SU650478A3 - Insecticide - Google Patents

Description

(54) INSECTICIDE MEANS

The invention relates to chemical means of protecting plants and animals, specifically to an insecticidal agent based on 2,2-dis) valuable derivatives of 5phenylcarbamoyl-6-hydroxy-; 11-dioxin-4-one.

An insecticide is known, the active ingredient of which is 5-phenylcarbamoyl-6-hydroxy-3-oxin-4-one derivatives.

A closer chemical structure to the proposed compound is an insecticide based on 2,2-dimethyl-5- (4-methoxyphenyl) -carbamoyl-6-hydroxy-L1-dioxin-4-one.

However, these compounds have insufficient activity at low concentrations.

The aim of the invention is to find new insecticidal agents with high insecticidal activity.

To achieve this goal, the use of 2,2-disubstituted 5-phenylcarbamoyl-6-hydroxyldioxin-4-one derivatives of the general formula

he.

7 О о-с-к-к.

A L „

where RI is a phenyl group, once or twice substituted by halogen, methyl, or trifluoromethyl;

R2 is a methyl or ethyl group; Rs is a methyl group or Ra and RS together mean a tetramethylene or pentamethylene group, provided that if R2 and RS each means a methyl group or together a tetramethylene or pentamethylene group, then RI cannot be a 3-chlorophenyl, 4-chlorophenyl, 4-fluorophenyl group or 3,4 dichlorophenyl,

in the amount of 0.5-99 weight. %, preferably 2-40 wt.%.

Under compounds of formula (1) It is necessary to understand both optically isolated, active enantiomers, and mixtures thereof.

The compounds of formula I are obtained by known methods

A. ester of the formula

he

II

Coon.

s

subjected to interaction with aniline of the formula RI-NHa (1P),

B. Compound of Formula

he

0 (IV)

h4-l

Ri

subjected to reaction with an isocyanate of the formula RI-NCO (V).

B. The compound of the indicated formula IV is treated with the compound (acid) of the formula RI-CO-Ng (VI), and in formulas II-VI, Ri-Rs have the meanings indicated for formula I, and R4 represents a Ci-C-alkyl group.

It is preferable to carry out methods A and B in the range of 100-200 ° C, and method B at a reaction temperature lying in the range from O to 200 ° C. Reactions can be carried out at normal or elevated pressure, in the corresponding

The insecticidal action can be significantly enhanced by the addition of other insecticides and / or acaricides.

As additives, for example, organic phosphorus-containing compounds, nitrophenols and their derivatives, formamides, ureas, pyrethrin-type compounds, carbamates and chlorinated hydrocarbons are suitable.

The compounds of formula I can be used alone or with suitable carriers and / or additives. Suitable carrier mi and additives can be liquid or solid substances and correspond to substances used in the preparation of preparations, such as natural and regenerated material inert with respect to the components of the reaction solvent or diluent and, if appropriate, in the presence of a base.

Ether or compounds like ether, amides, aliphatic, aromatic, and also halogenated hydrocarbons, nitriles and ketones are suitable as a solvent or diluent for these reactions.

Tertiary amines can be used as bases, in addition, alkali and alkaline earth metal hydroxides, oxides, carbonates and bicarbonates, as well as alkali metal alkoxides.

Compounds of the general formula

he

o- ,.

p4

(1a)

The compositions are given in table. one

t a b l ii c a 1

agents, solvents, dispersants, wetting agents, finishing agents, thickeners, adhesives and / or fertilizers.

To apply a compound of formula I

can be processed into spray powders, emulsion concentrates, granulates, dispersions, aerosols, solutions or suspensions.

Preparation of the proposed funds

carried out by finely displacing and grinding the compounds of formula 1 with suitable carriers, in an appropriate case, adding dispersants and solvents which are inert with respect to effective substances.

The compounds of formula I can be used in the following formulations. Solid forms: powders for spraying, preparations for spreading into the soil in the form of granules or powders, granules (coated granules, impregnated granulates and homogeneous granules). Liquid form; Efficient hydrate concentrates capable of dispersing in water - wetting powders, pastes and emulsions and solutions. Examples illustrate the high insecticidal activity of the proposed compounds. As a comparative compound, a compound of the formula co-formula is used; a compound of the formula it -co-ain 1D. sy .. ° -sn Example 1. Insecticidal long-term gastrointestinal action. Potato bushes are sprayed with an aqueous emulsion of a biologically active substance (obtained from a 10% emulsifiable concentrate) containing 0.05% of each of the tested compounds. After 8 days, the treated plants are infected with Leptinotarsa decemlineata larvae at the B3-stage. Two plants are applied per compound and the assessment of the killing achieved (killings) is made 2, 4, 8, 24 and 48 hours after infection. The test was carried out at 24 ° C and 60% relative humidity. Results of the effect of the compounds. Compound 100% destruction was achieved in 24 h 0 0% in 24 0% in 48 EXAMPLE 2. Action, inhibition, eating. 2 potato bushes 15 centimeters high and sprayed with 25 ml of acetone-water mixture (1: 1) containing 0.01% of the test substance. After drying, the plants are infected with 10 larvae (per bush) of the species Leptinotarsa decemlineata (L-3-stage). The plants are then covered with a cylinder of sietic material in order to reproduce the possible relocation of the larvae. The cylinder cover is a copper mesh cover. After two days, damage is assessed by eating. Eating at 0.1% of the test substance 1 point. Only traces of eating at 0.1% of the test substance 2 points. Only traces of eating at 0.05% of the test substance 3 points. Only traces of food at 0.01% of the test substance 5 points. Results of the effect of the compounds Compound Example 3. Action against Musca domestica. Every 50 g of freshly prepared nutrient substrate for larvae is suspended in a beaker. Certain amounts of a 1% solution of the corresponding biologically active substance in acetone are pipetted into the beaker, where the nutrient substrate is located, so that the concentration of the biologically active substance in the substrate is 0.1, 0.05 and 0.01%. After stirring the substrate, the acetone is allowed to evaporate for 20 hours. Then 25 one-day larvae for each biologically active substance and each concentration are added to the treated nutrient substrates in the beakers. After the pupae are formed from the larvae, they are separated from the substrate as a suspension in water and placed in containers covered with plastic lids. Calculate the number of water-washed pupae from each glass (the toxicological effect of the biologically active substance on the development of the larva). After 10 days, the number of flies hatched from the pupae is determined. 100% destruction at 0.1 does not reach 1 point.

100% -iroe destruction at 0.1% of the biologically active substance 2 points.

100% eradication 0.05% biologically active substance 3 points.

100% iri destruction 0.01% of biologically active substance 5 points.

Evaluation results

Compound

Score

5 3 5 5 3 3 3 3 5

one

2

3 4

five

6

7

eight

9 10 11 12 А В

but

3

3

2 1

PRI me R 4 Action

against Lucilia ericata.

To 2 ml of plant medium was added 2 ml of an aqueous solution containing 0.1% of the test compound, and then about 30 freshly harvested larvae were placed on this medium. After another 24 hours, the insecticidal effect is determined by determining the degree of killing.

When using compounds 1-5 and 7-9, according to example 1, a 100% killing is achieved.

Thus, the deplored compounds have a high anti-activity at low concentrations.

Claims (1)

Invention Formula An insecticidal agent containing an active principle based on 2,2-disamena, organic derivatives of 5-phenylcarbamoyl-6-oxy-lg-dioxin-4-one, as well as auxiliary components from among liquid and solid carriers, characterized in that insecticidal activity, as a 2,2-disubstituted 5-feiylcarbamonl-6-hydroxy-z-dioxin-4-one derivative it contains a compound of the general formula Jk 0- C - NH A L. where RI is a phenyl group, once or twice substituted by halogen, methyl, or trifluoromethyl; R2 is a methyl or ethyl group; Kz is a methyl group or R2 and Hz together mean a tetramethylene or ientamethylene group, provided that if Rj and RS each means a methyl group or together a tetramethylene or pentamethylene group, then R cannot be a 3-chlorophenyl, 4 chlorophenyl, 4-fluorophenyl or 3.4 dichlorophenyl group moreover, the content of the active substance in the tool is 0.5-99 weight. %