Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-01-20
2000-04-25
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483741, A01N 4356, C07D23116
Patent
active
060544732
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to novel 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides, to a process for their preparation and to their use as microbicides.
BACKGROUND OF THE INVENTION
It is already known that numerous pyrazol carboxamides have fungicidal properties (cf. WO 93-11 117 and EP-A 0 589 313). Thus, for example, N-(2-cycloheptyl)-1,3-dimethyl-5-fluoro-pyrazol-4-carboxanilide and N-(2-sec-butyl-cyclohexyl)-1,3-dimethylpyrazol-4-carboxamide can be employed for controlling fungi. The activity of these compounds is good, but leaves in some cases something to be desired at low application rates.
DETAILED DESCRIPTION OF THE INVENTION
This invention, accordingly, provides novel 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides of the formula ##STR2## in which Represents a grouping of the formula ##STR3## in which R.sup.1 represents alkyl, cycloalkyl, bicycloalkyl, optionally substituted aryl or optionally substituted aralkyl, or 4 carbon atoms, aryl or optionally substituted aralkyl and or 4 carbon atoms.
Furthermore, it has been found that 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides of the formula (I) are obtained when 1,3-dimethyl-5-fluoro-pyrazol-4-carbonyl halides of the formula ##STR4## in which Hal represents fluorine, chlorine or bromine, presence of a diluent.
Finally, it has been found that the novel 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides 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 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides of the formula (I) according to the invention have considerably better fungicidal activity than N-(2-cycloheptyl)-1,3-dimethyl-5-fluoro-pyrazol-4-carboxanilide and N-(2-sec-butylcyclohexyl)-1,3-dimethyl-pyrazol-4-carboxamide, which are constitutionally similar prior-art active compounds of the same direction of action.
The formula (I) provides a general definition of the 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides according to the invention.
R preferably represents a grouping of the formula ##STR5## R.sup.1 preferably represents a straight-chain or branched alkyl having 1 to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, bicycloalkyl having 7 to 12 carbon atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, or 4 carbon atoms, to 12 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, bicycloalkyl having 7 to 12 carbon atoms, phenyl which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety which is optionally mono- to trisubstituted by identical or different substituents selected from the group consisting of halogen and alkyl having 1 to 4 carbon atoms and or 4 carbon atoms.
Particular preference is given to 1,3-dimethyl-5-fluoro-pyrazol-4-carboxamides of the formula (I), in which ##STR6## R.sup.1 represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethyl-butyl, octyl, decyl, dodecyl, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2,2,1]heptyl, phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyl or represents phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, where the phenyl moiety may be mono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl and/or tert-butyl, or different radicals if m represents 2 or 3, or or 4 carbon atoms, isobutyl, tert-butyl, 2-
REFERENCES:
patent: 4134987 (1979-01-01), Huppatz
patent: 4214090 (1980-07-01), Huppatz
patent: 5223526 (1993-06-01), McLoughlin et al.
patent: 5416103 (1995-05-01), Eicken et al.
Chemical Abstracts, vol. 113, No. 1, Jul. 2, 1990, Abst. No. 73387c & JP 1990 85257.
Chemical Abstracts, vol. 109, No. 12/19/88, Abstract No. 231009v and JP 63,048,269 Feb. 29, 1988.
Bielefeldt Dietmar
Dutzmann Stefan
Elbe Hans-Ludwig
Kugler Martin
Stenzel Klaus
Bayer Aktiengesellschaft
Gil Joseph C.
Marmo Carol
Ramsuer Robert W.
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