JPWO2001010825A1 - Carbamate derivatives and agricultural and horticultural fungicides - Google Patents

Abstract

(57) [Abstract] A novel fungicide having high control effect against plant diseases, particularly wheat powdery mildew and cucumber gray mold, without adversely affecting crops, is provided. The fungicide has the general formula [I]: {wherein X represents a halogen atom, a _C1 - _C6 alkyl group, or the like; n represents 0 or an integer of 1 to 4; ^R1 represents a _C1 - _C6 alkyl group; ^R2 represents a hydrogen atom, a _C1 - _C6 alkyl group, or the like; ^R3 represents a hydrogen atom or a _C1 - _C6 alkyl group; G represents an oxygen atom, a sulfur atom, or the like; Y represents a hydrogen atom, a _C1 - _C10 alkyl group, a _C2 - _C10 alkenyl group, or the like; and Q represents a hydrogen atom, a _C1 - _C6 haloalkyl group, a phenyl group, or the like} and agricultural and horticultural fungicides containing them as active ingredients.

Description

Description: TECHNICAL FIELD The present invention relates to novel carbamate derivatives and agricultural and horticultural fungicides containing said derivatives as active ingredients.

BACKGROUND ART Although many carbamic acid derivatives have been reported, it has not been known that the carbamic acid derivative of the present invention, which has an oxime ether group on the phenyl group, has an excellent fungicidal activity.

An object of the present invention is to provide a novel carbamate derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

Disclosure of the Invention As a result of extensive research into the creation of a novel agricultural and horticultural fungicide, the inventors have discovered the
The carbamate derivative (hereinafter referred to as the compound of the present invention) is a novel compound not described in the literature.
and has been found to be a compound which exhibits a remarkable effect as an agricultural and horticultural fungicide.
The present invention has been completed. That is, the present invention provides: (1) a compound represented by general formula [I]{wherein X is a halogen atom, C₁~C₆Alkyl group, C₁~C₆alkoxy groups,
C₁~C₆haloalkyl group or C₁~C₆represents a haloalkoxy group, n is 0 or
represents an integer from 1 to 4; R¹is C₁~C₆represents an alkyl group, and R²is a hydrogen atom,
C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, C
₁~C₆Alkoxy group, C₁~C₆Alkoxy C₁~C₆Alkyl group, C₁~C
₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group, C₁~C₆Al
Kilcarbonyl C₁~C₆represents an alkyl group or an optionally substituted benzyl group,
R³is a hydrogen atom or C₁~C₆represents an alkyl group, and G is an oxygen atom, a sulfur atom, or
-NR⁴- group [R⁴is a hydrogen atom or C₁~C₆represents an alkyl group.
, Y is a hydrogen atom, C₁~C₁₀alkyl groups (which may be the same or different, one or more
, a halogen atom, a cyano group, a nitro group, a hydroxy group, C₃~C₆Cycloalkane
group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆alkylamino groups,
G-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Al
alkylsulfinyl group, carboxyl group, C₁~C₆Alkylcarbonyl group, C₁
~C₆Alkoxycarbonyl group, C₁~C₆Alkoxyimino group or C(O)N
R⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Al
C may be substituted with an alkyl group₂~C₁₀alkenyl groups (the groups are the same
or different one or more of a halogen atom, a cyano group, a nitro group, a hydroxy group,
C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C
₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello Aruki
group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or
is C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C
₁~C₆(representing an alkyl group), C₂~C₁₀Alkynyl group
(The group may be the same or different and may contain one or more of a halogen atom, a cyano group, a nitro group, a cyclohexyl ...
chloroalkyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁
~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Archi
Ruthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁
~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶teeth
The same or different hydrogen atoms or C₁~C₆may be substituted with an alkyl group
I), C₃~C₆Cycloalkyl groups (which may be the same or different, and may contain one or more halo groups)
aryl atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl
Group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino
Base, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁
~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkyl Carbo
Nyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where,
R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆(representing an alkyl group)
may be replaced), C₃~C₆Cycloalkenyl groups (the groups may be the same or different)
At least one halogen atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~
C₆Alkenyl group, hydroxy group, C₂~C₆Alkynyl group, amino group, mono C
₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Al
Koxy group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆
Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵
R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Alkyl
a phenacyl group (which may be substituted with one or more identical or different groups);
The above halogen atoms, C₁~C₆Alkyl group, C₁~C₆Alkoxy group, C₁
~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group or C₁~C₆Arco
aryl groups (which may be the same or different)
One or more halogen atoms, cyano groups, nitro groups, C₁~C₆Alkyl group, C₂
~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Al
Oxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Archi
C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C
₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR
⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Archi
a heteroaryl group (which may be substituted with the same or different alkyl groups);
one or more halogen atoms, cyano groups, nitro groups, C₁~C₆Alkyl group, C
₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆a
Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Al
alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~
C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)N
R⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Al
aryl-C₁~C₆Alkyl group (the group
The aryl may be the same or different and may be one or more of a halogen atom, a cyano group, a nitro group,
, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆alkynyl groups,
an optionally substituted phenoxy group, a hydroxy group, C₁~C₆Alkoxy group, amino
Noki, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C
₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Haloalkoki
C group, C₁~C₆Alkylcarbonyl group, C₁~C₆an alkoxycarbonyl group,
C₁~C₆Alkoxyimino C₁~C₆Alkyl group or C(O)NR⁵R⁶(child
So, R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Indicates an alkyl group
), aryl-C₂~C₆Alkenyl groups (aryl groups of the
are the same or different, and each represents one or more of a halogen atom, a cyano group, a nitro group, C₁~C
₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy
Group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di
-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello
alkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl
group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or
is C₁~C₆alkyl group) or heterocycle-C₁~C
₆alkyl groups, the heterocycles of which may be the same or different, containing one or more halogen atoms,
Cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~
C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C
₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Al
Chilthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C
₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶
are the same or different hydrogen atoms or C₁~C₆It may be substituted with an alkyl group
Q represents a hydrogen atom, a haloalkyl group, a cyano group, or C₁~C₆Alkyl
Group, C₃~C₆Cycloalkyl group, C₁~C₄Alkylthio group, C₁~C₄Al
alkylsulfinyl group, C₁~C₄Alkyl sulfonyl group or phenyl group (the group
is one or more halogen atoms, cyano groups, nitro groups, C₁~C₄Alkyl group, C
₂~C₄Alkenyl group, C₂~C₄Alkynyl group, hydroxy group, C₁~C₄a
Alkoxy group, C₁~C₄Haloalkyl group, C₁~C₄Haloalkoxy group, C₁~
C₄Alkylcarbonyl group or C₁~C₄The alkoxycarbonyl group is substituted
(2) carbamate derivatives represented by the formula (I) and (II) compounds containing these as active ingredients
It is an agricultural and horticultural fungicide.

The symbols and terms used in this specification will be explained below.

The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

The notation _C1 - _C10 etc. indicates that the number of carbon atoms in the following substituent is 1 to 1 in this case.
This indicates that the value is 0.

The _C1 to _C6 alkyl group refers to a linear or branched alkyl group, and examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1,1-dimethylpropyl, and 1,1-dimethylbutyl.

Examples of the C ₁ -C ₁₀ alkyl group include the above-mentioned C ₁ -C ₆ alkyl groups, heptyl, octyl, 1,1-diethylbutyl, nonyl, and decyl groups.

Examples of the _C3 - _C6 cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like groups.

The _C3 - _C6 cycloalkenyl group includes, for example, 1-cyclopenten-1-yl,
Examples include 2-cyclopenten-1-yl, 1-cyclohexen-1-yl, and 2-cyclohexen-1-yl groups.

The C ₁ -C ₆ haloalkyl group refers to a linear or branched alkyl group substituted with a halogen atom, and examples thereof include fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl, and pentafluoroethyl groups.

The _C2 - _C10 alkenyl group refers to a linear or branched alkenyl group, and examples thereof include vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 1-hexenyl, and 1-octenyl groups.

The _C2 to _C10 alkynyl group refers to a straight-chain or branched-chain alkynyl group, and examples thereof include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-1-pentynyl, and 3-methyl-1-pentynyl groups.

The C ₁ -C ₆ alkoxy group refers to an alkyloxy group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include methoxy, ethoxy, n-propoxy, isopropoxy,
Examples of such groups include n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, and n-hexyloxy.

The C ₁ -C ₆ haloalkoxy group refers to a haloalkyloxy group in which the haloalkyl moiety has the above-mentioned meaning, and examples thereof include fluoromethoxy, difluoromethoxy, trifluoromethoxy, pentafluoroethoxy and the like groups.

The C ₁ -C ₆ alkoxyimino group refers to an alkoxyimino group in which the alkoxy moiety has the above-mentioned meaning, and examples thereof include groups such as methoxyimino.

The C ₁ -C ₆ alkoxyimino C ₁ -C ₆ alkyl group refers to an alkoxyiminoalkyl group in which the alkoxy and alkyl portions have the same meanings as above, and examples thereof include 1
-methoxyiminoethyl and the like groups can be mentioned.

The C ₁ -C ₆ alkylcarbonyl group refers to an alkylcarbonyl group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include acetyl, propionyl, butyryl, isobutyryl, pivaloyl, and hexanoyl groups.

The C ₁ -C ₆ alkoxycarbonyl group refers to an alkoxycarbonyl group in which the alkoxy moiety has the above-mentioned meaning, and examples thereof include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, and hexyloxycarbonyl groups.

The _C1 - _C6 alkylcarbonyl _C1 - _C6 alkyl group refers to an alkylcarbonylalkyl group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include a 2-oxopropyl group, a 3-oxobutyl group, a 3-oxopentyl group, and a 3,3-dimethyl-2-oxobutyl group.

The aryl group represents an aromatic hydrocarbon group, such as phenyl, 1-naphthyl, 2-
-naphthyl and the like groups are also included.

The heterocyclic-C ₁ -C ₆ alkyl group is a group in which the alkyl portion is —CH ₂ —, —CH ₂ C
_H2 -,- _{CH2CH2CH2 -} ,-CH(Me ₎ -,-C(Me) ₂ -,-C
H(Et)-, etc., wherein the heterocyclic moiety has 2 to 9 carbon atoms, 0 to 3 nitrogen atoms,
represents a 3- to 10-membered ring composed of 0 to 3 oxygen atoms and 0 to 3 sulfur atoms, and examples thereof include pyrrolyl, furyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl,
It refers to groups such as imidazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzofuryl, benzothienyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, quinolyl, isoquinolyl, morpholino, oxiranyl, dioxacyclopentyl, and the like.

The heteroaryl group refers to a 5- to 10-membered heteroaromatic ring group composed of 2 to 9 carbon atoms, 0 to 3 nitrogen atoms, 0 to 3 oxygen atoms, and 0 to 3 sulfur atoms, and examples thereof include pyrrolyl, furyl, thienyl, pyrazolyl, isoxazolyl, isothiazolyl, imidazolyl, oxazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzofuryl, benzothienyl,
Examples include heterocycles such as benzimidazolyl, benzoxazolyl, benzothiazolyl, quinolyl, and isoquinolyl.

The C ₁ -C ₆ alkoxy C ₁ -C ₆ alkyl group refers to a group in which the alkyl and alkoxy portions have the above-mentioned meanings, such as methoxymethyl, ethoxymethyl,
Examples of groups that can be mentioned include isopropoxymethyl, pentyloxymethyl, methoxyethyl, butoxyethyl, and the like.

The mono C ₁ -C ₆ alkylamino group refers to a group in which the alkyl portion has the above-mentioned meaning, and examples thereof include methylamino, ethylamino, isopropylamino, butylamino, te
Examples include groups such as rt-butylamino.

The di-C ₁ -C ₆ alkylamino group refers to a group having the above-mentioned meaning, in which the alkyl portions may be the same or different, and examples thereof include dimethylamino, diethylamino, methylethylamino, methylisopropylamino, dihexylamino, and the like groups.

The C ₁ -C ₆ alkylthio group refers to a group in which the alkyl moiety has the above-mentioned meaning,
Examples of such groups include methylthio, ethylthio, isopropylthio, butylthio, and hexylthio.

The C ₁ -C ₆ alkylsulfinyl group refers to a group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include methylsulfinyl, ethylsulfinyl, isopropylsulfinyl, butylsulfinyl, and hexylsulfinyl groups.

The C ₁ -C ₆ alkylsulfonyl group refers to a group in which the alkyl moiety has the above-mentioned meaning, and examples thereof include methylsulfonyl, ethylsulfonyl, isopropylsulfonyl, butylsulfonyl, hexylsulfonyl and the like groups.

The aryl C ₁ -C ₆ alkyl group is one in which the aryl moiety has the above-mentioned meaning and the alkyl moiety is -CH ₂ -, -CH ₂ CH ₂ -, -CH ₂ CH ₂ CH ₂ -, -CH(M
e) represents a group such as -, -C(Me) ₂ -, -CH(Et)-, etc.;

The aryl C ₁ -C ₆ alkenyl group is an aryl group having the above-mentioned meaning and an alkenyl group selected from -CH═CH-, -CH═CHCH ₂ -, -C(Me)═CH-,
It represents a group such as -CH(Et)=CH-, -C(Me)=CHCH ₂ -, etc.

The heteroaryl C ₁ -C ₆ alkyl group is a group in which the heteroaryl moiety has the same meaning as above and the alkyl moiety is -CH ₂ -, -CH ₂ CH ₂ -, or -CH ₂ CH ₂ CH ₂ -.
, —CH(Me)—, —(Me) ₂ —, —CH(Et)—, and the like.

BEST MODE FOR CARRYING OUT THE INVENTION Specific examples of the compound of the present invention represented by the general formula [I] are shown in Tables 1 to 13. However, the compound of the present invention is not limited to these compounds.
The compound numbers will be referred to in the following description.

The symbols in the table have the following meanings: Me represents a methyl group, Et represents an ethyl group, Pr represents an n-propyl group, Pr-i represents an isopropyl group, Bu represents an n-butyl group, Bu-i represents an isobutyl group, Bu-s represents a sec-butyl group, Bu-t represents a tert-butyl group, Hex represents an n-hexyl group, Pr-c represents a cyclopropyl group, Pen-c represents a cyclopentyl group, Hex-c represents a cyclohexyl group, and Ph represents a phenyl group. Furthermore, for example, Ph(4-Cl) represents a 4-chlorophenyl group.

The compounds of the present invention represented by the general formula [I] have one or two to three double bonds related to E/Z isomers in the molecule, and such compounds exist as E/Z isomer mixtures. The compounds of the present invention also include pure individual E and Z isomers and mixtures thereof. The following compounds are geometric isomers related to the double bond of the oxime moiety (A-80 and A-206, A-84 and A-207, A-85 and A-206, A-86 and A-207, A-87 and A-207, A-88 and A-208).
8, A-86 and A-209, A-286 and A-448).

Representative methods for producing the carbamate derivatives of the present invention, represented by general formula [I], are exemplified below. Since the novel compounds of general formula [I] have a C=N double bond, they may be produced as an E/Z isomer mixture during production. This isomer mixture can be isolated into individual components by purification methods such as crystallization or column chromatography. Both the individual isomers and mixtures thereof are encompassed by the present invention.

<Manufacturing method 1> (wherein G, R ¹ , R ² , R ³ , Q, X, Y and n are as defined above, respectively.) Compound [I] of the present invention can be produced by reacting compound [II] with compound [III] in an inert solvent (see, for example, Jikken Kagaku Koza, 4th Edition, Vol. 20,
Vol. 349-355 (edited by the Chemical Society of Japan). The starting compound [III] used in this production method may form a salt with hydrochloric acid, sulfuric acid, etc. Compound [II]
I] can be produced according to known methods (for example, Experimental Chemistry Lectures, 4th Edition,
20, pp. 342-349).

The amount of the starting compound used in this reaction is the same as that of the compound [II].
The amount of the inert solvent that can be used in this production method is selected appropriately from the range of 1 to 50 equivalents, preferably 1 to 10 equivalents.
Examples of inert solvents that can be used include alcohols such as propanol and isopropanol, ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane and diethylene glycol dimethyl ether, aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene and toluene, and water. These inert solvents can be used alone or in combination.

In this production method, acids such as hydrochloric acid and acetic acid, or bases such as sodium acetate, sodium carbonate, and sodium bicarbonate can be used in combination.
The amount of the compound [II] used may be appropriately selected from the range of 0.001 to 50 equivalents, preferably 0.01 to 50 equivalents.
The reaction temperature is from −10° C. to the boiling point of the inert solvent used.
The reaction temperature is preferably from 0° C. to the boiling point of the inert solvent used. The reaction time varies depending on the reaction temperature, reaction amount, etc., but may generally be selected from the range of 1 to 48 hours.
After the reaction is completed, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization or the like.

<Manufacturing method 2> (wherein G, R ¹ , R ² , R ³ , X and n are as defined above,
Q' represents a cyano group or a nitro group, and A represents a _C1 - _C10 alkyl group. The compound [I-a] of the present invention can be produced by reacting the compound [IV] with the nitrite ester [V] in the presence of a base (see, for example, Organic Syntheses, Vol. 6, p. 199 (198
The amount of the starting compound used in this reaction may be appropriately selected from the range of 1 to 50 equivalents of compound [V] relative to compound [IV], and preferably 1 to 50 equivalents.
10 equivalents.

Examples of the base to be used in this production method include alkali metal alcoholates such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide;
Inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, etc. can be used. The amount of the base used is 0.5 times the amount of compound [IV].
The amount may be appropriately selected from the range of 1 to 50 equivalents, preferably 1 to 10 equivalents.

The inert solvent that can be used in this production method is any solvent that does not inhibit the progress of this production method, and examples thereof include ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, 1,2-dimethoxyethane, and diethylene glycol dimethyl ether; dichloromethane; chloroform; carbon tetrachloride;
Halogenated hydrocarbons such as tetrachloroethane, aromatic hydrocarbons such as benzene, chlorobenzene, and toluene, and alcohols such as methanol, ethanol, propanol, and isopropanol can be used, and these inert solvents can be used alone or in combination.

The reaction temperature is from -70°C to the boiling point of the inert solvent used, preferably from -20°C
° C. to the boiling point of the inert solvent used. The reaction time varies depending on the reaction temperature, reaction amount, etc., but may generally be selected within the range of 1 to 100 hours, preferably 12 to 75 hours.

After the reaction is completed, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization or the like.

<Manufacturing method 3> (In the formula, G, R ¹ , R ² , R ³ , X, Q, and n are the same as defined above, Y′ is the same as defined above for Y other than hydrogen, and L is a leaving group and represents a halogen atom or a sulfonate ester such as tosyloxy or mesyloxy.)
The compound [I-e] of the present invention can be prepared by reacting the compound [I-b] of the present invention with the compound [VI] in the presence of a base.

The amount of the starting compound used in this reaction is the same as that of the compound [I-b].
VI] may be appropriately selected from the range of 1 to 50 equivalents, preferably 1 to 5 equivalents.

In this production method, an inert solvent can be used in some cases. The inert solvent may be any solvent that does not inhibit the progress of this reaction, and examples thereof include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether; esters such as ethyl acetate and methyl acetate;
Examples of inert solvents that can be used include halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride; aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene, and toluene; nitriles such as acetonitrile; N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone, and dimethyl sulfoxide. These inert solvents can be used alone or in combination.

The base to be used may be, for example, an alkali metal hydride such as sodium hydride,
Alkali metal alcoholates such as potassium tert-butoxide, sodium carbonate,
Inorganic salts such as potassium carbonate can be used. The amount of base used is determined by the compound [
I-b], it may be appropriately selected from the range of 1 to 50 equivalents,
10 equivalents.

The reaction temperature is from -70°C to the boiling point of the inert solvent used, preferably 0°C.
The reaction time varies depending on the reaction temperature, reaction amount, etc., but is generally selected from the range of 1 hour to 72 hours. After the reaction is completed, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization, etc.

<Manufacturing method 4> {wherein G, Q, R ¹ , R ² , R ³ , X, Y and n are as defined above, and L′ represents a halogen atom.} Compound [VII] can be halogenated by a known method to obtain compound [VIII].
] can be produced (for example, see Experimental Chemistry Lectures, 4th Edition, Vol. 19, pp. 416-4
82 (edited by the Chemical Society of Japan) (Step 4.1). Compound [VIII] is reacted with compound [IX] in the presence of a base in an inert solvent to obtain the compound of the present invention [
Furthermore, the compound [I-d] of the present invention can be prepared by reacting the compound [VIII] with an alkali metal cyanate and the compound [X] in an inert solvent (see, for example, The Journal of Chemical Science, Vol. 87, No. 5, p. 486 (1966)) (Step 4.3).

Examples of halogenating agents that can be used in step 4.1 of this production method include N-bromosuccinimide, N-chlorosuccinimide, and trichloroisocyanuric acid. The amount of the halogenating agent used may be appropriately selected from the range of 0.5 to 10 equivalents relative to compound [VII], and preferably 1 to 3 equivalents. In this step, a catalyst such as azobisisobutyronitrile or benzoyl peroxide may be used in an amount that can be appropriately selected from the range of 0.001 to 10 equivalents relative to compound [VII], and preferably 0.001 to 1 equivalent.

Any inert solvent may be used as long as it does not inhibit the progress of Step 4.1. For example, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, and aromatic hydrocarbons such as benzene and chlorobenzene can be used.

The reaction temperature is from 0°C to the boiling point of the inert solvent used. The reaction time varies depending on the reaction temperature,
Although the reaction time varies depending on the reaction amount, etc., it may generally be selected from the range of several minutes to 48 hours. After completion of the reaction, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization, etc.

The amount of the starting compound [IX] used in step 4.2 of this production method is
III], and preferably 1 to 50 equivalents.
10 equivalents.

The base that can be used includes inorganic salts such as sodium carbonate, potassium carbonate, sodium bicarbonate, etc., and alkali metal hydrides such as sodium hydride, etc. The amount of the base used can be appropriately selected from the range of 0.5 to 100 equivalents relative to compound [VIII], and is preferably 1 to 10 equivalents.

The inert solvent that can be used may be any solvent that does not inhibit the progress of Step 4.2, and examples thereof include ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc.; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, diglyme, etc.; esters such as ethyl acetate, methyl acetate, etc.; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc.; aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene, toluene, etc.; nitriles such as acetonitrile, etc.; alcohols such as methanol, ethanol, butanol, etc.; N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-propanol, etc.;
These inert solvents can be used alone or in combination.

The reaction temperature is from -70°C to the boiling point of the inert solvent used, preferably from -10
°C to the boiling point of the inert solvent used. The reaction time varies depending on the reaction temperature, reaction amount, etc., but can generally be selected from the range of several minutes to 48 hours. After completion of the reaction, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization, etc.

Examples of the alkali metal cyanate salt that can be used in step 4.3 of this production method include potassium cyanate and sodium cyanate. The amount of the metal cyanate salt to be used may be appropriately selected from the range of 1 to 50 equivalents relative to compound [VIII], preferably 1 to 10 equivalents. Compound [X] is used in the reaction of compound [VIII] with a hydroxy group of 1 to 50 equivalents.
The inert solvent may be appropriately selected from the range of 1 to 100 equivalents relative to the amount of the methyl group, preferably 1 to 20 equivalents. Any inert solvent may be used as long as it does not inhibit the progress of Step 4.3, and examples thereof include ketones such as acetone, methyl ethyl ketone, cyclohexanone, etc., ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme, diglyme, etc., esters such as ethyl acetate, methyl acetate, etc., halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, etc., aromatic hydrocarbons such as benzene, chlorobenzene, nitrobenzene, toluene, etc., nitriles such as acetonitrile, alcohols such as methanol, ethanol, butanol, N,N-dimethylformamide, N,N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone, dimethyl sulfoxide, etc., and these inert solvents may be used alone or in combination.

The reaction temperature is from 0°C to the boiling point of the inert solvent used, and the reaction time is
Although the reaction time varies depending on the reaction amount, etc., it is generally selected from the range of 1 hour to 48 hours. After completion of the reaction, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization, etc.

<Manufacturing method 5>{In the formula, G, R¹and R³have the same meanings as above, and X¹, X², X
³and X⁴are a hydrogen atom, a halogen atom, and C₁~C₆Alkyl group, C₁
~C₆Alkoxy group, C₁~C₆haloalkyl group or C₁~C₆Haloalkoxy
group, Q" represents a hydrogen atom, a haloalkyl group, C₁~C₆Alkyl group, C₃~C
₆A cycloalkyl group or a phenyl group (which may contain one or more halogen atoms, sialin
No group, nitro group, C₁~C₄Alkyl group, C₂~C₄Alkenyl group, C₂~C₄
Alkynyl group, hydroxy group, C₁~C₄Alkoxy group, C₁~C₄Hello Aruki
group, C₁~C₄Haloalkoxy group, C₁~C₄Alkylcarbonyl group, C₁~
C₄(The alkoxycarbonyl group may be substituted.)} Compound [XVIII] is reacted with sodium nitrite in the presence of hydrochloric acid according to a known method.
The compound is then diazotized with sodium acetate and copper sulfate.
The compound [If] of the present invention can be produced by reacting the compound [XIX] with
(e.g. Organic Syntheses
5, 139 (1973).

The amount of the starting compound used in this reaction may be appropriately selected from the range of 1 to 50 equivalents of compound [XIX] relative to compound [XVIII], and preferably 1 to 5
It is equivalent.

The solvent that can be used in this production method is not particularly limited as long as it does not inhibit the progress of the reaction. Examples of the solvent include ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, dimethoxyethane, and diethylene glycol dimethyl ether, esters such as ethyl acetate and methyl acetate, halogenated hydrocarbons such as dichloromethane, chloroform, and carbon tetrachloride, benzene, chlorobenzene,
Aromatic hydrocarbons such as nitrobenzene and toluene, organic acids such as acetic acid and trifluoroacetic acid, water, etc. can be used, and these solvents can be used alone or in combination.

In the diazotization step 1) of this production method, a strong acid such as sulfuric acid, hydrofluoroboric acid, hydrobromic acid, or trifluoroacetic acid can be used instead of the hydrochloric acid. The amount used can be appropriately selected from the range of 1 to 50 equivalents relative to compound [XVIII], preferably 2 to 4 equivalents. In addition, a nitrite ester such as isoamyl nitrite or methyl nitrite can be used instead of the sodium nitrite. The amount used can be appropriately selected from the range of 1 to 50 equivalents relative to compound [XVIII], preferably 1 to 2 equivalents. The reaction temperature is in the range of -20°C to 30°C.
The reaction temperature is preferably in the range of -5°C to 5°C. The reaction time varies depending on the reaction temperature, reaction amount, etc., but is generally selected from the range of 30 minutes to 2 hours. As the copper compound used in step 2) of the coupling of this reaction, copper salts such as copper chloride (I) and copper acetate (II) can be used instead of the copper sulfate. The amount used is determined by the ratio of the compound [X
The amount of sodium acetate used may be appropriately selected from the range of 0.02 to 2 equivalents relative to the amount of compound [X].
VIII] may be appropriately selected from the range of 1 to 50 equivalents, and preferably 4
The reaction temperature is in the range of -20°C to 30°C, preferably -5
The reaction time varies depending on the reaction temperature, reaction amount, etc.
Generally, the reaction time may be selected from the range of 30 minutes to 2 hours. After completion of the reaction, the target product is isolated from the reaction system by a conventional method and, if necessary, purified by column chromatography, recrystallization or the like.

Compound [II], which is an intermediate for compound [I] of the present invention, can be prepared by the following known methods, but is not limited to those shown here.

{wherein L', G, Q, ^R1 , ^R2 , ^R3 , X and n are as defined above.} Compound [XII] can be produced by halogenating compound [XI] (see, for example, Jikken Kagaku Koza, 4th Edition, Vol. 19, pp. 416-482 (
(See, for example, "The Chemical Society of Japan") (Step A-1). Furthermore, intermediate [II] can be produced by reacting compound [XII] with compound [IX] in the presence of a base (e.g., inorganic salts such as sodium carbonate, potassium carbonate, sodium bicarbonate, etc., alkali metal hydrides such as sodium hydride, etc.) (Step A-2). Furthermore, intermediate [II-a] can be produced by reacting compound [XII] with alkali metal cyanate salts and compound [X] in an inert solvent (see, for example, "The Chemical Society of Japan," Vol. 87, No. 5, p. 486 (1966)") (Step A-3).

The compounds [II] and [IV-a], which are intermediates of the compound [I] of the present invention, can be prepared by the following known methods, but are not limited to those shown here.

{wherein G, Q, ^R1 , ^R2 , ^R3 , X, L' and n are as defined above, and T represents a _C1 - _C6 alkyl group.} Compound [XIV] can be produced by halogenating compound [XIII] (see, for example, Jikken Kagaku Koza, 4th Edition, Vol. 19, pp. 416-482 (edited by the Chemical Society of Japan)) (Step B-1). Compound [XIV] and compound [X] can be reacted with an alkali metal cyanate salt to produce compound [XV] (see, for example, Nihon Kagaku Zasshi, Vol. 87, No. 5, p. 486 (1966)) (Step B-2). Alternatively, compound [XIV] can be reacted with sodium carbonate, potassium carbonate,
Compound [IX] is reacted with compound [IX] in the presence of a base such as an inorganic salt such as sodium bicarbonate or an alkali metal hydride such as sodium hydride to give compound [XV]
Compound [XVI] can be produced by reducing compound [XV] by a conventional method (see, for example, Jikken Kagaku Koza (Experimental Chemistry Course), 4th Edition, Vol. 26, pp. 159-266 (edited by the Chemical Society of Japan)) (Step B-4).
Compound [II-b] can be prepared by oxidizing compound [XVI] by a conventional method (see, for example, Experimental Chemistry Lectures, 4th Edition, Vol. 21, pp. 2-23 (edited by the Chemical Society of Japan) (Step B-5)). Compound [XVI] can be halogenated by a conventional method to prepare compound [XVII] (see, for example, 4th Edition, Experimental Chemistry Lectures, pp. 2-23 (edited by the Chemical Society of Japan)).
See Jikken Kagaku Koza, Vol. 19, pp. 416-482 (edited by the Chemical Society of Japan) (Step B-6).

Compound [XVII] is cyanated by a conventional method to give compound [IV-
a] can be produced (for example, see Experimental Chemistry Lectures, 4th Edition, Vol. 20, pp. 437-439).
See page 462 (edited by the Chemical Society of Japan) (Step B-7).

Compound [VII], which is an intermediate for compound [I] of the present invention, can be prepared by the following known methods, but is not limited to the methods shown here.

(wherein R ³ , Q, X, Y and n are as defined above). The compound [XI] is reacted with the compound [III] to obtain the compound [V] of the present invention.
II] can be produced (for example, see Experimental Chemistry Lectures, 4th Edition, Vol. 20, p. 349
See pages 1-355 (edited by the Chemical Society of Japan). The raw material compounds used in this production method [
III] may form a salt with hydrochloric acid, sulfuric acid, or the like.

The compound [XVIII], which is an intermediate for the compound [I] of the present invention, can be prepared by the following known methods, but is not limited to the methods shown here.

{wherein G, R ¹ , R ³ , L′, X ¹ , X ² , X ³ and X ⁴ are as defined above.} Intermediate [XXI] can be produced by reacting compound [XX] with an alkali metal cyanate and compound [X] in an inert solvent (see, for example, Nippon Kagaku Zasshi, Vol. 87, No. 5, p. 486 (1966)) (Step C
Intermediate [XXII] can be produced by nitrating compound [XXI] with nitric acid, acetyl nitrate, sodium nitrate, or the like (see, for example, "Experimental Chemistry Lectures, 4th Edition," Vol. 20, pp. 394-399 (edited by the Chemical Society of Japan)) (Step C-2). Compound [XXII] can be reduced by a conventional method to produce intermediate [XXII].
XVIII] can be produced (for example, Experimental Chemistry Lectures, 4th Edition, Vol. 26,
See pages 159-266 (edited by the Chemical Society of Japan) (Step C-3).

EXAMPLES Next, the production method, formulation method and use of the compound of the present invention will be specifically explained with reference to examples.

Other abbreviations used in the text have the following meanings:

¹ H-NMR: proton nuclear magnetic resonance CDCl ₃ : deuterated chloroform TMS: tetramethylsilane s: singlet d: doublet t: triplet q: qu
artet quint: quintet m: multiplet br: broad dd: dou
ble double.

<Production Example 1> 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-
Preparation of hydroxyiminoacetonitrile (Compound No. A-2) 0.15 g of sodium hydroxide and 0.60 g of methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate were added to 5 ml of ethanol, and 0.40 g of t-butyl nitrite was added to this mixture at room temperature and stirred for 72 hours. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (
The product was purified using Wakogel C-200 (elution solvent: hexane/ethyl acetate = 3/1) to obtain 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]
0.46 g of 2-hydroxyiminoacetonitrile was obtained as a colorless viscous liquid.
¹ H-NMR: ( _CDCl3 /TMS, δ(ppm)) 3.72 (s, 3H); 4.48 (d, 2H); 5.43 (br, 1H); 7.
43-8.21 (m, 3H); 10.51, 11.15 (br, 1H).

<Production Example 2> 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-
Preparation of methoxyiminoacetonitrile (Compound No. A-3) 2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2
0.36 g of hydroxyiminoacetonitrile and 0.54 g of a 28% sodium methylate methanol solution were added to 5 ml of methanol, 0.49 g of methyl iodide was added, and the mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated under reduced pressure, the solvent was distilled off, water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Wako Gel C-
200, elution solvent: hexane/ethyl acetate = 4/1 to 5/1),
2-[4-chloro-3-(methoxycarbonylaminomethyl)phenyl]-2-
0.18 g of methoxyiminoacetonitrile was obtained as colorless crystals (melting point 104-107°C).
¹ H-NMR: (CDCl ₃ /TMS, δ(ppm)) 3.71(s, 3H); 4.22(s, 3H); 4.48(d, 2H); 5.2
3 (br, 1H); 7.43-8.05 (m, 3H).

<Production Example 3> Production of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate (Compound No. A-45) 5.0 g of methyl N-(2-chloro-5-acetylbenzyl)carbamate was dissolved in 10 ml of ethanol, and 1.5 g of hydroxyamine hydrochloride and 3 g of sodium acetate were added.
0 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate and 5.2 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate were added to a reaction mixture containing 5 ml of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate and heated under reflux for 4 hours. After the reaction was completed, water was added, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crystals were washed with hexane, and 5.2 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate was obtained as colorless crystals (melting point 124
-127°C). ^1H -NMR: ( _CDCl3 /TMS, δ (ppm)) 2.25 (s, 3H); 3.70 (s, 3H); 4.46 (d, 2H); 5.3
1 (br, 1H); 7.27-7.63 (m, 3H).

<Production Example 4> Production of methyl N-[3-(1-methoxyiminoethyl)benzyl]carbamate (Compound No. A-40) 0.40 g of methyl N-(3-acetylbenzyl)carbamate was dissolved in 10 ml of ethanol.
The resulting solution was dissolved in 1 ml of methyl methacrylate, and 5 ml of a solution of 0.36 g of methoxyamine hydrochloride and 0.54 g of sodium acetate was added thereto, followed by heating under reflux for 8 hours. After the reaction was completed, water was added, the mixture was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crystals were washed with hexane to obtain 0.40 g of methyl N-[3-(1-methoxyiminoethyl)benzyl]carbamate as a pale yellow oil. ¹ H-NMR: (CDCl ₃ /TMS, δ(ppm)) 2.22 (s, 3H); 3.69 (s, 3H); 3.99 (s, 3H); 4.3
7 (d, 2H); 5.12 (br, 1H); 7.27-7.56 (m, 4H).

<Production Example 5> N-{2-chloro-5-[1-(4-fluorobenzyloxyimino)ethyl]
Preparation of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate (Compound No. A-83) 0.70 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate was dissolved in 10 ml of N,N-dimethylformamide, and 0.13 g of 60% sodium hydride was added under ice cooling and stirred for 1 hour. 0.57 g of 4-fluorobenzyl bromide was dissolved in 2 ml of N,N-dimethylformamide,
The mixture was added dropwise to the reaction mixture under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction mixture was poured into water, extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-200, elution solvent: hexane/ethyl acetate = 5/1).
) and purified by HPLC to obtain 0.75 g of methyl N-{2-chloro-5-[1-(4-fluorobenzyloxyimino)ethyl]benzyl}carbamate (mp 101-110°C).
^1H -NMR: ( _CDCl3 /TMS, δ(ppm)) 2.22(s, 3H); 3.69(s, 3H); 4.45(d, 2H); 5.1
0 (br, 1H); 5.18 (s, 2H); 7.02-7.65 (m, 7H).

<Production Example 6> Production of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate (Compound No. A-45)
The resulting solution was dissolved in 33 g of % hydrochloric acid and stirred at room temperature for 1 hour. To this solution, 7 ml of an aqueous solution of 3.8 g of sodium nitrite was added dropwise at 0 to 5° C. under stirring. The resulting diazonium salt was dissolved in 21.7 g of sodium acetate, 2.6 g of copper sulfate, and 5.9 g of acetaldoxime.
g of water/ethyl acetate/toluene (80 ml/40 ml/40 ml) mixed solvent.
The mixture was added dropwise over 15 minutes with vigorous stirring at 5°C, and then stirred at room temperature for a further 2 hours.
The reaction mixture was acidified with hydrochloric acid, extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting crude crystals were washed with a mixed solvent of ether and ethyl acetate to give 2.8 g of methyl N-[2-chloro-5-(1-hydroxyiminoethyl)benzyl]carbamate as colorless crystals (melting point 124-122).
7°C). ¹ H-NMR: (CDCl ₃ /TMS, δ (ppm)) 2.25 (s, 3H); 3.70 (s, 3H); 4.46 (d, 2H); 5.3
1 (br, 1H); 7.27-7.63 (m, 3H).

<Production Example 7> Production of methyl N-{2-methyl-5-[1-(6-methylpyridin-2-ylmethoxy)iminoethyl]benzyl}carbamate (Compound No. A-434) 0.43 g of methyl N-[2-methyl-5-(1-hydroxyiminoethyl)benzyl]carbamate was dissolved in 15 ml of N,N-dimethylformamide, 0.75 g of potassium carbonate and 0.32 g of 2-chloro-6-methylpyridine hydrochloride were added, and the mixture was heated and stirred at 90 to 100°C for 8 hours. After completion of the reaction, the reaction solution was poured into water, and
The mixture was extracted with ethyl acetate, washed with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-
200, elution solvent: hexane/ethyl acetate = 4/1) and N-{2
0.30 g of methyl 5-[1-(6-methylpyridin-2-ylmethoxy)iminoethyl]benzyl}carbamate (m.p. 72-75°C) was obtained as pale yellow crystals. ¹ H-NMR: (CDCl ₃ /TMS, δ(ppm)) 2.30 (s, 3H); 2.32 (s, 3H); 2.56 (s, 3H); 3.6
9 (s, 3H); 4.35 (d, 2H); 4.94 (br, 1H); 5.33 (
s, 2H); 7.04-7.59 (m, 6H).

Next, ¹ H-NMR (CDCl ₃ /TMS) of some examples of the compounds of the present invention will be described.
, δ (ppm)) data are shown in Tables 14 to 20.

Next, examples of preparation of synthetic intermediates for the compounds of the present invention are shown as reference examples.

Reference Example 1: Preparation of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate 40.4 g of methyl 4-chloro-3-methylbenzoate, 39 g of N-bromosuccinimide, and 1 g of azobisisobutyronitrile were added to 300 ml of carbon tetrachloride and heated under reflux for 4 hours. After the reaction was completed, the mixture was cooled to room temperature, insoluble matter was filtered off, and the filtrate was concentrated. The obtained crude crystals were washed with hexane to obtain 34.3 g of methyl 3-bromomethyl-4-chlorobenzoate as white crystals.

16.0 g of the obtained methyl 3-bromomethyl-4-chlorobenzoate, 15.0 g of potassium cyanate, and 35 ml of methanol were dissolved in 20 ml of N,N-dimethylformamide.
The reaction mixture was added to 0 ml of ethyl acetate and stirred at 90°C for 4 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with isopropanol to obtain 25.2 g of methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate as white crystals.
¹ H-NMR: ( _CDCl3 /TMS, δ (ppm)) 3.70 (s, 3H); 3.90 (s, 3H); 4.48 (d, 2H); 5.2
9 (br, 1H); 7.43 (d, 1H); 7.89 (dd, 1H); 8.05
(s, 1H).

<Reference Example 2> Method for producing methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate Methyl 4-chloro-3-(methoxycarbonylaminomethyl)benzoate 10.3
g was dissolved in 80 ml of anhydrous tetrahydrofuran, and 100 ml of diisobutylaluminum hydride (0.95 M hexane solution) was added under a nitrogen atmosphere and the mixture was heated at -50°C to -30°C.
After the completion of the dropwise addition, the mixture was stirred at room temperature for 16 hours.
Dilute hydrochloric acid was added dropwise at °C, water was added, the mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (Wakogel C-200, elution solvent: hexane/ethyl acetate = 1/1) to obtain 6.5 g of methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate as white crystals. ¹ H-NMR: (CDCl ₃ /TMS, δ (ppm)) 2.20 (br, 1H); 3.67 (s, 3H); 4.43 (d, 2H); 4.
65 (s, 2H); 5.26 (br, 1H); 7.2 1-7.37 (m, 3H
).

<Reference Example 3> Method for producing methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate Methyl N-(2-chloro-5-hydroxymethylbenzyl)carbamate 6.2
[0049] 2.7 g of the product was dissolved in 50 ml of ethylene glycol dimethyl ether, and 2.7 g of phosphorus tribromide was added dropwise to the solution at -20°C, followed by stirring at room temperature for 1 hour. After the reaction was completed, water was added to the reaction solution, which was then extracted with ethyl acetate and washed with an aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.1 g of methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate as white crystals.
¹ H-NMR: ( _CDCl3 /TMS, δ (ppm)) 3.70 (s, 3H); 4.37 (d, 2H); 4.49 (s, 2H); 5.2
0 (br, 1H); 7.25-7.40 (m, 3H).

Reference Example 4: Preparation of methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate 2.3 g of methyl N-(5-bromomethyl-2-chlorobenzyl)carbamate obtained in Reference Example 3 was dissolved in 20 ml of N,N-dimethylformamide, and 0.43 g of sodium cyanide was added at 0°C. After stirring at 0°C for 1 hour and then at room temperature for 4 hours, water was added to the reaction mixture, which was then extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting crude crystals were washed with hexane to obtain 1.3 g of methyl N-(2-chloro-5-cyanomethylbenzyl)carbamate as white crystals. ¹ H-NMR: (CDCl ₃ /TMS, δ(ppm)) 3.70 (s, 3H); 3.73 (s, 2H); 4.44 (d, 2H); 5.2
1 (br, 1H); 7.24-7.40 (m, 3H).

Reference Example 5: Preparation of methyl N-(2-chloro-5-acetylbenzyl)carbamate 25.0 g of 4-chloro-3-methylacetophenone, 26.6 g of N-bromosuccinimide, and a catalyst amount of azobisisobutyronitrile were added to 150 ml of carbon tetrachloride, and the mixture was refluxed for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue, 18.0 g of potassium cyanate, and 38% methanol were added to the mixture.
The resulting solution was added to 150 ml of N,N-dimethylformamide and stirred at 90°C for 4 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (Wakogel C-200, elution solvent: hexane/ethyl acetate), washed with isopropyl ether, and purified to give N-(2-chloro-5-
6.8 g of methyl (acetylbenzyl)carbamate was obtained as colorless crystals. ¹ H-NMR: (CDCl ₃ /TMS, δ (ppm)) 2.59 (s, 3H); 3.70 (s, 3H); 4.50 (d, 2H); 5.3
1 (br, 1H); 7.46 (d, 1H); 7.81 (dd, 1H); 7.97
(s, 1H).

Reference Example 6: Preparation of methyl N-(2-chloro-5-acetylbenzyl)carbamate. 25.0 g of 4-chloro-3-methylacetophenone and 13.9 g of trichloroisocyanuric acid were suspended in 150 ml of chlorobenzene. A catalytic amount of azobisisobutyronitrile was added, and the mixture was heated and stirred at 85-90°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature, and insoluble matter was filtered off. The filtrate was washed with aqueous sodium hydroxide and then with water, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue, 12.2 g of potassium cyanate, and 14.4 g of methanol were added to 150 ml of N,N-dimethylformamide, and the mixture was heated and stirred at 90°C for 4 hours. After the reaction was completed, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (Wakogel C-200, elution solvent: hexane/ethyl acetate = 3/1). The obtained crystals were washed with isopropyl ether to obtain 6.0 g of methyl N-(2-chloro-5-acetylbenzyl)carbamate as colorless crystals.
¹ H-NMR: ( _CDCl3 /TMS, δ (ppm)) 2.59 (s, 3H); 3.70 (s, 3H); 4.50 (d, 2H); 5.3
1 (br, 1H); 7.46 (d, 1H); 7.81 (dd, 1H); 7.97
(s, 1H).

The agricultural and horticultural fungicide of the present invention contains the carbamate derivative represented by general formula [I] as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate formulation depending on the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and surfactants and other additives are added as needed, and the active ingredient can be used in the form of a powder, wettable powder, emulsifiable concentrate, granules, or the like. The blending ratio of the active ingredient is appropriately selected as needed, but when used as a powder or granule, it is 0.1
In the case of emulsifiable concentrates and wettable powders, the appropriate concentration is 5 to 80% by weight.

Suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. Examples of surfactants and dispersants include dinaphthylmethanesulfonate, alcohol sulfate, alkylarylsulfonate, ligninsulfonate, polyoxyethylene glycol ether, polyoxyethylene alkylaryl ether, and polyoxyethylene sorbitan monoalkylate. Examples of adjuvants include carboxymethylcellulose.

The agricultural and horticultural fungicide of the present invention can be used as is or diluted by foliage spray, seed treatment, soil application, water surface application, or nursery box application, etc. The application amount varies depending on the type of compound used, target disease, occurrence tendency, degree of damage, environmental conditions, formulation used, etc. For example, when used as is as a dust or granule, the active ingredient is applied in an amount of 0.1 g to 5 kJ/10 ares.
When used in liquid form such as an emulsifiable concentrate or wettable powder, the concentration is preferably selected from the range of 0.1 ppm to 10,000 ppm, preferably 10 to 3,000 ppm.

The compounds according to the invention, when applied in the above-mentioned forms, are effective against the fungi Oomycetes.
, Ascomycetes, Basidiomycetes
es) and Fungi Imperfecti (Deuteromycetes). Specific fungal names are listed below as non-limiting examples: Pseudoperonospora genus, for example, Pseudoperonospora cubensis, Venturia genus, for example, Venturia apple scab, and the like.
inaequalis), Erysiphe fungi, such as wheat powdery mildew (Erysiphe graminis), Pyricularia
Pyricularia, for example, rice blast fungus (Pyricularia
oryzae), Botrytis genus, for example, Botrytis cinerea, Rhizoctonia
Rhizoctonia genus fungi, for example, rice sheath blight fungus (Rhizoctonia solan)
i), Puccinia genus, for example wheat leaf rust fungus (Puc
cinia recondita), Septoria fungi, for example, Septoria nodorum, Sclerotinia fungi, for example, Sclerotinia sclerotinia,
nia sclerotiorum).

Furthermore, the compound of the present invention may be mixed with insecticides, other fungicides, herbicides, plant growth regulators, fertilizers, etc. as needed. Next, typical formulation examples of the agricultural and horticultural fungicide of the present invention will be given and the formulation method will be specifically explained. In the following explanation, "%" indicates percentage by weight.

Formulation Example 1: Dust 2% of compound (A-30), 5% of diatomaceous earth and 93% of clay were uniformly mixed and ground to prepare a dust.

Formulation Example 2 Wettable Powder 50% of compound (A-31), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to give a wettable powder.

Formulation Example 3 Emulsion Compound (A-109) 30%, cyclohexanone 20%, polyoxyethylene alkylaryl ether 11%, calcium alkylbenzenesulfonate 4%
and 35% of methylnaphthalene were uniformly dissolved to prepare an emulsion.

Formulation Example 4 Granules Compound (A-45) 5%, sodium salt of lauryl alcohol sulfate 2%
%, 5% sodium lignosulfonate, 2% carboxymethylcellulose, and 86% clay were uniformly mixed and ground. 20% water was added to this mixture, which was then kneaded and processed into 14-32 mesh granules using an extrusion granulator, and then dried to form granules.

Next, the effects of the agricultural and horticultural fungicide of the present invention will be specifically explained by way of test examples.

Test Example 1: Test of preventive effect against wheat powdery mildew Ten wheat seeds (variety: Norin 61) were sown in each 6 cm diameter plastic pot and grown in a greenhouse. A wettable powder prepared according to Formulation Example 2 was diluted with water to an active ingredient concentration of 500 ppm and sprayed at a rate of 10 ml per pot onto wheat seedlings with two leaves developed. After air drying, the powdery mildew fungus (Erysi
The plants were inoculated with spores of P. phe graminis and kept in a greenhouse. Ten days after inoculation, the diseased area of the first leaves in the entire pot was examined and evaluated according to the criteria in Table 21. The results are shown in Table 22.

Test Example 2: Test of wheat blight prevention effect Ten wheat seeds (variety: Norin 61) were sown in each 6 cm diameter plastic pot and grown in a greenhouse. A wettable powder prepared according to Formulation Example 2 was diluted with water to an active ingredient concentration of 50 ppm on wheat seedlings with two leaves developed.
10 ml of the solution was sprayed per pot. After air drying, the solution was sprayed with wheat leaf spot fungus (Septoria
The plants were inoculated with pycnospores of P. nodorum and kept in a greenhouse. Ten days after inoculation, the diseased area of the first leaves in the entire pot was examined and evaluated according to the criteria in Table 21. The results are shown in Table 23.
shown in.

Test Example 3: Test of preventive effect against gray mold in cucumber Four cucumber seeds (variety: Sagami Hanjiro) were sown in each 6 cm diameter plastic pot and grown in a greenhouse.
The wettable powder prepared in accordance with the above procedure was diluted with water to 500 ppm of active ingredient, and
10 ml of the solution was sprayed per pot. After air drying, the solution was treated with cucumber Botrytis cinerea (Botrytis cinerea).
Paper disks soaked in a spore suspension of B. tis cinerea were placed on the surface of cucumber cotyledons for inoculation, and the pot was immediately placed in a humid chamber at 22°C. Three days after inoculation, the diseased area of the cotyledons in the entire pot was examined and evaluated according to the criteria in Table 24. The results are shown in Table 25.

INDUSTRIAL APPLICABILITY The agricultural and horticultural fungicide of the present invention has a high control effect against cucumber downy mildew, apple scab, wheat powdery mildew, rice blast, cucumber gray mold, rice sheath blight, wheat leaf rust, wheat spot blight, cucumber sclerotinia rot, etc., and is also characterized by not causing phytotoxicity to crops and by having excellent residual efficacy and rain resistance.
It is useful as an agricultural and horticultural fungicide.

───────────────────────────────────────────────────────── Continued from the front page (51) Int.Cl. ⁷ Identification Symbol FI A01N 47/28 102 A01N 47/28 102 C07C 271/22 C07C 271/22 275/24 275/24 317/18 317/18 323/12 323/12 327/58 327/58 327/60 327/60 333/04 333/04 C07D 213/30 C07D 213/30 213/64 213/64 213/65 213/65 213/70 213/70 213/74 213/74 213/79 213/79 213/81 213/81 213/84 213/84 Z 215/14 215/14 215/22 215/22 237/14 237/14 239/26 239/26 239/34 239/34 239/56 239/56 239/60 239/60 277/24 277/24 277/64 277/64 295/08 295/08 Z 303/20 303/20 307/12 307/12 317/22 317/22 (81) Designated countries EP (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), OA (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG), AP (GH, GM, K E, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW), UA (AM, AZ, BY, KG, KZ, MD, RU, TJ, TM), AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, CA, C H, CN, CR, CU, CZ, DE, DK, DM, DZ, EE, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR, TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW (72) Inventor: Norihisa Yonekura, 408 Shionden, Fukuda-cho, Iwata-gun, Shizuoka Prefecture, Japan. 647-1 Tsukiji, Fujieda City, Shizuoka Prefecture, Japan B-102 (72) Inventor Kawashima Takahiro 1-18-6 Nishihara, Kashiwa City, Chiba Prefecture (72) Inventor Sakai Junetsu 992-40 Wada, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Muramatsu Norimichi 15-11 Kuzugaoka 3-chome, Kakegawa-shi, Shizuoka Prefecture (72) Inventor Takagaki Makiichi 2-4-9 Aobadai, Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture (72) Inventor Nagayama Kozo 2384-4 Yasaka, Kakegawa-shi, Shizuoka Prefecture (Note) This publication is based on the gazette published internationally by the International Bureau of Patents (WIPO). The effect of the international publication of the Japanese patent application (Japanese utility model registration application) related to this publication arises pursuant to Article 184-10, Paragraph 1 of the Patent Act (Article 48-13, Paragraph 2 of the Utility Model Act), and is unrelated to this publication.

Claims (8)

[Claims] [Claim 1] General formula [I]{wherein X is a halogen atom, C₁~C₆Alkyl group, C₁~C₆alkoxy groups,
C₁~C₆haloalkyl group or C₁~C₆represents a haloalkoxy group, n is 0 or
represents an integer from 1 to 4; R¹is C₁~C₆represents an alkyl group, and R²is a hydrogen atom,
C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, C
₁~C₆Alkoxy group, C₁~C₆Alkoxy C₁~C₆Alkyl group, C₁~C
₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group, C₁~C₆Al
Kilcarbonyl C₁~C₆represents an alkyl group or an optionally substituted benzyl group,
R³is a hydrogen atom or C₁~C₆represents an alkyl group, and G is an oxygen atom, a sulfur atom, or
-NR⁴- group [R⁴is a hydrogen atom or C₁~C₆represents an alkyl group.
, Y is a hydrogen atom, C₁~C₁₀alkyl groups (which may be the same or different, one or more
, a halogen atom, a cyano group, a nitro group, a hydroxy group, C₃~C₆Cycloalkane
group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆alkylamino groups,
G-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Al
alkylsulfinyl group, carboxyl group, C₁~C₆Alkylcarbonyl group, C₁
~C₆Alkoxycarbonyl group, C₁~C₆Alkoxyimino group or C(O)N
R⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Al
C may be substituted with an alkyl group₂~C₁₀alkenyl groups (the groups are the same
or different one or more of a halogen atom, a cyano group, a nitro group, a hydroxy group,
C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C
₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello Aruki
group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or
is C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C
₁~C₆(representing an alkyl group), C₂~C₁₀Alkynyl group
(The group may be the same or different and may contain one or more of a halogen atom, a cyano group, a nitro group, a cyclohexyl ...
chloroalkyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁
~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Archi
Ruthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁
~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶teeth
The same or different hydrogen atoms or C₁~C₆may be substituted with an alkyl group
I), C₃~C₆Cycloalkyl groups (which may be the same or different, and may contain one or more halo groups)
aryl atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl
Group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino
Base, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁
~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkyl Carbo
Nyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where,
R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆(representing an alkyl group)
may be replaced), C₃~C₆Cycloalkenyl groups (the groups may be the same or different)
At least one halogen atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~
C₆Alkenyl group, hydroxy group, C₂~C₆Alkynyl group, amino group, mono C
₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Al
Koxy group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆
Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵
R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Alkyl
a phenacyl group (which may be substituted with one or more identical or different groups);
The above halogen atoms, C₁~C₆Alkyl group, C₁~C₆Alkoxy group, C₁
~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group or C₁~C₆Arco
aryl groups (which may be the same or different)
One or more halogen atoms, cyano groups, nitro groups, C₁~C₆Alkyl group, C₂
~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Al
Oxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Archi
C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C
₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR
⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Archi
a heteroaryl group (which may be substituted with the same or different alkyl groups);
one or more halogen atoms, cyano groups, nitro groups, C₁~C₆Alkyl group, C
₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆a
Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Al
alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~
C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)N
R⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Al
aryl-C₁~C₆Alkyl group (the group
The aryl may be the same or different and may be one or more of a halogen atom, a cyano group, a nitro group,
, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆alkynyl groups,
an optionally substituted phenoxy group, a hydroxy group, C₁~C₆Alkoxy group, amino
Noki, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C
₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Haloalkoki
C group, C₁~C₆Alkylcarbonyl group, C₁~C₆an alkoxycarbonyl group,
C₁~C₆Alkoxyimino C₁~C₆Alkyl group or C(O)NR⁵R⁶(child
So, R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Indicates an alkyl group
), aryl-C₂~C₆Alkenyl groups (aryl groups of the
are the same or different, and each represents one or more of a halogen atom, a cyano group, a nitro group, C₁~C
₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy
Group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di
-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello
alkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl
group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or
is C₁~C₆alkyl group) or heterocycle-C₁~C
₆alkyl groups, the heterocycles of which may be the same or different, containing one or more halogen atoms,
Cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~
C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C
₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Al
Chilthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C
₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶
are the same or different hydrogen atoms or C₁~C₆It may be substituted with an alkyl group
Q represents a hydrogen atom, a haloalkyl group, a cyano group, or C₁~C₆Alkyl
Group, C₃~C₆Cycloalkyl group, C₁~C₄Alkylthio group, C₁~C₄Al
alkylsulfinyl group, C₁~C₄Alkyl sulfonyl group or phenyl group (the group
is one or more halogen atoms, cyano groups, nitro groups, C₁~C₄Alkyl group, C
₂~C₄Alkenyl group, C₂~C₄Alkynyl group, hydroxy group, C₁~C₄a
Alkoxy group, C₁~C₄Haloalkyl group, C₁~C₄Haloalkoxy group, C₁~
C₄Alkylcarbonyl group or C₁~C₄The alkoxycarbonyl group is substituted
(which may also be used)}. Claim 2: Y is a hydrogen atom, C₁~C₁₀substituted alkyl groups (the groups may be identical or
one or more different halogen atoms, cyano groups, nitro groups, hydroxy groups, C₃~
C₆Cycloalkyl group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆a
alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group
, C₁~C₆Alkyl sulfinyl group, carboxyl group, C₁~C₆Alkylka
Carbonyl group, C₁~C₆Alkoxycarbonyl group, C₁~C₆Alkoxyimino
group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or
is C₁~C₆(representing an alkyl group), C₂~C₁₀Alkenyl
groups (the groups may be the same or different and may be one or more of a halogen atom, a cyano group, a nitro group,
Hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkyria
Amino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~
C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxy
Carbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different
Hydrogen atom or C₁~C₆(representing an alkyl group), C₂~C_1
0Alkynyl groups (which may be the same or different and may contain one or more halogen atoms, cyano groups,
, a nitro group, a cycloalkyl group, a hydroxy group, C₁~C₆Alkoxy group, amino
Noki, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C
₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcal
Bonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where
, R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆(representing an alkyl group)
optionally substituted), C₃~C₆Cycloalkyl groups (the groups may be the same or different)
At least one halogen atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~
C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Arco
Oxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Alkyl
Amino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆
Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵
R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Alkyl
group), C₃~C₆Cycloalkenyl groups (the groups are the same
or different one or more of a halogen atom, a cyano group, a nitro group, C₁~C₆Al
Kill group, C₂~C₆Alkenyl group, hydroxy group, C₂~C₆Alkynyl group,
Amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆alkylamino groups,
C₁~C₆Alkoxy group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl
Group, C₁~C₆Alkylcarbonyl group, C₁~C₆an alkoxycarbonyl group or
C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁
~C₆alkyl group), phenacyl group (the groups may be the same or
or different one or more halogen atoms, C₁~C₆Alkyl group, C₁~C₆Al
Koxy group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group or C
₁~C₆an aryl group (which may be substituted with an alkoxycarbonyl group); an aryl group (which may be substituted with an alkoxycarbonyl group);
one or more different halogen atoms, cyano groups, nitro groups, C₁~C₆a
alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl groups, hydroxy groups,
C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C
₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello Aruki
group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or
is C(O)NR⁵R⁶(where R⁵R⁶are the same or different hydrogen atoms or C₁
~C₆a heteroaryl group (which may be substituted with an alkyl group);
one or more different halogen atoms, cyano groups, nitro groups, C₁~C₆a
alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl groups, hydroxy groups,
C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C
₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Hello Aruki
group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or
is C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C
₁~C₆alkyl group), aryl-C₁~C₆Al
alkyl groups (the aryl groups may be the same or different and may contain one or more halogen atoms, cyano
group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆a
an alkynyl group, an optionally substituted phenoxy group, a hydroxy group, C₁~C₆Arco
Oxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Alkyl
Amino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆
Haloalkoxy group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxyka
Carbonyl group, C₁~C₆Alkoxyimino C₁~C₆Alkyl group or C(O)N
R⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Al
aryl-C₂~C₆Alkenyl group (the
The aryl group may be the same or different and may contain one or more halogen atoms, cyano groups, nitro groups,
Group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group
, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkyl
Amino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁
~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alcoki
carbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different
a hydrogen atom or C₁~C₆alkyl group) or hetero
Ring-C₁~C₆alkyl groups (the heterocycles of which may be the same or different, and may be one or more heterocycles)
halogen atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Arkeny
group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino
Noki, Mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C
₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcal
Bonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where
, R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆(representing an alkyl group)
2. The carbamate derivative according to claim 1, which is represented by the formula: 3. Y is a hydrogen atom, C₂~C₁₀Alkenyl groups (the groups may be the same or different)
one or more of a halogen atom, a cyano group, a nitro group, a hydroxy group, C₁~C
₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆
Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C
₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O
) NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆
(representing an alkyl group), C₂~C₁₀Alkynyl groups (the groups are
The same or different one or more halogen atoms, cyano groups, nitro groups, cycloalkenyl groups,
alkyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆a
alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group
, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆a
Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or
are different hydrogen atoms or C₁~C₆(representing an alkyl group), C
₃~C₆Cycloalkyl groups (which may be the same or different and may contain one or more halogen atoms)
, cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂
~C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono
C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆a
alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆alkylcarbonyl groups,
C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R
⁶are the same or different hydrogen atoms or C₁~C₆(representing an alkyl group)
(C)₃~C₆Cycloalkenyl groups (which may be the same or different, or may be one or more
, a halogen atom, a cyano group, a nitro group, C₁~C₆Alkyl group, C₂~C₆Al
phenyl group, hydroxy group, C₂~C₆Alkynyl group, amino group, mono C₁~C₆
Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆alkoxy group
, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Alkyl
Carbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(child
So, R⁵, R⁶is one or different hydrogen atoms or C₁~C₆Indicates an alkyl group
), a phenacyl group (which may be substituted with one or more of the same or different
Halogen atoms, C₁~C₆Alkyl group, C₁~C₆Alkoxy group, C₁~C₆Ha
alkyl group, C₁~C₆Alkylcarbonyl group or C₁~C₆Alkoxycal
and aryl groups (which may be the same or different, and may be substituted with one or more aryl groups).
a halogen atom, a cyano group, a nitro group, C₁~C₆Alkyl group, C₂~C₆a
Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆alkoxy group
, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino
Group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Archi
carbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶(
Here, R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Indicates an alkyl group
a heteroaryl group (which may be substituted with one or more of the same or different aryl groups);
Above, halogen atoms, cyano groups, nitro groups, C₁~C₆Alkyl group, C₂~C₆
Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁~C₆Alkoxy
Group, amino group, mono C₁~C₆Alkylamino group, di-C₁~C₆Alkylamine
group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Al
alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C(O)NR⁵R⁶
(where R⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Alkyl groups
(Optionally substituted with) aryl-C₁~C₆Alkyl group (the aryl group of the
The group may be the same or different and may be one or more of a halogen atom, a cyano group, a nitro group, a C₁~
C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl groups, substituted
A phenoxy group, a hydroxy group, C₁~C₆Alkoxy group, amino group, mono
No.C₁~C₆Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆
Alkylthio group, C₁~C₆Haloalkyl group, C₁~C₆Haloalkoxy group, C
₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group, C₁~C
₆Alkoxyimino C₁~C₆Alkyl group or C(O)NR⁵R⁶(where R
⁵, R⁶are the same or different hydrogen atoms or C₁~C₆Substituted with an alkyl group
may be selected from the group consisting of aryl-C₂~C₆Alkenyl groups (the aryls of the groups are the same or
or different one or more halogen atoms, cyano groups, nitro groups, C₁~C₆Archi
group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C_{1
~C 6}Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~
C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl groups
, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C
(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~
C₆alkyl group) or heterocycle-C₁~C₆Archi
a heterocyclic group (the heterocyclic rings of which may be the same or different and may contain one or more halogen atoms, cyano groups,
, nitro group, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Al
Quinyl group, hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆
Alkylamino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio
Group, C₁~C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆
Alkoxycarbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶Are they the same?
or different hydrogen atoms or C₁~C₆(which may be substituted with alkyl groups)
2. The carbamate derivative of claim 1, wherein: 4. The compound according to claim 1, wherein Y is an aryl-C ₁ -C ₆ alkyl group, the aryl of which may be the same or different and which is selected from the group consisting of one or more of a halogen atom, a cyano group, a nitro group, a C ₁ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₂ -C 6 alkynyl group, an optionally substituted phenoxy group, a hydroxy group, a C 1 -C 6 alkoxy group, an amino group, a mono-C 1 -C ₆ alkyl group, a hydroxy group, a C 1 -C 6 alkoxy group, an amino group, a mono-C ₁ -C ₆ alkyl group, a hydroxy group, a mono-C 1 -C 6 alkoxy group, a mono-C 1 -C 6 alkyl group, a mono-C ₁ -C 6 alkoxy ...
₆ alkylamino group, di- _C1 - _C6 alkylamino group, _C1 - _C6 alkylthio group, _C1 - _C6 haloalkyl group, _C1 - _C6 haloalkoxy group, _C1 - _C6 alkylcarbonyl group, _C1 - _C6 alkoxycarbonyl group, _C1 - _C6 alkoxyiminoC1 _{-C6 alkyl} group or C(O) ^NR5R6 (wherein ^{R5 and R6 are} the same or different and may be substituted with a hydrogen atom or a _C1 - _C6 alkyl group). 5. Y is heterocycle-C₁~C₆Alkyl groups (the heterocycles of the groups are the same or
or different one or more halogen atoms, cyano groups, nitro groups, C₁~C₆Archi
group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydroxy group, C₁
~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~
C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl groups
, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl group or C
(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C₁~
C₆The compound according to claim 1, which is represented by the formula (which may be substituted with an alkyl group).
-bamate derivatives. 6. Y is heteroaryl-C₁~C₆Alkyl group (heteroaryl group)
The group may be the same or different and may contain one or more halogen atoms, cyano groups, nitro groups, C₁
~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆Alkynyl group, hydro
oxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group
, J-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Ha
alkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxycarbonyl
Nyl group or C(O)NR⁵R⁶(where R⁵, R⁶may be the same or different hydrogen atoms
Child or C₁~C₆The scope of the claims is represented by (which may be substituted with) an alkyl group.
A carbamate derivative according to Box 1. 7. Y is a benzyl group (which may be the same or different and may contain one or more halogen atoms).
Atom, cyano group, nitro group, C₁~C₆Alkyl group, C₂~C₆alkenyl groups,
C₂~C₆an alkynyl group, an optionally substituted phenoxy group, a hydroxy group, C₁
~C₆Alkoxy group, amino group, mono C₁~C₆Alkylamino group, di-C₁~
C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~C₆Haloalkyl groups
, C₁~C₆Haloalkoxy group, C₁~C₆Alkylcarbonyl group, C₁~C₆
Alkoxycarbonyl group, C₁~C₆Alkoxyimino C₁~C₆Alkyl group or
is C(O)NR⁵R⁶(where R⁵, R⁶are the same or different hydrogen atoms or C
₁~C₆alkyl group) or containing one or more nitrogen atoms
Heteroaryl-C represented by a 5- or 6-membered ring₁~C₆Alkyl group (hetero group of said group)
The aryl may be the same or different and may contain one or more halogen atoms, cyano groups, nitro groups, or the like.
, C₁~C₆Alkyl group, C₂~C₆Alkenyl group, C₂~C₆alkynyl groups,
Hydroxy group, C₁~C₆Alkoxy group, amino group, mono C₁~C₆Alkyria
Amino group, di-C₁~C₆Alkylamino group, C₁~C₆Alkylthio group, C₁~
C₆Haloalkyl group, C₁~C₆Alkylcarbonyl group, C₁~C₆Alkoxy
Carbonyl group or C(O)NR⁵R⁶(where R⁵, R⁶are the same or different
Hydrogen atom or C₁~C₆It may be substituted with an alkyl group.
The carbamate derivative according to claim 1. 8. An agricultural and horticultural fungicide containing the carbamate derivative according to any one of claims 1 to 7 as an active ingredient.