Pyrazolecarboxanilides, process for their preparation and compositions comprising them for controlling harmful fungi
The present invention relates to pyrazolecarboxanilides I in which the variables are as defined below: n is zero or 2; m is 2 or 3; X 1 is fluorine or chlorine; X 2 is halogen; Y is CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, methoxy or methylthio; p is zero or 1; R 1 is fluorine, chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 2 is hydrogen or halogen; R 3 is hydrogen, methyl or ethyl; W is O or S; with the proviso that, if a) W=O, R 1 =methyl and R 3 is hydrogen, R 2 is not fluorine, or b) W=O, n=0, m=2, p=0, R 2 and R 3 are hydrogen, R 1 is not trifluoromethyl or difluoromethyl, to processes for preparing these compounds, to compositions comprising them and to methods for using them for controlling harmful fungi.
1. A pyrazolecarboxanilide of the formula I
in which the variables are as defined below:
n is zero;
m is 3;
X 2 is halogen, where the radicals X 2 may have different meanings;
p is zero;
R 1 is C 1 -C 4 -haloalkyl;
R 2 is hydrogen or halogen;
R 3 is hydrogen; and
W is O.
2. The pyrazolecarboxanilide of the formula I according to claim 1 in which the variables are as defined below:
X 2 is fluorine or chlorine;
R 1 is fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl; and
R 2 is hydrogen, fluorine or chlorine.
3. The pyrazolecarboxanilide of the formula I according to claim 1 in which the variables are as defined below:
X 2 is fluorine or chlorine,
R 1 is fluoromethyl, difluoromethyl, chlorofluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl or trifluoromethyl; and
R 2 is hydrogen or chlorine.
4. The pyrazolecarboxanilide of the formula I according to claim 1 , selected from the group consisting of:
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,
N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,
N-(2′,3′,4′-trifluorobiphenyl-2-yl)-1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,
N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-chlorodifluoromethyl-1H-pyrazole-4-carboxamide,
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-chlorofluoromethyl-1H-pyrazole-4-carboxamide,
N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-fluoromethyl-1H-pyrazole-4-carboxamide,
N-(2′,3′,4′-trifluorobiphenyl-2-yl)-1-methyl-3-fluoromethyl-1H-pyrazole-4-carboxamide, and
N-(2′,4′,5′-trifluorobiphenyl-2-yl)-1-methyl-3-fluoromethyl-1H-pyrazole-4-carboxamide.
5. A composition for controlling harmful fungi, which composition comprises a fungicidal amount of a compound of the formula I according to claim 1 and at least one inert additive.
6. The composition according to claim 5 , additionally comprising a further active compound.
7. A method for controlling phytopathogenic harmful fungi, which comprises treating the harmful fungi, their habitat and/or the materials, plants, the soil or seed to be protected against fungal attack with a fungicidally effective amount of a compound of the formula I according to claim 1 .
8. Seed, comprising a compound of the formula I according to claim 1 in an amount of from 1 to 1000 g/100 kg.
9. An aniline of the formula III
wherein the variables n, m, X 1 and X 2 have the meanings given in claim 1 .