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WO2011145318A1 - Agent de réduction d'effet néfaste pour un herbicide, composition herbicide ayant un effet néfaste réduit, et procédé pour la réduction de l'effet néfaste sur les cultures - Google Patents

Agent de réduction d'effet néfaste pour un herbicide, composition herbicide ayant un effet néfaste réduit, et procédé pour la réduction de l'effet néfaste sur les cultures Download PDF

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Publication number
WO2011145318A1
WO2011145318A1 PCT/JP2011/002699 JP2011002699W WO2011145318A1 WO 2011145318 A1 WO2011145318 A1 WO 2011145318A1 JP 2011002699 W JP2011002699 W JP 2011002699W WO 2011145318 A1 WO2011145318 A1 WO 2011145318A1
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compounds
herbicide
compound
group
hydrogen atom
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PCT/JP2011/002699
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English (en)
Japanese (ja)
Inventor
平岡学
高橋優樹
高橋亨
池内利祐
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Kumiai Chemical Industry Co Ltd
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Kumiai Chemical Industry Co Ltd
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Priority to JP2012515745A priority Critical patent/JP5814232B2/ja
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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
    • 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
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
    • 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
    • A01N37/00—Biocides, 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • 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
    • A01N37/00—Biocides, 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
    • A01N37/36—Biocides, 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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, 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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A01N37/40—Biocides, 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 at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/86—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • 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
    • A01N47/00—Biocides, 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
    • A01N47/08—Biocides, 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a herbicide safener that can reduce or prevent phytotoxicity and reduce the environmental load without using multiple different herbicidal active ingredients in combination, herbicide composition with reduced phytotoxicity, and crop phytotoxicity. Relates to a method of reducing
  • pyrimisulphan has a high herbicidal effect on low-dose annual perennial weeds such as Novier, Tamagayatsuri, Konagi and Himehoshihagi, and perennial weeds such as pine bay, Urikawa and Omodaka, especially paddy weeds. It is known as having a broad herbicidal spectrum (see Patent Document 1).
  • Patent Literature a combination of pyrimisulphan and other specific herbicidal active compounds such as pretilachlor and butachlor (Patent Literature). 3)), however, a technology that achieves both a high herbicidal effect and safety for rice without using a plurality of herbicidal active compounds has not yet been established.
  • JP 2000-44546 A (Claims and others) European Patent EP-A122231 (Claims and others) JP 2000-281513 (Claims and others)
  • the problem of the present invention is that, under such circumstances, when the herbicidal active ingredient is simply applied, the growth of the target crops such as rice, growth inhibition, growth inhibition, phytotoxicity such as lateralization, etc. are manifested. Even if it is such, the phytotoxicity mitigation agent for herbicides that can reduce or prevent the phytotoxicity symptoms of the target crop without using multiple herbicidal active ingredients of different types and without sacrificing the herbicidal effect
  • An object of the present invention is to provide a herbicidal composition with reduced phytotoxicity and a method for reducing phytotoxicity of crops.
  • sulfonylurea compounds, sulfonamide compounds, chloroacetanilide compounds which are known herbicidal active compounds, Thiocarbamate compounds, pyrimidinyloxy (thio) benzoic acid compounds, tetrazolinone compounds, triazole compounds, pyrazole compounds, cyclohexanedione compounds, phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds, and It has been found that a herbicidal composition comprising a specific compound that does not exhibit exceptional agrochemical activity per se in an isoxazoline-based compound or a salt thereof contributes to solving the problems, and the present invention is made based on this finding. It came.
  • the present invention provides a phytotoxicity reducing agent for herbicides as described below, a herbicide composition with reduced phytotoxicity, and a method for reducing phytotoxicity, particularly for grasses, using the herbicide.
  • R 1 is a hydrogen atom
  • R 2 and R 3 are C4 to C5 alkyl groups
  • X is an amino group or a hydroxymethyl group
  • Y is a hydrogen atom.
  • herbicidal active compounds selected from phenoxycarboxylic acid compounds, oxazinone compounds, difluoromethanesulfonylanilide compounds and isoxazoline compounds, or salts thereof, A herbicidal composition with reduced phytotoxicity.
  • the herbicide reducing agent and herbicide composition with reduced phytotoxicity of the present invention includes a wide range of herbicidally active compounds, and when applied simply, it prevents growth disturbance, growth inhibition, and division inhibition of target crops such as rice. Even if it causes phytotoxicity symptoms such as yellowing, the phytotoxicity symptoms of the target crop can be reduced or prevented without sacrificing sufficient herbicidal effect. It is useful as a phytotoxicity reducing agent for herbicides or a herbicidal composition with reduced phytotoxicity, particularly as a phytotoxicity reducing agent or agrochemical composition for rice action or rice field rice action.
  • the method of the present invention can be applied to the target crop, particularly rice, even if the herbicidal active compound is applied so that phytotoxic symptoms such as growth inhibition, growth inhibition, and yellowing occur. Since it can reduce or prevent phytotoxic symptoms, it is useful as a method for reducing phytotoxicity of crops by herbicidal active compounds.
  • R 1 represents a hydrogen atom, a hydroxyl group or a C4 to C5 alkyl group
  • R 2 represents a hydrogen atom.
  • R 3 represents a C4 to C5 alkyl group
  • X represents a carboxyl group, an amino group, a hydroxyl group or a hydroxymethyl group
  • Y represents a hydrogen atom or a hydroxyl group.
  • R 1 and R 2 is a C4 to C5 alkyl group.
  • R 1 is a hydrogen atom or a hydroxyl group
  • R 2 and R 3 are C4 to C5 alkyl groups
  • Y is a hydrogen atom or a hydroxyl group
  • R 1 is a hydrogen atom
  • R 2 and R 3 are C4 to C5 alkyl groups
  • X is a carboxyl group
  • Y is a hydrogen atom or a hydroxyl group
  • R 1 is a hydrogen atom
  • R 2 and R 3 are C4-C5 alkyl groups
  • X is an amino group or a hydroxymethyl group
  • Y is a hydrogen atom.
  • Mention may be made of 3,5-di-tert-butylaniline and 3,5-di-tert-butylbenzyl alcohol.
  • R 1 is a hydroxyl group
  • R 2 and R 3 are C4 to C5 alkyl groups
  • X is a hydroxyl group
  • Y is a hydrogen atom
  • R 1 and R 3 are C4 to C5 alkyl groups
  • R 2 is a hydrogen atom
  • X and Y are hydroxyl groups
  • 2,5-di-tert-butylhydroquinone and 2,5-di- (1,1-dimethylpropyl) hydroquinone can be mentioned.
  • the C4-C5 alkyl group is preferably a tert-butyl group or a 1,1-dimethylpropyl group containing a quaternary carbon.
  • the safener for a herbicide of the present invention may be a compound represented by one or more general formulas (I) per se or a pesticide carrier described later.
  • herbicidal composition with reduced phytotoxicity of the present invention (A) Component: A herbicide safener (B) component comprising as a main component the compound represented by the above general formula (I) component: 1 or 2 or more specific herbicidal active compounds are contained. Is.
  • herbicidal active compounds of the component (B) used in combination with the component (A) include, for example, clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, diclohop-P.
  • naproanilide naproanilide, acetochlor, alachlor, butachlor, butenachlor, diethyl-ethyl, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor, dimethachlor. dimethachlor.
  • Metazachlor metolachlor, metolachlor, petoxamide, pretilachlor, propachlor, propisochlor, or S-metolachlor Nylchlor, flufenacet, mefenacet, fentrazamide, fenoxasulfone, pyroxasulone, isoxaben, isoxaben, isoxaben , Flupoxam, dinoterb, DNOC (including salts such as amines or sodium), benfrateate, etofumesate, dalapon, flupropanate, CA Including salts such as thorium, calcium or ammonia), benzulide, butyrate, cycloate, dimpiperate, EPTC, esprocarb, molinate, orbencarb (Pebulate), prosulfocarb, thiobencarb, thiocarbazil, tri-allate, vernarate, chlor
  • sulfonylurea compounds such as bensulfuron methyl, pyrazosulfuron ethyl, halosulfuron methyl, azimusulfuron, synosulfuron, cyclosulfamuron, flucetosulfuron, imazosulfuron, ethoxysulfuron, or propyrisulfuron;
  • sulfonamide compounds such as penox slam; Chloroacetanilide compounds such as butachlor, pretilachlor or tenyl chlor;
  • thiocarbamate compounds such as thiobencarb, esprocarb or molinate;
  • pyrimidinyloxy (thio) benzoic acid compounds such as pyriminobacmethyl, pyriftalide, bispyribac sodium or pyribenzoxime;
  • tetrazolinone compounds such as bensulfuron methyl, pyrazosulfuron ethyl, halos
  • component (B) used in the herbicidal composition of the present invention is, for example, published by The Pesticide Manual 14th edition [British Crop Protection Council]. 2006], WO94 / 008999, WO00 / 021924, and WO03 / 061388.
  • Phenoxasulfone that is, 3- (2,5-dichloro-4-ethoxybenzylsulfonyl) -4,5-dehydro-5,5-dimethoxyisoxazole is described in WO01 / 012613.
  • examples of the salt include a salt of an alkali metal such as sodium or potassium; a salt of an alkaline earth metal such as calcium, magnesium or barium; a salt of a transition metal such as manganese, copper, zinc or iron; an ammonium salt; Salts with inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid; C1-C4 alkyl sulfonic acids such as methane sulfonic acid, aromatic sulfonic acids such as benzene sulfonic acid or toluene sulfonic acid, oxalic acid, maleic acid And salts with organic acids such as fumaric acid, lactic acid, tartaric acid, adipic acid or benzoic acid.
  • inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid or sulfuric acid
  • C1-C4 alkyl sulfonic acids such as methane sulfonic acid, aromatic sul
  • a herbicidally active compound other than the above may be used in combination.
  • the use ratio of the component (A) and the component (B) can be appropriately changed depending on the type of both, the type and growth period of the target crop, for example, the transplanting period in rice and the like.
  • the mass of the component (A) is usually 0.1 to 200 times the mass of the component (B).
  • the application amount of the component (A) is not particularly limited, but is usually 10 to 5000 g, preferably 50 to 3000 g, more preferably 100 to 2000 g per hectare of farmland. Is selected within the range.
  • the application amount of the component (B) is not particularly limited, but usually per hectare of farmland,
  • For sulfonylurea compounds 1 to 200 g, preferably 5 to 100 g,
  • For sulfonamide compounds 5 to 50 g, preferably 10 to 30 g
  • In the case of chloroacetanilide compounds 50 to 3000 g, preferably 100 to 2000 g
  • For thiocarbamate compounds 500 to 5000 g, preferably 1000 to 4000 g
  • For pyrimidinyloxy (thio) benzoic acid compounds 5 to 500 g, preferably 10 to 200 g
  • For tetrazolinone compounds 50 to 1000 g, preferably 100 to 500 g
  • For triazole compounds 50 to 1000 g, preferably 100 to 500 g,
  • For pyrazole compounds 100 to 5000 g, preferably 500 to 3000 g
  • For cyclohexanedione compounds 5 to 1000 g
  • the herbicidal composition of the present invention can contain additive components usually used in agricultural chemical formulations as necessary.
  • a carrier such as a solid carrier or a liquid carrier, a surfactant, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, an antifreezing agent, an anti-caking agent, Examples include disintegrants and decomposition inhibitors.
  • These additive components may be used alone or in combination of two or more.
  • solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth; inorganic such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride Salts: Organic solid carriers such as synthetic silicic acid, synthetic silicates, starches, celluloses, plant powders; plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, and the like.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Such alcohols polyhydric alcohol compounds such as propylene glycol ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone; ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, Ethers such as tetrahydrofuran; aliphatic hydrocarbons such as normal paraffin, naphthene, isoparaffin, kerosene, mineral oil Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha and alkylnaphthalene; halogenated hydrocarbons such as dichloroethane, chloroform and carbon tetrachloride; ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, adipic acid
  • surfactant examples include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene alkyl ether, polyoxyethylene Ethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxyethylene polypropylene block polymer ether, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid Bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkyl Nonionic surfactants such as styrylphenyl ether, acetylene diol, polyoxyalkylene-added acetylene diol, polyoxyethylene ether type silicone, ester type silicone, fluorine surfact
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6000.
  • examples include polyethylene glycol having a molecular weight of ⁇ 20,000, polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, and phospholipids (for example, cephalin and lecithin).
  • thickener examples include water-soluble polymers such as xanthan gum, guar gum, welan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound and water-soluble polysaccharide; high-purity bentonite, fumed silica Inorganic fine powder such as (fumed silica, white carbon).
  • water-soluble polymers such as xanthan gum, guar gum, welan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compound and water-soluble polysaccharide
  • high-purity bentonite fumed silica Inorganic fine powder such as (fumed silica, white carbon).
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue; organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
  • the spreading agent examples include silicone surfactant, cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinyl pyrrolidone, maleic acid and styrene copolymer, (meth) acrylic acid copolymer And a half ester of a polymer composed of a polyhydric alcohol and a dicarboxylic anhydride, a water-soluble salt of polystyrene sulfonic acid, and the like.
  • the spreading agent examples include paraffin, terpene, polyamide resin, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • anti-caking agent examples include polysaccharides such as starch, alginic acid, mannose, and galactose, polyvinylpyrrolidone, fumed silica (fumed silica, white carbon), ester gum, and petroleum resin.
  • disintegrating agents include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride
  • disintegrating agents include sodium tripolyphosphate, sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride
  • examples include acid copolymers and starch / polyacrylonitrile graft copolymers.
  • decomposition inhibitor examples include desiccants such as zeolite, quicklime, and magnesium oxide, and UV absorbers such as salicylic acid and benzophenone.
  • preservative examples include potassium sorbate, 1,2-benzthiazolin-3-one and the like.
  • plant pieces examples include sawdust, coconut husk, corn cob, and tobacco stem.
  • the content is usually 5 to 95% for the carrier, preferably 20 to 90%, and usually 0.1% to about 10% for the surfactant. It is selected in the range of 30%, preferably 0.5 to 10%, and other additives in the range of 0.1 to 30%, preferably 0.5 to 10%.
  • the herbicidal composition of the present invention may be any solution, emulsion, wettable powder, powder, oil, granular wettable powder, flowable powder, milk suspension, granule, jumbo drug, suspoemulsion, microcapsule, etc. It is used by formulating into a dosage form.
  • a mixed composition with agrochemicals other than the component (B) for example, other herbicides, insecticides, fungicides, plant growth regulators, fertilizers and the like can also be obtained.
  • the herbicidal composition of the present invention may be in a form in which the above-mentioned arbitrary preparation is packaged with a water-soluble film, and when applied in this form, it can contribute to labor saving and increase safety.
  • the herbicidal composition of the present invention can be applied at any time from the occurrence of weeds to the growing season to express both weed control and reduction of phytotoxicity to the target crop. Is preferred because the application effect of the herbicidal composition of the present invention is most remarkable.
  • the component (A) and the component (B) may be applied simultaneously or in close proximity.
  • the proximity application means that the component (A) is applied while the period from the application of the component (B) is approached before the phytotoxicity of the target crop due to the component (B) is not manifested.
  • it can be applied in the form of a ready mix.
  • the pre-formulated composition of the present invention may be used, or the component (A) and the component (B) may be used separately. And can be applied in the form of an in-situ formulation that is mixed at the time of use, ie in the form of a tank mix.
  • the manufacturing method in particular of the herbicidal composition of this invention is not restrict
  • (1) A method of adding an appropriate amount of water to a mixture of all raw materials, kneading, extruding from a screen with a hole of a certain size, granulating and drying.
  • (2) A method in which a safener, a herbicidal active compound and a surfactant are dissolved or suspended in an organic solvent and adsorbed on a carrier.
  • Examples 1 to 16 Hydroponic test Murashige / Skoog medium salt made by Wako Pure Chemical Industries, Ltd. 25% aqueous solution of various safeners, that is, (A) component is added to a concentration of 10ppm, and a predetermined amount of weeding
  • the active ingredient, ie component (B) was added. 50 mL of this solution was dispensed into an Erlenmeyer flask to prepare various liquid media.
  • a liquid medium hereinafter referred to as “untreated medium” containing 50 mL of a 25% salt aqueous solution for Murashige-Skoog medium was prepared.
  • Comparative Examples 1-5 (A) The rice which cut
  • disconnected the root part to the length of 1 cm beforehand was grown by the liquid culture medium prepared like the Example except not having added the component, and the length of the root part was measured 7 days afterward. The average value (n 3) of the measured values was taken, and the percentage (non-treated group ratio) with respect to the average value of the measured values of the untreated group was determined. The results are shown in Tables 1 and 2.
  • the “untreated section” means a crop classification in which the crop is grown on the untreated medium.
  • Example 17 Add appropriate amount of water to 2 parts of 3,5-di-tert-butylcatechol, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 69 parts of calcium carbonate. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylcatechol and phenoxasulfone were obtained.
  • Example 18 Add an appropriate amount of water to 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 66 parts of calcium carbonate. After kneading, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzoic acid and phenoxasulfone were obtained.
  • Example 19 Appropriate amounts of 10 parts 3,5-di-tert-butyl-4-hydroxybenzoic acid, 2 parts phenoxasulfone, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 61 parts calcium carbonate
  • extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator.
  • a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butyl-4-hydroxybenzoic acid and phenoxasulfone were obtained.
  • Example 20 Add 10 parts of 3,5-di-tert-butylaniline, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 61 parts of calcium carbonate and knead with appropriate amount of water. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylaniline and phenoxasulfone were obtained.
  • Example 21 Add appropriate amount of water to 10 parts of 3,5-di-tert-butylbenzyl alcohol, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 61 parts of calcium carbonate. After kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzyl alcohol and phenoxasulfone were obtained.
  • Example 22 Add appropriate amount of water to 20 parts of 2,5-di-tert-butylhydroquinone, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 51 parts of calcium carbonate. Then, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. The granules containing 2,5-di-tert-butylhydroquinone and phenoxasulfone were obtained by drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving.
  • Example 23 Impact grinding of 10 parts of 2,5-di- (1,1-dimethylpropyl) hydroquinone, 10 parts of phenoxasulfone, 5 parts of fumed silica (white carbon), 10 parts of sodium salt of alkylnaphthalene sulfonate and 65 parts of clay A wettable powder containing 2,5-di- (1,1-dimethylpropyl) hydroquinone and phenoxasulfone was obtained by mixing and grinding using a machine.
  • Example 24 Wet 2 parts 3,5-di-tert-butylbenzoic acid, 4 parts phenoxasulfone, 5 parts polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts propylene glycol, 0.3 part xanthan gum and 78.7 parts water
  • a flowable agent containing 3,5-di-tert-butylbenzoic acid and phenoxasulfone was obtained by mixing and pulverizing glass beads as a pulverizing medium using a pulverizer.
  • Example 25 Appropriate amount for 8 parts of 3,5-di-tert-butylbenzoic acid, 8 parts of phenoxasulfone, 3 parts of enzyme-modified dextrin, 3 parts of acetylenic diol, 12 parts of water-containing plastic hollow beads, 20 parts of anhydrous sodium sulfate and 46 parts of urea After adding water and kneading, extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator.
  • Example 26 To 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of phenoxasulfone, 1 part of bensulfuron methyl, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 65 parts of calcium carbonate After an appropriate amount of water was added and kneaded, extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzoic acid, phenoxasulfone and bensulfuron methyl were obtained.
  • Example 27 Extruded granulation after kneading an appropriate amount of water into 10 parts of 3,5-di-tert-butylcatechol, 1 part of pyrimisulphan, 3 parts of pregelatinized starch, 1 part of sodium dodecylbenzenesulfonate and 85 parts of clay Extrusion granulation was carried out from a screen having an opening diameter of 1 mm using a machine. Granules containing 3,5-di-tert-butylcatechol and pyrimylsulfan were obtained by drying with a fluid bed dryer at a product temperature of 60 ° C. and sieving.
  • Example 28 Wet 5 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of pyrimylsulfan, 5 parts of polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and 77.7 parts of water A flowable agent containing 3,5-di-tert-butylbenzoic acid and pyrimisulfurphan was obtained by mixing and pulverizing glass beads using a pulverizer as a pulverizing medium.
  • Example 29 Appropriate amount of water in 2 parts of 3,5-di-tert-butylcatechol, 3 parts of pyrimyl fan, 3 parts of enzyme-modified dextrin, 3 parts of acetylenic diol, 12 parts of water-containing plastic hollow beads, 20 parts of anhydrous sodium sulfate and 57 parts of urea After kneading and extruding, extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator.
  • Floating diffusion type granules containing 3,5-di-tert-butylcatechol and pyrimylsulfane by sizing to a length of 3-20 mm, drying in a fluid bed dryer at a product temperature of 60 ° C., and sieving. An agent was obtained.
  • Example 30 Add appropriate amount of water to 10 parts 3,5-di-tert-butylbenzyl alcohol, 1 part pyriminobac-methyl, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 62 parts calcium carbonate. After kneading, the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator. By drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylbenzyl alcohol and pyriminobac-methyl were obtained.
  • Example 31 3,5-di-tert-butylbenzoic acid 10 parts, pyriminobacmethyl 2 parts, bensulfuron methyl 3 parts, enzyme-modified dextrin 3 parts, acetylene diol 3 parts, hydrous plastic hollow beads 12 parts, anhydrous sodium sulfate 20 parts
  • extrusion granulation was performed from a screen having an opening diameter of 5 mm using an extrusion granulator. After sizing to a length of 3 to 20 mm, drying in a fluidized bed dryer at a product temperature of 60 ° C. and sieving, 3,5-di-tert-butylbenzoic acid, pyriminobacmethyl and bensulfuronmethyl are obtained. The contained floating diffusion type granule was obtained.
  • Example 32 3,5-di-tert-butylbenzyl alcohol 5 parts, thiobencarb 5 parts, enzyme-modified dextrin 1 part, dioctyl sulfosuccinate sodium salt 1 part, fumed silica (white carbon) 5 parts, diatomaceous earth 10 parts, bentonite 25 parts
  • the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator.
  • the granules containing 3,5-di-tert-butylbenzyl alcohol and thiobencarb were obtained by drying with a fluid bed dryer at a product temperature of 50 ° C. and sieving.
  • Example 33 After kneading an appropriate amount of water in 10 parts of 2,5-di-tert-butylhydroquinone, 3 parts of fentolazamide, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 60 parts of calcium carbonate Extrusion granulation was performed from a screen having an aperture diameter of 1 mm using an extrusion granulator. The granules containing 2,5-di-tert-butylhydroquinone and fentolazamide were obtained by drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving.
  • Example 34 Wet pulverize 10 parts of 3,5-di-tert-butylhydroquinone, 1 part of oxadichromephone, 5 parts of polyoxyethylene styryl phenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and 73.7 parts of water.
  • the flowable agent containing 3,5-di-tert-butylhydroquinone and oxadichromemephone was obtained by mixing and grinding the glass beads as a grinding medium.
  • Example 35 35 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of caffeentrol, 4 parts of benzobicyclone, 5 parts of polyoxyethylene styrylphenyl ether sulfate sodium salt, 10 parts of propylene glycol, 0.3 part of xanthan gum and water Seven parts were mixed and pulverized using glass beads as a pulverization medium using a wet pulverizer to obtain a flowable agent containing 3,5-di-tert-butylbenzoic acid, caffeentrol and benzobicyclone.
  • Example 36 3,5-di-tert-butylbenzyl alcohol 5 parts, butachlor 5 parts, enzyme-modified dextrin 1 part, dioctyl sulfosuccinate sodium salt 1 part, fumed silica (white carbon) 5 parts, diatomaceous earth 10 parts, bentonite 25 parts
  • the mixture was extruded and granulated from a screen having an opening diameter of 1 mm using an extrusion granulator.
  • Granules containing 3,5-di-tert-butylbenzyl alcohol and butachlor were obtained by drying with a fluid bed dryer at a product temperature of 50 ° C. and sieving.
  • Example 37 After kneading with 20 parts of 3,5-di-tert-butylcatechol, 1 part of penox slam, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 52 parts of calcium carbonate with an appropriate amount of water. Extrusion granulation was performed from a screen having an aperture diameter of 1 mm using an extrusion granulator. By drying with a fluid bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butylcatechol and penox slam were obtained.
  • Example 38 2,5-di- (1,1-dimethylpropyl) hydroquinone 3 parts, oxadichromemephone 1 part, chromeprop 3 parts, polyoxyethylene styrylphenyl ether sulfate sodium salt 5 parts, propylene glycol 10 parts, xanthan gum 0.3 part and water
  • a flowable agent containing 2,5-di- (1,1-dimethylpropyl) hydroquinone, oxadichromemephone and chromeprop was prepared by mixing and grinding 77.7 parts with a glass bead as a grinding medium using a wet grinding machine. Obtained.
  • Example 39 Appropriate amount of 4 parts 3,5-di-tert-butyl-4-hydroxybenzoic acid, 8 parts benzofenap, 1 part enzyme-modified dextrin, 1 part dioctylsulfosuccinate sodium salt, 25 parts bentonite and 61 parts calcium carbonate
  • extrusion granulation was performed from a screen having an opening diameter of 1 mm using an extrusion granulator.
  • a fluidized bed dryer at a product temperature of 70 ° C. and sieving, granules containing 3,5-di-tert-butyl-4-hydroxybenzoic acid and benzophenap were obtained.
  • Example 40 By mixing and grinding 10 parts of 3,5-di-tert-butylbenzoic acid, 2 parts of alkylnaphthalenesulfonic acid sodium salt, 30 parts of diatomaceous earth and 58 parts of clay using an impact pulverizer, 3,5-di- A wettable powder containing tert-butylbenzoic acid was obtained. Separately, 2 parts of phenoxasulfone, 1 part of enzyme-modified dextrin, 1 part of dioctylsulfosuccinate sodium salt, 25 parts of bentonite and 71 parts of calcium carbonate were kneaded with an appropriate amount of water, and then examined using an extrusion granulator.
  • the granules containing phenoxasulfone were obtained by drying with a fluidized bed dryer at a product temperature of 70 ° C. and sieving. This wettable powder and granule were simultaneously applied to paddy weeds.
  • Example 41 The granule containing phenoxasulfone produced in Example 40 was applied to paddy weeds, and after 3 days, the wettable powder containing 3,5-di-tert-butylbenzoic acid produced in Example 40 was added. Applied to paddy weeds.
  • Example 42 The wettable powder containing 3,5-di-tert-butylbenzoic acid produced in Example 40 was applied to paddy weeds, and after 7 days, the granule containing phenoxasulfone produced in Example 40 was used. Applied to paddy weeds.

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Abstract

La présente invention concerne : un agent de réduction d'effet néfaste pour un herbicide, qui peut réduire ou supprimer un effet néfaste et peut réduire une charge environnementale sans nécessiter l'utilisation de différents types multiples de composants actifs sur le plan herbicide en combinaison ; une composition herbicide ayant un effet néfaste réduit ; et un procédé pour réduire un effet néfaste sur les cultures. L'agent de réduction d'effet néfaste pour un herbicide est caractérisé en ce qu'il contient, en tant que composant principal, un composé représenté par la formule générale (I) (dans laquelle R1 représente un atome d'hydrogène, un groupe hydroxyle ou un groupe alkyle en C4-C5 ; R2 représente un atome d'hydrogène ou un groupe alkyle en C4-C5 ; R3 représente un groupe alkyle en C4-C5 ; X représente un groupe carboxyle, un groupe amino, un groupe hydroxyle ou un groupe hydroxyméthyle ; et Y représente un atome d'hydrogène ou un groupe hydroxyle, où l'un de R1 et R2 représente un groupe alkyle en C4-C5). La composition herbicide ayant un effet néfaste réduit est caractérisée en ce qu'elle contient l'agent de réduction d'effet néfaste pour un herbicide et au moins un composé actif sur le plan herbicide spécifique.
PCT/JP2011/002699 2010-05-18 2011-05-16 Agent de réduction d'effet néfaste pour un herbicide, composition herbicide ayant un effet néfaste réduit, et procédé pour la réduction de l'effet néfaste sur les cultures Ceased WO2011145318A1 (fr)

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Cited By (5)

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JP2012167080A (ja) * 2011-01-26 2012-09-06 Nissan Chem Ind Ltd 安定化される農薬固型製剤
JP2015110542A (ja) * 2013-03-29 2015-06-18 日産化学工業株式会社 除草剤用薬害軽減剤及び薬害が軽減された除草剤組成物
WO2016115883A1 (fr) * 2015-01-19 2016-07-28 Jiangsu Rotam Chemistry Co., Ltd. Composition herbicide et procédé de lutte contre la croissance de plantes
CN107207415A (zh) * 2015-01-19 2017-09-26 Upl 有限公司 敌稗的结晶变型
JP2019019062A (ja) * 2017-07-13 2019-02-07 クミアイ化学工業株式会社 農薬活性成分の溶出が制御された農薬組成物

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JP2013209365A (ja) * 2012-02-27 2013-10-10 Sumitomo Chemical Co Ltd 農薬製剤

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US4117010A (en) * 1976-09-08 1978-09-26 Stauffer Chemical Company Thiolcarbamate sulfoxides stabilized with hindered phenols
WO2006016527A1 (fr) * 2004-08-11 2006-02-16 Kumiai Chemical Industry Co., Ltd. Composition chimique pour l’agriculture
JP2007501197A (ja) * 2003-08-05 2007-01-25 バイエル クロップサイエンス ゲーエムベーハー 薬害軽減剤としての芳香族化合物の使用
JP2010163420A (ja) * 2008-08-29 2010-07-29 Zenkoku Nogyo Kyodo Kumiai Rengokai 除草剤組成物

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US4117010A (en) * 1976-09-08 1978-09-26 Stauffer Chemical Company Thiolcarbamate sulfoxides stabilized with hindered phenols
JP2007501197A (ja) * 2003-08-05 2007-01-25 バイエル クロップサイエンス ゲーエムベーハー 薬害軽減剤としての芳香族化合物の使用
WO2006016527A1 (fr) * 2004-08-11 2006-02-16 Kumiai Chemical Industry Co., Ltd. Composition chimique pour l’agriculture
JP2010163420A (ja) * 2008-08-29 2010-07-29 Zenkoku Nogyo Kyodo Kumiai Rengokai 除草剤組成物

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012167080A (ja) * 2011-01-26 2012-09-06 Nissan Chem Ind Ltd 安定化される農薬固型製剤
JP2015110542A (ja) * 2013-03-29 2015-06-18 日産化学工業株式会社 除草剤用薬害軽減剤及び薬害が軽減された除草剤組成物
WO2016115883A1 (fr) * 2015-01-19 2016-07-28 Jiangsu Rotam Chemistry Co., Ltd. Composition herbicide et procédé de lutte contre la croissance de plantes
CN107207415A (zh) * 2015-01-19 2017-09-26 Upl 有限公司 敌稗的结晶变型
JP2018502923A (ja) * 2015-01-19 2018-02-01 ユーピーエル リミテッドＵｐｌ Ｌｉｍｉｔｅｄ 結晶性改質プロパニル
JP2019019062A (ja) * 2017-07-13 2019-02-07 クミアイ化学工業株式会社 農薬活性成分の溶出が制御された農薬組成物

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