New derivatives of esters of carboxylic acids, method of production thereof, containing insecticides

 

(57) Abstract:

The invention relates to new derivatives of esters of carboxylic acids of General formula I, where R1represents an alkyl group branched or non-branched chain having 1-4 carbon atoms; R2represents a group of formula IV, in which R4represents a hydrogen atom or etinilnoy group; R5and R6are the same or different selected from the group consisting of a hydrogen atom or a methyl group; R7represents a hydrogen atom; R8selected from propargyl, methoxymethyl or methylthio. The method of obtaining derivatives of esters of carboxylic acids of General formula I by reacting carboxylic acids or their reactive derivatives of General formula XII with alcohols or their reactive derivatives of General formula XIII. Insecticides, providing protection from insects, which contain as the active agent derivatives of esters of carboxylic acids of General formula I. 3 C. and 8 C.p. f-crystals, 3 PL.

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HO-R2(XIII)

The scope of the invention

The invention relates to new derivatives of esters of carboxylic acids, sposobiacych inventions

Connection of a number of natural and synthetic pyrethroids are widely used in agriculture and in households, as they possess high insecticidal activity and effect of protection from insects along with their safety to mammals. However, in some areas of their activity are not entirely satisfactory. For example, the necessary insecticides in the form of aerosol sprays for home use, which would contain the active ingredient, which also have the property of quick action and would be lethal effect, but still in practice no pyrethroids characterized at the same time and the specified property, and the respective effect. Therefore, it is still usually use a mixture of pyrethroids with the property performance and strong lethal effect. Further, in the case of some types of insect pests in agriculture, they developed resistance to pyrethroids. Given the above, there is a strong need for new insecticides and agents that protect against insects, which would have been much more useful.

Disclosure of the invention

The present invention was created with the purpose of development is redst protection from insects, i.e. new connections that would have both a speed and a lethal effect, and would be highly safe and excellent from all points of view; development of methods of obtaining these compounds; the provision of insecticides and protection from insects, containing these compounds as active ingredient.

Focusing on research to achieve the above objectives, the inventors have discovered new derivatives of esters of carboxylic acids represented by the following General formula I:

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in which R1represents an alkyl group branched or non-branched chain, containing from 1 to 4 carbon atoms; and

R2represents a group represented by the following General formula IV

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where R4represents a hydrogen atom or etinilnoy group;

R5and R6are the same or different and selected from the group consisting of hydrogen atoms or a methyl group;

R7represents a hydrogen atom;

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio;

and confirmed that these compounds can be found used is in accordance with paragraph 1, of the formula of the invention relates to new derivatives of esters of carboxylic acids, presents General formula I. Although among the esters represented by the General formula I, there are optical or geometric isomers based on spatial patterns of fragments cyclopropanecarbonyl acid and alcohol, all such esters are also included in the scope of the present invention.

Typical examples of new derivatives of esters of carboxylic acids represented by the General formula I are the following; but they should not be construed as limiting the present invention:

(1) Connection 1

5-propargyl-2-furylmethyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1 - propenyl)cyclopropanecarboxylate

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(2) Compound 2

5-propargyl-2-methyl-3-furylmethyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(3) Compound 3

2-methyl-3-propargyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(4) Compound 4

4-propylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(5) Compound 5

2,6-dimethyl-4-propylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(6) Compound 6

4-methoxymethanol 2,2-dimethyl-3-(3-benzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(8) Compound 8

2-methyl-3-propargyl-4-methylidene-2 - cyclopenten-1-yl 2,2-dimethyl-3-(3-ethoxy-3-oxo-1 - propenyl)cyclopropanecarboxylate

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(9) Compound 9

2,6-debtor-4-methylthiomethyl 2. , 2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(10) Compound 10

2-chloro-4,5-methylendioxy--ethenylbenzene 2,2-dimethyl-3- (3-n-butoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(11) Compound 11

5-propargyl-2-furylmethyl 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(12) Compound 12

5-propargyl-2-methyl-3-furylmethyl 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(13) Compound 13

2-methyl-3-propargyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(14) Compound 14

4-propylbenzyl 2,2-dimethyl-3- (3-ethoxy-3-oxo-1-propenyl) cyclopropanecarboxylate

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(15) Compound 15

4-ethoxymethylene 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(16) the Connection 16

2-fluoro-4,5-methylenedioxybenzyl 2,2-dimethyl-3-(3-n-propoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(17) the Connection 17

2 is e 18

2-chloro-5-trifluoromethyl--ethenylbenzene 2,2-dimethyl-3-3 - tert.-butoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(19) Compound 19

5-propargyl-3-furylmethyl 2,2-dimethyl-3- (3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate

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(20) Compound 20

4-methylthio-ethynylbenzene 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl) cyclopropanecarboxylate

In accordance with paragraph 2 claims the present invention relates to new derivatives of esters of carboxylic acids in claim 1, in which the fragment cyclopropanecarbonyl acid has the 1R, CIS-configuration and spatial arrangement of double bonds corresponds to the Z configuration.

Each of the paragraphs 3-5 of the present invention relates to new derivatives of ester carboxylic acid according to claims 1 or 2, which presents any of the following formulas V-XI:

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According to paragraph 6 claims the present invention relates to the stage of implementation of the interaction of carboxylic acids of General formula XII or their reactive derivatives with alcohols of General formula XIII or their reactive derivatives, resulting in getting new derivatives of esters is R>
where R1represents an alkyl group branched or non-branched chain, containing from 1 to 4 carbon atoms.

The General formula XIII has the following form:

HO-R2(XIII)

where R2represents a group of General formula IV

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where R4represents a hydrogen atom or etinilnoy group;

R5and R6are the same or different and selected from the group consisting of hydrogen atoms or a methyl group;

R7represents a hydrogen atom;

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio.

Reactive derivatives of carboxylic acids include, for example, galodamadruga, acid anhydrides, lower alkalemia esters of carboxylic acids, salts of alkali metals or their salts with organic tertiary bases. On the other hand, reactive derivatives of the alcohols include, for example, chlorides, bromides, para-toluensulfonate esters. The reactions are in an appropriate solvent in the presence of reducing agents or organic/inorganic base or acid as a catalyst, if necessary, and, if necessary, under heating.

In ciruits in the presence of dicyclohexylcarbodiimide and 4-dimethylaminopyridine.

If you get esters with preferred spatial structure, usually the most convenient method is a method in which first synthesize carboxylic acid or alcohol with preferred spatial configuration, and then their atrificial; although, there is a way to divide the obtained esters with the use of an agent for the separation of optical isomers. According to paragraph 7 claims the present invention relates to insecticides and means of protection from insects, which contain new derived complex ester of carboxylic acid according to item 1, represented by General formula I:

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where R1represents a branched or unbranched alkyl group containing from 1 to 4 carbon atoms; and

R2represents a group of the following General formula IV

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where R4represents a hydrogen atom or etinilnoy group;

R5and R6are the same or different and selected from the group consisting of hydrogen atoms or a methyl group;

R7represents a hydrogen atom

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio.

The invention according to paragraph 8 refers to insecticides howl acid, in which the fragment cyclopropanecarbonyl acid has the 1R, CIS-configuration and spatial arrangement of double bonds corresponds to the Z configuration.

Each of the paragraphs 9-11 of the claims relates to insecticides and means of protection from insects under paragraph 7 or 8, which contain new derived complex ester of carboxylic acid, which is represented by one formula V with respect to XI.

In accordance with paragraph 1 of the present invention proposed new and useful derivatives of esters of carboxylic acids represented by the General formula I. the Compounds of General formula I are new compounds which are solid or liquid at room temperature and usually dissolve easily in organic solvents.

In accordance with paragraph 2 of the claims of the proposed connections in claim 1, in which the fragment cyclopropane-carboxylic acid has the 1R, CIS-configuration, and the spatial position of double bonds corresponds to the Z configuration.

In accordance with paragraphs 3-5 of the claims proposed particularly useful compounds according to paragraphs 1 or 2.

In accordance with the invention under item 6 proposed effective ASS="ptx2">

In accordance with paragraph 7 of the claims offered useful insecticides and protection from insects, which contain new derivatives of esters of carboxylic acids represented by the General formula I.

When the compounds of the present invention is used on

practice, they can be used without mixing with other ingredients, however, usually they are used in a mixture with a carrier so that it is easier for them to use as insecticides and protection from insects.

Insecticides and protection from insects for use include, for example, emulsifiable concentrates, oil solutions, dusty, dispersible powders in water and aerosols. They can be prepared in accordance with well known methods, according to which the above compounds add an adjuvant such as emulsifiers, dispersing agents, solvents, stabilizers, etc.; solid carriers, liquid carriers; propellants, etc. in accordance with need.

The above connection is also used with wood flour and other appropriate materials-fundamentals, mix to use insecticide or agent protection from insects as a researcher is cstuuyxm organic solvent, which is designed to absorb cloth, or dissolved in an appropriate solvent to be absorbed by the tampon, and then evaporated by heating in an appropriate heating device, that is, when they are used to scare away mosquitoes electricity, they have the same efficiency as in the case of mosquito repellent fumigant.

Insecticides and protection from insects effective against such harmful from the point of view of sanitation, insects like flies, mosquitoes, cockroaches, mites and so on; such insects, pest service, as Tinea translucens, Dermestidae, and so on; against such pests granaries, as Sitophilus zeamais and so on; and moreover, against insect pests, bugs, as Myzus persicae. Aphis gossypii, Nephotettix cincticeps, Delphacidae, Pentatomidae, and so on; against lepidopteran insect pests, as Pieris rapae crucivora, Plutella xylostella, Matestra brassicae, Tortricidae, Carposinidae, and so on; against Coleoptera insect pests, like the scarab beetles, Chrysomelidae, Curculionidae, and so on; Diptera insect pests, as Chironomidae, Agromyzidae, and so on; Orthoptera insects, as Oxya yezoensis. They are also effective against insect pests that are resistant to organophosphorus insecticides and urethane Pesti is aimed (brand MGK-264), a mixture of N-activityconcentration and arylsulfonate (brand MGK-5026), Syhepirine 500, octachlorodipropyl ether, piperonylbutoxide and so on, provides the ability to significantly improve the effectiveness of insecticides and protection from insects according to the invention. In addition, mixtures of other insecticidal or protection from insects ingredients, for example, organophosphorus insecticides, such as fenitrothion, DDVP, diazinon, propafol, predatation and so on, urethane pesticides, such as NAC, RTMS, VRMS, methoxamine and so on, a PYRETHROID insecticides currently used, such as pyrethrin, allethrin, feltrin, permethrin, phenothrin, permethrin, cyphenothrin, etofenprox and so on, organosilicon compounds, as selflove and so on, benzoylacetonate compounds, such as flufenoxuron, chlorfluazuron, and so on , compounds of chloronicotinyl, such as Imidacloprid, acetamiprid and others, compounds of hydrazine as tebufenozide and others, nereistoxin insecticides, such as cartap, thiocyclam, and others, and other ingredients, such as miticide, fungicides, nematicides, herbicides, growth regulators, fertilizers and so on, with insecticide and protection agents against insects of the present invention, oaty and expect a synergistic effect due to these compounds.

In accordance with paragraph 8 of the claims offered more useful insecticides and protection from insects by using as the active ingredient of insecticides and protection from insects of new derivatives of esters of carboxylic acids under item 7, in which the fragment cyclopropanecarbonyl acid has the 1R, CIS - configuration, and the spatial position of double bonds corresponds to the Z configuration.

In accordance with paragraphs 9-11 of the claims offered even more useful insecticides and protection from insects, due to the use of the most useful compounds according to paragraph 7 or 8, as an active ingredient of insecticides and protection from insects.

The following are examples of ways to obtain new derivatives of esters of carboxylic acids of the present invention.

Examples of the synthesis of

An example of obtaining 1.

Synthesis of compound 1. 2.7 g of 5-propargyl-2-furylmethanol alcohol and 2.3 g of triethylamine dissolved in 40 ml of dichloromethane and to the solution was added 4.8 g of floridamedia 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylic acid while cooling the solution with ice. Then the reaction RA is the air traffic management at room temperature for 3 hours, and again washed with 50 ml of saturated brine. After that, the organic layer is dried over magnesium sulfate, the dichloromethane is removed by concentration in vacuo and the resulting oily material is purified on a chromatographic column with silica gel (eluent; ethyl acetate:n-hexane=1:40). The result of 6.1 g of colorless 5-propargyl-2-furylmethyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylate.

IR 3300 cm-1(-CH2-C CH), 1730 cm-1(-COO-)

Example of getting a 2. Synthesis of compound 3 (acid fragment has the 1R, CIS-configuration, and spatial structure corresponds to the Z configuration).

to 4.0 g of 1R, CIS-2,2-dimethyl-3-[1-(Z)-3-methoxy-3-oxopropyl]cyclopropanecarbonyl acid and 3.0 g of (S)-2-methyl-3-propargyl-4-oxo-2-cyclopenten-1-ol dissolved in 50 ml dichloromethane and the resulting solution was added under ice cooling a solution of 4.3 g of dicyclohexylcarbodiimide and 0.2 g of 4-dimethylaminopyridine dissolved in 40 ml of dichloromethane. After stirring for 12 hours at room temperature the solution is filtered, and the filtrate is concentrated by vacuum distillation. The remaining material is purified on a chromatographic column with silica gel (eluent; ethyl acetate:n-hexane = 1: 20). The result is 6.0 g of colorless (S)-2-metric 3300 cm-1(-CH2-CLO), 1730 cm-1(-COO-).

Example of getting a 3. Synthesis of compound 6

4.1 g of 2,2 - dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylic acid are dissolved in 50 ml of acetone and to the solution was added 4.3 g of 4-ethoxymethyleneamino. Then to the solution was added 2.4 g of triethylamine and the reaction continued at 60-80oC for 3 hours under stirring, then add the ether. After the ethereal solution is washed with diluted hydrochloric acid, aqueous sodium bicarbonate solution and brine, it is dried by mirabilite. The ether is distilled off under reduced pressure and obtain 6.3 g of 4-ethoxymethylene 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylate. IR 1740 cm-1(-COO-).

To find out how good insecticides and protection from insects, containing new derivatives of esters of carboxylic acids in accordance with the present invention, provide a number of variants of the present invention and the test results on the effectiveness of the compounds of the present invention are explained below.

Example 1

Yellow kerosene added to 0.2 parts of the compound (1) of the present invention to achieve 100 parts and get 0.2% of MacLane and to 0.8 parts of piperonylbutoxide to achieve 100 parts and get oil solution.

Example 3

10 parts of sarpola SM-200 (trademark of Toho Chemical Industry Co., Ltd. ) and 70 parts of xylene are added to 20 parts of compound (3) of the present invention and with stirring receive a solution. Then get a 20% emulsifiable concentrate.

Example 4

0.4 parts of compound (4) of the present invention and 1.5 parts octachlorodipropyl ether dissolved in 28 parts of purified kerosene and the solution is placed in an aerosol container. Then the container is provided with a valve and through the valve under pressure is injected 70 parts of propellant. Thus receive the aerosol.

Example 5

0.5 parts of the compound (5) of the present invention and 0.5 g BHT uniformly mixed with 99.0 g of the base material for the spiral against mosquitoes, such as pyrethrum, wood flour, starch, etc. and spiral against mosquitoes made well-known manner.

Example 6

0.3 part of the compound (8) of the present invention and 99.7 parts of clay are thoroughly pulverized and mixed, and receive 0.3% dust.

Example 7

40 parts of the compound (10) of the present invention, 35 parts of diatomaceous earth, 20 parts of clay, 3 parts laurylsulphate and 2 parts of carboxymethyl cellulose is shredded and mixed, receiving dispersible in water, p is entrale of the test substances to determine the percentage of immobilized house flies when processing their: 0.2% solution in yellow kerosene compounds of the present invention (A), 0,2% synephrine 500, 0,8% solution in yellow kerosene compounds of the present invention (V), and 0.2% solution in yellow kerosene each of feltrina and phenothrin, then after 24 hours to determine mortality for each of the chemicals. The results are shown in table 1.

Numbers in parentheses indicate the mortality after 24 hours.

From the above test results show that the compounds of the present invention provide an effect of knockdown (performance) exceeding feltrin, which is known to be immobilizing agent, and lethal effect is comparable to or exceeds the effect of phenothrin, which is known to be the murderous agent, and therefore compounds of the present invention is extremely useful as active ingredients of insecticides and protection from insects.

It was also proved that the combination with synephrine 500, which is a traditional PYRETHROID synergist that enhances the insecticidal activity and effect of protection from insects compounds of the present invention.

Example 2 testing the effectiveness of

About 50 adult Culex Pipiens pallens placed in a glass chamber (70 cm3), and then into the chamber p is a spiral, containing compounds(1), (5), (8), (10), (13) and (17), obtained by the method of example 5, ignited and placed in the camera, 80% or more of the Culex Pipiens pallens fall within 30 minutes, and a day later, 80% or more fallen Culex Pipiens pallens are dead.

Similarly, 40 mg of each of the compounds(2), (4), (7), (14) and (19) of the present invention (these compounds were impregnated mats size 2.2 x 3.5 cm) is evaporated by heating on an electric device for mosquito repellent with the temperature of the plate 170oC. the result is a highly effective protection from mosquitoes, the same as in the case of mosquito coils.

Example 3 testing the effectiveness of

Dust containing each of compounds(3), (5), (8), (9), (12) and (16) of the present invention obtained by the method of example 6, evenly applied to the bottom of the Petri dishes with a diameter of 14 cm at a dose of 2 g/m2and on the surface of the walls of the Petri dish put the oil, leaving a net area of 1 cm from the bottom of the Cup. Then 10 adults Prussians in the group are placed freely in a Petri dish so that they could come into contact with dust for 30 minutes, after which they are placed in another container. 3 days later it turns out that 80% or more of the cockroaches die from any of Farrukh Dustov.

Pia (2), (6), (9), (10), (15) and (18) of the present invention obtained by the method of example 3, dilute with water to 1000 times and put in a dose of 100 l/tan (approximately 10.1 l/a) in the field of daikon in stage 5 - 6 leaves infected with Myzus persicae. According to the results of monitoring the degree of survival of parasites 2 days later it was found that the number on each of the fields has been reduced by more than 10 times compared with the number before applying the mortar.

Example 5 testing the effectiveness of

8.0 g of azodicarbonamide, which is an organic blowing agent, and 1.0 g such adjuvant as sintering additive, and so on, added to 1.0 g of each of compounds(1), (3), (9), (11) and (16), after which they are thoroughly mixed and placed in aluminum containers. After the container with this fumigant (which is granulated dust) is heated to approximately 250oC due to the heater in the space of 6 tatami mats, ingredient diffuses throughout the room through the holes made in the container so that the smoke could pass through them. The fumigant was effective not only in the fight against cockroaches, flies and bugs, but also house dust mites, such as Dermato phagoides farinae and Tyrophagus putrescentiae.

The effectiveness of us what moloi (I), are useful compounds, particularly compounds according to paragraph 2, which fragment cyclopropanecarbonyl acid has the 1R, CIS-configuration, and the spatial position of double bonds corresponds to the Z configuration, and the selected specific connection points 3 and 5 have extensive practical application.

In accordance with the method according to item 6, get a new and useful derivatives of esters of carboxylic acids represented by the above General formula I.

Insecticides and protection from insects, containing new derivatives of esters of carboxylic acids according to paragraph 11, which are represented by the above formula (I) possess as property performance and lethal effect in their low toxicity to warm-blooded animals; therefore, they are much more useful than those that contain the currently used pyrethroids. Especially wide practical application are insecticides and protection from insects under item 8, which contain compounds in which the fragment cyclopropanecarbonyl acid has the 1R, CIS-configuration and spatial arrangement of double bonds corresponds to the Z configuration, and protection from the NASA is>/BR>In accordance with example 4 application of 0.2 g of compound (4), compounds (5) or compound (6) according to the present invention, described below, was dissolved in 40 ml of purified kerosene, and filled with a solution of the aerosol container. Then the container was attached to the valve and through it under pressure was introduced 60 ml of propellant (liquefied petroleum gas). Thus gained the aerosol.

The compound (4) according to the present invention

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The compound (5) according to the present invention

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The compound (6) according to the present invention

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30 female adult homemade flies freely placed in a glass chamber with a volume of 60 cm3(0,216 m3), then within 1 second camera was spraying the aerosol. Counted the number of immobilized flies and after 10 minutes of flies was transferred into a plastic container. As food, the flies were given a 3% aqueous solution of sugar. After 24 hours, counted the number of dead flies. The results are shown below in table 2. In table 2 the effect of immobilizing means relative effectiveness of the test compound compared with the accepted for 1,00 activity feltrina commonly used as an immobilizing agent, and lethal effect means the ratio smart the
Comparative compound a

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(Optical configuration of acid fragment: 1R-CIS-Z)

Comparative connection

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(Optical configuration of acid fragment: IR-CIS-Z)

2. The RESULTS are shown in table. 2.

3. DISCUSSION

Previously known aerosols shared feltrin, known as the immobilizing agent, and killing agents, such as phenothrin or resmethrin. The test results prove that the compounds of the present invention without regard to the optical configuration of their acid fragment have an immobilizing effect, superior to comparative connections with optical configuration, which gives a relatively high activity, and lethal effect far beyond feltrin or comparative compounds. Thus, all these compounds have the effect of immobilizing agent, and the effect of killing agent, even if they apply without additives, and because they are extremely useful as an active ingredient of insecticides.

TEST 2

Test method and used in the test compounds according to the invention completely repeat these Tests 1.

As sravnitelnyye acid fragment: 1R-CIS, trance)

COMPARATIVE CONNECTION

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(Optical configuration of acid fragment: 1R-TRANS)

COMPARATIVE CONNECTION WITH

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(Optical configuration of acid fragment: 1R-TRANS)

COMPARATIVE COMPOUND D

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COMPARATIVE COMPOUND E

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(Optical configuration of acid fragment: 1R-CIS, TRANS)

COMPARATIVE COMPOUND F

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(Optical configuration of acid fragment: 1RS-CIS-Z)

6. The RESULTS are shown in table. 3.

7. DISCUSSION

The test results prove that the compounds of the present invention without regard to the optical configuration of their acid fragment have an immobilizing effect, superior to comparative connections with optical configuration, which gives a relatively high activity, and lethal effect far beyond feltrin or comparative compounds. Thus, all these compounds have the effect of immobilizing agent, and the effect of killing agent may be greater than previously known, even if they apply without additives, and because they are extremely useful as an active ingredient of insecticides.

CHARACTERISTIC PIR>-1< / BR>
Connection (4) 3250 cm-1, 2100 cm-1(-C=CH)

The compound (5) 3250 cm-1, 2100 cm-1(-CH2-C=CH)

Compound (7) 3250 cm-1, 2150 cm-1(-C=CH)

Compound (8) 3300 cm-1(-C=CH), 1720 cm-1(-COO-),

Connection (9) 2950 cm-1, (-S-CH3), 1730 cm-1(-COO-), 1250 cm-1< / BR>
The compound (10) 3250 cm-1, (-C=CH), 1270 cm-1, 1050 cm-1< / BR>
The compound (11) 3200 cm-1, (-C=CH)

The compound (12) 3300 cm-1, (-C=CH)

The compound (13) 3300 cm-1, (-C=CH), 1720 cm-1(-COO-),

The compound (14) 3300 cm-1, (-C=CH)

Connection (15) 1100 cm-1, (-CH2-O-CH3)

Compound (16) 3250 cm-1, (-C=CH), 1250 cm-1, 1050 cm-1< / BR>
The compound (17) 2950 cm-1, (-S-CH3), 1740 cm-1(-COO-), 1050 cm-1< / BR>
The compound (18) 3250 cm-1(-C=CH), 1010 cm-1< / BR>
The compound (19) 3310 cm-1(-CH2-C=CH), 3150 cm-1(-C=CH)

The compound (20) 3200 cm-1(-CCH), 2950 cm-1(-S-CH3)(

1. Derivatives of esters of carboxylic acids represented by the General formula I

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in which R1represents an alkyl group branched or non-branched chain having from 1 to 4 carbon atoms;

R2is g the B> and R6are the same or different and selected from the group consisting of a hydrogen atom or a methyl group;

R7represents a hydrogen atom;

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio.

2. Derivatives of esters of carboxylic acids under item 1, in which the fragment cyclopropanecarbonyl acid has the 1R-CIS-configuration, and the spatial position of the double bond, the Z-configuration.

3. Derived complex ester of carboxylic acid under item 1 or 2, having the formula VIII

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4. Derived complex ester of carboxylic acid under item 1 or 2, having the formula IX

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5. Derived complex ester of carboxylic acid under item 1 or 2, having the formula X

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6. The method of obtaining derivatives of esters of carboxylic acids represented by the General formula I

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where R1represents an alkyl group branched or non-branched chain having from 1 to 4 carbon atoms;

R2represents a group of General formula IV

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where R4represents a hydrogen atom or etinilnoy group;

R5and R6are the same or different and selected from the group RAS from the group consisting of groups of propargyl, methoxymethyl or methylthio,

in which carboxylic acids or their reactive derivatives represented by General formula XII

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where R1represents an alkyl group branched or non-branched chain having from 1 to 4 carbon atoms;

and alcohols or reactive derivatives represented by the General formula XIII

HO-R2,

where R2represented by the General formula IV

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in which R4represents a hydrogen atom or etinilnoy group;

R5and R6are the same or different and selected from the group consisting of a hydrogen atom or a methyl group;

R7represents a hydrogen atom;

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio,

subjected to interaction with each other.

7. Insecticides that contain as active agent derivatives of esters of carboxylic acids represented by the General formula I

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in which R1represents an alkyl group branched or non-branched chain having from 1 to 4 carbon atoms;

R2represents a group of General formatsa the same or different and selected from the group consisting of a hydrogen atom or a methyl group;

R7represents a hydrogen atom;

R8selected from the group consisting of groups propargyl, methoxymethyl or methylthio.

8. Insecticides on p. 7, which contain the connection in which the fragment cyclopropanecarbonyl acid has the 1R, CIS-configuration, and the spatial position of the double bond, the Z-configuration.

9. Insecticides on p. 7 or 8, which contain the compound represented by formula VIII

< / BR>
10. Insecticides on p. 7 or 8, which contain the compound represented by formula IX

< / BR>
11. Insecticides on p. 7 or 8, which contain the compound represented by the formula X

and

 

Same patents:

The invention relates to protective means for tissues, in particular clothing, carpets and other products

The invention relates to chemical agents contact action for the destruction of household insects ceratapion (moths and koreeda)

The invention relates to pyrotechnic insecticidal compositions and can be used to kill harmful insects: flies, mosquitoes, block, bugs, etc

The invention relates to compositions based on synthetic pyrethroids, which can be used to deal with household insects, such as insecticide chalks

Acaricide // 2280983

FIELD: agriculture.

SUBSTANCE: invention relates to acaricidal agent containing (mass %): alpha-cypermetrin 0.15-0.25; imiprotrin 0.10-0.35; N-octylbicycloheptadicarboximide 0.8-1.2; triethylene glycol 1.0-2.0; solvent 43.0-50.0; and balance: hydrocarbon propellant.

EFFECT: acaricide of increased effectiveness against red ticks (Rhipiceplalus everti).

2 cl, 4 tbl

FIELD: chemistry.

SUBSTANCE: present invention relates to (5-benzyl-3-furyl)methyl 2,2-dimethyl-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate with formula 1:

EFFECT: high pesticide activity.

5 cl, 1 tbl, 16 ex

FIELD: agrochemistry.

SUBSTANCE: invention provides a stable aqueous formulation of hydrophobic pesticide by emulsifying aqueous phase and a water-immiscible phase, the former containing poly(alkylene glycol) ether and the latter hydrophobic pesticide and one or several emulsifiers selected from group including carboxylate, sulfate, sulfonate, alcohol solutions of ethoxylated and alkylphenolethoxylate, fatty acid ethyl ester, sorbitol ester, ethoxylated fat or oil, aminoethoxylate, ethylene oxide/propylene oxide copolymer, fluorocarbon, and siliceous polymer.

EFFECT: increased stability of formulations.

38 cl, 1 tbl, 12 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention relates to novel 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl-2,2-dimethyl-3-(2-cyano-3-hydrocarbyloxy-3-oxo-1-propenyl)cyclopropane carboxylates of the formula (1): wherein G means (C1-C4)-alkyl or (C3-C4)-alkenyl, and to a composition used for control of pest-insects comprising the effective amount of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl-2,2-dimethyl-3-(2-cyano-3-hydrocarbyloxy-3-oxo-1-propenyl)cyclopropane carboxylate of the formula (1). Also, invention relates to a method for control of pest-insects involving applying the effective amount of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl-2,2-dimethyl-3-(2-cyano-3-hydrocarbyloxy-3-oxo-1-propenyl)cyclopropane carboxylate of the formula (1) on pest-insects or in their residence medium.

EFFECT: valuable properties of compounds.

5 cl, 1 tbl, 22 ex

FIELD: agriculture, veterinary science.

SUBSTANCE: composition contains alphametrin, surface-active agent, alcohol, solvent chloracetophos, glycerine and dimethylsulfoxide; isopropyl alcohol - as alcohol, neonol - as surface-active agent, in the following ratio of components, wt %: alphametrin 5-10, chloracetophos 5-10, neonol AF 9-10, isopropyl alcohol 10-15, dimethylsulfoxide 3-6, glycerine 3-6, solvent remaining part. The composition contains propylene glycol and mixed benzine-oil solvent for rubber-processing industry with final boiling point of 80-120°C or mixed benzine-oil solvent with final boiling point of 50-170°C taken in the weight proportions equal to 1:(7-8) as a solvent.

EFFECT: increasing the composition efficiency.

3 tbl

FIELD: agriculture.

SUBSTANCE: substances are described to fight insects, which contain thiacloprid and one of further listed compounds in the ratio that provides for synergism effect: acrinatrin, alpha-cypermethrin, betaciflutrin, cyhalothrin, cypermethrin, deltametrin, lambda-cyhalothrin, permethrin, zeta-cypermethrin, ciflutrin, biphenthrin, gamma-cyhalothrin.

EFFECT: agents have very good insecticide properties.

1 cl, 8 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an ester compound of formula , which can be used in pest control. In formula (1), R denotes a C1-C4 alkyl group or a C3-C4 alkenyl group and A denotes a single bond or an oxygen atom. The invention also relates to a pest control agent, a pest control method and use of the compound of formula (1) for pest control.

EFFECT: use of the compound of formula (1) for pest control.

6 cl, 2 tbl, 19 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an ester compound of formula (I) which can be used in pest control.

EFFECT: invention also relates to a composition containing a compound of formula (I), a pest control method and use of the compound of formula (I) in pest control.

5 cl, 1 tbl, 14 ex

FIELD: chemistry.

SUBSTANCE: invention relates to anti-insecticidal preparations. Aerosol composition contains oil-soluble insecticidal component (A), hydrophobic organic solvent (B), water (C), non-ionogenic surface active substance (D) and propellant (E). Oil-soluble component (A) represents 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl-3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropane carboxylate. Non-ionogenic surface active substance (D) has HLB in the range from 4.1 to 7.0.

EFFECT: invention makes it possible to increase insecticidal activity of preparation.

6 cl, 2 ex, 2 tbl

FIELD: agriculture.

SUBSTANCE: invention relates to insecticides. Insecticidal composition comprises volatile pyrethroid insecticide characterised by a vapor pressure at 20C greater than 9.010-6 hPa, a solvent-soluble polymer, and a solvent. The coating of insecticidal composition is applied on the surface, and evaporation of the solvent is ensured.

EFFECT: invention enables to release insecticides without necessity of additional energy input.

11 cl, 1 dwg, 1 tbl, 5 ex

FIELD: chemistry.

SUBSTANCE: dosage unit in form of pressed tablet for delayed release of insecticide contained evaporating insecticidal preparation and solid inert base. Solid base contains two-component system, which includes material for giving volume and material, providing porosity. Material for giving volume is selected from group of filling agents of direct pressing. Porosity-providing material is represented by carbonate or bicarbonate. Device of insecticide supply contains capacity for insecticide. To obtain dosage unit ingredients are mixed and tablets are formed at temperature which is higher than temperature of insecticide melting. Insecticide measuring apparatus contains dosage unit as single source of insecticide. Composition is in form of tablet, placed near heater. Device contains fork, providing electric connection with heater, and cap for tablet, containing casing and cover.

EFFECT: elaboration of tablet for delayed release of insecticide.

13 cl, 2 dwg, 1 ex

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