Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides

Patent metadata

Field	Value
Publication number	US-9512128-B2
Application number	US-201314653515-A
Country	US
Kind code	B2
Filing date	Dec 18, 2013
Priority date	Dec 20, 2012
Publication date	Dec 6, 2016
Grant date	Dec 6, 2016

Abstract

The present invention relates to aryl sulphide and aryl sulphoxide derivatives, to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation. The aryl sulphide and aryl sulphoxide derivatives have the general structure (I)

in which the respective radicals have the meanings given in the description.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
A and B together with the carbon atoms to which they are attached represent a substructure selected

from the group consisting of

in which the labels (A) and (B) define the respective points of attachment of the radicals A and B of the general formula (I) and R 1 , R 2 and R 3 have the following meanings:
 R 1 represents hydrogen, methyl, ethyl, propyl, isobutyl, butyl, sec-butyl, isopropyl, tert-butyl, trifluoromethyl, (2,2,2)-trifluoroethyl, difluoromethyl, (2,2)-difluoroethyl, trichloromethyl, (2,2,2)-trichloroethyl, vinyl, ethynyl, allyl, butenyl, propynyl, methoxycarbonyl, ethylcarbonyl, propylcarbonyl, methoxycarbonyl, ethoxycarbonyl, methylsulphonylamino, ethylsulphonylamino, propylsulphonylamino, aminosulphonyl, methylaminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, aminothiocarbonyl, methylaminothiocarbonyl, ethylaminothiocarbonyl, dimethylaminothiocarbonyl or diethylaminothiocarbonyl;
 or represent cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which are mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, trifluoromethyl and cyclopropyl;
 or represents cyclopropylmethyl or cyclobutylmethyl which are mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl and cyclopropyl;
 R 2 and R 3 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, amino, cyano, nitro, OCN, SCN, SF 5 , trimethylsilyl, methyl, ethyl, propyl, isobutyl, butyl, sec-butyl, isopropyl, tert-butyl, trifluoromethyl, (2,2,2)-trifluoroethyl, difluoromethyl, (2,2)-difluoroethyl, trichloromethyl, (2,2,2)-trichloroethyl, vinyl, ethynyl, allyl, butenyl, propynyl, methylcarbonyl, ethylcarbonyl, propylcarbonyl, methoxycarbonyl, ethoxycarbonyl, methylsulphonylamino, ethylsulphonylamino, propylsulphonylamino, aminosulphonyl, methylaminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, dimethylaminosulphonyl, diethylaminosulphonyl, aminothiocarbonyl, methylaminothiocarbonyl, ethylaminothiocarbonyl, dimethylaminothiocarbonyl or diethylaminothiocarbonyl;
 or represent cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl which are mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, trifluoromethyl and cyclopropyl;
 or represent cyclopropylmethyl or cyclobutylmethyl which are mono- or polysubstituted by identical or different substituents from the group consisting of fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, ethoxy, trifluoromethyl and cyclopropyl;
Q represents C—V; where
V represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isobutyl, butyl, sec-butyl, isopropyl, tert-butyl, trifluoromethyl, (2,2,2)-trifluoroethyl, difluoromethyl, (2,2)-difluoroethyl;
W represents hydrogen or fluorine;
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

2. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

 in which,
Q represents C—V; where
 V represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isobutyl, butyl, sec-butyl, isopropyl, tert-butyl, trifluoromethyl, (2,2,2)-trifluoroethyl, difluoromethyl or (2,2)-difluoroethyl;
W represents hydrogen or fluorine
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

3. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

 in which,
Q represents C—V; where
 V represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isobutyl, butyl, sec-butyl, isopropyl, tert-butyl, trifluoromethyl, (2,2,2)-trifluoroethyl, difluoromethyl or (2,2)-difluoroethyl;
W represents hydrogen or fluorine;
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

4. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

 in which,
Q represents C—V; where
V represents hydrogen, methyl, ethyl or trifluoromethyl;
W represents fluorine;
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

5. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

 in which,
Q represents C—V; where
V represents hydrogen, methyl, ethyl or trifluoromethyl;
W represents fluorine;
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

6. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

in which
Q represents C—V; where
V represents hydrogen, methyl, ethyl or trifluoromethyl;
W represents fluorine;
X and Y independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano or nitro;
Z represents hydrogen;
n represents the number 0 or 1.

7. A compound according to claim 1 , wherein in formula (I)
A and B together with the carbon atoms to which they are attached represent the radical

Assignees

• Bayer Cropscience Ag

Inventors

• Alig Bernd
• Cerezo-Galvez Silvia
• Fischer Reiner
• Koehler Adeline
• Hahn Julia Johanna
• Becker Angela
• Ilg Kerstin
• Voerste Arnd
• Goergens Ulrich
• Portz Daniela

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C07D495/04

  Ortho-condensed systems · CPC title

• C07D513/04

  Ortho-condensed systems · CPC title

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• A01N43/90

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