Novel methoxyimino acetate derivative containing chloroacetamide structure as well as preparation method and application of novel methoxyimino acetate derivative

Abstract

The invention discloses a novel methoxyimino acetate derivative containing a chloroacetamide structure as well as a preparation method and application of the novel methoxyimino acetate derivative. According to the invention, a methoxyimino acetate skeleton is used as a leading structure, and different pharmacophores are introduced on the basis of the leading structure, so that a series of novel methoxyimino acetate skeleton derivatives containing a chloroacetamide structure are synthesized. In-vitro tests of the compounds show that the compounds have excellent inhibition effects on plant pathogenic fungi such as fusarium graminearum, eggplant verticillium wilt, mango anthracnose pathogen, alternaria solani, sclerotinia sclerotiorum, muskmelon fusarium wilt pathogen and the like; the methoxyl acrylate derivative pesticide with high activity and novel action mechanism is expected to be developed.

Description

Technical Field

[0001] The present invention relates to the field of medicinal chemistry, and particularly relates to a novel methoxyiminoacetate derivative containing a chloroacetamide structure, a preparation method thereof, and an application thereof. Background Art

[0002] Plant fungal diseases are important factors restricting the high-quality and high-yield of crops, directly causing a decrease in crop yield and quality, and seriously endangering food security. It is estimated that fungal diseases have reduced the global annual yield of major food crops such as rice, wheat, corn, and potatoes by 125 million tons, with losses reaching up to tens of billions of US dollars. The food lost could feed an additional 600 million people annually. Currently, the prevention and control of major plant fungal diseases such as powdery mildew, rust, anthracnose, sheath blight, leaf spot, rice blast, late blight, and gray mold still mainly rely on chemical control. Among them, methoxyacrylate fungicides have developed very rapidly due to their high efficiency, broad spectrum, low toxicity, etc., and have great market potential. They are the third milestone fungicide variety after benzimidazoles and triazoles. However, due to the overuse of these agents in the production process, the resistance has gradually increased, and at the same time, the pesticide residues have increased, polluting and damaging the soil and ecological environment, and the control effect has decreased year by year. There is an urgent need to find new control agents.

[0003] Covalent drugs have the characteristics of strong binding force and long binding time, and can effectively avoid the off-target effect caused by the weak binding force of non-covalent drugs. Therefore, they have strong biological activity. The principle is to use the reactive groups (electrophilic sites) in their own structures to chemically react with specific nucleophilic amino acid residues such as cysteine (Cys) in the target protein to form covalent bonds, thereby irreversibly inhibiting the activity of the target protein. In the design of covalent drugs, the chloroacetamide structure is a commonly used reactive group. Such a structure can selectively undergo a nucleophilic substitution reaction with the sulfhydryl group on Cys of the target protein to form a covalent bond, thereby irreversibly inhibiting the enzyme activity, and is thus widely used in drug design. By introducing a chloroacetamide reaction group into the drug molecule, a strong covalent bond can be formed between the drug and the target, changing the original mechanism of action of the drug, and prolonging the drug-target interaction time, which is beneficial to improving the drug activity. Therefore, using the concept of covalent drug design, introducing a reactive fragment such as a chloroacetamide structure into the parent nucleus of traditional methoxyacrylate fungicides is expected to develop a class of methoxyacrylate derivatives with high activity and novel mechanisms of action. Summary of the Invention

[0004] In view of the deficiencies in the above problems, the present invention provides a novel methoxyiminoacetate derivative containing a chloroacetamide structure, or a stereoisomer thereof, or a salt thereof, or a solvate thereof. The compound has the structure shown in the general formula (I):

[0005]

[0006] R is selected from: hydrogen, deuterium, halogen, optionally substituted or unsubstituted alkyl, optionally substituted or unsubstituted alkoxy.

[0007] Preferably, the substitution is one or more substitutions of halogen, methyl, methoxy, trifluoromethyl.

[0008] The present invention also provides a synthetic method for preparing a novel methoxyiminoacetate derivative containing a chloroacetamide structure as described above, comprising the following steps:

[0009] (1) Mix (E)-methyl 2-methoxyimino-(2-o-tolyl)acetate, N-bromosuccinimide and azobisisobutyronitrile in carbon tetrachloride, heat and stir until the reaction is complete, filter off the solid insoluble matter, and after removing the solvent from the filtrate, purify and separate by column chromatography to obtain intermediate 1;

[0010] (2) Add potassium carbonate, substituted nitrophenol and N,N-dimethylformamide to the intermediate 1 obtained in step (1), stir and react at 85 °C, after the reaction is complete, filter, extract the filtrate with dichloromethane multiple times, dry and then remove the solvent and purify and separate by column chromatography to obtain intermediate 2;

[0011] (3) Add reduced iron powder, ammonium chloride and methanol to the intermediate 2 obtained in step (2), reflux and react at 65 °C, after the reaction is complete, filter, and after removing the solvent from the filtrate, purify and separate by column chromatography to obtain intermediate 3;

[0012] (4) Add potassium carbonate, chloroacetyl chloride and N,N-dimethylformamide to the intermediate 3 obtained in step (3), react at 0 °C, after the reaction is complete, quench the reaction with water and extract with dichloromethane multiple times, and then after removing the solvent from the filtrate, purify and separate by column chromatography to obtain the target compound.

[0013] The specific synthetic chemical equation is as follows:

[0014]

[0015] Correspondingly, the composition contains a novel methoxyiminoacetate compound containing chloroacetamide or its stereoisomer, or its salt or its solvate.

[0016] Preferably, the dosage form of the required composition is selected from: emulsifiable concentrate, powder, wettable powder, granule, aqueous solution, suspension, ultra-low volume spray, soluble powder, microcapsule, smoke agent, emulsion in water or water dispersible granule.

[0017] Correspondingly, the application of the compound shown in the above formula (I) or its stereoisomer or its salt or its solvate or the above composition in controlling agricultural pests and diseases.

[0018] Preferably, the agricultural pests and diseases are plant fungal diseases.

[0019] Preferably, the fungal disease is any one of Gibberella zeae, Verticillium dahliae, Colletotrichum gloeosporioides, Alternaria solani, Sclerotinia sclerotiorum, Fusarium oxysporum f. sp. melonis, Botryosphaeria dothidea, Fusarium oxysporum, Colletotrichum sublineolum, Alternaria alternata, Alternaria solani.

[0020] Compared with the prior art, the present invention has the following beneficial effects:

[0021] Using the methoxyiminoacetate skeleton as the lead structure, introducing the reactive group chloroacetamide structure into its aromatic side chain, and on this basis connecting different pharmacophores, a series of novel methoxyiminoacetate derivatives containing chloroacetamide structure are synthesized. In vitro test data show that the target compounds exhibit good inhibitory activity against plant pathogenic fungi (such as Alternaria solani, Gibberella zeae). In the in vitro experiment, compound 4 has good antibacterial activity against Gibberella zeae, Verticillium dahliae, Fusarium oxysporum f. sp. melonis, Alternaria solani and Colletotrichum gloeosporioides. When the concentration is 50 μg / mL, the inhibition rates are 70.3%, 72.1%, 55.2%, 80.4% and 54.9% respectively, which are better than the commercial drugs fenarimol and azoxystrobin. Among them, the EC 50 values of compound 4 against Alternaria solani and Gibberella zeae are both within 10 μg / mL. Among them, the EC 50 value of compound 4 against Alternaria solani is 0.05 μg / mL, and the EC 50 value against Gibberella zeae is 6.8 μg / mL. It can be seen that this series of compounds has excellent antibacterial activity. Detailed implementation manners

[0022] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts shall fall within the protection scope of the present invention. If not specifically specified, the technical means used in the implementation examples are conventional means well known to those skilled in the art.

[0023] Example 1

[0024] Intermediate 1: Preparation of methyl (E)-2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate.

[0025] The preparation route is as follows:

[0026]

[0027] The preparation process is as follows:

[0028] In a 500 mL three-necked flask, methyl (E)-2-(methoxyimino)-2-(o-tolyl)acetate (11.09 g, 0.054 mol) and 200 mL of dry carbon tetrachloride were added. The mixture was stirred and refluxed at 80 °C for 15 min. Then, NBS (10.4 g, 0.058 mol) and AIBN (1.7 g, 0.010 mol) were added thereto, and the mixture was refluxed for 12 h to complete the reaction. The completion of the reaction was monitored by TLC. After the reaction was completed, the reaction system was filtered by suction. The filtrate was partially concentrated to remove the solvent, 150 mL of water and 200 mL of dichloromethane were added for extraction, and then the organic phase was washed with water 5 times. The organic phase was dried over anhydrous sodium sulfate, filtered by suction, concentrated to remove the solvent, and then mixed with silica gel. After separation and purification by column chromatography, methyl (E)-2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate was obtained.

[0029] Example 2

[0030] Intermediate 2: Preparation of methyl (E)-2-(methoxyimino)-2-(2-((2-methyl-5-nitrophenoxy)methyl)phenyl)acetate.

[0031] The preparation route is as follows:

[0032]

[0033] The preparation process is as follows:

[0034] In a 100 mL round-bottomed flask, methyl (E)-2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate (3.6 g, 0.013 mol), 2-methyl-4-nitrophenol (2.1 g, 0.014 mol) and 50 mL of dry DMF were added. The reaction mixture was stirred in an ice bath for 10 min to dissolve the reactants, and then 60% sodium hydride (0.55 g, 0.023 mol) was added to the system in three portions. After the addition of sodium hydride was completed, the reaction system was heated to 80 °C and stirred for 2 h to complete the reaction. The completion of the reaction was monitored by TLC. 40 mL of ice water was added to the reaction system, and then the pH was adjusted to neutral with dilute hydrochloric acid. Then, 150 mL of dichloromethane was added for extraction. The organic phase was washed with water 10 times, 80 mL each time. Then, the organic phase was dried over anhydrous sodium sulfate, filtered by suction, concentrated to remove the solvent, and mixed with silica gel. After separation and purification by column chromatography, methyl (E)-2-(methoxyimino)-2-(2-((2-methyl-5-nitrophenoxy)methyl)phenyl)acetate was obtained.

[0035] For other nitro intermediate compounds, corresponding raw materials or substituents were used and synthesized with reference to the steps of Example 2.

[0036] Example 3

[0037] Intermediate 3: Methyl (E)-2-(2-((5-amino-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate.

[0038] The preparation route is as follows:

[0039]

[0040] The preparation process is as follows:

[0041] Add methyl (E)-2-(methoxyimino)-2-(2-(2-methyl-5-nitrophenoxy)methyl)phenyl)acetate (3.1 g, 0.009 mol), ammonium chloride (2.30 g, 0.043 mol), methanol (60 mL) and water (10 mL) into a 250 mL three-necked flask, and reflux and stir at 65 °C for 10 min to dissolve the raw materials. Then add iron powder (2.89 g, 0.005 mol) into the reaction system, and reflux and react at 65 °C for 2 h to complete the reaction, and monitor the completion of the reaction by TLC. Filter the reaction system while it is hot, concentrate the filtrate to remove the solvent, then add 80 mL of dichloromethane and 50 mL of water for extraction, and wash the organic phase twice with 50 mL of water each time. Dry the organic phase with anhydrous sodium sulfate, filter it, concentrate the filtrate to remove the solvent, mix the sample with silica gel, and separate and purify it by column chromatography to obtain methyl (E)-2-(2-((5-amino-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate.

[0042] For other amino intermediate compounds, use the corresponding raw materials or substituents and synthesize them according to the steps of Example 3.

[0043] Example 4

[0044] Preparation of the target compound: Methyl (E)-2-(2-((5-(2-chloroacetamido)-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate.

[0045] The preparation route is as follows:

[0046]

[0047] The preparation process is as follows:

[0048] Add (E)-methyl 2-(2-((5-amino-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate (0.75 g, 0.002 mol), anhydrous potassium carbonate (0.47 g, 0.003 mol) and anhydrous DMF (12 mL) to a 50 mL dry round-bottom flask. Stir for 10 min in an ice bath, then slowly add chloroacetyl chloride (0.003 mol, 0.22 mL). React for 30 min in an ice bath until the reaction is complete, and monitor the reaction completion by TLC. Add 80 mL of dichloromethane and 50 mL of ice water to the reaction system for extraction, and then wash the organic phase with water 8 times, 50 mL each time. Dry the organic phase with anhydrous sodium sulfate, filter by suction, concentrate to remove the solvent, mix with silica gel, and separate and purify by column chromatography to obtain (E)-methyl 2-(2-((5-(2-chloroacetamido)-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate.

[0049] For other target compounds, use the corresponding raw materials or substituents and synthesize according to the steps of Example 4.

[0050] The structures, 1H NMR and 13C NMR data of other synthesized imidazopyrimidinone skeleton compounds are shown in Table 1, and the physical and chemical properties are shown in Table 2.

[0051] Table 1: 1H NMR, 13C NMR and high-resolution mass spectrometry data of the compounds

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059] Table 2: Physical and chemical properties of the target compounds

[0060] Number Physical form Yield Melting point 1 White solid 71.5％ 151-153℃ 2 White solid 49.7％ 104-105℃ 3 White solid 65.4％ 128-130℃ 4 Pink solid 42.9％ 133-135℃ 5 White solid 73.7％ 125-127℃ 6 Yellow solid 75.4％ 105-106℃ 7 White solid 54.2％ 146-148℃ 8 White solid 76.9％ 128-129℃ 9 White solid 62.7％ 112-114℃ 10 White solid 77.3％ 158-160℃ 11 Pink solid 45.1％ 129-131℃ 12 White solid 69.3％ 159-161℃ 13 Pink solid 49.6％ 139-141℃ 14 White solid 77.6％ 144-146℃ 15 White solid 67.1％ 147-148℃ 16 Grey solid 65.4％ 146-148℃ 17 Yellow solid 53.5％ 126-128℃ 18 White solid 75.3％ 143-145℃ 19 White solid 46.5％ 189-191℃ 20 White solid 62.1％ 119-121℃ 21 White solid 67.8％ 135-137℃ 22 White solid 46.9％ 182-183℃ 23 White solid 58.3％ 114-116℃ 24 Yellow solid 69.5％ 150-152℃ 25 White solid 48.6％ 121-123℃ 26 White solid 72.1％ 116-117℃ 27 White solid 57.5％ 135-137℃ 28 White solid 66.4％ 126-128℃

[0061] Example 5

[0062] Applications of the target compounds.

[0063] The mycelial growth rate method, also known as the toxic medium method, is one of the conventional methods for measuring the toxicity of fungicides. The main principle is to mix the test agent with the culture medium, and measure the toxicity of the agent by the growth rate of the colony on the toxic culture medium. In this example, Gibberella zeae, Verticillium dahliae, Fusarium oxysporum f. sp. melonis, Alternaria solani, Colletotrichum gloeosporioides, Sclerotinia sclerotiorum, and Rhizoctonia solani were used as test objects. A DMSO (1%) solution without any compound was used as the blank control, and the commercial fungicides fenhexamid and azoxystrobin were used as the positive controls. The specific operations are as follows: 1) Accurately weigh 5 mg of the compound into a 1.5 mL centrifuge tube, add 1 mL of DMSO and dissolve it thoroughly to obtain the experimental liquid. Take 0.5 mL and add it to 4.5 mL of aqueous solution containing Tween 20 (0.1%). After mixing evenly, add it to 45 mL of PDA culture medium, mix well, pour it into 3 plates, and after cooling, inoculate with fungal discs; 2) When the mycelium in the blank control group grows to about 5.0 cm, use the cross method to measure the colony diameter of the control group and each agent treatment group; 3) The inhibition effect of the compound is calculated according to the following formula: Inhibition efficiency (%) = [(L 0 -L) / (L 0 -0.5)]×100%; where L 0 represents the diameter of the fungal growth in the blank control, L represents the diameter of the fungal growth treated with the compound, and 0.5 is the diameter of the inoculated fungal disc. According to the above method, the experimental results of the target compounds in Table 1 above are shown in Table 3. It can be seen from Table 3 that in the in vitro experiment, compound 4 has good antibacterial activity against Alternaria solani, Gibberella zeae, Verticillium dahliae, Colletotrichum gloeosporioides, and Fusarium oxysporum f. sp. melonis. When the concentration is 50 μg / mL, the inhibition rates are 80.4%, 70.3%, 72.1%, 54.9%, and 55.2% respectively, all better than the commercial drug fenhexamid. It can be seen that this series of compounds can be used to prepare pesticides against plant pathogenic fungi.

[0064] Table 3: Inhibitory activity of compounds against plant pathogenic fungi (50 μg / mL)

[0065]

[0066]

[0067]

[0068] Example 6

[0069] Application of the target compound.

[0070] EC 50 value of the compound against plant pathogenic fungi.

[0071] To further explore the activity of the compounds, according to the primary screening results, compounds with excellent antibacterial activity were selected for EC 50 screening. The specific operations are as follows: 1) Accurately weigh 5 mg of the target compound into a 1.5 mL centrifuge tube, add 1 mL of DMSO and mix well. Take out 0.5 mL of the solution as the stock solution of the first concentration (50 μg / mL). After adding 0.5 mL of DMSO to the remaining 0.5 mL of the solution, mix well with a mixer, and then take out 0.5 mL of the solution as the stock solution of the second concentration (25 mg / L). Configure the stock solutions of different concentrations in the way of equal ratio of concentrations; 2) Add the configured stock solutions into 4.5 mL of sterile aqueous solution respectively, and shake well to dissolve them completely. Add the solutions of different concentrations into 45 mL of PDA medium in turn, mix well, and dispense them into 3 petri dishes. After cooling, inoculate with bacterial cakes; 3) When the mycelium grows to about 5.0 cm, measure the mycelium diameter by the cross method, calculate the inhibition rate, take the logarithm of the concentration and make a linear regression equation with the inhibition rate, so as to obtain its virulence regression equation and EC 50 value; According to the above method, the EC 50 values, regression equations and R 2 values of some target compounds against Alternaria solani are shown in Table 4-9. It can be seen from Table 4-9 that in in vitro tests, some target compounds showed good inhibitory activity against plant pathogenic fungi (such as Alternaria solani, Gibberella zeae, Colletotrichum gloeosporioides and Fusarium oxysporum f. sp. melonis). Among them, the EC 50 of compound 4 against Alternaria solani is 0.05 μg / mL, the EC 50 against Gibberella zeae is 6.8 μg / mL, the EC 50 against Colletotrichum gloeosporioides is 17.4 μg / mL, and the EC 50 against Fusarium oxysporum f. sp. melonis is 21.3 μg / mL.

[0072] Table 4: EC 50 values of some target compounds against Alternaria solani

[0073] Compound. <![CDATA[EC 50 (mg / L)]]> Regression equation <![CDATA[R 2 > 1 1.86±0.18 y = 0.3346x + 4.91 0.9821 2 19.13±0.79 y = 0.6733x + 4.137 0.9732 3 20.40±1.18 y = 0.8391x + 3.9011 0.9636 4 0.05±0.01 y = 0.5282x + 5.3468 0.9781 6 40.23±1.56 y = 2.0012x + 1.7889 0.9730 12 0.27±0.03 y = 0.3451x + 5.1974 0.9916 14 5.47±0.35 y = 0.6402x + 4.5275 0.9952 15 0.10±0.02 y = 0.246x + 5.2435 0.9939 16 0.77±0.22 y = 0.3671x + 5.0407 0.9820 23 0.91±0.02 y = 1.0128x + 5.0425 0.9698 26 25.21±1.11 y = 1.3715x + 3.0777 0.9909 27 22.66±0.40 y = 1.2283x + 3.3354 0.9363 28 23.05±0.41 y = 1.9402x + 2.3561 0.9123 ZJ0712 0.06±0.01 y = 0.2562x + 5.4579 0.9823 Azoxystrobin 0.04±0.01 y = 0.4116x + 5.5613 0.9306

[0074] Table 5: EC 50 values of some target compounds against Gibberella zeae

[0075]

[0076]

[0077] Table 6: Some target compounds against Verticillium dahliae

[0078] Compound. <![CDATA[EC 50 (mg / L)]]> Regression equation <![CDATA[R 2 > 4 21.5±1.2 y = 0.6055x + 4.1938 0.9641 23 29.8±1.6 y = 1.4938x + 2.7974 0.9902 ZJ0712 18.6±1.4 y = 0.4912x + 4.3767 0.9900 Azoxystrobin 9.1±0.3 y = 0.7464x + 4.284 0.9811

[0079] Table 7: EC of some target compounds against Colletotrichum gloeosporioides 50 value

[0080] Compound. <![CDATA[EC 50 (mg / L)]]> Regression equation <![CDATA[R 2 > 4 17.4±1.7 y = 0.3776x + 4.5318 0.9891 ZJ0712 ＞50 - - Azoxystrobin 24.2±1.6 y = 0.5879x + 4.1869 0.9896

[0081] Table 8: EC of some target compounds against Fusarium oxysporum f. sp. melonis 50 value

[0082]

[0083]

[0084] Table 9: EC of some target compounds against Sclerotinia sclerotiorum 50 value

[0085] Compound. <![CDATA[EC 50 (mg / L)]]> Regression equation <![CDATA[R 2 > 4 18.2±1.2 y = 1.404x + 3.2322 0.9864 7 13.4±1.3 y = 1.9264x + 2.8272 0.9898 13 11.4±1.1 y = 1.5339x + 3.381 0.9759 16 19.7±0.6 y = 2.52x + 1.7375 0.9834 23 9.2±1.0 y = 1.3143x + 3.7326 0.9832 24 18.4±2.8 y = 2.3597x + 2.0159 0.9998 ZJ0712 3.8±0.6 y = 0.8379x + 4.5116 0.9732 Azoxystrobin 4.8±0.7 y = 0.9864x + 4.3265 0.9673

[0086] The embodiments described above are only descriptions of the preferred embodiments of the present invention, and do not limit the scope of the present invention. Without departing from the design spirit of the present invention, various deformations and improvements made by those of ordinary skill in the art to the technical solutions of the present invention shall fall within the protection scope determined by the claims of the present invention.

[0087] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and are not restrictive. Although the present invention has been described in detail with reference to the preferred embodiments, those of ordinary skill in the art should understand that the technical solutions of the present invention can be modified or equivalently replaced without departing from the purpose and scope of the technical solutions of the present invention, and they should all be covered by the scope of the claims of the present invention. The protection scope of this application should be subject to the protection scope of the claims.

Claims

1. A novel methoxyiminoacetic acid ester derivative containing a chloroacetamide structure, characterized in that: The compound has a structure as shown in the general formula (I): R is selected from the group consisting of hydrogen, deuterium, halogen, optionally substituted or unsubstituted alkyl, and optionally substituted or unsubstituted alkoxy.

2. The novel methoxyiminoacetic acid ester derivative containing a chloroacetamide structure according to claim 1, characterized in that: The substitution refers to one or more substitutions selected from the group consisting of hydrogen, deuterium, halogen, methyl, methoxy, and trifluoromethyl.

3. The novel methoxyiminoacetic acid ester derivative containing a chloroacetamide structure according to claim 1, characterized in that: R is selected from the group consisting of: hydrogen, halogen, methyl, methoxy, trifluoromethyl.

4. A method for preparing a novel methoxyiminoacetic acid ester derivative containing a chloroacetamide structure according to any one of claims 1 to 3, characterized in that: The chemical formula for the synthesis is as follows:

5. A composition, characterized in that The composition contains a novel methoxyimino derivative containing chloroacetamide as described in any one of claims 1 to 3 or its stereoisomer, or its salt, or its solvate.

6. The dosage form of the composition as claimed in claim 5 is selected from: emulsifiable concentrate, dust, wettable powder, granule, aqueous solution, suspension, ultra-low volume spray, soluble powder, microcapsule, smoke agent, aqueous emulsion or water-dispersible granule.

7. Use of the compound represented by formula (I) according to claim 1 or 2, or its stereoisomer, or its salt, or its solvate, or the composition according to claim 5 or 6 in controlling agricultural pests and diseases.

8. The use according to claim 7, characterized in that: The agricultural pests and diseases are plant fungal diseases.

9. The use according to claim 8, characterized in that: The fungal disease is any one of wheat fusarium wilt, eggplant verticillium wilt, mango anthracnose, tomato early blight, rapeseed sclerotinia, melon wilt, Botrytis cinerea, Fusarium oxysporum, sorghum thorny spore fungus, tobacco brown spot pathogen, and solanum solani.

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