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WO1996015093A1 - Composes dihalopropene, leur utilisation et intermediaires utilises pour leur production - Google Patents

Composes dihalopropene, leur utilisation et intermediaires utilises pour leur production Download PDF

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WO1996015093A1
WO1996015093A1 PCT/JP1995/002320 JP9502320W WO9615093A1 WO 1996015093 A1 WO1996015093 A1 WO 1996015093A1 JP 9502320 W JP9502320 W JP 9502320W WO 9615093 A1 WO9615093 A1 WO 9615093A1
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PCT/JP1995/002320
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Japanese (ja)
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Masaya Suzuki
Noriyasu Sakamoto
Toshio Nagatomi
Kimitoshi Umeda
Kazunori Tsushima
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Sumitomo Chemical Company, Limited
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Priority to AU38567/95A priority Critical patent/AU3856795A/en
Publication of WO1996015093A1 publication Critical patent/WO1996015093A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/17—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/21—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with the sulfur atom of the thio group bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Definitions

  • the present invention relates to a dihalobopen pen compound, its use, and an intermediate for its production.
  • the present invention provides a compound represented by the general formula (1):
  • R 1 -ZY-OCH 2 CH CX 2
  • R 1 is an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a haloalkenyl group having 2 to 6 carbon atoms, and 3 to 9 carbon atoms.
  • T represents a cycloalkenylalkyl group having 6 to 8 carbon atoms which may be substituted with an alkyl group, or
  • A represents an optionally substituted fuunyl group, an optionally substituted naphthyl group or an optionally substituted heterocyclic group
  • R 2 , R 3 , RR 5 and R 6 each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms or a trifluoromethyl group,
  • R 7 and R 8 each independently represent a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, a trifluoromethyl group or a halogen atom,
  • R 9 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms,
  • R 1 () represents a hydrogen atom, a halogen atom or a methyl group, i represents an integer from 0 to 6, j represents an integer from 1 to 6, k represents an integer from 0 to 4, 1 (el ) Represents 1 or 2, and m represents an integer from 0 to 2.
  • Z represents an oxygen atom, a sulfur 'atom or an NR 12 group (where R 12 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms).
  • R 13 is each independently a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkyl group having 2 to 4 carbon atoms or a group having 2 to 4 carbon atoms.
  • R 13 represents 4 Haroaruke two Le group, p is in. ⁇ ! ⁇ 9 each structural formula which represents the integer from 0 to 3, the binding of the left one of the two bonds are assumed to be bonded to ⁇ . represented by) ⁇ !, ⁇ 2, ⁇ 3 , ⁇ 4, ⁇ 5,
  • Ye Upsilon 7, represents a Upsilon 8 or Upsilon 9.
  • X each independently represents a chlorine atom or a bromine atom.
  • halopropene compound hereinafter, referred to as the compound of the present invention
  • insecticide and acaricide containing the compound as an effective component
  • the present invention further provides a compound of the general formula (2) useful as an intermediate for producing some of the compounds of the present invention:
  • A represents, as an embodiment of A, a phenyl group which may be substituted with (R 14 ) q or a naphthyl group which may be substituted with (R 14 ), or an oxygen atom, a zeo atom or comprising at least 1 pc a ⁇ atoms, including at least 1 Ke and (R 1 4) or represents an optionally substituted 6-membered heterocyclic ring group q, or an oxygen atom, I O ⁇ atom or a nitrogen atom, (R 14 ).
  • R 14 is a halogen atom, a cyano group, a nitro group, an (alkoxy having 1 to 4 carbon atoms) carbonyl group, an alkyl group having 1 to 8 carbon atoms, Haloalkyl group having 1 to 3 carbon atoms, alkoxy group having 1 to 7 carbon atoms, haloalkoxy group having 1 to 3 carbon atoms, alkylthio group having 1 to 3 carbon atoms, haloalkylthio group having 1 to 3 carbon atoms, 1 to 2 carbon atoms Alkylsulfinyl group having 1 to 2 carbon atoms, haloalkylsulfinyl group having 1 to 2 carbon atoms, haloalkylsulfonyl group having 1 to 2 carbon atoms, alkenyloxy group having 3 to 6 carbon atoms, carbon number 3 From 6 to 6 haloalkenyloxy groups, alkenyl with 2 to
  • Q when Q is 2 to 5, two adjacent R 14 are bonded to each other at the terminal to represent a trimethylene group, a tetramethylene group, a methylenedioxy group or an ethylenedioxy group. ].
  • the alkyl group having 1 to 10 carbon atoms represented by R 1 includes, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group.
  • haloalkyl group having 1 to 5 carbon atoms represented by R 1 includes, for example, a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group,
  • 3,3-trifluoropropyl group 1,1fluoropropyl group, 2-chloropropyl group, 3-bromopropyl group, 1,1,2,2,2-pentafluorofluoroethyl group, 2-odoethyl group, 2 1,2-Dichloromethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoro Loethyl group, 2-bromo-1,2.2-trifluoroethyl group, 2,2,2-trichloroethyl group, 2,2,
  • the alkenyl group having 2 to 10 carbon atoms represented by R 1 includes, for example, a vinyl group, an aryl group, an isopropyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 2-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 1-ethyl-2-propenyl group, 2- Ethyl-2-propenyl group, 1-methyl-3-butenyl group, 2-methyl-3-butenyl group, 3-methyl-3-butenyl group, 2-hexenyl group, 3-hexenyl group, 4-1 Xenyl, 5-hexenyl, 2-methyl-2-pentenyl, 1,3-dimethyl-2-butenyl, 1-methyl-4-pentenyl, 1-ethyl-2-butenyl, 2-ethyl
  • the haloalkenyl group having 2 to 6 carbon atoms represented by R 1 includes, for example, 2,2-dichloroethenyl group, 2,2-dibromoethenyl group, 3,3-dichloro-1--2-propenyl group, 3.3-dibromo-12-propenyl group, 2,3-dichloro-12-probenyl group, 2,3-dibut-2-amine 2-propenyl group, 2-chloro-2-propenyl group , 3-chloro-2-propenyl group, 2-bromo-
  • the alkynyl group having 3 to 9 carbon atoms represented by R 1 includes, for example, 2-propynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-pentynyl group Group, 3-pentynyl group, 4-pentynyl group, 1-methyl-3-butynyl group, 2-methyl-3-butynyl group, 1-ethyl-2-propynyl group, 2-hexynyl group, 3-hexynyl group , 2-heptinyl group, 3-butynyl group, 1-ethynylhexyl group, 3-noninyl group, 5-hexynyl group, etc.
  • the haloalkynyl group having 3 to 5 carbon atoms represented by R 1 is, for example, 3 —cyclo—2-propynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 1-methyl-3 —Chloro-2-propynyl group, 1-methyl-3-promo-2-propynyl group, 1-methyl-13-ododo-2-propynyl group, 4-chloro-2-butynyl group, 4-chloro-3-butynyl group, 4— Bromo-3-butynyl, 5-chloro- 4-pentynyl, 5-bromo- 4-pentynyl, 4-chloro-2-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 4-chloro-1-methyl One 3-butynyl group, 4-bromo-1-methyl-3-butynyl group, 3-chloro-
  • the alkoxyalkyl group having 2 to 7 carbon atoms represented by R 1 includes, for example, a methoxymethyl group, an ethoxyquinmethyl group, a propyloxymethyl group, an isopropylpyroxymethyl group, a 2-methoxethyl group, a 1-methoxyl group,
  • 2-ethoxyquinethyl group 1-ethoxyquinethyl group, 3-methoxypropyl group, 2-methoxypropyl group, 1-methoxypropyl group, 2-methoxyethoxy Methylethyl group, 2-propyloxyethyl group, 2-isopropyloxyethyl group, 2-ethoxy-2-methylethyl group, 2-ethoxy-1-methylethyl group, 2-methoxybutyl group, 1-ethyl-2-methyloxyethyl group, 3-ethoxypropyl group, 3-methoxybutyl group, 3-methoxy-2-methylpropyl group, 3-methoxy-1-methylpropyl group, 2-butoxyethyl group, 3-methoxy-3-methylbutyl group, 2-butoxy 1 is a monomethylethyl group, etc.
  • alkylthioalkyl group having 2 to 7 carbon atoms represented by R 1 examples include a methylthiomethyl group, an ethylthiomethyl group, a propylthiomethyl group, an isopropylthiomethyl group, a 2-methylthioethyl group, a 1-methylthioethyl group, 2-ethylthioethyl group, 1-ethylthioethyl group, 3-methylthiopropyl group, 2-methylthiopropyl group, 1-methylthiopropyl group, 2-methylthio-1-methylethyl group, 2-propylthioethyl group, 2 — Isopropylthioethyl group, 2-ethylthiopropyl group, 2-ethylthio-11-methylethyl group, 2-methylthiobutyl group, 1-ethyl-2-methylthioethyl group, 3-ethylthiopropyl group, 3-methylthiobut
  • an alkyl group having 1 to 4 carbon atoms an alkoxy group having 1 to 3 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms which may be substituted by a haloalkoxy group having 1 to 3 carbon atoms represented by R 1
  • an alkyl group having 1 to 4 carbon atoms means a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, Butyl, sec-butyl or tert-butyl,
  • the alkoxy group having 1 to 3 carbon atoms is a methoxy group, an ethoxy group, a propoxy group or an isopropoxy group
  • R 1 represents an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms which may be substituted with a haloalkoxy group having 1 to 3 carbon atoms.
  • the haloalkoxy group having 1 to 3 carbon atoms is, for example, a trifluoromethoxine group, a difluoromethoxy group, a bromodifluoromethoxy group, a 2,2.2-trifluorofluorethoxy group, a 2,2,2,1 1-pentafluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-chloro-1,1,2, -trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy A 1,1,2,2-tetrafluoroethoxy group, a 3,3,3,2.2,1-hexafluoropropoquine group, and the like;
  • alkyl group having 1 to 4 carbon atoms an alkoxy group having 1 to 3 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms which may be substituted by a haloalkoxy group having 1 to 3 carbon atoms represented by R 1
  • the cycloalkyl group having 3 to 6 carbon atoms is a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group,
  • the alkyl group having 1 to 4 carbon atoms means a methyl group, an ethyl group, Propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl;
  • the cycloalkylalkyl group having 4 to 9 carbon atoms in the cycloalkylalkyl group having 4 to 9 carbon atoms L which may be substituted with an alkyl group having 1 to 4 carbon atoms represented by R 1 is, for example, cycloalkyl Propylmethyl group, 1-cyclopropylpropyl group, 2-cyclopropylethyl group, cyclobutylmethyl group, cyclopentylmethyl group, 2-cyclopentylethyl group, 3-cyclopentylpropyl group, cyclohexy
  • R 1 may also be substituted with one carbon atoms represented by R 1 in 4 alkyl t, in cycloalkenyl group having 5 to 6 carbon atoms, the alkyl group having 1 to 4 carbon atoms, a methyl group, Echiru group, Propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl;
  • the cycloalkenyl group having 5 to 6 carbon atoms in the cycloalkenyl group having 5 to 6 carbon atoms which may be substituted with the alkyl group having 1 to 4 carbon atoms represented by R 1 is a 1-cyclopentenyl group, 2 —Cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, or 3-cyclohexenyl;
  • cycloalk 'Keniruarukiru group having carbon atoms 6 be substituted with an alkyl group having from 1 to 4 carbon atoms represented by R 1 8, the Al kill group having 1 to 4 carbon atoms, a methyl group, Echiru group, Propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl;
  • the cycloalkenylalkyl group having 6 to 8 carbon atoms in the cycloalkenylalkyl group having 6 to 8 carbon atoms which may be substituted by the alkyl group having 1 to 4 carbon atoms represented by R 1 is, for example, 1- Cyclopentenylmethyl group,
  • the halogen atom represented by R 7 , R 8 , R 9 , R 10 , R 13 and R 14 is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom,
  • the alkyl group having a carbon purple number of 1 to 4 represented by R 9 and R 13 is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group or a tert-butyl group.
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R 14 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, Isopentyl group, neopentyl group, tert-pentyl group, hexyl group, heptyl group, 1,1-dimethylhexyl group, 1-methylbutyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, isohexyl group , A 1-methylpentyl group, a 2-ethylbutyl group, an octyl group, a 1-methylhexylbutyl group, etc.
  • the haloalkyl group having 1 to 3 carbon atoms represented by R 9 , R 13 and R 14 includes, for example, trifluoromethyl group, trichloromethyl group, difluoromethyl group, bromodifluoromethyl group, 2,2,2 2-trifluoroethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 1-fluoroethyl group, 1-chloroethyl group, 1-bromoethyl group, 3, 3, 3, 2 1,2-pentafluoropropyl group, 3,3,3-trifluoropropyl group, 11-fluoropropyl pill group, 2-chlorobu pill group, 3-bromopropyl group, etc.
  • the alkoxy group having 1 to 3 carbon atoms represented by R 9 is a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group,
  • the haloalkoxy group having 1 to 3 carbon atoms represented by R 9 and R 14 is, for example, a trifluoromethoxy group, a difluoromethoxy group, a bromodifluo group.
  • the alkyl group having 1 to 3 carbon atoms represented by R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 and R 15 is a methyl group, an ethyl group, Propyl or isopropyl;
  • the alkoxy group having 1 to 7 carbon atoms represented by R 14 is, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, an isobutoxy group, a tert-butoxy group, Pentyloxy, isopentyloxy, 1-methylbutyne, 1-ethylpropoxy, neopentyloxy, tert-pentyloxy, 1,2-dimethylpropoxy, hexyloxy, heptyloxy, etc. ,
  • the alkylthio group having 1 to 3 carbon atoms represented by R 14 is a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group,
  • the haloalkylthio group having 1 to 3 carbon atoms represented by R 14 includes, for example, trifluoromethylthio group, difluoromethylthio group, bromodifluoromethylthio group, 2.2,2-trifluoroethylthio group, 2-chloro- 1,1,2-Trifluoroethylthio group, 2-Bromo-1,1.2-Trifluoroethylthio group, 1,1,2.2-Tetrafluoroethylthio group, 2-chloro Roethylthio, 2-fluoroethylthio, 2-bromoethylthio, 1,1,2,2,2-pentafluoroethylthio, 3-fluoropropylthio, 3-chloropropyl Thio group, 3-bromopropylthio group, 3,3.3,2,2-pentafluoropropylthio group, 3,3,3-trifluoropropylthio group, etc.
  • the alkenyloxy group having 3 to 6 carbon atoms represented by R 14 includes, for example, an aryloxy group, a 2-methyl-2-propenyloxy group, a 1-methyl-2-propenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, A methyl-2-butenyloxy group, a 2-methyl-2-butenyloxy group, a 2-pentenyloxy group, a 2-hexenyloxy group, etc.
  • Examples of the haloalkenyloxy group having 3 to 6 carbon atoms represented by R 14 include, for example, 3,3-dichloro-2-propenyloxy group, 3,3-dibutene 2-phenylpropoxy group, 2.3 —Dichloro-2-propenyloxy group, 2,3-diphenyl 2-, propenyloxy group, 2-chloro-2-propenyloxy group, 3-chloro-2-propenyloxy group, 2-bromo-2-pro Phenyloxy group, 3-fluoro-3-chloro-2-propenyloxy group, 3-methyl-4,4,4-trifluoro-2-butenyloxy group, 3-chloro-2-butenyloxy group, etc.
  • the alkenyl group having 2 to 4 carbon atoms represented by R 13 and R 14 is, for example, a vinyl group, an isopropyl group, a 1-propyl group, a 2-methyl-11-propyl group, a 1-methyl group.
  • the haloalkenyl group having 2 to 4 carbon atoms represented by R 13 and R 14 is, for example, 2,2-dichloroethenyl group, 2,2-dibromoethenyl group, 3,3
  • the alkynyl group having 2 to 4 carbon atoms represented by R 14 is, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group,
  • the haloalkynyl group having 2 to 4 carbon atoms represented by R 14 includes, for example, a chloroethynyl group, a bromoethynyl group, an odoethynyl group, a 3-chloro-2-propynyl group, a 3-promo-2-propynyl group, and a 3-propynyl group.
  • the alkoxyalkyl group having 2 to 4 carbon atoms represented by R 14 includes, for example, methoxymethyl group, ethoxymethyl group, propyloxymethyl group, isopropyl pyroxymethyl group, 2-methoxethyl group, and 1-methyl group.
  • the alkylthioalkyl group having 2 to 4 carbon atoms represented by R 14 includes, for example, methylthiomethyl group, ethylthiomethyl group, propylthiomethyl group, isopropylthiomethyl group, 2-methylthioethyl group, 1-methylthioethyl group Group, 2-ethylthioethyl group, 1-ethylthioethyl group, 3-methylthiopropyl group, 2-methylthiopropyl group, 1-methylthiopropyl group, 2-methylthio-1-methylethyl group, etc.
  • the cycloalkyl group having 3 to 6 carbon atoms represented by R 14 is, for example, Chloropropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.
  • the cycloalkenyl group having a carbon violet number of 5 to 6 represented by R 14 is, for example, 1-cyclopentenyl group, 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclopentyl group, Hexenyl group, 3-cyclohexenyl group, etc.
  • the cycloalkyloxy group having 3 to 6 carbon atoms represented by R 14 is, for example, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc.
  • Examples of the cycloalkenyloxy group having 5 to 6 carbon atoms represented by R 14 include a 1-cyclopentenyloxy group, a 2-cyclopentenyloxy group, a 3-cyclopentenyloxy group, and a 1-cyclopentyloxy group. Hexenyloxy, 2-cyclohexenyloxy, 3-cyclohexenyloxy, etc.
  • the alkylsulfinyl group having 1 to 2 carbon atoms represented by R 14 is a methylsulfinyl group or an ethylsulfinyl group,
  • the alkylsulfonyl group having 1 to 2 carbon atoms represented by R 14 is a methylsulfonyl group or an ethylsulfonyl group,
  • the haloalkylsulfinyl group having 1 to 2 carbon atoms represented by R 14 includes, for example, trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, perfluoroethylsulfinyl group, and the like.
  • Examples of the haloalkylsulfonyl group having 1 to 2 carbon atoms represented by R 14 include a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a perfluoroethylsulfonyl group, and the like.
  • the (amino having 1 to 2 carbon atoms) aminocarbonyl group represented by R 14 is a methylaminocarbonyl group or an ethylaminocarbonyl group
  • the [di (alkynole) amino] carbon atom represented by R 14 is a dimethylaminocarbonyl group, an N-methyl-N-ethylaminocarbonyl group, a acetylaminocarbonyl group, or the like,
  • R represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a haloalkoxy group having 1 to 3 carbon atoms, respectively.
  • An alkyl group having 1 to 4 carbon atoms in a phenyl group, a phenoxy group, a benzyl group or a benzyloxy group which may be substituted with: a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group , Tert-butyl or isobutyl,
  • a haloalkyl group having 1 to 3 carbon atoms in a phenyl group, a phenoxy group, a benzyl group or a benzyloxy group which may be substituted with a group is, for example, a trifluoromethyl group, a difluoromethyl group, a bromodifluoromethyl group , 2,2—difluoroethyl group, 2,
  • the heterocyclic ring in the heterocyclic group which may be substituted represented by A is, for example, isooxazole, isothiazole, thiazole, 1,3,4-thiadiazole, pyrrole, furan, thiophene, pyrazole, imidazole, 2,3-triazole, 1,2,4-triazole, 1.2,3,4-tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, 1,2.4-triazine, 1,3,5-triazine, Indole, benzofuran, thianaphthalene, indazole, benzimidazole, benzotriazole, benzisoxazole, benzoxazole, benzothiazole, quinoline, isoquinoline, quinoxaline, quinazole, pyridin, pyrazine, tetrahydrofuran , Tetrahydrobiran, virazoline and the like.
  • R 1 is Q, and A is (R 14 ).
  • R 1 is Q 2
  • A is (R 14) which may be substituted with Fuyuniru group, (optionally substituted with R 2-pyridyl group or (R 14), in but it may also be substituted Compounds that are 3-pyridyl groups;
  • R 1 is Q 3 , and an A group, a phenyl group optionally substituted with (R) q , a 2-pyridyl group optionally substituted with (R ′′) or (R 14 ) A compound that is a 3-pyridyl group;
  • R 1 is Q 4 , Q 5 , Q 6 , Q 7 , Q 8 or Q 9 , and is a phenyl group optionally substituted with (R 14 ); substituted with (R 14 ) q A compound which is a 2-pyridyl group or a 3-pyridyl group optionally substituted with (R 14 ) q ;
  • Preferred embodiments of Z include an acid atom
  • Y Preferred embodiments of Y include Y,
  • a preferred embodiment of (R 13 ) p is a compound wherein R 13 is a halogen atom, and p is 0 or 1.
  • oxygen atom In a preferred embodiment of B, oxygen atom, C0 2 group or CONH group.
  • Y is Y, R 1 is Q, and A is a phenyl group or (R 14 ) optionally substituted with (R 14 ) Q.
  • Y is Y
  • R 1 is Q 2
  • A is (R 14 ) Q
  • Z is an oxygen atom
  • R 2 , R 3 and R 4 are A compound which is a hydrogen atom, i is an integer of 0 to 3, R 13 is a halogen atom, and p is 0 or 1;
  • R 1 is Q 3
  • A is substituted with (R 14) may be substituted by Q Hue group, in which may be substituted 2-pyridyl group, or (R ") q
  • Q is an oxygen atom
  • B is an oxygen atom
  • i is 2 or 3
  • R 13 is a halogen atom
  • compound p is 0 or 1 and the like.
  • the compound of the present invention can be produced, for example, by the following methods (Production method A) to (Production method I).
  • R 1 is other than C
  • Z is an oxygen atom
  • Y is Y ,, ⁇ 2 , ⁇ 3 or ⁇ 4 , that is, ⁇ is 10
  • R 1 has the same meaning as described above.
  • the above reaction is preferably carried out in the presence of a suitable dehydrating agent, if necessary, in an inert solvent.
  • a suitable dehydrating agent examples include dicyclohexyl carbodiimidodialkyl (eg, d—C 4 ) azodicarboxylate (diethyl azodicarboxylate, diisopropyl azodicarboxylate). Rate Etc.)
  • Trialkyl eg, d—C 2 c
  • phosphine or triarylphosphine triphenylphosphine, trioctylphosphine, tributylphosphine, etc.
  • solvent used examples include hydrocarbons such as benzene, xylene, and toluene; ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; and carbon tetrachloride, dichloromethane, and benzene.
  • hydrocarbons such as benzene, xylene, and toluene
  • ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane
  • carbon tetrachloride dichloromethane
  • benzene halogenated hydrocarbons such as dichlorobenzene can be mentioned.
  • the reaction temperature can range from 20 ° C to 200 ° C or the boiling point of the solvent used in the reaction.
  • the molar ratio of the raw materials and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution can be subjected to ordinary post-treatments such as extraction with an organic solvent, kanshu, etc. to isolate the target compound of the present invention. If necessary, it can be further purified by conventional procedures such as chromatography, distillation, recrystallization, etc.
  • R 1 has the same meaning as described above, and L 1 represents a halogen atom (a chlorine atom, a bromine atom, an iodine atom, etc.), a mesyloxy group or a tosyloxy group.
  • L 1 represents a halogen atom (a chlorine atom, a bromine atom, an iodine atom, etc.), a mesyloxy group or a tosyloxy group.
  • a suitable base such as acetone and key Sanon methyl E chill ketone, cyclohexane, 1.
  • Examples of the base used include lithium hydroxide, sodium hydroxide, potassium hydroxide, hydroxide of alkali metal or alkaline earth metal such as calcium hydroxide, lithium carbonate, lithium carbonate, sodium carbonate, Alkali metal or alkaline earth metal such as calcium carbonate, alkaline hydride, lithium hydride, sodium hydride, alkaline hydride, calcium hydride, etc.Alkali metal or alkaline earth metal hydride, sodium main Tokishido, sodium Muetokindo, Al force Li metal alkoxides such as Riumu tert- butoxide (e.g., C! one C 4), Bok Riechiruamin, organic bases such like et be such as pyridine.
  • alkali metal or alkaline earth metal such as calcium hydroxide, lithium carbonate, lithium carbonate, sodium carbonate, Alkali metal or alkaline earth metal such as calcium carbonate, alkaline hydride, lithium hydride, sodium hydride, alkaline
  • a catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mol based on 1 mol of the compound represented by the above general formula (6). You may add in proportion.
  • an ammonium salt eg, triethylbenzylammonium chloride
  • the reaction temperature can usually range from 150 ° C. to the boiling point of the solvent used in the reaction or 150 ° C., but from 150 ° C. to the boiling point of the solvent used in the reaction or 100 ° C. Temperatures up to ° C are more desirable.
  • the molar ratio of the starting material and the base to be used for the reaction can be arbitrarily set, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation and recrystallization.
  • the above reaction is preferably performed in an inert solvent in the presence of a suitable base.
  • Solvents used include ketones such as acetone, methyl ethyl ketone and cyclohexanone, 1,2-dimethoxetane, tetrahydrofuran, dioxane, and dialkyl (eg, C, 1 C 4 ) ether (eg, , NN-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid triamide, sulfolane, acetonitrile, nitromethane, etc., polar solvents such as dichloromethane, chloroform, 1,2-dichloroethane And halogenated hydrocarbons such as benzene, and hydrocarbons such as toluene, benzene and xylene, and water. If necessary, use a mixture of these solvents be able to.
  • Examples of the base to be used include lithium hydroxide, sodium hydroxide, potassium hydroxide, calcium hydroxide and other alkali metal or alkaline earth metal hydroxides, lithium carbonate, potassium carbonate, sodium carbonate, and the like.
  • Alkali metal or alkaline earth metal hydrides such as alkali metal or alkaline earth metal carbonates such as calcium carbonate, lithium hydride, sodium hydride, potassium hydride, calcium hydride, etc.
  • Metal alkoxides such as sodium methoxide, sodium methoxide, potassium te-butoxide
  • a catalyst such as an ammonium salt (eg, triethylbenzene ammonium chloride) may be added to the reaction system in an amount of 0.1 to 1 mol per mol of the phenol compound represented by the general formula (7). May be added.
  • the reaction temperature is usually from 120 ° C to the boiling point of the solvent used in the reaction or a force capable of taking a range from 150 ° C to 150 ° C to the boiling point of the catalyst used in the reaction or 100 ° C. Temperatures up to C are more desirable.
  • the molar ratio of the starting material and the base to be used for the reaction can be arbitrarily set, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution After completion of the reaction, the reaction solution can be subjected to ordinary post-treatments such as extraction with an organic solvent, ozone, and the like to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation and recrystallization.
  • the above reaction can be carried out in an inert solvent in the presence of zinc metal, if necessary.
  • inert solvent examples include hydrocarbons such as benzene, xylene and toluene, ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran and dioxane, dichloromethane, 1,2-dichloroethane, and chloroform. And halogenated hydrocarbons such as benzene (excluding carbon tetrabromide and carbon tetrachloride).
  • the reaction temperature can range from 130 to the boiling point of the solvent used in the reaction or 150 ° C.
  • Trialkyl (e.g., 1 C 2 D ) phosphine or triaryl phosphine to be subjected to the reaction includes, for example, triphenylphosphine-trioctylphosphine, and metal zinc used as necessary is dust. Is preferred.
  • the molar ratio of the raw materials and reagents to be used for the reaction can be set arbitrarily, but 1 to 5 moles of carbon tetrabromide (tetrachloride) is used per mole of the aldehyde compound of the general formula (9).
  • the ratio of the kill phosphine or the triaryl phosphine is 2 to 10 mol.
  • the ratio of the zinc is preferably 1 to 5 mol, or the reaction is advantageously carried out at a ratio close thereto.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, purification can be carried out by ordinary procedures such as chromatography, distillation, and recrystallization.
  • dehydrating agent for example, hexyl Cal positive imide dicyclohexyl, dialkyl (e.g., d-c 4) ⁇ zone dicarboxylate rate Bok (Jechiruazo dicarboxylate, diisopropyl ⁇ zone dicarboxylate, etc.) Single trialkyl (Eg, C, 1 c 2 () ) phosphine or triaryl phosphine (triphenyl phosphine, trioctyl phosphine, tributyl phosphine, etc.), and the like.
  • solvent used examples include hydrocarbons such as benzene, kylene and toluene, ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran and dioxane or carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.
  • hydrocarbons such as benzene, kylene and toluene
  • ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran and dioxane or carbon tetrachloride
  • dichloromethane chlorobenzene
  • dichlorobenzene halogenated hydrocarbons
  • the reaction temperature can range from 20 ° C to 200 ° C or the boiling point of the solvent used in the reaction.
  • the molar ratio of the raw materials and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution can be subjected to ordinary post-treatments such as extraction with an organic solvent, concentration, and the like to isolate the target compound of the present invention. If necessary, chromatograph The product can be further purified by filtration, distillation, recrystallization and other operations.
  • Y I (), BR 2 , R 3, R 4, i and X are as defined above c
  • the above reaction is carried out in the presence of a suitable base, preferably carried out in an inert solvent c
  • the solvent used include ketones such as acetone, methyl ethyl ketone and cyclohexanone, 1,2-dimethoxetane, tetrahydrofuran, dioxane, dialkyl (eg, d—C 4 ) ether (Eg, methyl ether, diisopropyl ether, etc.), polar solvents such as N.N-dimethylformamide, dimethyl sulfoxide, hexamethylphosphoric acid triamide, sulfolane, acetonitrile, nitromethane, dichloromethane, Examples thereof include halogenated hydrocarbons such as chloroform, 1,2-dichloroethane, and benzene, hydrocarbons such as toluene, benzene, and xylene, and water. If necessary, a mixed solvent of these solvents can
  • Examples of the base used include hydroxides of alkali metals or alkaline earth metals such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, lithium carbonate, potassium carbonate, sodium carbonate, and the like.
  • Alkali metal or alkaline earth metal carbonates such as calcium carbonate, alkali metal or alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride, calcium hydride, etc.
  • Alkyli metal alkoxides such as toxide, sodium methoxide and potassium tert-butoxide (eg, organic bases such as d-CJ, triethylamine, pyridine and the like.
  • a catalyst such as ammonium salt eg, triethylbenzylammonium chloride
  • the reaction may be carried out in an amount of 0.01 to 1 mol per 1 mol of the compound represented by the formula (11)
  • the reaction temperature is usually from 120 ° C. to the boiling point of the solvent used in the reaction, or from 1 ° C.
  • a force that can be in the range of 500 ° C ⁇ — a temperature from 5 ° C to the boiling point of the solvent used in the reaction or 100 ° C is more desirable.
  • the molar ratio of the starting material and the base to be used for the reaction can be set arbitrarily. 95/02320
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation and recrystallization.
  • the above reaction is preferably carried out in the presence of a suitable dehydrating agent, if necessary, in an inert solvent.
  • dehydrating agent for example, hexyl Cal positive imide dicyclohexyl, dialkyl (eg, C, one c 4) ⁇ zone dicarboxylate (Jechiruazoji Karubokishire Bok, diisopropyl ⁇ zone dicarboxylate Kin rate, etc.)
  • dialkyl eg, C, one c 4
  • zone dicarboxylate Jechiruazoji Karubokishire Bok, diisopropyl ⁇ zone dicarboxylate Kin rate, etc.
  • Single thoria alkyl Eg, C! —C 20
  • phosphine or triarylphosphine such as triphenylphosphine, trioctylphosphine, and tributylphosphine.
  • solvent used examples include hydrocarbons such as benzene, xylene, and toluene, ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, and dioxane, and carbon tetrachloride, dichloromethane, cyclobenzene, and dichlorobenzene.
  • hydrocarbons such as benzene, xylene, and toluene
  • ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, and dioxane
  • carbon tetrachloride dichloromethane
  • cyclobenzene cyclobenzene
  • dichlorobenzene halogenated hydrocarbons
  • the reaction temperature can range from 20 ° C to 200 ° C or the boiling point of the solvent used in the reaction.
  • the molar ratio of the raw materials and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation and recrystallization.
  • the above reaction is preferably performed in an inert solvent in the presence of a suitable base.
  • the solvent to be used include acetone, methyl E chill ketone and key Sanon cyclohexane, 1. 2-dimethyl Bok Kishetan, as tetrahydrofuran, Jiokisan, dialkyl (eg, C!
  • One C 4) ether e.g., Ethers such as dimethyl ether, diisopropyl ether, etc.
  • polar solvents such as N, N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid triamide, sulfolane, acetonitrile, nitromethane, dichloromethane, chloroform, 1
  • halogenated hydrocarbons such as 1,2-dichloroethane and benzene
  • hydrocarbons such as toluene, benzene and xylene, and water. If necessary, a mixed solvent of these solvents can be used.
  • Examples of the base used include hydroxides of alkali metal or alkaline earth metal such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, lithium carbonate, potassium carbonate, sodium carbonate, and carbonic acid.
  • Alkali metal or alkaline earth metal hydride such as alkali metal or alkaline earth metal carbonate such as calcium, lithium hydride, sodium hydride, potassium hydride, calcium hydride, etc.
  • sodium main Tokishido, sodium Muetokishido Al force Li gold ⁇ alkoxides such force Riumu tert- butoxide (e.g., C -! C 4), Bok Riechiruami down, and organic bases such as pyridine Ru mentioned.
  • a catalyst such as an ammonium salt (eg, triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mol of the compound represented by the general formula (16). ⁇ 1 mole ratio may be added.
  • an ammonium salt eg, triethylbenzylammonium chloride
  • the reaction temperature is usually from 120 ° C to the boiling point of the solvent used in the reaction or from 150 ° C to the boiling point of the solvent used in the reaction. Temperatures up to C are desirable. / P95 / 02320
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation and recrystallization.
  • R 1 Q 3 or C and 5 and Y is Y !, ⁇ 2 , ⁇ 3 or ⁇ 4 , ie ⁇ ⁇ is ⁇ 1 () )
  • reaction is preferably carried out in the presence of a suitable dehydrating agent, if necessary, in an inert solvent.
  • Examples of the dehydrating agent to be used include dicyclohexyl carbodiimide, dialkyl (eg, C i -C 4 ) azodicarboxylate (eg, getyl azodicarboxylate, diisopropyl azodicarboxylate), and trialkyl.
  • dialkyl eg, C i -C 4
  • azodicarboxylate eg, getyl azodicarboxylate, diisopropyl azodicarboxylate
  • trialkyl Eg, C 1 -C 2 ()
  • phosphine or triaryl phosphine triphenyl phosphine, trioctyl phosphine, tributyl phosphine, etc.
  • solvent used examples include hydrocarbons such as benzene, kylene and toluene, ethers such as dimethyl ether, diisopropyl ether, tetrahydrofuran and dioxane or carbon tetrachloride, dichloromethane, cyclobenzene, and dichlorobenzene. And other halogenated hydrocarbons.
  • the reaction temperature can range from 120 ° C. to 200 ° C. or the boiling point of the solvent used in the reaction.
  • the molar ratio of the raw materials and the dehydrating agent to be used for the reaction can be set arbitrarily, but it is advantageous to carry out the reaction in an equimolar or close ratio.
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to isolate the target compound of the present invention. If necessary, it can be further purified by usual procedures such as chromatography, distillation, and repacking.
  • the compounds of the present invention include biologically active optically active isomers ((+)-isomer, (-) integral) and mixtures thereof in all ratios.
  • biologically active optically active isomers ((+)-isomer, (-) integral) and mixtures thereof in all ratios.
  • the compound of the present invention also includes each geometric isomer having biological activity (cis isomer, trans isomer), and a mixture thereof in any ratio.
  • CC 1 2 CHCH 2 CH 2
  • CH 3 (CH 2) 4 CH CHCH 2 CH 2 CH ⁇ CCH 2
  • CC 1 2 CH 2 CH 3 C ⁇ CCH 2 CH 2
  • CHB r CHCH 2 CH ⁇ CCH 2 CH (CH 3 )
  • CH 2 CC 1 CH 2 CH ⁇ CCH (CH 3 ) CH 2
  • CC 1 2 CHCH 2 CH 3 CH 2 C ⁇ CCH 2 CH 2
  • CH 3 CC 1 CHCH 2 CH 3 (CH 2 ), C ⁇ CCH 2 CH 2
  • CH 2 C 1 CH CHCH 2 CH ⁇ C (CH 2 ) 3 CH 2

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Abstract

L'invention concerne un composé dihalopropène représenté par la formule générale (I) et présentant d'excellentes propriétés insecticides et miticides. Dans cette formule (I) R1 représente alkyle C¿1?-C10 etc.; Z représente oxygène etc.; Y représente un reste naphtalène auquel Z et O sont liés respectivement en position 1- et 5-; et X représente chloro etc.
PCT/JP1995/002320 1994-11-14 1995-11-14 Composes dihalopropene, leur utilisation et intermediaires utilises pour leur production WO1996015093A1 (fr)

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AU38567/95A AU3856795A (en) 1994-11-14 1995-11-14 Dihalopropene compounds, use thereof, and intermediates for production thereof

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JP27953394 1994-11-14
JP6/279533 1994-11-14
JP7/258986 1995-10-05
JP25898695 1995-10-05

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869506A (en) * 1996-01-31 1999-02-09 Sumitomo Chemical Company, Limited Fluoropropene compound, an insecticide containing the same and an intermediate for production thereof
WO2005095330A1 (fr) * 2004-03-31 2005-10-13 Bayer Cropscience Ag Nouveaux derives de dichloropropene
US7192965B2 (en) 2002-06-28 2007-03-20 Syngenta Crop Protection, Inc. 4-(3,3-dihalo-allyloxy)phenoxy alkyl derivatives

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Publication number Priority date Publication date Assignee Title
JPS4886835A (fr) * 1972-02-04 1973-11-15
JPS491526A (fr) * 1972-03-16 1974-01-08
JPH07188088A (ja) * 1993-10-19 1995-07-25 Sumitomo Chem Co Ltd ジハロプロペン化合物、それを有効成分とする殺虫、殺ダニ剤およびその製造中間体

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4886835A (fr) * 1972-02-04 1973-11-15
JPS491526A (fr) * 1972-03-16 1974-01-08
JPH07188088A (ja) * 1993-10-19 1995-07-25 Sumitomo Chem Co Ltd ジハロプロペン化合物、それを有効成分とする殺虫、殺ダニ剤およびその製造中間体

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5869506A (en) * 1996-01-31 1999-02-09 Sumitomo Chemical Company, Limited Fluoropropene compound, an insecticide containing the same and an intermediate for production thereof
US7192965B2 (en) 2002-06-28 2007-03-20 Syngenta Crop Protection, Inc. 4-(3,3-dihalo-allyloxy)phenoxy alkyl derivatives
US7414064B2 (en) 2002-06-28 2008-08-19 Syngenta Crop Protection, Inc. 4-(3,3-dihalo-allyloxy) phenoxy alkyl derivatives
WO2005095330A1 (fr) * 2004-03-31 2005-10-13 Bayer Cropscience Ag Nouveaux derives de dichloropropene

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