ITTO20070225A1 - 1,3-BENZODIOSSOL COMPOUND AND ITS USE - Google Patents

Description

DESCRIPTION

"Compound 1,3-benzodioxole and its use",

DESCRIPTION FIELD OF THE INVENTION

The present invention relates to the 1,3-benzodioxole compound and its use.

BACKGROUND OF THE INVENTION

In Journal of the Chemical Society of Japan, Vol. 79, No. 12, page 1554 to 1556 (December 1958), a compound is described which enhances the insect control effect of pesticide compositions.

SUMMARY OF THE INVENTION

The present inventors have studied to find a compound having a pest control effect enhancing effect of a pesticidal composition, in which the compound is contained together with an active ingredient such as a pestipresent compound and an active ingredient such as a pesticide;

[7] the pesticidal composition according to [6], wherein the active ingredient as a pesticide is a pyrethroid compound;

[8] a method of controlling a pest by applying an effective amount of the present compound and an active ingredient as a pesticide to a pest or a biotope thereof;

[9] the method of controlling a pest according to [8], wherein the active ingredient as a pesticide is a pyrethroid compound; And

[10] The use of the present compound to control a pest by simultaneous application to a pest or a biotope thereof of an active ingredient as a pesticide.

WAY TO CARRY OUT THE INVENTION

In the present invention, examples of the C3 alkyl group represented by R1 comprise a propyl group, and examples of the C3 alkenyl group comprise a 2-propenyl group.

In the present invention, examples of C 1-3 alkyl group represented by R2 include a methyl group, an ethyl group and a propyl group.

cida, have found that a 1,3-benzodioxole compound represented by the following Formula (I) has such an effect, and have obtained the present invention.

Hence, the present invention has the following aspects [1] to [10]:

[1] a 1,3-benzodioxole compound represented by Formula (I) (hereinafter may be referred to as the present compound):

wherein R1 represents a C3 alkyl group or a C3 alkenyl group, and R2 represents a C3-3 alkyl group;

[2] the 1,3-benzodioxole compound according to [1], wherein R1 is a propyl group or a 2-propenyl group;

[3] the 1,3-benzodioxole compound according to [1] or [2], wherein R2 is a methyl group.

[4] The 1,3-benzodioxole compound according to [1] or [2], wherein R2 is an ethyl group.

[5] The 1,3-benzodioxole compound according to [1] or [2], wherein R2 is a propyl group.

[6] A pesticidal composition comprising the present compound, for example, can be produced by the following processes.

Production process 1

The present compound can be produced, for example, by reacting compound (II) with compound (III):

(where R <1> and R <2> have the same meaning as above, and X <1> represents a halogen atom).

The reaction is carried out in the presence of a base, and usually in the presence of a solvent.

The solvent used for the reaction includes, for example, aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as benzene and tolue-ne; ethers such as diethyl ether, tert-butylmethylether, tetrahydrofuran and 1,4-dioxane; acid amides such as N, N-dimethylformamide; sulfoxides such as dimethyl sulfoxide; and water and a mixture thereof.

The base used for the reaction includes, for example, alkali metal hydrides such as potassium hydride and sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; and alkali metal carbonates such as potassium carbonate and sodium carbonate. The base is typically used in a ratio of 1 to 5 moles to 1 mol of compound (II).

The reaction can also be carried out in the co-presence of alkali metal halide. The alkali metal halide includes, for example, potassium iodide. When there is co-presence of alkali metal halide, it is typically used in a ratio of 1 to 5 moles per 1 mol of compound (II).

Compound (III) is used in the reaction typically in a ratio of 1 to 5 moles to 1 mol of compound (II).

The reaction temperature is normally in the range of 0 to 150 ° C, and the reaction time is normally in the range of 1 to 24 hours.

After completion of the reaction, the present compound can be isolated by post-treating it, such as adding the reaction mixture in water, extracting with an organic solvent, and then drying and concentrating the organic layer. The present isolated compound can be further purified by chromatography and the like.

Production process 2

Compound (I-1) of the present invention can also be produced by reducing compound (1-2):

wherein R <2> has the same meaning as above, and R <1_1> represents an allyl group.

The reaction is carried out in the presence of hydrogen gas and a reduction catalyst, and normally in the presence of a solvent.

The solvent used for the reaction includes, for example, aliphatic hydrocarbons such as hexane and heptane; alcohols such as methanol and ethanol; esters such as ethyl acetate; and water and a mixture thereof.

The reduction catalyst used for the reaction includes, for example, palladium carbon and platinum oxide. The reduction catalyst is typically used in a ratio of 0.05 to 0.5 moles per 1 mol of the compound (1-2).

The reaction temperature is normally in the range from 0 to 80 ° C, in which the end of the reaction can be confirmed by consuming the amount of hydrogen gas theoretically necessary for the reduction, and the reaction time is normally in the range from 1 to 48 hours.

After completion of the reaction, the compound (1-1) can be isolated by subjecting it to post-treatment as filtration of the reaction mixture, and then concentrating the filtrate obtained. The isolated compound (I-1) can be further purified by chromatography and the like.

Production process 3

The present compound can be produced by reacting compound (IV) with compound (V):

wherein R1 and R2 have the same aforementioned meaning, and X2 represents a halogen atom.

The reaction is carried out in the presence of a base, and usually in the presence of a solvent.

The solvent used for the reaction includes, for example, aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, tert-butylmethylether, tetrahydrofuran and 1,4-dioxane; acid amides such as N, N-dimethylformamide; and sulfoxides such as dimethyl sulfoxide.

The base used for the reaction includes, for example, alkali metal hydrides such as potassium hydride and sodium hydride. The base is typically used in a ratio of 1 to 5 moles to 1 mol of the compound (IV).

Compound (V) is used for the reaction typically in a ratio of 1 to 5 moles to 1 mol of compound (IV).

The reaction temperature of the reaction is normally in the range of 0 to 150 ° C, and the reaction time is normally in the range of 1 to 24 hours.

After completion of the reaction, the present compound can be isolated by post-treating it as adding the reaction mixture in water, extracting with an organic solvent, and then drying and concentrating the organic layer. The present isolated compound can be further purified by chromatography and the like. Reference production process

Compound (IV) can be produced by reacting compound (II) with compound (VI):

where R1 has the same meaning as above, and X3 represents a halogen atom.

The reaction is carried out in the presence of a base, and usually in the presence of a solvent.

The solvent used for the reaction includes, for example, aliphatic hydrocarbons such as hexane and heptane; aromatic hydrocarbons such as benzene and toluene; ethers such as diethyl ether, tert-butylmethylether, tetrahydrofuran and 1,4-dioxane; acid amides such as N, N-dimethylformamide; and sulfoxides such as dimethyl sulfoxide.

The base used for the reaction includes, for example, alkali metal hydrides such as potassium hydride and sodium hydride. The base is typically used in a ratio of 1 to 5 moles to 1 mol of compound (II).

Compound (VI) is used in the reaction typically in a ratio of 1 to 5 moles to 1 mol of compound (II).

The reaction temperature is normally in the range of 0 to 150 ° C, and the reaction time is normally in the range of 1 to 24 hours.

After completion of the reaction, compound (IV) can be isolated by post-treating it as adding the reaction mixture in water, extracting with an organic solvent, and then drying and concentrating the organic layer. The isolated compound (IV) can be further purified by chromatography and the like.

The pesticidal composition of the present invention comprises the present compound and an active ingredient as a pesticide (hereinafter the present compound and the active ingredient as a pesticide being referred to globally as the present active ingredient). The ratio of the present compound to the active ingredient as a pesticide which are contained in the pesticide composition of the present invention is optionally adjustable without limitation depending on the control purposes such as types of pests, places for application, times of application, types of active ingredient as a pesticide, the typical weight ratio (present compound: active ingredient as pesticide) being from about 1: 100 to about 100: 1, preferably from about 1:50 to about 50: 1, more preferably from 20: 1 at 1: 1.

Examples of the active ingredient as a pesticide containing the pesticidal composition of the present invention together with the present compound include the following:

pyrethroid compounds such as allethrin, tetramethrin, prallethrin, phenothrin, resmethrin, cyphenothrin, permethrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, tralomethrin, cyfluthrin, beta-cyf luthrin, cyhalothrin, etofipenrxrothrin fenvalerate, esfenvalerate, fenpropathrin, silafluofen, bifenthrin, transfluthrin, flucythrinate tau-fluvalinate, acrinathrin, tefluthrin, cycloprothrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) -benzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-lenylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl -3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl- (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methylprop-1 -enyl) cyclopropanecarboxylate, empenthrin, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -3- (2-cyano-propenyl) -2,2-dimethylcyclopropanecarboxylate , 2,3, -5.6-tetrafluoro-4-methoxymethylbenzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -3- ( 2-cyano-2-ethoxycarbonylvinyl) -2,2-dimethylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl- (1RS, 3RS; 1RS, 3SR) -3- (2,2-dichlorovinyl) -2 , 2-dimethylcyclopropanecarboxylate, 2.3.5.6-tetrafluoro-4-methoxymethylbenzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -3-methoxyiminomethyl-2, 2-dimethylcyclopropanecarboxylate and 2,3,5,6-tetrafluoro-4 -methoxymethylbenzyl- (EZ) - (1RS, 3RS; 1RS, 3SR) -3- (2-ethoxycarbonyl-2-fluorovinyl) -2,2-dimethylcyclopropanecarboxylate;

organic phosphorus compounds such as dichlorvos, fenitrothion, cyanophos, profenofos, sulprofos, phenthoate, isoxation, tetrachlorvinphos, fenthion, chlorpyriphos, diazinon, acephate, terbufos, phorate, chlorethoxyfos, fosthiazate, etusaidhoprophos;

carbamate compounds such as propoxur, carbaryl, metoxadiazone, phenobucarb, methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb and methiocarb;

benzoylphenylurea compounds such as lufenuron, chlorfluazuron, hexaflumuron, diflubenzuron, triflumuron, teflubenzuron, flufenoxuron, fluazuron, novaluron, triazuron and bistrifluron;

juvenile hormone-like substances such as pyriproxyfen, methoprene, hydroprene and fenoxycarb; neonicotinoid compounds such as acetamiprid, nitenpyram, thiacloprid, thiamethoxam, dinotefuran, imidacloprid and clothianidin;

phenylpyrazole compounds such as acetoprol and etiprole;

benzoylhydrazine compounds such as tebufenozide, chromafenozide, methoxyphenozide and halophenozide;

other active ingredients such as pesticides such as diafenthiuron, pymetrozine, flonicamid, triazamate, buprofezin, spinosad, emamectin benzoate, chlorfenapyr, indoxacarb MP, pyridalyl, cyromazine, fenpyroximate, tebufenpyrad, tolfenpyrad, pyridabin, pyridifenpyrad, tolfenpyrad, pyridifen clofentezine, fenbutatin oxide, dicofol, propargite, abamectin, milbemectin, amitraz, cartap, bensultap, thiocyclam, endosulfan, spirodiclofen, spiromesifen, amidoflumet and azadirachtin.

One or two or more types of these active ingredients as pesticides can be used for the pesticide composition of the present invention.

Although the pesticidal composition of the present invention may be the present active ingredient itself, it is normally formulated into a preparation by mixing with a solid carrier, a liquid carrier and / or a gaseous carrier and further, if necessary, by adding a surfactant and others. adjuvants for the formulation. Therefore, the pesticidal composition of the present invention normally contains the present active ingredient and further contains an inert carrier. Such a preparation includes, for example, an emulsion, a solution in oil, a shampoo preparation, a flowable preparation, a powder, a wettable powder, a granule, a paste, a microcapsule, a foam, an aerosol, a preparation with gaseous carbon dioxide, a tablet, a resin preparation, a paper preparation, a non-woven fabric preparation and a knitted or woven fabric preparation. These preparations can be used in the form of poisonous bait, pesticide coil, electric pesticide plate, smoke preparation, fumigant or foil.

A preparation of the pesticidal composition according to the present invention normally contains from 0.01 to 98% by weight of the present active ingredient.

A solid carrier used for the formulation includes finely divided powder or clay granules (e.g. kaolin clay, diatomaceous earth, bentonite, Fubasami clay, acid clay, etc.), synthetic hydrated silicon oxide, talc, ceramics, other minerals inorganic (e.g. sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica, etc.) or chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea, etc.) ; a substance which can be sublimated and is in solid form at normal temperature (for example 2,4,6-triisopropyl-1, 3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, adamantane, etc.); wool; silk; cotton; hemp; pulp; synthetic resins (e.g. polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymers and ethylene-ethyl methacrylate copolymers; ethylene-acrylic acid esters copolymers such as ethylene-methyl acrylate copolymers and ethylene ethyl acrylate copolymers; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymers; ethylene-tetracyclododecene copolymers such as ethylene-tetracyclododecene copolymers; methylpent-1-ene, polybut-1-ene, polybutadiene, polystyrene; acrylonitrile-styrene resins; styrene elastomers such as acrylonitrile-butadiene-styrene resins, styrene-diene-conjugated block copolymers and conjugated styrene-diene block copolymer hydrides; fluororesins ; acrylic resins such as poly (methylmetacra side); polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene terephthalate, polybutylene terephthalate and polycyclohexylenedimethylene terephthalate; polycarbonates, polyacetals, polyacrylsulfones, polyarylates, polyesters of hydroxybenzoic acid, polyetherimides, polyester carbonates, polyphenylene ether resins, polyvinyl chloride, polyvinylidene chloride, polyurethane and porous resins such as expanded polyurethane, expanded polypropylene or expanded ethylene, glass, etc.) metals, ceramics, fibers, fabrics, knitted fabrics, sheets, papers, yarn, foam, porous substances and multifilaments.

A liquid carrier includes, for example, aromatic or aliphatic hydrocarbons (for example xylene, toluene, alkylnaphthalene, phenylxyl ethane, kerosene, gas oil, hexane, cyclohexane, etc.), halogenated hydrocarbons (for example chlorobenzene, dichloromethane, dichloroethane, trichloroethane, etc.). ), alcohols (for example methanol, ethanol, isopropyl alcohol, butanol, eessaannoolloo, benzyl alcohol, ethylene glycol, etc.), ethers (for example diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethylether, propylene glycol monetrahydro methyl ether, etc. .), esters (for example ethyl acetate, butyl acetate, etc.), ketones (for example acetone, methylethylketone, methylisobutylketone, cyclohexanone, etc.), nitriles (for example acetonitrile, isobutyronitrile, etc.), sulfoxides (for e.g. dimethylsulfoxide, etc.), acid amides (e.g. N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, etc.), alkylidencarbonates (e.g. pious propylene carbonate, etc.), vegetable oil (e.g. soybean oil, cottonseed oil, etc.), essential vegetable oils (e.g. orange oil, hyssop oil, lemon oil, etc.), and water .

A gaseous carrier includes, for example, butane gas, flon gas, liquefied petroleum gas (LPG), dimethylether and carbon dioxide gas.

A surfactant includes, for example, alkyl sulfate ester salts, alkylsulfonates, alkylaryl sulphonates, alkylaryl ethers and their polyoxyethylenated products, polyethylene glycol ethers, esters of polyvalent alcohols and sugar alcohol derivatives.

Other formulation aids include binders, dispersants and stabilizers, specifically e.g. casein, gelatin, polysaccharides (e.g. starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, sugars, soluble synthetic polymers in water (e.g. polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid, etc.), PAP (acidic isopropylphosphate), BHT (2,6-di-t-butyl-4-methylphenol), BHA (a mixture of 2-t-butyl -4-methoxyphenol and 3-t-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.

A base material for a resin preparation includes, for example, polyethylene resins such as low density polyethylene, linear low density polyethylene and high density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymers; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymers and ethylene-ethyl methacrylate copolymers; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymers and ethylene-ethyl acrylate copolymers; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymers; ethylene-tetracyclododecene copolymers; polypropylene resins such as propylene copolymers and propylene-ethylene copolymers; poly-4-methylpent-1-ene, polybut-1-ene, polybutadiene, polystyrene, acrylonitrile-styrene resins; styrene elastomers such as acrylonitrile-butadienestyrene resins, conjugated styrene-diene copolymers and conjugated styrene-diene block copolymer hydrides; fluororesins; acrylic acid resins such as poly (methyl methacrylate); polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylenephthalate, polybutylenebutalate, and polycyclohexylenedimethylene terephthalate; polycarbonates, polyacetals, polyacryl sulfones, polyarylate, hydroxybenzoic acid polyesters, polyetherimides, polyestercarbonates, polyphenylene ether resins, polyvinyl chloride, polyvinylidene chloride and polyurethane. These base materials can be used alone or as a mixture of two or more. A plasticizer such as phthalic acid ester (e.g. dimethyl phthalate, dioctyl phthalate, etc.), adipic acid ester or stearic acid, can be added to these base materials if necessary.

The resin preparation can be achieved by mixing the present active ingredient into the base material, followed by molding such as injection molding, extrusion molding or pressing molding. The resulting resin preparation can be formed in the form of plate, film, tape, net, string or the like by a further step, if necessary, of molding, cutting or the like. These resin preparations can be used in the form of an animal collar, an animal ear tag, a sheet preparation, a wire or a horticultural stake.

A base material of a poisoned bait includes, for example, grain powder, vegetable oil, sugar and crystalline cellulose. An antioxidant such as dibutylhydroxytoluene or nordihydroguaiaretic acid, a preservative such as dehydroacetic acid, an agent to prevent accidental ingestion by children or pets such as chili powder, and a scent that attracts harmful insects such as the scent of cheese, the scent of onion or peanut oil can be added to the base material if necessary.

The present compound can be used in the control of pests by applying an effective amount of the present compound and an active ingredient as a pesticide to the pests directly and / or their biotope (e.g. plants, animals, soil, etc.).

When the pesticidal composition of the present invention is used to control pests in agriculture and forestry, the application amount is normally 1 to 100,000 g / ha, preferably 10 to 1,000 g / ha of the total amount of the present active ingredient. When the pesticidal composition of the present invention is in the form of emulsion, wettable powder, sliding agent or microcapsule, it is normally used after dilution with water so as to have a concentration of the present active ingredient from 0.01 to 1,000 ppm. When the pesticidal composition of the present invention is in the form of a solution in oil, a powder or granule is normally used as such.

These preparations can be sprayed as such to the plants to be protected against harmful insects, or they can be diluted with water and then sprayed on the plant to be protected against harmful insects. The soil can be treated with these preparations to control pests that live in the soil. Seedbeds before sowing or sowing holes or plant feet in sowing can also be treated with these preparations. Furthermore, a sheet preparation of the pesticidal composition of the present invention can be applied by wrapping it around the plants, placing it near the plants, depositing it on the surface of the soil at the feet of the plant or the like.

When the pesticidal composition of the present invention is used for the control of epidemic pests, the application amount is normally 0.001 to 100 mg / m3 as the total amount of the present active ingredient for application to space, and 0.001 to 1,000 mg / m2 as the total amount of this active ingredient for application to a plan. When the pesticidal composition of the present invention is in the form of an emulsion, wettable powder or flowable agent, it is normally applied after dilution with water so as to have a concentration of the present active ingredient from 0.001 to 100,000 ppm, preferably from 0.01 to 1,000 ppm. When the pesticidal composition of the present invention is in the form of a solution in oil, aerosol, smoke preparation or poisoned bait, it is normally applied as such. The pesticide composition in the form of a pesticide spiral, or electric pesticide plate, is applied by emitting the present active ingredient by heating according to its form. The pesticidal composition in the form of resin preparation, paper preparation, tablet, nonwoven preparation, knitted or woven preparation or sheet preparation can be applied, for example, by leaving the preparation as such in a space in to which it must be applied and sending air towards the preparation.

A space to which the pesticide composition of the present invention is applied for the prevention of epidemics includes, for example, a built-in wardrobe, a Japanese-style built-in wardrobe, a Japanese-style chest, a sideboard, a cabinet, a dining room. bathroom, a wooden environment, a living room, a dining room, a warehouse and the interior of a vehicle. The pesticide composition can also be applied in an outdoor open space.

When the pesticidal composition of the present invention is used to control parasites living outside livestock such as a cow, horse, pig, sheep, goat or chicken, or a small animal such as a dog, cat, rat or mouse, it can be used for said animal by a procedure known in the veterinary field. Specifically, when systemic control is desired, the pesticidal composition is administered, for example, as a tablet, a mixture with the feed, a suppository or an injection (for example, intramuscular, subcutaneous, intravenous, intraperitoneal, etc.). When non-systemic control is desired, a process for using the pesticidal composition of the present invention comprises spraying, spraying or spot treatment with the pesticidal composition in the form of a solution in oil or aqueous liquid, washing an animal with the pesticidal composition in form of shampoo preparation, and attachment of a collar or ear tag consisting of the pesticide composition in the form of a resin preparation, to an animal. When administered to an animal, the total amount of this active ingredient is normally in the range of 0.01 to 1,000 mg per 1 kg of body weight of the animal.

Harmful insects against which the pesticidal composition of the present invention has a control effect include harmful arthropods such as insects and mites. More specifically, their examples are listed below.

Hemiptera:

Delfacids such as Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera and the like, Deltocephalids such as Nephotettix cincticeps, Nephotettix vìrescens and the like,

Aphids such as Aphis gossypii, Myzus persìcae and the like,

Pentatomids and Alididae such as Nezara antennata, Rìptortus clavetus, Eysarcorìs lewìsì, Eysarcorìs parvus, Plautia stali, Halyomorpha mista and the like, Aleirodids like Trialeurodes vaporariorum, Bemisia argenti folli and the like,

Diaspids, Coccidia and Margarodids such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis ci -tri, Ceroplastes rubens, Icerya coersi and similar, Tingidi,

Bedbugs such as Cimex lectularius and similar Psylids and the like;

Lepidoptera:

Pyralids such as Chilo suppressalis, Cnaphalocrocis medinalis, Notarcha derogata, Piodia interpunctella and the like,

Noctuids such as Spodoptera litura, Pseudaletia separated, Trichoplusia spp. , Heliothis spp. , Heli -coverpa spp. and similar ,

Pierids such as Pieris rapae and similar, Tortricides such as Adoxophyes spp. , Grapholita molesta, Cydia pomonella and the like,

Carposinids such as Carposina niponensis and the like,

Lionetidae such as Lyonetia spp. and the like, Limantridae such as Lymantria spp., Euproctis spp. and similar,

Hyponomeutidae such as Plutella xylostella and the like,

Gelechids such as Pectinophora gossypiella and the like,

Arcids such as Hyphantria cunea and the like, Tineids such as linea translucens, Tineola bisselliella and the like;

Diptera:

Culicides such as Culex pipiens pallens, Culex trìtaenìorhynchus, Culex quinquefasciatus and similar, Aedes spp. such as Aedes aeqypti, Aedes albopictus and the like,

Anopheles spp. such as Anopheles sinensis and the like,

Chironomids,

Muscidae such as Musca domestica, Muscina stabulans and the like,

Calliphorids,

Sarcophagids,

Fannidi,

Antomides such as Delia platura, Delia antiqua and the like,

Tefritidi,

Drosophilids,

Phorids like Meqaselìa spìracularìs and the like, Psychodids like Cloqmia albipunctata and the like, Blackflies,

Tabanids,

Stomoxys spp.,

Agromizides and the like;

Beetles:

Diabrotica virgifera vìrgìfera, Diabrotica undecimpunctata howardi and the like,

Scarabeids such as Anomala cuprea, Anomala rufocuprea and the like,

Rincophoridae, Curculionidae and Bruchidae such as Sitophilus zeamais, Lissorhoptrus oryzophilus, Callosobruchus chienensis and the like,

Tenebrionids such as Tenebrio molitor, Tribolium castaneum and the like,

Chrysomelids such as Oulema oryzae, Aulacophora femoralis, Phy Hot reta striolata, Leptinotarsa decemlineata and the like,

Dermestids such as Dermestes maculates and the like, Anobids,

Epilachna spp. such as Epilachna vigintioctopunctata and the like,

Littids,

Bark beetles,

Ptinides,

Cerambicides,

Paederus fuscipes and the like;

Cockroaches: Blattella germanica, Periplaneta fuli -ginosa, Periplaneta americana, Periplaneta brunnea, Blatta orientalis and the like;

Tisanoptera: Thrips palmi, Thrips tabaci, Frankliniella occidentalis, Frankliniella intonsa and the like;

Hymenoptera:

Formicides such as Monomorìum pharaosis, Formica fusca japonìca, Ochetellus glaber, Pristomyrmex pungens, Pheidole noda and the like;

Vespids,

Betylides,

Tentredinids such as Athalia japonìca and the like; Orthoptera:

Grillotalpids, Acridids and the like;

Afanitteri: Ctenocephalìdes felis, Ctenocephalìdes canis, Pulex irritans, Xenopsylla cheopìs and the like;

Anopluri: Pedìculus humanus corporis, Phthri -rus pubis, Haematopìnus eurysternus, Dalmalinia ovìs and the like;

Isoptera:

Underground termites such as Retìculìtermes speratus, Coptotermes formosanus, Retìculìtermes flavi -pes, Retìculìtermes hesperus, Retìculìtermes virgi -nìcus, Retìculìtermes tibialis, Heterotermes aureus and the like,

Dry wood termites such as Incisitermes minor and the like;

Wet wood termites such as Zootermopsis nevadensis and the like;

Mites:

Tetranichids such as Tetranychus urticae, Tetranychus kanzawai, Panonychus cìtrì, Panonychus ulmì, Oligonuchus spp. and similar,

Eriophids such as Aculops pelekassi, Aculus schlechtendali and the like,

Tarsonemids such as Polyphagotarsonemus latus and the like,

Tenuipalpids,

Tucherellidae,

Ixodidae such as Haemaphysalìs longìcornìs, Haemaphysalis flava, Dermacentor variabilis, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophi -lus microplus, Amblyomma americanum, Rhipicephalus sanguineus and the like,

Acarids such as Tyrophagus putrescentiae and the like,

Epidermottidia such as Dermatophagoides farinae, Dermatophagoides ptrenyssnus and the like,

Cheiletids such as Cheyletus eruditus, Cheyletus malaccensis, Cheyletus moorei, Ornithoonyssus bacoti, Ornithonyssus sylvairum and the like,

Dermanissidi such as Dermanyssuys gallinae and the like,

Thrombiculides such as Leptotrombidium akamushi and the like;

Arani: Chiracanthium japonicum, Latrodectus hasseltìì and the like,

Chilopods: Thereuonema hìlgendorfì, Scolopendra subspinipes and the like;

Diplopods: Oxidus gracilis, Nedyopus tambanus and the like;

Isopods: Armadillidium vulgare and the like;

Gastropods: Limax marginatus, Limax flavus and the like.

Examples

Hereinafter, the present invention will be specifically explained according to Examples such as Production Examples, Formulation Examples and Test Examples, but is not limited thereto.

Examples of production of the present compound will be explained.

Production example 1

After mixing 1.39 g of 5-hydroxy-6- (2-propenyl) -1,3-benzodioxole

and 20 ml of anhydrous dimethylformamide, 1.60 g of potassium carbonate, 1.14 g of 2-chloroethylmethylether and 0.7 g of potassium iodide were added to the mixture by cooling with ice, and then stirred at 80 ° C for 8 hours.

The reaction mixture was poured into 30 ml of frozen 5% hydrochloric acid, extracted three times with 40 ml of ethyl acetate while being washed with ethyl acetate. The organic layers were combined and washed with 50 ml of saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and then filtered; and the filtrate was concentrated under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column to obtain 1.10 g of 5- (2-methoxyethoxy) -6- (2-propenyl) -1,3-benzodioxole (hereinafter referred to as the present compound (1) ).

Present compound (1)

1 H-NMR (CDCI3, TMS internal standard) δ (ppm):

3. 30 (m, 2H), 3. 46 (s, 3H), 3.71 (m, 2H), 4 .02 (m, 2H), 5. 00 (m, 2H), 5. 90 (s, 2H) ), 5. 90-5. 97 (m, 1H), 6. 61 (a, 1H), 6. 64 (s, 1H)

Production example 2

After mixing 0.58 g of the present compound (1) and 100 ml of ethyl acetate, 40 mg of platinum oxide were added to the mixture and it was stirred under a hydrogen atmosphere. After confirming the absorption of the amount of hydrogen gas theoretically necessary for the reduction of the 2-propenyl group of the present compound (1), the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The obtained residue was subjected to chromatography on silica gel to obtain 0.56 g of 5- (2-methoxyethoxy) -6-propyl-1,3-benzodioxole (hereinafter referred to as the present compound (2)).

Present compound (2)

1 H-NMR (CDC13, TMS internal standard) δ (ppm):

0. 92 (t, 3H), 1.50-1.56 (m, 2H), 2.50 (m, 2H), 3. 45 (s, 3H), 3.71 (m, 2H), 4. 00 (m, 2H), 5. 90 (s, 2H), 6.51 (s, 1H), 6. 63 (s, 1H)

Production example 3

Except for the use of 2-chloroethylethyl ether instead of 2-chloroethylmethylether, with the same way applied in Production Example 1, 186 mg of 5- (2-ethoxyethoxy) -6- (2-propenyl) - were obtained 1,3-benzodioxole (hereinafter referred to as the present compound (3)).

Present compound (3)

1 H-NMR (CDC1s, TMS internal standard) δ (ppm):

1.20 (t, 3H), 3.30 (m, 2H), 3.56 (q, 2H), 3.75 (m, 2H), 4.02 (m, 2H), 5.00 (m, 2H), 5.8B (s, 2H), 5.90-5.97 (m, 1H), 6.53 (s, 1H), 6.64 (s, 1H)

Production example 4

Except for the use of the present compound (3) instead of the present compound (1), with the same way applied in Production Example 2, 160 mg of 5- (2-ethoxyethoxy) -6-propyl- were obtained 1,3-benzodioxole (hereinafter referred to as the present compound (4)).

Present compound (4)

H-NMR (CDC13, TMS internal standard) δ (ppm):

0.92 (t, 3H), 1.24 (t, 3H), 1.56 (m, 2H), 2.51 (m, 2H), 3.61 (m, 2H), 3-75 (m, 2H), 4.03 (m, 2H) , 5.88 (s, 2H), 6.52 (s, 1H), 6.63 (s, 1H)

Production example 5

After mixing 5.09 g of 5-hydroxy-6- (2-propenyl) -1,3-benzodioxole and 40 ml of anhydrous dimethylformamide, 4.73 g of potassium carbonate was added to the mixture, 5 , 36 g of 2-bromoethanol by cooling with ice, and then stirring at 50 ° C for 48 hours.

The reaction mixture was poured into 30 ml of ice-cold 5% hydrochloric acid solution, extracted three times with 40 ml of ethyl acetate while being washed with ethyl acetate. The organic layers are combined and washed with 50 ml of saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulphate and then filtered; and the filtrate obtained was concentrated under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column to obtain 0.53 g of 5- (2-hydroxyethoxy) -2- (2-propenyl) -1,3-benzodioxole.

5- (2-hydroxyethoxy) -2- (2-propenyl) -1, 3-benzodioxole

1 H-NMR (CDC1a, TMS internal standard) δ (ppm):

2 . 04 (t, 1H), 3. 30 (d, 2H), 3. 92 (m, 2H), 4. 01 (m, 2H), 5. 00 (m, 2H), 5. 90 (s, 2H>, 5.90 (m, 1H), 6.52 (s, 1H), 6.65 (s, 1H)

After mixing 0.14 g of sodium hydride (55% dispersion in mineral oil) and 10 ml of anhydrous dimethylformamide, 0.53 g of 5- (2-hydroxyethoxy) were added to the mixture under ice cooling. -2- (2-propenyl) -1,3-benzodioxole dissolved in 5 ml of anhydrous dimethylformamide, 0.53 g of propyl iodide was added and then stirred at 25 ° C for 12 hours.

The reaction mixture was poured into 20 ml of ice-cold 5% hydrochloric acid solution, extracted three times with 20 ml of ethyl acetate while being washed with ethyl acetate. The organic layers were combined and washed with 20 ml of saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and then filtered; and the filtrate was concentrated under reduced pressure. The residue obtained was subjected to chromatography on a silica gel column to obtain 0.32 g of 5- {2- (propyloxy) ethoxy} -6- (2-propenyl) -1, 3-benzodioxole (hereinafter referred to as the present compound (5)).

Present compound (5)

1 H-NMR (CDC13, TMS internal standard) δ (ppm):

0.95 (t, 3H), 1.60 (m, 2H), 3.30 (d, 2H), 3.50 (m, 2H), 3.75 (m, 2H), 4.05 (m, 2H), 5.00 (m.2H) .5 .B9 (s, 2H), 5.90 (m, 1H), 6.63 (s, 1H), 6.64 (s, 1H) Production example 6

Except for the use of the present compound (5) instead of the present compound (1), in the same way used in Production Example 2, 192 mg of 5 - {(2-propyloxy) ethoxy} -6- were obtained propyl-1,3-benzodioxole (hereinafter referred to as the present compound (6)).

Present compound (6)

1 H-NMR (CDC13, TMS internal standard) δ (ppm):

0.94 (m, 6H), 1.6 (m, 4H), 2.5l (m, 2H), 3.50 (t, 2H), 3.75 (m, 2H), 4.02 (m, 2H), 5.88 (s, 2H), 6.52 (s, 1H), 6.63 (S, 1H)

The present compound will be specifically represented as follows, but the present invention is not constructed limited thereto.

Compound 1,3-benzodioxole represented by Formula (I):

where R <1> and R <2> represent the respective combinations listed in Table 1.

Table 1

Table 1 (continued)

Examples of formulation will then be described. The term "part" represents a part by weight. Also, the present compound will be indicated by the aforementioned compound numbers.

Formulation example 1

Ten parts of any of the present compounds (1) to (9) and 2 parts of permethrin are dissolved in 36 parts of xylene and 36 parts of N, N-dimethylformamide. To this are added 10 parts of polyoxyethylene thyrylphenyl ether and 6 parts of calcium dodecylbenzenesulphonate, and it is mixed by stirring carefully to obtain an emulsion. Formulation example 2

Ten parts of any of the present compounds (1) to (9) and 2 parts of etofenprox are dissolved in 36 parts of xylene and 36 parts of N, N-dimethylformamide. To this are added 10 parts of polyoxyethylene thyrilphenylether and 6 parts of calcium dodecylbenzenesulphonate and it is mixed by careful stirring to obtain an emulsion.

Formulation example 3

Five parts of SORPOL 5060 (registered trademark of TOHO Chemical Industry Co., LTD.) Is added to the mixture consisting of 40 parts of any of the present compounds (1) up to (9) and 8 parts of tetramethrin, and it is mixed thoroughly . Then 28 parts of CARPLEX # 80 (registered trademark of Shionogi & Co., Ltd., synthetic anhydrous silicon oxide fine powder) and 19 parts of 300 mesh diatomaceous earth are added, and mixed with a juice blender for obtain a wettable powder.

Formulation example 4

Ten parts of any of the present compounds (1) to (9), 2 parts of phenothrin, 35 parts of silica powder containing 50 parts of ammonium sulfate salt of polyoxyethylene alkyl ether sulfate and 53 parts of water are mixed and then finely divided by a wet grinding process to obtain a preparation.

Formulation example 5

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of prallethrin are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain an oil solution.

Formulation example 6

0.5 parts of any of the present compounds (1) to (9), 0.1 parts of cyphenothrin and 49.4 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd) are placed in an aerosol container. An aerosol valve is mounted on a container and the container is then loaded with 25 parts of dimethylether and 25 parts of LPG. The container is beaten and an actuator is mounted on the container to obtain an oily aerosol.

Formulation example 7

An aerosol container is loaded with 3 parts of any of the present compounds (1) to (9), 0.6 parts imiprothrin, 0.01 parts BHT, 5 parts xylene, a mixture of 3.39 parts of refined kerosene and 1 part of emulsifying agent [Atmos 300 (trade name of Atmos Chemical Ltd.)] and 47 parts of distilled water. A valve part is connected to the container and the container is then loaded with 40 parts of a propellant (LPG) through the valve under pressure to obtain an aqueous aerosol.

Formulation example 8

Three grams of any of the present compounds (1) to (9) and 0.5g of transfluthrin are dissolved in 20ml of acetone and then mixed evenly together with 96.2g of a mosquito coil carrier [a mixture of taboo powder (Machilus thunbergii powder): waste powder (powder of parts other than the active component of pyrethrum): wood powder at a weight ratio of 4: 3: 3] and 0.3 g of green pigment by agitation. To this are added 120 ml of water. The mixture is carefully kneaded, molded and then dried to obtain a mosquito spiral.

Formulation example 9

Three grams of any of the present compounds (1) to (9) and 0.5 g of 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl-1R-trans-2,2-dimethyl-3 - (2-methylprop-1-enyl) cyclopropanecarboxylate are dissolved in 20 ml of acetone and then mixed evenly together with 96.2 g of mosquito coil carrier [a mixture of tabu powder (Machilus thunbergii powder): waste (dust from parts other than the active component of pyrethrum): wood dust at a weight ratio of 4: 3: 3] and 0.3 g of green pigment by shaking. To this are added 120 ml of water. The mixture is carefully kneaded, molded and then dried to obtain a mosquito spiral.

Formulation example 10

Three grams of any of the present compounds (1) to (9) and 0.5 g of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R-trans-3- (1-propenyl (E / Z ) = 1/8)) - 2,2-dimethylcyclopropanecarboxylate are dissolved in 20 ml of acetone and then mixed evenly together with 96.2 g of a mosquito coil carrier [a mixture of tabu powder (Machilus thunbergii powder) : waste powder (powder of parts other than the active component of pyrethrum): wood powder at a weight ratio of 4: 3: 3] and 0.3 g of green pigment by shaking. Add to this 120 ml of water. The mixture is carefully kneaded, molded and then dried to obtain a mosquito spiral.

Example of wording il

One part of any of the present compounds (1) up to (9), 0.2 parts of d-allethrin, 0.2 parts of phenothrin and 48.6 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.) are placed in an aerosol container and an aerosol valve is mounted on the container. The container is then loaded with 25 parts of dimethyl ether and 25 parts of LPG and beaten. An actuator for a full quantity spray type aerosol is mounted on the container to obtain an aerosol.

Formulation example 12

One part of any of the present compounds (1) to (9), 0.2 parts of tetramethrin, 0.2 parts of permethrin and 48.6 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.), are placed in an aerosol container and an aerosol valve is mounted on the container. The container is then loaded with 25 parts of dimethyl ether and 25 parts of LPG and beaten. An actuator for a full quantity spray type aerosol is mounted on the container to obtain an aerosol.

Formulation example 13

One part of any of the present compounds (1) to (9), 0.2 parts of prallethrin, 0.2 parts of cyphenothrin and 48.6 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.), are placed in an aerosol container and an aerosol valve is mounted on the container. The container is then loaded with 25 parts of dimethyl ether and 25 parts of LPG and beaten. An actuator for a full quantity spray type aerosol is mounted on the container to obtain an aerosol.

Formulation example 14

One part of any of the present compounds (1) to (9), 0.2 parts of imiprothrin, 0.2 parts of resmethrin and 48.6 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.), are placed in an aerosol container and an aerosol valve is mounted to the container. The container is then loaded with 25 parts of dimethyl ether and 25 parts of LPG and beaten. An actuator for a full quantity spray type aerosol is mounted on the container to obtain an aerosol.

Formulation example 15

One part of any of the present compounds (1) to (9), 0.2 parts of 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl-1R-trans-3- (1-propenyl (E / Z = 1/8)) - 2,2-dimethylcyclopropanecarboxylate, 0.2 parts of permethrin and 48.6 parts of NEO-THIOZOL (Chuo Kasei Co., Ltd.), are placed in an aerosol container and an aerosol valve it is mounted on the container. The container is then loaded with 25 parts of dimethyl ether and 25 parts of LPG and beaten. An actuator for a full quantity spray type aerosol is mounted on the container to obtain an aerosol.

Formulation example 16

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of deltamethrin are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 17

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of cyhalothrin are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 18

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of fenvalerate are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 19

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of bifenthrin are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 20

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of empenthrin are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 21

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of fenitrothion are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 22

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of metoxadiazone are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil. Formulation example 23

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of hexaflumuron are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 24

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of diflubenzuron are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil. Formulation example 25

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of bistrifluron are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 26

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of pyriproxyphen are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 27

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of imidacloprid are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 28

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of ethoxazole are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

Formulation example 29

0.5 parts of any of the present compounds (1) to (9) and 0.1 parts of amidoflumet are dissolved in 10 parts of dichloromethane. This solution is mixed with 89.4 parts of Isopar M (isoparaffin: registered trademark of Exxon Chemical) to obtain a solution in oil.

The following Test Example demonstrates the efficacy of the pesticide composition containing the present compound and an active ingredient as a pesticide, to control harmful insects. The present compounds are represented by the compound numbers defined above.

Test example

After mixing the present compounds (1), (2), (3), (4), (5) and (6) respectively with dallethrin, acetone solutions are prepared containing each mixture with the respective prescribed concentrations (weight / volume) listed in Table 2. 0.5 μl of the acetone solution is applied to an adult female housefly by dripping it onto the back of its chest region, transferred to a plastic cup having a diameter of about 9 cm and a height of about 4 , 5 cm, and then left at 25 ° C with feeding represented by a 5% aqueous solution of sugar. After 24 hours, live and dead house flies are observed to obtain a mortality rate. The number of house flies contained in each cup was 10, and the test was repeated twice.

Furthermore, after preparation of acetone solutions containing each of the present compounds (1), (2), (3), (4), (5) and (6) and d-allethrin at the respective prescribed concentrations (w / v) listed in Table 2, a test was performed in the same manner mentioned above.

For comparison, using 4,5-methylenedioxy-2-propylphenyl-2-butoxyethyl ether (hereinafter referred to as the comparative compound)

instead of the present compounds, a test was performed in the same way. The results are shown in Table 2.

Table 2

Table 2 (continued)

Industrial applicability

The addition of the present compound together with an active ingredient as a pesticide in a pesticide composition enhances the pest control effect of the pesticide composition.

Claims (10)

CLAIMS 1. Compound 1,3-benzodioxole represented by Formula (I): wherein R1 represents a C3 alkyl group or a C3 alkenyl group, and R2 represents a C1-3 alkyl group. Compound 1,3-benzodioxole according to claim 1, wherein R1 is a propyl group or a 2-propenyl group. Compound 1,3-benzodioxole according to claim 1, wherein R2 is a methyl group. Compound 1,3-benzodioxole according to claim 1, wherein R2 is an ethyl group. Compound 1,3-benzodioxole according to claim 1, wherein R2 is a propyl group. 6. Pesticidal composition comprising a 1,3-benzodioxole compound represented by Formula (I): wherein R1 represents a C3 alkyl group or a C3 alkenyl group, and R2 represents a C1-3 alkyl group and an active ingredient as a pesticide. 7. A pesticidal composition according to claim 6, wherein the active ingredient as a pesticide is a pyrethroid compound. 8. A process for controlling a pest by applying an effective amount of a 1,3-benzodioxole compound represented by Formula (I) wherein R <1> represents a C3 alkyl group or a C3alkenyl group, and R <2> represents a C1-3 alkyl group; and an active ingredient as a pesticide to a harmful insect or its biotope. A method for controlling a pest according to claim 8, wherein the active ingredient as a pesticide is a pyrethroid compound. Use of the 1,3-benzodioxole compound according to claim 1 to control a pest by application to a pest or a biotope thereof together with an active ingredient as a pesticide.