Pesticidally active heterocyclic derivatives with sulfur containing substituents

Patent metadata

Field	Value
Publication number	US-10961248-B2
Application number	US-201716465014-A
Country	US
Kind code	B2
Filing date	Nov 24, 2017
Priority date	Dec 1, 2016
Publication date	Mar 30, 2021
Grant date	Mar 30, 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 SO 2 ;
R 1 is C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl;
R 7 and R 8 are, independently from each other, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 cyanoalkyl, C 1 -C 4 alkoxyC 1 -C 4 alkyl, pyridyl or phenyl, wherein said pyridyl or 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
R 7 and R 8 , 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, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 haloalkyl; 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 Q 1 to Q 3

wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and wherein
X 1 is O, S or NR 3 , wherein R 3 is C 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 and G 3 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 claim 1 ,
wherein
R 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. The compound of claim 1 ,
wherein
Q is Q 1 ; and
R 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

4. The compound of claim 1 ,
wherein
Q is Q 1 ;
X 1 is NR 3 , and R 3 is methyl;
X is SO 2 ;
R 1 is ethyl;
A is CH or N;
R 2 is C 1 -C 6 haloalkyl;
G 1 is N or CH;
n is 0 or 1; and
R 7 and R 8 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl monosubstituted by C 1 -C 4 alkyl, or
R 7 and R 8 , together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system which can contain one oxygen atom.

5. The compound of claim 1 ,
wherein
Q is Q 2 ; and
R 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

6. The compound of claim 1 ,
wherein
Q is Q 2 ;
X is SO 2 ;
R 1 is ethyl;
A is CH or N;
R 2 is C 1 -C 6 haloalkyl;
G 3 is N or CH;
n is 0 or 1; and
R 7 and R 8 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl monosubstituted by C 1 -C 4 alkyl; or
R 7 and R 8 , together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, and said ring system can contain one oxygen atom.

7. The compound of claim 1 ,
wherein
X is SO 2 ;
R 1 is ethyl;
A is CH or N;
n is 0 or 1;
R 7 and R 8 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl monosubstituted by C 1 -C 4 alkyl; or
R 7 and R 8 , together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, and said ring system can contain one oxygen atom; and
Q is a radical selected from the group consisting of formula Q 1a , Q 1b , Q 2a and Q 3a

wherein the arrow denotes the point of attachment to the ring incorporating the radical A;
and
R 2 is C 1 -C 6 haloalkyl.

8. The compound of claim 1 ,
wherein
Q is Q 3 ; and
R 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

9. The compound of claim 1 ,
wherein
Q is Q 2 ;
X is SO 2 ;
R 1 is ethyl;
A is CH or N;
R 2 is C 1 -C 6 haloalkyl;
G 2 is CH;
G 3 is N or CH;
n is 0 or 1; and
R 7 and R 8 are, independently from each other, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl or phenyl which phenyl is monosubstituted by C 1 -C 4 alkyl; or
R 7 and R 8 , together with the sulfur atom to which they are attached, form a four- to six-membered, saturated ring system, and said ring system can contain one oxygen atom.

10. A pesticidal composition, which comprises a compound of formula I according to claim 1 or, where appropriate, a tautomer thereof, in free form or in agrochemically utilizable salt form, as active ingredient and at least one auxiliary.

11. A method for controlling pests, which comprises applying a composition according to claim 10 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.

12. 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 10 .

13. A process for the preparation of a compound of formula (XI-A)

or a salt thereof; wherein Rf is C 1 -C 6 haloalkyl; comprising
a. reacting a compound of formula 14

wherein Y 1 is independently halogen or C 1 -C 4 -alkoxy; or
the two radicals Y 1 in a compound of formula 14 together form a group —O—(CH 2 ) m —O—, wherein m is 2, 3 or 4; with a compound of formula 15

wherein Rf is C 1 -C 6 haloalkyl; and
Y 2 is C 1 -C 6 alkoxy, chloro, fluoro or C 1 -C 6 dialkylamino;
in the presence of a base to produce a compound of formula 16

or a salt thereof; or tautomers and E/Z isomers thereof; wherein Rf is C 1 -C 6 haloalkyl; and
Y 1 is independently halogen or C 1 -C 4 -alkoxy; or
the two radicals Y 1 in a compound of formula 16 together form a group —O—(CH 2 ) m —O—, wherein m is 2, 3 or 4; and
b. reacting a compound of formula 16

or a salt thereof;
or tautomers and E/Z isomers thereof; wherein Rf is C 1 -C 6 haloalkyl; and
Y 1 is independently halogen or C 1 -C 4 -alkoxy; or
the two radicals Y 1 in a compound of formula 16 together form a group —O—(CH 2 ) m —O—, wherein m is 2, 3 or 4;
with ammonia, or a salt thereof; to produce a compound of formula 17

or tautomers and E/Z isomers thereof; wherein Rf is C 1 -C 6 haloalkyl; and
Y 1 is independently halogen or C 1 -C 4 -alkoxy; or
the two radicals Y 1 in a compound of formula 17 together form a group —O—(CH

Assignees

• Syngenta Participations Ag

Inventors

• Edmunds Andrew
• Muehlebach Michel
• Jung Pierre Joseph Marcel
• Rendler Sebastian
• Sikervar Vikas
• Rawal Girish
• Sen Indira
• Mondiere Régis Jean Georges
• Smejkal Tomas
• El Qacemi Myriem
• Gribkov Denis

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07C225/14

  the carbon skeleton being unsaturated · CPC title

• C07D213/74

  Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals · CPC title

• A01P5/00

  Nematocides · CPC title