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WO2013061973A1 - Composé de sulfonamide hétéroaryle ou sel de celui-ci - Google Patents

Composé de sulfonamide hétéroaryle ou sel de celui-ci Download PDF

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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
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Prior art keywords
alkyl
halo
optionally substituted
alkoxycarbonyl
atom
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English (en)
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
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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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.

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  • 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

La présente invention concerne un nouvel herbicide ayant une activité herbicide excellente sur les végétaux indésirables. Le composé de sulfonamide hétéroaryle ou son sel présente une structure représentée par la formule générale (I) : [dans la formule, A est un atome d'oxygène, un atome de soufre, SO, SO2, ou CR8R9 ; W est un atome d'oxygène ou un atome de soufre ; Z est un atome d'oxygène, un atome de soufre ou CR10R11 ; m vaut 0, 1, ou 2 ; n vaut 0, 1, ou 2 ; avec 0≦n+m≦3 ; q vaut 0, 1, ou 2 ; R1 est un groupe halogénoalkyle ; R2 est un atome d'hydrogène, un groupe alkoxycarbonyle, ou similaire ; R3 est un atome d'halogène, un groupe alkyle, cycloalkyle facultativement substitué par un groupe alkyle, halogénoalkyle, halogénocycloalkyle, alkylsulfonyle, alkylcarbonyle, phényle facultativement substitué par Y, cyano, ou similaire ; R4, R5, R6, R7, R8, R9, R10, et R11 peuvent être identiques ou différents et sont un atome d'hydrogène, un atome d'halogène, un groupe alkyle, ou similaire].
PCT/JP2012/077373 2011-10-25 2012-10-23 Composé de sulfonamide hétéroaryle ou sel de celui-ci Ceased WO2013061973A1 (fr)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014175206A1 (fr) * 2013-04-23 2014-10-30 石原産業株式会社 Composé de type heteroarylsulfonamide ou sel de celui-ci
WO2015004282A1 (fr) * 2013-07-12 2015-01-15 Syngenta Limited Composés herbicides hétérocycliques de sulfonamide
WO2015060402A1 (fr) * 2013-10-25 2015-04-30 日産化学工業株式会社 Procédé de production d'un composé trifluorométhanesulfonanilide
WO2015097071A1 (fr) 2013-12-25 2015-07-02 Syngenta Participations Ag Dérivés haloalkylsulphonamide herbicides
WO2016207082A1 (fr) * 2015-06-23 2016-12-29 Syngenta Participations Ag Composés haloalkylsulphonamide herbicides
WO2016207083A1 (fr) * 2015-06-23 2016-12-29 Syngenta Participations Ag Composés herbicides
JP2017522374A (ja) * 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 ピペリジノン除草剤
CN110183455A (zh) * 2019-06-18 2019-08-30 中国医科大学 氮杂双环[3.2.1]辛-3-酮类化合物及其制备方法与其用途

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DE4304288A1 (de) * 1993-02-12 1994-08-25 Hoechst Ag Thienylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
JPH07501053A (ja) * 1991-11-07 1995-02-02 アグレボ・ユー・ケイ・リミテツド スルホンアミド除草剤
WO2010026989A1 (fr) * 2008-09-02 2010-03-11 日産化学工業株式会社 Dérivé halogénoalkylsulfonanilide ortho-substitué et herbicide
WO2010119906A1 (fr) * 2009-04-14 2010-10-21 日産化学工業株式会社 Dérivés d'haloalkylsulfonanilide

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JPS61280491A (ja) * 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− 除草剤性スルホンアミド類
JPH04193877A (ja) * 1990-11-26 1992-07-13 Mitsui Toatsu Chem Inc １―（置換フリルメチルまたは置換テニル）―３―ハロゲノ―４―（１―ハロゲノアルキル）―２―ピロリジノン誘導体およびこれらを有効成分とする除草剤
JPH07501053A (ja) * 1991-11-07 1995-02-02 アグレボ・ユー・ケイ・リミテツド スルホンアミド除草剤
DE4304288A1 (de) * 1993-02-12 1994-08-25 Hoechst Ag Thienylsulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2010026989A1 (fr) * 2008-09-02 2010-03-11 日産化学工業株式会社 Dérivé halogénoalkylsulfonanilide ortho-substitué et herbicide
WO2010119906A1 (fr) * 2009-04-14 2010-10-21 日産化学工業株式会社 Dérivés d'haloalkylsulfonanilide

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014175206A1 (fr) * 2013-04-23 2014-10-30 石原産業株式会社 Composé de type heteroarylsulfonamide ou sel de celui-ci
WO2015004282A1 (fr) * 2013-07-12 2015-01-15 Syngenta Limited Composés herbicides hétérocycliques de sulfonamide
WO2015060402A1 (fr) * 2013-10-25 2015-04-30 日産化学工業株式会社 Procédé de production d'un composé trifluorométhanesulfonanilide
WO2015097071A1 (fr) 2013-12-25 2015-07-02 Syngenta Participations Ag Dérivés haloalkylsulphonamide herbicides
JP2017522374A (ja) * 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 ピペリジノン除草剤
JP2020143141A (ja) * 2014-07-02 2020-09-10 エフ エム シー コーポレーションＦｍｃ Ｃｏｒｐｏｒａｔｉｏｎ ピペリジノン除草剤
JP7088984B2 (ja) 2014-07-02 2022-06-21 エフ エム シー コーポレーション ピペリジノン除草剤
WO2016207082A1 (fr) * 2015-06-23 2016-12-29 Syngenta Participations Ag Composés haloalkylsulphonamide herbicides
WO2016207083A1 (fr) * 2015-06-23 2016-12-29 Syngenta Participations Ag Composés herbicides
CN110183455A (zh) * 2019-06-18 2019-08-30 中国医科大学 氮杂双环[3.2.1]辛-3-酮类化合物及其制备方法与其用途
CN110183455B (zh) * 2019-06-18 2021-04-20 中国医科大学 氮杂双环[3.2.1]辛-3-酮类化合物及其制备方法与其用途

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