JP2002012507A - Insecticidal and acaricidal compositions - Google Patents

Abstract

(57) [Problem] To provide an insecticide / miticidal agent having an excellent insecticidal / miticidal effect. A specific dihalopropene compound (for example, 3,5-dichloro-4- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) -1-)
(3,3-dichloro-2-propenyloxy) benzene) The surface tension of a 1% by weight aqueous solution is 40 dyne / cm.
By using the above-mentioned dispersant and a composition containing an organic compound which is liquid at room temperature and water having a solubility in 100 g of water at 20 ° C. of 1 g or less, excellent insecticidal and acaricidal efficacy can be obtained.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a novel insecticidal and acaricidal composition.

[0002]

BACKGROUND OF THE INVENTION At present, a large number of insecticides and acaricides are commercially available and used. However, there are many types of pests and mites to be controlled, and in the field of agriculture, those that can be used in smaller amounts are required from the viewpoint of environmental problems and economics. There is a need for insecticides and acaricides that are effective. In addition, in order to obtain a sufficient insecticidal / miticidal effect, the formulated insecticide / miticidal active ingredient-containing composition is required to have the stability of the preparation (for example, the stability of the pesticidal / miticidal active ingredient in the preparation, the uniformity). Sex) is required.

[0003]

As a result of intensive studies, the present inventor has found that a specific dihalopropene compound, a dispersant having a surface tension of a 1% by weight aqueous solution of 40 dyne / cm or more, and 100 g of water at 20 ° C. 1g solubility
The present inventors have found that excellent insecticidal and acaricidal efficacy can be obtained by using the following composition containing a liquid organic compound and water at normal temperature, and have accomplished the present invention.

That is, the present invention relates to

Embedded image Wherein Z represents an oxygen atom, a sulfur atom or an NR ⁴ group (where R ⁴ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms), and Y represents an oxygen atom, a sulfur atom or N 2
X represents a chlorine atom or a bromine atom independently, and R ² , R ³ and R ¹⁰ each independently represent a halogen atom, a haloalkyl group having 1 to 3 carbon atoms or a group having 1 to 3 carbon atoms. represents 3 alkyl group, t represents an integer of 0 to 2, R ¹ has the formula

Embedded image In the formula, A represents an optionally substituted heterocyclic group. B is
Oxygen atom, S (O) q group, NR ⁹ group, C (= G ¹⁾ represents a G ² group or G ¹ C (= G ²⁾ group, q represents an integer of 0 to 2, R ⁹ is hydrogen An atom, an acetyl group or an alkyl group having 1 to 3 carbon atoms, G ¹ and G ² each independently represent an oxygen atom or a sulfur atom, and R ⁵ , R ⁶ , R ⁷ ,
R ¹¹ and R ¹² each independently represent a hydrogen atom,
To ¹³ represent an alkyl group or a trifluoromethyl group; R ¹³ and R ¹⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a trifluoromethyl group or a halogen atom; Represents an integer from to 6,
s represents an integer of 1 to 6. Q ₁ , Q ₂ , Q indicated by｝
₃ represents a Q _4, Q _5, Q ₆ or Q _7. (Hereinafter referred to as the present compound), a dispersant having a 1% by weight aqueous solution having a surface tension of 40 dyne / cm or more (hereinafter referred to as the present dispersant), and water 1 at 20 ° C.
An insecticidal / miticidal composition containing an organic compound that is liquid at room temperature and has a solubility of 1 g or less in 00 g (hereinafter, referred to as the present solvent) and water (hereinafter, referred to as the present composition).
It is about.

[0005]

BEST MODE FOR CARRYING OUT THE INVENTION In the present compound, examples of the heterocyclic group of the “optionally substituted heterocyclic group” as the definition of the substituent A include isoxazole, isothiazole, thiazole, 1,3,3 4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 1,
2,3-triazole, 1,2,4-triazole,
1,2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2,4-triazine,
1,3,5-triazine, indole, benzofuran,
Thianaphthalene, indazole, benzimidazole,
Benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, piperidine, piperazine, tetrahydrofuran, tetrahydropyran, pyrazoline, phthalimide, dioxane, dioxolan, benzodioxolan, etc. Examples of the substituent that can be performed include (R ⁸ ) _r, wherein R ⁸ is a halogen atom, a nitro group, a cyano group, an alkyl group having 1 to 4 carbon atoms,
Haloalkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 4 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, 1 to 1 carbon atoms
3 alkylthio groups, haloalkylthio groups having 1 to 3 carbon atoms, alkylsulfinyl groups having 1 to 2 carbon atoms, 1 carbon atoms
Alkylsulfonyl group having 1 to 2 carbon atoms, haloalkylsulfinyl group having 1 to 2 carbon atoms, haloalkylsulfonyl group having 1 to 2 carbon atoms, alkenyl group having 2 to 4 carbon atoms, 2 to 4 carbon atoms
Haloalkenyl group, a C2-4 alkynyl group, a C2-4 haloalkynyl group, an amino group, a dimethylamino group, an acetamido group, an acetyl group, a haloacetyl group, a formyl group, a carboxyl group, a methoxycarbonyl group, A cycloalkyl group having 3 to 6 carbon atoms, (1 to 2 carbon atoms)
Alkyl) aminocarbonyl group, [di (C 1-2
Or a phenyl group, a benzyl group, a phenoxy group, a benzyloxy group, a pyridyloxy group (the phenyl and pyridyl rings of these substituents are a halogen atom, an alkyl group having 1 to 4 carbon atoms,
It may be substituted by a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a haloalkoxy group having 1 to 4 carbon atoms. ) And r represent an integer of 0 to 7. ｝.

[0006] Among the present compounds,

Embedded image 3,5-dichloro-4- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) represented by
-1- (3,3-Dichloro-2-propenyloxy) benzene is preferred as the active ingredient of the composition of the present invention.

The present compound can be produced according to the method described in JP-A-9-151172.

[0008] In the composition of the present invention, the compound of the present invention is usually contained in an amount of 0.
The content is 1 to 40% by weight, preferably 1 to 30% by weight, more preferably 2 to 20% by weight.

The dispersant includes, for example, natural products having a sugar structure or an alkyl structure in a main chain structure having a solubility in water at 20 ° C. of 1% by weight or more and derivatives thereof; And a protein having a solubility in water at 20 ° C. of 1% by weight or more. Examples of natural products having a sugar structure or an alkyl structure in the main chain structure having a solubility in water at 20 ° C. of 1% by weight or more and derivatives thereof include gum arabic, pectin, xanthan gum, locust gum, alginic acid and salts thereof, Carboxymethylcellulose and its salts and ligninsulfonate.
Examples of the synthetic polymer having a solubility in water at 20 ° C. of 1% by weight or more include polyvinyl alcohol, polyvinyl methyl ether, polyethylene glycol, polyvinyl pyrrolidone, hydroxypropyl cellulose,
Hydroxypropyl methylcellulose and sodium polyacrylate. Examples of the protein having a solubility in water at 20 ° C. of 1% by weight or more include gelatin, casein, and protamine. The molecular weight of the present dispersant is not particularly limited as long as the composition of the present invention can be obtained.
1,000,000, preferably an average molecular weight of 1
It is in the range of 000 to 200,000. The viscosity of the dispersant is usually 1 at 20 ° C. from the viewpoint of handleability.
The viscosity of the aqueous solution by weight is 10,000 mPa · s or less, preferably 5,000 mPa · s or less. The dispersant is generally contained in the composition of the present invention in an amount of 0.1 to 20% by weight, preferably 0.5 to 10% by weight, and more preferably 1 to 10% by weight.
-5% by weight.

As the present solvent, for example, an aromatic solvent,
Animal and vegetable oils, paraffinic solvents and ester solvents can be mentioned.

Examples of the aromatic solvent include xylene, alkylbenzene and alkylnaphthalene. Animal and vegetable oils include, for example, rapeseed oil, soybean oil, and linseed oil. Examples of the paraffin-based solvent include normal paraffins having 5 or more carbon atoms, isoparaffins having 5 or more carbon atoms, and cycloparaffins having 5 or more carbon atoms,
Normal paraffin having preferably about 5 to 70 carbon atoms,
Examples thereof include isoparaffins having about 5 to 200 carbon atoms and cycloparaffins having about 5 to 200 carbon atoms, and more preferably normal paraffins having about 5 to 45 carbon atoms, isoparaffins having about 5 to 100 carbon atoms, and carbon numbers. About 5 to 100 cycloparaffins can be mentioned. Examples of the ester solvent include diisobutyl adipate, diisodecyl adipate, dialkyl phthalate (such as didecyl phthalate), octyl oleate, lauryl oleate, octyl dodecyl oleate, and isopropyl myristate.

The present solvent can be used alone or as a mixture of two or more. From the viewpoint of the insecticidal and acaricidal efficacy of the composition of the present invention, a mixed solvent of a paraffin solvent and an ester solvent or an aromatic solvent is preferred. It is preferable to use The present solvent contains a mixed solvent of a paraffin solvent and an ester solvent, and further contains 3,5-
Dichloro-4- (3- (5-trifluoromethyl-2-
When the composition of the present invention containing (pyridyloxy) propyloxy) -1- (3,3-dichloro-2-propenyloxy) benzene is in the form of an emulsion (described later), the paraffinic solvent may be a cycloparaffinic solvent. More preferred.

The amount of the solvent contained in the composition of the present invention can be determined in an appropriate amount depending on the ease of production of the composition of the present invention, the purpose of use of the composition of the present invention, etc. In general, the content can be 0.5 to 50 times by weight, preferably 1 to 30 times by weight, more preferably 1.5 to 10 times by weight.

Specific examples of the solvent include, for example, Hisol SAS-296 (a mixture of 1-phenyl-1-xylylethane and 1-phenyl-1-ethylphenylethane, trade name of Nippon Oil Co., Ltd.), and Hisol SAS-296.
LH (trade name of Nippon Oil Co., Ltd.), Shersol A
(Trade name of Shell Chemical Co., Ltd.), Shell Sol AB
(Shell Chemical Co., Ltd.), Shell Sol E (Shell Chemical Co., Ltd.), Shell Sol R (Shell Chemical Co., Ltd.), Shell Sol T (Shell Chemical Co., Ltd.), Shell Zol D-70 (trade name of Shell Chemical Co., Ltd.),

Cactus Solvent HP-MN (methylnaphthalene 80%, trade name of Nikko Petrochemical Co., Ltd.), Cactus Solvent HP-DMN (dimethylnaphthalene)
80%, trade name of Nikko Petrochemical Co., Ltd.), Cactus Solvent P-100 (alkylbenzene having 9 to 10 carbon atoms, trade name of Nikko Petrochemical Co., Ltd.), Cactus Solvent P-150 (alkylbenzene, Nikko Petrochemical Co., Ltd.) Cactus Solvent P-180 (mixture of methyl naphthalene and dimethyl naphthalene, trade name of Nikko Petrochemical Co., Ltd.), Cactus Solvent P-20
0 (a mixture of methylnaphthalene and dimethylnaphthalene,
Cactus Solvent P-220 (mixture of methyl naphthalene and dimethyl naphthalene, trade name of Nikko Petrochemical Co., Ltd.), Cactus Solvent PAD-1 (dimethyl monoisopropyl naphthalene, Nikko Petrochemical Co., Ltd.) Brand name), Solvesso 1
00 (aromatic hydrocarbon, trade name of ExxonMobil Chemical Co., Ltd.), Solvesso 150 (aromatic hydrocarbon, trade name of ExxonMobil Chemical Co., Ltd.), Solvesso 20
0 (aromatic hydrocarbon, trade name of ExxonMobil Chemical Co., Ltd.),

Swazol 100 (toluene, trade name of Maruzen Oil Co., Ltd.), Swazol 200 (xylene, trade name of Maruzen Petroleum Co., Ltd.),

Vinicizer 20 (diisotridecyl phthalate, trade name of Kao Corporation), Vinicizer 40
(Diisobutyl adipate, trade name of Kao Corporation),
Vinicizer 50 (diisodecyl adipate, trade name of Kao Corporation), Vinicizer 85 (dialkyl phthalate, trade name of Kao Corporation), Vinicizer 105 (didecyl phthalate, trade name of Kao Corporation) Vinicizer 124 (trade name of Kao Corporation) , Kao Corporation), Exepearl O-OL (Octyl Oleate, Kao Corporation), Exepearl L-OL (Lauryl Oleate, Kao Corporation), Exepearl OD-OL (Oleic Acid) Octyldodecyl, product name of Kao Corporation),

Toxanone PP-1000 (polyoxypropylene glycol, trade name of Sanyo Chemical Industries, Ltd.)

Nikkor IPA-A (isopropyl myristate, trade name of Nikko Chemical Co., Ltd.), Nikkor IPA-EX (isopropyl myristate, trade name of Nikko Chemical Co., Ltd.),

TECLEAN N-30 (trade name of Nippon Oil Co., Ltd.), TECLEAN N-32 (trade name of Nippon Oil Co., Ltd.), TECLEAN N-33 (trade name of Nippon Oil Co., Ltd.),

Machine oil 46P (trade name of Japan-US Mineral Oil Co., Ltd.), pesticide machine oil P (trade name of Japan-US Mineral Co., Ltd.),
Pesticide oil H (trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil A (trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil B (trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil C
(Trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil D (trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil E (trade name of Japan-US Mineral Oil Co., Ltd.), Super Oil F (Japan-US Mineral Oil Co., Ltd.) No. 1 spindle oil (trade name of Japan-US Mineral Oil Co., Ltd.), No. 2 spindle oil (trade name of Japan-US Mineral Oil Co., Ltd.), B machine oil (trade name of Japan-US Mineral Oil Co., Ltd.) Product name),
C machine oil (trade name of US-Japan Mineral Oil Co., Ltd.),

Naphthesol M (paraffinic solvent, trade name of Nippon Petrochemical Industry Co., Ltd.), Isosol 300
(Trade name of Nippon Petrochemical Industry Co., Ltd.), Isosol 400 (trade name of Nippon Petrochemical Industry Co., Ltd.),

Exol D80 (mixed solvent of paraffin and cycloparaffin, trade name of ExxonMobil Chemical Co., Ltd.), Exol D110 (mixed solvent of paraffin and cycloparaffin, trade name of ExxonMobil Chemical Co., Ltd.), Exol D130 (paraffin and paraffin) Cycloparaffin mixed solvent, ExxonMobil Chemical Co., Ltd.), Exol D160 (paraffin and cycloparaffin mixed solvent, ExxonMobil Chemical Co., Ltd.), Isopar E (Kerosine, ExxonMobil Chemical Co., Ltd.) ), Isopar G (Kerosine, trade name of ExxonMobil Chemical Co., Ltd.), Isopar H
(Kerosine, trade name of ExxonMobil Chemical Co., Ltd.), Isopar M (Kerosine, trade name of ExxonMobil Chemical Co., Ltd.),

Neothiozole (Kerosine, trade name of Chuo Kasei Co., Ltd.),

IP Solvent 2028 (isoparaffinic oil, trade name of Idemitsu Petrochemical Co., Ltd.), IP Solvent 2835 (isoparaffinic oil, trade name of Idemitsu Petrochemical Co., Ltd.),

Naplex 38 (naphthenic oil, trade name of ExxonMobil Oil Co., Ltd.), White Rex 205 (trade name of ExxonMobil Oil Co., Ltd.), White Rex 207 (trade name of ExxonMobil Petroleum Co., Ltd.), white Rex 215 (trade name of ExxonMobil Oil Co., Ltd.), White Rex 247 (trade name of Exxon Mobil Petroleum Co., Ltd.), White Rex 2210 (trade name of Exxon Mobil Petroleum Co., Ltd.), White Rex 307 (Exxon Mobil Petroleum Co., Ltd.) Brand name), White Rex 30
9 (trade name of ExxonMobil Sekiyu KK), White Rex 326 (trade name of Exxon Mobil Sekiyu KK) and White Rex 335 (trade name of Exxon Mobil Sekiyu KK).

The composition of the present invention is a preparation in which fine particles substantially insoluble in the aqueous phase are dispersed together with the present dispersant in the aqueous phase. The composition of the present invention can take various pharmaceutical forms such as a capsule suspension, a capsule suspoemulsion, a suspoemulsion, and an emulsion.

As the form of the capsule suspension,
The oil droplets obtained by dissolving the present compound in the present solvent are encapsulated, and the capsules are suspended in an aqueous phase, and the oil droplets obtained by dispersing the present compound in the present solvent are encapsulated.
A form in which the capsule is suspended in an aqueous phase may be mentioned. Examples of the form of a capsule suspoemulsion include a form in which a solid or liquid compound of the present invention is encapsulated, the capsules are suspended in an aqueous phase, and the solvent is emulsified in an aqueous phase. As a form of the suspoemulsion, a form in which the solid compound is suspended in the aqueous phase and the solvent is emulsified in the aqueous phase, and oil droplets in which the solid compound is suspended in the solvent are The aqueous phase may be in the form of an emulsion.
Examples of the form of the emulsion include a form in which oil droplets containing the present compound and the present solvent are emulsified in an aqueous phase.

In the composition of the present invention in the form of a capsule suspension or a capsule suspension emulsion, the composition is usually 0.1 to 50 μm, preferably 0.3 to 40 μm, more preferably 0.5 to 30 μm, and more preferably 2 to 25 μm.
Capsules (microcapsules) adjusted to a volume median diameter of about μm are dispersed in the aqueous phase containing the present dispersant.
Examples of the membrane material forming the capsule include polyurea, polyurethane, polyamide, urea formalin resin,
Melamine formalin resin, gelatin, albumin, chitosan and the like.

The volume average particle diameter of the present solvent in the capsule suspoemulsion is usually 0.1 to 50 μm, preferably 0.3 to 40 μm, more preferably 0.5 to 3 μm.
0 μm, more preferably about 2 to 25 μm.

The composition of the present invention, which is in the form of a suspoemulsion, comprises a composition in which microdroplets (emulsion particles) of the present solvent are emulsified in an aqueous phase and the present compound is dispersed in emulsion particles or an aqueous phase. Things. The present compound and the volume average particle diameter of the present compound in the suspoemulsion are usually 0.1 to 50 μm, preferably 0.3 to 40 μm.
m, more preferably about 0.5 to 30 μm, more preferably about 2 to 25 μm.

The composition of the present invention in the form of an emulsion is a composition in which the present compound is dissolved in the present solvent, or a composition in which fine droplets of a mixed solution of the present compound and the present solvent are emulsified in an aqueous phase. is there. The particle diameter of the micro liquid droplet is usually 0.1 to
50 μm, preferably 0.3 to 40 μm, more preferably 0.5 to 30 μm, more preferably 2 to 25 μm
It is about.

The composition of the present invention may further comprise, if necessary, a viscosity modifier, a surfactant, an antifoaming agent, an antifreezing agent, a preservative,
It may contain stabilizers, colorants, fragrances, potency enhancers, safeners and the like.

Examples of the viscosity modifier include natural polysaccharides such as xanthan gum, ramzan gum, locust bean gum, carrageenan, and werant gum; synthetic polymers such as sodium polyacrylate; semi-synthetic polymers such as carboxymethyl cellulose; aluminum silicate; , Bentonite, heclite, fumed silica, etc., and alumina sol. As Xanthan gum, for example, Kelzan S (manufactured by Monsanto)
Examples of the aluminum silicate include Vegum R (manufactured by Vanderbilt). Examples of the dry silica include Aerosil 200 (manufactured by Degussa Hurth), and examples of the mixture of dry silica and alumina sol include Aerosil COK-84 (manufactured by Degussa Hurth).

When a viscosity modifier is used, its amount is usually 0.01 to 10% by weight, preferably 0.1 to 5% by weight in the present composition.

As the surfactant, a nonionic surfactant, an anionic surfactant, a cationic surfactant, and an amphoteric surfactant are used. Nonionic surfactants include, for example, sugar ester type nonionic surfactants, fatty acid ester type nonionic surfactants, vegetable oil type nonionic surfactants, alcohol type nonionic surfactants, and alkylphenol type nonionic surfactants , Polyoxyethylene / polyoxypropylene block polymer type nonionic surfactant, bisphenol type nonionic surfactant, polyaromatic ring type nonionic surfactant, silicon type nonionic surfactant and fluorine type nonionic surfactant Can be mentioned.

Examples of the sugar ester type nonionic surfactant include sorbitan fatty acid ester, polyoxyethylene sorbitan aliphatic ester and sucrose fatty acid ester. Examples of the fatty acid ester type nonionic surfactant include polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, and polyoxyethylene fatty acid diesters. Examples of the vegetable oil type nonionic surfactant include polyoxyethylene castor oil and polyoxyethylene hydrogenated castor oil. Examples of the alcohol type nonionic surfactant include polyoxyethylene alkyl ether. Examples of the alkylphenol-type nonionic surfactant include polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, and polyoxyethylene alkylphenyl ether / formalin condensate. Examples of the polyoxyethylene / polyoxypropylene block polymer type nonionic surfactant include polyoxyethylene / polyoxypropylene block polymer, alkyl polyoxyethylene / polyoxypropylene block polymer ether, and alkylphenyl polyoxyethylene / polyoxypropylene. And block polymer ethers. Examples of the bisphenol-type nonionic surfactant include polyoxybisphenyl ether. Examples of the polyaromatic ring type nonionic surfactant include polyoxyalkylene benzyl phenyl ether and polyoxyalkylene styryl phenyl ether. Examples of the silicon type nonionic surfactant include a polyoxyethylene ether type silicone type surfactant and a polyoxyethylene ester type silicon type surfactant.

Examples of the anionic surfactant include a sulfate-type anionic surfactant, a sulfonate-type anionic surfactant, a phosphate-type anionic surfactant, and a carboxylic acid-type anionic surfactant. Can be mentioned. Examples of the sulfate type anionic surfactant include alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxystyryl phenyl ether sulfate, and polyoxyethylene / polyoxypropylene block polymer sulfate. Examples of the sulfonate-type anionic surfactant include paraffin sulfonate, dialkyl sulfosuccinate, alkylbenzene sulfonate, monoalkyl naphthalene sulfonate, dialkyl naphthalene sulfonate, naphthalene sulfonate / formalin condensate, and alkyl Diphenyl ether disulfonate and polyoxyethylene alkyl phenyl ether sulfonate. Examples of the phosphate type anionic surfactant include polyoxyethylene alkyl ether phosphate, polyoxyethylene monoalkyl phenyl ether phosphate, polyoxyethylene dialkyl phenyl ether phosphate,
Examples include polyoxyethylene styryl phenyl ether phosphate, polyoxyethylene / polyoxypropylene block polymer phosphate, and alkyl phosphate. Examples of the carboxylic acid type anionic surfactant include fatty acid sodium, fatty acid potassium, fatty acid ammonium, N-methyl-sarcosinate, sodium resinate and potassium resinate.

Examples of the cationic surfactant include an ammonium type cationic surfactant and a benzalkonium type cationic surfactant. Examples of the ammonium-type cationic surfactant include alkyltrimethylammonium chloride, methylpolyoxyethylenealkylammonium chloride, alkyl N-methylpyridinium bromide, mono- or dialkylmethylated ammonium chloride, and alkylpentamethylpropylenediamine chloride. Examples of the benzalkonium-type cationic surfactant include alkyldimethyl benzalkonium chloride, benzethonium chloride and octylphenoxyethoxyethyldimethylbenzylammonium chloride.

Examples of the amphoteric surfactant include a betaine-type amphoteric surfactant. Examples of betaine-type amphoteric surfactants include dialkyldiaminoethylbetaine and alkyldimethylbenzylbetaine. When a surfactant is used, its amount is usually 0.1 to 20% by weight, preferably 1 to 10% by weight in the present composition.
% By weight.

Examples of the antifoaming agent include antifoam C
(Trade name of Dow Corning), Antifoam CE
(Trade name of Dow Corning), TSA730 (trade name of Toshiba Silicone), TSA731 (trade name of Toshiba Silicone), TSA732 (trade name of Toshiba Silicone), YMA6509 (trade name of Toshiba Silicone)
Silicone defoamer and Fluoro wet PL80
(Trade name of Clariant) and the like. When an antifoaming agent is used, its amount is usually 0.001 to 3% by weight in the composition of the present invention.

Examples of the antifreeze include water-soluble glycols such as propylene glycol. When an antifreezing agent is used, its amount is usually 0.5 to 30% by weight, preferably 1 to 20% by weight, more preferably 5 to 10% by weight in the composition of the present invention.

Examples of preservatives include p-hydroxybenzoic acid ester, salicylic acid derivative, isothiazoline-
3-one derivatives (for example, Bio Hope L (trade name of K-I Kasei)) and the like. When a preservative is used, its amount is usually 0.01 to 5% by weight, preferably 0.05 to 3% by weight, more preferably about 0.1 to 1% by weight in the composition of the present invention.

If necessary, the composition of the present invention may contain other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, insect growth regulators, fertilizers, soil conditioners, Strength agent,
It may contain an adjuvant or the like.

Next, a method for producing the composition of the present invention will be described.
When the composition of the present invention is in the form of a capsule suspension or capsule suspension emulsion, microcapsules are produced. Examples of the microencapsulation method include known methods such as an interfacial polymerization method, an in-situ method, a phase separation (coacervation) method, and a submerged drying method.

The microencapsulation method and the type of the membrane substance can be appropriately selected depending on the purpose. The present compound may be microencapsulated as it is, or may be microencapsulated after dissolving or dispersing the present compound in the present solvent in advance. The composition of the present invention in the form of a capsule suspension is first prepared in advance using the water containing the present dispersant to prepare an aqueous dispersion of microcapsules by the microencapsulation method described above, and then prepared in a separate step as necessary. Further, it can be produced by mixing with a thickener liquid containing a viscosity modifier, an antifoaming agent, an antifreezing agent, a preservative and the like. The composition of the present invention in the form of a capsule suspoemulsion is prepared by dissolving the present dispersant in water, and then using the water to microencapsulate the solid or liquid compound in advance by the microencapsulation method described above. To obtain an aqueous dispersion of the microcapsules, in which the present solvent is emulsified, and then, if necessary, a thickener containing a viscosity modifier, an antifoaming agent, an antifreezing agent, a preservative, etc. It can be produced by mixing with a solution.

When the composition of the present invention is in the form of a suspoemulsion, for example, the present dispersant is dissolved in water, then the present compound, the present solvent, and if necessary, a viscosity modifier,
After adding and mixing auxiliaries such as antifoaming agent, antifreezing agent and preservative,
It can be obtained by simultaneously performing pulverization dispersion and emulsification using a wet pulverization method using a medium such as glass beads or zirconia. Whether the present compound is present in the microdroplets of the present solvent or in the aqueous phase is determined by the type of the present compound, the present solvent, and the present dispersant. As the present solvent, those which do not substantially dissolve the solid or semi-solid compound of the present invention are used. Further, a compound capable of dissolving the present compound may be used in a ratio smaller than the solubility of the present compound. The composition of the present invention in the form of a suspoemulsion may be prepared by separately preparing an emulsion in which the solvent is emulsified and a suspension in which the solid compound is suspended, and then mixing them. It is manufactured by pulverizing and dispersing the solid compound in an emulsion in which the prepared solvent is emulsified, or emulsifying the solvent in a suspension prepared by pulverizing and dispersing a solid compound prepared in advance. You can also.

When the composition of the present invention is in the form of an emulsion, it can be produced by the following method. When the present compound is a solid or semi-solid at room temperature, the present compound is dissolved in the present solvent in advance, and the solution is dissolved in water containing the present dispersant (if necessary, a viscosity modifier, an antifoaming agent, an antifreezing agent, a preservative). And the like may be contained.). When the present compound is liquid at room temperature, the present solvent and the present compound are mixed in advance, and the solution is mixed with water containing the present dispersant (if necessary, a viscosity modifier, an antifoaming agent, an antifreezing agent, a preservative, And the like may also be contained.).

The dispersant can be gradually added during the emulsification and dispersion process. In this production method, as a method for emulsifying and dispersing a solution (hereinafter, referred to as the present solution) obtained by dissolving the present compound in the present solvent or mixing with the present solvent, a mechanical dispersion method is used. And a phase inversion method.

In the present application, the mechanical dispersion method is a method of emulsifying and dispersing the present solution in water by applying a high mechanical shearing force to a liquid comprising two layers of the present solution and water.
Specific examples of the mechanical dispersion method include (1)
A method of emulsifying and dispersing a liquid consisting of two layers of water containing the present solution and the present dispersant at a high speed; (2) forming a liquid consisting of two layers of water containing the present solution and the present dispersant in pores (3) a method of injecting into water at a high speed to impinge on a plate to emulsify and disperse;
A method of forcibly passing a liquid consisting of a layer through a narrow gap to emulsify and disperse, and (4) a method of emulsifying and dispersing a liquid consisting of two layers of water containing the present solution and the present dispersant using ultrasonic waves. Is raised.

The dispersing machine which can be used in the mechanical dispersion method is, for example, a planet stirrer in the case of the above method (1), and a Gaul in the case of the above method (2).
In the case of the homogenizer, the method (3) includes, for example, a colloid mill.

In preparing the composition of the present invention, the ease of dispersion of the liquid consisting of the two layers of the present solution and the water containing the present dispersant, the viscosity of the dispersion system, the amount of the preparation, and other overall manufacturing steps are determined. By comprehensively examining, one of the above-mentioned production methods can be selected. In the present application, the phase inversion method is a method in which a water-in-oil emulsion is first prepared, and then the emulsion is phase-inverted to an oil-in-water emulsion to emulsify and disperse the present solution in water. In the production of the composition of the present invention, for example, mechanical shear force, the volume median diameter of oil droplets generated by the production conditions such as the concentration of the dispersant changes,
From the viewpoint of efficacy and stability, the volume median diameter of the oil droplets of the composition of the present invention is usually 0.1 to 50 μm, preferably 0.3 to 50 μm.
The production conditions are determined so as to be 40 μm, more preferably 0.5 to 30 μm, and more preferably 2 to 25 μm.

The composition of the present invention may vary depending on weather conditions, treatment time, treatment method, soil conditions, target pests, etc., but the application amount of the present compound, which is usually an active ingredient, is preferably 1 to 1,000 g per hectare, preferably Becomes 50-500g,
And it is diluted with water and sprayed so that the spraying amount is 10 to 10,000 liters per hectare. These application rates and application rates vary depending on the application time, application place, type of pest, damage status, and the like, and can be increased or decreased without being affected by the above range. Also, the composition of the present invention can be diluted with water and sprayed on the air, for example, by a helicopter, an airplane, or a radio-controlled helicopter.

When the composition of the present invention is used, if necessary, other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, insect growth regulators, fertilizers. , A soil conditioner, a synergist, an adjuvant and the like.

The pests which the composition exhibits a controlling effect include:
For example, the following are mentioned. Hemiptera pests include brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), and brown planthopper (Sogatella f.)
urcifera), grasshopper leafhopper (Nephotetti
x cincticeps), Leafhopper (Nephotetti)
x virescens) etc., leafhoppers, aphids, stink bugs, whiteflies, scale insects, insects,
Lice and the like.

As a pest of Lepidoptera, Chilo sup
pressalis), Cleoptera (Cnaphalocrosic medinali)
s), European Corn Borer (Ostrinia nubilali)
s), Shibattoga (Parapediasia teterrella), Cotton stalk (Notarcha derogata), Swordfish (Plodia)
interseptums such as interpunctella;
ptera litura), Spodoptera exigu
a), Egyptian cotton leaf worm (Spodoptera li
ttoralis), armyworm (Pseudalitia separata), armyworm (Mamestra brassicae), and Tamanayaga (Agrotis ipsil)
on), Trichoplusia spp., Heliothis spp., Helicovepa (Helicove)
nopa (Pieris rapae)
crucivora) and other white butterflies,
oxophyes spp.), Nashihimesui (Grapholita mole)
sta), codling moss (Cydia pomonella) and the like, toads and moss (Carposina niponensis) and the like, the moth moths such as the genus Rionetia, the genus Limantria (Lymantria spp.), and the genus Euproctis (Euproctis)
spp.), stag beetles such as diamondback moth (Plutella xylostella), and cotton beetle (Pectinophora gossypiella)
Kibaga, etc., American White Star (Hyphantria cunea)
Triggers, Iga (Tinea translucens), Koiga (T
ineola bisselliella) and the like.

As dipteran pests, house mosquitoes such as Culex pipiens and Culex pipiens, Aedes albopictus such as Aedes albopictus, Aedes albopices such as Aedes albopictus, Anopheles such as Ceratopodium serrata, houseflyes such as Musca domestica, house flies such as housefly, and a house fly, Musca domestica Examples include flies, flies and flies, such as fly and onion flies, and fruit flies, flies, flies, flies, and flies.

As the insect pests of the order Coleoptera, corn rootworms such as western corn rootworm and southern corn rootworm, scarab beetles such as douganebuui and himekogane, weevil such as weevil, rice weevil, adzuki weevil, beetle beetle, and beetle Epilacna spp. (Epilachna spp.), Such as beetles such as beetles, beetles beetles, leaf beetles, and beetle beetles;
Pleurotus beetles, Nagatus beetles, Longicorn beetles, Aoba sari beetles, and the like.

[0059] Examples of insects of the order of the order Aptera include German cockroaches, black cockroaches, brown cockroaches, brown cockroaches, and German cockroaches. As the insects of the order Thysanoptera, Thrips palmi, Thrips palmi, Thrips palmi, Thrips palmi may be mentioned. Hymenoptera pests include ants, hornets, wasps, and wasps such as wasps.

As the insect pests of the order Orthoptera, there may be mentioned mushrooms and grasshoppers. The flea of the order Lepidoptera includes human fleas and the like.
The louse pests include human lice and lice. Isoptera pests include Yamato termites, house termites and the like. Examples of the mites include plant parasitic mites such as spider mites, mandarin spider mites, red mite spider mites, and red spider mites, animal parasitic mites such as Oxodid tick, and house dust mites.

[0061]

EXAMPLES The present invention will be described in more detail with reference to formulation examples and test examples, but the present invention is not limited to the following examples.

Formulation Example 1 Compound (A)

Embedded image 100 g, IP Solvent 2835 (Idemitsu Petrochemical's isoparaffin-based solvent) 100 g, and Vinicizer 4
A solution was prepared by uniformly mixing 100 g of 0 (an ester solvent manufactured by Kao). 6.25% by weight of polyvinyl alcohol [Gohsenol GL-05 (Gohseno) containing 2 g of TSA730 (an antifoaming agent manufactured by Toshiba Silicone Co., Ltd.)
l), Nippon Gosei Chemical's polyvinyl alcohol (1% by weight)
Surface tension of aqueous solution: 45 dyne / cm)] aqueous solution 32
0 g; K. Using an auto homomixer (homogenizer manufactured by Tokushu Kika Kogyo Co., Ltd.) at room temperature for 4500 rpm /
For 5 minutes to obtain a slurry. 1 g of Xanthan gum and aluminum silicate 2 were added to the obtained slurry.
380 g of an aqueous solution containing 1 g of Biohope L (preservative, manufactured by Kei-I Kasei Co., Ltd.) was added to obtain an oil-in-water emulsion composition having a volume median diameter of 10 μm containing 10% by weight of compound (A).

Formulation Example 2 A solution was prepared by uniformly mixing 100 g of the compound (A), 130 g of naphthesol M (a paraffin-based solvent manufactured by Nippon Petrochemical), and 70 g of Vinicizer 40 (an ester-based solvent manufactured by Kao) as a solvent. This solution is TSA730
6.25% by weight aqueous solution of polyvinyl alcohol containing 2 g (same as that used in Formulation Example 1). K. 450 at room temperature using an auto-homomixer
The mixture was dispersed and stirred at 0 rpm for 5 minutes to obtain a slurry. To the obtained slurry, 380 g of an aqueous solution containing 1.2 g of xanthan gum, 2.4 g of aluminum silicate and 1 g of Biohope L was added, and an oil-in-water emulsion having a median diameter of 10 μm containing 10% by weight of compound (A) was added. A composition was obtained.

Formulation Example 3 A solution was prepared by uniformly mixing 100 g of the compound (A) and 200 g of Hisol SAS-296 (aromatic solvent manufactured by Nippon Petrochemical). A 6.25% by weight aqueous solution of polyvinyl alcohol containing 2 g of TSA730 (Formulation Example 1)
320 g). K. Using an auto homomixer, the mixture was dispersed and stirred at room temperature at 4500 rpm for 5 minutes to obtain a slurry. In the obtained slurry,
Xanthan gum 1.5g, aluminum silicate 3g,
380 g of an aqueous solution containing 1 g of Biohope L and 50 g of propylene glycol were added to obtain an oil-in-water emulsion composition having a volume median diameter of 10 μm containing 10% by weight of the compound (A).

Formulation Example 4 Compound (A) 100 g, Naphthesol M (Nippon Petrochemical's paraffin-based solvent) 145 g, Hysol SAS-
A solution was prepared by uniformly mixing 55 g of 296 (aromatic solvent manufactured by Nippon Petrochemical). This solution was added to TSA730 2
g of a 6.25% by weight aqueous solution of polyvinyl alcohol (same as that used in Formulation Example 1)
T. K. Using an auto homomixer, the mixture was dispersed and stirred at room temperature at 4500 rpm for 5 minutes to obtain a slurry. An aqueous solution 3 containing 1.2 g of xanthan gum, 2.4 g of aluminum silicate, and 3 g of Biohope L was added to the obtained slurry.
80 g was added to obtain an oil-in-water emulsion composition having a volume median diameter of 10 μm containing 10% by weight of the compound (A).

Formulation Example 5 Compound (A) 100 g, isopropyl myristate 20
A solution in which 0 g was uniformly mixed was prepared. Transfer this solution to TS
A. A730 in 320 g of a 6.25% by weight aqueous solution of polyvinyl alcohol (same as that used in Preparation Example 1) containing 2 g of T.A. K. 4 at room temperature using auto homomixer
The slurry was dispersed and stirred at 500 rpm for 5 minutes to obtain a slurry.
To the obtained slurry, 380 g of an aqueous solution containing 1.5 g of xanthan gum, 3 g of aluminum silicate and 1 g of biohope L was added, and an oil-in-water emulsion composition containing 10% by weight of compound (A) and having a median diameter of 10 μm was obtained. Obtained.

Formulation Example 6 Compound (A) 100 g, Naphthesol M (Nippon Petrochemical's paraffin solvent) 130 g, and Vinicizer 4
A solution was prepared by uniformly mixing 70 g of 0 (an ester solvent manufactured by Kao). A 6.25% by weight aqueous solution of polyvinyl alcohol containing 2 g of TSA730 (Formulation Example 1)
320 g). K. Using an auto homomixer, the mixture was dispersed and stirred at room temperature at 4500 rpm for 5 minutes to obtain a slurry. In the obtained slurry,
Xanthan gum 0.5g, aluminum silicate 1.0
g, 380 g of an aqueous solution containing 1 g of Biohope L,
Volume median diameter 10 μm containing 10% by weight of compound (A)
Of an oil-in-water emulsion composition was obtained.

Test Example 1 Insecticidal test against Spodoptera litura The compositions of the present invention obtained in Formulation Examples 1 to 5 were diluted with water (prepared at concentrations of 1.25, 2.5 and 5 ppm, respectively).
And spreading agent (special linole: manufactured by Nippon Agrochemical Co., Ltd.)
Was added to 1/5000 amount of the diluted solution to prepare a test spray solution. Each spray liquid for this test was applied to cabbage seedlings planted in polyethylene cups in a sufficient amount (approximately 50
ml / 2 seedlings). This was air-dried indoors, and one cabbage leaf was cut off.
It was put in a polyethylene container with its head, covered, and stored in a room at 25 ° C. Four days later, the number of live insects and the number of dead insects were examined, and the LC50 value (50% half-lethal concentration) was determined. Table 1 shows the results.

[0069]

[Table 1]

Test Example 2 Residual activity test on Spodoptera litura The compositions of the present invention obtained in Formulation Examples 2, 3, and 6 were diluted with water (prepared to a concentration of 12.5 ppm), and further spread with a spreading agent (special Rino: Japan 1/50 of the diluted solution
The test spraying liquid was prepared by adding 00 amount. This test spray solution was sprayed on a cabbage seedling planted in a polyethylene cup with a spray gun in a sufficient amount (about 50 ml / 2 seedling). This was air-dried indoors and stored in a greenhouse. On the day of the treatment and 6 days after the treatment, one cabbage leaf was cut out, placed in a polyethylene container together with 10 third instar larvae of the cutworm, Spodoptera litura, closed and stored in a room at 25 ° C. Four days after the release, the number of surviving insects and the number of dead insects (including writhing insects) were examined, and the insecticidal rate was determined. Table 2 shows the results.

[0071]

[Table 2]

[0072]

The present invention provides an excellent insecticidal / miticidal composition.

 ──────────────────────────────────────────────────続 き Continuing on the front page F term (reference) 4C055 AA01 BA02 BA42 BB08 CA02 CA13 DA01 4H011 AC01 AC04 BA01 BB09 BC01 BC06 BC18 BC19 DA16 DC05 DD03 DE15 DH02 DH10 4J002 AB04W AB05W AB05X AH00W BE02W BE04W BG01JBW01X01 EA067 EH097 EH147 EL106 EU026 EU046 EU056 EU076 EU116 EU136 EU166 EU176 EU226 EV326 FD180 FD186 FD200 FD310 GB00

Claims (6)

[Claims] (1) Formula (a)Wherein Z is an oxygen atom, a sulfur atom or NR^FourGroup (here
And R^FourIs a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
Represents And Y represents an oxygen atom, a sulfur atom or N
H represents a group, X is each independently a chlorine atom or
Represents a bromine atom; ^Two, R^ThreeAnd R^TenAre independent of each other
A halogen atom, a haloalkyl group having 1 to 3 carbon atoms or
Represents an alkyl group having 1 to 3 carbon atoms, and t is an integer of 0 to 2
Represents a number, R ¹Is the formulaIn the formula, A represents an optionally substituted heterocyclic group. B is
Oxygen atom, S (O) q group, NR⁹Group, C (= G¹) G^TwoBase
Or G¹C (= G^Two) Represents a group, and q is an integer of 0 to 2.
Represents, R⁹Is from a hydrogen atom, an acetyl group or a carbon number 1
3 represents an alkyl group;¹And G^TwoAre independent
Represents an oxygen atom or a sulfur atom;^Five, R⁶, R⁷,
R¹¹And R¹²Are each independently a hydrogen atom, carbon number 1
From 3 to 3 alkyl groups or trifluoromethyl groups
Then R¹³And R¹⁴Are each independently a hydrogen atom,
An alkyl group having a prime number of 1 to 3, a trifluoromethyl group or
Represents a halogen atom, p represents an integer of 0 to 6,
s represents an integer of 1 to 6. Q indicated by｝₁, Q_Two, Q
_Three, Q_Four, Q_Five, Q₆Or Q₇Represents ]
Lopropene compound, (b) Surface in 1% by weight aqueous solution
A dispersant having a tension of 40 dyne / cm or more, (c) 2
The solubility in 100 g of water at 0 ° C. is 1 g or less.
Contains an organic compound that is liquid at room temperature and (d) water
Insecticidal / miticidal composition. 2. Component (a) is 0.1 to 40% by weight, component (b) is 0.1 to 20% by weight, component (c) is 0.5 to component (a). The composition according to claim 1, which is contained in an amount of from 50 to 50 times by weight. 3. The composition according to claim 1, further comprising a viscosity modifier. 4. A method for further adding 0.01 to 10% by weight of a viscosity modifier.
The composition according to claim 2, wherein the composition comprises: 5. Component (a) having the formula: 3,5-dichloro-4- (3- (5-trifluoromethyl-2-pyridyloxy) propyloxy) represented by
The composition according to any one of claims 1 to 4, which is -1- (3,3-dichloro-2-propenyloxy) benzene. 6. A method for killing insects and mites, comprising applying the composition according to any one of claims 1 to 5 to a place where a pest or mite inhabits or is likely to inhabit. .