Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides

Patent metadata

Field	Value
Publication number	US-2016145235-A1
Application number	US-201414899259-A
Country	US
Kind code	A1
Filing date	Jun 16, 2014
Priority date	Jun 20, 2013
Publication date	May 26, 2016
Grant date	—

Abstract

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

in which the respective radicals are as defined in the description.

First claim

1 . Compound of formula (I)

in which
A and B together with the atoms to which they are bonded are an optionally substituted five-membered ring which contains a double bond and may optionally be interrupted by a further carbonyl group, a further thiocarbonyl group, an optionally substituted imino group and/or by one or more heteroatoms;
V is oxygen, sulphur or an optionally substituted nitrogen;
W is hydrogen or halogen;
X, Y and Z, each independently,
are hydrogen, halogen, hydroxyl, amino, cyano, nitro, OCN, SCN, SF 5 ; or
are trialkylsilyl, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxycarbonylalkyl, alkoxyalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, alkoxy, haloalkoxy, cyanoalkoxy, hydroxycarbonylalkoxy, alkoxycarbonylalkoxy, alkoxyalkoxy, alkylhydroxyimino, alkoxyimino, alkylalkoxyimino, haloalkylalkoxyimino, alkylthio, haloalkylthio, alkoxyalkylthio, alkylthioalkyl, alkylsulphinyl, haloalkylsulphinyl, alkoxyalkylsulphinyl, alkylsulphinylalkyl, alkylsulphonyl, haloalkylsulphonyl, alkoxyalkylsulphonyl, alkylsulphonylalkyl, alkylsulphonyloxy, alkylcarbonyl, haloalkylcarbonyl, carboxyl, alkylcarbonyloxy, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, cycloalkylaminocarbonyl, alkylsulphonylamino, aminosulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl, alkylsulphoximino, aminothiocarbonyl, alkylaminothiocarbonyl or dialkylaminothiocarbonyl, where all the aforementioned radicals may optionally be substituted; or
are phenylalkyl, phenoxy, phenylalkyloxy, phenoxyalkyl, phenylthio, phenylthioalkyl, phenylsulphinyl, phenylsulphonyl, hetaryl alkyl, hetaryloxy, hetarylalkyloxy, hetarylthio, hetarylsulphinyl or hetarylsulphonyl, where all the aforementioned radicals may optionally be substituted; or
are cycloalkylalkyl, cycloalkyloxy, cycloalkyl alkoxy, cycloalkylthio, cycloalkylalkylthio, cycloalkylsulphinyl, cycloalkylalkylsulphinyl, cycloalkylsulphonyl, cycloalkylalkylsulphonyl or cycloalkenyl, where all the aforementioned radicals may each optionally be substituted; or
are NR′R″
where R′ and R″ each independently
are hydrogen, cyano, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, acyl or alkoxycarbonyl; or
R′ and R″ together with the nitrogen atom to which they are bonded may form an optionally substituted, saturated or unsaturated five- to eight-membered ring optionally interrupted by one or more heteroatoms which are selected independently from the group consisting of O, S and N; or
are a 3- to 6-membered saturated, partly saturated or aromatic ring which may optionally contain one to three heteroatoms which are selected independently from the group consisting of O, S and N, and which may optionally be substituted;

 or X and Z, or Y and Z, together with the carbon atoms to which they are bonded, form a 5- or 6-membered ring which is optionally substituted and optionally interrupted by one or more heteroatoms which are selected independently from the group consisting of O, S, N and CO;
n is the number 0, 1 or 2.

2 . Compound according to claim 1 in which
A and B together with the atoms to which they are bonded are a substructure selected from the group consisting of

where
R 1 is hydrogen, cyano or nitro; or
is alkyl, cycloalkylalkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkoxycarbonylalkyl, alkylsulphanylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, haloalkylsulphanylalkyl, haloalkylsulphinylalkyl, haloalkylsulphonylalkyl, alkoxyalkylsulphanylalkyl, alkoxyalkylsulphinylalkyl, alkoxyalkylsulphonylalkyl, phenylalkyl, phenoxyalkyl, phenylsulphanylalkyl, phenylsulphinylalkyl, phenylsulphonylalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted; or
is optionally substituted saturated or unsaturated cycloalkyl which may optionally be interrupted by one or more heteroatoms; or
is alkylcarbonyl, haloalkylcarbonyl, hydroxyalkylcarbonyl, alkoxyalkylcarbonyl, phenylcarbonyl, hetarylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, dicycloalkylaminocarbonyl, cycloalkyl(alkyl)aminocarbonyl, arylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, cycloalkyl(aryl)aminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl or aminothiocarbonyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or is carbonyl or carboxyl; or
is optionally substituted phenyl or optionally substituted hetaryl; or
is alkoxy, haloalkoxy, cycloalkyloxy, aryloxy, arylalkyloxy or carbonyloxy, where the aforementioned radicals may optionally be substituted, or is hydroxyl; or
is alkylamino, haloalkylamino, dihaloalkylamino, dialkylamino, cycloalkylamino, dicycloalkylamino, cycloalkyl(alkyl)amino, arylamino, diarylamino, hetarylamino, dihetarylamino, alkyl(aryl)amino, cycloalkyl(aryl)amino, alkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, aryloxycarbonylamino, alkylcarbamoylamino, arylcarbamoylamino, alkylsulphonylamino, or arylsulphonylamino, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or is amino; or
is alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphanyl, cycloalkylsulphanyl, cycloalkylsulphinyl, cycloalkylsulphonyl, cycloalkylalkylsulphanyl, cycloalkylalkylsulphinyl, cycloalkylalkylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, aryl alkylsulphanyl, arylalkylsulphinyl, arylalkylsulphonyl, aminosulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl or arylaminosulphonyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or is sulphanyl; and

R 2 , R 3 , R 4 and R 5 each independently
are hydrogen, cyano, halogen or nitro; or
are alkyl, cycloalkylalkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkoxycarbonylalkyl, alkylsulphanylalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, haloalkylsulphanylalkyl, haloalkylsulphinylalkyl, haloalkylsulphonylalkyl, alkoxyalkylsulphanylalkyl, alkoxyalkylsulphinylalkyl, alkoxyalkylsulphonylalkyl, phenylalkyl, phenoxyalkyl, phenylsulphanylalkyl, phenylsulphinylalkyl, phenylsulphonylalkyl, hetarylalkyl, hetaryloxyalkyl, hetarylthioalkyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted; or
are optionally substituted saturated or unsaturated cycloalkyl which may optionally be interrupted by one or more heteroatoms; or
are alkylcarbonyl, haloalkylcarbonyl, hydroxyalkylcarbonyl, alkoxyalkylcarbonyl, phenylcarbonyl, hetarylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aryloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, cycloalkylaminocarbonyl, dicycloalkylaminocarbonyl, cycloalkyl(alkyl)aminocarbonyl, arylaminocarbonyl, diarylaminocarbonyl, alkyl(aryl)aminocarbonyl, cycloalkyl(aryl)aminocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl or aminothiocarbonyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or are carbonyl or carboxyl; or
are optionally substituted phenyl or optionally substituted hetaryl; or
are alkoxy, haloalkoxy, alkoxyalkoxy, aryloxy, arylalkyloxy, cycloalkyloxy, cycloalkylalkyloxy or carbonyloxy, where the aforementioned radicals may

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D207/273

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms · CPC title

• C07D271/113

  with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical · CPC title

• C07D277/42

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