WO2006137389A1 - Nouvel agent insecticide/miticide - Google Patents

Nouvel agent insecticide/miticide Download PDF

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Publication number
WO2006137389A1
WO2006137389A1 PCT/JP2006/312305 JP2006312305W WO2006137389A1 WO 2006137389 A1 WO2006137389 A1 WO 2006137389A1 JP 2006312305 W JP2006312305 W JP 2006312305W WO 2006137389 A1 WO2006137389 A1 WO 2006137389A1
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Prior art keywords
group
halogen atom
substituted
alkyl
atom
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PCT/JP2006/312305
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English (en)
Japanese (ja)
Inventor
Kimihiko Goto
Nozomu Nakanishi
Ryo Horikoshi
Mariko Tsuchida
Kazuhiko Oyama
Kazumi Yamamoto
Masahiro Nomura
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Meiji Seika Kaisha Ltd.
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Priority to JP2007522288A priority Critical patent/JP4970255B2/ja
Publication of WO2006137389A1 publication Critical patent/WO2006137389A1/fr

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    • 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
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel insecticidal and acaricidal composition.
  • the nicotinic acid-lide derivative has an insecticidal and acaricidal activity!
  • the substituent structure on the aryl is different from the compounds of the present invention.
  • WO2002066470, WO2001023347, WO2001014339, WO2001005769, W0992 4404, DE19629828 do not disclose similar nicotinic acid-lide derivatives. There is no description about.
  • Patent Document 1 US2004 / 0249164
  • Patent Document 2 JP-A-6-321903
  • Patent Document 3 WO2002096882
  • Patent Document 4 WO2002066470
  • Patent Document 5 WO2001023347
  • Patent Document 6 WO2001014339
  • Patent Document 7 WO2001005769
  • Patent Document 8 WO9924404
  • Patent Document 9 DE19629828
  • An object of the present invention is to provide a derivative having excellent insecticidal and acaricidal activity, and to further induce the derivative.
  • An effect of containing a conductor is to provide an insecticidal and acaricidal composition that can be used safely and safely.
  • the first present invention provides an insecticidal and acaricidal composition
  • R is a hydrogen atom, a hydroxyl group, a halogen atom, or a halogen atom.
  • R 1 1 represents an alkyl group or a C alkoxy group optionally substituted with a halogen atom
  • ⁇ 6 1 ⁇ 6 2 are hydrogen atom, halogen atom, OR, OC OR, NR, R,, SR, SC OR, (R, R,
  • 2 2 2 2 2 2 2 2 2 2 2 2 2 2 are the same or different and are a hydrogen atom, a halogen atom, a C alkoxy group, or
  • R or R are the same or different and are a hydrogen atom, a hydroxyl group, a halogen atom, or a halogen atom.
  • Bonyl group C alkylcarbonyloxy group, halogen atom or C alkoxy
  • R and R together can form a 5-7 membered saturated cyclic alkyl or saturated heterocycle Yogu
  • R represents a hydrogen atom or a C alkyl group
  • W represents a group —Y—W
  • W ′ represents an optionally substituted phenyl group (wherein the substituent is a halogen atom, substituted with a halogen atom, a C alkyl group, Halogen atom
  • a C alkoxy group optionally substituted with a mono- or di-C alkyl-substituted amino group
  • the two groups formed together may be substituted with a halogen atom—0— (CH 2) —0— (where p represents 1 or 2) or substituted May be saturated
  • Y is (CH), 0 (CH), S (CH) (CH) 0, (CH)
  • X may be substituted with a hydroxyl group, a halogen atom, or a halogen atom;
  • 1 to 6 1 to 6 represents a carboxy group or a C alkyl carboxy group
  • n an integer of 0 to 4
  • n an integer of 0 to 4, provided that
  • R to R or R, R and R do not all represent the same hydrogen atom.
  • the second present invention provides a compound represented by the following formula (A) or an agriculturally and horticulturally acceptable acid addition salt thereof.
  • R represents a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group
  • R is OR, or ⁇ C ⁇ R, (R is the same or different and is a hydrogen atom or halo.
  • Yo ! represents a C alkyl group
  • Y is (CH), 0 (CH), S (CH) (CH) 0, (CH) S, NR (CH) or (CH) NR (R is
  • 2 1 2 1 2 1, 2 1 2 1 y 2 1 2 1 y y represents a hydrogen atom, C alkyl group), 1 represents an integer of 0-4,
  • w and w may be the same or different and may be substituted with a halogen atom or a halogen atom.
  • 1 to 6 101 102 may be substituted with a halogen atom formed together and two groups are joined together —0— (CH 2) —0— (where p represents 1 or 2) )
  • W is hydrogen atom, halogen atom, C alkyl optionally substituted by halogen atom.
  • 1 to 6 1 represents an alkyloxycarboxyl group or a C alkylcarboxyl group
  • X is a hydroxyl group, a halogen atom, a halogen atom substituted, a C alkyl group,
  • C alkoxy group optionally substituted with halogen atoms, mono or di C alkyl Substituted with a substituted amino group, cyano group, nitro group or halogen atom, C alkyl
  • 1 to 6 1 to 6 represents a carboxy group or a C alkyl carboxy group
  • n an integer of 0 to 4.
  • the compound of the present invention exhibits an excellent control effect against harmful insects and mites, and is useful as a novel insecticide and acaricide.
  • no, rogen means fluorine, chlorine, bromine and iodine
  • the halogen atom in formula (1) is preferably a fluorine atom or a chlorine atom.
  • alkyl group is a saturated or unsaturated linear or branched C alkyl group.
  • R is preferably a hydrogen atom, a hydroxyl group, a halogen atom, C alkyl
  • R is preferably a hydrogen atom, a hydroxyl group, a halogen atom, a C alkoxy group, a C alkyl group.
  • Group more preferably a hydroxyl group or a C 4 alkylcarbonyloxy group.
  • R may also represent! Hydrogen groups on the “phenol group” and “phenol group”
  • Substituents that may be substituted include halogen atoms, C alkoxy groups that may be substituted with halogens, C alkyl groups that may be substituted with halogens, halogens.
  • R is preferably a hydrogen atom, a hydroxyl group, a C alkoxy group, a full group, or a fullyl group.
  • R is preferably a hydrogen atom, a hydroxyl group, a C alkoxy group, a phenyl group, a phenyl group.
  • R is preferably a hydrogen atom.
  • the saturated or unsaturated 5- or 6-membered heterocyclic ring represented by W is the same or different, and is a heterocyclic ring having 1 to 4 heteroatoms selected from the group force of nitrogen, oxygen and sulfur.
  • Specific examples include chenyl group, furyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, isothiazolyl group, isoxazolyl group, thiazolyl group, oxazolyl group, pyridyl group, pyrimidyl group, birazinyl group, pyridazinyl group.
  • a pyridyl group Preferably a pyridyl group.
  • the heterocyclic ring may be substituted with a halogen atom, C alkyl
  • Examples thereof include a fluoromethoxy group, a trifluoromethylthio group, a trifluoromethylsulfyl group, a trifluoromethylsulfol group, a acetyl group and an acetyloxy group, and a halogen atom is preferred.
  • W is preferably W, force A phenyl group which may be substituted (wherein the substituent may be substituted with a halogen atom or a halogen atom, or may be substituted with a C alkyl group or a halogen atom)
  • Two adjacent groups formed together, substituted with a halogen atom, may be 0— (CH 2) —0 (where p is 1 or 2) or substituted May be
  • a pyridyl group (wherein the substituent is a halogen atom), and ⁇ is a bond, an oxygen atom, a sulfur atom, or a group —Y—W, which is —OCH—, more preferably a substituted Yo
  • phenoxy group (substituent is a halogen atom, substituted with a halogen atom !, may be! / ⁇ C alkyl group, C alkoxy group optionally substituted with a halogen atom, cyano group, Substituted with a halogen atom, it may be substituted with a C alkylthio group or a halogen atom.
  • halogen atom which may be-0-(CH) -0- (where p is 1 or 2)
  • p is 1 or 2
  • phenyl group Benzyloxy group or
  • a phenylthio group which may be substituted (the substituent is a halogen atom or a C alkyl group which may be substituted with a halogen atom).
  • X is preferably a halogen atom or a C alkyl optionally substituted with a halogen atom.
  • n is preferably an integer of 0 or 1.
  • m is preferably an integer of 0 or 1.
  • R is preferably a hydrogen atom, a chlorine atom or a methyl group.
  • R is preferably a hydroxyl group or OCOR, (R represents a C alkyl group).
  • Y is preferably a bond, an oxygen atom or a sulfur atom.
  • w and w are preferably the same or different and are substituted with a halogen atom or a halogen atom.
  • W is preferably a hydrogen atom.
  • X is preferably a halogen atom, substituted with a halogen atom, or C alkyl
  • n is preferably an integer of 0 or 1.
  • R 1S hydrogen atom, hydroxyl group, halogen atom, C
  • 1 represents a 1-6 alkyl group or a C alkoxy group
  • R represents a hydrogen atom
  • W is an optionally substituted phenyl group (wherein the substituent is a halogen atom, substituted with a halogen atom, a C alkyl group, Halogen field
  • a C alkylsulfier group optionally substituted with
  • a pyridyl group (wherein the substituent is a halogen atom), ⁇ represents a bond, an oxygen atom, a sulfur atom or OCH;
  • 1-6 represents an alkoxy group
  • n an integer of 0 or 1
  • m force represents an integer of 0 or 1.
  • R force hydrogen atom, C alkyl group or
  • R force represents a hydroxyl group or a C alkylcarbonyloxy group
  • R and R force C represents an alkoxy group
  • R represents a hydrogen atom
  • W force An optionally substituted phenyl group (the substituent may be substituted with a halogen atom or a halogen atom, or a C alkyl group or a halogen atom may be substituted with a C atom.
  • Or may be substituted with a halogen atom formed by joining two adjacent groups on a phenyl group together — 0— (CH 2) —0— (where p is 1 or 2 Yes))
  • n an integer of 0 or 1
  • m force represents an integer of 0 or 1.
  • R force is a hydrogen atom, a chlorine atom or a methyl group
  • R force hydroxyl group or OC OR, (R represents a C alkyl group)
  • Y is a bond, an oxygen atom or a sulfur atom
  • w and W forces are the same or different and are substituted with halogen atoms or halogen atoms
  • 6 1-6 101 and W are substituted by a halogen atom, formed by two adjacent groups and two groups together.
  • a compound in which m is an integer of 0 or 1 or an agriculturally and horticulturally acceptable acid addition salt thereof is provided.
  • an insecticidal and acaricidal composition comprising a compound of formula (A) or an agriculturally and horticulturally acceptable acid addition salt as an active ingredient.
  • the agriculturally and horticulturally acceptable acid addition salt of the compound represented by the formula (1) or the formula (A) of the present invention includes, for example, hydrochloride, nitrate, sulfate, phosphate, acetate. Etc.
  • the compound of the present invention represented by the formula (la) can be produced by the method shown in the following scheme 1.
  • R, R, R, R, X, W, m, n force are as described in the formula (1), Z force S hydroxyl group,
  • H is an alkyloxy group.
  • it can be produced by condensing the substituted nicotinic acid derivative (2) and the arylene or phenol alkylamine (3). Further, if necessary, it can also be produced by converting W, X of the compound (la) after condensation into another appropriate substituent.
  • acid halogen compound generators such as phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride and thiol chloride, mixed acid anhydrides such as ethyl chloroformate and methanesulfonyl chloride
  • Product generator ⁇ , ⁇ '-Dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (WSCI-HC1), ⁇ , ⁇ -Carposi Examples include imidazole, 2-ethoxy-N-ethoxycarbo-l, 2-dihydroquinoline (EEDQ), triphenylphosphine-tetrasalt-carbon (complex), and the like.
  • active esterifying agents such as 1-hydroxybenzotriazole (HOBt) or 1-hydroxy-7-azabenzotriazole (HOAt), N-hydroxy succinimide, acid supplements such as N —
  • the compound of formula (la) can be synthesized by reacting with a condensing agent in the presence of methylmorpholine (NMM), triethylamine, 4- (dimethylamino) pyridine (DMAP) or diisopropylethylamine.
  • Solvents include aromatic hydrocarbons such as benzene, toluene and xylene, halogenated aromatic hydrocarbons such as black benzene and dichlorobenzene, aliphatic hydrocarbons such as hexane, cyclohexane and petroleum ether, Aliphatic halogens such as dichloromethane, 1,2-chloroethane, chloroform, tetrasalt and carbon, ethers such as jetyl ether, diisopropyl ether, dioxane and tetrahydrofuran, ketones such as acetone and 2-butanone , Acetonitrile, -tolyl such as propiol-tolyl, amides such as ⁇ , ⁇ - dimethylformamide, hexamethylphosphoric triamide ( ⁇ ), sulfoxides such as dimethyl sulfoxide or a mixed solvent thereof Etc.
  • aromatic hydrocarbons such as benzene, toluene and
  • the compound represented by the formula (lb) is obtained by reacting the compound of the formula (la) with an alkyl halide in the presence of a base group or in the absence of a base, and if necessary It can be synthesized by converting a substituent.
  • R force is a C-anolequinol group
  • R, R, R, R, X, W, m, n force as described in the formula (1)
  • Examples of the base include organic amines such as triethylamine and pyridine, and inorganic alkalis such as potassium carbonate, sodium carbonate, and sodium hydride.
  • the compound of the formula (lc) has R in the formula (1) as OH.
  • the compound of the formula (1 ′) can also be synthesized by reacting with an alkylating agent or an acylating agent in the presence or absence of a base.
  • R is OR, OC OR, where R is as described in formula (1), R, R, R,
  • R, X, W, m, and n are as described in the formula (1).
  • alkylating agent to be used examples include alkyl halides, diazomethane, dimethyl sulfate, and dimethyl sulfate.
  • acylating agent examples include carboxylic acid, acid anhydride, and halogenated acyl.
  • the base examples include organic amines such as triethylamine and pyridine, and inorganic alkalis such as potassium carbonate, sodium carbonate and sodium hydride.
  • the compound represented by the formula (2) can be produced by the method shown in the following scheme 4.
  • R, R, R, R force are as described in formula (1), and Z is a hydroxyl group or a lower alkyl group.
  • Q is a methyl group, a halogenated methyl group, a hydro gen in formula (5a) Xylmethyl group, lower alkoxymethyl group, formyl group, cyano group, tertiary aminomethyl group, propargyl group, acid hydrazide.
  • formula (5b) cyano group, nitro group, ester group, 1, 1, 1-trihalogen Methyl group, acid halide, acid anhydride, acid amide, acid imide, acid hydrazide and aldoxime.
  • a substituted pyridyl derivative (4) obtained by converting a substituent by a commercially available or standard procedure is converted into a methyl group, a halogenated methyl group, a hydroxymethyl group, a lower alkoxymethyl group in the presence or absence of a base.
  • a compound represented by formula (2) can be synthesized by synthesizing a derivative (5a) into which a group, formyl group, cyano group, tertiary aminomethyl group, propargyl group, or acid hydrazide is introduced, and then carrying out an oxidation reaction. it can.
  • a methyl group, a halogenated methyl group, a methyl alcohol group, a formyl group, or a cyan group is used.
  • the compound represented by the formula (2) can be obtained by reacting the compound (4) with or without a base, a cyan group, a -together group, an ester group, a 1,1,1 trihalogenated methyl group, an acid halide, It can also be synthesized by synthesizing a derivative (5b) into which an acid anhydride, acid amide, acid imide, acid hydrazide or aldoxime has been introduced, followed by a hydrolysis reaction.
  • a cyan group or an ester group is used.
  • the compound of formula (2) can also be synthesized by reacting compound (4) with carbon monoxide, carbon dioxide or formic acid in the presence of a base.
  • the methylating agent used include methyl halide, dimethyl sulfate, and diazomethane.
  • the hydroxymethylating agent include formaldehyde and paraformaldehyde.
  • Halogenated methylating agents include 1, 1-dibromomethane, 1-bromo 1-chloromethane, and 1, 1-dichloromethane.
  • the formylating agent include 1,1-dimethylformamide, methyl formate, and ethyl formate.
  • cyanating agents include metal cyanides such as cyanogen potassium, cyanium sodium and copper cyanide, cyanogen bromide, and toluene cyanide cyanide.
  • esterifying agent include carbon monoxide, carbon dioxide, and halogenated alkyl carbonate.
  • the compound represented by the formula (3) can be produced by the method shown in the following scheme 5.
  • the compound of formula (6a) which is W 0-W 'in formula (6) can also produce the compound of formula (7) and compound power of formula (8). it can.
  • a compound of formula (6a) can be synthesized by reacting a generally available -tro compound of formula (7) and an alcohol of formula (8) in the presence of a base or in the absence of a base.
  • Hal represents a halogen atom such as fluorine, chlorine, bromine or iodine.
  • the derivative represented by the formula (A) of the present invention can also be synthesized by the same method as that for the compound of the formula (1).
  • insect species in which the derivative represented by the formula (1) or the formula (A) of the present invention exhibits a controlling effect include: Lepidopterous pests such as Spodoptera, Rhinoceros, Adonto, Aomushi, Konaga, Ichimojoto, Nikameiga, Shironogaiga, Tokigaiga, Shintaiga, Hamoguriga, Dokuga, Tobacco, etc. Aphids, corn aphids, stag beetles, tiger moth powers, white-spotted grasshoppers, stink bugs, whitefly worms, bugs, etc.
  • Lepidopterous pests such as Spodoptera, Rhinoceros, Adonto, Aomushi, Konaga, Ichimojoto, Nikameiga, Shironogaiga, Tokigaiga, Shintaiga, Hamoguriga, Dokuga, Tobacco, etc.
  • Aphids corn aphids, stag beetles, tiger moth powers, white-spotted
  • Doganebuibu Doganebuibu, hime-kogane, kissing flea beetle, cucumber potato beetle, colorado potato beetle, rice beetle bug, stag beetle, beetle, etc., Acarina, for example, namihada-, senami Mites, mandarin mites, mandarin mites, apple mites, citrus scabs, chianosabidani, pears, etc., hymenoptera, for example, wasps, ostracods, for example grasshoppers, diptera, for example, houseflies, leafhoppers, thrips Pests such as the southern mouth of the moss, Thrips thrips, and parasitic nematodes of the plant, such as Nekobu Sentiyu, Nesare Sentiyu, Inesinga Sentiyu, Matsunoza Sentiyu, etc. Excellent
  • a compound represented by the formula (A) or an agriculturally and horticulturally acceptable acid addition for producing an agricultural and horticultural insecticidal or acaricidal composition The use of salt is provided. Such use can be easily carried out based on the contents described above.
  • the derivative may be used as it is, but is usually suitable.
  • Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, quartz sand, quartzite, zeolite, pearlite, attapulgite, pumice, ammonium sulfate. And sodium sulfate and urea.
  • liquid carrier examples include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol and propylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, n-hexane, Aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as toluene, xylene and methylnaphthalene, ethers such as jetyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, acetononitrile and isobutyryl Examples include -tolyls such as mouth-tolyl, acid amides such as dimethylformamide and dimethylacetamide, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, and water.
  • alcohols such as methanol, ethanol, n-hexanol, ethylene glycol and propylene glyco
  • gaseous carrier examples include LPG, air, nitrogen, carbon dioxide, dimethyl ether, and the like.
  • Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohols. Esters, lignosulfonates, alkylsulfosuccinates, formalin condensates of alkylnaphthalenesulfonates, polycarboxylates, POE polystyryl vinyl ether sulfates and phosphates, POE'POP block polymers, etc. are used.
  • adjuvants for improving the properties of the preparation include, for example, carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, hi starch, gum arabic, polyethylene glycol, liquid paraffin, calcium stearate. Dehumidifiers, antifoaming agents, preservatives and the like are used.
  • the content of the active ingredient in these preparations is usually 175% by weight for emulsions, usually 0.3-25% by weight for powders, usually 1-90% by weight for wettable powders, and usually 0. 5-10% by weight Is appropriate.
  • These preparations are used as they are or after being diluted. These preparations can also be used by mixing with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.
  • Examples of drugs that can be used in combination include the Pesticide Manual (13th edition The
  • insecticides, acaricides or nematicides used include, for example, acephate, dichlorvos, EPN, fenitrothion, fenamifos, prothiofos, prothiofos, (profenofos), pyraclofos (py raclofos), chlorpyrifos-methyl (chlorpyrifos-methyl), organophosphate compounds such as diazinon, mesomyl (methomyl), thiodicarb, thiodicarb, aldicarb, oxaminole ( oxamyl), propoxurole (propoxur), force noreno linole (carbaryl), fenobucarb (fenobucarb), ethiofencarb (ethiof)
  • Uran benfuranocarb Carbamate compounds such as cartap
  • Nereistoxin derivatives such as thiocyclam
  • organochlorine compounds such as dicofol, tetradifon, permethrin, tefluthrin, cypermethrin, tenoletamethrin (deltamethrin)
  • Pyrethroid compounds such as cyhalothrin, fenvalerate, fluvalerate, etofenprox, silafluofen, diflubenzuron, teflubenslon
  • Benzoylurea compounds such as teflubenzuron, flufenoxuron, chlorfluazuron, juvenile hormone-like compounds such as metoprene, and other compounds such as buprofezin, hexithiazox ( hexythiazox), Ami Amitraz, chlordimeform, pyridaben, fenpyroxymate, pyr
  • fungicides to be used include streptvillin-based compounds such as azoxystrobin, kresoxym-methyl, trifloxystrobin, and mepanipyrim. ), Pyrimethanil, cyprodinil-like alinopyrimidine compounds, triadimefon, bitertanol, triflumizole, etaconazonole (etaconazole) ), Propiconane ⁇ Nore (propiconazole), Henconane ⁇ Nore (penconazole), Funolenfuzo ⁇ Nore (flusilazole no), Microbutaninole (myclobutanil), Cyproconazononorre (cyproconazole), Tebuconazonole (te buconazole), Hexaconazole hexanoazole, prochloraz ⁇ simeconazo simeconazole Quinoxaline compounds such as quinomethionate, dithiocarbamate,
  • an effective amount of the compound represented by the formula (1) or an agriculturally and horticulturally acceptable acid addition salt thereof is applied to various application targets, particularly plants or soils.
  • a method for controlling agricultural and horticultural pests, in particular mites comprising applying to. Therefore, when carrying out the control method according to the present invention, at least an effective amount of the compound represented by the formula (1) or an acid-addition salt acceptable in agriculture and horticulture should be applied to various applications.
  • One or more known pre-treatments or post-treatments used for the control of other agricultural and horticultural pests may be included.
  • the compound represented by the formula (1) or an acid addition salt acceptable in agriculture and horticulture is as described above.
  • the effective amount of the compound represented by the formula (1) described above or an acid-addition salt acceptable in agriculture and horticulture is not particularly limited, but preferably 1 to 75 when an emulsion is selected as the dosage form.
  • % By weight, preferably 0.3 to 25% by weight when powder is selected, preferably 1 to 90% by weight when wettable powder is selected, preferably 0.5 to when granular is selected: L0 Weight%.
  • an effective amount of the compound represented by the formula (A) or an agriculturally and horticulturally acceptable acid addition salt thereof is applied to various applications, particularly plants or soils.
  • a method for controlling agricultural and horticultural pests, especially mites comprising: Therefore, at the time of carrying out the control method according to the present invention, at least an effective amount of the compound represented by the formula (A) or an acid addition salt acceptable in agriculture and horticulture should be applied to various applications.
  • One or more known pre-treatments or post-treatments used for the control of other agricultural and horticultural pests may be included.
  • the compound represented by the formula (A) or the acid addition salt acceptable in agriculture and horticulture is as described above.
  • the effective amount of the compound represented by the above-mentioned formula (A) or an acid and pharmaceutically acceptable acid addition salt thereof is not particularly limited, but preferably 1 to 75 when an emulsion is selected as the dosage form.
  • % When powder is selected preferably 0.3 to 25% by weight, preferably 1 to 90% by weight when wettable powder is selected, preferably 0.5 to 10 when granule is selected % By weight.
  • the compound represented by the formula (1), the compound represented by the formula (A), or an acid-addition salt acceptable in agriculture and horticulture is applied. It also includes applying by a known or later-developed processing method such as applying by smoke treatment in a sealed space.
  • reaction solution was charged with 8 ml of a solution of acetic acid ZEtOHZTHF (2 Z2Z4) and then brought to room temperature and 20 ml of a saturated aqueous potassium carbonate solution.
  • Tetrahydrofuran was distilled off under reduced pressure, followed by extraction with ethyl acetate.
  • the organic layer was dehydrated with anhydrous sodium sulfate, and then the solvent was distilled off. Purification on a silica gel column (hexane Z ethyl acetate: 8/1) gave 6-methyl-2,3-dimethoxy-4-pyridyl N, N-diisopropylcarbamate.
  • the reaction mixture was filtered to remove the catalyst, and the solvent was distilled off under reduced pressure to obtain 2- [4- (trifluoromethyl) phenoxy] aline (274 mg).
  • 3,5-Bis (trifluoromethyl) thiophenol (1.2 g) was obtained in a dimethylformamide solution (5 ml) of 60% sodium hydride (0.2 g) under ice cooling. After stirring at room temperature for 1 hour, 2-promonitrobenzene (0.5 g) was added and heated to reflux. After 21 hours, the mixture was cooled at room temperature, immersed in water, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure.
  • a saturated aqueous sodium hydrogen carbonate solution was prepared and extracted with ethyl acetate, and the organic layer was washed with a 1 mol ZL aqueous solution of taoic acid and a saturated aqueous sodium chloride solution.
  • Organic layer with anhydrous sodium sulfate After dehydration and evaporation of the solvent, purification by preparative TLC gave 4.8 mg of compound 2.
  • a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate.
  • the organic layer was washed with 1 mol ZL of aqueous citrate and saturated aqueous sodium chloride.
  • the organic layer was dehydrated with anhydrous sodium sulfate, and the solvent was distilled off.
  • a tetrahydrofuran solution in which 59 mg of 2- (4-tertbutylbutylphenoxy) -line was dissolved was prepared and stirred at room temperature for 3 hours.
  • a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate.
  • the organic layer was washed with 1 mol ZL of aqueous citrate and saturated aqueous sodium chloride.
  • the organic layer was dehydrated with anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified by preparative TLC.
  • Table 10 13 shows the reaction conditions and intermediates for the compound synthesis in Table 69 above.
  • Mass spectrometry data Mass spectrometry data (EI +); 624 (M) +
  • Solvesso 150 (Exxon Mobil Co., Ltd.) 50 weight?
  • ADDAC 827 (Kay Kasei Co., Ltd.) 0.02 wt%
  • Kidney leaf pieces were inoculated with 4 adult females, Sena mada and female, and laid in a constant temperature room at 25 ° C. After 24 hours, the female adult was removed from the small piece force, and the small piece was immersed in a chemical solution adjusted to 500 ppm with 50% acetone water (added with 0.05% tween20). After air drying, the small piece was placed on agar and left in a constant temperature room at 25 ° C (16 hours light period-8 hours dark period). Six days after the drug treatment, the number of remaining eggs and the number of dead insects were counted, and the egg-killing rate was calculated according to the following formula.
  • Ovulation rate (%) ⁇ (number of remaining eggs + number of dead insects) Z (number of remaining eggs + number of dead insects + number of living insects) ⁇ X 100 [0120]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention décrit un dérivé ayant un excellent effet insecticide/miticide et une composition insecticide/miticide comprenant le dérivé qui présente un effet fiable et peut être utilisé en toute sécurité. La présente invention concerne une composition insecticide/miticide comprenant un composé de la formule (1) ou un sel d’ajout d’acide acceptable du point de vue agricole de celui-ci comme ingrédient actif : (1) dans laquelle R1 représente, de préférence, un atome d’hydrogène, un groupe alkyle en C1-6 ou un atome d’halogène ; R2 représente un groupe hydroxyle ou un groupe alkylcarbonyloxy en C1-6 ; R3 et R4 représentent indépendamment un groupe alcoxy en C1-6 ; R représente un atome d’hydrogène ; W représente un groupe phényloxy qui peut être substitué, un groupe phényle, un groupe benzyloxy ou un groupe phénylthio qui peut être substitué ; X représente un atome d’halogène, un groupe alkyle en C1-6 qui peut être substitué par un atome d’halogène ou un groupe alcoxy en C1-6 ; n est un nombre entier qui vaut 0 ou 1 ; et m est un nombre entier qui vaut 0 ou 1.
PCT/JP2006/312305 2005-06-21 2006-06-20 Nouvel agent insecticide/miticide WO2006137389A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016039048A1 (fr) * 2014-09-10 2016-03-17 日本曹達株式会社 Composé de pyridine et son utilisation
JPWO2017155052A1 (ja) * 2016-03-09 2019-01-17 日本曹達株式会社 ピリジン化合物およびその用途
WO2024005032A1 (fr) * 2022-06-29 2024-01-04 株式会社Adeka Dérivé d'azépandione ou sel de celui-ci, agent de lutte contre les organismes nuisibles contenant ledit composé et procédé d'utilisation associé

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05271010A (ja) * 1992-01-09 1993-10-19 Bayer Ag メルカプトニコチン酸誘導体を基にした除草剤および殺植物線虫剤
JP2000516917A (ja) * 1996-07-24 2000-12-19 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤として使用されるカルボアニリド
JP2005502716A (ja) * 2001-09-21 2005-01-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アントラニルアミド節足動物殺滅剤処理
JP2005511517A (ja) * 2001-09-25 2005-04-28 ビーエーエスエフ アクチェンゲゼルシャフト ニコチンアニリド誘導体の結晶性水和物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH05271010A (ja) * 1992-01-09 1993-10-19 Bayer Ag メルカプトニコチン酸誘導体を基にした除草剤および殺植物線虫剤
JP2000516917A (ja) * 1996-07-24 2000-12-19 バイエル・アクチエンゲゼルシヤフト 有害生物防除剤として使用されるカルボアニリド
JP2005502716A (ja) * 2001-09-21 2005-01-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー アントラニルアミド節足動物殺滅剤処理
JP2005511517A (ja) * 2001-09-25 2005-04-28 ビーエーエスエフ アクチェンゲゼルシャフト ニコチンアニリド誘導体の結晶性水和物

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016039048A1 (fr) * 2014-09-10 2016-03-17 日本曹達株式会社 Composé de pyridine et son utilisation
JPWO2017155052A1 (ja) * 2016-03-09 2019-01-17 日本曹達株式会社 ピリジン化合物およびその用途
US10781177B2 (en) 2016-03-09 2020-09-22 Nippon Soda Co., Ltd. Pyridine compound and use thereof
WO2024005032A1 (fr) * 2022-06-29 2024-01-04 株式会社Adeka Dérivé d'azépandione ou sel de celui-ci, agent de lutte contre les organismes nuisibles contenant ledit composé et procédé d'utilisation associé

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