WO2019124565A1 - Composé nitrophénol, et composition de fongicide synergique comprenant un composé à activité fongicide - Google Patents

Composé nitrophénol, et composition de fongicide synergique comprenant un composé à activité fongicide Download PDF

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Publication number
WO2019124565A1
WO2019124565A1 PCT/JP2018/047403 JP2018047403W WO2019124565A1 WO 2019124565 A1 WO2019124565 A1 WO 2019124565A1 JP 2018047403 W JP2018047403 W JP 2018047403W WO 2019124565 A1 WO2019124565 A1 WO 2019124565A1
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Prior art keywords
compound
inhibitor
group
nitrophenol
bactericidal
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PCT/JP2018/047403
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English (en)
Japanese (ja)
Inventor
悟 常岡
義紀 山本
直孝 林
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Ｏａｔアグリオ株式会社
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Application filed by Ｏａｔアグリオ株式会社 filed Critical Ｏａｔアグリオ株式会社
Priority to KR1020207021579A priority Critical patent/KR20200104359A/ko
Priority to JP2019560607A priority patent/JP7029186B2/ja
Publication of WO2019124565A1 publication Critical patent/WO2019124565A1/fr

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    • 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
    • A01N37/52—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 groups, e.g. carboxylic acid amidines
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
    • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
    • A01N33/22—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
    • A—HUMAN NECESSITIES
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    • A01N37/34—Nitriles
    • A—HUMAN NECESSITIES
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    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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Definitions

  • the present invention relates to a synergistic germicidal composition
  • a synergistic germicidal composition comprising a nitrophenol compound and a germicidally active compound.
  • bactericidal composition in which the bactericidal activity is improved by a synergistic effect by combining two or more existing bactericidally active compounds (Patent Document 1).
  • nitrophenol compounds are disclosed to have a plant growth promoting effect (Patent Document 2) and a BT toxin (insecticidal protein) production promoting effect (Patent Document 3), but nitrophenol is a bactericidal agent. There is no description or suggestion that it is an activity enhancer.
  • An object of the present invention is to provide a synergistic bactericidal composition having an even better control effect against agricultural and horticultural pathogens.
  • the present invention relates to a synergistic germicidal composition and the like comprising the following nitrophenol compound and a germicidally active compound.
  • a synergistic germicidal composition comprising (A) a nitrophenol compound and (B) a germicidally active compound.
  • Item 2. (B) a bactericidal compound is (B1) RNA polymerase inhibitor (A1), (B2) ⁇ -tubulin polymerization inhibitor (B1, 2, 3), (B3) Delocalizer for spectrin-like protein (B5), (B4) respiratory chain complex II (succinic acid dehydrogenase) inhibitor (C2), (B5) Respiratory chain complex III (ubiquinol oxidase, Qo site) inhibitor (C3), (B6) respiratory chain complex III (ubiquinone reductase, Qi site) inhibitor (C4), (B7) uncoupling agent (C5) in oxidative phosphorylation (B8) respiratory chain complex III (ubiquinone reductase, Qo site) inhibitor (C8), (B9) a methyltransferase inhibitor of phospholipid biosynthesis (F2), (B10) Cell membrane
  • a bactericidal compound is (B1) RNA polymerase inhibitor (A1), (B2) ⁇ -tubulin polymerization inhibitor (B3), (B3) Delocalizer for spectrin-like protein (B5), (B4) respiratory chain complex II (succinic acid dehydrogenase) inhibitor (C2), (B5) Respiratory chain complex III (ubiquinol oxidase, Qo site) inhibitor (C3), (B6) respiratory chain complex III (ubiquinone reductase, Qi site) inhibitor (C4), (B7) uncoupling agent (C5) in oxidative phosphorylation (B8) respiratory chain complex III (ubiquinone reductase, Qo site) inhibitor (C8), (B9) a methyltransferase inhibitor of phospholipid biosynthesis (F2), (B10) Cell membrane permeable fatty acid (F4), (B9) a methyltransferase inhibitor of phospholipid biosynthesis (F2), (B10) Cell membrane permeable fatty acid
  • a bactericidal compound is (B1) RNA polymerase inhibitor (A1), (B2) ⁇ -tubulin polymerization inhibitor (B3), (B3) Delocalizer for spectrin-like protein (B5), (B4) respiratory chain complex II (succinic acid dehydrogenase) inhibitor (C2), (B5) Respiratory chain complex III (ubiquinol oxidase, Qo site) inhibitor (C3), (B6) respiratory chain complex III (ubiquinone reductase, Qi site) inhibitor (C4), (B7) uncoupling agent (C5) in oxidative phosphorylation (B8) respiratory chain complex III (ubiquinone reductase, Qo site) inhibitor (C8), (B10) Cell membrane permeable fatty acid (F4), (B11) lipid homeostasis, metastasis, storage inhibitor (F9), (
  • RNA polymerase inhibitor (A1) is an acyl alanine compound
  • B2) ⁇ -tubulin polymerization inhibitor (B3) is an ethylaminothiazole carboxamide compound
  • B3 The delocalizing agent for spectrin-like protein (B5) is a pyridinyl methyl benzamide compound
  • B4 a respiratory chain complex II (succinic acid dehydrogenase) inhibitor
  • C2 is a pyridine carboxamide compound
  • Respiratory chain complex III (ubiquinol oxidase, Qo site) inhibitor (C3) is a methoxycarbamate compound, a methoxyacrylate compound, and an oximinoacetic acid compound, an oxazolidinedione compound
  • B6 Respiratory chain complex III (ubiquinone reductase, Qi site) inhibitor (C4) is a cyanoimidazole compound
  • B7 The uncoupling agent (C5) in oxidative
  • the bactericidally active compounds are metalaxyl, metalaxyl M, boscalid, pyraclostrobin, azoxystrobin, trifloxystrobin, clesoxim methyl, picoxystrobin, cyazofamid, famoxadone, ametocutrazine, fluazinam, tetraconazole, oxys Poconazole fumarate, flutriaphor, chlorothalonil, manzeb, dimethomorph, mandipropamide, etaboxam, acibenzolar-S-methyl, fluopicolide, propamocarb hydrochloride, fosetyl aluminum, phosphorous acid or salts thereof, oxathiapiproline, nonylphenol sulfonic acid
  • Item 7. The synergistic germicidal composition according to any one of Items 1 to 6, wherein the (A) nitrophenol compound is a phenol compound having one nitro group.
  • Item 8. The synergistic germicidal composition according to any one of Items 1 to 7, wherein the blending ratio of (A) the nitrophenol compound is 1 to 5000 parts by weight with respect to 100 parts by weight of (B) the bactericidal active ingredient .
  • Item 9. Item 9.
  • a method for controlling a pathogen which comprises treating the synergistic microbicidal composition according to any one of items 1 to 8 in a habitat (except for humans) of agricultural and horticultural pathogens.
  • Item 10. Item 9.
  • a method for controlling pathogens which comprises treating the synergistic germicidal composition according to any one of items 1 to 8 in the habitat of agricultural and horticultural pathogens.
  • Item 9. A plant protection method comprising treating the synergistic bactericidal composition according to any one of items 1 to 8 to a plant parasitic to agricultural and horticultural pathogens or its vicinity.
  • Item 12. Method of using a nitrophenol compound for enhancing bactericidal activity.
  • the bactericidal compounds are metalaxyl, metalaxyl M, boscalid, pyraclostrobin, azoxystrobin, trifloxystrobin, clesoxim methyl, picoxystrobin, spywareofamid, famoxadone, ametocutrazine, fluazinam, tetraconazole, oxosconazole Fumarate, flutriaphor, chlorothalonil, manzeb, dimethomorph, mandipropamide, etaboxam, acibenzolar-S-methyl, fluopicolide, propamocarb hydrochloride, fosetylaluminum, phosphorous acid or its salt, oxathiapiproline, nonylphenol sulfonic acid copper salt And at least one compound selected from the group consisting of and simoxanyl.
  • Item 14. The method according to item 12 or 13, wherein the nitrophenol compound is a phenol compound having one nitro group.
  • Item 15. A bactericidal activity enhancer containing a nitrophenol compound.
  • Item 16. It is a bactericidal activity enhancer containing a nitrophenol compound for a bactericidally active compound,
  • the bactericidal compounds are metalaxyl, metalaxyl M, boscalid, pyraclostrobin, azoxystrobin, trifloxystrobin, clesoxim methyl, picoxystrobin, spywareofamid, famoxadone, ametocutrazine, fluazinam, tetraconazole, oxosconazole Fumarate, flutriaphor, chlorothalonil, manzeb, dimethomorph, mandipropamide, etaboxam, acibenzolar-S-methyl, fluopicolide, propamocarb hydrochloride
  • the synergistic germicidal composition of the present invention is effective against agricultural and horticultural pathogens at low doses.
  • the synergistic bactericidal composition of the present invention exerts similarly excellent control effects even on agricultural and horticultural pathogens that have acquired resistance to existing bactericidal compounds.
  • the treatment dose can be reduced as compared with the case where each existing bactericidal agent is used alone, the agricultural and horticultural pathogens for each bactericidal compound can be reduced. It can also suppress the development of resistance.
  • synergistic Bactericidal Composition A synergistic germicidal composition (hereinafter sometimes referred to as "the composition of the present invention") containing the nitrophenol compound of the present invention and a germicidally active compound is described below.
  • Nitrophenol Compound (A) The nitrophenol compound is not particularly limited as long as it is an aromatic ring compound having one or more nitro groups and one or more hydroxyl groups (OH groups). Furthermore, you may have substituents other than the said nitro group and a hydroxyl group.
  • the substituent is not particularly limited, for example, a halogen atom, C 1 ⁇ 6 alkyl group, C 1 ⁇ 6 haloalkyl group, C 1 ⁇ 6 alkoxy group, C 1 ⁇ 6 haloalkoxy group, C 2 ⁇ 6 alkenyl group , C 2 ⁇ 6 haloalkenyl groups, C 2 ⁇ 6 alkenyloxy groups, C 2 ⁇ 6 haloalkenyloxy groups, C 2 ⁇ 6 alkynyl groups, C 2 ⁇ 6 haloalkynyl groups, C 2 ⁇ 6 alkynyloxy groups, C etc. 2-6 haloalkynyloxy group.
  • the nitrophenol compound in the present specification also includes a salt-formed nitrophenol compound (a salt of a nitrophenol compound).
  • salts in the present specification include alkali metal salts (sodium salt, potassium salt and the like), alkaline earth metal salts (calcium salt, magnesium salt and the like), ammonium salt (ammonia; morpholine, piperidine, pyrrolidine, lower mono, Di- or trialkylamines, organic amines such as lower mono-, di- or trihydroxyalkylamines, etc., and the like, and the like, preferably water-soluble, agrochemically advantageous salts, more preferably alkali metal salts. is there.
  • nitrophenol compound for example, the following general formula (1): (Wherein, X represents a C—R ′ group or a nitrogen atom. R, and R 'are the same or different, a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, C 1 ⁇ 6 alkyl group, C 1 ⁇ 6 haloalkyl group, C 1 ⁇ 6 alkoxy group, C 1 ⁇ 6 haloalkoxy groups, C 2 ⁇ 6 alkenyl groups, C 2 ⁇ 6 haloalkenyl groups, C 2 ⁇ 6 alkenyloxy groups, C 2 ⁇ 6 haloalkenyloxy groups, C 2 ⁇ 6 alkynyl groups, C 2 ⁇ 6 haloalkynyl groups, C 2-6 alkynyloxy group, or an C 2-6 haloalkynyl group. )
  • the nitrophenol compound or its salt etc. which are represented by these are mentioned.
  • nitrophenol compound the following general formula (2): (Wherein, R 1 , R 2 , R 3 , R 4 and R 5 groups are the same or different and are a hydrogen atom, a halogen atom, a hydroxyl group, a nitro group, a C 1-6 alkyl group, a C 1-6 haloalkyl groups, C 1 ⁇ 6 alkoxy groups, C 1 ⁇ 6 haloalkoxy groups, C 2 ⁇ 6 alkenyl groups, C 2 ⁇ 6 haloalkenyl groups, C 2 ⁇ 6 alkenyloxy groups, C 2 ⁇ 6 haloalkenyloxy groups, C 2-6 alkynyl group, C 2-6 haloalkynyl group, a C 2-6 alkynyloxy group, or a C 2-6 haloalkynyl group.)
  • the nitrophenol compound or its salt etc. which are represented by these are mentioned.
  • halogen atom for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom etc. are mentioned.
  • the C 1-6 alkyl group is not particularly limited, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, and n- Examples thereof include linear or branched alkyl groups having 1 to 6 carbon atoms such as pentyl group, isopentyl group, neopentyl group, n-hexyl group and isohexyl group. In the present specification, "n-" indicates normal, "s-" indicates secondary, and "t-" indicates tertiary.
  • the C 1-6 haloalkyl group is not particularly limited, and examples thereof include a fluoromethyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, a difluoromethyl group, a trifluoromethyl group, a 1-fluoroethyl group and a 2-fluoroethyl group.
  • the C 1-6 alkoxy group is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, an s-butoxy group, an s-butoxy group, and an n-butoxy group.
  • C1-C6 linear or branched alkoxy groups such as pentyloxy group, isopentyloxy group, neopentyloxy group, n-hexyloxy group and isohexyloxy group.
  • the C 1-6 haloalkoxy group is not particularly limited.
  • the C 2 ⁇ 6 alkenyl group is not particularly limited, for example, vinyl group, 1-propenyl group, allyl group, isopropenyl group, 1-butenyl, 2-butenyl, 3-butenyl group, 1-methyl - And C2-C6 linear or branched alkenyl groups such as 2-propenyl group and 1,3-butadienyl group.
  • the C 2 ⁇ 6 haloalkenyl group is not particularly limited, for example, 2,2-dichlorovinyl group, 2,2-dibromo-vinyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-Allyl group, 3,3-dichloro-2-allyl group, 4-chloro-2-butenyl group, 4,4,4-trifluoro-2-butenyl group, 4,4,4-trichloro-3-butenyl group, A linear or branched alkenyl group having 2 to 6 carbon atoms having at least one double bond at any position such as 5-chloro-3-pentenyl group, 6-fluoro-2-hexenyl group, etc. And alkenyl groups substituted with 1 to 13, preferably 1 to 7 halogen atoms.
  • the 2-6 alkenyloxy group is not particularly limited, for example, vinyloxy group, 1-propenyloxy group, allyloxy group, isopropenyloxy group, 1-butenyloxy, 2-butenyloxy, 3-butenyloxy group, 1 And C2-C6 linear or branched alkenyloxy groups such as -methyl-2-propenyloxy group and 1,3-butadienyloxy group.
  • the C 2 ⁇ 6 haloalkenyloxy group is not particularly limited, for example, 2,2-dichlorovinyl group, 2,2-dibromo-vinyl group, 3-chloro-2-propenyloxy group, 3,3 Difluoro-2-allyloxy group, 3,3-dichloro-2-allyloxy group, 4-chloro-2-butenyloxy group, 4,4,4-trifluoro-2-butenyloxy group, 4,4,4-trichloro-3 —C2-C6 linear or branched chain having at least one double bond at any position such as butenyloxy group, 5-chloro-3-pentenyloxy group, 6-fluoro-2-hexenyloxy group and the like
  • the C 2 ⁇ 6 alkynyl group include an ethynyl group, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl group, 1-butynyl group, 2-butynyl group, carbon atoms such as 3-butynyl group And 2 to 6 straight or branched chain alkynyl groups.
  • the 2-6 haloalkynyl group is not particularly limited, for example, 3,3,3-trifluoro-propynyl group, 3,3-difluoro-propynyl group, 3,3,3-trifluoro-butynyl group, 4, A linear or branched alkynyl group having 2 to 6 carbon atoms which has at least one triple bond at any position such as 4,4-trifluoro-2-butynyl group, 3,3-difluoro-butynyl group, etc. And an alkynyl group substituted with 1 to 13, preferably 1 to 7 halogen atoms.
  • the C 2 ⁇ 6 alkynyloxy group is not particularly limited, for example, ethynyl group, 1-propynyloxy group, 2-propynyl group, 1-methyl-2-propynyl group, 1-butynyloxy group, 2- Examples thereof include linear or branched alkynyloxy groups having 2 to 6 carbon atoms, such as butynyloxy group and 3-butynyloxy group.
  • the C 2 ⁇ 6 haloalkynyloxy group is not particularly limited, for example, 3,3,3-trifluoro-propynyl group, 3,3-difluoro-propynyloxy group, 3,3,3-trifluoro-butynyl-oxy Group, linear or branched having 2 to 6 carbon atoms having at least one triple bond at any position such as 4,4,4-trifluoro-2-butynyloxy, 3,3-difluoro-butynyloxy and the like
  • Examples of the alkynyloxy group include alkynyloxy groups substituted with 1 to 13, preferably 1 to 7 halogen atoms.
  • the aromatic ring compound is not particularly limited, and examples thereof include carbocyclic compounds such as benzene, naphthalene and anthracene; and heterocyclic compounds such as pyridine, pyrimidine, pyridazine, pyrazine and pyrazole.
  • X is preferably a C—R group.
  • R ' is a hydrogen atom, a halogen atom, is preferably from C 1 ⁇ 6 alkyl group or a C 1 ⁇ 6 alkoxy group, a hydrogen atom or a methoxy group More preferable.
  • R 1 is preferably a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group or a C 1-6 alkoxy group, A nitro group or a methoxy group is more preferred.
  • R 2 is preferably a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group or a C 1-6 alkoxy group, A nitro group or a methoxy group is more preferred.
  • R 3 is preferably a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group or a C 1-6 alkoxy group, A nitro group or a methoxy group is more preferred.
  • R 4 is preferably a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group or a C 1-6 alkoxy group, A nitro group or a methoxy group is more preferred.
  • R 5 is preferably a hydrogen atom, a halogen atom, a nitro group, a C 1-6 alkyl group or a C 1-6 alkoxy group, A nitro group or a methoxy group is more preferred.
  • nitrophenol compounds such as 4-nitrophenol, 4-nitrophenol sodium salt, 3-nitrophenol, 3-nitrophenol sodium salt, 2-nitrophenol, 2-nitrophenol sodium salt or salts thereof;
  • Particularly preferred are guaiacol (alias: guaiacol) compounds such as nitroguaiacol, 5-nitroguaiacol sodium salt, 4-nitroguaiacol, 4-nitroguaiacol sodium salt and the like or salts thereof.
  • the nitrophenol compound contained in the composition of the present invention is a known compound, and a commercially available product (Atonic (registered trademark)) or a compound produced by a known production method can be used.
  • the manufacturing method thereof is described, for example, in JP-A-10-67716.
  • the above atomic is an aqueous solution containing 4-nitrophenol (0.3%), 2-nitrophenol (0.2%) and 5-nitroguaiacol (0.1%).
  • the fungicidal compound contained in the composition of the present invention is not particularly limited as long as it is a compound known as a compound having a controlling effect on agricultural pests.
  • the composition of the present invention exerts the effects of the present invention, other pesticides, acaricides and fungicides can be appropriately used in combination as a pesticide.
  • the bactericidal active compound is not particularly limited, and, for example, A (nucleic acid synthesis), B (in the action classification by FRAC (Fungicide Resistance Action Committee) Mitotic division and cell division), C (respiration), D (amino acid and protein biosynthesis), E (signal transduction), F (lipid biosynthesis or transport / cell membrane structure or function), G (cell membrane sterol biosynthesis) ), H (cell wall biosynthesis), I (melanin biosynthesis of cell wall), P (resistance growth induction of host plant), M (multifunctional contact compound), U (action mechanism unknown), compounds not classified Etc.
  • A nucleic acid synthesis
  • B in the action classification by FRAC (Fungicide Resistance Action Committee) Mitotic division and cell division
  • C respiration
  • D amino acid and protein biosynthesis
  • E signal transduction
  • F lipid biosynthesis or transport / cell membrane structure or function
  • G cell membrane sterol biosynthesis
  • H cell wall biosynthesis
  • I melting induction of host plant
  • M multi
  • group A group A, group B, group C, group F, group G, group H, group M and group U are preferable, and the following group (A1), group (B1, 2, 3, B5), group (C2, C3, C4, C5, C8), group (F4, F9), group (G1), group (H5), group (M1, 3, 5), and group (U) are more preferable.
  • RNA polymerase inhibitor A1
  • A2 adenosine deaminase
  • A3 DNA / RNA biosynthesis inhibitor
  • DNA topoisomerase A4
  • RNA polymerase inhibitors include, for example, acylalanines such as benalaxyl (benalaxyl), benalaxyl M (benalaxyl-M), furalaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl M (metalaxyl-M), etc. ofurace etc. Butyrolactones; oxazolidinones such as oxadixyl; and the like.
  • Adenosine deaminase (A2) Examples of adenosine deaminase include hydroxy (2-amino-) pyrimidines such as bupirimate, dimethirimol, ethirimol and the like.
  • DNA / RNA biosynthesis inhibitor examples include isoxazoles such as hymexazole and isothiazolones such as octhilinone.
  • DNA topoisomerase examples include carboxylic acids such as oxolinic acid, and the like.
  • ⁇ B group> As group B (mitotic division and cell division), for example, ⁇ -tubulin polymerization inhibitor (B1, 2, 3), cell division inhibitor (B4), delocalizing agent of spectrin-like protein (B5) ), Inhibitors of actin, myosin and fimbrin functions such as vesicle transport (B6) and the like.
  • ⁇ -tubulin polymerization inhibitor (B1)
  • ⁇ -tubulin polymerization inhibitors include benzamyls such as benomyl, fuberidazole, carbendazim, thiabendazole, etc .; thiophanate, thiophanate methyl, etc. And thiophanates of
  • ⁇ -tubulin polymerization inhibitor B2
  • N-phenyl carbamates such as diethofencarb.
  • ⁇ -tubulin polymerization inhibitor examples include toluamides such as zoxamide; ethylaminothiazole carboxamides such as ethaboxam; and the like.
  • Cell division inhibitor (B4) examples include phenylureas such as pencycuron and the like.
  • Delocalization agent of spectrin-like protein (B5)
  • Examples of the delocalization agent for spectrin-like protein include pyridinylmethyl benzamides such as fluopicolide, and the like.
  • Inhibitors of actin, myosin and fimbrin functions such as vesicle transport (B6)
  • Examples of inhibitors of actin, myosin and fimbrin functions such as vesicle transport include aminocyanoacrylates such as phenamacril; benzophenones such as metrafenone; benzoylpyridines such as pyriofenone Can be mentioned.
  • ⁇ C group> As group C (respiratory), for example, respiratory chain complex I (NADH oxidase) inhibitor (C1), respiratory chain complex II (succinic acid dehydrogenase) inhibitor (C2), respiratory chain complex III (ubiquinol) Oxidase, Qo site) inhibitor (C3), respiratory chain complex III (ubiquinone reductase, Qi site) inhibitor (C4), uncoupling agent in oxidative phosphorylation (C5), inhibition of oxidative phosphorylation in ATP synthesis
  • the agent (C6), the ATP production inhibitor (C7), the respiratory chain complex III (ubiquinone reductase, Qo site) inhibitor (C8) and the like can be mentioned.
  • Respiratory chain complex I (NADH oxidase) inhibitor C1
  • respiratory chain complex I (NADH oxidase) inhibitors include pyrimidine amines such as diflumetrim; pyrazole carboxamides such as tolfenpyrad; quinazolines such as fenazaquin; and the like.
  • Respiratory chain complex II succinic acid dehydrogenase inhibitor (C2)
  • respiratory chain complex II (succinate dehydrogenase) inhibitors include phenylbenzamides such as benodanil, flutolanil, mepronil and the like; phenyloxoethylthiophene amides such as isofetamide and the like Pyridinylethyl benzamides such as fluopyram; furancarboxamides such as fenfuram; oxathiin carboxamides such as carboxin, oxicarboxin etc .; thifluzamide etc Thiazolecarboxamides; benzobindiflupyr (benzovindiflupyr), bixafen (bixafen), fluindapyr (fluindapyr), fluxapyroxad (fluxapyroxad), furametopyr (furametpyr), isopyrazam, penflufen, penflufen, isopyra
  • Respiratory chain complex III (Ubiquinol oxidase, Qo site) inhibitor (C3)
  • a respiratory chain complex III (ubiquinol oxidase, Qo site) inhibitor for example, azoxystrobin (azoxystrobin), picoxystrobin (picoxystrobin), enoxastrobin (enoxastrobin), pyroxystrobin (pyraoxystrobin), Methoxy acrylates such as coumoxystrobin, fluphenoxystrobin, etc .; methoxyacetamides such as mandestrobin, etc .; orysastrobin (orysastrobin), dimoxystrobin (dimoxystrobin), metominostrobin ( Metominosstrobin), oxaminamides such as phenaminstrobin (fenaminstrobin); Pyraclostrobin, pyrametostrobin, methoxycarbamates such as triclopyricarb (cresoximmeth) (Kresoxim-methyl), oxi
  • Respiratory chain complex III ubiquinone reductase, Qi site
  • a respiratory chain complex III ubiquinone reductase, Qi site
  • cyanoimidazole such as cyazofamid (cyazofamid)
  • sulfamoyltriazole such as amisulbrom
  • picolinamides such as fenpicoxamide And Ferimsone etc.
  • Uncoupling agent (C5) in oxidative phosphorylation examples include 2,6-dinitroanilines such as fluazinam; dinitrophenyl crotonic acids such as meptyl dinocap; binapacryl; ferimzone Etc.), and the like.
  • Inhibitors of oxidative phosphorylation in ATP synthesis include triphenyltin compounds such as fentin acetate, fentin chloride, fentin hydroxide and the like.
  • ATP production inhibitor examples include thiophenecarboxamides such as silthiofam and the like.
  • Respiratory chain complex III ubiquinone reductase, Qo site
  • a respiratory chain complex III ubiquinone reductase, Qo site
  • triazolopyrimidylamine such as ametoctradin and the like, and the like
  • D group amino acid and protein biosynthesis
  • D1 methionine biosynthesis inhibitor
  • D2, 3, 4, 5 protein synthesis inhibitor
  • Methionine biosynthesis inhibitor (D1) examples include anilinopyrimidines such as cyprodinil, mepanipyrim, pyrimethanil and the like.
  • Protein synthesis inhibitor (D2) examples include enopyranuronic acid antibiotics such as blasticidin S (blasticidin-S) and the like.
  • Protein synthesis inhibitor (D3) examples include hexopyranosyl antibiotics such as kasugamycin and the like.
  • Protein synthesis inhibitor (D4) examples include glucopyranosyl antibiotics such as streptomycin, and the like.
  • Protein synthesis inhibitors include, for example, tetracycline antibiotics such as oxytetracycline.
  • E signal transduction inhibitor with unknown mechanism
  • E2 MAP ⁇ histidine kinase
  • E3 MAP ⁇ histidine in osmotic signaling Kinase inhibitors
  • Signal transduction inhibitor of unknown mechanism examples include allyloxyquinolines such as quinoxyfen and the like; quinazolinones such as proquinazid and the like.
  • MAP ⁇ Histidine kinase (os-2, HOG1) (E2) in osmotic signaling examples include phenylpyrroles such as fenpiclonil, fludioxonil, and the like.
  • MAP and histidine kinase inhibitors (os-1, Daf1) E3 in osmotic signaling
  • MAP and histidine kinase inhibitors (os-1, Daf1) in osmotic signaling for example, clozolinate (chlozolinate), procymidone (procymone), isoprodione (isoprodione), vinclozolin, vinclozolin, dimethaclone, etc.
  • Dicarboximides and the like can be mentioned.
  • F group structure or function of lipid biosynthesis or transport / cell membrane
  • F2 methyltransferase inhibitors of phospholipid biosynthesis
  • F3 lipid peroxidation inhibitors
  • F4 cell membrane-permeant fatty acids
  • F6 Microbial disturbance of pathogen cell membrane
  • F7 cell membrane disrupter
  • F8 ergosterol binder
  • F9 lipid homeostasis
  • Methyltransferase inhibitors (F2) of phospholipid biosynthesis examples include phosphorothiolates such as pyrazophos, edifenphos, iprobenfos and the like; dithiolanes such as isoprothiolane and the like Etc.
  • Lipid Peroxidation Inhibitor examples include aromatic hydrocarbons such as tecnazen, dichloran, quintozene, biphenyl, tolclofos-methyl, chloroneb, etc. And 1,2,4-thiadiazoles such as etridiazole.
  • Cell membrane permeable fatty acid examples include carbamates such as prothiocarb, iodocarb, propamocarb, propamocarb hydrochloride salt and the like.
  • Microbial perturbation of pathogen cell membranes include, for example, Bacillus genus such as Bacillus amyloliquefaciens (synonym Bacillus subtilis) strains: QSR 713 FZB24 MBI 600 D747 and produced bactericidal lipopeptides.
  • Cell membrane disruptor As disrupters of cell membranes, for example, terpenoid compounds such as eugenol (eugenol), geraniol (geraniol), thymol (thymol), plant extracts containing these compounds, terpene hydrocarbons such as essential oils, and terpene alcohols And terpene phenols.
  • terpenoid compounds such as eugenol (eugenol), geraniol (geraniol), thymol (thymol), plant extracts containing these compounds, terpene hydrocarbons such as essential oils, and terpene alcohols And terpene phenols.
  • Ergosterol binder examples include amphoteric amphiphilic macrolide antifungal antibiotics produced by actinomycetes Streptomyces natalensis or S. chattanoogensis such as natamycin (natamycin).
  • Inhibitors of lipid homeostasis, metastasis, storage F9
  • Examples of the inhibitor of lipid homeostasis, transfer and storage include piperidinylthiazole isoxazolines such as oxathiapiproline and the like.
  • G group sterol biosynthesis of cell membrane
  • G1 sterol biosynthesis of cell membrane
  • G2 sterol biosynthesis of cell membrane
  • G3 3-ketoreductase inhibitors
  • G4 inhibitors of squalene epoxidase
  • Inhibitors of C14 demethylation in sterol biosynthesis examples include azaconazole (azaconazole), bitertanol (bitertanol), bromuconazole (bromuconazole), cyproconazole (cyproconazole), difenoconazole (difenoconazole), diniconazole (diniconazole) ), Epoxiconazole (epoxiconazole), etaconazole (etaconazole), fenbuconazole (fenbuconazole), fluquinconazole (fluquinconazole), flusiazole (flusilazole), flutriahol (flutriafol), hexaconazole (hexaconazole), imibenconazole (Imibenzonazole), ipconazole (ipconazole), metconazole (metconazole)
  • ⁇ 14 Reductase and ⁇ 8 ⁇ ⁇ 7 Isomerase (G2) in Sterol Biosynthesis examples include morpholinins such as aldimorph, fenpropimorph, tridemorph and dodemorph; fenpropidin, And piperidines such as piperalin; spiroketal amines such as spiroxamine and the like.
  • 3-ketoreductase inhibitors in C4 demethylation
  • 3-ketoreductase inhibitors in demethylation at the C4 position include hydroxyanilides such as fenhexamid; aminopyrazolinones such as fenpyrazamine.
  • Inhibitors of squalene epoxidase in sterol biosynthesis examples include thiocarbamates such as naftifine and terbinafine; and thiocarbamates such as pyributicarb.
  • H group cell wall biosynthesis
  • H4 chitin biosynthesis inhibitors
  • H5 cellulose synthesis inhibitors
  • Chitin biosynthesis inhibitor examples include peptidyl pyrimidine nucleosides such as polyoxin B (polyoxine B) and the like.
  • Cellulose synthesis inhibitors include, for example, dimethomorph, flumorph, cinnamic acid amides such as pyrimorph, etc .; mandelic acid amides such as mandipropamide, etc .; iprovalicarb; (Benthiavalicarb), valine amide carbamates such as valifenacarb (valifenalate) and the like.
  • group I melanin biosynthesis in cell walls
  • reductase inhibitor (I1) in melanin biosynthesis
  • dehydratase inhibition in melanin biosynthesis I2
  • polyketide synthesis inhibition in melanin biosynthesis I3
  • Reductase inhibitors in melanin biosynthesis examples include isobenzofuranones such as phthalide; pyrroloquinolinones such as pyroquilon; and triazolobenzothiazoles such as tricyclazole.
  • Dehydration enzyme inhibition in melanin biosynthesis examples include carboxamides such as diclocymet; cyclopropanecarboxamides such as carpropamide; propionamides such as fenoxanil and the like.
  • Polyketide synthesis inhibitor in melanin biosynthesis examples include trifluoroethyl carbamates such as tolprocarb, and the like.
  • ⁇ M group> Compounds that target multiple action points (M)
  • compounds (M) targeted to multiple action points include copper compounds (M1), sulfur compounds (M2), dithiocarbamate compounds and their related compounds (M3), phthalimide compounds (M4), chloronitriles Compounds (M5), sulfamide compounds (M6), bisguanidine compounds (M7), triazine compounds (M8), anthraquinone compounds (M9), quinoxaline compounds (M10), maleimide compounds (M11), etc. It can be mentioned.
  • Preferred compounds (M) targeted for multiple action points are M1, M3 and M5.
  • Copper compound (M1) As the copper compound, for example, inorganic compounds such as DBEDC, basic copper chloride (copper oxychloride), basic copper sulfate (copper sulfate), copper hydroxide (copper hydroxide), copper nonylphenol sulfonate (copper nonylphenol sulfonate), etc. (Does not contain sulfur) and the like.
  • inorganic compounds such as DBEDC, basic copper chloride (copper oxychloride), basic copper sulfate (copper sulfate), copper hydroxide (copper hydroxide), copper nonylphenol sulfonate (copper nonylphenol sulfonate), etc. (Does not contain sulfur) and the like.
  • Sulfur based compounds As a sulfur type compound, inorganic compounds (it does not contain copper), such as sulfur (sulfur) and a lime sulfur compound (lime sulfur), etc. are mentioned, for example.
  • Dithiocarbamate compounds and related compounds examples include ferbam, metiram, thiram, manzeb (mancozeb), propineb (propineb), zineb (zineb), zinc thiazole (zinc thiazole), and the like. And dithiocarbamates and analogs such as maneb ziram.
  • Phthalimide compound (M4) examples include phthalimides such as captan, captafol, and folpet.
  • Chloronitrile compound (M5) examples include chloronitriles (phthalonitriles) such as chlorothalonil and the like.
  • Sulfamide compounds M6
  • Examples of the sulfamide compounds include sulfamides such as dichlofluanid and tolylfluanid.
  • Bisguanidine compound (M7) examples include bisguanidines such as guazatine and iminoctadine.
  • Triazine-based compounds (M8) As a triazine type compound, triazines, such as anilazine (anilazine), etc. are mentioned, for example.
  • Anthraquinone compound (M9) Examples of anthraquinone compounds include quinones (anthraquinones) such as dithianon (dithianon) and the like.
  • quinoxaline compounds examples include quinoxalines such as quinomethionate and quinomethionate.
  • maleimide compound (M11) examples include maleimide compounds (M11) such as fluoroimide.
  • thiocarbamate compound examples include thiocarbamates such as metasulfocarb and the like.
  • P group resistance plant life inducer of host plant
  • resistance inducer which stimulates salicylic acid pathway (P1)
  • resistance plant inducer of host plant P2, 3, 4
  • resistance of host plant Plant extracts P5 to be induced
  • microorganisms and microorganism preparations P6 to induce resistance of host plants, and the like
  • Resistance inducer which stimulates the salicylic acid pathway
  • resistance inducers salicylic acid signaling
  • benzothiadiazole BTH such as acibenzolar-S-methyl
  • Host plant resistance inducer P2
  • Examples of resistance inducers for host plants include benzisothiazoles such as probenazole and the like.
  • Host plant resistance inducer P3
  • Examples of resistance inducers for host plants include thiadiazole carboxamides such as isothianyl, thiazinyl, and the like.
  • Host plant resistance inducer P4
  • Examples of resistance inducers for host plants include polysaccharides such as laminarin, and the like.
  • Plant extract (P5) which induces resistance of host plant
  • plant extracts anthraquinone elicitors, plant extracts
  • plant extracts that induce resistance of host plants
  • extracts of plants of the genus Reynoutria Oitadori
  • Reynoutria sachalinensis Giant knotweed
  • essential oils etc.
  • Microorganisms and microbial preparations that induce resistance of host plants include Bacillus cereus such as Bacillus mycoides or preparations thereof.
  • Inducers of host plant resistance examples include ethylphosphonates such as fosetyl, fosetyl-al, etc .; phosphorous acids, phosphites, etc. .
  • cyanoacetamide oxime such as cymoxanil; phthalamic acid such as teclofthalam; phenylacetamide such as cyflufenamide etc .; fluthianil (fluthianil)
  • Cyanomethylene thiazolidines acetic acid 4-quinoline such as tebufloquin; glucopyranosyl antibiotics such as validamycin; benzotriazines such as triazoloxide; benzenesulfonamides such as flusulfamide; dichromedines Pyridazinones such as (diclomezine); guanidines such as dodine; tetrazolyl oxime such as picarbutrazox and the like.
  • more preferable bactericidal agents are metalaxyl, metalaxyl M, boscalid, pyraclostrobin, azoxystrobin, trifloxystrobin, clesoxim-methyl, picoxystrobin, ciazofamid, famoxadone, ametocutrazine, fluazinam, tetraconazole, oxospoco Nazole fumaric acid salt, flutriaphor, chlorothalonil, manzeb, dimethomorph, mandipropamide, etaboxam, fluopicolide, propamocarb hydrochloride, fosetyl aluminum, phosphorous acid or its salt, oxathiapiproline, nonylphenol sulfonic acid copper salt and shimoxanyl.
  • synergistic bactericidal composition a bactericidal composition having a synergistic control effect (synergistic effect).
  • the bactericidally active compound is usually 0.1 to 20000 parts by weight, preferably 1 to 10000 parts by weight, more preferably 5 to 5000 parts by weight based on 100 parts by weight of the nitrophenol compound of the general formula (1). Mix.
  • the nitrophenol compound and the bactericidal active compound may be simply added without adding other components, but usually, a solid carrier, a liquid carrier and a gaseous carrier (propellant) are mixed and necessary.
  • a solid carrier usually, a liquid carrier and a gaseous carrier (propellant) are mixed and necessary.
  • surfactants and other pharmaceutical auxiliaries according to the formulation and formulate into oil, emulsion, wettable, flowable, granules, powder, aerosol, aerosol etc according to the usual formulation method Good to use.
  • the total amount of the nitrophenol compound as an active ingredient and the bactericidal active compound is usually contained in an amount of 0.01 to 95% by weight, preferably 0.1 to 50% by weight.
  • solid carriers used in formulation include clays (kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, hubashi clay, acid clay etc), talcs, ceramics, other inorganic minerals (celite, quartz, Fine powders or particles of sulfur, activated carbon, calcium carbonate, hydrated silica, etc., chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, sodium chloride etc.) and the like can be mentioned.
  • clays kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, hubashi clay, acid clay etc
  • talcs ceramics
  • other inorganic minerals celite, quartz, Fine powders or particles of sulfur, activated carbon, calcium carbonate, hydrated silica, etc.
  • chemical fertilizers ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, sodium chloride etc.
  • liquid carrier examples include water, alcohols (methanol, ethanol etc.), ketones (acetone, methyl ethyl ketone etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methyl naphthalene etc.), aliphatic hydrocarbons (Hexane, cyclohexane, kerosene, light oil etc.), esters (ethyl acetate, butyl acetate etc.), nitriles (acetonitrile, isobutyronitrile etc.), ethers (diisopropyl ether, dioxane etc.), acid amides (N , N-dimethylformamide, N, N-dimethylacetamide and the like), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride and the like), vegetable oils such as dimethylsulfoxide, soybean oil, cotton,
  • gaseous carrier examples include butane gas, LPG (liquefied petroleum gas), dimethyl ether, carbon dioxide gas and the like.
  • alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives, etc. can be mentioned.
  • a sticking agent As a formulation adjuvant, a sticking agent, a dispersing agent, a stabilizer etc. are mentioned, for example.
  • the fixing agent and / or the dispersing agent for example, casein, gelatin, polysaccharide (starch powder, gum arabic, cellulose derivative, alginic acid etc.), lignin derivative, bentonite, saccharide, synthetic water-soluble polymer (polyvinyl alcohol, polyvinyl pyrrolidone) And polyacrylic acids, etc.).
  • the stabilizer for example, PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4-methoxyphenol and 3-tert- (Butyl 4-methoxyphenol mixture), vegetable oil, mineral oil, fatty acid or ester thereof and the like.
  • the disinfectant of the present invention may be used as it is or diluted with water or the like. It is also used simultaneously with or without mixing with other insecticides, nematocides, acaricides, fungicides, herbicides, plant growth regulators, synergists, soil conditioners, animal feed etc. It can also be done.
  • composition of the present invention When the composition of the present invention is used as an agricultural bactericide, its application amount is usually 0.1 g to 500 g, preferably 1 to 100 g, per 1000 m 2 .
  • present synergistic germicidal composition of the present invention in the form of emulsion, wettable powder, flowable and the like is used after dilution with water, its application concentration is usually 1 to 1000 ppm, preferably 10 to 500 ppm. Powders and the like are applied as they are, without dilution.
  • the application concentration of the nitrophenol compound is usually about 0.5 to 800 ppm, preferably about 12.5 to 400 ppm, more preferably about 100 to 200 ppm, and the application concentration of the bactericidal compound is usually 0.1 to It is about 200 ppm, preferably about 0.1 to 50 ppm, and more preferably about 0.4 to 20 ppm.
  • the nitrophenol compound and the bactericidal active compound are contained to explain the use thereof, but a composition separately containing the nitrophenol compound and the bactericidal active compound is prepared.
  • these two compositions may be used sequentially or simultaneously, preferably simultaneously, in controlling agricultural and horticultural pathogens.
  • the nitrophenol compound and the bactericidal compound may be used in combination in the same proportion as described above.
  • the synergistic fungicidal composition of the present invention can control plant diseases caused by fungi, eubacteria and plant viruses depending on the application form.
  • the eubacteria that the synergistic microbicidal composition of the present invention can control include, for example, pathogens belonging to the following genera.
  • Burkholderia spp. Rice blight (Burkholderia gladioli), Rice seedling bacterial blight (Burkholderia plantarii);
  • Erwinia spp. Japanese radish soft rot Erwinia carotovora spp. Carotovora
  • Pseudomonas for example, Cucumber spot bacterial blight (Pseudomonas syringae pv. Lachrymans), Radish black spot blight (Pseudomonas syringae pv. Maculicola), Chinese cabbage black spot blight (Pseudomonas cannabina pv.
  • Citri Rhinovorax
  • Acidovorax for example, Watermelon fruit stain bacterial disease
  • Acidovorax avenae spp. Citrulli Watermelon fruit stain bacterial disease
  • Rice brown stripe disease Acidovorax avenae spp. Avenae
  • Clavibacter for example, Tomato scab (Clavibacter michiganensis spp. Michiganensis
  • Streptomyces for example, Potato scum disease (Streptomyces scabies) Etc.
  • Fungi that can be controlled by the synergistic fungicidal composition of the present invention include, for example, pathogens belonging to the following genus.
  • Alternaria spp. Black spot disease of cabbage (Alternaria brassicae), Cabbage scab (Alternaria brassicicola), Potato scab (Alternari solani), Chinese cabbage black spot (Alternaria brassicae, Alternaria brassicicola), Pumpkin black spot (Alternaria cucumerina), Eggplant brown spot (Alternaria solani), Cucumber black spot (Alternaria cucumerina), Apple spotted leaf blight (Alternaria alternata), Carrot black leaf blight (Alternaria dauci), Carrot black spot (Alternaria radicina), Strawberry black spot (Alternaria alternata), Black spot (Alternaria porri) onion, Pear black spot (Alternaria kikuchiana), Onion black spot (Alternaria sp.), Spring onion (Alternaria porri); For example, Aureobasidium spp.
  • Botrytis for example, Strawberry gray mold (Botrytis cinerea), Onion germicidal rot (Botrytis squamosa), Onion gray rot (Botrytis allii), Chinese cabbage leaf blight (Botrytis byssoidea), Green onions (Botrytis squamosa); Colletotrichum spp., For example, Wheat anthracnose (Colletotrichum graminicola), Potato anthracnose (Colletotrichum atramentarium), Komatsuna anthrax (Colletotrichum higginsianum), Azuki Anthracnose (Colletotrichum phaseolorum), Tea anthracnose (Colletotrichum theae-sinensis), Bean bean anthracnose (Colletotrichum lindemuthiamum), Soybean anthracnose (Colletotrichum truncatum), Spinach anthracnose (Colletotrichum graminicola), Potato anthracnose (Col
  • Apple ring leaf blight (Cristulariella moricola); Diplocarpon, for example, Apple brown spot (Diplocarpon mali), Rose scab (Diplocarpon rosae); For example, Diaporthe spp. Citrus sunspot (Diaporthe citri); For example, Elsinoe spp. Grapevine rot (Elsinoe ampelina), Citrus scab (Elsinoe fawcettii); Erysiphe, for example, Barley powdery mildew (Erysiphe graminis f. Sp. Tritici), Wheat powdery mildew (Erysiphe graminis f. Sp.
  • Cucumerinum Melon vines (Fusarium oxysporum f. Sp. Melonis); Fulvia, for example, Tomato leaf mold (Fulvia fulva); Fusicladium genus bacteria, for example, Persimmon scab (Fusicladium levieri); Gaeumannomyces genus bacteria, for example, Rice blight (Gaeumannomyces graminis var. Graminis), Barley dwarf (Gaeumannomyces graminis var.
  • Tritici Gibberella genus bacteria, for example, Rice fool seedling disease (Gibberella fujikuroi), Peach scab (Gibberella zeae); Glomerella genus bacteria, for example, Plum anthracnose (Glomerella cingulata), Ume leaf anthracnose (Glomerella mume), Sweet cherry anthrax (Glomerella cingulata), Grape late rot (Glomerella cingulata), Apple anthrax (Glomerella cingulata), Persimmon fruit disease (Glomerella sp.), Pear anthracnose (Glomerella cingulata), Persimmon leaf anthracnose (Glomerella cingulata), Strawberry anthrax (Glomerella cingulata), Chestnut anthrax (Glomerella cingulata); Gloesporium genus bacteria, for example, Oyster
  • Pleospora for example, Onion leaf blight (Pleospora herbarum), Red clover leaf blight (Pleospora herbarum), Apple brown leaf blight (Pleospora herbarum); Phakopsora genus bacteria, for example, Soybean rust (Phakopsora pachyrhizi); Phomopsis spp., For example, Asparagus stem blight (Phomopsis asparagi), Persimmon sunspot (Phomopsis kakivora); Phyllactinia, for example, Pear powdery mildew (Phyllactinia mali), Pear powdery mildew (Phyllactinia pyri); Phyllosticta, for example, Azuki bean brown rot (Phyllosticta phaseolina), Strawberry ring blight (Phyllosticta fragariicola), Japanese plum blight (Pyllosticta mume); Phy
  • Rhizopus for example, Sweet potato scab (Rhizopus nigricans), Peach black mold (Rhizopus nigricans), Cucumber seedling blight (Rhyzoctonia solani); Rhizoctonia spp., For example, Rice sheath blight (Rhizoctonia solani); For example, Rosellinia sp.
  • Ume white scab (Rosellinia necatrix); For example, Oyster soot disease (Scorias communis), Yamamomo soot disease (Scorias cylindrica); Sphaceloma spp., For example, Japanese sweet potato scum (Sphaceloma pruni-domesticae), Pomegranate scum disease (Sphaceloma punicae), Peanut scab (Sphaceloma arachidis); Sphaerotheca genus bacteria, for example, Ume powdery mildew (Sphaerotheca pannosa), Watermelon powdery mildew (Sphaerotheca fuliginea); Stenella spp., For example, Peach scab (Stenella sp.); Sptoria spp, for example, Black onion blight (Septoria alliacea), Strawberry scab (Septoria fragariae), Sweet potato scab (Sept
  • Grape powdery mildew (Uncinula necator); For example, Verticillium spp. Strawberry wilt (Verticillium dahliae); Venturia, for example, Pear scab (Venturia pirina), Pear scab (Venturia nashicola), Apple scab (Venturia inaequalis); For example, Zygophiala spp. Apple soot blight (Zygophiala jamaicensis), Oyster scum disease (Zygophiala jamaicensis) Etc.
  • a plant virus which can be controlled by the synergistic bactericidal composition of the present invention It is not particularly limited, and examples thereof include Tobamo virus genus, Potex virus genus, Calla virus genus, Cucumovirus type, Calmovirus genus and the like.
  • Tobamovirus genus virus for example, Tobacco mosaic virus (Tobacco mosaic virus, TMV), Tomato mosaic virus (Tomato mosaic virus, ToMV), Cucumber green mottle mosaic virus (Kyuri green mottle mosaic virus, KGMMV), Pepper milled mottle virus (Pepper mild mottle virus, PMMoV), Watermelon green mottle mosaic virus (Cucumber green mottle mosaic virus, CGMMV) etc.
  • TMV Tobacco mosaic virus
  • Tomato mosaic virus Tomato mosaic virus
  • ToMV Cucumber green mottle mosaic virus
  • KGMMV Cucumber green mottle mosaic virus
  • PMMoV Pepper milled mottle virus
  • Watermelon green mottle mosaic virus Cucumber green mottle mosaic virus, CGMMV
  • potex virus genus virus for example, Planago mosaic virus (Plantago asiatica mosaic virus, PlAMV), Potato X virus (Potato virus X, PVX) etc. are mentioned.
  • Potato mosaic virus As a virus of the genus Carla virus, Potato mosaic virus (Potato virus M, PVM) etc. are mentioned.
  • Cucumoviruses include: Cucumber mosaic virus (Cucumber mosaic virus, CMV) etc. are mentioned.
  • carmovirus genus virus for example, Melon necrotic spot virus (Melon necrotic spot virus, MNSV) etc. are mentioned.
  • useful plants for which the synergistic fungicidal composition of the present invention can be used include grains such as rice, barley, wheat, rye, oats and corn; soybeans, red beans, broad beans, peas and beans Beans such as beans and peanuts; Fruits and fruits such as apples, citrus fruits, pears, persimmons, peaches, plums, cherry blossoms, walnuts, chestnuts, almonds, bananas, strawberries, etc .; Leaves, fruits and vegetables such as cabbage, tomato, spinach, broccoli, lettuce, onion, green onion, green pepper, eggplant, pepper and the like; Carrot, potato, sweet potato, taro, radish, lotus root, turnip, burdock, garlic etc root vegetables; Processing crops such as cane, hemp, beets, hops, sugar cane, sugar beet, olives, gum, coffee, tobacco, tea, etc .; Uri species such as pumpkin, cucumber, mackerel, watermelon, melon;
  • the synergistic bactericidal composition of the present invention can protect the above plants by treating such agricultural / horticultural pathogens in the habitat or a plant parasitic to the agricultural / horticultural pathogens or in the vicinity thereof.
  • the habitat of the pest or the plant or its vicinity where the pest infests refers to the vegetation, especially stems, leaves, seeds, bulbs or seeds (hereinafter referred to as seeds, bulbs or seeds) simply as seeds, in which the pest to be controlled is infested It can be applied to fruits, etc.
  • Application methods include, for example, spraying on leaves or stems, or spraying, seed treatment (eg, seed soaking of soaked seeds or granules, etc.), soil application (eg, intercostal spraying or interval spraying of granules, etc.) Etc.).
  • nitrophenol compound can enhance its bactericidal activity by being added to a known germicide. That is, nitrophenol compounds can be used to enhance bactericidal activity.
  • Reference preparation example 1 10 parts of each of the composition of the present invention is dissolved in 45 parts of Solvesso 150 and 35 parts of N-methylpyrrolidone, 10 parts of an emulsifier (trade name: Sorpol 3005X, manufactured by Toho Chemical Co., Ltd.) is added thereto, and mixed by stirring. Each 10% emulsion was obtained.
  • Sorpol 3005X trade name: Sorpol 3005X, manufactured by Toho Chemical Co., Ltd.
  • Reference preparation example 2 (wettable powder) Twenty parts of each of the composition of the present invention is added to 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of synthetic hydrous silicon oxide fine powder and 54 parts of clay and mixed by stirring with a juice mixer. % Wettable powder was obtained.
  • Reference Preparation Example 3 Two parts of sodium dodecylbenzene sulfonate, 10 parts of bentonite and 83 parts of clay were added to 5 parts of each of the composition of the present invention and thoroughly mixed. The applied amount of water was added, and the mixture was further stirred, granulated with a granulator and blow-dried to obtain 5% granules.
  • Reference preparation example 4 1 part of each of the composition of the present invention is dissolved in an appropriate amount of acetone, 5 parts of synthetic hydrous silicon oxide fine powder, 0.3 parts of isopropyl acid phosphate (PAP) and 93.7 parts of clay are added thereto, and a juice mixer The mixture was stirred and mixed, and acetone was removed by evaporation to obtain 1% powder.
  • PAP isopropyl acid phosphate
  • Reference preparation example 5 (flowable agent) Twenty parts of each of the composition of the present invention, 3 parts of polyoxyethylene tristyryl phenyl ether phosphate ester triethanolamine, and 20 parts of water containing 0.2 parts of Rhodorsil 426R are mixed and wet-milled using a dyno mill, It was mixed with 60 parts of water containing 8 parts of propylene glycol and 0.32 parts of xanthan gum to obtain a 20% suspension in water.
  • Formulation B 0.9 part of 4-nitrophenol sodium salt (manufactured by Asahi Chemical Industry Co., Ltd.) was dissolved in 999.1 parts of water to prepare a water solvent. This water solvent is hereinafter referred to as "formulation B".
  • Formulation C A water solvent was prepared by dissolving 0.6 part of 2-nitrophenol sodium salt (manufactured by Asahi Chemical Industry Co., Ltd.) in 999.4 parts of water. This water solvent is hereinafter referred to as "Formulation C".
  • Preparation D 0.3 part of 5-nitro guaiacol sodium salt (manufactured by Asahi Chemical Industry Co., Ltd.) was dissolved in 999.7 parts of water to prepare a water solvent. This water solvent is hereinafter referred to as "Formulation D”.
  • Preparation E Naria (registered trademark) WDG (a water dispersible powder containing 6.8% by weight of pyraclostrobin and 13.6% by weight of boscalid) manufactured by BASF Agro Co., Ltd. is prepared as a water dispersible powder containing pyraclostrobin and boscalid. did. This preparation is referred to as "formulation E”.
  • Formulation F As a flowable agent containing fluazinam, Freonside (registered trademark) SC (a flowable agent containing 39.5% by weight of fluazinam) manufactured by BASF Agro Co., Ltd. was prepared. This preparation is referred to as "formulation F”.
  • Formulation G As a flowable agent containing picoxystrobin, Major (registered trademark) flowable (a flowable agent containing 22.5% by weight of picoxystrobin) manufactured by Japan Pesticides Co., Ltd. was prepared. This preparation is referred to as "formulation G".
  • Formulation H As a flowable agent containing cyazofamide, Lanman (R) flowable (a flowable agent containing 9.4% by weight of cyanophamide) manufactured by Ishihara Biosciences Co., Ltd. was prepared. This preparation is referred to as "formulation H".
  • Formulation I Horison (registered trademark) DF agent (DF agent containing 22.5% by weight of famoxadone and 30% by weight of shimoxanil) manufactured by Nissan Chemical Industries, Ltd. was prepared as a DF agent containing famoxadone and shimoxanil. This preparation is referred to as "formulation I”.
  • Formulation J As a flowable agent containing trifloxystrobin, Flint.RTM. Flowable 25 (a flowable agent containing 25% by weight of trifloxystrobin) manufactured by Bayer CropScience was prepared. This preparation is referred to as "formulation J".
  • Formulation K As a wettable powder containing chlorothalonil, Daconil (registered trademark) 1000 (a wettable powder containing 40% by weight of chlorothalonil) manufactured by Sumitomo Chemical Co., Ltd. was prepared. This preparation is referred to as "formulation K".
  • Formulation L Propose (registered trademark) water dispersible granule manufactured by Kumiai Chemical Industries Co., Ltd. as a water dispersible granule containing bench avaliculum and chlorothalonil (a water dispersible granule containing 5% by weight of bench alkaline carb and 50% by weight of chlorothalonil) Prepared. This preparation is referred to as "formulation L”.
  • Formulation M Strobie (registered trademark) DF (DF agent containing 50% by weight of kresoxim methyl) manufactured by Nissan Chemical Industries, Ltd. was prepared as a DF agent containing kresoxim methyl. This preparation is referred to as "formulation M”.
  • Formulation N 560 parts by weight of potassium dihydrogen phosphite was dissolved in 440 parts of pure water to make a total of 1000 parts by weight. This preparation is referred to as "formulation N".
  • Etofin registered trademark
  • Formulation O a flowable containing Etabaxam
  • Formulation P As a flowable agent containing amethocutrazine and dimethomorph, ZANPRO (registered trademark) DM flowable (a flowable agent containing 27% by weight of ametocutrazine and 20.3% by weight of dimethomorph) manufactured by BASF Agro Co., Ltd. was prepared. This preparation is referred to as "formulation P".
  • Formulation Q Festival (trademark) C wettable powder made by Hokuko Chemical Industry Co., Ltd. as a wettable powder containing dimethomorph and basic copper chloride (wettable powder containing 15% by weight dimethomorph, 58.8% by weight basic copper chloride) Prepared. This preparation is referred to as "formulation Q".
  • Formulation R As a flowable agent containing azoxystrobin, Amister (registered trademark) 20 flowable (a flowable agent containing 20% by weight of azoxystrobin) manufactured by Syngenta Japan Co., Ltd. was prepared. This preparation is referred to as "formulation R".
  • Preparation S As a wettable powder containing manzeb, Dimandaisen (registered trademark) wettable powder (a wettable powder containing 80% by weight of manzeb) manufactured by Dow Chemical Japan Ltd. was prepared. This preparation is referred to as "formulation S".
  • Formulation T Arietti (R) wettable powder (a wettable powder containing 80% by weight) manufactured by Bayer CropScience Co., Ltd. was prepared as a wettable powder containing fosetyl aluminum. This preparation is referred to as "formulation T”.
  • Formulation U As a flowable agent containing fluopicolide and propamocarb hydrochloride, Reliable (registered trademark) flowable (a flowable agent containing 5.5% by weight of fluopicolide and 55.5% of propamocarb hydrochloride) manufactured by Bayer CropScience Co., Ltd. was prepared. This preparation is referred to as "formulation U".
  • Formulation V Yonepon (a solution containing 30% by weight of nonylphenol sulfonic acid copper salt) manufactured by OAT Agrio Co., Ltd. was prepared as a solution containing nonylphenol sulfonic acid copper salt. This preparation is referred to as "formulation V".
  • Formulation W As a solution containing tetraconazole, Salvatore (registered trademark) ME (a solution containing 11.6 parts by weight of tetraconazole) manufactured by Arista Life Science Co., Ltd. was prepared. This preparation is referred to as "formulation W”.
  • Formulation X 50 parts by weight of flutoriahole (manufactured by Sigma) was dissolved in 950 parts by weight of dimethyl sulfoxide (manufactured by Tokyo Kasei Co., Ltd.). This preparation is referred to as "formulation X”.
  • Formulation Y 10 parts by weight of acibenzolar-S-methyl (manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in 990 parts by weight of dimethyl sulfoxide (manufactured by Tokyo Kasei Kogyo Co., Ltd.). This preparation is referred to as "formulation Y”.
  • Example 1 The above preparation E (pyraclostrobin 68000 ppm, boscalid 136000 ppm) and preparation A (nitrophenol compound 18000 ppm) were mixed to prepare preparation E + A of the composition of the present invention.
  • Formulation E was formulated as formulation F, formulation G, formulation H, formulation I, formulation J, formulation K, formulation L, formulation M, formulation N, formulation O, formulation P, formulation Q, formulation R, described in Tables 1-6.
  • Formulation G + A, Formulation H + A, Formulation I + A, Formulation J + A, Formulation K + A, Formulation L + A, Formulation M + A, Formulation N + A, Formulation O + A, Formulation P + A, Formulation Q + A, Formulation R + A, Formulation S + A, Formulation T + A, Formulation U + A, Formulation V + A, Formulation W + A , Formulation X + A, and formulation Y + A were prepared respectively.
  • Test Example 1 Efficacy Test Against Tomato Phytophthoma
  • the top 3 to 5 leaves of tomato (variety: large-sized Fukuju) grown to about 15 leaf stages were cut 5 cm from the tip and used for the test.
  • the drug was treated by immersing the cut leaves in a drug solution. After the treatment, it was allowed to stand on a plain agar medium with the back of the leaf up and air-dried.
  • a spore suspension of Phytophthora infestans was prepared with a pH 7.0 phosphate buffer to a density of 1 ⁇ 10 5 .
  • One hour after preparation, the spore suspension was sprinkled onto the leaves.
  • Three test zones were established per test zone.
  • the control was grown for 7 days under the conditions of noon: 15 ° C., night 12 ° C., illumination 12 hours. After that, the effect of each drug was evaluated by the affected area.
  • the result is Table 1.
  • the expected effectiveness (E) of the microbicidal composition of the present invention was calculated from the Colby's equation (Weeds, 15, 20-22 (1967)) to obtain the calculated effectiveness (%) .
  • E x + y-(x ⁇ y / 100)
  • E is the percentage of the expected efficacy when using the nitrophenol compound and the bactericidal compound at the respective concentrations p and q.
  • x represents the degree of effectiveness when a nitrophenol compound is used at a concentration p
  • y represents the degree of effectiveness when a bactericidal compound is used at a concentration q.
  • Test Example 2 Efficacy Test against Cucumber Powdery Mildew
  • a 7 cm pot was filled with a culture soil (trade name: Aina No. 1, manufactured by Katakura Coop Aggri Co., Ltd.), and a cucumber was sowed. When the third leaf was developed, a strain with moderate growth was selected and used for the test. After dilution of the drug, 4 ml per share was evenly sprayed by sprayer and allowed to air dry thoroughly.
  • a spore suspension of cucumber powdery mildew (Podosphaera xanthii or Sphaerotheca fuliginea) was prepared with a phosphate buffer of pH 7.0 to a density of 1 ⁇ 10 5 .
  • the spore suspension was sprayed on the surface of the strain evenly with a sprayer. Three test zones were established per test zone. Day: After managing for 7 days in a house at 25 ° C. and at 20 ° C. at night, the effects of each drug were evaluated by the area of disease onset. The results are shown in Table 3.
  • the synergistic bactericide composition (Example 19) of the present invention was found to have a synergetic effect, with the numerical value (measured value) of the control rate (%) being larger than the theoretical value.
  • the control effect on agricultural and horticultural pathogens is improved as compared to the existing bactericidal agent alone.
  • Test Example 3 Efficacy test against cucumber powdery mildew A culture medium (trade name: Aina No. 1, manufactured by Katakura Coop Aggri Co., Ltd.) was packed in a 7 cm pot and the cucumber was sowed. When the third leaf was developed, a strain with moderate growth was selected and used for the test.
  • the agents shown in Table 4 below were dissolved in a 10% by weight aqueous solution of Tween (registered trademark) 20 (the aqueous solution used pure water), and then 4 ml per strain was evenly sprayed by a sprayer and air-dried sufficiently.
  • a spore suspension of cucumber powdery mildew (Podosphaera xanthii) was prepared with a pH 7.0 phosphate buffer to a density of 1 ⁇ 10 5 .
  • the spore suspension was sprayed on the surface of the strain evenly with a sprayer. Three test zones were established per test zone. Day: After managing for 7 days in a house at 25 ° C. and at 20 ° C. at night, the effects of each drug were evaluated by the area of disease onset. The results are shown in Table 3.
  • the synergistic bactericide composition (Example 20) of the present invention was found to have a synergistic effect, with the numerical value (measured value) of the control rate (%) being larger than the theoretical value.
  • the control effect on agricultural and horticultural pathogens is improved as compared to the existing bactericidal agent alone.
  • Test Example 4 Efficacy test against cruciferous black spot bacterial disease Prepared at a predetermined concentration shown in the following Table 5 in about 3.5 leaf stage Chinese cabbage grown on a cell tray of 136 holes packed with Aina No. 1 soil The drug was sprayed using a spray gun (Olympos PB-408, 1.0 kgf / cm 2 ) at a spray rate of 6 ml / 8 strain. After spraying, it was allowed to stand in a room (16 L / 8 D) set at about 25 ° C. Two days after the spraying, the cells were spray-inoculated with a fungal solution of Brassicaceae black spot bacteria (Pseudomonas cannabina pv. Alisalensis).
  • the bacterial solution was prepared by diluting it to 1 ⁇ 10 8 cfu / ml with distilled water.
  • Chinese cabbage after inoculation was allowed to stand in a constant temperature and humidity room at 25 ° C. for 24 hours. It was then placed in an assay chamber at 25 ° C. About 7 days after inoculation, the incidence of the entire strain was investigated according to the following criteria to calculate the control value.
  • Test Example 5 Efficacy Test against Cucumber Powdery Mildew Cucumber (variety: Suzunari) grown to 1.2 leaf stage in a 7.5 cm pot packed with Aina No. 1 soil prepared to a predetermined concentration shown in Table 6 below The drug was sprayed at a spray water volume of 4.52 ml / strain using a rotary spray tower. Two days after spraying, it was left in a room (16 L / 8 D) at 25 ° C. Two days after spraying, 2 ml of the conidia suspension of cucumber powdery mildew (Podosphaera xanthi) was sprayed and inoculated.
  • the conidia suspension was prepared by immersing three cucumber leaves affected by powdery mildew on the whole of the first leaf in 100 ml of 0.01% Tween® 20 aqueous solution and shaking for 30 minutes. After inoculation, the cells were cultured in a house maintained at an average of 25 ° C. The control value was calculated by comparing the degree of onset of the entire strain with the untreated area 11 days after inoculation. The results are shown in Table 6.
  • the synergistic bactericidal composition (Examples 30 to 35) of the present invention was found to have a synergistic effect, with the numerical value (measured value) of the control rate (%) being larger than the theoretical value.
  • the control effect on agricultural and horticultural pathogens is improved as compared to the existing bactericidal agent alone.

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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)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention a pour objet de fournir une composition de fongicide présentant un effet de lutte amélioré contre les bactéries pathogènes dans les domaines agricole et horticole. Plus précisément, l'invention concerne (A) un composé nitrophénol, et (B) une composition de fongicide synergique comprenant un composé à activité fongicide. L'invention concerne également un procédé de lutte contre les bactéries pathogènes qui est caractéristique en ce que ladite composition de fongicide synergique traite l'habitat (les êtres humains étant exclus) des bactéries pathogènes dans les domaines agricole et horticole. L'invention concerne en outre un procédé de protection des plantes qui est caractéristique en ce que ladite composition de fongicide synergique traite une plante parasitée par des bactéries pathogènes dans les domaines agricole et horticole, ou les alentours de cette plante. L'invention concerne aussi un procédé de mise en œuvre du composé nitrophénol destiné à renforcer l'activité fongicide. Enfin, l'invention concerne un agent de renforcement d'activité fongicide comprenant le composé nitrophénol.
PCT/JP2018/047403 2017-12-24 2018-12-23 Composé nitrophénol, et composition de fongicide synergique comprenant un composé à activité fongicide WO2019124565A1 (fr)

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JP2019560607A JP7029186B2 (ja) 2017-12-24 2018-12-23 ニトロフェノール化合物及び殺菌活性化合物を含有する相乗的殺菌剤組成物

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CN101401573A (zh) * 2008-11-10 2009-04-08 云南省农业科学院农业环境资源研究所 一种预防姜瘟病的浸种剂及其制备方法和应用
CN105660731A (zh) * 2014-11-17 2016-06-15 武汉凌科达科技有限公司 一种水溶性农药的制备方法

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US3917850A (en) * 1973-06-05 1975-11-04 Wave Energy Systems Biocidal synergistic compositions for surface and space disinfection
WO2004013286A2 (fr) 2002-08-01 2004-02-12 Lta Resource Management Amplificateur du transport de proteines pour plantes transgeniques
CN103960264B (zh) * 2014-05-05 2015-07-01 河北双吉化工有限公司 一种含有吡唑醚菌酯、代森锰锌和复硝酚钠的杀菌组合物
CN104628481B (zh) 2015-02-10 2017-04-19 贵州三福生物科技有限公司 一种防除猕猴桃溃疡病的肥药组合剂及其制备方法
JP2016199527A (ja) 2015-04-14 2016-12-01 アグロカネショウ株式会社 有害生物防除剤組成物
CN106489956A (zh) * 2015-09-07 2017-03-15 四川利尔作物科学有限公司 农药组合物及其应用
JP2017100982A (ja) 2015-12-01 2017-06-08 日本農薬株式会社 農園芸用殺虫殺ダニ剤組成物及びその使用方法
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JPS63107904A (ja) * 1986-06-28 1988-05-12 Hokkai Sankyo Kk 植物病害防除剤
CN101401573A (zh) * 2008-11-10 2009-04-08 云南省农业科学院农业环境资源研究所 一种预防姜瘟病的浸种剂及其制备方法和应用
CN105660731A (zh) * 2014-11-17 2016-06-15 武汉凌科达科技有限公司 一种水溶性农药的制备方法

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KR20200104359A (ko) 2020-09-03

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