WO2016163379A1 - Composé amide d'oxalyle et son utilisation pour la régulation d'arthropodes nuisibles - Google Patents

Composé amide d'oxalyle et son utilisation pour la régulation d'arthropodes nuisibles Download PDF

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WO2016163379A1
WO2016163379A1 PCT/JP2016/061210 JP2016061210W WO2016163379A1 WO 2016163379 A1 WO2016163379 A1 WO 2016163379A1 JP 2016061210 W JP2016061210 W JP 2016061210W WO 2016163379 A1 WO2016163379 A1 WO 2016163379A1
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atom
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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
    • A01N43/74—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to certain oxalamide compounds and their use for harmful arthropods.
  • 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.
  • J 1 , J 2 , J 3 and J 4 each independently represent a nitrogen atom or CR 6 (provided that at least one of J 1 , J 2 , J 3 and J 4 represents a nitrogen atom), R 1 and R 3 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, —R 7 , —OR 7 or —S (O) p R 7 ; R 2 represents —R 7 , —OR 7 or —S (O) p R 7 , Each X independently represents —R 7 , —OR 7 , a halogen atom or a cyano group; R 4 and R 5 are each independently a hydrogen atom, —R 7 , (C1-C4 alkoxy) C1-C4 alkyl group, —C (O) R 7 or —CO 2 represents R 7 , R 6 represents a hydrogen atom, a halogen atom, —R 8 or —OR
  • R 11 represents a hydrogen atom, —R 7 , —C (O) R 7 , —CO 2 R 7 or SO 2 R 7
  • R 12 represents a hydrogen atom, a cyano group, or a C1-C6 alkyl group which may have one or more halogen atoms
  • k represents 0, 1 or 2
  • m represents 0 or 1
  • the sum of k and m represents 0, 1 or 2
  • n and p each independently represent 0, 1 or 2.
  • An oxalylamide compound represented by formula hereinafter also referred to as the present compound).
  • R 1 and R 3 are bromine atom, an iodine atom or a C1-C6 alkyl group, and the other is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C1-C6 haloalkoxy group,
  • a harmful arthropod control composition comprising the compound according to any one of [1] to [7] 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 [7] to harmful arthropods or habitats of harmful arthropods.
  • 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.
  • CX-CY means that the number of carbon atoms is X to Y.
  • C1-C6 means that the number of carbon atoms is 1 to 6
  • C1-C3 means that the number of carbon atoms is 1 to 3.
  • examples of the “C1-C6 alkyl group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a 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 “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, for example, a fluoromethyl group, a difluoromethyl group, a trifluoro Methyl group, chlorodifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, heptafluoropropyl group, or heptafluoroisopropyl group, 1,1,2,2,3,3-hexafluoropropyl Groups, 2,2,2-trifluoro-1- (trifluoromethyl) ethyl group and trichloromethyl group.
  • a fluoromethyl group for example, a fluoromethyl group, a difluoromethyl group, a trifluoro Methyl group, chlorodifluoromethyl group, 2,2,2-trifluoro
  • 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, Fluoromethoxy group, chlorodifluoromethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, heptafluoropropoxy group, or heptafluoroisopropoxy group, 1,1,2,2,3,3-hexa Examples thereof include a fluoropropoxy group, 2,2,2-trifluoro-1- (trifluoromethyl) ethoxy group, and trichloromethoxy group.
  • a fluoromethoxy group such as a fluoromethoxy group, a difluoromethoxy group, Fluoromethoxy group, chlorodifluoromethoxy group, 2,2,2-trifluoroethoxy group,
  • the “C1-C6 haloalkylthio group” is a monovalent group in which the “C1-C6 haloalkyl group” is bonded to a sulfur atom, and the “C1-C6 haloalkylsulfinyl group” is the above “C1 The —C6 haloalkyl group ”is a monovalent group bonded to the sulfur atom of S (O), and the“ C1-C6 haloalkylsulfonyl group ”means that the“ C1-C6 haloalkyl group ”is sulfur of S (O) 2 A monovalent group bonded to an atom.
  • halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
  • halogen atoms may be the same or different from each other.
  • chain hydrocarbon group means an alkyl group, an alkenyl group, or an alkynyl group.
  • C1-C6 chain hydrocarbon group means a C1-C6 alkyl group, a C2-C6 alkenyl group, and a C2-C6 alkynyl group.
  • the “C1-C6 chain hydrocarbon group” includes a C1-C3 chain hydrocarbon group.
  • C1-C6 alkyl group is as described above, and examples of the “C2-C6 alkenyl group” include vinyl group, allyl group, isopropenyl group, crotyl group, and “C2-C6 alkynyl group”. Examples of the “group” include an ethynyl group and a propargyl group.
  • C1-C6 chain hydrocarbon group optionally having one or more halogen atoms refers to a C1-C6 chain hydrocarbon group or a C1-C6 chain formula having one or more halogen atoms.
  • a hydrocarbon group is meant.
  • the “C1-C6 chain hydrocarbon group having one or more halogen atoms” means a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, and a C2-C6 haloalkynyl group.
  • the “C1-C6 haloalkyl group” is as described above, and the “C2-C6 haloalkenyl group” is a group in which one or more hydrogen atoms of the “C2-C6 alkenyl group” are substituted with a halogen atom.
  • the “C2-C6 haloalkynyl group” is a group in which one or more hydrogen atoms of the “C2-C6 alkynyl group” are substituted with a halogen atom.
  • (C1-C4 alkoxy) C1-C4 alkyl group optionally having one or more halogen atoms means that one hydrogen atom of the “C1-C4 alkyl group” is “one or more A group substituted with a “C1-C4 alkoxy group optionally having a halogen atom”, for example, a methoxymethyl group, an ethoxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, 2- (2,2, 2-trifluoroethoxy) ethyl group.
  • the oxalylamide compound represented by formula (I) according to the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in the structural formula, and two or more optical isomers may be present. Although present in some cases, the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio.
  • the oxalylamide compound represented by the formula (I) according to the present invention has two or more geometric isomers derived from a carbon-carbon double bond, a sulfur-nitrogen double bond, a cyclic structure, etc. in the structure. However, the present invention includes all the geometric isomers and the mixtures in which they are contained in an arbitrary ratio.
  • R 1 and R 3 are each independently a hydrogen atom, a halogen atom, —R 7 , —OR 7 or —S (O) p
  • R 7 , R 4 and R 5 are each independently a hydrogen atom or —R 7
  • R 7 is a C1-C3 chain hydrocarbon group which may have one or more halogen atoms
  • R 8 is a methyl group
  • a compound wherein n is 0.
  • a compound wherein any one of J 1 , J 2 , J 3 and J 4 is a nitrogen atom and the other is CR 6 .
  • any one of G 2 , G 3 , G 4 and G 5 is —S (O) k (Q) —, and the others are —CR 9 R 10 —, —C ( O)-or a compound that is a single bond.
  • any one of G 2 , G 3 , G 4 and G 5 is —O—, and the other is —CR 9 R 10 —, —C (O) — or a single bond A compound.
  • any one of G 2 , G 3 , G 4 and G 5 is —NR 11 —, and the others are —CR 9 R 10 —, —C (O) — or a single bond A compound that is [Aspect 18] A compound in which G 3 , G 4 and G 5 are a single bond in Aspects 1 to 14.
  • G 1 and G 6 are each independently —CR 9 R 10 —.
  • G 2 , G 3 , G 4 and G 5 are each independently -CR 9 R 10- , -S (O) k (Q) m- , -O- or a single bond (provided that G 2 , at least one of G 3 , G 4 and G 5 represents —S (O) k (Q) m — or —O—.
  • a plurality of R 9 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms;
  • a plurality of R 10 are each independently a hydrogen atom or a C1-C3 alkyl group optionally having one or more halogen atoms;
  • R 11 is a C1-C3 alkyl group, A compound wherein R 12 is a cyano group.
  • G 2 , G 3 , G 4 and G 5 are each independently -CR 9 R 10- , -S (O) k (Q) m- , -O- or a single bond (provided that G 2 , at least one of G 3 , G 4 and G 5 represents —S (O) k (Q) m — or —O—.
  • a plurality of R 9 are each independently a hydrogen atom, a methyl group or a trifluoromethyl group;
  • a plurality of R 10 are each independently a hydrogen atom, a methyl group or a trifluoromethyl group;
  • R 11 is a C1-C3 alkyl group, A compound wherein R 12 is a cyano group.
  • R 1 and R 3 are each independently a C1-C6 alkyl group optionally substituted with one or more halogen atoms, and a C1-C6 alkoxy group optionally substituted with one or more halogen atoms. Or a halogen atom, A compound in which R 2 is a C1-C6 haloalkyl group and n is 0.
  • R 1 and R 3 are each independently a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C1-C6 alkoxy optionally substituted with one or more halogen atoms.
  • R 1 and R 3 are each independently a C1-C6 alkyl group optionally substituted with one or more halogen atoms, or a C1-C6 alkoxy optionally substituted with one or more halogen atoms.
  • R 1 is a bromine atom, an iodine atom or a C1-C6 alkyl group
  • R 3 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group
  • R 1 is a bromine atom, an iodine atom or a C1-C6 alkyl group
  • R 3 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group
  • R 1 is a bromine atom, an iodine atom or a C1-C6 alkyl group
  • R 3 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 haloalkoxy group
  • a compound wherein R 2 is a C1-C6 perfluoroalkyl group and n is 0.
  • R 4 and R 5 are each independently a hydrogen atom or a C1-C3 alkyl group.
  • the compound wherein R 4 and R 5 are each independently a hydrogen atom or a C1-C3 alkyl group.
  • Aspect 46 Aspect 26 to 44, wherein any one of J 1 , J 2 , J 3 and J 4 is a nitrogen atom and the other is CH.
  • Aspect 47 Aspect 26 to aspect 44, wherein J 1 is a nitrogen atom, and J 2 , J 3 and J 4 are CH.
  • Aspect 48 Aspect 26 to aspect 44, wherein J 3 is a nitrogen atom, and J 1 , J 2 and J 4 are CH.
  • the compound of the present invention and the intermediate compound can be produced, for example, according to the following production methods 1 to 4.
  • Compound (M3) can be produced by reacting compound (M1) with a compound represented by formula (M2) (hereinafter referred to as compound (M2)) in the presence of a base.
  • Compound (M1) can be produced according to the method described in JP-A-2001-122836.
  • Compound (M2) can be a commercially available compound or can be produced according to a known method.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction 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, ethylene glycol dimethyl ether, methyl tert-butyl ether (hereinafter referred to as MTBE), 1,4-dioxane (hereinafter referred to as ethers); acetone, ethyl methyl ketone, isobutyl methyl ketone, etc.
  • Ketones 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), N-methylpi Pyrrolidone, aprotic polar solvents such as dimethyl sulfoxide (hereinafter, referred to as aprotic polar solvents.); And mixtures thereof.
  • 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 side and sodium ethoxide (hereinafter referred to as metal alkoxides); alkali metal hydr
  • the compound (M2) is usually used in a proportion of 1 to 2 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound (M1).
  • the reaction temperature of the reaction is usually in the range of ⁇ 80 to 150 ° C.
  • the reaction time is usually in the range of 0.1 to 12 hours.
  • Compound (M11) can be produced by reducing compound (M3).
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include ethers, esters, alcohols such as methanol, ethanol, and isopropanol (hereinafter referred to as alcohols), acetic acid, water, and mixtures thereof.
  • Examples of the reducing agent used in the reaction include iron and tin chloride.
  • an acid can be used as necessary.
  • the acid used for the reaction include acetic acid, hydrochloric acid, ammonium chloride and the like.
  • the reducing agent is usually used at a ratio of 3 to 10 mol per 1 mol of the compound (M3).
  • the reaction temperature of the reaction is usually in the range of 20 to 100 ° C.
  • the reaction time is usually in the range of 0.1 to 24 hours.
  • Compound (M4) can be produced according to the method described in International Publication No. 2003/024961. Next, it describes about the 4th process which manufactures the compound (henceforth a compound (M5)) represented by a formula (M5) from a compound (M4).
  • Compound (M5) can be produced by reacting compound (M4) with a compound represented by formula (R1) (hereinafter referred to as compound (R1)) in the presence of a base.
  • compound (R1) is a commercially available compound.
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction 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, and alkaline earth metal hydroxides.
  • the compound (R1) is usually used in a proportion of 1 to 2 mol and the base is usually used in a proportion of 1 to 2 mol with respect to 1 mol of the compound (M4).
  • 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 (I) can be produced by reacting compound (M5) with a compound represented by formula (R2) (hereinafter referred to as compound (R2)).
  • the reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples include aliphatic halogenated hydrocarbons, nitriles, ethers, ketones, esters, aromatic hydrocarbons, aprotic polar solvents, alcohols, water, and mixtures thereof. Can be mentioned.
  • 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 at a ratio of 1 to 10 moles, and the base is usually used at a ratio of 1 to 10 moles.
  • 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.
  • Manufacturing method 2 Compound (I) can also be produced according to the following method.
  • Compound (M6) can be produced by hydrolyzing compound (M5) in the presence of a base.
  • the reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include water, 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.
  • Compound (I) can be produced by reacting compound (M6) and compound (R2) in the presence of a condensing agent.
  • Examples of the solvent used in the reaction 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 (hereinafter referred to as carbodiimides); imidazoles such as N, N′-carbonyldiimidazole (hereinafter referred to as “carbodiimide”). O- (7-azabenzotriazol-1-yl) -N, N, N ′, N′-tetramethyluronium hexafluorophosphate (hereinafter referred to as HATU), etc.
  • Uroniums hereinafter referred to as uroniums).
  • 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.
  • Production method 3 Compound (I) can also be produced according to the following method.
  • the method for producing a compound represented by the formula (M8) from the compound (R2) (hereinafter referred to as compound (M8)) can be carried out according to the method described in the first step of production method 1. .
  • a method for producing a compound represented by the formula (M9) from the compound (M8) (hereinafter referred to as compound (M9)) can be carried out according to the method described in the first step of production method 2. .
  • the method for producing compound (I) from compound (M9) can be carried out according to the method described in the second step of production method 2.
  • Manufacturing method 4 Compound (I) can be produced by reacting compound (M4) with a compound represented by formula (M10) (hereinafter referred to as compound (M10)) in the presence of a base.
  • Compound (M10) can be produced by reacting compound (M9) with a chlorinating agent.
  • the reaction is performed in the presence or absence of a solvent.
  • the 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 (M9).
  • 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 (M10) can be obtained by post-treatment such as concentration of the reaction mixture.
  • 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 (I b) can be produced by reacting compound (I a) 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. Used in molar proportions.
  • 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 (Ic) can be produced by reacting compound (Ib) 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. Used in proportions.
  • 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 (Ic) can be produced in a one-step reaction (one pot) by reacting the compound (Ic) with an oxidizing agent.
  • the reaction can be carried out according to the method for producing compound (I c) from compound (I b) in Production Method 6 except that the oxidizing agent is 2 to 5 mol.
  • the method described in production method 6 is not limited to the case where G 3 is a sulfur atom, and oxidation can be performed by the same method when G 2 , G 4, or G 5 is a sulfur atom. it can.
  • the compound represented by the formula (I e) can be produced by reacting a compound represented by the formula (Id) (hereinafter referred to as the compound (Id)) with an oxidizing agent.
  • G 3 is -S (Q) - it is not limited to the case where, G 2, G 4 or G 5 is -S (Q) - be a similar It can be oxidized by this method.
  • Manufacturing method 8 Compound (Id) can be produced by the following scheme.
  • a compound represented by the formula (If) (hereinafter referred to as compound (If)) can be produced by the following scheme.
  • R 1a represents 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 a C1-C6 alkyl group or C1 —C6 represents a haloalkyl group, and other symbols have the same meanings as described above.
  • compound (M12) is Journal of the American Chemical Society, 1931, vol. 53, p. It can be produced according to the method described in 3143-3146.
  • the compound represented by the formula (M13) (hereinafter referred to as the compound (M13)) can be produced by reacting the compound (M12) and the compound represented by the formula (R4) 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 (M14) (hereinafter referred to as the compound (M14)) can be produced using the compound (M13) according to the method described in International Publication No. 2005/073165.
  • a compound represented by the formula (M15) (hereinafter referred to as compound (M15)) can be produced according to the method described in International Publication No. 2003/024961.
  • the compound represented by formula (M16) (hereinafter referred to as compound (M16)) can be produced according to the method described in the fourth step of production method 1, using compound (M15).
  • a compound represented by formula (M17) (hereinafter referred to as compound (M17)) can be produced according to the method described in the first step of production method 2 using compound (M16).
  • a compound represented by formula (M18) (hereinafter referred to as compound (M18)) can be produced according to the method described in the second step of production method 2, using compound (M17).
  • Compound (If) can be produced by reacting compound (M18) with a compound represented by formula (R6) (hereinafter referred to as compound (R6)) 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 (R6) is usually used in a proportion of 1 to 10 mol, and the additive is usually used in a proportion of 1 to 10 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.
  • a compound represented by the formula (Ig) (hereinafter referred to as compound (Ig)) can be produced by the following scheme.
  • a compound represented by formula (M19) (hereinafter referred to as compound (M19)) is produced using compound (M9) and a compound represented by formula (R7) (hereinafter referred to as compound (R7)). It can be produced according to the method described in the second step of Method 2.
  • the compound represented by the formula (M20) (hereinafter referred to as the compound (M20)) can be produced using the compound (M19) according to the method described in the first step of production method 2.
  • a compound represented by formula (M21) (hereinafter referred to as compound (M21)) is produced using compound (M20) and a compound represented by formula (R8) (hereinafter referred to as compound (R8)). It can be produced according to the method described in the second step of Method 2.
  • Compound (R7) and compound (R8) are commercially available compounds or can be produced according to known methods.
  • Compound (M22) can be produced by reacting compound (M21) and compound (R6) 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 alkylpolyetheralkylamine compounds such as tris (methoxyethoxyethyl) amine. Is mentioned.
  • compound (M21) 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 in a proportion 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 (M22) 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 (Ig) can be produced by reacting compound (M22) 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 (M22).
  • 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.
  • compound (I g) can be obtained by adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
  • Compound (R10) can be produced according to the method described in production method 8 using the compound represented by formula (R9) (hereinafter referred to as compound (R9)).
  • Compound (R11) can be produced according to the method described in Production Method 7 using Compound (R10).
  • Compound (R12) and Compound (R13) can be produced according to the method described in Production Method 6 using Compound (R9).
  • Compound (R9) can be a commercially available compound or can be produced according to a known method.
  • 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.
  • T is represented by [Table 1] and [Table 2].
  • R 1 and R 3 are represented by [Table 3].
  • R 1 and R 3 are represented by [Table 4].
  • R 1 and R 3 are represented by [Table 5].
  • R 1 and R 3 are represented by [Table 6] and [Table 7].
  • NBS 0.11 g was added to a mixture of the present compound 2a-1 (0.28 g), cyanamide 22 mg, tert-butoxypotassium 55 mg and methanol 14 mL, and the mixture was stirred at room temperature for 3 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 0.27 g of the present compound 2a-4 shown below.
  • E in the formula represents a substituent described in [Table 8] below.
  • E in the formula represents a substituent described in [Table 9] below.
  • E in the formula represents a substituent described in [Table 10] below.
  • E in the formula represents a substituent described in [Table 11] below.
  • Formulation Example 1 10 parts of any one of the present compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 synthetic silicon hydroxide fine powder and 54 parts of diatomaceous earth are mixed, and the compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a of the present invention are further mixed. -1 to 2a-12, 2b-1, 2c-1, 2c-2, and 2d-1 20 parts are added and mixed to obtain each wettable powder.
  • Formulation Example 3 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-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 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-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 (weight ratio 1: 1) of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon, and compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12 of the present invention
  • Each flowable agent is obtained by mixing 10 parts of any one of 2b-1, 2c-1, 2c-2 and 2d-1 and 55 parts of water and finely pulverizing them by a wet pulverization method.
  • Formulation Example 7 Compounds of the present invention 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 of the present invention 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 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-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 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 12 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-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 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 60 mg, corn starch 25 mg, carmellose calcium 6 mg, and 5% hydroxypropylmethylcellulose proper amount are mixed, and the obtained mixture is filled into a hard shell gelatin capsule or hydroxypropylmethylcellulose capsule to obtain a capsule.
  • Formulation Example 15 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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.
  • 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
  • Formulation Example 16 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2, and 2d-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. To this, any one of the compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 10 Distribute the weight percentage to obtain a paste preparation for oral administration.
  • Formulation Example 18 Compound 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2, and 2d-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 the present compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 the present compounds 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 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 22 Compounds of the present invention 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 Any one of 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 1a-1 to 1a-5, 1b-1, 1b-2, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 Any one kind 7.2g , 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 Formulations of the compounds 1a-1 to 1a-4, 2a-1 to 2a-12, 1b-1, 1b-2, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 Each was 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 Formulations of the compounds 1a-1 to 1a-5, 2a-1 to 2a-12, 1b-1, 1b-2, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 Each 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 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, in all treatment sections where the present compounds 1a-1 to 1a-5, 2a-1 to 2a-12, 1b-1, 1b-2, 2c-1, 2c-2 or 2d-1 were tested. The death rate was 80% or more.
  • Test example 3 Compounds of the present invention 1a-1, 1a-4, 1a-5, 2a-1 to 2a-4, 2a-6 to 2a-12, 1b-1, 2b-1, 2c- obtained according to Formulation Example 5
  • the preparations 1, 2c-2 and 2d-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
  • Test example 4 The compounds of the present invention 1a-1 to 1a-5, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 are each compound of the present invention.
  • the resulting solution was diluted with water so that the concentration thereof became 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 mortality rate was measured in all treatments where the compounds 1a-1 to 1a-5, 2a-1 to 2a-12, 2b-1, 2c-1, 2c-2 or 2d-1 were tested. It showed 80% or more.
  • Test Example 5 Compounds of the present invention 1a-1, 1a-4, 1a-5, 2a-1 to 2a-12, 1b-1, 1b-2, 2b-1, 2c-1, 2c- obtained according to Formulation Example 5
  • the preparations 2 and 2d-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 compound 1a-1, 1a-4, 1a-5, 2a-1 to 2a-12, 1b-1, 1b-2, 2b-1, 2c-1, 2c-2 or 2d-1 In all treatment sections tested, a mortality rate of 100% was shown.
  • Test Example 6 Compounds of the present invention 1a-1 to 1a-5, 2a-1 to 2a-4, 2a-6 to 2a-12, 1b-1, 1b-2, 2b-1, 2c- obtained according to Formulation Example 5
  • the preparations 1, 2c-2 and 2d-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 (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
  • Test Example 7 Formulations of the present compounds 2a-1 to 2a-3, 2a-6 to 2a-12, 1b-1, 2b-1, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 Each was diluted with water so that the concentration of the compound of the present invention was 200 ppm to obtain a diluted solution.
  • 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 parasitic live insects at the time of survey in the untreated group
  • Tb number of insects before the treatment in the treated group
  • Tai number of parasitic insects at the time of survey in the treated group
  • the untreated group means a group in which a preparation obtained by diluting the preparation not containing the compound of the present invention in Preparation Example 5 with the same amount of water as the treated group was sprayed.
  • Test Example 8 Formulations of the compounds 1a-4, 1a-5, 2a-1 to 2a-12, 1b-2, 2b-1, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 Each was 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 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, in all the treatment sections where the present compounds 1a-4, 1a-5, 2a-1 to 2a-12, 1b-2, 2b-1, 2c-1, 2c-2 or 2d-1 were tested. The death rate was 80% or more.
  • Test Example 9 Formulations of the present compounds 1a-4, 2a-1 to 2a-8, 2a-11, 1b-2, 2b-1, 2c-1, 2c-2 and 2d-1 obtained according to Formulation Example 5 Each 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) ⁇
  • the control rate was 90% or more.
  • Test Example 10 The preparations of the compounds of the present invention 2a-1 to 2a-4, 2a-7 to 2a-9, 2a-11, 2b-1, 2c-1 and 2d-1 obtained according to Formulation Example 5 are respectively represented in the present invention. It diluted with water so that the density
  • 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 mortality rate was measured in all treatments where the compounds 2a-1 to 2a-4, 2a-7 to 2a-9, 2a-11, 2b-1, 2c-1 or 2d-1 were tested. 100%.
  • the compound of the present invention exhibits an excellent control effect against harmful arthropods.

Abstract

La présente invention concerne un composé qui fait preuve d'un excellent effet de régulation des arthropodes nuisibles. Le composé amide d'oxalyle représenté par la formule (I) présente une excellente efficacité de régulation des arthropodes nuisibles (dans la formule, J1, J2, J3, et J4 représentent chacun indépendamment un atome d'azote ou similaire, R1 et R3 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, -R7, ou similaires, R2 représente -R7 ou similaire, chaque X représente indépendamment -R7, un atome d'halogène, ou similaires, R4 et R5 représentent chacun indépendamment un atome d'hydrogène, -R7, ou similaires, R7 représente un groupe hydrocarbure à chaîne en C1 à C6 qui peut avoir un ou plusieurs atomes d'halogène, G1 et G6 représentent chacun indépendamment -CR9R10- ou similaires, G2, G3, G4, et G5 représentent chacun indépendamment -S(O)k(Q)m-, -O-, ou similaires, R9 et R10 représentent chacun indépendamment un atome d'hydrogène, -R7, ou similaires, et n représente 0, 1, ou 2).
PCT/JP2016/061210 2015-04-09 2016-04-06 Composé amide d'oxalyle et son utilisation pour la régulation d'arthropodes nuisibles WO2016163379A1 (fr)

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JPS6084250A (ja) * 1983-08-26 1985-05-13 チバ−ガイギ−　アクチエンゲゼルシヤフト しゆう酸アニリド、その製造方法及び有害生物を防除するためのその使用方法
WO2003011028A1 (fr) * 2001-08-01 2003-02-13 Nissan Chemical Industries, Ltd. Amides substitues et pesticides
WO2004049803A1 (fr) * 2002-12-03 2004-06-17 Bayer Cropscience S.A. Derives pesticides de 5-(acylamino) pyrazole
JP2006306771A (ja) * 2005-04-28 2006-11-09 Mitsui Chemicals Inc 農園芸用殺虫剤
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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
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
JP2010248273A (ja) * 2010-08-10 2010-11-04 Nippon Soda Co Ltd オキシム化合物またはその塩、ならびに殺菌剤
JP2011510090A (ja) * 2008-01-22 2011-03-31 ダウ アグロサイエンシィズ エルエルシー ５−フルオロピリミジン誘導体
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
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
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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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6084250A (ja) * 1983-08-26 1985-05-13 チバ−ガイギ−　アクチエンゲゼルシヤフト しゆう酸アニリド、その製造方法及び有害生物を防除するためのその使用方法
WO2003011028A1 (fr) * 2001-08-01 2003-02-13 Nissan Chemical Industries, Ltd. Amides substitues et pesticides
WO2004049803A1 (fr) * 2002-12-03 2004-06-17 Bayer Cropscience S.A. Derives pesticides de 5-(acylamino) pyrazole
JP2006306771A (ja) * 2005-04-28 2006-11-09 Mitsui Chemicals Inc 農園芸用殺虫剤
CN1986533A (zh) * 2007-01-11 2007-06-27 中国农业科学院植物保护研究所 烯酰胺类簇合物的制备与应用
JP2011510090A (ja) * 2008-01-22 2011-03-31 ダウ アグロサイエンシィズ エルエルシー ５−フルオロピリミジン誘導体
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
JP2010248273A (ja) * 2010-08-10 2010-11-04 Nippon Soda Co Ltd オキシム化合物またはその塩、ならびに殺菌剤
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
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
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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