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WO1999008999A1 - Derives d'arylacetamide et bactericides a usage agricole et horticole - Google Patents

Derives d'arylacetamide et bactericides a usage agricole et horticole Download PDF

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Publication number
WO1999008999A1
WO1999008999A1 PCT/JP1998/003598 JP9803598W WO9908999A1 WO 1999008999 A1 WO1999008999 A1 WO 1999008999A1 JP 9803598 W JP9803598 W JP 9803598W WO 9908999 A1 WO9908999 A1 WO 9908999A1
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Prior art keywords
group
alkyl
alkoxy
halogen atom
substituted
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PCT/JP1998/003598
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English (en)
Japanese (ja)
Inventor
Katsumi Masuda
Tsuyoshi Asahara
Junko Suzuki
Atsushi Yasuda
Katsumi Furuse
Kazuo Kumakura
Ichiro Miura
Norimichi Muramatsu
Original Assignee
Kumiai Chemical Industry Co., Ltd.
Ihara Chemical Industry Co., Ltd.
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Application filed by Kumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd. filed Critical Kumiai Chemical Industry Co., Ltd.
Priority to AU86479/98A priority Critical patent/AU8647998A/en
Publication of WO1999008999A1 publication Critical patent/WO1999008999A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • 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
    • A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • 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
    • 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
    • A01N37/44—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 nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
    • C07C233/31—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Definitions

  • the present invention relates to an aryl amide derivative which is a novel compound not described in any literature, and a fungicide for agricultural and horticultural use containing the same as an active ingredient.
  • the present inventors synthesized various novel aryl acetate amide derivatives to develop a drug having a bactericidal activity superior to conventionally known bactericides, and examined the physiological activities thereof. However, they have found that they have an excellent bactericidal activity against rice blast and the like and do not cause any harm to useful crops, and have completed the present invention.
  • the present invention provides: (1) a general formula [1]
  • A represents X n phenyl group substituted by, which may be substituted also a 2-naphthyl group by 1 one naphthyl group or X n but it may also be substituted by X n
  • X is a halogen atom, C i-C6 alkyl group, C2-C6 alkenyl group, C2-C6 alkynyl group, C3-C6 cycloalkyl group, C1-C4 haloalkyl group, hydroxy group, Ci-C6 alkoxy Group, C2-C6 alkenyloxy group, C2-eg alkynyloxy group, C3-C6 cycloalkyloxy group, Ci-Czi halo Alkoxy group, phenoxy (in which the group C 1 through C 6 alkyl group, C 1 through C 4 Haroa alkyl group, C i ⁇ C 6 alkoxy group, Shiano group may be by connexion substituted nitro group or a halogen
  • Q is a cyano group or a group C OR 4
  • R 4 is a C i -C 6 alkyl group, a C 3 -C 6 cycloalkyl group, a C 1 -C 4 haloalkyl group, a C i -C 6 alkoxy group , C 2 to C s Arukeniruokishi groups, C 2 to C 6 Arukiniruokishi groups, C 3 to C 6 cycloalkyl Ruokishi group, amino groups, C ⁇ -C 6 alkylamino cyano group or a C 1 ⁇ C 6 dialkyl amino Represents a group).
  • an agricultural and horticultural killing agent containing these aryl amide derivatives as active ingredients. It is a fungicide.
  • the C ⁇ to C 6 alkyl group refers to a linear or branched alkyl group, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group.
  • the CQ-C6 cycloalkyl group includes, for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like.
  • the C-C4 haloalkyl group represents a linear or branched alkyl group substituted by a halogen atom, for example, a fluoromethyl group, a chloromethyl group, a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group. And a pentafluoroethyl group.
  • the C 2 to C 6 alkenyl group a straight-chain or branched alkenyl group, for example if a vinyl group, 1.
  • the C 2 to C 6 alkynyl group a linear or branched alkynyl group,
  • Echiniru group 1 one propynyl group, 2 _ propynyl group, 1-Petit group, 2-Bed ethynyl group, Examples thereof include a 3-butynyl group, a 4-methyl-1-pentynyl group, and a 3-methyl-1-pentynyl group.
  • An aralkyl group is a linear or branched C ⁇ ⁇ substituted by an aryl group.
  • Halogen atom means fluorine atom, chlorine atom, bromine atom and iodine atom.
  • the C ⁇ C 6 alkoxy group a straight-chain or branched alkoxy group, for example if main butoxy group, an ethoxy group, n- propoxy group, isopropoxy group, n- butoxy sheet group, isobutoxy group, sec —Butoxy group, tert —butoxy group, n-pen Tiloxy, isopentyloxy, n-hexyloxy and the like can be mentioned.
  • the C2-C6 alkenyloxy group represents a linear or branched alkenyloxy group, and examples thereof include an aryloxy group, an isopropyloxy group, a 2-butenyloxy group and the like.
  • the C 2 -C 6 alkynyloxy group represents a straight-chain or branched alkynyloxy group, and examples thereof include a 2-propynyloxy group, a 2-butynyloxy group, and a 3-butynyloxy group. .
  • Examples of the CQ-C6 cycloalkyloxy group include a cyclopropyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.
  • the C-C4 haloalkoxy group represents a straight-chain or branched-chain alkoxy group substituted by a halogen atom, for example, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a pentafluoroethoxy group. Group, etc.
  • C- 6- alkylthio refers to a linear or branched alkylthio, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio; Tert-butylthio group, n-hexylthio group and the like.
  • the C-C4 haloalkylthio group represents a straight-chain or branched-chain alkylthio group substituted by a halogen atom, such as fluoromethylthio, difluoromethylthio, trifluoromethylthio, and pentafluoro. And a loethylthio group.
  • Arukiruamino group a linear or branched Arukiruami amino group and table, for example Mechiruamino group, Echiruami amino group, n - propyl group, isopropyl Piruami amino group, n- Puchiruami amino group, Examples include an isobutylamino group, a sec-butylamino group, a tert-butylamino group, and an n-hexylamino group.
  • the C-C 6 dialkylamino group includes, for example, a dimethylamino group, a getylamino group, a dipropylamino group, a dibutylamino group and the like.
  • the C i -C 6 alkylcarbonyl group refers to a linear or branched alkyl carbonyl group, and examples thereof include an acetyl group, a propionyl group, a butyryl group, and an isoptyryl group.
  • the C 1 -C 6 alkoxycarbonyl group represents a linear or branched alkoxycarbonyl group, such as a methoxycarbonyl group, an ethoxyquin carbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, —Butoxycarbonyl group, isobutoxycarbonyl group, sec —butoxycarbonyl group, tert —butoxycarbonyl group, n—pentyloxycarbonyl group, n-hexyloxy group, etc. it can.
  • Some of the compounds of the present invention represented by the general formula [1] have one or more asymmetric carbon atoms in the molecule, and such compounds have optical isomers. Exists. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.
  • A is at Therefore substituted Fuweniru group or a 2-naphthyl group X n, R 1 is a chlorine atom, bromine atom, main butoxy group or R 2 is a methyl, ethyl or n-propyl group, and R 3 is an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-methylthio group.
  • Q is cyano, methoxycarbonyl, ethoxycarbonyl or acetyl;
  • X is fluorine; Chlorine atom, bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, trifluoromethyl group, methoxy group, ethoxy group Group, n-propoxy group, isopropoxy group, difluoromethyoxy group, trifluoromethyoxy group, phenoxy group, methylthio group, ethylthio group, isopropylthio group, dimethylamino group, getylamino group or phenyl group, and n is 1 to Compounds that are integers of 2 can be mentioned.
  • the compound of the present invention represented by the general formula [1] can be produced, for example, according to the following production method. Manufacturing method 1
  • the compound of the present invention [1] is prepared by converting an aryl acetic acid derivative represented by the general formula [2] to an amide represented by the general formula [3] by using a condensing agent, if necessary, in the presence of a catalyst and a catalyst or a base. It can be produced by reacting with carboxylic acids.
  • This reaction is usually performed in a solvent.
  • a solvent that can be used any solvent that does not inhibit the reaction may be used.
  • examples include pentane, hexane, heptane, cyclohexane, petroleum ether, rigoin, hydrocarbons such as benzene, toluene, xylene, dichloromethane, dichloromethane, and the like.
  • Halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, carbon benzene, and dichlorobenzene; ethers such as getyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane Ketones such as aceton, methylethyl ketone, methyl isobutyl pyrketone, and methyl isobutyl ketone; acetate esters such as methyl acetate and ethyl acetate; nitritols such as acetonitrile and propionitol; or dimethyl sulfoxide , N, N Can have use dimethylformamidine de, a non-pro ton polar solvent or a mixed solvent combining solvents selected from these sulfolane.
  • ethers such as getyl ether, diisopropyl ether, ethylene glycol dimethyl
  • condensing agent examples include 1-ethyl-3- (3-dimethylaminopropyl) force rubodiimid hydrochloride, N, ⁇ '-dicyclohexylcarbodiimide, carbonyldiimidazole, and 2-chloro-1,3-dimethylimidazolyl. ⁇ Muclide, etc.
  • Examples of the catalyst include 4-dimethylaminopyridine, 1-hydroxybenzotriazole, dimethylformamide and the like.
  • the base those generally used in this type of reaction can be used.
  • sodium hydroxide alkaline metal hydroxides such as hydroxide Alkaline earth metal hydroxides such as shim, sodium carbonate, alkaline metal carbonates such as carbonated lime, or triethylamine, trimethylamine, N, N-dimethylaniline, pyridine, N Organic bases such as —methylbiperidine, 1,5-diazabicyclo [4. And tertiary amines such as triethylamine, pyridine and N-methylbiperidine.
  • the reaction is carried out at a temperature of -50 ° C (: to 150 ° C, preferably 0 to 60 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • a compound represented by the general formula [2] can be synthesized by a known method [for example, Journal of Pharmaceutical Chemical Society, Vol. 82, pp. 4062 (1960); 0 rganic Synthesis, The method can be produced by the method described in Vol. 6, page 403 (1988) :) or a method analogous thereto.
  • the compound represented by the general formula [3] can be synthesized by a known method [for example, 0 rganic Synthesis, Vol. 3, p. 88 (1955); Journal of Medicinal Chemistry, Brother 9, Vol. 11 (1966); the method described in Tetrahedron Letters, vol. 17, p. 1455 (1977)] or a method analogous thereto. Manufacturing method 2
  • R i, R 2 , R 3 , A and Q represent the same meaning as described above, and L represents a halogen atom.
  • the compound of the present invention [1] is obtained by converting an aryl acetate hydride represented by the general formula [4] to a salt. It can be produced by reacting with an amine represented by the general formula [3] in the presence of a group.
  • This reaction is usually performed in a solvent.
  • Any solvent that does not inhibit the reaction may be used, for example, hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, lignin, benzene, toluene, xylene, and the like. Dicro.
  • Halogenated hydrocarbons such as methane, dichloroethane, chloroform, carbon tetrachloride, carbon benzene, dichlorobenzene, ethers such as dimethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, and dioxane; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl isobutyl ketone, acetates such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, or N Non-protonic polar solvents such as N, N-dimethylformamide, sulfolane and the like, or a mixed solvent combining solvents selected therefrom can be used.
  • ethers such as dimethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetra
  • alkaline metal hydroxides such as sodium hydroxide and hydroxylated lime
  • alkaline earth metal hydroxides such as calcium hydroxide
  • alkaline metal carbonates such as sodium carbonate and carbonated lime Salts
  • tertiary amines such as triethylamine and trimethylamine
  • organic bases such as pyridine and picoline; and the like, preferably, metal salts of alkali metal and tertiary amines.
  • the reaction is carried out at a temperature in the range of 150 to 150 ° C, preferably in the range of 0 to 60 ° C.
  • the reaction time is preferably 1 to 30 hours.
  • the aryl acetic acid halides represented by the general formula [4] can be obtained by converting the aryl acetic acid represented by the general formula [2] produced by the above-mentioned method into, for example, thionyl chloride, phosphorus pentachloride, It can be produced by reacting with a halogenating agent such as phosphorus bromide. Manufacturing method 3 0 RH— R l 'R l 0 R 2
  • R 1 ′ represents an alkoxy group, a cycloalkoxy group, a haloalkoxy group, an alkylthio group, an alkylamino group or a dialkylamino group. Represents a no group.
  • the compound [1] of the present invention is obtained by converting a monohalogenoaryl acetic acid amide represented by the general formula [1-1] into an alcohol, mercaptan or amine represented by the general formula [5] in the presence of a base. Can be produced by reacting with
  • Solvents that can be used may be any solvents that do not inhibit the reaction, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, rig-mouth, hydrocarbons such as benzene, toluene, xylene, and dichloromethane.
  • Halogenated hydrocarbons such as dichloroethane, chloroform, carbon tetrachloride, carbon benzene, dichlorobenzene, ethers such as acetyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, acetone, Ketones such as methyl ethyl ketone, methyl isobutyl ketone, and methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; alcohols such as methanol and ethanol.
  • Le ethers or dimethyl sulfoxide, N, N-dimethyl Chiruhorumuami de can be used non-pro ton polar solvent or a mixed solvent combining 3 ⁇ 4 medium is selected from these sulfolane.
  • alkaline metal hydroxides such as sodium hydroxide and hydroxyladium
  • alkaline earth metal hydroxides such as calcium hydroxide
  • alkaline metal carbonates such as sodium carbonate and lithium carbonate Salts
  • sodium bicarbonate alkaline metal hydrogencarbonates
  • sodium bicarbonate alkaline metal hydrogencarbonates
  • sodium bicarbonate alkaline metal hydrogencarbonates
  • sodium bicarbonate alkaline metal hydrogencarbonates
  • sodium bicarbonate alkaline metal hydrogencarbonates
  • sodium hydride alkaline metal hydrogencarbonates
  • alkaline metal hydrogencarbonates such as sodium bicarbonate
  • sodium hydride alkaline metal hydrides
  • sodium methylate sodium ethylate
  • Metal alkoxides such as tertiary amines such as triethylamine and trimethylamine or organic compounds such as pyridine Bases and the like are preferred, and preferred are alkali metal carbonates, alkali metal hydrides and alkali metal alcoholates.
  • the reaction temperature is 150. (: Up to 150 ° C., preferably 0 to 60 ° C.)
  • the reaction time is preferably 1 to 30 hours.
  • diastereomer B (highly polar substance) of the target compound was obtained.
  • Optical purity: diastereomer A 97.0% e.e., diastereomer B-99.296 e.e. (high-performance liquid chromatography, Daicel chiral cell OD)
  • isomer A indicates diastereomer A
  • isomer B indicates diastereomer B
  • isomer M indicates diastereomer mixture
  • Isomer RA refers to diastereomer A whose acid moiety is optically active (R)
  • isomer RB refers to diastereomer B whose acid moiety is optically active (R)
  • isomer RM The diastereomer mixture in which the acid moiety is the optically active substance (R) is shown.
  • Isomer SA indicates diastereomer A in which the acid moiety is optically active (S)
  • isomer SB indicates diastereomer B in which the acid moiety is optically active (S)
  • isomer SM indicates acid.
  • Diastereomer A refers to low-polarity diastereomer separated by silica gel column chromatography or high-performance liquid chromatography
  • diastereomer B refers to a high-polarity diastereomer similarly separated. Show.
  • A- 112 4-CI OCH3 CH 3 C 3 H 7 -i C00CH 3 M 1.5097
  • the agricultural and horticultural fungicide of the present invention comprises an aryl amide derivative represented by the general formula [1] as an active ingredient.
  • the active ingredient can be used in an appropriate dosage form depending on the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant and the like can be added to the active ingredient.
  • Suitable carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, isopropyl alcohol, xylene, cyclohexanone, and methyl naphthalene.
  • liquid carriers such as Surfactants and dispersants include, for example, dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, Examples include polyoxyethylene sorbitan monoalkylate. Examples of the auxiliary include carboxymethylcellulose and the like. These preparations are diluted to an appropriate concentration and sprayed or applied directly.
  • the fungicide for agricultural and horticultural use of the present invention can be used by foliage application, soil application or water surface application.
  • the compounding ratio of the active ingredient is appropriately selected according to need, but it is appropriate to use 0.1 to 20% (by weight) for powders and granules, and 5 to 80% (by weight) for emulsions and wettable powders. is there.
  • the application rate of the agricultural and horticultural fungicide of the present invention varies depending on the type of the compound used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form used, and the like.
  • the active ingredient when used as such as powders and granules, the active ingredient may be appropriately selected from the range of O.lg to 5 kg, preferably lg to 1 kg, per 10 liter.
  • liquid form such as emulsions and wettable powders, it is appropriate to appropriately select from the range of 0.1 ppm to 10,000 ppm, preferably 1 to 3, OOO ppm.
  • the compound according to the present invention can control plant diseases caused by fungi belonging to algal fungi (Oomycetes), ascomycetes (Ascomycetes), incomplete fungi (Deuteromycetes), and basidiomycetes (Basidiomycetes) by the above-mentioned application forms.
  • fungi belonging to algal fungi Olemycetes
  • ascomycetes Ascomycetes
  • Deuteromycetes incomplete fungi
  • Basidiomycetes Basidiomycetes
  • the compound of the present invention may be mixed with an insecticide, another fungicide, a herbicide, a plant growth regulator, a fertilizer *, etc., if necessary.
  • the formulation method will be specifically described with reference to typical examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.
  • An emulsion was prepared by uniformly dissolving 30% of the compound (A-65), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene.
  • A- 32 B a 9 V a ⁇ 9-va 29 -V e ⁇ 9-V a 09-V a 6 S-V a 89-V
  • Rice seedlings of 1.5 foliage stage were transplanted into four white spots in 9 cm diameter white porcelain pots and grown in a greenhouse.
  • the wettable powder prepared according to Formulation Example 2 at the 2.5 leaf stage was subjected to water application to the pot such that the active ingredient concentration was 300 g per 10 ares.
  • a conidia suspension of rice blast fungus (Pyricu 1 ariaoryzae) was spray-inoculated and immediately placed in a moist chamber at 25 ° C for 24 hours. Then, they were transferred to a greenhouse, and 5 days after the inoculation, the number of lesions on the highest leaf at the time of the inoculation was examined.
  • the control value was determined by Equation 1, and the results of evaluation based on the criteria in Table 29 are shown in Tables 34 to 35.
  • a wettable powder prepared according to Formulation Example 2 was diluted with water to a seedling seedling having four true leaves developed so that the active ingredient concentration would be 500 ppm, and 20 m1 per pot Sprayed. After air-drying, a spore suspension of the scab of apple scab (Venturiainaequa 1 is) was inoculated by spraying and immediately placed in a moist chamber at 22 ° C for 48 hours.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

L'invention porte sur des dérivés d'arylacétamide de formule générale (1) et des bactéricides à usage agricole et horticole. Dans la formule (1) A est un phényle à substitution Xn ou analogue; R1 est halogéno, C¿1?-C6 alkoxy ou analogue; R?2 et R3¿ sont chacun alkyle ou analogue; Q est cyano ou analogue; X est alkyle, alkoxy, halogéno, haloalkyle ou analogue; et n est un entier de 1 à 3. Lesdits bactéricides tout en combattant efficacement la piriculariose du riz, la tavelure de la pomme etc. ne causent aucun dommage aux récoltes, et ont un excellent effet résiduel et une très bonne résistance à la pluie, d'où leur intérêt pour l'agriculture et l'horticulture.
PCT/JP1998/003598 1997-08-13 1998-08-12 Derives d'arylacetamide et bactericides a usage agricole et horticole WO1999008999A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU86479/98A AU8647998A (en) 1997-08-13 1998-08-12 Arylacetamide derivatives and bacteriocides for agricultural and horticultural use

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP9/231761 1997-08-13
JP23176197 1997-08-13

Publications (1)

Publication Number Publication Date
WO1999008999A1 true WO1999008999A1 (fr) 1999-02-25

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PCT/JP1998/003598 WO1999008999A1 (fr) 1997-08-13 1998-08-12 Derives d'arylacetamide et bactericides a usage agricole et horticole

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AU (1) AU8647998A (fr)
WO (1) WO1999008999A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8129355B2 (en) 2002-07-05 2012-03-06 Intrexon Corporation Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63132867A (ja) * 1986-08-29 1988-06-04 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ アリールオキシカルボン酸誘導体及びその製造法
JPH08151364A (ja) * 1994-02-18 1996-06-11 Nissan Chem Ind Ltd 含窒素環状化合物および除草剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63132867A (ja) * 1986-08-29 1988-06-04 シエル・インターナシヨネイル・リサーチ・マーチヤツピイ・ベー・ウイ アリールオキシカルボン酸誘導体及びその製造法
JPH08151364A (ja) * 1994-02-18 1996-06-11 Nissan Chem Ind Ltd 含窒素環状化合物および除草剤

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8129355B2 (en) 2002-07-05 2012-03-06 Intrexon Corporation Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
US9802936B2 (en) 2002-07-05 2017-10-31 Intrexon Corporation Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex

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