Disubstituted pyrazolyl carboxanilides
View Patent ↗This invention relates to novel pyrazolylcarboxanilides of formula (I) in which R, R 1 , R 2 and R 3 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 pyrazolylcarboxanilide of formula (I)
in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulphonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulphonyl having in each case 1 to 5 halogen atoms, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
2. A pyrazolylcarboxanilide of formula (I) according to claim 1 in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or i-propylthio, cyclopropyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
3. A pyrazolylcarboxanilide of formula (I) according to claim 1 in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethoxy, or trifluoromethoxy, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
4. A pyrazolylcarboxanilide of formula (I) according to claim 1 in which R 1 represents fluorine and R 2 represents chlorine.
5. A pyrazolylcarboxanilide of formula (I) according to claim 1 in which R 1 represents fluorine and R 2 represents fluorine.
6. A pyrazolylcarboxanilide of formula (I) according to claim 1 in which R 1 represents methyl or trifluoromethyl and R 2 represents fluorine.
7. A compound of formula (Ia)
in which
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
8. A compound of formula (Ib)
in which
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
9. A compound of formula (Ic)
in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
10. A compound of formula (Id)
in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difiluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
11. A compound of formula (Ie)
in which
R represents difluoromethyl or trifluoromethyl,
R 1 and R 2 independently of one another represent fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, trifluoromethyl, trichloromethyl, trifluoroethyl, cyclopropyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, with the proviso that at least one of R 1 and R 2 is fluorine, and
R 3 represents fluorine.
12. A process for preparing a pyrazolylcarboxanilide of formula (I) according to claim 1 comprising
(a) reacting a pyrazolylcarbonyl halide of formula (II)
in which
R is as defined for formula (I) in claim 1 , and
X 1 represents halogen,
with an aniline derivative of formula (III)
in which R 1 , R 2 , and R 3 are as defined for formula (I) in claim 1 , optionally in the presence of an acid binder and optionally in the presence of a diluent, or
(b) reacting a halopyrazolecarboxanilide of formula (IV)
in which
R and R 3 are as defined for formula (I) in claim 1 , and
X 2 represents bromine or iodine,
with a boronic acid derivative of formula (V)
in which
R 1 and R 2 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 in a first step a halopyrazolecarboxanilide of formula (IV)
in which
R and R 3 are as defined for formula (I) in claim 1 , and
X 2 represents bromine or iodine,
with a diborane derivative of formula (VI)
in which G 3 and G 4 each represent alkyl or together represent alkanediyl,
in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent, and
reacting without work-up in a second step with a halobenzene derivative of the formula (VII)
in which
R 1 and R 2 are as defined for formula (I) in claim 1 , and
X 3 represents bromine, iodine, or trifluoromethylsulphonyloxy,
in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent.
13. A composition for controlling unwanted microorganisms comprising one or more pyrazolylcarboxanilides of formula (I) according to claim 1 and one or more extenders and/or surfactants.
14. A method for controlling unwanted microorganisms comprising applying an effective amount of a pyrazolylcarboxanilide of formula (I) according to claim 1 to the microorganisms and/or their habitat.
15. A process for preparing a composition for controlling unwanted microorganisms comprising mixing a pyrazolylcarboxanilide of formula (I) according to claim 1 with one or more extenders and/or surfactants.