WO2019065283A1 - Composé de pyridazinone ou sel de celui-ci, et herbicide le contenant - Google Patents

Composé de pyridazinone ou sel de celui-ci, et herbicide le contenant Download PDF

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WO2019065283A1
WO2019065283A1 PCT/JP2018/034059 JP2018034059W WO2019065283A1 WO 2019065283 A1 WO2019065283 A1 WO 2019065283A1 JP 2018034059 W JP2018034059 W JP 2018034059W WO 2019065283 A1 WO2019065283 A1 WO 2019065283A1
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alkyl
substituted
compound
formula
salt
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寿彦 植木
龍 山田
達哉 大北
幸子 ▲高▼見
中村　将之
久樹 田中
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石原産業株式会社
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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 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
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

Definitions

  • the present invention relates to pyridazinone compounds or salts thereof. More specifically, the present invention relates to novel pyridazinone compounds or salts thereof useful as active ingredients of herbicides, herbicides containing them, and control methods using them.
  • Patent Document 1 describes pyridazinone compounds having a specific chemical structure.
  • the compound has an —O—A group at the 4-position of the benzene ring substituted on the pyridazinone ring, and the chemical structure is different from that of the compound of the present invention.
  • Patent Document 2 describes a heteroaromatic ring compound having a specific chemical structure.
  • the compound is different from the compound of the present invention in that there is no pyridazinone ring in the substituent at the meta position of the phenyl ring (substituents R 3 and R 4 in Patent Document 2) to which a pyridine ring is bonded via L 1 .
  • Patent Document 3 describes pyridazinone compounds having a specific chemical structure.
  • the compound has a phenyl group or a heteroaromatic ring group directly linked to the substituent G (benzene ring) of the pyridazinone ring, and has a chemical structure different from that of the compound of the present invention.
  • Patent Document 4 describes pyridazinone compounds having a certain chemical structure.
  • the substituent corresponding to the substituent Q in the general formula (I) of the present invention (substituent R 1 in Patent Document 4) is a NR 10 R 11 group or a heterocycloalkyl ring group, and the present invention
  • the chemical structure is different from the compound of
  • An object of the present invention is to find a herbicide that exhibits excellent herbicidal performance against undesirable plants in order to save labor of controlling undesirable plants and to improve productivity of agricultural and horticultural crops.
  • the present invention provides a pyridazinone compound represented by the following general formula (I) or a salt thereof.
  • X is -O-, -S-, -SO-, -SO 2 -or -N (Y)-;
  • Q is aryl optionally substituted with Z 1 ;
  • Y is a hydrogen atom or alkyl;
  • R 1 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, haloalkyl, Z 1 in which may be substituted monocyclic aryl, optionally substituted monocyclic aryl alkyl Z 1, alkylthioalkyl, alkylsulfinyl Alkyl, alkylsulfonylalkyl, dialkylaminoalkyl, alkoxyalkyl, amino, nitro, alkylcarbonylalkyl, alkoxycarbonylalkyl or hydroxycarbonylalkyl;
  • R 2 is a hydrogen atom, alkyl, haloalkyl, cycloalkyl, hal
  • the present invention also applies a herbicide containing the pyridazinone compound of the general formula (I) or a salt thereof as an active ingredient, and a herbicidally effective amount of the compound or a salt thereof to undesired plants or places where they grow. And a method of controlling undesirable plants or suppressing their growth.
  • pyridazinone compound of the general formula (I) of the present invention or a salt thereof, significant improvement of herbicidal activity to undesired plants (weeds) can be realized as compared to similar conventional compounds. It has high safety for crops.
  • each atom of fluorine, chlorine, bromine or iodine may be mentioned.
  • the number of halogen atoms as a substituent may be one or more, and in the case of two or more, each halogen atom may be the same or different.
  • the substitution position of the halogen atom may be any position.
  • the alkyl or alkyl moiety in the general formula (I) is, for example, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl And linear or branched C 1 -C 12 groups such as decyl, undecyl and dodecyl.
  • alkoxy or alkoxy moiety in the general formula (I) is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, iso-butoxy, sec-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, Examples include linear or branched C 1 -C 12 groups such as nonyloxy, decyloxy, undecyloxy, dodecyloxy.
  • the alkenyl or alkenyl moiety in the general formula (I) is, for example, vinyl, 1-propenyl, 2-propenyl, isopropenyl, 2-methyl-1-propenyl, 1-methyl-1-propenyl, 2-methyl-2-propenyl Propenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-hexenyl, A linear or branched C 2 -C 6 group such as 2,3-dimethyl-2-butenyl may be mentioned.
  • the alkynyl or alkynyl moiety in the general formula (I) is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-methyl-3 And linear or branched C 2 -C 6 groups such as -butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl and 5-hexynyl.
  • the cycloalkyl or cycloalkyl moiety in the general formula (I) includes, for example, a C 3 -C 7 group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • a C 3 -C 7 group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
  • the cycloalkoxy or cycloalkoxy moiety in the general formula (I) includes, for example, a C 3 -C 7 group such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy.
  • the cycloalkenyl or cycloalkenyl moiety in the general formula (I) is, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, bicyclo [2.2.1] hepta-2 And C 3 -C 7 groups such as 5-dienyl.
  • Examples of the aryl in the general formula (I) include monocyclic aryl, monocyclic heteroaryl, bicyclic aryl and bicyclic heteroaryl.
  • Monocyclic aryl includes, for example, phenyl.
  • the monocyclic heteroaryl is, for example, a 5- to 6-membered heteroaryl containing 1 to 4 O, S or N.
  • Specific examples include thienyl, furyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl 1,3,4-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1 2,3-thiadiazolyl, 1,2,3,4-tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, imidazolinyl, imidazolidinyl, pyrazolinyl, pyrazolidiny
  • bicyclic aryl examples include naphthyl and indenyl.
  • the bicyclic heteroaryl includes, for example, a fused cyclic heteroaryl of a ring derived from the monocyclic heteroaryl and a ring derived from a benzene ring or the monocyclic heteroaryl.
  • Specific examples include benzothienyl, benzofuryl, indolyl, benzothiazolyl, benzoimidazolyl, benzoisoxazolyl, benzoisothiazolyl, indazolyl, benzoxazolyl, quinolyl, isoquinolyl, quinoxalinyl, phthalazinyl, cinnolinyl, quinazolinyl, naphthyridinyl, pyridopyrimidyl, Pyridopyrazinyl, imidazolo pyridyl, thiazolo pyridyl, pyrazolo pyrimidyl, imidazolo pyrazinyl, imidazol
  • nonaromatic heterocyclyl in the general formula (I) examples include monocyclic or polycyclic nonaromatic heterocyclyl containing 1 to 4 O, S or N.
  • Polycyclic non-aromatic heterocyclyl includes fused cyclic heterocyclyl, bridged heterocyclyl, or spirocyclic heterocyclyl.
  • oxo group O
  • the ring atom C, O, S or N
  • Examples of monocyclic nonaromatic heterocyclyl include oxiranyl, thiiranyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, dihydrofuryl, tetrahydrofuryl, dihydrothiophenyl, tetrahydrothiophenyl, pyrrolinyl, pyrrolidinyl, dioxolyl, dioxolanyl, dithiolanyl, Oxathiolanyl, imidazolinyl, imidazolidinyl, pyrazolinyl, pyrazolidinyl, oxazolinyl, oxazolidinyl, isoxazolinyl, isoxazolinyl, thiazolinyl, thiazolidinyl, isothiazolinyl, isothiazolidinyl, tetrahydropyranyl, dihydrothi
  • the polycyclic nonaromatic heterocyclyl includes a fused cyclic, bridged or spirocyclic nonaromatic heterocyclyl derived from the above-mentioned monocyclic nonaromatic heterocyclyl.
  • Specific examples thereof include dihydrobenzofuranyl, dihydrobenzothienyl, indolinyl, isoindolinyl, hexahydro-1H-cyclopenta [c] furanyl, hexahydro-2H-cyclopenta [b] furanyl, tetrahydrofurodioxolyl, octahydroflopyridinyl 2-oxabicyclo [3.1.0] hexanyl, 7-oxabicyclo [4.1.0] heptanyl, 2-oxabicyclo [2.2.1] heptanyl, 7-oxabicyclo [2.2.1 Heptanyl, 7-azabicyclo [2.2.1] heptanyl, 6-oxa-2-aza
  • alkylene in the general formula (I) examples include linear C 1 -C 4 groups such as methylene, ethylene, trimethylene and tetramethylene.
  • any A 1 may be a single bond (ie, any A 1 may not be present).
  • Specific examples of L 1, binds, -A 1a -, - A 1a -O-A 1a -, - A 1a -O -, - A 1a -O-C (O) -O-A 1a -, - A 1a -O-C (O) -O-, -C (O) -A 1a- , -C (O)-, -C (O) -A 1a -O-A 1a- , -C (O) -A 1a -O-, -C (O) -O-A 1a-O-, -C (O) -O-A 1a- , -C (O) -O-A 1a- , -C (O) -O-A 1a- , -C (O) -O-A 1a- , -C (O)
  • substituted in the general formula (I) means that the number of substitutions is one or more. When the number of substitutions is two or more, each substituent may be the same or different. The substitution position of each substituent may be any position.
  • the salts of the pyridazinone compounds of the general formula (I) include all salts which are agriculturally acceptable.
  • alkali metal salts such as sodium salts and potassium salts
  • alkaline earth metal salts such as magnesium salts and calcium salts
  • amine salts such as dimethylamine salts and triethylamine salts
  • hydrochlorides, perchlorates, sulfates And inorganic acid salts such as nitrates
  • organic acid salts such as acetates and methanesulfonates.
  • the pyridazinone compounds of the general formula (I) may have isomers such as diastereoisomers and optical isomers, but the present invention includes both of each isomer and isomer mixture. In the present invention, unless stated otherwise, the isomers are described as a mixture. The present invention also includes various isomers other than the above-mentioned isomers within the scope of the common technical knowledge in the relevant technical field. Also, depending on the type of isomer, the chemical structure may be different from that of the above general formula (I), but those skilled in the art have the relationship between the chemical structure and the general formula (I) and isomer. It is obvious that it is within the scope of the present invention, as it is sufficiently recognizable.
  • the pyridazinone compound of the general formula (I) or a salt thereof (hereinafter referred to as the compound of the present invention) can be produced according to the following production methods, methods for producing known salts or synthesis examples described later.
  • the method of obtaining is not limited to these methods.
  • the compound of the present invention can be produced by reacting the compound of formula (II) with the compound of formula (III) in the presence of a base.
  • T is each atom of chlorine, bromine or iodine, and the meanings of the other symbols are as described above.
  • organic bases such as a triethylamine and a pyridine, are mentioned, for example.
  • the amount of the base to be used is generally 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (II).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include ethers such as diethyl ether, dioxane, tetrahydrofuran (THF), dimethoxyethane and the like, or a mixed solvent thereof.
  • the amount of the compound of formula (III) used in this reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (II).
  • the reaction temperature of this reaction is usually -30 to 180 ° C, preferably -10 to 80 ° C.
  • the reaction time of this reaction is usually 10 minutes to 30 hours.
  • the compound of the formula (I) and the compound of the formula (IV) which is an isomer thereof or a mixture thereof may be formed.
  • the reaction mixture obtained by this reaction is mixed with, for example, water, extracted with an organic solvent, and the obtained organic layer is dried and concentrated, and then the procedure such as purification by silica gel column chromatography is performed to obtain the formula Compounds of (I) can be isolated.
  • the compound of the formula (Ia) of the present invention is a compound of the formula (II) and the compound of the formula (V) or a salt thereof in a solvent or without solvent, if necessary using a base and a condensing agent If necessary, it can be produced by reacting in the presence of additives.
  • R 4a is heterocyclyl non-aromatic may be substituted with Z 2, is a cycloalkyl substituted with good cycloalkenyl or Z 2 may be substituted with Z 2, the meanings of other symbols previously described As it is.
  • Examples of the base used for this reaction include organic bases such as triethylamine, pyridine and 4- (dimethylamino) pyridine, and inorganic bases such as potassium carbonate and sodium carbonate.
  • organic bases such as triethylamine, pyridine and 4- (dimethylamino) pyridine
  • inorganic bases such as potassium carbonate and sodium carbonate.
  • the amount of the base to be used is generally 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (II).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include polar solvents such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolinone, diethyl ether, dioxane, tetrahydrofuran (THF), dimethoxyethane And aromatic hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride and 1,2-dichloroethane, and aliphatics such as n-pentane and n-hexane Hydrocarbons or mixed solvents thereof are mentioned.
  • the amount of the compound of formula (V) used in this reaction is usually 0.5 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (II).
  • condensing agent used for this reaction for example, 1H-benzotriazol-1-yloxy tris (dimethylamino) phosphonium hexafluorophosphate, N, N′-dicyclohexylcarbodiimide, 1- (3-dimethylaminopropyl) -3 And -ethylcarbodiimide hydrochloride, 2-chloro-1-methylpyridinium iodide and the like.
  • the amount of the condensing agent to be used is generally 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (II).
  • Examples of the additive used in this reaction include 3H- [1,2,3] triazolo [4,5-b] pyridin-3-ol, 1-hydroxybenzotriazole and the like.
  • the amount of the additive to be used is generally 0.1 to 10 molar equivalents, preferably 0.1 to 3 molar equivalents, relative to the compound of formula (II).
  • the reaction temperature of this reaction is usually -30 to 180 ° C, preferably -10 to 80 ° C.
  • the reaction time of this reaction is usually 10 minutes to 30 hours.
  • a compound of formula (Ia) and a compound of formula (IVa) which is an isomer thereof or a mixture thereof may be formed.
  • the reaction mixture obtained by this reaction is mixed with, for example, water, extracted with an organic solvent, and the obtained organic layer is dried and concentrated, and then the procedure such as purification by silica gel column chromatography is performed to obtain the formula
  • the compound of (Ia) can be isolated.
  • the compound of the formula (III) in production method 1 and the compound of the formula (V) in production method 2 are known compounds or can be produced from known compounds by known methods.
  • the compound of formula (II) in production method 1 or 2 can be produced by reacting the compound of formula (VI) with morpholine.
  • R 9 is alkyl or monocyclic arylalkyl which may be substituted (eg, C 1-3 alkyl, benzyl, 4-methoxybenzyl and the like), and the meanings of other symbols are as described above.
  • the amount of morpholine used in this reaction is usually 1 to 20 molar equivalents relative to the compound of formula (VI).
  • the reaction temperature of this reaction is usually 30 to 180 ° C., preferably 50 to 130 ° C.
  • the reaction time of this reaction is usually 10 minutes to 30 hours.
  • this reaction can be performed under microwave irradiation, in which case the reaction may be promoted. After completion of this reaction, for example, the reaction mixture is mixed with water, acidified with acid, and extracted with an organic solvent, and the obtained organic layer is dried and concentrated, and purification by silica gel column chromatography, etc.
  • the compound of formula (II) can be isolated by the operation of
  • the compound of the formula (II) can be produced, for example, according to the method described in Heterocycles, 26: 1 to 4 (1987) or the like or a method according thereto.
  • the compound of formula (VI) can be produced by reacting the compound of formula (VII) with the compound of formula (VIII) in the presence of a base or a catalyst.
  • the meaning of each symbol is as described above.
  • Examples of the base used in this reaction include metal alkoxides such as potassium tert-butoxide; and inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride.
  • the amount of the base to be used is generally 1 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (VII).
  • a catalyst used for this reaction for example, palladium (II) acetate, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride and the like Palladium catalysts; and copper catalysts such as copper chloride and copper iodide.
  • the amount of the catalyst used is usually 0.001 to 0.5 molar equivalents, preferably 0.01 to 0.2 molar equivalents, relative to the compound of the formula (VII).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, dioxane, THF and dimethoxyethane; dimethylformamide (DMF) and the like Amides; sulfoxides such as dimethyl sulfoxide (DMSO); nitriles such as acetonitrile; ketones such as acetone; or mixed solvents of these.
  • the amount of the compound of formula (VIII) used in this reaction is usually 0.5 to 3 molar equivalents, preferably 1 to 2 molar equivalents, relative to the compound of formula (VII).
  • the reaction temperature of this reaction is usually 0 to 200 ° C., preferably 20 to 100 ° C.
  • the reaction time of this reaction is usually 10 minutes to 30 hours.
  • acid is added to the reaction mixture for neutralization, mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification by silica gel column chromatography, etc. By operation, the compound of formula (VI) can be isolated.
  • Compounds of formula (VIII) are known compounds or can be prepared from known compounds by known methods.
  • the compound of formula (VII) can be produced by reacting the compound of formula (IX) with an acid.
  • R 10 is optionally substituted monocyclic arylalkyl (eg, benzyl, 4-methoxybenzyl etc.), and the meanings of the other symbols are as described above.
  • a trifluoroacetic acid is mentioned, for example.
  • the amount of the acid used is usually 1 to 20 molar equivalents relative to the compound of formula (IX).
  • the reaction is carried out in the presence of a solvent, if necessary.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include organic acids such as acetic acid and propionic acid; water; and mixed solvents thereof.
  • the reaction temperature of this reaction is usually 30 to 180 ° C., preferably 50 to 130 ° C.
  • reaction time of this reaction is usually 10 minutes to 30 hours. After completion of this reaction, for example, the reaction mixture is mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification such as silica gel column chromatography is performed to obtain the compound of the formula (VII Can be isolated.
  • the compound of the formula (IX) can be produced by reacting the compound of the formula (X) with the compound of the formula (XI) or the formula (XII) in the presence of a base and a catalyst.
  • inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, a cesium carbonate, potassium phosphate, etc. are mentioned, for example.
  • the amount of the base to be used is generally 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (X).
  • a catalyst used for this reaction for example, palladium (II) acetate, tetrakis (triphenylphosphine) palladium, tris (dibenzylideneacetone) dipalladium, [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride and the like And palladium catalysts.
  • the amount of the catalyst used is usually 0.001 to 0.5 molar equivalents, preferably 0.01 to 0.2 molar equivalents, relative to the compound of the formula (X).
  • a phase transfer catalyst may be used as the catalyst.
  • phase transfer catalyst used in the present reaction examples include quaternary alkyl ammonium salts such as tetrabutyl ammonium bromide and tetrabutyl ammonium chloride.
  • the amount of the phase transfer catalyst to be used is generally 0.001 to 1.0 molar equivalents, preferably 0.01 to 0.7 molar equivalents, relative to the compound of formula (X).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane Acetone, ketones such as methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or mixed solvents of these.
  • aromatic hydrocarbons such as benzene and toluene
  • alcohols such as methanol, ethanol and propanol
  • ethers such as diethyl ether, dioxane, THF and dimethoxyethane Acetone, ketones such as methyl ethyl ketone
  • amides such as DMF
  • sulfoxides such as DMSO
  • water or mixed solvents of these.
  • a ligand can be added as needed.
  • the amount of the ligand to be used is generally 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound of formula (X).
  • the amount of the compound of formula (XI) or the compound of formula (XII) used in this reaction is usually 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of formula (X) It is.
  • the reaction temperature of this reaction is usually 0 to 180 ° C., preferably 30 to 150 ° C.
  • the reaction time of this reaction is usually 10 minutes to 100 hours.
  • the reaction mixture is mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification such as silica gel column chromatography is performed to obtain the compound of formula (IX Can be isolated.
  • the compounds of formula (XI) are known compounds or can be prepared from known compounds by known methods.
  • Compounds of formula (X) are known compounds or can be prepared from known compounds by known methods.
  • the compound of the formula (X) can be prepared according to the method described in Journal of Heterocyclic Chemistry (J. Heterocyclic. Chem.), Vol. 33, pp. 1579-1582 (1996), or a method analogous thereto It can be manufactured.
  • the compound of the formula (XII) can be produced by reacting the compound of the formula (XIII) with the compound of the formula (XIV) in the presence of a base and a catalyst.
  • inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, a cesium carbonate, potassium phosphate, potassium acetate
  • the amount of the base to be used is generally 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (XIII).
  • palladium catalysts such as palladium (II) acetate, tetrakis (triphenyl phosphine) palladium, tris (dibenzylidene acetone) dipalladium, etc. are mentioned, for example.
  • the amount of the catalyst to be used is generally 0.001 to 0.5 molar equivalents, preferably 0.01 to 0.2 molar equivalents, relative to the compound of formula (XIII).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane Acetone, ketones such as methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or mixed solvents of these.
  • aromatic hydrocarbons such as benzene and toluene
  • alcohols such as methanol, ethanol and propanol
  • ethers such as diethyl ether, dioxane, THF and dimethoxyethane
  • Acetone ketones such as methyl ethyl ketone
  • amides such as DMF
  • sulfoxides such as DMSO
  • water or mixed solvent
  • the ligand examples include tricyclohexyl phosphine, 2-dicyclohexyl phosphino-2 ′, 6′-dimethoxybiphenyl and the like.
  • the amount of the ligand to be used is generally 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound of formula (XIII).
  • the amount of the compound of formula (XIV) to be used in this reaction is generally 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of formula (XIII).
  • the reaction temperature of this reaction is usually 0 to 180 ° C., preferably 30 to 150 ° C.
  • the reaction time of this reaction is usually 10 minutes to 100 hours.
  • this reaction can be performed under microwave irradiation, in which case the reaction may be promoted. After completion of the reaction, for example, the reaction mixture is mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification such as silica gel column chromatography is performed to obtain the compound of the formula (XII Can be isolated.
  • the compound of the formula (XIII) can be produced by reacting the compound of the formula (XVI) with the compound of the formula (XV) in the presence of a base and a catalyst.
  • a base used for this reaction For example, Inorganic bases, such as sodium carbonate, potassium carbonate, sodium hydrogencarbonate, a cesium carbonate, potassium phosphate; Organic bases, such as a triethylamine and a diisopropyl ethylamine, are mentioned.
  • the amount of the base to be used is generally 1 to 10 molar equivalents, preferably 1 to 5 molar equivalents, relative to the compound of formula (XVI).
  • palladium catalysts such as palladium (II) acetate, tetrakis (triphenyl phosphine) palladium, tris (dibenzylidene acetone) dipalladium, etc. are mentioned, for example.
  • the amount of the catalyst to be used is generally 0.001 to 0.5 molar equivalents, preferably 0.01 to 0.2 molar equivalents, relative to the compound of formula (XVI).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, for example, aromatic hydrocarbons such as benzene and toluene; alcohols such as methanol, ethanol and propanol; ethers such as diethyl ether, dioxane, THF and dimethoxyethane Acetone, ketones such as methyl ethyl ketone; amides such as DMF; sulfoxides such as DMSO; water; or mixed solvents of these.
  • aromatic hydrocarbons such as benzene and toluene
  • alcohols such as methanol, ethanol and propanol
  • ethers such as diethyl ether, dioxane, THF and dimethoxyethane
  • Acetone ketones such as methyl ethyl ketone
  • amides such as DMF
  • sulfoxides such as DMSO
  • water or mixed solvent
  • the ligand examples include tricyclohexylphosphine, 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl, 4,5-bis (diphenylphosphino) -9,9-dimethylxanthene and the like.
  • the amount of the ligand to be used is generally 0.002 to 1 molar equivalent, preferably 0.02 to 0.4 molar equivalent, relative to the compound of formula (XVI).
  • the amount of the compound of formula (XV) used in this reaction is generally 0.5 to 2 molar equivalents, preferably 1 to 1.5 molar equivalents, relative to the compound of formula (XVI).
  • the reaction temperature of this reaction is usually 0 to 180 ° C., preferably 30 to 150 ° C.
  • the reaction time of this reaction is usually 10 minutes to 100 hours. After completion of the reaction, for example, the reaction mixture is mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification such as purification by silica gel column chromatography is performed to obtain a compound of formula (XIII Can be isolated.
  • Compounds of formula (XVI) are known compounds or can be prepared from known compounds by known methods.
  • the compounds of formula (XV) are known compounds.
  • the compound of the formula (XIII) can be produced by reacting the compound of the formula (XVII) with the compound of the formula (XVIII) in the presence of a base.
  • the meaning of each symbol is as described above.
  • Examples of the base used in this reaction include metal alkoxides such as potassium tert-butoxide; and inorganic bases such as potassium carbonate, cesium carbonate and sodium hydride.
  • the amount of the base to be used is generally 1 to 10 molar equivalents, preferably 1 to 3 molar equivalents, relative to the compound of formula (XVII).
  • the reaction is usually carried out in the presence of a solvent.
  • the solvent is not particularly limited as long as it is inert to the reaction, and examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene; ethers such as diethyl ether, dioxane, THF and dimethoxyethane; amides such as DMF; And the like; sulfoxides such as acetonitrile; ketones such as acetone; and mixed solvents thereof.
  • the amount of the compound of the formula (XVIII) to be used in this reaction is usually 0.5 to 3 molar equivalents, preferably 1 to 2 molar equivalents, relative to the compound of the formula (XVII).
  • the reaction temperature of this reaction is usually 0 to 200 ° C., preferably 20 to 100 ° C.
  • the reaction time of this reaction is usually 10 minutes to 30 hours.
  • acid is added to the reaction mixture for neutralization, mixed with water, extracted with an organic solvent, the obtained organic layer is dried and concentrated, and purification by silica gel column chromatography, etc. By operation, the compound of formula (XIII) can be isolated.
  • Compounds of formula (XVII) are known compounds or can be prepared from known compounds by known methods.
  • the manufacturing method of the intermediate body used in manufacturing this invention compound is not limited to the manufacturing method of the said illustration, You may employ
  • each starting material is not limited to the above exemplified compounds, and any compound can be used as long as it can produce the compound of the present invention.
  • the compounds of the present invention can control a wide range of undesirable plants such as annual weeds 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 green foxtail (Setaria viridis L.)
  • giant foxtail giant foxtail (Setaria faberi Herrm.
  • Setaria pumila (yellow foxtail (Setaria lutescens Hubb. )), goosegrass (goosegrass (Eleusine indica L ), Oats (wild oat ( Avena fatua L.)), sorghum (johnsongrass ( Sorghum halepense L.)), larch (quackgrass ( Agropyron repens L.)), brachiaria (Signalgrass ( Brachiaria plantaginea (Link) Hitch, Brachiaria decumbens Stapf. , Brachiaria platyphylla (Groseb.
  • Leptochloa chinensis sprangletop (Leptochloa chinensis (L.) Nees)
  • Itoazegaya red sprangletop (Leptochloa panicea (Retz .) Ohwi)
  • annual bluegrass annual bluegrass (Poa annua L.)
  • Black grass Alopecurus myosuroides Huds., Alopecurus aequalis Sobol.
  • Cholorado bluestem Agropyron tsukushiense (Honda) Ohwi)
  • Shinchoniogar southern sandbur ( Cenchrus echinatus L.).
  • Gramineae such as Lolium multiflorum Lam.), Bodweed (rigid ryegrass ( Lolium rigidum Gaud.)), American sand buffalo (Cheat grass ( Bromus tectorum L.)), Oryza sativa (bermudagrass ( Cynodon dactylon Pers.)) Kagomegaatsuri (rice flatsedge ( Cyperus iria L.)), Hamasyu (purple nutsedge ( Cyperus rotundus L.)), Kihamasuge (yellow nutsedge ( Cyperus esculentus L.)), Firefly (Japanese bulrush ( Scirpus j ( Scirpus j )) uncoides)), Cyperus (flatsedge (Cyperus serotinus)), smallflower umbrellaplant (small-flower umbrellaplant (Cyperus difformis )), Eleocharis acicularis (slender spikerush (Eleocharis acicularis))
  • Amaranthaceae weeds such as; Sanaetade (pale smartweed (Polygonum lapathifolium L.) ), Harutade (ladysthumb (Polygonum persicaria L.)) , wild buckwheat (wild buckwheat (Polygonum convolvulus L.)), Scutulata weeds (polygonaceae) such as knotweed ( Polygonum aviculare L.); Scutellariata (flexuous bittercress ( Cardamine flexuosa WITH.)), Pheasant (shepherd's-purse ( Capsella bursapastoris Medik.)), Cruciferous weeds (cruciferae), such as the mustard (indian mustard ( Brassica juncea Czern.)); Marva asagao (tall morningglory ( Ipomoea purpur
  • the compounds of the present invention are useful crops such as corn (Zea mays L.), soybean (Glycine max (L.) Merrill), cotton (cotton (Gossypium spp.)), Wheat (wheat (w) Triticum aestivum (L.) Thell., Rice (Oryza sativa L.), barley (barley (Hordeum vulgare L.)), rye (rye (Secale cereale L.)), oat (oven (Avena sativa L)) ), Sorghum (sorghum (Sorghum spp.)), Rape (rape (Brassica rapa L.)), rapeseed (rapeseed (Brassica napus L.)), sunflower (sunflower (Helianthus annuus L.)), sugar beet (sugar) beet (Beta vulgaris L.
  • the herbicidal composition of the present invention is preferably used in places where useful crops such as grass, soybean, cotton, wheat, rice, corn, rape, rape, sunflower, sugar beet, sugar cane, peanuts, flax, tobacco, etc. used.
  • HPPD inhibitors such as isoxaflutol
  • ALS inhibitors such as imazethapyr and thifensulfuron methyl
  • EPSP synthetase inhibitors such as glyphosate
  • glutamine synthetase inhibitors such as glufosinate, cetoxim etc
  • Plants that have been conferred, by classical breeding methods, resistance to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba and 2,4-D.
  • corn and canola varieties resistant to imidazolinone herbicides (trade name: Clearfield TM); STS soybean resistant to sulfonylurea ALS inhibitory herbicides; and the like.
  • Useful crops in the present invention also include transformed plants produced by genetic recombination technology.
  • Examples of transformed plants include herbicide-resistant transformed plants, pest-resistant transformed plants, transformed plants for plant components, and plant pathogen-resistant transformed plants.
  • useful crops of the present invention also include stack varieties combining these multiple useful traits.
  • the herbicidal composition of the present invention is effective in selectively controlling undesirable plants or suppressing their growth in cultivation of various transformed plants (for example, soybean, cotton, rapeseed, corn etc.) of the above-mentioned useful crops. It can be used.
  • Herbicide-resistant transformed plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron methyl, EPSP synthetase inhibitors such as glyphosate, and glutamine synthetase inhibitors such as glufosinate, Included are plants that have been rendered resistant to acetyl CoA carboxylase inhibitors such as cetoxidim and to herbicides such as bromoxynil, dicamba, 2,4-D and the like.
  • Examples of pest-resistant transformed plants include plants that have become capable of synthesizing toxins and the like known in the genus Bacillus.
  • the toxins synthesized by these transformed plants in particular confer to the plants resistance to beetle pests, hemiptera pests, dipteran pests, lepidopteran pests and nematodes.
  • such toxins include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab, and hybrid toxins of insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A, Also included are truncated toxins and modified toxins.
  • transformed plants relating to plant components include plants to which oil component modification, amino acid content enhancement traits and the like have been imparted.
  • Plant pathogen resistant transformed plants include plants which have been given the ability to produce anti-pathogenic substances with selective action.
  • Specific transformed plants are not particularly limited.
  • maize glyphosate resistant, soybean, cotton, rapeseed and sugar beet (trade name: RoundupReady TM, Agrisure TM, Gly -Tol TM); maize which is resistant to glufosinate, soybean, cotton and rapeseed cultivars (trade name: LibertyLink TM); glyphosate and soybean and cotton varieties resistant to dicamba (trade name: RoundupReady 2 Xtend TM); glyphosate and 2,4-D soybean resistant to, cotton and maize varieties (trade name: Enlist TM); glyphosate , glufosinate and dicamba tolerant and is cotton cultivar (trade name: Bollgard II TM XtendFlex TM); bromoxynil resistant cotton varieties (trade name: BXN); glyphosate Maize resistant to both over preparative and ALS inhibitors, soybean varieties (trade name: Optimum TM, GAT TM); varieties resistant to imid
  • the compound of the present invention is usually mixed with various agricultural adjuvants to form powders, granules, water dispersible granules, water dispersible granules, tablets, pills, capsules (including forms to be packaged with a water-soluble film), It can be formulated and applied in various forms such as aqueous suspensions, oily suspensions, microemulsions, suspoemulsions, aqueous solvents, emulsions, solutions, pastes, etc., but for the purpose of the present invention As long as it is compatible, it can be in any conventional formulation used in the art.
  • Adjuvants used in the preparation include solid supports such as diatomaceous earth, calcium hydroxide, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch, etc .; Toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, solvents such as alcohol; fatty acid salt, benzoate, Alkyl sulfosuccinates, dialkyl sulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkyl aryl sulfates, alkyl diglycol
  • adjuvants can be appropriately selected and used alone or in combination without departing from the object of the present invention.
  • various adjuvants usually used such as an extender, a thickener, an antisettling agent, an antifreeze, a dispersion stabilizer, a safener, a mildew inhibitor, a foaming agent, a disintegrant, a binder and the like are also used. can do.
  • the weight ratio of the compound of the present invention to the various adjuvants described above is usually 0.1: 99.9 to 95: 5, preferably 0.2: 99.8 to 85:15.
  • the compounding method of this invention compound and various adjuvants is not specifically limited, According to a well-known method, it can mix
  • the application amount (herbicidal effective amount) of the herbicide containing the compound of the present invention can not be generally defined by the difference in weather conditions, soil conditions, formulation form, type of undesired plants to be targeted, application time, etc., 1 hectare
  • the application amount of the compound of the present invention (hereinafter also referred to as the active ingredient amount) is preferably 0.1 to 5,000 g, more preferably 0.5 to 3,000 g, still more preferably 1 to 1,000 g, particularly preferably 10 to 500 g. Apply.
  • the present invention also includes methods of controlling undesired plants by application of such herbicides.
  • the herbicide containing the compound of the present invention may be used alone or in combination or in combination with other pesticides, fertilizers, safeners and the like. In the case of combined use or combined use, it may show more excellent effect and action.
  • Other pesticides include herbicides, fungicides, antibiotics, plant hormones, insecticides and the like.
  • a mixed herbicidal composition in which the compound of the present invention and one or more compounds which are active ingredients of other herbicides are used in combination or in combination has a range of applicable herb species, time of drug treatment, herbicidal activity Etc. can be improved in the preferred direction.
  • the compounds of the present invention and the compounds which are active ingredients of other herbicides may be separately formulated and mixed at the time of spraying, or both may be formulated and used together.
  • the present invention also includes the mixed herbicidal composition.
  • the mixing ratio of the compound of the present invention to the compound which is an active ingredient of another herbicide can not be generally defined depending on the difference in weather conditions, soil conditions, formulation of the drug, application time, application method and the like, the compound 1 of the present invention
  • the other herbicide is preferably compounded in an amount of 0.001 to 10,000 parts by weight, and more preferably 0.01 to 1,000 parts by weight, per compound of the active ingredient.
  • the application amount is 0.1 to 10,000 g, preferably 0.2 to 5,000 g, more preferably 10 to 3,000 g of the total amount of the active ingredient per hectare.
  • the present invention also includes a method of controlling undesired plants by applying such a mixed herbicidal composition.
  • Quaternary ammonium salt-based compounds such as paraquat and diquat, which are considered to be free radicals in plants themselves and to generate active oxygen to exhibit rapid herbicidal efficacy.
  • Diphenyl ether compounds such as oxyfluorfen (oxyfluorfen), lactofen (lactofen), acronifene (aclonifen), ethoxyphen-ethyl (ethoxyfen-ethyl), fluoroglycofen-ethyl (fluoroglycofen-ethyl), fluoroglycofen (fluoroglycofen); Chlorphthalim, chlormiphthalzin, flumioxazine, flumiclorac, flumiclorac-pentyl, cinidon-ethyl, fluthiacet-methyl, EK
  • Pyridazinone compounds such as norflurazon (norflurazon), chloridazon (chloridazon), metflurazon (metflurazon);
  • Pyrasulfotole pyrazole compounds such as tolpyralate) or amitrole (amitrole), fluridone (fluridone), flurtamone (flurtamone), diflufenican (diflufenican), methoxyphenone (methoxyphenone), chromazone (clomazone), sulcoto Rion (sulcotrione), mesotrione (mesotrione), tembotrione (tembotrione), tefuryltrione (tefuryltrione), fenquinotrione (fenquinotrione), lancotrione (lancotrione), cyclopyrimorate (cyclopyri) morate, isoxaflutole, diphenzoquat, difenzoquat-metilsulfate,
  • chlorimuron ethyl chlorimuron-ethyl
  • chlorimuron chlorimuron
  • sulfometuron methyl sulfometuron-methyl
  • sulfometuron sulfometuron
  • primisulfuron methyl primaryisulfuron-methyl
  • primisulfuron primaryisulfuron
  • Bensulfuron methyl butsulfuron-methyl
  • chlorsulfuron (chlorsulfuron) methsulfuron methyl (metsulfuron-methyl), methsulfuron (metsulfuron), cinurosulfuron (cinosulfuron)
  • pyrazosulfuron ethyl pyrazosulfuron-ethyl
  • Pyrazosulfuron flazasulfuron (flazasulfuron)
  • rimsulfuron rimsulfuron
  • 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) Are said to show herbicidal efficacy.
  • One or two or more of the above-mentioned compounds which are active ingredients of other herbicides can be appropriately selected.
  • the active ingredients of other herbicides are not limited to the compounds exemplified above.
  • N, N'-dicyclohexylcarbodiimide (76 mg) was added and stirred further overnight.
  • N, N'-dicyclohexylcarbodiimide (76 mg) was added, allowed to react for 4 hours and 10 minutes, and then stirred with cooling in an ice water bath.
  • the reaction mixture is filtered, and the obtained filtrate is concentrated.
  • Ethyl acetate is added to the obtained residue, and the mixture is washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine, and the organic layer is dried over sodium sulfate. And the solvent was distilled off under reduced pressure.
  • Table 1 representative examples of the compound of the present invention are listed in Table 1. These compounds can be synthesized based on the above-mentioned synthesis example or production method.
  • Table 1 No. is compound No., Me is methyl, Et is ethyl, Pr is normal propyl, i-Pr is isopropyl, n-Bu is normal butyl, t is t -Bu is a tertiary butyl group, c-Pr is a cyclopropyl group, c-Hex is a cyclohexyl group, Ph is a phenyl group, Bn is a benzyl group, Boc is a tertiary butoxycarbonyl group, Cbz is a benzyl group Each represents an oxycarbonyl group; Further, “4,6- (Me) 2 ” in the table indicates that the methyl group is substituted at the 4- and 6-positions, respectively, and the same applies to the other similar descriptions. Also, Q in
  • Test Example 1 Upland crop soil was put in a 1 / 300,000 hectare pot and seeds of various plants were sown. After that, the plants have a fixed leaf age ((1) barnyardgrass ( Echinochloa crus-galli L.)); 1.3 to 2.7 leaf stages, (2) crabgrass (Cibgrass ( Digitaria sanguinalis L.)); 0.5 to 2.4 leaf stages (3) green foxtail ( Setaria viridis L.); 1.3 to 3.0 leaf stage, (4) oats (wild oat ( Avena fatua L.)); 0.7 to 1.2 leaf stage, (5) oat ryegrass (italian ryegrass) ( Lolium multiflorum Lam.)); When reaching the leaf stage of 0.7 to 1.6, a wettable powder or emulsion prepared by applying the compound of the present invention according to a conventional formulation method is shown in Table 3 for each of the present compounds of the present invention.
  • Test example 2 Upland field soil is filled in 1 / 300,000 hectare pots, and various plants ((Bernyardgrass ( Echinochloa crus-galli L.)), crabgrass (Crabgrass ( Digitaria sanguinalis L.)), Enoclogosa (green foxtail ( Setaria viridis L.))
  • a wettable powder or emulsion prepared by applying the compound of the present invention according to a conventional formulation method, and the amount of each of the predetermined active ingredients (gai / ha) of the compound of the present invention shown in Table 4.
  • the mixture was weighed, diluted to 1000 liters of water per hectare, and treated with soil with a small spray. After the soil treatment, the growth state of various plants was visually observed on the 14th day, and the herbicidal effect was evaluated at a growth inhibition rate (%) of 0 (equivalent to the untreated area) to 100 (complete death). The results are shown in Table 4.
  • Formulation example 1 (1) the compound of the present invention 75 parts by weight (2) sodium alkylbenzene sulfonate 14.5 parts by weight (3) NaCl 10 parts by weight (4) dextrin 0.5 parts by weight or more of each component of (1) to (4)
  • a water dispersible granule can be obtained by placing in a high speed mixing granulator, adding thereto 20% water, granulating and drying.
  • Formulation example 2 (1) kaolin clay 78 parts by weight (2) sodium alkylnaphthalene sulfonate 2 parts by weight (3) sodium polycarboxylate 5 parts by weight (4) white carbon 15 parts by weight or more of a mixture of components (1) to (4)
  • a wettable powder is obtained by mixing the compound of the present invention and the compound of the present invention in a weight ratio of 9: 1.
  • Formulation example 3 (1) clay 33 parts by weight (2) sodium naphthalene sulfonate 3 parts by weight (3) sodium lignin sulfonate 4 parts by weight (4) the compound of the present invention 60 parts by weight or more of each component of (1) to (4)
  • the wettable powder is obtained by
  • Formulation example 4 (1) the compound of the present invention 4 parts by weight (2) bentonite 30 parts by weight (3) calcium carbonate 61.5 parts by weight (4) sodium polyacrylate 3 parts by weight (5) calcium lignin sulfonate 1.5 parts by weight (1), (2) and (3) are mixed, (4), (5) and water are added thereto, mixed, and extruded and granulated. Thereafter, the granules are obtained by drying and sizing.
  • Formulation example 5 (1) the compound of the present invention 30 parts by weight (2) clay 60 parts by weight (3) sodium alkylsulfosuccinate 5 parts by weight (4) salt of alkyl naphthalene sulfonic acid formaldehyde condensate 5 parts by weight the above (1), (2), After mixing (3) and (4) and passing through a grinder, water is added and kneaded, and then extrusion granulation is carried out. Thereafter, drying and sizing are performed to obtain a water dispersible granule.
  • Formulation Example 6 (1) the compound of the present invention 20 parts by weight (2) polyoxyethylene arylphenyl ether phosphate 3 parts by weight (3) propylene glycol 8 parts by weight (4) bentonite 1 part by weight (5) water 60 parts by weight or more An aqueous suspension is obtained by mixing the components 1) to (5) and grinding using a wet grinder.
  • Formulation example 7 (1) the compound of the present invention 35 parts by weight (2) polyoxyethylene arylphenyl ether phosphate ester salt 3 parts by weight (3) a salt of an alkyl naphthalene sulfonic acid-formaldehyde condensate 2 parts by weight (4) propylene glycol 10 parts by weight (5 ) Xanthan gum 0.2 parts by weight (6) mildew proofing agent 0.1 part by weight (7) water 49.7 parts by weight or more of the components (1) to (3) and (7) are mixed, and wet mill The aqueous suspension is obtained by mixing (5), (6) and (4).
  • Formulation Example 8 (1) the compound of the present invention 10 parts by weight (2) polyoxyethylene hydrogenated castor oil 12 parts by weight (3) organic bentonite 1 part by weight (4) corn oil 77 parts by weight or more of the components (1) to (4) An oily suspension is obtained by mixing and grinding using a wet grinder.
  • Formulation Example 9 (1) the compound of the present invention 25 parts by weight (2) polyoxyethylene arylphenyl ether 10 parts by weight (3) aromatic hydrocarbon 65 parts by weight or more of the components (1) to (3) to obtain an emulsion Is obtained.
  • the pyridazinone compound according to the present invention or a salt thereof exhibits excellent herbicidal effects when used as an active ingredient of a herbicide.
  • the scope of application is diverse as non-agricultural land such as paddy field, farmland, orchard, agricultural land such as vineyard, mountain forest, agricultural road, ground, factory site etc.
  • the application method is soil treatment, stem and leaf treatment, spring water treatment etc. It can be selected.

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Abstract

L'invention concerne un nouveau composé de pyridazinone ou un sel de celui-ci utile en tant que principe actif d'un herbicide, ainsi qu'un herbicide et un procédé de contrôle l'utilisant. Le composé de pyridazinone selon l'invention est représenté par la formule générale (I) ou un sel de celui-ci. (Dans la formule, la signification de chaque symbole est telle que décrite dans la spécification.)
PCT/JP2018/034059 2017-09-27 2018-09-13 Composé de pyridazinone ou sel de celui-ci, et herbicide le contenant WO2019065283A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022229055A1 (fr) 2021-04-27 2022-11-03 Bayer Aktiengesellschaft Pyridazinones substituées, leurs sels ou n-oxydes et leur utilisation comme substances actives à action herbicide
WO2023189602A1 (fr) * 2022-03-30 2023-10-05 石原産業株式会社 Composé de pyridazinone ou sel de celui-ci et agent de lutte contre les organismes nuisibles le contenant

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JP2009084276A (ja) * 2007-09-14 2009-04-23 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
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JP2012512209A (ja) * 2008-12-19 2012-05-31 バイエル・クロップサイエンス・アーゲー 除草剤および殺虫剤として作用するフェニル置換ピリダジノン
JP2012515183A (ja) * 2009-01-15 2012-07-05 シンジェンタ リミテッド 新規の除草剤
JP2012515742A (ja) * 2009-01-22 2012-07-12 シンジェンタ リミテッド シクロペンタジオン誘導化除草剤
JP2012149044A (ja) * 2010-12-27 2012-08-09 Sumitomo Chemical Co Ltd ピリダジノン化合物、それを含有する除草剤及び有害節足動物防除剤
WO2014119770A1 (fr) * 2013-01-30 2014-08-07 住友化学株式会社 Composé pyridazinone et herbicide comprenant celui-ci
WO2016174072A1 (fr) * 2015-04-30 2016-11-03 Syngenta Participations Ag Composés herbicides
JP2017075131A (ja) * 2015-10-16 2017-04-20 石原産業株式会社 ピリダジノン系化合物又はその塩、及びそれらを含有する除草剤
WO2017170759A1 (fr) * 2016-03-30 2017-10-05 石原産業株式会社 Constituant type-pyridazinone ou son sel, et herbicide le comprenant

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008133252A (ja) * 2006-03-17 2008-06-12 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
JP2009084276A (ja) * 2007-09-14 2009-04-23 Sumitomo Chemical Co Ltd ピリダジノン化合物及びそれを含有する除草剤
JP2011507893A (ja) * 2007-12-21 2011-03-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 除草性ピリダジノン誘導体
JP2012512209A (ja) * 2008-12-19 2012-05-31 バイエル・クロップサイエンス・アーゲー 除草剤および殺虫剤として作用するフェニル置換ピリダジノン
JP2012515183A (ja) * 2009-01-15 2012-07-05 シンジェンタ リミテッド 新規の除草剤
JP2012515742A (ja) * 2009-01-22 2012-07-12 シンジェンタ リミテッド シクロペンタジオン誘導化除草剤
JP2010235603A (ja) * 2009-03-13 2010-10-21 Sumitomo Chemical Co Ltd ピリダジノン化合物及びその用途
JP2012149044A (ja) * 2010-12-27 2012-08-09 Sumitomo Chemical Co Ltd ピリダジノン化合物、それを含有する除草剤及び有害節足動物防除剤
WO2014119770A1 (fr) * 2013-01-30 2014-08-07 住友化学株式会社 Composé pyridazinone et herbicide comprenant celui-ci
WO2016174072A1 (fr) * 2015-04-30 2016-11-03 Syngenta Participations Ag Composés herbicides
JP2017075131A (ja) * 2015-10-16 2017-04-20 石原産業株式会社 ピリダジノン系化合物又はその塩、及びそれらを含有する除草剤
WO2017170759A1 (fr) * 2016-03-30 2017-10-05 石原産業株式会社 Constituant type-pyridazinone ou son sel, et herbicide le comprenant

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022229055A1 (fr) 2021-04-27 2022-11-03 Bayer Aktiengesellschaft Pyridazinones substituées, leurs sels ou n-oxydes et leur utilisation comme substances actives à action herbicide
WO2023189602A1 (fr) * 2022-03-30 2023-10-05 石原産業株式会社 Composé de pyridazinone ou sel de celui-ci et agent de lutte contre les organismes nuisibles le contenant

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