Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-03-14
1998-07-28
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514184, 548110, 5482678, 5482686, A01N 43653, C07D24908
Patent
active
057863750
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new hydroxyethyl-azolyl derivatives, a process for their preparation, and to their use as microbicides in plant protection and in the protection of materials.
It has already been disclosed that a large number of hydroxyethyl-azolyl derivatives have fungicidal properties (cf. EP-OS (European Published Specification) 0 251 086, WO 89-05581 and WO 91-12000). 2-(2-Chlorophenyl)-3-(2,4-dichlorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl) -but-1-ene and 2-(2-fluorophenyl)-3-(4-chlorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)-but -1-ene, for example, can be used for combating fungi. In some cases, however, the activity of these substances leaves something to be desired when low application rates are used.
New hydroxyethyl-azolyl derivatives of the formula ##STR2## in which x represents hydrogen, halogen, alkyl having 1 to 4 carbon atoms or alkoxy having 1 to 4 carbon atoms, having 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms, nitro, or phenyl which is optionally monosubstituted to trisubstituted by identical or different halogen atoms, and metal salt complexes have now been found.
The substances according to the invention contain an asymmetrically substituted carbon atom. They can therefore be obtained in the forms of optical isomers. The present invention relates to the individual isomers and also to their mixtures.
Furthermore, it has been found that hydroxyethyl-azolyl derivatives of the formula (I) and their acid addition salts and metal salt complexes are obtained when ##STR3## in which X, Z and m have the abovementioned meanings and ##STR4## in which X, Z and m have the abovementioned meanings, ##STR5## in the presence of an acid-binding agent and in the presence of a diluent and, if appropriate, the resulting compounds of the formula (I) are subsequently subjected to an addition reaction with an acid or a metal salt.
Finally, it has been found that the new hydroxyethyl-azolyl derivatives of the formula (I) and their acid addition salts and metal salt complexes have very good microbicidal properties and can be employed both in plant protection and in the protection of materials.
Surprisingly, the substances according to the invention have better microbicidal activity both in plant protection and in the protection of materials than the previously known compounds of the same direction of action and the most similar constitution. Thus, the substances according to the invention have superior fungidical properties compared with, for example, 2-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-3-hydroxy-4-(1,2, 4-triazol-1-yl)-but-1-ene and 2-(2-fluorophenyl)-3-(4-chlorophenyl) -3-hydroxy-4-(1,2,4-triazol-1-yl) -but-1-ene.
Formula (I) provides a general definition of the hydroxyethyl-azolyl derivatives according to the invention. n-propyl, isopropyl, methoxy and ethoxy. n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, difluoromethoxy, nitro, or represents phenyl which is optionally monosubstituted or disubstituted by identical or different substituents from the series comprising fluorine and/or chlorine. can represent identical or different radicals.
Other preferred substances according to the invention are addition products of acids and those hyroxyethyl-azolyl derivatives of the formula (I) in which X, Z and m have the meanings given as being preferred.
The acids which can be subjected to the addition reaction preferably include hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulphuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as, for example, acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, and also sulphonic acids, such as, for example, p-toluenesulphonic acid, 1,5-naphthal
REFERENCES:
patent: 4911746 (1990-03-01), Holmwood et al.
patent: 4913727 (1990-04-01), Stroech et al.
patent: 4927839 (1990-05-01), Parry et al.
patent: 4980367 (1990-12-01), Cuomo et al.
patent: 4983208 (1991-01-01), Stroech et al
Cram and Hammond, "Organic Chemistry", McGraw-Hill Book Co NY (1964) 2nd Ed. pp. 546-567.
Dehne Heinz-Wilhelm
Dutzmann Stefan
Hanssler Gerd
Lindemann Michael
Bayer Aktiengesellschaft
Morris Patricia L.
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