CS224216B1 - 0-alkyl-s-chloromethyl-n-alkylamidothiophosphates and method of preparing same - Google Patents

Description

The present invention relates to O-alkyl-S-chloromethyl-N-alkylaidothiophosphate and methods of preparation.

The O-alkylthio (dithio) alkylphosphonic acid (T1) S-chloromethyl esters of O-alkylthio-thiophosphoric acid (1) and S-chloromethyl esters of O-alkylthio (dithio) -alkylphosphonic acid (Tl) are known from the literature.

WITH

- x - 0¾ - σι / 1

R / O / N

Y-OHg / 11 /

Cl as ρδάηβ insecticides / US Pat. No. 3,896,219, U.S. Pat. 1,015 * 794 (from which O, O-diethyl-S-chloromethyldithiophosphate) is used in practice. 536,070 /.

They have now been found S-chloromethyl-O-alkyl-N-alkylamidotiofosfáty of the formula III ^{R @ 1} ° - S - OH ₂ - CL / 111 /

R ² NH 4

Wherein R and R are the same or different alkyl having 1 to 4 carbon atoms. Said compounds are effective as insecticides and acaricides.

At the same time, a process for the preparation of the compounds of formula (111) by reacting bromochloromethane with an O-alkyl-N-alkylamidothiophosphoric acid salt of Seobeonic Formula IV was found,

R ¹ 0 - _p

R ² NH 4 q

SM / IV /

2 wherein R and R are as defined above, M represents sodium, potassium or ammonium in an organic solvent medium or in a mixture.

224 218 an organic diluent with water, preferably in the presence of a catalyst such as triethylbenzylammonium chloride, tetrabutylammonium bromide, tetraethylammonium bromide and the like at a temperature of 40 to 100 ° 0.

Example 1

To 20.5 g of O-ethyl-N-isopropylamidothiophosphoric acid sodium salt (0.1 mol) in 100 ml acetonitrile was added 25.8 g bromochloromethane (0.2 mol) and the reaction mixture was stirred at reflux for 4 hours. The precipitated sodium bromide was collected by filtration, acetonitrile was distilled off from the filtrate under reduced pressure, and the residue 21.8 g was purified by crystallization from hexane. A white crystalline solid was obtained with mp > 42-43 ° ^g

6.05% N 13.84% S 6.11% N 13.96% S

Analysis for 0 ₆ H ₁₅ 01N0 ₂ PS Off: 13.37%P 15.30% 01 / mh: 231.66 / Find: 13.52% P 15.28% 01

The structure of the compound was confirmed by 10 spectra and 3193 cm ^-1 1239 and 1216 cm ^-1 in 001.:

^Ο / Β-Η / ^{! 3400} ^ / P0 / P0-0 / P-00 /

J / P-N / P-SO /

1027 om

955 cm

891 cm

577 and 541 cm

Example 2

To 25.8 g of bromochloromethane (0.2 mol) in 60 ml of toluene was added a solution consisting of 22.1 g of O-ethyl-N-isopropylamidothiophosphoric acid potassium salt (0.1 mol) with stirring at 70 ° C for 20 minutes. 0.1 g triethylbenzylammonium chloride (0.005 mol) and 50 ml water. After the addition, the reaction mixture was stirred at reflux for an additional 1 hour. After cooling, the aqueous layer was separated from the toluene layer from which toluene was distilled off under reduced pressure. The distillation residue (21.6 g) was purified by crystallization from heptane. A white crystalline substance with m.p. = 42-43 °

Claims (3)

1 / O-alkyl-S-chloromethyl-N-alkylamidothiophosphates of formula III R 2 R ² NH; p - S - ch ₂ - 01 ° / 111 / Where R and R are the same or different alkyl and 1 to 4 carbon atoms; 2 / A process for the preparation of compounds according to claim 1 characterized in that the salt is reacted with bromochloromethane-alkyl-N-alkylamidotiofosforečnej of the formula IV ^{R @ 1} ° '- p - SM / IV / Wherein R and R are as defined above, M represents sodium, potassium or ammonium in an organic diluent or in an organic diluent / water mixture at a temperature of 40 to 100 ° C. 3. The process according to claim 2, wherein the reaction is carried out in the presence of a catalyst from the group of quaternary ammonium salts.