Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION 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
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION 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
  • A01N25/00—Biocides, 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
  • A01N25/02—Biocides, 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 liquids as carriers, diluents or solvents
  • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION 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
  • A01N25/00—Biocides, 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
  • A01N25/30—Biocides, 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 characterised by the surfactants
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
  • A01P13/00—Herbicides; Algicides

Definitions

• the present invention relates to a liquid pesticide composition.
• Patent Document 1 may refer to a compound represented by the following formula (I), which is an active ingredient of a herbicide, as a pesticide active ingredient (hereinafter referred to as "Compound (I)"). .)It has been known.
• An object of the present invention is to provide a liquid pesticide composition containing compound (I) and having good emulsion stability when mixed with water.
• the present invention provides the following liquid pesticide compositions.
• [1] One selected from the group consisting of (a) a compound represented by the following formula (I), and (b) butyl propionic acid, benzoic acid ester, dimethyl isosorbide, 2-heptanone, benzyl acetate and butyl biphenyl.
• a liquid pesticide composition containing the above organic solvent [2] The liquid pesticide composition according to [1], which contains a surfactant. [3] The liquid pesticide composition according to [1] or [2], which contains one or more surfactants selected from the group consisting of ionic surfactants and nonionic surfactants.
• liquid pesticide composition (hereinafter, also simply referred to as “liquid pesticide composition”) is It contains (a) compound (I) and (b) one or more organic solvents selected from the group consisting of butyl propionic acid, benzoic acid ester, dimethyl isosorbide, 2-heptanone, benzyl acetate and butyl biphenyl.
• the liquid pesticide composition can be suitably used as a liquid pesticide preparation called an emulsion (EC: Emulsifiable Concentrate) in the field of pesticides.
• the liquid pesticide composition further contains a surfactant, preferably a liquid in which all of the components it contains are completely or almost completely dissolved in an organic solvent. ..
• the liquid pesticide composition can be suitably used as a liquid pesticide preparation called an emulsion oil in water (EW) in the field of pesticides.
• EW emulsion oil in water
• the liquid pesticide composition further contains a surfactant, water, and contains an aqueous phase and oil phase particles dispersed in the aqueous phase.
• the liquid pesticide composition contains compound (I) as a pesticide active ingredient.
• Compound (I) is a known compound and can be produced by a known method such as the method described in US Pat. No. 6,537,948.
• the content of the compound (I) in the liquid pesticide composition is generally 0.01% by mass or more and 30% by mass or less, preferably 0.1% by mass. 25% by mass or less, more preferably 0.5% by mass or more and 20% by mass or less, further preferably 1% by mass or more and 15% by mass or less, still more preferably 2% by mass or more and 10% by mass or less.
• Other preferable ranges of the content are, for example, 3% by mass or more and 15% by mass or less, 3% by mass or more and 10% by mass or less, 3.5% by mass or more and 10% by mass or less, 5% by mass or more and 15% by mass or less, or. It is 5% by mass or more and 10% by mass or less. Adjusting the content of compound (I) within the above range moderately increases the content of compound (I) in the liquid pesticide composition and improves the stability of the emulsion of the liquid pesticide composition. It is suitable for doing so.
• the liquid pesticide composition is at least one selected from the group consisting of butyl propionic acid, benzoic acid ester, dimethyl isosorbide, 2-heptanone, benzyl acetate and butyl biphenyl (hereinafter, also referred to as "group A"). It contains a seed solvent (hereinafter, also referred to as "organic solvent A”). By containing the organic solvent A, a liquid pesticide composition having good emulsion stability when mixed with water can be obtained.
• the benzoic acid ester methyl benzoate, ethyl benzoate, butyl benzoate, and benzyl benzoate are suitable.
• the liquid pesticide composition can contain an organic solvent other than the organic solvent A (hereinafter, also referred to as "organic solvent B").
• organic solvent B an organic solvent other than the organic solvent A
• the content of the organic solvent A is preferably 50% by mass or more, more preferably 60% by mass or more, from the viewpoint of improving the stability of the emulsion. Yes, more preferably 70% by mass or more, still more preferably 80% by mass or more, 100% by mass, or 99% by mass or less.
• the organic solvent B has a water solubility of preferably 20% by mass or less at 25 ° C., for example, 10% by mass or less, 5% by mass or less, or 3% by mass or less. Further, it may be 1% by mass or less.
• the water solubility of the organic solvent B at 25 ° C. is usually 0% by mass or more, and may be 10-5 % by mass or more.
• the water solubility at 25 ° C. means the solubility in water having a temperature of 25 ° C. and a pH of 7.
• a water solubility at 25 ° C. of 10% by mass means that the solubility in 1 g of water having a temperature of 25 ° C. and a pH of 7 is 1 ⁇ 10 -1 g.
• the water solubility of the organic solvent As the water solubility of the organic solvent, the numerical value described in the database (Solubility Database) of the International Union of Pure and Applied Chemistry (IUPAC) or the National Institute of Standards and Technology (NIST) can be adopted. If not listed in the database, the water solubility of the organic solvent can be measured by using high speed liquid chromatography to quantify the saturated solubility in water at a temperature of 25 ° C. and a pH of 7. ..
• organic solvent B for example, Alcohols such as hexanol, heptanol, octanol; Methyl caproate, Methyl caprylate, Methyl caprate, Methyl laurate, Methyl myristate, Methyl palmitate, Methyl stearate, Methyl oleate, Methyl linoleate, Ethyl acetate, Butyl acetate, Hexyl acetate, Octyl acetate, Phytoic acid Esters such as dimethyl, diethyl phthalate, diethyl oxalate, dioctyl succinate, methyl salicylate, dimethyl adipate, dibutyl adipate, tert-butyl acetoacetate and allyl acetoacetate; Ethers such as propylene glycol phenyl ether; Ketones such as acetophenone; Amides such as
• the liquid pesticide composition may contain one or more surfactants.
• the surfactant include (c1) an ionic surfactant and (c2) a nonionic surfactant.
• examples of the ionic surfactant include anionic surfactants, cationic surfactants and amphoteric surfactants.
• examples of the anionic surfactant include, for example.
• Alkyl sulfonates such as dodecyl sulfonate; Alpha olefin sulfonates such as tetradecene sulfonate; Alkylaryl sulfonates such as alkylbenzene sulfonates and alkylnaphthalene sulfonates; Dialkyl sulfosuccinates such as di (2-ethylhexyl) sulfosuccinate; N-acyl-N-methyl taurine salt such as oleoyl methyl taurine salt; Alkyl sulfate esters such as lauryl sulfate; Polyoxyethylene alkyl ether sulfates such as laureth sulfate; Polyoxyethylene aryl ether sulfate ester salts such as polyoxyethylene distyrylphenyl ether sulfate ester salts; Alkyl phosphate ester salts such as lauryl
• the salts in the sulfonate, the sulfosuccinate, the taurine salt, the sulfate ester salt, the phosphate ester salt, the fatty acid salt, the sarcosine salt, and the glutamate salt are sodium salt, potassium salt, and calcium salt.
• Preferred anionic surfactants include alkyl sulfonates, alkylaryl sulfonates, alkyl sulfates, dialkyl sulfosuccinates and polyoxyethylene aryl ether sulfates. Examples of the cationic surfactant include, for example.
• Alkylamine hydrochlorides such as dodecylamine hydrochloride; Alkyl quaternary ammonium salts such as dodecyltrimethylammonium salt, alkyldimethylbenzylammonium salt, alkylpyridinium salt, alkylisoquinolinium salt and dialkylmorpholinium salt; Benzethonium chloride; Examples thereof include polyvinyl chloride pyridinium salt.
• amphoteric tenside examples include N-laurylalanine, N, N, N-trimethylaminopropionic acid, N, N, N-trihydroxyethylaminopropionic acid, N-hexyl-N, N-dimethylaminoacetic acid, and the like.
• amphoteric tenside examples include 1- (2-carboxyethyl) pyrimidinium betaine and lecithin.
• nonionic surfactants include, for example.
• Polyoxyalkylene block copolymers such as polyoxyethylene polyoxypropylene block copolymers
• Polyoxyalkylene fatty acid esters such as polyoxyethylene fatty acid esters and polyoxyethylene polyoxypropylene fatty acid esters
• Polyoxyalkylene alkyl ethers such as polyoxyethylene alkyl ethers and polyoxyethylene polyoxypropylene alkyl ethers
• Polyoxyalkylene polyaryl ethers such as polyoxyethylene tristyrylphenyl ether, polyoxyethylene polyaryl ether and polyoxyethylene polyoxypropylene polyaryl ether
• Polyoxyalkylene alkylaryl ethers such as polyoxyethylene alkylaryl ethers and polyoxyethylene polyoxypropylene alkylaryl ethers
• Polyoxyalkylene vegetable oils such as polyoxyethylene castor oil and polyoxyethylene polyoxypropylene castor oil
• Polyoxyalkylene hardened vegetable oil such as polyoxyethylene hardened cast
• Preferred nonionic surfactants include polyoxyalkylene block copolymers, polyoxyalkylene alkyl ethers, polyoxyalkylene polyaryl ethers, polyoxyalkylene vegetable oils, copolymers of alkyd resin and polyethylene glycol, sorbitan fatty acid esters, polyoxy. Examples include alkylene sorbitan fatty acid esters.
• liquid pesticide composition may contain other components other than the above, if necessary.
• other components include pesticide active ingredients other than compound (I), pharmaceutical aids, and the like.
• the content of the compound (I) in all the pesticide active ingredients contained in the liquid pesticide composition is, for example, 1% by mass or more and 100. It may be mass% or less, or 3 mass% or more and 100 mass% or less. The content is, for example, 5% by mass or more and 100% by mass or less, 10% by mass or more and 100% by mass or less, 15% by mass or more and 100% by mass or less, 20% by mass or more and 100% by mass or less, or 30% by mass or more and 100% by mass. It is as follows.
• the pesticide active ingredient other than the compound (I) is not particularly limited, and examples thereof include an insecticidal active ingredient, a bactericidal active ingredient, and a herbicidal active ingredient.
• the liquid pesticide composition can contain one or more pesticide active ingredients selected from the group consisting of insecticidal active ingredients, bactericidal active ingredients and herbicidal active ingredients as pesticide active ingredients other than compound (I).
• the insecticidal active ingredient, the bactericidal active ingredient, and the herbicidal active ingredient may contain one kind or two or more kinds of ingredients, respectively.
• herbicidal active ingredient examples include the following. These can also be used in combination with a liquid pesticide composition containing compound (I) as a pesticide active ingredient.
• Herbicides 2,3,6-TBA (2,3,6-trichlorobenzoic acid), 2,3,6-TBA dimethylammonium (2,3,6-TBA-dimethylammonium), 2,3,6-TBA lithium Salt (2,3,6-TBA-lithium), 2,3,6-TBA potassium salt (2,3,6-TBA-potassium), 2,3,6-TBA sodium salt (2,3,6- TBA-sodium), 2,4-D, 2,4-D choline salt, 2,4-D biproamine, 2,4-D doboxyl (2,4-D-doboxyl), 2,4-D 2-ethylhexyl (2,4-D-2-ethylhexyl), 2,4-D 3-butoxypropyl (2,4-
• the herbicidal active ingredients that can be used in combination with the liquid pesticide composition include, in particular, glyphosate potassium salt, glyphosate dimethylamine salt, glyphosate monoethanolamine salt, gluhosinate ammonium salt, gluhosinate P ammonium salt, and glyphosate isopropylammonium salt.
• 2,4-D choline salt 2,4-D dimethylammonium, dicambadiglycolamine salt, dicambaBAPMA salt, dicambatetrabutylamine salt, dicambatetrabutylphosphonium salt, pyroxasulfone, fluminoxazine, flumicrolacpentyl , Cretodium, lactophene, S-metrichlor, metribudin, flufenacet, nicosulfron, limsulfone, acetochlor, mesotrione, isoxaflutol, chlorimlonethyl, thifencelfuronmethyl, chloranthrammethyl, imazetapillammonium Salt is preferred.
• Examples of pharmaceutical aids include antifoaming agents and thickeners.
• Examples of the defoaming agent include silicone-based defoaming agents.
• the content thereof is usually 0.001% by mass or more and 1% by mass or less, preferably 0.% by mass, when the total amount of the liquid pesticide composition is 100% by mass. It is 002% by mass or more and 0.8% by mass or less.
• thickener examples include an organic solvent-soluble or organic solvent-dispersible thickener.
• organic solvent-soluble or organic solvent-dispersible thickener examples include organic clay, organic bentonite, organic montmorillonite, and organically modified castor oil derivative.
• the content thereof is usually 0.01% by mass or more and 20% by mass or less when the total amount of the liquid pesticide composition is 100% by mass.
• liquid pesticide composition (emulsion)
• the liquid pesticide composition can be suitably used as a liquid pesticide preparation called an emulsion (EC) in the field of pesticides.
• EC emulsion
• the total amount of the emulsion is 100% by mass
• the total content of the compound (I), the organic solvent, and the surfactant in the emulsion is preferably 60% by mass or more, more preferably 70% by mass or more. , More preferably 75% by mass or more.
• the total content may be 100% by mass, 95% by mass or less, 90% by mass or less, or 85% by mass or less.
• the content of the organic solvent in the emulsion is preferably 10% by mass or more and 90% by mass or less, more preferably 30% by mass or more and 88% by mass or less, still more preferable. Is 50% by mass or more and 85% by mass or less.
• the content of the organic solvent is usually 3 mass times or more and 50 mass times or less, preferably 4 mass times or more and 40 mass times or less, and more preferably 5 mass times or more and 30 mass times or less the content of the compound (I). It is as follows.
• Adjusting the ratio (mass ratio) of the content of the organic solvent to the content of the compound (I) within the above range is suitable for improving the emulsion stability when the emulsion is mixed with water. be.
• the total content of the ionic surfactant and the nonionic surfactant in the emulsion is preferably 1% by mass or more and 30% by mass or less, more preferably 2% by mass. % Or more and 28% by mass or less, more preferably 4% by mass or more and 26% by mass or less, still more preferably 6% by mass or more and 24% by mass or less, and particularly preferably 8% by mass or more and 22% by mass or less. be.
• the total content of the ionic surfactant and the non-ionic surfactant is preferably 0.1% by mass or more and 30% by mass or less, and more preferably 0.5% by mass or more of the content of the compound (I).
• the emulsion contains one or more nonionic surfactants and one or more ionic surfactants
• the emulsion comprises one or more nonionic surfactants and one or more ionic surfactants.
• the content ratio (mass ratio) is preferably 1: 0.05 to 1:40, more preferably 1: 0.1 to 1:30, and even more preferably 1: 0.2 to 1: 1. 20.
• the liquid pesticide composition which is an emulsion, can be produced by a method generally used as an emulsion production method, and contains, for example, compound (I), an organic solvent, and a surfactant, and components added as necessary. It can be manufactured by mixing.
• Liquid pesticide compositions which are emulsions, are applied to control pests and weeds by the methods commonly used as emulsions. Specifically, the emulsion is mixed with water to prepare an emulsion, and the emulsion is applied to a plant or the soil in which the plant is cultivated.
• the emulsion is usually prepared by mixing with water of 2 to 10000 times, preferably 10 to 8000 times, more preferably 15 to 6000 times the volume of the emulsion.
• an adjuvant may be mixed.
• the type of adjuvant is not particularly limited, but oil-based adjuvants such as Agri-Dex and MSO (mineral oils such as paraffin-based hydrocarbons, naphthen-based hydrocarbons, and aromatic hydrocarbons, or vegetable oils (soybean oil and rapeseed oil)) are used.
• oil-based adjuvants such as Agri-Dex and MSO (mineral oils such as paraffin-based hydrocarbons, naphthen-based hydrocarbons, and aromatic hydrocarbons, or vegetable oils (soybean oil and rapeseed oil)
• esterified Methlated Seed Oil 0.25%, 0.5%, 1%, 2%, 3%, 4%, 5% or 6% (volume / volume), Induce, etc. in the spray liquid, etc.
• nonionic adjuvant polyoxyalkylene alkyl ether, polyoxyalkylene fatty acid ester, alkylaryl alkoxyrate, or alkylaryl polyoxyalkylene glycol
• 0.05%, 0.1%, 0.25 in the spray liquid It is desirable to mix% or 0.5% (volume / volume).
• anionic systems such as Gramin S (substituted sulfonates), cationic systems such as Genamin T 200BM (polyoxyethyleneamine), and organic silicone systems such as Silvert L77.
• drift reducing agent such as Intact (polyethylene glycol) or a volatilization reducing agent such as Vapex, a VaporGrip Xtra Agent (mixture of potassium hydroxide and acetic acid) may be mixed.
• the pH and hardness of the spray liquid are not particularly limited.
• liquid pesticide composition emulsifying agent
• the liquid pesticide composition can be suitably used as a liquid pesticide preparation called an emulsion (EW) in the field of pesticides.
• EW emulsion
• the emulsion contains water. Examples of water include ion-exchanged water, tap water and groundwater. Water constitutes the aqueous phase of the emulsion.
• the content of water in the emulsion is preferably 40% by mass or more and 95% by mass or less, more preferably 50% by mass or more and 93% by mass or less. It is more preferably 60% by mass or more and 90% by mass or less, and further preferably 70% by mass or more and 87% by mass or less. It is preferable that the emulsion contains water in a content within the range from the viewpoint of improving the stability of the emulsion of the liquid pesticide composition.
• the emulsion is an oil droplet emulsion in water containing an aqueous phase and oil phase particles dispersed in the aqueous phase.
• the liquid pesticide composition which is an emulsion can be produced by a general method as a method for producing an emulsion, and for example, compound (I), an organic solvent and a surfactant are mixed to prepare an oil phase. ..
• an aqueous phase is prepared by adding a pesticide active compound other than compound (I), a pharmaceutical additive and water.
• the surfactant may be added to the organic solvent, water, or both.
• the oil phase is added to the aqueous phase, emulsified with a stirrer such as a homogenizer, and mixed with a pharmaceutical auxiliary such as a thickener, a preservative, and an antifoaming agent as necessary to obtain the composition of the present invention.
• a stirrer such as a homogenizer
• a pharmaceutical auxiliary such as a thickener, a preservative, and an antifoaming agent as necessary to obtain the composition of the present invention.
• the liquid pesticide composition which is an emulsion, is applied to control pests and weeds by a method usually used as an emulsion.
• an adjuvant may be mixed when applying the emulsion.
• the state inside the graduated cylinder was visually observed, and the emulsification stability when mixed with water was evaluated according to the following evaluation criteria.
• the evaluation results are shown in Tables 1 and 2. If the evaluation is A or B, it can be said that crystals are difficult to precipitate and grow, and it can be evaluated that the emulsion stability when mixed with water is good.
• C Crystal precipitation is observed.
• Emulsogen TS290 Polyoxyethylene tristyrylphenyl ether, manufactured by Clariant
• Phenylsulfonat CAL mixture of 70% dodecylbenzene sulfonic acid calcium salt and 30% iso-butanol, manufactured by Clariant
• Atlas G5000 polyoxyalkylene block copolymer, manufactured by CRODA
• Atlox 4914 copolymer of alkyd resin and polyethylene glycol, manufactured by CRODA
• 2-Heptanone manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• Benzyl acetate trade name: JEFFSOL AG1705, manufactured by Huntsman
• Butyl propionate manufactured by Wako Pure Chemical Industries, Ltd.
• Methyl benzoate manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.
• Ethyl benzoate manufactured by Wako

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• 2021
  • 2021-11-30 WO PCT/JP2021/043748 patent/WO2022118814A1/ja not_active Ceased
  • 2021-11-30 JP JP2022566916A patent/JP7754845B2/ja active Active
  • 2021-11-30 AU AU2021390291A patent/AU2021390291A1/en active Pending
  • 2021-11-30 CA CA3203620A patent/CA3203620A1/en active Pending
  • 2021-11-30 US US18/254,805 patent/US20230413821A1/en active Pending
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