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US 11,440,910 B2Granted
Pesticidally active heterocyclic derivatives with sulfur containing substituents
AssigneeSyngenta Participations AG
InventorsSebastian Rendler, Andrew Edmunds, Pierre Joseph Marcel Jung, Michel Muehlebach, Girish Rawal, Indira Sen, Vikas Sikervar
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Abstract
Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, can be used as insecticides and can be prepared in a manner known per se.
Claims28
A compound of formula I,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
- G1 is N or CH;
- X1 is O, S or NR3;
- wherein R3 is hydrogen or C1-C4alkyl;
- R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is chlorine, bromine, iodine, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.
9 more elements
A compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, of formula I,
- wherein A is N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
- G1 is N or CH;
- X1 is O, S or NR3;
- wherein R3 is hydrogen or C1-C4alkyl;
- R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl.
7 more elements
A compound of formula IX,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl;
- G1 is N or CH;
- R3 is hydrogen or C1-C4alkyl;
- R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxyC1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- or a regioisomer thereof, or an isomeric mixture thereof;
- or
- a compound of formula XI,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- or
- a compound of formula XII,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- or
- a compound of formula XIII,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl;
- R7 is hydrogen, halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- RLG is C1-C4alkyl and wherein the compound is not
- or
- a compound of formula XVI,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl;
- R11 is C1-C4alkyl;
- and
- RLG is C1-C4alkyl.
46 more elements
A compound of formula I,
- wherein
- A is CH or N;
- X is S, SO or SO2;
- R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;
- G1 is N or CH;
- X1 is O, S or NR3;
- wherein R3 is hydrogen or C1-C4alkyl;
- R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;
- R7 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and
- R8 is halogen, cyano, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4alkylsulfanyl, C1-C4alkylsulfanyl-C1-C4alkyl, C1-C4alkylsulfinyl-C1-C4alkyl, C1-C4alkylsulfonyl-C1-C4alkyl or C1-C4alkyloxycarbonyl;
- and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.
9 more elements
A compound selected from
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanedinitrile;
- 2-[5-ethylsulfonyl-6-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]-3-pyridyl]-2-methyl-propanenitrile;
- 2-ethyl-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]butanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]butanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanenitrile;
- 2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanedinitrile;
- 2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanedinitrile;
- ethyl 2-cyano-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanoate;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-3-methyl-butanenitrile;
- 2-[3-ethylsulfanyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]-2-methyl-propanenitrile;
- 2-[3-ethylsulfonyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]-2-methyl-propanenitrile;
- 2-[3-ethylsulfanyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]propanenitrile;
- 2-[3-ethylsulfonyl-4-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]phenyl]propanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2,2-difluoro-acetonitrile;
- 2-[3-ethylsulfanyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-2-methyl-propanenitrile;
- 2-[3-ethylsulfonyl-4-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]phenyl]-2-methyl-propanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-fluoro-propanenitrile;
- 2-[6-(6-bromo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-5-ethylsulfonyl-3-pyridyl]-2-methyl-propanenitrile;
- 2-[5-ethylsulfonyl-6-[3-methyl-6-(1,1,2,2,2-pentafluoroethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
- ethyl 2-cyano-2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]propanoate;
- 2-[5-ethylsulfonyl-6-(6-iodo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-3-pyridyl]-2-methyl-propanenitrile;
- 2-[6-(6-bromo-3-methyl-imidazo[4,5-c]pyridin-2-yl)-5-ethylsulfanyl-3-pyridyl]-2-methyl-propanenitrile;
- 2-[5-ethylsulfanyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]-2-methyl-propanenitrile;
- ethyl 2-cyano-2-[5-ethylsulfonyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]-3-pyridyl]acetate;
- and
- 2-[5-ethylsulfanyl-6-[7-methyl-3-(trifluoromethyl)imidazo[4,5-c]pyridazin-6-yl]-3-pyridyl]-2-methyl-propanenitrile.
24 more elements
Dependencies are inferred from the claim text.