Biphenyl carboxamides
View Patent ↗The invention relates to novel biphenylcarboxamides of the formula (I) in which R 1 , R 2 , m, n, R 3 , Y and A are as defined in the disclosure, to a plurality of processes for preparing these substances and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.
1. A biphenylcarboxamide of the formula (I)
in which
R 1 and R 2 independently of one another represent hydrogen, halogen, cyano, nitro, C 1 –C 8 -alkyl, C 1 –C 8 -alkoxy, or C 1 –C 8 -alkylthio, or represent C 1 –C 6 -haloalkyl, C 1 –C 6 -haloalkoxy, or C 1 –C 6 -haloalkylthio having in each case 1 to 13 fluorine, chlorine and/or bromine atoms,
m represents 1, 2, 3 or 4, with the proviso that R 1 represents identical or different radicals if m represents 2, 3 or 4,
n represents 1, 2 or 3, with the proviso that R 2 represents identical or different radicals if n represents 2 or 3,
R 3 represents hydrogen, hydroxyl, C 1 –C 6 -alkyl, C 3 –C 6 -cycloalkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkoxy-C 1 –C 6 -alkyl, cyano-C 1 –C 6 -alkyl, C 1 –C 6 -haloalkyl having 1 to 7 halogen atoms, C 1 –C 6 -alkylamino, C 1 –C 6 -alkylsulphenyl, C 1 –C 6 -haloalkyl-sulphenyl having 1 to 7 halogen atoms, (C 1 –C 6 -alkyl)carbonyl, carbamoyl,
Y represents carbonyl or represents C 1 –C 3 -alkylene which is optionally mono- or polysubstituted by identical or different substituents from the group consisting of halogen, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkylthio, C 1 –C 6 -haloalkyl having 1 to 13 flourine, chlorine, and/or bromine atoms, C 1 –C 6 -haloalkoxy having 1 to 13 flourine, chlorine, and/or bromine atoms, and C 1 –C 6 -haloalkylthio having 1 to 13 flourine, chlorine, and/or bromine atoms, and
A represents
(1) a radical of the formula
R 4 represents hydrogen, cyano, halogen, nitro, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylthio, C 1 –C 4 -haloalkylthio having 1 to 5 halogen atoms, aminocarbonyl or aminocarbonyl-C 1 –C 4 -alkyl,
R 5 represents hydrogen, halogen, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, or C 1 –C 4 -alkylthio, and
R 6 represents hydrogen, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, hydroxy-C 1 –C 4 -alkyl, C 2 –C 6 -alkenyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkylthio-C 1 –C 4 -alkyl, C 1 –C 4 -haloalkylthio-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, C 1 –C 4 -haloalkoxy-C 1 –C 4 -alkyl having 1 to 5 halogen atoms or phenyl,
or
(2) a radical of the formula
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents halogen, cyano or C 1 –C 4 -alkyl or C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(3) a radical of the formula
R 10 and R 11 independently of one another represent hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 12 represents hydrogen, C 1 –C 4 -alkyl or halogen,
or
(4) a radical of the formula
R 13 represents hydrogen, halogen, hydroxyl, cyano, C 1 –C 6 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, or C 1 –C 4 -haloalkylthio having 1 to 5 halogen atoms,
or
(5) a radical of the formula
R 14 represents halogen, hydroxyl, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -haloalkylthio having 1 to 5 halogen atoms, or C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, and
R 15 represents hydrogen, halogen, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylsulphinyl, or C 1 –C 4 -alkylsulphonyl,
or
(6) a radical of the formula
R 16 represents C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
R 17 represents C 1 –C 4 -alkyl,
X 1 represents a sulphur atom, represents SO, SO 2 , or CH 2 , and
p represents 0, 1 or 2, with the proviso that R 17 represents identical or different radicals if p represents 2,
or
(7) a radical of the formula
R 18 represents C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(8) a radical of the formula
R 19 represents C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(9) a radical of the formula
R 20 represents halogen, cyano, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
R 21 represents hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 22 represents hydrogen, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, hydroxy-C 1 –C 4 -alkyl, C 1 –C 4 -alkylsulphonyl, di(C 1 –C 4 -alkyl)-aminosulphonyl, C 1 –C 6 -alkylcarbonyl or optionally substituted phenylsulphonyl or benzoyl,
or
(10) a radical of the formula
R 23 and R 24 independently of one another represent hydrogen, halogen, amino, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 25 represents hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(11) a radical of the formula
R 26 and R 27 independently of one another represent hydrogen, halogen, amino, nitro, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 28 represents hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(12) a radical of the formula
R 29 represents hydrogen, halogen, amino, C 1 –C 4 -alkylamino, di-(C 1 –C 4 -alkyl)amino, cyano, C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 30 represents halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(13) a radical of the formula
R 31 represents hydrogen, halogen, amino, C 1 –C 4 -alkylamino, di-(C 1 –C 4 -alkyl)amino, cyano, C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 32 represents halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(14) a radical of the formula
R 33 represents halogen, C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(15) a radical of the formula
R 34 represents hydrogen or C 1 –C 4 -alkyl, and
R 35 represents halogen or C 1 –C 4 -alkyl,
or
(16) a radical of the formula
R 36 represents C 1 –C 4 -alkyl or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms,
or
(17) a radical of the formula
R 37 represents hydrogen, halogen or C 1 –C 4 -alkyl.
2. A biphenylcarboxamide of the formula (I) according to claim 1 in which
R 1 and R 2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1 –C 6 -alkyl, C 1 –C 6 -alkoxy, C 1 –C 6 -alkylthio, or represent C 1 –C 4 -haloalkyl, C 1 –C 4 -haloalkoxy, or C 1 –C 4 -haloalkylthio having in each case 1 to 9 fluorine, chlorine and/or bromine atoms,
m represents 1, 2 or 3, with the proviso that R 1 represents identical or different radicals if m represents 2 or 3,
n represents 1, 2 or 3, with the proviso that R 2 represents identical or different radicals if n represents 2 or 3,
R 3 represents hydrogen, hydroxyl, C 1 –C 4 -alkyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 3 -alkoxy-C 1 –C 2 -alkyl, cyano-C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -aminoalkyl, C 1 –C 4 -alkylsulphenyl, C 1 –C 4 -haloalkyl-sulphenyl having 1 to 5 halogen atoms, or (C 1 –C 4 -alkyl)carbonyl,
Y represents carbonyl or represents C 1 –C 2 -alkylene that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -alkylthio, C 1 –C 4 -haloalkyl having 1 to 9 flourine, chlorine, and/or bromine atoms, C 1 –C 4 -haloalkoxy having 1 to 9 flourine, chlorine, and/or bromine atoms, and C 1 –C 4 -haloalkylthio having 1 to 9 fluorine, chlorine, and/or bromine atoms, and
A represents
(1) a radical of the formula
R 4 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C 1 –C 2 -haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl, or aminocarbonylethyl,
R 5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio, and
R 6 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl or phenyl,
or
(2) a radical of the formula
R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 9 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, or C 1 –C 2 -haloalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(3) a radical of the formula
R 10 and R 11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 12 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl,
or
(4) a radical of the formula
R 13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 –C 4 -alkyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, C 1 –C 2 -haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, or C 1 –C 2 -haloalkylthio having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(5) a radical of the formula
R 14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, C 1 –C 4 -alkyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, or C 1 –C 2 -haloalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, and
R 15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, C 1 –C 4 -alkyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, methoxy, ethoxy, methylthio, ethylthio, C 1 –C 2 -haloalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms, C 1 –C 2 -alkylsulphinyl, or C 1 –C 2 -alkylsulphonyl,
or
(6) a radical of the formula
R 16 represents methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
R 17 represents methyl or ethyl,
X 1 represents a sulphur atom, represents SO, SO 2 , or CH 2 , and
p represents 0, 1 or 2, with the proviso that R 17 represents identical or different radicals if p represents 2,
or
(7) a radical of the formula
R 18 represents methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
(8) a radical of the formula
R 19 represents methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(9) a radical of the formula
R 20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
R 21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 22 represents hydrogen, methyl, ethyl, C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, C 1 –C 2 -alkoxy-C 1 –C 2 -alkyl, hydroxymethyl, hydroxyethyl, methylsulphonyl, or dimethylaminosulphonyl,
or
(10) a radical of the formula
R 23 and R 24 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(11) a radical of the formula
R 26 and R 27 independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms,
or
(12) a radical of the formula
R 29 represents hydrogen, fluorine, chlorine, bromine, amino, C 1 –C 4 -alkylamino, di(C 1 –C 4 -alkyl)amino, cyano, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms and
R 30 represents fluorine, chlorine, bromine, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
(13) a radical of the formula
R 31 represents hydrogen, fluorine, chlorine, bromine, amino, C 1 –C 4 -alkylamino, di(C 1 –C 4 -alkyl)amino, cyano, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, and
R 32 represents fluorine, chlorine, bromine, methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
(14) a radical of the formula
R 33 represents fluorine, chlorine, bromine, methyl, ethyl or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
(15) a radical of the formula
R 34 represents hydrogen, methyl, or ethyl, and
R 35 represents fluorine, chlorine, bromine, methyl, or ethyl,
or
(16) a radical of the formula
R 36 represents methyl, ethyl, or C 1 –C 2 -haloalkyl having 1 to 5 fluorine, chlorine and/or bromine atoms,
or
(17) a radical of the formula
R 37 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl.
3. A biphenylcarboxamide of the formula (I) according to claim 1 in which
R 1 and R 2 independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, difluorochloromethylthio,
m represents 1 or 2, with the proviso that R 1 represents identical or different radicals if m represents 2,
n represents 1 or 2, with the proviso that R 2 represents identical or different radicals if n represents 2,
R 3 represents hydrogen, hydroxyl, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxy, ethoxy, methoxymethyl, cyanomethyl, difluoromethyl, methylsulphenyl, trichloromethylsulphenyl or acetyl,
Y represents carbonyl or represents —CH 2 — or —(CH 2 ) 2 — that are each optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy, and trifluoromethylthio, and
A represents
(1) a radical of the formula
R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio
R 5 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio, and
R 6 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl,
or
(2) a radical of the formula
R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 9 represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, or trichloromethoxy,
or
(3) a radical of the formula
R 10 and R 11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 12 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl,
or
(4) a radical of the formula
R 13 represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio, or trichloromethylthio,
or
(5) a radical of the formula
R 14 represents fluorine, chlorine, bromine, iodine, hydroxyl, cyano, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, or trichloromethoxy, and
R 15 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulphinyl, or methylsulphonyl,
or
(6) a radical of the formula
R 16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
R 17 represents methyl or ethyl,
X 1 represents a sulphur atom or represents SO, SO 2 , or CH 2 , and
p represents 0, 1 or 2, with the proviso that R 17 represents identical or different radicals if p represents 2,
or
(7) a radical of the formula
R 18 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(8) a radical of the formula
R 19 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(9) a radical of the formula
R 20 represents fluorine, chlorine, bromine, cyano, methyl, ethyl, i-propyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
R 21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 22 represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl, or hydroxyethyl,
or
(10) a radical of the formula
R 23 and R 24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(11) a radical of the formula
R 26 and R 27 independently of one another represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 28 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(12) a radical of the formula
R 29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 30 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(13) a radical of the formula
R 31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl, and
R 32 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(14) a radical of the formula
R 33 represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(15) a radical of the formula
R 34 represents hydrogen, methyl, or ethyl, and
R 35 represents fluorine, chlorine, bromine, methyl, or ethyl,
or
(16) a radical of the formula
R 36 represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, or trichloromethyl,
or
(17) a radical of the formula
R 37 represents hydrogen, fluorine, chlorine, bromine, methyl, or ethyl.
4. A biphenylcarboxamide of the formula (I) according to claim 1 in which
R 1 and R 2 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, methoxy, ethoxy, methylthio, ethylthio, trichloromethyl, trifluoromethyl, difluoromethyl, trifluoromethoxy, trifluoromethylthio,
m represents 1 or 2, with the proviso that R 1 represents identical or different radicals if m represents 2,
n represents 1,
R 3 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-, i-, s-, or t-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
Y represents carbonyl or represents —CH 2 — or —(CH 2 ) 2 — that are each optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, methyl, i-propyl, t-butyl, methoxy, i-propoxy, t-butoxy, methylthio, i-propylthio, t-butylthio, trifluoromethyl, trifluoromethoxy, and trifluoromethylthio, and
A represents
(1) a radical of the formula
R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, i-propyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, or trichloromethyl,
R 5 represents hydrogen, fluorine, chlorine, bromine, iodine, or methyl, and
R 6 represents hydrogen, methyl, trifluoromethyl, or phenyl,
or
(2) a radical of the formula
R 7 and R 8 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, or trichloromethyl, and
R 9 represents fluorine, chlorine, bromine, methyl or trifluoromethoxy,
or
(3) a radical of the formula
R 10 and R 11 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, or trichloromethyl, and
R 12 represents hydrogen, fluorine, chlorine, bromine or methyl,
or
(4) a radical of the formula
R 13 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl, or trichloromethyl,
or
(5) a radical of the formula
R 14 represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 15 represents hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, methylsulphinyl, or methylsulphonyl,
or
(6) a radical of the formula
R 16 represents methyl, ethyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
R 17 represents methyl or ethyl,
X 1 represents a sulphur atom or represents SO, SO 2 , or CH 2 , and
p represents 0, 1 or 2, with the proviso that R 17 represents identical or different radicals if p represents 2,
or
(7) a radical of the formula
R 18 represents methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(8) a radical of the formula
R 19 represents methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(9) a radical of the formula
R 20 represents fluorine, chlorine, bromine, methyl, i-propyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
R 21 represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 22 represents hydrogen, methyl, ethyl, trifluoromethyl, or methoxymethyl,
or
(10) a radical of the formula
R 23 and R 24 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 25 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(11) a radical of the formula
R 26 and R 27 independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 28 represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(12) a radical of the formula
R 29 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 30 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(13) a radical of the formula
R 31 represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl, and
R 32 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(14) a radical of the formula
R 33 represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(15) a radical of the formula
R 34 represents hydrogen, methyl, or ethyl, and
R 35 represents fluorine, chlorine, bromine, methyl, or ethyl,
or
(16) a radical of the formula
R 36 represents methyl, trifluoromethyl, difluoromethyl, or trichloromethyl,
or
(17) a radical of the formula
R 37 represents hydrogen, fluorine, chlorine, bromine, or methyl.
5. A biphenylcarboxamide of the formula (I) according to claim 1 in which
R 1 represents hydrogen, fluorine, chlorine, methyl,
R 2 represents hydrogen,
m represents 1 or 2, with the proviso that R 1 represents identical or different radicals if m represents 2,
n represents 1,
R 3 represents hydrogen,
Y represents —CH 2 —, —(CH 2 ) 2 —, —CF 2 —, or —(CF 2 ) 2 —, and
A represents
(1) a radical of the formula
R 4 represents methyl, monofluoromethyl, difluoromethyl, or trifluoromethyl, and
R 5 represents hydrogen, fluorine, chlorine, or methyl, and
R 6 represents methyl,
or
(2) a radical of the formula
R 7 and R 8 represent hydrogen, and
R 9 represents methyl,
or
(3) a radical of the formula
R 10 and R 11 represent hydrogen, and
R 12 represents methyl,
or
(4) a radical of the formula
R 13 represents iodine, methyl, difluoromethyl, or trifluoromethyl,
or
(5) a radical of the formula
R 20 represents methyl, trifluoromethyl, or difluoromethyl,
R 21 represents hydrogen, fluorine, chlorine, methyl, trifluoromethyl, or difluoromethyl, and
R 22 represents hydrogen, methyl, ethyl, trifluoromethyl, or methoxymethyl,
or
(6) a radical of the formula
R 23 and R 24 represent hydrogen, and
R 25 represents methyl,
or
(7) a radical of the formula
R 26 and R 27 represent hydrogen, and
R 28 represents methyl,
or
(8) a radical of the formula
R 29 represents amino, methylamino, dimethylamino, methyl, or trifluoromethyl, and
R 30 represents methyl, trifluoromethyl, or difluoromethyl,
or
(9) a radical of the formula
R 31 represents amino, methylamino, dimethylamino, methyl, or trifluoromethyl, and
R 32 represents methyl, trifluoromethyl, or difluoromethyl,
or
(10) a radical of the formula
R 36 represents methyl or trifluoromethyl.
6. A process for preparing biphenylcarboxamide of formula (I) according to claim 1 comprising
a) reacting a carboxylic acid derivatives of formula (II)
in which
A is as defined for formula (I) in claim 1 , and
G represents halogen, hydroxyl or C 1 –C 6 -alkoxy, with an aniline derivative of formula (III)
in which R 1 , R 2 , m, n, R 3 and Y are as defined for formula (I) in claim 1 , optionally in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent,
or
b) reacting a carboxamide derivative of formula (IV)
in which R 1 , m, R 3 and A are as defined for formula (I) in claim 1 , with a boronic acid derivative of formula (V)
in which
R 2 , n and Y are as defined for formula (I) in claim 1 , and
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene, in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent,
or
c) reacting a carboxamide boronic acid derivative of formula (VI)
in which
R 1 , m, R 3 and A are as defined for formula (I) in claim 1 , and
G 1 and G 2 each represent hydrogen or together represent tetramethylethylene, with phenyl derivative of formula (VII)
in which R 2 , n and Y are as defined for formula (I) in claim 1 , in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent,
or
d) reacting a carboxamide derivative of formula (IV)
in which R 1 , m, R 3 and A are as defined for formula (I) in claim 1 , with phenyl derivative of formula (VII)
in which R 2 , n and Y are as defined for formula (I) in claim 1 , in the presence of a palladium or platinum catalyst, in the presence of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder, and optionally in the presence of a diluent.
7. A composition for controlling unwanted microorganisms comprising one or more biphenylcarboxamides of formula (I) according to claim 1 and one or more extenders and/or surfactants.
8. A process for preparing compositions for controlling unwanted microorganisms comprising mixing one or more biphenylcarboxamides of formula (I) according to claim 1 with one or more extenders and/or surfactants.
9. A method for controlling unwanted microorganisms comprising applying to the microorganisms and/or their habitats an effective amount of one or more biphenylcarboxamides of formula (I)
in which
R 1 , R 2 , and R 3 represent hydrogen,
m and n represent 1,
Y represents C 1 –C 3 -alkylene that is mono- or polysubstituted by fluorine, and
A represents
(1) a radical of the formula
R 4 represents hydrogen, cyano, halogen, nitro, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylthio, C 1 –C 4 -haloalkylthio having 1 to 5 halogen atoms, aminocarbonyl, or aminocarbonyl-C 1 –C 4 -alkyl,
R 5 represents hydrogen, halogen, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, or C 1 –C 4 -alkylthio, and
R 6 represents hydrogen, C 1 –C 4 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, hydroxy-C 1 –C 4 -alkyl, C 2 –C 6 -alkenyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkylthio-C 1 –C 4 -alkyl, C 1 –C 4 -haloalkylthio-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, C 1 –C 4 -haloalkoxy-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, or phenyl,
or
(2) a radical of the formula
R 7 and R 8 independently of one another represent hydrogen, halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 9 represents halogen, cyano or C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms,
or
(3) a radical of the formula
where R 13 represents hydrogen, halogen, hydroxyl, cyano, C 1 –C 6 -alkyl, C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms, C 1 –C 4 -haloalkoxy having 1 to 5 halogen atoms, or C 1 –C 4 -haloalkylthio having 1 to 5 halogen atoms,
or
(4) a radical of the formula
R 29 represents hydrogen, halogen, amino, C 1 –C 04 -alkylamino, di(C 1 –C 4 -alkyl)amino, cyano, C ′ –C 4 -alkyl, or C ′ –C 4 -haloalkyl having 1 to 5 halogen atoms, and
R 30 represents halogen, C 1 –C 4 -alkyl, or C 1 –C 4 -haloalkyl having 1 to 5 halogen atoms.