Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-11-20
1999-12-07
Stockton, Laura L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514241, 514252, 514256, 514363, 514364, 514384, 514342, 544189, 544198, 544238, 544333, 5462687, 5462694, 5462724, 5482642, 5482644, A01N 43653, C07D24912
Patent
active
059984465
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to compounds of the general formula I ##STR2## where the index and the substituents have the following meanings: R is cyano, halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy; each other if n is 2; nitrogen atoms and one oxygen or sulfur atom and having attached to it an unsubstituted or substituted phenyl ring or an unsubstituted or substituted 6-membered heteroaromatic ring which, in turn, has one to four nitrogen atoms.
Moreover, the invention relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling animal or fungal pests.
The literature discloses hetaryloxymethylenephenylcrotonates in which the heteroaromatic ring can have attached to it a phenyl group in the Het-position (EP-A 513 580).
However, it was an object of the present invention to provide compounds having improved characteristics.
Accordingly, we have found that this object is achieved by the compounds I defined at the outset. Moreover, there have been found processes for their preparation, compositions comprising them and their use for controlling animal or fungal pests.
The compounds I are prepared by a method sismilar to those described in the literature quoted at the outset by reacting a compound of the formula II with a benzyl compound of the formula III in an inert organic solvent in the presence of a base. ##STR3## L in formula III is a nucleophilically exchangeable leaving group, such as halogen (eg. fluorine, chlorine, bromine and iodine, in particular chlorine, bromine and iodine) or a sulfonyl radical (eg. methylsulfonyl, trifluoromethylsulfonyl, phenylsulfonyl and methylphenylsulfonyl).
This reaction is conventionally carried out at from 0.degree. C. to 120.degree. C., preferably 20.degree. C. to 90.degree. C.
Suitable solvents are 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, alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide and dimethylformamide, particularly preferably tetrahydrofuran, acetonitrile, acetone and dimethylformamide. Mixtures of these can also be used.
Suitable bases are, generally, inorganic compounds such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates, such as sodium hydrogen carbonate, alkali metal and alkaline earth metal alcoholates, such as sodium methanolate, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, furthermore organic bases, eg. tertiary amines, such as trimethylamine, triethylamine, triisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.
Sodium hydride, potassium carbonate and sodium methanolate are particularly preferred. The bases are generally employed in catalytic amounts, but they can also be used in equimolar amounts, in an excess or, if desired, as the solvent.
The educts are generally reacted with each other in equimolar amounts. It may be advantageous for the yield to employ an excess or substoichiometric amount of II based on III.
The reaction mixtures are worked in the customary manner, eg. by mixing with water, separating the phases and, if desired, purifying the crude products by chromatogr
REFERENCES:
patent: 4937372 (1990-06-01), Wenderoth et al.
patent: 5298527 (1994-03-01), Grammenos et al.
patent: 5416068 (1995-05-01), Grammenos et al.
Ammermann Eberhard
Gotz Norbert
Grammenos Wassilios
Konig Hartmann
Lorenz Gisela
BASF - Aktiengesellschaft
Stockton Laura L.
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