Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-12421237-B2
Application number	US-202117468051-A
Country	US
Kind code	B2
Filing date	Sep 7, 2021
Priority date	Dec 15, 2016
Publication date	Sep 23, 2025
Grant date	Sep 23, 2025

Abstract

Compounds of formula I

wherein the substituents 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

The invention 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, 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.

Assignees

• Syngenta Participations Ag
• Syngenta Crop Protection Ag

Inventors

• Edmunds Andrew
• Rendler Sebastian
• Muehlebach Michel
• Emery Daniel
• Buchholz Anke
• Sikervar Vikas
• Rawal Girish

Classifications

• A01N43/90

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

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title