N-arylamidine-substituted trifluoroethyl sulfide derivatives as acaricides and insecticides

Patent metadata

Field	Value
Publication number	US-9642363-B2
Application number	US-201214366715-A
Country	US
Kind code	B2
Filing date	Dec 12, 2012
Priority date	Dec 21, 2011
Publication date	May 9, 2017
Grant date	May 9, 2017

Abstract

The present invention relates to novel N-arylamide-substituted trifluoroethyl sulfide derivatives of the formula (I)

in which X 1 , X 2 , X 3 , X 4 , R 1 , R 2 , R 3 , n have the meanings given in the description—to their use as acaricides and insecticides for controlling animal pests and to processes and intermediates for their preparation.

First claim

The invention claimed is:

1. An N-arylamidine-substituted trifluoroethyl sulfide derivative of formula (I)

in which
n represents the number 0, 1 or 2,
X 1 , X 2 , X 3 , X 4 independently of one another represent hydrogen, halogen, hydroxy, amino, OCN, SCN, SF 5 , 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, alkoxycarbonylalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkenylaminocarbonyl, dialkenylaminocarbonyl, cycloalkylaminocarbonyl, alkyl sulfonylamino, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, alkylsulfoximino, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl,
or represent optionally substituted phenylalkyl, phenoxy, phenylalkyloxy, phenoxyalkyl, phenylthio, phenylthioalkyl, phenylsulfinyl, phenylsulfonyl, hetarylalkyl, hetaryloxy, hetarylalkyloxy, hetarylthio, hetarylsulfinyl, hetarylsulfonyl,
or represent optionally substituted saturated or unsaturated cycloalkylalkyl, cycloalkyloxy, cycloalkylalkoxy, cycloalkylthio, cycloalkylalkylthio, cycloalkylsulfinyl, cycloalkylalkylsulfinyl, cycloalkylsulfonyl, cycloalkylalkylsulfonyl,
or represent NR 4 R 5 , where R 4 and R 5 independently of one another represent hydrogen, cyano, alkyl, haloalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, acyl, alkoxycarbonyl, or R 4 and R 5 together with the nitrogen atom to which they are attached may form an optionally substituted saturated or unsaturated five- to eight-membered ring which is optionally interrupted by heteroatoms from the group consisting of O, S and N,
or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N,
or X 2 and X 3 or X 3 and X 4 , form, together with the carbon atoms to which they are attached, a 5- or 6-membered ring which is optionally substituted and optionally interrupted by heteroatoms from the group consisting of O, S, N and CO,
R 3 represents alkoxyalkul, cyanoalkyl, alkylthioalkyl, haloalkenyl, alkynyl, haloalkynyl,
or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcabonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N,
or represents a 3- to 6-membered aromatic ring which contains one to three heteroatoms from the group consisting of O, S and N and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkyl sulfinyl, alkylsulfonyl, alkyl sulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcabonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N,
R 1 and R 2 independently of one another represent hydrogen, cyano, alkyl, haloalkyl, alkoxy, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkylthioalkyl, alkenyl, haloalkenyl, cyanoalkenyl, alkynyl, haloalkynyl, cyanoalkynyl, represent optionally substituted alkylcarbonyl, alkoxycarbonyl, arylcarbonyl, hetarylcarbonyl, aryloxycarbonyl, hetaryloxycarbonyl, alkylsulfinyl, haloalkylsulfinyl, arylsulfinyl, arylalkylsulfinyl, hetarylsulfinyl, hetarylalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, arylsulfonyl, arylalkylsulfonyl, hetarylsulfonyl, hetarylalkylsulfonyl,
or represent a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by C═O, SO or SO 2 and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, haloalkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylsulfonyloxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkoxycarbonyl, alkylcarbonyl, alkylcarbonyloxy, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, aminothiocarbonyl, alkylaminothiocarbonyl, dialkylaminothiocarbonyl, cycloalkylamino, alkylsulfonylamino, aminosulfonyl, alkylaminosulfonyl and dialkylaminosulfonyl, or by optionally substituted cycloalkyl, cycloalkoxy, cycloalkylalkyl or cycloalkylalkoxy which are optionally interrupted by heteroatoms from the group consisting of O, S and N,
or represent —(CH 2 ) m —R 6 , —O—(CH 2 ) m —R 6 , —(CH 2 ) m —O—R 6 , where R 6 represents a 3- to 6-membered saturated, partially saturated or aromatic ring which may optionally contain one to three heteroatoms from the group consisting of O, S and N, which may optionally be interrupted once or twice by C═O and which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, hydroxy, amino, carboxy, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl,

Assignees

• Bayer Cropscience Ag
• Bayer Ip Gmbh

Inventors

• Koehler Adeline
• Alig Bernd
• Becker Angela
• Voerste Arnd
• Goergens Ulrich
• Fischer Reiner
• Moradi Wahed Ahmed
• Cerezo-Galvez Silvia
• Hahn Julia Johanna
• Ilg Kerstin
• Schwarz Hans-Georg
• Gomibuchi Takuya
• Ito Masahito
• Yamazaki Daiei
• Shibuya Katsuhiko
• Shimojo Eiichi

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• C07D279/06

  not condensed with other rings · CPC title

• C07C317/40

  Y being a hydrogen or a carbon atom · CPC title

• C07C317/34

  having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring · CPC title

• C07D295/125

  with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings · CPC title