Insecticidal and bactericidal compound derived from marine fungi and preparation method of insecticidal and bactericidal compound

Abstract

The invention belongs to the field of secondary metabolites of marine fungi, and particularly relates to an insecticidal and bactericidal compound derived from marine fungi and a preparation method thereof, and the insecticidal and bactericidal compound has a structure as shown in the following compounds 1-3: # imgabs0 #.

Description

Technical Field

[0001] The invention belongs to the field of marine fungus secondary metabolites, and specifically relates to an insecticide and fungicide compound derived from marine fungi and a preparation method thereof. Background Art

[0002] Mangrove plants grow in tropical and subtropical intertidal zones. Their living environment is characterized by high pressure, high salt, and low oxygen, which makes their endophytic fungi have unique metabolic pathways, and thus have the ability to produce compounds with novel structures and diverse biological activities. Their metabolites have insecticidal, bactericidal, antioxidant and other medicinal values, and are potential resources for the development of microbial drugs. Therefore, mangrove endophytic fungi will become one of the important resources for the research and development of biological pesticides. The applicant previously obtained a series of anti-tumor active indole diterpenoid compounds from the marine fungus Eupenicillium sp.HJ002 (Chinese patent application numbers: 201710416276.1 and 201710417257.0), and further studied the marine fungus Eupenicillium sp.HJ002 to obtain a series of insecticidal and bactericidal compounds. Summary of the invention

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

[0004]

[0005] Another embodiment of the present invention provides a method for preparing the above-mentioned compounds 1, 2 and / or 3, characterized in that it comprises the following steps:

[0006] (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;

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

[0008] (3) extracting the fermented product obtained in step (2) with ethyl acetate for 2 to 4 times, combining the ethyl acetate phases and concentrating under reduced pressure to obtain an extract;

[0009] (4) The extract obtained in step (3) was subjected to vacuum silica gel column chromatography, and petroleum ether-ethyl acetate was used as the eluent for gradient elution. 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, respectively. Two column volumes were collected for each gradient, and the components were divided into 6 components according to their polarity. Component 1 was obtained by eluting with a gradient of 100:0 to 90:10, and component 2 was obtained by eluting with a gradient of 80:20 to 70:3. 0 to obtain component 2, eluted at a gradient of 60:40 to 50:50 to obtain component 3, eluted at a gradient of 40:60 to 30:70 to obtain component 4, eluted at a gradient of 20:80 to 10:90 to obtain component 5, and eluted at a gradient of 0:100 to obtain component 6, wherein component 3 was first chromatographed on a normal phase silica gel column, the eluent being a mixed solvent of petroleum ether: ethyl acetate = 20:1-10:1, eluted for 2-5 column volumes, concentrated under reduced pressure, and then prepared by high performance liquid chromatography HPLC, the chromatographic column being Waters C18, 9.4×250mm, 7μm, the flow rate being 2mL / min, and the mobile phase being MeOH:H2O = 10:90-20:80, to obtain compounds 1, 2 and / or 3.

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

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

[0012] Another embodiment of the present invention provides the use of the above compounds 1, 2 and / or 3 in preventing and controlling agricultural pests and diseases. The agricultural pests and diseases are preferably caused by one or more of banana anthracnose, tomato gray mold, rapeseed sclerotinia, and southern root-knot nematodes.

[0013] Another embodiment of the present invention provides 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 the above-mentioned compounds 1, 2 and / or 3 or their pesticide-acceptable salts as active ingredients. The pesticide composition may also include pesticide-acceptable adjuvants. The pesticide composition may also include other insecticide and fungicide active ingredients.

[0015] Another embodiment of the present invention provides an antioxidant, characterized in that the antioxidant contains the above-mentioned compound 1, 2 and / or 3 or a pharmaceutically acceptable salt thereof as an effective ingredient. The antioxidant may also include other antioxidants.

[0016] The marine fungus Eupenicillium sp.HJ002 involved in the present invention is a known strain, and its strain preservation information is as follows: name of the depository: General Microbiology Center of China Microbiological Culture Collection Administration; address of the depository: Institute of Microbiology, Chinese Academy of Sciences, No. 3, Yard 1, Beichen West Road, Chaoyang District, Beijing; date of deposit: December 21, 2016; deposit number: CGMCC No.13373; classification name: Eupenicillium sp.; disclosed in the applicant's previous Chinese patent application numbers: 201710416276.1 and 201710417257.0. BRIEF DESCRIPTION OF THE DRAWINGS

[0017] Figure 1 It is the antifungal activity bacterial plate diagram of compound 1, note: XT: banana anthracnose pathogen, the test concentration is 10-50μg / mL; tomato gray mold pathogen: the test concentration is 20-60μg / mL; YC: rapeseed sclerotinia pathogen, the test concentration is 10-50μg / mL; CK is the blank control.

[0018] Figure 2 This is a graph showing the protective effect of compound 1 on southern root-knot nematodes in potted plants.

[0019] Figure 3 It is compound 1-3 1 H- 1 H COSY and HMBC correlation signals.

[0020] Figure 4 It is the NOESY spectrum of compound 1-2.

[0021] Figure 5 is the experimental ECD spectrum of compound 1-2.

[0022] Figure 6 is compound 1 1 H NMR spectra.

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

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

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

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

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

[0028] Fig.12 It is the NOESY diagram of compound 1.

[0029] Fig.13 is the HR-ESI-MS spectrum of compound 1.

[0030] Fig.14 is compound 1 1 H NMR spectra.

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

[0032] Fig.16 This is the 135°-DEPT diagram of compound 2.

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

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

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

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

[0037] Fig.21 is the HR-ESI-MS spectrum of compound 2.

[0038] Fig. 22 is compound 3 1 H NMR spectra.

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

[0040] Fig.24 This is the 135°-DEPT diagram of compound 3.

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

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

[0043] Fig. 27 is the HR-ESI-MS spectrum of compound 3. DETAILED DESCRIPTION

[0044] In order to facilitate further understanding of the present invention, the following examples are provided to illustrate it in more detail. However, these examples are only for better understanding of the invention and are not intended to limit the scope or implementation principles of the present invention. The implementation methods of the present invention are not limited to the following contents.

[0045] Example 1

[0046] (1) The fungus Eupenicillium sp. HJ002 strain was inoculated into a potato glucose water medium (PDB medium), each 1L conical flask was filled with 350mL of PDB medium, and a total of 5 bottles of seed liquid were fermented at 28°C for 3 days to obtain a seed culture solution;

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

[0048] (3) extracting the fermented product obtained in step (2) with an appropriate amount of ethyl acetate three times; combining the ethyl acetate phases and concentrating under reduced pressure to obtain an extract.

[0049] (4) The extract obtained in step (3) was subjected to vacuum silica gel column chromatography, and petroleum ether-ethyl acetate was used as the eluent for gradient elution. 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, respectively. Two column volumes were collected for each gradient, and the components were divided into 6 components according to their polarity. Component 1 was obtained by eluting with a gradient of 100:0 to 90:10, and component 2 was obtained by eluting with a gradient of 80:20 to 70:3. 0 to obtain component 2, eluted with a gradient of 60:40-50:50 to obtain component 3, eluted with a gradient of 40:60-30:70 to obtain component 4, eluted with a gradient of 20:80-10:90 to obtain component 5, and eluted with a gradient of 0:100 to obtain component 6, wherein component 3 was first chromatographed on a normal phase silica gel column, the eluent was a mixed solvent of petroleum ether: ethyl acetate = 20:1-10:1, eluted for 2-5 column volumes, concentrated under reduced pressure, and then prepared by high performance liquid chromatography HPLC, the chromatographic column was Waters C18, 9.4×250mm, 7μm, the flow rate was 2mL / min, and the mobile phase was MeOH:H2O = 10:90-20:80, to obtain compounds 1 (60.3mg), 2 (7.4mg) and / or 3 (5.6mg).

[0050]

[0051] The structural confirmation data of compound 1-3 are as follows:

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

[0053]

[0054]

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

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

[0057]

[0058] a DMSO-d6, b CDCl3

[0059] Compound 1: White powder. According to high-resolution mass spectrometry HR-ESI-MS, a quasi-molecular ion peak [M+Na] was given at m / z 245.0781. +Combining the hydrogen and carbon spectrum data, it is inferred that the molecular formula of the compound is C 12 H 14 O4, its unsaturation is 6. 1 The H-NMR spectrum (Table 1) indicates that the compound has one olefinic proton signal [δ H 6.08(s)], 1 methine hydrogen signal δ H 3.03 (m), 1 oxymethylene 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)], and two methyl signals appeared in the high field region [δ H 2.17(s) and δ H 1.44(s)]; combined 13 C-NMR (Table 2) and DEPT135° spectrum show that the compound has 12 resonant carbon signals, including one ester carbonyl carbon signal δ C 161.1, 4 olefinic carbon signals δ C (165.9, 162.5, 99.5 and 98.9), 1 quaternary carbon signal δ C (99.9), 1 oxymethylene carbon signal δ C (59.2), 2 methylene carbon signals δ C (33.5,27.4), 1 methine 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 ) gives the CH2(7)-CH(6)-CH2(9)-CH2(10) linker fragment. Combined with the HMBC spectrum, we can get the correlations of 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, respectively. Combined with the NOESY spectrum ( Figure 4) It can be seen that H-6 is related to H-12, thus confirming that the hydrogen atoms of H-6 and H-12 are oriented in the same direction. The planar configuration and relative configuration of the compound were determined based on the above 1D / 2D NMR data. In order to determine the absolute configuration of compound 1, the theoretical ECD spectra of the two possible stereoisomers of 6R, 8R and 6S, 8S were calculated by TDDFT. The results showed that the calculated ECD curves of 6R, 8R-isomers were 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: Yellow oil. The molecular formula of the compound was inferred to be C from high-resolution mass spectrometry HR-ESI-MS and 1D and 2D NMR spectra. 13 H 16 O4, unsaturation is 6, compared with the 1D NMR data of compound 1 (Table 1 and Table 2), it is found that the carbon spectrum data are similar and suspected to be a series of compounds, and have the same 6 / 6 / 6 heterocyclic tricyclic skeleton; the main difference is that the [δ H 1.86(s),δ C 9.1(CH3)] has a methyl group, [δ H 6.08(s)], there is no aromatic proton signal. According to the relevant signals in the HMBC spectrum, it is concluded that there are relevant signals from H-13 to C-3 / C-4 / C-5 ( Figure 3 ), which indicates that a methyl group is connected to C-4. Combined with the NOESY spectrum, we can see that H-6 and H-12 have related signals, which further proves that the relative configuration is consistent with compound 1. According to the CD test data ( Figure 5) shows that a negative Cotton effect is observed at 282 nm, and the absolute configurations of C-6 and C-12 are calculated by ECD ( Figure 5 ) was determined to be 6S, 8S. Thus, 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: Yellow oil. According to the molecular ion characteristics of high-resolution mass spectrometry HR-ESI-MS, a quasi-molecular ion peak [M+K] was given at m / z 285.0696. + , the molecular formula of the compound is inferred to be C 13 H 14 N2O3, its unsaturation is 8. 1 The H-NMR spectrum (Table 1) shows that the 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 There are two methyl hydrogen signals [2.32(s)and 2.16(s)] at (1.0-2.5); combined 13 C-NMR (Table 2) and DEPT135° spectrum show that the compound has 13 resonant carbon signals, including one ketocarboxyl carbon signal δ C 181.9, 8 olefinic carbon signals δ C (168.5, 167.6, 160.7, 154.9, 126.4, 113.5, 102.3 and 100.0), 1 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). According to 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, H-13 to C-9 / C-10 are correlated, respectively. Combined with the HR-ESI-MS data, it is determined that the 2,4-dihydroxy-5-methylpyridine fragment passes through a methylene [δ C 20.0 and δ H 3.40(s)] linked to the 2-methyl-4-pyridone moiety ( Figure 3 ), the planar structure of the compound was determined based on the above 1D / 2D NMR data. Therefore, the structure of compound 3 was determined to be a new α-pyridone derivative and 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) Test instruments and materials: total antioxidant capacity test kit, PBS buffer solution, 96-well plate, microplate reader, EP tube and pipette, etc.

[0068] (2) The working stock solution in step (1) was diluted with PBS buffer solution to form ABTS working solution (diluted 35-50 times), and then the absorbance range was tested at 734 and 405 nm using an ELISA reader 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 (about 1.4)

[0070] (3) Antioxidant capacity test:

[0071] The antioxidant activity of compounds 1-3 was tested using a total antioxidant capacity detection kit. PBS was used as the buffer solution, and the sample concentrations were configured to be 0.75, 0.5, 0.25, 0.125, and 0.0625 mg / mL in a total of 5 gradients. The test required the addition of 200 μL ABTS working solution, 10 μL of the sample to be tested (experimental group), 10 μL PBS (blank group), and 10 μL Trolox (positive control group) to a 96-well plate, and the test was repeated 3 times in parallel. After standing for 5-7 minutes, the absorbance value at a wavelength of 734 or 405 nm was measured. The inhibition rate of the test sample was calculated according to the following formula: Inhibition rate (%) = [(A blank -A sample ) / A blank ]×100%, and the IC was calculated by GraphPad Prism 9 software. 50 value.

[0072] (4) Experimental results:

[0073] Table 3 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, 0.5 cm diameter hole puncher, ruler, sealing film, tweezers, sterilizing pot, PDA culture medium, oxadiazine, analytical grade methanol, banana anthracnose pathogen (Calletotrichummusae), tomato gray mold pathogen (Botrytis cinerea) and rapeseed sclerotinia pathogen (Sclerotiniasclerotiorum).

[0077] (2) The mycelium growth rate inhibition method (Journal of Agricultural and Food Chemistry. 2024, 72(10): 5258-5268.) was used to detect the in vitro mycelium inhibition rate. 1 mg of the sample to be tested was completely dissolved in a small amount of methanol, and the sample to be tested was mixed with 50 mL of PDA culture medium to a final concentration of 10, 15, 20, 30, 40, 50, 60 μg / mL, and evenly poured into a sterilized plate; then the activated plant pathogens were punched into a cake with a sterilized puncher (diameter 0.5 cm), and the cake with mycelium was inoculated into the center of a sterile PDA plate. An equal volume of methanol without compounds was used as a blank control, and oxadiazine was used as a positive control. The treatment and control were placed in an incubator at (27±1)℃ in the dark for 2-6 days, and the experiment was terminated when the pathogens in the control group grew to a colony diameter of more than 5.5 cm. All treatments were repeated 3 times. The diameter of the inhibition zone (cm) was measured by the cross method using a standard ruler, and the average value was taken. The mycelium growth inhibition rate = (the colony diameter of the control group - the colony diameter of the treatment group) / (the colony diameter of the control group - 0.5) × 100%; and the EC was calculated using SPSS software. 50 Values ​​and independent regression equations.

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

[0079] Table 4 Results of the anti-plant pathogenic activity of compound 1

[0080]

[0081] Example 4 Anti-southern root-knot nematode activity test:

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

[0083] (2) The insecticidal activity of compounds 1-3 against southern root-knot nematodes was determined by the poisoning method in the literature (Journal of Agricultural and Food Chemistry. 2023, 71(36): 13209-13219.). The initial screening concentration of the sample test 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 the positive control and clean water was used as the blank control. Each agent was set up for 3 parallel and 3 repeated tests. The death of nematodes was observed and counted 24, 48, and 72 hours after application, and the corrected mortality of nematodes was calculated. The formula is as follows:

[0084] Corrected mortality rate (%) = mortality rate - blank mortality rate / (1 - blank mortality rate) × 100%

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

[0086]

[0087] Example 5 Potted plant experiment on anti-southern root-knot nematode activity:

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

[0089] Table 6 Effect of compound 1 on the control of southern root-knot nematode potted plants ( Figure 2 )

[0090]

Claims

1. A compound or a pesticide acceptable salt thereof, characterized in that The compound has the structure shown in the following compound 1-3:

2. A method for preparing compound 1, 2 and / or 3 according to claim 1, characterized in that The steps include: (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 medium, and culturing at room temperature for 28 to 30 days to obtain a fermentation product; (3) extracting the fermented product obtained in step (2) with ethyl acetate for 2 to 4 times, combining the ethyl acetate phases and concentrating under reduced pressure to obtain an extract; (4) The extract obtained in step (3) was subjected to vacuum silica gel column chromatography, and petroleum ether-ethyl acetate was used as the eluent for gradient elution. 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, respectively. Two column volumes were collected for each gradient, and the components were divided into 6 components according to their polarity. Component 1 was obtained by eluting with a gradient of 100:0 to 90:10, and component 2 was obtained by eluting with a gradient of 80:20 to 70:

3. 0 to obtain component 2, eluted at a gradient of 60:40 to 50:50 to obtain component 3, eluted at a gradient of 40:60 to 30:70 to obtain component 4, eluted at a gradient of 20:80 to 10:90 to obtain component 5, and eluted at a gradient of 0:100 to obtain component 6, wherein component 3 was first chromatographed on a normal phase silica gel column, the eluent being a mixed solvent of petroleum ether: ethyl acetate = 20:1-10:1, eluted for 2-5 column volumes, concentrated under reduced pressure, and then prepared by high performance liquid chromatography HPLC, the chromatographic column being Waters C18, 9.4×250mm, 7μm, the flow rate being 2mL / min, and the mobile phase being MeOH:H2O = 10:90-20:80, to obtain compounds 1, 2 and / or 3.

3. Use of marine fungus Eupenicillium sp. HJ002 in the preparation of 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 preventing and controlling agricultural pests and diseases.

5. The use according to claim 4, characterized in that The agricultural pests and diseases are preferably caused by one or more of banana anthracnose, tomato gray mold, rapeseed sclerotinia, and southern root-knot nematodes.

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

7. A pesticide composition, characterized in that The pesticide composition contains the compound 1, 2 and / or 3 as claimed in claim 1 or its pesticide acceptable salt as an active ingredient.

8. The pesticide composition according to claim 7, characterized in that The pesticide composition may further include pesticide-acceptable adjuvants.

9. The pesticide composition according to any one of claims 7 to 8, characterized in that The pesticide composition may also include other insecticide and fungicide active ingredients.

10. An antioxidant, characterized in that The antioxidant comprises the compound 1, 2 and / or 3 or a pharmaceutically acceptable salt thereof as claimed in claim 1 as an effective ingredient. The antioxidant may also include other antioxidants.

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