CN116082313A - Compound for preventing and treating plant fungal diseases and preparation method thereof - Google Patents

Abstract

The invention discloses a compound with a structure shown as a formula (I), which is obtained by splicing and structurally modifying tryptamine or derivatives thereof and fluxapyroxad. The invention improves the inhibition activity of the compound on plant fungal diseases and is beneficial to further derivatization and diversification of the structure of the compound so as to overcome drug resistance. The chemical raw materials required for synthesizing the compound are cheap and easy to obtain, the synthesis steps are relatively simple, and the method has the advantages of low input cost, short research and development period and the like.

Description

Compound for preventing and treating plant fungal diseases and preparation method thereof

Technical Field

The invention relates to a compound for preventing and treating plant fungal diseases and a preparation method thereof, belonging to the fields of pesticides and chemistry.

Background

Succinate Dehydrogenase (SDH) inhibitors inhibit mitochondrial function by acting on complex II on the respiratory electron transfer chain of pathogenic bacteria (also known as succinate dehydrogenase or ubiquinone succinate reductase) to interfere with succinate dehydrogenase on the respiratory electron transfer chain, prevent it from generating energy, inhibit pathogenic bacteria from growing, and ultimately lead to their death, for the purpose of controlling diseases, for example 3- (difluoromethyl) -1-methyl-N- [2- (3, 4, 5-trifluorophenyl) phenyl ] -1H-pyrazole-4-carboxamide (commonly known as fluxapyroxad) can be used for controlling a variety of plant pathogenic fungi. SDH inhibitors have become the most promising class of bactericides in recent years due to their high efficacy, broad spectrum bactericidal activity and relatively low risk of resistance.

Fluoxapyroxad

Tryptamine (Tryptamine), known under the chemical name 3- (2-aminoethyl) indole, a series of derivatives of Tryptamine, which, due to its structural particularity, possess tremendous physiological and pharmacological properties in the central nervous system, can form the backbone of many pharmaceutical compounds, such as the hallucinogen lysergic acid diethylamine (LSD), the antimalarial agent spiroindolone (Yeung et al, 2010,J Med Chem.53:5155-5164), the hyperalgesic spirocyclohexane derivative, and the farnesyl ester X receptor antagonist azepinoindole (azepinndole) derivative. The prior literature reports the application of the derivatives in anti-migraine medicines such as sumatriptan, li Zapu and the like on the market, and the derivatives can also be used for synthesizing indole alkaloids such as vincamine, vinpocetine and the like.

Derivatives based on tryptamine structures, such as 5-hydroxytryptamine, can be used as a signaling molecule in plants to regulate plant growth, development and response to biotic and abiotic stresses by modulating the level of reactive oxygen species in the plant. It was found that 5-hydroxytryptamine can regulate the development of Arabidopsis root systems by altering the level of reactive oxygen species and jasmonate ethylene signaling. Under salt stress, 5-hydroxytryptamine can increase the salt tolerance of canola by reducing the content of hydrogen peroxide and malondialdehyde.

Derivatives based on tryptamine structures such as melatonin (N-acetyl-5-methoxyryptamine) can be used as health products for regulating human sleep, retina physiology, enhancing immunity, resisting aging and the like, are relatively mature in research and application in human beings, and have been commercialized at present. Also participate in important physiological processes such as growth regulation, adversity stress, biological stress and the like in plants. Studies have shown that melatonin not only has an inhibitory effect on a part of bacterial diseases and viral diseases, such as Rice bacterial leaf blight caused by gram-negative bacteria xanthomonas (Xanthomonas oryzae) and Rice dwarf caused by Rice dwarf virus (Rice dwarf virus). Melatonin also has an inhibitory effect on plant pathogenic fungi (CN 114680114 a).

Tryptamine is a compound skeleton of a plurality of important medicines, derivatives based on a tryptamine structure such as 5-hydroxytryptamine, melatonin and the like are also involved in important physiological processes such as plant growth and development, adversity stress and the like, and regarding the application of tryptamine and series derivatives to agricultural chemicals, only a part of literature reports are used for preventing and treating part of bacterial diseases and viral diseases, and application rare literature reports are reported aiming at the prevention and treatment of plant pathogenic fungi of common economic crops. According to the invention, tryptamine and fluxapyroxad are spliced and different chemical groups are selected for modification, so that the prevention and treatment effects of the compound on plant pathogenic fungi are systematically researched, and the compound is expected to become a potential antibacterial molecule.

Tryptamine and derivatives thereof

Disclosure of Invention

The first object of the invention is to provide a compound which is obtained by splicing and structurally modifying tryptamine or a derivative thereof and fluxapyroxad, wherein the structural formula of the compound is shown in the following formula (I):

wherein R is ¹ Is trifluoromethyl or difluoromethyl; r is R ² Is a conventional substituent on the benzene ring, and R ² At any substituted position on the benzene ring, mono-or poly-substituted.

Preferably, R ² Is hydrogen, hydroxy, halogen, alkyl, alkoxy, trifluoroalkyl, phenyl.

Further preferably, R ¹ Is trifluoromethyl; r is R ² 5,6-Cl.

The second object of the present invention is to provide a method for synthesizing a compound of formula (I), which comprises the following steps:

in the above synthetic route, R in formula II, formula III, formula IV, formula V ² The substituents are all the same as R in the formula (I) ² Substituents are defined identically; r in formula VI, formula VII ¹ Substituents, all of which are identical to R in the formula (I) ¹ Substituents are as defined above.

The specific synthesis steps are as follows:

(1) Adding N, N-dimethylformamide into a round bottom flask, slowly dropwise adding phosphorus oxychloride under ice bath condition, continuing to react for 0.5 hour at the temperature of 0 ℃ after the dropwise adding is finished, dissolving the raw material II into the N, N-dimethylformamide, slowly dropwise adding into the reaction solution, continuing to react for 2 hours at the temperature of 0 ℃, and monitoring the reaction by TLC until the reaction is complete; adding water into a reaction system to quench the reaction under ice bath condition after the reaction is completed, regulating the pH to 9 by 2M NaOH, extracting by ethyl acetate, combining organic phases, drying and concentrating to obtain a compound of a formula III;

(2) At N ₂ Placing the compound III, ammonium acetate and nitromethane in a three-mouth bottle under the protection of atmosphere, reacting at 50 ℃ for 3-5 hours until the reaction is complete, removing unreacted nitromethane by rotary evaporation under reduced pressure after the reaction is complete, washing solid residues with water, and drying in vacuum to obtain the compound of formula IV;

(3) At N ₂ Adding lithium aluminum hydride into tetrahydrofuran solution containing compound IV slowly under the conditions of atmosphere protection and ice bath, then heating slowly to room temperature, adding water quenching unreacted lithium aluminum hydride under the conditions of ice bath after TLC monitoring reaction is completed, adding saturated sodium tartrate solution, andadding methyl tertiary butyl ether for extraction and liquid separation, merging organic phases, drying under reduced pressure, concentrating to obtain an intermediate V, and purifying a crude product of the intermediate V by column chromatography;

(4) At N ₂ Under the atmosphere protection condition, dissolving a compound VI in anhydrous dichloromethane, dropwise adding 2-3 drops of anhydrous N, N-dimethylformamide, slowly dropwise adding oxalyl chloride solution under ice bath, after the dropwise adding is finished, recovering the reaction to room temperature for reaction for 6-8 hours, removing dichloromethane and unreacted oxalyl chloride by rotary evaporation under reduced pressure, and adding anhydrous dichloromethane again to prepare an acyl chloride solution for later use;

(5) At N ₂ Under the atmosphere protection condition, dissolving the intermediate V in anhydrous dichloromethane, dropwise adding a proper amount of triethylamine, slowly dropwise adding the acyl chloride solution obtained in the step (4) into the solution under the ice bath condition, monitoring the reaction to be complete by TLC, adding water for quenching reaction, extracting with dichloromethane, drying and concentrating, and separating and purifying the final product of the compound formula (I) by column chromatography.

The compound provided by the invention can be used for preventing and controlling plant fungal diseases, wherein the plant fungal diseases comprise fusarium graminearum (Fusarium graminearum), botrytis cinerea (Botrytis cinerea), sclerotinia sclerotiorum (Sclerotinia sclerotiorum), hirsutella pseudodiscus (Pestalotiopsis), brown rot of peach (Monilinia fructicola), small spot of corn (Bipolaris maydis), rhizoctonia solani (Rhizoctonia solani) and alternaria alternata (Altermaria alternata).

Compared with the prior art, the invention has the following advantages:

according to the invention, through structural splicing and modification of the two known compounds, the inhibition activity of the compounds on plant fungal diseases is improved, and the synthesized compounds have more modification sites, so that the further derivatization and diversification of the structures of the compounds are facilitated, and the drug resistance is overcome. The compound can be used alone or in combination with other chemical pesticides, and can greatly improve pesticide effect and reduce pesticide application amount. The chemical raw materials required for synthesizing the compound are cheap and easy to obtain, the synthesis steps are relatively simple, and partial tryptamine derivative intermediates are commercial products, so that the input cost can be reduced, and the research and development period can be shortened.

Drawings

FIG. 1 is a nuclear magnetic resonance spectrum (hydrogen spectrum) of Compound I-025.

FIG. 2 is a nuclear magnetic resonance spectrum (carbon spectrum) of Compound I-025.

FIG. 3 is a nuclear magnetic resonance spectrum (fluorine spectrum) of Compound I-025.

FIG. 4 is a graph showing the inhibition effect of compound I-025 on fungal diseases of 8 common cash crops at a concentration of 200. Mu.M.

FIG. 5 is a graph showing the inhibitory effect of Compound I-025 on 3 fungal diseases of Botrytis cinerea, sclerotinia sclerotiorum and Rhizoctonia solani at concentrations of 100. Mu.M, 50. Mu.M, 25. Mu.M, 12.5. Mu.M, 6.25. Mu.M and 3.125. Mu.M.

FIG. 6 is a graph showing the inhibitory effect of Compound I-025 on infection of rape leaves by Sclerotinia sclerotiorum at a concentration of 100. Mu.M and 400. Mu.M.

FIG. 7 is a graph showing the inhibitory effect of Compound I-025 on the infestation of tomato fruits by Botrytis cinerea at concentrations of 100. Mu.M, 200. Mu.M, 400. Mu.M.

Detailed Description

The present invention will be described in detail by way of specific examples. Those skilled in the art will appreciate that the following embodiments and examples are illustrative of the present invention only and should not be construed as limiting the scope of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention. In the examples, unless otherwise indicated, all relevant reagents were commercially available and all methods used were conventional in the art. The non-specific conditions are performed according to conventional conditions or conditions suggested by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.

Example 1: synthesis of Compound I-025

(1) Synthesis of intermediate (5, 6-dichloro-1H-indol-3-yl) ethylamine:

step a: III-025 intermediate 5, 6-dichloroindole-3-formaldehyde synthesis: at N ₂ 50mL of anhydrous N, N-dimethylformamide was added to a 250mL three-necked flask under the protection of atmosphere, phosphorus oxychloride (2.5 mL,25.6 mmol) was added dropwise to the system under the ice bath condition, the reaction was carried out for 30 minutes at 0℃after the addition was completed, commercially available 5, 6-dichloroindole (1.86 g,10 mmol) was dissolved in 10mL of anhydrous N, N-dimethylformamide, and the reaction was continued by dropping the above reaction solution at 0℃for 2 hours. After TLC monitored complete reaction of the starting materials, water was added to the system to quench unreacted complete phosphorus oxychloride, extracted with ethyl acetate (3 x 30 ml), the organic phases combined and dried over anhydrous sodium sulfate, concentrated under reduced pressure to afford intermediate iii-025 as a pale yellow solid, yield: 95%.

Step b: synthesis of IV-025 intermediate: at N ₂ In a three-necked flask, intermediate III-025 (2.14 g,10 mmol) and ammonium acetate (2.31 g,30 mmol) were added under atmosphere protection, followed by 30mL nitromethane, heated to 50deg.C for 5 hours, after TLC monitored complete reaction of the starting materials, unreacted nitromethane was removed under reduced pressure, the remaining solid residue was washed with water, and dried under vacuum to afford intermediate IV-025 as a yellow solid, yield: 98%.

Step c: synthesis of v-025 intermediate: at N ₂ A tetrahydrofuran solution of intermediate IV-025 (2.56 g,10 mmol) was added dropwise under ice bath conditions under atmosphere protection, and the mixture was allowed to react overnight at room temperature after completion of the dropwise addition. After completion of the reaction, TLC was followed by adding 10mL of H to the system under ice bath ₂ O to quench excess lithium aluminum hydride, add saturated sodium potassium tartrate solution to the mixture and stir for 30 min, add methyl t-butyl ether to extract (3 x 30 ml), combine the organic phases and dry over anhydrous sodium sulfate, concentrate under reduced pressure to give the crude intermediate 5, 6-dichloro-1H-indol-3-yl) ethylamine in yield: 87%.

(2) Synthesis of Compound I-025:

step d: synthesis of vii-025 intermediates: at N ₂ Under the protection of atmosphere, adding a commercial raw material 3- (trifluoromethyl) -1-methyl-1H-pyrazole-4-carboxylic acid (1.9 g,10 mmol) into a round-bottomed flask, adding 60mL of anhydrous dichloromethane, dropwise adding 2-3 drops of anhydrous N, N-dimethylformamide, slowly dropwise adding oxalyl chloride (1 mL,12 mmol) under the ice bath condition, recovering to room temperature for reaction for 6-8 hours after the dropwise adding is finished, removing solvent dichloromethane and unreacted oxalyl chloride by reduced pressure rotary evaporation, and adding anhydrous dichloromethane again to prepare an acyl chloride solution of VII-025 for later use.

Step e: synthesis of I-025: at N ₂ Under the protection of atmosphere, dissolving intermediate V-025 (2 mmol,0.46 g) synthesized in the step c in 10mL of anhydrous dichloromethane, adding anhydrous triethylamine (3 mmol,0.46 mL), slowly dropwise adding the acid chloride solution (2.4 mmol,1.2 eq.) of VII-025 obtained in the step d into the reaction liquid under the ice bath condition, monitoring the TLC until the reaction is complete, adding water to quench the reaction, extracting the dichloromethane, washing with saturated salt water, retaining an organic phase, adding anhydrous sodium sulfate for drying, concentrating to obtain a crude product, and separating by rapid column chromatography (DCM/PE=2/1) to obtain a final product I-025 gray solid, namely 0.69g, and the yield: 85%.

N-(2-(5,6-dichloro-1H-indol-3-yl)ethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-car boxamide:

¹ H NMR(600MHz,Chloroform-d)δ8.27(s,1H),7.86(s,1H),7.66(s,1H),7.46(s,1H),7.07(s,1H),6.07(s,1H),3.93(s,3H),3.71(q,J＝6.5Hz,3H),2.99(t,J＝6.8Hz,2H).

¹³ C NMR(150MHz,Chloroform-d)δ160.69,135.38(d,J＝41.2Hz),128.53–122.38(m),119.89,112.76(d,J＝39.3Hz),40.04(d,J＝33.3Hz),25.05.

¹⁹ F NMR(565MHz,Chloroform-d)δ-59.81.

The specific nuclear magnetic resonance spectrum is shown in figures 1-3.

The synthesis process of one specific compound of the invention is shown above, and other series of compounds can be synthesized by the same synthesis route and principle, and the following table 1 is part of the compounds synthesized by the invention

TABLE 1 specific Compound classes and substituents

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EXAMPLE 2 determination of the inhibitory Activity of Compounds I-025 against 8 plant disease pathogenic fungi

Test one, determination of the inhibition of eight pathogenic fungi by Compounds

(1) Cultivation of phytopathogenic fungi: inoculating pathogenic fungi on PDA culture medium, culturing in constant temperature incubator at 25+ -0.1deg.C for 3-6 days, and growing mycelium.

(2) The in vitro inhibition activity was determined by hypha growth rate method: test compounds and control agents were formulated with DMSO (dimethyl sulfoxide) to 20mM solutions, and then calculated amounts of the solutions were formulated with PDA medium to test concentrations. DMSO is used as a blank control, and boscalid and fluxapyroxad are used as positive controls. The medium was prepared as a plate in 9cm dishes, three replicates per treatment, inoculated with 5mm cakes and placed in a thermostated incubator at 25.+ -. 0.1 ℃. After the colony diameter in the blank control culture dish is about 6-9cm, the colony diameter of each treatment and control is measured by a crisscross method.

Calculating the bacteriostasis rate: colony growth diameter (mm) =colony measurement diameter (mm) -cake diameter (mm);

hypha growth inhibition (%) = [ colony growth diameter of blank control (mm) -colony growth diameter of drug-containing medium (mm) ]/colony growth diameter of blank control (mm) ×100%.

Wherein, rhizoctonia solani (Rhizoctonia solani): preparing a PDA solid culture medium, adding a succinic dehydrogenase derivative containing a tryptamine structure into the culture medium to ensure that the final concentration is 200 mu M, scraping hypha on a 5mm rhizoctonia solani block, placing the hypha in the middle of the culture medium, placing the hypha at room temperature for culturing for 2-3 days, and calculating the bacteriostasis rate, wherein each group is repeated for 3 times.

Fusarium graminearum (Fusarium graminearum), botrytis cinerea, sclerotinia sclerotiorum (Sclerotinia sclerotiorum), mucor pseudodiscus (Pestalotiopsis), monilinia fructicola (Monilinia fructicola), alternaria farina (Bipolaris maydis), alternaria alternifolia (Altermaria alternata) and other 7 plant pathogenic bacteria testing methods are the same as those of Rhizoctonia solani (Rhizoctonia solani), except that the culture time of different strains is not equal for 3-7 days.

The results of the bacteriostasis rate of the compound I-025 and the positive control on the pathogenic fungi of 8 plant diseases are shown in table 1, and the bacteriostasis effect of the compound I-025 is shown in figure 4. As can be seen from the results in Table 1, the bacteriostatic activity of compound I-025 is generally higher than that of fluxapyroxad or melatonin.

Table 1 bacteriostasis rate of three compounds against 8 plant disease pathogenic fungi

The potato dextrose agar medium PDA medium formulation referred to in this example: selecting fresh potato, cleaning, peeling, weighing 200g, cutting into small pieces, adding water, boiling for 20-30 min, tearing by a glass rod, filtering with four layers of gauze, adding 20g D-glucose, stirring, cooling slightly, supplementing water to 1000mL, adding 15g of Agar, and autoclaving at 115 deg.C for 20min.

And (2) testing II: half inhibition concentration determination of Compound I-025 against 3 fungal diseases

The inhibitory activity of the inhibitor compound I-025 against 3 fungal diseases of Botrytis cinerea, sclerotinia sclerotiorum (Sclerotinia sclerotiorum) and Rhizoctonia solani (Rhizoctonia solani) was measured in the same manner as in the test method of example 3, except that the test compound I-025 liquid medicine and the PDA medium were formulated into test concentrations of 100. Mu.M, 50. Mu.M, 25. Mu.M, 12.5. Mu.M, 6.25. Mu.M and 3.125. Mu.M. The inhibition rate was calculated to give half inhibition concentrations of Compound I-025 to Botrytis cinerea, sclerotinia sclerotiorum and Rhizoctonia solani of 44.50.+ -. 0.41. Mu.M, 19.75.+ -. 0.41. Mu.M and 49.70.+ -. 0.53. Mu.M, respectively. The antibacterial effect is shown in figure 5.

And (3) test III: determination of inhibition effect of compound I-025 on sclerotinia sclerotiorum fungal disease infected rape leaves

Cleaning and sterilizing fresh picked rape leaves, dripping compound I-025 solution with concentration of 100 μm and 400 μm in the middle of the leaves, treating at room temperature for 6-8 hr, inoculating sclerotinia sclerotiorum (Sclerotinia sclerotiorum) bacterial cake with size of 8mm in the center of the leaves by using a puncher, culturing in a constant temperature incubator with temperature of 25+ -0.1deg.C for 2-3 days, and observing the size of bacterial plaque of sclerotinia sclerotiorum infected with rape leaves, and the result is shown in figure 6. As can be seen from the figure, the area of plaque on the leaf at the drop I-025 was significantly reduced, and there was substantially no plaque on the leaf at a compound concentration of 400. Mu.M.

And (3) testing four: determination of inhibition effect of compound I-025 on botrytis cinerea fungal disease infection of tomato fruits

Fresh and uniformly sized tomato fruits are purchased in a supermarket, cleaned, disinfected and dried, uniformly sized cross-shaped wounds are marked on the surface of the tomato by using a disinfected blade, inhibitor compound I-025 is dripped into spore suspension of botrytis cinerea to prepare 100 mu M, 200 mu M and 400 mu M concentration of spore suspension with medicine, the spore suspension with medicine is dripped into the cross-shaped wounds on the surface of the tomato, the cross-shaped wounds are cultured in a constant temperature incubator at 25+/-0.1 ℃ for 2-3 days, and the bacterial plaque size of the botrytis cinerea infected on the surface of the tomato is observed, and the result is shown in figure 7. From the figure, the compound I-025 can inhibit the infection of the tomato fruits by the botrytis cinerea and has an quantitative effect relationship.

In conclusion, the compound prepared by the invention has inhibitory activity on various plant pathogenic fungi in vivo and in vitro, can be used for preparing novel bactericides, and has important significance in improving disease control effect. In addition, the tryptamine structure in the compound has more modification sites, which is favorable for further derivatization and diversification of the structure of the compound and is favorable for overcoming drug resistance.

Claims (7)

1. A compound of the formula (i):

wherein R is ¹ Is trifluoromethyl or difluoromethyl; r is R ² Is a conventional substituent on the benzene ring, and R ² At any substituted position on the benzene ring, mono-or poly-substituted.

2. A compound according to claim 1, wherein: r is R ² Is hydrogen, hydroxy, halogen, alkyl, alkoxy, trifluoroalkyl, phenyl.

3. A compound according to claim 1, wherein: r is R ¹ Is trifluoromethyl; r is R ² 5,6-Cl.

4. A method of synthesizing a compound according to any one of claims 1 to 3, comprising the steps of:

(1) Adding N, N-dimethylformamide into a round bottom flask, slowly dropwise adding phosphorus oxychloride under ice bath condition, continuing to react for 0.5 hour at the temperature of 0 ℃ after the dropwise adding is finished, dissolving the raw material II into the N, N-dimethylformamide, slowly dropwise adding into the reaction solution, continuing to react for 2 hours at the temperature of 0 ℃, and monitoring the reaction by TLC until the reaction is complete; adding water into a reaction system to quench the reaction under ice bath condition after the reaction is completed, regulating the pH to 9 by 2M NaOH, extracting by ethyl acetate, combining organic phases, drying and concentrating to obtain a compound of a formula III;

(2) At N ₂ Placing the compound III, ammonium acetate and nitromethane in a three-mouth bottle under the protection of atmosphere, reacting at 50 ℃ for 3-5 hours until the reaction is complete, removing unreacted nitromethane by rotary evaporation under reduced pressure after the reaction is complete, washing solid residues with water, and drying in vacuum to obtain the compound of formula IV;

(3) At N ₂ Atmosphere protection, ice bath conditionsSlowly adding lithium aluminum hydride into tetrahydrofuran solution containing a compound IV, then slowly heating to room temperature, adding water to quench unreacted lithium aluminum hydride under the ice bath condition after TLC monitoring reaction is completed, adding saturated sodium tartrate solution, adding methyl tertiary butyl ether to extract and separate liquid, combining organic phases, drying under reduced pressure, concentrating to obtain an intermediate V, and purifying a crude product of the intermediate V by column chromatography;

(4) At N ₂ Under the atmosphere protection condition, dissolving a compound VI in anhydrous dichloromethane, dropwise adding 2-3 drops of anhydrous N, N-dimethylformamide, slowly dropwise adding oxalyl chloride solution under ice bath, after the dropwise adding is finished, recovering the reaction to room temperature for reaction for 6-8 hours, removing dichloromethane and unreacted oxalyl chloride by rotary evaporation under reduced pressure, and adding anhydrous dichloromethane again to prepare an acyl chloride solution for later use;

(5) At N ₂ Under the atmosphere protection condition, dissolving the intermediate V in anhydrous dichloromethane, dropwise adding a proper amount of triethylamine, slowly dropwise adding the acyl chloride solution obtained in the step (4) into the solution under the ice bath condition, monitoring the reaction to be complete by TLC, adding water for quenching reaction, extracting with dichloromethane, drying and concentrating, and separating and purifying the final product of the compound formula (I) by column chromatography.

5. Use of a compound according to any one of claims 1 to 3 for controlling plant fungal diseases.

6. The use according to claim 5, wherein: the plant fungal diseases are Fusarium graminearum (Fusarium graminearum), botrytis cinerea, sclerotinia sclerotiorum (Sclerotinia sclerotiorum), mucor pseudodiscus (Pestalotiopsis), monilinia fructicola (Monilinia fructicola), alternaria corn (Bipolaris maydis), rhizoctonia solani (Rhizoctonia solani) and Alternaria alternifolia (Altermaria alternata).

7. A fungicide for controlling plant fungal diseases, which comprises the compound according to any one of claims 1 to 3 in an active ingredient.

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