WO2005073165A1 - アミド誘導体及びその製造方法ならびにその殺虫剤としての使用方法 - Google Patents

アミド誘導体及びその製造方法ならびにその殺虫剤としての使用方法 Download PDF

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Publication number
WO2005073165A1
WO2005073165A1 PCT/JP2004/019770 JP2004019770W WO2005073165A1 WO 2005073165 A1 WO2005073165 A1 WO 2005073165A1 JP 2004019770 W JP2004019770 W JP 2004019770W WO 2005073165 A1 WO2005073165 A1 WO 2005073165A1
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WO
WIPO (PCT)
Prior art keywords
group
alkyl
phenyl
atom
general formula
Prior art date
Application number
PCT/JP2004/019770
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
Kei Yoshida
Takeo Wakita
Hiroyuki Katsuta
Akiyoshi Kai
Yutaka Chiba
Kiyoshi Takahashi
Hiroko Kato
Nobuyuki Kawahara
Michikazu Nomura
Hidenori Daido
Junji Maki
Shinichi Banba
Original Assignee
Mitsui Chemicals, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to US10/587,990 priority Critical patent/US8168825B2/en
Priority to EP04808120.2A priority patent/EP1714958B9/en
Priority to CN2004800425133A priority patent/CN1926094B/zh
Priority to BR122015027139A priority patent/BR122015027139B1/pt
Priority to BR122015015718A priority patent/BR122015015718B1/pt
Priority to DK04808120.2T priority patent/DK1714958T3/en
Priority to NZ548793A priority patent/NZ548793A/en
Priority to CA2554437A priority patent/CA2554437C/en
Priority to AU2004315003A priority patent/AU2004315003B2/en
Application filed by Mitsui Chemicals, Inc. filed Critical Mitsui Chemicals, Inc.
Priority to JP2005517392A priority patent/JP4673748B2/ja
Priority to ES04808120.2T priority patent/ES2619203T3/es
Priority to BRPI0418471A priority patent/BRPI0418471B1/pt
Publication of WO2005073165A1 publication Critical patent/WO2005073165A1/ja
Priority to IL176872A priority patent/IL176872A/en
Priority to EG2006070704A priority patent/EG26976A/xx
Priority to IL211894A priority patent/IL211894A0/en
Priority to US13/427,176 priority patent/US8563736B2/en
Priority to US14/033,005 priority patent/US8710234B2/en
Priority to US14/220,673 priority patent/US9185912B2/en
Priority to US14/854,627 priority patent/US9920026B2/en
Priority to US15/871,552 priority patent/US10435385B2/en
Priority to US16/552,032 priority patent/US10995081B2/en
Priority to US17/208,474 priority patent/US11760742B2/en
Priority to US18/229,277 priority patent/US20230373947A1/en

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    • C—CHEMISTRY; METALLURGY
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    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
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    • C07C237/48—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system of the same carbon skeleton
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
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    • C07D207/40—2,5-Pyrrolidine-diones
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Definitions

  • a 2 , A 3 , A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • Ri and R 2 each represent a hydrogen atom, an alkyl group which may be substituted, or a CI—C 4 alkyl group which may be substituted;
  • Gi and G 2 each represent an oxygen atom or a sulfur atom
  • X may be the same or different, and represents a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, or a trifluoromethyl group, n represents an integer of 0 to 4, and
  • Q Q 2 represents This represents a phenyl group which may be substituted, a naphthyl group which may be substituted, and a heterocyclic group which may be substituted.
  • the present invention relates to a compound represented by the following formula, an insecticide containing the compound as an active ingredient, a method for producing the same, and a method for using the same.
  • WO 2000/55120 Panfrets et al. And US Pat. No. 6,548,514 disclose compounds similar to the compounds of the present invention for pharmaceutical use, but there is no description of activity against insects. Also, it is clear that the compounds are within the scope of the claims of the present invention.
  • Patent Document 2 US Patent No. 6548514
  • Patent Document 3 International Publication No. 2000/7980 Pamphlet
  • Patent Document 4 US Patent Publication No. 2002-032238 Disclosure of the Invention
  • An object of the present invention is to provide an insecticide having a high insecticidal effect.
  • another object of the present invention is a compound represented by the general formula (1), a method for producing the compound, an insecticide containing the compound as an active ingredient, and the compound and another insecticide and / or sterilization
  • An object of the present invention is to provide a method for controlling pests which uses a combination of agents.
  • the compound of the present invention is a novel compound not described in the literature and has a remarkably excellent insecticidal effect.
  • compounds not described in the literature are useful intermediates for producing the compounds of the present invention. As a result, the present invention has been completed.
  • the present invention is as follows.
  • AA 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • Ri and R 2 each represent a hydrogen atom, an alkyl group which may be substituted, or a CI—C 4 alkyl carpinyl group which may be substituted
  • G 2 each represents an oxygen atom Or a sulfur atom
  • X may be the same or different, and represents a hydrogen atom, a halogen atom, a C1 -C3 alkyl group, a trifluoromethyl group
  • n represents an integer of 0 to 4, and is substituted
  • n represents a phenyl group which may be substituted, a naphthyl group which may be substituted, or a heterocyclic group which may be substituted
  • Q 2 is a phenyl group or a heterocyclic group having one or more substituents, and the substitution thereof At least one of the groups is C1 C4 haloalkoxy group, C2-C6 perfluoroalkyl group, C1 C6 perfluoroalkylthio group, C1 C6 C perfluor
  • Ri and R 2 each represent a hydrogen atom or a C 1 -C 4 alkyl group
  • X may be the same or different, and is a hydrogen atom, a halogen atom, or a trifluoromethyl group,
  • a heterocyclic group is a pyridyl group, a pyridyl group, a pyridine-N-hydroxy group, a pyrimidinyl group, a pyridazyl group, a pyrazyl group, a furyl group, a chenyl group, an oxazolyl group, an isoxazolyl group, an oxazolazolyl group, a thiazolyl group , Isothiazolyl group, imidazolyl group, triazolyl group, pyrrolyl group, pyrazolyl group, or tetrazo Indicates a rill group. ),
  • halogen atom CI-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2'-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, CI-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkyl sulfonyl group, C1-C4 alkylamino group, di C1-C4 alkylamino group, cyan
  • ⁇ and Y 5 may be the same or different, and a halogen atom, a CI-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 octaloalkylthio group, a C1-C3 An alkylsulfinyl group, a C1-C3 haloalkylsulfinyl group, a C1 C3 alkylsulfonyl group, a C1 C3 haloalkylsulfonyl group, and a cyano group are shown, and the 3 is a C2-C6 halofluoroalkyl group, a C1-C6 perfluoroalkyl group.
  • ⁇ 6 and ⁇ 9 may be the same or different, halogen atoms, C 1 -C 4 al Cyl group, C1-C4 haloalkyl group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 valo An alkylsulfonyl group or a cyano group is shown, and Y 8 is a C 1 -C 4 haloalkoxy group, a C 2 -C 6 perfluoroalkyl group, a C 1 -C 6 perfluoroalkylthio group, a C 1 -C 6 perfluoroalkyl sulfur group And a C 1 -C 6 perfluoroalkylsulfonyl group,
  • Y 5 may be the same or different, and is a halogen atom, a CI-C4 alkyl group, a CI-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 octaalkylthio group, a C1-C3 alkylsulfinyl Group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 open alkylsulfonyl group, cyano group, and ⁇ 3 is a C1-C6 perfluoroalkylthio group, C1-C6 Pas one Furuo port alkylsulfinyl group, a C1-C6 Pas one full O b alkyl sulfonyl group, or Upsilon 2, Upsilon 4 is a hydrogen atom, a halogen atom, represented
  • Y 6 and ⁇ 9 may be the same or different, and halogen atoms, C1 to C4 alkyl groups, C1 to C4 haloalkyl groups, C1 to C3 alkylthio groups, C1 to C3 haloalkyl thio groups, C1 to C3 Alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkylsulfonyl group, cyano group, and ⁇ 8 represents C1-C4 haloalkoxy group, C1-C6 perfluoro
  • R 7 represents a hydrogen atom, a halogen atom, or a C 1 -C 4 alkyl group), and R 7 represents a hydrogen atom, a C 1 -C 6 perfluoroalkylsulfinyl group, or a C 1 -C 6 perflu
  • halogen atom C1-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 Haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 octaloalkylthio group, C1-C3 alkyl Sulfinyl group, CI-C3 group, sulfonylsulfinyl group, C1-C3 alkyl sulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, C1-C4 alkyl amino group, di C1-C4 alkyl group,
  • Y 5 may be the same or different, a halogen atom, CI- C4 al Kill group, CI- C4 haloalkyl group, CI- C3 alkylthio group, C1- C3 Haroaruki thio group, C1-C3 alkyl sulfinyl group, a C1-C3 haloalkylsulfinyl groups, C1 one C3 alkylsulfonyl groups, C1 one C3 haloalkylsulfonyl group, shea ⁇ cyano group, Upsilon 3 represents a C2-C6 Pafuruo port alkyl group, Upsilon 2, Upsilon 4 represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group) or a general formula (3)
  • Y 6 and ⁇ 9 may be the same or different, and halogen atoms, C1 to C4 alkyl groups, C1 to C4 haloalkyl groups, C1 to C3 alkylthio groups, C1 to C3 haloalkyl thio groups, C1 to C3 alkylsulfinyl group, a C1-C3 haloalkylsulfinyl groups, C1 one C3 alkylsulfonyl group, C1- C3 haloalkylsulfonyl go, shea ⁇ cyano group, Upsilon 8 represents a C2- C6 per full O b alkyl group, Upsilon 7 represents a hydrogen atom, a halogen atom, or a C1-C4 alkyl group.
  • ⁇ and X 2 each represent a hydrogen atom or a fluorine atom
  • X 3 and X 4 are hydrogen atoms, '
  • RR 2 has other if either one is a hydrogen atom C1 one C4 alkyl group der Luke are both C1 one C4 alkyl group,
  • Gi, G 2 is an oxygen atom or a sulfur atom,-
  • Qi is a phenyl group
  • halogen atom C1 C4 alkyl group, C1 C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halo cycloalkyl group,
  • C1-C3 haloalkylthio group C1-C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 haloalkyl sulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group , Cyano group, nitro group, hydroxy group, C 1 -C 4 alkyl carbonyl group, C 1 C 4 alkyl carbonyloxy group, C 1 -C 4 alkoxy carbonyl group, acetyl amino group, one or more same or different selected from phenyl group A substituted phenyl group having one or more substituents,
  • heterocyclic group means pyridyl group, pyridine-N-hydroxy group, pyrimidinyl group, pyridazyl group, pyrazyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group , Isothiazolyl group, And an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group or a tetrazolyl group.
  • halogen atom CI-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 octaoalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkyl group,
  • halogen atom C1 -C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C3 alkoxy group, CI-C3 haloalkoxy group, CI-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 octaalkylsulfinyl group, C1-C3 alkylsulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, C1-C4 alkylamino group, di-Ci-C4 alkyl group,
  • halogen atom CI-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 Haloalkynyl group, C3 to C6 cycloalkyl group, C3 to C6 halocycloalkyl group, C1 to C3 alkoxy group, CI to C3 haloalkoxy group, C1 to C3 alkylthio group, C1 to C3 haloalkylthio group, C1 to C3 alkyl Sulfinyl group, CI-C3 8-alkylsulfonyl group, C1-C3 alkylsulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, C1-C4 alkylamino group, di-C1-C4 alkylamino group, cyan
  • [7] in the general formula (1) is a nitrogen atom or an oxidized nitrogen atom, and A 2 , A 3 and A 4 are carbon atoms, and R 2 is a hydrogen atom or a CI-C 4 alkyl, respectively.
  • halogen atom CI-C4 alkyl group, C1-C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3-C6 haloalkyl group C1-C3 alkoxy group C1-C3 haloalkoxy group C1-C3 alkylthio group C1-C3 haloalkylthio group C1-C3 alkylsulfinyl group C1-C3 octaalkylsulfinyl group C1-C3 alkylsulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, C1 C4 alkylamino group, di C1-C4 alkylamino group, cyano group, nitro group,
  • a 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • Ri represents a hydrogen atom, a C1-C4 alkyl group, a C1-C4 alkyl group, Gi and G 2 each represent an oxygen atom or a sulfur atom, and X may be the same or different, and is a hydrogen atom , A halogen atom, a C1-C3 alkyl group which may be substituted, a trifluoromethyl group, n represents an integer of 0 to 4,
  • halogen atom C1 C4 alkyl group, C1 C4 haloalkyl group, C2-C4 alkenyl group C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 haloalkynyl group, C3-C6 cycloalkyl group, C3 -C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1 C3 haloalkylthio group, CI- C3 alkylsulfinyl group, C1-C3 haloalkylsulfinyl group, C1- C3 alkylsulfonyl group, C1-C3 eight-membered alkyl Sulfonyl group, C 1 -C 4 alkylamino group, di C 1 -C 4 alkylamino group,
  • the heterocyclic group is a pyridyl group, a pyridine-N-oxide group, a pyrimidinyl group, a pyridazyl group, a biladyl group, a furyl group, a chenyl group, an oxazolyl group, an isoxazolyl group, an oxazolazolyl group, a thiazolyl group , Isothiazolyl group, imidazolyl group, triazolyl group, pyrrole group, pyrazolyl group or tetrazolyl group), or-a halogen atom, C1 C4 alkyl group, C1 C4 haloalkyl group, C2-C4 alkenyl group, C2 -C4 haloalkenyl group, C2-C4 arginyl group, C2-C4 eight-membered alkynyl group, C3-C6
  • a substituted heterocyclic group having one or more identical or different substituents selected from a group, C 1 C 4 alkylcarbonyloxy group, C 1 -C 4 alkoxycarbonyl group, acetylamino group, and phenyl group (hetero The ring group is as defined above), and Hal is chlorine or bromine.
  • R 2 is a hydrogen atom, an alkyl group which may be substituted, a CI-C 4 alkyl group which may be substituted, and a Q 2 is a phenyl group which may be substituted, Represents an optionally substituted naphthyl group or an optionally substituted heterocyclic group.
  • a 2 , A 3 and A 4 each represent a carbon atom, a nitrogen atom or an oxidized nitrogen atom
  • 3 ⁇ 4 L and R 2 each represent a hydrogen atom, a C1 C4 alkyl group, a C1 C4 alkyl carpol Group, and '
  • G 2 represents an oxygen atom or a sulfur atom
  • X may be the same or different, and represents a hydrogen atom, a halogen atom, a C1 -C3 alkyl group which may be substituted, a trifluoromethyl group, n represents an integer of 0 to 4, and
  • Y 5 may be the same or different, and is a halogen atom, a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C3 alkylthio group, a C1-C3 haloalkylthio group, a C1-C3 alkylsulfinyl group C1-C3 8-membered alkyl sulfinyl group, C1-C3 alkyl sulfonyl group, C11 C3 haloalkyl sulfonyl group, cyano group is shown, and 3 is a C2-C6 perfluoroalkyl group, C1-C6 perfluoroa group alkylthio group, C1-C6 perfluoro full O b alkylsulfinyl group, a C1-C6 perf Ruo port alkyl sulfonyl group, Upsilon 2, Upsil
  • ⁇ 6 and ⁇ 9 may be the same or different, and halogen atoms, C 1 -C 4 alkyl groups, C 1 -C 4 haloalkyl groups, C 1 -C 3 alkylthio groups, C 1 -C 3 haloalkylthio groups, C 1-C 3 alkylsulfinyl group, C1- C3 haloalkylsulfinyl group, C1 - C3 alkylsulfonyl group, C1-C3 lambda mouth alkylsulfonyl group, a sheet ⁇ cyano group, Upsilon 8 is C1- C4 haloalkoxy group, C2-C6 par Furuoroarukiru group, C1 - C6 Pas one full O b alkylthio group, C1 --C6 per full O b alkylsulfinyl Finiru group, C1- C6 indicates per full O b alkyl s
  • Qi is a phenyl group
  • halogen atom C1 C4 alkyl group, C1 C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 halo alkenyl group, C2-C4 alkynyl group, C2-C4 C4 alkynyl group, C3-C6 cycloalkyl group, C3-C6 haloalkyl alkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 haloalkylthio group, C1-C3 alkylsulfinyl group, C1-C3 haloalkyl sulfinyl group, C1- C3 alkyl sulfonyl group, C1-C3 double alkyl sulfonyl group, CI- C4 alkyl amino group, di CI-C4 alkyl amino group, cyano group,
  • heterocyclic group is pyridyl group, pyridine one N-hydroxy group, pyrimidinyl group, pyridazyl group, biladyl group, furyl group; chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group , An isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrolyl group, a pyrazolyl group, or a tetrazolyl group).
  • halogen atom C1 C4 alkyl group, C1 C4 haloalkyl group, C2-C4 alkenyl group, C2-C4 haloalkenyl group, C2-C4 alkynyl group, C2-C4 halo alkynyl group, C3-C6 cycloalkyl group C3-C6 halocycloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C3 alkylthio group, C1-C3 octaloalkylthio group, C1-C3 alkylsulfinyl group, CI-C3 haloalkyl sulfinyl group, C1 C3 alkylsulfonyl group, C1 C3 eight-membered alkyl sulfonyl group, C1 C4 alkylamino group, di C1-C4 alkylamino group, cyan
  • L is a halogen atom, a hydroxyl group.
  • X ia , X 2 a, X 3 a, and X 4 a each represent a hydrogen atom, a C 1 -C 3 alkyl group, a trifluoromethyl group, a hydroxy group, an amino group or a halogen atom
  • R a and R b Each represents a fluorine atom or a C 1 -C 4 perfluoroalkyl group
  • R c is hydroxy group
  • one 0- R d R d is CI- C3 alkyl group, C1- C3 haloalkyl group, C1-C3 alkylsulfonyl group, C1-C3 eight necked alkylsulfonyl group, ⁇ Li one Rusuruhoniru group, Alkyl group-C4-C4-C8-eight-alkyl group ⁇ , a chlorine atom, a bromine atom or an iodine atom;
  • R 2 a is a hydrogen atom, C 1 -C 3 alkyl group, C 1 -C 3 haloalkyl group, C 1-C 3 alkoxy group, CI-C 3 haloalkoxy group, C 1 C 4 alkylthio group, C 1-C 4 haloalkylthio group, C 1 C 4 alkyl A C 1 -C 4 haloalkyl group, or
  • Y ia and Y 5 a are each C 1 C 4 alkyl group, C 1 C 4 haloalkyl group, C 1 C 4 alkylthio group, C 1 -C 4 haloalkylthio group, C 1 -C 3 alkylsulfinyl group, C 1 -C 3 haloalkylsulfinyl group, C 1- C3 alkylsulfonyl group, C1 -C3 haloalkylsulfonyl group, cyano group, hydroxy group or halogen atom
  • Y 2 a and Y 4 a each represent a hydrogen atom, a CI-C 4 alkyl group or a halogen atom, and G 2 a represents an oxygen atom or a sulfur atom.
  • J represents a halogen atom or a hydroxy group
  • R c ′ is a hydroxy group, — 0 — Rd (where R d is C1 to C3 alkyl group, C1 to C3 haloalkyl group, C1 to C3 alkylsulfonyl group, C1 to C3 eight-membered alkylsulfonyl A compound represented by formula, arylsulfonyl group, C1-C4 alkyl carbolyl group or C1-C4 eight-membered alkyl group) and a suitable halogenating agent.
  • R ⁇ a shows X2a, X3a, X 4 a, G2a, R2a, Yia, Y2a, Y 4 a, .Ysa, H a, Rb is the same meaning as described in ⁇ Symbol [13]
  • R c represents a chlorine atom, a bromine atom or an iodine atom.
  • X ia , X 2 a, X 3 a and X 4 a each represent a hydrogen atom, a Cl-C 3 alkyl group, a trifluoromethyl group, a hydroxy group, an amino group or a halogen atom
  • R a and R b indicates respectively a fluorine atom or a C1 one C4 Per full O b alkyl group
  • R c is a hydroxy group
  • one 0- R d R d is C1-C3 alkyl group, C1- C3 haloalkyl group, C1-C3 alkylsulfonyl Group, a C1-C3 haloalkylsulfonyl group, an arylsulfonyl group, a C1 C4 alkyl carbonyl group or a C1 C4 haloalkyl group
  • Ria and R 2 a each independently represent a hydrogen atom, C 1 -C 3 alkyl group, Cl-C 3 haloalkyl group, C 1 -C 3 alkoxy group, C 1 -C 3 haloalkoxy group, C 1 -C 4 alkylthio group, C 1 -C 4 valoalkylthio group, C 1 It represents one C4 alkyl group or one C4 C4 alkylcarboyl group,
  • Yia and Y 5 a each represent Cl-C4 alkyl group, Cl-C4.
  • Y 2 a and Y 4 a each represent a hydrogen atom, a C 1 -C 4 alkyl group or a halogen atom, and G 2 a represents an oxygen atom or a sulfur atom.
  • Y ia and Y 5 a are each C 1 C 4 alkyl group, C 1 C 4 haloalkyl group, C 1 -C 4 alkylthio group, C 1 -C 4 octaalkylthio group, C 1 -C 3 alkylsulfinyl group, C 1 -C 3 haloalkylsulfinyl group, C 1 -C3 alkylsulfonyl group, C1 -C3 haloalkylsulfonyl group, cyano group, hydroxy group or halogen atom
  • y 2 a and Y 4 a each represent a hydrogen atom, C 1 C 4 alkyl group or a halogen atom, and • G 2 a represents an oxygen atom or a sulfur atom)
  • H c ' is Hydroxy group
  • 1-l Rd is a CI-C3 alkyl group, C1-C3 haloalkyl group, C1-C3 alkyl sulfonyl group, C1-C3 eight-membered alkyl sulfonyl group, aralyl sulfonyl group, C1-C4 alkyl group Or represents a C1 to C4 haloalkyl group.
  • R c ′ represents a chlorine atom, a bromine atom or an iodine atom.
  • X ia , X 2 a, X 3 a and X 4 a each represent a hydrogen atom, a Cl—C 3 alkyl group, a trifluoromethyl group, a hydroxy group, an amino group or a halogen atom
  • R a and R b Each represents a fluorine atom or a C1 C4 perfluoroalkyl group
  • R c is a hydroxy group
  • -0-R d R d is a C1 C3 alkyl group, a C1 C3 haloalkyl group, a C1-C3 alkyl sulfonyl Group, C1-C3 eight-membered alkylsulfonyl group, arylsulfonyl group, C1-C4 alkyl group or C1-C4 eight-membered alkyl group
  • chlorine atom bromine atom or iodine atom
  • Ria and a each represent a hydrogen atom, C1 -C3 alkyl group, C1 -C3 haloalkyl group, C1-C3 alkoxy group, C1-C3 haloalkoxy group, C1-C4 alkylthio group, C1-C4 haloalkylthio group, C1-C4 Alkyl group, or C1-C4 alkyl alkyl group;
  • Yia and Y 5 a each represent a C 1 C 4 alkyl group, a Cl 1 C 4 haloalkyl group, a C 1 -C 4 alkylthio group, a C 1 -C 4 octaalkylthio group, a C 1 -C 3 alkylsulfinyl group, a C 1 -C 3 haloalkylsulfinyl group, C 1- A C3 alkylsulfonyl group, a C1 -C3 haloalkylsulfonyl group, a cyano group, a hydroxy group or a halogen atom;
  • Y 2 a and Y 4 a each represent a hydrogen atom, a C 1 -C 4 alkyl group or a hydrogen atom, Gia and G 2 a each represent an oxygen atom or a sulfur atom,
  • Qia is a phenyl group
  • heterocyclic group means pyridyl group, pyridine-N-oxide group, pyrimidinyl group, pyridazyl group, biladyl group, furyl group, chenyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, An isothiazolyl group, an imidazolyl group, a triazolyl group, a pyrrole group, a pyrazolyl group or a tetrazolyl group);
  • J ′ represents a halogen atom or a hydroxy group
  • J ′ ′ represents a halogen atom or a hydroxy group
  • R c ' is hydroxy group, - 0-: R d (R d are C1 -C3 alkyl groups, C1-C3 haloalkyl groups, C1-C3 alkylsulfonyl groups, C1 -C3 haloalkylsulfonyl group, ⁇ Li one Rusuruhoniru groups, C1 -C4 alkyl carpenyl group or C1-C4 eight-membered alkyl carboyl group is shown.
  • a compound represented by the formula: and a suitable halogenating agent A compound represented by the formula: and a suitable halogenating agent.
  • [29] A mixture obtained by combining the compound according to the above [1] to [8] with one or more other insecticides and Z or a fungicide.
  • the compound of the present invention exhibits excellent control effect as an insecticide at a low dose, and other insecticides, acaricides, nematocides, fungicides, herbicides, plant growth regulators, biological pesticides, etc. Even when used in combination with this, it exhibits excellent control effects.
  • BEST MODE FOR CARRYING OUT THE INVENTION The terms used in the general formula such as the general formula (1) of the present invention have the meanings as described below in their definitions.
  • the "eight rogen atom” represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • Ca—Cb (a, b represents an integer of 1 or more)” means, for example, “C1—C3” means that the number of carbon atoms is 1 to 3, “C2—C6 “” Means that the number of carbon atoms is 2 to 6, and “C1-C4" means that the number of carbon atoms is 1 to 4 ".
  • N _ means normal, "i one” means iso, "s-" means secondary one, and "t-” means evening shaly.
  • the “optionally substituted alkyl group” is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1 C6 alkoxy group, a CI-C6 haloalkoxy group, a C1 C6 alkylthio group, a C1 C6 haloalkylthio group, C1 C6 alkyl sulf Cinyl group, C1 C6 haloalkyl sulfinyl group, C1 C6 alkyl sulfonyl group, C1 C6 haloalkyl sulfonyl group, C1-C6 alkyl carbonyl group, C1-C6 halo alkyl caronyl group, C1 C6 alkoxycarbonyl group, C1-C6 Haloalkoxy carboxyl group, C 1 C 6 alkyl alkyl group, C 1 -C 6 haloalkyl carboxyl
  • the “optionally substituted C 1 -C 4 alkyl carbonyl group” is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C 1 C 6 alkoxy group, a C 1 -C 6 haloalkoxy group, a CI-C 6 alkylthio Group, C 1 C 6 haloalkylthio group, C 1 C 6 alkylsulfinyl group, C 1 C 6 haloalkylsulfinyl group, C 1 -C 6 alkylsulfonyl group, CI-C 6 haloalkylsulfonyl group, C 1 C 6 alkyl carbonyl group, C 1 -C 6 octaalkyl Carponyl group, CI-C6 alkoxy group, CI-C6 haloalkoxy carbonyl group, CI-C6 alkyl carboyloxy group, C1 C6
  • the “optionally substituted phenyl group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1 C6 alkoxy group, a C1 to C6 haloalkoxy group, CI — C6 alkylthio group, C 1 C 6 haloalkylthio group, C 1 C 6 alkylsulfinyl group, C 1 — C 6 eight-membered alkylsulfinyl group, C 1 — C 6 alkylsulfonyl group, C 1 C 6 haloalkylsulfonyl group, C 1 C 6 alkyl carpolyl Group, C1 C6 eight-membered alkyl carbonyl group, C1-C6 alkoxy carbonyl group, C1 C6 two-membered alkoxycarbonyl group, CI-C6 alkyl carbyloxy group, C1
  • the “optionally substituted naphthyl group” may be the same or different, and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a C1 C6 alkoxy group, a C1 C6 haloalkoxy group, C1 C6 alkylthio group, C1-C6 haloalkylthio group, C1 C6 alkylsulfinyl group, C1 C6 octaloalkylsulfinyl group, C1 C6 alkylsulfonyl group, C1 C6 haloalkylsulfonyl group, C1 C6 alkyl Carbonyl group, C 1 -C 6 haloalkyl carboxyl group, C 1 C 6 alkoxy carbonyl group, C 1 C 6 eight-membered alkoxy carbonyl group, CI-C 6 alkyl carboxyloxy group, C 1-C 6 haloal
  • the “optionally substituted heterocyclic group” may be the same or different and is a hydrogen atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, a 'C1 C6 alkoxy group, a C1 C6 halo Alkoxy group, C 1 C 6 alkylthio group, C 1 C 6 haloalkylthio group, C 1 C 6 alkylsulfinyl group, C 1 -C 6 haloalkylsulfinyl group, C 1 C 6 alkylsulfonyl group, C 1 C 6 haloalkylsulfonyl group, C 1 -C 6 alkylcarbonyl group , C1-C6 haloalkyl group, C1 C6 alkoxy carbonyl group, C1 C6 haloalkoxy carbonyl group, C1 C6 alkyl group alkyloxy group, C1-C6 haloalkyl s
  • C.sub.1 C.sub.3 alkyl group means, for example, linear or branched C.sub.1 to C.sub.3 carbon atoms such as methyl, ethyl, n-propyl, i-propyl and cyclopropyl.
  • C1-C4 alkyl group means, in addition to “C1-C3 alkyl group”, for example, linear or branched chains such as n-butyl, s-peptyl, i-butyl, t-butyl and the like.
  • C1-C4 alkyl group and the "C.sub.1 C.sub.6 alkyl group” means, for example, n-pentyl, 2-pentyl, 3-pentyl, neopentyl, in addition to "C.sub.1-C.sub.4 alkyl group".
  • n represents a linear or branched alkyl group having 1 to 6 carbon atoms, such as n-hexyl, 2-hexyl, 4-methyl-2-pentyl, 3-methyl-n-pentyl, etc.
  • C.sub.1 C.sub.3 fluoroalkyl group examples include monofluoromethyl, difluoromethyl, trifluoromethyl, monochloromethyl, dichloromethyl, trichloromethyl, trichloromethyl, monobromomethyl, dibromomethyl, tribromomethyl, 1 fluoroe.
  • C 2 -C 4 alkenyl group is, for example, an alkenyl group having 2 to 4 carbon atoms having a double bond in a carbon chain such as vinyl, aryl, 2-butenyl, 3-butenyl and the like, “C2- The term "C4 haloalkenyl group” means, for example, 3, 3-difluoro-2- Propenyl, 3, 3-dichloro-2-propenyl, 3, 3-di-bimodal 2-propenyl, 2, 3-di-bimodal 2-propenyl, 4, 4-difluoro- 3-buteni
  • C 2 _C 4 alkynyl group means, for example, a linear or branched carbon atom having a triple bond in a carbon chain such as propargyl, 1-butyne-13-yl, 1-butyne-1-3-methyl-3-yl, etc.
  • C 2 -C 4 haloalkinyl group means, for example, a triple bond in a carbon chain substituted by one or more halogen atoms which may be the same or different. Represents a linear or branched alkenyl group having 2 to 4 carbon atoms,
  • C3-C6 cycloalkyl group is, for example, a cycloalkyl group having 3 to 6 carbon atoms having a cyclic structure such as cyclopropyl, cyclobutyl, cyclopentyl, 2-methylcyclopentyl, 3-methylcyclopentyl, cyclohexyl and the like.
  • C 3 -C 6 halocyclyl alkyl group means, for example, one or more of 2, 2, 3, 3-tetrafluorocyclobutyl, 2-chlorocyclohexyl, 4-chlorocyclohexyl and the like.
  • C 1 C 3 alkoxy group is, for example, linear or branched C 1 -C 3 alkoxy group such as methoxy, ethoxy, n-propyloxy, isopropyloxy, etc.
  • C 3 haloalkoxy group is, for example, trifluoromethyl, 1, 1, 1, 3, 3 or 3 hexafluoro- 2-propyloxy, 2, 2, 2-trifluoroethoxy, 2-chloroethoxy, 3-
  • C 4 haloalkoxy group means, in addition to “C 1 -C 3 haloalkoxy group”, for example, 1, 1, 1, 3, 3, 4, 4, 4-Octafluoro-2 and 2-butyloxy etc. same or different 1 or more Represents a linear or branched haloalkoxy group such
  • C 1 -C 3 alkylthio group is, for example, methylthio, acetylthio, n-pro A linear or branched C13 alkylthio group such as pylthio, i-propylthio, cyclopropylthio etc.
  • C1 C4 alkylthio group is added to "C1 C3 alkylthio group”
  • a linear or branched alkylthio group having 14 carbon atoms such as n-butylthio, i-heptylthio, s-butylthio, t-heptylthio, cyclopropylmethylthio, etc.
  • C 1 _C 3 haloalkyl is, for example, the same or different as trifluoromethylthio, pentafluorothiolthio, 2,2,2-trifluorofluorothiolthio, heptafluoro-n-propylthio, heterofluoro-i-propylthio, etc.
  • a linear or branched C 13 alkylthio group substituted by one or more halogen atoms which may be In addition to the "C1-C3 eight-membered alkylthio group", the C4 haloalkylthio group may be, for example, nonafluoro-n-butylthio, nonafluoro-s-butylthio, 44,4 _ trifluorinated n, or the same or different Good number of linear or branched carbon atoms substituted by one or more halogen atoms:! To 4 alkylthio groups,
  • C.sub.1 C.sub.3 alkylsulfinyl group examples include linear or branched C.sub.13 carbon atoms, such as methylsulfinyl, phenylsulfinyl, n-propylsulfinyl, i-propylsulfinyl, cyclic propylsulfinyl and the like.
  • Alkylsulfinyl group and examples of “C.sub.1 C.sub.3 C.sub.3 haloalkylsulfinyl group” are, for example, trifluoromethylsulfinyl, pentafluoroethenylsulfinyl, 2.sup.2, 2-trifluoroethenylsulfinyl, and heptafluoro-n.
  • C1-C3 alkylsulfonyl group examples include linear or branched alkyl sulfo having 13 carbon atoms, such as methylsulfonyl, phenylsulfonyl, n-propylsulfonyl, i-propylsulfonyl, cyclopropylsulfonyl and the like.
  • C 1 -C 3 haloalkyl sulfonyl group means, for example, trifluoro methyl sulfonyl, peneful fluoroethyl sulfonyl, 2, 2 2-trifluroethyl sulfonyl, hepta fluoro- n-propyl sulfonyl, heptovyl
  • isopropylsulfonyl A linear or branched C 1 -C 3 alkylsulfonyl group substituted by a halogen atom,
  • arylsulfonyl group is, for example, an aromatic ring such as phenylsulfonyl, p-toluenesulfonyl, mononaphthylsulfonyl, 2-naphthylsulfonyl, anthrylsulfonyl, fuenanthrylsulfonyl, fastenarylsulfonyl, etc. And have 6 to 14 arylsulfonyl groups having 6 to 14 carbon atoms,
  • C.sub.1 C.sub.4 alkylamino group examples include, for example, linear or branched or cyclic C.sub.1 to C.sub.4 carbon atoms, such as methylamino, dimethylamino, n-propylamino, i-propylamino, n-single-pylamino, cyclopropylamino, etc.
  • "Di-Ci-C4 alkylamino group” means, for example, linear or branched which may be the same or different, such as dimethylamino, diethyl ⁇ / amino, N-ethyl N-methylamino, etc.
  • a chain-like amino group having 1 to 4 carbon atoms and substituted by two alkyl groups,
  • C 1 _C 4 alkylcarbonyl group examples include linear or branched or cyclic alkyl groups having 1 to 4 carbon atoms, such as formyl, acetyl, propionyl, isopropylcarbonyl, cyclopropylcarbonyl and the like.
  • C.sub.1 C.sub.4 haloalkylcarbonyl group examples include, for example, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chloroacetyl, dichloroacetyl, trichloroacetyl, bromoacetyl, iodoacetyl, 3, 3, 3-trifluoropropionyl, 2, 2
  • C 1 -C 4 alkylcarbonyloxy group represents, for example, a linear or branched alkyl C 1 -C 4 alkyl group such as acetyloxy and propionioxyl, and
  • C.sub.1 C.sub.4 alkoxy carbonyl group examples include linear or branched C.sub.1-C.sub.4 alkoxy group such as methoxycarponyl, etoxycarponil, isopropyloxy carponil and the like. Shown,
  • C.sub.1 C.sub.4 perfluoroalkyl group examples include trifluoromethyl, penulor fluorol, hepter fluoro-n-propyl, hepper fluoro i-pro A linear or branched alkyl group having 1 to 4 carbon atoms, all substituted by a fluorine atom such as pill, nonafluoro-n-butyl, nonafluoro-2-butyl, and nonafluoro-i monobutyl;
  • C6 perfluoroalkyl group examples include pentofluorene, heptafluoro-n-propyl, heptafluoro-i-i-propyl, nonafluoro-n-butyl, nonafluoro- 2-butyl, nonafluoro-i-butyl, perfluoro-n-pentyl, Represents a linear or branched alkyl group having 2 to 6 carbon atoms, which is
  • C1-C6 perfluoroalkylthio group examples include trifluoromethylthio, pentylenefluorthio, heptafluoro-n-propylthio, heptafluorinated i-propylthio, nonafluoro- n-butylthio, nonafluoro-2- And represents a linear or branched alkylthio group having 1 to 6 carbon atoms, which is all substituted by a fluorine atom such as tylthio, nonafluoro-butylthio, perfluoro-n-pentylthio, perfluoro-n-hexylthio, etc.
  • C1-C6 perfluoroalkylsulfinyl group examples include: trifluorome cillesulphinyl, penhyol fluoroethylsulfinyl, heptafluoro- n-propylsulfinyl, heptafluoro-i monopropylsulfinyl, nonafluoro n-butyl A linear or branched C 1 -C 6 carbon atom all substituted by a fluorine atom such as sulfinyl, nonafluoro-2-butylsulfinyl, nonafluoro-butylsulfinyl, perfluoro-n-pentylsulfinyl, perfluoro-n-hexylsulfinyl and the like Indicating alkylsulfinyl groups,
  • C.sub.1 C.sub.6 perfluoroalkylsulfonyl group are, for example, trifluoromethylsulfonyl, penuvol fluoroethersulfonyl, heptafluoro-n-propylsulfonyl, heptafluoro-i-propylsulfonyl, nonafluoro-n-butyl Sulfonyl, nonafluoro-2-butylsulfonyl, nonafluoro-i-butylsulfonyl, perfluoro-n-pentylsulfonyl, perfluoro-n-monoalkylsulfonyl and the like, the number of linear or branched carbon atoms all substituted with a fluorine atom 1 to 6 alkyl sulfonyl groups are shown.
  • the compound represented by the general formula (1) of the present invention may contain one or more asymmetric carbon atoms or asymmetric centers in its structural formula, and two or more optical isomers may be contained.
  • the present invention includes all of each optical isomer and a mixture containing them in any ratio.
  • the compound represented by the general formula (1) of the present invention there may be a case where two or more kinds of geometrical isomers derived from a carbon-carbon double bond may exist in the structural formula. Is intended to encompass all geometric isomers of each and mixtures in which they are contained in any proportion.
  • Preferred substituents or atoms for the substituent etc. in the compound represented by the general formula (1) etc. of the present invention are as follows. '
  • ⁇ is a carbon atom, a nitrogen atom or an oxidized nitrogen atom and, simultaneously, A 2 , A 3 and A 4 are all carbon atoms, more preferably , Ai, A 2 , A 3 and A 4 are all carbon atoms.
  • R] _ is preferably a hydrogen atom or a CI-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or a acetyl group.
  • R 2 is preferably a hydrogen atom or a CI-C 4 alkyl group, and more preferably a hydrogen atom, a methyl group or a methyl group.
  • X is preferably a hydrogen atom or a halogen atom, more preferably a hydrogen atom or a fluorine atom.
  • n is 0, 1, or 2, more preferably 0 or 1.
  • X is preferably a hydrogen atom or a halogen atom, and more preferably a hydrogen atom or a fluorine atom.
  • x 2 is a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
  • Preferred as X 3 and X 4 is a hydrogen atom.
  • G represents a phenyl group, a halogen atom, a C1 C4 alkyl group, a C1 C4 haloalkyl group, a C2-C4 alkenyl group, a C2-C4 haloalkenyl group, a C2-C4 alkynyl group, a C2-C4 haloalkynyl.
  • Q 2 is a substituted phenyl group or a substituted pyridyl group represented by the general formula (2) or the general formula (3), and ',
  • Yi and Y 5 are chlorine atom, bromine atom, iodine atom, methyl group, acetyl group, ⁇ -propyl group, i-propyl group, n-butyl group, 2-butyl group, trifluoro A methyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluorinated methylsulfonyl group, a cyano group,
  • ⁇ 2 , ⁇ ⁇ ⁇ 4 and ⁇ 7 preferred is a hydrogen atom, a halogen atom or a methyl group, and further preferred is a hydrogen atom,
  • Y 8 preferably, pentuol fluoroeyl group, heptane fluoro- —-propyl group, heptane fluoro-i-propyl group, nonafluoro- n-butyl group, nonaf Ruoro 2-butyl group, nonafluoro-1 butyl group, trifluoro methylthio group, peneful fluorothiolthio group, heptafluoro-n-propylthio group, heptafluoro-i-propylthio group, nonafluoro-'n-peptylo group, nonafluro 2-butylthio group, trifluoromethylsulfinyl group, phenylfluorophenyl sulfinyl group, heptafluoro- n-propylsulfinyl group, heptafluoro-i-propylsulfinyl group, monoprop
  • L is a chlorine atom, a bromine atom or a hydroxy group.
  • R ia is preferably a hydrogen atom or a C 1 -C 4 alkyl group, more preferably a hydrogen atom, a methyl group or a acetyl group.
  • a is preferably a hydrogen atom or a CI-C4 alkyl group, and more preferably a hydrogen atom, a methyl group or a methyl group.
  • Each of Gia and G 2 a is preferably an oxygen atom or a sulfur atom, and further preferably both of G ia and G 2 a are an oxygen atom.
  • Xia are a hydrogen atom and a halogen atom, and more preferably a hydrogen atom or a fluorine atom.
  • Preferred as X 2 a is a hydrogen atom or a fluorine atom, and more preferably a hydrogen atom.
  • Preferred as X 3 a and X 4 a is a hydrogen atom.
  • Y ia and Y 5 a are preferably a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an i-propyl group, an n-butyl group, a 2-butyl group, a triful And an trifluoromethyl group, a methylthio group, a methylsulfinyl group, a methylsulfonyl group, a trifluoromethylthio group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, and a cyano group.
  • Y 2 a and Y 4 a preferred are a hydrogen atom, a halogen atom, and a methyl group, and more preferred is a hydrogen atom.
  • Rb is preferably a 'fluorine atom, a trifluoromethyl group, a pentafluoro group, or a heptafluorinated n-propyl group, and more preferably a fluorine atom or a trifluoromethyl group, respectively.
  • the group is Penn Fluo Roetyl.
  • R c is a hydroxy group, a chlorine atom, a 'bromine atom, an iodine atom, a methoxy group, an ethoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonioxy group, a phenylsulfonyloxy group, a p- It is a toluenesulfonyloxy group, an acetoxy group, a trifluoroacetoxy group, and more preferably a hydroxy group, a chlorine atom, a bromine atom, a methoxy group, a methylsulfonyloxy group, a trifluoromethylsulfonyloxy group, And an enylsulfonyloxy group or a p-toluenesulfonyloxy group, more preferably a hydroxy group, a chlorine atom or a bromine atom.
  • R c is a hydroxy group.
  • R c is a chlorine atom or a bromine atom.
  • Each of J, J 'and J is preferably a hydroxy group, a chlorine atom or a bromine atom, and more preferably a chlorine atom.
  • Q 2 has the meaning described in [1] or the general formula (2)
  • any solvent which does not significantly inhibit the progress of the reaction may be used.
  • aromatic hydrocarbons such as water, benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and the like
  • Linear or cyclic ethers such as 1, 2-dimethoxy aetan, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, acetone Ketones such as methyl isobutyl ketone and cyclohexanone, amides such as dimethylformamide and dimethylacetamide, ditolyls such as acetonilyl, and inert solvents such as 1, 3-dimethyl-2- imidazolidinone
  • solvents may be used alone or in combination of two or more. Can be used.
  • a base it is triethylamine, tri_ n- peptylamine, a pyridine, Organic bases such as 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, carbonates such as sodium hydrogencarbonate and potassium carbonate, dipotassium monohydrogenphosphate, phosphoric acid It is possible to show phosphates such as trisodium, alkali metal hydrides such as sodium hydride, alkali metal alkoxides such as sodium methoxide and sodium sulfate, and the like. These bases may be suitably selected and used in the range of 0.01 to 5 times the molar equivalent with respect to the compound represented by the general formula (19).
  • the reaction temperature may be appropriately selected in the range of, for example, 120 ° C. to the reflux temperature of the solvent to be used, and the reaction time may be from several minutes to 96 hours.
  • the aromatic carboxylic acid halide derivative can be easily produced from the aromatic carboxylic acid by a conventional method using a halogenating agent.
  • a halogenating agent for example, a halogenating agent such as thionyl chloride, thionyl bromide, oxyphosphorous chloride, oxalyl chloride, phosphorous trichloride and the like can be mentioned.
  • the compound represented by the general formula (21) from the compound represented by the m-nitro aromatic carboxylic acid derivative and the general formula (20) without using an oculogenating agent.
  • an additive such as 1-hydroxybenzotriazole is appropriately used according to the method described in Ch. Em. Ber. 788 (1997), N, N ' It is possible to show a method of using a condensing agent which uses a dicyclohexylcarboximide.
  • condensing agents to be used in this case 1-ethyl 3- (3-dimethylaminopropyl) carpimide, 1,1 monopolaryl bis (1-H) -imidazole and the like can be shown.
  • reaction temperature is not limited, and an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate.
  • the reaction temperature and reaction time may be appropriately selected according to the progress of the reaction.
  • the aromatic carboxylic acid amide derivative having a nitro group represented by the general formula (21) can be converted to an aromatic carboxylic acid amide derivative having an amino group represented by the general formula (22) by a reduction reaction.
  • the reduction reaction include a method using a hydrogenation reaction and a method using a metal compound (eg, stannous chloride (anhydride), iron powder, zinc powder, etc.).
  • the reaction can be carried out in a suitable solvent, in the presence of a catalyst, under normal pressure or pressure, and in a hydrogen atmosphere.
  • a catalyst include: 'Palladium-based catalysts such as palladium, nickel catalysts such as Raney nickel, cobalt catalysts, ruthenium catalysts, rhodium catalysts, platinum catalysts, etc.
  • solvents include water, methanol, ethanol etc. Alcohols, aromatic hydrocarbons such as benzene and toluene, linear or cyclic ethers such as ether, dioxane and tetrahydrofuran, and esters such as ethyl acetate can be shown.
  • the pressure may be 0.1 to 10 M Pa
  • the reaction temperature may be 120 ° C. to the reflux temperature of the solvent used
  • the reaction time may be appropriately selected from several minutes to 96 hours, respectively, and the general formula (22) Can be produced efficiently.
  • any solvent which does not significantly inhibit the progress of this reaction may be used, for example, Water, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, etc.
  • Chains such as cetyl ether, dioxane, tetrahydrofuran and 1,2-dimethyshetan Or cyclic ethers, esters such as ethyl acetate and butyl acetate, alcohols such as methanol and ethanol, acetone, ketones such as methyl isopyl ketone and cyclohexane, dimethylformamide, dimethylacetoamide and the like
  • inert solvents such as 1,3-dimethyl-2-imidazolidinone. These solvents may be used alone or in combination of two or more. ,
  • organic bases such as triethylamine, tri-n-peptylamine, pyridine, 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, sodium hydrogencarbonate and potassium carbonate Indicates carbonates, phosphates such as dipotassium monohydrogen phosphate, trisodium phosphate, alkali metal hydrides such as sodium hydride, alkali metal alcoholates such as sodium methoxide, sodium ethoxide, etc. be able to'.
  • These bases may be appropriately selected and used in the range of 0.01 to 5 times the molar equivalent with respect to the compound represented by the general formula (2 2).
  • the reaction temperature may be appropriately selected from the range of several minutes to 96 hours, and the reaction temperature and the reflux temperature of the solvent to be used may be respectively selected from several minutes to 96 hours. It is also possible to produce the method using the condensing agent described in 1 (i) or the mixed acid anhydride method.
  • a compound represented by the general formula (2 8) is sulfonyl chloride, oxalyl chloride, phosgene, phosphorus oxychloride, phosphorus pentachloride, phosphorus trichloride, thionyl bromide, phosphorus tribromide, getilaminosulfur trifluoride, etc.
  • the compound represented by General formula (29) can be manufactured by the well-known conventional method of making it react.
  • ammonia is used to carry out the amination reaction according to the conditions described in J. Org. Chem. Page 1958 (1958) to produce the compound represented by the general formula (38)
  • conditions such as the reaction solvent are not limited to those described in the literature, an inert solvent that does not significantly inhibit the progress of the reaction may be used as appropriate. Depending on the progress of the reaction, it may be selected appropriately.
  • ammonia methylamine, phenylalanine, etc. can also be shown as the aminating agent.
  • R 2 is as defined above, Yi, respectively Y 5 represents a methyl group, a chlorine atom, a bromine atom, an iodine atom, ⁇ 2, ⁇ 4 have the same meanings as defined above, R f Represents a CI-C6 perfluoroalkyl group, m represents 1, 2)
  • the compound of general formula (42) can be produced by reacting
  • haloalkyl iodides represented by the general formula (41) include, for example, trifluoromethyl iodide, chloroformated fluorethiol, iodided iodide fluoro-n-pyl pill, iodide iodide heptane-fluoroisopropyl, iodide It is possible to show nonafluoro-n-butyl, nonafluoro-2-butyl iodide and the like, which may be suitably used in the range of 1 to 10 times molar equivalent with respect to the compound represented by the general formula (40).
  • the solvent used in this step is not limited to the solvents described in the above-mentioned documents, and as the solvent, any solvent which does not significantly inhibit the progress of the reaction may be used.
  • Aromatic hydrocarbons such as toluene, toluene and xylene, Halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc.
  • Chains such as jetyl ether, dioxane, tetrahydrofuran and 1, 2-dimethoxyethane Or cyclic ethers, esters such as ethyl acetate and butyl acetate, tonnes such as methanol and ethanol, amides such as dimethylformamide and dimethylacetoamide, nitriles such as acetyl ditrile, 1,3-dimethyl-2 Inert solvents such as monoimidazolidinone and hexamethyl phosphate triamide can be used, and these solvents can be used alone or in combination of two or more. In particular, polar solvents are preferred.
  • the reaction temperature may be appropriately selected within the range of several minutes to 96 hours, for example, at a temperature of 20 ° C. to the reflux temperature of the solvent used.
  • a compound represented by the general formula (43) can be produced, for example, Synth. Co mm un. 1 2 6 1 (1 899) The method described in can be shown.
  • halogenating agent for example, chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, and N-succinimide can be shown, and these are represented by the general formula (4 2) It may be suitably used in the range of 1 to 10 times molar equivalent with respect to the compound to be
  • the solvent used is not limited to the solvents described in the above-mentioned documents, and the solvent may be any solvent that does not significantly inhibit the progress of the reaction.
  • aromatic hydrocarbons such as water, benzene, toluene, xylene, etc.
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc.
  • gethyl ether dioxane, tetrahydrofuran
  • 2- Linear or cyclic ethers such as dimethoxyethane, esters such as ethyl acetate and butyl acetate
  • alcohols such as methanol and ethanol
  • ketones such as acetone, methyl isopyl ketone and cyclohexanone
  • dimethyl formamide Amides such as dimethylacetoamide, and tolylols such as acetonitrile, 1, 3-Dimethyl-2-imidazolid
  • reaction temperature may be appropriately selected in the range of ⁇ 20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours.
  • the compound represented by the general formula (44) can be produced by using an appropriate oxidizing agent, for example, the method described on page 4955 (19.94). Can be shown.
  • oxidizing agent examples include organic peracids such as m-clear perbenzoic acid, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, nitrogen dioxide, nitrous acid nitrate, iodine, bromine, N-Bromosuccinimide, sodium dodecyl benzyl, hypochlorous acid! : One butyl etc. can be shown.
  • organic peracids such as m-clear perbenzoic acid, sodium metaperiodate, hydrogen peroxide, ozone, selenium dioxide, chromic acid, nitrogen dioxide, nitrous acid nitrate, iodine, bromine, N-Bromosuccinimide, sodium dodecyl benzyl, hypochlorous acid! : One butyl etc. can be shown.
  • the solvent used in this step is not limited to the solvents described in the above-mentioned documents, and any solvent may be used as long as it does not significantly inhibit the progress of the reaction, and these solvents may be used alone or in combination of two or more. Can be used. In particular, polar solvents are preferred.
  • the reaction temperature may be appropriately selected in the range of, for example, 120 ° C. to the reflux temperature of the solvent used, and the reaction time may be from several minutes to 96 hours.
  • ananilin derivative represented by the general formula (47) can be produced according to the production method 6, and it is further shown in the present invention
  • the compound of the present invention can be produced by appropriately selecting the production method. , Manufacturing method 8
  • the compound represented by the general formula (4 8) is suitably selected
  • the compound represented by the general formula (49) can be produced by reaction with a suitable reactant using a suitable base in a suitable solvent.
  • any solvent which does not significantly inhibit the progress of this reaction may be used.
  • aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane
  • aromatic hydrocarbons such as benzene, xylene and toluene
  • Dichloromethane, chloroform, carbon tetrachloride, halogenated hydrocarbons such as 1,2-dichloromethane, diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane Ethers such as dimethylformamide, amides such as dimethylformamide, dimethylacetoamide, acetonitrile, nitriles such as propioditolyl, acetone, ketones such as methyl isobutyl ketone, cyclohexanone and methylethyl ketone, cetyl acetate And esters such as butyl acetate, alcohols such as butyl
  • the base examples include organic bases such as triethylamine, triptylamine, pyridine and 4-dimethylaminopyridine, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, and carbonates such as sodium hydrogencarbonate and potassium carbonate. , Potassium monohydrogen phosphate, trisodium phosphate etc. ⁇ Phosphate salts, Alkali metal hydride salts such as sodium hydride hydrogenated, Alkali metal alkoxides such as sodium methoxide, sodium ethoxide etc., ⁇ -butyllithium Etc., and Grignard reagents such as diethylmagnesium bromide. These bases may be appropriately selected or used as a solvent in the range of 0.01 to 5 molar equivalents with respect to the compound represented by the general formula (48).
  • organic bases such as triethylamine, triptylamine, pyridine and 4-dimethylaminopyridine
  • alkyl halides such as methyl iodide, brominated ethyl bromide, trifluoromethyl iodide, and 2, 2, 2-trifluorethoyl iodide, halogenated aryls such as sulfonyl halide
  • halogenated propargyls such as propargyl bromide
  • halogenated acyls such as acetyl chloride
  • acid anhydrides such as trifluoroacetic acid anhydride
  • alkyl sulfuric acids such as dimethyl sulfuric acid and jetyl sulfuric acid.
  • These reactive agents may be appropriately selected within the range of 1 to 5 times the molar equivalent with respect to the compound represented by the general formula (48), or may be used as a solvent.
  • the reaction temperature may be appropriately selected within the range of from 180 ° C. to the reflux temperature of the solvent used, and the reaction time may be from several minutes to 96 hours.
  • the compound represented by the general formula (22) is reacted with an aldehyde or a cane in a suitable solvent, a suitable catalyst is added, and reaction is performed under a hydrogen atmosphere to obtain a compound represented by the general formula (50 The compound represented by these can be manufactured.
  • the solvent may be any solvent which does not significantly inhibit the progress of the reaction, and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane, and aromatic hydrocarbons such as benzene, xylene and toluene.
  • halogenated hydrocarbons such as 1,2-dichloroethane, diethyl ether, dioxane, ethers such as tetrahydrofuran, 1,2-dimethoxyethane, dimethyl formamide, dimethyl acetamide 1, amides such as acetoamide, acetonitrile, nitriles such as prop
  • esters such as acetyl acetate, butyl acetate, 1, 3- Dimethyl- 2-imidazolidinone, Solvents such as sulfolane, dimethyl sulfoxide, alcohols such as methanol and ethanol, water, etc. can be shown, and these solvents can be used alone or in combination of two or more.
  • palladium catalysts such as palladium-carbon and palladium hydroxide-carbon
  • nickel catalysts such as Raney nickel
  • cobalt catalysts platinum catalysts
  • ruthenium catalysts rhodium catalysts and the like
  • aldehydes examples include aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetoaldehyde, difluoroacetoaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetoaldehyde, trichloroacetoaldehyde and promoacetaldehyde.
  • aldehydes such as formaldehyde, acetoaldehyde, propionaldehyde, trifluoroacetoaldehyde, difluoroacetoaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetoaldehyde, trichloroacetoaldehyde and promoacetaldehyde.
  • ketones examples include ketones such as acetone, perfluoroacetone, and methyl ketone.
  • the reaction pressure may be appropriately selected in the range of 1 atm to 100 atm respectively.
  • the reaction temperature may be appropriately selected from a range of from 20 ° C. to the reflux temperature of the solvent used, and the reaction time may be in the range of several minutes to 96 hours.
  • a compound represented by the general formula (50) is produced by reacting a compound represented by the general formula (22) with an aldehyde or ketone in a suitable solvent and treating an appropriate reducing agent. Compounds can be produced.
  • any solvent which does not significantly inhibit the progress of the reaction may be used.
  • aliphatic hydrocarbons such as hexane, cyclohexane, methyl sulfoxide and the like, aromatic carbons such as benzene, xylene, toluene and the like Hydrogens, Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-Dichloroethane, etc., Ethers such as diethyl ether, Dioxane, Tetrahydrofuran, 1, 2-Dimethoxyethane, Dimethylformi Amides, amides such as dimethylacetoamide, acetonitrile, nitriles such as propioditolyl, acetone, ketones such as methyl isobutyl ketone, cyclohexanone, methyl ethyl ketone, etc.
  • esters such as ethyl acetate, butyl acetate, etc. 1, 3-Dimethyl-2-imidazolidinone, Ruhoran, dimethyl sulfoxide, methanol, alcohol such as ethanol, a solvent such as water can show, these solvents may be used alone or as a mixture of two or more.
  • polohydrides such as sodium polo hydride, sodium sian polo hydride, Sodium triacetate polo hydride and the like.
  • aldehydes include formaldehyde, acetaldehyde, propionaldehyde, trifluoroacetoaldehyde, difluoroacetoaldehyde, fluoroacetaldehyde, chloroacetaldehyde, dichloroacetoaldehyde, trichloroacetoaldehyde, promoacetaldehyde and the like.
  • ketones include ketones such as acetone, perfluoroacetone, and methyl ketone.
  • the reaction temperature may be appropriately selected within the range of from 100 ° C. to the reflux temperature of the solvent used, and the reaction time may be from several minutes to 96 hours, respectively.
  • the compound represented by the general formula (2 2.) is reacted with a formylating agent in a suitable solvent or in the absence of a solvent, and a suitable reducing agent is treated to obtain Ri in the general formula (50) ′.
  • a suitable reducing agent is treated to obtain Ri in the general formula (50) ′.
  • Compounds that are methyl groups can be prepared.
  • any solvent which does not significantly inhibit the progress of the reaction may be used.
  • aliphatic hydrocarbons such as hexane, cyclohexane, methyl sulfoxide and the like, aromatic carbons such as benzene, xylene, toluene and the like Hydrogens, Dichloromethane, Chloroform, Carbon tetrachloride, Halogenated hydrocarbons such as 1,2-dichloroethane, diethyl ether, Dioxane, Ether hydrofuran, Ethers such as 1,2-Dimethoxyethane, Dimethyl ether Amides such as formiamide, dimethylacetoamide, nitriles such as acetonitrile, propionitrile, acetones, ketones such as methyl isopyl ketone, cyclohexanone, methyl ethyl ketone, esters such as acetyl acetate and butyl acetate 1, 3-Di
  • formylizing agents include formaldehyde, formic acid, formic acid, formic acid anhydrides such as formyol (2, 2-dimethylpropionic acid), formic acid esters such as phenyl formic acid, penufluobenzaldehyde, It is possible to show oxazolyl and so on.
  • inorganic acids such as sulfuric acid
  • organic acids such as formic acid
  • polpohyde hydrides such as sodium hydroxide, sodium meta polo hydride
  • borohydrides lithium aluminum hydride and the like
  • inorganic acids such as sulfuric acid
  • organic acids such as formic acid
  • polpohyde hydrides such as sodium hydroxide, sodium meta polo hydride
  • borohydrides lithium aluminum hydride and the like
  • the reaction temperature may be appropriately selected within the range of from 100 ° C. to the reflux temperature of the solvent used, and the reaction time may be from several minutes to 96 hours, respectively. Manufacturing method 1 0
  • R c 'in general formula (51) is hydroxy A group or a single 0 -R d (R d representing J having the same meaning as above, and R c "in general formula (52) represents a chlorine atom, a bromine atom, or an iodine atom.)
  • a compound represented by the general formula (52) is reacted with a suitable halogenating agent in a suitable solvent or in the absence of a solvent to give a chlorinated compound (or an odorant compound) represented by the general formula (52) , Iodine compounds) can be produced. Suitable additives can also be used in this step.
  • the solvent may be any solvent which does not significantly inhibit the progress of the reaction, and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane, and aromatic hydrocarbons such as benzene, xylene and toluene.
  • halogenated hydrocarbons such as 1,2-dichloroethane, diethyl ether, dioxane, ethers such as tetrahydrofuran, 1,2-dimethoxyethane, dimethyl formamide, dimethyl Amides such as acetoamide, nitriles such as acetonitrile, propionitrile, acetone
  • 1,3-dimethyl-2-imidazo Lizinone, sulfolane, dimethyl Sulfoxide, alcohols such as methanol and E evening Knoll, can indicate a solvent such as water, these solvents may be used alone or as a mixture of two or more. .
  • halogenating agent for example, thionyl chloride, thionyl bromide, oxychlorochloride, oxalyl chloride, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, Rydon reagents, methanesulfonyl chloride, p-toluenesulfonyl Chloride, benzenesulfo Sulfonyl halolides such as sulfonyl chloride, sulfodinium halolides, sulfonic acid esters, chlorine, bromine, iodine, hypohalite esters, N-halogenoamines, hydrogen chloride, hydrogen bromide, sodium bromide, bromide Force lithium, cyanuric chloride, 1,3-dichloro-1,2,3-trichloroaniline, titanium (IV) chloride, vanadium chloride (IV), arsenic chloride (111), N
  • halogenating agents may be appropriately selected within the range of 0.01 to 10 times molar equivalent with respect to the compound represented by the general formula (1), or may be used as a solvent.
  • the reaction temperature may be appropriately selected within the range of from 180 ° C. to the reflux temperature of the solvent used, and the reaction time may be from several minutes to 96 hours. Manufacturing method 1 1
  • the solvent may be any solvent which does not significantly inhibit the progress of the reaction, and examples thereof include aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane, and aromatic hydrocarbons such as benzene, xylene and toluene. , Dichloromethane, black mouth Halogenated hydrocarbons such as form, carbon tetrachloride and 1, 2-dichloroetane, ethers such as diethyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxy aetane, dimethylformiamide, dimethyamide, etc.
  • aliphatic hydrocarbons such as hexane, cyclohexane and methylcyclohexane
  • aromatic hydrocarbons such as benzene, xylene and toluene.
  • Dichloromethane black mouth Halogenated hydrocarbons such as form, carbon tetrachloride
  • nitriles such as acetonitrile, propioditolyl, acetone, methyl isobutyl ketone, ketones such as cyclohexanone and methyl ethyl ketone, esters such as ethyl acetate and butyl acetate, 1,3-dimethyl-2-imidazolidino Solvents such as alcohols, sulfolanes, dimethyl sulfoxide, alcohols such as methanol and ethanol, water, etc. can be used, and these solvents can be used alone or in combination of two or more.
  • fluorinating agent it is possible to use '1, 1, 2 and 2-tetrafluorethyljetilamamine, 2-chloro-1, and 2-trifluroethyljetylamine, and trifluorinated phenylphosphorans and difluorinated products.
  • Additives may be used.
  • additives include, for example, 18-crown-16.
  • Phase transfer catalysts such as crown ethers, tetraphenylphosphonium salts, non-base salts such as calcium fluoride and calcium chloride, metal oxides such as mercury oxide, ion exchange resins, etc.
  • the above additives can also be used as a pretreatment agent for the fluorinating agent.
  • the reaction temperature may be appropriately selected from the range of 180 ° C. to the reflux temperature of the solvent used, and the reaction time may be respectively selected within the range of several minutes to 96 hours. Manufacturing method 1 2
  • the compound represented by the general formula (5 6) can be produced by following the method described in the production method 10. Manufacturing method 1 3
  • R a , R b , R c and Q ia are as defined above.
  • the compound represented by the general formula (5 8) can be produced by following the method described in Production method 11. Manufacturing method 14
  • the compound represented by the general formula (60) can be produced according to the method described in the production method 10.
  • the target substance may be isolated from the reaction system according to a conventional method, but if necessary, it is purified by performing operations such as recrystallization, column chromatography 1, and distillation. can do.
  • Tables 1 to 5 show representative compounds of the compound represented by the general formula (1) which is an active ingredient of the insecticide of the present invention, but the present invention is not limited thereto. .
  • Tables 6 to 7 show representative compounds of the compound represented by the general formula (6), but the present invention is not limited thereto.
  • Tables 8 to 10 show representative compounds of the compounds represented by the general formula (8), the general formula (11) and the general formula (13), but the present invention is not limited thereto. It is not limited.
  • n— is normal
  • Me is methyl
  • E t is ethyl
  • n—P r is normal propyl
  • i P r is isopropyl
  • N-one Bu is a normal butyl group
  • i-one Bu is an isobutyl group
  • s-Bu is a secondary butyl group
  • t-Bu is a tertiary butyl group
  • H Is a hydrogen atom
  • 0 is an oxygen atom
  • S is a sulfur atom
  • C is a carbon atom
  • N is “F” is a fluorine atom
  • C 1 is a chlorine atom
  • B r is a bromine atom
  • Ri R 2 hydrogen atom
  • GG 2 oxygen atom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
PCT/JP2004/019770 2004-01-28 2004-12-24 アミド誘導体及びその製造方法ならびにその殺虫剤としての使用方法 WO2005073165A1 (ja)

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BRPI0418471A BRPI0418471B1 (pt) 2004-01-28 2004-12-24 derivados de amida, inseticida compreendendo os mesmos e método de uso dos mesmos como inseticida
CN2004800425133A CN1926094B (zh) 2004-01-28 2004-12-24 酰胺衍生物及其制备方法和作为杀虫剂的使用方法
BR122015027139A BR122015027139B1 (pt) 2004-01-28 2004-12-24 compostos derivados de amida, inseticida compreendendo os mesmos e método de uso dos mesmos como inseticida
BR122015015718A BR122015015718B1 (pt) 2004-01-28 2004-12-24 derivados de amida
DK04808120.2T DK1714958T3 (en) 2004-01-28 2004-12-24 Amide derivatives, process for their preparation and process for their use as insecticide
NZ548793A NZ548793A (en) 2004-01-28 2004-12-24 Amide derivatives, process for preparation thereof and use thereof as insecticide
CA2554437A CA2554437C (en) 2004-01-28 2004-12-24 Amide derivatives, process for preparation thereof and use thereof as insecticide
AU2004315003A AU2004315003B2 (en) 2004-01-28 2004-12-24 Amide derivatives, process for preparation thereof and use thereof as insecticide
EP04808120.2A EP1714958B9 (en) 2004-01-28 2004-12-24 Amide derivatives, process for production of the same, and method for application thereof as insecticide
JP2005517392A JP4673748B2 (ja) 2004-01-28 2004-12-24 アミド誘導体及びその製造方法ならびにその殺虫剤としての使用方法
ES04808120.2T ES2619203T3 (es) 2004-01-28 2004-12-24 Derivados de amida, procesos para la producción de los mismos y método para su aplicación como insecticidas
US10/587,990 US8168825B2 (en) 2004-01-28 2004-12-24 Amide derivatives, process for preparation thereof and use thereof as insecticide
IL176872A IL176872A (en) 2004-01-28 2006-07-16 History of affluent and their use as insecticides
EG2006070704A EG26976A (en) 2004-01-28 2006-07-27 Amide derivatives, process for production of the same, and method for application thereof as insecticide
IL211894A IL211894A0 (en) 2004-01-28 2011-03-23 Amide derivatives
US13/427,176 US8563736B2 (en) 2004-01-28 2012-03-22 Amide derivatives, process for preparation thereof and use thereof as insecticide
US14/033,005 US8710234B2 (en) 2004-01-28 2013-09-20 Amide derivatives, process for preparation thereof and use thereof as insecticide
US14/220,673 US9185912B2 (en) 2004-01-28 2014-03-20 Amide derivatives, process for preparation thereof and use thereof as insecticide
US14/854,627 US9920026B2 (en) 2004-01-28 2015-09-15 Amide derivatives, process for preparation thereof and use thereof as insecticide
US15/871,552 US10435385B2 (en) 2004-01-28 2018-01-15 Amide derivatives, process for preparation thereof and use thereof as insecticide
US16/552,032 US10995081B2 (en) 2004-01-28 2019-08-27 Amide derivatives, process for preparation thereof and use thereof as insecticide
US17/208,474 US11760742B2 (en) 2004-01-28 2021-03-22 Amide derivatives, process for preparation thereof and use thereof as insecticide
US18/229,277 US20230373947A1 (en) 2004-01-28 2023-08-02 Amide derivatives, process for preparation thereof and use thereof as insecticide

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