Alkyl-analide producing method
View Patent ↗New pyrazolylcarboxanilides of the formula (I) in which R and R 1 have the meanings given in the description, a plurality of processes for the preparation of these substances and their use for controlling undesired microorganisms, and novel intermediates and their preparation.
1. A compound of formula (I)
wherein
R is difluoromethyl or trifluoromethyl, and
R 1 is chloro or methyl.
2. The compound of formula (I) according to claim 1 , selected from the group consisting of
N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,
N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,
N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-1-methyl-3-(difluoromethyl)-1H-pyrazole-4-carboxamide, and
N-(3′,5-difluoro-4′-methylbiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide.
3. A process for preparation of the compound of formula (I) according to claim 1 , comprising reacting
a) a compound of formula (II)
wherein
R is difluoromethyl or trifluoromethyl, and
X 1 is halo,
with a compound of formula (III)
wherein
R 1 is chloro or methyl,
optionally in the presence of an acid binder and optionally in the presence of a diluent, or
b) a compound of formula (IV)
wherein
R is difluoromethyl or trifluoromethyl, and
X 2 is bromo or iodo
with a compound of formula (V)
wherein
R 1 is chloro or methyl and
G 1 and G 2 are in each case hydrogen or together are tetramethylethylene, in the presence of a catalyst, optionally an acid binder and optionally a diluent, or
c) a compound of formula (IV)
wherein
R is difluoromethyl or trifluoromethyl, and
X 2 is bromo or iodo
in a first step, with a compound of formula (VI)
wherein
G 3 and G 4 are in each case alkyl or together are alkanediyl, in the presence of a catalyst, optionally an acid binder and optionally a diluent and, without work-up, in a second step with a compound of formula (VII)
wherein
R 1 is chloro or methyl and
X 3 is bromo, iodo or trifluoromethylsulphonyloxy
in the presence of a catalyst, optionally an acid binder and optionally a diluent.
4. A composition for controlling undesired microorganisms, comprising the compound of formula (I) according to claim 1 , and an extender, a surface-active substance, or combinations thereof.
5. A method of controlling undesired microorganisms, comprising contacting the compound of formula (I) according to claim 1 with a microorganism or its environment.
6. A process for preparation of a composition for controlling undesired microorganisms, comprising mixing the compound of formula (I) according to claim 1 with an extender or a surface-active substance.
7. An aniline derivative of formula (III)
wherein
R 1 is chloro or methyl.
8. The method of claim 5 , wherein the undesired microorganisms are on crops.
9. The method of claim 5 , wherein the undesired microorganisms are on materials.
10. The compound of formula (I) according to claim 1 , which is N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.
11. The process of claim 3 , wherein the compound of formula (I) is N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.
12. The composition of claim 4 , wherein the compound of formula (I) is N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.
13. The method of claim 5 , wherein the compound of formula (I) is N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.
14. The process of claim 6 , wherein the compound of formula (I) is N-(4′-chloro-3′,5-difluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.