WO1998002414A1

WO1998002414A1 - N-phenylcarbamate compounds, process for preparing the same, and agricultural and horticultural bactericides

Info

Publication number: WO1998002414A1
Application number: PCT/JP1997/002417
Authority: WO
Inventors: Masanori Watanabe; Toshinobu Tanaka; Shin Suizu; Takehiko Asahara
Original assignee: Ube Industries, Ltd.
Priority date: 1996-07-12
Filing date: 1997-07-11
Publication date: 1998-01-22
Also published as: JPH1025278A

Abstract

N-Phenylcarbamate compounds represented by formula (1), wherein R1 represents a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or -CO¿2R?4 wherein R4 represents an alkyl group having 1 to 4 carbon atoms; R2 represents an alkyl group having 1 to 4 carbon atoms; R3 represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, a haloalkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, or a nitro group; and n is an integer of 1 to 5.

Description

Specification

N-phenyl carbamate compound, its production method and fungicide for agricultural and horticultural use

Technical field

The present invention relates to a novel N-phenylcarbamate compound useful as a fungicide for pus horticulture.

Conventional technology

It is known that certain N-phenyl carbamate compounds have bactericidal activity (for example, W093- 3504, JP-A-5-170726, Japanese Unexamined Patent Application Publication No. Hei 6-5-67556, Japanese Unexamined Patent Publication No. Hei 6-271715, Japanese Unexamined Patent Publication No. Hei 6-34007, and Japanese Unexamined Patent Publication No. Hei 7-145137. ).

However, those N-phenyl carbamate compounds cannot be said to have sufficient bactericidal activity. For this purpose, compounds having more excellent bactericidal activity are required.

The present inventors have conducted studies to solve the above-mentioned problems, and as a result, have found that a novel N-phenylcarbamate compound represented by the following general formula (1) has excellent bactericidal activity. The invention has been completed. Disclosure of the invention

That is, the present invention is as follows.

The first invention has the following formula (1):

In the formula, R ¹ is a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, number 3-5 alkenyl group or C - C0 ₂ R ⁴ represents; in here, R ⁴ represents a Sumifukuro number 1-4 alkyl groups; R ² is 1-4 alkyl group having a carbon number R ³ represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, and a carbon atom having 1 to 4 carbon atoms. Represents four haloalkoxy groups, an alkylthio group having 1 to 4 carbon atoms, or a nitro group; and π represents an integer of 1 to 5, and represents an N-phenylcarbamate compound derivative (compound ( 1))).

In the second invention, the formula (2)

In the formula, R ² has the same meaning as described above; X is a chlorine atom or a bromine atom; a compound represented by the following formula (compound (2)):

The following equation (3):

Wherein, 1¾ ³ and门have the same meanings as defined above,

Wherein the compound represented by the formula (1) is reacted with a compound represented by the following formula (1):

Wherein, R ^2, 8 ^3, and (1 is the same as defined above,

The present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-a)) represented by

A third invention relates to the above compound (1-1a)

The following equation (4):

R ^r -Y (4)

In the formula, R ¹ ′ is an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms or one C 0 ₂ represents R ⁴ ; wherein represents an alkyl group having 1 to 4 carbon atoms; and Y represents a chlorine atom, a bromine atom,

Wherein the compound represented by the formula (1) is reacted with a compound (compound (4)) represented by the following formula (1b):

Wherein R ¹ ′, R ² , ³ and 1 ^ are as defined above,

The present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-b)) represented by

The fourth invention is

The following equation (5):

In the formula, R ¹ represents an alkoxy group having 1 to 4 carbon atoms; R ² and X are as defined above,

Wherein the compound represented by the formula (1) is reacted with the compound represented by the formula (3), wherein the compound represented by the formula (3) is represented by the following formula (11-C):

Wherein R ′, R ² , R ³ and n are as defined above,

The present invention relates to a method for producing an N-phenyl carbamate compound (compound (1-c)) represented by

The fifth invention relates to a fungicide for agricultural and horticultural use containing the compound (1) as an active ingredient. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the present invention will be described in detail.

R ′ to R ⁴ represented by the novel N-phenyl carbamate compound as the target compound and the raw material for producing the compound are as follows.

(R ')

R ′ is a hydrogen atom, an alkoxy group having 4 to 4 carbon atoms, an alkyl group having 4 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms can 3-5 alkenyl group or a carbon C0 ₂ R ⁴ is exemplified, this Here, R ⁴ represents an alkyl group having 4 to 4 carbon atoms. Examples of the alkyl group include a linear or branched one, and preferably CH ₃ .

The alkoxy group, there may be mentioned a straight or branched, good Mashiku is _{_{_{CH 3 0, C 2 H 5}}} 0.

Examples of the alkyl group include a linear or branched one, and preferably C ₂ H _S.

Examples of the alkynyl group include straight-chain or branched ones, and preferably HC≡CCH ₂ .

Arco The alkoxyalkyl group, although Ru may be mentioned a straight or branched, preferably Flip 1 "1 ₃ 0_Rei_1 ~ 1 ₂ Dearu.

Examples of the alkenyl group include a linear or branched alkenyl group, and preferably CH ₂ CHCHCH ₂ .

(R ')

Examples of R ′ include the same alkyl group, alkenyl group, alkynyl group, alkoxyalkyl group and —CO ₂ R ⁴ (R ⁴ has the same meaning as described above) as described for R ¹ .

(R ")

The R ", include the same alkoxy groups as mentioned in R ^1.

( ² )

Examples of R ² include an alkyl group having 1 to 4 carbon atoms.

The alkizole group may be a straight-chain or branched one, and is preferably CH ₃ or C ₂ H ₅ .

(R ³ )

R ³ includes a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. A haloalkoxy group, an alkylthio group having 1 to 4 carbon atoms and Can be mentioned.

Examples of the halogen atom include a chlorine atom, an iodine atom, an iodine atom, and a fluorine atom.

The substitution position of the halogen atom is not particularly limited.

Examples of the alkyl group include straight-chain or branched ones, and preferably CH ₃ , C ₂ H ₅ or C ₃ H ₇ .

The substitution position of the alkyl group is not particularly limited, but is preferably a 3-, 4- or 5-position.

The haloalkyl group, linear or branched, chlorine脤子, iodine IS element, there may be mentioned those having a hard mouth Gen atoms, such as the back MotoHara element and fluorine atoms, the good Mashiku CF ₃ It is.

The substitution position of the haloalkyl group is not particularly limited.

The substitution position of the cyano group is not particularly limited, but is preferably 3- or 4-position.

Examples of the alkoxy group include a linear or branched alkoxy group, preferably OCH ₃ or OC ₂ H ₅ .

The substitution position of the alkoxy group is not particularly limited, but is preferably a 3-, 4- or 5-position.

The haloalkoxy group, there may be mentioned a straight or branched, preferably a _{_{OCF 3, OC F 2 CH F}} 2 or OC F ₂ CH FC F _3. The g-position of the haloalkoxy group is not particularly limited, but is preferably a 4-position.

Examples of the alkyl group include straight-chain or branched ones, and preferably S CH ₃ .

The substitution position of the alkylthio group is not particularly limited, but is preferably the 3-position. The substitution position of the amino group is not particularly limited, but is preferably the 3-position. (n)

n can be an integer of 1 to 5, preferably 1, 2, 3 or 5.

Examples of the compound (1) include those obtained by combining the above-mentioned various substituents. Preferred compounds from the viewpoint of medicinal effects are as follows.

(1) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) is a hydrogen atom.

(2) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _π is a halogen atom.

(3) R ′ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkynyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a halogen atom.

(4) R ¹ is an alkoxyalkyl group having 2 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a halogen atom.

(5) R ¹ is 1-4 alkoxy group having a carbon number, R ² is alkyl Le group number〗 to ⁴ _carbons, (R ³⁾ π is an alkyl group of one to four carbon atoms some stuff.

(6) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a haloalkyl group having 1 to 4 carbon atoms. some stuff.

(7) R 'is § Li alkynyl group having 3-5 carbons, R ² is alkyl Le group having ¹ to ⁴ _carbon, (R ³⁾ η is C 1-4 haloalkyl group having a carbon What is.

(8) R ¹ is an alkoxyalkyl group number 2-5 carbons, 8 ² is 1 to 4 alkyl groups having a carbon number, (R ³⁾ _eta is a haloalkyl group having〗 to 4 carbons some stuff.

(9) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a cyano group.

(10) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is an alkoxy group having 1 to 4 carbon atoms. some stuff.

Π1) R ¹ is a hydrogen atom, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η Is alkoxy having 1 to 4 carbon atoms.

(12) R ¹ is an alkenyl group having 3 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _n is an alkoxy group having 1 to 4 carbon atoms. some stuff.

(13) R ¹ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _π is an alkoxy group having 1 to 4 carbon atoms thing.

(14) R ¹ is an alkoxyalkyl group having 2 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is an alkoxy group having 4 to 4 carbon atoms thing.

(15) gar (a 0 ₂ 1¾ ⁴ Deari, alkyl group R ² is a 1 to 4 carbon atoms,

(R ³ ) _π is alkoxy having 1 to 4 carbons.

(16) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _π is a haloalkoxy group having 1 to 4 carbon atoms. What is.

(17) R ¹ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkynyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a haloalkoxy group having 1 to 4 carbon atoms. What is.

(18) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) is an alkylthio group.

(19) R ′ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ). Are the two groups.

As R ¹ to R ³ and n of the compound (1) represented by (1) to (19) comprising these preferred combinations, the preferred ones described in the above description and the more preferred ones can be exemplified. .

Preferred specific examples of these compounds (1) are compounds 1, 3, 5, 6, 8 to 14, 16, 16, 18 to 21, 23, 25 to 25 shown in Table 1 below. 27, 29-33, 35-37, 39-45, 47, 49, 51, 53, 55, 57-62 and 64.

Compound (1) can be synthesized by the following synthesis methods 1 to 3. (Synthesis method 1) Compound (1-1a) (compound (1) in which R ¹ is a hydrogen atom) is produced by reacting compound (2) with compound (3) in a solvent as shown below. This reaction can be accelerated in the presence of a base.

(1-a)

In the formula, R ¹ , R ² , R ³ , n and X are as described above.

The reaction step is usually performed in the presence of a solvent and a base.

The type of the solvent is not particularly limited as long as it does not directly participate in the reaction, and examples thereof include alcohols such as isopropanol, t-butanol, and diethylene glycol; and ketones such as acetone, methyl ethyl ketone, and cyclohexanone. Aliphatic hydrocarbons such as n-hexane and cyclohexane; ethers such as getyl ether, diisopropyl ether, tetrahydrofuran, and dichlorohexane; dichloroethane, chloroform, carbon tetrachloride, tetra Halogenated hydrocarbons such as chloroethane; aromatic hydrocarbons such as benzene, chlorobenzene, toluene, xylene; ditolyls such as acetonitrile and propionitrile; dimethylformamide, dimethylsulfoxide And polar solvents such as sulfolane; and A mixture of these solvents and the like can be mentioned.

The amount of the compound (2) and the compound (3) to be used is preferably in a molar ratio of (1:10) to (10: 1), and more preferably (1: 3) to (3: 1). Range. The amount of the solvent used may be such that the compound (3) is used in an amount of 0.1 to 80% by weight; preferably 0.1 to 40% by weight.

As the base, an inorganic base and an organic base can be used, and an organic base is preferable.

Examples of the inorganic base include sodium carbonate, potassium carbonate, calcium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, calcium hydroxide, and other alkaline metal or alkaline earth metal carbonates. And hydroxides; and hydrides of alkali metals such as lithium hydride and sodium hydride.

Examples of the organic base include alkoxides of alkali metal atoms such as sodium methoxide and potassium t-butoxide, getylamine, triethylamine, and pyridine.

The amount of the base to be used is 0.01 to 5 moles, preferably 0.8 to 2 moles, per 1 mole of Compound (3).

The reaction temperature is in the range from 140 to the boiling point of the solvent used, preferably from 0 to 7.

The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.5 to 24 hours, preferably 1 to 10 hours.

Compound (2) can be synthesized according to the method described in JP-A-6-340607.

The compound (3) can be obtained by reacting an amide with a sulfur-containing reagent (eg, pentasulfide or Lawson's reagent) according to the method described in JP-A-6-92929.

After completion of the reaction, the target compound (〗一 a) shown in Table 1 described below produced as described above is subjected to ordinary post-treatments such as extraction, leaching, filtration and the like. It can be appropriately purified by known means such as recrystallization and various types of chromatography.

(Synthesis method 2) Compound (〗 _b) (where R ¹ in compound (1) is an alkyl group having 4 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, and 2 to 5 carbon atoms Is an alkoxyalkyl group or 1 C0 ₂ R ⁴ (where R ⁴ represents an alkyl group having 1 to ⁴ carbon atoms.) Is a compound represented by the following formula. It can be produced by reacting the product (4). This reaction can be facilitated in the presence of a base. Also, a catalyst can be used if necessary.

n

(1 -b)

In the formula, R ¹ ′, R ² , R ³ , n, X and Y are as defined above.

The type of the solvent is not particularly limited as long as it does not directly participate in the present reaction, and examples thereof include those described in Synthesis Method 1.

The amounts of compound (1 -a) and compound (4) used are (1 _: 20) to (10

: 1), and more preferably (1: 10) to (1: 1).

Use of the solvent S can be used such that the amount of the compound (化合物 a) is from 0.1 to 80% by weight; preferably, from 0.1 to 40% by weight.

Examples of the base include those described in Synthetic Method 1, and are preferably inorganic bases.

The amount of the base used is 0.001 to 5 times mol based on compound (1-a), 0.8 to 2 moles is preferable.

The reaction temperature is in the range of from 140 ° C to the boiling point of the solvent to be used, preferably from 110 to 70 ° C.

Examples of the catalyst include benzyl triethylammonium chloride and π-butylammonium bromide tetral.

The amount of the catalyst to be used is from〗 to 20% by weight, preferably from 3 to 10% by weight, based on the weight of compound (1-a).

The reaction time varies depending on the above-mentioned concentration and temperature, but is usually from instant to 12 hours, preferably 0.5 to 8 hours.

As the compound (4), a commercially available product can be used.

After completion of the reaction, the target compound (1 -b) produced as described in Table 1 below is subjected to ordinary post-treatments such as extraction, concentration, and filtration, and then re-used as necessary. It can be appropriately purified by known means such as crystals and various types of chromatography.

(Synthesis method 3)

Compound (1-1c) (compound in which R ¹ in compound (1) is an alkoxy group having 1 to 4 carbon atoms) is prepared by compound (3) and compound (5) in a solvent as shown below. It can be produced by reacting. This reaction is facilitated by the presence of a base.

(1 -c) In the formula, R′R ² , R ³ , n and X are as defined above.

The amounts of compound (5) and compound (3) used are preferably in a molar ratio of (1:10) to (10: 1), more preferably (〗: 3) to (3:〗). Range.

The solvent may be used in such an amount that the compound (5) is contained in an amount of 0.1 to 80% by weight; preferably 0.1 to 40% by weight.

Examples of the base include those described in Synthesis Method II, and are preferably organic bases.

The amount of the base to be used is 001 to 5 moles, preferably 0.8 to 2 moles, relative to compound (5).

The reaction temperature is in the range of from 40 ° C to the boiling point of the solvent used, preferably from 110 to 70 ° C.

The reaction time varies depending on the above-mentioned concentration and temperature, but is usually 0.5 to 24 hours, preferably〗 to 10 hours.

Compound (5) can be converted to N-2-methylphenylhydroxylamine through 2-toluene toluene according to the method described in JP-A-6-340607, for example, as shown below. CI C0 _² R ₂ (wherein, R ² has the same meaning as defined above) in which after the reaction in the presence of a base, such as by O- alkyl turned into alkyl halides, with further N- halosuccinimide Specifically, it can be synthesized by ordinary halogenation reaction by ordinary chlorination using N-chlorosuccinimide (NCS) or ordinary bromination using N-promosuccinimide (NBS).

After completion of the reaction, the target compound (11-C) shown in Table 1 described below, produced as described above, is subjected to ordinary post-treatments such as extraction, concentration, filtration, and the like, if necessary. It can be appropriately purified by known means such as crystals and various types of chromatography. (Effect of controlling pathogenic bacteria)

Examples of the pathogens of agriculture in which the compound (1) of the present invention has a controlling effect include rice blast, cucumber and disease, barley powdery mildew, wheat leaf rust and the like.

(Agricultural and horticultural pesticides)

The agricultural and horticultural fungicide of the present invention contains at least one compound (1) as an active ingredient.

The compound (1) can be used alone, but it is usually compounded with a carrier, a surfactant, a dispersant, an auxiliary agent and the like (for example, powders, emulsions, fine granules, granules, water, etc.). Prepared as a composition such as a wetting agent, an oily suspension, or an aerosol).

Carriers include, for example, solid carriers such as talc, bentonite, clay, kaolin, cadmium earth, white carbon, vermiculite, slaked lime, cake sand, ammonium sulfate and urea; hydrocarbons (kerosene, mineral oil, etc.), aromatics Hydrocarbons (benzene, toluene, xylene, etc.), chlorinated hydrocarbons (chloroform, carbon tetrachloride, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, cyclohexanone, isophorone, etc.) ), Liquid carriers such as esters (ethyl acetate, ethylene glycol acetate, dibutyl maleate, etc.), alcohols (methanol, n-hexanol, ethylene glycol, etc.), polar solvents (dimethylformamide, dimethyl sulfoxide, etc.) and water; Air, nitrogen Gaseous carriers, such as (in this case, can be mixed jet) carbon dioxide and Freon or the like can be a is given.

Examples of surfactants and dispersants that can be used to improve the performance of this drug, such as adhesion to animals and plants, improved absorption, sensitivity of drugs, emulsification, and spreading, include alcohol sulfates and alkyls. Sulfonates, ligninsulfonates, polyoxyethylene render alcohols and the like can be mentioned. And the properties of the formulation For improvement, for example, carboxymethylcellulose, polyethylene glycol, gum arabic and the like can be used as adjuvants.

In the production of the present agent, the above-mentioned carrier, surfactant, dispersant, and auxiliary can be used alone or in appropriate combination, respectively, according to the respective purposes.

When the compound (1) of the present invention is formulated, the active ingredient is usually 1 to 50% by weight for emulsions, usually 0.3 to 25% by weight for powders, usually 1 to 90% by weight for wettable powders, and 1 to 90% by weight for granules. It is usually 0.5 to 10% by weight, for oils it is usually 0.5 to 5% by weight, and for azole it is usually 0.5 "to 5% by weight.

These preparations can be diluted to an appropriate concentration and sprayed on the surface of plants, leaves, soil, or paddy fields, or applied directly for various purposes, depending on the purpose. Example

Next, specific examples of the present invention will be described. Note that the present invention is not limited to these.

Example 1 (Synthesis of Compound (1))

(1) Synthesis of methyl N— [2 -— [cyclobutyral pill (4-methoxyphenylimino) methyl] methylmethylphenyl] caprate (compound 27)

Cyclopropylcarboxy-41-methoxyanilide (2.0 g) dissolved in tetrahydrofuran (15 ml) was added to potassium t-butoxide (0.14 g), N- [2- (chloromethyl ) was added phenyl] force Rubameto the (1. 9 g) at room temperature and stirred for 1 hour at 50 ^e C. After completion of the reaction, the reaction solution was poured into 20 ml of water, extracted with ethyl acetate, washed with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue is subjected to silica gel chromatography.

(ヮ -gel C-200, toluene: ethyl acetate = 9: 1 elution) to obtain 2.7 g of the target substance as a pale yellow powdery solid. (2) Synthesis of methyl N- [2- [cyclopropyl (4-methoxyphenylimino) methyl] thiomethylphenyl] -N-propargylcaprate (Compound 32)

Methyl N- [2- (cyclopropyl (4-methoxyphenylimino) methyl] thiomethylphenyl] dissolved in tetrahydrofuran (8 ml)

(0.65 g), potassium hydroxide powder (85%) (0.23 g), tetra-n-butylammonium bromide (0.05 g) and propargyl iodide (0.37 g) in a chamber After the addition, the mixture was stirred at the same temperature for 1 hour. After the reaction is completed, the reaction solution is

The mixture was poured into I, extracted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel chromatography (ヮ -gel C-200, toluene: ethyl acetate = 19: 1 elution) to obtain 0.67 g of the target compound as a pale yellow viscous oil. Was.

(3) Methyl N- [2- [cyclopropyl (4-trifluro-methoxyphenylimino) methyl] -methyl-phenyl] -N- (methoxy) caprate

Synthesis of (Compound 39)

Cyclopropylcarbothioate 4-fluorotrifluoromethoxyanilide (0.35 g) dissolved in tetrahydrofuran (8 ml) was added to potassium t-butoxide (0.18 g), N— [2— (Promomethyl) phenyl] mono-N-methoxycarbamate

(0.37 g) was added at room temperature, and the mixture was stirred at the same temperature for 1 hour. After completion of the reaction, the reaction solution was poured into water (15 ml), extracted with ethyl acetate, washed with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography (Pecogel C-200, toluene: ethyl acetate = 19: 1 elution) to obtain 0.4 g of the target substance as a yellow viscous oil.

(4) Synthesis of other compounds (1) in Table 1

Other compounds (1) in Table 1 below were synthesized according to the methods described in (1) to (3) above. table 1

Table 1 (continued)

Table 1 (continued)

Example 2 (Physical properties of compound (1))

The H-NMR (CDC I <5 value, p pm) of the compound (表) in Table 1 is as follows.

(Compound 1)

0.62-1.21 (m, 4H), 1.70-1.85 (bs, 1H), 3.73 (s, 3H), 3.76 (s, 3H), 4.32 (s, 2H), 6.84

(d, 2 H), 7.00-7.09 (m, 1 H), 7.2 1 -7. 38 (m, 5 H), 7.49-7.6 1 (m, 1 H)

(Compound 3)

0.70- 1.14 (m, 4 H), 1.65-1.82 (b s, 1 H), 3.7

3 (s, 3H), 3.76 (s, 3H), 4.29 (s, 2H), 6.77 (d, 2H), 7.18-7.41 (m, 5 H), 7.46-7.57 (m, 1

H)

(Compound )

0.70-1.12 (m, 4H), 1.20 (t, 3H), 1.68-1.82 (bs, 1H), 3.76 (s, 3H), 3 96 (q, 2H), 4.32 (s, 2H), 6.79 (d, 2H), 7.15-7.39 (m, 5H), 7.

45- 7.60 (m, 1 H)

(Compound 5)

0.66-1.27 (m, 4H), 1.63-1.84 (bs, 1H), 2.28 (s, 1H), 3.64 (s, 3H), 3 70- 4.73 (m, 4 H), 6.60-6. 89 (m, 2 H), 7.2 1 -7. 56 (m, 6 H)

(Compound 6)

0.70-1.17 (m, 4H), 1.67-1.82 (bs, 1H), 3.4

5 (s, 3H), 3.66 (s, 3H), 4.17 (dd, 2H), 4.64 (d, 1H), 5.06-5.31 (m, 1 H), 6.79 (d, 2H), 7. 1 2— 7. 36 (m, 5 H), 42-7.5 1 (m, 1 H)

(Compound 8)

0.72-1.18 (m, 4H), 1.65-1.80 (bs, 1H), 3.72 (s, 3H), 3.77 (s, 3 H), 4.30 (s, 2H), 6.72

(d, 2H), 7.20-7.57 (m, 6H)

(Compound 9)

0.70-1.13 (m, 4H), 1.21 (t, 3H), 1.63-1.82

(b s, 1 H), 3.77 (s, 3 H), 3.97 (q, 2 H), 4.30

(s, 2H), 6.61-6.79 (m, 2H), 7.21-7.32 (m, 3H), 7.37-7.43 (m , 2 H), 7.49- 7.59 (m, 1 H)

(Compound 10)

0.65-1.20 (m, 4H), 1.65-1.85 (bs, 1H), 2.28 (s, 1H), 3.65 (s, 3H ), 3.72-4.72 (m, 4H), 6.60-6.80 (m, 2H), 7.24-7.54 (m, 6H)

(Compound 11)

0.67-1.17 (m, 4H), 1.64-1.85 (bs, 1H), 3.72 (s, 3H), 3.77 (s, 3 H), 4.29 (s, 2H), 6.61

(d, 2 H), 7.25-7.39 (m, 3 H), 7.47-7.69 (m, 3 H)

(Compound 1 2)

0.66-1.19 (m, 4H), 1.74-1.95 (m, 1H), 2.32

(s, 3H), 3.74 (s, 3H), 3.76 (s, 3H), 4.30 (s, 2H), 6.61-6.84 (m, 2 H), 7.2 2-7.38 (m, 5 H), 7.47-7.6 1 (m, 1 H)

(Compound 13)

0.70-1.10 (m, 4H), 1.25 (d, 6H), 1.76-1.93 (bs, 1H), 2.79- 2.96 (m, 1H), 3.74 (s, 3H),

3.77 (s, 3 H), 4.31 (s, 2 H), 6.79 (d, 2 H), 7.17 (d, 2H), 7.20-7.39 (m, 3 H), 7.48- 7.60

(m, 1 H)

(Compound 14)

0.66-1.35 (m, 1 H), 1.77-1.97 (m, 1 H),

2.79-2.95 (m, 1 H), 3.76 (s, 3 H), 3.97 (q, 2 H), 4.32 (s, 2 H), 6.79 (d, 2 H), 7.17 (d,

2 H), 7.23-7.37 (m, 3H), 7.48-7.61 (m, 1H) (compound 15)

0.73 -0.87 (m, 2H), 1.00-1.15 (m, 2H), 1.62-1.78 (bs, 1H), 3.72 (s, 3H) ), 3.77 (s, 3H),

4.32 (s, 2 H), 6.83 (d, 1 H), 7.06-7.14 (m,

1H), 7.28—7.36 (m, 3H), 7.40-7.49 (m, 1H), 7.50-7.59 (m, 1H), 7.61 (d, 1 H)

(Compound 16)

0.70-1.22 (m, 4H), 1.60-1.82 (bs, 1H), 3.7

3 (s, 3H), 3.77 (s, 3H), 4.31 (s, 2H), 6.91-7.13 (m, 2H), 7.28-7 . 60 (m, 6 H)

(Compound 18)

0.72-0.90 (m, 2 H), 0.98-1.14 (m, 2 H), 1.21 (t, 3 H), 1.6 1-1.84 (bs , 1 H), 3.76 (s, 3 H),

3.97 (q, 2 H), 4.32 (s, 2 H), 6.90 (d, 2 H), 7.25-7.38 (m, 3 H), 7.49-7. 64 (m, 3H)

(Compound 19)

0.74-0.87 (m, 2H), 1.00—1.12 (m, 2H), 1.63 -1.80 (bs, 1 H), 3.73 (s, 3 H), 3.77 (s, 3 H), 4.30 (s, 2 H), 6.90 (d, 2 H) , 7.28- 7.38 (m, 3 H), 7.49- 7.59 (m, 3 H)

(Compound 20)

0.70-1.15 (m, 4H), 1.60-1.83 (bs, 1H), 2.2

8 (s, 1 H), 3.55—3.86 (m, 3.8 H), 4.02-4.30 (m, 4 H), 4.48-4.60 (m, 1. 2 H), 6.92 (d, 2 H) ''

7.27-7.40 (m, 3H), 7.45-7.62 (m, 3H)

(Compound 21)

0.70-0.80 (m, 2 H), 0.95-1-1.7 (m, 2 H), 1.62-1.84 (bs, 1 H), 3.46 (s, 3 H), 3.65 (s, 3H), 4.20 (dd, 2H), 4.65 (d, 1H), 5.10-5.30 (m, 1H), 6. 92 (d, 2 H), 7.24 to 7.34 (m, 3H), 7.42 to 7.50 (m, 1 H), 7.52 to 7.60 (m, 2 H)

(Compound 23)

0.76-0.92 (bs, 2H), 1.00-1.15 (bs, 2H), 1.60-1.76 (bs, 1H), 3.73 (s, 3H ), 3.78 (s, 3H), 4.30 (s, 2H), 7.01-7.13 (m, 2H), 7.29—7.43 (m, 5H), 7.47- 7.54 (m, 1 H)

(Compound 24)

0.68- 1.22 (m, 4 H), 1.58- 1.80 (b s, 1 H), 2.2

9 (s, 1 H), 3.66 (s, 3 H), 3.72-4.73 (m, 4H), 6.97-7.54 (m, 8 H)

(Compound 25)

0.79-0.88 (m, 2H), 1, 02-1.1 1 (m, 2H), 1.60 — 1.77 (bs, 1H), 3.73 (s, 3H) , 3.77 (s, 3 H), 30 (s, 2 H), 6.89 (d, 2 H), 7.29-7.36 (m,

3 H), 7.47-7.55 (m, 1 H), 7.59 (d, 2 H)

(Compound 26)

70-1.21 (m, 4H), 1.73-1.91 (bs, 1H), 3 (s, 3H), 3.76 (s, 3H), 3.80 (s , 3H), 4.31 (s, 2H), 6.32-6.49 (m, 2H), 6.61 (dd, 1H) 7.14-7.37 (m, 4 H), 7.50-7.61 (m, 1 H)

(Compound 29)

0.69- 1.20 (m, 4H), 1.77-1.97 (m, 1H), 3.75 (s, 3H), 3.77 (s, 3H), 3. 80 (s, 3H), 4.30 (s, 2H), 6.69-6.91 (m, 4H), 7.20-7.38 (m, 3H), 7.46 -7.60 (m, 1 H)

(Compound 30)

0.68-1.12 (m, 4H), 1.17 (t, 3H), 1.78-1.99 (m, 1H), 3.30-3.97 (m, 4H) 5H), 3.80 (s, 3H), 4.19 (dd, 2H), 6.69—6.93 (m, 4H), 7.05-7.16 (m, 1 H), 7.22-7.32 (m, 2 H), 7.42-7.58 (m, 1 H)

(Compound 31)

0.70-1.24 (m, 4H), 1.77-1.97 (m, 1H), 3.64 (s, 3H), 3.71-3.98 (m, 4H) ), 4.18 (dd, 2H), 4.38-4.56 (m, 1H), 5.03-5.17 (m, 2H), 5.85-1. m, 1 H), 6.68-6.95 (m, 4 H), 7.05-7. 32 (m, 3 H), 7.4 1-7.57 (m, 1 H)

(Compound 32)

0.65-1.29 (m, 4H), 16-1.98 (m, 1H), 2.28 (s, 1 H), 3.66 (s, 3 H), 3.80 (s, 3 H), 4.00—4.73 (m, 4 H), 6.65-6.93 (m , 4 H), 7.1 7-7.39

(m, 3 H) '7.43-7.57 (m, 1 H)

(Compound 33)

0.7 1-1.22 (m, 4H), 1.74 1 2.07 (m, 1H), 3.45

(s, 3H), 3.67 (s, 3H), 3.80 (s, 3H), 4.08-.28 (m, 2H), 4.60-5.34 (m, 2 H), 6.62-6.95

(m, 4H), 7.1 2-7. 34 (m, 3H), 7.40-7.55 (m, 1H)

(Compound 34)

0.65-1.45 (m, 4H), 1.75-1.98 (m, 1H), 3.43

(s, 3H), 3.80 (s, 3H), 3.96-4.30 (m, 4H), 4.64 (d, 1H), 5.05-5.32 ( m, 1 H), 6.65-6.93

(m, 4 H), 7.10-7.32 (m, 3 H), 7.41 -7.54 (m, 1 H)

(Compound 35)

0.68- 1.23 (m, 4H), 1.76-1.91 (m, 1H), 3.60-1.85 (m, 9H), 4.17 (s , 2H), 6.69-6.91 (m, 4 H), 7.20-7.38 (m, 3 H), 7.43-7.53 (m, 1 H)

(Compound 36)

0.68- 1.20 (m, 4H), 1.41 (t, 3H), 1.78- 1.98

(m, 1H), 3.75 (s, 3H), 3.77 (s, 3H), 4.01 (q, 2H), 4.32 (s, 2H), 6. 69-1 6.91 (m, 4H), 7.24-7.38 (m, 3H), 7.48-7.61 (m, 1H)

(Compound 37)

0.67- 1.10 (m, 4 H), 1.2 1 (t, 3 H), 1.4 1 (t, 3 H), 1.76- 1.98 (m, 1 H), 3.77 (s, 3 H), 3.86- 4.08 (m, 4 H), 4.33 (s, 2 H) ), 6.69-6.91 (m, 4H), 7.24 to 7.38 (m, 3H), 7.45 to 7.60 (m, 1H) (compound 39)

0.70- 1.15 (m, 4H), 1.68-1.82 (m, 1H), 3.73 (s, 3H), 3.76 (s, 3H), 4. 30 (s, 2 H), 6.83 (d,

2 H), 7.05-7.38 (m, 5H), 7.46-7.60 (m, 1 H) (Compound 40)

0.70- 1.15 (m, 4H), 1.20 (t, 3H), 1.66-1.82 (bs, 1H), 3.75 (s, 3H), 3 97 (q, 2H), 4.31 (s, 2H), 6.83 (d, 2H), 7.16 (d, 2H), 7.24-7.

38 (m, 3 H) 7.47-7.58 (m, 1 H)

(Compound 41)

0.62-1.25 (m, 4 H) 1.67-1.84 (bs 1 H), 2.27 (s, 1 H), 3.45-4.2 (m, 7 H ), 6.70 6.96 (m,

2 H), 7.17 (d, 2 H), 27-40 (m, 3 H), 45-7.54 (m, 1 H)

(Compound 42)

0.70- 1.20 (m, 4 H), 1.67- 1.85 (b s, 1 H), 3

3 (s, 3H), 3.76 (s, 3H), 4.31 (s, 2H), 5.90

(t, 1 H), 6.84 (d, 2 H), 7.15 (d, 2 H),. 24-38 (m, 3 H), 7.50-7.60 (m, 1 H)

(Compound 43)

0.72-1.20 (m, 4H), 1.69-1.81 (m, 1H), 3.73 (s, 3H), 3.80 (s, 3H), 4. 30 (s, 2H), 4.85—5.12 (m, 1H), 6.79-6.90 (m, 2H), 7, 15 (d, 2 H), 7.25-7.38 (m, 3 H), 7.48-7.58 (m, 1 H) (Compound 44)

0.69-1.16 (m, 4H), 1.70-1.89 (bs, 1H), 2.49 (s, 3H), 3.73 (s, 3H), 3 78 (s, 3 H), 4.32

(s, 2H), 6.61 (d, 1H), 6.74 (s, 1H), 6.95 (d, 1H), 7.15-7.38 (m, 4 H), 7.49-7.60 (m, 1 H)

(Compound 45)

0.74-1.23 (m, 4H), 1.60—1.86 (bs, 1H), 3.73 (s, 3H), 3.78 (s, 3H), 4 . 33 (s, 2 H), 6.72-

6.88 (m, 1H), 7.02—7.14 (m, 2H), 7.26-7.38 (m, 3H), 7.48-7.58 (m, 1H H)

(Compound 46)

0.78-0.92 (m, 2H), 1.02-1.16 (m, 2H), 1.52-1.72 (bs, 1H), 3.72 (s, 3 H), 3.78 (s, 3H), 4.36 (s, 2H), 7.21-7.37 (m, 5H), 7.49 (d, 1H), 7.54 -7. 6 1 (m, 1 H)

(Compound 47)

0.72-1.18 (m, 4H), 1.68-1.86 (bs, 1H), 2.3

2 (s, 3H), 3.72 (s, 3H), 3.77 (s, 3H), 4.29 (s, 2H), 6.65 (d, 1H), 6.87 (s, 1 H), 7.10 0-7.

37 (m, 4H), 7.46-7.57 (m, 1 H)

(Compound 49)

0.77-1.20 (m, 4H), 1.59-2.02 (bs, 1H), 3.73 (s, 3H), 3.78 (s, 3H), 4 . 30 (s, 2 H), 6.98—

7.38 (m, 5 H), 7.47-7.58 (m, 2 H)

(Compound 50) 0.73-1.27 (m, 4H), 1.57-1.80 (bs, 1H), 2.28 (s, 1H), 3.48-4.72 (m, 7H ), 7.05—7.38 (m, 5 H), 7.42-7.60 (m, 2 H)

(Compound 51)

0.70- 1.15 (m, 4 H), 1.65- 1.79 (bs, 1 H), 3.73 (s, 3 H), 3.78 (s, 3 H), 4.31 (s, 2H), 6.96—7.04 (m, 1H), 7.28-7.38 (m, 4H), 7.41 -7.53

(m, 2 H)

(Compound 53)

0.74-1.18 (m, 4H), 1.58-1.78 (bs, 1H), 3.72 (s, 3H), 3.76 (s, 3H), 4 30 (s, 2 H), 6.88—

6.99 (m, 1 H), 7.11-7.21 (m, 1 H), 7.28-7.37 (m, 3 H), 7.41 (d, 1 H), 7 . 45-7.53 (m, 1 H)

(Compound 54)

0.72-1.25 (m, 4 H), 1.61-1.79 (bs, 1 H), 2.28 (s, 1 H), 3.54-3.88 (m, 3 8H), 4.19 (dd, 2H), 4.48-4.72 (m, 1.2H), 6.88—7.04 (m, 1H), 7.12-7 21 (m, 1 H), 7.28-7.37 (m, 3 H),

7.39-7.52 (m, 2H)

(Compound 55)

0.70-1.20 (m, 4H), 1.68-1.98 (bs, 1H), 3.75 (s, 3H), 3.78 (s, 3H), 4 31 (s, 2H), 6.89-7.06 (m, 2H), 7.11 (s, 1H), 7.22-7.39 (m, 3H), 7. 44-7.58 (m, 1 H)

(Compound 56)

0.68- 1.18 (m, 4H), 1.73—1.92 (bs, 1H), 2.3 0 (s, 6H), 3.74 (s, 3H), 3.77 (s, 3H), 4.31 (s, 2H), 6.48 (s, 2H), 6. 70 (s, 1 H), 7.25—7

40 (m, 3 H), 7.50- 7.60 (m, 1 H)

(Compound 57)

0.80-0.90 (m, 2H), 1.00-1.11 (m, 2H), 1.6-1-1.81 (bs, 1H) 3.73 (s, 3 H), 3.78 (s, 3 H), 4.28 (s, 2 H), 674 (s, 2 H), 7.04 (s, 1 H), 7.28-7.38 (m, 3 H) 7.46- 7.52 (m, 1 H)

(Compound 58)

0.70-0.90 (bs, 2H), 0.96-1-1.4 (bs, 2H), 1.78-1.92 (bs, 1H), 3.73 (s, 3H) , 3.77 (s, 6 H), 4.30 (s, 2 H), 6.01 (s, 2 H), 6.18 (s, 1 H), 7.24-7.35 ( m, 3 H), 7.5 1-7.59 (m, 1 H)

(Compound 59)

0.61-1.13 (m, 4H), 1.22 (t, 3H), 1.78-1.96 (bs, 1H), 3.63-3.85 (m, 9 H), 3.98 (q, 2H), 4.31 (s, 2H), 6.01 (s, 2H), 6.19 (s, 1H), 7.24- 7.38 (m, 3H), 7.49- 7.60 (m, 1H)

(Compound 62)

0.69- 1.16 (m, 4H), 1.78- 1.93 (bs, 1H), 3.44 (s, 3H), 3.66 (s, 3H), 3.78 (s, 6 H), 4.18

(dd, 2H), 4.65 (d, 1H), 5.10-5.33 (m, 1H), 6.02 (s, 2H), 6.18 (s, 1 H), 7.1 1 -7. 35 (m, 3 H), 7.45-7.54 (m, 1 H)

(Compound 63)

0.76-1.24 (m, 4H), 1.56-1.74 (bs, 1H), 3.7 5 (s, 3H), 3.79 (s, 3H), 4.33 (s, 2H), 6.63-7.01 (m, 2H), 7.20-7.40 (m, 3 H), 7.48-7.59

(m, 1 H)

(Compound 64)

0.82-1.15 (m, 4H), 1.51-1.70 (bs, 1H), 3.73 (s, 3H), 3.80 (s, 3H) , 4.38 (s, 2 H), 7.28—7.40 (m, 3 H), 7.50-7.60 (m, 1 H)

Example 3 (Adaptation of preparation)

(1) wettable powder

10 parts by weight of i-Daizo 58, 67.5 parts by weight of kaolin, 20 parts by weight of white carbon, 2 parts by weight of Neseki Rex Powder (trade name; manufactured by Kao Corporation), and Demol (trade name; And 0.5 parts by weight thereof were uniformly mixed and then ground to obtain a wettable powder.

(2) Dust

5 parts by weight of compound 58, 50 parts by weight of talc, and 45 parts by weight of kaolin were uniformly mixed to obtain a powder.

(3) Emulsion

Toxanone (trade name; manufactured by Sanyo Chemical Industries, Ltd.) (10 parts by weight) was added to 20 parts by weight of Yidani-Daizotsu 58 and 70 parts by weight of xylene, mixed uniformly, and dissolved to obtain an emulsion.

(4) Granules

5 parts by weight of Compound 58, 35 parts by weight of bentonite, 57 parts by weight of talc, 1 part by weight of Neobellex powder (trade name; manufactured by Kao Corporation), and 2 parts by weight of sodium lignin sulfonate are mixed uniformly, and then After adding and kneading a small amount of water, the mixture was granulated and dried to obtain granules.

Example 4 (Efficacy test)

(1) Control efficacy test for cucumber and disease (preventive effect) One cucumber (cultivar: Sagami Hanjiro) is grown per pot in a 6 cm diameter plastic flowerpot, and a 1.5-leaf seedling contains an acetone solution of the active ingredient compound and a surfactant. 0.05%) A drug diluted to a predetermined concentration with water was sprayed at 20 ml per pot.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then cucumber and zoospores were prepared from the diseased leaves, and the whole plant was inoculated by spraying on the reverse surface of the leaves.

After inoculation, the plants were kept in the dark for 2 days at 2 CTC for 1 day, and then grown in a glass greenhouse for 5 days. The control rate was calculated from the lesion area of the treated plot and the untreated plot.

In addition, as a comparative compound, the following formula described as compound N 0.57 in JP-A-5-177026:

And a compound A represented by the following formula described as compound No296 as described in JP-A-6-340607:

The compound B shown by was used. Control value is based on the percent control (%) are shown in Table 2, in 6 steps of 0 to 5 _£

Table 2

The results are shown in Table 3,

Table 3 Control value against cucumber and disease

(2) Control efficacy test for rice blast (preventive effect)

1 pot in a 6 cm diameter plastic flower pot 10 rice (cultivar: Nipponbare) The 2.5-leaf seedlings were diluted with a solution of the active ingredient compound in acetone containing a surfactant (0.05%) to a specified concentration in water, and lost in 20 ml per pot. did.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and the conidia suspension of rice blast fungus was uniformly inoculated into the leaves of the plants by spraying.

After inoculation, they were grown for 5 days in a humidity chamber at 25 ° C, and the degree of rice blast spots on the leaves was examined.

The drug effect was determined by comparing the degree of the lesion in the untreated section with the control value standard described in the above (1).

In addition, as a comparative compound, the compound A of the above (1) and the compound N 0.2 in JP-T-7-502747 were described.

The following formula:

CO ₂ CH

(C)

The compound c shown by was used.

The results are shown in Table 4.

Table 4 Control value against rice blast

(3) Efficacy test for the prevention of powdery mildew of ogi

A 10-year-old barley (cultivar: wheat) is grown in a plastic flowerpot with a diameter of 6 cm per pot, and an acetone solution of the active ingredient compound is surface-active on 1.5-leaf seedlings. A drug diluted to a predetermined concentration with water containing the agent (0.05%) was sprayed at 20 ml per pot.

After spraying, the plants were cultivated in a glass greenhouse for 2 days, and then the congeners of the congenium of the powdery mildew powdery mildew were collected from the diseased leaves and sprinkled evenly over the plants to inoculate them.

After the inoculation, they were raised in a glass greenhouse for 10 days, and the degree of the diseased wheat powdery mildew spots that appeared on the first leaf was investigated.

The drug effect was determined by comparing the degree of the lesion in the untreated plot with the control value standard described in the above (1).

As the comparative compounds, compound B of the above) and compound C of the above (2) were used. Table 5 shows the results. Table 5 Control value against oats powdery mildew

(4) Efficacy test for prevention of wheat rust (preventive effect)

Grow 10 wheat (cultivar: Kobushi wheat) per pot in a plastic flower pot with a diameter of 6 cm. A 1.5-leaf seedling contains an acetone solution of the active ingredient compound and a surfactant. (0.05%) A drug diluted to a predetermined degree with water was sprayed at 2 OmI per pot.

After spraying, the plants were cultivated for 2 days in a glass greenhouse, and then a suspension of spores of Fusarium head blight was uniformly inoculated by atomization. After inoculation, they were grown in a glass greenhouse for 10 days, and the degree of leaf rust spots of wheat on the first leaf was investigated.

The compound C of the above (2) was used as a comparative compound. Table 6 shows the results. Table 6 Control value against wheat rust

Industrial applicability

The N-phenyl carbamate compound of the present invention exhibits an excellent bactericidal action against rice blast fungus, cucumber fungus, barley powdery mildew, wheat rust, etc., and is useful as a fungicide for agriculture and horticulture. It is something.

Claims

The scope of the claims

1. The following equation (1)

In the formula, R ¹ is a hydrogen atom, an alkoxy group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, an alkenyl group or one C0 ₂ R ⁴ 3-5 carbon atoms; in here, R ⁴ represents 1-4 alkyl group having a carbon number; R ² represents an alkyl group having 1-4 carbon R ³ is a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, a cyano group, an alkoxy group having 1 to 4 carbon atoms, and 1 to 4 carbon atoms. An N-phenylcarbamate compound derivative represented by the following formula: wherein n represents an integer of up to 5; a haloalkoxy group, an alkylthio group having 1 to 4 carbon atoms, and a nitro group;

2. R 'is a hydrogen atom, selected from the group consisting of _{_{_{CH 3 0, C 2 H 5}}} 0, HC≡CCH 2, C 2 H 5, CH 3 0- CH 2, CH 2 = CHCH 2 and CH ₃ OCO 2. The N-phenyl carbamate compound derivative according to claim 1, which is a derivative thereof.

3.8 ² 1-1 ₃ or 0 ₂ 1-1 ₅ Dearu N- phenylene Rukaruba formate compound derivative ranging first claim of claim.

4. R ³ is hydrogen, halogen atom, methyl group, i-propyl group, trifluorome Selected from the group consisting of tyl, cyano, methoxy, ethoxy, trifluoromethoxy, tetrafluoroethoxy, hexafluoropropoxy, methylthio and nitro groups 2. The N-phenyl carbamate compound derivative according to claim 1, which is:

5. The compound is

(1) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ). Is a hydrogen atom;

(2) R ′ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _π is a halogen atom;

(3) R ¹ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkynyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a halogen atom;

(4) R ¹ is an alkoxyalkyl group having 2 to 5 carbon atoms, R ^∑ is an alkyl group having ⁴ to ⁴ carbon atoms, and (R ³ ) _η is a halogen atom;

(5) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is an alkyl group having 1 to 4 carbon atoms. Is;

(6) R ¹ is an alkoxy group having ¹ to ⁴ carbon atoms, R ² is an alkyl group having ¹ to ⁴ carbon atoms, and (R ³ ) _η is a haloalkyl group having 1 to 4 carbon atoms. some stuff;

(7) R ¹ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkyl group having 1 to ⁴ carbon atoms, and (R ³ ) _η is a haloalkyl group having 1 to 4 carbon atoms. some stuff;

(8) R ′ is an alkoxyalkyl group having 2 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) is an octaalkyl having 1 to 4 carbon atoms. What is the base.

(9) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _η is a cyano group;

(10) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _π is an alkoxy group having 1 to 4 carbon atoms. some stuff;

(11) R ¹ is a hydrogen atom, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _n is an alkoxy having 1 to 4 carbon atoms;

(12) R ′ is an alkenyl group having 3 to 5 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _n is an alkoxy group having 1 to 4 carbon atoms thing;

(13) R ¹ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkynyl group having 4 to 4 carbon atoms, and (R ³ ) _n is an alkoxy having 1 to 4 carbon atoms. ;

(14) R ¹ is an alkoxyalkyl group having 2 to 5 carbon atoms, R ² is an alkyl group having 4 to 4 carbon atoms, and (R ³ ) _n is an alkoxy group having 4 to 4 carbon atoms ;

(15) R 'is a gar C0 _² R ^4, R ₂ is 1 to 4 alkyl group having a carbon number,

(R ³ ) is an alkoxy having 1 to 4 carbon atoms;

(16) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _n is a haloalkoxy group having 1 to 4 carbon atoms. Is;

(17) R ′ is an alkynyl group having 3 to 5 carbon atoms, R ² is an alkyl group having ¹ to ⁴ carbon atoms, and (R ³ ) _n is a haloalkoxy group having 1 to 4 carbon atoms. Is;

(18) R ¹ is an alkoxy group having 1 to 4 carbon atoms, R ² is an alkyl group having 1 to 4 carbon atoms, and (R ³ ) _n is an alkylthio group; and

(19) R ¹ is an alkoxy group having 1 to ⁴ carbon atoms; R ² is an alkyl group having 1 to ⁴ carbon atoms; and (R ³ ) _n is a nitro group. The N-phenyl carbamate compound derivative according to claim 1, wherein

6. The compound is

Methyl N- [2- [cyclopropyl (4-methoxyphenylimino) methyl] thiomethylphenyl] dilubamate (compound 27),

Methyl N- [2- [cyclopropyl (4-methoxyphenylimino) methyl] thiomethylphenyl] 1-N-propargyl olebamate (compound 32), and methyl N- [2- [cyclopropyl (4 Xyphenylimi 2) The N-phenylcarbamate compound derivative according to claim 1, which is selected from the group consisting of (N) methyl] thiomethylphenyl] -N- (methoxy) caprate (compound 39). The following equation (2):

In the formula, R ² has the same meaning as described in claim 1; X is a chlorine atom or a bromine atom,

And a compound represented by the following formula (3):

In the formula, R ³ and n have the same meanings as described in claim 1.

Wherein the compound represented by the formula (1) is reacted with a compound represented by the following formula (1-a):

Wherein, R ^2, 8 ³ and 11 have the same meanings as defined above,

A method for producing an N-phenylcarbamate compound represented by the formula:

8. The reaction of the N-phenyl carbamate compound according to claim 7, wherein the reaction is carried out in the presence of a solvent and a base in a temperature range from 140 to the boiling point of the solvent to be used for 0.5 to 24 hours. Manufacturing method.

9. The following equation (1-a):

Wherein R ² , R ³ and n have the same meanings as described in claim 1, and a compound represented by the following formula (4):

R, one Y (4)

In the formula, R "is an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, an alkynyl group having 3 to 5 carbon atoms, an alkoxyalkyl group having 2 to 5 carbon atoms, or —C0 ₂ represents R ⁴ , wherein R ⁴ represents an alkyl group having 1 to ⁴ carbon atoms, Y represents a chlorine atom or an aodine atom,

Wherein the compound represented by the formula (1) is reacted with a compound represented by the following formula (1-b):

Wherein R, R ² , R ³ and n are as defined above,

A method for producing an N-phenyl carbamate compound represented by the formula:

10. The N-phenylcarbamate compound according to claim 9, wherein the reaction is carried out in the presence of a solvent, a base and a catalyst in a temperature range from 140 to the boiling point of the solvent to be used, from instantaneously to 12 hours. Recipe.

1 1. The following equation (5):

In the formula, R ¹ represents an alkoxy group having from 4 to 4 carbon atoms; R ² has the same meaning as described in claim 1, and X is a chlorine atom or a bromine atom; The following equation (3):

In the formula, >> ³ and 0 are the same as those in Claim 1.

Wherein the compound represented by the formula (1) is reacted with a compound represented by the formula (1-C):

In the formula, R ¹ has the same meaning as described above. R ² , ¾ ³ and 11 are as defined in claim 1,

12. The N-phenylcarbamate compound according to claim 11, wherein the reaction is carried out in the presence of a solvent and a radical in a temperature range from 140 to the boiling point of the solvent used for 0.5 to 24 hours. Recipe.

1 3. A fungicide for agricultural and horticultural use containing an N-phenylcarbamate compound represented by the formula (1) described in claim 1 as an active ingredient.