JPH046181B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] [Wherein, X is a lower fluoroalkyl group or a general formula

[Formula] Indicates a group represented by -OR ₃ or -CH ₂ R ₄ (where R ₂ is a lower alkenyl group,
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. Z is a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula

[In the formula, W and R ₇ have the same meanings as above. ]

A production method that involves reacting with the alcohol or thioalcohol shown in This reaction can be carried out without solvent or with benzene, toluene,
In an organic solvent such as xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, carbon tetrachloride, etc., without a catalyst or with triethylamine, N,N-diethylaniline, 1,4-diazabicyclo[2,
2,2]octane as a catalyst. The reaction is cooled or heated as necessary (0 to 50
°C), the process can be completed from instantaneous to 10 hours.
The target product can be obtained in good yield. The phenyl isocyanate derivative or phenyl isothiocyanate derivative represented by the above general formula [] is the general formula [] [In the formula, X, Y and R ₁ are as described above.] ] It can be obtained by reacting the aniline derivative represented by the following with phosgene or thiophosgene. This reaction is carried out in an organic solvent such as benzene, toluene, xylene, ethyl acetate or a mixture thereof. By heating from 50° C. to reflux temperature as necessary, the reaction can be completed instantly or in 10 hours, and the desired product can be obtained in good yield. Furthermore, the compound of the present invention can be produced, for example, by the following method. Method (c) General formula [] [In the formula, X, Y, R ₁ , A and B are as described above.] ] A compound represented by the general formula [] Z-R ₉ [] [wherein Z is as described above and R ₉ represents a leaving group. ] A manufacturing method of reacting with a compound represented by: In the above production method, examples of the leaving group include a halogen atom, a mesyloxy group, a tosyloxy group, and the like. This reaction involves benzene, toluene, xylene,
The desired product can be obtained in good yield by carrying out the reaction in an organic solvent such as dioxane chloroform or a mixture thereof, and using triethylamine, sodium hydroxide, sodium hydride, etc. The reaction was carried out at 0-150℃, and the reaction time was 12
Within hours. Next, a manufacturing example will be shown. Production example 1 Isopropyl N-(3-acetyloxy-4,
Synthesis of 5-diethoxyphenyl) carbamate (according to method (a)) 3-acetyloxy-4,5-diethoxyaniline (1.0 g) and N,N-diethylaniline (0.70 g) were dissolved in toluene (15 ml). and isopropyl chloroformate (0.70 g) was added dropwise under ice cooling for 5 minutes. After being left at room temperature for 12 hours, it was poured into ice water and extracted with ethyl acetate. Wash the extract layer with water,
Dry with magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography using a mixed solvent of benzene and tetrahydrofuran to obtain isopropyl N-(3-acetyloxy-4,
5-diethoxyphenyl) carbamate (1.21
g) was obtained (yield 88.9%). Physical constants mp108~109℃ NMRδ ^CDCl3 _TMS 1.25 (d, 6H), 1.30 (t, 3H),
1.38 (t, 3H), 2.27 (s, 3H), 3.96 (q, 2H),
4.00 (q, 2H), 4.95 (m, 1H), 6.46 (broad,
1H), 5.56 (d, 1H), 6.92 (d, 1H) Example 2 S-ethyl N-(3,4-diethoxy-5-
Synthesis of (difluoromethoxyphenyl) thiocarbamate (according to method (b)) 3,4-diethoxy-5-difluoromethoxyaniline (2.47 g) was dissolved in 20 ml of toluene and added to a toluene solution containing 10 g of phosgene at 10-20°C. dripped. After gradually heating and refluxing for 30 minutes, the mixture was returned to room temperature and the solvent was distilled off under reduced pressure to obtain 3,4-diethoxy-5-difluoromethoxyphenyl isocyanate. Without purification, add 1.0 g of triethylamine and 0.70 g of ethyl mercaptan.
was added dropwise to 50 ml of toluene solution containing At room temperature 12
After standing for an hour, it was poured into ice water and extracted with ethyl acetate. The extracted layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography using a mixed solvent of toluene and ethyl acetate to obtain S-ethyl N-(3,4-
diethoxy-5-difluoromethoxyphenyl)
Thiocarbamate (3.03g) was obtained (yield 90.5
%). Physical constant n ^25.0 _D 1.5291 Example 3 Synthesis of isopropyl N-methyl-N-(3,4-diethoxy-5-difluoromethoxyphenyl) carbamate (according to method (c)) Isopropyl N-(3,4-diethoxy -5
-difluoromethoxyphenyl) carbamate (3.33 g) and methyl iodide (4.30 g) were dissolved in tetrahydrofuran (10 ml). This solution was added dropwise to a tetrahydrofuran solution (20 ml) containing potassium hydroxide (1.68 g) and tetra-n-butylammonium bromide (1.0 g). After stirring at room temperature for 12 hours, the mixture was poured into ice water and extracted with toluene.
The extracted layer was washed with water, dried with magnesium sulfate,
It was distilled off under reduced pressure. The residue was purified by silica gel chromatography using a mixed solvent of toluene and ethyl acetate to obtain isopropyl N-methyl N-(3,4
-diethoxy-5-difluoromethoxyphenyl) carbamate (3.12 g) was obtained (yield 89.8
%). Physical constant n ^25.0 _D 1.4842 The compounds of the present invention thus obtained are illustrated in Table 1.

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[Table] When actually applying the compound of the present invention obtained in this way, it can be used in pure form without adding other ingredients, or it can be mixed with a carrier to make it easier to use as a fungicide. and commonly used forms such as powders, wettable powders, oils, emulsions,
It can be used as tablets, granules, microgranules, aerosols, flowables, etc. The above formulations generally contain 1.0 to 95.0% by weight of active compound (including mixed ingredients), preferably
Contains 2.0-80.0%, usually 10-100 per 10 ares
An application amount of 1.5 g is appropriate. Furthermore, the concentration used is
A range of 0.005 to 0.5% is desirable, but since the amount and concentration used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., there is no need to increase or decrease the amount without regard to the above range. No problem. Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides. Examples of formulations are shown below. Formulation Example 1 Powder 2 parts of the compound of the present invention (1), 88 parts of clay, and talc
By thoroughly grinding and mixing 10 parts, a powder with a base ingredient content of 2% can be obtained. Formulation Example 2 Wettable powder 30 parts of the compound of the present invention (3), 45 parts of diatomaceous earth, 20 parts of white carbon, 3 parts of wetting agent (sodium lauryl sulfate) and dispersing agent (calcium lignin sulfonate)
By thoroughly grinding and mixing the two parts, a hydrating agent with a base ingredient content of 30% can be obtained. Formulation Example 3 Wettable powder 50 parts of the compound of the present invention (17), 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
By thoroughly grinding and mixing 2.5 parts, a hydrating agent with a base ingredient content of 50% can be obtained. Formulation Example 4 Emulsion 10 parts of the compound of the present invention (14), 80 parts of cyclohexanone
If you mix 1 part and 10 parts of emulsifier (polyoxyethylene alkyl allyl ether), the main ingredient content will be 10%.
An emulsion is obtained. Next, test examples will be given to further clarify the usefulness of the compound of the present invention as an agricultural and horticultural fungicide. Note that the control compounds are indicated by the common names shown in Table 2.

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[Table] Note (1) Commercial herbicide Note (2) Commercial fungicide test example 1 Powdery mildew control effect on cucumber A 90 ml plastic pot was filled with sandy loam, and cucumber (variety: Sagami Hanshiro) was sown. This was cultivated at room temperature for 8 days to obtain cucumber seedlings with expanded cotyledons. A water-diluted solution of an emulsion of the compound of the present invention below and a hydrating powder of a control compound prepared according to Formulation Example 4 was sprayed on the seedlings until a sufficient amount of droplets adhered to the leaf surface. After the chemical solution was air-dried, the seedlings were spray inoculated with a conidial suspension of chemically resistant or sensitive cucumber powdery mildew fungus (Sphaerotheca fuliginea). The plants were cultivated at room temperature for 10 days to develop the disease, and then the disease state was observed. The disease severity was calculated by the following method. In other words, depending on the appearance of lesions on the investigated leaves, 0,
The disease was classified into indexes of 0.5, 1, 2, and 4, and the disease severity was calculated using the following formula. (Infection index) (Infection status) 0...No bacterial flora or lesions observed on the leaf surface. 0.5: Bacterial flora or lesions are observed on the leaf surface in less than 5% of the leaf area. 1...Bacterial flora or lesions are observed on the leaf surface in less than 20% of the leaf area. 2...Bacterial flora or lesions are observed on less than 50% of the leaf area. 4...Bacterial flora or lesions are observed on the leaf surface over 50% of the leaf area. Severity (%) = Σ {(Sickness index)
× (Number of leaves)}/(Number of investigated leaves) × 4 × 100 Subsequently, the control value was calculated using the following formula. Control value = 100 - (incidence in compound-treated area) / (incidence in non-treated area) x 100 As a result, as shown in Table 3, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria. However, when inoculated with drug-susceptible bacteria, no control effect was shown. On the other hand, none of the commercially available fungicides, benomyl, thiophanate methyl, and carbendazim, showed any control effect when inoculated with drug-resistant bacteria, but showed excellent control effects when inoculated with drug-susceptible bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.

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[Table] Test example 2 Sugar beet brown spot control effect Fill a 90ml plastic pot with sandy loam and add sugar beet (variety: Detroit dark red)
was sown. The seedlings obtained after 20 days of cultivation in a greenhouse were coated with a water-diluted solution of an emulsion of the compound of the present invention below and a hydrating powder of a control compound prepared according to Formulation Example 4 until the droplets sufficiently adhered to the leaf surface. Spread.
After the chemical solution was air-dried, the seedlings were spray inoculated with a conidial suspension of chemically resistant or susceptible Cercospora beticola. After cultivating the plants in a greenhouse for 10 days under humid conditions by covering them with a vinyl cover, the state of disease development was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As shown in Table 4, similar to the results of Test Example 1, the compound of the present invention exhibited an excellent control effect when inoculated with drug-resistant bacteria; Jim showed excellent control effects when inoculated with drug-susceptible bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.

[Table] Test Example 3 Pear scab control effect A 90 ml plastic pot was filled with a mixed soil of peat moss and sandy loam, and seeds collected from pear fruit (variety: Chojuro) were sown. 20 minutes at room temperature
An emulsion of the present compound described below prepared according to Formulation Example 4 and a water-diluted solution of a hydrating powder of the control compound described below were sprayed on the foliage of the seedlings grown for one day until the droplets sufficiently adhered to the leaf surface. After the leaf liquid was air-dried, the seedlings were spray-inoculated with a conidial suspension of drug-resistant or susceptible Venturia nashicola. 3 under humid conditions at 20°C.
The plants were then cultivated for 20 days under fluorescent lighting at 20°C to develop the disease. The disease onset investigation method and control value calculation were the same as in Test Example 1. As a result, as shown in Table 5, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. It was shown to be effective.

[Table] Test Example 4 Peanut brown spot control effect A 100 ml plastic pot was filled with sandy loam and peanuts (variety: Chiba semi-erect) were sown. The seedlings obtained after 14 days of cultivation in a greenhouse,
10 ml of a water-diluted solution of an emulsion of the compound of the present invention below and a hydrating powder of the control compound below prepared according to Formulation Example 4 was sprayed on foliage per pot. After the chemical solution was air-dried, the seedlings were spray-inoculated with a spore suspension of chemically resistant or susceptible peanut brown spot fungus (Cercospora arachidicola). After cultivating it in a greenhouse for 10 days under humid conditions by covering it with a vinyl cover, the state of disease development was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As a result, as shown in Table 6, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. It was shown to be effective.

[Table] Test Example 5 Control effect on gray mold disease of cucumber A 90 ml plastic pot was filled with sandy loam, and cucumber (variety: Sagami Hanshiro) was sown. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. To these seedlings, 10 ml per pot of a water diluted solution of an emulsion of the compound of the present invention below and a hydrating powder of the control compound below, prepared according to Formulation Example 4, was sprayed on the foliage. After the chemical solution was air-dried, the young seedlings were inoculated with bacterial colony cuttings (5 mm in diameter) of chemically resistant or sensitive Botrytis cinerea by pasting them on the leaves. This was left under humid conditions at 20°C for 3 days to develop the disease, and then the state of disease onset was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As a result, as shown in Table 7, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. It was shown to be effective.

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[Table] Test Example 6 Effect on controlling cucumber vine blight A 90 ml plastic pot was filled with sandy loam, and cucumbers (variety: Sagami Hanshiro) were sown. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. To these seedlings, 10 ml per pot of a water diluted solution of an emulsion of the compound of the present invention below and a hydrating powder of the control compound below, prepared according to Formulation Example 4, was sprayed on the foliage. Chemical resistant or susceptible cucumber vine blight fungus (Mycosphaerella melonis) on young seedlings after air-drying the chemical solution.
A cut plate (5 mm in diameter) of the bacterial flora was pasted on the leaf surface and inoculated. This was left under humid conditions at 20°C for 3 days to develop the disease, and then the state of disease onset was observed. The disease onset investigation method and control value calculation were performed in the same manner as in Test Example 1. As a result, as shown in Table 8, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. It was shown to be effective.

[Table] Test Example 7 Effect on controlling citrus blue mold disease After thoroughly washing citrus fruit (variety: Unshu) with water and air drying, dilute the emulsion of the compound of the present invention below prepared according to Formulation Example 4 and the control commercially available drug below with water. The sample was immersed in a chemical solution with a predetermined concentration for 1 minute. After air drying, drug-resistant or sensitive conidia of Penicillium italicum were suspended in water and sprayed to inoculate the fruit surface. After being kept in a moist room for 14 days after inoculation, the degree of disease onset was investigated using the disease index of 0, 1, 2, 3, 4, and 5 as shown below. (Disease condition) (Incidence index) No lesions observed 0 Lesions observed on less than 20% of the fruit surface area 1 Lesions observed on less than 20-40% 2 40-60% 3 60 ~80% 〃 4 〃 Lesions are observed in 80% or more 5 The disease severity and control value were calculated in the same manner as in Test Example 1. As a result, as shown in Table 9, the compounds of the present invention showed excellent control effects when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiophanate methyl showed excellent control effects when inoculated with drug-susceptible bacteria. It was shown to be effective.

[Table] Test Example 8 Test for phytotoxicity on crops Fill 150ml plastic pots with sandy loam and add wheat (variety: Norin No. 61) and apples (variety: Norin No. 61).
Kogyoku) and peanuts (variety: Chiba semi-erect) were sown and cultivated in a greenhouse. The obtained seedlings were sprayed with a water diluted emulsion of the compound of the present invention described below and a hydrating powder of the control compound described below, which were prepared according to Formulation Example 4. After spraying, the plants were placed in the greenhouse again, and after cultivation for 10 days, the presence or absence of phytotoxicity was investigated according to the following criteria. Standards for degree of drug damage (degree) (symptoms) - No abnormalities. + Abnormalities caused by chemical damage are observed in some of the crops. Abnormalities due to chemical damage are observed throughout the crop. The plant dies due to chemical damage. As a result, as is clear from Table 10, the compound of the present invention had no harmful effect on crops, and the commercially available herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.

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Claims (1)

[Claims] 1. General formula [] _{[ wherein , _}
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. Z represents a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a group represented by the general formula [Formula] or -S-R ₆ (where R ₅ is a lower represents an alkyl group, a lower cycloalkyl group, or a phenyl group, R ₆ is a lower alkyl group,
Indicates a lower alkoxycarbonyl group or phenyl group. ). R ₁ represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cyano group, or a lower substituted with any group or atom among a halogen atom, a lower alkoxy group, a cyano group, and a lower cycloalkylalkyl group. Indicates an alkyl group. A represents an oxygen atom or a sulfur atom. B is a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or the general formula -
Indicates a substituent represented by WR ₇ (where W represents an oxygen atom or a sulfur atom, R ₇ is a lower cycloalkyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group,
represents a lower haloalkynyl group or a lower cycloalkylalkyl group, or at least one of a halogen atom, a cyano group, a lower alkoxy group, a phenyl group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group Indicates a lower alkyl group substituted with a group or an atom. ] Aniline derivative represented by. 2 In the above general formula [], X is a fluoromethyl group, difluoromethyl group, trifluoromethyl group, methylthiocarbonyl group, allyloxy group, propargyloxy group, methoxymethoxy group, methylthiomethoxy group, difluoromethoxy group, or 2-chloroethoxy group, Y is a methyl group, methoxy group, ethoxy group, chlorine atom, bromine atom or methoxymethyl group, Z is a hydrogen atom, A is an oxygen atom, and B has 1 to 1 carbon atoms.
5 alkoxy group, alkenyloxy group having 2 to 5 carbon atoms, alkynyloxy group having 2 to 5 carbon atoms, haloalkoxy group having 1 to 5 carbon atoms, haloalkenyloxy group having 2 to 5 carbon atoms, and haloalkenyloxy group having 2 to 5 carbon atoms. The aniline derivative according to claim 1, which is a haloalkynyloxy group having 5 carbon atoms or a cyanoalkoxy group having 1 to 5 carbon atoms. 3 General formula _{[ wherein , _}
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. Z represents a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a group represented by the general formula [Formula] or -S-R ₆ (where R ₅ is It represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group, and R ₆ represents a lower alkyl group, a lower alkoxycarbonyl group, or a phenyl group.) R ₁ represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cyano group, or a lower substituted with any group or atom among a halogen atom, a lower alkoxy group, a cyano group, and a lower cycloalkylalkyl group. Indicates an alkyl group. ] Compound and general formula shown by [In the formula, A represents an oxygen atom or a sulfur atom. B represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or a substituent represented by the general formula -WR ₇ (here, W represents an oxygen atom or a sulfur atom, and R ₇ represents a lower cycloalkyl group) basis,
A lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkylalkyl group, or a halogen atom, a cyano group, a lower alkoxy group, a phenyl group, a lower alkenyloxy group, Indicates a lower alkyl group substituted with at least one group or atom among a lower haloalkoxy group, a phenoxy group, and a lower aralkyloxy group. ). _R8
indicates a halogen atom. ] Compound or general formula represented by [In the formula, A is as described above.] B' represents a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group or a phenyl group. ] A general formula characterized by reacting with a compound represented by [In the formula, X, Y, Z, R ₁ , A and B are as described above. ] A method for producing the compound shown in 4 General formula _{[ wherein , _}
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. R ₁ represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cyano group, or a lower substituted with any group or atom among a halogen atom, a lower alkoxy group, a cyano group, and a lower cycloalkylalkyl group. Indicates an alkyl group. A represents an oxygen atom or a sulfur atom. ] A compound represented by the general formula H-W-R ₇ [wherein, W represents an oxygen atom or a sulfur atom]. R ₇
represents a lower cycloalkyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkylalkyl group, or a halogen atom, a cyano group, a lower alkoxy group, or a phenyl group. ,
Indicates a lower alkyl group substituted with at least one group or atom among a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, and a lower aralkyloxy group. ] A general formula characterized by reacting with a compound represented by [In the formula, X, Y, R ₁ , A, W and R ₇ are as described above. ] A method for producing an aniline derivative represented by 5 General formula _{[ wherein , _}
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. R ₁ represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cyano group, or a lower substituted with any group or atom among a halogen atom, a lower alkoxy group, a cyano group, and a lower cycloalkylalkyl group. Indicates an alkyl group. A represents an oxygen atom or a sulfur atom. B is a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or the general formula -
Indicates a substituent represented by WR ₇ (where W represents an oxygen atom or a sulfur atom, R ₇ is a lower cycloalkyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl lower haloalkenyl group, a lower haloalkynyl group) or a lower cycloalkylalkyl group, or a halogen atom, a cyano group, a lower alkoxy group, a phenyl group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group,
It represents a lower alkyl group substituted with at least one group or atom among lower aralkyloxy groups. ] Compounds represented by the general formula Z-R ₉ [wherein Z is a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or the general formula [formula] or -S -R ₆ represents a group (here, R ₅ represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group, and R ₆ represents a lower alkyl group, a lower alkoxycarbonyl group, or a phenyl group). R ₉ represents a leaving group. ] A general formula characterized by reacting with a compound represented by [In the formula, X, Y, Z, R ₁ , A and B are as described above. ] A method for producing an anilile derivative represented by. 6 General formula _{[ wherein , _}
Represents a lower alkynyl group, cyano group or lower alkylthio group, R ₃ is a lower alkylcarbamoyl group,
It represents a lower alkenyl group, a lower alkynyl group, a cyano group, an acyl group, a lower alkoxycarbonyl group, or a hydrogen atom, or is substituted with any group or atom among a lower alkoxy group, a lower alkylthio group, a cyano group, or a halogen atom. R ₄ represents an acyl group, a lower alkylthio group, a lower alkylcarbamoyloxy group or an acyloxy group. ). Y represents a lower alkyl group, a lower alkoxy group, a halogen atom or a lower alkoxymethyl group. Z represents a hydrogen atom, a hydroxyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a group represented by the general formula [Formula] or -S-R ₆ (where R ₅ is a lower represents an alkyl group, a lower cycloalkyl group, or a phenyl group, R ₆ is a lower alkyl group,
Indicates a lower alkoxycarbonyl group or phenyl group. ). R ₁ represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a cyano group, or a lower substituted with any group or atom among a halogen atom, a lower alkoxy group, a cyano group, and a lower cycloalkylalkyl group. Indicates an alkyl group. A represents an oxygen atom or a sulfur atom. B is a lower alkyl group, a lower alkenyl group, a lower cycloalkyl group, a phenyl group, or the general formula -
Indicates a substituent represented by WR ₇ (where W represents an oxygen atom or a sulfur atom, R ₇ is a lower cycloalkyl group, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group,
represents a lower haloalkynyl group or a lower cycloalkylalkyl group, or at least one of a halogen atom, a cyano group, a lower alkoxy group, a phenyl group, a lower alkenyloxy group, a lower haloalkoxy group, a phenoxy group, a lower aralkyloxy group Indicates a lower alkyl group substituted with a group or an atom. ] An agricultural and horticultural fungicide characterized by containing an aniline derivative represented by the following as an active ingredient.