Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-11-14
1998-01-27
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549 53, A01N 4312, C07D33370
Patent
active
057123047
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new benzothiophenecarboxamide S-oxides, to a process for their preparation, and to their use as microbicides in plant protection and in the protection of materials.
It has been disclosed that certain benzothiophenecarboxamide S,S-dioxides, such as, for example, the compound N-(methyl)-benzothiophene-2-carboxamide S,S-dioxide, have fungicidal properties (cf., for example, DE-OS (German Published Specification) 4,115,184).
However, the effectiveness of these prior-art compounds is not entirely satisfactory in all fields of application, in particular when low amounts and concentrations are applied.
New benzothiophenecarboxamide S-oxides of the formula (I) ##STR2## have been found in which R.sup.1 represents optionally substituted alkyl, or represents alkenyl or alkinyl, or represents in each case optionally substituted cycloalkyl or cycloalkylalkyl, or represents in each case optionally substituted aralkyl, aralkenyl, aralkinyl or aryl and bonded represent an optionally substituted heterocycle, case represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, and
If appropriate, the compounds of the formula (I) can exist in the form of geometric and/or optical isomers or variously composed mixtures of isomers, depending on the nature of the substituents. The pure isomers and also the isomer mixtures are claimed according to the invention.
Furthermore, it has been found that the new substituted thiophenecarboxamides of the formula (I) ##STR3## in which R.sup.1 represents optionally substituted alkyl, or represents alkenyl or alkinyl, or represents in each case optionally substituted cycloalkyl or cycloalkylalkyl, or represents in each case optionally substituted aralkyl, aralkenyl, aralkinyl or aryl and bonded represent an optionally substituted heterocycle, case represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio, and ##STR4## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 and R.sup.7 have the abovementioned meaning and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel benzothiophenecarboxamide S-oxides of the formula (I) have powerful microbicidal properties and can be employed both in plant protection and in the protection of materials.
Surprisingly, the benzothiophenecarboxamide S-oxides of the formula (I) according to the invention display a considerably better effectiveness against plant-pathogenic microorganisms than, for example, the compound N-(methyl)-benzothiophene-2-carboxamide S,S-dioxide, which is a prior-art active compound having the same direction of action and similar constitution.
Formula (I) provides a general definition of the benzothiophenecarboxamide S-oxides according to the invention. 20 carbon atoms which is optionally substituted by a nitrogen-bonded, saturated heterocycle which has 1 nitrogen atom and 2 to 6 carbon atoms and which can additionally be substituted by halogen, in each case straight-chain or branched alkyl or alkoxy, each of which has 1 to 4 carbon atoms, or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, or represents in each case straight-chain or branched halogenoalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxycarbonylalkyl, each of which has 1 to 8 carbon atoms in the individual alkyl moieties, or represents straight-chain or branched alkenyl having 2 to 12 carbon atoms, or represents straight-chain or branched alkinyl having 2 to 12 carbon atoms, or represents cycloalkylalkyl or cycloakyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally mono- to hexa-substituted in the cycloalkyl moiety by identical or different substituents, suitable cycloalkyl substituents in each case being: atoms or in each case straight-chain or branched halogenoalkyl having 1 to 4 car
REFERENCES:
patent: 3636050 (1972-01-01), Driscoll et al.
patent: 5244893 (1993-09-01), Elbe et al.
patent: 5342835 (1994-08-01), Pepin et al.
patent: 5356926 (1994-10-01), Boschelli et al.
Dehne Heinz-Wilhelm
Elbe Hans-Ludwig
Kugler Martin
Lantzsch Reinhard
Paulus Wilfried
Bayer Aktiengesellschaft
Morris Patricia L.
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