Pyrrole compound and application thereof
By using 2,5-dimethylpyrrole compounds as active ingredients, the problems of drug resistance, high toxicity and high production cost of Southern root knot nematodes have been solved, and high low-dose prevention and control and simplified production have been achieved, and large-scale application potential is achieved.
Patent Information
- Application Number
- CN202510631608.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-05-16
- Publication Date
- 2025-08-08
AI Technical Summary
Existing chemical pesticides and plant-source pesticides have problems such as drug resistance, high toxicity, low effect, high cost and difficulty in large-scale application in the prevention and control of southern root knot nematodes, and the effects of traditional microbial pesticides are unstable.
Using 2,5-dimethylpyrrole compounds as active ingredients, biopestic preparations were developed by destroying the dual mechanisms of osmotic pressure balance of nematode epidermal and mitochondrial membrane potential, with a concentration of 12.5~50 μg/ml, significantly improving the prevention and control effect and simplifying the extraction process from cigar cigarettes.
It has achieved low dose and efficient prevention and treatment of southern root knot nematodes, reduced drug resistance, reduced toxicity to non-target organisms, simplified production processes, reduced costs, and had the potential for large-scale production, and better effect when combined with avermectin.
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Figure CN120441465A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of compounds, in particular to a pyrrole compound and application thereof. Background Art
[0002] The southern root-knot nematode, Meloidogyne incognita, is characterized by its wide host range and extensive damage, affecting over 3,000 plant species worldwide. It primarily infects plant roots, damaging root structure and hindering nutrient absorption, resulting in stunted plants and reduced yields. The wounds caused by infection by the southern root-knot nematode serve as entry points for pathogenic fungi and bacteria, exacerbating the occurrence of complex diseases. Infections typically lead to widespread yield losses, and in severe cases, even complete crop failure (e.g., in Solanaceae and Cucurbitaceae crops). Exploring green and safe botanical pesticides is crucial to meet the requirements of green and healthy pest control.
[0003] Traditional synthetic chemical pesticides (such as organophosphates and carbamates) and biopesticides have significant drawbacks in controlling root-knot nematodes. Long-term, mono-use chemical pesticides are extremely common, leading to the rapid evolution of nematode resistance. For example, due to its single target, avermectin has led to nematode resistance in multiple regions. To achieve effective control, farmers are forced to increase the dosage, which further exacerbates environmental pressures. Furthermore, most chemical pesticides are highly toxic to non-target organisms, such as soil microorganisms and aquatic organisms. For example, thiazolyl can severely damage soil ecosystems. Furthermore, chemical pesticides have a long half-life in the environment, leading to the accumulation of heavy metals and organic pollutants in farmland. Existing botanical pesticides, such as matrine and azadirachtin, have complex active ingredients and low concentrations, requiring high dosages to achieve a certain mortality rate. Furthermore, their short duration of action makes them unsuitable for field control. Microbial pesticides, such as Paecilomyces lilacinus, are significantly affected by temperature and humidity. Their germination rate decreases under low temperatures or drought conditions, resulting in unstable control effectiveness. Furthermore, the extraction process for natural products is often complex. Isolating pyrethrins from pyrethrum requires multiple purification steps, including supercritical CO2 extraction and column chromatography, which is costly and difficult to scale up. Summary of the Invention
[0004] In view of the deficiencies of the prior art, the present invention provides a pyrrole compound that solves the problems of drug resistance, high toxicity, low efficacy and dystocia in the prior art.
[0005] To achieve the above objectives, the present invention is implemented through the following technical solutions: a pyrrole compound, the molecular structure of the compound is: .
[0006] A pyrrole compound is used in controlling southern root-knot nematodes in plants. The compound inhibits the activity of southern root-knot nematodes through a toxic effect. The compound is used at a concentration of 12.5 to 50 μg / ml, including a gradient of 50 μg / ml, 25 μg / ml, and 12.5 μg / ml. The corrected mortality rate after 72 hours of treatment is over 50%, and the toxicity is significantly higher than that of a 5% avermectin microcapsule suspension. Preferably, the toxicity of the compound to the southern root-knot nematode is concentration- and time-dependent, with an LC50 value of 40.182 μg / ml after treatment at a concentration of 50 μg / ml for 72 hours. The compound is extracted from cigar smoke.
[0007] A biological pesticide preparation for controlling southern root-knot nematodes, comprising the compound according to claim 1 as an active ingredient, and an agriculturally acceptable carrier or adjuvant, wherein the preparation is in the form of an aqueous solution or a microcapsule suspension.
[0008] The present invention provides a pyrrole compound and its application, which has the following beneficial effects: The present invention provides a pyrrole compound and its application. The 2,5-dimethylpyrrole provided by the present invention shows a breakthrough advantage in the prevention and control of root-knot nematodes. The corrected mortality rate of the compound against southern root-knot nematodes at a specific concentration is significantly higher than that of avermectin at the same concentration, and the LC50 value is significantly lower than that of avermectin, thereby achieving low-dose and high-efficiency prevention and control. As a natural tobacco leaf extract, 2,5-dimethylpyrrole has a short half-life in soil, and its degradation products are water and carbon dioxide, with no bioaccumulation risk. Its safety to non-target organisms is improved compared with chemical pesticides. The compound works through a dual mechanism of disrupting the nematode epidermal osmotic pressure balance and mitochondrial membrane potential. Compared with single-target drugs, it can reduce the nematode resistance mutation rate. The process for extracting 2,5-dimethylpyrrole from cigar tobacco is simplified, with high yield and low cost, and has the potential for large-scale production. When compounded with avermectin, the LC50 value is further reduced. The synergy coefficient shows that the two have a significant synergistic effect, which can reduce the amount of chemical pesticides used. DETAILED DESCRIPTION
[0009] The following will be combined with the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the embodiments described are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative efforts are within the scope of protection of the present invention.
[0010] The present invention provides a pyrrole compound and its application, which includes the following contents: The pure compound obtained by the test analysis was purchased and tested using the drug solution immersion method. Healthy and uniformly sized nematodes were selected as test nematodes to determine the toxicity of the compound solution. The test was carried out in a 24-well cell culture plate. The nematode suspension was first injected into the sample well. After the compound was accurately weighed, it was dissolved in sterile water to prepare a drug. The drug was mixed evenly with the nematode suspension to make the drug concentration 50μg / ml, 25μg / ml, and 12.5μg / ml. The drug was placed in a 25°C incubator. Each treatment was repeated three times, with 100 nematodes per repeat. A 5% avermectin microcapsule suspension was used as a positive control, and sterile water treatment was used as a blank control. 24, 48, and 72 hours after treatment, the death and survival of the nematodes in each treatment were checked respectively. The nematode mortality rate and the corrected mortality rate were calculated according to formula (1) and formula (2), respectively.
[0011] Method for judging whether nematodes are dead or alive: observe under a microscope. Those that are swimming and in an "S" shape are recorded as alive. In a static state, if the nematodes change shape significantly after being gently touched with an inoculation needle, they are recorded as alive; otherwise, they are recorded as dead.
[0012]
[0013]
[0014] The toxicity of 2,5-dimethylpyrrole to nematodes was determined by the drug solution immersion method, and the toxicity regression equation was calculated. The results are shown in Tables 1 and 2.
[0015] Table 1, Toxic effect of 2,5-dimethylpyrrole on southern root-knot nematode Table 2. Toxic activity and toxicity curve of 2,5-dimethylpyrrole against southern root-knot nematode From the above table, we can see that 2,5-dimethylpyrrole has a strong toxicity to southern root-knot nematodes. When treated with 50 μg / ml, the corrected mortality rate of southern root-knot nematodes was 45.97% after 72 hours. The LC values of southern root-knot nematodes at 24 hours, 48 hours and 72 hours were 50 The toxicity to southern root-knot nematodes was significantly higher than that of 5% avermectin microcapsule suspension.
[0016] While embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that various changes, modifications, substitutions, and variations may be made to these embodiments without departing from the principles and spirit of the invention, and that the scope of the invention is defined by the appended claims and their equivalents.
Claims
1. A pyrrole compound, characterized in that: The molecular structural formula of the compound is: .
2. The use of a pyrrole compound according to claim 1 in controlling southern root-knot nematodes, characterized in that: The compound inhibits the activity of southern root-knot nematodes through a toxic effect. The compound is used at a concentration of 12.5-50 μg / ml, including gradient concentrations of 50 μg / ml, 25 μg / ml, and 12.5 μg / ml. The corrected mortality rate after 72 hours of treatment reaches more than 50%, and the toxic activity is significantly higher than that of a 5% avermectin microcapsule suspension.
3. The use of a pyrrole compound in controlling southern root-knot nematodes according to claim 1, characterized in that: The compound has a concentration- and time-dependent toxicity to southern root-knot nematodes, with an LC50 value of 40.182 μg / ml after treatment at a concentration of 50 μg / ml for 72 hours. The compound is obtained by extracting cigar smoke.
4. A biological pesticide preparation for controlling southern root-knot nematodes, characterized in that: The preparation comprises the compound according to claim 1 as an active ingredient and an agriculturally acceptable carrier or adjuvant, and the preparation is in the form of an aqueous solution or a microcapsule suspension.