Ester compound, a composition for destroying noxious insects on its basis, the method of destroying noxious insects

 

Describes the ester compound of General formula (I), where R is methyl, ethyl, n-propyl, allyl, composition and method of destroying noxious insects. The technical result is to obtain new compounds with high activity in the destruction of harmful insects. 3 S. and 9 C.p. f-crystals, 4 PL.

The invention relates to an ester compound and pesticide containing ester compound as the active ingredient.

The aim of the present invention is a compound which has an excellent efficiency in destroying harmful parasites such as arthropods (including insects, mites, spiders, and so on) and nematodes. In the result, it was found that the ester compound of General formula I:where R represents a methyl group, ethyl, n-propyl or allyl, has a high activity in the eradication of harmful pests.

In other words, the present invention proposes an ester of the above formula (I) (hereinafter referred to as "the present compound") and a pesticide containing as an active ingredient.

The present compounds is etousa formula (II):where R is defined above, with a carboxylic acid of the following formula (III):or its reactive derivative.

Examples of the reactive derivative of carboxylic acids include halides, acid anhydrides, and the like compounds.

Preferably the reaction of the alcohol compound of the formula (II) with a carboxylic acid of formula (III) is carried out in an inert solvent, optionally in the presence of acceptable condensing agent. Preferably the reaction of the alcohol compound corresponding to the formula (II), with the above-mentioned reactive derivative is carried out in an inert solvent, optionally in the presence of a base. Examples of the condensing agent include dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (WSC) and the like compounds. The examples used bases include organic bases, such as triethylamine, pyridine, 4-dimethylaminopyridine, diisopropylethylamine and the like compounds. Examples of applicable solvents include hydrocarbons, such as benzene, toluene, hexane and the like compounds; ethers, such as diethyl ether, tetrahydro such compounds.

The duration of reaction is usually from 5 minutes to 72 hours.

The reaction is preferably carried out at a temperature ranging from minus 20oC to the boiling point of the solvent used in the reaction, or 100oS, more preferably from minus 5oC to the boiling point of the solvent used in the reaction, or up to 100oC. the Molar ratio of the alcohol compound corresponding to the formula (II), to the carboxylic acid corresponding to the formula (III), or applied reactive derivative can be set arbitrarily, but preferably is used equimolar ratio or a ratio close to equimolar. Condensing the substance or base may be used in amounts ranging from equimolar to excess, preferably from an equimolar amount to 5 moles, per 1 mole of the alcohol compound of the formula (II).

After completion of the reaction, the reaction solution may be subjected to conventional processing, such as extraction with an organic solvent, concentration and so on with the aim of obtaining this target compound. If necessary, it can be subjected to purification by standard methods, for example chromag optical isomers (R, S) and geometrical isomers (CIS/TRANS and E/Z), and all stereoisomers and mixtures thereof which possess the activity of suppressing harmful parasites that are included in the present invention.

In the above method of obtaining the original carboxylic acid corresponding to formula (III) can be synthesized, for example, by the method described in Bull. Chem. Soc. Jpn. 4385-4394 (1987).

In the above method of obtaining alcohol compound of the formula (II) used as another source reagent comprises 5-methyl-2-furfuryl alcohol, 5-ethyl-2-furfuryl alcohol, 5-propyl-2-furfuryl alcohol and 5-allyl-2-furfuryl alcohol, which can be obtained in a standard way.

Examples of harmful parasites in respect of which appears the overwhelming effect of the present compounds include the following insects, mites and ticks: Small arthropods insects (Hemiptera): Delphacidae (Delphaidae) such as Laodelphax striatellus (delphacidae brown fine), Nilaparvata lugens (delphacidae brown) and Sogatella furcifera (delphacidae white rice); cicadelloidea (cycatki) such as Nephotettix cincticeps (cycatki rice green), Nephotettia virescens (cycatki rice green) and Recilia dorsalis; Aphidoidea (aphids): bugs, such as Pentatomidae, Acanthosomatidae, Urostylidae, Dinidoridae, Coreidae and Alydidae; Aleyrodidae (be is.

The liquidation, such as Chilo suppressalis (the liquidation of rice stem), Cnaphalocrocis medinalis (rice leafroller) and Plodia Interpunctella (the liquidation barn South); Noctuidae such as Spodoptera litura (tobacco Cutworm), Pseudaletia separata ("marching worms rice), Mamestra brassicae ("marching worms cabbage); Pieridae such as Pieris-Garay crucivora (Marmite); Tortricidae such as Adoxophyes species; Carposinidae; Review; Lymantriidae (wananchi); Plusiinae; Agrotis, such as Agrotis segetum and Agrotis ipsilon (scoops Upsilon); Heliotis; Plutella xylostella (cabbage moth); Tinea pellionella (mol fur); Tineola bisselliella (mol a); and so on.

Small two-winged insects (Diptera): Type ulex, such as ulex pipiens pallens (Komar ordinary) and ulex tritaeniorhynchus; Aedes, such as Aedes aegypti and Aedes albopictus; Anopheles species, such as Anopheles sinensis; Chironomidae (midgots); Muscidae such as Musca domestica (housefly room), Muscina stabulans (fly home) and Fannia canicularis (fly small room); Calliphoridae; Sarcophagidae; Anthomyiidae such as Delia platura (fly larvae germ) and Delia antiqua (fly larvae onion); Tephritidae (fly); drosophilidae (fruit flies); Psychodidae (baboonery); Simuliidae (black flies); Tabanidae; Stomoxyidae; Ceratopogonidae (biting midges); and so on.

Coleoptera (beetles):
View Diabrotica (blaska Linosa), such as Diabrotica virgifera (blaska Dlinnaya West) and Diabrotica undcimpunctata howardi (beetle blaska odinnadtsatietazhnoe Howard); Scarabaeidae (gwic corn) and Lissorhoptrus oryzophilus (rice weevil water); Tenebrionidae (karnataki), such as Tenebrio molitor (larvae hrusica flour) and Tribolium castaneum (khruschak chestnut); Chrysomelidae, such as Phyllotreta striolata (flea earthy striped) and Aulacophora femoralis (beetle leaf pumpkin), anobiid; Epilachna such as Epilachna vigintioctopunctata (ladybug 28-point); Lyctidae (Kabushiki); Bostrychidae (Kabushiki); Cerambycidae; Paederus fuscipes (beetle); and so on.

Dictyoptera:
Blattella germanica (cockroach red); Periplaneta fuliginosa (cockroach dirty-brown); Periplaneta americana (American cockroach); Periplaneta brunnea (brown cockroach); Blatta orientalis (cockroach black); and so on.

Thysanoptera:
Thrips palmi (trips palm); Thrips hawaiiensis (flower thrips); and so on.

Hymenoptera:
Formicidae (ants); Vespid (wasps); Beiley; Tenthredinidae (these sawflies), such as Athalis rosae ruficornis (slitter cabbage); and so on.

Orthoptera:
Gryllotalpidae (mole crickets); Acridity (real locust); and so on.

Siphonaptera:
Ctenocephalides canis (dog flea); Ctenocephalides felis (cat flea); Pulex irritans (human flea); and so on.

Anoplura:
Pediulus humanus capitis; Pthirus pubis; and so on.

Isoptera:
Reticulitermes speratus; Coptotermes formosanus; and so on.

Tetranychidae:
Tetranychus cinnabarinus (clasic Carmine spider); Tetranychus urticae (clasic spider bimaculated); Tetranychus kanzawai (clasic spider is ashna dust:
Acaridae; Dermatophagoidinae; Pyroglyphinae; Cheyletidae; Macronyssidae, such as the type Ornithonyssus; and so on.

Ticks:
Ixodid ticks such as Boophilus miroplus; and so on.

This connection is used as an active ingredient of a pesticide, usually included in the formula in combination with a solid carrier, liquid carrier, gaseous carrier or bait, or used for impregnation of the carrier mosquito coils or mosquito plate designed for electrothermal fumigation.

If necessary, can be added surface-active agent, adhesive, dispersant, stabilizer and other excipients or additives.

Examples of compositions with the use of the present compounds include oil solutions, emulsifiable concentrates, wettable powders, flowable formulations, granules, dusty, aerosols, flammable or chemical fumigants, such as mosquito coils, mosquito plate for electro-thermal fumigation and porous ceramic fumigants, volatile composition, applied to the resin or paper, smoke composition, the composition ultramage volume formulas for use in very small volumes) and poisoned bait.

These compounds include n, ispolzuemykh in formulas include fine powder or granules of clays (e.g. kaolin clay, diatomaceous earth, synthetic hydroxide silica, bentonite, clay Fubasami, acid clay), talc, ceramics, other inorganic minerals (e.g. sericite, quartz, sulfur, activated carbon, calcium carbonate, a hydroxide of silicon) and chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea).

Examples of liquid media used in formulas include water, alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene and methylnaphthalene aliphatic hydrocarbons such as hexane, cyclohexane, kerosene and gas oil, esters such as ethyl acetate and butyl acetate, NITRILES, such as acetonitrile and isobutyronitrile, ethers, such as diisopropyl simple ether and dioxane, acid amides such as N,N-dimethylformamide and N, N-dimethyl-cetamide, halogenated hydrocarbons such as dichloromethane, trichloroethane and carbon tetrachloride, dimethyl sulfoxide, vegetable oils such as soybean oil and cottonseed oil.

Examples of gaseous carriers or prop the gas LPG, dimethyl simple ether and carbon dioxide.

Examples of surfactants include alkyl sulphates, alkyl sulphonates, alkylarylsulphonates, alkylsilane ethers, polyoxyethyleneglycol ethers, polietilenglikolya ethers, ethers, polyhydric alcohol and alcohol derivatives of sugars.

Examples of adhesives, dispersing agents and other auxiliary ingredients or additives include casein, gelatin, polysaccharides, such as starch, Arabic gum, cellulose derivatives and alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers such as polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acid.

Examples of stabilizers include PAP (acidic isopropylacetate), BHT (2,6-di-tert-butyl-4-METHYLPHENOL), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-metatitanate), vegetable fats, mineral oils, surfactants, fatty acids and esters of fatty acids.

As the basis for mosquito coils can be used a mixture of powder of plant material, such as wood powder and Pyrethrum Marc, and binders, such as military fumigation electric, can serve compacted fibrils of cotton fluff or a mixture of pulp and cotton fluff.

The basis of combustible fumigant comprise, for example, an exothermic substance, such as nitrate, nitrite, guanidine salt, potassium chlorate, nitrocellulose, ethylcellulose and wood powder, pyrolytic stimulating substance, such as salt of alkaline metal salt, alkaline earth metal dichromate and chromate, the source of oxygen, such as potassium nitrate, controller of combustion, such as melanin and wheat starch, a porous filler such as diatomaceous earth and a binder such as a synthetic adhesive.

The basis of the chemical fumigant comprise, for example, an exothermic substance, such as an alkali metal sulfide, polysulfide, sulfide, hydrated salt, or calcium oxide, the catalytic substance such as upholsteries substance, iron carbide and activated clay, organic foaming substance, such as azodicarbonamide, benzene-sulfonylhydrazide, N,N'-dinitrosopentamethylenetetramine, polystyrene and polyurethane, and a filler such as natural or synthetic fibers.

Examples of bases volatile agent include thermoplastic resins, filter boom of the second oil sugar and crystalline cellulose, antioxidants such as dibutylaminoethanol and nordihydroguaiaretic acid, a substance for preventing erroneous eating, such as powder, red pepper, attracting substance, such as giving to the smell of cheese, onions and peanut butter.

Fluid fundamentals usually get fine grinding of this compound at a ratio of 1 to 75 wt.% in water containing 0.5-15 wt.% dispersant, 0.1 to 10 wt.% suspending agents (for example, protective colloid or connections, giving thixotropy) and 0-10 wt.% additives (for example, protivovospalitel, corrosion inhibitor, stabilizer, regulating substances, auxiliary substances for penetration, antifreeze, bactericide, fungicide).

This connection can dispergirujutsja in oil, in which the present compound is virtually insoluble, obtaining oil suspensions.

Examples of protective colloids can serve as gelatin, casein, gum, ethers, cellulose and polyvinyl alcohol. As a substance, which imparts thixotropy, can serve as bentonite, magnesium aluminosilicate, xanthan gum or polyacrylic acid.

The resulting formulas are used as such and what Matilda, bactericide, herbicide, plant growth regulators, synergists, fertilizers or substance that alters the state of the soil, without mixing or pre-mixing.

Examples of synergists can serve the following substances: piperonylbutoxide, N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide, N-(2-ethylhexyl)-1-isopropyl-4-methyl-bicyclo[2.2.1]Oct-5-ene-2,3-dicarboximide and 1,1'-oxy-bis(2,3,3,3-tetrafluoropropene). This synergist usually applied at the rate of 0.2-50 wt.h. 1 wt.h. the present compounds. A particularly preferred combination of the present compounds and piperonylbutoxide. The mass ratio of the present compound and piperonylbutoxide usually is 1:0.2 to 1:50, preferably 1:0.5 to 1:25, more preferably 1:1-1:20.

Insecticides, acaricides and nematicides used in conjunction with the present compounds include organophosphorus compounds such as fenitrothion [0,0-dimethyl 0-(3-methyl-4-nitrophenyl)phosphorothioate], fenthion [0,0-dimethyl 0-{ 3-methyl-4-(methylthio)phenyl} -phosphorothioate] , diazinon [0,0-diethyl 0-2-isopropyl-6-methylpyrimidin-4-phosphorothioate] , chlorine pirits [0,0-diethyl-0-3,5,6-trichloro-2-pyridyl phosphorothioate] , acetat [0,S - dimethylaminopropionic], methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazole-3-ylmethyl the SFAT] , sulprofos [0-ethyl 0-4-(methylthio)phenyl S-propylphosphonate], cyanophos [0-4-cyanophenyl 0,0-dimethyl phosphorothioate] , dioxobenzo [2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide] , timeout [0,0-dimethyl S-methylcarbamoylmethyl phosphorodithioate], pentat [ethyl, dimethoxyphenylthio(phenyl)acetate] , Malathion [1,2-bis(etoxycarbonyl)ethyl 0,0-dimethylphosphorodithioate] , trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate] , azinphosmethyl [0,0-dimethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithioate], monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)-vinylfast], ation [0,0,0',0'-tetraethyl S, S'-methylene bis(phosphorodithioate)], urethane compounds, such as fenobucarb [2-Deut-butylphenyl methylcarbamate], benfuracarb [ethyl N-[2,3-dihydro-2,2-dimethylbenzofuran-7-jocstarbunny(methyl)aminothio] -N-isopropyl--alaninate], propoxur [2-isopropoxyphenyl methylcarbamate] , carbosulfan [2,3-dihydro-2,2-dimethylbenzofuran-7-yl(dibutylamino)methylcarbamate], carbaryl [1-naphthyl methylcarbamate] , methomyl (S-methyl N-(methylcarbamoyl)thioacetimidate], ethiofencarb [2 -(ethylthiomethyl) fenilmetilketenom], aldicarb [2-methyl-2-(methylthio)Propionaldehyde 0-methylcarbamoylmethyl] , oxamyl [N,N-dimethyl-2-methylcarbamoylmethyl)-1,3,4-oxadiazol-2-(3H)-he] , PYRETHROID compounds such as etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl simple ether], fenvalerate [-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate] , esfenvalerate [(S)--cyano-3-phenoxybenzyl (S)-2-(4-course)-3-methylbutyrate], fenpropathrin [-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate] , cypermethrin [-cyano-3-phenoxybenzyl-3-(2,2-dichlorovinyl)-2,2 - dimethylcyclopropanecarboxylate] , permethrin [3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate] , cyhalothrin [-cyano-3-phenoxybenzyl (Z)-3-(2-chloro-3,3,3 - Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate] , Delta-methrin [(S)--cyano-3-phenoxybenzyl- (1R)-CIS-3- (2,2 - dibromovinyl)-2,2-dimethylcyclopropanecarboxylate] , cicloprofen [-cyano-3-phenoxybenzyl-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate] , fluvalinate [-cyano-3-phenoxybenzyl N-(2-chloro-,,-Cryptor-paratool)-D-valinnat] , bifenthrin [2-methylbiphenyl-3-ylmethyl (Z)-3-(2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-keiltm src="https://img.russianpatents.com/chr/945.gif">-cyano-3-phenoxybenzyl (1R, CIS)-3-(1,2,2,2-tetrabromide)-2,2-dimethylcyclopropanecarboxylate] , selflove [(4-ethoxyphenyl) [3-(4-fluoro-3-phenoxyphenyl)propyl] dimethylsilane] , d-phenothrin [3-phenoxybenzyl (1R)-Hrizantema] , cyphenothrin-cyano-3-phenoxybenzyl (1R)-Hrizantema] , d-resmethrin [5-benzyl-3-furylmethyl (1R)-Hrizantema] , acrinathrin [(S)--cyano-3-phenoxybenzyl (Z)-(1R, CIS)-2,2-dimethyl-3-[2-(2,2,2-Cryptor-1-triftormetilfullerenov) vinyl]-cyclopropanecarboxylate] , cyfluthrin [-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate], tefluthrin [2,3,5,6-titrator-4-methylbenzyl (Z)-3-(2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethyl-eloprofessional] , transfluthrin [2,3,5,6-tetrafluorobenzyl (1R, TRANS)-3-(2,2-dichlorovinyl] -2,2-dimethylcyclopropanecarboxylate] , tetramethrin (3,4,5,6-tetrahydropyrimidine Hrizantema], allethrin [3-allyl-2-methyl-4-oxocyclopent-2-enyl Hrizantema] , prallethrin [(S)-2-methyl-4-oxo-3-(2-PROPYNYL)cyclopent-2-enyl (1R)-Hrizantema] , empenthrin [(E)-1-ethinyl-2-methyl-2-pentenyl (1R)-Hrizantema] , imiprothrin [2,5-dioxo-3-(prop-2-inyl)imidazolidin-1-ylmethyl (1R)-Hrizantema] , d-permethrin [5-(prop-2-inyl)furfuryl (1R)-Hrizantema] and 5-(prop-2-inyl)turf is but-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one] , derivatives of nitroimidazolidin, derivatives nereistoxin, such as cartap [S,S'-(2-dimethylaminomethylene) bis(THIOCARBAMATE)] , thiocyclam [N,N-dimethyl-1,2,3-trician-5-ylamine] and bensultap [S,S'-2-dimethylaminomethylene di(benzothiazolone)], derivatives of N-canamedia, such as N-cyano-N'-methyl-N'-(6-chloro-3-pyridylmethyl)acetamidine, chlorinated hydrocarbons, such as endosulfan [6,7,8,9,10,10-hexachloro-1,5,5 and, 6,9,9-hexahydro-6,9-methane-2,4,3-benzodioxathiepin 3-oxide] ,-ANS [1,2,3,4,5,6-hexachlorocyclohexane] and dicofol [2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethanol], derived benzoylphenyl-urea, such as chlorfluazuron [1-[3,5-dichloro-4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-differentail) urea], teflubenzuron [1-(3,5-dichloro-2,4-differenl)-3-(2,6-differentail) urea] and flufenoxuron [1-[4-(2-chloro-4-triptoreline)-2-forfinal] -3-(2,6-differentail) urea] , derivatives of formamidine, such as amitraz [N - methylbis(2,4-xylylenediamine)Amin] and Chlordimeform [N'-(4-chloro-2-were)-N,N-dimethylethanamine], thiourea derivatives, such as diafenthiuron [1-tert-butyl-3-(2,6-aminobutiramida 4-phenoxyphenyl)thiourea], derivatives phenylimidazole, derivatives phenylpyrazole, bromopropylate [isopropyl 4,4'-dithiocarbonate] , propargite [2-(4-tert-butylphenoxy)cyclohexyl prop-2-inyl the sulfite] , fenbutatin [bis[Tris(2-methyl-2-phenylpropyl)tin]oxide], hexythiazox [TRANS-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-3-thiazolecarboxamide] , clofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine] , pyridaben [2-tert-butyl-5-(4-tert-butylbenzyl)-4-chloro - pyridazin-3(2H)-he], fenpyroximate [tert-butyl(E)--(1,3-dimethyl-5-Phenoxyethanol-4-ylmethylamino)-partaloa] , tebufenpyrad [N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1-methyl-pyrazole-5-carboxamide], pyrimidifen [5-chloro-N-[2-[4-(2- ethoxyethyl)-2,3-dimethylphenoxy]ethyl] -6-ethylpyrimidine-4-amine] , abamectin, milbemectin, ivermectin, azadirachtin [AZAD] and polyactive complexes, including tetradactyl, dynactin and tinactin.

When the present compound is used as an active ingredient in pesticides for agricultural purposes, the consumption of 1000 m2is usually from 5 to 500, Emulsifiable concentrates, wettable powders and flowable formulations are diluted with water to a concentration of 0.1-1000 hours/million Pellets and dusty not diluted and used as they are prepared.

When the application of the present compounds as an active ingredient in pesticides home desig is s, wettable powders and flowable formulations diluted with water to concentrations of 0.1-10000 hours/million Oil solutions, aerosols, fumigants, volatile agents, fogging agents, compositions with ultraslim volume of toxic baits and retinoid or sheet compositions are used as they are prepared.

Moreover, the present compound can form a composition with one or more subliminality substances. Such a composition may be in the form of tablets, which is obtained by curing a mixture of this compound and subliminales substance, melting by heating, and compressing the mixture under pressure of 3-15 kg/cm2. The contents of this connection in the tablet usually is 1-25 wt. %. Subliminale substances include 2,4,6-triisopropyl-1,3,5-trioxane, tricyclo[5,5,1,0] Dean, acetonates, amicable, BUTYLCARBAMATE, parabolically, chloroacetanilide, 4-chloro-3-METHYLPHENOL, cyclohexanone, diacetone, digitoxigenin, dimetilan salad, dimethylene, furfurylated, paradichlorobenzene, naphthalene, camphor, etc., the Composition may facilitate the volatilization of the present compounds with sublimiruet substance at room temperature. Therefore, the composition is very effective against flying is, moth and a beetle Paederus fuscipes. As mentioned above subliminale substances possess insecticidal activity, you can expect the manifestation of incremental or synergistic effect.

The flow rate and concentration of the composition may vary arbitrarily in accordance with the type of composition, time, place and manner of treatment, insect pests and caused damage.

Examples
Further, the invention is additionally illustrated by the examples of the preparation examples of compounds and biological tests.

Example obtain 1
(1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (2282 mg) was added while cooled on ice to a solution mixture of 5-methyl-2-furfuryl alcohol (1000 mg), 2,6-di-tert-butyl-4-METHYLPHENOL (5 mg), pyridine (1057 mg) and 30 ml of toluene and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into 5% aqueous citric acid solution under ice cooling and was extracted three times with diethyl ether. The combined ether layer was sequentially washed with saturated sodium bicarbonate solution and saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of the solvent under vacuum, the resulting residue ACC is 5-methyl-2-furfuryl (1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (1)].

The output is 83%, nD29=1,4681.

1H-NMR (internal standard: tetramethylsilane was in CDCl3)value (ppm) 1.28 (s, 3H), 1.29 (s, 3H), 2.00 (d, 1H), 2.16 (DD, 1H), 2.31 (s, 3H), 5.00 (s, 2H), 5.92 (d, 1H), 6.28 (d, 1H), 6.92 (d, 1H).

Example of getting 2
(1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (2070 mg) was added while cooled on ice to a solution mixture of 5-methyl-2-furfuryl alcohol (1000 mg), 2,6-di-tert-butyl-4-METHYLPHENOL (5 mg), pyridine (941 mg) and 30 ml of toluene and the mixture was stirred at room temperature for 8 hours. The reaction mixture was poured into 5% citric acid solution under ice cooling and was extracted three times with diethyl ether. The combined ether layer was sequentially washed with saturated sodium bicarbonate solution and saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of the solvent under vacuum, the resulting residue was subjected to chromatographic purification on a column of silica gel (eluent: n-hexane/ethyl acetate=30/1) and received 2270 mg 5-methyl-2-furfuryl (1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [nesian in CDCl3)value (ppm) 1.23 (t, 3H), 1.29 (s, 3H), 1.31 (s, 3H), 2.01 (d, 1H), 2.18 (DD, 1H), 2.66 (q, 2H), 5.01 (s, 2H), 5.95 (d, 1H), 6.30 (d, 1H), 6.93 (d, 1H).

Example of getting 3
(1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (1303 mg) was added while cooled on ice to a solution mixture of 5-propyl-2-furfuryl alcohol (700 mg), 2,6-di-tert-butyl-4-METHYLPHENOL (5 mg), pyridine (592 mg) and 30 ml of toluene and the mixture was stirred at room temperature for 8 hours. The resulting mixture is then subjected to processing in accordance with the method of example receive 1 and receive 1350 mg 5-propyl-2-furfural (1RS, CIS)-3-(Z-2-chloro-3,3,3-cryptographp-1-enyl)-2,2 - dimethylcyclopropanecarboxylate [present compound (3)].

The output is 74%, nD29=1,4671.

1H-NMR (internal standard: tetramethylsilane was in CDCla)value (ppm) 0.98 (t, 3H), 1.28 (s, 3H), 1.29 (s, 1H), 1.58-1.78 (m, 2H), 2.01 (d, 1H), 2.18 (DD, 1H), 2,61 (t, 2H), 5.02 (s, 2H), 5.93 (d, 1H), 6.28 (d, 1H), 6.95 (d, 1H).

Example 4
(1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate (28 mg) was added while cooled on ice to a solution mixture of 5-allyl-2-furfuryl alcohol (10 mg), 2,6-di-tert-butyl-4-METHYLPHENOL (5 mg), pyridine (13 mg) and 5 ml of toluene and the mixture videri the methodology on the example of getting 1 and 17 mg of 5-allyl-2-furfural (1RS, CIS)-3-(2-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2 - dimethylcyclopropanecarboxylate [present compound (4)].

Outlet - 65%, nD29=1,4759.

1H-NMR (internal standard: tetramethylsilane was in CDCl3)value (ppm) 1.29 (s, 3H), 1.30 (s, 3H), 2.01 (d, 1H), 2.15 (DD, 1H), 3.41 (d, 2H), 5.01 (s, 2H), 5.08-5.21 (m, 2H), 5.84-5.97 (m, 2H), 5.98 (d, 1H), 6.31 (d, 1H), 6.91 (d, 1H).

Example of getting 5
5-methyl-2-furfuryl (1R, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (5)] can be obtained by using (1R, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2 - dimethylcyclopropanecarboxylate instead of (1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)- 2,2-dimethylcyclopropanecarboxylate in the Example of obtaining 1.

An example of obtaining 6
5-methyl-2-furfuryl (1R, TRANS)-3-(Z-2-chloro-3,3,3 - Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (6)] can be obtained by using (1R, TRANS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate instead of (1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate in the Example of obtaining 1.

Examples of obtaining 7-9
5-ethyl-2-furfuryl (1R, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2, 2-dimethylcyclopropanecarboxylate [present compound (7)],
5-propyl-2-furfuryl (1R, CIS)-3-(Z-2-chloro-3,3,3 - Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (9)], can be obtained by using (1R, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate instead of (1RS, CIS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylic-chloride in Examples get 4-6.

Examples get 10-12
5-ethyl-2-furfuryl (1R, TRANS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (10)],
5-propyl-2-furfuryl (1R, TRANS)-3-(Z-2-chloro-3,3,3 - Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (11)], and
5-allyl-2-furfuryl (1R, TRANS)-3-(Z-2-chloro-3,3,3 - Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate [present compound (12)] can be obtained by using (1R, TRANS)-3-(Z-2-chloro-3,3,3-Cryptocom-1-enyl)-2,2-dimethylcyclopropanecarboxylate instead of (1RS, CIS)-3-(Z-2-[chloro-3,3,3-Cryptocom - 1-enyl)-2,2-dimethylcyclopropanecarboxylic-chloride in Examples get 4-6.

Alcohol compounds corresponding to formula (II) used in the above examples, obtain, can be synthesized in accordance with the following example.

Getting 5-methyl-2-furfuryl alcohol
To a mixture of 5-methylpyrrole (3 g) and methanol (30 ml) and cooled with ice was added borohydride sodium (515 mg) and the mixture paramasivam and was twice extracted with diethyl ether. The combined ether layer was sequentially washed with saturated sodium bicarbonate solution and saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of the solvent under vacuum, the resulting residue was passed through a chromatographic column filled with silica gel, obtaining 2.3 g of 5-methyl-2-furfuryl alcohol.

The yield is 75%.

1H-NMR (internal standard: tetramethylsilane was in CDCl3)value (ppm) 1.71 (t, 1H), 2.31 (d, 3H), 4.53 (d, 2H), 5.96 (d, 1H), 6.17 (d, 1H).

Getting 5-ethyl-2-furfuryl alcohol
In a nitrogen atmosphere to a mixture of furfuryl alcohol (5 g) and tetrahydrofuran (75 ml) at -78oWith the solution was added n-utility in n-hexane (1,69 M, 69,5 ml) and the mixture was stirred for 1 hour. After adding to the mixture of ethyliodide (9.6 g) and the mixture was stood at room temperature and was stirred for 8 hours. The reaction mixture was poured into 5% aqueous citric acid solution under ice cooling and was twice extracted with diethyl ether. The combined ether layer was sequentially washed with saturated sodium bicarbonate solution and saturated NaCl solution and dried over anhydrous magnesium sulfate. After removal of the solvent under vacuum, the resulting residue p is

1H-NMR (internal standard: tetramethylsilane was in Dl3)value (ppm) 1.22 (t, 3H), 1.72 (t, 1H), 2.62 (sq. 2H), 4.56 (d, 2H), 5.91 (d, 1H), 6.19 (d, 1H).

Getting 5-propyl-2-furfuryl alcohol
In a nitrogen atmosphere to a mixture of furfuryl alcohol (5 g) and tetrahydrofuran (75 ml) at -78oWith the solution was added n-utility in n-hexane (1,69 M, 70 ml) and the mixture was stirred for 1 hour. After adding to the mixture of propyliodide (10.4 g) and the mixture was stood at room temperature and was stirred for 8 hours. The reaction mixture was subjected to subsequent processing in accordance with a procedure similar to that described above, and was obtained 1.2 g of 5-propyl-2-furfuryl alcohol.

1H-NMR (internal standard: tetramethylsilane was in CDCl3)value (ppm) 0.98 (t, 3H), 1.53-1.72 (m, 2H), 1.82 (user, 1H), 2.58 (t, 2H), 4.52 (user, 2H), 5.40 (d, 1H), 6.15 (d, 1H).

Getting 5-allyl-2-furfuryl alcohol
In a nitrogen atmosphere to a mixture of furfuryl alcohol (5 g) and (75 ml) of tetrahydrofuran at -78oWith the solution was added n-utility in n-hexane (1,69 M, 70 ml) and the mixture was stirred for 1 hour. After adding to the mixture of Allilueva (10.3 g) and the mixture was stood at room temperature and was stirred for 8 hours. Rea who was alocale 0.87 g of 5-allyl-2-furfuryl alcohol.

1H-NMR (internal standard: tetramethylsilane was in CDCl3)value (ppm) 1.72 (user, 1H), 3.40 (d, 2H), 4.52 (d, 2H), 4.92-5.25 (m, 2H), 5.65-5.98 (m, 1H), 5.98 (d, 1H), 6.19 (d, 1H).

Below are examples of compounds. Specified in the examples, parts are massive.

Example of structure 1. Mulgirigala concentrates
20 hours of each of compounds (1) to(12) according to the invention was dissolved in 65 hours xylene, mixed with 5 hours of Sarpola H (surfactant from the company That chemical Co., LMT. ), and thoroughly mixed, with a share of 20% mulgirigala concentrates for each connection.

Example of compound 2. Wettable powders
40 hours of each of compounds (1) to(12) was first mixed with 5 hours of Sarpola H, and then with 32 hours of Complexa #80 (fine powder of synthetic hydroxide of silicon from the company Shionogi & Co., Ltd.) and 23 hours diatomaceous earth with a particle size of 300 mesh and mixed, receiving 40% wettable powder for each compound.

Example of compound 3. Granules
1,5 hours of each of compounds (1) to(12) were mixed with 98,5 including AGSORB LVM-MS 24/48 (granular media from calcined montmorillonite having a particle diameter within 24-48 mesh, company OIL DRI Corp.), getting a 1.5% pellets for each connection.

Example of compound 4. Microcapsules
A mixture of 10 hours each connection to 20 hours a 10% aqueous solution of Arabian gum and stirred in a homogenizer, obtaining an emulsion having the average particle diameter of 20 μm. The emulsion was further mixed with 2 hours of ethylene glycol and the reaction was carried out in a water bath at 60oWith in 24 hours, receiving microencapsulated slurry.

The thickener was obtained by dispersion of 0.2 tsp xanthan gum and 1.0 hours of Beegum R (magnesium aluminosilicate company Sansyo Co., Ltd) 56,3 including deionized water.

A mixture of 42.5 hours specified above microencapsulated slurry 57.5 hours specified above thickener for each connection received 10% microencapsulated formulations.

Example of compound 5. Fluid compositions
A mixture of 10 hours each of compounds (1) to(12) and 10 hours of phenylxylylethane was added to 20 hours 10%-aqueous solution of polyethylene glycol and stirred in a homogenizer, obtaining an emulsion with an average particle size of 3 microns.

The thickener was prepared, dispersive 0,2 including xanthan gum and 1.0 PM Beegum R 58,8 including deionized water.

Mixed 40 including the above emulsion and 60 hours specified thickener, receiving for each compound (10%) fluid compositions.

Example of compound 6. Dusty
5 hours of each of compounds (1) to(12) were mixed with 3 hours of Complexa #80, 0,3 including PAP and 91,7 including terrastore
of 0.1 PM of each of compounds (1) to(12) was dissolved in 5 hours dichloromethane and mixed with 94,9 including deodorized kerosene, receiving for each connection of 0.1% oil solutions.

Example of compound 8. Aerosol oil-based
The aerosol container filled with a solution obtained by dissolving 1 tsp of each of compounds (1) to(12) with dichloromethane and 5 hours 34 hours deodorized kerosene. The balloon is then supplied by the valve and through the valve to the specified aerosol container under pressure loaded 60 hours of propellant (liquefied petroleum gas), receiving for each connection aerosol oil-based.

Example of compound 9. The aerosol water-based
The aerosol container was filled with 50 hours of deionized water and a mixture of 0.6 hours each connection (1)-(12) according to the invention, 5 hours xylene, 3,4 including deodorized kerosene and 1 o'clock Atmos 300 (emulsifier from Atlas Chemical Co.). The tank was supplied with the valve and through the valve into the aerosol container under pressure filed 40 hours of propellant (liquefied petroleum gas), thereby obtaining for each connection aerosol water-based.

An example of the structure 10. Mosquito coils
A solution of 0.3 g of each of compounds (1) to(12) in 20 ml of acetone is homogeneous mixed with 99,7 g media protivomoskitnye water mixture is efficiently stirred, cooked and dried for making mosquito coils each connection.

Example of compound 11. Mosquito plate for fumigation electric
Prepared 10 ml of a solution of 0.8 g of each of compounds (1) to(12) and 0.4 g of piperonylbutoxide in acetone. The base material is uniformly impregnated with 0.5 ml of the obtained solution (plate pressed fibers of a mixture of pulp and cotton Linter: 2,5x1,h,3 cm), receiving for each connection samples of mosquito plates.

An example of the structure 12. Solutions for fumigation with electric heating
Three parts of each of compounds (1) to(12) was dissolved in 97 hours deodorized kerosene. The prepared solution was loaded into the cylinder of PVC. The balloon was inserted porous adsorption cartridge filled with the inorganic powder, utverzhdennym binder and then calcined, while the upper part of the cartridge can be heated from the heater, thereby obtaining fumigation devices electrically heated, using the liquid from each connection.

Example of compound 13. The fumigants
A porous ceramic plate (4,h,h,2 cm) was soaked with a solution of 100 mg of each of compounds (1) to(12) in a suitable amount of acetone, getting fumigants for each connection is whether a solution of 100 μg of each of the present compounds (1) to(12) in an appropriate amount of acetone and the acetone evaporated, receiving for each of the compounds volatile compounds.

Example of compound 15. Acaricide sheets
Filter paper was soaked with a solution of each of the present compounds (1) to(12) in acetone, so that the flow rate of each connection according to the invention was 1 g/1 m2and the acetone evaporated, getting acaricide sheets for each connection.

Example 16. Tablets
Was mixed with 0.1 g of each of the present compounds (1) to(12)
and 1.1 g of paradichlorbenzene, melted by heating, the mixture was poured into a form and utverjdali, receiving the tablets of each of the compounds.

The tests of these compounds as active ingredients of pesticides. In the description below is used as the reference compound (racemic compound) shown in Table 1 symbols.

Biological experiment 1
Emulsifiable concentrates were prepared for each of these compounds in accordance with the Example of structure 1. 13 g of synthetic lures for tobacco Cutworm (Spodoptera litura) were placed in a polyethylene Cup (diameter 11 cm) and was infiltrated with 2 ml of the emulsion prepared by dilution of the emulsifiable concentrates with water to a concentration of 500 PM/million Ten larvae of Spodoptera litura 4-stage was placed in a polyethylene Cup. is have 100% mortality of larvae.

Biological experiment 2
The stems of the rice plants were immersed for one minute in water emulsion concentration of 500 PM /million obtained by dilution of each emulsifiable concentrate of the present compounds prepared in accordance with Example 1 composition. The stems of the rice plants were air-dried and placed in a polyethylene Cup with a diameter of 5.5 cm, where pre-laid filter paper with a diameter of 5.5 cm, soaked in 1 ml of water. In a plastic Cup was placed about 30 larvae of delgaldo brown (Nilaparvata lugens). Mortality was checked after six days. During the experiment established that these compounds(1), (2), (3) and (4) cause the death of 90% of the larvae and more.

Biological experiment 3
At the bottom of a polyethylene Cup with a diameter of 5.5 cm was placed filter paper of the same size. On paper poured dropwise 1 ml water emulsion concentration 50 PM/million, which was obtained by dilution of the emulsifiable concentrate of each compound (1) prepared in accordance with Example 1 composition, and in a plastic Cup was placed about 30 eggs beetles flea beetles odinnadcatiletnij Howard (Diabrotica undecimpunctata howardi) and as bait one sprouted shoot of grass. Mortality waved the mortality.

Biological experiment 4
At the bottom of a polyethylene Cup with a diameter of 5.5 cm was placed filter paper of the same size. Then on paper dropwise poured in 0.7 ml water emulsion concentration of 500 PM/million obtained by dilution of the emulsifiable concentrate prepared in accordance with Example 1 composition and evenly dissipated, 30 mg of sucrose as bait. 10 female flies bedroom (Musca domestica), which have low sensitivity to pyrethroids, was left in a Cup with a lid. Mortality was determined after one day. It is established that these compounds(1), (2), (3) and (4) cause 100% mortality.

Biological experiment 5
At the bottom of a polyethylene Cup with a diameter of 5.5 cm was placed filter paper of the same diameter. Then on paper dropwise poured in 0.7 ml water emulsion concentration of 500 PM/million obtained by dilution of each emulsifiable concentrate prepared in accordance with Example 1 composition and evenly sprinkled, 30 mg of sucrose as bait. 2 individuals males of the cockroach red (Battella germanica), which are resistant to pyrethroids, was left in a Cup with a lid. Mortality was determined after six days. It is established that these compounds (the dilution of the emulsifiable concentrate, prepared for each of the present compounds in accordance with the Example 1 composition was added to 100 ml water, deionized with ion-exchange resin (concentration of active ingredient of 3.5 hours/million). 20 larvae of the last stage of ordinary mosquito (Culex pipiens paliens) was left in the water. The results of biological experiments in respect of the ordinary mosquito was determined after one day. It is established that these compounds(1), (2), (3) and (4) cause 90% mortality and higher.

Biological experiment 7
10 female individuals of ordinary mosquito (Culex pipiens pallens) were placed in a glass cube size(HH cm, 0,34 cm3). Spray under pressure of 0.8 ATM sprayed 0.7 ml of 0.1% oil solution prepared for each of these compounds in accordance with the Example of composition 7. Within 15 minutes we determined the extent of destruction of mosquitoes. It is established that these compounds(1), (2), (3) and (4) cause 90% mortality of mosquitoes and above.

Biological experiment 8
In accordance with Example 10 of the compounds according to the invention prepared with mosquito coil containing the present compound in the amount of 0.3%. 10 female individuals of ordinary mosquito (Culex pipiens pallens) were placed in a glass cube of the size of the ku. After 15 minutes was determined by the amount of infected mosquitoes. It is established that the compounds according to the invention(1), (2), (3) and (4) strike 100% of mosquitoes.

Biological experiment 9
The solution of each of the present compounds in acetone was applied on 10 female flies bedroom (Afusca domestica), on the back of the thoracic area, at a rate of 5 μg of active ingredient per fly, and left flies with water and food. The percentage of deaths was determined after 24 hours (two groups). It is established that these compounds(1), (2), (3) and (4) cause 100% mortality.

Biological experiment 10
In an aluminum Cup having a bottom diameter 7 cm, poured dropwise of 0.64 ml of 0.05% (wt./about.) solution of these compounds in the acetone and then the acetone was evaporated in the air. 10 female flies bedroom (Musca domestica) were placed in a polyethylene Cup (diameter 9 cm, depth 4.5 cm) and the Cup was closed with nylon mesh 16 mesh to prevent direct contact of houseflies with the connection. Upside-down plastic Cup covered with aluminum Cup at 25oWith 120 minutes. Then a polyethylene Cup was removed from the aluminum Cup and house flies were given water and food. After 24 hours was determined by the percentage of the dead (two repetitions). It is established that this is, having a bottom diameter 7 cm, poured dropwise of 0.64 ml of 0.05% (wt./about.) solution of these compounds in the acetone and then the acetone was evaporated in the air. 10 female individuals of ordinary mosquito (Culex pipiens pallens) were placed in a polyethylene Cup (diameter 9 cm, depth 4.5 cm) and the Cup was closed with nylon mesh 16 mesh to prevent direct contact of mosquitoes with the connection. Upside-down plastic Cup covered with aluminum Cup at 25oWith 120 minutes. Then a polyethylene Cup was removed from the aluminum Cup and the mosquitoes were given water and food. After 24 hours was determined by the percentage of the dead (two repetitions). It is established that these compounds(1), (2), (3) and (4) cause 100% mortality.

Biological experiment 12
Each of these compounds, diluted with acetone to a certain concentration, were applied to 10 larvae middle stage of a moth (Tineola bisselliella) in the Central part of the backrest, the active ingredient in the dosage of 3 mg one insect. As a food moth gave a wool muslin (2x2 cm). After 7 days was determined by the mortality of the larvae of the moth and the degree of damage to wool fabric (two repetitions). It is established that the application of the present compounds(1), (2), (3) and (4) causes 100%-n is as mortality and no significant tissue damage.

Biological experiment 13
A piece of woolen cloth muslin (2x2 cm) were placed on the bottom of a polyethylene Cup (diameter of the bottom 10 cm, the diameter of the top open part of 12.5 cm, height 9.5 cm, volume 950 cm3). 10 larvae middle stage of a moth (inl bisselliella) were placed in a Cup, and each of volatile substances, prepared in accordance with Example composition 14, hung to cover the inside of the cups. After aging for one week at 25oWith the Cup was discovered and determined the mortality of the larvae of the moth and damage to wool fabric muslin clothes moth (two repetitions). The experiment established that the use of these compounds(1), (2), (3) and (4) causes 100% mortality and the absence of tissue damage.

Biological experiment 14
The square of filter paper with the side of 3.2 cm was treated with 36 mg of each of these compounds, and two pieces of woolen cloth muslin (25x25 cm) was suspended in the upper part of the corrugated cardboard box (size HH cm). After aging at 25oC and humidity of 60% for one week at the top of the box was hung two tea strainer containing 7-10 larvae middle stage of a moth (Tineola bisselliella) and one piece of woolen cloth macindoe her tissue damage. Similar experiments repeated aged two, three and five weeks after treatment to determine the duration of this connection. The results are shown in Table 2. The degree of damage marked "-" in the absence of lesions, "+" - minor damage, "++" - serious damage and "+++" - heavy damage.

Biological experiment 15
The present compound (1) was added specified in Table 3 the number of piperonylbutoxide. The quantitative ratio of piperonylbutoxide to this connection was 0-, 2-, 4-, 8- and 16-fold. The mixture was dissolved in acetone. An acetone solution (5 μl) was applied on 10 female flies bedroom {Musca domestica) in the thoracic area from the back. After 24 hours to determine the number of dead insects (2 repeats) and calculated mortality. The results are shown below in Table 3.

Stability tests
In acetone was dissolved each of the present compounds (3,3 mg) and cooked acetone solution was impregnated filter paper (size 2x1,5 cm) and dried in the air. Separately filter paper treated with powder brass [in filter paper with a diameter of 5.5 cm, in one surface rubbed the powder brass (copper/zinc 76-78/22-24) about 0.03 mg/cmth filter paper was placed between the two halves of the folded half of the filter paper, recorded clip and placed in a laminated aluminum bag. The package tightly closed heat soldering and maintained in the vessel at a constant temperature of 60oWith in 48 hours. Then the package was opened and the filter paper treated brass powder was tested for color change and odor. The result is stated that if any of the present compounds (1)-(4) no change in color or odor.

Change color part of the service, which uses copper jewelry or painted copper-containing dyes, or cause sometimes unpleasant smell caused PYRETHROID compounds in harsh conditions. The experiments showed that these compounds even under severe conditions cause no odor or discoloration.

Toxicity tests
The present compound (1) was diluted in corn oil to the appropriate concentration. After a 20-hour exposure of rats without food four 7-week old male rats were forcibly introduced into the stomach of the diluted solution at a rate of 0.1 ml / 10 g weight of the animal. Four hours after injection of the solution, the rats were given food itively LD50. The results are shown in Table 4.

These compounds have excellent efficacy in suppressing harmful insects, and especially the present compound in which R represents a methyl group, has an excellent pesticidal activity and low toxicity.


Claims

1. Ester compound of General formula (I)

where R is a methyl group, ethyl, n-propyl or allyl.

2. Ester compound under item 1, where R is methyl.

3. Ester compound under item 1, where R is ethyl.

4. Ester compound under item 1, where R is n-propyl.

5. Ester compound under item 1, where R is allyl.

6. Composition for destruction of harmful insects, which comprises the ester compound under item 1 as an active ingredient and a carrier.

7. The composition for exterminating harmful insects under item 6, characterized in that it further includes subliminale substance.

8. The composition for exterminating harmful insects under item 7, characterized in that as subliminales substance containing para-dichlorobenzene.

9. The composition for exterminating harmful insects under item 6, characterized in that zapolni as a synergist contains piperonylbutoxide.

11. The composition for exterminating harmful insects under item 6, characterized in that the mass ratio of ester compounds on p. 1 to piperonylbutoxide is in the range from 1: 1 to 1: 20.

12. Method of destroying noxious insects, which includes the processing of the insects or their habitat ester compound under item 1.

 

Same patents:

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 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: 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

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