JPS61171462A - Aniline derivative, preparation thereof, and agricultural and horticultural fungicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (X and Y are lower alkylene or lower alkoxy-lower alkylene; k, l, m and n are 0 or 1; R1 is nitro, 2- nitrovinyl, etc.; Z is H, OH, lower alkyl, etc.; A is O or S; B is lower alkyl, lower alkenyl, etc.). USE:Fungicide for agricultural and horticultural use. It has excellent controlling effect against drug-resistant fungi. PREPARATION:The compound of formula I can be produced by reacting the compound of formula II with the compound of formula III (R6 is halogen) in a solvent (e.g. water, benzene, toluene, etc.) at 0-150 deg.C, optionally in the presence of a base (e.g. pyridine, triethylamine, etc.).

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel aniline derivative, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient.

Since systemic fungicides have been used for crop disease control, the problem of drug-resistant bacteria has become increasingly important. In fields where drug-resistant bacteria are prevalent, it is no longer possible to expect the drugs to have sufficient efficacy. Examples of such drugs include benomyl [methyl 1-(butylcarbamoyl)benzimidazole-2-ylbamate], fuberidazole [2-(2-furyl)benzimidazole], and thiabendazole [2-thiazol-4-ylbenzimidazole]. dazole], carpendazim [methyl benzimidazole-2-ylbamate], thiophanate methyl [
dimethyl 4.4-o-)unisine bis(8-thioallophanate)], thiophanate [dimethyl 4.4
-o-phenylene bis(8-thioallophanate)]
benzimidazole/thiophanate fungicides such as, procyton (N-(8',5'-dichlorophenyl)-1゜2-dimethylcyclopropane-1,2-dicarboximide), iprodione (8-(8 ', 5'
-dichlorophenyl)-N-isopropyl-2゜4-dioxoimidazolidine-1-carboxamide], vinclozolin (8-1',5'-dichlorophenyl)-
5-methyl-5-1'yl-1,8-oxazolidine-
2,4-dione], dicrosilinate [ethyl 8-(
8',5'-dichlorophenyl)-5-methyl-2,4
-dioxoxazolidine-5-carboxylate] and the like.

In view of this situation, the present inventors conducted various studies in order to develop a compound that is effective against the aforementioned drug-resistant bacteria. Represents an alkylene group or a lower alkoxy lower alkylene group.

kp l s m and n are the same or different and represent 0 or l.

R1 is a nitro group, a 2-nitrovinyl group, an amino group, an isothiocyanato group, a lower alkylamino group, or a ru(0)p group represented by the general formula % -5O, -NH-R, or -5-R. (Here, A' and A'' are the same or different and represent an oxygen atom or a sulfur atom, and R2 and R
; are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0.1 or 2. ).

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 -C-R3 or -SR4 (where R3 is a lower alkyl group, (represents a lower cycloalkyl group or phenyl group, and R4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group).

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 (where W represents an oxygen atom or a sulfur atom, and R11 represents a lower alkyl group). group, lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or a halogen atom, a cyano group , phenyl group, lower cycloalkyl group, or lower alkoxyl group, and represents an alkyl group substituted with at least one atom or group). ] was discovered, leading to the present invention.

Examples of drug-resistant bacteria for which the compound of the present invention represented by general formula (1) exhibits a strong bactericidal effect include Podosphaera 1eoucotrich.
a), Venturia 1naequal
is), Venturia nas
hicola), Scler-otin
ia mali), oyster anthracnose fungus (G loeosp
oriumkaki), peach gray layer fungus (5cler
otinia cinerea), Cla
dosprium carpophilum), Botrytis cinerga
), E 1sinoe ampel
1na), late rot fungus (Glomerella
lata), sugar beet brown spot fungus (Cercospor
abeticola), peanut brown spot fungus (Ce
rcospora arachidicola), Cercospora personata,
Erysiphe gram
inis f.

sp, hordei), eye spot fungus (Cer.
cosporellaherpotichoides)
, Fusarium nivale
, wheat powdery mildew (E rys i phegr)
aminis f, Spa tritici),
Powdery mildew of cucumber (S phaerotheca)
ful 1g1nea), vine blight fungus (Mycos
phaerel la melonis), Botrytis cinerea, Cladosporiumeca humuli
, Botryt-is cin
area), tobacco powdery mildew (Erysip-
he cichoracearum), rose scab @ (D 1ploca-rpon rosae),
Elsinoefawcetii
), Penicillium itali
c-um), Penicillium d
gitatum), etc.

Next, the method for producing the compound of the present invention represented by general formula [1] will be explained in detail.

Production method (a): The compound of the present invention has the general formula CI) [wherein X, Y, l, m, n, R1 and Z have the same meanings as above. ] A compound represented by the general formula % formula % [wherein A and B represent the same meanings as above, and R6
represents a halogen atom. ] in a solvent, if necessary in the presence of a base, usually at θ to 150"C. Examples of solvents include water, benzene, toluene, xylene, etc. ,
diethyl ether, tetrahydrofuran, dioxane,
Chloroform, carbon tetrachloride, ethyl acetate, pyridine, N
, N-dimethylformamide, etc., and examples of the base include pyridine, triethylamine, NlN-diethylaniline, sodium hydride, potassium hydroxide, and the like. A phase transfer catalyst, such as tetra-n-butylammonium bromide, can also be used if desired.

When the substituent 2 represents a hydrogen atom in the general formula (1), the compound of the present invention is a compound of the general formula (1) [wherein X, Y,
1, m, n, R1 and A have the same meanings as above. ] A phenyl isocyanate derivative represented by the general formula % [wherein RII and W represent the same meanings as above].

] The compound represented by is added without a solvent or in a solvent, usually at θ
It can be produced by reacting at ~50°C. Examples of solvents include benzene, toluene,
Examples include xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, and carbon tetrachloride. If necessary, a base such as triethylamine 1,N,N-diethylaniline or 1,4-diazabicycloC2,2,2)octane can be used as a catalyst. The reaction is usually completed within 10 hours.

In addition, the phenyl isocyanate derivative represented by the general formula [summer] is prepared by combining the corresponding aniline derivative and phosgene or thiophosgene in an organic solvent such as benzene, toluene,
It can be obtained by reacting in xylene, ethyl acetate) at a temperature usually from 50°C to reflux.

The reaction is usually completed within 10 hours.

In the production method (C) (general formula CI), when the substituent 2 is not a hydrogen atom, the compound of the present invention can be prepared by the general formula (ff) [wherein, X # Y
e k * l # " m " t Rt # A and B represent the same meanings as above. ] An aniline derivative represented by the general formula (V) Z'-R,
(Ma) [In the formula, 2' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula, where R3 represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group. ), and R4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group. ), R7 represents a leaving group. ] The compound represented by
It can be produced by reacting at ~100°C. The reaction is usually completed within 12 hours. The leaving group here represents a halogen atom, mesyloxy group or tosyloxy group. Examples of the solvent include N.

Examples of the base include N-dimethylformamide, dimethyl sulfoxide, diethyl ether, and tetrahydrofuran. Examples of the base include sodium hydride and potassium hydroxide.

Production (d): When the groups represented by are the same and represented by the general formula [wherein A', A'' and R1 have the same meanings as above], the compound of the present invention is General formula (V
l) NH! [In the formula, x ey * ke l# m and n represent the same meanings as above. ] Compounds represented by the general formula [■] R, -R, (■) [In the formula, R8 represents a halogen atom, and R represents a substituent (herein, A', A'' and R2 are It can be obtained by reacting the compound represented by the formula (having the same meaning as above) in the same manner as in the production method (a).

The compound represented by the general formula (Vl) has the general formula CVt
+ [In the formula, x, Y, l2m and n represent the same meanings as above. ] It can be produced by reducing the compound shown in the following.

The reaction is carried out in a solvent (e.g., ethanol, ethyl acetate, dioxane) and a catalyst (e.g., platinum dioxide, palladium on carbon) under a hydrogen atmosphere of usually 1 to 100 atm.
It is carried out at 0-200°C. This reaction is usually completed within 12 hours.

In addition, compound (9) is described in Document J, Chem, Soc
,.

It can be synthesized by the method described in 1981.2492.

Next, production examples of the compounds of the present invention will be shown.

Production example 6.8-diamino-1,8-benzodioxane 8.82
Methyl chloroformate 8.18f in a mixture of f,N,N-diethylaniline 6.0Of and dioxane 6011/
was added dropwise over 6 minutes under water cooling. The reaction solution was heated to 1 at room temperature.
After standing for 2 hours, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.

The obtained residue was purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate to obtain 6,8-bis(methoxyallcarbonylamino)-1,
8-Benzodioxane [Compound number (44)) 4.94
I got an F.

Yield: 87.6% m @ p * 156.5-157.5°C In the same manner, 16-itupropoxycarbonylamino-8-methoxycarbonylamino-1,8-benzodioxane [Combination control ft
42>) m, p, 159-160.5°C
and 6-nitoxycarbonylamino-8-methoxycarbonylamino-1,8-benzodioxane [compound number (4g)) m, p, 149-150°C were obtained.

The compounds of the present invention thus obtained are illustrated in Table 1.

When the compound of the present invention is used as an active ingredient of an agricultural and horticultural fungicide, it may be used as is without adding any other ingredients;
Usually, it is mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries to formulate an emulsion, a wettable powder, a suspension, a powder, a liquid, and the like.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 95%, preferably 2 to 80%.

As solid carriers, fine powders such as kaolin clay, attapulgite clay, bentonite, acid clay, pyroferrite, talc, diatomaceous earth, calcite, 'corn cob powder, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silicon oxide, etc. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, soybean oil, and cottonseed oil. Examples include vegetable oils such as, dimethyl sulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate salts, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, l-lyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block coho 0
Examples include nonionic surfactants such as reamer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester.

As formulation adjuvants, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC
(carboxymethylcellulose), PAP (isopropyl acid phosphate), and the like.

Examples of formulations are shown below.

Formulation Example 1 Powder 2 parts of the compound of the present invention (44), 88 parts of clay, and 10 parts of talc are thoroughly ground and mixed to obtain a powder containing 2% of the main ingredient.

Formulation Example 2 Wettable powder 80 parts of the compound of the present invention (44), 45 parts of diatomaceous earth, 20 parts of white carbon, 8 parts of a wetting agent (sodium lauryl sulfate) and 2 parts of a dispersing agent (calcium lignin sulfonate) were thoroughly ground and mixed. A hydrating agent with a base ingredient content of 80% is obtained.

Formulation Example 8 Wettable powder 50 parts of the compound of the present invention (44), ±45 parts of diatom, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and 2.6 parts of dispersing agent (calcium ligninsulfonate) were thoroughly ground and mixed. A hydrating agent having a base agent content of 50% is obtained.

Formulation Example 4 Emulsion Compound of the present invention (44) 10 parts, cyclohexanone 80 parts
1 part and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) to obtain an emulsion with a base agent content of 10%.

The application rate of the preparation obtained as described above is usually 10 to 10 (l) per 10 are.

Further, the concentration used is preferably in the range of 0.005 to 0.5%, but the amount and concentration used vary depending on the dosage form, application time, method, location, target disease, target crop, etc., so it is not limited to the above range. There is no problem with increasing or decreasing the amount regardless of B.

Furthermore, it can be used in combination with other fungicides, herbicides, plant growth regulators and insecticides.

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.

Table 2 Note (1) Commercial herbicide Note (Takumi Commercial fungicide test example 1 Cucumber powdery mildew control effect Fill a 90 liter plastic pot with sandy loam and sow cucumbers (variety: Sumo Hanshiro) This was cultivated at room temperature for 8 days to obtain cucumber seedlings with expanded cotyledons.These seedlings were treated with an aqueous dilution of the following emulsion of the present compound and a hydrating powder of a control compound prepared wI4 according to Formulation Example 4. was sprayed on the foliage until enough droplets adhered to the leaf surface.

Chemical resistant or sensitive cucumber powdery mildew on young seedlings after air-drying the chemical solution! i (Sphaerotheca fuli)
gi-nea) was inoculated by spraying with a conidial suspension. After cultivating this in a greenhouse for 10 days to develop disease, the disease state was observed.

The disease severity was calculated by the following method.

That is, depending on the appearance of lesions on the investigated leaves, on 010.5.1
．． The disease was classified into an index of 2.4, and the disease severity was calculated using the following formula.

(Incidence index) (Infection state) O: No WIWl 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 the leaf surface in less than 50% of the leaf area.

4...Bacterial flora or lesions are observed on the leaf surface over 50% or more of the leaf area.

Next, the control value was calculated using the following formula.

As a result, as shown in Table 8, the compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria. On the other hand, the commercially available fungicides benomyl, thiophanate methyl, and carpendazim all showed excellent control effects when inoculated with drug-resistant bacteria, and 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 8 Test Example 2 Effect on controlling sugar beet brown spot disease A 90 g/volume plastic pot was filled with sandy loam, and sugar beet (variety: Detroit Dark Red) was sown.

Formulation Example 4 was applied to seedlings obtained after 20 days of cultivation in a greenhouse.
An emulsion of the compound of the present invention described below and a water-diluted solution of a hydrating powder of a control compound prepared according to the method described below were sprayed on foliage until the droplets sufficiently adhered to the leaf surface. After air-drying the chemical solution, the seedlings were exposed to chemically resistant or susceptible sugar beet brown spot (Cercospora bet).
icola) was inoculated by spraying with a conidial suspension. Cover this with a vinyl cover to create a humid condition, and place it in a greenhouse at 1000 ml.
After cultivation for one day, the disease state 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 compounds of the present invention exhibited excellent control effects when inoculated with drug-resistant bacteria, whereas the commercially available fungicides benomyl, thiophanate methyl, and carpendazim showed drug-resistant bacteria. It showed excellent control effect when inoculated with bacteria. Commercially available herbicides with similar chemical structures showed almost no control effect when inoculated with any of the bacteria.

Table 4 Test Example 8 Pear scab control effect 90g/volume A plastic pot was filled with a mixed soil of peat moss and sandy loam, and seeds collected from pear fruit (variety: Chojube) were sown.

This was cultivated in a greenhouse for 20 days, and a water diluted solution of an emulsion of the compound of the present invention prepared according to Formulation Example 4 below and a hydrating powder of the control compound below was applied to the resulting seedlings until the droplets sufficiently adhered to the leaf surface. Sprayed on foliage. After air-drying the chemical solution, young seedlings were infected with drug-resistant or susceptible pear scab fungus (Venturia rrasbi).
cola) was inoculated by spraying with a conidial suspension. The plants were placed under humid conditions at 20°C for 8 days, and then cultivated under fluorescent lighting at 20°C for 20 days 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 an excellent control effect 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. Indicated.

Table 6 Test Example 4 Peanut brown spot control effect A 100gl plastic pot was filled with sandy loam, and peanuts (variety: Nichiba semi-erect) were sown. After 14 days of cultivation in a greenhouse, the resulting seedlings were sprayed with 10xl per pot of a water diluted emulsion of the compound of the present invention prepared according to Formulation Example 4 and a hydrating powder of the control compound below. After the chemical solution is air-dried, the seedlings are infected with chemical-resistant or susceptible peanut brown spot fungus (Cercospora arachidicola).
) was inoculated by spraying with a spore suspension. After cultivating it in a greenhouse for 10 days under humid conditions by covering it with a vinyl cover,
The disease state was observed. The disease onset investigation method and control value calculation were carried out in the same manner as Test Example 1.

As a result, as shown in Table 6, the compounds of the present invention exhibited 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. Indicated.

Table 6 Test Example 6 Cucumber gray mold control effect A 90 m capacity plastic pot was filled with sandy loam, and m types of cucumbers (variety: Sumo Hanshiro) were planted. This was cultivated in a greenhouse for 8 days to obtain cucumbers with expanded cotyledons. To these seedlings, an emulsion of the compound of the present invention prepared according to Formulation Example 4 and a water diluted solution of a hydrating powder of the control compound below were added to the seedlings at 10 g/pot! Sprayed with stem vegetables. After air-drying the chemical solution, the cucumber gray mold fungus (Botrytis cinere
For inoculation by gluing the Wi cut version (diameter 511 m) of a) onto the leaf surface. This was weighed under humid conditions at 20° C. for 8 days to induce 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 exhibited excellent control effects when inoculated with drug-resistant bacteria, and the commercially available inverse Eζ pesticides, benomyl and thiophanate methyl, showed excellent control effects when inoculated with drug-susceptible bacteria. Indicated.

Table 7 Test Example 6 Effect on controlling cucumber vine blight A plastic pot with a capacity of 90 sZ was filled with sandy loam, and cucumbers (variety: Sumo Half-day) were sown. 8 in a greenhouse
After cultivation for several days, cucumbers with expanded cotyledons were obtained. To these young seedlings, an emulsion of the following present compound prepared according to Formulation Example 4 and a water diluted solution of a hydrating powder of the following control compound were sprayed on the foliage at a rate of 10 TId per pot. After air-drying the chemical solution, seedlings are infected with drug-resistant or sensitive cucumber vine blight fungus (Myc).
osphaerella melonis) cD bacterial lawn cuttings (diameter 5 fl.) were pasted onto the leaf surface and inoculated.

After weighing this for 8 days under humid conditions at 20 degrees Celsius to induce disease,
The disease state 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 compound of the present invention showed an excellent control effect 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. Ta.

Table 8 Test Example 7 T-kan blue mold control effect After thoroughly washing tangerine fruit (variety: Unshu) with water and air drying,
The following emulsion of the present compound prepared according to Formulation Example 4 and the following control commercially available drug were diluted with water and immersed in a drug solution of a predetermined concentration for 1 minute. After air-drying, a drug-resistant or susceptible tangerine blue mold fungus (Penicillium italic)
um) Conidia were suspended in water and sprayed onto the fruit surface.

After inoculation, the seeds were kept in a humid room for 14 days, and then the severity of disease was investigated using the disease onset index of ζ0.1.2.8.4.6 as shown below. (Infection status) (Infection index) No lesions observed 0 20% of fruit surface area
Lesions are observed in less than #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 compound of the present invention showed an excellent control effect when inoculated with drug-resistant bacteria, and conversely, the commercially available fungicides benomyl and thiono-1 nate-methyl showed excellent control effects when inoculated with drug-susceptible bacteria. showed that.

Table 9 Test Example 8 Phytotoxicity test on crops A 150 g/volume plastic pot was filled with sandy loam,
Wheat (variety: Norin No. 61), apple (variety: Kogyoku),
Beach 1 F 1 item moderate: Chiba semi-erect) each L type,
Grown 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 Grade C) (Symptoms) - No abnormalities.

10. Abnormalities due to chemical damage are observed in some of the crops.

Abnormalities due to chemical damage are observed throughout the crop.

+Dying occurs due to chemical damage.

As a result, as is clear from Table 10, the compound of the present invention did not have a phytotoxic effect on crops, whereas a commercially available herbicide with a chemical structure similar to that used as a control had a phytotoxic effect.

1゜

Claims (6)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
2-A'-R_2, -SO_2-NH-R_2 or -S-R_2 (where A' and A'' are the same or different and represent an oxygen atom or a sulfur atom, and R_2 and R '_2 are the same or different, lower alkyl group,
Represents a lower alkenyl group, lower alkynyl group, lower haloalkyl group or lower alkoxyalkyl group, p is 0
, 1 or 2. ). 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 ▲ Numerical formula, chemical formula, table, etc. ▼ or -SR_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group or phenyl group, and R_4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl 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 -W-
Represents a substituent represented by R_5 (where W represents an oxygen atom or a sulfur atom, R_5 is a lower alkyl group,
Represents a lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, a cyano group, or a phenyl group. represents an alkyl group substituted with at least one atom or group of a group, a lower cycloalkyl group, or a lower alkoxyl group. ). ] Aniline derivative represented by. (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.).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 ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ or -S
Represents a group represented by R_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group, or phenyl group, and R_4 represents a lower alkyl group, phenyl group, or lower alkoxycarbonyl group). ] There are compounds represented by the general formula ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [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 -W-R_5 (
Here, W represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, lower alkenyl group, lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or is substituted with a halogen atom. or an alkyl group substituted with at least one atom or group selected from a halogen atom, a cyano group, a phenyl group, a lower cycloalkyl group, or a lower alkoxyl group. ). R_6 represents a halogen atom. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound shown by It has the same meaning as above. ] A method for producing an aniline derivative represented by (3) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.) represents an oxygen atom or a sulfur atom.] A phenyl isocyanate derivative represented by the general formula R_5-W-H [wherein, W represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, a lower alkenyl group, a lower Represents an alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, a cyano group, a phenyl group, or a lower cycloalkyl group. (represents an alkyl group substituted with at least one atom or group among groups or lower alkoxyl groups).] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by ▼ [In the formula, X, Y, k, l, m, n, R_1, A, W and R_5 represent the same meanings as above.] A method for producing an aniline derivative represented by the following. (4) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different, 0 or 1
represents. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables, etc. ▼, -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
2-A'-R_2, -SO_2NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ to represent a group (here, A' and A'' are the same or different and represent an oxygen atom or a sulfur atom) , R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and n represents 0, 1 or 2.) A is oxygen. B represents a lower alkyl group, lower alkenyl group, lower cycloalkyl group, phenyl group, or a substituent represented by the general formula -W-R_5 (here, W
represents an oxygen atom or a sulfur atom, and R_5 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkenyl group, a lower haloalkynyl group, or a lower cycloalkyl group, or even if it is substituted with a halogen atom. It represents a phenyl group, or an alkyl group substituted with at least one atom or group selected from a halogen atom, a cyano group, a phenyl group, a lower cycloalkyl group, or a lower alkoxyl group. ). ] Aniline derivatives represented by the general formula Z'-R_7 [wherein Z' is a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or a general formula ▲ Numerical formula, chemical formula, table, etc. ▼Or-SR_4
represents a group represented by (where R_3 represents a lower alkyl group, lower cycloalkyl group or phenyl group,
R_4 represents a lower alkyl group, phenyl group or lower alkoxycarbonyl group. ), R_7 represents a leaving group. ] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by B represents the same meaning as above. ) A method for producing the aniline derivative shown in (5) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group, and k, l, m and n are the same or Differently, they represent 0 or 1. ] A compound represented by the general formula R_8-R_9 [In the formula, R_8 represents a halogen atom, and R_9 is the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ or ▲ Numerical formulas,
There are chemical formulas, tables, etc. ▼ Represents a substituent shown by , represents a lower haloalkyl group or lower alkoxylalkyl group).] There are general formulas ▲ mathematical formulas, chemical formulas, tables, etc. that are characterized by reacting with the compound represented by ▼ [In the formula, X, Y, k, l, m, n and R_9 have the same meanings as above.] A method for producing an aniline derivative represented by the following. (6) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, X and Y are the same or different and represent a lower alkylene group or a lower alkoxy lower alkylene group. k, l, m and n are the same or different and represent 0 or 1. R_1 is a nitro group, 2-nitrovinyl group, amino group, isothiocyanato group, lower alkylamino group, or general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Mathematical formulas, chemical formulas,
There are tables etc.▼ -NH-S-R_2, -O-S-R_2, -S-A'-
R_2, ▲There are mathematical formulas, chemical formulas, tables, etc.▼, -SO_
Represents a group represented by 2-A'-R_2, -SO_2-NH-R_2 or ▲There are mathematical formulas, chemical formulas, tables, etc. (here, A' and A'' are the same or different, and represent an oxygen atom or a sulfur atom. (R_2 and R'_2 are the same or different and represent a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower haloalkyl group or a lower alkoxyalkyl group, and p represents 0, 1 or 2.).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 ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ or -S
Represents a group represented by R_4 (here, R_3 represents a lower alkyl group, lower cycloalkyl group, or phenyl group, and R_4 represents a lower alkyl group, phenyl group, or lower alkoxycarbonyl group). 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 -W-R_5 (here, W represents an oxygen atom or a sulfur atom, and R_5 is a lower alkyl group) , lower alkenyl group,
Represents a lower alkynyl group, lower haloalkenyl group, lower haloalkynyl group, or lower cycloalkyl group, or represents a phenyl group optionally substituted with a halogen atom, or represents a halogen atom, cyano group, phenyl group, lower cyclo It represents an alkyl group or a lower alkoxyl group substituted with at least one atom or group. ). ] An agricultural and horticultural fungicide characterized by containing an aniline derivative represented by the following as an active ingredient.