Aryl-triazolyl pyridines as pest control agents

Patent metadata

Field	Value
Publication number	US-10208015-B2
Application number	US-201515325665-A
Country	US
Kind code	B2
Filing date	Jul 13, 2015
Priority date	Jul 15, 2014
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

The invention relates to novel aryltriazolylpyridines of the general formula (I). Also described are processes for preparing the compounds of the formula (I). The compounds according to the invention are especially suitable for controlling insects and arachnids in agriculture, and ectoparasites in veterinary medicine.

First claim

The invention claimed is:

1. Compound of formula (I)

in which
R 1 represents hydrogen, unsubstituted or cyano-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, or aryl-C 1 -C 6 -alkyl;
the chemical moieties
A 1 represents CR 2 ,
A 2 represents nitrogen,
A 3 represents CR 3 ,
A 4 represents CR 4 ,
B 1 represents CR 5 ,
B 2 represents CR 6 ,
B 3 represents CR 7 ,
B 4 represents CR 8 , and
B 5 represents CR 9 ,
R 2 , R 3 , R 4 , R 5 , R 6 , R 8 and R 9 independently of one another represent hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted C 1 -C 6 -alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 -alkoxy, N—(C 1 -C 6 -alkoxy)imino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—(C 1 -C 6 -alkyl)amino or NN-di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylsulphonylamino, N—(C 1 -C 6 -alkyl)-C 1 -C 6 -alkylsulphonylamino, or phenyl;
R 7 represents halogen, cyano, nitro, in each case optionally halogen-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N—C 1 -C 6 -alkoxyimino-C 1 -C 3 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino or phenyl;
R 10 independently of one another represents hydrogen, halogen, cyano, nitro, amino or optionally halogen-substituted C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, or C 1 -C 6 -alkylsulphonyl;
W represents oxygen or sulphur;
Q represents hydrogen, formyl, hydroxy, amino, or one of the optionally halogen-substituted moieties C 1 -C 6 -alkyl, C 1 -C 6 -alkyloxy, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl, or aryl—C 1 -C 6 -alkyl or represents a moiety N—(C 1 -C 6 -alkyl)amino, N—(C 1 -C 6 -alkylcarbonyl)amino, or N,N-di(C 1 -C 6 -alkyl)amino; or
Q represents an unsaturated 6-membered carbocycle which is optionally polysubstituted by V, where
V represents halogen, cyano, nitro, or one of the moieties C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkoxy, N—(C 1 -C 6 -alkoxy)imino-C 1 -C 6 -alkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, or N,N-di(C 1 -C 6 -alkyl)amino;
and/or a salt, N-oxide and/or a tautomeric form of a compound of the formula (I).

2. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
R 1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, 2-propyn-1-yl, 2-propen-1-yl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, or 4-methoxybenzyl;
the chemical moieties
A 1 represents CR 2 ,
A 2 represents nitrogen,
A 3 represents CR 3 ,
A 4 represents CR 4 ,
B 1 represents CR 5 ,
B 2 represents CR 6 ,
B 3 represents CR 7 ,
B 4 represents CR 8 , and
B 5 represents CR 9 ,
R 2 and R 4 independently of one another represent hydrogen, methyl, fluorine or chlorine; and
R 3 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1 -methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl, trifluoromethylsulphanyl, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N-diethylamino, methyl sulphonylamino, or N-methylmethylsulphonylamino;
R 5 , R 6 , R 8 and R 9 independently of one another represent hydrogen, halogen, cyano, nitro, methyl, ethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methyl sulphanyl, trifluoromethylsulphanyl, methylsulphonyl, methyl sulphinyl, trifluoromethylsulphonyl, or trifluoromethylsulphinyl, but where R 6 and R 10 do not simultaneously represent hydrogen,
R 7 represents perhalogenated C 1 -C 6 -alkyl, perhalogenated C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, N-alkoxyiminoalkyl, C 1 -C 6 -alkylsulphanyl, C 1 -C 6 -alkylsulphinyl, C 1 -C 6 -alkylsulphonyl, N—C 1 -C 6 -alkylamino, N,N-di-C 1 -C 6 -alkylamino, and also represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, chloromethyl, bromomethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2- trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, nonafluoro-sec-butyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1-(N-methoxyimino)ethyl, methylsulphanyl, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl, trifluoromethylsulphinyl, trifluoromethylsulphanyl, N,N-dimethylamino, or phenyl;
10 independently of one another represents hydrogen, halogen, cyano, nitro, amino, methyl, ethyl, 1-methylethyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methylcarbonyl, ethylcarbonyl, trifluoromethylcarbonyl, methylsulphanyl, methylsulphinyl, methylsulphonyl, trifluoromethylsulphonyl, trifluoromethylsulphanyl, or trifluoromethylsulphinyl;
W represents oxygen or sulphur;
Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, 1-methylpropyl, n-butyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1-cyanocyclopropyl, 1-methoxycarbonylcyclopropyl, 1-(N-methylcarbamoyl)cyclopropyl, 1-(N-cyclopropylcarbamoyl)cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropyl ethyl, bis(cyclopropyl)methyl, 2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-ynyl, 1,1-dimethylbut-2-ynyl, 3-chloroprop-2-enyl, 3,3 -dichloroprop-2-enyl, 3, 3-dichloro-1,1 -dimethylprop-2-enyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluoromethylphenylethyl, 2-ethoxyethyl, 2-(methylsulphanyl)ethyl, 1-methyl-2-(ethylsulphanyl)ethyl, 2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl, methoxyca

Assignees

• Bayer Animal Health Gmbh

Inventors

• Hallenbach Werner
• Schwarz Hans-Georg
• Goergens Ulrich
• Ilg Kerstin
• Turberg Andreas
• Horstmann Sebastian
• Koehler Adeline

Classifications

• A61P33/14

  Ectoparasiticides, e.g. scabicides · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/647

  Triazoles; Hydrogenated triazoles · CPC title