JPH09208541A - New phenylalanine derivative, its optically active substance, its salts or complex compound, and use and usage of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new phenylalanine derivative represented by a specified formula, having an antagonistic effect on a disease damage to a fruit tree and a fungus of a human and an animal and useful as a bacteriocide for a horticultural fruit tree and an antifungal agent for a medical treatment. SOLUTION: This new phenylalanine derivative is represented by formula I [R<1> is H or a 1-8C alkyl; R<2> is H, a 1-8C alkyl, a 1-6C alkoxycarbonyl, a 1-6C alkylcarbonyl, etc.; R<3> ' is a group of the formula OR<4> (R<4> is H, a 3-18C alkyl, a 3-8C haloalkyl, etc.), etc.] and exemplified by N-(p-toluenesulfonyl)-4- fluorophenylaranine, etc. Moreover, the compound is obtained, for example, by the reaction, etc., using a compound represented by formula II [X is a halogen or nitro; (m) is 1-2] as a starting material under the existence of alcohols at the temperature between -20 deg.C and about the boiling temperature of the solvent for 0.5-24 hours.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a phenylalanine derivative, salts thereof, optically active compounds or complex compounds thereof,
The present invention relates to a fungicide for fruit trees and gardening containing the compound as an active ingredient, a method for using the same, and a medical antifungal agent containing the compound as an active ingredient.

[0002]

2. Description of the Related Art Phenylalanine derivatives are disclosed in JP-A-49-
Japanese Patent No. 109536 describes that a phenylalanine derivative has a controlling effect against rice blast and rice blight, and JP-A-60-116700 discloses kyotorphin as an analgesic. 37th
No. 07559 discloses N-acylphenylalanine amide as an anti-inflammatory agent and is disclosed in US Pat. No. 4,540,684.
Japanese Patent Publication No. 3 discloses a tripeptide as an anticancer agent,
JP-A-4-297492 discloses a tachykinin antagonist, JP-A-56-97257 discloses an enkephaline derivative as an analgesic, and JP-A-58.
JP-A-189121 discloses an insulin administration activator, and JP-A-58-32851 discloses an enkephalin derivative as an analgesic.
32851 discloses an enkephalin derivative as an analgesic agent and a tripeptide derivative as an antitumor agent, and Journal of Medicinal Chemistry 1983.
Vol. 26, page 1725, describes m-fluorophenylalanine derivatives. However, the usefulness of these compounds as a fungicide for fruit trees and gardening or as an antifungal agent for medical use is not described at all.

[0003]

Problems such as apple leaf spot and scab, pear black spot and the like are important diseases to be controlled in apple and pear fruit tree cultivation. The present invention provides a novel horticultural fungicide for fruit trees for controlling these diseases in fruit tree cultivation, and further, a medical antifungal useful for disinfecting human and animal limbs and fungal infections. It also provides an agent.

[0004]

The present invention has the general formula (I);

Embedded image [In the formula, R ¹ represents 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, a C ₁ -C ₆ alkylcarbonyl group, or a substituent substituted with one or more halogen atoms which may be the same or different.
C ₁ -C ₆ alkylcarbonyl group, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group , C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from an alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group, which may be the same or different, a halogen atom, Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl group having a ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,

Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenylsulfonyl group having 4 substituents on the ring,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group,
_{1 selected from a} C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 5 to 5 substituents on the ring, R ¹ and R ² are together a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom; It may also represent an interrupted C ₁ -C ₆ alkylene group or a phthaloyl group.

R ³ is of 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 C ₂ -C ₆ alkynyl group, a cyclo C _3- C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C _1- C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group , amino C ₁ -C ₆ alkyl group, the same or may be different C ₁ -C ₆ substituted amino C ₁ -C ₆ alkyl group having one to two substituents selected from an alkyl group, a cyano C ₁ - C ₆ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,

Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenyl C ₂ -C ₆ alkenyl group having one substituent on the ring, phenoxy C ₁ -C ₆ alkyl group, may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenoxy C ₁ -C ₆ alkyl groups having one substituent on the ring, phenylthio C ₁ -C ₆ alkyl groups, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenylthio C ₁ -C ₆ alkyl groups having ₁ substituent on the ring, phenylcarbonyl C ₁ -C ₆ alkyl groups, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ Alkyl group, halo C ₁ -C ₆ Alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl C ₁ -C ₆ alkyl group having on the ring, diphenyl C ₁ -C ₆ alkyl group or the same or different, and one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom An aromatic heterocycle C ₁ -C ₆ alkyl group having on the ring is shown. ),

Expression;

Embedded image N (R ⁵ ) —R ⁶ (R ⁵ is a hydrogen atom, C ₁ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl Base,
Cyano C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆
A cyano C ₁ -C ₆ alkyl group having one or more substituents selected from an alkoxy group or a phenyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alcoroxy C ₁ -C ₆ alkyl group, an amino C _1- C
₆ alkyl group, a substituted amino having 1 to 2 substituents be the same or different are selected from a good C ₁ -C ₆ alkyl group
C ₁ -C ₆ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy ₁ to 5 substituents selected from a group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. Substituted phenyl group having a ring, phenyl C ₁ -C ₆ alkyl group, may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group,
Carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C
₆ alkylenedioxy group, phenyl group, substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from phenoxy group on the ring, phenoxy C ₁ -C ₆ alkyl group,

Halogen atoms, which may be the same or different,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group on the ring, phenyl C ₁ -C ₆ alkyloxy group , May be the same or different, a halogen atom,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
Substituted phenyl C ₁ -C ₆ alkyloxy group having 1 to 5 substituents selected from C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group on the ring, or guanidyl C ₁
-C ₆ alkyl group, R ⁶ represents a hydrogen atom, a C ₁ -C ₆ alkyl group or a C ₂ -C ₆ alkenyl group, and R ⁵ and R ⁶ together form a C ₁ -C ₆ alkylene group. It is interrupted by a group or an oxygen atom or nitrogen atom indicates which may C ₁ -C ₆ alkylene group, C ₁ -C ₆ alkylene group to form a ring, which may be the same or different on the ring, C ₁ - C ₆ alkyl group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, phenyl group,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group or may have one or more substituents selected from phenyl C ₁ -C ₆ alkyl group. )

Or the formula;

Embedded image NHCH (R ⁷ ) (CH ₂ ) nCOOR ⁸ (wherein R ⁷ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a cyclo C ₃
-C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁
-C ₆ alkyl group, amino C ₁ -C ₆ alkyl group, phenyl C ₁
-C ₆ alkyl group, or may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents selected from the group consisting of ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups and phenoxy groups on the ring. _1- C ₆ alkyl group, R ⁸
Is a hydrogen atom, a C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group or the same or different, a halogen atom,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group on the ring, n is an integer of 0 or 1 Indicates. X is a halogen atom, nitro group, cyano group, hydroxyl group, amino group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, or a C ₁ -C ₆ alkoxy group, m is an integer of 1-2. ] A phenylalanine derivative represented by or a salt thereof, a fungicide for fruit and gardening containing an optically active substance or a complex compound thereof as an active ingredient, a method for using them, and a medical antifungal agent containing the compound as an active ingredient. There is a general formula (Ia) which is a novel compound which is included in the general formula (I) and is not described in the literature:

[0011]

Embedded image [In the formula, R ¹ represents 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, a C ₁ -C ₆ alkylcarbonyl group, or a substituent substituted with one or more halogen atoms which may be the same or different.
C ₁ -C ₆ alkylcarbonyl group, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group , C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from an alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group, which may be the same or different, a halogen atom, Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl group having a ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,

Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenylsulfonyl group having 4 substituents on the ring,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group, or the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenyl C ₁ having the substituent of
-C ₆ alkyloxycarbonyl group, and R ¹ and R ² together represent a C ₁ -C ₆ alkylene group, a C ₁ -C ₆ alkylene group interrupted by an oxygen atom or a nitrogen atom, or a phthaloyl group. It can also be shown.

R ³ 'is the formula;

Embedded image OR ⁴ ′ (R ⁴ ′ is a hydrogen atom, C ₃ -C ₁₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, cyclo C ₃ -C ₈ alkyl group, a cycloalkyl C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, a hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ Alkoxy C ₁ -C ₆ Alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, the same or may be different C ₁ -C ₆ substituted amino C ₁ -C ₆ alkyl group having one to two substituents selected from alkyl, cyano C ₁ -C ₆ alkyl group, phenyl group, may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,

Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenyl C ₂ -C ₆ alkenyl group having one substituent on the ring, phenoxy C ₁ -C ₆ alkyl group, may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl Group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenoxy C ₁ -C ₆ alkyl groups having one substituent on the ring, phenylthio C ₁ -C ₆ alkyl groups, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆
Alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
Substituted phenylthio C ₁ -C ₆ alkyl groups having ₁ substituent on the ring, phenylcarbonyl C ₁ -C ₆ alkyl groups, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ Alkyl group, halo C ₁ -C ₆ Alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl C ₁ -C ₆ alkyl group having on the ring, diphenyl C ₁ -C ₆ alkyl group,
Or an aromatic heterocycle C ₁ -C ₆ alkyl group which may be the same or different and has one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom on the ring. Where R
^{When 1} and R ² represent a hydrogen atom, R ⁴ 'is a hydrogen atom, tert
-Excluding butyl and benzyl groups. ),

Formula;

Embedded image N (R^Five) -R⁶  (R^FiveIs a hydrogen atom, C₁-C₈Alkyl group, cyclo C_Three-C₈A
Lucyl group, C_Two-C₆Alkenyl group, C_Two-C₆An alkynyl group,
Cyano C₁-C₆Alkyl groups, which may be the same or different,
Rogen atom, nitro group, halo C₁-C₆Alkyl group, C₁-C₆
One or more units selected from an alkoxy group or a phenyl group
Cyano C having a substituent₁-C₆Alkyl group, C₁-C₆Alkoki
C₁-C₆Alkycoxy C₁-C₆Alkyl group, amino C₁-C₆
Alkyl group, which may be the same or different, C₁-C₆Alkyl group
A substituted amino C having 1 to 2 substituents selected from₁
-C₆Alkyl group, phenyl group, same or different
, Halogen atom, nitro group, cyano group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group, carboxyl group, C₁-C₆Arco
Xycarbonyl group, C₁-C₆Alkylenedioxy group,
1-5 substitutions selected from nyl or phenoxy groups
A substituted phenyl group having a group on the ring, phenyl C₁-C₆Al
Kill groups, which may be the same or different, a halogen atom, nit
B group, cyano group, C₁-C₆Alkyl group, halo C₁-C₆Archi
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group,
Carboxyl group, C₁-C₆Alkoxycarbonyl group, C₁-C
₆Alkylenedioxy group, phenyl group or phenoxy group
Substituted 1 to 5 substituents on the ring selected from
Henil C₁-C₆Alkyl group, phenoxy C₁-C₆Alkyl
Group,

Halogen atoms, which may be the same or different,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group on the ring, phenyl C ₁ -C ₆ alkyloxy group , May be the same or different, a halogen atom,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
Substituted phenyl C ₁ -C ₆ alkyloxy group having 1 to 5 substituents selected from C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group on the ring, or guanidyl C ₁
Represents a -C ₆ alkyl group, R ⁶ represents a hydrogen atom, a C ₁ -C ₆ alkyl group or a C ₂ -C ₆ alkenyl group, and R ⁵ and R ⁶ together form a C ₁ -C ₆ alkylene group. or optionally interrupted by an oxygen atom or nitrogen atom indicates which may C ₁ -C ₆ alkylene group, C ₁ -C ₆ alkylene group to form a ring, which may be the same or different on the ring, C ₁ -C ₆ alkyl group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, phenyl group, phenyl C ₁ -C ₆ alkyloxycarbonyl group or phenyl
It can also have one or more substituents selected from C ₁ -C ₆ alkyloxy groups. However, R ¹ , R ² , R ⁵ and R ⁶
When R ¹ represents a tert-butoxycarbonyl group and R ⁵ represents a benzyl group, R ⁶ excludes a methyl group, except when R 2 and R ³ are simultaneously hydrogen atoms. )

Or the formula;

Embedded image NHCH (R ⁷ ) (CH ₂ ) nCOOR ⁸ (wherein R ⁷ is a hydrogen atom, a C ₁ -C ₆ alkyl group, a cyclo C ₃
-C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁
-C ₆ alkyl group, amino C ₁ -C ₆ alkyl group, phenyl C ₁
-C ₆ alkyl group, or may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents selected from the group consisting of ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups and phenoxy groups on the ring. _1- C ₆ alkyl group, R ⁸
May be a hydrogen atom, a C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group, or the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C _1- C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Represents a substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, wherein n is 0 or 1
Indicates an integer. However, when R ¹ and R ² represent a hydrogen atom,
R ⁷ with the exception of methyl and iso- butyl group, R ¹ is benzyloxycarbonyl group, when an integer of R ⁷ is a hydrogen atom and n 0, R ⁸ excluding the ethyl group. ). ] It is related with the phenylalanine derivative represented by these, its optically active substance, its chemically acceptable salt, or its complex compound.

[0018]

BEST MODE FOR CARRYING OUT THE INVENTION In the present invention, a C ₁ -C ₁₈ alkyl group is a linear or branched alkyl group having 1 to 18 carbon atoms,
For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, ter
t-butyl group, n-pentyl group, isopentyl group, neopentyl group, 1-methylbutyl group, 2-methylbutyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, 1-
Methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 1,1-dimethylbutyl group, 1,2-dimethylbutyl group, 2,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,
3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, 1,1,2-trimethylpropyl group, 1,2,2-trimethylpropyl group, 1-ethyl-1- The methylpropyl group, 1-ethyl-2-methylpropyl group and the like may be the same as or different from the halo C ₁ -C ₆ alkyl group, and one or more halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom. An alkyl group having 1 to 6 carbon atoms substituted with, for example, halo C ₁ -C ₆ alkyl such as trifluoromethyl and tetrafluoroethyl, and a cyclo C ₃ -C ₈ alkyl group is, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and the like, C ₂
The -C ₆ alkenyl group is, for example, vinyl, 1-propenyl,
An alkenyl group having 2 to 6 carbon atoms such as 2-propenyl, 1-butenyl, 2-butenyl, 4-butenyl,

Examples of the alkynyl group include ethenyl,
Examples of the hydroxy C ₁ -C ₆ alkyl group include alkynyl groups having 2 to 6 carbon atoms such as 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like, such as hydroxymethyl and hydroxyethyl. Is a C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, for example, methoxymethyl,
Examples of ethoxymethyl and the like, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyloxy C ₁ -C ₆ alkyl group include, for example, methoxymethoxymethyl, ethoxymethoxymethyl and the like, C ₁ -C ₆ alkylthio C ₁ -C ₆ As the alkyl group, for example, methylthiomethyl, ethylthiomethyl, etc., as the carboxy C ₁ -C ₆ alkyl group, for example, carboxymethyl, carboxyethyl, etc., as the C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group. Is, for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, etc., and as the cyano C ₁ -C ₆ alkyl group, for example, cyanomethyl, 1-cyano-1-methylethyl, etc., may be the same or different, C ₁ -C ₆ Substituted amino C ₁ having one or more substituents selected from alkyl groups
As the -C ₆ alkyl group, for example, methylaminomethyl,
Methylaminoethyl, dimethylaminomethyl, dimethylaminoethyl, etc., as the phenoxy C ₁ -C ₆ alkyl group, for example, phenoxymethyl, phenoxyethyl, etc.,

As the phenyl C ₁ -C ₆ alkyloxy C ₁ -C ₆ alkyl group, for example, an alkyl group substituted with benzyloxy, phenethyloxy, etc. can be used as phenylthio C ₁ -C ₆
Examples of the alkyl group include phenylthiomethyl and phenylthioethyl, and examples of the biphenyl C ₁ -C ₆ alkyl group include biphenylmethyl group and biphenylethyl group such as an aromatic heterocycle-substituted C ₁ -C ₆ alkyl group. Examples thereof include pyridylmethyl, pyrimidylmethyl, thienylmethyl, furylethyl and the like, and examples of the phenyl C ₁ -C ₆ alkyloxy group include benzyloxy, phenethyloxy and the like, and interruption at an oxygen atom or a nitrogen atom The optionally C ₁ -C ₆ alkylene group, together with the nitrogen atom to which it is attached, is, for example, pyrrolidino, piperidino,
Form morpholino, thiomorpholino, piperazino, etc.,
They can also be substituted with C ₁ -C ₆ alkyl groups, C ₁ -C ₆ alkoxycarbonyl groups or optionally substituted benzyl groups.

The phenylalanine derivative represented by the general formula (I) of the present invention exists in the D and L forms in the case of amino acids, and the diastereomers in the case of dipeptides as stereoisomers. It also includes those obtained by separating each optically active substance. Further, the general formula (I) of the present invention
The phenylalanine derivative represented by can also form a salt, and examples thereof generally include salts with an organic or inorganic base and an acid, such as hydrochloric acid, sulfuric acid, nitric acid, hydrobromic acid, phosphoric acid, and Chloric 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, anthranilic acid, benzoic acid, cinnamic acid, p
-Toluenesulfonic acid, alkylbenzenesulfonic acid,
Examples thereof include acid addition salts with naphthalene sulfonic acid, sulfanilic acid, etc., salts with organic bases with amines, etc., salts with alkaline earth metals such as sodium and potassium, or metals such as aluminum. Further, it may be a metal complex compound, and examples thereof include complex compounds with zinc, nickel, cobalt, copper, iron and the like.

The phenylalanine derivative represented by the general formula (I) of the present invention can be produced, for example, by the production method illustrated below. Scheme 1 Method A

Embedded image

Method B

Embedded image

Method C

Embedded image (In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and m are as defined above,
R ⁶ is R ⁵ or

Embedded image CH (R ⁷ ) (CH ₂ ) nCOOR ⁸ (R ⁷ , R ⁸ and n are the same as defined above), R ^{1 ′} is a benzyloxycarbonyl group or a tert-butoxycarbonyl group, and Bn is benzyl. Group, TsOH represents p-toluenesulfonic acid, and Hal represents a halogen atom. )

Suitable inert solvents for the individual production steps in this process are, for example, water or all inert solvents which do not change under the reaction conditions. These preferably include the following: Alcohols (eg,
Methanol, ethanol, propanol or isopropanol), ethers (eg diethyl ether, dioxane, diisopropyl ether, tetrahydrofuran, glycol monomethyl ether or glycol dimethyl ether), chlorinated hydrocarbons (eg chloroform, methylene chloride), amides (eg Dimethylformamide, dimethylamino or hexamethylphosphorylamide), glacial acetic acid, dimethylsulfoxide, acetonitrile or pyridine. The amount of the reagent in the reaction may be a catalytic amount to an excessive amount, preferably 1 equivalent. The reaction temperature can be from -20 ° C to the boiling point range of the inert solvent. The reaction time may be selected from the range of 0.5 hours to 24 hours.

Among the phenylalanine derivatives represented by the general formula (I), the D, L-amino acid is “Journal of
The Chemical Society, 1951, 2071
P., P-toluenesulfonate can be produced according to the description in “Basics and Experiments of Peptide Synthesis, page 43 (Maruzen Co., Ltd.)”, and the optically active substance is “Journal of Chromatography, Volume 405,” 145 (1887)
It can be separated from the racemate using high performance liquid chromatography according to the method described in 1. The raw material compound is a compound represented by the general formula (II) or the general formula (V) is a known substance. For example, the following general compounds as described in “Journal of the Chemical Society, 1951, p. It can be manufactured by a general manufacturing method.

Scheme 2 Production Method D

Embedded image (In the formula, X, m, Bn and TsOH are the same as above,
Et represents an ethyl group, Ac represents an acetyl group, Bzo represents a benzyloxycarbonyl group, and Boc represents a tert-butoxycarbonyl group. )

The phenylalanine derivative represented by the general formula (I) of the present invention, its optically active substance, its chemically acceptable salt, or its complex compound is useful as a fungicide for fruits and gardening and an antifungal agent for medical treatment. And, for example, as a bactericidal agent for fruit gardening such as spot leaf scab, scab, and scab.
It is useful as an antifungal agent for disinfecting limbs of humans and animals, and for treating and preventing mycosis and candidiasis caused by bacterial species of the genera Candida, Trichostiton and Cryptocox. Phenylalanine derivative represented by the general formula (I) of the present invention, its optically active substance, its chemically acceptable salt,
Alternatively, in order to formulate the complex compound thereof as a fungicide for fruit and gardening, this is mixed with a suitable inert carrier, if necessary together with an auxiliary agent, in an appropriate ratio, dissolved, dispersed, suspended, Mixing, impregnating, adsorbing or adhering, suitable dosage form such as solution, suspension, oil, emulsion, powder, granule, wettable powder,
It may be formulated into tablets, pellets, pastes, aerosols and the like. The inert carrier that can be used may be any of solid, liquid and gas, and as the material which can be a solid carrier, soybean flour, wood flour, bark flour, sawdust powder, tobacco stem flour, Walnut flour, bran, fibrin powder, residue after extraction of food extract, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay), talcs (eg talc, pyrophyllite), silicas ( For example, diatomaceous earth, silica sand, mica, synthetic silicate,
Synthetic highly dispersed silicic acid), activated carbon, sulfur powder, pumice, calcined diatomaceous earth, brick crushed product, fly ash, sand, calcium carbonate, inorganic mineral powder such as calcium phosphate, ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea, etc. Examples of the fertilizer include chemical fertilizer and compost, which are used alone or in the form of a mixture of two or more kinds.

The liquid carrier that can be used as a carrier is selected from those having a solvent ability per se, and those having no solvent ability but capable of dispersing an active ingredient compound with the aid of an auxiliary agent. However, these are used alone or in the form of a mixture of two or more kinds, for example, water,
Alcohols (eg methyl alcohol, isopropanol, ethylene glycol), ketones (eg acetone, cyclohexanone), ethers (eg ethyl ether, dioxane, tetrahydrofuran, cellosolve), aliphatic hydrocarbons (eg gasoline, kerosene) , Aromatic hydrocarbons (eg benzene, toluene,
Solvent naphtha, methylnaphthalene), halogenated hydrocarbons (eg dichloroethane, chloroform), esters (eg ethyl acetate, diisopropylphthalate), amides (eg dimethylformamide, dimethylacetamide), nitrites (eg acetonitrile), dimethylsulfoxide Etc. can be mentioned.
Examples of the gas carrier include freon, butane gas, dimethyl ether, carbon dioxide gas, LPG (liquefied petroleum gas) and the like.

Examples of the auxiliary agent include the following. These auxiliaries are used depending on the purpose. In some cases, two or more auxiliaries are used in combination, and in some cases, no auxiliaries are used at all. For the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compound,
For example, polyoxyethylene alkylaryl ether, polyoxyethylene alkyl ether, polyoxyethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monooleate, alkylallyl sorbitan monolaurate, alkylbenzene sulfonate, alkyl Surfactants such as naphthalene sulfonate, lignin sulfonate and higher alcohol sulfate ester salt can be used. Furthermore, for the purpose of dispersion stabilization, gluing and / or binding of the active ingredient compound, for example, casein, gelatin, starch, alginic acid, CMC, gum arabic, agar, polyvinyl alcohol, pine oil, bran oil, bentonite, lignin, sulfite. It is also possible to use auxiliary agents such as salt effluent. Adjuvants such as waxes, stearic acid, alkyl phosphates and the like can be used to improve the flowability of the solid product. As a peptizer for a suspending product, for example, an auxiliary agent such as a naphthalenesulfonic acid condensate or a phosphate can be used. It is also possible to add defoamers such as silicone oils.

When used as a bactericidal agent for fruit orchard of the present invention, the amount of active ingredient applied depends on various factors such as purpose, target crop, growing condition of crop, tendency of disease occurrence, weather, environmental conditions, dosage form, Although it varies depending on the application method, application place, application time, etc., it is appropriately selected from the range of 0.1 g to 1 kg per 10 ares. The blending ratio of the active ingredient can be adjusted according to need. When used as a powder or granule, it is usually 0.5% to 20%.
%, Or 0.1 for emulsions, suspensions or wettable powders
~ 90%. The fruit and horticultural fungicide containing the compound of the present invention as an active ingredient is further mixed with other agricultural and horticultural fungicides for the purpose of controlling the disease to be controlled, expanding the suitable control period, and for the purpose of reducing the dosage. It is also possible. Agro-horticultural fungicides containing the compound of the present invention as an active ingredient are used for the fruit and horticultural use of the present invention by treating them before the occurrence of the disease or at the time when the occurrence of the disease is confirmed, in accordance with the time when the occurrence of the disease is predicted. The intended effect of the fungicide is exhibited.

Next, a medical antifungal agent containing the phenylalanine derivative represented by the general formula (I) of the present invention, an optically active substance thereof, a pharmacologically acceptable salt thereof, or a complex compound thereof as an active ingredient is It is useful in the disinfection of human and animal limbs and in the treatment of fungal infections, for example Trichophyto.
n), Candida, Aspergis
llus), Cryptococcus and the like, and can be used for the treatment of local fungal infections, mucosal infections, systemic fungal infections and the like. The phenylalanine derivative represented by the general formula (I) of the present invention, an optically active substance thereof, a pharmacologically acceptable salt thereof, or a complex compound thereof alone or in a pharmacologically acceptable inert carrier or A composition comprising a diluent can be prepared and used in a dosage form suitable for oral or parenteral administration, for example, liquid, tablet, suppository, emulsifier, ointment, cream, lotion, poultice, etc. Auxiliaries, stabilizers, wetting agents or emulsifiers, buffers and other commonly used additives may also be included in these formulations as appropriate. The dose of the compound varies depending on symptoms, age, body weight, administration form, etc., but in the case of systemic treatment, it is usually 0.05 to 100 mg / kg body weight per adult per day.
Preferably, 0.5 to 50 mg can be administered once or in several divided doses. The concentration of the active ingredient in topical treatment is in the range of 0.001% to 5%, preferably 0.1% to 2%.

Representative examples of the phenylalanine derivative represented by the general formula (I) of the present invention, its optically active substance, its pharmacologically acceptable salt, or its complex compound are shown in Table 1. Is not limited to these. In the table, Et, Bn, Bzo, Boc and TsOH are the same as 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, and Ph is Phenyl group, Bz is benzoyl group and D
SA represents dodecylbenzene sulfonic acid. Also, Q ¹ ~
Q ⁷ represents the following substituent.

Embedded image

General formula (I):

Embedded image

[Table 1]

[0035]

[Table 2]

[0036]

[Table 3]

[0037]

[Table 4]

[0038]

[Table 5]

[0039]

[Table 6]

[0040]

[Table 7]

[0041]

[Table 8]

[0042]

[Table 9]

[0043]

[Table 10]

[0044]

[Table 11]

[0045]

[Table 12]

[0046]

[Table 13] The N of the compound whose physical properties are shown as a paste in Table 1 is shown below.
MR data are shown in Table 2.

[0047]

[Table 14]

[0048]

[Table 15]

[0049]

[Table 16]

[0050]

[Table 17]

[0051]

[Table 18]

[0052]

EXAMPLES The present invention will be specifically described below with reference to examples of the present invention, formulation examples, and test examples, but the present invention is not limited thereto. Embodiment 1 FIG. Production of N- (p-toluenesulfonyl) -4-fluorophenylalanine (Compound 1) 0.35 g of N- (p-toluenesulfonyl) -4-fluorophenylalanine benzyl ester was dissolved in 10 ml of ethanol, and 10% Pd-CO. Add 08g,
It was subjected to a hydrogenation reaction at room temperature and atmospheric pressure. After completion of the reaction, the catalyst was removed by filtration and the mixture was concentrated under reduced pressure. Ether was added for crystallization, and the crystals were filtered and washed with ether to obtain 0.24 g of the desired crystals. Physical property: m. p. 142-143 ° C Yield 87%

Embodiment 2 FIG. Preparation of 4-fluorophenylalanine cyclohexylamide acetate (Compound 6) 0.45 g of N- (benzyloxycarbonyl) -4-fluorophenylalanine cyclohexylamide was dissolved in a mixed solvent of ethanol, acetic acid and water (10 ml, 1 ml, 1 ml). 0.18 g of 10% Pd-C was added, and the mixture was subjected to hydrogenation reaction at room temperature and atmospheric pressure. After completion of the reaction, the catalyst was removed by filtration and the mixture was concentrated under reduced pressure. Hexane was added for crystallization, and the crystals were filtered and washed with hexane to obtain 0.26 g of desired crystals. Physical property: m. p. 115-116 ° C Yield 72%

Example 3 Preparation of N- (tert-butoxycarbonyl) -4-fluorophenylalanine benzylamide (Compound 9) 0.52 g of N- (tert-butoxycarbonyl) -4-fluorophenylalanine and 0.2 of triethylamine.
6 ml was dissolved in 15 ml of dry tetrahydrofuran, and 0.25 ml of isobutyl chlorocarbonate was added under ice cooling. 30
After stirring for a minute, 0.21 ml of benzylamine was added, and the mixture was further stirred at room temperature for 3 hours. After the reaction was completed, the reaction solution was poured into ice water, and the desired product was extracted with ethyl acetate. The organic layer was dried and concentrated under reduced pressure, and the obtained crystals were washed with hexane to give 0.49 g of the desired crystals. Physical property: m. p. 169-170 ° C 72% yield

Embodiment 4 FIG. Preparation of 4-fluorophenylalanine benzylamide (Compound 10) 5 ml of trifluoroacetic acid was added to 0.40 g of N- (tert-butoxycarbonyl) -4-fluorophenylalanine benzylamide, and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction solution was poured into ice water, saturated aqueous sodium hydrogen carbonate solution was added, and the target product was extracted with ethyl acetate.
The organic layer was dried and concentrated under reduced pressure, and the obtained crystals were washed with hexane to give 0.26 g of the desired crystals. Physical property: m. p. 67-68 ° C Yield 91%

Embodiment 5 FIG. Production of N- (benzyloxycarbonyl) -4-fluorophenylalanine-cyclohexylamide (Compound 19) N- (benzyloxycarbonyl) -4-fluorophenylalanine 1.0 g and triethylamine 0.44 ml
Was dissolved in 15 ml of dry tetrahydrofuran, and 0.42 ml of isobutyl chlorocarbonate was added under ice cooling. After stirring for 30 minutes, 0.4 ml of cyclohexylamine was added, and the mixture was further stirred at room temperature for 3 hours. After the reaction was completed, the reaction solution was poured into ice water, and the desired product was extracted with ethyl acetate. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystals were washed with hexane to obtain 0.78 g of desired crystals. Physical property: m. p. 183-184 ° C, yield 62%

Embodiment 6 FIG. Production of N- (p-toluenesulfonyl) -4-fluorophenylalanine benzyl ester (Compound 23) 4-Fluorophenylalanine benzyl ester p
-Dissolve 1.5 g of toluenesulfonate and 1.00 ml of triethylamine in 30 ml of dry dichloromethane,
0.71 g of p-toluenesulfonyl chloride was added under ice cooling. After stirring at room temperature for 24 hours, the reaction solution was poured into ice water and the desired product was extracted with dichloromethane. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystals were washed with ether to obtain 0.65 g of desired crystals. Physical property: m. p. 130-131 ° C Yield 45%

Example 7 Preparation of N- (4-tert-butylbenzyl) -4-fluorophenylalanine benzyl ester (Compound 27) 4-Fluorophenylalanine benzyl ester p
-Dissolve 1.0 g of toluenesulfonate and 0.65 ml of triethylamine in 15 ml of tetrahydrofuran,
0.53 g of 4-tert-butylbenzyl bromide was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the desired product was extracted with ethyl acetate, the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried and concentrated under reduced pressure, and the obtained oil was purified by silica gel column chromatography to give the desired product. 18 g was obtained. Physical Properties: Paste Yield 19% NMR [CDCl ₃ / TMS, δ value (ppm)] 1.31 (9H, s), 2.93 (2H, m), 3.55 (1H, t), 3.60 (1H, d), 3.
76 (1H, d), 5.07 (2H, m), 6.90 (2H, m), 7.05 (2H, m), 7.14
(2H, d), 7.24 (2H, m), 7.30 (2H, d), 7.35 (3H, m).

Embodiment 8 FIG. Production of N- (benzyloxycarbonyl) -4-fluorophenylalanine isoamyl ester (Compound 30) N- (benzyloxycarbonyl) -4-fluorophenylalanine 1.00 g, dimethylaminopyridine.
07 g and isoamyl alcohol 0.69 ml were dissolved in dry dichloromethane 15 ml, and 1- (3-dimethylaminopropyl) -3-ethyl-carbodiimide hydrochloride 0.66 g was added under ice cooling. After stirring at room temperature for 24 hours, the reaction solution was poured into ice water and the desired product was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, dried and concentrated under reduced pressure.
The obtained oil was purified by silica gel column chromatography to obtain 1.16 g of the desired product. Physical properties: Paste yield 95% NMR [CDCl ₃ / TMS, δ value (ppm)] 0.89 (6H, m), 1.12 (0.5H, m), 1.32 (0.5H, m), 1.48 (1H,
m), 1.60 (1H, m), 3.09 (2H, m), 3.93 (1H, m), 4.11 (1H, m),
4.62 (1H, m), 5.09 (2H, m), 5.22 (1H, d), 6.95 (2H, m), 7.
06 (2H, m), 7.35 (5H, m).

Embodiment 9 FIG. N- (benzyloxycarbonyl) -4-fluorophenylalanyl-piperidine-
Preparation of 4-carboxylic acid (compound 40) N- (benzyloxycarbonyl) -4-fluorophenylalanyl-piperidine-4-carboxylic acid ethyl ester 0.5 g was dissolved in water-containing ethanol 6 ml to obtain lithium hydroxide 0.05 g. Was added and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the reaction solution was poured into ice water and acidified with 1N hydrochloric acid, and the desired product was extracted with ethyl acetate. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystals were washed with ether to obtain 0.44 g of the desired product. Physical property: m. p. 180-181 ° C Yield 94%

Example 10. Preparation of N- (benzyloxycarbonyl) -4-fluorophenylalanyl-valine benzyl ester (Compound 44) N- (benzyloxycarbonyl) -4-fluorophenylalanine 2.0 g and triethylamine 2.62 ml
Was dissolved in 40 ml of dry tetrahydrofuran, and under ice cooling,
After adding 0.83 ml of isobutyl chlorocarbonate and stirring for 30 minutes, 2.39 g of valine benzyl ester p-toluenesulfonate was added, and the mixture was further stirred at room temperature for 24 hours. After the reaction was completed, the reaction solution was poured into ice water, and the desired product was extracted with ethyl acetate. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystal was washed with hexane to obtain 0.63 g of a target crystal. Physical property: m. p. 120-122 ° C Yield 20%

Example 11 Preparation of 4-fluorophenylalanyl-valine (Compound 45) N- (benzyloxycarbonyl) -4-fluorophenylalanyl-valine benzyl ester (1.00 g) was dissolved in ethanol, acetic acid and water (20 ml, (1 ml, 1 ml) was dissolved in a mixed solvent, 10% Pd-C (0.20 g) was added, and the mixture was subjected to hydrogenation reaction at room temperature and atmospheric pressure. After completion of the reaction, the catalyst was removed by filtration and the mixture was concentrated under reduced pressure. Ether was added for crystallization, and the crystals were filtered and washed with hexane to obtain 0.30 g of the desired product. Physical property: m. p. 142-145 ° C Yield 54%

Production Example 12. Production of 4-fluorophenylalanine (D, L-amino acid) (compound 168) 1.44 g of sodium metal was dissolved in 100 ml of ethanol, 12.38 g of diethyl acetamide malonate and 8.24 g of 4-fluorobenzyl chloride were added, and the mixture was stirred with heating for 7 hours. did. After the reaction was completed, ice water was added and the precipitated crystals were filtered and washed with water to obtain 14.0 g of crystals. The crystals were dissolved in 50 ml of 47% aqueous hydrogen bromide solution and stirred with heating for 8 hours. The reaction solution was neutralized with concentrated aqueous ammonia under ice cooling, and the precipitated crystals were filtered and washed with water to obtain 4.9 g of the desired crystals. Physical property: m. p. 253-257 ° C (decomposition) Yield 47
%

Production Example 13. 4-fluorophenylalanine benzyl ester p-toluenesulfonate (Ts
Preparation of OH salt, compound 181) 4-fluorophenylalanine 11.0 g, benzyl alcohol 80 ml, p-toluenesulfonic acid monohydrate 1
2.6 g of Dean-Stark in 60 ml of toluene
A water separator was attached and the mixture was heated and stirred for 6 hours. After the reaction, 100 ml of ether was added, and the precipitated crystals were filtered, and the obtained crystals were washed with hexane to give 23.2 g of the desired crystals.
I got Physical property: m. p. 158-159 ° C. Yield 87%,

Reference Example 1. Production of N- (benzyloxycarbonyl) -4-fluorophenylalanine 4.9 g of 4-fluorophenylalanine was dissolved in 30 ml of 2M sodium hydroxide solution, 5.0 g of benzyloxycarbonyl-chloride was added dropwise under ice cooling, and the mixture was mixed at 10 ° C. for 3 days. Stir for hours. After washing the reaction solution with ether, the aqueous layer was washed with 1
The mixture was acidified with N hydrochloric acid, and the desired product was extracted with ethyl acetate. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystals were washed with ether to obtain 7.13 g of desired crystals. Physical property: m. p. 120-122 ° C Yield 84%

Reference Example 2. Preparation of N- (tert-butoxycarbonyl) -4-fluorophenylalanine 10.1 g of 4-fluorophenylalanine was dissolved in 80 ml of 1M sodium hydroxide solution, and di-tert dicarbonate was added.
-Butyl 13.2 g was added dropwise under ice cooling, and the mixture was stirred at room temperature overnight. The reaction solution was washed with ether, the aqueous layer was acidified with citric acid, and the desired product was extracted with ethyl acetate. The organic layer was dried and then concentrated under reduced pressure, and the obtained crystals were washed with hexane to obtain 4.9 g of the desired product. Physical property: m. p. 253-257 ° C (decomposition) Yield 47
%

A prescription example is shown below. In the prescription example,
Parts are parts by weight. Formulation Example 1 Compound of the present invention 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and alkylbenzene sulfonic acid 10 parts The above components are uniformly mixed and dissolved to obtain an emulsion. Formulation Example 2 Compound of the present invention 0.5 part Xylene 0.8 part White kerosene 98.7 parts The above components are uniformly mixed and dissolved to obtain an oil agent.

Formulation Example 3 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above ingredients are uniformly mixed and pulverized to give a powder. Formulation Example 4 The compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium stearate 1 part
Dry to granules.

Formulation Example 5 Compound of the present invention 20 parts Mixture of kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above are uniformly mixed and pulverized to obtain a wettable powder. Formulation Example 6 Compound of the present invention 1 part Polyethylene glycol 400 99 parts The above components are uniformly mixed and dissolved to obtain a coating liquid agent.

Formulation Example 7 Compound of the present invention 2 parts Polyethylene glycol 400 49 parts Polyethylene glycol 4000 49 parts The above ingredients are uniformly mixed and dissolved under heating and then cooled to obtain an ointment. Formulation Example 8 Compound of the present invention 3 parts 1,2-Propanediol 5 parts Glycerol stearate 5 parts Whale wax 5 parts Isopropyl myristate 10 parts Polysorbate 4 parts The above mixture is heated and cooled, and then 68 parts of water under stirring. Add to make a cream.

Test Example 1 Control Test for Apple Leaf Spot Disease 200 ppm containing the compound of the present invention as an active ingredient in apple leaves
After thoroughly spraying the drug solution of
rnaria mali) spore suspension was spray treated. The area of the diseased spots was examined after leaving them in a humidity room at 15 ° C for 1 day and then in a constant temperature room at 15 ° C for 3 days to cause sufficient illness. . A control value 100% to 95% B control value 94% to 80% C control value 79% to 60% D control value 59% to 0% -no chemical damage The results are shown in Table 3.

Test Example 2 Control test against apple scab disease The apple of the present invention contains the compound of the present invention as an active ingredient 2
A chemical solution of 00 ppm was thoroughly sprayed, and one day after the treatment, a spore suspension of apple scab (Venturia inaequalis) was spray-inoculated. Leave it in a humid chamber at 17 ° C for 1 day, then
After leaving it in a constant temperature room at 7 ° C. for 10 days to cause sufficient disease, the area of diseased spots was investigated, and the effect was determined according to Test Example 1 in comparison with the untreated plot. The results are shown in Table 3.

[0073]

[Table 19]

[0074]

[Table 20]

[0075]

[Table 21]

[0076]

[Table 22]

[0077]

[Table 23]

[0078]

[Table 24]

[0079]

[Table 25]

[0080]

[Table 26]

Test Example 3 Candida albica
Antifungal activity against ns. C. in sterile saline. albicans IFO 12
70 yeast cells were suspended at 1.5 × 10 ⁵ cells / ml. BPMI 16 per 0.1m of inoculum
The mixture was diluted with 40 9.8 ml, and the compound was dissolved in DMSO to a concentration of 0.1 mg / ml and added to the inoculum bacterium solution. Static culture was carried out at 35 ° C. for 2 days. After culturing, 65
The culture turbidity was measured at 0 nm, and the growth inhibition rate was calculated according to the following formula. The results are shown in Table 4.

[Equation 1]

Test Example 4 Aspergillus fu
Antifungal activity against miguatus A in sterile saline (containing 0.1% Tween 80)
spergillus fumigatus TIMM
[0063] Yeast cells were suspended at 1 x 10 ⁵ conodia / ml. Compound is 0.1mg in DMSO
It was dissolved so that it became / ml. Yeast Nitrogene Base with with 0.1 ml of compound solution
out amino acids Glucose A
Gar 9.9 ml was added, and a plate medium was prepared in a sterile petri dish. The prepared bacterial solution was used to inoculate the compound-added medium using a micro stamper. After culturing at 37 ° C. for 2 days after inoculation, the culture turbidity was measured at 650 nm, and the growth inhibition rate was calculated according to the following formula. The results are shown in Table 4.

[Equation 2]

[0083]

[Table 27]

[0084]

[Table 28]

[0085]

[Table 29]

[0086]

[Table 30]

[0087]

[Table 31]

[0088]

[Table 32]

[0089]

INDUSTRIAL APPLICABILITY The compound of the present invention has an excellent controlling effect against diseases of fruit trees and fungi of humans and animals, and is useful as a bactericidal agent for fruit gardening and an antifungal agent for medical use.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical display location A61K 31/195 ADZ A61K 31/195 ADZ 31/215 31/215 31/27 31/27 31/275 31/275 31/495 31/495 31/535 31/535 38/00 9547-4H C07C 233/54 C07C 233/54 9547-4H 233/87 233/87 9547-4H 237/06 237/06 9547-4H 237/22 237/22 9547-4H 237/42 237/42 7419-4H 311/19 311/19 7419-4H 323/12 323/12 C07D 211/32 C07D 209/48 211/62 211/32 265/30 211/62 295/18 Z 265/30 A61K 37/02 295/18 C07D 209/48 Z // C07M 7:00 (72) Inventor Tatsuo Tabuchi Hyotaka-cho, Hidaka-cho, Wakayama 357 (72) Invention Person Masanori Yoshida 2-5-3 Koyodai, Hashimoto City, Wakayama Prefecture

Claims (9)

[Claims] 1. A compound represented by the general formula (Ia); [In the formula, R ¹ represents 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, a C ₁ -C ₆ alkylcarbonyl group, or a substituent substituted with one or more halogen atoms which may be the same or different.
C ₁ -C ₆ alkylcarbonyl group, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group , C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from an alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group, which may be the same or different, a halogen atom, Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl group having a ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C _1- 1 to 5 C ₆ alkoxy groups, halo C ₁ -C ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups or phenoxy groups Substituted phenylsulfonyl group having a substituent on the ring, phenyl
C ₁ -C ₆ alkyloxycarbonyl group, or may be the same or different, a halogen atom, a nitro group, a cyano group,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group,
_{1 selected from a} C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 5 to 5 substituents on the ring, R ¹ and R ² are together a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom; It may also represent an interrupted C ₁ -C ₆ alkylene group or a phthaloyl group. R ³ 'is a formula; OR ⁴ ' (R ⁴ 'is hydrogen atom, C ₃ -C ₁₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, cyclo C ₃ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group , C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy carbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, a substituted amino C ₁ -C having 1-2 substituents be the same or different are selected from a good C ₁ -C ₆ alkyl group ₆ alkyl group, cyano C ₁ -C ₆ alkyl group, phenyl group, may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenyl C ₂ -C ₆ alkenyl group having 1 to 5 substituents selected from the ring, phenoxy C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, phenylthio C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylthio C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, a phenylcarbonyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆
Substituted phenylcarbonyl C having 1 to 5 substituents on the ring selected from an alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _{A 1-} C ₆ alkyl group, a diphenyl C ₁ -C ₆ alkyl group, or an aromatic heterocycle which may be the same or different and has one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom on the ring. C ₁ -C
₆ Indicates an alkyl group. However, when R ¹ and R ² represent a hydrogen atom, R ⁴ ′ excludes a hydrogen atom, a tert-butyl group and a benzyl group. ), The formula; N (R ⁵ ) -R ⁶ (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, C ₂ -C ₆ alkynyl group,
Cyano C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆
Cyano C ₁ -C ₆ alkyl group having one or more substituents selected from alkoxy group or phenyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyloxy C ₁ -C ₆ alkyl group, amino C ₁ -C ₆
Alkyl group, substituted amino C ₁ having 1 to 2 substituents selected from the same or different C ₁ -C ₆ alkyl groups
-C ₆ alkyl group, phenyl group, may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, ₁ to 5 substituents selected from halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group on the ring Substituted phenyl group, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group,
Carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C
₆ alkylenedioxy group, phenyl group or substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from phenoxy group on the ring, phenoxy C ₁ -C ₆ alkyl group, the same or different Also good, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from alkylenedioxy group, phenyl group or phenoxy group on the ring, phenyl C ₁ -C ₆ alkyloxy group, the same or different Also good, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
R ₁ represents a substituted phenyl C ₁ -C ₆ alkyloxy group having 1 to 5 substituents selected from an alkylenedioxy group, a phenyl group or a phenoxy group on the ring, or a guanidyl C ₁ -C ₆ alkyl group, R ⁶ represents a hydrogen atom, a C ₁ -C ₆ alkyl group or a C ₂ -C ₆ alkenyl group, R ⁵ and R ⁶ together form a C ₁ -C ₆ alkylene group or an oxygen atom or a nitrogen atom, indicates which may be C ₁ -C ₆ alkylene group, the C ₁ -C ₆ alkylene group to form a ring which may be the same or different on the ring, C ₁ -C ₆ alkyl group, a carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, phenyl group, phenyl C ₁ -C ₆ alkyloxycarbonyl group or phenyl C ₁
It may also have one or more substituents selected from -C ₆ alkyl group. However except in the case of R ^1, R ^2, R ⁵ and R ⁶ are simultaneously hydrogen atoms, when showing the R ¹ is tert- butoxycarbonyl group and R ⁵ is benzyl group, R ⁶ except methyl group. ) Or the formula; embedded image NHCH (R ⁷ ) (CH ₂ ) nCOOR ⁸ (In the formula, R ⁷ is a hydrogen atom, a C ₁ -C ₆ alkyl group, cyclo C ₃
-C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁
-C ₆ alkyl group, amino C ₁ -C ₆ alkyl group, phenyl C ₁
-C ₆ alkyl group, or may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents selected from the group consisting of ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups and phenoxy groups on the ring. _1- C ₆ alkyl group, R ⁸
May be a hydrogen atom, a C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group, or the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C _1- C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Represents a substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, wherein n is 0 or 1
Indicates an integer. However, when R ¹ and R ² represent a hydrogen atom,
R ⁷ with the exception of methyl and iso- butyl group, R ¹ is benzyloxycarbonyl group, when an integer of R ⁷ is a hydrogen atom and n 0, R ⁸ excluding the ethyl group. ). ] The phenylalanine derivative represented by these, its optically active substance, its chemically acceptable salt, or its complex compound. 2. R ¹ represents a hydrogen atom or a C ₁ -C ₈ alkyl group, and R ² represents a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkyl. Carbonyl group, substituted C ₁ -C ₆ alkylcarbonyl group substituted by one or more halogen atoms which may be the same or different, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, Cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group,
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group,
May be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylcarbonyl group having a substituent on the ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenylsulfonyl group having 4 substituents on the ring,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group,
_{1 selected from a} C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 5 to 5 substituents on the ring, R ¹ and R ² together are a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom. It may also represent an interrupted C ₁ -C ₆ alkylene group or a phthaloyl group, wherein R ³ 'is of the formula; OR ⁴ ' (R ⁴ 'is hydrogen atom, C ₃ -C ₁₈ alkyl group, halo C ₁ -C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, cyclo C ₃ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C _1- C ₆ alkyl group, a carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, the same or different C ₁ -C ₆ may be alkyl One to two substituted amino C ₁ -C ₆ alkyl group having a substituent selected from the group, cyano C ₁ -C ₆ alkyl group, a phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano Group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenyl C ₂ -C ₆ alkenyl group having 1 to 5 substituents selected from the ring, phenoxy C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, phenylthio C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylthio C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, a phenylcarbonyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆
Substituted phenylcarbonyl C having 1 to 5 substituents on the ring selected from an alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _{A 1-} C ₆ alkyl group, a diphenyl C ₁ -C ₆ alkyl group, or an aromatic heterocycle which may be the same or different and has one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom on the ring. C ₁ -C
₆ Indicates an alkyl group. However, when R ¹ and R ² represent a hydrogen atom, R ⁴ excludes a hydrogen atom, a tert-butyl group and a benzyl group. ) The phenylalanine derivative according to claim 1, an optically active substance thereof, a chemically acceptable salt thereof, or a complex compound thereof. 3. A compound represented by the general formula (I):[Wherein, R¹Is a hydrogen atom or C₁-C₈ Represents an alkyl group,
R^TwoIs a hydrogen atom, C₁-C₈ Alkyl group, C₁-C₆Alkoxy
Carbonyl group, C₁-C₆Alkylcarbonyl group, the same or
Substitution substituted by one or more halogen atoms which may be different
C₁-C₆Alkylcarbonyl group, Phenyl C₁-C₆Alkyl
Groups, which may be the same or different, a halogen atom, nitro
Group, cyano group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl
Group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy group,
Ruboxyl group, C₁-C₆Alkoxycarbonyl group, C₁-C₆
Is it an alkylenedioxy group, a phenyl group or a phenoxy group?
Substituted 1 to 5 substituents selected from
Nil C₁-C₆Alkyl group, phenylcarbonyl group, same or
May be different, halogen atom, nitro group, cyano
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C₆
Alkoxy group, halo C₁-C ₆Alkoxy group, carboxyl
Group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Alkylene
Selected from dioxy, phenyl or phenoxy groups
Substituted phenylcarbo having 1 to 5 substituents on the ring
Nyl group, phenylsulfonyl group, same or different
, Halogen atom, nitro group, cyano group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group, carboxyl group, C₁-C₆Arco
Xycarbonyl group, C₁-C₆Alkylenedioxy group,
1-5 substitutions selected from nyl or phenoxy groups
A substituted phenylsulfonyl group having a group on the ring, phenyl
C₁-C₆Alkyloxycarbonyl group, the same or different
Also good, halogen atom, nitro group, cyano group, C₁-C₆A
Lucyl group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy
Group, halo C₁-C₆Alkoxy group, carboxyl group, C₁-C₆
Alkoxycarbonyl group, C₁-C₆Alkylenedioxy
1 to 5 selected from a group, a phenyl group or a phenoxy group
Substituted phenyl C having 4 substituents on the ring₁-C₆Alkyl
R represents an oxycarbonyl group¹And R^TwoTogether with each other
Become C₁-C₆Medium with alkylene group, oxygen atom or nitrogen atom
Refused C₁-C₆Indicates an alkylene group or a phthaloyl group
You can also. R^ThreeIs a formula; OR^Four (R^FourIs a hydrogen atom, C₁-C₁₈Alkyl group, halo C₁-C₈Al
Kill group, C_Two-C₆Alkenyl group, C_Two-C₆Alkynyl group,
Black C_Three-C₈Alkyl group, cyclo C_Three-C₈Alkyl C₁-C₆A
Rukyi group, hydroxy C₁-C₆Alkyl group, C₁-C₆Arco
Kiss C₁-C₆Alkyl group, C₁-C₆Alkoxy C₁-C₆Arco
Kiss C₁-C₆Alkyl group, C₁-C₆Alkylthio C₁-C₆Al
Kill group, carboxy C₁-C₆Alkyl group, C₁-C₆Alkoki
Sicarbonyl C₁-C₆Alkyl group, amino C₁-C₆Alkyl
Group, C which may be the same or different₁-C₆Select from alkyl groups
Substituted amino C having 1 to 2 substituents₁-C₆Al
Kill group, cyano C₁-C₆Alkyl group, phenyl group, same or
May be different, halogen atom, nitro group, cyano
Group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁-C ₆
Alkoxy group, halo C₁-C₆Alkoxy group, carboxyl
Group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Alkylene
Selected from dioxy, phenyl or phenoxy groups
A substituted phenyl group having 1 to 5 substituents on the ring,
Henil C₁-C₆Alkyl groups, which may be the same or different,
Rogen atom, nitro group, cyano group, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C
₆Alkoxy group, carboxyl group, C₁-C₆Alkoxyka
Rubonyl group, C₁-C₆Alkylenedioxy group, phenyl group
Alternatively, 1 to 5 substituents selected from a phenoxy group are substituted with a ring.
Substituted phenyl C having on₁-C₆Alkyl group, phenyl C_Two
-C₆Alkenyl groups, which may be the same or different, halogen
Atom, nitro group, cyano group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Al
Coxy group, carboxyl group, C₁-C₆Alkoxy Carboni
Group, C₁-C₆Alkylenedioxy group, phenyl group or fluorine
Having 1 to 5 substituents selected from the enoxy group on the ring
Substituted Phenyl C_Two-C₆Alkenyl group, phenoxy C₁-C
₆Alkyl groups, which may be the same or different, may be halogenated
Child, nitro group, cyano group, C₁-C₆Alkyl group, halo C₁-C
₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group, carboxyl group, C₁-C₆Alkoxycarbonyl
Group, C₁-C₆Alkylenedioxy group, phenyl group or phenyl group
Have 1-5 substituents on the ring selected from noxyl groups
Substituted phenoxy C₁-C₆Alkyl group, phenylthio C₁-C
₆Alkyl groups, which may be the same or different, may be halogenated
Child, nitro group, cyano group, C₁-C₆Alkyl group, halo C₁-C
₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆Arco
Xyl group, carboxyl group, C₁-C₆Alkoxycarbonyl
Group, C₁-C₆Alkylenedioxy group, phenyl group or phenyl group
Have 1-5 substituents on the ring selected from noxyl groups
Substituted Phenylthio C₁-C₆Alkyl group, phenylcarbo
Nil C₁-C₆Alkyl group, which may be the same or different, halo
Gen atom, nitro group, cyano group, C₁-C₆Alkyl group, ha
B c₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C₆
Alkoxy group, carboxyl group, C₁-C₆Alkoxycal
Bonyl group, C₁-C₆Alkylenedioxy group, phenyl group or
Is 1 to 5 substituents selected from phenoxy groups on the ring
Substituted Phenylcarbonyl C₁-C₆Alkyl group, di
Phenyl C₁-C₆Alkyl group or same or different
Well, selected from oxygen atom, sulfur atom or nitrogen atom
Aromatic heterocycle C having one or more heteroatoms on the ring₁-C₆
Shows an alkyl group. ), The formula; embedded image N (R^Five) -R⁶ (R^FiveIs a hydrogen atom, C₁-C₈Alkyl group, cyclo C_Three-C₈A
Lucyl group, C_Two-C₆Alkenyl group, C_Two-C₆An alkynyl group,
Cyano C₁-C₆Alkyl groups, which may be the same or different,
Rogen atom, nitro group, halo C₁-C₆Alkyl group, C₁-C₆
One or more units selected from an alkoxy group or a phenyl group
Cyano C having a substituent₁-C₆Alkyl group, C₁-C₆Alkoki
C₁-C₆Alcoroxy C₁-C₆Alkyl group, amino C₁-C
₆Alkyl group, which may be the same or different, C₁-C₆Alkyl
Substituted amino having 1-2 substituents selected from the group
C₁-C₆Alkyl group, phenyl group, same or different
, Halogen atom, nitro group, cyano group, C₁-C₆Archi
Le group, halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, ha
B c₁-C₆Alkoxy group, carboxyl group, C₁-C₆Arco
Xycarbonyl group, C₁-C₆Alkylenedioxy group,
1-5 substitutions selected from nyl or phenoxy groups
A substituted phenyl group having a group on the ring, phenyl C₁-C₆Al
Kill groups, which may be the same or different, a halogen atom, nit
B group, cyano group, C₁-C₆Alkyl group, halo C₁-C₆Archi
Group, C₁-C₆Alkoxy group, halo C₁-C₆An alkoxy group,
Carboxyl group, C₁-C₆Alkoxycarbonyl group, C₁-C
₆Alkylenedioxy group, phenyl group, phenoxy group
Substituted 1 to 5 substituents selected from
Nil C₁-C₆Alkyl group, phenoxy C₁-C₆Alkyl group,
May be the same or different, and may include a halogen atom, a nitro group,
Ano group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group, carboxy
Sil group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Archi
Select from dioxy group, phenyl group or phenoxy group
Substituted phenoxy having 1 to 5 substituents on the ring
C₁-C₆Alkyl group, phenyl C₁-C₆An alkyloxy group,
May be the same or different, and may include a halogen atom, a nitro group,
Ano group, C₁-C₆Alkyl group, halo C₁-C₆Alkyl group, C₁
-C₆Alkoxy group, halo C₁-C₆Alkoxy group, carboxy
Sil group, C₁-C₆Alkoxycarbonyl group, C₁-C₆Archi
Select from dioxy group, phenyl group or phenoxy group
Substituted phenyl C having 1 to 5 substituents on the ring₁
-C₆Alkyloxy group or guanidyl C₁-C₆Alkyl
Group, R⁶Is a hydrogen atom, C₁-C₆Alkyl group or C_Two
-C₆Represents an alkenyl group, R^FiveAnd R⁶Together with each other
C₁-C₆Alkylene group or oxygen atom or nitrogen atom
C, which may be suspended at₁-C₆An alkylene group,
C forming a ring₁-C₆Alkylene groups may be the same or different on the ring
Good, c₁-C₆Alkyl group, carboxyl group, C₁-C
₆Alkoxycarbonyl group, phenyl group, phenyl C₁-C
₆Alkyloxycarbonyl group or phenyl C₁-C₆Al
It has one or more substituents selected from a killoxy group.
Can also be. ) Or the formula; embedded image NHCH (R⁷) (CH_Two) NCOOR⁸ (Where R⁷Is a hydrogen atom, C₁-C₆Alkyl group, cyclo C_Three
-C₈Alkyl group, cyclo C_Three-C₈Alkyl C₁-C₆Alkyl
Group, C₁-C₆Alkoxy C₁-C₆Alkyl group, hydroxy C₁
-C₆Alkyl group, amino C₁-C₆Alkyl group, phenyl C₁
-C₆Alkyl groups, or they may be the same or different,
Rogen atom, nitro group, cyano group, C₁-C₆Alkyl group,
Halo C₁-C₆Alkyl group, C₁-C₆Alkoxy group, halo C₁-C
₆Alkoxy group, carboxyl group, C₁-C₆Alkoxyka
Rubonyl group, C₁-C₆Alkylenedioxy group, phenyl group
Alternatively, 1 to 5 substituents selected from a phenoxy group are substituted with a ring.
Substituted phenyl C having on₁-C₆Represents an alkyl group;⁸
Is a hydrogen atom, C₁-C₆Alkyl group, phenyl C₁-C₆Archi
Group or the same or different, a halogen atom,
Nitro group, cyano group, C₁-C₆Alkyl group, halo C₁-C₆A
Lucyl group, C₁-C₆Alkoxy group, halo C₁-C₆Alkoxy
Group, carboxyl group, C₁-C₆An alkoxycarbonyl group,
C₁-C₆Alkylenedioxy group, phenyl group or phenoxy
A group having 1 to 5 substituents selected from the group
Converted phenyl C₁-C₆Represents an alkyl group, n is 0 or 1
Indicates a number. ), X is a halogen atom, a nitro group,
Ano group, hydroxyl group, amino group, C₁-C₆Alkyl group, halo C₁
-C₆Alkyl group or C₁-C₆Represents an alkoxy group, m is
Indicates an integer of 1 to 2. ] Phenylalanine induction represented by
Conductor, its optically active substance, its chemically acceptable salt, or
Characterized by containing the complex compound as an active ingredient
Fruit tree gardening fungicide. 4. R ¹ represents a hydrogen atom or a C ₁ -C ₈ alkyl group, and R ² represents a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkyl group. Carbonyl group, substituted C ₁ -C ₆ alkylcarbonyl group substituted by one or more halogen atoms which may be the same or different, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, Cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group,
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group,
May be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylcarbonyl group having a substituent on the ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenylsulfonyl group having 4 substituents on the ring,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group,
_{1 selected from a} C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 5 to 5 substituents on the ring, R ¹ and R ² together are a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom. interrupted C ₁ -C ₆ alkylene group, or to signify an phthaloyl group, R ³ has the formula: ## STR6 ## oR ⁴ (R ⁴ is a hydrogen atom, C ₁ -C ₁₈ alkyl group, halo C ₁ - C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, cyclo C ₃ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, the same or different and good C ₁ -C ₆ alkyl Substituted amino C ₁ -C ₆ alkyl group having one to two substituents selected from, cyano C ₁ -C ₆ alkyl group, a phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenyl C ₂ -C ₆ alkenyl group having 1 to 5 substituents selected from the ring, phenoxy C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, phenylthio C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylthio C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, a phenylcarbonyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆
Substituted phenylcarbonyl C having 1 to 5 substituents on the ring selected from an alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _{A 1-} C ₆ alkyl group, a diphenyl C ₁ -C ₆ alkyl group, or an aromatic heterocycle which may be the same or different and has one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom on the ring. C ₁ -C
₆ Indicates an alkyl group. X is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group or a C ₁ -C ₆ alkoxy group, and m is 1 The fungicide for fruit and gardening according to claim 3, which is an integer of 2 to 5. 5. R ¹ represents a hydrogen atom or a C ₁ -C ₈ alkyl group, R ² represents a hydrogen atom or a C ₁ -C ₈ alkyl group, and R
³ is a formula; OR ⁴ (R ⁴ 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,
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkyl group, or may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Represents a substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from the ring. ),
X is a halogen atom, m is an integer of 1-2, The fungicide for fruit and gardening according to claim 4. 6. A fungicide for fruit gardening according to any one of claims 3 to 5 for controlling disease of fruit gardening crops.
A method for using a plant disease controlling agent, which comprises treating an effective amount thereof. 7. A compound represented by the general formula (I): [In the formula, R ¹ represents 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, a C ₁ -C ₆ alkylcarbonyl group, or a substituent substituted with one or more halogen atoms which may be the same or different.
C ₁ -C ₆ alkylcarbonyl group, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group , C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from an alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group, which may be the same or different, a halogen atom, Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenylcarbonyl group having a ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C _1- 1 to 5 C ₆ alkoxy groups, halo C ₁ -C ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups or phenoxy groups Substituted phenylsulfonyl group having a substituent on the ring, phenyl
C ₁ -C ₆ alkyloxycarbonyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group , Halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 4 substituents on the ring, R ¹ and R ² together are interrupted by a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom. It may also be a C ₁ -C ₆ alkylene group or a phthaloyl group. R ³ is of 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 C ₂ -C ₆ alkynyl group , Cyclo C ₃ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, the same or may be different C ₁ -C ₆ substituted amino C ₁ -C ₆ alkyl group having one to two substituents selected from alkyl groups , Cyano C ₁ -C ₆ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenyl C ₂ -C ₆ alkenyl group having 1 to 5 substituents selected from the ring, phenoxy C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, phenylthio C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylthio C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, a phenylcarbonyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆
Substituted phenylcarbonyl C having 1 to 5 substituents on the ring selected from an alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, diphenyl C ₁ -C ₆ alkyl group or aromatic heterocycle C which may be the same or different and has at least one hetero atom selected from oxygen atom, sulfur atom or nitrogen atom on the ring ₁ -C ₆
Shows an alkyl group. ), The formula; N (R ⁵ ) -R ⁶ (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, C ₂ -C ₆ alkynyl group,
Cyano C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆
A cyano C ₁ -C ₆ alkyl group having one or more substituents selected from an alkoxy group or a phenyl group, a C ₁ -C ₆ alkoxy C ₁ -C ₆ alcoroxy C ₁ -C ₆ alkyl group, an amino C _1- C
₆ alkyl group, a substituted amino having 1 to 2 substituents be the same or different are selected from a good C ₁ -C ₆ alkyl group
C ₁ -C ₆ alkyl group, phenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy ₁ to 5 substituents selected from a group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. Substituted phenyl group having a ring, phenyl C ₁ -C ₆ alkyl group, may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group,
Carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C
₆ alkylenedioxy group, phenyl group, substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from phenoxy group on the ring, phenoxy C ₁ -C ₆ alkyl group,
May be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted Phenoxy Having a Substituent on the Ring
C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkyloxy group,
May be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenyl C ₁ having the substituent of
-C ₆ alkyloxy group or guanidyl C ₁ -C ₆ alkyl group, R ⁶ is a hydrogen atom, C ₁ -C ₆ alkyl group or C ₂
-C ₆ an alkenyl group, R ⁵ and R ⁶ are C ₁ -C ₆ an alkylene group or an oxygen atom or a nitrogen which may be interrupted by atoms C ₁ -C ₆ alkylene group together with each other, the The C ₁ -C ₆ alkylene group forming a ring may be the same or different on the ring, and may be a C ₁ -C ₆ alkyl group, a carboxyl group, C ₁ -C
₆ Alkoxycarbonyl group, phenyl group, phenyl C ₁ -C
₆ alkyloxycarbonyl group or may have one or more substituents selected from phenyl C ₁ -C ₆ alkyl group. ) Or the formula; NHCH (R ⁷ ) (CH ₂ ) nCOOR ⁸ (In the formula, R ⁷ is a hydrogen atom, a C ₁ -C ₆ alkyl group, cyclo C ₃
-C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, hydroxy C ₁
-C ₆ alkyl group, amino C ₁ -C ₆ alkyl group, phenyl C ₁
-C ₆ alkyl group, or may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents selected from the group consisting of ₆ alkoxy groups, carboxyl groups, C ₁ -C ₆ alkoxycarbonyl groups, C ₁ -C ₆ alkylenedioxy groups, phenyl groups and phenoxy groups on the ring. _1- C ₆ alkyl group, R ⁸
Is a hydrogen atom, a C ₁ -C ₆ alkyl group, a phenyl C ₁ -C ₆ alkyl group or the same or different, a halogen atom,
Nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl Base,
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group on the ring, n is an integer of 0 or 1 Indicates. X is a halogen atom, nitro group, cyano group, hydroxyl group, amino group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, or a C ₁ -C ₆ alkoxy group, m is an integer of 1-2. ] The medical antifungal agent characterized by containing the phenylalanine derivative represented by these, its optically active substance, its chemically acceptable salt, or its complex compound as an active ingredient. 8. R ¹ represents a hydrogen atom or a C ₁ -C ₈ alkyl group, and R ² represents a hydrogen atom, a C ₁ -C ₈ alkyl group, a C ₁ -C ₆ alkoxycarbonyl group, or a C ₁ -C ₆ alkyl. Carbonyl group, substituted C ₁ -C ₆ alkylcarbonyl group substituted by one or more halogen atoms which may be the same or different, phenyl C ₁ -C ₆ alkyl group, which may be the same or different, halogen atom, nitro group, Cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group,
A substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group on the ring, a phenylcarbonyl group,
May be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C _1
1 to 5 selected from -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylcarbonyl group having a substituent on the ring, a phenylsulfonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C _6
1 to 5 selected from alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group
A substituted phenylsulfonyl group having 4 substituents on the ring,
Phenyl C ₁ -C ₆ alkyloxycarbonyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group,
C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group,
_{1 selected from a} C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group
A substituted phenyl C ₁ -C ₆ alkyloxycarbonyl group having 5 to 5 substituents on the ring, R ¹ and R ² together are a C ₁ -C ₆ alkylene group, an oxygen atom or a nitrogen atom. It may also represent an interrupted C ₁ -C ₆ alkylene group or a phthaloyl group, wherein R ³ is of the formula; OR ⁴ (R ⁴ is hydrogen atom, C ₁ -C ₁₈ alkyl group, halo C _1- C ₈ alkyl group, C ₂ -C ₆ alkenyl group, C ₂ -C ₆ alkynyl group, cyclo C ₃ -C ₈ alkyl group, cyclo C ₃ -C ₈ alkyl C ₁ -C ₆ alkyl group, hydroxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkylthio C ₁ -C ₆ alkyl group, carboxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxycarbonyl C ₁ -C ₆ alkyl group, an amino C ₁ -C ₆ alkyl group, the same or different and good C ₁ -C ₆ alkyl Substituted amino C ₁ -C ₆ alkyl group having one to two substituents selected from, cyano C ₁ -C ₆ alkyl group, a phenyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group , C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C _6
1 to 5 substituents selected from an alkoxy group, a halo C ₁ -C ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. A substituted phenyl group having a ring, a phenyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, a C ₁ -C ₆ alkyl group,
Halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C
Substituted phenyl C having 1 to 5 substituents on the ring selected from a ₆ alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _1- C ₆ alkyl group, phenyl C ₂
-C ₆ alkenyl group, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenyl C ₂ -C ₆ alkenyl group having 1 to 5 substituents selected from the ring, phenoxy C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Substituted phenoxy C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, phenylthio C ₁ -C
₆ alkyl groups, which may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C
₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group A substituted phenylthio C ₁ -C ₆ alkyl group having 1 to 5 substituents on the ring, a phenylcarbonyl C ₁ -C ₆ alkyl group, which may be the same or different, a halogen atom, a nitro group, a cyano group, C ₁ -C ₆ alkyl group, halo C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆
Substituted phenylcarbonyl C having 1 to 5 substituents on the ring selected from an alkoxy group, a carboxyl group, a C ₁ -C ₆ alkoxycarbonyl group, a C ₁ -C ₆ alkylenedioxy group, a phenyl group or a phenoxy group. _{A 1-} C ₆ alkyl group, a diphenyl C ₁ -C ₆ alkyl group, or an aromatic heterocycle which may be the same or different and has one or more heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom on the ring. C ₁ -C
₆ Indicates an alkyl group. X is a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, a C ₁ -C ₆ alkyl group, a halo C ₁ -C ₆ alkyl group or a C ₁ -C ₆ alkoxy group, and m is 1 The medical antifungal agent according to claim 7, which represents an integer of ˜2. 9. R ¹ represents a hydrogen atom or a C ₁ -C ₈ alkyl group, R ² represents a hydrogen atom or a C ₁ -C ₈ alkyl group, and R
³ is a formula; OR ⁴ (R ⁴ 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,
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, C ₁ -C ₆ alkoxy
C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group, phenyl C ₁ -C ₆ alkyl group, or may be the same or different, halogen atom, nitro group, cyano group, C ₁ -C ₆ alkyl group, halo C ₁
-C ₆ alkyl group, C ₁ -C ₆ alkoxy group, halo C ₁ -C ₆ alkoxy group, carboxyl group, C ₁ -C ₆ alkoxycarbonyl group, C ₁ -C ₆ alkylenedioxy group, phenyl group or phenoxy group Represents a substituted phenyl C ₁ -C ₆ alkyl group having 1 to 5 substituents selected from the ring. ),
The medical antifungal agent according to claim 8, wherein X represents a halogen atom and m represents an integer of 1 to 2.