 0 CH 2 CH 3 2-bromo-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

171 0 CH 2 CH 3 2-bromo-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

172 0 CH 2 CH 3 4-fluoro-2-methylphenyl methoxyphenyl

2,6-difluoro-4-

173 0 CH 2 CH 3 5-fluoro-2-methylphenyl methoxyphenyl

174 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-fluorophenyl

175 0 CH 2 CH 3 2,4,6-trifluorophenyl 3 -fluorophenyl

176 0 CH 2 CH 3 2,4,6-trifluorophenyl 4-fluorophenyl

177 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chlorophenyl

178 0 CH 2 CH 3 2,4,6-trifluorophenyl 3-chlorophenyl

179 0 CH 2 CH 3 2,4,6-trifluorophenyl 4-chlorophenyl

180 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,3 -difluorophenyl

181 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,4-difluorophenyl

182 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,5-difluorophenyl

183 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,6-difluorophenyl

184 0 CH 2 CH 3 2,4,6-trifluorophenyl 3 ,4-difluorophenyl

185 0 CH 2 CH 3 2,4,6-trifluorophenyl 3,5-difluorophenyl

186 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,4-dichlorophenyl

187 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,6-dichlorophenyl

188 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,4,6-trifluorophenyl

189 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chloro-3 -fluorophenyl - -

190 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

191 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chloro-5-fluorophenyl

192 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

193 0 CH 2 CH 3 2,4,6-trifluorophenyl 3 -chloro-2-fluorophenyl

194 0 CH 2 CH 3 2,4,6-trifluorophenyl 3 -chloro-4-fluorophenyl

195 0 CH 2 CH 3 2,4,6-trifluorophenyl 3-chloro-5-fluorophenyl

196 0 CH 2 CH 3 2,4,6-trifluorophenyl 3 -chloro-6-fluorophenyl

197 0 CH 2 CH 3 2,4,6-trifluorophenyl 4-chloro-2-fluorophenyl

198 0 CH 2 CH 3 2,4,6-trifluorophenyl 4-chloro-3 -fluorophenyl

199 0 CH 2 CH 3 2,4,6-trifluorophenyl 2,5-dichlorophenyl

200 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

201 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-bromo-4-fluorophenyl

202 0 CH 2 CH 3 2,4,6-trifluorophenyl 2-bromo-5-fluorophenyl

203 0 CH 2 CH 3 2,4,6-trifluorophenyl 4-fluoro-2-methylphenyl

204 0 CH 2 CH 3 2,4,6-trifluorophenyl 5-fluoro-2-methylphenyl

205 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-fluorophenyl

206 0 CH 2 CH 3 3,5-dimethoxyphenyl 3 -fluorophenyl

207 0 CH 2 CH 3 3,5-dimethoxyphenyl 4-fluorophenyl

208 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chlorophenyl

209 0 CH 2 CH 3 3,5-dimethoxyphenyl 3-chlorophenyl

210 0 CH 2 CH 3 3,5-dimethoxyphenyl 4-chlorophenyl

211 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,3 -difluorophenyl

212 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,4-difluorophenyl

213 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,5-difluorophenyl

214 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,6-difluorophenyl

215 0 CH 2 CH 3 3,5-dimethoxyphenyl 3 ,4-difluorophenyl

216 0 CH 2 CH 3 3,5-dimethoxyphenyl 3,5-difluorophenyl

217 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,4-dichlorophenyl

218 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,6-dichlorophenyl

219 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,4,6-trifluorophenyl

220 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chloro-3 -fluorophenyl

221 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl

222 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chloro-5-fluorophenyl

223 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

224 0 CH 2 CH 3 3,5-dimethoxyphenyl 3 -chloro-2-fluorophenyl

225 0 CH 2 CH 3 3,5-dimethoxyphenyl 3 -chloro-4-fluorophenyl - -

226 0 CH 2 CH 3 3,5-dimethoxyphenyl 3-chloro-5-fluorophenyl

227 0 CH 2 CH 3 3,5-dimethoxyphenyl 3 -chloro-6-fluorophenyl

228 0 CH 2 CH 3 3,5-dimethoxyphenyl 4-chloro-2-fluorophenyl

229 0 CH 2 CH 3 3,5-dimethoxyphenyl 4-chloro-3 -fluorophenyl

230 0 CH 2 CH 3 3,5-dimethoxyphenyl 2,5-dichlorophenyl

231 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

232 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-bromo-4-fluorophenyl

233 0 CH 2 CH 3 3,5-dimethoxyphenyl 2-bromo-5-fluorophenyl

234 0 CH 2 CH 3 3,5-dimethoxyphenyl 4-fluoro-2-methylphenyl

235 0 CH 2 CH 3 3,5-dimethoxyphenyl 5-fluoro-2-methylphenyl

236 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-fluorophenyl

237 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3 -fluorophenyl

238 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 4-fluorophenyl

239 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chlorophenyl

240 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3-chlorophenyl

241 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 4-chlorophenyl

242 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,3 -difluorophenyl

243 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,4-difluorophenyl

244 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,5-difluorophenyl

245 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,6-difluorophenyl

246 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3 ,4-difluorophenyl

247 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3,5-difluorophenyl

248 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,4-dichlorophenyl

249 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,6-dichlorophenyl

250 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,4,6-trifluorophenyl

251 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

252 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

253 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-5-fluorophenyl

254 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

255 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3 -chloro-2-fluorophenyl

256 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

257 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3-chloro-5-fluorophenyl

258 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

259 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 4-chloro-2-fluorophenyl

260 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

261 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2,5-dichlorophenyl - -

262 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

263 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-bromo-4-fluorophenyl

264 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 2-bromo-5-fluorophenyl

265 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 4-fluoro-2-methylphenyl

266 0 CH 2 CH 3 4-cyano-2,6-difluorophenyl 5-fluoro-2-methylphenyl

267 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-fluorophenyl

268 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3 -fluorophenyl

269 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 4-fluorophenyl

270 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chlorophenyl

271 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3-chlorophenyl

272 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 4-chlorophenyl

273 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,3 -difluorophenyl

274 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,4-difluorophenyl

275 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,5-difluorophenyl

276 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,6-difluorophenyl

277 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3 ,4-difluorophenyl

278 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3,5-difluorophenyl

279 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,4-dichlorophenyl

280 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,6-dichlorophenyl

281 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,4,6-trifluorophenyl

282 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

283 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

284 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-5-fluorophenyl

285 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl

286 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3 -chloro-2-fluorophenyl

287 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

288 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3-chloro-5-fluorophenyl

289 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

290 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 4-chloro-2-fluorophenyl

291 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

292 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2,5-dichlorophenyl

293 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl

294 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-bromo-4-fluorophenyl

295 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 2-bromo-5-fluorophenyl

296 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 4-fluoro-2-methylphenyl

297 0 CH 2 CH 3 4-bromo-2,6-difluorophenyl 5-fluoro-2-methylphenyl - 5 -

298 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-fluorophenyl

299 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3 -fluorophenyl

300 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 4-fluorophenyl

301 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chlorophenyl

302 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3-chlorophenyl

303 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 4-chlorophenyl

304 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,3 -difluorophenyl

305 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,4-difluorophenyl

306 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,5-difluorophenyl

307 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,6-difluorophenyl

308 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3 ,4-difluorophenyl

309 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3,5-difluorophenyl

310 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,4-dichlorophenyl

311 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,6-dichlorophenyl

312 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,4,6-trifluorophenyl

313 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-3 -fluorophenyl

314 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

315 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-5-fluorophenyl

316 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

317 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3 -chloro-2-fluorophenyl

318 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3 -chloro-4-fluorophenyl

319 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3-chloro-5-fluorophenyl

320 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 3 -chloro-6-fluorophenyl

321 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 4-chloro-2-fluorophenyl

322 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 4-chloro-3 -fluorophenyl

323 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2,5-dichlorophenyl

324 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

325 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-bromo-4-fluorophenyl

326 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 2-bromo-5-fluorophenyl

327 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 4-fluoro-2-methylphenyl

328 0 CH 2 CH 3 2,6-difluoro-4-methylphenyl 5-fluoro-2-methylphenyl

329 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-fluorophenyl

330 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3 -fluorophenyl

331 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 4-fluorophenyl

332 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chlorophenyl

333 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3-chlorophenyl - -

334 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 4-chlorophenyl

335 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,3 -difluorophenyl

336 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,4-difluorophenyl

337 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,5-difluorophenyl

338 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,6-difluorophenyl

339 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3 ,4-difluorophenyl

340 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3,5-difluorophenyl

341 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,4-dichlorophenyl

342 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,6-dichlorophenyl

343 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,4,6-trifluorophenyl

344 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chloro-3 -fluorophenyl

345 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chloro-4-fluorophenyl

346 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chloro-5-fluorophenyl

347 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chloro-6-fluorophenyl

348 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3 -chloro-2-fluorophenyl

349 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3 -chloro-4-fluorophenyl

350 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3-chloro-5-fluorophenyl

351 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 3 -chloro-6-fluorophenyl

352 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 4-chloro-2-fluorophenyl

353 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 4-chloro-3 -fluorophenyl

354 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2,5-dichlorophenyl

355 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-chloro-6-fluorophenyl

356 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-bromo-4-fluorophenyl

357 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 2-bromo-5-fluorophenyl

358 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 4-fluoro-2-methylphenyl

359 0 CH 2 CH 3 2,6-difluoro-4-allyloxyphenyl 5-fluoro-2-methylphenyl

360 0 CH 2 CI 4-chloro-2-fluorophenyl 2-fluorophenyl

361 0 CH 2 CI 4-chloro-2-fluorophenyl 3 -fluorophenyl

362 0 CH 2 CI 4-chloro-2-fluorophenyl 4-fluorophenyl

363 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chlorophenyl

364 0 CH 2 CI 4-chloro-2-fluorophenyl 3-chlorophenyl

365 0 CH 2 CI 4-chloro-2-fluorophenyl 4-chlorophenyl

366 0 CH 2 CI 4-chloro-2-fluorophenyl 2,3 -difluorophenyl

367 0 CH 2 CI 4-chloro-2-fluorophenyl 2,4-difluorophenyl

368 0 CH 2 CI 4-chloro-2-fluorophenyl 2,5-difluorophenyl

369 0 CH 2 CI 4-chloro-2-fluorophenyl 2,6-difluorophenyl - 7 -

370 0 CH 2 CI 4-chloro-2-fluorophenyl 3 ,4-difluorophenyl

371 0 CH 2 CI 4-chloro-2-fluorophenyl 3,5-difluorophenyl

372 0 CH 2 CI 4-chloro-2-fluorophenyl 2,4-dichlorophenyl

373 0 CH 2 CI 4-chloro-2-fluorophenyl 2,6-dichlorophenyl

374 0 CH 2 CI 4-chloro-2-fluorophenyl 2,4,6-trifluorophenyl

375 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chloro-3 -fluorophenyl

376 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

377 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chloro-5-fluorophenyl

378 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

379 0 CH 2 CI 4-chloro-2-fluorophenyl 3 -chloro-2-fluorophenyl

380 0 CH 2 CI 4-chloro-2-fluorophenyl 3 -chloro-4-fluorophenyl

381 0 CH 2 CI 4-chloro-2-fluorophenyl 3-chloro-5-fluorophenyl

382 0 CH 2 CI 4-chloro-2-fluorophenyl 3 -chloro-6-fluorophenyl

383 0 CH 2 CI 4-chloro-2-fluorophenyl 4-chloro-2-fluorophenyl

384 0 CH 2 CI 4-chloro-2-fluorophenyl 4-chloro-3 -fluorophenyl

385 0 CH 2 CI 4-chloro-2-fluorophenyl 2,5-dichlorophenyl

386 0 CH 2 CI 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

387 0 CH 2 CI 4-chloro-2-fluorophenyl 2-bromo-4-fluorophenyl

388 0 CH 2 CI 4-chloro-2-fluorophenyl 2-bromo-5-fluorophenyl

389 0 CH 2 CI 4-chloro-2-fluorophenyl 4-fluoro-2-methylphenyl

390 0 CH 2 CI 4-chloro-2-fluorophenyl 5-fluoro-2-methylphenyl

391 0 CH 2 CI 2-chloro-4-fluorophenyl 2-fluorophenyl

392 0 CH 2 CI 2-chloro-4-fluorophenyl 3 -fluorophenyl

393 0 CH 2 CI 2-chloro-4-fluorophenyl 4-fluorophenyl

394 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chlorophenyl

395 0 CH 2 CI 2-chloro-4-fluorophenyl 3-chlorophenyl

396 0 CH 2 CI 2-chloro-4-fluorophenyl 4-chlorophenyl

397 0 CH 2 CI 2-chloro-4-fluorophenyl 2,3 -difluorophenyl

398 0 CH 2 CI 2-chloro-4-fluorophenyl 2,4-difluorophenyl

399 0 CH 2 CI 2-chloro-4-fluorophenyl 2,5-difluorophenyl

400 0 CH 2 CI 2-chloro-4-fluorophenyl 2,6-difluorophenyl

401 0 CH 2 CI 2-chloro-4-fluorophenyl 3 ,4-difluorophenyl

402 0 CH 2 CI 2-chloro-4-fluorophenyl 3,5-difluorophenyl

403 0 CH 2 CI 2-chloro-4-fluorophenyl 2,4-dichlorophenyl

404 0 CH 2 CI 2-chloro-4-fluorophenyl 2,6-dichlorophenyl

405 0 CH 2 CI 2-chloro-4-fluorophenyl 2,4,6-trifluorophenyl - -

406 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chloro-3 -fluorophenyl

407 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

408 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chloro-5-fluorophenyl

409 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

410 0 CH 2 CI 2-chloro-4-fluorophenyl 3 -chloro-2-fluorophenyl

411 0 CH 2 CI 2-chloro-4-fluorophenyl 3 -chloro-4-fluorophenyl

412 0 CH 2 CI 2-chloro-4-fluorophenyl 3-chloro-5-fluorophenyl

413 0 CH 2 CI 2-chloro-4-fluorophenyl 3 -chloro-6-fluorophenyl

414 0 CH 2 CI 2-chloro-4-fluorophenyl 4-chloro-2-fluorophenyl

415 0 CH 2 CI 2-chloro-4-fluorophenyl 4-chloro-3 -fluorophenyl

416 0 CH 2 CI 2-chloro-4-fluorophenyl 2,5-dichlorophenyl

417 0 CH 2 CI 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

418 0 CH 2 CI 2-chloro-4-fluorophenyl 2-bromo-4-fluorophenyl

419 0 CH 2 CI 2-chloro-4-fluorophenyl 2-bromo-5-fluorophenyl

420 0 CH 2 CI 2-chloro-4-fluorophenyl 4-fluoro-2-methylphenyl

421 0 CH 2 CI 2-chloro-4-fluorophenyl 5-fluoro-2-methylphenyl

422 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-fluorophenyl

423 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3 -fluorophenyl

424 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 4-fluorophenyl

425 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chlorophenyl

426 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3-chlorophenyl

427 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 4-chlorophenyl

428 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,3 -difluorophenyl

429 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,4-difluorophenyl

430 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,5-difluorophenyl

431 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,6-difluorophenyl

432 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3 ,4-difluorophenyl

433 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3,5-difluorophenyl

434 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,4-dichlorophenyl

435 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,6-dichlorophenyl

436 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,4,6-trifluorophenyl

437 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

438 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

439 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-5-fluorophenyl

440 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

441 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3 -chloro-2-fluorophenyl - -

442 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

443 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3-chloro-5-fluorophenyl

444 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

445 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 4-chloro-2-fluorophenyl

446 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

447 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2,5-dichlorophenyl

448 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

449 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-bromo-4-fluorophenyl

450 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 2-bromo-5-fluorophenyl

451 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 4-fluoro-2-methylphenyl

452 0 CH 2 CI 4-allyloxy-2,6-difluorophenyl 5-fluoro-2-methylphenyl

2,6-difluoro-4-

453 0 CH 2 CI 2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

454 0 CH 2 CI 3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

455 0 CH 2 CI 4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

456 0 CH 2 CI 2-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

457 0 CH 2 CI 3-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

458 0 CH 2 CI 4-chlorophenyl propargyloxyphenyl

2,6-difluoro-4-

459 0 CH 2 CI 2,3 -difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

460 0 CH 2 CI 2,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

461 0 CH 2 CI 2,5-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

462 0 CH 2 CI 2,6-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

463 0 CH 2 CI 3 ,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

464 0 CH 2 CI 3,5-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

465 0 CH 2 CI 2,4-dichlorophenyl propargyloxyphenyl - -

2,6-difluoro-4-

466 0 CH 2 CI 2,6-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

467 0 CH 2 CI 2,4,6-trifluorophenyl propargyloxyphenyl

2,6-difluoro-4-

468 0 CH 2 CI 2-chloro-3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

469 0 CH 2 CI 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

470 0 CH 2 CI 2-chloro-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

471 0 CH 2 CI 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

472 0 CH 2 CI 3 -chloro-2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

473 0 CH 2 CI 3 -chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

474 0 CH 2 CI 3-chloro-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

475 0 CH 2 CI 3 -chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

476 0 CH 2 CI 4-chloro-2-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

477 0 CH 2 CI 4-chloro-3 -fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

478 0 CH 2 CI 2,5-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

479 0 CH 2 CI 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

480 0 CH 2 CI 2-bromo-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

481 0 CH 2 CI 2-bromo-5-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

482 0 CH 2 CI 4-fluoro-2-methylphenyl propargyloxyphenyl

2,6-difluoro-4-

483 0 CH 2 CI 5-fluoro-2-methylphenyl propargyloxyphenyl

484 0 CH 2 CI 2,6-difluoro-4- 2-fluorophenyl - - methoxyphenyl

2,6-difluoro-4-

485 0 CH 2 CI 3 -fluorophenyl methoxyphenyl

2,6-difluoro-4-

486 0 CH 2 CI 4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

487 0 CH 2 CI 2-chlorophenyl methoxyphenyl

2,6-difluoro-4-

488 0 CH 2 CI 3-chlorophenyl methoxyphenyl

2,6-difluoro-4-

489 0 CH 2 CI 4-chlorophenyl methoxyphenyl

2,6-difluoro-4-

490 0 CH 2 CI 2,3 -difluorophenyl methoxyphenyl

2,6-difluoro-4-

491 0 CH 2 CI 2,4-difluorophenyl methoxyphenyl

2,6-difluoro-4-

492 0 CH 2 CI 2,5-difluorophenyl methoxyphenyl

2,6-difluoro-4-

493 0 CH 2 CI 2,6-difluorophenyl methoxyphenyl

2,6-difluoro-4-

494 0 CH 2 CI 3 ,4-difluorophenyl methoxyphenyl

2,6-difluoro-4-

495 0 CH 2 CI 3,5-difluorophenyl methoxyphenyl

2,6-difluoro-4-

496 0 CH 2 CI 2,4-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

497 0 CH 2 CI 2,6-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

498 0 CH 2 CI 2,4,6-trifluorophenyl methoxyphenyl

2,6-difluoro-4-

499 0 CH 2 CI 2-chloro-3 -fluorophenyl methoxyphenyl

2,6-difluoro-4-

500 0 CH 2 CI 2-chloro-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

501 0 CH 2 CI 2-chloro-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

502 0 CH 2 CI 2-chloro-6-fluorophenyl methoxyphenyl - -

2,6-difluoro-4-

503 0 CH 2 CI 3 -chloro-2-fluorophenyl methoxyphenyl

2,6-difluoro-4-

504 0 CH 2 CI 3 -chloro-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

505 0 CH 2 CI 3-chloro-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

506 0 CH 2 CI 3 -chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

507 0 CH 2 CI 4-chloro-2-fluorophenyl methoxyphenyl

2,6-difluoro-4-

508 0 CH 2 CI 4-chloro-3 -fluorophenyl methoxyphenyl

2,6-difluoro-4-

509 0 CH 2 CI 2,5-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

510 0 CH 2 CI 2-chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

511 0 CH 2 CI 2-bromo-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

512 0 CH 2 CI 2-bromo-5-fluorophenyl methoxyphenyl

2,6-difluoro-4-

513 0 CH 2 CI 4-fluoro-2-methylphenyl methoxyphenyl

2,6-difluoro-4-

514 0 CH 2 CI 5-fluoro-2-methylphenyl methoxyphenyl

515 0 CH 2 CI 2,4,6-trifluorophenyl 2-fluorophenyl

516 0 CH 2 CI 2,4,6-trifluorophenyl 3 -fluorophenyl

517 0 CH 2 CI 2,4,6-trifluorophenyl 4-fluorophenyl

518 0 CH 2 CI 2,4,6-trifluorophenyl 2-chlorophenyl

519 0 CH 2 CI 2,4,6-trifluorophenyl 3-chlorophenyl

520 0 CH 2 CI 2,4,6-trifluorophenyl 4-chlorophenyl

521 0 CH 2 CI 2,4,6-trifluorophenyl 2,3 -difluorophenyl

522 0 CH 2 CI 2,4,6-trifluorophenyl 2,4-difluorophenyl

523 0 CH 2 CI 2,4,6-trifluorophenyl 2,5-difluorophenyl

524 0 CH 2 CI 2,4,6-trifluorophenyl 2,6-difluorophenyl

525 0 CH 2 CI 2,4,6-trifluorophenyl 3 ,4-difluorophenyl

526 0 CH 2 CI 2,4,6-trifluorophenyl 3,5-difluorophenyl - -

527 0 CH 2 CI 2,4,6-trifluorophenyl 2,4-dichlorophenyl

528 0 CH 2 CI 2,4,6-trifluorophenyl 2,6-dichlorophenyl

529 0 CH 2 CI 2,4,6-trifluorophenyl 2,4,6-trifluorophenyl

530 0 CH 2 CI 2,4,6-trifluorophenyl 2-chloro-3 -fluorophenyl

531 0 CH 2 CI 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

532 0 CH 2 CI 2,4,6-trifluorophenyl 2-chloro-5-fluorophenyl

533 0 CH 2 CI 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

534 0 CH 2 CI 2,4,6-trifluorophenyl 3 -chloro-2-fluorophenyl

535 0 CH 2 CI 2,4,6-trifluorophenyl 3 -chloro-4-fluorophenyl

536 0 CH 2 CI 2,4,6-trifluorophenyl 3-chloro-5-fluorophenyl

537 0 CH 2 CI 2,4,6-trifluorophenyl 3 -chloro-6-fluorophenyl

538 0 CH 2 CI 2,4,6-trifluorophenyl 4-chloro-2-fluorophenyl

539 0 CH 2 CI 2,4,6-trifluorophenyl 4-chloro-3 -fluorophenyl

540 0 CH 2 CI 2,4,6-trifluorophenyl 2,5-dichlorophenyl

541 0 CH 2 CI 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

542 0 CH 2 CI 2,4,6-trifluorophenyl 2-bromo-4-fluorophenyl

543 0 CH 2 CI 2,4,6-trifluorophenyl 2-bromo-5-fluorophenyl

544 0 CH 2 CI 2,4,6-trifluorophenyl 4-fluoro-2-methylphenyl

545 0 CH 2 CI 2,4,6-trifluorophenyl 5-fluoro-2-methylphenyl

546 0 CH 2 CI 3,5-dimethoxyphenyl 2-fluorophenyl

547 0 CH 2 CI 3,5-dimethoxyphenyl 3 -fluorophenyl

548 0 CH 2 CI 3,5-dimethoxyphenyl 4-fluorophenyl

549 0 CH 2 CI 3,5-dimethoxyphenyl 2-chlorophenyl

550 0 CH 2 CI 3,5-dimethoxyphenyl 3-chlorophenyl

551 0 CH 2 CI 3,5-dimethoxyphenyl 4-chlorophenyl

552 0 CH 2 CI 3,5-dimethoxyphenyl 2,3 -difluorophenyl

553 0 CH 2 CI 3,5-dimethoxyphenyl 2,4-difluorophenyl

554 0 CH 2 CI 3,5-dimethoxyphenyl 2,5-difluorophenyl

555 0 CH 2 CI 3,5-dimethoxyphenyl 2,6-difluorophenyl

556 0 CH 2 CI 3,5-dimethoxyphenyl 3 ,4-difluorophenyl

557 0 CH 2 CI 3,5-dimethoxyphenyl 3,5-difluorophenyl

558 0 CH 2 CI 3,5-dimethoxyphenyl 2,4-dichlorophenyl

559 0 CH 2 CI 3,5-dimethoxyphenyl 2,6-dichlorophenyl

560 0 CH 2 CI 3,5-dimethoxyphenyl 2,4,6-trifluorophenyl

561 0 CH 2 CI 3,5-dimethoxyphenyl 2-chloro-3 -fluorophenyl

562 0 CH 2 CI 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl - -

563 0 CH 2 CI 3,5-dimethoxyphenyl 2-chloro-5-fluorophenyl

564 0 CH 2 CI 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

565 0 CH 2 CI 3,5-dimethoxyphenyl 3 -chloro-2-fluorophenyl

566 0 CH 2 CI 3,5-dimethoxyphenyl 3 -chloro-4-fluorophenyl

567 0 CH 2 CI 3,5-dimethoxyphenyl 3-chloro-5-fluorophenyl

568 0 CH 2 CI 3,5-dimethoxyphenyl 3 -chloro-6-fluorophenyl

569 0 CH 2 CI 3,5-dimethoxyphenyl 4-chloro-2-fluorophenyl

570 0 CH 2 CI 3,5-dimethoxyphenyl 4-chloro-3 -fluorophenyl

571 0 CH 2 CI 3,5-dimethoxyphenyl 2,5-dichlorophenyl

572 0 CH 2 CI 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

573 0 CH 2 CI 3,5-dimethoxyphenyl 2-bromo-4-fluorophenyl

574 0 CH 2 CI 3,5-dimethoxyphenyl 2-bromo-5-fluorophenyl

575 0 CH 2 CI 3,5-dimethoxyphenyl 4-fluoro-2-methylphenyl

576 0 CH 2 CI 3,5-dimethoxyphenyl 5-fluoro-2-methylphenyl

577 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-fluorophenyl

578 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3 -fluorophenyl

579 0 CH 2 CI 4-cyano-2,6-difluorophenyl 4-fluorophenyl

580 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chlorophenyl

581 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3-chlorophenyl

582 0 CH 2 CI 4-cyano-2,6-difluorophenyl 4-chlorophenyl

583 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,3 -difluorophenyl

584 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,4-difluorophenyl

585 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,5-difluorophenyl

586 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,6-difluorophenyl

587 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3 ,4-difluorophenyl

588 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3,5-difluorophenyl

589 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,4-dichlorophenyl

590 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,6-dichlorophenyl

591 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,4,6-trifluorophenyl

592 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

593 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

594 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-5-fluorophenyl

595 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

596 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3 -chloro-2-fluorophenyl

597 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

598 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3-chloro-5-fluorophenyl - 5 -

599 0 CH 2 CI 4-cyano-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

600 0 CH 2 CI 4-cyano-2,6-difluorophenyl 4-chloro-2-fluorophenyl

601 0 CH 2 CI 4-cyano-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

602 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2,5-dichlorophenyl

603 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

604 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-bromo-4-fluorophenyl

605 0 CH 2 CI 4-cyano-2,6-difluorophenyl 2-bromo-5-fluorophenyl

606 0 CH 2 CI 4-cyano-2,6-difluorophenyl 4-fluoro-2-methylphenyl

607 0 CH 2 CI 4-cyano-2,6-difluorophenyl 5-fluoro-2-methylphenyl

608 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-fluorophenyl

609 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3 -fluorophenyl

610 0 CH 2 CI 4-bromo-2,6-difluorophenyl 4-fluorophenyl

611 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chlorophenyl

612 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3-chlorophenyl

613 0 CH 2 CI 4-bromo-2,6-difluorophenyl 4-chlorophenyl

614 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,3 -difluorophenyl

615 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,4-difluorophenyl

616 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,5-difluorophenyl

617 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,6-difluorophenyl

618 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3 ,4-difluorophenyl

619 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3,5-difluorophenyl

620 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,4-dichlorophenyl

621 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,6-dichlorophenyl

622 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,4,6-trifluorophenyl

623 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-3 -fluorophenyl

624 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

625 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-5-fluorophenyl

626 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl

627 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3 -chloro-2-fluorophenyl

628 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3 -chloro-4-fluorophenyl

629 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3-chloro-5-fluorophenyl

630 0 CH 2 CI 4-bromo-2,6-difluorophenyl 3 -chloro-6-fluorophenyl

631 0 CH 2 CI 4-bromo-2,6-difluorophenyl 4-chloro-2-fluorophenyl

632 0 CH 2 CI 4-bromo-2,6-difluorophenyl 4-chloro-3 -fluorophenyl

633 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2,5-dichlorophenyl

634 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl - -

635 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-bromo-4-fluorophenyl

636 0 CH 2 CI 4-bromo-2,6-difluorophenyl 2-bromo-5-fluorophenyl

637 0 CH 2 CI 4-bromo-2,6-difluorophenyl 4-fluoro-2-methylphenyl

638 0 CH 2 CI 4-bromo-2,6-difluorophenyl 5-fluoro-2-methylphenyl

639 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-fluorophenyl

640 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3 -fluorophenyl

641 0 CH 2 CI 2,6-difluoro-4-methylphenyl 4-fluorophenyl

642 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chlorophenyl

643 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3-chlorophenyl

644 0 CH 2 CI 2,6-difluoro-4-methylphenyl 4-chlorophenyl

645 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,3 -difluorophenyl

646 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,4-difluorophenyl

647 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,5-difluorophenyl

648 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,6-difluorophenyl

649 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3 ,4-difluorophenyl

650 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3,5-difluorophenyl

651 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,4-dichlorophenyl

652 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,6-dichlorophenyl

653 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,4,6-trifluorophenyl

654 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-3 -fluorophenyl

655 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

656 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-5-fluorophenyl

657 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

658 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3 -chloro-2-fluorophenyl

659 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3 -chloro-4-fluorophenyl

660 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3-chloro-5-fluorophenyl

661 0 CH 2 CI 2,6-difluoro-4-methylphenyl 3 -chloro-6-fluorophenyl

662 0 CH 2 CI 2,6-difluoro-4-methylphenyl 4-chloro-2-fluorophenyl

663 0 CH 2 CI 2,6-difluoro-4-methylphenyl 4-chloro-3 -fluorophenyl

664 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2,5-dichlorophenyl

665 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

666 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-bromo-4-fluorophenyl

667 0 CH 2 CI 2,6-difluoro-4-methylphenyl 2-bromo-5-fluorophenyl

668 0 CH 2 CI 2,6-difluoro-4-methylphenyl 4-fluoro-2-methylphenyl

669 0 CH 2 CI 2,6-difluoro-4-methylphenyl 5-fluoro-2-methylphenyl

670 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-fluorophenyl - 7 -

671 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3 -fluorophenyl

672 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 4-fluorophenyl

673 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chlorophenyl

674 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3-chlorophenyl

675 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 4-chlorophenyl

676 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,3 -difluorophenyl

677 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,4-difluorophenyl

678 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,5-difluorophenyl

679 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,6-difluorophenyl

680 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3 ,4-difluorophenyl

681 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3,5-difluorophenyl

682 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,4-dichlorophenyl

683 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,6-dichlorophenyl

684 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,4,6-trifluorophenyl

685 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chloro-3 -fluorophenyl

686 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chloro-4-fluorophenyl

687 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chloro-5-fluorophenyl

688 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chloro-6-fluorophenyl

689 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3 -chloro-2-fluorophenyl

690 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3 -chloro-4-fluorophenyl

691 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3-chloro-5-fluorophenyl

692 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 3 -chloro-6-fluorophenyl

693 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 4-chloro-2-fluorophenyl

694 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 4-chloro-3 -fluorophenyl

695 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2,5-dichlorophenyl

696 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-chloro-6-fluorophenyl

697 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-bromo-4-fluorophenyl

698 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 2-bromo-5-fluorophenyl

699 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 4-fluoro-2-methylphenyl

700 0 CH 2 CI 2,6-difluoro-4-allyloxyphenyl 5-fluoro-2-methylphenyl

701 NH CO CH 3 4-chloro-2-fluorophenyl ethyl

702 NH CO CH 3 4-chloro-2-fluorophenyl cyclopropyl

703 NH CO CH 3 4-chloro-2-fluorophenyl isopropyl

704 NH CO CH 3 4-chloro-2-fluorophenyl tert-butyl

705 NH CO CH 3 4-chloro-2-fluorophenyl cyclopentyl

706 NH CO CH 3 4-chloro-2-fluorophenyl methyl - -

707 NH CO CH 3 4-chloro-2-fluorophenyl 2-methoxyphenyl

708 NH CO CH 3 4-chloro-2-fluorophenyl 5-chloro-2-thienyl

709 NH CO CH 3 4-chloro-2-fluorophenyl 2,4-difluorophenyl

710 NH CO CH 3 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

711 NH CO CH 3 4-chloro-2-fluorophenyl 2,6-difluorophenyl

712 NH CO CH 3 4-chloro-2-fluorophenyl 2,4-dichlorophenyl

713 NH CO CH 3 4-chloro-2-fluorophenyl 2-(trimethylsilyl)ethyl

714 NH CO CH 3 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

715 NH CO CH 3 4-chloro-2-fluorophenyl 3 -(trifluoromethyl)phenyl

716 NH CO CH 3 2-chloro-4-fluorophenyl ethyl

717 NH CO CH 3 2-chloro-4-fluorophenyl 5-chloro-2-thienyl

718 NH CO CH 3 4-allyloxy-2,6-difluorophenyl ethyl

719 NH CO CH 3 4-allyloxy-2,6-difluorophenyl cyclopropyl

720 NH CO CH 3 4-allyloxy-2,6-difluorophenyl isopropyl

721 NH CO CH 3 4-allyloxy-2,6-difluorophenyl tert-butyl

722 NH CO CH 3 4-allyloxy-2,6-difluorophenyl cyclopentyl

723 NH CO CH 3 4-allyloxy-2,6-difluorophenyl methyl

724 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2-methoxyphenyl

725 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 5-chloro-2-thienyl

726 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2,4-difluorophenyl

727 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

728 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2,6-difluorophenyl

729 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2,4-dichlorophenyl

730 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

731 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

732 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl

2,6-difluoro-4-

733 NH CO CH 3 ethyl

propargyloxyphenyl

2,6-difluoro-4-

734 NH CO CH 3 cyclopropyl

propargyloxyphenyl

2,6-difluoro-4-

735 NH CO CH 3 isopropyl

propargyloxyphenyl

2,6-difluoro-4-

736 NH CO CH 3 tert-butyl

propargyloxyphenyl

2,6-difluoro-4-

737 NH CO CH 3 cyclopentyl

propargyloxyphenyl - -

2,6-difluoro-4-

738 NH CO CH 3 methyl

propargyloxyphenyl

2,6-difluoro-4-

739 NH CO CH 3 2-methoxyphenyl propargyloxyphenyl

2,6-difluoro-4-

740 NH CO CH 3 5-chloro-2-thienyl propargyloxyphenyl

2,6-difluoro-4-

741 NH CO CH 3 2,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

742 NH CO CH 3 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

743 NH CO CH 3 2,6-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

744 NH CO CH 3 2,4-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

745 NH CO CH 3 2-(trimethylsilyl)ethyl propargyloxyphenyl

2,6-difluoro-4-

746 NH CO CH 3 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

747 NH CO CH 3 3 -(trifluoromethyl)phenyl propargyloxyphenyl

2,6-difluoro-4-

748 NH CO CH 3 ethyl

methoxyphenyl

2,6-difluoro-4-

749 NH CO CH 3 cyclopropyl

methoxyphenyl

2,6-difluoro-4-

750 NH CO CH 3 isopropyl

methoxyphenyl

2,6-difluoro-4-

751 NH CO CH 3 tert-butyl

methoxyphenyl

2,6-difluoro-4-

752 NH CO CH 3 cyclopentyl

methoxyphenyl

2,6-difluoro-4-

753 NH CO CH 3 methyl

methoxyphenyl

2,6-difluoro-4-

754 NH CO CH 3 2-methoxyphenyl methoxyphenyl

2,6-difluoro-4-

755 NH CO CH 3 5-chloro-2-thienyl methoxyphenyl

756 NH CO CH 3 2,6-difluoro-4- 2,4-difluorophenyl - - methoxyphenyl

2,6-difluoro-4-

757 NH CO CH 3 2-chloro-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

758 NH CO CH 3 2,6-difluorophenyl methoxyphenyl

2,6-difluoro-4-

759 NH CO CH 3 2,4-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

760 NH CO CH 3 2-(trimethylsilyl)ethyl methoxyphenyl

2,6-difluoro-4-

761 NH CO CH 3 2-chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

762 NH CO CH 3 3 -(trifluoromethyl)phenyl methoxyphenyl

763 NH CO CH 3 2,4,6-trifluorophenyl ethyl

764 NH CO CH 3 2,4,6-trifluorophenyl cyclopropyl

765 NH CO CH 3 2,4,6-trifluorophenyl isopropyl

766 NH CO CH 3 2,4,6-trifluorophenyl tert-butyl

767 NH CO CH 3 2,4,6-trifluorophenyl cyclopentyl

768 NH CO CH 3 2,4,6-trifluorophenyl methyl

769 NH CO CH 3 2,4,6-trifluorophenyl 2-methoxyphenyl

770 NH CO CH 3 2,4,6-trifluorophenyl 5-chloro-2-thienyl

771 NH CO CH 3 2,4,6-trifluorophenyl 2,4-difluorophenyl

772 NH CO CH 3 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

773 NH CO CH 3 2,4,6-trifluorophenyl 2,6-difluorophenyl

774 NH CO CH 3 2,4,6-trifluorophenyl 2,4-dichlorophenyl

775 NH CO CH 3 2,4,6-trifluorophenyl 2-(trimethylsilyl)ethyl

776 NH CO CH 3 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

777 NH CO CH 3 2,4,6-trifluorophenyl 3 -(trifluoromethyl)phenyl

778 NH CO CH 3 3,5-dimethoxyphenyl ethyl

779 NH CO CH 3 3,5-dimethoxyphenyl cyclopropyl

780 NH CO CH 3 3,5-dimethoxyphenyl isopropyl

781 NH CO CH 3 3,5-dimethoxyphenyl tert-butyl

782 NH CO CH 3 3,5-dimethoxyphenyl cyclopentyl

783 NH CO CH 3 3,5-dimethoxyphenyl methyl

784 NH CO CH 3 3,5-dimethoxyphenyl 2-methoxyphenyl

785 NH CO CH 3 3,5-dimethoxyphenyl 5-chloro-2-thienyl - -

786 NH CO CH 3 3,5-dimethoxyphenyl 2,4-difluorophenyl

787 NH CO CH 3 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl

788 NH CO CH 3 3,5-dimethoxyphenyl 2,6-difluorophenyl

789 NH CO CH 3 3,5-dimethoxyphenyl 2,4-dichlorophenyl

790 NH CO CH 3 3,5-dimethoxyphenyl 2-(trimethylsilyl)ethyl

791 NH CO CH 3 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

792 NH CO CH 3 3,5-dimethoxyphenyl 3 -(trifluoromethyl)phenyl

793 NH CO CH 3 4-cyano-2,6-difluorophenyl ethyl

794 NH CO CH 3 4-cyano-2,6-difluorophenyl cyclopropyl

795 NH CO CH 3 4-cyano-2,6-difluorophenyl isopropyl

796 NH CO CH 3 4-cyano-2,6-difluorophenyl tert-butyl

797 NH CO CH 3 4-cyano-2,6-difluorophenyl cyclopentyl

798 NH CO CH 3 4-cyano-2,6-difluorophenyl methyl

799 NH CO CH 3 4-cyano-2,6-difluorophenyl 2-methoxyphenyl

800 NH CO CH 3 4-cyano-2,6-difluorophenyl 5-chloro-2-thienyl

801 NH CO CH 3 4-cyano-2,6-difluorophenyl 2,4-difluorophenyl

802 NH CO CH 3 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

803 NH CO CH 3 4-cyano-2,6-difluorophenyl 2,6-difluorophenyl

804 NH CO CH 3 4-cyano-2,6-difluorophenyl 2,4-dichlorophenyl

805 NH CO CH 3 4-cyano-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

806 NH CO CH 3 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

807 NH CO CH 3 4-cyano-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl

808 NH CO CH 3 4-bromo-2,6-difluorophenyl ethyl

809 NH CO CH 3 4-bromo-2,6-difluorophenyl cyclopropyl

810 NH CO CH 3 4-bromo-2,6-difluorophenyl isopropyl

811 NH CO CH 3 4-bromo-2,6-difluorophenyl tert-butyl

812 NH CO CH 3 4-bromo-2,6-difluorophenyl cyclopentyl

813 NH CO CH 3 4-bromo-2,6-difluorophenyl methyl

814 NH CO CH 3 4-bromo-2,6-difluorophenyl 2-methoxyphenyl

815 NH CO CH 3 4-bromo-2,6-difluorophenyl 5-chloro-2-thienyl

816 NH CO CH 3 4-bromo-2,6-difluorophenyl 2,4-difluorophenyl

817 NH CO CH 3 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

818 NH CO CH 3 4-bromo-2,6-difluorophenyl 2,6-difluorophenyl

819 NH CO CH 3 4-bromo-2,6-difluorophenyl 2,4-dichlorophenyl

820 NH CO CH 3 4-bromo-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

821 NH CO CH 3 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl - -

822 NH CO CH 3 4-bromo-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl

823 NH CO CH 3 2,6-difluoro-4-methylphenyl ethyl

824 NH CO CH 3 2,6-difluoro-4-methylphenyl cyclopropyl

825 NH CO CH 3 2,6-difluoro-4-methylphenyl isopropyl

826 NH CO CH 3 2,6-difluoro-4-methylphenyl tert-butyl

827 NH CO CH 3 2,6-difluoro-4-methylphenyl cyclopentyl

828 NH CO CH 3 2,6-difluoro-4-methylphenyl methyl

829 NH CO CH 3 2,6-difluoro-4-methylphenyl 2-methoxyphenyl

830 NH CO CH 3 2,6-difluoro-4-methylphenyl 5-chloro-2-thienyl

831 NH CO CH 3 2,6-difluoro-4-methylphenyl 2,4-difluorophenyl

832 NH CO CH 3 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

833 NH CO CH 3 2,6-difluoro-4-methylphenyl 2,6-difluorophenyl

834 NH CO CH 3 2,6-difluoro-4-methylphenyl 2,4-dichlorophenyl

835 NH CO CH 3 2,6-difluoro-4-methylphenyl 2-(trimethylsilyl)ethyl

836 NH CO CH3 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

837 NH CO CH3 2,6-difluoro-4-methylphenyl 3 -(trifluoromethyl)phenyl

838 NH CO CI 4-chloro-2-fluorophenyl ethyl

839 NH CO CI 4-chloro-2-fluorophenyl cyclopropyl

840 NH CO CI 4-chloro-2-fluorophenyl isopropyl

841 NH CO CI 4-chloro-2-fluorophenyl tert-butyl

842 NH CO CI 4-chloro-2-fluorophenyl cyclopentyl

843 NH CO CI 4-chloro-2-fluorophenyl methyl

844 NH CO CI 4-chloro-2-fluorophenyl 2-methoxyphenyl

845 NH CO CI 4-chloro-2-fluorophenyl 5-chloro-2-thienyl

846 NH CO CI 4-chloro-2-fluorophenyl 2,4-difluorophenyl

847 NH CO CI 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

848 NH CO CI 4-chloro-2-fluorophenyl 2,6-difluorophenyl

849 NH CO CI 4-chloro-2-fluorophenyl 2,4-dichlorophenyl

850 NH CO CI 4-chloro-2-fluorophenyl 2-(trimethylsilyl)ethyl

851 NH CO CI 4-chloro-2-fluorophenyl 2-chloro-6-fluorophenyl

852 NH CO CI 4-chloro-2-fluorophenyl 3 -(trifluoromethyl)phenyl

853 NH CO CI 2-chloro-4-fluorophenyl ethyl

854 NH CO CI 2-chloro-4-fluorophenyl cyclopropyl

855 NH CO CI 2-chloro-4-fluorophenyl isopropyl

856 NH CO CI 2-chloro-4-fluorophenyl tert-butyl

857 NH CO CI 2-chloro-4-fluorophenyl cyclopentyl - -

858 NH CO CI 2-chloro-4-fluorophenyl methyl

859 NH CO CI 2-chloro-4-fluorophenyl 2-methoxyphenyl

860 NH CO CI 2-chloro-4-fluorophenyl 5-chloro-2-thienyl

861 NH CO CI 2-chloro-4-fluorophenyl 2,4-difluorophenyl

862 NH CO CI 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

863 NH CO CI 2-chloro-4-fluorophenyl 2,6-difluorophenyl

864 NH CO CI 2-chloro-4-fluorophenyl 2,4-dichlorophenyl

865 NH CO CI 2-chloro-4-fluorophenyl 2-(trimethylsilyl)ethyl

866 NH CO CI 2-chloro-4-fluorophenyl 2-chloro-6-fluorophenyl

867 NH CO CI 2-chloro-4-fluorophenyl 3 -(trifluoromethyl)phenyl

868 NH CO CI 4-allyloxy-2,6-difluorophenyl ethyl

869 NH CO CI 4-allyloxy-2,6-difluorophenyl cyclopropyl

870 NH CO CI 4-allyloxy-2,6-difluorophenyl isopropyl

871 NH CO CI 4-allyloxy-2,6-difluorophenyl tert-butyl

872 NH CO CI 4-allyloxy-2,6-difluorophenyl cyclopentyl

873 NH CO CI 4-allyloxy-2,6-difluorophenyl methyl

874 NH CO CI 4-allyloxy-2,6-difluorophenyl 2-methoxyphenyl

875 NH CO CI 4-allyloxy-2,6-difluorophenyl 5-chloro-2-thienyl

876 NH CO CI 4-allyloxy-2,6-difluorophenyl 2,4-difluorophenyl

877 NH CO CI 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

878 NH CO CI 4-allyloxy-2,6-difluorophenyl 2,6-difluorophenyl

879 NH CO CI 4-allyloxy-2,6-difluorophenyl 2,4-dichlorophenyl

880 NH CO CI 4-allyloxy-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

881 NH CO CI 4-allyloxy-2,6-difluorophenyl 2-chloro-6-fluorophenyl

882 NH CO CI 4-allyloxy-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl

2,6-difluoro-4-

883 NH CO CI ethyl

propargyloxyphenyl

2,6-difluoro-4-

884 NH CO CI cyclopropyl

propargyloxyphenyl

2,6-difluoro-4-

885 NH CO CI isopropyl

propargyloxyphenyl

2,6-difluoro-4-

886 NH CO CI tert-butyl

propargyloxyphenyl

2,6-difluoro-4-

887 NH CO CI cyclopentyl

propargyloxyphenyl

888 NH CO CI 2,6-difluoro-4- methyl - - propargyloxyphenyl

2,6-difluoro-4-

889 NH CO CI 2-methoxyphenyl propargyloxyphenyl

2,6-difluoro-4-

890 NH CO CI 5-chloro-2-thienyl propargyloxyphenyl

2,6-difluoro-4-

891 NH CO CI 2,4-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

892 NH CO CI 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

893 NH CO CI 2,6-difluorophenyl propargyloxyphenyl

2,6-difluoro-4-

894 NH CO CI 2,4-dichlorophenyl propargyloxyphenyl

2,6-difluoro-4-

895 NH CO CI 2-(trimethylsilyl)ethyl propargyloxyphenyl

2,6-difluoro-4-

896 NH CO CI 2-chloro-6-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

897 NH CO CI 3 -(trifluoromethyl)phenyl propargyloxyphenyl

2,6-difluoro-4-

898 NH CO CI ethyl

methoxyphenyl

2,6-difluoro-4-

899 NH CO CI cyclopropyl

methoxyphenyl

2,6-difluoro-4-

900 NH CO CI isopropyl

methoxyphenyl

2,6-difluoro-4-

901 NH CO CI tert-butyl

methoxyphenyl

2,6-difluoro-4-

902 NH CO CI cyclopentyl

methoxyphenyl

2,6-difluoro-4-

903 NH CO CI methyl

methoxyphenyl

2,6-difluoro-4-

904 NH CO CI 2-methoxyphenyl methoxyphenyl

2,6-difluoro-4-

905 NH CO CI 5-chloro-2-thienyl methoxyphenyl

2,6-difluoro-4-

906 NH CO CI 2,4-difluorophenyl methoxyphenyl - 5 -

2,6-difluoro-4-

907 NH CO CI 2-chloro-4-fluorophenyl methoxyphenyl

2,6-difluoro-4-

908 NH CO CI 2,6-difluorophenyl methoxyphenyl

2,6-difluoro-4-

909 NH CO CI 2,4-dichlorophenyl methoxyphenyl

2,6-difluoro-4-

910 NH CO CI 2-(trimethylsilyl)ethyl methoxyphenyl

2,6-difluoro-4-

911 NH CO CI 2-chloro-6-fluorophenyl methoxyphenyl

2,6-difluoro-4-

912 NH CO CI 3 -(trifluoromethyl)phenyl methoxyphenyl

913 NH CO CI 2,4,6-trifluorophenyl ethyl

914 NH CO CI 2,4,6-trifluorophenyl cyclopropyl

915 NH CO CI 2,4,6-trifluorophenyl isopropyl

916 NH CO CI 2,4,6-trifluorophenyl tert-butyl

917 NH CO CI 2,4,6-trifluorophenyl cyclopentyl

918 NH CO CI 2,4,6-trifluorophenyl methyl

919 NH CO CI 2,4,6-trifluorophenyl 2-methoxyphenyl

920 NH CO CI 2,4,6-trifluorophenyl 5-chloro-2-thienyl

921 NH CO CI 2,4,6-trifluorophenyl 2,4-difluorophenyl

922 NH CO CI 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

923 NH CO CI 2,4,6-trifluorophenyl 2,6-difluorophenyl

924 NH CO CI 2,4,6-trifluorophenyl 2,4-dichlorophenyl

925 NH CO CI 2,4,6-trifluorophenyl 2-(trimethylsilyl)ethyl

926 NH CO CI 2,4,6-trifluorophenyl 2-chloro-6-fluorophenyl

927 NH CO CI 2,4,6-trifluorophenyl 3 -(trifluoromethyl)phenyl

928 NH CO CI 3,5-dimethoxyphenyl ethyl

929 NH CO CI 3,5-dimethoxyphenyl cyclopropyl

930 NH CO CI 3,5-dimethoxyphenyl isopropyl

931 NH CO CI 3,5-dimethoxyphenyl tert-butyl

932 NH CO CI 3,5-dimethoxyphenyl cyclopentyl

933 NH CO CI 3,5-dimethoxyphenyl methyl

934 NH CO CI 3,5-dimethoxyphenyl 2-methoxyphenyl

935 NH CO CI 3,5-dimethoxyphenyl 5-chloro-2-thienyl

936 NH CO CI 3,5-dimethoxyphenyl 2,4-difluorophenyl - -

937 NH CO CI 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl

938 NH CO CI 3,5-dimethoxyphenyl 2,6-difluorophenyl

939 NH CO CI 3,5-dimethoxyphenyl 2,4-dichlorophenyl

940 NH CO CI 3,5-dimethoxyphenyl 2-(trimethylsilyl)ethyl

941 NH CO CI 3,5-dimethoxyphenyl 2-chloro-6-fluorophenyl

942 NH CO CI 3,5-dimethoxyphenyl 3 -(trifluoromethyl)phenyl

943 NH CO CI 4-cyano-2,6-difluorophenyl ethyl

944 NH CO CI 4-cyano-2,6-difluorophenyl cyclopropyl

945 NH CO CI 4-cyano-2,6-difluorophenyl isopropyl

946 NH CO CI 4-cyano-2,6-difluorophenyl tert-butyl

947 NH CO CI 4-cyano-2,6-difluorophenyl cyclopentyl

948 NH CO CI 4-cyano-2,6-difluorophenyl methyl

949 NH CO CI 4-cyano-2,6-difluorophenyl 2-methoxyphenyl

950 NH CO CI 4-cyano-2,6-difluorophenyl 5-chloro-2-thienyl

951 NH CO CI 4-cyano-2,6-difluorophenyl 2,4-difluorophenyl

952 NH CO CI 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

953 NH CO CI 4-cyano-2,6-difluorophenyl 2,6-difluorophenyl

954 NH CO CI 4-cyano-2,6-difluorophenyl 2,4-dichlorophenyl

955 NH CO CI 4-cyano-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

956 NH CO CI 4-cyano-2,6-difluorophenyl 2-chloro-6-fluorophenyl

957 NH CO CI 4-cyano-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl

958 NH CO CI 4-bromo-2,6-difluorophenyl ethyl

959 NH CO CI 4-bromo-2,6-difluorophenyl cyclopropyl

960 NH CO CI 4-bromo-2,6-difluorophenyl isopropyl

961 NH CO CI 4-bromo-2,6-difluorophenyl tert-butyl

962 NH CO CI 4-bromo-2,6-difluorophenyl cyclopentyl

963 NH CO CI 4-bromo-2,6-difluorophenyl methyl

964 NH CO CI 4-bromo-2,6-difluorophenyl 2-methoxyphenyl

965 NH CO CI 4-bromo-2,6-difluorophenyl 5-chloro-2-thienyl

966 NH CO CI 4-bromo-2,6-difluorophenyl 2,4-difluorophenyl

967 NH CO CI 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

968 NH CO CI 4-bromo-2,6-difluorophenyl 2,6-difluorophenyl

969 NH CO CI 4-bromo-2,6-difluorophenyl 2,4-dichlorophenyl

970 NH CO CI 4-bromo-2,6-difluorophenyl 2-(trimethylsilyl)ethyl

971 NH CO CI 4-bromo-2,6-difluorophenyl 2-chloro-6-fluorophenyl

972 NH CO CI 4-bromo-2,6-difluorophenyl 3 -(trifluoromethyl)phenyl - 7 -

973 NH CO CI 2,6-difluoro-4-methylphenyl ethyl

974 NH CO CI 2,6-difluoro-4-methylphenyl cyclopropyl

975 NH CO CI 2,6-difluoro-4-methylphenyl isopropyl

976 NH CO CI 2,6-difluoro-4-methylphenyl tert-butyl

977 NH CO CI 2,6-difluoro-4-methylphenyl cyclopentyl

978 NH CO CI 2,6-difluoro-4-methylphenyl methyl

979 NH CO CI 2,6-difluoro-4-methylphenyl 2-methoxyphenyl

980 NH CO CI 2,6-difluoro-4-methylphenyl 5-chloro-2-thienyl

981 NH CO CI 2,6-difluoro-4-methylphenyl 2,4-difluorophenyl

982 NH CO CI 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

983 NH CO CI 2,6-difluoro-4-methylphenyl 2,6-difluorophenyl

984 NH CO CI 2,6-difluoro-4-methylphenyl 2,4-dichlorophenyl

985 NH CO CI 2,6-difluoro-4-methylphenyl 2-(trimethylsilyl)ethyl

986 NH CO CI 2,6-difluoro-4-methylphenyl 2-chloro-6-fluorophenyl

987 NH CO CI 2,6-difluoro-4-methylphenyl 3 -(trifluoromethyl)phenyl

988 NH so 2 CH 3 4-chloro-2-fluorophenyl ethyl

989 NH so 2 CH 3 2-chloro-4-fluorophenyl ethyl

990 NH so 2 CH 3 4-allyloxy-2,6-difluorophenyl ethyl

2,6-difluoro-4-

991 NH so 2 CH 3 ethyl

propargyloxyphenyl

2,6-difluoro-4-

992 NH so 2 CH 3 ethyl

methoxyphenyl

993 NH so 2 CH 3 2,4,6-trifluorophenyl ethyl

994 NH so 2 CH 3 3,5-dimethoxyphenyl ethyl

995 NH so 2 CH 3 4-cyano-2,6-difluorophenyl ethyl

996 NH so 2 CH 3 4-bromo-2,6-difluorophenyl ethyl

997 NH so 2 CH 3 2,6-difluoro-4-methylphenyl ethyl

998 NH so 2 CH 3 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

999 NH so 2 CH 3 2-chloro-4-fluorophenyl 2-chloro-4-fluorophenyl

1000 NH so 2 CH 3 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

2,6-difluoro-4-

100 NH so 2 CH 3 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

1002 NH so 2 CH 3 2-chloro-4-fluorophenyl methoxyphenyl

1003 NH so 2 CH 3 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

1004 NH so 2 CH 3 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl - -

1005 NH S0 2 CH 3 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

1006 NH S0 2 CH 3 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

1007 NH S0 2 CH 3 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

1008 NH S0 2 CI 2-chloro-4-fluorophenyl ethyl

1009 NH S0 2 CI 4-allyloxy-2,6-difluorophenyl ethyl

2,6-difluoro-4-

1010 NH S0 2 CI ethyl

propargyloxyphenyl

2,6-difluoro-4-

1011 NH S0 2 CI ethyl

methoxyphenyl

1012 NH S0 2 CI 2,4,6-trifluorophenyl ethyl

1013 NH S0 2 CI 3,5-dimethoxyphenyl ethyl

1014 NH S0 2 CI 4-cyano-2,6-difluorophenyl ethyl

1015 NH S0 2 CI 4-bromo-2,6-difluorophenyl ethyl

1016 NH S0 2 CI 2,6-difluoro-4-methylphenyl ethyl

1017 NH S0 2 CI 4-chloro-2-fluorophenyl 2-chloro-4-fluorophenyl

1018 NH S0 2 CI 4-allyloxy-2,6-difluorophenyl 2-chloro-4-fluorophenyl

2,6-difluoro-4-

1019 NH S0 2 CI 2-chloro-4-fluorophenyl propargyloxyphenyl

2,6-difluoro-4-

1020 NH S0 2 CI 2-chloro-4-fluorophenyl methoxyphenyl

1021 NH S0 2 CI 2,4,6-trifluorophenyl 2-chloro-4-fluorophenyl

1022 NH S0 2 CI 3,5-dimethoxyphenyl 2-chloro-4-fluorophenyl

1023 NH S0 2 CI 4-cyano-2,6-difluorophenyl 2-chloro-4-fluorophenyl

1024 NH S0 2 CI 4-bromo-2,6-difluorophenyl 2-chloro-4-fluorophenyl

1025 NH S0 2 CI 2,6-difluoro-4-methylphenyl 2-chloro-4-fluorophenyl

1026 NH CO CH 3 4-chloro-2-fluorophenyl 5-chloro-2-thienyl

1027 NH CO CH 3 4-allyloxy-2,6-difluorophenyl 5-chloro-2-thienyl

2,6-difluoro-4-

1028 NH CO CH 3 5-chloro-2-thienyl propargyloxyphenyl

2,6-difluoro-4-

1029 NH CO CH 3 5-chloro-2-thienyl methoxyphenyl

1030 NH CO CH 3 2,4,6-trifluorophenyl 5-chloro-2-thienyl

1031 NH CO CH 3 3,5-dimethoxyphenyl 5-chloro-2-thienyl

1032 NH CO CH 3 4-cyano-2,6-difluorophenyl 5-chloro-2-thienyl

1033 NH CO CH 3 4-bromo-2,6-difluorophenyl 5-chloro-2-thienyl

1034 NH CO CH 3 2,6-difluoro-4-methylphenyl 5-chloro-2-thienyl - -

Even more particularly preferred compounds of the formula (I) according to the present invention are those, wherein:

R is CH 3 ,

X is O or NH,

Y is a structure element selected from the group consisting of (C=0), C¾ and SO2,

Q 1 is selected from the group consisting of 2-chloro-4-fluorophenyl, 4-chloro-2-fluorophenyl, 4- allyloxy-2,6-difluorophenyl, 2,6-difluoro-4-propargyloxyphenyl, 2,6-difluoro-4-methoxyphenyl, 2,4,6-trifluorophenyl, 3,5-dimethoxyphenyl, 4-cyano-2,6-difluorophenyl, 4-bromo-2,6- difluorophenyl, and 2,6-difluoro-4-methylphenyl,

and

Q 2 is selected from the group consisting of cyclopropyl, cyclopentyl, tert-butyl, isopropyl, methyl, ethyl, 2-methoxyphenyl, 2-fluorophenyl, 2-chlorophenyl, 3 -fluorophenyl, 3-chlorophenyl, 4- fluorophenyl, 4-chlorophenyl, 2,3-difluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6- difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-3 -fluorophenyl, 2-chloro-4-fluorophenyl, 2-chloro-5-fluorophenyl, 2- chloro-6-fluorophenyl, 3-chloro-2-fluorophenyl, 3-chloro-4-fluorophenyl, 3-chloro-5-fluorophenyl, 3-chloro-6-fluorophenyl, 4-chloro-2-fluorophenyl, 4-chloro-3 -fluorophenyl, 2-bromo-4- fluorophenyl, 2-bromo-5-fluorophenyl, 4-fluoro-2-methylphenyl, 5-fluoro-2-methylphenyl, 2,4,6- trifluorophenyl, and 3-(trifluoromethyl)phenyl, wherein the following applies:

- when X is O, then Y is CH 2 ;

- when X is NH, then Y is (C=0) 5

In a further aspect, the present invention relates to a composition comprising

(a) a fungicidally effective amount of a compound of the formula (I) according to the present invention as defined herein, and one or more further constituents selected from the group consisting of groups (b) and (c): (b) agrochemically acceptable adjuvants, preferably selected from the group consisting of surfactants, liquid diluents and solid diluents, and

(c) other pesticidally active ingredients (i.e. pesticidally active ingredients not corresponding to compounds of the formula (I), tautomers and/or salts thereof according to the present invention as defined herein).

In a further aspect, the present invention preferably relates to a composition according to the present inven- tion as defined herein, comprising

(c) one or more further fungicidally active ingredients (i.e. fungicidally active ingredients not corresponding to compounds of the formula (I), tautomers and/or salts thereof according to the present invention as defined herein).

In a further aspect, the present invention relates to a method for controlling one or more plant diseases caused by fungal plant pathogens, comprising the steps of

(i) providing a compound of the formula (I) according to the present invention as defined herein or a composition according to the present invention as defined herein, and

(ii) applying to the plant, to a portion of the plant or to plant seeds a fungicidally effective amount the compound provided in step (i). In the context of the present invention, "control" or "controlling" of harmful microorganisms such as phytopathogenic fimgi means a reduction in infestation by harmful microorganisms, in particular phytopathogenic fimgi, compared with the untreated plant measured as fungicidal efficacy. Preferably, a reduction of at least 25 % (i.e. 25% or more), and more preferably a reduction of at least 50 % (i.e. 50% or more) is achieved, in each case compared to the untreated plant. Even more preferably, the infestation by harmful microorganisms, in particular phytopathogenic fungi, is suppressed by 70-100 % compared to the untreated plant. The infestation of the untreated plant in each case is defined as 100 % infestation.

In the context of the present invention, the "control" or "controlling" of harmful microorganisms, in particular phytopathogenic fimgi, may be curative, i.e. for treatment of already infected plants, or protective, i.e. for protection of plants which have not yet been infected. 5

More specifically, the present invention preferably relates to a method for controlling phytopathogenic harmful fungi, characterized in that one or more compounds of the formula (I) according to the present invention are applied to the phytopathogenic harmful fungi and/or their habitat.

In a further aspect, the present invention relates to the use of one or more compounds of the formula (I) ac- cording to the present invention or of compositions according to the present invention for controlling fungi, preferably for controlling fungi in plants or plant seeds.

In a further aspect, the present invention preferably relates to the use of one or more compounds of the formula (I) according to the present invention or of compositions according to the present invention for control of phytopathogenic harmful fungi. The compounds of the formula (I) according to the invention showed remarkable efficacy against various phytopathogenic harmful fungi, inter alia against species selected from the group consisting of Puccinia spp., Septoria spp., and Sphaerotheca spp., in particular against Septoria spp..

The compounds of the formula (I) according to the invention allowed remarkable control of species selected from the group of Puccinia recondita, Septoria tritici, and Sphaerotheca fuliginea. As described in more detail in the biological examples below, the compounds of the formula (I) according to the invention showed remarkable efficacy in controlling Puccinia recondita (brown rust) on wheat, Septoria tritici (leaf spot) on wheat, and Sphaerotheca fuliginea (powdery mildew) on cucurbits.

In a further aspect, the present invention preferably relates to the use of one or more compounds of the formula (I) according to the present invention or of compositions according to the present invention for treat- ment of transgenic plants, of seeds and of seed of transgenic plants.

The compounds of the formula (I) according to the present invention can be obtained via different synthetic pathways and methods.

In the following synthetic methods are described that may be used to obtain the compounds of the formula (I) according to the present invention. The different synthetic methods are also summarized in the follow- ing schemes. In said schemes R, X, Y, Q 1 and Q 2 correspond to R, X, Y, Q 1 and Q 2 as defined herein for the compounds of the formula (I) according to the present invention.

The abbreviations used in the context of the present invention are explained in the Examples below.

In the following synthetic methods and schemes "LG" represents a leaving group. Suitable leaving groups LG are in general sulfonyl esters like methane sulfonate, p-toluene sulfonate, triflate or similar, halogens, pseudohalogens or specific heterocycles such as N-bound imidazolyl, pyrazolyl, hydroxybenzotriazolyl- or 5 similar groups. Leaving groups can also be carboxylic esters such as acetyloxy, pivaloyloxy, trifluoroace- tyloxy groups or similar groups, or phosphonates.

The compounds of the formula (I) according to the present invention may be obtained as shown in the following Scheme 1.

Scheme 1 : Synthesis of compounds of the formula (I) according to the present invention

(Z-a) (I)

According to a further aspect of the present invention, the present invention relates to a method for producing a compound of formula (I) as defined herein, characterized by the following steps: providing a compound of the formula (Z-a)

(Z-a) wherein R, X, and Q 1 each have the meaning as defined herein,

(ii) providing a compound of the formula (Z-b)

Q 2 -Y

LG

(Z-b) wherein Q 2 has the meaning as defined herein, and wherein LG is a leaving group,

(iii) reacting compounds (Z-a) and (Z-b), thereby obtaining a compound of the formula (I) according to the present invention as defined herein. 5

The skilled person in organic synthesis is well familiar with the reactions and the conditions under which said reactions can be carried out (see textbooks of organic chemistry, e.g. March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th edition, 2007, Wiley-Interscience and the references cited therein).

Preferred leaving groups LG are selected from the group consisting of sulfonyl esters (preferably methane sulfonate, p-toluene sulfonate, triflate or similar), halogens (preferably CI, Br or I), pseudohalogens, suitable heterocycles (preferably N-bound imidazolyl, pyrazole, hydroxybenzotriazolyl- or similar groups), car- boxylic esters (preferably acetyloxy, pivaloyloxy, trifluoroacetyloxy groups or similar groups), and phos- phonate esters or anhydrides (preferably propanephosphonates).

The reaction of compounds (Z-a) and (Z-b) may be carried out in the presence of a base, preferably selected from the group consisting of DIPEA, TEA, NMO, DBU, sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, potassium tert-butoxide, sodium ethoxide, and sodium methoxide.

Depending on the linkers X and Y in the compounds of the formula (I) according to the present invention, different synthetic methods may be used to obtain the compounds of the formula (I). The synthetic methods illustrated in the following schemes exemplify to the skilled person which synthetic pathways and methodologies may be used to synthesize the compounds of the formula (I) according to the present invention.

Scheme 2: Synthesis of compounds of the formula (I) according to the present invention wherein X = O and Y = CH 2

(Z-i) ( I )

Compounds of the formula (I) according to the present invention wherein X = O and Y = C¾ can be obtained by nucleophilic substitution reaction of intermediates of the formula (Z-i) with compounds of the formula (Z-ii). Preferred leaving groups LG in compounds of the formula (Z-ii) for these reactions are chloride, bromide, methane sulfonate (mesylate), toluene sulfonate (tosylate) and trifluoromethane sulfonate (triflate). The reaction preferably is conducted either without any solvent, or if a solvent is used, preferably a polar aprotic solvent is used, preferable THF, DMF, DMSO, DMPU or acetone at ambient temperature (about 20°C) or above. The reaction may be carried out in the presence of a base, such as DIPEA, TEA, NMO, DBU, sodium hydride, sodium hydroxide, sodium carbonate, potassium carbonate, po- 5 tassium tert-butoxide, sodium ethoxide, or sodium methoxide. In a preferred method, the compound of the formula (I) is dissolved in DMF or THF, treated with 1 equivalent or an excess of a base, preferably sodium hydride, and is then reacted with compound of the formula (Z-ii) to provide the compounds of the formula (I) according to the present invention. Scheme 3 : Synthesis of compounds of the formula (I) according to the present invention wherein X = NH and Y = CO

(Z-iii) (I)

Compounds of the formula (I) according to the present invention wherein X = NH and Y = CO can be obtained by acylation reactions. For example, intermediate (Z-iii) is reacted with an acylating agent (Z-iv). Preferred leaving groups in compounds of the formula (Z-iv) for these reactions are chloride, acetyloxy, pivaloyloxy, imidazolyl, hydroxybenzotriazolyl. The acylating reagent may be prepared in situ by reacting the carboxylic acid with an activating agent such as TBTU, HATU, pivalic anhydride, phosphoryl chloride, oxalic dichloride with catalytic amounts of DMF, propanephosphonic anhydride, etc.. The reaction is preferably carried out in a solvent, preferably in a polar aprotic solvent, more preferable in THF, DMF, DMSO, DMPU, or pyridine, preferably at 0 °C, at ambient temperature (about 20°C) or above. The reaction may be carried out in the presence of a base, preferably DIPEA, TEA or NMO. The reaction may be supported by the addition of a catalytic amount of DMAP. Preferably, the reaction is carried out using propanephosphonic anhydride to prepare the mixed anhydride in situ with the compound of formula (Z-iv) and couple it directly (i.e. without isolation) with the compound of the formula (Z-iii) in the presence of TEA in THF at elevated temperature.

Scheme 4: Synthesis of compounds of the formula (I) according to the present invention wherein X = NH and Y = S0 2

(Z-iii) (I)

Compounds of the formula (I) according to the present invention wherein X = NH and Y = SO 2 can be obtained by synthesised by reacting intermediates (Z-iii) with sulfonylating agents of the formula (Z-v). Preferred sulfonylating agents are sulfonic acid chlorides (LG = CI) or sulfonic acid anhydrides (LG = OSO2Q 2 ). The sulfonylation reactions preferably takes place in a solvent, preferably in a polar aprotic solvent, more preferable in THF, DMF, DMSO, DMPU, or pyridine at 0 °C, at ambient temperature (about 20°C) or above. The reaction may be carried out in the presence of a base, for instance DIPEA, TEA or NMO. The reaction may be supported by the addition of a catalytic amount of DMAP.

Isomers Depending on the nature of the substituents, the compounds of the formula (I) may be in the form of geometric and/or optically active isomers or corresponding isomer mixtures in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers.

Methods and uses The invention also relates to a method for controlling unwanted microorganisms, characterized in that the compounds of the formula (I) are applied to the microorganisms and/or in their habitat.

The invention further relates to seed which has been treated with at least one compound of the formula (I).

The invention also provides a method for protecting seed against unwanted microorganisms by using seed treated with at least one compound of the formula (I). The compounds of the formula (I) have potent microbicidal activity and can be used for control of unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.

The compounds of the formula (I) have very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Asco- mycetes, Basidiomycetes and Deuteromycetes. Bactericides can be used in crop protection, for example, for control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

The compounds of the formula (I) can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive active ingredients or compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.

Plants

All plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which are protectable and non-protectable by plant breeders' rights. Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, nee- dies, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglan- daceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), AUiaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Bras- sicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

Pathogens 5?

Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis; Podosphaera species, for example Podosphaera leucotricha; Sphaerotheca species, for example Sphaerotheca fuliginea; Uncinula species, for example Uncinula necator; diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymno- sporangium sabinae; Hemileia species, for example Hemileia vastatrix; Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae; Puccinia species, for example Puccinia recondita, Puc- cinia graminis oder Puccinia striiformis; Uromyces species, for example Uromyces appendiculatus; diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida; Bremia species, for example Bremia lactucae; Peronospora species, for example Perono- spora pisi or P. brassicae; Phytophthora species, for example Phytophthora infestans; Plasmopara species, for example Plasmopara viticola; Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example Pythium ultimum; leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alter- naria solani; Cercospora species, for example Cercospora beticola; Cladiosporium species, for example Cladiosporium cucumerinum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, for example Colletotrichum lindemuthanium; Cycloconium species, for example Cycloconium oleaginum; Diaporthe species, for example Diaporthe citri; Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species, for example Gloeosporium laeticolor; Glomerella species, for example Glomerella cingulata; Guignardia species, for example Guignardia bidwelli; Leptosphaeria species, for example Leptosphaeria maculans; Magnaporthe species, for example Magnaporthe grisea; Microdochium species, for example Microdochi- um nivale; Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidico- la or Mycosphaerella fijiensis; Phaeosphaeria species, for example Phaeosphaeria nodorum; Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, for example Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, for example Rhynchosporium secal- is; Septoria species, for example Septoria apii or Septoria lycopersici; Stagonospora species, for example Stagonospora nodorum; Typhula species, for example Typhula incarnata; Venturia species, for example Venturia inaequalis; root and stem diseases caused, for example, by Corticium species, for example Corticium graminearum; Fusarium species, for example Fusarium oxysporum; Gaeumannomyces species, for example Gaeuman- nomyces graminis; Plasmodiophora species, for example Plasmodiophora brassicae; Rhizoctonia species, for example Rhizoctonia solani; Sarocladium species, for example Sarocladium oryzae; Sclerotium spe- 5 cies, for example Sclerotium oryzae; Tapesia species, for example Tapesia acuformis; Thielaviopsis species, for example Thielaviopsis basicola; ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example Al- ternaria spp.; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium cladosporioides; Claviceps species, for example Claviceps purpurea; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Monographella species, for example Monographella nivalis; Stagnospora species, for example Stagnospora nodorum; diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana; Tilletia species, for example Tilletia caries or Tilletia controversa; Urocystis species, for example Urocyst- is occulta; Ustilago species, for example Ustilago nuda; fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus; Botrytis species, for example Botrytis cinerea; Penicillium species, for example Penicillium expansum or Penicillium pur- purogenum; Rhizopus species, for example Rhizopus stolonifer; Sclerotinia species, for example Sclero- tinia sclerotiorum; Verticilium species, for example Verticilium alboatrum; seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicola; Aphanomyces species, for example Aphanomyces eu- teiches; Ascochyta species, for example Ascochyta lentis; Aspergillus species, for example Aspergillus flavus; Cladosporium species, for example Cladosporium herbarum; Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum spe- cies, for example Colletotrichum coccodes; Fusarium species, for example Fusarium culmorum; Gibberella species, for example Gibberella zeae; Macrophomina species, for example Macrophomina phaseolina; Microdochium species, for example Microdochium nivale; Monographella species, for example Monographella nivalis; Penicillium species, for example Penicillium expansum; Phoma species, for example Phoma lingam; Phomopsis species, for example Phomopsis sojae; Phytophthora species, for example Phytophthora cactorum; Pyrenophora species, for example Pyrenophora graminea; Pyricularia species, for example Pyricularia oryzae; Pythium species, for example Pythium ultimum; Rhizoctonia species, for example Rhizoctonia solani; Rhizopus species, for example Rhizopus oryzae; Sclerotium species, for example Sclerotium rolfsii; Septoria species, for example Septoria nodorum; Typhula species, for example Ty- phula incarnata; Verticillium species, for example Verticillium dahliae; cancers, galls and witches' broom caused, for example, by Nectria species, for example Nectria galligena; wilt diseases caused, for example, by Monilinia species, for example Monilinia laxa; deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exo- basidium vexans; Taphrina species, for example Taphrina deformans; - 5 - degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example Ganoderma boninense; diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea; diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani; Helminthosporium species, for example Helminthosporium solani; diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzae; Pseudomonas species, for example Pseudomonas syringae pv. lachrymans; Erwinia species, for example Erwinia amylovora. Preference is given to controlling the following diseases of soya beans:

Fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec, atrans tenuissima), Anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Cho- anephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), lep- tosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (My- coleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium ir- regulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola). Mycotoxins

In addition, the compounds of the formula (I) can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom. Mycotoxins include particularly, but not exclusively, the fol- lowing: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2 -toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides etc., and also by Aspergillus spec, such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec, such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec, such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spec, and others.

Material Protection

The compounds of the formula (I) can also be used in the protection of materials, for protection of industrial materials against attack and destruction by phytopathogenic fungi. In addition, the compounds of the formula (I) can be used as antifouling compositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected by inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

The compounds of the formula (I) may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

In the case of treatment of wood the compounds of the formula (I) may also be used against fungal diseas- es liable to grow on or inside timber. The term "timber" means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. The method for treating timber according to the invention mainly consists in contacting a composition according to the invention; this includes for example direct application, spraying, dipping, injection or any other suitable means. In addition, the compounds of the formula (I) can be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signalling systems, from fouling.

The compounds of the formula (I) can also be employed for protecting storage goods. Storage goods are un- derstood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, can be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The inventive compositions may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds of the formula (I) preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Peni- cillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Au- reobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paeci- lomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Sac- charomyces cerevisae.

Formulations

The present invention further relates to a composition for controlling unwanted microorganisms, comprising at least one of the compounds of the formula (I). These are preferably fungicidal compositions which comprise agriculturally suitable auxiliaries, solvents, carriers, surfactants or extenders. According to the invention, a carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better applicability, in particular for application to plants or plant parts or seed. The carrier, which may be solid or liquid, is generally inert and should be suitable for use in agriculture. Useful solid carriers include: for example ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates; useful solid carriers for granules include: for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, and also synthetic granules of inorganic and organic flours, and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; useful emulsifiers and/or foam-formers include: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and also protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POE ethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives, POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulfates, alkyl- or arylsulfonates and alkyl or aryl phosphates or the corresponding PO-ether adducts. Additionally suitable are oligo- or polymers, for example those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for example, (poly)alcohols or (poly)amines. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulfonic acids and also their adducts with formaldehyde.

The active ingredients can be converted to the customary formulations, such as solutions, emulsions, wet- table powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with active ingredi- ent, synthetic substances impregnated with active ingredient, fertilizers and also microencapsulations in polymeric substances.

The active ingredients can be applied as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concen- trates, natural products impregnated with active ingredient, synthetic substances impregnated with active ingredient, fertilizers and also microencapsulations in polymeric substances. Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading- on and the like. It is also possible to deploy the active ingredients by the ultra-low volume method or to inject the active ingredient preparation/the active ingredient itself into the soil. It is also possible to treat the seed of the plants.

The formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one customary extender, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, a water repellent, if appropriate siccatives and UV stabilizers and if appropriate dyes and pigments, antifoams, preservatives, secondary thickeners, stickers, gibberellins and also other pro- cessing auxiliaries. - oi -

The present invention includes not only formulations which are already ready for use and can be deployed with a suitable apparatus to the plant or the seed, but also commercial concentrates which have to be diluted with water prior to use.

The compounds of the formula (I) may be present as such or in their (commercial) formulations and in the use forms prepared from these formulations as a mixture with other (known) active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and/or semiochemicals.

The auxiliaries used may be those substances which are suitable for imparting particular properties to the composition itself or and/or to preparations derived therefrom (for example spray liquors, seed dressings), such as certain technical properties and/or also particular biological properties. Typical auxiliaries include: extenders, solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which may optionally also be substituted, etherified and/or esteri- fied), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the un- substituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethyl sulfoxide).

Liquefied gaseous extenders or carriers are understood to mean liquids which are gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, or else butane, propane, nitrogen and carbon dioxide.

In the formulations it is possible to use tackifiers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Further additives may be mineral and vegetable oils. If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Useful liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated ar- omatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.

Compositions comprising compounds of the formula (I) may additionally comprise further components, for example surfactants. Suitable surfactants are emulsifiers and/or foam formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, poly- condensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols, and derivatives of the compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignosulfite waste liquors and methylcellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and when application is effected in water. The proportion of surfactants is between 5 and 40 per cent by weight of the inventive composition.

It is possible to use dyes such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Further additives may be perfumes, mineral or vegetable, optionally modified oils, waxes and nutrients (in- eluding trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability.

If appropriate, other additional components may also be present, for example protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, stabilizers, sequestering agents, complex formers. In general, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

The formulations contain generally between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, more preferably between 0.5 and 90% of active ingredient, most preferably between 10 and 70 per cent by weight. The formulations described above can be used for controlling unwanted microorganisms, in which the compositions comprising compounds of the formula (I) are applied to the microorganisms and/or in their habitat.

Mixtures

Compounds of the formula (I) can be used as such or in formulations thereof and can be mixed with known fungicides, bactericides, acaricides, nematicides or insecticides, in order thus to broaden, for example, the activity spectrum or to prevent development of resistance. Useful mixing partners include, for example, known fungicides, insecticides, acaricides, nematicides or else bactericides (see also "The Pesticide Manual", 16th edition, November 2012, The British Crop Protection Council and the Royal Soc. of Chemistry).

A mixture with other known active ingredients, such as herbicides, or with fertilizers and growth regula- tors, safeners and/or semiochemicals, is also possible.

Seed treatment

The invention furthermore includes a method for treating seed.

A further aspect of the present invention relates in particular to seeds (dormant, primed, pregerminated or even with emerged roots and leaves) treated with at least one of the compounds of the formula (I). The in- ventive seeds are used in methods for protection of seeds and emerged plants from the seeds from phyto- pathogenic harmful fungi. In these methods, seed treated with at least one inventive active ingredient is used.

The compounds of the formula (I) are also suitable for the treatment of seeds and young seedlings. A large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seeds before sowing or after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even small damage may result in the death of the plant. Accordingly, there is great interest in protecting the seed and the germinating plant by using appropriate compositions.

It is also desirable to optimize the amount of the active ingredient used so as to provide the best possible protection for the seeds, the germinating plants and emerged seedlings from attack by phytopathogenic fungi, but without damaging the plants themselves by the active ingredient used. In particular, methods for the treatment of seed should also take into consideration the intrinsic phenotypes of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection compositions being employed. The present invention therefore also relates to a method for protecting seeds, germinating plants and emerged seedlings against attack by animal pests and/or phytopathogenic harmful microorganisms by treating the seeds with an inventive composition. The invention also relates to the use of the compositions according to the invention for treating seeds for protecting the seeds, the germinating plants and emerged seedlings against animal pests and/or phytopathogenic microorganisms. The invention further relates to seeds which have been treated with an inventive composition for protection from animal pests and/or phytopathogenic microorganisms. One of the advantages of the present invention is that the treatment of the seeds with these compositions not only protects the seed itself, but also the resulting plants after emergence, from animal pests and/or phytopathogenic harmful microorganisms. In this way, the immediate treatment of the crop at the time of sowing or shortly thereafter protect plants as well as seed treatment in prior to sowing. It is likewise con- sidered to be advantageous that the inventive active ingredients or compositions can be used especially also for transgenic seed, in which case the plant which grows from this seed is capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress. The treatment of such seeds with the inventive active ingredients or compositions, for example an insecticidal protein, can result in control of certain pests. Surprisingly, a further synergistic effect can be observed in this case, which additionally in- creases the effectiveness for protection against attack by pests, microorganisms, weeds or abiotic stress.

The compounds of the formula (I) are suitable for protection of seed of any plant variety which is used in agriculture, in the greenhouse, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particular significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.

As also described below, the treatment of transgenic seed with the inventive active ingredients or compositions is of particular significance. This refers to the seed of plants containing at least one heterologous gene which allows the expression of a polypeptide or protein, e.g. having insecticidal properties. These heterol- ogous genes in transgenic seeds may originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. These heterologous genes preferably originate from Bacillus sp., in which case the gene product is effective against the European corn borer and/or the Western corn rootworm. Particularly preferably, the heterologous genes originate from Bacillus thuringiensis. In the context of the present invention, the inventive composition is applied to seeds either alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, seeds can be treated at any time between harvest and some time after sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pre-germinated seeds, or seeds sown on nursery trays, tapes or paper.

When treating the seeds, it generally has to be ensured that the amount of the inventive composition ap- plied to the seed and/or the amount of further additives is selected such that the germination of the seed is n

- 67 - not impaired, or that the resulting plant is not damaged. This must be ensured particularly in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

The compounds of the formula (I) can be applied directly, i.e. without containing any other components and without having been diluted. In general, it is preferable to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art. The compounds of the formula (I) can be converted to the customary formulations relevant to on-seed applications, such as solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations. These formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibber- ellins, and also water.

Useful dyes which may be present in the seed dressing formulations usable in accordance with the inven- tion are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressing formulations usable in accordance with the invention are all substances which promote wetting and which are conventionally used for the formula- tion of active agrochemical ingredients. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonates.

Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations usable in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful nonionic dispersants include especially ethylene ox- ide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulfated derivatives thereof. Suitable anionic dispersants are especially lignosul- fonates, polyacrylic acid salts and arylsulfonate/formaldehyde condensates.

Antifoams which may be present in the seed dressing formulations usable in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference. Preservatives which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Examples include dichloro- phene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressing formulations usable in accordance with the invention are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Adhesives which may be present in the seed dressing formulations usable in accordance with the invention are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrroli- done, polyvinyl acetate, polyvinyl alcohol and tylose.

The formulations for on-seed applications usable in accordance with the invention can be used to treat a wide variety of different kinds of seed either directly or after prior dilution with water. For instance, the concentrates or the preparations obtainable therefrom by dilution with water can be used to dress the seed of cereals, such as wheat, barley, rye, oats, and triticale, and also seeds of maize, soybean, rice, oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a wide variety of different vegetable seeds. The formulations usable in accordance with the invention, or the dilute preparations thereof, can also be used for seeds of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.

For treatment of seeds with the formulations usable in accordance with the invention, or the preparations prepared therefrom by adding water, all mixing units usable customarily for on-seed applications are useful. Specifically, the procedure in on-seed applications is to place the seeds into a mixer, to add the particular desired amount of the formulations, either as such or after prior dilution with water, and to mix everything until all applied formulations are distributed homogeneously on the seeds. If appropriate, this is followed by a drying operation. The application rate of the formulations usable in accordance with the invention can be varied within a relatively wide range. It is guided by the particular content of the active ingredients in the formulations and by the seeds. The application rate of each single active ingredient is generally between 0.001 and 15 g per kilogram of seed, preferably between 0.01 and 5 g per kilogram of seed.

GMO As already mentioned above, it is possible to treat all plants and their parts in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if ap- propriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The terms "parts" or "parts of plants" or "plant parts" have been explained above. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention. Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloro- plastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A heterologous gene that is located in the ge- nome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means). Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold tem- perature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod ? or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability. Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses).

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics. Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, η or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as Tobacco plants, with altered post- translational protein modification patterns.

Application Rates

When using the compounds of the formula (I) as fungicides, the application rates can be varied within a relatively wide range, depending on the kind of application. The application rate of the inventive active ingredients is

• in the case of treatment of plant parts, for example leaves: from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rock- wool or perlite are used);

• in the case of seed treatment: from 0.1 to 200 g per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed;

• in the case of soil treatment: from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha.

These application rates are merely by way of example and are not limiting for the purposes of the invention.

The invention is illustrated by the examples below. However, the invention is not limited to the examples.

Examples

List of abbreviations used in the context of the present invention cone. concentrated, meaning a saturated aqueous solution

DBU 2,3,4,6,7,8,9,10-octahydropyrimido[l,2-a]azepine (CAS RN 6674-22-2)

DCM dichloromethane

DIPEA N-Ethyl-N,N-diisopropylamine

DMAP N,N-dimetyl-4-aminopyridine

DMF N,N-dimethylformamide

DMPU 1 ,3 -dimethyltetrahydropyrimidin-2( 1 H)-one

DMSO dimethylsulfoxide - 7 - d 6 -OMSO hexadeuterated DMSO

HATU N- [(dimethylamino)(3H- [ 1 ,2,3]triazolo [4,5-b]pyridin-3 -yloxy)methylidene] -N- methylmethanaminium hexafluorophosphate (CAS RN 148893-10-1)

NMR nuclear magnetic resonance spectroscopy

NMO N-methylmorpholine

TBTU N- [( 1 H-benzotriazol- 1 -yloxy)(dimethylamino)methylidene] -N-methylmethanaminium tetra- fluoroborate (CAS RN 125700-67-6)

TEA triethylamine

THF tetrahydrofuran

TFA trifluoroacetic acid

LogP values

Measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: [a] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

M LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

[ c] LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

Calibration was done with straight-chain alkan-2-ones (with 3 to 16 carbon atoms) with known LogP values (measurement of LogP values using retention times with linear interpolation between successive alka- nones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak val- ues of the chromatographic signals.

NMR-Peak lists

IH-NMR data of selected examples are written in form of IH-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value - signal intensity pairs are semicolons as delimiters. The peak list of an example has therefore the form:

δι (intensity!); δ2 (intensity2); ; δ; (intensity;); ; δ η (intensity^

Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of - 7 - the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetrame- thylsilane peak can occur but not necessarily.

The 1 H-NMR peak lists are similar to classical 1 H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

Additionally they can show like classical 'H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities. To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D6 and the peak of water are shown in our 1 H-NMR peak lists and have usually on average a high intensity .

The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90 %). Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via "side-products-fingerprints".

An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD- simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1 H-NMR interpretation.

Further details of NMR-data description with peak lists you find in the publication "Citation of NMR Peaklist Data within Patent Applications" of the Research Disclosure Database Number 564025.

Synthesis Examples

Synthesis of N-[4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-l]c yclopentanecarboxamide (Example compound 1)

?

4-(2-Chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-ami ne (100 mg, 0.41 mmol) was dissolved in THF (1.0 mL) in a microwave process vial. Cyclopentane carboxylic acid (57 mg, 0.50 mmol), pro- panephosphonic anhydride (0.80 g, 1.25 mmol) and triethylamine (100 mg, 1.0 mmol) were added. The vial was crimp-capped and the mixture was heated to 150 °C for 10 min in a single mode microwave device. After cooling, cone, ammonium chloride was added, the solution was extracted with ethyl acetate, the organic extract was dried, evaporated and the residue was purified by silica gel chromatography (cyclohexane- ethyl acetate gradient). 73 mg of Example compound 1 were obtained (51% of theory).

Synthesis of 2-chloro-N-[4-(2-chloro-4-fluorophenyl)-l ,3-dimethyl-lH-pyrazol-5-yl]-4- fluorobenzenesulfonamide (Example compound 16)

4-(2-Chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-ami ne (100 mg, 0.41 mmol) was dissolved in pyridine (0.4 mL), (2-chloro-4-fluorophenyl)sulfonic chloride (105 mg, 0.45 mmol) was added and the mixture was left stirring for 16 h. The solvent was then distilled and the residue was purified by silica gel chromatography (cyclohexane- ethyl acetate gradient). 97 mg of Example compound 16 were obtained (53% of theory).

Synthesis of 5-[(2-chloro-4-fluorobenzyl)oxy]-4-(2-chloro-4-fluorophenyl) -l,3-dimethyl-lH-pyrazole (Example compound 18)

4-(2-Chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-ol (290 mg, 1.20 mmol) was dissolved in DMF (2.0 mL) and sodium hydride (58 mg, 60%> in paraffin, 1.44 mmol) was added. The mixture was stirred at room temperature for 5 min, then l-(bromomethyl)-2-chloro-4-fluorobenzene (296 mg, 1.32 mmol) was added and the mixture was stirred at 50 °C for 16 h. Then the solvent was distilled in vacuo and the ?5 residue was partitioned between cone, ammonium chloride and ethyl acetate. The organic phase was dried over sodium sulfate, evaporated and the residue was purified by silica gel chromatography (cyclo- hexane-ethyl acetate gradient). The Example compound 18 (134 mg, 29% of theory) was obtained as a light yellow resin. Preparation Examples

According to the described methodologies, the following compounds of the formula (I) according to the present invention in which R = methyl and Q 1 = 2-chloro-4-fluorophenyl were synthesised (Example compounds):

Example

X Y Q 2 LogP

compound

1 NH c=o cyclopentyl 2.67 [a] ; 2.61 M

2 NH c=o tert-butyl 2.68 [a] ; 2.56 M

3 NH c=o isopropyl 2.22 [a] ; 2.19 M

4 NH c=o 2-methoxyphenyl 2.90 [a] ; 2.84 M

5 NH c=o cyclopropyl 2.07 [a] ; 2.05 M

6 NH c=o 5-chloro-2-thienyl 3.10 [a] ; 3.03 M

7 NH c=o 2,4-difluorophenyl 2.83 [a] ; 2.78 M

8 NH c=o methyl 1.72 [a] ; 1.67 M

9 NH c=o 2-chloro-4-fluorophenyl 2.86 [a] ; 2.79 M

10 NH c=o 2,6-difluorophenyl 2.58 [a] ; 2.53 M

11 NH c=o 2,4-dichlorophenyl 3.23 [a] ; 3.15 M

12 NH c=o 2-(trimethylsilyl)ethyl 3.46 [a] ; 3.38 M

13 NH c=o 2-chloro-6-fluorophenyl 2.74 [a] ; 2.68 M

14 NH c=o 3 -(trifluoromethyl)phenyl 3.27 [a] ; 3.20 M

15 NH so 2 ethyl 2.12 [a] ; 1.54 M

16 NH so 2 2-chloro-4-fluorophenyl 3.00 [a] ; 1.53 M

17 O CH 2 2-chloro-5-fluorophenyl 4.19 [a] ; 4.03 M

18 O CH 2 2-chloro-4-fluorophenyl 4.23 [a] ; 4.11 M

19 0 CH 2 4-fluorophenyl 3.79 [a] ; 3.75 M ; 3.80 [c]

20 0 CH 2 4-chlorophenyl 4.22 [a] ; 4.16 M

21 0 CH 2 3-chlorophenyl 4.19 [a] ; 4.14 M

22 0 CH 2 2,4,6-trifluorophenyl 3.87 [a] ; 3.83 M

23 0 CH 2 2,6-dichlorophenyl 4.39 [a] ; 4.34 M ; 4.40 [c]

24 0 CH 2 2,6-difluorophenyl 3.76 [a] ; 3.71 M ; 3.80 [c] -7 -

NMR peak lists for active ingredients according to formula (I) δ = 9.862 (3.3); 7.522 (1.7); 7.516 (1.7); 7.500 (1.6); 7.494 (1.6); 7.278 (0.6); 7.272 (0.5); 7.257 (1.7); 7.251 (1.7); 7.235 (3.0); 7.218 (2.4); 7.196 (0.6); 5.752 (3.5); 4.038 (0.5); 4.020 (0.5); 3.682 (0.4); 3.546 (16.0); 3.325 (18.7); 2.524 (0.5); 2.511 (1 1.6); 2.507 (23.5); 2.502 (31.3); 2.498 (23.2); 2.494 (1 1.6); 2.032 (0.4); 2.005 (16.0); 1.988 (2.4); 1.718 (0.7); 1.711 (0.8); 1.699 (1.3); 1.692 (0.7); 1.687 (0.8); 1.680 (0.7); 1.668 (0.4); 1.194 (0.6); 1.176 (1.2); 1.158 (0.6); 0.784 (0.4); 0.771 (1.3); 0.764 (3.2); 0.744 (4.6); 0.740 (4.8); 0.729 (3.6); 0.721 (1.4); 0.008 (0.8); 0.000 (21.3); -0.009 (0.9)

Example 6: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.280 (2.1); 7.771 (1.3); 7.761 (1.3); 7.514 (1.5); 7.508 (1.6); 7.492 (1.6); 7.485 (1.6); 7.300 (0.5); 7.279 (1.5); 7.263 (1.5); 7.258 (1.6); 7.251 (1.3); 7.243 (2.6); 7.237 (2.3); 7.232 (3.2); 7.215 (0.6); 7.209 (0.5); 5.758 (5.9); 4.039 (0.5); 4.021 (0.5); 3.630 (16.0); 3.331 (9.3); 2.512 (7.2); 2.508 (14.7); 2.503 (19.5); 2.499 (14.4); 2.495 (7.2); 2.051 (15.5); 1.990 (1.9); 1.235 (0.6); 1.193 (0.5); 1.176 (1.0); 1.158 (0.5); 0.008 (0.4); 0.000 (10.0); -0.008 (0.4)

Example 7: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.193 (3.5); 7.703 (0.7); 7.682 (1.5); 7.665 (1.5); 7.644 (0.8); 7.524 (1.6); 7.518 (1.7); 7.502 (1.7); 7.495 (1.7); 7.427 (0.8); 7.421 (0.9); 7.397 (1.4); 7.377 (0.8); 7.371 (0.9); 7.334 (1.1); 7.318 (1.4); 7.313 (2.2); 7.297 (2.0); 7.271 (1.2); 7.265 (1.2); 7.250 (1.8); 7.244 (1.7); 7.229 (1.4); 7.223 (0.9); 7.212 (1.5); 7.207 (1.5); 7.191 (0.8); 7.185 (0.7); 5.758 (2.6); 3.662 (16.0); 3.330 (11.5); 2.511 (9.4); 2.507 (18.9); 2.503 (25.0); 2.498 (18.8); 2.055 (15.4); 1.990 (0.9); 1.175 (0.5); 0.000 (5.7)

Example 8: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 9.652 (2.5); 7.522 (1.2); 7.517 (1.2); 7.499 (1.1); 7.495 (1.2); 7.257 (1.5); 7.251 (1.9); 7.248 (2.2); 7.237 (1.7); 7.231 (3.3); 5.757 (0.7); 3.660 (0.4); 3.561 (14.5); 3.330 (8.6); 2.520 (0.5); 2.51 1 (6.9); 2.507 (14.3); 2.502 (19.0); 2.498 (13.7); 2.493 (6.6); 2.024 (0.4); 2.003 (14.7); 1.989 (1.1); 1.943 (16.0); 1.909 (0.5); 1.551 (0.4); 1.236 (0.4); 1.175 (0.5); 0.008 (0.3); 0.000 (10.2); -0.009 (0.3)

Example 9: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.352 (3.4); 7.562 (1.7); 7.556 (1.8); 7.540 (2.6); 7.533 (2.0); 7.526 (2.4); 7.520 (2.7); 7.505 (3.0); 7.499 (1.8); 7.356 (1.1); 7.350 (2.0); 7.335 (2.9); 7.329 (3.8); 7.313 (2.8); 7.308 (1.0); 7.292 (1.3); 7.286 (1.2); 7.271 (1.8); 7.265 (1.6); 7.250 (0.7); 7.244 (0.6); 5.752 (4.3); 4.038 (0.5); 4.021 (0.5); 3.706 (16.0); 3.326 (15.7); 2.511 (10.0); 2.507 (20.9); 2.502 (28.1); 2.498 (20.4); 2.493 (9.9); 2.052 (15.3); 1.989 (2.4); 1.236 (0.7); 1.194 (0.6); 1.176 (1.2); 1.158 (0.6); 0.000 (9.0)

Example 10: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.615 (3.3); 7.602 (0.4); 7.585 (0.8); 7.581 (0.8); 7.569 (0.6); 7.564 (1.5); 7.547 (0.8); 7.543 (1.0); 7.534 (1.7); 7.528 (1.9); 7.512 (1.7); 7.506 (1.7); 7.322 (0.8); 7.306 (1.0); 7.301 (2.2); 7.285 (2.1); 7.278 (1.4); 7.271 (1.3); 7.257 (1.7); 7.250 (1.6); 7.236 (0.6); 7.229 (1.0); 7.222 (2.6); 7.201 (3.7); 7.181 (2.3);

7.175 (0.6); 5.752 (3.7); 3.722 (0.9); 3.674 (16.0); 3.326 (9.3); 2.524 (0.5); 2.51 1 (11.1); 2.507 (22.9); 2.502 (30.9); 2.498 (23.2); 2.493 (11.9); 2.055 (15.6); 1.989 (1.3); 1.878 (0.9); 1.398 (0.5); 1.194 (0.4);

1.176 (0.7); 1.158 (0.3); 0.008 (1.0); 0.000 (30.6); -0.009 (1.5) - 7 -

Example 1 1 : ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.398 (3.6); 7.731 (3.6); 7.726 (3.8); 7.557 (1.6); 7.552 (1.5); 7.536 (2.9); 7.531 (4.4); 7.525 (1.8); 7.509 (1.8); 7.502 (1.8); 7.488 (4.7); 7.468 (2.6); 7.348 (1.0); 7.332 (1.2); 7.326 (2.2); 7.310 (2.1); 7.294

(1.3) ; 7.287 (1.2); 7.273 (1.8); 7.266 (1.7); 7.251 (0.7); 7.245 (0.6); 5.755 (6.7); 4.038 (0.5); 4.020 (0.5); 3.784 (0.3); 3.706 (16.0); 3.325 (12.1); 2.524 (0.4); 2.520 (0.7); 2.51 1 (10.3); 2.507 (21.6); 2.502 (29.0); 2.497 (21.0); 2.493 (10.1); 2.050 (15.3); 1.989 (2.4); 1.398 (0.3); 1.193 (0.6); 1.176 (1.3); 1.158 (0.6); 0.008 (0.7); 0.000 (21.6); -0.009 (0.7)

Example 12: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 9.558 (3.5); 7.509 (1.7); 7.487 (1.9); 7.238 (3.9); 7.223 (4.0); 7.220 (3.9); 5.757 (1.4); 3.551 (16.0); 3.508 (0.7); 3.505 (0.7); 2.507 (12.3); 2.503 (15.9); 2.498 (11.8); 2.205 (2.5); 2.184 (2.5); 2.163 (2.7); 2.005 (15.5); 1.990 (0.7); 1.236 (0.4); 0.740 (1.4); 0.736 (1.4); 0.723 (1.9); 0.712 (2.0); 0.699 (1.4); 0.694 (1.2); 0.000 (2.5); -0.015 (1.1); -0.043 (52.5); -0.180 (0.6); -0.193 (0.5)

Example 13 : ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.616 (2.8); 7.548 (0.7); 7.528 (2.3); 7.523 (1.9); 7.512 (1.8); 7.507 (2.8); 7.501 (1.7); 7.491 (1.1); 7.414 (0.5); 7.402 (2.6); 7.394 (0.5); 7.382 (1.8); 7.356 (1.3); 7.335 (2.6); 7.320 (1.2); 7.314 (2.7); 7.298 (2.0); 7.285 (1.2); 7.278 (1.1); 7.264 (1.7); 7.257 (1.5); 7.242 (0.6); 7.236 (0.5); 5.753 (4.0); 3.743 (0.4); 3.707 (16.0); 3.325 (9.4); 2.525 (0.7); 2.520 (1.0); 2.511 (16.6); 2.507 (34.5); 2.502 (46.1); 2.498 (33.2); 2.493 (15.8); 2.049 (15.5); 1.989 (1.0); 1.176 (0.5); 0.008 (1.0); 0.000 (33.2); -0.009 (1.1)

Example 14: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.430 (3.6); 8.215 (2.9); 8.192 (1.6); 8.172 (1.8); 7.986 (1.5); 7.967 (1.8); 7.784 (1.2); 7.765 (2.1); 7.745 (1.0); 7.499 (1.6); 7.492 (1.7); 7.476 (1.6); 7.470 (1.6); 7.324 (1.2); 7.308 (1.4); 7.303 (2.0); 7.287 (1.9); 7.241 (1.2); 7.235 (1.1); 7.220 (1.8); 7.214 (1.7); 7.199 (0.7); 7.192 (0.7); 5.753 (4.7); 4.058 (0.3); 4.040 (1.0); 4.022 (1.0); 4.004 (0.4); 3.661 (16.0); 3.329 (12.0); 2.527 (0.4); 2.514 (10.2); 2.509 (21.1); 2.505 (28.1); 2.500 (20.3); 2.496 (9.7); 2.071 (15.2); 1.990 (4.5); 1.236 (0.7); 1.195 (1.2); 1.177 (2.4); 1.160 (1.2); 0.008 (1.0); 0.000 (31.3); -0.009 (1.0)

Example 15: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 9.762 (3.4); 7.590 (1.6); 7.583 (1.6); 7.568 (1.6); 7.561 (1.6); 7.409 (1.1); 7.393 (1.3); 7.388 (2.0); 7.372 (1.9); 7.338 (1.1); 7.331 (1.1); 7.317 (1.7); 7.310 (1.6); 7.295 (0.7); 7.289 (0.6); 5.758 (1.6); 3.729 (16.0); 3.329 (10.3); 2.759 (0.8); 2.741 (1.2); 2.723 (1.4); 2.705 (1.1); 2.686 (0.3); 2.555 (1.1); 2.537

(1.4) ; 2.519 (1.5); 2.512 (6.0); 2.507 (12.3); 2.503 (16.7); 2.498 (12.2); 2.494 (6.0); 1.992 (15.9); 0.764 (3.6); 0.746 (7.8); 0.728 (3.4); 0.000 (1.0)

Example 16: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 10.587 (2.5); 7.699 (1.4); 7.684 (1.5); 7.677 (1.6); 7.662 (1.5); 7.246 (1.3); 7.240 (1.8); 7.224 (1.5); 7.218 (2.1); 7.199 (1.6); 7.193 (1.1); 7.178 (1.0); 7.172 (0.7); 7.142 (1.2); 7.137 (1.3); 7.120 (1.3); 7.115 (1.4); 7.067 (2.7); 7.061 (1.5); 7.052 (2.0); 7.047 (1.8); 7.041 (1.4); 5.758 (0.4); 3.761 (16.0); 3.332 (10.7); 2.512 (7.3); 2.508 (15.2); 2.503 (20.4); 2.499 (15.0); 2.494 (7.5); 1.893 (15.9); 0.000 (3.9) -7 -

- -

- - δ = 7.532 (1.6); 7.525 (1.6); 7.510 (1.6); 7.503 (1.6); 7.418 (0.3); 7.413 (0.4); 7.404 (0.4); 7.399 (0.8); 7.397 (0.7); 7.383 (0.7); 7.379 (1.0); 7.374 (0.6); 7.365 (0.5); 7.360 (0.6); 7.356 (1.3); 7.340 (1.3); 7.334 (1.9); 7.318 (1.8); 7.275 (0.6); 7.270 (0.6); 7.258 (1.9); 7.251 (2.3); 7.237 (2.5); 7.230 (1.9); 7.216 (0.8); 7.209 (0.7); 7.171 (1.1); 7.164 (1.3); 7.161 (1.2); 7.145 (3.2); 7.125 (1.9); 5.757 (6.6); 4.827 (6.4); 3.509 (15.9); 3.325 (14.6); 2.525 (0.5); 2.520 (0.7); 2.512 (1 1.4); 2.507 (23.8); 2.503 (31.9); 2.498 (23.1); 2.494 (11.1); 1.916 (16.0); 0.146 (0.4); 0.008 (2.8); 0.000 (76.1); -0.009 (3.0); -0.150 (0.4)

Example 30: 'H-NMR (400.0 MHz, d 6 -OMSO):

δ = 7.513 (1.6); 7.506 (1.6); 7.491 (1.6); 7.484 (1.6); 7.331 (1.7); 7.315 (1.9); 7.310 (3.2); 7.294 (3.0); 7.272 (0.7); 7.248 (1.1); 7.242 (1.0); 7.227 (1.7); 7.221 (1.6); 7.206 (0.8); 7.200 (1.1); 7.194 (0.8); 7.175 (1.0); 7.169 (1.0); 7.151 (0.7); 7.145 (0.7); 7.039 (0.6); 7.033 (0.5); 7.020 (1.0); 7.018 (1.1); 7.014 (1.0); 7.012 (1.0); 6.999 (0.5); 6.997 (0.5); 6.991 (0.5); 4.810 (6.3); 3.528 (16.0); 3.326 (30.8); 2.525 (0.6); 2.512 (13.5); 2.507 (27.6); 2.503 (36.6); 2.498 (26.7); 2.494 (13.0); 2.027 (0.3); 1.916 (16.0); 0.146 (0.4); 0.008 (3.0); 0.000 (76.8); -0.009 (3.0); -0.150 (0.4)

Example 31 : 'H-NMR (400.0 MHz, d 6 -OMSO):

δ = 7.314 (1.4); 7.309 (1.3); 7.292 (1.5); 7.286 (1.4); 7.279 (1.0); 7.266 (1.3); 7.256 (1.4); 7.243 (1.1); 7.071 (0.4); 7.062 (1.6); 7.053 (1.3); 7.046 (1.3); 7.042 (1.4); 7.035 (1.3); 7.026 (1.6); 7.019 (0.6); 6.998 (2.3); 6.993 (1.9); 6.987 (1.6); 6.981 (2.3); 6.973 (1.7); 6.967 (1.5); 6.945 (0.3); 5.920 (0.7); 5.903 (1.6); 5.887 (0.8); 4.039 (0.6); 4.021 (0.5); 3.998 (1.5); 3.980 (2.6); 3.963 (1.5); 3.632 (15.8); 3.329 (12.4); 2.512 (6.6); 2.508 (13.2); 2.503 (17.3); 2.499 (12.6); 2.494 (6.1); 1.989 (1.6); 1.910 (2.4); 1.740 (16.0); 1.397 (0.5); 1.193 (0.4); 1.176 (0.9); 1.158 (0.4); 0.008 (0.7); 0.000 (19.4); -0.009 (0.7)

Example 32: ¾-NMR (400.0 MHz, d 6 -OMSO):

δ = 7.419 (1.1); 7.415 (1.6); 7.396 (1.2); 7.393 (1.8); 7.1 17 (3.3); 7.1 14 (3.5); 7.099 (3.9); 7.095 (3.3); 7.028 (1.0); 7.022 (0.5); 7.006 (4.2); 6.989 (3.8); 6.984 (4.9); 6.974 (3.9); 6.967 (1.4); 6.958 (0.4); 6.952 (0.6); 5.758 (0.7); 5.722 (0.8); 5.705 (1.6); 5.689 (0.8); 3.843 (2.7); 3.826 (2.6); 3.556 (15.8); 3.335 (10.9); 2.508 (13.7); 2.504 (17.2); 2.499 (12.1); 1.964 (0.9); 1.91 1 (0.5); 1.770 (16.0); 0.000 (1.0)

Biological examples

Biological Example 1 : in vivo preventive test on Septoria tritici (leaf spot on wheat)

Solvent: 5% by volume of DMSO

10% by volume of Acetone

Emulsifier: 1 μΐ of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ® 80 and then diluted in water to the desired concentration. The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18°C and at 100% relative hu- midity and then for 21 days at 20°C and at 90%> relative humidity.

The test is evaluated 24 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: Example compounds 1 ; 2; 3; 4; 5; 6; 7; 8; 9; 10; 11 ; 12; 15; 16; 17; 18; 19; 20; 21 ; 26; 28

Biological Example 2: in vivo preventive test on Sphaerotheca fuUginea (powdery mildew on cucurbits)

Solvent: 5% by volume of DMSO

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ® 80 and then diluted in water to the desired concentration.

The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ® 80. After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuUginea spores. The contaminated gherkin plants are incubated for 72 hours at 18°C and at 100% relative humidity and then for 12 days at 20°C and at 70-80% relative humidity.

The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed. In this test the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: Example compounds 1 ; 2; 3; 4; 5; 6; 15; 17; 18; 19; 21; 26; 30; 31; 32

Biological Example 3: in vivo preventive test on Puccinia recondita (brown rust on wheat)

Solvent: 5% by volume of Dimethyl sulfoxide

10%) by volume of Acetone

Emulsifier: 1 μΐ of Tween ® 80 per mg of active ingredient - -

The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/ /Tween ® 80 and then diluted in water to the desired concentration.

The young plants of wheat are treated by spraying the active ingredient prepared as described above. Con- trol plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/ Tween ® 80.

After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20°C and at 100% relative humidity and then for 10 days at 20°C and at 70-80%> relative humidity.

The test is evaluated 11 days after the inoculation. 0%> means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

In this test, the following compounds according to the invention showed efficacy of at least 70% at a concentration of 500 ppm of active ingredient: Example compounds 17; 18; 19

Biological Example 4 - Comparative biological data

The following compounds (V-1), (V-2) and (V-3) not according to formula (I) of the present invention were each tested regarding their efficacy in controlling Puccinia recondita (brown rust) on wheat, Septoria tritici (leaf spot) on wheat, and Sphaerotheca fuliginea (powdery mildew) on cucurbits as described in the above Biological Examples 1, 2 and 3, respectively.

(V-1) (V-2) - -

Compounds (V-1) and (V-2) showed 0% efficacy against the three mentioned fungi at a concentration of 500 ppm of active ingredient. At a concentration of 500 ppm of active ingredient compound (V-3) showed 0% efficacy in controlling Puccinia recondita (brown rust) on wheat and Sphaerotheca fuliginea (powdery mildew) on cucurbits, and 25% efficacy in controlling Septoria tritici (leaf spot) on wheat.




 
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