Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-03-01
2002-04-09
Ramsuer, Robert W. (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C548S374100
Reexamination Certificate
active
06369093
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to novel pyrazole-carboxanilides, to a process for their preparation and to their use for controlling undesirable microorganisms.
BACKGROUND OF THE INVENTION
It is already known that numerous carboxanilides have fungicidal properties (compare WO 93/11 117, EP-A 0 545 099 and EP-A 0 589 301). Thus, N-(2-cyclohexyl)-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide, N-(2-phenyl)-1,3-dimethyl-pyrazole-4-carboxanilide and N-[2-(2-fluoro-phenyl)]-1,3-dimethyl-pyrazole-4-carboxanilide can be used for controlling fungi. The activity of these substances is good, however, it is sometimes unsatisfactory at low application rates.
SUMMARY OF THE INVENTION
Pyrazole-carboxanilides of the formula
wherein m, n, X and Y are as described may be used for controlling undesirable microorganisms.
DETAILED DESCRIPTION
This invention, accordingly, provides novel pyrazole-carboxanilides of the formula
in which
a) m represents the number 0,
n represents the number 1 and
Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-trifluoromethyl,
represents nitro, cyano, hydroxyl, carboxyl, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
or
b) m represents the number 0,
n represents the number 2 or 3 and
Y represents halogen, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
or
c) m represents the number 1,
X represents chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety,
n represents integers from 0 to 3 and
Y represents halogen, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 8 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 8 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkylthio having 1 to 8 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 5 halogen atoms, alkenyloxy having 2 to 8 carbon atoms, alkinyloxy having 2 to 8 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, carbalkoxy having 1 to 8 carbon atoms in the alkoxy moiety or alkoximinoalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 1 to 6 carbon atoms in the alkyl moiety.
Furthermore, it has been found that pyrazole-carboxanilides of the formula (I) are obtained by reacting acyl halides of the formula
in which
Hal represents halogen with aniline derivatives of the formula
in which
X, Y, m and n are each as defined above,
if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent.
Finally, it has been found that the novel pyrazole-carboxanilides of the formula (I) have very good microbicidal properties and can be used for controlling undesirable microorganisms, both in crop protection and in the protection of materials.
Surprisingly, the pyrazole-carboxanilides of the formula (I) according to the invention have considerably better fungicidal activity than N-(2-cyclohexyl)-1,3-dimethyl-5-fluoropyrazole-4-carboxanilide, N-(2-phenyl)-1,3-dimethyl-pyrazole-4-carboxanilide and N-[2-(2-fluoro-phenyl)]-1,3-dimethyl-pyrazole-4-carboxanilide, which are the constitutionally most similar active compounds of the prior art of the same direction of action.
The formula (I) provides a general definition of the pyrazole-carboxanilides according to the invention.
Preference is given to compounds of the formula (I) in which
a) m represents the number 0,
n represents the number 1 and
Y represents 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-trifluoromethyl,
represents nitro, cyano, hydroxyl, carboxyl, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety,
or
b) m represents the number 0,
n represents the number 2 or 3 and
Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety,
or
c) m represents the number 1,
X represents chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine, and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety,
n represents integers from 0 to 3 and
Y represents fluorine, chlorine, bromine, nitro, cyano, hydroxyl, carboxyl, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkenyloxy having 2 to 6 carbon atoms, alkinyloxy having 2 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, carbalkoxy having 1 to 4 carbon atoms in the alkoxy moiety or represents alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety.
Particular preference is given to compounds of the formula (I) in which
a) m rep
Elbe Hans-Ludwig
Jaetsch Thomas
Kuck Karl-Heinz
Kugler Martin
Mauler-Machnik Astrid
Bayer Aktiengesellschaft
Gil Joseph C.
Ramsuer Robert W.
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