SU436818A1 - The method of obtaining 0, -substituted derivatives of aryl (alkyl) carbamoyl (thiocarbamoyl) - - (1-oximino-1,2,3,4 tetrahydronaphthyl) -2-hydroxylamines - Google Patents

Description

I

This invention relates to a process for the preparation of previously unknown O-substituted derivatives N-aryl (alkyl) carbamoyl (thiocarbamoyl) N- (1-OKCHMHHO-1,2,3,4-tetrahydronaphthyl-2) hydroxylamines of the general formula

OCOXR

i-N-CX-NHR I OM

where R and R is aryl or alkyl,

CiH is an oxygen or sulfur atom that can be used as biologically active compounds in agriculture.

A known method for the preparation of O-carbalkoxyN-alkylcarbamoyl-N-arylhydroxylamines by reacting M-alkylcarbamoyl-Marylhydroxylamine with chlorogolic acid esters with biological activity. However, there is no information in the literature about the method of obtaining compounds of the general formula given earlier, which has greater biological activity than the indicated compounds.

A method is proposed for preparing compounds of the general formula not described in the literature.

by the interaction of N - aryl (alkyl) carbamoyl (thiocarbamoyl) -: M- (1-oximino - 1,2,3,4-tetrahydronaphthyl-2) hydroxylamine with alkyl (aryl) chlorocarbonate or alkyl (aryl) thiol chlorocarbonate in inert organic medium solvent, for example dioxane or tetrahydrofuran, in the presence of an acceptor of hydrogen chloride, for example triethylamine or pyridine.

Example 1. To a suspension of 0.01 m of the N-alkylcarbamoyl derivative of L- (1-oximino1, 2,3,4 - tetrahydronaphthyl-2) -hydroxylamine in 100 ml of dioxane add 0.012 m of triethylamine and 0.012 m of alkyl chlorocarbonate

10-15 ml of dioxane at 20-25 ° C. The reaction mixture is moved for 2-3 hours. The hydrochloric triethylamine is then filtered off and the dioxane is distilled off in vacuo. The residue is recrystallized from ethyl acetate. Compounds 1 to 7 listed in the table are obtained. The yield is 80-90%.

Example 2. To a solution of 0.01 m N-arylcarbamoyl-M- (1-oximino - 1,2,3,4-tetrahydronaphthyl-2) -hydroxylamine in 70-80 ml of tetrahydrofuran, cooled to O-5 ° C, 0.01 m of triethylamine and, with stirring, dropwise, a solution of 0.01 m of alkyl chlorocarbonate in 10-15 ml of tetrahydrofuran at a rate such that the temperature does not rise above 10 ° C. The reaction mass is high

sr s h u ta y

5 tegty and the trieslamine hydrochloride is filtered off and the solvent is distilled off in vacuo. The residual of the method of obtaining O-substitution nronzGp (zl ™) carbamoyl (thiocarb ™ l Dy ™ ™ 1,2D4-tetrahydronaphthyl-2) -hydroxylamines of the general formula NOCOXR D-1Y-MHR -N-CX Nnii 15 b ™ is recrystallized from a crystal. The compounds listed in the table of nods 8-15 are obtained. Yield 60-70%. where R and R are aryl or alkyl, X and X are oxygen or sulfur atoms, characterized in that, N-aryl (alkyl) carbamoyl (thiocarbamoyl) -Y - (1-oximino-1, 2,3,4- tetrahydronaphthyl-2) -hydroxylamine is reacted with an alkyl (aryl) chlorocarbonate (thiol-chlorocarbonate) in the presence of a hydrogen chloride acceptor, triethylamine, in an organic solvent, followed by isolation of the desired nucleus by a known method.