Pesticidally active amide heterocyclic derivatives with sulphur containing substituents

Patent metadata

Field	Value
Publication number	US-10071997-B2
Application number	US-201515531557-A
Country	US
Kind code	B2
Filing date	Nov 24, 2015
Priority date	Dec 1, 2014
Publication date	Sep 11, 2018
Grant date	Sep 11, 2018

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;
Q is attached to the 3- or 4-position; and is phenyl which 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
Q is a five- to ten-membered monocyclic or fused bicyclic ring system linked via a carbon atom to the ring which contains the group A, said ring system can be aromatic, partially saturated or fully saturated and contains 1 to 4 hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, it not being possible for each ring system to contain more than 2 oxygen atoms and more than 2 sulfur atoms, said five- to ten-membered ring system can be mono- to polysubstituted by substituents independently 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 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or
Q is a five- to six-membered, aromatic, partially saturated or fully saturated ring system linked via a nitrogen atom to the ring which contains the group A, 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 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; and said ring system contains 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, where said ring system may not contain more than one oxygen atom and not more than one sulfur atom; or
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, wherein 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
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 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl and phenyl, wherein 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 halo-alkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; 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, wherein 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 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl; or
Q is C 1 -C 6 haloalkylsulfanyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 haloalkoxy, —C(O)C 1 -C 4 haloalkyl, C 1 -C 6 alkylsulfanyl, C 1 -C 6 alkylsulfinyl, or C 1 -C 6 alkylsulfonyl;
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
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 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;
X 1 is S; or
X 1 is N—R 4 , wherein R 4 is hydrogen or C 1 -C 4 alkyl;
X 2 is N or C—R 5 , wherein R 5 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or cyano;
R 2 is hydrogen, 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 haloalkylsulfanyl, —O(C 1 -C 4 haloalkyl), or —C(O)C 1 -C 4 haloalkyl;
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;
Y is O or S;
and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

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

wherein:
Y, R 2 , R 3 , X 2 and Q are as defined under formula I in claim 1 ;
Xa 1 is S, SO or SO 2 ; and
Ra 1 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

3. A compound of Formula I-1 according to claim 2 , wherein Q is selected from the group consisting of J-1 to J-45 wherein the arrow represents the point of attachment of the heterocycle to the radical Q:

wherein each group J-1 to J-45 is mono- di- or trisubstituted with R x ,
wherein each R x is, independently selected from the group consisting of hydrogen, 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 alkylsulfanyl, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, —C(O)C 1 -C 4 alkyl, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl and —C(O)C 1 -C 4 haloalkyl.

4. A compound of Formula 1 according to claim 1 , represented by the Formula 1-2:

wherein:
Y, R 2 , R 3 , X 2 and Q are as defined under formula 1 in claim 1 ;
Xa 2 is S, SO or SO 2 ; and
Ra 2 is methyl, ethyl, n-propyl, i-propyl or cyclopropylmethyl.

5. A compound of Formula I-2 according to claim 4 , wherein Q is selected from the group consisting of J-1 to J-45 wherein the arrow represents the point of attachment of the heterocycle to the radical Q:

wherein each group J-1 to J-45 is mono- di- or trisubstituted with Rx,
wherein each R x is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 4

Assignees

• Syngenta Participations Ag

Inventors

• Muehlebach Michel
• Edmunds Andrew
• Jeanguenat Andre
• Jung Pierre Joseph Marcel
• Renold Peter
• Hueter Ottmar Franz

Classifications

• C07D417/12 Primary

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title

• C07D417/14 Primary

  containing three or more hetero rings · CPC title