JPH0656756A - N-phenylcarbamate compound, its production and noxious life controlling agent containing the compound - Google Patents

Abstract

PURPOSE:To provide the new compound useful as a noxious life controlling agent for agricultural and horticultural use. CONSTITUTION:The compound of formula I [R<1> is a (substituted) alkyl; R<2> is a (substituted) alkyl, (substituted) alkenyl, (substituted) cycloalkyl, etc.; R<3> is a (substituted) alkyl, (substituted) cycloalkyl, (substituted) alkenyl, etc.; R<4> is H, (substituted) alkyl, (substituted) cycloalkyl, (substituted) phenyl, etc.; A is H, halogen, (substituted) alkyl, etc.; excluding the case that R<3> is a (substituted) alkyl or a (substituted) cycloalkyl and R<4> is a (substituted) phenyl], e.g. methyl-N-[2-[(1,3-dimethyl-2-butenylidene)aminoxymethyl]phenyl]-carbam ate. The compound of formula I can be produced by reacting a compound of formula II with a compound of the formula ClCO2R<1>.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a pesticide for agricultural and horticultural use.

[0002]

2. Description of the Related Art N-phenyl carbamate compounds are
For example, in Table 1 (a) Compound No. 596-598. However, the compound of the present invention represented by the general formula (I) is not disclosed therein.

[0003]

The present invention has the general formula (I)

[0004]

[Chemical 11]

(In the formula, R ¹ is an optionally substituted alkyl group, R ² is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, A cycloalkyl group which may be substituted or a -COX ¹ group, X ¹ is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, or a cycloalkyl which may be substituted. Is a group or an optionally substituted alkoxy group, R ³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or a substituted an alkynyl group which may be, R ⁴ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy , Alkylthio group which may be substituted,
Optionally substituted phenyl group, cyano group, -NR ⁵ R ⁶
Group or a —CO ₂ R ⁷ group, R ³ and R ⁴ may be bonded to each other to form a 4- to 7-membered ring with an adjacent carbon atom, and R ⁵ and R ⁶ are each a hydrogen atom or a substituent. Is an optionally substituted alkyl group, R ⁷ is an optionally substituted alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or an optionally substituted alkoxy group, provided that R ³ is an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and R ⁴
Is a phenyl group which may be substituted), a method for producing them and a pest control agent containing them as an active ingredient.

In the general formula (I), R ¹ , R ² , X ¹ ,
R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ or an optionally substituted alkyl group contained in A, an optionally substituted alkenyl group, an optionally substituted alkynyl group or an optionally substituted cycloalkyl. Examples of the substituent of the group, the cycloalkenyl group which may be substituted, the alkoxy group which may be substituted and the alkylthio group which may be substituted include a halogen atom; a cyano group; an alkoxy which may be substituted with a halogen atom or an alkoxy group. Group; alkylthio group; alkoxycarbonyl group; alkylcarbonyl group; cycloalkyl group; cycloalkenyl group which may be substituted with an alkyl group; nitro group; phenyl group which may be substituted with an alkyl group, an alkoxy group or a methylenedioxy group Or a phenoxy group; and when the number of substitutions is 2 or more, they may be the same or different. It may be.

In the general formula (I), the substituent of the optionally substituted phenyl group contained in R ⁴ is, for example, an alkyl group; an alkoxy group; a methylenedioxy group; a dialkyl-substituted methylenedioxy group; An alkenyloxy group which may be substituted; or an alkynyloxy group which may be substituted with a halogen atom, and the like, and the number of substitutions is 2
In the above cases, they may be the same or different.

Examples of the alkyl group or alkyl moiety contained in the general formula (I) include those having 1 to 6 carbon atoms, such as methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group. The group or alkenyl moiety has 2 to 6 carbon atoms, for example, vinyl group, allyl group, propenyl group, butenyl group, pentenyl group, hexenyl group, pentadienyl group, cyclopentylidenemethyl group, alkynyl group or alkynyl group. Examples of the moiety include those having 2 to 6 carbon atoms, such as an ethynyl group, a propargyl group, a propynyl group, a butynyl group, a pentynyl group, and a hexynyl group, and each of the above groups or moieties is a linear or branched fatty chain. Includes structural isomers of. or,
The cycloalkyl group or the cycloalkyl moiety has 3 to 6 carbon atoms, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and the cycloalkenyl group has 3 to 6 carbon atoms,
Examples thereof include a cyclopentenyl group and a cyclohexenyl group.

Examples of the halogen atom contained in the general formula (I) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. R ³ and R ⁴ may be bonded to each other to form a 4- to 7-membered ring with the adjacent carbon atom.
The ~ 7-membered ring may contain oxygen or sulfur atoms and may contain one or two fused aromatic rings. Examples of these 4- to 7-membered rings include dihydrobenzopyran, dihydrobenzothiopyran, indane, tetrahydronaphthalene, and cyclopentene.
Further, it may have one or more substituents such as alkyl and alkoxy.

The compound represented by the general formula (I) has geometrical isomers of E and Z isomers with respect to R ³ and R ⁴ , and each isomer and a mixture of isomers are essentially the same. Included in the invention.

Among the compounds represented by the general formula (I), the following are preferable. R ¹ is an alkyl group, R ² is an alkyl group which may be substituted with an alkoxy group, R ²
A compound in which ⁴ is an alkyl group and A is a hydrogen atom.

The compound represented by the general formula (I) can be produced, for example, by the following reaction steps 1 to 4.

<Reaction Step 1>

[Chemical 12]

<Reaction Step 2>

[Chemical 13]

<Reaction Step 3>

[Chemical 14]

(During each of the above reaction steps, R ¹ , R ² , R ³ ,
R ⁴ and A are as described above, Y is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or a —COX ¹ group. X ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or an optionally substituted alkoxy group, and W Is a chlorine atom, a bromine atom or an iodine atom)

In reaction step 3, Y is a --COX ² group (X ² is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group or an optionally substituted cycloalkyl group. Is Y), then Y
^(X 2 _CO) 2 O in place of -W ^{(X 2} are as defined above,) can also be used.

<Reaction Step 4>

[Chemical 15]

(Wherein R ¹ , R ³ , R ⁴ , A and W are as described above)

Of the compounds represented by the general formula (II) in the reaction step 1, those in which R ² is a hydrogen atom can be produced, for example, by the method of the following reaction step 5.

<Reaction Step 5>

[Chemical 16]

(Wherein W, R ³ , R ⁴ and A are as described above)

Further, among the compounds represented by the general formula (II) in the reaction step 1, those in which R ² is Y (Y is as described above) are produced, for example, by the method of the following reaction step 6. can do.

<Reaction Step 6>

[Chemical 17]

(Wherein R ³ , R ⁴ , A, W and Y are as described above)

The compound represented by the general formula (III) in the reaction step 2 can be produced, for example, by the method of the following reaction step 7.

<Reaction Step 7> (II-2) + Phosgene → (III)

Among the compounds represented by the general formula (IV) in the reaction step 4, those in which (i) W is a chlorine atom or a bromine atom are a 2-aminobenzyl alcohol derivative and ClCO ₂
R ¹ (R ¹ is as described above) is reacted in the same manner as in the above reaction step 1 to give a compound of the general formula

[0029]

[Chemical 18]

A compound of formula (R ¹ and A is as described above), which can be obtained by conventional chlorination with SOCl ₂ or by conventional bromination with SOBr ₂ or the like, (ii) When W is an iodine atom, it is obtained by reacting the W obtained in (i) above which is a chlorine atom or a bromine atom with an alkali metal iodide such as sodium iodide.

The compounds included in the general formula (II) have the same isomers as those described for the general formula (I).

The reaction steps 1, 3, 4, 5 (1) and 6 are:
It is usually performed in the presence of a solvent and a base. As the solvent, aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated aliphatic hydrocarbons such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane and trichloroethane; cyclic or non-cyclic hydrocarbons such as n-hexane and cyclohexane Cycloaliphatic hydrocarbons; ethers such as diethyl ether, dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; nitriles such as acetonitrile and propionitrile; dimethylformamide, N-
Aprotic polar solvents such as methyl-2-pyrrolidone, dimethyl sulfoxide, sulfolane and the like can be mentioned.
The base may be an inorganic base or an organic base,
Examples of the inorganic base include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metal or alkaline earth metal carbonates such as anhydrous potassium carbonate and anhydrous calcium carbonate; alkali such as sodium hydride. Metal hydride; alkali metals such as sodium metal, and the like, and organic bases include pyridine, triethylamine, and the like. Reaction temperature is usually -1
The reaction time is usually 0.5 to 24 hours at 0 ° C to + 150 ° C.

In the reaction steps 3, 4 and 6,
If necessary, a catalyst such as tetrabutylammonium bromide or a quaternary ammonium salt such as tetra-n-butylammonium hydrogen sulfate can be used.

Reaction step 2 is carried out in the presence of a solvent and / or a catalyst, if necessary. As the solvent, those similar to those used in the reaction steps 1, 3, 4, 5 (1) and 6 can be mentioned, and as the catalyst, triethylamine, diethylaniline, 1,4-diazabicyclo (2,2,2).
Examples include octane. Reaction temperature is usually 0 to 50
C, reaction time is from instant to 10 hours.

The hydrazinolysis of reaction step 5 (2) is
Usually, hydrazine hydrate or the like is used and, if necessary, it is performed in the presence of a solvent such as ethanol.

Reaction step 7 is carried out in the presence of a solvent.
Examples of the solvent include benzene, toluene, xylene, organic solvents such as ethyl acetate, and the like. Reaction temperature is 50
The temperature is from ℃ to reflux temperature, and the reaction time is from instant to 10 hours.

The compound of the present invention represented by the general formula (I) is useful as an active ingredient of a pest controlling agent. For example, as agricultural and horticultural fungicides, rice blast, rice blight, rice sesame leaf blight, cucumber anthracnose, cucumber powdery mildew, cucumber bean disease, tomato blight, tomato ring spot, citrus black spot disease, Green mold of citrus fruits, scab of apples and pears, leaf spot of apple, spot of mildew of pustweed, various types of gray mold, sclerotium, rust and other diseases and Fusarium bacterium, Pythium bacterium, Rhizoctonia bacterium, Verticillium It shows an excellent control effect against soil diseases caused by plant pathogens such as fungi and Plasmodiophora. Especially excellent against rice blast, cucumber anthracnose, various powdery mildew, various gray mold, sclerotial disease, various rust, downy mildew of cucumber and puto, plague of tomato and potato, etc. It shows a controlling effect. Since the compound of the present invention has a long residual effect and an excellent preventive effect as well as an excellent therapeutic effect, it is possible to control diseases by treatment after infection. Further, disease control by soil treatment is also possible. INDUSTRIAL APPLICABILITY The compounds of the present invention are not only susceptible bacteria but also various resistant bacteria (benomoyl-resistant powdery mildew, metalaxyl-resistant downy mildew, benomyl and / or
Alternatively, it is also effective against dicarboximide compound resistant Botrytis cinerea etc.).

The compound of the present invention also has an insecticidal activity, an acaricidal activity and a nematicidal activity, and is effective against various harmful insects.

When the compound of the present invention is used, it may be formulated into various forms such as emulsions, powders, wettable powders, liquids, granules, suspensions and the like, together with auxiliary agents, as in the case of conventional pesticide formulations. You can In the actual use of these preparations, they can be used as they are or diluted with a diluent such as water to a predetermined concentration and used. Examples of the auxiliary agent here include a carrier, an emulsifier, a suspending agent, a dispersing agent, a spreading agent,
Examples include penetrants, wetting agents, thickeners, stabilizers, and the like, which may be appropriately added as necessary.

The carrier is divided into a solid carrier and a liquid carrier. As the solid carrier, starch, sugar, cellulose powder, cyclodextrin, activated carbon, soybean powder, wheat flour, chaff powder, wood flour, fish meal, milk powder and other animal and plant powders; talc, kaolin, bentonite, organic bentonite, calcium carbonate, Calcium sulfate, sodium bicarbonate, zeolite, diatomaceous earth, white carbon, clay, alumina, silica, sulfur powder and other mineral powders can be used. Liquid carriers include water; soybean oil, cottonseed oil, corn oil and other animal and vegetable oils. Alcohols such as ethyl alcohol and ethylene glycol; ketones such as acetone and methyl ethyl ketone; ethers such as dioxane and tetrahydrofuran; aliphatic hydrocarbons such as kerosene, kerosene and liquid paraffin; xylene, trimethylbenzene, tetramethylbenzene, Shiku Aromatic hydrocarbons such as hexane and solvent naphtha; halogenated hydrocarbons such as chloroform and chlorobenzene; acid amides such as dimethylformamide; esters such as ethyl acetate and glycerin ester of fatty acids; nitriles such as acetonitrile; Sulfur-containing compounds such as dimethylsulfoxide; N-methylpyrrolidone and the like.

A suitable compounding weight ratio of the compound of the present invention to the adjuvant is generally 0.05: 99.95 to 90:10, preferably 0.2: 99.8 to 80:20.

The use concentration / use amount of the compound of the present invention varies depending on the target crop, use method, formulation form, application amount and the like and cannot be specified unconditionally, but in the case of foliar treatment, it is usually 0.1 to 0.1 per active ingredient. It is 10,000 ppm, preferably 1 to 2,000 ppm. In the case of soil treatment,
Usually 10 to 100,000 g / ha, preferably 200
~ 20,000 g / ha.

Formulation examples of pest control agents containing the compound of the present invention as an active ingredient are shown below. Formulation Example 1 (1) Compound No. 17: 50 parts by weight (2) Kaolin: 40 parts by weight (3) Sodium lignin sulfonate: 7 parts by weight (4) Polyoxyethylene alkylphenyl ether sulphate: 3 parts by weight A wettable powder is obtained.

Formulation Example 2 (1) Compound No. 19: 20 parts by weight (2) White carbon: 10 parts by weight (3) Kaolin: 62 parts by weight (4) Sodium lignin sulfonate: 4 parts by weight (5) Polyoxyethylene alkylaryl ether ...
... 4 parts by weight The above ingredients are uniformly mixed to obtain a wettable powder.

Formulation Example 3 (1) Compound No. 21: 10 parts by weight (2) Diatomaceous earth: 15 parts by weight (3) Calcium carbonate powder: 69 parts by weight (4) Dialkyl sulfosuccinate: 1 part by weight (5) Polyoxyethylene alkylphenyl ether sulfate: 3 parts by weight (6) β-sodium naphthalenesulfonic acid formalin condensate 2 parts by weight The above ingredients are uniformly mixed to obtain a wettable powder.

Formulation Example 4 (1) Compound No. 23 …… 6 parts by weight (2) Diatomaceous earth …… 88 parts by weight (3) Dialkylsulfosuccinate …… 2 parts by weight (4) Polyoxyethylene alkylphenyl ether sulphate …… 4 parts by weight The above ingredients are mixed uniformly. A wettable powder is obtained.

Formulation Example 5 (1) Compound No. 29: 0.5 parts by weight (2) Talc: 99.0 parts by weight (3) Lower alcohol phosphate ester: 0.5 parts by weight The above components are uniformly mixed to obtain a dust.

Formulation Example 6 (1) Compound No. 25: 0.2 parts by weight (2) Calcium carbonate powder: 98.8 parts by weight (3) Lower alcohol phosphate ester: 1 part by weight The above ingredients are uniformly mixed to obtain a powder.

Formulation Example 7 (1) Compound No. 4: 20 parts by weight (2) Xylene: 60 parts by weight (3) Polyoxyethylene alkylaryl ether ...
20 parts by weight The above components are mixed and dissolved to obtain an emulsion.

Formulation Example 8 (1) Compound No. 33 …… 1 part by weight (2) Bentonite …… 33 parts by weight (3) Kaolin …… 61 parts by weight (4) Sodium lignin sulfonate …… 5 parts by weight Add an appropriate amount of water required for granulation to the above components, Granules are obtained by mixing and granulating.

Formulation Example 9 (1) Compound No. 55 ...... 10 parts by weight (2) Saturated isoparaffin hydrocarbons (fractions 210-2
65 ° C.) 79 parts by weight (3) Mixture of polyoxyethylene phenylphenol derivative and polyoxyethylene sorbitan alkylate ...
10 parts by weight (4) Organic bentonite: 1 part by weight The above components are mixed and finely pulverized to obtain a suspension agent.

Formulation Example 10 (1) Compound No. 2 …… 40 parts by weight (2) Oxyethylated polyarylphenol phosphate-triethanolamine …… 2 parts by weight (3) Silicone …… 0.2 parts by weight (4) Zansan gum …… 0.1 parts by weight ( 5) Ethylene glycol: 5 parts by weight (6) Water: 52.7 parts by weight The above components are uniformly mixed and ground to give an aqueous suspension.

Formulation Example 11 (1) Compound No. 14: 75 parts by weight (2) Sodium polycarboxylate: 13.5 parts by weight (3) Anhydrous sodium sulfate: 10 parts by weight (4) Dextrin: 0.5 parts by weight (5) Sodium alkylsulfonate: 1 part by weight The above components are put in a high speed mixing granulator and further 20
% Water is added, and the mixture is granulated and dried to obtain a wettable granule.

If necessary, the compound of the present invention is mixed with other agricultural chemicals such as insecticides, acaricides, nematicides, fungicides, antiviral agents, attractants, herbicides, plant growth regulators and the like. , Can be used in combination, and in this case, a more excellent effect may be exhibited.

Examples of the active ingredient compounds of the above insecticides, acaricides or nematicides include O- (4-bromo-2)
-Chlorophenyl) O-ethyl S-propyl phosphorothioate (generic name: profenophos), O- (2,2-
Dichlorovinyl) O, O-dimethyl phosphate ((generic name: dichlorvos), O-ethyl O- [3-
Methyl-4- (methylthio) phenyl] N-isopropyl phosphoramidate (generic name: fenamiphos),
O, O-dimethyl O- (4-nitro-m-tolyl) phosphorothioate (generic name: fenitrothion), O-
Ethyl O- (4-nitrophenyl) phenylphosphonothioate (generic name: EPN), O, O-diethyl O
-(2-isopropyl-6-methylpyrimidin-4-yl) phosphorothioate (generic name: diazinon),
O, O-dimethyl O- (3,5,6-trichloro-2
-Pyridyl) phosphorothioate (generic name: chlorpyrifosmethyl), O, S-dimethyl N-acetylphosphoramidothioate (generic name: acephate), O-
(2,4-dichlorophenyl) O-ethyl S-propyl phosphorodithioate (generic name: prothiophos),
An organic phosphate ester compound such as (RS) -S-sec-butyl O-ethyl 2-oxo-1,3-thiazolidin-3-ylphosphonothioate (a compound described in US Pat. No. 4,590,182);

1-naphthyl N-methylcarbamate (generic name: alvalyl), 2-isopropoxyphenyl N-methylcarbamate (generic name: propoxur),
2-methyl-2- (methylthio) propionaldehyde O-methylcarbamoyl oxime (generic name: aldicarb), 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N-methylcarbamate (generic name: carbofuran), Dimethyl N, N '-[thiobis {(methylimino) carbonyloxy}] bisethaneimidothioate (generic name: thiodicarb), S-methyl N-
(Methylcarbamoyloxy) thioacetimidate (generic name: Mesomel), N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide (generic name: oxamyl), 2- (ethylthiomethyl) phenyl N-methyl carbamate (generic name: etiophencarb), 2-dimethylamino-5,6-dimethylpyrimidin-4-yl N, N-dimethylcarbamate (generic name: pyrimicarb), 2-sec-butylphenyl N-methylcarbamate ( Generic name: carbamate compounds such as Fenobucarb);

S, S'-2-dimethylaminotrimethylene bis (thiocarbamate) (generic name: cartap),
Nereistoxin derivatives such as N, N-dimethyl-1,2,3-trithian-5-ylamine (generic name: thiocyclam); 2,2,2-trichloro-1,1-bis (4-chlorophenyl) ethanol (Generic name: dicofol), 4-chlorophenyl-2,4,5-trichlorophenyl sulfone (generic name: tetradiphone) such as an organic chlorine compound; bis [tris (2-methyl-2-phenylpropyl) tin] oxide An organometallic compound such as (generic name: fenbutatin oxide);

(RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-chlorophenyl) -3-methylbutyrate (generic name: fenvalerate), 3-phenoxybenzyl (1RS) -cis, Transformer-3-
(2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: permethrin),
(RS) -α-cyano-3-phenoxybenzyl (1R
S) -cis, trans-3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: cypermethrin), (S) -α-cyano-
3-phenoxybenzyl (1R) -cis-3- (2,2
-Dibromovinyl) -2,2-dimethylcyclopropanecarboxylate (generic name: deltamethrin), (R
S) -α-Cyano-3-phenoxybenzyl (1RS)
-Cis, trans-3- (2-chloro-3,3,3-trifluoropropenyl) -2,2-dimethylcyclopropanecarboxylate (generic name: cyhalothrin), 4-
Methyl-2,3,5,6-tetrafluorobenzyl-3
-(2-chloro-3,3,3-trifluoro-1-propenyl) -2,2-dimethylcyclopropanecarboxylate (generic name: tefluthrin), 2- (4-ethoxyphenyl) -2-methylpropyl 3 -Pyrethroid compounds such as phenoxybenzyl ether (generic name: Etofenprox);

1- (4-chlorophenyl) -3- (2,
6-difluorobenzoyl) urea (generic name: diflubenzuron), 1- [3,5-dichloro-4- (3-chloro-5-trifluoromethyl-2-pyridyloxy) phenyl] -3- (2,6- Difluorobenzoyl) urea (generic name: chlorfluazuron), 1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6
-Difluorobenzoyl) urea (generic name: teflubenzuron) benzoylurea compound; isopropyl (2E, 4E) -11-methoxy-3,7,11
-Trimethyl-2,4-dotecadienoate (generic name:
Juvenile hormone-like compounds such as methoprene);

Pyridazinone compounds such as 2-t-butyl-5- (4-t-butylbenzylthio) -4-chloro-3 (2H) -pyridazinone (generic name: pyridaben); t-butyl 4- [ (1,3-Dimethyl-5-phenoxypyrazol-4-yl) methyleneaminooxymethyl] benzoate (generic name: fenpyroximate)
A pyrazole compound such as;

1- (6-chloro-3-pyridylmethyl)
-N-nitro-imidazolidine-2-ylideneamino (generic name: imidacloprid), 1- [N- (6-chloro-3-pyridylmethyl) -N-ethylamino] -1-
Methylamino-2-nitroethylene (European publication N
o. 302389), 2-methylamino-2- [N-methyl-N- (6-chloro-3-pyridylmethyl) amino] -1-nitroethylene (European publication No. 30).
2389), 1- (6-chloro-3-pyridylmethyl)
Amino-1-dimethylamino-2-nitroethylene (European publication No. 302389), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-allylthioethylidene) imidazolidine (European publication) N
o. 437784), 1- (6-chloro-3-pyridylmethyl) -2- (1-nitro-2-ethylthioethylidene) imidazolidine (European Publication No. 43778).
4), 1- (6-chloro-3-pyridylmethyl) -2-
(1-Nitro-2-β-tolylallylthioethylidene)
Imidazolidine (European publication No. 43778
4), 1- (6-chloro-3-pyridylmethyl) -3-
Methyl-2-nitroguanidine (European publication No.
383091), 1- (6-chloro-3-pyridylmethyl) -3,3-dimethyl-2-nitroguanidine (European Publication No. 383091), 3- (6-chloro-).
3-pyridylmethyl) -2-nitromethylene-thiazolidine (European publication No. 192060), 1- (6
-Chloro-3-pyridylmethyl) -2- (nitromethylene) -imidazolidine (European publication No. 1638)
55), 6- (6-chloro-3-pyridylmethylamino) -1,3-dimethyl-5-nitro-1,2,3,4
-Tetrahydropyrimidine (European publication No. 36
6085), 1- (6-chloro-3-pyridylmethyl)
-5-nitro-3-methyl-6-methylamino-1,
Nitro compounds such as 2,3,4-tetrahydropyrimidine (European publication No. 366085);

Dinitro compounds, organic sulfur compounds, urea compounds, triazine compounds, hydrazine compounds,
In addition, as other compounds, 2-tert-butylimino-3-isopropyl-5-phenyl-3,4,5,5
6-Tetrahydro-2H-1,3,5-thiadiazine-
4-one (generic name: buprofezin), trans- (4
-Chlorophenyl) -N-cyclohexyl-4-methyl-2-oxothiazolidinone-3-carboxamide (generic name: hexithiazox), N-methylbis (2,4-
Xylyliminomethyl) amine (generic name: amitraz), N ′-(4-chloro-o-tolyl) -N, N-dimethylformamidine (generic name: chlordimeform),
(4-Ethoxyphenyl)-[3- (4-fluoro-3
-Phenoxyphenyl) propyl] (dimethyl) silane (generic name: silafluophene); and the like. Further, they can be mixed and used in combination with microbial agents such as BT agents and insect pathogenic virus agents, antibiotics such as avermectin and milbemycin.

Examples of the active ingredient compound of the bactericide include pyrimidinamine-based compounds such as 2-anilino-4-methyl-6- (1-propynyl) pyrimidine (the compound described in Japanese Patent Laid-Open No. 63-208581). ;

1- (4-chlorophenoxy) -3,3-
Dimethyl-1- (1H-1,2,4-triazole-1
-Yl) butanone (generic name: triadimefon), 1-
(Biphenyl-4-yloxy) -3,3-dimethyl-
1- (1H, 1,2,4-triazol-1-yl) butan-2-ol (generic name: bitertanol), 1-
[N- (4-chloro-2-trifluoromethylphenyl) -2-propoxyacetimidoyl] imidazole (generic name: triflumizole), 1- [2- (2,4-
Dichlorophenyl) -4-ethyl 1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole (generic name: etaconazole), 1- [2- (2,4-dichlorophenyl) -4-propyl- 1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole (generic name: propiconazole), 1- [2- (2,4
-Dichlorophenyl) pentyl] -1H-1,2,4-
Triazole (generic name: penconazole), bis (4-
Fluorophenyl) (methyl) (1H-1,2,4-triazol-1-ylmethyl) silane (generic name: flusilazole), 2- (4-chlorophenyl) -2- (1H
-1,2,4-triazol-1-ylmethyl) hexanenitrile (generic name: microbutanyl), (2RS,
3RS) -2- (4-Chlorophenyl) -3-cyclopropyl-1- (1H-1,2,4-triazole-1-
(Il) butan-2-ol (generic name: cyproconazole), (RS) -1- (4-chlorophenyl) -4,4
-Dimethyl-3- (1H-1,2,4-triazole-
1-ylmethyl) pentan-3-ol (generic name: turbuconazole), (RS) -2- (2,4-dichlorophenyl) -1- (1H-1,2,4-triazole-1)
-Yl) hexan-2-ol (generic name: hexaconazole), (2RS, 5RS) -5- (2,4-dichlorophenyl) tetrahydro-5- (1H-1,2,4-triazol-1-ylmethyl ) -2-Frill 2,2,2
-Trifluoroethyl ether (generic name: farconazole cis), N-propyl-N- [2- (2,4,6-
Azole compounds such as trichlorophenoxy) ethyl] imidazole-1-carboxamide (generic name: prochloraz);

6-methyl-1,3-dithiolo [4,5-
b] A quinoxaline compound such as quinoxalin-2-one (general name: quinomethionate); a polymer of manganese ethylenebis (dithiocarbamate) (general name: manneb), zinc ethylenebis (dithiocarbamate)
Polymer (generic name: zineb), complex compound of zinc (zinc) and manganese ethylene bis (dithiocarbamate) (manneb) (generic name: manzeb), dizinc bis (dimethyldithiocarbamate) ethylene bis (dithiocarbamate) (general) Name: polycarbamate), dithiocarbamate compound such as zinc propylene bis (dithiocarbamate) polymer (general name: propineb);

Organochlorine compounds such as 4,5,6,7-tetrachlorophthalide (generic name: fthalide), tetrachloroisophthalonitrile (generic name: chlorothalonil), pentachloronitrobenzene (generic name: quintozene) Methyl 1- (butylcarbamoyl) benzimidazol-2-ylcarbamate (generic name: benomyl), dimethyl 4,4 ′-(o-phenylene) bis (3
-Thialophanate) (generic name: thiophanate methyl), benzimidazole compounds such as methylbenzimidazol-2-ylcarbamate (generic name: carbendazim); 3-chloro-N- (3-chloro-2,6)
-Dinitro-4-α, α, α-trifluorotolyl)-
5-trifluoromethyl-2-pyridinamine (generic name:
Fluazinam) -like pyridinamine compounds; 1-
A cyanoacetamide compound such as (2-cyano-2-methoxyiminoacetyl) -3-ethylurea (generic name: cimoxanil);

Methyl N- (2-methoxyacetyl)-
N- (2,6-xylyl) -DL-alaninate (generic name: metalaxyl), 2-methoxy-N- (2-oxo-1,3-oxazolidin-3-yl) aceto-2 ',
6'-xylidide (generic name: oxadixyl), (±)
-Α-2-chloro-N- (2,6-xylylacetamide) -γ-butyrolactone (generic name: offlace), methyl N-phenylacetyl-N- (2,6-xylyl) -DL-alaninate ( (Generic name: benalaxyl),
Methyl N- (2-furoyl) -N- (2,6-xylyl) -DL-alaninate (generic name: furaraxyl),
(±) -α- [N- (3-chlorophenyl) cyclopropanecarboxamide] -γ-butyrolactone (generic name:
Phenylamide compounds such as cyprofuran); N-
Dichlorofluoromethylthio-N ', N'-dimethyl-
Sulfenic acid-based compounds such as N-phenylsulfamide (generic name: diclofluanide);

Cupric hydroxide (general name: cupric hydroxide),
Copper-based compounds such as copper 8-quinolinolate (generic name: organic copper); isoxazole-based compounds such as 5-methylisoxazol-3-ol (generic name: hydroxyisoxazole); Aluminum tris (ethylphosphonate) (General name: fosetylaluminum), O-
2,6-dichloro-p-tolyl-O, O-dimethylphosphorothioate (generic name: triclophos-methyl), S
-Organophosphorus compounds such as benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum ethyl hydrogen phosphonate;

N- (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide (generic name: captan), N- (1,1,2,2-tetrachloroethylthio) cyclohex-4-ene-1 , 2-dicarboximide (generic name: captafol), N- (trichloromethylthio) phthalimide (generic name: folpet), N-halogenothioalkyl compounds; N- (3,5
-Dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide (generic name: procymidone), 3- (3,5-dichlorophenyl) -N-isopropyl-2,4-dioxoimidazolidine-1 -Carboxamide (generic name: iprodione), (RS) -3-
Dicarboximide compounds such as (3,5-dichlorophenyl) -5-methyl-5-vinyl-1,3-oxazolidine-2,4-dione (generic name: vinclozolin); α, α, α-trifluoro -3'-isopropoxy-o-toluanilide (generic name: flutolanil), 3 '
A benzanilide compound such as isopropoxy-o-toluanilide (generic name: mepronil);

2- (1,3-dimethylpyrazole-4-
Ilcarbonylamino) -4-methyl-3-pentenenitrile (compound described in British Patent No. 2190375), α- (nicotinylamino)-(3-fluorophenyl) acetonitrile (JP-A 63-135364).
Benzamide-based compounds such as compounds described in
A piperazine-based compound such as N '-[piperazine-1,4-diylbis [(trichloromethyl) methylene]] diformamide (generic name: triphorine); 2', 4'-dichloro-2- (3-pyridyl) acetophenone Pyridine compounds such as O-methyloxime (generic name: pyriphenox); (±) -2,4'-dichloro-α-
(Pyrimidin-5-yl) benzhydryl alcohol (generic name: phenalimol), (±) -2,4'-difluoro-α- (1H-1,2,4-triazol-1-ylmethyl) benzhydryl alcohol A carbinol compound such as (generic name: flutriafol);

A piperidine compound (±) -cis-4- [such as (RS) -1- [3- (4-tert-butylphenyl) -2-methylpropyl] piperidine (generic name: phenpropidin). Morpholine-based compounds such as 3- (4-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine (generic name: phenpropimorph); triphenyltin hydroxide (generic name: phen) Tintin hydroxide), an organotin compound such as triphenyltin acetate (generic name: fentin acetate); 1- (4-chlorobenzyl)
-1-Cyclopentyl-3-phenylurea (generic name:
Urea compounds such as (Pencilculone); (E, Z) 4
A cinnamic acid compound such as-[3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholin (generic name: dimethomorph);

Phenylcarbamate compounds such as isopropyl 3,4-diethoxycarbanilate (generic name: dietofencarb); 3-cyano-4- (2,2)
-Difluoro-1,3-benzodioxol-4-yl) pyrrole (trade name: sapphire), 3- (2 ',
A cyanopyrrole-based compound such as 3'-dichlorophenyl) -4-cyano-pyrrole (generic name: fenpiclonyl);

Atraquinone compounds; crotonic acid compounds; antibiotics and the like. Further, the above general formula (I)
An appropriate mixing weight ratio of the partner agent used in combination with the N-phenylcarbamate compound represented by is generally 1:
300-300: 1, preferably 1: 100-100:
It is 1.

[0074]

EXAMPLES Next, specific synthesis examples of the compound of the present invention will be described.

Synthesis Example 1. Methyl N- [2-[(1,3
-Dimethyl-2-butenylidene) aminooxymethyl]
Synthesis of [phenyl] carbamate (Compound No. 13)

[1] 7.85 g of 4-methyl-3-penten-2-one, 6.67 g of hydroxylamine hydrochloride and 13.06 g of sodium acetate trihydrate were refluxed in 180 ml of methanol for 1 hour under reflux. Heated. After completion of the reaction, methanol was distilled off under reduced pressure, water was added to the residue, and then the mixture was extracted with ethyl acetate. Dried over anhydrous sodium sulfate,
The solvent was distilled off under reduced pressure to obtain 8.0 g of 4-methyl-3-penten-2-one oxime.

[2] 3.73 g of 4-methyl-3-penten-2-one oxime obtained in the above step [1] and 5.98 g of methyl N- [2- (chloromethyl) phenyl] carbamate were added to methylene chloride. To a solution dissolved in 35 ml, 33 ml of 2.2M aqueous sodium hydroxide solution at room temperature
And tetra-n-butylammonium hydrogen sulfate 11.
2 g was added and stirred for 10 minutes. Further, 35 ml of methylene chloride, 33 ml of 2.2M aqueous sodium hydroxide solution and 11.2 g of tetra-n-butylammonium hydrogen sulfate.
Was subsequently added and stirred for 1 hour. The reaction mixture was put into water, extracted with methylene chloride, washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent; methylene chloride: hexane = 4: 1) to obtain the desired product (compound N
o. 13) 1.65 g was obtained as a viscous liquid.

Synthesis Example 2. Methyl N- [2-[(1,3
-Dimethyl-2-butenylidene) aminooxymethyl]
Synthesis of Phenyl] -N- (methoxymethyl) carbamate (Compound No. 14)

A solution prepared by dissolving 1.38 g of the compound (Compound No. 13) obtained in Synthesis Example 1 in 20 ml of tetrahydrofuran was cooled to 0 ° C., and 0.24 g of 60% sodium hydride was added little by little. After that, the temperature was raised to room temperature. 0.48 g of chloromethyl methyl ether was added to this mixture at room temperature, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. The reaction mixture was put into water, extracted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent; hexane: ethyl acetate = 5: 1) to obtain 1.12 g of the desired product (Compound No. 14) as a viscous liquid.

Next, Table 1 shows representative examples of the compound of the present invention represented by the general formula (I).

[0081]

[Table 1]

[0082]

[Table 2]

[0083]

[Table 3]

[0084]

[Table 4]

[0085]

[Table 5]

Next, test examples of the compounds of the present invention as agricultural and horticultural fungicides will be described. The evaluation criteria were as follows, unless otherwise specified. [Evaluation Criteria] The control effect was obtained by visually observing the degree of disease of the test plant at the time of the investigation and determining the control index on the following five levels. [Control index] [Extent of disease] 5: No lesions are observed at all 4: Lesion area, number of lesions or lesion length is less than 10% of untreated section 3: Lesion area, lesion number or disease The spot length is less than 40% of the untreated section 2: The lesion area, the number of lesions or the lesion length is less than 70% of the untreated section 1: The lesion area, the number of the lesions or the lesion length is untreated 70% or more of ward

Test Example 1. Cucumber powdery mildew prevention effect test Cucumber (variety: four leaves) is cultivated in a plastic bowl with a diameter of 7.5 cm, and 10 ml of a chemical solution in which the active ingredient compound is adjusted to a predetermined concentration when the one-leaf stage is reached is used with a spray gun. Sprayed. After kept in a thermostatic chamber at 22 to 24 ° C. for about 24 hours, conidia of powdery mildew fungi were sprinkled and inoculated. Inoculation 10
After 11 days, the lesion area of the first leaf was investigated, and the control index was determined according to the evaluation criteria. Nos. 23 and 24 had a control index of 5 at 500 ppm, and compound No. 9,
29, 33, 34 and 53 have a control index of 4 at 500 ppm
Are shown respectively.

Test Example 2. Cucumber downy mildew prevention effect test Cucumber (variety: four leaves) is cultivated in a plastic bowl with a diameter of 7.5 cm, and 10 ml of a chemical solution in which the active ingredient compound is adjusted to a predetermined concentration when the second leaf stage is reached is sprayed using a spray gun. did. After keeping in a thermostatic chamber at 22 to 24 ° C. for about 24 to 48 hours, a spore suspension of downy mildew was spray-inoculated. Inoculation 7-1
After 2 days, the lesion area of the first leaf was investigated, and the control index was determined according to the above evaluation criteria. 1, 17 and 24 have a control index of 5 at 500 ppm, and compound N
o. 18 and 21 showed a control index of 4 at 500 ppm.

Test Example 3. Rice blast preventive effect test Rice (cultivar: Koshihikari) was cultivated in a plastic bowl with a diameter of 7.5 cm, and 20 ml of a chemical solution in which the active ingredient compound was adjusted to a predetermined concentration when the 4-leaf stage was reached was sprayed using a spray gun. . After being kept in a thermostatic chamber at 22 to 24 ° C for about 24 hours, a spore suspension of blast fungus was spray-inoculated. The number of lesions was examined 6 to 7 days after the inoculation, and the control index was determined according to the above evaluation criteria. 6, 9, 12, 30, 33, and 53 each showed a control index of 4 at 500 ppm.

Test Example 4. Oat crown rust preventive effect test Oat (cultivar: advance) was cultivated in a plastic bowl with a diameter of 7.5 cm, and 20 ml of a chemical solution in which the active ingredient compound was adjusted to a predetermined concentration when the 2-leaf stage was reached was used with a spray gun. Sprayed. After kept in a thermostatic chamber at 22 to 24 ° C. for about 24 hours, conidia of crown rust fungus were sprinkled and inoculated. Inoculation 11-1
After 3 days, the lesion area of the second leaf was investigated, and the control index was determined according to the above evaluation criteria. 6, 12,
30 and 34 have a control index of 5 at 500 ppm, and compound No. 14 and 46 each showed a control index of 4 at 500 ppm.

Test Example 5. Tomato epidemic preventive effect test Tomato (cultivar: Ponteroza) was cultivated in a plastic bowl with a diameter of 7.5 cm, and 10 ml of a chemical solution in which each test compound was adjusted to a predetermined concentration was sprayed using a spray gun when the 4-leaf stage was reached. . After keeping it in a constant temperature room at 22 to 24 ° C. for about 24 hours, it was spray-inoculated with a suspension of zoospores of Phytophthora infestans. Inoculation 3 ~
After 4 days, the lesion area was investigated and the control index was determined according to the above evaluation criteria. 23 and 29 are 50
Control index 5 at 0 ppm, and compound No. 19 is 5
A control index of 4 was shown at 00 ppm.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Shigeru Mitani 2-3-1 Nishishibukawa, Kusatsu City, Shiga Prefecture Central Research Laboratory, Ishihara Sangyo Co., Ltd. (72) Seiko Miyashita 2-3-3 Nishishibukawa, Kusatsu City, Shiga Prefecture No. 1 Ishihara Sangyo Co., Ltd. Central Research Laboratory

Claims (6)

[Claims] 1. A compound represented by the general formula (I): (In the formula, R ¹ is an optionally substituted alkyl group, and R 1
² is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or -COX ¹
A group, X ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or an optionally substituted alkoxy group, R ³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, R 3
⁴ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted phenyl group, a cyano group,- NR ⁵ R ₆ group or —CO
₂ R ⁷ groups, R ³ and R ⁴ may combine with each other to form a 4 to 7 membered ring with the adjacent carbon atom, R ⁵
And R ⁶ are each a hydrogen atom or an optionally substituted alkyl group, R ⁷ is an optionally substituted alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or a substituted Is an alkoxy group which may be substituted, except for the case where R ³ is an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and R ⁴ is an optionally substituted phenyl group). N-
Phenyl carbamate compounds. 2. A compound represented by the general formula (I): (In the formula, R ¹ is an optionally substituted alkyl group, and R 1
² is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or -COX ¹
A group, X ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or an optionally substituted alkoxy group, R ³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, R 3
⁴ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted phenyl group, a cyano group,- NR ⁵ R ⁶ group or —CO
₂ R ⁷ groups, R ³ and R ⁴ may combine with each other to form a 4 to 7 membered ring with the adjacent carbon atom, R ⁵
And R ⁶ are each a hydrogen atom or an optionally substituted alkyl group, R ⁷ is an optionally substituted alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or a substituted Is an alkoxy group which may be substituted, except for the case where R ³ is an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and R ⁴ is an optionally substituted phenyl group). N-
A pest control agent comprising a phenyl carbamate compound as an active ingredient. 3. A compound represented by the general formula (I): (In the formula, R ¹ is an optionally substituted alkyl group, and R 1
² is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or -COX ¹
A group, X ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or an optionally substituted alkoxy group, R ³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, R 3
⁴ is a hydrogen atom, an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkoxy group, an optionally substituted alkylthio group, an optionally substituted phenyl group, a cyano group,- NR ⁵ R ⁶ group or —CO
₂ R ⁷ groups, R ³ and R ⁴ may combine with each other to form a 4 to 7 membered ring with the adjacent carbon atom, R ⁵
And R ⁶ are each a hydrogen atom or an optionally substituted alkyl group, R ⁷ is an optionally substituted alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or a substituted Is an alkoxy group which may be substituted, provided that R ³ is an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and R ⁴ is an optionally substituted phenyl group). N-
A method for producing a phenylcarbamate compound, which comprises a compound represented by the general formula (II): (In the formula, R ² , R ³ , R ⁴ and A are as described above.)
Or a salt thereof and a general formula of ClCO ₂
A method for producing the N-phenylcarbamate compound, which comprises reacting with a compound represented by R ¹ (wherein R ¹ is as described above). 4. A compound represented by the general formula (I-2): (In the formula, R ¹ is an optionally substituted alkyl group, and R 1
³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, and R ⁴ is hydrogen. Atom, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted alkoxy group, optionally substituted alkylthio group, optionally substituted phenyl group, cyano group,-
NR ⁵ R ⁶ group or —CO ₂ R ⁷ group, and R ³ and R ^4
May combine with each other to form a 4- to 7-membered ring with the adjacent carbon atom, R ⁵ and R ⁶ are each a hydrogen atom or an optionally substituted alkyl group, and R ⁷ is optionally substituted. A good alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or an optionally substituted alkoxy group, provided that R ³ is an optionally substituted alkyl group or an optionally substituted alkyl group. A cycloalkyl group and R ⁴ is a phenyl group which may be substituted), the process for producing an N-phenylcarbamate compound represented by the following general formula (III): Reacting the compound represented by the formula (wherein R ³ , R ⁴ and A are as described above) with the compound represented by the general formula R ¹ OH (wherein R ¹ is as described above). The method for producing the N-phenylcarbamate compound, which comprises: 5. A compound represented by the general formula (I-3): (In the formula, R ¹ is an optionally substituted alkyl group, and Y 1
Is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or a -COX ¹ group, X ¹
Is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group or an optionally substituted alkoxy group, and R ³ is substituted. An optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, R ⁴ is a hydrogen atom,
Optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted alkoxy group, optionally substituted alkylthio group, optionally substituted phenyl group, cyano group, -NR ⁵ R ⁶ group Or a —CO ₂ R ⁷ group, R ³ and R ⁴ may be bonded to each other to form a 4- to 7-membered ring with an adjacent carbon atom, and R ⁵ and R ⁶ are each a hydrogen atom or a substituted one. An optionally substituted alkyl group, R ⁷ is an optionally substituted alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or an optionally substituted alkoxy group, provided that R 7 ³ is an optionally substituted alkyl group or an optionally substituted cycloalkyl group, and R ⁴ is an optionally substituted phenyl group). A method for producing a compound, comprising the formula (I-
2) [Chemical 8] (In the formula, R ¹ , R ³ , R ⁴ and A are as described above.)
And a compound represented by the general formula Y-W (wherein Y is as described above and W is a chlorine atom, a bromine atom or an iodine atom), and the above-mentioned N is reacted. -A method for producing a phenylcarbamate compound. 6. A compound represented by the general formula (I-2): (In the formula, R ¹ is an optionally substituted alkyl group, and R 1
³ is an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted alkenyl group, an optionally substituted cycloalkenyl group or an optionally substituted alkynyl group, and R ⁴ is hydrogen. Atom, optionally substituted alkyl group, optionally substituted cycloalkyl group, optionally substituted alkoxy group, optionally substituted alkylthio group, optionally substituted phenyl group, cyano group,-
NR ⁵ R ⁶ group or —CO ₂ R ⁷ group, and R ³ and R ^4
May combine with each other to form a 4- to 7-membered ring with the adjacent carbon atom, R ⁵ and R ⁶ are each a hydrogen atom or an optionally substituted alkyl group, and R ⁷ is optionally substituted. A good alkyl group, A is a hydrogen atom, a halogen atom, an optionally substituted alkyl group or an optionally substituted alkoxy group, provided that R ³ is an optionally substituted alkyl group or an optionally substituted alkyl group. A cycloalkyl group and R ⁴ is a phenyl group which may be substituted), the process for producing an N-phenylcarbamate compound represented by the general formula (IV): (Wherein R ¹ and A are as described above, and W is a chlorine atom, a bromine atom or an iodine atom) and a compound represented by the general formula H-O-N = CR ³ R ⁴ (wherein R is ³ and R ⁴
Is as described above) is reacted with the compound represented by the above. The method for producing the N-phenylcarbamate compound described above.