Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-04-20
2000-05-09
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514439, 514440, 548217, 549 60, 549 65, 549 66, 549451, A01N 4376, A01N 4326, C07D26304, C07D33332
Patent
active
06060493&
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to compounds of the general formula I ##STR2## where the indices and the substituents have the following meanings: R.sup.1 is C(CO.sub.2 CH.sub.3).dbd.CHOCH.sub.3, C(CO.sub.2 CH.sub.3).dbd.NOCH.sub.3, C(CONHCH.sub.3).dbd.NOCH.sub.3 and N(OCH.sub.3)--CO.sub.2 CH.sub.3 ; -alkoxy; -haloalkyl and C.sub.1 -C.sub.4 -alkoxy; different from each other when n is 2 or 3; C.sub.3 -C.sub.6 -cycloalkyl and phenyl; -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino or a C.sub.1 -C.sub.4 -alkylene chain which is bonded to the C atom directly or via an oxygen, sulfur and/or nitrogen atom and which can have attached to it one or two of the following substituents: oxo (.dbd.O), cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl and heteroaryl.
Furthermore, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling pests or harmful fungi.
Ketones or aldehydes of the phenyl benzyl ethers have been disclosed in the literature as intermediates (EP-A 513 580; DE-A 43 12 637).
It was an object of the present invention to provide novel active ingredients which have fungicidal and pesticidal properties.
We have found that this object is achieved by the compounds I defined at the outset. Furthermore, we have found processes for their preparation, compositions comprising them and their use for combating pests or harmful fungi.
The compounds I are prepared by methods similar to those disclosed in the literature.
For example, compounds I where the radicals X and Y together with the C atom to which they are bonded are an oxirane ring are obtained in a manner known per se [Reactions of Organosulfur Compounds, pp. 101-105, Academic Press, New York 1978; Adv. Org. Chem. 6, 285-388 (1969)] by reacting a carbonyl compound of the formula II with a trimethylsulfoxonium or trimethylsulfonium halide in an inert organic solvent in the presence of a base. ##STR3##
This reaction is usually carried out at from 0.degree. C. to 150.degree. C., preferably 20.degree. C. to 120.degree. C.
Suitable solvents are 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, and also dimethyl sulfoxide and dimethylformamide, particularly preferably dimethyl sulfoxide. mixtures of these can also be used.
Bases which are generally suitable are inorganic compounds such as alkali metal hydroxides and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal hydrides and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, organometallic compounds, especially alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkali metal alcoholates and alkaline earth metal alcoholates such as sodium methanolate, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium. Sodium methoxide, sodium hydride, sodium hydroxide, potassium hydroxide and potassium tert-butoxide are particularly preferred.
The bases are generally employed in catalytic amounts, but can also be used in equimolar amounts, in an excess or, if suitable, as solvents.
The carbonyl compounds required for the preparation of the compounds I are described in the literature cited at the outset. Compounds I where the radicals X and Y are bonded to the C atom via an oxygen, sulfur or nitrogen atom and R.sup.1 is C[CONHCH.sub.3 ].dbd.NOCH.sub.3 are obtained, for example, by reacting a carbonyl compound of the formula II in a manner known per se [Synthesis 501-522 (1981), Synthesis 203 (1983); Carboxylic Ortho Ester Derivatives, pp. 154-164, Academic Press, New York 1970] in an inert organic solvent and optionally an acid and/or an acidic catalyst either a) with an alcohol, thiol an
REFERENCES:
patent: 5145980 (1992-09-01), Wenderoth et al.
Advances in Org. Chem. vol. 6, 1969 285-388.
Int. Jrl. Of Methods in Synthetic Org. Chem. 1981, 501-584.
Int. Jrl. Of methods in Synthetic Org. Chem. 1985, 203-205.
Syn. of Hemiacetals, Acetals, and Ketals 154-164 (1970).
Reactions of Organosulfur Compounds, 1978, 101-105.
Ammermann Eberhard
Gotz Norbert
Grammenos Wassilios
Lorenz Gisela
Muller Bernd
BASF - Aktiengesellschaft
Richter Johann
Sackey Ebenezer
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