SU849977A3 - Insectoacaricidic agent - Google Patents

Abstract

Pesticidal phenoxyphenoxy alkyl carbamates with acaricidal, insecticidal and plant growth regulating activity

Description

(54) INSECTIC ACCIDENT

one

This invention relates to means; protection of plants and animals, in particular for the destruction of members of the Akarin family of families with juvenile-hormonal action.

Known means on the basis of N-methylcarbamate General formula

lO-CO-N-CHj fl ..

Oh ss s-

/

,

Jh

R is hydrogen or methyl;

where R and Ra are the same or different, hydrogen, methyl or ethyl, provided that the two radicals of

R, fijj or R simultaneously denote hydrogen;

R is hydrogen, megyl or hydroxymethyl;

However, this tool acts only on adult insects, such as cockroaches, locusts, beetles, etc.

The purpose of the invention is the expansion of the range of insecticoacaricidal agents that act on certain stages of P ..- ZVITIYA insects with higher activity than the known ones.

The goal is achieved by the adoption of insecticaricidal agents, including as an active principle carbamates of the formula

20

and about

Ri

0-CH- (CH,) - CH-0 C-N RI -Ci -CA alkyl, haloethyl or C ,,, is e-alkenyl; R and R - BOflOpOj:;, methyl or R /, is hydrogen or methyl; or RJ and R; (,, 0 together mean the residue CH ,, - CH, -CH, - (n-0.1, 2) in an amount from 0.1 to 95/1, and the rest is auxiliary additives. Physical Constants of the proposed active compounds are presented in Table 1. Compounds of formula I can be used to kill various animal and plant pests, in particular, to kill members of the Akarin range of the ixodide, argazide, tetranichidae, and insect familia acrididae, blattidae, grillidae, and dr. Pesticide action can be significantly extended. As an additive, other organic insecticides and / or acaricides can be added. For example, organic compounds of phosphorus, nitropholes, and their derivatives, formamidines, urea, carbamate, chrysanthemum derivatives, or chlorinated hydrocarbons can be used. Additives can be solid or liquid. and correspond to substances commonly used in the preparation of formulations, for example, natural or regenerated substances, diluents, dispersants, wetting agents, adhesives, thickeners, binder and / or fertilizer. These compounds of the formula I can be processed into piquids, emulsion concentrates, granules, dispersions, aerosol preparations, in solutions or coke. The preparation of the proposed agent is carried out in a known manner by carefully moving and / or grinding the active principles of the formula I with suitable fillers, if necessary with the addition of dispersants or solvents that are inert to the active principles. The active principles can be found or used in solid processing forms, for example, in the form of powdered or chemical preparations for soil application, granulates (coated granules, impregnating grades and homogeneous granules), or in liquid processing formulas. For example, in the form of dispersible in water concentrates of the active ingredient (wettable powders, pastes, emulsions) and solutions. The content of active substances in the described agents is in the range from 0.1 to 95%. To obtain a 5% powdered preparation of the active principle of formula 1, 5 hours of the active principle and 95 hours of talc are used. To obtain a 2% powdered drug, 2 hours of active principle, 1 hour of highly dispersed silicic acid and 97 hours of talcum are needed. To obtain a 5% granulate, 5 h of active ingredient, 0.25 h of epichloropidrine, 0.25 h of cetyl polyglycol ether, 3.50 h of polyethylene glycol and 91 h of kaolin (particle size 0.3-0.8 mm) are used. The active principle is mixed with epichlorohydrin and dissolved in acetone for 6 hours. Polyethylene glycol and cetyl polyglycol ether are then added. The solution thus obtained is sprayed onto kaolin and then the acetone is ground in a vacuum. For the preparation of a 40% wetting powder, 40 hours of active principle, 5 hours of sodium salt of ligninsulphonic acid, 1 hour of sodium salt of dibutipnaphthalenesulphonic acid and 53 hours of silicic acid are used. To obtain a 25% wetting powder, 25 h of the active principle, 1.5 h of a mixture of chalk and hydroxyethyl cellulose (1: 1) are used; 1.5 h of sodium dibutyl naphthalenesulfonate, 19.5 h of silicic acid, 19.5 h of chalk, 28.1 h of kaolin, and 4.5 h of calcium ligninsulfonate. A 25% wettable powder is also obtained by mixing 25 h of the active principle, 2.5 h of isobctylphenoxypolyoxyethylene ethanol, 1.7 h of a mixture of chalk and hydroxyethylcellulose (1: 1), 8.3 h of sodium aluminum silicate, 16.5 h of kieselgur and 46 h of kaolin. 58499 In order to obtain a 10% wettable powder, 10 hours of active principle are used. 3 H of a mixture of sodium salts of saturated sulfates of fatty alcohols, 5 hours of condensation product of naphthalene sulfonic acid with formaldehyde, and 82 hours of kaolin. The active ingredients are thoroughly mixed in suitable mixers with additives and ground in the appropriate mills and rolls. Wettable powders are obtained, which can be diluted with water to obtain a suspension of any desired concentration. A 10% active ingredient, 3.4 hours of epoxidized vegetable oil, 3.4 hours of a combined emulsifier consisting of a polyglycolic ester of fatty alcohol and a calcium salt of alkyl risulphonate, 40 hours of dimethylformamide and 43.2 hours are used to obtain a 10% emulsifying concentrate. xylene. To obtain a 25% emulsifiable concentrate, 25 hours of active principle, 2.5 hours of epoxidized vegetable oil, 10 hours of a mixture of alkylaryl sulfonate and polyglycolic ester of fatty alcohol, 3 hours of dimethylformamide and 57.5 hours of xylene are used. A 50% active ingredient, 4.2 h of tributylphenol polyglycol ether, 5.8 h of calcium dodecylbenzenesulfonate, 20 h of cyclohexanone and 20 h of xylene are used to prepare a 50% wettable powder. From such concentrates, emulsions of any desired concentration can be obtained by diluting them with water. To obtain a 5% drug for spraying, apply 5 h of the active principle, 1 h of epichlorohydrin 94 h of gasoline (boil-off limits of 1601900 s). The same concentration of the drug is obtained by mixing 95 hours of the active principle and 5 hours of epichlorohydrin. Comparative tests for insect-50 acaricidal activity. Listed in table. 2 compounds are subjected, under comparable conditions, to biological tests-methods A, B, and C, which are carried out in the following way. A / Contact action on Tenebrio moUtor 5 7 pupae A certain amount of a 0.1% aqueous solution of a biologically active substance in acetone, corresponding to an amount of a biologically active substance of 10 mg / m, is pipetted into an aluminum pan and evenly distributed. After evaporation of the acetone, 10 freshly-rounded pupae of Tepebrio molitor are placed on the treated surface. The cup is then closed with a mesh claw. After untreated control insects, they leave the shell of the pupae as adults; Experimental insects developed from pupae treated in the described manner are examined in relation to the number of normally developed adults. Grade 5 — Lethal particular extra pupal forms and adult condition (Adultoide), 100% effect; 4 - lethal special forms and non-lethal special forms (adult state); 3 - lethal special forms, non-lethal special forms and normally developing adults; 2 - not lethal special forms and normally developed. adults; 1 - normally developed adults, 0 activity. B / Contact action on the larvae of Dysercus fasck-jtus A certain amount of a 0.1% solution of biologically active matter in acetone, corresponding to the amount of biologically active substance, 10 mg / m, is pipetted into an alumina cup and evenly distributed. After acetone volatilization, 10 larvae of Dysercus fasclatus in the 5th stage of development are placed on the treated surface of the cup, which contains fodder and wet cotton. The cup is then closed with a mesh lid. After about 10 days, i.e. As soon as untreated control insects have passed a full molt to adult individuals, examine the experimental insects developed from the larvae treated in this manner in relation to the number of normal adults. Grade 5 - lethal special forms (death during moulting and extra-larvae) 100% effect; lethal special forms and non-lethal special forms (adult state); lethal special forms; non-lethal special forms; or normal adult individuals; non-lethal special forms and normal adults; normal adult bios, 0% action. C / Effect on Aedes algypti (larvae) Pipette 150 ml of water into a glass into a glass and add such an amount of a 0.1% solution of a biologically active substance in order to obtain its concentrations equal to 10.5 and 1 i.d. After volatilization of the acetone, 30-40 two-day-old Aedes algypti larvae are placed in each of the glasses filled with the biologically active substance. Then the ground feed is added to the cups, then they are closed with a crisp air passing. After 1, 2 and 5 days, possible mortality is determined. Then, attention is paid to the inhibition of pupation, metamorphosis, and molting to adult individuals. Evaluation 1 - mosquitoes at 10 ppm (0% effect) absence of mosquitoes at 10 ppm no mosquitoes at 5 ppm the absence of mosquitoes (100% effective MD .. effect) The basis for these estimates, get the results presented in table. 3. As can be seen from the table. The 3 known compounds are not 100% active against the pests taken for testing, while most of the proposed compounds 1-12 are active in all tests at 100%. 8 Action against grazing mites by Rapicephalus Bursa. 5 adult ticks or 50 tick larvae are counted into a glass tube and immersed for 1-2 minutes in 2 ml of an aqueous emulsion. From the discharge of dilutions containing 100, 10, 1, or 0.1 ppm of the test compound per million. then it is covered with a standard cotton swab and inverted so that the active principle emulsion cannot be soaked with cotton. Evaluation is made in the case of adult organisms after 2 weeks, and in the case of larvae after 2 days. Each experiment was repeated 2 times. Boophilus microplates (larvae) Using a similar series of dilutions, experiments were carried out using 20 sensitive or OP-resistant larvae (stability refers to the tolerance of diazinon). The compounds of formula 1 are effective in this test against adult organisms and the larvae of Rapicephalus bursa and the sensitive or OP-resistant larvae of the Boofilus micropus. Action against Szodopter's IC. li-ttoralis. The laying of Spodoper's littoralis eggs is immersed in a 0.05% acetone solution of the active principle. The treated egg clutch is then kept in plastic bowls at 21 ° C and under conditions of 60% relative humidity. After 3-4 days, the bulging ratio is determined. The compounds of formula I have shown in this test a good action against Spodoper's littoralis eggs. Table 1 CHi-CH-O-C-N HCj, -H5 (CHj, Q -CH,., -CH, -0-.C-N HC, CH.J-0 -CH, j-CH-0-C-N

9849977

Continuation of table 1

ten

Continuation of table 1

CMj, 59-60 -CHd-CH-0-CN HCHd ,, (H) - 5 -CHjt-CH-OGN HC5, H5 61-62 II-CH, 3, KCH, j, 42-43-CH ,,, - 0-CN HC Hg42-43 15 -CH-CH-0-CN HC,;, H5 TII CH, .CH.j O. - (;; Ha-cH, -oc-NH-CH, j 63-64 -9Nb9 g 9 -CH-CH-O-C-MHC "-EC and 5 Q II -CH5, -CH, -CH, j -CH, -0-C-NHCH, 77-79 -CH, g -CH2-0-C-MNH H (iso) 68-69

Table 2 -CKj-CH-0-C-NHC, Hp (H3o) CH „, о nj 1.53 58 -CH, 3, -CH-0-CN ((O I00 -CH2 -CH-0-C- NHCH, j, P 1.5534 -CH., - CH-0-C-NHC ,, H, (iso) 74-75 "OOM 1.5522 -CH i-CH-OC-NHCH-CH ,, j -0-C-NH-CH-CH CH-CHj, -CH, 3, -CH5-0-C-NH-CH5, -CH ,, -C161-63 -SC -SE -CH-0-C- 4 (nj 1.5387 -CH2-CH, -0-C-NH-C HJ (third) 69-70

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0-L G N

nooh oh

9

ten

eleven

12

hg o

sleep

.CHj

0h J

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H (n. O n

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0-

Known NW}

Ctf.Q

Claims (3)

SUMMARY OF THE INVENTION An insecticaricidal agent comprising an active principle and auxiliary additives, characterized in that, in order to increase activity, carbamates of the formula I are used as an active principle where * taken into account during the examination C ^ -C ^ -alkeiyl; hydrogen, methyl or ethyl; hydrogen or methyl; when n = 0, together they mean the residue —CH ₀ —CH ₀ —CH — CH - (p-0, 1,2). in an amount of from 0.1 to 95%, and the rest is auxiliary additives. Rg, ^and or Ro, * 4 and R ^ 1. USSR patent No. 431655, cl. A 01 N 9/24, 1969. 2. French patent No. 2083648 cl. A 3, cl. C> 61 h 13/00, published. 1965 French Patent No. 2086145, 07 C 41/00, published. 1967.