Application of nitrostyrolene compound in preventing or controlling or resisting plant pathogenic nematodes and preparation of nitrostyrolene compound

Nitrostyrene compounds address the inadequacies of existing nematode control methods by offering a potent and environmentally safer alternative for managing root-knot and pine wilt nematodes, enhancing agricultural productivity and reducing ecological impact.

CN119678922APending Publication Date: 2025-03-25GAUNGXI TIANYUAN BIOCHEM
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Patent Information

Application Number
CN202411985951.9
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2024-12-31
Publication Date
2025-03-25

AI Technical Summary

Technical Problem

Current methods for controlling plant parasitic nematodes, such as root-knot nematodes and pine wilt nematodes, are inadequate due to the development of resistance to chemical pesticides, leading to significant agricultural losses and ecological concerns.

Method used

Development of a novel agricultural formulation using nitrostyrene compounds, specifically β-nitrostyrene and its derivatives, which exhibit potent nematocidal activity against root-knot nematodes and pine wilt nematodes, offering a new class of pesticides.

Benefits of technology

The nitrostyrene compounds demonstrate high efficacy in killing these nematodes, providing a promising solution for developing new pesticides that are environmentally safer and more effective than traditional chemicals.

✦ Generated by Eureka AI based on patent content.

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Abstract

The invention relates to application of a nitrostyrolene compound in preventing, controlling or resisting plant pathogenic nematodes and a preparation of the nitrostyrolene compound, and relates to the field of pesticides. The nitrostyrene compound is selected from the group consisting of beta-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-beta-nitrostyrene, trans-4-bromo-beta-nitrostyrene, 4-methoxy-beta-nitrostyrene, trans-4-(2-nitrovinyl) cyanobenzene, 1-(3-fluorophenyl)-2-nitroethylene, (E)-1-fluoro-2-(2-nitrovinyl) and one or more of benzene. The nitrostyrene compound shows excellent insecticidal activity on plant root-knot nematodes and pine wood nematodes, has the advantages of simple structure, easiness in synthesis, good control effect and the like, and has a good application prospect in the aspect of controlling root-knot nematode diseases and pine wood nematode diseases. The compound can be applied to development of novel pesticide preparations for killing root-knot nematodes and pine wood nematodes.
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Description

Technical Field

[0001] The present invention relates to the field of pesticides, and in particular to an application of a nitrostyrene compound in preventing or controlling or resisting plant pathogenic nematodes and a preparation thereof, and specifically to preventing and controlling agricultural diseases caused by root-knot nematodes (Meloidogyne) and pine wood nematodes (Bursaphelenchus xylophilus). Background Art

[0002] The information disclosed in this background technology section is only intended to enhance the understanding of the overall background of the invention and should not be regarded as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to a person skilled in the art.

[0003] Nematodes, especially plant parasitic nematodes such as root-knot nematodes and pine wood nematodes, are common and important pests in agriculture, posing a serious threat to plant health and yield. Root-knot nematodes, tiny organisms that are usually invisible to the naked eye, invade plant roots, destroy root structure, and hinder the plant's absorption of water and nutrients. Their infection can cause slow plant growth, yellowing leaves, root deformities, and even crop death in severe cases. Pine wood nematodes can cause the entire parasitic tree to wither and die rapidly, causing pine wood nematode disease. The disease spreads quickly and is extremely difficult to prevent and control, seriously affecting ecological security, and also severely impacting the market for pine wood panels and ornamental pine wood. Globally, crop losses caused by nematodes amount to billions of dollars each year, seriously affecting food security and farmers' livelihoods.

[0004] At present, chemical control is still the main way to control plant nematode diseases. Due to the different nematode species, different infection levels and different crop types, it is difficult to achieve ideal results in nematode control. Traditional nematode control methods mainly rely on chemical pesticides. However, chemical pesticides may not only cause environmental pollution and ecological imbalance, but also induce nematode resistance to drugs, increasing the difficulty of control. Therefore, seeking safe and effective new compounds has become one of the current research hotspots.

[0005] Nitrostyrene compounds are a class of organic compounds containing nitro and styrene structures. As an important chemical raw material, this type of compound is widely used in chemical synthesis, material science, drug development and other fields due to its special chemical properties and structure. The stability of the benzene ring structure itself and the electron-withdrawing properties of the nitro group greatly reduce the electron cloud density of the benzene ring, making this type of compound extremely stable during use. At present, there are no reports on the use of nitrostyrene compounds for the prevention and control of plant nematode diseases. Summary of the invention

[0006] Purpose of the Invention

[0007] The purpose of the present invention is to provide a use of nitrostyrene compounds in preventing or controlling or resisting plant pathogenic nematodes and a preparation thereof. The present invention finds that nitrostyrene compounds have good nematicidal activity, especially excellent activity against root-knot nematodes and pine wood nematodes, and are expected to be developed into a new type of agricultural nematicide.

[0008] Solution

[0009] To achieve the purpose of the present invention, in a first aspect, the present invention provides a use of a nitrostyrene compound in preventing, controlling or resisting plant pathogenic nematodes.

[0010] In a second aspect, a preparation containing nitrostyrene compounds is provided for use in preventing, controlling or resisting plant pathogenic nematodes.

[0011] Optionally, it is used to control various plant diseases caused by root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes.

[0012] In the first aspect or the second aspect, the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, trans-4-(2-nitrovinyl)benzonitrile, 1-(3-fluorophenyl)-2-nitrovinyl, and (E)-1-fluoro-2-(2-nitrovinyl)benzene; wherein the chemical structural formula of each nitrostyrene compound is as follows:

[0013]

[0014] In the first aspect or the second aspect, the pathogenic nematode includes at least one of root-knot nematodes and pine wood nematodes;

[0015] Optionally, the pathogenic nematodes include root-knot nematodes, and the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, 1-(3-fluorophenyl)-2-nitrobenzene, and (E)-1-fluoro-2-(2-nitrovinyl)benzene;

[0016] Optionally, the pathogenic nematodes include pine wood nematodes, and the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, 1-(3-fluorophenyl)-2-nitrobenzene, and (E)-1-fluoro-2-(2-nitrovinyl)benzene; optionally, the nitrostyrene compound includes trans-4-bromo-β-nitrostyrene.

[0017] In the first aspect or the second aspect, the dosage form of the nitrostyrene compound is one or more of granules, dry suspensions, water suspensions, dispersible oil suspensions, microcapsule suspensions, wettable powders, emulsifiable concentrates, water emulsions, water dispersible granules, and seed treatment agents;

[0018] Optionally, the preparation of the nitrostyrene compound preparation also includes an auxiliary agent, and the auxiliary agent is selected from one or more of a dispersant, a wetting agent, a filler, an emulsifier, a thickener, a dispersion medium, a disintegrant, a solvent, a preservative, an antifreeze agent, a specific gravity regulator, a defoaming agent, an oil phase wall material, an aqueous phase wall material, and water.

[0019] In a third aspect, there is provided an insecticide containing a nitrostyrene compound for preventing or controlling or resisting plant pathogenic nematodes, which contains a nitrostyrene compound and an agriculturally acceptable adjuvant;

[0020] Optionally, the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, trans-4-(2-nitrovinyl)benzonitrile, 1-(3-fluorophenyl)-2-nitrovinyl, (E)-1-fluoro-2-(2-nitrovinyl)benzene; wherein the chemical structural formula of each nitrostyrene compound is as follows:

[0021]

[0022] Optionally, the pathogenic nematodes include at least one of root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes.

[0023] Further, the dosage form of the insecticide is one or more of granules, dry suspensions, water suspensions, dispersible oil suspensions, microcapsule suspensions, wettable powders, emulsifiable concentrates, water emulsions, water dispersible granules, and seed treatment agents;

[0024] Optionally, the agriculturally acceptable adjuvant is selected from one or more of synergists, dispersants, wetting agents, fillers, emulsifiers, thickeners, dispersion media, disintegrants, solvents, preservatives, antifreeze agents, specific gravity regulators, defoamers, oil phase wall materials, water phase wall materials, and water;

[0025] Optionally, one or more of commercial insecticides, miticides, fungicides, anti-plant virus agents and plant activators are also included.

[0026] Further, the dosage form of the insecticide is a granule, which includes the following raw materials in parts by weight: 1-20 parts of nitrostyrene compounds, 3-4 parts of wetting agents, 1.5-3.5 parts of dispersants, 0.2-3 parts of disintegrants, 0.2-3 parts of binders, and 68.5-93 parts of fillers; optionally, it includes the following raw materials in parts by weight: 5-20 parts of nitrostyrene compounds, 4 parts of wetting agents, 1.5-3.5 parts of dispersants, 2 parts of disintegrants, 2 parts of binders, and 68.5-85.5 parts of fillers;

[0027] Furthermore, the formulation of the insecticide is an aqueous suspension, which includes the following raw materials in parts by weight: 2 to 50 parts of nitrostyrene compounds, 3 to 5 parts of wetting agents, 1 to 3.5 parts of dispersants, 0 to 2 parts of antifreeze agents, 0 to 2 parts of thickeners, 0 to 2 parts of preservatives, 0.1 to 1 parts of defoaming agents, and 37.8 to 90 parts of water;

[0028] Furthermore, the formulation of the insecticide is a microcapsule suspension, which includes the following raw materials in parts by weight: 2 to 10 parts of nitrostyrene compounds, 10 to 20 parts of oily solvents, 1.5 to 3 parts of dispersants, 3 to 6 parts of wetting agents, 1 to 2 parts of binders, 3 parts of capsule wall materials, 0 to 2 parts of thickeners, 0.1 to 1 parts of defoaming agents, and 63 to 80 parts of water;

[0029] Furthermore, the formulation of the insecticide is a wettable powder, which includes the following raw materials in parts by weight: 20 to 40 parts of nitrostyrene compounds, 1 to 3 parts of dispersants, 3 to 8 parts of wetting agents, and 50 to 80 parts of fillers; optionally, it includes the following raw materials in parts by weight: 30 to 40 parts of nitrostyrene compounds, 1 to 3 parts of dispersants, 3 to 8 parts of wetting agents, and 50 to 63 parts of fillers.

[0030] In a fourth aspect, a method for reducing browning caused by plant pathogenic nematode pests is provided, wherein the pesticide described in the third aspect is diluted and sprayed or mixed and spread on the soil or plant rhizomes to be treated. Optionally, the pathogenic nematode includes at least one of a root-knot nematode and a pine wood nematode; and optionally, the root-knot nematode includes a southern root-knot nematode.

[0031] In a fifth aspect, a method for using the insecticide of the third aspect is provided, characterized in that the insecticide of the third aspect is diluted and sprayed or mixed and spread on the soil or plant rhizomes to be treated, and the dosage of the active ingredient is 10-18 g / mu. Optionally, the pathogenic nematode includes at least one of a root-knot nematode and a pine wood nematode; optionally, the root-knot nematode includes a southern root-knot nematode.

[0032] Beneficial Effects

[0033] The present invention finds that nitrostyrene compounds exhibit excellent insecticidal activity against plant root-knot nematodes and pine wood nematodes, and have the advantages of simple structure, easy synthesis, good control effect, etc., have good application prospects in controlling root-knot nematode disease and pine wood nematode disease, and can be used in the development of new pesticide preparations for killing root-knot nematodes and pine wood nematodes. DETAILED DESCRIPTION

[0034] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are 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 creative work are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "including" or its variations such as "comprising" or "including" will be understood to include the stated elements or components, without excluding other elements or other components.

[0035] In addition, in order to better illustrate the present invention, numerous specific details are provided in the specific embodiments below. It should be understood by those skilled in the art that the present invention can also be implemented without certain specific details. In some embodiments, raw materials, elements, methods, means, etc. well known to those skilled in the art are not described in detail, so as to highlight the main purpose of the present invention.

[0036] The raw materials such as nitrostyrene compounds and fluopyram of the present invention are all commercially available products. The percentage or proportion of each component in the following examples is measured by weight.

[0037] Test Example 1: Determination of the activity of nitrostyrene compounds in killing root-knot nematodes

[0038] Test reagents: The nitrostyrene compound was dissolved in 1 mL of DMSO, and then 0.5 mL of the solution was drawn, to which 0.5 mL of sterile water and a drop of Tween 80 were added to dilute the solution to the required concentrations, including 50 μg / mL and 12.5 μg / mL.

[0039] Test methods : Dilute the southern root-knot nematode solution to 2000 / mL. Pipette 90μL of the southern root-knot nematode solution into the wells of a 96-well plate, then add 10μL of the prepared nitrostyrene compound solution to be tested to the above solution, and cover the 96-well plate to prevent the solution from evaporating. Incubate at 25°C in the dark, and observe the death of the southern root-knot nematodes under a 40-degree stereo binocular microscope at 24h and 48h, respectively. If the body of the southern root-knot nematode is straight, or the southern root-knot nematode does not move when pricked with a strong needle, it is considered dead, otherwise it is alive.

[0040] Results: The southern root-knot nematode mortality of each compound at different concentrations was calculated based on the nematicidal bioassay data. The calculation formula is as follows:

[0041]

[0042] Three parallel experiments were set up for each concentration to determine the insecticidal rate of this type of compound. The results are shown in Table 1.

[0043] Table 1. Insecticidal rate of nitrostyrene compounds against root-knot nematodes at 50 μg / mL and 12.5 μg / mL (%) It can be seen from Table 1 that the nitrostyrene compounds involved in the present invention all show excellent insecticidal effects on southern root-knot nematodes, and the compounds show 100% inhibitory activity on southern root-knot nematodes at 50 μg / mL. At a concentration of 12.5 μg / mL, except for the lower insecticidal rate of trans-4-(2-nitrovinyl)benzonitrile to southern root-knot nematodes of 40.19%, the insecticidal rates of the remaining compounds are still 100%, and the insecticidal effects are obvious, which is worthy of further development as nematicides.

[0044] Test Example 2: Determination of the activity of nitrostyrene compounds in killing pine wood nematodes

[0045] The specific test operation method is as shown in Example 1, except that the root-knot nematode is replaced by pine wood nematode; the test results are shown in Table 2.

[0046] Table 2. Insecticidal rate of nitrostyrene compounds against pine wood nematodes at 50 μg / mL and 12.5 μg / mL (%) It can be seen from Table 2 that the series of compounds involved in the present invention all show certain insecticidal effects on pine wood nematodes. In particular, at a concentration of 50 μg / mL, except for trans-4-(2-nitrovinyl)benzonitrile, which has a relatively low insecticidal rate of 61.69% against pine wood nematodes, the remaining nitrostyrene compounds all show more than 90% inhibitory activity against pine wood nematodes. It is worth noting that at a concentration of 12.5 μg / mL, trans-4-bromo-β-nitrostyrene still shows 100% insecticidal activity against pine wood nematodes, and is worthy of further development as a nematicide.

[0047] The present invention also studies the preparation of nitrostyrene compounds, and some preparation examples are as follows:

[0048] Example 1: 20% β-nitrostyrene water dispersible granules

[0049] Components content(%) Remark β-Nitrostyrene 20 Active ingredients Sodium Lauryl Sulfate 4 Wetting Agents Sodium lignin sulfonate 1.5 First dispersant Sodium naphthalenesulfonate 2 Second dispersant Sodium carbonate 2 Disintegrants Polyvinyl alcohol 2 Binder Kaolin Make up 100 filler

[0050] The water dispersible granules are prepared by conventional methods, which can be as follows: the active ingredient, wetting agent, dispersant, disintegrant, binder and filler are weighed according to the proportion, added into a food processor and mixed evenly, then put into a jet mill for grinding, mixed again with a food processor, added with an appropriate amount of water, and extruded into granules with a granulator to obtain the water dispersible granules.

[0051] Example 2, 5% trans-nitrostyrene granules

[0052] Components content(%) Remark trans-nitrostyrene 5 Active ingredients Sodium Lauryl Sulfate 4 Wetting Agents Sodium lignin sulfonate 1.5 Dispersants Polyvinyl alcohol 2 Binder Humic acid 2 filler Kaolin Make up 100 filler

[0053] The granules are prepared by conventional methods, which can be as follows: the active ingredient, wetting agent, dispersant, binder, and carrier are weighed in a certain proportion, mixed evenly, kneaded with the binder, granulated, dried at a certain temperature for 8 minutes, and sieved to obtain the finished product.

[0054] Example 3, 2% trans-4-fluoro-β-nitrostyrene granules

[0055] Components content(%) Remark trans-4-fluoro-β-nitrostyrene 2 Active ingredients Calcium lignin sulfonate 3 Dispersants Corn starch 2 Binder fertilizer 5 filler Urea Make up 100 filler

[0056] The granules are prepared by conventional methods, which can be as follows: the active ingredient, dispersant, binder, fertilizer (N, P, K mixed in a certain proportion) and carrier are weighed in a certain proportion, mixed evenly, kneaded with the binder, granulated, dried at a certain temperature for 8 minutes, and sieved to obtain the finished product.

[0057] Example 4: 50% trans-4-bromo-β-nitrostyrene aqueous suspension

[0058] Components content(%) Remark trans-4-bromo-β-nitrostyrene 50 Active ingredients Castor Oil Polyoxyethylene Ether 3.2 Wetting Agents Polyacrylic acid 2 First dispersant Glyceryl fatty acid ester polyoxyethylene ether 1.5 Second dispersant Ethylene glycol 2 antifreeze Xanthan gum 1 First thickener Magnesium Aluminum Silicate 1 Second thickener Casson 1 preservative Silicone 0.5 Defoaming agent Deionized water Make up 100 Carrier

[0059] The suspension is prepared by conventional methods, which can be as follows: Weigh the wetting agent, dispersant, antifreeze, preservative, defoamer, and deionized water according to the ratio, add them into a beaker and mix them evenly, then add compound Mb-1 into the beaker, and then transfer it to a sand mill, add zirconium oxide beads into the sand mill, grind for 2-3 hours, add thickener xanthan gum and magnesium aluminum silicate, and continue grinding for 0.5 hours to make the particle size D 95 The product can be obtained by controlling the particle size below 5 microns and filtering to remove the zirconium oxide beads.

[0060] Example 5, 10% trans-4-bromo-β-nitrostyrene microcapsule suspension

[0061]

[0062]

[0063] The microcapsule suspension is prepared according to a conventional method, which can be as follows: trans-4-bromo-β-nitrostyrene is completely dissolved in vegetable oil and solvent oil S-150 to obtain an oil phase; polyvinyl alcohol, lignin sulfonate, and styrylphenol polyoxyethylene polyoxypropylene ether are added to water and stirred evenly to obtain an aqueous phase; the aqueous phase is poured into the oil phase, stirred at a speed of 1200 rpm to form a stable oil-in-water emulsion, the rotation speed is reduced to 600 rpm, melamine formaldehyde resin is added to solidify the capsule wall material into capsules, and after the capsule material is completely solidified, hydrochloric acid is added to adjust the pH to 6-6.5, and magnesium aluminum silicate is added, and stirred evenly to prepare a 10% trans-4-bromo-β-nitrostyrene microcapsule suspension.

[0064] Example 6, 30% 4-methoxy-β-nitrostyrene wettable powder

[0065] Components content(%) Remark 4-Methoxy-β-nitrostyrene 30 Active ingredients Sodium Lauryl Sulfate 3 Wetting Agents Sodium Methylene Bisnaphthalene Sulfonate 2 Dispersants White Carbon Black 2 filler Kaolin Make up 100 filler

[0066] The wettable powder is prepared by conventional methods, which can be as follows: the active ingredient, wetting agent, dispersant and filler are weighed according to the proportion, added into a food processor and mixed evenly, and then put into a jet mill for pulverization.

[0067] Example 7, 10% 1-(3-fluorophenyl)-2-nitroethylene aqueous suspension

[0068]

[0069]

[0070] The suspension was prepared by conventional methods.

[0071] Example 8, 1% (E)-1-fluoro-2-(2-nitrovinyl)benzene granules

[0072] Components content(%) Remark (E)-1-Fluoro-2-(2-nitrovinyl)benzene 1 Active ingredients Sodium Lauryl Sulfate (K12) 1 Wetting Agents Alkylbenzene sulfonate 1.6 Wetting Agents 2-Naphthalenesulfonic acid formaldehyde polymer sodium salt 2 Dispersants starch 1 Binder fertilizer 10 Carrier Borax Make up 100 Carrier

[0073] The granules are prepared by conventional methods, which can be as follows: the active ingredient, dispersant, binder, fertilizer (N, P, K mixed in a certain proportion) and carrier are weighed in a certain proportion, mixed evenly, kneaded with the binder, granulated, dried at a certain temperature for 8 minutes, and sieved to obtain the finished product.

[0074] Test Example 3: Efficacy test for controlling southern root-knot nematodes in tomatoes

[0075] Test reagents:

[0076] Example 1: 20% β-nitrostyrene water dispersible granules;

[0077] Example 2: 5% trans-nitrostyrene granules

[0078] Example 3: 2% trans-4-fluoro-β-nitrostyrene granules

[0079] Example 5: 10% trans-4-bromo-β-nitrostyrene microcapsule suspension

[0080] Example 6: 30% 4-methoxy-β-nitrostyrene wettable powder

[0081] Example 7: 10% 1-(3-fluorophenyl)-2-nitroethylene suspension

[0082] Example 8: 1% (E)-1-fluoro-2-(2-nitrovinyl)benzene granules

[0083] Control agent: 0.5% avermectin granules, registration certificate PD20140479, Sarfu (Henan) Agrochemical Co., Ltd., purchased from the market; 3000-3500 g / mu

[0084] 41.7% Fluopyram suspension, registration certificate PD20121664, Bayer AG, commercially available. 0.024-0.030 ml / plant, root irrigation

[0085] Test method:

[0086] The experiment was conducted in the greenhouse of Guangxi Tianyuan Biochemical Co., Ltd. Each pot was filled with 5 kg of soil infected with southern root-knot nematodes. After mixing with other soil, it was placed in a flower pot with a diameter of 30 cm and a height of 25 cm. When the tomato seedlings grew 3 true leaves, they were moved into the pot (3 plants / pot). After the seedlings were planted and survived, the pesticides were applied around the plants. The experiment was designed for a total of 9 treatments, 4 pots in each treatment, and 4 replicates. The amount of pesticide applied in each pot was converted according to the area. The granular pesticide was mixed with the soil and spread, and the liquid pesticide was watered with water. Each potted tomato seedling in each treatment was uniformly watered to keep the soil moist. Daily unified fertilizer and water management, no more pesticides were applied. The plants were observed from time to time for any drug efficacy. 60 days after the drug was applied, all the roots of the tomato plants were dug out and washed with clean water. The degree of root invasion of the plants was investigated, and the root knot index was calculated.

[0087] Disease severity grading standards: Gall. index (GI) refers to the number of root knots formed by root-knot nematodes on the root system; Egg mass index (Eggmass) refers to the number of egg masses of root-knot nematodes on the root system. The grading standards for root-knot nematode disease are: Grade 0 (no root knots); Grade 1 (1%-15% of the roots have root knots); Grade 2 (16%-25% of the roots have root knots); Grade 3 (26%-50% of the roots have root knots); Grade 4 (51%-75% of the roots have root knots); Grade 5 (more than 76% of the roots have root knots).

[0088] The calculation formula is: disease index (%) = ∑ (number of plants at each level × level) / (total number of plants surveyed × 5) × 100.

[0089] Control effect (%) = (control disease index - treatment disease index) / control disease index × 100

[0090] The results are shown in Table 4.

[0091] Table 4. Control effect of various pesticides on southern root-knot nematodes of tomatoes

[0092]

[0093] As shown in Table 4, the protective effects of nitrostyrene compounds against southern root-knot nematodes of tomatoes are significantly better than the control agent 0.5% avermectin granules, and they have the prospect of being further developed as agricultural fungicides.

[0094] In summary, the nitrostyrene compounds of the present invention exhibit good insecticidal activity against root-knot nematodes and pine wood nematodes, and are worthy of further research and development in agriculture.

[0095] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit it. Although the present invention has been described in detail with reference to the aforementioned embodiments, those skilled in the art should understand that they can still modify the technical solutions described in the aforementioned embodiments, or make equivalent replacements for some of the technical features therein. However, these modifications or replacements do not deviate the essence of the corresponding technical solutions from the spirit and scope of the technical solutions of the embodiments of the present invention.

Claims

1. Application of nitrostyrene compounds in preventing, controlling or resisting plant pathogenic nematodes.

2. Use of preparations containing nitrostyrene compounds in preventing, controlling or resisting plant pathogenic nematodes.

3. The use according to claim 1 or 2, characterized in that: The nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, trans-4-(2-nitrovinyl)benzonitrile, 1-(3-fluorophenyl)-2-nitrovinyl, and (E)-1-fluoro-2-(2-nitrovinyl)benzene; wherein the chemical structural formula of each nitrostyrene compound is as follows:

4. The use according to any one of claims 1 to 3, characterized in that: The pathogenic nematodes include at least one of root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes; Optionally, the pathogenic nematodes include root-knot nematodes, and the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, 1-(3-fluorophenyl)-2-nitrobenzene, and (E)-1-fluoro-2-(2-nitrovinyl)benzene; Optionally, the pathogenic nematodes include pine wood nematodes, and the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, 1-(3-fluorophenyl)-2-nitrobenzene, and (E)-1-fluoro-2-(2-nitrovinyl)benzene; optionally, the nitrostyrene compound includes trans-4-bromo-β-nitrostyrene.

5. The use according to any one of claims 1 to 4, characterized in that: The dosage form of the nitrostyrene compound is one or more of granules, dry suspensions, water suspensions, dispersible oil suspensions, microcapsule suspensions, wettable powders, emulsifiable concentrates, water emulsions, water dispersible granules, and seed treatment agents; Optionally, the preparation of the nitrostyrene compound preparation also includes an auxiliary agent, and the auxiliary agent is selected from one or more of a dispersant, a wetting agent, a filler, an emulsifier, a thickener, a dispersion medium, a disintegrant, a solvent, a preservative, an antifreeze agent, a specific gravity regulator, a defoaming agent, an oil phase wall material, an aqueous phase wall material, and water.

6. An insecticide containing nitrostyrene compounds for preventing, controlling or resisting plant pathogenic nematodes, characterized in that: It contains nitrostyrene compounds and agriculturally acceptable adjuvants; Optionally, the nitrostyrene compound is selected from one or more of β-nitrostyrene, trans-nitrostyrene, trans-4-fluoro-β-nitrostyrene, trans-4-bromo-β-nitrostyrene, 4-methoxy-β-nitrostyrene, trans-4-(2-nitrovinyl)benzonitrile, 1-(3-fluorophenyl)-2-nitrovinyl, (E)-1-fluoro-2-(2-nitrovinyl)benzene; wherein the chemical structural formula of each nitrostyrene compound is as follows:

7. The insecticide according to claim 6, characterized in that The dosage form of the insecticide is one or more of granules, dry suspensions, water suspensions, dispersible oil suspensions, microcapsule suspensions, wettable powders, emulsifiable concentrates, water emulsions, water dispersible granules, and seed treatment agents; Optionally, the agriculturally acceptable adjuvant is selected from one or more of synergists, dispersants, wetting agents, fillers, emulsifiers, thickeners, dispersion media, disintegrants, solvents, preservatives, antifreeze agents, specific gravity regulators, defoamers, oil phase wall materials, water phase wall materials, and water; Optionally, it also includes one or more of commercial insecticides, miticides, fungicides, anti-plant virus agents and plant activators; Optionally, the pathogenic nematodes include at least one of root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes.

8. The insecticide according to claim 6 or 7, characterized in that The dosage form of the insecticide is a granule, which includes the following raw materials in parts by weight: 1-20 parts of nitrostyrene compounds, 3-4 parts of wetting agents, 1.5-3.5 parts of dispersants, 0.2-3 parts of disintegrants, 0.2-3 parts of binders, and 68.5-93 parts of fillers; optionally, it includes the following raw materials in parts by weight: 5-20 parts of nitrostyrene compounds, 4 parts of wetting agents, 1.5-3.5 parts of dispersants, 2 parts of disintegrants, 2 parts of binders, and 68.5-85.5 parts of fillers; Alternatively, the pesticide is in the form of an aqueous suspension, which comprises the following raw materials in parts by weight: 2 to 50 parts of nitrostyrene compounds, 3 to 5 parts of wetting agents, 1 to 3.5 parts of dispersants, 0 to 2 parts of antifreeze agents, 0 to 2 parts of thickeners, 0 to 2 parts of preservatives, 0.1 to 1 parts of defoaming agents, and 37.8 to 90 parts of water; Alternatively, the formulation of the insecticide is a microcapsule suspension, which includes the following raw materials in parts by weight: 2 to 10 parts of nitrostyrene compounds, 10 to 20 parts of oily solvents, 1.5 to 3 parts of dispersants, 3 to 6 parts of wetting agents, 1 to 2 parts of binders, 3 parts of capsule wall materials, 0 to 2 parts of thickeners, 0.1 to 1 parts of defoaming agents, and 63 to 80 parts of water; Alternatively, the dosage form of the insecticide is a wettable powder, which includes the following raw materials in parts by weight: 20 to 40 parts of nitrostyrene compounds, 1 to 3 parts of dispersants, 3 to 8 parts of wetting agents, and 50 to 80 parts of fillers; optionally, it includes the following raw materials in parts by weight: 30 to 40 parts of nitrostyrene compounds, 1 to 3 parts of dispersants, 3 to 8 parts of wetting agents, and 50 to 63 parts of fillers.

9. A method for reducing browning caused by plant pathogenic nematode pests, characterized in that: The pesticide according to claim 7 or 8 is diluted and sprayed or mixed and spread on the soil or plant rhizomes to be treated; optionally, the pathogenic nematodes include at least one of root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes.

10. A method for using the insecticide according to claim 7 or 8, characterized in that: The pesticide according to claim 7 or 8 is diluted and sprayed or mixed and spread on the soil or plant rhizomes to be treated, and the dosage of the active ingredient is 10-18 g / mu; optionally, the pathogenic nematodes include at least one of root-knot nematodes and pine wood nematodes; optionally, the root-knot nematodes include southern root-knot nematodes.

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