SU1547689A3 - Insecticide - Google Patents

Abstract

The invention relates to chemical plant protection agents and permits an increase in insecticidal action due to the fact that the agent contains, in wt%: a compound of the general formula @ -CONHCONH- @ -OCF ₂ CHFCF ₃ , where R ₁ = CL, F, OCH ₃

R ₂ = H, CL, F, OCH ₃ , or its NA-salt, as an active substance 25-75%, as a surfactant - a mixture of compounds selected from the group including sodium lignosulfonate, sodium lauryl sulfonate, sodium diisobutyl naphthalene sulfonate and octylphenol polyethylene glycol ether, 8-15%, as a filler - highly dispersed silicic acid or its mixture with kaolin 10-67%.

Description

This invention relates to chemical plant protection products, specifically to an insect control agent.

The purpose of the invention is to increase the insecticidal effect.

The invention is illustrated by the following examples.

PRI me R 1.

but. Preparation of 2,5-Dichloro-4- (1,1, 2,3,3,3-hexafluoropropyloxy) aniline.

hi g-acetylamino-2,5-dichlorophenol is stirred in an autoclave together with 151 g of a 90% potassium hydroxide solution and 130 ml of dimethylformamide. Then, 75.8 g of hexafluoropropylene was introduced into the closed autoclave under pressure. The mixture is stirred for 20 hours at 70 ° C at a pressure that has been set in the autoclave. After cooling, the mixture is evaporated on a rotary evaporator, after which the resulting residue is dissolved in methylene chloride. The resulting solution was washed with water, dried over sodium sulfate and evaporated. The crude product obtained as a residue is chromatographed on a column filled with silica gel (1 m long, 10 cm in diameter) using a mixture of toluene and acetone (11: 1) as an eluent. The result is k-acetylamino-2,5-dichloro-1 - (1, 3,3,3-hexafluoropropyloxy) benzene in the form of a light yellow colored crystalline substance

S

About 00

with

cm

3/15

(mp. 93-95 ° C). 26 g of the obtained compound together with AND 0 ml of ethyl alcohol and 35.6 ml of 37% hydrochloric acid are incubated for 10 hours at the boiling temperature of the reaction mixture under reflux. The reaction mixture is then evaporated, diluted with a mixture of water and ice, after which a weak alkali is produced.

chivanie. The product is extracted from the mixture with methylene chloride. The organic phase of the extract is washed with water, dried over sodium sulfate and evaporated. The residue obtained is purified by distillation. In this way receive the compound of the formula

01

0SGG- SNG-

s as a colorless liquid with boiling point, §1-83 ° С / 0.05 mm Hg.

OCF2-CHF-CF3

 -co -t- with -tg- g

in the form of a crystalline powder, Be. Similarly, color logo compounds are obtained with a mp. 17 -175sC (connection 2-11 below: nyenie 1)

 Connection T ™ 65-16, C

at). Preparation of M- (2, L-trifluoromebzolyl) -and - (2,5-dichloro-4- (1,1,2,3,3,3-hexafluoropropyloxy) -phenyl-urea.

B, 1 g of 2,5-dichloro-M1, 1, 2, 3, 3, 3-hexafluoropropyloxy) aniline is dissolved under stirring in 50 ml of dry toluene, after which the prepared solution is at room temperature under conditions that exclude the presence of moisture. , mixed with 2.62 g of 2,6-difluorobenzoyl isocyanate dissolved in 10 ml of dry toluene. The mixture is then stirred for an additional 10 hours at room temperature. Thereafter, approximately 75% of the solvent is distilled off from the reaction mixture on a rotary evaporator, the precipitated product is filtered off on a suction filter, washed with a small amount of cooled toluene and hexane, and then dried under vacuum.

8 the result is a compound of the formula

OCF2-CHF-CF3

 // - co - im - co-im-O - o - CFz (3iF (JF3

 ci

C1C1

 JKCQ-im-CO-H-O-O-CF CHF CF3

 Cl

Cl

Q -co-im - with o-m

5 OCH3Cl

G so-van-so-zga

188-190

Cl

YZ-Y5 ° C

0 Cr2CHFCF3

135-137 ° C

0-CF2CHFCF3 Cl

 SO-YAN-SO-YAN

osn3

8OCH3c

O-co-ira-co-NH

OCH3

9ClCl

co-ga-co-mi

OCH3

with). Preparation of the sodium salt of compound 1. 9.85 g (2,6-difluorobenzyl) - to - (2,5-dichloro-4) -1,1,2,3,3,3-hexa-fluoropropyl oxy- (phenyl) -Urea suspended in 20 ml of absolute methyl alcohol. To the prepared suspension with stirring is added

 F

.O- with-zg-with-kn F F ha

about

in the form of a colorless crystalline substance with so pl. 169-171 ° C at decomposition (compound 10).

C1

with -N - with -tega-oh - CF, CHFCF

NU

below 140 ° C / s decomposition.

EXAMPLE 2. Preparation of preparations using biologically active substances corresponding to example 1 (see Table 1).

diluted with water to sia any desired

Experience 1. Insectic Spodoptera littoral

Benzoyl ureas 1-11 grind from 2, 1a into powder for diluting with water to a concentration of 0.8 sprinkle liberally to dry the mixture

The biologically active substance is thoroughly mixed with additives, after which the mixture is stirred in a mill. The result is a wettable powder, which can be

0-CK2-CHFCF3 Cl

162-1634

0-CF2-CHFCF3 Cl

190-191 ° C

0-CF2-CHFCF

Cl

drop a solution of 0.3 g of sodium in 30 ml of absolute methyl alcohol. The resulting clear solution is then evaporated. The product obtained as a residue is dried at room temperature under vacuum. The result is a compound of the formula

-0-CF2CHFCF

Cl

i

Similarly, the following salt of compound 2 is obtained, which corresponds to the following formula (compound 11). Mp.

C1

diluted with water to obtain a suspension of any desired concentration.

Experience 1. Insecticidal effect on Spodoptera littoralis.

Benzoyl ureas A and compounds 1-11 are ground according to Example 2, 1a into a powder for spraying and diluted with water to obtain a mixture of 0.8 pp.m. Cotton is plentifully sprayed with this mixture. After drying the mixture on each plant

cotton is placed on 10 larvae of Spodoptera littoralis. After 6 days at and 60% relative humidity, percent mortality of larvae is determined.

At the same time receive the results given in table 2.

Experience 2. The effect on Heliothis virescens.

Benzoyl ureas A and 1 st grind according to example 2, 1c to a powder for spraying. The test is performed in the same way as Test 1. However, the concentration of the active substance in the spray mixture is 1.5 p-p.m. On soybeans place the larvae of Heliothis virescens.

CO — NH — CO — NH 4 Vo — CF, —CHF — CF,

Claims (1)

Claims; Insecticidal agent in the form of a wettable powder containing the active substance, surfactant and filler, о tBi ( PG CO-BN-CO-2SH - SU Q-CF2- R where R, -C1, F, OCH3; , Cl, F, OGH3, or its Na-salt, as a surfactant — a mixture of compounds selected from the group including sodium lignosulfonate, sodium lauryl sulfonate, diisobutylnaphthalene sulfonate, octylphenol polyethylene glycol ether, as a filler - highly dispersed At the same time receive the results given in table 3. Experience 3. The effect on Plutella xylostella. Benzoyl urea A and compounds 1-11 are ground to a powder for spraying, as described in Example 2, 1c. The test was performed in the same way as Test 1, with an active substance concentration of 0.8 p.r. Plutella xylostella (2- and 3-stage) larvae and Chinese cabbage are used as the test models. Mortality is determined after 5 days. At the same time receive the results given in table. Compound A has the formula , kicking with the fact that, in order to increase the insecticidal effect, it contains a compound of the general formula € 1 Chloric silicic acid or its mixture with kaolin with the following content of components, wt.%: Active., substance Surface-active agent Performer 25 - 75 8 - 15 10 - 6 1b4 68th Continuation of table 1