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WO2005118530A1 - Composés de triketone, leur méthode de producion et celle d’herbicides les contenant - Google Patents

Composés de triketone, leur méthode de producion et celle d’herbicides les contenant Download PDF

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Publication number
WO2005118530A1
WO2005118530A1 PCT/JP2005/010189 JP2005010189W WO2005118530A1 WO 2005118530 A1 WO2005118530 A1 WO 2005118530A1 JP 2005010189 W JP2005010189 W JP 2005010189W WO 2005118530 A1 WO2005118530 A1 WO 2005118530A1
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alkyl
compound
formula
hydrogen atom
reaction
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Japanese (ja)
Inventor
Yuji Nakamura
Makiko Sano
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Ishihara Sangyo Kaisha Ltd
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Ishihara Sangyo Kaisha Ltd
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Priority to CN2005800178357A priority Critical patent/CN1960967B/zh
Priority to KR1020127028049A priority patent/KR20120123735A/ko
Priority to KR1020067025326A priority patent/KR101225441B1/ko
Publication of WO2005118530A1 publication Critical patent/WO2005118530A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
    • C07C329/02—Monothiocarbonic acids; Derivatives thereof
    • C07C329/04—Esters of monothiocarbonic acids
    • C07C329/06—Esters of monothiocarbonic acids having sulfur atoms of thiocarbonic groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention relates to triketone compounds, methods for producing them, and herbicides containing them.
  • the present invention relates to a novel triketone compound useful as an active ingredient of a herbicide, a method for producing the same, and a herbicide containing them.
  • Triketone compounds which are active ingredients of herbicides are described in Patent Document 1, Patent Document 2, Patent Document 3, and the like. However, these are different from the triketone compounds represented by the formula (I) of the present invention described below.
  • Patent Document 1 JP-A-6-271562
  • Patent Document 2 JP-A-7-206808
  • Patent Document 3 International Publication WO2001Z14303
  • An object of the present invention is to provide a novel triketone compound useful as an active ingredient of a herbicide, a method for producing the same, and a herbicide containing them.
  • the present invention provides a compound represented by the formula (I):
  • y is an integer of 1 to 6
  • A is a 5- or 6-membered saturated heterocyclic group containing at least one heteroatom selected from the group consisting of an oxygen atom and a sulfur atom.
  • Heterocycle R 1 is halogen
  • R 2 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloanolequinolethio, a Nolequinoresnorefinole, haloanolequinolenesolefininole, anolequinolenesolenor, haloalkylsulfol, dialkylaminosulfol, di (noalkyl) aminosulfol, nitro or cyano Yes
  • R 7 and R 8 are each a hydrogen atom or alkyl
  • R 5 is a hydrogen atom, alkyl or cycloalkyl
  • R 5 and R 8 may be taken together to form a 3- to 6-membered saturated carbon ring.
  • R 5 and R 6 can be combined to form a ketone
  • Q is a hydrogen atom
  • -C ( 0)-(CH) -R 9
  • -C ( L)-M-R 9
  • - C ( L) - N (R 9)
  • R 9 R 1Q or -SO-R 9 , L and M are each an oxygen atom or a sulfur atom, and n is 0-3
  • R 9 and R 1Q are each a hydrogen atom, alkyl, alkoxyalkyl, alkoxy, optionally substituted phenyl or optionally substituted benzyl, and R 9 and R 1Q are taken together
  • a 5- or 6-membered saturated heterocyclic group may be formed, except that y is 1 and A is 1,3 dioxane 2 yl or 1, 3 dioxolan 2 yl.
  • the present invention relates to a triketone compound represented by the formula or a salt thereof, a method for producing them, and a herbicide containing them.
  • R 9 and unsubstituted or Yo in R 1Q, Hue - Le or unsubstituted or Yo, as its location substituent benzyl for example, halogen, alkyl, haloalkyl, alkoxy, Haroarukoki shea, alkylthio, halo Alkylthio, alkylsulfyl, haloalkylsulfur, alkylsulfol, haloalkylsulfol, nitro, cyano and the like.
  • the number of the substituents may be 1 or 2 or more. When the number is 2 or more, each substituent may be the same or different.
  • the substitution position of each substituent may be any position.
  • R 9 and R 1Q may be taken together to form a 5- or 6-membered saturated heterocyclic group.
  • saturated heterocyclic group include pyrrolidinyl, piberidyl, morpholinyl and the like.
  • the alkyl or alkyl moiety in R 5 , R 6 , R 7 , R 8 , R 9 and R 1Q is a straight-chain or branched one having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, propyl Isopropyl, butyl, tert-butyl, pentyl, hexyl and the like.
  • the cycloalkyl in R 5 those having 3 to 4 carbon atoms, such as cyclopropyl, cyclo Butyl and the like.
  • halogen or halogen moiety in R 9 and R 1q fluorine, chlorine, an atom of bromine or iodine.
  • the number of halogen substitution as a substituent is 1 or 2 or more. When the number is 2 or more, each halogen may be the same or different. In addition, the replacement position of halogen may be shifted! /.
  • Examples of the 5- or 6-membered saturated heterocyclic group containing 1 to 2 at least one heteroatom selected from the group consisting of oxygen atom and sulfur nuclear atom in A include tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, dioxolan-1-yl, dioxolan-1-yl, tetrahydropyran-12-yl, 1,4-dioxane-1-yl, 1,3-dioxane-12-yl, 1,1 3 dioxan-4yl, tetrahydrothiophen-2-yl, tetrahydrothiopyran-2yl, 1,3 dithiane-2yl, 1,4-dithiane-2yl, 1,4-thioxan-2-yl, 1,4thioxan-3- And the like.
  • the heterocyclic group may be substituted with alkyl having 1 to 6 carbon atoms!
  • R 5 and R 8 may be combined to form a 3- to 6-membered saturated carbocyclic ring, for example, a compound represented by the following formula.
  • R 5 and R 6 are a represented by reduction Gobutsu formula as Yogu example below also form a connexion ketones such together.
  • the triketone-based compound represented by the formula (I) can form a salt.
  • Salts include any agriculturally acceptable salts such as alkali metal salts such as sodium, potassium, and lithium salts; alkaline earth salts such as magnesium, calcium, and norium salts. Metal salts; ammonium salts such as NH 4+ salts, dimethylamine salts, and triethylamine salts.
  • the triketone compound represented by the formula (I) has various isomers, for example, tautomers and optical isomers. In the present invention, each isomer and a mixture of isomers are included. Both are included. In the present invention, various isomers other than those described above are also included within the scope of common technical knowledge in the technical field. Further, depending on the type of the isomer, the chemical structure may be different from the formula (I), but those skilled in the art can fully recognize that they are in an isomer relationship, It is clear that it is within the range.
  • the triketone-based compound represented by the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following reaction [A] to] or an ordinary salt production method.
  • reaction [A] can be usually performed in the presence of a base and a solvent.
  • Bases include, for example, sodium methoxide, sodium ethoxide, potassium tertiary butoxy.
  • Alkali metal alkoxides such as sides; carbonates such as sodium carbonate and potassium carbonate; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine, and triethylamine; pyridine; One or more of pyridines such as dimethylaminopyridine can be appropriately selected.
  • the base can be used in 1 to 3 moles, preferably 1 to 2 moles, relative to the compound of the formula (1-1).
  • any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • Aliphatic hydrocarbons such as methyl chloride, chloroform, dichloromethane, dichloroethane, and trichloroethane
  • esters such as dioxane, tetrahydrofuran, methyl ethyl acetate, and ethyl acetate
  • Polar aprotic solvents such as dimethylformamide, N-methylpyrrolidone and pyridine
  • -tolyls such as acetonitrile and propio-tolyl
  • one or more kinds of ketones such as acetone and methylethylketone Can be appropriately selected.
  • the reaction temperature of the reaction (A) is usually 20 to + 50 ° C, preferably 0 to 30 ° C, and the reaction time is usually 0.1 to 12 hours, preferably 0.5 to 2 hours. .
  • Reaction can be carried out usually in the presence of a base and a solvent.
  • a base for example, one or more kinds can be appropriately selected from those exemplified in the above reaction [A].
  • the base can be used 1 to 3 times, preferably 1 to 2 times the mole of the compound of the formula (I 1).
  • any solvent may be used as long as it is inert to the reaction.
  • One or more kinds can be appropriately selected from those listed in the reaction [A].
  • the reaction temperature of the reaction [B] is usually 0 to: LOO ° C, preferably 0 to 50 ° C, and the reaction time is usually 1 to 120 hours, preferably 1 to 24 hours.
  • Reaction can be carried out usually in the presence of a base and a solvent.
  • a base for example, one or more kinds can be appropriately selected from those exemplified in the above reaction [A].
  • the base can be used 1 to 3 times, preferably 1 to 2 times the mole of the compound of the formula (I 1).
  • any solvent may be used as long as it is inert to the reaction.
  • one or more solvents can be appropriately selected from those mentioned in the above-mentioned reaction [A].
  • the reaction temperature of the reaction [C] is usually 0 to 50 ° C, preferably 0 to 30 ° C, and the reaction time is usually 1 to 24 hours, preferably 1 to 12 hours.
  • Reaction [D] can be usually performed in the presence of a base, a cyanide compound and a solvent.
  • the base include one or more tertiary amines such as trialkylamine, trialkanolamine, and pyridine; and carbonates such as sodium carbonate and potassium carbonate. It can be selected as appropriate.
  • the base can be used 1 to 4 times, preferably 2 to 3 times the mole of the compound of the formula (II).
  • cyanide compound for example, one or two or more of alkali metal cyanides such as sodium cyanide and potassium cyanide; cyanohydrins such as acetone cyanohydrin, methyl isobutyl ketone cyanohydrin, and benhydrin are appropriately used. You can choose.
  • the cyanide compound can be used in an amount of 0.01 to 0.5 times, preferably 0.1 to 0.2 times the mole of the compound of the formula (II).
  • any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • Aliphatic hydrocarbons such as methyl, chlorophonolem, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane
  • esters such as methyl acetate and ethyl acetate
  • one or more polar aprotic solvents such as acetonitrile, propio-tolyl, and acrylonitrile.
  • Reaction [D] can be carried out in the presence of a phase transfer catalyst, if necessary.
  • phase transfer catalyst include crown ethers.
  • the reaction temperature of the reaction (D) is usually 0 to 50 ° C., preferably room temperature, and the reaction time is usually
  • y, A, R 7 and R 8 are as described above, is alkyl or haloalkyl, and m is 1 or 2.
  • Reaction can be carried out usually in the presence of an oxidizing agent and a solvent.
  • an oxidizing agent for example, one or more of peroxybenzoic acid, hydrogen peroxide, peracetic acid, tert-butylino, peroxide at the mouth can be appropriately selected.
  • the oxidizing agent can be used in an amount of 1 to 5 times, preferably 1 to 3 times the mole of the compound of the formula (I 1).
  • any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • Aliphatic hydrocarbons such as methyl, chlorophonolem, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane
  • esters such as methyl acetate and ethyl acetate
  • methanol, ethanol, propanol and tert-butanol One or more of such alcohols; organic acids such as acetic acid and propionic acid; and water can be appropriately selected.
  • the reaction temperature of the reaction (E) is usually from 20 to + 100 ° C, preferably from 5 to + 50 ° C, and the reaction time is usually from 0.1 to 48 hours, preferably from 0.1 to 48 hours. 24 hours.
  • the compound of formula (II) (enol ester) used in the reaction [D] can be produced according to the following reaction [F] or [G].
  • Reaction [F] can be usually performed in the presence of a base and a solvent.
  • the base examples include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tert-butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium bicarbonate and sodium bicarbonate.
  • Bicarbonates such as potassium carbonate; metal hydroxides such as sodium hydroxide and potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; monomethylamine, dimethylamine, triethylamine
  • amines such as amines and pyridines such as pyridine and 4-dimethylaminopyridine can be appropriately selected.
  • the base can be used 1 to 3 times, preferably 1 to 1.5 times, the mole of the compound of the formula (IV).
  • any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • Aliphatic hydrocarbons such as methyl, chlorophonolem, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane
  • ethers such as dioxane, tetrahydrofuran, and ethyl ether; such as methyl acetate and ethyl acetate Esters
  • polar aprotic solvents such as dimethyl sulfoxide, sulfolane, dimethylacetamide, dimethylformamide, N-methylpyrrolidone, pyridine
  • nitriles such as acetonitrile, propio-tolyl, Atari-mouth nitrile
  • acetone Or two from ketones such as, methyl e
  • the reaction temperature of the reaction [F] is usually 0 to 50 ° C, preferably 0 to 30 ° C, and the reaction time is usually 0.5 to 24 hours, preferably 1 to 12 hours.
  • Reaction can be carried out usually in the presence of a dehydrating condensing agent and a solvent.
  • dehydrating condensing agent examples include N, N'-dicyclohexylcarbodiimide and the like.
  • the dehydration condensing agent can be used in an amount of 1 to 3 times, preferably 1 to 1.5 times the mole of the compound of the formula (V).
  • the solvent may be any solvent as long as it is inert to the reaction.
  • tetrachloride carbon methyl chloride, chloroform, dichloromethane, dichloroethane, trichloroethane, hexane, cyclohexane
  • aliphatic hydrocarbons such as You can choose.
  • the reaction temperature of the reaction [G] is usually 0 to 50 ° C, preferably 0 to 30 ° C, and the reaction time is usually 0.5 to 48 hours, preferably 1 to 24 hours.
  • the compound of the formula (IV) used in the reaction [F] can be produced according to the following reaction [H].
  • reaction (H) y, A, R 1 and IT are as defined above.
  • Reaction can be carried out usually in the presence of a chlorinating agent.
  • a chlorinating agent examples include Shio-Dani Zionyl, Shio-Dani Oxalyl and the like.
  • the chlorinating agent can be used in an amount of 1 to 5 times, preferably 1 to 2 times the mole of the compound of the formula (V). Also, the chloridizing agent can double as a solvent if used in excess.
  • Reaction can be carried out 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, and chlorobenzene
  • tetrahydrocarbon methyl chloride, and chloroform
  • Luminous hydrocarbons such as dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane
  • ethers such as dioxane, tetrahydrofuran and getyl ether
  • esters such as methyl acetate and ethyl acetate
  • One or two or more nitriles such as acetonitrile, propio-tolyl, and atarilonitrile
  • ketones such as acetone and methyl ethyl ketone can be appropriately selected.
  • [0044] can be carried out in the presence of a catalyst, if necessary.
  • a catalyst examples include dimethylformamide.
  • the reaction temperature of the reaction [H] is usually 0 to 120 ° C, preferably 20 to 100 ° C, and the reaction time is usually 0.5 to 12 hours, preferably 1 to 4 hours.
  • the compound of the formula (V) used in the reaction (G) or (H) is prepared according to the following reaction (I) Can be manufactured.
  • reaction [I] y, A, R 1 and R 2 are as described above, and R 15 is alkyl.
  • Reaction [I] can be carried out according to a general hydrolysis reaction, and can be usually carried out in the presence of a base and a solvent.
  • the base examples include metal hydroxides such as sodium hydroxide and potassium hydroxide.
  • the base can be used in an amount of 1 to 5 moles, preferably 1 to 3 moles relative to the compound of the formula (VI).
  • any solvent may be used as long as it is inert to the reaction.
  • -tolyls such as acetonitrile, propio-tolyl, and acrylonitrile
  • ketones such as acetone and methylethylketone
  • methanol One or more of alcohols such as ethanol, propanol, and tert-butanol
  • ethers such as dioxane, tetrahydrofuran and getyl ether; and water can be appropriately selected.
  • the reaction temperature of the reaction [I] is usually 0 to: LOO ° C, preferably 0 to 30 ° C, and the reaction time is usually 0.1 to 24 hours, preferably 3 to 20 hours.
  • the compound of the formula (VI) used in the reaction [I] can be produced according to the following reactions Ci] to [M].
  • G is a hydroxyl group, a chlorine atom or a It is a bromine atom.
  • Reaction ⁇ can be usually performed in the presence of a solvent.
  • the solvent may be any solvent as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and chlorobenzene; tetrachlorosilane, methyl chloride, Aliphatic hydrocarbons such as chloroform, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and getyl ether; esters such as methyl acetate and ethyl acetate Polar aprotic solvents such as dimethylsulfoxide, sulfolane, dimethylacetamide, dimethylformamide, ⁇ -methylpyrrolidone and pyridine; -tolyls such as acetonitrile, propio-tolyl, acrylonitrile; ace
  • Reaction Ci] can be carried out in the presence of a base, if necessary.
  • the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide; Metal hydroxides such as potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; pyridine and 4-dimethylaminopyridine One or more kinds of pyridines can be appropriately selected.
  • the base can be used in an amount of 1 to 5 moles, preferably 1 to 3 moles, per 1 mole of the starting carboxylic acid compound.
  • Reaction Ci] can be carried out in the presence of a dehydrating condensing agent, if necessary.
  • a dehydrating condensing agent for example, one or more of triphenylphosphine, getyl azodicarboxylate and the like can be appropriately selected.
  • the dehydrating condensing agent can be used in an amount of 1 to 5 times, preferably 1 to 2 times the mol of the carboxylic acid compound as a starting material.
  • the reaction temperature of the reaction Ci] is usually 0 to 150 ° C, preferably 0 to 120 ° C, and the reaction time is usually 0.5 to 24 hours, preferably 1 to 20 hours.
  • Reaction [K] can be usually performed in the presence of a solvent.
  • the solvent may be any solvent that is inert to the reaction, for example, aromatic hydrocarbons such as benzene, toluene, xylene, and benzene; chlorosilane, methyl chloride, and methyl chloride.
  • Aliphatic hydrocarbons such as form, dichloromethane, dichloroethane, trichloroethane, hexane and cyclohexane; ethers such as dioxane, tetrahydrofuran and getyl ether; dimethyl sulfoxide, sulfolane, dimethylacetamide,
  • polar aprotic solvents such as dimethylformamide, dimethylpyrrolidone, and pyridine.
  • the reaction [ ⁇ ⁇ ] can be carried out in the presence of a base, if necessary.
  • the base include alkali metals such as sodium and potassium; alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; sodium hydroxide; Metal hydroxides such as potassium hydroxide; metal hydrides such as sodium hydride and potassium hydride; amines such as monomethylamine, dimethylamine and triethylamine; pyridine and 4-dimethylaminopyridine One or more kinds of pyridines can be appropriately selected.
  • the base can be used in an amount of 1 to 5 times, preferably 1 to 3 times the mole of the compound of the formula (VI-1).
  • the reaction temperature of the reaction [ ⁇ ] is usually 0 to 150 ° C, preferably 20 to 120 ° C, and the reaction time is usually 0.1 to 72 hours, preferably 0.2 to 24 hours.
  • Reaction [L] can be usually performed in the presence of an oxidizing agent and a solvent.
  • oxidizing agent for example, one or more of peroxybenzoic acid, peroxybenzoic acid, hydrogen peroxide, peracetic acid, tert-butylino, peroxide at the mouth, etc. can be appropriately selected.
  • the oxidizing agent can be used in an amount of 1 to 5 times, preferably 1 to 3 times the mole of the compound of the formula (VI-2).
  • any solvent may be used as long as it is inert to the reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, and benzene benzene
  • Fatty hydrocarbons such as methyl, chlorohonolem, dichloromethane, dichloroethane, trichloroethane, hexane, and cyclohexane
  • esters such as methyl acetate and ethyl acetate
  • methanol, ethanol, propanol, tert-butanol One or more kinds can be appropriately selected from alcohols such as organic acids such as acetic acid and propionic acid; and water.
  • the reaction temperature of the reaction (L) is usually -20 to + 100 ° C, preferably -5 to + 50 ° C, and the reaction time is usually 0.1 to 48 hours, preferably 0.1 to 24 hours. Time.
  • R 2 and R are as described above, R 16 is a hydrogen atom or alkyl, y is an integer of 2 to 6, and p is 0 or 1.
  • the reaction [M] can be usually performed in the presence of an acid and a solvent.
  • Examples of the acid include organic acids such as p-toluenesulfonic acid; and mineral acids such as sulfuric acid, hydrochloric acid, and nitric acid.
  • any solvent may be used as long as it is inert to the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene, xylene, and benzene.
  • the reaction temperature of the reaction [M] is usually 80 to 150 ° C, preferably 100 to 130 ° C, and the reaction time is usually 0.1 to 12 hours, preferably 0.5 to 5 hours. is there.
  • the compound of the formula (VII) used in the above reaction [M] can be produced according to the following reaction [N].
  • [N] can be usually carried out in the presence of an acid and a solvent.
  • Examples of the acid include mineral acids such as sulfuric acid, hydrochloric acid, and nitric acid.
  • the solvent may be any solvent that is inert to the reaction, for example, ethers such as dioxane, tetrahydrofuran, and getyl ether; -tolyls such as acetonitrile, propio-tolyl, and acrylonitrile; acetone And ketones such as methylethyl ketone; alcohols such as methanol, ethanol, propanol and tert-butanol
  • ethers such as dioxane, tetrahydrofuran, and getyl ether
  • -tolyls such as acetonitrile, propio-tolyl, and acrylonitrile
  • acetone And ketones such as methylethyl ketone
  • alcohols such as methanol, ethanol, propanol and tert-butanol
  • One or more of water and the like can be appropriately selected.
  • the reaction temperature of the reaction [N] is usually 0 to 100 ° C, preferably 0 to 30 ° C, and the reaction time is
  • the time is usually 0.1 to 12 hours, preferably 0.5 to 4 hours.
  • Reaction [o] can be carried out according to the aforementioned reaction Ci].
  • the compound of the present invention shows an excellent herbicidal effect when used as an active ingredient of a herbicide.
  • the range of application covers a wide range of agricultural land, such as paddy fields, fields, orchards, and mulberry fields, and non-agricultural land such as forests, farm roads, grands, and factory sites. You can choose.
  • the compound of the present invention includes, for example, grasshoppers such as grasshopper, grasshopper moss, scrophulariformes, scrophulariformes, scrophulariformes, scrophulariformes, spruce millet, paragrass, azegaya, itazegaya, scrophulariformes, moss, sarcophagia, sarcophagia, saccharomyces chinensis, sorghum, oak sorghum, oak sorghum, seyvan sorghum, cinna rye, velvet cane, paragrass, azegaya, itozegaya, sylvestris.
  • grasshoppers such as grasshopper, grasshopper moss, scrophulariformes, scrophulariformes, scrophulariformes, scrophulariformes, spruce millet, paragrass, azegaya, itazegaya,
  • Weedy weeds such as masuge, yellow flies, fireflies, mizugayari, tamagayari, pine bye, kuroguwai etc.
  • weeds of the family Laminariaceae such as the pygmy beetle, and the lycopogonaceae
  • weeds malva morning glory, shiroza, American sika deer, suberichu, aobu, aogetou, ebisudasa, inuhozuki, sa
  • It can control harmful weeds such as broadleaf weeds, such as edade, hakobe, honamemi, tanekebana, pokeweed, ragweed, yaemdara, sycamoreus, daffodil asagao, ezonokinnezami, enokigusa, and other useful crops such as maize.
  • the compound of the present invention is effectively used in the cultivation of corn, wheat, rice and the like, and particularly in the case of selectively controlling harmful weeds in the cultivation of rice.
  • the compound of the present invention is usually mixed with various agricultural auxiliaries to prepare powders, granules, wettable powders, hydrates, aqueous suspensions, oil suspensions, aqueous solvents, emulsions, tablets, capsules, etc.
  • Auxiliaries that can be used in the formulation include diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, linoleum, bentonite, a mixture of kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch Solid carriers such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, benzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, N-methyl-2-pyrrolidone, alcohol Solvents such as fatty acid salts, benzoates, alkyl sulfosuccinates, dialkyl sulfosuccin
  • adjuvants can be selected from those known in the art without departing from the purpose of the present invention.
  • various commonly used auxiliary agents such as a bulking agent, a thickener, an antisettling agent, an antifreezing agent, a dispersion stabilizer, a safener, and a fungicide can be used. Damage to rooster by the compound of the present invention and various adjuvants
  • the application rate of the herbicide containing the compound of the present invention cannot be specified unconditionally due to differences in weather conditions, soil conditions, preparation form, type of target weed, application time, and the like.
  • the application is such that the compound weighs 0.5 to 5000 g, preferably 1 to: L000 g, more preferably 5 to 500 g.
  • the present invention also includes a method for controlling harmful weeds by applying such a herbicide.
  • the herbicide containing the compound of the present invention can be mixed with or used in combination with other agricultural chemicals, fertilizers, safeners, and the like. is there.
  • Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides, and the like.
  • a mixed herbicidal composition in which the compound of the present invention and one or more other herbicidal active ingredient compounds are mixed or used in combination has a range of applicable herb species, time of chemical treatment, herbicidal activity, etc. It is possible to improve in a favorable direction.
  • the compound of the present invention and the other herbicidal active ingredient compounds may be prepared separately and mixed at the time of spraying, or both may be prepared together and used.
  • the present invention also includes the above-mentioned mixed herbicidal composition.
  • the mixing ratio of the compound of the present invention to other herbicide active ingredient compounds cannot be unconditionally specified due to differences in weather conditions, soil conditions, drug formulation, application time, application method and the like.
  • Other herbicides contain 0.001 to 10,000 parts by weight, preferably 0.01 to L000 parts by weight of the active ingredient compound per one part by weight.
  • the suitable amount of application is 0.1 to: L0000 g, preferably 0.2 to 5000 g, as the total amount of the active ingredient per hectare.
  • the present invention also includes a method for controlling harmful weeds by applying such a mixed herbicidal composition.
  • herbicide active ingredient ⁇ conjugates include the following (generic name; ) Can be exemplified. Even when there is no particular description, when salts, alkyl esters, and the like exist in these compounds, they naturally are included.
  • (0072) such as chlorotoluron, diuron, fluometuron, liuron, linuron, isoproturon, metobenzuron, and tebuthiuron Urea, simazine, atrazine, atrazine, atratone, simethrin (simetryn), promethrin (prometryn), dimethamethrin (dimimemetryn), hexazinone (hexazinone), metribuzin, tenoretbutylazine, terbuthylazine , Nonanine (cyanazine), methrin (ametryn), mbutrin (cybutryne), triaziflam (triaziflam), triazines such as propazine (propazine), bromacinole (bromacil), renacil (lenacil), terabacil (terbacil), etc.
  • simazine simethrin (simetryn), promethrin (
  • Quaternary ammoniums such as paraquat and diquat, which are themselves considered as free radicals in plants and generate active oxygen to exhibit a rapid herbicidal effect. Salt system.
  • Norflurazon (norflurazon), chloridazon, pyridazinones such as metflurazoon (metflur azon), pyrazolate (pyrazolate), pyrazoxyfen (pyrazoxyfen), benzofenap (benzofenap): BAS—670H
  • pyrazoles amitrol, fluridone, flurtamone, diflufenican, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione, etc.
  • carotenoids such as mesotrione), AVH-301, isoxaflutole, difenzoquat, isoxachlortole, benzobicyclone, benzobicyclone, picolinafen, beflubu tamid Inhibits pigment biosynthesis in plants What it is showing the herbicidal activity characterized.
  • Uron imazosnorefuron (imazosulfuron), cyclosulfamuron (cyclosulfamuron), prosulfuron (prosulforon), flupyrsulluron (flupyrsulluron), trisnoleflon methinole (trisul) , Nodurosnoleflon Methinole (halo sulforon-methyl), Thifensulforon-methyl (thifensulforon-m ethyl), ethoxysulforon, oxasulforon, ethametsu huron, flupyrsulforon, fludorsulforon, iodosulforon, trisulfosulfron, tria Tribenuron-methyl, tritosulforon, foramsulforon, trifloxysulforon, isosulforon-methyl flucetosulforon, flucetosulforon Sul
  • Di-throaline system such as trifluralin, oryzalin, oritralin, nitralin, pendimetalin, pendimethalin, ethalfluralin, benfluralin, benfluralin, and prodiamine , Benzulide, bensulide, napronamide (napronamide), amides such as pronamide (pronamide), amiprofos-methyl (am lprofos-methyl), bufos (butamifos), nilofos, anilofos, Organophosphorus such as piperophos), propham, chlorpropham, phenol carbamate such as barban, daimuron, daimylon, cu myluron, bromobutide ( bromobutide) and other plant materials such as ashram (asul am), dithiopyr, thiazopyr, etc. What it is showing the herbicidal activity by inhibiting Yuitobun cleft.
  • EPTC butylate, vernolate, molinate, hebrate, pebulate, cycloate, cyclopeperate, dimepiperate, mouth Methanol, DSMA, endothall, MSMA, DSMA, endothall, etc., such as sulfokanoleb (prosulfocarb), esprocanoleb (esprocarb), thiobencanoleb (thiobenc arb), pyributicarb (pyributicarb), dialate (diallate), trialate (triallate) Seth (etho! Umesate), sodium chlorate (sodium
  • Xanthomonas campestris Apicoccosurus nematosurus, axseronilum monos eras, Drechsrela monoceras, and the like, which are said to exhibit a dechisti effect by damaging plants.
  • the compounds of the present invention include those having safety for crops such as rice, wheat, and corn, and exhibiting the selectivity of favorably controlling weeds.
  • crops such as rice, wheat, and corn
  • a synergistic effect may be obtained by mixing or using in combination with one or more of the following active ingredient compounds of the other herbicides, for example, the following compounds.
  • Tolazonetil primisulfuron-methyl, limsnorefron, nicos-norefron, prosnorefron, halosnoreflon-methinole, thifensnoreflon-methyl, flumelam, metoslam, imazethapyr, glyphosate ammom-dim, glyphosate isopropylamine, Dalfosinate ammodime salt, trifluralin, pendymethalin, EPTC, butyrate, aralchlor, metolachlor, S-meth Crawl, ⁇ cell Tokuroru, prop crawl, dimethenamid, birds di fan, florasulam, Metobenzuron, Metosurufan, Okisasurufuron, tepraloxydim, Ami force Rubazon, Forum freon
  • Desirable embodiments of the present invention are as follows.
  • R 9 and R 1Q are each a hydrogen atom, alkyl or phenyl which may be substituted, (1) to (3, any of the compounds or salts thereof.
  • A is a 5- or 6-membered saturated heterocyclic group containing 1 to 2 at least one heteroatom selected from the group consisting of an oxygen atom and a sulfur nuclear atom (the heterocyclic group is substituted with alkyl Or the above-mentioned (1)-(5), or a salt thereof.
  • A is a 5- or 6-membered saturated heterocyclic group containing 1 to 2 at least one heteroatom selected from the group consisting of an oxygen atom and a sulfur nuclear atom (even if the heterocyclic group is substituted with alkyl) Any of the above compounds (1) to (5), or a salt thereof.
  • A is a 5- or 6-membered saturated heterocyclic group containing 1 to 2 oxygen atoms (the heterocyclic group may be substituted with alkyl, or;). ), A compound or a salt thereof.
  • A is a 5-membered heterocyclic group containing 1 to 2 oxygen atoms (the heterocyclic group is substituted with alkyl !, or;). Or a salt thereof.
  • A is a 5-membered heterocyclic group containing 2 oxygen atoms (the heterocyclic group is V, which may be substituted with alkyl; or).
  • a compound or a salt thereof is
  • R 3 , R 4 , R 5 The compound or a salt thereof according to any one of the above (1) to (17), wherein R 7 and R 8 are each a hydrogen atom or methyl.
  • R 3 , R 4 , R 5 The compound or a salt thereof according to any one of the above (1) to (17), wherein R 7 and R 8 are each a hydrogen atom.
  • (21) A method for controlling harmful plants by applying a herbicidally effective amount of any of the above-mentioned compounds (1) to (19) or a salt thereof.
  • reaction mixture was filtered, and the filtrate was washed with an aqueous solution of potassium carbonate, washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4.8 g of an enol ester.
  • Paddy soil was filled in 1 / 1,000,000 hectare pots, and seeds of Nobie and Firefly were sown and lightly covered with soil. Thereafter, the pool was allowed to stand still in a greenhouse at a waterlogging depth of 0.5 to Lcm, and the tuber of ⁇ rica ⁇ was planted the next day or two days later. Thereafter, the waterlogging depth was maintained at 3 to 4 cm. The water dilution was uniformly dropped with a pipette so as to have a predetermined amount of the active ingredient.
  • the mixture of the components (1) to (4) and the compound of the present invention are mixed at a weight ratio of 9: 1 to obtain a wettable powder.
  • a wettable powder is obtained by mixing the above components (1) to (4).
  • (1), (2) and (3) are mixed, passed through a pulverizer, (4) is added and kneaded, followed by extrusion granulation. The Thereafter, drying and sizing are performed to obtain a wettable powder.
  • Sopropol FL (trade name; made by Rhone Poulin) 2 parts by weight
  • IP Solvent 1620 (trade name; manufactured by Idemitsu Petrochemical Co., Ltd.) 32 parts by weight
  • the above components (1) to (6) are mixed and pulverized using a wet pulverizer (Dynomill) to obtain an aqueous suspension.
  • a wet pulverizer Dynomill
  • a novel triketone compound useful as an active ingredient of a herbicide, a method for producing the same, and a herbicide containing the same are provided.
  • the entire contents of the specification, claims, drawings, and abstract of Japanese Patent Application No. 2004-165472 filed on June 3, 2004 are cited here as a disclosure of the specification of the present invention. , Is to take in.

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Abstract

Divulgation de nouveaux composés de triketone, d’une méthode pour les produire, et d’un excellent herbicide les contenant. Plus particulièrement, divulgation d’un composé de triketone représenté par la formule (I) ci-dessous ou par ses sels. (I) Dans la formule, y est un intègre de 1-6 ; A représente un groupe hétérocyclique saturé de cinq ou six membres contenant 1 ou 2 atomes hétéro choisis dans le groupe et qui consistent en un atome d’oxygène et un atome de soufre, ou connexe. ; R1 représente un halogène ; R2 représente un alkyle, un haloalkyle ou un similaire ; R3, R4, R6, R7 and R8 représentent, respectivement, un atome d'hydrogène ou un alkyl ; R5 représente un atome d’hydrogène, un alkyl ou un cycloalkyl ; et Q représente un atome d’hydrogène ou un similaire.]
PCT/JP2005/010189 2004-06-03 2005-06-02 Composés de triketone, leur méthode de producion et celle d’herbicides les contenant Ceased WO2005118530A1 (fr)

Priority Applications (3)

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CN2005800178357A CN1960967B (zh) 2004-06-03 2005-06-02 三酮类化合物、其制造方法及含有该类化合物的除草剂
KR1020127028049A KR20120123735A (ko) 2004-06-03 2005-06-02 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는 제초제
KR1020067025326A KR101225441B1 (ko) 2004-06-03 2005-06-02 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는제초제

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JP2004165472 2004-06-03

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WO2012141277A1 (fr) 2011-04-14 2012-10-18 Ishihara Sangyo Kaisha, Ltd. Composition herbicide comprenant du flazasulfuron et de la métribuzine
WO2012141276A1 (fr) 2011-04-11 2012-10-18 Ishihara Sangyo Kaisha, Ltd. Composition herbicide comprenant du flazasulfuron et un inhibiteur de la protoporphyrinogène oxydase
WO2013133287A1 (fr) 2012-03-09 2013-09-12 石原産業株式会社 Composition herbicide
WO2014003202A1 (fr) 2012-06-29 2014-01-03 Ishihara Sangyo Kaisha, Ltd. Composition herbicide ayant une activité herbicide améliorée
WO2014208674A1 (fr) 2013-06-27 2014-12-31 石原産業株式会社 Composition herbicide avec sécurité améliorée pour les plantes
WO2022084334A1 (fr) * 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mélanges de pyrimidines servant de compositions herbicides
WO2022084335A1 (fr) * 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mélanges de pyridazines comme compositions herbicides
WO2023222834A1 (fr) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Compositions herbicides

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DK2848612T3 (da) * 2012-05-08 2017-11-06 Ishihara Sangyo Kaisha Fremgangsmåde til fremstilling af en substitueret benzoesyreforbindelse
TWI574622B (zh) * 2012-05-22 2017-03-21 Ishihara Sangyo Kaisha Herbicidal composition
CN110776410B (zh) * 2019-11-28 2020-08-21 东北农业大学 一种含肉桂酰基的三酮类化合物、制备方法及其应用

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WO2012141276A1 (fr) 2011-04-11 2012-10-18 Ishihara Sangyo Kaisha, Ltd. Composition herbicide comprenant du flazasulfuron et un inhibiteur de la protoporphyrinogène oxydase
WO2012141277A1 (fr) 2011-04-14 2012-10-18 Ishihara Sangyo Kaisha, Ltd. Composition herbicide comprenant du flazasulfuron et de la métribuzine
WO2013133287A1 (fr) 2012-03-09 2013-09-12 石原産業株式会社 Composition herbicide
WO2014003202A1 (fr) 2012-06-29 2014-01-03 Ishihara Sangyo Kaisha, Ltd. Composition herbicide ayant une activité herbicide améliorée
WO2014208674A1 (fr) 2013-06-27 2014-12-31 石原産業株式会社 Composition herbicide avec sécurité améliorée pour les plantes
WO2022084334A1 (fr) * 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mélanges de pyrimidines servant de compositions herbicides
WO2022084335A1 (fr) * 2020-10-19 2022-04-28 Syngenta Crop Protection Ag Mélanges de pyridazines comme compositions herbicides
JP2023545841A (ja) * 2020-10-19 2023-10-31 シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト 除草剤組成物としてのピリダジンの混合物
JP2023545842A (ja) * 2020-10-19 2023-10-31 シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト 除草剤組成物としてのピリミジンの混合物
WO2023222834A1 (fr) 2022-05-20 2023-11-23 Syngenta Crop Protection Ag Compositions herbicides

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