1,3,2-benzodithiazol-1-oxides as microbiocides

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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548123, A01N 4382, A01N 4378, C07D27762, C07D27716

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057671370

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BRIEF SUMMARY
This application is a 371 OF PCT/EP95/00283 Jan. 26, 1995.
The invention relates to the microbicidal use of 1,3,2-benzodithiazole 1-oxides, to novel 1,3,2-benzodithiazole 1-oxides and to processes for their preparation.
It is already known that certain 1,3,2-benzodithiazole 1-oxides have an antimycotic action in pharmaceutical compositions (see U.S. Pat. No. 5,140,018). their use in the protection of materials are known (see e.g. DE-A 4 027 378, GB 1 531 431, EP 18 100). The activity and breadth of action of these compounds, however, is not always completely satisfactory, especially at low concentrations. Surprisingly, the 1,3,2-benzodithiazole 1-oxides according to the invention have not only a greater breadth of action but also a markedly higher activity.
It has been found that the 1,3,2-benzodithiazole 1-oxides--some of which are known--of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen, optionally substituted alkyl, alkoxy, alkenyl, alkinyl, cycloalkyl, aryl, heteroaryl or aralkyl, or heteroarylalkyl, and represent hydrogen, halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, dialkylamino, nitro or cyano
A general definition of the 1,3,2-benzodithiazole 1-oxides which can be used in accordance with the invention is given by the formula (I). Preference is given to compounds of the formula (I) in which 18 carbon atoms, straight-chain or branched alkenyl having 2 to 18 carbon atoms or straight-chain or branched alkinyl having 2 to 18 carbon atoms which is optionally substituted one or more times by identical or different substituents consisting of halogen, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 9 identical or different halogen atoms, acyl having 1 to 6 carbon atoms, acyloxy having 1 to 6 carbon atoms, (alkoxy)-carbonyl having 1 to 6 carbon atoms, amino which is optionally substituted by identical or different substituents consisting of alkyl or aryl, optionally substituted phenoxy or pyridyloxy, nitro or cyano, having 3 to 18 carbon atoms which is optionally substituted one or more times by identical or different substituents consisting of halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, nitro or cyano, by halogen, alkyl having 1 to 10 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, alkoxy having 1 to 10 carbon atoms, halogenoalkoxy having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, alkylthio having 1 to 10 carbon atoms, halogenoalkylthio having 1 to 8 carbon atoms and 1 to 8 identical or different halogen atoms, amino, monoalkylamino having straight-chain or branched alkyl radicals having 1 to 6 carbon atoms, dialkylamino having identical or different; straight-chain or branched alkyl radicals each having 1 to 6 carbon atoms, cycloalkyl having 1 to 6 carbon atoms, methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, nitro or cyano, and consists of 1 to 8 carbon atoms and aryl preferably represents phenyl which is optionally substituted from one to four times by identical or different substituents consisting of halogen, alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1 to 6 carbon atoms and 1 to 6 identical or different halogen atoms, alkoxy having 1 to 6 carbon atoms, halogenoalkoxy having 1 to 6 carbon atoms and 1 to 6 identical or different halogen atoms, alkylthio having 1 to 6 carbon atoms, halogenoalkylthio having 1 to 6 carbon atoms and 1 to 6 identical or different halogen atoms, amino, monoalkylamino having

REFERENCES:
patent: 5131939 (1992-07-01), Hsu
patent: 5140018 (1992-08-01), Klein et al.
Klein et al., Synthesis and Antifungal Activity of 1,3,2-Benzodithiazol.S-Oxides, Journal of Medicinal Chemistry, vol. 37, No. 5, pp. 572-578, Aug. 1993.

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