SU791199A3 - Acaricidic agent - Google Patents

Abstract

Compounds of the formula I <IMAGE> in which (R)n denotes hydrogen, halogen, nitro, cyano (substd.), alkyl (substd.), alkoxy (substd.), alkylthio (substd.), phenyl (substd.), phenoxy or methylenedioxy and R1 denotes alkyl, alkoxyalkyl, dialkoxyalkyl, dialkylaminoalkyl or cycloalkyl, have insecticidal, acaricidal, fungicidal and/or herbicidal properties, and are obtained by the cyclisation of <IMAGE> with phosgene or carbonic acid esters, and alkaline hydrolysis of the <IMAGE> obtained.

Description

one

This invention relates to chemical plant protection agents, specifically, to an acaricidal agent based on 1-aryl-4-alkyl-1, 2,4-triazol-5-ones derivatives.

A well-known commercial drug is acaricide based on 0,0-dimethyl-S- (2-ethylthioethyl) -thiophosphate (methysystox I).

Also known acaricide, the active ingredient of which is O, 0-dimethyl-5- (benz-1,2,3-dihydrotriazon-4-yl-3-methyl) -dithiophosphate (azanophos-methyl) 2j.

However, these acaricides have insufficient activity at low concentrations.

The purpose of the invention is the search for new acaricidal agents with high acaricidal activity.

This goal is achieved by using as derivatives 1-aryl-4-alkyl-1 / 2,4-triazol-5-ones a compound of the general formula

 .-M K

AND

and

(

R.

in which R is trifluoromethyl, trifluoromethoxy, 1,1,2-trifluoroethoxy, 1,1,2,3,3, 3-hexafluoropropoxy at position 3 or fluorine, chlorine, bromine, iodine, methoxy at position 4; or two chlorine atoms in position 3 and 4;

10 methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl, in an amount of 0.05-90 wt.%.

Compounds of general formula I are obtained by cyclization of a compound of formula

eoOR 1

South NH-K C-NH-K ,, ()

20

where is ri2. alkyl group

the action of phosgene or low molecular weight carbonic acid and the compounds obtained

25

-V w)

 COOR

I

R,

Scalded to the corresponding acids, and the latter decarboxylated.

Transformation II ---- III from -20 to

. The cyclization with phosgene is carried out in the presence of bases and solvents that do not contain protons.

Suitable bases are triethylamine, trimethylamine or pyridine. Benzene, ether, acetone, dioxane, tetrahydrofuran are used as proton-free solvents.

The reactants are fed at very low temperatures and then heated to the reaction temperature. One or both of the reactants are also supplied in whole or in part, and then phosgene is added, and, as necessary, the remaining

part of the reactants at the reaction temperature. The reagents are used in a stoichiometric ratio or with a slight excess of one of the components.

The base required for phosgenation is preferably used in excess with respect to a stoichiometric amount of up to 15%, and phosgene or carbonic ester is used in excess to 20%.

The resulting compound of formula III is precipitated after separation of the salt by filtration by distilling off the solvent. It is washed with an aqueous or aqueous-alcoholic alkali, preferably NaOH, also without removing the solvent, and alkaline salts of (free) acids, which are soluble in the aqueous phase, are first formed. The free acid is isolated by acidification of the aqueous phase and decarboxylated by simple heating, preferably in an organic solvent medium, or by heating the aqueous suspension to 80-150 ° C, preferably 90-120 ° C, or at the boiling point of the solvent or suspending agent used.

The resulting triazoles of formula I are isolated by removal of the solvent (e.g., filtration by suction or distillation) and, if necessary, purified (e.g., by recrystallization).

Amidrazones of the formula II are obtained in a known way, for example, by reacting phenyl diaoneyl salts with ci-haloacetoacetic acid esters and then treating the o-halo-c-phenylhydrazonoglycoxylic acid ester of the formula

, acc. (/ OU)

amines of the formula R. in a known way.

In this way, the following compounds of formula (I) are obtained, which are listed in Table 1.

Table 1

The application forms of the compounds of formula (I) are common: emulsifiable concentrates, wettable powders, solutions.

Example 1. Emulsifying / 1st concentrate is obtained from 15 parts by weight biologically active substances, 75 weight.h. cyclohexane as a solvent, 10 weight.h. ethoxylated nonylphenol and 10 mol of ethylene oxide as an emulsifier.

PRI mme R 2. A wettable powder readily dispersible in water is obtained by mixing 25 parts by weight. biologically active substances, 64 weight.h. quartz containing kaolin, as an inert filler, as well as 10 weight.h. potassium sulfite and 1 weight.h. sodium salt of oleylmethyl taurine as a wetting and dispersing agent, and then crushed in a rod mill.

The following examples illustrate the high activity of the proposed compounds.

2 3 4 5 6

| Continuation of the table, 1 |

Example 3. Strongly affected spider mites, legumes are sprayed with an aqueous suspension concentrate spray to spray,

5 obtained according to Example 2, before dripping, drop by drop. Then sprayed plants are placed in a greenhouse at. Microscopic control is carried out 8 days after

0 spraying. All moving and immobile populations, including eggs, were dead, with compounds of 1,3,4,7,9,12,17,18.

Example 4. Apple trees affected by a stable spider mite (Mefatetranychus uIsni) are treated with an aqueous suspension of the emulsion concentrate prepared according to Example 1 until it is dripped dropwise.

Plants are placed in a greenhouse at 220 ° C and after 8 days they are con- centrated. The results are shown in table 2. table 2

100 95

100 BO 100 100 100 100 100 100 100 100

Methoxistoks I (known)

O, O-dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphate (known)

Methoxistoks I (known)

O, O-dimethyl-S- (N-methylcarbamoylmethyl) -dithiophosphate (known)

Continued table. 2

75

94

Claims (2)

85 Thus, the proposed compounds have a high acaricidal activity at low concentrations. The invention is an acaricidal agent containing an active principle based on derivatives of 1-aryl-4-alkyl-1,2,4-triazol-5-ones and an additive from the group of solid and liquid carriers, so that of acaricidal activity, it contains as a product 1-aryl-4-alkyl-1,2,4-triazol-5-6 but a compound of the general formula R - means or trifluoromethyl, trifluoromethoxy, 1,1,2-trifluoroxy-1, 1 , 1I2,3,3,3-hexafluoropropoxy at position 3; or fluorine, chlorine, bromine, iodine, methoxy at position 4; or two chlorine atoms in position 3 and 4; means methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl ,. the content of the active substance in the medium is 0.05-90 wt.%. Sources of information, ntye taken into account in the examination 1.Shamshurin AD, Krimer MZ Phytochemical properties of pesticides. Chemistry, 1976, p. 88-89. 2. In the same place, from 66-67 (prototype).