An enoic acid compound and use thereof

CN122668014APending Publication Date: 2026-09-01YUNNAN AGRICULTURAL UNIVERSITY
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Patent Information

Application Number
CN202610986934.X
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2026-07-03
Publication Date
2026-09-01

AI Technical Summary

Technical Problem

[0003]当前防治南方根结线虫的主要手段依赖化学合成农药(如阿维菌素类)和传统生物源农药,但这些方法存在显著缺陷

Benefits of technology

本发明提供了一种烯酸类化合物及其应用,反-2-辛烯酸对南方根结线虫的毒杀活性显著优于传统化学农药,在50μg/ml浓度下处理24小时,校正死亡率可达99.56%,其LC50值为38.04μg/ml,较苦参碱降低60.20%。该化合物表现出明显的浓度依赖性毒杀效果,使用时的处理时间为24、48、72小时,且毒杀效果随浓度增加而显著增强,可通过梯度浓度灵活施用,在确保防效的同时减少用药量及环境风险。

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Abstract

This invention provides an olefinic acid compound and its application, relating to the field of compound technology. The olefinic acid compound is trans-2-octenoic acid, and its molecular structural formula is as follows: [Insert molecular structural formula here]. The compound is used to control southern root-knot nematodes. The effective application concentrations of the compound are 6.25 μg / ml, 12.5 μg / ml, 25 μg / ml, 50 μg / ml, 75 μg / ml, and 100 μg / ml. The 24-hour median lethal concentration (LD50) of the compound is 38.04 μg / ml. This compound exhibits a significant concentration-dependent toxic effect and can be flexibly applied through gradient concentrations, ensuring efficacy while reducing dosage and environmental risks.
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Description

Technical Field

[0001] This invention relates to the field of compound technology, specifically to an olefinic acid compound and its applications. Background Technology

[0002] The southern root-knot nematode, *Meloidogyne incognita*, is one of the world's most harmful soil-borne plant parasitic nematodes, posing a serious threat to agricultural production. According to statistics from the International Plant Protection Convention (IPPC), this nematode has infested 3,147 plant species, including those in the Solanaceae, Cucurbitaceae, and Fabaceae families, causing direct economic losses exceeding tens of billions of US dollars annually. Its unique biological characteristics and pathogenic mechanisms make it a major challenge to sustainable agricultural development. Faced with the problems of pesticide resistance and ecological risks associated with traditional chemical pesticides, the development of green control technologies is urgently needed. In recent years, plant-derived pesticides have received considerable attention due to their multiple biological activities and environmental safety; therefore, developing plant-derived pesticides is an important way to build an environmentally friendly integrated pest management system.

[0003] Currently, the main methods for controlling southern root-knot nematodes rely on chemically synthesized pesticides (such as abamectin) and traditional biopesticides, but these methods have significant drawbacks. First, chemical pesticide resistance is severe: long-term use of chemical pesticides with a single mechanism of action (such as abamectin) leads to a rapid increase in nematode resistance. For example, comparative experiments in the document show that matrine's LC50 value against second-instar nematodes reached as high as 95.57 μg / ml after 24 hours, significantly lower than the compounds in this technology, and requires frequent application at high doses, increasing costs and environmental burden. Second, chemical pesticide residues pose a significant hazard: traditional chemical pesticides are difficult to degrade and easily accumulate in soil and crops, threatening food safety and ecological balance. Third, the efficacy of traditional biopesticides is unstable: existing plant- or microbial-derived pesticides have complex active ingredients and low concentrations of effective substances (e.g., crude extracts require high doses), and are limited by extraction processes, making industrial-scale production difficult. For example, conventional tobacco extracts require multiple extractions and the active ingredients are not clearly defined, leading to difficulties in quality control and limiting practical application. Fourth, existing technologies lack specificity: most pesticides lack concentration and time dependence in their toxicity to nematodes, making it impossible to achieve efficient and precise control, resulting in high control costs and poor effectiveness.

[0004] Trans-2-octenic acid (also known as (E)-2-octenic acid or 2-octenic acid) is a natural medium-chain monounsaturated fatty acid. It is a tobacco aroma substance found in flue-cured tobacco leaves and can be used as an edible flavoring. Summary of the Invention

[0005] The purpose of this invention is to provide a new use for trans-2-octenic acid, namely, the application of trans-2-octenic acid in the control of southern root-knot nematodes. This not only expands the application scope of trans-2-octenic acid, but also provides a new approach to the control of southern root-knot nematodes.

[0006] Application of trans-2-octenic acid in the control of root-knot nematodes in southern China: This invention is achieved through the following technical solution: an olefinic acid compound, wherein the olefinic acid compound is trans-2-octenoic acid, and the molecular structural formula of the compound is: .

[0007] Preferably, the compound is used to control southern root-knot nematodes.

[0008] Preferably, the effective concentration of the compound is 6.25 μg / ml, 12.5 μg / ml, 25 μg / ml, 50 μg / ml, 75 μg / ml, or 100 μg / ml.

[0009] Preferably, the treatment time for the compound is 24, 48, or 72 hours.

[0010] Preferably, the median lethal concentration of the compound after 24 hours is 38.04 μg / ml.

[0011] Preferably, the toxic effect of the compound increases significantly with increasing concentration.

[0012] This invention provides an olefinic acid compound and its applications. It possesses the following beneficial effects: This invention provides an octenoic acid compound and its application. Trans-2-octenoic acid exhibits significantly superior toxic activity against southern root-knot nematodes compared to traditional chemical pesticides. At a concentration of 50 μg / ml, after 24 hours of treatment, the corrected mortality rate reaches 99.56%, with an LC50 value of 38.04 μg / ml, which is 60.20% lower than that of matrine. This compound demonstrates a clear concentration-dependent toxic effect, with treatment times of 24, 48, and 72 hours. The toxic effect significantly increases with increasing concentration, allowing for flexible application through gradient concentrations, ensuring efficacy while reducing pesticide dosage and environmental risks.

[0013] This invention provides an olefinic acid compound and its application. The compound is derived from secondary metabolites of plants and has safe and environmentally friendly properties.

[0014] This invention provides an olefinic acid compound and its application, which can be developed into a single active ingredient biopesticide formulation, or it can be used in combination with other pesticides or adjuvants, providing a brand-new technical solution for the control of plant parasitic nematodes and expanding the application pathways of biopesticides. Detailed Implementation

[0015] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0016] Example 1: This embodiment of the invention provides an olefinic acid compound and its application. This enoic acid compound is trans-2-octenic acid, and its molecular structural formula is as follows: , This compound is mainly used to control southern root-knot nematodes. It has strong toxic activity and can be developed into a single-component biological pesticide or combined with other formulations to provide a new solution for nematode control. Its effective application concentrations are 6.25 μg / ml, 12.5 μg / ml, 25 μg / ml, 50 μg / ml, 75 μg / ml, and 100 μg / ml, with a median lethal concentration of 38.037 μg / ml. When using the compound, the treatment time is 24, 48, and 72 hours, and the toxic effect increases significantly with increasing concentration.

[0017] Example 2: This embodiment of the invention provides an olefinic acid compound and its application, comprising the following: Purified compounds were purchased, and the contact toxicity assay was performed. Healthy, uniformly sized nematodes were selected as test nematodes to determine the toxic activity of the compound solution. The experiment was conducted in 24-well cell culture plates. The nematode suspension was first injected into the sample wells. The compound was accurately weighed and dissolved in 0.625% dimethyl sulfoxide aqueous solution to prepare the agent. The agent was mixed evenly with the nematode suspension to make the agent concentrations 100 μg / ml, 75 μg / ml, 50 μg / ml, 25 μg / ml, 12.5 μg / ml, and 6.25 μg / ml. The plates were placed in an incubator at 20℃. Each treatment was repeated in 3 replicates, with 100 nematodes per replicate. Matrine was used as a positive control, and treatment with 0.625% dimethyl sulfoxide aqueous solution was used as a blank control. After treatment, the mortality and survival of nematodes in each treatment were checked 24 days later. The nematode mortality rate and corrected mortality rate were calculated according to formulas (1) and (2), respectively.

[0018] Methods for determining whether nematodes are alive or dead: Under a microscope, nematodes that are swimming or in an "S" shape are considered alive. If the nematode remains still when gently touched with an inoculation needle while it is at rest, it is considered dead.

[0019]

[0020] The toxic activity of trans-2-octenic acid against nematodes was determined by the contact toxicity method, and the toxicity regression equation was calculated. The results are shown in Tables 1 and 2.

[0021] Table 1. Toxicity of trans-2-octenic acid against southern root-knot nematodes

[0022] Note: "-" indicates a corrected mortality rate of 0-10.0%, with no causative activity; "+" indicates a corrected mortality rate of 10.1-30.0%, with weak causative activity; "++" indicates a corrected mortality rate of 30.1-50.0%, with moderate causative activity; "+++" indicates a corrected mortality rate of 50.1-80.0%, with strong causative activity; "++++" indicates a corrected mortality rate of 80.1-100.0%, with active causative activity.

[0023] Table 2. Toxicity and toxicity curves of trans-2-octenic acid against southern root-knot nematodes.

[0024] As shown in the table above, trans-2-octenic acid has strong toxic activity against southern root-knot nematodes. Treatment of southern root-knot nematodes with 50 μg / ml resulted in a corrected mortality rate of 99.56% after 24 hours. Its toxic activity against southern root-knot nematodes is significantly higher than that of matrine. The LC50 value of 38.037 μg / ml after 24 hours is concentration-dependent, and it can be flexibly applied through gradient concentrations to reduce dosage and environmental risks.

[0025] Although embodiments of the invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made to these embodiments without departing from the principles and spirit of the invention, the scope of which is defined by the appended claims and their equivalents.

Claims

1. An olefinic acid compound, characterized in that: The enoic acid compound is trans-2-octenic acid, and the molecular structural formula of the compound is: .

2. The olefinic acid compound according to claim 1, characterized in that: The compound is used to control southern root-knot nematodes.

3. The application of an olefinic compound according to claim 2, characterized in that: The effective concentrations of the compound are 6.25 μg / ml, 12.5 μg / ml, 25 μg / ml, 50 μg / ml, 75 μg / ml, and 100 μg / ml.

4. The application of an olefinic compound according to claim 2, characterized in that: The treatment time for the compound was 24, 48, and 72 hours.

5. The application of an olefinic compound according to claim 2, characterized in that: The 24-hour median lethal concentration of the compound was 38.04 μg / ml.

6. The application of an olefinic compound according to claim 3, characterized in that: The toxic effect of the compound increases significantly with increasing concentration.

7. A preparation for controlling southern root-knot nematodes, characterized in that, The active ingredient includes the olefinic compound as described in claim 1.