Dialkylamide derivatives of pyrethroid acids eliciting insecticide and acaricide activity

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes dialkylamide derivatives of pyrethroid acids of the general formula (III): wherein R1 and R2 represent organic radicals and each radical represents ethyl, or they both can be bound and in common with nitrogen atom represent piperidide, hexamethyleneimide, morpholide. Represented compounds are used as chemical agents for control of insect-pests in agriculture, veterinary science and cattle breeding.

EFFECT: valuable properties of compounds.

2 dwg, 4 ex

 

The invention relates to chemistry and organic chemistry, namely the creation of highly effective insecticides and acaricides, which can be used as chemical weed control insect pests in agriculture, veterinary science, animal husbandry, household and so on

One of the most successful solutions in this area pyrethroids are synthetic analogues of natural pyrethrins. Synthetic pyrethroids - permethrin, cypermethrin, deltamethrin (decis), fenvalerate, cigalotrin, cyfluthrin, fenpropathrin and others are highly effective in low concentrations and relatively low toxicity to humans and warm-blooded animals [1, 2].

Most of these compounds are esters of any of a PYRETHROID acid and 3-phenoxybenzyl or alpha-cyano-3-phenoxybenzyl alcohol or their fluorinated analogues of General formula (I):

Here the fragment RCO - (shown dotted) is the acyl residue of any PYRETHROID acids;

X=H or CN;

Y=H or F.

While in the development of new analogues of pyrethroids varying organic radical RCO (remainder of a PYRETHROID acid) is conducted in various areas, as an alcohol component are typically used, as a rule, traditional is Molekulyarnye blocks, containing residues of 3-phenoxybenzyl alcohol (permethrin, phenothrin), alpha-cyano-3-phenoxybenzyl alcohol (cypermethrin, cigalotrin, deltamethrin, fenvalerate, fenpropathrin and others) or their fluorinated analogues (cyfluthrin, flumethrin). They are all esters have the General formula:

Here RCO is the acyl residue of a PYRETHROID acid;

X=H or CN; Y=H or F.

Thus, diphenyloxides molecular unit explicitly present in the alcohol part of the molecules of these compounds. Developed individual pyrethroids, which also contain diphenyloxide block, but are not esters (etofenprox). PYRETHROID, bifenthrin is a complex ether, but instead diphenyloxide block it has in many respects it is similar to the rest of the biphenyl [3].

The disadvantage of these compounds is that diphenyloxide fragment itself is chemically very stable and difficult to biodegrade, and some conditions also have the potential to be a source of highly toxic polychlor-dibenzodioxins or almost as dangerous polychlor-dibenzofurans.

Thus, from an environmental point of view, most of the existing pyrethroids can be considered potentially dangerous. Cyanide pyrethroids are also some ek is a logical threat, as their industrial synthesis necessarily involves the application of highly toxic salts of hydrocyanic acid.

Also known pyrethroids, in which the alcohol part represents the balance of polyfluorinated benzyl alcohol (tefluthrin, transfluthrin and others):

Here RCO is the remainder of a PYRETHROID acid;

X=H or CN,

Y=H, CH3or F.

However polyfermenticus alcohols are still not readily available and the cost is relatively expensive. Because polyfluorinated organic compounds of different chemical inertness, these substances cannot be fully biodegradable after its main function. Therefore, even when its comparative safety of the use of such pyrethroids will lead to accumulation of these substances in the environment.

The present invention is the development of high-performance insectoacaricidal new type, characterized by accessibility, ease of synthesis and environmental safety.

This object is achieved by the creation of a new class of pyrethroids, in its chemical structure representing acylated PYRETHROID acids derivatives of aliphatic or alicyclic secondary amines such as diethylamine, piperidine, hexamethylenimine, research, etc:

where RCO is the acyl residue of a PYRETHROID acid.

The invention

Dialkylamino derivatives permetrina acid of General formula III:

where RCO is the acyl residue permetrina acid, R1and R2- organic radicals, each represents ethyl or can be chemically linked together with the nitrogen atom represent piperita, hexamethylenimine morpholin exhibiting insecticidal and acaricidal activity.

To illustrate the invention the following are specific examples of carrying out the invention in example 4 dialkylamide derivatives of 3-(2,2-dichlorovinyl)-2,2-dimethyl-cyclopropanecarbonyl (permetrina ) acid belonging to a new class of pyrethroids.

Figure 1 depicts the 4 new compounds are derivatives permetrina acids and secondary amines, which formulas are built in accordance with our principle.

The dashed rectangle shows the remains of permetrina acid, i.e. fragments in common with traditional ester pyrethroids based permetrina acid (permethrin, cypermethrin, cyfluthrin, and others)

Fig. 2 shows 2 possible schemes synthesis of the pyrethroids dialkylamino type on the example of piperidine 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (permetrina) acid. The first scheme, as well as in the industrial synthesis of cypermethrin, uses the acid chloride permetrina acid. The second scheme comes directly from permetrina acid, without transforming it into the acid chloride. Due to the lack of end connection of the cyano groups both schemes synthesis eliminate the use of cyanide salts.

Examples of specific syntheses.

In accordance with our principles, we have synthesized 4 new connections, representing dialkylamino derivatives permetrina acid. For synthesis were used technical acid chloride cypermethrine acid production Indian agrochemical company Meghmani Organics Ltd. and secondary amines - diethylamine, piperidine, hexamethylenimine and morpholine in the form of free bases. In all 4 cases, the General scheme of the synthesis is as follows:

Example 1. Synthesis of diethylamide cypermethrine acid.

In the beaker was measured about 19 ml (˜0.1 mol) of a technical carboxylic cypermethrine acid (DV acid chloride, Meghmani Organics Ltd.) and poured it into a flat-bottomed flask. The beaker and the funnel was washed with 30 ml of tetrahydrofuran (THF) and added it to the same flask.

Then portions added to the mixture a solution of 22 ml (˜0.2 mol) of diethylamine in 20 ml of THF. The reaction of the prot is Ala very rapidly, and the solution appeared white flakes. The flask was periodically cooled by lowering it into cold water. Upon completion of addition of solution to the beaker and the funnel was washed with 50 ml of hot THF, was added to the flask, mixed and covered the reaction mixture with a rubber stopper. After 12 hours turbid viscous solution was filtered, the filter is then treated with hydrochloric acid diethylamine again washed with 20 ml of hot THF and filtered it in the same flask.

Formed pale yellow solution, which contains about 26.4 g (0.1 mol) of diethylamide cypermethrine (permetrina) acid. The output of the substances close to quantitative.

About 10 ml of this solution was poured into a test tube and was heated on a water bath to stop the boil (this Argonauts THF, BP. 66°). Then added about 20 ml of water, with diethylamid cypermethrine acid settles to the bottom in the form of a yellow oily liquid that is not miscible with water. The tube was boiled for 10 minutes, then put in the freezer. At a temperature of approximately 0°diethylamid cypermethrine acid solidifies in white prapinabracni crystalline mass.

Example 2. Synthesis of piperidine cypermethrine acid.

In the beaker was measured about 21 ml (˜0.1 mol) of a technical carboxylic cypermethrine acid (DV acid chloride, Meghmani Organics Ltd.) and poured through a funnel into a flat-bottomed to the BU. The beaker and the funnel was washed with 33 ml of THF and added it to the same flask.

Then portions added to the mixture a solution of 24 ml (˜0.2 mol) of piperidine in 26 ml of THF. The reaction proceeded very rapidly, and the solution appeared white flakes. In the intervals with stirring, the flask was cooled by lowering it into cold water. Upon completion of addition of solution to the beaker and the funnel was washed with 52 ml of hot THF, was added to the flask, mixed and covered the reaction mixture with a rubber stopper.

After 12 hours turbid viscous solution was filtered, the filter is then treated with piperidine hydrochloric acid, again washed with hot THF (2 x 20 ml) and filtered it in the same flask. Formed a yellow-orange solution, which contains about 27.6 g (0.1 mol) of piperidine cypermethrine (permetrina) acid. The output is close to quantitative.

About 10 ml of this solution is poured into a test tube and boiled in a water bath to remove THF, the remaining yellow oily liquid was added about 30 ml of water, brought to a boil, then cooled. The product is not miscible with water. Upon cooling, piperidin cypermethrine acid gradually zakristallizuetsya in white prapinabracni, crystalline mass.

Example 3. Synthesis of hexamethylenimine cypermethrine acid.

In the beaker was measured about 22 ml (˜0.1 mol) of technical acid chloride of cypermethrine the th acid (DV acid chloride, Meghmani Organics Ltd.) and poured through a funnel into a flat-bottomed flask. The beaker and the funnel was washed 29 ml of THF and added it to the same flask. Then portions added to the mixture solution, 28 ml (˜0.2 mol) of hexamethylenimine in 24 ml of THF. The reaction proceeded very rapidly, and the solution appeared white flakes of hydrochloric acid hexamethylenimine. In the intervals with stirring, the flask was cooled by lowering it into cold water. Upon completion of addition of solution to the beaker and the funnel was washed with 20 ml of hot THF, was added to the flask, mixed, covered the reaction mixture was capped and left for the day.

After 12 hours turbid viscous solution was filtered, the filter is then treated with hydrochloric acid of hexamethylenimine again washed 2 times with warm THF (21+24 ml), pressed and filtered in the same flask. Formed yellow solution, which contains about 29 g (0.1 mol) of hexamethylenimine cypermethrine (permetrina) acid. The output is close to quantitative.

About 10 ml of this solution is poured into a test tube and boiled in a water bath to remove THF, the remaining liquid is added about 30 ml of water, brought to a boil, then cooled. This yellow product resembling molten wax, settles to the bottom of the tube. Hexamethylenimine cypermethrine acid - yellow, viscous liquid, heavier than water, with the consistency of honey, TPL about 0°C.

Example 4. Syndesmotic cypermethrine acid.

In the beaker was measured about 20 ml (˜0.1 mol) of a technical carboxylic cypermethrine acid (DV acid chloride, Meghmani Organics Ltd.) and poured through a funnel into a flat-bottomed flask. The beaker and the funnel was washed 29 ml of THF and added it to the same flask. Then portions added to the mixture a solution of 22 ml (˜0.2 mol) of the research in 30 ml of THF. The reaction proceeded very rapidly, and the solution appeared abundant white precipitate hydrochloric acid of the research. In the intervals with stirring, the flask was cooled by lowering it into cold water. Upon completion of addition of the solution, the beaker and the funnel was washed with 30 ml of hot THF, was added to the flask, mixed, covered the reaction mixture was capped and left for the day.

After 12 hours turbid viscous solution was filtered, the filter is then treated with hydrochloric acid the research again washed 2 times with hot THF (24+24 ml), pressed and filtered in the same flask. Formed colorless, slightly greenish solution, which contains about 28 g (0.1 mol) of morpholine cypermethrine (permetrina) acid. The output is close to quantitative.

About 10 ml of this solution is poured into a test tube and boiled in a water bath to remove THF, the remaining liquid is added about 30 ml of water, brought to a boil, then cooled. This yellow product resembling molten wax, settles to the bottom of the tube. Morpholin cypermethrine sour the s - yellow viscous liquid heavier than water, with the consistency of honey, TPL about 0°C.

All the synthesized compounds are a new class of PYRETHROID insectoacaricidal dialkylamino type. This design implementation, as a replacement for alcohol residues in the pyrethroids on the remnants of secondary amines (such as diethylamine, piperidine, hexamethylenimine and others), provides the following benefits :

Secondary amines, such as diethylamine, piperidine, hexamethylenimine, morpholine, are available and large-tonnage chemical products, and their price is considerably lower than the cost of derivatives of 3-phenoxybenzyl alcohol, 3-phenoxybenzaldehyde and other similar compounds commonly used in the synthesis of PYRETHROID ester type. In addition, the remains of secondary amines (diethylamine, piperidine, hexamethylenimine, research and others) easily subject to biological decay and do not accumulate in the environment.

Many famous pyrethroids contain alcohol part of the alpha-cyano, and their industrial synthesis requires the use of highly toxic cyanide. Replacement residual alcohol remains on the secondary amines can completely abandon the use of cyanide in the synthesis.

Because amines allroots much easier alcohols, to obtain Pietr the Idov dialkylamino type intermediate stage of the synthesis of the acid chloride of a PYRETHROID acid can in some cases eliminate, and used for acylation of amines itself a PYRETHROID acid, without prior conversion to the acid chloride.

The proposed connection we have developed a new class of pyrethroids dialkylamino type, also have a high repellent activity against insects, as they are the analogues of such compounds, as cypermethrin, fenvalerate, fenpropathrin and others, but also many well-known repellents - N-acylated derivatives of diethylamine, piperidine, hexamethylenimine and other secondary amines. Due to the fact that in the invention as components, alleluya the residue of a secondary amine, is used the rest of it is a PYRETHROID acid, we have developed a new class of compounds combines the advantages of both known industrial pyrethroids and proven repellents dialkylamino type, such as diethyltoluamide (DETA), N-benzoylpiperidine, oximat and other

- The fact that, as the acid component compounds offered by us are used to the traditional "PYRETHROID acids, will help to organize the implementation of the invention on the same plants that are currently producing conventional PYRETHROID ester type. Thus, the invention seamlessly blends Vuze existing industrial process.

- Introduction of our invention will in the end make a PYRETHROID insecticides cheaper, affordable and environmentally safe, and their use in agriculture (for example, to control insect pests) can provide significant economic benefits.

Preliminary tests of individual representatives of a new class of compounds in the field, conducted in June-August 2004 (Kayakent, southern Dagestan) showed high insecticidal and acaricidal activity of a new class of pyrethroids dialkylamino type against a number of pests of agriculture, and the activity is not inferior, and in some cases slightly exceeded that of these the most widely used industrial pyrethroids like cypermethrin and cigalotrin.

The test drugs, provisionally designated as Pyr-I, Pyr-II, Pyr-III represent a 25% solution of tetrahydrofuran-3 derivatives permetrina (cypermethrin) acid.

For testing 15 g of the drug (25% solution of the active substance [DV] tetrahydrofuran [THF]) was diluted in 10 l of water while stirring, and the resulting emulsion was carried out spraying plots (10 liters per hundred square meters). Similarly conducted and test experience, which as LW was used industrial PYRETHROID cypermethrin company Meghmani Organics (Gah adabag, India). Treatment was carried out hand sprayer at a pre-populated identified the clusters leafroller moth on the grapes.

In these conditions, all three compounds (Pyr-I, Pyr-II, Pyr-III) showed high insecticidal activity against the larvae of moth leafrollers.

References

1. Erie. Natural plant protection from pests, trans. from eng. M.: Mir, 1986.

2. John Leahey. The Pyrethroid Insecticides, 1985, Taylor and Francis, London.

3. Insecticide fact Sheet. Journal of Pesticide reform/SUMMER 1998 - Vol.18, No 2141.

Dialkylamino derivatives permetrina acid of General formula III

where RCO is the acyl residue permetrina acid, R1and R2- organic radicals, each represents ethyl or can be chemically linked together with the nitrogen atom represent piperidyl, hexamethylenimine, morpholin exhibiting insecticidal and acaricidal activity.



 

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The invention relates to organic chemistry, specifically to new chemical compounds- polyfluoroankyl-nitroanilines and their N-ACI-derivatives of the General formula 1

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where (a) RF=CF3; C2F5; C3F7; C4F9; C6F13; H(CF2CF2)nwhere n=1,2,3;

R=H, alkyl (C1-C4Ph;

R1=H; C(O)R3where R3=H, alkyl (C1-C6Ph;

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b) RF=C2F5; C3F7; C4F9; H(CF2CF2);nwhere n=1,2,3;

R1=HHCl;

R2=H

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FIELD: agriculture.

SUBSTANCE: invention relates to composition containing pirimetanyl and phosetyl-Al in weight ratio of 0.05-10 and method for healing and prophylaxis controlling of plant phytopathogenic organisms using the same. Application of phosetyl-Al to prolong pirimetanyl action also is described.

EFFECT: decreased treatment process number which is necessary to control disease progress.

8 cl, 1 ex

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1 tbl, 4 ex

FIELD: organic chemistry, chemical technology, herbicides.

SUBSTANCE: invention describes new substituted derivatives of pyrazole of the general formula (I): wherein n = 0 or 1; group A represents independently hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms or phenyl group having substituting groups optionally; group D represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkoxy-group with 1-4 carbon atoms, cycloalkyl group with 3-6 carbon atoms, halogen atom, alkoxycarbonyl group with 1-4 carbon atoms, alkylsulfonyl group with 1-4 carbon atoms or phenyl group; group E represents hydrogen atom, halogen atom or phenyl group; groups R1 and R2 both represent halogen atom; group R3 represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms or benzyl group; groups R4 and R5 are similar or different and each represents hydrogen atom, alkyl group with 1-4 carbon atoms, halogenalkyl group with 1-4 carbon atoms, cycloalkyl group with 3-8 carbon atoms that can be substituted with alkyl group with 1-4 carbon atoms, alkenyl group with 2-4 carbon atoms, alkynyl group with 2-4 carbon atoms, cyanomethyl group or phenyl group; or each R4 and R5 group means benzyl group; or each R4 and R5 group represents α- or β-phenethyl group having substituting groups at benzyl ring optionally. Indicated substituting groups represent alkoxy-groups with 1-4 carbon atoms wherein indicated substituting groups substitute hydrogen atom at the arbitrary positions 0-2 of the benzyl ring; or groups R4 and R5 form in common 5-membered or 6-membered aliphatic ring wherein the indicated ring can be substituted with alkyl groups with 1-4 carbon atoms and indicated ring can comprise one or two heteroatoms chosen from nitrogen oxygen and sulfur atom, and a method for their preparing. Also, invention describes herbicide compositions based on compound of the formula (I). Invention provides preparing herbicide compositions showing the strong herbicide effect and broad herbicide spectrum of their effect.

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7 cl, 6 tbl, 3 ex

FIELD: agriculture; chemical engineering.

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8 cl, 9 tbl

FIELD: agriculture.

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EFFECT: composition of improved quality for accelerated plant growth and development, and protection thereof from diseased.

4 cl, 4 tbl

FIELD: agriculture.

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2 tbl, 3 ex

FIELD: agriculture.

SUBSTANCE: claimed method includes plant treatment with 3-amino-2-[N-(4-fluorophenyl)carbamido]-4,6-dimethyltieno-[2,3b]-pyridine in amount of 200 g/hectare over 5 days after herbicide application to protect vegetative sunflower plants from damage action of 2,4-dichlorophenoxyacetic acid butyl ester.

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1 tbl

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EFFECT: increased plant productivity.

1 tbl

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SUBSTANCE: claimed method includes plant treatment with N-(2-methoxyphenyl)-2,6-dichloro-4-mentylnicotinamide in amount of 200 g/hectare over 5 days after herbicide application to protect vegetative sunflower plants from damage action of 2,4-dichlorophenoxyacetic acid butyl ester.

EFFECT: increased plant productivity.

1 tbl

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes a synergetic composition with the effective content of components (A) and (B) wherein (A) means herbicide chosen from the group of compounds of the formula (I): wherein R1, R2, R, X, Y and Z have values given in the invention claim or their salts; (B) means one or some herbicides among the following groups: (B1) selective herbicides with activity in some dicotyledonous cultures against monocotyledonous and dicotyledonous weeds; (B2) selective herbicides with activity in some dicotyledonous cultures against dicotyledonous weeds; (B3) selective herbicides with activity in some dicotyledonous cultures with preferable effect against monocotyledonous weeds. Also, invention describes a method for control against weeds using the proposed composition. Using the combination of proposed herbicides results to the synergetic effect.

EFFECT: valuable herbicide properties of composition.

3 cl, 7 tbl, 2 ex

FIELD: agriculture, fungicides.

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EFFECT: composition of increased fungicidal action due to synergic effect.

8 cl, 12 ex

The invention relates to chemistry and agriculture, particularly to substituted 1,3,5-triazines as promoters prorostania seeds
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