Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-11399542-B2
Application number	US-201816628609-A
Country	US
Kind code	B2
Filing date	Jul 4, 2018
Priority date	Jul 5, 2017
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

Compounds of formula (I), wherein R2, G1, G2, X, X1, A, R4 and R5 are as defined in claim 1, and the agrochemically acceptable 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 represents CH or N;
X is S, SO or SO 2 ;
X 1 is O, S or NR 3 , wherein R 3 is C 1 -C 4 alkyl;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkylC 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;
G 1 is N or CH;
G 2 is N or CH; and
R 4 and R 5 , independently from each other, are hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl or cyano; and
agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.

2. A compound of formula 1 according to claim 1 , wherein R 4 and R 5 , independently from each other, are C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl or cyano.

3. A compound of formula I according to claim 1 , represented by the compounds of formula I-1

wherein R 2 , X 1 , A, R 4 and R 5 are as defined under formula I in claim 1 ;
Xa 1 is S, SO or SO 2 ; and
Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

4. A compound of formula I-1 according to claim 3 , wherein R 4 and R 5 , independently from each other, are C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl or cyano.

5. A compound of formula I-1 according to claim 3 , wherein X 1 is NR 3 , in which R 3 is C 1 -C 4 alkyl; and R 2 is C 1 -C 6 haloalkyl.

6. A compound of formula I-1 according to claim 3 , wherein R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl.

7. A compound of formula I according to claim 1 , represented by the compounds of formula I-2

wherein
A is CH or N;
R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; and
R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkylsulfonyl, cyano, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl.

8. A compound of formula I-2 according to claim 7 ,
wherein
A is CH or N;
R 2 is C 1 -C 6 haloalkyl; and
R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl.

9. A compound of formula I according to claim 1 , represented by the compounds of formula I-3

wherein R 2 , X 1 , A, R 4 and R 5 are as defined under formula I in claim 1 ;
Xa 2 is S, SO or SO 2 ; and
Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

10. A compound of formula I-3 according to claim 9 , wherein R 4 and R 5 , independently from each other, are C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl or cyano.

11. A compound of formula I-3 according to claim 10 , wherein R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkylsulfonyl, cyano, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl.

12. A compound of formula I according to claim 1 , represented by the compounds of formula I-4

wherein
A is CH or N;
R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; and
R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkylsulfonyl, cyano, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl.

13. A compound of formula I-4 according to claim 12 ,
wherein
A is CH or N;
R 2 is C 1 -C 6 haloalkyl; and
R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl.

14. A compound of formula I according to claim 1 , represented by the compounds of formula I-5

wherein R 2 , X 1 , A, R 4 and R 5 are as defined under formula I in claim 1 ;
Xa 3 is S, SO or SO 2 ; and
Ra 3 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

15. A compound of formula I-5 according to claim 14 , wherein R 4 and R 5 , independently from each other, are C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 6 cycloalkylC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 haloalkenyl, C 3 -C 6 halocycloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 6 haloalkoxy, C 1 -C 4 alkylsulfonyl, C 3 -C 6 cycloalkylsulfonyl, C 1 -C 4 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 4 alkoxycarbonyl or cyano.

16. A compound of formula I-5 according to claim 15 , wherein R 4 and R 5 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkylsulfonyl, cyano, C 1 -C 4 alkylsulfonylC 1 -C 4 alkyl, C 1 -C 4 alkylsulfanylC 1 -C 4 alkyl, C 1 -C 6 alkoxyC 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkylcarbonyl or C 1 -C 4 alkoxycarbonyl.

17. A compound of formula I according to claim 1 , represented by the compounds of formula I-6

wherein
A is CH or N;
R

Assignees

• Syngenta Participations Ag

Inventors

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

Classifications

• A01N43/76

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title

• C07D235/26

  Oxygen atoms · CPC title

• A01N43/52

  condensed with carbocyclic rings, e.g. benzimidazoles · CPC title

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C07D413/10

  linked by a carbon chain containing aromatic rings · CPC title