SU524803A1 - -Pirrolidinoethyl esters of dialkyl (thio) phosphoric acid - Google Patents

Description

undergo hydrolysis than the well-known substituted pyrrolidides of phosphorus acids and, on the other hand, their synthesis is simpler than the synthesis of pyrrolidides with the ether o (.-chloropropenyl radical, and the starting ones are more up to

Evaporation at 18-20 ° С

(Mkg / cm hour)

(CjH, 0) .POCH,

1.1 372 ,, - SNG-SNG

Sn, -Sn, I

3.5

(CjH, 0), POCH2CH2N Reference (С2Н5) 2КС {0) -С5Н4СНз 3.5 DETA

(CHJe lClOl-CgHs

0.6 Hexamide

It follows from the table that, by the effectiveness of the P-pyrrolidinoethyl esters of dialkylphosphoric and dialkylthiophosphoric acids, they are superior to DETA and approach or equal to hexamide.

Example 1. Getting | i -pyrrolidinoethyl ether of diethylphosphoric acid. To a benzene solution of 5 g of Ji-pyrrolidinoethanol, 6.7 g of carbon tetrachloride and 4.5 g of triethylamine add 6 g of diethylphosphorous acid with stirring and cooling the reaction mass to 2 ° C. After removing hydrochloric triethylamine, chloroform and the solvent twice. distilled in vacuum to obtain 8.3 g (77% of the substance with m.p. 87 / 0.04 mm,

d4 ° 1.0815. 1.4454. Found: WR 61.79, P 12, 16, N5.29 Calculated for CioH2aNOi, P MR 62, 12,

R 12.35, Y5.57.

Example 2. The preparation of diprophosphoric acid ji-pyrrolidinoethyl ester. To a benzene solution of 6.9 g Ji

-pyrrolidinoethanol, 9.4 g of carbon tetrachloride, 7.1 g of triethylamine add 10 g of dipropylphosphorous acid at 20 ° C, stirring and cooling the reaction mass. After removing triethylamine hydrochloride, chloroform and solvent, the residue is distilled twice in vacuo, to obtain 11.4 g (b 7% of theor.) Substance with m.

feet. The repellent activity of | L-.Shprolidino-ethyl esters of dialkylphosphonic and dialkylthiophosphoric acids and their evaporation in comparison with the reference ones: repellents are presented in the table.

The duration of the deterrent effect over time intervals the remainder- (sec) and the average (M) action (day) 30 60 120 180 (m)

99 100 100 98.8 More than 150

96

80 97 100 100 94.2

91 95 99 99 96.0 More than 15О

.20.

kip 98 / 0.04 mm., D, 0458, 4470 Found MR 71, 29, R 11.05, N 5.12. Calculated for C H NO.P MR 71.36, P 11.11, N5.

Example 3. Preparation of p-pyrrolidinoethyl dibutyl phosphoric acid. To a benzene solution of 5.4 g of ji-pyrrolish-ethanol, 7.1 g of carbon tetrachloride, 5.9 g of triethylamine, 9 g of dibutyl phosphoric acid are added dropwise while stirring and cooling the reaction mass. After removal of the solyric acid triethylamine, chloroform, and solvent, the residue is twice distilled in vacuo to yield 11.5 g (81% of theor.) Of a substance with a boiling point. 114-115 ° / 0.04 mm. , 0208, Ti 1.4474 found: MR 8О, 39, Р 10, 12 N4.44. Calculated for C H NO “P MR 80.59, P 10.1 N4, 56

Example 4. Preparation of diisobutylphosphoric acid P-pyropropyldioethyl ester. To a benzene solution of 11 g of 1H -nHj rolidinoethanol, 6.5 g of carbon tetrachloride, 5.1 g of triethylamine, are added dropwise 8 g of diisobutyl phosphoric acid, while stirring and cooling the reaction mass. After removal of triethylamine hydrochloride, chloroform and solvent, the residue is distilled twice, 9.8 g (78% of theor.) Are obtained with

, O1655

m.p. 105-1О6 / 0.03 mm repellent 1OO 100 100 100 100 About 60