A carbazole alkaloid derivative and its application

Abstract

The present invention belongs to the field of pesticide synthesis technology and provides a carbazole compound and its preparation method and application. The structural formula of the carbazole compound FMCc6 is: #imgabs0#. The compound is used to control Rhizoctonia solani ( Rhizoctonia solani ), Alternaria alternata ( Alternaria alternate ) or Pyricularia oryzae ( Pyricularia oryzae This compound has excellent commercial application prospects and is suitable for industrial production. This carbazole compound can also serve as a lead compound, further enhancing its biological activity through structural modification, and serve as an important source for drug development.

Description

Technical Field

[0001] The invention belongs to the technical field of pesticide synthesis and relates to a carbazole compound and a preparation method and application thereof. Background Art

[0002] The disclosure of this background information is intended to enhance understanding of the general background of the invention and should not necessarily be regarded as an acknowledgment or any form of suggestion that this information constitutes the prior art already known to a person skilled in the art.

[0003] Plant fungal diseases are a major source of crop infection, causing a variety of plant diseases, leading to reduced yields and quality. Globally, fungal diseases cause 10%-15% of crop losses annually, resulting in direct economic losses amounting to hundreds of billions of dollars. Tobacco and rice, important cash and food crops in my country, are threatened by a variety of fungal diseases throughout their growth cycles, such as tobacco target spot, tobacco brown spot, and rice blast, which severely hinder the stable development of tobacco and rice production.

[0004] Currently, the use of chemical agents is the primary means of controlling plant fungal diseases. However, due to the long-term and extensive use of fungicides, pathogens have significantly developed resistance to existing fungicides, resulting in a decrease in the effectiveness of many commercial fungicides against diseases. Therefore, the development of novel, highly effective, and environmentally friendly compounds for the control of plant fungal diseases is of great significance.

[0005] Natural products, due to their novel structures and unique mechanisms of action, are an important source for drug development. Carbazole alkaloids, primarily found in plants of the Rutaceae family, are an important class of nitrogen-containing heterocyclic compounds. Due to their stable structures and diverse substitution positions, they are used in pharmaceutical, industrial, and agrochemical applications for anticancer, antibacterial, antimalarial, and antiviral properties. In agriculture, some carbazole derivatives have also demonstrated excellent insecticidal and antiviral activity. Therefore, the development of carbazole alkaloid derivatives holds promise for providing novel lead compounds for the prevention and treatment of plant fungal diseases. Summary of the Invention

[0006] In order to further develop agents for preventing and treating plant fungal diseases, the present invention provides a carbazole compound having good biological activity against the main pathogenic fungi of tobacco and rice.

[0007] Another object of the present invention is to provide a method for synthesizing the above-mentioned carbazole compounds, which has a short synthesis process and has industrial prospects.

[0008] Another object of the present invention is to provide a use of the above-mentioned carbazole compound in the preparation of agricultural fungicides.

[0009] To achieve the above objectives, the present invention adopts the following technical solutions.

[0010] A carbazole compound, referred to as FMCc6, has the structural formula:

[0011] .

[0012] A method for preparing the above-mentioned carbazole compound comprises the following steps:

[0013] (1) Indole, bromoacetaldehyde diethyl acetal, and ethyl acetoacetate react in an organic solvent in the presence of ZnCl2 to obtain ;

[0014] (2) React in a strong alkaline environment and obtain after acidification ;

[0015] (3) The target product was obtained by reacting 2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate with 4-fluorophenylethylamine in an organic solvent under the catalysis of HATU (2-(7-azabenzotriazole)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and DIPEA (N,N-diisopropylethylamine).

[0016] In step (1), the reaction temperature is 60°C; in step (2), the reaction temperature is 70°C.

[0017] In step (2), the strongly alkaline environment is an ethanol-water solution in which KOH is dissolved, and the volume ratio of the ethanol to water is 3:1.

[0018] In step (1), the organic solvent is ethanol; in step (3), the organic solvent is DMF (N,N-dimethylformamide).

[0019] The present invention also provides a use of the above-mentioned carbazole compound FMCc6 as an agricultural fungicide.

[0020] The present invention also provides a fungicide composition comprising the aforementioned carbazole compound FMCc6. The carbazole compound FMCc6 is present in the fungicide composition as an active ingredient in an amount ranging from 0.1 wt% to 99 wt%, preferably from 1 to 80 wt%, and more preferably from 5 to 50 wt%.

[0021] The control target of the agricultural fungicide or fungicide composition is Rhizoctonia solani ( Rhizoctonia solani ), Alternaria alternata ( Alternaria alternate ) or Pyricularia oryzae ( Pyricularia oryzae ).

[0022] The crops controlled by the agricultural fungicide or fungicide composition are selected from tobacco or rice.

[0023] The fungicidal composition may further comprise other inert ingredients for stabilizing the active ingredients and facilitating their application to crops or attachment to targets, such as fillers, wetting agents, dispersants, defoaming agents, antifreeze agents, solvents, emulsifiers, preservatives, disintegrants, pigments, and the like.

[0024] The above composition can be processed by the methods commonly used in the prior art. Preferred dosage forms include suspensions, granules, wettable powders, water-dispersible granules, emulsifiable concentrates, aqueous emulsions, and microemulsions.

[0025] Preferably, the formula of the suspension concentrate is: 5%-50% FMCc6 technical, 1%-8% wetting and dispersing agent, 0.05%-1% thickener, 0.1%-0.3% defoaming agent, 1%-3% antifreeze agent, 0.1%-0.5% preservative, and water to 100%; wherein the dispersant is selected from polycarboxylates, methyl acrylates, lignin sulfonates, naphthalenesulfonate formaldehyde condensates, and polyvinyl pyrrolidones; the wetting agent is selected from fatty alcohol block polyethers, polyoxyethylene sorbitan fatty acid esters, and sorbitan fatty acid esters; the thickener is selected from magnesium aluminum silicate, xanthan gum, and white carbon black; the defoaming agent is selected from silicones; the antifreeze agent is selected from polyols, such as ethylene glycol, propylene glycol, and glycerol; and the preservative is selected from isothiazolinones and sodium benzoate.

[0026] The raw materials are added sequentially to a reactor according to the above suspension concentrate formulation, mixed thoroughly, and subjected to high-speed shearing, wet grinding, and finally homogenized filtration to produce an aqueous suspension concentrate. The main technical specifications for the suspension concentrate are: a suspension rate of no less than 90%, a pH of 4-8, a sustained foaming capacity of no more than 50 mL (after 1 minute), a 75 μm wet sieve pass rate of no less than 98%, and acceptable pourability, cold storage stability, and hot storage stability as determined according to GB / T 37137, GB / T 19136, and GB / T 19137.

[0027] Preferably, the water-dispersible granules have a formulation of: 1%-80% FMCc6 technical, 3%-12% dispersant, 1%-10% wetting agent, 1%-10% disintegrant, 0%-8% binder, and filler to 100%. The dispersant is selected from carboxylates, lignin sulfonates, and alkylnaphthalene sulfonate polycondensates, such as GY-D800, Dispersol PSR 19, and DM04. The wetting agent is selected from one or more combinations of polycarboxylates, anions, such as sodium dodecyl sulfonate, and alkylnaphthalene sulfonate formaldehyde condensates. The disintegrant is selected from one or more combinations of urea, inorganic salts, and sucrose, such as wgwin D909S, sucrose, ammonium sulfate, and urea. The binder is selected from one or more combinations of polyethylene glycol 6000, modified polyvinyl alcohol, and carboxymethyl cellulose. The filler is selected from corn starch or diatomaceous earth.

[0028] The raw materials are mixed evenly according to the above-mentioned water-dispersible granule formulation, subjected to airflow milling, and then blended to produce a coarse powder. An appropriate amount of water is then added for kneading and granulation. The main equipment includes a mixer, airflow mill, granulator, and dryer. The key technical specifications for water-dispersible granules are: suspension rate of no less than 80%, dispersibility of no less than 80%, wetting time of no more than 90 seconds, 75 μm wet sieve pass rate of no less than 98%, sustained foaming of no more than 60 mL (after 1 minute), pH 4-9, and acceptable thermal storage stability as determined according to GB / T 19137.

[0029] Preferably, the formula of the wettable powder is: 1%-90% FMCc6 technical, 3%-15% dispersant, 2%-10% wetting agent, and filler to 100%; wherein the dispersant is selected from carboxylates, alkylnaphthalenesulfonate polycondensates, such as one or a combination of GY-D800, Dispersol PSR 19, and Dispersol BB4; the wetting agent is selected from anionic wetting agents, such as one or a combination of GY-WS01 and Multiwet 8269; and the filler is selected from one or a combination of kaolin and corn starch.

[0030] The materials are mixed uniformly according to the above wettable powder formulation ratio, subjected to airflow milling, and then mixed to produce a wettable powder. The main technical specifications of the wettable powder are: suspension rate of not less than 75%, wetting time of not more than 120 seconds, 45 μm wet sieve pass rate of not less than 95%, moisture content of not more than 3%, pH 4-9, and qualified thermal storage stability as determined according to GB / T 19137.

[0031] Preferably, the formula of the emulsifiable concentrate is: 20%-50% FMCc6 technical, 1%-10% emulsifier, and solvent supplemented to 100%; wherein the emulsifier is selected from one or more combinations of Nong Ru 500#, Nong Ru 400#, Nong Ru 600#, and Atlox 4838B; and the solvent is selected from one or a combination of solvent oil S150 and mineral oil.

[0032] According to the above-mentioned EC formulation, the technical drug and emulsifier are dissolved in a solvent, mixed according to the formula, and allowed to stand for filtration. The main equipment is a stirred tank. The EC's key technical specifications are: moisture content no greater than 2%, sustained foaming no greater than 60 mL (after 1 minute), pH 4-8, and compliance with 200-fold dilution emulsion stability, cold storage stability, and hot storage stability as determined by methods in accordance with GB / T 1603, GB / T 19136, and GB / T 19137.

[0033] Preferably, the microemulsion has the following formula: 0.5%-60% FMCc6 technical, 3%-20% emulsifier, 1%-30% solvent, 0%-5% cosolvent, and water to 100%; the emulsifier is selected from anionic phosphates, such as Atplus 310; the solvent is selected from one or more combinations of xylene, cyclohexanone, and dimethylformamide; and the cosolvent is selected from n-butanol or n-pentanol.

[0034] Mix all ingredients except water according to the microemulsion formula, stirring until completely dissolved. Add water and stir using a high-speed shear emulsifier until the mixture is clear and transparent. Key technical specifications for the microemulsion include: a satisfactory transparency temperature range (0-50°C), sustained foaming of no more than 30 mL (after 1 minute), a pH of 4-8, and satisfactory emulsion stability at 200x dilution, cold storage stability, and hot storage stability as determined by methods in accordance with GB / T 1603, GB / T 19136, and GB / T 19137.

[0035] The endpoints of the ranges and any values ​​disclosed in this application are not limited to the precise ranges or values, and these ranges or values ​​should be understood to include values ​​close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values ​​can be combined with each other to obtain one or more new numerical ranges, and these numerical ranges should be considered to be specifically disclosed in this application.

[0036] The present invention has the following advantages:

[0037] The carbazole compounds provided by the present invention can inhibit the mycelial growth of tobacco target spot pathogen, tobacco brown spot pathogen, rice sheath blight pathogen, and rice blast pathogen at relatively low concentrations, outperforming the commercially available agent, Jinggangmycin. They can be used to prepare pesticides for controlling these diseases and have excellent commercial application prospects. The carbazole compounds provided by the present invention have a short synthesis process, simple purification, and high yield, making them suitable for industrial production. The carbazole compounds provided by the present invention can also serve as lead compounds, with their biological activity further enhanced through structural modification, making them an important source for drug development. BRIEF DESCRIPTION OF THE DRAWINGS

[0038] Figure 1 For the carbazole compound FMCc6 1 H NMR spectrum;

[0039] Figure 2 For the carbazole compound FMCc6 13 C NMR spectrum;

[0040] Figure 3 For the carbazole compound FMCc6 19 F NMR spectrum;

[0041] Figure 4 This is the HRMS spectrum of the carbazole compound FMCc6. DETAILED DESCRIPTION

[0042] The present invention will be further described below with reference to the examples, but the present invention is not limited by the following examples.

[0043] Example 1 Preparation of carbazole compound FMCc6

[0044] (1) Synthesis of 1a

[0045]

[0046] In a clean 100 mL conical flask, indole (S0, 10 mmol), bromoacetaldehyde diethyl acetal (10 mmol), ethyl acetoacetate (10 mmol), and ethanol (30 mL) were added in sequence. Then, ZnCl2 (1.0 mol) was added to the above reaction mixture. The reaction was stirred at 60°C for 2 h to obtain intermediate 1a.

[0047] (2) Synthesis of 2a

[0048]

[0049] Intermediate 1a (5.0 mmol) was dissolved in a solution of KOH (15.0 mmol) in EtOH / H2O (3:1) (20 mL), stirred at 70°C for 6 h, and then acidified with dilute hydrochloric acid to obtain intermediate 2a.

[0050] (3) Synthesis of FMCc6

[0051]

[0052] Intermediate 2a (2 mmol) was dissolved in 15 mL of dry DMF. 4-Fluorophenylethylamine (2 mmol) was added, followed by HATU (3.3 mmol) and DIPEA (15 mmol). The reaction mixture was allowed to react at room temperature for 8 h. A yellow solid was obtained with a yield of 87%.

[0053] The product 1 H NMR, 13 C NMR, 19 F NMR and HRMS analysis, the spectra are as follows Figure 1-Figure 4 As shown; the analysis is as follows:

[0054] 1 H NMR (600 MHz, DMSO- d 6 , 25℃) δ = 11.27 (s, 1H), 8.29 (t, J = 5.5 Hz,1H), 8.11 (d, J = 7.8 Hz, 1H), 7.95 (d, J = 8.0 Hz, 1H), 7.53 (d, J = 8.1 Hz, 1H),7.41 (t, J = 7.6 Hz, 1H), 7.33 (dd, J = 8.1, 5.9 Hz, 2H), 7.19 - 7.12 (m, 3H),7.09 (d, J = 8.0 Hz, 1H), 3.52 (dd, J = 13.0, 6.8 Hz, 2H), 2.88 (t, J = 7.1 Hz,2H), 2.49 (s, 3H) ppm;

[0055] 13 C NMR (151 MHz, DMSO- d 6 , 25℃) δ = 169.7, 162.5, 160.1, 140.9, 139.7,136.2 (d, J = 4.5 Hz), 134.6, 131.02 (d, J = 12.0 Hz), 126.3, 122.9, 121.0,118.6, 118.5, 118.4 (d, J = 246.1 Hz), 115.5, 115.3, 111.6, 40.9, 34.6, 14.6ppm;

[0056] 19 F { 1 H} NMR (565 MHz, DMSO- d 6 , 25℃) δ = -117.3. MS (ESI) m / z 347.2 = [M+ H] + , HRMS m / z 347.1559 = [M + H] + , calcd. for C 22 H 20 FN2O m / z = 347.1554.

[0057] From the above, we can see that the structural formula of FMCc6 is: .

[0058] Example 2 Indoor toxicity of carbazole compound FMCc6 against pathogenic bacteria

[0059] The mycelial growth rate method was used to determine the indoor toxicity of the carbazole derivative FMCc6 against major tobacco and rice pathogenic fungi. The specific process is as follows:

[0060] (1) Isolation of pathogenic strains

[0061] Diseased leaves with obvious symptoms of the pathogen were collected from the main tobacco and rice producing areas in Jiangxi Province and the strain was isolated and purified using the water agar method. After purification for 5 times, the tobacco target spot pathogen ( Rhizoctonia solani )、Tobacco brown spot pathogen ( Alternaria alternate ), Rice Sheath Blight Pathogen ( Rhizoctonia solani ) and rice blast fungus ( Pyricularia oryzae ) 4 pathogens for subsequent indoor virulence testing of compounds.

[0062] (2) Preparation of drug-containing culture medium

[0063] Accurately weigh the carbazole alkaloid derivative FMCc6 and dissolve it in DMSO to prepare a stock solution. This stock solution was then diluted to the target concentration with 0.1% Tween-80 aqueous solution. The dilution and sterilized PDA medium were mixed at a volume ratio of 1:9 (drug solution: medium) to prepare a drug-containing medium with a target concentration of 20 μg / mL. The same volume of 0.1% Tween-80 was added to the blank control. The commercial agent, 24% aqueous solution of validamycin, was directly diluted to the target concentration with 0.1% Tween-80 aqueous solution.

[0064] (3) Toxicity assay

[0065] Virulence was determined using the hyphae growth rate method. The test bacteria were inoculated onto PDA plates and pre-cultured for 5 days. A 5 mm diameter punch was used to punch a bacterial cake at 1 / 3 of the colony edge. The cake was then transferred to drug-containing and blank PDA medium, respectively, and cultured in a 28°C constant temperature incubator for 3 days. Each treatment was repeated three times. When the hyphae of the blank control filled 2 / 3 of the culture medium, the colony diameter was measured using the cross-hatch method. The average value was calculated and compared with the control. The inhibitory rate of the compound against the hyphae was calculated according to the following formula:

[0066] .

[0067] Table 1 Results of indoor toxicity tests of the carbazole derivative FMCc6 against four pathogenic fungi

[0068]

[0069] The results in Table 1 indicate that compound FMCc6 exhibits broad-spectrum antifungal activity, demonstrating strong inhibitory activity against a variety of plant pathogens, including tobacco target spot, tobacco brown spot, and rice blast. At the same concentration, compound FMCc6 exhibited superior inhibitory activity against all four pathogens, including tobacco target spot, tobacco brown spot, rice sheath blight, and rice blast, compared to the commercially available agent, Jinggangmycin. In summary, the carbazole compound FMCc6 possesses significant application potential and development value.

[0070] Example 3 Preparation of FMCc6 Preparation

[0071] 1. Suspension

[0072] FMCc6 technical 5%-50%, dispersant 2%-5%, wetting agent 1%-3%, thickener 0.05%-1%, defoamer 0.1%-0.3%, antifreeze 1%-3%, preservative 0.1%-0.5%, water to 100%;

[0073] The dispersant is selected from polycarboxylates, methyl acrylates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, and polyvinyl pyrrolidone;

[0074] The wetting agent is selected from fatty alcohol block polyether, polyoxyethylene sorbitan fatty acid ester, and sorbitan fatty acid ester;

[0075] The thickener is selected from magnesium aluminum silicate, xanthan gum, and white carbon black;

[0076] The defoaming agent is selected from silicone;

[0077] The antifreeze agent is selected from polyols such as ethylene glycol, propylene glycol, and glycerol;

[0078] The preservative is selected from isothiazolinones and sodium benzoate.

[0079] For example, the raw materials can be weighed according to the following formula:

[0080] The content of FMCc6 technical is 10%; the dispersants are carboxylates and lignin sulfonates, with the dosages of 3% and 2% respectively; the wetting agent is EO / PO block copolymer, with the dosage of 1.5%; the thickeners are magnesium aluminum silicate and xanthan gum, with the dosages of 0.5% and 0.05% respectively; the defoaming agent is silicone composite, GY-X60, with the dosage of 0.15%; the antifreeze agent is ethylene glycol, with the dosage of 3%; the preservative is kason, with the dosage of 0.1%; and the balance is water.

[0081] The raw materials are placed in the reactor in sequence according to the formula ratio, mixed evenly, and then subjected to high-speed shearing, wet grinding, and finally homogenized filtration to obtain the product. The main equipment includes a batching kettle, a sand mill, etc.

[0082] Main technical indicators of suspension concentrate: suspension rate not less than 90%, pH 4-8, persistent foaming not more than 50 mL (after 1 minute), 75 μm wet sieve pass rate not less than 98%, pourability, cold storage stability and hot storage stability measured according to GB / T 37137, GB / T 19136 and GB / T 19137 methods are qualified.

[0083] 2. Wettable powder

[0084] FMCc6 technical 1%-90%, dispersant 3%-15%, wetting agent 2%-10%, filler to 100%;

[0085] The dispersant is selected from carboxylates, alkylnaphthalene sulfonate polycondensates, such as one or more combinations of GY-D800, Dispersol PSR 19, and Dispersol BB4;

[0086] The wetting agent is selected from anionic wetting agents, such as one or a combination of GY-WS01 and Multiwet 8269;

[0087] The filler is selected from kaolin, corn starch or a combination thereof.

[0088] The above substances are mixed evenly according to the formula ratio, and then jet milled and mixed to obtain wettable powder. The main equipment includes mixer, jet mill, etc.

[0089] The main technical indicators of wettable powder are: suspension rate not less than 75%, wetting time not more than 120 s, 45 μm wet sieve pass rate not less than 95%, moisture content not more than 3%, pH 4-9, and qualified thermal storage stability determined according to GB / T 19137 method.

[0090] 3. Water dispersible granules

[0091] FMCc6 technical material 1%-80%, dispersant 3%-12%, wetting agent 1%-10%, disintegrant 1%-10%, binder 0%-8%, and filler to 100%;

[0092] The dispersant is selected from carboxylates, lignin sulfonates, and alkylnaphthalene sulfonate polycondensates, such as GY-D800, Dispersol PSR 19, and DM04. The wetting agent is selected from one or more combinations of polycarboxylates, anions, such as sodium lauryl sulfonate, and alkylnaphthalene sulfonate formaldehyde condensates;

[0093] The disintegrant is selected from one or more combinations of urea, inorganic salts, sucrose, such as wgwin D909S, sucrose, ammonium sulfate, and urea;

[0094] The binder is selected from one or more combinations of polyethylene glycol 6000, modified polyvinyl alcohol, and carboxymethyl cellulose;

[0095] The filler is selected from corn starch or diatomaceous earth.

[0096] The above materials are mixed evenly according to the formula ratio, and then mixed to obtain coarse powder after air flow crushing. Then, appropriate amount of water is added to knead and granulate. The main equipment includes mixer, air flow crusher, granulator, dryer, etc.

[0097] The main technical indicators of water-dispersible granules are: suspension rate not less than 80%, dispersibility not less than 80%, wetting time not more than 90 s, 75 μm wet sieve pass rate not less than 98%, persistent foaming not more than 60 mL (after 1 min), pH 4-9, and qualified thermal storage stability determined according to GB / T19137 method.

[0098] 4. EC

[0099] FMCc6 technical 20%-50%, emulsifier 1%-10%, solvent to 100%;

[0100] The emulsifier is selected from one or more combinations of Nongru 500#, Nongru 400#, Nongru 600#, and Atlox 4838B;

[0101] The solvent is selected from solvent oil S150, mineral oil or a combination thereof;

[0102] Dissolve the original drug and emulsifier in a solvent, mix them according to the formula, let them stand and filter. The main equipment is a stirred tank.

[0103] Main technical indicators of emulsifiable concentrate: moisture content not more than 2%, persistent foaming not more than 60 mL (after 1 minute), pH 4-8, and 200-fold diluted emulsion stability, cold storage stability, and hot storage stability measured according to GB / T 1603, GB / T 19136, and GB / T 19137.

[0104] 5. Microemulsion

[0105] FMCc6 technical 0.5%-60%, emulsifier 3%-20%, solvent 1%-30%, cosolvent 0%-5%, water to 100%;

[0106] The emulsifier is selected from anionic phosphates, such as Atplus 310;

[0107] The solvent is selected from one or more combinations of xylene, cyclohexanone, and dimethylformamide;

[0108] The cosolvent is selected from n-butanol or n-pentanol.

[0109] Mix the above substances evenly according to the formula ratio, stir until completely dissolved, add water and stir with a high-speed shear emulsifier until clear and transparent.

[0110] Main technical indicators of microemulsion: qualified transparent temperature range (0-50℃), persistent foaming of no more than 30 mL (after 1 minute), pH 4-8, and qualified 200-fold diluted emulsion stability, cold storage stability and hot storage stability measured according to GB / T 1603, GB / T 19136 and GB / T 19137.

Claims

1. A use of a carbazole compound as an agricultural fungicide, characterized in that: The structural formula of the carbazole compound is .

2. The use according to claim 1, characterized in that The content of the carbazole compound in the agricultural fungicide is 0.1 wt%-99 wt%.

3. The use according to claim 1, characterized in that The content of the carbazole compound in the agricultural fungicide is 1-80 wt%.

4. The use according to claim 1, characterized in that The content of the carbazole compound in the agricultural fungicide is 5-50 wt%.

5. The use according to claim 1, characterized in that The target of agricultural fungicides is Rhizoctonia solani ( Rhizoctonia solani ), Alternaria alternata ( Alternaria alternate ) or Pyricularia oryzae ( Pyricularia oryzae ).

6. The use according to claim 1, characterized in that The crops controlled by the agricultural fungicide are selected from tobacco or rice.

7. The use according to claim 1, characterized in that The agricultural fungicide is in the form of a suspension, a granule, a wettable powder, a water-dispersible granule, an emulsifiable concentrate, an aqueous emulsion or a microemulsion.

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