CN108617647B - Application of two compounds in preparation of nematocide - Google Patents
Application of two compounds in preparation of nematocide Download PDFInfo
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- CN108617647B CN108617647B CN201810365352.5A CN201810365352A CN108617647B CN 108617647 B CN108617647 B CN 108617647B CN 201810365352 A CN201810365352 A CN 201810365352A CN 108617647 B CN108617647 B CN 108617647B
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
- A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
- A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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Abstract
The invention relates to the technical field of pesticides and medicines, in particular to application of two compounds in preparing nematocides. The two compounds are safe and reliable, can effectively prevent and treat nematode diseases in agriculture, can expel nematode parasites in medical use, have no toxic or side effect and drug dependence on human bodies, are superior to the existing pesticides and medicines, and can be widely applied to preparation of drugs for killing nematodes.
Description
Technical Field
The invention relates to the technical field of pesticides and medicines, in particular to application of two compounds in preparing nematocides.
Background
The nematodes belong to the phylum of nematode animals, are recorded in various types and are seen everywhere in the world, wherein many types are parasitic, and the types of the parasitic nematodes recorded in China are as many as 25, and are popular, such as roundworms, pinworms, hookworms and the like. With the improvement of medical and health conditions and the like, the infection rate of soil-borne nematodes which are monitored and pathogenic in China in 2005-2013 is reduced from 20.88% to 3.12%, but the soil-borne nematodes still harm the physical health of people in a large amount. And the harm of agricultural and forestry nematodes is also great, which causes the reduction of yield and the extinction of agriculture (such as root-knot nematodes, which are estimated to cause the global crop loss to reach 1 hundred million dollars), the death of large-area trees (such as pine black nematodes) and the like, and threatens the food and ecological safety of China.
Research on drugs for resisting parasitic nematodes and agricultural harmful nematodes is always concerned, and has good agricultural and medical application potentials. The existing agricultural nematocides mainly have organophosphorus pesticides such as nematocides and the like, and have the defects of high toxicity and high residue; the medical insecticide is albendazole and also has certain side effects.
The traditional Chinese herbal medicine plays an undoubted role in the disease prevention and treatment of people, and the active ingredients are extracted from the traditional Chinese herbal medicine, so that the method is an important means and a technological front for independent research and development of new intellectual property medicines, accords with the research and development trend of international medicines, and has wide application prospect.
The existing research data show that some phenolic components of some traditional Chinese medicines have obvious nematicidal activity, and indicate nematicidal medicines for agriculture and medical treatment. The nematicidal active phenolic components are screened and found in the traditional Chinese medicine, and are synthesized by a chemical method. Therefore, the development of agricultural and medical nematicidal drugs with low toxicity and obvious curative effect has obvious social and economic benefits for human society.
Disclosure of Invention
In view of the above, the present invention provides the use of two compounds in the preparation of nematicidal agents. The two compounds have obvious curative effects on agricultural nematode diseases and human parasitic nematodes, and have high safety and no toxic or side effect. .
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides application of a compound shown as a formula I or a formula II in preparing nematocide,
the chemical name of the compound shown in the formula I is as follows: stilbostemin E as white powder, molecular weight 274, molecular formula C16H18O4CAS registry number 439900-95-5, alternative name: 3- [2- (3-hydroxy-5-methoxyphenyl) ethyl]2-methoxyphenol, which is reported in the literature to have antifungal, antiviral and antitumor activity. The compound source is obtained by extracting and separating Stemonaceae plants.
The chemical name of the compound shown in the formula II is as follows: stemantrene A is white powder, has a molecular weight of 300, and has a molecular formula of C18H22O4CAS registry number 674774-82-4, alternative name: 9, 10-dihydroxy-1, 5-dimethoxy-6-methyl-2, 7-phenanthrene diol and stemona phenanthrene A, wherein the compound is obtained by extracting and separating plants. The literature reports antifungal, antiviral and antitumor activity. The compound source is obtained by extracting and separating Stemonaceae plants.
Preferably, the nematodes are phytopathogenic nematodes and/or parasitic human nematodes.
Preferably, the nematicide further comprises a pharmaceutically acceptable adjuvant.
Preferably, the pharmaceutically acceptable auxiliary materials are one or more of a disintegrating agent, a lubricating agent, an adhesive or a dispersing agent.
Preferably, the dosage form of the nematocide is an aqueous preparation or a solid preparation.
Preferably, the solid preparation is a tablet, granule, capsule, powder or pill.
In the invention, the compound shown in the formula I or the formula II is obtained by extracting and separating from plants or obtained by chemical synthesis.
Preferably, the weight percentage of the compound shown in the formula I or the formula II in the nematocide is 1 to 99 percent.
Preferably, the weight percentage of the compound shown in the formula I or the formula II in the nematocide is 10-90%.
Preferably, the nematicidal agent further comprises other agents having nematicidal activity.
The invention provides application of two compounds in preparing nematocide. The two compounds are compounds shown in formula I or formula II. The invention has the technical effects that:
in a comparison test of the compound and organophosphorus pesticide linear phoxim and insecticide albendazole, the activity of the compound is superior to that of linear phoxim and albendazole, and the toxicity and residue are lower than those of linear phoxim and albendazole.
Meanwhile, the two compounds have no acute toxicity and long-term toxicity phytotoxicity to agricultural crops, the crops grow well, and no drug accumulation exists. The compound of the invention has no adverse reaction and no damage to organs in the research of animal acute toxicity and long-term toxicity of the compound. In clinical trials, the compound of the invention has obvious curative effect on parasite patients, and has no toxic or side effect and drug dependence.
The invention is safe and reliable, can effectively prevent and treat nematode diseases in agriculture, can expel nematode parasites in medical use, has no toxic or side effect and drug dependence on human bodies, is superior to the prior pesticide and medicine, and can be widely applied to the preparation of nematicidal drugs.
Detailed Description
The invention discloses application of two compounds in preparing nematocide, and a person skilled in the art can appropriately modify process parameters by referring to the content. It is expressly intended that all such similar substitutes and modifications which would be obvious to one skilled in the art are deemed to be included in the invention. While the methods and applications of this invention have been described in terms of preferred embodiments, it will be apparent to those of ordinary skill in the art that variations and modifications in the methods and applications described herein, as well as other suitable variations and combinations, may be made to implement and use the techniques of this invention without departing from the spirit and scope of the invention.
In the application of preparing the medicament for killing nematodes, the compound can be prepared into various agricultural or clinical conventional preparations according to the conventional preparation method in the field, for example, pharmaceutically acceptable auxiliary materials (such as a disintegrating agent, a lubricant, a binder, a dispersing agent and the like) can be added into the compound in an effective dose to prepare various oral medicaments, and the compound is preferably prepared into tablets, granules, capsules, powder, pills or oral liquid.
Various pharmaceutical products can be easily prepared by a conventional preparation method knowing the active ingredients, and auxiliary materials used in the preparation are well known in the art, such as carboxymethyl starch sodium, sucrose powder, honey, sesame oil, and the like.
The invention utilizes stilbostemin E and stemanthene A obtained by plant extraction and separation or a chemical synthesis method, can effectively kill agricultural pathogenic nematodes and human parasitic nematodes, has low toxic and side effects and drug dependence on human bodies, has better nematode killing experimental drug effect than the prior common pesticides and western medicines, and can be widely applied to agricultural nematode prevention and treatment and human parasitic nematode treatment drug preparation.
The bulk drugs or auxiliary materials used in the application of the two compounds in the preparation of the nematocide can be purchased from the market.
The invention is further illustrated by the following examples:
example 1: agricultural water solvent for preparing compound of the invention
Weighing the raw materials (unit: g) according to the weight: stilbostemin E and stemantrene A each 6g, Tween-602 g, water 50 mL.
Tween-60 was added to 50mL, heated to 50-60 ℃ and slowly added to stilbostemin E and stemantrene A, respectively, and filtered to obtain an aqueous solution.
For agricultural use in nematicidal applications, the formulated aqueous solution may be diluted to 2000mL with water for spraying or rhizosphere injection.
Example 2: capsules for preparing the compounds of the invention
Weighing the following raw materials (unit: g): stilbostemin E and stemanthrene A each 60 g.
Respectively adding stilbostemin E and stemantrene A into 100mL of ethanol, filtering, adding 1.8g of carboxymethyl starch sodium, mixing well, spray drying to prepare granules, and filling into No. 1 capsules to obtain capsules.
Example 3: tablets for preparing the compounds of the invention
Weighing the following raw materials (unit: g): stilbostemin E and stemanthrene A each 60 g.
Respectively adding stilbostemin E and stemantrene A into 100mL of ethanol, filtering, adding 1.8g of carboxymethyl starch sodium, fully mixing, spray drying to prepare granules, and conveying to a tablet press for tabletting to obtain the tablet.
Example 4: pellets for preparing the compounds of the invention
Weighing the following raw materials (unit: g): stilbostemin E and stemanthrene A each 60 g.
Respectively adding stilbostemin E and stemantrene A into 100mL of ethanol, filtering, adding 1.8g of carboxymethyl starch sodium, fully mixing, spray drying to prepare granules, adding 20g of pure sesame oil or honey, mixing, and delivering to a centrifugal pill making machine to prepare pills.
Example 5: nematicidal Activity of the Compounds of the invention
The nematicidal activity is evaluated by the lethal activity to the whole-tooth revival nematodes, and the safety is evaluated by the cytotoxic activity.
All compounds or samples to be tested were dissolved in 10. mu.L of dimethyl sulfoxide and then diluted with water (containing 0.3% v/v Tween-20) to a concentration of 25mg/mL of stock solution. The nematodes were incubated in oat media (20 g oatmeal, 20mL water in 200mL Erlenmeyer flasks, steam sterilized at 121 ℃ for 30 minutes) at 28 ℃ for 5-6 days. Then, a 6cm diameter petri dish was used to hold 300. mu.L of the prepared nematode suspension (approximately 200 head of a half-adult nematode). The test stock solution was added and gently stirred to bring the test compound to 25. mu.g/mL (half the effective dose IC measured)50At a concentration of 0.2, 1,5, 25, and 125. mu.g/mL). Dimethyl sulfoxide (10. mu.L) was dissolved in water (containing 0.3% v/v Tween-20) as a blank. Three replicates were tested for each test.
The relative nematode lethality (NA) for nematicidal activity was determined by counting the number of dead nematodes (n) under a microscope after 24 hours of incubation at 28 ℃>100) To obtain the final product. NA is determined by the formula NA ═ DN/SN × 100% (number of nematodes dead DN; number of all nematodes counted by SN, SN>100) And (4) calculating. Absolute nematode lethality RDR is given by the formula RDR ═ NAn-NA0(NAnRelative nematode mortality, NA, of Compounds0Relative lethality of blank). If any compound is absoluteNematode lethality greater than 40%, requires testing for concentration gradients (IC)50Absolute lethality at concentrations of 0.2, 1,5, 25, and 125 μ g/mL) and the Reed and Muench methods were used to calculate the half effective dose IC of this compound50。
TABLE 1 in vitro anti-nematicidal Activity of Compounds
The results in Table 1 show that the compound has stronger nematicidal activity, better than the prior organophosphorus nematicidal pesticide of the isazofos and the human insecticide albendazole, and EC50The values of 0.56 and 4.9mM are achieved, the toxicity is lower than that of the minimum positive albendazole, and the CC is50Greater than 50mM, thereby providing the compound with greater safety. This indicates that the compounds have good in vitro nematicidal activity and good safety.
Example 6: field experiments on the preparation of the Compound of the present invention
50 seedlings of cucumbers, tomatoes, eggplants and agilawood suffering from nematode diseases are taken, the plants grow thin and weak, the leaves fall off, and part of the leaves turn yellow.
1. The implementation method comprises the following steps: the inventive drug (mother solution of the compound prepared in example 1, diluted to 2000mL) was administered in an amount of 20mL per plant
2. Evaluation criteria for effects: and (5) after the plants grow, taking rhizosphere soil samples to detect the number of rhizosphere nematodes, and taking the positive control as the nematodide.
The method has the following advantages: the plant growth is recovered, the leaves turn green, and the rhizosphere nematodes disappear.
And partial effective: the plant growth fails to recover or die, and the rhizosphere nematodes disappear.
And (4) invalidation: the plant growth is not recovered or died, and the rhizosphere nematode does not disappear.
And (4) residual: after 10 days, 5g of rhizosphere soil sample is taken, water is turbid, the rhizosphere soil sample is extracted by ethyl acetate, and residue is quantitatively detected by a Gas chromatography-mass spectrometry (GC-MS) technology after concentration.
3. As a result: the medicament prepared by the compound can effectively kill rhizosphere harmful nematodes under most conditions, so that plants can recover growth, and a few plants are partially effective because the nematodes are deeply harmful and cannot recover or die.
TABLE 2 Compound field nematode control Activity experiments
Example 7: toxicity Studies of the Compounds of the invention
1. Acute toxicity study
The drug of the present invention (the compound powder in capsules prepared in example 2) was administered to Kunming mice by gavage at 1g/kg for 4 times per day with 6h intervals, and then normal diet was given to the mice to check the organs pathologically without the occurrence of pathological changes in the organs.
2. Long term toxicity study
The drug of the present invention (the compound powder in capsules prepared in example 2) was administered to Kunming mice by intragastric administration in medium and large dose groups (1g/kg, 2g/kg) 1 time per day for 14 days, and then the body weight, cardiac function, liver function, kidney function, electrocardiogram and other indicators were measured, and no significant abnormality was observed in the administration groups compared with the control group. The pathological examination of heart, liver, kidney, spleen, lung, stomach, duodenum, large intestine, small intestine, adrenal gland and genital organs, and the administration group has no obvious toxic change compared with the control group. The results show that the compound is safe and nontoxic, and can be used clinically.
Example 8: clinical trials of the Compound formulations of the present invention
1. Data of test object
There were 51 patients with stilbostemin E: age 5-30 years; 25 cases in men and 26 cases in women; the course of disease is 2 weeks-2 years; the main manifestations are poor appetite, abdominal pain, diarrhea, constipation, uneasy, irritability, easy fright, bruxism and other symptoms, and if the symptoms are met, the ascarid eggs can be seen in the fecal detection, which is in line with the clinical diagnosis of ascaris.
There were 48 patients with stemanthrene a: age 5-30 years; 24 cases in men and 24 cases in women; the course of disease is 2 weeks-2 years; the main manifestations are poor appetite, abdominal pain, diarrhea, constipation, uneasy, irritability, easy fright, bruxism and other symptoms, and if the symptoms are met, the ascarid eggs can be seen in the fecal detection, which is in line with the clinical diagnosis of ascaris.
2. Treatment method and treatment effect evaluation criteria: the compound capsule (example 2) of the present invention is administered orally at 300 mg/day, and is administered once before sleeping every night, to reduce the number of children under 12 years old to half, for two treatment courses.
3. The curative effect standard is as follows: after defecation, the ascarid corpses can be seen, and whether the ascarid eggs in the defecation of the patient disappear after treatment or not is detected.
The method has the following advantages: the ascarid in the stool on the second and third days is visible, and the ascarid eggs in the stool of the patient are invisible after treatment, so that whether the adverse symptoms disappear or not.
And partial effective: the ascarid in the stool was visible on the second and third days, and the ascarid eggs in the stool were still visible after treatment.
And (4) invalidation: no ascarid was found in the stools on the next and third days, and ascarid eggs in the stools of patients were still visible after treatment.
4. Clinical results
First, 51 and 48 patients with improved clinical chief complaints were not hospitalized.
Second, in 51 patients with various examination results stilbestemin E, 49 patients were not able to detect ascarid eggs in the stool after taking the medicine, 48 patients were able to see ascarid corpses, 47 patients had no adverse symptoms, and 4 patients were better.
Of 50 patients with stemanthrene a, 50 had no ascarid eggs detected in the stool after administration, of which 48 had a visible ascarid cadaver, 49 had no adverse symptoms, and 1 had a better condition.
And thirdly, the clinical results summarize 51 cases and 50 cases of patients who are clinically diagnosed with ascaris infection, and the patients are respectively treated by two compound capsules.
1. The results of the comprehensive observation of the clinical treatment of 51 cases and 50 cases of roundworm infection respectively show that the medicine has definite curative effect on the treatment of roundworm infection.
2. Toxic and side effects observation results: none of the treated patients had any adverse reactions, indicating that the drug of the present invention is safe to human body.
The clinical observation results show that the compound has obvious curative effect on treating ascaris infection, no toxic or side effect and no drug dependence.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. The application of the compound shown as the formula I or the formula II in preparing nematocide,
2. use according to claim 1, wherein the nematodes are agro-pathogenic nematodes and/or parasitic nematodes of the human body.
3. The use according to claim 1, wherein the nematicide further comprises a pharmaceutically acceptable adjuvant.
4. The use according to claim 1, wherein the pharmaceutically acceptable excipient is one or more of a disintegrant, a lubricant, a binder or a dispersant.
5. The use according to claim 1, wherein the nematicide is in the form of an aqueous or solid formulation.
6. The use according to claim 5, wherein the solid formulation is a tablet, granule, capsule, powder or pill.
7. The use according to claim 1, wherein the compound of formula I or formula II is isolated from a plant by extraction, or is obtained by chemical synthesis.
8. The use according to claim 1, wherein the compound of formula I or formula II is present in an amount of 1 to 99% by weight of the nematicide.
9. The use according to claim 1, wherein the compound of formula I or formula II is present in an amount of 10% to 90% by weight of the nematicide.
10. The use according to claim 1, wherein the nematicidal agent further comprises another agent having nematicidal activity.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101209059A (en) * | 2006-12-26 | 2008-07-02 | 河南农业大学 | Novel biological preparation for killing root-knot nematode and application method thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101209059A (en) * | 2006-12-26 | 2008-07-02 | 河南农业大学 | Novel biological preparation for killing root-knot nematode and application method thereof |
Non-Patent Citations (2)
| Title |
|---|
| A nematode larval motility inhibition assay for screening plant extracts and natural products;Stephen D. Lorimer等;《J. Agric. Food Chem.》;19961231;第44卷;摘要，第2843页 * |
| Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P.strobus and P. palustris;TAKAYUKI SUGA等;《Phytochtmistry》;19931231;第33卷(第6期);第1396页，第1397页表5，第1396页右栏，第1397页右栏 * |
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