Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides

Patent metadata

Field	Value
Publication number	US-9981940-B2
Application number	US-201414899259-A
Country	US
Kind code	B2
Filing date	Jun 16, 2014
Priority date	Jun 20, 2013
Publication date	May 29, 2018
Grant date	May 29, 2018

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

The invention claimed is:

1. A compound of formula (I)

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, alkoxyalkylsulphonylalkyl, 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, arylalkylsulphanyl, 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, alkoxyalkylsulphonylalkyl, 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, di arylaminoc arbonyl, 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 be saturated or unsaturated and/or optionally substituted, or are hydroxyl; or
are alkylamino, dialkylamino, haloalkylamino, dihaloalkylamino, 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 are amino; or
are alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylsulphanyl, haloalkylsulphinyl, haloalkylsulphonyl, cycloalkylsulphanyl, cycloalkylsulphinyl, cycloalkylsulphonyl, cycloalkylalkylsulphanyl, cycloalkylalkylsulphinyl, cycloalkylalkylsulphonyl, arylsulphanyl, arylsulphinyl, arylsulphonyl, arylalkylsulphanyl, arylalkylsulphinyl, arylalkylsulphonyl, aminosulphonyl, alkylaminosulphonyl, dialkylaminosulphonyl or arylaminosulphonyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or are sulphanyl; or
R 4 and R 5 together with the atom to which they are bonded may form an optionally substituted, saturated or unsaturated three- 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
R 2 is a saturated or unsaturated cycle optionally interrupted by one or more heteroatoms which are each selected from the group consisting of O, S and N, which may optionally be substituted;
where in substructures of formula (I-B), (I-C), (I-D), (I-E), (I-F) or (I-G) V and V′ are each independently oxygen, sulphur or an optionally substituted nitrogen; and
wherein in substructure of formula (I-A), V and V′ each independently are oxygen or sulphur,

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, phenylalk

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

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P43/00

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

• C07D207/408

  Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms · CPC title

• A01N43/78

  1,3-Thiazoles; Hydrogenated 1,3-thiazoles · CPC title