Chalcone compound and application thereof in prevention and treatment of plant pathogenic fungi

Abstract

The invention discloses a chalcone compound, and particularly discloses a structure of the compound. The invention also provides a preparation method and application thereof. A biological activity test result shows that the compound has relatively good inhibitory activity on six plant fungal diseases including lycium barbarum root rot bacteria, apple alternaria leaf spot bacteria, botrytis cinerea, celery leaf spot bacteria, valsa mali and potato black scurf bacteria, and the inhibitory activity of part of the compound on the bacteria is superior to that of azoxystrobin; the compound has a prospect of becoming a novel bactericide.

Description

Technical Field

[0001] This invention belongs to the field of agricultural chemistry, specifically involving the disclosure of a chalcone compound and its uses, particularly in the preparation of drugs for controlling root rot of wolfberry, leaf spot of apple, gray mold of tomato, leaf spot of celery, apple rot, and black scurf of potato. Background Technology

[0002] Antimicrobial agents derived from natural products have gained increasing attention in agricultural antimicrobial research due to their advantages such as being natural, low in toxicity, and easily degradable, exhibiting significant antimicrobial activity against crop pathogens. The long-term, large-scale use of traditional fungicides has led to the dual challenges of fungal resistance and environmental pollution caused by pesticide residues migrating through the soil-crop system. Therefore, there is an urgent need to develop greener, more environmentally friendly, and more efficient fungicides. Natural products, due to their structural diversity and significant biological activity, have become an important source for innovative drug development and are often used as templates for drug design.

[0003] Compared with traditional chemical pesticides, natural product-derived antimicrobial agents have many advantages. Their sources are widespread, with abundant plant resources providing rich raw materials for the development of agricultural antimicrobial agents. Plant-derived antimicrobial agents generally have low toxicity, are relatively safe for humans and animals, and are easily degraded in the environment, avoiding long-term environmental pollution. However, their production scale and stability need to be improved. In the research of natural product-derived agricultural antimicrobial agents, natural product derivatization is an important research direction. Derivatives obtained through structural modification show better efficacy in controlling pathogens and can serve as potential plant-derived fungicides.

[0004] In screening various natural products for their antifungal activity, the research group discovered that glycyrrhizin has certain inhibitory activity against plant pathogenic fungi. Subsequently, through structural derivatization, they obtained several natural product derivatives. Antibacterial activity tests revealed that some of these compounds had higher inhibitory activity than the commercially used azoxystrobin.

[0005] Based on this, the present invention designed and synthesized a series of Chalcogenide-like compounds. Through antibacterial activity tests, it was found that these compounds have significant inhibitory effects on Lycium barbarum root rot fungus, apple leaf spot fungus, tomato gray mold fungus, celery leaf spot fungus, apple rot fungus, and potato black scurf fungus, and can become novel candidate drugs against agricultural fungi. Summary of the Invention

[0006] The first objective of this invention is to provide a chalcone compound.

[0007] A second object of the present invention is to provide uses for the above-described compounds.

[0008] A chalcone compound having any of the following structural formulas:

[0009] The above-mentioned chalcone compounds are used in the preparation of drugs for the prevention or treatment of root rot of wolfberry, leaf spot of apple, gray mold of tomato, leaf spot of celery, apple rot and black scurf of potato.

[0010] Compared with existing commercially available chemical agents for controlling root rot of wolfberry, leaf spot of apple, gray mold of tomato, leaf spot of celery, apple rot, and black scurf of potato, the drug of the present invention has the following advantages:

[0011] (1) It has good bactericidal activity against Lycium barbarum root rot fungus, apple spot leaf drop fungus, tomato gray mold fungus, celery leaf spot fungus, apple rot fungus and potato black scurf fungus, and can be developed as a new bactericidal lead compound.

[0012] (2) The compound is a structural derivative of the natural product glycyrrhizin. Natural product structural derivative bactericides usually have low toxicity, are relatively healthy and safe for humans and animals, and are easily degraded in the environment, without causing long-term environmental pollution. Detailed Implementation

[0013] To better understand the present invention, the following detailed description of specific embodiments further illustrates the above-mentioned content of the present invention. However, this should not be construed as a limitation of the present invention.

[0014] The specific synthesis method of the chalcone compounds C1-C11 of the present invention is shown in the examples. The pure compounds were obtained by silica gel column chromatography and the chalcone compounds C1-C11 were identified by mass spectrometry and nuclear magnetic resonance.

[0015] Example 1: Synthesis of compound C1

[0016] The synthesis method of compound C1 described in this invention is carried out according to the following reaction formula:

[0017] The specific synthesis steps are as follows:

[0018] Synthesis of intermediate 1a: 2,4-Dihydroxybenzaldehyde (1.25 g, 9.0 mmol) and potassium carbonate (2.5 g, 18.0 mmol) were added sequentially to a 100 mL round-bottom flask, dissolved in acetone (30 mL). Isoprene bromide (1.55 mL, 13.5 mmol) was added dropwise with stirring at room temperature, and the mixture was heated to reflux for 8 h. The reaction solution gradually changed from an initial yellow paste to a white paste, with the solid being potassium carbonate. The reaction was monitored by TLC, and stopped after completion. The mixture was filtered using a sintered glass funnel and a circulating water pump to separate the solid and liquid. The clarified liquid was concentrated under reduced pressure, and the concentrate was purified by silica gel column chromatography using a mixture of PE:EA = 32:1 ~ PE:EA = 16:1 as the eluent, finally yielding a white solid 1a (1.4 g, 75%).

[0019] Synthesis of intermediate 2a: In a 100 mL round-bottom flask, compound 1a (1.4 g, 6.74 mmol) and potassium carbonate (1.87 g, 13.4 mmol) were dissolved in 25 mL of acetone. The mixture was stirred at room temperature for 10 min, and then dimethyl sulfate (1.28 mL, 10.05 mmol) was added dropwise. The mixture was heated under reflux for 8 h. The reaction was monitored by TLC. After the reaction was complete, the system was cooled to room temperature, and 5 mL of 25% ammonia was added to quench excess dimethyl sulfate. The system was a mixture of a clear liquid and a white paste-like solid. The white solid (unreacted potassium carbonate) was filtered off, and the liquid was poured into a separatory funnel and extracted three times with 25 mL of ethyl acetate. The organic phases were combined and then washed with saturated brine. The mixture was dried over anhydrous Na₂SO₄ and then concentrated under reduced pressure by filtration. The concentrate was purified by silica gel column chromatography with a mixture of PE:EA = 32:1 ~ PE:EA = 16:1 as the eluent, and finally a white solid 2a (1.2 g, 81%) was obtained.

[0020] Synthesis of intermediate 3a: 300 mg of 2a (300 mg, 1.36 mmol) was dissolved in 4 mL of ethanol to prepare solution 1; 2-acetylthiophenol was dissolved in 4 mL of ethanol, and then 2 mL of 20% wt% sodium hydroxide aqueous solution was added and stirred for 30 min to prepare solution 2; solution 1 was added dropwise to solution 2 in a 50 mL round-bottom flask and stirred continuously at 50 °C for 8 h. The reaction was monitored by TLC. After the reaction was complete, the pH of the reaction solution was adjusted to neutral, and the reaction solution was extracted three times with ethyl acetate. The collected organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (PE:EA = 16:1 ~ PE:EA = 8:1) to obtain 3a (yield 64%).

[0021] Synthesis of compound C1: 3a was placed in a 15 mL pressure-resistant tube, and a Claisen rearrangement reaction was carried out in 8 mL ethanol and 2 mL water at 135 °C. The reaction was monitored by TLC. After the reaction was complete, the reaction solution was cooled to room temperature and extracted three times with ethyl acetate. The collected organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (PE:EA = 8:1 ~ PE:EA = 4:1) to obtain C1.

[0022] Yield 70%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.07 – 7.99 (m, 3H), 7.54(d, J = 15.6 Hz, 2H), 7.01 – 6.95 (m, 2H), 6.46 (s, 1H), 6.16 (dd, J = 17.4, 10.7Hz, 1H), 5.00 – 4.94 (m, 2H), 3.94 – 3.84 (m, 9H), 1.46 (s, 6H). 13 C NMR (125MHz, Chloroform- d ) δ 189.8, 163.1, 161.4, 159.2, 147.9, 140.4, 131.9, 130.8,129.1, 128.8, 120.1, 115.7, 113.8, 110.2, 96.2, 55.8, 55.6, 55.4, 40.2, 27.5.HRMS (ESI) m / z [M+H] + Calcd for C 19 H 21 O3S329.12059, found 329.12011.

[0023] Example 2: Synthesis of compound C2

[0024] The experimental procedure was the same as in Example 1, except that 2-acetylpyrrole was used instead of 2-acetylthiophenol.

[0025] Yield 73%; 1 H NMR (500 MHz, DMSO- d 6) δ 11.87 (s, 1H), 10.07 (s, 1H), 7.85 (d, J= 15.7 Hz, 1H), 7.50 (s, 1H), 7.38 (d, J = 15.7 Hz, 1H), 7.17 (p, J =1.7 Hz, 1H), 7.11 – 7.09 (m, 1H), 6.52 (s, 1H), 6.28 – 6.22 (m, 2H), 4.94(dd, J = 14.0, 2.2 Hz, 2H), 3.83 (s, 3H), 1.45 (s, 6H). 13 C NMR (126 MHz, DMSO- d 6) δ 178.35, 159.45, 158.11, 147.56, 136.65, 133.23, 127.59, 126.50, 125.49,118.86, 116.13, 113.51, 110.04, 109.88, 99.97, 55.41, 26.98. HRMS (ESI) m / z[M+H] + Calcd for C 19 H 22 NO3312.15942, found 312.15841.

[0026] Example 3: Synthesis of compound C3

[0027] The experimental procedure was the same as in Example 1, except that 2-acetylfuran was used instead of 2-acetylthiophenol.

[0028] Yield 70%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.09 (d, J = 15.8 Hz, 1H), 7.63 (dd, J = 1.7, 0.7 Hz, 1H), 7.50 – 7.46 (m, 2H), 7.29 (dd, J = 3.5, 0.8 Hz, 1H), 6.56 (dd, J = 3.5, 1.7 Hz, 1H), 6.50 (s, 1H), 6.46 (s, 1H), 6.20 (dd, J=17.7, 10.5 Hz, 1H), 5.39 – 5.30 (m, 2H), 3.87 (s, 3H), 1.46 (s, 6H). 13 C NMR (125 MHz, Chloroform- d ) δ 179.1, 159.9, 158.7, 154.2, 147.9, 146.2, 140.7,129.1, 124.8, 119.4, 117.0, 116.3, 114.0, 112.4, 101.2, 55.7, 39.9, 27.2.HRMS(ESI) m / z [M+H] + Calcd for C 19 H 21 O4 313.14314, found 313.14246.

[0029] Example 4: Synthesis of compound C4

[0030] The experimental procedure was the same as in Example 1, except that acetylcyclohexane was used instead of 2-acetylthiophenol.

[0031] Yield 55%; 1 H NMR (500 MHz, Chloroform- d ) δ 7.84 (d, J = 16.1 Hz, 1H),7.42 (s, 1H), 6.78 (d, J = 16.1 Hz, 1H), 6.42 (d, J = 5.5 Hz, 2H), 6.18 (dd, J =17.7, 10.5 Hz, 1H), 5.39 – 5.27 (m, 2H), 3.84 (s, 3H), 2.72 (tt, J = 11.5, 3.4Hz, 1H), 1.93 – 1.62 (m, 6H), 1.43 (s, 6H). 13 C NMR (125 MHz, Chloroform- d) δ204.3, 159.3, 158.3, 147.9, 138.3, 127.7, 124.7, 123.3, 116.2, 114.1, 101.2,55.8, 48.8, 39.9, 29.2, 27.2, 26.1, 26.0.HRMS (ESI) m / z [M+H] + Calcd forC 21 H 29 O3329.21112, found 329.20993.

[0032] Example 5: Synthesis of compound C5

[0033] The experimental procedure was the same as in Example 1, except that p-bromoacetophenone was used instead of 2-acetylthiophene.

[0034] Yield 67%; 1 H NMR (500 MHz, Chloroform- d ) δ 7.99 (d, J = 15.7 Hz, 1H), 7.87 (d, J = 8.5 Hz, 2H), 7.63 (d, J = 8.5 Hz, 2H), 7.51 (d, J = 15.7 Hz, 1H), 7.47(s, 1H), 6.45 (s, 1H), 6.30 (s, 1H), 6.20 (dd, J = 17.8, 10.5 Hz, 1H), 5.46 –5.33 (m, 2H), 3.88 (s, 3H), 1.46 (s, 6H). 13 C NMR (126 MHz, Chloroform- d ) δ190.6, 159.9, 158.7, 147.9, 142.1, 137.8, 131.9, 130.2, 129.1, 127.4, 124.8,120.2, 116.5, 114.3, 55.8, 39.9, 27.2.HRMS (ESI) m / z [M+H] + Calcd forC 21 H 22 BrO3401.07468, found 401.07355.

[0035] Example 6: Synthesis of compound C6

[0036] The experimental procedure was the same as in Example 1, except that 2-acetylthiophene was replaced with p-fluoroacetophenone.

[0037] Yield 62%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.04 (dd, J = 8.8, 5.5 Hz, 2H), 8.00 (d, J = 15.7 Hz, 1H), 7.54 (d, J = 15.7 Hz, 1H), 7.48 (s, 1H), 7.26 (s,1H), 7.16 (t, J = 8.6 Hz, 2H), 6.46 (s, 1H), 6.31 (s, 1H), 6.20 (dd, J = 17.7,10.5 Hz, 1H), 5.45 – 5.32 (m, 2H), 3.88 (s, 3H), 1.46 (s, 6H). 13 C NMR (125MHz, Chloroform- d ) δ 190.0, 159.8, 158.6, 147.9, 141.8, 135.4, 131.2, 131.1,129.1, 124.7, 120.2, 116.5, 115.8, 115.6, 114.3, 101.3, 55.8, 39.9, 27.2.HRMS (ESI) m / z [M+H] + Calcd for C 21 H 22 FO3341.15475, found 341.15360.

[0038] Example 7: Synthesis of compound C7

[0039] The experimental procedure was the same as in Example 1, except that p-dimethylaminoacetophenone was used instead of 2-acetylthiophene.

[0040] Yield 74%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.01 (d, J= 9.0 Hz, 2H), 7.98 (d, J = 15.8 Hz, 1H), 7.63 (d, J = 15.7 Hz, 1H), 7.48 (s, 1H), 6.71 (d, J =9.0 Hz, 2H), 6.46 (s, 1H), 6.34 (s, 1H), 6.21 (dd, J = 17.7, 10.5 Hz, 1H), 5.44– 5.29 (m, 2H), 3.87 (s, 3H), 3.07 (s, 6H), 1.46 (s, 6H). 13 C NMR (125 MHz, Chloroform- d ) δ 189.0, 159.5, 157.9, 153.3, 148.1, 139.3, 130.9, 128.6,126.8, 124.5, 120.8, 117.1, 113.9, 110.9, 101.2, 55.7, 40.2, 39.9, 27.2.HRMS(ESI) m / z [M+H] + Calcd for C 23 H 28 NO3366.20637, found 366.20590.

[0041] Example 8: Synthesis of compound C8

[0042] The experimental procedure was the same as in Example 1, except that 2-acetylthiasol was replaced with p-tert-butylacetophenone.

[0043] Yield 50%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.01 (d, J = 15.8 Hz, 1H), 7.97 (d, J = 8.5 Hz, 2H), 7.59 (d, J = 15.8 Hz, 1H), 7.51 (d, J = 8.5 Hz, 2H), 7.49(s, 1H), 6.46 (s, 1H), 6.34 (s, 1H), 6.20 (dd, J= 17.7, 10.5 Hz, 1H), 5.42 –5.31 (m, 2H), 3.87 (s, 3H), 1.46 (s, 6H), 1.36 (s, 9H). 13 C NMR (125 MHz, Chloroform- d ) δ 191.2, 159.7, 158.4, 156.1, 147.9, 141.0, 136.4, 128.9,128.6, 125.6, 124.7, 120.7, 116.7, 114.1, 101.3, 55.8, 39.9, 35.2, 31.3,27.2. HRMS (ESI) m / z [M+H] + Calcd for C 25 H 31 O3379.22677, found 379.22569.

[0044] Example 9: Synthesis of compound C9

[0045] The experimental procedure was the same as in Example 1, except that p-isobutylacetophenone was used instead of 2-acetylthiasol.

[0046] Yield 48%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.01 (d, J = 15.7 Hz, 1H), 7.94 (d, J = 8.3 Hz, 2H), 7.58 (d, J = 15.7 Hz, 1H), 7.49 (s, 1H), 7.26 (d, J = 8.3Hz, 2H), 6.46 (s, 1H), 6.32 (s, 1H), 6.20 (dd, J = 17.7, 10.5 Hz, 1H), 5.43 –5.29 (m, 2H), 3.87 (s, 3H), 2.55 (d, J = 7.2 Hz, 2H), 1.46 (s, 6H), 0.93 (d, J =6.6 Hz, 6H). 13 C NMR (126 MHz, Chloroform- d) δ 191.2, 159.7, 158.4, 147.9,146.9, 141.0, 136.7, 129.4, 128.9, 128.6, 124.7, 120.7, 116.7, 114.1, 101.3,55.8, 45.6, 39.9, 30.3, 27.2, 22.5.HRMS (ESI) m / z [M+H] + Calcd for C 25 H 31 O3379.22677, found 379.22556.

[0047] Example 10: Synthesis of compound C10

[0048] The experimental procedure was the same as in Example 1, except that 2-acetylthiophene was replaced with p-propylacetophenone.

[0049] Yield 72%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.01 (d, J = 15.8 Hz, 0H), 7.94 (d, J = 8.2 Hz, 1H), 7.58 (d, J = 15.7 Hz, 0H), 7.49 (s, 0H), 7.29 (d, J = 8.2Hz, 1H), 6.45 (d, J = 7.6 Hz, 1H), 6.20 (dd, J = 17.7, 10.5 Hz, 0H), 5.40 – 5.30(m, 1H), 3.86 (s, 1H), 2.66 (dd, J = 8.5, 6.8 Hz, 1H), 1.73 – 1.62 (m, 1H), 1.46 (s, 3H), 0.96 (t, J = 7.3 Hz, 1H). 13 C NMR (126 MHz, Chloroform- d) δ 191.3,159.7, 158.4, 147.9, 147.8, 141.1, 136.7, 128.9, 128.7, 128.7, 124.8, 120.6,116.6, 113.9, 101.2, 55.7, 39.9, 38.2, 27.2, 24.4, 13.9.HRMS (ESI) m / z [M+H] + Calcd for C 24 H 29 O3365.21112, found 365.20965.

[0050] Example 11: Synthesis of compound C11

[0051] The experimental procedure was the same as in Example 1, except that 2-acetylthiophene was replaced with p-ethoxyacetophenone.

[0052] Yield 69%; 1 H NMR (500 MHz, Chloroform- d ) δ 8.04 – 7.97 (m, 3H), 7.58(d, J = 15.7 Hz, 1H), 7.48 (s, 1H), 6.96 (d, J = 8.9 Hz, 2H), 6.46 (s, 1H), 6.20(dd, J = 17.7, 10.5 Hz, 1H), 5.44 – 5.28 (m, 2H), 4.11 (q, J = 7.0 Hz, 2H), 3.86(d, J = 0.8 Hz, 3H), 1.46 (s, 6H), 1.45 – 1.41 (m, 4H). 13 C NMR (125 MHz, Chloroform- d ) δ 189.9, 162.6, 159.6, 158.3, 147.9, 140.7, 131.7, 130.9,128.8, 124.7, 120.4, 116.7, 114.3, 114.0, 101.2, 63.8, 55.7, 39.9, 27.2,14.8. HRMS (ESI) m / z [M+H] + Calcd for C 23 H27 O4367.19039, found 367.18991.

[0053] Example 12: In vitro antifungal activity test and results of compounds C1-C11

[0054] First, an in vitro antifungal activity screening was conducted. The concentrations of C1-C11 compounds were determined using the mycelial growth rate method, with 50 μg / mL as the initial screening concentration. The antifungal activity of each compound was assessed using *Fusariumacuminatum* (root rot of Codonopsis pilosula), *Fusarium tricinctum* (root rot of Lycium barbarum), *Fusarium solani* (root rot of Onion), *Alternaria mali* (root rot of Apple), *Botrytis cinerea* (root rot of Eggplant), *Deuteromycetes* (root rot of Celery), *Botryosphaeria dothidea* (root rot of Apple), *Fusarium solani* (root rot of Eggplant), and *Rhizoctonia solani* (root rot of Potato). The commercially available azoxystrobin was selected as a positive control. All experiments were performed in triplicate. The specific operational steps are as follows:

[0055] 1) Activation of the strain: Inoculate the frozen strain onto PDA solid medium on a clean bench, label it, and incubate it in a 25°C incubator for 3 to 5 days. After three generations of activation, proceed with subsequent experiments.

[0056] 2) Sterilization: Sterilize the PDA culture medium at 121℃ for 30 min in a steam sterilizer. Sterilize the sterile culture dishes, pipettes, and alcohol lamps under UV light in a laminar flow hood for 30 min.

[0057] 3) Preparation of drug-containing PDA medium: Weigh 10 mg of the target compound and dissolve it in 1 mL of dimethyl sulfoxide (DMSO) to prepare a drug solution with a concentration of 10 mg / mL. Mix the drug solution with the PDA medium until it reaches a concentration of 50 °C. m The test concentration was calculated as g / mL, and while still hot, it was poured into a petri dish with a diameter of 85 mm. The dish was then labeled and placed horizontally to cool until solidified.

[0058] 4) Inoculation: Place a 5 mm diameter punch and inoculation needle in the outer flame of an alcohol lamp and burn them. Then, make a sufficient amount of mycelium cake on the mycelium tray, pick up the mycelium cake with the needle and inoculate it into the PDA medium. Seal the edge of the culture dish with sealing film. After 24 hours, invert the plate and incubate it in a constant temperature incubator for 3 to 7 days.

[0059] 5) Measurement: When the hyphae of the blank control completely covered the culture dish, the colony diameter was measured using the cross-sectional method, and the final diameter was taken as the average value. The formula for calculating the antibacterial rate (Y) of the compound is as follows:

[0060] Where D0 represents the mean diameter of colonies in the blank group, Dt represents the mean diameter of colonies grown on drug-based PDA, and J represents the diameter of the bacterial pellet.

[0061] The results are shown in Table 1.

[0062] Table 1. Compounds C1-C11 at 50°C m In vitro antifungal activity at g / mL

[0063] As shown in Table 1, the chalcone compounds C1-C11 prepared in this invention exhibit certain inhibitory activities against Lycium barbarum root rot fungus, Apple leaf spot fungus, Tomato gray mold fungus, Celery leaf spot fungus, Apple rot fungus, and Potato black scurf fungus. Among them, compounds C2 and C3 have very good inhibitory activity against Potato black scurf fungus, and compounds C1-C6 have good inhibitory activity against Apple rot fungus. All of these are superior to the commercially available positive control agent pyraclostrobin. Therefore, the compounds of this invention have the potential to be used in the preparation of pesticides, especially agricultural antifungal agents.

[0064] In summary, the chalcone compounds of this invention have simple structures and convenient synthetic routes. Some compounds have shown significant inhibitory activity against six pathogens, especially apple rot fungus and potato black scurf fungus, and are worthy of further research. They are expected to be developed into novel plant-derived pesticides.

Claims

1. This invention relates to a chalcone compound and its use, specifically the application of this compound in the control of Lycium barbarum root rot fungus, Apple leaf spot fungus, Tomato gray mold fungus, Celery leaf spot fungus, Apple rot fungus, and Potato black scurf fungus.

2. A chalcone compound according to claim 1, characterized in that, The compound has any of the following structural formulas:

3. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for preventing or treating root rot of Lycium barbarum.

4. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for the prevention or treatment of apple spot leaf spot pathogens.

5. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for the prevention or treatment of tomato gray mold.

6. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for preventing or treating celery leaf spot disease.

7. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for preventing or resisting apple rot fungi.

8. The use of the chalcone compounds C1-C11 according to claim 2 in the preparation of drugs for the prevention or treatment of potato black scurf.

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