WO2016143650A1 - Composé 3-aminooxalylaminobenzamide et son utilisation pour lutter contre des arthropodes nuisibles - Google Patents

Composé 3-aminooxalylaminobenzamide et son utilisation pour lutter contre des arthropodes nuisibles Download PDF

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WO2016143650A1
WO2016143650A1 PCT/JP2016/056540 JP2016056540W WO2016143650A1 WO 2016143650 A1 WO2016143650 A1 WO 2016143650A1 JP 2016056540 W JP2016056540 W JP 2016056540W WO 2016143650 A1 WO2016143650 A1 WO 2016143650A1
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group
compound
haloalkyl
present
alkyl
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政樹 ▲高▼橋
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/12—1,4-Thiazines; Hydrogenated 1,4-thiazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/06—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms

Definitions

  • the present invention relates to certain 3-aminooxalylaminobenzamide compounds and their use for harmful arthropods.
  • Patent Document 1 International Publication No. 2012/164698
  • An object of the present invention is to provide a compound having an excellent controlling effect on harmful arthropods and a method for controlling harmful arthropods using the compound.
  • G 1 and G 5 each independently represent —CR 6 R 7 — or —C (O) —
  • G 2 , G 3 and G 4 each independently represent —CR 6 R 7 — or a single bond
  • Q represents an oxygen atom
  • R 1 and R 3 are each independently a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a —S (O) p- (C1-C6 alkyl) group, a C1-C6 haloalkyl group, a C1-C6 A haloalkoxy group, a —S (O) p — (C1-C6 haloalkyl) group, a halogen atom, a nitro group or a cyano group;
  • R 2 represents a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group or
  • R 8 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a cyano group
  • R 9 represents a C1-C6 alkyl group or a C1-C6 haloalkyl group
  • Each X a independently represents a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, a halogen atom or a cyano group
  • Each Xb independently represents a C1-C6 alkyl group, a C1-C6 alkoxy group, a C1-C6 haloalkyl group, a C1-C6 haloalk
  • R 1 and R 3 are each independently a hydrogen atom, a C1-C6 alkyl group, a C1-C6 alkoxy group, a —S (O) p — (C1-C6 alkyl) group, a C1-C6 haloalkyl group, A C1-C6 haloalkoxy group, —S (O) p — (C1-C6 haloalkyl) group or a halogen atom
  • R 4 and R 5 are each independently a hydrogen atom, a C1-C6 alkyl group, a (C1-C6 alkyl) carbonyl group, a C1-C6 haloalkyl group or a (C1-C6 haloalkyl) carbonyl group
  • R 6 and R 7 are each independently a hydrogen atom, a
  • G 1 and G 5 are each independently —CR 6 R 7 —
  • R 1 and R 3 are each independently a hydrogen atom, a C1-C3 alkyl group, a C1-C3 alkoxy group, a —S (O) p — (C1-C3 alkyl) group, a C1-C3 haloalkyl group, a C1-C3 A haloalkoxy group, a —S (O) p — (C1-C3 haloalkyl) group or a halogen atom
  • R 4 and R 5 are each independently a hydrogen atom or a C1-C3 alkyl group
  • R 6 and R 7 are each independently a hydrogen atom, a C1-C3 alkyl group or a C1-C3 haloalkyl group
  • R 8 is a hydrogen atom, a methyl group, an ethyl group or a cyano group
  • R 9 is a methyl
  • [6] The compound according to any one of [1] to [5], wherein R 2 is a C1-C6 haloalkyl group.
  • R 2 is a C1-C6 haloalkoxy group.
  • R 2 is a —S (O) p — (C1-C6 haloalkyl) group.
  • a harmful arthropod control composition comprising the compound according to any one of [1] to [8] and an inert carrier.
  • a method for controlling harmful arthropods which comprises applying an effective amount of the compound according to any one of [1] to [8] to harmful arthropods or harmful arthropod habitats.
  • the compound of the present invention Since the compound of the present invention has an excellent control activity against harmful arthropods, it is useful as an active ingredient of a harmful arthropod control agent.
  • C1-C6 alkyl group includes, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group and tert-butyl group.
  • the “C1-C6 alkyl group” includes a “C1-C4 alkyl group” and further a “C1-C3 alkyl group”.
  • examples of the “C1-C6 alkoxy group” include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group.
  • the “C1-C6 alkoxy group” includes a “C1-C4 alkoxy group” and further a “C1-C3 alkoxy group”.
  • the “—S (O) p — (C1-C6 alkyl) group” is a group in which the “C1-C6 alkyl group” is bonded to the sulfur atom of S (O) p , for example, a methylsulfanyl group.
  • the “C1-C6 haloalkyl group” is a group in which one or more hydrogen atoms of the “C1-C6 alkyl group” are substituted with a halogen atom, such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group.
  • the “C1-C6 haloalkoxy group” is a group in which one or more hydrogen atoms of the “C1-C6 alkoxy group” are substituted with a halogen atom, such as a fluoromethoxy group, a difluoromethoxy group, a trifluoro group.
  • Methoxy group chlorodifluoromethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, heptafluoropropoxy group, heptafluoroisopropoxy group, 1,1,2,2,3,3-hexafluoropropoxy group And the groups 2,2,2-trifluoro-1- (trifluoromethyl) ethoxy and trichloromethoxy.
  • the “—S (O) p — (C1-C6 haloalkyl) group” is a group in which the “C1-C6 haloalkyl group” is bonded to the sulfur atom of S (O) p.
  • Methyl) sulfanyl group (trifluoromethane) sulfinyl group, (trifluoromethane) sulfonyl group, (pentafluoroethyl) sulfanyl group, (pentafluoroethane) sulfinyl group, (pentafluoroethane) sulfonyl group, (heptafluoroisopropyl) sulfanyl group , (Heptafluoroisopropane) sulfinyl group and (heptafluoroisopropane) sulfonyl group.
  • halogen atom represents a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • the compound of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and there may be two or more optical isomers. All of the optical isomers and a mixture containing them in an arbitrary ratio are also contained.
  • the compound of the present invention may contain two or more geometric isomers derived from a carbon-carbon double bond, sulfur-nitrogen double bond, or cyclic structure in the structure. It also contains all geometric isomers and mixtures containing them in any proportion.
  • Examples of the compound of the present invention include the following compounds.
  • a compound wherein G 1 is —CR 6 R 7 —;
  • G 1 is —CR 6 R 7 —, and R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group;
  • a compound wherein G 1 is —CH 2 —;
  • a compound wherein G 1 is —CH (CH 3 ) —;
  • a compound wherein G 2 is —CR 6 R 7 —;
  • G 2 is —CR 6 R 7 —, and R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group;
  • a compound wherein G 2 is —CH 2 —;
  • a compound wherein G 2 is —CH (CH 3 ) —;
  • a compound in which G 2 is a single bond;
  • a compound wherein G 3 is —CR 6 R 7 —;
  • G 3 is —CR 6 R 7 —, and R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group;
  • a compound wherein G 3 is —CH 2 —;
  • a compound wherein G 3 is —CH (CH 3 ) —;
  • a compound in which G 3 is a single bond;
  • a compound wherein G 4 is —CR 6 R 7 —;
  • G 4 is —CR 6 R 7 —, and R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group;
  • a compound wherein G 4 is —CH 2 —;
  • a compound wherein G 4 is —CH (CH 3 ) —;
  • a compound in which G 4 is a single bond;
  • G 1 and G 5 each independently represent —CHR 6 —
  • G 2 , G 3 and G 4 each independently represent —CHR 6 — or a single bond, and at least one of G 2 , G 3 and G 4 is —CHR 6 —
  • G 1 , G 2 and G 5 are —CHR 6 —
  • G 3 and G 4 are each independently —CHR 6 — or a single bond
  • R 6 is independently a hydrogen atom or a C1-C6 alkyl group
  • a compound wherein G 5 is —CR 6 R 7 —;
  • G 5 is —CR 6 R 7 —, and R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group, or a C1-C6 haloalkyl group;
  • a compound wherein G 5 is —CH 2 —;
  • a compound wherein G 5 is —CH (CH 3 ) —;
  • a compound in which Q is an oxygen atom;
  • Q is NR 8 and R 8 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group or a cyano group;
  • Q is NR 8 and R 8 is a hydrogen atom, a C1-C6 alkyl group, or a cyano group;
  • a compound wherein Q is NH;
  • a compound wherein Q is NCN;
  • Q is NC (O) R 9 and R 9 is a C1-C6 alkyl group or a C1-C6 haloalkyl group;
  • a compound in which Q is NC (O) CH 3 or NC (O) CF 3 ;
  • a compound in which Q is unsubstituted
  • a compound wherein R 1 is a hydrogen atom; In the compounds of the present invention, a compound wherein R 1 is a C1-C6 alkyl group; In the compounds of the present invention, a compound wherein R 1 is a C1-C6 haloalkyl group; In the compound of the present invention, R 1 is a C1-C6 haloalkoxy group, —S— (C1-C6 haloalkyl) group, —S (O) — (C1-C6 haloalkyl) group, or —S (O) 2 — ( A compound which is a C1-C6 haloalkyl) group; In the compounds of the present invention, a compound wherein R 1 is a halogen atom; In the compounds of the present invention, a compound wherein R 1 is a methyl group, an ethyl group, a propyl group, or an isopropyl group; In the compounds of the present invention,
  • a compound wherein R 2 is a C1-C6 haloalkyl group; In the compounds of the present invention, a compound wherein R 2 is a C1-C6 haloalkoxy group; In the compounds of the present invention, a compound wherein R 2 is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group; In the compound of the present invention, a compound wherein R 2 is a trifluoromethoxy group, a pentafluoroethoxy group, a heptafluoropropoxy group, or a heptafluoroisopropoxy group;
  • a compound wherein R 3 is a hydrogen atom; In the compounds of the present invention, a compound wherein R 3 is a C1-C6 alkyl group; In the compounds of the present invention, a compound wherein R 3 is a C1-C6 haloalkyl group; In the compounds of the present invention, a compound wherein R 3 is a C1-C6 haloalkoxy group; In the compounds of the present invention, a compound wherein R 3 is a —S— (C1-C6 haloalkyl) group; In the compounds of the present invention, a compound wherein R 3 is a —S (O) — (C1-C6 haloalkyl) group; In the compounds of the present invention, a compound wherein R 3 is a —S (O) 2 — (C1-C6 haloalkyl) group; In the compounds of the present invention, a compound wherein R 3 is a halogen atom;
  • either one of R 1 and R 3 is a halogen atom or a C1-C6 alkyl group, and the other is a C1-C6 alkyl group, a C1-C6 alkoxy group, —S (O) p —
  • R 1 or R 3 is a bromine atom, an iodine atom or a C1-C3 alkyl group, and the other is a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C1-C3 haloalkoxy group.
  • X a is each independently a C1-C6 alkyl group or a C1-C6 haloalkyl group, and m is an integer of 0-4;
  • compounds wherein X a is each independently a C1-C6 alkoxy group or a C1-C6 haloalkoxy group, and m is an integer of 0-4;
  • X a is independently a halogen atom, and m is an integer of 0 to 4;
  • G 1 , G 2 and G 5 are —CR 6 R 7 —, G 3 and G 4 are each independently —CR 6 R 7 — or a single bond, Q is absent or is an oxygen atom, NR 8 , or NC (O) R 9 ;
  • R 6 and R 7 are each independently a hydrogen atom, a C1-C6 alkyl group or a C1-C6 haloalkyl group,
  • R 1 is a hydrogen atom, a C1-C6 alkyl group or a halogen atom
  • R 3 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or a —S (O) p — (C1-C6 haloalkyl) group
  • R 4 and R 5 are each independently a hydrogen atom, a C1-C6 alkyl group or a (C1-C6 alkyl) carbon
  • G 1 , G 2 and G 5 are —CHR 6 —, G 3 and G 4 are each independently —CHR 6 — or a single bond, Q is absent or is an oxygen atom, NR 8 , or NC (O) R 9 ;
  • Each R 6 is independently a hydrogen atom or a C1-C6 alkyl group;
  • R 1 is a hydrogen atom, a C1-C6 alkyl group or a halogen atom,
  • R 2 is a C1-C6 haloalkyl group or a C1-C6 haloalkoxy group,
  • R 3 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group, or a C1-C6 haloalkylsulfanyl group
  • R 4 and R 5 are each independently a hydrogen atom or a C1-C6 alkyl group
  • R 8 is
  • the compound of the present invention and the intermediate compound can be produced, for example, according to the following production methods 1 to 10.
  • Manufacturing method 1 The compound of the present invention can be produced according to the following method.
  • Compound (M2) can be produced by reacting compound (M1) with a compound represented by formula (R1) (hereinafter referred to as compound (R1)) in the presence of a base.
  • Compound (M1) can be produced according to the method described in International Publication No. 2005/073165.
  • Compound (R1) is a commercially available compound.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons such as dichloromethane and chloroform (hereinafter referred to as aliphatic halogenated hydrocarbons); nitriles such as acetonitrile (hereinafter referred to as nitriles).
  • Ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether, methyl tert-butyl ether (hereinafter referred to as MTBE), 1,4-dioxane (hereinafter referred to as ethers); acetone, ethyl Ketones such as methyl ketone and isobutyl methyl ketone (hereinafter referred to as ketones); esters such as methyl acetate and ethyl acetate (hereinafter referred to as esters); aromatic hydrocarbons such as toluene and xylene ( Hereinafter referred to as aromatic hydrocarbons); dimethylformamide (hereinafter referred to as DMF) Be), N- methylpyrrolidone, aprotic polar solvents such as dimethyl sulfoxide (hereinafter, referred to as aprotic polar solvent);.. And mixtures thereof.
  • THF tetrahydro
  • Examples of the base used in the reaction include organic bases such as triethylamine, diisopropylethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene (hereinafter referred to as organic bases); Alkali metal carbonates such as sodium and potassium carbonate (hereinafter referred to as alkali metal carbonates); alkaline earth metal carbonates such as calcium carbonate (hereinafter referred to as alkaline earth metal carbonates); sodium hydrogen carbonate and the like Alkali metal hydrogen carbonates (hereinafter referred to as alkali metal hydrogen carbonates); alkali metal hydroxides such as sodium hydroxide and potassium hydroxide (hereinafter referred to as alkali metal hydroxides); Alkaline earth metal hydroxides such as calcium (hereinafter referred to as alkaline earth metal hydroxides); sodium metho Metal alkoxides such as Sid and sodium ethoxide (hereinafter, referred to as metal alkoxides.); Alkali
  • the reaction can be performed by adding a catalyst as necessary.
  • the catalyst used in the reaction include dimethylaminopyridine.
  • the ratio of the compound (R1) is usually 1 to 2 moles
  • the base is usually 1 to 2 moles
  • the catalyst is usually 0.01 to 0.5 moles Used in
  • the reaction temperature is usually in the range of ⁇ 30 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • compound (M2) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound of the present invention can be produced by reacting the compound (M2) with a compound represented by the formula (R2) (hereinafter referred to as compound (R2)).
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, alcohols such as methanol, ethanol, and isopropanol. (Hereinafter referred to as alcohols), water and mixtures thereof.
  • the reaction can be performed by adding a base as necessary.
  • the base used in the reaction include organic bases, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen carbonates, alkali metal hydroxides, alkaline earth metal hydroxides, metal alkoxides. And alkali metal hydrides.
  • the compound (R2) is usually used in a proportion of 1 to 10 mol and the base is usually used in a proportion of 1 to 10 mol with respect to 1 mol of the compound (M2).
  • the reaction temperature is usually in the range of ⁇ 30 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound of the present invention can be obtained by post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer.
  • Manufacturing method 2 The compound of the present invention can also be produced according to the following method.
  • Compound (M3) can be produced by reacting compound (M2) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include water and a mixture of alcohols and water.
  • Examples of the base used in the reaction include alkali metal hydroxides and alkaline earth metal hydroxides.
  • the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M2).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • compound (M3) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • the compound of the present invention can be produced by reacting the compound (M3) and the compound (R2) in the presence of a condensing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, nitrogen-containing aromatics such as pyridine and quinoline. Examples thereof include compounds (hereinafter referred to as nitrogen-containing aromatic compounds), water, and mixtures thereof.
  • the condensing agent examples include carbodiimides such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride and 1,3-dicyclohexylcarbodiimide (hereinafter referred to as carbodiimides), N, N′-carbonyldi- Imidazoles such as imidazole (hereinafter referred to as imidazoles), 4- (4,6-dimethoxy-1,3,5-triazin-2-yl) -4-methylmorphonium chloride n hydrate, trifluoro Triazines such as romethanesulfonic acid (4,6-dimethoxy-1,3,5-triazin-2-yl)-(2-octoxy-2-oxoethyl) dimethylammonium (hereinafter referred to as triazines), 1H— Benzotriazol-1-yloxytris (dimethylamino) phosphonium hexafluorophosphat
  • the reaction can be performed by adding a catalyst as necessary.
  • a catalyst include 1-hydroxybenzotriazole (hereinafter referred to as HOBt) and 1-hydroxyazabenzotriol (hereinafter referred to as HOAt).
  • the compound (R2) 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. Used in proportions.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be obtained by post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration of the organic layer.
  • Production method 3 The compound of the present invention can also be produced according to the following method.
  • Compound (M5) can be produced by reacting compound (R2) with compound (R1) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen carbonates, alkali metal hydroxides, alkaline earth metal hydroxides, metal alkoxides. And alkali metal hydrides.
  • the reaction can be performed by adding a catalyst as necessary.
  • the catalyst used in the reaction include dimethylaminopyridine.
  • compound (R1) is usually in a proportion of 1 to 2 mol
  • base is usually in a proportion of 1 to 2 mol
  • catalyst is usually in a proportion of 0.01 to 0.5 mol.
  • the reaction temperature is usually in the range of ⁇ 30 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • compound (M5) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • compound (M6) a method for producing a compound represented by formula (M6) from compound (M5) (hereinafter referred to as compound (M6)) will be described.
  • Compound (M6) can be produced by reacting compound (M5) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include water and a mixture of alcohols and water.
  • Examples of the base used in the reaction include alkali metal hydroxides and alkaline earth metal hydroxides.
  • the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M5).
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (M6) can be obtained by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent and drying and concentration of the organic layer.
  • the compound of the present invention can be produced by reacting the compound (M6) and the compound (M1) in the presence of a condensing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, nitrogen-containing aromatics such as pyridine and quinoline. Examples thereof include compounds (hereinafter referred to as nitrogen-containing aromatic compounds), water, and mixtures thereof.
  • condensing agent examples include carbodiimides, imidazoles, triazines, phosphoniums, and uroniums.
  • the reaction can be performed by adding a catalyst as necessary.
  • a catalyst examples include HOBt and HOAt.
  • the compound (M1) 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. Used in proportions.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Manufacturing method 4 The compound of the present invention can also be produced according to the following method.
  • the compound of the present invention can be produced by reacting compound (M1) with compound (M7) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkaline earth metal carbonates, alkali metal hydrogen carbonates, alkali metal hydroxides, alkaline earth metal hydroxides, metal alkoxides. And alkali metal hydrides.
  • the reaction can be performed by adding a catalyst as necessary.
  • the catalyst used in the reaction include dimethylaminopyridine.
  • compound (M7) is usually in a proportion of 0.5 to 2 mol
  • base is usually in a proportion of 1 to 2 mol
  • catalyst is usually in a proportion of 0.01 to 0.5 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of ⁇ 30 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound of the present invention can be obtained by post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (M7) can be produced by reacting compound (M6) with a chlorinating agent.
  • the reaction is performed in the presence or absence of a solvent.
  • a solvent used in the reaction include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • chlorinating agent used in the reaction examples include thionyl chloride, oxalyl chloride, phosphoryl chloride, sulfuryl chloride, phosphorus trichloride, and phosphorus pentachloride.
  • the chlorinating agent is usually used at a ratio of 1 to 100 mol per 1 mol of the compound (M6).
  • the reaction temperature is usually in the range of ⁇ 30 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (M7) can be obtained by post-treatment such as adding water to the reaction mixture and concentrating.
  • a compound represented by formula (1b) (hereinafter referred to as compound (1b)) and a compound represented by formula (1c) (hereinafter referred to as compound (1c)) can be produced by the following scheme. .
  • Compound (1b) can be produced by reacting compound (1a) with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • oxidizing agent used in the reaction examples include sodium periodate, m-chloroperbenzoic acid (hereinafter referred to as mCPBA), and hydrogen peroxide.
  • a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • Examples of the catalyst used in the reaction include tungstic acid and sodium tungstate.
  • the oxidizing agent is usually in a proportion of 1 to 1.2 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • Compound (1c) can be produced by reacting compound (1b) with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • oxidizing agent used in the reaction examples include mCPBA and hydrogen peroxide.
  • hydrogen peroxide a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • Examples of the catalyst used in the reaction include sodium tungstate.
  • the oxidizing agent is usually in a proportion of 1 to 4 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol.
  • the reaction temperature is usually in the range of ⁇ 20 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (1c) can be produced in a one-step reaction (one pot) by reacting the compound (1a) with an oxidizing agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • oxidizing agent used in the reaction examples include mCPBA and hydrogen peroxide.
  • a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • Examples of the catalyst used for the reaction include tungstic acid and sodium tungstate.
  • the oxidizing agent is usually in a proportion of 2 to 5 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol.
  • the reaction temperature is usually in the range of 0 to 120 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • a compound represented by formula (1e) (hereinafter referred to as compound (1e)) is produced by reacting a compound represented by formula (1d) (hereinafter referred to as compound (1d)) with an oxidizing agent. can do.
  • the reaction is usually performed in the presence of a solvent.
  • the solvent used in the reaction include aliphatic halogenated hydrocarbons, nitriles, alcohols, acetic acid, water, and mixtures thereof.
  • Examples of the oxidizing agent used in the reaction include sodium periodate, mCPBA, and hydrogen peroxide.
  • a base or a catalyst may be added as necessary.
  • sodium carbonate As the base used in the reaction, sodium carbonate can be mentioned.
  • Examples of the catalyst used for the reaction include tungstic acid and sodium tungstate.
  • the oxidizing agent is usually in a proportion of 1 to 1.2 mol
  • the base is usually in a proportion of 0.01 to 1 mol
  • the catalyst is usually in a proportion of 0.01 to 0.5 mol. It is used in the ratio.
  • the reaction temperature is usually in the range of ⁇ 20 to 80 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound represented by the formula (1f) (hereinafter referred to as the compound (1f)) can be produced by the following scheme.
  • the compound represented by the formula (1g) (hereinafter referred to as the compound (1g)) can be produced by the following scheme.
  • R 1a and E each independently represent a chlorine atom, a bromine atom or an iodine atom
  • R 2a represents a C1-C6 perfluoroalkyl group
  • R 4a and R 5a each independently represent C1 —C6 alkyl group or C1-C6 haloalkyl group, and other symbols have the same meanings as described above.
  • the compound represented by the formula (M8) (hereinafter referred to as the compound (M8)) is described in Journal of the American Chemical Society, 1931, vol. 53, p. It can be produced according to the method described in 3143-3146.
  • a compound represented by formula (M9) (hereinafter referred to as compound (M9)) can be produced by reacting compound (M8) with a compound represented by formula (R3) in the presence of a base. It can.
  • the reaction can be carried out according to the method described in, for example, International Publication No. 2003/024961.
  • the compound represented by the formula (M10) (hereinafter referred to as the compound (M10)) can be produced using the compound (M9) according to the method described in International Publication No. 2005/073165.
  • a compound represented by the formula (M11) (hereinafter referred to as compound (M11)) can be produced according to the method described in International Publication No. 2003/024961.
  • the compound represented by the formula (M12) (hereinafter referred to as the compound (M12)) is prepared according to the method for producing the compound (M2) from the compound (M1) described in the production method 1 using the compound (M11). Can be manufactured.
  • compound (M14) The compound represented by formula (M14) (hereinafter referred to as compound (M14)) can be produced according to the method described in production method 2 using compound (M12).
  • Compound (1g) can be produced by reacting compound (M14) with a compound represented by formula (R5) (hereinafter referred to as compound (R5)) in the presence of an additive.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aprotic polar solvents.
  • Examples of the additive used in the reaction include copper powder activated by the method described in Journal of Fluorine Chemistry, 102 (2000) 293-300.
  • the compound (R5) is usually used at a ratio of 1 to 10 moles, and the additive is usually used at a ratio of 1 to 10 moles.
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the additive is removed by filtration, water is added to the reaction mixture, extraction is performed with an organic solvent, and post-treatment operations such as drying and concentration of the organic layer are performed to obtain the compound (1 g). be able to.
  • Manufacturing method 10 Compound (1g) can be produced according to the following scheme.
  • the compound represented by the formula (M15) (hereinafter referred to as the compound (M15)) is obtained from the compound (M3) described in the production method 2 using the compound (M6) and the compound represented by the formula (R6). It can be produced according to the method for producing the inventive compound.
  • compound (M16) The compound represented by formula (M16) (hereinafter referred to as compound (M16)) was prepared according to the method for producing compound (M3) from compound (M2) described in production method 2 using compound (M15). Can be manufactured.
  • the compound represented by the formula (M17) (hereinafter referred to as the compound (M17)) is obtained from the compound (M3) described in the production method 2 using the compound (M16) and the compound represented by the formula (R7). It can be produced according to the method for producing the inventive compound.
  • the compound represented by the formula (R6) and the compound represented by the formula (R7) are commercially available compounds or can be produced according to known methods.
  • Compound (M18) can be produced by reacting compound (M17) and compound (R5) in the presence of an additive.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • Examples of the additive used in the reaction include dithionite such as sodium dithionite or zinc-sulfite water.
  • Examples of the base used in the reaction include organic bases, alkali metal carbonates, and alkali metal hydroxides.
  • phase transfer catalyst In the reaction, a phase transfer catalyst can be used as necessary.
  • the phase transfer catalyst used in the reaction include quaternary ammonium salts such as tetrabutylammonium hydrogen sulfate, organic phosphorus salts such as tetrabutylphosphonium bromide, and alkyl polyether alkylamine compounds such as tris (methoxyethoxyethyl) amine. Is mentioned.
  • compound (M17) is usually in a proportion of 1 to 10 mol
  • additive is usually in a proportion of 0.1 to 2 mol
  • base is usually in a proportion of 1 to 10 mol
  • a phase transfer catalyst is usually used at a ratio of 0.01 to 2 mol.
  • the reaction temperature is usually in the range of 0 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 48 hours.
  • the compound (M18) can be obtained by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (1g) can be produced by reacting compound (M18) with a halogenating agent.
  • the reaction is usually performed in the presence of a solvent.
  • a solvent examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, and mixtures thereof.
  • halogenating agent used in the reaction examples include N-chlorosuccinimide (hereinafter referred to as NCS), chlorine, N-bromosuccinimide (hereinafter referred to as NBS), bromine, and N-iodosuccinic acid.
  • NCS N-chlorosuccinimide
  • NBS N-bromosuccinimide
  • bromine N-iodosuccinic acid
  • examples include imide (hereinafter referred to as NIS), iodine and the like.
  • the halogenating agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (M18).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • the compound (1 g) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (R9) can be produced according to the method described in production method 8 using the compound represented by formula (R8) (hereinafter referred to as compound (R8)).
  • Compound (R10) can be produced according to the method described in Production Method 7 using Compound (R9).
  • Compound (R11) and Compound (R12) can be produced according to the method described in Production Method 6 using Compound (R8).
  • Compound (R8) is a commercially available compound or can be produced according to a known method.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 7a , R 6b , R 7b , R 6c , R 7c , R 6d , R 7d , Q and k are [Table 1] to The compound of the present invention which is a combination described in [Table 10].
  • R 6c , R 7c , R 6d and R 7d are hydrogen atoms
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 7a , R 6b , R 7b , Q and k are The compounds of the present invention which are combinations described in [Table 11] to [Table 18].
  • harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites. Specific examples of such harmful arthropods include the following.
  • Hemiptera pests Japanese brown planthoppers (Laodelphax striatellus), brown planthoppers (Nilaparvata lugens), white planthoppers (Sogatella furcifera), corn planters (Peregrinus maidis), etc.
  • Stinkbugs (Leptocorisa chinensis), Helicoptera helicopters (Leptocorisa acuta), Leptocorisa genus, etc. , Chinchi Bugs (Blissus leucopterus leucopterus) and other turtles, whitefly (Trialeurodes vaporariorum), tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), citrus whitefly (Aleurocanthus spiniferus San Jose scale insect (Comstockaspis perniciosa), citrus snow scale (Unaspis citri), ruby rot beetle (Ceroplastes rubens), Icerya scale insect (Icerya purchasi), Fujicona scale insect (Planococcus kraunhiae), staghorn beetle (Pseuocis) Pseudaulacaspis pentagona), scale insects such as Brevennia ⁇
  • Lepidoptera Chilo suppressalis, Darkheaded stm borer (Chilo polychrysus), Sunpikeza (Tryporyza incertulas), Netloi (Chilo polychrysus), White-meicho (Scirpophaga innotata), Yellow stem borer (Scirpophaga incertulas) Sesamia inferens, Rupela albinella, Cnaphalocrocis medinalis, Marasmia patnalis, Marasmia exigna, Notarcha derogata, Plodia interpunctella, Odalian Hula isla teterrellus), rice case worm (Nymphula depunctalis), Marasmia spp., Hop vine borer (Hydraecia immanis), European corn borer (Ostrinia nubilalis), Lesser cornstalk borer (Elasmopalpus lignosellus), Bean Shoot Borane (
  • Goats such as Velvetbean caterpillar (Anticarsia gammatalis) and Cotton leafworm (Alabama argillacea), white butterflies such as Pieris rapae, genus Adoxofies, Grapholita molesta, Leguminivora glycinivorella , Azukisayamushiga (Matsumuraeses azukivora), apple Coca summer fruit tortrix (Adoxophyes orana fasciata), smaller tea tortrix (Adoxophyes honmai.
  • Citrus thrips (Frankliniella occidentalis), Thrips peri, Scirtothrips dorsalis, Thrips tabaci Thrips such as Kapida thrips (Haplothrips aculeatus), Rice thrips (Stenchaetothrips biformis).
  • Diptera Culex pipiens pallens, Culex tritaeniorhynchus, Culex quinquefasciatus and other mosquitoes, Aedes ophegos Genus Anopheles, Chironomid, Musca domestica, Muscina stabulans, etc.
  • Agromyza oryzae rice leaflet (Hydrellia griseola), tomato leaffly (Liriomyza sativae), beetle leaflet (Liriomyza trifolii), leafhopper (Chromatomyia horticola) and other leafhoppers (Chromatomyia horticola), ryzae and other fruit fly, Dacus cucurbitae, fruit fly such as Ceratitis capitata, Hydrellia philippina, and Fleas such as fleas (Megaselia spiracularis), butterflies such as Clogmia albipunctata, and black fly flies.
  • Crane fly such as Hessian fly (Mayetiola destructor), Oreseolia oryzae, Crane fly such as Diopsis macrophthalma, Common cranefly (Tipula oleracea), European gantry such as Europeanopecranefly (Tipula paludosa).
  • Coleoptera Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica virgifera zeae), Banded cucumber beetle (Diabrotica virgifera zeae) , San Antonio beetle (Diabrotica speciosa), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), cereal leaf beetle (Oulema melanopus), cucumber horn beetle (Aulacophora) femoralis), pheasant potato beetle (Phylolsa ⁇ decor) , Rice beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flare beetle (Chaetocnema pulicaria), potato flare beetle (Epitrix
  • Insect pests Tosama locust (Locusta migratoria), Kera (Gryllotalpa africana),ixie flying grasshopper (Dociostaurus maroccanus), Australian flying grasshopper (Chortoicetes terminifera), Red-spotted grasshopper (Nomadacris septemfa ciaustal Locna, Loc) melanorhodon), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Twostriped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus sanguinipes) (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Coxenago (Oxya yezo
  • Hymenopteran pests bees such as Athalia rosae and Japanese bee (Athalia japonica). Fire Ants. Hachiriari such as Brown leaf-cutting ant (Atta capiguara).
  • Cockroach eye insects German cockroach (Blattella germanica), Black cockroach (Periplaneta fliginosa), American cockroach (Periplaneta americana), Great cockroach (Periplaneta brunnea), Great cockroach (Blatta orientalis).
  • Termite insect pests Yamato termite (Reticulitermes speratus), termite (Coptotermes formosanus), American ant termite (Incisitermes minor), daiko termite (Cryptotermes domesticus), ant-white termite (Odontotermes formosaterm), ants Glyptotermes satsumensis), long term termite (Glyptotermes miyatakei), white termite (Reticulitermes flaviceps amamianus), common termite (Reticulitermes sp.), white termite (Nasutitermes takasagoensis), nitobeshi Lori (Pericapritermes nitobei), Mushy termite (Sinocapritermes mushae), Cornitermes cumulans, etc.
  • Yamato termite Reticulitermes speratus
  • termite Coptotermes formosanus
  • American ant termite Inc
  • Nite spider mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai), Scarlet spider mite (Panonychus citri), Apple spider mite (Panonychus ulmi), Oligonicus spp.
  • 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
  • Acid amides (DMF, N, N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), sulfoxides (dimethylsulfoxide, etc.), propylene carbonate and vegetable oils (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.
  • Examples of 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. 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 in 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, a wettable powder, a flowable agent, etc., it is usually applied by diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm. Granules, powders and the like 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 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, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration 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.
  • Reference production example 4 1.37 mL of oxalyl chloride was added dropwise to a mixture of 2.74 g of 4-fluoro-3-nitrobenzoic acid, 0.1 mL of DMF and 30 mL of THF, and the mixture was stirred for 1 hour under reflux. The reaction mixture allowed to cool to room temperature was concentrated to give 4-fluoro-3-nitrobenzoyl chloride.
  • Reference production example 11 2.39 g of N-bromosuccinimide was added to a mixture of 3.0 g of 4- (trifluoromethoxy) -2- (trifluoromethyl) aniline, 25 mL of ethyl acetate and 5 mL of DMF, and the mixture was stirred at room temperature for 2.5 hours. To this reaction mixture was added 20% aqueous sodium thiosulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-bromo-4- (trifluoromethoxy) -6- (trifluoromethyl) aniline 3 0.2 g was obtained.
  • R 1 , R 3 and X a are represented by [Table 28].
  • R 1 , R 3 and X a are represented by [Table 29].
  • R 1 , R 3 and X a are represented by [Table 30] and [Table 31].
  • R 1 , R 3 and X a are represented by [Table 32] and [Table 33].
  • N-bromosuccinimide (59 mg) was added to a mixture of the compound of the present invention 1-1 (0.15 g), cyanamide (12 mg), tert-butoxypotassium (29 mg) and methanol (7 mL), and the mixture was stirred at room temperature for 5 hours.
  • a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate.
  • the obtained residue was subjected to silica gel column chromatography to obtain 0.13 g of the present compound 1-10 shown below.
  • Compound 1-10 of the present invention 60 mg was added to a mixture of the compound of the present invention 1-1 (0.15 g), cyanamide (12 mg), tert-butoxypotassium (29 mg) and methanol (7 mL), and the mixture was stirred at room temperature for 5 hours.
  • a saturated aqueous sodium thiosulfate solution was added to the reaction mixture, extracted
  • Production Example 8 The present compound 1-19 shown below was obtained according to the method described in Production Example 7 using the present compound 1-2 instead of the present compound 1-1.
  • T in the formula represents a substituent described in [Table 34] to [Table 36] below.
  • R 1 , R 3 , X 1 and n in the formula represent the combinations described in the following [Table 37] to [Table 40].
  • R 4 , R 5 and n in the formula represent the combinations described in [Table 41] below.
  • X a in the formula represents a combination described in [Table 42].
  • Formulation Example 1 10 parts of any one of compounds 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 of the present invention In a mixture of 35 parts of xylene and 35 parts of DMF, 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and mixed to obtain each preparation.
  • Formulation Example 2 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of a synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and the compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3 20 parts of any one of -1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 are added and mixed to obtain each wettable powder.
  • Formulation Example 3 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 Then, 1 part of synthetic silicon hydrous fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are added and mixed. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain each granule.
  • Formulation Example 4 One part of any one of the compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 Dissolve in an appropriate amount of acetone, add 5 parts of synthetic hydrous hydroxide fine powder, 0.3 part of isopropyl acid phosphate and 93.7 parts of fusami clay, stir and mix thoroughly, and evaporate and remove acetone to remove each powder. Get.
  • Formulation Example 5 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), and the compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7 Each flowable agent is obtained by mixing 10 parts of any one of 4-1 to 4-4, 5-1, and 6-1 and 55 parts of water and finely pulverizing them by a wet pulverization method.
  • Formulation Example 7 10 mg of any one of the compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 in acetone Dissolve in 0.5 mL and drop this solution into 5 g of animal solid feed powder (solid feed powder CE-2 for breeding, product of Nippon Claire Co., Ltd.) and mix uniformly. Then acetone is evaporated to dryness to obtain each poisonous bait.
  • animal solid feed powder solid feed powder CE-2 for breeding, product of Nippon Claire Co., Ltd.
  • Formulation Example 8 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 0.1 Part, neothiozole (manufactured by Chuo Kasei Co., Ltd.) 49.9 parts in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are added, shaken, and an actuator aerosol is attached by attaching an actuator. obtain.
  • neothiozole manufactured by Chuo Kasei Co., Ltd.
  • Formulation Example 9 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 0.6 Parts, BHT (2,6-di-tert-butyl-4-methylphenol) 0.01 part, xylene 5 parts, kerosene 3.39 parts and emulsifier ⁇ Rheodor MO-60 (manufactured by Kao Corporation) ⁇ 1 part After the mixture and 50 parts of distilled water are filled in an aerosol container and a valve is mounted, 40 parts of propellant (LPG) is pressurized and filled through the valve to obtain an aqueous aerosol.
  • LPG propellant
  • Formulation Example 10 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 0.1 g 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 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 5 parts Melt 95 parts of ethylene-methyl methacrylate copolymer (ratio of methyl methacrylate in the copolymer: 10% by weight, ACLIFT (registered trademark) WD301, manufactured by Sumitomo Chemical Co., Ltd.) with a closed pressure kneader (Moriyama Seisakusho) 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.
  • ACLIFT registered trademark
  • WD301 manufactured by Sumitomo Chemical Co., Ltd.
  • 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 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 5 parts 95 parts of a soft vinyl chloride resin is 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 to obtain a rod-shaped molded body having a length of 15 cm and a diameter of 3 mm. obtain.
  • a closed pressure kneader manufactured by Moriyama Seisakusho
  • Formulation Example 13 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 100 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 2.5 mg are mixed and the resulting mixture is Compress to size to obtain tablets.
  • Formulation Example 14 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 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 to obtain a capsule.
  • Formulation Example 15 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 100 mg, fumar Distilled to 500 mL of acid, 2000 mg of sodium chloride, 150 mg of methylparaben, 50 mg of propylparaben, 25000 mg of granular sugar, 13000 mg of sorbitol (70% solution), 100 mg of VeegumK (VanderbiltCo.), 35 mg of fragrance, and 500 mg of colorant to a final volume of 100 mL Add water and mix to obtain a suspension for oral administration.
  • Formulation Example 16 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 5% by weight Is dissolved in 5% by weight of polysorbate 85, 3% by weight of benzyl alcohol and 30% by weight of propylene glycol, and a phosphate buffer solution is added so that the pH of this solution is 6.0 to 6.5. Water is added as the balance to obtain a solution for oral administration.
  • 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.
  • any one of the compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 10 Distribute the weight percentage to obtain a paste preparation for oral administration.
  • Formulation Example 18 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 5% by weight Is mixed with 95% by weight of limestone powder to obtain granules for oral administration using the wet granulation method.
  • Formulation Example 19 5 parts of any one of compounds 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 of the present invention Dissolve in 80 parts of diethylene glycol monoethyl ether and mix with 15 parts of propylene carbonate to obtain a spot-on solution.
  • Formulation Example 20 10 parts of any one of compounds 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 of the present invention Dissolve in 70 parts of diethylene glycol monoethyl ether and mix with 20 parts of 2-octyldodecanol to obtain a pour-on solution.
  • Formulation Example 21 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 0.5 60 parts of Nikkor (registered trademark) TEALS-42 (42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine) and 20 parts of propylene glycol were added to the resulting mixture, and the mixture was stirred and mixed until a homogeneous solution was obtained. Add 5 parts and further stir and mix to obtain a shampoo of a uniform solution.
  • Nikkor registered trademark
  • TEALS-42 42% aqueous solution of Nikko Chemicals lauryl sulfate triethanolamine
  • Formulation Example 22 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 0.15
  • the animal feed premix is obtained by sufficiently stirring and mixing 4.85% by weight of a mixture consisting of dilute calcium phosphate, diatomaceous earth, Aerosil, and carbonate (or chalk).
  • Formulation Example 23 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1, and 6-1 7.2 g , 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 form, cooled and solidified to obtain a suppository.
  • Fosco registered trademark
  • S-55 manufactured by Maruishi Pharmaceutical Co., Ltd.
  • Test example 1 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-3, 2-7 to 2-9, 2-11 to 2-31, 3-1 to 3-7 obtained by Formulation Example 5
  • Formulations 4-1 to 4-3, 5-1, and 6-1 were each diluted with water so that the concentration of the compound of the present invention was 500 ppm to obtain a diluted solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • 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.
  • Test example 2 Compounds of the present invention 1-1 to 1-3, 1-5 to 1-8, 1-10, 1-12 to 1-14, 1-16, 1-20, 2-1 to 2-3, 2-7 to 2-9, 2-11, 2-12, 2-14, 2-15, 2-17 to 2-19, 2-21 to 2-25, 2-27 to 2-
  • the preparations of 29, 3-1 to 3-7, 4-2, 5-1 and 6-1 were diluted with water so that the concentration of the compound of the present invention was 200 ppm, respectively, to obtain a diluted solution.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • 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.
  • Test example 3 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-4, 2-7 to 2-11 to 2-31, 3-1 to 3-7, 4-1 to 4
  • the preparations 4-3 and 5-1 were each diluted with water so that the concentration of the compound of the present invention was 500 ppm to obtain a diluted solution.
  • the diluted solution was sprayed at a rate of 20 mL / cup on a three-leaf cabbage planted in a polyethylene cup. After spraying, the plants were air-dried, the stems and leaves were cut out and accommodated in a 50 mL cup, and 5 second-instar larvae (Plutella xylostella) were released and capped. After storing at 25 ° C., the number of dead insects was counted after 5 days, and the death rate was calculated from the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 80% or more in all the treatment areas where the compounds of the present invention were tested.
  • Test example 4 Compounds of the present invention 1-1 to 1-10, 1-12 to 1-15, 1-18, 1-20, 2-1 to 2-4, 2-7 to 2-9 obtained by Formulation Example 5
  • Formulations 2-11 to 2-19, 2-21 to 2-23, 2-25 to 2-29, 3-1 to 3-7, 4-1 to 4-3, and 5-1 are respectively represented in the present invention. It diluted with water so that the density
  • the diluted solution was sprayed at a rate of 20 mL / cup on a three-leaf cabbage planted in a polyethylene cup. After spraying, the plants were air-dried, the stems and leaves were cut out and accommodated in a 50 mL cup, and 5 second-instar larvae (Plutella xylostella) were released and capped. After storing at 25 ° C., the number of dead insects was counted after 5 days, and the death rate was calculated from the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 80% or more in all the treatment areas where the compounds of the present invention were tested.
  • Test Example 5 Compounds of the present invention 1-1 to 1-18, 2-20, 2-1 to 2-4, 2-7 to 2-9, 2-11 to 2-19, 2-21 to Formulations 2-29, 3-1 to 3-7, 4-1, 4-2 and 5-1 were each diluted with water so that the concentration of the compound of the present invention 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, in-sector LF (Nihon Nosan Co., Ltd.) sliced into 6 mm thickness and cut in half was placed, and 2 mL of the diluted solution was irrigated. After air drying, 5 third instar larvae of Spodoptera litura were released and covered. Six days later, the number of dead insects was counted, and the death rate was obtained from the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 80% or more in all the treatment areas where the compounds of the present invention were tested.
  • Test Example 6 Compounds of the present invention 1-1 to 1-18, 1-20, 2-1 to 2-3, 2-7 to 2-9, 2-11 to 2-29, 2-31 obtained by Formulation Example 5
  • the preparations of 3-1 to 3-7, 4-1 to 4-3, and 5-1 were each diluted with water so that the concentration of the compound of the present invention was 200 ppm to obtain a diluted solution.
  • the diluted solution was sprayed at a rate of 20 mL / cup on 5-6 leaf cabbage (Brassicae oleracea) planted in a polyethylene cup. After spraying, the plants were air-dried, covered with a polyethylene cup (capacity 400 mL), 10 4th instars of Spodoptera litura were released, and capped with Tetorongose. After storing at 25 ° C., the number of surviving insects was counted after 6 days, and the death rate was determined from the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 80% or more in all the treatment areas where the compounds of the present invention were tested.
  • Test Example 7 Compounds of the present invention 1-1 to 1-3, 1-5 to 1-10, 1-13, 1-14, 1-16, 1-17, 2-1, 2-2 obtained by Formulation Example 5 2-7 to 2-9, 2-11, 2-12, 2-17 to 2-19, 2-21, 2-23, 2-24, 2-26, 2-27 and 3-1 to 3- Each of the preparations 7 was diluted with water so that the concentration of the compound of the present invention was 500 ppm to obtain a diluted solution.
  • Control rate (%) 100 ⁇ ⁇ 1 ⁇ (number of surviving ticks in treated area) / (number of surviving ticks in untreated area) ⁇ As a result, a control rate of 90% or more was exhibited in all the treatment sections where the compounds of the present invention were tested.
  • Test Example 8 Compounds of the present invention 1-1 to 1-18, 2-1 to 2-3, 2-7 to 2-31, 3-1 to 3-3, 3-5, 3-6 obtained by Formulation Example 5 Formulations 4-1 to 4-3 and 5-1 were each diluted with water so that the concentration of the compound of the present invention 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, 0.7 mL of the diluted solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food.
  • Ten female fly (Musca domestica) females were released into the polyethylene cup and covered. One day later, the life and death of the house fly was investigated, the number of dead insects was counted, and the death rate was calculated by the following formula.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 100% in all the treatment sections where the compound of the present invention was tested.
  • Test Example 9 Compounds of the present invention 1-1 to 1-20, 2-1 to 2-31, 3-1 to 3-7, 4-1 to 4-4, 5-1 and 6-1 obtained by Formulation Example 5 Each preparation was diluted with water so that the concentration of the compound of the present invention was 500 ppm to obtain a diluted solution.
  • the diluted solution (0.7 mL) was added to ion-exchanged water (100 mL) (active ingredient concentration: 3.5 ppm). Twenty instar larvae of Culex pipiens pallens were released into the solution, and the number of dead insects was counted one day later, and the death rate was determined.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the mortality rate of 91% or more was shown in all the treatment sections where the compounds of the present invention were tested.
  • Test Example 10 Compound 1-2 of the present invention obtained by Formulation Example 5, 1-4 to 1-7, 1-9, 1-12 to 1-14, 1-18, 1-20, 2-1 to 2-3, 2-7 to 2-9, 2-11, 2-12, 2-14 to 2-16, 2-18, 2-19, 2-21, 2-22, 2-24 to 2-27, 3-
  • the preparations 1 to 3-3, 3-5 to 3-7, 4-1, and 5-1 were each diluted with water so that the concentration of the compound of the present invention 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, 0.7 mL of the diluted solution was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food.
  • Two adult male cockroaches (Blattalla germanica) were released into the polyethylene cup and covered. One day later, the number of dead insects was counted to determine the death rate.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, the death rate was 100% in all the treatment sections where the compound of the present invention was tested.
  • Comparative Test Example 1 The compound 1-4 of the present invention and the compound 1-22 described in International Publication No. 2012/164698 were tested in accordance with the method described in Test Example 1 above, and control when the compound 1-4 of the present invention was used was tested. The control value when using compound 1-22 was 29% or less, whereas the value was 100%.
  • Compound 1-4 of the present invention was tested in accordance with the method described in Test Example 1 above, and control when the compound 1-4 of the present invention was used was tested. The control value when using compound 1-22 was 29% or less, whereas the value was 100%.
  • Comparative test example 2 The compound 1-7 of the present invention and the compound 1-25 described in International Publication No. 2012/164698 were tested according to the method described in Test Example 1 except that the concentration of the active compound was 50 ppm. The control value when using the inventive compound 1-7 was 90% or more, whereas the control value when using the compound 1-25 was 29% or less. Compound 1-7 of the present invention
  • the compound of the present invention exhibits an excellent control effect against harmful arthropods.

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Abstract

L'invention concerne un composé qui présente un excellent effet d'élimination des arthropodes nuisibles. La présente invention concerne un composé 3-aminooxalylaminobenzamide représenté par la formule (1) qui a un excellent effet d'élimination des arthropodes nuisibles.
PCT/JP2016/056540 2015-03-06 2016-03-03 Composé 3-aminooxalylaminobenzamide et son utilisation pour lutter contre des arthropodes nuisibles WO2016143650A1 (fr)

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Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003011028A1 (fr) * 2001-08-01 2003-02-13 Nissan Chemical Industries, Ltd. Amides substitues et pesticides
RU2247716C2 (ru) * 2003-03-27 2005-03-10 Российский химико-технологический университет им. Д.И. Менделеева (РХТУ) Замещенные метил-n-амидооксамоил-n-фенил-d, l-аланинаты и их способы получения
JP2006306771A (ja) * 2005-04-28 2006-11-09 Mitsui Chemicals Inc 農園芸用殺虫剤
WO2010090282A1 (fr) * 2009-02-06 2010-08-12 アグロカネショウ株式会社 Dérivés de 3‑aminoxalylaminobenzamide et agents insecticides et miticides les contenant en tant que principe actif
WO2010089881A1 (fr) * 2009-02-06 2010-08-12 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide et pesticide/miticide contenant le dérivé en tant que principe actif
JP2011506504A (ja) * 2007-12-21 2011-03-03 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 動物寄生虫を防除するための有用な薬剤としてのアミノベンズアミド誘導体
WO2012020484A1 (fr) * 2010-08-11 2012-02-16 アグロカネショウ株式会社 Dérivé de 3-aminooxalyl aminobenzanilide, et insecticide et acaricide utilisant celui-ci comme matière active
WO2012020483A1 (fr) * 2010-08-11 2012-02-16 アグロカネショウ株式会社 Dérivé de 3-aminooxalyl aminobenzamide, et insecticide et acaricide utilisant celui-ci comme matière active
WO2012042608A1 (fr) * 2010-09-29 2012-04-05 アグロカネショウ株式会社 Dérivé d'acide 3-aminobenzoïque et son procédé de production
WO2012077221A1 (fr) * 2010-12-10 2012-06-14 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide et agent insecticide et acaricide l'incluant en tant que principe actif
WO2012164698A1 (fr) * 2011-06-01 2012-12-06 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide, et agent insecticide ou miticide comprenant celui-ci en tant que substance active
JP2013256522A (ja) * 2008-08-13 2013-12-26 Mitsui Chemicals Agro Inc 新規な化合物
WO2014069665A1 (fr) * 2012-11-05 2014-05-08 三井化学アグロ株式会社 Composition pour extermination de parasites animaux et procédé d'extermination de parasites animaux

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003011028A1 (fr) * 2001-08-01 2003-02-13 Nissan Chemical Industries, Ltd. Amides substitues et pesticides
RU2247716C2 (ru) * 2003-03-27 2005-03-10 Российский химико-технологический университет им. Д.И. Менделеева (РХТУ) Замещенные метил-n-амидооксамоил-n-фенил-d, l-аланинаты и их способы получения
JP2006306771A (ja) * 2005-04-28 2006-11-09 Mitsui Chemicals Inc 農園芸用殺虫剤
JP2011506504A (ja) * 2007-12-21 2011-03-03 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 動物寄生虫を防除するための有用な薬剤としてのアミノベンズアミド誘導体
JP2013256522A (ja) * 2008-08-13 2013-12-26 Mitsui Chemicals Agro Inc 新規な化合物
WO2010090282A1 (fr) * 2009-02-06 2010-08-12 アグロカネショウ株式会社 Dérivés de 3‑aminoxalylaminobenzamide et agents insecticides et miticides les contenant en tant que principe actif
WO2010089881A1 (fr) * 2009-02-06 2010-08-12 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide et pesticide/miticide contenant le dérivé en tant que principe actif
WO2012020484A1 (fr) * 2010-08-11 2012-02-16 アグロカネショウ株式会社 Dérivé de 3-aminooxalyl aminobenzanilide, et insecticide et acaricide utilisant celui-ci comme matière active
WO2012020483A1 (fr) * 2010-08-11 2012-02-16 アグロカネショウ株式会社 Dérivé de 3-aminooxalyl aminobenzamide, et insecticide et acaricide utilisant celui-ci comme matière active
WO2012042608A1 (fr) * 2010-09-29 2012-04-05 アグロカネショウ株式会社 Dérivé d'acide 3-aminobenzoïque et son procédé de production
WO2012077221A1 (fr) * 2010-12-10 2012-06-14 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide et agent insecticide et acaricide l'incluant en tant que principe actif
WO2012164698A1 (fr) * 2011-06-01 2012-12-06 アグロカネショウ株式会社 Dérivé de 3-aminooxalylaminobenzamide, et agent insecticide ou miticide comprenant celui-ci en tant que substance active
WO2014069665A1 (fr) * 2012-11-05 2014-05-08 三井化学アグロ株式会社 Composition pour extermination de parasites animaux et procédé d'extermination de parasites animaux

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