Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-01-20
1999-06-08
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514619, A01N 3718, A01N 4354
Patent
active
059105003
DESCRIPTION:
BRIEF SUMMARY
This Application is a 371 of PCT/EP96/03353 filed on Jul. 30, 1996.
The present invention relates to a fungicidal mixture which comprises ##STR3## where R is hydrogen or halogen and b) a pyrimidine derivative of the formula II ##STR4## where R is methyl, propyn-1-yl or cyclopropyl, in a synergistically active amount.
Moreover, the invention relates to methods of controlling harmful fungi using the compounds I and II, or synergistic mixtures comprising them, and to the use of the compounds I and of the compounds II for the preparation of such mixtures.
Compounds of the formula I, their preparation and their action against harmful fungi is disclosed in the literature (WO-A 95/18,789).
Also disclosed are the pyrimidine derivatives II, their preparation, and pyrimethanil); R=1-propynyl: EP-A 224 339 (common name: mepanipyrim); R=cyclopropyl: EP-A 310 550!. have an improved action against harmful fungi combined with a reduced total amount of active ingredients applied (synergistic mixtures) with a view to reducing the rates of application and to improving the spectrum of action of the known compounds.
Accordingly, we have found that this object is achieved by the mixtures defined at the outset. Moreover, we have found that better control of the harmful fungi is possible by applying the compounds I and the compounds II simultaneously together or separately or by applying the compounds I and the compounds II in succession than when only the compounds I or II are used.
R in formula I is hydrogen or a halogen atom such as fluorine, chlorine, bromine or iodine, especially hydrogen, fluorine or chlorine, in particular hydrogen or fluorine.
In relation to the C.dbd.N double bond, the compounds of the formula I can be present in the E or the Z configuration (in relation to the CO--NHCH.sub.3 group). Accordingly, they can be used in the mixture according to the invention in the form of pure isomers or else in the form of an E/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, in many cases the E isomer being especially preferred.
The C.dbd.N double bonds of the oxime ether groups in the side chain of the compounds I can exist in each case in the form of pure E or Z isomers or as E/Z isomer mixtures. The compounds I can be used in the mixtures according to the invention as isomer mixtures or else as the pure isomers. With a view to their use, compounds I which are particularly preferred are those where both oxime ether groups in the side chain are in the E configuration (E/E).
Due to the basic character of the NH group, the pyrimidine derivatives of the formula II are capable of forming salts with inorganic or organic acids or with metal ions.
Examples of inorganic acids are hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid and hydriodic acid, or sulfuric acid, phosphoric acid and nitric acid.
Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl or naphthyl, which have attached to them one or two sulfo groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which have attached to them one or two phosphoric acid radicals), it being possible for the alkyl or aryl radicals to have attached to them further substituents, eg. p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid etc.
Suitable metal ions are, in particular, the ions of the elements of the second main group, in particular calcium and magnesium, of the third and fourth m
REFERENCES:
Research Disclosure, Apr. 1993, "Mixture of Fungicides and Herbicides" No. 348, 4 page,.
Fraine et al, Pesticide Science, vol. 44, No. 1 (1995) pp. 77-79.
Research Disclosure, Feb. 1993, "Mixture of Fungicides", No. 346, 1 page.
Research Disclosure, Feb. 1995, "Mixture of Fungicides", No. 370, 1 page.
Ammermann Eberhard
Bayer Herbert
Lorenz Gisela
Muller Ruth
Sauter Hubert
BASF - Aktiengesellschaft
Robinson Allen J.
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