Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1997-08-11
1999-07-27
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514613, 514617, 514618, 514619, 514622, 514624, 514625, 514628, 514629, A01N 3718
Patent
active
059291192
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a composition which is suitable for controlling fungal pests, comprising customary additives and an effective amount of a p-hydroxyaniline derivative of the general formula I ##STR2## where the radicals have the following meanings: R.sup.1 is hydrogen, C.sub.1 -C.sub.8 -alkyl which can be partially or fully halogenated and/or can have attached to it one or two of the following groups: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.7 -cycloalkyl, C.sub.5 -C.sub.7 -cycloalkenyl, it being possible for the cyclic groups, in turn, to have attached to them one to three halogen atoms, C.sub.1 -C.sub.3 -alkyl groups and/or C.sub.1 -C.sub.3 -alkoxy groups, and aryl which can be partially or fully halogenated and/or can have attached to it one to three of the following substituents: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio, being possible for these radicals to be partially or fully halogenated and/or to have attached to them one to five of the following groups: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and aryl which can be partially or fully halogenated and/or can have attached to it one to three of the following substituents: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and C.sub.1 -C.sub.4 -alkylthio; -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -haloalkoxy.
The invention furthermore relates to the use of the compounds I and of the compositions comprising them for controlling fungal pests, and to the use of the compounds I for the preparation of the compositions.
2. Description of the Background
The literature discloses alkylcarboxanilides which are fungicidally active (U.S. Pat. No. 3,849,478, U.S. Pat. No. 3,958,006, EP-A 293 718 and JP-A 345 751/93).
EP-A 339 418 furthermore discloses 4-hydroxyanilides, but these are not yet satisfactory with regard to their fungicidal action.
SUMMARY OF THE INVENTION
It was an object of the present invention to provide compositions which have an improved action against a wider spectrum of fungal pests.
Accordingly, we have found that this object is achieved by the compositions defined at the outset.
We have also found the use of these compositions and of the compounds I for controlling fungal pests and the use of the compounds I for the preparation of the compositions.
DETAILED DESCRIPTION OF THE INVENTION
EP-A 653 417 and EP-A 653 418 disclose the compounds of the general formula I and their preparation. In these documents, the compounds are described as intermediates for fungicidal o-acylated p-hydroxyaniline derivatives.
The hydroxyaniline derivatives of the general formula I are obtained by reacting a p-hydroxyaniline of the formula II in a manner known per se (cf. DE-A 32 02 100; EP-A 339 418) with a carbonyl derivative of the formula III in an inert organic solvent in the presence or absence of a base. ##STR3##
In formula III, the variable X is halogen, in particular chlorine, bromine and iodine, or a leaving group customary in acylation reactions, eg. R.sup.1 --CO--O.
The reaction is conventionally carried out at from -70 to 140, preferably 0 to 110, .degree.C.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide and dimethylformamide.
Mixtures of these ca
REFERENCES:
patent: 4666943 (1987-05-01), Noguchi et al.
patent: 5059623 (1991-10-01), Kruger et al.
patent: 5492931 (1996-02-01), Krueger et al.
Ammermann Eberhard
Lorenz Gisela
Wagner Oliver
BASF - Aktiengesellschaft
Robinson Allen J.
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