[go: up one dir, main page]

WO2001044154A1 - Derives de dihalopropenyloxybenzene et pesticides contenant ces derniers en tant qu'ingredients actifs - Google Patents

Derives de dihalopropenyloxybenzene et pesticides contenant ces derniers en tant qu'ingredients actifs Download PDF

Info

Publication number
WO2001044154A1
WO2001044154A1 PCT/JP2000/008870 JP0008870W WO0144154A1 WO 2001044154 A1 WO2001044154 A1 WO 2001044154A1 JP 0008870 W JP0008870 W JP 0008870W WO 0144154 A1 WO0144154 A1 WO 0144154A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
mmol
solvent
halogen atom
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2000/008870
Other languages
English (en)
Japanese (ja)
Inventor
Manabu Katsurada
Shinji Kawata
Nobuo Kyomura
Yasushi Shiga
Toshiki Fukuchi
Risa Yamada
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsubishi Chemical Corp
Original Assignee
Mitsubishi Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsubishi Chemical Corp filed Critical Mitsubishi Chemical Corp
Priority to AU20238/01A priority Critical patent/AU2023801A/en
Publication of WO2001044154A1 publication Critical patent/WO2001044154A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
    • A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
    • 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
    • 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
    • A01N43/80—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 1,2
    • 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
    • A01N43/82—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 three ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
    • C07C239/08—Hydroxylamino compounds or their ethers or esters
    • C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups

Definitions

  • the present invention relates to a dihalopropenyloxybenzene derivative and an intermediate for producing the same, and a pesticidal agent containing the dihalopropenyloxybenzene derivative as an active ingredient.
  • the present invention relates to pesticides, especially insecticides and acaricides in pets.
  • linking group bonded to the dihalopropenyloxyphenyl group is an oxygen atom, a sulfur atom, or an amino group are described.
  • the linking group bonded to the dihalopropenyloxyphenyl group is a compound having a substituent having a carbon atom as a linking group
  • a compound having a carbon atom as a linking group is more preferable than a compound having an oxygen atom, a sulfur atom or an amino group. This is preferable because the variation in synthesizing the compound greatly increases.
  • WO98544848 describes that a compound having a difluoroalkenyl group at a terminal is effective as an insecticide and acaricide, and specific examples thereof are shown below. Although there are examples of compounds having a similar structure,
  • a dihalopropenyloxybenzene derivative having an insecticidal and acaricidal effect is one in which the linking group bonded to the dihalopropenyloxyphenyl group is an oxygen atom, a sulfur atom, or an amino group.
  • the linking group bonded to the dihalopropenyloxyphenyl group is an oxygen atom, a sulfur atom, or an amino group.
  • a substituent having a carbon atom as a linking group is preferable because a variation in the synthesis of a compound is significantly increased, only a limited number of substituents are known. It has not been done yet.
  • the present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, a group of compounds in which the linking group bonded to the dihalopropyloxyphenyl group is a group having a carbon atom. That the compound has insecticidal and acaricidal activity, in particular, as a terminal substituent, an aryloxyaryloxy group, a heterocyclicoxyaryloxy group, an aryloxyheterocyclicoxy group, or a heterocyclic group.
  • Cyclic oxyhetero Compounds having a specific substituent, a cyclic oxy group exhibit high insecticidal and acaricidal effects against insects of the order Coleoptera, such as citrus insects, and are extremely safe for mammals and fish. This led to the completion of the present invention.
  • A represents a hydrogen atom, an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a aryl group which may be substituted or substituted.
  • RR 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an alkenyloxy group, an alkynyloxy group, an alkoxyalkyl group.
  • R 1 and R 2 , R 3 and R 4 , R 5 and R 6 may be taken together to form an alkylidene group or an alkylenedioxy group,
  • ⁇ 1 and ⁇ 2 each independently represent a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group;
  • Y represents a halogen atom, an alkyl group or a haloalkyl group
  • n an integer of 0 to 2
  • Z represents a halogen atom.
  • a pesticidal agent containing the same as an active ingredient, particularly an insecticide and acaricide.
  • Another gist of the present invention is to provide an intermediate of the above-mentioned dihalopropenyloxybenzene derivative represented by the following general formula (II):
  • Q 1 represents a halogen atom, a hydroxyl group, an aminooxy group, an oxyamino group, an alkoxy group, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, an arylsulfonyloxy group or a haloarylsulfonyloxy group.
  • R 5 ′ and R 6 ′ each independently represent a hydrogen atom or an alkyl group, r represents an integer of 9 or less,
  • X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group;
  • Y represents a halogen atom, an alkyl group or a haloalkyl group
  • n an integer of 0 to 2
  • Z represents a halogen atom.
  • Q 2 represents an oxygen atom or a hydroxyimino group
  • Q 3 represents a hydrogen atom, a halogen atom, a hydroxyl group, an amino group, a hydrazino group or an alkyl group;
  • R 5 ′ and R 6 ′ each independently represent a hydrogen atom or an alkyl group, r represents an integer of 9 or less,
  • AI2 each independently represent a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group;
  • Y represents a halogen atom, an alkyl group or a haloalkyl group
  • n an integer of 0 to 2
  • Z represents a halogen atom.
  • the dihalopropenyloxybenzene derivative which is an active ingredient of the insecticide and acaricide of the present invention, is represented by the above general formula (I).
  • A is a hydrogen atom; a methyl group which may be substituted, Ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl
  • An alkynyl group such as an ethynyl group, a butynyl group or a pentenyl group which may be substituted; an aryl group such as a phenyl group or a naphthyl group which may be substituted; or a
  • A is preferably an aryl group or a heterocyclic group which may be substituted, and particularly preferably a phenyl group or a pyridyl group which may be substituted.
  • Examples of the substituent of the alkyl, alkenyl and alkynyl groups described above A is not particularly limited as long as it is a group which does not affect the insecticidal activity, specifically, it includes groups that are tables in G 1.
  • Examples of the group represented by G 1 include a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; a hydroxyl group; an alkoxy group such as a methoxy group, an ethoxy group and an n-butoxy group; a trifluoromethoxy group and a difluoromethoxy group.
  • Haloalkoxy groups such as trifluoroethoxy group; aryl groups such as phenyl group and naphthyl group; aryloxy groups such as phenoxy group and naphthyloxy group; pyridyl group, thiazolyl group, benzothiazolyl group, oxazolyl group, benzoxazolyl.
  • heterocyclic groups such as a group, a furyl group, a phenyl group, a morphyl group, a benzodioxanyl group, and a benzofuranyl group; and a heterocyclic group such as a pyridyloxy group, a furyloxy group, and a thiazolyloxy group.
  • the alkoxy group and haloalkoxy group in G 1 are preferably those having 4 or less carbon atoms.
  • the aryl group, aryloxy group, heterocyclic group and heterocyclic oxy group exemplified in the above G 1 further include a halogen atom, a hydroxyl group, an alkyl group, a haloalkyl group, an alkoxy group, as exemplified above.
  • Examples of the substituent of Ariru heterocyclic group group and the above A is not particularly limited as long as it is a group which can not affect the insecticidal activity, specifically, include groups represented by G 2 .
  • the group represented by G 2 in addition to the substituents exemplified above G 1, Shiano group; methylcarbamoyl group, Echiru group, n- propyl group, iso- propyl, n- butyl group, sec- butyl group Haloalkyl groups such as trifluoromethyl group, difluoromethyl group, trifluoromethyl group, dichlorodifluoroethyl group; formyl group; acyl groups such as methylcarbonyl group and ethylcarbonyl group; Acyloxy groups such as acetooxy group and propanoloxy group; alkoxycarbonyl groups such as methoxycarbonyl group and ethoxycarbonyl group; alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, iso-propylthio group and n-butylthio group.
  • Haloalkylthio groups such as trifluoromethylthio and trifluoroethylthio; methylsulfinyl Alkylsulfinyl groups such as phenyl group, ethylsulfinyl group, n-propylsulfinyl group, iso-propylsulfinyl group and n-butylsulfinyl group; haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and trifluoroethylsulfinyl group Alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, iso-propylsulfonyl group, n-butylsulfonyl group; and trifluoromethylsulfonyl group, trifluoroethylsul
  • Alkyl groups in G 2 a haloalkyl group, an alkoxy group, a haloalkoxy group, ⁇ sill group, Ashiruokishi group, an alkoxycarbonyl group, an alkylthio group, Haroaru Kiruchio group, alkylsulfinyl group, haloalkylsulfinyl group, an alkyl sulfonyl group and haloalkylsulfonyl group Are preferably those having 4 or less carbon atoms.
  • G 2 is preferably a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, an alkylthio group, or a haloalkylthio group. (When two adjacent substituents of these substituents together form And may form a condensed ring with an aryl group or a heterocyclic group.), Or a phenyl group, a phenoxy group, or a phenylthio group.
  • pyridyl group, pyridyloxy group or pyridylthio group are a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, Select from the group consisting of alkylthio and haloalkylthio May be substituted with substituents) it is.
  • Ariru groups exemplified above G 2 Ariruokishi group, Ariruchio group, heterocyclic group, heterocyclic Okishi group and heterocyclic Chio group further that looks as though it exemplified above, halogen atom, hydroxyl group, Shiano group
  • R 7 and R 8 each independently represent a hydrogen atom or an alkyl group, and preferably have 4 or less carbon atoms as the alkyl group.
  • R 9 and R 1Q each independently represent a hydrogen atom or an alkyl group, and preferably has 4 or less carbon atoms as the alkyl group.
  • R 12, R 13 , R 14, R 15, R 16, R 17 and R 18, which it independently hydrogen atom; a fluorine atom, a chlorine atom A halogen atom such as a bromine atom; a methyl group, an ethyl group, an n -propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, It is a linear, branched or cyclic alkyl group such as a cyclic propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group or the like, and the alkyl group preferably has 6 or less carbon atoms.
  • R 12 to R 18 are preferably a hydrogen atom, a methyl group or an ethyl group.
  • RR 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom; methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl
  • a chain, branched or cyclic alkyl group such as a tert-butyl group, an n-pentyl group, an n-hexyl group, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group
  • a chain, branched or cyclic alkenyl group such as an enyl group, a butenyl group, and a hexenyl group
  • an alkynyl group such as an ethynyl group, a petenyl group, and a pentynyl group
  • Alkoxy group alkenyloxy group such as propenyloxy group
  • RR 2 , RR 4 , R 5 and R 6 are preferably a hydrogen atom, a methyl group or an ethyl group.
  • p, q and r are integers, preferably 5 or less, particularly preferably 3 or less.
  • X 1 and X 2 are each independently a hydrogen atom; a fluorine atom, a chlorine atom, a halogen atom such as a bromine atom; a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group And alkyl groups such as sec-butyl group, t-butyl group, etc .; or haloalkyl groups such as trifluoromethyl group, difluoromethyl group, trichloromethyl group and dichlorodifluoroethyl group. Those having 4 or less carbon atoms are preferred.
  • X 1 and X 2 are preferably a halogen atom or an alkyl group, and particularly preferably a halogen atom or a methyl group.
  • Z represents a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom, and is preferably a chlorine atom. Z may be different halogen atoms.
  • the A—W— group may be substituted, and may be an aryl group such as a phenoxy phenoxy group.
  • heterocyclic oxyaryloxy group such as pyridyloxyphenoxy group; optionally substituted An aryloxy heterocyclic oxy group such as a phenoxypyridyloxy group; or an optionally substituted heterocyclic oxy group such as a pyridyloxypyridyloxy group.
  • Substituents for the above aryloxyaryl, heterocyclic oxyaryloxy, aryloxyheterocyclic oxy and heterocyclic oxyheterocyclic oxy groups are each independently And a halogen atom, a hydroxyl group, a cyano group, an alkyl group, a haloalkyl group, an alkoxy group, a haloalkoxy group, a formyl group, an acyl group, an acyloxy group, an alkoxycarbonyl group, an alkylthio group, a haloalkylthio group, an alkyl group A sulfinyl group, a haloalkylsulfinyl group, an alkylsulfonyl group, and a haloalkylsulfonyl group, preferably a haloalkyl group, a haloalkoxy group, or a haloalkylthio group.
  • alkyl group, haloalkyl group, alkoxy group, haloalkoxy group, acyl group, acyloxy group, alkoxycarbonyl group, alkylthio group, haloalkylthio group, alkylsulfinyl group, haloalkylsulfinyl group, alkylsulfonyl group and haloalkylsulfonyl group are preferable.
  • A—W— group examples include a 4- (3-trifluoromethyl-1-pyridyloxy) phenoxy group, a 4- (4-trifluoromethyl-12-pyridyloxy) phenoxy group, and a 4- (5- Trifluoromethyl-1- (2-pyridyloxy) phenoxy group, 4- (4-trifluoromethylphenoxy) phenoxy group, 4- (3-trifluoromethylphenoxy) phenoxy group, 4— (4— Trifluoromethoxyphenoxy) phenoxy group and the like.
  • the compound of the present invention represented by the general formula (I) can be produced by combining known reactions.
  • the compound can be efficiently produced. Can be manufactured.
  • L is a halogen atom such as a chlorine atom, a bromine atom and an iodine atom; an alkylsulfonyloxy group such as a methanesulfonyloxy group and an ethanesulfonyloxy group; or a benzenesulfonyloxy group and P-toluenesulfonyl Oxy group And represents a reelsulfonyloxy group, preferably a chlorine atom, a bromine atom, a methanesulfonyloxy group, or a P-toluenesulfonyloxy group.
  • R 19 is a hydrogen atom; methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, n-pentyl, n-hexyl, cyclopropyl building group, a cyclobutyl group, a cyclopentyl group, a linear, branched or cyclic alkyl group such as a cyclohexyl group, a, W, X 1, X 2, Y, Z, RR 2, R 3, R 4, R 5, R 6, R 9 , R 12, R 13, R 14, R 15, n, p, q and r are the as defined in one general formula (I).
  • the dihaloprovenyloxybenzene derivative represented by the general formula (la) can be produced by the method of the following Reaction Formula 1 or 2.
  • the dihalopropenyloxybenzene derivative of the general formula (la) can be obtained by reacting the oxime derivative (IV) with a halogen derivative or a sulfonate derivative (Ila) in an inert solvent in the presence of a base.
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide; Metal tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alcoholates such as sodium methylate
  • alkali metal carbonates such as carbon dioxide
  • Metal tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • a quaternary catalyst such as tetra-n-butylammonium bromide to the reaction system.
  • a catalyst such as a ammonium salt or a crown ether such as 18-crown-6-ether may be added in an amount of 0.01 to 1 equivalent to the oxime derivative (IV).
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like
  • the halogen derivative or sulfonate derivative (Ila) used in the reaction is 0.5 to 0.5% of the oxime derivative (IV).
  • the reaction is carried out at 0 to 150 ° C, preferably 10 to 100 ° C, in an amount of up to 10 equivalents, preferably 1 to 3 equivalents.
  • the dihalopropenyloxybenzene derivative of the general formula (la) can also be obtained by subjecting a carbonyl derivative (V) and an oxamine derivative (lib) to a dehydration reaction in an inert solvent.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; Esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol
  • -Polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, acetonitrile, acetic acid, and other polar solvents or water. Is also good. Of these, alcohols such as methanol and ethanol are preferred.
  • the oxyamine derivative (lib) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the carbonyl derivative (V), and is used at 0 to 100 ° C, preferably 10 ° C to The reaction takes place at the boiling point.
  • the dihalopropenyloxybenzene derivative represented by the general formula (lb) can be produced by the method of the following reaction formula 3 or 4.
  • the dihalopropenyloxybenzene derivative represented by the general formula (lb) can be obtained by reacting a oxime derivative (Ilia) with a halogen derivative or a sulfonate derivative (VI) in an inert solvent in the presence of a base.
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide rim; Metal hydroxides such as potassium rim; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alcoholates such as sodium methylate
  • alkali metal carbonates such as carbon dioxide rim
  • Metal hydroxides such as potassium rim
  • tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • a quaternary catalyst such as tetra-n-butylammonium bromide to the reaction system.
  • a catalyst such as ammonium salt or a crown ether such as 18-crown-6-ether may be added in an amount of 0.01 to 1 equivalent to the oxime derivative (Ilia).
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol, and propanol; ketones such as acetone and methylethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylbiphenyl Examples thereof include polar solvents such as don, dimethylsulfoxide, and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the
  • the halogen derivative or sulfonate derivative (VI) used in the reaction is 0.5 to 10% more than the oxam derivative (Ilia).
  • the reaction is carried out at a double equivalent, preferably 1 to 3 equivalents, at 0 to 150 ° C, preferably 10 to 100 ° C.
  • the dihalopropenyloxybenzene derivative of the general formula (lb) can also be obtained by subjecting a carbonyl derivative (Illb) and an oxamine derivative (VII) to a dehydration reaction in an inert solvent.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; Esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetonitrile, acetic acid, and water. It may be a single solvent or a mixed solvent. Of these, alcohols such as methanol and ethanol are preferred.
  • the oxyamine derivative (VII) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the carbonyl derivative (Illb), and 0 to: 100 ° C, preferably 10 ° C to the solvent.
  • the reaction is carried out at a boiling point of.
  • the dihalopropenyloxybenzene derivative of the general formula (Ic) is obtained by reacting an alcohol (VIII) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base as shown in Reaction formula-5. Is obtained by reacting an alcohol (VIII) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base as shown in Reaction formula-5. Is obtained by reacting an alcohol (VIII) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base as shown in Reaction formula-5. Is obtained by reacting an alcohol (VIII) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base as shown in Reaction formula-5. Is obtained by reacting an alcohol (VIII) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base as shown in Reaction formula-5. Is obtained by reacting an alcohol (VIII) with
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alkoxides such as sodium methylate; alkali metal alkoxides such as carbonate lime; Metal hydroxides; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alkoxides such as sodium methylate
  • alkali metal alkoxides such as carbonate lime
  • Metal hydroxides such as tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; Esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; polar solvents such as ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, dimethyl sulfoxide, and acetonitrile; and water. It may be a single solvent or a mixed solvent.
  • the alcohol (VIII) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the carboxylic acid chloride (IIIc), and 0 to 150 ° C, preferably 10 ° C to the solvent.
  • the reaction is carried out at a boiling point of.
  • the dihalopropenyloxybenzene derivative of the general formula (Id) can be obtained by reacting an amine (IX) with a carboxylic acid chloride (IIIc) in a solvent in the presence of a base, as shown in Reaction formula-6.
  • bases used are: metal hydrides such as sodium hydride; metal alkoxides such as sodium methylate; metal alkoxides such as carbon dioxide; And the like; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and bicholine.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; ketones such as acetone and methylethyl ketone; ⁇ , ⁇ - Examples thereof include polar solvents such as dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like
  • getyl ether, tetrahydrofuran Ethers
  • the amine (IX) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the carboxylic acid chloride (IIIc), and 0 to: 150 ° C, preferably 10 ° C to The reaction takes place at the boiling point of the medium
  • the dihalopropenyloxybenzene derivative represented by the general formula (Ie) is obtained by halogenating an oxime derivative (Illd) with a halogenating agent in an inert solvent, as shown in Reaction formula-7, and then reacting the olefin derivative in the presence of a base. It is obtained by reacting with (X).
  • halogenating agent examples include chlorine, bromine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, sulfuryl chloride and the like.
  • bases used include: Alkali metal hydrides such as sodium hydride; Alkali metal alcoholates such as sodium methylate; Alkali metal carbonates such as carbonated lime; Metal hydroxides; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; Esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol
  • Ketones such as acetone and methylethylketone; polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and acetonitrile; water; and the like; Or a mixed solvent.
  • polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and acetonitrile
  • water and the like
  • ⁇ , ⁇ -dimethylformamide, tetrahydrofuran, toluene and the like are preferred.
  • the olefin derivative (X) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the oxime derivative (Illd), and 0 to: 150 ° C, preferably 10 to 100 ° C. The reaction takes place.
  • the dihalopropenyloxybenzene derivative of the general formula (If) is obtained by halogenating an oxime derivative (Illd) with a halogenating agent in an inert solvent as shown in Reaction formula-8, and then reacting the acetylene derivative in the presence of a base. Obtained by reacting with (XI)
  • halogenating agent examples include chlorine, bromine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, sulfuryl chloride and the like.
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide; Metal tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alcoholates such as sodium methylate
  • alkali metal carbonates such as carbon dioxide
  • Metal tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, ⁇ , ⁇ -dimethylformamide, tetrahydrofuran, toluene and the like are preferred.
  • the acetylene derivative (XI) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the oxime derivative (Illd), and 0 to: L50 ° C, preferably 10 to 100 °.
  • the reaction takes place at C.
  • the dihalopropenyloxybenzene derivative of the general formula (Ig) can be prepared by converting the ester derivative (XII) and the benzamidoxime derivative (Ille) in an inert solvent in the presence of an acid or a base, as shown in Reaction Scheme_9. It is obtained by a condensation reaction.
  • acids used include brenstead acid such as hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, pyridinium p-toluenesulfonic acid, or tertiary acid.
  • Examples thereof include Lewis acids such as aluminum chloride, boron tribromide, and boron trichloride.
  • the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide; And the like; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and bicholine.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, solvents such as toluene and tetrahydrofuran are preferred.
  • the ester derivative (XII) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the benzamidoxime derivative (Hie), and 0 to 150 ° C, preferably 10 to 100.
  • the reaction is performed at ° C.
  • the dihalopropenyloxybenzene derivative of the general formula (Ii) undergoes a dehydration reaction between an alcohol (VIII) and an oxadiazolinone derivative (Ih) in a solvent, as shown in Reaction Formula-10. It can be obtained by: Examples of the reagent for performing the dehydration reaction include triphenylphosphine and getyl azodicarbonate.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene and xylene; halogen hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; ethers such as getyl ether, tetrahydrofuran and dioxane.
  • Esters such as ethyl acetate; ketones such as acetone and methyl ethyl ketone; polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide and acetonitrile; It may be a solvent or a mixed solvent.
  • the alcohol (VIII) used in the reaction is used in an amount of 0.5 to: 10 equivalents, preferably 1 to 3 equivalents to the oxadiazolinone derivative (Ih), and 0 to: 150 ° C, preferably 10 to 10 equivalents.
  • the reaction takes place at 100 ° C.
  • the dihalopropenyloxybenzene derivative represented by the general formula (Ii) can be obtained by converting the compound (VI) and the oxadiazolinone derivative (Ih) in a solvent in the presence of a base, as shown in Reaction Formula-11.
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide; Metal tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alcoholates such as sodium methylate
  • alkali metal carbonates such as carbon dioxide
  • Metal tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, N, N-dimethylformamide, tetrahydrofuran, toluene and the like are preferred.
  • the compound (VI) used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the oxadiazolinone derivative (Ih), and 0 to: 150 ° C, preferably 10 to 10 equivalents.
  • the reaction takes place at ⁇ 100 ° C.
  • the compounds represented by the general formulas (II) and (III) are useful intermediates for producing the compound represented by the general formula (I), as shown in the above Reaction Formulas 1-1 to 11.
  • Q 1 represents a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom; a hydroxyl group; an aminooxy group; an oxyamino group; an alkoxy group such as a methoxy group, an ethoxy group, and an n-butoxy group; Alkylsulfonyloxy group such as methanesulfonyloxy group; haloalkylsulfonyloxy group such as trifluoromethanesulfonyloxy group; arylsulfonyloxy group such as benzenesulfonyloxy group and p-toluenesulfonyloxy group; Or a haloarylsulfonyloxy group such as a p-chloro benzenesulfonyloxy group, preferably a halogen atom or an aminooxy group, particularly preferably a bromine atom or
  • R 5 ′ and R 6 ′ are each independently a hydrogen atom; or a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a t-butyl group, etc.
  • the alkyl group is preferably an alkyl group having 4 or less carbon atoms.
  • r is an integer of 9 or less, preferably 5 or less, particularly preferably an integer of 3 or less It is.
  • X 1 , X 2 S Y, Z and n are the same as those described in the general formula (I).
  • Q 2 is an oxygen atom or a hydroxyimino group
  • Q 3 is a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom; a hydroxyl group; an amino group; a hydrazino group; or a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, It is an alkyl group such as an n-butyl group, a sec-butyl group and a t-butyl group, and the above-mentioned alkyl group is preferably one having 4 or less carbon atoms.
  • R 5 ′ and R 6 ′ are each independently a hydrogen atom; or a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, a t-butyl group
  • the alkyl group is preferably an alkyl group having 4 or less carbon atoms.
  • r represents an integer of 9 or less, preferably 5 or less, more preferably 3 or less, and particularly preferably 0.
  • X 1 , X 2 , Y, ⁇ , and ⁇ are the same as those described in the general formula (I).
  • the compounds represented by the general formulas (II) and (III) can be produced by combining known reactions.
  • X 1 , X 2 , Y, ⁇ , and ⁇ are as defined in the general formula (I), and L is as defined in the aforementioned reaction formula-1.
  • the phenol derivative (XIII) is brominated with bromine, and the resulting 4-bromophenol derivative (XIV) is reacted with chloromethyl methyl ether in the presence of a base to give a 4-methoxymethoxybromobenzene derivative (XV).
  • the 4-methoxy methoxy bromobenzene derivative (XV) is reacted with ⁇ , ⁇ -dimethylformamide by a Grignard reaction to obtain a 4-methoxy methoxy benzoaldehyde derivative (XVI). it can.
  • the 4-methoxymethoxybenzaldehyde derivative (XVI) is hydrolyzed with an acid such as hydrochloric acid to give a phenol derivative (XVII).
  • the aldehyde derivative (Illb ′) can be obtained by reacting the above-mentioned phenol derivative (XVII) with a trihalopropene derivative or a sulfonyloxydihaprobenyloxybenzene derivative (XVHI) in an inert solvent in the presence of a base. .
  • bases used are: metal hydrides such as sodium hydride; metal alkoxides such as sodium methylate; alcohols such as carbon dioxide Metal hydroxides; metal hydroxides such as lithium hydroxide; tertiary amines such as N-methylmorpholine and triethylamine; aromatic bases such as pyridine and picoline.
  • a catalyst such as a quaternary ammonium salt such as tetra-n-butylammonium bromide or a crown ether such as 18-crown-6-ether may be added to the reaction system for the oxime derivative (IV). You may add 0.01 to 1 equivalent.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, dioxane, and the like.
  • Ethers such as ethyl acetate; alcohols such as methanol, ethanol, and propanol; ketones such as acetone and methyl ethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, and dimethyl sulfoxide.
  • a polar solvent such as acetonitrile or water
  • the solvent may be a single solvent or a mixed solvent.
  • polar solvents such as ⁇ , ⁇ -dimethylformamide and acetonitrile are preferred.
  • C The trihalopropene derivative or sulfonyloxydihalopopenyloxybenzene derivative (XVIII) used in the reaction is a phenol derivative. It is used in an amount of 0.5 to: 10 equivalents, preferably 1 to 3 equivalents to (XVII), and the reaction is carried out at 0 to 150 ° C, preferably 10 to 100 ° C.
  • the oxime derivative (Hid) can be obtained by reacting the aldehyde derivative (nib ') with hydroxyamine hydrochloride or sulfate in an inert solvent in the presence of a base.
  • Examples of the base to be used include: Al metal hydrides such as sodium hydride; Alkali metal alcohols such as sodium methylate; Al metal alkali acetate such as acetic acid lime; Carbonate lime, etc.
  • alkali metal acetates such as potassium acetate
  • alkali metal carbonates such as potassium carbonate
  • tertiary amines such as triethylamine
  • aromatic bases such as pyridine are preferable.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolid
  • Examples thereof include polar solvents such as don, dimethyl sulfoxide, and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • the hydroxyamine hydrochloride or sulfate used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the aldehyde derivative (Illb '), and the base is an aldehyde derivative (Illd).
  • the reaction is carried out at 0.5 to 10 equivalents, preferably 1 to 3 equivalents, 0 to: 150 ° C, preferably 10 ° C to the boiling point of the solvent.
  • the dihalopropenyloxybenzene derivative represented by the general formula (Ille) can be obtained by halogenating the above oxime derivative (Illd) with a halogenating agent in an inert solvent and reacting with ammonia in the solvent.
  • halogenating agent examples include chlorine, bromine, N-chlorosuccinic acid imide, N-bromosuccinic acid imide, sulfuryl chloride and the like.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, ether, N, N-dimethylformamide, tetrahydrofuran, methanol and the like are preferable.
  • the halogenating agent used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the oxime derivative (Illd), and 0 to: 150 ° C, preferably 10 to;
  • the ammonia is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the oxime derivative (Illd), and the reaction is carried out at 0 to 150 ° C, preferably 10 to 100 ° C. .
  • the carboxylic acid derivative (Illf) can be obtained by oxidizing the aldehyde derivative (Illb ′) obtained by the method of Reaction Scheme-12 in an inert solvent.
  • Examples of the oxidizing agent used include oxides of heavy metals such as sodium dichromate and lithium permanganate; and chlorinated oxides such as sodium chlorite.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • polar solvents such as acetonitrile, tetrahydrofuran, and water are preferred.
  • the oxidizing agent used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the aldehyde derivative (Illb '), and the reaction is carried out at 0 to 150 ° C, preferably 10 to 100 ° C. Will be
  • the acid chloride derivative (IIIc) is obtained by halogenating the carboxylic acid derivative (Illf) in an inert solvent.
  • halogenating agent examples include halogenating agents such as thionyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphoryl chloride, oxalyl chloride, and phosgene.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; polar solvents such as ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, dimethylsulfoxide, and acetonitrile; water; and the like; May also be a mixed solvent. Of these, solvents such as dichloromethane are preferred.
  • the halogenating agent used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the carboxylic acid derivative (Illf), and 0 to: 150 ° C, preferably 10 to 100 ° C.
  • the reaction takes place.
  • the acyl hydrazide derivative (Illg) is obtained by hydrazide of an acid chloride derivative (IIIc) with hydrazine, hydrazine monohydrate, etc. in an inert solvent as shown in Reaction Scheme-13. can get.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, and acetonitrile, or water, and the like. May also be a mixed solvent. Of these, solvents such as tetrahydrofuran are preferred.
  • the hydrazine reagent used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the acid chloride derivative (IIIc), and 0 to: 150 ° C, preferably 10 to: 100 °.
  • the reaction takes place at C.
  • the oxadiazolinone derivative (Ig) can be obtained by adding the hydrazide derivative (Illg) to an inert solvent in the presence of a base in an inert solvent such as phosgene, diphosgene, triphosgene, carbonyldimidazole, or carbonate. It is obtained by reacting with an agent.
  • bases used include: Alkali metal hydrides such as sodium hydride; Alkali metal alcoholates such as sodium methylate; Alkali metal acetates such as acetic acid rim; Carbonate rim; Metal hydroxides such as potassium hydroxide; tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • Alkali metal acetates such as potassium acetate
  • alkali metal carbonates such as potassium carbonate
  • tertiary amines such as triethylamine
  • aromatic bases such as pyridine are preferable.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, ethers such as tetrahydrofuran are preferred.
  • the carboxylating agent used in the reaction is 0.5 to 10 equivalents, preferably 1 to 3 equivalents, based on the hydrazide derivative (Illg), and the base is 0.5 to 10 equivalents based on the hydrazide derivative (Illg).
  • the reaction is carried out at a double equivalent, preferably 1 to 3 equivalents, 0 to: 150 ° C, preferably 10 ° C to the boiling point of the solvent. Reaction formula 1 1 4
  • X lib 'alcohol derivative (lie) can be obtained by reacting an aldehyde derivative (Illb') obtained by the method of Reaction Scheme 11 with a reducing agent in an inert solvent.
  • Examples of the reducing agent used include lithium aluminum hydride, sodium borohydride and the like.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol
  • Ketones such as acetone and methylethyl ketone; polar solvents such as ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, dimethylsulfoxide, and acetonitrile, or water, and the like. Or a mixed solvent.
  • polar solvents such as ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, dimethylsulfoxide, and acetonitrile, or water, and the like.
  • ethers such as getyl ether, tetrahydrofuran, and dioxane
  • alcohols such as methanol, ethanol, and propanol are preferable.
  • the reducing agent used in the reaction was 0 ::! With respect to the aldehyde derivative (Illb '). ⁇ 5 times
  • the reaction is carried out at a temperature of -20 to 100 ° C, preferably 0 ° C to the boiling point of the solvent.
  • the halide derivative (Ila ') is obtained by reacting an alcohol derivative (lie) with a halogenating agent in a solvent-free or inert solvent.
  • halogenating agents include tetrabutylammonium fluoride (TBAF), sulfur tetrafluoride, getylamino sulfur trifluoride, morpholino sulfur trifluoride, thionyl chloride, phosphorus trichloride, phosphorus pentachloride, Hydrochloric acid, phosphorus oxychloride, hydrobromic acid, phosphorus tribromide, thionyl bromide, or a composite reagent of carbon tetrachloride and triphenyliphosphine, a composite reagent of carbon tetrabromide and triphenyliphosphine, etc.
  • TBAF tetrabutylammonium fluoride
  • sulfur tetrafluoride getylamino sulfur trifluoride
  • morpholino sulfur trifluoride thionyl chloride
  • phosphorus trichloride phosphorus pentachloride
  • Hydrochloric acid phosphorus oxych
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane are preferred.
  • the halogenating agent used in the reaction is used in an amount of 0.1 to 5 equivalents, preferably 0.2 to 2 equivalents, relative to the alcohol derivative (lie), and has a boiling point of -20 to 100 ° C, preferably 0 to 100 ° C.
  • the reaction takes place at a temperature.
  • the sulfonate derivative (Ila ′) can be obtained by reacting the alcohol derivative (lie) with a sulfonylating agent in the absence of a solvent or in an inert solvent in the presence of a base.
  • sulfonylating agent examples include methanesulfonyl chloride, p-toluenesulfonyl chloride, methanesulfonic anhydride, trifluoromethanesulfonic anhydride and the like.
  • bases used are: metal hydrides such as sodium hydride; Alkali metal carbonates such as carbonated lime; Alkali metal hydroxides such as hydroxylated lime; Tertiary amines such as N-methylmorpholine and triethylamine; Aromatic bases such as pyridine and picolin.
  • metal hydrides such as sodium hydride
  • Alkali metal carbonates such as carbonated lime
  • Alkali metal hydroxides such as hydroxylated lime
  • Tertiary amines such as N-methylmorpholine and triethylamine
  • Aromatic bases such as pyridine and picolin.
  • a halide derivative (Ila ′) may be added to the reaction system by adding a halide of an alkali metal such as lithium chloride or lithium bromide.
  • solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; dimethyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane are preferred.
  • the sulfonylating agent used in the reaction is used in an amount of 0.1 to 5 equivalents, preferably 0.2 to 2 equivalents to the alcohol derivative (lie), and is used at a temperature of -20 to 100 ° C, preferably 0 ° C to the solvent.
  • the reaction takes place at the boiling point.
  • the oxamine derivative (lib ') can be obtained by reacting the halogen derivative or the sulfonate derivative (Ila') with acetohydroxamic acid in an inert solvent in the presence of a base.
  • Examples of the base to be used include: alkali metal hydrides such as sodium hydride; alkali metal alcohols such as sodium methylate; alkali metal carbonates such as carbon dioxide; lithium metal hydroxide; Metal tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and picoline.
  • alkali metal hydrides such as sodium hydride
  • alkali metal alcohols such as sodium methylate
  • alkali metal carbonates such as carbon dioxide
  • lithium metal hydroxide lithium metal hydroxide
  • Metal tertiary amines such as N-methylmorpholine and triethylamine
  • aromatic bases such as pyridine and picoline.
  • a catalyst such as a quaternary ammonium salt such as tetra-n-butylammonium bromide or a crown ether such as 18-crown-6-ether may be added to the reaction system as a halogen derivative or sulfonate derivative ( Ila ') Is also good.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; and getyl ether, tetrahydrofuran and dioxane.
  • Ethers such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide.
  • a polar solvent such as acetonitrile or water, and the solvent may be a single solvent or a mixed solvent. Of these, alcohols such as ethanol are preferred.
  • the acetate hydroxamic acid used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the halogen derivative or the sulfonate derivative (Ila ′), and 0 to: 150 ° C., preferably The reaction is carried out at a temperature between 10 ° C and the boiling point of the solvent.
  • the oxamine derivative (lib ') can also be obtained by reacting the fluorimide derivative (XVIII) with hydrazine in an inert solvent.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methylethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent. Of these, alcohols such as ethanol are preferred.
  • the hydrazine used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents, based on the phthalimide derivative (XVIII), and 0 to 150 ° C, preferably 10 ° C to the boiling point of the solvent.
  • the reaction takes place.
  • the fluoroimide derivative (XVIII) is obtained by reacting a halogen derivative or a sulfonate derivative (Ila ') with N-hydroxyfluorimide in an inert solvent in the presence of a base.
  • a base examples include: alkali metal hydrides such as sodium hydride; alkali metal alcoholates such as sodium methylate; alkali metal carbonates such as carbon dioxide; Metal tertiary amines such as N-methylmorpholine and triethylamine; and aromatic bases such as pyridine and bicholine.
  • a catalyst such as a quaternary ammonium salt such as tetra-n-butylammonium bromide or a crown ether such as 18-crown-6-ether may be added to the reaction system as a halogen derivative or sulfonate derivative (Ila. ') May be added in an amount of 0.01 to 1 equivalent.
  • Examples of the solvent used include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; N, N-dimethylformamide, N-methylpyrrolidone; Examples thereof include polar solvents such as dimethyl sulfoxide and acetonitrile, and water, and may be a single solvent or a mixed solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene
  • halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like
  • N-hydroxyphthalimide used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the halogen derivative or the sulfonate derivative (Ila ′), and is preferably 0 to 150 ° C. Is from 10 to: The reaction is carried out at 100 ° C.
  • the fluorimidide derivative (XVIII) can also be obtained by reacting an alcohol derivative (lie) with N-hydroxy fluorimidide in an inert solvent in the presence of a dehydrating agent.
  • dehydrating agents used include trifenylphosphine and getylazodicarboxylate.
  • the solvent used examples include aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and the like; getyl ether, tetrahydrofuran, Ethers such as dioxane; Esters such as ethyl acetate; alcohols such as methanol, ethanol and propanol; ketones such as acetone and methyl ethyl ketone; ⁇ , ⁇ -dimethylformamide, ⁇ -methylpyrrolidone, dimethyl sulfoxide, acetonitrile and the like
  • Examples thereof include a polar solvent and water, which may be a single solvent or a mixed solvent.
  • aromatic hydrocarbons such as benzene, toluene, and xylene, and ethers such as getyl ether, tetrahydrofuran, and dioxane are prefer
  • the ⁇ -hydroxyfluoroimide used in the reaction is used in an amount of 0.5 to 10 equivalents, preferably 1 to 3 equivalents to the alcohol derivative (lie), and is used at -20 to 150 ° C or 0 to The reaction is carried out at a temperature between ° C and the boiling point of the solvent.
  • the pest control agent comprising the compound of the present invention as an active ingredient has an effect of controlling pests, mites, and other pests. It is effective in repelling pests, controlling and controlling pests in a wide range of situations.
  • the compound of the present invention is used to repel or eliminate harmful organisms in agriculture, forestry, etc., specifically when cultivating crops, crops, trees, ornamental plants, etc., and in public health situations. ⁇ Excellent effect as insecticide and acaricide used for pest control.
  • the pests specifically exemplified are not limited to the target pests, and the exemplified pests also include adults, larvae, eggs, and the like.
  • the compound of the present invention can be used for agricultural crops such as food crops (rice, wheat, corn, potatoes, sweet potatoes, beans, etc.), vegetables (brassaceae crops, burrs, eggplants, tomatoes, leeks, etc.), fruit trees (citrus fruits, apples, etc.). , Grapes, thighs, etc., special crops (tobacco, tea, sugar beet, sugar cane, cotton, olive, etc.), pasture and feed crops (sorghum, grasses, legumes, etc.) and ornamental plants ( Damage to plants, flowers, garden trees, etc.) It is effective for repelling and controlling arthropods such as arthropods, molluscs, nematodes and various fungi, especially arthropods such as insects and mites.
  • arthropods such as arthropods, molluscs, nematodes and various fungi, especially arthropods such as insects and mites.
  • the compound of the present invention is a pest repellent when storing harvested products from the above-mentioned crops, for example, cereals, fruits, tree nuts, spices, tobacco, and the like, and products that have been subjected to drying, powdering, and the like. It is also effective for extermination. It is also effective in protecting standing trees, fallen trees, processed timber, stored timber, and the like from damage by pests such as termites and beetles.
  • arthropod phylum insects include, for example, those belonging to the phylum Arthropoda, Mollusca and Nematoda: Examples of arthropod phylum insects include the following.
  • the family Noctuidae such as Lotus sycamore, Tobacco beetle, Noctuida japonica, and the evening squirrel; Suga family such as Convolvulus; the Anophelesaceae family such as Cyanococcus serrata and Papilio persicae; Laminariaceae, such as the lycopogon moth moth; Linguridae, such as the lycopodium moth; Laceae, such as the stag beetle; Skashibaga, such as Kosukashiba; Lingiberidae; Lingiberidae such as Kobomimeiga, Nikameichiyu, and Suzuki Helichronogium; Laceae family such as Ichimondisseri; Laceae family such as Papilio japonica; E Sphingidae such as Garasuzume; Mont black killer whale pike killer whale pike moth family
  • the Coleoptera for example, Scarabaeidae, such as Scarabaeidae, Koohanamuguri, and Mamekogane; Occupiidae, such as Citrus longiflora; Occidental Beetle, such as Marcavix beetle; and Coccinellidae, such as Nijyahoshtentu; Coleoptera, Chrysomelidae such as Budtra kamikiri; Chrysomelidae, Chrysomelidae beetle, Rice beetle; And the like.
  • Scarabaeidae such as Scarabaeidae, Koohanamuguri, and Mamekogane
  • Occupiidae such as Citrus longiflora
  • Occidental Beetle such as Marcavix beetle
  • Coccinellidae such as Nijyahoshtentu
  • Coleoptera Chrysomelidae such as Budtra kamikiri
  • the Hemiptera for example, the insects belonging to the order Coleoptera, Scarabaeidae, and the beetles; the beetle family such as the pear beetle; the helicopteridae such as the beetle; the beetle family such as the spider beetle; Berberidae family, such as Nashigumbai, etc .; Memphiidae family, such as Usumi doremikuragame; Lepidoptera, such as Leafhoppers such as Black-headed Leafhoppers; Scarletidae, such as Black-bellied mosquitoes and Tobira-kuronuka; Obahagoromo, such as Aobahagoromo; Phyllomorphidae, such as pear lice; Whitefly, Silverleaf whitefly, etc.
  • Whiteflies such as Krysius aphid; Apples, evening aphids, etc .; Aphids; Aphids, such as aphids, momokaa aphids, and okabonoa force aphids; Pterodactylidae, such as Mycariidae; Pterodactylidae, such as rubidium beetle; and Pterodactylidae, such as pear marsupials and porphyra.
  • thrips family such as Citrus thrips, C. japonica, Thrips thrips, etc .
  • Thrips thrips family such as Thysanoptera thrips, rice thrips, etc.
  • Hymenoptera examples include honeybees, such as the force of Prague, honeybees, such as apple honeybees, honeybees, such as honeybees, and honeybees, such as rosehip bees.
  • evening fly such as soybean midge and fly
  • fruit fly such as fruit fly
  • rice fly such as rice fly
  • fly fly such as D. melanogaster
  • An example of the genus may also include a fly of the family, such as a green fly.
  • the Orthoptera includes, for example, grasshoppers such as crickets; crickets such as pine beetles;
  • the tabitidae such as the bark beetle; White-spotted beetles, such as mouth snappers.
  • Examples of the termites include termites such as the evening termites, and examples of the earwigs include examples of the earwigs such as the earwigs.
  • the following can be exemplified as the arthropod phylum crustacea and spiders.
  • the isopod of the crustacean there may be mentioned, for example, the family Acaratidae, such as the cadaver bug.
  • Examples of the acarid mites of the order of the spiders include the family Dermatophagoides, such as Cyanomycocyidae and Cyclamenophycephalidae; Mycidae, such as barley mites; The ceremonies, such as Grape Himehada2; The family Acarinae, such as Citrus saccharidum, the apple saccharidum, and the sarcophagid saccharidum;
  • examples of the gastropods of the gastropods include, for example, the apple ringworm, and the patterns of the eyes include, for example, the African snail, the slug, the slug, the slug, the slug, and the like. it can.
  • the following can be exemplified as the nematode phantom net and the tail net.
  • the genus Reticulidae include, for example, Anguinaceae, such as Imogusarecentiyu; Tirencholinex, such as Namiikusekisenyu; Bratyrenchus, such as Kiyu Negusarecentiyu, and Minamigusareceiyu; Heterodela family such as potato cysts; Melody doginae such as Saccharomyces mori; Crykonema family such as ⁇ Cenyuyu; Nototilenic family such as Ichigomecenyu; and Aferencoides family such as strawberry Examples can be given.
  • Examples of the order Gastropodidae include Longidraceae, such as P. elegans, and Trichodulaceae, such as Yumiharicenti. Further, the compound of the present invention is also effective for repelling, controlling and controlling pests that damage trees or affect the vigor of natural forests, plantations and urban green spaces. In such a situation, specific pests include the following. Examples of the arthropod phylum Insecta and Arachnida include the following.
  • Lepidoptera examples include, but are not limited to, such as cephalopoda, gypsy moth, etc .; kalehaga family, such as makkaleha and tsukakareha; mephidae family, e.g., larch; Hirrigidae, such as P. crispinae; Moglitiviga, such as Shimoglitibiga;
  • Scarabaeidae such as Scarabae beetle and Nagachacogane
  • Pentatomidae such as Pseudocarabidae
  • Cerambycidae such as pine beetle
  • Chrysomelidae such as cedar beetle
  • Scorpion beetle Of the worms, such as the weevil family; the weevil family, such as the weevil family; the bark beetle family, such as the pine bark beetle and the bark beetle;
  • the Hemiptera includes, for example, aphid family such as Todomiao aphid; mosquito aphid family such as Ezomatsu cassabra; marsupiidae family such as cedar marcae aphid;
  • Hymenoptera examples include honeybees, such as the stag beetle; honeybees, such as the pine sawfly; and honeybees, such as the chestnut bee.
  • dipteran can include, for example, the mothflies, such as the giant squirrel, etc .; the genus Flies, e.g.
  • spiders of the order Arachnida include, for example, Suginohadani and Todoma nohadani.
  • the order of the Nematodes of the Nematode Nematoda there may be mentioned, for example, the family Parasitidae, such as P. japonicus.
  • the pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in combination with other active compounds such as insecticides, pesticides, and the like in preparations that are effective in the agricultural and forestry situations described above, and in any use forms prepared by the preparations. It can be used in combination with or as a mixture with mites, nematicides, fungicides, synergists, plant conditioners, herbicides and poison baits. More Illustrative active compounds include, but are not limited to, the following.
  • Active compounds such as insecticides and acaricides:
  • organic phosphorus agent examples include dichlorvos, funitrothion, malathion, naled, chlorpyrifos, diazinon, tetrachlorovinphos, fenthion, isoxathion, methidathion, salicion, acephate, dimetone-S-methyl, disulfoton, monochlorthophos, azidinphosimesil. Hosalon, pirimiphos-methyl, protiphos and the like.
  • Examples of the carbamate include metocalp, fenobucalp, propoxur, kyarvalyl, ethiofencarp, pirimicarb, bendiocalp, carbosulfan, carbofuran, mesomil, thiodicarp and the like.
  • Examples of the organic chlorine agent include lindane, DDT, endosulfan, aldrin, chlordane and the like.
  • Pyrethroids include, for example, permethrin, cypermethrin, deltamethrin, cyhalothrin, cyfluthrin, aclinatrin, fenvalerate, etofenprox, silafluofen, fluvalinate, flucitrinate, bifenthrin, arelesrin, phenothrin, fenpropatrine Phosphorus, sifenotrin, framethrin, resmethrin, transfluthrin, praletrin, flufenprox, halofanprox, imiprotrin and the like can be mentioned.
  • Neonicotinoid agents include, for example, imidacloprid, nitembiram, acetamiprid, tefuranitodine, thiamethoxam, thiacloprid and the like.
  • insect growth regulators such as fenylpenzyl perea
  • examples of insect growth regulators include diflubenzuron, clomouth fluazuron, triflumuron, flufenoxuron, hexaflumuron, lufenuron, tefluvenzuron, buprofezin, tebufenozide, chromafufenozide, methoxfenozide.
  • Cyromazine and the like can be mentioned.
  • Juvenile hormone agents include, for example, pyriproxyfen, phenoxycarp, Soprene, hydroprene and the like can be mentioned.
  • Insecticidal substances produced by microorganisms include, for example, abamectin, milbemectin, nikkomycin, emamectin penzolate, ivermectin, subinosad and the like.
  • insecticides examples include cartap, bensultap, chlorf Xnabil, diafentiuron, nicotine sulfate, methaldehyde, fipronil, pimetrozine, indoxacarp, tolfenpyrad and the like.
  • Active compounds for acaricides include, for example, dicophor, phenylisobromolate, benzomate, tetradiphone, polynactin complex, amitraz, propargyl, fenbutin oxide, tricyclohexyltin hydroxide, tefenfenvirad, pyridapen, fenpyroximate, Pyrimidifen, fenazaquin, clofentegine, hexthiazox, acequinosyl, quinomethionate, phenothocalp, ethoxazole, bifenazate and the like can be mentioned.
  • Examples of the nematicide active compound include methyl isocyanate, phosphatiazate, oxamil, and mesulfenphos.
  • Examples of the bait include monofluoroacetic acid, perfurin, coumatetralyl, difacine and the like.
  • Active compounds for fungicides include, for example, inorganic copper, organocopper, sulfur, maneb, thiuram, thiadiazine, captan, closanilonil, iprobenphos, thiophanatemethyl, benomyl, thiabendazol, iprodione, procymidone, dicyclone , Metalaxyl, sandphan, bileton, triflumizole, fenarimol, triforine, dithianon, triazine, fluazinam, probenazole, dietofencarp, isoprothiolane, pyroquilon, iminoc quinoline acetate, eclomethol, dazomet, clesoxime methyl, etc. Can be mentioned.
  • active compounds such as herbicides include bialaphos, sethoxydim, trifluralin, mefenacet and the like.
  • Active compounds of plant regulators include, for example, indolebutyric acid, ethephon, 4-CPA And the like.
  • Active compounds of repellents include, for example, karan-3,4-diol, ⁇ , ⁇ -getyl-m-triamide (Deet), limonene, linalool, citronellal, menthone, hinokitiol, menthol, graniol, u-capitol, etc. Can be mentioned.
  • Examples of the active compound of the synergist include bis- (2,3,3,3-tetrachloropropyl) ether and N- (2-ethylhexyl) bisque [2,1,1] hept-5-e -2,3-dicarboximidide, and-[2- (2-butoxyethoxy) ethoxy] -4,5-methylenedioxy-2-propyltoluene.
  • the pest control agent of the present invention may be used in any form.
  • a wettable powder, a wettable powder, a water solvent, an emulsion, a liquid, a suspension in water, and a milk in water may be added to the compound of the present invention by adding an agrochemical auxiliary.
  • It is used as a formulation in flowables such as suspending agents, capsules, powders, granules, aerosols, etc.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is arbitrary, but is usually selected from the range of 0.001 to 99.5% by weight in terms of the total amount of the active ingredients. It may be appropriately determined depending on the conditions.
  • wettable powders in the case of wettable powders, wettable powders, aqueous solvents, emulsions, liquids, flowables, capsules and the like, about 0.01 to 90% by weight, preferably 1 to 50% by weight
  • the pesticide adjuvants used are used for the purpose of improving pest repellent, controlling and controlling effects, and stabilizing and dispersing.
  • carriers diiluents
  • spreading agents spreading agents
  • emulsifiers emulsifiers
  • moisturizers emulsifiers
  • An extender, a dispersant, a disintegrant and the like can be used.
  • Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, and sulfoxides such as dimethylsulfoxide. , Methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like.
  • solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, Montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
  • Usable surfactants can be used as emulsifiers and dispersants, for example, higher alcohols such as sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkyl esters: polyester, lauryl betaine, etc.
  • Anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
  • a spreading agent such as polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl X diester; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; sodium lignin sulfonate Disintegrants such as sodium lauryl sulfate
  • a wettable powder the active ingredient is mixed with a compound of the general formula (I), a solid carrier, a surfactant and the like to produce a raw powder, and the raw powder is used at a predetermined concentration. Can be diluted with water and applied.
  • an undiluted emulsion can be prepared by mixing a solvent and a surfactant with the above compound of the active ingredient, and the undiluted solution can be diluted with water to a predetermined concentration before use. it can.
  • the compound of the active ingredient and the solid carrier can be mixed and applied as it is.
  • the compound of the active ingredient, the solid carrier and a surfactant are mixed and used. It can be manufactured by granulation and applied as it is.
  • the production method of each of the above-mentioned preparation forms is not limited to the above-mentioned one, and can be appropriately selected by those skilled in the art according to the kind of the active ingredient, the purpose of application, and the like.
  • the method of use depends on the type and amount of pests, the type of crops and trees, the type of cultivation, and the state of growth, but for arthropods, gastropods, nematodes, etc.
  • 0.1 to 1000 g, preferably 1 to, of active ingredients per 10 ares is applied to places where damage by these pests is occurring or where damage is expected to occur. do it.
  • Specific application methods include, for example, the aforementioned wettable powders, wettable powders for granules, aqueous solvents, emulsions, liquids, suspensions in water, and flowables such as emulsions in water, and capsules, etc., diluted with water. It can be applied to crops, trees, etc.
  • the preparations may be applied to crops, trees, etc. within the range of the use described above.
  • the target pest mainly infects crops, trees, etc. in the soil
  • Flowables, capsules, etc. may be diluted with water and applied generally in the range of 5 to 500 liters per 10 ares.
  • the medicine may be sprayed on the soil surface so as to be evenly distributed over the whole application area, or it may be irrigated into the soil.
  • the preparation is in the form of a powder or granules
  • the preparation may be sprayed as it is on the soil surface so as to be uniform over the entire area to be applied.
  • spraying or irrigation it may be applied only around seeds, crops, trees, etc. that you want to protect from damage by pests, or plowed during or after spraying to disperse the active ingredient mechanically. Good.
  • a pesticidal composition containing the compound of the present invention as an active ingredient may be adhered around plant seeds by a known method. Such treatment not only prevents damage by pests in the soil after sowing the seeds, but also protects the foliage, flowers, fruits, etc. of the plants from pest damage after growth. You can do it.
  • the pesticidal composition containing the compound of the present invention as an active ingredient may be used alone or with other active compounds such as insecticides, acaricides, nematicides, bactericides, repellents and synergists. Can be used in combination with or the like or as a mixture.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is optional. However, it is usually 0.0001 to 95% by weight of the total amount of active ingredients, 0.005 to 10% by weight for oils, powders, granules, etc., and 0.01 to 50% by weight for emulsions, wettable powders and sols. Preferably. Specifically, for example, if the combating-controlling termites Ya beetles, etc., the 0.01 ⁇ 100g as an active ingredient compound doses per lm 2 may be sprayed on the soil or wood surface.
  • the pesticidal composition containing the compound of the present invention as an active ingredient is parasitic on animals such as pets bred in the livestock industry, fisheries industry and at home, internally or externally. It is effective in repelling, exterminating and controlling pests such as arthropods, nematodes, flukes, tapeworms, protozoa, etc., which cause direct harm or damage by spreading diseases. Yes, it can be used to prevent and treat diseases related to these pests.
  • Target animals include vertebrates, for example, live-blooded vertebrates such as cattle, sheep, goats, horses, pigs, and other livestock and farmed fish; and poultry, dogs, cats, mice, rats, Rodents such as hamsters and squirrels; carnivores such as ferrets; and experimental animals such as fish and the like can be mentioned.
  • vertebrates for example, live-blooded vertebrates such as cattle, sheep, goats, horses, pigs, and other livestock and farmed fish
  • carnivores such as ferrets
  • experimental animals such as fish and the like can be mentioned.
  • dipterans examples include, but are not limited to, the Afidae family, such as Yamato-abu, Ammetgebu-bu, and Akausiab; the housefly family, such as the chrono, 'e, housefly, and the fly; the dipteromycetes, such as the maize fly; Dermatidae, such as Pterodactylidae, etc .; Dermatidae, such as Lepidoptera purpurea; Drosophilidae, such as Drosophila and Drosophila; Family; examples of the family include the brassicaceae, such as Shinukaka power and Nichinukaka power.
  • Afidae family such as Yamato-abu, Ammetgebu-bu, and Akausiab
  • the housefly family such as the chrono, 'e, housefly, and the fly
  • the dipteromycetes such as the maize fly
  • Dermatidae such as Pterodactylidae, etc
  • Laminariae examples include the flea family such as cat flea and flea flea.
  • Lobaceae lice such as lice of the night lice and white lice
  • Lepidoptera of the nits such as the lice of Maha lice
  • Lynfidae such as reed lice and the like.
  • Examples of the acarids of the arthropod spiders include the ticks of the spider mites, e.g., ticks and ticks, such as the ticks and mites; the ticks of the sick mites; the mites of the spider mites; the mites of the spiders; Family: Dermatophagoids such as Dermatophagoides farinae and Trichoderidae; and Dermatophagoids such as Dermatophagoides farinae and Dermatophagoides farinae.
  • the following can be illustrated as examples of the nematodes of the nematode phylum.
  • Examples of the order Coleoptera include caterpillars, pig nematodes, pig lungworms, hairy nematodes, caterpillars, and the like.
  • roundworm for example, roundworm, roundworm of chicken, etc. can be mentioned.
  • flatworm flukes examples include Schistosoma japonicum, Hepatic flukes, Desert flukes, Lesterum pestisman, and Japanese egg fluke.
  • tapeworms examples include foliate tapeworms, tapeworms, Beneden tapeworms, square tapeworms, striated tapeworms, and tapered tapeworms.
  • the protozoan phylum flagellates as the root flagellates, for example, Histomonas, etc.
  • the protoflagellate for example, Leishmania, Trypanosoma, etc.
  • the polyflagellate for example, Giardia, etc.
  • Trichomonas for example, Trichomonas.
  • the pesticidal composition containing the compound of the present invention as an active ingredient can be used alone or in combination with other active compounds such as insecticides in any of the above-mentioned preparations effective in the livestock and fisheries fields, and in any use form prepared by the preparation.
  • insecticides acaricides, nematicides, fungicides, synergists, plant conditioners, herbicides, baits and the like.
  • active compound include, but are not limited to, the substances exemplified in “(A) Agriculture, forestry scene, etc.”.
  • Specific methods of application include, for example, mixing with feed such as livestock and pets, Orally ingestible pharmaceutical compositions, such as tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated bait, controlled release containing pharmaceutically acceptable carriers and coating materials Orally administered as a large-sized pill, other sustained-release device kept in the gastrointestinal tract, or transdermal as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc. Can be given.
  • feed such as livestock and pets
  • Orally ingestible pharmaceutical compositions such as tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated bait, controlled release containing pharmaceutically acceptable carriers and coating materials
  • devices attached to animals to control arthropods can also be used.
  • devices attached to animals to control arthropods can also be used.
  • collars, medallions, jars, etc. can also be used.
  • capsules, pills or tablets containing a predetermined amount of the active ingredient are usually employed. These forms are used by uniformly mixing the active ingredient with a suitably comminuted diluent, filler, disintegrant and / or binder such as starch, lactose, talc, magnesium stearate, vegetable gum, and the like. Manufactured.
  • a suitably comminuted diluent, filler, disintegrant and / or binder such as starch, lactose, talc, magnesium stearate, vegetable gum, and the like.
  • the weight and content of the anthelmintic may be appropriately determined depending on the type of host animal to be treated, the degree of infection, the type of parasite, and the weight of the host.
  • the active ingredient compound When administered via feed, there may be mentioned, for example, a method in which the active ingredient compound is uniformly dispersed in the feed, a method in which the drug is used as a top dressing, or a method in which the drug is used as a pellet.
  • the final feed usually contains 0.0001 to 0.05% by weight, preferably 0.0005 to 0.01% by weight of the active ingredient compound.
  • a liquid carrier vehicle When dissolved or dispersed in a liquid carrier vehicle, it may be administered parenterally to animals by intraruminal, intramuscular, intratracheal or subcutaneous injection. Because of parenteral administration, the active compound is preferably mixed with vegetable oils such as peanut oil and cottonseed oil.
  • Such a formulation generally contains the active ingredient compound in an amount of 0.05 to 50% by weight, preferably 0.1 to 0.2% by weight.
  • a preparation mixed with a carrier such as dimethyl sulfoxide or a hydrocarbon-based solvent can be directly or locally administered to the external surface of a livestock animal by spraying or direct injection.
  • the pesticidal agent of the present invention has an adverse effect on pests in public health situations such as adversely affecting clothes, food and living environment, causing harm to the human body, and carrying and transmitting pathogens. It is also effective for avoidance, eradication and control for maintaining public health.
  • the pesticidal agent of the present invention includes, for example, wood products inside and outside the house itself, wood products such as wooden furniture, stored foods, clothing, books, animal products (skin, wool, wool, feathers, etc.).
  • arthropod phylum Insecta examples include the following.
  • Lepidoptera for example, Pterodaceae, such as Moncidae moth; Power, such as Kunugikarehaga; Rehagaceae, such as Aoiraga; Malagalaceae, such as evening croaker; etc .; Gibionidae such as moths;
  • the Coleoptera for example, the family Ceratopogonidae such as Akagamirimidoki; Tenebrionidae, such as Scots beetle; Lentinidae, such as Saw-throat and Lentinus; Lentinidae, such as tobacco and Jinsanshibushi; A family of beetles, such as Marcazobushimushi and Harajirokatsubushimushi; a family of beetles, such as Nisesema ruhibonboshi;
  • Hymenoptera include, for example, wasp family such as wasp, squirrel family such as octopus, and bee family such as beetle.
  • dipteran examples include dipteranaceae, such as japonicus, etc .; brassicaceae, such as brassicae; mussuriaceae, such as sesjusuri, etc .; buds, such as ashmadarabu, etc .; Rubiaceae; Mulberry fly, such as Mulberry fly; Mulberry engineering, such as Sentinia fly; Laceae, Musca domestica such as Drosophila melanogaster; Cheese fly, such as cheese fly.
  • dipteranaceae such as japonicus, etc .
  • brassicaceae such as brassicae
  • mussuriaceae such as sesjusuri, etc .
  • buds such as ashmadarabu, etc .
  • Rubiaceae such as Mulberry fly
  • Mulberry engineering such as Sentinia fly
  • Laceae Musca domestica such as Drosophila melanogaster
  • Cheese fly such as cheese fly.
  • Examples of the order Lepidoptera include a flea family such as a human flea.
  • As the order of the viscera there may be mentioned, for example, the order of the order Beetle, such as the beetle.
  • cockroaches include the cockroach family, such as the cockroach and the cockroach, and the cockroaches family such as the cockroach, the black cockroach, and the black cockroach.
  • the Orthoptera includes, for example, the family Corrugidae such as Madara Powered Horse and Powered Powered Horse.
  • louse examples include, but are not limited to, lice of the lice family such as lice of the lice;
  • bed bugs such as bed bugs
  • bugs such as green turtles
  • the termites of the termites such as the termites and termites; the termites of the termites such as the termites; the termites of the termites such as the termites; the termites of the termites such as the termites of the termites; Konakya evening family.
  • spots for example, spots such as stag beetles and sea stains may be mentioned. Can be.
  • arthropod spiders The following can be exemplified as arthropod spiders.
  • ticks such as Schulz ticks; Dermatophagoides such as house dust mites; Dermatidae such as Minamimite; Louse ticks such as lice mites; Dermatidae such as Dermatidae; Dermatidae such as Dermatophagoides; Oxodidae; Dermatidae, such as Akatsugamushi; Dermatidae, such as Dermatophagoides farinae and Dermatophagoides farinae; Sugar mites, such as sugar cane.
  • Dermatophagoides such as house dust mites
  • Dermatidae such as Minamimite
  • Louse ticks such as lice mites
  • Dermatidae such as Dermatidae
  • Dermatidae such as Dermatophagoides
  • Oxodidae Dermatidae
  • Dermatidae such as Akatsugamushi
  • Dermatidae such as Dermatophagoides farinae and Dermatophagoides farinae
  • Examples of the true arachnids include, for example, the spiders such as Birch spiders; the spiders such as ash spiders; the spiders such as staghorn spiders and the spider spiders; the spiders spiders such as hiratagmo; the spiders such as the spiders spiders. And the like.
  • scorpiones there may be mentioned, for example, the scorpion family, such as the scorpion.
  • examples of the order of the order Aphididae from the order of the order of the order of the order Aphididae include those of the family Aphididae, such as Tobism and Aoazukade, and examples of the order of the order Gastropoda include, for example, the family Dipteridae.
  • arthropod phylum, Ophiaceae examples include, for example, Rhododendrons such as toadscomb, and examples of the arthropod, such as Crustacea, include the pallidaceae, such as the pods.
  • examples of the annelid fauna, Lepidoptera include the Lamaviridae family such as the Lamavir.
  • the pesticidal composition of the present invention may be used alone or in the form of any other active compound such as an insecticide, acaricide, nematocide, in a formulation effective in the public health situation described above, and in any use form prepared by the formulation. It can be used in combination with or as an admixture with agents, fungicides, synergists, plant regulators, herbicides, baits and the like.
  • active compounds include:
  • the form of use of the pesticidal composition of the present invention is optional.
  • spray oils, emulsions, wettable powders, powders, etc. install resin vaporizers, treat smoke and aerosols, install granules, tablets and baits, and install aerosols. It can be controlled by spraying.
  • the amount of the active ingredient compound in these preparations is preferably 0.0001 to 95% by weight.
  • pests such as arthropods that cause direct harm or arthropods that are vectors for disease, etc.
  • they can be applied in other forms such as granules, tablets or poison bait, or by dripping floating powder, granules, etc. into waterways, wells, reservoirs, water tanks and other running or stationary water. do it.
  • formulations in these forms of use can also be present as mixtures with other active compounds as described above, for example with pesticides, acaricides, nematicides, fungicides, repellents or synergists.
  • these preparations contain the active ingredient compound in a total amount of 0.0001 to 95% by weight. Incidentally, it can be used in combination with other active compounds at the time of use.
  • the compounds of the present invention may be used alone or in combination with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents, synergists and the like, or as admixtures. Can be used.
  • the content of the active ingredient compound such as the compound of the present invention in these preparations is optional, but it is usually 0.0001 to 95% by weight in total of the active ingredient, and 0.005 to 10% for oils, powders, granules and the like. %, Preferably 0.01 to 50% by weight in emulsions, wettable powders, sols and the like. Specifically, for example, if the combating-controlling termites Ya beetles, etc., 0.01 to as active ingredient compound doses per lm 2: LOOG may be sprayed around or directly surface.
  • appropriate orally ingestible pharmaceutical preparations such as pharmaceuticals Tablets, pills, capsules, pastes, gels, beverages, medicated feed, medicated drinking water, medicated bait, sustained release large pills, and other pills containing an acceptable carrier or coating material to be retained in the gastrointestinal tract It can be administered orally as a sustained release device or the like, or transdermally as a spray, powder, grease, cream, ointment, emulsion, lotion, spot-on, pour-on, shampoo, etc.
  • N-chlorosuccinimide 0.27 was added to a mixture of 0.63 g (2.0 mmol) of 2,6-dichloro-4- (3,3-dichloro-2--2-propenyloxy) benzaldoxime, 3 ml of THF and 1 ml of DMF. g (2.0 mmol) was added, and the mixture was stirred at room temperature for 1 hour. A solution of 0.41 g (2.0 mmol) of 2- (aryloxy) -5-trifluoromethylpyridine and 0.20 g (2.0 mmol) of triethylamine in 2 ml of THF was added, and the mixture was further stirred for 16 hours.
  • the solvent was distilled off from the reaction mixture, and to the residue obtained, 50 ml of ethyl acetate was added, washed with water, saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate.
  • the solvent was distilled off from the reaction mixture, and to the residue obtained, 50 ml of ethyl acetate was added, and the mixture was washed with water, saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate.
  • a solution of 0.24 g (ll mmol) of 4- (4-trifluoromethylphenoxy) -1-butyne and 0.15 g (1.5 mmol) of triethylamine in 2 ml of THF was added, and the mixture was stirred at room temperature for 18 hours.
  • 2,6-Dic-mouth-4- (3,3-Dic-mouth propidinyl-1-oxy) benzaldoxime (0.47 g, 1.5 mmol) was added to THF (1.5 ml) and DMF (1.5 ml). After dissolution, TV-chlorosuccinic acid imide (0.24 g, 1.8 mmol) was added. After 1.5 hours, a solution of 4- (4-trifluoromethylphenoxy) phenoxypropyne (0.44 g, 1.5 mmol) and triethylamine (0.23 g, 2.3 mmol) in THF (3 ml) was added. After stirring for 19 hours, add water and add ether Extracted. After washing with saturated brine, drying over anhydrous sodium sulfate, filtration, concentration, and purification by medium pressure silica gel column chromatography, the title compound (0.62 g, l.Ommol, 68%) was obtained.
  • 2,6-Dichloro mouth-4- (3,3-dichloro-2-propenyloxy) benzaldoxyamidine (2.00 g, 6.06 mmol) was dissolved in THF (30 ml) and the mixture was cooled.
  • Sodium hydride (60% in mineral oil, 0.29 g, 7.3 mmol) was added, and the mixture was stirred at room temperature for 20 minutes and then at 60 ° C for 25 minutes. The mixture was allowed to cool to room temperature, and a solution of ethyl glycolate (1.26 g, 12.1 mmol) in THF (10 ml) was added dropwise.
  • the physical properties in the table indicate the refractive index for liquids, the melting point for solids, and the viscosity for those for which neither measurement was possible.
  • the compound of the present invention was added to 20 parts by weight of a mixed solvent consisting of 35 parts by weight of xylene and 30 parts by weight of dimethylformamide and dissolved.
  • a mixture with an ionic surfactant (Toho Chemical Co., Ltd., trade name) was added in an amount of 15 parts by weight to obtain an emulsion containing an active ingredient of 20% by weight.
  • Formulation Example-4 Flowable
  • Example 11 Cabbage cut leaves (6 cm in diameter) were immersed in a water dilution of the insecticide (wettable powder) of the present invention manufactured according to the formulation of Example 1 for 1 minute. After immersion, it was air-dried, placed in a plastic cup (7 cm inside diameter), and five 3rd instar larvae of the Japanese moth were released into this cup (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C, and after 4 days from the release, the larvae were examined for viability and agony, and the killing rate (%) was determined with 1/2 of the agony worms dead. The results are shown in Table 16.
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Test Example 1 2 Insecticidal effect on the larvae of Lotus spruce
  • Preparation Example-1 Cabbage cut leaves (diameter 6 cm) were immersed for 1 minute in a water dilution of the insecticide (wettable powder) of the present invention manufactured according to the formulation of Preparation Example 1. After immersion, it was air-dried, placed in a plastic cutlet (7 cm inside diameter), and five third-instar larvae of Spodoptera litura were released into this cup (1 concentration, 2 repetitions). They were kept in a constant temperature room at 25 ° C, and after the release of the insects, the larvae were examined for life and death and their agony. The results are shown in Table 17.
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Formulation Example 1 A solution (3.5 ml) obtained by diluting the acaricide (wettable powder) of the present invention prepared according to the formulation of 1 to a predetermined concentration with water was spread on the above-mentioned leaves using a rotary spray tower (Mizuho Rika Chemical Co., Ltd.). ) (1 concentration, 2 replicates). Twenty-four hours after the treatment, adults were examined for viability and the acaricidal rate (%) was determined. The results are shown in Table 18.
  • Test Example 1 4 Insecticidal effect on the larvae of Anemonium japonicus
  • Formulation Example 1 An artificial feed (Nippon Nosan Kogyo Co., Ltd.) cut into a water diluent of the insecticide (wettable powder) of the present invention manufactured in accordance with the prescription of 1 and having a diameter of about 5 cm x 1/8 yen and a thickness of 0.5 cm. Sector FL) for 10 seconds. After immersion, they were placed in a plastic cup (inner diameter 4 cm), and five third-instar larvae of the cynoid snail were released into the cup (1 concentration, 2 repetitions). The larvae were kept in a constant temperature room at 25 ° C, and after 5 days from the release, the larvae were examined for viability and agony. The results are shown in Table 19.
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • Compound concentration insecticidal rate Compound concentration insecticidal rate
  • the pesticidal composition containing the dihalopropene derivative of the present invention as an active ingredient is useful for pests in the fields of agricultural and horticultural use, clothing, eating and drinking, livestock and pets, and particularly harmful insects and mites in agricultural and horticultural activities. It has an extremely excellent controlling effect and is useful as a controlling agent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (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)
  • Pest Control & Pesticides (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des dérivés de dihalopropényloxybenzène représentés par la formule (I) qui sont très efficaces pour éliminer les parasites dans le domaine de l'agriculture, de l'horticulture, de la vie quotidienne, de l'élevage de bétail, des animaux de compagnie et autres (plus particulièrement les insectes nuisibles et les acariens dans les domaines de l'agriculture et de l'horticulture) et qui sont fortement inoffensifs pour les mammifères et les poissons. Dans la formule (I), A représente aryle, un hétérocycle, etc. ; W représente oxygène, soufre, etc. ; Q représente aryle, un hétérocycle, etc. ; R?1, R2, R3, R4, R5 et R6¿ représentent chacun hydrogène, alkyle, etc. ; ou R?1 et R2, R3 et R4, et R5 et R6¿ peuvent former ensemble alkylidène ou alkylènedioxy ; p, q et r représentent chacun un entier à condition que p+q+r ne soit pas supérieur à 9 ; X1 et X2 représentent chacun halogéno, alkyle, etc. ; Y représente halogéno, alkyle ou haloalkyle ; n représente un entier tel que 0, 1 ou 2 ; et Z représente halogéno.
PCT/JP2000/008870 1999-12-17 2000-12-14 Derives de dihalopropenyloxybenzene et pesticides contenant ces derniers en tant qu'ingredients actifs Ceased WO2001044154A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU20238/01A AU2023801A (en) 1999-12-17 2000-12-14 Dihalopropenyloxybenzene derivatives and pesticides containing the same as the active ingredient

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP11/359045 1999-12-17
JP35904599 1999-12-17
JP11/363517 1999-12-21
JP36351799 1999-12-21

Publications (1)

Publication Number Publication Date
WO2001044154A1 true WO2001044154A1 (fr) 2001-06-21

Family

ID=26580891

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/008870 Ceased WO2001044154A1 (fr) 1999-12-17 2000-12-14 Derives de dihalopropenyloxybenzene et pesticides contenant ces derniers en tant qu'ingredients actifs

Country Status (2)

Country Link
AU (1) AU2023801A (fr)
WO (1) WO2001044154A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056735A1 (fr) * 2002-12-23 2004-07-08 Syngenta Participations Ag Derives de 2,6-dihalo-4-(3,3-dichloro-allyloxy-benzylalcool aux proprietes insecticides et acaricides
US6790852B2 (en) 2002-04-18 2004-09-14 Hoffmann-La Roche Inc. 2-(2,6-dichlorophenyl)-diarylimidazoles
JP2006525335A (ja) * 2003-04-30 2006-11-09 エフ　エム　シー　コーポレーション 殺虫性（ジハロプロペニル）フェニルアルキル置換ジヒドロベンゾフラン及びジヒドロベンゾピラン誘導体
US7144889B2 (en) 2003-10-16 2006-12-05 Hoffman-La Roche Inc. Triarylimidazoles
JP2008545744A (ja) * 2005-06-02 2008-12-18 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト フェニルアルキル置換ヘテロアリール誘導体
US7504413B2 (en) 2004-05-06 2009-03-17 Cytokinetics, Inc. N-(4-(imidazo[1,2A]pyridin-YL)phenethyl)benzamide inhibitors of the mitotic kinesin CENP-E for treating certain cellular proliferation diseases
US7618981B2 (en) 2004-05-06 2009-11-17 Cytokinetics, Inc. Imidazopyridinyl-benzamide anti-cancer agents
US7795448B2 (en) 2004-05-06 2010-09-14 Cytokinetics, Incorporated Imidazoyl-benzamide anti-cancer agents

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004726A1 (fr) * 1993-08-04 1995-02-16 E.I. Du Pont De Nemours And Company Oxazolines et thiazolines arthropodicides
EP0648729A1 (fr) * 1993-10-19 1995-04-19 Sumitomo Chemical Company Limited Composés dihalopropènes, insecticides/acaricides les contenant comme agents actifs et composés intermédiaires pour usage dans leur production
WO1995032193A1 (fr) * 1994-05-24 1995-11-30 Bayer Aktiengesellschaft Thiadiazolines substituees servant d'herbicides
WO1996038408A1 (fr) * 1995-05-31 1996-12-05 Mitsubishi Chemical Corporation Procede de production de derives de n-methylmethoxyiminoacetamide et produits intermediaires de ces derives
JPH09194418A (ja) * 1996-01-18 1997-07-29 Sumitomo Chem Co Ltd ジハロプロペン化合物、その用途およびその製造中間体

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995004726A1 (fr) * 1993-08-04 1995-02-16 E.I. Du Pont De Nemours And Company Oxazolines et thiazolines arthropodicides
EP0648729A1 (fr) * 1993-10-19 1995-04-19 Sumitomo Chemical Company Limited Composés dihalopropènes, insecticides/acaricides les contenant comme agents actifs et composés intermédiaires pour usage dans leur production
WO1995032193A1 (fr) * 1994-05-24 1995-11-30 Bayer Aktiengesellschaft Thiadiazolines substituees servant d'herbicides
WO1996038408A1 (fr) * 1995-05-31 1996-12-05 Mitsubishi Chemical Corporation Procede de production de derives de n-methylmethoxyiminoacetamide et produits intermediaires de ces derives
JPH09194418A (ja) * 1996-01-18 1997-07-29 Sumitomo Chem Co Ltd ジハロプロペン化合物、その用途およびその製造中間体

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6790852B2 (en) 2002-04-18 2004-09-14 Hoffmann-La Roche Inc. 2-(2,6-dichlorophenyl)-diarylimidazoles
US6946471B2 (en) 2002-04-18 2005-09-20 Hoffmann-La Roche Inc. 2-(2,6-Dichlorophenyl)-Diarylimidazoles
WO2004056735A1 (fr) * 2002-12-23 2004-07-08 Syngenta Participations Ag Derives de 2,6-dihalo-4-(3,3-dichloro-allyloxy-benzylalcool aux proprietes insecticides et acaricides
US7671201B2 (en) 2003-04-30 2010-03-02 Fmc Corporation Phenyl substituted cyclic derivatives
US7585891B2 (en) 2003-04-30 2009-09-08 Fmc Corporation Pesticidal (dihalopropenyl)phenylalkyl substituted benzodioxolane and benzodioxole derivatives
EP1620421A4 (fr) * 2003-04-30 2007-10-31 Bayer Cropscience Ag Derives insecticides de dihydrobenzofurane et de dihydrobenzopyrane a substitution (dihalopropenyl)phenylalkyle
JP2006525335A (ja) * 2003-04-30 2006-11-09 エフ　エム　シー　コーポレーション 殺虫性（ジハロプロペニル）フェニルアルキル置換ジヒドロベンゾフラン及びジヒドロベンゾピラン誘導体
US7576224B2 (en) 2003-04-30 2009-08-18 Fmc Corporation Insecticidal (dihalopropenyl) phenylalkyl substituted dihydrobenzofuran and dihydrobenzopyran derivatives
US7144889B2 (en) 2003-10-16 2006-12-05 Hoffman-La Roche Inc. Triarylimidazoles
US7504413B2 (en) 2004-05-06 2009-03-17 Cytokinetics, Inc. N-(4-(imidazo[1,2A]pyridin-YL)phenethyl)benzamide inhibitors of the mitotic kinesin CENP-E for treating certain cellular proliferation diseases
US7618981B2 (en) 2004-05-06 2009-11-17 Cytokinetics, Inc. Imidazopyridinyl-benzamide anti-cancer agents
US7795448B2 (en) 2004-05-06 2010-09-14 Cytokinetics, Incorporated Imidazoyl-benzamide anti-cancer agents
US8163919B2 (en) 2004-05-06 2012-04-24 Cytokinetics, Incorporated Imidazopyridinyl benzamide mitotic kinesin inhibitors
US8207340B2 (en) 2004-05-06 2012-06-26 Cytokinetics, Incorporated Imidazopyridinyl benzamide mitotic kinesin inhibitors
US8772507B2 (en) 2004-05-06 2014-07-08 Cytokinetics, Inc. Imidazole-benzamide anti-cancer agents
JP2008545744A (ja) * 2005-06-02 2008-12-18 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト フェニルアルキル置換ヘテロアリール誘導体
EP1890694A4 (fr) * 2005-06-02 2010-10-27 Bayer Cropscience Ag Derives heteroaryle phenylalkyle substitues
US7582668B2 (en) 2005-11-09 2009-09-01 Cytokinetics, Incorporated Imidazoyl-benzamide anti-cancer agents

Also Published As

Publication number Publication date
AU2023801A (en) 2001-06-25

Similar Documents

Publication Publication Date Title
WO2001000614A1 (fr) Derives de pyrazole, leur procede de production et pesticides les contenant comme principe actif
CZ229999A3 (cs) 1-arylpyrazoly a jejich soli, způsob jejich výroby, pesticidní prostředky obsahující tyto sloučeniny jako účinné látky a způsob hubení škůdců
BRPI0707722A2 (pt) compostos, processo para a preparaÇço de compostos, composiÇço agrÍcola, uso de compostos, mÉtodos para combater fungos fitopatogÊnicos, para combater pestes artràpedes, para proteger culturas de ataque ou infestaÇço por pestes artràpedes, para proteger sementes da infestaÇço por pestes artràpedes e das raÍzes e rebentos de mudas da infestaÇço por pestes artràpodes, e para proteger materiais nço-vivos do ataque ou infestaÇço por pestes artràpedes, e, semente
JPH03118369A (ja) 殺虫剤としてのｎ―フェニルピラゾール誘導体
BG64128B1 (bg) 1-арил-3-иминопиразоли като пестициди
WO1995004724A1 (fr) Derive d'imidazole et son procede de production, et substance anti-nuisibles
WO1997037990A1 (fr) Pyrazoles et produits chimiques a usage agricole contenant ces composes comme ingredients actifs
WO2001044154A1 (fr) Derives de dihalopropenyloxybenzene et pesticides contenant ces derniers en tant qu'ingredients actifs
CZ410489A3 (cs) N-Fenylpyrazol-4-ylderiváty, insekticidní prostředky tyto látky obsahující a jejich použití k hubení hmyzu
JP4600620B2 (ja) ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及び製造中間体、それらの製造方法、並びにそれらを有効成分とする有害生物防除剤
BG51143A3 (bg) Пестицидно средство и метод за борба с вредители
JPH08217609A (ja) 殺虫、殺ダニ剤組成物
WO2017213137A1 (fr) Nouveau composé et produit chimique agricole/horticole l'utilisant comme ingrédient actif
JP4186182B2 (ja) ヒドラゾン誘導体を有効成分とする殺虫剤及び新規ヒドラゾン誘導体
JPWO2000029387A1 (ja) ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及び製造中間体、それらの製造方法、並びにそれらを有効成分とする有害生物防除剤
KR20080077650A (ko) 5-아미노-1-[2,6-디클로로-4-(트리플루오로메틸)페닐]-4-[(트리플루오로메틸)설피닐]-1ｈ-피라졸-ｓ-카르보니트릴의다형체 및 무정형
BG64813B1 (bg) Пестицидни 1-арилпиразоли
JP4742333B2 (ja) Ｎ−チアジアゾリルシクロプロパンカルボン酸アミド類およびこれを有効成分とする殺虫、殺ダニ剤
JP2005512969A (ja) 殺虫殺ダニ性３−置換ピラゾール類
JP2001240583A (ja) ジハロプロペニルオキシベンゼン誘導体及びこれを有効成分とする有害生物防除剤
JP4952870B2 (ja) ２−アニリノ−４（３ｈ）−ピリミジノン誘導体及びそれらを有効成分とする殺虫、殺ダニ剤
JP4640538B2 (ja) ピリダジノン類およびこれを有効成分とする有害生物防除剤
JP4587090B2 (ja) ピラゾール誘導体及びその製造方法、並びにこれを有効成分とする有害生物防除剤
JP4868103B2 (ja) ピラゾール誘導体及びこれを有効成分とする有害生物防除剤並びにその製造方法
JP4512928B2 (ja) Ｎ−チアジアゾリルシクロアルカンカルボン酸アミド類およびこれを有効成分とする殺虫、殺ダニ剤

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase