SU547170A3 - Insectoacaricidal composition - Google Patents

Description

(54) INSECTIC ACID COMPOSITION

one

This invention relates to insectoacardine formulations based on imidazolines or ethylenediamines.

The derivatives of imidazolines and ethylenediamines are known for controlling insects and glues.

However, their action is not effective when used in small doses.

In order to obtain more effective means, the latter contains the imidazoline or ethylenediamine derivatives of the general formula I

E,

CC1,

where RI and R, which can be odipakovye

or different, is hydrogen, halogen, lower alkyl, alkoxy, or nitro, with the substituents 3, 4 or 5. If the radicals Ri and R are halogen, alkyl or alkoxy, they are generally chlorine or bromine , alkyl or alkoxy groups with 1 to 2 carbon atoms;

RI preferably means a chlorine atom in position 3 or 4 or a methyl group in positonium 3 or 4;

Rj is in particular a hydrogen atom, a chlorine atom or a methyl group.

The active ingredients of the formula I are obtained by reacting the corresponding diaryl-substituted ethylene-amines with chloral by known methods. Hydrogenation 2 is required. The loop closure of imidazolidine with chloral has so far been carried out mainly by using glacial acetic acid or glacial acetic acid and hydrochloric acid as a solvent at room temperature or lightly heated. This method, in the case of 3-mixtures of pl or 3,5-disubstituted dianilinoethanes, does not, however, give any way out or only gives bad results. Therefore, a method has been developed for these compounds in which water is removed in a water-immiscible solvent by azeotropic distillation. For example, benzene, toluene, or xylene was justified, and the addition of a catalyst, such as para-toluene sulphoxyl acid, can accelerate the reaction. This method, also in the case of unsubstituted or substituted diamines, provides pure substances and gives higher yields. The compounds of Formula 1 have a very good action against various pests. Even small dosages of the active ingredient are sufficient to kill, for example, flies (for example, Mussa domestica), cockroaches (for example, Phyllodroma germanica), spider mites (for example, Tetranychus urticae), aphids, for example, Ahia Jabae), caterpillars (for example, Plutella maculipennis) and beetles (for example, Epilachna Vanvestis). Since the insecticoacaricidal action of the agents is related to selectivity, they are excellent for targeted plant protection. For warm-blooded animals, they are virtually non-toxic. It should be emphasized that the active substances, when chloroform is cleaved, quickly decompose into harmless compounds, due to which they do not contaminate the surrounding radium. To control insects, the active ingredients are applied in the usual manner using excipients and fillers, for example, in the form of a concentrated emulsion, suspension, powder, dust, granulate or in a colloidal form. Concentrates, if necessary, are shifted with water, thus obtaining a spray solution, preferably containing 0.02–5 wt. % active ingredient. Cooking examples. Suspended powder, wt. including: 1,3-bms- (4-Tolne) -2-trichloromethylimidazolidin50 Sodium ligninsulfonate 8 Naphthalene sulfate sodium 2 Kaolin20 Siliceous chalk20 The above components are biased and ground using a grinding mill. The particle size is about 2-6 microns. The content of the active substance can be increased in accordance with the reduction of the fillers and it can be approximately up to BO weight. The solution for spraying the desired concentration of the active substance, which is generally U, U2-0%, is prepared by mixing the active substance with water. Dusting agents, wt. including: l, 3-6wc- (3-chlorophenyl; -2-trichloromethylimidazolidin1, 5 Alk98.0 Aluminum alumina stearate 0.5. The active ingredient is ground using a brush mill and mixed with other components. Colloidal form, parts by weight: 1,3-bis- (3-Golil) -: -trichloromethylimidazolidin20, 0 Ethoxylated isotridecanol polyglycol ether (wetting agent, emulsifier) 2, o Ethoxylated polyglycol ether of coconut oil alcohol (wetting agent, emulsifier) 2.5 Alkylphenol pyram glycol 2.5 k-paraffin73,5 These components are pre-dispersed and then milled with a glass bead mill. Grinding is carried out to obtain particles with a size of less than 2 µm, size of 20% of particles is below 1.1 µm. Aerosol, parts by weight: 1,3-bis- (4-Tolyl) -2 -trichloromethylimidazolidin0, 5 Talc35.0 Zinc stearate0.5 Hexadecyl alcohol0.5 Gas-forming substance (freon) 63.5 Suitable as a gas-forming substance, except freon, propane, butane, nitrogen, carbon dioxide or air. Example 1. N, N-6MC - (Z-chlorophenyl) ethylene diamine. 188 g of 1,2-dibromoethane, 383 g of 3-chloroaniline and 300 g of sodium carbonate are stirred at 140 ° C for 5 hours. After cooling to approximately 80 ° C, inorganic substances are dissolved by adding water. The mixture is extracted with ethyl acetate and the organic extract is dissolved in sodium sulfate. The solvent and excess 3-chloroaniline are distilled off in vacuo. The remaining residue can be directly processed, it can also be distilled at 16 mm Hg. Art. and 285 ° C. The crude yield is 215 g (76% of theory). 1,3-bys- (3-chlorophenyl) -2-trichloromethylimidazolidine 112.4 g of M, M-bis- (3-chlorofeyl) ethylene diamine in 500 ml of benzene is heated for 6 hours using a water separator with 100 g of chloral and an additive 10 g paratoluenesulfonic. Then, in vacuum, the mixture is concentrated as much as possible, and the residue is absorbed by heating with 100 ml of ice acetic acid when heated.

acid. After cooling, crystallization begins. The product is filtered off with suction and washed with a small amount of glacial acetic acid and then cooled with methanol. After drying, 115 g (70% of theory) of product are obtained with an mp of 90 ° C.

Pr and measures 2. N, N-6uc- (4-Tolyl) -ethylenendin.

18 g of a 40% glyoxal solution in water are added dropwise to a refluxing solution of 27 g of paratolundine in 225 ml of methanol. During dripping, the Schiff base is released. At the end of the addition, do not heat, stir esh, e for 15 minutes and after cooling aspirate. The residue obtained by filtration is washed with methanol and dried. The product yield with so pl. 168 ° C is 25 g (86% of theory).

i, N-6Mf- (4-Tolyl) -etnlandnamin ..

19 g of Schiff base is hydrogenated in 500 ml of ethanol in the presence of Rene nickel at 10 atm and 60 ° C. After the catalyst is aspirated, the solvent is removed in vacuo and the residue is suspended in petroleum ether, and a white crystalline solid is formed. After suction and drying, the product has a m.p. 94 ° C. The yield is 15.2 g (80% of theory).

1,3-bys- (4-Tolyl) -2 - trpchloromethylimidazolidine.

4.8 g of the hydrogenation product is dissolved in 10 m of glacial acetic acid and a solution of 6.0 g of chloral in 5 ml of glacial acetic acid is added dropwise at room temperature. After a few hours, crystallization begins. After 10-15 hours, the mixture is evacuated and infused with cold methanol. After suctioning out of the mother liquor by adding water, additional precipitate can be obtained. Recrystallization is carried out using mixtures of ethanol or methanol with benzene. T. pl. , yield 5.5 g (74% of theory).

Similarly to the above examples, the compounds of formula 1 indicated in the table can be obtained.

Fort M L a iso b re t s i and

An insecticobacid composition based on ethylenediamine derivatives of imidazolium, a carrier or filler, is due to the fact that, in order to increase the insecticoacaricidal activity,

compound common phoron contains

beginnings

where RI and R, which may be the same or different, are hydrogen, halogen, lower alkyl, alkoxygroup or nitroxy, and the substituents Ri and Rj are in the 3, 4 or 5 position, in an amount of 0.02- 80 wt. % and 99.98-20 wt. % of conventional additives (carrier or filler).

Sources of information taken into account with experts:

1.Chem. Veg. 94, 2839 (1961) (prototype).

2.I. org. Chein. 35, 3140 (1970).