WO2020251012A1 - Nouveau dérivé de 1-benzylamine et agents agricoles et horticoles l'utilisant comme principe actif - Google Patents

Nouveau dérivé de 1-benzylamine et agents agricoles et horticoles l'utilisant comme principe actif Download PDF

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WO2020251012A1
WO2020251012A1 PCT/JP2020/023191 JP2020023191W WO2020251012A1 WO 2020251012 A1 WO2020251012 A1 WO 2020251012A1 JP 2020023191 W JP2020023191 W JP 2020023191W WO 2020251012 A1 WO2020251012 A1 WO 2020251012A1
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haloalkyl
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響 八田
一秋 小山
恒一 荒木
祥 森下
福地　俊樹
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Agro Kanesho Co Ltd
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00—Preparation of sulfones; Preparation of sulfoxides
    • C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
    • C07C321/28—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain

Definitions

  • the present invention relates to a novel 1-benzylamine derivative and an agricultural and horticultural agent containing the compound as an active ingredient, particularly an agricultural and horticultural pest control agent, a mite control agent, a nematode control agent, or an agricultural and horticultural disease control agent, and the like. It is about how to use.
  • Patent Document 1 describes that a 1-benzylpiperidine derivative is useful as an acaricide for animals.
  • Patent Document 1 does not disclose a compound in which a sulfur substituent as in the present invention is specifically introduced as a substituent at the 5-position of the phenyl group of the 1-benzylpiperidin derivative.
  • Patent Document 1 it was found that their effects on spider mites were insufficient.
  • the following compounds are disclosed as compound analogs of the present invention (for example, Patent Documents 2 to 3). However, all of these compounds disclosed in Patent Documents 2 to 3 have different chemical structures from the compounds of the present invention.
  • the present invention has been completed by finding that it is useful as a horticultural pest control agent, a mite control agent, a nematode control agent or a disease control agent. That is, the present invention relates to an agricultural and horticultural drug containing a 1-benzylamine derivative represented by the following formulas (1) to (2), its N-oxide or a salt thereof as an active ingredient, a method of using the same, and a method of producing the same. It is a thing.
  • R 1 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, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group, n indicates an integer from 0 to 2 X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkyloxycarbonyl group, C 1-6 alkoxymethyl group, formyl
  • R 2a , R 2b , R 2c and R 2d may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
  • J 1 indicates direct binding
  • R 4a and R 4b may be the same or different, respectively, and represent a hydrogen atom, a halogen atom, a C 1-6 alkyl group, a C 1-6 haloalkyl group, a cyano group or a C 1-6 alkoxycarbonyl group.
  • R 5 is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 alkoxycarbonyl group, a C 1-6 alkylcarbonyl group, a C 1-6 haloalkylcarbonyl group, a C 1-6 alkylsulfonyl group or C 1-6 shows a haloalkylsulfonyl group.
  • R 1 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, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group, n indicates an integer from 0 to 2 X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkyloxycarbonyl group, C 1-6 alkoxymethyl group, formyl
  • R 6 and R 7 may be the same or different, hydrogen atom, C 1-6 alkyl group, C 1-6 haloalkyl group, cyano group, cyano C 1-6 alkyl group, C 2-6 alkenyl group, C. 2-6 alkynyl group, C 2-6 haloalkenyl group, C 2-6 haloalkynyl group, phenyl group optionally substituted with one or more with R 8 , C 1-3 alkylphenyl group (at this time, the phenyl group is Indicates a C 3-6 cycloalkyl group which may be substituted at least one with R 9 ) or at least one with R 10 .
  • R 8 represents a halogen atom, C 1-6 alkyl group or C 1-6 haloalkyl group.
  • R 9 represents a halogen atom, C 1-6 alkyl group or C 1-6 haloalkyl group.
  • R 10 represents a halogen atom, a C 1-6 alkyl group or a C 1-6 haloalkyl group.
  • 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, a mite control agent, a nematode control agent or a disease control agent. It is also effective against pests that parasitize pet animals such as dogs and cats, and livestock such as cows and sheep.
  • the "halogen atom” means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom, and is a "C 1-6 alkyl group".
  • C 3-6 cycloalkyl Indicates a linear or branched alkyl group having 1 to 6 carbon atoms substituted with one or more halogen atoms which may be the same or different, and "C 3-6 cycloalkyl” is , For example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., which have 3 to 6 cyclic carbon atoms, preferably 3 to 4 cycloalkyl groups.
  • Examples of the C 1-6 haloalkyl group include fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 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-fluorobutyl group, 4-chlorobutyl, nonaflu
  • Examples of the C 2-6 alkenyl group include vinyl group, allyl group, isopropenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-pentenyl group and 3-pentenyl group.
  • 4-Pentenyl group 1,1-dimethyl-2-propenyl group, 1-ethyl-2-propenyl group, 1-methyl-2-butenyl group, 1-methyl-3-butenyl group, 2-hexenyl group, 3- Number of carbon atoms having at least one double bond at any position such as hexenyl group, 4-hexenyl group, 5-hexenyl group, 1,1-dimethyl-2-butenyl group, 1,1-dimethyl-3-butenyl group, etc. Examples thereof include 2 to 6, preferably 2 to 4 linear or branched alkenyl groups.
  • Examples of the C 2-6 haloalkenyl group include 1-fluorovinyl group, 2-fluorovinyl group, 2,2-difluorovinyl group, 3-chloro-2-propenyl group, 3,3-difluoro-2-allyl group, and the like. 3,3-Dichloro-2-allyl group, 4,4,4-trifluoro-2-butenyl group, 4,4,4-trifluoro-3-butenyl group, 5-chloro-3-pentenyl group, 6- Linear with 2 to 6 carbon atoms substituted with 1 to 9, preferably 2 to 5 halogen atoms having at least one double bond at any position, such as a fluoro-2-hexenyl group. Alternatively, a branched chain alkenyl group can be mentioned.
  • 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- 2 to 6 carbon atoms having at least one triple bond at any position such as butynyl group, 1,1-dimethyl-3-butynyl group, 1-methyl-3-pentynyl group, 1-methyl-4-pentynyl group, etc.
  • C 2-6 haloalkynyl groups include fluoroethynyl group, 4,4,4-trifluoro-2-butynyl group, 5,5,5-trifluoro-3-pentynyl group, 1-methyl-3,3, 1-9, preferably 2-5, having at least one triple bond at any position, such as a 3-trifluoro-2-butynyl group, a 1-methyl-5,5,5-trifluoro-2-pentynyl group, etc.
  • Examples thereof include a linear or branched alkynyl group having 2 to 6 carbon atoms substituted with one halogen atom.
  • Examples of the C 1-6 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentoxy group and an n-hexyloxy group.
  • Examples thereof include a linear or branched alkoxy group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as a group.
  • 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-.
  • 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. , Cyclobutylmethyl, cyclopentylmethyl and the like.
  • C 3-6 preferable number of carbon atoms of the C 3-6 cycloalkyl group and C 1-6 alkyl group constituting the cycloalkyl C 1-6 alkyl group are the same as those defined above.
  • C 3-6 halocycloalkyl C 1-6 alkyl groups include, for example, 1-fluorocyclopropylmethyl, 2-fluorocyclopropylmethyl, 2,2-difluorocyclopropylmethyl, 2-chlorocyclopropylmethyl, 2, 2-Dichlorocyclopropylmethyl, 2- (2,2-difluorocyclopropyl) ethyl, 2- (2,2-dichlorocyclopropyl) ethyl, 3- (2,2-difluorocyclopropyl) propyl, 4- (2) , 2-difluorocyclopropyl) butyl, 5- (2,2-dichlorocyclopropyl) pentyl, 6- (2,2-difluorocyclopropyl) hexyl, 2,2-difluorocyclobutylmethyl, 2,2-dichlorocyclo Examples thereof include groups such as butylmethyl, 3,3-difluorocyclopentylmethyl, 3,3-
  • 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.
  • the preferred number of carbon atoms of the C 1-6 alkoxy group constituting the C 1-6 alkoxycarbonyl group is as previously described.
  • the contents of the C 1-6 alkoxy group in C 1-6 alkoxymethyl group is as described above.
  • the contents of the C 1-6 alkyl group in the C 1-6 alkyl carbonyl group are as described above.
  • C 1-6 haloalkyl groups in C 1-6 haloalkylcarbonyl group is as described above.
  • the contents of the C 1-6 alkyl group in the C 1-6 alkyl sulfonyl group are as described above.
  • the contents of C 1-6 haloalkyl groups in C 1-6 haloalkylsulfonyl group is as described above.
  • Examples of the salt of the 1-benzylamine derivative represented by the formula (1) or (2) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates and fumarates. , Maleate, oxalate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and other organic acid salts can be exemplified.
  • the 1-benzylamine derivative represented by the above formula (1) or (2) of the present invention may contain one or more asymmetric centers in its structural formula, and two or more kinds of optical isomers may be contained.
  • the present invention also includes all optical isomers and mixtures containing them in arbitrary proportions.
  • the 1-benzylamine derivative represented by the above formula (1) or (2) of the present invention may have two kinds of geometric isomers derived from a carbon-carbon double bond in its structural formula.
  • the present invention also includes all geometric isomers and mixtures containing them in arbitrary proportions.
  • reaction equation 1 [In the equation, X, Y and R 1 are as defined in the equation (1). ]
  • the 3-sulfinylbenzaldehyde derivative represented by the above formula (9) can be produced by the oxidation reaction of the 3-sulfanylbenzaldehyde derivative represented by the above formula (8).
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Hydrocarbon solvents examples include alcohol solvents such as methanol and ethanol, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N, N-dimethylformamide, acetonitrile and propio.
  • examples thereof include nitrile solvents such as nitrile, aprotonic polar solvents such as N-methylpyrrolidone, N, N'-dimethylimidazolinone, carboxylic acids such as acetic acid, and water.
  • 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 oxidizing agent used in the oxidation reaction of the 3-sulfanylbenzaldehyde compound represented by the formula (8) include m-chloroperbenzoic acid, sodium periodate, hydrogen peroxide, and tert-hypochlorite. Examples include butyl and sodium hypochlorite.
  • Such an oxidizing agent can be used in an amount usually 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the 3-sulfanylbenzaldehyde derivative represented by the above formula (8).
  • 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 0 ° C. to room temperature.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, 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 ordinary purification means.
  • the 3-sulfanylbenzaldehyde derivative represented by the formula (8) used in the above reaction can be produced, for example, by the method described in Patent Document 2. It can also be produced by a method described in known literature, for example, Molecules. 2015, 20, 5409-5422.
  • Reaction equation 2 [In the equation, X, Y, n, R 1 , R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in the equation (1). ]
  • the 1-benzylamine derivative represented by the formula (1) is a benzaldehyde derivative represented by the formula (4) and an amine represented by the formula (5).
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Carbide-based solvent ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion.
  • Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned.
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required. In particular, it is preferable to use a mixture of a small amount of acetic acid and another inert solvent.
  • a known boron hydride compound and a salt thereof, or an aluminum hydride compound can be used as the reducing agent used in the reaction between the compound of the formula (4) and the compound of the formula (5).
  • the boron hydride compound and a salt thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like.
  • Examples of the aluminum hydride compound include lithium aluminum hydride and diisopyrropyrua hydride.
  • Such a reducing agent can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
  • 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 unequivocally determined, 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 ordinary purification means.
  • Reaction equation 3 [In the equation, X, Y, n, R 1 , R 6 and R 7 are as defined in the equation (2). ]
  • the 1-benzylamine derivative represented by the formula (2) is the benzaldehyde derivative represented by the formula (4) and the amines represented by the formula (6).
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Carbide-based solvent ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion.
  • Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned.
  • One of these solvents can be used alone, or two or more of these solvents can be mixed and used as required. In particular, it is preferable to use a mixture of a small amount of acetic acid and another inert solvent.
  • a known boron hydride compound and a salt thereof, or an aluminum hydride compound can be used as the reducing agent used in the reaction between the compound of the formula (4) and the compound of the formula (6).
  • the boron hydride compound and a salt thereof include borane, borane-tetrahydrofuran complex, borane-2-methylpyridine complex, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride and the like.
  • Examples of the aluminum hydride compound include lithium aluminum hydride and diisopyrropyrua hydride.
  • Such a reducing agent can be used in an amount usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the formula (4).
  • the ratio of the benzaldehyde compound represented by the formula (4) to the amines represented by the formula (6) is 1 to 2 mol of the compound of the formula (6) with respect to the compound of the formula (4). It is more preferable to use.
  • 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 unequivocally determined, 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 ordinary purification means.
  • R 1 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, C 3 -6 Cycloalkyl C 1-6 alkyl group or C 3-6 halocycloalkyl C 1-6 alkyl group, n indicates an integer from 0 to 2 X is, C 1-6 alkyl, C 1-6 haloalkyl group, C 3-6 cycloalkyl alkyl groups, C 2-6 alkenyl groups, C 2-6 alkynyl group, C 2-6 haloalkenyl, C 2- 6 Haloalkynyl group, C 1-6 alkoxy group, C 1-6 haloalkoxy group, C 3-6 halocycloalkyl group, C 1-6 alkoxycarbonyl group, C 1-6 alkoxymethyl group, formyl group
  • the 1-benzyl alcohol derivative represented by the formula (3) is the benzaldehyde derivative represented by the formula (4) and NaBH 4 , NaBH (OAc) 3 or NaBH 3 CN.
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane, aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Carbide-based solvents such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvents such as methyl acetate and ethyl acetate, alcohol-based solvents such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion.
  • Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned.
  • the NaBH 4 , NaBH (OAc) 3 or NaBH 3 CN used in the reaction is usually 1 to 100 equivalents, preferably 1 to 2 equivalents, relative to the benzaldehyde compound represented by the above formula (3). Can be used in quantity.
  • 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 unequivocally determined, 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 ordinary purification means.
  • Reaction equation 5 [In the formula, X, Y, n, R 1 , R 2a , R 2b , R 2c , R 2d , M, J 1 and J 2 are as defined in formula (1), and Z is methanesulfonyl. Indicates a group or a trifluoromethanesulfonyl group.
  • the compound represented by the formula (7) is a benzyl alcohol derivative represented by the formula (3) and methanesulfonyl chloride or trifluoromethanesulfonyl chloride, which is a base such as triethylamine. It can be produced by reacting in the presence of an inert solvent such as dichloromethane.
  • the benzylamine derivative represented by the formula (1) is prepared by combining the compound represented by the formula (7) and the amines represented by the formula (5) in an inert solvent in the presence of an appropriate base. It can be produced by reacting with.
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Carbide-based solvent ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion.
  • Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned.
  • 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 base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (5) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide, and the like. Triethylamine and the like are preferable.
  • the ratio of bases used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (5) is 1 to 2 times that of the compound represented by the formula (7). It is more preferable to use a molar amount.
  • the reaction can usually be carried out in the range from ⁇ 78 ° C.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, 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 ordinary purification means.
  • Reaction equation 6 [In the formula, X, Y, n, R 1 , R 6 and R 7 are as defined in the formula (2), and Z represents a methanesulfonyl group or a trifluoromethanesulfonyl group. ]
  • the compound represented by the formula (7) is a benzyl alcohol derivative represented by the formula (3) and a base such as triethylamine and methanesulfonyl chloride or trifluoromethanesulfonyl chloride. It can be produced by reacting in an inert solvent such as dichloromethane in the presence of. Further, the 1-benzylamine derivative represented by the formula (2) inactivates the compound represented by the formula (7) and the amines represented by the formula (6) in the presence of an appropriate base. It can be produced by reacting in a solvent.
  • a solvent inert to the reaction can be widely used.
  • aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane and heptane
  • aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene and xylene, halogenation of methylene chloride, 1,2-dichloroethane and chloroform.
  • Carbide-based solvent ether-based solvent such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ester-based solvent such as methyl acetate and ethyl acetate, alcohol-based solvent such as methanol, ethanol, propanol and isopropanol, acetic acid, formic acid and propion.
  • Carboxylic acid solvent such as acid, amide solvent such as N, N-dimethylformamide, nitrile solvent such as acetonitrile and propionitrile, aprotonic polar solvent such as N-methylpyrrolidone and N, N'-dimethylimidazolinone. Etc. can be mentioned.
  • 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 base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (6) include potassium carbonate, cesium carbonate, oily sodium hydride, sodium hydroxide or. Triethylamine and the like are preferable.
  • the ratio of the base used in the reaction between the compound represented by the formula (7) and the amines represented by the formula (6) is 1 to 2 times the molar amount of the base compared to the compound of the formula (7). It is more preferable to use the amount.
  • the reaction can usually be carried out in the range from ⁇ 78 ° C.
  • the reaction time varies depending on the reaction temperature and the like and cannot be unequivocally determined, 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 ordinary purification means.
  • Typical compounds of 1-benzyl alcohols represented by the above formula (3) are illustrated in Table 5, but the present invention is not limited thereto.
  • the physical properties in the table indicate the properties and the melting point (° C.), where "n-" indicates a normal, “Me” indicates a methyl group, and “Pr” indicates a propyl group.
  • Typical compounds of benzaldehydes represented by the above formula (4) are illustrated in Table 6, but the present invention is not limited thereto.
  • the physical properties in the table indicate the properties and the melting point (° C.), where "n-" indicates a normal, “Me” indicates a methyl group, and “Pr” indicates a propyl group.
  • the compounds of the present invention can be used in agriculture, indoors or in forests for the prevention and extermination 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 compounds of the present invention include agricultural crops, for example, edible crops (wheat such as rice, barley, wheat, rye, oat, corn, potatoes, sweet potatoes, satoimo, soybeans, red beans, sora beans, red beans, green beans, peanuts, etc.
  • vegetables cabbage, white vegetables, radish, buds, broccoli, cauliflower, komatsuna and other Abrana crops, pumpkin, cucumber, squid, makuwauri, melon and other crops, eggplant, tomato, pepper, pepper , Okura, spinach, lettuce, brick, carrot, gobo, garlic, onion, onion, etc.), mushrooms (shitake, mushroom, etc.), fruit trees / fruits (apple, citrus, pear, grape, peach, plum) , Cherry blossoms, walnuts, chestnuts, almonds, bananas, strawberries, etc.), fragrances, etc.
  • Appreciation crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, beans, sugar cane, hops, etc.) Cotton, hemp, olive, rubber, coffee, etc.), grass and feed crops (timothy, clover, alfalfa, corn, sorghum, orchardgrass, rice grass, bean grass, etc.), turf (Koryo turf, bentgrass, etc.) ), Forest trees (beans, beans, pine, hiba, cedar, cypress, etc.) and ornamental plants (herbs and flowers such as kiku, roses, carnations, orchids, garden trees such as ginkgo, cherry blossoms, aoki, etc.) It can also be used to control arthropods, soft animals, nematodes, and fungi such as fungi, deformed fungi, fungi, and exsanguins, as well as harmful organisms such as bacteria. .. Specific pests include the
  • Lepidoptera of the phylum Arthropod for example, Cossidae Helicoverpa armigera, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Tricho ), Yotoga (Mamestra brassicae), Shiroichimojiyoto (Spodoptera exigua), Hasmonyoto (Spodoptera litura), etc., Suga family Konaga (Plutella xylostella), Hamakiga family apple cossidae (Adoxophyes) honmai), Midarekakumonhamaki (Archips fuscocupreanus), Chahamaki (Homona magnanima), Chanohosoga (Caloptilia theivora), Nashihimeshinkui (Grapholita molesta), etc., Chaminoga (Eumeta minuscula), etc.
  • Iraga family Iraga (Monemaflavecens), Hirohelia oila (Parasa lepida), Himekuroiraga (Scopelodes con) Tracus, etc., Crambi suppressalis, Scirpophaga incertulas, Cnaphalocrocis medinalis, Helulla undalis, Conogethes punctiferis, Conogethes punctiferlis, etc. Shibatuga (Parapediasia teterrella), etc., Tosakaftomeiga (Locastra muscosalis), etc.
  • Ichimonjiseri (Parnara guttata) of the family Lappet moth, Namiageha (Papilio xuthus) of the swallowtail family, Piieris rapae crucivora, etc. of the white butterfly family, Uranamishijimi (Lampides boeticus), etc. Etc., Convolvulus hawk (Agrius convolvuli), etc., Monkuroshachihoko (Phalera flavescens), etc., Lappet moth family, Obikareha (Malacosoma neusttrium testaceum), etc., Yamamayuga family, Kussan (Saturnia japonica), etc.
  • Coleoptera for example, Coleoptera (Anomala cuprea), Chrysomelidae (Popillia japonica), Oxycetonia jucunda, Chrysomelidae (Anomala geniculata), etc., jewel beetle (Anomala geniculata), etc.
  • 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
  • Homoptera of the order Hemiptera for example, the whitefly (Platypleura kaempferi), the whitefly family Homoptera (Arboridia apicalis), the whitefly (Empoasca onukii), the whitefly (Empoasca onukii), the whitefly (Platypleura kaempferi), etc.
  • Whitefly Homoptera Nephotettix virescens
  • Delphacidae Himetobiunka Laodelphax striatellus
  • Tobiirounka Naparvata lugens
  • Sejirounka Sogatella furcifera
  • Psyllidae Sogatella furcifera
  • Psyllidae Psyllidae
  • Psyllidae Various biotypes of whitefly (Diaphorina citri), Delphacidae whitefly (Aleurocanthus spiniferus), silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), whitefly, whitefly (Dialeurodesci), etc.
  • Psyllidae whitefly Viteus vitifolii
  • Aphids Pseudococcus comstocki
  • Aphids Phenacoccus viburnae
  • Fujikonakaigaram Phenacoccus kraunhiae
  • Aphids of the family Aphids Ceroplastes ceriferus
  • Aphids Ceroplastes ceriferus
  • Onidiell Adults, larvae and eggs such as a aurantii
  • San Jose scale Comstockaspis perniciosa
  • Pseudaulacaspis pentagoa Pseudaulacaspis pentagoa
  • Thrips Thysanoptera
  • Thrips palmi Karny Scirtothrips dorsalis
  • Thrips palmi Thrips palmi
  • Negia thrips Thrips tabaci
  • Thrips tabaci Thrips tabaci
  • Thrips thrips Thrips palmi Karny (Frankliniella occidentalis)
  • Thrips palmi Karny Heliothrips haemorrhoidalis
  • Thrips palmi Karny Pierothrips diospyrosi
  • Thrips palmi Karny Haplothrips
  • Hymenoptera for example, Tenthredinidae (Athalia rosae ruficornis), Churenji bee (Arge pagana), Mifushihabachi (Arge mali), etc., Formica japonica (Dryocsmus kuriphilus) Adults such as the leaf-cutting bees (Megachile nipponica nipponica), Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Fire ant (Solenopsis richteri, S. invicta, S.
  • Agromyzidae for example, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Rhacochlaena japonica, Bactrocera cucurbitae, etc., Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae, Agromyzidae (Drosophila suzukii), etc., Agromyzidae (Liriomyza trifolii), Tomato leafminer (Liriomyza sativae), Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae), Agromyzidae (Agromyza oryzae) Adults, larvae and eggs such as leaf
  • Orthoptera for example, Migratory locust (Locusta migratoria), Ruspolia lineosa (Ruspolia lineosa), Teleogryllus emma (Teleogryllus emma), Oxya yezoensis (Truljalia hibinonis), etc.
  • Etc. adults, larvae and eggs such as Oxya yezoensis of the Orthoptera family; Adults, larvae and eggs of the order Termites (Isoptera), such as the termites Odontotermes formosanus of the family Termites; Adults, larvae and eggs of the order Earwig (Dermaptera), such as the earwig (Labidura riparia) of the family Earwigidae;
  • Primitive string tongues of the molluscs Gastropods such as Pulmonata, such as Pomacea canaliculata of the family Tanishimodoki, Pulmonata, such as Achatina fulica of the family Acusta despectarum Namekuji (Meghimatium bilineatum), Niwakouranamekuji (Milax gagates), Keelback slug (Lehmannina valentiana), Giant African snail (Acusta despecta sieboldiana), etc.
  • Pulmonata such as Pomacea canaliculata of the family Tanishimodoki
  • Pulmonata such as Achatina fulica of the family Acusta despectarum Namekuji (Meghimatium bilineatum), Niwakouranamekuji (Milax gagates), Keelback slug (Lehmannina valentiana), Giant African snail (Acusta despecta sieboldiana), etc.
  • Tylenchida of the phylum phylum for example, Ditylenchus destructor of the Anguina family, Tylenchorhynchus claytoni of the Tylenchorhynchus, etc., Pratylenchus of the Platylencus family.
  • Pratylenchus coffeae, etc. Helicotylenchus dihystera, etc., Heterodera rostochiensis, Globodera rostochiensis, etc., Meloid Guinea family Nematodes (Criconema jaejuense), etc., Strawberry nematodes (Nothotylenchus acris), etc., Aphelecchoides fragarriae, etc .; Aphelecchoides fragarriae, etc .; .), Yumihari nematode (Trichodorus sp.), Etc.
  • Trichodolus 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 can be applied include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), and internal scab (Pantoea ananatis). ), Brown streak disease (Acidovorax avene subsp. Avenae), leaf sheath browning disease (Pseudomonas fuscovaginae), white leaf blight (Xanthomonas oryzae pv.
  • Nuda Namagusa black spike disease (Tilletia caries), eye print disease (Pseudocercosporella herpotrichoides), cloud-shaped disease (Rhynchosporium secalis), leaf blight (Septoria tritici), blight (Leptosphaeria nodorum), net spot disease (Pyrenophora) , Hyomon disease (Helminthosporium zonatum Ikata), black scab (Pseudomonas syringae pv.
  • citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum) , Brown rot (Phytophthora citrophthora ,, P. Nicotianae), scab (Phyllosticta citricarpa), etc .
  • Alternaria mali scab (Venturia inaequalis), scab (M) ycospherella pomi), Colletotrichum acutatum, Botryosphaeria berengeriana, Gymnosporangium yamadae, Monilinia fructicola, etc .
  • citrus black spot disease Diaporthe citri
  • scab Elsinoe fawcetti
  • fruit rot Penicillium digitatum
  • Brown rot Brown rot
  • scab Phyllosticta cit
  • brown spot disease Phomopsis vexans
  • udonko disease Erysiphe cichoracearum
  • black spot disease Alternaria japonica
  • white spot disease of abrana family vegetables Cercosporella brassicae
  • Soft rot Pectobacterium carotovorum subsp. Carotovorum
  • Kyabetsu rot Pseudomonas syringae pv. Marginalis
  • Black rot Xanthomonas campestris pv. Campestris
  • Lettuce rot Psudomonas campestris pv.
  • Campestris , Spot bacterial disease (Xanthomonas campestris pv. Vitians) Negi rust (Puccinia allii), etc .; Soybean purple spot disease (Cercospora kikuchii), Black spot disease (Elsinoe glycines), Black spot disease (Diaporthe phaseolorum var. Sojae), etc.
  • Tobacco red spot disease (Alternaria longipes), pythium disease (Erysiphe cichoracearum), charcoal disease (Colletotrichum tabacum), sticky disease (Peronospora tabacina), plague (Phytophthora nicotianae), wilt disease (Ralstonia solanacearum) Pectobacterium carotovorum subsp. Carotovorum, etc .; Cercospora beticola, Aphanomyces cochliodes, etc .; Rose scab (Diplocarpon rosae), Udonko disease (Sphaerotheca pannosa), etc.
  • Botrytis cinerea of various crops such as eggplant, cucumber and lettuce, mycorrhizal disease ( Sclerotinia sclerotiorum; turf snow rot (Pythium iwayamai, Tyohula incarnate, Fusarium nivale, Sclerotinia borealis), Udonko disease (Erysiphe graminis), Farrying disease (Lycoperdon perlatum, Lepista) (Ceratobasidium spp.), Bacterial wilt (Gaemannomyces graminis), Curvularia geniculata, Leaf rot (Rhizoctonia solani), Pythium periplocum, Pythium vanterpoolii, Puccinia sp. Spot disease (Septoria chrysanthemi-indici), white rust (Puccinia horiana), root cancer (Agrobacterium tumefaciens), etc .; Botry
  • the compound of the present invention operates indoors in buildings including ordinary houses, and damages or rots wood and its processed products such as wooden furniture, stored foods, clothing, books, etc., and damages our lives. It can also be used to control arthropods and fungi. Specific pests include the following.
  • Termites of the phylum Termites such as termites of the family Termites (Coptotermes formosanus), Yamato termites (Reticulitermes speratus), and other termites of the genus Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), American termites (Incisitermes minor), termites (Odontotermes formosanus), termites Hodotermopsis jzponica, termites and termites (Cryptotermes domesticus).
  • termites of the family Termites such as termites of the family Termites (Coptotermes formosanus), Yamato termites (Reticulitermes speratus), and other termites of the genus Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.
  • American termites
  • Maize weevil for example, Maize weevil (Sitophilus zeamais), Maize weevil (Sitophilus zeamais), Maize weevil (Callosobruchus chinensis), Pea weevil (Bruchus pisorum), Pea weevil (Bruchus pisorum) Maize weevil (Tribolium castaneum), Maize weevil (Tribolium confusum), etc., Maize weevil (Oryzaephilus surinamensis), Skin beetle (Cryptolestes pusillus), Cryptolestes pusillus, Maize weevil, La weevil (Stegobium paniceum), etc., Maize weevil (Attagenus unicolor japonicus), Himemaru weevil (Anthrenus verbasci), Harajiro weevil (Dermestes maculatus), etc., Maize weevil, Maize weevil, etc. Adults, larva
  • Chowidae for example, Spodoptera frugiperda (Cadra cautella), Spodoptera frugiperda (Ephestia kuehniella), Indianmeal moth (Plodia interpunctella), Angoumois grain moth (Sitotroga cerealella) Adults, larvae and eggs of translucens, Tineola bisselliella, etc .; Adults, larvae and eggs of the order Moth, for example, Lepinotus reticulatus of the family Snout moth, Liposcelis bostrychophilus.
  • 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 Acaridae
  • Tyromyces palustris, Coriolus versicolor, etc. which are wood-rotting fungi of fungi
  • Deterioration of materials Microorganisms such as Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cla
  • the compound of the present invention can also be used to control harmful organisms that damage or weaken trees in natural forests, planted forests and urban green areas.
  • 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) Lackey moth (Malacosoma neustria testacea), Matsukareha (Dendrolimus spectabilis), Tsuga kareha (Dendrolimus superans), etc., Meiga family Crytoblabes loxiella, etc., Yaga family longhorn beetle (Agrotis se) (Ptycholoma lecheana circumclusana), Kurimiga (Cydia kurokoi), Sugikasaga (Cydia cryptomeriae), etc., Hitrigger family, Spilosoma imparilis, American white-spotted beetle (Hyphantria
  • Hemiptera for example, Cinara todocola of the Aphididae family, Adelges japonicus of the Aphididae family, Diaspididae Sugimarukaigaramushi (Aspidiotus cryptomeriae), etc.
  • the compounds of the present invention are arthropods that parasitize vertebrates, especially warm-blooded vertebrates such as cows, sheep, goats, horses, pigs, poultry, dogs, cats and fish, internally or externally. It can also be used to prevent, treat or control animals, nematodes, trematodes, vertebrates and protozoa.
  • the target animal species include rodents such as mice, rats, hamsters and squirrels, carnivores such as ferrets, pets and experimental animals of birds such as ducks and pigeons. Specific pests include the following.
  • Flies of the phylum Psychodidae such as Yamatoab (Tabanus rufidens), Akaushiab (Tabanus chrysurus), Blowfly (Musca bezzii), Psychodidae (Musca domestica), Stomoxys calcitrans, etc.
  • Ceratopogonidae (Gasterophilus intestinalis), Ceratopogonidae (Hypoderma bovis), Botfly (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), Kogataakaieka (Culex pipiens triaeniorhynchus summorosus), Botfly (Ades albopictus), etc.
  • Lice for example, lice (Haematopinidae suis), lice (Haematopinidae eurysternus), lice (Damalinia bovis), lice, lice, lice, lice Adults, larvae and eggs such as (Menopon gallinae); Dermanyssus gallinus (Arachnid), for example, Dermanyssus gallinus (Varroa jacobsoni), Ixodidae Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Takasagokirama testudinarium), etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Arachnid, Demodex phylloides, etc.
  • elegans for example, Bunostomum pheasum, Pig kidney, 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 .
  • Amoeba eyes of the fleshy class such as Entamoeba
  • Piroplasma subclasses of the parasitic protozoa such as Theilaria, Babesia, etc.
  • Late parasitic subclasses such as Eimeria, Plasmadium, Toxoplasma, etc.
  • the compound of the present invention can also be used to exterminate harmful organisms that cause direct harm or discomfort to the human body, or to maintain public health conditions for harmful organisms that carry or mediate pathogens.
  • Specific pests include the following.
  • Lepidoptera of the phylum Arthropod for example, Yellow-tail (Sphrageidus similis) of the family Dokuga, Kunugia undans of the family Kaleha, Parasa consocia of the family Iraga, Artona martini (Artona martini) Adults, larvae and eggs; 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 such as Vespa simillima xanthoptera of the Vespidaceae family, Brachyponera chinensis of the Ant family, and Batozonellus annulatus of the Spider wasp family; Flies, for example, Blowfly (Armigeres subalbatus), Ceratopogonidae (Culicoides nipponensis), Chironomus yoshimatsui, etc., Chironomus yoshimatsui, Simulium nikkoense, etc.
  • Blowfly Armigeres subalbatus
  • Ceratopogonidae Culicoides nipponensis
  • Chironomus yoshimatsui etc.
  • Chironomus yoshimatsui Simulium nikkoense, etc.
  • Ceratopogonidae Hirosia humilis
  • Ceratopogonidae Musca domestica
  • Ceratopogonidae Feannia canicularis
  • Blowfly Phormia regina
  • Ceratopogonidae Sarcophaga peregna
  • Ventricosus etc., Demodex folliculorum, Demodex folliculorum, Dermotophagoides pteronyssinus, Sarcoptes scabiei, Arachnid, Trombicula akamushi, etc. ;
  • Authentic spiders such as the jumping spider (Chiracanthium japonicum), the jumping spider (Heteropoda venatoria), the spider spider (Spermophora senoculata), the spider (Pholcus ), Etc.
  • the compounds of the present invention are of particular value in controlling pests such as arthropods, gastropods, nematodes and fungi that damage agricultural crops, natural forests, plantations and trees and ornamental plants in urban green areas. is there.
  • the compounds of the present invention are in their commercially useful formulations and in the forms of use prepared by those formulations, other active compounds such as pesticides, acaricides, nematodes, fungicides. It can also exist as a mixture with agents, synergists, plant growth regulators, poison bait or herbicides.
  • Examples of usage include wettable powders, granule wettable powders, dry flowable agents, water solvents, emulsions, liquids, oils, flowable agents such as suspensions in water and emulsions in water, 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.
  • anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine.
  • 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 compound of the present invention may be blended as an active ingredient by one kind or a combination of two or more kinds.
  • 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 plants is usually located in areas where damage is occurring or may occur due to these pests.
  • all layers of soil, arthropod application, floor soil mixture, cell seedling treatment, planting hole treatment, plant root 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 hydroponic cultivation, smoking or tree trunk injection.
  • the amount of active ingredient per 10 ares is generally 0.1 to 1000 g, preferably 1 to 100 g, although it varies depending on the type and amount of harmful organisms, the type of target crop / tree, cultivation form, and growing condition.
  • the crops or the like may be treated in the state of the preparation.
  • the preparation is not diluted or diluted with water.
  • a method of applying to a plant stock or a nursery for raising seedlings a method of spraying granules on a plant stock or a nursery for raising seedlings, a powder, a wettable powder, and granulated water before sowing or transplanting.
  • Wettable powders, granule wettable powders, aqueous solvents, emulsions, liquids, 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 hilling 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 preparation can be sprayed or injected into the soil as it is or mixed 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.
  • Examples of the seed treatment method include diluting a liquid or solid preparation or immersing the seed in a liquid state without diluting it to allow the drug to adhere and permeate, and mixing the solid preparation or the liquid preparation with the seed.
  • 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" for which the seed treatment is performed means a plant body in the early stage of cultivation used for plant reproduction, 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 in the case of application 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 earth, 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. It is also preferable to treat the granules in the planting holes at the time of planting or to mix them with a cultivation carrier near the transplanting site.
  • the compounds of the present invention are also valuable in protecting wood (standing trees, fallen trees, processed wood, stored wood or structural wood) from damage by insects such as termites or corns and fungi. 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.
  • the oil, emulsion, wettable powder, powder, etc. 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 for oils, powders and granules, emulsions, wettable powders and sols.
  • spray 0.01 to 100 g of the active ingredient compound per 1 m 2 on the soil or wood surface.
  • the compounds of the present invention can be used for lepidoptera, corns, mites and other products when stored as-is, powdered or mixed in products such as cereals, fruits, nuts, spices and tobacco. It can be used to protect against damage from fungi. Also, when storing animal products (skin, hair, wool, feathers, etc.) and plant products (cotton, paper, etc.) in a natural or converted state, from the attack of Lepidoptera, Kochu, stains and cockroaches It can be protected and can be protected from attacks by lepidoptera, cockroaches, flies and mites when storing foods such as meat and fish.
  • compositions such as spraying oils, emulsions, wettable powders, powders, etc., installing resin transpiration agents, treating smoke agents and fumes, installing granules, tablets and poison bait, spraying aerosol, etc.
  • These formulations may 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 compounds of the present invention spread or spread diseases of arthropods and fungi, humans and domestic animals that parasitize the body surface of humans and domestic animals and cause direct harm such as skin feeding or blood sucking. It is valuable for the control or prevention of arthropods, nematodes, trematodes, tapeworms, protozoa, and arthropods that cause discomfort to humans. In such situations, a small amount of the compound of the present invention may be mixed into a meal or feed, or an appropriate orally ingestible compounded drug composition or the like, for example, tablets, pills, containing a pharmaceutically acceptable carrier or coating substance, etc.
  • the active ingredient compound is generally contained in the preparation in an amount of 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass.
  • a device for example, a collar, a medallion, an ear tag, etc.
  • an animal so as to control arthropods locally or systemically can also be used.
  • the present invention is not necessarily limited thereto.
  • the beverage When administered orally as medicated drinking water, the beverage is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with a suspending agent such as bentonite or a wetting agent or other excipient. is there.
  • a suspending agent such as bentonite or a wetting agent or other excipient. is there.
  • Beverages generally also contain an antifoaming agent. Beverage formulations generally contain 0.01-1.0% by weight, preferably 0.01-0.1% by weight, of the active ingredient compound.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually used. These uses are made by homogeneously mixing the active ingredient with appropriately finely ground diluents, fillers, disintegrants and / or binders such as starch, lactose, talc, magnesium stearate, vegetable rubber and the like. Manufactured.
  • Such unit-use formulations can vary widely in mass and content of 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 is used as an insecticide for arthropods that cause direct harm or arthropods that are vectors of diseases, and is an oil agent for the surrounding environment in which those harmful organisms may be latent. , Emulsion, wettable powder, etc. spraying / injection / irrigation / coating, powdering agent, fumigant, mosquito repellent incense, self-burning smoke agent, chemical reaction type smoke agent, etc.
  • 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 mass.
  • the compound of the present invention 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, fluvalinate, furamethrin, halophen Prox (halfenprox), imiprothrin (imiprothrin) permethrin (permethrin), phenothrin (phenothrin), prallethrin (prallethrin), pyrethrin (pyrethrins), resmethrin (resmethrin), silafluofen (silafluofen), tefluthrin (tefluthrin), tefluthrin (tefluth
  • Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc .
  • Diamide agents such as chlorantraniliprole, cyantraniliprole, cycloaniliprole, flubenziamid, tetraniliprole, etc .
  • Phenylpyrazole agents such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore, etc .;
  • Neristoxin agents such as bensultap, cartap, thiocyclam, thiosultap, etc .
  • Insect growth regulators such as phenylbenzoylurea and diacylhydrazines, such as chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novallon. (Novaluron), teflubenzuron (teflubenzuron), triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.
  • Juvenile hormones such as diofenolan, fenoxycarb, hydroprene, metoprene, pyriproxyfen, etc .;
  • Insecticides produced by microorganisms such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin. , Polyoxin complex (polioxin), spinetram (spinetram), spinosad (spinosad), BT agent, etc.; Insecticide derived from natural substances, such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxy propyl ester, soybean lecithin, nicotine.
  • Insecticide derived from natural substances such as anabasine, azadiractin, deguelin, fatty acid glyceride (decanolyoctanoylglycerol), hydroxy propyl 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 .;
  • pesticides include, for example, afidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz. ), DBEDC (Dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), Flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, flupyrimin, fluralanel, fluralaner fluxametamide), hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotine sulfate, oxazosulfyl, Pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, triflumezopyrim
  • Acaricides such as acequinocyl, acynonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromo. Rate (bromopropylate), quinomethionat, clofentezine, cyenopyrafen, cyflumetofen, tricyclohexatin hydroxide (cyhexatin), dicofol (dicofol), dienochlor, ethoxazole , Fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, hexythiazox, pyrimidifen, pirimidifen Propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spi
  • Nematode killing agents such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, fusthiazate. furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, moranteltartarate, oxamyl, thioxazafen, etc. ; Poisonous baits such as chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin and the like can be mentioned.
  • the compound of the present invention can also exist as a mixture with an active compound other than a compound having pest control activity, mite control activity or nematode control activity.
  • an active compound other than a compound having pest control activity, mite control activity or nematode control activity.
  • a compound having bactericidal activity, herbicidal activity or plant growth regulator activity it is possible to reduce the control labor and the amount of drug.
  • Synergistic effects 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, lime sulfur, captan captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole, chlorofenazole, chloropicrin, chlorothalonil , Chlozolinate, DBEDC (complex of bis (ethylenediamine) copper-bis- (dodecy
  • Fluquinconazole flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonyl (Fludioxonil), flusilazole, flutianil, flutriafol, furametpyr, furametpyr, furconazole, guazatine, hexaconazole, hydroxyioxazole , Hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine acetate, iminoctadine Albesilate (iminoctadine-DBS), imponoctadine-DBS (Iprobenfos), iprodione, iprovalicarb, isofetamid, isoprothiolane, isopyrazam, isotianil, kasugamycin, cresoxim-methyl mancozeb), mand
  • Aclonifen As a compound having herbicidal activity, for example, Aclonifen, acifluofen-sodium, alachlor, alloxydim, amicabazone, amidosulfuron, anilofos, ashlam, atrazine (aclonifen) atrazine), azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzofenap, bialaphos ), Bifenox, Bromoxynil, Bromoxynil, butamifos, cafenstrole, calcium peroxide, carbetamide, cinosulfuron, clomeprop, clomeprop Cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclohop-methyl, diflufenican,
  • Aclonifen acifluofen-sodium, alachlor, alloxy
  • Mefenacet mesosulfuron, metamitron, metabenzthiazuron, metosulam, metribuzin, napropamide, neburon, oxadiargyl (Oxadiazon), oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor, propoxycarbazone, prosulfocarbazone, prosulfocarbazone (oxadiazon), oxaziclomefone (oxaziclomefone), paraquat (paraquat), pendimethalin (pendimethalin), pentoxazone (pentoxazone), phenmedipham (phenmedipham), pretilachlor (pretilachlor), propoxycarbazone.
  • Colytic agents such as methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide, phenyl salioxon, piperonil 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 (GV), nuclear polyhedrosis virus (CPV), and nuclear polyhedrosis virus (CPV).
  • cytoplasmic polyhedrosis virus CPV
  • insect poxvirus EPV
  • GV granulosis virus
  • GV nuclear polyhedrosis virus
  • CPV nuclear polyhedrosis virus
  • CPV nuclear polyhedrosis virus
  • CPV nuclear polyhedrosis virus
  • Viral preparations such as Nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monocrosporium phymatophagum, Pekilomyces phymatophagum, Pekilomyces fumosolopes transpemoriaces ), Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc.
  • NPV Nuclear polyhedrosis virus
  • Beauveria bassiana Beauveria brongniartii
  • Monocrosporium phymatophagum Monocrosporium phymatophagum
  • Pekilomyces phymatophagum Pekilomyces fumosolopes transpemoriaces
  • Steinernema carpocapsae Steinernema glaseri
  • Steinernema kushidai Verticillium lecanii
  • Micropesticide Agrobacterium radiobactor, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma atroviride, Trichoderma lignolan pesticides used as pesticides -Similar effects can be expected by mixing with biopesticides used as herbicides such as Campestris (Xanthomonas campestris).
  • biopesticides used as herbicides such as Campestris (Xanthomonas campestris).
  • biological pesticides for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani, Aphidius colemani (Chrysoperia carnea), Hamoglycomayu bee (Dacnusa sibirica), Isaea Himekobachi (Diglyphus isaea), Onshitsutsuyakobachi (Encarsia formosa), Sabakutsuyakobachi (Eretmocerus eremicus), Arigatashima thrips (Franklyseius) , Kanmurihimekobachi (Hemiptarsenus varicornis), Hamogurimidorihimekobachi (Neochrysocharis formosa
  • Example 1.2 Synthesis of 1,4-dimethyl-1- (1,1,1-trifluoroethyl) thiobenzene
  • a solution of 2,4-dimethylbenzenethiol (14.7 mL) in DMF (200 mL) is cooled in an ice bath.
  • potassium carbonate (18.3 g) and benzene (5.17 g) were added.
  • 2,2,2-trifluoroethyl iodide (25.1 g) was added dropwise over 25 minutes, and the mixture was stirred in an ice bath for 3 hours and the reaction solution was heated to room temperature for 22 hours.
  • the reaction was poured into ice water and extracted 3 times with hexane.
  • Example 2.2 Synthesis of 2,4-dimethyl-5-[(1,1,1-trifluoroethyl) thio] benzaldehyde 2,4-dimethyl-1- (1,1) in a 3-diameter flask equipped with a dropping funnel. , 1-Trifluoroethyl) Thiobenzene (10.0 g) was added, and the inside of the container was replaced with argon. To this, 100 mL of dry dichloromethane was added, and the mixture was cooled in an ice bath. In response, 100 mL of titanium tetrachloride (1.0 M dichloromethane solution) was added dropwise over 3 hours.
  • Example 5 Synthesis of (2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl) thio) phenyl) methanol (2-fluoro-4-methyl-5-((2,2,2-tri) Sodium tetrahydroborate (174 mg) was added to a 13 mL solution of fluoroethyl) thio) benzaldehyde (957 mg) in ethanol at room temperature, and the mixture was stirred for 30 minutes. Then, ethyl acetate, water, and 1N hydrochloric acid were added in that order, and ethyl acetate was added. The combined organic layers were washed with saturated brine and dried over sodium sulfate.
  • Emulsion Compound of the present invention (10 parts), N-methyl-2-pyrrolidone (reagent) (10 parts), xylene (reagent) (70 parts), New Calgen D-230 (polyoxyethylene castor oil, Takemoto oil and fat) Co., Ltd.) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.
  • Formulation Example 4 Microemulsion
  • the compound of the present invention (10 parts), xylene (reagent) (20 parts), Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (20 parts), Airroll CT-1L (Dioctyl) Sodium sulfosuccinate, Toho Chemical Industry Co., Ltd. (2.0 parts) and water (48 parts) were uniformly mixed to obtain a microemulsion.
  • Formulation Example 5 Water Solvent
  • the compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzene sulfonate, Toho Chemical Industry Co., Ltd.) (3 parts) and sodium hydrogen carbonate (reagent) (82 parts) were uniformly mixed. Later, it was pulverized using a fine pulverizer to obtain an aqueous solvent.
  • Preparation Example 6 Liquid -1
  • the compound of the present invention (20 parts), N-methyl-2-pyrrolidone (reagent) (70 parts) and Neucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil & Fat Co., Ltd.) (10 parts) are uniformly mixed and dissolved. The solution was obtained.
  • Formulation Example 8 Wettable Compound (20 parts), Toxil GU-N (White Carbon, Oriental Silicon Corporation) (20 parts), Solpol 5096 (Polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.) ( 10 parts) and SS clay (clay, Showa KDE Co., Ltd.) (50 parts) were mixed and then pulverized using a fine pulverizer to obtain a wettable powder.
  • Solpol 5096 Polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.
  • SS clay clay, Showa KDE Co., Ltd.
  • Formulation Example 9 Granule wettable powder
  • the compound of the present invention (50 parts), Sun Extract P252 (sodium lignin sulfonate, Nippon Paper Industries, Ltd.) (5 parts), and SS clay (clay, Showa KDE Co., Ltd.) (45 parts).
  • Sun Extract P252 sodium lignin sulfonate, Nippon Paper Industries, Ltd.
  • SS clay clay, Showa KDE Co., Ltd.
  • Formulation Example 10 Slurry agent The compound of the present invention (20 parts), Solpol 7948 (polyoxyalkylene tristyrylphenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water. (40 parts) was mixed in advance and wet-pulverized with a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was well mixed and dispersed in water (24.8 parts) to prepare a gel-like product, which was thoroughly mixed with the crushed slurry to prepare a flowable agent. Obtained.
  • Fine Granules-1 The compound (2 parts) of the present invention was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 4 (98 parts) using a rolling granulator, and dried to obtain a fine granule.
  • Fine Granules-2 The compound of the present invention (5 parts) and Toxile GU-N (5 parts) were mixed, pulverized using a fine pulverizer, and uniformly mixed with Iide silica sand (quartz sand, JFE Mineral Co., Ltd.) (80 parts). Toxanone GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) was further mixed with this mixture while spraying a diluted aqueous solution to obtain a granular composition. The granular composition was dried to obtain a fine granule.
  • Toxanone GR-31A polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.
  • Formulation Example 15 Powdering agent After uniformly mixing the compound of the present invention (5 parts), Toxil GU-N (5 parts) and Omori fine powder clay (clay, Omori Sangyo Co., Ltd.) (90 parts), use a pulverizer. And crushed to obtain a powder.
  • Comparative Agent A 13-24 described in US 2009/0082389 A1
  • Test Example 1 A 430 ml capacity polyethylene cup containing test water for killing imago against Tetranychus urticae Koch was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from the primary leaves of the common bean were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs.
  • This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C. Four days after the treatment, the life and death of the adults and the agony were investigated under the binocular, and the insecticidal rate (%) was determined by killing the agony insects. The test was carried out by using 1 cup in each section.
  • Insecticidal rate (%) (number of dead larvae / number of test larvae) x 100
  • compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6 , C-7, D-1, D-2, D-3, D-4 of the present invention showed 100% insecticidal rate.
  • Comparative Agent A had an insecticidal rate of 0%.
  • Test Example 2 Density suppression test against Tetranychus urticae Koch A 430 ml capacity polyethylene cup containing test water was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, two leaf discs (2 cm x 5 cm) made from the primary leaves of the common bean were placed on absorbent cotton so that the water in the cup was constantly replenished, and 10 adult female spider mites were placed on the leaf discs.
  • 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-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-2, C-3, C-4, C-5, C-6, C-7 , D-1, D-2, D-3, D-4 of the present invention showed a density suppression rate of 100%.
  • Comparative Agent A had a density suppression rate of 0%.
  • Test Example 3 A polyethylene cup having a capacity of 430 ml containing test water for killing imagoes against Panonychus citri McGregor was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper.
  • Insecticidal rate (%) (number of dead larvae / number of test larvae) x 100
  • compound numbers A-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-10, A-11, A-13, A -14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6, C-7 , D-1, D-3 of the present invention compound showed 100% insecticidal rate.
  • Comparative Agent A had an insecticidal rate of 0%.
  • Test Example 4 Density suppression test against Panonychus citri McGregor A 430 ml capacity polyethylene cup containing test water was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper.
  • Next-generation density suppression effect on eggs laid by adults 7 days after 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 by using 1 cup in 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-1, A-2, A-3, A-4, A-5, A-6, A-7, A-8, A-9, A-10, A-11, A -13, A-14, A-15, A-16, B-1, B-2, B-3, C-1, C-2, C-3, C-4, C-5, C-6 , C-7, D-1, D-3, D-4 of the present invention showed a density suppression rate of 100%.
  • Comparative Agent A had a density suppression rate of 0%.
  • Test Example 5 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 styrol cup (9 cm in diameter and 6.5 cm in height). , 50 ml of water diluted solution (100 ppm) of the emulsion prepared according to Preparation Example 1 was irrigated, and then tomatoes were sown (13 grains / 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 bump index of treated plot / Root bump index of untreated plot)] x 100
  • Comparative Agent A had a control value of 0%.
  • Test Example 6 A 430 ml capacity polyethylene cup containing test water for killing larvae against Bemisia tabaci (Biotype-B) was covered with a lid having a hole (diameter about 5 mm) in the center. Make a notch with a width of about 5 mm in a circular filter paper with a diameter of 6.5 cm so that a strip-shaped filter paper piece is formed, and immerse the strip-shaped filter paper piece hanging downward from the hole in the lid into the water in the cup. And put cotton wool on the filter paper. In this way, three leaf discs (2 cm x 2 cm) cut out from the primary leaves of the common bean to lay eggs on cotton wool that is constantly replenished with water in the cup so that the number of eggs per disc is about 10 are placed.
  • Spawning was carried out by holding pot-planted common beans in a greenhouse where Bemisia tabaci is occurring for 24 hours.
  • This cup was placed in an acrylic cylinder having a height of 50 cm and a diameter of 10 cm, and a water-diluted solution (500 ppm) of an emulsion prepared according to Formulation Example 1 was sprayed at 2.0 ml per cup using an airbrush. After spraying, it was kept in a constant temperature room at 25 ° C.
  • the number of unhatched eggs and the state of the hatched larvae were observed under binoculars in three categories: survival, agony (non-walkable state), and death. Based on the observation results, the egg killing + larval rate (%) was calculated.
  • Egg killing + larva rate (%) (number of unhatched eggs + number of abnormal larvae + number of dead larvae) / number of test eggs x 100
  • compound numbers A-3, A-6, C-2, C-7, C-8, C-9, C-12, C-14, C-15, C-16, D-1, D The compound of the present invention of -3 showed an egg killing + larval rate of 90% or more.
  • Comparative Agent A had an egg killing rate of 0% and a larval rate.

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Abstract

L'invention concerne un agent agricole et horticole, en particulier un composé étant utile en tant que principe actif d'un agent antiparasitaire agricole et horticole, d'un agent de lutte contre les acariens, d'un agent de lutte contre les nématodes ou d'un agent de lutte contre les maladies. L'invention concerne un dérivé de 1-benzylamine représenté par la formule (1) ou (2) un N-oxyde de celui-ci, ou un sel de celui-ci.　Dans la formule, R1 est, par exemple, un groupe alkyle en C1-6 ou un groupe halo-alkyle en C1-6, n est 1, X est, par exemple, un groupe alkyle en C1-6, un groupe halo-alkyle en C1-6, un atome d'halogène ou un groupe cyano, R2a, R2b, R2c et R2d sont, par exemple, des atomes d'hydrogène, J1 et J2 sont des liaisons directes ou des groupes alkylène, M sont des groupes alkylène ou -NR5-, -O-, -S-, -S(O)-, ou -S(O)2-, R5 est, par exemple, un groupe alkyle en C1-6 ou similaire, R6 et R7 sont, par exemple, des atomes d'hydrogène ou des groupes alkyle en C1-6.
PCT/JP2020/023191 2019-06-13 2020-06-12 Nouveau dérivé de 1-benzylamine et agents agricoles et horticoles l'utilisant comme principe actif Ceased WO2020251012A1 (fr)

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