Pesticidally active heterocyclic derivatives with sulphur containing substituents

Patent metadata

Field	Value
Publication number	US-9809587-B2
Application number	US-201515505758-A
Country	US
Kind code	B2
Filing date	Aug 18, 2015
Priority date	Aug 25, 2014
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

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 CH or N;
Q is a five- to ten-membered monocyclic or fused bicyclic heterocyclic ring system which can be aromatic, partially saturated or fully saturated and which 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, oxo, OH, NH 2 , C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 halo-alkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 halo-alkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino;
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; and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds.

2. A compound of formula I according to claim 1 , wherein
Q is selected from the group consisting of

wherein each group J-1 to J-56 is mono- di- or trisubstituted with Rx, wherein each Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, and C 1 -C 6 di-alkylamino.

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

wherein
R 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.

4. A compound of formula I-1 according to claim 3 , wherein
Q is selected from the group consisting of the heterocycles

wherein Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylamino, C 1 -C 6 di-alkylamino, C 1 -C 6 alkoxycarbonylamino, C 1 -C 4 haloalkylsulfanyl, C 1 -C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl; wherein said phenyl, pyrimidinyl, thiazolyl, pyridinyl, pyrazinyl, pyridazinyl, pyrazinyloxy, imidazolyl, dihydro-oxazolyl, oxazolyl, dioxolanyl, 1,3-dioxanyl and 5,6-dihydro-[1,4,2]dioxazinyl itself can be mono- to polysubstituted by substituents independently selected from the group consisting of halogen, C 1 -C 6 alkyl, di-C 1 -C 4 alkyl-phosphinoylmethyl-aminocarbonyl, C 1 -C 6 alkoxycarbonylamino, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylamino and C 1 -C 6 di-alkylamino.

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

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

6. A compound of formula I-2 according to claim 5 , wherein
Q is selected from the group consisting of the heterocycles

wherein Rx is, independently selected from the group consisting of hydrogen, halogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio

Assignees

• Syngenta Participations Ag

Inventors

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

Classifications

• C07D471/04 Primary

  Ortho-condensed systems · CPC title

• A01N43/90

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

• C07D487/02

  in which the condensed system contains two hetero rings · CPC title

• C07D417/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• C07F5/02

  Boron compounds · CPC title