Six-membered C-N-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest conrol agents

Patent metadata

Field	Value
Publication number	US-9783509-B2
Application number	US-201414903426-A
Country	US
Kind code	B2
Filing date	Jul 4, 2014
Priority date	Jul 8, 2013
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

The present invention relates to novel heterocyclic compounds, to processes for preparation thereof and to the use thereof for controlling animal pests, which include arthropods and especially insects and acarids.

First claim

The invention claimed is:

1. A compound of formula (I)

wherein
D is a substructure of formula (I-A)

 in which the ring nitrogen of substructure D is bonded to the six-membered ring in formula (I) and the arrow represents the bond to the six-membered ring;
V 1 and V 2 are each independently oxygen or N—R 11 ;
Q 1 is N—R 1 ;
Q 3 is CR 4 or nitrogen;
Q 4 is CR 5 or nitrogen;
R 1 is hydrogen;
or is (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl(C 1 -C 3 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, halo(C 1 -C 6 )alkyl, cyano(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, phenyl(C 1 -C 3 )alkyl or pyridyl(C 1 -C 3 )alkyl, where the aforementioned radicals are each optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphanyl, (C 1 -C 6 )alkylsulphonyl, halo(C 1 -C 6 )alkylsulphinyl, halo(C 1 -C 6 )alkylsulphanyl, halo(C 1 -C 6 )alkylsulphonyl or optionally methyl-, fluorine-, chlorine-, or cyano-substituted cyclopropyl, and where the nitrogen atom present in pyridyl(C 1 -C 3 )alkyl is optionally in the form of the N-oxide;
or is (C 3 -C 6 )cycloalkyl, (C 3 -C 6 )cycloalkenyl, azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, thiethanyl, thiolanyl, thianyl, phenyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiazadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, or triazolyl, where the aforementioned radicals are each optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphanyl, (C 1 -C 6 )alkylsulphonyl, halo(C 1 -C 6 )alkylsulphinyl, halo(C 1 -C 6 )alkylsulphanyl, halo(C 1 -C 6 )alkylsulphonyl or optionally methyl-, fluorine-, chlorine-, or cyano-substituted cyclopropyl, and where the nitrogen atom present in pyridyl is optionally in the form of the N-oxide;

R 4 and R 5 are each independently hydrogen, halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, cyano(C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, cyano or carboxyl;
R 11 is hydrogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, cyano(C 1 -C 6 )alkyl or (C 3 -C 6 )cycloalkyl;
W is hydrogen or fluorine;
n is 0 or 1;
X and Y are each independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyano, amino, hydroxyl or nitro; and
Z is hydrogen.

2. The compound according to claim 1 wherein
D is a substructure of the formula (I-A);
V 1 and V 2 are each independently oxygen;
Q 1 is N—R 1 ;
Q 3 is CR 4 ;
Q 4 is CR 5 or nitrogen;
R 1 is hydrogen, methyl, ethyl, n-propyl, CH(CH 3 ) 2 , n-butyl, sec-butyl, C(CH 3 ) 3 , CH 2 C(CH 3 ) 3 , CH 2 CH(CH 3 ) 2 , CH 2 CH═CH 2 , CH 2 CCH, cyclopropylmethyl, trifluoroethyl, 2,2-difluoroethyl, CH 2 CN, CH 2 OCH 3 , CH 2 CH 2 OCH 3 , benzyl, cyclopropyl, cyclobutyl, phenyl, 2-fluorophenylmethyl, 3-fluorophenylmethyl, 4-fluorophenylmethyl, 2-pyridylmethyl, N-oxide-2-pyridylmethyl, 3-pyridylmethyl, N-oxide-3-pyridylmethyl, 4-pyridylmethyl or N-oxide-4-pyridylmethyl;
R 4 and R 5 are each independently hydrogen, methyl, ethyl, tert-butyl, trifluoromethyl, methoxy, trifluoromethoxy, cyclopropyl, cyano or carboxyl;
W is hydrogen or fluorine;
n is 0 or 1;
X is hydrogen, chlorine, fluorine, methyl or ethyl;
Y is chlorine, bromine, cyano, methyl, ethyl, trifluoromethyl, fluorine or methoxy; and
Z is hydrogen.

3. The compound according to claim 1 , wherein
D is a substructure which is selected from the group consisting of

V 1 and V 2 are each independently oxygen or N—R 11 ;
R 1 is hydrogen;
or is (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl(C 1 -C 3 )alkyl, halo(C 1 -C 6 )alkyl, cyano(C 1 -C 6 )alkyl, hydroxyalkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, phenyl(C 1 -C 3 )alkyl, or pyridyl-(C 1 -C 3 )alkyl, where the aforementioned radicals are optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphanyl, (C 1 -C 6 )alkylsulphonyl, halo(C 1 -C 6 )alkylsulphinyl, halo(C 1 -C 6 )alkylsulphanyl, halo(C 1 -C 6 )alkylsulphonyl or optionally methyl-, fluorine-, chlorine-, or cyano-substituted cyclopropyl, and where one of the nitrogen atoms present in pyridyl(C 1 -C 3 )alkyl is optionally in the form of the N-oxide;
or is (C 3 -C 6 )cycloalkyl or (C 3 -C 6 )cycloalkenyl, azetidinyl, azolidinyl, azinanyl, oxetanyl, oxolanyl, oxanyl, thiethanyl, thiolanyl, or thianyl;
or is phenyl that is optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo-(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphanyl, (C 1 -C 6 )alkylsulphonyl, halo(C 1 -C 6 )alkylsulphinyl, halo(C 1 -C 6 )alkylsulphanyl, halo(C 1 -C 6 )alkylsulphonyl or optionally methyl-, fluorine-, chlorine-, or cyano-substituted cyclopropyl, or is hetaryl selected from the group consisting of pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, triazinyl, thiazolyl, thiazadiazolyl, oxazolyl, oxadiazolyl, pyrazolyl, and triazolyl, where the hetaryl is optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkoxy, (C 1 -C 6 )alkylsulphinyl, (C 1 -C 6 )alkylsulphanyl, (C 1 -C 6 )alkylsulphonyl, halo(C 1 -C 6 )alkylsulphinyl, halo(C 1 -C 6 )alkylsulphanyl, halo-(C 1 -C 6 )alkylsulphonyl or optionally methyl-, fluorine-, chlorine-, or cyano-substituted cyclopropyl, and where one of the nitrogen atoms present in hetaryl is optionally in the form of the N-oxide;

R 4 and R 5 are each independently hydrogen, halogen, cyano, (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkyl, cyano(C 1 -C 6 )alkyl, or carboxyl;
R 11 is hydrogen, (C 1 -C 4 )alkyl, (C 3 -C 6 )cycloalkyl, (C 1 -C 4 )haloalkyl, or cyano(C 1 -C 6 )alkyl;
W is hydrogen or fluorine;
n is 0 or 1; and
X and Y are each independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, trifluoromethoxy or cyclopropyl; and
Z is hydrogen.

4. The compound according to claim 3 , wherein D is a substructure of the formula (I-A-I).

5. The compound according to claim 3 , wherein D is a substructure of the formula (I-A-II).

6. The compound according to claim 3 , wherein D is a substructure of the formula (I-A-III).

7. The compound according to claim 1 , wherein D is a substructure of the formula (I-A-1)

in which
R 1 is hydrogen;
or is (C 1 -C 6 )alkyl, (C 3 -C 8 )cycloalkyl(C 1 -C 3 )alkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, halo(C 1 -C 6 )alkyl, cyano(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl, phenyl(C 1 -C 3 )alkyl or pyridyl(C 1 -C 3 )alkyl, where the aforementioned radicals are each optionally mono- to trisubstituted by halogen, cyano, nitro, hydroxyl, amino, (C 1 -C 6 )alkyl, halo-(C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6

Assignees

• Bayer Cropscience Ag

Inventors

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

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D251/20

  with no nitrogen atoms directly attached to a ring carbon atom · CPC title

• C07D253/075 Primary

  Two hetero atoms, in positions 3 and 5 · CPC title

• C07D239/557

  with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. orotic acid · CPC title