Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1997-10-30
1999-11-16
Shah, Mukund J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514256, 514277, 514374, 514378, 514438, 514452, 514461, 514475, 514524, 514532, 544335, 546342, 548236, 548247, 549 79, 549362, 549501, 549549, 558252, 558253, 558256, 558257, 558260, 560 9, 560 20, 560 21, 560 23, 560 24, 560 27, 560 29, 560 31, 560 32, 560 45, 560 47, 560 48, 560 49, A01N 4340, A01N 3710, A01N 4354, A01N 4384, C07D21355, C07D23926, C07D23934, C07C 69618
Patent
active
059859199
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to (het)aryloxy-, -thio- and -aminocrotonates of the formula I ##STR2## where the substituents have the following meanings: U is oxygen (--O--), sulfur (--S--) or amino (--NH--); [--N(alkyl)-]; -alkyl; C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio; via an oxy, mercapto, amino, carboxyl or carbonylamino group.
The invention furthermore relates to processes for the preparation of these compounds, to compositions comprising them, and to their use for controlling animal pests and fungal pests.
The literature discloses (het)aryloxy-, -thio- and -amino-.beta.-alkoxyacrylates which are fungicidally active (EP-A 212 859; EP-A 383 117; EP-A 471 261; EP-A 503 436; EP-A 584 625). EP-A 409 369 furthermore describes herbicidally, growth-regulatory and fungicidally active hetaryloxy- and -thiocrotonates in which the hetaryl ring is either a pyrimidin-2-yl ring or a 1,3,5-triazin-2-yl ring.
It was an object of the present invention to provide compounds having improved properties.
We have found that this object is achieved by the compounds I which are defined at the outset. We have also found processes for the preparation of these compounds, compositions comprising them, and their use for controlling animal pests and fungal pests.
The compounds I can generally be prepared by the processes described in the literature cited.
The compounds I where V is oxygen or sulfur are preferably obtained by reacting a corresponding alcohol or a corresponding thiol of the formula IIa with a crotonate of the formula III in a manner known per se (J. Chem. Soc. 1963, 4210) in the presence of a base. ##STR3##
In formula III, L is a nucleophilically replaceable leaving group such as halogen (eg. chlorine, bromine and iodine) or a sulfonate (eg. trifluoromethylsulfonate, phenylsulfonate and p-methylphenylsulfonate).
This reaction is conventionally carried out at from 0.degree. C. to 200.degree. C., preferably 0.degree. C. to 150.degree. C., in particular 10.degree. C. to 100.degree. C., in an inert solvent or diluent.
Suitable solvents or diluents are ether, chlorobenzene, dioxane, anisole and tetrahydrofuran, methyl ketone, tert-butanol, acetonitrile, dimethylformamide, dimethyl sulfoxide and 1,3-dimethyltetrahydro-2(IH)-pyrimidinone (DMPU). 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 and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal hydrides 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 carbonates and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate, and also alkali metal hydrogen carbonates such as sodium hydrogen carbonate, organometal compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal alcoholates 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.
Potassium carbonate, potassium hydroxide and sodium hydrogen carbonate are particularly preferred.
The bases are generally 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 II in an excess
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Ammermann Eberhard
Grote Thomas
Harreus Albrecht
Kirstgen Reinhard
Konig Hartmann
BASF - Aktiengesellschaft
Coleman Brenda
Shah Mukund J.
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