IP Library › Granted Patent US 11,399,542

Granted Patent B2

US 11,399,542 · App. 16/628,609 · Granted Aug 2, 2022

Pesticidally active heterocyclic derivatives with sulfur containing substituents

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

Assignee: SYNGENTA PARTICIPATIONS AG

A01N43/90 A01N43/52 A01N43/76 C07D403/10 C07D413/10 C07D471/04 C07D487/04 C07D519/00

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Quick Facts

Patent No.: US 11,399,542
App. No.: 16/628,609
Granted: Aug 2, 2022
Kind: B2

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Abstract

Compounds of formula (I), wherein R 2 , G 1 , G 2 , X, X 1 , A, R 4 and R 5 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.

Claims (252)

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

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 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl or C 1 -C 4 haloalkylsulfonyl; and

18. A compound of formula I-6 according to claim 17 ,

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.

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

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

Xa 4 is S, SO or SO 2 ;

Ra 4 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl; and

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.

20. A compound of formula I-7 according to claim 19 , 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.

21. A compound of formula I according to claim 1 , represented by the compounds of formula I-8

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

22. A compound of formula I-8 according to claim 21 ,

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.

23. A compound of formula I according to claim 1 , represented by the compounds of formula I-8a

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;

R 5 is C 1 -C 6 alkyl; and

R 4 is 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.

24. A compound of formula I-8a according to claim 23 ,

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.

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

wherein

A is CH or N;

R 4 and R 5 are, independently from each other, hydrogen or C 1 -C 6 alkyl; and

Q is a radical selected from the group consisting of formula Q 1 , Q 2 , Q 3 and Q 4

in wherein the arrow denotes the point of attachment to the bicyclic ring incorporating the radical A;

and in which

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

X 1 is O or NR 3 , in which R 3 is C 1 -C 4 alkyl.

26. A compound of formula 1-9 according to claim 25 ,

wherein

Q is selected from the group consisting of formula Q 1 , Q 2 and Q 3 ;

wherein the arrow denotes the point of attachment to the bicyclic ring incorporating the radical A;

and in which

R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl or C 1 -C 4 haloalkylsulfonyl; and

X 1 is O or NR 3 , in which R 3 is C 1 -C 4 alkyl.

27. A compound of formula I-9 according to claim 25 , wherein X 1 is NR 3 , in which R 3 is C 1 -C 4 alkyl.

28. A compound of formula I according to claim 1 , represented by the compounds of formula I-10

wherein

A is CH or N;

Q is a radical selected from the group consisting of formula Q 1 , Q 2 , Q 3 and Q 4

wherein the arrow denotes the point of attachment to the bicyclic ring incorporating the radical A;

and in which

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

X 1 is O or NR 3 , in which R 3 is C 1 -C 4 alkyl.

29. A compound of formula I according to claim 1 , represented by the compounds of formula I-11

wherein

A is CH or N;

R 4 and R 5 are methyl; and

Q is a radical selected from the group consisting of formula Q 1 , Q 2 , Q 3 and Q 4

wherein the arrow denotes the point of attachment to the bicyclic ring incorporating the radical A;

and in which

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

X 1 is O or NCH 3 .

30. A pesticidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of claim 1 and, optionally, at least one auxiliary or diluent.

31. A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of the pest, or to a plant susceptible to attack by the pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of claim 1 .

32. A method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with the composition according to claim 30 .

33. A compound of formula XIVx,

wherein

A is CH or N;

X is S, SO or SO 2 ;

R 1 is C 1 -C 4 alkyl;

R 00 is C 1 -C 4 alkyl; and

R 4x and R 5x , independently from each other, are hydrogen or C 1 -C 6 alkyl.

34. A compound of formula XIIIx,

wherein

A is CH or N;

X is S, SO or SO 2 ;

R 1 is C 1 -C 4 alkyl; and

R 4x and R 5x , independently from each other, are hydrogen or C 1 -C 6 alkyl.

35. A compound of formula XIIx,

wherein

A is CH or N;

X is S, SO or SO 2 ;

R 1 is C 1 -C 4 alkyl; and

R 4x and R 5x , independently from each other, are hydrogen or C 1 -C 6 alkyl.

36. A compound of formula II-ab,

wherein

A is CH or N;

X is S, SO or SO 2 ;

R 1 is C 1 -C 4 alkyl;

X 1x is O or NCH 3 ;

R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl or C 1 -C 4 haloalkylsulfonyl;

G 1 is N or CH;

G 2 is N or CH; and

R 5y is C 1 -C 6 alkyl.

37. A compound of formula XIx,

or a regioisomer thereof, or an isomeric mixture (in any ratio) thereof;

wherein

A is CH or N;

X is S, SO or SO 2 ;

R 1 is C 1 -C 4 alkyl;

X 1x is O or NCH 3 ;

R 2 is C 1 -C 6 haloalkyl, C 1 -C 4 haloalkylsulfanyl or C 1 -C 4 haloalkylsulfonyl;

G 1 is N or CH;

G 2 is N or CH; and

R 4x and R 5x , independently from each other, are hydrogen or C 1 -C 6 alkyl.

38. The compound of claim 33 , wherein

X is S or SO 2 ;

R 1 is ethyl;

R 00 is methyl, ethyl or tert-butyl; and

R 4x and R 5x , independently from each other, are hydrogen, methyl or ethyl.

39. The compound of claim 34 , wherein

X is S or SO 2 ;

R 1 is ethyl; and

R 4x and R 5x , independently from each other, are hydrogen, methyl or ethyl.

40. The compound of claim 35 , wherein

X is S or SO 2 ;

R 1 is ethyl; and

R 4x and R 5x , independently from each other, are hydrogen, methyl or ethyl.

41. The compound of claim 36 , wherein

A is CH;

X is S or SO 2 ;

R 1 is ethyl;

R 2 is trifluoromethyl, trifluoromethylsulfanyl or trifluoromethylsulfonyl; and

R 5y is methyl or ethyl.

42. The compound of claim 37 , wherein

A is CH;

X is S or SO 2 ;

R 1 is ethyl;

R 2 is trifluoromethyl, trifluoromethylsulfanyl or trifluoromethylsulfonyl;

R 4x and R 5x , independently from each other, are hydrogen, methyl or ethyl.

43. A compound selected from a compound of formula I-1, a compound of formula I-3, a compound of formula I-5, and a compound of formula I-7

wherein

A represents CH or N;

X a1 , X a2 , X a3 , and X a4 are selected from S and SO 2 ;

X 1 is O or NR 3 , wherein R 3 is C 1 -C 4 alkyl;

R a1 , R a2 , R a3 , and R a4 are selected from methyl, ethyl, n-propyl, i-propyl, and cyclopropylmethyl;

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 4 and R 5 , independently from each other, are methyl, ethyl, cyclopropylsulfonyl, cyano, methylsulfonylmethyl, methylsulfanylmethyl, methoxymethyl, 2,2,2-trifluoroethyl, cyclopropylcarbonyl or ethoxycarbonyl; and

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

44. The compound of claim 43 , wherein R 4 and R 5 are, independently from each other, methyl or ethyl.

45. The compound of claim 43 , 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.

46. The compound of claim 45 , wherein R 4 and R 5 are, independently from each other, methyl or ethyl.

47. A pesticidal composition comprising an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of claim 43 , and optionally at least one auxiliary or diluent.

48. A method of combating and controlling insects, acarines, nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest an insecticidally, acaricidally, nematicidally or molluscicidally effective amount of the compound of claim 43 .

49. A method for the protection of plant propagation material from the attack by insects, acarines, nematodes or molluscs, which comprises treating the propagation material or the site, where the propagation material is planted, with the composition according to claim 47 .

50. A compound selected from:

1-ethyl-6-ethylsulfanyl-3-methyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]benzimidazol-2-one;

1-ethyl-6-ethylsulfanyl-3-methyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

1-ethyl-6-ethylsulfonyl-3-methyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridin-2-yl]benzimidazol-2-one;

1-ethyl-6-ethylsulfonyl-3-methyl-5-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

1-ethyl-5-ethylsulfonyl-3-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

1-ethyl-5-ethylsulfanyl-3-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-c]pyridin-2-yl]imidazo[4,5-b]pyridin-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-c]pyridin-2-yl]benzimidazol-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-c]pyridin-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[7-methyl-3-(trifluoromethyl) imidazo[4,5-c]pyridazin-6-yl]benzimidazol-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

1-cyclopropylsulfonyl-5-ethylsulfonyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]-2-oxo-benzimidazole-1-carbonitrile;

5-ethylsulfanyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]-2-oxo-benzimidazole-1-carbonitrile;

6-ethylsulfonyl-1-methyl-3-(methylsulfonylmethyl)-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1-methyl-3-(methylsulfanylmethyl)-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-1-(methoxy-methyl)-3-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1-methyl-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]-3-(2,2,2-trifluoroethyl) benzimidazol-2-one;

1-(cyclopropanecarbonyl)-5-ethylsulfonyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[7-methyl-3-(trifluoromethyl) imidazo[4,5-c]pyridazin-6-yl]imidazo[4,5-b]pyridine-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]imidazo[4,5-b]pyridine-2-one;

ethyl 5-ethylsulfonyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]-2-oxo-benzimidazole-1-carboxylate;

6-ethylsulfanyl-1,3-dimethyl-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]imidazo[4,5-b]pyridine-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[5-(trifluoromethylsulfonyl)-1,3-benzoxazol-2-yl]imidazo[4,5-b]pyridine-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[7-methyl-3-(trifluoromethyl) imidazo[4,5-c]pyridazin-6-yl]benzimidazol-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]benzimidazol-2-one;

1-cyclopropylsulfonyl-5-ethylsulfanyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

5-ethylsulfanyl-1-(methoxy-methyl)-3-methyl-6-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

6-ethylsulfanyl-1-methyl-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]-3-(2,2,2-trifluoroethyl) benzimidazol-2-one;

1-(cyclopropanecarbonyl)-5-ethylsulfanyl-3-methyl-6-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridine-2-yl]benzimidazol-2-one;

6-ethylsulfanyl-1-methyl-3-(methylsulfanylmethyl)-5-[3-methyl-6-(trifluoromethyl) imidazo[4,5-b]pyridin-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[5-(trifluoromethylsulfanyl)-1,3-benzoxazol-2-yl]imidazo[4,5-b]pyridin-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[1-methyl-5-(trifluoromethyl-sulfanyl)benzimidazol-2-yl]benzimidazol-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[1-methyl-5-(trifluoromethyl-sulfonyl)benzimidazol-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[1-methyl-5-(trifluoromethyl-sulfanyl)benzimidazol-2-yl]imidazo[4,5-b]pyridin-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[1-methyl-5-(trifluoromethyl-sulfonyl)benzimidazol-2-yl]imidazo[4,5-b]pyridine-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]benzimidazol-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[5-(trifluoromethyl)-1,3-benzoxazol-2-yl]benzimidazol-2-one;

5-ethylsulfanyl-1,3-dimethyl-6-[1-methyl-5-(trifluoromethyl-sulfanyl)benzimidazol-2-yl]benzimidazol-2-one;

6-ethylsulfonyl-1,3-dimethyl-5-[1-methyl-5-(trifluoromethyl-sulfinyl)benzimidazol-2-yl]imidazo[4,5-b]pyridin-2-one;

5-ethylsulfonyl-1,3-dimethyl-6-[1-methyl-5-(trifluoromethyl-sulfinyl)benzimidazol-2-yl]benzimidazol-2-one; and

6-ethylsulfonyl-1,3-dimethyl-5-[5-(trifluoromethylsulfinyl)-1,3-benzoxazol-2-yl]imidazo[4,5-b]pyridin-2-one.

Assignments (2)

MERGER AND CHANGE OF NAME Recorded Feb 28, 2025

From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG

To: SYNGENTA CROP PROTECTION AG

Reel/Frame 070362/0665 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 7, 2020

From: RAWAL, GIRISH; JUNG, PIERRE JOSEPH MARCEL; EDMUNDS, ANDREW; SIKERVAR, VIKAS; SEN, INDIRA; RENDLER, SEBASTIAN; MUEHLEBACH, MICHEL; BUCHHOLZ, ANKE; EMERY, DANIEL

To: SYNGENTA PARTICIPATIONS AG

Reel/Frame 051438/0590 →