Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-10894792-B2
Application number	US-201816610453-A
Country	US
Kind code	B2
Filing date	Apr 26, 2018
Priority date	May 2, 2017
Publication date	Jan 19, 2021
Grant date	Jan 19, 2021

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 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 .

Assignees

• Syngenta Participations Ag

Inventors

• Muehlebach Michel
• Edmunds Andrew
• Rendler Sebastian
• Sikervar Vikas
• Rawal Girish
• Sen Indira

Classifications

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• C07D487/06

  Peri-condensed systems · CPC title

• C07D471/06

  Peri-condensed systems · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D235/16

  Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title