SU650480A3 - Insecticide-acaricide - Google Patents

Description

This invention relates to chemical plant protection products, namely insecticide-acaricidal agents based on phenoxybeneyl derivatives. A pesticide is known, whose active ingredient is 3-phenoxybenzyl-l-isopropyl- (3,4-dioximethyenphenyl) acetate 1. However, at low concentrations, this pesticide is not sufficiently active. The aim of the present invention is to find new insect-acaricidal agents having highly biological activity. The goal is achieved by using an insecticoacaricidal agent containing phanoxybenzyl derivatives of the formula I, where R is hydrogen, fluorine, bromine; RJ is hydrogen, fluorine, and R and RJ are different; R.- cyanethenyl; the -VTCH cr CH3 CH, de R and R5 radical are the same and means bromine, methyl or Cd radical CHj de Rg means phenyl, phenyl, substituted yum, fluorine, bromine, methyl, nitmethylenedioxy groups, does R have hydrogen, if Rj is , С1 с: л :: «Жз radical -CH-Pb de Rg has the above-mentioned additive values. The content of the active substance in the tool is from 0.1 to 95 wt.%, The rest is additive. Compounds of formula I are prepared if carbonyl halide of formula II is e-CO-RJ, and where Ra is as defined above. Hat - halogen is reacted with substituted phenoxybeneyl alcohols of the formula III / V. / where R, RJ, R are as defined above. Example 1. CR. l CH-0-CO-CH-H 3 g (0.033 mol) 3- (4 fluorophenoxy).-cyanbenzyl alcohol and 7.6 g (0.33 mol) chloride C-isopropyl-4-chlorophenylacetic acid solution in 150 anhydrous toluene and 2.64 g (0.033 mol) of pyridine diluted in 50 ml of toluene are added dropwise at 25–30 s. Then it is stirred for another 3 hours at. The reaction mixture is poured into 150 ml of water, the organic phase is separated and washed again with water in quantities of 100 ml. Finally, the toluene phase is dried over sodium sulfate and the solvent is distilled off in vacuo. The last remaining solvent is removed by short initial distillation at a bath temperature of 60 ° C /; / 1 torr. Get 13.2 g (91% of the theory of 3- (4-fluorophenoxy) -o6-cyanbenzyl-o-isopropyl-4-chlorophenylacetate as a yellow oil;, 5549. Example 2. Shg-0-CO-CH Gamma V / H YazS CH, g (0.035 mol) 3- (4-phorphenoxy-O-ensyl alcohol and 7.95 g (0.035 mass) 2, 2-dimethyl-3- chloride (2, 2-d :: vinyl chloride) a) -cyclopropanecarboxylic acid is dissolved in 100 ml of anhydrous toluene and 2.8 g (0.035 mol) of pyridine dissolved in 50 ppm of toluene are added dropwise at 2530 ° C. Then the mixture is stirred for another 3 h. The reaction mixture is poured into 150 ml of water, the toluene phase is separated and washed again with water in amounts 100 ml. The organic phase is dried over sodium sulfate and, finally, the toluene is distilled off in a vacuum obtained using a water-jet pump. The last solvent remains are distilled off by initial distillation at a bath temperature (1 Torr). 11 g are obtained (77% of theory) 3 - (4-fluorophenoxy) -benzyl-2,2-dimethyl-3- (2,2dichlorovinylcyclopropanecarboxylate as a yellow oil; n 1,5559. Forms, uses of agents, conventional solutions, emulsions, wettable powders, suspensions, foams, pastes. They are prepared by methods common in the manufacture of preparative forms of pesticides. Tests confirm the biological activity of the proposed compounds, A. Experience with aphids (contact action). Solvent 3 weight.h. acetone; emulsifier 1 weight.h. alkyl aryl polyglycol ether. For the manufacture of a drug of the beginning, 1 weight.h. it is mixed with a solvent containing an emulsifier, and the concentrate is diluted with water to the desired concentration. The preparation of the active principle is sprayed, before the formation of drops, of cabbage plants (Brassica oleracea), which are strongly affected by tobacco aphids (Myzus persicae). After a specified time, the degree of killing is determined. At the same time, 100% means that all the people have died; they are crushed, and 0% means that none have died. The active principle, concentration, duration of determination and results are visible from the table. one:

Active principle

The degree of killing,%, after 1 day

CHj-0-CO-CH-

100 90

OSSN

about SC, -0-CO-CH I Sr2-o-co-vCH c CHj CH3 CHg-O-CO-CH v VBF: CH CHj Ns / g p —r Vk, 0 — CO — CH — f

65048010

Continued table. one

 SNS

B. Experience with a scoop.

Solvent 3 weight.h. acetone; emulsifier 1 weight.h. alkylaryl polyglygol is 35% ether. For the manufacture of the drug active start 1 weight.h. it is mixed with a solvent and an emulsifier and the concentrate is diluted with water to the desired concentration. Prepaid 40 of the current onset of spraying 100

100

80

100

100

95

Cotton leaves are sown up to the moisture content of the dew and plant caterpillars on them (Laphygma exigna). After a specified time, the degree of killing is determined. At the same time, 100% means that all the caterpillars are dead, and 0% is not killed. The active principle, concentration, duration of determination and results are visible from the table. 2. Table 2

Of Mr. O - co - CM - V oCHN

forr vrt: rr / / oswz

CKj SNS

100 80

about

CHj-O-CO-CH-C -Vg: CH

CHj SNS

{ayestno}

100 95, O

CHl-o - with -

CH /

SNS

100 100

about

B. Experience with ticks (stable). Solvent 3 weight.h. acetone; emulsifier 1 wt.h, alkylaryl polyglycol ether. For the purpose of the preparation of the active ingredient, 1 wt.h. it is mixed with a solvent and an emulsifier and the concentrate is diluted with water to the desired concentration. The active drug is sprayed before the drops form. legumes

Vg

CHj-0-CO - CH-V Bg

sns sns

Sc

m, -

0-CO-CH-f

l

SNS SNZ

plants (Phaseolus vulgaris), which are heavily affected by spider mite (Tetranichus urtlcae) in all stages of development. After a specified time, the degree of killing is determined.

The active principle, concentration, duration of determination and the results are visible from the table. 3

Table 3

0.1

100

0.1

100

0.1

98

0.1

sn

100

0.1 /

99

0.1

0.1

98

99

0.1

65048016

15

Sc

snl

o-co-CH-v

w /

CHj SNS

CH /;

0-CO-CH-Vci

sn

g

SNS SNZ

.sk

X

sn

(n - //

X

sa

CHj

SNS

Prolongation {tabl. 3

100

0.1

99

0.1

100

0.1

soci sni Vci

I

hedgehog

Cttj CHj

100

0.1

., - and - UU - that-CH g C

l 1

SKZ SKZ

100

0.1

10D

0.1

sn

sh

SNS

"X 0-CO-vCR" C:

D SNZ Nze CHZ

100

0.1

from

with

11 l O-CO-tgSN C

-r-rUn. i;

BUT

NCS CHS

99

0.1

Sn .01

GO - SK-SM -

X

QSa, CE)

.sn

there is no

vg

X

| GI 0-CO- "K-CH-CH-C

IL J / Bi

100

0.1

99

.0,1

17

0-co-fc

Sn / "MsSize

C1 C1

SNg-0-CO-t CH С

X

CHj SNS

/ С1 о-со-г7 1n: с.

/ V С1 f CHj СНз. Experience with maximum concentration (insects living in the ground are the larvae in the land of Tenebrio molitor). Solvent1 {3 weight.h. acetone; emulsifier 1 weight.h. alkyl aryl polyglycol ether. To prepare the active ingredient, 1 weight is mixed with the solvent, the emulsifier is added and the concentrate is diluted with water to the desired concentration. The active ingredient is mixed thoroughly with the earth. However, the concentration of the active principle in the preparation does not matter, the decisive is the amount of action.

Continued table. 3

100

100

100 100 100

100,100,100 volumes per unit volume of earth, the earth is filled into pots and left to stand at room temperature. After 24 hours, the experimental larvae are planted in the ground and, after further I-7 days, the degree of effectiveness of the active principle is determined by counting the dead and living larvae. The degree of effectiveness is 100% if all the larvae are euthanized, and 0% if the same number of larvae survived as under control. The effect of the beginning, their applied amounts and results are visible from the table. four.

Active principle

SNG, -0-CO-CH

OH CHZ CHS

SNG-0-CO-CH- / VoCH,

CH, /

D. Experience with marginal concentrate, her (living in the land insect larvae of Phorbia anticjua),

Solvent 3 weight.h. acetone; emulsifier 1 weight.h. alkyl arylplylphenol ether For the manufacture of the drug active start 1 weight.h. it is mixed with the indicated amount of solvent, an emulsifier is added and the concentrate is diluted with water to the desired concentration. The preparation of the active principle is thoroughly mixed - with the earth. At the same time, the concentration of the active principle in the preparation plays practically no role, the decisive is the number of active agents.

The degree of killing,%, when the concentration of the current beginning of 2.5 hours, per million

OSSN

go start per volumetric unit of land. The earth is filled into pots and left to stand at room temperature. After 24 hours, the experimental larvae are planted in the cultivated land, and after a further 2–7 days, the degree of effectiveness of the active principle is determined by counting the dead and living larvae. as many larvae remained alive as with untreated controls.

The effective principles, the applied amounts and the results are visible from the table. five.

Table3

SNG-0-CO-CH- /

OSSN

21

Active principles (structure)

65048022

Prolonging Table, 5

The degree of killing,%, when the concentration of the current beginning of 2.5 hours per million

, CN

CH

J 0-soo-cc

l

CHj CH3 -CN

 O-CO-CH-f V-C1

100

100

CH

.Cn

xSng-

o-so-sn- / l sns sns

100

-Snz

CH

CN

 CH

O-CO-CH- -T

F

/

SNS SNZ

/

from fn

o-son with

ASNz

SNS SNZ

sn

Xx

CH O-CO-CH-V-C1 CH

g

/

 SNS SNZ

.Cn

CH

0-СО-СН -) - СНз

/ t

SNS SNZ

sn

And SNZ SNZ

100 CH

100

100

100

100

SNS

CH -O-CO-Qi y-Cl

/

SNS SNZ

100 CH

CHj-O-CO-CH- / V-Br CH

/ cHj SNS

100

E.LDiQQ- (Experimental insects Blatta orlentalis).

The solvent is acetone. 2 vas.ch, the current beginning is absorbed in YuOOobl. solvent. The solution thus obtained is diluted with a further amount of solvent to the desired concentration.

2.5 ml of the active ingredient solution are pipetted into a Petri dish. At the bottom of the Petri dish there is a filter paper with a diameter of approximately 9.5 cm. The cup remains open until all solvent is half.

Cftj snake

, CN

Uj / chj

7h SNS SNz SNZ / CN

s.CH / 7 IJ o-co-f 3 d

will not evaporate (7. Depending on the concentration of the active principle in the solution, the amount of the active principle per 1 m of filter paper varies. Then about 25 experimental insects are planted in the Petri dish and covered with a glass lid. condition of experimental insects. 100% means that all insects are euthanized; 0% none insects are not killed.

The active principle, concentration, experimental insects and results are visible from the table. 6

Table 6

0.02

100

100

0.2

100

0.2

0.2

100

G. (experiment with two-winged insects. Experimental insects - house fly),

The solvent is acetone. 2 p.w., of the active principle absorb in 1000 vol.h of the solvent. The solution thus obtained is diluted with a further amount of solvent to the desired lower concentration. 2.5 ml of the active ingredient solution are pipetted into a Petri dish. A filter paper with a diameter of approximately 9.5 cm is at the bottom of the petri dish. The petri dish remains open until the solvent has completely evaporated.

Syag-O-CO-CH (M

СНз СНз СНг-0-CO-CR-V -OCH,

about)

/ Sc

t / c1

I

CHj SNS

.CHj

CHj CH3 0-CO r-rCH C:

l ci

SNS SNZ

Depending on the concentration of the active principle in the solution, the amount of the active ingredient per 1 m of filter paper is different. Then about 25 experimental insects are planted in a cup and covered with a glass lid. The condition of the insects is constantly monitored. The time required for 100% killing is determined.

The experimental insects, the active principle, the concentration and the time required for a 10 p% killing, are visible from the table. 7

Table 7

0.2

70 6 h 0% 0.02

OSSN

150

0.2 6 h 0% 0.02

30 60 6 h

0.2

80 0.02 6 h

0.2

40 0.02 6 h 70%

thirty

0.2 0.02 100

Gl

55

0.2 0.02 6 h

55

0.2 6 h 60% 0.02

3. Experience with aerosol. (Experimental

insects - room fly O (, usi

resistant to phosphate ester).

Acetone solvent in the amount of 2 cm. For the manufacture of a preparation of the current start, 2 mg is mixed with a solvent. A wire cage is hung in the middle of a gas-tight glass chamber of 1 m in size, in which there is an approximation. Continuation of the table. 7

25 experimental insects. After the chamber is closed again, 2 ml of the active ingredient preparation is sprayed into it. The condition of the insects is constantly monitored externally through the glass walls, and the time required to kill 95% of the insects is determined.

The active principle, the concentration, the time required for 95% killing, are visible from the table. 8. Table &

1930

And, Experience with ticks.

Solvent 35 weight.h. ethylene glycol monomethyl ether, 35 weight.h. nonylphenol polyglycololev ether). 3 parts by weight are mixed for the preparation of the corresponding preparation. current start with 7 weight.h. mixtures of solvent and emulsifier and dilute the thus obtained emulsion concentrate with water to the desired concentration in each case. In these preparations, the active principle is dipped for 1 min before sexual maturity of female ticks of the genus Boophilus microplus - (stable).

After dipping every 10 females of ticks of various genera, they are placed in a Petri dish, at the bottom of which lies a filter disk of the appropriate size. After 10 days, the efficacy of the active ingredient preparation is determined by establishing a delay in the deposition of eggs compared to untreated control mites. Efficiency is expressed in%, and 100% means that they no longer put any eggs, and 0% means that females put a normal amount of eggs.

Effectively acting onset, tested concentrations, underlying;

parasites and the results are visible from the table. 9.

Table 9