Six-membered C—N-bonded aryl sulphide and aryl sulphoxide derivatives as pesticides

Patent metadata

Field	Value
Publication number	US-10039282-B2
Application number	US-201415104004-A
Country	US
Kind code	B2
Filing date	Dec 12, 2014
Priority date	Dec 16, 2013
Publication date	Aug 7, 2018
Grant date	Aug 7, 2018

Abstract

Illustrated are compounds of the formula (I), which are suitable for controlling animal pests including arthropods and in particular insects and acarids

in which the structural elements have the meanings given in the description.

First claim

The invention claimed is:

1. Compound of the formula (I),

in which
V represents oxygen;
Q represents C—R 5 , where
R 5 represents hydrogen, halogen, amino, cyano, nitro, (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 1 -C 6 )-alkylsulphanyl, (C 1 -C 6 )-alkylsulphinyl, (C 1 -C 6 )-alkylsulphonyl, (C 1 -C 6 )-haloalkylsulphanyl, (C 1 -C 6 )-haloalkylsulphinyl, (C 1 -C 6 )-haloalkylsulphonyl, (C 3 -C 6 )-cycloalkyl or (C 1 -C 6 )-alkoxy;

R 3 and R 6 independently of one another
represent hydrogen, halogen, cyano or nitro; or
represent (C 1 -C 6 )-alkyl, (C 1 -C 6 )-haloalkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-haloalkoxy, (C 1 -C 6 )-haloalkylsulphanyl, (C 1 -C 6 )-haloalkylsulphinyl, (C 1 -C 6 )-haloalkylsulphonyl, (C 1 -C 6 )-alkylsulphanyl, (C 1 -C 6 )-alkylsulphinyl, (C 1 -C 6 )-alkylsulphonyl, (C 1 -C 5 )-alkylcarbonyl, (C 1 -C 5 )-haloalkylcarbonyl or (C 2 -C 6 )-alkoxycarbonyl; or
represent (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 3 )-alkyl or (C 3 -C 6 )-cycloalkenyl, where the radicals mentioned above may optionally be substituted by halogen, alkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy; or
represent phenyl, heteroaryl, phenyl-(C 1 -C 3 )-alkyl or heteroaryl-(C 1 -C 3 )-alkyl, where the radicals mentioned above may optionally be substituted by halogen, alkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy; or

represent NR′R″,
where R′ and R″ independently of one another represent hydrogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-cyanoalkyl, (C 1 -C 4 )-hydroxyalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphanyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphonyl-(C 1 -C 4 )-alkyl, (C 3 -C 4 )-alkenyl, (C 3 -C 4 )-haloalkenyl, (C 2 -C 4 )-cyanoalkenyl, (C 3 -C 4 )-alkynyl, (C 3 -C 4 )-haloalkynyl, (C 3 -C 4 )-cyanoalkynyl, (C 1 -C 4 )-alkylcarbonyl or (C 1 -C 4 )-alkoxycarbonyl;
or
where R′ and R″ together with the nitrogen atom to which they are attached may form an optionally halogen-, alkyl-, cyano-, nitro-, alkoxy-, haloalkyl- or haloalkoxy-substituted, saturated or unsaturated three- to eight-membered ring 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 must not be directly adjacent to one another; or

W represents hydrogen or halogen;
n represents the number 0 or 1;
Y represents halogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy, (C 1 -C 4 )-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 halogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl or (C 1 -C 4 )-alkoxy.

2. Compound according to claim 1 , in which
Q represents C—R 5 , where
R 5 represents hydrogen, halogen, amino, cyano, nitro, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 3 -C 6 )-cycloalkyl or (C 1 -C 4 )-alkoxy;
R 3 and R 6 independently of one another
represent hydrogen or halogen; or
represent (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-alkoxy or (C 1 -C 4 )-haloalkoxy; or
represent (C 3 -C 6 )-cycloalkyl or (C 3 -C 6 )-cycloalkyl-(C 1 -C 2 )-alkyl, where the radicals mentioned above may optionally be substituted by fluorine, chlorine, bromine, iodine, (C 1 -C 3 )-alkyl, cyano, nitro, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkyl or (C 1 -C 3 )-haloalkoxy; or
represent phenyl or phenyl-(C 1 -C 3 )-alkyl, where the radicals mentioned above may optionally be mono- or disubstituted by fluorine, chlorine, bromine, iodine, (C 1 -C 3 )-alkyl, cyano, nitro, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkyl or (C 1 -C 3 )-haloalkoxy; or
represent heteroaryl selected from the group consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, indolyl, isoindolyl and indazolyl, where the radicals mentioned above may optionally be mono- or disubstituted by fluorine, chlorine, bromine, iodine, (C 1 -C 3 )-alkyl, cyano, nitro, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkyl or (C 1 -C 3 )-haloalkoxy; or

represent NR′R″,
where R′ and R″ independently of one another represent hydrogen, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-haloalkyl, (C 1 -C 4 )-cyanoalkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphanyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphinyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylsulphonyl-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkylcarbonyl or (C 1 -C 4 )-alkoxycarbonyl;
or
where R′ and R″ together with the nitrogen atom to which they are attached may form a saturated four- to six-membered ring which is optionally mono- or disubstituted by fluorine, chlorine, bromine, iodine, (C 1 -C 3 )-alkyl, cyano, nitro, (C 1 -C 3 )-alkoxy, (C 1 -C 3 )-haloalkyl or (C 1 -C 3 )-haloalkoxy and optionally interrupted by a heteroatom selected from the group consisting of O, S and N;

W represents hydrogen or fluorine;
Y represents fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, amino, methylamino or dimethylamino;
X represents fluorine, chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, methoxy or ethoxy.

3. Compound according to claim 1 , in which
Q represents C—R 5 , where
R 5 represents hydrogen, methyl, ethyl, methoxy, cyclopropyl or trifluoromethyl;
R 3 and R 6 independently of one another represent hydrogen, fluorine, methyl, ethyl, isopropyl, trifluoromethyl, pentafluoroethyl, difluoromethyl, 1,1-difluoroethyl, difluorochloromethyl, cyclopropyl or phenyl;
W represents hydrogen or fluorine;
Y represents fluorine, chlorine, bromine, methyl, or methoxy;
X represents chlorine, fluorine or methyl.

4. Compound according to claim 1 , in which
Q represents C—R 5 , where
R 5 represents hydrogen or methyl;
R 3 represents hydrogen, methyl, ethyl, cyclopropyl, isopropyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl or phenyl;
R 6 represents hydrogen, fluorine or methyl;
W represents fluorine;
Y represents bromine, chlorine or methyl;
X represents chlorine, fluorine or methyl.

5. Formulation, comprising at least one compound of the formula (I) according to claim 1 .

6. Formulation according to claim 5 , further comprising at least one extender and/or at least one surface-active substance.

7. Formulation according to claim 5 , wherein the compound of the formula (I) is in a mixture with at least one further active compound.

8. Method for controlling one or more pests, comprising allowing a compound of the formula (I) according to claim 1 to act on the pests and/or a habitat thereof, wherein the pests are selected from the group consisting of ticks, spider mites, beetles and southern root-knot nematodes.

9. Method for protecting seed or a germinating plant from pests, comprising contacting seed with a compound of the formula (I) according to claim 1 , wherein the pests are selected from the group consisting of ticks, spider mites, beetles and southern root-knot nematodes.

10. Seed obtained by a method according to claim 9 .

11. Compound according to claim 1 , in which
Q represents C—R 5 , where
R 5 represents hydrogen, methyl, ethyl,

Assignees

• Bayer Cropscience Ag

Inventors

• Köhler Adeline
• Cerezo-Galvez Silvia
• Alig Bernd
• Fischer Reiner
• HAHN Johanna Julia
• Ilg Kerstin
• Portz Daniela
• Malsam Olga
• Lösel Peter
• Wilcke David

Classifications

• A61P33/00

  Antiparasitic agents · CPC title

• A01N43/54 Primary

  1,3-Diazines; Hydrogenated 1,3-diazines · CPC title

• C07D239/36

  as doubly bound oxygen atom or as unsubstituted hydroxy radical · CPC title

• A01N43/707

  1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines · CPC title