WO2016125621A1 - Composé benzimidazole, et application de celui-ci pour lutter contre les arthropodes nuisibles - Google Patents

Composé benzimidazole, et application de celui-ci pour lutter contre les arthropodes nuisibles Download PDF

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WO2016125621A1
WO2016125621A1 PCT/JP2016/052090 JP2016052090W WO2016125621A1 WO 2016125621 A1 WO2016125621 A1 WO 2016125621A1 JP 2016052090 W JP2016052090 W JP 2016052090W WO 2016125621 A1 WO2016125621 A1 WO 2016125621A1
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group
compound
hydrogen atom
alkyl group
atom
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舞衣 伊藤
中嶋　祐二
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住友化学株式会社
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

Definitions

  • the present invention relates to a benzimidazole compound and its use for controlling harmful arthropods.
  • An object of the present invention is to provide a compound having an excellent control effect against harmful arthropods.
  • the present inventors have found that the benzimidazole compound represented by the following formula (I) has an excellent controlling effect on harmful arthropods, leading to the present invention. .
  • A represents a nitrogen atom or CR 6
  • R A and R B represents —OSO 2 CF 3
  • the other represents a hydrogen atom
  • R 1 represents a C1-C4 alkyl group, a cyclopropyl group or a cyclopropylmethyl group
  • R 2 represents a hydrogen atom, a C1-C4 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a (C1-C3 alkoxy) C1-C3 alkyl group
  • R 3 and R 4 each independently represents a hydrogen atom or a halogen atom
  • R 5 and R 6 each independently represents a hydrogen atom
  • —S (O) m R 7 ⁇ m represents 0, 1, or 2.
  • C3-C6 cycloalkyl group optionally having one or more halogen atoms, (C1-C6 alkoxy) optionally having one or more halogen atoms, C1-C6 alkyl group having one or more halogen atoms (C3-C6 cycloalkyl) C1-C6 alkyl group, —R 8 , —OR 8 , —NR 9 R 10 , —C (O) R 11 , —COOR 11 , —C (O) NR 9 R 10 , a phenyl group optionally having one or more atoms or substituents selected from group X, a 5- to 6-membered heteroaryl group optionally having one or more atoms or substituents selected from group X ⁇
  • the atoms and substituents may be the same or different.
  • R 11 and R 13 each independently represents a hydrogen atom or a C1-C6 alkyl group which may have one or more halogen atoms. ] (Hereinafter, the compound represented by the formula (I) may be referred to as the present compound).
  • R 1 is a C1-C3 alkyl group
  • R 2 is a hydrogen atom, a C1-C3 alkyl group, a propargyl group, or a (C1-C3 alkoxy) C1-C3 alkyl group
  • R 5 and R 6 are each independently one or more selected from a hydrogen atom, —R 7 , —S (O) m R 7 , —OR 7 , —NR 9 R 10 , —COOR 7 , group
  • An optionally substituted 5- to 6-membered heteroaryl group, a halogen atom, —NR 11 C (O) R 7 , —NR 11 CO 2 R 7 , —NR 11 (OR 7 ), or —N benzimidazole compound according to S (O) is a p R 7 R 12 [1] .
  • R A is —OSO 2 CF 3 and R B is a hydrogen atom.
  • R 1 is an ethyl group
  • R 2 is a hydrogen atom, a C1-C3 alkyl group, a propargyl group, or a (C1-C3 alkoxy) C1-C3 alkyl group
  • R 3 and R 4 are hydrogen atoms
  • R 5 is a hydrogen atom, a halogen atom, a C1-C3 alkyl group that may have one or more halogen atoms, or a C1-C3 alkoxy group that may have one or more halogen atoms
  • R 6 is a hydrogen atom or a halogen atom.
  • a harmful arthropod control agent comprising the benzimidazole compound according to any one of [1] to [6] and an inert carrier.
  • a method for controlling harmful arthropods which comprises applying an effective amount of the benzimidazole compound according to any one of [1] to [6] to harmful arthropods or their habitat.
  • the compound of the present invention has excellent control activity against harmful arthropods.
  • C1-C4 means that the number of carbon atoms is 1 to 4.
  • C1-C6 chain hydrocarbon group means a C1-C6 alkyl group, a C2-C6 alkenyl group, and a C2-C6 alkynyl group.
  • a halogen atom is a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • Examples of the C1-C6 alkyl group optionally having one or more halogen atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a hexyl group, a fluoromethyl group, a trifluoromethyl group, a chlorodifluoromethyl group, Examples include 2-bromoethyl group, 1,1-difluoroethyl group, 2,2,2-trifluoroethyl group, and pentafluoroethyl group.
  • Examples of the C2-C6 alkenyl group which may have one or more halogen atoms include a vinyl group, an allyl group, a 3-methyl-2-butenyl group, a 2,2-dichlorovinyl group, and a 1,1-difluoroallyl group. Groups and pentafluoroallyl groups.
  • Examples of the C2-C6 alkynyl group which may have one or more halogen atoms include ethynyl group, 1-propynyl group, 2-propynyl group, chloroethynyl group, 1-bromo-2-hexynyl group and 1- ( A trifluoro) -2-butynyl group.
  • Examples of the C3-C6 cycloalkyl group optionally having one or more halogen atoms include a cyclopropyl group, a 1-fluorocyclopropyl group, a 2,2-dichlorocyclopropyl group, and a 3,3-dibromocyclobutyl group. And a cyclohexyl group.
  • the (C1-C6 alkoxy) C1-C6 alkyl group which may have one or more halogen atoms means that the C1-C6 alkoxy group which may have one or more halogen atoms has one or more halogen atoms Means a group bonded to an optionally substituted C1-C6 alkyl group, and examples thereof include a methoxymethyl group, an ethoxymethyl group, a 1- (trifluoromethoxy) ethyl group, and a 3-fluoro-6- (hexyloxy) hexyl group. It is done.
  • the (C3-C6 cycloalkyl) C1-C6 alkyl group which may have one or more halogen atoms is a C1-C6 cycloalkyl group which may have one or more halogen atoms.
  • Examples of the C2-C6 alkanediyl group which may have one or more halogen atoms include ethane-1,2-diyl group, 2,2,3,3-tetrafluorobutane-1,4-diyl group, Examples include pentane-2,5-diyl group, 3- (trifluoromethyl) pentane-1,5-diyl group, and hexane-1,6-diyl group.
  • the 5- to 6-membered heteroaryl group means, for example, a 5- or 6-membered aromatic heterocyclic group containing up to 3 atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • R 1 is a C1-C4 alkyl group
  • R 2 is a hydrogen atom, a methyl group, a propargyl group or a methoxymethyl group
  • R 5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 5- to 6-membered hetero atom optionally having one or more atoms or substituents selected from group X
  • Aspect 4-1 The compound according to Aspect 3, wherein R 5 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • Aspect 4-2 A compound according to Aspect 3, wherein R 2 is a hydrogen atom or a methyl group, and R 5 is a hydrogen atom or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 1 is a C1-C4 alkyl group
  • R 2 is a hydrogen atom, a methyl group, a propargyl group or a methoxymethyl group
  • R 5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 5- to 6-membered hetero atom optionally having one or more atoms or substituents selected from group X
  • Aspect 7-1 The compound according to Aspect 6, wherein R 5 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 2 is a hydrogen atom or a methyl group
  • R 5 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 1 is a C1-C4 alkyl group
  • R 2 is a hydrogen atom, a methyl group, a propargyl group or a methoxymethyl group
  • R 5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 5- to 6-membered hetero atom optionally having one or more atoms or substituents selected from group X
  • R 1 is a C1-C4 alkyl group
  • R 2 is a hydrogen atom, a methyl group, a propargyl group or a methoxymethyl group
  • R 5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 5- to 6-membered hetero atom optionally having one or more atoms or substituents selected from group X
  • Aspect 14-1 The compound according to Aspect 13, wherein R 5 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 2 is a hydrogen atom or a methyl group
  • R 5 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or 1 , 2,4-Triazolyl group.
  • R A is —OSO 2 CF 3
  • R B is a hydrogen atom
  • A is a nitrogen atom
  • R 1 is a C1-C4 alkyl group
  • R 2 is hydrogen.
  • R 3 and R 4 are hydrogen atoms
  • R 5 is a hydrogen atom, and has one or more halogen atoms
  • R A is —OSO 2 CF 3
  • R B is a hydrogen atom
  • A is CR 6
  • R 1 is a C1-C4 alkyl group
  • R 2 is hydrogen An atom, a C1-C3 alkyl group, a propargyl group or a (C1-C3 alkoxy) C1-C3 alkyl group
  • R 3 and R 4 are hydrogen atoms
  • R 5 is a hydrogen atom, a halogen atom or one or more halogen atoms
  • R A is a hydrogen atom
  • R B is —OSO 2 CF 3
  • A is a nitrogen atom
  • R 1 is a C1-C4 alkyl group
  • R 2 is hydrogen An atom, a C1-C3 alkyl group, a propargyl group or a (C1-C3 alkoxy) C1-C3 alkyl group
  • R 3 and R 4 are hydrogen atoms
  • R 5 is a hydrogen atom, a halogen atom or one or more halogen atoms
  • R 1 is a C1-C4 alkyl group
  • R 2 is a C1-C3 alkyl group or a hydrogen atom
  • R 5 may have one or more halogen atoms.
  • the compound of the present invention can be produced, for example, according to the methods described in the following production methods 1 to 7 and reference production methods 1 to 4.
  • the compound represented by the formula (Inn1) (hereinafter also referred to as the compound (Inn1)) is the same as the compound represented by the formula (Inn0) (hereinafter referred to as the compound (Inn0)).
  • the reaction is usually performed in a solvent.
  • the solvent include halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene (hereinafter referred to as halogenated hydrocarbons), nitriles such as acetonitrile (hereinafter referred to as nitriles), and alcohols such as methanol and ethanol.
  • esters such as ethyl acetate and butyl acetate (hereinafter referred to as esters), acetic acid, water, and mixtures thereof.
  • the oxidizing agent include peracetic acid, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and aqueous hydrogen peroxide.
  • mCPBA m-chloroperbenzoic acid
  • a base or a catalyst may be added as necessary.
  • the base used for the reaction include sodium carbonate.
  • the catalyst used for the reaction include tungstic acid and sodium tungstate.
  • the oxidizing agent is usually used at a ratio of 1 to 1.2 mol.
  • the base is generally used in an amount of 0.01 to 1 mol per 1 mol of the compound (In0).
  • the catalyst is generally used in an amount of 0.01 to 0.5 mol per 1 mol of the compound (In0).
  • the reaction temperature is usually in the range of ⁇ 50 to 50 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound represented by the formula (In2) (hereinafter also referred to as the compound (Inn2)) is the same as the compound represented by the formula (In3) (hereinafter referred to as the compound (Inn3)).
  • r represents 0 or 1, and other symbols have the same meaning as described above.
  • compound (In3) is used in place of compound (In0), and the oxidizing agent is 2 to 10 mol when r is 0 with respect to 1 mol of compound (In3), and r is 1
  • compound (In2) can be obtained according to the method described in Production Method 1 using 1 to 10 moles.
  • the compound of the present invention represented by formula (I) (hereinafter also referred to as compound (I)) is composed of a compound represented by formula (M1) (hereinafter also referred to as compound (M1)) and a compound represented by formula (M2) ( Hereinafter, it can be produced by reacting with the compound (M2)) in the presence of a condensing agent. [Wherein the symbols have the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran (hereinafter referred to as THF), tert-butyl methyl ether (hereinafter referred to as MTBE) (hereinafter referred to as ether).
  • THF tetrahydrofuran
  • MTBE tert-butyl methyl ether
  • Halogenated hydrocarbons aromatic hydrocarbons such as toluene, benzene and xylene (hereinafter referred to as aromatic hydrocarbons), esters, nitriles, aprotic polar solvents, pyridine, quinoline And nitrogen-containing aromatic compounds (hereinafter referred to as nitrogen-containing aromatic compounds) and mixtures thereof.
  • Examples of the condensing agent used in the reaction include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as EDCI hydrochloride) and 1,3-dicyclohexylcarbodiimide. .
  • This reaction can also be performed by adding a catalyst as needed.
  • Examples of the catalyst used in the reaction include 1-hydroxybenzotriazole.
  • the compound (M2) is usually 0.5 to 2 mol
  • the condensing agent is usually 1 to 5 mol
  • the catalyst is usually 0.01 to 1 mol with respect to 1 mol of the compound (M1). Used in proportions.
  • the reaction temperature of the reaction is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M2) can be produced according to the method described in International Publication No. 2012/088684 or International Publication No. 2013/018928.
  • Compound (I) can be produced by dehydrating a compound represented by formula (M3) (hereinafter referred to as compound (M3)). [Wherein the symbols have the same meaning as described above. ]
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers, halogenated hydrocarbons, aromatic hydrocarbons, esters, nitriles, aprotic polar solvents, nitrogen-containing aromatic compounds, and mixtures thereof.
  • a condensing agent or an acid can be used as necessary.
  • the condensing agent used in the reaction include acetic anhydride, trifluoroacetic anhydride, and EDCI hydrochloride.
  • Examples of the acid used in the reaction include sulfonic acids such as p-toluenesulfonic acid, carboxylic acids such as acetic acid, polyphosphoric acid, and the like.
  • the condensing agent when a condensing agent is used, the condensing agent is usually used in a proportion of 1 to 5 mol, and when an acid is used, the acid is usually used in a proportion of 0.1 to 5 mol. It is done.
  • the reaction temperature of the reaction is usually in the range of 0 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (I) can be produced by reacting compound (M1) with a compound represented by formula (M4) (hereinafter referred to as compound (M4)). [Wherein the symbols have the same meaning as described above. ]
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, esters, nitriles, aprotic polar solvents, and mixtures thereof.
  • This reaction can also be performed by adding a base as necessary.
  • the base used for the reaction include alkali metal carbonates, tertiary amines such as triethylamine, and nitrogen-containing aromatic compounds.
  • the compound (M4) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
  • the reaction temperature of the reaction is usually in the range of 20 to 200 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M4) can be produced according to the method described in International Publication No. 2012/088684 or International Publication No. 2013/018928.
  • Compound (I) is a compound of formula (M5) (hereinafter referred to as compound (M5)) and a compound of formula (M6) (hereinafter referred to as compound (M6)) of sodium dithionite. It can manufacture by making it react in presence. [Wherein the symbols have the same meaning as described above. ] The reaction is carried out according to the methods described in Synthesis, 1, 47-56 (2005), or their methods. Examples of the solvent used in the reaction include alcohols, aprotic polar solvents, water, and mixtures thereof.
  • the compound (M6) is usually used in a proportion of 1 to 1.5 mol, and sodium dithionite is usually used in a proportion of 3 to 5 mol.
  • the reaction temperature of the reaction is usually in the range of 50 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M6) can be produced according to the method described in International Publication No. 2012/088684 or International Publication No. 2013/018928.
  • a compound represented by formula (Ic) (hereinafter referred to as compound (Ic)) is represented by a compound represented by formula (I-NH) (hereinafter referred to as compound (I-NH)).
  • a compound represented by the formula (M7) (hereinafter referred to as compound (M7)) in the presence of a base.
  • R 2c represents a C1-C4 chain hydrocarbon group, a C3-C6 cycloalkyl group, or a (C1-C3 alkoxy) C1-C3 alkyl group
  • L represents a chlorine atom, a bromine atom, an iodine atom
  • It represents a leaving group such as a fluoromethylsulfonyloxy group and a methylsulfonyloxy group, and other symbols have the same meaning as described above.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers, aromatic hydrocarbons, nitriles, aprotic polar solvents, and mixtures thereof.
  • Examples of the base used in the reaction include alkali metal or alkaline earth metal hydrides such as sodium hydride, potassium hydride and calcium hydride, alkali metal carbonates, tertiary amines, potassium tert-butoxide and the like. Can be mentioned.
  • compound (M7) is usually used in a proportion of 0.8 to 1.5 mol, and base is usually used in a proportion of 0.8 to 1.5 mol with respect to 1 mol of compound (I-NH). Used.
  • the reaction temperature is usually in the range of ⁇ 20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (M7) is a known compound or can be produced from a known compound.
  • Reference manufacturing method 1 Compound (M1) can be produced by reducing compound (M5).
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include ethers, alcohols, esters, acetic acid, water, and mixtures thereof.
  • the reducing agent used in the reaction include iron.
  • an acid can be used as necessary.
  • the acid used for the reaction include acetic acid and hydrochloric acid.
  • the reducing agent is usually used in a proportion of 3 to 10 mol per 1 mol of the compound (M5).
  • the reaction temperature of the reaction is usually in the range of 20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • a compound represented by formula (M5-NH) (hereinafter referred to as compound (M5-NH)) is produced from a compound represented by formula (M8) (hereinafter referred to as compound (M8)).
  • a compound represented by formula (M5-c) (hereinafter referred to as compound (M5-c)) can be produced from compound (M8). [Wherein, one of R D and R E represents a hydroxyl group, the other represents a hydrogen atom, and the other symbols represent the same meaning as described above. ] First, the process for producing the compound (M5-NH) from the compound (M8) will be described.
  • the reaction can be produced by reacting the compound (M8) with trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include ethers, aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons, esters, nitriles, aprotic polar solvents, and mixtures thereof.
  • Examples of the base used for the reaction include tertiary amines.
  • trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride is usually used at a ratio of 0.8 to 1.5 mol with respect to 1 mol of the compound (M8).
  • the reaction temperature is usually in the range of ⁇ 78 to 50 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • compound (M5-c) can be produced according to the method described in production method 7, using compound (M5-NH) instead of compound (1-NH).
  • Reference manufacturing method 3 Compound (M3) can be produced by reacting compound (M1) and compound (M2) in the presence of a condensing agent or an acid. [Wherein the symbols have the same meaning as described above. ] This reaction can be carried out according to the method described in Production Method 3.
  • Reference production method 4 Compound (M3) can be produced by reacting compound (M1) with compound (M4). [Wherein the symbols have the same meaning as described above. ] The reaction can be carried out according to the method described in Production Method 5.
  • the reaction mixture is poured into water and extracted with an organic solvent, and the organic layer is concentrated; the reaction mixture is poured into water.
  • the resulting solid is collected by filtration; or by performing post-treatment operations such as collecting the solid produced in the reaction mixture by filtration, the compound of the present invention, compound (M5), compound (M5-NH), compound ( M5-c) or compound (M3) can be isolated.
  • the isolated compound of the present invention, compound (M5), compound (M5-NH), compound (M5-c) or compound (M3) can be further purified by recrystallization, chromatography or the like.
  • Me means a methyl group
  • Tr means a 1,2,4-triazol-1-yl group
  • Pz means a pyrazol-1-yl group.
  • [A; R 5 ; n] [CH; H; 0], [CH; H; 1], [CH; H; 2], [CH; F; 0], [CH; F; 1], [ CH; F; 2], [CH; Cl; 0], [CH; Cl; 1], [CH; Cl; 2], [CH; Br; 0], [CH; Br; 1], [CH; Br; 2], [CH; Me; 0], [CH; Me; 1], [CH; Me; 2], [CH; CF 3 ; 0], [CH; CF 3 ; 1], [CH; CF 3 ; 2], [CH; CF 2 CF 3 ; 0], [CH; CF 2 CF 3 ; 1], [CH; CF 2 CF 3 ; 2], [CH; CF 2 CF 3 ; 1], [CH; CF 2 CF 3 ; 2], [CH; OMe; 0], [CH; OMe; 1], [CH; OMe; 2], [CH; OCF 3 ;
  • [A; R 5 ; n] [CH; F; 0], [CH; F; 1], [CH; F; 2], [CH; Cl; 0], [CH; Cl; 1], [ CH; Cl; 2], [CH; Br; 0], [CH; Br; 1], [CH; Br; 2], [CH; Me; 0], [CH; Me; 1], [CH; Me; 2], [CH; CF 3 ; 0], [CH; CF 3 ; 1], [CH; CF 3 ; 2], [CH; CF 2 CF 3 ; 0], [CH; CF 2 CF 3 ; 1], [CH; CF 2 CF 3 ; 2], [CH; OMe; 0], [CH; OMe; 1], [CH; OMe; 2], [CH; OCF 3 ; 0], [CH ; OCF 3 ; 1], [CH; OCF 3 ; 2], [CH; SCF 3 ; 0], [CH; SCF 3 ; 1], [CH; S
  • [A; R 5 ; n] [CH; F; 0], [CH; F; 1], [CH; F; 2], [CH; Cl; 0], [CH; Cl; 1], [ CH; Cl; 2], [CH; Br; 0], [CH; Br; 1], [CH; Br; 2], [CH; Me; 0], [CH; Me; 1], [CH; Me; 2], [CH; CF 3 ; 0], [CH; CF 3 ; 1], [CH; CF 3 ; 2], [CH; CF 2 CF 3 ; 0], [CH; CF 2 CF 3 ; 1], [CH; CF 2 CF 3 ; 2], [CH; OMe; 0], [CH; OMe; 1], [CH; OMe; 2], [CH; OCF 3 ; 0], [CH ; OCF 3 ; 1], [CH; OCF 3 ; 2], [CH; SCF 3 ; 0], [CH; SCF 3 ; 1], [CH; S
  • pests for which the compounds of the present invention are effective include harmful animals such as harmful insects and harmful mites.
  • harmful animals include, but are not limited to, the following.
  • Hemiptera pests Japanese green planthopper (Laodelphax striatellus), Japanese green planthopper (Nilaparvata lugens), white planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), etc .; (Nephotettix nigropictus), Incospider (Recilia dorsalis), Emporasca onukii, Empoasca fabae, Cornleaf Hopper (Dalbulus maidis), White-leafed beetle Mahanarva posticata, Mahanarva fimbriolata, etc .; Aphis goss ii, Aphis spiraecola, Myzus persicae, Japanese radish aphid (Br evicoryne brassicae), lipstick aphid (Lipaphis erysimi), tulip beetle aphid (Macrosiphum euphorbiae), potato beet
  • Lepidopterous insects Chilo ⁇ suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cai halopatia cis (Marasmia exigua), cotton moth (Notarcha derogata), green eel (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), yellow moth (Hellula undalis), Shibatatsuga (Pediasia teterum (Pediasia teterum) Diatraea saccharalis), etc .; Sorgoptera ⁇ ⁇ litura, Spodoptera imexnagua, Spodoptera imexna rata), mushroom (Mamestra brassicae), rice mushroom (Sesamia inferens), white-footed mushroom (Spodoptera mauritia), frangipaya (Narang
  • Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis) and other moths; White butterflies such as Pieris rapae; Nasihimeshinmoi (Grapholita molesta), Sumohimeshini (Grapholita dimorph) a), leguminous moth (Leguminivora ⁇ glycinivorella), Azuki beetle (Matsumuraeses azukivora), apple wolfberry (Adoxophyes orana fasciata), tea wolfberry (Adoxophyes honmai), chamonaki (Homona magnancos), (Cydia pomonella), Tetramoera schistaceana, Bean Shoot Borer (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana), etc .; Sinkigas (Carposina sasakii); Coffee Leaf miner (Leucoptera coffeela), A
  • Citrus thrips (Frankliniella occidentalis), Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Thrips tabaci, Thrips tabaci, Thrips tabaci, Thrips tabaci, Thrips tabaci Thrips: The Thrips such as Haplothrips aculeatus.
  • Diptera insect fly, Delia platura, Delia qua antiqua, etc .; sugar beet root maggot (Tetanops myopaeformis), etc .; (Liriomyza trifolii), leafhoppers (Chromatomyia horticola), etc .; leafhoppers (Chlorops oryzae); Fruit flies such as Ceratitis capitata; sand flies such as Hydrellia griseola, Hydrellia philippina, Hydrellia sasakii; Drosophila; flies such as Megaselia spiracularis; flies such as Clogmia albipunctata; black fly flies; Mayetiola destructor; Streptococcus such as Diopsis macrophthalma; Crane fly such as European ⁇ cranefly (Tipula palracosa), Common cranefly (Tipula oleracea), European cranefly (Tipula palud
  • Coleoptera Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cumber rot balte (ab) , Cucurbit Beetle (Diabrotica speciosa), Bean Leaf Beetle (Cerotoma trifurcata), Bark beetle Beetle (Oulema melanopus), Root beetle (Aulacophora femoralis), Kibushi horn beetle (Phyllotreta striolata), Colorado potato beetle (De , Grapes colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera)
  • Insect pests Locusta migratoria,ixie grasshopper (Dociostaurus maroccanus), Australian grasshopper (Chortoicetes terminifera), red locust (Nomadacris septemfasciata), Brown Locust (Locustana parust Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Grasshoppers such as Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris ⁇ guttulosa), Cobaineago (Oxya yezoensis), Red-tailed hawk (Oxya japonica), Thai winged chinook (Patanga succincta); Kellys such as ryllotalpa
  • Hymenopteran pests bees such as Athalia rosae and Athalia japonica; fire ants; ants such as Brown leaf-cutting ant (Atta capiguara)
  • Cockroach insects German cockroaches such as the German cockroach (Blattella germanica); cockroaches such as the black cockroach (Periplaneta fuliginosa), the American cockroach (Periplaneta americana), the black cockroach (Periplaneta brunnea), and the American cockroach (Blatta orientalis).
  • Termite pests Yamato termites (Reticulitermes speratus), termites (Coptotermes formosanus), American ants termites (Incisitermes minor), stag termites (Cryptotermes domesticus), ants, termites (Odontotermes eoformosaterm), ants Glyptotermes Reticulitermes kanmonensis), Takasago termites (Nasutitermes takasagoensis), Nitobe termites (Pericapritermes nitobei), Mushy termites (Sinocapritermes mushae), Cornitermes cumulans like.
  • Mites Spider mites (Tetranychus urticae), spider mites (Tetranychus kanzawai), red spider mites (Panonychus ulmi), apple spider mites (Panonychus ulmi), spider mites (Aculops pelekassi), red mite Pistrum (copper) Tomato rustic mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese radish mites (Acaphylla theavagrans), Green rustic mites (Eriophyes chibaensis), Apple ticks (Aculus Mattendali), etc .; Toad spider mites (Brevipalpus phoenicis) and other spider mites; Toxid spider mites (Haemaphysalis longicornis), tossed tick (Haemaphysalis flava), tortoise tick (Dermacentor taiwanens
  • Tick such as: Tyrophagus putrescentiae, spiny mite (Tyrophagus similis), etc .; mite mite (Dermatophagoides pteronyssinus); , Mites (Cheyletus moorei), crayfish mites (Cheyletiella yasguri); mite mites (Otodectes cynotis), mite mites (Sarcoptes scabiei), etc .; Acne mites such as emodex canis; Carp mites; House crabs; Hornets such as Ornithonyssus sylviarum; Etc.
  • Spiders Common spiders such as Cheracanthium japonicum; Brown spiders such as Latrodectus hasseltii.
  • Lip and leg class Geges such as Gezi (Thereuonema hilgendorfi); Barley pods such as Scolopendra subspinipes.
  • Double-legged class zelkova (Oxidus gracilis), zelkova (Nedyopus tambanus), etc.
  • Isopods Rubber beetles such as Armadillidium vulgare.
  • Gastropoda Coleoptera such as Limax marginatus and Limax flavus; Apple mussels such as Pomacea canaliculata; Monoaragai such as Austropeplea ollula.
  • Nematodes Aphelenchoides besseyi, such as Aphelenchoides besseyi; Minaminegusaresenchu (Pratylenchus coffeae), Pratylenchus brachyurus, Pratylenchus neglectus ⁇ , Radsimus Cucumber species: Javaloid nematode Me (Meloidogyne javanica), Sweet potato nematode Me (Meloidogyne incognita), Kitaenbu nematode Me (Meloidogyne hapla), soybean cyst nematode (Heterodera glycines), potato cyst nematode (Globodera Heterodera; Hopro-Rimes such as Rotylenchulus reniformis; Anguinas such as Nothotylenchus acris and Ditylenchus dipsaci; Tirenkurusu such as Luz Semi penetrometer transformer (Tylenchulus semipen
  • the target harmful insects and harmful ticks may be insects and ticks that have reduced drug sensitivity to insecticides / acaricides or have developed drug resistance.
  • the drug sensitivity is greatly reduced or the drug resistance is greatly developed, it is desirable to use the composition of the present invention containing an insecticide / acaricide other than the target insecticide / acaricide.
  • the compounds of the present invention can also be used to protect plants from plant diseases caused by insect-borne viruses.
  • Examples of plant diseases caused by insect-borne viruses having the control effect of the compound of the present invention include the following.
  • Rice dwarf disease (Rice waika virus), Tundra disease (Rice tungro spherical virus, Rice tungro bacilliform virus), Rice grassy stunt disease, Rice ragged stunt virus, Rice striped leaf blight Diseases (Rice stripe virus), rice black streaked dwarf virus, rice southern black-streaked dwarf virus, rice gall dwarf virus, rice leaf blight ( Rice hoja blanca virus), White leaf desease of rice, Yellow dwarf virus, Red disease (Rice penyakit merah virus), Rice yellow stunt virus, Transition yellowing Disease (Rice transitory yellowing virus), Rice yellow mottle virus, Rice necrosis mosaic virus, Rice dwarf stunt virus, North wheat mosaic disease Northern Cereal Mosaic Virus), barley yellowing atrophy disease (Barley Yellow Dwarf Virus), wheat yellow leaves disease (Wheat yellow dwarf virus), Oat sterile dwarf (Oat sterile dwarf virus), Wheat streak mosaic (Wheat streak mosaic virus) Maize dwarf mosaic virus, Maize stripe disease (maize stripe tenuivirus), Maize chlorotic
  • the harmful arthropod control agent of the present invention contains the compound of the present invention and an inert carrier.
  • the harmful arthropod control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and if necessary, a surfactant and other adjuvants for formulation.
  • the harmful arthropod control agent of the present invention can be mixed with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists.
  • the harmful arthropod control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur).
  • Polyester resins such as polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), n
  • DMF dimethylformamide
  • halogenated hydrocarbons diichloromethane, trichloroethane, carbon tetrachloride, etc.
  • sulfoxides dimethylsulfoxide, etc.
  • propylene carbonate and vegetable oil Soybean oil, cottonseed oil, etc.
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • fixing agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (is
  • the base material of the resin preparation examples include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string.
  • These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
  • the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid.
  • antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid
  • preservatives such as dehydroacetic acid.
  • Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.
  • an effective amount of the compound of the present invention is applied directly to harmful arthropods and / or to the place where the harmful arthropods live (plants, soil, households, animal bodies, etc.). Is done.
  • the harmful arthropod control method of the present invention is usually used in the form of the harmful arthropod control agent of the present invention.
  • the application amount is usually 1 to 10,000 g as the amount of the compound of the present invention per 10,000 m 2 .
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the compound of the present invention becomes 0.01 to 10,000 ppm. Applied, granules, powders, etc. are usually applied as they are.
  • These preparations and water dilutions of these preparations may be sprayed directly on harmful arthropods or plants such as crops to be protected from harmful arthropods, and harmful arthropods that inhabit the soil of cultivated land. You may treat to this soil in order to control.
  • it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
  • the amount applied is usually the amount of the compound of the present invention per 1 m 2 of treatment area when treated on the surface. 0.01 to 1000 mg, and when processing in a space, the amount of the compound of the present invention per 1 m 3 of the processing space is usually 0.01 to 500 mg.
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, wettable powder, flowable agent, etc., it is usually diluted with water so that the concentration of the compound of the present invention is 0.1 to 10,000 ppm. Apply oils, aerosols, smoke, poison baits, etc. as they are.
  • the harmful arthropod control agent of the present invention When used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals.
  • systemic suppression for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag.
  • the amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
  • room temperature usually indicates 10 to 30 ° C.
  • 1 H NMR represents a proton nuclear magnetic resonance spectrum
  • tetramethylsilane was used as an internal standard substance
  • chemical shift ( ⁇ ) was expressed in ppm.
  • a part represents a weight part.
  • Formulation Example 1 10 parts of any one of compounds 1 to 19 are dissolved in a mixture of 35 parts of xylene and 35 parts of DMF, to which 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed. Each formulation is obtained.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are added, and 20 parts of any one of compounds 1 to 19 are added and mixed to each water. Get a glaze.
  • Formulation Example 4 1 part of any one of compounds 1 to 19 is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic silicon hydroxide fine powder, 0.3 part of isopropyl acid phosphate and 93.7 parts of fusami clay are added and sufficiently stirred. Mix and evaporate off the acetone to obtain each powder.
  • Formulation Example 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 10 parts of any one of compounds 1 to 19 and 55 parts of water are mixed and finely divided by a wet pulverization method. Each flowable agent is obtained by grinding.
  • Formulation Example 6 0.1 part of any one of compounds 1 to 19 is dissolved in a mixture of 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of kerosene to obtain each oil.
  • Formulation Example 7 10 mg of any one of Compounds 1 to 19 is dissolved in 0.5 mL of acetone, and this solution is added dropwise to 5 g of animal solid feed powder (solid feed powder CE-2 for breeding and breeding, a product of Nippon Claire Co., Ltd.) Mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder solid feed powder CE-2 for breeding and breeding, a product of Nippon Claire Co., Ltd.
  • Formulation Example 8 0.1 part of any one of compounds 1 to 19 and 49.9 parts of neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled and shaken. Finally, an oil aerosol is obtained by mounting the actuator.
  • Formulation Example 9 0.6 part of any one of compounds 1 to 19, 0.01 part of BHT (2,6-di-tert-butyl-4-methylphenol), 5 parts of xylene, 3.39 parts of kerosene and an emulsifier ⁇ Rheidol MO -60 (manufactured by Kao Corporation) ⁇ 1 part mixed and 50 parts distilled water are filled into an aerosol container, and after the valve is mounted, 40 parts of propellant (LPG) is pressure filled through the valve. To obtain an aqueous aerosol.
  • BHT 2,6-di-tert-butyl-4-methylphenol
  • Formulation Example 10 0.1 g of any one of compounds 1 to 19 is mixed with 2 mL of propylene glycol and impregnated into a porous ceramic plate of 4.0 ⁇ 4.0 cm and a thickness of 1.2 cm to obtain a heating smoke. .
  • Formulation Example 11 5 parts of any one of compounds 1 to 19 and 95 parts of an ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT (registered trademark) WD301, manufactured by Sumitomo Chemical)
  • the mixture is melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extruder through a molding die to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm.
  • Formulation Example 12 5 parts of any one of compounds 1 to 19 and 95 parts of a soft vinyl chloride resin are melt-kneaded with a closed pressure kneader (manufactured by Moriyama Seisakusho), and the resulting kneaded product is extruded from an extrusion molding machine through a molding die. A rod-shaped molded body having a length of 15 cm and a diameter of 3 mm is obtained.
  • Formulation Example 13 Any one of Compounds 1-19 100 mg, lactose 68.75 mg, corn starch 237.5 mg, microcrystalline cellulose 43.75 mg, polyvinylpyrrolidone 18.75 mg, sodium carboxymethyl starch 28.75 mg, and magnesium stearate 5 mg is mixed and the resulting mixture is compressed to an appropriate size to obtain tablets.
  • Formulation Example 14 Any one of Compounds 1 to 19 25 mg, lactose 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose are mixed in an appropriate amount, and the resulting mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule And a capsule is obtained.
  • Formulation Example 15 Any one of Compounds 1-19 100 mg, fumaric acid 500 mg, sodium chloride 2000 mg, methylparaben 150 mg, propylparaben 50 mg, granule sugar 25000 mg, sorbitol (70% solution) 13000 mg, VeegumK (VanderbiltCo.) 100 mg, flavor 35 mg, and coloring Distilled water is added to 500 mg of the preparation so that the final volume becomes 100 mL, and mixed to obtain a suspension for oral administration.
  • VanderbiltCo. VeegumK
  • Formulation Example 16 5% by weight of any one of compounds 1 to 19 is dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol, and 30% by weight of propylene glycol, and the pH of this solution becomes 6.0 to 6.5. Thus, after adding a phosphate buffer solution, water is added as the remainder, and the liquid agent for oral administration is obtained.
  • Formulation Example 17 5% by weight of aluminum distearate in 57% by weight of fractionated coconut oil and 3% by weight of polysorbate 85 is added and dispersed by heating. This is cooled to room temperature and 25% by weight of saccharin is dispersed in the oily vehicle. To this, 10% by weight of any one of compounds 1 to 19 is allocated to obtain a paste preparation for oral administration.
  • Formulation Example 18 5% by weight of any one of compounds 1 to 19 is mixed with 95% by weight of limestone powder, and granules for oral administration are obtained using a wet granulation method.
  • Formulation Example 19 5 parts of any one of compounds 1 to 19 are dissolved in 80 parts of diethylene glycol monoethyl ether, and 15 parts of propylene carbonate are mixed with this to obtain a spot-on solution.
  • Formulation Example 20 10 parts of any one of compounds 1 to 19 are dissolved in 70 parts of diethylene glycol monoethyl ether, and 20 parts of 2-octyldodecanol is mixed with it to obtain a pour-on solution.
  • Formulation Example 22 Any one of compounds 1 to 19 0.15% by weight, animal feed 95% by weight, and 4.85% by weight of a mixture composed of dicalcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk) are sufficiently stirred and mixed. Obtain a premix for animal feed.
  • Formulation Example 23 7.2 g of any one of compounds 1 to 19 and 92.8 g of Fosco (registered trademark) S-55 (manufactured by Maruishi Pharmaceutical Co., Ltd.) are dissolved and mixed at 100 ° C., poured into a suppository, and solidified by cooling. To obtain a suppository.
  • Fosco registered trademark
  • S-55 manufactured by Maruishi Pharmaceutical Co., Ltd.
  • Cb number of insects before treatment in the untreated group
  • Cai number of live parasites when observed in the untreated group
  • Tb number of insects before treatment in the treated group
  • Tai number of live parasitic insects during observation of the treated group
  • the group refers to a group in which a preparation diluted with the same amount of water as the treatment group was sprayed on the preparation not containing the compound of the present invention in Preparation Example 5.
  • the treatment groups of all the compounds tested showed a control value of 90% or more.
  • Test example 2 The preparation of Compound 10 or 17 obtained by Preparation Example 5 was diluted with water so that the concentration of each compound was 200 ppm to obtain a diluted solution.
  • cucumber seedlings planted in plastic cups were irrigated with 5 mL of the diluted solution and kept in a 25 ° C. greenhouse for 7 days. After inoculating about 30 Aphis gossypi (all stages) on the cucumber leaf surface and keeping it in the greenhouse for another 6 days, the number of live aphids on the cucumber leaf was investigated. The control value was calculated by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Cai number of live parasites when observed in the untreated group
  • Tb number of insects before treatment in the treated group
  • Tai number of live parasitic insects during observation of the treated group
  • the group refers to a group in which a preparation diluted with the same amount of water as the treatment group was sprayed on the preparation not containing the compound of the present invention in Preparation Example 5.
  • the treatment groups of all the compounds tested showed a control value of 90% or more.
  • Test example 3 The preparation of Compound 2, 10, 16 or 17 obtained in Formulation Example 5 was diluted with water so that the concentration of each compound was 200 ppm to obtain a diluted solution. 10 mL of the diluted solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the green planthopper (Nilaparvata lugens) were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthopper infested with rice was investigated, and the control value was determined by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Cai number of insects at the time of observation in the untreated group
  • Tb number of insects before the treatment in the treated group
  • Tai number of insects at the time of observation in the treated group
  • this refers to a group in which a preparation containing no compound of the present invention was sprayed with a solution diluted with the same amount of water as the treatment group.
  • the treatment groups of all the compounds tested showed a control value of 90% or more.
  • Test example 4 The formulation of Compound 10 or 16 obtained by Formulation Example 5 was diluted with water so that the concentration of the compound was 250 ppm to obtain a diluted solution. On the other hand, 5 mL of the diluted solution was irrigated to rice seedlings planted in plastic cups (2 weeks after sowing, the second leaf development stage) and kept in a 25 ° C. greenhouse for 7 days. After releasing 20 3-4 instar larvae of the green planthopper (Nilaparvata lugens) and keeping it in the greenhouse for another 6 days, the number of surviving insects parasitic on the rice leaves was investigated, and the control value was calculated by the following formula: Asked.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Cai number of live parasites when observed in the untreated group
  • Tb number of insects before treatment in the treated group
  • Tai number of live parasitic insects during observation of the treated group
  • the group refers to a group in which a preparation diluted with the same amount of water as the treatment group was sprayed on the preparation not containing the compound of the present invention in Preparation Example 5. As a result, the treatment group of all the compounds tested showed a control value of 90% or more.
  • Test Example 5 The preparation of Compound 3 or 12 obtained in Formulation Example 5 was diluted with water so that the concentration of each compound was 200 ppm to obtain a diluted solution.
  • adult whitefly (Bemisia tabaci) was released on tomato seedlings (third true leaf development stage) planted in polyethylene cups, and eggs were laid for about 72 hours.
  • the tomato seedlings were kept in the greenhouse for 8 days, and the diluted solution was sprayed at a rate of 20 mL / cup to the place where the larvae hatched from the delivered eggs, and kept in the greenhouse at 25 ° C. Seven days later, the number of surviving larvae on the tomato leaves was examined, and the control value was determined by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • the treatment groups of all the compounds tested showed a control value of 90% or more.
  • Test Example 7 The preparation of Compound 12 or 13 obtained in Formulation Example 5 was diluted with water so that the concentration of each compound was 500 ppm to obtain a diluted solution.
  • a filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, and 0.7 mL of the diluted solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food.
  • Test Example 8 The formulation of Compound 12 obtained in Formulation Example 5 was diluted with water so that the concentration of the compound was 500 ppm to obtain a diluted solution.
  • a filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, and 0.7 mL of the diluted solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food.
  • the compound of the present invention has a controlling effect on harmful arthropods and is useful as an active ingredient of a harmful arthropod controlling agent.

Abstract

L'invention concerne un composé représenté par la formule (I), ou un N-oxyde de celui-ci qui possède un excellent effet pour lutter contre les arthropodes nuisibles. ［Dans la formule, A représente un atome d'azote ou ＣＲ6; ＲA ou ＲB représente －ＯＳＯ2ＣＦ3, et l'autre un atome d'hydrogène; Ｒ1 représente un groupe alkyle en C1-C4, un groupe cyclopropyle ou un groupe cyclopropylméthyle; Ｒ2 représente un atome d'hydrogène, ou similaire; Ｒ3 et Ｒ4 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène; Ｒ5 représente un atome d'hydrogène, ou similaire; et n représente 0, 1 ou 2. ］
PCT/JP2016/052090 2015-02-03 2016-01-26 Composé benzimidazole, et application de celui-ci pour lutter contre les arthropodes nuisibles WO2016125621A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015019056 2015-02-03
JP2015-019056 2015-02-03

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Publication Number Publication Date
WO2016125621A1 true WO2016125621A1 (fr) 2016-08-11

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WO2018065292A1 (fr) 2016-10-06 2018-04-12 Bayer Cropscience Aktiengesellschaft Dérivés d'hétérocyclène bicycliques condensés substitués par 2 (het)-aryle utilisés comme pesticides pour lutter contre les bioagresseurs
WO2018065288A1 (fr) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft Dérivés de 2-[2-phényl-1-(sulfonylméthyl)vinyl]-imidazo[4,5-b]pyridine et composés apparentés utilisés comme pesticides en protection des plantes
WO2018130443A1 (fr) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Dérivés hétérocycliques utilisés comme pesticides
WO2018130437A1 (fr) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Dérivés hétérocycliques utilisés comme pesticides
WO2018139436A1 (fr) 2017-01-24 2018-08-02 住友化学株式会社 Composé hétérocyclique fusionné et composition le contenant
WO2018141954A1 (fr) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Dérivés d'imidazopyridine substitués par un aryle ou hétéroaryle et leur utilisation comme pesticides
WO2018141955A1 (fr) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Procédé de production de dérivés d'imidazopyridines halogénés
WO2019065568A1 (fr) * 2017-09-26 2019-04-04 住友化学株式会社 Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles contenant celui-ci
WO2021033141A1 (fr) 2019-08-20 2021-02-25 Pi Industries Ltd. Composés hétérocycliques fusionnés et leur utilisation en tant qu'agents de lutte contre les organismes nuisibles
WO2022002818A1 (fr) 2020-07-02 2022-01-06 Bayer Aktiengesellschaft Dérivés d'hétérocyclène utiles en tant qu'agents de lutte contre les nuisibles
US11926623B2 (en) 2018-06-26 2024-03-12 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides

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WO1994005633A1 (fr) * 1992-09-01 1994-03-17 Ciba-Geigy Ag 3-cyano-4-halogeno-2-(subst phenyl)-pyrroles utilises comme pesticides et fongicides
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WO2013163244A1 (fr) * 2012-04-26 2013-10-31 Bristol-Myers Squibb Company Dérivés d'imidazothiadiazole utilisés en tant qu'inhibiteurs des récepteurs activés par la protéase 4 (par4) pour traiter l'agrégation plaquettaire
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WO2014037349A1 (fr) * 2012-09-05 2014-03-13 Bayer Cropscience Ag Utilisation d'acide 2,3-dihydro-1-benzofurane-4-carboxylique substitué ou de ses sels comme principes actifs contre le stress abiotique des plantes
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018065292A1 (fr) 2016-10-06 2018-04-12 Bayer Cropscience Aktiengesellschaft Dérivés d'hétérocyclène bicycliques condensés substitués par 2 (het)-aryle utilisés comme pesticides pour lutter contre les bioagresseurs
US11339155B2 (en) 2016-10-06 2022-05-24 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
WO2018065288A1 (fr) 2016-10-07 2018-04-12 Bayer Cropscience Aktiengesellschaft Dérivés de 2-[2-phényl-1-(sulfonylméthyl)vinyl]-imidazo[4,5-b]pyridine et composés apparentés utilisés comme pesticides en protection des plantes
US11058115B2 (en) 2017-01-10 2021-07-13 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2018130443A1 (fr) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Dérivés hétérocycliques utilisés comme pesticides
WO2018130437A1 (fr) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Dérivés hétérocycliques utilisés comme pesticides
US11083199B2 (en) 2017-01-10 2021-08-10 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2018139436A1 (fr) 2017-01-24 2018-08-02 住友化学株式会社 Composé hétérocyclique fusionné et composition le contenant
US10772332B2 (en) 2017-02-06 2020-09-15 Bayer Aktiengesellschaft 2-(het)aryl-substituted fused heterocycle derivatives as pesticides
US11072609B2 (en) 2017-02-06 2021-07-27 Bayer Aktiengesellschaft Method for preparing halogenated imidazopyridine derivatives
WO2018141955A1 (fr) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Procédé de production de dérivés d'imidazopyridines halogénés
WO2018141954A1 (fr) 2017-02-06 2018-08-09 Bayer Aktiengesellschaft Dérivés d'imidazopyridine substitués par un aryle ou hétéroaryle et leur utilisation comme pesticides
WO2019065568A1 (fr) * 2017-09-26 2019-04-04 住友化学株式会社 Composé hétérocyclique et agent de lutte contre les arthropodes nuisibles contenant celui-ci
US11926623B2 (en) 2018-06-26 2024-03-12 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
WO2021033141A1 (fr) 2019-08-20 2021-02-25 Pi Industries Ltd. Composés hétérocycliques fusionnés et leur utilisation en tant qu'agents de lutte contre les organismes nuisibles
WO2022002818A1 (fr) 2020-07-02 2022-01-06 Bayer Aktiengesellschaft Dérivés d'hétérocyclène utiles en tant qu'agents de lutte contre les nuisibles

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