WO2001000562A1 - Derives d'acide acrylique, leur utilisation et intermediaires pour leur preparation - Google Patents

Derives d'acide acrylique, leur utilisation et intermediaires pour leur preparation Download PDF

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WO2001000562A1
WO2001000562A1 PCT/JP2000/004080 JP0004080W WO0100562A1 WO 2001000562 A1 WO2001000562 A1 WO 2001000562A1 JP 0004080 W JP0004080 W JP 0004080W WO 0100562 A1 WO0100562 A1 WO 0100562A1
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group
optionally substituted
formula
methyl
compound
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PCT/JP2000/004080
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English (en)
Japanese (ja)
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Hiroshi Sakaguchi
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Sumitomo Chemical Company, Limited
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Priority to AU54287/00A priority Critical patent/AU5428700A/en
Publication of WO2001000562A1 publication Critical patent/WO2001000562A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te

Definitions

  • the present invention relates to an acrylic acid derivative and its use.
  • An object of the present invention is to provide a compound having an excellent plant disease controlling effect.
  • Means for Solving the Problems As a result of intensive studies, the present inventors have found that an acrylic acid derivative represented by the following formula (1) has an excellent plant disease controlling effect, and have accomplished the present invention.
  • X represents a CR 4 group or a nitrogen atom
  • Y represents CR 5 or a nitrogen atom
  • RR 2 and R 3 are the same or different
  • a phenoxy group which may be substituted An optionally substituted C1-C9 heteroaryloxy group, an optionally substituted C2-C6 alkoxycarbonyl group,
  • R 4 , R 5 , R 6 R 7 and R 8 are the same or different and are a hydrogen atom, a halogen atom,
  • the present invention provides an acrylic acid derivative represented by the formula (hereinafter, referred to as the present compound), a plant disease controlling agent containing the same as an active ingredient, and a plant disease controlling method using the active ingredient.
  • the present invention provides a compound of formula [XX '] useful as an intermediate for producing the compound of the present invention:
  • a 1 is B (OH) 2 group
  • B (OR 9) represents 2 group or R lfl 3 Sn group
  • R 9 , R 1 . Is a force representing a C 1 -C 10 alkyl group, with two R 9 —CH.
  • CH represents one group or one C (CH 3 ) 2 C (CH 3 ) 2 .
  • ⁇ Is provided. Further, the present invention provides a compound of the formula [ ⁇ ]:
  • L 1 is a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, etc. Represents a leaving group.
  • L 1 is a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, etc. Represents a leaving group.
  • ⁇ In the presence of a base, or a compound of the formula [1] and a compound of the formula
  • L 2 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group
  • W, RR 7 and R 8 has the same meaning as described above.
  • a 2 represents B (OH) 2 group, B (OR 9) 2 group or S n R 1Q 3 group,
  • R 9 and R 1 Represents an alkyl group of C1 ⁇ C 10, one of two R 9 CH 2 CH 2 - group or a C (CH 3) 2 C ( CH 3) may represent a 2 _ group.
  • a method for producing an atalylic acid derivative of the above formula (1) characterized by reacting a compound of formula (1) with a compound of formula [XX ']:
  • halogen atom represented by R and R 3 examples include a chlorine atom, a bromine atom, a fluorine atom and an iodine atom.
  • Examples of the C 1 C 10 alkyl group in the optionally substituted C 1 C 10 alkyl group represented by R ⁇ R 2 and R 3 include, for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl Group, 1-methylpropyl group, pentyl group, 1-methylbutyl group, 1-ethylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 12-dimethylpropyl group, 1, 1 —Dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethylpentyl group, 33-dimethylbutyl group, heptyl group, 37-dimethyloctyl group, nonyl group, decyl group and the like.
  • Examples of the C 2 C 10 alkenyl group in the optionally substituted C 2 C 10 alkenyl group represented by R ⁇ R 2 and R 3 include, for example, a vinyl group, an aryl group, Examples thereof include a methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 2-butul group, a 2-pentyl group, and a 3-methyl-2-butul group.
  • the C 3 to C 1 0 cycloalkyl group in the optionally substituted C 3 to C 1 be the 0 cycloalkyl Le group represented by R ⁇ R 2 and R 3, for example, cyclopropyl group, consequent opening pentyl group, consequent opening Hexyl group and the like.
  • the C 5 ⁇ C 1 0 cycloalkenyl group in the substituted C 5 ⁇ C 1 optionally 0 Shikuroaruke alkenyl group represented by RR 2 and R 3, e.g. cyclopent group, hexenyl group, etc. cyclohexylene.
  • the C 6 -C 10 aryl group in the optionally substituted C 6 -C 10 aryl group represented by R ⁇ R 2 and R 3 includes a phenyl group, an ⁇ -naphthyl group, a ⁇ - And a naphthyl group.
  • Examples of the C 1 -C 9 heteroaryl group in the optionally substituted C 1 -C 9 heteroaryl group represented by RR 2 and R 3 include, for example, a 2 pyridyl group, a 3 pyridyl group, a 4 pyridyl group, and a 2-pyridyl group.
  • Pyrimidinyl group 4-pyrimidinyl group, 2-thenyl group, 3-thenyl group, 2-furyl group, 3-furyl group, pyrrole-1-yl group, 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group , 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 2-oxazolyl group, 5-oxazolyl group, 2-imidazolyl group, 3- (1,2,4-triazolyl) group, 2-benzobenzoyl A 3-benzobenzoyl group, a benzothiazole-2-yl group, a 2-quinolinyl group and the like.
  • the definitive good C 1 through C 6 alkoxy group optionally substituted C 1 through C 6 alkoxy group represented by R ⁇ R 2 and R 3, for example, main butoxy group, an ethoxy group, t _ butoxy group, Penchiruokishi group And a hexyloxy group.
  • the C 1 through C 9 heteroaryl ⁇ reel O alkoxy group in the substituted C 1 through C 9 optionally Heteroariru Okishi group represented by R ⁇ R 2 and R 3, 2- Pirijiruo alkoxy group, 2- (5- Trifluoromethyl) pyridyloxy group, 3-pyridyloxy And a 4-pyridyloxy group, a 2-pyrimidyloxy group, a 4-pyrimidyloxy group, a 5-pyrimidyloxy group, and a 3-cheeroxy group.
  • the C 1 through C 6 alkylthio group in R ⁇ R 2 and R 3 optionally substituted C 1 through C 6 alkylthio group represented by, for example, methylthio group, Echiruchio group, propylthio group, butylthio group, pentylthio group, Hexylthio group and the like.
  • Examples of the C 3 -C 30 trialkylsilyl group in the optionally substituted C 3 -C 30 trialkylsilyl group represented by RR 2 and R 3 include, for example, a trimethylensilyl group, a triethylsilyl group, and a t-butyldimethyl group. Examples thereof include a silyl group, tripentinolesilyl group, trihexylsilyl group, triheptylsilyl group, trioctylsilyl group, trinoersilyl group, and tridecylsilyl group.
  • optionally substituted C 1 through C 1 0 aralkyl kill group an optionally substituted C 2 to C 1 0 alkenyl group
  • it may also be substituted Rere C 2-C10 alkynyl group, optionally substituted C3-C10 cycloalkyl group, optionally substituted C5-C10 cycloalkenyl group, optionally substituted C6-C 10 aryl group, optionally substituted C1-C9 heteroaryl group, optionally substituted C1-C6 alkoxy group, optionally substituted phenoxy group, optionally substituted C1-C9 heteroaryloxy group, C2-C6 alkoxycarbonyl group, optionally substituted C1-C6 alkylthio group and optionally substituted C3-C30 trialkylsilyl
  • the group include a halogen atom (a chlorine atom, a bromine atom, a fluorine atom, an iodine atom ,
  • C1-C10 alkyl group [for example, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, 1-methylpropyl group, pentyl group, 1-methylbutyl group, 1-methylbutyl group, 2 —Methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1,1-dimethyl Propyl, hexyl, 1-methylpentyl, 1-ethylpentyl, 3,3-dimethylbutyl, heptyl, 3,7-dimethyloctyl, etc., nonyl, decyl),
  • C3-C20 trialkylsilyl group e.g., trimethylsilinole group,
  • a C1-C10 haloalkyl group for example, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafuronoethyl group, etc.
  • C3-C10 cycloalkyl group e.g., cyclopropyl group, pen-pentyl group, hexa-hexyl group, etc.
  • a C 1 -C 10 alkoxy group for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, an isobutoxy group, an n_pentyloxy group, etc.
  • C1-C10 haloalkoxy group for example, trifluoromethoxy group, difluoromethoxy group, bromodifluoromethoxy group, chlorodifluoromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group , 1, 1, 2, 2-tetrafluoroethoxy group etc.
  • C 1 -C 10 alkylthio group for example, methylthio group, ethylthio group, n_propylthio group, n-butylthio group, isobutylthio group, sec-butylthio group, n-pentylthio group, n-hexylthio group, etc.
  • C1-C10 haloalkylthio group for example, trifluoromethylthio group, difluoromethylthio group, bromodifluoromethylthio group, chlorodifluoromethylthio group, fluoromethylthio group, 2,2,2-trifluoro Oloethylthio group, 1, 1, 2, 2-tetrafluoroethylthio group, etc.
  • C2-C10 alkoxy carbonyl group [methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, n —Pentyloxycarbonyl group, n-hexyloxycarbonyl group, etc.), phenyl group, pyridyl group, pyrimidyl group, phenoxy group, benzyloxy group, pyridine-1T oxy group ⁇ where the phenyl group, pyridyl group, Pyrimidyl Group, a phenoxy group, a benzyloxy group and a pyridine-1-yloxy group each represent a halogen atom (eg, a chlorine atom), a C 1 -C 6 alkyl group (eg, a methyl group, an ethyl group, etc.),
  • Examples include those which may be substituted with at least one same or different substituent selected from the group including amino acids, hydroxyl groups, cyano groups, nitro groups and the like.
  • Examples of the halogen atom represented by R 4 , R 5 , R 6 , R 7 and R 8 include a chlorine atom, a bromine atom, a fluorine atom and an iodine atom.
  • R ⁇ R 5, RR 7 and R 8 methyl group
  • Echiru group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a 1-methylpropyl group can give.
  • R 4 as the C 1 through C 4 haloalkyl group represented by R 6, R 7 and R 8, eg if Furuoromechiru groups, trifluoperazine Ruo Lome Chino les group, trichloromethyl group, Kuronoreji Furuoromechiru, black hole propyl And a chlorobutyl group.
  • the terms (E) and (Z) as used herein are defined by the Kahn-Ingold-Prelog rule, which is widely used to refer to geometric isomers.) Is the following formula ():
  • examples of more preferred compounds in terms of the efficacy of controlling plant diseases include methyl 3-methoxy-2- (2-methyl-15-fueurphenoxy) -12-propanoate (described below).
  • the compound of the present invention can be produced, for example, according to the following [Production method A], [Production method B] or [Production method C]. Depending on the content of X or Y, for example, it can be manufactured according to [Manufacturing method D].
  • these production methods and the like will be described with reference to Schemes 1 to 11, but the compounds of the present invention and the compounds shown in the schemes will be described below.
  • the preferred embodiment is exemplified using the (Z) -form.
  • the compounds of the formulas [XX'L [1 '] and [ ⁇ '] are exemplified in the following scheme.
  • the reaction shown in the scheme can be carried out without any problem using any of the isomers ⁇ and ⁇ .
  • the reaction can be similarly carried out using a mixture of both isomers. In these production methods, a protecting group can be used if necessary.
  • L 1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a p-toluenesulfonyloxy group, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group
  • L 3 represents a tutorials Kirushiriru group such as trimethylsilyl group
  • WXYR 1, R 2 RR 6 R 7 and R 8 represent the a same meaning.
  • the reaction temperature is generally Ri range der of 0 1 0 0 ° C, the formula CH 3 - amount of the compound represented by L 1, the compound 1 mode represented by the formula [I] It is usually in the range of 110 moles per mole.
  • the amount of the base used in the reaction is usually in the range of 1 to 10 mol per 1 mol of the compound represented by the formula [I].
  • the base include inorganic bases such as sodium hydroxide, sodium hydroxide, sodium carbonate, sodium carbonate, calcium carbonate, sodium hydride, and alkalis such as potassium methoxide, sodium methoxide, sodium methoxide.
  • inorganic bases such as sodium hydroxide, sodium hydroxide, sodium carbonate, sodium carbonate, calcium carbonate, sodium hydride, and alkalis such as potassium methoxide, sodium methoxide, sodium methoxide.
  • metal alkoxides organic bases such as pyridine, triethylamine, ethyldiisopropylamine, and aniline, and mixtures thereof.
  • Solvents include, for example, 1,4-dioxane, tetrahydrofuran, ethyleneglycol-no-resin-methino-leno-tenol, t-butynoleme Chirue - an ether solvent such as ether, n - hexane, n - aliphatic hydrocarbons solvents such as heptane, aromatic hydrocarbon solvents such as toluene, halogenated hydrocarbon solvents monochrome port benzene, pyridine, Toryechiruamin, N Organic base solvents such as N, N-dimethylaniline, etc., ester solvents such as butyl acetate and ethyl acetate, nitrile solvents such as acetonitrile, N, N-dimethylformamide, dimethyl sulfoxide, water, etc. or a mixture thereof Is raised.
  • solvents include, for example, 1,4-dioxan
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • step a ′ of scheme 1 the compound represented by the formula [I] and the compound represented by the formula N 2 CH—L 3 are usually reacted at a temperature in the range of 120 to 50 ° C.
  • the amount of the compound represented by the formula N 2 CH—L : s is usually in the range of 1 to 10 mol per 1 mol of the compound represented by the formula [I].
  • the reaction is usually carried out in a solvent, and for example, the same solvent as exemplified in the above step a can be used.
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • a 2 , L 2 , W, X, Y, RR 2 , R 3 , RR 7 and R 8 represent the same meaning as described above.
  • the reaction of Scheme 2 is usually performed in the range of 20 to 120 ° C.
  • the amount of the compound represented by the formula [III] to be used is generally in the range of 1 to 5 mol per 1 mol of the compound represented by the formula [II].
  • the amount of the catalyst used in the reaction is usually in the range of 0.001 to 0.1 mol per 1 mol of the compound represented by the formula [II].
  • the catalyst include palladium acetate (11), tetrakis (triphenylphosphine) palladium (0), ⁇ 1,1'-bis (diphenylphosphine) phenoctene) dichloropalladium (II) methylene chloride Complex, bis- (triphenylphosphine) palladium
  • the reaction may be carried out, if necessary, with a base (eg, an inorganic base such as sodium acetate, potassium acetate, potassium carbonate, tripotassium phosphate, sodium bicarbonate) or a phase transfer catalyst (eg, tetrabutylammonium bromide, benzyltriethyl) It may be performed in the presence of a quaternary ammonium salt such as ammonium bromide.
  • a 2 is S nR 10 3 group (wherein R 1G is, the R 9 and. Representing the same C1 ⁇ C10 alkyl group) in the compound represented by the formula [III] when it is, the necessary In some cases, it is carried out in the presence of copper oxide (11) and silver oxide (II).
  • the reaction is usually performed in a solvent.
  • the solvent include alcohol solvents such as methanol, ethanol, propanol, butanol, and isopropanol;
  • Ether solvents such as 4-dioxane, tetrahydrofuran, ethylene glycolone resin methinolate ether, t-butyl methyl ether; aliphatic hydrocarbon solvents such as n-hexane and n-heptane; aromatic hydrocarbon solvents such as toluene; Examples include nitrile solvents such as acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, water and the like, or mixtures thereof.
  • the reaction is more specifically carried out, for example, by the method described in J. Org, Chem., 1999, 62, 7170-7173, J. Org. Chem., 1995, 60, 7508—75 10 or according to the method described in Ange w. Chem. Int. Ed. Engl., 1986, 25, 508—524. Do it.
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent, concentration, and the like, to obtain a target compound. If necessary, the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • the compound wherein W is an oxygen atom can also be produced, for example, according to the method shown in the following scheme 3 or scheme 4.
  • Step 31 of Scheme 3 is the same as described in Step a of Scheme 1 except that Formula [I] is
  • the reaction in Step 3j of Scheme 3 is usually performed in the range of 0 to 80 ° C.
  • the amount of HCOOCH 3 to be used in the reaction is usually in a range of 1-100 moles per mole of the compound of the formula [XV].
  • the reaction is usually carried out in the presence of a base.
  • a base examples include inorganic bases such as sodium hydride and potassium hydride, alkali metal alkoxides such as sodium methoxide, sodium ethoxide, and potassium teroxide, and sodium amide.
  • alkali metal amides such as lithium amide, lithium diisopropyl amide, sodium hexamethyldisilazide and lithium hexamethyldisilazide, and mixtures thereof.
  • the reaction is carried out in a solvent, if necessary.
  • the solvent include ether solvents such as 1,4-dioxane, tetrahydrofuran, ethyleneglycol-1-dimethinoleate, and t-butylmethyl ether; Aliphatic hydrocarbon solvents such as xane and n-heptane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as monochrome benzene; organic bases such as pyridine, triethylamine, N, N-dimethylaniline Solvents, nitrile solvents such as acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, N, N-dimethinole-2-imidazolidone, sulfolane and the like, and mixtures thereof.
  • ether solvents such as 1,4-dioxane, tetrahydrofuran, ethyleneglycol-1-dimethin
  • reaction solution is treated with an acidic aqueous solution such as dilute hydrochloric acid, and then subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound. If necessary, the desired compound can be isolated by purification by recrystallization, chromatography or the like.
  • the reaction of Steps 3f and 3g in Scheme 3 is usually performed in the range of 0 to 80 ° C, and the amount of the compound represented by the formula I ⁇ CH 2 COOCH 3 is determined by the formula [XII] or the formula [X]. It is usually in the range of 1 to 5 mol per 1 mol of the compound shown.
  • the reaction is usually performed in the presence of a base, and the amount of the base to be used is generally in the range of 1 to 10 mol per 1 mol of the compound represented by the formula L CHsCOOCHs.
  • a base for example, sodium hydroxide, hydroxylated room, carbonic acid room, hydrogenated sodium, Inorganic bases such as potassium hydride; alkali metal alkoxides such as potassium-t-butoxide, sodium methoxide and sodium ethoxide; organic bases such as pyridine, triethylamine, ethyldiisopropylamine, N, N-dimethylaniline; Alternatively, a mixture thereof may be mentioned.
  • the reaction is carried out in a solvent as necessary, and examples of the solvent include the solvents exemplified in Step a of Scheme 1.
  • the target compound can be obtained by performing the same treatment as described in step a.
  • Steps 3b, 3d, and 3h are performed by a reduction reaction of a nitro group.
  • a substituent is appropriately introduced by, for example, a halogenation method, and in steps 3c, 3e, and 3i, It may be performed by a Sandmeyer reaction or the like.
  • step 4f of scheme 4 can be carried out under the same conditions as the reaction of step 3j of scheme 3, and the base to be used and the solvent to be used if necessary are described in step 3j. And the same as those exemplified in the above.
  • the amount of HCOOCH 3 to be used in the reaction is in the range of usually 1-100 moles per mole of the compound represented by the formula [IX].
  • reaction mixture is treated in the same manner as described in step 3j to isolate the target compound can do.
  • the compound [ ⁇ ] in the description of the step in Scheme 2 is a compound represented by the formula [VI], a compound represented by the formula [XII] or a compound represented by the formula [XII] [XV].
  • step 5e of scheme 5 is performed under the same conditions except that the compound of formula [XXX] is used instead of the compound of formula [I] in steps a and a 'of scheme 1. Can be implemented.
  • Step 5c of Scheme 5 is carried out under the same conditions as in Step 3j of Scheme 3 except that the compound of Formula [XXIX] is used instead of the compound of Formula [XV], and the target compound is obtained. Obtainable.
  • Step 5d in Scheme 5 can be carried out under the same conditions as in Step 3k of Scheme 3 except that a compound represented by the formula [XXX] is used, and the desired product can be obtained.
  • the reaction of Step 5a in Scheme 5 is usually performed in the range of 20 to 120 ° C.
  • the amount of dimethyl malonate to be used is generally in the range of 1 to 3 moles per mole of the compound represented by the formula [XXVII].
  • the reaction is usually carried out in the presence of a base, and the amount of the base to be used is generally in the range of 1 to 10 mol per 1 mol of the compound represented by the formula [XXVII].
  • the base include inorganic bases such as sodium hydroxide, potassium hydroxide, potassium carbonate, sodium hydride, potassium hydride, and alkali metal alkoxides such as potassium t-butoxide, sodium methoxide, and sodium ethoxide.
  • organic bases such as pyridine, triethylamine, ethyldiisopropylamine, N, N-dimethylaniline, and mixtures thereof.
  • the reaction is carried out in a solvent as necessary.
  • the solvent include 1,4-dioxane, tetrahydrofuran, ether solvents such as ethylene glycol dimethyl ether and t-butyl methyl ether, n- hexane, n-heptane and the like.
  • Alcohol solvents, nitrile solvents such as acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, water and the like, and mixtures thereof.
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • the compound represented by the formula [XXVII] can be produced, for example, according to the production method described in JP-A-11-219579.
  • the reaction of step 5b of Scheme 5 is usually performed in the range of 80 to 250 ° C.
  • the reaction may be carried out in the presence of an inorganic salt such as lithium chloride and lithium bromide, if necessary.
  • the reaction is carried out in a solvent, if necessary.
  • the solvent include ether solvents such as 1,4-dioxane, triglyme, and tetraglyme; aliphatic hydrocarbon solvents such as n-octane; and toluene and xylene.
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • the compound represented by the formula (III) can be produced, for example, by the method shown in the following scheme 6.
  • the reaction of scheme 6 can be carried out, for example, by reacting a compound represented by the formula [XVII] with a metal (eg, magnesium, lithium, etc.) in a solvent (eg, diethyl ether, tetrahydrofuran, etc.).
  • a metal eg, magnesium, lithium, etc.
  • a solvent eg, diethyl ether, tetrahydrofuran, etc.
  • the reaction can also be performed by reacting a metal compound with a borate ester (eg, trimethyl borate, triethyl borate, etc.). (More specifically, it is carried out according to the method described in, for example, J. Am. Chem.
  • the solvent catalyst e.g., tetrakis (bird whistle two Rufosufin) palladium (0) etc.
  • the solvent catalyst at (toluene) in the presence in the formula [XV II] are of compounds of represented by the and R ie 3 S n S nR It may be performed by a method of reacting with 1Q 3 (for example, Bu 3 Sn SnBu 3 etc.). (More specifically, for example, it is carried out according to the method described in Chem. Letters, 1981, 829-830.)
  • the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound.
  • the target compound can be isolated by purification by recrystallization, distillation, chromatography or the like.
  • a 1 represents B (OH) 2 group, B (OR 9) 2 group or S nR 1 () 3 group, LW, X, Y, RR 2, R 3, R 6, R 7, R 8, R 9 and R 1. Has the same meaning as described above.
  • the compound represented by the formula [XX] can be produced, for example, by the method shown in the following scheme 9.
  • reaction of Scheme 9 is usually performed in the range of 20 to 100 ° C.
  • a 1 - amount of A 1 is usually in the range of 1 to 5 moles relative to the compound [XXII] 1 mol.
  • the reaction is carried out, for example, in a solvent (dimethyl sulfoxide, N, N-dimethylformamide, etc.) in a base (eg, an inorganic base such as potassium acetate, etc.) and a catalyst (eg, ⁇ 1,1′-bis (diphene) / Refosufuino) fuekisen ⁇ dichloropalladium (II) methylene chloride complex) in the presence of a compound of formula [XXII] and bis
  • reaction solution After completion of the reaction, the reaction solution is subjected to ordinary post-treatments such as extraction with an organic solvent and concentration to obtain a target compound. If necessary, recrystallization, distillation, chromatography, etc. Purification allows isolation of the target compound.
  • a compound in which X and Y in the formula (1) are nitrogen atoms is, for example, a condensation reaction of the compound [XXIII] with a 1,3-dioxo compound in the following scheme 10. May be produced by the production method D.
  • the compound wherein W is an oxygen atom may be produced, for example, according to the method shown by the following scheme 11.
  • the reaction in each step of Scheme 11 can be carried out according to the method of the corresponding step described in Schemes 1 to 10.
  • the compound of the present invention When used as an active ingredient in an agricultural and horticultural fungicide, it may be used as it is without adding any other components, but it is usually a solid carrier, a liquid carrier, a surfactant, and other pharmaceutical auxiliaries. And used in emulsions, wettable powders, wettable powders for granules, emulsions, flowable preparations, powders, granules and the like. These preparations usually contain 0.1 to 90% by weight of the compound of the present invention as an active ingredient.
  • Examples of the solid carrier used in the case of vigorous formulation include minerals such as kaolin clay, atta-palgia clay, bentonite, montmorillonite, acid clay, pyrophyllite, tanolek, diatomaceous earth, calcite, corn cob powder, Fine powders or granules composed of natural organic substances such as walnut shell powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such as synthetic hydrous silicon oxide are examples of the liquid carrier.
  • minerals such as kaolin clay, atta-palgia clay, bentonite, montmorillonite, acid clay, pyrophyllite, tanolek, diatomaceous earth, calcite, corn cob powder, Fine powders or granules composed of natural organic substances such as walnut shell powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such
  • aromatic hydrocarbons such as xylene, alkylbenzene, and methyl naphthalene
  • alcohols such as isopropanol, ethylene glycol, propylene glycol, and cellosolve, acetone, and cyclohexano
  • ketones such as isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum aliphatic hydrocarbons, esters, dimethyl sulfoxide, acetonitrile, water and the like.
  • the surfactant examples include an alkyl ester sulfate, an alkyl (aryl) sulfonate, a dialkyl sulfosuccinate, a polyoxyethylene alkyl aryl-phosphate ester salt, a lignin sulfonate, and a formalin condensate of naphthalene sulfonic acid.
  • nonionic surfactants such as polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, and sorbitan fatty acid ester.
  • Pharmaceutical adjuvants include, for example, water-soluble polymers such as polyvinyl alcohol, polyvinylinolepyrrolidone, etc., polysaccharides such as gum arabic, alginic acid and salts thereof, CMC (carboxymethylcellulose), xanthan gum, etc., and aluminum magnesium silique.
  • water-soluble polymers such as polyvinyl alcohol, polyvinylinolepyrrolidone, etc.
  • polysaccharides such as gum arabic, alginic acid and salts thereof, CMC (carboxymethylcellulose), xanthan gum, etc.
  • aluminum magnesium silique examples include inorganic substances such as alumina sol, preservatives, coloring agents, and stabilizers such as PAP (acid isopropyl phosphate) and BHT.
  • the application method of the compound of the present invention include foliage application, soil treatment, seed disinfection, and the like, and further, it can be used in any application method usually used by those skilled in the art.
  • the application rate of the active ingredient depends on the type of the target plant (crop, etc.), the type of the target disease, the degree of occurrence of the disease, the formulation, the application method, the application time may vary depending weather conditions, etc., per 1 are normally 0. 0 1 to 5 0 g, preferably 0. 0 5 to 1 0 8 Dearu.
  • the application concentration is 0.0001 to 3%, preferably 0.0005 to 1%.
  • the granules, etc. are applied without dilution.
  • the compound of the present invention can be used as a fungicide for agricultural and horticultural use in fields, paddy fields, orchards, tea gardens, meadows, turf, and the like. Can be expected to increase.
  • Other agricultural and horticultural fungicides that can be mixed are, for example, propiconazole, triadimenol, prochloraz, penconazol, tebuconazo monole, funoresilazonole, giniconazo monole, bromconazo monole, epokishikonazo.
  • benzimidazole fungicides such as carbendazim, benomyl, thiabendazoline, thiophanate methyl
  • the compound of the present invention can be mixed with or used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, herbicides, plant growth regulators, and fertilizers.
  • insecticide and / or acaricide and / or nematicide examples include, for example, fenitrothion [ ⁇ , ⁇ -dimethyl ⁇ - (3-methynole-14-nitrophenyl) phosphorothioate], phenylion [0 ,, —Dimethyl ⁇ — (3-Methyl-14- (methylthio) phenyl) phosphorothioate], diazinon [0, ⁇ —Jetyl ⁇ —2-isopropyl-16-methylpyrimidine-14-yl phosphorothioate], chlorpyrifos [0, ⁇ —Jetinole 0—3,5,6—Trichloro-1-2-pyridinole phosphorothioate], acephate (0, S—dimethylacetylphosphoramidothioate), methidathion (S—2,3-dihydro draw 5—medium) Toxic-2-oxo-1,3
  • Thiourea derivatives such as (2,6-diisopropynole-1-4-phenoxyphenyl) -N'-t-butynole compound, phenylhydrazole compounds, tebufenozide [N-t-butyl-N'- (4-Ethylbenzoyl) -1,5-dimethylbenzene hydrazide], 4-bromo-12- (4-chlorophenoxy) 1-1-ethoxymethylone 5-trifluorotrifluoromethylpyrrole-3-carbone Tolyl, bromopropylate [isopropyl 4, 4'-dibromobenzylate], tetradiphone [4-chloropheninole 2,4,5-trichloromouth phenylsnolephone], quinomethionate [S, S-6-methylquinoxaline] 2,3-diyldicarbonate], pulp pargite [2- (4-t-butylphenoxy) cyclohe
  • Plant diseases that can be controlled by the compound of the present invention include, for example, the following diseases.
  • Erysiphe graminis Erysiphe graminis
  • red force bi;
  • Hei Gabberella zeae
  • Pabinia Puccinia strni'ormis, P. graminis, P. recondita, P. hordei
  • Snow rot Snow rot (Typhula) sp., Micronectriella nivalis), Bark smut (Ustilago tritici, U.
  • Peach scab (Sclerotinia cinerea), scab (Cladosporium carpophi lum), phomopsis rot (Phoitiops is sp.),
  • Grape scab (El sinoe ampelina), ⁇ rot (Glomerel la cingulata), powdery mildew (Uncinula necator), sabi bun (Phakopsora ampelopsidis) Buch crot (Guignardia bi dwel lii), downy mildew (Plasmopara vi ticola) ⁇ Oyster anthracnose (Gloeosporium kaki), defoliation;) hei (Cercospora kaki,
  • Ring rot (Alternaria solani), Leaf blight (Cladosporium fulvum), Phytophthora infestans ⁇
  • Green onion rust (Puccinia al li i), soybean purpura (Cercospora kikuchi i) Black spot (Elsinoe glycines), Black spot (Diaporthe phaseolorum var. Sojae), Green bean anthracnose (Colletotrichum l indemthianum), Black sickness of Lackasey
  • Production Examples of the compound of the present invention and Production Examples of intermediates for producing the compound of the present invention are shown in Production Examples and Reference Production Examples.
  • the numbers of the compounds of the present invention are the compound numbers described in Tables 1 to 12 below.
  • Methyl 2- (5-odo-1-2-methinolephenoxy) 1-3-methoxy-12-propanoate 300 mg (0.862 mmo 1), feninoleboronic acid 126 mg (1.03 mmo 1 ), Tetra-n-butylammonium bromide 278 mg (0.862 mmo 1), potassium carbonate 276 mg (2.15 mmo 1), palladium acetate (II) 19.3 mg (0 .08 6 mm 0 1) and 3 ml of water were mixed and stirred at 70 ° C for 1 hour. The mixture was cooled to room temperature, diluted with t-butyl methyl ether, washed with water, dried (sodium sulfate), and concentrated under reduced pressure. The precipitated crystals were washed with n-hexane to obtain 50 mg of methyl 3-methoxy-2- (2-methyl-15-phenylphenoxy) -12-propanoate (Compound 1-1 of the present invention). .
  • Methyl 2- ⁇ 2-methinolay 5 (4,4,5,5-tetramethinolate 1,3,2-dioxoborolan-1-yl) phenoxy ⁇ -13-methoxy-1-2-probenoeet 200mg (0 5 74 mm o 1), 3-bromo-1- (4-pyrimidinolemethoxy) benzene153 mg (0.557 mmo 1), tripotassium phosphate hydrate 61 Omg (2.87 mm o 1) , ⁇ 1, 1'-bis (diphenylphosphino) phenoctene ⁇ dichloropalladium (II) methylene chloride complex 23.5 mg (0.029 mmo 1), palladium acetate (II) 6.4 mg (0.0 29 mmo 1) and 3 ml of ethylenedaricol dimethyl ether were mixed and stirred at 83 ° C for 5 hours.
  • Methyl 2- (5-bromo-1-2-methylphenoxy) _3-methoxy-1_2_propanoate 200 mg (0.631 mmo 1), 2- (trimethyltin) pyridine 229 mg (0.947 mmo 1), bis-1 ( Trienninophosphine para After mixing 22 mg (0.031 mmo 1) of di (II) dichloride, 5 Omg (0.629 mmo 1) of copper oxide (II) and 3 ml of ethylene glycol dimethyl ether, the mixture was stirred at 80 ° C for 6 hours. . The mixture was cooled to room temperature, diluted with ethyl acetate, washed with water, dried (sodium sulfate), and concentrated under reduced pressure. The residue was subjected to silica gel preparative thin-layer chromatography (n-hexane: ethyl acetate 2:
  • aqueous layer was adjusted to pH 4 with a 5% aqueous hydrochloric acid solution, and then extracted with ethyl acetate.
  • the organic layer was washed successively with water and saturated saline, dried (anhydrous sodium sulfate), concentrated, and crude methyl 3-hydroxy-12- ⁇ 2-methinolay 5-bromo-1-benzyl ⁇ acrylic acid 6.lg I got
  • Me represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group
  • Py represents a pyridyl group
  • B represents a pyridyl group.
  • n means a benzyl group. Also, n- is normal, i- is iso-, sec- is secondary, and t- is tertiary.
  • formulation examples are shown. The parts represent parts by weight, and the compounds of the present invention are indicated by the numbers shown in Tables 1 to 12 above.
  • Compound of the Present Invention 11 ! ⁇ 1— 1 28 and 2— :! 2 parts each of 2 to 128, synthetic 1 part hydrous silicon oxide, 2 parts calcium ligninsulfonate, 30 parts bentonite and 65 parts kaolin clay, pulverize and mix well, add water and knead well. Each granule is obtained by drying the granules.
  • Test example 1 Rice blast control test (preventive effect)
  • Plastic pots were filled with sandy loam, and rice (Nipponbare) was sown and grown in a greenhouse for 20 days. Thereafter, the compounds of the present invention 1-1, 1-23, 1-36, 1-40, 1-11, 1-13, 1-2, 2-1, 1-32, 1_51, 1-192, 1 1 9 1, 1—27, 1 1 25, 1 -6, 1 1 16, 1—45, 1 1 1 59, 1—1 1 1, 1—1 1 2, 1—68, 1—69, 1 1 62, 1—73, 1—72, 1—
  • Each of 2-83 and 1-78 was made into a flowable formulation according to Formulation Example 6, and was then given a predetermined concentration of water (500 ppm; however, compounds 1-45, 2-86, 2-82, 2-94 of the present invention). And 2_83 (200 ppm) and sprayed so that it adheres well to the rice leaf surface. After spraying, the plants were air-dried and sprayed with a suspension of the blast fungus. After inoculation, the plants were placed in a humid environment at 28 ° C for 6 days, and the control effect was investigated.
  • the compound of the present invention 1-1, 1-23, 1-136, 1-40, 1-11,1-113, 1-2, 2-1, 1-32, 1-151, 1-- 92, 1—91, 1—27, 1—25, 1—6, 1—16,
  • Test example 2 Wheat powdery mildew control test (Therapeutic effect)
  • a plastic pot was filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the wheat seedlings that had developed the second leaf were sprinkled with wheat powdery mildew spores and inoculated. After inoculation, they were placed in a greenhouse at 23 ° C for 2 days.
  • Compound 11 of the present invention Each of 1, 1, 23, 1-36, 1-40 and 1-32 was made into a flowable preparation according to Preparation Example 6, and then diluted with water to a predetermined concentration (500 ppm). Was sprayed on the leaves of wheat inoculated with the powdery mildew fungus so as to sufficiently adhere to the leaves. After spraying, and after 7 days under lighting, the control effect was investigated.
  • test example 3 Wheat powdery mildew control test (preventive effect)
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compounds of the present invention 1 1 1 1 1 1 1 1 1 1 1 1 1 2 1 2 1 1 1 51 1 92 1 1 91 1 27 1 25 1 6 1 1 16 1 5 9, 1—111, 1—1 12, 1—68, l-69 1—62, 1—73, 1—72, 1—86, 1—64, 1—66, 1—113, 1—1 15, 1—82, 1—94, 1—114, 2—3, 2—37, 2-68, 2—86, 2—91, 2— 82, 2-94, 2-83 and 1-78 were made into flowable agents according to Formulation Example 6, and then given a predetermined concentration (500 ppm; water) of the compound of the present invention 2-86, 2-82, 2-9 with water.
  • a predetermined concentration 500 ppm; water
  • the compounds of the present invention 1 1 1 1 1 1 1 1 1 1 1 1 3 1 2 1 2 1 2 1 2 1 1 1 1 1 2 1 2 1 2 1 2 1 2 1 2 1 2 1 — 59, 1— 1 1 1, 1— 1 12, 1—68, 1—69, 1—62, 1—73, 1—72, 1—86, 1—64, 1—66, 1—1 13 , 1—115, 1—82, 1—94, 1—1 14, 2—3, 2—37, 2—68, 2—86, 2
  • Test example 4 Wheat rust control test (preventive effect)
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compound of the present invention 1-1, 1-23, 1-36, 1-40, 1-11-1, 1-11, 1-12-2-1, 1-132, 1-151, 1-192, 1-1 91,
  • Each of 2-3, 2-37, 2-68, 2-86, 2_91, 2-82, 2-94, 2-83 and 1-78 was made into a floor veneer formulation according to Formulation Example 6, and then water was added. Dilute to the specified concentration (500 ppm; however, the compounds of the present invention 1-45, 2-86, 2-82, 2-94 and 2-83 are 200PPII1), and dilute it so that it adheres well to the wheat leaf surface. Foliage was sprayed. After spraying, the plants were air-dried and inoculated with spores of wheat leaf rust. After the seeding, they were first placed in a dark and humid environment at 23 ° C for 1 day, and then put in illumination for 6 days.
  • the compounds of the present invention 1_1, 1-23, 1-136, 1-140, 1_1 1, 1-13, 1-1-2, 2-1, 1-132, 1_51, 1-192, 1-91, 1 — 27, 1-25, 1-6, 1-16, 1-45, 1_59, 1- 1 1, 1—1 1 2, 1—68, 1—69, 1—6 2, 1—73, 1—7 2, 1—8 6, 1—64, 1—6 6, 1—1 1 3, 1—1 1 5, 1—8 2, 1—94, 1—1 1, 4, 2, 3, 2, 37, 2—68, 2—86, 2-91, 2—82, 2 —
  • Test Example 5 Wheat blight control test (preventive effect)
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • Compound of the present invention 1-1, 1-123, 1-136, 1-40, 1-32, 1-151, 1-192, 1-91, 1-127, 1-145, 1-1 66, 1 1 1 1
  • Plastic pots were filled with sandy loam, and wheat (Norin 73) was sown and grown in a greenhouse for 10 days.
  • the compound of the present invention 1-1, 1_23, 1-11-1, 1-113, 1-2, 1-132, 1-6, 1_59, 1-111, 1-11, 1- 68, 1—69, 1—62, 1—86, 1—64, 1—1 1 3, 2, —68 and
  • Test example 7 Grape downy mildew control effect test (preventive effect)
  • the compounds of the present invention 1_1, 1_23, 1-36, 1-40, 1-11, 2-11, 1-132, 1-151, 1-192, 1-91, 1-127, 1 1 25, 1 1 6, 1 1 16, 1 1 45, 1 -59, 1-1 1 1, 1-1 12, 1-1 68, 1-69, 1 -62 1-73, 1-72, 1 One 86, One One 64, One 66, One 113, One 115, One 82, One 94, One 114, Two Three, Two 37, Two 68,
  • Test example 8 Test for controlling the effect of cucumber powdery mildew (preventive effect) The pots were filled with sandy loam, sown with Kiuri (Sagami Hanjiro), and grown in a greenhouse for 12 days.
  • the compounds of the present invention 1-1, 1-23, 1-36, 1-40, 1-11-1, 1-1-3, 1-2, 2-1, 1-132, 1-51, 1-1 92, 1-19-1, 1-125, 1-6, 1-16-1, 1-59, 1-11-1, 1-11-12, 1-6, 1-169, 1-162, 1--
  • the lesion area on the plants in the 73, 1-72 and 1-86 treatment areas was less than 10% of the lesion area in the untreated area.
  • the compound of the present invention has excellent plant disease controlling effect.

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Abstract

L'invention concerne des dérivés d'acide acrylique représentés par la formule générale (1), des agents de lutte contre les maladies de plantes, contenant lesdits dérivés et utilisés en tant qu'ingrédient actif ; et un procédé de lutte contre des maladies de plantes. Dans ladite formule (1), W représente oxygène ou CH2 ; X représente CR4 ou azote ; Y représente CR5 ou azote ; R?1, R2 et R3¿ représentent chacun séparément hydrogène, halogéno, cyano, nitro, amino, hydroxyle, alkyle C¿1?-C10 éventuellement substitué, ou similaire ; et R?4, R5, R6, R7 et R8¿ représentent chacun séparément hydrogène, halogéno, alkyle C¿1?-C4, ou similaire.
PCT/JP2000/004080 1999-06-25 2000-06-22 Derives d'acide acrylique, leur utilisation et intermediaires pour leur preparation WO2001000562A1 (fr)

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WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
WO2020165403A1 (fr) 2019-02-15 2020-08-20 Syngenta Crop Protection Ag Dérivés de thiazole substitués par phényle en tant que composés microbiocides
WO2020193387A1 (fr) * 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
WO2020262648A1 (fr) 2019-06-28 2020-12-30 住友化学株式会社 Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
WO2021153758A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153760A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153759A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021176057A1 (fr) * 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
RU2817796C2 (ru) * 2019-03-22 2024-04-22 Сингента Кроп Протекшн Аг Фунгицидные соединения

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EP0212859A2 (fr) * 1985-08-22 1987-03-04 Imperial Chemical Industries Plc Fongicides

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EP0212859A2 (fr) * 1985-08-22 1987-03-04 Imperial Chemical Industries Plc Fongicides

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US11849728B2 (en) 2018-07-31 2023-12-26 Sumitomo Chemical Company, Limited Method for controlling soybean rust fungus having resistance against Qo site inhibitor
WO2020027214A1 (fr) 2018-07-31 2020-02-06 住友化学株式会社 PROCÉDÉ DE LUTTE CONTRE LA ROUILLE DU SOJA RÉSISTANT AUX INHIBITEURS DE Qo
WO2020079111A1 (fr) 2018-10-18 2020-04-23 Syngenta Crop Protection Ag Composés microbiocides
CN112789265A (zh) * 2018-10-18 2021-05-11 先正达农作物保护股份公司 杀微生物的化合物
CN112789265B (zh) * 2018-10-18 2024-03-08 先正达农作物保护股份公司 杀微生物的化合物
WO2020165403A1 (fr) 2019-02-15 2020-08-20 Syngenta Crop Protection Ag Dérivés de thiazole substitués par phényle en tant que composés microbiocides
CN113646295A (zh) * 2019-03-22 2021-11-12 先正达农作物保护股份公司 杀真菌化合物
WO2020193387A1 (fr) * 2019-03-22 2020-10-01 Syngenta Crop Protection Ag Composés fongicides
RU2817796C2 (ru) * 2019-03-22 2024-04-22 Сингента Кроп Протекшн Аг Фунгицидные соединения
EP3992178A4 (fr) * 2019-06-28 2023-10-04 Sumitomo Chemical Company, Limited Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
WO2020262648A1 (fr) 2019-06-28 2020-12-30 住友化学株式会社 Dérivé d'ester (méth)acrylique, et application et intermédiaire de production de celui-ci
WO2021153759A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153760A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021153758A1 (fr) * 2020-01-31 2021-08-05 住友化学株式会社 Composition de lutte contre les maladies des plantes, et procédé de lutte contre les maladies des plantes
WO2021176057A1 (fr) * 2020-03-05 2021-09-10 Syngenta Crop Protection Ag Compositions fongicides
CN115209735A (zh) * 2020-03-05 2022-10-18 先正达农作物保护股份公司 杀真菌组合物
US11993580B1 (en) 2023-12-01 2024-05-28 Neumora Therapeutics, Inc. Methods of treating neurological disorders

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