WO2014003084A1 - Microcapsule - Google Patents

Microcapsule Download PDF

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Publication number
WO2014003084A1
WO2014003084A1 PCT/JP2013/067587 JP2013067587W WO2014003084A1 WO 2014003084 A1 WO2014003084 A1 WO 2014003084A1 JP 2013067587 W JP2013067587 W JP 2013067587W WO 2014003084 A1 WO2014003084 A1 WO 2014003084A1
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WO
WIPO (PCT)
Prior art keywords
component
weight
microcapsule
present
trade name
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2013/067587
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English (en)
French (fr)
Inventor
Kazuyuki Yanagisawa
Motofumi Mizutani
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Priority to EP13810663.8A priority Critical patent/EP2863742B1/en
Priority to ES13810663T priority patent/ES2744497T3/es
Priority to JP2014561626A priority patent/JP2015521585A/ja
Priority to AU2013281755A priority patent/AU2013281755B2/en
Priority to BR112014031664A priority patent/BR112014031664A2/pt
Priority to US14/411,181 priority patent/US20150173351A1/en
Priority to CN201380033282.9A priority patent/CN104411169B/zh
Publication of WO2014003084A1 publication Critical patent/WO2014003084A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • A01N25/28Microcapsules or nanocapsules
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/22Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/42Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/16Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to a microcapsule in which photodegradation of an agriculturally active ingredient has been inhibited.
  • Patent Document 1 JP 11-504030 W
  • An object of the present invention is to provide a new microcapsule in which photodegradation of an agriculturally active ingredient has been inhibited.
  • the present inventors have intensively been studied so as to find a microcapsule in which photodegradation of an agriculturally active ingredient has been inhibited, and found that, in a microcapsule comprising:
  • component a an agriculturally active ingredient in which a retention rate is less than 50% after irradiation with xenon light (290 nm cutoff) at an intensity of 0.68 W/m 2 at 340 nm for 8 hours
  • component b a hydrophobic organic solvent
  • the present invention includes the followings:
  • a microcapsule comprising:
  • a weight ratio of the agriculturally active ingredient to the hydrophobic organic solvent is from 10:90 to 70:30.
  • hydrophobic organic solvent (s) is/are one or more hydrophobic organic solvent (s) selected from the group consisting of esters, ketones, aromatic hydrocarbons, and paraffins .
  • microcapsule of the present invention (hereinafter sometimes referred to as a microcapsule of the present invention) is a microcapsule containing an agriculturally active ingredient which is significantly unstable against light, such as the component a, and is a microcapsule which can effectively inhibit photodegradation of the
  • xenon light means a light source in which a gas filled in a tube is xenon. Usually, xenon light means uniquely the same spectrum.
  • Xenon light (290 nm cutoff) means xenon light having a wavelength within a range of 290 nm or more, and xenon light passed through a
  • borosilicate filter corresponds to this.
  • a method for the calculation of a retention rate of the agriculturally active ingredient defined above is more specifically as follows. First, 250 mg of the agriculturally active ingredient is dissolved in 50 mL of a solvent such as acetone, which can sufficiently dissolve the agriculturally active ingredient and also has high volatility, and 1 mL of the solution is added to a glass petri dish having a diameter of 6 cm using a one-mark pipette, spread entirely over the petri dish, and then air-dried at room temperature. The petri dish is covered with a lid made of quartz glass and then set in a weathering tester (manufactured by Q-Lab).
  • a solvent such as acetone
  • the amount of the agriculturally active ingredient remaining on the petri dish is determined by a known determination method such as high-performance liquid chromatography. It is possible to determine a retention rate by calculating as the weight percentage relative to 5 mg of the agriculturally active ingredient used above.
  • the above agriculturally active ingredient used in the microcapsule of the present invention may be any of an
  • insecticidally active component a fungicidally active
  • the agriculturally active ingredient includes fenpyrazamine, allethrin, and prallethrin.
  • the retention rates of fenpyrazamine, allethrin, and prallethrin after irradiation with xenon light (290 nm cutoff) at an intensity of 0.68 /m 2 at 340 nm for 8 hours according to the method for calculation above-mentioned, are 28.1%, 3.3% and 6.4%, respectively.
  • the microcapsule of the present invention usually contains a component a in the total amount of 1 to 80% by weight, and preferably 10 to 70% by weight.
  • component b means an organic solvent which is liquid at normal temperature (25°C) and is immiscible in water.
  • an organic solvent having water solubility of 20% by weight or less at 25°C is used.
  • the hydrophobic organic solvent include hydrophobic organic solvents such as vegetable oils, esters, ketones, aromatic hydrocarbons, and paraffins, for example, the following hydrophobic organic solvents:
  • Vegetable oils rapeseed oil, soybean oil, linseed oil, corn oil, and olive oil;
  • Esters diisobutyl adipate, diisodecyl adipate, dialkyl phthalate (didecyl phthalate, etc.), octyl oleate, lauryl oleate, octyldodecyl oleate, and isopropyl myristate;
  • Ketones methyl isobutyl ketone, heptanone, octanone, nonanone, cyclohexanone and acetophenone;
  • Aromatic hydrocarbons toluene, xylene,
  • methylnaphthalene, dimethylnaphthalene, triisopropylbiphenyl and dimethylisopropylnaphthalene methylnaphthalene, dimethylnaphthalene, triisopropylbiphenyl and dimethylisopropylnaphthalene .
  • aromatic hydrocarbon solvents can be used as aromatic hydrocarbon solvents.
  • hydrocarbons examples of the commercially available
  • aromatic hydrocarbon solvents include Hisol SAS-296 (mixture of 1-phenyl-l-xylylethane and 1-phenyl-l-ethylphenylethane, trade name of JX Nippon Oil & Energy Corporation) , Hisol SAS- LH (trade name of JX Nippon Oil & Energy Corporation) , CACTUS SOLVENT HP-MN (methylnaphthalene 80%, trade name of JX Nippon Oil & Energy Corporation), CACTUS SOLVENT HP-DMN
  • Solvesso 150 aromatic hydrocarbon, trade name of ExxonMobil Chemical Ltd.
  • Solvesso 200 aromatic hydrocarbon, trade name of ExxonMobil Chemical Ltd.
  • Solvesso 150ND aromatic hydrocarbon, trade name of ExxonMobil Chemical Ltd.
  • Solvesso 200ND aromatic hydrocarbon, trade name of
  • Paraf,fins normal paraffin, isoparaffin, cycloparaffin, and liquid paraffin
  • paraffin solvents can be used as paraffins.
  • examples of the commercially available paraffin solvents include NORPAR 13 (normal paraffin, trade name of ExxonMobil Chemical Ltd.),
  • NORPAR 15 normal paraffin, trade name of ExxonMobil Chemical Ltd.
  • ISOPAR E isoparaffin, trade name of ExxonMobil
  • ISOPAR G isoparaffin, trade name of
  • component b used in the microcapsule of the present invention there is no particular limitation on the component b used in the microcapsule of the present invention, and one or more hydrophobic organic solvent (s) selected from the group consisting of esters, ketones, aromatic hydrocarbons, and paraffins is/are preferably used. Of these, aromatic ketones such as acetophenone are more preferably used.
  • a weight ratio of the component a to the component b is from 10:90 to 70:30, and preferably from 30:70 to 70:30.
  • the microcapsule of the present invention usually contains the component b in the total amount of 20 to 95% by weight, and preferably 30 to 90% by weight, based on the entire amount of the microcapsule of the present invention.
  • microcapsule of the present invention further contains one or more UV protectants.
  • UV protectants examples include benzophenone-based ultraviolet absorbers such as 2 , 4-dihydroxybenzophenone, 2- hydroxy-4-methoxybenzophenone, and 2-hydroxy-4-n-octyl- benzophenone ; benzotriazole-based ultraviolet absorbers such as 2- (2-hydroxy-5-methylphenyl) benzotriazole , 2- [2-hydroxy-3- (3,4,5, 6-tetrahydrophthalimide-methyl ) -5- methylphenyl] benzotriazole, 2- ( 3-tert-butyl-2-hydroxy-5- methylphenyl) -5-chlorobenzotriazole, 2- (2-hydroxy-5-tert- octylphenyl) benztriazole, and 2- (2-hydroxy-3, 5-di-tert- pentylphenyl) benzotriazole; benzoate-based ultraviolet absorbers such as 2 , 4-di-tert-butylphenyl 3 , 5-di-tert-butyl-
  • UV protectant used in the microcapsule of the present invention, and it is preferred to use a UV protectant which is miscible in the component b.
  • the total content is usually from 1 to 50% by weight, and preferably from 3 to 35% by weight, based on the entire amount of the microcapsule of the present invention, .
  • microcapsule of the present invention is a
  • microcapsule in which liquid droplets containing a component a, a component b, and more preferably a component c are coated with a resin.
  • the component a is suspended or
  • a film in the microcapsule of the present invention is formed from the resin.
  • the resin includes, for example, thermosetting resins such as a polyurethane resin, a polyurea resin, a urea-formalin resin, a melamine-urea resin, and a phenol-formalin resin.
  • a polyurethane resin or a polyurea resin is preferably used.
  • a resin which forms a film of the microcapsule of the present invention is usually a resin obtained by reacting polyisocyanate with polyol or polyamine.
  • the polyisocyanate includes, for example, hexamethylene diisocyanate, adduct of hexamethylene diisocyanate and trimethylolpropane, biuret condensate of three molecules of hexamethylene diisocyanate, adduct of tolylene diisocyanate and trimethylolpropane, isocyanurate condensate of tolylene diisocyanate, isocyanurate condensate of hexamethylene diisocyanate, isocyanurate condensate of isophorone
  • isocyanate prepolymer in which one isocyanate moiety of hexamethylene diisocyanate composes isocyanurate together with two molecules of tolylene diisocyanate, and the other isocyanate moiety composes isocyanurate together with two molecules of the other hexamethylene diisocyanate, 4,4'- methylenebis (cyclohexyl isocyanate), and trimethyl
  • the amount of the polyisocyanate used in the present invention is usually determined depending on the amount of the film of the obtained microcapsule.
  • the amount of the film of the obtained microcapsule is usually from 0.1 to 40% by weight, and preferably from 0.2 to 30% by weight, based on the entire amount of the obtained microcapsule.
  • the amount of the polyisocyanate used in the present invention is
  • the polyol includes, for example, ethylene glycol, propylene glycol, butylene glycol, and cyclopropylene glycol.
  • the polyamine includes, for example, ethylenediamine, hexamethylenediamine, diethylenetriamine , and
  • the amount of the polyol or polyamine used in the present invention is usually determined depending on the amount of the film of the obtained microcapsule.
  • the amount of the polyol used in the present invention is usually from 1 to 80% by weight, and preferably from 3 to 60% by weight, based on the amount of the film of the microcapsule.
  • the amount of the polyamine used in the present invention is usually from 1 to 40% by weight, and preferably from 3 to 20% by weight, based on the amount of the film of the
  • microcapsule microcapsule
  • a method for producing the microcapsule of the present invention (hereinafter sometimes referred to as a present production method) will be described, but the present
  • the present production method includes the following first to third steps.
  • the first step of the present production method is the step of suspending or dissolving a component a in a component b to prepare a suspension or a solution of the component a.
  • the component a is suspended or dissolved in the component b.
  • the component a is a component a which is solid at normal temperature (25°C) (hereinafter sometimes referred to as a solid component a)
  • a suspension hereinafter sometimes referred to as a present suspension a
  • the present suspension a can be prepared by finely grinding the solid component a in the component b using a wet grinding mill such as a beads mill. It is also possible to prepare by finely grinding the solid component a with or without adding other components using a dry grinding mill such as a jet mill, and adding the thus obtained finely ground powder to the component b.
  • the solution in which a component a is dissolved in a component b can be prepared by dissolving the component a in the component b
  • the first step includes the step of
  • the component a and the component c take any one of the following forms (1) to (4) .
  • Both the component a and the component c are suspended in the component b.
  • the solid component a can take the form (1) or (2) depending on solubility of the solid component a in the component b and a weight ratio of the solid component a to the component b.
  • the component c is a component c which is solid at normal temperature (25°C) (hereinafter sometimes referred to as a solid component c)
  • the component c can take the form (1) or (3) depending on solubility of the solid component c to the component b and a weight ratio of the solid component c to the component b.
  • Suspensions of (1) to (3) can be prepared by the same operation as in a method for preparing the present suspension a.
  • the solid component a and the solid component c may be finely milled at the same time by a wet grinding mill or a dry grinding mill, or the present suspension a and a suspension in which the solid component c has been suspended in the component b may be separately prepared, followed by mixing, in the method for preparing the present suspension a.
  • the component c is dissolved in the component b and then the solid component a is added to the solution.
  • the component a is dissolved in the component b and then the solid component c is added to the solution.
  • the solution (4) can be prepared by dissolving the component a and the component c in the component b.
  • the resin composing the film is a polyurethane resin or a polyurea resin
  • polyisocyanate is added in advance to the suspension or solution obtained in the first step. It is preferred that the suspension or solution, which is obtained in the first step in which the component a and optionally added component c are suspended or dissolved in the component b, is quickly used in the subsequent step.
  • the second step of the present production method is the step of mixing the suspension or solution obtained in the first step with water to prepare liquid droplets.
  • the amount of water used in the second step is usually within a range of 0.8 to 2 times more than that of the suspension or solution obtained in the first step.
  • Deionized water is preferably used as water used in the second step, and a thickener may be added to water.
  • Examples of the thickener include natural
  • polysaccharides such as gum arabic, xanthan gum, rhamsan gum, locust bean gum, guar gum, carrageenan, welan gum, alginic acid, alginate, and gum tragacanth; vinyl-based polymers such as polyvinyl alcohol, polyvinylpyrrolidone, vinyl acetate copolymer, and sodium polyacrylate; synthetic polymers ' such as polyoxyalkylene; semi-synthetic polymers such as
  • carboxymethyl cellulose carboxymethyl cellulose
  • mineral matter powders such as aluminum silicate, magnesium aluminum silicate, smectite, bentonite, hectorite, synthetic hydrated silicic acid, and dry silica
  • alumina sol It is possible to use, as these thickeners, commercially available products as they are.
  • KELZAN S trade name of CP Kelco, Inc.
  • VEEGUM xanthan gum
  • Granules (trade name of Vanderbilt Company, Inc.) as aluminum silicate, and Aerosil 200 (trade name of Evonik Degussa).
  • the method for preparing liquid droplets in water includes, for example, a method in which water is added to the suspension or solution obtained in the first step, followed by stirring using a stirrer.
  • stirrer used in this case includes, for example, a propeller stirrer, a turbine stirrer, and a high-speed shear stirrer.
  • the stirrer include T.K. Homo Mixer, T.K. Homomic Line Flow, T.K. Pipeline Homo Mixer, and T.K. Filmix manufactured by PRIMIX Corporation; CLEARMIX manufactured by M Technique Co., Ltd.; POLYTRON homogenizer and MEGATRON homogenizer manufactured by KINEMATICA AG; and SUPRATON manufactured by Tsukishima Kikai Co., Ltd.
  • liquid droplets are
  • a microcapsule with a film formed of a polyurethane resin is obtained.
  • polyamine is added, a microcapsule with a film formed of a polyurea resin is
  • the polyol or polyamine may be added before
  • the third step is the step of forming a film of a resin around the liquid droplets obtained in the second step.
  • polyisocyanate is dissolved in the component b.
  • polyisocyanate contained in the liquid droplets react with polyol or polyamine existing in water at an
  • the resin composing the film is a polyurethane resin
  • a water dispersion of the liquid droplets obtained in the second step is heated at 40 to 80°C under stirring, followed by maintaining for 0.5 to 48 hours,
  • the resin composing the film is a polyurea resin
  • the pH of a water dispersion of the liquid droplets is adjusted within a range of neutral to weak alkaline, followed by maintaining at 0 to 60°C for about 0.5 to 48 hours, whereby, a film of the polyurea resin is formed around the liquid droplets.
  • An average particle diameter of the microcapsule of the present invention is almost the same as that of liquid
  • the average particle diameter of liquid droplets prepared in the second step and that of the microcapsule of the present invention are usually from 5 to 60 ⁇ , preferably from 10 to 50 ym, and more
  • the average particle diameter means a volume median diameter.
  • the volume median diameter refers to a particle diameter at which a cumulative frequency in a volume equivalent frequency distribution is to be 50%, and the volume median diameter can be determined, for example, by wet measurement using a laser diffraction particle size distribution measuring apparatus. More specifically, liquid droplets or microcapsules are dispersed in water and then the volume median diameter is measured using the apparatus. The laser diffraction particle size distribution measuring
  • apparatus includes, for example, Mastersizer 2000
  • the microcapsule of the present invention is obtained as a composition in the form of an aqueous suspension.
  • microcapsule of the present invention obtained by the present production method can be used as a powder
  • composition in the form of an aqueous suspension of the microcapsule of the present invention obtained by the present production method pesticide auxiliary agents which are used in a conventional pesticidal composition in the form of an aqueous suspension is added, whereby, it is possible to use as a pesticidal composition in the form of an aqueous suspension in which the microcapsule of the present invention is suspended in an aqueous continuous phase (hereinafter sometimes referred to as a composition of the present
  • the microcapsule of the present invention obtained by the present production method is used, for example, as a pesticidal composition in the form of an aqueous suspension, containing the component a in the amount of 0.5 to 25% by weight based on the entire amount of the composition of the present invention.
  • pesticide auxiliary agents which may be contained in the composition of the present invention include surfactants, thickeners, defoamers, preservatives,
  • surfactants examples include nonionic surfactants
  • nonionic surfactant examples include polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene lanolin alcohol, polyoxyethylene alkyl phenol formalin condensate, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glyceryl monofatty acid ester, polyoxypropylene glycol monofatty acid ester,
  • polyoxyethylene sorbitol fatty acid ester polyoxyethylene castor oil derivative, polyoxyethylene fatty acid ester, higher fatty acid glycerol ester, sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene polyoxypropylene block polymer, polyoxyethylene fatty acid amide, alkylol amide, polyoxyethylenealkylamine, and polyoxyethylene
  • alkanediol examples include butanediol.
  • cationic surfactants include
  • alkylamine hydrochlorides such as dodecylamine hydrochloride
  • alkyl quaternary ammonium salts such as dodecyltrimethyl ammonium salt, alkyldimethylbenzyl ammonium salt,
  • alkylpyridinium salt alkylisoquinolinium salt
  • dialkylmorpholinium salt dialkylmorpholinium salt
  • benzethonium chloride dialkylmorpholinium salt
  • surfactants include fatty acid sodium such as sodium
  • sodium ether carboxylate such as sodium
  • condensates of higher fatty acid such as sodium lauroyl sarcosine and sodium N-lauroyl glutamate; higher fatty acid ester sulfonates such as higher alkyl sulfonate and lauric acid ester sulfonic acid salt; dialkyl sulfosuccinates such as dioctyl sulfosuccinate ; higher fatty acid amide sulfonates such as oleic acid amide sulfonic acid; alkyl aryl sulfonates such as sodium dodecylbenzene sulfonate and diisopropyl naphthalene sulfonate; higher alcohol sulfuric acid ester salts such as formalin condensate of alkyl aryl sulfonate and pentadecane-2-sulfate ; polyoxyethylene alkyl phosphate esters such as dipolyoxyethylene dodecyl ether phosphate;
  • amphoteric surfactants include N- laurylalanine, N, N, N-trimethylaminopropionic acid, ⁇ , ⁇ , ⁇ - trihydroxyethylaminopropionic acid, N-hexyl-N, N- dimethylaminoacetic acid, 1- ( 2-carboxyethyl ) pyridinium
  • the total content is usually from 0.1 to 20% by weight, and preferably from 0.5 to 10% by weight, based on the entire amount of the composition of the present invention.
  • thickeners examples include those exemplified previously.
  • the total content is usually from 0.01 to 10% by weight, and preferably from 0.1 to 5% by weight, based on the entire amount of the composition of the present invention.
  • Examples of the defoamer include silicone-based
  • defoamers such as AN I FOAM C EMULSION (trade name of Dow).
  • TSA730 (trade name of MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC)
  • TSA731 (trade name of
  • MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC TSA732 (trade name of MOMENTIVE PERFORMANCE MATERIALS JAPAN LLC), and YMA6509 (trade name of OMENTIVE PERFORMANCE MATERIALS JAPAN LLC) ; and fluorine-based defoamers such as Fluowet PL80
  • the total content is usually from 0.01 to 3% by- weight, and preferably from 0.05 to 1% by weight, based on the entire amount of the composition of the present invention.
  • preservative examples include p-hydroxybenzoic acid ester, salicylic acid derivative, proxel (1,2- benzisothiazolin-3-one) , and isothiazolin-3-one derivative (for example, BIOHOPE L (trade name of KI Chemical Industry Co. , Ltd. ) ) .
  • composition of the present invention contains the preservative
  • the total content is usually from 0.01 to
  • antifreezing agent examples include water- soluble glycols such as ethylene glycol and propylene glycol.
  • the total content is usually from 0.5 to 30% by weight, and preferably from 1 to 20% by weight, based on the entire amount of the composition of the present invention .
  • pH adjustor examples include citric acid monohydrate, sorbic acid, potassium sorbate, disodium
  • the total content is usually from 0.01 to 5% by weight, and preferably from 0.5 to 3% by weight, based on the entire amount, of the composition of the present invention.
  • water used in the composition of the present invention there is no particular limitation on water used in the composition of the present invention, and it is possible to use water used in a conventional pesticidal composition in the form of an aqueous suspension, such as tap water, well water, and deionized water.
  • composition of the present invention usually contains
  • composition of the present invention can be applied to places such as paddy fields, cultivated lands, orchards, grass plot, and non-agricultural lands in the same manner as in the case of a conventional pesticidal composition in the form of an aqueous suspension.
  • the composition of the present invention can be applied to places such as paddy fields, cultivated lands, orchards, grass plot, and non-agricultural lands in the same manner as in the case of a conventional pesticidal composition in the form of an aqueous suspension.
  • the present invention is optionally diluted with water and then the obtained water dilution can be applied by a method in which the composition is applied to plants growing in the above places or the soil in the above places.
  • the method for applying the water dilution include a soil surface application or foliage application method of the water dilution using a known sprinkler.
  • composition of the present invention can be applied as it is without being diluted with water and, for example, the composition of the present invention is applied along from levee to levee of paddy fields under flooding. Before application, the composition of the present invention is usually mixed by slightly shaking a vessel containing the composition of the present invention.
  • Fenpyrazamine was dry-milled by a vertical type jet mill ( JOM-0101-type jet mill, manufactured by Seishin Enterprise Co., Ltd.) to prepare fenpyrazamine fine powders having an average particle diameter of 5 ⁇ or less.
  • composition of a microcapsule containing fenpyrazamine composition of a microcapsule containing fenpyrazamine .
  • a microcapsule containing fenpyrazamine had an average particle diameter of 40.1 , ⁇ .
  • Example 1 except that the amount of the fenpyrazamine fine powders prepared in Preparation Example 1 was changed from 10 parts by weight to 5 parts by weight, and the amount of the aromatic hydrocarbon (the same as mentioned above) was
  • composition (2) of the present invention containing 5% by weight of fenpyrazamine was obtained.
  • a microcapsule containing fenpyrazamine had an average particle diameter of 44.1 ⁇ .
  • the composition (3) of the present invention containing 10% by weight of fenpyrazamine was obtained.
  • the composition (4) of the present invention containing 10% by weight of fenpyrazamine was obtained.
  • Example 1 except that diisobutyl adipate (manufactured by Kao Corporation under the trade name of Vinisizer 40) was used in place of the aromatic hydrocarbon (the same as mentioned above) , the composition (5) of the present
  • a microcapsule containing fenpyrazamine had an average particle diameter of 33.2 pm.
  • Example 1 except that acetophenone (manufactured by ako Pure Chemical Industries, Ltd. ) was used in place of the aromatic hydrocarbon (the same as mentioned above) , and the average particle diameter of the microcapsule containing fenpyrazamine was changed from 40.1 im to 13.3 ⁇ by
  • the composition (6) of the present invention containing 10% by weight of fenpyrazamine was obtained.
  • ultraviolet absorber manufactured by BASF Corporation under the trade name of Tinuvin 571
  • aqueous polyvinyl alcohol solution emulsifying the fenpyrazamine suspension in the aqueous polyvinyl alcohol solution to obtain a fenpyrazamine emulsion.
  • aqueous 1.1% by weight diethylenetriamine (the same as mentioned above) solution was added, followed by stirring at 60°C for 3 to 4 hours to obtain an aqueous suspension composition of a microcapsule containing fenpyrazamine .
  • Preparation Example 1 15 parts by weight of water and 65 parts by weight of the above aqueous suspensinon composition were mixed together to obtain the composition (7) of the present invention, containing 10% by weight of fenpyrazamine .
  • a microcapsule containing fenpyrazamine had an average particle diameter of 32.0 ⁇ .
  • composition (8) of the present invention containing 10% by weight of
  • allethrin A microcapsule containing allethrin had an average particle diameter of 12.0 ⁇ .
  • the composition (9) of the present invention containing 5% by weight of allethrin was obtained.
  • microcapsule containing etoc was changed from 12.0 ⁇ to 30.6 ⁇ by adjusting a stirring force using the rotor-stator homogenizer (the same as mentioned above), the composition (10) of the present invention, containing 10% by weight of prallethrin was obtained.
  • Example 10 except that the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 12.4 ⁇ by adjusting a stirring force using the rotor- stator homogenizer (the same as mentioned above) , the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 12.4 ⁇ by adjusting a stirring force using the rotor- stator homogenizer (the same as mentioned above) , the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 12.4 ⁇ by adjusting a stirring force using the rotor- stator homogenizer (the same as mentioned above) , the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 12.4 ⁇ by adjusting a stirring force using the rotor- stator homogenizer (the same as mentioned above) , the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 12.4 ⁇ by
  • composition (11) of the present invention containing 10% by weight of prallethrin was obtained.
  • Example 10 except that the average particle diameter of the microcapsule containing prallethrin was changed from 30.6 ⁇ to 5.9 ⁇ by adjusting a stirring force using the rotor- stator homogenizer (the same as mentioned above) , the
  • composition (12) of the present invention containing 10% by weight of prallethrin was obtained.
  • compositions (1) to (12) of the present invention were respectively diluted with water so as to make each active ingredient concentration to 1,120 ppm.
  • Each of the dilutions (100 L) was added to a glass petri dish having a diameter of 6 cm, uniformly spread and then air-dried at room temperature.
  • the petri dish was covered with a lid made of quartz glass and placed in a weathering tester (manufactured by Q-Lab Corporation under the trade name of Q-SUN Xenon Accelerated Weathering Tester, Model Xe-3) equipped with a borosilicate filter (manufactured by Q-Lab Corporation under the trade name of Daylight-BB Optical Filter) attached thereto, followed by irradiation with xenon light under the conditions of an intensity at 340 nm of 0.68 W/m 2 and a temperature of 34 °C (34 °C as measured by an insulated black panel thermometer) for 6 hours. After irradiation,
  • fenpyrazamine remaining on the petri dish was extracted with acetonitrile, followed by quantitative analysis through high- performance liquid chromatography or gas chromatography. A retention rate was determined by calculating as the weight percentage relative to the amount of fenpyrazamine, allethrin or prallethrin before irradiation.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
PCT/JP2013/067587 2012-06-26 2013-06-20 Microcapsule Ceased WO2014003084A1 (en)

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EP13810663.8A EP2863742B1 (en) 2012-06-26 2013-06-20 Microcapsule
ES13810663T ES2744497T3 (es) 2012-06-26 2013-06-20 Microcápsula
JP2014561626A JP2015521585A (ja) 2012-06-26 2013-06-20 マイクロカプセル
AU2013281755A AU2013281755B2 (en) 2012-06-26 2013-06-20 Microcapsule
BR112014031664A BR112014031664A2 (pt) 2012-06-26 2013-06-20 microcápsula
US14/411,181 US20150173351A1 (en) 2012-06-26 2013-06-20 Microcapsule
CN201380033282.9A CN104411169B (zh) 2012-06-26 2013-06-20 微胶囊

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CN105548442A (zh) * 2016-01-30 2016-05-04 郭庆龙 一种胺苯吡唑酮残留量的gc-ms/ms快速测定方法
EP2962562A4 (en) * 2013-02-28 2016-08-24 Sumitomo Chemical Co SUSPECTED AQUEOUS PESTICIDE COMPOSITION
JP2022167051A (ja) * 2021-04-22 2022-11-04 日本化薬株式会社 マイクロカプセル農薬組成物

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CN105548444A (zh) * 2016-01-30 2016-05-04 郭庆龙 一种胺苯吡唑酮残留量的gc-ms/ms测定方法
CN105510507A (zh) * 2016-01-30 2016-04-20 郭庆龙 一种gc-ms/ms测定果蔬中胺苯吡唑酮残留的方法

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EP2962562A4 (en) * 2013-02-28 2016-08-24 Sumitomo Chemical Co SUSPECTED AQUEOUS PESTICIDE COMPOSITION
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AU2013281755B2 (en) 2016-12-01
JP2015521585A (ja) 2015-07-30
BR112014031664A2 (pt) 2017-06-27
AR091529A1 (es) 2015-02-11
EP2863742A4 (en) 2016-03-30
AU2013281755A1 (en) 2015-01-29
EP2863742A1 (en) 2015-04-29
EP2863742B1 (en) 2019-07-31
CN104411169B (zh) 2017-11-10
ES2744497T3 (es) 2020-02-25
CN104411169A (zh) 2015-03-11

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