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WO2014178363A1 - Dérivé de diamide, pesticide à usage agricole et horticole contenant ledit dérivé et son utilisation - Google Patents

Dérivé de diamide, pesticide à usage agricole et horticole contenant ledit dérivé et son utilisation Download PDF

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Publication number
WO2014178363A1
WO2014178363A1 PCT/JP2014/061824 JP2014061824W WO2014178363A1 WO 2014178363 A1 WO2014178363 A1 WO 2014178363A1 JP 2014061824 W JP2014061824 W JP 2014061824W WO 2014178363 A1 WO2014178363 A1 WO 2014178363A1
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group
alkyl
alkoxy
alkyl group
cycloalkyl
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Japanese (ja)
Inventor
佳典 御所
遠西　正範
三原　純
浩介 深津
大樹 桑原
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • X 1 is (a1) a halogen atom; (a2) (C 1 -C 8 ) alkyl group; (a3) (C 1 -C 8 ) haloalkyl group; (a4) (C 1 -C 8 ) alkoxy group; (a5) (C 1 -C 8 ) haloalkoxy group; (a6) (C 1 -C 8 ) alkylthio group; (a7) (C 1 -C 8 ) haloalkylthio group; (a8) (C 1 -C 8 ) alkylsulfinyl group; (a9) (C 1 -C 8 ) haloalkylsulfinyl group; (a10) (C 1 -C 8 ) alkylsulfonyl group; or (a11) represents a (C 1 -C 8 ) haloalkylsulfonyl group, X
  • R 4 and R 5 are the same as defined above), and (t) aryl having 1-5 substituents on the ring selected from a phenoxy group (C 1 ⁇ C 8) alkyl group; (h14) R 4 (R 5 ) NCO 2 (C 1 -C 8 ) alkyl group (wherein R 4 and R 5 are the same as above) (h15) R 4 (R 5 ) NCO (C 1 -C 8 ) alkyl group wherein R 4 and R 5 are as defined above; or (h16) R 4 (R 5 ) NCO (R 4 ) N (C 1 -C 8 ) An alkyl group (wherein R 4 and R 5 are the same as above).
  • R 3 is (j1) hydrogen atom; (j2) (C 1 -C 8 ) alkyl group; (j3) (C 3 -C 8 ) cycloalkyl group; or (j4) (C 3 -C 8 ) cycloalkyl (C 1 -C 8 ) alkyl; Indicates. ] Or a salt thereof (provided that N 1- ⁇ 2-chloro-4-[(6-heptafluoroisopropyl) -2- (trifluoromethyl) -1H-imidazo [4,5-C except (2-methyl-1- (methylthio) propan-2-yl) phthalamide -] pyridin-1-yl) methyl] phenyl ⁇ -3-iodo -N 2. ).
  • X 1 is (a1) a halogen atom; or (a10) a (C 1 -C 8 ) alkylsulfonyl group, wherein X 2 is (b1) is a hydrogen atom, Y is (c1) hydrogen atom; (c2) a halogen atom; or (c4) a (C 1 -C 8 ) alkyl group, W 2 is, (e12) (C 1 -C 8 ) alkoxy group; or (e14) a (C 1 -C 8 ) haloalkyl group, W 3 is, (f1) hydrogen atom; (f6) (C 1 -C 8 ) alkyl group; (f8) (C 2 -C 8 ) alkynyl group; or (f14) a (C 1 -C 8 ) haloalkyl group, W 4 , W 5 , W 6 , and W 7 may be the
  • Halo means “halogen atom” and represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom
  • (C 1 -C 8 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group , Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, normal hexyl group, isohexyl group, 1,1,2-trimethylpropyl group, 3,3-dimethyl group A linear or branched al
  • (C 2 -C 8 ) alkenyl group means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2- 2 or more linear or branched carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, heptenyl group, octenyl group, etc. Represents 8 alkenyl groups,
  • (C 1 -C 8 ) alkylthio group means, for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group Group, isopentylthio group, tertiary pentylthio group, neopentylthio group, 2,3-dimethylpropylthio group, 1-ethylpropylthio group, 1-methylbutylthio group, normal hexylthio group, isohexylthio group , 1,1,2-trimethylpropylthio group, heptylthio group, octylthio group and the like, which are linear or branched alkylthio groups having 1 to 8 carbon atoms,
  • Examples of the “(C 1 -C 8 ) alkylene group” include methylene group, ethylene group, propylene group, isopropylene group, butylene group and the like.
  • R 1 and R 2 are bonded to each other and contain one nitrogen atom, and further contain 1 to 2 heteroatoms which may be the same or different and are selected from an oxygen atom, a nitrogen atom and a sulfur atom.
  • Preferable 5- to 8-membered nitrogen-containing heterocyclic rings include pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine and the like.
  • Heterocyclic group and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms.
  • Examples of the ⁇ aromatic heterocyclic group '' include, for example, furyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl and the like Cyclic aromatic heterocyclic groups; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, indazolyl, pyrrolopyrazinyl, imidazopyr Aromatic condensed heterocycl
  • non-aromatic heterocyclic group examples include oxiranyl, thiylyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, azolidinyl, oxazolidinyl, oxazolidinyl, Imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-1,3-oxazolidin-5-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1- Dioxide tetrahydropyranyl,
  • heterocyclic group examples include isoquinolinyl, tetrazolyl, quinolinyl, isoxazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrazolyl, benzimidazolyl, 2,3-dioxoisoindolyl, tetrahydrofuranyl, oxiranyl, thienyl, pyridazinyl and the like. It is done.
  • Examples of the salt of the diamide derivative represented by the general formula (I) and the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate and maleate.
  • Organic salts such as acid salts, oxalates, methanesulfonates, benzenesulfonates, paratoluenesulfonates, salts with inorganic or organic bases such as sodium ions, potassium ions, calcium ions, trimethylammonium salts It can be illustrated.
  • X 1 is (a1) a halogen atom; (a6) (C 1 -C 8 ) alkylthio group; (a8) a (C 1 -C 8 ) alkylsulfinyl group; or (a10) a (C 1 -C 8 ) alkylsulfonyl group, wherein X 2 is (b1) is a hydrogen atom, Y is (c1) hydrogen atom; (c2) a halogen atom; (c3) a cyano group; (c4) (C 1 -C 8 ) alkyl group; (c6) (C 1 -C 8 ) alkoxy group; (c8) (C 1 -C 8 ) alky
  • X 1 is (a1) a halogen atom; or (a10) a (C 1 -C 8 ) alkylsulfonyl group, wherein X 2 is (b1) is a hydrogen atom, Y is (c1) hydrogen atom; (c2) a halogen atom; or (c4) a (C 1 -C 8 ) alkyl group, W 2 is, (e12) (C 1 -C 8 ) alkoxy group; or (e14) a (C 1 -C 8 ) haloalkyl group, W 3 is, (f1) hydrogen atom; (f6) (C 1 -C 8 ) alkyl group; (f8) (C 2 -C 8 ) alkynyl group; or (f14) a (C 1 -C 8 ) haloalkyl group
  • X 1 is (a1) a halogen atom; or (a10) a (C 1 -C 8 ) alkylsulfonyl group, wherein X 2 is (b1) is a hydrogen atom, Y is (c1) hydrogen atom; (c2) a halogen atom; or (c4) a (C 1 -C 8 ) alkyl group, W 2 is, (e12) (C 1 -C 8 ) alkoxy group; or (e14) a (C 1 -C 8 ) haloalkyl group, W 3 is, (f1) hydrogen atom; (f6) (C 1 -C 8 ) alkyl group; (f8) (C 2 -C 8 ) alkynyl group; or (f14) a (C 1 -C 8 ) haloalkyl group,
  • the isoimide derivative is reacted with an amine derivative represented by the general formula (3) or the general formula (4) in the presence or absence of an acid or a base in an inert solvent to give a general formula (1-
  • the diamide derivative represented by 1) or (1-2) can be produced, and the diamide derivative represented by the general formula (1-1) or (1-2) is isolated or not isolated.
  • the diamide derivative represented by the general formula (1) can be produced by reacting with the compound represented by the general formula (5) or (6) in an inert solvent in the presence of a base.
  • reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • the target product After completion of the reaction, it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • Aromatic hydrocarbons linear or cyclic ethers such as methyl tertiary butyl ether, diethyl ether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran, esters such as ethyl acetate, amides such as dimethylformamide, dimethylacetamide,
  • An inert solvent such as 1,3-dimethyl-2-imidazolidinone can be exemplified, and these inert solvents can be used alone or in admixture of two or more.
  • Examples of the base used in this reaction include organic bases such as triethylamine and pyridine, inorganic bases such as potassium carbonate, sodium bicarbonate, sodium carbonate and sodium hydroxide, Examples thereof include alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride, alkali metal alcoholates such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide, butyl lithium and the like.
  • the amount used may be appropriately selected from the range of equimolar to excess molar relative to the diamide derivative represented by formula (1-1) or (1-2).
  • reaction temperature can be from room temperature to the reflux temperature of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours.
  • the target product After completion of the reaction, it may be isolated from the reaction system containing the target product according to a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • compounds having a (C 1 -C 8 ) alkylthio (C 1 -C 8 ) alkyl group in the definition of R 1 in the general formulas (1), (1-1) and (1-2) are those skilled in the art. Is usually carried out by oxidation with an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide, so that R 1 is a (C 1 -C 8 ) alkylsulfinyl (C 1 -C 8 ) alkyl group, Alternatively, a compound showing a (C 1 -C 8 ) alkylsulfonyl (C 1 -C 8 ) alkyl group can be produced.
  • an oxidizing agent such as m-chloroperbenzoic acid or hydrogen peroxide
  • the sulfur atom which exists in X ⁇ 1 > can be oxidized similarly, and a sulfinyl body and a sulfonyl body can be manufactured.
  • the amine derivative represented by General formula (4) can be manufactured in accordance with the method described in the international publication 2001-23350 pamphlet, for example.
  • the nitrobenzene derivatives represented by the general formula (3-1) include, for example, a derivative represented by the general formula (3-2) and a derivative represented by the general formula (7) in an inert solvent in the presence of a base.
  • the compound represented by formula (3-1) can be produced by reacting with The inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit the progress of this reaction.
  • chain or cyclic aliphatic hydrocarbons such as pentane, hexane, and cyclohexane
  • Chain or cyclic ethers such as ether, methyl tertiary butyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM);
  • halogens such as methylene chloride, chloroform, carbon tetrachloride Hydrocarbons
  • aromatic hydrocarbons such as benzene, toluene, xylene
  • halogenated aromatic hydrocarbons such as chlorobenzene, fluorobenzene, dichlorobenzene
  • acetone, methyl ethyl ketone (MEK), methyl-i Ketones such as propyl ketone and methyl isobutyl ketone (MIBK)
  • Bases that can be used in this reaction include alkali metal carbonates and bicarbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide.
  • Alkali metal such as alkali metal and alkaline earth metal hydroxide, alkali metal amide such as lithium amide, sodium amide, potassium amide, etc., hydride of alkali metal such as lithium hydride, sodium hydride, potassium hydride, etc.
  • Alkali metal alcoholates such as sodium methoxide, sodium ethoxide, potassium tertiary butoxide, etc., triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA), N, N-dimethylaniline, N, N-diethylaniline, Pyridine, 4-dimethyl Organic bases such as minopyridine (DMAP), 1,4-diazabicyclo [2,2,2] octane (DABCO) and 1,8-diazabicyclo [5,4,0] undec-7-ene (DBU) it can.
  • the amount used can be appropriately selected within the range of 1 molar equivalent to 10 molar equivalents relative to the compound represented by the general formula (3-1).
  • phase transfer catalyst can be used in this reaction, for example, tetramethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide, tetrabutylammonium bissulfate, tetrabutylammonium iodide, trioctylmethylammonium chloride, benzyl Quaternary ions such as triethylammonium bromide, butylpyridinium bromide, heptylpyridinium bromide, benzyltriethylammonium chloride; crown ethers such as dibenzo-18-crown-6, dicyclohexyl-18-crown-6, 18-crown-6 [2.2.2] -cryptate, [2.1.1] -cryptate, [2.2.1] -cryptate, [2.2.
  • each reactant may be used in an equimolar amount.
  • either of the derivatives represented by the general formula (3-2) or the general formula (7) may be used in excess. it can.
  • the reaction temperature can be from room temperature to the boiling point of the inert solvent to be used, and the reaction time is not constant depending on the reaction scale and reaction temperature, but may be in the range of several minutes to 48 hours.
  • After completion of the reaction it may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • nitro-substituted benzoic acids and esters thereof as raw materials for the derivatives represented by the general formula (3-2) are disclosed in Chem. Ber. 52, 1919, 1083; Bull. Soc. Chim. Fr. (1962), 2255-2261; Tetrahedron, (1985), 115-118; Chem. Pharm. Bull. 41, (1993), pages 894-906, etc., and can be produced by a method described in the document or a method analogous thereto.
  • the derivative represented by the general formula (3-1) obtained by the above reaction may be reduced according to the method described in, for example, New Experimental Chemistry Course 14 Oxidation and Reduction [II] (Maruzen Co., Ltd.).
  • an aniline derivative represented by the general formula (3) can be produced.
  • Manufacturing method 3-1 Manufacturing method of Q1 ' (W 2 , W 4 , W 5 , W 6 and W 7 are the same as above.)
  • Derivatives represented by the general formula Q1 ′ are 6-heptafluoroisopropylpyridines prepared from 3,4-diaminopyridine according to the method of JP-A-2001-122636.
  • 3,4-diamine (Qa) was prepared according to J. Am. Am. Chem. Soc. 75, (1953), page 1292, 6-heptafluoroisopropyl-2-trifluoromethyl-1H-imidazo [4,5-C] pyridine can be produced.
  • Manufacturing method 3-2 Manufacturing method of Q3-2 (W 4 , W 5 , W 6 and W 7 are the same as above.)
  • the derivatives represented by the general formula (Q3-2) are those described in (Ja. Heterocycl. Chem. 2, (1965), page 41, 6- (heptafluoroisopropyl) -1H-imidazo [4,5-C] pyridin-2-one can be produced.
  • Manufacturing method 3-3 Manufacturing method of Q3 'and Q4' (Wherein W 3 , W 4 , W 5 , W 6 , W 7 and M are the same as described above, and W represents a protecting group such as an alkoxycarbonyl group.)
  • Derivatives represented by general formula (Q3 ′, Q4 ′) are derivatives represented by general formula (Q4-1, Q3-1) by reacting (Q3-2) with an alkoxycarbonyl halide or the like. 6- (heptafluoroisopropyl) -1H-imidazo [4,5-C] pyridine substituted with W 3 at the 1- or 3-position by subsequent reaction with W 3 M followed by deprotection 2-ones (Q3 ′, Q4 ′) can be produced.
  • Typical examples of the diamide derivative represented by the general formula (I) of the present invention are shown in Tables 1 to 9, 19 and 20, but the present invention is not limited to these. Absent.
  • n- represents normal, iso
  • i- represents iso
  • t- represents tertiary
  • c- represents alicyclic hydrocarbon group
  • Ph represents phenyl group
  • * Indicates enantiomer S form.
  • the physical properties indicate melting point (° C.), refractive index n D (measurement temperature; ° C.) or NMR.
  • Table 18 shows NMR data of a compound described as NMR in the table.
  • the present invention also relates to an aniline derivative or a salt thereof as an intermediate of the diamide derivative of the present invention, and the intermediates are exemplified in Tables 10 to 17.
  • the agricultural and horticultural insecticide containing the diamide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is various agricultural and forestry, horticultural, and stored grains that harm rice plants, fruit trees, vegetables, other crops and florets. It is suitable for pest control such as pests, sanitary pests, and nematodes.
  • Lepidoptera examples include the following: Lepidoptera (Lepidoptera) pests include, for example, Aura moth (Parasa consocia), red killer whale (Anomis mesogona), swallowtail (Papilio xuthus), azukiyamamushiga (Matsumuraeses azukivora), azuki nomeiga (Ostrinia scapulalis), optera a emptera White butterfly (Hyphantria cunea), Common squirrel (Ostrinia furnacalis), Common squirrel (Pseudaletia separata), Common squirrel (Tinea translucens), Common squirrel (Bactra furfurana), Common squirrel (Parnara guttata), Common squirrel Sesamia inferens, Brachmia triannulella, Monema flavescens, Nettle squirrels (Trichoplusia ni), Pleuroptya ruralis, Cystidia
  • Nile white butterfly (Aedia leucomelas), Nashiiraga (Narosoideus flavidorsalis), Nashikenmon (Viminia rumicis), Nashichibiga (Bucculatrix pyrivorella), Nashihisugai (Grapholita molesta), Nashihoso Allium moth (Acrolepiopsis sapporensis), Plodia ⁇ interpunctella, Hellula undalis, Sitotroga cerealella, Spodoptera litura, Species of the genus (Eu) Scopelodes contractus), Orgyia thyellina, Fall army worm (Spodoptera frugiperda), Ostrinia zaguliaevi, Naranga aenescens, Andraca sara nthrene regalis), grape sparrows (Acosmeryx castanea), grape clam (Phyllocnistis toparcha), grape clam (End
  • Euproctis similis corn borer (Acrolepiopsis suzukiella), European corn borer (Ostrinia nubilalis), mung beetle (Mamestra ⁇ brassicae), mugwort (Ascotis ⁇ selenaria), mugwort moths (Odonestis pruni japonensis), apple kenmon (Triaena intermedia), apple cockroach (Adoxophyes orana fasciata), apple coffin (Grapholita inopinata), apple white spider (Spilonota ocellana), apple pilaspatachle (Spilonota ch) Crested Clover (Illiberisunipruni), Argyresthia conjugella, Crimoptera (Caloptilia Maiga (Diaphania indica), fake American tobacco moth (Heliothis virescens), and wateringa (Earias cupreoviridis),
  • insects of the order of the Hemiptera include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, Trigonotylus coelestialium, etc.
  • Oak beetle (Aguriahana quercus), Kasumi beetle (Lygus spp.), Kabawa tofu aphids (Euceraphis punctipennis), citrus scales (Andaspis kashiius), citrus scales (Coccus pseudomagnolia velvet) , Chestnut beetle (Galeatus spinifrons), Chrysanthemum aphid (Macrosiphoniellabornsanborni), Buprestidae (Aonidiella citrina), Hedgehog beetle (Halyomorpha mista), Stephanitis fasciicaza ⁇ L , Cricket lice (Trioza quercicola), walnut grasshopper (Uhlerites latius), grape leaf hopper (Erythroneura comes), black-footed bug (Paromius exiguus), black-footed bug (Duplaspidio) tus claviger, Nephotettix nigropic
  • Aphrophora costalis Japanese cypress (Lygus disponsi), Japanese sword turtle (Lygus saundersi), Japanese pine beetle (Crisicoccus pini), Japanese pine beetle (Empoasca bietis), Matsumoto mori Cic phi , Markopram (Megacopta punctatissimum), Marsyla horn beetle (Eysarcoris guttiger), citrus scale insect (Lepidosaphes beckii), citrus leaf moth (Diaphorina citri), citrus aphid (Toxoptera citricidus), mandarin citri), citrus whitefly (Aleurocanthus spiniferus), citrus leafworm (Pseudococcus citriculus), citrus leafhopper (Zyginella citri), citrus leafhopper (Pulvinaria citricola), mandarin orange Scale insect (Coccus discrepans), citrus scale insect (Pseudaonidia du
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Aohamuri (Eucetonia roelofsi), Azuki weevil (Callosobruchus chinensis), Alci Weevil (Hypera postica), Green weevil (Echinocnemus squameus), Rice beetle (Oulema oryzae), Rice beetle (Oulema orzae) Ladybird (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), weevil (Aulacophora femoralis) Pea weevil (Bruchus pisorum), giant stag beetle (E
  • Diptera (Flyidae) pests include, for example, Culex pipiens pallens, red winged fly flies (Pegomya hyoscyami), red winged fly flies (Liriomyza huidobrensis), house flies (Musca domestica), rice flies Sandy fly (Hydrellia sasakii), Agromyza oryzae, Scarlet flyfly (Hydrellia griseola), Whiteflies (Hydrellia ⁇ ⁇ griseola), Common beetle (Ophiomyia phaseoli), Drosophila cucumber Fly flies such as Rhacochlaena japonica, Muscina stabulans, Megaselia spiracularis, Clogmia albipunctata, Tipula alex niorhynchus), Anopheles sinensis, radish fly (Hylemya brassicae), soybean fly
  • Hymenoptera pests (Pristomyrmex ponnes), Arachibachie, Moneorumium pharaohnis, Pheidole noda, Athalia rosae, Cristodon (Dryocosmus kurius), japonica), hornets, sedge bee (Athalia infumata), horned bee (Arge pagana), Japanese bee (Athalia japonica), hachiriari (Acromyrmex spp.), fire ant (Solenopsis spp.), apple bee (Arge pa) Ruriari (Ochetellus glaber),
  • insects of the order Diptera include, butterfly (Homorocoryphus lineosus), kerat (Gryllotalpa sp.), Coago (Oxya hyla intricata), Cobainago (Oxya yezoensis), Tosama locust (Locusta migraya), Oneya ⁇ p Himeksakiri (Homorocoryphus jezoensis), and Emma cricket (Teleogryllus emma),
  • thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Thrips thrips (Haplothrips aculeatus), Thrips thrips, obscurus), black thrips (Lisrips floridensis), gladiolus thrips (Thrips simplex), black thrips (Thrips nigropilosus), black thrips (Heliothrips haemorrhoidalis), blue thrips Thrips (Leeuwenia pasanii), Shiimaruda thrips (Litotetothrips pasaniae), Citrus srips (Scirtothrips citri), Thrips thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines) Thrips Thrips hawaiiensis, Haplothrips kurdjumovi,
  • Examples of the pests of the mite include: Leptotrombidium akamushi, American dock chick (Dermacentor variabilis), house dust mite (Ornithonyssus bacoti), black mite (Demodex canis), mite (Rhipicephalus sanguineus) Tetranychus ludeni, Tetranychus truncatus, Mite spider mite (Tetranychus viennensis), Kanzawa spider mite (Tetranychus kanzawai), Stag beetle mite (Cheyletus malaccensis), Spider mite (Tyrophae Dermacentor taiwanicus, Acaphylla ⁇ theavagrans, Dust mite (Polyphagotarsonemus latus), Tomato ticks (Aculops lycopersici), Tosa mite (Ornithonyssus sylvairum), Nite spider mite (Tetranychu urticae), Scarlet mite
  • molluscs examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Icustabdespect .
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • tick mite Haemaphysalis kitaokai
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • tick Haemaphysalis kitaokai
  • Of tick Ixodes persulcatus
  • kingfisher tick Amblyomma testudinarium
  • giant tick Haemaphysalis megaspinosa
  • amino tick Dermacentor reticulatus
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • the animal parasite control agent containing the compound of the present invention is particularly effective for controlling fleas belonging to the family Flea, particularly dog fleas and cat fleas.
  • the animal parasite control agent of the present invention is also effective against endoparasites, and examples of such endoparasites include lungworms, venthus, tuberous worms, stomach parasites, roundworms, and filamentous worms.
  • endoparasites include lungworms, venthus, tuberous worms, stomach parasites, roundworms, and filamentous worms.
  • Nematodes, crustaceans such as Manson's crested worm, caudate cutworm, crustacea, multi-headed crustacea, single-banded crested worm, and multi-banded crested worm, schistosoma japonicum, and liver Insects such as moths, and protozoa such as coccidium, malaria parasites, intestinal granulocysts, toxoplasma, and cryptosporidium are included.
  • the agricultural and horticultural insecticide containing the diamide derivative represented by the general formula (I) of the present invention as an active ingredient is used for the above-mentioned pests that cause damage to paddy field crops, field crops, fruit trees, vegetables, other crops, flowers, etc. It has a remarkable control effect, so that it is possible to raise seedlings, paddy fields, fields, fruit trees, vegetables, other crops, flower buds, etc. before or when the occurrence of pests is confirmed, according to the time when the occurrence of pests is expected.
  • the desired effect of the agricultural and horticultural insecticide of the present invention can be obtained by treating the seeds, paddy water, stalks and leaves, or soil and other cultivation carriers.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited. Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomatoes, spinach, broccoli, lettuce, onions, green onions, peppers, eggplants, strawberries, peppers, porridges, etc.), root vegetables (carrots, potatoes, sweet potatoes, sweet potatoes, daikon, turnips, lotus roots, burdock, garlics, etc.), crops for processing ( ⁇ , hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc.), cucumbers (pumpkin, cucumber, watermelon, (Wow, melon, etc.), pastures (orchard grass, sorghum, timothy, clover, alfalfa
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazetapyr and thifensulfuron methyl
  • EPSP synthase inhibitors such as glyphosate
  • glutamine synthase inhibitors such as glufosinate, cetoxydim and the like.
  • plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to resistance to herbicides such as
  • Plants to which tolerance to an acetyl-CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance into a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, etc.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination with these techniques or systematized.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • they can also be used for application to house building materials, smoke, baits, and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings are used for cultivation. Mention may be made of plants for vegetative propagation.
  • the dosage form may vary depending on the time of application such as application at seeding, greening period, application at transplanting, etc., but agents such as powder, granule wettable powder, granules, etc. Apply by mold. It can also be applied by mixing with cultivating soil, and it can be mixed with cultivating soil and powder, granulated wettable powder or granules, for example, mixed with floor soil, mixed with covering soil, mixed into the entire cultivated soil and the like. Simply, the soil and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, pack agents, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate formulation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • the plant source of the plant being cultivated In field crops, it can be treated to seeds or a cultivation carrier close to the plant body from sowing to raising seedling.
  • treatment on the plant source of the plant being cultivated is suitable.
  • a spray treatment using a granule or a irrigation treatment in a liquid of a drug diluted or not diluted with water can be performed. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the granule spraying treatment to the seedling nursery is preferred.
  • the solid support examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • Cationic surfactants such as alkylamine salts such as laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylaminopropylamine acetate, alkyltrimethylammonium chloride, alkyldimethylbenzalkonium chloride,
  • amphoteric surfactants such as amino acid type or betaine type. These surfactants may be used alone or in combination of two or more.
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
  • the amount of the pest control agent of the present invention is various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application Depending on the location, application time, etc., the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg per 10 ares according to the purpose.
  • the pesticides of the present invention can be further controlled against other pests, insecticides for agro-horticultural use, acaricides, It can be used by mixing with nematodes, fungicides, biological pesticides, etc., and it can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc. depending on the situation of use.
  • Other agricultural and horticultural insecticides, acaricides, nematicides used for such purposes include, for example:
  • XMC 3,5-xylyl methylcarbamate
  • Bacillus thuringienses aizawai Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, azinphos-methyl, acequinocyl, acetamiprid,
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (EntomopoXI virus, EPV) ) Virus preparations, Monocrosporium ⁇ ⁇ phymatophagum, Steinernema ⁇ carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Sterilization of microbial pesticides, Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
  • microbial pesticide to be used by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • examples of biological pesticides include Encarsia ⁇ ⁇ formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysilis (Dacnusahysticulus) ), Natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1- Can be used in combination with pheromone such as octadecene It is.
  • Reference Example 1-1 Preparation of 1.6-heptafluoroisopropylpyridine-3,4-diamine and 2-heptafluoroisopropylpyridine-3,4-diamine 5.0 g of 3,4-diaminopyridine is added to a mixed solvent of 46 mL of ethyl acetate and 46 mL of water, 16.3 g of heptafluoro-2-iodopropane, 14.6 g of sodium carbonate, and 1.0 g of tetrabutylammonium hydrogen sulfate. Were added sequentially. The mixture was stirred in a 50 ° C.
  • Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Test Example 2 Insecticidal test against green planthopper ( Nilaparvata lugens ) Disperse the compounds listed in Tables 1 to 5 in water and dilute in 500ppm chemical solution, soak rice seedlings (variety: Nipponbare) in the chemical solution for 30 seconds and air-dry Later put into a glass test tube, inoculate 10 each of the 3 planted brown planters, and then plug the cotton plug. After 8 days of inoculation, the number of live and dead insects was investigated, and the corrected death rate was calculated from the following formula. The determination was performed according to the determination criteria described in the section.
  • Test Example 3 Control test against peach aphid ( Myzus persicae ) Chinese cabbage aphid larvae were inoculated by planting Chinese cabbage in a plastic pot having a diameter of 8 cm and a height of 8 cm. The next day, a drug (500 ppm) containing the compound shown in Tables 1 to 5 as an active ingredient is sprayed on the stems and leaves of potted Chinese cabbage, air-dried, and the pot is stored in a greenhouse. The number of parasites of peach aphid infesting each Chinese cabbage was investigated, the control value was calculated from the following formula, and the determination was made according to the following criteria.
  • Ta Number of parasites before spraying in the treated zone
  • Ca Number of parasites before spraying in the untreated zone
  • C Criteria for determining the number of parasites after spraying in the untreated zone.
  • Test Example 4 Insecticidal test against Plutella xylostella Sponge seedlings are allowed to lay eggs and lay eggs, and two days after the release, cypress seedlings with spawning eggs are treated with the compounds listed in Tables 1 to 5 as active ingredients.
  • Six days after immersion in the chemical solution the number of hatching insects was investigated, the death rate was calculated according to the following formula, and the determination was made according to the following criteria. 1 ward, 10 heads, 3 systems.

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Abstract

Dérivé de diamide représenté par la formule générale (I), et sel ou analogue de celui-ci. (Dans la formule, X1 représente un atome d'halogène ou analogue ; X2 représente un atome d'hydrogène ou analogue ; Y représente un atome d'hydrogène, un atome d'halogène, un groupe alkyle ou analogue ; Z1, Z2 et Z3 peuvent être identiques ou différents les uns des autres et représentent chacun un atome d'azote, CH, C-Y1 ou C-A-Q (au moins l'un de Z1, Z2 et Z3 représentant C-A-Q) ; A représente un groupe alkylène en C1-C8 linéaire ou ramifié ; Q représente un groupe hétérocyclique condensé spécifique ; R1 représente un groupe C1-C8 alkylthio C1-C8 alkyle ou analogue ; chaque R2 et R3représente un atome d'hydrogène ou analogue ; et Ar représente un groupe cycle aryle spécifique.)
PCT/JP2014/061824 2013-04-30 2014-04-28 Dérivé de diamide, pesticide à usage agricole et horticole contenant ledit dérivé et son utilisation Ceased WO2014178363A1 (fr)

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