JPH0463074B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [1] [In the formula, X represents a methylene group or a single bond.
R ₁ is a lower alkyl group, a lower alkoxyl group,
Indicates a lower alkoxymethyl group, a lower alkoxycarbonyl group, a hydrogen atom, a halogen atom, an acyl group, or a cyano group. Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonylalkyl group, or a general formula

[Formula] or -S-R ₃ (where R ₂ is a lower alkyl group, lower cycloalkyl group, or phenyl group, and R ₃ is a lower alkyl group, phenyl group, or lower alkoxycarbonyl group) ). A represents an oxygen atom or a sulfur atom. B is a lower alkenyl group, or has the general formula W-
Represents a group represented by R ₄ (where W represents an oxygen atom or a sulfur atom. _{R 4} represents a lower alkenyl group, a lower alkynyl group, a lower haloalkynyl group,
Indicates a lower haloalkenyl group, or a lower alkyl group optionally substituted with a halogen atom, cyano group, phenyl group, lower cycloalkyl group, or lower alkoxy group. ). ] The present invention relates to an aniline derivative represented by the following, a method for producing the same, and an agricultural and horticultural fungicide containing the same as an active ingredient. The aniline derivatives represented by the general formula [I] include benomyl [methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamate], fuberidazole [2-(2-furyl)benzimidazole], and thiabendazole [2-(4- thiazolyl) benzimidazole], carbendazim [methyl benzimidazol-2-ylcarbamate], thiophanate methyl [1,2-bis(3
-methoxycarbonyl-2-thioureido)benzene], thiophanate [1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene], benzimidazole/thiophanate fungicides, and procymidone [N-3',5' -dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarpoxiimide], iprodione [3-(3',5'-dichlorophenyl)-1-isopropylcarbamoylimidazolidine-2,4
-dione], vinclozolin [3-(3',5'-dichlorophenyl)-5-methyl-5-vinyl-oxazolidine-2,4-dione], ethyl (RS)-
3(3',5'-dichlorophenyl)-5-methyl-
Showing a strong selective bactericidal effect against plant pathogenic bacteria and other filamentous fungi (hereinafter referred to as drug-resistant bacteria) that exhibit resistance to cyclic imide fungicides such as 2,4-dioxoxazolidine-5-carboxylate. It is characterized by As a result of our earnest efforts to invent a bactericidal agent that exhibits a selective bactericidal effect against drug-resistant bacteria, the present inventors discovered that the aniline derivative represented by the general formula [I] has a strong bactericidal effect selectively against drug-resistant bacteria. It was found that it shows. That is, as is clear from the test examples described later, the compound of the present invention has no control effect on diseases caused by wild bacteria that are susceptible to benzimidazole thiophanate fungicides or cyclic imide fungicides (hereinafter referred to as drug-susceptible bacteria). However, it showed an excellent control effect against diseases caused by drug-resistant bacteria, and the bactericidal activity of the compound of the present invention against drug-resistant bacteria was extremely selective. As mentioned above, the compound of the present invention exhibits a strong bactericidal effect selectively against bacteria that are resistant to benzimidazole/thiophanate fungicides, and therefore, it is expected that the compounds will appear or have appeared as a result of the use of the above-mentioned fungicides. It can be used to control resistant bacteria. For example, powdery mildew (Podosphaera leoucotricha), Venturia inaequalis on apples, Venturia nashicola and Sclerosinia mali on pears, Gloeosporium kaki on oysters, and Gray blight on peaches ( Sclerotinia cinerea), Cladosporium carpophilum, Botrytis cinerea, Eisinoe ampelina, Glomerella
cingulata), sugar beet brown spot fungus (Cercaspora
beticala), peanut brown spot fungus (Cercospora
arachidicola), Cercospora
personata), powdery mildew of barley (Erysiphe graminis f.sp.hoedei), eye spot fungus (Cercosporella herpotrichoides), red snow rot fungus (Fusarium nivale), powdery mildew of wheat (Erysiphe graminis f.sp.tritici) , powdery mildew of cucumber (Sphaerotheca
fuliginea), vine blight fungus (mycosphaerella)
melonis), Botrytis cinerea,
Cladosporium cucumerinum, tomato leaf mold (Cladosporinum fulvum), botrytis cinerea, strawberry powdery mildew (Sphaerotheca humuli), hop botrytis cinerea, tobacco powdery mildew It can be used to control drug-resistant bacteria such as Erysiphe cichoracearum, Diplocarpon rosae, Elsinoe fawcetii, Penicillium italicum, and Penicillium digitatum. can. As a result of further studies, it was found that the compound of the present invention is effective in controlling rice blast fungi (Pyricularia oryzae), etc., regardless of the presence or absence of drug resistance. The compound of the present invention can be produced, for example, by the following method. Manufacturing method (a) General formula [] [In the formula, X, R ₁ and Z have the same meanings as above. ] Compounds shown by and general formula [] [In the formula, A and B represent the same meanings as above, and R ₅ represents a halogen atom. ] A manufacturing method of reacting with a compound represented by: This reaction is carried out, for example, in water or an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, chloroform, carbon tetrachloride, ethyl acetate, pyridine, dimethylformamide, or a mixture thereof, usually pyridine, triethylamine,
N,N-diethylaniline, sodium hydride,
This can be carried out in high yield using a deoxidizing agent such as potassium hydroxide and, if necessary, a phase transfer catalyst such as tetrabutylammonium bromide.
Cool or heat the reaction (0 to 150℃) as necessary.
By doing so, the process can be completed within 10 hours and the desired product can be obtained in good yield. Incidentally, the compound represented by the general formula [] can be obtained by the following method. When the substituent Z is a hydrogen atom in the compound represented by the general formula [], the general formula [] [In the formula, X represents the same meaning as above. ] It can be obtained by reducing the nitrobenzene derivative shown below. For example, a method of reduction using sodium sulfide or sodium hydrosulfide in a mixture of water and a lower alcohol such as methanol or ethanol can be used. The reaction is usually completed within 12 hours at a temperature range from 50°C to the solvent reflux temperature. Alternatively, it can be carried out by a method using iron powder, zinc powder, or tin powder in a mixture of water and an inorganic acid such as acetic acid, hydrochloric acid, or sulfuric acid. The reaction is usually carried out at 50°C to 100°C and is completed within 12 hours.
Furthermore, it is possible to use a method of hydrogenation in an organic solvent such as ethanol or ethyl acetate using a catalyst such as platinum dioxide or palladium-carbon under normal pressure or pressure, usually at 0 to 60°C. The nitrobenzene derivative represented by the general formula [] can be easily synthesized, for example, by the method described in the literature (J.Chem.Soc., 1933 , 699). In addition, the compound represented by the general formula [] has a substituent Z
When is other than a hydrogen atom, the general formula obtained as above [] [In the formula, and R ₁ have the same meanings as above. ] A compound 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

[Formula] or -S-R ₃ (where R ₂ is a lower alkyl group, lower cycloalkyl group, or phenyl group, and R ₃ is a lower alkyl group, phenyl group, or lower alkoxycarbonyl group) ).
R ₇ represents a leaving group. ] It can be obtained by reacting the compound shown below. Examples of the leaving group include a halogen atom, a tosyloxy group, and a mesyloxy group. Compounds represented by general formula [] and general formula []
For example, the condensation reaction with a compound represented by N,
in an organic solvent such as N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, dioxane, toluene, benzene, ether, or
In a two-layer reaction system of toluene or benzene and water, using a deoxidizing agent such as sodium hydroxide, potassium carbonate, sodium hydride, N,N-diethylaniline, or pyridine as necessary, the reaction can be carried out without a catalyst or with tetra- This can be carried out in the presence of a phase transfer catalyst such as n-butylammonium bromide. The reaction is usually completed within 12 hours at 0°C to 100°C. Furthermore, in the aniline derivative represented by the general formula [], Z represents a hydrogen atom, and B represents the general formula -
When the group represented by W-R ₄ is represented, the compound of the present invention can be produced, for example, by the following method. Manufacturing method (b) General formula [] [In the formula, X and R ₁ have the same meanings as above. ] A phenyl isothiocyanate derivative represented by the general formula [] R ₄ -W-H [] [wherein R ₄ and W represent the same meanings as above. ] A manufacturing method of reacting with a compound represented by: This reaction is carried out, for example, without a solvent or in an organic solvent such as benzene, toluene, xylene, diethyl ether, tetrahydrofuran, dioxane, N,N-dimethylformamide, chloroform, or carbon tetrachloride, without a catalyst, or with triethylamine, N,
This can be carried out using N-diethylaniline or 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 within 10 hours and the desired product can be obtained in good yield. The phenyl isothiocyanate derivative represented by the general formula [ ] can be obtained by reacting the compound represented by the general formula [ ] with phosgene or thiophosgene. This reaction is carried out in an organic solvent such as benzene, toluene, xylene, ethyl acetate or a mixture thereof. The reaction can be completed within 10 hours by heating from 50° C. to reflux temperature as necessary, and the desired product can be obtained in good yield. Furthermore, when Z in the aniline derivative represented by the above general formula [] is other than a hydrogen atom, the compound of the present invention can be produced, for example, by the following method. Manufacturing method (c) General formula obtained according to the above manufacturing method (a) or (b) [] [In the formula, X and B represent the same meanings as above. ] A manufacturing method in which a compound represented by these and a compound represented by the general formula [] are reacted. This condensation reaction is usually carried out without a catalyst or with tetra-n-butylammonium bromide in an organic solvent such as N,N-dimethylformamide, dimethyl sulfoxide, ether, or tetrahydrofuran using a base such as potassium hydroxide or sodium hydride. This can be carried out in the presence of a phase transfer catalyst such as. The reaction is usually completed within 12 hours at a temperature of 0°C to 100°C. Next, a manufacturing example will be shown. Production Example 1 [According to production method (a). ] 6-amino-8-chloro-1,3-benzodioxane 1.0g, N,N-diethylaniline 0.85g,
0.70 g of isopropyl chloroformate was added dropwise to 15 ml of toluene mixed solution over 5 minutes under ice cooling.
After the reaction solution was left at room temperature for 12 hours, it 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 benzene and tetrahydrofuran, and purified with isopropyl N-
(8-chloro-1,3-benzodioxysan-6
-il) carbamate 1.35 g were obtained. (Yield 92%) Melting point 126-128°C Production Example 2 [According to production method (b). ] 6-Amino-8-ethquin-1,3-benzodioxane (1.95 g) was dissolved in 20 ml of toluene and added dropwise to a toluene solution containing 10 g of phosgene at 10 to 20°C. After gradually heating and refluxing for 30 minutes, the temperature was returned to room temperature, the solvent was distilled off under reduced pressure, and 8-ethoxy-1,
3-Benzodioxan-6-yl isocyanate was obtained. Without purification, this was added dropwise to 50 ml of toluene solution containing 1.0 g of triethylamine and 0.70 g of 2-fluoroethanol at room temperature. After being left at room temperature for 12 hours, it was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate.
Fluoroethyl N-(8-ethoxy-1,3-
benzodioxan-6-yl) carbamate
Obtained 2.31g. (Yield 80.9%) Melting point 154-154.5°C Production Example 3 [According to production method (c). ] 0.107g of sodium hydride (60% oily) in N,N
-Isopropyl N-(8-ethoxy-
0.75 g of 1,3-benzodioxan-6-yl) carbamate was added. After stirring at room temperature for 1 hour,
To this was added 0.39 g of phenylsulfenyl chloride under ice cooling. After stirring at room temperature overnight, the reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and ethyl acetate to obtain isopropyl N-phenylthio-N-(8-ethoxy-1,3-benzodioxane-6). -il) carbamate 0.91 g was obtained. (Yield: 87.5%) Melting point: 120-123°C The compounds of the present invention thus obtained are illustrated in Table 1.

【table】

【table】

[Table] When actually applying the compound of the present invention obtained in this way, it can be used as it is without adding other ingredients, or it can be mixed with a carrier and applied to make it easier to use as a fungicide. Commonly used forms such as powders, wettable powders, oils, emulsions, tablets,
It is formulated into granules, microgranules, aerosols, flowables, etc. and applied. Examples of formulations are shown below. Formulation Example 1 Powder 2 parts of the compound of the present invention (15), 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 30 parts of the compound of the present invention (24), 45 parts of diatomaceous earth, 20 parts of white carbon, wetting agent (sodium lauryl sulfate)
3 parts and 2 parts of a dispersant (calcium lignin sulfonate) are thoroughly ground and mixed to obtain a wettable powder having a base ingredient content of 30%. Formulation Example 3 Wettable powder 50 parts of the compound of the present invention (25), 45 parts of diatomaceous earth, 2.5 parts of wetting agent (calcium alkylbenzenesulfonate) and dispersant (calcium ligninsulfonate)
Thoroughly grind and mix 2.5 parts to obtain a hydrating agent with a base ingredient content of 50%. Formulation Example 4 Emulsion 10 parts of the compound of the present invention (26), 80 parts of cyclohexanone
1 part and 10 parts of an emulsifier (polyoxyethylene alkyl allyl ether) to obtain an emulsion with a base agent content of 10%. The active compounds in the above formulations are generally expressed by weight.
It contains 1.0 to 95.0%, preferably 2.0 to 80.0%, and the application amount is usually 10 to 100 g per 10 are.
Further, it is preferable that the concentration used is 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 do not limit yourself to the above range. There is no problem in increasing or decreasing the amount without any problem. 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】

【table】

[Table] Note (1) Commercially available herbicide Note (2) Commercially available 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 in accordance with Formulation Example 4 was sprayed onto 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). After cultivating this in a greenhouse for 10 days to develop the 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, 0,
The disease was classified into indexes of 0.5, 1, 2, and 4, and the 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. Disease severity (%) = Σ {(Sickness index) x (Number of leaves)}/(Number of inspected leaves) x 4 x 100 Subsequently, the control value was calculated from 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.

[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. After 20 days of cultivation in a greenhouse, 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 applied to the seedlings obtained after 20 days of cultivation in a greenhouse 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 calculation of control value 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】

[Table] Test Example 3 Pear scab control effect A 90ml plastic pot was filled with mixed soil of peat moss and sandy loam, and pear fruit (variety:
Seeds collected from Chojuro) were sown. This was cultivated in a greenhouse for 20 days, and a water diluted solution of the emulsion of the present compound and the hydrating agent of the control compound below, prepared according to Formulation Example 4, was applied to the seedlings so that droplets sufficiently adhered to the leaf surface. Sprayed on leaves and foliage. After the chemical solution was air-dried, the seedlings were spray-inoculated with a conidial suspension of Venturia nashicola, which is either resistant or susceptible to the drug. 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】

[Table] Test Example 4 Peanut brown spot control effect A 100 ml plastic pot was filled with sandy loam soil, 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 inoculated by spraying 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. 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 described below were sprayed onto the foliage of the seedlings at 10 ml per pot.
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 showed a pesticidal effect.

【table】

[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 young seedlings, 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 the foliage of each pot. After air-drying the chemical solution, seedlings are infected with drug-resistant or susceptible cucumber vine blight fungus (Mycosphaerella
Inoculation was carried out by gluing a cut plate (diameter 5 mm) of M. melonis on the leaf surface. 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 showed a pesticidal effect.

【table】

[Table] Test Example 7 Effect on controlling citrus blue mold disease After thoroughly washing citrus fruit (variety: Unshu) with water and air drying, the following emulsion of the compound of the present invention prepared according to Formulation Example 4 and the following control commercially available drug were diluted with water. The sample was immersed in a chemical solution with a predetermined concentration for 1 minute. After air-drying, conidia of drug-resistant or sensitive citrus blue mold fungus (Penicillium italicum) were suspended in water and sprayed onto the fruit surface. After being kept in a greenhouse 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 status) (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 showed a pesticidal effect.

[Table] Test Example 8 Phytotoxicity test 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 below and a hydrating powder of the control compound 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 abnormality. + 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.

【table】

Claims (1)

[Claims] 1. General formula [In the formula, X represents a methylene group or a single bond.
R ¹ is a lower alkyl group, a lower alkoxyl group,
Indicates a lower alkoxymethyl group, a lower alkoxycarbonyl group, a hydrogen atom, a halogen atom, an acyl group, or a cyano group. Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or the general formula -
Represents a group represented by C(O) _-R2 or -S- _R3 (where _R2 represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group, and _R3 represents a lower alkyl group, a phenyl group, or lower alkoxycarbonyl group). A represents an oxygen atom or a sulfur atom. B is a lower alkenyl group, or the general formula -
WR represents a group represented by ₄ (where W represents an oxygen atom or a sulfur atom; R ₄ represents a lower alkenyl group, a lower alkynyl group, a lower haloalkynyl group, a lower haloalkenyl group, or a halogen atom,
Indicates a lower alkyl group optionally substituted with a cyano atom, phenyl group, lower cycloalkyl group, or lower alkoxy group. ). ] Aniline derivative represented by. 2 General formula [In the formula, X represents a methylene group or a single bond.
R ¹ is a lower alkyl group, a lower alkoxyl group,
Indicates a lower alkoxymethyl group, a lower alkoxycarbonyl group, a hydrogen atom, a halogen atom, an acyl group, or a cyano group. Z is a hydrogen atom, a lower alkyl group, a lower alkenyl group, a lower alkynyl group, a lower alkoxycarbonyl alkyl group, or the general formula -
Represents a group represented by C(O) _-R2 or -S- _R3 (where _R2 represents a lower alkyl group, a lower cycloalkyl group, or a phenyl group, and _R3 represents a lower alkyl group, a phenyl group, or lower alkoxycarbonyl group). A represents an oxygen atom or a sulfur atom. B is a lower alkenyl group, or the general formula -
WR represents a group represented by ₄ (where W represents an oxygen atom or a sulfur atom; R ₄ represents a lower alkenyl group, a lower alkynyl group, a lower haloalkynyl group, a lower haloalkenyl group, or a halogen atom,
Indicates a lower alkyl group optionally substituted with a cyano atom, phenyl group, lower cycloalkyl group, or lower alkoxy group. ). ] An agricultural and horticultural fungicide characterized by containing an aniline derivative represented by the following as an active ingredient.