CN107722032B - Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof - Google Patents
Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof Download PDFInfo
- Publication number
- CN107722032B CN107722032B CN201710932387.8A CN201710932387A CN107722032B CN 107722032 B CN107722032 B CN 107722032B CN 201710932387 A CN201710932387 A CN 201710932387A CN 107722032 B CN107722032 B CN 107722032B
- Authority
- CN
- China
- Prior art keywords
- anhydride compound
- prodenia litura
- poisoning
- ethyl acetate
- acid anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
Abstract
The invention discloses an anhydride compound with a prodenia litura poisoning activity, which has a structure shown in the following formula (I):
the compound has good prodenia litura poisoning activity. The invention also discloses a preparation method of the anhydride compound and application of the anhydride compound in preparing a poisoning agent with a prodenia litura poisoning effect.
Description
Technical Field
The invention belongs to the technical field of anhydride compounds, and particularly relates to an anhydride compound with prodenia litura poisoning activity, and a preparation method and application thereof.
Background
Spodoptera litura Fabricius belongs to the family of Lepidoptera (Lepidotera) Noctuidae (Noctuidae), also known as Neuroptera litura, commonly known as nocturnal worms, black-headed worms and the like, is a world-wide distributed omnivorous and binge crop pest and is distributed in tropical and subtropical regions of Asia, European mediterranean regions and Africa. The insect pests occur in various parts of China, particularly in warm areas of the south of Huaihe river, and in the middle and lower reaches of Yangtze river and in the south of China, the insect pests are more likely to occur in the north. The prodenia litura is not only widely distributed in regions, but also widely harmful to hosts, and reportedly, the prodenia litura can harm host plants of 389 (including varieties) of 109 families, and the prodenia litura can harm cruciferous vegetables such as Chinese cabbage, radish, mustard and the like, and also can harm spinach, leek, shallot and the like, and relates to ferns, gymnosperms, dicotyledons and monocotyledons. In the north China, 4-5 generations in 1 year and 6-9 generations in the south China, the generations are overlapped seriously, and the diapause characteristic is not generated. The female adults can lay eggs for 8-17 eggs in a life, about 1000-2000 eggs, and 3000 eggs at most, and as long as the environmental conditions are suitable, the population density can be rapidly increased, and disasters often occur. In recent years, the outbreak frequency of prodenia litura is obviously increased, the area is enlarged year by year, and the damage is becoming more and more serious. Tomatoes, hot peppers, eggplants, watermelons, bitter gourds, cowpeas, cabbages and the like planted in the Hainan island in a large scale are all harmed by the insects, the planting production and the economic benefit of crops are seriously influenced, and the harm is great.
The occurrence rule of prodenia litura is closely related to temperature, things and the like, and compared with other pests, the prodenia litura prefers high temperature and can grow and develop rapidly at the temperature of 28-30 ℃, so summer is often the high-incidence season of the prodenia litura and is also the key period for preventing and controlling the prodenia litura. On the other hand, the food of prodenia litura, namely the host thereof, also has great influence on the generation of the prodenia litura, the larvae of the prodenia litura have wide feeding habits, a plurality of crops and plants are difficult to escape from the harm of the prodenia litura, but the prodenia litura also has certain preference for the food, and different foods have great influence on the growth and development of the prodenia litura. The spodoptera litura larvae have large food intake, and when the spodoptera litura larvae occur in certain places, the spodoptera litura larvae often cause serious yield reduction of crops and even no grain harvest.
In actual production, chemical control becomes an essential measure for controlling prodenia litura. Because of frequent and irregular use of chemical pesticides, a large number of natural enemies in farmlands are killed and killed, and the control effect of natural control factors in a farmland ecosystem on prodenia litura is weakened, so that the prodenia litura is erupted in successive years. Chemical pesticides are generally preferred for the control of prodenia litura. The previous researches show that the carbaryl not only has higher permeability and insecticidal activity on prodenia litura larvae, but also can reduce the reproductive capacity of prodenia litura adults. Meanwhile, researches find that part of pyrethroid pesticides (such as fenvalerate and deltamethrin) have good control effect on prodenia litura larvae. Then, the pyrethroid pesticide and the compound chemical pesticide mixed with the pyrethroid pesticide have continuous literature reports on the field pesticide effect test of spodoptera litura larvae. However, people soon find that prodenia litura has different degrees of resistance to various chemical pesticides and the control effect is reduced. Drug resistance is one of the important reasons for the rampant of the pests and is also a key factor influencing the use effect of the pesticide. In India, in 1995, the resistance of prodenia litura to pyrethrum, endosulfan, lindane, monocrotophos, fenitrothion, dimethoate, malathion, fenthion, methyl parathion, cypermethrin, fenvalerate and deltamethrin was significantly increased compared to 1961, 1970 and 1987, respectively. The prodenia litura is also reported to generate resistance to pyrethroid and organophosphorus pesticides in China. Abamectin, chlorpyrifos, beta-cypermethrin and indoxacarb have been used in the fields for a long time in Hainan island with very high frequency, and thus have developed serious drug resistance. Meanwhile, the resistance of the spodoptera litura larvae eating different host plants to pesticides is found to be different. The problems caused by the use of a large amount of pesticides are getting worse, so that people are forced to explore a new way for controlling the environmental-friendly and harmonious prodenia litura.
For a long time, when preventing and treating agricultural diseases and insect pests, a large amount of high-efficiency broad-spectrum chemical pesticide is used, and a plurality of beneficial natural enemies are eliminated while the diseases and insect pests are killed, so that the ecological balance in the nature is seriously damaged. Moreover, because of continuous use in one area, pathogenic microorganisms gradually generate drug resistance, so that the use of chemical pesticides can not achieve the expected effect, but can pollute agricultural products and the environment, and further harm human health. At present, the idea of environmental protection and agricultural sustainable development is generally accepted by people, other alternative natural biogenic product pesticides which have small toxic and side effects, are safe and effective and are compatible with the environment are searched for to prevent and treat crop diseases, and the production of pollution-free products and green food is ensured.
In recent years, people pay general attention to screening and searching for insecticidal medicaments from natural products, and the insecticidal medicaments are one of important ways for finding new biological pesticides. Metabolites produced by microorganisms have been developed rapidly in recent years as pesticides, i.e., agricultural antibiotics, have become one of the main sources of microbial pesticides, and can be used for biological control or provide a new source of environmentally friendly pesticides. The research on secondary metabolites of microorganisms with agricultural pest and disease resistance activity opens up a new way for researching and developing biogenic natural product pesticides, and the method has great application value and development potential.
Disclosure of Invention
The invention aims to provide an anhydride compound with a prodenia litura poisoning activity, and the compound has a good prodenia litura poisoning activity.
The invention also aims to provide a preparation method of the anhydride compound with the prodenia litura poisoning activity, and the preparation method is simple in process and low in cost.
The third purpose of the invention is to provide the application of the anhydride compound with the prodenia litura poisoning activity in preparing the poisoning agent with the prodenia litura poisoning effect.
The first purpose of the invention is realized by the following technical scheme: an acid anhydride compound having a prodenia litura poisoning activity, which has a structure as in the following formula (I):
the structural formula of the compound is C18H20O6Actually measured scoreThe quantum number is 331.1184([ M-H)]-Molecular ion peak of [ M-H ]]-Theoretical molecular weight 331.1182).
The acid anhydride compound is produced by fermentation of aspergillus fumigatus (Aspergillus fumigatus) JRJ111048 with the preservation number of CGMCC No. 14155.
Aspergillus fumigatus (Aspergillus fumigatus) JRJ111048 with the preservation number of CGMCC No.14155 is obtained by culturing and screening Aspergillus fumigatus in leaves of Haliotis acuminata Hance of Hainan, is separated from leaves of Haliotis acuminata Hance of Hongkong mountain mangrove forest of east village of Hainan, China, and is identified as Aspergillus fumigatus (Aspergillus fumigatus) through molecular biological research.
The taxonomic nomenclature of this aspergillus fumigatus strain JRJ 111048: aspergillus fumigatus (Aspergillus fumigatus), depository: china general microbiological culture Collection center (CGMCC for short, address: No. 3 Xilu-Beijing university of Chaoyang district, No.1 Beichen, institute of microbiology, China academy of sciences), and the preservation address: beijing, China, preservation date: 9/4/2017, and the accession number is: CGMCC number 14155.
The second purpose of the invention is realized by the following technical scheme: the preparation method of the anhydride compound with the prodenia litura poisoning activity comprises the following steps:
(1) activating Aspergillus fumigatus JRJ111048 by slant, inoculating in ME culture medium, and culturing at 26-30 deg.C for 180-250 r.min-1Carrying out shake culture for 3-5 days, inoculating into an ME culture medium according to an inoculum size (volume percentage content) of 3-10%, and carrying out inoculation at 26-30 ℃ for 180-250 r.min-1Carrying out shake culture for 12-15 d to obtain fermentation liquor;
(2) extracting the fermentation liquor by using ethyl acetate with the same volume, and concentrating an ethyl acetate extract under reduced pressure until the ethyl acetate extract is dry to obtain a crude extract;
(3) suspending the crude extract with distilled water, sequentially extracting with chloroform and ethyl acetate of equal volume to obtain a chloroform extraction layer A, an ethyl acetate extraction layer B and a water layer part C, then carrying out silica gel open column chromatography on the ethyl acetate extraction layer B, carrying out gradient elution with chloroform-methanol at volume ratios of 100:0, 100:1, 100:2, 100:4, 100:8 and 0:100 to obtain sub-fractions B1, B2, B3, B4, B5 and B6, and carrying out ODS column chromatography and Sephadex-LH20 on the sub-fraction B2 for separation to obtain the anhydride compound with the spodoptera litura poisoning activity.
In the preparation method of the anhydride compound with the prodenia litura poisoning activity:
the ME culture medium 1L in the step (1) contains the following components by mass: 8-10 g of malt extract, 16-20 g of sucrose and 2-4 g of peptone, wherein the pH value of the ME culture medium is 7.0-7.2.
In the step (2), the fermentation liquor is extracted for 2-3 times by using ethyl acetate with the same volume, and the temperature of reduced pressure concentration is 40-60 ℃.
The third purpose of the invention is realized by the following technical scheme: the acid anhydride compound is applied to preparing a poisoning agent with a prodenia litura poisoning effect.
Preferably, the poisoning agent is applied to crops of cotton, tobacco, soybean, taro, peanut, sesame, lotus root, Chinese cabbage, radish, mustard, spinach, leek or shallot for preventing and treating prodenia litura.
Compared with the prior art, the invention has the following advantages:
(1) the anhydride compound with the structure shown as the formula (I) is not separated from microorganisms, and the structure is not reported, so that the anhydride compound is a new-structure compound;
(2) a biological activity test experiment shows that the acid anhydride compound with the structure shown in the formula (I) has strong prodenia litura poisoning activity, and the compound can be used as a prodenia litura poisoning agent and can be used as a biological pesticide for preventing and treating prodenia litura from damaging crops such as cotton, tobacco, soybean, taro, peanut, sesame, lotus root, Chinese cabbage, radish, mustard, spinach, leek, shallot and the like.
Drawings
FIG. 1 is a high resolution mass spectrum in example 4;
FIG. 2 is a drawing obtained in example 41H, one-dimensional nuclear magnetic resonance spectrum;
FIG. 3 is an embodiment4 in13C one-dimensional nuclear magnetic resonance spectrum;
FIG. 4 is the HSQC two-dimensional NMR spectrum of example 4;
FIG. 5 is the HMBC two-dimensional nuclear magnetic resonance spectrum of example 4;
FIG. 6 shows the results obtained in example 41H-1H COSY two-dimensional nuclear magnetic resonance spectrum;
FIG. 7 is the ROESY two-dimensional NMR spectrum in example 4;
Detailed Description
In the following examples, the mass spectrometers are Bruker amaZon SL (low resolution) and Agilent 6210 TOF LC-MS (high resolution) mass spectrometers. The superconducting nuclear magnetic resonance instrument is Bruker AVIII-500. Silica gel GF254 and column chromatography silica gel (200-300 mesh) for thin layer chromatography are both products of Qingdao ocean chemical plant. The reversed phase ODS packing and Sephadex LH-20 are both products from Merck, USA. The water is double distilled water, and other reagents are analytically pure. In the biological activity test, the insecticidal activity test model for spodoptera litura was referred to Medicinal Chemistry Research,2014,23(7):3347-3352(CA-4, artificial cis-stine compound with a porous insecticidal activity, Xiu-QingLv, Gang Feng, Ying-Qian Liu, Xiang Nan, Liu Yang). The positive insecticide azadirachtin was purchased from Haikou Shengjing technology Ltd.
Example 1
A fungal strain JRJ111048 was isolated from leaves of haloperi conifer (Haliotis acridicola) of the mangrove plant collected from the mangrove forest of east village, Hainan, China, and was identified by molecular biology studies as Aspergillus fumigatus, the strain being classified under the name: aspergillus fumigatus (Aspergillus fumigatus), depository: china general microbiological culture Collection center (CGMCC for short, address: No. 3 Xilu-Beijing university of Chaoyang district, No.1 Beichen, institute of microbiology, China academy of sciences), and the preservation address: beijing, China, preservation date: 9/4/2017, and the accession number is: CGMCC number 14155.
The GenBank accession number of the 18S rRNA gene sequence of the strain is MF817615, and the sequence is as follows:
example 2 method for pretreating large-scale fermentation and fermentation sample of JRJ111048 strain
Activating Aspergillus fumigatus JRJ111048 by slant, inoculating into ME culture medium, inoculating at 28 deg.C for 210r min-1Shaking for 3d, inoculating into 20L ME culture medium at 28 deg.C and 220r min-1And carrying out shake culture for 13d to obtain a fermentation liquor. The fermentation broth was extracted with an equal volume of ethyl acetate (20L), extraction was repeated 3 times, the ethyl acetate extracts were combined and concentrated to dryness at 60 ℃ under reduced pressure to give a crude extract. The ME culture medium comprises the following components in percentage by weight and volume: malt extract 10g/L, sucrose 20g/L, peptone 2g/L, pH value adjusted to 7.0.
Isolation of the Compound of example 3
The crude extract obtained in example 2 was suspended in distilled water, followed by extraction with equal volumes of chloroform and ethyl acetate in this order to obtain a chloroform extraction layer (A), an ethyl acetate extraction layer (B) and an aqueous layer fraction (C). Subjecting the ethyl acetate layer (B) to silica gel column chromatography, and performing gradient elution with chloroform-methanol at volume ratios of 100:0, 100:1, 100:2, 100:4, 100:8, and 0:100 to obtain 6 sub-fractions of B1, B2, B3, B4, B5, and B6. ODS column chromatography and Sephadex-LH20 column chromatography were performed on fraction B2(833.5mg) to give anhydride compound 1(9.6 mg).
EXAMPLE 4 structural characterization of the Compounds
The structure of the compound is determined by various spectral means such as high-resolution mass spectrum (shown in figure 1) and nuclear magnetic resonance (including one-dimensional and two-dimensional NMR experiments) (shown in figures 2-7), and the compound is an unreported anhydride compound with a new structure and is named as glaucinic acid.
It is composed of1H、13The C NMR data are shown in Table 1 below:
TABLE 1 NMR data and assignment of Compound 1 (CDCl)3For testing the solvent, the delta unit is ppm)
The structural formula is as follows:
example 5 Twill Capricornus spodoptera killing Activity test of extract samples, fraction samples and Compound 1
5.1 test organisms: the prodenia litura eggs are collected from lotus leaf which is not applied with medicine in Guilin ocean Fuyuncan in the Milan region of Hainan Haikou Longhua, and are bred for a plurality of generations indoors, and during the test, the initially hatched larvae which are just hatched for 2 hours in the same egg mass are selected for the test.
5.2 test methods
The insecticidal activity adopts a feed mixed toxicity method. A test sample (crude extract in example 2, fraction B2 in example 3, compound 1) was prepared to be 1mg/mL with acetone, a small amount of DMSO (content below 1%) was added to individual insoluble samples to prepare a spodoptera litura semi-artificial feed, and 1mL of the semi-artificial feed was added to each well of a 12-well plate while hot. After the feed is solidified, 20 mu L of sample to be detected is added into each hole, 10 holes are added into each sample, and the process is repeated for 3 times. After the solvent is volatilized, 1 prodenia litura hatched for 2 hours is inoculated into each hole and is hatched for the first time, the prodenia litura hatched for the first time is placed into an insect breeding chamber with the temperature of 25 +/-1 ℃ and the humidity of 80 percent for breeding, acetone (acetone and cosolvent) is used as a solvent contrast, azadirachtin is used as a medicament contrast, the death conditions of the test insects are checked at 7d, 10d, 14d and 20d after inoculation respectively, and the death rate is calculated.
5.3 insecticidal Activity results
Fraction B2 and compound 1 gave very strong poisoning against spodoptera litura larvae, slightly less than the control agent azadirachtin. Mortality rates tended to increase with treatment time, and specific activity results are shown in table 2 below.
The observation of the toxicity symptoms shows that the fraction B2 and the compound 1 have certain inhibition effect on the growth and development of prodenia litura, which is specifically shown in that the weight of treated test insects is slowly increased, and the individuals are small. In the pre-pupation stage, the control test insects can pupate normally, and the pupae are full. After the treated test insects enter a prepupation period, the epidermis cannot be sloughed off so as to form mature larvae; only part of epidermis of individual larva can be sloughed off to form half larva and half pupa state; compared with the control, the test pupa capable of pupating normally has smaller pupa body and malformation of individual pupa. When the adult stage is reached, the control survival test insects can normally emerge, the emergence rate of the treated group test insects is low, the moth bodies are small, and part of the imagoes can not normally break pupae to emerge so as to form deformed imagoes of semi-pupae and semi-imagoes.
TABLE 2 poisoning effect of test samples on Prodenia litura larvae
The present invention has been described above by referring to a part of specific embodiments, and it should be noted that the above-mentioned specific embodiments are only used for further description of the present invention and do not represent a limitation to the scope of the present invention. Other insubstantial modifications and adaptations of the present invention can be made without departing from the scope of the present invention.
Sequence listing
<110> research institute of tropical biotechnology of Chinese tropical academy of agricultural sciences
<120> anhydride compound with prodenia litura poisoning activity, and preparation method and application thereof
<160>1
<170>SIPOSequenceListing 1.0
<210>1
<211>1265
<212>DNA
<213> Aspergillus fumigatus (Aspergillus fumigatus)
<400>1
cgaatggctc attaaatcag ttatcgttta tttgatagta ccttactaca tggatacctg 60
tggtaattct agagctaata catgctaaaa acctcgactt cggaaggggt gtatttatta 120
gataaaaaac caatgccctt cggggctcct tggtgaatca taataactta acgaatcgca 180
tggccttgcg ccggcgatgg ttcattcaaa tttctgccct atcaactttc gatggtagga 240
tagtggccta ccatggtggc aacgggtaac ggggaattag ggttcgattc cggagaggga 300
gcctgagaaa cggctaccac atccaaggaa ggcagcaggc gcgcaaatta cccaatcccg 360
acacggggag gtagtgacaa taaatactga tacggggctc ttttgggtct cgtaattgga 420
atgagtacaa tttaaatccc ttaacgagga acaattggag ggcaagtctg gtgccagcag 480
ccgcggtaat tccagctcca atagcgtata ttaaagttgt tgcagttaaa aagctcgtag 540
ttgaaccttg ggtctggctg gccggtccgc ctcaccgcga gtactggtcc ggctggacct 600
ttccttctgg ggaaccccat ggccttcact ggctgtgggg ggaaccagga cttttactgt 660
gaaaaaatta gagtgttcaa agcaggcctt tgctcgaata cattagcatg gaataataga 720
ataggacgtg cggttctatt ttgttggttt ctaggaccgc cgtaatgatt aatagggata 780
gtcgggggcg tcagtattca gctgtcagag gtgaaattct tggatttgct gaagactaac 840
tactgcgaaa gccttcgcca aggatgtttt cattaatcag ggaacgaaag ttaggggatt 900
gaagacgatc agataccgtt gtagttttaa ccataaacta tgccgactag ggatcgggcg 960
gtgtttttat gatgaccccc tcggcccctt acgagaaatc aaagtttttg ggttttgggg 1020
ggagtatggt cgcaaggctg aaacttaaag aaattgacgg aagggcaccc caaggcgtgg 1080
agcctgcggc ttaatttgac tcaacccggg gaaactcacc aggtccagac aaaataagga 1140
ttgacagatt gagagctctt tcttgatctt ttggatggtg gtgcatggcc gtttttagtt 1200
ggtggagtga tttgtttgct taattgcgat aacgaacgag acctcggccc ttaaatagcc 1260
cggtc 1265
Claims (6)
1. An acid anhydride compound with a prodenia litura poisoning activity is characterized in that: which has the structure as in formula (I):
（
）。
2. the method for preparing an acid anhydride compound having a prodenia litura poisoning activity according to claim 1, which comprises the steps of:
(1) activating an aspergillus fumigatus JRJ111048 with the preservation number of CGMCC No.14155 on a slant, inoculating the aspergillus fumigatus in an ME culture medium, performing shake culture at 26-30 ℃ for 3-5 days at 180-250 r.min < -1 >, inoculating the aspergillus fumigatus in the ME culture medium according to the inoculation amount of 3-10% of the volume percentage content, and performing shake culture at 26-30 ℃ for 180-250 r.min < -1 > for 12-15 days to obtain a fermentation liquid;
(2) extracting the fermentation liquor by using ethyl acetate with the same volume, and concentrating an ethyl acetate extract under reduced pressure until the ethyl acetate extract is dry to obtain a crude extract;
(3) suspending the crude extract with distilled water, sequentially extracting with chloroform and ethyl acetate of equal volume to obtain a chloroform extraction layer A, an ethyl acetate extraction layer B and a water layer part C, then carrying out silica gel open column chromatography on the ethyl acetate extraction layer B, carrying out gradient elution with chloroform-methanol at volume ratios of 100:0, 100:1, 100:2, 100:4, 100:8 and 0:100 to obtain sub-fractions B1, B2, B3, B4, B5 and B6, and carrying out ODS column chromatography and Sephadex-LH20 on the sub-fraction B2 for separation to obtain the anhydride compound with the spodoptera litura poisoning activity.
3. The method for preparing an acid anhydride compound having a prodenia litura poisoning activity according to claim 2, wherein the acid anhydride compound comprises: the ME culture medium 1L in the step (1) contains the following components by mass: 8-10 g of malt extract, 16-20 g of sucrose and 2-4 g of peptone, wherein the pH value of the ME culture medium is 7.0-7.2.
4. The method for preparing an acid anhydride compound having a prodenia litura poisoning activity according to claim 2, wherein the acid anhydride compound comprises: in the step (2), the fermentation liquor is extracted for 2-3 times by using ethyl acetate with the same volume, and the temperature of reduced pressure concentration is 40-60 ℃.
5. Use of the acid anhydride compound according to claim 1 for preparing a poisoning agent having a spodoptera litura poisoning effect.
6. Use according to claim 5, characterized in that: the poisoning agent is applied to crops of cotton, tobacco, soybean, taro, peanut, sesame, lotus root, Chinese cabbage, radish, mustard, spinach, leek or shallot for preventing and treating prodenia litura.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710932387.8A CN107722032B (en) | 2017-10-10 | 2017-10-10 | Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710932387.8A CN107722032B (en) | 2017-10-10 | 2017-10-10 | Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107722032A CN107722032A (en) | 2018-02-23 |
| CN107722032B true CN107722032B (en) | 2020-01-21 |
Family
ID=61208673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710932387.8A Active CN107722032B (en) | 2017-10-10 | 2017-10-10 | Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107722032B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116349656B (en) * | 2023-05-26 | 2023-08-22 | 云南省烟草公司昆明市公司 | Method for large-scale propagation of noctuid black egg bees |
-
2017
- 2017-10-10 CN CN201710932387.8A patent/CN107722032B/en active Active
Non-Patent Citations (3)
| Title |
|---|
| Effect of modifying the structure of Rubratoxin B on the acute toxicity to mice;Rose, H. Monica，等;《Biochemical Pharmacology》;19701231;第19卷(第2期);第612-615页 * |
| Neutral, alkaline and difference ultraviolet spectra of secondary metabolites from Penicillium and other fungi, and comparisons to published maxima from gradient high-performance liquid chromatography with diode-array detection;Russell, R.，等;《Journal of Chromatography》;19901231;第551卷;第195-221页 * |
| Talaromyces atroroseus, a New Species Efficiently Producing Industrially Relevant Red Pigments;Jens C. Frisvad，等;《PLOS ONE》;20131231;第8卷(第12期);第1-15页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107722032A (en) | 2018-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0593428B1 (en) | Myconematicide | |
| Wang et al. | Farming of a defensive fungal mutualist by an attelabid weevil | |
| CN102363750B (en) | Insecticidal fungus and application thereof | |
| Klingen et al. | Effect of brassicaceous plants on the survival and infectivity of insect pathogenic fungi | |
| Dara et al. | Endophytic colonization and pest management potential of Beauveria bassiana in strawberries | |
| CN110066739A (en) | A kind of muscardine SB010 and its application in the common setose thistle Malaysia and China of prevention and treatment | |
| CN114317293B (en) | High pathogenicity and high ultraviolet resistance space insect fungus strain SCAUHT18 for common thrips and application thereof | |
| CN102532247B (en) | Nematicidal compound derived from trichoderma virens as well as preparation method and application thereof | |
| Moricca et al. | Observations on the non-native thousand cankers disease of walnut in Europe’s southernmost outbreak | |
| CN106434362A (en) | Anti-ultraviolet high-toxicity meterhizium anisopliae mutant strain MaUV-1 and application thereof | |
| CN101892170B (en) | Entomopathogenic nematode symbiotic bacteria and application thereof | |
| CN107722032B (en) | Anhydride compound with prodenia litura poisoning activity and preparation method and application thereof | |
| CN105670938A (en) | Beauveria bassiana for intoxicating Holotrichia oblita and application thereof | |
| CN104988092B (en) | A kind of bacillus thuringiensis, preparation method and application | |
| CN114292760B (en) | High pathogenicity and high ultraviolet resistance space insect fungus strain SCAUHT38 for common thrips and application thereof | |
| CN114982769B (en) | Pesticide containing emamectin benzoate and beauveria bassiana as active ingredients and application of pesticide in prevention and treatment of common thrips | |
| CN114317294B (en) | High pathogenicity and high ultraviolet resistance space insect fungus strain SCAUHT56 for common thrips and application thereof | |
| CN113349203B (en) | Application of benzoic acid in preventing and controlling plant nematode diseases | |
| Al-Hazmi et al. | The effect of Arthrobotrys conoides on Meloidogyne incognita population densities in corn as influenced by temperature, fungus inoculum density, and time of fungus introduction in the soil | |
| CN111153797B (en) | Active substance for killing nematode and its preparing process and application | |
| KR20230047424A (en) | Indole alkaloids with fungicidal efficacy | |
| CN114540200B (en) | Space breeding beauveria bassiana strain SCAUHT30 with high pathogenicity to common thrips and application thereof | |
| CN114317292B (en) | Space breeding beauveria bassiana strain SCAUHT12 with high pathogenicity to common thrips and application thereof | |
| US20040151699A1 (en) | Bactericidal, bacteriostatic and fungicidal composition, comprising two or more live species of trichoderma and its preparation procedure, and a composition based on latex for a pruning cicatrizing that includes a latex base and a composition of two or more live species of trichoderma | |
| CN114317291B (en) | Space breeding beauveria bassiana strain SCAUHT21 with high pathogenicity to common thrips and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |