Granted Patent B2

US 12,421,237 · App. 17/468,051 · Granted Sep 23, 2025

Inventors: Andrew Edmunds (Stein, CH); Sebastian Rendler (Stein, CH); Michel Muehlebach (Stein, CH); Daniel Emery (Stein, CH); Anke Buchholz (Stein, CH); Vikas Sikervar (Goa, IN); Girish Rawal (Goa, IN)

Assignee: SYNGENTA CROP PROTECTION AG

C07D487/04A01N43/90

Abstract

Claims (61)

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, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl; or

R 1 is C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl; or

R 1 is C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl or C 2 -C 6 alkynyl;

R 2 is halogen, cyano, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkyl substituted by one or two substituents selected from the group consisting of hydroxyl, methoxy and cyano; or

R 2 is C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, O(C 1 -C 4 haloalkyl), —C(O)C 1 -C 4 haloalkyl; or

R 2 is C 3 -C 6 cycloalkyl which can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano and C 1 -C 4 alkyl;

X 1 is O, S or NR 3 , wherein R 3 is hydrogen, C 1 -C 4 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl or C 3 -C 6 cycloalkyl;

Z 1 is cyano, formyl, hydroxyl, C 3 -C 6 cycloalkyl, hydroxycarbonyl, aminocarbonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 haloalkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, di-(C 1 -C 4 ) alkylaminocarbonyl, C 1 -C 4 alkylaminocarbonyl, amino, C 1 -C 4 alkylcarbonylamino, di-(C 1 -C 4 ) alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino or a group —C(R 5 )—NOR 6 , wherein R 5 and R 6 are independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl; or

Z 1 is phenyl, said phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or

Z 1 is C 1 -C 4 alkyl which is mono- or polysubstituted by the group Z 2 ;

Z 2 is cyano, formyl, hydroxyl, C 3 -C 6 cycloalkyl, hydroxycarbonyl, aminocarbonyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 haloalkoxycarbonyl, C 1 -C 4 alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, di-(C 1 -C 4 ) alkylaminocarbonyl, C 1 -C 4 alkylaminocarbonyl, amino, C 1 -C 4 alkylcarbonylamino, di-(C 1 -C 4 ) alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, a group —C(R 5 )—NOR 6 , wherein R 5 and R 6 are independently hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;

R 1a is hydrogen, C 1 -C 2 alkyl, C 1 -C 4 alkoxy or halogen; and

n is 1 or 2; or

agrochemically acceptable salts, stereoisomers, enantiomers, tautomers, or N-oxides thereof.

2. The compound of claim 1 , represented by the compounds of formula I-1

wherein X 1 , A, R 2 , R 1a and Z 1 are as defined under formula I in claim 1 ;

X a1 is S, SO or SO 2 ; and

R a1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. The compound of claim 1 , represented by the compounds of formula I-2

wherein A, R 2 and Z 1 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.

4. The compound of claim 1 , represented by the compounds of formula I-3

wherein

A is CH or N;

X a3 is S or SO 2 ;

R a3 is ethyl;

R 2 is C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 2 haloalkylsulfinyl, C 1 -C 2 haloalkylsulfonyl; and

Z 1 is cyano, hydroxycarbonyl, aminocarbonyl, C 1 -C 4 alkoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, amino, methoxycarbonylamino, formyl, hydroxymethylene or methylhydroxymethylene.

5. A pesticidal composition, comprising:

at least one compound of formula I according to claim 1 as an active ingredient; and

at least one auxiliary.

6. A method for controlling pests, which comprises applying a composition according to claim 5 to the pests or their environment.

7. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 5 .

8. A pesticidal composition, comprising:

at least one compound of formula I according to claim 2 as an active ingredient; and

at least one auxiliary.

9. A method for controlling pests, which comprises applying a composition according to claim 8 to the pests or their environment.

10. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 8 .

11. A pesticidal composition, comprising:

at least one compound of formula I according to claim 3 as active ingredient; and

at least one auxiliary.

12. A method for controlling pests, which comprises applying a composition according to claim 11 to the pests or their environment.

13. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 11 .

14. A pesticidal composition, which comprises at least one compound of formula I according to claim 4 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.

15. A compound selected from:

16. The compound of claim 15 , wherein the compound is

17. The compound of claim 15 , wherein the compound is

18. A compound of formula I-3

wherein

A is CH or N;

X a3 is S or SO 2 ;

R a3 is ethyl;

R 2 is C 1 -C 4 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 2 haloalkylsulfinyl, C 1 -C 2 haloalkylsulfonyl; and

Z 1 is cyano.

19. The compound of claim 18 , wherein R 2 is C 1 -C 4 haloalkyl.

Assignments (1)

Priority Claims (1)

Continuity (2)

References Cited (16)