Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides

Patent metadata

Field	Value
Publication number	US-9981928-B2
Application number	US-201414899260-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 sulfoxide derivatives, to the use thereof as acaricides and insecticides for controlling animal pests and to processes and intermediates for preparation thereof. The aryl sulfide and aryl sulfoxide 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 attached represent; a substructure selected from the group consisting of

wherein when substructure of formula (I-A), (I-B) or (I-D) is present then V 1 , V 2 and V 3 each independently of one another are oxygen; sulfur, an optionally substituted nitrogen or salts of an optionally substituted nitrogen; and
wherein when substructure of formula (I-C) is present then V 1 , V 2 and V 3

each independently of one another represent oxygen or sulfur,
Q 1 and Q 2 each independently of one another
represent oxygen, sulfur or an optionally substituted nitrogen; or
represent an optionally substituted carbon atom; with the proviso, that Q 1 does not represent an alkylcarbonylamino radical;
R 4 , R 5 , R 6 and R 7 each independently of one another
represent hydrogen, cyano, halogen or nitro; or

represent alkyl, cycloalkylalkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, aminoalkyl, alkoxycarbonylalkyl, alkylthioalkyl, haloalkylthioalkyl, alkoxyalkylthioalkyl, alkylsulfanylalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, haloalkylsulfanylalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkoxyalkylsulfanylalkyl, alkoxyalkylsulfinylalkyl, alkoxyalkylsulfonylalkyl, phenylalkyl, phenoxyalkyl, phenylsulfanylalkyl, phenylsulfinylalkyl, phenylsulfonylalkyl, hetarylalkyl, hetaryloxyalkyl or hetarylthioalkyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted; or
represent optionally substituted saturated or unsaturated cycloalkyl which may optionally be interrupted by one or more heteroatoms; or
represent 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 represent carbonyl or carboxyl; or
represent optionally substituted phenyl or optionally substituted hetaryl;
represent alkoxy, haloalkoxy, alkoxyalkoxy, aryloxy, arylalkyloxy, cycloalkyloxy, cycloalkylalkyloxy or carbonyloxy, where the aforementioned radicals may be saturated or unsaturated and/or optionally substituted, or represent hydroxyl; or
represent 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, alkylsulfonylamino, or arylsulfonylamino, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or represent amino; or
represent alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, haloalkylsulfanyl, haloalkylsulfinyl, haloalkylsulfonyl, cycloalkylsulfanyl, cycloalkylsulfinyl, cycloalkylsulfonyl, cycloalkylalkylsulfanyl, cycloalkylalkylsulfinyl, cycloalkylalkylsulfonyl, arylsulfanyl, arylsulfinyl, arylsulfonyl, arylalkylsulfanyl, arylalkylsulfinyl, arylalkylsulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl or arylaminosulfonyl, where the aforementioned radicals may each be saturated or unsaturated and/or optionally substituted, or represent sulfanyl; or
R 4 and R 5 together with the atom to which they are attached 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 6 and R 7 together with the atom to which they are attached 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;
W represents hydrogen or halogen;
V represents oxygen; sulfur, an optionally substituted nitrogen or salts of an optionally substituted nitrogen;
X, Y and Z each independently of one another
represent hydrogen, halogen, hydroxyl, amino, cyano, nitro, OCN, SCN, SF 5 ; or
represent 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, alkylsulfinyl, haloalkylsulfinyl, alkoxyalkylsulfinyl, alkylsulfinylalkyl, alkylsulfonyl, haloalkylsulfonyl, alkoxyalkylsulfonyl, alkylsulfonylalkyl, alkylsulfonyloxy, alkylcarbonyl, haloalkylcarbonyl, carboxyl, alkylcarbonyloxy, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, cycloalkylaminocarbonyl, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfoximino, aminothiocarbonyl, alkylaminothiocarbonyl or dialkylaminothiocarbonyl, where all the aforementioned radicals may optionally be substituted; or
represent phenylalkyl, phenoxy, phenylalkyloxy, phenoxyalkyl, phenylthio, phenylthioalkyl, phenylsulfinyl, phenylsulfonyl, hetarylalkyl, hetaryloxy, hetarylalkyloxy, hetarylthio, hetarylsulfinyl or hetarylsulfonyl, where all the aforementioned radicals may optionally be substituted; or
represent cycloalkylalkyl, cycloalkyloxy, cycloalkylalkoxy, cycloalkylthio, cycloalkylalkylthio, cycloalkylsulfinyl, cycloalkylalkylsulfinyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl or cycloalkenyl, where all the aforementioned radicals may each optionally be substituted; or
represent NR′R″,
where R′ and R″ each independently of one another
represent 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 attached 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
represent 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 attached, 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; and

n represents the number 0, 1 or 2.

2. The compound as claimed in claim 1 in which
A and B together with the atoms to which they are attached represent a substructure selected from the group consisting of (I-A) to (I-D),
wherein when substructure of formula (I-A), (I-B) or (I-D) is present then

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

• C07D263/44

  Two oxygen atoms · CPC title

• C07D233/32

  One oxygen atom · CPC title

• C07D249/12

  Oxygen or sulfur atoms · CPC title

• C07D233/34

  Ethylene-urea · CPC title

• C07D233/74

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members · CPC title