[go: up one dir, main page]

WO2013061973A1 - Heteroaryl sulfonamide compound or salt thereof - Google Patents

Heteroaryl sulfonamide compound or salt thereof Download PDF

Info

Publication number
WO2013061973A1
WO2013061973A1 PCT/JP2012/077373 JP2012077373W WO2013061973A1 WO 2013061973 A1 WO2013061973 A1 WO 2013061973A1 JP 2012077373 W JP2012077373 W JP 2012077373W WO 2013061973 A1 WO2013061973 A1 WO 2013061973A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
halo
optionally substituted
alkoxycarbonyl
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2012/077373
Other languages
French (fr)
Japanese (ja)
Inventor
大野　研
寿彦 植木
地 伏木田
達哉 大北
冴香 小森
優太 田澤
祐介 熊倉
賢二 井櫻
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Publication of WO2013061973A1 publication Critical patent/WO2013061973A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing >N—S—C≡(Hal)3 groups
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/08—Bridged systems

Definitions

  • the present invention relates to a novel heteroarylsulfonamide compound or salt thereof useful as an active ingredient of a herbicide, and a herbicide containing them.
  • Patent Document 1 disclose haloalkylsulfonanilide derivatives having a certain structure. However, they do not specifically disclose the heteroarylsulfonamide compounds represented by the general formula (I) described later.
  • the present inventors have made various studies in order to find a more excellent herbicide that can solve the above-mentioned problems. As a result, the present inventors have found that the novel heteroarylsulfonamide-based compound exhibits a high herbicidal effect on various weeds with a low dosage, and also exhibits high safety for various useful crops, thereby completing the present invention.
  • A is an oxygen atom, sulfur atom, SO, SO 2 or CR 8 R 9 ;
  • W is an oxygen atom or sulfur atom;
  • Z is an oxygen atom, sulfur atom or CR 10 R 11 ;
  • m Is 0, 1 or 2;
  • n is 0, 1 or 2; provided that 0 ⁇ n + m ⁇ 3;
  • q is 0, 1 or 2;
  • R 1 is haloC 1 -C 6 R 2 is a hydrogen atom, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo C 3 -C 6 alkylcarbonyl, cyclo C 3 -C 6 Alkyl C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, phenyl C 2 -C 6 alkenylcarbonyl optionally substituted with Y, phenylcarbonyl
  • R 7 , R 8 , R 9 , R 10 or R 11 can be combined to form an optionally substituted 3- to 8-membered ring, which is an oxygen atom, sulfur atom or nitrogen atom (the nitrogen atom may be substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl, by C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl) May contain 1 or 2 heteroatoms et selected; R 4, R 5, R 6, R 7, R 8, R 9, R 10 and R 11, adjacent the carbon atom to which they are attached Can be attached to any R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 on the combined carbon atom; Y is a halogen atom, C 1 -C 6 alkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C may be substituted with alkyl C 3 -C 6 cycl
  • the present invention also provides a herbicide containing the heteroarylsulfonamide compound of general formula (I) or a salt thereof as an active ingredient, an herbicidally effective amount of the compound or a salt thereof, an undesirable plant or a place where it grows.
  • the present invention relates to a method for controlling undesired plants or suppressing their growth.
  • the heteroarylsulfonamide compound of the general formula (I) or a salt thereof realizes a significant improvement in herbicidal activity against undesirable plants (weeds) as compared to similar conventional compounds. In addition, it has high safety for crops.
  • halogen atom or the halogen as a substituent in the general formula (I) examples include fluorine, chlorine, bromine and iodine atoms.
  • the number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
  • alkyl or alkyl moiety in the general formula (I) examples include a straight chain such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, neopentyl, and normal hexyl.
  • Examples include a branched C 1 -C 12 group. Depending on the position of the substituent, it may be C 1 -C 6 .
  • alkoxy or alkoxy moiety in the general formula (I) examples include linear or branched C 1 -C such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, dodecyloxy and the like. There are 12 groups. Depending on the position of the substituent, it may be C 1 -C 6 .
  • alkenyl or alkenyl moiety in the general formula (I) examples include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl and 2-methyl-2.
  • -Propenyl 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3-dimethyl-2 -Linear or branched C 2 -C 6 groups such as butenyl.
  • alkynyl or alkynyl moiety in the general formula (I) examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl- Examples thereof include linear or branched C 2 -C 6 groups such as 3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl.
  • Examples of the cycloalkyl or cycloalkyl moiety in the general formula (I) include C 3 -C 6 groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
  • the cycloalkoxy moiety in the general formula (I) represents a (cycloalkyl) -O— group, for example, a C 3 -C 6 group such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, etc. Can be mentioned.
  • C 1 -C 6 alkylcarbonyl or “C 1 -C 6 alkylcarbonyl moiety” in the general formula (I) is a compound in which the C 1 -C 6 alkyl group is bonded to a carbonyl group (C 1 -C 6 Alkyl) -C ( ⁇ O) — group, derived from a linear or branched aliphatic carboxylic acid having 2 to 7 carbon atoms, such as acetyl, propionyl, isopropionyl, butyryl, pivaloyl, etc.
  • An alkylcarbonyl group is a compound in which the C 1 -C 6 alkyl group is bonded to a carbonyl group (C 1 -C 6 Alkyl) -C ( ⁇ O) — group, derived from a linear or branched aliphatic carboxylic acid having 2 to 7 carbon atoms, such as acetyl, propionyl, isopropionyl, butyryl,
  • C 2 -C 6 alkenylcarbonyl or “C 2 -C 6 alkenylcarbonyl moiety” in the general formula (I) is a compound in which the C 2 -C 6 alkenyl group and the carbonyl group are bonded (C 2 -C 6 Alkenyl) -C ( ⁇ O) — group such as acryloyl, crotonoyl, methacryloyl, 2-methyl-2-butenoyl and the like.
  • CycloC 3 -C 6 alkylcarbonyl or “C 3 -C 6 cycloalkylcarbonyl moiety” in formula (I) is a compound in which the above-mentioned cyclo C 3 -C 6 alkyl group and a carbonyl group are bonded (C 3 -C 6 cycloalkyl) -C ( ⁇ O) — group, for example, groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl and the like.
  • the “di-C 1 -C 6 alkylaminocarbonyl in which two C 1 -C 6 alkyls on the nitrogen atom may be bonded to each other to form a 3- to 8-membered ring” in the general formula (I) is, for example, The following structures are mentioned.
  • R 4 and R 5 , R 6 and R 7 , R 8 and R 9 and R 10 and R 11 are bonded to each other to form an optionally substituted 3- to 7-membered ring.
  • the 3- to 7-membered ring can be an oxygen atom, a sulfur atom or a nitrogen atom (wherein the nitrogen atom is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 may contain 1 or 2 heteroatoms selected from may also be) substituted by cycloalkyl.
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 together with the carbon to which each is bonded, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, epoxy, tetrahydrofuran , Piperidine and the like can be formed.
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are any R on a carbon atom different from the carbon atom to which each is bonded.
  • 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 can be combined to form an optionally substituted 3- to 8-membered ring.
  • the member ring may be an oxygen atom, a sulfur atom or a nitrogen atom, which may be substituted by C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl.
  • heteroatoms selected from the above may be included.
  • cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, epoxy, tetrahydrofuran, piperidine and the like can be formed.
  • the carbon may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, a halogen atom, a hydroxyl group, an oxo group, etc. Examples include the following structures.
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are any R 4 on the carbon atom adjacent to the carbon atom to which they are bonded. , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 , for example, a double bond can be formed.
  • A is an oxygen atom, sulfur atom, SO, SO 2 or CR 8 R 9 ;
  • W is an oxygen atom or sulfur atom;
  • Z is an oxygen atom, sulfur atom or CR 10 R 11 ;
  • m is 0, 1 or 2;
  • n is 0, 1 or 2; provided that 0 ⁇ n + m ⁇ 3;
  • q is 0, 1 or 2;
  • R 1 is halo C 1 -C 6 alkyl;
  • R 2 is hydrogen atom or C 1 -C 12 alkoxycarbonyl;
  • R 3 is halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted optionally C 3 -C be 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl,
  • C 3 -C 6 cycloalkyl halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, phenyl optionally substituted with Y, phenyl optionally substituted with Y C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, hydroxyl or cyano; R 4 and R 5 , R 6 and R 7 , R 8 and R 9 and R 10 and R 11 can be bonded to each other to form an optionally substituted 3- to 7-membered ring.
  • Is an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is a C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cyclo 1 or 2 heteroatoms selected from (which may be substituted by alkyl) or may form an olefin, carbonyl or thiocarbonyl;
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , on a carbon atom different from the carbon atom to which each is bonded.
  • R 10 or R 11 can combine with R 10 or R 11 to form an optionally substituted 3- to 8-membered ring, and the 3- to 8-membered ring is an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is 1 or 2 heteroatoms selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl) Well; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R on the carbon atom adjacent to the carbon atom to which they are attached.
  • Y is a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl optionally substituted with C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 Cycloalkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo C
  • a in the general formula (I) includes —O—, —S—, —SO—, —SO 2 —, —CH 2 —, —CHMe—, —CHEt—, —CMe 2 —, —CHPh. —, —CHCF 3 —, and —C ( ⁇ O) — are more preferable (where Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group).
  • n-Pr is represents an n-propyl group.
  • R 1 in the general formula (I) is more preferably —CHF 2 , —CF 3 , —CCl 3 , —CH 2 CF 3 .
  • R 2 in the general formula (I) includes —H, —Me, —Et, —n—Pr, —i—Pr, —c—Pr, —n—Bu, —COMe, —COEt, —COn—.
  • n-Pr is an i-propyl group
  • c-Pr is a cyclopropyl group
  • n-Bu is an n-butyl group
  • i-Bu is an i-butyl group
  • s-Bu is a sec-butyl group
  • t-Bu is tert-butyl group
  • c-Bu is cyclobutyl group
  • n-C 5 H 11 is n-pentyl group
  • n-C 6 H 13 is n-hexyl group
  • n-C 7 H 15 is n-heptyl group
  • N-C 8 H 17 is an n-octyl group
  • n-C 9 H 19 is an n-nonyl group
  • n-C 10 H 21 is an n-decyl group
  • n-C 11 H 23 is an n-undecyl group
  • n-C 12 H 25 represents an n-dodec
  • R 4 and R 5 in the general formula (I) include —H, —Me, —Et, —Ph, ⁇ O, —CO 2 H, —CO 2 Me, —CO 2 Et, —CO 2 n— Bu and -CN are more preferable.
  • R 6 and R 7 are —H, —OH, —Cl, —Me, —Et, —n—Pr, —i—Pr, —c—Pr, —Ph, — ( CH 2 ) 4 —, — (CH 2 ) 5 —, — (CH 2 ) 6 —, — (CH 2 ) 2 —O— (CH 2 ) 2 —, —OCOCH 3 , —CF 3 , —CH 2 Cl Is more preferable.
  • heteroarylsulfonamide-based compound examples include compounds obtained by appropriately combining the above preferred substituents of A, Z and R 1 to R 7 in the general formula (I).
  • Specific examples include various compounds described in Examples, and particularly preferable specific examples include compounds measuring physical properties among various compounds described in Examples.
  • the salt of the heteroarylsulfonamide compound of the general formula (I) includes any salt that is agriculturally acceptable.
  • an alkali metal salt such as a sodium salt or a potassium salt
  • a magnesium salt such as calcium salts
  • amine salts such as dimethylamine salts and triethylamine salts
  • inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates
  • acetates and methanesulfonates Such organic acid salts.
  • the present invention includes both isomers and isomer mixtures.
  • isomers are described as a mixture.
  • the present invention includes various isomers other than the isomers within the scope of common technical knowledge in the technical field.
  • those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.
  • heteroarylsulfonamide-based compound of the general formula (I) or a salt thereof (hereinafter abbreviated as the compound according to the present invention) can be produced according to the following production methods and ordinary salt production methods. It is not limited to the method.
  • R 2 -a is C 1 -C 12.
  • L represents a leaving group such as a halogen atom.
  • the above reaction can be performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent that is inert to the reaction, such as halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, Aromatic hydrocarbons such as chlorobenzene; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethyl Aprotic polar solvents such as phosphoric acid triamide (HMPA), sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether
  • the above reaction can be performed in the presence of a base as necessary.
  • the base may be either an organic base or an inorganic base.
  • organic base include tertiary amines such as triethylamine and diisopropylethylamine; 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); pyridine; 4- (dimethylamino) pyridine; Examples include 6-lutidine.
  • the inorganic base examples include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium methoxide, sodium ethoxide, Examples include alkali metal alkoxides such as potassium tertiary butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkyls such as butyl lithium; alkali metal carboxylates such as sodium acetate and potassium acetate. As the base, one or more of these may be appropriately selected and mixed for use.
  • phase transfer catalyst examples include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown 6-ether;
  • phase transfer catalyst include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown 6-ether;
  • the above reaction can be performed in the presence of an additive such as trimethylamine hydrochloride.
  • the reaction temperature for the above reaction is usually within the range of 0 ° C. to 150 ° C., desirably within the range of the boiling point of the solvent used from 0 ° C., and the reaction time is usually within the range of 1 minute to 48 hours.
  • the compound represented by the general formula (Ia) is obtained by reacting an intermediate (II) that can be synthesized by the method described below with an intermediate (III) that is commercially available or that can be synthesized according to a known method. Can be synthesized.
  • the above reaction can be performed in the presence of a solvent, if necessary.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, Aromatic hydrocarbons such as chlorobenzene; hydrocarbons such as normal hexane and normal heptane; esters such as methyl acetate, ethyl acetate and propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide Aprotic polar solvents such as (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary butyl methyl ether, 1,4
  • phase transfer catalyst examples include the same catalysts as those exemplified in the production method [1].
  • the above reaction can be performed in the presence of a base as necessary.
  • the base may be either an organic base or an inorganic base, and examples thereof include the same bases as exemplified in the production method [1].
  • As the base one or more of these may be appropriately selected and mixed for use.
  • the above reaction can be carried out in the presence of an acid catalyst as necessary.
  • the acid catalyst include organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid and trifluoromethanesulfonic acid; inorganic acids such as hydrochloric acid, sulfuric acid and hydrogen bromide; zinc chloride Lewis acids such as titanium tetrachloride, tin chloride, aluminum chloride, iron chloride, boron trifluoride-ether complex, and the like.
  • the reaction temperature of the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the reflux temperature, and the reaction time is usually in the range of 1 minute to 72 hours.
  • R 2-b is C 1 -C 12. Alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo (C 3 -C 6 ) alkylcarbonyl, cyclo (C 3 -C 6 ) alkyl (C 1 -C 6 ) alkylcarbonyl, (C 2 -C 6 ) alkenylcarbonyl, phenyl (C 2 -C 6 ) alkenylcarbonyl optionally substituted with Y, phenylcarbonyl optionally substituted with Y, heterocyclic carbonyl optionally substituted with Y, halo (C 1 -C 12 ) alkoxycarbonyl, cyclo (C 3 -C 6 ) alkoxycarbonyl optionally
  • a base can be used.
  • the base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; calcium carbonate and barium carbonate.
  • Alkaline earth metal carbonates such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide. It is done. As the base, one or more of these may be appropriately selected and mixed for use.
  • the above reaction can be carried out in the presence of a solvent.
  • a solvent Any solvent can be used as long as it is inert to the reaction.
  • alcohols such as methanol, ethanol and isopropanol; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) ), Aprotic polar solvents such as dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2 -Ethers such as dimethoxyethane; water and the like.
  • the solvent one or more of these can be appropriately selected.
  • the reaction temperature for the above reaction is usually within a range of 0 ° C. to 100 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.
  • halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, and carbon tetrachloride; benzene, toluene, xylene, Aromatic hydrocarbons such as nitrobenzene and chlorobenzene; hydrocarbons such as normal hexane and normal heptane; diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane And ethers such as As the solvent, one or more of these can be appropriately selected.
  • the reaction temperature for the above reaction is usually within a range of 0 ° C. to 150 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.
  • R 2-c is C 1 -C 12 alkoxycarbonyl; R 3-a represents bromine or iodine.
  • an alkylcarbonyl compound (Ih) is obtained by acid treatment of the vinyl ether compound (Ig) produced by the still coupling reaction using thienyl halide (If) and a palladium catalyst of a tin reagent. It is a reaction.
  • the above reaction can be performed in the presence of a solvent, if necessary.
  • a solvent Any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, nitrobenzene and chlorobenzene; acetonitrile, N, N-dimethylformamide (DMF), Aprotic polar solvents such as dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1, And ethers such as 2-dimethoxyethane.
  • the solvent one or more of these can be appropriately selected.
  • the reaction temperature for the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.
  • the reaction temperature for the above reaction is usually within a range of 0 ° C. to 100 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.
  • the above reaction can be performed in the presence of a base as necessary.
  • the base may be either an organic base or an inorganic base, and examples thereof include the same bases as exemplified in the production method [1].
  • As the base one or more of these may be appropriately selected and mixed for use.
  • the reaction temperature for the above reaction is usually in the range of ⁇ 70 ° C. to 150 ° C., desirably in the range of ⁇ 20 ° C. to 50 ° C., and the reaction time is usually in the range of 1 minute to 72 hours.
  • the above reaction can be performed under an inert gas as necessary.
  • the inert gas include argon gas and nitrogen gas.
  • the above reaction can be performed in the presence of a base as necessary.
  • the base may be either an organic base or an inorganic base.
  • the organic base include ammonia and hydroxylamine.
  • an inorganic base the base similar to the base illustrated to manufacturing method [1] is mentioned.
  • the base one or more of these may be appropriately selected and mixed for use.
  • phase transfer catalyst examples include the same catalysts as those exemplified in the production method [1].
  • the reaction temperature for the above reaction is usually within a range of 0 ° C. to 150 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.
  • the solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the production method [3].
  • the solvent one or more of these can be appropriately selected.
  • the reaction temperature for the above reaction is usually within the range of -70 ° C. to 150 ° C., preferably within the range of 0 ° C. to 100 ° C., and the reaction time is usually within the range of 1 minute to 72 hours.
  • the above reaction can be carried out in the presence of a solvent.
  • the solvent used may be any solvent inert to the reaction, such as halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, Aromatic hydrocarbons such as chlorobenzene; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane, and the like.
  • halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride
  • benzene toluene, xylene
  • Aromatic hydrocarbons such as chlorobenzene
  • ethers such as diethyl
  • the reaction temperature for the above reaction is usually within a range of -70 ° C to 150 ° C, and the reaction time is usually within a range of 1 minute to 72 hours.
  • the above reaction can be performed under an inert gas as necessary.
  • the inert gas include argon gas and nitrogen gas.
  • R 3-a and R 12 are as described above.
  • R 3-b is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl.
  • the above reaction is a reaction for synthesizing the compound (Vb) by Suzuki coupling of thienyl halide (Va) and a boron derivative.
  • any catalyst generally used in the Suzuki coupling reaction may be used.
  • Pd 2 (dba) 3 Pd (PPh 3 ) 4, Pd (dppf) 2 Cl 2, Pd (OAc) 2 and the like, and can be carried out in the presence of a ligand as necessary.
  • the ligand include triphenylphosphine, tricyclohexylphosphine, and tritertiarybutylphosphine.
  • the boron derivatives used in the above reaction may be those generally used for Suzuki coupling, for example, trialkylboranes such as triethylborane, phenylboronic acid, cyclopropylboronic acid and the like.
  • trialkylboranes such as triethylborane, phenylboronic acid, cyclopropylboronic acid and the like.
  • boronic acids and boronic acid esters such as 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.
  • the above reaction can be performed in the presence of a solvent, if necessary.
  • a solvent Any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, nitrobenzene and chlorobenzene
  • esters such as methyl acetate, ethyl acetate and propyl acetate.
  • Aprotic polar solvents such as acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary Examples include ethers such as butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane; alcohols such as methanol, ethanol and isopropanol; water and the like. As the solvent, one or more of these can be appropriately selected.
  • the above reaction can be performed in the presence of a base as necessary.
  • a base for example, alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal carbonates such as sodium bicarbonate and potassium bicarbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; water Examples thereof include alkali metal hydroxides such as lithium oxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide.
  • the base one or more of these may be appropriately selected and mixed for use.
  • the reaction temperature for the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.
  • R 3-c represents fluorine, chlorine, bromine and iodine
  • R 3-d represents hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted C 3 may be -C 6 cycloalkyl, halo C 1 -C 6 alkyl, phenyl which may be substituted by Y Show.
  • the above reaction is a reaction in which the thiophene ring ⁇ -position is lithiated and then the thiophene ring ⁇ -position is halogenated with a halogenating agent.
  • the lithiation reagent used include alkyllithiums such as normal butyllithium and tertiary butyllithium, and lithium amides such as lithium diisopropylamide (LDA).
  • halogenating agent examples include 1,2-dibromo-1,1,2,2-tetrachloroethane, N-fluorobenzenesulfonimide, iodine and the like.
  • the solvent used in the above reaction may be any solvent as long as it is inert to the reaction.
  • hydrocarbons such as normal hexane and normal heptane; diethyl ether, tertiary butyl methyl ether and 1,4-dioxane.
  • Ethers such as tetrahydrofuran (THF) and 1,2-dimethoxyethane; dimethylpropylene urea (DMPU); hexamethylphosphoramide (HMPA) and the like.
  • THF tetrahydrofuran
  • DMPU dimethylpropylene urea
  • HMPA hexamethylphosphoramide
  • the reaction temperature of the above lithiation reaction (step 4-1) is usually in the range of ⁇ 80 ° C. to ⁇ 20 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.
  • the reaction temperature of the halogenation reaction (step 4-2) is usually in the range of ⁇ 80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.
  • the above reaction can be performed under an inert gas as necessary.
  • the inert gas include argon gas and nitrogen gas.
  • the above reaction is a reaction in which the ⁇ -position of the thiophene ring is lithiated by a halogen-lithium exchange reaction and then the ⁇ -position of the thiophene ring is fluorinated by a fluorinating agent.
  • the lithiation reagent to be used include the same lithiation reagents as in the intermediate production method [4].
  • the fluorinating agent used include N-fluorobenzenesulfonimide.
  • the solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the intermediate production method [4].
  • the solvent one or more of these can be appropriately selected.
  • the reaction temperature of the above lithiation reaction (step 4-1) is usually in the range of ⁇ 80 ° C. to ⁇ 20 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.
  • the reaction temperature of the halogenation reaction (step 4-2) is usually in the range of ⁇ 80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.
  • the above reaction can be performed under an inert gas as necessary.
  • the inert gas include argon gas and nitrogen gas.
  • R 3-e is hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 2 -C 6 alkenyl. , C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted optionally C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 (Alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, phenyl or cyano optionally substituted with Y)
  • the above reaction is a reaction for synthesizing compound (IV-i) or (IV-k) by Suzuki coupling of thienyl halide (IV-h) or (IV-j)
  • the solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the intermediate production method [4].
  • the solvent one or more of these can be appropriately selected.
  • the reaction temperature of the above lithiation reaction (Step 7-1) is usually within a range of ⁇ 80 ° C. to ⁇ 20 ° C., and the reaction time is usually within a range of 1 minute to 24 hours.
  • the reaction temperature of the formylation reaction (step 7-2) is usually in the range of ⁇ 80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.
  • the above reaction can be performed under an inert gas as necessary.
  • the inert gas include argon gas and nitrogen gas.
  • the above reaction can be performed in the presence of a solvent, if necessary.
  • a solvent such as halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene
  • Aromatic hydrocarbons such as; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA)
  • aprotic polar solvents such as: ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane.
  • the reaction temperature for the above reaction is usually in the range of ⁇ 20 ° C. to 50 ° C., desirably in the range of 0 ° C. to room temperature, and the reaction time is usually in the range of 1 minute to 48 hours.
  • the compound according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide.
  • the range of application ranges widely from agricultural fields such as paddy fields, upland fields, orchards, mulberry fields, and non-agricultural land such as forests, farm roads, grounds, and factory sites.
  • Applicable methods include soil treatment, foliage treatment, and flooding treatment as appropriate. You can choose.
  • the compounds according to the present invention can control a wide range of undesirable plants such as annual and perennial weeds. Specifically, for example, barnyardgrass (Echinochloa crus-galli L., Echinochloa oryzicola vasing.)), Barkyard (crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr.
  • barnyardgrass Echinochloa crus-galli L., Echinochloa oryzicola vasing.
  • Barkyard crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr.
  • Firefly Cyperaceae such as); Urikawa (Japanese ribbon waparo (Sagittariapygmaea)), Omodaka (arrow-head (Sagittaria trifolia)), Heramodaka (narrowleaf waterplantain (Alisma canaliculatum)) ; Weeping (monochoria (Monochoriavaginalis)), squirrel (monochoria species (Monochoriakorsakowii)), weeds (pontederiaceae); azena (false pimpernel (Linderni a pyxidaria)), Abunome (Dopatrium junceum) psyllium weed (plantaginaceae); Weeds (lythraceae); Eelineaceae such as long stem waterwort (Elatine triandra SCHK.); Velvetleaf (Abutilon theophrastiMEDIC.), Prickly sida (Sida spinosa L.) Such
  • Convolvulaceae such as)); common lambsquarters (Chenopodium album L.), cypress (Amaran thaceae) such as broom (Amaran thaceae); common purslane (PortulacaoleraceaL.)), Such as Portulacaceae; leguminous weeds (sicklepod (Cassia obtusifolia L.)); fabaceae; common chickweed (StellariamediaL.) (Caryophyllaceae); Rubiaceae weeds such as catchweed (Galium spurium L.); Euphorbiaceae such as threeseeded copperleaf (AcalyphaaustralisL.); It is possible to control various harmful weeds such as Commelinaceae such as L.)).
  • useful crops such as corn (corn (Zea mays L.)), soybean (soybean (Glycine max Merr.)), Cotton (cotton (Gossypiumspp.)), Wheat (wheat (Triticumspp.)), Rice (rice ( Oryzasativa L.), barley (barde (Hordeum Vulgare L.)), rye (rye (Secalecereale L.)), oat (oat (Avena sativa L.)), sorghum (sorgo (Sorghum bicolor Moench)), rape (rape ( Brassicanapus L.)), sunflower (sunflower (Helianthus annuus L.)), sugar beet (suger beet (Beta Vulgaris L.)), sugar cane (suger cane (Saccharum officinarum L.)), turf (japanese lawngrass (Zoysia japonica stend))
  • the compound according to the present invention is usually mixed with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, tablets, pills, capsules (including forms packaged with water-soluble films).
  • various agricultural adjuvants powders, granules, granule wettable powders, wettable powders, tablets, pills, capsules (including forms packaged with water-soluble films).
  • Aqueous suspension, oil suspension, microemulsion formulation, suspoemulsion formulation, aqueous solvent, emulsion, solution, paste, etc. can be prepared and applied, but fits the purpose of the present invention As long as it is, it can be in any formulation form commonly used in the art.
  • Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoic acid Salt, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol S
  • adjuvants can be used by appropriately selecting one or two or more kinds without departing from the object of the present invention.
  • extenders thickeners, anti-settling agents, antifreeze agents, dispersion agents
  • dispersion agents Various commonly used adjuvants such as stabilizers, safeners, antifungal agents, foaming agents, disintegrating agents, binders and the like can also be used.
  • the compounding ratio of the compound according to the present invention and various adjuvants is 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.
  • the application rate (herbicidally effective amount) of the herbicide containing the compound according to the present invention cannot be defined unconditionally due to differences in weather conditions, soil conditions, formulation forms, types of undesirable plants targeted, application time, etc.
  • the amount of the compound according to the present invention is 0.1 to 5,000 g, preferably 0.5 to 3,000 g, more preferably 1 to 1,000 g per hectare.
  • the present invention also includes a method for controlling undesirable plants by applying such herbicides.
  • the herbicide containing the compound according to the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners and the like, and in this case, more excellent effects and activities may be exhibited.
  • Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like.
  • the mixed herbicidal composition in which the compound according to the present invention and one or more compounds as active ingredients of other herbicides are used in combination or in combination the range of the applicable herbaceous species, the timing of drug treatment, It is possible to improve the herbicidal activity and the like in a preferable direction.
  • the compound which is the active ingredient of the compound which concerns on this invention and another herbicide may mix and use it at the time of dispersion
  • the above-mentioned mixed herbicidal composition is also included in the present invention.
  • the mixing ratio between the compound according to the present invention and the compound that is an active ingredient of other herbicides cannot be defined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application time, application method, etc.
  • Other herbicides are compounded in an amount of 0.001 to 10,000 parts by weight, preferably 0.01 to 1,000 parts by weight, as an active ingredient for other herbicides.
  • the appropriate amount to be applied is 0.1 to 10,000 g, preferably 0.2 to 5,000 g, more preferably 10 to 3,000 g as the total amount of active ingredients per hectare.
  • the present invention also includes a method for controlling undesirable plants by application of such a mixed herbicidal composition.
  • Examples of the compound that is an active ingredient of other herbicides include the following compounds (generic names; some of which are included in the application for ISO). If an alkyl ester or the like is present, it is naturally included.
  • Quaternary ammonium salt compounds such as paraquat and diquat, which are said to themselves become free radicals in the plant body and generate active oxygen to show rapid herbicidal efficacy.
  • pyridazinone compounds such as norflurazon, chloridazon, metflurazon; pyrazolynate, pyrazoxifene, benzofenap, topramezone, BAS-670H, Pyrazole compounds such as pyrasulfotole; others, amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione ( sulcotrione, mesotrione, tembotrione, teboyltrione, AVH-301, KUH-110, SW-065, isoxaflutole, difenzoquat, diphen Pigment production of plants such as carotenoids such as coat methylsulfate (difenzoquat-metilsulfate), isoxachlortole, benzobicyclon, bicyclopyron, picolinafen, and biflubutamid A compound that inhibits synthesis and exhibits
  • MSMA, DSMA, CMA endothal (endothall), endothal-dipotassium, endothal sodium (endothall-sodium), endtal mono (N, N-dimethylalkylammonium) (endothall-mono ( N, N-dimethylalkylammonium)), etofumesate, sodium chlorate, pelargonic acid, nonanoic acid, fosamine, fosamine-ammonium, ipfen Carbazone (ipfencarbazone, HOK-201), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarson Acid (methylarsonic acid) , Dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate , DNOC, ferrous sulfate (flupropanate),
  • Synthesis example 1 Synthesis of 1,1,1-trifluoro-N- (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 1-1) (1) Nitrogen Under atmosphere, a solution of methyl 3-amino-2-thiophenecarboxylate (7.86 g), triethylamine (6.93 ml) and chloroform (200 ml) was cooled to 0 ° C, trifluoromethanesulfonic anhydride (8.20 ml) and chloroform (20 ml) was added dropwise over 15 minutes. The mixture was further stirred for 20 hours while raising the temperature to room temperature.
  • reaction solution was washed with water, and the aqueous layer was extracted with chloroform.
  • the organic layers were combined, washed with saturated brine, and then washed twice with 2N aqueous sodium hydroxide solution (100 ml).
  • the separated alkaline aqueous solution was acidified with concentrated hydrochloric acid and extracted with ethyl acetate.
  • the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a yellow solid (8.70 g).
  • the 1 H-NMR spectrum data of methyl 3- (trifluoromethylsulfonamido) thiophene-2-carboxylate is shown below.
  • the 1 H-NMR spectrum data of 3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid is shown below.
  • Synthesis example 2 Synthesis of isobutyl (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 1-7) 1,1,1-trifluoro -N- (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (210 mg) was dissolved in toluene (6 ml), pyridine (0.10 ml) and chloroformate Isobutyl (0.16 ml) was added and stirred at room temperature for 17 hours.
  • Synthesis example 3 Synthesis of 1,1,1-trifluoro-N- (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 13-1) (1) Under a nitrogen atmosphere, a solution of methyl 3-amino-4-methylthiophene-2-carboxylate (5.41 g), triethylamine (5.26 ml) and chloroform (200 ml) was cooled to ⁇ 4 ° C. to obtain trifluoromethanesulfone. A mixed solution of acid anhydride (10.7 g) and chloroform (20 ml) was added dropwise over 25 minutes.
  • the mixture was further stirred for 1 hour while cooling with ice, and water was added to stop the reaction.
  • the aqueous layer was extracted with chloroform.
  • the organic layers were combined and washed twice with 2N aqueous sodium hydroxide solution (100 ml).
  • the aqueous alkaline solution was separated and stirred at reflux for 20 minutes. After cooling to room temperature, it was acidified with concentrated hydrochloric acid.
  • the suspension was stirred while cooling with ice, and the resulting solid was filtered, washed with water, and then dried under reduced pressure to give 4-methyl-3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid.
  • the acid was obtained as a pale pink solid (3.09 g).
  • Synthesis example 4 Synthesis of ethyl (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 13-3) 1,1, 1-trifluoro-N- (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (785 mg) was dissolved in toluene (10 ml), Pyridine (0.36 ml) and ethyl chloroformate (0.42 ml) were added, and the mixture was stirred at room temperature for 2 hours.
  • Synthesis example 6 Synthesis of ethyl (2-((2-thioxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 1-48) 1,1,1-Tri Fluoro-N- (2-((2-thioxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (163 mg) was dissolved in toluene (3 ml) and pyridine (0.10 ml) was dissolved. Ethyl chloroformate (0.10 ml) was added and stirred at room temperature for 2 hours.
  • Synthesis example 7 Synthesis of 1,1,1-trifluoro-N- (2-((3-oxomorpholino) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 6-1) (1) Hydrogen in a nitrogen atmosphere A solution of sodium halide (60 wt%, 1.2 g) and dioxane (25 ml) was cooled to 0 ° C., ethanolamine (1.5 ml) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0 ° C., ethyl chloroacetate (2.7 ml) was added, and the mixture was stirred at room temperature for 30 min. After cooling the reaction solution, the solid was removed by filtration.
  • Synthesis example 8 Synthesis of ethyl (2-((3-oxomorpholino) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 6-3) 1,1,1-trifluoro-N- ( 2-((3-oxomorpholino) methyl) thiophen-3-yl) methanesulfonamide (150 mg) is dissolved in toluene (4.4 ml) and pyridine (0.06 ml) and ethyl chloroformate (0.07 ml) are added. And stirred at room temperature for 15 hours.
  • the mixture was stirred for 1 hour under reflux, and after cooling, sodium borohydride (4.38 g) was added under ice cooling, followed by stirring at room temperature for 2 hours.
  • a 3N aqueous hydrochloric acid solution was added and the mixture was stirred for 10 minutes, followed by extraction with ethyl acetate, and the aqueous layer was further washed with ethyl acetate.
  • the aqueous layer was made basic by adding 6N aqueous sodium hydroxide solution, and extracted with ethyl acetate.
  • N- (2-((6,6-Dimethyl-2-oxo-1,3-oxazinan-3-yl) methyl) thiophen-3-yl) -1,1,1-trifluoromethanesulfonamide 0.14 g was dissolved in toluene (5.0 ml), pyridine (59.3 mg) and ethyl chloroformate (81.4 mg) were added, and the mixture was stirred at room temperature for 2 hours. After 2 N hydrochloric acid aqueous solution was added to stop the reaction, the aqueous layer was extracted with ethyl acetate.
  • Tables 1 to 13 typical examples of the compounds of the present invention are listed in Tables 1 to 13. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • Tables 1 to 13 the numerical values described in the physical properties column represent melting points (° C.), and for compounds described as NMR, the 1 H-NMR spectrum data and the solvent used for the measurement are shown in Table 14. I will give you.
  • Tables 1 to 14 No. indicates the compound number.
  • Me is a methyl group
  • Et is an ethyl group
  • n-Pr is a normal propyl group
  • i-Pr is an isopropyl group
  • c-Pr is a cyclopropyl group
  • n-Bu is a normal butyl group.
  • S-Bu is a secondary butyl group
  • i-Bu is an isobutyl group
  • t-Bu is a tertiary butyl group
  • c-Hex is a cyclohexyl group
  • c-Bu is a cyclobutyl group
  • Ph is a phenyl group.
  • C O each represents a carbonyl group.
  • 3-CF 3 Ph represents a phenyl group substituted with CF 3 at the 3-position, and other similar descriptions are based on this.
  • E-1 to E-12 each represent the following structure.
  • Test example 1 A field crop soil was packed in a 1 / 170,000 hectare pot and seeds of various plants were sown. After that, the plant had a certain leaf age ((1) barnyardgrass (Echinochloa crus-galli L.); 0.5-3.0 leaf stage, (2) crabgrass (Digitaria sanguinalis L.)); 0.5-3.0 leaf stage , (3) Green foxtail (Setariaviridis L.); 1.0-3.5 leaves, (4) Red root pigweed (Amaranthusretroflexus L.); 0.2-2.5 leaves, (5) American prickly sida (prickly sida ( Sida spinosa L.)); cotyledon-2.0 leaf stage, (6) velvetleaf (Abutilon theophrastiMEDIC.); 0.2-2.0 leaf stage, (7) rice (rice (Oryza sativa L.)); 0.5-2.5 leaf (8) Corn (Zea maysL.); 2.0-3.5 leaf stage, (9) Wheat (Triticum spp.
  • the compound according to the present invention was prepared according to the usual formulation method Wettable powder or emulsion is weighed to the prescribed active ingredient amount and diluted in water equivalent to 500 liters per hectare (agricultural spreading agent (xalino: manufactured by Nippon Agricultural Chemicals) containing 0.1% by volume) It was. The prepared spray was treated with a small spray.
  • Test example 2 Field crop soil is packed in 1 / 170,000 hectare pot or 1 / 300,000 hectare pot, and various plants (barnyardgrass (Echinochloacrus-galli L.)), barkyard (crabgrass (Digitariasanguinalis L.)), green foxtail (Setariaviridis L.
  • a wettable powder or emulsion prepared according to the usual formulation method of the compound according to the present invention is weighed to a predetermined active ingredient amount, and diluted to 500 liters or 1000 liters of water per hectare.
  • the soil was treated with a small spray.
  • Test example 3 Paddy soil was packed in a 1 / 1,000,000 hectare pot, seeds of barnyardgrass (Echinochloa oryzicola vasing.) And firefly (Japanese bulrush (Scirpus juncoides)) were sown and lightly soiled on top. After that, it was left in a greenhouse at a depth of 0.5 to 1 cm, and a tuber of Urikawa (Japanese ribbon waparo (Sagittaria pygmaea)) was planted the next day.
  • the compound according to the present invention was prepared according to a conventional formulation method or a wettable powder or emulsion.
  • the aqueous diluted solution was uniformly dropped with a pipette so as to obtain a predetermined active ingredient amount.
  • paddy soil is packed in a 1 / 1,000,000 hectare pot, and the paddy depth is 3-4 cm.
  • rice rice (Oryza sativa L.)) (variety: Nipponbare) is transplanted at a depth of 3 cm. Transplanted.
  • the compound according to the present invention was treated in the same manner as described above.
  • Formulation example 1 (1) Compound according to the present invention 75 parts by weight (2) Geropone T-77 (trade name; manufactured by Rhone-Poulenc) 14.5 parts by weight (3) NaCl 10 parts by weight (4) dextrin 0.5 parts by weight or more Each of the components (1) to (4) is put into a high-speed mixing fine granulator, 20% water is further added thereto, and granulated and dried to obtain a granulated wettable powder.
  • Formulation example 2 (1) Kaolin 78 parts by weight (2) Labelin FAN (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 2 parts by weight (3) Solpol 5039 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 5 parts by weight (4 ) Carplex (trade name; manufactured by DSL Japan Co., Ltd.) 15 parts by weight or more of the mixture of the components (1) to (4) and the compound according to the present invention are mixed at a weight ratio of 9: 1. A Japanese medicine is obtained.
  • Formulation example 3 (1) High filler No. 10 (trade name; manufactured by Matsumura Sangyo Co., Ltd.) 33 parts by weight (2) Solpol 5050 (trade name; manufactured by Toho Chemical Co., Ltd.) 3 parts by weight (3) Solpol 5073 (trade name; Toho Chemical Industries, Ltd.) 4 parts by weight (4) Compound according to the present invention 60 parts by weight or more of each component (1) to (4) is mixed to obtain a wettable powder.
  • Formulation example 4 (1) Compound according to the present invention 4 parts by weight (2) Bentonite 30 parts by weight (3) Calcium carbonate 61.5 parts by weight (4) Toxanone GR-31A (trade name; manufactured by Sanyo Chemical Industries, Ltd.) 3 parts by weight (5) Lignin sulfonic acid calcium salt 1.5 parts by weight Pre-ground (1), (2) and (3) are mixed, and (4), (5) and water are added and mixed there. Extrude granulate. Then, a granule is obtained by drying and sizing.
  • Formulation example 5 (1) Compound according to the present invention 30 parts by weight (2) Siegrite (trade name; manufactured by Siegrite Co., Ltd.) 60 parts by weight (3) New Calgen WG-1 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 Part by weight (4) New Calgen FS-7 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight After mixing (1), (2) and (3) above and passing through a pulverizer, (4) After kneading and extruding granulation. Thereafter, the wettable powder is obtained by drying and sizing.
  • Siegrite trade name; manufactured by Siegrite Co., Ltd.
  • New Calgen WG-1 trade name; manufactured by Takemoto Yushi Co., Ltd.
  • New Calgen FS-7 trade name; manufactured by Takemoto Yushi Co., Ltd.
  • Formulation Example 6 (1) Compound according to the present invention 28 parts by weight (2) Sopropol FL (trade name; manufactured by Rhone-Poulenc) 2 parts by weight (3) Solpol 355 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 1 part by weight ( 4) IP solvent 1620 (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) 32 parts by weight (5) ethylene glycol 6 parts by weight (6) water 31 parts by weight or more of the components (1) to (6) were mixed. An aqueous suspension is obtained by pulverization using a wet pulverizer (Dyno mill).
  • the heteroarylsulfonamide compound or a salt thereof according to the present invention realizes a significant improvement in herbicidal activity against undesirable plants as compared to similar conventional compounds. In addition, it has high safety for crops. Therefore, the heteroaryl sulfonamide compound or a salt thereof according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide.
  • the range of application ranges widely from agricultural fields such as paddy fields, upland fields, orchards, mulberry fields, and non-agricultural land such as forests, farm roads, grounds, and factory sites. Applicable methods include soil treatment, foliage treatment, and flooding treatment as appropriate. You can choose.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Provided is a novel herbicide having excellent herbicidal activity on undesirable plants. The heteroaryl sulfonamide compound or salt thereof has a structure represented by general formula (I): [in the formula, A is an oxygen atom, sulfur atom, SO, SO2, or CR8R9; W is an oxygen atom or sulfur atom; Z is an oxygen atom, sulfur atom, or CR10R11; m is 0, 1, or 2; n is 0, 1, or 2; where 0≦n+m≦3; q is 0, 1, or 2; R1 is a haloalkyl; R2 is a hydrogen atom, alkoxycarbonyl, or the like; R3 is a halogen atom, alkyl, cycloalkyl optionally substituted by an alkyl, haloalkyl, halocycloalkyl, alkylsulfonyl, alkylcarbonyl, phenyl optionally substituted by Y, cyano, or the like; R4, R5, R6, R7, R8, R9, R10, and R11 may be the same or different and are a hydrogen atom, halogen atom, alkyl, or the like].

Description

ヘテロアリールスルホンアミド系化合物又はその塩Heteroaryl sulfonamide compound or salt thereof

　本発明は、除草剤の有効成分として有用な新規のヘテロアリールスルホンアミド系化合物又はその塩、並びにそれらを含有する除草剤に関する。 The present invention relates to a novel heteroarylsulfonamide compound or salt thereof useful as an active ingredient of a herbicide, and a herbicide containing them.

　下記特許文献１、特許文献２、特許文献３及び特許文献４には、一定の構造を有するハロアルキルスルホンアニリド誘導体が開示されている。しかしながら、それらには後述する一般式（I）で表されるヘテロアリールスルホンアミド系化合物は具体的には開示されていない。 The following Patent Document 1, Patent Document 2, Patent Document 3, and Patent Document 4 disclose haloalkylsulfonanilide derivatives having a certain structure. However, they do not specifically disclose the heteroarylsulfonamide compounds represented by the general formula (I) described later.

日本国公開特許公報第２００６－２６５２４０号Japanese Published Patent Publication No. 2006-265240 日本国公開特許公報第２００８－１４３８９５号Japanese Patent Publication No. 2008-143895 国際公開公報ＷＯ２０１０／０２６９８９号International Publication No. WO2010 / 026989 国際公開公報ＷＯ２０１０／１１９９０６号International Publication No. WO2010 / 119906

　従来から、雑草を防除する作業の省力化や農園芸用作物の生産性向上を図る為、雑草に対して優れた除草性能を有し、且つ栽培作物に対する安全性を有する除草剤が所望されている。これからの新しい除草剤の開発においては、その施用薬量を低く抑えつつも所望の除草効果を発揮することができる化合物の創出が希求されている。また、実用的な残効性を示しつつも必要以上に土壌中に残留したり、雨水などにより施用箇所以外の土壌へ有効成分が流出するなどして環境へ悪影響を及ぼしたりする恐れの少ない化合物の創出が希求されている。さらには、高い動物安全性を備えた化合物の創出が望まれている。しかし、そのような目的に適した新規化合物の探索は試行錯誤に頼っている。 Conventionally, there has been a demand for a herbicide that has excellent herbicidal performance against weeds and safety for cultivated crops in order to save labor in controlling weeds and improve productivity of agricultural and horticultural crops. Yes. In the development of new herbicides in the future, there is a demand for the creation of compounds that can exhibit the desired herbicidal effect while keeping the amount of applied herbage low. In addition, compounds that have practical residual effects but are less likely to remain in the soil than necessary or have a negative impact on the environment due to the outflow of active ingredients to soils other than the application site due to rainwater, etc. Creation of is demanded. Furthermore, creation of a compound with high animal safety is desired. However, the search for new compounds suitable for such purposes relies on trial and error.

　本発明者らは、前記課題を解決するような、より優れた除草剤を見出すべく種々検討した。その結果、新規なヘテロアリールスルホンアミド系化合物が、低薬量で多様な雑草に高い除草効果を示し、なお且つ各種有用作物に高い安全性を示すことを見出し、本発明を完成した。 The present inventors have made various studies in order to find a more excellent herbicide that can solve the above-mentioned problems. As a result, the present inventors have found that the novel heteroarylsulfonamide-based compound exhibits a high herbicidal effect on various weeds with a low dosage, and also exhibits high safety for various useful crops, thereby completing the present invention.

　即ち本発明は、一般式（I）： That is, the present invention relates to the general formula (I):

Figure JPOXMLDOC01-appb-C000002
Figure JPOXMLDOC01-appb-C000002

〔式中、Aは酸素原子、硫黄原子、SO、SO2又はCR8R9であり；Wは酸素原子又は硫黄原子であり；Zは酸素原子、硫黄原子又はCR10R11であり；mは0、１又は2であり；nは0、１又は2であり；但し、0≦n+m≦3であり；qは0、１又は2であり；R1はハロC1－C6アルキルであり；R2は水素原子、C1－C12アルコキシカルボニル、C1－C12アルキルカルボニル、ハロC1－C6アルキルカルボニル、シクロC3-C6アルキルカルボニル、シクロC3-C6アルキルC1-C6アルキルカルボニル、C2-C6アルケニルカルボニル、Yで置換されてもよいフェニルC2-C6アルケニルカルボニル、Yで置換されてもよいフェニルカルボニル、Yで置換されてもよい複素環カルボニル、ハロC1－C12アルコキシカルボニル、C1-C6アルキルで置換されてもよいシクロC3-C6アルコキシカルボニル、C2-C6アルケニルオキシカルボニル、ハロC2-C6アルケニルオキシカルボニル、C2-C6アルキニルオキシカルボニル、C1-C6アルコキシC1-C6アルコキシカルボニル、C1-C6アルキルチオC1-C6アルコキシカルボニル、C1-C6アルキルスルフィニルC1-C6アルコキシカルボニル、C1-C6アルキルスルホニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルハロC1-C6アルコキシカルボニル、Yで置換されてもよいフェノキシカルボニル、Yで置換されてもよいフェノキシC1-C6アルキルカルボニル、C1-C6アルキルチオカルボニル、ハロC1-C6アルキルチオカルボニル、モノC1-C6アルキルアミノカルボニル、モノ（ハロC1-C6アルキル）アミノカルボニル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニル、ジ（ハロC1-C6アルキル）アミノカルボニル、C1-C6アルコキシC1-C6アルキルカルボニル、C1-C6アルコキシカルボニルC1-C6アルキルカルボニル、C1-C6アルコキシオキサリル、C1-C6アルキルスルホニル、ハロC1-C6アルキルスルホニル、Yで置換されてもよいフェニルスルホニル、アミノスルホニル、モノC1-C6アルキルアミノスルホニル、ジC1-C6アルキルアミノスルホニル、Yで置換されてもよい複素環スルホニル、シクロC3-C6アルキルスルホニル、C1-C6アルキル、ハロC1-C6アルキル、C2-C6アルケニル、ハロC2-C6アルケニル、C2-C6アルキニル、ハロC2-C6アルキニル、Yで置換されてもよいフェニルC1-C6アルキル、Yで置換されてもよいフェニルカルボニルC1-C6アルキル、C1-C6アルコキシC1-C6アルキル、ハロC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシC1-C6アルコキシC1-C6アルキル、トリC1-C6アルキルシリルC1-C6アルコキシC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルC1-C6アルキル、C1-C6アルキルカルボニルオキシC1-C6アルキル、シクロC3-C6アルキルカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルキル、Yで置換されてもよい複素環カルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルオキシC1-C6アルキル、シクロC3-C6アルコキシカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェノキシカルボニルオキシC1-C6アルキル、モノC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいN-C1-C6アルキル-N-フェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルチオC1-C6アルキル、Yで置換されてもよいフェニルスルフィニルC1-C6アルキル、Yで置換されてもよいフェニルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルチオC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルホニルC1-C6アルキル、C1-C6アルキルチオC1-C6アルキル、ハロC1-C6アルキルチオC1-C6アルキル、C1-C6アルキルスルフィニルC1-C6アルキル、C1-C6アルキルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルフィニルC1-C6アルキル、チオシアナトC1-C6アルキル、シアノC1-C6アルキル、Yで置換されてもよい複素環C1-C6アルキル、C1-C6アルキルカルボニルC1-C6アルキル又はシアノであり；R3はハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、C1－C6アルキルカルボニル、Yで置換されてもよいフェニル又はシアノであり；R4、R5、R6、R7、R8、R9、R10及びR11は、それぞれ同一又は異なってもよく、水素原子、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C3－C6シクロアルキルC1－C6アルキル、Yで置換されてもよいフェニル、Yで置換されてもよいフェニルC1－C6アルキル、C1－C6アルキルカルボニルオキシ、カルボキシル、C1－C6アルコキシカルボニル、ハロC1－C6アルコキシカルボニル、水酸基又はシアノであり；R4とR5、R6とR7、R8とR9及びR10とR11は各々互いに結合して、任意に置換されてもよい3～7員環を形成することができ、当該3～7員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく、或いは、オレフィン、カルボニル又はチオカルボニルを形成することができ；R4、R5、R6、R7、R8、R9、R10及びR11は、各々が結合する炭素原子とは別の炭素原子上の、任意のR4、R5、R6、R7、R8、R9、 R10又はR11と結合して、任意に置換されてもよい3～8員環を形成することができ、当該3～8員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく；R4、R5、R6、R7、R8、R9、R10及びR11は、それらが結合する炭素原子と隣り合った炭素原子上の任意のR4、R5、R6、R7、R8、R9、R10又はR11と結合することができ；Yは、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルコキシ、ハロC1－C6アルコキシ、C1－C6アルキルチオ、ハロC1－C6アルキルチオ、C1－C6アルキルスルフィニル、ハロC1－C6アルキルスルフィニル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、カルボキシル、C1－C6アルキルカルボニル、ハロC1－C6アルキルカルボニル、C1－C6アルコキシカルボニル、ハロC1－C6アルコキシ
カルボニル、アミノ、モノ（C1－C6アルキル）アミノ、モノ（ハロC1－C6アルキル）アミノ、ジ（C1－C6アルキル）アミノ、ジ（ハロC1－C6アルキル）アミノ、シアノ、ニトロ又は水酸基であり；前記複素環は、チエニル、フリル、ピロリル、オキサゾリル、イソオキサゾリル、イソオキサゾリニル、チアゾリル、イソチアゾリル、ピラゾリル、イミダソリル、1,3,4-オキサジアゾリル、1,2,4-オキサジアゾリル、1,3,4-チアジアゾリル、1,2,4－チアジアゾリル、1,2,4－トリアゾリル、1,2,3－トリアゾリル、1,2,3－チアジアゾリル、1，2，3，4-テトラゾリル、ピリジル、ピリミジル、ピラジニル、ピリダジニル、1,3,5-トリアジニル、1,2,4-トリアジニル、ベンゾチエニル、ベンゾフリル、インドリル、ベンゾチアゾリル、ベンゾイミダゾリル、ベンゾイソオキサゾリル、ベンゾイソチアゾリル、インダゾリル、ベンゾオキサゾリル、キノリル、イソキノリル、キノキサリニル、フタラジニル、シンノリニル、キナゾリニル、イミダゾリニル、イミダゾリジニル、ピラゾリニル又はピラゾリジニルである〕
で表されるヘテロアリールスルホンアミド系化合物又はその塩に関する。 [Wherein A is an oxygen atom, sulfur atom, SO, SO 2 or CR 8 R 9 ; W is an oxygen atom or sulfur atom; Z is an oxygen atom, sulfur atom or CR 10 R 11 ; m Is 0, 1 or 2; n is 0, 1 or 2; provided that 0 ≦ n + m ≦ 3; q is 0, 1 or 2; R 1 is haloC 1 -C 6 R 2 is a hydrogen atom, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo C 3 -C 6 alkylcarbonyl, cyclo C 3 -C 6 Alkyl C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, phenyl C 2 -C 6 alkenylcarbonyl optionally substituted with Y, phenylcarbonyl optionally substituted with Y, optionally substituted with Y heterocyclylcarbonyl, halo C 1 -C 12 alkoxycarbonyl, C 1 -C 6 alkyl substituted cyclo C 3 which may be -C 6 alkoxycarbonyl C 2 -C 6 alkenyloxycarbonyl, halo C 2 -C 6 alkenyloxycarbonyl, C 2 -C 6 alkynyloxy-carbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkoxycarbonyl, phenyl C 1 -C 6 alkoxy optionally substituted by Y carbonyl, Y which may be substituted Feniruharo C 1 -C 6 alkoxycarbonyl, good phenoxycarbonyl which may be substituted by Y, Y-substituted which may phenoxy C 1 -C six alkylcarbonyl, C 1 -C 6 alkylthio Carbonyl, halo C 1 -C 6 alkylthiocarbonyl, mono C 1 -C 6 alkylaminocarbonyl, mono (halo C 1 -C 6 alkyl) aminocarbonyl, two C 1 -C on nitrogen atoms Di-C 1 -C 6 alkylaminocarbonyl, di (halo C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkoxy C 1-which 6 alkyl may combine with each other to form a 3- to 8-membered ring C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxyoxalyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, optionally substituted with Y Phenylsulfonyl, aminosulfonyl, mono C 1 -C 6 alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, heterocyclic sulfonyl optionally substituted with Y, cyclo C 3 -C 6 alkylsulfonyl, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halo C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo C 2 -C 6 alkynyl, optionally substituted with Y Phenyl C 1 -C 6 alkyl, optionally substituted with Y Phenylcarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halo C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl, tri-C 1 -C 6 alkylsilyl C 1 -C 6 alkoxy C 1 -C 6 alkyl, phenyl optionally substituted with Y C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1- C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, which may be substituted by Y phenyl Carbonyloxy C 1 -C 6 alkyl, heterocyclic carbonyloxy C 1 -C 6 alkyl optionally substituted with Y, phenylcarbonyloxy C 1 -C 6 alkoxy C 1 -C 6 alkyl optionally substituted with Y, C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkoxycarbonyloxy C 1 -C 6 Alkyl, phenoxycarbonyloxy C 1 -C 6 alkyl optionally substituted with Y, mono C 1 -C 6 alkylaminocarbonyloxy C 1 -C 6 alkyl, two C 1 -C 6 alkyl on the nitrogen atom coupled to 3- to 8-membered ring formed is also good di C 1 -C six alkylaminocarbonyloxy C 1 -C 6 alkyl, Y-substituted phenyl aminocarbonyl-oxy C 1 -C 6 alkyl, Y NC 1 -C 6 alkyl optionally substituted with N-phenylaminocarbonyloxy C 1 -C 6 alkyl, phenylthio C 1 -C 6 alkyl optionally substituted with Y, phenylsulfinyl optionally substituted with Y C 1 -C 6 alkyl, phenylsulfonyl C 1 -C 6 alkyl optionally substituted with Y, phenyl C 1 -C 6 alkylthio optionally substituted with Y C 1 -C 6 alkyl, optionally substituted with Y phenyl C 1 -C 6 alkylsulfonyl C 1 -C 6 al Le, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halo C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl, optionally substituted with Y phenyl C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl, thiocyanato C 1 -C 6 alkyl, cyano C 1 -C 6 alkyl, substituted with Y A heterocycle C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl or cyano; R 3 is a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted with C 1 -C 6 alkyl C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl Be phenyl or cyano be substituted by Y; R 4, R 5, R 6, R 7, R 8, R 9, R 10 and R 11 may be the same or different, a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted C 3 may be -C 6 cycloalkyl, halo C 1 -C 6 alkyl Halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, phenyl optionally substituted by Y, Y Phenyl C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, carboxyl, C 1 -C 6 alkoxycarbonyl, halo C 1 -C 6 alkoxycarbonyl, hydroxyl or cyano optionally substituted with R 4 ; and R 5, R 6 and R 7, R 8 and R 9 and R 10 and R 11 are each coupled to one another, it may be optionally substituted 3 It is possible to form a 7-membered ring, the 3-7 membered ring is an oxygen atom, a sulfur atom or a nitrogen atom (nitrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 May contain 1 or 2 heteroatoms selected from alkynyl or C 3 -C 6 cycloalkyl), or may form an olefin, carbonyl or thiocarbonyl; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R 6 , R on a carbon atom different from the carbon atom to which each is bonded. 7 , R 8 , R 9 , R 10 or R 11 can be combined to form an optionally substituted 3- to 8-membered ring, which is an oxygen atom, sulfur atom or nitrogen atom (the nitrogen atom may be substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl, by C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl) May contain 1 or 2 heteroatoms et selected; R 4, R 5, R 6, R 7, R 8, R 9, R 10 and R 11, adjacent the carbon atom to which they are attached Can be attached to any R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 on the combined carbon atom; Y is a halogen atom, C 1 -C 6 alkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C may be substituted with alkyl C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl Halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, carboxyl, C 1 -C 6 alkylcarbonyl Le, halo C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo C 1 -C 6 alkoxycarbonyl, amino, mono (C 1 -C 6 alkyl) amino, mono (halo C 1 -C 6 alkyl ) Amino, di (C 1 -C 6 alkyl) amino, di (halo C 1 -C 6 alkyl) amino, cyano, nitro or hydroxyl; the heterocycle is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, iso Oxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4- Triazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4- Triazinyl, Nzothienyl, benzofuryl, indolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, imidazolinyl, imidazolidinyl, pyrazolidinyl, pyrazolidinyl, pyrazolinyl
And a salt thereof.

　また本発明は、前記一般式（I）のヘテロアリールスルホンアミド系化合物又はその塩を有効成分として含有する除草剤、当該化合物又はその塩の除草有効量を、望ましくない植物又はそれが生育する場所に施用し、望ましくない植物を防除又はその生育を抑制する方法に関する。 The present invention also provides a herbicide containing the heteroarylsulfonamide compound of general formula (I) or a salt thereof as an active ingredient, an herbicidally effective amount of the compound or a salt thereof, an undesirable plant or a place where it grows. The present invention relates to a method for controlling undesired plants or suppressing their growth.

　前記一般式（I）のヘテロアリールスルホンアミド系化合物又はその塩は、類似する従来化合物に比して望ましくない植物（雑草）への著しい除草活性の向上を実現する。また、作物への高い安全性を有する。 The heteroarylsulfonamide compound of the general formula (I) or a salt thereof realizes a significant improvement in herbicidal activity against undesirable plants (weeds) as compared to similar conventional compounds. In addition, it has high safety for crops.

　前記一般式（I）中のハロゲン原子又は置換基としてのハロゲンとしては、フッ素、塩素、臭素又はヨウ素の各原子が挙げられる。置換基としてのハロゲン原子の数は１又は２以上であってよく、２以上の場合、各ハロゲン原子は同一でも相異なってもよい。また、ハロゲン原子の置換位置は何れの位置でもよい。 Examples of the halogen atom or the halogen as a substituent in the general formula (I) include fluorine, chlorine, bromine and iodine atoms. The number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.

　一般式（I）中のアルキル又はアルキル部分としては、例えば、メチル、エチル、ノルマルプロピル、イソプロピル、ノルマルブチル、イソブチル、セカンダリーブチル、ターシャリーブチル、ノルマルペンチル、ネオペンチル、ノルマルヘキシルのような直鎖又は分岐鎖状のC１-C１２の基が挙げられる。また、置換基の位置によっては、C１-C6のものであってもよい。 Examples of the alkyl or alkyl moiety in the general formula (I) include a straight chain such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, neopentyl, and normal hexyl. Examples include a branched C 1 -C 12 group. Depending on the position of the substituent, it may be C 1 -C 6 .

　一般式（I）中のアルコキシ又はアルコキシ部分としては、例えば、メトキシ、エトキシ、プロポキシ、イソプロポキシ、ブトキシ、ペンチルオキシ、ヘキシルオキシ、ドデシルオキシ等のような直鎖又は分岐鎖状のC１-C１２の基が挙げられる。また、置換基の位置によっては、C１-C6のものであってもよい。 Examples of the alkoxy or alkoxy moiety in the general formula (I) include linear or branched C 1 -C such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, pentyloxy, hexyloxy, dodecyloxy and the like. There are 12 groups. Depending on the position of the substituent, it may be C 1 -C 6 .

　一般式（I）中のアルケニル又はアルケニル部分としては、例えば、ビニル、１－プロペニル、２－プロペニル、イソプロペニル、２－メチル－１－プロペニル、１－メチル－１－プロペニル、２－メチル－２－プロペニル、１－メチル－２－プロペニル、１－ブテニル、２－ブテニル、３－ブテニル、１－ペンテニル、２－ペンテニル、２－メチル－２－ブテニル、１－ヘキセニル、２,３－ジメチル－２－ブテニルのような直鎖又は分岐鎖状のC２-C６の基が挙げられる。 Examples of the alkenyl or alkenyl moiety in the general formula (I) include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl and 2-methyl-2. -Propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3-dimethyl-2 -Linear or branched C 2 -C 6 groups such as butenyl.

　一般式（I）中のアルキニル又はアルキニル部分としては、例えば、エチニル、１－プロピニル、２－プロピニル、１－ブチニル、２－ブチニル、３－ブチニル、１－メチル－２－プロピニル、２－メチル－３－ブチニル、１－ヘキシニル、２－ヘキシニル、３－ヘキシニル、４－ヘキシニル、５－ヘキシニルのような直鎖又は分岐鎖状のC２-C６の基が挙げられる。 Examples of the alkynyl or alkynyl moiety in the general formula (I) include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl- Examples thereof include linear or branched C 2 -C 6 groups such as 3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl.

　一般式（I）中のシクロアルキル又はシクロアルキル部分としては、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシルのようなC３-C６の基が挙げられる。 Examples of the cycloalkyl or cycloalkyl moiety in the general formula (I) include C 3 -C 6 groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

　一般式（I）中のシクロアルコキシ部分としては、（シクロアルキル）－Ｏ－基を示し、例えば、シクロプロピルオキシ、シクロブチルオキシ、シクロペンチルオキシ、シクロヘキシルオキシのようなC３-C６の基が挙げられる。 The cycloalkoxy moiety in the general formula (I) represents a (cycloalkyl) -O— group, for example, a C 3 -C 6 group such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, etc. Can be mentioned.

　一般式（I）中の「C１-C６アルキルカルボニル」又は「C１-C６アルキルカルボニル部分」は、前記のC１-C６アルキル基とカルボニル基が結合した（C１-C６アルキル）－Ｃ（＝Ｏ）－基を示し、例えば、アセチル、プロピオニル、イソプロピオニル、ブチリル、ピバロイル等のような直鎖又は分岐鎖状で炭素数が２から７の脂肪族カルボン酸から誘導されるアルキルカルボニル基が挙げられる。 “C 1 -C 6 alkylcarbonyl” or “C 1 -C 6 alkylcarbonyl moiety” in the general formula (I) is a compound in which the C 1 -C 6 alkyl group is bonded to a carbonyl group (C 1 -C 6 Alkyl) -C (═O) — group, derived from a linear or branched aliphatic carboxylic acid having 2 to 7 carbon atoms, such as acetyl, propionyl, isopropionyl, butyryl, pivaloyl, etc. An alkylcarbonyl group.

　一般式（I）中、R2に含まれる「C１-C１２アルキルカルボニル」は、前記のC１-C１２アルキル基とカルボニル基が結合した（C１-C１２アルキル）－Ｃ（＝Ｏ）－基を示し、例えば、アセチル、プロピオニル、イソプロピオニル、ブチリル、ピバロイル、デカノイル、ドデカノイル等のような直鎖又は分岐鎖状で炭素数が２から１３の脂肪族カルボン酸から誘導されるアルキルカルボニル基が挙げられる。 In the formula (I), "C 1 -C 12 alkylcarbonyl" included in R 2, C 1 -C 12 alkyl group and a carbonyl group of the bound (C 1 -C 12 alkyl) -C (= O) -groups, for example alkyls derived from linear or branched aliphatic carboxylic acids having 2 to 13 carbon atoms such as acetyl, propionyl, isopropionyl, butyryl, pivaloyl, decanoyl, dodecanoyl and the like A carbonyl group is mentioned.

　一般式（I）中の「C２-C６アルケニルカルボニル」又は「C２-C６アルケニルカルボニル部分」は、前記のC２-C６アルケニル基とカルボニル基が結合した（C２-C６アルケニル）－Ｃ（＝Ｏ）－基を示し、例えば、アクリロイル、クロトノイル、メタクリロイル、２－メチル－２－ブテノイル等が挙げられる。 “C 2 -C 6 alkenylcarbonyl” or “C 2 -C 6 alkenylcarbonyl moiety” in the general formula (I) is a compound in which the C 2 -C 6 alkenyl group and the carbonyl group are bonded (C 2 -C 6 Alkenyl) -C (═O) — group such as acryloyl, crotonoyl, methacryloyl, 2-methyl-2-butenoyl and the like.

　一般式（I）中の「シクロC３-C６アルキルカルボニル」又は「C３-C６シクロアルキルカルボニル部分」は、前記のシクロC３-C６アルキル基とカルボニル基が結合した（C３-C６シクロアルキル）－Ｃ（＝Ｏ）－基を示し、例えば、シクロプロパンカルボニル、シクロブタンカルボニル、シクロペンタンカルボニル、シクロヘキサンカルボニルのような基が挙げられる。 “CycloC 3 -C 6 alkylcarbonyl” or “C 3 -C 6 cycloalkylcarbonyl moiety” in formula (I) is a compound in which the above-mentioned cyclo C 3 -C 6 alkyl group and a carbonyl group are bonded (C 3 -C 6 cycloalkyl) -C (═O) — group, for example, groups such as cyclopropanecarbonyl, cyclobutanecarbonyl, cyclopentanecarbonyl, cyclohexanecarbonyl and the like.

　一般式（I）中の「Yで置換されてもよい」とは、Yで置換される場合は、Yが1以上であってもよいことを表す。 In the general formula (I), “may be substituted with Y” means that when Y is substituted, Y may be 1 or more.

　一般式（I）中の「C１-C６アルキルで置換されてもよい」とは、C１-C６アルキルで置換される場合は、C１-C６アルキルが１以上であってもよいことを表す。 In the general formula (I), “may be substituted with C 1 -C 6 alkyl” means that when C 1 -C 6 alkyl is substituted, C 1 -C 6 alkyl is 1 or more. Represents good.

　一般式（I）中の「窒素原子上の２つのC１-C６アルキルが互いに結合して３～８員環を形成してもよいジC１-C６アルキルアミノカルボニルオキシC１-C６アルキル」とは、例えば、次のような構造が挙げられる。 General formula (I) 2 two C 1 -C 6 alkyl bond to 3-8 membered ring formed is optionally di-C 1 -C 6 alkylaminocarbonyloxy C 1 -C one another on "nitrogen atom in Examples of “ 6 alkyl” include the following structures.

Figure JPOXMLDOC01-appb-C000003
Figure JPOXMLDOC01-appb-C000003

一般式（I）中の「窒素原子上の２つのC１-C６アルキルが互いに結合して３～８員環を形成してもよいジC１-C６アルキルアミノカルボニル」とは、例えば、次のような構造が挙げられる。 The “di-C 1 -C 6 alkylaminocarbonyl in which two C 1 -C 6 alkyls on the nitrogen atom may be bonded to each other to form a 3- to 8-membered ring” in the general formula (I) is, for example, The following structures are mentioned.

Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004

　一般式（I）中、R4とR5、R6とR7、R8とR9及びR10とR11は各々互いに結合して、任意に置換されてもよい3～7員環を形成することができ、当該3～7員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよい。具体的には、例えば、R4、R5、R6、R7、R8、R9、R10又はR11の各々が結合する炭素とともに、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、エポキシ、テトラヒドロフラン、ピペリジンなどを形成することができる。 In the general formula (I), R 4 and R 5 , R 6 and R 7 , R 8 and R 9 and R 10 and R 11 are bonded to each other to form an optionally substituted 3- to 7-membered ring. The 3- to 7-membered ring can be an oxygen atom, a sulfur atom or a nitrogen atom (wherein the nitrogen atom is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 may contain 1 or 2 heteroatoms selected from may also be) substituted by cycloalkyl. Specifically, for example, R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 together with the carbon to which each is bonded, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, epoxy, tetrahydrofuran , Piperidine and the like can be formed.

　一般式（I）中、R4、R5、R6、R7、R8、R9、R10及びR11は、各々が結合する炭素原子とは別の炭素原子上の、任意のR4、R5、R6、R7、R8、R9、 R10又はR11と結合して、任意に置換されてもよい3～8員環を形成することができ、当該3～8員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよい。具体的には、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、エポキシ、テトラヒドロフラン、ピペリジンなどを形成することができる。 In the general formula (I), R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are any R on a carbon atom different from the carbon atom to which each is bonded. 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 can be combined to form an optionally substituted 3- to 8-membered ring. The member ring may be an oxygen atom, a sulfur atom or a nitrogen atom, which may be substituted by C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl. 1 or 2 heteroatoms selected from the above may be included. Specifically, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, epoxy, tetrahydrofuran, piperidine and the like can be formed.

　前述の「任意に置換されてもよい」とは、当該炭素が、C1－C6アルキル、C1－C6アルコキシ、ハロゲン原子、水酸基、オキソ基などによって置換されてもよいことを表し、例えば次のような構造が挙げられる。 The above-mentioned “optionally substituted” means that the carbon may be substituted by C 1 -C 6 alkyl, C 1 -C 6 alkoxy, a halogen atom, a hydroxyl group, an oxo group, etc. Examples include the following structures.

Figure JPOXMLDOC01-appb-C000005
Figure JPOXMLDOC01-appb-C000005

　一般式（I）中、R4、R5、R6、R7、R8、R9、R10及びR11は、それらが結合する炭素原子と隣り合った炭素原子上の任意のR4、R5、R6、R7、R8、R9、 R10又はR11と結合することができ、例えば、二重結合を形成することができる。 In general formula (I), R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are any R 4 on the carbon atom adjacent to the carbon atom to which they are bonded. , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 , for example, a double bond can be formed.

　そして、前記一般式（I）の式中、Aは酸素原子、硫黄原子、SO、SO2又はCR8R9であり；Wは酸素原子又は硫黄原子であり；Zは酸素原子、硫黄原子又はCR10R11であり；mは0、１又は2であり；nは0、１又は2であり；但し、0≦n+m≦3であり；qは0、１又は2であり；R1はハロC1－C6アルキルであり；R2は水素原子又はC1－C12アルコキシカルボニルであり；R3はハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、Yで置換されてもよいフェニル又はシアノであり；R4、R5、R6、R7、R8、R9、R10及びR11は、それぞれ同一又は異なってもよく、水素原子、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C3－C6シクロアルキルC1－C6アルキル、Yで置換されてもよいフェニル、Yで置換されてもよいフェニルC1－C6アルキル、C1－C6アルキルカルボニルオキシ、水酸基又はシアノであり；R4とR5、R6とR7、R8とR9及びR10とR11は各々互いに結合して、任意に置換されてもよい3～7員環を形成することができ、当該3～7員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく、或いは、オレフィン、カルボニル又はチオカルボニルを形成することができ；R4、R5、R6、R7、R8、R9、R10及びR11は、各々が結合する炭素原子とは別の炭素原子上の、任意のR4、R5、R6、R7、R8、R9、 R10又はR11と結合して、任意に置換されてもよい3～8員環を形成することができ、当該3～8員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく；R4、R5、R6、R7、R8、R9、R10及びR11は、それらが結合する炭素原子と隣り合った炭素原子上の任意のR4、R5、R6、R7、R8、R9、R10又はR11と結合することができ；Yは、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルコキシ、ハロC1－C6アルコキシ、C1－C6アルキルチオ、ハロC1－C6アルキルチオ、C1－C6アルキルスルフィニル、ハロC1－C6アルキルスルフィニル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、カルボキシル、C1－C6アルキルカルボニル、ハロC1－C6アルキルカルボニル、C1－C6アルコキシカルボニル、ハロC1－C6アルコキシカルボニル、アミノ、モノ（C1－C6アルキル）アミノ、モノ（ハロC1－C6アルキル）アミノ、ジ（C1－C6アルキル）アミノ、ジ（ハロC1－C6アルキル）アミノ、シアノ、ニトロ又は水酸基である；ことがより好ましい。 In the general formula (I), A is an oxygen atom, sulfur atom, SO, SO 2 or CR 8 R 9 ; W is an oxygen atom or sulfur atom; Z is an oxygen atom, sulfur atom or CR 10 R 11 ; m is 0, 1 or 2; n is 0, 1 or 2; provided that 0 ≦ n + m ≦ 3; q is 0, 1 or 2; R 1 is halo C 1 -C 6 alkyl; R 2 is hydrogen atom or C 1 -C 12 alkoxycarbonyl; R 3 is halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted optionally C 3 -C be 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, phenyl or cyano optionally substituted with Y; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 may be the same or different and may be substituted with a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 1 -C 6 alkyl. Good C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, phenyl optionally substituted with Y, phenyl optionally substituted with Y C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, hydroxyl or cyano; R 4 and R 5 , R 6 and R 7 , R 8 and R 9 and R 10 and R 11 can be bonded to each other to form an optionally substituted 3- to 7-membered ring. Is an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is a C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cyclo 1 or 2 heteroatoms selected from (which may be substituted by alkyl) or may form an olefin, carbonyl or thiocarbonyl; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , on a carbon atom different from the carbon atom to which each is bonded. It can combine with R 10 or R 11 to form an optionally substituted 3- to 8-membered ring, and the 3- to 8-membered ring is an oxygen atom, a sulfur atom or a nitrogen atom (the nitrogen atom is 1 or 2 heteroatoms selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl) Well; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R on the carbon atom adjacent to the carbon atom to which they are attached. 6 , R 7 , R 8 , R 9 , R 10 or R 11 ; Y is a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl optionally substituted with C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 Cycloalkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, carboxyl, C 1 -C 6 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo C 1 -C 6 alkoxycarbonyl, amino, mono (C 1 -C 6 alkyl) amino, mono (halo C 1 -C 6 A Kill) amino, di (C 1 -C 6 alkyl) amino, di (halo C 1 -C 6 alkyl) amino, cyano, and nitro or hydroxyl; it is more preferred.

　或いは、一般式（I）中のAとしては、－Ｏ－、－Ｓ－、－ＳＯ－、－ＳＯ２－、－ＣＨ２－、－ＣＨＭｅ－、－ＣＨＥｔ－、－ＣＭｅ２－、－ＣＨＰｈ－、－ＣＨＣＦ３－、－Ｃ（＝Ｏ）－がより好ましい（但し、Ｍｅはメチル基、Ｅｔはエチル基、Ｐｈはフェニル基を示す）。 Alternatively, A in the general formula (I) includes —O—, —S—, —SO—, —SO 2 —, —CH 2 —, —CHMe—, —CHEt—, —CMe 2 —, —CHPh. —, —CHCF 3 —, and —C (═O) — are more preferable (where Me represents a methyl group, Et represents an ethyl group, and Ph represents a phenyl group).

　一般式（I）中のZとしては、－Ｏ－、－Ｓ－、－ＣＨ２－、－ＣＨＭｅ－、－ＣＨＥｔ－、－ＣＭｅ２－、－ＣＨn-Ｐｒ－、－ＣＨ（ＣＨ２ＣＨＣＨ２）－、－ＣＨＰｈ－、－ＣＨＣＦ３－、－ＣＨＣＯ２Ｈ－、－ＣＨＣＯ２Ｍｅ－、－ＣＨＣＯ２Ｅｔ－、－ＣＨ（ＣＨ２Ｃ≡ＣＨ）－がより好ましい（但し、n-Ｐｒはｎ－プロピル基を示す）。 As Z in the general formula (I), -O -, - S -, - CH 2 -, - CHMe -, - CHEt -, - CMe 2 -, - CHn-Pr -, - CH (CH 2 CHCH 2 ) —, —CHPh—, —CHCF 3 —, —CHCO 2 H—, —CHCO 2 Me—, —CHCO 2 Et—, —CH (CH 2 C≡CH) — are more preferred (where n-Pr is represents an n-propyl group).

　一般式（I）中のR1としては、－ＣＨＦ２、－ＣＦ３、－ＣＣｌ３、－ＣＨ２ＣＦ３がより好ましい。 R 1 in the general formula (I) is more preferably —CHF 2 , —CF 3 , —CCl 3 , —CH 2 CF 3 .

　一般式（I）中のR2としては、－Ｈ、－Ｍｅ、－Ｅｔ、－n-Ｐｒ、－i-Ｐｒ、－c-Ｐｒ、－n-Ｂｕ、－ＣＯＭｅ、－ＣＯＥｔ、－ＣＯn-Ｐｒ、－ＣＯi-Ｐｒ、－ＣＯc-Ｐｒ、－ＣＯn-Ｂｕ、－ＣＯi-Ｂｕ、－ＣＯs-Ｂｕ、－ＣＯt-Ｂｕ、－ＣＯc-Ｂｕ、－ＣＯＣＨ２t-Ｂｕ、－ＣＯＰｈ、－ＣＯn-Ｃ５Ｈ１１、－ＣＯn-Ｃ６Ｈ１３、－ＣＯn-Ｃ７Ｈ１５、－ＣＯn-Ｃ８Ｈ１７、－ＣＯn-Ｃ９Ｈ１９、－ＣＯn-Ｃ１０Ｈ２１、－ＣＯn-Ｃ１１Ｈ２３、－ＣＯn-Ｃ１２Ｈ２５、－ＣＯ２Ｍｅ、－ＣＯ２Ｅｔ、－ＣＯ２n-Ｐｒ、－ＣＯ２i-Ｐｒ、－ＣＯ２n-Ｂｕ、－ＣＯ２i-Ｂｕ、－ＣＯ２s-Ｂｕ、－ＣＯ２t-Ｂｕ、－ＣＯ２ＣＨ２t-Ｂｕ、－ＣＯ２n-Ｃ５Ｈ１１、－ＣＯ２n-Ｃ６Ｈ１３、－ＣＯ２n-Ｃ７Ｈ１５、－ＣＯ２n-Ｃ８Ｈ１７、－ＣＯ２n-Ｃ９Ｈ１９、－ＣＯ２n-Ｃ１０Ｈ２１、－ＣＯ２n-Ｃ１１Ｈ２３、－ＣＯ２n-Ｃ１２Ｈ２５、－ＣＯ２Ｐｈ、－ＣＯ２ＣＨ２Ｐｈ、－ＣＨ２（２，４－（ＭｅＯ）２－Ｐｈ）、－ＣＨ２（３，５－（ＭｅＯ）２－Ｐｈ）、－ＣＨ２Ｐｈ、－ＣＨ２（４－ＭｅＯ－Ｐｈ）、－ＣＨ２ＯＭｅ、－ＣＨ２ＯＥｔ、－ＣＨ２ＯＣＨ２ＣＦ３、－ＣＨ２ＳＭｅ、－ＣＨ２ＳＯＭｅ、－ＣＨ２ＳＯ２Ｍｅ、－ＣＨ２ＳＣＨ２Ｐｈ、－ＣＨ２ＳＯＣＨ２Ｐｈ、－ＣＨ２ＳＯ２ＣＨ２Ｐｈ、－ＣＨ２ＣＨ＝ＣＨ２、－ＣＨ２ＣＮ、－ＣＨ２ＣＯＭｅ、－ＣＨ２ＣＯＥｔ、－ＣＨ２ＣＯt-Ｂｕ、－ＣＨ２ＣＯＰｈ、－ＣＨ２ＣＯ２Ｍｅ、－ＣＨ２ＣＯ２Ｅｔ、－ＣＨ２ＯＣＯＭｅ、－ＣＨ２ＯＣＯＥｔ、－ＣＨ２ＯＣＯn-Ｐｒ、－ＣＨ２ＯＣＯi-Ｐｒ、－ＣＨ２ＯＣＯc-Ｐｒ、－ＣＨ２ＯＣＯn-Ｂｕ、－ＣＨ２ＯＣＯi-Ｂｕ、－ＣＨ２ＯＣＯt-Ｂｕ、－ＣＨ２ＯＣＯc-Ｂｕ、－ＣＨ２ＯＣＯＰｈ、－ＣＨ（ＣＨ３）ＯＣＯＭｅ、－ＣＨ（ＣＨ３）ＯＣＯＥｔ、－ＣＨ（ＣＨ３）ＯＣＯn-Ｐｒ、－ＣＨ（ＣＨ３）ＯＣＯi-Ｐｒ、－ＣＨ（ＣＨ３）ＯＣＯt-Ｂｕ、－ＣＨ２ＯＣＯ２Ｍｅ、－ＣＨ２ＯＣＯ２Ｅｔ、－ＣＨ２ＯＣＯ２n-Ｐｒ、－ＣＨ２ＯＣＯ２i-Ｐｒ、－ＣＨ２ＯＣＯ２c-Ｐｒ、－ＣＨ２ＯＣＯ２n-Ｂｕ、－ＣＨ２ＯＣＯ２i-Ｂｕ、－ＣＨ２ＯＣＯ２t-Ｂｕ、－ＣＨ２ＯＣＯ２c-Ｂｕ、－ＣＨ２ＯＣＯ２c-Ｈｅｘ、－ＣＨ2ＯＣＯ２ＣＨ２t-Ｂｕ、－ＣＨ２ＯＣＯ２Ｃ（ＣＨ３）２ＣＨ２ＣＨ３－、－ＣＨ（ＣＨ３）ＯＣＯ２Ｍｅ、－ＣＨ（ＣＨ３）ＯＣＯ２Ｅｔ、－ＣＨ（ＣＨ３）ＯＣＯ２n-Ｐｒ、－ＣＨ（ＣＨ３）ＯＣＯ２i-Ｐｒ、－ＣＨ（ＣＨ３）ＯＣＯ２c-Ｐｒ、－ＣＨ（ＣＨ３）ＯＣＯ２n-Ｂｕ、－ＣＨ（ＣＨ３）ＯＣＯ２i-Ｂｕ、－ＣＨ（ＣＨ３）ＯＣＯ２t-Ｂｕ、－ＣＨ（ＣＨ３）ＯＣＯ２c-Ｈｅｘ、－ＣＨ２ＯＣＯ２Ｐｈ、－ＣＨ２ＯＣＯ２（２－Ｆ-Ｐｈ）、－ＣＨ２ＯＣＯ２（３－Ｆ-Ｐｈ）、－ＣＨ２ＯＣＯ２（４－Ｆ-Ｐｈ）、－ＣＨ２ＯＣＯ２（２－Ｍｅ-Ｐｈ）、－ＣＨ２ＯＣＯ２（３－Ｍｅ-Ｐｈ）、－ＣＨ２ＯＣＯ２（４－Ｍｅ-Ｐｈ）、－ＣＨ２ＯＣＯＮＭｅ２、－ＣＨ２ＯＣＯＮＭｅＰｈ、－ＣＮ、－ＣＨ２ＳＣＮ、－ＣＯ（２－ＮＯ２－Ｐｈ）、－ＣＯ（３－ＮＯ２－Ｐｈ）、－ＣＯ（４－ＮＯ２－Ｐｈ）、－ＣＯＣＦ３、－ＣＯＣＨ２Ｃｌ、－ＣＯＣＨ２ＣＨ２Ｃｌ、－ＣＯＣＨ２ＣＨ２ＣＨ２Ｃｌ、－ＣＯＣＨ２ＯＭｅ、－ＣＯＣＨ２ＯＥｔ、－ＣＯＣＨ２ＣＨ２ＣＯ２Ｍｅ、－ＣＯ２ＣＨ（ＣＨ３）Ｃｌ、－ＣＯ２ＣＨ（i-Ｃ３Ｈ７）Ｃｌ、－ＣＯ２Ｃ（ＣＨ３）２ＣＣｌ３、－ＣＯ２ＣＨ２Ｃｌ、－ＣＯ２ＣＨ２ＯＭｅ、－ＣＯ２ＣＨ２ＯＣＨ２ＣＨ２ＯＭｅ、－Ｃ（Ｏ）ＳＭｅ、－Ｃ（Ｏ）ＳＥｔ、－Ｃ（Ｏ）Ｓn-Ｐｒ、－Ｃ（Ｏ）Ｓi-Ｐｒ、－Ｃ（Ｏ）Ｓc-Ｐｒ、－Ｃ（Ｏ）Ｓn-Ｂｕ、－Ｃ（Ｏ）Ｓi-Ｂｕ、－Ｃ（Ｏ）Ｓc-Ｂｕ、－ＳＯ２Ｍｅ、－ＳＯ２Ｅｔ、－ＳＯ２n-Ｐｒ、－ＳＯ２i-Ｐｒ、－ＳＯ２c-Ｐｒ、－ＳＯ２n-Ｂｕ、－ＳＯ２i-Ｂｕ、－ＳＯ２s-Ｂｕ、－ＳＯ２c-Ｂｕ、－ＳＯ２n-Ｃ５Ｈ１１、－ＳＯ２n-Ｃ６Ｈ１３、－ＳＯ２Ｐｈ、－ＳＯ２（２－Ｍｅ－Ｐｈ）、－ＳＯ２（３－Ｍｅ－Ｐｈ）、－ＳＯ２（４－Ｍｅ－Ｐｈ）、－ＳＯ２（２－Ｆ－Ｐｈ）、－ＳＯ２（３－Ｆ－Ｐｈ）、－ＳＯ２（４－Ｆ－Ｐｈ）、－ＳＯ２（２－Ｃｌ－Ｐｈ）、－ＳＯ２（３－Ｃｌ－Ｐｈ）、－ＳＯ２（４－Ｃｌ－Ｐｈ）、－ＳＯ２（２－ＮＯ２－Ｐｈ）、－ＳＯ２（３－ＮＯ２－Ｐｈ）、－ＳＯ２（４－ＮＯ２－Ｐｈ）、－ＳＯ２ＣＨ２Ｐｈ、－ＳＯ２ＣＦ３、－ＳＯ２ＣＨ２ＣＦ３、－ＳＯ２ＣＨ２Ｃｌ、－ＳＯ２ＣＨ２ＣＨ２Ｃｌ、－ＳＯ２ＣＨ２ＣＨ２ＣＨ２Ｃｌ、－ＣＯ２Ｃ（ＣＨ３）２ＣＣｌ３、 R 2 in the general formula (I) includes —H, —Me, —Et, —n—Pr, —i—Pr, —c—Pr, —n—Bu, —COMe, —COEt, —COn—. Pr, —COi—Pr, —COc—Pr, —COn—Bu, —COi—Bu, —COs—Bu, —COt—Bu, —COc—Bu, —COCH 2 t-Bu, —COPh, —COn— C 5 H 11, -COn-C 6 H 13, -COn-C 7 H 15, -COn-C 8 H 17, -COn-C 9 H 19, -COn-C 10 H 21, -COn-C 11 H 23 , —CO n —C 12 H 25 , —CO 2 Me, —CO 2 Et, —CO 2 n-Pr, —CO 2 i-Pr, —CO 2 n-Bu, —CO 2 i-Bu, — CO 2 s-Bu, —CO 2 t-Bu, —CO 2 CH 2 t-Bu, —CO 2 n—C 5 H 11 , —CO 2 n—C 6 H 13 , —CO 2 n—C 7 H 15, -C 2 n-C 8 H 17, -CO 2 n-C 9 H 19, -CO 2 n-C 10 H 21, -CO 2 n-C 11 H 23, -CO 2 n-C 12 H 25, -CO 2 Ph, -CO 2 CH 2 Ph , -CH 2 (2,4- (MeO) 2 -Ph), - CH 2 (3,5- (MeO) 2 -Ph), - CH 2 Ph, -CH 2 (4-MeO-Ph), —CH 2 OMe, —CH 2 OEt, —CH 2 OCH 2 CF 3 , —CH 2 SMe, —CH 2 SOMe, —CH 2 SO 2 Me, —CH 2 SCH 2 Ph, -CH 2 SOCH 2 Ph, -CH 2 SO 2 CH 2 Ph, -CH 2 CH = CH 2, -CH 2 CN, -CH 2 COMe, -CH 2 COEt, -CH 2 COt-Bu, -CH 2 COPh , -CH 2 CO 2 Me, -CH 2 CO 2 Et, CH 2 OCOMe, -CH 2 OCOEt, -CH 2 OCOn-Pr, -CH 2 OCOi-Pr, -CH 2 OCOc-Pr, -CH 2 OCOn-Bu, -CH 2 OCOi-Bu, -CH 2 OCOt-Bu , —CH 2 OCOc—Bu, —CH 2 OCOPh, —CH (CH 3 ) OCOMe, —CH (CH 3 ) OCOEt, —CH (CH 3 ) OCOn—Pr, —CH (CH 3 ) OCOi—Pr, — CH (CH 3 ) OCOt—Bu, —CH 2 OCO 2 Me, —CH 2 OCO 2 Et, —CH 2 OCO 2 n-Pr, —CH 2 OCO 2 i-Pr, —CH 2 OCO 2 c-Pr, -CH 2 OCO 2 n-Bu, -CH 2 OCO 2 i-Bu, -CH 2 OCO 2 t-Bu, -CH 2 OCO 2 c-Bu, -CH 2 OCO 2 c-Hex, -CH 2 OCO 2 CH 2 t-Bu, - H 2 OCO 2 C (CH 3 ) 2 CH 2 CH 3 -, - CH (CH 3) OCO 2 Me, -CH (CH 3) OCO 2 Et, -CH (CH 3) OCO 2 n-Pr, -CH (CH 3 ) OCO 2 i-Pr, —CH (CH 3 ) OCO 2 c—Pr, —CH (CH 3 ) OCO 2 n—Bu, —CH (CH 3 ) OCO 2 i—Bu, —CH (CH 3 ) OCO 2 t-Bu, —CH (CH 3 ) OCO 2 c-Hex, —CH 2 OCO 2 Ph, —CH 2 OCO 2 (2-F-Ph), —CH 2 OCO 2 (3-F— Ph), —CH 2 OCO 2 (4-F-Ph), —CH 2 OCO 2 (2-Me-Ph), —CH 2 OCO 2 (3-Me-Ph), —CH 2 OCO 2 (4- Me-Ph), - CH 2 OCONMe 2, -CH 2 OCONMePh, -CN, -CH 2 SCN, -CO (2-NO 2 -Ph), - CO (3-NO 2 -Ph), - CO (4-NO 2 -Ph), - COCF 3, -COCH 2 Cl, -COCH 2 CH 2 Cl, —COCH 2 CH 2 CH 2 Cl, —COCH 2 OMe, —COCH 2 OEt, —COCH 2 CH 2 CO 2 Me, —CO 2 CH (CH 3 ) Cl, —CO 2 CH (i-C 3 H 7 ) Cl, —CO 2 C (CH 3 ) 2 CCl 3 , —CO 2 CH 2 Cl, —CO 2 CH 2 OMe, —CO 2 CH 2 OCH 2 CH 2 OMe, —C (O) SMe, —C (O) SEt, —C (O) Sn—Pr, —C (O) Si—Pr, —C (O) Sc—Pr, —C (O) Sn—Bu, —C (O) Si—Bu, —C (O) Sc—Bu, —SO 2 Me, —SO 2 Et, —SO 2 n-Pr, —S O 2 i-Pr, —SO 2 c-Pr, —SO 2 n-Bu, —SO 2 i-Bu, —SO 2 s-Bu, —SO 2 c-Bu, —SO 2 n—C 5 H 11 , -SO 2 n-C 6 H 13 , -SO 2 Ph, -SO 2 (2-Me-Ph), -SO 2 (3-Me-Ph), -SO 2 (4-Me-Ph),- SO 2 (2-F-Ph), —SO 2 (3-F-Ph), —SO 2 (4-F-Ph), —SO 2 (2-Cl—Ph), —SO 2 (3-Cl —Ph), —SO 2 (4-Cl—Ph), —SO 2 (2-NO 2 —Ph), —SO 2 (3-NO 2 —Ph), —SO 2 (4-NO 2 —Ph) , —SO 2 CH 2 Ph, —SO 2 CF 3 , —SO 2 CH 2 CF 3 , —SO 2 CH 2 Cl, —SO 2 CH 2 CH 2 Cl, —SO 2 CH 2 CH 2 CH 2 Cl, —CO 2 C (CH 3 ) 2 CCl 3 ,

Figure JPOXMLDOC01-appb-C000006
Figure JPOXMLDOC01-appb-C000006

Figure JPOXMLDOC01-appb-C000007
Figure JPOXMLDOC01-appb-C000007

がより好ましい（但し、i-Ｐｒはｉ－プロピル基、c-Ｐｒはシクロプロピル基、n-Ｂｕはｎ－ブチル基、i-Ｂｕはｉ－ブチル基、s-Ｂｕはsec－ブチル基、t-Ｂｕはtert－ブチル基、c-Ｂｕはシクロブチル基、n-Ｃ５Ｈ１１はｎ－ペンチル基、n-Ｃ６Ｈ１３はｎ－ヘキシル基、n-Ｃ７Ｈ１５はｎ－ヘプチル基、n-Ｃ８Ｈ１７はｎ－オクチル基、n-Ｃ９Ｈ１９はｎ－ノニル基、n-Ｃ１０Ｈ２１はｎ－デシル基、n-Ｃ１１Ｈ２３はｎ－ウンデシル基、n-Ｃ１２Ｈ２５はｎ－ドデシル基、c-Ｈｅｘはシクロヘキシル基を示す）。 (Where i-Pr is an i-propyl group, c-Pr is a cyclopropyl group, n-Bu is an n-butyl group, i-Bu is an i-butyl group, s-Bu is a sec-butyl group, t-Bu is tert-butyl group, c-Bu is cyclobutyl group, n-C 5 H 11 is n-pentyl group, n-C 6 H 13 is n-hexyl group, n-C 7 H 15 is n-heptyl group N-C 8 H 17 is an n-octyl group, n-C 9 H 19 is an n-nonyl group, n-C 10 H 21 is an n-decyl group, n-C 11 H 23 is an n-undecyl group, n-C 12 H 25 represents an n-dodecyl group, and c-Hex represents a cyclohexyl group).

　一般式（I）中のR4、R5としては、－Ｈ、－Ｍｅ、－Ｅｔ、－Ｐｈ、＝Ｏ、－ＣＯ２Ｈ、－ＣＯ２Ｍｅ、－ＣＯ２Ｅｔ、－ＣＯ２n-Ｂｕ、－ＣＮがより好ましい。 R 4 and R 5 in the general formula (I) include —H, —Me, —Et, —Ph, ═O, —CO 2 H, —CO 2 Me, —CO 2 Et, —CO 2 n— Bu and -CN are more preferable.

　一般式（I）中のR6、R7としては、－Ｈ、－ＯＨ、－Ｃｌ、－Ｍｅ、－Ｅｔ、－n-Ｐｒ、－i-Ｐｒ、－ｃ-Ｐｒ、－Ｐｈ、－（ＣＨ２）４－、－（ＣＨ２）５－、－（ＣＨ２）６－、－（ＣＨ２）２－Ｏ－（ＣＨ２）２－、－ＯＣＯＣＨ３、－ＣＦ３、－ＣＨ２Ｃｌがより好ましい。 In general formula (I), R 6 and R 7 are —H, —OH, —Cl, —Me, —Et, —n—Pr, —i—Pr, —c—Pr, —Ph, — ( CH 2 ) 4 —, — (CH 2 ) 5 —, — (CH 2 ) 6 —, — (CH 2 ) 2 —O— (CH 2 ) 2 —, —OCOCH 3 , —CF 3 , —CH 2 Cl Is more preferable.

　従って、ヘテロアリールスルホンアミド系化合物の好適な具体例としては、一般式（I）中のA、Z、R1～R7の上記好ましい置換基を適宜組み合わせてなる化合物が挙げられ、さらに好適な具体例としては、実施例に記載の各種化合物が挙げられ、特に好適な具体例としては、実施例に記載の各種化合物の中で、物性を測定している化合物が挙げられる。 Accordingly, preferred specific examples of the heteroarylsulfonamide-based compound include compounds obtained by appropriately combining the above preferred substituents of A, Z and R 1 to R 7 in the general formula (I). Specific examples include various compounds described in Examples, and particularly preferable specific examples include compounds measuring physical properties among various compounds described in Examples.

　一般式（I）のヘテロアリールスルホンアミド系化合物の塩としては、農業上許容されるものであればあらゆる塩が含まれるが、例えば、ナトリウム塩、カリウム塩のようなアルカリ金属塩；マグネシウム塩、カルシウム塩のようなアルカリ土類金属塩；ジメチルアミン塩、トリエチルアミン塩のようなアミン塩；塩酸塩、過塩素酸塩、硫酸塩、硝酸塩のような無機酸塩；酢酸塩、メタンスルホン酸塩のような有機酸塩などが挙げられる。 The salt of the heteroarylsulfonamide compound of the general formula (I) includes any salt that is agriculturally acceptable. For example, an alkali metal salt such as a sodium salt or a potassium salt; a magnesium salt, Alkaline earth metal salts such as calcium salts; amine salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; acetates and methanesulfonates Such organic acid salts.

　一般式（I）のヘテロアリールスルホンアミド系化合物には、光学異性体のような異性体が存在する場合があるが、本発明には各異性体及び異性体混合物の双方が含まれる。本願明細書においては、特に言及しない限り、異性体は混合物として記載する。尚、本発明には、当該技術分野における技術常識の範囲内において、前記異性体以外の各種異性体も含まれる。また、異性体の種類によっては、前記一般式（I）とは異なる化学構造となる場合があるが、当業者であればそれらが異性体の関係にあることが十分認識できる為、本発明の範囲内であることは明らかである。 In the heteroarylsulfonamide compound of the general formula (I), there may be an isomer such as an optical isomer, but the present invention includes both isomers and isomer mixtures. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention includes various isomers other than the isomers within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from that of the general formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.

　前記一般式（I）のヘテロアリールスルホンアミド系化合物又はその塩（以下、本発明に係る化合物と略す）は、以下の製造方法、並びに通常の塩の製造方法に従って製造することができるが、これらの方法に限定されるものではない。 The heteroarylsulfonamide-based compound of the general formula (I) or a salt thereof (hereinafter abbreviated as the compound according to the present invention) can be produced according to the following production methods and ordinary salt production methods. It is not limited to the method.

　・製造方法〔１〕 Manufacturing method [1]

Figure JPOXMLDOC01-appb-C000008
Figure JPOXMLDOC01-appb-C000008

（式中、A、W、Z、m、n、ｑ、Ｒ１、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びＲ７は前述の通りであり、Ｒ２-aはC1－C12アルコキシカルボニル、C1－C12アルキルカルボニル、ハロC1－C6アルキルカルボニル、シクロC3-C6アルキルカルボニル、シクロC3-C6アルキルC1-C6アルキルカルボニル、C2-C6アルケニルカルボニル、Yで置換されてもよいフェニルC2-C6アルケニルカルボニル、Yで置換されてもよいフェニルカルボニル、Yで置換されてもよい複素環カルボニル、ハロC1－C12アルコキシカルボニル、C1-C6アルキルで置換されてもよいシクロC3-C6アルコキシカルボニル、C2-C6アルケニルオキシカルボニル、ハロC2-C6アルケニルオキシカルボニル、C2-C6アルキニルオキシカルボニル、C1-C6アルコキシC1-C6アルコキシカルボニル、C1-C6アルキルチオC1-C6アルコキシカルボニル、C1-C6アルキルスルフィニルC1-C6アルコキシカルボニル、C1-C6アルキルスルホニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルハロC1-C6アルコキシカルボニル、Yで置換されてもよいフェノキシカルボニル、Yで置換されてもよいフェノキシC1-C6アルキルカルボニル、C1-C6アルキルチオカルボニル、ハロC1-C6アルキルチオカルボニル、モノC1-C6アルキルアミノカルボニル、モノ（ハロC1-C6アルキル）アミノカルボニル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニル、ジ（ハロC1-C6アルキル）アミノカルボニル、C1-C6アルコキシC1-C6アルキルカルボニル、C1-C6アルコキシカルボニルC1-C6アルキルカルボニル、C1-C6アルコキシオキサリル、C1-C6アルキルスルホニル、ハロC1-C6アルキルスルホニル、Yで置換されてもよいフェニルスルホニル、アミノスルホニル、モノC1-C6アルキルアミノスルホニル、ジC1-C6アルキルアミノスルホニル、Yで置換されてもよい複素環スルホニル、シクロC3-C6アルキルスルホニル、C1-C6アルキル、ハロC1-C6アルキル、C2-C6アルケニル、ハロC2-C6アルケニル、C2-C6アルキニル、ハロC2-C6アルキニル、Yで置換されてもよいフェニルC1-C6アルキル、Yで置換されてもよいフェニルカルボニルC1-C6アルキル、C1-C6アルコキシC1-C6アルキル、ハロC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシC1-C6アルコキシC1-C6アルキル、トリC1-C6アルキルシリルC1-C6アルコキシC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルC1-C6アルキル、C1-C6アルキルカルボニルオキシC1-C6アルキル、シクロC3-C6アルキルカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルキル、Yで置換されてもよい複素環カルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルオキシC1-C6アルキル、シクロC3-C6アルコキシカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェノキシカルボニルオキシC1-C6アルキル、モノC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいN-C1-C6アルキル-N-フェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルチオC1-C6アルキル、Yで置換されてもよいフェニルスルフィニルC1-C6アルキル、Yで置換されてもよいフェニルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルチオC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルホニルC1-C6アルキル、C1-C6アルキルチオC1-C6アルキル、ハロC1-C6アルキルチオC1-C6アルキル、C1-C6アルキルスルフィニルC1-C6アルキル、C1-C6アルキルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルフィニルC1-C6アルキル、チオシアナトC1-C6アルキル、シアノC1-C6アルキル、Yで置換されてもよい複素環C1-C6アルキル、C1-C6アルキルカルボニルC1-C6アルキル又はシアノである。Lはハロゲン原子等の脱離基を示す。）
　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；アセトニトリル、N,N-ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、1,4-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類；メタノール、エタノール、イソプロパノールのようなアルコール類；水などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 (In the formula, A, W, Z, m, n, q, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are as described above, and R 2 -a is C 1 -C 12. Alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo C 3 -C 6 alkylcarbonyl, cyclo C 3 -C 6 alkyl C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenyl Carbonyl, phenyl C 2 -C 6 alkenylcarbonyl optionally substituted with Y, phenylcarbonyl optionally substituted with Y, heterocyclic carbonyl optionally substituted with Y, halo C 1 -C 12 alkoxycarbonyl, C 1 -C 6 alkyl optionally substituted cyclo C 3 -C be 6 alkoxycarbonyl, C 2 -C 6 alkenyloxycarbonyl, halo C 2 -C 6 alkenyloxycarbonyl, C 2 -C 6 alkynyloxy-carbonyl, C 1 - C 6 alkoxy C 1 -C 6 alkoxycarbonyl, C 1 -C 6 Alkylthio C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkoxycarbonyl, phenyl optionally substituted with Y C 1 - C 6 alkoxycarbonyl, Y which may be substituted Feniruharo C 1 -C 6 alkoxycarbonyl, good phenoxycarbonyl which may be substituted with Y, which may be substituted by Y phenoxy C 1 -C 6 alkylcarbonyl, C 1 - C 6 alkylthiocarbonyl, halo C 1 -C 6 alkylthiocarbonyl, mono C 1 -C 6 alkylaminocarbonyl, mono (halo C 1 -C 6 alkyl) aminocarbonyl, two C 1 -C 6 alkyl on the nitrogen atom Di C 1 -C 6 alkylaminocarbonyl, di (halo C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl which may be bonded to each other to form a 3- to 8-membered ring Carbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxyoxalyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, phenyl optionally substituted by Y Sulfonyl, aminosulfonyl, mono C 1 -C 6 alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, heterocyclic sulfonyl optionally substituted with Y, cyclo C 3 -C 6 alkylsulfonyl, C 1 -C 6 Alkyl, halo C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halo C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo C 2 -C 6 alkynyl, phenyl C 1 optionally substituted with Y -C 6 alkyl, phenylcarbonyl C 1 -C 6 alkyl optionally substituted with Y, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halo C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl, tri C 1 -C 6 Alkylsilyl C 1 -C 6 alkoxy C 1 -C 6 alkyl, phenyl optionally substituted by Y C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, optionally substituted with phenylcarbonyloxy C 1 -C 6 alkyl, Y substituted Heterocyclic carbonyloxy C 1 -C 6 alkyl, optionally substituted with phenylcarbonyloxy C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl, optionally substituted with Y phenoxycarbonyloxy C 1 -C 6 alkyl, mono-C 1 -C 6 alkylaminocarbonyloxy C 1 -C 6 alkyl, two C 1 -C 6 alkyl on the nitrogen atom Le di may form a 3- to 8-membered ring bonded to each other C 1 -C 6 alkylaminocarbonyloxy C 1 -C 6 alkyl, phenyl aminocarbonyl optionally substituted by a Y-oxy C 1 -C 6 NC, optionally substituted with Y 1 NC 1 -C 6 alkyl-N-phenylaminocarbonyloxy C 1 -C 6 alkyl, optionally substituted with Y phenylthio C 1 -C 6 alkyl, optionally substituted with Y good phenylsulfinyl C 1 -C 6 alkyl, phenyl sulfonyl optionally substituted by Y C 1 -C 6 alkyl, phenyl which may be substituted by Y C 1 -C 6 alkylthio C 1 -C 6 alkyl, substituted with Y Phenyl C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halo C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl, Y In optionally substituted phenyl C 1 -C be 6 alkylsulfinyl C 1 -C 6 alkyl, thiocyanato C 1 -C 6 alkyl, cyano C 1 -C 6 alkyl, heterocyclic C 1 -C be substituted by Y 6 alkyl, C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl or cyano. L represents a leaving group such as a halogen atom. )
The above reaction can be performed in the presence of a solvent, if necessary. The solvent may be any solvent that is inert to the reaction, such as halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, Aromatic hydrocarbons such as chlorobenzene; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethyl Aprotic polar solvents such as phosphoric acid triamide (HMPA), sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane; methanol Like ethanol, isopropanol Alcohols; and water. As the solvent, one or more of these can be appropriately selected.

　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、有機塩基でも無機塩基でもいずれでもよい。有機塩基としては、例えば、トリエチルアミン、ジイソプロピルエチルアミンのような第三級アミン類；1,8-ジアザビシクロ[5.4.0]-7-ウンデセン（DBU）；ピリジン；4-(ジメチルアミノ)ピリジン；2,6-ルチジンなどが挙げられる。無機塩基としては、例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのようなアルカリ金属炭酸塩；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩；炭酸カルシウム、炭酸バリウムのようなアルカリ土類金属炭酸塩；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物；水酸化カルシウム、水酸化バリウムのようなアルカリ土類金属水酸化物；ナトリウムメトキシド、ナトリウムエトキシド、カリウムターシャリーブトキシドなどのアルカリ金属アルコキシド類；ナトリウムヒドリド、カリウムヒドリドなどのアルカリ金属ヒドリド類；ブチルリチウムなどのアルカリ金属アルキル類；酢酸ナトリウム、酢酸カリウムなどのアルカリ金属カルボン酸塩などが挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 The above reaction can be performed in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); pyridine; 4- (dimethylamino) pyridine; Examples include 6-lutidine. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium methoxide, sodium ethoxide, Examples include alkali metal alkoxides such as potassium tertiary butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; alkali metal alkyls such as butyl lithium; alkali metal carboxylates such as sodium acetate and potassium acetate. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応は、必要に応じて相間移動触媒の存在下に行うことができる。相間移動触媒としては、例えば、テトラノルマルブチルアンモニウムブロミド、ベンジルトリエチルアンモニウムブロミドのような四級アンモニウム塩；18-クラウン6-エーテル；などが挙げられる。また、上記反応はトリメチルアミン塩酸塩などの添加物存在下に行うことができる。 The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown 6-ether; The above reaction can be performed in the presence of an additive such as trimethylamine hydrochloride.

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、望ましくは０℃から使用する溶媒の沸点の範囲内、反応時間は、通常１分～４８時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within the range of 0 ° C. to 150 ° C., desirably within the range of the boiling point of the solvent used from 0 ° C., and the reaction time is usually within the range of 1 minute to 48 hours.

　・製造方法〔２〕 Manufacturing method [2]

Figure JPOXMLDOC01-appb-C000009
Figure JPOXMLDOC01-appb-C000009

（式中、A、W、Z、m、n、ｑ、Ｒ１、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びＲ７は前述の通りである。）
　一般式（I‐a）で表される化合物は、後述の方法で合成できる中間体（II）と、市販されている、あるいは既知の方法に準じて合成できる中間体（III）との反応により合成することができる。 (In the formula, A, W, Z, m, n, q, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are as described above.)
The compound represented by the general formula (Ia) is obtained by reacting an intermediate (II) that can be synthesized by the method described below with an intermediate (III) that is commercially available or that can be synthesized according to a known method. Can be synthesized.

　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；ノルマルヘキサン、ノルマルヘプタンのような炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；アセトニトリル、N,N-ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、1,4-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be performed in the presence of a solvent, if necessary. The solvent may be any solvent as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, Aromatic hydrocarbons such as chlorobenzene; hydrocarbons such as normal hexane and normal heptane; esters such as methyl acetate, ethyl acetate and propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide Aprotic polar solvents such as (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1 A, such as 2-dimethoxyethane Such as Le acids and the like. As the solvent, one or more of these can be appropriately selected.

　上記反応は、必要に応じて相間移動触媒の存在下に行うことができる。相間移動触媒としては、製造方法〔１〕に例示した触媒と同様の触媒が挙げられる。 The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include the same catalysts as those exemplified in the production method [1].

　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、有機塩基でも無機塩基でもいずれでもよく、製造方法〔１〕に例示した塩基と同様の塩基が挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 The above reaction can be performed in the presence of a base as necessary. The base may be either an organic base or an inorganic base, and examples thereof include the same bases as exemplified in the production method [1]. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応は、必要に応じて酸触媒の存在下に行うことができる。酸触媒としては、例えば、ギ酸、酢酸、メタンスルホン酸、ｐ－トルエンスルホン酸、トリフルオロ酢酸、トリフルオロメタンスルホン酸のような有機酸；塩酸、硫酸、臭化水素のような無機酸類；塩化亜鉛、四塩化チタン、塩化すず、塩化アルミ、塩化鉄、三フッ化ホウ素－エーテル錯体のようなルイス酸類などが挙げられる。 The above reaction can be carried out in the presence of an acid catalyst as necessary. Examples of the acid catalyst include organic acids such as formic acid, acetic acid, methanesulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid and trifluoromethanesulfonic acid; inorganic acids such as hydrochloric acid, sulfuric acid and hydrogen bromide; zinc chloride Lewis acids such as titanium tetrachloride, tin chloride, aluminum chloride, iron chloride, boron trifluoride-ether complex, and the like.

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、望ましくは室温から還流温度までの範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature of the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the reflux temperature, and the reaction time is usually in the range of 1 minute to 72 hours.

　・製造方法〔３〕 Manufacturing method [3]

Figure JPOXMLDOC01-appb-C000010
Figure JPOXMLDOC01-appb-C000010

（式中、A、W、Z、m、n、ｑ、Ｒ１、Ｒ３、Ｒ４、Ｒ５、Ｒ６及びＲ７は前述の通りである。Ｒ２-bはC1－C12アルコキシカルボニル、C1－C12アルキルカルボニル、ハロC1－C6アルキルカルボニル、シクロ（C3-C6）アルキルカルボニル、シクロ（C3-C6）アルキル（C1－C6）アルキルカルボニル、（C2-C6）アルケニルカルボニル、Yで置換されてもよいフェニル（C2-C6）アルケニルカルボニル、Yで置換されてもよいフェニルカルボニル、Yで置換されてもよい複素環カルボニル、ハロ（C1－C12）アルコキシカルボニル、（C1－C6）アルキルで置換されてもよいシクロ（C3-C6）アルコキシカルボニル、（C2-C6）アルケニルオキシカルボニル、ハロ（C2-C6）アルケニルオキシカルボニル、（C2-C6）アルキニルオキシカルボニル、（C1-C6）アルコキシ（C1-C6）アルコキシカルボニル、（C1-C6）アルキルチオ（C1-C6）アルコキシカルボニル、（C1-C6）アルキルスルフィニル（C1-C6）アルコキシカルボニル、（C1-C6）アルキルスルホニル（C1-C6）アルコキシカルボニル、Yで置換されてもよいフェニル（C1-C6）アルコキシカルボニル、Yで置換されてもよいフェニルハロ（C1-C6）アルコキシカルボニル、Yで置換されてもよいフェノキシカルボニル、Yで置換されてもよいフェノキシ（C1-C6）アルキルカルボニル、（C1-C6）アルキルチオカルボニル、ハロ（C1-C6）アルキルチオカルボニル、モノ（C1-C6）アルキルアミノカルボニル、モノ（ハロ（C1-C6）アルキル）アミノカルボニル、窒素原子上の２つの（C1-C6）アルキルが互いに結合して３～８員環を形成してもよいジ（C1-C6）アルキルアミノカルボニル、ジ（ハロ（C1-C6）アルキル）アミノカルボニル、（C1-C6）アルコキシ（C1-C6）アルキルカルボニル、（C1-C6）アルコキシカルボニル（C1-C6）アルキルカルボニル、（C1-C6）アルコキシオキサリル、（C1-C6）アルキルスルホニル、ハロ（C1-C6）アルキルスルホニル、Yで置換されてもよいフェニルスルホニル、アミノスルホニル、モノ（C1-C6）アルキルアミノスルホニル、ジ（C1-C6）アルキルアミノスルホニル、Yで置換されてもよい複素環スルホニル、シクロ（C1-C6）アルキルスルホニル又はシアノである。）
　上記反応は、一般の有機合成化学で考えられる方法に準じて行えばよい。塩基を用いることができ、塩基としては、例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのようなアルカリ金属炭酸塩；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩；炭酸カルシウム、炭酸バリウムのようなアルカリ土類金属炭酸塩；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物；水酸化カルシウム、水酸化バリウムのようなアルカリ土類金属水酸化物などが挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 (In the formula, A, W, Z, m, n, q, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are as described above. R 2-b is C 1 -C 12. Alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo (C 3 -C 6 ) alkylcarbonyl, cyclo (C 3 -C 6 ) alkyl (C 1 -C 6 ) alkylcarbonyl, (C 2 -C 6 ) alkenylcarbonyl, phenyl (C 2 -C 6 ) alkenylcarbonyl optionally substituted with Y, phenylcarbonyl optionally substituted with Y, heterocyclic carbonyl optionally substituted with Y, halo (C 1 -C 12 ) alkoxycarbonyl, cyclo (C 3 -C 6 ) alkoxycarbonyl optionally substituted with (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyloxycarbonyl, halo (C 2 -C 6) alkenyloxycarbonyl, (C 2 -C 6) alkynyloxy carbonitrile Le, (C 1 -C 6) alkoxy (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylthio (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) alkylsulfinyl (C 1 -C 6 ) alkoxycarbonyl, (C 1 -C 6 ) alkylsulfonyl (C 1 -C 6 ) alkoxycarbonyl, phenyl optionally substituted with Y (C 1 -C 6 ) alkoxycarbonyl, Y substituted good Feniruharo (C 1 -C 6) alkoxycarbonyl which may be substituted by Y phenoxycarbonyl which may be substituted by Y phenoxy (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) alkyl thiocarbonyl, halo (C 1 -C 6) alkyl thiocarbonyl, mono (C 1 -C 6) alkylaminocarbonyl, mono (halo (C 1 -C 6) alkyl) aminocarbonyl, on the nitrogen atom two (C 1 -C 6 ) Alkyl bonded together May be formed to 8-membered ring di (C 1 -C 6) alkylaminocarbonyl, di (halo (C 1 -C 6) alkyl) aminocarbonyl, (C 1 -C 6) alkoxy (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxycarbonyl (C 1 -C 6) alkylcarbonyl, (C 1 -C 6) alkoxy oxalyl, (C 1 -C 6) alkylsulfonyl, halo (C 1 -C 6 ) alkylsulfonyl, phenylsulfonyl optionally substituted with Y, aminosulfonyl, mono (C 1 -C 6 ) alkylaminosulfonyl, di (C 1 -C 6 ) alkylaminosulfonyl, optionally substituted with Y Ring sulfonyl, cyclo (C 1 -C 6 ) alkylsulfonyl or cyano. )
The above reaction may be performed according to a method considered in general organic synthetic chemistry. A base can be used. Examples of the base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; calcium carbonate and barium carbonate. Alkaline earth metal carbonates such as lithium hydroxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide. It is done. As the base, one or more of these may be appropriately selected and mixed for use.

　また、上記反応は溶媒の存在下で行うことができる。使用する溶媒は、反応に不活性な溶媒であればどのような溶媒でもよく、例えば、メタノール、エタノール、イソプロパノールのようなアルコール類；アセトニトリル、N,N-ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、1,4-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類；水などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be carried out in the presence of a solvent. Any solvent can be used as long as it is inert to the reaction. For example, alcohols such as methanol, ethanol and isopropanol; acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) ), Aprotic polar solvents such as dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2 -Ethers such as dimethoxyethane; water and the like. As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常０℃～１００℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within a range of 0 ° C. to 100 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.

　・製造方法〔４〕 Manufacturing method [4]

Figure JPOXMLDOC01-appb-C000011
Figure JPOXMLDOC01-appb-C000011

（式中、A、Z、m、n、ｑ、Ｒ1、Ｒ3、Ｒ4、Ｒ5、Ｒ6及びＲ7は前述の通りである。）
　上記反応で使用する硫化剤としては、例えば、P4S10やローソン試薬などが挙げられる。また、上記反応は溶媒の存在下で行うことができる。使用する溶媒は、反応に不活性な溶媒であればどのような溶媒でもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；ノルマルヘキサン、ノルマルヘプタンのような炭化水素類；ジエチルエーテル、ターシャリーブチルメチルエーテル、1,4-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 (In the formula, A, Z, m, n, q, R 1 , R 3 , R 4 , R 5 , R 6 and R 7 are as described above.)
Examples of the sulfurizing agent used in the above reaction include P 4 S 10 and Lawesson's reagent. The above reaction can be carried out in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, and carbon tetrachloride; benzene, toluene, xylene, Aromatic hydrocarbons such as nitrobenzene and chlorobenzene; hydrocarbons such as normal hexane and normal heptane; diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane And ethers such as As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within a range of 0 ° C. to 150 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.

　・製造方法〔５〕 ・ Production method [5]

Figure JPOXMLDOC01-appb-C000012
Figure JPOXMLDOC01-appb-C000012

（式中、A、W、Z、m、n、Ｒ１、Ｒ４、Ｒ５、Ｒ６及びＲ７は前述の通りである。Ｒ2-cはC1－C12アルコキシカルボニルであり、Ｒ3-aは臭素、ヨウ素を示す。）
　上記の反応はチエニルハライド（Ｉ‐f）とスズ試薬のパラジウム触媒を用いたスティルカップリング反応により生成したビニルエーテル体（Ｉ－g）を酸処理することによりアルキルカルボニル体（Ｉ－h）を得る反応である。
製造方法〔５〕の各工程について、以下に詳述する。 Wherein A, W, Z, m, n, R 1 , R 4 , R 5 , R 6 and R 7 are as described above. R 2-c is C 1 -C 12 alkoxycarbonyl; R 3-a represents bromine or iodine.)
In the above reaction, an alkylcarbonyl compound (Ih) is obtained by acid treatment of the vinyl ether compound (Ig) produced by the still coupling reaction using thienyl halide (If) and a palladium catalyst of a tin reagent. It is a reaction.
Each process of manufacturing method [5] is explained in full detail below.

　・製造方法〔５－１〕
　　一般式（Ｉ－f）→　一般式（Ｉ－g）
　上記反応で使用するスズ試薬としては、例えば、式中記載のトリブチル(1-エトキシビニル)スズなどである。上記反応で使用するパラジウム触媒としては、一般にスティルカップリング反応で使用されるものであればよく、例えば、Pd2(dba)3、Pd(PPh3)4などが挙げられ、配位子の存在下に行うことができる。配位子としては、例えば、トリフェニルホスフィン、トリターシャリーブチルホスフィン、トリフェニルアルシンのようなものが挙げられる。また、上記反応は、必要に応じて、例えば塩化リチウム、フッ化セシウム、ヨウ化銅などの存在下に行うことができる。 ・ Production method [5-1]
General formula (If) → General formula (Ig)
Examples of the tin reagent used in the above reaction include tributyl (1-ethoxyvinyl) tin described in the formula. The palladium catalyst used in the above reaction is not particularly limited as long as it is generally used in a Still coupling reaction, and examples thereof include Pd 2 (dba) 3 and Pd (PPh 3 ) 4 Can be done below. Examples of the ligand include triphenylphosphine, tritertiary butylphosphine, and triphenylarsine. Moreover, the said reaction can be performed in presence of lithium chloride, a cesium fluoride, copper iodide etc. as needed.

　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；アセトニトリル、N, N-ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ターシャリーブチルメチルエーテル、１,４-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, nitrobenzene and chlorobenzene; acetonitrile, N, N-dimethylformamide (DMF), Aprotic polar solvents such as dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1, And ethers such as 2-dimethoxyethane. As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、望ましくは室温から使用する溶媒の沸点までの範囲内、反応時間は、通常１分～４８時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.

　・製造方法〔５－２〕
　　一般式（Ｉ－g）→　一般式（Ｉ－h）
 上記反応で水と共に使用する酸は、塩酸、硫酸などである。上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、製造方法〔３〕に例示した溶媒と同様の溶媒が挙げられ、これらの1種又は2種以上を適宜選択することができる。 ・ Production method [5-2]
General formula (Ig) → General formula (Ih)
Acids used with water in the above reaction are hydrochloric acid, sulfuric acid and the like. The above reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. Examples thereof include the same solvents as those exemplified in the production method [3], and one or more of these may be selected as appropriate. Can do.

　上記反応の反応温度は、通常０℃～１００℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within a range of 0 ° C. to 100 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.

　本発明で用いる中間体の製造方法を以下に示す。 The method for producing the intermediate used in the present invention is shown below.

　・中間体製造方法〔１〕 Intermediate production method [1]

Figure JPOXMLDOC01-appb-C000013
Figure JPOXMLDOC01-appb-C000013

（式中、ｑ、Ｒ１、Ｒ３及びLは前述の通りである。Ｒ12はC1－C6アルキルを示す。）
　中間体製造方法〔１〕の各工程について、以下に詳述する。 (In the formula, q, R 1 , R 3 and L are as defined above. R 12 represents C 1 -C 6 alkyl.)
Each step of the intermediate production method [1] will be described in detail below.

　・中間体製造方法〔１－１〕
　　一般式（Ｖ）→　一般式（IＶ－a）又は一般式（IＶ－b）
　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、製造方法〔２〕に例示した溶媒と同様の溶媒が挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 Intermediate production method [1-1]
General formula (V) → General formula (IV-a) or General formula (IV-b)
The above reaction can be performed in the presence of a solvent, if necessary. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the production method [2]. As the solvent, one or more of these can be appropriately selected.

　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、有機塩基でも無機塩基でもいずれでもよく、製造方法〔１〕に例示した塩基と同様の塩基が挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 The above reaction can be performed in the presence of a base as necessary. The base may be either an organic base or an inorganic base, and examples thereof include the same bases as exemplified in the production method [1]. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応の反応温度は、通常－７０℃～１５０℃の範囲内、望ましくは、－２０℃～５０℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually in the range of −70 ° C. to 150 ° C., desirably in the range of −20 ° C. to 50 ° C., and the reaction time is usually in the range of 1 minute to 72 hours.

　上記反応は、必要に応じて不活性ガスの下に行うことができる。当該不活性ガスとしては、例えば、アルゴンガス、窒素ガスなどが挙げられる。 The above reaction can be performed under an inert gas as necessary. Examples of the inert gas include argon gas and nitrogen gas.

　・中間体製造方法〔１－２〕
　　一般式（IＶ－b）→　一般式（IＶ－a）
　上記反応は、無溶媒でも進行するが、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、製造方法〔１〕に例示した溶媒と同様の溶媒が挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 Intermediate production method [1-2]
General formula (IV-b) → General formula (IV-a)
The above reaction proceeds even without solvent, but can be carried out in the presence of a solvent, if necessary. The solvent may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the production method [1]. As the solvent, one or more of these can be appropriately selected.

　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、有機塩基でも無機塩基でもいずれでもよい。有機塩基としては、アンモニア、ヒドロキシルアミンなどが挙げられる。無機塩基としては、製造方法〔１〕に例示した塩基と同様の塩基が挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 The above reaction can be performed in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include ammonia and hydroxylamine. As an inorganic base, the base similar to the base illustrated to manufacturing method [1] is mentioned. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応は、必要に応じて相間移動触媒の存在下に行うことができる。相間移動触媒としては、製造方法〔１〕に例示した触媒と同様の触媒が挙げられる。 The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include the same catalysts as those exemplified in the production method [1].

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within a range of 0 ° C. to 150 ° C., and the reaction time is usually within a range of 1 minute to 72 hours.

　・中間体製造方法〔１－３〕
　　一般式（IＶ－a）又は一般式（IＶ－b）→　一般式（IＶ－c）
　上記反応は、一般の有機合成化学で考えられる方法に準じて行えばよい。例えば、塩基を用いることができ、無機塩基としては、製造方法〔１〕に例示した塩基と同様の塩基が挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 Intermediate production method [1-3]
General formula (IV-a) or general formula (IV-b) → General formula (IV-c)
The above reaction may be performed according to a method considered in general organic synthetic chemistry. For example, a base can be used, and examples of the inorganic base include the same bases as exemplified in the production method [1]. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応で、用いる溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、製造方法〔３〕に例示した溶媒と同様の溶媒が挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the production method [3]. As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常－７０℃～１５０℃の範囲内、望ましくは０℃～１００℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within the range of -70 ° C. to 150 ° C., preferably within the range of 0 ° C. to 100 ° C., and the reaction time is usually within the range of 1 minute to 72 hours.

　・中間体製造方法〔１－４〕
　　一般式（IＶ－a）、一般式（IＶ－b）又は一般式（IＶ－c）→　一般式（II）
　上記反応で使用する還元剤としては、例えば、水素化リチウムアルミニウム、水素化ジイソブチルアルミニウム、水素化ビス(2-メトキシエトキシ)アルミニウムナトリウム、水素化ホウ素ナトリウム、水素化ホウ素リチウム、ボランTHF錯体などが挙げられる。 Intermediate production method [1-4]
General formula (IV-a), general formula (IV-b) or general formula (IV-c) → general formula (II)
Examples of the reducing agent used in the above reaction include lithium aluminum hydride, diisobutylaluminum hydride, sodium bis (2-methoxyethoxy) aluminum hydride, sodium borohydride, lithium borohydride, and borane THF complex. It is done.

　上記反応は溶媒の存在下で行うことができる。使用する溶媒としては反応に不活性な溶媒であればどのような溶媒でもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、クロロベンゼンのような芳香族炭化水素類；ジエチルエーテル、ターシャリーブチルメチルエーテル、1,4-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be carried out in the presence of a solvent. The solvent used may be any solvent inert to the reaction, such as halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, Aromatic hydrocarbons such as chlorobenzene; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane, and the like. As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常－７０℃～１５０℃の範囲内、反応時間は、通常１分～７２時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually within a range of -70 ° C to 150 ° C, and the reaction time is usually within a range of 1 minute to 72 hours.

　上記反応は、必要に応じて不活性ガスの下に行うことができる。当該不活性ガスとしては、例えば、アルゴンガス、窒素ガスなどが挙げられる。 The above reaction can be performed under an inert gas as necessary. Examples of the inert gas include argon gas and nitrogen gas.

　・中間体製造方法〔２〕 Intermediate production method [2]

Figure JPOXMLDOC01-appb-C000014
Figure JPOXMLDOC01-appb-C000014

（式中、ｑ、Ｒ１、Ｒ３及びＲ12は前述の通りである。）
　上記反応は、前記中間体製造方法〔１〕に記載の方法に準じて行うことができる。 (In the formula, q, R 1 , R 3 and R 12 are as described above.)
The above reaction can be carried out according to the method described in the above intermediate production method [1].

　・中間体製造方法〔３〕 Intermediate production method [3]

Figure JPOXMLDOC01-appb-C000015
Figure JPOXMLDOC01-appb-C000015

（式中、Ｒ3-a、Ｒ１２は前述の通りである。Ｒ3-bはC1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、Yで置換されてもよいフェニルを示す。）
　上記反応は、チエニルハライド（Ｖ－a）とホウ素誘導体との鈴木カップリングにより化合物（Ｖ－b）を合成する反応である。使用するパラジウム触媒としては、一般に鈴木カップリング反応で使用されるものであればよく、例えば、Pd2(dba)3、Pd(PPh3)4、Pd(dppf)2Cl2、Pd(OAc)2などが挙げられ、必要に応じて配位子の存在下に行うことができる。配位子としては、例えば、トリフェニルホスフィン、トリシクロヘキシルホスフィン、トリターシャリーブチルホスフィンのようなものが挙げられる。 Wherein R 3-a and R 12 are as described above. R 3-b is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl. C 3 -C 6 cycloalkyl optionally substituted with, halo C 1 -C 6 alkyl, phenyl optionally substituted with Y.)
The above reaction is a reaction for synthesizing the compound (Vb) by Suzuki coupling of thienyl halide (Va) and a boron derivative. As the palladium catalyst to be used, any catalyst generally used in the Suzuki coupling reaction may be used.For example, Pd 2 (dba) 3 , Pd (PPh 3 ) 4, Pd (dppf) 2 Cl 2, Pd (OAc) 2 and the like, and can be carried out in the presence of a ligand as necessary. Examples of the ligand include triphenylphosphine, tricyclohexylphosphine, and tritertiarybutylphosphine.

　また、上記反応で使用されるホウ素誘導体としては、一般に鈴木カップリングに使用されるものであればよく、例えば、トリエチルボランのようなトリアルキルボラン類、フェニルボロン酸、シクロプロピルボロン酸のようなボロン酸類、2-フェニル-4,4,5,5-テトラメチル-1,3,2-ジオキサボロランのようなボロン酸エステル類などが挙げられる。 The boron derivatives used in the above reaction may be those generally used for Suzuki coupling, for example, trialkylboranes such as triethylborane, phenylboronic acid, cyclopropylboronic acid and the like. Examples thereof include boronic acids and boronic acid esters such as 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；アセトニトリル、N, N-ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、１,４-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類；メタノール、エタノール、イソプロパノールのようなアルコール類；水などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, nitrobenzene and chlorobenzene; esters such as methyl acetate, ethyl acetate and propyl acetate. Aprotic polar solvents such as acetonitrile, N, N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA), sulfolane; diethyl ether, tertiary Examples include ethers such as butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane; alcohols such as methanol, ethanol and isopropanol; water and the like. As the solvent, one or more of these can be appropriately selected.

　上記反応は、必要に応じて塩基の存在下に行うことができる。例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのようなアルカリ金属炭酸塩；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩；炭酸カルシウム、炭酸バリウムのようなアルカリ土類金属炭酸塩；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物；水酸化カルシウム、水酸化バリウムのようなアルカリ土類金属水酸化物などが挙げられる。塩基としては、これらの1種又は2種以上を適宜選択、混合して使用することができる。 The above reaction can be performed in the presence of a base as necessary. For example, alkali metal carbonates such as sodium carbonate, potassium carbonate, and cesium carbonate; alkali metal carbonates such as sodium bicarbonate and potassium bicarbonate; alkaline earth metal carbonates such as calcium carbonate and barium carbonate; water Examples thereof include alkali metal hydroxides such as lithium oxide, sodium hydroxide, and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide. As the base, one or more of these may be appropriately selected and mixed for use.

　上記反応の反応温度は、通常０℃～１５０℃の範囲内、望ましくは室温から使用する溶媒の沸点までの範囲内、反応時間は、通常１分～４８時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually in the range of 0 ° C. to 150 ° C., desirably in the range from room temperature to the boiling point of the solvent used, and the reaction time is usually in the range of 1 minute to 48 hours.

　・中間体製造方法〔４〕 Intermediate production method [4]

Figure JPOXMLDOC01-appb-C000016
Figure JPOXMLDOC01-appb-C000016

（式中、Ｒ１、Ｒ１２は前述の通りである。Ｒ3-cはフッ素、塩素、臭素、ヨウ素を示し、Ｒ3-dは水素、塩素、フッ素、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、Yで置換されてもよいフェニルを示す。）
　上記反応は、チオフェン環α位をリチオ化した後、ハロゲン化剤によりチオフェン環α位をハロゲン化する反応である。使用するリチオ化試薬としては、ノルマルブチルリチウム、ターシャリーブチルリチウムのようなアルキルリチウム類、リチウムジイソプロピルアミド（LDA）のようなリチウムアミド類などが挙げられる。 (Wherein R 1 and R 12 are as defined above, R 3-c represents fluorine, chlorine, bromine and iodine, R 3-d represents hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted C 3 may be -C 6 cycloalkyl, halo C 1 -C 6 alkyl, phenyl which may be substituted by Y Show.)
The above reaction is a reaction in which the thiophene ring α-position is lithiated and then the thiophene ring α-position is halogenated with a halogenating agent. Examples of the lithiation reagent used include alkyllithiums such as normal butyllithium and tertiary butyllithium, and lithium amides such as lithium diisopropylamide (LDA).

　また、使用されるハロゲン化剤としては、1,2-ジブロモ-1,1,2,2-テトラクロロエタン、N-フルオロベンゼンスルホンイミド、ヨウ素などが挙げられる。 Further, examples of the halogenating agent to be used include 1,2-dibromo-1,1,2,2-tetrachloroethane, N-fluorobenzenesulfonimide, iodine and the like.

　上記反応に用いる溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、ノルマルヘキサン、ノルマルヘプタンのような炭化水素類；ジエチルエーテル、ターシャリーブチルメチルエーテル、１,４-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類；ジメチルプロピレンウレア(DMPU)；ヘキサメチルホスホラミド(HMPA)などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The solvent used in the above reaction may be any solvent as long as it is inert to the reaction. For example, hydrocarbons such as normal hexane and normal heptane; diethyl ether, tertiary butyl methyl ether and 1,4-dioxane. , Ethers such as tetrahydrofuran (THF) and 1,2-dimethoxyethane; dimethylpropylene urea (DMPU); hexamethylphosphoramide (HMPA) and the like. As the solvent, one or more of these can be appropriately selected.

　上記のリチオ化反応（工程４－１）の反応温度は、通常－８０℃～－２０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。また、ハロゲン化反応（工程４－２）の反応温度は、通常－８０℃～０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。 The reaction temperature of the above lithiation reaction (step 4-1) is usually in the range of −80 ° C. to −20 ° C., and the reaction time is usually in the range of 1 minute to 24 hours. In addition, the reaction temperature of the halogenation reaction (step 4-2) is usually in the range of −80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.

　また、上記反応は、必要に応じて、不活性ガスの下に行うことができる。当該不活性ガスとしては、例えば、アルゴンガス、窒素ガスなどが挙げられる。 In addition, the above reaction can be performed under an inert gas as necessary. Examples of the inert gas include argon gas and nitrogen gas.

　・中間体製造方法〔５〕 Intermediate production method [5]

Figure JPOXMLDOC01-appb-C000017
Figure JPOXMLDOC01-appb-C000017

（式中、Ｒ１、Ｒ１２は前述の通りである。）
　上記反応は、チオフェン環β位をハロゲン－リチウム交換反応によりリチオ化した後、フッ素化剤によりチオフェン環β位をフッ素化する反応である。使用するリチオ化試薬としては、中間体製造方法〔４〕と同様のリチオ化試薬が挙げられる。また、使用されるフッ素化剤としては、例えば、N-フルオロベンゼンスルホンイミドなどが挙げられる。 (Wherein R 1 and R 12 are as described above.)
The above reaction is a reaction in which the β-position of the thiophene ring is lithiated by a halogen-lithium exchange reaction and then the β-position of the thiophene ring is fluorinated by a fluorinating agent. Examples of the lithiation reagent to be used include the same lithiation reagents as in the intermediate production method [4]. Examples of the fluorinating agent used include N-fluorobenzenesulfonimide.

　上記反応で用いる溶媒としては、反応に不活性な溶媒であればどのような溶媒でもよく、例えば、中間体製造方法〔４〕に例示した溶媒と同様の溶媒が挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the intermediate production method [4]. As the solvent, one or more of these can be appropriately selected.

　上記のリチオ化反応（工程４－１）の反応温度は、通常－８０℃～－２０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。また、ハロゲン化反応（工程４－２）の反応温度は、通常－８０℃～０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。 The reaction temperature of the above lithiation reaction (step 4-1) is usually in the range of −80 ° C. to −20 ° C., and the reaction time is usually in the range of 1 minute to 24 hours. In addition, the reaction temperature of the halogenation reaction (step 4-2) is usually in the range of −80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.

　また、上記反応は、必要に応じて、不活性ガスの下に行うことができる。当該不活性ガスとしては、例えば、アルゴンガス、窒素ガスなどが挙げられる。 In addition, the above reaction can be performed under an inert gas as necessary. Examples of the inert gas include argon gas and nitrogen gas.

　・中間体製造方法〔６〕 Intermediate production method [6]

Figure JPOXMLDOC01-appb-C000018
Figure JPOXMLDOC01-appb-C000018

（式中、Ｒ１、Ｒ3-a、Ｒ3-b、Ｒ１２は前述の通りである。Ｒ3-eは水素、塩素、フッ素、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、Yで置換されてもよいフェニル又はシアノを示す。）
　上記反応は、チエニルハライド（ＩＶ－h）又は（ＩＶ－j）とホウ素誘導体との鈴木カップリングにより化合物（ＩＶ－i）又は（ＩＶ－k）をそれぞれ合成する反応であり、通常用いられる鈴木カップリング反応の条件に従い、又は中間体製造方法〔３〕に準じて行うことができる。 (Wherein R 1 , R 3-a , R 3-b and R 12 are as described above. R 3-e is hydrogen, chlorine, fluorine, C 1 -C 6 alkyl, C 2 -C 6 alkenyl. , C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted optionally C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 (Alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, phenyl or cyano optionally substituted with Y)
The above reaction is a reaction for synthesizing compound (IV-i) or (IV-k) by Suzuki coupling of thienyl halide (IV-h) or (IV-j) and a boron derivative, respectively. It can be performed according to the coupling reaction conditions or according to the intermediate production method [3].

　・中間体製造方法〔７〕 Intermediate production method [7]

Figure JPOXMLDOC01-appb-C000019
Figure JPOXMLDOC01-appb-C000019

（式中、Ｒ１、Ｒ3-d、Ｒ１２は前述の通りである。）
　上記反応は、チオフェン環α位をリチオ化した後、ホルミル化することでアルデヒド体（ＩＶ－i）を合成し、続いてフッ素化剤によりジフルオロメチル体（ＩＶ－m）に変換する反応である。
製造方法〔７〕の各工程について、以下に詳述する。 (In the formula, R 1 , R 3-d and R 12 are as described above.)
The above reaction is a reaction in which the thiophene ring α-position is lithiated and then formylated to synthesize an aldehyde (IV-i), and then converted to a difluoromethyl (IV-m) with a fluorinating agent. .
Each process of manufacturing method [7] is explained in full detail below.

　・製造方法〔７－１〕
　　　一般式（ＩＶ－d）→　一般式（ＩＶ－l）
　上記反応で使用するリチオ化剤としては、中間体製造方法〔４〕と同様のリチオ化剤が挙げられる。また、ホルミル化剤としては、例えば、N, N-ジメチルホルムアミド（DMF）などが挙げられる。 ・ Production method [7-1]
General formula (IV-d) → General formula (IV-l)
Examples of the lithiating agent used in the above reaction include the same lithiating agent as in the intermediate production method [4]. Examples of the formylating agent include N, N-dimethylformamide (DMF).

　上記反応で用いる溶媒としては、反応に不活性な溶媒であればどのような溶媒でもよく、例えば、中間体製造方法〔４〕に例示した溶媒と同様の溶媒が挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The solvent used in the above reaction may be any solvent as long as it is inert to the reaction, and examples thereof include the same solvents as those exemplified in the intermediate production method [4]. As the solvent, one or more of these can be appropriately selected.

　上記のリチオ化反応（工程７－１）の反応温度は、通常－８０℃～－２０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。また、ホルミル化反応（工程７－２）の反応温度は、通常－８０℃～０℃の範囲内、反応時間は、通常１分～２４時間の範囲内で行うことができる。 The reaction temperature of the above lithiation reaction (Step 7-1) is usually within a range of −80 ° C. to −20 ° C., and the reaction time is usually within a range of 1 minute to 24 hours. In addition, the reaction temperature of the formylation reaction (step 7-2) is usually in the range of −80 ° C. to 0 ° C., and the reaction time is usually in the range of 1 minute to 24 hours.

　また、上記反応は、必要に応じて、不活性ガスの下に行うことができる。当該不活性ガスとしては、例えば、アルゴンガス、窒素ガスなどが挙げられる。 In addition, the above reaction can be performed under an inert gas as necessary. Examples of the inert gas include argon gas and nitrogen gas.

　・製造方法〔７－２〕
　　　一般式（ＩＶ－l）→　一般式（ＩＶ－m）
　上記反応で、使用されるフッ素化剤としては、例えば、三フッ化ジエチルアミノ硫黄（DAST）などが挙げられる。 ・ Production method [7-2]
General formula (IV-l) → General formula (IV-m)
Examples of the fluorinating agent used in the above reaction include diethylaminosulfur trifluoride (DAST).

　上記反応は、必要に応じて溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；アセトニトリル、N, N-ジメチルホルムアミド（DMF）、ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）のような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、１,４-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類などが挙げられる。溶媒としては、これらの1種又は2種以上を適宜選択することができる。 The above reaction can be performed in the presence of a solvent, if necessary. Any solvent may be used as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, carbon tetrachloride; benzene, toluene, xylene, nitrobenzene, chlorobenzene Aromatic hydrocarbons such as; esters such as methyl acetate, ethyl acetate, propyl acetate; acetonitrile, N, N-dimethylformamide (DMF), dimethylacetamide (DMA), hexamethylphosphoric triamide (HMPA) And aprotic polar solvents such as: ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF) and 1,2-dimethoxyethane. As the solvent, one or more of these can be appropriately selected.

　上記反応の反応温度は、通常－２０℃～５０℃の範囲内、望ましくは０℃～室温までの範囲内、反応時間は、通常１分～４８時間の範囲内で行うことができる。 The reaction temperature for the above reaction is usually in the range of −20 ° C. to 50 ° C., desirably in the range of 0 ° C. to room temperature, and the reaction time is usually in the range of 1 minute to 48 hours.

　本発明に係る化合物は、除草剤の有効成分として使用した場合に、優れた除草効果を示す。その適用範囲は、水田、畑地、果樹園、桑園などの農耕地、山林、農道、グランド、工場敷地などの非農耕地と多岐にわたり、適用方法も土壌処理、茎葉処理、湛水処理等を適宜選択できる。 The compound according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. The range of application ranges widely from agricultural fields such as paddy fields, upland fields, orchards, mulberry fields, and non-agricultural land such as forests, farm roads, grounds, and factory sites. Applicable methods include soil treatment, foliage treatment, and flooding treatment as appropriate. You can choose.

　本発明に係る化合物は、一年生雑草や多年生雑草などの広範囲の望ましくない植物を防除することができる。具体的には、例えばイヌビエ又はタイヌビエ(barnyardgrass (Echinochloa crus-galli L.、Echinochloa oryzicola vasing.))、メヒシバ(crabgrass (Digitaria sanguinalis L.、Digitaria ischaemum Muhl. 、Digitaria adscendens Henr. 、Digitaria microbachne Henr. 、Digitaria horizontalis Willd.))、エノコログサ(greenfoxtail (Setaria viridis L.))、アキノエノコログサ(giant foxtail (Setaria faberi
Herrm.))、キンエノコロ(yellow foxtail (Setaria lutescens Hubb.))、オヒシバ(goosegrass (Eleusine indica L.))、カラスムギ(wild oat (Avena fatua L.))、セイバンモロコシ(johnsongrass (Sorghum halepense L.))、シバムギ(quackgrass (Agropyron repens L.))、ビロードキビ(alexandergrass (Brachiaria plantaginea))、ギネアキビ（guineagrass(Panicummaximum Jacq.)）、パラグラス(paragrass (Panicum purpurascens))、アゼガヤ(sprangletop (Leptochloa chinensis))、イトアゼガヤ(red sprangletop (Leptochloa panicea))、スズメノカタビラ(annual bluegrass (Poa annua L.))、スズメノテッポウ(black grass (Alopecurus myosuroides Huds.))、カモジグサ(cholorado bluestem (Agropyron tsukushiense (Honda) Ohwi))、メリケンニクキビ(broadleaf signalgrass(Brachiaria platyphylla Nash))、シンクリノイガ(southern sandbur (Cenchrus echinatus L.))、ネズミムギ(italian ryegrass (Lolium multiflorum Lam.))、ギョウギシバ(bermudagrass (Cynodon dactylon Pers.))のようなイネ科雑草(gramineae)；コゴメガヤツリ(rice flatsedge (Cyperusiria L.))、ハマスゲ(purple nutsedge (Cyperus rotundusL.))、キハマスゲ(yellow nutsedge (Cyperus esculentusL.))、ホタルイ(Japanese bulrush (Scirpus juncoides))、ミズガヤツリ(flatsedge (Cyperus serotinus))、タマガヤツリ(small-flower umbrellaplant (Cyperus difformis))、マツバイ(slender spikerush (Eleocharis acicularis))、クログワイ(water chestnut (Eleocharis kuroguwai))のようなカヤツリグサ科雑草(cyperaceae)；ウリカワ(Japanese ribbon waparo (Sagittariapygmaea))、オモダカ(arrow-head (Sagittaria trifolia))、ヘラオモダカ(narrowleaf waterplantain (Alisma canaliculatum))のようなオモダカ科雑草(alismataceae)；コナギ(monochoria (Monochoriavaginalis))、ミズアオイ(monochoria species (Monochoriakorsakowii))のようなミズアオイ科雑草(pontederiaceae)；アゼナ(false pimpernel (Lindernia pyxidaria))のようなアゼトウガラシ科雑草、アブノメ(abunome (Dopatrium junceum))のようなオオバコ科雑草(plantaginaceae)；キカシグサ(toothcup (Rotalaindia))、ヒメミソハギ(red stem (Ammanniamultiflora))のようなミソハギ科雑草(lythraceae)；ミゾハコベ(long stem waterwort(Elatine triandra SCHK.))のようなミゾハコベ科雑草(elatinaceae)；イチビ(velvetleaf (Abutilon theophrastiMEDIC.))、アメリカキンゴジカ(prickly sida (Sida spinosaL.))のようなアオイ科雑草(malvaceae)；オナモミ(common cocklebur (Xanthiumstrumarium L.))、ブタクサ(common ragweed (Ambrosiaelatior L.))、エゾノキツネアザミ(thistle (Breea setosa(BIEB.) KITAM.))、ハキダメギク(hairy galinsoga(Galinsogaciliata Blake)) 、カミツレ(wild chamomile(Matricariachamomilla L.))、ホトケノザ(henbit (Lamium amplexicauleL.))のようなキク科雑草(compositae)；イヌホウズキ(black nightshade (Solanumnigrum L.))、シロバナチョウセンアサガオ(jimsonweed (Daturastramonium))のようなナス科雑草(solanaceae)；アオビユ(slender amaranth (Amaranthusviridis L.))、アオゲイトウ(redroot pigweed (Amaranthusretroflexus L.))のようなヒユ科雑草(amaranthaceae)；サナエタデ(pale smartweed (Polygonumlapathifolium L.))、ハルタデ（ladysthumb(Polygonumpersicaria L.)）、ソバカズラ(wild buckwheat(Polygonumconvolvulus L.)) 、ミチヤナギ(knotweed(Polygonumaviculare L.))のようなタデ科雑草（polygonaceeae）；タネツケバナ(flexuous bittercress (Cardamineflexuosa WITH.))、ナズナ（shepherd’s-purse(Capsella bursa-pastoris Medik.)）、セイヨウカラシナ(indian mustard(Brassica juncea Czern.))のようなアブラナ科雑草（cruciferae）；マルバアサガオ(tall morningglory (IpomoeapurpureaL.))、セイヨウヒルガオ(field bindweed (ConvolvulusarvensisL.))、アメリカアサガオ（ivyleaf morningglory (IpomoeahederaceaJacq.)）のようなヒルガオ科雑草(convolvulaceae)；シロザ(common lambsquarters (Chenopodium album L.)) 、ホウキギ(mexican burningbush(Kochia scoparia Schrad.))のようなヒユ科雑草（Amaran thaceae）；スベリヒユ(common purslane (PortulacaoleraceaL.))のようなスベリヒユ科雑草（Portulacaceae）；エビスグサ(sicklepod (Cassia obtusifolia L.))のようなマメ科雑草（fabaceae）；ハコベ(common chickweed (StellariamediaL.))のようなナデシコ科雑草（caryophyllaceae）；ヤエムグラ(catchweed (Galium spurium L.))のようなアカネ科雑草（rubiaceae）；エノキグサ(threeseeded copperleaf (AcalyphaaustralisL.))のようなトウダイグサ科雑草（euphorbiaceae）；ツユクサ（common dayflower (Commelina communis L.)）のようなツユクサ科雑草（Commelinaceae）などの各種有害雑草を防除することができる。よって、有用作物、例えばトウモロコシ(corn (Zea mays L.))、ダイズ(soybean (Glycine max Merr.))、ワタ (cotton (Gossypiumspp.))、コムギ(wheat (Triticumspp.))、イネ(rice (Oryzasativa L.))、オオムギ(barley (Hordeum VulgareL.))、ライムギ(rye(Secalecereale L.))、エンバク(oat (Avena sativaL.))、ソルガム(sorgo (Sorghum bicolor Moench))、アブラナ(rape (Brassicanapus L.))、ヒマワリ(sunflower (Helianthus annuusL.))、テンサイ(suger beet (Beta Vulgaris L.))、サトウキビ(suger cane (Saccharum officinarum L.))、芝(japanese lawngrass (Zoysia japonica stend))、ピーナッツ(peanut (Arachis hypogaea L.))、アマ(flax (Linum usitatissimum L.))、タバコ(tobacco (Nicotiana tabacum L.))、コーヒー(coffee (Coffea spp.))などの栽培において、選択的に有害雑草を防除する場合或いは非選択的に有害雑草を防除する場合において有効に使用される。 The compounds according to the present invention can control a wide range of undesirable plants such as annual and perennial weeds. Specifically, for example, barnyardgrass (Echinochloa crus-galli L., Echinochloa oryzicola vasing.)), Barkyard (crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr. Digitaria horizontalis Willd.)), Enokorogusa (greenfoxtail (Setaria viridis L.)), Akinoenokorosa (giant foxtail (Setaria faberi)
Herrm.)), Yellow foxtail (Setaria lutescens Hubb.), Canopy (goosegrass (Eleusine indica L.)), oats (wild oat (Avena fatua L.)), sardine sorghum (johnsongrass (Sorghum halepense L.)) ), Buckwheat (quackgrass (Agropyron repens L.)), velvet millet (alexandergrass (Brachiaria plantaginea)), guineagrass (guineagrass (Panicummaximum Jacq.)), Paragrass (paragrass (Panicum purpurascens)), azegaya (spr), Red sprangletop (Leptochloa panicea), Japanese bluegrass (Poa annua L.), Japanese grass (Alopecurus myosuroides Huds.)), Blackbird (cholorado bluestem (Agropyron) Millet (broadleaf signalgrass (Brachiaria platyphylla Nash)), Thingrinoiga (southern sandbur (Cenchrus echinatus L.)), Rattus (italian ryegrass (Lolium multiflorum Lam.)), Gorilla (bermud) Gramineae weed (gramineae) such as agrass (Cynodon dactylon Pers.); rice flatsedge (Cyperusiria L.)), yellow nutsedge (Cyperus rotundusL.)), yellow nutsedge (Cyperus esculentusL. Firefly Cyperaceae such as); Urikawa (Japanese ribbon waparo (Sagittariapygmaea)), Omodaka (arrow-head (Sagittaria trifolia)), Heramodaka (narrowleaf waterplantain (Alisma canaliculatum)) ; Weeping (monochoria (Monochoriavaginalis)), squirrel (monochoria species (Monochoriakorsakowii)), weeds (pontederiaceae); azena (false pimpernel (Linderni a pyxidaria)), Abunome (Dopatrium junceum) psyllium weed (plantaginaceae); Weeds (lythraceae); Eelineaceae such as long stem waterwort (Elatine triandra SCHK.); Velvetleaf (Abutilon theophrastiMEDIC.), Prickly sida (Sida spinosa L.) Such as malvaceae; common fowl (common cocklebur (Xanthiumstrumarium L.)), ragweed (common ragweed (Ambrosiaelatior L.)), red fox thistle (thistle (Breea setosa (BIEB.) KITAM.)) hairy galinsoga (Galinsogaciliata Blake)), chamomile (wild chamomile (Matricariachamomilla L.)), henbit (Lamium amplexicaule L.), Compositae; black nightshade (Solanumnigrum L.), Solanum weed (solanaceae) such as jimsonweed (Daturastramonium); Amaranth (Amaranthusviridis L.), Amaranthaceae (redroot pigweed (Amaranthusretroflexus L.)) Polygonumaceae (such as Pale smartweed (Polygonumlapathifolium L.)), Hartade (ladysthumb (Polygonumpersicaria L.)), Buckwheat (wild buckwheat (Polygonumconvolvulus L.)), Polygonaceae (Knotweed (Polygonumaviculare L.)) Cruciferae, such as cruciferae (flexuous bittercress (Cardamineflexuosa WITH.)), Mushrooms (shepherd's-purse (Capsella bursa-pastoris Medik.)), Mustard (Brassica juncea Czern.); Morning glory (tall morningglory (IpomoeapurpureaL.)), Morning glory (field bindweed (ConvolvulusarvensisL.)), American morning glory (ivyleaf morningglory (IpomoeahederaceaJacq. Convolvulaceae, such as)); common lambsquarters (Chenopodium album L.), cypress (Amaran thaceae) such as broom (Amaran thaceae); common purslane (PortulacaoleraceaL.)), Such as Portulacaceae; leguminous weeds (sicklepod (Cassia obtusifolia L.)); fabaceae; common chickweed (StellariamediaL.) (Caryophyllaceae); Rubiaceae weeds such as catchweed (Galium spurium L.); Euphorbiaceae such as threeseeded copperleaf (AcalyphaaustralisL.); It is possible to control various harmful weeds such as Commelinaceae such as L.)). Therefore, useful crops such as corn (corn (Zea mays L.)), soybean (soybean (Glycine max Merr.)), Cotton (cotton (Gossypiumspp.)), Wheat (wheat (Triticumspp.)), Rice (rice ( Oryzasativa L.), barley (barde (Hordeum Vulgare L.)), rye (rye (Secalecereale L.)), oat (oat (Avena sativa L.)), sorghum (sorgo (Sorghum bicolor Moench)), rape (rape ( Brassicanapus L.)), sunflower (sunflower (Helianthus annuus L.)), sugar beet (suger beet (Beta Vulgaris L.)), sugar cane (suger cane (Saccharum officinarum L.)), turf (japanese lawngrass (Zoysia japonica stend)) , Peanut (peanut (Arachis hypogaea L.)), flax (Linum usitatissimum L.), tobacco (tobacco (Nicotiana tabacum L.)), coffee (coffee (Coffea spp.)), Etc. It is effectively used when controlling harmful weeds or when controlling harmful weeds non-selectively.

　本発明に係る化合物は、通常各種農業上の補助剤と混合して粉剤、粒剤、顆粒水和剤、水和剤、錠剤、丸剤、カプセル剤（水溶性フィルムで包装する形態を含む）、水性懸濁剤、油性懸濁剤、マイクロエマルジョン製剤、サスポエマルジョン製剤、水溶剤、乳剤、液剤、ペースト剤などの形態に製剤調製し、施用することができるが、本発明の目的に適合するかぎり、通常の当該分野で用いられているあらゆる製剤形態にすることができる。 The compound according to the present invention is usually mixed with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, tablets, pills, capsules (including forms packaged with water-soluble films). , Aqueous suspension, oil suspension, microemulsion formulation, suspoemulsion formulation, aqueous solvent, emulsion, solution, paste, etc. can be prepared and applied, but fits the purpose of the present invention As long as it is, it can be in any formulation form commonly used in the art.

　製剤に使用する補助剤としては、珪藻土、消石灰、炭酸カルシウム、タルク、ホワイトカーボン、カオリン、ベントナイト、カオリナイト及びセリサイトの混合物、クレー、炭酸ナトリウム、重曹、芒硝、ゼオライト、澱粉などの固形担体；水、トルエン、キシレン、ソルベントナフサ、ジオキサン、アセトン、イソホロン、メチルイソブチルケトン、クロロベンゼン、シクロヘキサン、ジメチルスルホキシド、ジメチルホルムアミド、ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、アルコールなどの溶剤；脂肪酸塩、安息香酸塩、アルキルスルホコハク酸塩、ジアルキルスルホコハク酸塩、ポリカルボン酸塩、アルキル硫酸エステル塩、アルキル硫酸塩、アルキルアリール硫酸塩、アルキルジグリコールエーテル硫酸塩、アルコール硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アリールスルホン酸塩、リグニンスルホン酸塩、アルキルジフェニルエーテルジスルホン酸塩、ポリスチレンスルホン酸塩、アルキルリン酸エステル塩、アルキルアリールリン酸塩、スチリルアリールリン酸塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸エステル塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルアリールリン酸エステル塩、ポリオキシエチレンアリールエーテルリン酸エステル塩、ナフタレンスルホン酸塩ホルマリン縮合物、アルキルナフタレンスルホン酸塩ホルマリン縮合物のような陰イオン系の界面活性剤や展着剤；ソルビタン脂肪酸エステル、グリセリン脂肪酸エステル、脂肪酸ポリグリセライド、脂肪酸アルコールポリグリコールエーテル、アセチレングリコール、アセチレンアルコール、オキシアルキレンブロックポリマー、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルアリールエーテル、ポリオキシエチレングリコールアルキルエーテル、ポリエチレングリコール、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油、ポリオキシプロピレン脂肪酸エステルのような非イオン系の界面活性剤や展着剤；オリーブ油、カポック油、ひまし油、シュロ油、椿油、ヤシ油、ごま油、トウモロコシ油、米ぬか油、落花生油、綿実油、大豆油、菜種油、亜麻仁油、きり油、液状パラフィンなどの植物油や鉱物油などが挙げられる。これら補助剤は本発明の目的から逸脱しないかぎり、1種又は2種以上を適宜選択して使用することができ、また、例えば、増量剤、増粘剤、沈降防止剤、凍結防止剤、分散安定剤、薬害軽減剤、防黴剤、発泡剤、崩壊剤、結合剤など、通常使用される各種補助剤も使用することができる。本発明に係る化合物と各種補助剤との配合割合は、0.1：99.9～95：5、望ましくは0.2：99.8～85：15である。 Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoic acid Salt, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol Sulfate ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester, alkyl aryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate Salt, polyoxyethylene aryl ether phosphate ester salt, naphthalene sulfonate formalin condensate, alkyl naphthalene sulfonate formalin condensate Surfactants and spreading agents; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl Aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene Nonionic surfactants and spreading agents such as fatty acid esters; olive oil, kapok oil, Examples include vegetable oils and mineral oils such as castor oil, palm oil, straw oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, persimmon oil, and liquid paraffin. These adjuvants can be used by appropriately selecting one or two or more kinds without departing from the object of the present invention. For example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion agents Various commonly used adjuvants such as stabilizers, safeners, antifungal agents, foaming agents, disintegrating agents, binders and the like can also be used. The compounding ratio of the compound according to the present invention and various adjuvants is 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.

　本発明に係る化合物を含有する除草剤の施用量（除草有効量）は、気象条件、土壌条件、製剤形態、対象となる望ましくない植物の種類、施用時期などの相違により一概に規定できないが、一般に１ヘクタール当り本発明に係る化合物が0.1～5,000ｇ、望ましくは0.5～3,000ｇ、更に望ましくは1～1,000ｇとなるように施用する。本発明には、このような除草剤の施用による望ましくない植物の防除方法も含まれる。 The application rate (herbicidally effective amount) of the herbicide containing the compound according to the present invention cannot be defined unconditionally due to differences in weather conditions, soil conditions, formulation forms, types of undesirable plants targeted, application time, etc. In general, the amount of the compound according to the present invention is 0.1 to 5,000 g, preferably 0.5 to 3,000 g, more preferably 1 to 1,000 g per hectare. The present invention also includes a method for controlling undesirable plants by applying such herbicides.

　また、本発明に係る化合物を含有する除草剤は、他の農薬、肥料、薬害軽減剤などと混用或いは併用することができ、この場合に一層優れた効果、作用性を示すことがある。他の農薬としては、除草剤、殺菌剤、抗生物質、植物ホルモン、殺虫剤などが挙げられる。特に、本発明に係る化合物と、他の除草剤の有効成分である化合物の１種又は２種以上とを混用或いは併用した混合除草性組成物は、適用草種の範囲、薬剤処理の時期、除草活性等を好ましい方向へ改良することが可能である。尚、本発明に係る化合物と他の除草剤の有効成分である化合物は、各々別々に製剤したものを散布時に混合して使用しても、両者を一緒に製剤して使用してもよい。本発明には、上記した混合除草性組成物も含まれる。 In addition, the herbicide containing the compound according to the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners and the like, and in this case, more excellent effects and activities may be exhibited. Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like. In particular, the mixed herbicidal composition in which the compound according to the present invention and one or more compounds as active ingredients of other herbicides are used in combination or in combination, the range of the applicable herbaceous species, the timing of drug treatment, It is possible to improve the herbicidal activity and the like in a preferable direction. In addition, the compound which is the active ingredient of the compound which concerns on this invention and another herbicide may mix and use it at the time of dispersion | distribution, respectively, or may use both together. The above-mentioned mixed herbicidal composition is also included in the present invention.

　本発明に係る化合物と他の除草剤の有効成分である化合物との混合比は、気象条件、土壌条件、薬剤の製剤形態、施用時期、施用方法などの相違により一概に規定できないが、本発明に係る化合物１重量部に対し、他の除草剤は有効成分である化合物を１種あたり0.001～10,000重量部、望ましくは0.01～1,000重量部配合する。また、施用適量は１ヘクタール当りの有効成分の総化合物量として0.1～10,000ｇ、望ましくは0.2～5,000ｇ、更に望ましくは10～3,000ｇである。本発明には、このような混合除草組成物の施用による望ましくない植物の防除方法も含まれる。 The mixing ratio between the compound according to the present invention and the compound that is an active ingredient of other herbicides cannot be defined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application time, application method, etc. Other herbicides are compounded in an amount of 0.001 to 10,000 parts by weight, preferably 0.01 to 1,000 parts by weight, as an active ingredient for other herbicides. The appropriate amount to be applied is 0.1 to 10,000 g, preferably 0.2 to 5,000 g, more preferably 10 to 3,000 g as the total amount of active ingredients per hectare. The present invention also includes a method for controlling undesirable plants by application of such a mixed herbicidal composition.

　他の除草剤の有効成分である化合物としては、下記化合物（一般名；一部ＩＳＯ申請中を含む）を例示することができるが、特に記載がない場合であっても、これら化合物に塩、アルキルエステル等が存在する場合は、当然それらも含まれる。 Examples of the compound that is an active ingredient of other herbicides include the following compounds (generic names; some of which are included in the application for ISO). If an alkyl ester or the like is present, it is naturally included.

　（１）２，４－Ｄ、２，４－Ｄブトチル（2,4-D-butotyl）、２，４－Ｄブチル（2,4-D-butyl）、２，４－Ｄジメチルアンモニウム（2,4-D-dimethylammonimum）、２，４－Ｄジオールアミン（2,4-D-diolamine）、２，４－Ｄエチル（2,4-D-ethyl）、２，４－Ｄ－２－エチルヘキシル（2,4-D-2-ethylhexyl）、２，４－Ｄイソブチル（2,4-D-isobutyl）、２，４－Ｄイソオクチル（2,4-D-isoctyl）、２，４－Ｄイソプロピル（2,4-D-isopropyl）、２，４－Ｄイソプロピルアンモニウム（2,4-D-isopropylammonium）、２，４－Ｄナトリウム（2,4-D-sodium）、２，４－Ｄイソプロパノールアンモニウム（2,4-D-isopropanolammonium）、２，４－Ｄトロールアミン（2,4-D-trolamine）、２，４－ＤＢ、２，４－ＤＢブチル（2,4-DB-butyl）、２，４－ＤＢジメチルアンモニウム（2,4-DB-dimethylammonium）、２，４－ＤＢイソオクチル（2,4-DB-isoctyl）、２，４－ＤＢカリウム（2,4-DB-potassium）、２，４－ＤＢナトリウム（2,4-DB-sodium）、ジクロロプロップ（dichlorprop）、ジクロロプロップブトチル（dichlorprop-butotyl）、ジクロロプロップジメチルアンモニウム（dichlorprop-dimethylammonium）、ジクロロプロップイソオクチル（dichlorprop-isoctyl）、ジクロロプロップカリウム（dichlorprop-potassium）、ジクロロプロップ－Ｐ（dichlorprop-P）、ジクロロプロップ－Ｐジメチルアンモニウム（dichlorprop-P-dimethylammonium）、ジクロロプロップ－Ｐカリウム（dichlorprop-P-potassium）、ジクロロプロップ－Ｐナトリウム（dichlorprop-P-sodium）、ＭＣＰＡ、ＭＣＰＡブトチル（MCPA-butotyl）、ＭＣＰＡジメチルアンモニウム（MCPA-dimethylammonium）、ＭＣＰＡ－２－エチルヘキシル（MCPA-2-ethylhexyl）、ＭＣＰＡカリウム（MCPA-potassium）、ＭＣＰＡナトリウム（MCPA-sodium）、ＭＣＰＡチオエチル（MCPA-thioethyl）、ＭＣＰＢ、ＭＣＰＢエチル（MCPB-ethyl）、ＭＣＰＢナトリウム（MCPB-sodium）、メコプロップ（mecoprop）、メコプロップブトチル（mecoprop-butotyl）、メコプロップナトリウム（mecoprop-sodium）、メコプロップ－Ｐ（mecoprop-P）、メコプロップ－Ｐブトチル（mecoprop-P-butotyl）、メコプロップ－Ｐジメチルアンモニウム（mecoprop-P-dimethylammonium）、メコプロップ－Ｐ－２－エチルヘキシル（mecoprop-P-2-ethylhexyl）、メコプロップ－Ｐカリウム（mecoprop-P-potassium）、ナプロアニリド（naproanilide）、クロメプロップ（clomeprop）のようなフェノキシ系化合物；２，３，６－ＴＢＡ、ジカンバ（dicamba）、ジカンバブトチル（dicamba-butotyl）、ジカンバジグリコールアミン（dicamba-diglycolamine）、ジカンバジメチルアンモニウム（dicamba-dimethylammonium）、ジカンバジオールアミン（dicamba-diolamine）、ジカンバイソプロピルアンモニウム（dicamba-isopropylammonium）、ジカンバカリウム（dicamba-potassium）、ジカンバナトリウム（dicamba-sodium）、ピクロラム（picloram）、ピクロラムジメチルアンモニウム（picloram-dimethylammonium）、ピクロラムイソオクチル（picloram-isoctyl）、ピクロラムカリウム（picloram-potassium）、ピクロラムトリイソプロパノールアンモニウム（picloram-triisopropanolammonium）、ピクロラムトリイソプロピルアンモニウム（picloram-triisopropylammonium）、ピクロラムトロールアミン（picloram-trolamine）、トリクロピル（triclopyr）、トリクロピルブトチル（triclopyr-butotyl）、トリクロピルトリエチルアンモニウム（triclopyr-triethylammonium）、クロピラリド（clopyralid）、クロピラリドオールアミン（clopyralid-olamine）、クロピラリドカリウム（clopyralid-potassium）、クロピラリドトリイソプロパノールアンモニウム（clopyralid-triisopropanolammonium）、アミノピラリド（aminopyralid）のような芳香族カルボン酸系化合物；その他、ナプタラム（naptalam）、ナプタラムナトリウム（naptalam-sodium）、ベナゾリン（benazolin）、ベナゾリンエチル（benazolin-ethyl）、キンクロラック（quinclorac）、キンメラック（quinmerac）、ダイフルフェンゾピル（diflufenzopyr）、ダイフルフェンゾピルナトリウム（diflufenzopyr-sodium）、フルオキシピル（fluroxypyr）、フルオキシピル－２－ブトキシ－１－メチルエチル（fluroxypyr-2-butoxy-1-methylethyl）、フルオキシピルメプチル（fluroxypyr-meptyl）、クロロフルレノール（chlorflurenol）、クロロフルレノールメチル（chlorflurenol-methyl）などのように植物のホルモン作用を攪乱することで除草効力を示すとされている化合物。 (1) 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium (2 , 4-D-dimethylammonimum), 2,4-D-diolamine (2,4-D-diolamine), 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D-2-ethylhexyl), 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl (2,4-D-isopropyl), 2,4-D-isopropylammonium, 2,4-D sodium (2,4-D-sodium), 2,4-D isopropanolammonium (2,4-D-isopropanolammonium), 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2 , 4-DB-dimethylammonium, 2,4-DB-iso Cutyl (2,4-DB-isoctyl), 2,4-DB potassium (2,4-DB-potassium), 2,4-DB sodium (2,4-DB-sodium), dichloroprop (dichlorprop), dichloro Propbutyl (dichlorprop-butotyl), dichloroprop-dimethylammonium, dichloroprop-isoctyl, dichloroprop-potassium, dichloroprop-P (dichloroprop-P), dichloroprop -Dichlorprop-P-dimethylammonium, dichloroprop-P-potassium, dichloroprop-P-sodium, MCPA, MCPA-butotyl, MCPA dimethyl Ammonium (MCPA-dimethylammonium), MCPA-2-ethylhexyl, MCPA Kaliu (MCPA-potassium), MCPA sodium (MCPA-sodium), MCPA-thioethyl, MCPB, MCPB ethyl (MCPB-ethyl), MCPB sodium (MCPB-sodium), mecoprop, mecoprop butyl ( mecoprop-butotyl), mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop- Phenoxy compounds such as P-2-ethylhexyl, mecoprop-P-potassium, naproanilide, clomeprop; 2,3,6-TBA , Dicamba, dicamba-butotyl, dicamba-diglycamine olamine), dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium , Picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram-triisopropanolammonium, Picloram-triisopropylammonium, picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr-triethylammonium, clopipyr-triethylammonium Aromatic carboxylic acid compounds such as clopyralid, clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium, aminopyralid; naptalam, sodium naptalam (naptalam-sodium), benazolin, benazolin-ethyl, quinclorac, quinmerac, diflufenzopyr, diflufenzopyr Sodium (diflufenzopyr-sodium), fluroxypyr (fluroxypyr), fluroxypyr-2-butoxy-1-methylethyl, fluroxypyr-meptyl, chloroflurenol (chlorflurenol) ), Chloroph A compound that has been shown to have herbicidal effects by disrupting the hormonal action of plants, such as chlorflurenol-methyl.

　（２）クロロトルロン(chlorotoluron)、ジウロン（diuron）、フルオメツロン(fluometuron)、リニュロン（linuron）、イソプロチュロン（isoproturon）、メトベンズロン（metobenzuron）、テブチウロン(tebuthiuron)、ジメフロン（dimefuron）、イソウロン（isouron）、カルブチレート（karbutilate）、メタベンズチアズロン（methabenzthiazuron）、メトクスロン（metoxuron）、モノリニュロン（monolinuron）、ネブロン（neburon）、シデュロン（siduron）、ターブメトン（terbumeton）、トリエタジン（trietazine）のような尿素系化合物；シマジン（simazine）、アトラジン（atrazine）、アトラトン（atratone）、シメトリン（simetryn）、プロメトリン（prometryn）、ジメタメトリン（dimethametryn）、ヘキサジノン(hexazinone)、メトリブジン（metribuzin）、ターブチラジン（terbuthylazine）、シアナジン（cyanazine）、アメトリン（ametryn）、シブトリン（cybutryne）、ターブトリン(terbutryn)、プロパジン（propazine）、メタミトロン（metamitron）、プロメトン（prometon）のようなトリアジン系化合物；ブロマシル（bromacil）、ブロマシルリチウム（bromacyl-lithium）、レナシル（lenacil）、ターバシル(terbacil)のようなウラシル系化合物；プロパニル（propanil）、シプロミッド（cypromid）のようなアニリド系化合物；スエップ（swep）、デスメディファム(desmedipham)、フェンメディファム（phenmedipham）のようなカーバメート系化合物；ブロモキシニル（bromoxynil）、ブロモキシニルオクタノエート（bromoxynil-octanoate）、ブロモキシニルヘプタノエート（bromoxynil-heptanoate）、アイオキシニル（ioxynil）、アイオキシニルオクタノエート（ioxynil-octanoate）、アイオキシニルカリウム（ioxynil-potassium）、アイオキシニルナトリウム（ioxynil-sodium）のようなヒドロキシベンゾニトリル系化合物；その他、ピリデート（pyridate）、ベンタゾン（bentazone）、ベンタゾンナトリウム（bentazone-sodium）、アミカルバゾン（amicarbazone）、メタゾール（methazole）、ペンタノクロール（pentanochlor）などのように植物の光合成を阻害することで除草効力を示すとされている化合物。 (2) chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, isouron Urea compounds such as karbutilate, methabenzthiazuron, metoxuron, monolinuron, neburon, siduron, terbumeton, trietazine; Simazine, atrazine, atratone, simetryn, promethrin, dimethametryn, hexazinone, metribuzin, terbuthylazine, cyanadi Triazine compounds such as (cyanazine), ametrin, cybutryne, terbutryn, propazine, metamitron, prometon; bromacil, bromacyl -lithium), uracil compounds such as lenacil, terbacil; anilide compounds such as propanil, cypromid; swep, desmedipham, fenmed Carbamate compounds such as phenmedipham; bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil, ioxynyloctano Ate (ioxynil-octanoate), ioxynil Hydroxybenzonitrile compounds such as ioxynil-potassium, ioxynil-sodium; other, pyridate, bentazone, bentazone-sodium, amicarbazone, Compounds such as methazole and pentanochlor that have been shown to have herbicidal activity by inhibiting plant photosynthesis.

　（３）それ自身が植物体中でフリーラジカルとなり、活性酸素を生成させて速効的な除草効力を示すとされているパラコート（paraquat）、ジクワット（diquat）のような４級アンモニウム塩系化合物。 (3) Quaternary ammonium salt compounds such as paraquat and diquat, which are said to themselves become free radicals in the plant body and generate active oxygen to show rapid herbicidal efficacy.

　（４）ニトロフェン（nitrofen）、クロメトキシフェン（chlomethoxyfen）、ビフェノックス（bifenox）、アシフルオルフェン（acifluorfen）、アシフルオルフェンナトリウム（acifluorfen-sodium）、ホメサフェン（fomesafen）、ホメサフェンナトリウム（fomesafen-sodium）、オキシフルオルフェン（oxyfluorfen）、ラクトフェン（lactofen）、アクロニフェン（aclonifen）、エトキシフェンエチル（ethoxyfen-ethyl、ＨＣ－２５２）、フルオログリコフェンエチル（fluoroglycofen-ethyl）、フルオログリコフェン（fluoroglycofen）のようなジフェニルエーテル系化合物；クロルフタリム（chlorphthalim）、フルミオキサジン（flumioxazin）、フルミクロラック（flumiclorac）、フルミクロラックペンチル（flumiclorac-pentyl）、シニドンエチル（cinidon-ethyl）、フルチアセットメチル（fluthiacet-methyl）のような環状イミド系化合物；その他、オキサジアルギル（oxadiargyl）、オキサジアゾン（oxadiazon）、スルフェントラゾン（sulfentrazone）、カルフェントラゾンエチル（carfentrazone-ethyl）、チジアジミン（thidiazimin）、ペントキサゾン（pentoxazone）、アザフェニジン（azafenidin）、イソプロパゾール（isopropazole）、ピラフルフェンエチル（pyraflufen-ethyl）、ベンズフェンジゾン（benzfendizone）、ブタフェナシル（butafenacil）、サフルフェナシル（saflufenacil）、フルアゾレート（fluazolate）、プロフルアゾール（profluazol）、フルフェンピルエチル（flufenpyr-ethyl）、ベンカルバゾン（bencarbazone）などのように植物のクロロフィル生合成を阻害し、光増感過酸化物質を植物体中に異常蓄積させることで除草効力を示すとされている化合物。 (4) Nitrofen, Chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium ), Oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl, HC-252, fluoroglycofen-ethyl, fluoroglycofen Diphenyl ether compounds; chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet-meth Cyclic imide compounds such as yl; other oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone , Azafenidin, isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, fluazolate, profluazole ( Inhibits plant chlorophyll biosynthesis, such as profluazol), flufenpyr-ethyl, and bencarbazone, and exhibits herbicidal effects by abnormally accumulating photosensitized peroxides in plants It is said that the compound.

　（５）ノルフルラゾン（norflurazon）、クロリダゾン（chloridazon）、メトフルラゾン（metflurazon）のようなピリダジノン系化合物；ピラゾリネート（pyrazolynate）、ピラゾキシフェン（pyrazoxyfen）、ベンゾフェナップ（benzofenap）、トプラメゾン(topramezone, BAS-670H)、ピラスルフォトール（pyrasulfotole）のようなピラゾール系化合物；その他、アミトロール(amitrole)、フルリドン（fluridone）、フルルタモン（flurtamone）、ジフルフェニカン（diflufenican）、メトキシフェノン（methoxyphenone）、クロマゾン（clomazone）、スルコトリオン（sulcotrione）、メソトリオン（mesotrione）、テンボトリオン（tembotrione）、テフリルトリオン（tefuryltrione, AVH-301）、ＫＵＨ－１１０、ＳＷ－０６５、イソキサフルトール（isoxaflutole）、ジフェンゾコート（difenzoquat）、ジフェンゾコートメチルサルフェート（difenzoquat-metilsulfate）、イソキサクロロトール（isoxachlortole）、ベンゾビシクロン（benzobicyclon）、ビシクロピロン（bicyclopyron）、ピコリナフェン（picolinafen）、ビフルブタミド（beflubutamid）などのようにカロチノイドなどの植物の色素生合成を阻害し、白化作用を特徴とする除草効力を示すとされている化合物。 (5) pyridazinone compounds such as norflurazon, chloridazon, metflurazon; pyrazolynate, pyrazoxifene, benzofenap, topramezone, BAS-670H, Pyrazole compounds such as pyrasulfotole; others, amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione ( sulcotrione, mesotrione, tembotrione, teboyltrione, AVH-301, KUH-110, SW-065, isoxaflutole, difenzoquat, diphen Pigment production of plants such as carotenoids such as coat methylsulfate (difenzoquat-metilsulfate), isoxachlortole, benzobicyclon, bicyclopyron, picolinafen, and biflubutamid A compound that inhibits synthesis and exhibits herbicidal activity characterized by whitening.

　（６）ジクロホップメチル（diclofop-methyl）、ジクロホップ（diclofop）、ピリフェノップナトリウム（pyriphenop-sodium）、フルアジホップブチル（fluazifop-butyl）、フルアジホップ（fluazifop）、フルアジホップ-Ｐ（fluazifop-P）、フルアジホップ－Ｐ－ブチル（fluazifop-P-butyl）、ハロキシホップメチル（haloxyfop-methyl）、ハロキシホップ（haloxyfop）、ハロキシホップエトチル（haloxyfop-etotyl）、ハロキシホップ－Ｐ（haloxyfop-P）、ハロキシホップ－Ｐ－メチル（haloxyfop-P-methyl）、キザロホップエチル（quizalofop-ethyl）、キザロホップ－Ｐ（quizalofop-P）、キザロホップ－Ｐ－エチル（quizalofop-P-ethyl）、キザロホップ－Ｐ－テフリル（quizalofop-P-tefuryl）、シハロホップブチル（cyhalofop-butyl）、フェノキサプロップエチル（fenoxaprop-ethyl）、フェノキサプロップ－Ｐ（fenoxaprop-P）、フェノキサプロップ－Ｐ－エチル（fenoxaprop-P-ethyl）、メタミホッププロピル（metamifop-propyl）、メタミホップ（metamifop）、クロジナホッププロパルギル（clodinafop-propargyl）、クロジナホップ（clodinafop）、プロパキザホップ（propaquizafop）のようなアリールオキシフェノキシプロピオン酸系化合物；アロキシジムナトリウム（alloxydim-sodium）、アロキシジム（alloxydim）、クレソジム（clethodim）、セトキシジム（sethoxydim）、トラルコキシジム（tralkoxydim）、ブトロキシジム（butroxydim）、テプラロキシジム（tepraloxydim）、プロホキシジム（profoxydim）、シクロキシジム（cycloxydim）のようなシクロヘキサンジオン系化合物；ピノキサデン（pinoxaden）のようなフェニルピラゾリン系化合物;などのように脂肪酸の生合成を阻害し、植物に除草効力を示すとされている化合物。 (6) Dicloofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P (fluazifop-P) , Fluazifop-P-butyl, Haloxyfop-methyl, Haloxyfop, Haloxyfop-etotyl, Haloxyfop-P, Haloxyhop -P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-ethyl (quizalofop-P-ethyl) quizalofop-P-tefuryl), cyhalofop-butyl, fenoxaprop-ethyl, phenoxaprop- (Fenoxaprop-P), fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop Aryloxyphenoxypropionic acid compounds such as propaquizafop; sodium alloxydim, alloxydim, clethodim, sethoxydim, tralkoxydim, butroxydim ), Cyclohexanedione compounds such as tepraloxydim, profoxydim, cycloxydim; phenylpyrazoline compounds such as pinoxaden; , Weeding plants Compounds are to exhibit a force.

　（７）クロリムロンエチル（chlorimuron-ethyl）、クロリムロン（chlorimuron）、スルホメツロンメチル（sulfometuron-methyl）、スルホメツロン（sulfometuron）、プリミスルフロンメチル（primisulfuron-methyl）、プリミスルフロン（primisulfuron）、ベンスルフロンメチル（bensulfuron-methyl）、ベンスルフロン（bensulfuron）、クロルスルフロン（chlorsulfuron）、メトスルフロンメチル（metsulfuron-methyl）、メトスルフロン（metsulfuron）、シノスルフロン（cinosulfuron）、ピラゾスルフロンエチル（pyrazosulfuron-ethyl）、ピラゾスルフロン（pyrazosulfuron）、フラザスルフロン（flazasulfuron）、リムスルフロン（rimsulfuron）、ニコスルフロン（nicosulfuron）、イマゾスルフロン（imazosulfuron）、フルセトスルフロン（flucetosulfuron）、シクロスルファムロン（cyclosulfamuron）、プロスルフロン（prosulfuron）、フルピルスルフロンメチルナトリウム（flupyrsulfuron-methyl-sodium）、フルピルスルフロン（flupyrsulfuron）、トリフルスルフロンメチル（triflusulfuron-methyl）、トリフルスルフロン（triflusulfuron）、ハロスルフロンメチル（halosulfuron-methyl）、ハロスルフロン（halosulfuron）、チフェンスルフロンメチル（thifensulfuron-methyl）、チフェンスルフロン（thifensulfuron）、エトキシスルフロン（ethoxysulfuron）、オキサスルフロン（oxasulfuron）、エタメトスルフロン（ethametsulfuron）、エタメトスルフロンメチル（ethametsulfuron-methyl）、イオドスルフロン（iodosulfuron）、イオドスルフロンメチルナトリウム（iodosulfuron-methyl-sodium）、スルフォスルフロン（sulfosulfuron）、トリアスルフロン（triasulfuron）、トリベヌロンメチル（tribenuron-methyl）、トリベヌロン（tribenuron）、トリトスルフロン（tritosulfuron）、フォーラムスルフロン（foramsulfuron）、トリフルオキシスルフロン（trifloxysulfuron）、トリフルオキシスルフロンナトリウム（trifloxysulfuron-sodium）、メソスルフロンメチル（mesosulfuron-methyl）、メソスルフロン（mesosulfuron）、オルソスルファムロン（orthosulfamuron）、アミドスルフロン（amidosulfuron）、プロピリスルフロン（propyrisulfuron、ＴＨ－５４７）、ＮＣ－６２０、国際公開公報WO2005092104号に記載されている化合物のようなスルホニルウレア系化合物；フルメツラム（flumetsulam）、メトスラム（metosulam）、ジクロスラム（diclosulam）、クロランスラムメチル（cloransulam-methyl）、フロラスラム（florasulam）、ペノクススラム(penoxsulam)、ピロクススラム（pyroxsulam）のようなトリアゾロピリミジンスルホンアミド系化合物；イマザピル（imazapyr）、イマザピルイソプロピルアンモニウム（imazapyr-isopropylammonium）、イマゼタピル（imazethapyr）、イマゼタピルアンモニウム（imazethapyr-ammonium）、イマザキン（imazaquin）、イマザキンアンモニウム（imazaquin-ammonium）、イマザモックス（imazamox）、イマザモックスアンモニウム（imazamox-ammonium）、イマザメタベンズ（imazamethabenz）、イマザメタベンズメチル（imazamethabenz-methyl）、イマザピック（imazapic）のようなイミダゾリノン系化合物；ピリチオバックナトリウム（pyrithiobac-sodium）、ビスピリバックナトリウム（bispyribac-sodium）、ピリミノバックメチル（pyriminobac-methyl）、ピリベンゾキシム（pyribenzoxim）、ピリフタリド（pyriftalid）、ピリミスルファン（pyrimisulfan, ＫＵＨ－０２１）、トリアファモン（triafamone,ＢＣＨ－１００）のようなピリミジニルサリチル酸系化合物；フルカーバゾン（flucarbazone）、フルカーバゾンナトリウム（flucarbazone-sodium）、プロポキシカーバゾンナトリウム（propoxycarbazone-sodium）、プロポキシカーバゾン（propoxycarbazone）のようなスルホニルアミノカルボニルトリアゾリノン系化合物；その他、グリホサート（glyphosate）、グリホサートナトリウム（glyphosate-sodium）、グリホサートカリウム（glyphosate-potassium）、グリホサートアンモニウム（glyphosate-ammonium）、グリホサートジアンモニウム（glyphosate-diammonium）、グリホサートイソプロピルアンモニウム（glyphosate-isopropylammonium）、グリホサートトリメシウム（glyphosate-trimesium）、グリホサートセスキナトリウム（glyphosate-sesquisodium）、グルホシネート（glufosinate）、グルホシネートアンモニウム（glufosinate-ammonium）、グルホシネート-Ｐ（glufosinate-Ｐ）、グルホシネート-Ｐアンモニウム（glufosinate-Ｐ-ammonium）、グルホシネート-Ｐナトリウム（glufosinate-Ｐ-sodium）、ビラナホス（bilanafos）、ビラナホスナトリウム（bilanafos-sodium）、シンメチリン（cinmethylin）などのように植物のアミノ酸生合成を阻害することで除草効力を示すとされている化合物。 (7) Chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, Bensulfuron-methyl, bensulfuron, chlorsulfuron, methsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl , Pyrazosulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, flucetosulfuron, cyclosulfamuron, prosulfur Prosulfuron, flupirsulfuron-methyl-sodium, flupirsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl , Halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethamethsulfuron methyl ( ethametsulfuron-methyl, iodosulfuron, sodium iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron (Tribenuron), tritosulfuron, trisulfoxyon (foramsulfuron), trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron Sulfonylurea compounds such as compounds described in, orthosulfamuron, amidosulfuron, propyrisulfuron (TH-547), NC-620, international publication WO2005092104; Triazolopyrimidine sulfones such as (flumetsulam), metosulam, diclosulam, cloransulam-methyl, florasulam, penoxsulam, pyroxsulam Amamide compounds; imazapyr, imazapyr-isopropylammonium, imazethapyr, imazethapyr-ammonium, imazaquin, imazaquin-ammonium, Imidazolinone compounds such as imazamox, imazamox-ammonium, imazamethabenz, imazamethabenz-methyl, imazapic; pyrithiobac- sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid, pyrimisulfan, KUH-021, triafamone, Pyrimidinyl salicylic acid compounds such as CH-100); sulfonylaminocarbonyltria such as flucarbazone, flucarbazone-sodium, propoxycarbazone-sodium, propoxycarbazone Zolinone compounds; other glyphosate, glyphosate sodium, glyphosate-sodium, glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate isopropylammonium (glyphosate) -isopropylammonium), glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate Glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, vilanafos, vilanafos sodium -sodium), compounds such as cinmethylin and the like, which are said to show herbicidal activity by inhibiting plant amino acid biosynthesis.

　（８）トリフルラリン（trifluralin）、オリザリン（oryzalin）、ニトラリン（nitralin）、ペンディメタリン（pendimethalin）、エタルフルラリン（ethalfluralin）、ベンフルラリン（benfluralin）、プロジアミン（prodiamine）、ブトラリン（butralin）、ジニトラミン（dinitramine）のようなジニトロアニリン系化合物；ベンスリド（bensulide）、ナプロパミド（napropamide）、プロピザミド（propyzamide、プロナミド（pronamide））のようなアミド系化合物；アミプロホスメチル（amiprofos-methyl）、ブタミホス（butamifos）、アニロホス（anilofos）、ピペロホス（piperophos）のような有機リン系化合物；プロファム（propham）、クロルプロファム（chlorpropham）、バーバン（barban）、カルベタミド（carbetamide）のようなフェニルカーバメート系化合物；ダイムロン（daimuron）、クミルロン（cumyluron）、ブロモブチド（bromobutide）、メチルダイムロン（methyldymron）のようなクミルアミン系化合物；その他、アシュラム（asulam）、アシュラムナトリウム（asulam-sodium）、ジチオピル（dithiopyr）、チアゾピル（thiazopyr）、クロルタールジメチル（chlorthal-dimethyl）、クロルタール（chlorthal）、ジフェナミド（diphenamid）、フラムプロップ－Ｍ－メチル（flamprop-M-methyl）、フラムプロップ－Ｍ（flamprop-M）、フラムプロップ－Ｍ－イソプロピル（flamprop-M-isopropyl）などのように植物の細胞有糸分裂を阻害することで除草効力を示すとされている化合物。 (8) Trifluralin, oryzalin, oryzalin, nitalin, pendimethalin, ethalluralin, benfluralin, prodiamine, butralin, dinitramine ( dinitroaniline compounds such as dinitramine; amide compounds such as bensulide, napropamide, propyzamide, pronamide; amiprofos-methyl, butamifos , Organophosphorus compounds such as anilofos, piperophos; phenyl carbamate compounds such as propham, chlorpropham, barban, carbetamide; daimuron ), Kumi Cumylamine compounds such as cumyluron, bromobutide, methyldymron; others, ashram, asuram-sodium, dithiopyr, thiazopyr, chlorotal dimethyl (Chlorthal-dimethyl), chlorthal, diphenamid, flamprop-M-methyl, flamprop-M, flamprop-M-flamprop-M -isopropyl) and other compounds that are said to show herbicidal efficacy by inhibiting plant cell mitosis.

　（９）アラクロール（alachlor）、メタザクロール（metazachlor）、ブタクロール（butachlor）、プレチラクロール（pretilachlor）、メトラクロール（metolachlor）、Ｓ－メトラクロール（S-metolachlor）、テニルクロール（thenylchlor）、ペトキサマイド(pethoxamid)、アセトクロール（acetochlor）、プロパクロール（propachlor）、ジメテナミド（dimethenamid）、ジメテナミド－Ｐ（dimethenamid－Ｐ）、プロピソクロール（propisochlor）、ジメタクロール（dimethachlor）のようなクロロアセトアミド系化合物；モリネート（molinate）、ジメピペレート（dimepiperate）、ピリブチカルブ（pyributicarb）、ＥＰＴＣ、ブチレート（butylate）、ベルノレート（vernolate）、ペブレート（pebulate）、シクロエート（cycloate）、プロスルホカルブ（prosulfocarb）、エスプロカルブ（esprocarb）、チオベンカルブ（thiobencarb）、ジアレート（diallate）、トリアレート（tri-allate）、オルベンカルブ（orbencarb）のようなチオカーバメート系化合物；その他、エトベンザニド（etobenzanid）、メフェナセット（mefenacet）、フルフェナセット（flufenacet）、トリディファン（tridiphane）、カフェンストロール（cafenstrole）、フェントラザミド（fentrazamide）、オキサジクロメフォン（oxaziclomefone）、インダノファン（indanofan）、ベンフレセート（benfuresate）、ピロキサスルフォン（pyroxasulfone）、フェノキサスルフォン（fenoxasulfone）、メチオゾリン（methiozolin）、ダラポン（dalapon）、ダラポンナトリウム（dalapon-sodium）、ＴＣＡナトリウム（TCA-sodium）、トリクロロ酢酸（trichloroacetic acid）などのように植物のタンパク質生合成あるいは脂質生合成を阻害することで除草効力を示すとされている化合物。 (9) Alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, tenylchlor, petoxaxide Chloroacetamide compounds such as acetochlor, acetochlor, propachlor, dimethenamid, dimethenamid-P, propisochlor, dimethachlor; molinate , Dimepiperate, pyributicarb, EPTC, butyrate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, thio Thiocarbamate compounds such as thiobencarb, dialate, diallate, tri-allate, orbencarb; etobenzanid, mefenacet, flufenacet, tri Didiphane, caffenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, fenoxasulfone, methiozoline To inhibit plant protein biosynthesis or lipid biosynthesis, such as methiozolin, dalapon, dalapon-sodium, TCA sodium (TCA-sodium), trichloroacetic acid. Compounds are to exhibit a herbicidal activity.

　（１０）ジクロベニル（dichlobenil）、トリアジフラム（triaziflam）、インダジフラム（indaziflam）、フルポキサム（flupoxam）などのように植物のセルロース生合成を阻害することで除草効力を示すとされている化合物。 (10) A compound that has been shown to have herbicidal activity by inhibiting cellulose biosynthesis in plants such as dichlobenil, triaziflam, indaziflam, and flupoxam.

　（１１）ＭＳＭＡ、ＤＳＭＡ、ＣＭＡ、エンドタール（endothall）、エンドタールジカリウム（endothall-dipotassium）、エンドタールナトリウム（endothall-sodium）、エンドタールモノ(Ｎ，Ｎ－ジメチルアルキルアンモニウム)（endothall-mono(N,N-dimethylalkylammonium)）、エトフメセート（ethofumesate）、ソディウムクロレート（sodium chlorate）、ペラルゴン酸（pelargonic acid、ノナン酸（nonanoic acid））、ホスアミン（fosamine）、ホスアミンアンモニウム（fosamine-ammonium）、イプフェンカルバゾン（ipfencarbazone、ＨＯＫ－２０１）、アクロレイン（aclolein）、スルファミン酸アンモニウム（ammonium sulfamate）、ボラックス（borax）、クロロ酢酸（chloroacetic acid）、クロロ酢酸ナトリウム（sodium chloroacete）、シアナミド（cyanamide）、メチルアルソン酸（methylarsonic acid）、ジメチルアルソン酸（dimethylarsinic acid）、ジメチルアルソン酸ナトリウム（sodium dimethylarsinate）、ジノターブ（dinoterb）、ジノターブアンモニウム（dinoterb-ammonium）、ジノターブジオールアミン（dinoterb-diolamine）、ジノターブアセテート（dinoterb-acetate）、ＤＮＯＣ、硫酸第一鉄（ferrous sulfate）、フルプロパネート（flupropanate）、フルプロパネートナトリウム（flupropanate-sodium）、イソキサベン（isoxaben）、メフルイジド（mefluidide）、メフルイジドジオールアミン（mefluidide-diolamine）、メタム（metam）、メタムアンモニウム（metam-ammonium）、メタムカリウム（metam-potassium）、メタムナトリウム（metam-sodium）、イソチオシアン酸メチル（methyl isothiocyanate）、ペンタクロロフェノール（pentachlorophenol）、ペンタクロロフェノールナトリウム（sodium pentachlorophenoxide）、ペンタクロロフェノールラウレート（pentachlorophenol laurate）、キノクラミン（quinoclamine）、硫酸（sulfuric acid）、ウレアサルフェート（urea sulfate）などのその他の除草剤。 (11) MSMA, DSMA, CMA, endothal (endothall), endothal-dipotassium, endothal sodium (endothall-sodium), endtal mono (N, N-dimethylalkylammonium) (endothall-mono ( N, N-dimethylalkylammonium)), etofumesate, sodium chlorate, pelargonic acid, nonanoic acid, fosamine, fosamine-ammonium, ipfen Carbazone (ipfencarbazone, HOK-201), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarson Acid (methylarsonic acid) , Dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate , DNOC, ferrous sulfate (flupropanate), flupropanate, sodium flupropanate (flupropanate-sodium), isoxaben, mefluidide, mefluidide-diolamine, Metam, metam-ammonium, metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, sodium pentachlorophenol ( sodium pent Other herbicides such as achlorophenoxide, pentachlorophenol laurate, quinoclamine, sulfuric acid, urea sulfate.

　（１２）ザントモナス　キャンペストリス（Xanthomonas campestris）、エピココロシルス　ネマトソルス（Epicoccosirus nematosorus）、エピココロシルス　ネマトスペラス（Epicoccosirus nematosperus）、エキセロヒラム　モノセラス（Exserohilum monoseras）、ドレクスレラ　モノセラス（Drechsrela monoceras）などのように植物に寄生することで除草効力を示すとされているもの。 (12) Xanthomonas campestris, Epicocorocillus nematosols (Epicoccosirus nematosorus), Epicocosirus nematosperus, Exserohilum monoslas, Exserohilum monoslas It is supposed to show herbicidal efficacy by doing.

　次に本発明の実施例を記載するが、本発明はこれらに限定されるものではない。まず、本発明に係る化合物の合成例を記載する。 Next, examples of the present invention will be described, but the present invention is not limited thereto. First, synthesis examples of the compounds according to the present invention will be described.

　・合成例１
1,1,1-トリフルオロ-N-(2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（化合物No.1-1）の合成
（１）窒素雰囲気下、3-アミノ-2-チオフェンカルボン酸メチル（7.86 g）、トリエチルアミン（6.93 ml）及びクロロホルム（200 ml）の溶液を0℃に冷却し、トリフルオロメタンスルホン酸無水物（8.20 ml）とクロロホルム（20 ml）との混合溶液を１５分かけて滴下した。室温まで昇温しながら、さらに２０時間攪拌した。反応溶液を水で洗浄し、水層をクロロホルムで抽出した。有機層を1つにまとめ、飽和食塩水で洗浄後、2 N水酸化ナトリウム水溶液（100 ml）で2回洗浄した。分離したアルカリ性水溶液を濃塩酸で酸性にした後、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、溶媒を減圧下で留去し、黄色固体（8.70 g）を得た。得られた黄色固体は、1H-NMRより、メチル 3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボキシレートと3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボン酸との混合物（約１：３）であることがわかった。 Synthesis example 1
Synthesis of 1,1,1-trifluoro-N- (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 1-1) (1) Nitrogen Under atmosphere, a solution of methyl 3-amino-2-thiophenecarboxylate (7.86 g), triethylamine (6.93 ml) and chloroform (200 ml) was cooled to 0 ° C, trifluoromethanesulfonic anhydride (8.20 ml) and chloroform (20 ml) was added dropwise over 15 minutes. The mixture was further stirred for 20 hours while raising the temperature to room temperature. The reaction solution was washed with water, and the aqueous layer was extracted with chloroform. The organic layers were combined, washed with saturated brine, and then washed twice with 2N aqueous sodium hydroxide solution (100 ml). The separated alkaline aqueous solution was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a yellow solid (8.70 g). The obtained yellow solid was analyzed by 1 H-NMR from a mixture of methyl 3- (trifluoromethylsulfonamido) thiophene-2-carboxylate and 3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid (approximately 1: 3).

　メチル 3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボキシレートの1H-NMRスペクトルデータを以下に示す。
1H-NMR　(500 MHz, acetone-d6, δppm): 3.92 (s, 3H), 7.35 (d, J=5.5 Hz, 1H), 7.94(d, J=5.5 Hz, 1H).
　3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボン酸の1H-NMRスペクトルデータを以下に示す。
1H-NMR　(500 MHz, CDCl3, δppm): 7.39 (d, J=5.5 Hz, 1H), 7.60 (d, J=5.5 Hz, 1H),9.94(br s, 1H).
（２）上記（１）で合成した混合物（8.70 g）をTHF（100 ml）に溶解させ、窒素雰囲気下、予め氷冷した水素化リチウムアルミニウム（3.86 g）とTHF（150 ml）の懸濁液に35分かけて滴下した。還流下で2時間攪拌し、冷却後氷冷下で水を加え反応を停止した。酢酸エチルと2 N塩酸水溶液を加え、しばらく攪拌した。水層を酢酸エチルで抽出し、有機層を合わせて飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去し、粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)メタンスルホンアミド（8.13 g）を得た。
（３）上記（２）で合成した粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)メタンスルホンアミド（1.36 g）をトルエン（58 ml）に溶解し、ｐ－トルエンスルホン酸一水和物（665 mg）と2－ピペリドン（723 mg）とを加えた。反応溶液を加熱し、Dean-Stark装置を用いて共沸脱水しながら3時間攪拌した。室温まで冷却後、酢酸エチルで希釈し、飽和食塩水で洗浄した。硫酸ナトリウムで乾燥した後、溶媒を減圧下で留去し、得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～１：１）で精製し、目的物（1.05 g、化合物No.1-1）を薄い褐色固体として得た。 The 1 H-NMR spectrum data of methyl 3- (trifluoromethylsulfonamido) thiophene-2-carboxylate is shown below.
1 H-NMR (500 MHz, acetone-d6, δppm): 3.92 (s, 3H), 7.35 (d, J = 5.5 Hz, 1H), 7.94 (d, J = 5.5 Hz, 1H).
The 1 H-NMR spectrum data of 3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid is shown below.
1 H-NMR (500 MHz, CDCl 3 , δppm): 7.39 (d, J = 5.5 Hz, 1H), 7.60 (d, J = 5.5 Hz, 1H), 9.94 (br s, 1H).
(2) The mixture (8.70 g) synthesized in (1) above was dissolved in THF (100 ml), and a suspension of lithium aluminum hydride (3.86 g) and THF (150 ml) that had been ice-cooled in advance under a nitrogen atmosphere. The solution was added dropwise over 35 minutes. The mixture was stirred for 2 hours under reflux, and after cooling, water was added under ice cooling to stop the reaction. Ethyl acetate and 2N aqueous hydrochloric acid solution were added, and the mixture was stirred for a while. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined, washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and crude 1,1,1-trifluoro-N- ( 2- (Hydroxymethyl) thiophen-3-yl) methanesulfonamide (8.13 g) was obtained.
(3) Crude 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophen-3-yl) methanesulfonamide (1.36 g) synthesized in (2) above was added to toluene (58 ml). After dissolution, p-toluenesulfonic acid monohydrate (665 mg) and 2-piperidone (723 mg) were added. The reaction solution was heated and stirred for 3 hours while performing azeotropic dehydration using a Dean-Stark apparatus. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 1: 1) to obtain the desired product (1.05 g, compound No. .1-1) was obtained as a light brown solid.

　・合成例２
イソブチル(2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)((トリフルオロメチル)スルホニル)カーバメート（化合物No.1-7）の合成
　1,1,1-トリフルオロ-N-(2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（210 mg）をトルエン（6 ml）に溶解させ、ピリジン（0.10 ml）とクロロギ酸イソブチル（0.16 ml）とを加えて、室温で17時間攪拌した。2 N塩酸水溶液を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～１：１）で精製し、目的物（218 mg、化合物No.1-7）を薄い褐色油状物質として得た。 Synthesis example 2
Synthesis of isobutyl (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 1-7) 1,1,1-trifluoro -N- (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (210 mg) was dissolved in toluene (6 ml), pyridine (0.10 ml) and chloroformate Isobutyl (0.16 ml) was added and stirred at room temperature for 17 hours. After 2 N hydrochloric acid aqueous solution was added to stop the reaction, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 1: 1) to obtain the desired product (218 mg, compound No. 1-7) as a pale brown oily substance.

　・合成例３
1,1,1-トリフルオロ-N-(4-メチル-2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（化合物No.13-1）の合成
（１）窒素雰囲気下、3-アミノ-4-メチルチオフェン-2-カルボン酸メチル（5.41 g）、トリエチルアミン（5.26 ml）及びクロロホルム（200 ml）の溶液を-4℃に冷却し、トリフルオロメタンスルホン酸無水物（10.7 g）とクロロホルム（20 ml）との混合溶液を２５分かけて滴下した。氷冷しながら、さらに１時間攪拌した後、水を加えて反応を停止した。水層をクロロホルムで抽出した。有機層を1つにまとめ、2 N水酸化ナトリウム水溶液（100 ml）で2回洗浄した。アルカリ水溶液を分離し、還流下で２０分攪拌した。室温まで冷却した後、濃塩酸を加え酸性にした。懸濁液を氷冷しながら攪拌し、生じた固体を濾過し、水で洗浄した後、減圧下で乾燥することで、4-メチル-3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボン酸を淡いピンク色固体（3.09 g）として得た。（融点164－166℃）1H-NMR　(500 MHz, CDCl3, δppm): 2.34 (s, 3H), 7.29 (s, 1H), 8.45(br s, 1H).
（２）上記（１）で得られた4-メチル-3-(トリフルオロメチルスルホンアミド)チオフェン-2-カルボン酸（2.82 g）をTHF（50 ml）に溶解させ、窒素雰囲気下、予め氷冷した水素化リチウムアルミニウム（1.15 g）とTHF（50 ml）の懸濁液に２０分かけて滴下した。還流下で１時間攪拌し、冷却後氷冷下で水を加え反応を停止した。酢酸エチルと2 N塩酸水溶液を加え、しばらく攪拌した。水層を酢酸エチルで抽出し、有機層を合わせて2 N塩酸水溶液と飽和食塩水で洗浄後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去することで、粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)-4-メチルチオフェン-3-イル)メタンスルホンアミド（2.89 g）を得た。
（３）上記（２）で合成した粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)-4-メチルチオフェン-3-イル)メタンスルホンアミド（1.45 g）をトルエン（40 ml）に溶解し、ｐ－トルエンスルホン酸一水和物（760 mg）と2－ピペリドン（793 mg）とを加えた。反応溶液を加熱し、Dean-Stark蒸留装置を用いて共沸脱水しながら２時間攪拌した。室温まで冷却後、酢酸エチルで希釈し、飽和食塩水で洗浄した。硫酸ナトリウムで乾燥した後、溶媒を減圧下で留去し、得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～１：１）で精製し、粗製の目的物（785 mg、化合物No.13-1）を薄い黄色固体として得た。 Synthesis example 3
Synthesis of 1,1,1-trifluoro-N- (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 13-1) (1) Under a nitrogen atmosphere, a solution of methyl 3-amino-4-methylthiophene-2-carboxylate (5.41 g), triethylamine (5.26 ml) and chloroform (200 ml) was cooled to −4 ° C. to obtain trifluoromethanesulfone. A mixed solution of acid anhydride (10.7 g) and chloroform (20 ml) was added dropwise over 25 minutes. The mixture was further stirred for 1 hour while cooling with ice, and water was added to stop the reaction. The aqueous layer was extracted with chloroform. The organic layers were combined and washed twice with 2N aqueous sodium hydroxide solution (100 ml). The aqueous alkaline solution was separated and stirred at reflux for 20 minutes. After cooling to room temperature, it was acidified with concentrated hydrochloric acid. The suspension was stirred while cooling with ice, and the resulting solid was filtered, washed with water, and then dried under reduced pressure to give 4-methyl-3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid. The acid was obtained as a pale pink solid (3.09 g). (Melting point 164-166 ° C) 1 H-NMR (500 MHz, CDCl 3 , δppm): 2.34 (s, 3H), 7.29 (s, 1H), 8.45 (br s, 1H).
(2) 4-Methyl-3- (trifluoromethylsulfonamido) thiophene-2-carboxylic acid (2.82 g) obtained in (1) above was dissolved in THF (50 ml), and iced in advance under a nitrogen atmosphere. The solution was added dropwise to a cooled suspension of lithium aluminum hydride (1.15 g) and THF (50 ml) over 20 minutes. The mixture was stirred for 1 hour under reflux, and after cooling, water was added under ice cooling to stop the reaction. Ethyl acetate and 2N aqueous hydrochloric acid solution were added, and the mixture was stirred for a while. The aqueous layer was extracted with ethyl acetate, and the organic layers were combined, washed with 2N aqueous hydrochloric acid and saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give crude 1,1,1 -Trifluoro-N- (2- (hydroxymethyl) -4-methylthiophen-3-yl) methanesulfonamide (2.89 g) was obtained.
(3) Crude 1,1,1-trifluoro-N- (2- (hydroxymethyl) -4-methylthiophen-3-yl) methanesulfonamide (1.45 g) synthesized in (2) above was added to toluene (1.45 g). 40 ml), p-toluenesulfonic acid monohydrate (760 mg) and 2-piperidone (793 mg) were added. The reaction solution was heated and stirred for 2 hours with azeotropic dehydration using a Dean-Stark distillation apparatus. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with saturated brine. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 1: 1) to obtain a crude target product (785 mg, Compound No. 13-1) was obtained as a pale yellow solid.

　・合成例４
エチル (4-メチル-2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)((トリフルオロメチル)スルホニル)カーバメート（化合物No.13-3）の合成
　1,1,1-トリフルオロ-N-(4-メチル-2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（785 mg）をトルエン（10 ml）に溶解させ、ピリジン（0.36 ml）とクロロギ酸エチル（0.42 ml）とを加えて、室温で２時間攪拌した。2 N塩酸水溶液を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～１：１）で精製し、目的物（760 mg、化合物No.13-3）を薄い褐色油状物質として得た。 Synthesis example 4
Synthesis of ethyl (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 13-3) 1,1, 1-trifluoro-N- (4-methyl-2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (785 mg) was dissolved in toluene (10 ml), Pyridine (0.36 ml) and ethyl chloroformate (0.42 ml) were added, and the mixture was stirred at room temperature for 2 hours. After 2 N hydrochloric acid aqueous solution was added to stop the reaction, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 1: 1) to obtain the desired product (760 mg, compound No. 13-3) as a pale brown oily substance.

　・合成例５
1,1,1-トリフルオロ-N-(2-((2-チオキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（化合物No.1-46）の合成
　1,1,1-トリフルオロ-N-(2-((2-オキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（321 mg）をトルエン（10 ml）に溶解させ、そこにローソン試薬（469 mg）を加えて、還流下で5時間攪拌した。室温まで冷却し、カラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～０：１０）で精製し、目的物（243 mg、化合物No.1-46）を淡黄色固体として得た。 Synthesis example 5
Synthesis of 1,1,1-trifluoro-N- (2-((2-thioxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 1-46) 1,1 , 1-Trifluoro-N- (2-((2-oxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (321 mg) dissolved in toluene (10 ml), and then Lawson Reagent (469 mg) was added and stirred under reflux for 5 hours. The mixture was cooled to room temperature and purified by column chromatography (heptane: ethyl acetate = 9: 1 to 0:10) to obtain the desired product (243 mg, compound No. 1-46) as a pale yellow solid.

　・合成例６
エチル(2-((2-チオキソピペリジン-1-イル)メチル)チオフェン-3-イル)((トリフルオロメチル)スルホニル)カーバメート（化合物No.1-48）の合成
　1,1,1-トリフルオロ-N-(2-((2-チオキソピペリジン-1-イル)メチル)チオフェン-3-イル)メタンスルホンアミド（163 mg）をトルエン（3 ml）に溶解させ、ピリジン（0.10 ml）とクロロギ酸エチル（0.10 ml）とを加えて、室温で２時間攪拌した。2 N塩酸水溶液を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝９：１～６：４）で精製し、目的物（191 mg、化合物No.1-48）を淡黄色固体として得た。 Synthesis example 6
Synthesis of ethyl (2-((2-thioxopiperidin-1-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 1-48) 1,1,1-Tri Fluoro-N- (2-((2-thioxopiperidin-1-yl) methyl) thiophen-3-yl) methanesulfonamide (163 mg) was dissolved in toluene (3 ml) and pyridine (0.10 ml) was dissolved. Ethyl chloroformate (0.10 ml) was added and stirred at room temperature for 2 hours. After 2 N hydrochloric acid aqueous solution was added to stop the reaction, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 9: 1 to 6: 4) to obtain the desired product (191 mg, compound No. 1-48) as a pale yellow solid.

　・合成例７
1,1,1-トリフルオロ-N-(2-((3-オキソモルホリノ)メチル)チオフェン-3-イル)メタンスルホンアミド（化合物No.6-1）の合成
（１）窒素雰囲気下、水素化ナトリウム（60 wt%、1.2 g）及びジオキサン（25 ml）の溶液を0℃に冷却し、エタノールアミン（1.5 ml）を加え室温で30分攪拌した。反応液を0℃に冷却し、クロロ酢酸エチル（2.7 ml）を加え室温で30分攪拌した後、加熱還流下でさらに40分攪拌した。反応液を冷却した後、ろ過して固体を除去した。ろ液を減圧下で濃縮し、得られた残渣をカラムクロマトグラフィー（酢酸エチル：メタノール＝19：1）で精製し、モルホリン-3-オン（500 mg）を無色固体として得た。
1H-NMR (500 MHz, CDCl3, δppm): 3.43-3.45 (m, 2H), 3.84 (t, J=5.0 Hz, 2H), 4.18 (s, 2H).
（２）窒素雰囲気下、3-アミノ-2-チオフェンカルボン酸メチル（3.0 g）、N,N-ジイソプロピルエチルアミン（10.0 ml）及びアセトニトリル（95 ml）の溶液を－30℃に冷却し、トリフルオロメタンスルホン酸無水物（9.6 ml）を15分かけて滴下した。温度を－30℃～20℃の間で維持しながら、さらに75分攪拌した。水を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝3：1）で精製し、メチル3-(1,1,1-トリフルオロ-N-((トリフルオロメチル)スルホニル)メチルスルホンアミド)チオフェン-2-カルボキシレート（7.0 g）を黄色固体として得た。
1H-NMR (500 MHz, CDCl3, δppm): 3.95 (s, 3H), 7.13 (d, J=6.0 Hz, 1H), 7.60 (d, J=6.0 Hz, 1H).
（３）上記（２）で合成した メチル 3-(1,1,1-トリフルオロ-N-((トリフルオロメチル)スルホニル)メチルスルホンアミド)チオフェン-2-カルボキシレート（4.0 g）をTHF（47 ml）に溶解させ、窒素雰囲気下、0℃にて、水素化ジイソブチルアルミニウム（1 Mトルエン溶液、23.7 ml）を15分かけて滴下した。室温に昇温してから14.5時間攪拌した後、0℃で反応液に、2 N塩酸を加え室温で３０分間攪拌した。反応液に水を加えて水層を酢酸エチルで抽出し、有機層を合わせて飽和食塩水で洗浄後、無水硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝7：1～2：1）で精製し、1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)-N-((トリフルオロメチル)スルホニル)メタンスルホンアミド（2.2 g）を褐色油状物質として得た。
1H-NMR (500 MHz, CDCl3, δppm): 4.82 (d,J=5.0 Hz, 2H), 6.96 (d,J=5.5 Hz, 1H), 7.38 (d,J=5.5 Hz, 1H).
（４）上記（３）で合成した1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)-N-((トリフルオロメチル)スルホニル)メタンスルホンアミド（800 mg）をエタノール（16 ml）に溶解し、0℃で、水酸化ナトリウム（244 mg）の水溶液（4 ml）を加え0℃で1時間攪拌した。反応溶液に水と2 N塩酸を加え反応液を酸性とした後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、溶媒を減圧下で留去し、粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)メタンスルホンアミド（530 mg）を薄い褐色油状物質として得た。
（５）上記（４）で合成した粗製の1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)メタンスルホンアミド（530 mg）をトルエン（10 ml）に溶解させ、p-トルエンスルホン酸一水和物（40 mg）と上記（１）で合成したモルホリン-3-オン（410 mg）とを加えて、加熱還流下で1時間攪拌した。水を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝1：2）で精製し、目的物（260 mg、化合物No.6-1）を無色固体として得た。 Synthesis example 7
Synthesis of 1,1,1-trifluoro-N- (2-((3-oxomorpholino) methyl) thiophen-3-yl) methanesulfonamide (Compound No. 6-1) (1) Hydrogen in a nitrogen atmosphere A solution of sodium halide (60 wt%, 1.2 g) and dioxane (25 ml) was cooled to 0 ° C., ethanolamine (1.5 ml) was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was cooled to 0 ° C., ethyl chloroacetate (2.7 ml) was added, and the mixture was stirred at room temperature for 30 min. After cooling the reaction solution, the solid was removed by filtration. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (ethyl acetate: methanol = 19: 1) to obtain morpholin-3-one (500 mg) as a colorless solid.
1 H-NMR (500 MHz, CDCl 3 , δppm): 3.43-3.45 (m, 2H), 3.84 (t, J = 5.0 Hz, 2H), 4.18 (s, 2H).
(2) Under a nitrogen atmosphere, a solution of methyl 3-amino-2-thiophenecarboxylate (3.0 g), N, N-diisopropylethylamine (10.0 ml) and acetonitrile (95 ml) was cooled to −30 ° C. to obtain trifluoromethane. Sulfonic anhydride (9.6 ml) was added dropwise over 15 minutes. The mixture was further stirred for 75 minutes while maintaining the temperature between -30 ° C and 20 ° C. Water was added to stop the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (heptane: ethyl acetate = 3: 1) and methyl 3- (1,1,1-trifluoro-N-((trifluoromethyl) sulfonyl) methylsulfonamido) thiophen-2- Carboxylate (7.0 g) was obtained as a yellow solid.
1 H-NMR (500 MHz, CDCl 3 , δppm): 3.95 (s, 3H), 7.13 (d, J = 6.0 Hz, 1H), 7.60 (d, J = 6.0 Hz, 1H).
(3) Methyl 3- (1,1,1-trifluoro-N-((trifluoromethyl) sulfonyl) methylsulfonamido) thiophene-2-carboxylate (4.0 g) synthesized in (2) above was converted to THF ( 47 ml), and diisobutylaluminum hydride (1 M toluene solution, 23.7 ml) was added dropwise over 15 minutes at 0 ° C. in a nitrogen atmosphere. After warming to room temperature and stirring for 14.5 hours, 2 N hydrochloric acid was added to the reaction solution at 0 ° C., and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 7: 1 to 2: 1) and 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophen-3-yl) -N-((trifluoromethyl) sulfonyl) methanesulfonamide (2.2 g) was obtained as a brown oil.
1 H-NMR (500 MHz, CDCl 3 , δppm): 4.82 (d, J = 5.0 Hz, 2H), 6.96 (d, J = 5.5 Hz, 1H), 7.38 (d, J = 5.5 Hz, 1H).
(4) 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophen-3-yl) -N-((trifluoromethyl) sulfonyl) methanesulfonamide (800) synthesized in (3) above mg) was dissolved in ethanol (16 ml), an aqueous solution (4 ml) of sodium hydroxide (244 mg) was added at 0 ° C., and the mixture was stirred at 0 ° C. for 1 hour. Water and 2N hydrochloric acid were added to the reaction solution to acidify the reaction solution, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain crude 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophene. -3-yl) methanesulfonamide (530 mg) was obtained as a light brown oil.
(5) Crude 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophen-3-yl) methanesulfonamide (530 mg) synthesized in (4) above was added to toluene (10 ml). After dissolving, p-toluenesulfonic acid monohydrate (40 mg) and morpholin-3-one synthesized in (1) above (410 mg) were added, and the mixture was stirred for 1 hour under heating to reflux. Water was added to stop the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 1: 2) to obtain the desired product (260 mg, compound No. 6-1) as a colorless solid.

　・合成例８
エチル (2-((3-オキソモルホリノ)メチル)チオフェン-3-イル)((トリフルオロメチル)スルホニル)カーバメート（化合物No.6-3）の合成
　1,1,1-トリフルオロ-N-(2-((3-オキソモルホリノ)メチル)チオフェン-3-イル)メタンスルホンアミド（150 mg）をトルエン（4.4 ml）に溶解させ、ピリジン（0.06 ml）とクロロギ酸エチル（0.07 ml）とを加えて、室温で15時間攪拌した。水を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝１：１）で精製し、目的物（120 mg、化合物No.6-3）を薄い褐色油状物質として得た。 Synthesis example 8
Synthesis of ethyl (2-((3-oxomorpholino) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 6-3) 1,1,1-trifluoro-N- ( 2-((3-oxomorpholino) methyl) thiophen-3-yl) methanesulfonamide (150 mg) is dissolved in toluene (4.4 ml) and pyridine (0.06 ml) and ethyl chloroformate (0.07 ml) are added. And stirred at room temperature for 15 hours. Water was added to stop the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 1: 1) to obtain the desired product (120 mg, compound No. 6-3) as a pale brown oily substance.

　・合成例９
N-(2-((6,6-ジメチル-2-オキソ-1,3-オキサジナン-3-イル)メチル)チオフェン-3-イル)-1,1,1-トリフルオロメタンスルホンアミド（化合物No.2-33）の合成
（１）3-ヒドロキシ-3-メチルブチロニトリル（10 ml）をTHF（50 ml）に溶解させ、窒素雰囲気下、予め氷冷した水素化リチウムアルミニウム（8.0 g）とTHF（150 ml）の懸濁液に２０分かけて滴下した。還流下で４時間攪拌し、冷却後氷冷下で硫酸ナトリウム10水和物とフッ化カリウムとを加えた。室温下で３０分攪拌した後、セライトを用いてろ過を行った。ろ液を硫酸ナトリウムで乾燥し、溶媒を減圧下で留去することで、粗製の3-アミノ-1,1-ジメチル-1-プロパノール（12.7 g）を薄い褐色油状物質として得た。
（２）上記（１）で得られた3-アミノ-1,1-ジメチル-1-プロパノール（6.0 g）をメタノール（60 ml）に溶解させ、窒素雰囲気下、4-メトキシベンズアルデヒド（12.2 ml）と触媒量の酢酸とを加えた。還流下で１時間攪拌し、冷却後氷冷下で水素化ホウ素ナトリウム（4.38 g）を加え、室温で２時間攪拌した。3 N塩酸水溶液を加え１０分間攪拌した後、酢酸エチルを加え抽出し、さらに水層を酢酸エチルで洗浄した。水層に6 N水酸化ナトリウム水溶液を加え塩基性にした後、酢酸エチルで抽出した。有機層を硫酸ナトリウムで乾燥し、溶媒を減圧下で留去することで、3-(4-メトキシベンジルアミノ)-1,1-ジメチル-1-プロパノール（6.67 g）を褐色油状物質として得た。
1H-NMR (500 MHz, CDCl3, δppm): 1.19 (s, 6H), 1.60 (t, J=5.5 Hz, 2H), 2.90 (t, J=5.5 Hz, 2H), 3.70 (s, 2H), 3.78 (s, 3H), 6.84 (d, J=8.5 Hz, 2H), 7.20 (d, J=8.5Hz, 2H).
（３）上記（２）で得られた3-(4-メトキシベンジルアミノ)-1,1-ジメチル-1-プロパノール（6.67 g）をトルエン（100 ml）に溶解させ、窒素雰囲気下、予め氷冷した水素化ナトリウム（60 wt%、1.55 g）とトルエン（200 ml）の懸濁液に１０分かけて滴下した。室温で３０分攪拌した後、炭酸ジエチル（5.44 ml）を滴下し、還流下で１２時間攪拌した。室温で飽和塩化アンモニア水を加えて反応を停止させ、水層を酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、硫酸ナトリウムで乾燥させ溶媒を減圧下で留去し、得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝3：7～0：10）で精製し、3-(4-メトキシベンジル)-6,6-ジメチル-1,3-オキサジナン-2-オン（4.21 g）を薄い褐色固体として得た。
1H-NMR (500 MHz, CDCl3, δppm): 1.36 (s, 6H), 1.82 (t, J=6.5 Hz, 2H), 3.17 (t, J=6.5 Hz, 2H), 3.80 (s, 3H), 4.51 (s, 2H), 6.86 (d, J=9.0 Hz, 2H), 7.23 (d, J=9.0Hz, 2H).
（４）上記（３）で得られた3-(4-メトキシベンジル)-6,6-ジメチル-1,3-オキサジナン-2-オン（4.21 g）をアセトニトリル（168 ml）に溶解させ、室温で硝酸アンモニウムセリウム（IV）（27.77 g）と水（84 ml）とを加えて１２時間攪拌した。溶媒を減圧下で留去後、ろ過を行い、固形物を除いた。得られたろ液を硫酸ナトリウムで乾燥させ溶媒を減圧下で留去し、得られた残渣をカラムクロマトグラフィー（エタノール：酢酸エチル＝0：10～1：9）で精製し、6,6-ジメチル-1,3-オキサジナン-2-オン（2.10 g）を薄い褐色油状物質として得た。
1H-NMR (500 MHz, CDCl3, δppm): 1.44 (s, 6H), 1.94 (br s, 2H), 3.56 (br s, 2H).
（５）1,1,1-トリフルオロ-N-(2-(ヒドロキシメチル)チオフェン-3-イル)メタンスルホンアミド（0.79 g）をトルエン（55 ml）に溶解し、ｐ－トルエンスルホン酸一水和物（0.63 g）と上記（４）で得られた6,6-ジメチル-1,3-オキサジナン-2-オン（0.43 g）とを加えた。反応溶液を加熱し、Dean-Stark蒸留装置を用いて共沸脱水しながら２時間攪拌した。室温まで冷却後、酢酸エチルで希釈し、飽和食塩水で洗浄した。硫酸ナトリウムで乾燥した後、溶媒を減圧下で留去し、得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝3：7～0：10）で精製し、粗製の目的物（0.14 g、化合物No.2-33）を薄い褐色油状物質として得た。 Synthesis example 9
N- (2-((6,6-dimethyl-2-oxo-1,3-oxazinan-3-yl) methyl) thiophen-3-yl) -1,1,1-trifluoromethanesulfonamide (Compound No. Synthesis of 2-33) (1) 3-Hydroxy-3-methylbutyronitrile (10 ml) was dissolved in THF (50 ml) and pre-ice-cooled lithium aluminum hydride (8.0 g) in a nitrogen atmosphere. It was added dropwise to a suspension of THF (150 ml) over 20 minutes. The mixture was stirred for 4 hours under reflux, and after cooling, sodium sulfate decahydrate and potassium fluoride were added under ice cooling. After stirring for 30 minutes at room temperature, filtration was performed using Celite. The filtrate was dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain crude 3-amino-1,1-dimethyl-1-propanol (12.7 g) as a light brown oily substance.
(2) 3-Amino-1,1-dimethyl-1-propanol (6.0 g) obtained in (1) above was dissolved in methanol (60 ml), and 4-methoxybenzaldehyde (12.2 ml) was added under a nitrogen atmosphere. And a catalytic amount of acetic acid were added. The mixture was stirred for 1 hour under reflux, and after cooling, sodium borohydride (4.38 g) was added under ice cooling, followed by stirring at room temperature for 2 hours. A 3N aqueous hydrochloric acid solution was added and the mixture was stirred for 10 minutes, followed by extraction with ethyl acetate, and the aqueous layer was further washed with ethyl acetate. The aqueous layer was made basic by adding 6N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 3- (4-methoxybenzylamino) -1,1-dimethyl-1-propanol (6.67 g) as a brown oily substance. .
1 H-NMR (500 MHz, CDCl 3 , δppm): 1.19 (s, 6H), 1.60 (t, J = 5.5 Hz, 2H), 2.90 (t, J = 5.5 Hz, 2H), 3.70 (s, 2H ), 3.78 (s, 3H), 6.84 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.5Hz, 2H).
(3) 3- (4-Methoxybenzylamino) -1,1-dimethyl-1-propanol (6.67 g) obtained in (2) above is dissolved in toluene (100 ml), and iced in advance under a nitrogen atmosphere. The mixture was added dropwise to a cooled suspension of sodium hydride (60 wt%, 1.55 g) and toluene (200 ml) over 10 minutes. After stirring at room temperature for 30 minutes, diethyl carbonate (5.44 ml) was added dropwise, and the mixture was stirred under reflux for 12 hours. Saturated aqueous ammonia chloride was added at room temperature to stop the reaction, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 3: 7-0: 10), 3- (4-Methoxybenzyl) -6,6-dimethyl-1,3-oxazinan-2-one (4.21 g) was obtained as a light brown solid.
1 H-NMR (500 MHz, CDCl 3 , δppm): 1.36 (s, 6H), 1.82 (t, J = 6.5 Hz, 2H), 3.17 (t, J = 6.5 Hz, 2H), 3.80 (s, 3H ), 4.51 (s, 2H), 6.86 (d, J = 9.0 Hz, 2H), 7.23 (d, J = 9.0Hz, 2H).
(4) 3- (4-Methoxybenzyl) -6,6-dimethyl-1,3-oxazinan-2-one (4.21 g) obtained in (3) above was dissolved in acetonitrile (168 ml) Then, ammonium cerium (IV) nitrate (27.77 g) and water (84 ml) were added and stirred for 12 hours. The solvent was distilled off under reduced pressure, followed by filtration to remove solids. The obtained filtrate was dried over sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (ethanol: ethyl acetate = 0: 10-1: 9) to give 6,6-dimethyl -1,3-oxazinan-2-one (2.10 g) was obtained as a light brown oil.
1 H-NMR (500 MHz, CDCl 3 , δppm): 1.44 (s, 6H), 1.94 (br s, 2H), 3.56 (br s, 2H).
(5) Dissolve 1,1,1-trifluoro-N- (2- (hydroxymethyl) thiophen-3-yl) methanesulfonamide (0.79 g) in toluene (55 ml). Hydrate (0.63 g) and 6,6-dimethyl-1,3-oxazinan-2-one (0.43 g) obtained in (4) above were added. The reaction solution was heated and stirred for 2 hours with azeotropic dehydration using a Dean-Stark distillation apparatus. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with saturated brine. After drying with sodium sulfate, the solvent was distilled off under reduced pressure, and the resulting residue was purified by column chromatography (heptane: ethyl acetate = 3: 7 to 0:10) to obtain a crude target product (0.14 g, Compound No. 2-33) was obtained as a light brown oil.

　・合成例１０
エチル(2-((6,6-ジメチル-2-オキソ-1,3-オキサジナン-3-イル)メチル)チオフェン-3-イル)((トリフルオロメチル)スルホニル)カーバメート（化合物No.2-35）の合成
　N-(2-((6,6-ジメチル-2-オキソ-1,3-オキサジナン-3-イル)メチル)チオフェン-3-イル)-1,1,1-トリフルオロメタンスルホンアミド（0.14 g）をトルエン（5.0 ml）に溶解させ、ピリジン（59.3 mg）とクロロギ酸エチル（81.4 mg）とを加えて、室温で２時間攪拌した。2 N塩酸水溶液を加え反応を停止した後、水層を酢酸エチルで抽出した。有機層を合わせて飽和食塩水で洗浄した後、硫酸ナトリウムで乾燥し、溶媒を減圧下で留去した。得られた残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝7：3～3：7）で精製し、目的物（79 mg、化合物No.2-35）を薄い褐色固体として得た。 Synthesis example 10
Ethyl (2-((6,6-dimethyl-2-oxo-1,3-oxazinan-3-yl) methyl) thiophen-3-yl) ((trifluoromethyl) sulfonyl) carbamate (Compound No. 2-35 ) N- (2-((6,6-Dimethyl-2-oxo-1,3-oxazinan-3-yl) methyl) thiophen-3-yl) -1,1,1-trifluoromethanesulfonamide ( 0.14 g) was dissolved in toluene (5.0 ml), pyridine (59.3 mg) and ethyl chloroformate (81.4 mg) were added, and the mixture was stirred at room temperature for 2 hours. After 2 N hydrochloric acid aqueous solution was added to stop the reaction, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (heptane: ethyl acetate = 7: 3 to 3: 7) to obtain the desired product (79 mg, compound No. 2-35) as a light brown solid.

　次に、本発明化合物の代表例を第１表から第１３表に挙げる。これらの化合物は、前記合成例或いは前記した種々の製造方法に基づいて合成することができる。第１表から第１３表中、物性欄に記載の数値は融点（℃）を表し、NMRと記載されている化合物はそれらの1H-NMRスペクトルデータ及び測定に使用した溶媒を第１４表に挙げる。尚、第１表から第１４表中、No.は化合物No.を示す。また、表中、Meはメチル基を、Etはエチル基を、n-Prはノルマルプロピル基を、i-Prはイソプロピル基を、c-Prはシクロプロピル基を、n-Buはノルマルブチル基を、s-Buはセカンダリーブチル基を、i-Buはイソブチル基を、t-Buはターシャリーブチル基を、c-Hexはシクロヘキシル基を、c-Buはシクロブチル基を、Phはフェニル基を、C=Oはカルボニル基を各々示す。また、3-CF3Phは3位にCF3が置換したフェニル基を表し、他の同様の記載もこれに準じる。 Next, typical examples of the compounds of the present invention are listed in Tables 1 to 13. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Tables 1 to 13, the numerical values described in the physical properties column represent melting points (° C.), and for compounds described as NMR, the 1 H-NMR spectrum data and the solvent used for the measurement are shown in Table 14. I will give you. In Tables 1 to 14, No. indicates the compound number. In the table, Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, c-Pr is a cyclopropyl group, and n-Bu is a normal butyl group. S-Bu is a secondary butyl group, i-Bu is an isobutyl group, t-Bu is a tertiary butyl group, c-Hex is a cyclohexyl group, c-Bu is a cyclobutyl group, and Ph is a phenyl group. And C = O each represents a carbonyl group. In addition, 3-CF 3 Ph represents a phenyl group substituted with CF 3 at the 3-position, and other similar descriptions are based on this.

　表中E-1からE-12は各々下記の構造を表す。 In the table, E-1 to E-12 each represent the following structure.

Figure JPOXMLDOC01-appb-C000020
Figure JPOXMLDOC01-appb-C000020

Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000021

Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000022

Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023

Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024

Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025

Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026

Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027

Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028

Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029

Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030

Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031

Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032

Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033

Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034

Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035

Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036

Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037

Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039

Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040

Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041

Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042

Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000043

Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000044

Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000045

Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000046

Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047

Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000048

Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049

Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050

Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000051

Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052

Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053

Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054

Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055

Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056

Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057

Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000058

Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059

Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060

Figure JPOXMLDOC01-appb-T000061
Figure JPOXMLDOC01-appb-T000061

Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062

Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000063

Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064

Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065

Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000066

Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000067

Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000068

Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000069

Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000070

Figure JPOXMLDOC01-appb-T000071
Figure JPOXMLDOC01-appb-T000071

Figure JPOXMLDOC01-appb-T000072
Figure JPOXMLDOC01-appb-T000072

Figure JPOXMLDOC01-appb-T000073
Figure JPOXMLDOC01-appb-T000073

Figure JPOXMLDOC01-appb-T000074
Figure JPOXMLDOC01-appb-T000074

Figure JPOXMLDOC01-appb-T000075
Figure JPOXMLDOC01-appb-T000075

Figure JPOXMLDOC01-appb-T000076
Figure JPOXMLDOC01-appb-T000076

Figure JPOXMLDOC01-appb-T000077
Figure JPOXMLDOC01-appb-T000077

Figure JPOXMLDOC01-appb-T000078
Figure JPOXMLDOC01-appb-T000078

Figure JPOXMLDOC01-appb-T000079
Figure JPOXMLDOC01-appb-T000079

Figure JPOXMLDOC01-appb-T000080
Figure JPOXMLDOC01-appb-T000080

Figure JPOXMLDOC01-appb-T000081
Figure JPOXMLDOC01-appb-T000081

Figure JPOXMLDOC01-appb-T000082
Figure JPOXMLDOC01-appb-T000082

Figure JPOXMLDOC01-appb-T000083
Figure JPOXMLDOC01-appb-T000083

Figure JPOXMLDOC01-appb-T000084
Figure JPOXMLDOC01-appb-T000084

Figure JPOXMLDOC01-appb-T000085
Figure JPOXMLDOC01-appb-T000085

Figure JPOXMLDOC01-appb-T000086
Figure JPOXMLDOC01-appb-T000086

Figure JPOXMLDOC01-appb-T000087
Figure JPOXMLDOC01-appb-T000087

Figure JPOXMLDOC01-appb-T000088
Figure JPOXMLDOC01-appb-T000088

Figure JPOXMLDOC01-appb-T000089
Figure JPOXMLDOC01-appb-T000089

Figure JPOXMLDOC01-appb-T000090
Figure JPOXMLDOC01-appb-T000090

Figure JPOXMLDOC01-appb-T000091
Figure JPOXMLDOC01-appb-T000091

Figure JPOXMLDOC01-appb-T000092
Figure JPOXMLDOC01-appb-T000092

Figure JPOXMLDOC01-appb-T000093
Figure JPOXMLDOC01-appb-T000093

Figure JPOXMLDOC01-appb-T000094
Figure JPOXMLDOC01-appb-T000094

Figure JPOXMLDOC01-appb-T000095
Figure JPOXMLDOC01-appb-T000095

Figure JPOXMLDOC01-appb-T000096
Figure JPOXMLDOC01-appb-T000096

Figure JPOXMLDOC01-appb-T000097
Figure JPOXMLDOC01-appb-T000097

Figure JPOXMLDOC01-appb-T000098
Figure JPOXMLDOC01-appb-T000098

Figure JPOXMLDOC01-appb-T000099
Figure JPOXMLDOC01-appb-T000099

Figure JPOXMLDOC01-appb-T000100
Figure JPOXMLDOC01-appb-T000100

Figure JPOXMLDOC01-appb-T000101
Figure JPOXMLDOC01-appb-T000101

Figure JPOXMLDOC01-appb-T000102
Figure JPOXMLDOC01-appb-T000102

Figure JPOXMLDOC01-appb-T000103
Figure JPOXMLDOC01-appb-T000103

Figure JPOXMLDOC01-appb-T000104
Figure JPOXMLDOC01-appb-T000104

Figure JPOXMLDOC01-appb-T000105
Figure JPOXMLDOC01-appb-T000105

Figure JPOXMLDOC01-appb-T000106
Figure JPOXMLDOC01-appb-T000106

Figure JPOXMLDOC01-appb-T000107
Figure JPOXMLDOC01-appb-T000107

Figure JPOXMLDOC01-appb-T000108
Figure JPOXMLDOC01-appb-T000108

Figure JPOXMLDOC01-appb-T000109
Figure JPOXMLDOC01-appb-T000109

Figure JPOXMLDOC01-appb-T000110
Figure JPOXMLDOC01-appb-T000110

Figure JPOXMLDOC01-appb-T000111
Figure JPOXMLDOC01-appb-T000111

Figure JPOXMLDOC01-appb-T000112
Figure JPOXMLDOC01-appb-T000112

Figure JPOXMLDOC01-appb-T000113
Figure JPOXMLDOC01-appb-T000113

Figure JPOXMLDOC01-appb-T000114
Figure JPOXMLDOC01-appb-T000114

Figure JPOXMLDOC01-appb-T000115
Figure JPOXMLDOC01-appb-T000115

Figure JPOXMLDOC01-appb-T000116
Figure JPOXMLDOC01-appb-T000116

Figure JPOXMLDOC01-appb-T000117
Figure JPOXMLDOC01-appb-T000117

Figure JPOXMLDOC01-appb-T000118
Figure JPOXMLDOC01-appb-T000118

Figure JPOXMLDOC01-appb-T000119
Figure JPOXMLDOC01-appb-T000119

Figure JPOXMLDOC01-appb-T000120
Figure JPOXMLDOC01-appb-T000120

Figure JPOXMLDOC01-appb-T000121
Figure JPOXMLDOC01-appb-T000121

Figure JPOXMLDOC01-appb-T000122
Figure JPOXMLDOC01-appb-T000122

Figure JPOXMLDOC01-appb-T000123
Figure JPOXMLDOC01-appb-T000123

Figure JPOXMLDOC01-appb-T000124
Figure JPOXMLDOC01-appb-T000124

Figure JPOXMLDOC01-appb-T000125
Figure JPOXMLDOC01-appb-T000125

Figure JPOXMLDOC01-appb-T000126
Figure JPOXMLDOC01-appb-T000126

　・試験例１
　1／170,000ヘクタールポットに畑作土壌をつめ、各種植物の種子を播種した。その後、植物が一定の葉令（（１）イヌビエ(barnyardgrass (Echinochloa crus-galli L.))；0.5～3.0葉期、（２）メヒシバ(crabgrass (Digitaria sanguinalis L.))；0.5～3.0葉期、
（３）エノコログサ(green foxtail (Setariaviridis L.))；1.0～3.5葉期、（４）アオゲイトウ(redroot pigweed (Amaranthusretroflexus L.))；0.2～2.5葉期、（５）アメリカキンゴジカ(prickly sida (Sida spinosa L.))；子葉～2.0葉期、（６）イチビ(velvetleaf (Abutilon theophrastiMEDIC.))；0.2～2.0葉期、（７）イネ(rice (Oryza sativa L.))；0.5～2.5葉期、（８）トウモロコシ(corn (Zea maysL.))；2.0～3.5葉期、（９）コムギ(wheat (Triticum spp.))；2.0～5.0葉期、（10）ワタ(cotton (Gossypium spp.))；初生葉～0.5葉期、（11）ダイズ(soybean (Glycine maxMerr.))；初生葉～0.5葉期）に達したとき、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤を所定の有効成分量となるように秤量し、1ヘクタール当り500リットル相当の水（農業用展着剤（クサリノー：日本農薬株式会社製）を0.1容量％含有）に希釈した。調製した散布液を小型スプレーで茎葉処理した。 Test example 1
A field crop soil was packed in a 1 / 170,000 hectare pot and seeds of various plants were sown. After that, the plant had a certain leaf age ((1) barnyardgrass (Echinochloa crus-galli L.); 0.5-3.0 leaf stage, (2) crabgrass (Digitaria sanguinalis L.)); 0.5-3.0 leaf stage ,
(3) Green foxtail (Setariaviridis L.); 1.0-3.5 leaves, (4) Red root pigweed (Amaranthusretroflexus L.); 0.2-2.5 leaves, (5) American prickly sida (prickly sida ( Sida spinosa L.)); cotyledon-2.0 leaf stage, (6) velvetleaf (Abutilon theophrastiMEDIC.); 0.2-2.0 leaf stage, (7) rice (rice (Oryza sativa L.)); 0.5-2.5 leaf (8) Corn (Zea maysL.); 2.0-3.5 leaf stage, (9) Wheat (Triticum spp.); 2.0-5.0 leaf stage, (10) Cotton (Gossypium spp. )); Primary leaves to 0.5 leaf stage, (11) soybean (Glycine maxMerr.); Primary leaves to 0.5 leaf stage), the compound according to the present invention was prepared according to the usual formulation method Wettable powder or emulsion is weighed to the prescribed active ingredient amount and diluted in water equivalent to 500 liters per hectare (agricultural spreading agent (xalino: manufactured by Nippon Agricultural Chemicals) containing 0.1% by volume) It was. The prepared spray was treated with a small spray.

　薬剤処理後、13～21日目に各種植物の生育状態を肉眼観察し、0（無処理区と同等）～100（完全枯殺）の生育抑制率（％）で除草効果を評価し、第１５表の結果を得た。 After chemical treatment, on the 13th to 21st days, the state of growth of various plants was observed with the naked eye, and the herbicidal effect was evaluated with a growth inhibition rate (%) of 0 (equivalent to the untreated area) to 100 (completely killed). The results shown in Table 15 were obtained.

Figure JPOXMLDOC01-appb-T000127
Figure JPOXMLDOC01-appb-T000127

Figure JPOXMLDOC01-appb-T000128
Figure JPOXMLDOC01-appb-T000128

Figure JPOXMLDOC01-appb-T000129
Figure JPOXMLDOC01-appb-T000129

　・試験例２
　1／170,000ヘクタールポットもしくは1／300,000ヘクタールポットに畑作土壌をつめ、各種植物（イヌビエ(barnyardgrass(Echinochloacrus-galli L.))、メヒシバ(crabgrass (Digitariasanguinalis L.))、エノコログサ(green foxtail (Setariaviridis L.))、アオゲイトウ(redroot pigweed (Amaranthusretroflexus L.))、アメリカキンゴジカ(prickly sida (Sidaspinosa L.))、イチビ(velvetleaf (Abutilon theophrastiMEDIC.))、イネ(rice (oryza sativa L.))、トウモロコシ(corn (Zea mays L.))、コムギ(wheat (Triticum spp.))、ワタ(cotton (Gossypiumspp.))、ダイズ(soybean (Glycine max Merr.))）の種子を播種した。播種翌日、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤を所定の有効成分量となるように秤量し、１ヘクタール当り500リットルもしくは1000リットル相当の水に希釈し、小型スプレーで土壌処理した。 Test example 2
Field crop soil is packed in 1 / 170,000 hectare pot or 1 / 300,000 hectare pot, and various plants (barnyardgrass (Echinochloacrus-galli L.)), barkyard (crabgrass (Digitariasanguinalis L.)), green foxtail (Setariaviridis L. )), Red root pigweed (Amaranthusretroflexus L.)), American deer (prickly sida (Sidaspinosa L.)), green velvetleaf (Abutilon theophrastiMEDIC.), Rice (rice (oryza sativa L.)), corn ( corn (Zea mays L.)), wheat (wheat (Triticum spp.)), cotton (cotton (Gossypiumspp.)), soybean (soybean (Glycine max Merr.))) were sown. On the day after sowing, a wettable powder or emulsion prepared according to the usual formulation method of the compound according to the present invention is weighed to a predetermined active ingredient amount, and diluted to 500 liters or 1000 liters of water per hectare. The soil was treated with a small spray.

　薬剤処理後、14～21日目に各種植物の生育状態を肉眼観察し、0（無処理区と同等）～100（完全枯殺）の生育抑制率（％）で除草効果を評価し、第１６表の結果を得た。 On the 14th to 21st days after chemical treatment, the growth state of various plants was visually observed, and the herbicidal effect was evaluated with a growth inhibition rate (%) of 0 (equivalent to the untreated area) to 100 (completely killed). The results of Table 16 were obtained.

Figure JPOXMLDOC01-appb-T000130
Figure JPOXMLDOC01-appb-T000130

Figure JPOXMLDOC01-appb-T000131
Figure JPOXMLDOC01-appb-T000131

Figure JPOXMLDOC01-appb-T000132
Figure JPOXMLDOC01-appb-T000132

Figure JPOXMLDOC01-appb-T000133
Figure JPOXMLDOC01-appb-T000133

　・試験例３
　1／1,000,000ヘクタールポットに水田土壌を詰め、タイヌビエ(barnyardgrass (Echinochloa oryzicola vasing.))及びホタルイ(Japanese bulrush (Scirpus juncoides))の種子を播種し、その上に軽く覆土した。その後、湛水深0.5～1ｃｍの状態で温室内に静置し、翌日にウリカワ(Japanese ribbon waparo (Sagittaria pygmaea))の塊茎を植え込んだ。その後、湛水深を3～4ｃｍに保ち、タイヌビエ及びホタルイが0.5葉期、ウリカワが初生葉期に達した時点で、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤の水希釈液を、所定の有効成分量になるようにピペットで均一に滴下処理した。また、1／1,000,000ヘクタールポットに水田土壌を詰め、代かきを行い、湛水深を3～4ｃｍとし、翌日に2葉期のイネ(rice (Oryza sativa L.))（品種：日本晴）を移植深3ｃｍに移植した。移植翌日に本発明に係る化合物を前述と同様に処理した。 Test example 3
Paddy soil was packed in a 1 / 1,000,000 hectare pot, seeds of barnyardgrass (Echinochloa oryzicola vasing.) And firefly (Japanese bulrush (Scirpus juncoides)) were sown and lightly soiled on top. After that, it was left in a greenhouse at a depth of 0.5 to 1 cm, and a tuber of Urikawa (Japanese ribbon waparo (Sagittaria pygmaea)) was planted the next day. Thereafter, the water depth was maintained at 3 to 4 cm, and when the Tainubier and Firefly reached the 0.5 leaf stage and Urikawa reached the primary leaf stage, the compound according to the present invention was prepared according to a conventional formulation method or a wettable powder or emulsion. The aqueous diluted solution was uniformly dropped with a pipette so as to obtain a predetermined active ingredient amount. In addition, paddy soil is packed in a 1 / 1,000,000 hectare pot, and the paddy depth is 3-4 cm. The next day rice (rice (Oryza sativa L.)) (variety: Nipponbare) is transplanted at a depth of 3 cm. Transplanted. On the day after transplantation, the compound according to the present invention was treated in the same manner as described above.

　薬剤処理後、10～17日目にタイヌビエ、ホタルイ及びウリカワの生育状態を、また薬剤処理後、13～20日目にイネの生育状態を各々肉眼観察し、0（無処理区と同等）～100（完全枯殺）の生育抑制率（％）で評価し、第１７表の結果を得た。 Macroscopically observe the growth of Tainubie, Firefly and Urikawa on the 10th to 17th day after the chemical treatment, and the growth state of the rice on the 13th to 20th day after the chemical treatment. Evaluation was made with a growth inhibition rate (%) of 100 (complete killing), and the results in Table 17 were obtained.

Figure JPOXMLDOC01-appb-T000134
Figure JPOXMLDOC01-appb-T000134

Figure JPOXMLDOC01-appb-T000135
Figure JPOXMLDOC01-appb-T000135

Figure JPOXMLDOC01-appb-T000136
Figure JPOXMLDOC01-appb-T000136

Figure JPOXMLDOC01-appb-T000137
Figure JPOXMLDOC01-appb-T000137

Figure JPOXMLDOC01-appb-T000138
Figure JPOXMLDOC01-appb-T000138

Figure JPOXMLDOC01-appb-T000139
Figure JPOXMLDOC01-appb-T000139

Figure JPOXMLDOC01-appb-T000140
Figure JPOXMLDOC01-appb-T000140

Figure JPOXMLDOC01-appb-T000141
Figure JPOXMLDOC01-appb-T000141

Figure JPOXMLDOC01-appb-T000142
Figure JPOXMLDOC01-appb-T000142

　次に、本発明の製剤例を記載する。 Next, formulation examples of the present invention will be described.

　・製剤例１
（１）本発明に係る化合物　　　　　　　　　　　　　　　　７５　　　重量部
（２）ゲロポンＴ－７７（商品名；ローヌ・プーラン社製）　１４．５　重量部
（３）ＮａＣｌ　　　　　　　　　　　　　　　　　　　　　１０　　　重量部
（４）デキストリン　　　　　　　　　　　　　　　　　　　　０．５　重量部
以上の（１）～（４）の各成分を高速混合細粒機に入れ、さらにそこへ２０％の水を加え造粒、乾燥することにより顆粒水和剤が得られる。 Formulation example 1
(1) Compound according to the present invention 75 parts by weight (2) Geropone T-77 (trade name; manufactured by Rhone-Poulenc) 14.5 parts by weight (3) NaCl 10 parts by weight (4) dextrin 0.5 parts by weight or more Each of the components (1) to (4) is put into a high-speed mixing fine granulator, 20% water is further added thereto, and granulated and dried to obtain a granulated wettable powder.

　・製剤例２
（１）カオリン　　　　　　　　　　　　　　　　　　　　　７８　重量部
（２）ラベリンＦＡＮ（商品名；第一工業製薬（株）製）　　　２　重量部
（３）ソルポール５０３９（商品名；東邦化学工業（株）製）　５　重量部
（４）カープレックス（商品名；ＤＳＬジャパン（株）製）　１５　重量部
以上の（１）～（４）の成分の混合物と本発明に係る化合物とを９：１の重量割合で混合することにより水和剤が得られる。 Formulation example 2
(1) Kaolin 78 parts by weight (2) Labelin FAN (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 2 parts by weight (3) Solpol 5039 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 5 parts by weight (4 ) Carplex (trade name; manufactured by DSL Japan Co., Ltd.) 15 parts by weight or more of the mixture of the components (1) to (4) and the compound according to the present invention are mixed at a weight ratio of 9: 1. A Japanese medicine is obtained.

　・製剤例３
（１）ハイフィラーＮｏ．１０（商品名；松村産業（株）製）　３３　重量部
（２）ソルポール５０５０（商品名；東邦化学工業（株）製）　　３　重量部
（３）ソルポール５０７３（商品名；東邦化学工業（株）製）　　４　重量部
（４）本発明に係る化合物　　　　　　　　　　　　　　　　　６０　重量部
以上の（１）～（４）の各成分を混合することにより水和剤が得られる。 Formulation example 3
(1) High filler No. 10 (trade name; manufactured by Matsumura Sangyo Co., Ltd.) 33 parts by weight (2) Solpol 5050 (trade name; manufactured by Toho Chemical Co., Ltd.) 3 parts by weight (3) Solpol 5073 (trade name; Toho Chemical Industries, Ltd.) 4 parts by weight (4) Compound according to the present invention 60 parts by weight or more of each component (1) to (4) is mixed to obtain a wettable powder.

　・製剤例４
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　　　４　　　重量部
（２）ベントナイト　　　　　　　　　　　　　　　　　　　　　３０　　　重量部
（３）炭酸カルシウム　　　　　　　　　　　　　　　　　　　　６１．５　重量部
（４）トキサノンＧＲ－３１Ａ（商品名；三洋化成工業（株）製）　３　　　重量部
（５）リグニンスルホン酸カルシウム塩　　　　　　　　　　　　　１．５　重量部
予め粉砕した（１）と、（２）及び（３）とを混合し、そこへ（４）、（５）及び水を加えて混合し、押出造粒する。その後、乾燥、整粒することにより粒剤が得られる。 Formulation example 4
(1) Compound according to the present invention 4 parts by weight (2) Bentonite 30 parts by weight (3) Calcium carbonate 61.5 parts by weight (4) Toxanone GR-31A (trade name; manufactured by Sanyo Chemical Industries, Ltd.) 3 parts by weight (5) Lignin sulfonic acid calcium salt 1.5 parts by weight Pre-ground (1), (2) and (3) are mixed, and (4), (5) and water are added and mixed there. Extrude granulate. Then, a granule is obtained by drying and sizing.

　・製剤例５
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　３０　重量部
（２）ジークライト（商品名；ジークライト（株）製）　　　　６０　重量部
（３）ニューカルゲン　ＷＧ－１（商品名；竹本油脂（株）製）　５　重量部
（４）ニューカルゲン　ＦＳ－７（商品名；竹本油脂（株）製）　５　重量部
上記（１）、（２）及び（３）を混合し、粉砕機を通した後、（４）を加えて混練後、押出造粒する。その後、乾燥、整粒することにより顆粒水和剤が得られる。 Formulation example 5
(1) Compound according to the present invention 30 parts by weight (2) Siegrite (trade name; manufactured by Siegrite Co., Ltd.) 60 parts by weight (3) New Calgen WG-1 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 Part by weight (4) New Calgen FS-7 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight After mixing (1), (2) and (3) above and passing through a pulverizer, (4) After kneading and extruding granulation. Thereafter, the wettable powder is obtained by drying and sizing.

　・製剤例６
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　　　２８　重量部
（２）ソプロポールＦＬ（商品名；ローヌ・プーラン社製）　　　　　２　重量部
（３）ソルポール３５５（商品名；東邦化学工業（株）製）　　　　　１　重量部
（４）ＩＰソルベント１６２０（商品名；出光石油化学（株）製）　３２　重量部
（５）エチレングリコール　　　　　　　　　　　　　　　　　　　　６　重量部
（６）水　　　　　　　　　　　　　　　　　　　　　　　　　　　３１　重量部
以上の（１）～（６）の各成分を混合し、湿式粉砕機（ダイノーミル）を用いて粉砕することにより水性懸濁剤が得られる。 Formulation Example 6
(1) Compound according to the present invention 28 parts by weight (2) Sopropol FL (trade name; manufactured by Rhone-Poulenc) 2 parts by weight (3) Solpol 355 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 1 part by weight ( 4) IP solvent 1620 (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) 32 parts by weight (5) ethylene glycol 6 parts by weight (6) water 31 parts by weight or more of the components (1) to (6) were mixed. An aqueous suspension is obtained by pulverization using a wet pulverizer (Dyno mill).

　本発明に係るヘテロアリールスルホンアミド系化合物又はその塩は、類似する従来化合物に比して望ましくない植物への著しい除草活性の向上を実現する。また、作物への高い安全性を有する。それゆえ、本発明に係るヘテロアリールスルホンアミド系化合物又はその塩は、除草剤の有効成分として使用した場合に、優れた除草効果を示す。その適用範囲は、水田、畑地、果樹園、桑園などの農耕地、山林、農道、グランド、工場敷地などの非農耕地と多岐にわたり、適用方法も土壌処理、茎葉処理、湛水処理等を適宜選択できる。 The heteroarylsulfonamide compound or a salt thereof according to the present invention realizes a significant improvement in herbicidal activity against undesirable plants as compared to similar conventional compounds. In addition, it has high safety for crops. Therefore, the heteroaryl sulfonamide compound or a salt thereof according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. The range of application ranges widely from agricultural fields such as paddy fields, upland fields, orchards, mulberry fields, and non-agricultural land such as forests, farm roads, grounds, and factory sites. Applicable methods include soil treatment, foliage treatment, and flooding treatment as appropriate. You can choose.

　尚、２０１１年１０月２５日に出願された日本国特許出願第２０１１－２３４４１０号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。 It should be noted that the entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2011-234410 filed on October 25, 2011 are cited herein as disclosure of the specification of the present invention. Incorporate.

Claims (3)

　一般式（Ｉ）：
Figure JPOXMLDOC01-appb-C000001
 〔式中、Aは酸素原子、硫黄原子、SO、SO2又はCR8R9であり；Wは酸素原子又は硫黄原子であり；Zは酸素原子、硫黄原子又はCR10R11であり；mは0、１又は2であり；nは0、１又は2であり；但し、0≦n+m≦3であり；qは0、１又は2であり；R1はハロC1－C6アルキルであり；R2は水素原子、C1－C12アルコキシカルボニル、C1－C12アルキルカルボニル、ハロC1－C6アルキルカルボニル、シクロC3-C6アルキルカルボニル、シクロC3-C6アルキルC1-C6アルキルカルボニル、C2-C6アルケニルカルボニル、Yで置換されてもよいフェニルC2-C6アルケニルカルボニル、Yで置換されてもよいフェニルカルボニル、Yで置換されてもよい複素環カルボニル、ハロC1－C12アルコキシカルボニル、C1-C6アルキルで置換されてもよいシクロC3-C6アルコキシカルボニル、C2-C6アルケニルオキシカルボニル、ハロC2-C6アルケニルオキシカルボニル、C2-C6アルキニルオキシカルボニル、C1-C6アルコキシC1-C6アルコキシカルボニル、C1-C6アルキルチオC1-C6アルコキシカルボニル、C1-C6アルキルスルフィニルC1-C6アルコキシカルボニル、C1-C6アルキルスルホニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルC1-C6アルコキシカルボニル、Yで置換されてもよいフェニルハロC1-C6アルコキシカルボニル、Yで置換されてもよいフェノキシカルボニル、Yで置換されてもよいフェノキシC1-C6アルキルカルボニル、C1-C6アルキルチオカルボニル、ハロC1-C6アルキルチオカルボニル、モノC1-C6アルキルアミノカルボニル、モノ（ハロC1-C6アルキル）アミノカルボニル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニル、ジ（ハロC1-C6アルキル）アミノカルボニル、C1-C6アルコキシC1-C6アルキルカルボニル、C1-C6アルコキシカルボニルC1-C6アルキルカルボニル、C1-C6アルコキシオキサリル、C1-C6アルキルスルホニル、ハロC1-C6アルキルスルホニル、Yで置換されてもよいフェニルスルホニル、アミノスルホニル、モノC1-C6アルキルアミノスルホニル、ジC1-C6アルキルアミノスルホニル、Yで置換されてもよい複素環スルホニル、シクロC3-C6アルキルスルホニル、C1-C6アルキル、ハロC1-C6アルキル、C2-C6アルケニル、ハロC2-C6アルケニル、C2-C6アルキニル、ハロC2-C6アルキニル、Yで置換されてもよいフェニルC1-C6アルキル、Yで置換されてもよいフェニルカルボニルC1-C6アルキル、C1-C6アルコキシC1-C6アルキル、ハロC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシC1-C6アルコキシC1-C6アルキル、トリC1-C6アルキルシリルC1-C6アルコキシC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルC1-C6アルキル、C1-C6アルキルカルボニルオキシC1-C6アルキル、シクロC3-C6アルキルカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルキル、Yで置換されてもよい複素環カルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルカルボニルオキシC1-C6アルコキシC1-C6アルキル、C1-C6アルコキシカルボニルオキシC1-C6アルキル、シクロC3-C6アルコキシカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェノキシカルボニルオキシC1-C6アルキル、モノC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、窒素原子上の２つのC1-C6アルキルが互いに結合して３～８員環を形成してもよいジC1-C6アルキルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいN-C1-C6アルキル-N-フェニルアミノカルボニルオキシC1-C6アルキル、Yで置換されてもよいフェニルチオC1-C6アルキル、Yで置換されてもよいフェニルスルフィニルC1-C6アルキル、Yで置換されてもよいフェニルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルチオC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルホニルC1-C6アルキル、C1-C6アルキルチオC1-C6アルキル、ハロC1-C6アルキルチオC1-C6アルキル、C1-C6アルキルスルフィニルC1-C6アルキル、C1-C6アルキルスルホニルC1-C6アルキル、Yで置換されてもよいフェニルC1-C6アルキルスルフィニルC1-C6アルキル、チオシアナトC1-C6アルキル、シアノC1-C6アルキル、Yで置換されてもよい複素環C1-C6アルキル、C1-C6アルキルカルボニルC1-C6アルキル又はシアノであり；R3はハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、C1－C6アルキルカルボニル、Yで置換されてもよいフェニル又はシアノであり；R4、R5、R6、R7、R8、R9、R10及びR11は、それぞれ同一又は異なってもよく、水素原子、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C3－C6シクロアルキルC1－C6アルキル、Yで置換されてもよいフェニル、Yで置換されてもよいフェニルC1－C6アルキル、C1－C6アルキルカルボニルオキシ、カルボキシル、C1－C6アルコキシカルボニル、ハロC1－C6アルコキシカルボニル、水酸基又はシアノであり；R4とR5、R6とR7、R8とR9及びR10とR11は各々互いに結合して、任意に置換されてもよい3～7員環を形成することができ、当該3～7員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく、或いは、オレフィン、カルボニル又はチオカルボニルを形成することができ；R4、R5、R6、R7、R8、R9、R10及びR11は、各々が結合する炭素原子とは別の炭素原子上の、任意のR4、R5、R6、R7、R8、R9、 R10又はR11と結合して、任意に置換されてもよい3～8員環を形成することができ、当該3～8員環は酸素原子、硫黄原子又は窒素原子（該窒素原子は、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル又はC3－C6シクロアルキルによって置換されてもよい）から選択される1又は2のヘテロ原子を含んでいてもよく；R4、R5、R6、R7、R8、R9、R10及びR11は、それらが結合する炭素原子と隣り合った炭素原子上の任意のR4、R5、R6、R7、R8、R9、R10又はR11と結合することができ；Yは、ハロゲン原子、C1－C6アルキル、C2－C6アルケニル、C2－C6アルキニル、C1－C6アルキルで置換されてもよいC3－C6シクロアルキル、ハロC1－C6アルキル、ハロC2－C6アルケニル、ハロC2－C6アルキニル、ハロC3－C6シクロアルキル、C1－C6アルコキシ、ハロC1－C6アルコキシ、C1－C6アルキルチオ、ハロC1－C6アルキルチオ、C1－C6アルキルスルフィニル、ハロC1－C6アルキルスルフィニル、C1－C6アルキルスルホニル、ハロC1－C6アルキルスルホニル、カルボキシル、C1－C6アルキルカルボニル、ハロC1－C6アルキルカルボニル、C1－C6アルコキシカルボニル、ハロC1－C6アルコキシ
カルボニル、アミノ、モノ（C1－C6アルキル）アミノ、モノ（ハロC1－C6アルキル）アミノ、ジ（C1－C6アルキル）アミノ、ジ（ハロC1－C6アルキル）アミノ、シアノ、ニトロ又は水酸基であり；前記複素環は、チエニル、フリル、ピロリル、オキサゾリル、イソオキサゾリル、イソオキサゾリニル、チアゾリル、イソチアゾリル、ピラゾリル、イミダソリル、1,3,4-オキサジアゾリル、1,2,4-オキサジアゾリル、1,3,4-チアジアゾリル、1,2,4－チアジアゾリル、1,2,4－トリアゾリル、1,2,3－トリアゾリル、1,2,3－チアジアゾリル、1，2，3，4-テトラゾリル、ピリジル、ピリミジル、ピラジニル、ピリダジニル、1,3,5-トリアジニル、1,2,4-トリアジニル、ベンゾチエニル、ベンゾフリル、インドリル、ベンゾチアゾリル、ベンゾイミダゾリル、ベンゾイソオキサゾリル、ベンゾイソチアゾリル、インダゾリル、ベンゾオキサゾリル、キノリル、イソキノリル、キノキサリニル、フタラジニル、シンノリニル、キナゾリニル、イミダゾリニル、イミダゾリジニル、ピラゾリニル又はピラゾリジニルである〕
で表されるヘテロアリールスルホンアミド系化合物又はその塩。 Formula (I):
Figure JPOXMLDOC01-appb-C000001
 [Wherein A is an oxygen atom, sulfur atom, SO, SO 2 or CR 8 R 9 ; W is an oxygen atom or sulfur atom; Z is an oxygen atom, sulfur atom or CR 10 R 11 ; m Is 0, 1 or 2; n is 0, 1 or 2; provided that 0 ≦ n + m ≦ 3; q is 0, 1 or 2; R 1 is haloC 1 -C 6 R 2 is a hydrogen atom, C 1 -C 12 alkoxycarbonyl, C 1 -C 12 alkylcarbonyl, halo C 1 -C 6 alkylcarbonyl, cyclo C 3 -C 6 alkylcarbonyl, cyclo C 3 -C 6 Alkyl C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, phenyl C 2 -C 6 alkenylcarbonyl optionally substituted with Y, phenylcarbonyl optionally substituted with Y, optionally substituted with Y heterocyclylcarbonyl, halo C 1 -C 12 alkoxycarbonyl, C 1 -C 6 alkyl substituted cyclo C 3 which may be -C 6 alkoxycarbonyl C 2 -C 6 alkenyloxycarbonyl, halo C 2 -C 6 alkenyloxycarbonyl, C 2 -C 6 alkynyloxy-carbonyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylthio C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkoxycarbonyl, phenyl C 1 -C 6 alkoxy optionally substituted by Y carbonyl, Y which may be substituted Feniruharo C 1 -C 6 alkoxycarbonyl, good phenoxycarbonyl which may be substituted by Y, Y-substituted which may phenoxy C 1 -C six alkylcarbonyl, C 1 -C 6 alkylthio Carbonyl, halo C 1 -C 6 alkylthiocarbonyl, mono C 1 -C 6 alkylaminocarbonyl, mono (halo C 1 -C 6 alkyl) aminocarbonyl, two C 1 -C on nitrogen atoms Di-C 1 -C 6 alkylaminocarbonyl, di (halo C 1 -C 6 alkyl) aminocarbonyl, C 1 -C 6 alkoxy C 1-which 6 alkyl may combine with each other to form a 3- to 8-membered ring C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxyoxalyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, optionally substituted with Y Phenylsulfonyl, aminosulfonyl, mono C 1 -C 6 alkylaminosulfonyl, di-C 1 -C 6 alkylaminosulfonyl, heterocyclic sulfonyl optionally substituted with Y, cyclo C 3 -C 6 alkylsulfonyl, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 2 -C 6 alkenyl, halo C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halo C 2 -C 6 alkynyl, optionally substituted with Y Phenyl C 1 -C 6 alkyl, optionally substituted with Y Phenylcarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, halo C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkoxy C 1 -C 6 alkyl, tri-C 1 -C 6 alkylsilyl C 1 -C 6 alkoxy C 1 -C 6 alkyl, phenyl optionally substituted with Y C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 1- C 6 alkoxycarbonyl C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkylcarbonyloxy C 1 -C 6 alkyl, which may be substituted by Y phenyl Carbonyloxy C 1 -C 6 alkyl, heterocyclic carbonyloxy C 1 -C 6 alkyl optionally substituted with Y, phenylcarbonyloxy C 1 -C 6 alkoxy C 1 -C 6 alkyl optionally substituted with Y, C 1 -C 6 alkoxycarbonyloxy C 1 -C 6 alkyl, cyclo C 3 -C 6 alkoxycarbonyloxy C 1 -C 6 Alkyl, phenoxycarbonyloxy C 1 -C 6 alkyl optionally substituted with Y, mono C 1 -C 6 alkylaminocarbonyloxy C 1 -C 6 alkyl, two C 1 -C 6 alkyl on the nitrogen atom coupled to 3- to 8-membered ring formed is also good di C 1 -C six alkylaminocarbonyloxy C 1 -C 6 alkyl, Y-substituted phenyl aminocarbonyl-oxy C 1 -C 6 alkyl, Y NC 1 -C 6 alkyl optionally substituted with N-phenylaminocarbonyloxy C 1 -C 6 alkyl, phenylthio C 1 -C 6 alkyl optionally substituted with Y, phenylsulfinyl optionally substituted with Y C 1 -C 6 alkyl, phenylsulfonyl C 1 -C 6 alkyl optionally substituted with Y, phenyl C 1 -C 6 alkylthio optionally substituted with Y C 1 -C 6 alkyl, optionally substituted with Y phenyl C 1 -C 6 alkylsulfonyl C 1 -C 6 al Le, C 1 -C 6 alkylthio C 1 -C 6 alkyl, halo C 1 -C 6 alkylthio C 1 -C 6 alkyl, C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl, optionally substituted with Y phenyl C 1 -C 6 alkylsulfinyl C 1 -C 6 alkyl, thiocyanato C 1 -C 6 alkyl, cyano C 1 -C 6 alkyl, substituted with Y A heterocycle C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl C 1 -C 6 alkyl or cyano; R 3 is a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, optionally substituted with C 1 -C 6 alkyl C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl Be phenyl or cyano be substituted by Y; R 4, R 5, R 6, R 7, R 8, R 9, R 10 and R 11 may be the same or different, a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl substituted C 3 may be -C 6 cycloalkyl, halo C 1 -C 6 alkyl Halo C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, phenyl optionally substituted by Y, Y Phenyl C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyloxy, carboxyl, C 1 -C 6 alkoxycarbonyl, halo C 1 -C 6 alkoxycarbonyl, hydroxyl or cyano optionally substituted with R 4 ; and R 5, R 6 and R 7, R 8 and R 9 and R 10 and R 11 are each coupled to one another, it may be optionally substituted 3 It is possible to form a 7-membered ring, the 3-7 membered ring is an oxygen atom, a sulfur atom or a nitrogen atom (nitrogen atom, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 May contain 1 or 2 heteroatoms selected from alkynyl or C 3 -C 6 cycloalkyl), or may form an olefin, carbonyl or thiocarbonyl; R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 can be any R 4 , R 5 , R 6 , R on a carbon atom different from the carbon atom to which each is bonded. 7 , R 8 , R 9 , R 10 or R 11 can be combined to form an optionally substituted 3- to 8-membered ring, which is an oxygen atom, sulfur atom or nitrogen atom (the nitrogen atom may be substituted C 1 -C 6 alkyl, C 2 -C 6 alkenyl, by C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl) May contain 1 or 2 heteroatoms et selected; R 4, R 5, R 6, R 7, R 8, R 9, R 10 and R 11, adjacent the carbon atom to which they are attached Can be attached to any R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 on the combined carbon atom; Y is a halogen atom, C 1 -C 6 alkyl , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C may be substituted with alkyl C 3 -C 6 cycloalkyl, halo C 1 -C 6 alkyl, halo C 2 -C 6 alkenyl Halo C 2 -C 6 alkynyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, halo C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, carboxyl, C 1 -C 6 alkylcarbonyl Le, halo C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo C 1 -C 6 alkoxycarbonyl, amino, mono (C 1 -C 6 alkyl) amino, mono (halo C 1 -C 6 alkyl ) Amino, di (C 1 -C 6 alkyl) amino, di (halo C 1 -C 6 alkyl) amino, cyano, nitro or hydroxyl; the heterocycle is thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, iso Oxazolinyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4- Triazolyl, 1,2,3-triazolyl, 1,2,3-thiadiazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4- Triazinyl, Nzothienyl, benzofuryl, indolyl, benzothiazolyl, benzimidazolyl, benzisoxazolyl, benzisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, imidazolinyl, imidazolidinyl, pyrazolidinyl, pyrazolidinyl, pyrazolinyl
Or a salt thereof. 　請求項１に記載のヘテロアリールスルホンアミド系化合物又はその塩を有効成分として含有する除草剤。 A herbicide containing the heteroarylsulfonamide compound according to claim 1 or a salt thereof as an active ingredient. 　請求項１に記載のヘテロアリールスルホンアミド系化合物又はその塩の除草有効量を、望ましくない植物又はそれが生育する場所に施用し、当該望ましくない植物を防除又はその生育を抑制する方法。 A method of applying a herbicidally effective amount of the heteroarylsulfonamide compound or a salt thereof according to claim 1 to an undesired plant or a place where it grows to control the undesired plant or suppress its growth.
PCT/JP2012/077373 2011-10-25 2012-10-23 Heteroaryl sulfonamide compound or salt thereof Ceased WO2013061973A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011234410A JP2015013809A (en) 2011-10-25 2011-10-25 Heteroaryl sulfonamide compound or salt thereof
JP2011-234410 2011-10-25

Publications (1)

Publication Number Publication Date
WO2013061973A1 true WO2013061973A1 (en) 2013-05-02

Family

ID=48167803

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/077373 Ceased WO2013061973A1 (en) 2011-10-25 2012-10-23 Heteroaryl sulfonamide compound or salt thereof

Country Status (2)

Country Link
JP (1) JP2015013809A (en)
WO (1) WO2013061973A1 (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014175206A1 (en) * 2013-04-23 2014-10-30 石原産業株式会社 Heteroarylsulfonamide-type compound or salt thereof
WO2015004282A1 (en) * 2013-07-12 2015-01-15 Syngenta Limited Sulfonamide-heterocyclic herbicidal compounds
WO2015060402A1 (en) * 2013-10-25 2015-04-30 日産化学工業株式会社 Production method for trifluoromethanesulfonanilide compound
WO2015097071A1 (en) 2013-12-25 2015-07-02 Syngenta Participations Ag Herbicidal haloalkylsulphonamide derivatives
WO2016207083A1 (en) * 2015-06-23 2016-12-29 Syngenta Participations Ag Herbicidal compounds
WO2016207082A1 (en) * 2015-06-23 2016-12-29 Syngenta Participations Ag Herbicidal haloalkylsulphonamide compounds
JP2017522374A (en) * 2014-07-02 2017-08-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ Piperidinone herbicide
CN110183455A (en) * 2019-06-18 2019-08-30 中国医科大学 Azabicyclo [3.2.1] octyl- 3- ketone compounds and preparation method thereof and its purposes

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61280491A (en) * 1985-05-30 1986-12-11 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− Herbicidal sulfonamides
JPH04193877A (en) * 1990-11-26 1992-07-13 Mitsui Toatsu Chem Inc 1-(substituted furylmethyl or substituted thenyl)-3-halogeno-4-(1-halogenoalkyl)-2-pyrrolidinone derivative and herbicide containing the same as active ingredient
DE4304288A1 (en) * 1993-02-12 1994-08-25 Hoechst Ag Thienylsulphonylureas, their preparation, and their use as herbicides and plant growth regulators
JPH07501053A (en) * 1991-11-07 1995-02-02 アグレボ・ユー・ケイ・リミテツド sulfonamide herbicide
WO2010026989A1 (en) * 2008-09-02 2010-03-11 日産化学工業株式会社 Ortho-substituted haloalkylsulfonanilide derivative and herbicide
WO2010119906A1 (en) * 2009-04-14 2010-10-21 日産化学工業株式会社 Haloalkylsulfonanilide derivative

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61280491A (en) * 1985-05-30 1986-12-11 イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− Herbicidal sulfonamides
JPH04193877A (en) * 1990-11-26 1992-07-13 Mitsui Toatsu Chem Inc 1-(substituted furylmethyl or substituted thenyl)-3-halogeno-4-(1-halogenoalkyl)-2-pyrrolidinone derivative and herbicide containing the same as active ingredient
JPH07501053A (en) * 1991-11-07 1995-02-02 アグレボ・ユー・ケイ・リミテツド sulfonamide herbicide
DE4304288A1 (en) * 1993-02-12 1994-08-25 Hoechst Ag Thienylsulphonylureas, their preparation, and their use as herbicides and plant growth regulators
WO2010026989A1 (en) * 2008-09-02 2010-03-11 日産化学工業株式会社 Ortho-substituted haloalkylsulfonanilide derivative and herbicide
WO2010119906A1 (en) * 2009-04-14 2010-10-21 日産化学工業株式会社 Haloalkylsulfonanilide derivative

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014175206A1 (en) * 2013-04-23 2014-10-30 石原産業株式会社 Heteroarylsulfonamide-type compound or salt thereof
WO2015004282A1 (en) * 2013-07-12 2015-01-15 Syngenta Limited Sulfonamide-heterocyclic herbicidal compounds
WO2015060402A1 (en) * 2013-10-25 2015-04-30 日産化学工業株式会社 Production method for trifluoromethanesulfonanilide compound
WO2015097071A1 (en) 2013-12-25 2015-07-02 Syngenta Participations Ag Herbicidal haloalkylsulphonamide derivatives
JP2017522374A (en) * 2014-07-02 2017-08-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ Piperidinone herbicide
JP2020143141A (en) * 2014-07-02 2020-09-10 エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ Piperidinone herbicides
JP7088984B2 (en) 2014-07-02 2022-06-21 エフ エム シー コーポレーション Piperidinone herbicide
WO2016207083A1 (en) * 2015-06-23 2016-12-29 Syngenta Participations Ag Herbicidal compounds
WO2016207082A1 (en) * 2015-06-23 2016-12-29 Syngenta Participations Ag Herbicidal haloalkylsulphonamide compounds
CN110183455A (en) * 2019-06-18 2019-08-30 中国医科大学 Azabicyclo [3.2.1] octyl- 3- ketone compounds and preparation method thereof and its purposes
CN110183455B (en) * 2019-06-18 2021-04-20 中国医科大学 Azabicyclo[3.2.1]octan-3-one compounds, preparation method and use thereof

Also Published As

Publication number Publication date
JP2015013809A (en) 2015-01-22

Similar Documents

Publication Publication Date Title
JP6884980B2 (en) Pyridadinone compounds or salts thereof, and herbicides containing them
JP5225657B2 (en) Benzoylpyrazole compounds, methods for producing them, and herbicides containing them
CA2724355C (en) Pyrazole compounds, process for their production and herbicides containing them
WO2010067895A1 (en) Herbicidal compositions containing benzoylpyrazole compounds
JP2009013161A (en) Herbicidal composition containing benzoylpyrazole compound
WO2013061973A1 (en) Heteroaryl sulfonamide compound or salt thereof
JP5420169B2 (en) Herbicides containing benzoylpyrazole compounds
WO2014126070A1 (en) Triazinone carboxamide compound or salt thereof
WO2016056565A1 (en) Arylsulfonamide compound or salt thereof, and herbicide containing same
JP2017075131A (en) Pyridazinone compound or salt thereof, and herbicide comprising them
WO2019065283A1 (en) Pyridazinone compound or salt thereof and herbicide containing same
JP2016128386A (en) Heteroarylsulfonamide-based compound or salt thereof
WO2018135649A1 (en) Isoxazolin-5-one derivative and herbicide containing same as active ingredient
JP2010006798A (en) Benzoylpyrazole-based compound, method for producing the same, and herbicide containing the same
JP2016079121A (en) Heteroaryl sulfonamide compound and herbicide comprising the same
JP2016113449A (en) Heteroaryl sulfonamide compound, salt thereof and herbicide containing them

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12843586

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12843586

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: JP