JPH0717930A - Benzylhydrazone derivative and production thereof and fungicide for agriculture and horticulture - Google Patents

Abstract

PURPOSE:To obtain a novel benzylhydrazone derivative capable of exhibiting excellent control effect on blast of rice, downy mildew of cucumber, powdery mildew of barley, etc., at a low dose. CONSTITUTION:A compound of formula I [X is formula IV, formula V (R<5> is alkyl); Y is alkoxy, alkylthio, amino, etc.; Z is halogen or (halo)alkyl; (m) is 0-4; R<1> is H or (halo)alkyl; R<2> is formyl, alkylcarbonyl, alkylsulfonyl, aminocarbonyl, phenylcarbonyl, phenoxycarbonyl, etc.; R<3> and R<4> are H, CN, alkyl, cycloalkyl, alkoxy, alkylthio, alkylsulfynyl, alkylsulfonyl, phenyl, morpholino, or R<3> and R<4> together form alkylene or alkenylene], e.g. methyl 2-[2-[l-acetyl-2-[1-(3-chlorophenyl)ethylidene]hydrozinomethyl]phenyl]-2- methoxypropenoate. The compound is obtained by reacting a compound of formula II with a compound of formula III in the presence of a base or silver compound in an inert solvent.

Description

Detailed Description of the Invention

[0001]

The present invention relates to the general formula (I)

[Chemical 21]

[Wherein X is

Embedded image CH to OR ⁵ (in the formula, R ⁵ represents a (C _1-6 ) alkyl group), or

Embedded image N to OR ⁵ (wherein R ⁵ is the same as defined above).

Y may be a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, an amino group or the same or different (C
_1-6 ) represents a mono- or di-substituted amino group substituted with an alkyl group. Z may be the same or different and represents a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group, and m represents an integer of 0-4. R ¹ represents a hydrogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group.

R ² is a formyl group: (C _1-6 ) alkylcarbonyl group: halo (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylsulfonyl group: halo (C _1-6 ) alkylsulfonyl group : Aminocarbonyl group: mono- or di-substituted aminocarbonyl group, which may be the same or different, and has a substituent selected from formyl group or (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonyl group: (C _1-6 ) alkoxycarbonyl (C _1-6 ).
Alkylcarbonyl group: cyano (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylthiocarbonyl group: phenylcarbonyl group: may be the same or different, halogen atom, (C
_1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group
Phenylcarbonyl group having 5 substituents: phenyl
(C _1-6 ) alkylcarbonyl group: may be the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo ( A phenyl (C _1-6 ) alkylcarbonyl group having 1 to 5 substituents selected from C _1-6 ) alkoxy groups on the phenyl ring: a phenoxycarbonyl group: the same or different, a halogen atom, ( C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ).
Phenoxycarbonyl group having 1 to 5 substituents selected from an alkoxy group or a halo (C _1-6 ) alkoxy group on the phenyl ring: benzyloxycarbonyl group: may be the same or different, a halogen atom, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group or halo (C 1
_1-6 ) benzyloxycarbonyl group having 1 to 5 substituents selected from alkoxy groups on the phenyl ring: or di (C _1-6 ) substituted by the same or different (C _1-6 ) alkyl group _1-6 ) represents an alkylphosphonyl group.

R ³ and R ⁴ may be the same or different, and hydrogen atom: cyano group: (C _1-6 ) alkyl group: halo (C _1-6 ) alkyl group: (C _3-6 ) cycloalkyl group : Cyano (C _1-6 ) alkyl group: (C _2-6 ) alkenyl group: (C _3-6 ) cycloalkenyl group:
(C _1-6 ) alkoxy group: halo (C _1-6 ) alkoxy group: (C _1-6 )
_Alkylthio group: halo (C _1-6 ) alkylthio group: (C _1-6 ) alkylsulfinyl group: (C _1-6 ) alkylsulfonyl group:
(C _2-6 ) alkenylthio group: (C _2-6 ) alkynylthio group: (C
_1-6 ) alkoxy (C _1-6 ) alkyl group: (C _1-6 ) alkoxy (C
_1-6 ) alkylthio group: (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkylsulfonyl (C _1-6 ) alkyl group: (C
_3-6 ) Cycloalkylthio group: (C _1-6 ) alkoxycarbonyl (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonylthio group: phenyl group: same or different Also good, halogen atom, cyano group, nitro group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group,
Halo (C _1-6 ) alkylthio group, (C _1-6 ) alkylsulfinyl group, (C _1-6 ) alkylsulfonyl group,

Aminocarbonyl group, which may be the same or different, and is a mono- or di-substituted aminocarbonyl group selected from a (C _1-6 ) alkyl group or a (C _1-6 ) alkylcarbonyl group,
Cyano (C _1-6 ) alkoxy group, (C _1-6 ) alkoxycarbonyloxy group, amino group, may be the same or different, formyl group, (C _1-6 ) alkyl group or (C _1-6 ) alkyl Selected from a mono- or di-substituted amino group having a substituent selected from a carbonyl group, a (C _1-6 ) alkoxycarbonyl group, an aminocarbonyloxy group, and the same or different (C _1-6 ) alkyl group A mono- or di-substituted aminocarbonyloxy group having a substituent, a methylenedioxy group, a phenyl group,
May be the same or different, a phenyl group having 1 to 5 substituents selected from a halogen atom, a (C _1-6 ) alkyl group or a (C _1-6 ) alkoxy group, a phenoxy group, the same or different Also, halogen atom, cyano group, nitro group, (C
_1-6 ) alkyl group or phenoxy group having 1 to 5 substituents selected from halo (C _1-6 ) alkyl group, phenyl (C
_1-6 ) alkyl group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C
_1-6 ) Phenyl (C _1-6 ) alkyl groups having 1 to 5 substituents selected from alkyl groups on the phenyl ring, phenyl
(C _1-6 ) alkyloxy group, which may be the same or different, selected from a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. A phenyl (C _1-6 ) alkyloxy group having 5 substituents on the phenyl ring, a morpholino group, and one or more may be the same or different.
A morpholino group substituted by a (C _1-6 ) alkyl group, a pyrimidinyloxy group, and one or more same or different (C
_1-6 ) a pyrimidinyloxy group substituted with an alkyl group, a morpholinocarbonyl group, one or more morpholinocarbonyl groups substituted with one or more (C _1-6 ) alkyl groups, or adjacent carbon atoms Combined (C
_3-4 ) Phenyl group having 1 to 5 substituents selected from alkylene group: phenyl (C _1-6 ) alkylthio group: may be the same or different, (C _1-6 ) alkyl group or halo ( C _1-6 )
Phenyl (C _1-6 ) alkylthio group having 1 to 5 substituents selected from alkyl group on phenyl ring: phenylsulfonyl group: may be the same or different, (C _1-6 ) alkyl group or halo (C _1-6) phenylsulfonyl group having 1 to 5 substituents selected from alkyl groups on the phenyl ring: phenylsulfonyl (C _1-6) alkyl group: may be the same or different, (C _{1 -6} ) alkyl group or (C _1-6 ) haloalkyl group having 1 to 5 substituents on the phenyl ring, phenylsulfonyl (C _1-6 ) alkyl group: phenylthio (C 1-6) alkyl group : May be the same or different, (C
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, phenylthio (C _1-6 ) alkyl group: phenyl (C _1-6 ). Alkylthio (C
_1-6 ) Alkyl group: may be the same or different, and is 1 to 5 selected from a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group.
Phenyl (C _1-6 ) alkylthio (C _1-6 ) alkyl group having 4 substituents on the phenyl ring: amino (C _1-6 ) alkyl group:
They may be the same or different, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkylcarbonyl group, phenylcarbonyl group, which may be the same or different, and are selected from (C _1-6 ) alkyl group or halo (C _1-6 ) alkyl group. 1-5
Mono- or di-substituted amino (C _1-6 ) alkyl group selected from a phenylcarbonyl group having 4 substituents on the phenyl ring, a phenyl group, or a benzyl group: furfurylthio group:
Furfurylthio (C _1-6 ) alkyl group: Morpholino (C _1-6 ) alkyl group: or 1 or more same or different (C _1-6 ).
Morpholino (C _1-6 ) alkyl group substituted by an alkyl group:

[0007]

Embedded image wherein —CO—R ⁶ (wherein R ⁶ is a (C _1-6 ) alkyl group; a halo (C _1-6 ) alkyl group; a (C _1-6 ) alkoxy group; a halo (C _1-6). ) Alkoxy group; (C
_1-6 ) alkylthio group; halo (C _1-6 ) alkylthio group; amino group; may be the same or different and selected from (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group or phenyl group A mono- or di-substituted amino group having a substituted group; a phenyl group; which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group , (C _1-6 ).
Alkoxy group, halo (C _1-6 ) alkoxy group, amino group, the same or different, and having a substituent selected from (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Or a di-substituted amino group, a phenyl group, the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ).
A phenyl group having 1 to 5 substituents selected from alkyl groups, a phenoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _{1 -6} ) A phenoxy group having 1 to 5 substituents selected from an alkyl group, a benzyl group, a benzyloxy group, which may be the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) 1 to 3 selected from alkyl groups
Benzyloxy group having 5 substituents on the phenyl ring, pyridyloxy group, may be the same or different and is selected from halogen atom, (C _1-6 ) alkyl group or halo (C _1-6 ) alkyl group. A pyridyloxy group having 1 to 4 substituents,

1 to 1 selected from a methylenedioxy group or a (C _3-4 ) alkylene group bonded to an adjacent carbon atom.
A phenyl group having 5 substituents; a benzyloxy group;
May be the same or different, halogen atom, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or halo
A benzyloxy group having 1 to 5 substituents on the phenyl ring selected from (C _1-6 ) alkylthio groups; or the same or different, 1 to 3 oxygen atoms, sulfur atoms or nitrogen atoms Having a heteroatom selected from (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, and (C
5-6 membered heterocyclic group which may have a substituent selected from _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group is shown. ):

Amino group: may be the same or different, (C
_1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, (C _1-6 ) alkoxy (C _1-6 ).
Alkyl group, di (C _1-6 ) alkoxy (C _1-6 ) alkyl group, amino (C _1-6 ) alkyl group, may be the same or different (C _1-6 ).
Mono or di (C _1-6 ) alkylamino substituted with an alkyl group (C _1-6 ) alkyl group, phenyl group, which may be the same or different, a halogen atom, (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or phenyl group having 1 to 5 substituents selected from halo (C _1-6 ) alkyl group, pyridyl (C _1-6 ) alkyl group Or morpholino (C _1-6 ).
Mono- or di-substituted amino group having a substituent selected from an alkyl group: phenyl (C _1-6 ) alkyl group: may be the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or 1 to halo (C _1-6 ) alkylthio group selected from Phenyl (C _1-6 ) alkyl group having 5 substituents on the phenyl ring: phenyl (C _2-6 ).
Alkenyl group: phenyl (which may be the same or different and has 1 to 5 substituents selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group on the phenyl ring. C _2-6 ) alkenyl group: naphthyl group: 5-7 membered heterocyclic group having 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom, which may be the same or different: or said 5 7-membered heterocyclic group and benzene ring or (C4-
6) represents a heterocyclic group in which a cycloalkane ring is condensed, and these heterocyclic groups may be the same or different, a halogen atom,
Cyano group, nitro group, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ). 1-5 selected from alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) alkoxycarbonyl group, phenyl group and halogen atoms which may be the same or different.
Selected from a phenyl group having 1 substituent, a benzyl group, a pyridyl group, a pyrimidyl group or a dioxolane group.
It can also have one or more substituents.

R ³ and R ⁴ together may be interrupted by an oxygen atom, a sulfur atom, a nitrogen atom, a carbonyl group, or a nitrogen atom substituted by a (C _1-6 ) alkyl group or a phenyl group. Good (C _1-6 ) alkylene group or (C _2-6 ) represents an alkenylene group, the alkylene group or alkenylene group may be the same or different on the alkylene chain or the alkenylene chain, (C _1-6 ) alkyl Group, halo (C _1-6 ) alkyl group,
It may have one or more substituents selected from a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group, and can be condensed with a benzene ring to form a condensed ring group. . ] The present invention relates to a benzylhydrazone derivative represented by the following, a method for producing the same, and an agricultural and horticultural fungicide.

[0011]

2. Description of the Related Art JP-A-4-288045 and 4-
No. 261147, No. 4-182461, No. 3
No. 169842, No. 3-120246, W
O93 / 15046 and the like disclose compounds such as acrylic acid esters or amides and N-phenylcarbamic acid, and describe that they are useful as agricultural and horticultural germicides.

[0012]

DISCLOSURE OF INVENTION Problems to be Solved by the Invention As a result of intensive studies by the present inventors to provide a more useful fungicide for agricultural and horticultural use, a benzylhydrazone derivative represented by the general formula (I) has not been reported in the literature. The present invention has been completed by discovering that it is a novel compound described above and has an excellent bactericidal effect at a low dose.

[0013]

As a definition of each substituent represented by the general formula (I) of the present invention, a halogen atom means a halogen atom such as a chlorine atom, a fluorine atom, a bromine atom or an iodine atom, For example, each substituent is (C _1-6 ) alkyl is methyl,
1 carbon atom such as ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl
It indicates 6 alkyl groups, (C _1-6) methoxy alkoxy, ethoxy, n- propoxy, i- propoxy, n- butoxy, i- butoxy, s- butoxy, t-butoxy, n- pentyloxy, n-hexyloxy or the like is an alkoxy group having 1 to 6 carbon atoms, and (C _1-6 ) alkylthio is methylthio,
Ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio,
n-pentylthio, n-hexylthio, etc., having 1 to 6 carbon atoms
Represents an alkylthio group of halo, which may be the same or different from halo, and represents a group substituted with one or more halogen atoms,
For example, a halo (C _1-6 ) alkyl group, which may be the same as or different from one or more halogen atoms and has 1 to 6 carbon atoms.
Is an alkyl group.

The benzylhydrazone derivative represented by the general formula (I) of the present invention can be produced, for example, by the method shown below. Manufacturing method 1.

[Chemical 25] [In the formula, R ¹ , R ² , R ³ , R ⁴ , X, Y, Z and m are the same as defined above. Hal represents a halogen atom. ] The compound represented by the general formula (II) is represented by reacting the compound represented by the general formula (II) with the compound represented by the general formula (III) in the presence of a base or a silver compound and an inert solvent. Benzylhydrazone derivatives can be prepared.

The inert solvent which can be used in this reaction may be any inert solvent which does not markedly hinder the progress of this reaction, for example, methanol, ethanol or isopropanol.
, Tert-butanol, alcohols such as diethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme and diglyme. , Dichloroethane,
It is possible to use halogenated hydrocarbons such as chloroform, carbon tetrachloride and tetrachloroethane, aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene and toluene, nitriles such as acetonitrile, dimethylformamide, dimethylsulfoxide and water. These inert solvents can be used alone or in a mixture.

The two-phase reaction can be carried out using water and a water-insoluble inert solvent, in which case a phase transfer catalyst such as triethylbenzylammonium chloride or trioctylmethylammonium chloride can be used.
As the base used in this reaction, an inorganic base or an organic base can be used. For example, as the inorganic base, sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogen carbonate, sodium hydroxide, potassium hydroxide, calcium hydroxide, etc. Carbonates or hydroxides of alkali metal atoms or alkaline earth metal atoms, hydrides of alkali metal atoms such as lithium hydride and sodium hydride can be used, and as the organic base, for example, sodium methoxide, Alkoxides of alkali metal atoms such as potassium tert-butoxide, diethylamine, triethylamine, pyridine, benzyltrimethylammonium hydroxide, etc. can be used, and these bases can be used alone or in a mixture. The amount is in the general formula (II) It may be appropriately selected from the range of equimolar to excess molar with respect to the represented compound.

As the silver compound which can be used in this reaction, for example, silver oxide can be used, and the amount thereof is appropriately selected from the range of equimolar to excess molar to the compound represented by the general formula (II). You can select and use it. Since this reaction is an equimolar reaction, the compound represented by the general formula (II) and the general formula
The compound represented by (III) may be used in an equimolar amount, but any one of the reactants may be used in excess. The reaction temperature may be selected from -70 ° C to the boiling point range of the inert solvent used, but is preferably in the range of -40 ° C to room temperature.
The reaction time is not constant depending on the reaction temperature, the reaction scale, etc., but generally it may be selected from the range of 30 minutes to 48 hours. After completion of the reaction, the desired product can be isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization or the like to produce a benzylhydrazone derivative represented by the general formula (I). .

Manufacturing method 2.

[Chemical formula 26] [In the formula, R ¹ , R ² , R ³ , R ⁴ , Y ¹ , Y ² , X, Z and m are the same as defined above. ]

By reacting the benzylhydrazone derivative represented by the general formula (I ') with the amine represented by the general formula (IV) in the presence of an inert solvent, the compound represented by the general formula (I'') can be obtained. Benzylhydrazone derivatives can be prepared.

The inert solvent which can be used in this reaction may be any inert solvent which does not markedly hinder the progress of this reaction, for example, methanol, ethanol or isopropanol.
, Tert-butanol, alcohols such as diethylene glycol, halogenated aliphatic hydrocarbons such as dichloromethane, chloroform and carbon tetrachloride, aromatic hydrocarbons such as benzene, toluene and xylene, methyl cellosolve , Ethers such as diethyl ether, diglyme, dioxane and tetrahydrofuran, dimethylformamide, dimethylsulfoxide, water and the like can be used, and these inert solvents can be used alone or in a mixture. Since this reaction is an equimolar reaction, the benzylhydrazone derivative represented by the general formula (I ') and the general formula
The amines represented by (IV) may be used in equimolar amounts, but it is preferable to use the amines represented by the general formula (IV) in excess.

The reaction temperature may be selected from -70 ° C to the boiling point range of the inert solvent used, preferably -20 ° C.
~ Room temperature range. The reaction time depends on the reaction temperature and the reaction scale.
Although it does not vary depending on factors such as the schedule, it may be selected from the range of 30 minutes to 48 hours. After completion of the reaction, the target compound is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization, etc.
A benzylhydrazone derivative represented by (I ″) can be produced.

The representative compounds of the benzylhydrazone derivative represented by the general formula (I) are shown below, but the present invention is not limited thereto. General formula (I)

[Chemical 27]

[0023]

[Table 1]

[0024]

[Table 2]

[0025]

[Table 3]

[0026]

[Table 4]

[0027]

[Table 5]

[0028]

[Table 6]

[0029]

[Table 7] Table 1 (continued)

[0030]

[Table 8] Table 1 (continued)

[0031]

[Table 9] Table 1 (continued)

[0032]

[Table 10] Table 1 (continued)

[0033]

[Table 11] Table 1 (continued)

[0034]

[Table 12] Table 1 (continued)

[0035]

[Table 13] Table 1 (continued)

[0036]

[Table 14] Physical properties of the compounds in Table 1 are shown in Table 2.

[0037]

[Table 15]

[0038]

[Table 16]

[0039]

[Table 17]

[0040]

[Table 18]

[0041]

[Table 19]

[0042]

[Table 20]

[0043]

[Table 21]

[0044]

[Table 22]

[0045]

[Table 23]

[0046]

[Table 24]

[0047]

[Table 25]

[0048]

[Table 26]

[0049]

[Table 27]

[0050]

[Table 28]

[0051]

[Table 29]

[0052]

[Table 30]

[0053]

[Table 31]

The general formula which is a starting compound for producing the benzylhydrazone derivative represented by the general formula (I) of the present invention
The compounds represented by (II) are disclosed in JP-A-4-288045, JP-A-4-261147, JP-A-4-182461, JP-A-3-169842 and JP-A-312024.
It can be manufactured by the manufacturing method described in Japanese Patent No. 6 or the like. The compound represented by the general formula (III) is A. MAQU
ESTIAU, Tetrahedron, '87, 41
It can be produced by the method described in 85, etc. Typical examples of this reaction are shown below, but the present invention is not limited thereto.

[0055]

【Example】

Example 1 2- [2- [1-acetyl-2- [1-
Production of methyl (3-chlorophenyl) ethylidene] hydrazinomethyl] phenyl] -2-methoxypropenoate (Compound No 22)

[Chemical 28] 0.15 g of sodium hydride (3.7 mmol, purity 6)
2%) in 20 ml of dimethylformamide, 0.78 g (3.7 mmol) of 2- [1- (3-chlorophenyl) ethylidene] acetohydrazide, and the mixture is stirred at room temperature for 30 minutes, and then 2- Methyl (2-bromomethylphenyl) -3-methoxypropenoate 0.8
9 g (3.1 mmol) was added and the reaction was carried out for 3 hours with stirring. After completion of the reaction, the reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract solution was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product by column chromatography. -(Ethyl acetate: n-hexane = 1: 2) was used to purify the target compound by 0.73.
g was obtained. Physical properties Paste yield 57% ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 2.19 (3H, s), 2.33 (3H, s), 3.70 (3H, s), 3.83 (3H, s ), Five.
11 (2H, s), 7.16-7.55 (6H, m), 7.60 (1H, s), 7.71 (1H, d),
7.84 (1H, s).

Example 2 2- [2- [1-acetyl-
Preparation of methyl 2- [1- (4-methylphenyl) ethylidene] hydrazinomethyl] phenyl] -2-methoxyiminoacetate (Compound No 80)

[Chemical 29] 0.11 g (2.8 mmol, 6 purity) of sodium hydride
2%) in 20 ml of dimethylformamide, then 0.50 g (2.6 mmol) of 2- [1- (4-methylphenyl) ethylidene] acetohydrazide, and the mixture is stirred at room temperature for 30 minutes, then 2 Methyl-(2-bromomethylphenyl) -2-methoxyiminoacetate 1.0
g (2.8 mmol, purity 80%) was added and the reaction was carried out for 4 hours with stirring. After completion of the reaction, the reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract solution was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product by column chromatography. 0.30 g of the desired product was obtained by purification with-(ethyl acetate: n-hexane = 1: 2). Physical properties mp 97 ℃ Yield 29%

Example 3 N-methyl-2- [2- [1
-Acetyl-2- [1- (3,4-dimethoxyphenyl) ethylidene] hydrazinomethyl] phenyl] -3-
Production of methoxyiminoacetic acid amide (Compound No103)

[Chemical 30] Methyl 2- [2- [1-acetyl-2- [1- (3,4-dimethoxyphenyl) ethylidene] hydrazinomethyl] phenyl] -3-methoxyiminoacetate 0.30 g
(0.68 mmol) was dissolved in 30 ml of methanol, 2 ml of 40% aqueous solution of methylamine was added to the solution, and the reaction was carried out at room temperature for 2 hours. After completion of the reaction, methanol was distilled off under reduced pressure, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give 0.30 g of the desired product. Obtained. Physical properties Paste yield 100% ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 2.11 (3H, s), 2.26 (3H, s), 2.90 (3H, d), 3.91 (3H, s ), 3.
92 (3H, s), 3.96 (3H, s), 5.13 (2H, s), 6.75 (1H, br.q), 6.
85 (1H, d), 7.15-7.56 (7H, m).

Example 4 N-methyl-2- [2- [1
-Acetyl-2- [1- (4-phenyl-1-piperazinyl) ethylidene] hydrazinomethyl] phenyl] -3
-Production of methoxyiminoacetic acid amide (Compound No 164)

[Chemical 31] 2- [2- [1-acetyl-2- [1- (4-phenyl-1-piperazinyl) ethylidene] hydrazinomethyl]
Phenyl] -3-methoxyiminoacetate methyl ester 0.20 g
(0.42 mmol) was dissolved in 30 ml of methanol, 2 ml of 40% aqueous solution of methylamine was added to the solution, and the reaction was carried out at room temperature for 2 hours. After completion of the reaction, methanol was distilled off under reduced pressure, the desired product was extracted with ethyl acetate, the extract was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain 0.20 g of the desired product. Obtained. Physical properties mp129 ℃ Yield 100%

Example 5 2- [2- [1-acetyl-
2- (1-morpholinoethylidene) hydrazinomethyl]
Phenyl] -2-methoxyiminoacetate methyl production (Compound No 159)

[Chemical 32] 0.60 g (5.4 mmol) of potassium t-butoxide was added to 60 ml of dimethylformamide, and then 2- (1
-Morpholino ethylidene) acetylhydrazine 0.80
g (4.2 mmol) was added and the mixture was stirred at room temperature for 30 minutes, then cooled to 0 ° C. and methyl 2- (2-bromomethylphenyl) -2-methoxyiminoacetate 1.2 g.
(4.2 mmol) was added and the reaction was carried out with stirring for 3 hours. After completion of the reaction, the reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract solution was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product by column chromatography. By purifying with-(ethyl acetate: n-hexane = 1: 2), 0.66 g of the desired product was obtained. Physical property paste yield 40%. ¹ H-NMR (CDCl ₃ / TMS, δ value (ppm)) 2.03 (3H, s), 2.08 (3H, s), 3.36 (4H, t), 3.72 (4H, t), 3.
85 (3H, s), 4.02 (3H, s), 5.03 (2H, s), 7.18-7.50 (4H, m).

Example 6 2- [2- [1-acetyl-
Preparation of methyl 2- [1- (2,6-dimethylmorpholino) ethylidene] hydrazinomethyl] phenyl] -3-methoxyperopenoate (Compound No 161)

[Chemical 33] 0.90 g (7.9 mmol) of potassium t-butoxy was added to 60 ml of dimethylformamide, and then 2- [1
-(2,6-Dimethylmorpholino) ethylidene] -1-
Acetohydrazide (1.7 g, 7.9 mmol) was added, and the mixture was stirred at room temperature for 30 minutes, and then cooled to 0 ° C. to obtain 2
1.5 g (5.3 mmol) of methyl-(2-bromomethylphenyl) -3-methoxypropenoate was added and the reaction was carried out under stirring for 3 hours. After completion of the reaction, the reaction solution was poured into water, the target product was extracted with ethyl acetate, the extract solution was washed with water and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to obtain a crude product by column chromatography. By refining with-(ethyl acetate: n-hexane = 1: 2), 0.48 g of the desired product was obtained. Physical properties Paste yield 22% ¹ H-NMR [CDCl ₃ / TMS, δ value (ppm)] 1.19 (6H, d), 2.02 (3H, s), 2.05 (3H, s), 2.41 (2H, dd ), 3.
52-3.83 (4H, m), 3.65 (3H, s), 3.76 (3H, s), 5.02 (2H, s),
7.08-7.50 (4H, m), 7.53 (1H, s).

The benzylhydrazone derivative represented by the general formula (I) of the present invention is useful as an agricultural and horticultural fungicide,
For example, rice blast (Pyricularia oryzae), rice blight (Rhizoctonia solani), rice sesame leaf blight (Cochliobolus)
miyabeanus), barley and wheat powdery mildew (Erysip
graminis), powdery mildew on various host plants, oat crown rust (Puccinia coronata) and other plant rusts, tomato blight (Phytophthora infes).
tans) and other plant epidemics, cucumber downy mildew (Pseudo)
peronospora cubensis), downy mildew of grape (Plasmopara
downy mildew of various plants such as viticola), Botrytis cinerea of cucumber and other plants, apple scab (Venturia inaequalis), leaf spot of apple (Alterna)
ria mali), pear black spot (Alternaria kikuchiana), citrus black spot (Diaporthe citri), etc., and has a very high control effect.

The agricultural and horticultural fungicide of the present invention has a remarkable bactericidal effect against the above-mentioned diseases that damage paddy field crops, field crops, fruit trees, vegetables, other crops, flowers and the like. According to the expected timing of the occurrence of paddy fields, paddy fields, fields, fruit trees,
The intended effect of the agricultural / horticultural fungicide of the present invention can be obtained by treating vegetables, other crops, paddy water such as flowers, seeds, foliage or soil.

When the benzylhydrazone derivative represented by the general formula (I) of the present invention is used as a fungicide for agricultural and horticultural use, it is used by formulating it into a convenient shape according to a conventional method for agricultural chemicals. Is common. That is, the benzylhydrazone derivative represented by the general formula (I) of the present invention is dissolved, separated, suspended, by mixing these in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio. It may be mixed, impregnated, adsorbed or adhered, and then formulated into an appropriate dosage form, for example, a suspension, emulsion, liquid, wettable powder, granule, powder, tablet or the like for use. The inert carrier which can be used in the present invention may be either solid or liquid, and examples of the material which can be a solid carrier include soybean flour, cereal flour, wood flour, bark flour, sawdust powder and tobacco stem flour. , Walnut shell powder, bran,
Fiber powder, residue after extraction of plant extracts, synthetic polymers such as ground synthetic resin, clays (eg kaolin, bentonite, acid clay etc.), talcs (eg talc, pyrophyllide etc.), silicas (eg diatomaceous earth, silica sand) , Mica, white carbon [Synthetic high-dispersion silicic acid, also known as hydrous fine powder silicon and hydrous silicic acid, and some products contain calcium silicate as the main component.]), Activated carbon, sulfur powder, pumice stone, calcined diatomaceous earth, brick crushed Things, fly ash, sand,
Inorganic mineral powder such as calcium carbonate, calcium phosphate,
Examples thereof include chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and ammonium salt, and compost, which are used alone or in the form of a mixture of two or more kinds.

The material which can be used as a liquid carrier is selected from those having solvent ability itself, and those having no solvent ability but capable of dispersing the active ingredient compound with the aid of an auxiliary agent. The following carriers can be mentioned as typical examples, and these can be used alone or in the form of a mixture of two or more kinds, and for example, water, alcohols (for example, methanol, ethanol, isopropanol, butanol). -, Ethylene glycol, etc.), ketones (for example, acetone, methyl ethyl ketone, methyl isobutyl ketone,
Diisobutyl ketone, cyclohexanone, etc.), ethers (eg ethyl ether, dioxane, cellosolve,
Dipropyl ether, tetrahydrofuran etc.), aliphatic hydrocarbons (eg kerosene, mineral oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, alkylnaphthalene etc.), halogenated hydrocarbons (eg dichloroethane) , Chloroform, carbon tetrachloride, chlorinated benzene, etc.), esters (for example, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, etc.), amides (for example, dimethylformamide, diethylformamide, Examples thereof include dimethylacetamide and the like), nitriles (for example, acetonitrile and the like), dimethylsulfoxides and the like. Examples of other auxiliary agents include the representative auxiliary agents exemplified below. These auxiliary agents are used depending on the purpose, and may be used alone or, in some cases, in combination of two or more auxiliary agents, In some cases it is possible to use no adjuvant at all.

Surfactants are used for the purpose of emulsifying, dispersing, solubilizing and / or wetting the active ingredient compounds, for example polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxy. Ethylene higher fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monooleate, alkyl aryl sulfonate, naphthalene sulfonic acid condensate,
Examples thereof include surfactants such as lignin sulfonate and higher alcohol sulfate. In addition, for the purpose of stabilizing the dispersion of active ingredient compounds, adhering and / or binding, auxiliary agents exemplified below can be used, for example, casein, gelatin, starch, methyl cellulose, carboxymethyl cellulose. It is also possible to use auxiliary agents such as gum arabic, polyvinyl alcohol, pine oil, bran oil, bentonite and lignin sulfonate.

The following auxiliaries may be used for improving the fluidity of the solid product, for example waxes, stearates, alkyl phosphates and the like. As a deflocculant for a suspending product, an auxiliary agent such as a naphthalenesulfonic acid condensate or a condensed phosphate can be used. As the defoaming agent, for example, an auxiliary agent such as silicone oil may be used. The compounding ratio of the active ingredient compound can be adjusted as required. For example, 0.01 to 50% by weight in the case of powder or granules, and 0.01 to 50% in the case of emulsion or wettable powder. Weight percent is suitable.

The agricultural / horticultural fungicide containing the benzylhydrazone derivative represented by the general formula (I) of the present invention as an active ingredient is used as it is for the purpose of controlling various diseases, or is appropriately diluted or suspended with water or the like. In such a form, an effective amount for disease control may be applied to a crop where the occurrence of the disease is predicted or a place where the occurrence of the disease is not desirable and used. The amount of the agricultural / horticultural fungicide containing the benzylhydrazone derivative represented by the general formula (I) of the present invention as an active ingredient has various factors such as purpose, target disease, growing condition of crops, tendency of disease occurrence, Although it varies depending on the weather, environmental conditions, dosage form, application method, application site, application time, etc., it may be appropriately selected according to the purpose from the range of 0.1 g to 1 kg per 10 aal as the active ingredient compound.

Agricultural and horticultural fungicides containing the benzylhydrazone derivative represented by the general formula (I) of the present invention as an active ingredient are used for the purpose of further controlling the disease to be controlled, the appropriate control period, or reducing the dose. It is also possible to use it by mixing with other agricultural and horticultural fungicides. Typical formulation examples and test examples of the present invention are shown below, but the present invention is not limited thereto. In the prescription examples, “part” means “part by weight”.

Formulation Example 1 Compound of the present invention 50 parts Xylene 40 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 10 parts The above are uniformly mixed and dissolved to obtain an emulsion. Formulation Example 2 Compound of the present invention 3 parts Cray powder 82 parts Diatomaceous earth powder 15 parts The above are uniformly mixed and pulverized to give a powder.

Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts Calcium lignin sulfonate 5 parts The above components are uniformly mixed and kneaded by adding an appropriate amount of water to granulate,
Dry to make granules. Formulation Example 4 Compound of the present invention 20 parts 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.

Test Example 1 Control Test Against Powdery Mildew of Barley Powdery mildew fungus (Erys) was applied to barley (1 leaf stage) planted in a pot.
Spores of iphe graminis f. sp. hordei) are sprinkled and inoculated, and one day later, 200 p containing the compound of the present invention as an active ingredient
The chemical solution of pm was sprayed and left in a thermostatic chamber at 25 ° C. The lesion area was investigated one week after the inoculation, and the effect was judged by the following criteria in comparison with the untreated plot. A: Control value 100 to 95% B: Control value 94 to 80% C: Control value 79 to 60% D: Control value 59 to 0% The results are shown in Table 3.

Test Example 2 Control test against cucumber downy mildew A 200 ppm drug solution containing the compound of the present invention as an active ingredient was sprayed on potted cucumbers (two-leaf stage), and one day later, zoospores of downy mildew (Pseudoperonospora cubensis). The suspension was spray inoculated. After the inoculation, the leaves were left in a humid chamber at 25 ° C for 1 day and left in the greenhouse for 6 days to cause sufficient disease, and then the disease degree of each leaf was investigated in comparison with the untreated plot, and the effect was judged according to the same criteria as in Test Example 1. did. The results are shown in Table 3.

Test Example 3 Rice Blast Control Test by Spraying Potato rice (5-leaf stage) was thoroughly sprayed with 200 ppm of the drug solution containing the compound of the present invention as an active ingredient, and after air-drying, rice blast fungus (Pyricularia oryzae) The spore suspension was spray inoculated. After inoculation, leave it in a humid chamber at 20 ° C for 1 day and leave it in a greenhouse for 6 days to fully develop the disease, then investigate the number of lesions on each leaf,
The effect was judged based on the same criteria as in Test Example 1 in comparison with the untreated section. The results are shown in Table 3.

Test Example 4 Control test against late blight of tomato A potted tomato (four leaves stage) was sprayed with 200 ppm of a drug solution containing the compound of the present invention as an active ingredient, and one day later,
hytophthora infestans) sprayed with a zoospore suspension,
After being left in a humid chamber at 25 ° C. for 1 day and placed in a greenhouse for 6 days to cause sufficient disease, the degree of disease on each leaf was investigated, and the effect was judged based on the same criteria as in Test Example 1 in comparison with the untreated plot. The results are shown in Table 3.

Test Example 5 Control test against gray mold of cucumber (therapeutic effect) The cotyledon of a potted cucumber (1 leaf stage) was cut out and PS
A lawn of Botrytis cinerea cultivated on the A medium was inoculated and left under a humid chamber condition of 15 ° C. for 1 day, and then cotyledons were immersed in a 200 ppm drug solution containing the compound of the present invention as an active ingredient. .. Then, after leaving for 3 days under the condition of a humid chamber at 15 ° C. to cause sufficient disease, the lesion diameter was measured, and the effect was judged based on the same criteria as in Test Example 1 in comparison with the untreated group. The results are shown in Table 3.

[0076]

[Table 32]

[0077]

[Table 33]

[0078]

[Table 34]

[0079]

[Table 35]

[0080]

[Table 36]

[0081]

[Table 37]

[0082]

[Table 38]

[0083]

[Table 39]

[0084]

[Table 40]

[0085]

[Table 41]

Note: Eg barley powdery mildew Pc cucumber downy mildew Ps rice blast Pi tomato plague Bc cucumber gray mold

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Office reference number FI Technical indication location A01N 43/28 9155-4H 43/40 101 C 9155-4H N 9155-4H K 9155-4H 43 / 60 9155-4H 43/84 101 9155-4H 47/24 D 9155-4H 47/42 Z 9155-4H C07C 249/16 251/80 251/86 255/66 9357-4H 317/26 7419-4H 323/48 7419-4H 323/52 7419-4H C07D 207/20 207/335 211/14 213/54 213/89 237/10 239/26 8615-4C 241/12 241/50 295/12 AZ 307/52 311 / 58 317/58 333/10 333/28 339/06

Claims (10)

[Claims] 1. A compound represented by the general formula (I): [In the formula, X is CH 2 -OR ⁵ (in the formula, R ⁵ represents a (C _1-6 ) alkyl group), or N 3 -OR ⁵ (wherein R ⁵ is The same as the above). Y represents a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, an amino group or a mono- or di-substituted amino group substituted by the same or different (C _1-6 ) alkyl group. Z may be the same or different and may be a halogen atom, a (C _1-6 ) alkyl group or a halo (C 1
_1-6 ) alkyl group, and m represents an integer of 0-4. R ¹ represents a hydrogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. R ² is a formyl group: (C _1-6 ) alkylcarbonyl group: halo (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylsulfonyl group: halo (C _1-6 ) alkylsulfonyl group: aminocarbonyl Group: mono- or di-substituted aminocarbonyl group which may be the same or different and has a substituent selected from formyl group or (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonyl group: (C _{1 -6} ) Alkoxycarbonyl (C _1-6 ) alkylcarbonyl group: cyano (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylthiocarbonyl group: phenylcarbonyl group: may be the same or different, a halogen atom, (C
_1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group
Phenylcarbonyl group having 5 substituents: phenyl
(C _1-6 ) alkylcarbonyl group: may be the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo ( A phenyl (C _1-6 ) alkylcarbonyl group having 1 to 5 substituents selected from C _1-6 ) alkoxy groups on the phenyl ring: a phenoxycarbonyl group: the same or different, a halogen atom, ( C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ).
Phenoxycarbonyl group having 1 to 5 substituents selected from an alkoxy group or a halo (C _1-6 ) alkoxy group on the phenyl ring: benzyloxycarbonyl group: may be the same or different, a halogen atom, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group or halo (C 1
_1-6 ) a benzyloxycarbonyl group having 1 to 5 substituents selected from an alkoxy group on the phenyl ring: or substituted by two (C _1-6 ) alkyl groups which may be the same or different A di (C _1-6 ) alkylphosphonyl group is shown. R ³ and R ⁴ may be the same or different, and a hydrogen atom: a cyano group:
(C _1-6 ) alkyl group: halo (C _1-6 ) alkyl group: (C _3-6 ) cycloalkyl group: cyano (C _1-6 ) alkyl group: (C _2-6 ) alkenyl group: (C _2-6 ) Cycloalkenyl group: (C _1-6 ) alkoxy group: halo (C _1-6 ) alkoxy group: (C _1-6 ) alkylthio group:
Halo (C _1-6 ) alkylthio group: (C _1-6 ) alkylsulfinyl group: (C _1-6 ) alkylsulfonyl group: (C _2-6 ) alkenylthio group: (C _2-6 ) alkynylthio group: (C _1-6 ) alkoxy (C
_1-6 ) alkyl group: (C _1-6 ) alkoxy (C _1-6 ) alkylthio group: (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkylsulfonyl (C _{1 -6} ) Alkyl group: (C _3-6 ) Cycloalkylthio group: (C _1-6 ) alkoxycarbonyl (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonylthio group : Phenyl group: may be the same or different, and may be a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkylsulfinyl group, (C _1-6 ) alkylsulfonyl group, aminocarbonyl group, may be the same or different, a mono or selected from a (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Disubstituted aminocarbonyl group, cyano (C _1-6 ) alkoxy group, (C _1-6 ) alkoxycarbonyloxy group, amino group, may be the same or different, formyl group, (C _1-6 ) alkyl group or ( C _1-6 ) mono- or di-substituted amino group having a substituent selected from an alkylcarbonyl group, (C _1-6 ) alkoxycarbonyl group, aminocarbonyloxy group, may be the same or different (C _1-6 ) A mono- or di-substituted aminocarbonyloxy group having a substituent selected from an alkyl group, Dioxy group, a phenyl group, which may be the same or different, a halogen atom, (C
_1-6 ) a phenyl group having 1 to 5 substituents selected from an alkyl group or a (C _1-6 ) alkoxy group, a phenoxy group,
Phenoxy groups which may be the same or different and have 1 to 5 substituents selected from a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group,
Phenyl (C _1-6 ) alkyl group, which may be the same or different,
Phenyl (C _1-6 having 1 to 5 substituents selected from halogen atom, cyano group, nitro group, (C _1-6 ) alkyl group or halo (C _1-6 ) alkyl group on the phenyl ring. ) Alkyl group, phenyl (C _1-6 ) alkyloxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, (C _1-6 ).
1 selected from an alkyl group or a halo (C _1-6 ) alkyl group
~ Phenyl having 5 substituents on the phenyl ring (C _1-6 )
Alkyloxy group, morpholino group, one or more (C _1-6 ) morpholino group substituted by an alkyl group, pyrimidinyloxy group, one or more (C _1-6 ) may be the same or different. A pyrimidinyloxy group substituted with an alkyl group, a morpholinocarbonyl group, one or more morpholinocarbonyl groups substituted with one or more (C _1-6 ) alkyl groups, or bonded to an adjacent carbon atom (C _3-4 ) Phenyl group having 1 to 5 substituents selected from alkylene group: phenyl (C _1-6 ) alkylthio group: may be the same or different, (C _1-6 ) alkyl group or halo ( A phenyl (C _1-6 ) alkylthio group having 1 to 5 substituents selected from C _1-6 ) alkyl groups on the phenyl ring:
Phenylsulfonyl group: may be the same or different, (C
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, phenylsulfonyl group: phenylsulfonyl (C _1-6 ) alkyl group: same or They may be different and may be a (C _1-6 ) alkyl group or a halo (C
_1-6 ) alkyl group having 1 to 5 substituents selected from alkyl group on the phenyl ring: phenylsulfonyl (C _1-6 ) alkyl group: phenylthio (C _1-6 ) alkyl group: may be the same or different , A (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylthio (C _1-6 ) alkyl group: phenyl (C _{1 -6} ) alkylthio (C _1-6 ) alkyl group: may be the same or different,
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring.
_1-6 ) _Alkylthio (C _1-6 ) alkyl group: amino (C _1-6 ) alkyl group: may be the same or different, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkylcarbonyl group,
Phenylcarbonyl group, which may be the same or different, (C
_1-6 ) an alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylcarbonyl group, a phenyl group, or a mono- or di-benzyl group selected from a benzyl group. Substituted amino (C _1-6 ) alkyl group: furfurylthio group: furfurylthio (C _1-6 ) alkyl group: morpholino
(C _1-6) alkyl group: or one or more identical or different and good (C _1-6) morpholino substituted by alkyl group (C _1-6)
Alkyl group: -CO-R ⁶ (wherein, R ⁶ is a (C _1-6 ) alkyl group; halo (C _1-6 ) alkyl group; (C _1-6 ) alkoxy group; halo (C _1-6 ) alkoxy group; (C
_1-6 ) alkylthio group; halo (C _1-6 ) alkylthio group; amino group; may be the same or different and selected from (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group or phenyl group A mono- or di-substituted amino group having a substituted group; a phenyl group; which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group , (C _1-6 ).
Alkoxy group, halo (C _1-6 ) alkoxy group, amino group, the same or different, and having a substituent selected from (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Or a di-substituted amino group, a phenyl group, the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ).
A phenyl group having 1 to 5 substituents selected from alkyl groups, a phenoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _{1 -6} ) A phenoxy group having 1 to 5 substituents selected from an alkyl group, a benzyl group, a benzyloxy group, which may be the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) 1 to 3 selected from alkyl groups
A benzyloxy group having 5 substituents on the phenyl ring, a pyridyloxy group, which may be the same or different and is selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. 1 to 5 substituents selected from a pyridyloxy group having 1 to 4 substituents, a methylenedioxy group, or a (C _3-4 ) alkylene group bonded to an adjacent carbon atom. Phenyl group; benzyloxy group; may be the same or different, halogen atom, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C
_1-6 ) alkoxy group, (C _1-6 ) alkylthio group or halo (C
_1-6 ) Benzyloxy group having 1 to 5 substituents selected from alkylthio group on the phenyl ring; or the same or different, selected from 1 to 3 oxygen atom, sulfur atom or nitrogen atom On the heterocycle, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C
5-6 membered heterocyclic group which may have a substituent selected from _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group is shown. ): Amino group: may be the same or different, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, ( C _1-6 ) alkoxy (C _1-6 ) alkyl group, di (C _1-6 ) alkoxy (C _1-6 ) alkyl group, amino
(C _1-6 ) alkyl group, which may be the same or different (C _1-6 ) alkyl group-substituted mono or di (C _1-6 ) alkylamino (C _1-6 ) alkyl group, phenyl group, They may be the same or different and are selected from a halogen atom, a (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group or a halo (C _1-6 ) alkyl group. a phenyl group having 1 to 5 substituents, pyridyl (C _{1- 6)} alkyl group or morpholino (C _1-6) mono- or di-substituted amino group having a substituent selected from an alkyl group: phenyl (C _{1 -6} ) Alkyl group: the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or 1 to halo (C _1-6 ) alkylthio group selected from Phenyl (C _1-6 ) alkyl group having 5 substituents on the phenyl ring: phenyl (C _2-6 ).
Alkenyl group: phenyl (which may be the same or different and has 1 to 5 substituents selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group on the phenyl ring. C _2-6 ) alkenyl group: naphthyl group: 5-7 membered heterocyclic group having 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom, which may be the same or different: or said 5 7-membered heterocyclic group and benzene ring or (C
_4-6 ) represents a heterocyclic group in which a cycloalkane ring is condensed, and these heterocyclic groups may be the same or different, and a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkoxycarbonyl group, phenyl group,
1 selected from halogen atoms which may be the same or different
It can also have one or more substituents selected from a phenyl group having 5 to 5 substituents, a benzyl group, a pyridyl group, a pyrimidyl group or a dioxolane group. Also, R ³ and
R ⁴ together may be interrupted by an oxygen atom, a sulfur atom, a nitrogen atom, a carbonyl group, or a nitrogen atom substituted by a (C _1-6 ) alkyl group or a phenyl group (C _1-6 ).
Alkylene group or (C _2-6 ) represents an alkenylene group, the alkylene group or alkenylene group may be the same or different on the alkylene chain or on the alkenylene chain, (C _1-6 ) alkyl group, halo (C _{1- 6} ) It may have one or more substituents selected from an alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group, and is condensed with a benzene ring to form a condensed ring group. It can also be formed. ] The benzyl hydrazone derivative represented by these. 2. X is CH--OR^Five (In the formula, R^FiveIs (C_1-6) Indicates an alkyl group. ), Or embedded image N to OR^Five (In the formula, R^FiveIs the same as above. ), And Y is (C_1-6) Alkoxy group, (C_1-6) Alkylthio group, ami
Group or may be the same or different (C_1-6) Alkyl group
A mono- or di-substituted amino group substituted by, Z may be the same or different, a halogen atom, (C_1-6)
Rukiru group or halo (C_1-6) Represents an alkyl group, m is 0 to 4
Indicates the integer of R¹Is a hydrogen atom, (C_1-6) Alkyl group or halo (C_1-6) Archi
R group, R²Is (C_1-6) Alkylcarbonyl group: halo (C_1-6) Alkyl
Carbonyl group: (C_1-6) Alkylsulfonyl group: halo (C
_1-6) Alkylsulfonyl group: aminocarbonyl group: same
Or it may be different, a formyl group or (C_1-6) Alkyl group
A mono- or di-substituted amino having a substituent selected from
Nocarbonyl group: (C_1-6) Alkoxycarbonyl group: (C
_1-6) Alkoxycarbonyl (C_1-6) Alkylcarbonyl
Group: Cyano (C_1-6) Alkylcarbonyl group: (C_1-6) Archi
Ruthiocarbonyl group: phenylcarbonyl group: same or
May be different, halogen atom, (C_1-6) Alkyl group, Ha
B (C_1-6) Alkyl group, (C_1-6) Alkoxy group or halo (C
_1-6) Having 1 to 5 substituents selected from alkoxy groups
Phenylcarbonyl group: Phenyl (C_1-6) Alkyl
Rubonyl group: may be the same or different, a halogen atom,
(C_1-6) Alkyl group, halo (C_1-6) Alkyl group, (C_1-6) Al
Coxy group or halo (C_1-6) 1 selected from alkoxy groups
Phenyl having 5 to 5 substituents on the phenyl ring (C_1-6)
Alkylcarbonyl group: Phenoxycarbonyl group: Identical
Or may be different, a halogen atom, (C_1-6) Alkyl
Group, halo (C_1-6) Alkyl group, (C_1-6) Alkoxy group or ha
B (C_1-6) 1-5 substituents selected from alkoxy groups
With a phenoxycarbonyl group on the phenyl ring: Ben
Zyloxycarbonyl group: may be the same or different,
Rogen atom, (C_1-6) Alkyl group, halo (C_1-6) Alkyl
Group, (C_1-6) Alkoxy group or halo (C_1-6) Is it an alkoxy group?
Having 1 to 5 substituents selected from on the phenyl ring
Benzyloxycarbonyl group: or the same or different
Good two (C_1-6) Di (C_1-6)
Represents an alkylphosphonyl group, R³And R^FourMay be the same or different, and a hydrogen atom: cyano
Group: (C_1-6) Alkyl group: halo (C_1-6) Alkyl group: (C_3-6)
Cycloalkyl group: Cyano (C_1-6) Alkyl group: (C_2-6)
Lucenyl group: (C_3-6) Cycloalkenyl group: (C_1-6) Arco
Xyl group: halo (C_1-6) Alkoxy group: (C_1-6) Alkylthio
Group: halo (C_1-6) Alkylthio group: (C_1-6) Alkyl sulf
Inyl group: (C_1-6) Alkylsulfonyl group: (C_2-6) Arche
Nylthio group: (C_2-6) Alkynylthio group: (C_1-6) Arkoki
Shi (C_1-6) Alkyl group: (C_1-6) Alkoxy (C_1-6) Alkyl
Thio group: (C_1-6) Alkylthio (C_1-6) Alkyl group: (C_1-6)
Alkylsulfonyl (C_1-6) Alkyl group: (C_3-6) Cycloa
Rukiruthio group: (C_1-6) Alkoxycarbonyl (C_1-6) Al
Kirchio (C_1-6) Alkyl group: (C_1-6) Alkoxycarboni
Ruthio group: phenyl group: may be the same or different, halo
Gen atom, cyano group, nitro group, (C_1-6) Alkyl group, Ha
B (C_1-6) Alkyl group, (C_1-6) Alkoxy group, halo (C_1-6)
Alkoxy group, (C_1-6) Alkylthio group, halo (C_1-6) Al
Kirthio group, (C_1-6) Alkylsulfinyl group, (C_1-6)
Alkylsulfonyl group, aminocarbonyl group, same or different
May be, (C_1-6) Alkyl group or (C_1-6) Alkyl
Mono- or di-substituted aminocarl selected from rubonyl group
Bonyl group, cyano (C_1-6) Alkoxy group, (C_1-6) Arkoki
Cycarbonyloxy group, amino group, the same or different
Well, formyl group, (C_1-6) Alkyl group or (C_1-6) Archi
Or having a substituent selected from the group
Di-substituted amino group, (C_1-6) Alkoxycarbonyl group, amino
Nocarbonyloxy group, which may be the same or different (C_1-6)
Mono- or di-positions having substituents selected from alkyl groups
Substituted aminocarbonyloxy group, methylenedioxy group,
Phenyl group, which may be the same or different, a halogen atom, (C
_1-6) Alkyl group or (C_1-6) Selected from alkoxy groups
A phenyl group having 1 to 5 substituents, a phenoxy group,
They may be the same or different and may be a halogen atom, a cyano group, or
Toro group, (C_1-6) Alkyl group or halo (C_1-6) Is it an alkyl group?
A phenoxy group having 1 to 5 substituents selected from
Phenyl (C_1-6) Alkyl groups, which may be the same or different,
Halogen atom, cyano group, nitro group, (C_1-6) Alkyl group
Or halo (C_1-6) 1 to 5 units selected from alkyl groups
Phenyl having a substituent on the phenyl ring (C_1-6) Alkyl
Group, phenyl (C_1-6) Alkyloxy groups, the same or different
, Halogen atom, cyano group, nitro group, (C_1-6)
Alkyl group or halo (C_1-6) 1 selected from alkyl groups
Phenyl having 5 to 5 substituents on the phenyl ring (C_1-6)
Alkyloxy group, morpholino group, one or more same or different
Can be (C_1-6) Morpho substituted with an alkyl group
Rino group, pyrimidinyloxy group, 1 or more same or different
Good (C_1-6) Pyrimidi substituted by an alkyl group
Nyloxy group, morpholinocarbonyl group, one or more identical
Or may be different (C_1-6) Substituted by an alkyl group
Bonds with morpholino carbonyl groups or adjacent carbon atoms.
Combined (C_3-4) 1 to 5 units selected from alkylene groups
Phenyl group having a substituent: phenyl (C_1-6) Alkylthio
Group: may be the same or different, (C_1-6) Alkyl group or ha
B (C_1-6) 1 to 5 substituents selected from alkyl groups
Phenyl on the phenyl ring (C_1-6) Alkylthio group:
Phenylsulfonyl group: may be the same or different, (C
_1-6) Alkyl group or halo (C_1-6) Selected from alkyl groups
Having 1 to 5 substituents on the phenyl ring
Rufonyl group: Phenylsulfonyl (C_1-6) Alkyl group: same
One or different, (C_1-6) Alkyl group or halo (C
_1-6) 1 to 5 substituents selected from alkyl groups are
Phenylsulfonyl (C on the nyl ring_1-6) Alkyl
Group: Phenylthio (C_1-6) Alkyl groups: the same or different
Also good, (C_1-6) Alkyl group or halo (C_1-6) Is it an alkyl group?
Having 1 to 5 substituents selected from on the phenyl ring
Phenylthio (C_1-6) Alkyl group: Phenyl (C_1-6) Archi
Lucio (C_1-6) Alkyl group: the same or different, (C
_1-6) Alkyl group or halo (C_1-6) Selected from alkyl groups
Phenyl having 1 to 5 substituents on the phenyl ring (C
_1-6) Alkylthio (C_1-6) Alkyl group: amino (C_1-6) Al
Kill group: may be the same or different, (C_1-6) An alkyl group,
Hello (C_1-6) Alkyl group, (C_1-6) An alkylcarbonyl group,
Phenylcarbonyl group, which may be the same or different, (C
_1-6) Alkyl group or halo (C_1-6) Selected from alkyl groups
Having 1 to 5 substituents on the phenyl ring
Selected from a carbonyl group, a phenyl group, or a benzyl group
Mono- or di-substituted amino (C _1-6) Alkyl group: Furfuryl
Thio group: Furfurylthio (C_1-6) Alkyl group: morpholino
(C_1-6) Alkyl group: or one or more same or different
I (C_1-6) Morpholino (C_1-6)
Alkyl group: amino group: may be the same or different, (C
_1-6) Alkyl group, halo (C_1-6) Alkyl group, (C_2-6) Arche
Nyl group, (C_2-6) Alkynyl group, (C_1-6) Alkoxy (C_1-6)
Alkyl group, di (C_1-6) Alkoxy (C_1-6) Alkyl group,
Mino (C_1-6) Alkyl groups, which may be the same or different (C_1-6)
Mono or di (C_1-6) Alkyl
Amino (C_1-6) Alkyl group, phenyl group, same or different
May be a halogen atom, (C_1-6) Alkyl group, (C_1-6)
Lucoxy group, (C_1-6) Alkylthio group or halo (C_1-6) Al
Phenyl having 1 to 5 substituents selected from the group
Group, pyridyl (C_1-6) Alkyl group or morpholino (C_1-6)
Mono- or di-positions having substituents selected from alkyl groups
Substituted amino group: phenyl (C_1-6) Alkyl group: same or different
Halogen atom, (C_1-6) Alkyl group, halo (C
_1-6) Alkyl group, (C_1-6) Alkoxy group, halo (C_1-6) Al
Coxy group, (C_1-6) Alkylthio group or halo (C_1-6) Archi
Phenyl ring with 1 to 5 substituents selected from ruthio groups
Phenyl (C_1-6) Alkyl group: Phenyl (C_2-6)
Alkenyl group: same or different, halogen atom
Child, (C_1-6) Alkyl group or halo (C_1-6) Select from alkyl groups
Fe having 1 to 5 substituents selected on the phenyl ring
Nil (C_2-6) Alkenyl group: naphthyl group: same or different
Can be selected from oxygen atom, sulfur atom or nitrogen atom
5- to 7-membered heterocycle having 1 to 3 heteroatoms
Group: or the 5- to 7-membered heterocyclic group and a benzene ring or (C
_4-6) Represents a heterocyclic group in which a cycloalkane ring is condensed.
The heterocyclic groups may be the same or different,
Child, cyano group, nitro group, (C_1-6) Alkyl group, halo (C
_1-6) Alkyl group, (C_1-6) Alkoxy group, halo (C_1-6) Al
Coxy group, (C_1-6) Alkylthio group, halo (C_1-6) Alkyl
Thio group, (C_1-6) Alkoxycarbonyl group, phenyl group,
1 selected from halogen atoms which may be the same or different
A phenyl group having 5 to 5 substituents, a benzyl group, a pyri group
Selected from a dil group, a pyrimidyl group or a dioxolane group
It can also have one or more substituents. Also, R³as well as
R^FourTogether are oxygen atom, sulfur atom, nitrogen atom, cal
Bonyl group, or (C_1-6) For alkyl or phenyl groups
It may be interrupted by a more substituted nitrogen atom (C_1-6)
Alkylene group or (C_2-6) Represents an alkenylene group,
A xylene group or an alkenylene group is on the alkylene chain or
They may be the same or different on the kenylene chain, (C_1-6) Archi
Lu group, halo (C_1-6) Alkyl group, (C_1-6) Alkoxy group or
Hello (C_1-6) One or more substitutions selected from alkoxy groups
It may have a group and is condensed with a benzene ring to form a condensed ring group.
The group according to claim 1, wherein each group is represented by
Benzylhydrazone derivative. 3. X is CH—OR ⁵ (in the formula, R ⁵ represents a (C _1-6 ) alkyl group), or N—OR ⁵ (in the formula, R ⁵ Is the same as above.), And Y represents a (C _1-6 ) alkoxy group, an amino group or a mono- or di-substituted amino group substituted by the same or different (C _1-6 ) alkyl group. , Z may be the same or different, and represent a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group, m represents an integer of 0, R ¹ represents a hydrogen atom, R ² represents a (C _1-6 ) alkylcarbonyl group, R ³ and R ⁴ may be the same or different, (C _1-6 ) alkyl group: (C _1-6 ) alkylthio group: phenyl group: the same Or may be different, a halogen atom, a cyano group, a nitro group, (C
_1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _{1- 6)} alkylthio groups, (C _1-6) alkylsulfinyl group, (C _1-6) a phenyl group having an alkylsulfonyl group, or a 1 to 5 substituents selected from methylenedioxy group: the same or different A 5- to 7-membered heterocyclic group having 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom: or a 5- to 7-membered heterocyclic group and a benzene ring or (C _4-6 ). Represents a heterocyclic group in which a cycloalkane ring is condensed, and these heterocyclic groups may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C _1-6 ). Alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group,
A halo (C _1-6 ) alkylthio group, a (C _1-6 ) alkoxycarbonyl group, a phenyl group, a phenyl group having 1 to 5 substituents selected from the same or different halogen atoms, a benzyl group, The benzylhydrazone derivative according to claim 2, which represents each group which can have one or more substituents selected from a pyridyl group, a pyrimidyl group or a dioxolane group. 4. 1-3 selected from an oxygen atom, a sulfur atom or a nitrogen atom, which may be the same or different, represented by R ³ and R ^4.
5-7 membered heterocyclic group having 5 heteroatoms or said 5-7
A heterocyclic ring in which a membered heterocyclic group and a benzene ring or a cycloalkane ring are condensed, furan, thiophene, pyrrole, pyrazole, imidazole, triazole, oxazole,
Thiazole, pyridine, pyridazine, pyrimidine, pyrazine, pyrrolidine, piperidine, morpholine, thiomorpholine, piperazine, hexamethyleneimine, tetrahydroquinoline, tetrahydroisoquinoline, 2,3-dihydro-1,4-benzoxazine, octahydro-
The benzylhydrazone derivative according to claim 3, which is 1,4-benzoxazine or indole. 5. A compound represented by the general formula (II): [In the formula, X is: CH to OR ⁵ (in the formula, R ⁵ represents a (C _1-6 ) alkyl group), or: N to OR ⁵ (wherein, R ⁵ is The same as the above). Y represents a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group, an amino group or a mono- or di-substituted amino group substituted by the same or different (C _1-6 ) alkyl group. Z may be the same or different and may be a halogen atom, a (C _1-6 ) alkyl group or a halo (C 1
_1-6 ) alkyl group, and m represents an integer of 0-4. R ¹ represents a hydrogen atom, a (C _1-6 ) alkyl group or a (C _1-6 ) haloalkyl group, and Hal represents a halogen atom. ] And a compound represented by the general formula (III): [In the formula, R ² is a formyl group: (C _1-6 ) alkylcarbonyl group: halo (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylsulfonyl group: halo (C _1-6 ) alkylsulfonyl Group: aminocarbonyl group: mono- or di-substituted aminocarbonyl group, which may be the same or different, and which has a substituent selected from formyl group or (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonyl group : (C _1-6 ) alkoxycarbonyl (C _1-6 ) alkylcarbonyl group: cyano (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylthiocarbonyl group: phenylcarbonyl group: may be the same or different , Halogen atom, (C
_1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group
Phenylcarbonyl group having 5 substituents: phenyl
(C _1-6 ) alkylcarbonyl group: may be the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group or a halo ( A phenyl (C _1-6 ) alkylcarbonyl group having 1 to 5 substituents selected from C _1-6 ) alkoxy groups on the phenyl ring: a phenoxycarbonyl group: the same or different, a halogen atom, ( C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ).
Phenoxycarbonyl group having 1 to 5 substituents selected from an alkoxy group or a halo (C _1-6 ) alkoxy group on the phenyl ring: benzyloxycarbonyl group: may be the same or different, a halogen atom, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group or halo (C 1
_1-6 ) a benzyloxycarbonyl group having 1 to 5 substituents selected from an alkoxy group on the phenyl ring: or substituted by two (C _1-6 ) alkyl groups which may be the same or different A di (C _1-6 ) alkylphosphonyl group is shown. R ³ and R ⁴ may be the same or different, and a hydrogen atom: a cyano group:
(C _1-6 ) alkyl group: halo (C _1-6 ) alkyl group: (C _3-6 ) cycloalkyl group: cyano (C _1-6 ) alkyl group: (C _2-6 ) alkenyl group: (C _3-6 ) Cycloalkenyl group: (C _1-6 ) alkoxy group: halo (C _1-6 ) alkoxy group: (C _1-6 ) alkylthio group:
Halo (C _1-6 ) alkylthio group: (C _1-6 ) alkylsulfinyl group: (C _1-6 ) alkylsulfonyl group: (C _2-6 ) alkenylthio group: (C _2-6 ) alkynylthio group: (C _1-6 ) alkoxy (C
_1-6 ) alkyl group: (C _1-6 ) alkoxy (C _1-6 ) alkylthio group: (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkylsulfonyl (C _{1 -6} ) Alkyl group: (C _3-6 ) Cycloalkylthio group: (C _1-6 ) alkoxycarbonyl (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonylthio group : Phenyl group: may be the same or different, and may be a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkylsulfinyl group, (C _1-6 ) alkylsulfonyl group, aminocarbonyl group, may be the same or different, a mono or selected from a (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Disubstituted aminocarbonyl group, cyano (C _1-6 ) alkyloxy group, (C _1-6 ) alkoxycarbonyloxy group, amino group, which may be the same or different, formyl group, (C _1-6 ) alkyl group or (C _1-6 ) mono- or di-substituted amino group having a substituent selected from an alkylcarbonyl group, (C _1-6 ) alkoxycarbonyl group, aminocarbonyloxy group, may be the same or different (C _1-6 )
A mono- or di-substituted aminocarbonyloxy group having a substituent selected from an alkyl group, a methylenedioxy group, a phenyl group, which may be the same or different, a halogen atom, (C
_1-6 ) a phenyl group having 1 to 5 substituents selected from an alkyl group or a (C _1-6 ) alkoxy group, a phenoxy group,
Phenoxy groups which may be the same or different and have 1 to 5 substituents selected from a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group,
Phenyl (C _1-6 ) alkyl group, which may be the same or different,
Phenyl (C _1-6 having 1 to 5 substituents selected from halogen atom, cyano group, nitro group, (C _1-6 ) alkyl group or halo (C _1-6 ) alkyl group on the phenyl ring. ) Alkyl group, phenyl (C _1-6 ) alkyloxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, (C _1-6 ).
1 selected from an alkyl group or a halo (C _1-6 ) alkyl group
~ Phenyl having 5 substituents on the phenyl ring (C _1-6 )
Alkyloxy group, morpholino group, one or more (C _1-6 ) morpholino group substituted by an alkyl group, pyrimidinyloxy group, one or more (C _1-6 ) may be the same or different. A pyrimidinyloxy group substituted with an alkyl group, a morpholinocarbonyl group, one or more morpholinocarbonyl groups substituted with one or more (C _1-6 ) alkyl groups, or bonded to an adjacent carbon atom (C _3-4 ) Phenyl group having 1 to 5 substituents selected from alkylene group: phenyl (C _1-6 ) alkylthio group: may be the same or different, (C _1-6 ) alkyl group or halo ( A phenyl (C _1-6 ) alkylthio group having 1 to 5 substituents selected from C _1-6 ) alkyl groups on the phenyl ring:
Phenylsulfonyl group: may be the same or different, (C
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, phenylsulfonyl group: phenylsulfonyl (C _1-6 ) alkyl group: same or They may be different and may be a (C _1-6 ) alkyl group or a halo (C
_1-6 ) alkyl group having 1 to 5 substituents selected from alkyl group on the phenyl ring: phenylsulfonyl (C _1-6 ) alkyl group: phenylthio (C _1-6 ) alkyl group: may be the same or different , A (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylthio (C _1-6 ) alkyl group: phenyl (C _{1 -6} ) alkylthio (C _1-6 ) alkyl group: may be the same or different,
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring.
_1-6 ) _Alkylthio (C _1-6 ) alkyl group: amino (C _1-6 ) alkyl group: may be the same or different, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkylcarbonyl group,
Phenylcarbonyl group, which may be the same or different, (C
_1-6 ) an alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylcarbonyl group, a phenyl group, or a mono- or di-benzyl group selected from a benzyl group. Substituted amino (C _1-6 ) alkyl group: furfurylthio group: furfurylthio (C _1-6 ) alkyl group: morpholino
(C _1-6) alkyl group: or one or more identical or different and good (C _1-6) morpholino substituted by alkyl group (C _1-6)
Alkyl group: -CO-R ⁶ (wherein, R ⁶ is a (C _1-6 ) alkyl group; halo (C _1-6 ) alkyl group; (C _1-6 ) alkoxy group; halo (C _1-6 ) alkoxy group; (C
_1-6 ) alkylthio group; halo (C _1-6 ) alkylthio group; amino group; may be the same or different and selected from (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group or phenyl group A mono- or di-substituted amino group having a substituted group; a phenyl group; which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group , (C _1-6 ).
Alkoxy group, halo (C _1-6 ) alkoxy group, amino group, the same or different, and having a substituent selected from (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Or a di-substituted amino group, a phenyl group, the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ).
A phenyl group having 1 to 5 substituents selected from alkyl groups, a phenoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _{1 -6} ) A phenoxy group having 1 to 5 substituents selected from an alkyl group, a benzyl group, a benzyloxy group, which may be the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) 1 to 3 selected from alkyl groups
A benzyloxy group having 5 substituents on the phenyl ring, a pyridyloxy group, which may be the same or different and is selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. 1 to 5 substituents selected from a pyridyloxy group having 1 to 4 substituents, a methylenedioxy group, or a (C _3-4 ) alkylene group bonded to an adjacent carbon atom. Phenyl group; benzyloxy group; may be the same or different, halogen atom, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C
_1-6 ) alkoxy group, (C _1-6 ) alkylthio group or halo (C
_1-6 ) Benzyloxy group having 1 to 5 substituents selected from alkylthio group on the phenyl ring; or the same or different, selected from 1 to 3 oxygen atom, sulfur atom or nitrogen atom On the heterocycle, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C
5-6 membered heterocyclic group which may have a substituent selected from _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group is shown. ): Amino group: may be the same or different, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, ( C _1-6 ) alkoxy (C _1-6 ) alkyl group, di (C _1-6 ) alkoxy (C _1-6 ) alkyl group, amino
(C _1-6 ) alkyl group, which may be the same or different (C _1-6 ) alkyl group-substituted mono or di (C _1-6 ) alkylamino (C _1-6 ) alkyl group, phenyl group, They may be the same or different and are selected from a halogen atom, a (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group or a halo (C _1-6 ) alkyl group. A mono- or di-substituted amino group having a substituent selected from a phenyl group having 1 to 5 substituents, a pyridyl (C _1-6 ) alkyl group or a morpholino (C _1-6 ) alkyl group: phenyl (C _{1 -6} ) Alkyl group: the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or 1 to halo (C _1-6 ) alkylthio group selected from Phenyl (C _1-6 ) alkyl group having 5 substituents on the phenyl ring: phenyl (C _2-6 ).
Alkenyl group: phenyl (which may be the same or different and has 1 to 5 substituents selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group on the phenyl ring. C _2-6 ) alkenyl group: naphthyl group: 5-7 membered heterocyclic group having 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom, which may be the same or different: or said 5 7-membered heterocyclic group and benzene ring or (C
_4-6 ) represents a heterocyclic group in which a cycloalkane ring is condensed, and these heterocyclic groups may be the same or different, and a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkoxycarbonyl group, phenyl group,
1 selected from halogen atoms which may be the same or different
It can also have one or more substituents selected from a phenyl group having 5 to 5 substituents, a benzyl group, a pyridyl group, a pyrimidyl group or a dioxolane group. Also, R ³ and
R ⁴ together may be interrupted by an oxygen atom, a sulfur atom, a nitrogen atom, a carbonyl group, or a nitrogen atom substituted by a (C _1-6 ) alkyl group or a phenyl group (C _1-6 ).
Alkylene group or (C _2-6 ) represents an alkenylene group, the alkylene group or alkenylene group may be the same or different on the alkylene chain or on the alkenylene chain, (C _1-6 ) alkyl group, halo (C _{1- 6} ) It may have one or more substituents selected from an alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group, and is condensed with a benzene ring to form a condensed ring group. It can also be formed. ] The compound of the general formula (I) characterized by reacting with a compound represented by [In the formula, X, Y, Z, m, R ¹ , R ² , R ³ and R ⁴ are the same as defined above. ] The manufacturing method of the benzyl hydrazone derivative represented by these. 6. A compound represented by the general formula (I ′): [In the formula, X is: CH to OR ⁵ (in the formula, R ⁵ represents a (C _1-6 ) alkyl group), or: N to OR ⁵ (wherein, R ⁵ is The same as the above). Y ¹ represents a (C _1-6 ) alkoxy group or a (C _1-6 ) alkylthio group. Z may be the same or different and represents a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group, and m represents an integer of 0-4. R ¹ represents a hydrogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. R ² is a formyl group: (C _1-6 ) alkylcarbonyl group: halo (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylsulfonyl group: halo (C _1-6 ) alkylsulfonyl group: aminocarbonyl Group: mono- or di-substituted aminocarbonyl group which may be the same or different and has a substituent selected from formyl group or (C _1-6 ) alkyl group: (C _1-6 ).
Alkoxycarbonyl group: (C _1-6 ) alkoxycarbonyl
(C _1-6 ) alkylcarbonyl group: cyano (C _1-6 ) alkylcarbonyl group: (C _1-6 ) alkylthiocarbonyl group: phenylcarbonyl group: may be the same or different, a halogen atom, (C _1-6 ) Alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ).
A phenylcarbonyl group having 1 to 5 substituents selected from an alkoxy group or a halo (C _1-6 ) alkoxy group: a phenyl (C _1-6 ) alkylcarbonyl group: the same or different, a halogen atom, (C _1-6 ) alkyl group, halo (C _1-6 ).
Phenyl (C _1-6 ) alkylcarbonyl group having 1 to 5 substituents on the phenyl ring selected from alkyl group, (C _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group: phenoxy Carbonyl group: may be the same or different, a halogen atom, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C
_1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group having 1 to 5 substituents on the phenyl ring, phenoxycarbonyl group: benzyloxycarbonyl group: may be the same or different, halogen 1 to 5 substituents selected from atom, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group A benzyloxycarbonyl group having R on the phenyl ring:
Alternatively, it represents a di (C _1-6 ) alkylphosphonyl group substituted with a (C _1-6 ) alkyl group which may be the same or different. R ³ and
R ^{4 s} may be the same or different, and a hydrogen atom: a cyano group: (C
_1-6 ) alkyl group: halo (C _1-6 ) alkyl group: (C _3-6 ) cycloalkyl group: cyano (C _1-6 ) alkyl group: (C _2-6 ) alkenyl group: (C _{3- 6} ) Cycloalkenyl group: (C _1-6 ) alkoxy group: halo (C _1-6 ) alkoxy group: (C _1-6 ) alkylthio group:
Halo (C _1-6 ) alkylthio group: (C _1-6 ) alkylsulfinyl group: (C _1-6 ) alkylsulfonyl group: (C _2-6 ) alkenylthio group: (C _2-6 ) alkynylthio group: (C _1-6 ) alkoxy (C
_1-6 ) alkyl group: (C _1-6 ) alkoxy (C _1-6 ) alkylthio group: (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkylsulfonyl (C _{1 -6} ) Alkyl group: (C _3-6 ) Cycloalkylthio group: (C _1-6 ) alkoxycarbonyl (C _1-6 ) alkylthio (C _1-6 ) alkyl group: (C _1-6 ) alkoxycarbonylthio group : Phenyl group: may be the same or different, and may be a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkylsulfinyl group, (C _1-6 ) alkylsulfonyl group, aminocarbonyl group, may be the same or different, a mono or selected from a (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Disubstituted aminocarbonyl group, cyano (C _1-6 ) alkoxy group, (C _1-6 ) alkoxycarbonyloxy group, amino group, may be the same or different, formyl group, (C _1-6 ) alkyl group or ( C _1-6 ) mono- or di-substituted amino group having a substituent selected from an alkylcarbonyl group, (C _1-6 ) alkoxycarbonyl group, aminocarbonyloxy group, may be the same or different (C _1-6 ) A mono- or di-substituted aminocarbonyloxy group having a substituent selected from an alkyl group, Dioxy group, a phenyl group, which may be the same or different, a halogen atom, (C
_1-6 ) a phenyl group having 1 to 5 substituents selected from an alkyl group or a (C _1-6 ) alkoxy group, a phenoxy group,
Phenoxy groups which may be the same or different and have 1 to 5 substituents selected from a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group,
Phenyl (C _1-6 ) alkyl group, which may be the same or different,
Phenyl (C _1-6 having 1 to 5 substituents selected from halogen atom, cyano group, nitro group, (C _1-6 ) alkyl group or halo (C _1-6 ) alkyl group on the phenyl ring. ) Alkyl group, phenyl (C _1-6 ) alkyloxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, (C _1-6 ).
1 selected from an alkyl group or a halo (C _1-6 ) alkyl group
~ Phenyl having 5 substituents on the phenyl ring (C _1-6 )
Alkyloxy group, morpholino group, one or more (C _1-6 ) morpholino group substituted by an alkyl group, pyrimidinyloxy group, one or more (C _1-6 ) may be the same or different. A pyrimidinyloxy group substituted with an alkyl group, a morpholinocarbonyl group, one or more morpholinocarbonyl groups substituted with one or more (C _1-6 ) alkyl groups, or bonded to an adjacent carbon atom (C _3-4 ) Phenyl group having 1 to 5 substituents selected from alkylene group: phenyl (C _1-6 ) alkylthio group: may be the same or different, (C _1-6 ) alkyl group or halo ( A phenyl (C _1-6 ) alkylthio group having 1 to 5 substituents selected from C _1-6 ) alkyl groups on the phenyl ring:
Phenylsulfonyl group: may be the same or different, (C
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, phenylsulfonyl group: phenylsulfonyl (C _1-6 ) alkyl group: same or They may be different and may be a (C _1-6 ) alkyl group or a halo (C
_1-6 ) alkyl group having 1 to 5 substituents selected from alkyl group on the phenyl ring: phenylsulfonyl (C _1-6 ) alkyl group: phenylthio (C _1-6 ) alkyl group: may be the same or different , A (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylthio (C _1-6 ) alkyl group: phenyl (C _{1 -6} ) alkylthio (C _1-6 ) alkyl group: may be the same or different,
_1-6 ) alkyl group or halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring.
_1-6 ) _Alkylthio (C _1-6 ) alkyl group: amino (C _1-6 ) alkyl group: may be the same or different, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkylcarbonyl group,
Phenylcarbonyl group, which may be the same or different, (C
_1-6 ) an alkyl group or a halo (C _1-6 ) alkyl group having 1 to 5 substituents on the phenyl ring, a phenylcarbonyl group, a phenyl group, or a mono- or di-benzyl group selected from a benzyl group. Substituted amino (C _1-6 ) alkyl group: furfurylthio group: furfurylthio (C _1-6 ) alkyl group: morpholino
(C _1-6) alkyl group: or one or more identical or different and good (C _1-6) morpholino substituted by alkyl group (C _1-6)
Alkyl group: -CO-R ⁶ (wherein, R ⁶ is a (C _1-6 ) alkyl group; halo (C _1-6 ) alkyl group; (C _1-6 ) alkoxy group; halo (C _1-6 ) alkoxy group; (C
_1-6 ) alkylthio group; halo (C _1-6 ) alkylthio group; amino group; may be the same or different and selected from (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group or phenyl group A mono- or di-substituted amino group having a substituted group; a phenyl group; which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group , (C _1-6 ).
Alkoxy group, halo (C _1-6 ) alkoxy group, amino group, the same or different, and having a substituent selected from (C _1-6 ) alkyl group or (C _1-6 ) alkylcarbonyl group Or a di-substituted amino group, a phenyl group, the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ).
A phenyl group having 1 to 5 substituents selected from alkyl groups, a phenoxy group, which may be the same or different, a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group or a halo (C _{1 -6} ) A phenoxy group having 1 to 5 substituents selected from an alkyl group, a benzyl group, a benzyloxy group, which may be the same or different, a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) 1 to 3 selected from alkyl groups
A benzyloxy group having 5 substituents on the phenyl ring, a pyridyloxy group, which may be the same or different and is selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group. 1 to 5 substituents selected from a pyridyloxy group having 1 to 4 substituents, a methylenedioxy group, or a (C _3-4 ) alkylene group bonded to an adjacent carbon atom. Phenyl group; benzyloxy group; may be the same or different, halogen atom, (C _1-6 ) alkyl group,
Halo (C _1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C
_1-6 ) alkoxy group, (C _1-6 ) alkylthio group or halo (C
_1-6 ) Benzyloxy group having 1 to 5 substituents selected from alkylthio group on the phenyl ring; or the same or different, selected from 1 to 3 oxygen atom, sulfur atom or nitrogen atom On the heterocycle, a (C _1-6 ) alkyl group, a halo (C _1-6 ) alkyl group, (C
5-6 membered heterocyclic group which may have a substituent selected from _1-6 ) alkoxy group or halo (C _1-6 ) alkoxy group is shown. ): Amino group: may be the same or different, (C _1-6 ) alkyl group, halo (C _1-6 ) alkyl group, (C _2-6 ) alkenyl group, (C _2-6 ) alkynyl group, ( C _1-6 ) alkoxy (C _1-6 ) alkyl group, di (C _1-6 ) alkoxy (C _1-6 ) alkyl group, amino
(C _1-6 ) alkyl group, which may be the same or different (C _1-6 ) alkyl group-substituted mono or di (C _1-6 ) alkylamino (C _1-6 ) alkyl group, phenyl group, They may be the same or different and are selected from a halogen atom, a (C _1-6 ) alkyl group, a (C _1-6 ) alkoxy group, a (C _1-6 ) alkylthio group or a halo (C _1-6 ) alkyl group. a phenyl group having 1 to 5 substituents, pyridyl (C _1-6) alkyl group or morpholino (C _1-6) mono or di-substituted amino group having a substituent selected from an alkyl group: phenyl (C _1-6 ) alkyl group: may be the same or different, and may be a halogen atom, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group or 1 to halo (C _1-6 ) alkylthio group selected from Phenyl (C _1-6 ) alkyl group having 5 substituents on the phenyl ring: phenyl (C _2-6 ).
Alkenyl group: phenyl (which may be the same or different and has 1 to 5 substituents selected from a halogen atom, a (C _1-6 ) alkyl group or a halo (C _1-6 ) alkyl group on the phenyl ring. C _2-6 ) alkenyl group: naphthyl group: 5-7 membered heterocyclic group having 1 to 3 heteroatoms selected from oxygen atom, sulfur atom or nitrogen atom, which may be the same or different: or said 5 7-membered heterocyclic group and benzene ring or (C
_4-6 ) represents a heterocyclic group in which a cycloalkane ring is condensed, and these heterocyclic groups may be the same or different, and a halogen atom, a cyano group, a nitro group, a (C _1-6 ) alkyl group, a halo (C
_1-6 ) alkyl group, (C _1-6 ) alkoxy group, halo (C _1-6 ) alkoxy group, (C _1-6 ) alkylthio group, halo (C _1-6 ) alkylthio group, (C _1-6 ) Alkoxycarbonyl group, phenyl group,
1 selected from halogen atoms which may be the same or different
It can also have one or more substituents selected from a phenyl group having 5 to 5 substituents, a benzyl group, a pyridyl group, a pyrimidyl group or a dioxolane group. Also, R ³ and
R ⁴ together may be interrupted by an oxygen atom, a sulfur atom, a nitrogen atom, a carbonyl group, or a nitrogen atom substituted by a (C _1-6 ) alkyl group or a phenyl group (C _1-6 ).
Alkylene group or (C _2-6 ) represents an alkenylene group, the alkylene group or alkenylene group may be the same or different on the alkylene chain or on the alkenylene chain, (C _1-6 ) alkyl group, halo (C _{1- 6} ) It may have one or more substituents selected from an alkyl group, a (C _1-6 ) alkoxy group or a halo (C _1-6 ) alkoxy group, and is condensed with a benzene ring to form a condensed ring group. It can also be formed. And a benzylhydrazone derivative represented by the following general formula (IV): embedded image Y ² —H (IV) [wherein Y ² may be an amino group or the same or different.
A mono- or di-substituted amino group substituted with a (C _1-6 ) alkyl group is shown. ] The compound of the general formula (I ″) characterized by reacting with a compound represented by [In the formula, R ¹ , R ² , R ³ , R ⁴ , X, Y ² , Z and m are the same as defined above. ] The manufacturing method of the benzyl hydrazone derivative represented by these. 7. A fungicide for agricultural and horticultural use, which comprises the benzylhydrazone derivative according to claim 1 as an active ingredient. 8. A fungicide for agricultural and horticultural use, comprising the benzylhydrazone derivative according to claim 2 as an active ingredient. 9. A fungicide for agricultural and horticultural use, which comprises the benzylhydrazone derivative according to claim 3 as an active ingredient. 10. A fungicide for agricultural and horticultural use containing the benzylhydrazone derivative according to claim 4 as an active ingredient.