Aryl-triazolyl pyridines as pest control agents
View Patent ↗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.
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, methoxycarbonylmethyl, NH 2 , N-ethylamino, N-allylamino, N,N-dimethylamino, N,N-diethylamino, or 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl; or
Q represents phenyl or naphthyl substituted by 0 -4 substituents V, where
V independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, 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, 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, or N,N-dimethylamino.
3. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric 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 CH,
A 2 represents nitrogen,
A 3 represents CR 3 , and
A 4 represents CH;
B 1 represents CR 5 ,
B 2 represents CH,
B 3 represents CR 7 ,
B 4 represents CR 8 , and
B 5 represents CR 9 ,
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, methylsulphanyl, trifluoromethylsulphanyl, methylsulphonyl, methylsulphinyl, trifluoromethylsulphonyl, or trifluoromethylsulphinyl, but where R 6 and R 10 do not simultaneously represent hydrogen;
R 7 represents difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 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, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, trifluoromethylsulphonyl, trifluoromethylsulphinyl, trifluoromethylsulphanyl, or phenyl;
R 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, methyl sulphinyl, methylsulphonyl, trifluoromethylsulphonyl, trifluoromethylsulphanyl, or trifluoromethylsulphinyl;
W represents oxygen; and
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-cyclopropylethyl, 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, methoxy, 2-ethoxyethyl, 2-(methylsulphanyl)ethyl, 1-methyl-2-(ethylsulphanyl)ethyl, 2-methyl-1-(methylsulphanyl)propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH 2 , N-ethylamino, N-allylamino, N,N-dimethylamino, N,N-diethylamino, or 2-oxo-2-(2,2,2-trifluoroethylamino)ethyl; or
Q represents phenyl or naphthyl substituted by 0 - 4 substituents V, where
V independently of one another represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, isopropyl, 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, 2chl oro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, pentafluoro-tert-butyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-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 1, trifluoromethylsulphonyl, trifluoromethylsulphinyl, trifluoromethylsulphanyl, or N,N-dimethylamino;
R 5 represents hydrogen, methyl, ethyl, 2-methylethyl, tert-butyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, difluoromethoxy, trifluoromethoxy, or amino.
4. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric according to claim 1 in which
W represents oxygen;
R 10 represents hydrogen and R 1 represents hydrogen or methyl;
B 3 represents CR 7 and R 7 represents perhalogenated C 1 -C 4 -alkyl; or
B 3 represents CR 7 and R 7 represents perhalogenated C 1 -C 4 -alkyl or phenyl;
Q represents cyclopropyl optionally substituted independently by F, Cl, Br, I or CN.
5. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric according to claim 1 in which
W represents oxygen;
R 10 represents hydrogen and R 1 represents hydrogen or methyl;
B 3 represents CR 7 and R 7 represents —C 3 F 7 ; or
B 3 represents CR 7 and F 7 represents —C 3 F 7 or phenyl; and
Q represents cyclopropyl or 1-cyanocyclopropyl.
6. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
B 1 represents CR 5 , and R 5 represents halogen, C 1 -C 6 -alkoxy or C 1 -C 6 -alkyl, halogen-substituted C 1 -C 6 -alkoxy or halogen-substituted C 1 -C 6 -alkyl;
B 2 represents CR 6 , where R 6 represents hydrogen or C 1 -C 6 -alkyl;
B 4 represents CR 8 , where R 8 represents hydrogen or C 1 -C 6 -alkyl;
B 5 represents CR 9 , where R 9 represents halogen, C 1 -C 6 -alkoxy or C 1 -C 6 -alkyl.
7. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 6 in which
B 1 represents CR 5 , and R 5 represents Cl, Br, I, C 1 -C 6 -alkyl, F-substituted C 1 -C 4 -alkyl or F-substituted C 1 -C 4 -alkoxy,
B 2 represents CR 6 , where R 6 represents hydrogen,
B 4 represents CR 8 , where R 8 represents hydrogen,
B 5 represents CR 9 , where R 9 represents halogen or C 1 -C 4 -alkyl.
8. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
A 1 represents CR 2 , where R 2 represents hydrogen or C 1 -C 4 -alkyl;
A 2 represents nitrogen;
A 3 represents CR 3 , where R 3 represents halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy; and
A 4 represents CR 4 , where R 4 represents hydrogen or C 1 -C 4 -alkyl.
9. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 8 in which
A 1 represents CR 2 , where R 2 represents hydrogen;
A 2 represents nitrogen;
A 3 represents CR 3 , where R 3 represents halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy; and
A 4 represents CR 4 , where R 4 represents hydrogen.
10. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
W represents oxygen,
R 10 represents hydrogen and R 1 represents hydrogen or methyl,
A 1 represents CR 2 , where R 2 represents hydrogen or C 1 -C 4 -alkyl,
A 2 represents nitrogen,
A 3 represents CR 3 , where R 3 represents halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
A 4 represents CR 4 , where R 4 represents hydrogen or C 1 -C 4 -alkyl,
B 1 represents CR 5 , and R 5 represents Cl, Br, I, C 1 -C 4 -alkyl, F-substituted C 1 -C 4 -alkyl or F-substituted C 1 -C 4 -alkoxy,
B 2 represents CR 6 , where R 6 represents hydrogen or C 1 -C 6 -alkyl,
B 3 represents CR 7 , where R 7 represents perhalogenated C 1 -C 4 -alkyl or phenyl,
B 4 represents CR 8 , where R 8 represents hydrogen or C 1 -C 6 -alkyl,
B 5 represents CR 9 , where R 9 represents halogen, C 1 -C 6 -alkoxy or C 1 -C 6 -alkyl,
Q represents cyclopropyl or 1-cyanocyclopropyl.
11. Compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
W represents oxygen,
R 10 represents hydrogen and R 1 represents hydrogen or methyl,
A 1 represents CR 2 , where R 2 represents hydrogen,
A 2 represents nitrogen,
A 3 represents CR 3 , where R 3 represents perfluorinated C 1 -C 4 -alkyl, C 1 -C 4 -alkyl, Cl, F, I or C 1 -C 4 -alkoxy,
A 4 represents CR 4 , where R 4 represents hydrogen,
B 1 represents CR 5 , where R 5 represents F, Cl, Br, C 1 -C 4 -alkyl, F-substituted C 1 -C 4 -alkyl or F-substituted C 1 -C 4 -alkoxy,
B 2 represents CR 6 , where R 6 represents hydrogen,
B 3 represents CR 7 , where R 7 represents perfluorinated C 1 -C 4 -alkyl or phenyl,
B 4 represents CR 8 , where R 8 represents hydrogen,
B 5 represents CR 9 , where R 9 represents F, Cl, Br, I, C 1 -C 4 -alkyl,
Q represents cyclopropyl, 1-cyanocyclopropyl, C 1 -C 4 -alkyl or fluorinated C 1 -C 4 -alkyl.
12. Pharmaceutical composition comprising at least one compound and/or a salt, N-oxide and/or a tautomeric form according to claim 1 and at least one carrier.
13. 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;
A 1 represents CH;
A 2 represents nitrogen,
A 3 represents C—Cl;
A 4 represents CH;
B 1 represents C—Cl;
B 2 represents CH;
B 3 represents C-i-C 3 F 7;
B 4 represents CH;
B 5 represents C—CI;
R 10 represents hydrogen;
W represents oxygen; and
Q represents 1-(cyano)cyclopropyl.
14. The compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 1 in which
R 7 represents halogen, cyano, nitro, C 1 -C 6 -haloalkyl or phenyl.
15. The compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 2 in which
R 1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl.
16. The compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 6 in which
B 1 represents CR 5 , and R 5 represents halogen, C 1 -C 6 -alkoxy or C 1 -C 6 -alkyl, F-substituted C 1 -C 6 -alkoxy or F-substituted C 1 -C 6 -alkyl.
17. The compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 11 in which
A 3 represents CR 3 , where R 3 represents C 1 -C 4 -alkyl , Cl or C 1 -C 4 -alkoxy,
B 1 represents CR 5 , where R 5 represents —CF 3 , —C 2 F 5 , —C 3 F 7 , —C 4 F 9 , —CH 3 , —C 2 H 5 , —C 3 H 7 , —C 4 H 9 , Cl, OCF 3 , OCF 2 H or OCFH 2 ,
B 3 represents CR 7 , where R 7 represents —C 3 F 7 or phenyl,
B 4 represents CR 8 , where R 8 represents hydrogen,
B 5 represents CR 9 , where R 9 represents Cl, Br, I or C 1 -C 4 -alkyl,
Q represents methyl, ethyl, propyl, C 2 H 2 F 3, cyclopropyl or 1-cyanocyclopropyl.
18. The compound of formula (I) and/or a salt, N-oxide and/or a tautomeric form according to claim 11 in which
A 3 represents CR 3 , where R 3 represents methyl, methoxy or Cl,
B 1 represents CR 5 , where R 5 represents Cl, CF 3 , OCF 2 H, OCF 3 , methyl or ethyl,
B 3 represents CR 7 , where R 7 represents —C 3 F 7 or phenyl,
B 4 represents CR 8 , where R 8 represents hydrogen,
B 5 represents CR 9 , where R 9 represents Cl, I, Br, methyl or ethyl,
Q represents methyl, ethyl, propyl, C 2 H 2 F 3 , cyclopropyl or 1-cyanocyclopropyl.