Preparation method and application of compound containing maleimide structure

Abstract

The invention relates to a preparation method of a compound containing a maleimide structure, the structural formula of the compound is as shown in formula I. The preparation method comprises the following steps: adding substituted aniline and sodium hydrogen sulfate into a container containing maleic anhydride under the condition of high-temperature stirring, fully reacting, treating, and further purifying to obtain the compound containing the maleimide structure, the compound containing the maleimide structure has high biological activity on soil-borne pathogenic fungi and nematodes, can be widely used for prevention and treatment of soil-borne diseases, and provides material guarantee for safe production of crops. # imgabs0 #

Description

Technical Field

[0001] The present invention belongs to the technical field of agricultural chemicals, and in particular relates to a preparation method and application of a compound containing a maleimide structure. Background Art

[0002] Soilborne diseases are caused by pathogens (fungi, nematodes, and protozoa, etc.) that spend most of their life cycle in the soil and infect the roots and stems of plants under suitable conditions. Due to the intensive planting and single continuous cropping production models of modern agriculture, pathogens in the soil accumulate year by year, and soilborne diseases have become a major factor restricting the sustainable development of agriculture. The most economical and effective way to prevent and control soilborne diseases is to use chemical agents. However, traditional agents for controlling soilborne diseases, such as chloropicrin, calcium cyanamide, dazomethane, sulfuryl fluoride, 1,3-dichloropropylene, dimethyl disulfide, methamphetamine, and methyl bromide, are highly toxic to non-target organisms, easily cause damage to the environment, and the repeated use of a single agent leads to increasingly serious resistance. Therefore, the development of efficient, safe, and structurally novel compounds to control soilborne diseases has become an urgent need for sustainable agricultural production.

[0003] Maleimide derivatives are five-membered ring compounds belonging to the cyclic imide class. They possess excellent antimicrobial activity with high selectivity and specificity. Therefore, they are widely used in the prevention and treatment of soil-borne diseases, providing a material guarantee for safe crop production.

[0004] A reported method for preparing imine compounds by reacting substituted aniline with maleic anhydride involves dissolving maleic anhydride in acetic acid, adding the substituted aniline, heating the mixture to 115-130°C, stirring for 3-5 hours, and then cooling to room temperature. The precipitated solid product is washed and filtered to obtain the final product (Patent Document 1: Pest Management Science, 2015, 3, 71: 433-440). Due to the low solubility of maleic anhydride and substituted aniline in acetic acid, this method requires the use of a large amount of acetic acid, which not only wastes resources but also poses safety risks to the environment and human health. To reduce the environmental pollution caused by organic solvents, a solvent-free melt method has been developed for preparing imine compounds. Specifically, maleic anhydride and aniline react at 140-200°C using zinc chloride or tin chloride as a catalyst to produce the imine compound (Patent Document 2: Progress in Fine Petrochemicals, 2000, 8, 1, 37: 1009-8348). This method has the characteristics of high yield and environmental friendliness, but it also has problems such as high product viscosity, high catalyst corrosiveness, many side reactions, and difficult post-processing.

[0005] The present invention adopts a simple and green method to prepare a series of antibacterial compounds containing maleimide structures. Summary of the Invention

[0006] To overcome the shortcomings of the aforementioned problems, the present invention provides a method for preparing compounds containing a maleimide structure. To this end, the present invention prepares a series of compounds containing a maleimide structure by reacting maleic anhydride with substituted aniline in the presence of sodium bisulfate. This method features mild reaction conditions, high catalytic efficiency, the absence of solvents, and easy catalyst recovery, resulting in low production costs and a safe, environmentally friendly process.

[0007] This type of compound has high biological activity against soil-borne pathogenic fungi and nematodes, and can be widely used in the prevention and control of soil-borne diseases, providing material guarantee for safe crop production.

[0008] The present invention provides a method for preparing a compound containing a maleimide structure, wherein the molecular structure of the compound is shown in the following formula I:

[0009]

[0010] Wherein, R is phenyl or substituted phenyl, and the substituted phenyl is alkylphenyl, halogenated phenyl, halogenated nitrophenyl, alkylhalogenated phenyl, nitrophenyl, or alkylnitrophenyl, wherein,

[0011] Phenyl Alkylphenyl is Halogenated phenyl is

[0012]

[0013]

[0014]

[0015] Halogenated nitrophenyl

[0016]

[0017] Alkyl halophenyl is

[0018]

[0019]

[0020] Nitrophenyl Alkyl nitrophenyl

[0021]

[0022] The specific steps are as follows:

[0023] A certain amount of maleic anhydride, substituted aniline and sodium bisulfate as a catalyst are sequentially added to a reaction vessel, and reacted under high temperature stirring; thin layer chromatography is used to track the reaction progress, and the reaction product is post-treated at the reaction endpoint to purify and obtain a compound containing a maleimide structure.

[0024] Wherein, the substituted aniline added in the above reaction is selected from one of aniline, alkylaniline, halogenated aniline, halogenated nitroaniline, alkylnitroaniline, nitroaniline or alkylnitroaniline, wherein the alkylaniline is p-methylaniline, and the halogenated aniline is p-chloroaniline, 2,4-dichloroaniline, 3,5-dichloroaniline, m-chloroaniline, 2,5-dichloroaniline, 2-chloro-4-bromoaniline, 2,4,6-trichloroaniline, 3,4-dichloroaniline, 2-chloro-4-iodoaniline, 2,6-dichloroaniline, 2-chloro-6-fluoroaniline, 2,3-dichloroaniline, 2,4,5-trichloroaniline, 2-chloro-3-fluoroaniline, 2-chloro-4- Fluoroaniline, 3-chloro-5-fluoroaniline, 2,6-dichloro-4-fluoroaniline, m-fluoroaniline, p-fluoroaniline, 2,6-difluoro-4-bromoaniline, 2-fluoro-5-bromoaniline, 2-fluoro-4-chloroaniline, 2-fluoro-5-chloroaniline, 2-fluoro-3-chloroaniline, 3-fluoro-4-chloroaniline, 2-fluoro-5-nitroaniline, 3,5-difluoroaniline, 2,3,6-trifluoroaniline, 2-fluoro-4-iodoaniline, 3-fluoro-4-bromoaniline, 3,4,5-trifluoroaniline, 3,4-difluoroaniline, 2,3,4-trifluoroaniline, 2,3-difluoroaniline, 2-fluoro-4-bromoaniline, 2,5-difluoroaniline, 2,4,6- Trifluoroaniline, 2,4,5-trifluoroaniline, 2,6-difluoro-4-bromoaniline, 2,3,5-trifluoroaniline, m-iodoaniline, p-iodoaniline, 2-iodo-5-chloroaniline, 2-iodo-4-fluoroaniline, 2,5-diiodoaniline, o-iodoaniline, 2-iodo-4-bromoaniline, 3-fluoro-5-bromoaniline, 3,5-difluoro-4-iodoaniline, 2,6-difluoro-4-iodoaniline, 3-iodo-4-bromoaniline, 3-iodo-4-fluoroaniline, 2,6-diiodo-4-bromoaniline, 2-iodo-5-fluoroaniline, 3-bromo-5-iodoaniline, 3-iodo-4-chloroaniline, 2-iodo-4-chloroaniline, 2,4,6-triiodoaniline, m-iodoaniline, Bromoaniline, p-bromoaniline, o-bromoaniline, 2-bromo-5-fluoroaniline, 2-bromo-4-chloroaniline, 2,6-dibromo-4-fluoroaniline, 2-bromo-4-fluoroaniline, 3,5-dibromoaniline, 2,4-dibromoaniline, 2,5-dibromoaniline, 2,6-dibromoaniline, 2,4,6-tribromoaniline, 3-bromo-5-fluoroaniline, 3-bromo-4-fluoroaniline; the halogenated nitroaniline is 4,5-dichloro-2-nitroaniline, 2-chloro-4-nitroaniline, 2-chloro-5-nitroaniline, 2-nitro-4,5-dichloroaniline, 3-nitro-4-bromoaniline, 2-nitro-4-bromoaniline, 2-fluoro-6-nitroaniline;The alkyl haloaniline is 2-chloro-6-methylaniline, 2-chloro-4-methylaniline, 3-chloro-4-methylaniline, 2,4-dichloro-3-methylaniline, 2,4-dichloro-6-methylaniline, 2-methyl-5-chloroaniline, 2-methyl-4-chloroaniline, 3-methyl-4-chloroaniline, 2,5-dimethyl-4-chloroaniline, 2-methyl-3-fluoroaniline, 2-methyl-4-fluoroaniline, 3-methyl-4-fluoroaniline, 3-fluoro-4-methylaniline, 2-fluoro-6-methylaniline, 2-fluoro-4-methylaniline, 2-fluoro-5-methylaniline, 2-fluoro-3-methylaniline, 2-iodo-5-methylaniline, 3-iodo-4-methylaniline, 2-iodo-3-methylaniline, 2-iodo-6-methylaniline, 2 ,4-diiodo-6-methylaniline, 2-iodo-4,5-dimethylaniline, 2-iodo-4,6-dimethylaniline, 2-iodo-4,5-dimethylaniline, 2-bromo-3-methylaniline, 2-bromo-6-methylaniline, 2-bromo-4-methylaniline, 2,6-dibromo-4-methylaniline, 2-bromo-4,6-dimethylaniline, 2-bromo-4-methylaniline; the nitroaniline is p-nitroaniline, 2,5-dinitroaniline, 2,4-dinitroaniline, m-nitroaniline; the alkyl nitroaniline is 2-methyl-3-nitroaniline, 2-methyl-5-nitroaniline, 3-nitro-4-methylaniline, 2-nitro-6-methylaniline, 2-nitro-4-methylaniline, 2-nitro-4,5-dimethylaniline;

[0025] Among the above-mentioned substituted anilines, halogenated anilines and halogenated nitroanilines are preferred, and p-chloroaniline, 2,4-dichloroaniline, 3,5-dichloroaniline, 3,4-dichloroaniline, 2-chloro-4-nitroaniline, and 2-chloro-5-nitroaniline are more preferred.

[0026] The molar ratio of substituted aniline to maleic anhydride is 1.0:1.1-2.0, preferably 1.0:1.1-1.5; the amount of catalyst used accounts for 0.3%-1% of the total reaction system, preferably 0.3%-0.8%; the reaction temperature is 80-150° C., preferably 90-140° C.; and the reaction time is 0.5-4.0 h, preferably 1-3.5 h.

[0027] In one application, the compound containing a maleimide structure obtained by the present invention is used in controlling soil-borne Botrytis cinera Pers, Sclerotinia sclerotiorum, Fusarium graminearum and southern root-knot nematode Meloidogyne incognita.

[0028] Beneficial effects

[0029] According to the preparation method of the present invention, 1) sodium bisulfate is used as a catalyst, the reaction conditions are mild, the catalytic efficiency is high, and since no solvent is used, the catalyst can be easily recovered. Therefore, the preparation method of the present invention is low in cost and the preparation process is safe and green;

[0030] 2) The obtained compound containing a maleimide structure has high biological activity against soil-borne pathogenic fungi and nematodes, and can be widely used in the prevention and control of soil-borne diseases, providing material guarantee for the safe production of crops.

[0031] 3) During the experimental process of preparing the compound containing a maleimide structure, sodium bisulfate and excess maleic anhydride are recovered by centrifugation and filtration and used in the next round of preparing the compound containing a maleimide structure (so-called recycling), thereby fully recycling the raw materials, thereby reducing the preparation cost and improving safety. DETAILED DESCRIPTION

[0032] The following uses specific embodiments to describe in detail the implementation methods of the present invention, so that the implementation process of how the present invention applies technical means to solve technical problems and achieve technical effects can be fully understood and implemented accordingly.

[0033] In the following examples, the chemical reagents used are commercial industrial pure products, and the equipment used is well known in the art.

[0034] Example 1

[0035] 1.08 g (11.0 mmol) of maleic anhydride, 0.93 g (10.0 mmol) of aniline and 0.006 g of sodium bisulfate were added to a 10 mL beaker and stirred at 80°C. The reaction progress was monitored by thin layer chromatography. After 4.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.5% and a yield of 92.63%. The structural formula of the product is (I-1). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.23 to 7.46 ppm were peaks at the benzene ring (CH), and 7.15 ppm were peaks at the imide ring (CH=CH).

[0036]

[0037] Example 2

[0038] 1.47 g (15.0 mmol) of maleic anhydride, 1.28 g (10.0 mmol) of p-chloroaniline and 0.01 g of sodium bisulfate were added to a 10 mL beaker and stirred at 90°C. The reaction progress was monitored by thin layer chromatography. After 4.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.2% and a yield of 85.23%. The structural formula of the product is (I-2). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.38 to 7.58 ppm was a peak at the benzene ring (CH), and 7.22 ppm was a peak at the imide ring (CH=CH).

[0039]

[0040] Example 3

[0041] 1.96g (20.0mmol) of maleic anhydride, 1.62g (10.0mmol) of 2,4-dichloroaniline and 0.018g of sodium bisulfate were added to a 10mL beaker, stirred at 100°C, and the reaction progress was monitored by thin layer chromatography. After 3.0h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 98.1% and the yield was 86.13%. The structural formula of the product was (I-3). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.48 to 8.03 ppm was a peak at the benzene ring (CH), and 7.20 ppm was a peak at the imide ring (CH=CH).

[0042]

[0043] Example 4

[0044] 1.96g (20.0mmol) of maleic anhydride, 1.62g (10.0mmol) of 3,5-dichloroaniline and 0.021g of sodium bisulfate were added to a 10mL beaker, stirred at 110°C, and the reaction progress was monitored by thin layer chromatography. After 3.0h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 99.3% and the yield was 90.31%. The structural formula of the product was (I-4). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.25 to 7.72 ppm was a peak at the benzene ring (CH), and 7.14 ppm was a peak at the imide ring (CH=CH).

[0045]

[0046] Example 5

[0047] 1.96g (20.0mmol) of maleic anhydride, 1.62g (10.0mmol) of 3,4-dichloroaniline and 0.025g of sodium bisulfate were added to a 10mL beaker, stirred at 120°C, and the reaction progress was monitored by thin layer chromatography. After 2.5h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 98.4% and the yield was 89.11%. The structural formula of the product was (I-5). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.33 to 7.85 ppm was a peak at the benzene ring (CH), and 7.21 ppm was a peak at the imide ring (CH=CH).

[0048]

[0049] Example 6

[0050] 1.96g (20.0mmol) of maleic anhydride, 2.95g (10.0mmol) of 2,4,6-trichloroaniline and 0.028g of sodium bisulfate were added to a 10mL beaker, stirred at 130°C, and the reaction progress was monitored by thin layer chromatography. After 2.0h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 96.1% and a yield of 79.32%. The structural formula of the product is (I-6). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.69 ppm was a peak at the benzene ring (CH), and 7.43 ppm was a peak at the imide ring (CH=CH).

[0051]

[0052] Example 7

[0053] 1.57 g (16.0 mmol) of maleic anhydride, 1.41 g (10.0 mmol) of 2-chloro-5-methylaniline and 0.028 g of sodium bisulfate were added to a 10 mL beaker and stirred at 140°C. The reaction progress was monitored by thin layer chromatography. After 1.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 97.8% and a yield of 87.35%. The structural formula of the product is (I-7). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 2.18 ppm was a peak at CH3, 6.93 to 7.49 ppm were peaks at the benzene ring (CH), and 7.16 ppm was a peak at the imide ring (CH=CH).

[0054]

[0055] Example 8

[0056] 1.96 g (20.0 mmol) of maleic anhydride, 2.06 g (10.0 mmol) of 2-chloro-5-bromoaniline and 0.032 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C. The reaction progress was monitored by thin layer chromatography. After 1.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 97.6% and a yield of 85.47%. The structural formula of the product is (I-8). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.43 to 7.91 ppm were peaks at the benzene ring (CH), and 7.25 ppm were peaks at the imide ring (CH=CH).

[0057]

[0058] Example 9

[0059] 1.96 g (20.0 mmol) of maleic anhydride, 2.53 g (10.0 mmol) of 2-chloro-4-iodoaniline and 0.045 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C. The reaction progress was monitored by thin layer chromatography. After 0.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 99.3% and a yield of 90.46%. The structural formula of the product is (I-9). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.15 to 7.82 ppm was a peak at the benzene ring (CH), and 6.93 ppm was a peak at the imide ring (CH=CH).

[0060]

[0061] Example 10

[0062] 1.47 g (15.0 mmol) of maleic anhydride, 1.45 g (10.0 mmol) of 2-chloro-6-fluoroaniline and 0.009 g of sodium bisulfate were added to a 10 mL beaker and stirred at 120°C. The reaction progress was monitored by thin layer chromatography. After 3.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 99.3% and a yield of 91.27%. The structural formula of the product is (I-10). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.53 to 7.96 ppm was a peak at the benzene ring (CH), and 7.26 ppm was a peak at the imide ring (CH=CH).

[0063]

[0064] Example 11

[0065] 1.47 g (15.0 mmol) of maleic anhydride, 1.38 g (10.0 mmol) of p-nitroaniline and 0.011 g of sodium bisulfate were added to a 10 mL beaker and stirred at 110°C. The reaction progress was monitored by thin layer chromatography. After 3.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.5% and a yield of 87.83%. The structural formula of the product is (I-11). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.81 to 8.42 ppm were peaks at the benzene ring (CH), and 7.35 ppm were peaks at the imide ring (CH=CH).

[0066]

[0067] Example 12

[0068] 1.96g (20.0mmol) of maleic anhydride, 1.83g (10.0mmol) of 3,5-dinitroaniline and 0.019g of sodium bisulfate were added to a 10mL beaker, stirred at 100°C, and the reaction progress was monitored by thin layer chromatography. After 3.0h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 98.7% and the yield was 85.38%. The structural formula of the product was (I-12). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 8.57 to 8.99 ppm was a peak at the benzene ring (CH), and 7.28 ppm was a peak at the imide ring (CH=CH).

[0069]

[0070] Example 13

[0071] 1.96g (20.0mmol) of maleic anhydride, 1.83g (10.0mmol) of 2,4-dinitroaniline and 0.023g of sodium bisulfate were added to a 10mL beaker, stirred at 90°C, and the reaction progress was monitored by thin layer chromatography. After 3.5h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 96.5% and the yield was 79.23%. The structural formula of the product was (I-13). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 8.17 to 9.06 ppm was a peak at the benzene ring (CH), and 7.38 ppm was a peak at the imide ring (CH=CH).

[0072]

[0073] Example 14

[0074] 1.57 g (16.0 mmol) of maleic anhydride, 1.38 g (10.0 mmol) of m-nitroaniline and 0.021 g of sodium bisulfate were added to a 10 mL beaker and stirred at 80°C. The reaction progress was monitored by thin layer chromatography. After 4.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 97.2% and a yield of 86.41%. The structural formula of the product is (I-14). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 8.02 to 8.47 ppm were peaks at the benzene ring (CH), and 7.43 ppm were peaks at the imide ring (CH=CH).

[0075]

[0076] Example 15

[0077] 1.96 g (20.0 mmol) of maleic anhydride, 2.17 g (10.0 mmol) of 2-nitro-4-bromoaniline and 0.033 g of sodium bisulfate were added to a 10 mL beaker and stirred at 130°C. The reaction progress was monitored by thin layer chromatography. After 2.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 96.9% and a yield of 75.25%. The structural formula of the product is (I-15). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.82 to 8.39 ppm was a peak at the benzene ring (CH), and 7.41 ppm was a peak at the imide ring (CH=CH).

[0078]

[0079] Example 16

[0080] 1.96 g (20.0 mmol) of maleic anhydride, 1.56 g (10.0 mmol) of 2-fluoro-6-nitroaniline and 0.032 g of sodium bisulfate were added to a 10 mL beaker and stirred at 140°C. The reaction progress was monitored by thin layer chromatography. After 1.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.3% and a yield of 87.37%. The structural formula of the product is (I-16). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.57 to 8.24 ppm was a peak at the benzene ring (CH), and 7.25 ppm was a peak at the imide ring (CH=CH).

[0081]

[0082] Example 17

[0083] 1.47 g (15.0 mmol) of maleic anhydride, 1.11 g (10.0 mmol) of 3-fluoroaniline and 0.026 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C for reaction. The reaction progress was monitored by thin layer chromatography. After 0.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 99.1% and a yield of 91.05%. The structural formula of the product is (I-17). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.27 to 7.64 ppm was a peak at the benzene ring (CH), and 7.08 ppm was a peak at the imide ring (CH=CH).

[0084]

[0085] Example 18

[0086] 1.76 g (18.0 mmol) of maleic anhydride, 1.11 g (10.0 mmol) of p-fluoroaniline and 0.009 g of sodium bisulfate were added to a 10 mL beaker, stirred at 80°C, and the reaction progress was monitored by thin layer chromatography. After 4.0 h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product was obtained with a content of 98.6% and a yield of 90.74%. The structural formula of the product is (I-18). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.30 to 7.46 ppm was a peak at the benzene ring (CH), and 7.11 ppm was a peak at the imide ring (CH=CH).

[0087]

[0088] Example 19

[0089] 1.76g (18.0mmol) of maleic anhydride, 1.29g (10.0mmol) of 3,5-difluoroaniline and 0.012g of sodium bisulfate were added to a 10mL beaker, stirred at 90°C, and the reaction progress was tracked by thin layer chromatography. After 4.0h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 98.1% and the yield was 87.25%. The structural formula of the product was (I-19). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 6.71 to 7.10 ppm was a peak at the benzene ring (CH), and 6.83 ppm was a peak at the imide ring (CH=CH).

[0090]

[0091] Example 20

[0092] 1.37 g (14.0 mmol) of maleic anhydride, 1.29 g (10.0 mmol) of 3,4-difluoroaniline and 0.016 g of sodium bisulfate were added to a 10 mL beaker, stirred at 100 ° C, and the reaction progress was monitored by thin layer chromatography. After 3.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.3% and a yield of 86.11%. The structural formula of the product is (I-20). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.14 to 7.51 ppm were peaks at the benzene ring (CH), and 7.36 ppm were peaks at the imide ring (CH=CH).

[0093]

[0094] Example 21

[0095] 1.96g (20.0mmol) of maleic anhydride, 1.47g (10.0mmol) of 2,4,6-trifluoroaniline and 0.016g of sodium bisulfate were added to a 10mL beaker, stirred at 110°C, and the reaction progress was monitored by thin layer chromatography. After 2.5h of reaction, the mixture was dissolved in ethyl acetate, centrifuged and recovered by sodium bisulfate and excess maleic anhydride, and then washed three times with deionized water. After filtration and drying, the product content was 99.2% and the yield was 90.63%. The structural formula of the product was (I-21). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.13 ppm was a peak at the benzene ring (CH), and 7.25 ppm was a peak at the imide ring (CH=CH).

[0096]

[0097] Example 22

[0098] 1.76 g (18.0 mmol) of maleic anhydride, 1.46 g (10.0 mmol) of 2-fluoro-5-chloroaniline and 0.019 g of sodium bisulfate were added to a 10 mL beaker and stirred at 120°C. The reaction progress was monitored by thin layer chromatography. After 2.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.5% and a yield of 81.27%. The structural formula of the product is (I-22). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.21 to 7.97 ppm were peaks at the benzene ring (CH), and 7.32 ppm were peaks at the imide ring (CH=CH).

[0099]

[0100] Example 23

[0101] 1.96 g (20.0 mmol) of maleic anhydride, 1.90 g (10.0 mmol) of 3-fluoro-4-bromoaniline and 0.027 g of sodium bisulfate were added to a 10 mL beaker and stirred at 130°C. The reaction progress was monitored by thin layer chromatography. After 1.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.3% and a yield of 82.74%. The structural formula of the product is (I-23). ​​The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.22 to 7.85 ppm was a peak at the benzene ring (CH), and 7.19 ppm was a peak at the imide ring (CH=CH).

[0102]

[0103] Example 24

[0104] 1.96 g (20.0 mmol) of maleic anhydride, 1.72 g (10.0 mmol) of m-bromoaniline and 0.029 g of sodium bisulfate were added to a 10 mL beaker and stirred at 140°C. The reaction progress was monitored by thin layer chromatography. After 1.0 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 97.7% and a yield of 81.75%. The structural formula of the product is (I-24). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.19 to 7.65 ppm was a peak at the benzene ring (CH), and 7.16 ppm was a peak at the imide ring (CH=CH).

[0105]

[0106] Example 25

[0107] 1.96 g (20.0 mmol) of maleic anhydride, 1.72 g (10.0 mmol) of p-bromoaniline and 0.037 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C. The reaction progress was monitored by thin layer chromatography. After 0.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.9% and a yield of 87.83%. The structural formula of the product is (I-25). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.52 to 7.68 ppm was a peak at the benzene ring (CH), and 7.34 ppm was a peak at the imide ring (CH=CH).

[0108]

[0109] Example 26

[0110] 1.96 g (20.0 mmol) of maleic anhydride, 1.90 g (10.0 mmol) of 3-bromo-5-fluoroaniline and 0.035 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C. The reaction progress was monitored by thin layer chromatography. After 0.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 98.1% and a yield of 79.85%. The structural formula of the product is (I-26). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.10 to 7.49 ppm was a peak at the benzene ring (CH), and 7.27 ppm was a peak at the imide ring (CH=CH).

[0111]

[0112] Example 27

[0113] 1.96 g (20.0 mmol) of maleic anhydride, 1.86 g (10.0 mmol) of 2-bromo-4-chloroaniline and 0.038 g of sodium bisulfate were added to a 10 mL beaker and stirred at 150°C. The reaction progress was monitored by thin layer chromatography. After 0.5 h of reaction, the mixture was dissolved in ethyl acetate, and the sodium bisulfate and excess maleic anhydride were recovered by centrifugal sedimentation and reused. The mixture was washed three times with deionized water, filtered and dried to obtain a product with a content of 97.8% and a yield of 74.34%. The structural formula of the product is (I-28). The obtained compound was characterized and identified by high performance liquid chromatography, nuclear magnetic resonance hydrogen spectrum and carbon spectrum, and the appearance, purification method and yield of the obtained compound are shown in Table 1. Among them, 1 H NMR: The (NH2) peak disappeared, 7.31 to 7.89 ppm were peaks at the benzene ring (CH), and 7.23 ppm were peaks at the imide ring (CH=CH).

[0114]

[0115] Table 1 Appearance, purification method and yield of the compounds prepared in Example

[0116]

[0117]

[0118]

[0119]

[0120] Example 28

[0121] The biological activity of the compounds of the present invention against the southern root-knot nematode (Meloidogyne incognita) was tested using a nematode soil column assay. First, 250 g of soil containing nematodes was placed into a 30 cm high empty PE tube to prepare a soil column. The compounds of the present invention were then dissolved in DMF containing 6% Tween 80 and diluted with deionized water to a concentration of 100 mg L-1. -1 , 200mg L -1 , 500mg L -1 90 mL of the compound of the present invention was added to the soil column, and each treatment was repeated three times; a DMF aqueous solution containing only Tween 80 at the same concentration was used as a blank control. The soil column was placed at room temperature (25°C) for two weeks, and the mortality was examined under a stereomicroscope. The nematode inhibition rate was calculated according to formula (1):

[0122] Inhibition rate (%) = number of nematodes in the treated soil column (individuals) / total number of nematodes in the control column (individuals) × 100% (1)

[0123] The indoor toxicity results of the compounds of the present invention against southern root-knot nematodes are shown in Table 2.

[0124] Table 2 Indoor toxicity results of the compounds of the present invention against southern root-knot nematode (Meloidogyne incognita) (100, 200, 500 mg L -1 )

[0125]

[0126]

[0127] Indoor toxicity tests of the compounds described herein against the southern root-knot nematode (Meloidogyne incognita) showed that the maleimide-containing compounds of the present invention exhibited excellent control efficacy against the southern root-knot nematode. The results indicate that, for the same compound, higher concentrations resulted in higher inhibition rates and better control efficacy, and that compounds with Cl- or F- substituents on the benzene ring exhibited the best control efficacy against the southern root-knot nematode.

[0128] Example 29

[0129] The inhibitory effect of the compounds of the present invention on Fusarium graminearum was tested using the hyphal growth rate method. The compounds of the present invention were dissolved in DMF containing 6% Tween 80 and diluted with deionized water to form a series of concentration gradient solutions. The solution was then mixed with PDA medium to prepare a drug-coated medium. A 5mm diameter cake was taken from the edge of the cultured test strain and inoculated onto the drug-coated medium. Each treatment was repeated three times. When the colony diameter of the blank control reached approximately 8cm, the colony diameter was measured using the cross-cross method, and the EC value of each agent was calculated using the DPS data processing system. 50 value.

[0130] The indoor toxicity results of the compounds of the present invention against Fusarium graminearum are shown in Table 3.

[0131] Table 3 Indoor toxicity results of the compounds of the present invention against Fusarium graminearum

[0132]

[0133] Indoor toxicity tests of the compounds of the present invention against Fusarium graminearum showed that the maleimide compounds of the present invention had a good inhibitory effect on Fusarium graminearum. Furthermore, the compounds with Cl- substituents on the benzene ring showed the best control effect against the southern root-knot nematode.

[0134] Example 30

[0135] The inhibitory effect of the compounds of the present invention on Botrytis cinerea (Botrytis cinera Pers) was tested using the hyphal growth rate method. The compounds of the present invention were dissolved in DMF containing 6% Tween 80 and diluted with deionized water to form a series of concentration gradient solutions. The solution was then mixed with PDA culture medium to prepare a drug-stripped culture medium. A 5mm diameter cake was cut from the edge of the cultured test strain and inoculated onto the stripped culture medium. Each treatment was repeated three times. When the colony diameter of the blank control reached approximately 8cm, the colony diameter was measured using the cross-cross method, and the EC value of each agent was calculated using the DPS data processing system. 50 value.

[0136] Table 4 shows the indoor toxicity results of the compounds of the present invention against Botrytis cinera Pers.

[0137] Table 4 Indoor toxicity results of the compounds of the present invention against Botrytis cinera Pers

[0138]

[0139] Indoor toxicity tests against Botrytis cinera Pers showed that the maleimide compounds of the present invention exhibited a good inhibitory effect against Botrytis cinera Pers. Furthermore, compounds with Cl-substituents on the benzene ring showed the best control effect against southern root-knot nematodes.

[0140] Example 31

[0141] The inhibitory effect of the compounds described herein on Sclerotinia sclerotiorum was tested using the hyphal growth rate method. The compounds described herein were dissolved in DMF containing 6% Tween 80 and diluted with deionized water to form a series of concentration gradient solutions. The solution was then mixed with PDA medium to prepare a drug-coated culture medium. A 5 mm diameter cake was harvested from the edge of the cultured test strain and inoculated onto the culture medium. Each treatment was repeated three times. When the colony diameter of the blank control reached approximately 8 cm, the colony diameter was measured using the cross-cross method, and the EC value of each agent was calculated using the DPS data processing system. 50 value.

[0142] Table 5 shows the indoor toxicity results of the compounds of the present invention against Sclerotinia sclerotiorum.

[0143] Table 5 Indoor toxicity results of the compounds of the present invention against Sclerotinia sclerotiorum

[0144]

[0145] Indoor toxicity assays against Sclerotinia sclerotiorum showed that the maleimide compounds of the present invention exhibited excellent inhibitory effects against the fungus. Furthermore, compounds with Cl- or F- substituents on the benzene ring showed the best control effects against the southern root-knot nematode.

[0146] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention in any other manner. Any person skilled in the art may utilize the above-disclosed technical content to modify or modify the present invention into equivalent embodiments. However, any simple modifications, equivalent variations, and modifications to the above embodiments that do not depart from the technical content of the present invention and are based on the technical essence of the present invention remain within the scope of protection of the present invention.

Claims

1. A method for preparing a compound containing a maleimide structure, wherein the compound has the structural formula shown in Formula I, in, R is phenyl, alkylphenyl, halogenated phenyl, halogenated nitrophenyl, alkylhalogenated phenyl, nitrophenyl, alkylnitrophenyl, wherein, Phenyl Alkylphenyl is Halogenated phenyl is Halogenated nitrophenyl Alkyl halophenyl is Nitrophenyl Alkyl nitrophenyl The method comprises the following steps: adding a certain amount of maleic anhydride, substituted aniline and sodium bisulfate as a catalyst into a reaction container, and reacting under high temperature stirring; tracking the reaction progress by thin layer chromatography, and performing post-treatment on the reaction product at the reaction end point to purify and obtain a compound containing an imide structure.

2. The preparation method according to claim 1, wherein the substituted aniline is selected from one of aniline, alkylaniline, halogenated aniline, nitroaniline, halogenated alkylaniline, alkylnitroaniline or halogenated nitroaniline.

3. According to the preparation method described in claim 2, the alkylaniline is p-methylaniline; the halogenated aniline is p-chloroaniline, 2,4-dichloroaniline, 3,5-dichloroaniline, m-chloroaniline, 2,5-dichloroaniline, 2-chloro-4-bromoaniline, 2,4,6-trichloroaniline, 3,4-dichloroaniline, 2-chloro-4-iodoaniline, 2,6-dichloroaniline, 2-chloro-6-fluoroaniline, 2-chloro-4-fluoroaniline, 2-chloro-3-fluoroaniline, 3-chloro-5-fluoroaniline, 2,6-dichloro-4-fluoroaniline, 2,3-dichloroaniline, 2,4,5-trichloroaniline, m-fluoroaniline, p-fluoroaniline, 2,6- Difluoro-4-bromoaniline, 2-fluoro-5-bromoaniline, 2-fluoro-4-chloroaniline, 2-fluoro-5-chloroaniline, 2-fluoro-3-chloroaniline, 3-fluoro-4-chloroaniline, 3,5-difluoroaniline, 2,3,6-trifluoroaniline, 2-fluoro-4-iodoaniline, 3-fluoro-4-bromoaniline, 3,4,5-trifluoroaniline, 3,4-difluoroaniline, 2,3,4-trifluoroaniline, 2,3-difluoroaniline, 2-fluoro-4-bromoaniline, 2,5-difluoroaniline, 2,4,6-trifluoroaniline, 2,4,5-trifluoroaniline, 3-fluoro-5-bromoaniline, 3,5-difluoro-4-iodoaniline, 2,6-difluoro -4-iodoaniline, 2,6-difluoro-4-bromoaniline, 2,3,5-trifluoroaniline, m-iodoaniline, p-iodoaniline, 2-iodo-5-chloroaniline, 2-iodo-4-fluoroaniline, 2,5-diiodoaniline, o-iodoaniline, 2-iodo-4-bromoaniline, 2,6-diiodo-4-bromoaniline, 2-iodo-5-fluoroaniline, 3-bromo-5-iodoaniline, 3-iodo-4-chloroaniline, 2-iodo-4-chloroaniline, 2,4,6-triiodoaniline, 3-iodo-4-bromoaniline, 3-iodo-4-fluoroaniline, m-bromoaniline, p-bromoaniline, o-bromoaniline, 2-bromo-5-fluoroaniline, 2-bromo-4-chloroaniline, 2,6- Dibromo-4-fluoroaniline, 2-bromo-4-fluoroaniline, 3,5-dibromoaniline, 2,4-dibromoaniline, 2,5-dibromoaniline, 2,6-dibromoaniline, 3-bromo-5-fluoroaniline, 3-bromo-4-fluoroaniline, 3-bromo-5-fluoroaniline, 3-bromo-4-fluoroaniline, 2,4,6-tribromoaniline; the halogenated nitroaniline is 2-chloro-5-nitroaniline, 4,5-dichloro-2-nitroaniline, 2-chloro-4-nitroaniline, 2-nitro-4,5-dichloroaniline, 3-nitro-4-bromoaniline, 2-nitro-4-bromoaniline, 2-fluoro-6-nitroaniline, 2-fluoro-5-nitroaniline;The alkyl haloaniline is 3-chloro-4-methylaniline, 2-chloro-6-methylaniline, 2,4-dichloro-3-methylaniline, 2,4-dichloro-6-methylaniline, 2-methyl-5-chloroaniline, 2-methyl-4-chloroaniline, 3-methyl-4-chloroaniline, 2,5-dimethyl-4-chloroaniline, 2-chloro-4-methylaniline, 2-methyl-3-fluoroaniline, 2-methyl-4-fluoroaniline, 3-methyl-4-fluoroaniline, 3-fluoro-4-methylaniline, 2-fluoro-6-methylaniline, 2-fluoro-4-methylaniline, 2-fluoro-5-chloroaniline, 2-methyl-5-chloroaniline, 2-methyl-4-chloroaniline, 3-methyl-4-chloroaniline, 2,5-dimethyl-4-chloroaniline, 2-chloro-4-methylaniline, 2-methyl-3-fluoroaniline, 2-methyl-4-fluoroaniline, 3-methyl-4-fluoroaniline, 3-fluoro-4-methylaniline, 2-fluoro-6-methylaniline, 2-fluoro-4-methylaniline, 2-fluoro-5 -methylaniline, 2-fluoro-3-methylaniline, 3-iodo-4-methylaniline, 2-iodo-3-methylaniline, 2-iodo-5-methylaniline, 2-iodo-6-methylaniline, 2,4-diiodo-6-methylaniline, 2-iodo-4,5-dimethylaniline, 2-iodo-4,6-dimethylaniline, 2-iodo-4,5-dimethylaniline, 2-bromo-3-methylaniline, 2-bromo-6-methylaniline, 2-bromo-4-methylaniline, 2,6-dibromo-4-methylaniline, 2-bromo-4,6-dimethylaniline, 2-bromo-4-methylaniline. The nitroaniline is p-nitroaniline, 2,5-dinitroaniline, 2,4-dinitroaniline, and m-nitroaniline; the alkyl nitroaniline is 2-methyl-3-nitroaniline, 2-methyl-5-nitroaniline, 3-nitro-4-methylaniline, 2-nitro-6-methylaniline, 2-nitro-4-methylaniline, and 2-nitro-4,5-dimethylaniline. ; 4. The preparation method according to claim 1, wherein the molar ratio of the substituted aniline to maleic anhydride is 1.0:1.1-2.0, the amount of the catalyst accounts for 0.13%-1% of the total amount of the reaction system, the reaction temperature is 80-150° C., and the reaction time is 0.5-4.0 h.

5. Use of the compound containing a maleimide structure according to any one of claims 1 to 4 in controlling soil-borne plant pathogenic fungi and nematodes.

6. The use according to claim 5, wherein the plant pathogenic fungi are Botrytis cinerea, Sclerotinia sclerotiorum, and Fusarium graminearum, and the nematode is Meloidogyne incognita.

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