Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-05-14
1998-08-04
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5482632, 5482644, A01N 43653, C07D24912
Patent
active
057894302
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/04392 filed Nov. 8, 1995.
The present invention relates to new triazolyl derivatives, to a plurality of processes for their preparation, and to their use as microbicides.
It has already been disclosed that a large number of hydroxyethyl-azolyl derivatives have fungicidal properties (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0 061 835 and EP-A 0 297 345). However, the applicability of these substances is not always satisfactory in some cases.
There have now been found new triazolyl derivatives of the formula ##STR2## in which R.sup.1 and R.sup.2 are identical or different and represent optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aralkyl, optionally substituted aralkenyl, optionally substituted aroxyalkyl, optionally substituted aryl or optionally substituted heteroaryl and --R.sup.3 or --SO.sub.3 H, in which chlorine, alkenyl which is optionally substituted by fluorine and/or chlorine, optionally substituted aralkyl or optionally substituted aryl,
Those substances according to the invention in which R.sup.1 and R.sup.2 are different have an asymmetrically substituted carbon atom. They can therefore be obtained in the form of optical isomers. The present invention relates to the individual isomers as well as their mixtures.
Furthermore, it has been found that triazolyl derivatives of the formula (I) and their acid addition salts and metal salt complexes are obtained when ##STR3## in which R.sup.1 and R.sup.2 have the abovementioned meanings, either presence of a diluent and the product is then hydrolysed with water, if appropriate in the presence of an acid, or and then treated, if appropriate, with water and, if appropriate, with acid, and (.beta.), of the formula ##STR4## in which R.sup.1 and R.sup.2 have the abovementioned meanings, are reacted with halogen compounds of the formula chlorine, alkenyl which is optionally substituted by fluorine and/or chlorine or optionally substituted aralkyl and and, if appropriate, the resulting compounds of the formula ##STR5## in which R.sup.1, R.sup.2 and R.sup.4 have the abovementioned meanings, are reacted with oxidants in the presence of a diluent, or ##STR6## in which R.sup.1 and R.sup.2 have the abovementioned meanings, are reacted in succession with strong bases and diaryl disulphides of the formula of the formula ##STR7## in which R.sup.1, R.sup.2 and R.sup.5 have the abovementioned meanings, are reacted with oxidants in the presence of a diluent, or ##STR8## in which R.sup.1 and R.sup.2 have the abovementioned meanings, are reacted with potassium permanganate in the presence of a diluent, subjected to an addition reaction with an acid or a metal salt.
Finally, it has been found that the new triazolyl derivatives of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be used both in plant protection and in materials protection to control undesirable microorganisms, such as fungi.
Surprisingly, the substances according to the invention have a better microbicidal activity, in particular fungicidal activity than those compounds of the same direction of action which are most similar constitutionally.
Formula (I) provides a general definition of triazolyl derivatives according to the invention. 6 carbon atoms, it being possible for these radicals to be monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, alkoxy having 1 to 4 carbon atoms, alkoximino having 1 to 4 carbon atoms in the alkoxy moiety and/or cycloalkyl having 3 to 7 carbon atoms, or it being possible for each of these radicals to be monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, alkoxy having 1 to 4 carbon atoms and/or cycloalkyl having 3 to 7 carbon atoms, or each of these radicals to be monosubstituted to trisubstituted by identical or different substituents from the series consisting of
REFERENCES:
patent: 4952232 (1990-08-01), Cuomo et al.
Cram & Hammond, "Organic Chemistry", McGraw Hill Book Co., NY 2nd Ed pp. 565-567, 1964.
C. Yamazaki, et al., J. Chem. Soc. Perkin Trans. 1, pp. 1567-1572, (1987).
Dutzmann Stefan
Hanssler Gerd
Jautelat Manfred
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Morris Patricia L.
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