Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-11440910-B2
Application number	US-201816487278-A
Country	US
Kind code	B2
Filing date	Feb 16, 2018
Priority date	Feb 21, 2017
Publication date	Sep 13, 2022
Grant date	Sep 13, 2022

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.

First claim

What is claimed is:

1. A compound of formula I,

wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl;
G 1 is N or CH;
X 1 is O, S or NR 3 ; wherein R 3 is hydrogen or C 1 -C 4 alkyl;
R 2 is halogen, C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl or C 1 -C 6 haloalkoxy;
R 7 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and
R 8 is chlorine, bromine, iodine, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.

2. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 1 is C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl.

3. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 2 is halogen, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl.

4. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 7 is hydrogen, fluoro, cyano, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkyl.

5. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 8 is cyano or C 1 -C 4 alkyl.

6. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein X 1 is NR 3 , wherein R 3 is C 1 -C 4 alkyl.

7. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein X is S or SO 2 .

8. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 1 is C 1 -C 4 alkyl or cyclopropylmethyl and R 2 is halogen or C 1 -C 3 haloalkyl.

9. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein R 7 is hydrogen methyl, ethyl or fluoro and R 8 is methyl or ethyl.

10. The compound, or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof, according to claim 1 wherein
A is CH or N;
X is S or SO 2 ;
G 1 is N or CH;
X 1 is NCH 3 ;
R 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl;
R 2 is C 1 -C 2 haloalkyl;
R 7 is methyl; and
R 8 is methyl or ethyl.

11. 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 SO 2 ;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl;
G 1 is N or CH;
X 1 is O, S or NR 3 ; wherein R 3 is hydrogen or C 1 -C 4 alkyl;
R 2 is halogen, C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl or C 1 -C 6 haloalkoxy;
R 7 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and

R 8 is halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl.

12. A compound of formula IX,

wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl;
G 1 is N or CH;
R 3 is hydrogen or C 1 -C 4 alkyl;
R 2 is halogen, C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl or C 1 -C 6 haloalkoxy;
R 7 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and
R 8 is halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; 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 SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 7 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and
R 8 is halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; or
a compound of formula XII,

wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 7 is hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; and
R 8 is halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfanyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfinyl-C 1 -C 4 alkyl, C 1 -C 4 alkylsulfonyl-C 1 -C 4 alkyl or C 1 -C 4 alkyloxycarbonyl; or
a compound of formula XIII,

wherein
A is CH or N;
X is S, SO or SO 2 ;
R 1 is C 1 -C 4 alkyl;
R 7 is hydrogen

Assignees

• Syngenta Participations Ag

Inventors

• Rendler Sebastian
• Edmunds Andrew
• Jung Pierre Joseph Marcel
• Muehlebach Michel
• Rawal Girish
• Sen Indira
• Sikervar Vikas

Classifications

• C07D213/81

  Amides; Imides · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C07D213/78

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

• A01N43/90

  having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system · CPC title

• C07C323/62

  having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton · CPC title