WO2016125622A1 - Composé benzoxazole, et application de celui-ci pour lutter contre les arthropodes nuisibles - Google Patents

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

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Publication number
WO2016125622A1
WO2016125622A1 PCT/JP2016/052091 JP2016052091W WO2016125622A1 WO 2016125622 A1 WO2016125622 A1 WO 2016125622A1 JP 2016052091 W JP2016052091 W JP 2016052091W WO 2016125622 A1 WO2016125622 A1 WO 2016125622A1
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group
compound
hydrogen atom
atom
halogen atoms
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PCT/JP2016/052091
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Japanese (ja)
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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
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a benzoxazole 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 benzoxazole compound represented by the following formula (I) has an excellent control effect against harmful arthropods, leading to the present invention. .
  • A represents a nitrogen atom or CR 5
  • One of 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 and R 3 each independently represent a hydrogen atom or a halogen atom
  • R 4 and R 5 each independently represents a hydrogen atom
  • —S (O) m R 6 ⁇ 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 7 , —OR 7 , —NR 8 R 9 , —C (O) R 10 , —COOR 10 , —C (O) NR 8 R 9 , a phenyl group, a 5- to 6-membered heteroaryl group (provided that the phenyl group and the 5- to 6-membered heteroaryl group may have one or more atoms or substituents selected from group X; When it has two or more atoms or substituents, these atoms and substituents may be the same or different.
  • R 10 and R 12 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 4 and R 5 each independently represents one or more selected from a hydrogen atom, —R 6 , —S (O) m R 6 , —OR 6 , —NR 8 R 9 , —COOR 6 , group X
  • the benzoxazole compound according to [1], wherein S (O) p R 6 R 11 .
  • R A is —OSO 2 CF 3 and R B is a hydrogen atom.
  • R 1 is an ethyl group
  • R 2 and R 3 are both hydrogen atoms
  • R 4 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 5 is a hydrogen atom or a halogen atom.
  • a harmful arthropod control agent comprising the benzoxazole 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 benzoxazole 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.
  • a compound according to Aspect 3 wherein R 4 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 4 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
  • a compound that is an aryl group A compound that is an aryl group.
  • a compound according to Aspect 6 wherein R 4 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • R 4 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • Formula (Ib) [Wherein the symbols have the same meaning as described above. ] The compound shown.
  • R 1 is a C1-C4 alkyl group
  • R 4 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
  • a compound that is an aryl group
  • R 4 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 4 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
  • group X A compound that is an aryl group.
  • R 4 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having 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 And R 3 is a hydrogen atom
  • R 4 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 1,2,4-triazolyl group.
  • R 4 is a hydrogen atom.
  • 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 And R 3 is a hydrogen atom
  • R 4 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 1,2,4-triazolyl group.
  • R 4 is a hydrogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 1,2,4-triazolyl group in Aspect 16-1.
  • R A is —OSO 2 CF 3
  • R B is a hydrogen atom
  • A is CH
  • R 1 is a C1-C4 alkyl group
  • R 4 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or a 1,2,4-triazolyl group.
  • R 4 is a hydrogen atom, a halogen atom, or a C1-C6 alkyl group optionally having one or more halogen atoms.
  • Aspect 18 A compound according to Aspect 2, wherein R 4 is a hydrogen atom.
  • Aspect 19 A compound according to Aspect 2, wherein R 4 is a halogen atom.
  • Aspect 20 A compound according to Aspect 2, wherein R 4 is a C1-C6 alkyl group optionally having one or more halogen atoms.
  • Aspect 21 The compound according to Aspect 9, wherein R 4 is a hydrogen atom.
  • Aspect 22 The compound according to Aspect 9, wherein R 4 is a 1,2,4-triazolyl group.
  • R 1 is a C1-C4 alkyl group
  • R 4 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 1 is an ethyl group and R 4 is a hydrogen atom, a halogen atom, a C1-C6 alkyl group optionally having one or more halogen atoms, or 1,2,4- A compound that is a triazolyl group.
  • the compound of the present invention and the intermediate compound can be produced, for example, according to the methods described in the following production methods 1 to 5 and reference production methods 1 to 4.
  • a compound represented by the formula (Inn1) (hereinafter referred to as the compound (Inn1)) is a compound represented by the formula (Inn0) (hereinafter referred to as the compound (Inn0)). It can be produced by oxidizing. [Wherein the symbols have the same meaning as described above. ]
  • 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.
  • a base is usually used in an amount of 0.01 to 1 mol with respect to 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 referred to as the compound (In2)) is the compound represented by the formula (In3) (hereinafter referred to as the compound (In3)). It can be produced by oxidizing. [Wherein, r represents 0 or 1 and other symbols have the same meaning as described above. ] In this reaction, 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 In this case, 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 can be produced by dehydrating a compound represented by the formula (M1) (hereinafter referred to as compound (M1)). [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 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).
  • aromatic hydrocarbons such as toluene, benzene, and xylene (hereinafter referred to as aromatic hydrocarbons), esters, nitriles, and mixtures thereof.
  • a condensing agent or an acid can be used.
  • the condensing agent used in the reaction include organic bases such as triphenylphosphine, triethylamine and pyridine (hereinafter referred to as organic bases) and a mixture of carbon tetrachloride, azodiesters such as triphenylphosphine and diethyl azodicarboxylate. A mixture of the like.
  • Examples of the acid used for the reaction include sulfonic acids such as paratoluenesulfonic acid.
  • the condensing agent when a condensing agent is used, the condensing agent is usually in a proportion of 1 to 5 mol, and when an acid is used, the acid is usually in a proportion of 0.1 to 5 mol.
  • 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.
  • a compound represented by formula (M23) (hereinafter referred to as compound (M23)) is a compound represented by formula (M2) (hereinafter referred to as compound (M2)) and a compound represented by formula (M3) ( Hereinafter, it can be produced by reacting with compound (M3).
  • the reaction is usually performed in the presence of a solvent. Examples of the solvent used for the reaction include aromatic hydrocarbons.
  • compound (M3) is usually used at a ratio of 1 to 1.2 mol with respect to 1 mol of compound (M2).
  • the reaction temperature of the reaction is usually in the range of 50 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M3) can be produced according to the method described in International Publication No. 2012/0886848 or International Publication No. 2013/018928.
  • the compound of the present invention can be produced by reacting the compound (M23) with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used for the reaction include aromatic hydrocarbons.
  • An example of the oxidizing agent used in the reaction is iodine.
  • the reaction temperature of the reaction is usually in the range of 50 to 150 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be produced in one pot from the compound (M2) without isolating the compound (23).
  • the compound of the present invention is produced by reacting a compound represented by the formula (M4) (hereinafter referred to as compound (M4)) with trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride in the presence of a base.
  • M4 a compound represented by the formula (M4)
  • M4 trifluoromethanesulfonic anhydride or trifluoromethanesulfonyl chloride
  • Examples of the solvent used in the reaction include aliphatic hydrocarbons such as ethers, hexane and heptane (hereinafter referred to as aliphatic hydrocarbons), aromatic hydrocarbons, halogenated hydrocarbons, esters, and nitriles. , Aprotic polar solvents and mixtures thereof.
  • Examples of the base used for the reaction include organic bases.
  • the reaction is carried out at a ratio of usually 0.8 to 1.5 mol of trifluoromethanesulfonic anhydride or trifluoromethanesulfonic acid chloride and usually 0.8 to 1.5 mol of base with respect to 1 mol of compound (M4). It is used in the ratio.
  • 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 (M1) can be produced by reacting compound (M2) with a compound represented by formula (M5) (hereinafter referred to as compound (M5)).
  • compound (M5) a compound represented by formula (M5)
  • X represents a hydroxyl group or a chlorine atom, and other symbols have the same meaning as described above.
  • This reaction can be carried out according to the method described in International Publication No. 2013/018928.
  • Compound (M5) can be produced according to the method described in International Publication No. 2012/088684 or International Publication No. 2013/018928.
  • Reference production method 2 Compound (M2) can be produced by the method shown below. [Wherein the symbols have the same meaning as described above. ]
  • the step of producing a compound represented by formula (M7) (hereinafter referred to as compound (M7)) from a compound represented by formula (M6) can be carried out according to the method described in Production Method 5.
  • the base is preferably added after completion of the reaction.
  • the step of producing a compound represented by formula (M8) by nitrating compound (M7) (hereinafter referred to as compound (M8)) should be carried out according to the method described in International Publication No. 2013/018928. Can do.
  • the step of producing compound (M2) by reducing compound (M8) is a method of using metallic iron described in New Experimental Chemistry Course 15 Oxidation and Reduction [II] (Maruzen) as a reducing reagent, or a method analogous thereto Can be implemented.
  • Compound (M4) can be produced by reacting a compound represented by formula (M9) (hereinafter referred to as compound (M9)) with iodotrimethylsilane.
  • compound (M9) a compound represented by formula (M9)
  • one of R F and R G represents a methoxy group, the other represents a hydrogen atom, and the other symbols represent the same meaning as described above.
  • the reaction is usually performed in the presence of a solvent. Nitriles are mentioned as a solvent used for reaction. Instead of iodotrimethylsilane used in the reaction, a mixture of chlorotrimethylsilane and sodium iodide can also be used.
  • the reaction is carried out at a ratio of usually 1 to 10 moles of iodotrimethylsilane, usually 1 to 10 moles of chlorotrimethylsilane, and usually 1 to 10 moles of sodium iodide with respect to 1 mole of compound (M9). Used.
  • 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 1 to 48 hours.
  • Reference production method 4 Compound (M9) can be produced by the method shown below. [Wherein the symbols have the same meaning as described above. ]
  • the step of producing a compound represented by the formula (M11) by reacting the compound represented by the formula (M10) with the compound (M5) (hereinafter referred to as the compound (M11)) is the method described in Reference Production Method 1. It can implement according to.
  • the step of producing compound (M9) by reacting compound (M11) with a condensing agent or acid can be carried out according to the method described in Production Method 3.
  • the compound represented by the formula (M10) is a known product or can be produced by a known method.
  • 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 (M1), compound (M7), compound (M8) , Compound (M2), Compound (M4), Compound (M11) or Compound (M9) can be isolated.
  • the isolated compound of the present invention, compound (M1), compound (M7), compound (M8), compound (M2), compound (M4), compound (M11) or compound (M9) is recrystallized, chromatographed, etc. Can be further purified by
  • Me means a methyl group
  • Tr means a 1,2,4-triazol-1-yl group
  • Pz means a pyrazol-1-yl group.
  • [A; R 4 ; 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 4 ; 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
  • chemical shift ( ⁇ ) was expressed in ppm.
  • Production Example 4 (1) A mixture of 500 mg of 3-ethylsulfanylpyridine-2-carboxylic acid, 0.5 mL of thionyl chloride, 1 drop of DMF and 5 mL of toluene was stirred at 100 ° C. for 2 hours and concentrated under reduced pressure. A mixture of the obtained residue and 6 mL of THF was added to a mixture of 380 mg of 2-amino-4-methoxyphenol and 6 mL of THF under ice-cooling, and the mixture was brought to room temperature and stirred at room temperature for 1 hour. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
  • a part represents a weight part.
  • Formulation Example 1 10 parts of any one of compounds 1 to 12 are dissolved in a mixture of 35 parts of xylene and 35 parts of DMF, and 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 12 are added and mixed to each water. Get a glaze.
  • Formulation Example 4 1 part of any one of compounds 1 to 12 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 to the resulting mixture and stirred sufficiently. 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 12, and 55 parts of water are mixed and finely divided by a wet grinding method. Each flowable agent is obtained by grinding.
  • Formulation Example 6 0.1 part of any one of compounds 1 to 12 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 12 is dissolved in 0.5 mL of acetone, and this solution is added dropwise to 5 g of animal solid feed powder (bred breeding solid feed powder CE-2, Nippon Claire Co., Ltd.). Mix evenly. Then acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder termed breeding solid feed powder CE-2, Nippon Claire Co., Ltd.
  • Formulation Example 8 0.1 part of any one of compounds 1 to 12 and 49.9 parts of neothiozole (manufactured by 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 12, 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
  • xylene 3.39 parts of kerosene
  • 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.
  • LPG propellant
  • Formulation Example 10 0.1 g of any one of compounds 1 to 12 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 12 and 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACRIFT (registered trademark) WD301, manufactured by Sumitomo Chemical Co., Ltd.)
  • 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 12 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 1-12 100 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 12 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 1-12 100 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 12 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 12 is allocated to obtain a paste preparation for oral administration.
  • Formulation Example 18 5% by weight of any one of compounds 1 to 12 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 12 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 12 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 12 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 12 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.
  • Test example 1 The preparation of Compound 1, 3, 4, 5, 7, 9, 10 or 12 obtained in Formulation Example 5 was diluted with water so that the concentration of each compound was 500 ppm to obtain a diluted solution.
  • about 30 Aphis gossypi all stages were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups, and left for 1 day. Scattered.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • 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. As a result, the control value of 90% or more was exhibited in all the treatment sections where the compounds of the present invention were tested.
  • Test example 2 The preparation of Compound 4 or 5 obtained in Preparation Example 5 was diluted with water so that the concentration of each compound was 500 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 control value of 90% or more was exhibited in all the treatment sections where the compounds of the present invention were tested.
  • Test example 3 The formulation of Compound 4 obtained in Formulation Example 5 was diluted with water so that the concentration of Compound 4 was 200 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 section in which Compound 4 was tested showed a control value of 100%.
  • Test example 4 The preparation of Compound 1, 3, 4, 5, 7, 9, 10 or 12 obtained in Formulation Example 5 was diluted with water so that the concentration of each compound was 500 ppm to obtain a diluted solution.
  • Test Example 5 The formulation of Compound 4 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.
  • Test Example 6 The preparation of Compound 3 or 9 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.
  • 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 benzoxazole représenté par la formule (I) qui possède un excellent effet pour lutter contre les arthropodes nuisibles. ［Dans la formule, A représente un atome d'azote ou un ＣＲ5 ; 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 et Ｒ3 représentent chacun indépendamment un atome d'hydrogène ou un atome d'halogène ; Ｒ4 et Ｒ5 représentent chacun indépendamment un atome d'hydrogène, －Ｓ（Ｏ）mＲ6 ｛m représente 0, 1 ou 2. ｝, un groupe cycloalkyle en C3-C6 pouvant posséder un atome d'halogène ou plus, ou similaire ; et n représente 0, 1 ou 2. ］
PCT/JP2016/052091 2015-02-03 2016-01-26 Composé benzoxazole, et application de celui-ci pour lutter contre les arthropodes nuisibles WO2016125622A1 (fr)

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Cited By (8)

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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
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
WO2020054790A1 (fr) * 2018-09-13 2020-03-19 住友化学株式会社 Composé de bipyridine et son utilisation
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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US11339155B2 (en) 2016-10-06 2022-05-24 Bayer Cropscience Aktiengesellschaft 2-(het)aryl-substituted fused bicyclic heterocycle derivatives as pesticides
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
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WO2018130437A1 (fr) 2017-01-10 2018-07-19 Bayer Aktiengesellschaft Dérivés hétérocycliques utilisés comme pesticides
US11058115B2 (en) 2017-01-10 2021-07-13 Bayer Aktiengesellschaft Heterocycle derivatives as pesticides
US11083199B2 (en) 2017-01-10 2021-08-10 Bayer Aktiengesellschaft Heterocycle derivatives as 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
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JP7368368B2 (ja) 2018-09-13 2023-10-24 住友化学株式会社 ビピリジン化合物及びその用途
TWI827660B (zh) * 2018-09-13 2024-01-01 日商住友化學股份有限公司 聯吡啶化合物及其用途
WO2020054790A1 (fr) * 2018-09-13 2020-03-19 住友化学株式会社 Composé de bipyridine et son utilisation
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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