SU858560A3 - Method of preparing n-carbamoylethyloxanylate - Google Patents

Abstract

A composition of matter is described herein which has herbicidal activity and methods of use. The composition is defined by the following generic formula wherein X and Y are independently selected from the group consisting of chloro, bromo, and trifluoromethyl; n is either 0 or 1; m is either 0 or 1; and R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive, or R and R1 taken together is selected from the group consisting of , , and .

Description

(54) METHOD OF OBTAINING N-CARBAMOILETHYLOROXYANILATE

The invention relates to methods for the preparation of new compounds, specifically N-carbamoylethyloxanilate of the general formula of HCO-C-oCiHf -, where X and Y are selected from the group consisting of chlorine, bromine and trifluoromethyl atoms, the type is equal to, or 1, R and R are independently selected from the group consisting of lower alkyl and lower alkoxy; from C to C / R and R, together with the atom N form g- / -L. -CH,. These are used as herbicides in agriculture. The proposed compounds, in comparison with the known similar actions, have a greater herbicidal activity. A chemical reaction is known to produce urea derivatives by condensing a substituted urea with halogen derivatives. However, the use of B as initial substances of g-ethyloxalyl halide of the formJ s C HS-O-C-C-Z where Z is selected from the group consisting of chloro or bromo substituents and a urea derivative of the formula /. m / Jm (where X, l, m, n, R and R have the indicated meanings, allows to obtain new compounds with improved herbicidal properties. The purpose of the invention is to obtain new compounds, specifically N-carbamoyl ethyloxanilate of general formula I. The goal is achieved by that, according to the method of producing H-carbamoylstiloxanlate, a urea derivative of formula II is reacted with an ethyl oxalyl halide of formula III in an inert solvent at 40-65 C. Typically, the process is carried out in methylene chloride or p.poroform. at a temperature close to the boiling point of the solvent used. The solvent and operating temperature are chosen so as to avoid possible thermal decomposition of the product. In the reaction, besides the required N-carbamoyl ethyloxanylate, hydrogen halide is also formed - either chloride or hydrogen bromide, depending on what ethyl oxalyl halide is use C. In order to ensure the removal of side hydrogen halide, atmospheric pressure or slightly lower pressure is maintained. Example 1: Preparation of M- {dimethylcarbamoyl) -ethyl-3-trifluoromethylox nilate (compound 3 of the table), 116 g (0.5 mol) of 1,1-dimethyl-3- ( 3-trifluoromethylphenyl) -urea, 250 ml of methylene chloride and 82 g (0.6 mol of ethyl oxalyl chloride. The resulting solution is refluxed for 7 hours, for which all the urea reacts. After distilling off the solvent and excess Ethyl-oxalyl- (4-chlorophenyl) -c, N-dimethylS H ClN O. urea 24

1- (3,4-Dichlorophenyl) -1-ethyl-oxalyl-3, 3-dimethylurea

1- (L-TRIFTOR

methylphenyl) -1-ethyloxalyl-3, 3-dimethylurea

1- (3,5-Dichlorophenyl) -1-ethyloxalyl-3, 3-tetramethyleneurea

0-1 4-ClCHjCHj Ace-1,5327 - 27.5

tone

1 1 4-ClCH CHj

105-91.0 107

97- 97.0

0-1 3-С1СНэСНд 99

but

1 3-C1 1 5-C1

261- 85.4 285 th acid chloride, 161 g of a white solid with a m.p. BT-BE C containing, according to analysis, 96% of the pure product / and the yield is 97%. Example2. Preparation of M- (dimethylcarbamoyl) -ethyl-3, 4-dichloroxanylate (Compound 2). 902 g (3.88 mol) of 1- (3 4-dichlorophenyl) -dimethylurea and 2 l of dried chloroform are charged to a 5-liter round-bottomed four-necked flask. The mixture is cooled with ice water while slowly adding 610 g (4.46 mol) of ethyl oxalyl chloride. The temperature is maintained below 20 ° C. At the end of the administration of ethyl oxalyl chloride, the reaction mixture is heated at slight reflux for 8-9 hours until the reaction is complete (the reaction is monitored by liquid phase chromatography). The solution is evaporated with stirring to approximately one-fourth of the original volume. A white solid is formed and, after drying, 1.182 g of yield is obtained 91% of the desired compound with a purity of 98% at a temperature of 123-124 ° C. The remaining new compounds are listed in the table.

Claims (2)

Claim 1 3-C11 4-C1 OCH ₉ CH ₃ Viscous oil 31,2 3-C11 3-C1 3-C1 4-Vg OCH _s CH _e The same 1.5303 83.0 1 4-C1 CH Acetone Semi- 81.0 ^J solid / ~ A 1 4-C1 'O \ ___ / —it96-99 45.3 The method of obtaining N-carbamoylethyloxanilate of the General formula 1 * I characterized in that the urea derivative of the formula and R have the indicated where X values, are reacted with an ethyloxalyl halide of formula 11 40 С ₂ Н ₅ - О-с - CZ co о о II II Я-С ~ С-0С _g Н; I / I in, where X and 'Y are selected from the group consisting of chloro, bromo substituents, and trifluoromethyl, pi m is either 0 or 1; R and R4 are independently selected from the group consisting of lower alkyl and lower alkoxy group from C 4 to C _3, or R and R ^ together with the N atom form a o. where Z is selected from the group consisting of chlorine or bromo substituents in an inert solvent at .40-65 ° C. 2. The method according to claim 1, characterized in that methylene chloride or chloroform is used as an inert solvent.