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CN116508755A - Application of compound with nematoda resisting activity - Google Patents

Application of compound with nematoda resisting activity Download PDF

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Publication number
CN116508755A
CN116508755A CN202210066385.6A CN202210066385A CN116508755A CN 116508755 A CN116508755 A CN 116508755A CN 202210066385 A CN202210066385 A CN 202210066385A CN 116508755 A CN116508755 A CN 116508755A
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root
knot
nematode
compound
nematodes
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秦玉坤
王林松
李鹏程
邢荣娥
刘松
于华华
李荣锋
李克成
范兆乾
高堃
战将
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Institute of Oceanology of CAS
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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Abstract

本发明属于农业病虫害防治技术领域,涉及一种化合物具有抗线虫活性的应用。以呋喃环及羧酸基团为结构的化合物在制备抗线虫中的应用,其杀线活性显著高于结构类似物四氢呋喃甲酸,且能够有效抑制根结线虫的活性,降低根结线虫的运动性和卵孵化率,杀灭根结线虫。本发明具有操作方法简单,绿色环保,高效的杀线活性,在沙土条件下能够有效抑制根结线虫对寄主植物的侵染性,且对植物生长无明显毒性,在防控根结线虫病方面具有良好的应用前景,能够应用于根结线虫的防治以及作为先导化合物进行新杀线农药制剂的开发。

The invention belongs to the technical field of prevention and control of agricultural diseases and insect pests, and relates to the application of a compound with anti-nematode activity. The application of the compound with the structure of furan ring and carboxylic acid group in the preparation of anti-nematodes, its nematicidal activity is significantly higher than that of the structural analog tetrahydrofurancarboxylic acid, and can effectively inhibit the activity of root-knot nematodes and reduce the motility of root-knot nematodes And egg hatching rate, kill root-knot nematode. The invention has the advantages of simple operation method, environmental protection, high-efficiency nematicidal activity, can effectively inhibit the infectivity of root-knot nematodes to host plants under sandy soil conditions, and has no obvious toxicity to plant growth, and is effective in preventing and controlling root-knot nematode diseases It has a good application prospect and can be used in the control of root-knot nematodes and as a lead compound in the development of new nematodecidal pesticide preparations.

Description

一种化合物具有抗线虫活性的应用Application of a compound with anti-nematode activity

技术领域:Technical field:

本发明属于农业病虫害防治技术领域,涉及一种化合物具有抗根结线虫活性的应用。The invention belongs to the technical field of prevention and control of agricultural diseases and insect pests, and relates to the application of a compound with anti-root-knot nematode activity.

背景技术:Background technique:

植物寄生性线虫不仅对各国的生态环境造成了严重的破坏,而且给农业生产带来了巨大的经济损失。而在植物寄生线虫中,专性寄生于植物根部的根结线虫(Meloidogynespp.)是一种分布最为广泛,危害最为严重的寄生线虫,被认为是“世界上最具破坏性的植物病原物”。根结线虫因其侵染的特殊性、病害的隐蔽性而难以取得较为理想的防控效果,目前已成为植物保护领域的世界性难题。并且由于地域性差异,同一化合物对根结线虫的敏感性会存在不同。然而,传统商业化的化学杀线剂由于具有高毒、致癌、污染环境等副作用问题,已逐渐被弃用。因此,深入研究高效低毒的杀根结线虫天然化合物,并以此作为先导化合物进行新农药创制已成为根结线虫病防治研究的重要内容。Plant parasitic nematodes have not only caused serious damage to the ecological environment of various countries, but also brought huge economic losses to agricultural production. Among plant parasitic nematodes, root-knot nematode (Meloidogynes pp.) obligately parasitic on plant roots is the most widely distributed and most harmful parasitic nematode, and is considered to be "the most destructive plant pathogen in the world". . Root-knot nematode has become a worldwide problem in the field of plant protection because of the particularity of its infection and the concealment of the disease. And due to regional differences, the sensitivity of the same compound to root-knot nematodes may vary. However, traditional commercial chemical nematicides have been gradually abandoned due to side effects such as high toxicity, carcinogenicity, and environmental pollution. Therefore, in-depth research on natural compounds that kill root-knot nematodes with high efficiency and low toxicity, and use them as lead compounds to create new pesticides has become an important content of root-knot nematode control research.

发明内容:Invention content:

本发明的目的在于克服现有技术的不足,提供一种化合物具有抗根结线虫活性的应用。The purpose of the present invention is to overcome the deficiencies of the prior art and provide an application of a compound with anti-root-knot nematode activity.

为实现上述目的,本发明采用技术方案为:In order to achieve the above object, the technical solution adopted by the present invention is:

一种化合物具有抗线虫活性的应用,以呋喃环及羧酸基团为结构的化合物在制备抗线虫中的应用。An application of a compound having anti-nematode activity, and an application of a compound having a structure of a furan ring and a carboxylic acid group in the preparation of an anti-nematode.

以呋喃环及羧酸基团为结构的化合物在制备抗根结线虫中的应用。The application of the compound with the structure of furan ring and carboxylic acid group in the preparation of root-knot nematode resistance.

所述根结线虫为南方根结线虫。The root-knot nematode is root-knot nematode incognita.

所述化合物为2-呋喃甲酸,结构式如下:Described compound is 2-furan formic acid, and structural formula is as follows:

所述2-呋喃甲酸的添加量为50μg.mL-1到200μg.mL-1The added amount of the 2-furancarboxylic acid is 50 μg.mL -1 to 200 μg.mL -1 .

本发明所提供的2-呋喃甲酸在杀灭根结线虫,能够有效抑制根结线虫的活性,降低根结线虫的运动和卵孵化率,杀灭根结线虫,可以用于杀根结线虫的农药制剂。此外,2-呋喃甲酸结构简单,可以作为先导化合物进行新农药的创制。The 2-furancarboxylic acid provided by the present invention can effectively inhibit the activity of root-knot nematodes in killing root-knot nematodes, reduce the movement and egg hatching rate of root-knot nematodes, kill root-knot nematodes, and can be used to kill root-knot nematodes Pesticide formulations. In addition, 2-furancarboxylic acid has a simple structure and can be used as a lead compound for the creation of new pesticides.

对上述2-呋喃甲酸杀根结线虫生测实验具体为:在无菌24孔板中用400μL不同浓度的2-呋喃甲酸溶液(25-150μg.mL-1)重悬根结线虫,使试验体系中根结线虫数量调整为大约50条,无菌蒸馏水为阴性对照,30μg.mL-1噻唑膦为阳性对照。25℃避光培养24小时后,体式显微镜下观察根结线虫形态,计算根结线虫的存活及死亡条数,重复以上实验。视野下松材线虫呈僵直状不动为死亡,否则为存活,分别计算不同浓度梯度下24小时的根结线虫校正死亡率,结果用SPSS 17.0进行统计分析。计算公式如下所示:The bioassay of the above-mentioned 2-furancarboxylic acid against root-knot nematodes is as follows: resuspend root-knot nematodes with 400 μL of different concentrations of 2-furancarboxylic acid solutions (25-150 μg.mL −1 ) in a sterile 24-well plate, and make the test The number of root-knot nematodes in the system was adjusted to about 50, sterile distilled water was used as a negative control, and 30 μg.mL -1 thiazole was used as a positive control. After culturing at 25°C in the dark for 24 hours, observe the morphology of root-knot nematodes under a stereomicroscope, count the number of surviving and dead root-knot nematodes, and repeat the above experiment. B. xylophilus in the field of vision was dead if it was stiff and immobile, otherwise it was considered alive. The 24-hour corrected mortality rate of root-knot nematodes under different concentration gradients was calculated respectively, and the results were statistically analyzed with SPSS 17.0. The calculation formula is as follows:

本发明所具有的优点:The advantages that the present invention has:

本发明具有操作方法简单,绿色环保,高效的杀线活性,且在沙土条件下能够有效抑制根结线虫对寄主植物(例如黄瓜)的侵染性,且对植物生长无明显毒性,在控制根结线虫病方面有良好的应用前景,能够应用于杀根结线虫新农药制剂的开发。The invention has the advantages of simple operation method, environmental protection, high-efficiency nematicidal activity, and can effectively inhibit the infectivity of root-knot nematodes to host plants (such as cucumbers) under sandy soil conditions, and has no obvious toxicity to plant growth, and is effective in controlling root knot nematodes. Knot nematode has a good application prospect and can be applied to the development of new pesticide preparations for killing root-knot nematodes.

本发明真菌源2-呋喃甲酸在24h对根结线虫的LC50约为37.75μg.mL-1,在相同浓度下(30μg.mL-1),能够有效抑制根结线虫的活性,降低根结线虫的运动性和卵孵化率,杀灭根结线虫,进而体现其杀线能力极强、稳定性极高;同时其杀线活性甚至接近于目前国际上普遍应用的杀线药物噻唑膦,且其骨架结构较噻唑膦更加简单,因而具有较强的杀线剂开发潜力,为开发防治根结线虫病的新型药物打下坚实的基础。The LC 50 of the fungal source 2-furancarboxylic acid of the present invention against root-knot nematodes in 24 hours is about 37.75 μg.mL -1 , and at the same concentration (30 μg.mL -1 ), it can effectively inhibit the activity of root-knot nematodes and reduce root-knot nematodes The motility and egg hatching rate of nematodes can kill root-knot nematodes, which further reflects its strong nematodecidal ability and high stability; at the same time, its nematodecidal activity is even close to that of thiazophosphine, a nematodecidal drug commonly used in the world at present, and Its skeleton structure is simpler than that of thiazophosphine, so it has strong nematocide development potential and lays a solid foundation for the development of new drugs for the prevention and treatment of root-knot nematode.

附图说明:Description of drawings:

图1为本发明实施例提供的2-呋喃甲酸对南方根结线虫杀线活性效果图;其中,CK:对照组蒸馏水处理组线虫;P-30:30μg.mL-1四氢呋喃甲酸处理组线虫;F-30:30μg.mL-1噻唑膦处理组线虫(*代表显著性差异,*p<0.05,**p<0.01,and***p<0.001,ns代表无显著性差异)。Fig. 1 is the diagram of the nematicidal activity effect of 2-furancarboxylic acid on root-knot nematode incognita provided by the examples of the present invention; wherein, CK: nematodes in the control group treated with distilled water; P-30: nematodes in the 30 μg.mL -1 THF treated group; F-30: 30 μg.mL -1 thiazophos-treated nematodes (* represents significant difference, *p<0.05, **p<0.01, and ***p<0.001, ns represents no significant difference).

图2为本发明实施例提供的2-呋喃甲酸对南方根结线虫运动能力的影响图(*代表显著性差异,*p<0.05,**p<0.01,and***p<0.001)。Fig. 2 is a diagram of the effect of 2-furancarboxylic acid on the motility of Meloidogyne incognita provided by the examples of the present invention (* represents a significant difference, *p<0.05, **p<0.01, and ***p<0.001).

图3为本发明实施例提供的2-呋喃甲酸对南方根结线虫卵孵化的影响图(*代表显著性差异,*p<0.05,**p<0.01,and***p<0.001)。Figure 3 is a diagram of the influence of 2-furancarboxylic acid provided by the examples of the present invention on the hatching of Meloidogyne incognita eggs (* represents a significant difference, *p<0.05, **p<0.01, and ***p<0.001) .

图4为本发明实施例提供的2-呋喃甲酸的生防潜力评估图,CK:对照组蒸馏水处理组线虫;2-FA-L,2-FA-M,2-FA-H:分别是100μg.mL-1,150μg.mL-1,200μg.mL-1 2-呋喃甲酸处理组;M为阳性对照组300μg.mL-1威百亩。Fig. 4 is the biocontrol potential assessment figure of 2-furancarboxylic acid provided by the embodiments of the present invention, CK: control group distilled water treatment group nematode; 2-FA-L, 2-FA-M, 2-FA-H: 100 μ g respectively .mL -1 , 150μg.mL -1 , 200μg.mL -1 2-furancarboxylic acid treatment group; M is the positive control group 300μg.mL -1 Mebam.

具体实施方式:Detailed ways:

以下结合实例对本发明的具体实施方式做进一步说明,应当指出的是,此处所描述的具体实施方式只是为了说明和解释本发明,并不局限于本发明。The specific embodiments of the present invention will be further described below in conjunction with examples. It should be noted that the specific embodiments described here are only for illustrating and explaining the present invention, and are not intended to limit the present invention.

下述各实施例中记载的根结线虫为南方根结线虫。The root-knot nematode described in each of the following Examples is Meloidogyne incognita.

实施例1、2-呋喃甲酸杀根结线虫活性测定。Example 1. Determination of the root-knot nematode killing activity of 2-furancarboxylic acid.

在无菌24孔板中用400μL不同浓度的2-呋喃甲酸溶液(25-150μg.mL-1)重悬根结线虫,使各试验体系中根结线虫数量调整为大约50条作为实验组,无菌蒸馏水为阴性对照,30μg.mL-1四氢呋喃甲酸溶液作为对照组,30μg.mL-1噻唑膦为阳性对照;而后对上述各组于25℃避光培养24小时后,体式显微镜下观察根结线虫形态,计算根结线虫的存活及死亡条数,重复以上实验视野下松材线虫呈僵直状不动为死亡,否则为存活,分别计算不同浓度梯度下24小时的根结线虫校正死亡率,结果用SPSS 17.0进行统计分析。计算公式如下所示:Resuspend root-knot nematodes in 400 μL of different concentrations of 2-furoic acid solution (25-150 μg.mL -1 ) in a sterile 24-well plate, so that the number of root-knot nematodes in each test system was adjusted to about 50 as the experimental group. Bacterial distilled water was used as negative control, 30 μg.mL -1 tetrahydrofuran formic acid solution was used as control group, and 30 μg.mL -1 thiazolyl phosphine was used as positive control; then the above-mentioned groups were incubated at 25°C in the dark for 24 hours, and the root knots were observed under a stereomicroscope. Nematode morphology, calculate the number of survival and death of root-knot nematodes, repeat the above experimental field of view, pine wood nematodes are dead in a stiff state, otherwise they are alive, and calculate the 24-hour corrected mortality of root-knot nematodes under different concentration gradients. The results were statistically analyzed using SPSS 17.0. The calculation formula is as follows:

参见图1结果显示,与对照组蒸馏水处理组相比,25μg.mL-1的2-呋喃甲酸对根结线虫具有显著的致死活性,在浓度为75μg.mL-1时,2-呋喃甲酸对根结线虫的致死率约为94%。相同浓度下(30μg.mL-1),2-呋喃甲酸对根结线虫的致死活性优于其结构类似物四氢呋喃甲酸,与商业化杀线剂噻唑膦并无显著性差异。同时,2-呋喃甲酸在24小时对根结线虫的半致死浓度为26.68-41.75μg.mL-1Referring to Figure 1, the results show that compared with the control group distilled water treatment group, 25 μg.mL -1 of 2-furan formic acid has significant lethal activity to root-knot nematodes, and when the concentration is 75 μg.mL -1 , 2-furan formic acid has a significant lethal activity on Root-knot nematode has a fatality rate of about 94%. At the same concentration (30μg.mL -1 ), the lethal activity of 2-furancarboxylic acid against root-knot nematodes was better than that of its structural analog tetrahydrofurancarboxylic acid, and there was no significant difference with the commercial nematicide thiazophos. At the same time, the half-lethal concentration of 2-furancarboxylic acid to root-knot nematodes in 24 hours was 26.68-41.75μg.mL -1 .

实施例2、2-呋喃甲酸对根结线虫运功的影响。Example 2. The effect of 2-furancarboxylic acid on the motility of root-knot nematode.

在2-呋喃甲酸对根结线虫运功影响的实验中,每组大约50条根结线虫分别浸泡于浓度分别为50,75,100μg.mL-1的2-呋喃甲酸溶液(溶剂为水溶液)中,25℃孵育24小时。相同条件下,浸泡于蒸馏水中的根结线虫作为对照。每个实验重复三次。In the experiment of the effect of 2-furancarboxylic acid on the movement of root-knot nematodes, about 50 root-knot nematodes in each group were respectively soaked in 2-furancarboxylic acid solutions with concentrations of 50, 75, and 100 μg.mL -1 (solvent is aqueous solution) Incubate at 25°C for 24 hours. Under the same conditions, root-knot nematodes immersed in distilled water were used as controls. Each experiment was repeated three times.

根结线虫运功测试:在2-呋喃甲酸对根结线虫运功影响的实验中,根结线虫头部每分钟摆动的次数被用来评估根结线虫运动性强弱。Root-knot nematode movement test: In the experiment of the effect of 2-furancarboxylic acid on the root-knot nematode movement, the number of swings of the head of the root-knot nematode per minute was used to evaluate the mobility of the root-knot nematode.

结果显示,随着2-呋喃甲酸浓度的升高,根结线虫每分钟头部摆动的次数逐渐降低。当浓度为75μg.mL-1时,根结线虫几乎丧失了运动活性(图2)。The results showed that as the concentration of 2-furoic acid increased, the number of head swings per minute of root-knot nematodes gradually decreased. When the concentration was 75 μg.mL -1 , the root-knot nematode almost lost its motility (Fig. 2).

实施例3、2-呋喃甲酸对根结线虫卵孵化的影响。Example 3. Effect of 2-furancarboxylic acid on hatching of root-knot nematode eggs.

在2-呋喃甲酸对虫卵孵化抑制实验中,每组大约50个线虫卵分别浸泡于浓度分别为50,75,100,150μg.mL-1 2-呋喃甲酸溶液中,25℃孵育12天。相同条件下,浸泡于蒸馏水中的虫卵作为对照,每个实验重复三次。In the experiment on the inhibition of egg hatching by 2-furoic acid, about 50 nematode eggs in each group were soaked in 2-furoic acid solutions with concentrations of 50, 75, 100, and 150 μg.mL -1 , and incubated at 25°C for 12 days . Under the same conditions, eggs soaked in distilled water were used as controls, and each experiment was repeated three times.

结果显示,2-呋喃甲酸对线虫卵孵化具有明显的抑制作用。线虫卵孵化率随着2-呋喃甲酸浓度的升高而降低,当浓度为50μg.mL-1时,线虫卵孵化率仅为13%,显著低于对照组蒸馏水处理组的33%(图3)。The results showed that 2-furoic acid had a significant inhibitory effect on the hatching of nematode eggs. The hatching rate of nematode eggs decreased with the increase of the concentration of 2-furoic acid. When the concentration was 50 μg.mL -1 , the hatching rate of nematode eggs was only 13%, which was significantly lower than the 33% of the control group treated with distilled water ( image 3).

实施例4、2-呋喃甲酸在活体条件下防效评价。Example 4. Evaluation of the control effect of 2-furancarboxylic acid under in vivo conditions.

通过温室条件下试管实验,评价2-呋喃甲酸对根结线虫的防治效果:每组大约200条根结线虫分别接种于含100(2-FA-L),150(2-FA-M),200(2-FA-H)μg.mL-1 2-呋喃甲酸的砂质土壤中,然后温室条件下培养21天;同时以商业化杀线剂威百亩作为阳性对照组。Through test tube experiments under greenhouse conditions, the control effect of 2-furancarboxylic acid on root-knot nematodes was evaluated: about 200 root-knot nematodes in each group were respectively inoculated in 100 (2-FA-L), 150 (2-FA-M), 200(2-FA-H)μg.mL -1 2-furancarboxylic acid in sandy soil, and then cultivated under greenhouse conditions for 21 days; at the same time, the commercial nematicide metamac was used as a positive control group.

活体测试结果表明,2-呋喃甲酸对根结线虫具有显著的防控效果,且防治效果与剂量呈正相关性。在沙土条件下,100μg.mL-1的2-呋喃甲酸能够显著减少黄瓜根结的数量,抑制率约为56%;在150μg.mL-1时,防治效果较好,抑制率大约为83%;而在200μg.mL-1时,2-呋喃甲酸对黄瓜根结线虫具有大约100%的防治效果,在该浓度下,防效与阳性对照300μg.mL-1的威百亩相近(表1)。此外,活体测试结果表明,高浓度2-呋喃甲酸(300μg.mL-1)对植物生长并没有显著的毒性(图4)。The results of in vivo tests showed that 2-furancarboxylic acid had a significant control effect on root-knot nematodes, and the control effect was positively correlated with the dosage. Under sandy soil conditions, 100μg.mL -1 of 2-furancarboxylic acid can significantly reduce the number of cucumber root knots, with an inhibition rate of about 56%; at 150 μg.mL -1 , the control effect is better, with an inhibition rate of about 83% and at 200 μg.mL -1 , 2-furancarboxylic acid has about 100% control effect on cucumber root-knot nematode, and at this concentration, the control effect is close to the metabam of positive control 300 μg.mL -1 (Table 1 ). In addition, the in vivo test results showed that high concentration of 2-furancarboxylic acid (300 μg.mL -1 ) had no significant toxicity to plant growth (Fig. 4).

表1:2-呋喃甲酸对南方根结线虫防效分析Table 1: Analysis of the control effect of 2-furancarboxylic acid on Meloidogyne incognita

Claims (5)

1.一种化合物具有抗线虫活性的应用,其特征在于:以呋喃环及羧酸基团为结构的化合物在制备抗线虫中的应用。1. An application of a compound having anti-nematode activity, characterized in that: the application of a compound having a structure of a furan ring and a carboxylic acid group in the preparation of an anti-nematode. 2.按权利要求1所述的化合物具有抗线虫活性的应用,其特征在于:以呋喃环及羧酸基团为结构的化合物在制备抗根结线虫中的应用。2. The application of the compound according to claim 1 having anti-nematode activity, characterized in that: the application of the compound with furan ring and carboxylic acid group as the structure in the preparation of anti-root-knot nematodes. 3.按权利要求2所述的化合物具有抗线虫活性的应用,其特征在于:所述根结线虫为南方根结线虫。3. The application of the compound according to claim 2 having anti-nematode activity, characterized in that: the root-knot nematode is root-knot nematode incognita. 4.按权利要求1-3任意一项所述的化合物具有抗线虫活性的应用,其特征在于:所述化合物为2-呋喃甲酸,结构式如下:4. according to the application that the compound described in any one of claims 1-3 has anti-nematode activity, it is characterized in that: described compound is 2-furoic acid, and structural formula is as follows: 5.按权利要求4所述的化合物具有抗线虫活性的应用,其特征在于:所述2-呋喃甲酸的添加量为50μg.mL-1到200μg.mL-15. The application of the compound according to claim 4 having anti-nematode activity, characterized in that: the added amount of the 2-furancarboxylic acid is 50 μg.mL −1 to 200 μg.mL −1 .
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1603758A (en) * 1977-05-27 1981-11-25 Schering Ag Fungicidally active furancarboxylic acid anilides and their manufacture and use
CN108779092A (en) * 2015-12-30 2018-11-09 杜邦公司 Nematicidal heterocycleamide
CN111226935A (en) * 2020-03-20 2020-06-05 赵沛基 Pesticide containing furan compound and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1603758A (en) * 1977-05-27 1981-11-25 Schering Ag Fungicidally active furancarboxylic acid anilides and their manufacture and use
CN108779092A (en) * 2015-12-30 2018-11-09 杜邦公司 Nematicidal heterocycleamide
CN111226935A (en) * 2020-03-20 2020-06-05 赵沛基 Pesticide containing furan compound and application thereof
CN111727970A (en) * 2020-03-20 2020-10-02 赵沛基 Pesticide containing furan compound and application thereof

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