Five-membered C-N-attached aryl sulphide and aryl sulphoxide derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-10206398-B2
Application number	US-201515533565-A
Country	US
Kind code	B2
Filing date	Dec 8, 2015
Priority date	Dec 11, 2014
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

Provided are compounds of the formula (I)

which are suitable for controlling animal pests including arthropods and in particular insects and acarids and in which the structural elements have the meanings given in the description.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
W represents hydrogen or halogen;
n represents the number 0, 1 or 2;
Y represents hydrogen, halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy or amino; or
represents NR′″R″″, where R′″ and R″″ independently of one another represent hydrogen, (C 1 -C 6 ) alkyl or halo-(C 2 -C 6 )-alkyl;

X represents hydrogen, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl or (C 1 -C 6 )-alkoxy;
V 1 and V 2 independently of one another represent oxygen or sulphur;
R 1 and R 2 independently of one another
represent hydrogen, halogen, hydroxy, cyano or nitro; or
represent alkyl, alkenyl, alkynyl, alkoxy, alkylsulphanyl, alkylsulphinyl, alkylsulphonyl, haloalkylcarbonyl, alkylcarbonyl or alkoxycarbonyl, where the radicals mentioned above may optionally be substituted by halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy; or

R 1 and R 2 together form a saturated or unsaturated three- to six-membered ring which is optionally substituted by halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, and optionally interrupted by one or more heteroatoms independently selected from the group consisting of O, S and N, with the proviso that two oxygen atoms are not directly adjacent to one another;
R 3 represents alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkyl-S(O) m -alkyl, haloalkyl-S(O) m -alkyl, N-alkylaminocarbonylalkyl or N,N-dialkylaminocarbonylalkyl, or
represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl, or
represents heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl;

R 4 represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, haloalkoxyalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkyl-S(O) m -alkyl, haloalkyl-S(O) m -alkyl, N-alkylaminocarbonylalkyl or N,N-dialkylaminocarbonylalkyl, or
represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl, or
represents heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl; or

R 3 and R 4 together with the nitrogen atom to which they are attached form a saturated to triunsaturated 3- to 6-membered ring selected from the group consisting of aziridinyl, azirenyl, diaziridinyl, diazirenyl, azetidinyl, dihydroazetyl, diazetidinyl, dihydrodiazetyl, oxazetidinyl, oxazetyl, thiazetidinyl, thiazetyl, pyrrolidinyl, dihydropyrrolyl, pyrazolidinyl, dihydropyrazolyl, imidazolidinyl, dihydroimidazolyl, oxazolidinyl, dihydrooxazolyl, thiazolidinyl, dihydrothyazolyl, piperidinyl, piperazinyl, hexahydropyridazinyl, hexahydropyrimidinyl, morpholine, dioxazinanyl, thiomorpholine, dithiazinane, dioxothiazinane, pyrrolyl, pyrazolyl, imidazolyl, triazolyl and tetrazolyl which is optionally substituted by halogen, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy or (C 3 -C 6 )-cycloalkyl; and
m represents the number 0, 1 or 2.

2. The compound according to claim 1 wherein
W represents hydrogen or halogen;
n represents the number 0 or 1;
Y represents hydrogen, halogen, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkoxy or amino; or
represents NR′″ R″″, where R′″ and R″″ independently of one another represent hydrogen, (C 1 -C 4 )-alkyl or (C 2 -C 4 )-haloalkyl;

X represents hydrogen, halogen, cyano, (C 1 -C 3 )-alkyl, (C 1 -C 3 )-haloalkyl or (C 1 -C 3 )-alkoxy;
V 1 and V 2 independently of one another represent oxygen or sulphur;
R 1 and R 2 independently of one another represent hydrogen or (C 1 -C 3 )-alkyl; or
R 1 and R 2 together with the carbon atom to which they are attached represent a (C 3 -C 6 )-cycloalkyl ring;
R 3 represents (C 1 -C 6 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, (C 1 -C 6 )-alkenyl, halo-(C 1 -C 3 )-alkenyl, (C 1 -C 6 )-alkynyl, halo-(C 1 -C 3 )-alkynyl, (C 1 -C 3 )-alkyl-S(O) m -(C 1 -C 3 )-alkyl, halo-(C 1 -C 3 )-alkyl-S(O) m -(C 1 -C 3 )-alkyl, N—(C 1 -C 3 )-alkylaminocarbonyl-(C 1 -C 3 )-alkyl or N,N-di-(C 1 -C 3 )-alkylaminocarbonyl-(C 1 -C 3 )-alkyl, or
represents (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl, (C 3 -C 6 )-cycloalkenyl or (C 3 -C 6 )-cycloalkenyl-(C 1 -C 3 )-alkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl, or
represents heterocyclyl, heterocyclyl-(C 1 -C 3 )-alkyl, aryl, aryl-(C 1 -C 3 )-alkyl, hetaryl or hetaryl-(C 1 -C 3 )-alkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl;

R 4 represents hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 3 )-alkyl or (C 1 -C 3 )-alkoxy-(C 1 -C 3 )-alkyl, or
represents (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl, phenyl, phenyl-(C 1 -C 3 )-alkyl, pyridyl or pyridyl-(C 1 -C 3 )-alkyl which is optionally mono- or disubstituted by identical or different substituents selected from the group consisting of halogen, cyano, nitro, hydroxy, amino, (C 1 -C 4 )-alkyl, halo-(C 1 -C 3 )-alkyl, (C 1 -C 3 )-alkoxy, halo-(C 1 -C 3 )-alkoxy and cyclopropyl; or

R 3 and R 4 together with the nitrogen atom to which they are attached form a saturated to triunsaturated 3- to 6-membered ring selected from the group consisting of aziridinyl, azirenyl, diaziridinyl, diazirenyl, azetidinyl, dihydroazetyl, diazetidinyl, dihydrodiazetyl, oxazetidinyl, oxazetyl, thiazetidinyl, thiazetyl, pyrrolidinyl, dihydropyrrolyl, pyrazolidinyl, dihydropyrazolyl, imidazolidinyl, dihydroimidazolyl, oxazolidinyl, dihydrooxazolyl, thiazolidinyl, dihydrothyazolyl, piperidinyl, piperazinyl, hexahydropyridazinyl, hexahydropyrimidinyl, morpholine, dioxazinanyl, thiomorpholine, dithiazinane, dioxothiazinane, pyrrolyl, pyrazolyl, imidazolyl, triazolyl and tetrazolyl which is optionally substituted by halogen, cyano, (C 1 -C 4 )-alkyl, halo-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, halo-(C 1 -C 4 )-alkoxy, (C 3 -C 6 )-cycloalkyl; and
m represents the number 0, 1 or 2.

3. The compound according to claim 1 wherein
W represents hydrogen or fluorine;
n represents the number 0 or 1;
Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or metho

Assignees

• Bayer Cropscience Ag

Inventors

• Cerezo-Galvez Silvia
• Alig Bernd
• Fischer Reiner
• Hahn Julia Johanna
• Harschneck Tobias
• Wilcke David
• Ilg Kerstin
• Malsam Olga
• Lösel Peter
• Köhler Adeline
• Portz Daniela
• Görgens Ulrich
• Eilmus Sascha

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/10

  Anthelmintics · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D233/80 Primary

  with hetero atoms or acyl radicals directly attached to ring nitrogen atoms · CPC title

• C07D233/56 Primary

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