IP Library Granted Patent US 10,894,792
Granted Patent B2
US 10,894,792 · App. 16/610,453 · Granted Jan 19, 2021

Pesticidally active heterocyclic derivatives with sulfur containing substituents

Inventors: Michel Muehlebach (Stein, CH); Andrew Edmunds (Stein, CH); Sebastian Rendler (Stein, CH); Vikas Sikervar (Goa, IN); Girish Rawal (Goa, IN); Indira Sen (Goa, IN)
Assignee: SYNGENTA PARTICIPATIONS AG
C07D471/04A01N43/90C07D487/04
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Quick Facts
Patent No.
US 10,894,792
App. No.
16/610,453
Granted
Jan 19, 2021
Kind
B2
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.

Claims (89)

1. A compound of formula I

wherein

A is CH or N;

X is S, SO or SO2;

R1 is C1-C4alkyl, C1-C4haloalkyl or C3-C6cycloalkyl-C1-C4alkyl;

R7 and R8 are, independently from each other, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl,

C1-C6cyanoalkyl, C1-C4alkoxyC1-C4alkyl, pyridyl or phenyl, wherein said pyridyl or phenyl can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy, C1-C4alkoxy, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl and C(O)C1-C4haloalkyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4alkoxy and C1-C4haloalkyl; and said ring system may contain one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur;

n is 0 or 1;

Q is a radical selected from the group consisting of formula Q1 to Q4

wherein

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

and wherein

X1 is 0, S or NR3, wherein R3 is C1-C4alkyl;

R2 is halogen, C1-C6haloalkyl, C1-C4haloalkylsulfanyl, C1-C4haloalkylsulfinyl, C1-C4haloalkylsulfonyl or C1-C6haloalkoxy;

G1 is N or CH;

G2 and G3 are, independently from each other, N or CH; and

agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of the compounds of formula I.

2. The compound of formula I according to claim 1 , wherein

R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. The compound of formula I according to claim 1 , wherein

Q is Q1; and

R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

4. The compound of formula I according to claim 1 ,

wherein

X is SO2;

R1 is ethyl;

Q is Q1;

X1 is NR3, and R3 is methyl;

A is N;

R2 is C1-C6haloalkyl;

G1 is N or CH;

n is 0 or 1;

R7 and R8 are, independently from each other, C1-C6alkyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a six-membered, saturated ring system which can contain one oxygen atom.

5. The compound of formula I according to claim 1 , wherein

Q is Q2; and

R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

6. The compound of formula I according to claim 1 ,

wherein

Q is Q2;

X is SO2;

R1 is ethyl;

R2 is C1-C6haloalkyl;

n is 0 or 1; and

R7 and R8 are, independently from each other, C1-C6alkyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a six-membered, saturated ring system, which can contain one oxygen atom.

7. The compound of formula I according to claim 1 ,

Q is Q4; and

R1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

8. The compound of formula I according to claim 1 ,

wherein

Q is Q4;

X is SO2:

R1 is ethyl;

X1 is NR3, and R3 is methyl;

A is N;

R2 is C1-C6haloalkyl;

n is 0 or 1; and

R7 and R8 are, independently from each other, C1-C6alkyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a six-membered, saturated ring system, which can contain one oxygen atom.

9. The compound of formula I according to claim 1 ,

wherein

X is SO2;

R1 is ethyl;

R7 and R8 are, independently from each other, C1-C6alkyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a six-membered, saturated ring system, which can contain one oxygen atom;

Q is a radical selected from the group consisting of formula Q1a, Q1b and Q2a

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

and

R2 is C1-C6haloalkyl.

10. The compound of formula I according to claim 1 , wherein

X is SO2;

R1 is ethyl;

R2 is trifluoromethyl; and

X1 is NR3, and R3 is methyl.

11. The compound of formula I according to claim 10 , wherein

R7 and R8 are, independently from each other, C1-C6alkyl, C1-C6haloalkyl, C3-C6cycloalkyl, C1-C6cyanoalkyl, or C1-C4alkoxyC1-C4alkyl.

12. The compound of formula I according to claim 10 , wherein

R7 and R8, together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, said ring system can be mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C1-C4alkyl, C1-C4alkoxy and C1-C4haloalkyl; and said ring system may contain one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur.

13. The compound of formula I according to claim 10 , wherein

R7 and R8, together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, and said ring system may contain one heteroatom selected from the group consisting of nitrogen, oxygen and sulfur.

14. The compound of formula I according to claim 10 , wherein

R7 and R8 are, independently from each other, methyl or ethyl; or

R7 and R8, together with the sulfur atom to which they are attached, form a six-membered, saturated ring system, which can contain one oxygen atom, or form a four-membered saturated ring system.

15. A compound selected from:

16. A pesticidal composition, comprising: at least one compound of formula I according to claim 1 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.

17. A method for controlling pests, comprising: applying a composition according to claim 16 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

18. A method for the protection of plant propagation material from the attack by pests, comprising: treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 16 .

Assignments (3)
CHANGE OF NAME Recorded Apr 28, 2025
From: SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 071085/0107 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE MAILING ADDRESS PREVIOUSLY RECORDED ON REEL 050930 FRAME 0702. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Nov 13, 2019
From: MUEHLEBACH, MICHEL; EDMUNDS, ANDREW; RENDLER, SEBASTIAN; SIKERVAR, VIKAS; RAWAL, GIRISH; SEN, INDIRA
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 051003/0200 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2019
From: MUEHLEBACH, MICHEL; EDMUNDS, ANDREW; RENDLER, SEBASTIAN; SIKERVAR, VIKAS; RAWAL, GIRISH; SEN, INDIRA
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 050930/0702 →