CN112715542A - Preparation method of crotonaldehyde diterpenoid compound and application of crotonaldehyde diterpenoid compound in preparation of nematicidal pesticide - Google Patents
Preparation method of crotonaldehyde diterpenoid compound and application of crotonaldehyde diterpenoid compound in preparation of nematicidal pesticide Download PDFInfo
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
- C07C69/33—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety esterified with hydroxy compounds having more than three hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
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Abstract
The invention relates to a preparation method of a crotonaldehyde diterpenoid compound and application of the crotonaldehyde diterpenoid compound in preparation of a nematicidal pesticide, and belongs to the technical field of agriculture. Use of a crotonaldehyde diterpenoid or a preparation containing a crotonaldehyde diterpenoid for the preparation of a nematicidal pesticide, characterized in that: the crotonalane diterpenoid compound has the following chemical structural formula:
Description
Technical Field
The invention relates to a preparation method of a crotonaldehyde diterpenoid compound and application of the crotonaldehyde diterpenoid compound in preparation of a nematicidal pesticide, and belongs to the technical field of agriculture.
Background
Plant parasitic nematodes live and breed by absorbing plant nutrients and transmitting other plant pathogens to cause secondary disease to plants, causing serious damage to agricultural production and causing economic losses of approximately 1570 billion dollars per year. The methods for preventing and treating nematodes commonly used in agricultural production at present mainly comprise resistant variety breeding, biological prevention, chemical prevention and the like. The chemical control means which is convenient to operate and quick in effect is widely used by farmers, but the chemical control means repeatedly used in large quantities can cause the pesticide content in the product and the soil to exceed the standard, so that people pay more and more attention to the research of a new method for effectively controlling the plant parasitic nematodes with ecological reasonability. A safe and efficient compound is screened from a natural product, and the compound is directly developed into a new biological pesticide or is used as a model to synthesize a new safer and more efficient nematicide, so that the development of innovative biological pesticides is the main direction. The active substances derived from plants are more easily degraded by nature, have less pollution to the environment and are safer to crop production, and the screening of natural pesticide active molecules from plants attracts extensive attention all over the world.
Euphorbia fischeriana (Euphorbia fischeriana) is a plant of Euphorbia of Euphorbiaceae, is a perennial herb, is widely distributed in northeast China and is rich in resources. The root is a traditional Chinese medicine, and is commonly used for treating edema, ascites, skin diseases, intestinal parasites and the like. The euphorbia fischeri has abundant and various chemical components including diterpenes, triterpenes, phenols and the like.
Disclosure of Invention
The invention aims to provide a novel crotonaldehyde diterpenoid compound and an extraction method thereof, and also provides an application of the crotonaldehyde diterpenoid compound in preparing a nematicidal pesticide. The invention identifies a novel crotonalane diterpenoid compound from the ethyl acetate part of the root, stem and leaf of Euphorbia fischeriana (E.fischeriana) of Euphorbia (Euphorbia), through activity-oriented separation, and the activity screening has strong nematicidal activity, particularly the Euphorbia fischeriana root extract has the best nematicidal activity.
Use of a crotonaldehyde diterpenoid or a preparation containing a crotonaldehyde diterpenoid for the preparation of a nematicidal pesticide, characterized in that: the crotonalane diterpenoid compound has the following chemical structural formula:
the preparation containing the crotonaldehyde diterpenoid compound takes the crotonaldehyde diterpenoid compound as an active component and also comprises auxiliary materials. The crotonaldehyde diterpenoid compound can be used alone or mixed with other auxiliary materials in the process of killing nematodes.
Preferably, the nematode is meloidogyne incognita or cyst nematode.
Preferably, the crotonaldehyde diterpenoid is extracted from at least one of the root, stem, leaf of Euphorbia fischeriana (e.fischeriana) of the genus Euphorbia (Euphorbia).
Further preferably, the crotonaldehyde diterpenoid is extracted from the root of Euphorbia fischeriana (e.fischeriana) of Euphorbia (Euphorbia).
Further, the crotonaldehyde diterpenoid compound is prepared by the following method: extracting root, stem or leaf of Euphorbia fischeriana with methanol, concentrating, and extracting with ethyl acetate to obtain extract; and separating and purifying the obtained extract for several times to obtain the crotonaldehyde diterpenoid compound.
Still further, the separation is purified as: taking ethyl acetate extract of Euphorbia fischeriana L.F.Chen, and sequentially separating and purifying by repeated silica gel column chromatography, MCI column chromatography and gel column chromatography with nematicidal activity as guide to obtain crotonane diterpenoid compound.
Another object of the present invention is to provide a nematicidal pesticide.
A nematicidal pesticide, the active ingredient of which is a crotonaldehyde diterpenoid compound having the following chemical structure:
the pesticide of the invention has the function of preventing and treating nematodes. The function of the invention for preventing and treating the nematode is the function of non-therapeutic nematode prevention and treatment.
Further, the nematode is meloidogyne incognita or cyst nematode.
When the pesticide of the invention is used, the pesticide acts on nematodes or/and their habitat.
The invention has the beneficial effects that: the invention discloses a crotonaldehyde diterpenoid and application thereof in preparing a nematicide. The roots, stems and leaves of Euphorbia fischeriana (E.fischeriana) of Euphorbia of Euphorbiaceae (euphorbiae) provided by the invention can poison various plant parasitic nematodes in various forms, and a novel crotonalane diterpene compound is separated from the plant, has particularly outstanding poisoning activity on the plant parasitic nematodes through activity screening, can be used for preparing nematicides, reduces the number of the plant parasitic nematodes in agricultural production, reduces the harm of the parasitic nematodes and increases the yield of crops.
Detailed Description
The following non-limiting examples are presented to enable those of ordinary skill in the art to more fully understand the present invention and are not intended to limit the invention in any way.
The test methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Isolation and characterization of the Compounds crotonane diterpene Compounds used in the examples below
1. Extraction of root, stem and leaf of Euphorbia fischeriana
Adopting a methanol extraction method to respectively weigh 100g of root, stem and leaf of euphorbia stellera chamaejasme collected in the field, and respectively preparing root, stem and leaf extracts, specifically: extracting with methanol at room temperature for 24 hr for 3 times, mixing extractive solutions, concentrating with rotary evaporator to obtain methanol extract, extracting with ethyl acetate for 3 times, and concentrating to obtain ethyl acetate extract.
Selecting soil after planting cucumber and tomato, sieving (removing dead branches and large pieces of soil), measuring the water content in the soil, and then mixing the extracts of the root, stem and leaf of euphorbia stellera chamaejasme with the soil according to the mass ratio of 1: 100. Each of the treated soils was divided into 30 parts by weight and placed in pots, and the control group was 30 parts by weight of soil without extract added thereto, each part being the same as the treated group, and cultured in a nematode incubator at 25 ℃. The water content in each box was measured daily to ensure that soil nematodes were not disturbed by water loss. Counting the same time of one day after adding Euphorbia fischeriana and stirring uniformly until the next day, and separating the nematodes in the soil in 1, 4, 7, 10, 13 and 16 days respectively.
Separation of nematodes in soil: 100g of soil is weighed in each flowerpot and soaked in water, the mixture is fully stirred and then stands for 3 minutes, and supernatant is filtered by a group of sieves of 40 meshes, 80 meshes and 400 meshes. And (3) washing the soil and the nematodes on the 400-mesh sieve into a centrifuge tube, centrifuging at 2000rpm for 5 minutes, discarding the supernatant, adding a sucrose solution (673g/L), centrifuging at 2000rpm for 2 minutes, pouring the supernatant into a 500-mesh sieve, washing with clear water for 3 times to remove the sucrose solution, collecting the nematodes, counting the survival number of the nematodes under a microscope, and repeating 3 times. The results are shown in Table 1.
TABLE 1 number of surviving heads of nematodes in soil (heads/100 g) with different treatments
2. Separation and purification of crotonaldehyde diterpenoid compounds in euphorbia stellera root extract
Crushing a dried root sample (4Kg) of euphorbia stellera champ, leaching for 24h at room temperature by using methanol, extracting for 3 times, combining extracting solutions, concentrating by using a rotary evaporator, concentrating to obtain a methanol extract, extracting the methanol extract by using ethyl acetate for 3 times, and concentrating to obtain 100g of ethyl acetate extract. After dissolving it in 200mL chloroform/acetone (v/v 1:1), the sample was stirred with silica gel (200-300 mesh), loaded on a column for crude separation, gradient eluted with chloroform/acetone (v/v 10:0, 9:1, 8:2, 7:3, 0:10), detected by TLC, and the same fractions were combined to obtain 7 main fractions (fractions) (Fr.1-7). Wherein chloroform/acetone 10:0(v/v) part (Fr.3) (20g) is decolorized with macroporous resin, methanol part (Fr.3.2) is subjected to silica gel column chromatography, petroleum ether/acetone (10:0, 9:1, 8:2, 2:1, 0:10) is gradient eluted, and petroleum ether/acetone (9:1) part (Fr.3.2.2) (8g) is treated with MCI-gel (50-100% methanol/water, methanol, acetone) to obtain 7 sub-parts; 65% methanol/water (Fr.3.2.2.2) (5g) Compound 1(89mg) was obtained by repeated silica gel column chromatography and Sephadex LH-20 (acetone) column chromatography.
Compound 1 has the following chemical structure:
process for preparing 1-crotonaldehyde diterpene compound1The H NMR data are as follows:
1compound 1: the mixture is colorless and oily,1H NMR(600MHz,methanol-d4)δ:7.54(1H,brs,H-1),2.52(1H,d,H-5a),2.43(1H,d,J＝19.0Hz,H-5b),5.60(1H,d,J＝4.5Hz,H-7),3.06(1H,m,H-8),3.16(1H,s,H-10),2.04(1H,m,H-11),2.10(1H,dt,J＝7 and 14.6Hz,H-12a),1.54(1H,dd,J＝10.9 and 14.6Hz,H-12b),0.86(1H,overlap,H-14),1.17(1H,s,H-16),1.07(1H,s,H-17),0.90(3H,d,J＝6.5Hz,H-18),1.74(3H,d,J＝1.5Hz,H-19),3.93(2H,q,J＝12.8Hz,H-20),2.33(2H,t,J＝7.3Hz,H-2'),1.29(2H,overlap,H-3'),1.61(2H,dd,J＝7.0 and 14.1Hz,H-4'),1.28(1H,overlap,H-13'),0.85(3H,overlap,H-14'),0.87(3H,overlap,H-15').13C NMR(methanol-d4,150MHz):δ160.9(d,C-1),134.8(s,C-2),210.6(s,C-3),74.8(s,C-4),38.6(t,C-5),142.0(s,C-6),130.4(d,C-7),40.0(d,C-8),77.6(s,C-9),57.2(d,C-10),37.5(d,C-11),33.1(t,C-12),65.0(s,C-13),33.3(d,C-14),24.2(s,C-15),23.5(q,C-16),15.9(q,C-17),19.1(q,C-18),10.2(q,C-19),68.3(t,C-20),177.5(s,C-1'),35.3[t,C-2'),28.2(t,C-3'),25.9(t,C-4'),30.1～31.1(t,C-5'～11'),37.8(t,C-12'),35.7(d,C-13'),11.8(q,C-14'),19.7(q,C-15').
example 1 screening of Dictyotane diterpenoid Compounds for nematicidal Activity
Collecting tomato diseased roots infected with root-knot nematodes and soybean diseased roots infected with cyst nematodes. Cleaning diseased roots with oocysts, picking the oocysts under a dissecting mirror, performing surface disinfection for 3min by using 3% NaClO solution, and cleaning for 3 times by using sterile water. And (3) picking oocysts into 0.5% NaClO solution, oscillating for 20min, sieving with 200-mesh, 325-mesh and 500-mesh standard sieves once, and leaching the eggs on the 500-mesh sieve with sterile water. And (3) placing the egg liquid into an incubator, culturing at 25 ℃, and collecting nematodes for later use when a large number of larvae of J2 are hatched.
The poisoning effect of compound 1 on nematodes was determined according to the immersion method. 985. mu.L of fresh M9 buffer was added to the 24-well plate, 10. mu.L of nematode suspension was added simultaneously, the sample to be tested was dissolved in methanol, and 5. mu.L of the sample solution was added to the 24-well plate with a concentration gradient of 50, 25, 12.5, 6.25 and 3.125. mu.g/mL. The same equivalent methanol treatment served as a negative control. All tests were repeated 4 times and incubated at 25 ℃. Observing the death number of the nematodes under a dissecting mirror after 24h, 48h and 72h respectively, counting, and calculating LD50。
TABLE 2 nematicidal Activity (LD) of Compound 150,μg/mL)
Example 2 crotonane diterpenoid Compounds in vivo verification of nematicidal Activity
Culturing tomato seedlings to 3-4 true leaves, transplanting the seedlings into a small flowerpot (diameter of 12cm), and culturing one tomato seedling per pot. And transplanting the tomatoes into southern root-knot second-instar larvae after 1 week, wherein about 1000 tomatoes per pot are used. Three days later, the sample and abamectin (positive control, 10mg each) were made into a solution to be added to the tomato roots, the blank control was added to the corresponding solvent, and 5 replicates were set for each treatment. Then the tomato seedlings are placed in a greenhouse for culturing, and a certain amount of water is added periodically, preferably without water seepage. And after 30 days, digging out the tomato roots, putting the tomato roots into clear water to wash away soil, counting the root-knot nematode morbidity, recording the root-knot grade according to disease symptoms, and calculating the disease index.
TABLE 3 control of Meloidogyne incognita by Compound 1
The experimental results show that the compound has certain poisoning activity on various crop pests, has particularly obvious poisoning activity on soil nematodes, and has an inhibition rate as high as 77.34%.
The above embodiments are merely illustrative, and not restrictive, and those skilled in the art can make various changes and modifications without departing from the spirit and scope of the invention. Therefore, all equivalent technical solutions also belong to the scope of the present invention, and the protection scope of the present invention should be defined by the claims.
Claims (7)
1. Use of a crotonaldehyde diterpenoid or a preparation containing a crotonaldehyde diterpenoid for the preparation of a nematicidal pesticide, characterized in that: the crotonalane diterpenoid compound has the following chemical structural formula:
2. use according to claim 1, characterized in that: the nematode is Meloidogyne incognita or cyst nematode.
3. Use according to claim 1, characterized in that: the crotonaldehyde diterpenoid compound is prepared by the following method: extracting root, stem or leaf of Euphorbia fischeriana with methanol, concentrating, and extracting with ethyl acetate to obtain extract; and separating and purifying the obtained extract for several times to obtain the crotonaldehyde diterpenoid compound.
4. Use according to claim 3, characterized in that: the separation and purification are as follows: taking ethyl acetate extract of Euphorbia fischeriana L.F.Chen, and sequentially separating and purifying by repeated silica gel column chromatography, MCI column chromatography and gel column chromatography with nematicidal activity as guide to obtain crotonane diterpenoid compound.
5. A nematicidal pesticide, characterized by: the active component is a crotonaldehyde diterpenoid compound which has the following chemical structural formula:
6. the insecticide according to claim 1, wherein: the pesticide has the function of preventing and controlling nematodes.
7. The insecticide according to claim 1, wherein: in use, the pesticide is applied to the nematodes or/and their habitat.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115536532A (en) * | 2022-11-09 | 2022-12-30 | 中日友好医院(中日友好临床医学研究所) | Crotonalane diterpenoid compound and preparation method, pharmaceutical composition and application thereof |
| CN115611720A (en) * | 2022-12-04 | 2023-01-17 | 中日友好医院(中日友好临床医学研究所) | Novel ent-strobane alkane diterpenoid compound, preparation method thereof, pharmaceutical composition and application |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115536532A (en) * | 2022-11-09 | 2022-12-30 | 中日友好医院(中日友好临床医学研究所) | Crotonalane diterpenoid compound and preparation method, pharmaceutical composition and application thereof |
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| CN115611720A (en) * | 2022-12-04 | 2023-01-17 | 中日友好医院(中日友好临床医学研究所) | Novel ent-strobane alkane diterpenoid compound, preparation method thereof, pharmaceutical composition and application |
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Application publication date: 20210430 |