Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-05-26
2000-01-11
Owens, Amelia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142315, 544146, 549 70, 549 71, 549 72, 549 73, A61K 3138, A61K 31535
Patent
active
060136642
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION
The present invention relates to microbicidal compositions based on thiophene-2-carboxylic acid derivatives, some of which are known, and to the use of these substances for controlling undesired microorganisms. The invention furthermore also relates to new thiophene-2-carboxylic acid derivatives and to a process for their preparation.
BACKGROUND OF THE INVENTION
It has already been disclosed that certain halogen-thiophene carboxylic acid derivatives can be employed for controlling plant diseases (cf. EP-A 0 450 355 and WO 95-27 397). However, the activity of these prior-art compounds is not always satisfactory at low application rates.
Furthermore, a number of 5-trifluoromethyl-4-phenyl-thiophene-2-carboxylic esters are already known (cf. Maybridge Chemical Company, Structure List 1996). However, a microbicidal activity of these substances has not been mentioned to date.
DETAILED DESCRIPTION OF THE INVENTION
It has now been found that the thiophene-2-carboxylic acid derivatives, some of which are known, of the formula ##STR2## in which R.sup.1 represents halogen, cyano, nitro, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, phenyl or phenoxy, ##STR3## where X represents oxygen or sulphur, pyran-4-yl, thiopyran-4-yl, optionally substituted cycloalkyl, optionally substituted cycloalkylalkyl, optionally substituted phenyl or optionally substituted phenylalkyl, and, halogenoalkyl, alkoxyalkyl, alkenyl, alkinyl, alkoxycarbonylalkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted phenyl, optionally substituted phenylalkyl or optionally substituted heterocyclyl or carbon atoms or together represent a radical of the formula --(CH.sub.2).sub.2 --Y--(CH.sub.2).sub.2 -- where
Surprisingly, the thiophene-2-carboxylic acid derivatives of the formula (I) which can be used in accordance with the invention have a considerably better fungicidal activity than the prior-art thiophene-carboxylic acid derivatives of the same indication which have the most similar constitution.
Formula (I) provides a general definition of the thiophene-2-carboxylic derivatives which can be used in accordance with the invention. Preferred thiophene-2-carboxylic acid derivatives of the formula (I) are those in which straight-chain or branched alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, straight-chain or branched alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, phenyl or phenoxy, ##STR4## where X represents oxygen or sulphur, R.sup.3 represents hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms, alkoxyalkyl having 1 to 6 carbon atoms in the alkoxy moiety and 2 to 4 carbon atoms in the alkyl moiety, pyran-4-yl, thiopyran-4-yl, or cycloalkyl having 3 to 7 carbon atoms which can be monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen and/or alkyl having 1 to 4 carbon atoms, or cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety, it being possible for the cycloalkyl moiety to be monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen and/or alkyl having 1 to 4 carbon atoms, or identical or different substituents from the series consisting of halogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, straight-chain or branched alkoxy having 1 to 6 carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 halogen atoms and/or by halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms, or moiety, it being poss
REFERENCES:
patent: 5484807 (1996-01-01), Barnes et al.
Arnaud, R et al Reactivity of Trifluoromethyl Erones in Michael Additions CA 123:168968, 1995.
Dutzmann Stefan
Fischer Reiner
Hanssler Gerd
Lui Norbert
Bayer Aktiengesellschaft
Gil Joseph C.
Marmo Carol
Owens Amelia
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