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WO2000009481A1 - Composes d'amide cyclique, procedes de production correspondants, intermediaires correspondants et herbicides - Google Patents

Composes d'amide cyclique, procedes de production correspondants, intermediaires correspondants et herbicides Download PDF

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Publication number
WO2000009481A1
WO2000009481A1 PCT/JP1999/004327 JP9904327W WO0009481A1 WO 2000009481 A1 WO2000009481 A1 WO 2000009481A1 JP 9904327 W JP9904327 W JP 9904327W WO 0009481 A1 WO0009481 A1 WO 0009481A1
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Prior art keywords
group
carbonyl
alkyl
groups
halogen
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PCT/JP1999/004327
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English (en)
Japanese (ja)
Inventor
Takafumi Fusaka
Yasushi Tanaka
Atsushi Kadowaki
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Takeda Pharmaceutical Co Ltd
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Takeda Chemical Industries Ltd
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Priority to AU51959/99A priority Critical patent/AU5195999A/en
Publication of WO2000009481A1 publication Critical patent/WO2000009481A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings

Definitions

  • the present invention relates to a novel cyclic amide compound or a salt thereof exhibiting excellent selective herbicidal activity, a method for producing the same, a synthetic intermediate thereof, a herbicide containing the cyclic amide compound, and a water-floating particle containing the cyclic amide compound. Or aqueous suspensions.
  • the cyclic amide compound represented by the general formula (I) of the present invention has two substituents R 4 and Z at the position of the carbonyl group (that is, the position of the carbonyl group is a quaternary carbon). It has an excellent herbicidal action against various paddy field weeds and upland field weeds, and has no substantial phytotoxicity to cultivated crops such as rice, wheat, oats, soybean, corn, and wheat. It is used as an excellent selective herbicide in paddy fields and uplands.
  • the present inventors have conducted intensive studies with the aim of developing a selective herbicide having excellent herbicidal activity and having no phytotoxicity to crops.
  • the compound represented by the general formula (I) It is found that the salt has strong herbicidal activity, and also has a markedly reduced herbicidal effect on cultivated crops such as rice, wheat, oats, soybean, corn, and sorghum, and exhibits high selective herbicidal action. Furthermore, as a result of various studies based on these findings, the present invention has been completed.
  • R 1 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • R 5 and R 6 each represent a hydrogen atom, a hydrocarbon group which may be substituted, or a heterocyclic group which may be substituted.
  • R 2 and R 3 each represent a hydrogen atom or a hydrocarbon group which may be substituted, or R 2 and R 3 may be substituted with an adjacent carbon atom, and May form a cyclic hydrocarbon group,
  • R 4 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • W 1 represents an oxygen atom or an optionally oxidized sulfur atom
  • R 7 represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group.
  • A— is an expression — —
  • R 8 represents a hydrogen atom or an optionally substituted hydrocarbon group
  • R 9 represents a hydrogen atom, a cyano group, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group
  • R 15 represents a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group.
  • R 1G represents a hydrogen atom or an optionally substituted hydrocarbon group
  • R 11 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • W 2 represents an oxygen atom or an optionally oxidized sulfur atom
  • R 16 represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a substituted Represents an optionally substituted acyl group.
  • the carbon atom is bonded to the carbon atom to which Z is bonded.
  • Z is a halogen atom, a cyano group, a hydrocarbon group which may be substituted, an acyl group which may be substituted or a formula
  • R 53 and R 6a each represent a hydrogen atom or a hydrocarbon group which may be substituted.
  • compound (I) or a salt thereof
  • R 1 is [1] ⁇ - 6 alkyl group, C 3 6 cycloalkyl group, C 2 6 alkenyl group, C 3 6 cycloalkenyl group, C, 6 alkynyl group, C 6 14 Ariru group, C 7 _ j 9 Ararukiru group, C 8 - 20 ⁇ reel alkenyl groups and C 8 _ 2.
  • a hydrocarbon group selected from aryl alkynyl groups (when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is
  • alkyl-carbonylamino group 6 alkyl sulfonyl group Selected from the group consisting of a alkoxy group, an alkylthio group which may be substituted by 1 to 3 halogen atoms, a C 2 _ 6 alkenylthio group, a C 2 _ 6 alkynylthio group and a C 6 -i 4 arylthio group
  • a nitrogen atom (which may be oxidized) which may be substituted with 1 to 3 substituents or which may form a methylenedioxy group by joining two adjacent substituents together; an oxygen atom;
  • (10) a formyl group, an alkyl one carbonyl group, C 2 _ 6 alkenyl - carboxymethyl sulfonyl group, C 2 _ 6 alkynyl chromatography carbonyl group, C 3 _ 6 cycloalkyl - carbonylation le group, C 6 - 14 Ariru one carbonyl group , Ci-e alkoxy one carbonyl group, C 2 - 6 Arukeniruokishi one carbonyl group, C 2 - 6 Arukiniruokishi Ichiriki Ruponiru group, C 3 - 6 cycloalkyl O carboxymethyl one carbonyl group, C 6 _ 14 Ariruokishi one power Ruponiru group, C 7 - 19 Ararukiru Ichiriki Ruponiru group, 9 Ararukiruokishi - carbonyl group, 5-6-membered heterocyclic carbonyl group, condensed heterocyclic carbonyl and 5-6 member
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, In the case of a fused heterocyclic carbonyl group or a 5- to 6-membered heterocyclic acetyl group, substitute 1 to 3 with halogen
  • the Q G (a) which may be 1-5 amino substituted by halogen, respectively (i) an alkyl group, (ii) C 3 - 6 cycloalkyl group, (iii) C 2 - 6 an alkenyl group, (iv) C 3 _ 6 cycloalkenyl group, (v) C 2 - 6 alkynyl group, (vi) C 6 - 14 Ariru group, (vii) C 7 _ 19 Ararukiru group, ( viii) C 8 _ 20 Ariruarukeni Le group and (ix) C 8 - 2.
  • Ararukiru - carbonyl group, C 7 19 Ararukiruokishi Ichiriki Ruponiru groups, 5-6 membered heterocyclic carbonyl group, is Ashiru group (said Ashiru group selected from fused heterocyclic carbonyl groups and 5-6 membered heterocyclic ⁇ Se ethyl group
  • an alkyl carbonyl group an alkenyl carbonyl group, an alkynyl carbonyl group, an alkoxy carbonyl group, an alkenyl carbonyl group or an alkynyl oxy carbonyl group, hydroxy, cyano, sulfamoyl, mercapto, carboxy, 6- alkylthio group, halogen atom , ( ⁇ alkoxy group, a nitro group, 6 alkoxy - force Ruponiru group, amino, mono- or di ( ⁇ _ 6 alkylamino group, 0 ⁇ _ 6 alkoxy imino 1 in groups and
  • Q 1 is (a) hydrogen atom, (b) which may be 1-5 amino substituted with halogen, respectively (1) Jii 6 alkyl group, (ii) C 3 - 6 cycloalkyl group, ( iii) C 2 - 6 alkenyl group, (iv) C 3 - 6 cycloalkenyl group, (v) C 2 - 6 alkynyl group, Ji 4 Ariru group, (vii) C 7 _] 9 Ararukiru group, (viii) C 8 _ 20 ⁇ reel alkenyl groups and (ix) C 8 _ 2.
  • the acyl group is a cycloalkylcarbonyl group, an arylcarboyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, for fused heterocyclic carbonyl group or a 5-6 membered heterocyclic Asechiru group, a halogen at one to three substituted Ji may E alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl group, C 3 _ 6 cycloalkenyl groups, C 2 _ 6 alkynyl group, 1-3 optionally substituted alkoxy group with a halogen, a formyl group, 6 ⁇ Ruki Lou carbonyl groups, C 2 - 6 alkenyl chromatography carbonyl groups, C 2 _ 6 alkynyl monocarbonyl group
  • Q 2 is (a), respectively which may be 1-5 amino substituted with eight androgenic (i) C - 6 alkyl group, (ii) C 3 - 6 cycloalkyl group, (iii) C 2 _ 6 Alkene Le group, (iv) (: 3 _ 6 cycloalkenyl group, (V) C 2 - 6 alkynyl group, (vi) C 6 - 14 Ariru group, (vii) C 7 - 19 Ararukiru group, (viii) C 8 — 20 arylalkenyl groups and (ix) C 8 _ 2, hydrocarbon groups selected from aryl alkynyl groups or (b) formyl groups, alkyl monocarbonyl groups, C 2 _ 6 alkenylcarbonyl groups, C 2 _ 6 alkynyl chromatography carbonyl group, C 3 _ 6 cycloalkyl - carbonyl group, C 6 - 14 Ariru - carbonyl group, C
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, If the slip heterocyclic carbonyl group or a 5-6 membered heterocyclic Asechiru group, a halogen at one to three optionally substituted flicking 6 alkyl groups, C 3 - 6 cycloalkyl groups, C 2 - 6 alkenyl groups, C 3 - 6 cycloalkenyl group, C 2 _ 6 alkynyl group, 1-3 optionally substituted alkoxy group with a halogen, formyl, C ⁇ - 6 ⁇ Ruki Lou carbonyl group, C 2 - 6 alkenyl - carbonyl group , C 2 - 6 alkynyl one
  • ⁇ reel hydrocarbon group selected from alkynyl group, (b) C androgenic in 1-3 amino optionally substituted C alkyl group, C 3 _ 6 a cycloalkyl group, C 2 - 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 _ 6 alkynyl group, Ji 6 _ 14 Ariru group, C 7 _ 19 Ararukiru group, halogen 1-3 substituted Ji may alkoxy groups, C 2 - 6 Arukeniruokishi group, C 2 - 6 Arukiniruo alkoxy group, C 6 - 14 Ariruokishi group, C 7 _ 19 Ararukiruokishi group, a formyl group, an alkyl - Karuponiru group, C 2 - 6 Aruke alkenyl - carbonyl group, C 2 - 6 Al yn Lou carbonyl group , C 3 _ 6 cycloalkyl -
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, If the slip heterocyclic force Ruponiru group or 5-6-membered heterocyclic Asechiru group, a halogen at one to three substituted 6 may be alkyl groups, C 3 _ 6 cycloalkyl groups, C 2 - 6 alkenyl groups, C 3 6 cycloalkenyl groups, C 2 6 alkynyl group, 1-3 optionally substituted 6 alkoxy group by halogen, formyl, 6 ⁇ alkyl - carbonitrile alkenyl groups, C 2 _ 6 alkenyl chromatography carbonyl groups, C 2 _ 6 alkynyl carbonyl groups,
  • a 38-membered heterocyclic group containing 1 to 4 heteroatoms selected from an oxygen atom and a sulfur atom (which may be mono- or di-oxidized), or the 38-membered heterocyclic group and benzene A 3- or 8-membered compound containing 1 to 4 hetero atoms selected from a ring or nitrogen atom (which may be oxidized), an oxygen atom and a sulfur atom (which may be mono- or di-oxidized)
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- or 6-membered heterocyclic carbonyl group, In the case of a heterocyclic carbonyl group or a 56-membered heterocyclic acetyl group, 1
  • CI_ 6 alkyl group C 3 - 6 cycloalkyl group, C 2 - 6 alkenyl group, C 3 - 6 cycloalkenyl group, C 2 - 6 alkynyl groups, substituted one to three halogen which may be C alkoxy group, a formyl group, flicking 6 ⁇ Ruki Lou carbonyl group, C 2 - 6 alkenyl - carbonyl group, C 2 - 6 alkynyl Ichiriki Ruponiru group.
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, If the slip heterocyclic carbonyl group or a 5-6 membered heterocyclic Asechiru group, a halogen at one to three optionally substituted alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 - 6 cycloalkenyl group, C 2 - 6 alkynyl group, 1-3 optionally substituted C alkoxy group by halogen, formyl, ⁇ Ruki Lou carbonyl group, C 2 _ 6 alkenyl - carbonyl group, C 2 - e alkynyl - carbonyl groups, C 3 - 6
  • substituent group (A) may be substituted with 1-4 substituents Ru is selected from.
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is a substituent selected from the above-mentioned substituent group (A).
  • [2] 1-3 optionally substituted alkyl group with halogen, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkenyl group, C 2 _ 6 Arukini group, ⁇ 6 _ 14 Ariru group, C 7 _ 19 Ararukiru group may be 1-3 substituted by halogen - 6 alkoxy groups, C 2 - 6 Arukeniruokishi groups, C 2 - 6 Arukini Ruokishi group, Ji 6 _ 14 Ariruokishi group, C 7 - 19 Ararukiruokishi group, a formyl group, an alkyl one carbonyl group, C 2 _ 6 alkenyl chromatography carbonyl group, C 2 _ 6 alkynyl chromatography carbonyl group, Ji 3 _ 6 cycloalkyl - carbonyl group, C 6 _ 14 ⁇ Li - Lou carbonyl group, C ⁇
  • R 5 and R 6 each (1) a hydrogen atom, ( « ⁇ alkyl, C 3 _ 6 consequent opening alkyl group, C 2 6 alkenyl group, C 3 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 _ 14 7 aryl group, C 7 19 Ararukiru group, C s 20 ⁇ reel alkenyl groups and C 8 2 ⁇ ) hydrocarbon group
  • the hydrocarbon group is an alkyl group selected from ⁇ reel alkynyl group, an alkenyl group
  • the hydrocarbon group may be substituted with 1 to 4 substituents selected from the above-mentioned substituent group (A), wherein the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group,
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group
  • Flip 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 6 cycloalkyl alkenyl, c 2 - 6 alkynyl group, c 6 - 14 Ariru groups and c 7 - 19 selected from Araruki Le group 1 to 5 substituents may be substituted, and two adjacent substituents may be combined to form a methylenedioxy group.
  • 1-3-substituted 6 may be an alkyl group with halogen, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 - 14 Ariru group, C 7 19 Ararukiru groups, one to three optionally substituted C Bok 6 alkoxy group halogen, C 2 _ 6 Arukeniruokishi group, C 2 6 Arukiniruokishi group, C 6 14 Ariruokishi group, C 7 _ 19 Ararukiruokishi group, a formyl group, ⁇ I 6 ⁇ Ruki Lou carbonyl group, C 2 6 alkenyl - carbonyl group, C 2 _ 6 Arukiniru carbonyl group, c 3 _ 6 cycloalkyl - carbonyl group, c 6 - 14 Ariru - carboxymethyl group, ⁇
  • R 2 and R 3 are each a hydrogen atom or an alkyl group; 3 _ 6 cycloalkyl group, C 2 - 6 alkenyl group, (: 3 _ 6 cycloalkenyl group, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 _ 19 Ararukiru group, C 3 - 20 7 Reel alkenyl, and C 8 - 2Q hydrocarbon group (the hydrocarbon group is an alkyl group selected from ⁇ reel alkynyl group, in the case of alkenyl or alkynyl group, the hydrocarbon group is selected above-mentioned substituent group (a) power When the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkyl group or an arylalkyl group, the hydrocarbon group may be substituted with 1 to 4.
  • substituent group (A) which may be 1-5 amino substituted by halogen C DOO 6 alkyl group, C 3 _ Nkuroarukiru group, C 2 _ 6 alkenyl, C 3 - 6 Shikuroaruke Le group, C 2 - 6 alkynyl group, C 6 - 14 Ariru groups and C 7 - 19 Ararukiru may be 1-5 amino substituted by which Ru substituents selected from group together two substituents adjacent Or R 2 and R 3 may be substituted with 1 to 3 halogen atoms together with an adjacent carbon atom to form a C j — 6 alkyl group, C 3 - 6 cycloalkyl group, C 2 - 6 alkenyl group, C 3 - 6 Shikuroa alkenyl group, C 2 _ 6 alkynyl, C 6 - 14 Ariru group, C 7 _ 19 7 aralkyl group, 1 halogen to three optionally substituted alkoxy group, C 2 j — 6 al
  • aralkyloxy carbonyl group which may be 1-3 substituted with halogen ( ⁇ alkylsulfanyl Fier groups, C ⁇ - 6 ⁇ Luque Nils sulfinyl groups, C 2 _ 6 alkynylsulfinyl Group, C 6 14 ⁇ reel sulfinyl group, but it may also optionally be 1-3 substituted by halogen (6 alkylsulfonyl group, C 2 6 ⁇ Luque sulfonyl sulfonyl group, C 2 6 alkyl Nirusuruhoniru group, C 6 14 Arylsulfonyl, nitro, amino, mono- or dialkylamino, hydroxy, cyano, sulfamoyl, mercapto, halogen, formamide, 6- alkyl-carbonylamino, 6- alkylsulfonyl Okishi group, halogen 1-3 amino optionally substituted by Ji 6 alkyl,
  • R 4 is (C 6 alkyl group, Ji 3 _ 6 cycloalkyl group, C 2 6 alkenyl group, C 3 - 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 14 Ariru group, C 7 _ 19 ⁇ La alkyl group, C 8 _ 2.
  • the hydrocarbon group is an alkyl group selected in the case of alkenyl or alkynyl group, the hydrocarbon The group may be substituted with 1 to 4 substituents selected from the substituent group (A), wherein the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an aryl group.
  • halogen may be one to three substituents Ji Interview _ 6 alkyl le group, C 3 _ 6 cycloalkyl group , C 2 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 _ 6 alkynyl, C 6 14 Ariru group, C 7 19 Ararukiru group, an optionally C i 6 alkoxy which may be 1-3 amino substituted by halogen groups, C 2 6 Arukeniruokishi groups, C 2 _ 6 Arukiniruokishi groups, C 6 14 Ariruokishi groups, C 7 19 Ararukiru Okishi group, a formyl group, 6 alkylcarbonyl groups, C single _ 6 Aruke two Lou force Ruponiru groups, C 2 _ 6 alkynyl chromatography carbonyl groups, C 3 - 6 cycloalkyl
  • W 1 is an oxygen atom or a mono- or Jiokishido of which do also good sulfur atom
  • R 7 is (C - 6 alkyl groups, C 3 - 6 cycloalkyl groups, C 2 - 6 alkenyl le groups, C 3 - 6 cycloalkenyl group, C 2 _ 6 alkynyl, C 6 _ 14 Ariru group, C 7 - to 20 ⁇ reel alkenyl groups and C 8 _ 2 0 ⁇ Li one Ruaruki cycloalkenyl group - i 9 Ararukiru group, C 8 A selected hydrocarbon group (when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is selected from the group consisting of 1 to It may be substituted with four substituents.
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is a substituent selected from the above-mentioned substituent group (A), in 1-5 optionally substituted alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl group, 3 _ 6 cycloalkenyl group, C 2 - 6 Arukini le group, C 6 _ j 4 Ariru it may be 1-5 amino substituted with a substituent selected from the group and C 7 _ i 9 Ararukiru group, two adjacent substituents may form together a connexion Mechirenjio alkoxy group.
  • halogen 1-3 amino optionally substituted with not good 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 - 6 consequent Roarukeniru groups, C 2 - 6 alkynyl group, C 6 _ 14 Ariru group, C 7 _ 19 7 aralkyl group may be 1-3 substituted with halogen.
  • R 8 is a hydrogen atom or an alkyl groups, C 3 _ 6 cycloalkyl groups, C
  • hydrocarbon groups selected from aryl alkynyl groups (when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is selected from the above substituent groups
  • hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is a substituent selected from the above-mentioned substituent group (A); 1 to 5 may be substituted.
  • Preparative 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 shea Kuroarukeniru groups, C 2 - 6 alkynyl group, C 6 - 14 Ariru groups and C 7 - 19 ⁇ aralkyl group May be substituted with 1 to 5 substituents selected from the following, and two adjacent substituents may be taken together to form a methylenedioxy group.
  • R 9 is (1) hydrogen atom, (2) Shiano group, (3) ⁇ 6 alkyl group, ⁇ 3 _ 6 cycloalkyl Le group, C 2 - 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 - 19 Ararukiru group, C 8 _ 20 ⁇ reel alkenyl groups and C 8 - 2.
  • a hydrocarbon group selected from aryl alkynyl groups when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is It may be substituted with 1 to 4 substituents selected from the substituent group (A).
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is a substituent selected from the above-mentioned substituent group (A).
  • halogen 1-5 amino substituted Ji may alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 one 6 cycloalkenyl group, C 2 - 6 alkynyl group, ⁇ 6 may be substituted 1-5 atoms with a substituent selected from _ 14 Ariru groups and C 7 _ 19 Ararukiru group, two adjacent substituents may form together a connexion Mechirenjiokishi group.
  • halogen 1-3 amino optionally substituted alkyl group C 3 - 6 Shikuroa alkyl group, C 2 _ 6 alkenyl, C 3 - 6 cycloalkenyl group, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 - 19 Ararukiru groups, one to three optionally substituted alkoxy group with halogen, C 2 - 6 Arukeniruokishi group, C 2 _ 6 Arukini Ruokishi group, C 6 - 14 Ariruokishi group, C 7 - 19 Ararukiruokishi group, formyl group, an alkyl - carbonyl group, C 2 _ 6 alkenylene Luca Lupo alkenyl group, C 2 _ 6 alkynylene Luca Lupo alkenyl group, C 3 - 6 cycloalkyl - Karuponiru group, C 6 - 14 Ariru - Kar
  • 6 _ 14 Li one Rusurufiniru group, which may be 1-3 substituted by halogen C - 6 Al alkylsulfonyl group, C 2 - 6 alkenyl-sulfonyl group, C 2 - 6 Arukinirusuruho alkenyl group, C 6 - 14 arylsulfonyl, nitro, amino, mono- or dialkylamino, hydroxy, cyano, sulfamoyl, mercapto, halogen, formamide, alkyl-carbonylamino, alkylsulfonyloxy, halogen 1-3 amino optionally substituted alkylthio group, C 2 _ 6 alkenylthio group, C 2 _ 6 alkynyl Chio groups and C 6 _ i 4 1-3 selected from the group consisting ⁇ Li one thio group Replacements A nitrogen atom (which may be oxidized), an oxygen atom and a sulfur atom (which may be mono
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, for fused heterocyclic carbonyl group or a 5-6 membered heterocyclic Asechiru group, which may be 1-3 amino substitution with a halogen ( ⁇ alkyl, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl group , C 3 - 6 cycloalkenyl group, C 2 - 6 alkynyl group may be 1-3 substituted by halogen ⁇ - e alkoxy group, a formyl group, 6 alkyl - Cal JP99 / 04327
  • R 15 is (i) hydrogen atom, (IDci 6 alkyl group, Ji 3 _ 6 cycloalkyl groups, C 2 _ 6 alkenyl groups, C 3 _ 6 cycloalkenyl groups, C 2 _ 6 alkynyl groups, C 6 _ 14 Ariru group, C 7 19 Ararukiru group, C 8 _ 2.
  • the hydrocarbon group is an alkyl group selected from the group, ⁇ alkenyl group or an alkynyl
  • the hydrocarbon group may be substituted with 1 to 4 substituents selected from the above-mentioned substituent group (A), wherein the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group.
  • the hydrocarbon group is a substituent selected from the above-mentioned substituent group (A), and a C alkyl group which may be substituted with 1 to 5 halogen atoms.
  • C 3 _ 6 cycloalkyl group C 2 _ 6 alkenyl, C 3 6 cycloalkenyl group, C 2 - 6 alkynyl group, and 1 to have five substituted with location substituent selected from C 6 _ i 4 Ariru groups and C 7 _ 19 Ararukiru group And two adjacent substituents may be taken together to form a methylenedioxy group.) Or (iii) a C ⁇ —e alkyl group which may be substituted by 1 to 3 halogen atoms; 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl Le group, C 3 _ 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 _ 14 7 aryl group, C 7 - 19 Ararukiru group, three 1 halogen optionally substituted 6 alkoxy group, C 2 _ 6 Arukeniruokishi group, C 2 _ 6 Arukiniruok
  • R 1D is a hydrogen atom or Preparative 6 alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 an alkenyl group, C 3 - 6 cycloalkenyl group, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 - 19 Ararukiru group, C 8 - 20 ⁇ reel alkenyl group and a C 8 - 2.
  • a hydrocarbon group selected from an arylalkynyl group (when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group may be a substituted or unsubstituted 1 to 4 substituent group selected from the above substituent group (A))
  • the hydrocarbon group may be a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkyl group or an aryl group;
  • the hydrocarbon group above location substituent selected from Substituent Group (A) 1 to 5 amino optionally substituted alkyl group with halogen, C 3 6 consequent opening alkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkenyl group, a C 2 c alkynyl group, 1-have five substituted with a substituent selected from C 6 i 4 ⁇ Li Ichiru groups and C 7
  • R 11 is (1) hydrogen atom, (2) a halogen atom, (3) ⁇ 6 alkyl group, C 3 6 a cycloalkyl group, C 2 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 14 Ariru group, C 7 19 Ararukiru group, C 8 20 ⁇ reel alkenyl groups and C 8 2.
  • a hydrocarbon group selected from aryl alkynyl groups (in the case where the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is selected from the above-mentioned substituent group (A);
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an aryl alkenyl group or an arylalkynyl group
  • the hydrocarbon group is the above-mentioned substituent group (A ) power et substituents selected, halogen 1-5 amino optionally substituted ⁇ alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 Shikuroaruke alkenyl group, C 2 _ 6 alkynyl, C 6 14 Ariru groups and C 7 19 Ararukiru with a group or al selected substituents 1 may have
  • alkylsulfonyl O alkoxy group halogen 1-3 amino optionally substituted by C ⁇ 6 alkylthio group, C 2 - 6 alkenylthio group, C 2 - 6 alkynylthio groups and C 6 4 ⁇ Li
  • a nitrogen atom which may be substituted with 1 to 3 substituents selected from the group consisting of, or two adjacent substituents may together form a methylenedioxy group;
  • R 16 is (i) hydrogen atom, (i C ⁇ e; alkyl group, 3 _ 6 cycloalkyl groups, C 2 - 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 _ 19 Ararukiru group, C 8 - 20 ⁇ reel alkenyl groups and (8 _ 2.
  • a hydrocarbon group selected from aryl alkynyl groups (in the case where the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is selected from the above-mentioned substituent group (A);
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group, the hydrocarbon group is substituted as described above.
  • Substitution selected from group (A) Halogen 1-5 amino optionally substituted alkyl group, C 3 - 6 cycloalkyl group, C, _ 6 alkenyl, C 3 - 6 Cycloalkenyl group, c 2 - 6 alkynyl group, c 6 - 14 Ariru groups and c 7 one 1 9 Ararukiru may be 1-5 amino substituted with a substituent selected from the group, together two substituents adjacent May form a methylenedioxy group.
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- or 6-membered heterocyclic carbonyl group, If heterocyclic carbonyl group or a 5 6 membered heterocyclic Asechiru group, halogen 1 three replacement which may be optionally Bok 6 alkyl group, C 3 - 6 cycloalkyl group, C 2 _ 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 - 6 alkynyl group may be one to three substituted with halogen ⁇ - e alkoxy group, a formyl group, (: I 6 alkyl one local Boniru group, C 2 _ 6 alkenyl over carbonyl group, C 2 _ 6 alkynyl
  • Ariruokishi - carbonyl group, C 7 - 19 Ararukiru - Karuponiru Group, C 7 to 19 may be substituted with 1 to 5 substituents selected from carbonyl, nitro, amino, hydroxy, cyano, sulfamoyl, mercapto, halogen and alkylthio groups. ).
  • R 12 is a hydrogen atom, a halogen atom or an alkyl group, C 3 _ 6 cycloalkyl group, C 2 6 alkenyl group, C 3 _ 6 cycloalkenyl group, C 2 6 alkynyl group, C 6 - 14 ⁇ Li Ichiru group, C 7 _ 19 Ararukiru group, C 8 _ 20 ⁇ reel alkenyl groups and C 8
  • a hydrocarbon group selected from aryl alkynyl groups (in the case where the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is one to four substituents selected from the above substituent group (A)
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is the above-mentioned substituent group (A) substituents selected from, optionally 1 to 5 atoms optionally substituted with halogen C DOO 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkenyl group, C 2 _ 6 alkynyl, C 6 14 Ariru groups and C 7 19 Ararukiru may be 1-5 amino substituted by
  • Z is (1) halogen atom, (2) Shiano group, (3) 0 ⁇ 6 alkyl group, C 3 _ 6 Shikuroa alkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkenyl group, C 2 _ 6 alkynyl groups, C 6 _ 14 7 aryl group, C 7 _ 19 Ararukiru group, C 8 _ 20 ⁇ reel alkenyl groups and C 8 2.
  • a hydrocarbon group selected from aryl alkynyl groups (when the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group, the hydrocarbon group is selected from the above-mentioned substituent group (A);
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an arylalkenyl group or an arylalkynyl group
  • the hydrocarbon group is the above substituent A substituent selected from group (A), which is substituted with 1 to 5 halogens
  • group (A) which is substituted with 1 to 5 halogens
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group; Group, condensed heterocyclic carbonyl group or 5- to 6-membered acetyl group, 1 to 3 of which may be replaced by halogen — 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 — 6 alk alkenyl group, C 3 one 6 cycloalkenyl group, C 2 - 6 alkynyl group, 1-3 optionally substituted alkoxy group with a halogen, a formyl group, (: I 6 alkyl one local Boniru group, C 2 _ 6 .
  • alkenylcarbonyl chromatography carbonyl group C 2 - 6 alkynyl chromatography carbonyl group, C 3 _ 6 cycloalkyl - carbonyl group, C 6 - 14 Ariru one carbonyl group, (: alkoxy one carbonitrile Alkenyl group, C, _ R Arukeniruokishi one carbonyl group, 6 ⁇ Ruki cycloalkenyl O Kishi carbonyl group, C 3 - 6 cycloalkyl O carboxymethyl - carbonyl group,
  • each of R 5a and R 6a hydrogen atom or an alkyl groups, C 3 _ 6 consequent opening alkyl groups, C 2 - beta alkenyl groups, C 3 - 6 cycloalkenyl groups, C 2 - 6 alkynyl groups, C 6 to 14 aryl groups, C 7 to 19 aralkyl groups, C 8 to 20 aryl alkenyl groups and C 8 to 2.
  • hydrocarbon groups selected from aryl alkynyl groups, wherein the hydrocarbon groups are alkyl, alkenyl or alkynyl
  • the hydrocarbon group may be substituted with 1 to 4 substituents selected from the above-mentioned substituent group (A), wherein the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group.
  • an aralkyl group, an arylalkenyl group or an arylalkynyl group, the hydrocarbon group may be substituted with 1 to 5 substituents selected from the substituent group (A), a substituent selected from the above, Alkyl group, C 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 3 _ 6 cycloalkyl alkenyl, C 2 _ 6 alkynyl, C 6 - 14 Ariru groups and C 7 - 19 substituent selected from Araruki Le group 1
  • the compound according to the above [1] which may be substituted with up to 5 substituents and two adjacent substituents may be taken together to form a methylenedioxy group. Or its salt,
  • R 1 is the formula
  • X 1 is a halogen atom
  • X 1 is a halogen atom
  • X 1 may be 1-3 amino substituted by halogen same or different - 6 alkyl group, C 2 6 alkenyl, C 2 6 alkynyl group from 1 to 3 in Ha androgenic optionally substituted C l _ 6 alkoxy, C 2 _ 6 alkenyl Okishi group, C 2 6 Arukiniruokishi group, halogen 1-3 amino optionally substituted have good C ⁇ 6 alkylthio group, C 2 _ 6 alkenylthio group, C 26 alkynylthio group, 1 to 3 halogens may be substituted ( ⁇ _ 6 alkylsulfinyl group, C 2 _ 6 alkenylsulfinyl group, C 26 alkynylsulfinyl group, 1 to 3 halogen atoms may be substituted — 6 alkylsulfonyl group, C 2
  • Ruphonyl group c 2 _ 6 alkynylsulfonyl group, phenyl group, phenoxy group, phenylthio group, phenylsulfinyl group, phenylsulfonyl group, amino group, _ 6 alkylamino group, di (c ⁇ 6 alkyl) amino group , Shiano group, a nitro group, arsenate Dorokishi group, a benzyl group, Benjiruokishi group, an alkyl one carbonyl group or alkoxy, - or shows a force Lupo two group, form a Mechirenjiokishi groups become two X 1 Gar cord adjacent M may represent an integer of 0 to 3, and D 1 may be an oxygen atom, a sulfur atom, or a formula NR dl (where R dl represents a hydrogen atom or a 6 alkyl group). Group. Or a group represented by the formula
  • X 3 are the same or different halogen atoms, halogen in 1-3 amino optionally substituted 6 alkyl group, C 2 - 6 alkenyl group, C 2 _ 6 alkynyl group, 1 to 3 substituents may be substituted with halogen — 6 alkoxy groups, 1 to 3 substituents may be substituted with halogen C: _ 6 alkylthio group, C _ 6 alkylsulfinyl group, C!
  • R 2 and R 3 may be 1-3 substituted by halogen, respectively ⁇ - 6, or a salt thereof of [1], wherein a ⁇ alkyl group,
  • R 4 is selected from (1) a halogen atom, a C ⁇ e alkyl group optionally substituted with 1 to 3 halogen atoms, and a d-ealkoxy group optionally substituted with 1 to 3 halogen atoms.
  • One c C one or one C one CH—
  • Z is a halogen atom, a cyano group, 1-3 alkyl optionally substituted with 1 to 3 halogen atoms, a formula
  • R 17 represents (1) an alkyl group optionally substituted with 1 to 3 halogen atoms, or (2) (i) a halogen atom, and (ii) an alkyl group optionally substituted with 1 to 3 halogen atoms. shows the 19 Ararukiru group - substituted C DOO 6 alkyl group or (iii) halogen 1-3 amino optionally substituted be 1-3 substituents also a good alkoxy group C 7.
  • R 17X represents a hydrogen atom or a C ⁇ 6 alkyl group which may be substituted with 1 to 3 halogen atoms. Or a group represented by the formula
  • R 5h and R 6h each represent a hydrogen atom or an alkyl group which may be substituted with 1 to 3 halogen atoms.
  • R 14 is the above-mentioned [2] This shows the section according as defined above] with may be 1 are three substituted with a group represented - 6 alkyl group, (3) C 3 - e cycloalkyl alkyl group, (4) C 2 _ 6 alkenyl group, (5) CI- e alkoxy with 1-3 optionally substituted alkoxy group, (6) Shiano group, (7) a formyl group, or (8) hydrate
  • the compound according to the above-mentioned (1) which is a roxy group, or a salt thereof,
  • R 11 is a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, which may be substituted with 1 to 3 halogen atoms, a —6 alkylthio group, a —6 alkylsulfinyl group or a C 6 alkylsulfonyl group.
  • R 12 is a hydrogen atom, a halogen atom or a C ⁇ 6 alkyl group optionally substituted with 1 to 3 halogen atoms or a salt thereof,
  • R 1 is (1) halogen, C - have been 1-3 substituted with alkyl group, flicking 6 alkoxy group, e ⁇ alkylthio group, C 6 alkylsulfinyl group or a C ⁇ 6 alkyl sulfonyl Le group A phenyl group, (2) a naphthyl group, (3) a pyridyl group optionally substituted with 1 to 3 halogen atoms, (4) a quinolyl group, (5) an isoquinolyl group, and (6) a C ⁇ 4 alkyl group.
  • R 4 is (1) halogen or ⁇ - 6 alkyl group one to three substituents on these phenyl group or (2) C Medicine 6 alkoxy groups, one A- formula
  • I CIRUR 12 (wherein, the R 8 is a hydrogen atom or a ( ⁇ _ 6 alkyl group, R 9 is (0 hydrogen atom, (2) eight-necked Gen, hydroxy group, Ci-e alkoxy group , an alkylthio group, Al Kirusurufiniru group, C - 6 alkylsulfonyl group, 6 alkyl - force Lupo two Ruokishi group, hydroxy I amino group, 1 in Arukokishiimino group or 6 ⁇ alkyl Ichiriki Lupo sulfonyl O key Consequences amino group three optionally substituted C ⁇ 6 Al kill group, (3) C 3 - 6 cycloalkyl group, (4) C 2 - 6 alkenyl group, three 1 (5) 0 ⁇ 6 alkoxy group Optionally substituted Ci- 6 alkoxy group, (6) formyl group, (7) cyano group or (8) hydroxy group, R 1G is hydrogen atom, (2) eight-necked Gen
  • R 9p is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, L is a leaving group, and other symbols are as described in the above [1].
  • the compound represented by the formula or a salt thereof is subjected to an elimination reaction to obtain a compound represented by the formula
  • R 9p has the same meaning as described above, and the other symbols have the same meanings as described in the above [1].
  • a salt thereof Or a salt thereof with an oxidizing agent,
  • R 9q represents an optionally substituted acyl group, and other symbols have the same meanings as described in the above [1].
  • R 13 is optionally substituted one to three hydrogen atoms or halogen, respectively, (i) 6 alkyl group, a (ii) C 6 14 Ariru group or (iii) C 7 ⁇ 9 Ararukiru group, Other symbols have the same meanings as described in the above [1].) Or a salt thereof represented by the formula
  • R 14x represents a hydrogen atom or an alkyl group.
  • R 23 and R 24 each represent a hydrogen atom, a halogen atom, a 6- alkyl group or an alkoxy group, and Ph represents a phenyl group) or a salt thereof.
  • R 14y represents a Cj- 6 alkyl-carbonyl group optionally substituted by 13 halogens, and L 2 represents a leaving group
  • L 2 represents a leaving group
  • R 22 is an optionally 1 3 substituted with halogen, respectively (i) C 1 ⁇ alkyl group or (ii) (: me 6 alkyl one carbonyl group, L 6 represents a leaving group. )) Or a salt thereof;
  • R 25 is Ji may be 1-3 atoms substituted by halogen alkyl group, C 2 - 6 alkenyl group, a C 2 _ 6 alkynyl or phenyl group, q is an integer of 0 to 2
  • X la are the same or different and each represents a halogen atom or a C i alkyl group which may be substituted with 1 to 3 halogen atoms, and the other symbols are as defined in the above [1]. Reacting the compound or a salt thereof with an oxidizing agent,
  • R 26 represents an alkyl group, and other symbols have the same meanings as described in the above item [1].
  • R 26 has the same meaning as described above, and the other symbols have the same meanings as described in the above [1].
  • a salt thereof with an oxidizing agent R 26 S (0) p
  • R 9p has the same meaning as described above, and the other symbols have the same meanings as described in the above [1].
  • a salt thereof with a halogenating agent Or a salt thereof with a halogenating agent.
  • R 9P has the same meaning as described above, and the other symbols have the same meanings as described in the above [1].
  • L 1 is a halogen atom, a hydroxy group, — OS (O) C 1 or a formula
  • R 18 represents a hydrocarbon group which may be substituted.
  • Other symbols are as defined in the above [1].
  • R lx represents a hydrogen atom, a benzyl group or a tert-butyl group
  • R 9 p has the same meaning as described in the above [19], and other symbols have the same meanings as in the above [1].
  • R lx represents a hydrogen atom, a benzyl group or a tert-butyl group
  • R 9 p has the same meaning as described in the above [19]
  • other symbols have the same meanings as in the above [1].
  • [26] a method for weeding paddy weeds, which comprises applying the compound or salt thereof according to the above [1] to a paddy field;
  • the present invention provides
  • R 1 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • R 5 and R 6 are each a hydrogen atom, an optionally substituted hydrocarbon group, 59 99/04327
  • R 2 and R 3 each represent a hydrogen atom or a hydrocarbon group which may be substituted, or R 2 and R 3 may be substituted with an adjacent carbon atom, and May form a cyclic hydrocarbon group,
  • R 4 is an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • W 1 represents an oxygen atom or an optionally oxidized sulfur atom
  • R 7 represents an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group.
  • R 8 represents a hydrogen atom or an optionally substituted hydrocarbon group
  • R 9 represents a hydrogen atom, a cyano group, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group
  • R 15 represents a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group.
  • R 10 represents a hydrogen atom or an optionally substituted hydrocarbon group
  • R 11 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a formula
  • W 2 represents an oxygen atom or an optionally oxidized sulfur atom
  • R 16 represents a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or a substituted Represents an optionally substituted acyl group.
  • R 12 represents a hydrogen atom, a halogen atom or an optionally substituted hydrocarbon group,
  • Z represents a halogen atom, a cyano group, a hydrocarbon group which may be substituted, or an acyl group which may be substituted. ] Or a salt thereof,
  • R 1 is [LUC - e alkyl group, C 3 6 cycloalkyl group, C 2 6 alkenyl Le group, C 2 6 alkynyl group, C 6 - aryl radical, C 7 19 Ararukiru group, C 8 _ 20 ⁇ reel alkenyl groups and C 8 2C ⁇ reel alkynyl hydrocarbon group (the hydrocarbon group is an alkyl group selected from the group, if the alkenyl or alkynyl group, the hydrocarbon group,
  • halogen 1-3 amino optionally substituted alkyl group C 3 _ 6 Shikuroa alkyl group, C 2 6 alkenyl, C 2 6 alkynyl group, C 6 14 Ariru group, C 7 _ Interview 9 Ararukiru group, halogen 1-3 amino optionally substituted by C Bok 6 alkoxy group, C 2 _ 6 Arukeniruokishi group, C 2 6 Arukiniruokishi group, C 6 _ 14 7 Riruokishi group, C 7 19 Ararukiruokishi group , Formyl group, 6 alkyl carbonyl group, C 6 _ 14 aryl carbonyl group, 6 alkoxy-carbonyl group, C 6 _ 14 7 lyloxy-carbonyl group, C 7 19 aralkyl-carbonyl group, C 7 _ 19 ⁇ La Rukiruokishi - carboxymethyl group, which may be 1-3 amino substituted by halogen C ⁇ 6 alkyl group,
  • (10) a formyl group, an alkyl Ichiriki Ruponiru group, C 6 - 14 Ariru - carbonylation le group, C i-6 alkoxy one carbonyl group, C 6 _ 14 Ariruokishi one carbonyl group, C 7 _ 19 Ararukiru - carbonyl group, An acyl group selected from the group consisting of C 7 _ 19 aralkyloxy-carbonyl group, 5- to 6-membered heterocyclic carbonyl group, fused heterocyclic carbonyl group, and 5- to 6-membered heterocyclic acetyl group, wherein the acyl group is an alkylcarbonyl group or an alkoxy group; In the case of carbonyl group, hydroxy, cyano, sulfamoyl, mercapto, carboxy, alkylthio group, halogen atom, 6- alkoxy group, nitro group, alkoxy-carbonyl group, amino, mono- or di-6-alky
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, a condensed heterocyclic carbonyl group, or a 5- to 6-membered heterocyclic ring; for Asechiru groups, by 1 to 3 halogens optionally substituted alkyl group, ⁇ 3 _ 6 cycloalkyl group, C 2 _ 6 alkenyl, C 2 - 6 alkynyl group, a 1-3 substituted by halogen even if not good alkoxy group, a formyl group, C ⁇ - 6 alkyl one carbonyl group, (: 6 _ 14 ⁇ reel - carbonyl group, Ji 6 alkoxy - carbonyl group, C 6 - 14 Ariruoki Sheet - carbonyl group, C 7 _ 19 7 aralkyl - carbon
  • 2 ⁇ reel alkynyl hydrocarbon group selected from the group, (b) halogen 1-3 amino optionally substituted by C Bok 6 alkyl group, C 3 _ 6 cycloalkyl group, C 2 - 6 alkenyl group, C 2 _ 6 alkynyl, C 6 - 14 Ariru group, C 7 _ 19 Ararukiru groups, one to three optionally substituted alkoxy group with halogen, C 2 _ 6 Arukeniruokishi group, C 2 - 6 Arukini Ruokishi group, C 6 _ 14 Ariruokishi group, C 7 - 19 Ararukiruokishi group, formyl group, - 6 alkyl one carbonyl group, C 6 one 14 Ari Le one carbonyl group, 6 alkoxy Ichiriki Ruponiru group, C 6 - 14 Ariruokishi - carbonyl group, C 7 _ 19 Ararukiru - carbonyl group, C 7 -
  • 6 alkynylsulfinyl group, C 6 _ 14 ⁇ Li one Rusurufieru group may be 1-3 amino substituted by halogen E alkyl sulfonyl groups, C 2 - 6 alkenyl-sulfonyl group, C 2 _ 6 alkynylsulfonyl group, C 6 _ 14 ⁇ Li one Rusuruhoniru group, a nitro group, an amino group, a mono- or di-0 - 6 alkylamino group, hydroxy group, Shiano group , sulfamoyl group, mercapto preparative group, a halogen atom, 1-3 optionally substituted alkyl thio group halogen, C 2 _ 6 alkenyl Thio, rather it may also be substituted by one to three substituents selected from the group consisting of C 2 _ 6 alkynylthio and C 6 _ 14 7 Riruchio group, or two adjacent substituents
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, a condensed heterocyclic carbonyl group or a 5- to 6-membered heterocyclic group; for ring Asechiru groups, C i-6 alkyl le groups, C 3 - 6 cycloalkyl groups, C 2 - 6 alkenyl groups, C 2 - 6 alkynyl group, - 6 alkoxy group, a formyl group, an alkyl - carbonyl groups, C 6 - 14 ⁇ Li one Roux carbonyl group, ⁇ 6 alkoxy - carbonyl group, C 6 _ 14 7 Riruokishi - carbonyl group, C 7 - 19 Ararukiru one carbonyl group, C 7 _ 19 Ararukiruokishi one carbonyl group,
  • Q 1 is (a) hydrogen atom, optionally 1 to 5 atoms optionally substituted with (b) halogen (i) an alkyl group, (ii) C 3 - 6 cycloalkyl group, (iii) - 6 Alkenyl group, (iv) C 2 - 6 alkynyl group, (v) C 6 - 14 Ariru group, (vi) C 7 - 19 Ararukiru group, (vii) C 8 _ 2 . ⁇ reel alkenyl groups and (viii) C 8 - 2. Hydrocarbon group or (c) formyl, halogen 1-5 amino optionally substituted C ⁇ 6 alkyl one group selected from ⁇ reel alkynyl group, C 6 - 14 Ariru one carbonyl group,
  • Q 2 may be (a) 1 to 5 halogen-substituted (OC ⁇ 6 alkyl groups, (ii) C 3 _ 6 cyclo alkyl group, (iii) C 2 - 6 ⁇ alkenyl group, (iv) C 2 _ 6 alkynyl group, (V) C 6 - 14 Ariru group, (vi) C 7 - 19 ⁇ aralkyl group, (vii) C 8 - 20 ⁇ reel alkenyl groups and (viii) C 8 - -
  • a hydrocarbon group selected from arylalkynyl groups, and (b) one to three halogen-substituted It may also be ⁇ - 6 alkyl group, c 3 - 6 cycloalkyl group, c 2 - 6 alkenyl group, c 2
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 56-membered heterocyclic carbonyl group, a fused heterocyclic carbonyl group, or a 56-membered heterocyclic group; for Asechiru group, alkyl group, C 3 - 6 cycloalkyl group, C 2 - 6 alkenyl group, C 2 - 6 Arukini group, 6 alkoxy group, a formyl group, an alkyl Ichiriki Ruponiru group, C 6 _ 14 ⁇ Li one Lou carbonyl group, C i-e alkoxy one carbonyl group, C 6 - 14 ⁇ Riruokishi one carbonyl group, C 7 _ 19 Ararukiru one carbonyl group, C 7 - 19 ⁇ Rarukiruokishi one carbonyl group, a nitro group, an
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, a fused heterocyclic carbonyl group or a 5- to 6-membered group; If heterocyclic Asechiru group, alkyl group, C 3 - 6 cycloalkyl group, C 2 - 6 alkenyl group, C 2 - 6 Arukini group, an alkoxy group, a formyl group, CI- C6 alkyl one carbonyl group, C 6 ⁇ 14 aryl-carbonyl, C ⁇ _ 6 alkoxy-carbonyl, C 6 — 14 Riruokishi one carbonyl group, c 7 - 19 Ararukiru - carbonyl group, c 7 - 19 ⁇ Rarukiruokishi one carbonyl group, a nitro group, an amino
  • halogen 1 3 substituted 6 may be alkyl groups, C 3 _ 6 cycloalkyl group, C 2 - 6 alkenyl, C 2 - 6 alkynyl group, C 6 - 14 Ariru group, C 7 _ 19 7 aralkyl group, halogen 1 3 optionally substituted alkoxy group, C 2 _ 6 Arukeniruokishi group, C 2 - 6 Arukiniruokishi group, C 6 - 14 Ariruokishi group, C 7 _ 19 Ararukiruo alkoxy group, a formyl group, alkyl one carbonyl group, C 6 - 14 Ariru - Cal Poniru group, CI_ 6 alkoxy - Karuponiru group, C 6 _ 14 7 Riruokishi - force Lupo alkoxy group, a formyl group, alkyl one carbonyl group, C 6 - 14 Ariru - Cal Poniru group,
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, a fused heterocyclic carbonyl group or a 5- to 6-membered group; If heterocyclic Asechiru group, alkyl group, C 3 - 6 cycloalkyl group, C 2 - 6 alkenyl group, C 2 - 6 Arukini group, 6 alkoxy group, a formyl group, 6 alkyl - carbonyl group, C 6 - 14 Ariru - carboxymethyl sulfonyl group, C 6 alkoxy - carbonyl group, C 6 - 14 ⁇ Riruokishi - carbonyl group, C 7 _ 19 Ararukiru - carbonyl group, C 7 _ 19 ⁇ Rarukiruokishi - Karuponiru
  • the acyl group is an arylcarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic carbonyl group, a fused heterocyclic carbonyl group or a 5- to 6-membered group; If heterocyclic Asechiru groups, C DOO 6 alkyl groups, C 3 - beta cycloalkyl groups, C 2 - 6 alkenyl groups, C 2 _ 6 Arukini group, 0 I 6 alkoxy group, a formyl group, an alkyl one carbonyl group, C e - 14 Ariru - carbonyl group, - 6 alkoxy one carbonyl group, C 6 - 14 ⁇ Riruokishi - carbonyl group, C 7 - 19 Ararukiru - carbonyl group, C 7 _ 19 ⁇ Rarukiruokishi Ichiriki Ruponiru
  • R 14 is a hydrogen atom, ( ⁇ _ 6 alkyl group or halogen in 1-3 amino optionally substituted by C ⁇ 6 alkyl - shows the carbonylation Le group (Hereinafter, the substituent group (II)) may be substituted with 1 to 4 substituent groups selected from the group consisting of the groups represented by
  • the hydrocarbon group is a cycloalkyl group, an aryl group, an aralkyl group, an aryl alkenyl group or an arylalkynyl group
  • the hydrocarbon group is a substituent selected from the above substituent group ( ⁇ ), and is 1 to 5 halogen atoms.
  • One to five substituents may be substituted, and two adjacent substituents may be taken together to form a methylenedioxy group.
  • halogen 1-3 amino optionally substituted alkyl group C 3 _ 6 cycloalkyl Alkyl group, C 2 _ 6 alkenyl, C 2 - 6 alkynyl group, C 6 _ 14 Ariru group, C 7 _ 19 Ararukiru group, which may be 1-3 amino substituted by halogen C ⁇ - e alkoxy group, C 2 _ 6 alkenyloxy group, C 2 — 6 alkynyloxy group, C 6 — 14 aryloxy group, C 7 — 19 aralkyloxy group, formyl group, (: ⁇ 6 alkyl-monocarbonyl group, C 6 — 14 aryl) —Carbonyl group, ⁇ — 6 alkoxy—carbonyl group,
  • R 5 and R 6 are each a hydrogen atom, an optionally substituted hydrocarbon group (having the same meaning as in the above [1].) Or an optionally substituted heterocyclic group (the above [2] Represents the same meaning as.) Represents a group represented by),
  • R 2 and R 3 each represent a hydrogen atom or an alkyl group which may be substituted by 1 to 4 substituents selected from the above substituent group (A), or R 2 and R 3 27
  • R 4 is an optionally substituted hydrocarbon group (having the same meaning as in the above [1]), an optionally substituted heterocyclic group (having the same meaning as the above [2]), or a formula
  • W 1 represents an oxygen atom or a sulfur atom which may be mono- or di-oxidized
  • R 7 represents an optionally substituted hydrocarbon group (having the same meaning as in the above [1]) or substituted.
  • An optionally substituted heterocyclic group (having the same meaning as in the above [2].).
  • R 8 represents a hydrogen atom or an alkyl group which may be substituted by 1 to 4 substituents selected from the above substituent group (A), and R 9 represents a hydrogen atom, a cyano group, or a substituted
  • An optionally substituted hydrocarbon group having the same meaning as in the above [1]
  • an optionally substituted heterocyclic group having the same meaning as in the above [2]
  • an optionally substituted acyl group It has the same meaning as (10) in the above [1].
  • R 15 is a hydrogen atom, an optionally substituted hydrocarbon group (having the same meaning as in the above [1].) Or an optionally substituted heterocyclic group (having the same meaning as the above [2]. Represents a group represented by),
  • R 1 D represents a hydrogen atom or a C 6 alkyl group which may be substituted with 1 to 4 substituents selected from the above substituent group (A);
  • R 11 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group (having the same meaning as in [1] above), and an optionally substituted heterocyclic group (having the same meaning as in [2] above.) )
  • R 11 is a hydrogen atom, a halogen atom, an optionally substituted hydrocarbon group (having the same meaning as in [1] above), and an optionally substituted heterocyclic group (having the same meaning as in [2] above.)
  • W 2 is an oxygen atom or a sulfur atom which may be mono- or dioxidized
  • R 16 is a hydrogen atom, a hydrocarbon group which may be substituted (showing the same meaning as the above [1].)
  • an optionally substituted heterocyclic group having the same meaning as in the above [2]
  • an optionally substituted acyl group having the same meaning as (10) in the above [1].
  • R 12 represents a hydrogen atom, a halogen atom or a C alkyl group which may be substituted with 1 to 4 substituents selected from the above substituent group (A),
  • the carbon atom to which R 8 is bonded is bonded to the nitrogen atom of the amide, and R 9 or The carbon atom to which is bonded is bonded to the carbon atom to which Z is bonded.
  • Z is a halogen atom, a cyano group, a 6- alkyl group optionally substituted with 1 to 4 substituents selected from the above-mentioned substituent group (A), or an optionally substituted acyl group (above [ The compound of the above-mentioned [42], which has the same meaning as (10) in 1), or a salt thereof,
  • R 1 is the formula
  • X 1 is the same or different and is substituted with 1 to 3 halogen atoms or halogens which may be an alkyl group, c 2 - e alkenyl, c 2 _ 6 alkynyl group, which may be 1-3 amino substituted with C androgenic ( ⁇ - 6 alkoxy groups, C 2 - 6 alkenyl Okishi groups, C 2 _ 6 alkynyloxy groups, optionally substituted with 1 to 3 halogens
  • Bok 6 alkylthio group, C 2 - 6 alkenylthio group, C 2 _ 6 alkynylthio may be 1-3 amino substituted by halogen 6 alkylsulfinyl group, C 2 _ 6 ⁇ Luque Nils sulfinyl groups, C 2 - 6 alkynylsulfinyl group, substituted by 1 to 3 halogens which may be an alkylsulfonyl group, C 2 - 6 Arukenirusu Ruhoniru group, C 2 _ 6 alkynyl-sulfonyl group, phenyl group, phenoxy group, Hue two thio groups, Hue Nils sulfinyl group, phenylpropyl sulfonylamino group, an amino group, ⁇ - 6 alkylamino group, di (C ⁇ 6 alkyl) amino group, Shiano group, a nitro group, arsenate
  • X 3 are the same or different halogen atoms, halogen in 1-3 amino optionally substituted C bets 6 alkyl group, which may be 1-3 amino substituted by halogen C bets 6 alkoxy groups, halogen 1-3 amino optionally substituted alkylthio group, C - 6 alkylsulfinyl group, C - 6 alkylsulfonyl group, 6 Al kills one carbonyl group, ⁇ - 6 alkoxy one carbonyl group, phenoxy group, Shiano group or a nitro group,
  • n represents an integer of 0 to 3
  • D 2 represents an oxygen atom, a sulfur atom, or wherein NR d2 (wherein, R d2 is a hydrogen atom, or a ⁇ 3 Bok 6 alkyl group )). Wherein R 2 and R 3 may each be substituted with 1 to 3 halogens.
  • R 4 is selected from (1) a halogen atom, a C j- 6 alkyl group optionally substituted with 1 to 3 halogen atoms and a C ⁇ 6 alkoxy group optionally substituted with 1 to 3 halogen atoms.
  • Z is an octogen atom, a cyano group, or a formula
  • R 17 is (1) an alkyl group optionally substituted with 1 to 3 halogen atoms, or (2) (i) a halogen atom, and (ii) an alkyl group optionally substituted with 1 to 3 halogen atoms. It represents an C 6 alkyl group or (iii) eight androgenic in 1-3 amino which may be substituted is 1 to 3 substituents also a good alkoxy group optionally C 7 _ 19 Ararukiru group. ]
  • the compound according to the above-mentioned [42] which is a group represented by the formula or a salt thereof,
  • R 8 is compound or a salt thereof of the above [42], wherein a hydrogen atom or a ⁇ Bok 6 alkyl group,
  • R 11 and R 12 are each a hydrogen atom, a halogen atom or a halogen which may be 1-3 substituents C ⁇ - 6 compound or its salt of the above [42], wherein an alkyl radical and,
  • R 1 is (1) halogen, C - 6 alkyl group, C - 6 alkoxy group, (: City 6 ⁇ alkylthio group, at C _ 6 alkyl sulfide alkylsulfonyl group or a C _ 6 alkyl sulfonyl Le group 1 to 3 optionally substituted (i) phenyl or (ii) naphthyl or (2) halogen or 1 to 3 carbon atoms optionally substituted with 1 to 3 halogens
  • a substituted or unsubstituted phenyl or an optionally substituted rubamoyl group, R 2 and R 3 each represent an alkyl group, and R 4 represents 1-3 substituted halogens.
  • R 8 is a (i) hydrogen atom or (iDC ⁇ e alkyl group
  • R 9 is (i) halogen, hydroxy, Ji 6 alkoxy, alkyl - carbonyl O carboxymethyl, hydroxy Shiimino, Arukokishiimino or Asetokishiimino in 1-3 amino optionally substituted alkyl group, ( ⁇ ) 3 -.
  • the compound represented by the general formula (I) may have two or more stereoisomers (for example, enantiomers).
  • General formula (I) includes all of these stereoisomers and a mixture of any two or more of them.
  • the compound represented by the general formula (I) may have two or more geometric isomers (for example, E / Z or each isomer of trans / cis, each isomer of S-trans / S-cis, etc.) Force S exists, but the general formula (I) includes all of these geometric isomers and any of them Mixtures of two or more are included.
  • Examples of the hydrocarbon group in the optionally substituted hydrocarbon group represented by R 1 include an aliphatic group which may have a linear, branched or cyclic double bond or triple bond, an aryl group or an aralkyl group. And the like. Specific examples include an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an aryl group, an aralkyl group, an aryl-alkenyl group, and an aryl-alkynyl group.
  • the alkyl group preferably includes a linear or branched alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, te-butyl. , N-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl and other 6- alkyl groups are used.
  • the cycloalkyl group is preferably a cycloalkyl group having 3 to 6 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
  • the alkenyl group is preferably a straight-chain or branched alkenyl group having 2 to 6 carbon atoms, for example, aryl, isopropenyl, isobutenyl,
  • the cycloalkenyl group is preferably a cycloalkenyl group having 3 to 6 carbon atoms, for example, 1- or 2-cycloprobenyl, 1- or
  • C 3 _ 6 cycloalkenyl, etc., such as cyclohexenyl can be used.
  • the alkynyl group preferably include an alkynyl group having 2 to 6 carbon atoms, for example propargyl, 2 - heptynyl, 3 - heptynyl, 3-pentynyl, etc.
  • C 2 _ 6 alkynyl group hexynyl, etc., to 3 is used Can be
  • the aryl group preferably includes an aryl group having 6 to 14 carbon atoms, and examples thereof include phenyl, naphthyl, and anthryl.
  • Ararukiru group 1 9 7 carbon atoms such as benzyl, phenethyl, phenyl, such as phenylpropyl - C Bok 4 alkyl, benzhydryl, trityl and the like are used.
  • one Ruarukeniru groups preferably include Ari Ruarukeniru group 0 2 to 8 carbon atoms, for example, styryl, C 6 _ 1 4 ⁇ Li one Roux C 2 such as cinnamyl - 6 alkenyl and the like Used.
  • Ariru one alkynyl group preferably include Ari Ruarukiniru group 0 2 to 8 carbon atoms, e.g., C 6, such as Fueniruechiniru - 1 4 ⁇ Li one Roux C 2 - 6 alkynyl and the like are used.
  • the hydrocarbon group is an alkyl group, an alkenyl group or an alkynyl group
  • the hydrocarbon group is, for example, a hydroxy group, an amino group, a cyano group, a sulfamoyl group, a sulfamoyloxy group, a mercapto group, a nitro group,
  • a halogen atom eg, fluorine, chlorine, bromine, iodine
  • an optionally substituted heterocyclic group an optionally substituted acyl group
  • An optionally substituted hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted acyl group, T is O, one S (O) k- (k represents 0, 1 or 2) or A group represented by the formula:
  • Q 1 represents a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted acyl group
  • Q 2 represents an optionally substituted hydrocarbon group or an optionally substituted hydrocarbon group. May represent a hydroxyl group, or Q 1 and Q 2 may form a ring together with an adjacent nitrogen atom.
  • R 14 is substituted with 1 to 3 hydrogen atoms, alkyl groups (eg, methyl, ethyl, n-propyl, isopropyl, etc.) or halogens (eg, fluorine, chlorine, bromine, iodine) also alkyl - Cal Boniru group (eg, Asechiru, propionyl, Puchiriru, Isopuchiriru etc.) groups represented by shows the], C 3 _ 6 cycloal
  • the hydrocarbon group is a cycloalkyl group, a cycloalkenyl group, an aryl group, an aralkyl group, an aryl alkenyl group or an aryl alkynyl group
  • the hydrocarbon group is selected from the above substituent group ( ⁇ ′).
  • Substituents 1 to 5 (preferably 1 to 3) alkyl groups which may be substituted with halogen (eg, methyl, ethyl, ⁇ -propyl, isopropyl, ⁇ -butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, trifluoromethyl, etc.
  • halogen eg, methyl, ethyl, ⁇ -propyl, isopropyl, ⁇ -butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, n-hexyl, isohexyl, trifluoromethyl, etc.
  • — 6 alkyl groups ⁇ haloalkyl groups
  • cycloalkyl groups eg, cyclopropyl , cyclobutyl, cyclopentyl, C 3 _ 6 cycloalkyl group cyclohexyl, etc.
  • cyclohexylene cyclohexylene
  • an alkenyl group e.g., Ariru, isoproterenol base two Le, isobutenyl, 1-Mechiruariru, 2-Bae Nparu, C 2 _ 6 alkenyl groups such as cyclohexenyl 2
  • a cycloalkenyl group e.g., 1 - or 2-Shikuropuro Bae alkenyl, 1 - or 2-cyclobutenyl, 1 —, 2- or 3-cyclopentenyl, 1-, 2- or 3-cyclo to C such as cyclohexenyl 3 - 6 cycloalkenyl group
  • alkynyl group eg, Puroparugi Le, 2-heptynyl, 3-heptynyl, 3-pentynyl, C 9 of hexynyl, etc., to 3 - 6 alkynyl group
  • Examples of the hydrocarbon group represented by Q °, Q 1 , and Q 2 include the same hydrocarbon groups as those described above for the optionally substituted hydrocarbon group represented by R 1 .
  • the hydrocarbon group represented by Q °, Q 1 , and Q 2 has 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, and iodine) as substituents. .
  • halogen atoms eg, fluorine, chlorine, bromine, and iodine
  • the carbamoyl group, the carbamoyloxy group, the urido group or the thiocarbamoyl group is a hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted acyl group. Or two or more may be substituted the same or different.
  • the hydrocarbon group include the same as the hydrocarbon group in the optionally substituted hydrocarbon group represented by R 1 .
  • the optionally substituted heterocyclic group and the optionally substituted acyl group are described in detail below.
  • examples of the heterocyclic group in the optionally substituted heterocyclic group include a nitrogen atom (which may be oxidized), an oxygen atom, and a sulfur atom (which may be mono- or di-oxidized).
  • aziridinyl eg, 1- or 2-aziridinyl
  • azilinyl eg, 1- or 2-azilinyl
  • azetyl eg, 2-, 3- or 4- azetyl
  • azetidinyl eg, 1 1,2- or 3-azetidinyl
  • p-hydroazepinyl eg, 1-, 2-, 3- or 4-perhydroazepinyl
  • p-hydroazocinyl eg, 11, 2-, 3-, 4) 1- or 5-perhydroazoshell
  • pyrrolyl eg, 1-, 2- or 3-pyrrolyl
  • pyrazolyl eg, 1-, 3-, 4- or 5-pyrazolyl
  • imidazolyl eg, 1-, 2- , 4- or 5-imidazolyl
  • triazolyl eg, 1, 2, 3-triazolyl 1-, 41- or 5-yl, 1, 2, 4-triazole-1-, 31-, 41
  • the heterocyclic group is an alkyl group which may be substituted with 1 to 3 halogen atoms (eg, fluorine, chlorine, bromine, iodine) (eg, methyl, ethyl, n-propyl, isopropyl, n-butyl).
  • halogen atoms eg, fluorine, chlorine, bromine, iodine
  • ⁇ Li one Rusurufiniru group e.g., C 6, such as Hue Nils sulfinyl - 14 ⁇ Li one Rusuru Finiru
  • halogen e.g., fluorine, chlorine, bromine, iodine
  • alkylsulfonyl group e.g., methylsulfonyl, etc.
  • Echirusuruho sulfonyl ( ⁇ _ 6 alkylsulfonyl), ⁇ Luque sulfonyl sulfonyl group (e.g., Ariru sulfonyl, isoproterenol base Nirusuruhoniru, C 2 _ 6 ⁇ Luque sulfonyl sulfonyl such isobutenyl sulfonyl), alkynylsulfonyl (e.g., propargyl sulfonyl le, 2- heptynyl C 2 _ 6 alkynyl sulfonyl such as sulfonyl, 3-butynylsulfonyl) , Arylsulfonyl groups (eg, C G _ 14 such as phenylsulfonyl) Arylsulfonyl), nitro group, amino group, mono- or di-C
  • Isobuentuchio such Isopuchiruchio - 6 alkenylthio
  • alkynylthio e.g., propargylthio, 2-Petit two thio, 3-Petit two C 2 _ 6 alkynylthio
  • Ariruchio groups Lucio etc. e.g., the same or different 1 to 3 substituents selected from the group consisting of C 6 _ 1 4 7 Riruchio
  • two adjacent substituents may be taken together to form a methylenedioxy group.
  • acyl group in the optionally substituted acyl group refers to an acyl group having 1 to 20 carbon atoms derived from an organic carboxylic acid.
  • an alkanol group preferably an alkanoyl group having 1 to 7 carbon atoms (eg, an alkyl-carbonyl group such as formyl or acetyl, propionyl, butyryl, isobutyryl, pentanoyl, hexanoyl, heptanyl, etc.)
  • an alkenylcarbonyl group preferably Alkenylcarbonyl group having 2 to 6 carbon atoms (eg, arylcarbonyl, isopropenylcarbonyl, isobutenylcarbonyl, 1-methylarylcarbonyl, 2-pentenylcarbonyl, 2-hexenylcarbonyl, etc.)
  • alkynylcarbonyl Groups preferably alkynylcarbonyl groups having 2
  • Naphthyl- such as luponyl and naphthylethylcarbonyl, aralkyloxycarbonyl group, preferably aralkyloxycarbonyl group having 7 to 19 carbon atoms (eg, benzyloxycarbonyl, phenethylo) Phenyl C i _ 4 alkyloxycarbonyl such as xycarbonyl, phenylpropyloxycarbonyl, etc., 5- to 6-membered heterocyclic carbonyl group or fused heterocyclic carbonyl group (eg, 2- or 3-pyrrolylcarbonyl) Pyrrolylcarbonyl, 3-, 4- Pyrazolyl carbonyl such as 5-pyrazolyl carbonyl, 2-, 4 — Or imidazolylcarbonyl, such as 5-imidazolylcarbonyl, 1,2,3-triazolyl—4-ylcarbonyl, 1,2,4-triazolylcarbon
  • Carbohydrates such as indolylcarbonyl, 2-, 3- or 4-pyranylcarbonyl Thiopyranylcarbonyls such as phenyl, 2-, 3- or 4-thiopyranylcarbonyl; quinolylcarbonyls such as 3-, 4-, 5-, 6-, 7- or 8-quinolylcarbonyl; isoquinolylcarbonyl; Pyrido [2,3-d] pyrimidinylcarbonyl (eg, pyrido [2,3-d] pyrimidine-1-ylcarbonyl), 1,5—, 1,6—, 1,7—, 1, Naphthyridinylcarbonyl (eg, 1,5-naphthyridin-2- (or 3-ylcarbonyl)), thieno [2,3-d) pyridyl, such as 8—, 2, 6— or 2,7-naphthyridinylcarbonyl Carbonyl (eg, thieno [2,3-d] pyridine-3
  • acyl group is an alkylcarbonyl group, an alkenylcarbonyl group, an alkynylcarbonyl group, an alkoxycarbonyl group, an alkenyloxycarbonyl group or an alkynyloxycarbonyl group, 1-3 substituents of hydroxy, cyano, sulfamoyl, mercapto are used as the substituent.
  • alkylthio groups eg, alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, isobutylthio
  • halogen atoms eg, fluorine, chlorine, bromine, iodine
  • alkoxy groups eg, methoxy , Ethoxy, n-propoxy, tert- Alkoxy groups such as toxic, n-hexyloxy, etc., nitro group, alkoxyl carbonyl group (eg, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxy) C.
  • alkoxyl carbonyl group eg, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbon
  • alkoxy-carbonyl group such as carbonyl, tert-butoxycarbonyl, etc.
  • amino, alkylamino group eg, methylamino, ethylamino, n-propylamino, n-butylamino, tert-butylamino, n_pentylamino, n-
  • Mono or di such as hexylamino, dimethylamino, jetiamino, methylethylamino, di (n-propyl) amino, di (n-butyl) amino, alkylamino group, alkoxyimino group (eg, methoxyimino) , Et Shiimino, II one Puropokishiimino, t er t-butoxide Kishiimino, Kishiruokishi to n-- imino etc. - 6 Arukokishiimino group) may have a like human Dorokishiimino
  • the acyl group is a cycloalkylcarbonyl group, an arylcarbonyl group, a cycloalkyloxycarbonyl group, an aryloxycarbonyl group, an aralkylcarbonyl group, an aralkyloxycarbonyl group, a 5- to 6-membered heterocyclic ring;
  • a carbonyl group, a condensed heterocyclic group, or a 5- to 6-membered heterocyclic acetyl group one to three alkyl groups which may be substituted with halogen (eg, fluorine, chlorine, bromine, iodine)
  • halogen eg, fluorine, chlorine, bromine, iodine
  • a cycloalkyl group e.g., cyclopropyl, cyclobutyl, cyclopentyl, C 3 _ 6 Shikuroa such alkoxy Le cyclohexane Kill
  • alkenyl group e.g., Ariru, isoproterenol base alkenyl, isobutenyl, 1 Mechiruariru, 2-pentenyl, C 2, such as cyclohexenyl 2 - 6 alkenyl
  • cycloalkenyl group e.g., Shikuropuro base alkenyl, Shikurobute alkenyl, cycloalkyl pentenyl, C 3, such as cyclohexenyl - 6 cycloalkenyl
  • alkynyl group e.g., propargyl, 2 - heptynyl, 3 - heptynyl, 3 - pentynyl, C
  • hexenyl ylcarbonyl to 2) C 2 - 6 alkynyl chromatography carbonyl (eg, propargyl carbonyl, 2-Petit two Luke Ruponiru, 3 - Petit alkenyl carbonyl, 3-pentynyl carbonyl, 3-to carboxy sulfonyl carbonyl, etc.), C 3 - 6 cycloalkyl - carbonyl (e.g., Shikuropuropi ylcarbonyl, cycloalkyl Petit Luca Lupo alkenyl, cyclopentyl Luca Lupo alkenyl, cyclohexyl carbonyl cyclohexylene, etc.) C 6 - 14 Ariru one carbonyl (e.g., Benzoiru naphthoquinone evening Ren carbonyl, etc.), E alkoxy one carbonyl (eg, Metokishika Ruponiru, ethoxycarbonyl, propoxy
  • Specific examples of the group represented by the formula —T1 include, for example, an alkyloxy group, a cycloalkyloxy group, an alkenyloxy group, a cycloalkenyloxy group, an alkynyloxy group, an aryloxy group, an aralkyloxy group, an arylalkylalkoxy group, Arylalkynyloxy group, heterocyclic oxy group, acyloxy group, alkylthio group, cycloalkylthio group, alkenylthio group, cycloalkenylthio group, alkynylthio group, arylaryl group, aralkylthio group, arylalkylalkenylthio group, arylarylalkynylthio Group, heterocyclic thio group, acylthio group, alkyldithio group, aryldithio group, aralkyldithio group, alkylsulfin
  • the alkyloxy group preferably includes a linear or branched alkyloxy group having 1 to 6 carbon atoms, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, Tert-butoxy, n-pentyloxy, sec-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy and the like are used.
  • a linear or branched alkyloxy group having 1 to 6 carbon atoms such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, Tert-butoxy, n-pentyloxy, sec-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, isohexyloxy and the like are used.
  • the cycloalkyloxy group is preferably a cycloalkyloxy group having 3 to 6 carbon atoms, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and the like.
  • the alkenyloxy group preferably includes a linear or branched alkenyloxy group having 2 to 6 carbon atoms, such as aryloxy, isopropenyloxy, 1-butenyloxy, 2-pentenyloxy, and 2-alkenyloxy. Xenyloxy or the like is used.
  • Examples of the cycloalkenyloxy group preferably include a cycloalkenyloxy group having 3 to 6 carbon atoms, for example, cyclopropenyloxy, cyclobutenyloxy, cyclopentenyloxy, cyclohexenyloxy and the like. It is.
  • the alkynyloxy group is preferably an alkynyloxy group having 2 to 6 carbon atoms, and for example, pulpargyloxy and the like are used.
  • the aryloxy group is preferably an aryloxy group having 6 to 14 carbon atoms, and examples thereof include phenoxy and naphthyloxy.
  • the aralkyloxy group is preferably an aralkyloxy group having 7 to 19 carbon atoms, and for example, a phenyl- 4- alkyloxy group such as benzyloxy, phenethyloxy, phenyloxypyroxy and the like are used.
  • ⁇ reel alkenyl O alkoxy group preferably a C 6 such as ⁇ reel alkenyl O alkoxy group and the like, for example Suchiriruokishi of 0 2 to 8 carbon atoms - 1 4 ⁇ Li one Roux C 2 - 6 Arukeniruokishi group Is used.
  • Examples of the ⁇ reel alkynyl O carboxy groups preferably include ⁇ reel alkynyl O carboxy groups 0 2 to 8 carbon atoms, for example, phenylalanine E Hee Ruo carboxymethyl Flip like 6 _ 1 4 Ariru - C 2 _ 6 alkynyl An oxy group is used.
  • Any of these groups may be substituted with 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • halogen atoms eg, fluorine, chlorine, bromine, iodine.
  • the heterocyclic oxy group includes a group represented by the formula T′—O— (O ′)
  • pyrrolyloxy eg, 2- or 3-pyrroloxy
  • pyrazolyloxy Eg, 3-, 4- or 5-birazoloxy
  • imidazolyloxy eg, 2-, 4- or 5-imidazolyloxy
  • triazolyloxy eg, 1, 2, 3-triazolyloxy
  • tetrazolyloxy eg, 1H- or 2H-tetrazole-5-yloxy
  • furyloxy eg, 2- or 31-furyloxy
  • chenyloxy eg, 2 — Or 3-Chenyloxy
  • Chenyloxy with sulfur atom oxidized eg, 2- or 3-Chenyl 1, 1-dioxydoxy
  • Oxazolyloxy Eg, 2, 4 one or 5- old Kisazoriruokishi
  • the acyloxy group may be a group represented by the formula T ′ ′ 1 0— (Shows the same meaning as the optionally substituted acyl group included in ( ⁇ ')). Specific examples thereof include acetoxy, propionyloxy, ptyryloxy, pentanoyloxy, and C 6- alkyl such as xanyloxy-carbonyloxy, fenir , C!
  • the alkylthio group preferably includes a linear or branched alkylthio group having 1 to 6 carbon atoms, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, and the like.
  • Tert-butylthio, n-pentylthio, sec-pentylthio, isopentylthio, neopentylthio, n-hexylthio, isohexylthio, etc. are used.
  • the cycloalkylthio group is preferably a cycloalkylthio group having 3 to 6 carbon atoms, for example, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio and the like.
  • the alkenylthio group preferably includes a straight-chain or branched alkenylthio group having 2 to 6 carbon atoms, such as arylthio, isopropylenylthio, 1-butenylthio, 2-pentenylthio, and 2-alkenylthio. Hexenylthio and the like are used.
  • the cycloalkenylthio group is preferably a cycloalkenylthio group having 3 to 6 carbon atoms, and examples thereof include cycloprobenylthio, cyclobutenylthio, cyclopentenylthio, cyclohexenylthio and the like.
  • the alkynylthio group is preferably an alkynylthio group having 2 to 6 carbon atoms, for example, propargylthio and the like.
  • the arylthio group is preferably an arylthio group having 6 to 14 carbon atoms, for example, phenylthio, naphthylthio and the like.
  • the aralkylthio group is preferably an aralkylthio group having 7 to 19 carbon atoms, for example, a phenyl Ci- 4 alkylthio group such as benzylthio, phenylethylthio, phenylpropylthio and the like.
  • a heteroarylthio group preferably include ⁇ reel alkenylene Lucio groups 0 2 to 8 carbon atoms, for example C 6 _ 4 ⁇ reel one C 2 _ 6 alkenylthio groups such Suchiriruchio is used.
  • a heteroarylthio group preferably a C 6 to include ⁇ reel alkynylene Lucio groups 0 2 to 8 carbon atoms, such as phenylene Ruechi two thio - 6 alkynylthio - 1 4 Ariru one C 2 Used.
  • Each of these groups is 1 to 5 (Preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • heterocyclic thio group examples include groups represented by the formula T′—S— ( ⁇ ′ has the same meaning as described above), and specifically, pyrrolylthio (eg, 2— or 3-pyrrolylthio) , Birazolylthio (eg, 3-, 4- or 5-birazolylthio), imidazolylthio (eg, 2-, 4- or 5-imidazolylthio), triazolylthio (eg, 1, 2, 3-triazole-4-ylthio, 1 , 2,4-triazolyl-5-ylthio), tetrazolylthio (eg, 1H— or 2 ⁇ -tetrazole-5-ylthio), furylthio (eg, 2— or 3—furylthio), thienylthio (eg, 2—or 3-Chenylthio), Chenylthio in which the sulfur atom of the phenyl group is oxidized (eg, 2— or 3—Chenyl 1,
  • acylthio group examples include a group represented by the formula T ′ ′-S— ( ⁇ ′′ has the same meaning as described above). Specifically, acetylthio, propionylthio, butyrylthio, pentanoylthio, 0 Bok 6 alkyl one carbonylation Lucio such Kisanoiruchio, benzyl carbonylation thio, phenylene Lou C i _ 4 alkyl carbonylation Lucio such Fuenechirukarubo two thio, Benzoiruchio, C such Nafutoiruchio 6 -] 4 ⁇ Li one Rukarupo two Lucio , Carbenylthiol, benzoenylcarbonylthio and the like are also used.
  • the alkyldithio group is preferably a straight-chain or branched alkyldithio group having 1 to 6 carbon atoms, for example, methyldithio, ethyldithio, n-propyldithio and the like.
  • aryldithio group preferably, an aryldithio group having 6 to 14 carbon atoms is used, and for example, phenyldithio, naphthyldithio and the like are used.
  • the aralkyldithio group is preferably an aralkyldithio group having 7 to 19 carbon atoms, for example, a phenyldialkyldithio group such as benzyldithio and phenethyldithio.
  • the alkylsulfinyl group is preferably a straight-chain or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as methylsulfinyl, ethylsulfinyl, ⁇ -propylsulfinyl, isopropylsulfenyl, and n- Xylsulfinyl and the like are used.
  • the alkenylsulfinyl group is preferably a straight-chain or branched alkenylsulfinyl group having 2 to 6 carbon atoms, for example, arylsulfinyl and the like.
  • the arylsulfinyl group is preferably an arylsulfinyl group having 6 to 14 carbon atoms, for example, phenylsulfinyl and the like.
  • ⁇ Lal Kill sulfinyl group preferably include ⁇ La Ruki Rusuru arylsulfinyl group having 1 9 7 carbon atoms, for example, base Nji Rusuru Fini phenyl _ C Bok 4 alkylsulfinyl such as Le is used.
  • Each of these groups (alkyldithio group, aryldithio group, aralkyldithio group, alkylsulfinyl group, alkenylsulfinyl group, arylsulfinyl group, aralkylsulfinyl group) has 1 to 5 (preferably 1 to 3) groups. It may be substituted by a halogen atom (eg, fluorine, chlorine, bromine, iodine).
  • a halogen atom eg, fluorine, chlorine, bromine, iodine
  • heterocyclic sulfinyl group examples include a group represented by the formula T'-iSO- ( ⁇ 'has the same meaning as described above), and specifically, pyrrolylsulfiel (eg, 2- or 3-pyrrolidyl) Rusulfinyl), birazolylsulfinyl (eg, 3-, 4- or 5-birazolylsulfinyl) and the like.
  • the alkylsulfonyl group is preferably a straight chain having 1 to 6 carbon atoms or Examples thereof include a branched alkylsulfonyl group, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, and isopropylsulfonyl.
  • the alkenylsulfonyl group is preferably a straight-chain or branched alkenylsulfonyl group having 2 to 6 carbon atoms, for example, arylsulfonyl and the like.
  • the arylsulfonyl group is preferably an arylsulfonyl group having 6 to 14 carbon atoms, for example, phenylsulfonyl, naphthylsulfonyl and the like.
  • ⁇ Lal Kill sulfonyl group preferably include Araru alkylsulfonyl group having 1 9 7 carbon atoms, for example base Njirusuruhoniru, Fuenechirusuruho sulfonyl, phenyl, such as phenylpropyl sulfonyl - is C Bok 4 alkylsulfonyl group Used.
  • Each of these groups (alkylsulfonyl group, alkenylsulfonyl group, arylsulfonyl group, aralkylsulfonyl group) has 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine) , Iodine).
  • halogen atoms eg, fluorine, chlorine, bromine
  • heterocyclic sulfonyl group examples include a group represented by the formula T′-S ⁇ 2 — (where ⁇ ′ is as defined above), and specifically, pyrrolylsulfonyl (eg, 2- Is 3-pyrrolylsulfonyl), birazolylsulfonyl (eg, 3-, 4- or 5-birazolylsulfonyl).
  • pyrrolylsulfonyl eg, 2- Is 3-pyrrolylsulfonyl
  • birazolylsulfonyl eg, 3-, 4- or 5-birazolylsulfonyl
  • Examples of the group represented by ⁇ include: (1) an alkylamino group, preferably a mono- or di- (alkyl having 1 to 6 carbon atoms) amino group (eg, methylamino, ethylamino, n-propylamino, n-propylamino —Butylamino, tert-butylamino, n-pentylamino, n-hexylamino, dimethylamino, getylamino, methylethylamino, di- (n-propyl) amino, di- (n-butyl) amino, etc.), (2) Cycloalkylamino group, preferably mono or di (cycloalkyl having 3 to 6 carbon atoms) amino group (for example, cyclopropylamino, cyclopentylamino, cyclohexylamino, dicyclohexylamino, etc.), 3arylamino group, preferably Ariruamin
  • heterocyclic group in the above shows the heterocyclic group in the optionally substituted heterocyclic group included in the above-mentioned substitution group ( ⁇ ').
  • 1 to 4 may be substituted with 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • group ⁇ ′′ in 5 represents a hydrocarbon group
  • this group is replaced with 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • group ⁇ ′ ′′ or ⁇ ′′ ′′ represents a 6- alkyl carbonyl group
  • these groups may have 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine) , Chlorine, bromine, iodine).
  • Q 1 and Q 2 may form a ring together with an adjacent nitrogen atom, preferably a 3- to 7-membered ring (eg, pyrrolidino, piperidino, morpholino, thiomorpholino, 1-pi Radinyl, aziridino, etc.) may form the formula on nnsMo
  • Groups preferably mono- or di- (alkyl having 1 to 6 carbon atoms) sulfamoyl groups (eg methylsulfamoyl, ethylsulfamoyl, n-propylsulfamoyl, n-hexylsulfamoyl, dimethylsulfamoyl, jeti) Rusulfamoyl, methylethylsulfamoyl, di (n-butyl) sulfamoyl, etc.), (2) cycloalkylsulfamoyl group, preferably a cycloalkylsulfamoyl group having 3 to 6 carbon atoms (eg, cyclopropylsulfamoyl) , Cyclohexylsulfamoyl, etc.), 3 arylsulfamoyl group, preferably an arylsulfamoyl group having 6 to 14 carbon
  • each symbol is to indicate to the same meaning as defined above
  • represented by e.g., such as ⁇ cetyl sulfamoyl E alkyl force Lupo acylsulfamoyl, benzyl Cal Po Nils Alpha Phenyl such as moyl, etc. Heterocycles such as alkyl rubonylsulfamoyl, phenylcarbonylsulfamoyl, etc.
  • 1 to 5 for each of the groups 1 to 4 (Preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • ⁇ ′ ′′ represents a hydrocarbon group
  • this group may be substituted with 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • T '"orT""is C] - 6 may exhibit alkylcarbonyl el groups, these groups 1-5 pieces (preferred Or 1 to 3 halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • Q 1 and Q 2 may form a ring together with an adjacent nitrogen atom, and may form, for example, pyrrolidino, piperidino, morpholino, thiomorpholino, 1-piperazinyl, aziridino, azetidino and the like.
  • an alkylsulfonyloxy group preferably an alkylsulfonyloxy group having 1 to 6 carbon atoms (for example, methanesulfonyloxy, Ethanesulfonyloxy, etc.), 2arylsulfonyloxy group, preferably an arylsulfonyloxy group having 6 to 14 carbon atoms (eg, benzenesulfonyloxy, etc.), 3aralkylsulfonyloxy group An aralkylsulfonyloxy group preferably having 7 to 19 carbon atoms (for example, phenyl-alkylsulfonyloxy such as benzylsulfonyloxy, phenethylsulfonyloxy, etc.); (for example, ⁇ cetyl sulfonyl O carboxymethyl, C WINCH such butyryl
  • Each of 1 to 3 is:! It may be substituted with up to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • the C alkyl group sulphonyloxy group may be substituted by 1 to 5 (preferably 1 to 3) halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • R 1 examples include the same as the optionally substituted heterocyclic group included in the substituent group ( ⁇ ′).
  • R 5 or R 6 in the radical group represented by R 1 includes a hydrogen atom, an optionally substituted hydrocarbon group, and an optionally substituted heterocyclic group.
  • the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group are the same as the aforementioned optionally substituted hydrocarbon group and the optionally substituted heterocyclic group represented by R 1 . Things.
  • R 1 is the formula
  • X 1 is the same or different halogen atoms, halogen in 1 three optionally substituted alkyl group, C 2 _ 6 alkenyl, C 2 - 6 alkynyl group, Bruno, 1 in androgenic 3 pieces optionally substituted ( ⁇ _ 6 alkoxy groups, C 2 _ 6 alkenyl Okishi groups, C 2 _ 6 Arukiniruokishi group, halogen 1-3 amino optionally substituted with not good Ci 6 alkylthio groups, C 2 6 alkenylthio group, C 2 _ 6 alkynylthio, halogen 1-3 amino optionally substituted alkylsulfinyl group, C 2 - 6 ⁇ Luque Nils sulfinyl group, C 2 _ 6 alkynylsulfinyl group, a halogen 1-3 optionally substituted alkylsulfonyl group, C 2 _ 6 Arukenirusu Ruhoniru group,
  • X 1 may be linked together to form a methylenedioxy group, m represents an integer of 0 to 3, and D 1 represents an oxygen atom, a sulfur atom, or a formula NR dl (where R dl is a group represented by hydrogen atom, a Matahajito 6 ⁇ alkyl group.). Or a group represented by the formula
  • X 3 is a halogen atom, halogen 1-3 amino optionally substituted alkyl group, C 2 identical or different - 6 alkenyl, C 2 _ 6 alkynyl group from 1 to 3 in Ha androgenic Optionally substituted 6 alkoxy groups, 1 to 3 halogen-substituted C ⁇ 6 alkylthio groups, C alkylsulfinyl groups, alkylsulfonyl groups, C alkyl monocarbonyl groups, 6 alkoxy —Carbonyl, phenoxy, formamide, alkylcarbonylamino, Ci—ealkylsulfonyloxy, cyano, or nitro, n is an integer of 0 to 3, D 2 is oxygen, sulfur An atom or a group represented by the formula NR d 2 (wherein R d2 represents a hydrogen atom or an alkyl group). ] Is preferable.
  • R 1 is of the form
  • X 2 is the same or different and is a halogen atom, a C alkyl group or a C 1 -fluoro alkoxy group which may be substituted by 1 to 3 halogen atoms, and m ′ is an integer of 0 to 3 Indicates a number. Or a group represented by the formula
  • X 4 is the same or different and is a halogen atom, a C 6 alkyl group or a C 2 -e alkynyl group which may be substituted by 1 to 3 halogen atoms, and 1! 'Is an integer of 0 to 3 Is shown. Is preferably a group represented by
  • Y 1 represents a halogen atom, an alkyl group or — 6 alkoxy group optionally substituted with 1 to 3 halogen atoms
  • Y 2 and Y 3 represent 1 to 3 hydrogen atoms, halogen atoms, and halogen atoms, respectively. It represents an alkyl group or an alkoxy group which may be substituted. Or a group represented by the formula
  • Y 4 represents a halogen atom, an alkyl group or a C 2 _ 6 alkynyl group which may be substituted by 1 to 3 halogen atoms
  • Y 5 and Y 6 each represent a hydrogen atom, a halogen atom or a halogen atom. And represents an optionally substituted alkyl group.
  • Examples of the optionally substituted hydrocarbon group represented by R 2 and R 3 include the same as the aforementioned optionally substituted hydrocarbon group for R 1 .
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted eg, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, sec-pentyl, isopentyl, neopentyl, C ⁇ -e alkyl groups such as n-hexyl and isohexyl
  • a halogen atom eg, fluorine, chlorine, bromine, iodine
  • the number of the substituents is 1 to 4 (preferably 1 to 3).
  • Examples of the optionally substituted 3- to 8-membered cyclic hydrocarbon group which R 2 and R 3 may form together with adjacent carbon atoms include, for example, cyclopropane-1,1-diyl, cyclobutane-1 1 , 1 Jiiru, cyclohexane cyclopentane one 1, 1 Jiiru, cyclohexane - 1, 1-Jiiru, cycloheptane one 1, 1-Jiiru and cyclooctane - 1, 1 one Jiiru C, such as 3 - 8 cycloalkane Jiiru group Are used.
  • Examples of the substituent of the 3- to 8-membered cyclic hydrocarbon group formed by R 2 and R 3 taken together with the adjacent carbon atom include the same substituents as those of the heterocyclic group represented by R 1 above.
  • a halogen atom is used.
  • the number of substituents is 1-3.
  • R 2 and R 3 are each preferably an alkyl group which may be substituted by 1 to 3 halogen atoms.
  • C i _ 6 alkyl groups such as R 2 and R 3 are methyl or Echiru are preferred.
  • the optionally substituted hydrocarbon group and the optionally substituted hydrocarbon group represented by R 4 include the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group in R 1 above. And the same.
  • the optionally substituted hydrocarbon group and the optionally substituted hydrocarbon group represented by R 7 include the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group in R 1 above. And the same.
  • R 4 is (1) a halogen atom, each of which may be substituted with 1 to 3 halogen atoms — a 1 to 3 alkyl group and an alkoxy group which may be substituted with 1 to 3 halogen atoms (I) phenyl, (ii) naphthyl (eg, 1-naphthyl, 2-naphthyl) or (iii) phenyl (eg, 2-phenyl) group, 3 - thienyl group), (2) halogen 1-3 amino substitution which may be C alkoxy group, (3) optionally from 1 to 3 atoms substituted by halogen C 2 - 6 Arukeniruokishi group, (4) halogen 1-3 amino optionally substituted by C 2 _ 6 Arukiniruokishi group or (5) optionally phenoxy group which may be 1-3 amino substituted with halogen is preferred.
  • R 4 a halogen atom, each of which may be substituted with 1 to
  • X 5 represents a hydrogen atom, a halogen atom, 1-3 optionally substituted with halogen — 6 alkyl group or a C ⁇ e alkoxy group optionally substituted with 1 to 3 halogens .
  • Groups represented by, halogen 1-3 amino optionally substituted alkoxy group, halogen 1-3 amino optionally substituted C 2 6 alkenyl Ruokishi group, are 1-3 amino substituted by halogen which may phenoxy group force is 1-3 amino substituted with even better C 2 6 Arukiniruokishi group or halogen preferable.
  • Examples of the optionally substituted hydrocarbon group for R 8 include the same as the aforementioned optionally substituted hydrocarbon group for R 1 .
  • R 8 is preferably a hydrogen atom or an alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.).
  • the optionally substituted hydrocarbon group and the optionally substituted hydrocarbon group for R 9 include the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 1 described above. Similar ones can be mentioned.
  • Examples of the optionally substituted acyl group for R 9 include the same as the optionally substituted acyl group in the above substituent group ( ⁇ ′).
  • An alkoxy group which may be substituted by 1 to 3 alkoxy groups, (6) a cyano group, (7) a formyl group or (8) a hydroxy group is preferable.
  • Other hydroxy groups, CI- beta alkoxy or alkyl one Karuboniruo alkoxy which may be 1-3 atoms substituted with a group ( ⁇ _ 6 alkyl group is preferable.
  • R 1 G examples include the same as the aforementioned optionally substituted hydrocarbon group for R 1 .
  • R 1G is preferably a hydrogen atom or a 6- alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, etc.).
  • halogen atom in R 11 fluorine, chlorine, bromine, Ru and iodine.
  • the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 11 include the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 1 described above. Similar ones can be mentioned.
  • the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 16 are the same as the aforementioned optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 1 . Things.
  • Examples of the optionally substituted acyl group for R 16 include the same as the optionally substituted acyl group in the above substituent group ( ⁇ ′).
  • a halogen atom it may be 1-3 amino substituted by halogen - 6 alkyl group, ⁇ - 6 alkoxy group, (: I 6 alkylthio group, A C alkylsulfinyl group and a C alkylsulfonyl group are preferred.
  • R 1 2 fluorine, chlorine, bromine, Ru and iodine.
  • R] The optionally substituted hydrocarbon group for 2 include the same replacement which may also be a hydrocarbon group in R 1.
  • Examples of the halogen atom in Z include fluorine, chlorine, bromine, and iodine.
  • Examples of the optionally substituted hydrocarbon group for Z include the same as the aforementioned optionally substituted hydrocarbon group for R 1 .
  • Examples of the optionally substituted acyl group for Z include the same as the optionally substituted acyl group in the above substituent group ( ⁇ ′). Substituted in R 5 a and R 6 a the same as the hydrocarbon group which may be substituted in the R 1 can be mentioned as good Les hydrocarbon group.
  • Z represents a halogen atom, a cyano group, an alkyl group which may be substituted with 1 to 3 halogen atoms, a formula
  • R 17 is an alkyl group (eg, methyl, ethyl, n-propyl, iso) which may be substituted with 1 to 3 (1) nodogen (eg, fluorine, chlorine, bromine, iodine).
  • nodogen eg, fluorine, chlorine, bromine, iodine
  • R 17 x is a hydrogen atom or a halogen (eg, fluorine, chlorine, bromine, iodine), which may be substituted with 1 to 3 alkyl groups (eg, methyl, ethyl, n-propyl), Isopropyl, etc.). Or a group represented by the formula — C ⁇ NR 5b R 6b
  • R 5b and R 6b each may be substituted with 1 to 3 hydrogen atoms or halogens (eg, fluorine, chlorine, bromine, iodine) ( ⁇ -6 alkyl group (eg, methyl, ethyl , N-propyl, isopropyl, n-butyl, tert-butyl, etc.).
  • halogens eg, fluorine, chlorine, bromine, iodine
  • ⁇ -6 alkyl group eg, methyl, ethyl , N-propyl, isopropyl, n-butyl, tert-butyl, etc.
  • Preferred embodiments of the compound represented by the general formula (I) are represented by the following 1 and 2.
  • R 1 may be substituted by 1 to 3 halogen atoms, 6 alkyl groups, C 6 alkoxy groups, C 6 alkylthio groups, C 6 alkylsulfinyl groups or C ⁇ 6 alkylsulfonyl groups, respectively.
  • R 2 and R 3 each represent a 6- alkyl group
  • R 4 represents (1) 1 to 3 substituents substituted with a halogen or an alkyl group.
  • An optionally substituted phenyl group or (2) alkoxy group, — A— is a group of the formula
  • R 8 is a hydrogen atom or (: the I 6 alkyl group
  • R 9 is (i) a hydrogen atom, (ii) a halogen, hydroxy groups, C ⁇ - 6 alkoxy groups, C] - 6 alkylthio groups, C ⁇ - 6 alkylsulfinyl group, ( ⁇ 6 alkylsulfonyl group, (6 alkyl one local Poniruokishi group, hydroxy I amino group, Ji 1 is three substituted with Arukokishiimino group or alkyl one carbonyl O key Consequences amino group An optionally substituted C n alkyl group, (iii) a 6 cycloalkyl group, (iv) a C 6 alkenyl group, (V ) May be 1-3 substituted with an alkoxy group CI- 6 alkoxy group, (V i) formyl group, (vii) a Shiano group or (viii) a hydroxy group, R
  • R 12 represents a hydrogen atom.
  • R 1 is (1) halogen, —6 alkyl group, alkoxy group, C- 6 alkylthio group, C ⁇ 6 alkylsulfinyl group or C ⁇ 6 alkylsulfonyl group
  • R 9 is (1) hydrogen atom, (2) halo gen, hydroxy groups, C] -. 6 alkoxy groups, 6 alkylthio group, 6 Al Kirusurufiniru Group, alkylsulfonyl group, 6- alkyl-carboxyloxy group, hydroxyimino group, 6 -alkoxyimino group or 6- alkyl-carbonyloxymino group which may be substituted by 1 to 3 C alkyl groups , (3) C 3 - 6 cycloalkyl group, (4) C 2 - 6 alkenyl group, (5) Ji Bok 6 alkoxy groups 1-3 amino substituted 6 may be alkoxy groups, (6) formyl group, (7) a Shiano group or (8) a hydroxy group, a R 1Q is a hydrogen atom or an alkyl group, R 11 is a hydrogen atom, alkyl group, an alkylthio group,
  • R 12 is a hydrogen atom
  • Z is (1) an alkoxy-carbonyl group optionally substituted with 1 to 3 halogen atoms, and (2) 1 to 3 halogen atoms may be substituted.
  • ⁇ 9- aralkyloxy-carbonyl group (3) a compound showing a ⁇ 6 alkyl monocarbonyl group or (4) a mono- or di-(. 6 ) -alkyl rubamoyl group or a salt thereof.
  • the compound represented by the general formula (I) can be divided into the following formulas (Ia), (Ib), (Ic) and (Id) by a group represented by 1A-.
  • X 2 a are the same or different and are each substituted with 13 halogen atoms or halogens.
  • X 4a may be the same or different halogen atoms, halogen in 1-3 amino optionally substituted alkyl group or C 2 - 6 alkynyl group, eta '' is an integer of 0 to 3.
  • R 4a is substituted with 1 to 3 identical or different, halogen atoms, 1 to 3 halogen optionally substituted C 6 alkyl groups, or 1 to 3 halogen optionally substituted alkoxy groups (I) a phenyl group, (H) a naphthyl group (eg, a 1-naphthyl group, 2-naphthyl group) or (iii) a phenyl group (eg, a 2-phenyl group, a 3-phenyl group) or a compound of the formula
  • R 7a is an alkyl group optionally substituted with 1 to 3 halogens, a C 2 _ 6 alkenyl group optionally substituted with 1 to 3 halogens, 1 to 3 substituted with halogens which may be C 2 - 6 alkynyl group or the same or different halogen and are 1-3 amino substituted with emissions atoms shows even better phenylene Le group), a group represented by.
  • the R 8 a hydrogen atom or a C i _ 6 alkyl group
  • R 9a is a hydrogen atom or a hydroxy group, C - 6 alkoxy or 6 alkynyl Luca Lupo alkenyl O dimethylvinylsiloxy groups at 1 three optionally substituted C I 6 alkyl group
  • R 17a is 1 in (i) halogen three optionally substituted alkyl group or (ii) a halogen atom, with 1 was three optionally substituted C Bok 6 alkyl groups or halogen may be 1 to 3 substituted with halogen alkoxy
  • R 1Ga represents a hydrogen atom or a 6- alkyl group, and the other symbols have the same meanings as described above.
  • the compound represented by this is mentioned.
  • R lla is a hydrogen atom, a halogen substituted by 1 to 3 Ji may Bok 6 Al kill groups, C WINCH 6 alkoxy group, Bok 6 alkylthio group, CI_ 6 alkylsulfide alkenyl group or a C ⁇
  • the 6- alkylsulfonyl group and other symbols are as defined above. ] The compound represented by this is mentioned.
  • the compound (I) of the present invention can form a basic salt in which an acid group such as a sulfo group or a carboxyl group in a substituted moiety in the molecule is an agricultural chemical acceptable with an inorganic base, an organic base, or the like; A basic nitrogen atom in the molecule and a basic group such as an amino group in the substitution can form an acid addition salt that is agriculturally acceptable with an inorganic acid or an organic acid.
  • the inorganic base salt of the compound (I) include salts with an alkali metal (eg, sodium, potassium, etc.), an alkaline earth metal (eg, calcium, etc.), ammonia, etc., and an organic base of the compound (I).
  • salts with dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine, collidine and the like are used.
  • Examples of the inorganic acid addition salt of compound (I) include salts with hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, and the like.
  • Examples of the organic acid addition salt of compound (I) include p-toluenesulfonic acid , methanesulfonic acid, formic acid, c present invention salts with Torifuruoro acetate is used wherein
  • R 9p is a hydrogen atom, an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, L is a leaving group, and other symbols are as defined above.
  • the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 9 P are the same as the optionally substituted hydrocarbon group and the optionally substituted heterocyclic group for R 9 described above.
  • the R 9p 0) hydrogen atom, (2) (i) halogen, (ii) hydroxy group, (iii) ⁇ - 6 alkoxy group, (iv) C 1 _ 6 alkylthio groups, Alkylsulfinyl group, (VOC ⁇ e alkylsulfonyl group, (viOC ⁇ 6 alkyl - Under wherein, R 14 is as defined above.]
  • Carbonyl O alkoxy group, or (viii) formula N-OR 1 4 1 to 3 substituted with the groups shown Which may C ⁇ 6 alkyl group, (3) C 3 _ 6 cycloalkyl group or (4) C 2 _ 6 alkenyl Le group.
  • a hydrogen atom, (2) halogen, hydroxy, or C -e alkoxy group (: Preparative 6 alkylthio group with 1 to 3 amino optionally substituted ⁇ alkyl group or (3) C 3 - 6 Cycloalkyl groups are preferred.
  • the leaving group represented by L includes a halogen atom (eg, fluorine, chlorine, bromine, iodine), a hydroxy group, -OS (O) C 1 or a formula — OS ( ⁇ ) 2 R 18 (wherein R 18 Represents a hydrocarbon group which may be substituted, and includes a group represented by:
  • optionally substituted hydrocarbon group for R 18 examples include the same as the aforementioned optionally substituted hydrocarbon group for R 1 , preferably methyl, trifluoromethyl, 4-methylphenyl and the like.
  • L is particularly preferably a halogen atom (eg, fluorine, chlorine, bromine, iodine), a hydroxy group, one OS (O) C 1 or a trifluoromethylsulfonyloxy group.
  • a halogen atom eg, fluorine, chlorine, bromine, iodine
  • L 1 is a halogen atom (eg, fluorine, chlorine, bromine, iodine), a hydroxy group, —OS (O) C 1 or a formula — OS (0) 2 R 18 (where R 18 is as defined above) And the other symbols have the same meanings as described above. ] And expression
  • salts of the compounds (II-a-1), (II-b-1), ( ⁇ -a-lx) and ( ⁇ -b-lx) the same as the salts of the compound (I) described above are used.
  • the present invention uses the formula
  • keto and enol tautomers can also exist as a tautomer. Each can also be present as a mixture of said keto and enol tautomers.
  • salts of the compounds (II-a-3) and (II-b-3) those similar to the salts of the compound (I) described above are used.
  • the present invention uses the formula
  • R lx represents a hydrogen atom, a benzyl group or an iert-butyl group, and the other symbols have the same meanings as described above. Or a salt thereof, and a compound represented by the formula:
  • a compound represented by or a t compounds relates to their salts ( ⁇ - a) or of a salt thereof, a compound group R lx is a hydrogen atom ( ⁇ - a - 1) or a salt thereof, compound (I- a-1) or a salt thereof, wherein the group R 1 is a compound represented by the formula CONR5R 6 (the symbols in the formula are as defined above.)
  • a compound in which the group R lx represents a benzyl group ( ⁇ -b-2) or a salt thereof is a synthetic intermediate of compound (Il′-b-1) or a salt thereof.
  • the compound ( ⁇ -a) or a salt thereof the compound ( ⁇ -a-3) or a salt thereof in which the group R lx represents a tert-butyl group is a compound (I-a-lr) or a salt thereof or Intermediate for the synthesis of compound (I-C-r) or a salt thereof.
  • the salt thereof is a compound (Ib-lr) or a salt thereof or a synthetic intermediate of the compound (I-d-r) or a salt thereof.
  • Salts of compounds ( ⁇ -al), ( ⁇ -a-2), (II'-a-3), (II'-bl), (II'-b-2) and ( ⁇ '-b-3) The same as the above-mentioned salt of compound (I) can be used. It is.
  • the compounds ( ⁇ ′-a-1), ( ⁇ ′-a-2), (II′-a-3), (II′-bl), (II) '-b-2) and (II'-b-3) may be collectively referred to as the present compound (II).
  • the compound represented by the above general formula ( ⁇ ) or ( ⁇ ) has one or more asymmetric centers
  • the compound represented by the general formula (II) or ( ⁇ ') has two or more asymmetric centers.
  • enantiomers eg, enantiomers, diastereomers, etc.
  • the general formula (II) or (II) includes all of these stereoisomers and a mixture of any two or more of them. Have been.
  • the compound represented by the general formula ( ⁇ ) or ( ⁇ ) may have two or more geometrical isomerisms.
  • Isomers eg, ⁇ / ⁇ or trans / cis isomers, S-trans / S-cis isomers, etc.
  • these are not represented by general formula (II) or ( ⁇ '). It includes all geometric isomers and mixtures of any two or more of them.
  • the compound (I) of the present invention or a salt thereof is useful as a herbicide having excellent safety, and has a very low dose and a wide range of weeds, for example, Thai fluegrass, Himeyuinubiye, Yumagayari, Kogomegayari, Hyderico, Matsubai, Inuho Yurui, Evening Iwanamai, Mizugayari, Krogwai, Kozukiyara, Shizi, Konagi, Azena, Abnome, Kikashidasa, Himemisohagi, Mizohakobe, Chiyouji Yude, Perika Mika, Hera Komoka, Hera Komoka , Azetogarashi, Takasa Blow, Ibokusa, Kishusuzumenohye, Ezonosayanu Ridasa, etc.
  • weeds for example, Thai fluegrass, Himeyuinubiye, Yumagayari, Kogomegayari, Hyderico, Matsubai
  • Compound (I) or its salt is excellent between crops and various weeds It has a selective herbicidal effect, has low toxicity to mammals and seafood, does not pollute the environment, and is extremely safe to use as a herbicide for paddy fields, fields, lawns, orchards or non-agricultural land be able to. Among them, it is suitable as a herbicide used in paddy fields.
  • the compound (I) of the present invention or a salt thereof is used as a herbicide
  • one or more kinds of compounds (I) or a salt thereof can be used in the form of a general agricultural chemical.
  • These preparations may contain an emulsifier, a dispersant, a spreading agent, a penetrant, a wetting agent, a binder, a thickener and the like, if necessary, and can be prepared by a method known per se.
  • liquid carrier examples include water, alcohols (eg, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (eg, acetone, methylethyl) Ketones), ethers (eg, dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (eg, kerosene, kerosene, fuel oil, machinery) Oils), aromatic hydrocarbons (eg, benzene, toluene, xylene, solvent naphtha, methyl naphthalene, etc.), halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, etc.), acid amides ( For example, dimethylformamide, Ruase Bok amides), esters (e.g., dimethylformamide
  • solid carriers examples include, for example, vegetable powders (eg, soybean flour, evening coconut flour, flour, wood flour, etc.) and mineral powders (eg, kaolin, bentonite, acid clay, clay, etc.) Clays, talc powder, talc powder such as talc powder, diatomaceous earth, silica powder such as mica powder, etc.), alumina, sulfur powder, activated carbon, sugars (eg, lactose, glucose, etc.), inorganic Salts (eg, calcium carbonate, sodium bicarbonate, etc.), hollow glass bodies (natural glass materials that are fired and air bubbles are contained therein), and the like are used. They are examples of vegetable powders (eg, soybean flour, evening coconut flour, flour, wood flour, etc.) and mineral powders (eg, kaolin, bentonite, acid clay, clay, etc.) Clays, talc powder, talc powder such as talc powder, diatomaceous earth, silica powder such as mica powder, etc.),
  • liquid carrier or solid carrier can be used usually in an amount of about 1-99% by weight, preferably about 10-99% by weight, based on the whole preparation.
  • a surfactant is used as required.
  • these surfactants include polyoxyethylene alkyl ether (eg, Sanyo Chemical Industries, Ltd., Emulmin 110), polyoxyethylene alkyl aryl ether (eg, Sanyo Chemical Co., Ltd.) Nonipol 85, Nonipol 100, Nonipol 160, etc.), polyoxyethylene lanolin alcohol, polyoxyethylene alkylphenol phenol formalin condensate, polyoxyethylene sorbitan fatty acid ester (eg, manufactured by Kao Corporation), Tween 20, Tween 80, Daiichi Kogyo Seiyaku Co., Ltd., Sorgen TW-20, Sorgen TW-80, etc.), polyoxyethylene glyceryl monofatty acid ester, polyoxypropylene glycol monofatty acid ester, poly Oxyethylene sorbitol fatty acid ester, polyoxyethylene Pe
  • Higher fatty acid sodium salt eg, sodium palmitate, etc.
  • ether carboxylate sodium salt eg, polyoxyethylene lauryl ether carboxylate, etc.
  • amino acid condensate of higher fatty acid eg, lauguchi sarcosine sodium
  • N-lauroyl glutamate e.g.
  • higher alkyl sulfonates eg, higher fatty acid ester sulfonates (eg, lauric acid S) Tersulfonates, etc.
  • ligninsulfonates eg, sodium ligninsulfonate
  • alkylsulfosuccinates eg, sodium dimethylhepsulfosuccinate, sodium dioctylsulfosuccinate, dinonylsulfosuccinate
  • higher fatty acid amide sulfonates eg, oleic acid amide sulfonates, etc.
  • binder examples include dextrin (eg, Nissei Chemical Co., Ltd., dextrin ND-S, etc.), sodium salt of carboxymethylcellulose (eg, Daiichi Kogyo Yakuhin Co., Ltd., Cellogen 5A, Cellogen 6A, cellogen 7A, cellogen PR, etc.), polycarboxylic acid polymer compound (eg, manufactured by Sanyo Chemical Industries, Ltd., Toxanone GR—30, Toxanone GR—31A, Toxanone GR—50L, Toxanone GR—60 L; manufactured by Kao Corporation, Boys 530, Boys 532 A, etc.), polyvinylpyrrolidone, polyvinyl alcohol, sodium ligninsulfonate, calcium ligninsulfonate, sodium polyacrylate, Arabic Gum, sodium alginate, glucose, sucrose, mannitol, sorbitol and the like are used.
  • the binder can be used usually in an amount of about 0 to 20% by
  • the thickener examples include bentonite minerals (eg, high-purity sodium montmoly) ), Polyacrylic acid and its derivatives, sodium salts of carboxymethylcellulose (eg, Daiichi Kogyo Seiyaku Co., Ltd., cellogen 5A, cellogen 6A, cellogen 7A, cellogen PR, etc.), white Ripbons, natural saccharide derivatives (eg, xanthan gum, guar gum, etc.) are used.
  • the thickener is usually used in an amount of about 0.01 to 10% by weight based on the whole preparation.
  • the preparation form for using the compound (I) of the present invention or a salt thereof as a herbicide granules and flowables are preferable, and among the granules, water-floating granules and aqueous among the flowables are preferable. Suspensions are particularly preferred.
  • the present invention also relates to water-suspendable granules and aqueous suspensions containing the compound (I) of the present invention or a salt thereof.
  • a powder base having a specific gravity of 1 or less is usually used as a carrier.
  • these powder bases those having a particle diameter of 600 m or less, preferably 300 m or less are preferable.
  • the above-mentioned glass hollow body that is, natural vitreous material is used. Is fired to have one or more independent bubbles in it, for example, perlite made of perlite or obsidian, shirasu balloon made of shirasu, bamikirite made of vermiculite, etc. And fine hollow spherical spheres obtained by sintering with an aminosilicate system.
  • higher fatty acids eg, stearic acid, palmitic acid, etc.
  • higher alcohols eg, stearyl alcohol, etc.
  • paraffin wax polyethylene powder (eg, Sanyo Chemical Industries Co., Ltd., Sunwax 131-P, Sunwax 151-P, Sunpax 161-P, Sunwax 171-P, etc., polypropylene powder (eg, Sanyo Chemical Industries, Ltd.) Products, viscol 330-P, viscol 550-P, picocol 660-P, etc.). It is preferably a hollow glass body, particularly preferably pearlite.
  • the powder base having a specific gravity of 1 or less can be used usually in an amount of about 10 to 90% by weight, preferably about 30 to 90% by weight, based on the whole preparation.
  • a surfactant having a large surface tension lowering ability is generally used.
  • these surfactants those capable of lowering the surface tension of water to 35 dyne Z cm or less at 25 ° C. are used. Examples thereof include alkyl benzene sulfonate, polyoxyethylene alkyl ether, and polyoxyethylene.
  • Renalkyl phenyl ether, polyoxyethylene alkyl phenyl ether sulfate, alkyl sulfosuccinate eg, manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd., Neocol YS-K, Neocol SW-CE; Takemoto Yushi Co., Ltd., New Calgen ⁇ -70G; Toho Chemical Co., Ltd., Airroll CT-11; Sanyo Chemical Industries, Ltd., Sanmorin ⁇ -70, etc., acetylene glycol (eg, Air's products, Surfynol 104, Surfinol 104 ⁇ , Surfinol 104 ⁇ , Surfinol 104 ⁇ , Surfinol 104 ⁇ , Surfinol TG, Surfinol TG—E, Surfinol PC, Surfinol 61, Safinol 82, Surfinol 40, Surfinol Finol 465; Nissin Chemical Co., Ltd., Ol
  • Alone, or two or more kinds may be mixed at an optional ratio if necessary.
  • alkyl sulfosuccinate and acetylenic alcohol-based surfactants are particularly preferred.
  • the surfactant having a large interfacial tension lowering ability can be used usually in an amount of about 0.1 to 20% by weight, preferably about 1 to 10% by weight, based on the whole preparation.
  • a binder In the water-floating granules of the present invention, a binder is usually used. These binders include the above-mentioned binders, and one or more (preferably 1 to 3) of these binders are used. Preferred are carboxymethylcellulose or a salt thereof (eg, a sodium salt) and a polycarboxylic acid polymer compound.
  • the binder can be used usually in an amount of about 0.1 to 20% by weight, preferably about 1 to 20% by weight, based on the whole preparation.
  • the water-floating granules of the present invention can contain an organic solvent as needed.
  • organic solvents include, for example, phthalic acid esters (eg, dimethyl phthalate, di-octyl phthalate, di- 20 alkyl phthalate such as ditridecyl phthalate), aliphatic monocarboxylic acid esters (eg, Esters such as ethyl palmitate, methyl laurate, etc., aliphatic dicarboxylic acid esters (eg, octyl succinate), xylene, ethylbenzene, octadecyl benzene, sorbesse series (eg, Exxon Chemical, Solbesso 100, Solbesso 150, Solbesso 200, etc.), Methylnaphthalene (eg, Kawasaki Kasei Kogyo Co., Ltd., Wakazoiru, etc.), dodecylnaphthalen
  • a surfactant may be further added as a wetting agent, emulsifier or dispersant.
  • these surfactants include the above-mentioned surfactants, preferably a polyoxyethylene polyoxypropylene block polymer (eg, Newpol PE-68, Newpol PE-1 manufactured by Sanyo Chemical Industries, Ltd.) 6 4) etc. are used.
  • the surfactant can be used usually in an amount of about 0.1 to 30% by weight, preferably about 0.1 to 20% by weight, based on the whole preparation.
  • an appropriate amount of a bulking agent may be added as long as the apparent specific gravity of the granules is 1 or less.
  • the extender preferably promotes or does not hinder the dispersion of the active ingredient in water, and is preferably water-soluble or water-dispersible.
  • water-soluble fertilizers eg, urea, ammonium sulfate, ammonium chloride, potassium chloride, etc.
  • water-soluble sugars eg, lactose, glucose, etc.
  • inorganic salts eg, calcium carbonate, sodium bicarbonate, etc.
  • Fine powder eg, bentonite, ziglite, acid clay, diatomaceous earth, etc.
  • the compounding amount of the extender is usually 50% by weight or less based on the whole preparation.
  • the water-floating granules of the present invention include the compound (I) of the present invention or a salt thereof, if necessary, a powder base having a specific gravity of 1 or less, a surfactant, a binder, an organic solvent, and other herbicidal activities.
  • Ingredients and, if desired, other pesticidal active ingredients, extenders and the like are mixed and kneaded to produce.
  • the above components are charged into a commonly used mixer, for example, a repump blender V-type mixer, mixed well, then transferred to a mixer and added with water.
  • the mixture is granulated by an extrusion granulator to obtain granules having a particle size of 5 to 5 mm.
  • the water-floating granules of the present invention produced in this manner have good diffusibility on the water surface, and when sprayed on a paddy field or the like, the pesticidal active ingredient is uniformly dispersed on the entire water surface. There is virtually no phytotoxicity to cultivated crops, and there is virtually no harm to animals or seafood during or after application, and it can be used safely.
  • the water-floating granules of the present invention may be packaged in a water-soluble film in a unit of 20 to 200 g for easy application.
  • the water-soluble film include polyvinyl alcohol, carboxymethyl cellulose, starch, gelatin, polyvinylpyrrolidone, polyacrylic acid and its salts, starch-based polysaccharides (eg, Hayashibara Shoji, Pullulan, etc.), thermoplastic water-soluble polymers (for example, Daiichi Kogyo Seiyaku Co., Ltd., Pogen etc.), and one or a mixture of two or more of them can be used. Further, a mixture of wood pulp may be used. In either case, it is better to select a film that dissolves or disperses rapidly in water.
  • the water-floating granules according to the present invention do not sink when dropped on the surface of water because of their apparent specific gravity of 1 or less, but contain a surfactant having a large interfacial tension-reducing ability, so that water is quickly dispersed in the granules.
  • the surfactant begins to dissolve, the surface tension of the water around the particles decreases, the particles are pulled outward from the drop point on the water surface, and the gap between the particles spreads and begins to collapse.
  • the surfactant is uniformly contained inside the water-floating granules of the present invention, the particles spread and collapse on the water surface until they become primary particles (minimum units constituting non-agglomerated particles).
  • the pesticide active components having a specific gravity of 1 or more disperse in water, and finally, only the powder base having a specific gravity of 1 or less remains on the water surface.
  • the pesticide active ingredient is evenly distributed throughout the paddy field. Such spreading, disintegration, and dispersion of the water-floating granules occur very instantly, so there is no risk of the pesticide active ingredient being biased in the paddy field due to the effect of the wind at the time of spraying, or of phytotoxicity.
  • a surfactant may be added to the aqueous suspension of the present invention as a wetting agent or a dispersing agent.
  • These surfactants include the above-mentioned surfactants, and are preferably alkylsulfosuccinates. (Eg, sodium octyl sulfosuccinate (eg, Neocol YS-K, etc., manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.), etc.), polyoxyethylene alkyl Kilaryl phosphoric acid ester salts (eg, Agrizol FL-2017, manufactured by Kao Corporation) and the like are used.
  • the surfactant can be used usually in an amount of about 0.1 to 20% by weight, preferably about 0.1 to 10% by weight, based on the whole preparation.
  • An antifreezing agent, an antifoaming agent, a preservative, and a thickener may be added to the aqueous suspension of the present invention as needed.
  • the antifreeze include ethylene glycol, propylene glycol and the like, which can be used usually in an amount of about 1 to 20% by weight based on the whole preparation.
  • Antifoaming agents include, for example, Antifoam E-20 (manufactured by Kao Corporation) and the like, which can be used usually in an amount of about 0.05 to 0.5% by weight based on the whole preparation.
  • the preservative for example, butyl p-hydroxybenzoate, sorbic acid, potassium sorbate and the like can be mentioned, and usually about 0.05 to 3% by weight based on the whole preparation can be used.
  • the thickener include the above-mentioned thickeners, and preferably, high-purity sodium montmorillonite (eg, Knipine F, manufactured by Kunimine Industry Co., Ltd.) is used.
  • the thickener can usually be used in an amount of about 0.01 to 10% by weight based on the whole preparation.
  • the aqueous suspension of the present invention may be prepared according to a method known per se or a method analogous thereto, the compound (I) of the present invention or a salt thereof, if necessary, a surfactant and other herbicidally active ingredients, and if desired, other agricultural chemicals. It can be produced by dissolving or suspending active ingredients, antifreezing agents, defoamers, preservatives, thickeners, etc. in water. For example, all the components to be used are stirred and mixed by a stirrer, and then finely pulverized and dispersed by a wet pulverizer such as Dynomill or Microfluidizer (Production Method 1), or an active ingredient such as a herbicide or the like.
  • a wet pulverizer such as Dynomill or Microfluidizer (Production Method 1)
  • the active ingredient of the aqueous suspension of the present invention is in the form of fine particles in the preparation and is dispersed in water. When other powder components are used, they are similarly dispersed in water.
  • the average particle size of the fine particles is about 10 m or less, preferably 0.1-5 m.
  • the aqueous suspension of the present invention produced in this way has good diffusibility in water, and the pesticidal active ingredient is uniformly dispersed in water. In addition, there is virtually no harm during or after application to animals and seafood, and it can be used safely.
  • the content of the compound (I) of the present invention or a salt thereof in a preparation is preferably about 1 to 90% by weight in emulsions, wettable powders, wettable granules, liquid preparations, aqueous solvents, flowable preparations and the like.
  • oils, powders, DL-type powders, etc. and about 0.05 to 10% by weight for fine granules, fine granules F, fine granules F, granules, etc. % Is appropriate. These concentrations may be appropriately changed depending on the purpose of use.
  • Emulsions, wettable powders, condensate wettable powders, liquid preparations, aqueous solvents, flowable preparations, etc. are appropriately diluted with water, etc. before use (for example, about 100 to 100,000 times) and sprayed. You can also.
  • the method of application can be the same as the method of applying a general pesticide, and examples include aerial application, soil application, foliage application, nursery box application, lateral application, seed treatment, and the like.
  • aerial application soil application, foliage application, nursery box application, lateral application, seed treatment, and the like.
  • foliage application foliage application
  • nursery box application lateral application
  • seed treatment seed treatment
  • the like seed treatment
  • when applied to a paddy field it is applied by a method known per se (eg, hand spreading, power spraying, etc.).
  • the amount to be used varies depending on the application scene, application time, application method, target grass species, cultivated crops, and the like.
  • (I) or its salt) about 0.05 to 50 g per 1 are of paddy field, preferably 0.1 to about 0 g of L, about 0.05 to 50 g per 1 are of upland field, preferably It is about 0.1 to 10 g.
  • the compound (I) or a salt thereof of the present invention is suitably used for paddy field weeds, as a soil treatment before emergence, or as a foliage / soil treatment agent.
  • a herbicide containing the compound (I) or a salt thereof of the present invention can be used safely without developing phytotoxicity immediately after planting or 1 to 3 weeks after planting, and the effect is maintained for a long time.
  • the herbicide containing the compound (I) of the present invention or a salt thereof may be, if necessary, one or more (preferably 1 to 3) other herbicides, plant growth regulators, fungicides, It can be applied simultaneously with insecticides, acaricides, nematicides, etc.
  • One or more (preferably 1 to 3) other herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematicides, etc. are blended and mixed. You can also.
  • herbicides include, for example, (1) sulfonylurea herbicides [bensul furon-methyl], pyrazosul furon-ethyl> imazosul furon ), Sul fosul iuron, cinosul furon, azimsul furon ), Metsulfuron-methyl, halosulfuron-methyl, ethoxysul furon, cyclosulfamuron, etc.), (2) pyrazole herbicide [birazolate ( pyrazolate), pyrazoxyfen, benzofenap, etc.), (3) potato herbicide [benthiocarb], molinet (mol inate), esprocarb, esprocarb, pyributicarb), dimepiperate, swep, etc.), (4) chloroacetanilide herbicides [butachlor, pretilachlor, tenylchlor, etc.], (5) diphenyl ether
  • plant growth regulators active ingredients for regulating plant growth
  • examples of plant growth regulators include, for example, hymexazol> paclobutrazol, paclobutrazol, niconazol-P (unicotulole-P), and inabenfide prohexadione calcium (inabenfide). prohex adione-calcium).
  • fungicides include (1) polyhaloalkylthio fungicides [captan] etc., (2) organophosphorus fungicides [IBP EDDP, tolclofos-methyl] ), Etc.), (3) Benzimidazole fungicides [benomil, carbendazim, thiophanate-methyl, etc.], (4) Carboxamide fungicides [mepronil, flutranil (Flutolanil), thifluzamide (thi fluzamid), furametopyru (furaetpyr), techoku phthalam (teclof thalam), pencyclon (pencycuron), carile propamide (can> ropainid), diclosymet (diclocymet), etc., (5) Fungicides [metalaxyl etc.], (6) azolic fungicides [triflumizole, ipconazole, pefurazole] azoate), prochloraz, etc.
  • insecticides include (1) organophosphorus insecticides [fenthion, fenitrothion, pirimiphos-methyl, diazinon, quinalphos] , Isoxathion, pyridafenthion, chlorpyrifos-methyl, vamidothion, malathion, phenthoate, dimethoate, dimethoate disulfoton), monocrotophos, tetrachlorvinphos, chlorfenvinphos, chlorfenvinphos, propaphos, acephate, trichlorfon, EPN, pirak (Pyraclofos), etc.), (2) Carbamate insecticides [cararyl, carbaryl, Tolcarb (metolcarb), isoprocarb (isoprocarb), B PMC, propoxur (propoxur), XMC, carbofuran (carbofuran), carbosulfan (car
  • acaricides active miticide components
  • examples of acaricides include hexthithiaz ox, pyridabeiu, fenpyroximate, tebufenpyrad, chlorfenapyr, etoxazole. Pyrimidifen and the like.
  • nematicide nematicidal active ingredient
  • examples of the nematicide include fosthiazate and the like.
  • pesticidal active ingredients eg, herbicidal active ingredients, plant growth regulating active ingredients, bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, etc.
  • herbicidal active ingredients eg, herbicidal active ingredients, plant growth regulating active ingredients, bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, etc.
  • plant growth regulating active ingredients e.g., bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, etc.
  • bactericidal active ingredients e.g., bactericidal active ingredients, insecticidal active ingredients, acaricidal active ingredients, nematicidal active ingredients, etc.
  • 0.1 to 20% by weight preferably about 0.1 to 10% by weight can be used.
  • the pesticidal composition containing the compound (I) or a salt thereof of the present invention is used in combination with another pesticidal active ingredient as described above, a formulation containing the other pesticidal active ingredient as a compound (I) or a salt thereof
  • the active ingredients can be mixed, blended and used in the same preparation, and the active ingredients can be formulated separately and used simultaneously or separately at different times.
  • the agrochemical composition containing the compound (I) or a salt thereof and other herbicidal active ingredients it is preferable to use the above-mentioned water-suspendable granules and aqueous suspensions.
  • imazosulfone is particularly preferably used.
  • Herbicides containing the compound (I) of the present invention or a salt thereof further include a synergist (eg, piperonyl butoxide), an attractant (eg, eugenol), and the like.
  • Repellents eg, creosote, etc.
  • pigments eg, Food Blue No. 1, etc.
  • fertilizers eg, urea, etc.
  • the compound (I) of the present invention or a salt thereof is a novel compound, but can be produced according to a method known per se or a method analogous thereto.
  • the compound (I) or a salt thereof is produced according to the following reaction scheme 1.
  • the compound (a-1), (Ic), (I-b-1), (I-d) or a salt thereof is produced according to the following reaction scheme 1.
  • the compound (II-a-1), (IIb-1) or a salt thereof is subjected to an elimination reaction to eliminate the leaving group L and a hydrogen atom on an adjacent carbon atom.
  • the compound (I-a-1) which is formed by elimination of the hydrogen atom on the carbon atom to which the group R 8 is bonded and the group L, is usually used as the starting compound (I-a-1).
  • the group R 9 p has a hydrogen atom involved in the elimination reaction, that is, when the group R 9 p corresponds to the group R 11 R 12 CH, the compound formed by elimination of this hydrogen atom and the group L (I-c) may also be obtained.
  • the compound (I Ib-1) when used as a starting compound, the compound (I-b-1) formed by elimination of a hydrogen atom on the carbon atom to which the group R 1 Q is bonded and the group L is usually obtained.
  • the group R 9 p corresponds to the group R 11 R 12 CH, the compound (Id) formed by the elimination of the hydrogen atom and the group L on this group may also be obtained. is there.
  • Suitable solvents include, for example, aromatic hydrocarbons such as benzene and toluene, dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane.
  • Halogenated hydrocarbons such as benzene, benzene, 0-dichlorobenzene, etc., tetrahydrofuran (hereinafter abbreviated as THF), ethers such as dioxane, nitriles such as acetonitrile, acetone, methylethyl ketone, etc.
  • Ketones esters such as ethyl acetate, alcohols such as methanol and ethanol, N, N-dimethylformamide (hereinafter abbreviated as DMF), N, N-dimethylacetamide (hereinafter DMA)
  • DMF N, N-dimethylformamide
  • DMA N, N-dimethylacetamide
  • DMSO dimethylsulfoxide
  • a mixed solvent thereof is used.
  • a base can be added to accelerate the reaction.
  • the base used in this reaction include, for example, triethylamine, tripropylamine, ethyldiisopropylamine, pyridine, collidine, lutidine, 1,8-diazabicyclo [5.4.0] -7-dendecene (hereinafter, referred to as “triethylamine”).
  • DBU DBU
  • organic bases such as 1,4-diazabicyclo [2.2.2] octane, 1,5-diazabicyclo [4.3.0] non-5-ene, sodium hydride, and hydroxide
  • Inorganic bases such as sodium, hydroxide hydroxide, sodium carbonate and potassium carbonate, metal alkoxides such as sodium methoxide, sodium methoxide and potassium tert-butoxide are used.
  • the base is generally used in the amount of 1 to 20 mol equivalent based on compound (II-a-1) or ( ⁇ -b-1).
  • an organic base such as pyridine can be used as a solvent.
  • a reactant such as a combination of thionyl chloride, oxychlorinated salt, triphenylphosphine carbon tetrachloride, and trifluoromethanesulfonic anhydride is usually used in an amount of 1 molar equivalent or more (preferably 1 to 35 molar equivalents).
  • This elimination reaction can be carried out by generating a compound having a substituent having a higher elimination property such as a group having a substituent.
  • the reaction temperature of this reaction is usually about 120-150 ° C, preferably about 0-10 O :. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound having a group represented by the formula or a salt thereof is a compound having a hydroxy group as a group (II-a-D), (II-bD or a salt thereof)
  • the compound (II-a- ⁇ ), (II-b-1 ′) or a salt thereof can be easily produced according to a known method or a method analogous thereto.
  • a compound having a group represented by the following formula: OS (O) 2 R 18 (where R 18 is as defined above) or a salt thereof is once isolated and subjected to the reaction shown in Reaction Scheme 1. It is also possible to carry out the reaction of reaction scheme 1 in the reaction mixture in which they are formed without isolation.
  • the compounds (II-a- ⁇ ), (II-b- ⁇ ) or salts thereof can be produced according to the following reaction scheme 2.
  • the salts of the following compounds (--a-1), (III-b-1), (IV-a-1), (IV-b-1) and (V) are the above-mentioned compounds (I) The same ones as the above salts are used.
  • Examples of the leaving group represented by L 2 include a halogen atom (eg, fluorine, chlorine, bromine, iodine, etc.) or a general formula
  • Q 4 is an alkyl group (eg, methyl, ethyl, n-propyl, isopropyl, n-butyl) which may be substituted with 1 to 5 halogen atoms (eg, fluorine, chlorine, bromine, iodine).
  • alkyl group eg, methyl, ethyl, n-propyl, isopropyl, n-butyl
  • halogen atoms eg, fluorine, chlorine, bromine, iodine
  • halogen eg, fluorine, chlorine, bromine, iodine
  • C ⁇ 6 alkyl group eg, methyl, ethyl, n-propyl, isopropyl, n-butyl
  • C 6 _ 14 7 aryl group e.g., phenyl
  • C 7 19 Ararukiru group e.g., Phenyl such as benzyl 1 ⁇ alkyl.
  • acetyloxy, isobutyloxycarponyloxy, etc. and the like.
  • a halogen atom is preferred, and chlorine is particularly preferred.
  • compound (IV) of compound (IV-a-1), (IV-b-1) or a salt thereof is usually added in an amount of 1 molar equivalent or more (preferably 1 to 2 molar equivalents) or Reacting with a salt to form compound (III-a-1), (III-b-1) or a salt thereof, and then, as a second step, compound ( ⁇ -al), (III-b-1) or The salts are reacted with a base to effect a ring closure reaction.
  • Compound ( ⁇ -a-1), (III-b-1) or a salt thereof is a novel compound.
  • This reaction is a two-step reaction, and is formed in the first step by reacting compound (IV-a-1), (IV-b-1) or a salt thereof with compound (V) or a salt thereof. After isolating the compound (III-a-1), (III-b-1) or a salt thereof, it is possible to carry out a ring closure reaction by the action of a base. Further, the compound (III-a-1), (III-b-1) or a salt thereof formed in the first step reaction is not isolated, but is continuously added by adding a base to the reaction mixture. It is also possible to carry out a two-step reaction.
  • Suitable solvents for the first-stage reaction include, for example, aromatic hydrocarbons such as benzene, toluene, and xylene, dichloromethane, chloroform, 1 Halogenated hydrocarbons such as 2-dichloroethane, ethers such as THF and dioxane, nitriles such as acetonitrile, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate, DMF, DM An aprotic polar solvent such as SO or a mixed solvent thereof is used.
  • the solvent suitable for the second step reaction the same solvent as that used in the first step reaction is used.
  • the reaction of the first step is preferably performed in the presence of a base.
  • a base examples include organic bases such as triethylamine, tripropylamine, ethyldiisopropylamine, DBU, and pyridine; and sodium carbonate.
  • inorganic bases such as potassium carbonate.
  • the amount of the base to be used is generally 1 molar equivalent or more (preferably 1-2 molar equivalents) relative to compound (IV-a-1) or (IV-b-1).
  • the reaction temperature of the first stage reaction is usually about 120 to 150 ° (:, preferably about 0 to 10 °). 0 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the base used in the second step reaction the same base as that used in the first step reaction is used.
  • the amount of the base to be used is generally a catalytic amount to about 10 molar equivalents relative to compound (III-a-1) or (III-b-1).
  • the second step It is possible to add the base required for the reaction at the beginning of the first stage reaction, and use the same base as the base required at the first stage. Can also.
  • a Lewis acid can be added to accelerate the reaction.
  • Lewis acid for example, titanium tetrachloride, zinc chloride, tin tetrachloride, aluminum chloride, boron trifluoride ⁇ ⁇ ethyl ether complex and the like are used.
  • the amount of the Lewis acid to be used is about a catalytic amount to about 1 molar equivalent with respect to the compound (a-a-l) or (III-b-1).
  • the reaction temperature of the second stage reaction is usually about 120-150 ° C, preferably about 0-100 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • R 2Q represents a hydrogen atom or a 6- alkyl group, and other symbols have the same meanings as described above.
  • the alkyl group represented by R 2 G for example, methyl, ethyl, isopropyl and the like are used.
  • Compound (V) is a known compound, or can be easily produced from a known compound. For example, Journal of Medicinal Chemistry, Vol. 18, p. 172 (1975), Tetrahedron's Letters [Tetrahedron Letters] Vol. 12, 3001 (1971), Chemical Abstracts [Chemical Abstracts] Vol.
  • L 3 represents a leaving group, and other symbols are as defined above.
  • Examples of the leaving group represented by L 3 include a halogen atom (eg, fluorine, chlorine, Bromine, iodine, etc.), formula
  • the compound (VI-I) or a salt thereof is usually used in an amount of 1 molar equivalent or more (preferably 1 to 10 molar equivalents) of the compound (VI-a-1), (VI-b-1) or (VI -b- ⁇ ) or react with their salts.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction.
  • Suitable solvents include, for example, nitriles such as acetonitrile, ketones such as acetone and methyl ethyl ketone, esters such as ethyl acetate, and DM.
  • An aprotic polar solvent such as F, DMA, DMSO, or a mixed solvent thereof is used.
  • the reaction using the compound (VI-a-1), (VI-b-1) or a salt thereof is generally preferably performed in the presence of a base.
  • a base is shown in Reaction Scheme 1.
  • the same organic bases, inorganic bases, metal alkoxides, and the like as used in the reaction are used.
  • the base is generally used in the amount of 1 to 5 molar equivalents relative to compound (VII).
  • an iodide such as sodium iodide or potassium iodide or a phase transfer catalyst such as 18-crown-16, 15-crown-5 may be added.
  • the iodide or phase transfer catalyst used here is usually used in an amount of about 1 to 1 molar equivalent relative to compound (VII).
  • a pyridine compound such as pyridine or 4-dimethylaminopyridine can be added to accelerate the reaction.
  • the amount of the pyridine compound used here is usually from a catalytic amount to about 1 molar equivalent to compound (VII).
  • the compound (VI-b- ⁇ ) is a liquid, it is preferable to carry out this reaction without using a solvent.
  • the reaction temperature of this reaction is usually about 0 to 150 ° C, preferably about 10 to 100 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (VI I) or a salt thereof, which is the starting compound of Reaction Scheme 3 is a known compound. Or it can be easily prepared from known compounds.
  • Compound (VI-a-1) (VI-b-1) (VI-b- ⁇ ) or a salt thereof, which is a starting compound of Reaction Scheme 3, is, for example, a halooctane (or aldehyde) compound (eg, Or 3-, haloketone (or aldehyde) compounds (eg, ⁇ -chloropropiophenone) or ⁇ , 3-unsaturated ketone (or aldehyde) compounds (eg, methyl vinyl ketone).
  • a halooctane or aldehyde
  • haloketone or aldehyde
  • ⁇ -chloropropiophenone or ⁇
  • 3-unsaturated ketone or aldehyde
  • the compound (I) or a salt thereof of the present invention the compound (I-a-3), (I-b-3) or a salt thereof can be produced according to the following reaction scheme 4.
  • the salt of the compound (VIII) shown below the same as the above-mentioned salt of the compound (I) can be used.
  • L 4 represents a leaving group, and other symbols have the same meanings as described above.
  • the leaving group represented by L 4 includes, for example, a halogen atom (eg, fluorine, chlorine, bromine, iodine, etc.) or a formula
  • the compound (Il-a-3), (II-b-3) or a salt thereof is usually reacted with 1 mol equivalent or more (preferably 1 to 2 mol equivalent) of the compound (VIII) or a salt thereof. Let it.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • Suitable solvents include, for example, nitriles such as acetonitrile, ketones such as acetone and methylethylketone, and non-protons such as DMF, DMA and DMSO.
  • a polar solvent, alcohols such as methanol and ethanol, water, or a mixed solvent thereof is used.
  • This reaction is generally preferably carried out in the presence of a base.
  • a base the same organic bases, inorganic bases, metal alkoxides and the like as used in the reaction shown in Reaction Scheme 1 are used. These bases are generally used in 1 to 5 molar equivalents relative to compound (II-a-3) or ( ⁇ -b-3).
  • the reaction temperature of this reaction is usually about 0 to 150 ° C, preferably about 10 to 100. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (VIII) or a salt thereof, which is a starting compound in Reaction Scheme 4 is a conventional halogen compound (eg, chloromethyl methyl ether, etc.), a sulfonic acid ester compound (eg, methyl p-toluenesulfonate, etc.), a sulfate compound ( For example, dimethyl sulfate, etc.), and the compound is a known compound, or can be easily produced from a known compound.
  • halogen compound eg, chloromethyl methyl ether, etc.
  • a sulfonic acid ester compound eg, methyl p-toluenesulfonate, etc.
  • a sulfate compound for example, dimethyl sulfate, etc.
  • R 21 represents an alkyl group, and the other symbols have the same meanings as described above.
  • R 21 Represented by R 21.
  • the Bok 6 alkyl group such as methyl, Echiru, isopropyl and the like.
  • the compound (III-a-3) (III-b-3) or a salt thereof is reacted with a base to perform an intramolecular Claisen condensation reaction.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • Suitable solvents include, for example, alcohols such as methanol, ethanol, and isopropyl alcohol; THF, getyl ether, and 1,2-dimethoxyethane.
  • Ethers, aprotic polar solvents such as DMF DMSO, aromatic hydrocarbons such as benzene, toluene, and xylene, or a mixed solvent thereof are used.
  • the base used in this reaction for example, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium tert-butoxide, and inorganic bases such as sodium hydride are used.
  • the amount of the base to be used is a catalytic amount to about 5 mol per 1 mol of compound (Ill-a-3) or (III-b-3).
  • the reaction temperature of this reaction is usually about ⁇ 20150, preferably about 0100. This reaction is completed in about 30 minutes to 30 hours. It can be confirmed by high performance liquid chromatography or the like.
  • the compound (IV-a-3), (IV-b-3) or a salt thereof is usually reacted with 1 mol equivalent or more (preferably 1 to 2 mol equivalent) of the compound (V) or a salt thereof. Let me do it.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction.
  • the appropriate solvent the same solvent as used in the first step of the reaction shown in Reaction Scheme 2 is used.
  • this reaction is preferably performed in the presence of a base.
  • a base the same base as in the reaction in the first step of the reaction shown in Reaction Scheme 2 is used.
  • the amount of the base to be used is generally 1 molar equivalent or more (preferably 1-2 molar equivalents) relative to compound (IV-a-3) or (IV-b-3).
  • reaction temperature of this reaction the time required for completion of the reaction, the method of confirming the completion of the reaction, and the like are the same as those in the reaction of the first step in the reaction shown in Reaction Scheme 2.
  • the compound (VI-I) or a salt thereof is usually used in an amount of 1 molar equivalent or more (preferably 1 to 10 molar equivalents) of the compound (VI-a-3), (VI-b-3), or (VI -b-3 ') or react with their salts.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction.
  • the appropriate solvent the same solvent as used in the reaction shown in Reaction Scheme 3 is used.
  • the reaction using compound (VI-a-3), (VI-b-3) or a salt thereof is generally preferably carried out in the presence of a base. Such a base is shown in Reaction Scheme 3. The same bases as used in the reaction are used.
  • the amount of the base to be used is generally 1 to 5 molar equivalents relative to compound (VII).
  • an iodide such as sodium iodide or potassium iodide may be added.
  • the iodide used here is usually used in a catalytic amount to about 1 molar equivalent relative to the compound (VII).
  • a pyridine compound such as pyridine or 4-dimethylaminopyridine can be added to accelerate the reaction.
  • the amount of the pyridine compound used here depends on the compound (VI I). On the other hand, the amount is usually from a catalyst amount to about 1 molar equivalent.
  • the compound (VI-b-3 ') is a liquid, it is preferable to carry out this reaction without using a solvent. In order to further accelerate this reaction, it is possible to carry out the reaction under pressure in a sealed tube.
  • the reaction temperature of this reaction is usually about 0 to 200 ° C, preferably about 210 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography and the like.
  • Compounds (VI-a-3), (VI-b-3) (VI-b-3 ') or salts thereof, which are the starting compounds of Reaction Scheme 7, are, for example, ⁇ -halocarboxylic acid ester compounds (eg, bromo vinegar). And 3-, halocarboxylic acid ester compounds (eg, 3-ethyl propionate ethyl ester, etc.) or ⁇ , / 3-unsaturated carboxylic acid ester compounds (eg, methyl acrylate, etc.). These are known compounds or can be easily produced from known compounds.
  • Y 7 represents a halogen atom, and other symbols have the same meanings as described above.
  • halogen atom represented by Y 7 examples include fluorine, chlorine, bromine, and iodine. And bromine and chlorine are particularly preferred.
  • the compound (III-c-1), (III-d-1) or a salt thereof is reacted with a radical hydrogenating agent such as triptyltin hydride in the presence of a radical initiator to effect a ring closure reaction.
  • a radical hydrogenating agent such as triptyltin hydride
  • Suitable solvents include, for example, aromatic hydrocarbons such as benzene and toluene.
  • radical initiator used in this reaction examples include 2,2′-azobisisobutyronitrile (hereinafter abbreviated as AIBN), benzoyl peroxide, and triethylporan.
  • AIBN 2,2′-azobisisobutyronitrile
  • the amount of the radical initiator used is usually a catalytic amount based on 1 mol of the compound (III-c-1) or ( ⁇ ⁇ ⁇ -d-1).
  • the amount of the radical hydrogenating agent to be used is generally 1 to 5 molar equivalents relative to compound (III-c-1) or (III-d-1).
  • the reaction temperature of this reaction is usually about 0 to 150 ° C, preferably about 50 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound (IV-c-1), (IV-d-1) or a salt thereof is usually reacted with 1 mol equivalent or more (preferably 1 to 2 mol equivalent) of the compound (IX) or a salt thereof. Let me do it.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction, and as the appropriate solvent, the same solvent as that used in the first step of the reaction shown in Reaction Scheme 2 is used.
  • this reaction is preferably performed in the presence of a base.
  • a base the same base as in the reaction in the first step of the reaction shown in Reaction Scheme 2 is used.
  • the amount of the base to be used is generally 1 mol equivalent or more (preferably 1-2 mol equivalent) relative to compound (IV-C-1) or (IV-d-1).
  • reaction temperature of this reaction the time required for completion of the reaction, the method of confirming the completion of the reaction, and the like are the same as those in the reaction of the first step in the reaction shown in Reaction Scheme 2.
  • the compound (V) can be easily produced by a known method or a method analogous thereto.
  • the compound ( ⁇ ′) can be prepared, for example, by subjecting the compound ( ⁇ ′) to a known method or a method analogous thereto. It can be manufactured more easily.
  • L 5 represents a leaving group, and other symbols have the same meanings as described above.
  • the leaving group represented by L 5 the same as the leaving group L 3 is used as shown in Scheme 3.
  • a halogen atom such as chlorine, bromine or iodine is preferred.
  • compound (VI I) or a salt thereof is usually reacted with at least 1 molar equivalent (preferably 1 to 3 molar equivalents) of compound (X-C-1), (Xd-1) or a salt thereof. Let me do it.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction, and the same solvent as used in the reaction shown in Reaction Scheme 3 is used as a suitable solvent.
  • this reaction is preferably performed in the presence of a base.
  • a base the same base as used in the reaction shown in Reaction Scheme 3 is used.
  • the amount of the base to be used is generally 1 to 5 molar equivalents relative to compound (VII).
  • an iodide such as sodium iodide or potassium iodide may be added.
  • the iodide used here is usually used in a catalytic amount to about 1 molar equivalent relative to compound (VII).
  • the reaction temperature of this reaction is the same as those in the reaction shown in Reaction Scheme 3.
  • the compound (XC-1), (Xd-1) or a salt thereof, which is the starting compound of Reaction Scheme 10, is a usual haloalkyne compound (eg, propargyl bromide, etc.), and is a known compound, Alternatively, it can be easily produced from a known compound.
  • the group R 9 in the compound (Ia) or (Ib) is a group R 9q , Applicable when indicated.
  • Such compounds (I-a-2) and (I-b-2) are obtained by reacting the compounds (I-a-1) and (I-b-1) obtained in the reaction scheme 1 with an oxidizing agent, respectively. It can be obtained by:
  • As the oxidizing agent for example, selenium dioxide, chromium oxide, chromium oxide-pyridine complex and the like are used. These oxidizing agents are generally used at 1 to 10 molar equivalents relative to compound (I-a-1) or (Ib-1).
  • Halogen e.g. fluorine, chlorine, bromine, iodine, etc.
  • R 13 alkyl group which may be substituted one to three, for example, methyl, Echiru, I an isopropyl, triflumizole Ruo Russia methyl and the like
  • halogen e.g. fluorine, chlorine, bromine, iodine
  • 1-3 optionally substituted C 6 in - the 14 Ariru group e.g., phenyl, naphthyl, 4-black port phenyl and the like
  • a halogen e.g.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction.
  • Suitable solvents include, for example, alcohols such as ethanol and tert-butyl alcohol, ethers such as dioxane, carboxylic acids such as acetic acid, and acetic anhydride. Acid anhydrides, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, water, or a mixed solvent thereof.
  • oxidizing agent used in this reaction for example, selenium dioxide, chromium oxide, chromium oxide-pyridine complex and the like are used. These oxidizing agents are generally used at 1 to 10 molar equivalents relative to compound (I-a-1 ′) or (I-b- ⁇ ).
  • the reaction temperature of this reaction is usually about 20 to 150 ° C, preferably about 0 to 100X. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound (Ia-la), (Ib-la) or a salt thereof, which represents the group represented by, is to be produced according to the following reaction scheme 12.
  • alkyl group represented by R 14x those similar to the C 6 alkyl group represented by R 14 are used, and for example, methyl, ethyl and the like are used.
  • the compound (I-a-2a), (Ib-2a) or a salt thereof is usually reacted with 1 mol equivalent or more (preferably 1 to 3 mol equivalent) of the compound (XI) or a salt thereof.
  • the compound (I-a-la), (Ib-la) or a salt thereof is usually reacted with 1 mol equivalent or more (preferably 1 to 3 mol equivalent) of the compound (XI) or a salt thereof.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • Suitable solvents include, for example, alcohols such as methanol and ethanol, and non-polar polar solvents such as DMF and DMA.
  • the reaction temperature of this reaction is usually about 120 to 150 ° C, preferably about 0 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound (XI) or a salt thereof, which is the starting compound in Reaction Scheme 12, is a common hydroxyamine, a 0-alkylhydroxylamine compound (eg, dimethylhydroxylamine, etc.), etc., and is a known compound or a known compound. It can be easily produced from a compound.
  • Ci-e alkyl monocarbonyl groups which may be substituted by 1 to 3 halogens represented by R 14y (for example, fluorine, chlorine, bromine, iodine, etc.) are substituted by 1 to 3 halogens represented by R 14
  • halogens represented by R 14y for example, fluorine, chlorine, bromine, iodine, etc.
  • R 14y The same as the Ci—e alkyl monocarbonyl group which may be used, for example, acetyl, propionyl, trifluoroacetyl and the like are used.
  • the compound (I-b-la ') or a salt thereof as a starting compound is reacted with a compound ( ⁇ ) or a salt thereof having usually 1 mol equivalent or more (preferably 1 to 3 mol equivalent), and each compound is reacted.
  • (1-a-lb) or a salt thereof, or a compound (Ib-lb) or a salt thereof is produced.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • Suitable solvents include, for example, ethers such as THF and dioxane, and halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane. Is used.
  • a base can be added to accelerate the reaction. Examples of such a base include pyridine and triethylamine. The amount of the base to be used is generally 1 to 5 molar equivalents relative to compound (I-a-la ') or (I-b-la').
  • the reaction temperature of this reaction is generally about -20 to 150 ° C, preferably about 0 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (XII) or a salt thereof, which is the starting compound of Reaction Scheme 13 is a common carboxylic acid halide (eg, acetyl chloride, etc.), a carboxylic anhydride (eg, acetic anhydride, etc.), etc., and is a known compound. Or it can be easily prepared from known compounds.
  • groups R 13 and R 14x of the compound (a-la) both have a hydrogen atom.
  • Dehydration reaction of the compound (I-a-la '') or a salt thereof, or the compound (Ib-la '') or a salt thereof of the compound (Ib-la) in which the groups R 13 and R 14 both represent a hydrogen atom To produce a compound (Ia-4) or a salt thereof, or a compound (Ib-4) or a salt thereof, respectively.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction, and suitable solvents include, for example, THF, DMF and the like.
  • suitable solvents include, for example, THF, DMF and the like.
  • a dehydrating reagent used in this reaction for example, a Vilsmeier [Vi1smeyer] reagent prepared from phosphorus oxychloride and DMF is used.
  • a base can be added to accelerate the reaction.
  • bases include, for example, pyridine, triethylamine and the like.
  • the amount of the dehydrating reagent and the base to be used is generally 1 to 5 molar equivalents relative to compound (I-a-la '') or (I-b-la '').
  • the reaction temperature of this reaction is generally about -20 to 150 ° C, preferably about 0 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (Ia-4), (Ib-4) or a salt thereof is a compound (Ia-2a ′) shown below, wherein the group R 13 represents a hydrogen atom among the compounds (Ia-2a). ) Or a salt thereof, or a compound (Ib-2a ′) or a salt thereof shown below, in which the group R 13 represents a hydrogen atom among the compounds (Ib-2a), and reacting them
  • the compound (Ia-la '') or a salt thereof, or the compound (I-b-la '') or a compound thereof is reacted with hydroxylamine or a salt thereof under the conditions of the reaction shown in Scheme 12 to form a compound (Ia-la '') or a salt thereof.
  • After generating the salt react it under the conditions of the reaction shown in Reaction Scheme 14 by adding the dehydrating reagent used in the reaction shown in Reaction Scheme 14 to the reaction mixture without isolation. Can also be produced.
  • a compound (I-a-lc), (Ibl c) or a salt thereof, which represents a group represented by R 13 CH (OH)-(wherein R 13 has the same meaning as described above), is It can also be produced according to the following reaction scheme 15.
  • the compound (I-a-Ic), (I-b-lc) or a salt thereof is produced by reacting the compound (I-a-2a), (I-b-2a) or a salt thereof with a reducing agent.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • suitable solvents include, for example, alcohols such as methanol, ethanol, and isopropyl alcohol, ethers such as THF and dioxane, water, and mixtures thereof.
  • a solvent is used.
  • the reducing agent used in this reaction include sodium borohydride.
  • the amount of the reducing agent to be used is generally about 1 to 5 mol, per 1 mol of compound (I-a-2a) or (I-b-2a).
  • sodium borohydride is used as the reducing agent, it is preferable to add cerium chloride (or a hydrate thereof).
  • cerium chloride or a hydrate thereof
  • the amount of cerium chloride used is usually about 1 to 3 mol per mol of sodium borohydride.
  • the reaction temperature of this reaction is usually about 20 to 150 ° C, preferably about 0 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be
  • each of R 22 may be substituted with 1 to 3 halogen atoms.
  • (I) represents a Cj.g alkyl group or (ii) an alkyl-carbonyl group, and other symbols are as defined above.
  • the compound (Ia-ld), (I-b-ld) or a salt thereof corresponding to the group represented by) can also be produced according to the following reaction scheme 16.
  • Halogen e.g. fluorine, chlorine, bromine, iodine, etc.
  • R 22 as the alkyl group which may be substituted one to three, for example, methyl, Echiru like are used.
  • a C ⁇ 6 alkyl-carbonyl group optionally substituted by 1 to 3 halogens represented by R 22 (eg, fluorine, chlorine, bromine, iodine, etc.)
  • acetyl, propionyl, trifluoroacetyl and the like are used.
  • the leaving group represented by L 6 the same as the leaving group L 3 is used represented by the leaving group L 2 or the reaction diagram formula 3 shown in Reaction Scheme 2.
  • a halogen atom for example, chlorine, bromine, iodine, etc.
  • 6- alkyl-carbonyloxy group for example, acetoxyl group, etc.
  • compound (I-a-Id), (Iblc) or a salt thereof is usually reacted with compound (XIII) or a salt thereof in an amount of 1 mol equivalent or more, and compound (I-a-Id), (1-b-Id) or a salt thereof is produced.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction.
  • the same solvent as that used in the first step of the reaction shown in Reaction Scheme 2 is used.
  • this reaction is preferably performed in the presence of a base.
  • a base include organic bases such as triethylamine, DBU, and pyridine; inorganic bases such as sodium carbonate, potassium carbonate, and sodium hydride; and potassium.
  • Metal alkoxides such as tert-butoxide are used.
  • the amount of these bases to be used is generally 1 molar equivalent or more (preferably 1 to 3 molar equivalents) relative to compounds (I-a-lc) and (I-b-lc).
  • the reaction can be accelerated by adding a silver salt (for example, silver oxide or the like).
  • a silver salt for example, silver oxide or the like.
  • the amount of the silver salt to be used is generally 1 molar equivalent or more (preferably 1-2 molar equivalents) relative to compound (I-a-lc) or (I-b-lc).
  • the reaction can be accelerated by adding a reagent that promotes acylation such as 4-dimethylaminopyridine. it can.
  • the amount of the reactant to be used is generally a catalyst amount to about 1 molar equivalent relative to compound (I-a-lc) or (I-b-lc).
  • the reaction temperature of this reaction is usually about 0 to 150 ° C, preferably about 10 to 100 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (XI II) or a salt thereof, which is the starting compound of Reaction Scheme 16 is, for example, a halogenated hydrocarbon compound (eg, methyl iodide, etc.), a carboxylic acid halide (eg, Acetyl chloride, etc.), carboxylic anhydrides (eg, acetic anhydride, etc.) and the like. These are known compounds or can be easily produced from known compounds.
  • the group R 9p has the formula
  • R 23 R 24 C CR 13 _
  • R 23 and R 24 are each a hydrogen atom, a halogen atom, a group represented by ( ⁇ _ 6 alkyl group, also shows the Haci alkoxy group and the other symbols are as defined above.
  • the compounds (Ia-le), (Ib-le) or salts thereof corresponding to the case shown can also be produced according to the following reaction scheme 17.
  • the salts of the compound (XIV) shown below are described above. The same salts as those of the compound (I) are used.
  • Ph represents a phenyl group, and other symbols have the same meanings as described above.
  • the halogen atom represented by R 23 or R 24 for example, fluorine, chlorine, Bromine and iodine.
  • the 6 alkyl group represented by R 23 or R 24 for example, methyl, Echiru like are used. Also shown are by R 23 or R 24 - The 6 alkoxy groups such as methoxy, ethoxy and the like are used.
  • the compound (Ia-2a), (Ib-2a) or a salt thereof is usually converted to a compound of 1 mol equivalent or more (preferably 1 to 2 mol equivalent) of the ylide compound (XIV) or a salt thereof.
  • a compound (Ial e), (Ible) or a salt thereof is usually converted to a compound of 1 mol equivalent or more (preferably 1 to 2 mol equivalent) of the ylide compound (XIV) or a salt thereof.
  • Suitable solvents include, for example, aliphatic hydrocarbons such as hexane and cyclohexane, aromatic hydrocarbons such as benzene, and getyl ether. And ethers such as THF, nonprotonic polar solvents such as DMS ⁇ , or a mixed solvent thereof.
  • the reaction temperature of this reaction is usually about -80 to 100 ° C, preferably about 170 to 50. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (XIV) or a salt thereof, which is the starting compound of Reaction Scheme 17, is a known compound, or can be easily produced from a known compound.
  • the general formula (XIV) is a known compound, or can be easily produced from a known compound.
  • the phosphonium salt compound represented by the formula [1] is usually used in an amount of at least 1 molar equivalent of a base (for example, inorganic bases such as sodium hydride, metal alkoxides such as potassium tert-butoxide, and organic metals such as butyl lithium and phenyl lithium) Compounds, etc.).
  • a base for example, inorganic bases such as sodium hydride, metal alkoxides such as potassium tert-butoxide, and organic metals such as butyl lithium and phenyl lithium
  • a base for example, inorganic bases such as sodium hydride, metal alkoxides such as potassium tert-butoxide, and organic metals such as butyl lithium and phenyl lithium
  • a base for example, inorganic bases such as sodium hydride, metal alkoxides such as potassium tert-butoxide, and organic metals such as butyl lithium and phenyl lithium
  • the compounds of the present invention (I), (I I- a- 1), (I Ib-1) or of a salt thereof, wherein S ( ⁇ ) groups R 1 in the P R 2 5 (wherein, R 2 5 Table in the six-alkynyl or phenyl group, p is 1 or 2) - is halogen 1-3 amino optionally substituted have good C DOO 6 alkyl group, C 2 - 6 alkenyl group, C 2.
  • X la (X la is the same or different and is substituted with 1 to 3 halogen atoms or halogens) Represents an optionally substituted alkyl group.
  • Ci 6 alkyl group optionally substituted with 1 to 3 halogens represented by R 25 include methyl, ethyl, isopropyl, trifluoromethyl, 2, 2-trifluorethyl and the like.
  • the C 2 _ 6 alkenyl group represented by R 25 for example, Ru Ariru and the like.
  • the C 2 _ 6 alkynyl group represented by R 25 for example, propargyl and the like.
  • the halogen atom represented by X la e.g., fluorine, chlorine, bromine, ® ⁇ iodine or the like is used.
  • alkyl group which may be substituted with 1 to 3 halogen atoms represented by X (eg, fluorine, chlorine, bromine, iodine, etc.) include methyl, ethyl, trifluoromethyl and the like.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction.
  • Suitable solvents include, for example, water, methanol, ethanol, tripropanol, isopropyl alcohol, 1-butanol, tert-butyl alcohol, and other alcohols.
  • Aromatic hydrocarbons such as benzene, toluene, xylene and nitrobenzene, halogenated hydrocarbons such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, ketones such as acetone, and acetonitrile Nitriles, carboxylic acids such as acetic acid and trifluoroacetic acid, aprotic polar solvents such as DMF, and a mixed solvent thereof are used.
  • the oxidizing agent for example, hydrogen peroxide, potassium permanganate, peracetic acid, methacrylo- perbenzoic acid, sodium percarbonate and the like are used.
  • the amount of the oxidizing agent used in this reaction may be an appropriate amount necessary for completing the reaction, but theoretically, the compounds (I-e '), (II-a-le'), ( ⁇ -b -le ') or salts thereof in which p is 1 for the production of 1 mol of the starting compound (Ie), (II-a-le), ( ⁇ -b-le) or their salts
  • the amount that generates one equivalent of active oxygen is determined by the amount of compound (I-e '), (II-a-le'), (II-b-le '), or a salt thereof, for which p is 2. In the production, the amount of the active compound (I-e), (II-a-le), (II-b-le) or an amount capable of generating 2 equivalents of active oxygen per 1 mol of
  • the reaction temperature of this reaction is generally about 160 to 100, preferably about 120 to 60. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin-layer chromatography, high-performance liquid chromatography, or the like.
  • the group R 9p has the formula R 26 S (0) P CH 2 —
  • R 26 represents a ( ⁇ -6 alkyl group, and p has the same meaning as described above.
  • a compound represented by the formula (I-a-lg), (Ib-lg ) Or a salt thereof can also be produced according to the following reaction scheme 19. Further, in the compounds (I-c), (Id) or salts thereof of the present invention, the group R 11 is a compound of the formula R 26 S (O) p-
  • Examples of the alkyl group represented by R 26 include methyl, ethyl, isopropyl and the like.
  • the group R 9 p of the compound (I-a-1) (Ib-1) or a salt thereof is represented by the formula A compound (I-a-lf) or (Ib-lf) or a salt thereof, or a compound thereof (R 26 SCH 2- (wherein R 26 has the same meaning as described above)) I- c), (Id) or a salt thereof, wherein the group R 11 is of the formula
  • This reaction can be performed in a solvent that does not adversely influence the reaction, and the same solvent as the reaction shown in Reaction Scheme 18 is used as a suitable solvent.
  • the same oxidizing agent as used in the reaction shown in Reaction Scheme 18 is used.
  • the amount of the oxidizing agent used in this reaction may be an appropriate amount necessary for completing the reaction, but theoretically, the compounds (Ia-lg), (1-b-lg), (Ic-3), For the production of (Id-3) or a salt thereof in which p is 1, the starting compounds (Ia-If), (Ib-lf), (Ic-2), (Id-2) or their
  • the amount that generates one equivalent of active oxygen per mole of the salt is determined by the amount of compound (I-a-lg), (Ib-lg), (Ic-3), (Id-3) or a salt thereof.
  • the reaction temperature of this reaction is usually about 160 to 100 t :, preferably about 120 to 60 t. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin-layer chromatography, high-performance liquid chromatography, or the like.
  • the group R 9p has the formula R 13 CF 2-
  • the compound (I-a-2a) (Ib-2a) or a salt thereof is usually reacted with at least 1 mol equivalent (preferably 15 mol equivalents) of a fluorinating agent to give the compound (I-a-a).
  • a fluorinating agent preferably 15 mol equivalents
  • This reaction can be carried out in a solvent that does not adversely affect the reaction. Suitable solvents include, for example, aromatic hydrocarbons such as toluene, halogenated hydrocarbons such as dichloromethane and trichlorofluoromethane, and dimethoxyethane. Or a mixed solvent thereof.
  • the fluorinating agent used in this reaction include getylaminosulfate fluoride.
  • the reaction temperature of this reaction is generally about ⁇ 210 ° C., preferably about 0 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound (Ia-2a ') (Ib-2a') or a salt thereof is usually reacted with an organic rhodium complex of 1 mole equivalent or more (preferably 12 mole equivalents) to carry out a decarbonylation reaction. Then, compound (I-a-li) (Ib-li) or a salt thereof is produced.
  • This reaction can be carried out in a solvent that does not adversely influence the reaction. Suitable solvents include, for example, aromatic hydrocarbons such as benzene and xylene, and nitriles such as acetonitrile and benzonitrile.
  • organorhodium complex used in this reaction examples include chlorotris (triphenylphosphine) rhodium and the like.
  • the reaction temperature of this reaction is usually about 0 200 ° C, preferably about 50 150 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • the compound (II′-a-1) or a salt thereof in which the group R lx in the compound ( ⁇ -a) represents a hydrogen atom, or the group R lx in the compound ( ⁇ -b) represents a hydrogen atom The compound (Il'-b-1) or its salt is reacted with a halogenating agent to convert the hydroxy group on the carbon atom to which the group R 9p is bonded into a highly removable substituent such as a halogen atom.
  • the carboxylic acid moiety is converted into an acid halide, which is usually reacted with 1 mole equivalent or more (preferably 1 to 3 mole equivalent) of the compound (XV) to carry out the amide formation reaction.
  • the hydrogen atom on the carbon atom to which the group R 8 is bonded and the hydroxy group are derived from the starting compound ( ⁇ -a-1) in the same manner as in the reaction shown in Reaction Scheme 1.
  • the compound (I-a-lr) which is considered to be formed by elimination is usually obtained, but when the group R 9 p has a hydrogen atom involved in the elimination reaction, that is, when the group R 11 R 12 CH In some cases, the compound (I-c-r) formed by elimination of the hydrogen atom and the hydroxy group may be obtained.
  • the compound ( ⁇ '-b-1) is used as a starting compound, the compound (Ib-lr) is usually obtained for the same reason, but the compound (Idr) may also be obtained.
  • Suitable solvents include, for example, aromatic hydrocarbons such as benzene and toluene, dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane.
  • Halogenated hydrocarbons such as benzene, benzene, 0-dichlorobenzene, ethers such as THF and dioxane, nitriles such as acetate nitrile, ketones such as acetone and methyl ethyl ketone, and acetate Esters such as chill, aprotic polar solvents such as DMF, DMA and DMSO, or a mixed solvent thereof are used.
  • a reactant such as a combination of thionyl chloride, triphenylphosphine and carbon tetrachloride is used.
  • the amount of these reactants to be used is generally at least 2 molar equivalents (preferably 2 to 10 molar equivalents) relative to compound (Il'-a-1) or ( ⁇ '-b-1).
  • carbon tetrachloride can be used as a part of the solvent.
  • this reaction is preferably performed in the presence of a base.
  • a base examples include organic bases such as triethylamine, tripropylamine, ethyldiisopropylamine, pyridine, collidine, lutidine, and DBU; Inorganic bases such as sodium and potassium carbonate are used.
  • the base is used usually in an amount of 2 to 10 molar equivalents relative to the compound ( ⁇ -a-1) or ( ⁇ -b-1).
  • the reaction temperature of this reaction is usually about 20 to 150 ° C, preferably about 0 to 100 ° C. This reaction is completed in about 30 minutes to 30 hours, and the completion can be confirmed by thin layer chromatography, high performance liquid chromatography, or the like.
  • Compound (XV) or a salt thereof, which is the starting compound of Reaction Scheme 22, is a common amine compound and is a known compound or can be easily produced from a known compound.
  • Hydrogenolysis is carried out by reacting a compound ( ⁇ -b-2) or a salt thereof with hydrogen gas, usually at least 1 molar equivalent, in the presence of a transition metal catalyst for catalytic hydrogenation.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction. Suitable solvents include, for example, alcohols such as methanol and ethanol, ethers such as THF and diisopropyl ether, esters such as ethyl acetate, water, Alternatively, a mixed solvent thereof is used.
  • the pressure of hydrogen gas used in this reaction is about 15 atm.
  • transition metal catalyst used in this reaction examples include palladium-activated carbon, and the amount thereof is a catalytic amount based on the compound (Il'-a-2) or (Il'-b-2). You.
  • the reaction temperature of this reaction is usually about 60 ° C (:, preferably, about 1030 ° C.) This reaction is completed in about 30 minutes to 30 hours, and the completion is confirmed by thin layer chromatography, high performance liquid chromatography, etc. it can.
  • the compound (IV′-a-2), (IV-b-2) or a salt thereof is reacted with the compound (V) or a salt thereof in an amount of usually 1 molar equivalent or more, and the compound ( I II'-a-2), (III'-b-2) or a salt thereof, and then, as a second step, the compound ( ⁇ -a-2), (III'-b-2) or a salt thereof.
  • the salt is reacted with a base to effect a ring-forming reaction.
  • the compounds ( ⁇ -a-2), (III'-b-2) or their salts are new compounds.
  • This reaction is a two-step reaction, and is formed in the first step by reacting compound (IV'-a-2), (IV-b-2) or a salt thereof with compound (V) or a salt thereof.
  • compound (IV'-a-2), (IV-b-2) or a salt thereof After isolating compounds ( ⁇ -a-2), (III'-b-2) or their salts, it is possible to carry out a ring-forming reaction by the action of a base. It is also necessary to add a base to the reaction mixture without isolating the compounds (II ⁇ -a-2), (I ⁇ '-b-2) or their salts formed in the first step reaction. , It is also possible to carry out the second stage reaction.
  • This reaction can be carried out in a solvent that does not adversely affect the reaction, and a suitable solvent for the first-stage reaction is the same solvent used in the first-stage reaction among the reactions shown in Reaction Scheme 2. .
  • a suitable solvent for the second step reaction the same solvent as that used in the first step reaction is used.
  • the amount of the base to be used is generally 1 molar equivalent or more relative to compound (IV'-a-2) or (IV'-b-2).
  • the reaction temperature of the first stage reaction is usually about 170-100 ° C, preferably about 150-30 ° C. This reaction is completed in about 30 minutes to several days, and the completion can be confirmed by thin-layer chromatography, high-performance liquid chromatography, or the like.
  • the base used in the second step reaction the same base as that used in the first step reaction is used.
  • the amount of the base to be used is generally a catalytic amount to about 10 molar equivalents relative to compound ( ⁇ -a-2) or (II I'-b-2).
  • the compound ( ⁇ ⁇ -a-2) or (III'-b-2) or a salt thereof formed in the first step reaction is not isolated and the subsequent second step reaction is performed, the second step
  • the base required for the two-step reaction can be added at the beginning of the first step reaction, and the same base as that required for the first step can be used as the base.
  • a Lewis acid can be added to accelerate the reaction.
  • a Lewis acid for example, titanium tetrachloride, zinc chloride, tin tetrachloride, aluminum chloride, boron trifluoride / getyl ether complex and the like are used.
  • the amount of the Lewis acid to be used is about a catalytic amount to about 1 molar equivalent with respect to the compound (a-a-2) or ( ⁇ -b-2).
  • the reaction temperature of the second stage reaction is usually about -70 to 100 ° C (:, preferably, about -50 to 30 ° C.)
  • the reaction is completed in about 30 minutes to several days, and the reaction is completed by thin-layer chromatography. It can be confirmed by luffy, high performance liquid chromatography, etc.
  • compound ( ⁇ -2) or a salt thereof is usually used in an amount of 1 molar equivalent or more (preferably:! To 10 molar equivalents) of compound (VI-a-1) (VI-b-1) (VI-b-1). -1 ') Or react with their salts.
  • This reaction can be performed in a solvent that does not adversely influence the reaction, and the same solvent as the reaction shown in Reaction Scheme 3 is used as a suitable solvent.
  • the reaction using compound (VI-a-1) (VI-b-1) or a salt thereof is generally preferably performed in the presence of a base.
  • a base is represented by Reaction Scheme 1.
  • the same organic bases, inorganic bases, metal alkoxides and the like as used in the reaction are used.
  • the base is usually used at 15 molar equivalents with respect to the compound (VI (-2).
  • an iodide such as sodium iodide or potassium iodide or a phase transfer catalyst such as 18-crown-615-crown-5 may be added.
  • the iodide or phase transfer catalyst used here is usually used in an amount of about 1 to 1 molar equivalent based on the compound ( ⁇ -2).
  • a pyridine compound such as pyridine or 4-dimethylaminopyridine can be added to accelerate the reaction.
  • the amount of the pyridine compound used here is generally from a catalytic amount to about 1 molar equivalent to the compound (VI ⁇ -2).
  • the compound (VI-b-II) is a liquid, it is preferable to carry out this reaction without using a solvent.
  • the reaction temperature of this reaction is usually about 0 150 ° (:, preferably, about 10 100.
  • the reaction is completed in about 30 minutes to several days, and the completion is confirmed by thin layer chromatography, high performance liquid chromatography, etc. it can.
  • Compound ( ⁇ -2), which is the starting compound of Reaction Scheme 25, or a salt thereof is a known compound. Or can be easily produced from known compounds. For example, it can be produced by a method described in Journal of the American Chemical Society [Journal of the American Chemical Society], Vol. 103, p. 6127 (1981) or a method analogous thereto.
  • the compound (I-a-lr), (I-c-r), (I-b-lr), (I-d-r) or a salt thereof of the present invention can also be produced according to the following reaction scheme 26.
  • L 7 represents a halogen atom, and other symbols have the same meanings as described above.

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Abstract

L'invention concerne des composés d'amide cyclique pourvus de deux substituants en position α du groupe carbonyle ainsi que les sels desdits composés. Ceux-ci exercent, à doses réduites, un excellent effet herbicide sur une vaste gamme de plantes nuisibles (par exemple, des plantes nuisibles des plaines et des montagnes) sans occasionner de dommages chimiques sur les plantes cultivées, telles que le riz, le blé, l'orge, le soja, le maïs et le coton. Ces composés produisent ainsi un excellent effet herbicide sélectif et durable. En outre, ces composés ne sont guère toxiques pour les mammifères, poissons et fruits de mer et n'exercent aucun effet polluant sur l'environnement. Ils peuvent donc être utilisés en toute sécurité comme herbicides en plaine, en montagne, dans des vergers ou des terres non cultivées.
PCT/JP1999/004327 1998-08-11 1999-08-10 Composes d'amide cyclique, procedes de production correspondants, intermediaires correspondants et herbicides Ceased WO2000009481A1 (fr)

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EP1254892A3 (fr) * 2001-04-23 2002-12-11 Daicel Chemical Industries, Ltd. Dérivés ou sels d'aminométhyle cyclopropyle cétone N-substitué et un procédé pour leur préparation
US6710210B2 (en) 2001-04-23 2004-03-23 Daicel Chemical Industries, Ltd. N-substituted-aminomethyl cyclopropyl ketone derivatives or salts thereof and production process therefor
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US7838530B2 (en) 2003-09-25 2010-11-23 Astrazeneca Ab Quinazoline derivatives as antiproliferative agents
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US7632840B2 (en) 2004-02-03 2009-12-15 Astrazeneca Ab Quinazoline compounds for the treatment of hyperproliferative disorders
US7820683B2 (en) 2005-09-20 2010-10-26 Astrazeneca Ab 4-(1H-indazol-5-yl-amino)-quinazoline compounds as erbB receptor tyrosine kinase inhibitors for the treatment of cancer
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