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WO2020179910A1 - Nouveau dérivé d'hydrazone et agents agricoles et horticoles l'utilisant comme principe actif - Google Patents

Nouveau dérivé d'hydrazone et agents agricoles et horticoles l'utilisant comme principe actif Download PDF

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Publication number
WO2020179910A1
WO2020179910A1 PCT/JP2020/009685 JP2020009685W WO2020179910A1 WO 2020179910 A1 WO2020179910 A1 WO 2020179910A1 JP 2020009685 W JP2020009685 W JP 2020009685W WO 2020179910 A1 WO2020179910 A1 WO 2020179910A1
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group
alkyl
alkoxy
formula
hydrogen atom
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Japanese (ja)
Inventor
秀一 薄井
恒一 荒木
祥 森下
福地　俊樹
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Agro Kanesho Co Ltd
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Agro Kanesho Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06—Coating or dressing seed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/08—Immunising seed
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/84—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 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/16—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/12—Oxygen or sulfur atoms

Definitions

  • the present invention relates to a novel hydrazone derivative and an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent or a nematode control agent, and a method of using the same.
  • Patent Document 1 describes that semicarbazone derivatives are useful as agricultural insecticides.
  • Patent Document 1 discloses a semicarbazone compound but does not disclose a hydrazone compound as in the present invention.
  • the compound described in Patent Document 1 does not describe any effect on nematodes.
  • the following compounds have been disclosed as analogs of the compounds of the present invention (eg, Patent Documents 2 to 4). However, each of these compounds disclosed in Patent Documents 2 to 4 differs in chemical structure from the compound of the present invention.
  • the present inventors have found that the hydrazone derivative represented by the following formula (1), which is a novel compound not described in the literature, is an agricultural and horticultural drug, particularly an agricultural and horticultural pest.
  • the present invention has been completed by finding it useful as a control agent or a nematode control agent. That is, the present invention has the following equation (1).
  • R 1 represents a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy C 1-6 alkyl group or an optionally substituted benzyl group.
  • R 2 indicates a formyl group, or R 1 and R 2 are combined, May form R 4 indicates OR 5 or NR 6 R 7
  • R 5 is C 1-6 alkyl group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C. 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or benzyl group.
  • R 6 represents a hydrogen atom or C 1-6 alkyl group
  • R 7 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkyl group, C 2-6 alkenyl group, C 2-6 haloalkenyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3-6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or benzyl
  • a group may be indicated, or R 6 and R 7 may be bonded to each other to form a saturated or unsaturated 4- to 7-membered ring with the nitrogen atom to which R 6 and R 7 are bonded.
  • R 3 indicates a C 1-6 alkyl group or phenyl group
  • X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C 2 -6 haloalkenyl group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 alkyl
  • a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or two Xs are present in place of hydrogen atoms on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring.
  • n indicates an integer from 1 to 5 Y 1 , Y 2 , Y 3 and Y 4 independently represent nitrogen atoms or CR groups, respectively.
  • R is independently hydrogen atom, C 1-6 alkyl, C 1-6 haloalkyl group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1- 6 Alkoxy group, C 1-6 alkyloxycarbonyl group, halogen atom, cyano group or nitro group.
  • hydrazone derivative represented by (1) or a salt thereof further relating to an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent or a nematode control agent, a method of using the same, and a method for producing the compound and the like. It is a thing.
  • the compound of the present invention exerts an excellent effect as an agricultural and horticultural agent, particularly as an agricultural and horticultural pest control agent or a nematode control agent. It is also effective against pests that parasitize pet animals such as dogs and cats, and livestock such as cows and sheep.
  • halogen atom means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom
  • C 1-6 alkyl group means, for example, a methyl group, an ethyl group, an n-propyl group or i. -Propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, n-hexyl group, isohexyl group, etc.
  • C 1-6 haloalkyl It represents an alkyl group having 1 to 6 carbon atoms in a chain or branched chain, and is a linear or branched chain substituted with one or more halogen atoms which may be the same or different from "C 1-6 haloalkyl".
  • C 3-6 cycloalkyl refers to a cyclic cycloalkyl group having 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Shown.
  • R 6 and R 7 can bond to each other and combine with the nitrogen atoms bonded to R 6 and R 7 to form a 4- to 7-membered ring, even if the ring is saturated. It may be unsaturated.
  • the saturated ring include an azacyclobutane ring, a pyrrolidine ring, a piperidine ring, a morpholine ring, a thiomorpholine ring, a hexamethyleneimine ring and the like
  • examples of the unsaturated ring include pyrazole, imidazole and 1,3,4-triazole. , 1,2,3-triazole, tetrazole and the like.
  • the saturated or unsaturated 5- or 6-membered ring may be a carbocycle or a heterocycle.
  • Examples of the C 1-6 haloalkyl group include a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, a bromodifluoromethyl group, a dichlorofluoromethyl group, a 1-fluoroethyl group, and 2 -Fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 2,2- Difluoroethyl group, 1-fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, heptafluoroisopropyl group, 4-fluor
  • Examples of the C 2-6 alkenyl group include a vinyl group, an allyl group, an isopropenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-pentenyl group and a 3-pentenyl group.
  • Examples of the C 2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group and 3,3-difluoro-2-allyl group.
  • Examples of the C 2-6 alkynyl group include an ethynyl group, a 2-propynyl group, a 1-methyl-2-propynyl group, a 1,1-dimethyl-2-propynyl group, a 1-butynyl group, a 2-butynyl group, and 3 -Butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 1-methyl-3-butynyl group, 1,1-dimethyl-2- It has 2 to 6 carbon atoms and has at least one triple bond at any position such as a butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc.
  • Examples include linear or branched alkynyl groups.
  • Examples of the C 2-6 haloalkynyl group include a fluoroethynyl group, a 4,4,4-trifluoro-2-butynyl group, a 5,5,5-trifluoro-3-pentynyl group, and a 1-methyl-3,3. Substituted with 1-9 halogen atoms having at least one triple bond at any position such as 3-trifluoro-2-butynyl group, 1-methyl-5,5,5-trifluoro-2-pentynyl group Examples thereof include a linear or branched alkynyl group having 2 to 6 carbon atoms.
  • the benzyl group which may be substituted may be, for example, substituted with a C 1-6 alkyl group, a halogen atom, a C 1-6 alkoxy group, a C 1-6 haloalkyl group, or a C 1-6 haloalkoxy group.
  • a good benzyl group is mentioned.
  • Examples of the C 1-6 alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropyloxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group. , N-Hexyloxy group and other linear or branched alkoxy groups having 1 to 6 carbon atoms can be mentioned.
  • Examples of the C 1-6 haloalkoxy group include fluoromethoxy group, dichloromethoxy group, trichloromethoxy group, difluoromethoxy group, trifluoromethoxy group, chlorodifluoromethoxy group, bromodifluoromethoxy group, dichlorofluoromethoxy group, 1- Fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group, penta Fluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group and the like, preferably 1 to 9 Examples thereof include linear or branched alkoxy groups having 1 to 6 carbon atoms substituted with halogen atoms.
  • Examples of the C 3-6 halocycloalkyl group include 1-fluorocyclopropyl, 2-fluorocyclopropyl, 2,2-difluorocyclopropyl, 2,2,3,3-tetrafluorocyclopropyl and 1-chlorocyclo.
  • Cycloalkyl C 1-6 alkyl groups include, for example, cyclopropylmethyl, 2-cyclopropylethyl, 3-cyclopropylpropyl, 4-cyclopropylbutyl, 5-cyclopropylpentyl, 6-cyclopropylhexyl. And groups such as cyclobutylmethyl and cyclopentylmethyl.
  • Examples of the C 1-6 alkoxycarbonyl group include groups such as methoxycarbonyl, ethoxycarbonyl, n-propylcarbonyl, n-butylcarbonyl, n-pentylcarbonyl, n-hexylcarbonyl and i-propylcarbonyl groups.
  • Examples of the C 1-6 alkoxy C 1-6 alkyl group include groups such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group and 3-methoxypropyl group.
  • Examples of the hydroxy C 1-6 alkyl group include groups such as hydroxymethyl group, 2-hydroxyethyl group, 2-hydroxypropyl group, 3-hydroxypropyl group and 3-hydroxy-2,2-dimethylpropyl group.
  • Examples of the C 1-6 alkylthio group include a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, a cyclopropylthio group, an n-butylthio group, an s-butylthio group, a t-butylthio group and an n-pentylthio group.
  • N-Hexylthio group and the like a linear or branched alkylthio group having 1 to 6 carbon atoms can be mentioned.
  • Examples of the C 1-6 alkylsulfinyl group include methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, cyclopropylsulfinyl group, n-butylsulfinyl group, s-butylsulfinyl group and t-butyl.
  • Examples thereof include linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms such as a sulfinyl group, an n-pentylsulfinyl group, and an n-hexylsulfinyl group.
  • Examples of the C 1-6 alkylsulfonyl group include a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, cyclopropylsulfonyl group, n-butylsulfonyl group, s-butylsulfonyl group, t-butyl group.
  • Examples thereof include a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms such as a sulfonyl group, an n-pentylsulfonyl group, and an n-hexylsulfonyl group.
  • Examples of the salt of the hydrazone derivative represented by the formula (1) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, and acetates, fumarates, maleates and oxalic acids. Examples thereof include salts, methanesulfonate, benzenesulfonate, p-toluenesulfonate, and other organic acid salts.
  • the compounds described herein may contain one or more asymmetric centers in their structural formulas, and may contain two or more optical isomers and diastereomers. It also includes all optical isomers and mixtures containing them in arbitrary proportions.
  • the compounds described in the present specification may have two or more kinds of geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond in the structural formula, but the present invention Includes all geometric isomers and mixtures containing them in arbitrary proportions.
  • the wavy line may be any of two or more geometric isomers derived from a carbon-carbon double bond or a carbon-nitrogen double bond. Means inclusion.
  • Y 2 shows CR.
  • R represents a C 1-6 haloalkyl group.
  • R 3 represents a methyl group, an ethyl group or an isopropyl group.
  • Y 2 represents CR, R represents a C 1-6 haloalkyl group, and R 3 represents a methyl group, an ethyl group or an isopropyl group. preferable.
  • R 3 represents a C 1-6 alkyl group or phenyl group
  • X may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, C 3-6 cycloalkyl group, C 2-6 alkoxy group, C 2-6 alkynyl group, C 2 -6 haloalkenyl group, C 2-6 haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 1-6 alkylthio group, C 3-6 halocycloalkyl group, C 1-6 alkyl
  • a coxycarbonyl group, formyl group, halogen atom, cyano group or nitro group is indicated, or two Xs are present in place of hydrogen atoms on two adjacent carbon atoms, the above two X may be combined with the carbon atoms to which each is bonded to form a saturated or unsaturated 5- or 6-membered ring
  • n indicates an integer from 1 to 5 Y 1 , Y 2 , Y 3 and Y 4 independently represent nitrogen atoms or CR groups, respectively.
  • R is independently hydrogen atom, C 1-6 alkyl, C 1-6 haloalkyl group, C 1-6 alkylthio group, C 1-6 alkylsulfinyl group, C 1-6 alkylsulfonyl group, C 1- Shows 6 alkoxy groups, C 1-6 alkyloxycarbonyl groups, halogen atoms, cyano groups or nitro groups, Hal represents a halogen atom.
  • the ketone derivative represented by the formula (3) is a base of the ⁇ -halogen ketone compound represented by the formula (14) and the azole compound of the formula (15). It can be produced by reacting in an inert solvent in the presence or absence.
  • solvents can be widely used as long as they are inert to the reaction.
  • a solvent include aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, xylene, methylene chloride, 1,2- Halogenated hydrocarbon solvents such as dichloroethane and chloroform, ether solvents such as diethyl ether, tetrahydrofuran and 1,4-dioxane, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, Examples thereof include amide solvents such as N-dimethylformamide, nitrile solvents such as acetonitrile and propionitrile,
  • one of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
  • known inorganic bases and organic bases can be used.
  • the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and sodium bicarbonate, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkali metal hydrogen such as sodium hydride and potassium hydride.
  • Examples of the organic base include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide, amines such as triethylamine and pyridine. These bases may be used alone or in combination of two or more.
  • Such a base can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the ketone compound represented by the formula (14).
  • the ratio of the ⁇ -halogen ketone compound represented by the formula (14) to the azole compound represented by the formula (15) is 1 to 1.2 mol of the compound (15) to the compound (14). It is more preferable to do so.
  • the reaction can usually be carried out in the range from ⁇ 78 ° C. to the boiling point temperature of the solvent used, and it is preferable to carry out the reaction at room temperature to 100 ° C.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.5 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • a commonly used isolation means for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • Reaction formula 2 [In the formula, R 1 represents a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy C 1-6 alkyl group or an optionally substituted benzyl group, X, Y 1 , Y 2 , Y 3 , Y 4 , R 3 and n are as defined in the above equation (3). ]
  • the hydrazone derivative represented by the formula (2) is a ketone compound represented by the formula (3) and a hydrazine compound represented by the formula (13) in the presence of an acid or. It can be produced by reacting in an inert solvent in the absence.
  • a widely known solvent can be widely used as long as it is inert to the reaction.
  • examples of such a solvent include alcohols such as methanol, ethanol, n-propanol and iso-propanol, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, benzene, chlorobenzene, toluene and xylene.
  • Aromatic hydrocarbon solvents such as methylene chloride, 1,2-dichloroethane, halogenated hydrocarbon solvents such as chloroform, ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl acetate, ethyl acetate and the like.
  • ether solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, methyl acetate, ethyl acetate and the like.
  • ester-based solvents such as N, N-dimethylformamide
  • solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, and acetonitrile.
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
  • inorganic acids and organic acids can be used as the acid used in the reaction between the compound of the formula (3) and the compound of the formula (13).
  • inorganic acid include hydrogen chloride, hydrogen bromide, sulfuric acid, nitric acid and the like.
  • organic acid include acetic acid, propionic acid, citric acid, methanesulfonic acid, ethanesulfonic acid, p-toluenesulfonic acid and the like. These acids may be used alone or in combination of two or more. Such an acid can be used in an amount usually 0.001 to 2 equivalents, preferably 0.01 to 1 equivalent, relative to the ketone compound represented by the formula (3).
  • the ratio of the ketone derivative of the formula (3) to the hydrazine compound represented by the formula (13) can be appropriately selected from a wide range, but the latter is 1 to 10 with respect to 1 mol of the former. It is preferably used in an amount of at least mol, more preferably 2.0 to 5.0 mol.
  • the reaction is preferably carried out at 0 ° C. to the boiling point temperature of the solvent used, and more preferably from room temperature to heating under reflux.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the desired product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Further, it is also possible to use the product of interest in the next reaction step without isolating it from the reaction system.
  • Reaction formula 3 [In the formula, R 8 represents a C 1-6 alkyl group, and X, Y 1 , Y 2 , Y 3 , Y 4 , R 1 , R 3 and n are defined by the above formulas (2) and (3). On the street. ]
  • the hydrazone derivative represented by the formula (4) is a hydrazone derivative represented by the formula (2) and formic acid and / or a formic acid derivative represented by the formula (5). Can be produced by the formylation reaction of.
  • solvents used in the formylation reaction of the hydrazone compound represented by the formula (2) can be used as long as they are inert to the reaction.
  • examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane, and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene, and xylene, methylene chloride, 1,2-.
  • Halogenated hydrocarbon solvents such as dichloroethane and chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and the like, acetic acid can be mentioned.
  • alcohol solvents such as methanol and ethanol
  • ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate
  • ketone solvents such as acetone and methyl ethyl ketone
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
  • Examples of the formylating agent used in the formylation reaction of the hydrazone compound represented by the formula (2) include formic acid, methyl formate, ethyl formate and the like. Such a formylating agent can be used usually in an amount of 1 to 100 equivalents, preferably 1 to 10 equivalents, relative to the hydrazone derivative represented by the formula (2).
  • the reaction can be carried out usually in the range of ⁇ 78° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at 0° C. to the boiling temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • Reaction equation 4 [In the formula, R 8 represents a C 1-6 alkyl group, and X, Y 1 , Y 2 , Y 3 , Y 4 , R 1 , R 3 , R 4 and n are the above formulas (1) to (3). As defined in. ] Specific examples of the reaction formula 4 include those represented by the reaction formulas 5 and 7 described below.
  • Reaction equation 5 [In the formula, R 1 represents a hydrogen atom, R 8 represents a C 1-6 alkyl group, and X, Y 1 , Y 2 , Y 3 , Y 4 , R 3 and n are as defined above. ]
  • the hydrazone derivative represented by the formula (9) can be produced by reacting the hydrazone derivative represented by the formula (2) with the orthoformate ester (16).
  • a widely known solvent is widely used as long as it is inert to the reaction. can do.
  • examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane, and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene, and xylene, methylene chloride, 1,2-.
  • Halogenated hydrocarbon solvents such as dichloroethane and chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and the like, acetic acid can be mentioned.
  • alcohol solvents such as methanol and ethanol
  • ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate
  • ketone solvents such as acetone and methyl ethyl ketone
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
  • Examples of the orthoformate ester (16) used in the iminization reaction of the hydrazone compound represented by the formula (2) include methyl orthoformate, ethyl orthoformate, propyl orthoformate, butyl orthoformate and the like. Such an orthoformate ester (16) can be used in an amount usually 1 to 20 equivalents, preferably 2 to 10 equivalents, relative to the hydrazone derivative represented by the formula (2).
  • the reaction can be carried out usually in the range of ⁇ 78° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at 0° C. to the boiling temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • R 6 represents a hydrogen atom or C 1-6 alkyl group
  • R 7 is a hydrogen atom, C 1-6 alkyl group, C 1-6 alkoxy group, C 1-6 haloalkyl group, C 2- 6 Alkyl group, C 2-6 haloalkyl group, C 2-6 alkynyl group, C 2-6 haloalkynyl group, hydroxy C 1-6 alkyl group, C 1-6 alkoxy C 1-6 alkyl group, C 3- 6 cycloalkyl group, C 3-6 cycloalkyl C 1-6 alkyl group or benzyl group, or R 6 and R 7 are bonded to each other with the nitrogen atom to which R 6 and R 7 are bonded.
  • the hydrazone derivative represented by the formula (8) is produced by reacting the hydrazone derivative represented by the formula (9) with the amine derivative represented by the formula (10). can do.
  • solvents used in the amination reaction of the hydrazone compound represented by the above formula (9) widely known solvents can be used as long as they are inert to the reaction.
  • examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane, and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene, and xylene, methylene chloride, 1,2-.
  • Halogenated hydrocarbon solvents such as dichloroethane and chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and the like, acetic acid can be mentioned.
  • alcohol solvents such as methanol and ethanol
  • ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate
  • ketone solvents such as acetone and methyl ethyl ketone
  • the amine derivative (10) can be used usually in an amount of 1 to 5 equivalents, preferably 1 to 2.5 equivalents, relative to the hydrazone derivative represented by the formula (9).
  • the reaction can be carried out usually in the range of ⁇ 78° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at 0° C. to the boiling temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • a commonly used isolation means for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • Reaction equation 7 [In the equation, R 1 represents a hydrogen atom, and X, Y 1 , Y 2 , Y 3 , Y 4 , R 3 , R 6 , R 7 , R 8 and n are as defined above. ]
  • the hydrazone derivative represented by the formula (8) can be produced by reacting the hydrazone derivative represented by the formula (2) with the acetal derivative (17).
  • solvents used in the reaction between the hydrazone compound represented by the formula (2) and the acetal derivative represented by the formula (17) widely known solvents are used as long as they are inert to the reaction. be able to.
  • examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane, and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene, and xylene, methylene chloride, 1,2-.
  • Halogenated hydrocarbon solvents such as dichloroethane and chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and the like, acetic acid can be mentioned.
  • alcohol solvents such as methanol and ethanol
  • ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate
  • ketone solvents such as acetone and methyl ethyl ketone
  • acetal derivative (17) used in the iminoization reaction of the hydrazone compound represented by the formula (2) include N,N-dimethylformamide dimethylacetal.
  • the acetal derivative (17) can be used in an amount of usually 1 to 10 equivalents, preferably 1 to 5 equivalents, relative to the hydrazone derivative represented by the above formula (2).
  • the reaction can be carried out usually in the range of ⁇ 78° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at 0° C. to the boiling temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • Reaction equation 8 [In the formula, L indicates a leaving group such as a halogen atom and CH 3 OSO 3- , and X, Y 1 , Y 2 , Y 3 , Y 4 , R 1 , R 3 and n are the above formula (2). And as defined in (3). ]
  • the hydrazone derivative represented by the formula (4) is a hydrazone derivative represented by the formula (11) and an alkylating agent represented by the formula (12). It can be produced by reacting in an inert solvent in the presence or absence of a base.
  • a widely known solvent can be widely used as long as it is inert to the reaction.
  • examples of such a solvent include an aliphatic or alicyclic hydrocarbon solvent such as hexane, cyclohexane, and heptane, an aromatic hydrocarbon solvent such as benzene, chlorobenzene, toluene, and xylene, methylene chloride, 1,2-.
  • Halogenated hydrocarbon solvents such as dichloroethane and chloroform, alcohol solvents such as methanol and ethanol, ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, N, N -Amid-based solvents such as dimethylformamide, nitrile-based solvents such as acetonitrile and propionitrile, aprotonic polar solvents such as N-methylpyrrolidone and N, N'-dimethylimidazolinone, and the like, acetic acid can be mentioned.
  • alcohol solvents such as methanol and ethanol
  • ester solvents such as methyl formate, ethyl formate, methyl acetate and ethyl acetate
  • ketone solvents such as acetone and methyl ethyl ketone
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required.
  • Examples of the alkylating agent (12) used in the alkylation reaction of the hydrazone compound represented by the formula (11) include methyl iodide, ethyl iodide, dimethyl sulfate and the like.
  • Such an alkylating agent can be used in an amount usually 1 to 10 equivalents, preferably 1 to 2 equivalents, relative to the hydrazone derivative represented by the above formula (11).
  • the reaction can be carried out usually in the range of ⁇ 78° C. to the boiling temperature of the solvent used, and the reaction is preferably carried out at 0° C. to the boiling temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unconditionally stated, but the reaction is usually completed in about 0.1 to 24 hours.
  • the target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by a commonly used isolation means, for example, an organic solvent extraction method, a chromatography method, a recrystallization method, a distillation method or the like. Further, it can be purified by conventional purification means.
  • Typical compounds of the ketone derivatives to be used are illustrated in Table 3, but the present invention is not limited thereto.
  • Tables 1 to 3 the physical properties or melting point (° C.) are shown, "n-” means normal, “s-” means secondary, “t-” means tertiary, and "i-”.
  • the compounds of the present invention can be used in agriculture, indoors or in forests for the prevention and control of organisms that are harmful to livestock or in various situations such as hygiene. Specific usage situations, target pests, and usage methods are shown below, but the content of the present invention is not limited thereto.
  • the compound of the present invention represented by the above formula (1) is an agricultural crop, for example, an edible crop (wheat such as rice, barley, wheat, rye, oat, corn, horse bell ⁇ , sweet potato, satoimo, soybean, red bean, sora bean, Beans such as beans, green beans, peanuts, etc.), vegetables (cabbage, white vegetables, radish, buds, broccoli, potash flowers, komatsuna, etc., Abrana crops, pumpkin, cucumber, squid, makuwauri, melon, etc.
  • an edible crop such as rice, barley, wheat, rye, oat, corn, horse bell ⁇ , sweet potato, satoimo, soybean, red bean, sora bean, Beans such as beans, green beans, peanuts, etc.
  • vegetables cabbage, white vegetables, radish, buds, broccoli, potash flowers, komatsuna, etc.
  • Abrana crops pumpkin, cucumber, squid, makuw
  • Lepidoptera of the phylum Arthropod for example, Cossidae (Helicoverpa armigera), Heliothis spp., Kabrayaga (Agrotis segetum), Tamanagin uwaba (Autographa nigrisigna), Irakusagi uwaba (Tricho) ), Spodoptera exigua, Spodoptera exigua, Spodoptera litura, etc., Plutella xylostella, etc.
  • Iraga (Monema flavecens), Hirohelia oila (Parasa lepida), Himekuroiraga (Scopelodes con) Tracus, etc., Crambid snout moth (Chilo suppressalis), Sankameiga (Scirpophaga incertulas), Kobunomeiga (Cnaphalocrocis medinalis), Himadara nomeiga (Hellulla undalis), Momogomadarameiga (Conogethes punctiferlis), Watahelis Parapediasia teterrella, etc., Tosakaftomeiga (Locastra muscosalis), etc.
  • Coleoptera for example, the weevil weevil (Anomala cuprea), the leaf beetle (Popillia japonica), the leaf beetle (Oxycetonia jucunda), the leaf beetle (Anomala geniculata), etc., the leaf beetle (Anomala geniculata), etc.
  • Beetle beetle Marekbiku beetle (Melanotus fortnumi) etc., ladybug family Nijuyahoushi tentou (Epilachna vigintioctopunctata) etc., long-horned beetle beetle beetle (Anoplophora malaca), grape tiger beetle dermatus (Anoplophora) malpyca humorus (Xylot).
  • Aulacophora femoralis Rootworm species (Diabrotica spp.), Phyllotreta striolata, Chaenot beetle (Cassida nebulosa), Phaeedon brassicaeino (Oulema oryzae la), Epilachan (Eulema oryzae), Epilum (Eulema oryzae la), Epilum (Eulema oryzae), Epilach (Epilema) orepil (Eulema oryzae) ), etc., Rhynchites heroes of the family Weevilidae, etc., ant weevil of the family Weevil Weevil (Cylas formicarius), etc., Curculio suri (Curculious siwakitamen) of the weevil family, Lissorophilus (Lysorophilus), Lissorhopt grandis), weevil (Sphenophrus venatus vestitus), and other adults
  • Hemiptera stink bugs Heteroptera
  • stink bugs Eurydema rugosum
  • stink bugs Eysarcoris lewisi
  • stink bugs Eysarcoris parvus
  • stink bugs Eysarcoris parvus
  • stink bugs Eysarcoris parvus
  • stink bugs Eysarcoris parvus
  • Stink bug Plautia stali
  • stink bug Halymorpha mista
  • stink bug Urochela luteovoria
  • stink bug family stink bug Togo hemipterus) stink bug (Togo hemipterus) stink bug (Togo hemipterus) stink bug (Togo hemipterus) stink bug , Stink bug (Cletus punctiger), stink bug (Leptocorisa chinansis), stink bug (Dysdeercus cingulatus), stink bug (Dysdeercus cingulatus), stink bug (Stephanitis stink bug), stink bug
  • Hemiptera aphids such as the semi-family Platypleura kaempferi, the aphid family Arboridia apicalis, Chanomidorihimeyokobai (Empoasca onukii), cinmagro , White-necked leafhoppers (Nephotettix virescens), etc., planthoppers (Laodelphax striatellus), brown planthoppers (Nilaparvata lugens), etc.
  • Homoptera such as the semi-family Platypleura kaempferi, the aphid family Arboridia apicalis, Chanomidorihimeyokobai (Empoasca onukii), cinmagro , White-necked leafhoppers (Nephotettix virescens), etc., planthoppers (Laodelphax striatellus), brown planthoppers (Nilaparvata lugens), etc.
  • Thrips Thrips (Thysanoptera), for example, Thrips thrips (Thirs) tabis, Thrips, tabis, Thrips, tabi, Thrips thrips, Thrips, tabis, Thrips thrips, Thrips, and Thrips, Tabis, Thrips, Thrips, and Thrips.
  • Thrips palmi Karny (Frankliniella occidentalis), Thrips palmi Karny (Heliothrips haemorrhoidalis), etc., Thrips palmi Karny (Ponticulothrips diospyrosi), Thrips palmi Karny (Ponticulothrips diospyrosi), Thrips palmi Karny (Haplothrips)
  • Hymenoptera for example, Tenthredinidae (Athalia rosae ruficornis), Churange bee (Arge pagana), etc., Formica japonica (Arge mali), etc.
  • Adults such as the leaf-cutting bees (Megachile nipponica nipponica), Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Fire ant (Solenopsis richteri, S. invicta, S. geminata), etc.
  • Drosophila suzukii such as Limeomyza trifolii, tomato leaf fly (Liriomyza sativae), leaf fly (Chromatomyia horticola), rice leaf fly (Agromyza oririza), eggplant leafhopper (Agromyza oryzae), eggplant leaflet (Agromyza oryzae) Adults, larvae and eggs such as leafminer (Delia platura) and leafminer fly (Delia antiqua);
  • Orthoptera for example, Locusta migratoria in the grasshopper family, Ruspolia lineosa in the grasshopper family, etc.
  • Etc. adults such as Oxya yezoensis of the grasshopper family, larvae and eggs;
  • Collembola of the phyla Insecta for example, adults such as Sminthurus viridis of the genus Maltobidae, nymphs of the genus Matsumotoi (Onychiurus matsumotoi), larvae and eggs; Adults, larvae and eggs of the Collembola (Isopada), such as the pill bug (Armadillidium vulgare) of the pill bug family; Mites of the arthropod spider (Acari), for example, Polyphagotarsonemus latus of the dust mite family, Pytonemus pallidus, etc., and the genus Mite mite (Penthaleus major) of the spider mite family, etc.
  • Minamihime spider mite (Brevipalpus phoenicis), spider mite (Panonychus citri), apple spider mite (Panonychus ulmi), Nami spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Oligonychus ununguis), Kikubira spider mite (Bryobia eharai), Miyakeake spider mite (Eotetranychus kankitus), Clover spider mite (Bryobia praetiosa), apple sabi mite (Aculus Schlechtendali), mites ), Fake mite (Eriophyes chibaensis), Tulip mite (Aceria tulipae), Grape hamogri mite (Colomerus vitis), Peach mite (Aculus fockeui), Chanosabi mite (Calacarus carinatus), etc.
  • Primitive string tongues of the molluscs Gastropods for example, Pulmonata (Plumonata), such as Pomacea canaliculata, Giant African Snail (Achatina fulica), Giant African Snail Namekuji (Meghimatium bilineatum), Niwakouranamekuji (Milax gagates), Kouranamekuji family Chakouranamekuji (Lehmannina valentiana), Onajimaimai family Uskawamaimai (Acusta despecta sieboldiana), etc.
  • Pulmonata Pulmonata
  • Pulmonata Pulmonata
  • Giant African Snail Achatina fulica
  • Giant African Snail Namekuji Meghimatium bilineatum
  • Niwakouranamekuji Milax gagates
  • Kouranamekuji family Chakouranamekuji Lehmannina valentiana
  • Tylenchida of the family Secernentea for example, Ditylenchus destructor of the family Anguina, Tylenchorhynchus claytoni of the family Tylenchorhynchus, etc., Pratylenchus pen of the family Platylenchus ), Minami Negusa Cereae (Pratylenchus coffeae), etc., Hopilolymaceae Namila Centenum (Helicotylenchus dihystera), etc., Heterodera family potato cyst nematodes (Globodera rostochiensis), etc.
  • Nematodes (Criconema jaejuense), etc., Strawberry nematodes (Nothotylenchus acris), etc., Aphelecchoides fragarriae, etc .; Pratylenchus rosacea, for example .), Yumihari nematode (Trichodorus sp.), Etc. of the family Trichodolus family; Fungi and bacteria such as the phylum Eumycota, the phylum Dictyostelium (Myxomycota), the phylum Bacteriomycota, the phylum Actinomycota (Actinomycota).
  • diseases to which the compound of the present invention represented by the above formula (1) can be applied include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and blight (Rhizoctonia solani). ), Inner browning disease (Pantoea ananatis), Brown streak disease (Acidovorax avene subsp. Avenae), Leaf sheath browning disease (Pseudomonas fuscovaginae), White leaf blight (Xanthomonas oryzae pv.
  • Bacterial wilt disease Bacterial wilt disease (Burkholderia plantari) Udonko disease (Erysiphe graminis), Fusarium head blight (Gibberella zeae), Fusarium head blight (Puccinia striiformis, P. graminis, P. recondita, P. hordei), Snow rot (Typhula sp., Micronectriella nivalis) , Naked black spike disease (Ustilago tritici, U.
  • pirina black spot disease (Alternaria kikuchiana), gymnosporangium haraeanum, monilinia fructigena, etc .; thigh monilinia fructicola, cladosporium carpophilum, phomopsis rot.
  • Phomopsis sp. Perforated bacterial disease (Brenneria nigrifluens), etc .; Grape black scab (Elsinoe ampelina), late rot (Colletotrichum acutatum), udonko disease (Uncinula necator), rust disease (Phakopsora ampelopsidis), black lot disease (Phakopsora ampelopsidis) Guignardia bidwellii, Plasmopara viticola, Monilinia fructigena, Cladosporium viticolum, Botrytis cinerea, Agrobacterium vitis, etc.; Gloeosporium kaki, deciduous disease (Cercospora kaki, Mycoshaerella nawae), etc .; Colletotrichum lagenarium, Sphaerotheca fuliginea, Oidiopsis taurica, vine blight (Dipopsi taurica), vine blight (Glo
  • Cucurbitae hair root disease (Agrobacterium rhizogens), cancerous disease (Streptomyces sp.), Etc.; Fruit stain bacterial disease (Acidovorax avenae pv. Citrulli), etc .; Bacterial wilt disease (Ralstonia solanacearum), etc. of Xanthomonas camps; Tomato ring pattern disease (Alternaria solani), leaf mold disease (Cladosporium fullvum), epidemic (Phytophthora infestans) ), Canker disease (Clavibacter michiganense subsp.
  • Brown spot disease (Cercospora arachidicola), etc .; Powdery mildew (Erysiphe pisi), etc .; Summer epidemic of potato (Alternaria solani), Epidemic (Phytophthora infestans), Leaf rot fungus (Rhizoctonia solani), etc.; Strawberry powdery mildew Sphaerotheca humuli, etc .; Tea net blast (Exobasidium reticulatum), White star disease (Elsinoe leucospila), Red burning disease (Pseudomonas syringae pv. Theae), Powdery mildew (Xanthomonas campestris pv. Theicola), etc.
  • the compound of the present invention represented by the above formula (1) acts indoors in a building including a general house, and damages or rots wood and its processed products such as wooden furniture, stored foods, clothing, books, etc. It can also be used to control arthropods and fungi that damage our lives.
  • Specific pests include the following.
  • Termites of the phylum Arthropoda for example, the termites (Coptotermes formosanus), Reticulitermes speratus, and other termites of the genus Reticulitermes (Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), American termites (Incisitermes minor), termites (Odontotermes formosanus), termites (Hodotermopsis jzponica), adult termites (Cryptotermes domesticus) larvae, Cryptotermes domesticus.
  • Tribolium castaneum, Tribolium confusum, etc. such as Oryzaephilus surinamensis, which is a member of the family Astragalus spp. (Stegobium paniceum) etc., Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus etc., etc.
  • Lepidoptera for example, Cudra cautella, Ephestia kuehniella, Plodia interpunctella, etc.; Sitotroga cerealella, etc.; Adults such as translucens) and carp (Tineola bisselliella), larvae and eggs; adults, larvae and eggs of Chaptera, such as, for example, Lepinotus reticulatus of the family Kochaate, Liposcelis bostrychophilus, etc.
  • cockroaches for example Blattella germanica of the cockroach family, Periplaneta fuliginosa, cockroaches of the cockroach family, Periplaneta japonica; Hymenoptera, for example, the house ant (Monomorium) pharaoni), adult larvae and eggs such as black ants (Monomorium nipponense);
  • Thysanura such as Ctenolepisma villosa and Lepisma saccharina of the family Lepismatidae
  • Adults, larvae and eggs of the order Flies such as Drosophila melangogaster of the Drosophila family, Piophila casei of the Piophila family, etc.
  • Adults, larvae and eggs of the order Arachnids of the phylum Arachnid such as Tyrophagus putrescentiae of the family Acaridae, Lardoglyphus konoi, and Carpoglyphus lactis of the family Carpoglyphus lactis
  • Tyromyces palustris Coriolus versicolor, etc.
  • Microorganisms such as Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium ci
  • the compound of the present invention represented by the above formula (1) can also be used to control harmful organisms that damage or weaken trees in natural forests, planted forests and urban green spaces.
  • Specific pests include the following.
  • Arthropod phylum Insectidae for example, Sugidokuga (Calliteara argentata), Chadokuga (Euproctis pseudoconspersa), Himeshiromondokuga (Orygiafur approximans), Dokuga (Euproctis subflava), Maiga (Lymantria disp) Family Ochokareha (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Tsugakareha (Dendrolimus superans), etc., Meiga family Larix (Crytoblabes, loxiella), etc., Moth family Kabrayamaga (Agrotis), etc.
  • Hemiptera for example, Cinara todocola of the Aphididae family, Adelges japonicus of the Aphididae family, Diaspididae Sugimarukaigaramushi (Aspidiotus cryptomeriae), etc.
  • the compound of the present invention represented by the above formula (1) is internal to vertebrates, particularly domestic animals and pets such as cows, sheep, goats, horses, pigs, poultry, dogs, cats and fish, which are warm-blooded vertebrates. It can also be used to prevent, treat or control arthropods, nematodes, pets, streaks and protozoa that parasitize or externally.
  • the target animal species also include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, and avian pets such as ducks and pigeons and experimental animals. Specific pests include the following.
  • Flies of the phylum Arthropod such as Yamatoab (Tabanus rufidens), Akaushiab (Tabanus chrysurus), Blowfly (Musca bezzii), Psychodidae (Musca domestica), Psychodidae (Stomoxys calcitrans), etc.
  • Ceratopogonidae (Gasterophilus intestinalis), Ceratopogonidae (Hypoderma bovis), Psychodidae (Oestrus ovis), Blowfly (Aldrichina grahami), Ceratopogonidae (Ceratopogonidae) Etc., Botfly (Sepsis punctum), Psychodidae (Telmatoscopus albipunctatus), Blowfly (Psychoda alternata), Ceratopogonidae (Culex pipiens molestus), Ceratopogonidae (Culex piens molestus) , Sinahamadaraka (Anopheles sinensis), Kogata Akai Eka (Culex pipiens triaeniorhynchus summorosus), Hitosujishimaka (Ades albopictus), etc.
  • Lice for example, porcelain lice (Haematopinidae suis), cattle lice (Haematopinidae eurysternus), etc.
  • Adults, larvae and eggs such as (Menopon gallinae); Arthropod spider mites, such as the itch mite (Varroa jacobsoni), the itch mite (Haemaphysalis longicornis), the itch mite (Ixodes ovatus), the itch mite (Boophilus microplus), and the itch mite (Boophilus microplus).
  • testudinarium etc.
  • Ornithonyssus sylvialum etc.
  • Wakumo Dermatyssus gallinae
  • Itch mite Demodex phylloides
  • Itch mite Itch mite
  • Itch mite Stecoptes scabiei bovis
  • Adults, larvae and eggs such as (Knemidocoptes mutans), itch mite (Otodectes cynotis), bovine itch mite (Psoroptes communis), etc.
  • C. elegans C.
  • elegans for example, Bunostomum pheasum, Metastrongylus elongata, Metastrongylus elongata, Hairy nematode, Oesophagostomia, etc .
  • Roundworms For example, Ascaris suum, Ascaridia galliate, etc.; Flatworm phylum flukes, such as Schistosoma japonicum, liver tetsu, deer amphistomiasis, Paragonimus westermani, Japanese chicken egg fluke, etc.; Tapeworms, such as foliate tapeworms, Moniezia expansus, Moniezia benedensis, square tapeworms, stabbed tapeworms, raillietina cesticillus, etc .: Root flagellates of the Protozoa phylum Flagellate, such as Histomonas, protozoal flagellates, such as Leishmania, Trypanosoma, etc., Polychonidae, such as Giardi
  • Amoeba eyes of the fleshy class such as Entamoeba
  • Piroplasma subclasses of the parasitic subclass such as Theilaria, Babesia, etc.
  • Late parasitic subclasses such as Eimeria, Plasmadium, Toxoplasma, etc.
  • the compound of the present invention represented by the above formula (1) is used for exterminating harmful organisms that cause direct harm or discomfort to the human body, or for maintaining public health against harmful organisms that carry or transmit pathogens. Can also be used for.
  • Specific pests include the following.
  • Lepidoptera of the arthropod family Insectidae for example, Sphrageidus similis of the family Spodoptera, Kunugia undans of the family Kaleugaga, Parasa consocia of the family Liga, etc., Takenohosokuroba (Artona martini) Adults, larvae and eggs, etc.; Adults and larvae of the order Coleoptera, such as the longhorn beetle Xanthochroa waterhousei, the blister beetle Epicauta gorhani, and the Staphylinidae Paederus fuscipes.
  • Hymenoptera for example, adults such as Vespa simillima xanthoptera of the wasp family, etc., Brachyponera chinensis of the ant family, etc., larvae and eggs of Betozonellus annulatus, etc.; Flies, such as, for example, mosquitoes (Armigeres subalbatus), Nukaka (Culicoides nipponensis), etc., Chironomus yoshimatsui (Chironomus yoshimatsui), etc., Musciidae (Simulium nikkoense), etc.
  • Ceratopogonidae Hirosia humilis
  • Ceratopogonidae Musca domestica
  • Fanniidae Feannia canicularis
  • Blowfly Phormia regina
  • Ceratopogonidae Sarcophaga peregna
  • Adults, larvae and eggs Adults, larvae and eggs of the order fleas, for example human flea (Pulex irritans) of the family Flea family
  • Adults, larvae and eggs of cockroaches for example, Blattella germanica of the German cockroach family, Periplaneta americana of the cockroaches, Periplaneta fuliginosa, Periplaneta japonica, etc.
  • Orthoptera for example, adults, larvae and eggs of the colgiid family Corydalidae (Diestrammena japonica), cadama (Diestrammena apicalis), etc.
  • Ventricosus etc., Demodex folliculorum, Demodex folliculorum, Dermotophagoides pteronyssinus, Sarcoptes scabiei, etc., Arachnid, Trombicula akamushi, etc. ; Authentic arachnids, for example, Chiracanthium japonicum of the family Araneidae, Heteropoda venatoria of the family Aceridae, Spermophora senoculata of the family Spider spider (Ppercus hiranoidea), Pholcus phalangae (Pholcus phalangae), etc.
  • the compound of the present invention represented by the formula (1) is a pest that damages trees and ornamental plants in agricultural crops, natural forests, artificial forests and urban green areas, such as arthropods, gastropods, nematodes, It is especially valuable to control fungi.
  • the compounds of the invention may be incorporated into other active compounds such as insecticides, acaricides, nematicides, fungicides in their commercially useful formulations and in the use forms prepared by those formulations. It can also exist as a mixture with agents, synergists, plant growth regulators, poison bait or herbicides.
  • Usable forms include wettable powders, wettable granules, dry flowables, water solutions, emulsions, liquids, oils, flowables such as water suspensions/emulsions, capsules, powders, granules and fine powders. Granules, baits, tablets, sprays, fumes, aerosols, etc. can be taken.
  • various pesticide supplements conventionally used in the technical field of agricultural and horticultural chemicals can be appropriately used. Such pesticide aids can be used, for example, for the purpose of improving the effect, stabilizing, and improving the dispersibility of agricultural and horticultural chemicals.
  • Examples of the pesticide auxiliary agent include carriers (diluents), emulsifiers, wettable powders, dispersants, disintegrants and the like.
  • Examples of the liquid carrier include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethyl sulfoxide, and methylnaphthalene. , Cyclohexane, animal and vegetable oils, fatty acids and the like.
  • clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, arabic rubber and the like can be used.
  • ordinary surfactants can be used.
  • higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine and other anionic surfactants can be used.
  • Cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
  • a wetting agent such as dialkyl sulfosuccinate
  • a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol
  • a disintegrant such as sodium lignin sulfonate and sodium lauryl sulfate
  • the compounds of the present invention may be used alone or in combination of two or more as an active ingredient.
  • the content of the compound of the present invention as an active ingredient in these preparations is, for example, 0.01 to 99.5% by mass, preferably selected from the range of 0.5 to 90% by mass, and the formulation form, application method, etc.
  • It may be appropriately determined according to various conditions, but for example, it is about 0.5 to 20% by mass, preferably about 1 to 10% by mass for the powder, and about 1 to 90% by mass, preferably 10 for the wettable powder. It can be produced so as to contain an active ingredient of about 1 to 80% by mass, preferably about 1 to 90% by mass, preferably 10 to 40% by mass of the emulsion.
  • the foliage of the plant should normally be located at the location where damage by these pests is occurring, or where damage may occur.
  • soil whole layer mixing, row application, floor soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dress, rice box treatment, water surface application, etc. It can also be used by absorbing it from. It can also be used by dipping seeds in chemicals, seed powder coating, seed treatment such as calper treatment, application to nutrient solution in nutrient solution (hydroponics) cultivation, smoke or tree trunk injection.
  • the crop or the like may be treated in the state of the preparation.
  • the formulation is diluted with water or without dilution.
  • the method of applying granules to the plant base or nursery for raising seedlings, powder, wettable powder, granule water before sowing or transplanting A method of spraying a disinfectant, granules, etc.
  • Wettable powders, granule wettable powders, water solvents, emulsions, liquid preparations, flowable agents such as suspensions and emulsions in water, capsules, etc. are diluted with water and generally applied at a dose of 5 to 500 liters per 10 ares. Then, it may be sprayed on the soil surface or irrigated into the soil so as to be evenly distributed over the entire area to be treated.
  • Spraying or irrigation may be around seeds or crops / trees that you want to protect from harm. It can also be cultivated during or after spraying to mechanically disperse the active ingredient.
  • the dosage form may differ depending on the application time such as application at the time of sowing, application during the greening period, application at the time of transplantation, etc., for example, powder, granule wettable powder, granule, fine. It may be applied in a dosage form such as granules. It can also be applied by mixing with hilling soil, and it is possible to mix soil with powder, granule wettable powder, granules or fine granules, for example, hilling soil mixing, soil covering mixing, mixing with the entire hilling soil, etc. it can. Alternatively, the soil and various preparations may be applied in layers alternately.
  • solid preparations such as jumbo preparations, pack preparations, granules and granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on paddy fields in a flooded state.
  • an appropriate formulation can be sprayed or injected into the soil as it is or by mixing it with fertilizer or the like.
  • a chemical solution such as an emulsion or a flowable as an inflow source of water into a paddy field such as a water outlet or an irrigation device, it can be applied labor-savingly with the supply of water.
  • a method of seed treatment for example, a method of immersing a seed in a liquid state by diluting or not diluting a liquid or solid preparation to attach and permeate a drug, mixing a solid preparation or a liquid preparation with seeds, Examples thereof include a method of coating the seeds with a powder coating, a method of mixing with an adhesive carrier such as a resin or a polymer and coating the seeds, and a method of spraying the seeds at the same time as planting.
  • the "seed” that performs the seed treatment means a plant body in the early stage of cultivation used for breeding of plants, for example, in addition to seeds, bulbs, tubers, seed potatoes, plant buds, propagules, scales or nutrients for cuttings. Plants for reproduction can be mentioned.
  • the "soil” or “cultivation carrier” of the plant when applied indicates a support for cultivating a crop, particularly a support for growing roots, and the material is not particularly limited, but the plant can be used. Any material that can grow may be used, so-called soil, seedling mat, water, etc., and specific materials include, for example, sand, pebble, vermiculite, diatomaceous soil, agar, gel-like substance, and high molecular weight substance. Examples include rock wool, glass wool, wood chips, and bark.
  • the seedbed for raising seedlings is preferably irrigated with a liquid chemical or sprayed with granules.
  • the compound of the present invention represented by the above formula (1) protects wood (standing wood, fallen wood, processed wood, stored wood or structural wood) from damage by insects such as termites or beetles and fungi. Is also worth it. In such situations, it is possible to control wood or the soil around it by spraying / injecting / irrigating / applying oils, emulsions, wettable powders, sols, and spraying powders, granules, etc. it can. In addition, the oils, emulsions, wettable powders, powders and the like used in this scene are mixed with other active compounds such as insecticides, acaricides, nematodes, bactericides, repellents or synergists.
  • the total amount of active ingredient compounds in these formulations 0.0001-95% by weight, preferably 0.005-10% by weight in oils, powders and granules, emulsions and wettable powders and sols. Can be contained in an amount of 0.01 to 50% by weight.
  • spray 0.01 to 100 g of the active ingredient compound per 1 m 2 on the soil or wood surface.
  • the compound of the present invention represented by the formula (1) is used when a product such as cereals, fruits, nuts, spices and tobacco is stored as it is, in a powdered state or in a state of being mixed in the product. It can be used to protect against the damage of cereals, beetles, mites and fungi. Also, when storing animal products (skin, hair, wool and feathers, etc.) and plant products (cotton, paper, etc.) in their natural or converted state, they are also attacked by Lepidoptera, Coleoptera, stains and cockroaches. It can be protected and can be protected from attacks by Lepidoptera, Coleoptera, flies and mites when storing foods such as meat and fish.
  • a product such as cereals, fruits, nuts, spices and tobacco is stored as it is, in a powdered state or in a state of being mixed in the product. It can be used to protect against the damage of cereals, beetles, mites and fungi.
  • animal products skin,
  • compositions can also be present as a mixture with other active compounds such as pesticides, acaricides, nematodes, fungicides, repellents or synergists, and are included in these formulations.
  • the compound of the present invention represented by the above formula (1) is a disease of humans and livestock, which is parasitic on the body surface of humans and livestock and causes direct harm such as skin feeding or blood feeding.
  • the compound of the present invention is mixed in a small amount of food or feed, or a suitable orally ingestible pharmaceutical composition such as tablets, pills containing a pharmaceutically acceptable carrier or coating substance, Oral administration as a capsule, paste, gel, beverage, medicated feed, medicated drinking water, medicated feed, sustained-release large pills, other sustained-release devices such as those retained in the gastrointestinal tract, or spray, powder, It can be transdermally administered as a grease, cream, ointment, emulsion, lotion, spot-on, pore-on, shampoo or the like. In order to achieve the effect in such an application, the preparation generally contains 0.0001 to 0.1% by weight, preferably 0.001 to 0.01% by weight of the active ingredient compound.
  • a device for example, a collar, a medallion or an ear tag
  • an animal so as to locally or systemically control the arthropod can be used.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used.
  • These use forms are obtained by homogeneously mixing the active ingredient with appropriately milled diluents, fillers, disintegrants and/or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. Manufactured.
  • diluents such as starch, lactose, talc, magnesium stearate, vegetable gums and the like.
  • binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like.
  • Such unit-use formulations can vary widely in the weight and content of the anthelmintic depending on the type of host animal being treated, the degree of infection and the type of parasite and the weight of the host.
  • the final feed When administered by animal feed, it can be uniformly dispersed in the feed, used as a top dressing or in the form of pellets.
  • the final feed contains 0.0001-0.05% by weight, preferably 0.0005-0.01% by weight, of the active ingredient compound.
  • Dissolved or dispersed in a liquid carrier excipient can be administered parenterally to animals by intragastric, intramuscular, intratracheal or subcutaneous injection.
  • the active compound is preferably mixed with a suitable vegetable oil such as peanut oil, cottonseed oil.
  • Such formulations generally contain 0.05-50% by weight, preferably 0.1-5.0% by weight, of the active ingredient compound.
  • the compound of the present invention represented by the above formula (1) has latent pests as an insecticide for arthropods that directly cause harm or arthropods that are vectors of diseases. Spraying / injecting / irrigating / applying oils, emulsions, wettable powders, etc., spraying powders, fumigants, mosquito repellent incense, self-burning smoke agents, chemical reaction smoke agents, etc.
  • Heated fumes, etc. smoke agents such as fogging, treatment of ULV agents, etc., installation of granules, tablets and poisonous bait, or waterways, wells, reservoirs, water tanks and other running water or suspended water of floating powders, granules, etc. It can also be used by a method such as dropping into the water. Furthermore, it is possible to control the damselfish, which is also an agricultural or forest pest, in the same manner as the above-mentioned method, and for fly, etc., to be mixed in the feed of livestock and mixed with feces. For mosquitoes and the like, a method of volatilizing them into the air with an electric mosquito catcher or the like is also effective.
  • the preparations in these usage forms can also exist as a mixture with other active compounds such as pest control agents, mite control agents, nematode control agents, disease control agents, repellents or synergistic agents.
  • the active ingredient compound is contained in these preparations in a total amount of 0.0001 to 95% by weight.
  • the compound of the present invention represented by the above formula (1) can also exist as a mixture with other active compounds. Especially for controlling pests such as arthropods, abdominals, and nematodes that damage plants by mixing with compounds (insecticides) that have pest control activity, mite control activity, or nematode control activity. On the other hand, the number of pests to be controlled can be expanded, and synergistic effects such as reduction of drug dose can be expected. Specific examples of the active compound include the following.
  • Organic phosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, daizinon, dichlorvos, dimeton-S-methyl, dimethoate, Dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, metamidophos, methidathion, monochromotophos.
  • Pyrethroids such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyhalothrin, cyhalothrin, cyphenothrin, cypermethrin, delta deltamethrin), ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalpronate, fluvalinate, flamethrin, halophen Prox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prallethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin) Transfluthrin, etc
  • Insecticides produced by microorganisms such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin. , Polyoxin complex (polioxin), spinetoram (spinetram), spinosad (spinosad), BT agent, etc.; Insecticide derived from natural substances, such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl ester, soybean lecithin, nicotine.
  • Insecticide derived from natural substances such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxypropyl ester, soybean lecithin, nicotine.
  • Nornicotine, oreic acid sodium salt machine oil (petroleum oil), propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch (starch), etc .
  • Other pesticides include, for example, afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz.
  • DBEDC Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt
  • flonicamid flometoquin
  • flufenerim flupyradifurone
  • flupyrimin fluralaner
  • fluralaner fluralaner
  • Hydramethylnon indoxacarb
  • isocycloseram metaflumizone, metaldehyde, nicotin sulfate, oxazosulfyl, pimetrodin (Pymetrozine)
  • pyridalyl pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tycropyrazopyrim etc
  • pyridalyl pyrifluquinqzon
  • spirotetramat sulfoxaflor
  • tolfenpyrad triazamate
  • triflumezopyrim tycropyrazopyr
  • Acaricides such as acequinocyl, asynonapyr, acynonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, bifenazate, binapacryl, phenisobromo.
  • Rate bromopropylate
  • quinomethionat chinomethionat
  • clofentezine clofentezine
  • cienopyrafen cyenopyrafen
  • cyflumethofen cyflumetofen
  • tricyclohexyl tin hydroxide cyhexatin
  • dicofol dicofol
  • dienochlor dienochlor
  • etoxazole ethoxazole
  • Nematicides such as aluminum phosphide, benclothiaz, cadusafos, etoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural.
  • the compound of the present invention represented by the above formula (1) can also exist as a mixture with an active compound other than the compound having pest control activity, mite control activity or nematode control activity.
  • an active compound other than the compound having pest control activity, mite control activity or nematode control activity.
  • mite control activity or nematode control activity.
  • the control labor can be reduced and the amount of drug can be reduced.
  • a synergistic effect can also be expected. Further, by using it in combination with a repellent or a synergistic agent, a more effective control effect such as a synergistic effect can be expected.
  • a disease control agent for example, DD (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, andoprim, anilazine, azaconazole , Azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb-isopropyl, benthiazole, bitertanol , Bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, buthiobate, calcium polysulfide, captafol ( captafol), captan, carbendazim, carboxin, carpropamid, quinomethionat, chlorfenazole, chloroneb, chloropicrin, chlorothalonil.
  • DD 1,3-dichloropropene
  • acibenzolar-S-methyl aldimorph
  • Chlozolinate, DBEDC complex of bis (ethylenediamine) copper-bis- (dodecylbenzenesulfonic acid)
  • cupper hydroxide copper nonylphenol sulfonate (copper nonylphenol sulfonate), copper chloride (copper) Oxychloride)
  • cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodin il dazomet, diclobutrazol, dichloflurazol, dichlofluanid, dichlone, diclocymet, diclomezine, dicloezine, diethofencarb, diflunoconazole, diflunoconazole, difenoconazole, difenoconazole.
  • edifenphos enestrobin, epoxyconazole, epoxiconazole, etaconazole, ethaboxam, shiitake mycelium extract from extract, famoxadone, fenamidone, fenamidone ), Fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone (Ferimzone), fluazinam, flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin , Fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, holpet (fo) lpet), fosetyl-aluminum (fosetyl-AL), fthalide, fuberidazole,
  • Aclonifen As a compound having herbicidal activity, for example, Aclonifen, acifluofen-sodium, alachlor, alloxydim, amicabazone, amidosulfuron, anilofos, ashlam, atrazine (aclonifen), acifluofen-sodium, alaclor atrazine), azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos ), Bifenox, bromobutide, bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, clomeprop Cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclohop-methyl, diflufenican, diflufenican, dime
  • prohydrojasmon thidiazuron
  • trinexapac uniconazole-P
  • wax etc.
  • Repellents For example, capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene.
  • Colytic agents such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin Etc. can be mentioned.
  • the compounds of the present invention can be used as biopesticides, for example, cytoplasmic polyhedrosis virus (CPV), insect poxvirus (EPV), granulosis virus (GV), nuclear polyhedrosis virus (Nuclear).
  • Virus preparations such as polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monoacrosporium phymatophagum, Paecilomyus pesopaspeus Peorosepeus Pearosepeus apespas , Steinernema carpocapsae, Steinernema glasseri, Steinernema kushidai, Verticillium lecanii, etc.
  • CPV cytoplasmic polyhedrosis virus
  • EPV insect poxvirus
  • GV granulosis virus
  • Nuclear nuclear polyhedrosis virus
  • Virus preparations such as polyhedrosis virus (NPV), Beauveria bassiana
  • insecticides such as Verticillium lecanii Micropesticide, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, and other microbial pesticides used as fungicides.
  • insecticides such as Verticillium lecanii Micropesticide, Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, and other
  • biological pesticides for example, Amblyseius californicus, Amblyseius cucumeris, Degenerans amblyseius degenans, Aphidius colemani, Aphimyleta spp.
  • Hamoglyco mayu bee (Dacnusa sibirica), Isaea Himekobachi (Diglyphus isaea), Onshitsuyakobachi (Encarsia formosa), Sabakutsuyakobachi (Eretmocerus eremicus), Arigatashima Azami horse (Frank) Black-spotted bee (Hemiptarsenus varicornis), leaf-spotted wasp (Neochrysocharis formosa), long-spotted beetle (Orius sauteri), oriental leaf-spotted beetle (Phytoseius oyosyou) (Phytosei miuyosyo) Natural enemy creatures such as varius, codlelure, cuelure, geraniol, gyptol, liblure, looplure, methyleugenol, orfralure, It is also possible to use in combination with pheromone agents such as varius, codlelure
  • Emulsion Compound of the present invention (10 parts), xylene (60 parts), N-methyl-2-pyrrolidone (20 parts), Solpol 3005X (mixture of nonionic surfactant and anionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 2 Wettable powder-1 Compound of the present invention (20 copies), Nipseal NS-K (White Carbon, Toso Silica Co., Ltd., trade name) (10 copies), Kaolin Clay (Kaolinite, Takehara Chemicals Co., Ltd., trade name) (60 copies) , Sun Extract P-252 (sodium lignin sulfonate, Nippon Paper Chemicals Co., Ltd., trade name) (5 copies) and Lunox P-65L (alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (5 copies) was uniformly mixed and pulverized with an air mill to obtain a wettable powder.
  • Nipseal NS-K White Carbon, Toso Silica Co., Ltd., trade name
  • Kaolin Clay Kaolin Clay
  • Sun Extract P-252 sodium lignin sulfonate, Nippon Paper Chemicals Co., Ltd., trade name
  • Lunox P-65L alkylallyl sul
  • Formulation Example 3 Wettable powder-2 Compound of the present invention (20 parts), Nipseal NS-K (White Carbon, Toso Silica Co., Ltd., trade name) (20 parts), Kaolin Clay (50 parts), Lunox 1000C (Surfactant Condensate, Toho Kagaku) Kogyo Co., Ltd., trade name) (5 parts) and Solpol 5276 (nonionic surfactant, Toho Kagaku Kogyo Co., Ltd., trade name) (5 parts) are uniformly mixed and pulverized with an air mill to prepare a wettable powder. Obtained.
  • Formulation Example 4 Water solvent-1 The compound of the present invention (20 parts), Lunox P-65L (alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name) (3 parts), and water-soluble carrier (potassium chloride) (77 parts) are uniformly mixed and pulverized. Then, an aqueous solvent was obtained.
  • Lunox P-65L alkylallyl sulfonate, Toho Chemical Industry Co., Ltd., trade name
  • water-soluble carrier potassium chloride
  • Flowable Agent-1 The present invention is added to a premixed mixture of propylene glycol (5 parts), slurry 7933 (anionic surfactant, Toho Kagaku Kogyo Co., Ltd., trade name) (5 parts), and water (50 parts).
  • the compound (20 parts) was dispersed to form a slurry-like mixture, and then the slurry-like mixture was wet-ground with Dynomill (Symmal Surfactant), and then xanthan gum (0.2 parts) was well mixed with water (19.8 parts) in advance. What was mixed and dispersed was added to obtain a flowable agent.
  • Formulation Example 7 Flowable Agent-2 Compound of the present invention (20 parts), Newkalgen FS-26 (mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name) (5 parts), propylene glycol (8 parts), Water (50 parts) was mixed in advance, and this slurry mixture was wet-milled with Dynomill (Shinmaru Enterprises Co., Ltd.). Next, xanthan gum (0.2 parts) was well mixed and dispersed in water (16.8 parts) to prepare a gel-like material, which was thoroughly mixed with the crushed slurry to obtain a flowable agent.
  • Newkalgen FS-26 mixture of dioctyl sulfosuccinate and polyoxyethylene tristyryl phenyl ether, Takemoto Yushi Co., Ltd., trade name
  • propylene glycol 8 parts
  • Water 50 parts
  • Dynomill Shinmaru Enterprises Co
  • Formulation Example 8 EW-1
  • the compound of the present invention (20 parts), Solpol CA-42 (nonionic surfactant, Toho Chemical Industry Co., Ltd., trade name) (15 parts) and preservative Proxel GX-L (0.1 parts) are mixed and homogenized. After that, water (59.6 parts) was gradually added with stirring to obtain a dispersion.
  • Xanthan gum obtained by adding antifoaming agent Antihome E-20 (emulsion type modified silicone type, Kao Corporation, trade name) (0.1 part) to the obtained dispersion and dispersing it in propylene glycol (5.0 parts). (0.2 parts) was added to obtain an emulsion preparation (phase inversion emulsification method).
  • Formulation Example 14 Granule-2 A compound of the present invention (5 parts), sodium lignin sulfonate (4 parts), polyvinyl alcohol (PVA) (PVA) (PVA) (PVA) 0.5 part) and white carbon (0.5 part) were added, coated, and then dried and sized to obtain granules.
  • PVA polyvinyl alcohol
  • PVA polyvinyl alcohol
  • PVA polyvinyl alcohol
  • white carbon 0.5 part
  • Formulation Example 15 Granules-3 Ishikawa Wright (89 parts) was put into a tumbling type granulator to make it water-containing, and then the compound of the present invention (5 parts), sodium ligninsulfonate (3 parts), and sodium dioctylsulfosuccinate, which had been pulverized and mixed in advance, were mixed. (0.5 parts), POE styryl phenyl ether (2 parts) and polyvinyl alcohol (PVA) (0.5 parts) were added, coated and dried to obtain granules.
  • PVA polyvinyl alcohol
  • Fine Granules-1 The compound of the present invention (2 parts) was diluted with a solvent, and the pumice stone (98 parts) as a bulking agent was mixed while spraying the diluted solution. The obtained granular composition was dried and then sieved to obtain a fine granule.
  • Fine granule-2 The compound of the present invention (5 parts) is air-milled or mechanochemically milled if necessary. After uniformly mixing the powdered bulk material and silica sand (85 parts) as an bulking agent, the binder Toxanone GR-31A (10 parts) diluted with a solvent was mixed while spraying, and the obtained granular composition was dried. Then, it was sieved to obtain a fine granule.
  • Formulation Example 18 Dust The compound of the present invention (5 parts), white carbon (5 parts) and clay (trade name of Nippon Talc Co., Ltd.) (90 parts) were uniformly mixed and pulverized to obtain a powder.
  • Formulation Example 19 DL powder A compound of the present invention (5 parts), propylene glycol (0.5 parts) and DL clay (94.5 parts) were uniformly mixed and pulverized to obtain a powder.
  • Formulation Example 20 Seed coating powder uniform the compound of the present invention (10 parts), sodium lignin sulfonate (6 parts), polyvinyl alcohol (PVA) (1 part) and clay (trade name of Nippon Tarku Co., Ltd.) (83 parts). The powder prepared by mixing and pulverizing the seeds and the seeds moistened in advance were mixed and air-dried to obtain coated seeds.
  • PVA polyvinyl alcohol
  • clay trade name of Nippon Tarku Co., Ltd.
  • Comparative agent A No. 6 described in JP-A-8-073436
  • Test Example 1 Effect on sweet potato root-knot nematode (Meloidogyne incognita (Kofoid et White) Chitwood) 200 ml of test soil adjusted to 200 nematodes / 20 g of soil was placed in a styrene cup (9 cm in diameter and 6.5 cm in height). After 50 ml of a water-diluted solution (100 ppm) of the emulsion prepared according to Formulation Example 1 was irrigated, tomatoes were seeded (13 seeds/pot). After sowing, it was grown in a greenhouse.
  • Root bump index ⁇ (root hump degree x number of relevant shares) / (4 x number of surveyed shares)
  • Control value (%) [1-(root Cobb index of treated area/root Cobb index of untreated area)] x 100
  • Test Example 2 Test of insecticidal effect by irrigation treatment of cucumber cotton aphid (Aphis gosiipii Glover) Leaf pieces infested with 50 to 80 aphid adult larvae were inoculated on leaves of pot-planted cucumber seedlings grown for 2 weeks after sowing. .. A water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was irrigated on the root of a cucumber seedling infested with aphids the day after inoculation. On the 7th day after the treatment, the number of parasitic aphids was investigated, and the control rate was calculated according to the following formula. The test was carried out by using one seedling in each group.
  • Control rate (%) (1-A / B x D / C) x 100
  • the compound of the invention showed a control rate of 80% or more.
  • Comparative Agent A had a control rate of 0%.
  • Test Example 3 Insecticidal effect test on cucumber cotton aphid (Aphis gosiipii Glover) by spraying 50 to 80 adult aphid larvae infested the leaves of pot-planted cucumber seedlings raised for 2 weeks after sowing. ..
  • a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed on the leaf stems of aphid-parasitized cucumber seedlings on the day after inoculation using an air brush.
  • the number of parasitic aphids was investigated, and the control rate was calculated according to the following formula. The test was carried out by using one seedling in each group.
  • Control rate (%) (1-A / B x D / C) x 100
  • 90% or more of the compounds of the present invention of compound numbers A-66, A-70, A-71, A-74, A-252, A-253, A-254 The control rate of was shown.
  • the comparative agent A had a control rate of 0%.
  • Test Example 4 A polyethylene cup having a capacity of 430 ml containing test water for killing imagoes against tomato rust mites (Aculops lycopersici Massee) was covered with a lid having a hole (diameter about 5 mm) in the center. A circular filter paper with a diameter of 6.5 cm was cut into a notch having a width of about 5 mm, and a strip-shaped portion hung downward was inserted so as to be immersed in water in the cup through the hole in the lid, and absorbent cotton was placed on the filter paper.
  • control rate 100%
  • 80 unsame: 99-80%
  • 50 unsame: 79-50%)
  • 0 unsame: less than 50%
  • Control rate (A x 100 + B x 80 + C x 50) / (A + B + C + D)
  • the compounds of the present invention of A-190, B-3, B-21, B-34, B-54 and B-55 showed a control rate of 100%.
  • the comparative agent A had a control value of 0%.
  • Test Example 5 Density Suppression Test Against the Ticked Mite (Tetranychus urticae Koch)
  • Ticked Mite Tetranychus urticae Koch
  • a 430 ml-volume polyethylene cup containing water was covered with a lid having a hole (about 5 mm in diameter) in the center.
  • a circular filter paper with a diameter of 6.5 cm was cut into a notch having a width of about 5 mm, and a strip-shaped portion hung downward was inserted so as to be immersed in water in the cup through the hole in the lid, and absorbent cotton was placed on the filter paper.
  • next-generation density suppression effect on eggs laid by adults 7 days after the treatment was 100 (density suppression rate: 100%), 95 (same: 99-95%), 80 (same: 94-80%), 50 (same: Evaluation was made on a scale of 5 (79-50%) and 0 (same: less than 50%), and the next-generation density suppression rate was calculated by the following formula based on the results. The test was carried out using 1 cup of each section.
  • Next-generation density suppression rate (A x 100 + B x 95 + C x 80 + D x 50) / (A + B + C + D + E)
  • compound numbers A-17, A-18, A-29 , A-33, A-34, A-38, A-74, A-75, A-82 of the present invention showed a density suppression rate of 100%.
  • the comparative agent A had a density suppression rate of 0%.
  • Test Example 6 A 430 ml capacity polyethylene cup containing test water for killing imago against Panonychus citri McGregor was covered with a lid having a hole (diameter about 5 mm) in the center. A circular filter paper with a diameter of 6.5 cm was cut into a notch having a width of about 5 mm, and a strip-shaped portion hung downward was inserted so as to be immersed in water in the cup through the hole in the lid, and absorbent cotton was placed on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from fully expanded leaves of citrus fruits were placed on absorbent cotton in which the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs. Was inoculated.
  • This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and 2.0 ml per cup of a water dilution (500 ppm) of the emulsion prepared according to Formulation Example 1 was sprayed using an air brush. After spraying, it was kept in a thermostatic chamber at 25°C.
  • Insecticidal rate (%) (number of dead larvae / number of test larvae) x 100
  • Insecticidal rate (%) (number of dead larvae / number of test larvae) x 100
  • Insecticidal rate (%) (number of dead larvae / number of test larvae
  • Test Example 7 Largicidal test against Thrips palmi Karny Thrips palm leaves of pot plants planted for 2 weeks after sowing were dried with a water-diluted solution (500 ppm) of the emulsion prepared according to Formulation Example 1 in air. A sufficient amount was sprayed using a brush. After air-drying the drug solution, inoculate about 7mm x 7mm filter paper inoculated with about 50 thrips eggs so that the eggs touch the cucumber cotyledons, and put in a dish case (65mm x 65mm, height 95mm) (1 Strain / case), kept in a constant temperature room at 26 ° C. Six days after treatment, the number of surviving insects was investigated in the following grades.
  • the compounds of the present invention of Compound Nos. A-31, A-84, A-124, A-190, B-29, B-37, and C-35 showed a control rate of 90% or more.
  • Comparative Agent A had a control rate of 0%.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Agronomy & Crop Science (AREA)
  • Soil Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé qui peut être utilisé en tant qu'agent agricole et horticole, spécifiquement en tant qu'agent de lutte contre les nuisibles ou agent de lutte contre les nématodes pour des utilisations agricoles et horticoles. Le composé est un dérivé d'hydrazine représenté par la formule générale (I) ou un sel associé. [où R1, R2, R3, X, n, Y1, Y2, Y3, et Y4 sont tels que décrits dans les revendications].
PCT/JP2020/009685 2019-03-06 2020-03-06 Nouveau dérivé d'hydrazone et agents agricoles et horticoles l'utilisant comme principe actif Ceased WO2020179910A1 (fr)

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Publication number Priority date Publication date Assignee Title
JPWO2023282110A1 (fr) * 2021-07-08 2023-01-12
WO2025090578A1 (fr) 2023-10-26 2025-05-01 Fmc Corporation Hydrazones hétérocycliques utilisées en tant que nématicides
TWI900783B (zh) 2021-07-08 2025-10-11 日商石原產業股份有限公司 殺線蟲組成物

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WO2025018390A1 (fr) * 2023-07-18 2025-01-23 アグロカネショウ株式会社 Nouveau dérivé d'hydrazone et agent pour une utilisation agricole et horticole le contenant en tant que principe actif

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GB1533706A (en) * 1976-03-01 1978-11-29 Ici Ltd Fungicidal imidazoles and 1,2,4-triazoles
JPH07138233A (ja) * 1993-11-12 1995-05-30 Ishihara Sangyo Kaisha Ltd ヒドラゾン系化合物又はその塩、それらの製造方法及びそれらを有効成分として含有する有害生物防除剤
JPH0873436A (ja) * 1994-07-06 1996-03-19 Nissan Chem Ind Ltd セミカルバゾン誘導体
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Cited By (7)

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Publication number Priority date Publication date Assignee Title
JPWO2023282110A1 (fr) * 2021-07-08 2023-01-12
WO2023282110A1 (fr) 2021-07-08 2023-01-12 石原産業株式会社 Composition nématocide
KR20240032841A (ko) 2021-07-08 2024-03-12 이시하라 산교 가부시끼가이샤 살선충 조성물
EP4368023A4 (fr) * 2021-07-08 2025-05-14 Ishihara Sangyo Kaisha, Ltd. Composition nématocide
TWI900783B (zh) 2021-07-08 2025-10-11 日商石原產業股份有限公司 殺線蟲組成物
JP7776761B2 (ja) 2021-07-08 2025-11-27 石原産業株式会社 殺線虫組成物
WO2025090578A1 (fr) 2023-10-26 2025-05-01 Fmc Corporation Hydrazones hétérocycliques utilisées en tant que nématicides

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