A fungicidal and bactericidal compound derived from marine fungi and a preparation method thereof

Abstract

The application belongs to the field of secondary metabolites of marine fungi, and particularly relates to a marine fungus-derived insecticidal and fungicidal compound and a preparation method thereof. The insecticidal and fungicidal compound has the structure shown in compounds 1-3.

Description

Technical Field

[0001] This invention belongs to the field of marine fungal secondary metabolites, specifically relating to an insecticidal and fungicidal compound derived from marine fungi and its preparation method. Background Technology

[0002] Mangrove plants grow in the tropical and subtropical intertidal zone, where the environment is characterized by high pressure, high salinity, and low oxygen. This environment gives their endophytic fungi unique metabolic pathways, enabling them to produce compounds with novel structures and diverse biological activities. Their metabolites possess various medicinal values, including insecticidal, fungicidal, and antioxidant properties, making them a potential resource for microbial drug development. Therefore, mangrove endophytic fungi will become an important resource for the research and development of biopesticides. The applicant previously obtained a series of antitumor active indole diterpenoid compounds from the marine fungus *Eupenicillium* sp. HJ002 (Chinese patent applications: 201710416276.1 and 201710417257.0), and further research on the marine fungus *Eupenicillium* sp. HJ002 yielded a series of insecticidal and fungicidal compounds. Summary of the Invention

[0003] This invention provides a compound or a pesticide-acceptable salt thereof, characterized in that the compound has the structure shown in compounds 1-3 below:

[0004]

[0005] Another embodiment of the present invention provides a method for preparing compounds 1, 2 and / or 3, characterized by comprising the following steps:

[0006] (1) Prepare seed culture medium by inoculating marine fungus Eupenicillium sp.HJ002 into the seed culture medium and culturing at 26-28℃ for 3-4 days to obtain seed culture solution.

[0007] (2) Inoculate the seed culture medium obtained in step (1) into the fermentation medium and culture at room temperature for 28 to 30 days to obtain the fermentation product;

[0008] (3) Extract the fermentation product obtained in step (2) with ethyl acetate, extract 2 to 4 times, combine the ethyl acetate phases and concentrate under reduced pressure to obtain the extract;

[0009] (4) The extract obtained in step (3) was subjected to vacuum silica gel column chromatography with gradient elution using petroleum ether-ethyl acetate as the eluent. The elution gradients were 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, and 0:100. Two column volumes were collected for each gradient, and the extract was divided into 6 fractions according to polarity. Fraction 1 was obtained from gradients 100:0 to 90:10, and fractions 80:20 to 70:30 were obtained from gradients 80:20 to 70:30. Fraction 2 was obtained by elution at 0: gradient 60:40–50:50, fraction 3 by elution at 60:40–50:50, fraction 4 by elution at 40:60–30:70, fraction 5 by elution at 20:80–10:90, and fraction 6 by elution at 0:100. Fraction 3 was first subjected to normal-phase silica gel column chromatography with a mixed solvent of petroleum ether and ethyl acetate in the ratio of 20:1 to 10:1, eluting for 2–5 column volumes. After concentration under reduced pressure, it was prepared by high-performance liquid chromatography (HPLC) using a Waters C18 column (9.4 × 250 mm, 7 μm), a flow rate of 2 mL / min, and a mobile phase of MeOH:H2O in the ratio of 10:90–20:80, yielding compounds 1, 2, and / or 3.

[0010] The proportions of the eluent or mobile phase are all volume ratios; the seed culture medium is a conventional seed culture medium in the art, preferably potato dextrose water medium (PDB medium); the fermentation medium is a conventional fermentation medium in the art, preferably a solid rice medium (the preferred formulation is 50g rice, 60g water, 0.5g sea salt and 1.5g peptone per 1L conical flask).

[0011] Another embodiment of the invention provides the use of the marine fungus Eupenicillium sp. HJ002 in the preparation of compounds 1, 2 and / or 3.

[0012] Another embodiment of the present invention provides the application of compounds 1, 2 and / or 3 in the control of agricultural pests and diseases. The agricultural pests and diseases are preferably caused by one or more of the following: banana anthracnose fungus, tomato gray mold fungus, rapeseed sclerotinia sclerotinia, and southern root-knot nematode.

[0013] Another embodiment of the present invention provides the use of the above compounds 1, 2 and / or 3 in the preparation of antioxidants.

[0014] Another embodiment of the present invention provides a pesticide composition, characterized in that the pesticide composition uses compounds 1, 2 and / or 3 or their pesticide-acceptable salts as active ingredients. The pesticide composition may also include pesticide-acceptable excipients. The pesticide composition may also include other insecticidal and fungicidal active ingredients.

[0015] Another embodiment of the present invention provides an antioxidant, characterized in that the antioxidant uses compounds 1, 2 and / or 3 or their pharmaceutically acceptable salts as active ingredients. The antioxidant may also include other antioxidants.

[0016] The marine fungus Eupenicillium sp. HJ002 involved in this invention is a known species, and its preservation information is as follows: Depository Institution: China General Microbiological Culture Collection Center (CGMCC); Address: No. 3, Courtyard 1, Beichen West Road, Chaoyang District, Beijing, Institute of Microbiology, Chinese Academy of Sciences; Deposit Date: December 21, 2016; Deposit Number: CGMCC No. 13373; Classification: Eupenicillium sp.; It has been disclosed in the applicant's previous Chinese patent applications Nos. 201710416276.1 and 201710417257.0. Attached Figure Description

[0017] Figure 1 This is a plate diagram of the antifungal activity of compound 1. Note: XT: Banana anthracnose pathogen, test concentration 10-50 μg / mL; Tomato gray mold pathogen: test concentration 20-60 μg / mL; YC: Rapeseed sclerotinia pathogen, test concentration 10-50 μg / mL; CK is a blank control.

[0018] Figure 2 This is a diagram showing the efficacy of compound 1 against southern root-knot nematodes in potted plants.

[0019] Figure 3 It is compounds 1-3 1 H- 1 H COSY and HMBC related signal diagram.

[0020] Figure 4 This is the NOESY spectrum of compounds 1-2.

[0021] Figure 5 These are the experimental ECD spectra of compounds 1-2.

[0022] Figure 6 It is compound 1 1 H NMR spectrum.

[0023] Figure 7 It is compound 1 13 C NMR spectrum.

[0024] Figure 8 This is the 135°-DEPT plot of compound 1.

[0025] Figure 9 This is the HMQC diagram of compound 1.

[0026] Figure 10 It is compound 1 1 H- 1 H COSY diagram.

[0027] Figure 11 This is the HMBC diagram of compound 1.

[0028] Figure 12 This is the NOESY diagram of compound 1.

[0029] Figure 13 This is the HR-ESI-MS chromatogram of compound 1.

[0030] Figure 14 It is compound 1 1 H NMR spectrum.

[0031] Figure 15 It is compound 2. 13 C NMR spectrum.

[0032] Figure 16 This is the 135°-DEPT plot of compound 2.

[0033] Figure 17 This is the HMQC diagram of compound 2.

[0034] Figure 18 It is compound 2. 1 H- 1 H COSY diagram.

[0035] Figure 19 This is the HMBC diagram of compound 2.

[0036] Figure 20 This is the NOESY diagram of compound 2.

[0037] Figure 21 This is the HR-ESI-MS chromatogram of compound 2.

[0038] Figure 22 It is compound 3. 1 H NMR spectrum.

[0039] Figure 23 It is compound 3. 13 C NMR spectrum.

[0040] Figure 24 This is the 135°-DEPT plot of compound 3.

[0041] Figure 25 This is the HMQC diagram of compound 3.

[0042] Figure 26 This is the HMBC diagram of compound 3.

[0043] Figure 27 This is the HR-ESI-MS image of compound 3. Detailed Implementation

[0044] To facilitate a further understanding of the present invention, the following embodiments are provided for more detailed description. However, these embodiments are only for a better understanding of the invention and are not intended to limit the scope or implementation principles of the invention. The implementation of the present invention is not limited to the following.

[0045] Example 1

[0046] (1) The fungal strain Eupenicillium sp. HJ002 was inoculated into potato dextrose water medium (PDB medium). Each 1L Erlenmeyer flask contained 350mL of PDB medium. A total of 5 flasks of seed culture were fermented at 28℃ for 3 days to obtain seed culture solution.

[0047] (2) Take an appropriate amount of the seed culture solution obtained in step (1) and inoculate it into an Erlenmeyer flask containing fermentation culture medium (solid rice culture medium, formula: each 1L Erlenmeyer flask contains 50g rice, 60g water, 0.5g sea salt and 1.5g peptone). Inoculate a total of 200 flasks and incubate at room temperature for 30 days to obtain the fermentation product.

[0048] (3) Extract the fermentation product obtained in step (2) three times with an appropriate amount of ethyl acetate; combine the ethyl acetate phases and concentrate under reduced pressure to obtain an extract.

[0049] (4) The extract obtained in step (3) was subjected to vacuum silica gel column chromatography with gradient elution using petroleum ether-ethyl acetate as the eluent. The elution gradients were 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90, and 0:100. Two column volumes were collected for each gradient, and the extract was divided into 6 fractions according to polarity. Fraction 1 was obtained from gradients 100:0 to 90:10, and fractions 80:20 to 70:30 were obtained from gradients 80:20 to 70:30. Fraction 2 was obtained by elution at 0: gradient 60:40–50:50, fraction 3 by elution at 60:40–50:50, fraction 4 by elution at 40:60–30:70, fraction 5 by elution at 20:80–10:90, and fraction 6 by elution at 0:100. Fraction 3 was first subjected to normal-phase silica gel column chromatography with a mixed solvent of petroleum ether and ethyl acetate in the ratio of 20:1 to 10:1 for 2–5 column volumes. After concentration under reduced pressure, it was prepared by high-performance liquid chromatography (HPLC) using a Waters C18 column (9.4 × 250 mm, 7 μm), a flow rate of 2 mL / min, and a mobile phase of MeOH:H2O in the ratio of 10:90–20:80, yielding compounds 1 (60.3 mg), 2 (7.4 mg), and / or 3 (5.6 mg).

[0050]

[0051] The structural confirmation data for compounds 1-3 are as follows:

[0052] Table 1. Proton NMR spectral data of compounds 1-3

[0053]

[0054]

[0055] a DMSO-d6, b CDCl3, c CD3OD, d 400 HMz

[0056] Table 2. Carbon spectral data of compounds 1-3

[0057]

[0058] a DMSO-d6, b CDCl3

[0059] Compound 1: White powder. High-resolution mass spectrometry (HR-ESI-MS) shows a quasi-molecular ion peak [M+Na] at m / z 245.0781. +Based on the proton and carbon spectral data, the molecular formula of this compound is deduced to be C64. 12 H 14 O4 has an unsaturation degree of 6. 1 The H-NMR spectrum (Table 1) indicates the presence of one olefinic proton signal [δ]. H [6.08(s)], 1 methylene hydrogen signal δ H 3.03 (m), 1 hydroxymethylene hydrogen signal [δ] H 3.73 (dd, J = 12.0, 5.6 Hz) and 3.42 (m)], two methylene hydrogen signals [δ H 2.01 (dd, J = 2.8, 2.4 Hz) and 1.69 (m)] and [δ H [1.88(m) and 1.37(m)], two methyl signals [δ] appear in the high field region. H 2.17(s) and δ H 1.44(s)]; combined 13 The C-NMR (Table 2) and DEPT 135° spectra show that this compound has 12 resonance carbon signals, including one ester carbonyl carbon signal δ. C 161.1, 4 olefin carbon signals δ C (165.9, 162.5, 99.5, and 98.9), one quaternary carbon signal δ C (99.9), 1 hydroxymethylene carbon signal δ C (59.2), 2 methylene carbon signals δ C (33.5, 27.4), 1 methylene carbon signal δ C (22.8), 2 methyl carbon signals δ C (26.8, 19.3).

[0060] according to 1 H- 1 H COSY spectrum ( Figure 3 The given CH2(7)-CH(6)-CH2(9)-CH2(10) linker fragments, combined with the HMBC spectrum, show the correlations between H-11 to C-4 / C-5, H-4 to C-2 / C-3 / C-5, H-6 to C-1 / C-2 / C-3, H-12 to C-7 / C-8, and H-10 to C-6 / C-8. Further analysis using the NOESY spectrum... Figure 4It can be seen that H-6 and H-12 are correlated, thus determining that the hydrogen atoms of H-6 and H-12 are oriented in the same direction. Based on the above 1D / 2D NMR data, the planar configuration and relative configuration of this compound were determined. To determine the absolute configuration of compound 1, the theoretical ECD spectra of the two possible stereoisomers, 6R, 8R and 6S, 8S, were calculated by TDDFT. The results show that the calculated ECD curves of the 6R, 8R isomers are in good agreement with the experimental data. Figure 5 Therefore, the absolute configuration of compound 1 was determined to be 6R, 8R, and it was named Eupenicillmarine A.

[0061] Compound 1: [α] 25 D +127.9(c 0.10,MeOH); UV(MeOH)λ max (logε)287,212nm;IR(KBr)ν max 1701, 1620, 1607cm -1 ;CD(c 0.1,MeOH)λ max (Δε)275(-6.87)nm; HR-ESI-MS m / z:245.0781[M+Na] + ,(C 12 H 14 O4Na + ,calcd.for 245.0784).

[0062] Compound 2: A yellow oily substance. High-resolution mass spectrometry (HR-ESI-MS) and 1D and 2D NMR data indicate that the molecular formula of this compound is C2. 13 H 16 O4, with an unsaturation degree of 6, was compared with the 1D NMR data of compound 1 (Tables 1 and 2). The carbon spectra showed a high degree of similarity, suggesting a possible series of compounds, and both possess the same 6 / 6 / 6 heterocyclic tricyclic skeleton. The main difference lies in the [δ] of compound 2. H 1.86(s), δ C A methyl group exists at position 9.1(CH3)], [δ H There is no aromatic proton signal at 6.08(s). Based on the correlation signal in the HMBC spectrum, there is a correlation signal from H-13 to C-3 / C-4 / C-5. Figure 3 This indicates that a methyl group is attached to C-4. Combined with the NOESY spectrum, a correlation signal is observed between H-6 and H-12, further confirming that this relative configuration is consistent with compound 1. Based on CD test data ( Figure 5It can be seen that a negative Cotton effect is observed at 282 nm, and the absolute configurations on C-6 and C-12 are calculated by ECD. Figure 5 The structure was determined to be 6S,8S. Therefore, compound 2 was named Eupenicillmarine B.

[0063] Compound 2: [α] 25 D +54.9(c 0.10,MeOH); UV(MeOH)λ max (logε)288,208nm;IR(KBr)ν max 1705, 1696, 1644cm -1 ;CD(c 0.1,MeOH)λ max (Δε)282(+10.09)nm; HR-ESI-MS m / z:259.0938[M+Na] + ,(C 13 H 16 O4Na + ,calcd.for 259.0941).

[0064] Compound 3: A yellow oily substance. Based on the molecular ion characteristics observed by high-resolution mass spectrometry (HR-ESI-MS), a quasi-molecular ion peak [M+K] is given at m / z 285.0696. + The molecular formula of the compound was deduced to be C. 13 H 14 N₂O₃ has an unsaturation degree of 8. 1 The 1H-NMR spectrum (Table 1) shows that this compound has three olefin hydrogen signals [8.16(s), 6.28(s), and 5.85(s)] and one methylene hydrogen signal δ. H 3.40(s), at δ H Two methyl hydrogen signals exist at (1.0-2.5) [2.32(s) and 2.16(s)]; binding 13 The C-NMR (Table 2) and DEPT 135° spectra show that this compound has 13 resonance carbon signals, including one ketone carboxyl carbon signal δ. C 181.9, 8 olefin carbon signals δ C (168.5, 167.6, 160.7, 154.9, 126.4, 113.5, 102.3 and 100.0), a quarterly carbon signal δ C 166.2, 1 methylene carbon signal δ C 20.0, 2 methyl carbon signals δ C(20.0 and 19.8). Based on the HMBC spectrum, H-2 to C-4 / C-5, H-5 to C-1 / C-2 / C-4, H-6 to C-1 / C-2 / C-4 / C-7 / C-8 / C-11, H-9 / H-11 to C-7 / C-8, and H-13 to C-9 / C-10 are correlated. Combined with HR-ESI-MS data, it was determined that the 2,4-dihydroxy-5-methylpyridine fragment passes through one methylene [δ] C 20.0 and δ H 3.40(s)] is partially linked to 2-methyl-4-pyridone ( Figure 3 Based on the above 1D / 2D NMR data, the planar structure of the compound was determined. Therefore, the structure of compound 3 was determined to be a novel α-pyridone derivative, and it was simply named Eupenicillmarine C.

[0065] Compound 3: [α] 25 D +23.6(c 0.10,MeOH); UV(MeOH)λ max (logε)255,207nm;IR(KBr)ν max 3546,3432,1809,1644,1634,1617,1608cm -1 ;HR-ESI-MS m / z:285.0696[M+K] + ,(C 13 H 14 N2O3K + ,calcd.for 285.0636).

[0066] Example 2 Antioxidant Activity Test

[0067] (1) Testing instruments and materials: Total antioxidant capacity test kit, PBS buffer solution, 96-well plate, microplate reader, EP tubes and pipettes, etc.

[0068] (2) Dilute the working stock solution in step (1) with PBS buffer to prepare ABTS working solution (35-50 times dilution), and then use a microplate reader to test its absorbance range at 734 and 405 nm as follows:

[0069] A ABTS工作液 -A PBS =A 734 (0.7±0.05); A ABTS工作液 -A PBS =A 405 (around 1.4)

[0070] (3) Antioxidant capacity test:

[0071] Antioxidant activity of compounds 1-3 was tested using a total antioxidant capacity assay kit with PBS as the buffer solution. Sample concentrations were prepared at five gradients: 0.75, 0.5, 0.25, 0.125, and 0.0625 mg / mL. For each test, 200 μL of ABTS working solution, 10 μL of the test sample (experimental group), 10 μL of PBS (blank group), and 10 μL of Ltrox (positive control group) were added to a 96-well plate. The test was performed in triplicate. After standing for 5-7 minutes, the absorbance was measured at 734 or 405 nm. The inhibition rate of the test sample was calculated using the following formula: Inhibition rate (%) = [(A...] blank -A sample ) / A blank [×100%, IC calculated using GraphPad Prism 9 software] 50 value.

[0072] (4) Experimental results:

[0073] Table 3 shows the antioxidant activity results of the compounds.

[0074]

[0075] Example 3 Antifungal activity test

[0076] (1). Experimental instruments and materials: constant temperature incubator, pipette, electronic balance, 0.5cm diameter hole punch, ruler, sealing film, tweezers, autoclave, PDA medium, dimethomorph, analytical grade methanol, banana anthracnose pathogen (Calletotrichummusae), tomato gray mold pathogen (Botrytis cinerea), and rapeseed sclerotinia pathogen (Sclerotiniasclerotiorum).

[0077] (2). The mycelial growth rate inhibition method was used to detect the in vitro mycelial inhibition rate (Journal of Agricultural and Food Chemistry. 2024, 72(10): 5258-5268.). 1 mg of the test sample was completely dissolved in a small amount of methanol. The test sample was then mixed with 50 mL of PDA medium to final concentrations of 10, 15, 20, 30, 40, 50, and 60 μg / mL, respectively, and poured evenly into sterilized plates. The activated plant pathogen was then punched into mycelial cakes using a sterilized puncher (0.5 cm in diameter). The mycelial cakes were inoculated into the center of sterile PDA plates. An equal volume of methanol without the compound was used as a blank control, and dimethomorph was used as a positive control. The treatments and controls were incubated in the dark at (27±1)℃ for 2-6 days. The experiment was terminated when the pathogen in the control group reached a colony diameter of 5.5 cm or more. All treatments were repeated three times. Using a standard ruler, measure the diameter (cm) of the inhibition zone using the cross-hatching method, and take the average value. The mycelial growth inhibition rate = (control group colony diameter - treatment group colony diameter) / (control group colony diameter - 0.5) × 100%; then use SPSS software to calculate its EC50. 50 Values ​​and independent regression equations.

[0078] (3). Experimental results Figure 1 ):

[0079] Table 4 shows the results of the anti-plant pathogen activity of compound 1.

[0080]

[0081] Example 4: Activity test against southern root-knot nematodes:

[0082] (1) Test instruments and materials: 6-well test plate, counter, glass slide, 2% -80 Tween water, sonicator, stir bar, pipette, southern root-knot nematode (Meloidogyne incognita Chitwood).

[0083] (2) The insecticidal activity of compounds 1-3 against southern root-knot nematodes was determined using the poisoning method described in the literature (Journal of Agricultural and Food Chemistry. 2023, 71(36): 13209-13219.). The initial screening concentration of the samples was 50 μg / mL, the total volume of each well plate was 2 mL of Tween water, and the number of nematodes in each well was 150-200. Avermectin was used as a positive control, and water was used as a blank control. Each agent was tested in triplicate and repeated three times. The mortality of nematodes was observed and counted 24, 48, and 72 h after application, and the corrected mortality rate of nematodes was calculated using the following formula:

[0084] Verified mortality rate (%) = Mortality rate - Blank mortality rate / (1 - Blank mortality rate) × 100%

[0085] Table 5. Corrected mortality rates (EC) of compounds against southern root-knot worm at different time points. 50 (μg / mL) Activity results

[0086]

[0087] Example 5: Potted plant experiment on resistance to southern root-knot nematodes:

[0088] According to the method of Zhang et al. (Journal of Agricultural and Food Chemistry.2023,71(36):13209-13219.), the pot efficacy test of compound 1 against southern root-knot nematodes was conducted. The specific operation steps are as follows: Select pepper seedlings with consistent growth trends and transplant them into flower pots, one seedling per pot, and inoculate about 2000 J2 stage nematodes. One week after transplanting, the prepared solutions of compound 1 at concentrations of 10, 30, and 60 μg / mL were poured into the root zone of the potted plants. At the same time, 10 μg / mL abamectin was used as a positive control and water was used as a blank control. Each treatment was replicated 5 times. After 60 days, the number of root knots formed on the pepper roots was counted and the control effect was calculated (Xinjiang Agricultural Science and Technology,2022,(02):42-44.). The calculation formula is: control effect (%) = [(disease index of control area - disease index of treatment area) / disease index of control area] × 100%.

[0089] Table 6 shows the control efficacy of compound 1 against southern root-knot nematodes in potted plants. Figure 2 )

[0090]

Claims

1. A compound or a pesticidally acceptable salt thereof, characterized by The compound has a structure as shown in compounds 1-3 below: 、 、 。 2. A process for the preparation of the compounds 1, 2 and / or 3 according to claim 1, characterized in that The method comprises the following steps: (1) preparing a seed culture medium, inoculating the marine fungus Eupenicillium sp. HJ002 strain into the seed culture medium, culturing at 26-28°C for 3-4 days to obtain a seed culture solution; (2) inoculating the seed culture solution obtained in step (1) into a fermentation culture medium, and culturing at room temperature for 28-30 days to obtain a fermentation product; (3) extracting the fermentation product obtained in step (2) with ethyl acetate, extracting 2-4 times, and then concentrating the ethyl acetate phase under reduced pressure to obtain an extract; (4) subjecting the extract obtained in step (3) to reduced-pressure silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate as the eluent, and the elution gradient is 100:0, 90:10, 80:20, 70:30, 60:40, 50:50, 40:60, 30:70, 20:80, 10:90 and 0:100, and two column volumes are collected for each gradient, and the eluate is divided into six components according to the polarity, wherein the eluate obtained in the gradient of 100:0-90:10 is component 1, the eluate obtained in the gradient of 80:20-70:30 is component 2, the eluate obtained in the gradient of 60:40-50:50 is component 3, the eluate obtained in the gradient of 40:60-30:70 is component 4, the eluate obtained in the gradient of 20:80-10:90 is component 5, and the eluate obtained in the gradient of 0:100 is component 6, wherein component 3 is first subjected to normal-phase silica gel column chromatography, the eluent is a mixed solvent of petroleum ether: ethyl acetate = 20:1-10:1, 2-5 column volumes of eluate are collected, and then high-performance liquid chromatography (HPLC) preparation is performed, the chromatographic column is Waters C18, 9.4×250 mm, 7 μm, the flow rate is 2 mL / min, and the mobile phase is MeOH:H2O = 10:90-20:80, to obtain compounds 1, 2 and / or 3.

3. Use of the marine fungus Eupenicillium sp. HJ002 in the preparation of the compounds 1, 2 and / or 3 according to claim 1; the preservation number of the marine fungus Eupenicillium sp. HJ002 is CGMCC No. 13373.

4. Use of the compounds 1, 2 and / or 3 according to claim 1 in the prevention and treatment of agricultural pests and diseases.

5. Use according to claim 4, characterized in that The agricultural pests and diseases are caused by one or more of the following: Colletotrichum musae, Botrytis cinerea, Sclerotinia sclerotiorum and Meloidogyne incognita.

6. Use of the compounds 1, 2 and / or 3 according to claim 1 in the preparation of an antioxidant.

7. A pesticidal composition, characterized by The pesticide composition comprises the compounds 1, 2 and / or 3 according to claim 1 or a pharmaceutically acceptable salt thereof as an effective ingredient.

8. The pesticidal composition according to claim 7, characterized in that The pesticide composition can further comprise a pharmaceutically acceptable adjuvant.

9. The pesticidal composition according to any one of claims 7-8, characterized in that The pesticide composition can further comprise other insecticidal and fungicidal active ingredients.

10. An antioxidant agent characterized in that The antioxidant comprises the compounds 1, 2 and / or 3 according to claim 1 or a pharmaceutically acceptable salt thereof as an effective ingredient.

11. The antioxidant of claim 10, wherein The antioxidant can further comprise other antioxidants.

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