SU694043A1 - Phosphorus-containing symm-triazines possessing hesectoacaricidic activity - Google Patents

Description

(54) PHOSPHORUS-CONTAINING SYMM-TRIAZINES, HAVING INSECTIC ACIDITY ACTIVITY

one

This invention relates to the chemistry of organophosphorus compounds, and specifically to phosphorus-containing symmetry triazines of the formula

here d

ABOUT

 -N / NHCHitHiOpvoCe, H5, (1) N

where R is an isopropylamino or diethylamino group having insectoacaricidal activity.

The compounds exhibit a high insecticidal activity against the tracks of the unpaired alkalis and a1 aricidal activity against the spider mites and can be used in agriculture.

A known insecticide and acaricide used in agriculture is carbofos 0,0-dimethyl-5- (1,2-dicarbethoxyethyl) dithiophosphate 1.

Known derivatives of sim-triazine, having as a substituent organophosphate residue 2.

Closest to the invention is saifos (0,0-dimethyl-5- (4,6-diamino-1,3,5-triazinyl-2-methyl) -dithiophosphate) 3.

However, this drug has a narrow spectrum of action and is effective mainly for fighting aphids.

The purpose of the invention is to expand the range of insecticides and acaricides and their spectrum of biological action. This is achieved by the known derivatives of sim-triazine of formula (1).

The compounds practically do not inhibit cholinesterase (CE) (when the concentration of CE is inhibited by 8-20%), while metaphos and carbofos inhibit CE by 50 ° / o at a concentration of 10%, and chlorophos - by 100% at a concentration of 10% . Thus, the proposed compounds can be used to combat insect races resistant to organophosphorus compounds.

The known organophosphorus compounds of the formula () are obtained by reacting hydroxyethylaminotriazines with O-phenylmethylphosphonic acid chlorides.

The process is carried out at a temperature of 40-50 ° C in benzene in the presence of an acceptor of hydrogen chloride, such as triethylamine, in an organic solvent for 2-4 hours. The IR spectra of the compounds obtained, measured in KBr tablets, contain absorption bands at 1245- 1250 (), 3245-3250 cm (NH), 158 {1410, 805 (triaznnuyu ring) - and do not contain the absorption band of the OH-groups, Example 1. Preparation of 0- (2-chloro-4-isopropylamino-simm-triazin-6 -yl) ethylamino-0-phenylmethyl-6-phonate. To a solution of 2.3 g (0.01 mol) of 2-chloro-4-isopropylamine-b-ethanolamine-simm-triazine and 1.01 g (0.01 mol) of triethylamine 130 ml of a water-free benzol with an added solution of 1 , 9 g (0.01 mol) of 0-phenylmethylphosphonic acid chloride in 20 ml of anhydrous benzene. The mixture was stirred at 40 ° C for 2 hours. The precipitate of triethyl amine hydrochloride was filtered off and washed with anhydrous benzene. The organic filtrates are combined and the solvent is distilled off. 3.15 g of 0- (2-chloro-4-hzopropylamino-simm-triazin-6-yl) -ethylamino-0-phenylmethylphosphonate are obtained, yield 82%, mp. Yub-108 ° C (from cyclohexane J. Found, a / c: C 46.93; H 5.56; C1 9.01; N 18.13; P 8.43; C 46.68; H5.48; C19, 12; N 18.08; P 8.41. Vychnmeno, o / o: C 4.69; .H 5.48; C; 9.18; N 18.14; P 8.02 Molecular mass 385.80 (calculated) .385 (determined by mass spectrometry). Example 2. Preparation of 0- (2-chloro-4-diethylamine-snmm-tr "azin-6-yl) -ethylamino-0-phenylmethylphosphonate. In terms of; similar to the preparation 0- (2-chloro-4-isopropyl lamino-simm-triazin-6-yL) ethylamino-0-phenylmethylphosphonate, from 2.46 g (O.Oi mol) 2-chloro-CH 2 and ethylamino-6-ethanolamine-mmmm-triazine, 1.9 g (0.01 moleconnected

1and

.CHj

 II

1. iCjH NH- -NHCHjCHjOP: OCgHsS

2- (jH5) jKr-kA- IHCHiC HjOP

Malathion

Death,% of the concentration of compounds,% d.n.

caterpillar neparogo

silkworm yes

0.01

100

97 0-phenylmethylphosphonic acid chloride and 1.01 g (0.01 mol) of triethylamine in 150 ml of anhydrous benzene, you get 3.60 g of 0- (2-chloro-4-diethylamino-simm-triazin-6-nl) ethylamino-0- phenylmethylphosphonate, yield 90%, so pl. 77-79C (from cyclohexane). Found,%: C 47.76; H 5.86; C1 8.76; N 17.38; R 7.39; C 47.69; H 5.68; C.I 8.65; N 17; 46; R 7.62 CieHijCINeOjP. Calculated,%: C 48.06; H 5.79; C1 8.86; N 17.52; R 7.75. Molecular weight 399.83 (calculated), 399 (determined by mass spectrometry). Example 3. Caterpillars of non-pair silkworm (Portl) etria disper (spraying method). Caterpillars of age II (5-6 days after the first shedding) are placed in glass cups for spraying with a volume of 150 ml and 20 shchuks in each cup. Spraying is carried out with water-acetone or alcohol solutions of the compounds at a concentration of 0, at a flow rate of 35 ml / m. The experience is set in duplicate. Accounting, death of the caterpillars is carried out after 24 hours. Spider mites (Tetranychus urticae Koch). Cutting leaves with mites on them is sprayed with 2.5 ml of a mixture of an acetone solution With water, an emulsifier and a test substance at a concentration of 0.6%. Accounting is carried out after 48 hours. The test results are shown in the table. Data on insecticidal and acaricidal activity of matches

five- - , . 6

Claims (2)

Claims. Information sources, , Phosphorus-containing symmetry triazines of the general formula p. . , Schrader G. New organophosphorus4 t g JIt .1Я .. & L -. „1 l 1 KP About ... Kie insecticides. M ,. "World. 1965, p. 160 Hy NHCHitHiOPxoCjHs. 2. US Patent No. Zd38985. cl. 71-93, where I - isopropylamino-, nli diethylamioiobublnk. 1976. oa a sh group possessing insecto-acarynd 3. Pat of France J 1219238, cl. And 01, activity. publish 1965. “94043. accepted in expertise