WO2014126070A1 - Triazinone carboxamide compound or salt thereof - Google Patents

Triazinone carboxamide compound or salt thereof Download PDF

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Publication number
WO2014126070A1
WO2014126070A1 PCT/JP2014/053098 JP2014053098W WO2014126070A1 WO 2014126070 A1 WO2014126070 A1 WO 2014126070A1 JP 2014053098 W JP2014053098 W JP 2014053098W WO 2014126070 A1 WO2014126070 A1 WO 2014126070A1
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Prior art keywords
alkyl
substituted
haloalkyl
cycloalkyl
phenyl
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PCT/JP2014/053098
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French (fr)
Japanese (ja)
Inventor
裕治 中村
大野　研
地 伏木田
寿彦 植木
中元　健一
冴香 小森
祐介 熊倉
久樹 田中
賢二 井櫻
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石原産業株式会社
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Publication of WO2014126070A1 publication Critical patent/WO2014126070A1/en

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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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • C07D417/14—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 three or more hetero rings

Definitions

  • the present invention relates to a novel triazinone carboxamide compound or salt thereof useful as an active ingredient of a herbicide, and a herbicide containing them.
  • Patent Document 1 Patent Document 2, Patent Document 3 and Patent Document 5 below disclose tetrazole- or triazole-arylcarboxamide derivatives having a certain structure.
  • Patent Document 4 discloses a 1,2,4-triazine-3,5-dione derivative having a certain structure. However, they do not disclose a triazinone carboxamide compound 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 triazinone carboxamide compound exhibits a high herbicidal effect on various weeds with a low dosage and yet exhibits high safety for various useful crops, thereby completing the present invention.
  • R 1 may be substituted by X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, heterocycle which may be substituted by X, it may be substituted with X benzyl, cyano C 1-6 alkyl, -C (O) R 5, -C (O) C 1 substituted by R 5 - 6 alkyl, -SO 2 -R 6, it is substituted with -SO 2 -R 6 6 alkyl or -Y-R 7 C 1 is substituted with - - 6 is alkyl C 1 was; R 2 is a hydrogen atom, C
  • the 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.
  • halogen atom or halogen as a substituent in the general formula (I) examples include fluorine, chlorine, bromine or 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.
  • a branched C 1 -C 6 group may be mentioned.
  • 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 And straight-chain 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 8 groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
  • heterocycle in the general formula (I) examples include C2-C10 heterocycles having one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom.
  • groups such as sole, benzothiazole, benzimidazole, isoxazole, isoxazoline, oxazole, oxazoline, isothiazole, isothiazoline, thiazole, tetrahydrofuran, thiomorpholine or thiazoline. .
  • “may be substituted with X” may be any substitution position when substituted with X, and the number of X may be 1 or 2 or more. When is 2 or more, X represents the same or different.
  • the substitution position of alkyl, cycloalkyl, alkoxy, cyano, —C (O) R 5 , —SO 2 —R 6 , —YR 7 as the secondary substituent in general formula (I) is any The substitution position may be used.
  • the R 1 substituent position in the alkoxy moiety of the "C 1 - - 6 alkoxy C 1 6 alkyl” may be any substitution position.
  • the substitution number of the secondary substituent may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different.
  • the salt of the compound of the general formula (I) includes any agriculturally acceptable salt, for example, alkali metal salts such as sodium salt and potassium salt; Alkaline earth metal salts; amine salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates Etc.
  • alkali metal salts such as sodium salt and potassium salt
  • Alkaline earth metal salts such as dimethylamine salts and triethylamine salts
  • inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates
  • organic acid salts such as acetates and methanesulfonates Etc.
  • the present invention includes both each isomer and isomer mixture.
  • 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.
  • the 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, but is limited to these methods. It is not a thing.
  • R 2-a is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted with X, which may be benzyl substituted by X, cyano C 1-6 alkyl, - (CR a R b ) n —C (O) R 5 , — (CR a R b ) n —SO 2 —R 6 or — (CR a R b ) n —Y—R 7 , R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R a , R b , A, X,
  • the above reaction can be carried out in the presence of a solvent.
  • a solvent Any solvent may be used as long as it is inert to the reaction.
  • 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), dimethyl sulfoxide (DMSO), N, N-dimethylacetamide (DMA) , Aprotic polar solvents such as hexamethylphosphoric triamide (HMPA), sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxan
  • the above reaction can be carried out 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; 2,6-lutidine; and the like.
  • Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium methoxide, sodium ethoxide, One or more kinds of alkali metal alkoxides such as potassium tertiary butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; and the like can be appropriately selected and mixed for use.
  • 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
  • the above reaction can be performed in the presence of a palladium catalyst, if necessary.
  • a palladium catalyst for example, Pd 2 (dba) 3 , Pd (PPh 3 ) 4, Pd (dppf) 2 Cl 2, Pd (OAc) 2 and the like can be mentioned, which can be carried out in the presence of a ligand as necessary.
  • the ligand include triphenylphosphine, tricyclohexylphosphine, tritertiary butylphosphine and the like.
  • the above reaction can be carried out in the presence of, for example, lithium chloride, cesium fluoride, copper iodide or the like, if necessary.
  • the above reaction can be carried out in the presence of a phase transfer catalyst, if necessary.
  • phase transfer catalyst examples include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown-6-ether;
  • quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown-6-ether;
  • the above reaction can be carried out in the presence of a catalyst such as potassium iodide, if necessary.
  • the reaction temperature for the above reaction is usually from 0 ° C to 200 ° C, and the reaction time is usually from 1 minute to 48 hours.
  • the compound represented by the formula (II) can be synthesized according to the method described in WO2012 / 002096.
  • the compound represented by the formula (III) can be synthesized according to a commercially available compound or a method described in WO2013 / 0175559 or ORGANIC LETTERS 2000, 20, 3237-3240. Production method [2-1] and Production method [2-2]
  • the above reaction can be carried out in the presence of a solvent.
  • a solvent the same thing as the said manufacturing method 1 etc. are mentioned, These 1 type (s) or 2 or more types can be selected suitably.
  • the above reaction can be carried out in the presence of a condensing agent as necessary.
  • the condensing agent include dicyclohexylcarbodiimide (DCC), N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide (EDC or WSC), N, N-carbonyldiimidazole (CDI), and the like.
  • DCC dicyclohexylcarbodiimide
  • EDC or WSC N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide
  • CDI N-carbonyldiimidazole
  • the above reaction can be carried out in the presence of a base as necessary. Examples of the base include those similar to those in Production Method 1, and
  • the above reaction can be carried out in the presence of a solvent.
  • the solvent include those similar to those in Production Method 1, and one or more of these can be appropriately selected and mixed for use.
  • the above reaction can be carried out in the presence of a halogenating agent.
  • the halogenating agent include oxalyl chloride and thionyl chloride.
  • the reaction temperature for the above reaction is usually from 0 ° C to 200 ° C, and the reaction time is usually from 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.
  • barnyardgrass or barnyardgrass barnyardgrass (Echinochloa crus-galli L. , Echinochloa oryzicola vasing.)
  • Crabgrass crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.)
  • Green foxtail Setaria viridis L.
  • Akino foxtail Setaria faberi Herrm.
  • Yellow foxtail Setaria lutescens Hubb.
  • Goosegrass Eleusine indica ) .
  • Oats wild oat ( Avena fatua L.)
  • sorghum sorghum johnsongrass ( Sorghum halepense L.)
  • shibamugi quack
  • weed grasses such as; Cyperus Iria (rice flatsedge (Cyperus iria L.) ), purple nutsedge (purple nutsedge (Cyperus rotundus L.) ), yellow nutsedge (yellow nutsedge (Cyperus esculentus L.) ), bulrush (Japanese bulrush ( Scirpus juncoides )), Japanese squirrel (flatsedge ( Cyperus serotinus )), Japanese cypress (small-flower umbrellaplant ( Cyperus difformis )), Japanese pine (slender spikerush ( Eleocharis) acicularis)), water chestnut (water chestnut (Eleocharis kuroguwai)) Cyperaceae weeds (cyperaceae) such as; arrowhead (Japanese ribbon waparo (Sagittaria
  • Amaranthaceae weeds such as (amaranthaceae); Sanaetade (pale smartweed (Polygonum lapathifolium L.) ), Harutade (ladysthumb (Polygonum persicaria L .)), Buckwheat (wild buckwheat ( Polygonum convolvulus L.)), weeping ( Polygonum aviculare L.)), weeds (polygonafinale); radish (flexuous bittercress ( Cardamine flexuosa WITH.)), crabiferae (cruciferae) such as shepherd's-purse ( Capsella bursapastoris Medik.) and Indian mustard ( Brassica juncea Czern.); tall morningglory ( Ipomoea purpurea L.), convolvulus bindweed ( Convolvulus arvensis L.)), convolvulaceae like common morning glory (ivyleaf morningglory ( Ipomoea
  • useful crops such as corn (corn ( Zea mays L.)), soybean (soybean ( Glycine max Merr.)), Cotton (cotton ( Gossypium spp.)), Wheat (wheat ( Triticum spp.)), Rice ( rice ( Oryza sativa L.)), barley (barley ( Hordeum Vulgare L.)), rye (rye ( Secalecereale L.)), oat (oat ( Avena sativa L.)), sorghum (sorgo ( Sorghum bicolor Moench)) Rape , Brassica napus L., sunflower ( Helianthus annuus L.), sugar beet ( Beta Vulgaris L.), sugar cane (suger cane ( Saccharum officinarum L.)), turf lawngrass ( Zoysia japonica stend )), peanuts (peanut ( Arachis hypogae a L.)), flax (flax (
  • 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. In general, it is applied so that the compound according to the present invention is 0.1 to 5,000 g, preferably 0.5 to 3,000 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-described 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 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, and pyrazole photole.
  • Pyrazole compounds such as (pyrasulfotole); others, amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione (Mesotrione), tembotrione, tefuryltrione, fenquinotrione, cyclopyrimorate, isoxaflutole, difenzo coat ( difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, bicyclopyron, picolinafen, biflubutamide, ketospiradox ( Ketospiradox), ketospiradox-potassium, compounds described
  • 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), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid ), Dimethylarso Dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC , Ferrous sulfate (flurus ⁇ ⁇ sulf
  • Xanthomonas campestris Xanthomonas campestris
  • epi heart Sils Nematosorusu Epicoccosirus nematosorus
  • epi heart Sils Nematosuperasu Epicoccosirus nematosperus
  • Ekiserohiramu monoceras Exserohilum monoseras
  • parasitic plants such as Drechslera monoceras (Drechsrela monoceras) It is supposed to show herbicidal efficacy by doing.
  • Preferred embodiments of the compound according to the present invention include the following. (1) the formula (I), phenyl R 1 is optionally substituted with X, C 1 - 6 alkyl or C 1 - 6 alkoxy C 1 - 6 is alkyl; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, optionally substituted with X benzyl, cyano C 1-6 alkyl, - (CR a R b) n -C (O) R 5, - ( CR a R b) n -SO 2 -R 6 or - (CR a R b) be n -Y-R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 1 - 6 haloalkyl, C 3 - 6 cycloalkyl C 1 - 6 alkyl, phen
  • R 1 is optionally substituted with X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl or C 1 - 6 haloalkyl;
  • R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted with X, which may be benzyl substituted by X, cyano C 1-6 alkyl, -(CR a R b ) n -C (O) R 5 ,-(CR a
  • Synthesis example 4 4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-1,2,4-triazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro- Synthesis of 1,2,4-triazine-6-carboxamide (Compound No. 2-23) 4- (2-Chlorophenyl) -2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1 , 2,4-Triazine-6-carboxylic acid (287 mg) and chloroform (2 ml) were stirred, and oxalyl chloride (170 ⁇ l) and DMF (1 drop) were added thereto at room temperature for 2 hours. Stir.
  • Tables 1 to 3 typical examples of the compounds according to the present invention are listed in Tables 1 to 3. These compounds can be synthesized based on the above synthesis examples or the various production methods described above.
  • Tables 1 to 3 the numerical values described in the physical properties column indicate melting points (° C.), and for compounds described as NMR, their 1 H-NMR spectral data are listed in Table 4.
  • No. represents 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
  • 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
  • n-Hex is a normal hexyl group
  • Np is a neopentyl group
  • c-Pr is a cyclopropyl group
  • c-Bu is a cyclobutyl group.
  • C-Pen represents a cyclopentyl group
  • c-Hex represents a cyclohexyl group
  • c-Hep represents a cycloheptyl group
  • c-Oct represents a cyclooctyl group
  • Ph represents a phenyl group
  • Bn represents a benzyl group.
  • (3-CF 3 ) Ph represents a phenyl group substituted with CF 3 at the 3-position
  • (2,3-Cl 2 ) Ph represents a phenyl group substituted with Cl at the 2-position and the 3-position
  • (2 -Cl-6-CF 3 ) Ph represents a phenyl group substituted with Cl at the 2-position and CF 3 at the 6-position
  • (2-Cl) Bn represents a benzyl group substituted with Cl at the 2-position of the benzene ring
  • other similar descriptions are based on this.
  • Test example 1 A field crop soil was filled 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) barbyard (crabgrass ( Digitaria sanguinalis L.)); 0.5-3.0 leaf stage (3) Green foxtail ( Setaria viridis L.); 1.5-3.5 leaf stage; (4) Red root pigweed ( Amaranthus retroflexus L.); 0.2-2.5 leaf stage; (5) American goldfish ( prickly sida ( Sida spinosa L.)); cotyledon to 2.0 leaves, (6) velvetleaf ( Abutilon theophrasti MEDIC.); 0.2 to 2.0 leaves, (7) rice (rice ( Oryza sativa L.)); 1.0 to 2.5 leaf stage, (8) corn (corn ( Zea mays L.)); 2.0 to 3.5 leaf stage, (9) wheat (wheat ( Triticum
  • Test example 2 1 / 170,000 hectare pot filled with upland soil, various plants (barnyardgrass ( Echinochloa crus-galli L.)), barkyard (crabgrass ( Digitaria sanguinalis L.)), green foxtail (green foxtail ( Setaria viridis L.)), Red root pigweed ( Amaranthus retroflexus L.), American deer (prickly sida ( Sida spinosa L.)), green velvetleaf ( Abutilon theophrasti MEDIC.), Rice (rice ( oryza sativa L.)), maize ( Corn ( Zea mays L.)), wheat (wheat ( Triticum spp.)), cotton (cotton ( Gossypium spp.)), soybean (soybean ( Glycine max Merr.))) were sown.
  • a wettable powder or emulsion prepared according to the usual formulation method of the compound according to the present invention is weighed so as to have a predetermined active ingredient amount, diluted in water equivalent to 500 liters per hectare, and a small spray Soil treatment.
  • the state of growth of various plants was observed with the naked eye, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed).
  • the results shown in Table 6 were obtained.
  • Test example 3 Paddy soil was packed in a 1 / 1,000,000 hectare pot, and seeds of barnyardgrass ( Echinochloa oryzicola vasing.) And firefly (Japanese bulrush ( Scirpus juncoides )) were sown and lightly covered with soil. Thereafter, the tube 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.
  • 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 The components (1) to (4) are put into a high-speed mixing fine granulator, 20% by weight of 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) Calcium lignin sulfonate 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. Then, a granule 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 Rhône-Poulenc) 2 parts by weight (3) Solpol 355 (trade name; manufactured by Toho Chemical 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 entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2013-028453 filed on February 15, 2013 are incorporated herein as the disclosure of the specification of the present invention. Is.

Abstract

Provided is a novel herbicide having a significant herbicidal activity on undesirable plants. A compound represented by general formula (I) [wherein R1 represents a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-6 cycloalkyl group, a C1-6 haloalkyl group or the like; R2 represents a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-6 cycloalkyl group, a C1-6 haloalkyl group, a C2-6 haloalkenyl group, a C2-6 haloalkynyl group, a C3-6 halocycloalkyl group or the like; R3 represents a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-6 cycloalkyl group, a C1-6 haloalkyl group or the like; and R4 represents a hydrogen atom, a C1-6 alkyl group, a C2-6 alkenyl group, a C2-6 alkynyl group, a C3-8 cycloalkyl group, a C1-6 haloalkyl group, a C2-6 haloalkenyl group or the like] or a salt thereof.

Description

トリアジノンカルボキサミド系化合物又はその塩Triazinone carboxamide compound or salt thereof
　本発明は、除草剤の有効成分として有用な新規のトリアジノンカルボキサミド系化合物又はその塩、並びにそれらを含有する除草剤に関する。 The present invention relates to a novel triazinone carboxamide compound or salt thereof useful as an active ingredient of a herbicide, and a herbicide containing them.
　下記特許文献１、特許文献２、特許文献３及び特許文献５には、一定の構造を有するテトラゾール－又はトリアゾール－アリールカルボキサミド誘導体が開示されている。また、特許文献４には、一定の構造を有する１，２，４－トリアジン－３，５－ジオン誘導体が開示されている。しかしながら、それらには後述する一般式（Ｉ）で表されるトリアジノンカルボキサミド系化合物は開示されていない。 Patent Document 1, Patent Document 2, Patent Document 3 and Patent Document 5 below disclose tetrazole- or triazole-arylcarboxamide derivatives having a certain structure. Patent Document 4 discloses a 1,2,4-triazine-3,5-dione derivative having a certain structure. However, they do not disclose a triazinone carboxamide compound represented by the general formula (I) described later.
国際公開公報ＷＯ２０１２／０２８５７９号International Publication No. WO2012 / 028579 国際公開公報ＷＯ２０１２／１２３４０９号International Publication No. WO2012 / 123409 国際公開公報ＷＯ２０１２／１３０６８５号International Publication No. WO2012 / 130685 国際公開公報ＷＯ２０１２／００２０９６号International Publication No. WO2012 / 002096 国際公開公報ＷＯ２０１３／０８７５７７号International Publication No. WO2013 / 087577
　従来から、雑草を防除する作業の省力化や農園芸用作物の生産性向上を図る為、雑草に対して優れた除草性能を有し、且つ栽培作物に対する安全性を有する除草剤が所望されている。これからの新しい除草剤の開発においては、その施用薬量を低く抑えつつも所望の除草効果を発揮することができる化合物の創出が希求されている。また、実用的な残効性を示しつつも必要以上に土壌中に残留したり、雨水などにより施用箇所以外の土壌へ有効成分が流出するなどして環境へ悪影響を及ぼしたりする恐れの少ない化合物の創出が希求されている。さらには、高い動物安全性を備えた化合物の創出が望まれている。しかし、そのような目的に適した新規化合物の探索は試行錯誤に頼っている。 Conventionally, there has been a demand for a herbicide that has excellent herbicidal performance against weeds and safety for cultivated crops in order to save labor in controlling weeds and improve productivity of agricultural and horticultural crops. Yes. In the development of new herbicides in the future, there is a demand for the creation of compounds that can exhibit the desired herbicidal effect while keeping the amount of applied herbage low. In addition, compounds that have practical residual effects but are less likely to remain in the soil than necessary or have a negative impact on the environment due to the outflow of active ingredients to soils other than the application site due to rainwater, etc. Creation of is demanded. Furthermore, creation of a compound with high animal safety is desired. However, the search for new compounds suitable for such purposes relies on trial and error.
　本発明者らは、前記課題を解決するような、より優れた除草剤を見出すべく種々検討した。その結果、新規なトリアジノンカルボキサミド系化合物が、低薬量で多様な雑草に高い除草効果を示し、尚且つ各種有用作物に高い安全性を示すことを見出し、本発明を完成した。 The present inventors have made various studies in order to find a more excellent herbicide that can solve the above-mentioned problems. As a result, the present inventors have found that the novel triazinone carboxamide compound exhibits a high herbicidal effect on various weeds with a low dosage and yet exhibits high safety for various useful crops, thereby completing the present invention.
　即ち本発明は、下記（１）、（２）及び（３）を要旨とするものである。
（１）一般式（Ｉ）： That is, the gist of the present invention is the following (1), (2) and (3).
(1) General formula (I):
Figure JPOXMLDOC01-appb-C000002
 〔式（Ｉ）中、Ｒ１はＸで置換されてもよいフェニル、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－Ｃ(Ｏ)Ｒ５、－Ｃ(Ｏ)Ｒ５で置換されたＣ１‐６アルキル、－ＳＯ２－Ｒ６、－ＳＯ２－Ｒ６で置換されたＣ１‐６アルキル又は－Ｙ－Ｒ７で置換されたＣ１‐６アルキルであり；Ｒ２は水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３はＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ３‐６シクロアルキルＣ１‐６アルキル、Ｘで置換されてもよいフェニル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ４は水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ１‐６アルキルＣ３‐８シクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環又はジＣ１‐６アルキルアミノであり；Ｒ７はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル、Ｃ１‐６アルコキシカルボニル又はＣ３‐６シクロアルキルオキシカルボニルであり；ＡはＣＨ又は窒素原子であり；Ｒａ及びＲｂはそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘはハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルフィニル、Ｃ１‐６アルキルスルホニル、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６ハロアルキルチオ、Ｃ１‐６ハロアルキルスルフィニル、Ｃ１‐６ハロアルキルスルホニル、ニトロ、シアノ又はフェニルであり；Ｙは酸素原子又は硫黄原子であり；Ｗ１は酸素原子又は硫黄原子であり；Ｗ２は酸素原子又は硫黄原子であり；ｎは０、１又は２である〕で表される化合物又はその塩、
（２）（１）に記載の化合物又はその塩を有効成分として含有する除草剤、
（３）（１）に記載の化合物又はその塩の除草有効量を望ましくない植物又はそれが生育する場所に施用し、望ましくない植物を防除又はその生育を抑制する方法。
Figure JPOXMLDOC01-appb-C000002
 [In formula (I), R 1 may be substituted by X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, heterocycle which may be substituted by X, it may be substituted with X benzyl, cyano C 1-6 alkyl, -C (O) R 5, -C (O) C 1 substituted by R 5 - 6 alkyl, -SO 2 -R 6, it is substituted with -SO 2 -R 6 6 alkyl or -Y-R 7 C 1 is substituted with - - 6 is alkyl C 1 was; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 C Alkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted by X, it may be substituted with X Benzyl, cyano C 1-6 alkyl, — (CR a R b ) n —C (O) R 5 , — (CR a R b ) n —SO 2 —R 6 or — (CR a R b ) n —Y It is a -R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 3 - 6 cycloalkyl C 1 - 6 be 6 cycloalkylalkyl, is also phenyl or C 1 substituted with X - - 6 alkoxy C 1; R 4 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl , C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 1 - 6 alkyl C 3 - 8 cycloalkyl, phenyl optionally substituted by X, naphthyl which may be substituted by X, optionally substituted with X good heterocycle, -CH 2 benzyl optionally substituted or X -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, optionally substituted with X phenyl , which may be substituted by X phenoxy, heterocycle which may be substituted with X, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - 6 alkoxy C 1 - 6 alkyl by and; R 6 is C 1 - 6 alkyl, C 1 - Ah 6 alkylamino - 6 haloalkyl, phenyl optionally substituted by X, which may heterocycle or be di C 1 substituted with X Ri; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, which may be substituted by X phenyl, C 1 - 6 alkylcarbonyl, C 1 - 6 alkoxycarbonyl or C 3 - it is a 6 cycloalkyloxycarbonyl; A is CH or a nitrogen atom; R a and R b are each independently a hydrogen atom or a C 1 - be 6 alkyl; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 alkylthio, C 1 - 6 alkylsulfinyl, C 1 - 6 alkylsulfonyl, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 haloalkylthio, C 1 - 6 haloalkylsulfinyl, 1 - 6 haloalkylsulfonyl, nitro, cyano or phenyl; Y is oxygen atom or sulfur atom; W 1 is oxygen atom or sulfur atom; W 2 is oxygen atom or sulfur atom; n is 0, Or a salt thereof,
(2) a herbicide containing the compound or salt thereof according to (1) as an active ingredient,
(3) A method for controlling or inhibiting the growth of an undesirable plant by applying a herbicidally effective amount of the compound or salt thereof according to (1) to an undesirable plant or a place where it grows.
　前記一般式（Ｉ）の化合物又はその塩は、類似する従来化合物に比して望ましくない植物（雑草）への著しい除草活性の向上を実現する。 The 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.
　一般式（Ｉ）中のハロゲン原子又は置換基としてのハロゲンとしては、フッ素、塩素、臭素又はヨウ素の各原子が挙げられる。置換基としてのハロゲン原子の数は１又は２以上であってよく、２以上の場合、各ハロゲン原子は同一でも相異なってもよい。また、ハロゲン原子の置換位置は何れの位置でもよい。 Examples of the halogen atom or halogen as a substituent in the general formula (I) include fluorine, chlorine, bromine or iodine atoms. The number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
　一般式（Ｉ）中のアルキル又はアルキル部分としては、例えば、メチル、エチル、ノルマルプロピル、イソプロピル、ノルマルブチル、イソブチル、セカンダリーブチル、ターシャリーブチル、ノルマルペンチル、ネオペンチル、ノルマルヘキシルのような直鎖又は分岐鎖状のC１－C６の基が挙げられる。 Examples of the alkyl or alkyl moiety in the general formula (I) include a straight chain such as methyl, ethyl, normal propyl, isopropyl, normal butyl, isobutyl, secondary butyl, tertiary butyl, normal pentyl, neopentyl, and normal hexyl. A branched C 1 -C 6 group may be mentioned.
　一般式（I）中のアルケニル又はアルケニル部分としては、例えば、ビニル、１－プロペニル、２－プロペニル、イソプロペニル、２－メチル－１－プロペニル、１－メチル－１－プロペニル、２－メチル－２－プロペニル、１－メチル－２－プロペニル、１－ブテニル、２－ブテニル、３－ブテニル、１－ペンテニル、２－ペンテニル、２－メチル－２－ブテニル、１－ヘキセニル、２,３－ジメチル－２－ブテニルのような直鎖又は分岐鎖状のC２－C６の基が挙げられる。 Examples of the alkenyl or alkenyl moiety in the general formula (I) include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl and 2-methyl-2. -Propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 1-hexenyl, 2,3-dimethyl-2 And straight-chain or branched C 2 -C 6 groups such as butenyl.
　一般式（I）中のアルキニル又はアルキニル部分としては、例えば、エチニル、１－プロピニル、２－プロピニル、１－ブチニル、２－ブチニル、３－ブチニル、１－メチル－２－プロピニル、２－メチル－３－ブチニル、１－ヘキシニル、２－ヘキシニル、３－ヘキシニル、４－ヘキシニル、５－ヘキシニルのような直鎖又は分岐鎖状のC２－C６の基が挙げられる。 Examples of the alkynyl or alkynyl moiety in the general formula (I) include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl- Examples thereof include linear or branched C 2 -C 6 groups such as 3-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl.
　一般式（I）中のシクロアルキル又はシクロアルキル部分としては、例えば、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチルのようなC３－C８の基が挙げられる。 Examples of the cycloalkyl or cycloalkyl moiety in the general formula (I) include C 3 -C 8 groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl.
　一般式（I）中のヘテロ環としては、酸素原子、硫黄原子及び窒素原子からなる群より選択される同一又は異なった１個以上のヘテロ原子を有する炭素数２～１０のヘテロ環が挙げられ、特に限定しない限り、例えばオキシラン、フラン、チオフェン、ピロール、ピラゾール、イミダゾール、トリアゾール、ピリジン、ピリミジン、ピラジン、ピリダジン、ピロリジン、ピペリジン、ピペラジン、モルホリン、ベンゾフラン、ベンゾチオフェン、インドール、ベンゾオキサゾール、ベンゾジオキソール、ベンゾチアゾール、ベンズイミダゾール、イソオキサゾール、イソオキサゾリン、オキサゾール、オキサゾリン、イソチアゾール、イソチアゾリン、チアゾール、テトラヒドロフラン、チオモルホリン又はチアゾリンなどの基が挙げられる。 Examples of the heterocycle in the general formula (I) include C2-C10 heterocycles having one or more heteroatoms selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom. Unless otherwise specified, for example, oxirane, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, pyridine, pyrimidine, pyrazine, pyridazine, pyrrolidine, piperidine, piperazine, morpholine, benzofuran, benzothiophene, indole, benzoxazole, benzodioxide And groups such as sole, benzothiazole, benzimidazole, isoxazole, isoxazoline, oxazole, oxazoline, isothiazole, isothiazoline, thiazole, tetrahydrofuran, thiomorpholine or thiazoline. .
　一般式（I）中の「Ｘで置換されてもよい」とは、Ｘで置換される場合は何れの置換位置でもよく、Ｘの数は１又は２以上であってもよく、Ｘの数が２以上の場合は、Ｘは同一であっても異なっていてもよいことを表す。
　また、一般式（I）中の二次置換基としてのアルキル、シクロアルキル、アルコキシ、シアノ、－Ｃ(Ｏ)Ｒ５、－ＳＯ２－Ｒ６、－Ｙ－Ｒ７の置換位置は、何れの置換位置でもよい。例えばＲ１の「Ｃ１‐６アルコキシＣ１‐６アルキル」のアルコキシ部分の置換位置は、何れの置換位置でもよい。二次置換基の置換数は１又は２以上であってもよく、２以上の場合、それらは同一であっても異なっていてもよい。 In the general formula (I), “may be substituted with X” may be any substitution position when substituted with X, and the number of X may be 1 or 2 or more. When is 2 or more, X represents the same or different.
In addition, the substitution position of alkyl, cycloalkyl, alkoxy, cyano, —C (O) R 5 , —SO 2 —R 6 , —YR 7 as the secondary substituent in general formula (I) is any The substitution position may be used. For example the R 1 substituent position in the alkoxy moiety of the "C 1 - - 6 alkoxy C 1 6 alkyl" may be any substitution position. The substitution number of the secondary substituent may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different.
　一般式（I）の化合物の塩としては、農業上許容されるものであればあらゆる塩が含まれるが、例えば、ナトリウム塩、カリウム塩のようなアルカリ金属塩；マグネシウム塩、カルシウム塩のようなアルカリ土類金属塩；ジメチルアミン塩、トリエチルアミン塩のようなアミン塩；塩酸塩、過塩素酸塩、硫酸塩、硝酸塩のような無機酸塩；酢酸塩、メタンスルホン酸塩のような有機酸塩などが挙げられる。 The salt of the compound of the general formula (I) includes any agriculturally acceptable salt, for example, alkali metal salts such as sodium salt and potassium salt; Alkaline earth metal salts; amine salts such as dimethylamine salts and triethylamine salts; inorganic acid salts such as hydrochlorides, perchlorates, sulfates and nitrates; organic acid salts such as acetates and methanesulfonates Etc.
　一般式（I）の化合物には、光学異性体のような異性体が存在する場合があるが、本発明には各異性体及び異性体混合物の双方が含まれる。本願明細書においては、特に言及しない限り、異性体は混合物として記載する。尚、本発明には、当該技術分野における技術常識の範囲内において、前記異性体以外の各種異性体も含まれる。また、異性体の種類によっては、前記一般式（I）とは異なる化学構造となる場合があるが、当業者であればそれらが異性体の関係にあることが十分認識できる為、本発明の範囲内であることは明らかである。 In the compound of the general formula (I), there may be an isomer such as an optical isomer, but the present invention includes both each isomer and isomer mixture. In the present specification, unless otherwise specified, isomers are described as a mixture. The present invention includes various isomers other than the isomers within the scope of common technical knowledge in the technical field. In addition, depending on the type of isomer, there may be a chemical structure different from that of the general formula (I). However, since those skilled in the art can sufficiently recognize that they are related to isomers, Obviously, it is within range.
　一般式（I）の化合物又はその塩（以下、本発明に係る化合物と略す）は、以下の製造方法、並びに通常の塩の製造方法に従って製造することができるが、これらの方法に限定されるものではない。 The 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, but is limited to these methods. It is not a thing.
　製法〔１〕 Manufacturing method [1]
Figure JPOXMLDOC01-appb-C000003
 （式中、Ｒ２-aはＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり、Ｒ１、Ｒ３、Ｒ４、Ｒ５、Ｒ６、Ｒ７、Ｒａ、Ｒｂ、Ａ、Ｘ、Ｙ、W１、W２及びｎは前述の通りであり、Ｌはハロゲン原子などの脱離基を示す。）
　上記反応は、溶媒の存在下に行うことができる。溶媒としては反応に不活性な溶媒であればいずれのものでもよく、例えば、塩化メチレン、クロロホルム、ジクロロエタン、トリクロロエタン、四塩化炭素のようなハロゲン化炭化水素類；ベンゼン、トルエン、キシレン、ニトロベンゼン、クロロベンゼンのような芳香族炭化水素類；酢酸メチル、酢酸エチル、酢酸プロピルのようなエステル類；アセトニトリル、N,N－ジメチルホルムアミド（DMF）、ジメチルスルホキシド（DMSO）、N,N－ジメチルアセトアミド(DMA)、ヘキサメチルリン酸トリアミド（HMPA）、スルホランのような非プロトン性極性溶媒；ジエチルエーテル、ターシャリーブチルメチルエーテル、１,４-ジオキサン、テトラヒドロフラン(THF)、1,2-ジメトキシエタンのようなエーテル類；などから１種又は２種以上を適宜選択することができる。
　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、有機塩基でも無機塩基でもいずれでもよい。有機塩基としては、例えば、トリエチルアミン、ジイソプロピルエチルアミンのような第三級アミン類；1,8-ジアザビシクロ[5,4,0]-7-ウンデセン（DBU）；ピリジン；4-(ジメチルアミノ)ピリジン；2,6-ルチジン；などが挙げられる。無機塩基としては、例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウムのようなアルカリ金属炭酸塩；炭酸水素ナトリウム、炭酸水素カリウムのようなアルカリ金属炭酸水素塩；炭酸カルシウム、炭酸バリウムのようなアルカリ土類金属炭酸塩；水酸化リチウム、水酸化ナトリウム、水酸化カリウムのようなアルカリ金属水酸化物；水酸化カルシウム、水酸化バリウムのようなアルカリ土類金属水酸化物；ナトリウムメトキシド、ナトリウムエトキシド、カリウムターシャリーブトキシドなどのアルカリ金属アルコキシド類；ナトリウムヒドリド、カリウムヒドリドなどのアルカリ金属ヒドリド類；などから１種又は２種以上を適宜選択、混合して使用することができる。
　上記反応は、必要に応じてパラジウム触媒存在下に行うことができる。例えば、Pd2(dba)3、Pd(PPh3)4、Pd(dppf)2Cl2、Pd(OAc)2などが挙げられ、必要に応じて配位子の存在下に行うことができる。配位子としては、例えば、トリフェニルホスフィン、トリシクロヘキシルホスフィン、トリターシャリーブチルホスフィンなどが挙げられる。
　上記反応は必要に応じて、例えば塩化リチウム、フッ化セシウム、ヨウ化銅などの存在下に行うことができる。
　上記反応は、必要に応じて相関移動触媒の存在下に行うことができる。相関移動触媒としては、例えば、テトラノルマルブチルアンモニウムブロミド、ベンジルトリエチルアンモニウムブロミドのような四級アンモニウム塩；18-クラウン-6-エーテル；などが挙げられる。
　上記反応は、必要に応じてヨウ化カリウムのような触媒の存在下に行うことができる。
　上記反応の反応温度は、通常０℃～２００℃、反応時間は、通常１分～４８時間で行うことができる。
Figure JPOXMLDOC01-appb-C000003
 (Wherein, R 2-a is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted with X, which may be benzyl substituted by X, cyano C 1-6 alkyl, - (CR a R b ) n —C (O) R 5 , — (CR a R b ) n —SO 2 —R 6 or — (CR a R b ) n —Y—R 7 , R 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R a , R b , A, X, Y, W 1 , W 2 and n are as described above, and L represents a leaving group such as a halogen atom. )
The above reaction can be carried out in the presence of a solvent. Any solvent may be used as long as it is inert to the reaction. For example, halogenated hydrocarbons such as methylene chloride, chloroform, dichloroethane, trichloroethane, 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), dimethyl sulfoxide (DMSO), N, N-dimethylacetamide (DMA) , Aprotic polar solvents such as hexamethylphosphoric triamide (HMPA), sulfolane; ethers such as diethyl ether, tertiary butyl methyl ether, 1,4-dioxane, tetrahydrofuran (THF), 1,2-dimethoxyethane 1 type or 2 types or more are appropriately selected from Can.
The above reaction can be carried out in the presence of a base as necessary. The base may be either an organic base or an inorganic base. Examples of the organic base include tertiary amines such as triethylamine and diisopropylethylamine; 1,8-diazabicyclo [5,4,0] -7-undecene (DBU); pyridine; 4- (dimethylamino) pyridine; 2,6-lutidine; and the like. Examples of the inorganic base include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkaline earth metals such as calcium carbonate and barium carbonate Metal carbonates; alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide; alkaline earth metal hydroxides such as calcium hydroxide and barium hydroxide; sodium methoxide, sodium ethoxide, One or more kinds of alkali metal alkoxides such as potassium tertiary butoxide; alkali metal hydrides such as sodium hydride and potassium hydride; and the like can be appropriately selected and mixed for use.
The above reaction can be performed in the presence of a palladium catalyst, if necessary. For example, Pd 2 (dba) 3 , Pd (PPh 3 ) 4, Pd (dppf) 2 Cl 2, Pd (OAc) 2 and the like can be mentioned, which can be carried out in the presence of a ligand as necessary. Examples of the ligand include triphenylphosphine, tricyclohexylphosphine, tritertiary butylphosphine and the like.
The above reaction can be carried out in the presence of, for example, lithium chloride, cesium fluoride, copper iodide or the like, if necessary.
The above reaction can be carried out in the presence of a phase transfer catalyst, if necessary. Examples of the phase transfer catalyst include quaternary ammonium salts such as tetranormal butyl ammonium bromide and benzyl triethyl ammonium bromide; 18-crown-6-ether;
The above reaction can be carried out in the presence of a catalyst such as potassium iodide, if necessary.
The reaction temperature for the above reaction is usually from 0 ° C to 200 ° C, and the reaction time is usually from 1 minute to 48 hours.
　製法〔２〕 Manufacturing method [2]
Figure JPOXMLDOC01-appb-C000004
Figure JPOXMLDOC01-appb-C000004
（式中、Ｒ１、Ｒ３、Ｒ４、Ａ、W１、W２及びＬは前述の通りである。）
　式（ＩＩ）で表される化合物はＷＯ２０１２／００２０９６に記載の方法に準じて合成できる。式（ＩＩＩ）で表される化合物は市販の化合物あるいはWO２０１３／０１７５５９又はORGANIC LETTERS 2000, 20, 3237-3240に記載される方法に準じて合成できる。
　製法〔２－１〕及び製法〔２－２〕 (In the formula, R 1 , R 3 , R 4 , A, W 1 , W 2 and L are as described above.)
The compound represented by the formula (II) can be synthesized according to the method described in WO2012 / 002096. The compound represented by the formula (III) can be synthesized according to a commercially available compound or a method described in WO2013 / 0175559 or ORGANIC LETTERS 2000, 20, 3237-3240.
Production method [2-1] and Production method [2-2]
　上記反応は、溶媒の存在下に行うことができる。溶媒としては、前記製法１と同様のものなどが挙げられ、これらの１種又は２種以上を適宜選択することができる。
　上記反応は、必要に応じて縮合剤の存在下に行うことができる。縮合剤としては、ジシクロヘキシルカルボジイミド（DCC）、Ｎ－(３－ジメチルアミノプロピル)－Ｎ’-エチルカルボジイミド（EDCまたはWSC）、Ｎ,Ｎ-カルボニルジイミダゾール（CDI）などが挙げられる。
　上記反応は、必要に応じて塩基の存在下に行うことができる。塩基としては、前記製法１と同様のものなどが挙げられ、これらの１種又は２種以上を適宜選択、混合して使用することができる。
　上記反応の反応温度は、通常０℃～２００℃、反応時間は、通常１分～４８時間で行うことができる。 The above reaction can be carried out in the presence of a solvent. As a solvent, the same thing as the said manufacturing method 1 etc. are mentioned, These 1 type (s) or 2 or more types can be selected suitably.
The above reaction can be carried out in the presence of a condensing agent as necessary. Examples of the condensing agent include dicyclohexylcarbodiimide (DCC), N- (3-dimethylaminopropyl) -N′-ethylcarbodiimide (EDC or WSC), N, N-carbonyldiimidazole (CDI), and the like.
The above reaction can be carried out in the presence of a base as necessary. Examples of the base include those similar to those in Production Method 1, and one or more of these can be appropriately selected and mixed for use.
The reaction temperature for the above reaction is usually from 0 ° C to 200 ° C, and the reaction time is usually from 1 minute to 48 hours.
　製法〔２－３〕 Manufacturing method [2-3]
　上記反応は、溶媒の存在下に行うことができる。溶媒としては、前記製法１と同様のものなどが挙げられ、これらの１種又は２種以上を適宜選択、混合して使用することができる。
　上記反応は、ハロゲン化剤の存在下に行うことができる。ハロゲン化剤としては、塩化オキサリル、塩化チオニルなどが挙げられる。
　上記反応の反応温度は、通常０℃～２００℃、反応時間は、通常１分～４８時間で行うことができる。 The above reaction can be carried out in the presence of a solvent. Examples of the solvent include those similar to those in Production Method 1, and one or more of these can be appropriately selected and mixed for use.
The above reaction can be carried out in the presence of a halogenating agent. Examples of the halogenating agent include oxalyl chloride and thionyl chloride.
The reaction temperature for the above reaction is usually from 0 ° C to 200 ° C, and the reaction time is usually from 1 minute to 48 hours.
　本発明に係る化合物は、除草剤の有効成分として使用した場合に、優れた除草効果を示す。その適用範囲は、水田、畑地、果樹園、桑園などの農耕地、山林、農道、グランド、工場敷地などの非農耕地と多岐にわたり、適用方法も土壌処理、茎葉処理、湛水処理等を適宜選択できる。 The compound according to the present invention exhibits an excellent herbicidal effect when used as an active ingredient of a herbicide. The range of application ranges widely from agricultural fields such as paddy fields, upland fields, orchards, mulberry fields, and non-agricultural land such as forests, farm roads, grounds, and factory sites. Applicable methods include soil treatment, foliage treatment, and flooding treatment as appropriate. You can choose.
　本発明に係る化合物は、一年生雑草や多年生雑草などの広範囲の望ましくない植物を防除することができる。具体的には、例えばイヌビエ又はタイヌビエ(barnyardgrass (Echinochloa crus-galli L.、Echinochloa oryzicola vasing.))、メヒシバ(crabgrass (Digitaria sanguinalis L.、Digitaria ischaemum Muhl. 、Digitaria adscendens Henr. 、Digitaria microbachne Henr. 、Digitaria horizontalis Willd.))、エノコログサ(green foxtail (Setaria viridis L.))、アキノエノコログサ(giant foxtail (Setaria faberiHerrm.))、キンエノコロ (yellow foxtail (Setaria lutescens Hubb.))、オヒシバ(goosegrass (Eleusine indica L.))、カラスムギ(wild oat (Avena fatua L.))、セイバンモロコシ(johnsongrass (Sorghum halepense L.))、シバムギ(quackgrass (Agropyron repens L.))、ビロードキビ(alexandergrass (Brachiaria plantaginea))、ギネアキビ（guineagrass (Panicum maximum Jacq.)）、パラグラス(paragrass (Panicum purpurascens))、オオクサキビ（smooth witchgrass (Panicum dichotomiflorum)、アゼガヤ(sprangletop (Leptochloa chinensis))、イトアゼガヤ(red sprangletop (Leptochloa panicea))、スズメノカタビラ(annual bluegrass (Poa annua L.))、スズメノテッポウ(black grass (Alopecurus myosuroides Huds.))、カモジグサ(cholorado bluestem (Agropyron tsukushiense (Honda) Ohwi))、メリケンニクキビ(broadleaf signalgrass(Brachiaria platyphylla Nash))、シンクリノイガ(southern sandbur (Cenchrus echinatus L.))、ネズミムギ(italian ryegrass (Lolium multiflorum Lam.))、ギョウギシバ(bermudagrass (Cynodon dactylon Pers.))のようなイネ科雑草(gramineae)；コゴメガヤツリ(rice flatsedge (Cyperus iria L.))、ハマスゲ(purple nutsedge (Cyperus rotundus L.))、キハマスゲ(yellow nutsedge (Cyperus esculentus L.))、ホタルイ(Japanese bulrush (Scirpus juncoides))、ミズガヤツリ(flatsedge (Cyperus serotinus))、タマガヤツリ(small-flower umbrellaplant (Cyperus difformis))、マツバイ(slender spikerush (Eleocharis acicularis))、クログワイ(water chestnut (Eleocharis kuroguwai))のようなカヤツリグサ科雑草(cyperaceae)；ウリカワ(Japanese ribbon waparo (Sagittaria pygmaea))、オモダカ(arrow-head (Sagittaria trifolia))、ヘラオモダカ(narrowleaf waterplantain (Alisma canaliculatum))のようなオモダカ科雑草(alismataceae)；コナギ(monochoria (Monochoria vaginalis))、ミズアオイ(monochoria species (Monochoria korsakowii))のようなミズアオイ科雑草(pontederiaceae)；アゼナ(false pimpernel (Lindernia pyxidaria))のようなアゼトウガラシ科雑草(linderniaceae)；アブノメ(abunome (Dopatrium junceum))のようなオオバコ科雑草(plantaginaceae)；キカシグサ(toothcup (Rotala india))、ヒメミソハギ(red stem (Ammannia multiflora))のようなミソハギ科雑草(lythraceae)；ミゾハコベ(long stem waterwort(Elatine triandra SCHK.))のようなミゾハコベ科雑草(elatinaceae)；イチビ(velvetleaf (Abutilon theophrastiMEDIC.))、アメリカキンゴジカ(prickly sida (Sida spinosaL.))のようなアオイ科雑草(malvaceae)；オナモミ(common cocklebur (Xanthium strumarium L.))、ブタクサ(common ragweed (Ambrosia elatior L.))、エゾノキツネアザミ(thistle (Breea setosa (BIEB.) KITAM.))、ハキダメギク(hairy galinsoga(Galinsoga ciliata Blake)) 、カミツレ(wild chamomile(Matricaria chamomilla L.))、ホトケノザ(henbit (Lamium amplexicaule L.))、セイヨウタンポポ（common dandelion (Taraxacum officinale weber)）、ヒメムカシヨモギ（horseweed (Erigeron Canadensis L.)）のようなキク科雑草(compositae)；イヌホウズキ(black nightshade (Solanum nigrum L.))、シロバナチョウセンアサガオ(jimsonweed (Datura stramonium))のようなナス科雑草(solanaceae)；アオビユ(slender amaranth (Amaranthus viridis L.))、アオゲイトウ(redroot pigweed (Amaranthus retroflexus L.)) シロザ(common lambsquarters (Chenopodium album L.)) 、ホウキギ(mexican burningbush(Kochia scoparia Schrad.))のようなヒユ科雑草(amaranthaceae)；サナエタデ(pale smartweed (Polygonum lapathifolium L.))、ハルタデ（ladysthumb (Polygonum persicaria L.)）、ソバカズラ(wild buckwheat(Polygonum convolvulus L.)) 、ミチヤナギ(knotweed(Polygonum aviculare L.))のようなタデ科雑草（polygonaceeae）；タネツケバナ(flexuous bittercress (Cardamine flexuosa WITH.))、ナズナ（shepherd’s-purse(Capsella bursapastoris Medik.)）、セイヨウカラシナ(indian mustard(Brassica juncea Czern.))のようなアブラナ科雑草（cruciferae）；マルバアサガオ(tall morningglory (Ipomoea purpurea L.))、セイヨウヒルガオ(field bindweed (Convolvulus arvensis L.))、アメリカアサガオ（ivyleaf morningglory (Ipomoea hederacea Jacq.)）のようなヒルガオ科雑草(convolvulaceae)；スベリヒユ(common purslane (Portulaca oleracea L.))のようなスベリヒユ科雑草（Portulacaceae）；エビスグサ(sicklepod (Cassia obtusifolia L.))のようなマメ科雑草（fabaceae）；ハコベ(common chickweed (Stellariamedia L.))のようなナデシコ科雑草（caryophyllaceae）；ヤエムグラ(catchweed (Galium spurium L.))のようなアカネ科雑草（rubiaceae）；エノキグサ(threeseeded copperleaf (Acalypha australis L.))のようなトウダイグサ科雑草（euphorbiaceae）；ツユクサ（common dayflower (Commelina communis L.)）のようなツユクサ科雑草（Commelinaceae）などの各種有害雑草を防除することができる。よって、有用作物、例えばトウモロコシ(corn (Zea mays L.))、ダイズ(soybean (Glycine max Merr.))、ワタ (cotton (Gossypiumspp.))、コムギ(wheat (Triticum spp.))、イネ(rice (Oryza sativa L.))、オオムギ(barley (Hordeum Vulgare L.))、ライムギ(rye (Secalecereale L.))、エンバク(oat (Avena sativaL.))、ソルガム(sorgo (Sorghum bicolor Moench))、アブラナ(rape (Brassica napus L.))、ヒマワリ(sunflower (Helianthus annuus L.))、テンサイ(sugar beet (Beta Vulgaris L.))、サトウキビ(suger cane (Saccharum officinarum L.))、芝(japanese lawngrass (Zoysia japonica stend))、ピーナッツ(peanut (Arachis hypogaea L.))、アマ(flax (Linum usitatissimum L.))、タバコ(tobacco (Nicotiana tabacum L.))、コーヒー(coffee (Coffea spp.))などの栽培において、選択的に有害雑草を防除する場合或いは非選択的に有害雑草を防除する場合において有効に使用される。 The compounds according to the present invention can control a wide range of undesirable plants such as annual and perennial weeds. Specifically, for example, barnyardgrass or barnyardgrass (barnyardgrass (Echinochloa crus-galli L. , Echinochloa oryzicola vasing.)), Crabgrass (crabgrass (Digitaria sanguinalis L., Digitaria ischaemum Muhl., Digitaria adscendens Henr., Digitaria microbachne Henr., Digitaria horizontalis Willd.)), Green foxtail ( Setaria viridis L.)), Akino foxtail ( Setaria faberi Herrm.)), Yellow foxtail ( Setaria lutescens Hubb.), Goosegrass ( Eleusine indica ) .)), Oats (wild oat ( Avena fatua L.)), sorghum sorghum (johnsongrass ( Sorghum halepense L.)), shibamugi (quackgrass ( Agropyron repens L.)), velvet millet (alexandergrass ( Brachiaria plantaginea )), guinea millet guineagrass ( Panicum maximum Jacq.)), paragrass ( Panicum purpurascens ), yellow squirrel (smooth witchgrass ( Panicum dichotomiflorum ), azegaya (sprangletop ( Lep tochloa chinensis)), Itoazegaya (red sprangletop (Leptochloa panicea)) , annual bluegrass (annual bluegrass (Poa annua L.) ), foxtail (black grass (Alopecurus myosuroides Huds. )), Kamojigusa (cholorado bluestem (Agropyron tsukushiense (Honda ) Ohwi )), Meriken Nik millet (broadleaf signalgrass (Brachiaria platyphylla Nash) ), Shinkurinoiga (southern sandbur (Cenchrus echinatus L.) ), darnel (italian ryegrass (Lolium multiflorum Lam. )), bermudagrass (bermudagrass (Cynodon dactylon Pers.) ) weed grasses (gramineae) such as; Cyperus Iria (rice flatsedge (Cyperus iria L.) ), purple nutsedge (purple nutsedge (Cyperus rotundus L.) ), yellow nutsedge (yellow nutsedge (Cyperus esculentus L.) ), bulrush (Japanese bulrush ( Scirpus juncoides )), Japanese squirrel (flatsedge ( Cyperus serotinus )), Japanese cypress (small-flower umbrellaplant ( Cyperus difformis )), Japanese pine (slender spikerush ( Eleocharis) acicularis)), water chestnut (water chestnut (Eleocharis kuroguwai)) Cyperaceae weeds (cyperaceae) such as; arrowhead (Japanese ribbon waparo (Sagittaria pygmaea) ), Alismataceae (arrow-head (Sagittaria trifolia) ), alisma canaliculatum (narrowleaf waterplantain ( Alisma canaliculatum)) Alismataceae weeds (alismataceae) such as; vaginalis (monochoria (monochoria vaginalis)), monochoria korsakowii (pontederiaceae weeds such as monochoria species (monochoria korsakowii)) ( pontederiaceae); false pimpernel (false pimpernel (Lindernia pyxidaria) Linderniaceae such as); plantain weed such as abunome ( Dopatrium junceum ); plantaginaceae; such as toothcup ( Rotala india ); red stem ( Ammannia multiflora ) Lythraceae weeds (elatinaceae) such as long stem waterwort ( Elatine triandra SCHK.); Malvaceae such as vetleaf ( Abutilon theophrasti MEDIC.)), American buckthorn (prickly sida ( Sida spinosa L.)); common fowl (common cocklebur ( Xanthium strumarium L.)), common ragweed ( Ambrosia) elatior L.)), Ezo fox thistle (thistle ( Breea setosa (BIEB.) KITAM.)), Hagyamegiku (hairy galinsoga ( Galinsoga ciliata Blake)), chamomile (wild chamomile ( Matricaria chamomilla L.)), Lamium amplexicaule L.)), dandelion ( Taraxacum officinale weber), horseweed ( Erigeron Canadensis L.)), compositae; black nightshade ( Solanum nigrum L.)), Solanaceae such as jimsonweed ( Datura stramonium ); slender amaranth ( Amaranthus viridis L.), redroot pigweed ( Amaranthus retroflexus L.) mmon lambsquarters (Chenopodium album L.)) , kochia (mexican burningbush (Kochia scoparia Schrad. )) Amaranthaceae weeds such as (amaranthaceae); Sanaetade (pale smartweed (Polygonum lapathifolium L.) ), Harutade (ladysthumb (Polygonum persicaria L .)), Buckwheat (wild buckwheat ( Polygonum convolvulus L.)), weeping ( Polygonum aviculare L.)), weeds (polygonaceeae); radish (flexuous bittercress ( Cardamine flexuosa WITH.)), crabiferae (cruciferae) such as shepherd's-purse ( Capsella bursapastoris Medik.) and Indian mustard ( Brassica juncea Czern.); tall morningglory ( Ipomoea purpurea L.), convolvulus bindweed ( Convolvulus arvensis L.)), convolvulaceae like common morning glory (ivyleaf morningglory ( Ipomoea hederacea Jacq.)); common purslane ( Portulaca ole Portulacaceae such as racea L.); legume weeds such as picklepod ( Cassia obtusifolia L.); weevil such as common chickweed ( Stellariamedia L.)) Weeds (caryophyllaceae); Rubiaceae weeds such as catchweed ( Galium spurium L.); Rubiaceae weeds such as threeseeded copperleaf ( Acalypha australis L.); common dayflower Various harmful weeds such as Commelinaceae such as ( Commelina communis L.) can be controlled. Therefore, useful crops such as corn (corn ( Zea mays L.)), soybean (soybean ( Glycine max Merr.)), Cotton (cotton ( Gossypium spp.)), Wheat (wheat ( Triticum spp.)), Rice ( rice ( Oryza sativa L.)), barley (barley ( Hordeum Vulgare L.)), rye (rye ( Secalecereale L.)), oat (oat ( Avena sativa L.)), sorghum (sorgo ( Sorghum bicolor Moench)) Rape , Brassica napus L., sunflower ( Helianthus annuus L.), sugar beet ( Beta Vulgaris L.), sugar cane (suger cane ( Saccharum officinarum L.)), turf lawngrass ( Zoysia japonica stend )), peanuts (peanut ( Arachis hypogae a L.)), flax (flax ( Linum usitatissimum L.)), tobacco (tobacco ( Nicotiana tabacum L.)), coffee (coffee ( Coffea spp.) ) Etc., it is used effectively when controlling harmful weeds selectively or when controlling non-selective harmful weeds.
　本発明に係る化合物は、通常各種農業上の補助剤と混合して粉剤、粒剤、顆粒水和剤、水和剤、錠剤、丸剤、カプセル剤（水溶性フィルムで包装する形態を含む）、水性懸濁剤、油性懸濁剤、マイクロエマルジョン製剤、サスポエマルジョン製剤、水溶剤、乳剤、液剤、ペースト剤などの形態に製剤調製し、施用することができるが、本発明の目的に適合するかぎり、通常の当該分野で用いられているあらゆる製剤形態にすることができる。 The compound according to the present invention is usually mixed with various agricultural adjuvants, powders, granules, granule wettable powders, wettable powders, tablets, pills, capsules (including forms packaged with water-soluble films). , Aqueous suspension, oil suspension, microemulsion formulation, suspoemulsion formulation, aqueous solvent, emulsion, solution, paste, etc. can be prepared and applied, but fits the purpose of the present invention As long as it is, it can be in any formulation form commonly used in the art.
　製剤に使用する補助剤としては、珪藻土、消石灰、炭酸カルシウム、タルク、ホワイトカーボン、カオリン、ベントナイト、カオリナイト及びセリサイトの混合物、クレー、炭酸ナトリウム、重曹、芒硝、ゼオライト、澱粉などの固形担体；水、トルエン、キシレン、ソルベントナフサ、ジオキサン、アセトン、イソホロン、メチルイソブチルケトン、クロロベンゼン、シクロヘキサン、ジメチルスルホキシド、ジメチルホルムアミド、ジメチルアセトアミド、Ｎ－メチル－２－ピロリドン、アルコールなどの溶剤；脂肪酸塩、安息香酸塩、アルキルスルホコハク酸塩、ジアルキルスルホコハク酸塩、ポリカルボン酸塩、アルキル硫酸エステル塩、アルキル硫酸塩、アルキルアリール硫酸塩、アルキルジグリコールエーテル硫酸塩、アルコール硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アリールスルホン酸塩、リグニンスルホン酸塩、アルキルジフェニルエーテルジスルホン酸塩、ポリスチレンスルホン酸塩、アルキルリン酸エステル塩、アルキルアリールリン酸塩、スチリルアリールリン酸塩、ポリオキシエチレンアルキルエーテル硫酸エステル塩、ポリオキシエチレンアルキルアリールエーテル硫酸塩、ポリオキシエチレンアルキルアリールエーテル硫酸エステル塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルアリールリン酸エステル塩、ポリオキシエチレンアリールエーテルリン酸エステル塩、ナフタレンスルホン酸塩ホルマリン縮合物、アルキルナフタレンスルホン酸塩ホルマリン縮合物のような陰イオン系の界面活性剤や展着剤；ソルビタン脂肪酸エステル、グリセリン脂肪酸エステル、脂肪酸ポリグリセライド、脂肪酸アルコールポリグリコールエーテル、アセチレングリコール、アセチレンアルコール、オキシアルキレンブロックポリマー、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンスチリルアリールエーテル、ポリオキシエチレングリコールアルキルエーテル、ポリエチレングリコール、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ポリオキシエチレングリセリン脂肪酸エステル、ポリオキシエチレン硬化ヒマシ油、ポリオキシプロピレン脂肪酸エステルのような非イオン系の界面活性剤や展着剤；オリーブ油、カポック油、ひまし油、シュロ油、椿油、ヤシ油、ごま油、トウモロコシ油、米ぬか油、落花生油、綿実油、大豆油、菜種油、亜麻仁油、きり油、液状パラフィンなどの植物油や鉱物油などが挙げられる。これら補助剤は本発明の目的から逸脱しないかぎり、1種又は2種以上を適宜選択して使用することができ、また、例えば、増量剤、増粘剤、沈降防止剤、凍結防止剤、分散安定剤、薬害軽減剤、防黴剤、発泡剤、崩壊剤、結合剤など、通常使用される各種補助剤も使用することができる。本発明に係る化合物と各種補助剤との配合割合は、0.1：99.9～95：5、望ましくは0.2：99.8～85：15である。 Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite and sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; Water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, alcohol and other solvents; fatty acid salts, benzoic acid Salt, alkylsulfosuccinate, dialkylsulfosuccinate, polycarboxylate, alkylsulfate, alkylsulfate, alkylarylsulfate, alkyldiglycolethersulfate, alcohol Sulfate ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester, alkyl aryl phosphate, styryl Aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate Salt, polyoxyethylene aryl ether phosphate ester salt, naphthalene sulfonate formalin condensate, alkyl naphthalene sulfonate formalin condensate Surfactants and spreading agents; sorbitan fatty acid ester, glycerin fatty acid ester, fatty acid polyglyceride, fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl Aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene Nonionic surfactants and spreading agents such as fatty acid esters; olive oil, kapok oil, Examples include vegetable oils and mineral oils such as castor oil, palm oil, straw oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, persimmon oil, and liquid paraffin. These adjuvants can be used by appropriately selecting one or two or more kinds without departing from the object of the present invention. For example, extenders, thickeners, anti-settling agents, antifreeze agents, dispersion agents Various commonly used adjuvants such as stabilizers, safeners, antifungal agents, foaming agents, disintegrating agents, binders and the like can also be used. The compounding ratio of the compound according to the present invention and various adjuvants is 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.
　本発明に係る化合物を含有する除草剤の施用量（除草有効量）は、気象条件、土壌条件、製剤形態、対象となる望ましくない植物の種類、施用時期などの相違により一概に規定できないが、一般に１ヘクタール当り本発明に係る化合物が0.1～5,000ｇ、望ましくは0.5～3,000ｇとなるように施用する。本発明には、このような除草剤の施用による望ましくない植物の防除方法も含まれる。 The application rate (herbicidally effective amount) of the herbicide containing the compound according to the present invention cannot be defined unconditionally due to differences in weather conditions, soil conditions, formulation forms, types of undesirable plants targeted, application time, etc. In general, it is applied so that the compound according to the present invention is 0.1 to 5,000 g, preferably 0.5 to 3,000 g per hectare. The present invention also includes a method for controlling undesirable plants by applying such herbicides.
　また、本発明に係る化合物を含有する除草剤は、他の農薬、肥料、薬害軽減剤などと混用或いは併用することができ、この場合に一層優れた効果、作用性を示すことがある。他の農薬としては、除草剤、殺菌剤、抗生物質、植物ホルモン、殺虫剤などが挙げられる。特に、本発明に係る化合物と、他の除草剤の有効成分である化合物の１種又は２種以上とを混用或いは併用した混合除草性組成物は、適用草種の範囲、薬剤処理の時期、除草活性等を好ましい方向へ改良することが可能である。尚、本発明に係る化合物と他の除草剤の有効成分である化合物は、各々別々に製剤したものを散布時に混合して使用しても、両者を一緒に製剤して使用してもよい。本発明には、上記した混合除草性組成物も含まれる。 In addition, the herbicide containing the compound according to the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners and the like, and in this case, more excellent effects and activities may be exhibited. Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like. In particular, the mixed herbicidal composition in which the compound according to the present invention and one or more compounds as active ingredients of other herbicides are used in combination or in combination, the range of the applicable herbaceous species, the timing of drug treatment, It is possible to improve the herbicidal activity and the like in a preferable direction. In addition, the compound which is the active ingredient of the compound which concerns on this invention and another herbicide may mix and use it at the time of dispersion | distribution, respectively, or may use both together. The above-described mixed herbicidal composition is also included in the present invention.
　本発明に係る化合物と他の除草剤の有効成分である化合物との混合比は、気象条件、土壌条件、薬剤の製剤形態、施用時期、施用方法などの相違により一概に規定できないが、本発明に係る化合物１重量部に対し、他の除草剤は有効成分である化合物を１種あたり0.001～10,000重量部、望ましくは0.01～1,000重量部配合する。また、施用適量は１ヘクタール当りの有効成分の総化合物量として0.1～10,000ｇ、望ましくは0.2～5,000ｇである。本発明には、このような混合除草組成物の施用による望ましくない植物の防除方法も含まれる。 The mixing ratio between the compound according to the present invention and the compound that is an active ingredient of other herbicides cannot be defined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application time, application method, etc. Other herbicides are compounded in an amount of 0.001 to 10,000 parts by weight, preferably 0.01 to 1,000 parts by weight, as an active ingredient for other herbicides. The appropriate amount to be applied is 0.1 to 10,000 g, preferably 0.2 to 5,000 g as the total amount of active ingredients per hectare. The present invention also includes a method for controlling undesirable plants by application of such a mixed herbicidal composition.
　他の除草剤の有効成分である化合物としては、下記化合物（一般名；一部ＩＳＯ申請中を含む）を例示することができるが、特に記載がない場合であっても、これら化合物に塩、アルキルエステル等が存在する場合は、当然それらも含まれる。 Examples of the compound that is an active ingredient of other herbicides include the following compounds (generic names; some of which are included in the application for ISO). If an alkyl ester or the like is present, it is naturally included.
　（１）２，４－Ｄ、２，４－Ｄブトチル（2,4-D-butotyl）、２，４－Ｄブチル（2,4-D-butyl）、２，４－Ｄジメチルアンモニウム（2,4-D-dimethylammonium）、２，４－Ｄジオールアミン（2,4-D-diolamine）、２，４－Ｄエチル（2,4-D-ethyl）、２，４－Ｄ－２－エチルヘキシル（2,4-D-2-ethylhexyl）、２，４－Ｄイソブチル（2,4-D-isobutyl）、２，４－Ｄイソオクチル（2,4-D-isoctyl）、２，４－Ｄイソプロピル（2,4-D-isopropyl）、２，４－Ｄイソプロピルアンモニウム（2,4-D-isopropylammonium）、２，４－Ｄナトリウム（2,4-D-sodium）、２，４－Ｄイソプロパノールアンモニウム（2,4-D-isopropanolammonium）、２，４－Ｄトロールアミン（2,4-D-trolamine）、２，４－ＤＢ、２，４－ＤＢブチル（2,4-DB-butyl）、２，４－ＤＢジメチルアンモニウム（2,4-DB-dimethylammonium）、２，４－ＤＢイソオクチル（2,4-DB-isoctyl）、２，４－ＤＢカリウム（2,4-DB-potassium）、２，４－ＤＢナトリウム（2,4-DB-sodium）、２，４－Ｄコリン塩（2,4-D choline salt）、ジクロロプロップ（dichlorprop）、ジクロロプロップブトチル（dichlorprop-butotyl）、ジクロロプロップジメチルアンモニウム（dichlorprop-dimethylammonium）、ジクロロプロップイソオクチル（dichlorprop-isoctyl）、ジクロロプロップカリウム（dichlorprop-potassium）、ジクロロプロップ－Ｐ（dichlorprop-P）、ジクロロプロップ－Ｐジメチルアンモニウム（dichlorprop-P-dimethylammonium）、ジクロロプロップ－Ｐカリウム（dichlorprop-P-potassium）、ジクロロプロップ－Ｐナトリウム（dichlorprop-P-sodium）、ＭＣＰＡ、ＭＣＰＡブトチル（MCPA-butotyl）、ＭＣＰＡジメチルアンモニウム（MCPA-dimethylammonium）、ＭＣＰＡ－２－エチルヘキシル（MCPA-2-ethylhexyl）、ＭＣＰＡカリウム（MCPA-potassium）、ＭＣＰＡナトリウム（MCPA-sodium）、ＭＣＰＡチオエチル（MCPA-thioethyl）、ＭＣＰＢ、ＭＣＰＢエチル（MCPB-ethyl）、ＭＣＰＢナトリウム（MCPB-sodium）、メコプロップ（mecoprop）、メコプロップブトチル（mecoprop-butotyl）、メコプロップナトリウム（mecoprop-sodium）、メコプロップ－Ｐ（mecoprop-P）、メコプロップ－Ｐブトチル（mecoprop-P-butotyl）、メコプロップ－Ｐジメチルアンモニウム（mecoprop-P-dimethylammonium）、メコプロップ－Ｐ－２－エチルヘキシル（mecoprop-P-2-ethylhexyl）、メコプロップ－Ｐカリウム（mecoprop-P-potassium）、ナプロアニリド（naproanilide）、クロメプロップ（clomeprop）、HIA-1のようなフェノキシ系化合物；２，３，６－ＴＢＡ、ジカンバ（dicamba）、ジカンバブトチル（dicamba-butotyl）、ジカンバジグリコールアミン（dicamba-diglycolamine）、ジカンバジメチルアンモニウム（dicamba-dimethylammonium）、ジカンバジオールアミン（dicamba-diolamine）、ジカンバイソプロピルアンモニウム（dicamba-isopropylammonium）、ジカンバカリウム（dicamba-potassium）、ジカンバナトリウム（dicamba-sodium）、ピクロラム（picloram）、ピクロラムジメチルアンモニウム（picloram-dimethylammonium）、ピクロラムイソオクチル（picloram-isoctyl）、ピクロラムカリウム（picloram-potassium）、ピクロラムトリイソプロパノールアンモニウム（picloram-triisopropanolammonium）、ピクロラムトリイソプロピルアンモニウム（picloram-triisopropylammonium）、ピクロラムトロールアミン（picloram-trolamine）、トリクロピル（triclopyr）、トリクロピルブトチル（triclopyr-butotyl）、トリクロピルトリエチルアンモニウム（triclopyr-triethylammonium）、クロピラリド（clopyralid）、クロピラリドオールアミン（clopyralid-olamine）、クロピラリドカリウム（clopyralid-potassium）、クロピラリドトリイソプロパノールアンモニウム（clopyralid-triisopropanolammonium）、アミノピラリド（aminopyralid）、アミノシクロピラクロール（aminocyclopyrachlor）、ハロウキシフェン（halauxifen）、ハロウキシフェンメチル（halauxifen-methyl）のような芳香族カルボン酸系化合物；その他、ナプタラム（naptalam）、ナプタラムナトリウム（naptalam-sodium）、ベナゾリン（benazolin）、ベナゾリンエチル（benazolin-ethyl）、キンクロラック（quinclorac）、キンメラック（quinmerac）、ダイフルフェンゾピル（diflufenzopyr）、ダイフルフェンゾピルナトリウム（diflufenzopyr-sodium）、フルオキシピル（fluroxypyr）、フルオキシピル－２－ブトキシ－１－メチルエチル（fluroxypyr-2-butoxy-1-methylethyl）、フルオキシピルメプチル（fluroxypyr-meptyl）、クロロフルレノール（chlorflurenol）、クロロフルレノールメチル（chlorflurenol-methyl）、クラシフォス（clacyfos）などのように植物のホルモン作用を攪乱することで除草効力を示すとされている化合物。 (1) 2,4-D, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-dimethylammonium (2 , 4-D-dimethylammonium), 2,4-D-diolamine, 2,4-D-ethyl, 2,4-D-2-ethylhexyl (2,4-D-2-ethylhexyl), 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl (2,4-D-isopropyl), 2,4-D-isopropylammonium, 2,4-D sodium (2,4-D-sodium), 2,4-D isopropanolammonium (2,4-D-isopropanolammonium), 2,4-D-trolamine, 2,4-DB, 2,4-DB-butyl, 2 , 4-DB-dimethylammonium, 2,4-DB-iso Cutyl (2,4-DB-isoctyl), 2,4-DB potassium (2,4-DB-potassium), 2,4-DB sodium (2,4-DB-sodium), 2,4-D choline salt (2,4-D choline salt), dichloroprop (dichlorprop), dichloroprop-butotyl, dichloroprop-dimethylammonium, dichloroprop-isoctyl, dichloroprop potassium ( dichlorprop-potassium), dichloroprop-P (dichlorprop-P), dichloroprop-P-dimethylammonium, dichloroprop-P-potassium, dichloroprop-P-potassium, dichlorprop-P P-sodium), MCPA, MCPA-butotyl, MCPA-dimethylammonium, MCPA-2-ethyl MCPA-2-ethylhexyl, MCPA potassium (MCPA-potassium), MCPA sodium (MCPA-sodium), MCPA-thioethyl (MCPA-thioethyl), MCPB, MCPB-ethyl (MCPB-ethyl), MCPB-sodium (MCPB-sodium) , Mecoprop, mecoprop-butotyl, mecoprop-sodium, mecoprop-P, mecoprop-P-butotyl, mecoprop-P-dimethyl Ammonium (mecoprop-P-dimethylammonium), mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, naproanilide, clomeprop, HIA- Phenoxy compounds such as 1, 2,3,6-TBA, dicamba, dicamba-butoty l), dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium ), Dicamba-sodium, picloram, picloram-dimethylammonium, picloram-isoctyl, picloram-potassium, picloram Lamb triisopropanolammonium (picloram-triisopropylammonium), picloram-trolamine, triclopyr, triclopyr-butotyl, triclopyr Triech Ammonium (triclopyr-triethylammonium), clopyralid (clopyralid), clopyralid-olamine, clopyralid-potassium, clopyralid-triisopropanolammonium, aminopyralide (aminopyralid), aminocyclopyrchlor (amino) ), Aromatic carboxylic acid compounds such as halauxifen and halauxifen-methyl; naptalam, naptalam-sodium, benazolin, benazoline ethyl (Benazolin-ethyl), quinclorac, quinmerac, diflufenzopyr, diflufenzopyr-sodium, fluroxypyr, Ruoxypyr-2-butoxy-1-methylethyl, fluroxypyr-meptyl, chloroflurenol, chloroflurenol-methyl, A compound that has been shown to have herbicidal activity, such as clacyfos, by disrupting the hormonal action of plants.
　（２）クロロトルロン(chlorotoluron)、ジウロン（diuron）、フルオメツロン(fluometuron)、リニュロン（linuron）、イソプロチュロン（isoproturon）、メトベンズロン（metobenzuron）、テブチウロン(tebuthiuron)、ジメフロン（dimefuron）、イソウロン（isouron）、カルブチレート（karbutilate）、メタベンズチアズロン（methabenzthiazuron）、メトクスロン（metoxuron）、メトブロムロン (metoburomuron)、モノリニュロン（monolinuron）、ネブロン（neburon）、シデュロン（siduron）、ターブメトン（terbumeton）、トリエタジン（trietazine）のような尿素系化合物；シマジン（simazine）、アトラジン（atrazine）、アトラトン（atratone）、シメトリン（simetryn）、プロメトリン（prometryn）、ジメタメトリン（dimethametryn）、ヘキサジノン(hexazinone)、メトリブジン（metribuzin）、ターブチラジン（terbuthylazine）、シアナジン（cyanazine）、アメトリン（ametryn）、シブトリン（cybutryne）、ターブトリン(terbutryn)、プロパジン（propazine）、メタミトロン（metamitron）、プロメトン（prometon）のようなトリアジン系化合物；ブロマシル（bromacil）、ブロマシルリチウム（bromacyl-lithium）、レナシル（lenacil）、ターバシル(terbacil)のようなウラシル系化合物；プロパニル（propanil）、シプロミッド（cypromid）のようなアニリド系化合物；スエップ（swep）、デスメディファム(desmedipham)、フェンメディファム（phenmedipham）のようなカーバメート系化合物；ブロモキシニル（bromoxynil）、ブロモキシニルオクタノエート（bromoxynil-octanoate）、ブロモキシニルヘプタノエート（bromoxynil-heptanoate）、アイオキシニル（ioxynil）、アイオキシニルオクタノエート（ioxynil-octanoate）、アイオキシニルカリウム（ioxynil-potassium）、アイオキシニルナトリウム（ioxynil-sodium）のようなヒドロキシベンゾニトリル系化合物；その他、ピリデート（pyridate）、ベンタゾン（bentazone）、ベンタゾンナトリウム（bentazone-sodium）、アミカルバゾン（amicarbazone）、メタゾール（methazole）、ペンタノクロール（pentanochlor）などのように植物の光合成を阻害することで除草効力を示すとされている化合物。 (2) chlorotoluron, diuron, fluometuron, linuron, isoproturon, metobenzuron, tebuthiuron, dimefuron, isouron, isouron Carbutilate, methabenzthiazuron, metoxuron, metoburomuron, monolinuron, neburon, siduron, terbumeton, triazine Ureazine compounds: simazine, atrazine, atratone, simetryn, prometryn, dimethametryn, hexazinone, metribuzin, tubutila Triazine compounds such as terbuthylazine, cyanazine, ametryn, cybutryne, terbutryn, propazine, metamitron, and prometon; bromacil Uracil compounds such as bromacyl-lithium, lenacil, terbacil; anilide compounds such as propanil, cypromid; swep, desmedifam (desmedipham), carbamate compounds such as phenmedipham; bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, ioxynil Ioxynyl octanoate (ioxy Hydroxybenzonitrile compounds such as nil-octanoate, ioxynil-potassium, and ioxynil-sodium; others, pyridate, bentazone, bentazone sodium Sodium, amicarbazone, methazole, pentanochlor, and other compounds that are said to exhibit herbicidal activity by inhibiting plant photosynthesis.
　（３）それ自身が植物体中でフリーラジカルとなり、活性酸素を生成させて速効的な除草効力を示すとされているパラコート（paraquat）、ジクワット（diquat）のような４級アンモニウム塩系化合物。 (3) Quaternary ammonium salt compounds such as paraquat and diquat, which are said to themselves become free radicals in the plant body and generate active oxygen to show rapid herbicidal efficacy.
　（４）ニトロフェン（nitrofen）、クロメトキシフェン（chlomethoxyfen）、ビフェノックス（bifenox）、アシフルオルフェン（acifluorfen）、アシフルオルフェンナトリウム（acifluorfen-sodium）、ホメサフェン（fomesafen）、ホメサフェンナトリウム（fomesafen-sodium）、オキシフルオルフェン（oxyfluorfen）、ラクトフェン（lactofen）、アクロニフェン（aclonifen）、エトキシフェンエチル（ethoxyfen-ethyl）、フルオログリコフェンエチル（fluoroglycofen-ethyl）、フルオログリコフェン（fluoroglycofen）のようなジフェニルエーテル系化合物；クロルフタリム（chlorphthalim）、フルミオキサジン（flumioxazin）、フルミクロラック（flumiclorac）、フルミクロラックペンチル（flumiclorac-pentyl）、シニドンエチル（cinidon-ethyl）、フルチアセットメチル（fluthiacet-methyl）、EK-5385のような環状イミド系化合物；その他、オキサジアルギル（oxadiargyl）、オキサジアゾン（oxadiazon）、スルフェントラゾン（sulfentrazone）、カルフェントラゾンエチル（carfentrazone-ethyl）、チジアジミン（thidiazimin）、ペントキサゾン（pentoxazone）、アザフェニジン（azafenidin）、イソプロパゾール（isopropazole）、ピラフルフェンエチル（pyraflufen-ethyl）、ベンズフェンジゾン（benzfendizone）、ブタフェナシル（butafenacil）、サフルフェナシル（saflufenacil）、フルアゾレート（fluazolate）、プロフルアゾール（profluazol）、フルフェンピルエチル（flufenpyr-ethyl）、ベンカルバゾン（bencarbazone）、チアフェナシル (tiafenacil)、ピラクロニル(pyrachlonil)、HNPC-B4047、IR-6396、EK-5439、EK-5498、SYN-523、WO2008/008763に記載の化合物などのように植物のクロロフィル生合成を阻害し、光増感過酸化物質を植物体中に異常蓄積させることで除草効力を示すとされている化合物。 (4) Nitrofen, Chlomethoxyfen, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, fomesafen-sodium ), Oxyfluorfen, lactofen, aclonifen, ethoxyfen-ethyl, fluoroglycofen-ethyl, fluoroglycofen, and other diphenyl ether compounds; Chlorphthalim, flumioxazin, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet-methyl, EK-5385 Other cyclic imide compounds; oxadiargyl, oxadiazon, sulfentrazone, carfentrazone-ethyl, thidiazimin, pentoxazone, azafenidin ), Isopropazole, pyraflufen-ethyl, benzfendizone, butafenacil, saflufenacil, fluazolate, profluazol, profluazol, full Fenpyrethyl (flufenpyr-ethyl), bencarbazone, tiafenacil, pyaflonon, HNPC-B4047, IR-6396, EK-5439, EK-5498, SYN-523, WO2008 / 008763 Inhibits plant chlorophyll biosynthesis like compounds , Compounds photosensitizer peroxide material is to exhibit herbicidal activity by causing abnormal accumulation in the plant.
　（５）ノルフルラゾン（norflurazon）、クロリダゾン（chloridazon）、メトフルラゾン（metflurazon）のようなピリダジノン系化合物；ピラゾリネート（pyrazolynate）、ピラゾキシフェン（pyrazoxyfen）、ベンゾフェナップ（benzofenap）、トプラメゾン(topramezone)、ピラスルフォトール（pyrasulfotole）のようなピラゾール系化合物；その他、アミトロール(amitrole)、フルリドン（fluridone）、フルルタモン（flurtamone）、ジフルフェニカン（diflufenican）、メトキシフェノン（methoxyphenone）、クロマゾン（clomazone）、スルコトリオン（sulcotrione）、メソトリオン（mesotrione）、テンボトリオン（tembotrione）、テフリルトリオン（tefuryltrione）、フェンキノトリオン(fenquinotrione)、シクロピリモレート（cyclopyrimorate）、イソキサフルトール（isoxaflutole）、ジフェンゾコート（difenzoquat）、ジフェンゾコートメチルサルフェート（difenzoquat-metilsulfate）、イソキサクロロトール（isoxachlortole）、ベンゾビシクロン（benzobicyclon）、ビシクロピロン（bicyclopyron）、ピコリナフェン（picolinafen）、ビフルブタミド（beflubutamid）、ケトスピラドックス（ketospiradox）、ケトスピラドックスカリウム（ketospiradox-potassium）、JP2012-2571記載化合物などのようにカロチノイドなどの植物の色素生合成を阻害し、白化作用を特徴とする除草効力を示すとされている化合物。 (5) Pyridazinone compounds such as norflurazon, chloridazon, metflurazon; pyrazolynate, pyrazoxifene, benzofenap, topramezone, and pyrazole photole. Pyrazole compounds such as (pyrasulfotole); others, amitrole, fluridone, flurtamone, diflufenican, methoxyphenone, clomazone, sulcotrione, mesotrione (Mesotrione), tembotrione, tefuryltrione, fenquinotrione, cyclopyrimorate, isoxaflutole, difenzo coat ( difenzoquat, difenzoquat-metilsulfate, isoxachlortole, benzobicyclon, bicyclopyron, picolinafen, biflubutamide, ketospiradox ( Ketospiradox), ketospiradox-potassium, compounds described in JP2012-2571, etc., which inhibit the pigment biosynthesis of plants such as carotenoids and are said to show herbicidal activity characterized by whitening action.
　（６）ジクロホップメチル（diclofop-methyl）、ジクロホップ（diclofop）、ピリフェノップナトリウム（pyriphenop-sodium）、フルアジホップブチル（fluazifop-butyl）、フルアジホップ（fluazifop）、フルアジホップ-Ｐ（fluazifop-P）、フルアジホップ－Ｐ－ブチル（fluazifop-P-butyl）、ハロキシホップメチル（haloxyfop-methyl）、ハロキシホップ（haloxyfop）、ハロキシホップエトチル（haloxyfop-etotyl）、ハロキシホップ－Ｐ（haloxyfop-P）、ハロキシホップ－Ｐ－メチル（haloxyfop-P-methyl）、キザロホップエチル（quizalofop-ethyl）、キザロホップ－Ｐ（quizalofop-P）、キザロホップ－Ｐ－エチル（quizalofop-P-ethyl）、キザロホップ－Ｐ－テフリル（quizalofop-P-tefuryl）、シハロホップブチル（cyhalofop-butyl）、フェノキサプロップエチル（fenoxaprop-ethyl）、フェノキサプロップ－Ｐ（fenoxaprop-P）、フェノキサプロップ－Ｐ－エチル（fenoxaprop-P-ethyl）、メタミホッププロピル（metamifop-propyl）、メタミホップ（metamifop）、クロジナホッププロパルギル（clodinafop-propargyl）、クロジナホップ（clodinafop）、プロパキザホップ（propaquizafop）、HNPC-A8169、SYP-1924のようなアリールオキシフェノキシプロピオン酸系化合物；アロキシジムナトリウム（alloxydim-sodium）、アロキシジム（alloxydim）、クレソジム（clethodim）、セトキシジム（sethoxydim）、トラルコキシジム（tralkoxydim）、ブトロキシジム（butroxydim）、テプラロキシジム（tepraloxydim）、プロホキシジム（profoxydim）、シクロキシジム（cycloxydim）のようなシクロヘキサンジオン系化合物；ピノキサデン（pinoxaden）のようなフェニルピラゾリン系化合物;などのように脂肪酸の生合成を阻害し、植物に除草効力を示すとされている化合物。 (6) Dicloofop-methyl, diclofop, pyriphenop-sodium, fluazifop-butyl, fluazifop, fluazifop-P (fluazifop-P) , Fluazifop-P-butyl, Haloxyfop-methyl, Haloxyfop, Haloxyfop-etotyl, Haloxyfop-P, Haloxyhop -P-methyl, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-ethyl (quizalofop-P-ethyl) quizalofop-P-tefuryl), cyhalofop-butyl, fenoxaprop-ethyl, phenoxaprop- (Fenoxaprop-P), fenoxaprop-P-ethyl, metamifop-propyl, metamifop, clodinafop-propargyl, clodinafop Aryloxyphenoxypropionic compounds such as propaquizafop, HNPC-A8169, and SYP-1924; alloxydim-sodium, alloxydim, clethodim, sethoxydim, Cyclohexanedione compounds such as tralkoxydim, butroxydim, tepraloxydim, prooxydim, cycloxydim; phenylpyrazoline compounds such as pinoxaden; etc. Inhibits biosynthesis of fatty acids And, the compounds to exhibit herbicidal activity plants.
　（７）クロリムロンエチル（chlorimuron-ethyl）、クロリムロン（chlorimuron）、スルホメツロンメチル（sulfometuron-methyl）、スルホメツロン（sulfometuron）、プリミスルフロンメチル（primisulfuron-methyl）、プリミスルフロン（primisulfuron）、ベンスルフロンメチル（bensulfuron-methyl）、ベンスルフロン（bensulfuron）、クロルスルフロン（chlorsulfuron）、メトスルフロンメチル（metsulfuron-methyl）、メトスルフロン（metsulfuron）、シノスルフロン（cinosulfuron）、ピラゾスルフロンエチル（pyrazosulfuron-ethyl）、ピラゾスルフロン（pyrazosulfuron）、フラザスルフロン（flazasulfuron）、リムスルフロン（rimsulfuron）、ニコスルフロン（nicosulfuron）、イマゾスルフロン（imazosulfuron）、フルセトスルフロン（flucetosulfuron）、シクロスルファムロン（cyclosulfamuron）、プロスルフロン（prosulfuron）、フルピルスルフロンメチルナトリウム（flupyrsulfuron-methyl-sodium）、フルピルスルフロン（flupyrsulfuron）、トリフルスルフロンメチル（triflusulfuron-methyl）、トリフルスルフロン（triflusulfuron）、ハロスルフロンメチル（halosulfuron-methyl）、ハロスルフロン（halosulfuron）、チフェンスルフロンメチル（thifensulfuron-methyl）、チフェンスルフロン（thifensulfuron）、エトキシスルフロン（ethoxysulfuron）、オキサスルフロン（oxasulfuron）、エタメトスルフロン（ethametsulfuron）、エタメトスルフロンメチル（ethametsulfuron-methyl）、イオドスルフロン（iodosulfuron）、イオドスルフロンメチルナトリウム（iodosulfuron-methyl-sodium）、スルフォスルフロン（sulfosulfuron）、トリアスルフロン（triasulfuron）、トリベヌロンメチル（tribenuron-methyl）、トリベヌロン（tribenuron）、トリトスルフロン（tritosulfuron）、フォーラムスルフロン（foramsulfuron）、トリフルオキシスルフロン（trifloxysulfuron）、トリフルオキシスルフロンナトリウム（trifloxysulfuron-sodium）、メソスルフロンメチル（mesosulfuron-methyl）、メソスルフロン（mesosulfuron）、オルソスルファムロン（orthosulfamuron）、アミドスルフロン（amidosulfuron）、アジムスルフロン (azimsulfuron)、プロピリスルフロン（propyrisulfuron）、メタゾスルフロン (metazosulfuron)、メチオピルスルフロン (methiopyrsulfuron)、モノスルフロンメチル(monosulfuron-methyl)、オルソスルフロン(orsosulfuron) 、イオフェンスルフロン（iofensulfuron）、イオフェンスルフロンナトリウム（iofensulfuron-sodium）のようなスルフォニルウレア化合物；フルメツラム（flumetsulam）、メトスラム（metosulam）、ジクロスラム（diclosulam）、クロランスラムメチル（cloransulam-methyl）、フロラスラム（florasulam）、ペノクススラム(penoxsulam)、ピロクススラム（pyroxsulam）のようなトリアゾロピリミジンスルホンアミド系化合物；イマザピル（imazapyr）、イマザピルイソプロピルアンモニウム（imazapyr-isopropylammonium）、イマゼタピル（imazethapyr）、イマゼタピルアンモニウム（imazethapyr-ammonium）、イマザキン（imazaquin）、イマザキンアンモニウム（imazaquin-ammonium）、イマザモックス（imazamox）、イマザモックスアンモニウム（imazamox-ammonium）、イマザメタベンズ（imazamethabenz）、イマザメタベンズメチル（imazamethabenz-methyl）、イマザピック（imazapic）のようなイミダゾリノン系化合物；ピリチオバックナトリウム（pyrithiobac-sodium）、ビスピリバックナトリウム（bispyribac-sodium）、ピリミノバックメチル（pyriminobac-methyl）、ピリベンゾキシム（pyribenzoxim）、ピリフタリド（pyriftalid）、ピリミスルファン（pyrimisulfan）、トリアファモン（triafamone）のようなピリミジニルサリチル酸系化合物；フルカーバゾン（flucarbazone）、フルカーバゾンナトリウム（flucarbazone-sodium）、プロポキシカーバゾンナトリウム（propoxycarbazone-sodium）、プロポキシカーバゾン（propoxycarbazone）、チエンカルバゾンメチル(thiencarbazone-methyl)のようなスルホニルアミノカルボニルトリアゾリノン系化合物；その他、グリホサート（glyphosate）、グリホサートナトリウム（glyphosate-sodium）、グリホサートカリウム（glyphosate-potassium）、グリホサートアンモニウム（glyphosate-ammonium）、グリホサートジアンモニウム（glyphosate-diammonium）、グリホサートイソプロピルアンモニウム（glyphosate-isopropylammonium）、グリホサートトリメシウム（glyphosate-trimesium）、グリホサートセスキナトリウム（glyphosate-sesquisodium）、グルホシネート（glufosinate）、グルホシネートアンモニウム（glufosinate-ammonium）、グルホシネート-Ｐ（glufosinate-Ｐ）、グルホシネート-Ｐアンモニウム（glufosinate-Ｐ-ammonium）、グルホシネート-Ｐナトリウム（glufosinate-Ｐ-sodium）、ビラナホス（bilanafos）、ビラナホスナトリウム（bilanafos-sodium）、シンメチリン（cinmethylin）などのように植物のアミノ酸生合成を阻害することで除草効力を示すとされている化合物。 (7) Chlorimuron-ethyl, chlorimuron, sulfometuron-methyl, sulfometuron, primisulfuron-methyl, primisulfuron, Bensulfuron-methyl, bensulfuron, chlorsulfuron, methsulfuron-methyl, metsulfuron, cinosulfuron, pyrazosulfuron-ethyl , Pyrazosulfuron, flazasulfuron, rimsulfuron, nicosulfuron, imazosulfuron, flucetosulfuron, cyclosulfamuron, prosulfur Prosulfuron, flupirsulfuron-methyl-sodium, flupirsulfuron, triflusulfuron-methyl, triflusulfuron, halosulfuron-methyl , Halosulfuron, thifensulfuron-methyl, thifensulfuron, ethoxysulfuron, oxasulfuron, ethametsulfuron, ethamethsulfuron methyl ( ethametsulfuron-methyl, iodosulfuron, sodium iodosulfuron-methyl-sodium, sulfosulfuron, triasulfuron, tribenuron-methyl, tribenuron (Tribenuron), tritosulfuron, trisulfoxyon (foramsulfuron), trifloxysulfuron, trifloxysulfuron-sodium, mesosulfuron-methyl, mesosulfuron , Orthosulfamuron, amidosulfuron, azimsulfuron, propyrisulfuron, metazosulfuron, methiopyrsulfuron, monosulfuron methyl (monosulfuron methyl) Sulphonylurea compounds, such as, orthosulfuron, iofensulfuron, iofensulfuron-sodium; flumetsulam, metosulam, di Triazolopyrimidine sulfonamide compounds such as diclosulam, cloransulam-methyl, florasulam, penoxsulam, pyroxsulam; imazapyr, imazapyr isopropylammonium (Imazapyr-isopropylammonium), imazetapyr (imazethapyr), imazethapyr-ammonium, imazaquin, imazaquin-ammonium, imazamox, imazamox-ammonium , Imazamethabenz, imazamethabenz-methyl, imidazolinone compounds such as imazapic; pyrithiobac-sodium, bispyribac-so pyrimidinyl salicylic acid compounds such as dium), pyriminobac-methyl, pyribenzoxim, pyrifalid, pyrimisulfan, triafamone; flucarbazone, full carbazone Sulfonylaminocarbonyltriazolinone compounds such as sodium (flucarbazone-sodium), propoxycarbazone sodium (propoxycarbazone-sodium), propoxycarbazone, thiencarbazone-methyl; others, glyphosate ), Sodium glyphosate-sodium, potassium glyphosate-potassium, glyphosate-ammonium, glyphosate-diammonium, glyphosate isopate Pyrammonium (glyphosate-isopropylammonium), glyphosate-trimesium, glyphosate-sesquisodium, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P Amino acid biosynthesis of plants, such as P ammonium (glufosinate-P-ammonium), glufosinate-P sodium (glufosinate-P-sodium), vilanafos (bilanafos), vilanafos sodium (bilanafos-sodium), cinmethylin A compound that is said to show herbicidal efficacy by inhibiting.
　（８）トリフルラリン（trifluralin）、オリザリン（oryzalin）、ニトラリン（nitralin）、ペンディメタリン（pendimethalin）、エタルフルラリン（ethalfluralin）、ベンフルラリン（benfluralin）、プロジアミン（prodiamine）、ブトラリン（butralin）、ジニトラミン（dinitramine）のようなジニトロアニリン系化合物；ベンスリド（bensulide）、ナプロパミド（napropamide）、ナプロパミド-M（napropamide-M）、プロピザミド（propyzamide、プロナミド（pronamide））のようなアミド系化合物；アミプロホスメチル（amiprofos-methyl）、ブタミホス（butamifos）、アニロホス（anilofos）、ピペロホス（piperophos）のような有機リン系化合物；プロファム（propham）、クロルプロファム（chlorpropham）、バーバン（barban）、カルベタミド（carbetamide）のようなフェニルカーバメート系化合物；ダイムロン（daimuron）、クミルロン（cumyluron）、ブロモブチド（bromobutide）、メチルダイムロン（methyldymron）のようなクミルアミン系化合物；その他、アシュラム（asulam）、アシュラムナトリウム（asulam-sodium）、ジチオピル（dithiopyr）、チアゾピル（thiazopyr）、クロルタールジメチル（chlorthal-dimethyl）、クロルタール（chlorthal）、ジフェナミド（diphenamid）、フラムプロップ－Ｍ－メチル（flamprop-M-methyl）、フラムプロップ－Ｍ（flamprop-M）、フラムプロップ－Ｍ－イソプロピル（flamprop-M-isopropyl）などのように植物の細胞有糸分裂を阻害することで除草効力を示すとされている化合物。 (8) Trifluralin, oryzalin, oryzalin, nitalin, pendimethalin, ethalluralin, benfluralin, prodiamine, butralin, dinitramine ( dinitroamine compounds such as dinitramine; amide compounds such as bensulide, napropamide, napropamide-M, propyzamide, pronamide; amiprophosmethyl (pronamide) Organophosphorus compounds such as amiprofos-methyl, butamifos, anilofos, piperophos; such as propham, chlorpropham, barban, carbetamide Naive phenyl carbamate compounds ; Cumylamine compounds such as daimuron, cumyluron, bromobutide, methyldymron; other, ashram, asuram-sodium, dithiopyr, thiazopyr ( thiazopyr), chlorthal dimethyl, chlorthal, diphenamid, flamprop-M-methyl, flamprop-M, flamprop-M -Compounds such as isopropyl (flamprop-M-isopropyl) that are said to show herbicidal efficacy by inhibiting plant cell mitosis.
　（９）アラクロール（alachlor）、メタザクロール（metazachlor）、ブタクロール（butachlor）、プレチラクロール（pretilachlor）、メトラクロール（metolachlor）、Ｓ－メトラクロール（S-metolachlor）、テニルクロール（thenylchlor）、ペトキサマイド(pethoxamid)、アセトクロール（acetochlor）、プロパクロール（propachlor）、ジメテナミド（dimethenamide）、ジメテナミド－Ｐ（dimethenamide－Ｐ）、プロピソクロール（propisochlor）、ジメタクロール（dimethachlor）のようなクロロアセトアミド系化合物；モリネート（molinate）、ジメピペレート（dimepiperate）、ピリブチカルブ（pyributicarb）、ＥＰＴＣ、ブチレート（butylate）、ベルノレート（vernolate）、ペブレート（pebulate）、シクロエート（cycloate）、プロスルホカルブ（prosulfocarb）、エスプロカルブ（esprocarb）、チオベンカルブ（thiobencarb）、ジアレート（diallate）、トリアレート（tri-allate）、オルベンカルブ（orbencarb）のようなチオカーバメート系化合物；その他、エトベンザニド（etobenzanid）、メフェナセット（mefenacet）、フルフェナセット（flufenacet）、トリディファン（tridiphane）、カフェンストロール（cafenstrole）、フェントラザミド（fentrazamide）、オキサジクロメフォン（oxaziclomefone）、インダノファン（indanofan）、ベンフレセート（benfuresate）、ピロキサスルフォン（pyroxasulfone）、フェノキサスルフォン（fenoxasulfone）、メチオゾリン（methiozolin）、ダラポン（dalapon）、ダラポンナトリウム（dalapon-sodium）、ＴＣＡナトリウム（TCA-sodium）、トリクロロ酢酸（trichloroacetic acid）などのように植物のタンパク質生合成あるいは脂質生合成を阻害することで除草効力を示すとされている化合物。 (9) Alachlor, metazachlor, butachlor, pretilachlor, metolachlor, S-metolachlor, tenylchlor, petoxaxide Chloroacetamide compounds such as acetochlor, acetochlor, propachlor, dimethenamide, dimethenamide-P, propisochlor, dimethachlor; molinate Dimepiperate, pyributicarb, EPTC, butyrate, vernolate, pebulate, cycloate, prosulfocarb, esprocarb, chi Thiocarbamate compounds such as thiobencarb, dialate, diallate, tri-allate, orbencarb; etobenzanid, mefenacet, flufenacet, tri Didiphane, caffenstrole, fentrazamide, oxaziclomefone, indanofan, benfuresate, pyroxasulfone, fenoxasulfone, methiozoline To inhibit plant protein biosynthesis or lipid biosynthesis, such as methiozolin, dalapon, dalapon-sodium, TCA sodium (TCA-sodium), trichloroacetic acid. The compound which is supposed to show herbicidal efficacy in.
　（１０）ジクロベニル（dichlobenil）、トリアジフラム（triaziflam）、インダジフラム（indaziflam）、フルポキサム（flupoxam）、イソキサベン（isoxaben）などのように植物のセルロース生合成を阻害することで除草効力を示すとされている化合物。 (10) Compounds that exhibit herbicidal activity by inhibiting cellulose biosynthesis in plants such as dichlobenil, triaziflam, indaziflam, flupoxam, isoxaben, etc. .
　（１１）ＭＳＭＡ、ＤＳＭＡ、ＣＭＡ、エンドタール（endothall）、エンドタールジカリウム（endothall-dipotassium）、エンドタールナトリウム（endothall-sodium）、エンドタールモノ(Ｎ，Ｎ－ジメチルアルキルアンモニウム)（endothall-mono(N,N-dimethylalkylammonium)）、エトフメセート（ethofumesate）、ソディウムクロレート（sodium chlorate）、ペラルゴン酸（pelargonic acid、ノナン酸（nonanoic acid））、ホスアミン（fosamine）、ホスアミンアンモニウム（fosamine-ammonium）、イプフェンカルバゾン（ipfencarbazone）、アクロレイン（aclolein）、スルファミン酸アンモニウム（ammonium sulfamate）、ボラックス（borax）、クロロ酢酸（chloroacetic acid）、クロロ酢酸ナトリウム（sodium chloroacete）、シアナミド（cyanamide）、メチルアルソン酸（methylarsonic acid）、ジメチルアルソン酸（dimethylarsinic acid）、ジメチルアルソン酸ナトリウム（sodium dimethylarsinate）、ジノターブ（dinoterb）、ジノターブアンモニウム（dinoterb-ammonium）、ジノターブジオールアミン（dinoterb-diolamine）、ジノターブアセテート（dinoterb-acetate）、ＤＮＯＣ、硫酸第一鉄（ferrous sulfate）、フルプロパネート（flupropanate）、フルプロパネートナトリウム（flupropanate-sodium）、メフルイジド（mefluidide）、メフルイジドジオールアミン（mefluidide-diolamine）、メタム（metam）、メタムアンモニウム（metam-ammonium）、メタムカリウム（metam-potassium）、メタムナトリウム（metam-sodium）、イソチオシアン酸メチル（methyl isothiocyanate）、ペンタクロロフェノール（pentachlorophenol）、ペンタクロロフェノールナトリウム（sodium pentachlorophenoxide）、ペンタクロロフェノールラウレート（pentachlorophenol laurate）、キノクラミン（quinoclamine）、硫酸（sulfuric acid）、ウレアサルフェート（urea sulfate）、ザンチノシン（xanthinosin）、ハービマイシン（herbimycin）、アングイノール（unguinol）、メタチロシン（metatyrosine）、サルメンチン（sarmentine）、タキシトミンA（thaxtominA）、メバロシジン（mevalocidin）、α-リモネン（alpha-limonene）、ピリバムベンズプロピル（pyribambenz-propyl）、ピリバムベンズイソプロピル（pyribambenz-isopropyl）、JS-913、KHG-23844、H-9201、SIOC-0163、SIOC-0171、SIOC-0172、SIOC-0285、SIOC-0426、SIOC-H-057、ZJ-0166、ZJ-1835、ZJ-0453、ZJ-0777、ZJ-0862、WO2008/096398記載の化合物などのその他の除草剤。 (11) MSMA, DSMA, CMA, endothal (endothall), endothal-dipotassium, endothal sodium (endothall-sodium), endtal mono (N, N-dimethylalkylammonium) (endothall-mono ( N, N-dimethylalkylammonium)), etofumesate, sodium chlorate, pelargonic acid, nonanoic acid, fosamine, fosamine-ammonium, ipfen Carbazone (ipfencarbazone), aclolein, ammonium sulfamate, borax, chloroacetic acid, sodium chloroacete, cyanamide, methylarsonic acid ), Dimethylarso Dimethylarsinic acid, sodium dimethylarsinate, dinoterb, dinoterb-ammonium, dinoterb-diolamine, dinoterb-acetate, DNOC , Ferrous sulfate (flurus プ ロ sulfate), flupropanate, flupropanate-sodium, mefluidide, mefluidide-diolamine, metam, metam Ammonium (metam-ammonium), metam-potassium, metam-sodium, methyl isothiocyanate, pentachlorophenol, pentachlorophenol sodium, pentachlorophenol La Rate (pentachlorophenol 、 laurate), quinoclamine, sulfuric acid, ureasulfate, xanthinosin, herbimycin, anguinol, metatyrosine, salmentine, Taxitomin A, mevalocidin, alpha-limonene, pyribambenz-propyl, pyribambenz-isopropyl, JS-913, KHG-23844, H- 9201, SIOC-0163, SIOC-0171, SIOC-0172, SIOC-0285, SIOC-0426, SIOC-H-057, ZJ-0166, ZJ-1835, ZJ-0453, ZJ-0777, ZJ-0862, WO2008 / Other herbicides such as the compounds described in 096398.
　（１２）ザントモナス　キャンペストリス（Xanthomonas campestris）、エピココロシルス　ネマトソルス（Epicoccosirus nematosorus）、エピココロシルス　ネマトスペラス（Epicoccosirus nematosperus）、エキセロヒラム　モノセラス（Exserohilum monoseras）、ドレクスレラ　モノセラス（Drechsrela monoceras）などのように植物に寄生することで除草効力を示すとされているもの。 (12) Xanthomonas campestris (Xanthomonas campestris), epi heart Sils Nematosorusu (Epicoccosirus nematosorus), epi heart Sils Nematosuperasu (Epicoccosirus nematosperus), Ekiserohiramu monoceras (Exserohilum monoseras), parasitic plants such as Drechslera monoceras (Drechsrela monoceras) It is supposed to show herbicidal efficacy by doing.
　本発明に係る化合物の望ましい態様として、以下のものが挙げられる。
（１）前記一般式（Ｉ）中、Ｒ１がＸで置換されてもよいフェニル、Ｃ１‐６アルキル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ２が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ１‐６ハロアルキル、Ｃ３‐６シクロアルキルＣ１‐６アルキル、Ｘで置換されてもよいフェニル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ４がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６アルキルＣ３‐８シクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６がＣ１‐６アルキル又はＸで置換されてもよいフェニルであり；Ｒ７がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル、Ｃ１‐６アルコキシカルボニル又はＣ３‐６シクロアルキルオキシカルボニルであり；ＡがＣＨ又は窒素原子であり；Ｒａ及びＲｂがそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘがハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルフィニル、Ｃ１‐６アルキルスルホニル、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６ハロアルキルチオ、ニトロ又はシアノであり；Ｙが酸素原子又は硫黄原子であり；Ｗ１が酸素原子であり；Ｗ２が酸素原子又は硫黄原子であり；ｎが０、１又は２である前記請求項１に記載の化合物又はその塩。 Preferred embodiments of the compound according to the present invention include the following.
(1) the formula (I), phenyl R 1 is optionally substituted with X, C 1 - 6 alkyl or C 1 - 6 alkoxy C 1 - 6 is alkyl; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, optionally substituted with X benzyl, cyano C 1-6 alkyl, - (CR a R b) n -C (O) R 5, - ( CR a R b) n -SO 2 -R 6 or - (CR a R b) be n -Y-R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 1 - 6 haloalkyl, C 3 - 6 cycloalkyl C 1 - 6 alkyl, phenyl or optionally substituted with X C 1 - 6 alkoxy C 1 - 6 is alkyl; R 4 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl, C 1 - 6 alkyl C 3 - 8 cycloalkyl, phenyl optionally substituted by X, which may be naphthyl substituted with X, which may be heterocyclic substituted with X, is substituted with X also good benzyl or -CH 2 -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, may be substituted with X phenoxy, heterocycle which may be substituted with X, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - 6 alkoxy C 1 - 6 is alkyl; R 6 is C 1 - 6 alkyl or there substituted with also phenyl with X; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, optionally substituted with X Phenyl, C 1 - 6 alkylcarbonyl, C 1 - 6 alkoxycarbonyl or C 3 - 6 cycloalkyl alkyloxycarbonyl; A is CH or a nitrogen atom; R a and R b are each independently hydrogen atom or C 1 - 6 is alkyl; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 alkylthio, C 1 - 6 alkyl sulfinyl, C 1 - 6 alkylsulfonyl, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 haloalkylthio, a nitro or cyano; Y is oxygen atom or sulfur atom; W 1 is an oxygen atom by and; W 2 is oxygen atom or sulfur atom; n is a compound according to claim 1 is 0, 1 or 2 or its Salt.
（２）前記一般式（Ｉ）中、Ｒ１がＸで置換されてもよいフェニル、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル又はＣ１‐６ハロアルキルであり；Ｒ２が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル又はＸで置換されてもよいフェニルであり；Ｒ４が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環又はジＣ１‐６アルキルアミノであり；Ｒ７はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル又はＣ１‐６アルコキシカルボニルであり；ＡがＣＨ又は窒素原子であり；Ｒａ及びＲｂがそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘがハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルホニル、ニトロ、シアノ又はフェニルであり；Ｙが酸素原子又は硫黄原子であり；Ｗ１が酸素原子又は硫黄原子であり；Ｗ２が酸素原子又は硫黄原子であり；ｎが０又は１である化合物又はその塩。 (2) In the general formula (I), R 1 is optionally substituted with X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl or C 1 - 6 haloalkyl; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted with X, which may be benzyl substituted by X, cyano C 1-6 alkyl, -(CR a R b ) n -C (O) R 5 ,-(CR a R b ) n -SO 2 -R 6 or-(CR a R b ) n -YR 7 ; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl Le, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl or there is substituted with also phenyl with X; R 4 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, phenyl optionally substituted by X, naphthyl which may be substituted by X, optionally substituted with X good heterocycle, 2 good benzyl or -CH be substituted with X -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, optionally substituted with X phenyl , which may be substituted by X phenoxy, heterocycle which may be substituted with X, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - 6 a Kokishi C 1 - 6 is alkyl; R 6 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, which may be substituted by X heterocycle or di C 1 - 6 alkylamino by and; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, C 1 - 6 alkylcarbonyl or C 1 - 6 alkoxycarbonyl carbonyloxy; A is CH or nitrogen atom There; independently R a and R b are each a hydrogen atom or a C 1 - 6 is alkyl; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 alkylthio, C 1 - 6 alkylsulfonyl, two B, cyano or phenyl; Y is oxygen atom or sulfur atom; W 1 is oxygen atom or sulfur atom; W 2 is oxygen atom or sulfur atom; n is 0 or 1 A compound or a salt.
　次に本発明の実施例を記載するが、本発明はこれらに限定されるものではない。まず、本発明に係る化合物の合成例を記載する。 Next, examples of the present invention will be described, but the present invention is not limited thereto. First, synthesis examples of the compounds according to the present invention will be described.
　合成例１
4‐(2‐クロロフェニル)‐2‐メチル‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（化合物No.1-23）の合成
　4‐(2‐クロロフェニル)‐2‐メチル‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボン酸（200 mg）とクロロホルム（2 ml）の混合溶液を攪拌し、そこに室温で塩化オキサリル（120 μl）及びDMF（1滴）を加えて、3時間攪拌した。クロロホルムと過剰の塩化オキサリルを減圧下留去した後、残渣をアセトニトリル（3 ml）に溶かした。そこに1‐メチル‐1H‐テトラゾール‐5‐アミン（140 mg）及びピリジン（170 μl）を加えて、マイクロウェーブを用いて130℃下、45分間攪拌した。反応液に水を加えた後、1N HCl水を加えてpH1～2に調整した。その溶液を酢酸エチルで抽出し、有機層を飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をヘプタン：酢酸エチル＝1：1で洗浄し、目的物（211 mg）を無色固体として得た。
1H-NMR (300 MHz, CDCl3) 11.03 (brs, 1H), 7.67-7.62 (m, 1H), 7.58-7.46 (m, 2H), 7.33-7.29 (m, 1H), 4.08 (s, 3H), 3.96 (s, 3H). Synthesis example 1
4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro-1,2,4- Synthesis of triazine-6-carboxamide (Compound No. 1-23) 4- (2-Chlorophenyl) -2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine A mixed solution of -6-carboxylic acid (200 mg) and chloroform (2 ml) was stirred, and oxalyl chloride (120 μl) and DMF (1 drop) were added thereto at room temperature, followed by stirring for 3 hours. Chloroform and excess oxalyl chloride were distilled off under reduced pressure, and the residue was dissolved in acetonitrile (3 ml). 1-Methyl-1H-tetrazol-5-amine (140 mg) and pyridine (170 μl) were added thereto, and the mixture was stirred at 130 ° C. for 45 minutes using a microwave. After adding water to the reaction solution, 1N HCl water was added to adjust the pH to 1-2. The solution was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with heptane: ethyl acetate = 1: 1 to obtain the desired product (211 mg) as a colorless solid.
1 H-NMR (300 MHz, CDCl 3 ) 11.03 (brs, 1H), 7.67-7.62 (m, 1H), 7.58-7.46 (m, 2H), 7.33-7.29 (m, 1H), 4.08 (s, 3H ), 3.96 (s, 3H).
　合成例２
エチル(4‐(2‐クロロフェニル)‐2‐メチル‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボニル)（1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)カルバメート（化合物No.3-18）の合成
　4‐(2‐クロロフェニル)‐2‐メチル‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（150 mg）とトルエン（4.1 ml）の混合懸濁液を攪拌し、そこに室温でエチルクロロホルメート（80 μl）及びピリジン（70 μl）を加えて、4時間攪拌した。反応液に水を加えて酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝1：2）で精製し、目的物（80 mg）を無色固体として得た。
1H-NMR(500 MHz, CDCl3) 7.60 (d, J=6.5 Hz, 1H), 7.50-7.44 (m, 2H), 7.28 (d, J=6.5 Hz, 1H), 4.31-4.20 (m, 2H), 3.97 (s, 3H), 3.80 (s, 3H), 1.21-1.19 (m, 3H). Synthesis example 2
Ethyl (4- (2-chlorophenyl) -2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonyl) (1-methyl-1H-tetrazole) -5-yl) carbamate (Compound No. 3-18) 4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo- A mixed suspension of 2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide (150 mg) and toluene (4.1 ml) was stirred and stirred at room temperature with ethyl chloroformate (80 μl) and pyridine (70 μl) were added and stirred for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (heptane: ethyl acetate = 1: 2) to obtain the desired product (80 mg) as a colorless solid.
1 H-NMR (500 MHz, CDCl 3 ) 7.60 (d, J = 6.5 Hz, 1H), 7.50-7.44 (m, 2H), 7.28 (d, J = 6.5 Hz, 1H), 4.31-4.20 (m, 2H), 3.97 (s, 3H), 3.80 (s, 3H), 1.21-1.19 (m, 3H).
　合成例３
1‐(4‐(2‐クロロフェニル)‐2‐メチル‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド)エチルエチルカルボネート（化合物No.3-39）の合成
　4‐(2‐クロロフェニル)‐2‐メチル‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（150 mg）とアセトニトリル（4 ml）の混合溶液を攪拌し、そこに室温で1‐クロロエチルエチルカルボネート（120 μl）及び炭酸カリウム（120 mg）を加えて、3時間加熱還流した。反応液に水を加えて酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝1：2）で精製し、目的物（70 mg）を油状物質として得た。 Synthesis example 3
1- (4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro-1,2 , 4-Triazine-6-carboxamido) ethyl ethyl carbonate (Compound No. 3-39) 4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-tetrazol-5-yl) A mixed solution of -3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carboxamide (150 mg) and acetonitrile (4 ml) was stirred at room temperature. -Chloroethyl ethyl carbonate (120 μl) and potassium carbonate (120 mg) were added, and the mixture was heated to reflux for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (heptane: ethyl acetate = 1: 2) to obtain the desired product (70 mg) as an oily substance.
　合成例４
4‐(2‐クロロフェニル)‐2‐メチル‐Ｎ‐(1‐メチル‐1Ｈ‐1,2,4‐トリアゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（化合物No.2-23）の合成
　4‐(2‐クロロフェニル)‐2‐メチル‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボン酸（287 mg）とクロロホルム（2 ml）の混合溶液を攪拌し、そこに室温で塩化オキサリル（170 μl）及びDMF（1滴）を加えて、2時間攪拌した。クロロホルムと過剰の塩化オキサリルを減圧下留去した後、残渣をアセトニトリル（3 ml）に溶かした。そこに1‐メチル‐1H‐トリアゾール‐5‐アミン（200 mg）及びピリジン（250 μl）を加えて、マイクロウェーブを用いて130℃下、1時間攪拌した。反応液に水を加えた後、1N HCl水を加えてpH1～2に調整した。その溶液を酢酸エチルで抽出し、有機層を飽和食塩水で洗浄、無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をヘプタン：酢酸エチル＝1：1で洗浄し、目的物（174 mg）を無色固体として得た。
1H-NMR(300 MHz, CDCl3) 7.81 (s, 1H), 7.66-7.61 (m, 1H), 7.54-7.48 (m, 2H), 7.33-7.28 (m, 1H), 3.94 (s, 3H), 3.86 (s, 3H). Synthesis example 4
4- (2-Chlorophenyl) -2-methyl-N- (1-methyl-1H-1,2,4-triazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro- Synthesis of 1,2,4-triazine-6-carboxamide (Compound No. 2-23) 4- (2-Chlorophenyl) -2-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1 , 2,4-Triazine-6-carboxylic acid (287 mg) and chloroform (2 ml) were stirred, and oxalyl chloride (170 μl) and DMF (1 drop) were added thereto at room temperature for 2 hours. Stir. Chloroform and excess oxalyl chloride were distilled off under reduced pressure, and the residue was dissolved in acetonitrile (3 ml). 1-Methyl-1H-triazol-5-amine (200 mg) and pyridine (250 μl) were added thereto, and the mixture was stirred at 130 ° C. for 1 hour using a microwave. After adding water to the reaction solution, 1N HCl water was added to adjust the pH to 1-2. The solution was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with heptane: ethyl acetate = 1: 1 to obtain the desired product (174 mg) as a colorless solid.
1 H-NMR (300 MHz, CDCl 3 ) 7.81 (s, 1H), 7.66-7.61 (m, 1H), 7.54-7.48 (m, 2H), 7.33-7.28 (m, 1H), 3.94 (s, 3H ), 3.86 (s, 3H).
　合成例５
2‐ターシャリーブチル‐4‐(2‐クロロフェニル)‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（化合物No.1-277）の合成
　2‐ターシャリーブチル‐4‐(2‐クロロフェニル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボン酸（150 mg）とクロロホルム（2.0 ml）の混合溶液を攪拌し、そこに室温で塩化オキサリル（80 μl）及びDMF（1滴）を加えて、2時間攪拌した。クロロホルムと過剰の塩化オキサリルを減圧下留去した後、残渣をアセトニトリル（3.0 ml）に溶かした。そこに1‐メチル‐1H‐テトラゾール‐5‐アミン（92 mg）及びピリジン（110 μl）を加えて、マイクロウェーブを用いて130℃下、45分間攪拌した。反応液を1N HCl水中に入れ、室温で30分攪拌した。その溶液を濾過して、乾燥し目的物（150 mg）を無色固体として得た。
1H-NMR(300 MHz, CDCl3) 11.01 (br s, 1H), 7.66-7.61 (m, 1H), 7.56-7.46 (m, 2H), 7.36-7.30 (m, 1H), 4.08 (s, 3H), 1.73 (s, 9H)). Synthesis example 5
2-tert-butyl-4- (2-chlorophenyl) -N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro-1,2, Synthesis of 4-triazine-6-carboxamide (Compound No. 1-277) 2-tertiarybutyl-4- (2-chlorophenyl) -3,5-dioxo-2,3,4,5-tetrahydro-1,2 , 4-Triazine-6-carboxylic acid (150 mg) and chloroform (2.0 ml) were mixed, and oxalyl chloride (80 μl) and DMF (1 drop) were added thereto at room temperature, followed by stirring for 2 hours. . Chloroform and excess oxalyl chloride were distilled off under reduced pressure, and the residue was dissolved in acetonitrile (3.0 ml). 1-Methyl-1H-tetrazol-5-amine (92 mg) and pyridine (110 μl) were added thereto, and the mixture was stirred at 130 ° C. for 45 minutes using a microwave. The reaction solution was put into 1N HCl water and stirred at room temperature for 30 minutes. The solution was filtered and dried to obtain the desired product (150 mg) as a colorless solid.
1 H-NMR (300 MHz, CDCl 3 ) 11.01 (br s, 1H), 7.66-7.61 (m, 1H), 7.56-7.46 (m, 2H), 7.36-7.30 (m, 1H), 4.08 (s, 3H), 1.73 (s, 9H)).
　合成例６
1‐(2‐ターシャリーブチル‐4‐(2‐クロロフェニル)‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド)エチルエチルカルボネート（化合物No.3-171）
　2‐ターシャリーブチル‐4‐(2‐クロロフェニル)‐Ｎ‐(1‐メチル‐1Ｈ‐テトラゾール‐5‐イル)‐3,5‐ジオキソ‐2,3,4,5‐テトラヒドロ‐1,2,4‐トリアジン‐6‐カルボキサミド（110 mg）とキシレン（5 ml）の混合懸濁液を攪拌し、そこに室温で1‐クロロエチルエチルカルボネート（124 mg）、炭酸カリウム（113 mg）及びヨウ化カリウム（14 mg）を加えて、3時間加熱還流した。反応液に水を加えて酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥後、溶媒を減圧下留去した。残渣をカラムクロマトグラフィー（ヘプタン：酢酸エチル＝2：3）で精製し、目的物（77 mg）を油状物質として得た。 Synthesis Example 6
1- (2-tert-butyl-4- (2-chlorophenyl) -N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro-1 , 2,4-Triazine-6-carboxamido) ethyl ethyl carbonate (Compound No.3-171)
2-tert-butyl-4- (2-chlorophenyl) -N- (1-methyl-1H-tetrazol-5-yl) -3,5-dioxo-2,3,4,5-tetrahydro-1,2, A mixed suspension of 4-triazine-6-carboxamide (110 mg) and xylene (5 ml) was stirred and stirred at room temperature with 1-chloroethyl ethyl carbonate (124 mg), potassium carbonate (113 mg) and iodine. Potassium chloride (14 mg) was added, and the mixture was heated to reflux for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (heptane: ethyl acetate = 2: 3) to obtain the desired product (77 mg) as an oily substance.
　次に、本発明に係る化合物の代表例を第１表から第３表に挙げる。これらの化合物は、前記合成例或いは前記した種々の製造方法に基づいて合成することができる。第１表から第３表中、物性欄に記載の数値は融点（℃）を示し、NMRと記載されている化合物はそれらの1H-NMRスペクトルデータを第４表に挙げる。尚、第１表から第４表中、No.は化合物番号を示す。また、表中、Meはメチル基を、Etはエチル基を、n-Prはノルマルプロピル基を、i-Prはイソプロピル基を、n-Buはノルマルブチル基を、s-Buはセカンダリーブチル基を、i-Buはイソブチル基を、t-Buはターシャリーブチル基を、n-Hexはノルマルヘキシル基を、Npはネオペンチル基を、c-Prはシクロプロピル基を、c-Buはシクロブチル基を、c-Penはシクロペンチル基を、c-Hexはシクロヘキシル基を、c-Hepはシクロへプチル基を、c-Octはシクロオクチル基を、Phはフェニル基を、Bnはベンジル基を各々示す。また、（3-CF3)Phは3位にCF3が置換したフェニル基を表し、(2,3-Cl2)Phは2位及び3位にClが置換したフェニル基を表し、(2-Cl-6-CF3)Phは2位にClが置換し、6位にCF3が置換したフェニル基を表し、(2-Cl)Bnはベンゼン環の2位にClが置換したベンジル基を表し、他の同様の記載もこれに準じる。 Next, typical examples of the compounds according to the present invention are listed in Tables 1 to 3. These compounds can be synthesized based on the above synthesis examples or the various production methods described above. In Tables 1 to 3, the numerical values described in the physical properties column indicate melting points (° C.), and for compounds described as NMR, their 1 H-NMR spectral data are listed in Table 4. In Tables 1 to 4, No. represents the compound number. In the table, Me is a methyl group, Et is an ethyl group, n-Pr is a normal propyl group, i-Pr is an isopropyl group, n-Bu is a normal butyl group, and s-Bu is a secondary butyl group. I-Bu is an isobutyl group, t-Bu is a tertiary butyl group, n-Hex is a normal hexyl group, Np is a neopentyl group, c-Pr is a cyclopropyl group, and c-Bu is a cyclobutyl group. C-Pen represents a cyclopentyl group, c-Hex represents a cyclohexyl group, c-Hep represents a cycloheptyl group, c-Oct represents a cyclooctyl group, Ph represents a phenyl group, and Bn represents a benzyl group. . (3-CF 3 ) Ph represents a phenyl group substituted with CF 3 at the 3-position, and (2,3-Cl 2 ) Ph represents a phenyl group substituted with Cl at the 2-position and the 3-position, (2 -Cl-6-CF 3 ) Ph represents a phenyl group substituted with Cl at the 2-position and CF 3 at the 6-position; (2-Cl) Bn represents a benzyl group substituted with Cl at the 2-position of the benzene ring And other similar descriptions are based on this.
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000006
Figure JPOXMLDOC01-appb-T000006
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000007
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000008
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000009
Figure JPOXMLDOC01-appb-T000010
Figure JPOXMLDOC01-appb-T000010
Figure JPOXMLDOC01-appb-T000011
Figure JPOXMLDOC01-appb-T000011
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000012
Figure JPOXMLDOC01-appb-T000013
Figure JPOXMLDOC01-appb-T000013
Figure JPOXMLDOC01-appb-T000014
Figure JPOXMLDOC01-appb-T000014
Figure JPOXMLDOC01-appb-T000015
Figure JPOXMLDOC01-appb-T000015
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000016
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000017
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000018
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000019
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000020
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000021
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000022
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000023
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000031
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000032
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000033
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000034
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000035
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000036
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000037
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000038
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000039
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000040
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000041
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000042
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000043
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000044
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000045
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000046
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000047
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000048
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000049
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000050
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000051
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000052
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000053
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000054
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000055
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000056
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000057
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000058
Figure JPOXMLDOC01-appb-T000059
Figure JPOXMLDOC01-appb-T000059
試験例１
　1／170,000ヘクタールポットに畑作土壌をつめ、各種植物の種子を播種した。その後、植物が一定の葉令（（１）イヌビエ(barnyardgrass (Echinochloa crus-galli L.))；0.5～3.0葉期、（２）メヒシバ(crabgrass (Digitaria sanguinalis L.))；0.5～3.0葉期、（３）エノコログサ(green foxtail (Setaria viridis L.))；1.5～3.5葉期、（４）アオゲイトウ(redroot pigweed (Amaranthus retroflexus L.))；0.2～2.5葉期、（５）アメリカキンゴジカ(prickly sida (Sida spinosa L.))；子葉～2.0葉期、（６）イチビ(velvetleaf (Abutilon theophrasti MEDIC.))；0.2～2.0葉期、（７）イネ(rice (Oryza sativa L.))；1.0～2.5葉期、（８）トウモロコシ(corn (Zea mays L.))；2.0～3.5葉期、（９）コムギ(wheat (Triticum spp.))；2.0～3.5葉期、（10）ワタ(cotton (Gossypium spp.))；初生葉～1.0葉期、（11）ダイズ(soybean (Glycine max Merr.))；初生葉～0.5葉期）に達したとき、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤を所定の有効成分量となるように秤量し、1ヘクタール当り500リットル相当の水（農業用展着剤（クサリノー：日本農薬株式会社製）を0.1容量％含有）に希釈した。調製した散布液を小型スプレーで茎葉処理した。 Test example 1
A field crop soil was filled 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) barbyard (crabgrass ( Digitaria sanguinalis L.)); 0.5-3.0 leaf stage (3) Green foxtail ( Setaria viridis L.); 1.5-3.5 leaf stage; (4) Red root pigweed ( Amaranthus retroflexus L.); 0.2-2.5 leaf stage; (5) American goldfish ( prickly sida ( Sida spinosa L.)); cotyledon to 2.0 leaves, (6) velvetleaf ( Abutilon theophrasti MEDIC.); 0.2 to 2.0 leaves, (7) rice (rice ( Oryza sativa L.)); 1.0 to 2.5 leaf stage, (8) corn (corn ( Zea mays L.)); 2.0 to 3.5 leaf stage, (9) wheat (wheat ( Triticum spp.)); 2.0 to 3.5 leaf stage, (10) cotton ( cotton ( Gossypium spp.)); primary leaf to 1.0 leaf stage, (11) soybean ( Glycine max Merr.); primary leaf to 0.5 leaf stage) Wettable powder prepared according to the method The emulsion was weighed to make a predetermined amount of active ingredient per hectare 500 liters water corresponding: diluted (agricultural spreader (Kusarino manufactured by Nihon Nohyaku) 0.1 volume% containing). The prepared spray was treated with a small spray.
　薬剤処理後、１４～２１日目に各種植物の生育状態を肉眼観察し、０（無処理区と同等）～１００（完全枯殺）の生育抑制率（％）で除草効果を評価し、第５表の結果を得た。 On the 14th to 21st days after the chemical treatment, the state of growth of various plants was observed with the naked eye, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed). The results in Table 5 were obtained.
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000060
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000062
Figure JPOXMLDOC01-appb-T000063
Figure JPOXMLDOC01-appb-T000063
　試験例２
　1／170,000ヘクタールポットに畑作土壌をつめ、各種植物（イヌビエ(barnyardgrass(Echinochloa crus-galli L.))、メヒシバ(crabgrass (Digitaria sanguinalis L.))、エノコログサ(green foxtail (Setaria viridis L.))、アオゲイトウ(redroot pigweed (Amaranthus retroflexus L.))、アメリカキンゴジカ(prickly sida (Sida spinosa L.))、イチビ(velvetleaf (Abutilon theophrasti MEDIC.))、イネ(rice (oryza sativa L.))、トウモロコシ(corn (Zea mays L.))、コムギ(wheat (Triticum spp.))、ワタ(cotton (Gossypium spp.))、ダイズ(soybean (Glycine max Merr.))）の種子を播種した。播種翌日、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤を所定の有効成分量となるように秤量し、１ヘクタール当り500リットル相当の水に希釈し、小型スプレーで土壌処理した。
　薬剤処理後、１４～２１日目に各種植物の生育状態を肉眼観察し、０（無処理区と同等）～１００（完全枯殺）の生育抑制率（％）で除草効果を評価し、第６表の結果を得た。 Test example 2
1 / 170,000 hectare pot filled with upland soil, various plants (barnyardgrass ( Echinochloa crus-galli L.)), barkyard (crabgrass ( Digitaria sanguinalis L.)), green foxtail (green foxtail ( Setaria viridis L.)), Red root pigweed ( Amaranthus retroflexus L.), American deer (prickly sida ( Sida spinosa L.)), green velvetleaf ( Abutilon theophrasti MEDIC.), Rice (rice ( oryza sativa L.)), maize ( Corn ( Zea mays L.)), wheat (wheat ( Triticum spp.)), cotton (cotton ( Gossypium spp.)), soybean (soybean ( Glycine max Merr.))) were sown. On the day after sowing, a wettable powder or emulsion prepared according to the usual formulation method of the compound according to the present invention is weighed so as to have a predetermined active ingredient amount, diluted in water equivalent to 500 liters per hectare, and a small spray Soil treatment.
On the 14th to 21st days after the chemical treatment, the state of growth of various plants was observed with the naked eye, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed). The results shown in Table 6 were obtained.
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000064
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000065
Figure JPOXMLDOC01-appb-T000066
Figure JPOXMLDOC01-appb-T000066
試験例３
　1／1,000,000ヘクタールポットに水田土壌を詰め、タイヌビエ(barnyardgrass (Echinochloa oryzicola vasing.))及びホタルイ(Japanese bulrush (Scirpus juncoides))の種子を播種し、その上に軽く覆土した。その後、湛水深0.5～1cmの状態で温室内に静置し、翌日にウリカワ(Japanese ribbon waparo (Sagittaria pygmaea))の塊茎を植え込んだ。その後、湛水深を3～4ｃｍに保ち、タイヌビエ及びホタルイが0.5葉期、ウリカワが初生葉期に達した時点で、本発明に係る化合物を通常の製剤方法に準じて調製した水和剤又は乳剤の水希釈液を、所定の有効成分量になるようにピペットで均一に滴下処理した。 Test example 3
Paddy soil was packed in a 1 / 1,000,000 hectare pot, and seeds of barnyardgrass ( Echinochloa oryzicola vasing.) And firefly (Japanese bulrush ( Scirpus juncoides )) were sown and lightly covered with soil. Thereafter, the tube was left in a greenhouse at a depth of 0.5 to 1 cm, and a tuber of Urikawa (Japanese ribbon waparo ( Sagittaria pygmaea )) was planted the next day. Thereafter, the water depth was maintained at 3 to 4 cm, and when the Tainubier and firefly reached the 0.5 leaf stage and Urikawa reached the primary leaf stage, the compound according to the present invention was prepared according to a conventional formulation method or a wettable powder or emulsion. The aqueous diluted solution was uniformly dropped with a pipette so as to obtain a predetermined active ingredient amount.
　薬剤処理後、１３～１５日目にタイヌビエ、ホタルイ及びウリカワの生育状態を各々肉眼観察し、０（無処理区と同等）～１００（完全枯殺）の生育抑制率（％）で評価し、第７表の結果を得た。 On the 13th to 15th days after the chemical treatment, the growth conditions of Tainubie, Firefly and Urikawa were observed with the naked eye, and evaluated with a growth inhibition rate (%) of 0 (equivalent to the untreated group) to 100 (completely killed), The results in Table 7 were obtained.
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000067
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000068
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000069
Figure JPOXMLDOC01-appb-T000070
Figure JPOXMLDOC01-appb-T000070
　次に、本発明の製剤例を記載する。
　製剤例１
（１）本発明に係る化合物　　　　　　　　　　　　　　　　７５　　　重量部
（２）ゲロポンＴ－７７（商品名；ローヌ・プーラン社製）　１４．５　重量部
（３）ＮａＣｌ　　　　　　　　　　　　　　　　　　　　　１０　　　重量部
（４）デキストリン　　　　　　　　　　　　　　　　　　　　０．５　重量部
以上の（１）～（４）の各成分を高速混合細粒機に入れ、さらにそこへ２０重量％の水を加え造粒、乾燥することにより顆粒水和剤が得られる。 Next, formulation examples of the present invention will be described.
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 The components (1) to (4) are put into a high-speed mixing fine granulator, 20% by weight of water is further added thereto, and granulated and dried to obtain a granulated wettable powder.
　製剤例２
（１）カオリン　　　　　　　　　　　　　　　　　　　　　７８　重量部
（２）ラベリンＦＡＮ（商品名；第一工業製薬（株）製）　　　２　重量部
（３）ソルポール５０３９（商品名；東邦化学工業（株）製）　５　重量部
（４）カープレックス（商品名；ＤＳＬジャパン（株）製）　１５　重量部
以上の（１）～（４）の成分の混合物と本発明に係る化合物とを９：１の重量割合で混合することにより水和剤が得られる。 Formulation Example 2
(1) Kaolin 78 parts by weight (2) Labelin FAN (trade name; manufactured by Daiichi Kogyo Seiyaku Co., Ltd.) 2 parts by weight (3) Solpol 5039 (trade name; manufactured by Toho Chemical Industry Co., Ltd.) 5 parts by weight (4 ) Carplex (trade name; manufactured by DSL Japan Co., Ltd.) 15 parts by weight or more of the mixture of the components (1) to (4) and the compound according to the present invention are mixed at a weight ratio of 9: 1. A Japanese medicine is obtained.
　製剤例３
（１）ハイフィラーＮｏ．１０（商品名；松村産業（株）製）　３３　重量部
（２）ソルポール５０５０（商品名；東邦化学工業（株）製）　　３　重量部
（３）ソルポール５０７３（商品名；東邦化学工業（株）製）　　４　重量部
（４）本発明に係る化合物　　　　　　　　　　　　　　　　　６０　重量部
以上の（１）～（４）の各成分を混合することにより水和剤が得られる。 Formulation Example 3
(1) High filler No. 10 (trade name; manufactured by Matsumura Sangyo Co., Ltd.) 33 parts by weight (2) Solpol 5050 (trade name; manufactured by Toho Chemical Co., Ltd.) 3 parts by weight (3) Solpol 5073 (trade name; Toho Chemical Industries, Ltd.) 4 parts by weight (4) Compound according to the present invention 60 parts by weight or more of each component (1) to (4) is mixed to obtain a wettable powder.
　製剤例４
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　　　４　　　重量部
（２）ベントナイト　　　　　　　　　　　　　　　　　　　　　３０　　　重量部
（３）炭酸カルシウム　　　　　　　　　　　　　　　　　　　　６１．５　重量部
（４）トキサノンＧＲ－３１Ａ（商品名；三洋化成工業（株）製）　３　　　重量部
（５）リグニンスルホン酸カルシウム塩　　　　　　　　　　　　　１．５　重量部
予め粉砕した（１）と、（２）及び（３）とを混合し、そこへ（４）、（５）及び水を加えて混合し、押出造粒する。その後、乾燥、整粒することにより粒剤が得られる。 Formulation Example 4
(1) Compound according to the present invention 4 parts by weight (2) Bentonite 30 parts by weight (3) Calcium carbonate 61.5 parts by weight (4) Toxanone GR-31A (trade name; manufactured by Sanyo Chemical Industries, Ltd.) 3 parts by weight (5) Calcium lignin sulfonate 1.5 parts by weight Pre-ground (1), (2) and (3) are mixed, and (4), (5) and water are added and mixed there. Extrude granulate. Then, a granule is obtained by drying and sizing.
　製剤例５
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　３０　重量部
（２）ジークライト（商品名；ジークライト（株）製）　　　　６０　重量部
（３）ニューカルゲン　ＷＧ－１（商品名；竹本油脂（株）製）　５　重量部
（４）ニューカルゲン　ＦＳ－７（商品名；竹本油脂（株）製）　５　重量部
上記（１）、（２）及び（３）を混合し、粉砕機を通した後、（４）を加えて混練後、押出造粒する。その後、乾燥、整粒することにより顆粒水和剤が得られる。 Formulation Example 5
(1) Compound according to the present invention 30 parts by weight (2) Siegrite (trade name; manufactured by Siegrite Co., Ltd.) 60 parts by weight (3) New Calgen WG-1 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 Part by weight (4) New Calgen FS-7 (trade name; manufactured by Takemoto Yushi Co., Ltd.) 5 parts by weight After mixing (1), (2) and (3) above and passing through a pulverizer, (4) After kneading and extruding granulation. Then, a granule wettable powder is obtained by drying and sizing.
　製剤例６
（１）本発明に係る化合物　　　　　　　　　　　　　　　　　　　２８　重量部
（２）ソプロポールＦＬ（商品名；ローヌ・プーラン社製）　　　　　２　重量部
（３）ソルポール３５５（商品名；東邦化学工業（株）製）　　　　　１　重量部
（４）ＩＰソルベント１６２０（商品名；出光石油化学（株）製）　３２　重量部
（５）エチレングリコール　　　　　　　　　　　　　　　　　　　　６　重量部
（６）水　　　　　　　　　　　　　　　　　　　　　　　　　　　３１　重量部
以上の（１）～（６）の各成分を混合し、湿式粉砕機（ダイノーミル）を用いて粉砕することにより水性懸濁剤が得られる。
　なお、２０１３年２月１５日に出願された日本特許出願２０１３－０２８４５３号の明細書、特許請求の範囲、及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。 Formulation Example 6
(1) Compound according to the present invention 28 parts by weight (2) Sopropol FL (trade name; manufactured by Rhône-Poulenc) 2 parts by weight (3) Solpol 355 (trade name; manufactured by Toho Chemical 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 entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2013-028453 filed on February 15, 2013 are incorporated herein as the disclosure of the specification of the present invention. Is.

Claims (5)

  1. 　式（Ｉ）：
    Figure JPOXMLDOC01-appb-C000001
     〔式（Ｉ）中、Ｒ１はＸで置換されてもよいフェニル、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－Ｃ(Ｏ)Ｒ５、－Ｃ(Ｏ)Ｒ５で置換されたＣ１‐６アルキル、－ＳＯ２－Ｒ６、－ＳＯ２－Ｒ６で置換されたＣ１‐６アルキル又は－Ｙ－Ｒ７で置換されたＣ１‐６アルキルであり；Ｒ２は水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３はＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ３‐６シクロアルキルＣ１‐６アルキル、Ｘで置換されてもよいフェニル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ４は水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ１‐６アルキルＣ３‐８シクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環又はジＣ１‐６アルキルアミノであり；Ｒ７はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル、Ｃ１‐６アルコキシカルボニル又はＣ３‐６シクロアルキルオキシカルボニルであり；ＡはＣＨ又は窒素原子であり；Ｒａ及びＲｂはそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘはハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルフィニル、Ｃ１‐６アルキルスルホニル、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６ハロアルキルチオ、Ｃ１‐６ハロアルキルスルフィニル、Ｃ１‐６ハロアルキルスルホニル、ニトロ、シアノ又はフェニルであり；Ｙは酸素原子又は硫黄原子であり；Ｗ１は酸素原子又は硫黄原子であり；Ｗ２は酸素原子又は硫黄原子であり；ｎは０、１又は２である〕で表される化合物又はその塩。     Formula (I):
    Figure JPOXMLDOC01-appb-C000001
     [In formula (I), R 1 may be substituted by X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, heterocycle which may be substituted by X, it may be substituted with X benzyl, cyano C 1-6 alkyl, -C (O) R 5, -C (O) C 1 substituted by R 5 - 6 alkyl, -SO 2 -R 6, it is substituted with -SO 2 -R 6 6 alkyl or -Y-R 7 C 1 is substituted with - - 6 is alkyl C 1 was; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 C Alkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 halocycloalkyl, phenyl optionally substituted by X, heterocycle which may be substituted by X, it may be substituted with X Benzyl, cyano C 1-6 alkyl, — (CR a R b ) n —C (O) R 5 , — (CR a R b ) n —SO 2 —R 6 or — (CR a R b ) n —Y It is a -R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 3 - 6 cycloalkyl C 1 - 6 be 6 cycloalkylalkyl, is also phenyl or C 1 substituted with X - - 6 alkoxy C 1; R 4 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl , C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 1 - 6 alkyl C 3 - 8 cycloalkyl, phenyl optionally substituted by X, naphthyl which may be substituted by X, optionally substituted with X good heterocycle, -CH 2 benzyl optionally substituted or X -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, optionally substituted with X phenyl , which may be substituted by X phenoxy, heterocycle which may be substituted with X, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - 6 alkoxy C 1 - 6 alkyl by and; R 6 is C 1 - 6 alkyl, C 1 - Ah 6 alkylamino - 6 haloalkyl, phenyl optionally substituted by X, which may heterocycle or be di C 1 substituted with X Ri; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, which may be substituted by X phenyl, C 1 - 6 alkylcarbonyl, C 1 - 6 alkoxycarbonyl or C 3 - it is a 6 cycloalkyloxycarbonyl; A is CH or a nitrogen atom; R a and R b are each independently a hydrogen atom or a C 1 - be 6 alkyl; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 alkylthio, C 1 - 6 alkylsulfinyl, C 1 - 6 alkylsulfonyl, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 haloalkylthio, C 1 - 6 haloalkylsulfinyl, 1 - 6 haloalkylsulfonyl, nitro, cyano or phenyl; Y is oxygen atom or sulfur atom; W 1 is oxygen atom or sulfur atom; W 2 is oxygen atom or sulfur atom; n is 0, Or a salt thereof.
  2. 　Ｒ１がＸで置換されてもよいフェニル、Ｃ１‐６アルキル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ２が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ１‐６ハロアルキル、Ｃ３‐６シクロアルキルＣ１‐６アルキル、Ｘで置換されてもよいフェニル又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ４がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６アルキルＣ３‐８シクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６がＣ１‐６アルキル又はＸで置換されてもよいフェニルであり；Ｒ７がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｃ１‐６アルコキシＣ１‐６アルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル、Ｃ１‐６アルコキシカルボニル又はＣ３‐６シクロアルキルオキシカルボニルであり；ＡがＣＨ又は窒素原子であり；Ｒａ及びＲｂがそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘがハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルフィニル、Ｃ１‐６アルキルスルホニル、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６ハロアルキルチオ、ニトロ又はシアノであり；Ｙが酸素原子又は硫黄原子であり；Ｗ１が酸素原子であり；Ｗ２が酸素原子又は硫黄原子であり；ｎが０、１又は２である前記請求項１に記載の化合物又はその塩。 R 1 is optionally substituted with X phenyl, C 1 - 6 alkyl or C 1 - 6 alkoxy C 1 - 6 is alkyl; R 2 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, which may be benzyl substituted by X, cyano C 1-6 alkyl, - (CR a R b) n -C (O) R 5, - (CR a R b) n -SO 2 -R 6 or - (CR a R b) be n -Y-R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 1 - 6 haloalkyl, C 3 - 6 cycloalkyl alkyl C 1 - 6 alkyl, phenyl or optionally substituted with X C 1 - 6 alkoxy C 1 - 6 is alkyl; R 4 is C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl alkyl, C 1 - 6 alkyl C 3 - 8 cycloalkyl, phenyl optionally substituted by X, naphthyl which may be substituted with X, heterocycle which may be substituted with X, good benzyl or -CH be substituted with X 2 -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, which may be substituted by X phenoxy, substituted by X substituted with alkyl or X - R 6 is C 1; which may heterocycle, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - - 6 alkoxy C 1 6 is alkyl by be phenyl optionally; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, C 1 - 6 alkoxy C 1 - 6 alkyl, phenyl optionally substituted by X, C 1 - 6 Le Kill carbonyl, C 1 - 6 alkoxycarbonyl or C 3 - 6 cycloalkyl alkyloxycarbonyl; A is CH or a nitrogen atom; and R a and R b are each independently a hydrogen atom or a C 1 - 6 alkyl There; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 alkylthio, C 1 - 6 alkylsulfinyl, C 1 - 6 alkyl sulfonyl, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 haloalkylthio, a nitro or cyano; Y is oxygen atom or sulfur atom; W 1 is oxygen atom; W 2 is oxygen The compound or a salt thereof according to claim 1, which is an atom or a sulfur atom; and n is 0, 1 or 2.
  3. 　Ｒ１がＸで置換されてもよいフェニル、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル又はＣ１‐６ハロアルキルであり；Ｒ２が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｃ２‐６ハロアルキニル、Ｃ３‐６ハロシクロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル、シアノＣ１－６アルキル、－(ＣＲａＲｂ)ｎ－Ｃ(Ｏ)Ｒ５、－(ＣＲａＲｂ)ｎ－ＳＯ２－Ｒ６又は－(ＣＲａＲｂ)ｎ－Ｙ－Ｒ７であり；Ｒ３がＣ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６ハロアルキル又はＸで置換されてもよいフェニルであり；Ｒ４が水素原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐８シクロアルキル、Ｃ１‐６ハロアルキル、Ｃ２‐６ハロアルケニル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいナフチル、Ｘで置換されてもよいヘテロ環、Ｘで置換されてもよいベンジル又は－ＣＨ２－Ｙ－Ｃ１‐６アルキルであり；Ｒ５がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいフェノキシ、Ｘで置換されてもよいヘテロ環、Ｃ１‐６アルコキシ、Ｃ１‐６アルキルチオ、ジＣ１‐６アルキルアミノ又はＣ１‐６アルコキシＣ１‐６アルキルであり；Ｒ６がＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｘで置換されてもよいヘテロ環又はジＣ１‐６アルキルアミノであり；Ｒ７はＣ１‐６アルキル、Ｃ１‐６ハロアルキル、Ｘで置換されてもよいフェニル、Ｃ１‐６アルキルカルボニル又はＣ１‐６アルコキシカルボニルであり；ＡがＣＨ又は窒素原子であり；Ｒａ及びＲｂがそれぞれ独立して、水素原子又はＣ１‐６アルキルであり；Ｘがハロゲン原子、Ｃ１‐６アルキル、Ｃ２‐６アルケニル、Ｃ２‐６アルキニル、Ｃ３‐６シクロアルキル、Ｃ１‐６アルコキシ、Ｃ１‐６ハロアルキル、Ｃ１‐６ハロアルコキシ、Ｃ１‐６アルキルチオ、Ｃ１‐６アルキルスルホニル、ニトロ、シアノ又はフェニルであり；Ｙが酸素原子又は硫黄原子であり；Ｗ１が酸素原子又は硫黄原子であり；Ｗ２が酸素原子又は硫黄原子であり；ｎが０又は１である前記請求項１に記載の化合物又はその塩。 R 1 is optionally substituted with X phenyl, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl or C 1 - 6 haloalkyl; R 2 is a hydrogen atom , C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, C 2 - 6 haloalkynyl, C 3 - 6 Halocycloalkyl, phenyl optionally substituted with X, heterocycle optionally substituted with X, benzyl optionally substituted with X, cyano C 1-6 alkyl, — (CR a R b ) n —C ( O) R 5, - (CR a R b) n -SO 2 -R 6 or - (Yes in CR a R b) n -Y- R 7; R 3 is C 1 - 6 alkyl, C 2 - 6 alkenyl , C 2 - 6 alkynyl C 3 - 6 cycloalkyl, C 1 - 6 haloalkyl or there is substituted with also phenyl with X; R 4 is a hydrogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 8 cycloalkyl, C 1 - 6 haloalkyl, C 2 - 6 haloalkenyl, phenyl optionally substituted by X, which may be naphthyl substituted with X, which may be heterocyclic substituted with X, is substituted with X also good benzyl or -CH 2 -Y-C 1 - 6 is alkyl; R 5 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, may be substituted with X phenoxy, heterocycle which may be substituted with X, C 1 - 6 alkoxy, C 1 - 6 alkylthio, di C 1 - 6 alkylamino or C 1 - 6 alkoxy C 1 - 6 alkyl There; R 6 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, di is heterocycle which may be or substituted with X C 1 - 6 alkylamino; R 7 is C 1 - 6 alkyl, C 1 - 6 haloalkyl, phenyl optionally substituted by X, C 1 - 6 alkylcarbonyl or C 1 - be 6 alkoxycarbonyl; A is CH or a nitrogen atom; R a and R b There each independently a hydrogen atom or a C 1 - 6 is alkyl; X is a halogen atom, C 1 - 6 alkyl, C 2 - 6 alkenyl, C 2 - 6 alkynyl, C 3 - 6 cycloalkyl, C 1 - 6 alkoxy, C 1 - 6 haloalkyl, C 1 - 6 haloalkoxy, C 1 - 6 alkylthio, C 1 - 6 alkylsulfonyl, nitro, cyano or phenyl Ri; Y is oxygen atom or sulfur atom; W 1 is oxygen atom or sulfur atom; W 2 is oxygen atom or sulfur atom; n is A compound according to claim 1 is 0 or 1, or Its salt.
  4. 　請求項１、２又は３に記載の化合物又はその塩を有効成分として含有する除草剤。 A herbicide containing the compound or salt thereof according to claim 1, 2 or 3 as an active ingredient.
  5. 　請求項１、２又は３に記載の化合物又はその塩の除草有効量を望ましくない植物又はそれが生育する場所に施用し、望ましくない植物を防除又はその生育を抑制する方法。 A method for controlling or inhibiting the growth of an undesirable plant by applying a herbicidally effective amount of the compound or salt thereof according to claim 1, 2 or 3 to the undesired plant or a place where it grows.
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