WO2000068196A1 - Dérivés de dihydropyrrole à substitution n - Google Patents

Dérivés de dihydropyrrole à substitution n Download PDF

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WO2000068196A1
WO2000068196A1 PCT/JP2000/002848 JP0002848W WO0068196A1 WO 2000068196 A1 WO2000068196 A1 WO 2000068196A1 JP 0002848 W JP0002848 W JP 0002848W WO 0068196 A1 WO0068196 A1 WO 0068196A1
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group
atom
substituted
alkyl
atoms
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PCT/JP2000/002848
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English (en)
Japanese (ja)
Inventor
Shigeru Mio
Mitsuru Ito
Reiji Ichinose
Hideshi Okui
Toshiaki Iwasaki
Seiichiro Kodama
Jun Iwabuchi
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Sankyo Company,Limited
Nippon Kayaku Co.,Ltd.
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Priority to AU43157/00A priority Critical patent/AU4315700A/en
Publication of WO2000068196A1 publication Critical patent/WO2000068196A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms

Definitions

  • the present invention relates to an N-substituted dihydroxypyrrole derivative, a salt thereof, an intermediate thereof, and an agricultural chemical containing the N-substituted dihydroxypyrrole derivative as an active ingredient.
  • 3-phenyl-1,5-dihydropyrrole-2-one derivatives have been disclosed in, for example, Japanese Patent Application Laid-Open No. Hei.
  • N-substituted 1-4-hydroxy-1,5-dihydropyrrole-12-one derivative having a directly bonded hetero atom there is no known N-substituted 1-4-hydroxy-1,5-dihydropyrrole-12-one derivative having a directly bonded hetero atom.
  • the present inventors have conducted intensive studies on dihydroxypyrrole derivatives. They have found that they have an extremely excellent insecticidal activity and that they have an excellent herbicidal activity against various weeds, and thus completed the present invention.
  • the present invention has conducted intensive studies on dihydroxypyrrole derivatives. They have found that they have an extremely excellent insecticidal activity and that they have an excellent herbicidal activity against various weeds, and thus completed the present invention.
  • R 1 is a hydrogen atom; 6 alkyl group "the alkyl group, one C 3 ⁇ C 7 cycloalkyl group, one phenyl group (said phenyl group is 1 or selected from the group consisting of halogen atom and C L ⁇ C 6 alkyl group May be substituted by 5 substituents), 1 or 2 Ce alkoxy groups (the alkoxy group may be substituted by 1 to 5 halogen atoms), 1 C 2 -C 6 Alkoxy group, one (C t Cg alkoxy) C 1 -C 6 alkoxy group, one benzyloxy group, one C i -C 6 alkylthio group, one to three halogen atoms, one A cyano group, one di (-alkyl) amino group or one 5- or 6-membered heterocyclic group ⁇ the complexed cyclic group contains 1 to 4 oxygen, sulfur, or nitrogen atoms and is a halogen atom; atoms and ⁇ 6
  • Le group is yo substituted by 1 to 3 halogen atoms,), C 2 -C 6 alkynyl Group, phenyl group (the phenyl group may be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom and a CLC 6 alkyl group), a 5- or 6-membered heterocyclic group ⁇ the heterocyclic group Contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms, and may be substituted by one to an alkyl group (the alkyl group may be substituted by one to three halogen atoms). Les ,. ⁇ , ⁇ .
  • alkylcarbonyl group (the alkylcarbonyl group may be substituted by 1 to 3 halogen atoms, 1 ⁇ to ⁇ alkoxy group or 1 fuunoxy group), a benzoyl group (the benzoyl group is Consists of a halogen atom and an alkyl group It may be substituted by 1 to 5 substituents selected from the group.
  • C 2 -C 8 alkoxy sikareboninole group di (C 1 -C 6 alkyl) -capable rubamoyl group, C 1 -C 6 alkylsulfoyl group or phenylsulfonyl group (the phenylsulfonyl group is a halogen atom and And may be substituted by 1 to 5 substituents selected from the group consisting of 6 alkyl groups.
  • R 2 and R 3 are the same or different and each represent a hydrogen atom, an alkyl group ⁇ the alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is A) substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, an ⁇ alkyl group and an alkoxy group.), One or two alkoxy groups, one (C 1 To C 6 alkoxy) CL Ce alkoxy group, 1 to 13 halogen atoms or 1 5 or 6 membered heterocyclic group (the heterocyclic group is 1 to 4 oxygen atoms, sulfur atom or nitrogen Containing an atom.
  • C 3 ⁇ C 7 cycloalkyl group C 2 -C 6 alkenyl group (said alkenyl group is optionally substituted by 1 to 3 halogen atoms.), C 2 ⁇ C 6 alkynyl group, Fuyuniru group ( those the phenyl group, a halogen atom, C t Ce alkyl group and ⁇ _ ⁇ .
  • 6 alkoxy force Les yo substituted by 1 to 5 substituents selected from Ranaru group.
  • 5 Moshiku is 6-membered heterocyclic group ⁇
  • the heterocyclic group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms, and is a halogen atom and a C i Ce alkyl group (the alkyl group is 1 to 3 halogen atoms ) Is substituted with one or two substituents selected from the group consisting of force.
  • R 2 and R 3 together with the carbon atom to which they are attached, are a 4- to 7-membered cycloalkane, cycloalkene or cycloalkanegen ring ⁇ wherein the ring is 1 to 3 alkyl groups, 1 C 1 -C 6 alkoxy group, 1 (C i Ce alkoxy) Ci Ce alkoxy group, 1 di (C i Ce alkyl) amino group, 1 C 1 -C 4 alkylenedioxy group or one N-(-alkoxy) imino group, and at any position, a ring is an oxygen atom, a sulfur atom or a group represented by the formula NR 6 (Wherein, R 6 represents an ⁇ ⁇ alkyl group.). ⁇ ,
  • R 4 is a hydrogen atom, C 2 -C 1 .
  • Alkyl carboxy group (the alkyl carboxy group is one to three halogen atoms, one C. to C 7 alkyl carbonyloxy group, Pieces It may be substituted by a alkoxy group or one phenoxy group. ), C 4 -C 7 cycloalkylcarbonyl group ⁇ the cycloalkylcarbol group is 1 to 4 substituents selected from the group consisting of an alkyl group and a halogen atom, 1 or 2 C 1 -C 6 alkoxy groups, 1 or 2 cyano groups or 1 phenyl group (the phenol The group may be substituted by one CLCS alkoxy group.
  • C 3 -C 7 alkenylcarbonyl group (said alkenyl group may be substituted by 1 to 3 halogen atoms.), Benzoiru group ⁇ said base Nzoiru group, a halogen atom and ⁇ Ce alkyl group (said The alkyl group may be substituted by 1 to 3 halogen atoms or 1 phenoxy group.) 1 to 5 substituents selected from the group consisting of: 1 to 3 to 1 to 6 alkoxy groups; C 2 -C 7 alkylcarbonyloxy, 1 C 2 -C 7 alkoxycarbonyl, 1 C i Ce alkylthio, 1 C t Ce alkylsulfinyl, 1 C 1- It may be substituted by a C 6 alkylsulfonyl group, one phenoxy group, one cyano group or one nitro group.
  • a 4- to 6-membered heterocyclic carbonyl group ⁇ the heterocyclic carbonyl group contains 1 to 4 oxygen, sulfur, or nitrogen atoms, and 1 to 3 ⁇ to ⁇ 6 alkyl groups (the alkyl The group may be substituted by 1 to 3 halogen atoms.), 1 to 3 C 1 -C 6 alkoxy groups, 1 C 1 -C 6 alkylthio group or 1 halogen atom And may be condensed with a benzene ring.
  • (Phenylthio) carbonyl group ⁇ the (phenylthio) carbonyl group is substituted by 1 to 5 substituents selected from the group consisting of a halogen atom and an ⁇ ⁇ alkyl group. May be replaced. ⁇ , (C 1 -C 6 alkoxy) thiocarbonyl group, (phenoxy) thiocarbonyl group (the (phenoxy) thiocarbonyl group is 1 to 5 carbon atoms selected from the group consisting of halogen atoms and d to C 6 alkyl groups.
  • A is a ⁇ Cs alkyl group (the alkyl group is substituted with 1 to 13 halogen atoms.), A halogen atom, a Ct Ce alkoxy group (the alkoxy group is 1 to 5 May be substituted by a halogen atom.), ⁇ ⁇ . 6 alkylthio group, A phenyl group (the phenyl group may be substituted by 1 to 5 substituents selected from the group consisting of a halogen atom and an alkyl group), a 5- or 6-membered heterocyclic group (the heterocyclic group is 1 to 4 oxygen Containing atoms, sulfur atoms or nitrogen atoms, halogen atoms and ⁇ ⁇ .
  • n an integer of 1 to 5
  • X represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group.
  • R 5 represents a hydrogen atom or an alkyl group.
  • ⁇ - ⁇ alkyl group is, for example, methyl, ethyl, propynole, isopropinole, butynole, isobutynole, sec-butynole, tert-butynole, pentynole, 1 to 6 carbon atoms such as 2-methylbutynole, 1-methylpentyl, neopentyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 3,3-dimethylinobutyl, 2,2-dimethylbutyl and 1,1-dimethylbutyl It is a linear or branched alkyl group, preferably a linear or branched alkyl group having 1 to 4 carbon atoms (to alkyl group), more preferably 1 to 3 carbon atoms. And more preferably a straight-chain or branched-chain alkyl group (-alkyl)
  • One or two alkyl groups (to alkyl groups), and particularly preferably a methynole group.
  • the “C 3 -C 7 cycloalkyl group” is, for example, a cycloalkyl group having 3 to 7 carbon atoms, such as cyclopropyl, cyclobutynole, cyclopentyl, cyclohexanol, and cycloheptyl.
  • An alkyl group preferably a cycloalkyl group having 3 to 6 carbon atoms (C 3 -C 6 cycloalkyl group), more preferably a cycloalkyl group having 5 or 6 carbon atoms.
  • the “halogen atom” is, for example, a chlorine atom, a fluorine atom, a bromine atom or an iodine atom, preferably a chlorine atom, a fluorine atom or a bromine atom, more preferably a chlorine atom or It is a fluorine atom, even more preferably a chlorine atom.
  • a phenyl group substituted by 1 to 5 substituents selected from the group consisting of a halogen atom and an alkyl group includes, for example, chlorophenyl, Triphenylenole, dichlorophenynole, diphnole olophenynole, chlorophlenolenophenyle, trichloride phenynole, triflenolenophenyl, pentafluorophenyl, methylphenyl, dimethylphenyl, trimethinole phenynole, tetramethinolephenyl , Such as ethyl phenyl, ethyl methyl phenyl, propyl phenyl, isopropyl phenyl, butyl phenyl, tert-butyl phenyl, pentino phenyl, hexyl phenyl, methyl phenyl and
  • ⁇ - ⁇ alkoxy group is, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy, 2-methylbutoxy, neopentoxy, 1 1 to 6 carbon atoms, such as -ethylpropoxy, hexyloxy, 1-methylpentoxy, 3,3-dimethylbutoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy and 2-ethylbutoxy
  • a linear or branched alkoxy group having 1 to 4 carbon atoms preferably an alkoxy group
  • more preferably a carbon number of 1 to 4 carbon atoms are preferably a carbon number of 1 to 4 carbon atoms.
  • ⁇ - ⁇ alkoxy group substituted by 1 to 5 halogen atoms includes, for example, chloromethoxy, 2-chloroethoxy, 3-chloropropoxy, 4-chlorobutoxy, 6_ Black hexinoleoxy, phnoreolomethoxy, diphnorelomethoxy, trifrenolemethoxy, 2-funoleoethoxy, 2,2,2-trichloroethoxy, 2,2,2-triphnoleethoxy, 1,1,2,2,2-ethoxy
  • halogen atoms such as 2-pentafluoroethoxy and fluorochloromethoxy, preferably the same or different
  • C 2 -C 6 alkenyloxy group includes, for example, buroxy, 2-Propenyloxy, 1-methyl-1-propenyloxy, 2-methynole 2-butene-noroxy, 2-buteninoleoxy, 3-methyl 2-butenoxy, 1-methyl-2-buteninoleoxy
  • a straight-chain or branched-chain Arukeniruokishi group (C 3 -C 6 Arukeniruokishi group), more preferably a carbon number of 3 to 5 straight-chain or branched-chain Arukeniruokishi group (C 3 -C 5 alkenyloxy group), and still more preferably, a linear or branched alkenyloxy group having 3 or 4 carbon atoms (C 3 -C 4 alkenyloxy group).
  • the “(CLCS alkoxy) C 1 -C 6 alkoxy group” is, for example, methoxymethoxy, methoxetoxy, methoxypropoxy, methoxybutoxy, methoxypentynoleoxy, methoxyhexoleoxy, ethoxymethoxy, ethoxy.
  • One of the foregoing such as ethoxy, ethoxypropoxy, isopropoxymethoxy, isopropoxymethoxy, tert-butoxymethoxy, tert-butoxychetoxy and hexyloxyhexyloxy;
  • the alkoxy group" is substituted by " ⁇ alkoxy” ⁇ ( ⁇ alkoxy) ⁇ ⁇ Ji 4 is an alkoxy group ⁇ , more preferably a the " ⁇ ⁇ 3 alkoxy group” is substituted " ⁇ ⁇ 3 alkoxy group” ⁇ ( ⁇ - alkoxy) - alkoxy group ⁇ , more preferably, the " ⁇ ⁇ Ji 2 alkoxy group” is said to have been replaced " ⁇ ⁇ 2 alkoxy group", still more preferably, main Tokishime butoxy group, Etokishime butoxy group, 2-main Tokishieto alkoxy group or a 2-Etokishetokishi group It is.
  • alkylthio group means, for example, methylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio, 2-methylbutylthio, 1-methylbutylthio, Straight or branched chain with 1 to 6 carbon atoms, such as methylpentinorethio, neopentylthio, hexylthio, 1-methylhexylthio, 3,3-dimethylbutylthio and 2,2-dimethylbutylthio
  • An alkylthio group preferably a linear or branched alkylthio group having 1 to 4 carbon atoms (to alkylthio group), more preferably Suitably, it is a straight-chain or branched-chain alkylthio group having 1 to 3 carbon atoms (up to 3
  • di ( ⁇ . 6 alkyl) amino group for example, Jimechirua amino group, such as Jechiruamino group, Jipuropiruamino group, diisopropyl ⁇ amino group, the jib Chiruamino groups and di Kishiruamino group
  • the " ⁇ A 6- alkyl group is an amino group having two bonds
  • the " ⁇ -alkyl group is an amino group ⁇ di (-alkyl) amino group ⁇ having two bonds
  • more preferably ⁇ -C 3 alkyl group '' is an amino group having two bonds
  • the ⁇ -C 2 alkyl group '' is an amino group having two bonds, and particularly preferably a dimethylamino group.
  • “5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms)” is, for example, a furyl, chenyl, pyrrolyl, pyrazolyl , Imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, tetrazolyl, oxaziazolyl, pyridyl, pyrimidinyl, pyrazur, pyridaziel, tetrahydrofuranyl, 1,3-dioxolanil, tetrahydranil, tetrahydranil, tetrahydranil A saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 4 oxygen, sulfur or nitrogen atoms in the ring, such as xanyl, pyrrolidyl, piperidyl and morpholy
  • a heterocyclic group and more preferably a pyridyl group, a chel group, a tetrahydrofuryl group or a dioxoral group as a substituent of the alkyl group of RR 2 and R 3 , and particularly preferably , a pyridyl group, a thienyl group or Jiokisoraniru group, most preferably a di Okisoraeru group, as R 1 or a, even more preferably, pyridyl group, Choi - group, in Tetorahi Dorofuraniru group or Jiokisoraeru group And particularly preferably a pyridyl group, a thienyl group or a dioxolar group, most preferably a pyridyl group or a thienyl group, and even more preferably as a group contained in R 4.
  • one oxygen It is a 5- or 6-membered heterocyclic group containing an atom or a nitrogen atom, particularly preferably a pyridyl group, a cyenyl group or a tetrahydrofuranyl group, and most preferably a tetrahydrofuranyl group.
  • a ⁇ Ce alkyl group substituted by 1 to 3 halogen atoms includes, for example, chloromethinole, bromomethyl, fluoromethyl, trifluoromethylinole, eodomethinole, chloroethinole, trifinolelotinole, cloguchipropinole, And the same or different 1 to 3 of the above-mentioned "halogen atoms" are substituted with the above-mentioned "-alkyl group", such as tert-butyl, pentyl and hexyl, preferably 1 to The above-mentioned FCLC 4 alkyl group substituted by three chlorine atoms, fluorine atoms or bromine atoms '', and more preferably, the above-mentioned ⁇ -alkyl group '' substituted by one to three chlorine atoms or fluorine atoms. .
  • Oite, androgenic atom to "and ⁇ ⁇ 6 alkyl group (the alkyl group may. Which is substituted by 1 to 3 halogen atoms) 1 or 2 selected from the group consisting of
  • a 5- or 6-membered heterocyclic group substituted by a substituent of ⁇ is, for example, chloropyridinole, Dioxolael, Fluoropyridinole, Phenoleo-Chenyl, Fluorodioxolael, Difluoropyridyl, Difluo, Phytoxorinole, Bromopyridinole, Bromocenyl, Promodioxorainole, Dibromopyridyl, Eodopyridyl, Methylpyridyl, Dimethylpyridyl, Dimethylpyridyl Pyridyl, isopropyl pyridi Butylpyridyl, tert-buty
  • substitutions chlorine atom, full Tsu atom, a bromine atom, the " ⁇ ⁇ 0 4 alkyl group” and “1 to 3 chlorine atoms, a fluorine atom or a bromine atom Selected from the group consisting of CC 4 alkyl group "that was A saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 3 oxygen atoms or nitrogen atoms in a ring, which is substituted with one or two same or different substituents; More preferably, the same or selected from the group consisting of chlorine atom, fluorine atom, the above-mentioned ⁇ -alkyl group '' and ⁇ C t Cs alkyl group substituted by 1 to 3 chlorine atoms or fluorine atoms '' A ⁇ saturated or unsaturated 5- or 6-membered heterocyclic group containing one or two oxygen or nitrogen atoms in the ring '' substituted with one or two different substituents, and even more preferably A pyr
  • R 1 of the present invention “1 C 3 -C 7 cycloalkyl group, 1 phenyl group (the phenyl group is 1 to 5 substituents selected from the group consisting of a halogen atom and an alkyl group) . which may be substituted by a group), one or two ⁇ - alkoxy group (said alkoxy group may be substituted by 1 to 5 halogen atoms), one C 2 -C 6 Aruke -.
  • Ruokishi group one (C 1 -C 6 alkoxy) C 1 -C 6 an alkoxy group, one Benjiruokishi group, one C 1 -C 6 alkylthio group, 1 to 3 C androgenic atom, one A cyano group, a di (C i Ce alkyl) amino group or a 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 4 oxygen, sulfur or nitrogen atoms) , 1 or 2 substituents selected from the group consisting of Nono androgenic atoms and CC 6 alkyl group
  • the alkyl group substituted by) is, for example, a cyclopropylmethyl, cyclohexylmethyl, cyclohexyl butynole, benzinole, (4-chloropheninole) methinole, or (4-methinolephene-norre)
  • Methinole pheninolebutinole, methoxymethyl, eth
  • the 6 membered heterocyclic group "is substituted is" ⁇ alkyl group ", the good applicable, one of the" C 3 -C 7 cycloalkyl group ", one phenyl group, one of the" salt atom, a fluorine atom, a bromine atom and ⁇ .
  • One Benjiruokishi group one of the r C t C alkylthio group ", 1 to 3 chlorine atoms, fluorine atom or bromine atom, one Shiano group, one of the" di (C t -C 4 Alkyl) amino group ”and one“ 5- or 6-membered heterocyclic group (the heterocyclic group is
  • C 2 -C 6 alkenyl group includes, for example, butyl, 2-chlorobi
  • Straight or branched chain with 2 to 6 carbon atoms such as 1-methynole_2_butynole, 3_butynole, 1-pentenole, 2_pentenyl, 1-hexenyl and 5-hexenyl
  • a straight-chain or branched-chain alkyl group having 3 to 5 carbon atoms C 3 -C 5 alkyl group.
  • Examples of the “-nore group” include, for example, 3 chloro-2-propenyl, 3,3-dichloro-2-propininole, 3-funoleol-2-propininole, 3,3-difuzoleone 2-prodinole 1 to 3 identical or different, such as ninole, 4,4-dichloro-1-3-buteninole, 5,5-diclo-1,4-pentenole and 4,5,5-trifluoro-4-pentyl Pieces of said
  • the above-mentioned ⁇ C 2 C 6 alkenyl group '' substituted by ⁇ halogen atom '' is preferably the same or different, wherein the same or different 1 to 3 chlorine atoms, fluorine atoms or bromine atoms are substituted
  • C 2 C 6 alkyl group refers to a carbon atom such as, for example, ethur, 2-propinole, 1-methylprobyl, 2-butynyl, 2-pentiel, 2-bexyl and 5-xynyl.
  • the number is 2 to 6 straight-chain or branched-chain alkynyl group, preferably a linear or branched alkynyl group having from 3 to 5 carbon (C 3 C 5 7 Rukiniru group), more preferably Is a linear or branched alkynyl group having 3 or 4 carbon atoms (C 3 C 4 alkynyl group), and more preferably a 2-propynyl group.
  • a 5- or 6-membered heterocyclic group substituted by one C 1 C 6 alkyl group (the alkyl group may be substituted by 1 to 3 halogen atoms.)
  • alkylcarbonyl group includes, for example, acetyl, propyl pioninole, propynolecarbonyl, isopropylcarbonyl, butylcarbonyl, sec-butynolecarbonyl, isobutylcanoleboninole, tert-butylcarbonyl, 1 to 1 carbon atoms, such as pentinole, pentyl-1-carbonyl, 2,2-dimethyl-11-propylcarbonyl, hexylcarbonyl, heptinolecarboel, octylcarbonyl and nonylcarboel
  • a carbonyl group to which a straight-chain or branched-chain alkyl group having 9 carbon atoms is bonded preferably a carbonyl group having a straight-chain or branched-chain alkyl group having 1 to 7 carbon atoms (C 2 -C 8 alkyl Cal Poni Le group), more
  • (C 2 -C 5 alkylcarbonyl group) particularly preferably a 2,2-dimethylpropionyl group, a 2,2-dimethylbutyryl group, a 3,3-dimethylbutyryl group or an acetyl group. is there.
  • Alkylcarbonyl group is, for example, methoxyacetyl , Ethoxyacetyl, isopropoxyacetyl, phenoxyacetyl, 3-phenoxypropiole, chloroacetyl, trichloroacetyl, trifluoroacetyl, 3-chloropropioel, 2,2-dimethylino-3-chloro 1 to 3 identical or different “halogen atoms”, 1 identical r ⁇ Ce alkoxy group, or 1 identical or different, such as propionyl, 2-chloro-2-methinolepropionyl and 2-methoxynonyl
  • ⁇ to alkylcarbonyl group substituted by a phenoxy group, preferably 1 to 3 identical or different chlorine atoms, Or bromine atom, it
  • ⁇ a benzoyl group substituted by 1 to 5 halogen atoms or one C 1 to C 6 alkyl group '' is, for example, chlorobenzoyl, dichlorobenzoyl, trichlorobenzoyl, Benzoyl, Funofole, Benzoinole, Trifole, Benzore, Trifole
  • 1 to 5 of the above-mentioned "halogen atoms" or one of the above-mentioned " ⁇ to 6 alkyl groups such as isopropyl benzoyl, butyl benzoyl, tert-butyl benzoyl, pentyl benzoyl and hexyl benzoyl
  • Is a bonded benzoyl group preferably the same or A different one to three chlorine atoms, a fluorine atom or a bromine atom, or one benzoyl group to which the above-mentioned ⁇ -
  • the “C 2 -C 8 alkoxycarbonyl group” is, for example, methoxy carbonyl nonole, ethoxy carbonyl, propoxy carbonyl, butoxy carbonyl, sec-butoxy carbonyl, isobutoxy carbonyl, cyclobutoxy, etc.
  • C 2 -C 5 alkoxycarbonyl group and more preferably, a carbonyl group (C 2 -C 4 alkoxy carbonyl group) in which a straight-chain or branched-chain alkoxy group having 1 to 3 carbon atoms is bonded. And further more preferably, a carboxyl group (C 2 -C 3 alkoxycarbonyl group) to which an alkoxy group having 1 or 2 carbon atoms is bonded. Is a methoxycarbonyl group.
  • the “di (C i Ce alkyl) caproluvyl group” is, for example, a dimethylaminocarbonyl group, a dimethylaminocarbonyl group, a dipropylaminocarbonyl group, a diisopropylaminocarbonyl group, a dibutylaminocarbonyl group.
  • Two identical or different “C 1 -C 6 alkyl” such as a carbonyl group and a dihexylaminocarbonyl group are a radical group bonded to a nitrogen atom, and are preferably the same or different.
  • the ⁇ FCLSCS alkylsulfonyl group '' includes, for example, methylsulfonyl, ethynolesnorhenol, isopropizolezolefoninole, propynolesnorrenhonyl, pentinolesulfonyl, pentylsulfonyl and hexylsulfonyl
  • a phenylsulfonyl group substituted by 1 to 5 halogen atoms or one ⁇ -alkyl group means, for example, phenylphenylsulfonyl, dichlorophenylenolesnolehoninole, trichlorophenyl Ninores Nolehoninole, Fuzoreno Feninole Snorehoninore, Diphnoleolopheninolesnorehoninore, Trifnoleolofeninolenolehoninole, Pentafuzoleno mouth Phenylsulfonyl, Bromophenyl Sulfonyl, Edophene-nore Snorlefonole Olofenis Lesnolehoninole, Methinolefenenolesnolehoninole, Etinolefeninolesnolehoninole, Propy
  • fluorine or bromine atom or one of the phenylalanine sulfonyl group " ⁇ ⁇ 4 alkyl group” is substitution, and more Preferably, they are the same or different 1 to 3 chlorine or fluorine atoms or a phenylsulfonyl group substituted by the above-mentioned ⁇ -alkyl group '', and still more preferably, the same or different 1 or 2 Is a phenylsulfoninole group substituted by a chlorine atom or a fluorine atom, or the above-mentioned “ ⁇ to 2 alkyl group”.
  • the groups are, for example, black fenole, fenoleolopheninole, bromophenole, odofenore, dichlorofeneole, diphneoleofe-nole, chlorophneolenofe-nore, triclope fenenore, trifnole , No ⁇ 0 —Funoleolofeninole, Methinole Feinore, Dimethinolefenore, Trimethinolefenore, Tetramethylenofe-Nore, Ethylphenyl, Ethylmethylphenyl, Propinolephenyl, Isopropinolefenole, Butinole Nin
  • R 2 and R 3 of the present invention “one C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is a halogen atom, ⁇ ⁇ .
  • 6 alkyl group and ⁇ ⁇ alkoxy group May be substituted with 1 to 5 substituents selected from the group consisting of), 1 or 2 ⁇ to 6 alkoxy groups, 1 (to anoreoxy) to anoreoxy group, and 1 to 13 C 1 -C 6 substituted by a halogen atom or one 5- or 6-membered heterocyclic group (the complex ring group contains 1 to 4 oxygen, sulfur or nitrogen atoms).
  • Alkyl group includes, for example, cyclopropylmethyl, cyclopropylethylenole, cyclohexynolemethinole, benzyl, 1-phenylenetinole, 1-phenylinolepropynole, 2-phenylenoletinole, 4-phenylenoletinolate, 4-phenylenoletinolate, Nginore, Bromobenzinole, phnoleo benzonole, dichlorobenzinole, diphnoleo benzonole, no.
  • alkoxy groups '' the same or different, from 1 to 5 chlorine atoms, fluorine atoms or bromine atoms, or one saturated or unsaturated ring containing 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms in a ring.
  • the “mono (-alkyl) amino group” includes, for example, the above-mentioned “- ⁇ ” such as a monomethylamino group, a monoethylamino group, a monopropylamino group, a monoisopropylamino group, a monobutylamino group and a monohexylamino group.
  • a ⁇ alkyl group is one bonded to an amino group, preferably a said” ⁇ 4 amino group alkyl group "is bonded one ⁇ mono ( ⁇ alkyl) amino group ⁇ , more preferably the a ' ⁇ Ji 3 alkyl group "amino group which is bonded one, even more preferably more, an amino group wherein" ⁇ - ⁇ alkyl group "is bonded one, particularly preferred, Monomechirua It is a mino group.
  • a “4- to 7-membered cycloalkane, cycloalkene or cycloalkanegen ring ⁇ wherein the ring is an oxygen atom, a sulfur atom or a group represented by the formula NR 6 at any position, , R 6 represents a CLCS alkyl group.)
  • Is for example, cyclobutane, cyclopentane, cyclohexane, cycloheptane, tetrahydrofuran, tetrahydropyran, tetrahydrothiopyran, N— Methynoreviperazine, cyclohexene, cyclopentene, oxolane, 1,3-dioxolane, 1,3-dithiolane, and 5,6-dihydro-4H— [1,3]
  • a 4- to 7-membered cycloalkane, cycloalkene or cycloalkanegen ring such as
  • a 4- to 6-membered cycloalkane, cycloalkene or cycloalkanegen ring wherein the ring is represented at any position by an oxygen atom, a sulfur atom or a formula NR 6 Wherein R 6 represents an alkyl group.
  • R 6 represents an alkyl group.
  • the ⁇ C 1 C 4 alkylenedioxy group '' is a straight-chain having 1 to 4 carbon atoms such as a methylenedioxy, ethylenedioxy, trimethylenedioxy or tetramethylenedioxy group. It is an alkylenedioxy group, preferably a methylenedioxy group, an ethylenedioxy group or a trimethylenedioxy group, more preferably an ethylenedioxy group or a trimethylenedioxy group.
  • the “N-( ⁇ alkoxy) imino group” is, for example, N-methoxyimino, N-ethoxyimino, N-propoxyimino, Nfsopropoxyimino, N-butoxyimino, N-pentynoleoxyimino.
  • the above-mentioned “-alkoxy group” is an imino group bonded to a nitrogen atom, such as an N-xysiloximino group, and preferably, the above-mentioned “ ⁇ -alkoxy group” is an imino group (N-( ⁇ ⁇ 4 alkoxy) imino group ⁇ , more preferably a the " ⁇ 3 Anorekokishi group” bonded to the nitrogen atom is imino group ⁇ N- (CL CS alkoxy) imino amino group ⁇ , suitably even more Is an imino group ⁇ N— (CL CS alkoxy) imino group ⁇ in which the above “ ⁇ alkoxy group” is bonded to a nitrogen atom.
  • “1 to 3 C 1 C 6 alkyl groups, 1 C 1 C 6 alkoxy group, 1 (C 1 C 6 alkoxy) C 1 C 6 alkoxy group, 4- to 7-membered cycloalkyl substituted by one di (C 1 C 6 alkyl) amino group, one C 1 C 4 alkylenedioxy group or one N— (CL CS alkoxy) imino group A can, cycloalkene or cycloalkanegen ring ”is, for example, 3-methyl Cyclopentane, 3-Methoxycyclopentane, 3,4-Dimethinolecyclopentane, 2-Methynolecyclohexane, 3-Methynolecyclohexane, 4-Methylcyclohexane, 3,5-Dimethy / lecyclohexane, 4 _ Ethyl ⁇ cyclohexane, 4-propynolecyclohexan
  • C 2 -C 7 alkylcarbonyloxy group includes, for example, acetyloxy, propionyloxy, propylcarbonyloxy, isopropylcarboxyoxylenoyl, butylcarbonyloxy, sec-butylcarbonyloxy, isobutyro Such as tinolecanolevonyloxy, tert-butylcarbonyloxy, pentylcarboxyloxy, pentinole-2-carbonyloxy, 2,2-dimethinole-1-propylcarboxyloxy and hexylcarbonyloxy, A carbonyloxy group to which a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms is bonded, preferably a straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms is bonded.
  • Carbonyloxy group (C 2 -C 5 alkylcarboxy group), more preferably 1 carbon atom And a carbonyloxy group (C 2 -C 4 alkylcarbonyloxy group) to which a linear or branched alkyl group of 1 to 3 is bonded, and even more preferably an acetyloxy group.
  • R 4 of the present invention "1 to 3 halogen atoms, one C 2 -C 7 alkyl force Ruboninoreokishi group, one CLCS alkoxy group or one C 2 is substitution by phenoxy group -C
  • the ⁇ 10 alkylcarbonyl group '' includes, for example, chloropropionyl, methylenolchloropropiol, dimethyl-chloropropionel, dimethylacetoxypropioninole, methoxyacetyl, ethoxyacetyl, methyl-1-methoxypropionyl, methyl one ethoxy-propionyl, such as methyl Ichime Tokishibutanoiru and Fuenoki Shiasechiru, the same or different 1 to 3 of the "halogen atom", one of the "c 2 to c 7 alkylcarbonyl O alkoxy group", one The above A "xy group” or the above-mentioned " ⁇ -.
  • Alkylcarbonyl group substituted by one phenoxy group, preferably 1 to 3 identical or different chlorine, fluorine or bromine atoms
  • the ⁇ C 4 -C 7 cycloalkylcarbonyl group '' includes, for example, cyclopropynolecarbonole, cyclobutylcanolebol, cyclopentylcanolebonyl, cyclohexylcarbonyl, cycloheptylcarbonyl, etc.
  • a phenyl group substituted by one C 1 -C 6 alkoxy group is, for example, methoxyphenyl, ethoxyphenyl, propoxyphenyl, It is a fuel group to which one of the above-mentioned ⁇ C 1 -C 6 alkoxy groups '' is bonded, such as isopropoxy phenol, butoxy phenol, pentoxy phenol and hexyl oxy phenol, and is preferably A phenyl group to which one of the above-mentioned ⁇ -alkoxy groups '' is bonded, more preferably a phenyl group to which one of the above-mentioned r C t C g alkoxy groups is bonded, and even more preferably And an ethoxyphenyl group.
  • R 4 of the present invention “1 to 4 substituents selected from the group consisting of an alkyl group and a halogen atom, 1 or 2 Ci Ce alkoxy groups, 1 or 2 cyano groups or A C 4 -C 7 cycloalkylcarbonyl group substituted by one phenyl group (the phenyl group may be substituted by one C 1 -C 6 alkoxy group) is, for example, methyl Cyclopropanecarbonyl, dimethylcyclopropanecarbonyl, trimethylcyclopropanecarbonyl, tetramethylcyclopropanecarbonyl, methyldichlorocyclopropanecarbonyl, cyanocyclopropanecarbonate, pheninolecyclopropanecarbonate, (ethoxyphene Nore) cyclopropane calboninole, (ethoxyphenole) dichlorocyclopropane canolebonino Les, Met / Recyclo Pentane Kano levo Nin
  • C 3 -C 7 alkenylcarbonyl group includes, for example, acryloyl, 2-butenoyl, methylatariloyl, 3-butenoyl, 2 pentenoyl, 4-pentenoyl, 2-methyl-2-butenyl, 3 Has 2 to 6 carbon atoms, such as —methyl-1-butenoyl, 1-cyclohexenecarbonyl, 1 ⁇ cyclopentenecarbonyl, 2-hexenoyl, 5_hexenoyl, 1-heptenoyl and 6-heptenoyl
  • a carbonyl group to which a linear or branched alkenyl group is bonded preferably a carbonyl group to which a linear or branched alkenyl group having 2 to 5 carbon atoms (C 3 -C 6 alkenyl) Carbonyl group), and more preferably a carbonyl group (C 3 -C 5 alkenyl alkenyl group) having
  • the ⁇ C 3 -C 7 alkenyl alkanol group substituted by 1 to 3 halogen atoms '' is, for example, chloroacryloyl, dichloroacryloyl, trichloroatarylonole, bromoatarylonole,
  • a Luke Lupo group preferably a said the same or different 1 to 3 chlorine atoms, a fluorine atom or a bromine atom is substituted" C 3 -C 6 alkenylcarbonyl group ", Ri preferably, the same or different 1 or 2 chlorine atoms or pre Symbol fluorine atom-substituted "C 3 -C 5 alkenyl group", preferably even more Is a C 3 -C 4 alkenylcarbonyl group substituted by one or two chlorine atoms.
  • "1 to 3 ⁇ 6 alkyl group is a halogen atom or substituted by one phenoxy group
  • a halogen atom or substituted by one phenoxy group for example, Monofu Noreoromechinore, Ziv Honoré Oro methylcarbamoyl Honoré , Trinoleolomethinolle, Black mouth diphnoleolomethinole, Trinoleoloechinole, phenoxymethinole, fenoxheti / re, phenoxypropizole, phenoxybutyl, phenoxypentyl and phenoxyhexyl
  • 1 to 3 "halogen atoms" or the above " ⁇ to 6 alkyl groups” substituted by one phenoxy group preferably the same or different 1 to 3
  • ⁇ -. 4 alkyl group more preferably, the above-mentioned "-alkyl group” substituted by the same or different 1 to 3 chlorine atoms or fluorine atoms or 1 phenoxy group, Even more preferably, it is a trifluoromethyl or phenoxymethyl group.
  • rC i Ce alkylsulfiel group is, for example, methylsulfinoleno, ethinoresnorefinole, propinoresnorefiele, isopropylsulfinole, petitnoresnorefine-nore, tert-butino
  • R 4 of the present invention 1 selected from the group consisting of “halogen atom and ⁇ to 6 alkyl group (the alkyl group may be substituted by 1 to 3 halogen atoms or 1 phenoxy group)” to 5 substituents, 1 to 3-alkoxy group, one C 2 -C 7 alkylcarbonyl O alkoxy group, one C 2 -C 7 alkoxycarbonyl two group, one C 1 - C 6 alkylthio group, one C 1 -C 6 alkyl sulfide El group, substituted by one C 1 -C 6 alkylsulfonyl group, one phenoxy group, one Shiano group or one nitro group
  • the benzoyl group include, but are not limited to, chlorobenzoyl, dichlorobenzoyl, triclobenzoyl, methynolebenzoyl, dimethylolbenzoyl, trimethinobenzoyl, methoxybenzoyl, dimethylbenzo
  • a “4- to 6-membered heterocyclic carbonyl group (the heterocyclic carboel group contains 1 to 4 oxygen atoms, sulfur atoms or nitrogen atoms, and may be bonded to a benzene ring.)
  • J represents, for example, chromancanoleboninole, benzodioxolecarbonyl, pyridincarbonyl, pyrimidinecarbonyl, pyrazinecarbyl, pyridazinecarboninole, pyrazolecarbol, thiazonolecarbonyl, oxazolecarbonyl, isoxanolcarbonyl 1 to 4 in the ring, such as oxazonorecanoleboninole, thiadiazonorecanolebonil, oxetanecarbonyl, N-monorephorin canoleponinole, tetrahydrofurancarbonyl and tetrahydroviranecarbonyl
  • a carbonyl group to which a 6- or 6-membered saturated or unsaturated heterocyclic ring is bonded preferably containing 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms in the ring, and condensed with a benzene ring Good, 4 to 6 membered saturated or unsaturated
  • a carbonyl group to which a heterocyclic ring is bonded more preferably benzodioxolecarbonyl, pyridinecarbonyl, N-morpholinecarbonyl, oxetanecarbon, pyrazolecarbonyl, thiadiazolecarbonyl, pyrimidinecarbonyl or chromancanoleboninole. Group.
  • “1 to 3 alkyl groups (the alkyl groups may be substituted with 1 to 3 halogen atoms)”, 1 to 3 alkyl groups, 1 to 6 alkoxy groups, ⁇ ⁇ Ji 6 alkylthio group or one 4-6 membered heterocyclic Karuboeru group substituted by halogen atom” for example, methyl pyridinecarboxamide - le, Mechirubi Li spermidine carbonyl, triflumizole Ruo Russia methyl pyridinecarboxylate - le, methyl 1-thiomethylpyrimidinecarbonyl, thiomethyl-1-trifluoromethylpyrimidinecarbonyl, dimethinolepyrazolecanolebonyl, methyl-1-trifluoromethylpyrazolcarbonyl, methylthiazolecarbonyl, methylthiaziazolecarbonyl, methyloxetanecarbon and Identical or different, such as methyltetrahydrofurancarbol And 1 to 3 of the "
  • C 1 -C 3 alkoxy group one of the " ⁇ alkylthio group” or one salt
  • a benzodioxonocarbonyl, pyridinecarbonyl, N-morpholinecarbonyl, oxetanecarbonyl, pyrazolecarbonyl, thiadiazolecarbonyl, pyrimidine canoleponinole or chroman force / repoenol group to which an atom or a fluorine atom is bonded.
  • the “5- or 6-membered heterocyclic group substituted by one or two substituents selected from the group consisting of a halogen atom and a ⁇ -. 6 alkyl group” is, for example, chlorovirazolyl , Methylpyrazolyl, Dimethylvirazolyl, Black Methylinopyrazolinole, Black Mouth Pyridyl, Fluoropyridinole, Methylpyridyl, Chlorpyrimidinyl, Methylpyrimidinyl, Methyltetrahydrofuranyl, Methyltetrahydroviranol-Methyldi
  • the same or different ones selected from the group consisting of the above-mentioned “no, halogen atom” and the above-mentioned “CC 6 alkyl group” such as Or the above "5- or 6-membered heterocyclic group substituted by two substituents (the heterocyclic group is
  • R 4 of the present invention “1 to 3 halogen atoms, 1 C 1 to C 6 alkoxy group, 1 CL Ce alkylthio group, 1 phenyl group (the phenyl group is a nitrogen atom 1 to 5 substituents selected from the group consisting of C i ⁇ C 6 alkyl group It has been replaced.
  • one 5 or 6-membered Hajime Tamaki (said heterocyclic group is 1 ⁇ optimum 4 oxygen atoms, a sulfur atom or a nitrogen atom, a halogen atom and C 1 -C 6 7 alkyl group A C 2 -C 8 alkoxycarbonyl group substituted by 1) or 2) substituents selected from the group consisting of, for example, 2-methoxyethoxycanoleponyl, 2-isopropoxyethoxycarbonyl, 2 —Phenoxhetoxycyanoleboninole, 2-methylthioethoxycarbonyl, 2-tetrahydrofuranylmethoxycarbonyl, 3-chloro-2,2-dimethylpropoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, 2,2,2-trifluoroethoxycarbo two Le, such as the same or different 1 to 3 of the "Nono Rogeshi atom", one of the "C 1 -C 6 alkoxy group , 1 ⁇ C 1
  • Saturated or unsaturated 5- or 6-membered heterocyclic group '' or one ⁇ one or the same or different one selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C 1 -C 4 alkyl group The above-mentioned ⁇ C 2 -C 6 -substituted saturated or unsaturated 5- or 6-membered heterocyclic group containing 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms in the ring substituted by two substituents '' C 8 alkoxycarbonyl group '', more preferably, the same or different 1 to 3 chlorine atoms or fluorine atoms, one of the above-mentioned ⁇ C 1 -C 3 alkoxy group '', one of the above “To alkylthio group”, one phenyl group or one “ring”
  • the “C 4 -C 7 cycloalkoxycarbonyl group” includes, for example, Such a carbonyl group to which a cycloalkoxy group having 3 to 6 carbon atoms is bonded, preferably a carbonyl group to which a cycloalkoxy group having 4 to 6 carbon atoms is bonded (C 5 to C 5 a 7 cycloalkyl Ano record alkoxy Cal Boniru group), more preferably a carbonyl group bonded cycloalkoxy group is a 5 or 6 carbon atoms (C 6 ⁇ C 7 cycloalkoxy group), preferably more than Is a cyclopentoxycarbonyl group.
  • the “C 3 -C 7 alkenyloxycarbonyl group” is, for example, butyloxycarbonyl, 2-propininoleoxycarbonyl, 1-methyl-12-propynyloxycarbonyl, 2-methyl-2 —Propenyloxycarbonyl, 2-butenyloxycarbonyl, 3-methyl_2-butyroxycarbonyl, 1-methinole — 2-butenyloxycanoleboninole, 3-butenyloxy A carbonyl group to which a straight-chain or branched-chain alkenyloxy group having 2 to 6 carbon atoms such as carbonyl, 2-pentenyloxycarbyl and 5-hexyloxycarboell is bonded.
  • C 3 -C 7 alkynyloxycarbonyl group” ′ is, for example, propargyloxycarbonyl, 1,1-dimethylpropargyloxycarbonyl, 3 A carbonyl having a straight-chain or branched-chain alkynyloxy group having 2 to 6 carbon atoms, such as butyninoleoxycarbonyl, 4-pentienoleoxycarbonyl, and 2-hexynyloxycarbonyl.
  • a carboxyl group (C 3 -C 6 alkynyloxycarbonyl group) having a linear or branched alkynyloxy group having 2 to 5 carbon atoms, more preferably Is a carbonyl group (C 4 -C 6 alkynyloxy group) to which a linear or branched alkynyloxy group having 3 to 5 carbon atoms is bonded, and still more preferably, It is a methylbuteryl group.
  • the “(C t Ce alkylthio) carbonyl group” includes, for example, (methinorethio) canolebonel,
  • it is a carbonyl group to which a linear or branched alkylthio group having 1 to 4 carbon atoms is bonded, and more preferably, a linear or branched alkylthio group having 1 to 3 carbon atoms is bonded.
  • the “(phenylthio) carboyl group substituted by 1 to 5 substituents selected from the group consisting of a halogen atom and an alkyl group” is, for example, a (chlorophenylthio) canolepo -Nore, (dichloro mouth fenylthio) canoleboninole, (trichloro mouth phenylthio) carbonole, (fluorophenylthio) carbonyl, (diphenylolefurofurio) force / repo-norre, (triphenololenophenylenole) (Cho) Canolepo-Nore, (Pentafluoropheninolethio) Canolebonil, (Bromophenol-thio) Canolebo 2 Nore, (Edofueruchirio) Canoleponinore, (Chlorofluorophenylthio) Carbononole, (Mechinor
  • the “(C 1 -C 6 alkoxy) thiocarboyl group” is, for example, (methoxy) thiocarbonyl, (ethoxy) thiocarbonyl, (propoxy) thiocarbonyl, (isopropoxy) thiocarbonyl, (butoxy) thiocarbonyl.
  • a thiocarbonyl group ⁇ (CtCT norecoxy) thiocarbonyl group ⁇ to which a linear or branched alkoxy group having 1 to 4 carbon atoms is bonded, and more preferably a carbon number
  • a 1 to a 3 straight chain or branched chain Chio carbonyl group alkoxy group bonded ⁇ ( ⁇ ⁇ 3 alkoxy) Chio carbonyl group ⁇ still more preferably, (main butoxy) Chio carbonyl group or ( Ethoxy) is a thiocarbonyl group.
  • substituted by halogen atoms and ⁇ 6 1 to 5 substituents Ru is selected from the group consisting of alkyl groups (phenoxy) Chio carbonyl group", where example embodiment, (Kurorofuenokishi) Chiokarubo two Nore, (dichlorophenoxy) thiocarbinole, (trichlorophenoxy) thiocarber, (fluorophenoxy) thiocarbonyl, (difluorophenoxy) thiocarbonyl, (trifluorophenoxy) thiocanolepo-norre, (pentafu) 'Fluorofenoxy) thiocarbonyl, (bromophenoxy) thiocanoleboninole, (eodophenoxy) thiocarbonyl, (chlorofluorophenoxy) thiocarbonyl, (methinolephenoxy) thiocarbol, (ethylfurenoxy)
  • the “C 2 -C 7 alkyldithiocarbonyl group” includes, for example, methyl dithiocanolebonyl, ethyldithiocarbinole, propyldithiocarbonyl, isopropyl pinoresticarbonyl, butyldithiocarbonyl.
  • a thiocarbonyl group (C 2 -C 6 alkyldithiocarber group) to which a linear or branched alkylthio group having 1 to 5 carbon atoms is bonded, more preferably A thiocarbonyl group (C 2 -C 5 alkyldithiocarbonyl group) having a straight-chain or branched-chain alkylthio group having 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms; a number of straight or branched chain alkyl thio group Chio carbonyl group attached (C 2 -C 4 alkyl di Chio carbonyl group), particularly preferably, methyl di Chio group or E chill di Chio carbonyl It is.
  • halogen atom and ⁇ 6 has been phenylalanine di Chio carbonyl group substituted by 1 to 5 substituents Ru is selected from the group consisting of alkyl group", for example, black hole Hue Interview Bruno registration Chio Kano Levonizole, dichloropheninoresitica canolepo-nore, trichlorophenodiresiocarbonyl, fluorophenyldithiocarbonyl, difluorophenyldithiocanolepole, trifluorophenyldithiocarbonyl, pentafluorophenol Nolesithiocarbinole, bromophenyldithiocarbonate, eodophenyldithiocanoleboninole, chlorofluorophenesolecitiocarbonyl, methylpheninoresicarboninole, ethylphenyldithiocarbole, propylf Enildicioka Boenor
  • halogen atom and a phenoxy group substituted with 1 to 5 substituents Ru is selected from the group consisting of ⁇ 6 alkyl group
  • ⁇ 6 alkyl group for example, Kurorofueno alkoxy, dichloro phenoxyethanol, trichloroacetic phenoxyethanol , Phenololenophenoxy, dibenzoolenophenoxy, trifolenorenophenoxy, pentaphenolenophenoxy, bromophenoxy, rhodophenoxy, chlorofluorophenoxy, methinolephenoxy, ethylphenoxy, propinolephenoxy, isopropyl phenoxyethanol, Buchirufuenoki shea, tert- Buchirufuenokishi, pliers Ruff hackberry shea, Kishirufuenokishi like to, the "halogen atom” and the same or different 1 to selected from the group consisting of " ⁇ 6 alkyl group” Phenoic substitute
  • phenyl group (the phenyl group may be substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a C i Ce alkyl group and an alkoxy group).
  • substituents selected from the group consisting of a halogen atom, a C i Ce alkyl group and an alkoxy group.
  • ⁇ - ⁇ Alkoxy group (-anoreoxy) Ci Ce alkoxy group
  • CL Ce alkylthio group (-anoreoxy) Ci Ce alkoxy group
  • cyano group phenoxy group (the phenoxy group is selected from the group consisting of halogen atoms and alkyl groups.
  • a C 1 -C 6 alkyl group substituted by a C 2 -C 7 alkoxycarbonyl group is, for example, a benzyl group, a 2-phenyl-ethylene group or a 1-phenylene group.
  • Echinole methoxymethinole, ethoxymethinole, propoxymethinole, butoxymethyl, pentyloxymethyl, hexyloxymethyl, methoxyxetil
  • One phenolic group one such as ethoxyxetil, methoxypropyl, 4-cyanobutyl, f.enoxymethyl, 2-phenoxetinole, methoxycanoleponinolemethinole, ethoxycanolebonimetin 1 to 5 substituted with 1 to 5 substituents selected from the group consisting of a halogen atom, a 1 to 6 alkyl group and a 1 to C fi alkoxy group.
  • the above-mentioned “ ⁇ to 6 alkyl group” substituted by the above “C 2 -C 7 alkoxycarbonyl group” is preferably one phenyl group, and one above-mentioned “chlorine atom, fluorine atom”.
  • two alkyl groups are bonded together with a nitrogen atom to which they are bonded to form a 5- or 6-membered heterocyclic ring (the heterocyclic ring is one nitrogen atom and one oxygen atom or nitrogen atom ..
  • the heterocyclic ring containing an oxygen atom or a nitrogen atom is a carboxy group bonded at the nitrogen atom, and is preferably N-morpholinecarbyl or N-piperidinecarbonyl.
  • a straight-chain or branched-chain alkyl group is a thiocarbamoyl group bonded to a nitrogen atom, and preferably, a same or different straight-chain or branched-chain alkyl group having 1 to 4 carbon atoms is bonded to the nitrogen atom.
  • a thiocarbamoyl group in which two identical or different linear or branched alkyl groups having 1 to 3 carbon atoms are bonded to a nitrogen atom.
  • a thiocarbamoyl group in which two identical alkyl groups having 1 or 2 carbon atoms are bonded to a nitrogen atom.
  • two alkyl groups are joined together with a nitrogen atom to which they are bonded to form a 5- or 6-membered heterocyclic ring (the heterocyclic ring is one nitrogen atom and one oxygen atom or nitrogen atom,
  • the dialkyl) thiocarbamoyl group which forms) is, for example, N-morpholinethiocarbonyl, N-piperidinethiocarbonyl, N-piperazinethiocarbonyl, N-pyrrolidinethiocarbonyl and N-pyrrolidinethiocarbonyl.
  • heterocycle is a thiocarbol group bonded at the nitrogen atom, and is preferably N-morpholinethiocarbonyl or N-piperidinethiocarbonyl.
  • C ⁇ Cs anolequinole group substituted by 1 to 13 halogen atoms means, for example, monofluoromethyl, monochloromethyl, difluoromethinole, dichloromethinole, trifluoromethyl, Such as Fluoroethyl, Monofluor hexinole, Trifluorenol, Pentafuzoleo ethinole, Heptafluoropropyl, Nonafnorolebutyl, Ndecafluoropentyl and Tridecafluor hexyl, the same or different 1 to 1 3 wherein a Symbol before “halogen atom” is substituted " ⁇ 6 alkyl group", preferably, the same or different 1 to 5 chlorine atoms, fluorine atom or bromine The above-mentioned "-alkyl group” substituted with an atom, more preferably 1 to 3 same or different chlorine atoms or fluorine atoms.
  • R 1 is preferably a hydrogen atom, an alkyl group ⁇ the alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is 3 chlorine atoms, fluorine atoms, yo is replaced by a bromine atom or a Ci C alkyl group les.), 1 or 2 ⁇ ⁇ 4 alkoxy group (said alkoxy group is 1 ⁇ optimum five chlorine Atom, a fluorine atom or a bromine atom.), One C 3 -C 5 alkenyloxy group, one (C t C alkoxy) C 1 -C 4 alkoxy group, one benzyloxy group One C 1 -C 4 alkylthio group, one to three chlorine atoms, fluorine atoms or bromine atoms, one cyano group, one di (C 1 -C 4 alkyl) amino group or one A 5- or 6-membered heterocyclic group (the heterocyclic group
  • phenyl group (the phenyl group is substituted by 1 to 3 substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a C t -C 4 alkyl group.
  • the heterocyclic group contains 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and 1 to alkyl group (the The alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms.) ⁇ , A C 2 -C 8 alkylcarbonyl group (the alkylcarbonyl group is 1 to 3 May be replaced by three chlorine atoms, fluorine atoms or bromine atoms, one CiC alkoxy group or one phenoxy group), benzoyl group (the benzoyl group is a chlorine atom, a fluorine atom, Bromine atom or ⁇ alkyl group Made may be substituted by one to 3 substituents selected from the group.), C 2 -C 5 alkoxycarbonyl group, a di (C 1 -C 4 alkyl) force Rubamoiru group, CLC alkyl Sno Reho alkylsulfonyl group or
  • a hydrogen atom, an alkyl group ⁇ the alkyl group is one C 3 -C 6 cycloalkyl group, one phenol group, one or two CLCS alkoxy groups (the alkoxy group May be substituted by 1 to 3 chlorine atoms or fluorine atoms.),
  • the heterocyclic group is one or two oxygen atoms
  • ⁇ , C 3 -C 6 Shikuroa alkyl group, c 3 -C 4 alkenyl group (said alkenyl group, 1 or 2 'number of chlorine atoms or yo is replaced by a fluorine atom les,.), C 3 -C 4 alkynyl group, phenyl group, 5- or 6-membered Hajime Tamaki (said heterocyclic group is.
  • ⁇ ⁇ 2 alkyl group is one ⁇ ⁇ ⁇ alkoxy group, the one (C 1 -C 2 alkoxy) CL CZ alkoxy group or one ⁇ ⁇ 'C It may be substituted by two alkylthio groups. ⁇ ,
  • C 1 -C 2 alkyl group (the alkyl group, yo substituted by one ⁇ Ji 2 alkoxy group les,.) Is.
  • R 2 and R 3 are preferably the same or different, and are preferably a ⁇ alkyl group ⁇ the alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group
  • the phenyl group may be substituted with one to three substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an alkyl group and a C 4 alkoxy group.), 1 or 2 C 1 -C 4 alkoxy groups, one (CL ⁇ C 4 alkoxy) C i -C 4 alkoxy groups, 1 to 5 chlorine atoms, fluorine atom or bromine atom, or one 5- or 6-membered heterocyclic group (The heterocyclic group contains 1 to 3 oxygen atoms, sulfur atoms, or nitrogen atoms
  • the alkenyl group which 1 to 3 chlorine atoms may be substituted by a fluorine atom or a bromine atom), C 3 -C 5 alkynyl group, phenyl group (the phenyl group may be substituted by 1 to 3 substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an alkyl group and an alkoxy group of 4 ).
  • a 5- or 6-membered heterocyclic group contains 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and is a chlorine atom, a fluorine atom, a bromine atom and a CLC y alkyl group (the alkyl group is And 1 to 3 chlorine atoms, fluorine atoms or bromine atoms.) May be substituted with one or two substituents selected from the group consisting of: Or R 2 and R 3 , together with the carbon atom to which they are attached, are a 4- to 7-membered cycloalkane, cycloalkene or cycloalkanedene ring ⁇ wherein the rings are 1 to 3 number of ⁇ 4 alkyl group, one-alkoxy group, one (C i C Anorekokishi) C 1 -C 4 alkoxy groups, one di (CLCA alkyl) amino group, one Mechirenjiokishi group, By one ethylenedioxy group
  • an alkyl group ⁇ the alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group (the phenyl group is a chlorine atom, a fluorine atom, ⁇ 3 alkyl groups and 1 or 2 to Ru is selected from the group consisting of an alkoxy group may be substituted by a substituent.), one or two C i Cg an alkoxy group, one (C t Cg Alkoxy) CLCS alkoxy group, 1 to 3 chlorine atoms or fluorine atoms or 1 5 or 6 membered heterocyclic group (the heterocyclic group contains 1 or 2 oxygen atoms or nitrogen atoms May be replaced by ⁇ , C 3 ⁇ ⁇ 6 cycloalkyl group, C 3 -C 4 alkenyl group, C 3 -C 4 alkynyl group, phenyl group (said phenyl group is substituted by 1 or 2 ⁇ ⁇ ⁇ alkoxy
  • hexane ring is composed of one or two C 1 -C 2 alkyl groups, one ⁇ - ⁇ 2 alkoxy group, one (C i -C 2 alkoxy) C i Cs alkoxy group, Okishi group may be substituted by one trimethylene di O alkoxy group or one N-(C 1 -C 2 alkoxy) imino group.
  • both represent a methyl group, or R 2 and R 3 together with the carbon atom to which they are attached form a cyclohexane ring (the cyclohexane ring is May be substituted by a C i CzT ⁇ coxyl group, an ethylenedioxy group, a trimethylenedioxy group or an N- ( 2- dialkoxy) imino group.
  • the cyclohexane ring is May be substituted by a C i CzT ⁇ coxyl group, an ethylenedioxy group, a trimethylenedioxy group or an N- ( 2- dialkoxy) imino group.
  • R 4 is preferably a hydrogen atom, a C 2 -C 8 alkylcarboyl group (the alkylcarbonyl group is one to three chlorine atoms, a fluorine atom or a bromine atom, 2 -C 5 alkylcarbonyl O alkoxy group, one C 1 -C 4 alkoxy group or les yo substituted by one phenoxy group,.), C 4 ⁇ C 7 cycloalkyl carboxymethyl El group ⁇ said cycloalkyl
  • the carbonyl group is an alkyl group, a chlorine atom, a fluorine atom and a bromine atom, 1 to 4 substituents selected from the group consisting of 1 or 2 C t to C 4 alkoxy groups, 1 or 2 cyano groups Or one pheny
  • 1 to 3 substituents selected from the group consisting of, from 1-3 CLC alkoxy groups, one C 2 -C 5 alkylcarbonyl Niruokishi group, one C 2 -C 5 alkoxycarbonyl group, one C I ⁇ C 4 alkyl Chiomoto, one C 1 -C 4 alkyl sulfide El group, one C ⁇ -C 4 alkylsulfonyl group, one phenoxy group, of one Shiano group or one It may be substituted by a nitro group.
  • 4-6-membered heterocyclic group said heterocyclic carbo - le groups, 1 to 3 oxygen atoms, a sulfur atom or a nitrogen atom, 1 or 2 ⁇ 4 alkyl group (said alkyl group May be replaced by one to three chlorine atoms, fluorine atoms or bromine atoms.), One or two di-to-dioxy alkoxy groups, one C L to C 4 alkylthio group or one May be substituted by a chlorine atom, a fluorine atom or a bromine atom, or may be condensed with a benzene ring.
  • alkoxycarbonyl group is one to three chlorine atoms, fluorine atoms or bromine atoms, one A C i C alkoxy group, one C 1 -C 4 alkylthio group, one phenyl group (the fuunyl group is selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and an alkyl group Or a 5- or 6-membered heterocyclic group, which may be substituted with 1 to 3 substituents, wherein the heterocyclic group is 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms.
  • (C i C alkoxy) thiocarbonyl group, (phenoxy) thiocarbonyl group (The (phenoxy) thiocarbonyl group is selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and an alkyl group. May be substituted.
  • ⁇ Ji 4 alkyl group ⁇ said ⁇ alkyl group is one, Fueyuru group (said phenyl group is a chlorine atom, a fluorine atom, odor atom, ⁇ 4 alkyl may be substituted by one to 3 substituents selected from the group consisting of groups and CL ⁇ C 4 alkoxy group.), C i C alkoxy groups, (C i CA alkoxy) C 1 -C 4 alkoxy group, CL CA alkylthio group, Shiano group, Fueno alkoxy group (said phenoxy group may be substituted by 1 to 3 substituents selected from a chlorine atom, a fluorine atom, a bromine atom, and C t -C 4 group consisting al kill group Teyo les,.) Or C 2 -C 5 alkoxycarbonyl Les yo is replaced by a carbonyl group.
  • a di (-alkyl) thiocarbamoyl group ⁇ the two alkyl groups in the dialkylthio group are Together with the nitrogen atom to which they are attached, they form a 5- or 6-membered heterocycle (the heterocycle may contain one oxygen atom or nitrogen atom in addition to one nitrogen atom).
  • the heterocycle may contain one oxygen atom or nitrogen atom in addition to one nitrogen atom.
  • a hydrogen atom a C 2 -C 6 alkylcarbonyl group (the alkylcarbonyl group is 1 to 3 chlorine atoms or fluorine atoms, one C 2 -C 4 alkyl group of ⁇ 3 alkoxy or one phenoxy group by replacement by yo been,), C 4 -C 7 cycloalkyl carbo -.
  • Le group said cycloalkyl force Ruponiru group has 1 to 4 ⁇ ⁇ 3 alkyl groups, chlorine atom or fluorine atom,
  • One CLCS alkoxy groups, one Shiano group or one phenyl group may be substituted by one ⁇ ⁇ 3 alkoxy group.) It may be replaced by. ⁇ , C 3 -C 5 alkenyl group (the Aruke -.
  • Le carbonyl group in which one or by two chlorine atoms or fluorine atoms may be substituted
  • Benzoiru group ⁇ those said Benzoiru group, a chlorine atom, fluorine 1 or 2 substituent (s) selected from the group consisting of an atom and a ⁇ - ⁇ ⁇ ⁇ ⁇ 3 alkyl group (the alkynole group may be replaced by 1 to 3 chlorine atoms or fluorine atoms or 1 fuunoxy group).
  • a 4- to 6-membered heterocyclic carbonyl group contains 1 to 3 oxygen, sulfur or nitrogen atoms, and 1 or 2 to 3 alkyl groups (the alkyl groups are , 1 through
  • alkoxycarbonyl group is 1 to 3 chlorine atoms or fluorine atoms, 1 ⁇ alkoxy group, 1 ⁇ 3 alkylthio group, 1 Or a 5- or 6-membered heterocyclic group (the heterocyclic group contains one or two oxygen or nitrogen atoms).
  • a hydrogen atom a C 2 -C 4 alkylcarbonyl group, a cyclopropyl carbonyl group (the cyclopropylcarboyl group may be substituted by one alkyl group), C 3 -C 4 alkenylcarbonyl group, a Benzoiru group or C 2 -C 3 alkoxycarbonyl group,
  • A is preferably a C i -C 4 alkyl group (the alkyl group may be substituted by 1 to 5 chlorine, fluorine or bromine atoms), chlorine atom, fluorine atom, a bromine atom, C 1 -C 4 alkoxy group (said alkoxy group is 1 to It may be replaced by three chlorine, fluorine or bromine atoms.
  • C i C ⁇ alkylthio group, C T ⁇ C 4 alkylsulfonyl group, phenyl group (said phenyl group contains 1 to 3 atoms selected from a chlorine atom, a fluorine atom, the group consisting of bromine and ⁇ 4 alkyl group
  • a 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen, sulfur, or nitrogen atoms, and is a chlorine atom, a fluorine atom, , A bromine atom and a CLCA alkyl group which may be substituted with one or two substituents.),
  • a cyano group, a nitro group, an amino group or a phenoxy group (the phenoxy group is a chlorine atom, a fluorine atom And may be substituted by 1 to 3 substituents selected from the group consisting of a bromine atom and a 4- alkyl group.) And more preferably 3 alkyl groups (the alkyl group may
  • n is preferably 2 or 3.
  • the substitution position of the substituent A is preferably 2,4-, 2,6_, 2,3,6- or 2,4,6_.
  • X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • the “alkali metal salt” includes, for example, a sodium salt, a potassium salt, Lithium salts are preferred, preferably sodium or potassium salts.
  • the “alkaline earth metal salt” includes, for example, a canoledium salt and a magnesium salt, and is preferably a calcium salt.
  • Hydrates of the compound of the present invention are also included in the present invention.
  • the present invention includes a mixture of one kind of optically active substance and several kinds of optically active substances at an arbitrary ratio.
  • R 1 is a hydrogen atom, an alkyl group ⁇ the alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is a chlorine atom, fluorine An atom, a bromine atom, and-may be substituted by 1 to 3 substituents selected from the group consisting of 4 alkyl groups), 1 or 2 ⁇ to 4 alkoxy groups (the alkoxy group is May be substituted by five chlorine, fluorine or bromine atoms.), One C 3 -C 5 anorecheninoleoxy group, one (C 1 -C 4 alkoxy) C L -C 4 alkoxy groups, 1 benzyloxy group, 1 ⁇ to 4 alkylthio group, 1 to 3 chlorine atoms, fluorine or bromine atoms, 1 cyano group, 1 di (C i Ca alkyl) An amino group or one 5- or 6-membered heterocyclic group (the heterocycl
  • C 3 -C 7 cycloalkyl group, C 3 -C 5 alkenyl group (said Arukeyuru groups, 1 to 3 chlorine atoms may be substituted by a fluorine atom or a bromine atom.), C 3 -C 5 An alkynyl group, a phenyl group (the fluor group may be substituted by one to three substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and an alkyl group); 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen, sulfur, or nitrogen atoms, and 1 ⁇ to alkyl group (the alkyl group is 1 to 3 May be substituted by a chlorine atom, a fluorine atom or a bromine atom.) ⁇ , A C 2 -C 8 alkylcarbonyl group (the alkylcarbonyl group may be 1 to 3 chlorine atoms) Atom, fluorine or bromine
  • a benzoyl group (the benzoyl group may be substituted by one to three substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a CLC alkyl group.), C 2 -C 5 alkoxycarbonyl group, di (C i Ca alkyl) dirubamoyl group, An ethyl sulfonyl group (the phenylsulfonyl group may be substituted by 1 to 3 substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a CL to C 4 alkyl group).
  • R 2 and R 3 are the same or different, ⁇ Ji 4 alkyl group ⁇ said alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group (said Fuweniru groups are chlorine atom, fluorine Atom, bromine atom, ⁇ ⁇ ⁇ alkyl group and ⁇ alkoxy group may be substituted by 1 to 3 substituents.), 1 or 2 C t to C 4 alkoxy groups, 1 of ( ⁇ ⁇ 4 alkoxy) ⁇ 4 alkoxy group, 1 to 5 chlorine atoms, fluorine atom or bromine atom, or one 5- or 6-membered Hajime Tamaki (said heterocyclic group is 1 to 3 Containing an oxygen atom, a sulfur atom or a nitrogen atom.
  • C 3 -C 7 cycloalkyl group C 3 -C 5 alkenyl group (the alkenyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms), C 3 -C 5 alkynyl group, Hue - Le group (said Hue - le group, a chlorine atom, a fluorine atom, a bromine atom, 1 to 3 substituents selected from-alkyl groups and ⁇ group consisting 4 alkoxy group Or a 5- or 6-membered heterocyclic group ⁇ the heterocyclic group contains 1 to 3 oxygen, sulfur or nitrogen atoms, and is selected from chlorine, fluorine, bromine and C i
  • a Ca alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms) may be substituted by one or two substituents selected from the group consisting of: Or R 2 and R 3 , together with the carbon atom
  • R 4 is a hydrogen atom, a C 2 -C 8 alkylcarbonyl group (the alkylcarbonyl group is one to three chlorine atoms, a fluorine atom or a bromine atom, one C 2 to C 5 alkyl carbonyl group, 1 number of ⁇ ⁇ 4 alkoxy groups or one phenoxy group by replacement by yo is,.), C 4 -C 7 cycloalkylcarbonyl group ⁇ said cycloalkyl force Ruponiru groups, ⁇ alkyl group, a chlorine atom, 1 to 4 substituents selected from the group consisting of fluorine atoms and bromine atoms, 1 or 2 to alkoxy groups, 1 or 2 cyano groups or 1 phenyl group (the phenyl group is It may be substituted by a C 1 -C 4 alkoxy group.
  • C 3 -C 6 alkenyl group (the alkenyl group is 1 to 3 chlorine atoms may be substituted by a fluorine atom or a bromine atom.), Benzoiru group ⁇ said Benzoiru group, a chlorine atom, A fluorine atom, a bromine atom, and a 4- to 4- alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms, or one phenoxy group).
  • a 4- to 6-membered heterocyclic carbonyl group (the heterocyclic carbonyl group contains 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and 1 or 2 ⁇ to ⁇ 4 alkyl groups (the alkyl groups May be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms.), 1 or 2 C 1 -C 4 alkoxy groups, 1 C i C alkylthio group or 1 chlorine atom , A fluorine atom or a bromine atom, and may be condensed with a benzene ring.
  • a C 2 -C 8 alkoxycarbonyl group ⁇ the alkoxycarbonyl group is 1 to 3 chlorine atoms, fluorine atoms Or a bromine atom, one to an alkoxy group, one C L to C 4 alkylthio group, one phenyl group (the phenol group is a chlorine atom, a fluorine atom, a bromine atoms
  • one 5 or 6-membered Hajime Tamaki (said heterocyclic group is 1 to 3 oxygen atoms, a sulfur atom or a nitrogen atom, a chlorine atom, a fluorine atom, a bromine atom, and ⁇ C 4 alkyl group And may be substituted by one or two substituents selected from the group consisting of:).
  • the (phenoxy) thiocarbonyl group is one to three selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and an alkyl group.
  • a 5- or 6-membered heterocyclic ring (the heterocyclic ring may contain one oxygen atom or one nitrogen atom in addition to one nitrogen atom).
  • alkylsulfonyl Interview group off Yunirusuruhoniru group (said phenylpropyl sulfonyl group, a chlorine atom, a fluorine atom, a bromine atom and CL ⁇ C 4 by 1 to 3 substituents selected from the group consisting of alkyl groups are substitution yo is,.) Or di (C i C alkoxy) thiophosphoryl group;
  • A is ⁇ ⁇ ⁇ alkyl group (the alkyl group, 1 to 5 chlorine atoms may be substituted by a fluorine atom or a bromine atom.), A chlorine atom, a fluorine atom, a bromine atom, ⁇ 4 alkoxy group (the alkoxy group is 1 to 3 chlorine atoms may be substituted by a fluorine atom or a bromine atom.), ⁇ 4 alkylthio group, ⁇ 4 Al Kirusunorehoniru group, phenyl group (said phenyl group is a chlorine atom, May be replaced by 1 to 3 substituents selected from the group consisting of a fluorine atom, a bromine atom and an alkyl group.), A 5- or 6-membered heterocyclic group (the heterocyclic group is oxygen atom, a sulfur atom or a nitrogen atom, a chlorine atom, a fluorine atom, yo substituted by 1 or 2 substituents
  • n force 1, 2, 3, 4 or 5
  • R 1 is a hydrogen atom
  • ⁇ ⁇ Ji 3 alkyl group ⁇ said alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group, one or two C 1 -C 3 alkoxy group (the alkoxy group may be substituted by 1 to 3 chlorine atoms or fluorine atoms.), 1 (C 1 -C 3 alkoxy) ⁇ ⁇ ⁇ 3 alkoxy group, one base Njiruokishi group, one ⁇ ⁇ 3 alkylthio group, 1 to 3 chlorine atoms or fluorine atom, one Shiano groups or one 5 or 6-membered Hajime Tamaki (said heterocyclic
  • the radicals contain one or two oxygen or nitrogen atoms.
  • C 3 -C 6 cycloalkyl group C 3 -C 4 alkenyl group (said alkenyl group is one or two chlorine atoms or les yo are replaced by fluorine atoms,.), C 3 ⁇ C 4 alkynyl group, off group, 5- or 6-membered Hajime Tamaki (said heterocyclic group is also one or two oxygen atoms containing a nitrogen atom.), C 2 -C 6 alkylcarbonyl group, Benzoiru groups, C Two ⁇ C 4 alkoxycarbonyl group, di (Ci Cg alkyl) group rubamoyl group, CL CS alkynolenolephonyl group or phenylsulfonyl group,
  • R 2 and R 3 are the same or different, and an alkyl group ⁇ the alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group (the phenyl group is a chlorine atom, a fluorine atom, May be substituted by one or two substituents selected from the group consisting of an alkyl group and an alkoxy group.), 1 or 2 Ci Cs alkoxy groups, 1 (CL CS anoleoxy) Ci Cs Substituted by an alkoxy group, 1 to 3 chlorine atoms or fluorine atoms, or one 5- or 6-membered heterocyclic group (the heterocyclic group contains one or two oxygen atoms or nitrogen atoms). May be.
  • R 4 is a hydrogen atom, a C 2 -C 6 alkylcarbonyl group (the alkylcarbon group is 1 to 3 chlorine atoms or fluorine atoms, one C 2 -C 4 alkylcarbonyl group, 1 May be substituted with one Ct Cg alkoxy group or one phenoxy group.), A C 4 -C 7 cycloalkylcarbonyl group, wherein the cycloalkylcarbonyl group is one to four Ci-C 3 alkyl groups, chlorine atom or fluorine atom, one C r -C 3 alkoxy group, yo one Shiano group or one phenyl S (the phenyl group may be substituted by one CL ⁇ C 3 alkoxy group les, )).
  • alkenyl group is one or two chlorine atoms or les yo are replaced by fluorine atoms.
  • the alkyl group is selected from the group consisting of a chlorine atom, a fluorine atom and an alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms or fluorine atoms or 1 phenoxy group).
  • substituents one or two-alkoxy group, one C 2 -C 4 alkylcarbonyl O alkoxy group, one C 2 -C 4 an alkoxy carbonyl group, one CLCS alkylthio group, one CLCS Arukirusurufu Ininore group, one C 1 -C 3 alkylsulfonyl of - group, one phenoxy group may be substituted by one sheet ⁇ cyano group or one nitro group.
  • a 4- to 6-membered heterocyclic carbonyl group contains 1 to 3 oxygen, sulfur or nitrogen atoms, and 1 or 2 ⁇ to alkyl groups (the alkyl groups May be substituted by 1 to 3 chlorine atoms or fluorine atoms.), 1 or 2 CLCS alkoxy groups, 1 ⁇ ⁇ . It may be substituted by 3 alkylthio groups or one chlorine atom or fluorine atom, and may be condensed with a benzene ring.
  • C 2 -C 8 alkoxycarboyl group the alkoxycarbonyl group is 1 to 3 chlorine atoms or fluorine atoms, 1 C 1 -C 3 alkoxy group, 1 CLCS alkylthio group, 1 Or a 5- or 6-membered heterocyclic group (the heterocyclic group contains one or two oxygen or nitrogen atoms).
  • A is an alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms or fluorine atoms), a chlorine atom, a fluorine atom, a bromine atom, a Ci CsT alkoxy group, a C 1 -C A 3- alkylthio group, a C 1 -C 3 alkylsulfonyl group, a phenyl group, a 5- or 6-membered heterocyclic group (the heterocyclic group contains one or two oxygen atoms or nitrogen atoms), a cyano group, A nitro group, an amino group or a phenoxy group, n is 1, 2, 3, 4, or 5;
  • X is a compound in which an oxygen atom or a sulfur atom is provided
  • R 1 is-. 2 alkyl group
  • the alkyl group may be substituted by one Ci to C 2 alkoxy group, one (Ci C alkoxy) Ct Cs alkoxy group or one Ci Cz alkylthio group. ⁇ ,
  • R 2 and R 3 are the same or different and each represents a 2- alkyl group; or R 2 and R 3 together with the carbon atom to which they are attached form a cyclohexane ring hexane ring to Sik ports, one or two Ci ⁇ C 2 alkyl group, one C 1 -C 2 alkoxy group, one (C 1 -C 2 alkoxy) CL CZ alkoxy groups, one Echirenjiokishi Group, one trimethylenedioxy group or one N— (C 1 -C 2 alkoxy) imino group.
  • R 4 is a hydrogen atom, a C 2 -C 4 alkylcarbonyl group, a cyclopropylcarbonyl group (the cyclopropylcarbonyl group may be substituted by one to an alkyl group.), A C 3 -C 4 alkenyl A carbonyl group, a benzoyl group or a C 2 -C 3 alkoxy canoleponinole group,
  • A is a methyl group or a chlorine atom
  • n 2 or 3
  • X is an oxygen atom or a sulfur atom
  • R 1 is particularly preferably an alkyl group, which may be substituted by one C 2 alkoxy group.
  • R 2 and R 3 together represent a methyl group, or R 2 and R 3 Together with the carbon atoms that are present, a cyclohexane ring (the cyclohexane ring is a single C i Cz alkoxy group, ethylenedioxy group, trimethylenedioxy group or N— (CiCz alkoxy) imino group May be replaced by ⁇ .
  • R 4 is a hydrogen atom, a C 2 -C 4 alkylcarbonyl group, a cyclopropylcarbon group (the cyclopropylcarbonyl group may be substituted by one methyl group), or a C 2 -C 3 alkoxycarbonyl Group,
  • A is a methyl group
  • ⁇ 2 or 3
  • R 1 is a hydrogen atom, and 0 4 alkyl "the alkyl group, one C 3 -C 7 cycloalkyl group, one phenyl group (said phenyl group is a chlorine atom, a fluorine atom, may be substituted by one to 3 substituents selected from the group consisting of bromine and CL ⁇ C 4 alkyl group.), one or two - alkoxy group (said ⁇ alkoxy group , 1 to 5 chlorine atoms, fluorine atoms or bromine atoms.), 1 C 3 -C 5 alkenyloxy group, 1 (CLCA alkoxy) -C 4 alkoxy group, 1 benzyloxy group, 1 C 1 -C 4 alkylthio group, 1-3 chlorine, fluorine or bromine atoms, 1 cyano group, 1 di (C i -C 4 alkyl) amino Group or one 5- or 6-membered heterocyclic group (the heterocyclic
  • phenyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms.), C 3 -C 5 alkynyl groups, phenyl groups (the phenyl groups are chlorine atoms, fluorine atoms, bromine And a 5- or 6-membered heterocyclic group ⁇ 1 to 3 heterocyclic groups may be substituted with one to three substituents selected from the group consisting of an atom and a CLCA alkyl group.
  • Oxygen atom, sulfur atom or nitrogen Contains one atom, one ⁇ ⁇ .
  • an alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms).
  • ⁇ , C 2 -C 8 alkylcarbonyl group (the alkylcarbonyl group is 1 to 3 chlorine atoms, fluorine atom or bromine atom, it may be substituted by one ⁇ - alkoxy or one Hue phenoxy group .)
  • Benzoiru group (said Benzoiru group, EnsoHara child, fluorine atom, may be substituted by one to 3 substituents selected from the group consisting of bromine and C t -C 4 alkyl group.), C 2 -C 5 alkoxy carbonyl group, a di (C ⁇ 4 alkyl) force Rubamoiru group, C 1 -C 4 alkylsulfonyl group or Hue - Angeles Ruhon
  • R 2 and R 3 are the same or different; 4 alkyl group ⁇ the alkyl group is one C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is a chlorine atom, a fluorine atom, a bromine atom, ⁇ ⁇ .
  • alkyl group and ⁇ ⁇ 4 may be substituted by one to 3 substituents selected from the group consisting of an alkoxy group.), one or two C ⁇ ⁇ C 4 Anorekokishi group, one (CLCA alkoxy) C t C alkoxy group, By 1 to 5 chlorine, fluorine or bromine atoms or one 5 or 6 membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen, sulfur or nitrogen atoms) It may be replaced.
  • C 3 -C 7 cycloalkyl group C 3 -C 5 Arukeeru group (those the Aruke - le groups, 1 to 3 chlorine atoms, yo is replaced by a fluorine atom or a bromine atom les.) , C 3 -C 5 alkynyl group, phenyl group (said phenyl group is a chlorine atom, a fluorine atom, a bromine atom, ⁇ ⁇ .
  • R 2 and R 3 together with the carbon atom to which they are attached, are a 4- to 7-membered cycloacane, cycloalkene or cycloalkanegen ring ⁇ wherein the ring is 1 Or Three ⁇ ⁇ alkyl group, one C 1 -C 4 alkoxy groups, one (C 1 -C 4 alkoxy) C 1 -C 4 alkoxy groups, one di (C 1 -C 4 alkyl) may be substituted with an amino group, one methylenedioxy group, one ethylenedioxy group, one trimethylenedioxy group or one N— (C i C anorekoxy) imino group, any In the position (1), the ring may be interrupted by an oxygen atom, a sulfur atom or a group represented by the formula NR 6a (wherein R 6a represents a C t Ca anoalkyl group). ⁇ ,
  • R 5 is a C 1 -C 4 alkyl group
  • A is a ⁇ to 4 alkyl group (the alkyl group may be substituted by 1 to 5 chlorine atoms, fluorine atoms or bromine atoms), a chlorine atom, a fluorine atom, a bromine atom, a ⁇ ⁇ alkoxy group ( The alkoxy group may be substituted by 1 to 3 chlorine atoms, fluorine atoms, or bromine atoms.),
  • n force 1, 2, 3, 4 or 5
  • R 1 is a hydrogen atom, an alkyl group (the alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group, one or two ⁇ ⁇ 3 alkoxy group (said alkoxy group is yo substituted by 1 to 3 chlorine atoms or fluorine atoms Rere.), one (C 1 -C 3 alkoxy) CLCS alkoxy groups, one base Benzyloxy group, one ⁇ -trialkylthio group, one to three chlorine or fluorine atoms, one cyano group or one 5- or 6-membered heterocyclic group (the heterocyclic group is ⁇ or 2 Containing an oxygen atom or a nitrogen atom.
  • R 2 and R 3 are the same or different, ⁇ Ji 3 alkyl group ⁇ said alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group (said phenyl group is chlorine atom, fluorine atom, - alkyl and ⁇ ⁇ Ru is selected from the group consisting of 3 alkoxy group 1 or the two substituents may be substituted.), one or two - an alkoxy group, one (C 1 -C 3 alkoxy) C 1 -C 3 alkoxy group, 1 to 3 chlorine atoms or fluorine atoms, or 1 5- or 6-membered heterocyclic group (the heterocyclic group is one or two oxygen atoms Or containing a nitrogen atom.).
  • R 5 is a C 1 -C 3 alkyl group
  • A is a ⁇ -alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms or fluorine atoms), a chlorine atom, a fluorine atom, a bromine atom, a ⁇ 3 alkoxy group, a CL CS Alkylthio group, C 1 -C 3 alkylsulfonyl group, pheninole group, 5- or 6-membered heterocyclic group (the heterocyclic group is .1 or 2 oxygen atoms or nitrogen atoms Contains offspring. ), A cyano group, a nitro group, an amino group or a phenoxy group; n force 1, 2, 3, 4 or 5;
  • X is an oxygen atom or a sulfur atom
  • R 1 is an alkyl group ⁇ where the alkyl group is one C 1 -C 2 alkoxy group, one (CL CZ alkoxy) C t -C 2 alkoxy group or It may be substituted by one to two alkylthio groups. ⁇ ,
  • R 2 and R 3 are the same or different and each represents a ⁇ to ⁇ 2 alkyl group, or R 2 and R 3 are taken together with the carbon atom to which they are attached to form a cyclohexane ring hexane ring to Sik ports, one or two ⁇ ⁇ 2 alkyl groups, one ⁇ ⁇ 2 alkoxy groups, one (Ci Cs alkoxy) Ci Cs alkoxy group, one Echirenjiokishi group one May be substituted by a trimethylenedioxy group or one N- (CiCsalkoxy) imino group.
  • ⁇
  • R 5 is a C 1 -C 2 alkyl group
  • A is a methyl group or a chlorine atom
  • X is an oxygen atom or a sulfur atom
  • R 1 is an alkyl group (the alkyl group may be substituted by one C t Cz alkoxy group.)
  • R 2 and R 3 together represent a methyl group, or R 2 and R 3 together with the carbon atom to which they are attached form a cyclohexane ring (the cyclohexane ring is 1 number of CL ⁇ C 2 alkoxy group, Echirenjiokishi group, trimethylene di O alkoxy group, or N- (C L ⁇ C 2 alkoxy) Les yo is replaced by an imino group.
  • ⁇
  • R 5 is a methyl group
  • A is a methyl group
  • R 1 is a hydrogen atom, ⁇ ⁇ 4 alkyl" the alkyl group, 1 C 3 -C 7 cycloalkyl groups, one phenyl group (the phenyl group is a group consisting of 1 to 3 substituents selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom and a CLCA alkyl group)
  • One or two CLC alkoxy groups (the alkoxy group may be substituted by 1 to 5 chlorine atoms, fluorine atoms or bromine atoms), and one C 3 -C 5 alkenyl - Ruokishi group, one ( ⁇ ⁇ 4 alkoxy) C t -C 4 ⁇ Kokishi group, one Benjiruokishi group, one C 1 -C 4 alkylthio group, 1 to 3 chlorine Atom, fluorine or bromine atom, one cyano group, one diamine
  • heterocyclic group contains 1 to 3 oxygen, sulfur, or nitrogen atoms, and is a chlorine atom, a fluorine atom, A bromine atom and an alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms). Les ,. ⁇ .
  • C 3 -C 7 consequent opening alkyl group
  • C 3 -C 5 alkenyl group (said alkenyl group is 1 to 3 chlorine atom may be substituted by a fluorine atom or a bromine atom.), C 3 ⁇ C 5 alkynyl group, phenyl group (said Fueeru group, a chlorine atom, a fluorine atom, may be substituted by one to 3 substituents selected from a bromine atom, and C 1 -C 4 7 alkyl group consisting of group.) , 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms, and 1 to an alkyl group (the alkyl group is 1 to 3 chlorine atoms Atom, a fluorine atom or a bromine atom, and may be substituted with a)), a C 2 -C 8 alkylcarbol group (the alkylcarbonyl group is a group of
  • R 2 and R 3 are the same or different, ⁇ 4 alkyl group ⁇ said alkyl group is 1 C 3 -C 7 cycloalkyl group, one phenyl group (the phenyl group is a 1 to 3 substituent selected from the group consisting of a chlorine atom, a fluorine atom, a bromine atom, an alkyl group and a ⁇ alkoxy group) ), 1 or 2 C i -C 4 alkoxy groups, 1 (C 1 -C 4 alkoxy) C 1 -C 4 alkoxy group, 1 to 5 chlorine atoms, fluorine Atom or bromine atom or one 5- or 6-membered heterocyclic group (the heterocyclic group contains 1 to 3 oxygen, sulfur or nitrogen atoms).
  • C 3 -C 7 cycloalkyl group C 3 -C 5 alkenyl group (those the Aruke - le groups, 1 to 3 chlorine atoms, yo is replaced by a fluorine atom or a bromine atom les.)
  • a C 3 -C 5 alkynyl group a phenyl group (wherein the phenyl group is a chlorine atom, a fluorine atom, a bromine atom, a ⁇ ⁇ ⁇ alkyl group and a ⁇ ⁇ .
  • the heterocyclic group contains 1 to 3 oxygen, sulfur, or nitrogen atoms, and is a chlorine, fluorine, or bromine atom.
  • Atom and a CLCA alkyl group the alkyl group may be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms).
  • the alkyl group may be substituted by one or two substituents selected from the group consisting of: ⁇ Or R 2 and R 3 are the Together with the carbon atom to which it is attached, forms a 4- to 7-membered cycloalkane, cycloalkene or cycloalkanegen ring (wherein the ring comprises 1 to 3 C 1 -C 4 alkyl groups, 1 C 1 to C 4 alkoxy group, 1 ( ⁇ to 4 alkoxy) alkoxy group, 1 di (C 1 to C 4 alkyl) amino group, 1 methylenedioxy group, 1 ethylenedioxy group, 1 may also number of trimethylene di O alkoxy group substituted by one N-(CLCA alkoxy) imino group, the ring is an oxygen atom at an arbitrary position, a sulfur atom or a group represented by the formula NR 6a (wherein , R 6a represents an alkyl group, and is interrupted by).
  • R 5 is a C i C alkyl group
  • alkyl groups (the alkyl groups may be substituted by 1 to 5 chlorine atoms, fluorine atoms or bromine atoms), chlorine atoms, fluorine atoms, bromine atoms, C i C alkoxy groups (the alkoxy groups are May be substituted by 1 to 3 chlorine atoms, fluorine atoms or bromine atoms.), ⁇ ⁇ ⁇ Alkylthio group, ⁇ 4 alkylsulfonyl group, phenyl group (the phenyl group is chlorine atom, fluorine atom, bromine Atoms and ⁇ ⁇ . It may be replaced by 1 to 3 substituents selected from the group consisting of 4 alkyl groups.
  • heterocyclic group contains 1 to 3 oxygen, sulfur, or nitrogen atoms, and is selected from chlorine, fluorine, bromine, and C i -C 4 alkyl
  • a cyano group, a nitro group, an amino group or a phenoxy group (the phenoxy group is a chlorine atom, a fluorine atom, a bromine atom and And may be substituted by 1 to 3 substituents selected from the group consisting of 4 alkyl groups.
  • n 1, 2, 3, 4 or 5
  • R 1 is a hydrogen atom, ⁇ .3 alkyl group ⁇ said alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group, one or two A C i Cs alkoxy group (the alkoxy group may be substituted by 1 to 3 chlorine atoms or fluorine atoms), 1 (C 1 -C 3 alkoxy) C 1 -C 3 alkoxy group, 1 number of base Njiruokishi group, one ⁇ ⁇ 3 alkylthio group, 1 to 3 chlorine atoms or fluorine atom, one Shiano groups or one 5 or 6-membered Hajime Tamaki (said heterocyclic group is .
  • yo containing one or two oxygen atoms or nitrogen atoms
  • yo is replaced by Les, ⁇ , C 3 -C 6 cycloalkyl group, C 3 -C 4 alkenyl group (said Aruke -. le group, 1 or by two chlorine atoms or fluorine atoms may be substituted), C 3 -C 4 alkynyl group, Hue -.
  • 5 young Ku is 6-membered Hajime Tamaki (said heterocyclic group is also one or two oxygen atoms containing a nitrogen atom.), C 2 -C 6 alkylcarbonyl group, Benzoiru group, C 2 -C 4 alkoxycarbonyl A di (C 1 -C 3 alkyl) group, a carbamoyl group, a CLCS anolequinoresnolefonyl group or a phenylsulfoyl group;
  • R 2 and R 3 are the same or different and each represents an alkyl group ⁇ the alkyl group is one C 3 -C 6 cycloalkyl group, one phenyl group (the phenyl group is a chlorine atom, fluorine Atom, a C i -C 3 alkyl group and a C t -C 3 alkoxy group, and may be substituted with one or two substituents selected from the group consisting of), one or two alkoxy groups.
  • R 5 is a C 1 -C 3 alkyl group.
  • A is-alkyl group (the alkyl group may be substituted by 1 to 3 chlorine atoms or fluorine atom.), A chlorine atom, a fluorine atom, a bromine atom, C 1 -C 3 7 alkoxy groups, C 1 -C 3 alkylthio group, Ji ⁇ Ji; ⁇ alkylsulfonyl group, phenyl group, 5- or 6-membered Hajime Tamaki (said heterocyclic group containing one or two oxygen atoms or ChissoHara child.) , A cyano group, a nitro group, an amino group or a phenoxy group, and n is 1, 2, 3, 4, or 5,
  • X is an oxygen atom or a sulfur atom
  • R 1 is, ⁇ ⁇ ⁇ alkyl group ⁇ said alkyl group is one C 1 -C 2 alkoxy group, one ( ⁇ ⁇ . 2 alkoxy) - ⁇ alkoxy Or may be substituted by one Ci Cz alkylthio group.
  • R 2 and R 3 are the same or different, ⁇ represents 2 alkyl group, or, R 2 and R 3, connexion such together with the carbon atoms to which they are attached, hexane ring (the consequent cyclohexane
  • the mouth hexane ring has one or two C 1 -C 2 alkyl groups, one ⁇ - ⁇ 2 alkoxy group, one ((-?? alkoxy) C 1 -C 2 alkoxy group, one May be substituted by one ethylenedioxy group, one trimethylenedioxy group or one N— (C 1 -C 2 alkoxy) imino group.
  • R 5 is a C 1 -C 2 alkyl group
  • A is a methyl group or a chlorine atom
  • n 2 or 3
  • a compound that is an oxygen atom or a sulfur atom A compound that is an oxygen atom or a sulfur atom
  • R 1 is, ⁇ ⁇ 2 alkyl group (the alkyl group may be substituted by one C 1 -C 2 alkoxy group.),
  • R 2 and R 3 together represent a methyl group, or R 2 and R 3 together with the carbon atom to which they are attached form a cyclohexane ring (the cyclohexane ring is 1 It may be substituted by one CiCz alkoxy group, ethylenedioxy group, trimethylenedioxy group or N- (CLCSalkoxy) imino group.
  • CiCz alkoxy group ethylenedioxy group
  • trimethylenedioxy group trimethylenedioxy group or N- (CLCSalkoxy) imino group.
  • R 5 is a methyl group
  • A is a methyl group
  • n 2 or 3
  • a compound in which X is an oxygen atom or a sulfur atom is shown in Tables 1 to 12 below, but the present invention is not limited to these compounds.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • iPr represents an isopropyl group
  • cPr represents a cyclopropyl group
  • cPr (l-Me, 2, 2_C1 2 ) is 1-methyl-1,2,2-dichlorocyclopropyl group
  • Bu is butyl group
  • tBuJ is tert-butyl group
  • iBu is is isobutyl group
  • sBu is the sec- butyl group
  • cBu is Shikurobuchinore group
  • cP en t cyclopentyl group
  • cHex means alkoxy Le group cycloheteroalkyl, "2, 6 - Cl 2, 4- CF 3 " is 2 , 6-dichloro-1-4-triphenololemethyl group
  • Ac is an acetyl group
  • CH 2 CH CHC1 Me Me H-192
  • CH 2 CH CHC1 Me Me Me COtBu-193
  • CH 2 CH CHC1 Me Me Me C0CH 2 tBu-194
  • CH 2 CH CHC1 Me Me Me C (S) SEt-195 CH 2 stroke e 2 Me Me H

Abstract

Cette invention a trait à des dérivés de dihydropyrrole à substitution N, correspondants à la formule générale (I), ou à leurs sels. Dans cette formule, R1 représente un hydrogène, un alkyle ou analogue, R2 et R3 représentent, chacun de manière indépendante, un alkyle ou analogue, ou bien R2 et R3, avec l'atome de carbone auxquels ils sont liés, représentent ensemble un noyau de cinq à sept chaînons ou analogue, A représente un alkyle ou analogue, n est un nombre entier dont la valeur est comprise entre 1 et 5 et X représente un oxygène, un soufre, un sulfinyle ou un sulfonyle.
PCT/JP2000/002848 1999-05-11 2000-04-28 Dérivés de dihydropyrrole à substitution n WO2000068196A1 (fr)

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WO2004024688A1 (fr) * 2002-08-28 2004-03-25 Bayer Cropscience Aktiengesellschaft Kétoénoles spirocycliques substitués
WO2005044791A2 (fr) * 2003-11-05 2005-05-19 Bayer Cropscience Aktiengesellschaft Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle
JP2009538844A (ja) * 2006-06-02 2009-11-12 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 アルコキシアルキル置換環状ケトエノール
WO2010063670A1 (fr) * 2008-12-02 2010-06-10 Syngenta Participations Ag N-oxyamides spirohétérocycliques utilisés comme pesticides
CN102245028A (zh) * 2008-12-12 2011-11-16 先正达参股股份有限公司 用作农药的螺杂环n-氧基哌啶
WO2011151249A3 (fr) * 2010-05-31 2012-02-02 Syngenta Participations Ag Procédé permettant de lutter contre les hémiptères résistants aux néonicotinoïdes
CN103003276A (zh) * 2010-05-31 2013-03-27 先正达参股股份有限公司 作为杀虫剂有用的1,8-二氮杂螺[4.5]癸烷-2,4-二酮衍生物
JP2013527208A (ja) * 2010-05-31 2013-06-27 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 作物を増強する方法
US20130210625A1 (en) * 2010-05-31 2013-08-15 Syngenta Crop Protection Llc Spiroheterocyclic pyrrolidine derivatives based pesticides
US8518985B2 (en) 2009-03-11 2013-08-27 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
CN103402979A (zh) * 2011-01-05 2013-11-20 先正达参股股份有限公司 化学化合物
US9096560B2 (en) 2008-07-03 2015-08-04 Syngenta Limited 5-heterocyclylalkyl-3-hydroxy-2-phenylcyclopent-2-enones as herbicides
CN106431897A (zh) * 2016-09-27 2017-02-22 宿迁科思化学有限公司 一种2,4,6‑三甲基苯乙酰氯的新合成工艺

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US7754654B2 (en) 2002-08-28 2010-07-13 Bayer Cropscience Ag Substituted spirocyclic ketoenols
WO2004024688A1 (fr) * 2002-08-28 2004-03-25 Bayer Cropscience Aktiengesellschaft Kétoénoles spirocycliques substitués
JP2006503027A (ja) * 2002-08-28 2006-01-26 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 置換スピロ環状ケトエノール類
JP4722483B2 (ja) * 2002-08-28 2011-07-13 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 置換スピロ環状ケトエノール類
US8314254B2 (en) 2002-08-28 2012-11-20 Bayer Cropscience Ag Substituted spirocyclic ketoenols
WO2005044791A3 (fr) * 2003-11-05 2005-08-11 Bayer Cropscience Ag Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle
WO2005044791A2 (fr) * 2003-11-05 2005-05-19 Bayer Cropscience Aktiengesellschaft Derives d'acide tetramique spirocycliques substitues par 2-halogeno-6-alkylphenyle
JP2009538844A (ja) * 2006-06-02 2009-11-12 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 アルコキシアルキル置換環状ケトエノール
US9096560B2 (en) 2008-07-03 2015-08-04 Syngenta Limited 5-heterocyclylalkyl-3-hydroxy-2-phenylcyclopent-2-enones as herbicides
CN102238871A (zh) * 2008-12-02 2011-11-09 先正达参股股份有限公司 用作农药的螺杂环n-氧基酰胺
WO2010063670A1 (fr) * 2008-12-02 2010-06-10 Syngenta Participations Ag N-oxyamides spirohétérocycliques utilisés comme pesticides
CN102245028A (zh) * 2008-12-12 2011-11-16 先正达参股股份有限公司 用作农药的螺杂环n-氧基哌啶
CN102245028B (zh) * 2008-12-12 2014-12-31 先正达参股股份有限公司 用作农药的螺杂环n-氧基哌啶
US8518985B2 (en) 2009-03-11 2013-08-27 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
US9045390B2 (en) 2009-03-11 2015-06-02 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
WO2011151249A3 (fr) * 2010-05-31 2012-02-02 Syngenta Participations Ag Procédé permettant de lutter contre les hémiptères résistants aux néonicotinoïdes
US20130210625A1 (en) * 2010-05-31 2013-08-15 Syngenta Crop Protection Llc Spiroheterocyclic pyrrolidine derivatives based pesticides
JP2013527208A (ja) * 2010-05-31 2013-06-27 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト 作物を増強する方法
CN103002739A (zh) * 2010-05-31 2013-03-27 先正达参股股份有限公司 控制抗新烟碱的半翅目的方法
CN103003276A (zh) * 2010-05-31 2013-03-27 先正达参股股份有限公司 作为杀虫剂有用的1,8-二氮杂螺[4.5]癸烷-2,4-二酮衍生物
CN103002739B (zh) * 2010-05-31 2015-09-09 先正达参股股份有限公司 控制抗新烟碱的半翅目的方法
CN103402979A (zh) * 2011-01-05 2013-11-20 先正达参股股份有限公司 化学化合物
CN106431897A (zh) * 2016-09-27 2017-02-22 宿迁科思化学有限公司 一种2,4,6‑三甲基苯乙酰氯的新合成工艺

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