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WO2006006569A1 - Dérivé de phénylpyridine ou sel de celui-ci, herbicide contenant celui-ci comme ingrédient actif et procédé d'utilisation de celui-ci - Google Patents

Dérivé de phénylpyridine ou sel de celui-ci, herbicide contenant celui-ci comme ingrédient actif et procédé d'utilisation de celui-ci Download PDF

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Publication number
WO2006006569A1
WO2006006569A1 PCT/JP2005/012781 JP2005012781W WO2006006569A1 WO 2006006569 A1 WO2006006569 A1 WO 2006006569A1 JP 2005012781 W JP2005012781 W JP 2005012781W WO 2006006569 A1 WO2006006569 A1 WO 2006006569A1
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Prior art keywords
group
halo
alkyl
alkoxy
alkyl group
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PCT/JP2005/012781
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English (en)
Japanese (ja)
Inventor
Eiji Takizawa
Shuji Kumata
Takahiro Kiyokawa
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Nihon Nohyaku Co., Ltd.
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Publication of WO2006006569A1 publication Critical patent/WO2006006569A1/fr

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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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present invention relates to novel phenyl pyridines or salts thereof, herbicides containing these as active ingredients, and methods of using the same.
  • pyridine derivatives have herbicidal activity and plant growth-regulating action (see, for example, Patent Documents 1 to 6).
  • a pyridine carboxylate having a structure similar to that of the present invention.
  • acid amides are known to have pharmaceutical activity (e.g., see Patent Document 7-9.) with 0 tooth force
  • a benzene ring and pyridine ring directly bonded at specific positions Hue Dirubiridine carboxylic acid amides and their herbicidal activity are known to date.
  • Patent Document 1 European Patent Application Publication No. 0955300
  • Patent Document 2 Pamphlet of International Publication No. 98Z04550
  • Patent Document 3 European Patent Application Publication No. 0955292
  • Patent Document 4 Pamphlet of International Publication No.OOZ75112
  • Patent Document 5 Pamphlet of International Publication No. 01Z00580
  • Patent Document 6 Pamphlet of International Publication No.99Z28301
  • Patent Document 7 International Publication No.04Z14844 Pamphlet
  • Patent Document 8 International Publication No.04Z02948 Pamphlet
  • Patent Document 9 US Patent Application Publication No. 2004Z0077853
  • a stable supply of food is indispensable for the elimination of the food crisis accompanying the expected increase in the world population in the near future.
  • a stable food supply requires economical and efficient killing or control of weeds, which are obstacles to crop cultivation and harvesting.
  • the development of LV, herbicides and plant growth regulators is becoming increasingly important.
  • the present inventors have excellent herbicidal activity that the group of compounds having a phenol pyridine skeleton represented by the general formula (I) or salts thereof can solve the above problems. As a result, the present invention has been completed.
  • R 1 is a C-C alkyl group, a halo C-C alkyl group, a C-C alkyl group, a halo C-
  • Di-C-C alkylamino group that can be selected A substituted group having 1 to 5 substituents selected Enore group,
  • Di-C-C alkylamino group power which may be different is selected 1- to 5-substituent substituted heterocyclic C-C alkyl group or halogen atom, cyan group which may be the same or different,
  • R 2 is a hydrogen atom, C-C alkyl group, C-C alkenyl group, C-C alkynyl group, C-
  • R 1 8 2 8 1 8 Indicates a alkoxycarbonyl group.
  • R 1 and R 2 together can form a 3- to 8-membered ring containing at least one heteroatom selected from oxygen atom, sulfur atom, and nitrogen atom.
  • R 3 is a halogen atom, cyano group, nitro group, hydroxyl group, pentafluorosulfur group (one SF), C-C alkyl group, halo C-C alkyl group, C-C alkenyl group, halo C -C
  • PC-C alkoxy group C-C alkoxy carbo group, C-C alkylthio group, C-C
  • they may be the same or different.
  • R 4 is a halogen atom, a C-C alkyl group, a halo C-C alkyl group, a C-C alkenyl group.
  • PC-C alkyl sulfo group C-C alkyl carbo group, C-C alkoxy car
  • Si group, hydroxyl group, formyl group, cyano group, nitro group which may be the same or different
  • R 5 and R 6 may be the same or different hydrogen atom, C-C alkyl group or halo C- C represents an alkyl group. ) Is represented. However, R 4 is the same when there are multiple
  • two adjacent R 4 groups together can be C-C alkylene.
  • a dioxy group or a halo c -c alkylenedioxy group can be indicated.
  • X represents an oxygen atom, a sulfur atom, a group represented by NH 3 or a single bond
  • Y represents an oxygen atom or a sulfur atom
  • m represents an integer of 0 to 3
  • n represents an integer of 1 to 5
  • p represents 0 or 1;
  • halogen atom means a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • C 1 -C alkyl group means a straight chain having 1 to 8 carbon atoms, 3 carbon atoms
  • 18 represents 8 to 8 branched or alicyclic alkyl groups, for example, methyl group, ethyl group, normal propyl group, isopropyl group, cyclopropyl group, 1-methylcyclopropyl group, 2-methylsilane Chloropropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, 1,2-dimethylbutyl group, cyclobutyl group, 1-methylcyclobutyl group, cyclopropylmethyl group, normal pentyl group, neopentyl group, A cyclopentyl group,
  • Examples include 1-methylcyclopentyl group, 2-methylcyclopentyl group, normal hexyl group, cyclohexyl group, 1-methylcyclohexyl group, n-octyl group and the like.
  • halo C 1 -C alkyl group is the same or different and may be one or more halogen atoms
  • the "C 1 -C alkenyl group” is a straight chain having 2 to 8 carbon atoms and having 3 to 8 carbon atoms.
  • C 2 -C alkynyl group means a straight chain having 2 to 8 carbon atoms and having 5 to 8 carbon atoms.
  • a branched or alicyclic alkyl group is exemplified, and examples thereof include an ethur group, 2-propynyl group, 2-buturyl group, 1-methyl-2-propynyl group, 2-cyclohexynyl group and the like.
  • C 1 -C alkoxy group means a straight alkoxy group having 1 to 8 carbon atoms, 3 carbon atoms
  • ⁇ 8 branched or alicyclic alkoxy groups for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, cyclopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal Examples thereof include a pentyloxy group, an isobenzyloxy group, a neopentyloxy group, a cyclopentyloxy group, a normal hexyloxy group, and a normal octyloxy group.
  • Halo C-C alkoxy group refers to one or more halogen atoms which may be the same or different.
  • a group having 3 to 6 branched or alicyclic alkyl groups bonded to a sulfur atom for example, methylthio group, ethylthio group, normal propylthio group, isopropylthio group, cyclopropylpropyl group, normal butylthio group Secondary butylthio group, tertiary butylthio group, normal pentylthio group, isopentylthio group, neopentylthio group, cyclopentylthio group, normal hexylthio group, normaloctylthio group and the like.
  • C 1 -C alkylsulfier group means a straight alkyl group having 1 to 6 carbon atoms, carbon
  • a sulfinyl group such as a methylsulfuryl group, an ethylsulfuryl group, a normalpropylsulfuryl group, or an isopropylsulfuryl group.
  • C 1 -C alkylsulfonyl group means a linear alkyl group having 1 to 6 carbon atoms, carbon
  • Amino group substituted with 1 to 6 alkyl groups which may be the same or different, such as dimethylamino group, jetylamino group, methylethylamino group, methylnormalpropylamino group, ethylisopropyl.
  • Amino group dinormal propylamino group, diisopropylamino group, dinormal butylamino group, normal propyl normal butylamino group, methyl normal butylamino group, diisobutylamino group, disecondary butyl amino group, ditertiary butyl An amino group, an ethyl normal pentyl amino group, a di n-pentyl alumino group, an ethyl n-hexyl alumino group, a di n-hexyl alumino group, etc.
  • alkyl group an amino group, an ethyl normal pentyl amino group, a di n-pentyl alumino group, an ethyl n-hexyl alumino group, a di n-hexyl alumino group, etc.
  • a substituted carbocyclic group for example, a methyl carbo yl group, an ethyl carbo ol group, a normal propyl carbo ol group, an isopropyl carbo ol group, a normal butyl carbonyl group, an isobutyl carbo ol group, a secondary butyl carbo ol; Group, tertiary chinorecanol boninole group, nonolemanole pentinorecanoreboninore group, nonolemanolehexinorecanolevonole group and the like.
  • heterocyclic group refers to a 3- to 8-membered heterocyclic group having at least one heteroatom selected from an oxygen atom, a sulfur atom, or nitrogen atom, and includes, for example, an oxsilane ring, oxetane ring, furan ring, dihydro Furan ring, tetrahydrofuran ring, thiophene ring, dihydrothiophene ring, tetrahydrothiophene ring, pyrrole ring, pyrroline ring, pyrrolidine ring, pyran ring, dihydran pyran ring, tetrahydropyran ring, thiane ring, oxazole ring, isoxazole ring, thi A group having an azole ring, isothiazole ring, imidazole ring, triazole ring, pyrazole ring, pyridine ring, pyrimidine ring,
  • C 1 -C and the like indicate a range of carbon numbers such as 1 to 5 and 1 to 6 carbon atoms.
  • scale 1 and R 2 together are oxygen atom, sulfur atom, nitrogen atomic energy 3 to 8 membered ring containing at least one hetero atom selected” means, for example, pyrroline ring, pyrrolidine ring, Examples include a virazoline ring, a virazolidine ring, an oxazoline ring, an oxazolidine ring, an isoxazoline ring, an isoxazolidine ring, a thiazoline ring, a thiazolidine ring, an isothiazoline ring, an isothiazolidine ring, a piperidine ring, a piperazine ring, and a morpholine ring.
  • R 1 is preferably C-C alkyl.
  • halogen atom which may be different, a C-C alkyl group, a halo C-C alkyl group, C
  • a phenyl group having the above substituent more preferably a C-C alkyl group, halo C-C
  • a halo C-C alkoxy group force is a selected phenyl group having one or more substituents.
  • R 2 is preferably a hydrogen atom, a C-C alkyl group, C-C alkoxy C-C alkyl
  • 1 8 2 8 group more preferably a hydrogen atom, a C 1 -C alkyl group or a C 1 -C alkyl carbo-
  • R 3 is preferably a C-C alkyl group, a halo C-C alkyl group, a C-C alkyl group,
  • alkyl group halo C-C alkyl group, C-C alkoxy group or halo C-C alkoxy group
  • substitution position of R 3 is the 4-position of the pyridine ring.
  • R 4 is preferably a C-C alkyl group, a halo C-C alkyl group, a C-C alkoxy C-
  • halo C-C alkyl group More preferably a halo C-C alkyl group, a halo C-C alkoxy C-C alkyl
  • X is preferably an oxygen atom or a single bond
  • Y is preferably an oxygen atom
  • m is preferably 1
  • n is preferably 1 or 2.
  • Examples of the salts of the phenylpyrrolidines represented by the general formula (I) include acetate, propionate, butyrate, oxalate, adipate, dodecanedioate, laurate, stearate, trifluoro Acetate, fumarate, maleate, benzoate, phthalate, etc.
  • Examples thereof include sulfonates such as salts; inorganic acid salts such as hydrochlorides, sulfates, nitrates and carbonates.
  • the pyrrolidines or salts thereof of the present invention represented by the general formula (I) are novel compounds and can be produced, for example, according to the following production method.
  • W is a halogen atom, a trifluoromethylsulfo-oxy group, a methanesulfo-oxy group, p— Indicates a leaving group such as a toluenesulfonyloxy group.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction.
  • alcohols such as methanol, ethanol, and isopropyl alcohol
  • aromatic carbonization such as benzene, toluene, and xylene.
  • Ketones such as ruketone and methyl isobutyl ketone; halogenated hydrocarbons such as chloroform and dichloromethane; water; esters such as methyl acetate and ethyl acetate; ethers such as jetyl ether, tetrahydrofuran and dioxane;
  • Examples include polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and pyridine. These inert solvents can be used alone or in admixture of two or more. I'll do it.
  • Examples of the base that can be used in this reaction include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate. Inorganic salts such as potassium fluoride; organic bases such as pyridine and triethylamine, etc., and the amount used is in the range of equimolar to excess molar relative to the phenylboronic acid represented by the general formula (VII).
  • the reaction can be carried out by appropriately selecting in step 2 and preferably 2 moles are used.
  • Transition metal catalysts that can be used in this reaction include palladium on carbon, palladium acetate, dichlorobis (triphosphine) palladium, tetrakis (triphenylphosphine) paradium. And palladium compounds such as tris (dibenzylacetone) palladium, bis (triphenylphosphine) nickel chloride and tetrakis (triphenylphosphine) nickel-like compounds.
  • the amount used may be appropriately selected from the range of 0.0001 mole to equimolar to the pyridine represented by the general formula (II), and the reaction is preferably performed. It is good to use double mole.
  • phosphine ligands such as triphenylphosphine, tritolylphosphine, tri-t-butylphosphine, etc.
  • the amount used is 0.5 times that of the transition metal catalyst. It is preferable to select appropriately in the range of mol to 100 times mol, preferably in the range of equimolar to 10 times mol. It is also possible to carry out the reaction without using a ligand.
  • the reaction temperature is suitably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of room temperature to 120 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 48 hours.
  • the solvent is distilled off under reduced pressure, water is added, Insoluble in benzene, toluene, xylene, etc .; halogenated hydrocarbons such as chloroform, dichloromethane, etc .; extracted with esters such as ethyl acetate, washed with saturated saline, and then anhydrous sodium sulfate And drying with a drying agent such as anhydrous magnesium sulfate, and the solvent may be distilled off under reduced pressure. If a solvent insoluble in water is used, water is added to the reaction mixture, and the mixture is separated.
  • the organic layer is washed with saturated Japanese saline, dried with a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate, and reduced pressure. And the solvent may be distilled off. If the residue obtained after distilling off the solvent is purified by recrystallization, suspension washing, column chromatography or the like, the compound represented by the general formula (I), which is the target product, can be obtained.
  • a drying agent such as anhydrous sodium sulfate or anhydrous magnesium sulfate
  • a general reaction is achieved by reacting the carboxylic acid represented by the general formula (III) and the amine represented by the general formula (IV) in the presence of a base and a condensing agent in the presence or absence of an inert solvent.
  • a compound represented by the formula (I) can be produced.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not directly participate in this reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, etc .
  • acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone
  • Halogenated hydrocarbons such as chloroform and dichloromethane
  • Water Esters such as methyl acetate and ethyl acetate
  • Ethers such as diethyl ether, tetrahydrofuran and dioxane
  • polar solvents such as dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, and pyridine.
  • Examples of the base that can be used in this reaction include alkali metal hydrides such as sodium hydride; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal carbonates such as sodium carbonate and potassium carbonate. Inorganic salts such as potassium fluoride; organic bases such as pyridine, DBU, triethylamine and the like. The amount used is equimolar to excess molar relative to the amine represented by the general formula (IV). The reaction may be performed by selecting appropriately within the range.
  • Examples of the condensing agent that can be used in this reaction include carbonyldiimidazole, dicyclohexylcarbodiimide, 2-iodine chloride, 1-methylpyridium, and the use amount thereof is represented by the general formula (III).
  • the reaction may be carried out by appropriately selecting in the range of equimolar to excess molar relative to the carboxylic acid.
  • the carboxylic acid represented by the general formula (III) and the amine represented by the general formula (IV) may be used in an equimolar amount.
  • the amine represented by IV) should be used in excess.
  • the reaction temperature is suitably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of room temperature to 120 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 48 hours.
  • the target compound of the general formula (I) can be isolated by the same method as in Production Method 1.
  • Production method 3 Production by reaction of acid halides with amines
  • the acid represented by the general formula (V) is reacted with the amine represented by the general formula (IV) in the presence or absence of an inert solvent and a base.
  • the compounds represented can be produced.
  • the inert solvent and the base that can be used in this reaction are the same as those in Production Method 2, and the amount of the base used is generally equimolar to excess molar relative to the acid or halide represented by the formula (V). You can select the reaction within the range of and perform the reaction.
  • reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of 0 ° C to 80 ° C. Reaction time is constant depending on reaction scale and reaction temperature Not, it ranges from a few minutes to 48 hours.
  • Production method 4 Production by reaction of carbonyl compound and oxiamines
  • the carbonyl compound represented by general formula (la) is reacted with oxyamines or acid addition salts thereof represented by general formula (VI) in the presence or absence of an inert solvent and a base. As a result, a compound represented by the general formula (lb) can be produced.
  • the base that can be used in this reaction is the same as in Production Method 2, and the amount used is generally appropriately selected within the range of equimolar to excess molar with respect to the oxiamines represented by formula (VI). Just do it.
  • the reaction temperature is suitably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of room temperature to 80 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 48 hours.
  • the target compound of the general formula (lb) can be isolated by the same method as in Production Method 1.
  • the inert solvent and base that can be used in this reaction are the same as in Production Method 2, and the amount of the base used is in the range of equimolar to excess molar relative to the compound represented by the general formula (VIII). If you select and respond appropriately.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and is preferably in the range of 0 ° C to 100 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but is in the range of several minutes to 48 hours.
  • the target compound of the general formula (I) can be isolated by the same method as in Production Method 1.
  • the pyrrolidines represented by the general formula (Id) and an oxidant in the presence or absence of an inert solvent By reacting in the presence, the compound represented by the general formula (Ie) can be produced.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it is not directly involved in this reaction.
  • aromatic hydrocarbons such as benzene, toluene, xylene, etc .
  • Ketones such as ethyl ketone and methyl isobutyl ketone
  • Halogenated hydrocarbons such as chloroform and dichloromethane
  • Water Esters such as methyl acetate and ethyl acetate
  • Ethers such as diethyl ether, tetrahydrofuran and dioxane
  • Acetonitrile And polar solvents such as N, N-dimethylformamide, N-methylpyrrolidone and dimethyl sulfoxide.
  • oxidizing agent examples include m-peroxybenzoic acid, hydrogen peroxide, and peracetic acid.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of 0 ° C to 25 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but ranges from a few minutes to 48 hours.
  • the production method 1 may be used.
  • the compound represented by the general formula (II) as an intermediate is, for example, a method described in International Publication No. 00Z175112, European Patent Application Publication No. 0053011 or European Patent Application Publication No. 447004. It can be manufactured according to
  • the compound represented by the general formula (III) as an intermediate can be produced, for example, according to the method described in International Publication No. 04Z014844 pamphlet or International Publication No. 04Z002948 pamphlet.
  • the intermediate compound represented by the general formula (IV) is commercially available and may be used.
  • the compound represented by the general formula (V), which is an intermediate, is obtained from the corresponding compound (III). It can be produced by halogenation by a conventional method using a catalyst.
  • the salts of the phenylpyrrolidines of the present invention can be produced by the following method.
  • R 2 , R 3 , R 4 , X, Y, m, n and p are the same as described above, and A represents an inorganic acid or an organic acid.
  • the salt represented by the general formula (If) is obtained by reacting the phenylpyrrolidine represented by the general formula (I) with an inorganic acid or an organic acid in the presence or absence of an inert solvent. It can be manufactured.
  • an organic acid or an inorganic acid can be used as an acid that can be used in this reaction.
  • an organic acid acetic acid, propionic acid, butyric acid, oxalic acid, adipic acid, dodecanedioic acid, lauric acid, stearic acid, Carboxylic acids such as trifluoroacetic acid, fumaric acid, maleic acid, benzoic acid, phthalic acid; sulfonic acids such as methanesulfonic acid, 1,3 propanedisulfonic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, etc. Can do.
  • inorganic acids include hydrochloric acid, sulfuric acid, nitric acid, and carbonic acid.
  • the inert solvent that can be used in this reaction is the same as in Production Method 6.
  • this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of the phenylpyridines represented by the general formula (I) and the inorganic acid or organic acid, but any of the reactants can be used in excess.
  • the inorganic acid or organic acid is preferably used in excess.
  • the reaction temperature is preferably in the range of 50 ° C to the boiling point of the inert solvent used, and preferably in the range of 0 ° C to 25 ° C.
  • the reaction time is not constant depending on the scale of the reaction and the reaction temperature, but ranges from a few minutes to 48 hours.
  • the solvent is distilled off under reduced pressure, and the crystals are separated by filtration to produce inorganic acid salts and organic acid salts. This is sufficient, but if you want to further purify, wash with the above inert solvent. By doing so, high-purity phenyluridine acid addition salts can be produced.
  • Dissolving, separating, suspending, mixing, impregnating, adsorbing or adhering to appropriate dosage forms such as suspensions, milk suspensions, emulsions, solutions, wettable powders, granules, powders, tablets, jumbo drugs,
  • appropriate dosage forms such as suspensions, milk suspensions, emulsions, solutions, wettable powders, granules, powders, tablets, jumbo drugs.
  • the preparation may be used as a knocking agent.
  • Examples of the inert carrier that can be used in the present invention can be either solid or liquid.
  • Examples of the material that can be a solid carrier include vegetable powders (for example, soybean powder, cereal flour, wood flour, husk) Powder, sawdust, tobacco stem powder, walnut shell powder, bran, fiber powder, residues after extraction of plant extracts), synthetic polymers such as pulverized synthetic resin, clays (e.g.
  • silica eg diatomaceous earth, silica sand, mica, white carbon (hydrous finely divided silicon, hydrous silicic acid, synthetic high-dispersion silicic acid that contains calcium silicate as the main component) ;
  • Activated carbon natural minerals (such as yow powder, pumice, calcined diatomaceous earth, attapulgite and zeolite), brick ground, fly ash, sand, plastic Examples include mineral carriers such as polyethylene, polypropylene, and polysalt vinylidene, inorganic mineral powders such as calcium carbonate and calcium phosphate, chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride, compost, etc.
  • the material that can be used as a liquid carrier is selected from those having solvent ability itself and those capable of dispersing the active ingredient compound with the aid of an auxiliary agent without having solvent ability.
  • the following carriers can be exemplified as representative examples, and these are used alone or in the form of a mixture of two or more, such as water, alcohols (for example, methanol, ethanol, isopropanol, butanol, ethylene).
  • ketones eg, acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, etc.
  • ethers eg, ethyl ether, dioxane, cellosolve, dipropyl ether, tetrahydrofuran, etc.
  • aliphatic carbonization Hydrogens e.g. kerosene, mineral oil, etc.
  • aromatic hydrocarbons e.g.
  • esters eg, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.
  • amides eg, dimethylformamide, ethylformamide, dimethylacetamide) Etc.
  • nitriles eg, acetonitrile
  • adjuvants typical adjuvants exemplified below can be mentioned, and these adjuvants are used depending on the purpose and are used alone, in some cases, in combination with two or more kinds of adjuvants, In some cases it is also possible to use no adjuvants.
  • Surfactants are used for emulsification, dispersion, solubilization and Z or wetting purposes of the active ingredient compounds, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher fatty acid esters, polyoxy Interfaces such as ethylene succinate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkylaryl sulfonate, naphthalene sulfonic acid condensate, lignosulfonate, and higher alcohol sulfate An activator can be exemplified.
  • auxiliaries such as casein, gelatin, starch, methylcellulose, carboxymethylcellulose, Adjuvants such as xanthan gum, gum arabic, polyvinyl alcohol, pine oil, coconut oil, bentonite, and lignite sulfonate can also be used.
  • adjuvants such as wax, stearate, alkyl phosphate and the like may be used.
  • auxiliary agents such as naphthalene sulfonic acid condensate and condensed phosphate can be used.
  • an antifoaming agent for example, an auxiliary agent such as silicone oil can be used.
  • the compounding ratio of the active ingredient compound can be adjusted as necessary and is not particularly limited.
  • the compounding ratio is about 0.001 to 90% by weight.
  • the compounding ratio of the active ingredient compound is preferably about 0.01 to 50% by weight, more preferably about 0.1 to 10% by weight.
  • the compounding ratio of the active ingredient compound is preferably about 0.01 to 90% by weight, more preferably about 0.1 to 60% by weight. is there.
  • a preparation containing a pyrrolidine or a salt thereof represented by the general formula (I) of the present invention is diluted with water and applied, the adhesiveness and spreadability are improved, and the herbicidal effect is improved.
  • an auxiliary agent such as a spreading agent may be added to the spray liquid.
  • Adjuvants such as spreading agents used include surfactants (the above-mentioned nonionic surfactants, cationic surfactants, anionic surfactants, amphoteric surfactants), paraffin, Examples include butyl acetate, polyacrylate, ethylene glycol, propylene glycol, polyethylene glycol, polypropylene glycol, crop oil (mineral oil, animal and vegetable oils), and liquid fertilizer.
  • adjuncts such as spreading agents
  • the amount of adjuncts such as spreading agents varies depending on the type. Usually, it is appropriate to add 0.01 to 5% by weight to the spray liquid. Depending on the type of the adjuvant, it is possible to add it as a component in the preparation in advance.
  • the application rate of the herbicide containing as an active ingredient the fur-rubiridines or salts thereof represented by the general formula (I) of the present invention is the structure of the compound, the target weed, the treatment time, the treatment method, the properties of the soil, etc.
  • the force varies depending on the conditions.
  • the amount of active ingredient per hectare is 2 to 2000 g, preferably 5 to LOOOg.
  • the target weeds of the herbicide of the present invention include, for example, Shiroza, Akaza, Inutade, Harutade, Inubu, Aaubu, Jacobe, Hotokenoza, Ichibi, Onamomi, Maruasaagao, Datura, Seiokarasana, Yaemdara Broadleaf weeds such as Seythmus mille, Oro shagiku, Kosendandasa, Meishiba, Ohishiba, Inubie, Enokorogusa, etc. Narrow-leaved weeds.
  • broad-leaved weeds such as Kakashidasa, Azena, Konogi, Abnomé, Mizono-kobe, Heramodaka, Omodaka and Urica-koji
  • narrow-leaved weeds such as Tainubie, Tamagayari, Inuhotarui and Mizugayari.
  • the herbicide of the present invention can control the above weeds in upland fields and paddy fields by any treatment method of soil treatment, foliage treatment or flooding treatment.
  • crops to which the herbicide of the present invention is applied include corn, wheat, barley, rice, soybean, and the like, and these crops have little effect in both soil treatment and foliage treatment. It can be used as a selective herbicide in crop cultivation.
  • the herbicide of the present invention for example, in the soil treatment and foliage treatment for crops that have been improved in genetic traits such as corn, wheat, barley, rice, soybean, etc. and imparted drug resistance etc. However, it can be used as a selective herbicide in the cultivation of these crops.
  • the herbicide of the present invention can be mixed and applied with other pesticides such as insecticides, fungicides, plant growth regulators, and fertilizers used in the same field. In addition, in order to further stabilize the herbicidal effect, it can be mixed with other herbicides.
  • both preparations may be mixed at the time of application, but they may be applied in advance as preparations containing both.
  • herbicides that can be suitably mixed and applied for the above purpose include the following.
  • Glyphosate and its salts Darifosinate and its salts, Bialafos and its salts, Organic phosphorus herbicides such as butamifos, arlofos, benzulide, sulfarate, diarates, triarates, EPTC, butyrate, esprocalp, thiobencalp (benchocarb), molly Carbamate herbicides such as Nate, Isopolynate, Dimepiperate, Pyributicalp, FenMedifam, Chlorprofam, Ashram, etc.
  • Organic phosphorus herbicides such as butamifos, arlofos, benzulide, sulfarate, diarates, triarates, EPTC, butyrate, esprocalp, thiobencalp (benchocarb), molly Carbamate herbicides such as Nate, Isopolynate, Dimepiperate, Pyribut
  • Urea herbicides metazachlor, araclos monore, butacronore, pretila clonore, acetoclonole, metolacronore, tenino Amide herbicides such as recral, diethyl, dimethenamide, propanil, diflufen-can, mefenacet, flue naset, bromobutide, isoxaben (benzamizole), triflura Di-tro-phosphorus herbicides such as phosphorus, benfluralin, prodamine, oryzalin, butralin, pendimethalin,
  • Diphenyl ether herbicides such as chloro-trophene, chloromethoxyl, oxyfluorfen, biphenox, acifluolfen and salts thereof, fluoroglycophene, lactofen, fomesafen, acrophene, and amides Sulfuron, Chlorimlonethyl, Sulfomethylon methinole, Primisnorephron, Benzenoreflon methinore, Ethoxysulfuron, Cyclosnole Famron, Chlorsulfuron, Metosulfuronmethyl, Tribenuron methyl, Triasulfuron, Sinosulfuron, Etamethsulfuron Methyl, triflusulfuron methyl, prosulfuron, thifensulfuron methyl, pyrazosulfuronethyl, halosulfuron methyl, frazasulfuron, rimsulfuron, nico
  • herbicides include indanofan, funoleridone, funole mouth chloridone, flurtamone, norefnorrazon, caffen stranol, fentrazamide, snolefentrazone , Force norefentra zonethyl, pentoxazone, oxadiazone, oxadialgyl, pyraflufenethyl, isopropazole, flupoxam, cromazone, isoxaflutol, isoxachlortol, dithiopyr, thiazopyr, pirithiovac and its salts, pyriminoback methyl, bispiri Bags and salts thereof, bromacil, terbacil, lenacyl, fluprobasil, oxadichrome mehon, symmetrine, chlorphthalim, full microlac pentyl, full Oxazine, cinidoneethyl, azafenidin
  • 6-n- (4-fluorophenol) -4-methylpyridine-2-force Ruboxamide (0.30 g, 1.13 mmol)
  • 3 rifluoromethoxyphenyl-poronic acid (0.28 g, 1. 36 mmol)
  • 2M aqueous sodium carbonate solution 1.5 ml, 3.0 mmol
  • toluene (3.0 ml)
  • tetrakistriphenylphosphine palladium (0.10 g 0.087 mmol
  • the above is uniformly mixed and pulverized to obtain a powder.
  • the above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to obtain granules.
  • the above is uniformly mixed and ground to obtain a wettable powder.
  • Test Example 1 Herbicidal effect test on paddy weeds before emergence
  • Test Example 2 Herbicidal effect test on paddy field weeds after emergence.
  • a 75 cm 2 plastic pot is filled with soil (Pyongyang soil), seeds of Inubie and Yinhotarui, which are paddy field weeds, are sown and covered with 75 cm 3 of soil mixed with Azena and Mizojakobe seeds, then 5 cm deep It was flooded and raised in a greenhouse.
  • soil Pulongyang soil
  • seeds of Inubie and Yinhotarui which are paddy field weeds
  • 75 cm 3 of soil mixed with Azena and Mizojakobe seeds then 5 cm deep It was flooded and raised in a greenhouse.
  • the drug containing the compound of the present invention as an active ingredient was treated as a chemical solution having a predetermined effective dose (gZha).
  • gZha predetermined effective dose
  • security with respect to an important crop, and the useful compound used for it can be obtained.

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Abstract

Dérivé de phénylpyridine représenté par la formule générale (I) dans laquelle R1 représente un alkyle en C1-8, etc. et R2 représente un hydrogène, etc., à condition que R1 et R2 en association l'un avec l'autre puissent former un cycle à 3 à 8 éléments contenant au moins un hétéroatome sélectionné parmi un oxygène, un soufre et un azote ; R3 représente un halogéno, etc. ; R4représente un halo(alkyle en C1-8), etc., à condition que deux R4 adjacents puissent être reliés l'un à l'autre pour représenter un alkylènedioxy en C1-4 ou un halo(alkylènedioxy en C1-4) ; X représente un oxygène, un soufre, -NH- ou une simple liaison ; Y représente un oxygène ou un soufre, m est un nombre entier valant 0-3 ; n est un nombre entier valant 1-5 ; et p est 0 ou 1.
PCT/JP2005/012781 2004-07-12 2005-07-11 Dérivé de phénylpyridine ou sel de celui-ci, herbicide contenant celui-ci comme ingrédient actif et procédé d'utilisation de celui-ci WO2006006569A1 (fr)

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