N-substituted pyrazolyl carboxanilides
View Patent ↗The invention relates to novel N-substituted pyrazolylcarboxanilides of the formula (I) in which R 1 , R 2 , R 3 , and R 4 are as defined in the disclosure, to a plurality of processes for preparing these compounds and their use for controlling unwanted microorganisms, and to novel intermediates and their preparation.
1. An N-substituted pyrazolylcarboxanilide of formula (I)
in which
R 1 represents methyl, trifluoromethyl, or difluoromethyl,
R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl,
either
(a) R 3 represents hydrogen, and
R 4 represents C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 alkyl, C 1 -C 6 -haloalkyl, or —C(═O)C(═O)R 5 ,
or
(b) R 3 represents halogen, C 1 -C 8 -alkyl, or C 1 -C 8 -haloalkyl, and
R 4 represents C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, or —C(═O)C(═O)R 5 , and
R 5 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; or represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.
2. An N-substituted pyrazolylcarboxanilide of formula (I) according to claim 1 in which
R 1 represents methyl, trifluoromethyl, or difluoromethyl,
R 2 represents hydrogen, fluorine, chlorine, methyl, or trifluoromethyl,
either
(a) R 3 represents hydrogen, and
R 4 represents C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkyl, or —C(═O)C(═O)R 5 ,
or
(b) R 3 represents fluorine, chlorine, bromine, iodine, C 1 -C 6 -alkyl, or C 1 -C 6 -haloalkyl having 1 to 13 fluorine, chlorine, and/or bromine atoms, and
R 4 represents C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 1 -C 4 -haloalkyl, or —C(═O)C(═O)R 5 , and
R 5 represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.
3. An N-substituted pyrazolylcarboxanilide of formula (Ib)
in which
R 4A represents C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, or —C(═O)C(═O)R 5 ,
R 1 represents methyl, trifluoromethyl, or difluoromethyl,
R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, and
R 5 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; or represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.
4. An N-substituted pyrazolylcarboxanilide of formula (Ic)
in which
R 3B represents halogen, C 1 -C 8 -alkyl, or C 1 -C 8 -haloalkyl,
R 4B represents C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl, or —C(═O)C(═O)R 5 ,
R 1 represents methyl, trifluoromethyl, or difluoromethyl,
R 2 represents hydrogen, fluorine, chlorine, methyl or trifluoromethyl, and
R 5 represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; or represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms.
5. An N-substituted pyrazolylcarboxanilide of formula (I) according to claim 1 in which R 4 represents —C(═O)C(═O)R 5 and R 5 is as defined in claim 1 .
6. A composition for controlling unwanted microorganisms comprising one or more N-substituted pyrazolylcarboxanilides of formula (I) according to claim 1 and one or more extenders and/or surfactants.
7. A method of controlling unwanted microorganisms comprising applying an effective amount of an N-substituted pyrazolylcarboxanilide of formula (I) according to claim 1 to the microorganisms and/or their habitat.