4-membered ring carboxamides used as nematicides

Patent metadata

Field	Value
Publication number	US-2016157485-A1
Application number	US-201414903169-A
Country	US
Kind code	A1
Filing date	Jul 1, 2014
Priority date	Jul 8, 2013
Publication date	Jun 9, 2016
Grant date	—

Abstract

Compounds of the formula (I), in which the substituents are as defined in claim 1 , are suitable for use as nematicides.

First claim

1 . A compound of the formula I

wherein
Y represents O or CH2;
A represents phenyl or a 5- or 6-membered heterocyclic ring containing 1 to 3 heteroatoms independently selected from oxygen, nitrogen and sulphur, wherein the phenyl is optionally substituted by one or more R3 and the heteroaromatic ring is optionally substituted by one or more R4;
B represents phenyl optionally substituted by one or more R5;
R1 represents hydrogen, hydroxy, C1-C4 alkoxy, C1-C4 haloalkoxy; C1-C4 alkyl, cyano, C1-C4 haloalkyl or halogen;
R2 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxycarbonyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-cyanoalkyl or C3-C6-cycloalkylcarbonyl, C3-C6-cycloalkoxycarbonyl or benzyl;
each R3 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-haloalkylthio;
each R4 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-haloalkylthio;
each R5 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylsulfanyl, C1-C4-haloalkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C2-C6-haloalkenyl, C2-C6 haloalkynyl, 5- or 6-membered heterocycle optionally substituted by one or more substituents R6 or C3-C6-cycloalkyl optionally substituted by one or more substituents R6
each R6 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkyloxycarbonyl;
and tautomers/isomers/enantiomers/salts and N-oxides of these compounds.

2 . A compound according to claim 1 wherein R1 and R2 are each hydrogen.

3 . A compound according to claim 1 wherein
Y represents O or CH2;
A represents phenyl, pyridyl, pyrimidyl, pyrazinyl, pyrazolyl, thienyl or furyl, wherein the phenyl is optionally substituted by one or more R3 and each heteroaromatic ring is optionally substituted by one or more R4;
B represents phenyl optionally substituted by one or more R5;
R1 represents hydrogen;
R2 represents hydrogen;
each R3 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-haloalkylthio;
each R4 independently of one another represent halogen, C1-C4-alkyl or C1-C4-haloalkyl;
each R5 independently of one another represent halogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy, C2-C6-haloalkenyl, 5- or 6-membered heterocycle or C3-C6-cycloalkyl wherein the heterocycle and the cycloalkyl are each optionally substituted by one or more substituents R6;
each R6 independently of one another represent halogen, C1-C4-alkyl or C1-C4-haloalkyl.

4 . A compound of formula I according to claim 1 wherein
Y represents O or CH2;
A represents phenyl, pyridyl, pyrimidyl, pyrazinyl, pyrazolyl, thienyl or furyl, wherein the phenyl is optionally substituted by one or more R3 and each heteroaromatic ring is optionally substituted by one or more R4;
B represents phenyl optionally substituted by one or more R5;
R1 represents hydrogen;
R2 represents hydrogen
each R3 independently of one another represent halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-haloalkylthio;
each R4 independently of one another represent halogen, C1-C4-alkyl or C1-C4-haloalkyl;
each R5 independently of one another represent halogen, cyano, C1-C4-haloalkyl, C1-C4-haloalkoxy or C3-C6-cycloalkyl optionally substituted by one or more substituents R6;
each R6 independently of one another represent selected from halogen, C1-C4-alkyl or C1-C4-haloalkyl.

5 . A compound of formula I according to claim 1 wherein
Y represents CH2;
A represents phenyl, pyridyl, pyrazinyl, furyl or pyrazolyl wherein the phenyl is optionally substituted by one or more R3 and each heteroaromatic ring is optionally substituted by one or more R4;
B represents phenyl optionally substituted by one or more R5;
R1 represents hydrogen;
R2 represents hydrogen;
each R3 independently of one another represent halogen or trifluoromethyl;
each R4 independently of one another represent halogen, C1-C4-alkyl or C1-C4-haloalkyl;
each R5 independently of one another represent halogen or trifluoromethyl.

6 . A compound of formula I according to claim 1 wherein
Y represents CH2;
A represents phenyl, 2-pyridyl, 3-pyridyl, 2-pyrazinyl, 2-furyl, 3-furyl or 4-pyrazolyl wherein the phenyl is optionally substituted by one or more R3 and each heteroaromatic ring is optionally substituted by one to three or more R4;
B represents phenyl optionally substituted by one or two R5;
R1 represents hydrogen;
R2 represents hydrogen;
each R3 independently of one another represent halogen or trifluoromethyl;
each R4 independently of one another represent halogen, C1-C2-alkyl or C1-C2-haloalkyl;
each R5 independently of one another represent halogen or trifluoromethyl.

7 . A compound of formula (I) according to claim 1 wherein
Y represents CH2;
A represents phenyl, 2-pyrazinyl, 2-pyridyl, 3-pyridyl, 2-furyl, or 3-fury) wherein the phenyl is optionally substituted by one R3 and the heteroaromatic rings are optionally substituted by one R4;
B represents R8 or R9;
R1 represents hydrogen;
R2 represents hydrogen;
R3 represents halogen, methyl, difluoromethyl or trifluoromethyl;
R4 represents chloro, bromo, methyl, difluoromethyl or trifluoromethyl;
R8 represents

R9 represents

R10 represents fluoro, chloro, bromo, difluoromethyl, trifluoromethyl, difluoromethoxy or trifluoromethoxy;
R11 represents fluoro, chloro or bromo;
R12 represents fluoro, chloro, bromo or trifluoromethyl.

8 . A compound of formula (I) according to claim 1 wherein
Y represents CH2;
A represents phenyl, 2-pyrazinyl, 2-pyridyl, 3-pyridyl, 2-furyl or 3-furyl wherein the phenyl is optionally substituted by one R3 and the heteroaromatic rings are optionally substituted by one R4;
B represents R8 or R9;
R1 represents hydrogen;
R2 represents hydrogen;
R3 represents trifluoromethyl;
R4 represents chloro, difluoromethyl or trifluoromethyl;
R8 represents

R9 represents

R10 represents chloro;
R11 represents fluoro or chloro;
R12 represents chloro, fluoro or trifluoromethyl.

9 . A pesticidal composition, which, in addition to comprising formulation adjuvants, comprises a nematicidal effective amount of a compound of the formula I according to claim 1 .

10 . A composition according to claim 9 , which further comprises one or more insecticidally, acaricidally, nematicidally and/or fungicidally active agents.

11 . A method of protecting crops of useful plants against damages caused by nematode pests, which comprises treating the plants or the locus thereof with a composition according to claim 9 .

12 . A method of protecting plant propagation material against damages caused by nematode pests, which comprises treating this material with a composition according to claim 9 .

13 . A metho

Assignees

• Syngenta Participations Ag

Inventors

• O-Sullivan Anthony Cornelius
• Mondiere Regis Jean Georges
• Loiseleur Olivier
• Smejkal Tomas
• Luksch Torsten
• Jeanguenat Andre
• Dumeunier Raphael
• Godineau Edouard
• Pittema Thomas

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07B2200/07

  Optical isomers · CPC title

• C07D231/14

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title