WO2015025826A1 - Composé phényl éther substitué et agent de lutte antiparasitaire - Google Patents

Composé phényl éther substitué et agent de lutte antiparasitaire Download PDF

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WO2015025826A1
WO2015025826A1 PCT/JP2014/071593 JP2014071593W WO2015025826A1 WO 2015025826 A1 WO2015025826 A1 WO 2015025826A1 JP 2014071593 W JP2014071593 W JP 2014071593W WO 2015025826 A1 WO2015025826 A1 WO 2015025826A1
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group
halogen atom
substituted
atom
integer
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PCT/JP2014/071593
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English (en)
Japanese (ja)
Inventor
鈴木　潤
尾上　真治
英宏 田地野
竜太 大野
仁 若林
優太 小林
政時 野尻
美和 尾上
大悟 岡村
勝哉 山岸
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北興化学工業株式会社
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Priority claimed from JP2014086297A external-priority patent/JP2016185907A/ja
Application filed by 北興化学工業株式会社 filed Critical 北興化学工業株式会社
Publication of WO2015025826A1 publication Critical patent/WO2015025826A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring

Definitions

  • the present invention relates to a novel substituted phenyl ether compound and a pest control agent comprising the same as an active ingredient.
  • some of the widely used pest control agents are not only harmful to pests but also have strong toxicity to human livestock and fish and shellfish, and some are toxic to natural enemies.
  • Patent Document 1 describes a compound having a phenyl ether skeleton similar to the compound according to the present invention.
  • R 2 represents only a (C 1 -C 6 ) alkyl group, and the haloalkyl group and cycloalkylalkyl group of A in Formula (1) shown in the present invention are not described.
  • Patent Documents 2 and 3 describe diphenyl ether compounds useful as insecticides and acaricides.
  • Patent Documents 2 and 3 are compounds in which two benzene rings form an ether bond directly with an oxygen atom, but the compounds in which two benzene rings form an ether bond with an oxygen atom containing an alkylene chain as in the present invention. There is no description.
  • Patent Document 4 describes amidine compounds containing 3-substituted phenyl sulfide useful as insecticides and acaricides. Although the compound described in Patent Document 4 has an amidine skeleton at the 3-position of the benzene ring of phenyl sulfide, there is no description of a substituted phenyl ether skeleton as in the present invention. Patent Documents 5 and 6 describe 3-heterocyclic substituted phenyl sulfide compounds useful as insecticides and acaricides.
  • Patent Documents 5 and 6 each have a triazole ring and a pyrazole ring at the 3-position of the benzene ring of phenyl sulfide, there is no description of a substituted phenyl ether skeleton as in the present invention.
  • N-substituted aniline compounds exhibiting insecticidal activity similar to the present invention have been known so far.
  • the compound described in Patent Document 7 has an aminocarbonyl group substituted at the 3-position of aniline, there is no description of an aniline compound substituted with phenoxyalkyl as in the present invention.
  • Patent Document 8 describes an alkylphenyl sulfide compound having a pest control effect.
  • R 4 represents an alkyl group substituted with a phenyl group (the group may be substituted with R 6 ), and therefore shows a compound similar to the compound of the present invention.
  • no amino group is described in R 6 corresponding to the N-substituted aniline skeleton, which is a feature of the compound of the present invention.
  • Patent Document 9 describes a compound similar to the compound according to the present invention.
  • the general formula A and D ′′ in Patent Document 9 there is no description of a haloalkylthio group, a cycloalkylalkylthio group, a haloalkylsulfinyl group, a cycloalkylalkylsulfinyl group, or the like, and no description of insecticidal activity.
  • An object of the present invention is to provide a novel substituted phenyl ether compound having a safe and pest control effect and a pest control agent characterized by containing this as an active ingredient.
  • the substituted phenyl ether compound represented by the following formula (1) has an excellent control effect against pests, and completes the present invention. It came to.
  • A is a C 2 -C 5 haloalkyl group, a C 2 -C 5 haloalkenyl group, or an optionally substituted C 3 -C 8 cycloalkyl C 1 -C 4 alkyl group (the group is And may be mono-substituted or poly-substituted by a halogen atom or a C 1 -C 3 alkyl group.), N represents an integer of 0 to 2.
  • X 1 and X 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 alkoxy that may be substituted with a halogen atom.
  • X 1 and X 2 cannot simultaneously be hydrogen atoms.
  • Y is a hydrogen atom, a halogen atom, a nitro group, a cyano group, an amino group, a formyl group, an optionally C 1 ⁇ C 6 alkyl group optionally substituted by a halogen atom, which may C 1 be ⁇ C 6 alkoxy substituted with a halogen atom group, optionally substituted C 1 ⁇ C 6 alkylthio group with a halogen atom, a halogen atom with optionally substituted C 1 ⁇ C 6 alkylsulfinyl group, optionally substituted C 1 ⁇ C 6 alkylsulfonyl halogen atom Group, C 1 -C 6 alkylamino group, di-C 1 -C 6 alkylamino group, C 1 -C 6 alkylcarbonyl group, C 1 -C 6 alkoxycarbonyl group, C 1 -C 6 alkoxyiminomethyl group, halogen aryl group which may be substituted
  • An optionally substituted arylsulfonyl group (the group is a halogen atom, a cyano group, a C 1 -C 3 alkyl group, a C 1 -C 3 haloalkyl group, a C 1 -C 3 alkoxy group, a C 1 -C 3 halo group) Alkoxy group, C 1 -C 3 alkylthio group, C 1 -C 3 haloalkylthio group, C 1 -C 3 alkylsulfinyl group, C 1 -C 3 haloalkylsulfinyl group, C 1 -C 3 alkylsulfonyl group, C 1- A C 3 haloalkylsulfonyl group, a C 1 -C 3 alkylcarbonyl group, or a C 1 -C 3 alkoxycarbonyl group may be mono- or polysubstituted), or a C 7 -C optionally substituted with
  • Y When m represents an integer of 2 to 5, Y may be the same or different. Further, when m represents an integer of 2 or more, and bind adjacent each other in the Y, -OCH 2 O -, - OCF 2 O -, - OCH 2 CH 2 O -, - OCF 2 CH 2 O-, Alternatively, —OCF 2 CF 2 O— may be represented.
  • R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C that may be substituted with a halogen atom.
  • R 1 and R 2 on different carbon atoms may be the same or different.
  • R 1 and R 2 on the same carbon atom can be each represented by ( ⁇ O) or ( ⁇ S) by being bonded to one oxygen atom or sulfur atom.
  • R 1 and R 2 on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group.
  • R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
  • Z represents an oxygen atom, a sulfur atom, a sulfinyl group, or a sulfonyl group, and q represents an integer of 0 or 1. However, p and q cannot be 1 at the same time.
  • the second aspect of the present invention relates to a pest control agent containing a substituted phenyl ether compound represented by the above formula (1).
  • the third aspect of the invention according to the present application relates to a production intermediate represented by the following formula (2).
  • A is an optionally substituted C 3 -C 8 cycloalkylmethyl group (the group may be mono-substituted or poly-substituted by a fluorine atom or a C 1 -C 3 alkyl group).
  • N represents an integer of either 0 or 1.
  • X 1 represents a C 1 -C 4 alkyl group
  • X 2 represents a hydrogen atom, a halogen atom, or a C 1 -C 4 alkyl group.
  • the fourth aspect of the invention according to the present application relates to an N-substituted aniline compound represented by the following formula (1-6).
  • a 100 represents a C 2 -C 5 haloalkyl group or a C 3 -C 6 cycloalkyl C 1 -C 3 alkyl group, and n represents an integer of 0 to 2 .
  • X 101 and X 102 are each independently a hydrogen atom, a halogen atom, a cyano group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 6 that may be substituted with a halogen atom.
  • An alkoxy group is shown.
  • X 101 and X 102 cannot simultaneously be hydrogen atoms.
  • Y 100 represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, a C 1 -C 6 alkoxy group that may be substituted with a halogen atom, optionally substituted C 1 ⁇ C 6 alkylthio group with a halogen atom, a halogen atom with optionally substituted C 1 ⁇ C 6 alkylsulfinyl group, optionally substituted C 1 ⁇ C 6 alkylsulfonyl group with a halogen atom, A C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, or a C 1 -C 6 alkoxyiminomethyl group, and v represents an integer of 1 to 4.
  • R 101a and R 102a are each independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, an optionally C 1 ⁇ C 6 alkyl group optionally substituted by a halogen atom or C 1 ⁇ optionally substituted by a halogen atom, It shows the C 4 alkoxy groups. Further, R 101a and R 102a on the same carbon atom can be each represented by ( ⁇ O) or ( ⁇ S) by being bonded to one oxygen atom or sulfur atom.
  • R 101a and R 102a on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group.
  • R 101a and R 102a on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
  • R 101b and R 102b each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl group that may be substituted with a halogen atom, or a C 1 -C 4 alkoxy group that may be substituted with a halogen atom.
  • U represents an integer of either 0 or 1.
  • the fifth aspect of the present invention relates to a pest control agent comprising an N-substituted aniline compound represented by the above formula (1-6).
  • the sixth aspect of the present invention relates to a compound represented by the following formula (3), which is a production intermediate of the N-substituted aniline compound represented by the above formula (1-6).
  • G represents CO 2 R 103 (R 103 represents a C 1 -C 4 alkyl group), or CH 2 OR 104 (R 104 represents a hydrogen atom or a C atom optionally substituted with a halogen atom). 1 -C 4 alkylsulfonyl group, or arylsulfonyl group optionally substituted with C 1 -C 4 alkyl group.
  • Y 101 and Y 102 each independently represent a hydrogen atom (except when G represents CO 2 R 3 ), a halogen atom, or a C 1 -C 4 alkyl group that may be substituted with a halogen atom. .
  • W 3 and W 4 each independently represent a hydrogen atom, a C 1 -C 6 alkylcarbonyl group that may be substituted with a halogen atom, a C 1 -C 6 alkoxycarbonyl group, or a C that may be substituted with a halogen atom. 1 to C 6 alkylsulfonyl group.
  • the substituted phenyl ether compound according to the present invention has a substituted phenyl-substituted alkyl ether skeleton represented by the following formula (1) as a basic skeleton.
  • examples of the halogen atom or the halogen atom as a substituent include each element of fluorine, chlorine, bromine or iodine.
  • the number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • the C 2 -C 5 haloalkyl group represented by A includes a 2-fluoroethyl group, a 1-chloroethyl group, a 2-chloroethyl group, a 1-bromoethyl group, a 2-bromoethyl group, 2, 2-difluoroethyl group, 1,2-dichloroethyl group, 2,2-dichloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 1,1,2,2 -Tetrafluoroethyl group, pentafluoroethyl group, 2-bromo-2-chloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 1-chloro-1,2,2,2-tetra Fluoroethyl group, 1-chloropropyl group, 2-chloropropyl group, 3-chlor
  • the C 2 -C 5 haloalkenyl group represented by A includes bromovinyl group, chlorovinyl group, 3,3-dichloro-2-propenyl group, 3,3,3-trifluoro- 1-propenyl group 4,4-difluoro-3-butenyl group, 3,4,4-trifluoro-3-butenyl group, and the like, more preferably 3,3,3-trifluoro-1-propenyl group Is mentioned.
  • C 3 ⁇ C 8 cycloalkyl C 1 ⁇ C 4 alkyl group moiety of the optionally substituted C 3 be ⁇ C 8 cycloalkyl C 1 ⁇ C 4 alkyl group represented by A, Cyclopropylmethyl group, 1-cyclopropylethyl group, 2-cyclopropylethyl group, 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclo Propylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, cyclobutylmethyl group, 1-cyclobutylethyl group, 2-cyclobutylethyl group, cyclopentylmethyl group, cyclohexylmethyl group, cycloheptylmethyl group, A cyclooctylmethyl group is mentioned, More preferably, a cyclopropylmethyl group, 1-
  • the halogen atom as a substituent has the same definition as described above, and examples of the C 1 -C 3 alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and more preferably a fluorine atom or A methyl group is mentioned.
  • n any integer of 0-2.
  • the oxygen atom (O) is not added to the sulfur atom (S)
  • the halogen atom have the same definition as above, C 1 ⁇ C 6 alkyl group portion of the good C 1 ⁇ C 6 alkyl group optionally substituted by a halogen atom represented by X 1 and X 2 As methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl Group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group.
  • the formula (1) as the C 1 ⁇ C 6 alkoxy group portion of which may C 1 be ⁇ C 6 alkoxy group substituted with a halogen atom represented by X 1 and X 2, a methoxy group, an ethoxy radical, n -Propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.
  • examples of the C 3 -C 6 cycloalkyl group represented by X 1 and X 2 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, and more preferably cyclopropyl group Groups.
  • examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by X 1 or X 2 include a phenyl group and a naphthyl group, and more preferably a phenyl group. Can be mentioned.
  • the halogen atom represented by Y has the same definition as above, preferably a fluorine atom, a chlorine atom, or a bromine atom, more preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom. Is preferred.
  • the C 1 ⁇ C 6 alkoxy group moiety of the optionally C 1 ⁇ C 6 alkoxy group optionally substituted by a halogen atom represented by Y a methoxy group, an ethoxy group, n- propoxy group, An i-propoxy group, an n-butoxy group, an i-butoxy group, a sec-butoxy group, a tert-butoxy group, and the like are preferable, and a methoxy group or an ethoxy group is more preferable.
  • C 1 ⁇ C 6 alkylthio moiety good C 1 ⁇ C 6 alkylthio group optionally substituted by a halogen atom represented by Y, methylthio group, ethylthio group, n- propylthio group
  • a halogen atom represented by Y examples include i-propylthio group, n-butylthio group, i-butylthio group, sec-butylthio group, and tert-butylthio group, and more preferable examples include methylthio group and ethylthio group.
  • the formula (1) as the C 1 ⁇ C 6 alkylsulfinyl group moiety of the optionally substituted C 1 ⁇ C 6 alkylsulfinyl group by a halogen atom represented by Y, methylsulfinyl group, ethylsulfinyl radical, n -Propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, more preferably methylsulfinyl group or ethylsulfinyl group Can be mentioned.
  • the formula (1) as the C 1 ⁇ C 6 alkylsulfonyl group moiety of optionally substituted C 1 ⁇ C 6 alkylsulfonyl group by a halogen atom represented by Y, methylsulfonyl group, ethylsulfonyl radical, n -Propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, more preferably methylsulfonyl group or ethylsulfonyl group Can be mentioned.
  • the C 1 -C 6 alkylamino group represented by Y is a methylamino group, ethylamino group, n-propylamino group, i-propylamino group, n-butylamino group, i -Butylamino group, sec-butylamino group, tert-butylamino group are preferable, and methylamino group or ethylamino group is more preferable.
  • the di-C 1 -C 6 alkylamino group represented by Y includes a dimethylamino group, a methylethylamino group, a diethylamino group, a di-n-propylamino group, a methyl n-propylamino group, Examples include ethyl n-propylamino group, di-i-propylamino group, di-n-butylamino group, di-i-butylamino group, disec-butylamino group, and ditert-butylamino group, and more preferred is dimethyl An amino group or a diethylamino group is mentioned.
  • examples of the C 1 -C 6 alkylcarbonyl group represented by Y include an acetyl group, a propionyl group, a butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group, and the like. Includes an acetyl group.
  • the number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 1 -C 6 alkoxycarbonyl group represented by Y is a methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, tert -Butoxycarbonyl group, etc. are mentioned, More preferably, a methoxycarbonyl group or an ethoxycarbonyl group is mentioned.
  • the number of carbon atoms of the alkoxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 1 -C 6 alkoxyiminomethyl group represented by Y includes a methoxyimino group, an ethoxyimino group, an n-propoxyimino group, an i-propoxyimino group, an n-butoxyimino group, Examples thereof include a tert-butoxyimino group, and more preferably a methoxyimino group.
  • examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by Y include a phenyl group and a naphthyl group, and more preferably a phenyl group.
  • examples of the aryloxy group moiety of the optionally substituted aryloxy group represented by Y include a phenoxy group and a naphthyloxy group, and more preferably a phenoxy group.
  • Halogen atom as a substituent have the same definition as above, methyl group is a C 1 ⁇ C 3 alkyl group, an ethyl group, n- propyl group, i- propyl group and the like, C 1 ⁇ C 3 haloalkyl group Examples thereof include a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group and the like, and examples of the C 1 -C 3 alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, and an i-propoxy group.
  • Examples of the C 1 -C 3 haloalkoxy group include a difluoromethoxy group, a trifluoromethoxy group, and a 2,2,2-trifluoroethoxy group, and examples of the C 1 -C 3 alkylthio group include a methylthio group.
  • C 1 -C 3 alkylsulfinyl groups include difluoromethylsulfinyl group, trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group and the like, and C 1 -C 3 Examples of the alkylsulfonyl group include a methylsulfonyl group.
  • examples of the arylthio group part of the optionally substituted arylthio group represented by Y include a phenylthio group, a naphthylthio group, and the like, more preferably a phenylthio group.
  • the group C 1 -C 3 alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.
  • examples of the arylsulfinyl group portion of the optionally substituted arylsulfinyl group represented by Y include a phenylsulfinyl group, a naphthylsulfinyl group, and the like, more preferably a phenylsulfinyl group. .
  • the group C 1 -C 3 alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.
  • examples of the arylsulfonyl group moiety of the optionally substituted arylsulfonyl group represented by Y include a phenylsulfonyl group and a naphthylsulfonyl group, and more preferably a phenylsulfonyl group.
  • the group C 1 -C 3 alkoxycarbonyl group has the same definition as above, and more preferably a fluorine atom or a trifluoromethyl group.
  • the C 7 ⁇ C 11 aralkyloxy group moiety of the optionally substituted C 7 be ⁇ C 11 aralkyloxy group with a halogen atom represented by Y, benzyloxy group, phenethyloxy group and the like More preferably, a benzyloxy group is mentioned.
  • m represents an integer of 1 to 5.
  • Y is added to any one of the five carbon atoms (C) constituting the phenyl group.
  • Y is added to any two or three or four of the carbon atoms (C), and when m is 5, all of the carbon atoms (C) are added. Y is added.
  • Y and m those in which Y is a fluorine atom, m is 3, and a fluorine atom is added to the 3, 4, and 5 positions of the phenyl group are preferable.
  • the halogen atom have the same definition as above, C 1 ⁇ C 6 alkyl group portion of the good C 1 ⁇ C 6 alkyl group optionally substituted by a halogen atom represented by R 1 and R 2 As methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl Group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group.
  • examples of the C 3 -C 6 cycloalkyl group represented by R 1 and R 2 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and the like, and more preferably cyclopropyl group Groups.
  • examples of the C 1 -C 4 alkylcarbonyloxy group represented by R 1 and R 2 include acetyloxy group, propionyloxy group, butyryloxy group, i-butyryloxy group, pivaloyloxy group and the like. More preferred is an acetyloxy group.
  • the number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • p shows the integer in any one of 1-5.
  • each represents a methylene chain, an ethylene chain, a propylene chain, a butylene chain, or a pentylene chain.
  • R 1 and R 2 on different carbon atoms may be the same or different.
  • R 1 and R 2 on the same carbon atom can be each represented by ( ⁇ O) or ( ⁇ S) by being bonded to one oxygen atom or sulfur atom.
  • R 1 and R 2 on the same carbon atom can be bonded simultaneously to represent a C 1 -C 4 alkoxyimino group, such as a methoxyimino group.
  • R 1 and R 2 on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
  • Z represents an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group, more preferably an oxygen atom.
  • q represents an integer of 0 or 1. However, p and q cannot be 1 at the same time.
  • Z is not included in the formula (1), and when q is 1, any atom of Z is added.
  • the N-substituted aniline compound according to the present invention has a substituted phenoxyalkyl-substituted aniline skeleton represented by the following formula (1-6) as a basic skeleton.
  • examples of the halogen atom or the halogen atom as a substituent include each element of fluorine, chlorine, bromine or iodine.
  • the number of halogen atoms as substituents may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • the C 2 -C 5 haloalkyl group represented by A 100 is a 2-fluoroethyl group, 1-chloroethyl group, 2-chloroethyl group, 1-bromoethyl group, 2-bromoethyl group 2,2-difluoroethyl group, 1,2-dichloroethyl group, 2,2-dichloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, 1,1, 2,2-tetrafluoroethyl group, pentafluoroethyl group, 2-bromo-2-chloroethyl group, 2-chloro-1,1,2,2-tetrafluoroethyl group, 1-chloro-1,2,2, 2-tetrafluoroethyl group, 1-chloropropyl group, 2-chloropropyl group, 3-chloropropyl group, 2-brom
  • the C 3 -C 6 cycloalkyl C 1 -C 3 alkyl group represented by A 100 includes a cyclopropylmethyl group, a 1-cyclopropylethyl group, a 2-cyclopropylethyl group 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclopropylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, Examples thereof include a cyclobutylmethyl group, a 1-cyclobutylethyl group, a 2-cyclobutylethyl group, a cyclopentylmethyl group, and a cyclohexylmethyl group, and more preferably a cyclopropylmethyl group.
  • n represents an integer of 0 to 2.
  • the oxygen atom (O) is not added to the sulfur atom (S)
  • C 1 ⁇ C 6 alkyl substituted C 1 may be ⁇ C 6 alkyl group by a halogen atom
  • the group part includes methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like are preferable, and methyl group is more preferable.
  • the halogen atom represented by Y 100 represents the same definition as above, as a C 1 ⁇ C 6 alkyl group portion of the optionally substituted C 1 ⁇ C 6 alkyl group by a halogen atom Is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, 2-pentyl , 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group.
  • C 1 ⁇ C 6 alkylthio moiety good C 1 ⁇ C 6 alkylthio group optionally substituted by a halogen atom represented by Y 100, methylthio group, ethylthio group, n- Examples thereof include a propylthio group, an i-propylthio group, an n-butylthio group, an i-butylthio group, a sec-butylthio group, and a tert-butylthio group, and more preferably a methylthio group or an ethylthio group.
  • C 1 ⁇ C 6 alkylsulfinyl group moiety of the optionally substituted C 1 ⁇ C 6 alkylsulfinyl group by a halogen atom represented by Y 100 are methylsulfinyl group, ethylsulfinyl Group, n-propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, more preferably methylsulfinyl group or ethyl A sulfinyl group is mentioned.
  • the C 1 -C 6 alkylsulfonyl group moiety of the C 1 -C 6 alkylsulfonyl group which may be substituted with a halogen atom represented by Y 100 includes a methylsulfonyl group, ethylsulfonyl Group, n-propylsulfonyl group, i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, more preferably methylsulfonyl group or ethyl A sulfonyl group is mentioned.
  • examples of the C 1 -C 6 alkylcarbonyl group represented by Y 100 include an acetyl group, a propionyl group, a butyryl group, an i-butyryl group, a valeryl group, and a pivaloyl group. More preferred is an acetyl group.
  • the number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 1 -C 6 alkoxycarbonyl group represented by Y 100 includes a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and an n-butoxycarbonyl group.
  • the number of carbon atoms of the alkoxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 1 -C 6 alkoxyiminomethyl group represented by Y 100 includes a methoxyiminomethyl group, an ethoxyiminomethyl group, an n-propoxyiminomethyl group, and an i-propoxyiminomethyl group. N-butoxyiminomethyl group, tert-butoxyiminomethyl group and the like, more preferably methoxyiminomethyl group.
  • v represents any integer of 1 to 4. If v is a 1, Y 100 is added to any one of the six carbon atoms constituting the phenyl group (C). When v is 2 to 4, Y 100 is added to any two, three or four of the carbon atoms (C).
  • C 1 ⁇ C 6 alkyl substituted C 1 may be ⁇ C 6 alkyl group by a halogen atom
  • the group part includes methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group .
  • R 101a and good C 1 ⁇ C 4 alkoxy group optionally substituted by a halogen atom represented by R 102a, a methoxy group, an ethoxy group N-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, sec-butoxy group, tert-butoxy group and the like, more preferably methoxy group.
  • R 101a and R 102a on the same carbon atom can be each represented by ( ⁇ O) or ( ⁇ S) by being bonded to one oxygen atom or sulfur atom.
  • R 101a and R 102a on the same carbon atom can be bonded at the same time to represent a C 1 -C 4 alkoxyimino group, such as a methoxyimino group.
  • R 101a and R 102a on the same carbon atom can be bonded to each other to form a 3-membered ring, 4-membered ring, 5-membered ring or 6-membered ring with 2 to 5 alkylene groups.
  • C 1 ⁇ C 6 alkyl substituted C 1 may be ⁇ C 6 alkyl group by a halogen atom
  • the group part includes methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, neopentyl group, 2 -Pentyl group, 3-pentyl group, tert-pentyl group, n-hexyl group, i-hexyl group, 2-hexyl group, 3-hexyl group and the like, more preferably methyl group or ethyl group .
  • the C 3 to C 6 cycloalkyl group represented by W 1 includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, and 2,2-dimethylcyclo A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned, More preferably, a cyclopropyl group is mentioned.
  • the C 3 -C 6 cycloalkyl C 1 -C 3 alkyl group represented by W 1 includes a cyclopropylmethyl group, a 1-cyclopropylethyl group, a 2-cyclopropylethyl group 1-cyclopropylpropyl group, 2-cyclopropylpropyl group, 3-cyclopropylpropyl group, 1-cyclopropylbutyl group, 2-cyclopropylbutyl group, 3-cyclopropylbutyl group, 4-cyclopropylbutyl group, Examples thereof include a cyclobutylmethyl group, a 1-cyclobutylethyl group, a 2-cyclobutylethyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a cycloheptylmethyl group, and a cyclooctylmethyl group, and more preferably a cyclopropylmethyl group. It is done
  • the C 1 ⁇ C 6 alkyl group portion of the optionally substituted C 1 ⁇ C 6 alkyl group by a halogen atom represented by W 1 an acetyl group, a propionyl group, A butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group and the like can be mentioned, and an acetyl group is more preferred.
  • the number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 2 ⁇ C 6 alkenyl group moiety of the optionally substituted C 2 be ⁇ C 6 alkenyl group by halogen atom represented by W 1, acryloyl group, methacryloyl group, etc. And more preferably an acryloyl group.
  • the number of carbon atoms of the alkenylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • C 2 ⁇ C 6 alkynyl group moiety of the optionally substituted C 2 be ⁇ C 6 alkynyl group with halogen atoms represented by W 1
  • Puropioriru group, Mechirupuropio A ryl group etc. are mentioned,
  • a propioyl group is mentioned more suitably.
  • the number of carbon atoms of the alkynylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 3 ⁇ C 6 cycloalkyl group moiety of the optionally substituted C 3 be ⁇ C 6 cycloalkyl group with a halogen atom represented by W 1, cyclopropanecarbonyl group 1-methylcyclopropanecarbonyl group, 2-methylcyclopropanecarbonyl group, 2,2-dimethylcyclopropanecarbonyl group, cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group and the like, more preferably cyclopropane A carbonyl group is mentioned.
  • the number of carbon atoms of the cycloalkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • a C 3 -C 6 cycloalkyl C 1 -C 3 alkylcarbonyl group C 3 -C 6 cycloalkyl C 1 -C optionally substituted with a halogen atom represented by W 1
  • the 3- alkylcarbonyl group include cyclopropaneacetyl, cyclopropanepropionyl, 2-cyclopropaneacetyl, 1-methylcyclopropaneacetyl, 2-methylcyclopropaneacetyl, 2,2-dimethylcyclopropaneacetyl , Cyclobutane acetyl group, cyclopentane acetyl group, cyclohexane acetyl group, and the like, more preferably cyclopropane acetyl group.
  • the number of carbon atoms of the cycloalkylalkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbony
  • C 1 - C 6 alkoxycarbonyl group portion - good C 1 optionally substituted by a halogen atom C 6 alkoxycarbonyl group represented by W 1, a methoxycarbonyl group, an ethoxycarbonyl Group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxycarbonyl group , 2-pentoxycarbonyl group, 3-pentoxycarbonyl group and the like, more preferably tert-butoxycarbonyl group.
  • the number of carbon atoms of the alkoxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 2 ⁇ C 6 alkenyloxycarbonyl group moiety of the optionally substituted C 2 be ⁇ C 6 alkenyloxycarbonyl group with a halogen atom represented by W 1, vinyl oxycarbonyl group 1-propenyloxycarbonyl group, 2-propenyloxycarbonyl group, 1-butenyloxycarbonyl group, 2-butenyloxycarbonyl group, 3-butenyloxycarbonyl group and the like, more preferably vinyloxycarbonyl Groups.
  • the number of carbon atoms of the alkenyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 2 ⁇ C 6 alkynyloxy group moiety of the optionally substituted C 2 be ⁇ C 6 alkynyloxy group with the halogen atom represented by W 1, ethynyl oxycarbonyl group 1-propynyloxycarbonyl group, propargyloxycarbonyl group, 1-butynyloxycarbonyl group, 2-butynyloxycarbonyl group, 3-butynyloxycarbonyl group, 1-methyl-2-propynyloxycarbonyl group, 2- Examples thereof include a methyl-3-butynyloxycarbonyl group, and a propargyloxycarbonyl group is more preferable.
  • the number of carbon atoms of the alkynyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 3 ⁇ C 6 cycloalkyl alkyloxycarbonyl moiety of the optionally substituted C 3 be ⁇ C 6 cycloalkyloxy group with a halogen atom represented by W 1, cyclopropyl Oxycarbonyl group, 1-methylcyclopropyloxycarbonyl group, 2-methylcyclopropyloxycarbonyl group, 2,2-dimethylcyclopropyloxycarbonyl group, cyclobutyloxycarbonyl group, cyclopentyloxycarbonyl group, cyclohexyloxycarbonyl group, etc. And a cyclopropyloxycarbonyl group is more preferable.
  • the number of carbon atoms of the cycloalkyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 3 alkyloxycarbonyl group include cyclopropylmethyloxycarbonyl group, 1-methylcyclopropylmethyloxycarbonyl group, 2-methylcyclopropylmethyloxycarbonyl group, 2,2-dimethylcyclopropylmethyloxycarbonyl group, cyclo A butylmethyloxycarbonyl group, a cyclopentyloxymethylcarbonyl group, a cyclohexylmethyloxycarbonyl group, etc.
  • a cyclopropylmethyloxycarbonyl group is mentioned.
  • the number of carbon atoms of the cycloalkylalkyloxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • the C 1 ⁇ C 6 alkyl amino group moiety of the optionally substituted C 1 ⁇ C 6 alkyl amino group with a halogen atom represented by W 1, methylaminocarbonyl group Ethylaminocarbonyl group, n-propylaminocarbonyl group, i-propylaminocarbonyl group, n-butylaminocarbonyl group, i-butylaminocarbonyl group, sec-butylaminocarbonyl group, tert-butylaminocarbonyl group, n- A pentylaminocarbonyl group etc. are mentioned, A methylaminocarbonyl group is mentioned more suitably.
  • the number of carbon atoms of the alkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • di C 1 ⁇ C 6 alkyl amino group moiety of a substituted di C 1 may be ⁇ C 6 alkyl amino group with a halogen atom represented by W 1 is dimethylamino Carbonyl group, methylethylaminocarbonyl group, diethylaminocarbonyl group, di-n-propylaminocarbonyl group, methyl n-propylaminocarbonyl group, ethyl n-propylaminocarbonyl group, di-propylaminocarbonyl group, di-n-butylamino Examples thereof include a carbonyl group, a dii-butylaminocarbonyl group, a disec-butylaminocarbonyl group, a ditert-butylaminocarbonyl group, and more preferably a dimethylaminocarbonyl group.
  • the number of carbon atoms of the dialkylaminocarbonyl group represented by C is the number of carbon
  • the C 3 -C 6 cycloalkylaminocarbonyl group of the C 3 -C 6 cycloalkylaminocarbonyl group which may be substituted with a halogen atom represented by W 1 includes cyclopropyl Aminocarbonyl group, 1-methylcyclopropylaminocarbonyl group, 2-methylcyclopropylaminocarbonyl group, 2,2-dimethylcyclopropylaminocarbonyl group, cyclobutylaminocarbonyl group, cyclopentylaminocarbonyl group, cyclohexylaminocarbonyl group, etc. And a cyclopropylaminocarbonyl group is more preferable.
  • the number of carbon atoms of the cycloalkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • a C 3 to C 6 cycloalkyl C 1 to C 3 alkylaminocarbonyl group C 3 to C 6 cycloalkyl C 1 to C 1 optionally substituted with a halogen atom represented by W 1
  • the C 3 alkylaminocarbonyl group include cyclopropylmethylaminocarbonyl group, 1-methylcyclopropylmethylaminocarbonyl group, 2-methylcyclopropylmethylaminocarbonyl group, 2,2-dimethylcyclopropylmethylaminocarbonyl group, cyclo A butylmethylaminocarbonyl group, a cyclopentylaminomethylcarbonyl group, a cyclohexylmethylaminocarbonyl group, etc.
  • a cyclopropylmethylaminocarbonyl group is mentioned, More preferably, a cyclopropylmethylaminocarbonyl group is mentioned.
  • the number of carbon atoms of the cycloalkylalkylaminocarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • C 3 ⁇ C 6 cycloalkyl sulfonyl group moiety of the optionally substituted C 3 be ⁇ C 6 cycloalkyl sulfonyl group with a halogen atom represented by W 1, cyclopropanesulfonyl group 1-methylcyclopropanesulfonyl group, 2-methylcyclopropanesulfonyl group, 2,2-dimethylpropanesulfonyl group, cyclobutanecarbonyl group, cyclopentanecarbonyl group, cyclohexanecarbonyl group and the like, more preferably cyclopropanesulfonyl group Groups.
  • a C 3 -C 6 cycloalkyl C 1 -C 3 alkylsulfonyl group C 3 -C 6 cycloalkyl C 1 -C optionally substituted with a halogen atom represented by W 1
  • the 3- alkylsulfonyl group include cyclopropylmethylsulfonyl, 1-methylcyclopropylmethylsulfonyl, 2-methylcyclopropylmethylsulfonyl, 2,2-dimethylcyclopropylmethylsulfonyl, cyclobutylmethylsulfonyl, cyclopentyl A sulfonyl group, a cyclohexylmethylsulfonyl group, etc. are mentioned, More preferably, a cyclopropylmethylsulfonyl group is mentioned.
  • di C 1 ⁇ C 6 alkylaminosulfonyl group moiety of a substituted di C 1 may be ⁇ C 6 alkylaminosulfonyl group with a halogen atom represented by W 1 is dimethylamino Sulfonyl group, methylethylaminosulfonyl group, diethylaminosulfonyl group, di-n-propylaminosulfonyl group, methyl n-propylaminosulfonyl group, ethyl n-propylaminosulfonyl group, dii-propylaminosulfonyl group, di-n-butylamino Examples include a sulfonyl group, a dii-butylaminosulfonyl group, a disec-butylaminosulfonyl group, a ditert-butylaminosulfonyl group, and more preferably a sulfonyl
  • examples of the aryl group portion of the aryl group which may be substituted with a halogen atom represented by W 1 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, and the like. A phenyl group is preferable.
  • examples of the arylcarbonyl group portion of the arylcarbonyl group which may be substituted with a halogen atom represented by W 1 include a benzoyl group, a 1-naphthoyl group, and a 2-naphthoyl group. More preferred is a benzoyl group.
  • the aryloxycarbonyl group portion of the aryloxycarbonyl group which may be substituted with a halogen atom represented by W 1 includes a phenoxycarbonyl group, a 1-naphthyloxycarbonyl group, and 2-naphthyl.
  • An oxycarbonyl group etc. are mentioned, More preferably, a phenoxycarbonyl group is mentioned.
  • the arylaminocarbonyl group part of the arylaminocarbonyl group which may be substituted with a halogen atom represented by W 1 includes a phenylaminocarbonyl group, a 1-naphthylaminocarbonyl group, 2- A naphthylaminocarbonyl group etc. are mentioned, A phenylaminocarbonyl group is mentioned more suitably.
  • examples of the arylsulfonyl group part of the optionally substituted arylsulfonyl group represented by W 1 include a benzenesulfonyl group, a 1-naphthalenesulfonyl group, a 2-naphthalenesulfonyl group, and the like. More preferred is a benzenesulfonyl group.
  • the halogen atom as a substituent has the same definition as above, and examples of the C 1 -C 3 alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and the like, and more preferably a chlorine atom or A methyl group is mentioned.
  • the C 3 -C 6 cycloalkyl group represented by W 2 includes a cyclopropyl group, a 1-methylcyclopropyl group, a 2-methylcyclopropyl group, and 2,2-dimethylcyclo A propyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned, More preferably, a cyclopropyl group is mentioned.
  • the C 1 -C 6 alkoxy C 1 -C 3 alkyl group represented by W 2 includes a methoxymethyl group, an ethoxymethyl group, an n-propoxymethyl group, a methoxyethyl group, and the like. More preferably, a methoxymethyl group is mentioned.
  • the C 1 ⁇ C 6 alkyl group portion of the optionally substituted C 1 ⁇ C 6 alkyl group by a halogen atom represented by W 2 an acetyl group, a propionyl group, A butyryl group, an i-butyryl group, a valeryl group, a pivaloyl group and the like can be mentioned, and an acetyl group is more preferred.
  • the number of carbon atoms of the alkylcarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • C 1 - C 6 alkoxycarbonyl group portion - good C 1 optionally substituted by a halogen atom C 6 alkoxycarbonyl group represented by W 2, a methoxycarbonyl group, an ethoxycarbonyl Group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentoxycarbonyl group, neopentoxycarbonyl group , 2-pentoxycarbonyl group, 3-pentoxycarbonyl group and the like, more preferably tert-butoxycarbonyl group.
  • the number of carbon atoms of the alkoxycarbonyl group represented by C is the number of carbon atoms excluding the carbon atoms of the carbonyl group.
  • examples of the arylcarbonyl group portion of the arylcarbonyl group which may be substituted with a halogen atom represented by W 2 include a benzoyl group, a 1-naphthoyl group, and a 2-naphthoyl group. More preferred is a benzoyl group.
  • the arylsulfonyl group moiety of the optionally substituted arylsulfonyl group represented by W 2 includes a benzenesulfonyl group, a 1-naphthalenesulfonyl group, a 2-naphthalenesulfonyl group, and the like. More preferred is a benzenesulfonyl group.
  • the halogen atom as a substituent has the same definition as above, and examples of the C 1 -C 3 alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, and the like, and more preferably a chlorine atom or A methyl group is mentioned.
  • N-substituted aniline compounds represented by formula (1-6) are shown in Tables 10 to 11, and typical examples of aniline compounds represented by formula (3) are shown in Table 12. It is not limited to compounds. In addition, these compounds include compounds including optical isomers, E isomers, and Z isomers. The compound number is referred to in the following description.
  • surface represents each applicable group as follows.
  • “Me” is a methyl group
  • “Et” is an ethyl group
  • “Pr” is a propyl group
  • “n-Pr” is a normal propyl group
  • “i-Pr” is an isopropyl group
  • “Bu” is a butyl group
  • “n-Pr” “Bu” is a normal butyl group
  • “Pen” is a pentyl group
  • “n-Pen” is a normal pentyl group
  • “Hex” is a hexyl group
  • “n-Hex” is a normal hexyl group
  • “Hep” is a heptyl group
  • “s -Bu is a secondary butyl group
  • i-Bu is an isobutyl group
  • t-Bu is a tertiary butyl group
  • c-Pr is a cyclopropyl group
  • Table 1 represents a specific example of the formula (1) in which q is 0 and p is 1
  • Table 2 represents a specific example of the formula (1) in which q is 0 and p is 2
  • Table 3 Represents a specific example of the formula (1) in which q is 0 and p is 3
  • Table 4 represents a specific example of the formula (1) in which q is 0 and p is 4
  • Table 5 represents the q Represents a specific example of the formula (1) in which 0 is 0 and p is 5
  • Table 6 represents a specific example of the formula (1) in which q is 1 and p is 2
  • Table 7 shows that q is 1.
  • Table 8 represents a specific example of Formula (1) in which q is 1 and p is 4
  • Table 9 represents a specific example of Formula (2).
  • R 1a , R 1b , R 1c , R 1d , and R 1e represent R 1 specifying the substitution position on the alkylene chain
  • R 2a , R 2b , R 2c , R 2d , and R 2e are substitution positions on the alkylene chain R 2 in which is specified.
  • Table 10 shows a specific example of formula (1-6) where u is 0, Table 11 shows a specific example of formula (1-6) where u is 1, and Table 12 shows a specific example of formula (3) Represents.
  • 3-F indicates that a fluorine atom is substituted at the 3-position of the phenyl group
  • 3,4,5-F 3 indicates the 3,4 of the phenyl group.
  • compounds represented by the following formula (1-1) are preferable, and particularly preferred representative examples include compounds represented by the following formula (1-2).
  • n represents an integer of 0 or 1
  • X 2 represents a fluorine atom, a chlorine atom, a bromine atom, or a cyano group
  • R 1a and R 2a are each independently A fluorine atom, a hydroxyl group, an ethyl group, an isopropyl group, an isobutyl group, a methoxy group, an acetyloxy group
  • n represents an integer of 0 or 1
  • X 2 represents a fluorine atom or a chlorine atom.
  • the compound according to the present invention represented by the above formula (1) can be produced according to the production method shown below, but is not limited to these methods.
  • reaction step 1 (In the above formula, A, X 1 , X 2 , Y, R 1 , R 2 , Z, m, p, q have the same meaning as the substituted phenyl ether compound represented by the above formula (1), and n is 1 or 2 is shown.)
  • the compound represented by the formula (1c) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (1b) with an oxidizing agent.
  • the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI DuPont; trade name; peroxohydrogensulfate Potassium-containing substances), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like.
  • Preferred are m-chloroperbenzoic acid and hydrogen peroxide.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; pentane and hexane Aliphatic hydrocarbons such as cyclohexane and cycloheptane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid, water, or a mixed solvent thereof.
  • ethers such as dieth
  • L represents a leaving group such as a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, an arylsulfonyloxy group, A, X 1 , X 2 , Y, R 1 , R 2 , Z, m, p, and q have the same meaning as described above, and n represents an integer of 0 to 2.
  • the compound represented by the formula (1) according to the present invention includes, for example, a compound represented by the above formula (2a) and a compound represented by the above formula (4) in the presence of a base, if necessary. It can manufacture by making it react in presence.
  • the raw material represented by the above formula (4) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.
  • Examples of the base used in this reaction include bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine.
  • bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine.
  • bases such as potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, and pyridine.
  • Preferred are potassium carbonate, triethylamine, potassium hydroxide, sodium hydroxide and the like.
  • Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide, dichloromethane, or a mixture of water and an organic solvent is preferred.
  • reaction step 3 (In the above formula, A, X 1 , X 2 , Y, R 1 , R 2 , Z, n, m, p, q have the same meaning as described above.)
  • the compound represented by the formula (1) according to the present invention is, for example, Bulletin of the Chemical Society of Japan, 1967, p. 936, Bulletin of the Chemical Society of Japan, 1967, p. According to the method described in 2380, the compound represented by the above formula (2a) and the compound represented by the above formula (5) can be produced by Mitsunobu reaction.
  • the raw material represented by the above formula (5) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.
  • Examples of the phosphorus compound used in this reaction include triphenylphosphine, tri-n-butylphosphine, tritert-butylphosphine, phenoxydiphenylphosphine, and the like. Preferred are triphenylphosphine and phenoxydiphenylphosphine.
  • Examples of the azodicarboxylic acid ester used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate. Preferred is diethyl azodicarboxylate.
  • solvent used in this reaction examples include ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated carbonization such as dichloromethane, chloroform and 1,2-dichloroethane.
  • Hydrogens aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane or a mixed solvent thereof. Preferred is tetrahydrofuran.
  • reaction step 4 (In the above formula, X 3 represents a halogen atom, and A, X 1 , Y, R 1 , R 2 , Z, n, m, p, q have the same meaning as described above.)
  • the compound represented by the formula (1e) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (1d) with a halogenating agent.
  • halogenating agent used in this reaction examples include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, sulfuryl chloride, thionyl chloride, and the like.
  • Preferred are chlorine, bromine, iodine, sulfuryl chloride and the like.
  • the solvent used in this reaction is, for example, halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, or a mixed solvent thereof. Preferred is dichloromethane.
  • the starting material represented by the above formula (6) is a known compound and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc.
  • the production intermediate represented by the above formula (8) is obtained by converting the compound represented by the above formula (6) and the compound represented by the above formula (7) into a base as in the above reaction step 5-1. It can be produced by reacting in the presence.
  • Examples of the base used in the reaction step 5-1 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is triethylamine.
  • Examples of the solvent used in the reaction step 5-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and cycloheptane; water or a mixed solvent thereof. Preferred is dichloromethane.
  • the production intermediate represented by the above formula (9) comprises, as in the above reaction step 5-2, a compound represented by the above formula (8) obtained in the above reaction step 5-1, and chlorosulfonic acid. It can be produced by reacting. Further, the production intermediate represented by the above formula (9) is prepared by reacting the fuming sulfuric acid with the compound represented by the above formula (8) obtained in the above reaction step 5-1, and then in the presence of a base. It can be produced by reacting with diphosphorus pentoxide.
  • Examples of the base used in the reaction step 5-2 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is potassium carbonate.
  • the production intermediate represented by the above formula (10) includes a compound represented by the above formula (9) obtained by the above reaction step 5-2, a metal and an acid, as in the above reaction step 5-3. It can be produced by reduction using lithium aluminum hydride or red phosphorus, iodine and an acid.
  • Examples of the metal used in the reaction step 5-3 include zinc, tin, iron, and nickel. Zinc and tin are preferable.
  • Examples of the acid used in the reaction step 5-3 include hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.
  • the production intermediate represented by the above formula (11) is obtained by reacting the compound represented by the above formula (10) obtained by the above reaction step 5-3 with the acid or base as in the above reaction step 5-4. It can manufacture by hydrolyzing using.
  • Examples of the acid used in the reaction step 5-4 include hydrochloric acid, sulfuric acid, acetic acid and the like. Preferred are hydrochloric acid, acetic acid and the like.
  • Examples of the base used in the reaction step 5-4 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diisopropylethylamine, pyridine and the like.
  • Sodium hydroxide, potassium hydroxide and the like are preferable.
  • the compound represented by the formula (2b) according to the present invention includes, for example, a production intermediate represented by the formula (11) obtained by the reaction step 5 and a compound represented by the formula (12). , And in the presence or absence of Rongalite (Rongalite, trade name of BASF; sodium hydroxymethanesulfinate dihydrate). Moreover, it can also manufacture by making it react in presence of a catalyst as needed.
  • Rongalite trade name of BASF; sodium hydroxymethanesulfinate dihydrate
  • the raw material represented by the above formula (12) is known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.
  • the amount of the raw material represented by the formula (12) used here may be appropriately selected from the range of 1 to 5 mol with respect to 1 mol of the compound represented by the formula (11). 0 to 2.0 moles.
  • Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine, sodium hydroxide, potassium hydroxide and the like. It is. Preferred is potassium carbonate.
  • the amount of the base used here may be appropriately selected from the range of 0 to 5 mol, preferably 0 to 2.0 mol, per 1 mol of the compound represented by the formula (11).
  • Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide or a mixture of
  • the amount of the solvent used may be appropriately selected from the range of 0.1 to 100 liters with respect to 1 mol of the compound represented by the formula (11), and preferably 1.0 to 5.0 liters.
  • the reaction temperature may be selected from an arbitrary range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and preferably from 0 ° C. to 150 ° C.
  • the reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is preferably in the range of 10 minutes to 20 hours.
  • the compound represented by the formula (2c) according to the present invention can be produced, for example, by reacting the compound represented by the above formula (2b) with an oxidizing agent.
  • oxidizing agent used in this reaction examples include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI DuPont; trade name; peroxohydrogensulfate Potassium-containing substances), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like.
  • OXONE registered trademark, manufactured by EI DuPont; trade name; peroxohydrogensulfate Potassium-containing substances
  • N-chlorosuccinimide N-bromosuccinimide
  • tert-butyl dichlorite sodium hypochlorite
  • oxygen and the like Preferred are m-chloroperbenzoic acid and hydrogen peroxide.
  • the amount of the oxidizing agent used here may be appropriately selected from the range of 1.0 to 6.0 mol, preferably 1.0 to 2 with respect to 1 mol of the compound represented by the formula (2b). 0.0 mole.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; pentane and hexane Aliphatic hydrocarbons such as cyclohexane and cycloheptane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid, water, or a mixed solvent thereof.
  • ethers such as dieth
  • the amount of the solvent used may be appropriately selected from the range of 0.1 to 100 liters, preferably 1.0 to 5.0 liters, per 1 mol of the compound represented by the formula (2b).
  • the reaction temperature may be selected from an arbitrary range from ⁇ 30 ° C. to the reflux temperature in the reaction system, and preferably from ⁇ 10 ° C. to 50 ° C.
  • the reaction time varies depending on the reaction temperature, reaction substrate, reaction amount, etc., but is preferably in the range of 10 minutes to 20 hours.
  • the compound according to the present invention represented by the formula (1-6) can be produced according to the production methods shown below, but is not limited to these methods.
  • reaction step 8 (In the above formula, A 100 , X 101 , X 102 , Y 100 , R 101a , R 102a , R 101b , R 102b , W 1 , W 2 , v, u are represented by the above formula (1-6). The same meaning as the N-substituted aniline compound is shown, and n represents 1 or 2.)
  • the compound represented by the formula (1-6b) according to the present invention can be obtained, for example, by reacting the compound represented by the above formula (1-6a) with an oxidizing agent in the presence of a catalyst as necessary.
  • a catalyst as necessary.
  • the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI Dupont); ), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like.
  • Preferred are m-chloroperbenzoic acid and hydrogen peroxide.
  • Examples of the catalyst used in this reaction include molybdenum oxide, boric acid, tris (acetylacetone) iron, and the like. Preferred is molybdenum oxide.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; pentane and hexane Aliphatic hydrocarbons such as cyclohexane and cycloheptane; ketones such as
  • L 100 represents a leaving group such as a halogen atom, an alkylsulfonyloxy group, a haloalkylsulfonyloxy group, an arylsulfonyloxy group, etc., and represents A 100 , X 101 , X 102 , Y 100 , R 101a , R 102a. , R 101b , R 102b , W 1 , W 2 , v, and u have the same meaning as described above, and n represents an integer of 0 to 2.
  • the compound represented by the formula (1-6) according to the present invention includes, for example, a compound represented by the above formula (13) and a compound represented by the above formula (14) in the presence of a base as necessary. It can be produced by reacting in the presence of a catalyst.
  • the raw material represented by the above formula (14) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.
  • Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like.
  • Examples of the base include potassium carbonate, triethylamine, potassium hydroxide, sodium hydroxide and the like.
  • Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide, dichloromethane, or a mixture of water and an organic solvent is preferred.
  • reaction step 10 (In the above formula, A 100 , X 101 , X 102 , Y 100 , R 101a , R 102a , R 101b , R 102b , W 1 , W 2 , n, v, and u have the same meanings as described above).
  • the compound represented by formula (1-6) according to the present invention is, for example, Bulletin of the Chemical Society of Japan, 1967, p. 936, Bulletin of the Chemical Society of Japan, 1967, p. According to the method described in 2380, the compound represented by the above formula (13) and the compound represented by the above formula (15) can be produced by Mitsunobu reaction.
  • the raw material represented by the above formula (15) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.
  • Examples of the phosphorus compound used in this reaction include triphenylphosphine, tri-n-butylphosphine, tritert-butylphosphine, phenoxydiphenylphosphine, and the like. Preferred are triphenylphosphine and phenoxydiphenylphosphine.
  • Examples of the azodicarboxylic acid ester used in this reaction include diethyl azodicarboxylate and diisopropyl azodicarboxylate. Preferred is diethyl azodicarboxylate.
  • solvent used in this reaction examples include ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated carbonization such as dichloromethane, chloroform and 1,2-dichloroethane.
  • Hydrogens aliphatic hydrocarbons such as pentane, hexane, cyclohexane, cycloheptane or a mixed solvent thereof. Preferred is tetrahydrofuran.
  • reaction step 11 (In the above formula, X 103 represents a halogen atom, and A 100 , X 101 , Y 100 , R 101a , R 102a , R 101b , R 102b , W 1 , W 2 , n, v, and u have the same meaning as described above. Is shown.)
  • the compound represented by the formula (1-6d) according to the present invention is obtained by, for example, reacting the compound represented by the above formula (1-6c) with a halogenating agent in the presence of a catalyst as necessary.
  • a halogenating agent used in this reaction include chlorine, bromine, iodine, N-chlorosuccinimide, N-bromosuccinimide, N-iodosuccinimide, sulfuryl chloride, thionyl chloride and the like.
  • Preferred are chlorine, bromine, iodine, sulfuryl chloride and the like.
  • Examples of the catalyst used in this reaction include aluminum chloride and phenyl sulfide. Aluminum chloride is preferred.
  • the solvent used in this reaction include halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, acetic acid, and mixed solvents thereof. Preferred is dichloromethane.
  • PG 100 represents a protecting group such as an alkylcarbonyl group, a haloalkylcarbonyl group, an arylcarbonyl group, or an alkoxycarbonyl group, and X 101 , X 102 , and L 100 have the same meaning as described above.
  • the starting material represented by the above formula (16) is a known compound, and a commercially available product can be used.
  • the production intermediate represented by the above formula (18) is obtained by converting a compound represented by the above formula (16) and a compound represented by the above formula (17) into a base as in the above reaction step 12-1. It can be produced by reacting in the presence.
  • Examples of the base used in the reaction step 12-1 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropyl. Ethylamine, pyridine and the like. Sodium hydroxide, potassium hydroxide, triethylamine and the like are preferable.
  • Examples of the solvent used in the reaction step 12-1 include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; dichloromethane, chloroform, 1,2-dichloroethane, and the like. Halogenated hydrocarbons; aliphatic hydrocarbons such as pentane, hexane, cyclohexane and cycloheptane; water or a mixed solvent thereof. Preferred is dichloromethane or a mixture of water and an organic solvent.
  • the production intermediate represented by the above formula (19) comprises, as in the above reaction step 12-2, a compound represented by the above formula (18) obtained in the above reaction step 12-1 and chlorosulfonic acid. It can be produced by reacting.
  • the production intermediate represented by the above formula (19) is produced by reacting fuming sulfuric acid with the compound represented by the above formula (18) and then reacting with diphosphorus pentoxide in the presence of a base. can do.
  • Examples of the base used in the reaction step 12-2 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Preferred is potassium carbonate.
  • the production intermediate represented by the above formula (20) includes a compound represented by the above formula (19) obtained by the above reaction step 12-2, a metal and an acid, as in the above reaction step 12-3. It can be produced by reduction using lithium aluminum hydride or red phosphorus, iodine and an acid.
  • Examples of the metal used in the reaction step 12-3 include zinc, tin, iron, and nickel. Zinc and tin are preferable.
  • Examples of the acid used in the reaction step 12-3 include hydrochloric acid, sulfuric acid, and acetic acid. Preferred are hydrochloric acid, acetic acid and the like.
  • the production intermediate represented by the above formula (21) comprises a compound represented by the above formula (20) obtained by the above reaction step 12-3, an acid or a base, as in the above reaction step 12-4. It can manufacture by hydrolyzing using.
  • Examples of the acid used in the reaction step 12-4 include hydrochloric acid, sulfuric acid, acetic acid and the like. Preferred are hydrochloric acid, acetic acid and the like.
  • Examples of the base used in the reaction step 12-4 include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, triethylamine, diisopropylethylamine, pyridine and the like. Sodium hydroxide, potassium hydroxide and the like are preferable.
  • the compound represented by the above formula (23) is obtained by, for example, converting the production intermediate represented by the above formula (21) obtained by the reaction step 12 and the compound represented by the above formula (22) into a base. It can be produced by reacting in the presence and absence of Rongalite (Rongalite, manufactured by BASF; sodium hydroxymethanesulfinate dihydrate). Moreover, it can also manufacture by making it react in presence of a catalyst as needed.
  • Rongalite manufactured by BASF; sodium hydroxymethanesulfinate dihydrate
  • the raw material represented by the above formula (22) is known in some cases, and a commercially available product can be used. Or it can also manufacture easily from the reagent which can be obtained according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc.
  • Examples of the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine, sodium hydroxide, potassium hydroxide and the like. It is. Preferred is potassium carbonate.
  • Examples of the catalyst used in this reaction include tetrabutylammonium bromide or tetrabutylammonium chloride.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. N, N-dimethylformamide or a mixture of water and an organic solvent is preferred.
  • the compound represented by the above formula (24) can be produced, for example, by reacting the compound represented by the above formula (23) with an oxidant in the presence of a catalyst as necessary.
  • a catalyst as necessary.
  • the oxidizing agent used in this reaction include hydrogen peroxide, m-chloroperbenzoic acid, sodium periodate, OXONE (registered trademark, manufactured by EI Dupont); ), N-chlorosuccinimide, N-bromosuccinimide, tert-butyl dichlorite, sodium hypochlorite, oxygen and the like.
  • the catalyst used in this reaction include molybdenum oxide, boric acid, tris (acetylacetone) iron, and the like. Preferred is molybdenum oxide.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone and sulfolane; alcohols such as methanol, ethanol and isopropyl alcohol; halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane; pentane and hexane Aliphatic hydrocarbons such as cyclohexane and cycloheptane; ketones such as acetone, methyl ethyl ketone, and cyclohexanone; acetic acid, water, or a mixed solvent thereof.
  • ethers such as dieth
  • the compound represented by the formula (27) according to the present invention is, for example, Tetrahedron, 2011, p. According to the method described in 2323 and the like, it can be produced by Fenton reaction of the compound represented by the above formula (25).
  • the raw materials represented by the above formulas (25) and (26) are known in some cases and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.
  • the peroxide used in this reaction include hydrogen peroxide, hydrogen peroxide-urea complex, tert-butyl peroxide, and peracetic acid. Preferred is hydrogen peroxide.
  • the catalyst used in this reaction is, for example, iron (II) sulfate, iron (II) ammonium sulfate, iron (II) tetrafluoroborate, iron (II) chloride, iron (II) bromide, iron iodide (II). ), Iron (II) acetate, iron (II) oxalate, bis (acetylacetonato) iron (II), ferrocene, and the like. Preferred is ferrocene.
  • Examples of the solvent used in this reaction include aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof.
  • aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof.
  • Preferred is dimethyl sulfoxide.
  • the compound represented by the formula (28) according to the present invention is described in, for example, Chemical and Pharmaceutical Bulletin, 1999, p. According to the method described in 1013 and the like, the compound represented by the above formula (28) and the compound represented by the formula (26) can be produced by a coupling reaction in the presence of copper.
  • the raw material represented by the above formula (28) is known in some cases, and can be obtained from Tokyo Chemical Industry Co., Ltd., Sigma Aldrich Co., etc. Or it can also manufacture easily according to the well-known method as described in an experimental chemistry course, Organic Synthesis, etc. from an available reagent.
  • Examples of the solvent used in this reaction include aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof.
  • aprotic polar solvents such as dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, diisopropyl sulfoxide, diphenyl sulfoxide, and methylphenyl sulfoxide, or a mixed solvent thereof.
  • Preferred is dimethyl sulfoxide.
  • the compound represented by the formula (29) according to the present invention can be produced by reducing the compound represented by the above formula (27).
  • the reducing agent used in this reaction include sodium borohydride, lithium aluminum hydride, diisobutylaluminum hydride, and the like. Preferred is sodium borohydride.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; alcohols such as methanol, ethanol and isopropyl alcohol; dichloromethane and chloroform Halogenated hydrocarbons such as 1,2-dichloroethane; aliphatic hydrocarbons such as pentane, hexane, cyclohexane, and cycloheptane; water or a mixed solvent thereof.
  • ethers such as diethyl ether, tetrahydrofuran and dioxane
  • aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene
  • alcohols such as methanol, ethanol and isopropyl alcohol
  • dichloromethane and chloroform Halogenated hydrocarbons such as 1,2-
  • reaction step 18 (In the formula, R 104 'indicates which may C 1 ⁇ C 4 alkylsulfonyl group which may or C 1 ⁇ C 4 alkyl optionally substituted arylsulfonyl group, substituted with a halogen atom, Y 100, W 3 , W 4 , v, and L 100 have the same meaning as described above.)
  • the compound represented by the formula (31) according to the present invention is produced, for example, by reacting the compound represented by the above formula (29) and the compound represented by the above formula (30) in the presence of a base.
  • a base be able to.
  • the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like.
  • the base Preferred is triethylamine.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. Preferred is dichloromethane.
  • W 3 ′ and W 4 ′ are each independently substituted with a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxycarbonyl group, or a halogen atom, which may be substituted with a halogen atom.
  • a C 1 -C 6 alkylsulfonyl group which may be substituted, and Y 100 , v, G and L 100 have the same meaning as described above.
  • the compound represented by the formula (34) according to the present invention is produced, for example, by reacting the compound represented by the above formula (32) and the compound represented by the above formula (33) in the presence of a base. be able to.
  • the compound represented by the formula (36) according to the present invention is produced, for example, by reacting the compound represented by the above formula (34) and the compound represented by the above formula (35) in the presence of a base. can do.
  • the base used in this reaction include potassium carbonate, sodium carbonate, cesium carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, lithium hydride, sodium amide, triethylamine, diisopropylethylamine, pyridine and the like. Of the base.
  • Solvents used in this reaction include, for example, ethers such as diethyl ether, tetrahydrofuran and dioxane; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; acetonitrile, N, N-dimethylformamide, N, N-dimethyl Aprotic polar solvents such as acetamide, N-methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane; fats such as pentane, hexane, cyclohexane, cycloheptane Group hydrocarbons, water or a mixed solvent thereof. Preferred is dichloromethane.
  • the target compound can be obtained by performing ordinary operations in organic synthesis such as extraction, drying, concentration, and purification after completion of the reaction.
  • the structure of the target compound can be identified by a known analysis means such as an NMR spectrum.
  • the substituted phenyl ether compound according to the present invention is not limited to the above production method, and can be produced by any organic synthesis technique.
  • this invention compound can exhibit the outstanding control activity with respect to a wide range of insects, mites, crustaceans, molluscs, and nematodes.
  • the compound of the present invention exhibits excellent control activity especially against insects and mites.
  • the compound represented by the above formula (1-1) is preferable because it exhibits a very excellent control activity against mites.
  • the compound represented by the above formula (1-2) is particularly preferable because it has excellent residual effect to maintain the control activity against mites even after spraying.
  • the compound represented by the above formula (1-2) is excellent in safety from oral administration tests on mice. Specific examples of the organism in which the compound of the present invention exhibits a controlling activity include the following.
  • Grasshopper (Ruspolia lineosa), Enma cricket (Teleoglyllus emma), Kera (Gryllotalpa orientalis), Tonosama locust (Locusta migratoria), Kobaneigo (Ezoa) Chathamate (Trogium pulsatorium), Hiratachate (Liposcelis bostrychofila), Usgro chatter (Liposcelis corrodens), etc. Chrysanthemum chicks (Lipeurus caponis), chicks (Menacanthus stramineus), bull lice (Damalinia bovis), horse lice (Damalinia caprae), etc.
  • Louseed cattle lice (Haematopinus eurosternus), swine lice (Haematopinus suis), louse lice (Pediculus humanus capitis), head lice (Pediculus humus pus), thrips pi Thysanoptera of Hirazuhanaazamiuma (Frankliniella intonsa), western flower thrips (Frankliniella occidentalis), Croton thrips (Heliothrips haemorrhoidalis), soybean thrips (Mycterothrips glycines), yellow tea thrips (Scirtothrips dorsalis), rice thrips (Stenchaetothrips biformis), Minami thrips ( Thrips palmi, Thrips tabaci, Hemithrips aculatus, Phytothrips diospyros i) etc.
  • rottorus clavatus Coleus puntigger, Rhopalus mculatus, Chimex lectularis, etc.
  • Coleoptera of Aodougane (Anomala albopilosa), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), flower chafer (Eucetonia pilifera), core Oh flower chafer (Gametis jucunda), Nagachakogane (Heptophylla picea), Japanese beetle (Popillia japonica), Tobiiromuna Boletus (Agriotes ogurae fuscicollis), White-headed click (Ectinus sericeus sericeus), Marubitus forumni fortum (Tobacco) Banmushi (Lasioderma serricorne), red flour (Tenebroides mauritanicus), Hime Hirata Keshikisui (Epuraea domina),
  • White butterfly Pieris rapae crucivora
  • Ichimon seiseri Parnara gutata guttata
  • Artemisia dasak Ascotis selenaria
  • Chadokuga Arna pseudoconsperga
  • the United States white Arctiidae Hyphantria cunea
  • black cutworm Agrotis ipsilon
  • Kaburayaga Agrotis segetum
  • Tamanagin'uwaba Autographa nigrisigna
  • cotton bollworm Helicoverpa armigera
  • Heliothis Heliothis spp.
  • Miostra brassicae Mythimna separata, Naranga aenescens, Spodoptera exigua, Spodopter ur spo Hymenoptera of Chu range sawfly (Arge pagana), Kaburahabachi (Athalia rosae ruficornis), Kuritamabachi (Dryocosmus kuriphilus), Kiirosuzumebachi (Vespa simillima xanthoptera), Formica japonica (Formica japonica), Iehimeari (Monomorium pharaonis), fire ant (Solenopsis invicta), etc. Is mentioned.
  • Sheep 9,000 mites (Psoroptes ovis), cat foraminous mites (Notoedres cati), SENKOU mites (Sarcoptes scabiei), red mites (Leptotrombidium akamushi), Nekotsumedani (Cheyletiella blakei), Inutsumedani (Cheyletiella yasguri), farinae (Dermatophagoides farinae) , Latrodetectus hasseltii and the like.
  • Obidu depts As the crustaceans, the Obidu depts (Oxidus gracilis), etc. Isopods such as Armadillium vulgare, Ten-legged American crayfish (Procambarus clarkii), For example, Boletiella hortensis.
  • primordial string eyes such as Pomacea canalicula
  • Examples include pulmonary African mussel (Achatina falica), slug (Meghiatum bilineatum), chakoura slug (Lehmannina valentiana), and Usuka westmai (Acusta specta sieboldiana).
  • Nematodes include strawberry nematodes (Notothylenchus acris), sweet potato root nematodes (Meloidogyne incognita), potato cyst nematodes (Globodera rostemisen), soybean cyst nematodes (Heterocernes) Pratylenchus coffea, Pratylenchus penetran, Nepalese nematode (Pratylenchus yamagutii), Nepheline nematode (Aphelenchus avenae), Oxalic (Aphelenchoides besseyi), horn wood nematode (Bursaphelenchus xylophilus), and the like.
  • animal internal parasites include roundworms, worms, etc., filariae, liver dystomia, lung dystoma, Yokokawa flukes, Schistosoma japonicum, striped worms, striped worms, echinococcus Examples include headworms.
  • the compound of the present invention can be used as an active ingredient of agricultural and horticultural pest control agents.
  • suitable carriers, surfactants, fluidity improvers, bindings described in the Agricultural Chemicals Formulation Guide (edited by: Japanese Society for Agricultural Chemicals Application Methods, published by Japan Society for Plant Protection, 1997) You may mix
  • an auxiliary agent may be blended in the formulation.
  • the agricultural and horticultural pest control agent containing the compound of the present invention can be formulated into any dosage form generally used as a dosage form for agricultural and horticultural pest control agents.
  • powder, coarse powder, DL (driftless) powder, flow dust, fine granules, fine granules, granules, wettable powder, wettable powder, liquid, sol (flowable), emulsion, and oil it is not limited to these.
  • mineral carriers kaolin, bentonite, clay, montmorillonite, talc, vermiculite, gypsum, diatomaceous earth, white clay, calcium carbonate, white carbon, quartz sand, ammonium sulfate, urea, etc.), vegetable powder (crystalline cellulose, etc.) ), Polymer compounds (petroleum resin, etc.), alumina, silicates, sugar polymers and the like.
  • Liquid carriers include water, alcohols (methanol, ethanol, n-propanol, ethylene glycol, glycerin, etc.), ethers (diethyl ether, tetrahydrofuran, 1,4-dioxane, cellosolve, etc.), ketones (methyl ethyl ketone, Cyclohexanone, etc.), esters (ethyl acetate, butyl acetate, fatty acid glycerin ester, etc.), nitriles, sulfoxides (dimethyl sulfoxide, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or Alicyclic hydrocarbons (kerosene, kerosene, cyclohexane, etc.), aromatic hydrocarbons (benzene, toluene, xylene, solvent naphtha, methylnaphthalene, etc.),
  • a surfactant can be blended for the purposes of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading, spreading, and disintegration.
  • Such surfactants include nonionic surfactants (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene alkyl phenyl ethers, polyoxyethylene aryl phenyl ethers, polyoxyethylene sorbitan alkyl esters, sorbitans).
  • Alkyl esters polyoxyethylene alkylene glycols, polyoxyethylene-polyoxypropylene block polymers, etc.
  • anionic surfactants alkyl benzene sulfonates, alkyl naphthalene sulfonates, lignin sulfonates, alkyl sulfosuccinates, alkyls) Sulfate, polyoxyethylene alkyl sulfate, aryl sulfonate, polyoxyalkylene alkyl ether phosphate ester, polyoxy Siethylene alkyl ether phosphates, polycarboxylates, etc.), cationic surfactants (alkylamines such as laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, polyoxyethylene alkylamines, etc.) ), Amphoteric surfactants (dialkylaminoethyl betaine, alkyldimethylbenzyl be
  • examples of the fluidity improver include isopropyl phosphate ester and calcium stearate.
  • Binders include methylcellulose, carboxymethylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, starch, carboxymethyl starch, dextrin, pullulan, sodium alginate, mannan, pectin, tragacanth gum, mannitol, sorbitol, propylene glycol alginate, guar gum Locust bean gum, gum arabic, xanthan gum, gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, ethylene / propylene block polymer, sodium polyacrylate, polyvinyl pyrrolidone, calcium lignin sulfonate and the like.
  • thickeners examples include guar gum, xanthan gum, tragacanth gum, casein, dextrin, colloidal hydrous aluminum silicate, colloidal hydrous magnesium silicate, colloidal hydrous aluminum silicate, carboxymethylcellulose, polyvinyl alcohol and water-soluble cellulose ether. It can be illustrated.
  • preservatives include sodium benzoate, potassium sorbate, p-chloro-metaxylenol, butyl p-oxybenzoate and 1,2-benzisothiazolin-3-one.
  • the content of the compound of the present invention can be appropriately selected depending on the dosage form of the preparation and the method of use.
  • the preferable content is in the range of 0.0001 to 90% by weight based on the total amount of the preparation.
  • a powder in the case of a powder, it is usually 0.01 to 50% by weight, preferably 0.05 to 20% by weight, based on the total amount of the preparation. 0.01 to 90% by weight, preferably 0.1 to 60% by weight. In the case of an emulsion, it is usually 0.01 to 80% by weight, preferably 0.1 to 70% by weight based on the total amount of the preparation. If it is a flowable agent, it is usually 0.01 to 60% by weight, preferably 0.1 to 50% by weight, based on the total amount of the formulation. The range is usually 0.01 to 50% by weight, preferably 0.1 to 20% by weight.
  • a bactericidal agent a fungicide, a bactericidal agent, an antiviral agent, a plant resistance inducer
  • a bactericidal agent fungicide, a bactericidal agent, an antiviral agent, a plant resistance inducer
  • Fungicide (1) Copper agent: Basic copper chloride, basic sulfur copper, cupric hydroxide, copper sulfate, oxine-copper, nonylphenol sulfone Copper (copper nonylphenol sulfate), DBEDC, etc.
  • Inorganic fungicide Sulfur (sulfer), lime sulfur compound (sodium hydrogen carbonate), potassium hydrogen carbonate (potassium hydrogen carbonate), metallic silver (silver) and the like.
  • Benzimidazole fungicides Carbendazim, thiabendazole, thiophanate-methyl, benomyl and the like.
  • Dicarboximide fungicides iprodione, procymidone, vinclozolin and the like.
  • Carboxamide fungicides oxycarboxin, carboxin, mepronil, flutolanil, boscalid, fluopyram, furamethizmza Penthiopyrad, bixafen, penflufen, fluxapyroxad, isopyrazam, tolfenpyrad, sedaxane, etc.
  • Phenylamide fungicides Metalaxyl, metalaxyl-M, oxadixyl, furalaxyl, ofuras, benalaxyl, and nalaxyl.
  • SBI agents triflumizole, prochloraz, oxpoconazole fumarate, triadimefone, bittertanol, microbutanol, microbutanol , Hexaconazole, tebuconazole, propiconazole, prothioconazole, difenoconazole, iconconole and ibconazole.
  • Strobilurin fungicides azoxystrobin, cresoxime-methyl, trifloxystrobin, methinostrobin, orysastrobrobin, orysastrobrobin Enestroburin, dimoxystrobin, picoxystrobin, pyribencarb, fluoxastrobin and the like.
  • Phenylpyrrole fungicides such as fludioxonil and fenpiclonil.
  • BAF-1120 code number
  • MIF-1002 code number
  • SYJ-264 code number
  • NNF-0721 code number
  • Insecticide (1) Organophosphorus insecticides acephate, azinephos-methyl, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, diaphos, diphos (Diazinon), diclofenthion, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, ethiphos, etiophos, ethophos os), fenitrothion, fenthion, isofenphos, isoxathion, malathion, methidathion, mevinphos, monotophos, monotophos -Methyl (oxydemethon-methyl), parathion (parathion), parathion-methyl (parathion-methyl), phentoate, folate, phosalone, phosmetone, phosphamidone n), phoxim, pirimiphos-methyl, profenofos, propaphos, prothi
  • Nereistoxin insecticides such as bensultap, cartap hydrochloride, thiocyclam and the like.
  • Neonicotinoid insecticides acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiacloprid.
  • Diamide-based insecticides such as chlorantraniliprole, cyantraniliprole, and flubendamide.
  • Phenylpyrazole insecticides such as acetoprole, etiprole, fipronil, fluffiprole, pyrafluprole, pyriprole.
  • Macrolide insecticides abamectin, avermectin, avermectin benzoate, lepimectin, milbemectin, spinetoram, spinosadrum, spinosaramsp
  • Benzoylurea insecticides bistrifluron, chlorfluazuron, diflubenzuron, fluazuron, flucyclohexuron, flufenhexuron, flufenoxuron Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron and the like.
  • Diacylhydrazine insecticides such as chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like.
  • Triflumezopyrim Triflumezopyrim, AKD-1193 (code number), MIE-1209 (code number), NA-89 (code number), NC-515 (code number), ME5382 (code number), ZDI-2501 (code) Number) etc.
  • Acaricides acequinocyl, amidoflumet, amitraz, bifenazate, bromopropylate, clofentezine (clofente), clofentezine Cyhexatin, etoxazole, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrylim , Hexythiazox, propargite, piflubumide, pyrimidifene, pyridaben, spirodicifene, spiromethifen, spiromethifen .
  • NDV Nuclear polyhedrosis virus
  • GV granule disease virus
  • CPV cytoplasmic polyhedrovirus virus
  • EPV insect pox virus
  • Spore derived from Bacillus thuringiensis and produced crystal toxins and mixtures thereof, microorganisms used as insecticides and nematicides such as Steinerne carpocapsae and Pasteuria penetrans Pesticides, insect pheromone agents, insect attractants, etc.
  • the reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Table 13 shows 1 HNMR spectrum (CDCl 3 ) ⁇ (ppm) value, melting point (° C.) and the like of the synthesis example and the compound according to the present invention produced according to the synthesis example.
  • 1 HNMR data was measured with a JNM-ECS400 spectrometer (manufactured by JEOL Ltd.).
  • Table 14 shows the 1 HNMR spectrum (CDCl 3 ) ⁇ (ppm) value, melting point (° C.) and the like of the synthesis example and the compound according to the present invention produced according to the synthesis example.
  • 1 HNMR spectrum was measured with a JNM-ECS400 spectrometer (manufactured by JEOL Ltd.).
  • Reference Synthesis Example 1 to Reference Synthesis Example 21 show synthesis examples in which the starting materials of Synthesis Examples 1 to 38 are synthesized from commercially available products, but are not limited thereto.
  • Red phosphorus (16.99 g, 548.4 mmol) and iodine (1.99 g, 7.84 mmol) were added to an acetic acid solution (130 ml) of the obtained oily substance at room temperature, and the mixture was heated to reflux for 2 hours. Ice water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a brown oil (yield 30.13 g, yield 71%). The obtained oil was added to 10% aqueous potassium hydroxide solution (4 l) and heated to reflux for 3 hours. Concentrated hydrochloric acid was added to the reaction mixture to adjust to pH 7 and extracted with ethyl acetate.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Sodium hydride (60%, 2.19 g, 54.6 mmol) and methyl iodide (15.5 g, 110 mmol) were added to a dimethoxyethane solution (40 ml) of the obtained oil at 0 ° C., and the mixture was stirred at room temperature for 1 hour. Stir.
  • Red phosphorus (16.99 g, 548.4 mmol) and iodine (1.99 g, 7.84 mmol) were added to an acetic acid solution (130 ml) of the obtained oily substance at room temperature, and the mixture was heated to reflux for 2 hours. Ice water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a brown oil (yield 30.13 g, yield 71%). The obtained oil was added to 10% aqueous potassium hydroxide solution (4 l) and heated to reflux for 3 hours. Concentrated hydrochloric acid was added to the reaction mixture to adjust to pH 7 and extracted with ethyl acetate.
  • the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate.
  • the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • tert-butyl N-tert-butoxycarbonyl-N- (2,6-difluoro-4-formylphenyl) carbamate (4.17 g, 11.7 mmol) was added at 0 ° C. and reacted at room temperature for 1 hour.
  • the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure.
  • Formulation Examples 1 to 5 Specific examples of methods for formulating the compounds of the present invention as agricultural and horticultural insecticides and acaricides are shown in Formulation Examples 1 to 5.
  • Test Examples 1 to 7 Specific examples of the evaluation of the control effect using the pest control agent according to the present invention obtained as described above are shown in Test Examples 1 to 7.
  • Test Example 1 Control test against brown planthopper Rice seedlings cultivated in a plastic cup were placed on a turntable, and an emulsion diluted solution (500 ppm) prepared according to Formulation Example 3 was sprayed uniformly with a spray gun. After air-drying, it was placed in a polycarbonate plastic container with a nylon gorge on the lid, and 10 4th instar larvae were released, and placed in a constant temperature room at 25 ° C. Seven days after the release, the number of surviving insects was examined, and the death rate (%) was calculated by the following formula (a). The test was carried out in two consecutive systems.
  • the compounds of compound numbers 1-1, 1-2, 1-3, 1-106, 1-140, 1-245, and 2-7 showed a death rate of 80% or more.
  • the compound Nos. 1-1020, 2-3, 2-4, 2-727, 2-919, and 2-928 showed a death rate of 80% or more.
  • the compound No. 11-284 showed a death rate of 80% or more.
  • the compounds Nos. 1-629, 1-760, 2-166, 2-209, and 6-9 showed a control value of 80% or more.
  • the compounds Nos. 2-3, 2-728, 2-782, 2-794, 2-870, 2-919, 2-920, 2-995, and 2-1020 have a control value of 80% or more. It was.
  • the compounds Nos. 10-25, 10-62, 10-64, 11-69, 11-70, and 11-187 showed a control value of 80% or more.
  • the compound of ⁇ 511 showed a control value of 80% or more.
  • the compounds -360, 11-362, 11-388, and 11-444 showed a control value of 80% or more.
  • 1-147, 1-179, 1-214, 1-288, 1-403, 1-409, 1-708, 1-709, 1-921, 1-963, 2-82, 2 -93 indicates a control value of 80% or more and less than 90%, 1-56, 1-103, 1-216, 1-238, 1-438, 1-472, 1-508, 1-653, 1-721, 1-723, 1-737, 1-753, 1-768, 1-962, 2-363, 2-364, 2-432, 2-522, 2-700, 6-40 have a control value of 90% or more and 100 %, 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-17, 1-18, 1-47, 1-48, 1-53, 1 -54, 1-55, 1-57, 1-58, 1-61, 1-62, 1-73, 1-74, 1-89, 1-90, 1- 5, 1-96, 1-97, 1-99, 1-100, 1-102, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-1811- 119, 1-
  • 2-939 has a control value of 80% or more and less than 90%, and 1-1027, 2-850, 2-868, 2-885, 2-887, 2-889, 2-908, 2-921, 2-9271-1027, indicating a control value of 90% or more and less than 100%, 1-193, 1-194, 1-964, 1-965, 1-1016, 1-1017, 1-1020, 1-1021, 1-1024, 1-1026, 2-3, 2-4, 2-401, 2-402, 2-405, 2-406, 2-417, 2-439, 2-440, 2- 443, 2-444, 2-527, 2-528, 2-725, 2-726, 2-727, 2-728, 2-729, 2-730, 2-731, 2-732, 2-733, 2-734, 2-735, 2-736, 2-737, -738, 2-739, 2-740, 2-743, 2-744, 2-745, 2-746, 2-747, 2-748, 2-749, 2-750, 2-757, 2
  • 11-362 exhibits a control value of 80% or more and less than 90%
  • 11-64, 11-85, 11-174, 11-217, and 11-228 have a control value of 90% or more and less than 100%.
  • 11-383, 11-455, 11-496, 11-497, and 11-518 have a control value of 80% or more and less than 90%
  • 11-11, 11-20, 11-46, 11-137, 11-161, 11-170, 11-219, 11-452, 11-453, 11-494, 11-495, and 11-498 show control values of 90% or more and less than 100%, and 11-8 11-37, 11-49, 11-51, 11-52, 11-54, 11-55, 11-58, 11-59, 11-62, 11-92, 11-123, 11-124, 11 -126, 11-128, 11-131, 11-133, 11-144, 11-146, 11-147, 11-156, 11-158, 11-159, 11-162, 11-164, 11-176 , 1-182, 11-185, 11-189, 11-199, 11-214, 11-221, 11-272, 11-275, 11-298, 11-337, 11-344, 11-346, 11- 376, 11-392
  • Test Example 4 Control test 2 against spider mite Bean seedlings (second true leaf stage) cultivated in a plastic cup were placed on a turntable, and an emulsion diluted solution (5 ppm) prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed uniformly with a spray gun. After spraying, placed in a constant temperature room at 25 ° C. (16 hours illumination), and 7 days later, 10 adult female spider mite were released on leaf discs cut out from the first true leaf and allowed to stand in a constant temperature room at 25 ° C. . Two days after the release, the number of female adults was examined, and the death rate (%) was calculated by the following formula (d). The test was carried out in two consecutive systems.
  • Test Example 4 is an investigation of the residual effect of the compound of the present invention against the spider mite.
  • a 5 ppm emulsion diluent prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed on a bean seedling (second true leaf stage) and allowed to stand for 7 days. Thereafter, 10 spider mites were released on leaf discs prepared by cutting out the first true leaves, and the number of live spider mites surviving two days after the release was examined. The residual effect was investigated by spraying the drug and confirming the control effect after standing for 7 days.
  • Table 15 below shows the results of a control test 2 against the spider mite using the compounds in the present specification.
  • the compounds described in Reference Examples 1, 3, 5, 7, 13, 14, and 19 to 22 are the control values of 3.3 ppm emulsion diluent tested by the method according to Test Example 3 above. Since the control activity is further reduced 7 days after spraying, the control test 2 for the spider mite was not conducted.
  • Reference Example 4 using Compound No. 2-35 having a different molecular structure Reference Example 8 using Compound No. 2-266 having a molecular structure in which R 1a and R 2a are both methyl groups
  • the mortality was 27.8%, 8.2%, and 4.5%, respectively, which was lower than the mortality of 95.0% in Example 2 and inferior in residual efficacy.
  • the four compounds 2-209, 2-210, 2-447, and 2-448 exhibited very excellent mortality even after 7 days of spraying. It was confirmed that the difference in the structure caused a great difference in the residual effect. These four compounds maintained high control activity even after 7 days of spraying, and showed very excellent residual effect. In addition, these four compounds greatly reduced the number of nymph mite individuals radiated 7 days after spraying in only 2 days, and were also excellent in rapid action.
  • the pest control agent according to the present invention is useful as a pest control agent in any of the above pests.
  • the compound represented by the formula (1-2) is particularly useful as an acaricide because it has both residual effect and rapid effect.
  • Pesticide control test 3 Ten adult female spider mites were released on each green seedling cultivated in a plastic cup. One day after the release, the kidney seedlings were placed on a turntable, and an emulsion diluted solution (3.3 ppm) prepared according to Formulation Example 3 was sprayed uniformly with a spray gun. After spraying, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), and the number of female adults parasitized after 8 days of treatment was examined, and the control value (%) was calculated by the above formula (c). The test was carried out in two consecutive systems.
  • Test Example 5 is a control test for a spider mite that was performed at 500 ppm in Test Example 3 at a low concentration of 3.3 ppm. Table 16 below shows the results of the control test 3 against the spider mite using the compounds in the present specification.
  • the compound of 2-920 showed a control value of 90% or more.
  • the control values of the compounds Nos. 2-7, 2-8 and 2-727 were less than 60%.
  • Test Example 6 is an investigation of the residual effect of the compound of the present invention against the spider mite.
  • a 5 ppm emulsion diluent prepared by applying the compound of the present invention according to Formulation Example 3 was sprayed on a bean seedling (second true leaf stage) and allowed to stand for 7 days. Thereafter, 10 spider mites were released on leaf discs prepared by cutting out the first true leaves, and the number of live spider mites surviving two days after the release was examined.
  • the residual effect was investigated by spraying the drug and confirming the control effect after standing for 7 days. Table 17 below shows the results of the control test 4 against the spider mite using the compounds in the present specification.
  • the compounds of compound Nos. 2-912, 2-914, 2-916, and 2-920 have a very excellent mortality rate of 86.8% to 100% and are highly controlled even after 7 days of spraying. The activity was maintained and the residual effect was excellent.
  • the death rate of the 2-730 compound was 0-42.1%.
  • Control test 5 against spider mite A glass petri dish was filled with 0.3% undiluted agar, and 3 pieces of each 3 cm diameter bean leaf disk were placed. Ten adult female spider mites were released on each leaf disk. After the release, the emulsion diluted solution (1 ppm) prepared according to Formulation Example 3 was uniformly sprayed using an automatic spraying device (manufactured by Ikeda Rika). After spraying, it was placed in a constant temperature room at 25 ° C. (16 hours illumination), and the number of live insects was examined after 3 days, and the death rate (%) was calculated by the following formula (e). Table 18 below shows the results of the control test 5 against the spider mite using the compounds in the present specification.
  • the compounds Nos. 2-209, 2-210, 2-447, 2-448, and 2-920 showed a very excellent death rate of 84% to 100%.
  • the mortality of the compounds Nos. 2-35, 2-266, 2-557, and 2-727 was 0 to 37%.
  • the substituted phenyl ether compound according to the present invention has an excellent control effect against pests, the use of this as a pest control agent can effectively control pests.
  • the compound represented by the formula (1-2) has both a residual effect and a rapid effect on mites, and is useful as an active ingredient of an acaricide.
  • the N-substituted aniline compound according to the present invention has an excellent control effect against pests, the use of this as a pest control agent can effectively control pests.

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Abstract

La présente invention concerne : un nouveau composé phényl éther substitué qui a un effet de lutte contre les organismes nuisibles ; et un agent de lutte antiparasitaire qui contient ce composé phényl éther substitué comme principe actif. Un composé phényl éther substitué représenté par la formule (1) est utilisé comme solution.
PCT/JP2014/071593 2013-08-21 2014-08-18 Composé phényl éther substitué et agent de lutte antiparasitaire WO2015025826A1 (fr)

Applications Claiming Priority (8)

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JP2013-171608 2013-08-21
JP2013171608 2013-08-21
JP2013-264676 2013-12-20
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JP2014-036605 2014-02-27
JP2014036605 2014-02-27
JP2014-086297 2014-04-18
JP2014086297A JP2016185907A (ja) 2014-04-18 2014-04-18 Ｎ−置換アニリン化合物および有害生物防除剤

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016064990A (ja) * 2014-09-22 2016-04-28 国立大学法人山口大学 フルオロアルカン誘導体、ゲル化剤、液晶性化合物及びゲル状組成物
WO2018139560A1 (fr) 2017-01-26 2018-08-02 三井化学アグロ株式会社 Composé de pyridone et bactéricide à usage agricole et horticole utilisant celui-ci en tant que principe actif
WO2018190352A1 (fr) 2017-04-11 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
WO2018190350A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
WO2018190351A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
JP2018536019A (ja) * 2015-10-23 2018-12-06 シェンヤン・シノケム・アグロケミカルズ・アールアンドディー・カンパニーリミテッドＳｈｅｎｙａｎｇ Ｓｉｎｏｃｈｅｍ Ａｇｒｏｃｈｅｍｉｃａｌｓ Ｒ＆Ｄ Ｃｏ．， Ｌｔｄ． ビフェニル化合物及びその適用法
WO2018225829A1 (fr) 2017-06-08 2018-12-13 三井化学アグロ株式会社 Composé de pyridone et fongicide agricole et horticole
WO2019167814A1 (fr) 2018-02-27 2019-09-06 クミアイ化学工業株式会社 Procédé de production d'un composé mercapto-phénol et d'un intermédiaire dudit composé
WO2020022412A1 (fr) 2018-07-25 2020-01-30 三井化学アグロ株式会社 Composé de pyridone et fongicide agricole et horticole comprenant celui-ci en tant que constituant actif

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JPS6341451A (ja) * 1986-08-06 1988-02-22 Nippon Kayaku Co Ltd エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物
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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016064990A (ja) * 2014-09-22 2016-04-28 国立大学法人山口大学 フルオロアルカン誘導体、ゲル化剤、液晶性化合物及びゲル状組成物
JP2018536019A (ja) * 2015-10-23 2018-12-06 シェンヤン・シノケム・アグロケミカルズ・アールアンドディー・カンパニーリミテッドＳｈｅｎｙａｎｇ Ｓｉｎｏｃｈｅｍ Ａｇｒｏｃｈｅｍｉｃａｌｓ Ｒ＆Ｄ Ｃｏ．， Ｌｔｄ． ビフェニル化合物及びその適用法
WO2018139560A1 (fr) 2017-01-26 2018-08-02 三井化学アグロ株式会社 Composé de pyridone et bactéricide à usage agricole et horticole utilisant celui-ci en tant que principe actif
WO2018190350A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
WO2018190351A1 (fr) 2017-04-10 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
WO2018190352A1 (fr) 2017-04-11 2018-10-18 三井化学アグロ株式会社 Composé pyridone, et bactéricide à usage agricole et horticole ayant ce composé pour principe actif
WO2018225829A1 (fr) 2017-06-08 2018-12-13 三井化学アグロ株式会社 Composé de pyridone et fongicide agricole et horticole
WO2019167814A1 (fr) 2018-02-27 2019-09-06 クミアイ化学工業株式会社 Procédé de production d'un composé mercapto-phénol et d'un intermédiaire dudit composé
KR20200124227A (ko) * 2018-02-27 2020-11-02 구미아이 가가쿠 고교 가부시키가이샤 메르캅토페놀 화합물의 제조 방법 및 그 중간체
KR102279795B1 (ko) 2018-02-27 2021-07-21 구미아이 가가쿠 고교 가부시키가이샤 메르캅토페놀 화합물의 제조 방법 및 그 중간체
EP3760613A4 (fr) * 2018-02-27 2022-04-27 Kumiai Chemical Industry Co., Ltd. Procédé de production d'un composé mercapto-phénol et d'un intermédiaire dudit composé
CN114478336A (zh) * 2018-02-27 2022-05-13 组合化学工业株式会社 巯基酚化合物的制造方法及其中间体
CN114478336B (zh) * 2018-02-27 2024-05-14 组合化学工业株式会社 巯基酚化合物的制造方法及其中间体
WO2020022412A1 (fr) 2018-07-25 2020-01-30 三井化学アグロ株式会社 Composé de pyridone et fongicide agricole et horticole comprenant celui-ci en tant que constituant actif

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