Pyrethroid pesticide

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

 

The technical field

The present invention relates to an ester compound and its use as a pesticide.

The level of technology

There are many PYRETHROID compounds designed for use as pesticides. In Pestic. Sci., 1976, 7, pp.499-502, described 5-benzyl-3-furylmethyl 2,2-dimethyl-3-(2-cyano-3-ethoxy-3-oxo-1-propenyl)cyclopropanecarboxylate.

The invention

The present invention relates to ester compounds of the following formula (1):

In particular, the present invention relates to 5-benzyl-3-furylmethyl 2,2-dimethyl-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate represented by the formula (1) (hereafter referred to as “the present compound”); pesticide composition comprising the present compound as an active ingredient and an inert carrier; and a method of combating pests comprising applying an effective amount of the present compounds on insects or their habitat.

Embodiments of the invention

The present invention has the isomers associated with the presence of two asymmetric carbon atoms on tsiklopropanovom ring, and isomers associated with a double bond. The present invention includes any active isomers and compounds containing isomeric any value.

Embodiments of the present invention include, for example, the following connections:

- ester compound of formula (1)in which absolute configuration position 1 on tsiklopropanovom ring is an R configuration;

- ester compound of formula (1)in which a relative configuration of the substituent in position 1 cyclopropanol ring and the substituent at position 3 cyclopropanol ring is transconfiguration;

- ester compound of formula (1)in which absolute configuration position 1 on tsiklopropanovom ring is an R configuration and a relative configuration of the substituent in position 1 cyclopropanol ring and the substituent at position 3 cyclopropanol ring is transconfiguration;

- ester compound of formula (1)containing 80% or more of the isomer having the absolute configuration position 1 on tsiklopropanovom ring, representing the R-configuration;

- ester compound of formula (1)containing 80% or more of the isomer having the relative configuration of the substituent in position 1 cyclopropanol ring, and the substituent in position 3 cyclopropanol ring has transconfiguration;

- ester compound of formula (1)containing 80% or more of the isomer having the absolute configuration is the reference position 1 on tsiklopropanovom ring, representing the R-configuration and the relative configuration of the substituent in position 1 cyclopropanol ring, and the substituent in position 3 cyclopropanol ring has transconfiguration;

- ester compound of formula (1)containing 90% or more of the isomer having the absolute configuration position 1 on tsiklopropanovom ring, representing the R-configuration;

- ester compound of formula (1)containing 90% or more of the isomer having the relative configuration of the substituent in position 1 cyclopropanol ring, and the substituent in position 3 cyclopropanol ring has transconfiguration;

- ester compound of formula (1)containing 90% or more of the isomer having the absolute configuration position 1 on tsiklopropanovom ring, representing the R-configuration and the relative configuration of the substituent in position 1 cyclopropanol ring, and the substituent in position 3 cyclopropanol ring has transconfiguration.

This connection can be obtained, for example, a method of obtaining 1 and the method of obtaining 2.

The method of obtaining 1

The present compound can be obtained by reacting 5-benzyl-3-furylmethanol represented by the formula (2) (hereinafter called “compound (2)”), 2,2-dime the Il-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylic acid, represented by formula (3) (hereafter referred to as “compound 3”), in the presence of a condensing agent.

Communication is usually carried out in a solvent. Used when interacting solvent includes, for example, aliphatic hydrocarbons such as hexane, heptane, octane, Noonan and the like; aromatic hydrocarbons such as toluene, xylene, mesitylene and the like; halogenated hydrocarbons such as 1,2-dichloroethane, chlorobenzene, dichlorobenzene, benzotrifluoride and the like; ethers such as diisopropyl ether, 1,4-dioxane, tetrahydrofuran, etilenglikolevye ether and the like; diethylethylenediamine ether and the like; acid amides such as N,N-dimethylformamide and the like; sulfoxidov, such as dimethylsulfoxide, sulfolan etc.; as well as their mixture.

Used in the interaction of the condensing agent includes, for example, carbodiimide, such as dicyclohexylcarbodiimide, the hydrochloride of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and the like,

In addition, the interaction may be carried out in the presence of 4-(dimethylamino)pyridine.

The amount of compound (3) is usually from 0.7 to 1.5 moles, and the amount of the condensing agent is usually from 1 to 5 Mols per 1 mol of compound (2). The amount of 4-(dimethylamino)pyridine is usually from 0.01 to 1 mole, if necessary, per 1 mol of compound (2)./p>

Temperature interaction is usually from 0 to 150°C, and interaction time is usually from 1 to 72 hours.

After the interaction, the present compound can be isolated by conventional subsequent processing of the reaction mixture, such as adding the reaction mixture to water, extracting with an organic solvent and concentrating the organic layer. If necessary, selected the present compound can be purified in such a way as chromatography, etc.

The compound (2) described in US 3466304 and can be obtained, for example, by the method described in US 3466304.

The compound (3) described in Japanese patent publication after examination S42-7906B and can be obtained, for example, by the following method.

The compound (3) can be obtained by reacting 2,2-dimethyl-3-formyltetrahydrofolate acid represented by the formula (4) (hereinafter called “compound (4)”), from methyl 2-cyanoacetate represented by the formula (5) (hereinafter called “compound (5)”), in a solvent.

Used when interacting solvent includes, for example, aliphatic hydrocarbons such as hexane, heptane, octane, Noonan and the like; aromatic hydrocarbons such as toluene, xylene, mesitylene and the like; halogenated hydrocarbons, such as 1,2-dichloroethane, chlorobenzene, dichlorobenzene, benzotrifluoride and the like; ethers such as diisopropyl ether, 1,4-dioxane and the like; alcohols such as methanol, ethanol and the like; and a mixture thereof.

Communication is usually carried out in the presence of a catalyst. The catalyst includes, for example, salts of organic acids such as ammonium acetate and the like; organic bases, such as piperidine, piperazine, morpholine, pyridine, triethylamine, etc.

The amount of compound (5) is usually from 1.0 to 1.5 moles, and the amount of catalyst is from 0.05 to 1 mol per 1 mol of compound (4).

Temperature interaction is usually from 50 to 150°C., and interaction time is usually from 0.5 to 10 hours.

The interaction is preferably carried out by removing the water formed during the interaction in the conditions of azeotropic dehydration.

After the interaction of the compound (3) can be selected in the usual further processing of the reaction mixture, such as adding the reaction mixture to water, extracting with an organic solvent and concentration of the organic layer. If necessary, compound (3) can be purified in such a way as recrystallization, etc.

The method of obtaining 2

where X represents a halogen atom such as chlorine atom and the volume of bromine.

The present compound can be obtained by reacting compound (2) with halogen 2,2-dimethyl-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylic acid represented by the formula (6) (hereinafter called “compound (6)”).

Communication is usually carried out in a solvent in the presence of a base. Used when interacting solvent includes, for example, aliphatic hydrocarbons such as hexane, heptane, octane, Noonan and the like; aromatic hydrocarbons such as toluene, xylene, mesitylene and the like; halogenated hydrocarbons such as 1,2-dichloroethane, chlorobenzene, dichlorobenzene, benzotrifluoride and the like; ethers such as diisopropyl ether, 1,4-dioxane, tetrahydrofuran, etilenglikolevye ether, diethylethylenediamine ether and the like; and a mixture thereof.

The base used in the interaction includes, for example, an organic base such as triethylamine, pyridine, N,N-diethylaniline, 4-(dimethylamino)pyridine, diisopropylethylamine etc.

The amount of compound (6) is usually from 0.7 to 1.5 moles, and the amount of the base is usually from 1 to 5 Mols per 1 mol of compound (2).

Temperature interaction is usually -20 to 100°C, and interaction time is usually from 1 to 72 hours.

After the interaction the present connection is out can be selected in the usual further processing of the reaction mixture, such as adding the reaction mixture to water, extracting with an organic solvent and concentration of the organic layer. If necessary, selected the present compound can be purified in such a way as chromatography, etc.

Examples of pests affected by this connection include arthropods such as insects and mites. Typical examples below.

Lepidoptera:

Pyralidae such asChilo suppresalis(grinder rice stalk),Cnaphalocrocis medinalis(pest, causing twisting of leaves of rice) andPlodia interpunctella(Indian meal moth); Noctuidae, such asSpodoptera litura(tobacco caterpillar),Pseudaletia separata(rice military caterpillars) andMamestera brassicae(cabbage military caterpillars); Pieridae such asPieris rapae crucivora(regular cabbage caterpillar); Tortricidae such asAdoxophyes spp.; Carosinidae; Review; Lymantriidae; Plusiinae;Agrotis spp., such asAgrotis segetum(bulbous caterpillar) andAgrotis ipsilon(black caterpillar);Helicoverpa spp.;Heliotis spp.,Plutella xylostella(Diamondback moth);Parnara guttata(rice moth);Tinea transluens(a mol);Tineola bisselliella(room furniture or clothing mol), etc.;

Diptera:

Culex spp., such asCulex pipiens pallens(common mosquito) andCulextritaeniorhynchus; Aedes spp., such asAedes aegypti(the mosquito vector of yellow fever) andAedes albopictus;Anopheles spp., such asAnopheles sinnsis ; Chironomidae (mosquito dergone); Nuscidae, such asMusca domestica(room fly),Muscina stabulans(house flies, false gigalo) andFannia canicularis(small room fly); Calliphoridae; Sarcophagidae; Anthomyiidae such asDelia platura(grain legless larva) andDelia antiqua(onion legless larva); Tephritidae (fruit flies); Drosophilidae; Psychodidae (pea flies); Phoridae; Tabanidae; Simuliidae (black flies); Stomoxyidae; Ceratopogonidae (biting mosquitoes dergone) etc.;

Dictyoptera:

Blatella germanica(cockroach-Prusak),Periplaneta fuliginosa(smoky-brown cockroach),Periplaneta americana(American cockroach),Periplaneta brunnea(brown cockroach),Blatta orientalis(Oriental cockroach), etc.;

Hymenoptera:

Formicidae (ants); Vespidae (hornets); Bethylidae; Tenthredinidae (sawflies), such asAthalia rosae ruficornis(cabbage Sawfly), etc.;

Siphonaptera:

Ctenocephalides canis(dog flea),Ctenocephalides felis(the cat flea),Pulex irritans(human flea), etc.;

Anoplura:

Pediculus humanus(a human louse),Pthiruspubis (the pubic louse),Pediculus capitis(the head louse),Pediculus corporisetc.;

Isoptera:

Reticulitermes speratus; Coptotermes formosanusetc.;

Hemiptera:

Delphacidae (delphacidae), such asLaodelphas striatellus(small brown delphacidae),Nilaparvatalugans(brown delphacidae) andSogatella furcifere(rice delacey with white back); cycatki, such asNephotettix cincticeps, Nephotettixvirescens; Aphididae (aphids R is scitella); Heteroptera(plant bugs); Aleyrodidae (white flies); scale insects; Tingidae (lace bugs); Psyllidae etc.;

Coleoptera (beetles):

Attagenus unicolor japonicus(black carpet beetle) andAuthrenus verbasci(different carpet beetles); larvae, damaging the grass roots, such asDiabrotica virgifera(Western larva damaging the grass roots) andDiabroticaundecimpunctata howardi(South larva damaging the roots of cereals); Scarabaeidae, such asAnomala cuprea (cuprous beetle) andAnomala rufocuprea(soybean beetle);Curculionidae(weevils), such asSitophilus zeamais(maize weevil),Lissorhoptrus oryzophilus(weevils that live in the rice water), round weevil andCallosobruchus chinensis(weevil bean paste); Tenebrionidae (bugs that live in darkness), such asTenebrio molitor(yellow meal worm) andTribolium castaneum(red flour beetle); Chrysomelidae (leaf beetles), such asOulema oryzae(rice leaf),Phyllotreta striolata(striped ground blaska) andAulacophora femoralis(pumpkin beetle-leaf); Anobiidae;Epilachna spp., such asEpilachna vigintioctopunctata(ladybug with twenty-eight spots); Lyctidae (flour beetles); Bostrychidae (false flour beetles); Cerambycidae;Paederusfuscipes(negligent bug), etc.;

Thysanoptera:

Thrips palmi, Flankliniella occidentalis(Western flower thrips),Thrips hawaiiensis(flower thrips), etc.;

Orthoptera:

Gryllotalpidae (mole crickets); Acrididae (grasshoppers), etc.;

Acarina:

Dermanissidae, such asDermatophagoides farinae(American home dust mite) andDermatophagoides pteronyssinus; Acaridae such asTyrophagus putrescentiae(tin mite) andAleuroglyphus ovatus(korichnevenky grain mite); Glycyphagidae such asGlycyphagus privatus,Glycyphagus domesticusandGlycyphagus destructor(grocery mite); Cheyletidae such asChelacaropsis malaccensisandCheyletus fortis; Tarsonemidae,Chortoglyphus spp.;Haplochthonius spp.; Tetranichidae, such asTetranychusurticae(red clasic with two spots),Tetranychus kanzawai(red clasic Kanzawa),Panonychus citri(citrus red mite) andPanonychus ulmi(European red mite); Ixodidae such asHaemaphysalis longiconisetc.

The pesticide composition according to the present invention, obtained in the usual way, includes the present compound and an inert carrier.

Examples of compositions include oil solutions, emulsifiable concentrates, wettable powders, flowable formulations (e.g., aqueous suspension, aqueous emulsion), powders, granules, aerosols, volatile compounds for heating (for example, a spiral from mosquitoes, liners for electric heater, liquid for electric heater), heating fumigants (e.g. incinerated fumigant, chemical fumigant, porous ceramic fumigant), ringrevenue volatile composition (e.g., volatile resin composition impregnated paper volatile compounds), Smoking compositions (the example forming fog), composition ULV (ultra low volume) and poisoned bait.

Can be, for example, used the following methods of obtaining compositions.

(1) Mixing the present compound with a solid carrier, liquid carrier, gaseous carrier, bait or the like, optionally adding excipients for the compositions, such as surfactants and the like, and the preparation of a mixture.

(2) the Impregnation of the base material, containing no active ingredients, a real connection.

(3) Mixing the present compound with the substrate material and the preparation of a mixture.

The contents of this connection in the pesticide composition according to the present invention depends on the type of compositions, however, such compositions typically contain from about 0.001 to 95% by weight. of this connection.

Examples of the medium used to obtain the compositions include solid carriers such as clays (e.g. kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, clay fubasami, acid clay), talc and the like, ceramics, other inorganic minerals (e.g. sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, montmorillonite) and chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, nitrate Ammon is I, urea, ammonium chloride); liquid carriers such as water, alcohols (e.g. methanol, ethanol), ketones (e.g. acetone, methyl ethyl ketone), aromatic hydrocarbons (e.g. benzene, toluene, xylene, ethylbenzene, methylnaphthalene, phenylxylylethane), aliphatic hydrocarbons (e.g. hexane, cyclohexane, kerosene, gas oil), esters (ethyl acetate, butyl acetate), NITRILES (e.g. acetonitrile, isobutyronitrile), ethers (e.g. diisopropyl ether, dioxane), acid amides (e.g. N,N-dimethylformamide, N,N-dimethylacetamide), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, dimethyl sulfoxide, vegetable oils (e.g. soybean oil, cotton oil); and gaseous media, such as gaseous Flon, gaseous butane, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.

Examples of surfactants include alkyl sulphates, salts of alkyl sulphonates, salts of alkylarylsulfonates, ethers of alkylaryl, ethers polyoxyethylenated aryl, ethers of polyethylene glycol, esters of polyhydric alcohols and derivatives, sugar alcohols.

Examples of other excipients used in these compositions include adhesive agents, dispersing agents and stabilizers, as a rule, casein, gelatin, polysaccharides (EmOC is emer, starch, gum Arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone), polyacrylic acid, BHT (2,6-di-tert-butyl-4-METHYLPHENOL) and BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

The base material for the spiral from mosquitoes, for example, is a mixture of raw vegetable powder such as wood powder and husk of the fruit Pyrethrum, and a bonding agent, such as Tabu powder (powder of Machilus thunbergii), starch or gluten.

The base material of the liner from mosquitoes for electric heating is, for example, the plate consists of fibrils of cotton fluff or a mixture of pulp and fluff of cotton.

The base material combustion fumigant includes, for example, exothermic agents (e.g., nitrates, nitrites, guanidine salt, potassium chlorate, nitrocellulose, ethylcellulose, wood powder), pyrolytic stimulating agents (such as salts of alkali metals, salts of alkaline earth metals, dichromate and chromates), oxygen (e.g., potassium nitrate), substances that contribute to combustion (e.g., melanin, wheat starch), volumetric fillers (for example, kieselguhr) and a binding agent (for example, synthetic glue).

The mother of the l basis for chemical fumigant includes, for example, exothermic agents (for example, sulfides, alkali metal polysulfides, servocity, calcium oxide), catalytic agents (for example, the carbonaceous substances, iron carbide and activated clay), organic foaming agents (for example, azodicarbonamide, benzosulfimide, dinitrosopentamethylenetetramine, polystyrene, polyurethane) and fillers (for example, natural or synthetic fibers).

The base material ringrevenue volatile composition includes, for example, thermoplastic resin and paper (for example, filter paper, Japanese paper).

The base material poisonous bait includes components for lures (for example, the powder grains, vegetable oil, sugar, crystalline cellulose), antioxidants (for example, dibutylaminoethanol, nordihydroguaiaretic acid), preservatives (for example, dehydroacetic acid), substances for preventing erroneous consumption by children and Pets (for example, powder of red pepper), flavourings, attracting pests (for example, the flavor of the cheese, the aroma of onions, peanut butter).

Method of pest control according to the present invention is generally carried out applying the pesticide composition according to the present invention on the pests or their habitat.

Methods of application pesticide HDMI is tion according to the present invention, for example, below. How appropriately chosen depending on the type of pesticide composition or application.

(1) a Method of applying a pesticide composition according to the present invention as such on the pests or their habitat.

(2) Method of diluting the pesticide composition according to the present invention a diluent, such as water, and then applying to the pests or their habitat.

In this case, the pesticide composition according to the present invention, obtained in the form of emulsifiable concentrates, wettable powders, flowable formulations, compositions in the form of microcapsules, etc., diluted to the concentration of this compound constituting from 0.1 to 10000 ppm

(3) Method of evaporation of the active ingredient at ordinary temperature or by heating the pesticide composition according to the present invention in the habitat of pests.

In such cases, the dosage of the present compounds are selected in accordance with the form of the pesticide composition according to the present invention, the time, place, and method of its application, the type of pests, damage, etc. However, the amount of the present compound is usually from 1 to 10000 mg/m2when applied on the surface or from 0.1 to 5000 mg/m3surround use.

The pesticide composition according to the ACLs of the present invention can be used simultaneously with another insecticide, nematocidal, agent for controlling soil pests, fungicide, herbicide, plant growth regulator, a repellent, a synergist, fertilizer or conditioning the soil in pre-mixed or unmixed form.

Examples of active ingredients of insecticides and acaricide include organophosphorus compounds such as fenitrothion, fenthion, diazinon, chlorpyrifos, Arafat, mitigation, DDVP, sulprofos, cyanophos, dioxybenzone, dimethoat, pentat, Malathion, trichlorfon, azinphosmethyl, monocrotophos, ation; carbamate compounds such as VRMS, benfuracarb, propoxur, carbosulfan, carbaryl, methomyl, ethiofencarb, aldicarb, oxamyl and fanatical; PYRETHROID compounds such as etofenprox, fenvalerate, esfenvalerate, fenpropathrin, cypermethrin, permethrin, cigalotrin, deltamethrin, cicloprofen, fluvalinate, bifenthrin, 2-methyl-2-(4-bromodifluoromethyl)propyl 3-phenoxybenzyl ether, tralomethrin, selflove, d-phenothrin, cyphenothrin, Dr. resmethrin, acrinathrin, cyfluthrin, transfluthrin, tetramethrin, allethrin, prallethrin, empenthrin, imiprothrin, Dr. permethrin and 5-(2-PROPYNYL)furfuryl 2,2,3,3-tetramethylcyclopropanecarboxylate; derivatives of nitroimidazolidin; derivatives of N-cyanoaniline, such as acetamiprid; chlorinated hydrocarbons such as endosulfan, g-ANS and 1,1-bis(chlorophenyl)-2,2,2-trichloro anal; connection benzoylferrocene, such as chlorfluazuron, teflubenzuron and flufenoxuron; connection phenylpyrazole; methoxamine; bromopropylate; tetradifon; chinomethionat; pyridaben; fenpyroximate; diafenthiuron; tebufenpyrad; complex polination, such as tetradactyl, dynactin and tinactin; milbemectin; abamectin; ivermectin; and azadirachtin.

Examples of the active ingredient repellent include 3,4-carandol, N,N-diethyl-m-toluamide, 1-methylpropyl 2-(2-hydroxyethyl)-1-piperidinecarboxylate, p-Menten-3,8-diol, Botanical essential oils (for example, oil of hyssop).

Examples of the active ingredient and synergist include simple ether bis(2,3,3,3-tetrafluoropropyl) (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboximide (MGK-264) and 5-[2-(2-butoxyethoxy)ethoxymethyl]-6-propyl-1,3-benzodioxol(piperonyl piperonyl).

Examples

The present invention is illustrated with sample receipt, sample composition, sample testing etc, while the present invention is not limited to the given examples.

First of all, the following is an example of getting this connection.

Example get

In a 50 ml round-bottom flask of 0.67 g of 5-benzyl-3-furylmethanol, 0,79 g 1R-TRANS-2,2-dimethyl-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylic acid, of 0.13 g of 4-(dimethylamino)pyridine, 10 ml methylenchlorid the and and at room temperature add 0,80 g dicyclohexylcarbodiimide. The mixture is stirred at room temperature for 3 hours. The reaction mixture was subjected to vacuum filtration through a glass filter and the residue washed with 40 ml of a simple diethyl ether. The filtrate are combined and concentrated under reduced pressure. The obtained oily raw product is subjected to column chromatography on silica gel, receiving of 0.59 g of 5-benzyl-3-furylmethyl 1R-TRANS-2,2-dimethyl-3-((E)-2-cyano-3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate (hereinafter referred to as the present compound (1)”) with the release of 42%.

1H-NMR (CDCl3, TMS) d (ppm): 1,30 (s, 3H), 1,32 (s, 3H), 2,10 (d, 1H), 2,64 (DD, 1H), 3,84 (s, 3H), 3,93 (s, 2H), 4,94 (kV, 2H), 6,04 (s, 1H), 7,21-7,39 (m, 7H).

Examples of compositions are given below. Part (s) means the weight fraction (weight part).

Example compositions 1

Twenty parts of the present compounds (1) are dissolved in 65 parts of xylene. To add fifteen parts Sorpol H (registered trademark Toho Chemical), mix and mix well, getting emulsifiable concentrate.

Example composition 2

Five parts of Sorpol H added to 40 parts of the present compounds (1) and mix well. To add thirty-two parts of Carplex #80 (synthetic hydrated silica, registered trademark Shionogi & Co.) and 23 parts of 300-mesh diatomaceous earth and well peremeshivayu mixer for juice, getting a wettable powder.

An example of the composition 3

A mixture of 10 parts of the present compounds (1), 10 parts of phenylxylylethane and 0.5 part of Sumidur L-75 (tolylenediisocyanate, manufactured by Sumika Bayer Urethane Co., Ltd.) added to 20 parts of a 10% aqueous solution of gum Arabic and stirred homogeneous mixer, receiving the emulsion having the average particle diameter of 20 μm. To it was added two parts of ethylene glycol and stirred for 24 hours in a water bath with a temperature of 60°C., obtaining the suspension of microcapsules. The solution of the thickener get dispersive 0.2 part of xanthan resin and 1.0 part Beagum R (silicate of aluminum, magnesium, manufactured by Sanyo Chemical Co., Ltd.) in 56,3 parts of ion exchange water. Forty-two and a half (42,5) part of the above suspension of microcapsules and 57.5 parts of the above solution of the thickener is mixed, receiving microencapsulated composition.

An example of the composition 4

A mixture of 10 parts of the present compounds (1) and 10 parts of phenylxylylethane added to 20 parts of a 10% aqueous solution of polyethylene glycol and stirred homogeneous mixer, receiving the emulsion having the average particle diameter of 3 μm. The solution of the thickener get dispersive 0.2 part of xanthan resin and 1.0 part Beagum R (silicate of aluminum, magnesium, manufactured by Sanyo Chemical Co., Ltd.) in 58,8 parts of ion exchange water. Forty parts of the above emulsion and 60 parts of the above-mentioned RA is down thickener is mixed, receiving fluid composition.

An example of the composition 5

Five parts of the present compound (1) is mixed with three parts of Carplex #80 (fine powder of synthetic hydrated silica, trademark Shionogi & Co.), of 0.3 parts of PAP (a mixture of monoisopropylamine and Diisopropylamine) and 91,7 parts of 300-mesh diatomaceous earth and mixed in the mixer for juice, getting dust.

An example of the composition 6

One-tenth (0.1) part of the present compounds (1) are dissolved in 5 parts of dichloromethane and mixed with 94,9 parts of deodorized kerosene, getting oil solution.

An example of the composition 7

The aerosol container filled with a solution obtained by dissolving 1 part of the present compounds (1) with 5 parts of dichloromethane and mixed with 34 parts of deodorized kerosene. The balloon is then provided with a valve and through him in the aerosol container under pressure load 60 parts of a propellant (liquefied petroleum gas), receiving the aerosol oil-based.

An example of the composition 8

The aerosol container is filled with 50 parts of water and a mixture of 0.6 parts of the present compounds (1), 5 parts of xylene, and 3.4 parts of deodorized kerosene and 1 part of Atmos 300 (emulsifier, a trademark of Atlas Chemical Co.). The balloon is then provided with a valve and through him in the aerosol container under pressure load 40 parts of a propellant (liquefied Neftegaz), receiving an aerosol water-based.

An example of the composition 9

The solution obtained by dissolving 0.3 g of the present compound (1) in 20 ml of acetone, homogeneous mixed with 99,7 g media for spiral from mosquitoes (a mixture of Tabu powder, fruit pomace Pyrethrum and wood powder in a ratio of 4:3:3). Then add 100 ml of water, the mixture is well mixed, molded and dried, obtaining a spiral from mosquitoes.

An example of the composition 10

Ten milliliters (10 ml) solution get by dissolving 0.8 g of the present compound (1) and 0.4 g of piperonylbutoxide in acetone. 0.5 ml of the resulting solution is homogeneous impregnorium the base material (plate consists of fibrils of a mixture of pulp and fluff of cotton: of a thickness of 2.5 cm × 1.5 cm × 0.3 cm), receiving a plaque from mosquitoes.

An example of the composition 11

Three parts of the present compound (1) dissolved in 97 parts of deodorized kerosene. The resulting solution was loaded into the cylinder of PVC. In the container insert of porous absorbent wick of the inorganic powder of the cured binder, and then calcined, the upper part of which may be heated by the heater receiving part heated by electricity fumigator.

An example of the composition 12

A solution obtained by dissolving 100 mg of the present compound (1) in an appropriate amount of acetone, impregnorium porous KERS is ical plate (thickness of 4.0 cm × 4.0 cm × 1.2 cm), receiving a fumigant for heating.

An example of the composition 13

The solution obtained by dissolving 100 mg of the present compound (1) in an appropriate amount of acetone, applied on filter paper (thickness 2.0 cm × 2.0 cm × 0.3 mm) and the acetone is evaporated, getting a volatile agent used at room temperature.

An example of the composition 14

Filter paper impregnorium the acetone solution of this compound (1) so that the amount of the present compounds was 1 g per 1 m2and the acetone was evaporated, providing protection from ticks.

The following example test shows that this connection can be used as the active ingredient of the pesticide composition.

Example test 1

A solution of 0.025 part of the present compound (1)dissolved in 10 parts of dichloromethane, mixed with 89,975 parts of deodorized kerosene, getting 0,025% oil solution.

Ten females of the ordinary mosquito (Culex pipiens pallens) is placed in a cubic chamber (the length of the side face 70 cm). Seven-tenths (0,7) ml of 0.025% oil solution of the present compound (1) is sprayed using a spray pressure of 8.8 × 104PA from a small window in the side of the camera. Then count the number of affected insects with an interval of 10 minutes. On the basis of the received who's results determine time (CT 50)needed to defeat half of the tested insects.

For comparison, 5-benzyl-3-furylmethyl 1R-TRANS-2,2-dimethyl-3-((E)-2-cyano-3-ethoxy-3-oxo-1-propenyl)cyclopropanecarboxylate (hereinafter referred to as comparative compound”) is also subjected to the above test. One connection tested twice. The results are presented in the table.

CT (min)
The present compound (1)0,7
Comparative compound6,1

Industrial applicability

This connection can be used for effective control of pests such as insects, etc.

1. Ester compound of formula (1)

2. Ester compound according to claim 1, in which the substituent in position 1 cyclopropanol ring and the substituent in position 3 cyclopropanol rings are transconfiguration.

3. The pesticide composition comprising the ester compound according to claim 1 as an active ingredient and an inert carrier.

4. A method of combating pests comprising applying an effective amount of the ester compound according to claim 1 at a time is Italy or the place they live.

5. The use of the ester compound according to claim 1 as an active ingredient of the pesticide composition.



 

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FIELD: agriculture.

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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.

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5 cl, 1 tbl, 16 ex

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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:

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