SU694049A3 - Insecticide-acaricide - Google Patents

Description

This invention relates to insect and mite chemical agents, namely to an insecticide-acaricidal agent based on an active principle. A pesticidal agent is known, the active ingredient of which is O 5-dimethyl-L-4-chlorophenylthioamidophosphate 1. A pesticidal agent containing N-methyl-N- (dimethylaminothio) -N - (2-methyl-4-chlorophenyl) formamidine and the usual additives 2 is known. However, its activity is insufficient. The purpose of the invention is to find a new insecticoacaricidal agent based on an active principle, which has an enhanced insecticidal acaricidal effect. This is achieved by using, as an active principle, a compound of the general formula I "1. / / Ie S-N T (01C) 2, chit pho 15 with a st atrium or amine in which R is methyl; R is methyl, methoxy, chlorine, bromine; Rj is methyl, n-butyl, n-octyl, cyclopropyl, or cyclohexyl; R4 is methyl, ethyl, in an amount of 0.1-95 wt.%. Compounds of formula I can be scrubbed by reacting the compounds of the rmula J N CH-N; Hal-S-N: con, () g in the presence of an acid-binding medium. In formulas 1 and III R, - Nd have azane value and Na8 means ohm halogen, especially chlorine and bromine. As acid-binding agents, tertiary yins are used, as well as trialkylamines and pidin, further alkali and alkaline earth metal hydroxides, oxides, carbonates and bicarbonates, as well as alkali metal alcohols, such as potassium t-butylate and sodium methoxide. The method is carried out at a reaction temperature from -20 to + 30 ° C, under normal or elevated pressure, and under known conditions in an inert solvent or diluent or in excess of an acid binding agent used,

Suitable solvents or diluents are, for example, ethers and ether-like compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane and. tetrahydrofuran; amides such as f, N-dialkylated carboxylic acid amides; aliphatic, aromatic, and also halogenated carbon; hydrogen, especially benzene, toluene, xylenes, chloroform, and chlorobenzene; nitriles, such as acetonitrile; dimethyl sulfoxide; and ketones, such as acetone and diethyl ethyl ketone.

Example 1 Preparation of 1- (2-methyl-4-chlorophenyl) -3,5-dimethyl-1,3, 5-triaza-4-sulfa-5-0.0-dimethylphosphoyl-hex-1-ene. f

To a solution of 16.6 g N-methyl-N- (4-chloro-2-methylphenyl) -formamidine, 9.5 g of triethylamine are added with 100 ml of methylene chloride. With constant stirring at about 0 ° C, 18.5 g of a compound of the formula

SNZO I SNZ

P-NСЭО SCl,

then it is stirred for another 30 minutes without cooling, and then 100 ml of water are added. After evaporation of the pre-dried methylene chloride solution under high vacuum, a compound of the formula

SNZ SNZ SNZ

/ 1 I I

C1 - N CH-N-S -Y-G (OCHs) g

about

in the form of a yellow oil with a refractive index of Pro ° 1.5624.

The following compounds are prepared analogously:

SNS

about

II

CH-N-S-N P (OCH3b

I

SNS

20

4 ° 1.5512.

f

N S - (OC gH5) 2;

SNS

 1.5563

SNS about

-N-S-N P (OC2H5) 2)

CHj

4 ° 1.5661

With “h o

 -N-S-N-P (OC2H5) f;

CH5

20.

P; 1.5434.

™ he, about SNT

yN CH-N S-N (OC 2 H 5) g;

SI

CHz-cis

 1.5592 CHjСНзо

/ hLIII

H3-; jHN CH-N-S-N-r (OC2H5) 2J

sn

- CHz-CIS

p 1.5401

sysnz about

1- N CH-N-S-N-P {OC2H5) 2; J

CIS-CIS

oh 5488

en.

SNS

/ -h

lnf yN CH-N-S N

F (oczH5) 2;

V: i / I

CjfHj (U30

 1, 543S

СНзСНзо

, Ik

L / rN CH-N-S-N PIOCzH5) 2

C8Hi7- H)

4 ° 1.5306

SNS

SNZ Oh

/ - (

g- / VN CH-N-S-NR {OC2H5) 2;

CH

NgS CNG CNG

. CH 4 1.5516 N-P (OCzH5) 2 CH NgC. CIS NgC / CH2 1,538 Forms of the use of drugs are common. Example 2, Insecticidal-kiyechnoe action. Cotton plants are sprayed with a 0.05% aqueous emulsion of the active substance obtained from a 10% emulsifiable concentrate. After drying the plaque, each cotton plant is infected with Z, Spodoptera Bittoratis larvae. The test was carried out at 24 ° C and 60% relative humidity. The test results are presented in the table. Example 3. Acaricidal action. On the PhaseoEus vuPgaris plant, 12 days prior to the test for acaricidal action, an infested piece of leaf from the Tetranychus UPticae population is smeared. The transient mobile stages are sprayed from the chromatographic sprayer with emulsified test preparations, so that no flow of the broth for spraying is observed. After 2 and 7 days, the larvae, adults and eggs are visually evaluated on the living and dead individuals and the result is expressed as a percentage. The treated plants are kept in the greenhouse compartments at 25 ° C. The test results are presented in the table.

SNS SNZ

I I

l // - N CH-N-S-N-PtOCH3) 7

 VII

about

3 SNS SNE

 .N CH-N-S-N-P (OCH3) 2

SNE

CHj SNS

I I

/ Bg

 // - N CH-N-S-N-FIOC2H5) 2 SNE SNE SNE

Hj / VN CH-N-S-N-FlOCEH5) z

SNS SNZ

N CH-U-S-N-PiOC2H5) z

SNS

gc / -N CH-N-S-N-P OC2H5) z

BUT

200

100

200

200

200

100

ABOUT

200

200

100

100

200

200 CH3- (/ N-S -NF (OCzHs) g N eH-NS NP (OC2H5) 2 CH2 Nos / h Vg-; j N CH-NSN-PiOC2H5) 2 CitHg (1 hzo CH 3 CH 3 N 3 -NSN- RyUSgNb) 2 CgHj7 (; f СНзо BI-HQbN CH-NSNF (OC2H5) 2 SI CH .;

SNS

SNS

C1H) -N CH-N-S -H (CH3) g (Known)

ABOUT

SNZO in /

P-NH-S-XX yV-ci

CHjS- (Known) Therefore, the proposed insecticide-acaricidal agent has an enhanced insecticidal-acaricidal action ,, 5

Table continuation

800

800

Claims (2)

400 claims Insecto-acaricidal agent containing an active principle and an additive selected from the group of carrier, diluent and filler, characterized in that, in order to enhance the insecticoacaricidal effect, it contains as an active principle a compound of the general formula. 3 CH-N: -RShKchg; in which R) is methyl; Rj is methyl, methoxy, chloro, bromo H, is methyl, n-butyl, n-octyl, cyclopropyl, or cyclohexyl; n is methyl, ethyl, in an amount of 0.1-95 wt.%. Priority in the treatment of m: 30.11.76 with R - methyl, teel, chlorine, bromine, RJ - methyl teat, ethyl; 16.a6.77 when Rj is methoxy, R, is n-butyl, n-octyl, cyclopropyl, cyclohexyl. Sources of information taken into account in the examination 1. Swiss patent 571821, cl. And 01 N 9/36, published. 01/30/76. 2. Laid out for the application of the Federal Republic of Germany 2619304, cl. C 07 C 161/00, published 11/18/76 (prototype).