Pesticidally active heterocyclic derivatives with sulphur containing substituents

Patent metadata

Field	Value
Publication number	US-10081641-B2
Application number	US-201515504688-A
Country	US
Kind code	B2
Filing date	Aug 18, 2015
Priority date	Aug 21, 2014
Publication date	Sep 25, 2018
Grant date	Sep 25, 2018

Abstract

Compounds of formula (I), wherein the substituents are as defined in claim 1 , and the agrochemically acceptable salts 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 represents N;
Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl; or
Q is C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl; or
Q is C 2 -C 6 alkynyl, or C 2 -C 6 alkynyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, tri(C 1 -C 4 alkyl)silyl and phenyl;
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, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl or 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), or 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;

or an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

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

wherein
R 2 and Q are as defined under formula I in claim 1 ;
Xa 10 is S, SO or SO 2 ; and
Ra 10 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. A compound of formula I-10 according to claim 2 , wherein Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or disubstituted by substituents selected from the group consisting of cyano, C 1 -C 4 haloalkyl and halogen; or Q is C 2 -C 6 alkenyl, or C 2 -C 6 alkenyl monosubstituted by substituents selected from the group consisting of C 1 -C 4 alkyl and C 3 -C 6 cycloalkyl; or Q is C 2 -C 6 alkynyl, or C 2 -C 6 alkynyl monosubstituted by substituents selected from the group consisting of tri(C 1 -C 4 alkyl)silyl, phenyl and phenyl which itself can be monosubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl.

4. A compound of formula I according to claim 1 represented by the compounds of formula Ia

wherein
X 2 is SO 2 ;
X 3 is N—(C 1 -C 4 alkyl);
R 4 is C 1 -C 4 alkyl;
Q a is C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, or is C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl each mono- or disubstituted by substituents selected from the group consisting of halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano, C 3 -C 6 cycloalkyl, tri(C 1 -C 4 alkyl)silyl and phenyl, said phenyl can be mono-substituted by halogen or C 1 -C 4 haloalkyl; or Q a is C 3 -C 6 cycloalkenyl which itself can be mono- or di-substituted by C 1 -C 4 alkyl; and
R 6 is C 1 -C 4 haloalkyl.

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

6. A compound of formula I according to claim 1 , wherein Q is C 3 -C 6 cycloalkyl, or C 3 -C 6 cycloalkyl mono- or polysubstituted by substituents selected from the group consisting of halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl and phenyl.

7. A compound of formula I according to claim 6 , wherein Q is C 3 -C 6 cycloalkyl monosubstituted by cyano.

Assignees

• Syngenta Participations Ag

Inventors

• Stoller Andre
• Jeanguenat Andre
• Edmunds Andrew
• Jung Pierre Joseph Marcel
• Emery Daniel
• Muehlebach Michel
• Renold Peter

Classifications

• C07F7/0812 Primary

  comprising a heterocyclic ring · CPC title

• C07F5/025

  Boronic and borinic acid compounds · CPC title

• C07D471/04

  Ortho-condensed systems · CPC title

• C07D213/79 Primary

  Acids; Esters · CPC title

• A01N43/90

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