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WO1997019908A1 - Derives de phenylalanine, substances optiquement actives, leurs sels ou composes de coordination, et leur utilisation en tant que fongicides - Google Patents

Derives de phenylalanine, substances optiquement actives, leurs sels ou composes de coordination, et leur utilisation en tant que fongicides Download PDF

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Publication number
WO1997019908A1
WO1997019908A1 PCT/JP1996/003484 JP9603484W WO9719908A1 WO 1997019908 A1 WO1997019908 A1 WO 1997019908A1 JP 9603484 W JP9603484 W JP 9603484W WO 9719908 A1 WO9719908 A1 WO 9719908A1
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group
groups
alkyl
phenyl
halo
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Inventor
Naoya Yamamoto
Koji Umimoto
Tsutomu Nishiguchi
Koji Baba
Tatsuo Tabuchi
Masanori Yoshida
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Nihon Nohyaku Co Ltd
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Nihon Nohyaku Co Ltd
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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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
    • 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
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to phenylalanine derivatives, salts thereof, their optically active
  • JP-A-49-109536 describes phenylalanine
  • the present invention provides novel fungicides for fruit gardening used for controlling
  • the present invention relates to fungicides for fruit gardening containing as an active ingredient any of phenylalanine derivatives represented by the following general formula (I), salts thereof, and their optically active substances or coordination compounds:
  • R 1 is a hydrogen atom or a (C 1 -C 8 )alkyl group
  • R 2 is a hydrogen atom; a (C 1 -C 8 )alkyl group; a (C 1 -C 6 )alkoxycarbonyl group; an unsubstituted (C 1 -C 6 )alkylcarbonyl group; a substituted (C 1 -C 6 )alkylcarbonyl group having as the substituent(s) one or more halogen atoms which may be the same or different; an unsubstituted phenyl(C 1 -C 6 )alkyl group; a substituted phenyl(C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )
  • substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups,
  • halo(C 1 -C 6 )alkoxy groups carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group; an unsubstituted phenylsulfonyl group; a substituted phenylsulfonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group
  • R 1 and R 2 being able to be taken together to represent a (C 1 -C 6 )alkylene group which may contain an oxygen atom or a nitrogen atom between adjacent carbon atoms of the carbon chain, or a phthaloyl group
  • R 3 is a group represented by the formula: OR 4
  • R 4 is a hydrogen atom; a (C 1 -C 18 )alkyl group; a halo(C 1 -C 8 )alkyl group; a (C 2 -C 6 )alkenyl group; a
  • phenyl(C 2 -C 6 )alkenyl group unsubstituted phenyl(C 2 -C 6 )alkenyl group; a substituted phenyl(C 2 -C 6 )alkenyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo ⁇
  • R 5 is a hydrogen atom; a (C 1 -C 8 )alkyl group; a cyclo(C 3 -C 8 )alkyl group; a (C 2 -C 6 )alkenyl group; a
  • R 6 is a hydrogen atom, a (C 1 -C 6 )alkyl group or a (C 2 -C 6 )alkenyl group, R 5 and R 6 being able to be taken together to represent a (C 1 -C 6 )alkylene group which may contain an oxygen atom or a nitrogen atom between adjacent carbon atoms of the carbon chain, and said (C 1 -C 6 )alkylene group being able to form a ring and have on the ring one or more substituents which may be the same or different and are selected from the group consisting of (C 1 -C 6 )alkyl groups, carboxyl
  • R 7 is a hydrogen atom, a (C 1 -C 6 )alkyl group, a cyclo(C 3 -C 8 )alkyl group, a cyclo(C 3 -C 8 )alkyl(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, a hydroxy(C 1 -C 6 )alkyl group, an amino(C 1 -C 6 )alkyl group, an unsubstituted phenyl(C 1 -C 6 )alkyl group, or a substituted phenyl(C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms. nitro group, cyano group, (C 1 -C 6 )alkyl groups,
  • R 8 is a hydrogen atom, a
  • (C 1 -C 6 )alkyl group an unsubstituted phenyl(C 1 -C 6 )alkyl group, or a substituted phenyl(C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group, and n is 0 or 1), X is a halogen atom, a nitro group, a cyano group, a hydroxyl group
  • R 1 is a hydrogen atom or a (C 1 -C 8 )alkyl group
  • R 2 is a hydrogen atom; a (C 1 -C 8 )alkyl group; a (C 1 -C 6 ) alkoxycarbonyl group; an unsubstituted (C 1 -C 6 )alkylcarbonyl group; a substituted (C 1 -C 6 )alkylcarbonyl group having as the substituent(s) one or more halogen atoms which may be the same or different; an unsubstituted phenyl(C 1 -C 6 )alkyl group; a substituted phenyl (C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )
  • substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups,
  • halo(C 1 -C 6 )alkoxy groups carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group; an unsubstituted phenylsulfonyl group; a substituted phenylsulfonyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group
  • R 1 and R 2 being able to be taken together to represent a (C 1 -C 6 )alkylene group which may contain an oxygen atom or a nitrogen atom between adjacent carbon atoms of the carbon chain, or a phthaloyl group
  • R 3' is a group represented by the formula:
  • R 4' is a hydrogen atom, a (C 3 -C 18 )alkyl group; a halo(C 1 -C 8 )alkyl group; a (C 2 -C 6 )alkenyl group; a (C 2 -C 6 )alkynyl group; a cyclo(C 3 -C 8 )alkyl group; a cyclo(C 3 -C 8 )alkyl(C 1 -C 6 )alkyl group; a hydroxy(C 1 -C 6 )alkyl group; a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group; a
  • halo(C 1 -C 6 )alkoxy groups carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group; a diphenyl(C 1 -C 6 )alkyl group; or an aromatic heterocyclic (C 1 -C 6 )alkyl group having on the ring one or more heteroatoms which may be the same or different and are selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom, provided that when each of R 1 and R 2 is a hydrogen atom, R 4' is other than hydrogen atom, tert-butyl group and benzyl group), a group represented by the formula:
  • R 5 is a hydrogen atom; a (C 1 -C 8 )alkyl group; a cyclo(C 3 -C 8 )alkyl group; a (C 2 -C 6 )alkenyl group; a
  • (C 2 -C 6 )alkynyl group an unsubstituted cyano(C 1 -C 6 )alkyl group; a substituted cyano(C 1 -C 6 )alkyl group having one or more substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups and phenyl group; a (C 1 -C 6 )alkoxy (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group; an unsubstituted amino(C 1 -C 6 )alkyl group; a substituted amino(C 1 -C 6 )alkyl group having 1 or 2 substituents which may be the same or different and are selected from (C 1 -C 6 )alkyl groups; an unsubstituted phenyl group
  • phenoxy(C 1 -C 6 )alkyl group unsubstituted phenoxy(C 1 -C 6 )alkyl group; a substituted phenoxy(C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups,
  • halo(C 1 -C 6 )alkoxy groups carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group; an unsubstituted phenyl(C 1 -C 6 )alkyloxy group; a substituted phenyl(C 1 -C 6 )alkyloxy group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylened
  • (C 1 -C 6 )alkyl group or a (C 2 -C 6 )alkenyl group R 5 and R 6 being able to be taken together to represent a (C 1 -C 6 )alkylene group which may contain an oxygen atom or a nitrogen atom between adjacent carbon atoms of the carbon chain, and said (C 1 -C 6 )alkylene group being able to form a ring and have on the ring one or more
  • substituents which may be the same or different and are selected from the group consisting of (C 1 -C 6 )alkyl groups, carboxyl group, ( C 1 -C 6 )alkoxycarbonyl groups, phenyl group, phenyl(C 1 -C 6 )alkyloxycarbonyl groups and phenyl(C 1 -C 6 )alkyloxy groups, provided that R 1 , R 2 , R 5 and R 6 are not hydrogen atoms at the same time, and that when R 1 is a tert-butoxycarbonyl group and R 5 is a benzyl group, R 6 is other than methyl group) or a group represented by the formula:
  • R 7 is a hydrogen atom, a (C 1 -C 6 )alkyl group, a cyclo(C 3 -C 8 )alkyl group, a cyclo(C 3 -C 8 )alkyl(C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group, a hydroxy(C 1 -C 6 )alkyl group, an amino(C 1 -C 6 )alkyl group, an unsubstituted phenyl(C 1 -C 6 )alkyl group, or a substituted phenyl(C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups,
  • R 8 is a hydrogen atom, a
  • (C 1 -C 6 )alkyl group an unsubstituted phenyl(C 1 -C 6 )alkyl group, or a substituted phenyl (C 1 -C 6 )alkyl group having on the ring 1 to 5 substituents which may be the same or different and are selected from the group consisting of halogen atoms, nitro group, cyano group, (C 1 -C 6 )alkyl groups, halo(C 1 -C 6 )alkyl groups, (C 1 -C 6 )alkoxy groups, halo(C 1 -C 6 )alkoxy groups, carboxyl group, (C 1 -C 6 )alkoxycarbonyl groups, (C 1 -C 6 )alkylenedioxy groups, phenyl group and phenoxy group, and n is 0 or 1, provided that when each of R 1 and R 2 is a hydrogen atom, R 7 is other than methyl group and isobutyl
  • (C 1 -C 18 )alkyl group means a linear or branched alkyl group of 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, 1-methylbutyl, 2-methylbutyl, 1, 2-dimethylpropyl, n-hexyl, isohexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 2,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
  • halo(C 1 -C 6 )alkyl group means a substituted alkyl group of 1 to 6 carbon atoms having as the substituent(s) one or more halogen atoms including fluorine atom, chlorine atom, bromine atom and iodine atom which may be the same or different, for example, trifluoromethyl or tetrafluoroethyl.
  • the cyclo(C 3 -C 6 )alkyl group includes cyclopropyl, cyclo-butyl, cyclopentyl, cyclohexyl, cycloheptyl, etc.
  • the (C 2 -C 6 )alkenyl group includes alkenyl groups of 2 to 6 carbon atoms, such as vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 4-butenyl, etc.
  • the alkynyl group includes alkynyl groups of 2 to 6 carbon atoms, such as ethenyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, etc.
  • the hydroxy(C 1 -C 6 )alkyl group includes hydroxymethyl, hydroxyethyl, etc.
  • the (C 1 -C 6 )alkoxy- (C 1 -C 6 )alkyl group includes methoxymethyl, ethoxymethyl, etc.
  • the (C 1 -C 6 )alkoxy(C 1 -C 6 )alkoxy(C 1 -C 6 )alkyl group includes methoxymethoxymethyl, ethoxymethoxymethyl, etc.
  • the (C 1 -C 6 )alkylthio(C 1 -C 6 )alkyl group includes methyl- thiomethyl, ethylthiomethyl, etc.
  • the carboxy( C 1 -C 6 )alkyl group includes carboxymethyl, carboxyethyl, etc.
  • the (C 1 -C 6 )alkoxycarbonyl(C 1 -C 6 )alkyl group includes methoxycarbonylmethyl, ethoxycarbonylmethyl, etc.
  • the cyano(C 1 -C 6 )alkyl group includes cyanomethyl, 1-cyano-1-methylethyl, etc.
  • the substituted amino(C 1 -C 6 )alkyl group having one or more substituents which may be the same or different and are selected from (C 1 -C 6 )alkyl groups includes methylaminomethyl, methylaminoethyl, dimethylaminomethyl, dimethylaminoethyl, etc.
  • the phenoxy(C 1 -C 6 )alkyl group includes phenoxymethyl. phenoxyethyl, etc.
  • the phenyl (C 1 -C 6 )alkyloxy (C 1 -C 6 )alkyl group includes, for example, substituted alkyl groups having a benzyloxy group, a phenethyloxy group or the like as the substituent.
  • the phenylthio(C 1 -C 6 )alkyl group includes phenylthiomethyl, phenylthioethyl, etc.
  • the aromatic heterocyclic substituted (C 1 -C 6 )alkyl group includes pyridylmethyl, pyrimidylmethyl, thienylmethyl, furylethyl, etc.
  • the phenyl (C 1 -C 6 )alkyloxy group includes benzyloxy, phenethyloxy, etc.
  • the (C 1 -C 6 )alkylene group which may contain an oxygen atom or a nitrogen atom between adjacent carbon atoms of the carbon chain may form, for example, a pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino group together with the nitrogen atom to which the
  • (C 1 -C 6 )alkylene group is bonded, and the pyrrolidino, piperidino, morpholino, thiomorpholino or piperazino group may be substituted by a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxycarbonyl group or a substituted or
  • the phenylalanine derivative of the general formula (I) of the present invention is an amino acid, it has D-form and L-form.
  • the phenylalanine derivative is a dipeptide, it has diastereomers as stereoisomers.
  • the phenylalanine derivative of the general formula (I) of the present invention includes mixtures of the above-mentioned optically active
  • the phenylalanine derivative of the general formula (I) of the present invention may form a salt.
  • the salt there can be usually exemplified salts with organic or inorganic bases or acids, for example, salts formed by addition of an acid such as hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, phosphoric acid, perchloric acid, thiocyanic acid, boric acid, formic acid, acetic acid, haloacetic acid, propionic acid, glycolic acid, citric acid, tartaric acid, succinic acid, gluconic acid, lactic acid, malonic acid, fumaric acid,
  • an acid such as hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, phosphoric acid, perchloric acid, thiocyanic acid, boric acid, formic acid, acetic acid, haloacetic acid, propionic acid, glycolic acid, citric acid, tartaric acid, succinic acid, glu
  • anthranilic acid benzoic acid, cinnamic acid, p-toluenesulfonic acid, alkylbenzenesulfonic acid,
  • naphthalenesulfonic acid sulfanilic acid or the like
  • salts with organic bases such as amines
  • salts with alkaline earth metal such as sodium, potassium, etc., or metals such as aluminum, etc.
  • alkaline earth metal such as sodium, potassium, etc., or metals such as aluminum, etc.
  • derivative of the general formula (I) of the present invention may form also a metal coordination compound, for example, a coordination compound with zinc, nickel, cobalt, copper, iron or the like.
  • each of R 1 and R 2 is preferably a hydrogen atom or a (C 1 -C 6 )alkyl group, particularly preferably a hydrogen atom
  • R 3 is preferably -OR 4 wherein R 4 is preferably a hydrogen atom, a (C 1 -C 6 )alkyl group, a cyclo(C 3 -C 8 )alkyl group, a phenyl(C 1 -C 6 )alkyl group or a substituted phenyl(C 1 -C 6 )alkyl group, particularly preferably a (C 1 -C 6 )alkyl group or a benzyl group
  • X is preferably a halogen atom.
  • the phenylalanine derivative of the general formula (I) of the present invention can be produced, for example, by any of the processes illustrated below.
  • R 1 , R 2 , R 3 , R 4 , R 5 and m are as defined above
  • R6 is the same as R 5 or is CH(R 7 )(CH 2 ) n COOR 8 (wherein R 7 , R 8 and n are as defined above)
  • R 1' is a benzyloxycarbonyl group or a tert-butoxycarbonyl group
  • Bn is a benzyl group
  • TsOH is p-toluenesulfonic acid
  • Hal is a halogen atom.
  • examples of inert solvent suitable for each production step are water and all inert solvents which are not changed under the reaction conditions.
  • inert solvents are alcohols (e.g. methanol, ethanol, n-propanol and isopropanol), ethers (e.g. diethyl ether, dioxane, diisopropyl ether, tetrahydrofuran, glycol monomethyl ether and glycol dimethyl ether), chlorinated hydrocarbons (e.g. chloroform and dichloromethane), amides (e.g.
  • reaction temperature ranges from -20oC to the boiling point of the solvent.
  • reaction time may be chosen in the range of 0.5 hour to 24 hours.
  • D,L-amino acids can be produced by a process based on the content of Journal of the Chemical Society, 1951, p.2071.
  • p-Toluenesulfonic acid salt of the phenylalanine derivative can be
  • Optically active substances of the phenylalanine derivative can be separated from their racemic modification by a high performance liquid chromatography according to a method described in
  • Optically active substances also can be prepared through optical resolution method using optically active amines or acids as a optically resoluting agent.
  • the starting compound i.e., the compound of the general formula (II) or (V) is a well-known
  • Bn and TsOH are as defined above, Et is an ethyl group, Ac is an acetyl group, Bzo is a benzyloxycarbonyl group, and Boc is a tert-butoxycarbonyl group.
  • the phenylalanine derivatives of the general formula (I) of the present invention are useful as agricultural fungicides and are excellent particularly as fungicides for fruit trees for controlling, for example, Alternaria leaf spot, scab and black spot.
  • the phenylalanine derivative and optionally an adjuvant are blended with a suitable inert carrier in a proper proportion and prepared into a suitable preparation form such as a solution, a suspension, an oil formulation, an emulsifiable concentrate, dust, granules, a wettable powder, tablets, pellets, a paste or an aerosol through dissolution, dispersion, suspension, mixing, impregnation, adsorption or sticking.
  • a suitable inert carrier any of solid, liquid and gaseous carriers may be used.
  • soybean flour there can be exemplified soybean flour, wood flour, bark flour, saw dust, powdered tobacco stalks, powdered walnut shells, bran, powdered cellulose, extraction residue of vegetables, powdered synthetic polymers or resins, clays (e.g. kaolin, bentonite, and acid clay), talcs (e.g. talc and
  • silica powders or flakes e.g. diatomaceous earth, silica sand, mica, synthetic silicates, and synthetic, high-dispersion silicic acid
  • activated carbon powdered sulfur, powdered pumice, calcined diatomaceous earth, ground brick, fly ash, sand, calcium carbonate powder, calcium phosphate powder and other inorganic or mineral powders
  • chemical fertilizers e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride and urea
  • carriers may be used alone or as a mixture thereof.
  • the liquid carrier is that which itself has solubility or which is without such solubility but is capable of dispersing an active ingredient with the aid of an adjuvant.
  • cyclohexanone ethers such as ethyl ether, dioxane, tetrahydrofuran and Cellosolve; aliphatic hydrocarbons such as gasoline and kerosene; aromatic hydrocarbons such as benzene, toluene, solvent naphtha and methylnaphthalene; halogenated hydrocarbons such as dichloroethane and chloroform; esters such as ethyl acetate and diisopropyl phthalate; amides such as dimethylformamide and dimethylacetamide; nitriles such as acetonitrile; and dimethyl sulfoxide.
  • ethers such as ethyl ether, dioxane, tetrahydrofuran and Cellosolve
  • aliphatic hydrocarbons such as gasoline and kerosene
  • aromatic hydrocarbons such as benzene, toluene, solvent naphtha and methylnaphthalene
  • the gaseous carrier includes, for example, Freon, butane gas, dimethyl ether, carbonic acid gas and LPG (liquefied petroleum gas).
  • the following adjuvants can be exemplified. They are used depending upon purposes and used alone or in combination in some cases, or need not be used at all.
  • surfactants such as polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene resinates, polyoxyethylene sorbitan monooleate, alkylaryl sorbitan monolaurates, alkylbenzenesulfonates, alkylnaphthalenesulfonates, ligninsulfonates and higher alcohol sulfate esters.
  • adjuvants such as casein, gelatin, starch, alginic acid, CMC, gum arabic, agar, polyvinyl alcohols, turpentine, bran oil, bentonite, lignin, and sulfite liquor.
  • adjuvants such as waxes, stearic acid and alkyl phosphates.
  • Adjuvants such as naphthalenesulfonic acid condensation products and phosphates may be used as a peptizer for dispersible products.
  • Defoaming agents such as silicon oils may also be added.
  • the applying dosage of the active ingredient, i.e., the phenylalanine derivative is varied depending on various factors such as a purpose, a plant to be treated, a growth state of the plant, tendency of disease occurence, weather, environmental conditions, a preparation form, an
  • the content of the active ingredient may be varied as required. In dusts or granules, the content is usually 0.5 to 20%. In emulsifiable concentrates, suspensions or wettable powders, the content is 0.1 to 90% .
  • the fungicide for fruit gardening containing the compound of the present invention as an active ingredient may be used in admixture with other ingredients
  • the desired effect of the present inventive fungicide for fruit gardening containing the compound of the present invention as an active ingredient can be obtained by applying the fungicide at a season at which the diseases are expected to occur, before their occurrence or at the time when their occurrence is confirmed.
  • Typical examples of the phenylalanine derivative of the general formula (I) of the present invention are given in Table 1 but they are not intended in any way to limit the scope of the present invention.
  • Et, Bn, Bzo, Boc and TsOH are as defined above, Me is a methyl group, i-Pr is an isopropyl group, i-Bu is an isobutyl group, t-Bu is a tert-butyl group, Ph is a phenyl group, Bz is a benzoyl group, and DSA is a dodecylbenzenesulfonic acid.
  • Q 1 through Q 7 denote the following substituents:
  • Table 2 shows NMR data of the compounds having a physical property expressed by the word "paste" in Table 1.
  • reaction mixture was poured into ice water and a saturated aqueous sodium hydrogencarbonate solution was added, and the desired compound was extracted with ethyl acetate.
  • the organic layer was dried and then concentrated under reduced pressure, and the crystals thus obtained were washed with hexane to obtain 0.26 g of crystals of the desired compound .
  • Each compound of the invention 50 parts Xylene 40 parts
  • An emulsifiable concentrate was prepared by mixing uniformly the above ingredients to effect dissolution.
  • Granules were prepared by mixing the above ingredients uniformly, and kneading the resulting mixture together with a suitable amount of water, followed by granulation and drying.
  • Formulation Example 5
  • Each compound of the invention 20 parts Mixture of kaolin and synthetic, 75 parts high-dispersion silicic acid
  • a wettable powder was prepared by mixing uniformly and grinding the above ingredients.
  • Potted apple plants were sufficiently sprayed with a 200 ppm liquid chemical containing each compound of the present invention as active ingredient. Twentyfour hours after the spraying, the plants were

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Cette invention concerne un dérivé de phénylalanine correspondant à la formule générale (I) où R1 représente H ou un groupe alkyle et R2 représente H, un groupe alkyle, un groupe alcoxycarbonyle, un groupe phénylalkyle ou analogue, R1 et R2 pouvant ensemble représenter un groupe alcylène qui peut contenir O ou N entre des atomes de carbone adjacents de la chaîne de carbone, ou encore un groupe phtaloyle; et R3 représente OR?4, N(R5)-R6¿ ou NHCH(R7)(CH2)nCOOR?8, R4, R5, R6, R7 et R8¿ étant tels que définis dans le descriptif. Cette invention concerne également un sel de ce composé, leurs substances optiquement actives ou leurs composés de coordination, ainsi qu'un nouveau fongicide pour la culture des fruits contenant l'un de ces éléments sous forme d'ingrédient actif.
PCT/JP1996/003484 1995-11-29 1996-11-28 Derives de phenylalanine, substances optiquement actives, leurs sels ou composes de coordination, et leur utilisation en tant que fongicides Ceased WO1997019908A1 (fr)

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WO2000044770A1 (fr) * 1999-01-28 2000-08-03 Chugai Seiyaku Kabushiki Kaisha Derives phenethylamine substitues
WO2002022844A1 (fr) * 2000-09-18 2002-03-21 Kaneka Corporation Derive de fluorophenyalanine opto-actifs et procede de production dudit derive
WO2003066576A1 (fr) * 2002-02-06 2003-08-14 Basf Aktiengesellschaft Derives de phenylalanine en tant qu'herbicides
WO2003092690A1 (fr) * 2002-04-30 2003-11-13 The Procter & Gamble Company Derives de n-acyle piperidine utilises comme ligands du recepteur de la melanocortine dans le traitement de troubles de l'alimentation
US6730671B2 (en) 1999-03-02 2004-05-04 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cathespin S
US6756372B2 (en) 1999-09-13 2004-06-29 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
US7115607B2 (en) 2001-07-25 2006-10-03 Amgen Inc. Substituted piperazinyl amides and methods of use
US7253172B2 (en) * 2001-06-20 2007-08-07 Merck & Co., Inc. Dipeptidyl peptidase inhibitors for the treatment of diabetes
RU2394560C2 (ru) * 2005-07-19 2010-07-20 Дайити Санкио Компани, Лимитед Замещенное пропанамидное производное и фармацевтическая композиция, содержащая такое производное
AU2012202459B2 (en) * 2004-03-15 2014-06-12 Janssen Pharmaceutica, N.V. Novel compounds as opioid receptor modulators
US8772325B2 (en) 2004-03-15 2014-07-08 Janssen Pharmaceutica, N.V. Compounds as opioid receptor modulators
WO2018042425A1 (fr) * 2016-08-28 2018-03-08 The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization (Aro) (Volcani Center) Procédé de lutte contre les infections fongiques chez les plantes
US10173971B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10173981B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10172354B2 (en) 2012-12-28 2019-01-08 Dow Agrosciences Llc Synergistic fungicidal mixtures for fungal control in cereals
US10182568B2 (en) 2014-12-30 2019-01-22 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10188109B2 (en) 2014-12-30 2019-01-29 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US10433555B2 (en) 2014-12-30 2019-10-08 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
CN111517971A (zh) * 2020-05-14 2020-08-11 无锡市第二人民医院 一种抗真菌化合物、合成方法及其应用
US10793594B2 (en) 2017-04-19 2020-10-06 Indiana University Research And Technology Corporation Antimicrobial compounds and/or modulators of microbial infections and methods of using the same
US10919844B2 (en) 2015-08-14 2021-02-16 Indiana University Research And Technology Corporation Antibacterials and/or modulators of biofilm formation and methods of using the same
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
WO2023128033A1 (fr) * 2021-12-31 2023-07-06 (주)앰틱스바이오 Nouvelle composition antifongique pour inhiber la production de biofilm de champignons infectieux
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals
CN119798200A (zh) * 2024-12-11 2025-04-11 中山大学 一种l-苯丙氨酸衍生物类酪氨酸酶抑制剂及其制备方法
US12281076B2 (en) 2019-10-18 2025-04-22 Corteva Agriscience Llc Process for synthesis of picolinamides

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WO2000044770A1 (fr) * 1999-01-28 2000-08-03 Chugai Seiyaku Kabushiki Kaisha Derives phenethylamine substitues
US7553969B1 (en) 1999-01-28 2009-06-30 Chugai Seiyaku Kabushiki Kaisha Substituted phenethylamine derivatives
US6730671B2 (en) 1999-03-02 2004-05-04 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cathespin S
US7265132B2 (en) 1999-09-13 2007-09-04 Boehringer Ingelheim Pharmaceuticals Inc. Compounds useful as reversible inhibitors of cysteine proteases
US6756372B2 (en) 1999-09-13 2004-06-29 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
US6982272B2 (en) 1999-09-13 2006-01-03 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
US7056915B2 (en) 1999-09-13 2006-06-06 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
US7279472B2 (en) 1999-09-13 2007-10-09 Boehringer Ingelheim Pharmaceuticals Inc. Compounds useful as reversible inhibitors of cysteine proteases
US6858623B2 (en) 2000-09-08 2005-02-22 Boehringer Ingelheim Pharmaceuticals, Inc. Compounds useful as reversible inhibitors of cysteine proteases
WO2002022844A1 (fr) * 2000-09-18 2002-03-21 Kaneka Corporation Derive de fluorophenyalanine opto-actifs et procede de production dudit derive
US7253172B2 (en) * 2001-06-20 2007-08-07 Merck & Co., Inc. Dipeptidyl peptidase inhibitors for the treatment of diabetes
US7115607B2 (en) 2001-07-25 2006-10-03 Amgen Inc. Substituted piperazinyl amides and methods of use
US7560460B2 (en) 2001-07-25 2009-07-14 Amgen Inc. Substituted piperazines and methods of use
WO2003066576A1 (fr) * 2002-02-06 2003-08-14 Basf Aktiengesellschaft Derives de phenylalanine en tant qu'herbicides
WO2003092690A1 (fr) * 2002-04-30 2003-11-13 The Procter & Gamble Company Derives de n-acyle piperidine utilises comme ligands du recepteur de la melanocortine dans le traitement de troubles de l'alimentation
AU2012202459B2 (en) * 2004-03-15 2014-06-12 Janssen Pharmaceutica, N.V. Novel compounds as opioid receptor modulators
US8772325B2 (en) 2004-03-15 2014-07-08 Janssen Pharmaceutica, N.V. Compounds as opioid receptor modulators
US9205076B2 (en) 2004-03-15 2015-12-08 Janssen Pharmaceutica, N.V. Compounds as opioid receptor modulators
US9700542B2 (en) 2004-03-15 2017-07-11 Janssen Pharmaceutica Nv Compounds as opioid receptor modulators
US10213415B2 (en) 2004-03-15 2019-02-26 Janssen Pharmaceutica Nv Compounds as opioid receptor modulators
RU2394560C2 (ru) * 2005-07-19 2010-07-20 Дайити Санкио Компани, Лимитед Замещенное пропанамидное производное и фармацевтическая композиция, содержащая такое производное
US10172354B2 (en) 2012-12-28 2019-01-08 Dow Agrosciences Llc Synergistic fungicidal mixtures for fungal control in cereals
US10182568B2 (en) 2014-12-30 2019-01-22 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US11751568B2 (en) 2014-12-30 2023-09-12 Corteva Agriscience Llc Picolinamide compounds with fungicidal activity
US10173971B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10188109B2 (en) 2014-12-30 2019-01-29 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
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US10919844B2 (en) 2015-08-14 2021-02-16 Indiana University Research And Technology Corporation Antibacterials and/or modulators of biofilm formation and methods of using the same
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US11812746B2 (en) 2016-08-28 2023-11-14 The State Of Israel, Ministry Of Agriculture & Rural Development, Agricultural Research Organization (Aro) (Volcani Center) Method of controlling fungal infections in plants
CN109890205A (zh) * 2016-08-28 2019-06-14 以色列农业和农村发展部农业研究组织(范卡尼中心) 控制植物中的真菌感染的方法
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US12180163B2 (en) 2018-03-08 2024-12-31 Corteva Agriscience Llc Picolinamides as fungicides
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WO2023128033A1 (fr) * 2021-12-31 2023-07-06 (주)앰틱스바이오 Nouvelle composition antifongique pour inhiber la production de biofilm de champignons infectieux
CN119798200A (zh) * 2024-12-11 2025-04-11 中山大学 一种l-苯丙氨酸衍生物类酪氨酸酶抑制剂及其制备方法

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