WO2022255465A1 - Composé de benzimidazole ou sel associé, insecticide/acaricide agricole et horticole et agent de lutte contre la filariose canine pour animaux le contenant, et son procédé d'utilisation - Google Patents

Composé de benzimidazole ou sel associé, insecticide/acaricide agricole et horticole et agent de lutte contre la filariose canine pour animaux le contenant, et son procédé d'utilisation Download PDF

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WO2022255465A1
WO2022255465A1 PCT/JP2022/022543 JP2022022543W WO2022255465A1 WO 2022255465 A1 WO2022255465 A1 WO 2022255465A1 JP 2022022543 W JP2022022543 W JP 2022022543W WO 2022255465 A1 WO2022255465 A1 WO 2022255465A1
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group
strain
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benzimidazole compound
salt
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彰人 渡邊
綾介 田中
遼 崎田
鈴風 石倉
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日本農薬株式会社
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/02—Acaricides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P7/00—Arthropodicides
    • A01P7/04—Insecticides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/695—Silicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Definitions

  • the present invention relates to a benzimidazole compound or a salt thereof, an agricultural and horticultural insecticide and acaricide containing the compound as an active ingredient, a dog heartworm control agent for animals, and a method for using the same.
  • Patent Documents 1 to 4 show that certain benzimidazole compounds are useful as insecticides, medicines, etc.
  • Patent Documents 1 to 4 do not describe a benzimidazole compound having an alkylsulfonyl group or the like at the 1-position and a nitrogen atom of a pyrazole ring bonded to the 2-position and its insecticidal effect.
  • Crop production such as agriculture and horticulture is still heavily damaged by pests, and from the viewpoint of the occurrence of pests that are resistant to existing drugs, the impact on environmental organisms, and labor saving, etc., it has a new action and is useful as a natural enemy.
  • melarsomin dihydrochloride is conventionally known as a canine heartworm control agent, and it is also effective against mature (adult) and immature heartworm.
  • heartworm infection can be prevented by macrolide prophylactic drugs, but year-round prevention is recommended regardless of the breeding conditions of animals.
  • Such long-term use in animals raises concerns about the potential development of resistance to existing drugs, and it is active against heartworm and can be used to treat infections caused by it. There is also a need to provide new drugs.
  • a benzimidazole compound represented by the general formula (1) having a pyrazole group bonded to the 2-position via a nitrogen atom and having a specific sulfonyl group at the 1-position Or a salt thereof and a benzimidazole compound or a salt thereof having a pyrazole group at the 2-position bound by a nitrogen atom represented by the general formula (1-1) exhibit excellent control effects against agricultural and horticultural pests or heartworms.
  • the present inventors have found that the above problems can be solved as well as having the above, and have arrived at the present invention.
  • R is (a1) ( C1 - C6 )alkyl group; (a2) ( C3 - C6 )cycloalkyl group; (a3) ( C3 - C6 )cycloalkyl( C1 - C6 )alkyl (a4) a halo( C1 - C6 )alkyl group; (a5) a ( C2 - C6 )alkenyl group; or (a6) a ( C2 - C6 )alkynyl group.
  • Y 1 , Y 2 , Y 3 and Y 4 may be the same or different and are (b1) a hydrogen atom; (b2) a halogen atom; (b3) a (C 1 -C 6 ) alkyl group; or (b4) a halo (C 1 -C 6 ) alkyl group;
  • X may be the same or different, (c1) hydrogen atom; (c2) ( C1 - C6 ) alkyl group; (c3) cyano ( C1 - C6 ) alkoxy group; (c4) trimethylsilyl ( C1 ( c5 ) (C3-C6) cycloalkyl group; (c6) (C2-C6) alkenyl group; (c7) (C2-C6 ) alkynyl group ; ( c8) ( C1 - C6 )alkoxy; (c9) halo( C1 - C6 )alkyl; (c10) halo( C1 - C6
  • R is (a1) (C 1 -C 6 ) alkyl group; or (a5) (C 2 -C 6 ) alkenyl group; Y 1 , Y 2 , Y 3 and Y 4 are (b1) hydrogen atoms; (c1) a hydrogen atom; (c2) a ( C1 - C6 ) alkyl group; (c3) a cyano( C1 - C6 ) alkoxy group; (c4) a trimethylsilyl ( C1 ( c8 ) (C1 - C6)alkoxy group; (c9) halo(C1-C6)alkyl group; (c10) halo(C1-C6 ) alkoxy group ; (c12) ) (C 1 -C 6 ) alkoxycarbonyl group; (c13) 1,3-dioxan-2-yl group; or (c14
  • a canine heartworm control agent for animals characterized by containing the benzimidazole compound or a salt thereof according to any one of [1] to [2] as an active ingredient
  • the benzimidazole compound having a nitrogen atom of a pyrazole group at the 2-position and a specific sulfonyl group at the 1-position or a salt thereof, and the benzimidazole compound having a nitrogen atom of a pyrazole group at the 2-position of the present invention are for agricultural and horticultural use. It has an excellent effect as an insecticidal acaricide or a heartworm control agent for dogs.
  • halo means "halogen atom” and represents a fluorine atom, chlorine atom, bromine atom or iodine atom.
  • (C 1 -C 6 )alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group , tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group and other linear or branched alkyl groups having 1 to 6 carbon atoms; , "(C 2 -C 6 )alkenyl group” means, for example, vinyl group, vinyl
  • (C 3 -C 8 )cycloalkyl group means a cyclic alkyl group having 3 to 8 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc.
  • (C 1 -C 8 ) alkoxy group includes, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normalhexyloxy group, isohexyloxy group , 1,1,2-trimethylpropyloxy group, normal heptyloxy group, normal octyloxy group and other straight or branched chain alkoxy groups having 1 to 8 carbon atoms.
  • ( C1 - C6 )alkylcarbonyl group includes, for example, acetyl group, propionyl group, butyryl group, isobutyryl group, normal butylcarbonyl group, isobutylcarbonyl group, secondary butylcarbonyl group, tertiary butylcarbonyl group, normal pentyl carbonyl group, isopentylcarbonyl group, tertiary pentylcarbonyl group, neopentylcarbonyl group, 2,3-dimethylpropylcarbonyl group, 1-ethylpropylcarbonyl group, 1-methylbutylcarbonyl group, 2-methylbutylcarbonyl group, normal hexylcarbonyl group, isohexylcarbonyl group, 2-hexylcarbonyl group, 3-hexylcarbonyl group, 2-methylpentylcarbonyl group, 3-methylpentylcarbonyl group, 1,1,2-trimethylpropylcarbon
  • Examples of the "(C 1 -C 6 )alkoxycarbonyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, a normal propoxycarbonyl group, an isopropoxycarbonyl group, a normal butoxycarbonyl group, a secondary butoxycarbonyl group and a tertiary butoxycarbonyl group.
  • normal pentyloxycarbonyl group isopentyloxycarbonyl group, tertiary pentyloxycarbonyl group, neopentyloxycarbonyl group, 2,3-dimethylpropyloxycarbonyl group, 1-ethylpropyloxycarbonyl group, 1-methylbutyloxycarbonyl straight-chain or branched-chain alkoxy group having 1 to 6 carbon atoms such as normal hexyloxycarbonyl group, isohexyloxycarbonyl group, 1,1,2-trimethylpropyloxycarbonyl group, and carbonyl group represents an alkoxycarbonyl group.
  • the "(C 1 -C 6 )alkylene group” includes, for example, a straight or branched chain such as a methylene group, ethylene group, n-propylene group, isopropylene group, n-butylene group, isobutylene group, tert-butylene group and the like. It represents a chain alkylene group having 1 to 6 carbon atoms.
  • the “C 2 -C 6 )alkenylene group” is, for example, a linear or branched alkenylene group having 2 to 6 carbon atoms, such as vinylene group, propenylene group and butenylene group.
  • the “C 2 -C 6 )alkynylene group” includes, for example, linear or branched alkynylene groups having 2 to 6 carbon atoms such as ethynylene, propynylene and butynylene groups.
  • Examples of the "(C 1 -C 6 )alkyleneoxy group” include methyleneoxy, ethyleneoxy, n-propyleneoxy, isopropyleneoxy, n-butyleneoxy, isobutyleneoxy, tert-butyleneoxy represents a straight-chain or branched-chain alkyleneoxy group having 1 to 6 carbon atoms.
  • ( C1 - C6 ) alkyl group "( C2 - C6 ) alkenyl group”, “( C2 - C6 ) alkynyl group”, “(C3 - C6 ) cycloalkyl group”, or
  • the substitutable position of the "(C 1 -C 6 ) alkoxy group” may be substituted with 1 or 2 or more halogen atoms, and when the substituted halogen atoms are 2 or more, the halogen atoms may be the same or different.
  • Halo ( C1 - C6 ) alkyl group can be "Halo ( C1 - C6 ) alkyl group", “Halo ( C2 - C6 ) alkenyl group”, “Halo ( C2 - C6 ) alkynyl group”, “Halo ( C3 - C6 ) cycloalkyl group” or "halo( C1 - C6 )alkoxy group”.
  • Examples of the salts of the benzimidazole compounds represented by the general formulas (1) and (1-1) of the present invention include inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates and fumaric acid. salts, organic acid salts such as maleates, oxalates, methanesulfonates, benzenesulfonates, and paratoluenesulfonates; inorganic or organic bases such as sodium ions, potassium ions, calcium ions, and trimethylammonium; salts can be exemplified.
  • inorganic acid salts such as hydrochlorides, sulfates, nitrates and phosphates, acetates and fumaric acid. salts, organic acid salts such as maleates, oxalates, methanesulfonates, benzenesulfonates, and paratoluenesulfonates
  • the benzimidazole compounds and salts thereof represented by general formula (1) and general formula (1-1) of the present invention have one or more asymmetric centers in their structural formulas, and two or more The present invention includes all optical isomers and mixtures containing them in any ratio. Further, the benzimidazole compounds and salts thereof represented by the general formulas (1) and (1-1) of the present invention have two geometric isomers derived from a carbon-carbon double bond in their structural formulas. may exist, the present invention encompasses all geometric isomers and mixtures thereof in any proportion. Further, the benzimidazole compounds or salts thereof represented by general formula (1) and general formula (1-1) of the present invention may have tautomers in their structural formulas. tautomers and mixtures thereof in any proportion.
  • R is preferably (a1) ( C1 - C6 ) alkyl group; or (a5) ( C2 - C6 ) alkenyl group, Y 1 , Y 2 , Y 3 and Y 4 are preferably (b1) a hydrogen atom; X is preferably the same or different, and is (c1) hydrogen atom; (c2) ( C1 - C6 ) alkyl group; (c3) cyano( C1 - C6 ) alkoxy group; (c4) trimethylsilyl ( ( C1 - C6 )alkoxy group; (c8) ( C1 - C6 )alkoxy group; (c9) halo( C1 - C6 )alkyl group; (c10) halo( C1 - C6 )alkoxy group; (c12) a (C 1 -C 6 ) alkoxycarbonyl group; (c13
  • benzimidazole compounds represented by general formulas (1) and (1-1) of the present invention or salts thereof can be produced, for example, by the following production methods, but the present invention is not limited thereto. do not have.
  • the benzimidazole compound represented by the general formula (1-3) is an inactive benzimidazole compound represented by the general formula (2) and the pyrazole compound represented by the general formula (3). It can be produced by reacting in the presence of a solvent and a base.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride; acetic acid such as sodium acetate and potassium acetate; salts, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide; Nitrogen-containing aromatic compounds such as class amines, pyridine, and dimethylaminopyridine (DMAP) can be mentioned, and the amount used is usually 1 to 10 times the amount of the compound represented by the general formula (3). Used in the molar range.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and sodium hydride
  • acetic acid such as sodium acetate and potassium acetate
  • salts, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxid
  • any solvent that does not significantly inhibit this reaction can be used.
  • linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), dioxane; amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP); , these inert solvents can be used alone or in combination of two or more.
  • reaction temperature can be from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by recrystallization, purification by column chromatography, or the like. Alternatively, the next step may be performed without isolating the intermediate from the reaction system.
  • the benzimidazole compound represented by the general formula (1-2) is a benzimidazole compound represented by the general formula (1-3) and an acetylene compound represented by the general formula (4). known as the Sonogashira reaction using a palladium catalyst and a copper compound (Tetrahedron Lett. 1975, 50, 4467, Synthesis, 364-365 (1981), Organic Letters, 11(1), 221-224 2009).
  • Palladium catalysts that can be used include, for example, palladium(II) acetate, bistriphenylphosphinedichloropalladium(II), diphenylphosphinoferrocenedichloropalladium(II), tetrakis(triphenylphosphine)palladium(0), dichloro ditriphenylphosphinopalladium (0), tris(dibenzylideneacetone) dipalladium (0) and the like.
  • the amount of the palladium catalyst to be used is generally 0.01-0.5 mol per 1 mol of the compound represented by general formula (1-3).
  • Copper compounds that can be used include monovalent copper halides such as cuprous fluoride, cuprous chloride, cuprous bromide, and cuprous iodide; Divalent copper halides such as cupric and cupric iodide can be used.
  • the amount of the copper compound to be used is generally 0.1 to 1 mol per 1 mol of the compound represented by general formula (1-3).
  • a base is used in this reaction, and usable bases include sodium hydroxide, potassium hydroxide, calcium hydroxide, barium hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate, and cesium carbonate.
  • inorganic bases such as potassium phosphate, or amines such as triethylamine, pyridine and piperidine.
  • the amount of the base to be used is generally 1-10 mol per 1 mol of the compound represented by formula (1-3).
  • This reaction can be performed in a solvent.
  • the organic solvent that can be used is not particularly limited as long as it is inert to the reaction.
  • ether solvents such as dioxane, 1,2-dimethoxyethane and tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene, benzene and xylene
  • aliphatic hydrocarbon solvents such as n-pentane, n-hexane and n-heptane Solvent
  • amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide and N-methylpyrrolidone
  • nitrile solvents such as acetonitrile and benzonitrile
  • the reaction temperature is the temperature at which the coupling reaction can be completed, and is usually within the range from room temperature to the boiling point of the solvent used.
  • the reaction time is usually several minutes to several tens of hours.
  • the reaction is preferably carried out under an inert gas atmosphere.
  • the target product can be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary.
  • step [C] The benzimidazole compound represented by the general formula (1-1) is obtained by converting the benzimidazole compound represented by the general formula (1-2) to Greene's PROTECTIVE GROUPS in ORGANIC SYNTHESIS (4th Edition) 561-565
  • the protecting group can be deprotected according to the method described in et al.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by recrystallization, purification by column chromatography, or the like.
  • step [D] The benzimidazole compound represented by the general formula (1a) is obtained by combining the benzimidazole compound represented by the general formula (1-1) and the compound represented by the general formula (5) with a base and It can be produced by reacting in the presence of an inert solvent.
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, sodium acetate, acetic acid, Acetates such as potassium, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide; triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) tertiary amines such as pyridine, nitrogen-containing aromatic compounds such as dimethylaminopyridine (DMAP), and the like, and the amount used is usually for the compound represented by the general formula (1-1) It is used in the range of 1-fold molar to 10-fold molar.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium
  • the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
  • examples include aromatic hydrocarbons such as benzene, toluene and xylene; Hydrogens, diethyl ether, methyl tertiary butyl ether, dioxane, linear or cyclic ethers such as tetrahydrofuran (THF), amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), Ketones such as acetone and methyl ethyl ketone, polar solvents such as dimethylsulfoxide (DMSO) and 1,3-dimethyl-2-imidazolidinone (DMI), inert solvents such as alcohols such as methanol, ethanol, propanol and isopropyl alcohol can be exemplified, and these inert solvents can be used alone or in combination of two or more.
  • aromatic hydrocarbons such as
  • reaction temperature can be from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the compound of the present invention can be produced by purification by recrystallization, column chromatography, etc., if necessary.
  • the benzimidazole compound represented by the general formula (1′) is prepared by diluting the benzimidazole compound represented by the general formula (1a) in the presence of a catalytic reduction catalyst under normal pressure or under pressure. It can be produced by reacting under a hydrogen atmosphere in the presence or absence of an inert solvent.
  • catalytic reduction catalysts used in this reaction include palladium catalysts such as palladium-carbon and palladium hydroxide-carbon, and nickel catalysts such as Raney nickel.
  • the amount used is 0.001 to 0.1 molar equivalents with respect to the benzimidazole compound represented by the general formula (1a).
  • the reaction temperature may be appropriately selected within the range of ⁇ 20° C. to the reflux temperature of the solvent used, and the reaction time may be appropriately selected within the range of several minutes to 100 hours.
  • the reaction pressure may be appropriately selected within the range of 0.1 Mpa to 5 Mpa.
  • inert solvents include aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane; esters such as ethyl acetate, methyl acetate and butyl acetate; Amides such as formamide and dimethylacetamide, nitriles such as acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol and i-propanol, 1,3-dimethyl-2-imidazolidinone, acetic acid , organic acids such as propionic acid, or inert solvents such as water can be used, and these inert solvents can be used alone or in combination of two or more.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the compound of the present invention can be produced by purification by recrystallization, column chromatography, etc., if necessary.
  • a halopyrazole compound represented by general formula (3) can be produced by reacting a pyrazole compound represented by general formula (3-1) with a halogenating agent in the presence of an inert solvent.
  • the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
  • examples include halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile and propionitrile, Esters such as ethyl acetate, methyl acetate, and butyl acetate, amides such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone (NMP), 1,3-dimethyl-2-imidazolidinone (DMI ), alcohols such as methanol, ethanol, propanol, and isopropyl alcohol, and inert solvents such as organic acids such as acetic acid.
  • halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • nitriles such as acetonitrile and propionitrile
  • Esters such as ethyl acetate, methyl acetate
  • halogenating agent used in this reaction commercially available imidazoles such as NCS (N-chlorosuccinimide), NBS (N-bromosuccinimide), DBH (1,3-dibromo-5,5-dimethylhydantoin), DIH (1 , 3-diiodo-5,5-dimethylhydantoin) and the like.
  • reaction temperature can be from room temperature to the boiling point of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • the target product can be isolated from the reaction system containing the target product by a conventional method, and the compound can be produced by recrystallization, column chromatography, etc., if necessary.
  • the benzimidazole compound represented by the general formula (2) includes a benzimidazole compound represented by the general formula (2-1) and a compound PG-L (e.g., methoxymethyl chloride (MOMCl), methoxyethoxymethyl chloride (MEMCl ), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl)) in the presence of a base and an inert solvent.
  • PG-L e.g., methoxymethyl chloride (MOMCl), methoxyethoxymethyl chloride (MEMCl ), 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl)
  • Examples of the base used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, sodium acetate, acetic acid, Acetates such as potassium, alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, sodium ethoxide; triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) tertiary amines such as pyridine, nitrogen-containing aromatic compounds such as dimethylaminopyridine (DMAP), etc., and the amount thereof used is usually for the compound represented by the general formula (2-1) It is used in the range of 1-fold molar to 10-fold molar.
  • inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium
  • the inert solvent used in this reaction may be one that does not significantly hinder the progress of this reaction.
  • examples include aromatic hydrocarbons such as benzene, toluene, and xylene; Halogenated hydrocarbons; chlorobenzene, dichlorobenzene and other halogenated aromatic hydrocarbons, diethyl ether, methyl tertiary butyl ether, dioxane, tetrahydrofuran (THF) and other chain or cyclic ethers, ethyl acetate and other esters, dimethyl Formamide (DMF), dimethylacetamide (DMA), amides such as N-methylpyrrolidone (NMP), acetone, ketones such as methyl ethyl ketone, dimethyl sulfoxide (DMSO), 1,3-dimethyl-2-imidazolidinone (DMI ) can be exemplified, and these inert solvents can be used alone or in combination of two or more.
  • reaction temperature can be from room temperature to the boiling point range of the inert solvent used, and the reaction time varies depending on the reaction scale and reaction temperature, but may be carried out in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by recrystallization, purification by column chromatography, or the like. Alternatively, intermediates may be used without isolation from the reaction system.
  • Me is a methyl group
  • Et is an ethyl group
  • n-Pr is a normal propyl group
  • i-Bu is an isobutyl group
  • t-Bu is a tertiary butyl group.
  • Physical properties are indicated by melting point (° C.) or 1 H-NMR, and 1 H-NMR data are shown in Tables 5 and 6.
  • the agricultural and horticultural insecticidal acaricide and heartworm control agent of the present invention contain a benzimidazole compound represented by general formula (1) or (1-1) or a salt thereof as an active ingredient.
  • the agricultural and horticultural insecticide and acaricide containing the benzimidazole compound represented by the general formula (1) or general formula (1-1) or a salt thereof as an active ingredient of the present invention is used for paddy rice, fruit trees, vegetables, other crops and It is suitable for controlling various agricultural and forestry pests, horticultural pests, grain storage pests, sanitary pests, pests such as nematodes, and mites that damage flowers and plants.
  • Examples of the pests, nematodes, etc. are as follows. Lepidoptera pests such as Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapularis, Spodoptera exempta, and American white chick (Hyphantria cunea), Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, (Brachmia triannulella), Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera , Phalerodonta manleyi, Eumeta japonica, Pier
  • Hemiptera pests such as Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc.
  • Aeschynteles maculatus Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopterus Scale bug (Icerya purchasi), Japanese stink bug (Piezodorus hybneri), Rice stink bug (Lagynotomus elongatus), Rice leafhopper (Thaia subrufa), Rice black stink bug (Scotinophara lurida), Thorny aphid (Sitobion ibarae), Stink bug (Stariodes iwasakii) , Aspidiotus destructor, Taylorilygus pallidulus, Myzu
  • Coleoptera pests such as Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, Alfalfa weevil (Hypera postica), Echinocnemus squameus, Oulema oryzae, Oulema oryzae, Donacia provosti, Lissorhoptrus oryzophilus, Colasposoma dauricum, Euscepes postfascepes (Epilachna varivestis), Common bean weevil (Acanthoscelides obtectus), Western corn rootworm (Diabrotica virgifera virgifera), Involvulus cupreus, Aulacophora femoralis, Pea weevil (Bruchus pisorum), Epilachna vigintioctomaculata), Carpophilus dimidiatus,
  • Attagenus unicolor japonicus Pagria signata, Anomala rufocuprea, Palorus ratzeburgii, Alphitobius laevig atus), Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata, Xylotrechus pyrrhoderus, Epitrix cucumeris, Tomicus piniperda, Monochamus alternatus, Popillia japonica, Epicauta gorhami, Sitophilus zeamais, Rhynchites heroes, Listroderes costirostris , Callosobruchus maculatus, Phyllobius armatus, Anthonomus pomorum, Linaeidea aenea, and Anthonomus grandis.
  • Diptera pests such as Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and rice flies Fly (Hydrellia sasakii), Agromyza oryzae, Hydrellia griseola, Hydrellia griseola, Ophiomyia phaseoli, Cucurbit fly (Dacus cucurbitae), Drosophila suzukii, Anopheles spp.
  • Flea flies such as Rhacochlaena japonica, Muscina stabulans, Megaselia spiralis, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus , Anopheles sinensis, Hylemya brassicae, Asphondylia sp., Delia platura, Delia antiqua, Rhagoletis cerasi, Culex pipiens molestus Forskal, Ceratitis capitata, Bradysia agrestis, Pegomya cunicularia, Liriomyza sativae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Culex aegypti (Culex quinquef asciatus), Aedes aegypti, Aedes albopictus, Li
  • Hymenoptera pests such as Pristomyrmex ponnes, Antidae, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, Formica fusca japonica , wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., Fire ants (Solenopsis spp.), Arge mali, and blue ants (Ochetellusglaber) and the like.
  • Orthoptera Grasshopper pests
  • Homorocoryphus lineosus Gryllotalpa sp.
  • Oxya hyla intricata Oxya yezoensis
  • Locusta migratoria Oxya japonica
  • Oxya japonica Homorocoryphus jezoensis
  • Emma cricket Teogryllus emma
  • Thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, and Anascurthrips , Liothrips floridensis, Gladiolus simplex, Thrips nigropilosus, Heliothrips haemorrhoidalis, Pseudodendrothrips mori, Microcephalothrips abdominalis Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Scirtothrips dali ), Dendrothrips minowai, Haplothrips niger, Thrips tabaci, Thrips alliorum, Thrips hawaiiensis, Haplothrips
  • Examples of acarid pests include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Ticks such as Tetranychus viennensis, Tetranychus kanzawai, Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, Latrodectus Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes Sarcoptes, Sarcoptes scabiei, Haemaphysalis longicornis, Ixodes scapularis, Tyrophagus similis, Chey
  • termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes forsanus, Hodotermopsis japonica, Reticulitermes sp., Reticulitermes flaviceps amamianus , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odontotermes , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
  • Cockroach pests such as Periplaneta fuliginosa, Blattella germanica, Blatta orientalis, Periplaneta brunnea, Blattella lituricollis, Periplaneta japonica, and Periplaneta japonica (Periplaneta americana) and the like.
  • Flea order examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and chicken fleas (Ceratophyllus gallinae).
  • Nematodes such as Nothotylenchus acris, Aphelenchoides besseyi, Pratylenchus penetrans, Meloidogyne hapla, Meloidogyne incognita, Globodera rostochiensis), Java root nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Minaminegusare nematode (Pratylenchus coffeae), wheat negus nematode (Pratylenchus neglectus), and orange nematode (Tylenchus semipenetrans) and the like.
  • molluscs examples include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. are mentioned.
  • the agricultural and horticultural insecticide of the present invention also has a strong insecticidal effect against another pest, Tuta absoluta.
  • animal parasitic ticks that are one of the objects to be controlled include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, and Haemaphysalis campanulata.
  • fleas to be controlled include, for example, ectoparasitic wingless insects belonging to the order Siphonaptera, more specifically fleas belonging to the family Pulicidae and Ceratephyllus.
  • fleas belonging to the family Ctenocephalides include, for example, dog flea (Ctenocephalides canis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken lift flea (Echidnophaga gallinacea), cheops rat flea (Xenopsylla cheopis), mole flea ( Leptopsylla segnis), European rat flea (Nosopsyllus fasciatus), and black rat flea (Monopsyllus anisus).
  • Still other ectoparasites to be controlled include, for example, bovine lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), bovine nits (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), and lice such as dog lice (Trichodectes canis), bullflies (Tabanus trigonus), culicoides schultzei (Culicoides schultzei), and blood sucking diptera (Simulium ornatum) pests, etc.
  • endoparasites such as lungworms, nematodes, nodular worms, gastric parasites, roundworms, and nematodes such as heartworms; Tapeworms, such as tapeworms, tapeworms, tapeworms, tapeworms, and tapeworms, flukes, such as Schistosoma japonicum, and liver flukes, as well as coccidia, malaria parasites, intestinal sarcosporidia, toxoplasma , and protozoa such as Cryptosporidium.
  • Enoplida parasites Trichuris subgenus (Trichuris spp.), Capillaria subgenus (Capillaria spp.), Trichomosoides subgenus (Trichomosoides) spp.), subgenus Trichinella (genus Trichinella), order Rhabditia, e.g., subgenus Micronema spp., subgenus Strongyloides spp., roundworms Orders Strongylida such as Stronylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp.
  • Gyalocephalus spp. Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp. .), subgenus Esophagostomum (genus Oesophagostomum spp.), subgenus Chabertia (Chabertia spp.), subgenus Stephanurus (pig kidneyworm) (Stephanurus spp.), subgenus Ancilostoma (Zwini Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Chiastoma Subgenus Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp.
  • Neostrongylus spp. Cystocaulu s spp.
  • Pneumostongylus spp. Spicocaulus spp.
  • Elaphostrongylus spp. Parelaphostrongylus spp.
  • Klenosoma Crenosoma spp.
  • subgenus Paracrenosoma spp. subgenus Angiostrongylus (Angiostrongylus spp.), subgenus Aelurosutrongylus spp.
  • subgenus Filaroides spp. Parafilaroides spp.
  • Trichostrongylus spp. Haemonchus spp.
  • subgenus Marshallagia spp. subgenus Cooperia spp.
  • subgenus Nematodirus Nematodirus spp.
  • subgenus Hyostrongylus spp. subgenus Obeliscoides spp.
  • subgenus Amidostomum Amidostomum spp.
  • subgenus Orlanus Ollulanus spp.
  • Oxyurida parasites Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp. , Aspiculuris subgenus (Aspiculuris spp.), Heterakis subgenus (Heterakis spp.), etc.;
  • Ascaridia parasites Ascaris spp., Toxocaris spp., Toxocara spp., Parascaris spp. ) (Parascaris spp.), subgenus Anisakis (Anisakis spp.), subgenus Ascaridia (roundworm) (Ascaridia spp.), order Spirridae (Thirdata) (Spirurida), e.g. ) (Gnathostoma spp.), Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp. ), Draschia spp. , Dracunculus subgenus (Medina worm) (Dracunculus spp.), etc.;
  • Filariida Subgenus Stephanofilaria spp., Subgenus Parafilaria spp., Subgenus Setaria spp., Subgenus Loa spp., Subgenus Girofilariae (Canine Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., etc.;
  • canine filariasis refers to nematodes of the order Spirurida, in particular, (a) nematodes of the family Onchocercidae, for example, Brugia spp. Brugia malayi, Brugia pahangi, Brugia patei; Dipetalonema spp., Dipetalonema reconditum; Dirofilaria spp., Dirofilaria immitis; Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis , Onchocerca gibsoni, Onchocerca gutturosa; (b) Nematodes of the Setariidae family, such as Setaria spp., Setaria digitata, Setaria equina, Setaria labiatopapillosa, Setaria marshalli; Wuchereria spp., Wuchereria bancrofti; (c) Heartworms Nematodes of the family Filariidae,
  • Parafilaria spp. ; Stephanofilaria assamensis of the spp. Stephanofilaria spp. , Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi ), etc., but is not limited to these.
  • the target animals of the canine heartworm control agent of the present invention are domestic animals such as cows, pigs, rabbits and birds, or pets such as dogs, rabbits and cats (hereinafter target animals, excluding humans). , preferably dogs, but not limited to these.
  • target animals excluding humans
  • control includes prevention and treatment.
  • the endoparasite control agent containing a benzimidazole compound or a salt thereof represented by the general formula (1) or general formula (1-1) of the present invention as an active ingredient is a parasite that lives in the body of an intermediate host and a final host Not only that, it also exerts an effect on parasites in the living body of the host.
  • the benzimidazole compound represented by the general formula (1) or general formula (1-1) of the present invention or a salt thereof exerts its effect on all developmental stages of parasites. For example, in protozoa, there are cysts, pre-cysts, vegetative or asexual mitotic bodies, amoeba bodies, sexual gametocytes, gametes, fusion bodies, sporophytes and the like.
  • nematodes In nematodes, they are eggs, larvae and adults. Furthermore, the compound according to the present invention not only exterminates parasites in vivo, but can also prevent parasite infection prophylactically by applying it to an environment that is an infection route.
  • an infection route For example, soil-borne infection from the soil of fields and parks, percutaneous infection from water systems such as rivers, lakes, wetlands, and paddy fields, oral infection from feces of animals such as dogs and cats, saltwater fish, freshwater fish, and crustaceans. It is possible to prevent oral infections from shellfish, livestock raw meat, etc., and infections from mosquitoes, horseflies, flies, cockroaches, ticks, fleas, lice, kissing bugs, tsutsugamushi, etc.
  • an effective amount of the compounds of the present invention can be administered orally, injected (intramuscularly, subcutaneously, intravenously, intraperitoneally) together with pharmaceutical additives. ); transdermal administration such as dipping, spraying, bathing, washing, pouring-on and spotting-on and dusting; nasal administration.
  • the compounds of the present invention can also be administered in shaped articles using strips, plates, bands, collars, ear marks, limb bands, labeling devices and the like.
  • the compound of the present invention can be made into any dosage form suitable for the route of administration.
  • Solid preparations such as powders, granules, wettable powders, pellets, tablets, boluses, capsules, shaped articles containing the active compound; injectable solutions, oral solutions, on the skin or in body cavities, for any dosage form.
  • liquid preparations used in the preparation liquid preparations used in the preparation; solution preparations such as pour-on preparations, spot-on preparations, flowable preparations and emulsions; semi-solid preparations such as ointments and gels.
  • Solid preparations can be used mainly for oral administration or for transdermal administration after being diluted with water or the like, or for environmental treatment.
  • Solid preparations can be prepared by mixing the active compound with suitable excipients, if necessary adding auxiliaries, and shaping into the desired shape. Suitable excipients include, for example, inorganic substances such as carbonates, bicarbonates, phosphates, aluminum oxide, silica, clays, organic substances such as sugars, cellulose, ground grains, starch.
  • Injectable solutions can be administered intravenously, intramuscularly and subcutaneously.
  • Injectable solutions are prepared by dissolving the active compound in a suitable solvent and, if necessary, adding solubilizers, acids, bases, buffer salts, antioxidants. and additives such as protective agents.
  • Suitable solvents include water, ethanol, butanol, benzyl alcohol, glycerin, propylene glycol, polyethylene glycol, N-methylpyrrolidone and mixtures thereof, physiologically acceptable vegetable oils, synthetic oils suitable for injection, and the like.
  • Solubilizers include polyvinylpyrrolidone, polyoxyethylated castor oil and polyoxyethylated sorbitan esters.
  • Protecting agents include benzyl alcohol, trichlorobutanol, p-hydroxybenzoates and n-butanol.
  • Oral liquids can be administered directly or diluted. It can be prepared in the same manner as the injectable solution.
  • Flowables, emulsions, etc. can be administered directly or diluted transdermally, or by environmental treatment.
  • Liquid agents for use on the skin can be administered by dripping, spreading, rubbing, spraying, spreading, or applying by immersion (immersion, bathing or washing). These solutions can be prepared similarly to injectable solutions.
  • Drops and laxatives can be prepared by dissolving, suspending or emulsifying the active ingredient in suitable skin-compatible solvents or solvent mixtures. If necessary, auxiliaries such as surfactants, colorants, absorption promoters, antioxidants, light stabilizers and adhesives may be added, and solvents include water, alkanols, glycols, polyethylene glycols, polypropylene glycols.
  • glycerin benzyl alcohol, phenylethanol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, liquid paraffin, light liquid paraffin, silicone, dimethylacetamide, N-methylpyrrolidone or 2,2-dimethyl-4-oxymethylene-1,3-dioxolane.
  • Absorption enhancers include DMSO, isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty esters, triglycerides and fatty alcohols.
  • Antioxidants include sulfites, metabisulfites, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole and tocopherols.
  • Emulsions can be administered orally, transdermally or as an injection.
  • Emulsions are prepared by dissolving an active ingredient in a hydrophobic phase or a hydrophilic phase, mixing this with a suitable emulsifier and, if necessary, further adding a colorant, an absorption-promoting substance, a protective agent, an antioxidant, a light-shielding agent, a thickening substance, and the like. can be prepared by homogenization with the solvent of the other phase together with the adjuvant of
  • Hydrophobic phases include paraffin oil, silicone oil, sesame oil, almond oil, castor oil, synthetic triglycerides, ethyl stearate, di-n-butyryl adipate, hexyl deurate, dipropylene glycol pelargonate, branched Esters of linear short-chain fatty acids with saturated fatty acids of C 16 -C 18 chain length, isopropyl myristate, isopropyl palmitate, caprylic/capric esters of saturated fatty alcohols of C 12 -C 18 chain length, stearic acid isopropyl, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid ester, dibutyl phthalate, diisopropyl adipate, isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, o
  • the hydrophilic phase includes water, propylene glycol, glycerin, and sorbitol.
  • Emulsifiers include nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glyceryl monostearate, polyoxyethyl stearate, alkylphenol polyglycol ethers. Active agents; amphoteric surfactants such as disodium N-lauryl ⁇ -iminodipropionate, lecithin; anionic such as sodium lauryl sulfate, fatty alcohol sulfate ethers, monoethanolamine salts of mono/dialkyl polyglycol orthophosphates Surfactants; cationic surfactants such as cetyltrimethylammonium chloride and the like.
  • nonionic surfactants such as polyoxyethylated castor oil, polyoxyethylated sorbitan monoolefinate, sorbitan monostearate, glyceryl monostearate, polyoxyethy
  • adjuvants include carboxymethylcellulose, methylcellulose, polyacrylate, alginate, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, methyl vinyl ether, maleic anhydride copolymer, polyethylene glycol, wax, and colloidal silica.
  • Semi-solid preparations can be administered by coating or spreading on the skin or by introduction into body cavities. Gels can be prepared by adding to the solution prepared as described above for the injectable solution sufficient thickener to produce a clear material having an ointment-like consistency.
  • the agent for controlling endoparasites of the present invention is used as a medicine for mammals other than humans or animals belonging to birds
  • the optimum amount (effective amount) of the active ingredient depends on treatment or prevention, the type of infected parasites, and the type of infection.
  • oral administration ranges from about 0.0001 to 10,000 mg/kg body weight per day, although it varies depending on the degree, dosage form, and the like.
  • parenteral administration about . 0001 to 10000 mg/kg body weight, given in single or divided doses.
  • the concentration of the active ingredient in the internal parasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably 0.001 to 99%, more preferably about 0.005 to 20% by mass.
  • the endoparasite control agent of the present invention may be a composition to be administered as it is, or a high-concentration composition diluted to an appropriate concentration at the time of use.
  • existing internal parasite control agents can be used in combination for the purpose of reinforcing or complementing the effects of the internal parasite control agent of the present invention.
  • a formulation in which two or more active ingredients are mixed before administration may be used, or two or more different formulations may be administered separately.
  • the agricultural and horticultural insecticide and acaricide containing the benzimidazole compound represented by general formula (1) or general formula (1-1) or a salt thereof of the present invention as an active ingredient can be used for paddy field crops, upland crops, fruit trees, vegetables, Since it has a remarkable control effect against the above-mentioned pests that damage other crops and flowers, etc., the seedling raising facility,
  • the intended effects of the agricultural and horticultural insecticide and acaricide of the present invention can be obtained by treating cultivation carriers such as paddy fields, fields, fruit trees, vegetables, other crops, seeds such as flowers, paddy water, foliage or soil. It is something that can be done.
  • the compound of the present invention is absorbed from the roots, with or without the soil, by treating it with seedling soil for crops, flowers, etc., planting hole soil at the time of transplanting, stock base, irrigation water, cultivation water in hydroponics, etc.
  • a preferred form of use is application utilizing the so-called systemic migration property by allowing
  • Useful plants for which the agricultural and horticultural insecticide and acaricide of the present invention can be used are not particularly limited. Soybeans, adzuki beans, broad beans, peas, kidney beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables ( Cabbage, tomato, spinach, broccoli, lettuce, onion, green onion, bell pepper, eggplant, strawberry, pepper, okra, chive, etc.), root vegetables (carrot, potato, sweet potato, taro, radish, turnip, lotus root) , burdock, garlic, shallots, etc.), processed crops (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), gourds (pumpkin, cucumber, watermelon, makuwa melon, melons, etc.
  • plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, and sethoxydim. Also included are plants that have been given tolerance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
  • HPPD inhibitors such as isoxaflutole
  • ALS inhibitors such as imazethapyr and thifensulfuron-methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate
  • sethoxydim plants that have been given tolerance to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba
  • plants that have been made tolerant by classical breeding methods are rape, wheat, sunflower and rice that are tolerant to imidazolinone ALS-inhibiting herbicides such as imazethapyr, under the trade name of Clearfield®. is already on sale.
  • soybeans that are tolerant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl by classical breeding methods and are already on the market under the trade name of STS soybeans.
  • SR corn and the like are examples of plants that have been made tolerant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides by classical breeding methods.
  • plants endowed with resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990).
  • Mutant acetyl-CoA carboxylase resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. 53, pp. 728-746 (2005).
  • a plant resistant to an acetyl-CoA carboxylase inhibitor can be produced by introducing a plant acetyl-CoA carboxylase-related mutation into a plant acetyl-CoA carboxylase. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318. By introducing substitution mutations, plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc. can be produced, and the agricultural and horticultural insecticide and acaricide of the present invention can be applied to these plants as well. can be done.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popiliae; insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, rufin, saporin, bryozin; Steroid metabolizing enzymes such as hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitors; HMG-CoA reduc
  • Toxins expressed in such transgenic plants include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, VIP1, VIP2, VIP3 or VIP3A. Also included are insecticidal protein hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are created using recombinant techniques by new combinations of different domains of these proteins. As a partially deleted toxin, Cry1Ab with partially deleted amino acid sequence is known. A modified toxin has one or more of the amino acids of the native toxin substituted.
  • the toxins contained in these recombinant plants especially confer resistance to Coleoptera pests, Hemiptera pests, Diptera pests, Lepidoptera pests, and nematodes.
  • the agricultural and horticultural insecticide and acaricide of the present invention can be used in combination with those techniques or systematized.
  • the agricultural and horticultural insecticidal and acaricidal agent of the present invention is used as it is for controlling various pests, or in the form of being appropriately diluted with water or the like, or in the form of being suspended. It may be used for plants where the occurrence of is predicted, for example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, immersion of seeds in chemicals, seed dressing, Seed treatment such as Culper treatment, soil all layer mixing, row application, bed soil mixing, cell seedling treatment, planting hole treatment, stock base treatment, top dressing, rice box treatment, water surface application, etc. It can also be used by being absorbed from the roots.
  • Seed treatment such as Culper treatment, soil all layer mixing, row application, bed soil mixing, cell seedling treatment, planting hole treatment, stock base treatment, top dressing, rice box treatment, water surface application, etc. It can also be used by being absorbed from the roots.
  • the agricultural and horticultural insecticidal and acaricidal agent of the present invention can be used as it is, or in the form of being diluted or suspended with water, etc., in an effective amount for controlling pests in a place where the occurrence of the pests is expected.
  • it in addition to spraying against grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on building materials, smoke, bait, and the like.
  • Seed treatment methods include, for example, a method of immersing seeds in a liquid or undiluted liquid state to allow the drug to permeate, a method of mixing solid or liquid preparations with seeds, and a method of dressing. Examples include a method of treating and adhering to the surface of seeds, a method of coating seeds by mixing with an adhesive carrier such as resin or polymer, and a method of spraying near seeds at the same time as planting.
  • the "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation. Mention may be made of plants for vegetative propagation.
  • the "soil” or “cultivation carrier” for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that allows plants to grow may be used, such as so-called soil, seedling mats, water, etc. Specific materials include sand, pumice, vermiculite, diatomaceous earth, agar, gelatinous substances, high It may be a molecular substance, rock wool, glass wool, wood chips, bark, or the like.
  • liquid formulations such as emulsion concentrates and flowable formulations, or solid formulations such as wettable powders or wettable granules
  • a method of spraying a method of spraying dust, or smoking.
  • a method of applying to the soil for example, a method of applying a liquid formulation to the stock of a plant or a nursery for raising seedlings without diluting it with water, A method of spraying on nurseries, etc., a method of spraying powders, wettable powders, wettable granules, granules, etc.
  • a method of planting holes before sowing or planting plants examples thereof include a method of spraying powders, wettable powders, wettable granules, granules, etc. on the strips.
  • the dosage form may vary depending on the application period, such as application at the time of sowing, application at the time of greening, and application at the time of transplanting. It should be applied in a mold. It can also be applied by mixing with potting soil, and mixing potting soil with powders, wettable granules, granules, etc., for example, mixing with bed soil, mixing with covering soil, mixing with the whole potting soil, etc. Can be done. Simply alternating layers of potting soil and various formulations may be applied.
  • solid formulations such as jumbo formulations, pack formulations, granules and wettable granules, and liquid formulations such as flowables and emulsions are usually sprayed over flooded paddy fields.
  • a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer.
  • chemical solutions such as emulsions and flowables at water outlets, irrigation systems, and other sources of water flowing into paddy fields, it is possible to apply the chemicals in a labor-saving manner along with the supply of water.
  • the treatment can be applied to seeds or cultivation carriers close to plants during the period from seeding to seedling raising.
  • the agent for plants that are directly sown in a field, it is preferable to apply the agent directly to the seeds as well as to the base of the plant under cultivation.
  • Spray treatment using granules, or irrigation treatment in the form of a liquid diluted or undiluted drug can be performed. It is also a preferred treatment to mix the granules with the cultivation carrier before sowing and then sowing.
  • the irrigation treatment of liquid chemicals or the spraying treatment of granules to the nursery bed for raising seedlings is preferable.
  • the agricultural and horticultural insecticide and acaricide of the present invention is generally formulated into a form convenient for use according to a conventional method for agricultural chemical formulations.
  • the benzimidazole compound represented by the general formula (1) or the general formula (1-1) of the present invention or a salt thereof is added to a suitable inert carrier, or if necessary together with an adjuvant, a suitable Appropriate formulations such as suspensions, emulsions, liquids, wettable powders, wettable granules, granules, powders, tablets , packs, etc., for use.
  • the composition of the present invention may contain additive components commonly used in agricultural chemical formulations or animal parasite control agents, in addition to active ingredients, if necessary. can.
  • the additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreaders, spreading agents, antifreeze agents, , anti-caking agents, disintegrants, anti-degradants and the like.
  • antiseptics, plant pieces, etc. may be used as additive components. These additive components may be used alone or in combination of two or more.
  • solid carriers examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as plant powders (e.g.
  • plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea
  • examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), and the like. These may be used alone or in combination of two or more.
  • liquid carriers examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol and glycerin.
  • polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ethers normal paraffin, naphthene, isoparaffin, kerosene, mineral oil and other aliphatic hydrocarbons, benzene, toluene, xylene, solvent naphtha, alkylnaphthalene and other aromatic hydrocarbons, dichloromethane, chloroform, carbon tetrachloride, etc.
  • Halogenated hydrocarbons esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, and dimethyl adipate, lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, and N-alkylpyrrolidinone nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • Surfactants used as dispersants and wetting agents include, for example, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol,
  • binders and tackifiers include carboxymethyl cellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weights of 6,000 to 20,000.
  • cephalin, lecithin, etc. cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, crosslinked polyvinylpyrrolidone, copolymer of maleic acid and styrenes coalescence, (meth)acrylic acid-based copolymer, half ester of polyhydric alcohol polymer and dicarboxylic acid anhydride, water-soluble salt of polystyrene sulfonic acid, paraffin, terpene, polyamide resin, polyacrylate, polyoxy Ethylene, wax, polyvinyl alkyl ether, alkylphenol-formalin condensate, synthetic resin emulsion and the like.
  • Thickeners include, for example, xanthan gum, guar gum, daiyutan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch compounds, water-soluble polymers such as polysaccharides, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica, white carbon) and the like are included.
  • coloring agents include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
  • Antifreeze agents include, for example, polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Auxiliaries for caking prevention and disintegration promotion include, for example, starch, polysaccharides such as alginic acid, mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, copolymer of methacrylic acid ester, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • antidegradants examples include drying agents such as zeolite, quicklime and magnesium oxide, antioxidants such as phenol compounds, amine compounds, sulfur compounds and phosphoric compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. be done.
  • antiseptics examples include potassium sorbate and 1,2-benzothiazolin-3-one.
  • other aids such as functional spreaders, activity enhancers such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers. agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and it may be appropriately selected from the range of 0.01 to 90 parts by weight per 100 parts by weight of the agricultural and horticultural insecticide and acaricide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight of the total weight of the agricultural and horticultural insecticide and acaricide
  • 0.01 to 50 parts by weight 0.01 to 50% by weight of the total weight of the agricultural and horticultural insecticide and acaricide
  • the amount of the agricultural and horticultural insecticide and acaricide of the present invention to be used depends on various factors such as the purpose, target pests, crop growth conditions, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application place, and application time. Although it varies depending on factors such as the above, it may be appropriately selected according to the purpose from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares of the active ingredient compound.
  • the agricultural and horticultural insecticide and acaricide of the present invention can be used for the purpose of expanding the control target pests and the appropriate control period, or for the purpose of reducing the dosage. , fungicides, biopesticides, and the like, and can also be used in combination with herbicides, plant growth regulators, fertilizers, and the like, depending on the situation.
  • XMC 3,5-xylylmethylcarbamate
  • BPMC fenobucarb
  • Bt toxin insecticidal compound CPCBS(chlorfenson), DCIP(dichlorodiisopropyl ether), D-D(1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethylphosphorothioate (DSP), O- ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid ), acetoprole, acephate, abamectin
  • cadusafos cadusafos, kappa-tefluthrin, kappa-bifenthrin, cartap, carbaryl, carbosulfan, carbofuran, gammacyhalothrin (gamma-cyhalothrin), xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorane traniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorphenapyr, chlorfenson, Chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salition, cyhalodiamide ( cyhalodiamide), cyanophos (CYAP),
  • Agricultural and horticultural fungicides used for similar purposes include, for example, aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, acibenzolar-S- methyl), azoxystrobin, anilazine, amisulbrom, aminopyrifen, ampropylfos, ametoctradin, allyl alcohol, aldimorph ), amobam, isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole ), ipflufenoquin, iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate , iminoctadine-triacetate, imibenconazole, inpyrfluxam, unicon
  • streptomycin spiroxamine sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor, thiabendazole, thioximide tioxymid, thioquinox, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox, thiram, decaf decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole, tebufloquin, dodicin dodicin, dodine, bisethylenediamine copper complex (II) dodecylbenzenesulfonate (DBEDC), dodemorph, drazoxolone, triadimenol, triadimefon,
  • herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, acronifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor ), atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole , aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametryn, alachlor, allidochlor, all
  • saflufenacil cyanazine, cyanatryn, di-allate, diuron, diethamquat, dicamba, cycluron, cycloate, cyclooxydim ), diclosulam, cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop diclofop, diclofop-methyl, dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine (dinitramine), cinidon-ethyl, dinosam, cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl , diphenamid, difenoxuron, difenopenten, difenzoquat, cybutryne, c
  • terbacil daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, Thiocarbazil, tioclorim, thiobencarb, thiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmethrin (desmetryn), tetflupyrolimet, tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione , tembotrione, delachlor, terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam ), triasulfuron,
  • fenasulam phenisopham, fenuron, fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol, fenoprop, phenobenzuron, fenquinotrione, fenthiaprop, fenteracol, fentrazamide, phenmedipham , phenmedipham-ethyl, butachlor, butafenacil, butamifos, buthiuron, butidazole, butylate, buturon, butenachlor , butroxydim, butralin, butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl ), fluazifop, fluazifop-P, fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, flu
  • biopesticides for example, Agrobacterium radiobacter (e.g., "Galltrol-A®” from “AgBioChem, CA” using strain K84, “Becker Underwood” using strain K1026). "Nogall (registered trademark)” manufactured by , US”), Agrobacterium radiobacter (for example, “Bacterose (registered trademark)” manufactured by "Nippon Nohyaku Co., Ltd.” using strain 84), Ampelomyces quisqualis (e.g. "AQ 10®” from “IntrachemBio Italia & Co. KG” using strain AQ10), Aspergillus flavus (e.g.
  • Bacillus amyloliquefaciens for example, “Impression Clear (registered trademark)” manufactured by “Idemitsu Agri Co., Ltd.” using strain AT-332, and “University of Pretoria” using strain B246) "Avogreen®” from “Etec Crop Solutions, NZ”, strain D747 (e.g. “Bacstar®” from “Etec Crop Solutions, NZ”, “Shelter ( “Artemis®” from “Dagutat Biolab, ZA” using strain DB102, “RhizoVital®” from “ABiTEP, DE” using strain FZB42, strain GB03.
  • BioNeem® from “AgoGreen” using strain I-1582
  • Bacillus ⁇ Bacillus lacticola for example, “Micro Flo Company”
  • Bacillus lactimorbus for example, “Micro Flo Company”
  • Bacillus lactis for example, “Micro Flo Company”
  • Bacillus laterosporus e.g., "Bio-Tode®” manufactured by "Agro-Organics, SA”
  • Bacillus licheniformis Bacillus licheniformis (Bacillus licheniformis (e.g. "EcoGuard Biofungicide®” from “Novozymes” using strain SB3086)
  • Bacillus maroccanus e.g.
  • Colmeri for example, "TianBaoBTc®” from “Changzhou Jianghai Chemical Factory"
  • Bacillus thuringiensis tenebrionis Bacillus thuringiensis tenebrionis (Bacillus thuringienses tenebrionis) (e.g. "Novodor FC®” from “BioFa DE” using strain NB 176)
  • Bacillus thuringiensis var. san diego e.g. "Bacillus thuringiensis "M-One (registered trademark)” manufactured by var. san diego)
  • Beauveria bassiana e.g. "Naturalis®” from “Intrachem Bio Italia” and “Bove Max®” from “Novozymes” using strain CG716, strain F-263 "Biorisa Madara (registered trademark)” manufactured by “Idemitsu Kosan Co., Ltd.”, "Botaniguard wettable powder (registered trademark)” manufactured by “ARYSTA” using strain GHA, “Terragena,” using strain HF23, Inc.'s 'balEnce', 'BioWorks Inc.'s 'BotaniGard ES' using strain GHA, 'BioCeres WP' made by 'BioSafe Systems' using strain ANT-03), Beauveria brongniarti.
  • Beauveria brongniartii e.g. "Beaupro®” from “Andermatt Biocontrol AG”
  • Bradyrhizobium japonicum e.g. “Optimize®” from “Novozymes”
  • Burkholderia spp. e.g. "MBI-206 TGAI®” from “Marrone Bio Innovations” using strain A396)
  • Candida oleophila e.g., "Aspire®” from “Ecogen Inc., US” using strain I-82 and “Nexy®” from “BioNext” using O strain).
  • Candida saitoana e.g. “BIOCURE®” from “Micro Flo Company, US (BASF SE)”
  • Chaetomium cupreum e.g. “AgriLife” "BIOKUPRUM®” from “Rivale”
  • Chaetomium globosum e.g. "Rivadiom®” from “Rivale”
  • Chromobacterium subtsugae e.g.
  • strain PRAA4 "Grandevo®” from “Marrone Bio Innovations” using -1T Cladosporium cladosporioides (e.g. from “Cladosporium cladosporioides”), Chronostakis rosea catenulata (from “Cladosporium cladosporioides”) Clonostachys rosea f. catenulate) (e.g. "PRESTOP®” from "Verdera, Finland” using strain J1446), Colletotrichum gloeosporioides (e.g.
  • Coniothyrium minitans e.g., "Contans®” from “Encore Technologies, LLC” using strain CON/M/91-08
  • Cryptococcus Cryptococcus albidus e.g. "YieldPlus®” from “Anchor Bio Technologies, ZA”
  • Delftia acidovorans e.g. "Brett Young Seeds' BioBoost®
  • Dilophosphora alopecuri e.g. Twist Fungus®
  • Drechsrela monoceras e.g. strain MTB-951).
  • Fusarium oxysporum e.g., "Marcalite” manufactured by “Eisai Seikaken” using strain 101-2
  • Fusarium oxysporum e.g., “Natural Plant Protection” using strain Fo47 “Fusaclean (registered trademark)” from “AgBio Inc.”
  • Gliocladium spp. for example, “Prestop (registered trademark)” from “AgBio Inc.” using strain J1446, and Stoneman Company LLC
  • Hirsutella thompsonii e.g. "Mycohit®” from "Agro Biotech Research Center, IN
  • Lactobacillus acidophilus e.g.
  • Monacrosporium phymatopagum for example, “Nemahithon (registered trademark)” manufactured by “Tomoe Chemical Industry Co., Ltd.”
  • Mucor haemelis for example, manufactured by “Indore Biotech Inputs & Research” “BioAvard®”
  • Muscodor albus e.g. "Arabesque” from “Bayer Crop Science” using strain QST 20799
  • Myrothecium verrucaria e.g.
  • Pasteuria ni shizawae e.g. "oyacystLF/ST®” from “Pasteuria Bioscience” or “Clariva pn” from “Syngenta” using strain Pn1
  • Pasteuria penetrans e.g. "Pasteuria "Pasteuria” from “Pasteuria Bioscience”
  • Pasteuria usagae e.g. "Econem” from “Pasteuria Bioscience”
  • Pantoea agglomerans e.g.
  • strain E325) "Bloomtime Biological FD Biopesticide” manufactured by “Nufarm US”
  • Pectobacterium carotovorum for example, “Biokeeper (registered trademark)” manufactured by “Nissan Chemical Co., Ltd.” and CGE234M403 strain “Ecomate®” from “Kumiai Chemical” using strain 94-44B
  • Phoma macrostroma e.g. "Phoma H®” from “Scotts, US” using strain 94-44B.
  • Penicillium bilaii e.g. "Jump Start®” from “Novozymes”
  • Phlebiopsis gigantea e.g.
  • strain FOC PG B22/SP1190/3.2 " "ROTSOP®” from “Verdera, Finland”
  • Pochonia chlamydosporia var. catenulata e.g. "The National Center of Animal and Plant Health (CENSA); registered trademark)
  • Pseudomonas aureofaciens e.g. "Spot-Less Biofungicide®” from “Eco Soils Systems, CA” using strain TX-1
  • Pseudomonas chlororaphis e.g.
  • Pseudomonas fluorescens for example, "Frostban D®” from “Frost Technology Corp” using strain 1629RS or “Blightban®” from “Blightban” using strain A506, strain FPT- "Konae Fukuto (registered trademark)” manufactured by "Taki Chemical Co., Ltd.” using 9601, "Cell Seed Genki (registered trademark)", “Veggie Keeper (registered trademark)” manufactured by "Arista Life Sciences Co., Ltd.” using strain G7090), Pseudomonas proradix (for example, [Proradix (registered trademark)]), Pseudomonas resinovorans (e.g.
  • Bioprepraty, CZ using strain DV74 or M1) Polyversum®”
  • Reynoutria sachlinensis e.g. “REGALIA®” from “Marrone BioInnovations, US”
  • Rhizopogon amylopogon e.g. “Helena Chemical Company”
  • Myco-Sol® from “Helena Chemical Company”
  • Rhizopogon fulvigleba e.g. "Myco-Sol®” from “Helena Chemical Company”
  • Saccharomyces cerevisiae e.g. from “Lesaffre et Compagnie, FR”
  • Sclerotinia minor e.g. "Sarritor” from “Agrium Advanced Technologies”
  • Serratia entomophila Serratia entomophila
  • Sporothrix insectorum e.g.
  • strain K61 "Mycostop®” from “Verdera”, Streptomyces lydicus (e.g. strain WYEC108).
  • ACTINOVATE® from “Natural Industries, US”
  • Streptomyces saraceticus e.g., "Clanda®” from “A & A Group (Agro Chemical Corp.)”).
  • Talaromyces flavus for example, "Momi Keeper (registered trademark)” manufactured by “Central Glass Co., Ltd.” using strain B-422, and “Idemitsu Kosan using strain SAY-Y-94-01 “Tough Block (registered trademark)” manufactured by Co., Ltd., "PROTUS (registered trademark) WG” manufactured by "Prophyta, DE” using strain V117b), Trichoderma asperellum (for example, strain ICC 012) "Isagro” used, "T34 Biocontrol (registered trademark)” manufactured by “Bioncontrol Technologies, ES” using strain T34, “ECO-HOPE” manufactured by "Kumiai Chemical Industry Co., Ltd.” using strain SKT-1 (registered trademark)”), Trichoderma atroviride (for example, “Esquive (registered trademark) WP” manufactured by "Agrauxine, FR” and “Tenet” manufactured by “Agrimm Technologies Ltd, NZ” using strain LC52 (
  • T-Gro 7456 from “Dagutat Biolab” using strain DB 103) ", “Trianum-P®” from “Koppert” using strain ITEM908, “Trichoplus®” from “Biological Control Products, SA” using strain KD, using strain TH-35 "ROOT PRO (registered trademark)” made by “Mycontrol Ltd.”), Trichoderma harzianum rifai (for example, “PLANTSHIELD T -22G (registered trademark)” and “TR ICHODEX®”), Trichoderma lignorum (e.g.
  • Trichoderma polysporum for example, “Binab TF WP (registered trademark)” manufactured by “BINAB Bio-Innovation AB, Sweden"), Trichoderma stromaticum (for example, “TRICOVAB (registered trademark)” manufactured by “Ceplac; Brazil”), Trichoderma virens (e.g. “SOILGARD®” from “Certis LLC, US” using strain GL-21), Trichoderma viride (e.g. using strain ICC080) "REMEDIER (registered trademark) WP” manufactured by Isagro Ricerca, ITALIA, and “Trianum-P (registered trademark)” manufactured by "Koppert” using strain TV1),
  • Tsukamurella paurometabola e.g. 'HeberNem®' using strain C-924
  • Ulocladium oudemansii e.g. 'Botry-Zen Ltd, NZ' using strain HRU3
  • Botry-Zen (registered trademark) manufactured by "BioWorks Inc.” using strain U3
  • Variovorax paradoxus for example, using strain CGF4526 "Central Glass "Field Keeper Wettable Powder (registered trademark)”
  • VA ((Vesicular-Arbuscular Mycorrhiza) mycorrhizal fungi (for example, "Dr Kincon (registered trademark)” manufactured by "Idemitsu Agri")
  • Verticillium Verticillium alboatrum e.g.
  • Example 2 Preparation of 1-ethanesulfonyl-2-(3-tert-butyl-4-trimethylsilylethynyl-1H-pyrazol-1-yl)benzimidazole (Compound No. 2-5) 2-(3-tert-butyl-4-trimethylsilylethynyl-1H-pyrazol-1-yl)benzimidazole (0.23 g, 0.68 mmol) was dissolved in THF (8.6 mL) and triethylamine (0.67 mL). , 60% sodium hydride (80 mg, 2.0 mmol) was added, followed by ethanesulfonyl chloride (200 ⁇ L) and reacted for 30 minutes.
  • Example 3 Preparation of 1-ethanesulfonyl-2-(3-tert-butyl-4-(2-trimethylsilylethyl)-1H-pyrazol-1-yl)benzimidazole (Compound No. 2-6) 1-ethanesulfonyl-2-(3-tert-butyl-4-trimethylsilylethynyl-1H-pyrazol-1-yl)benzimidazole (0.11 g, 0.25 mmol) was dissolved in ethyl acetate (2.5 mL), 10% Palladium on carbon (0.02 g) was added and the reaction vessel was purged with hydrogen. After stirring at room temperature under normal pressure for 2 hours, the reaction solution was filtered through celite. After concentrating the filtrate, it was purified by column chromatography to obtain the desired product (0.22 g, melting point: 101-103°C, yield 80%).
  • Formulation example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above ingredients are uniformly mixed and dissolved to form an emulsion.
  • Formulation example 2 The compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to obtain powders.
  • Formulation example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignosulfonate 5 parts The above are uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to form granules.
  • Formulation example 4 Compound of the present invention 20 parts kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder.
  • Formulation example 5 The compound of the present invention 20 parts Polyoxyethylene lauryl ether 3 parts Sodium dioctylsulfosuccinate 3.5 parts Dimethyl sulfoxide 37 parts 2-propanol 36.5 parts The above are uniformly mixed and dissolved to prepare a water-soluble concentrate preparation.
  • Formulation example 6 The compound of the present invention 2 parts Dimethyl sulfoxide 10 parts 2-propanol 35 parts Acetone 53 parts The above ingredients are uniformly mixed and dissolved to prepare a liquid for spraying.
  • Formulation example 7 Compound of the present invention 5 parts Hexylene glycol 50 parts Isopropanol 45 parts The above are uniformly mixed and dissolved to prepare a solution for transdermal administration.
  • Formulation example 8 Compound of the present invention 5 parts Propylene glycol monomethyl ether 50 parts Dipropylene glycol 45 parts The above are uniformly mixed and dissolved to prepare a solution for transdermal administration.
  • Formulation example 9 2 parts of the compound of the present invention 98 parts of light liquid paraffin The above are uniformly mixed and dissolved to prepare a solution for percutaneous administration (dripping).
  • Formulation example 10 Compound of the present invention 2 parts Light liquid paraffin 58 parts Olive oil 30 parts ODO-H 9 parts Shin-Etsu Silicone 1 part The above ingredients are uniformly mixed and dissolved to prepare a solution for percutaneous administration (dripping).
  • Test example 1 Control value test against green peach aphid (Myzus persicae) Chinese cabbage was planted in a plastic pot of 8 cm in diameter and 8 cm in height to propagate green peach aphid, and the number of parasites in each pot was investigated.
  • the benzimidazole compound represented by the general formula (1) or general formula (1-1) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and the chemical solution is sprayed on the foliage of potted Chinese cabbage.
  • the pot After air-drying, the pot was stored in a greenhouse, and on the 6th day after spraying the chemical, the number of parasites of green peach aphids parasitic on each Chinese cabbage was investigated, and the control value was calculated from the following formula. determined according to
  • Ta Number of parasites before spraying in treated area
  • Ca Number of parasites before spraying in untreated area
  • C Number of parasites after spraying in untreated area
  • compound 1-1 of the compounds of the present invention showed an activity of D or higher.
  • Test example 2 Insecticidal test against Laodelphax striatella
  • the benzimidazole compound represented by the general formula (1) or general formula (1-1) of the present invention or a salt thereof is dispersed in water and diluted in a chemical solution of 500 ppm
  • Rice seedlings (cultivar: Nipponbare) were immersed for 30 seconds, air-dried, placed in a glass test tube, inoculated with 10 each of the 3rd instars of the planthopper planthopper, and then plugged with cotton. Then, the corrected mortality rate was calculated from the following formula and judged according to the following judgment criteria.
  • compound 2-1 of the compounds of the present invention showed an activity of D or higher.
  • Test example 3 Insecticidal test against diamondback moth (Plutella xylostella) Adults of diamondback moth were released to Chinese cabbage seedlings to lay eggs, and two days after release, the Chinese cabbage seedlings with laid eggs were treated with general formula (1) or general formula (1-) of the present invention.
  • the benzimidazole compound represented by 1) or a drug containing a salt thereof as an active ingredient was immersed in a chemical solution diluted to 500 ppm for about 30 seconds, air-dried, and allowed to stand in a constant temperature room at 25°C. After 6 days of immersion in the chemical solution, the number of hatched insects was investigated, and the corrected mortality rate was calculated according to the following formula. 1 ward 10 horses 3 consecutive system.
  • Test example 4 Acaricidal test against two-spotted spider mite (Tetranychus urticae).
  • Leaf discs with a diameter of 2 cm are prepared from kidney leaves, placed on moist filter paper, and inoculated with female adults, and then the benzimidazole compound represented by the general formula (1) or general formula (1-1) of the present invention.
  • 50 ml of a chemical solution containing a salt thereof as an active ingredient diluted to 500 ppm was evenly sprayed on a turntable, and after the spraying, it was allowed to stand in a constant temperature room at 25°C.
  • Two days after the chemical treatment the number of dead insects was investigated, the corrected mortality rate was calculated by the following formula, and judgment was made according to the judgment criteria of Test Example 2. 1 ward 10 horses 2 consecutive system.
  • Test example 5 Effect evaluation test on larval movement of Dirofilaria immitis 500 L-1 stage larvae of Dirofilaria immitis diluted in a predetermined preparation solution were inoculated in each hole of a 96-well plate, and the general formula (1) of the present invention ) or a DMSO-diluted solution of the benzimidazole compound represented by the general formula (1-1) or a salt thereof was added to a final concentration of 50 ppm. Then, it was left still for 3 days, and its exercise ability was investigated. Based on the inhibitory power of the DMSO solution alone, the motility inhibition rate of each treatment group was corrected and calculated, and judged according to the following criteria.
  • the compound of the present invention, 2-1 showed the activity of A.
  • Test example 6 Influence evaluation test on the development of Dirofilaria immitis A predetermined preparation solution, 8 to 20 L-3 stage larvae of Dirofilaria immitis and a DMSO diluted solution of the benzimidazole compound of the present invention were added to each hole of a 24-well plate. In addition, the final concentration was 50 ppm. Seven days later, the larvae that had grown to the L-4 stage were counted, and the growth inhibition rate from L3-stage larvae to L4-stage larvae was calculated.
  • the compounds represented by the general formula (1) or general formula (1-1) of the present invention showed a growth inhibition rate of 50% or more. rice field.
  • the compound according to the present invention has an excellent control effect against a wide range of agricultural and horticultural pests and mites, and is useful.

Abstract

Les insectes nuisibles, etc., provoquent toujours une détérioration significative sur la production de cultures agricoles et horticoles, etc. Dans ces circonstances, la présente invention aborde le problème du développement et de la fourniture d'un nouvel insecticide/acaricide agricole et horticole et d'un nouvel agent de lutte contre la filariose canine pour des animaux en tenant compte de facteurs tels que l'apparition d'insectes nuisibles résistants aux agents existants.　La présente invention concerne un composé de benzimidazole représenté par la formule générale (1) [dans laquelle : R représente un groupe alkyle, etc. ; Y1, Y2, Y3 et Y4 représentent un atome d'hydrogène, etc. ; X représente un groupe alkyle, un halogénoalcoxy, etc. ; R1, R2 et R3 représentent un groupe alkyle ; A représente un groupe alkylène, un groupe alcynylène, etc. ; et m représente 2] ou un sel associé, un insecticide/acaricide agricole et horticole et un agent de lutte contre la filariose canine pour animaux, chacun le comprenant en tant que principe actif, son procédé d'utilisation, etc.
PCT/JP2022/022543 2021-06-02 2022-06-02 Composé de benzimidazole ou sel associé, insecticide/acaricide agricole et horticole et agent de lutte contre la filariose canine pour animaux le contenant, et son procédé d'utilisation WO2022255465A1 (fr)

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Citations (6)

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JPS488939A (fr) * 1971-06-18 1973-02-03
US6211177B1 (en) * 1998-11-24 2001-04-03 Cell Pathways, Inc. Method for treating neoplasia by exposure to substituted 2-aryl-benzimidazole derivatives
WO2012050141A1 (fr) * 2010-10-14 2012-04-19 住友化学株式会社 Composé à noyau hétéroaromatique et son utilisation pour la lutte contre les organismes nuisibles
WO2019122319A1 (fr) * 2017-12-21 2019-06-27 Bayer Aktiengesellschaft Silylméthylhétéroaryloxyquinoléines trisubstitués et analogues
WO2021107113A1 (fr) * 2019-11-28 2021-06-03 日本農薬株式会社 Composé de benzimidazole ou sels de celui-ci, insecticide/acaricide agricole et horticole contenant ledit composé, et procédé d'utilisation associé
WO2021107110A1 (fr) * 2019-11-28 2021-06-03 日本農薬株式会社 Composé benzimidazole ou son sel, agent insecticide et acaricide agricole et horticole contenant ledit composé, et procédé d'utilisation dudit agent insecticide et acaricide

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Publication number Priority date Publication date Assignee Title
JPS488939A (fr) * 1971-06-18 1973-02-03
US6211177B1 (en) * 1998-11-24 2001-04-03 Cell Pathways, Inc. Method for treating neoplasia by exposure to substituted 2-aryl-benzimidazole derivatives
WO2012050141A1 (fr) * 2010-10-14 2012-04-19 住友化学株式会社 Composé à noyau hétéroaromatique et son utilisation pour la lutte contre les organismes nuisibles
WO2019122319A1 (fr) * 2017-12-21 2019-06-27 Bayer Aktiengesellschaft Silylméthylhétéroaryloxyquinoléines trisubstitués et analogues
WO2021107113A1 (fr) * 2019-11-28 2021-06-03 日本農薬株式会社 Composé de benzimidazole ou sels de celui-ci, insecticide/acaricide agricole et horticole contenant ledit composé, et procédé d'utilisation associé
WO2021107110A1 (fr) * 2019-11-28 2021-06-03 日本農薬株式会社 Composé benzimidazole ou son sel, agent insecticide et acaricide agricole et horticole contenant ledit composé, et procédé d'utilisation dudit agent insecticide et acaricide

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SHI HAIBIN, TICE COLIN M., EMERT-SEDLAK LORI, CHEN LI, LI WING FAI, CARLSEN MARIANNE, WROBEL JAY E., REITZ ALLEN B., SMITHGALL THO: "Tight-Binding Hydroxypyrazole HIV-1 Nef Inhibitors Suppress Viral Replication in Donor Mononuclear Cells and Reverse Nef-Mediated MHC-I Downregulation", ACS INFECTIOUS DISEASES, vol. 6, no. 2, 14 February 2020 (2020-02-14), US , pages 302 - 312, XP055924686, ISSN: 2373-8227, DOI: 10.1021/acsinfecdis.9b00382 *

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