1-(2-chloromethylphenyl)-3-arylimidazoline-2-ketone compound as well as preparation method and application thereof

Abstract

The invention discloses a 1-(2-chloromethyl phenyl)-3-aryl imidazoline-2-ketone compound and a preparation method and application thereof.According to the compound, an arylamine compound and bromoacetyl bromide serve as raw materials, triethylamine serves as an acid-binding agent, dichloroethane serves as a solvent, a 2-bromoacetyl arylamine compound is obtained through a reaction in an ice-water bath, then the 2-bromoacetyl arylamine compound is subjected to a multi-step reaction, and the 1-(2-chloromethyl phenyl)-3-aryl imidazoline-2-ketone compound is obtained. Finally, the 1-(2-chloromethyl phenyl)-3-aryl imidazoline-2-ketone compound with the bactericidal activity is prepared and obtained. The raw materials for synthesis of the compound are cheap and easy to obtain, the synthesis method is simple, meanwhile, the compound has a good inhibition effect on the activity of crop germs, especially has remarkable inhibition activity on sclerotinia sclerotiorum, phytophthora germs, gibberellic disease germs, pyricularia grisea, botrytis cinerea and rhizoctonia solani, can greatly reduce the occurrence of crop diseases, and has a good application prospect. Healthy growth of the crops is powerfully guaranteed, the yield of the crops is practically improved, and a solid and reliable technical support is provided for stability and development of agricultural production.

Description

Technical Field

[0001] The present invention belongs to the technical field of pharmaceutical drugs. Specifically, it relates to a 1-(2-chloromethylphenyl)-3-arylimidazolin-2-one compound, its preparation method and uses. Background Art

[0002] Imidazolinone compounds, as an important class of nitrogen-containing heterocyclic compounds, have attracted much attention in the fields of pharmaceutical and pesticide research and development due to their unique structures and remarkable biological activities. In recent years, with the upgrading of the demand for agricultural disease control and the exacerbation of the problem of drug resistance, the development of new heterocyclic compound pesticides with both high efficiency and safety has become a research hotspot.

[0003] In the field of pesticides, imidazolinone derivatives have been highly regarded due to the specificity of their action mechanisms against pathogenic bacteria. For example, the ferrocenyl-containing imidazolinone compounds synthesized by Xu Zhifeng et al. (2003) showed strong inhibitory activities against Rhizoctonia solani, Physalospora piricola and Gibberella zeae; the imidazolinone derivatives reported by Li Yihao et al. (2021) achieved control effects of 85% and 80% against wheat powdery mildew and cucumber downy mildew respectively at a concentration of 400 mg / L, highlighting the application value of such compounds in agricultural disease prevention and control. In the field of medicine, the imidazolinone compounds synthesized by El-Saghier et al. (2023) showed broad-spectrum antibacterial activities comparable to those of chloramphenicol, providing a new direction for the development of anti-infective drugs. Despite certain progress in existing research, the synthesis of imidazolinone compounds still has significant bottlenecks: on the one hand, most reported synthetic routes involve high-temperature and high-pressure conditions or noble metal catalysts, resulting in high process costs; on the other hand, there are few studies on imidazolinone compounds with both aryl substitution and chloromethyl functionalization. Based on this, we innovatively developed the synthesis of 1-(2-chloromethylphenyl)-3-arylimidazolin-2-one compounds and studied their antibacterial activities to address the existing deficiencies. Summary of the Invention

[0004] The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and provide a 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound, a preparation method and uses thereof. This type of compound uses an aromatic amine compound and bromoacetyl bromide as raw materials, triethylamine as an acid-binding agent, and dichloroethane as a solvent to react in an ice-water bath to obtain a 2-bromoacetyl aromatic amine compound. Then, the 2-bromoacetyl aromatic amine compound and 2-aminobenzyl alcohol are reacted under the action of potassium carbonate in a mixed solvent of N,N-dimethylformamide and tetrahydrofuran to obtain an N-substituted arylacetamide compound. Further, the N-substituted arylacetamide compound is reduced with lithium aluminum hydride in tetrahydrofuran to obtain a 2-(arylaminoethylamino)benzyl alcohol compound. Further, the 2-(arylaminoethylamino)benzyl alcohol compound is reacted with triphosgene in tetrahydrofuran to obtain a 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound with bactericidal activity. The raw materials are cheap and easily available, the synthesis method is simple, and the key intermediate is constructed through a low-temperature controllable reaction of an aromatic amine compound and bromoacetyl bromide. Combining the solvent system optimization and stepwise cyclization strategy, the technical problems of poor functional group compatibility and many by-products in the traditional method are successfully solved.

[0005] To solve the above technical problems, the basic concept of the technical solution adopted by the present invention is:

[0006] On the one hand, the present invention provides a 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound, which is a compound with the structural general formula (Ⅵ),

[0007]

[0008] In formula (Ⅵ), R is one of H and halogen atoms; R 1 is one of C1-C6 alkyl, halogen atom, methoxy group or H.

[0009] Preferably, R is one of H and halogen atoms; R 1 is one of C1-C3 alkyl, H, halogen atom or methoxy group.

[0010] Preferably, R is H; R 1 is one of H, methyl, chlorine atom, methoxy group.

[0011] Preferably, the 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound with the structural general formula (Ⅵ) is specifically selected from one or more of the following compounds:

[0012] 1-(2-chloromethylphenyl)-3-phenyl imidazolin-2-one:

[0013]

[0014] 1-(2-Chloromethylphenyl)-3-(p-tolyl)imidazolin-2-one:

[0015]

[0016] 1-(2-Chloromethylphenyl)-3-(m-tolyl)imidazolin-2-one:

[0017]

[0018] 1-(2-Chloromethylphenyl)-3-(o-tolyl)imidazolin-2-one:

[0019]

[0020] 1-(2-Chloromethylphenyl)-3-(4-chlorophenyl)imidazolin-2-one:

[0021]

[0022] 1-(2-Chloromethylphenyl)-3-(3-chlorophenyl)imidazolin-2-one:

[0023]

[0024] 1-(2-Chloromethylphenyl)-3-(2-chlorophenyl)imidazolin-2-one:

[0025]

[0026] 1-(2-Chloromethylphenyl)-3-(4-methoxyphenyl)imidazolin-2-one:

[0027]

[0028] 1-(2-Chloromethylphenyl)-3-(3-methoxyphenyl)imidazolin-2-one:

[0029]

[0030] On the other hand, the present invention provides a method for preparing 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compounds with the structural general formula (Ⅵ), which specifically includes the following steps:

[0031] S1) Reacting an aromatic amine compound with the structural formula (Ⅰ) and bromoacetyl bromide as raw materials, using triethylamine as an acid-binding agent and dichloroethane as a solvent in an ice-water bath to obtain a 2-bromoacetyl aromatic amine compound with the structural general formula (Ⅱ);

[0032]

[0033] S2) React the 2-bromoacetylarylamine compounds with the general formula (II) and 2-aminobenzyl alcohol under the action of potassium carbonate in a mixed solvent of N,N-dimethylformamide and tetrahydrofuran to obtain N-substituted arylacetamide compounds with the structural general formula (IV);

[0034]

[0035] S3) Reduce the N-substituted arylacetamide compounds with the structural general formula (IV) using lithium aluminum hydride in tetrahydrofuran to obtain 2-(arylaminoethylamino)benzyl alcohol compounds with the structural general formula (V);

[0036]

[0037]

[0038] S4) React the 2-(arylaminoethylamino)benzyl alcohol compounds with the structural general formula (V) and triphosgene in tetrahydrofuran to obtain 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compounds with the structural general formula (VI);

[0039]

[0040] In formula (IV), R is one of H and halogen atoms; R 1 is one of C1-C6 alkyl, halogen atom, methoxy group or H.

[0041] Preferably, R is H; R 1 is one of H, methyl, chlorine atom, methoxy group.

[0042] Preferably, the arylamine compound is one of aniline, p-toluidine, m-toluidine, o-toluidine, 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 4-methoxyaniline, 3-methoxyaniline.

[0043] Preferably, step S1) is specifically: Weigh the arylamine compound with the structural formula (I) and triethylamine, add them to a 250 mL round-bottom flask equipped with a drying tube, measure CH 2 Cl 2 and pour it into the round-bottom flask, then weigh bromoacetyl bromide and pour it into the constant pressure dropping funnel containing CH 2 Cl 2 Under the condition of an ice-water bath, slowly add the diluted bromoacetyl bromide solution to the round-bottom flask. After the addition of bromoacetyl bromide is complete, the mixture is continuously stirred for 30 min to obtain the 2-bromoacetylarylamine compounds with the structural general formula (II);

[0044] In the present invention, in step S1), the preferred reaction molar ratio of the aromatic amine compound having the structural formula (Ⅰ), bromoacetyl bromide and triethylamine is 1:0.92:1.2, the preferred temperature is 0 °C, and the preferred reaction time is 30 min.

[0045] Preferably, step S2) is specifically as follows: Weigh 2-bromoacetyl aromatic amine compounds having the general structural formula (Ⅱ), 2-aminobenzyl alcohol, K 2 CO 3 Add them to a 150 mL round-bottom flask containing a mixed solvent of DMF and THF (V:V = 1:2), stir, and heat to reflux at 65 °C for 1 h. After the reaction is completed, remove the solvent under reduced pressure, add 30 mL of saturated NaCl solution, and then extract with ethyl acetate (30 mL × 3 times). The organic phase is washed successively with water (30 mL × 2 times) and saturated NaCl solution (30 mL × 2 times), wash away the unevaporated DMF with water, and then dry the organic phase with anhydrous Na 2 SO 4 Dry, filter by suction, and concentrate under reduced pressure to obtain a crude product, which is separated and purified by column chromatography to obtain N-substituted arylacetamide compounds having the general structural formula (Ⅳ).

[0046] In the present invention, in step S2), the preferred reaction molar ratio of the 2-bromoacetyl aromatic amine compound having the general structural formula (Ⅱ), 2-aminobenzyl alcohol and potassium carbonate is 1.2:1:1.5, the preferred temperature is 65 °C, and the preferred reaction time is 1 h.

[0047] Preferably, step S3) is specifically as follows: Weigh N-substituted arylacetamide compounds having the general structural formula (Ⅳ) and put them into a three-necked flask. Add THF solvent to the three-necked flask. Weigh LiAlH 4 Introduce nitrogen as a protective gas and add it in batches under an ice-water bath condition. Stir for 30 min and then heat to reflux at 65 °C for 24 h. After the reaction is completed, cool it, slowly add distilled water, then add 15% sodium hydroxide solution and distilled water, stir for 2 - 3 min, filter by suction, wash the filter cake with ethyl acetate, extract the filtrate with ethyl acetate (10 ml × 2 times), wash the organic phase successively with water (15 mL × 2 times) and saturated NaCl solution (15 mL × 2 times), and then dry it with anhydrous Na 2 SO 4 Dry. Filter by suction, and the crude product obtained after removing the solvent under reduced pressure is rapidly separated by column chromatography to obtain 2-(arylaminoethylamino)benzyl alcohol compounds having the general structural formula (Ⅴ).

[0048] Preferably, step S4) is specifically to weigh the 2-(arylaminoethylamino)benzyl alcohol compound of structural formula (V), add triethylamine into a round-bottom flask, and add tetrahydrofuran for dissolution. Dissolve triphosgene in tetrahydrofuran and slowly drip it into the reaction flask through a constant-pressure dropping funnel under stirring in an ice-water bath. After all the dripping is completed, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. The 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound of structural formula (VI) is obtained by column chromatography separation.

[0049] In the chemical reaction system of the present invention, introducing triethylamine has a dual key role. First, it can effectively remove acidic impurities that may exist in the reactant system, such as hydrochloric acid, etc., to purify the reaction environment; second, it can neutralize the hydrobromic acid generated by bromoacetyl bromide and the reactants during the reaction, which will strongly promote the reaction and significantly improve the reaction conversion rate and product yield.

[0050] Preferably, in the reaction stage of S1), the selected solvent is an organic solvent, and dichloromethane (CH 2 Cl 2 ) is the best choice. In this reaction, the molar ratio of the input amount of bromoacetyl bromide to the arylamine compound is controlled in the range of 0.9 - 1.2:1, and a more suitable ratio range is 1 - 1.1:1. At the same time, the addition amount of triethylamine and the molar ratio of the arylamine compound should be controlled in the range of 0.8 - 1.2:1, and the further optimized ratio is 0.9 - 1.1:1.

[0051] Preferably, in the reaction stage of S2), the molar ratio of the 2-bromoacetylarylamine compound of structural formula (II) to 2-aminobenzyl alcohol is set in the range of 1.1 - 1.3:1, and it is experimentally found that a ratio of 1.15 - 1.25:1 can achieve a better reaction effect. In addition, the molar ratio of the 2-bromoacetylarylamine compound of structural formula (II) to K 2 CO 3 is maintained at 1:1.1 - 1.3, and a ratio of 1:1.15 - 1.25 is more conducive to the efficient progress of the reaction.

[0052] Preferably, regarding the selection of the reaction solvent, the present invention has been specifically optimized according to the characteristics and requirements of different reaction steps. In the reaction of S1), for the synthesis of 2-bromoacetanilide compounds, dichloromethane becomes the main solvent due to its good solubility and chemical stability. In the reaction of S2), for the synthesis of N-substituted arylacetamide compounds of (IV), a mixed solvent of N,N-dimethylformamide (DMF) and tetrahydrofuran (THF) with a volume ratio of 1:2 exhibits the best dissolution performance and reaction activity, and thus serves as the main reaction solvent.

[0053] Preferably, in the dropping stage of the reaction of S1), the dropping temperature of the bromoacetyl bromide solution is controlled at 0-5°C, and a low-temperature environment of 0-2°C can better inhibit the occurrence of side reactions and ensure the smooth progress of the reaction. The reaction duration at this stage is controlled at 0.5-1.5 h, and a reaction time of 0.5-1 h can not only ensure the full progress of the reaction but also improve production efficiency.

[0054] Preferably, in the reaction of S2), the reaction temperature for heating under reflux is maintained at 60-70°C. After optimization, a temperature range of 63-67°C can achieve a better balance between the reaction rate and the product yield. The reaction time at this stage is set to 0.5-2 h, and it is found through experiments that a reaction duration of 0.8-1.2 h can effectively ensure the integrity of the reaction and the product quality.

[0055] Preferably, in terms of product separation and purification, the present invention adopts appropriate separation methods for different reaction products. After the reaction of S1), the preferred operation process is as follows: First, wash the reaction product with distilled water, then perform suction filtration, and then recrystallize the crude product with absolute ethanol to obtain a high-purity product. After the reaction of S2) is completed, first perform vacuum desolvation, then add saturated NaCl solution, and then extract with ethyl acetate multiple times. The organic phase after extraction is washed twice with 30 mL of water and twice with 30 mL of saturated NaCl solution to completely remove the remaining unreacted raw materials and by-products.

[0056] Preferably, as a further optimization measure of the present invention, during the treatment of the organic phase after extraction in the reaction of S2), anhydrous Na 2 SO 4 is used for drying treatment to effectively remove the residual moisture in the organic phase and ensure the accuracy of subsequent reactions or analyses.

[0057] Preferably, the molar ratio of the addition amount of lithium aluminum hydride (LiAlH4) to the N-substituted arylacetamide compound of the structural general formula (IV) is 4.2-5:1, preferably 4.4-4.8:1, and more preferably 4.5-4.6:1.

[0058] Preferably, when adding lithium aluminum hydride to the reaction system, it is added in batches under an ice-water bath condition. This is because lithium aluminum hydride reacts violently with water, and the ice-water bath can reduce the reaction rate, avoiding danger caused by overly violent reaction. At the same time, adding in batches can make the reaction proceed more evenly and stably.

[0059] Preferably, after adding lithium aluminum hydride and stirring for 30 min, the reaction system is heated to 60 - 70 °C for reflux, preferably 63 - 67 °C, more preferably 65 °C. Reacting at this temperature for 20 - 28 h, preferably 22 - 26 h, more preferably 24 h, can make the reaction proceed sufficiently and improve the production rate of the product.

[0060] Preferably, in the post-treatment stage after the reaction ends, after the reaction system cools down, distilled water is slowly added. The purpose is to decompose the excessive lithium aluminum hydride and convert it into a water-soluble product for subsequent treatment. Subsequently, 15% sodium hydroxide solution is added, which helps to adjust the pH of the system, precipitate some metal ions, and further separate impurities. Then, an appropriate amount of distilled water is added to better dissolve the inorganic salts and other impurities generated by the reaction for subsequent separation.

[0061] Preferably, the organic phase after extraction is washed successively with water (15 mL each time, 2 times in total) and saturated NaCl solution (15 mL each time, 2 times in total). Washing with water can remove the residual water-soluble impurities in the organic phase, and washing with saturated NaCl solution helps to further remove the residual water and some possible salt impurities, while reducing the dissolution loss of the product in the aqueous phase.

[0062] Preferably, the present invention also includes drying the washed organic phase, using anhydrous Na 2 SO 4 for drying treatment.

[0063] Preferably, the present invention also includes a desolvation process for the dried product, using the method of rotary evaporation under reduced pressure.

[0064] Preferably, the solvent used in the reaction system for preparing 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-ones of structural general formula (Ⅵ) from 2-(arylaminoethylamino)benzyl alcohol compounds of structural general formula (Ⅴ) is tetrahydrofuran, which has good solubility for both the reaction substrate and triphosgene, facilitating the uniform progress of the reaction. In the initial stage, 30 mL of tetrahydrofuran is added to dissolve the compound of structural general formula (Ⅴ) and triethylamine, providing a homogeneous liquid phase environment for the reaction.

[0065] Preferably, the molar ratio of the amount of triethylamine added to the 2-(arylaminoethylamino)benzyl alcohol compound of structural formula (V) is 2.5 - 3.5:1, preferably 2.8 - 3.2:1, and more preferably 3:1. Its main function is to neutralize the acidic substances that may be generated during the reaction and promote the reaction.

[0066] Preferably, the molar ratio of the amount of triphosgene added to the 2-(arylaminoethylamino)benzyl alcohol compound of structural formula (V) is 0.9 - 1.1:1, preferably 0.95 - 1.05:1, and more preferably 1:1. Dissolve triphosgene in tetrahydrofuran and slowly add it dropwise into the reaction flask through a constant pressure dropping funnel under stirring in an ice-water bath. Such an operation method can effectively control the reaction rate, avoid the reaction from being too violent, and at the same time ensure the sufficiency and selectivity of the reaction.

[0067] Preferably, the initial stage of the reaction is carried out under ice-water bath conditions, which helps to reduce the reaction activity when adding triphosgene and prevent side reactions from occurring. After all the triphosgene has been added dropwise, transfer the reaction system to an oil bath at 60 - 70 °C, preferably 63 - 67 °C, and more preferably 65 °C, and continue the reaction for 2.5 - 3.5 h, preferably 2.8 - 3.2 h, and more preferably 3 h to ensure that the reaction is fully completed and improve the product formation rate.

[0068] Preferably, the organic phases after multiple extractions are combined and dried using anhydrous Na 2 SO 4 . Anhydrous Na 2 SO 4 With its strong water absorption, it can efficiently remove the trace moisture remaining in the organic phase and ensure the purity of the subsequent product.

[0069] On the other hand, the present invention provides a use of a 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having structural formula (VI) or a 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having structural formula (VI) prepared by the above method, and uses the 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having structural formula (VI) for antibacterial of crops; specifically for inhibiting one or more of Gibberella zeae, Magnaporthe oryzae, Phytophthora infestans, Sclerotinia sclerotiorum, Botrytis cinerea, and Rhizoctonia solani.

[0070] Preferably, the 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having structural formula (VI) is used to inhibit Phytophthora infestans, Sclerotinia sclerotiorum, Magnaporthe oryzae, and Gibberella zeae.

[0071] On the other hand, the present invention provides a 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having the structural general formula (VI), or the use of a 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having the structural general formula (VI) prepared by the above method. The 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having the structural general formula (VI) is used for preparing a drug for inhibiting bacteria in crops, specifically for preparing a drug for inhibiting one or more of Gibberella zeae, Magnaporthe oryzae, Phytophthora infestans, Sclerotinia sclerotiorum, Botrytis cinerea and Rhizoctonia solani.

[0072] Preferably, the 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound having the structural general formula (VI) is used for preparing a drug for inhibiting Phytophthora infestans, Sclerotinia sclerotiorum, Magnaporthe oryzae and Gibberella zeae.

[0073] The preparation method of the compound of the present invention is simple. Using common and inexpensive arylamine compounds and bromoacetyl bromide as starting materials, triethylamine as an acid-binding agent, and dichloroethane as a solvent, reacting under an ice-water bath condition to generate 2-bromoacetylarylamine compounds. Subsequently, the 2-bromoacetylarylamine compounds and 2-aminobenzyl alcohol are reacted under the action of potassium carbonate in a mixed solvent of N,N-dimethylformamide and tetrahydrofuran to successfully prepare N-substituted arylacetamide compounds. Then, lithium aluminum hydride is used to reduce the N-substituted arylacetamide compounds in tetrahydrofuran to obtain 2-(arylaminoethylamino)benzyl alcohol compounds. Finally, the 2-(arylaminoethylamino)benzyl alcohol compounds and triphosgene are reacted in tetrahydrofuran, and the reaction conditions are precisely controlled to obtain 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compounds.

[0074] Particularly importantly, the 1-(2-chloromethylphenyl)-3-aryl-imidazolin-2-one compound of the present invention has good antibacterial activity against crop bacteria. This compound can exhibit good inhibitory activity against common and severely harmful bacteria such as Gibberella zeae, Phytophthora infestans, Magnaporthe oryzae, Sclerotinia sclerotiorum, Botrytis cinerea and Rhizoctonia solani. By effectively inhibiting the growth and reproduction of these bacteria, the occurrence of crop diseases can be greatly reduced, the healthy growth of crops can be strongly guaranteed, and thus the yield of crops can be effectively improved, providing a solid and reliable technical support for the stability and development of agricultural production.

[0075] After adopting the above technical solutions, the present invention has the following beneficial effects compared with the prior art.

[0076] The present invention innovatively developed a synthetic strategy for 1-(2-chloromethylphenyl)-3-arylimidazolin-2-ones. By carrying out a low-temperature controllable reaction between arylamine compounds and bromoacetyl bromide to construct key intermediates, combined with the optimization of the solvent system and the stepwise cyclization strategy, the technical problems such as poor functional group compatibility and many by-products in traditional methods were successfully solved. The obtained compounds not only exhibit good bactericidal activity, but also the chloromethyl functional module provides an important platform for subsequent structural modification and activity optimization, showing significant application value in addressing crop disease control and drug resistance challenges.

[0077] 1. The preparation of the 1-(2-chloromethylphenyl)-3-arylimidazolin-2-ones with the structural general formula (Ⅵ) in the present invention is a brand-new compound, and this compound has good antibacterial activity against crops; in particular, it has good inhibitory activity against Gibberella zeae, Magnaporthe oryzae, Phytophthora infestans, Sclerotinia sclerotiorum, Botrytis cinerea, and Rhizoctonia solani.

[0078] 2. In the preparation method of the 1-(2-chloromethylphenyl)-3-arylimidazolin-2-ones with the structural general formula (Ⅵ) provided by the present invention, the synthetic raw materials are cheap and easily available, the synthetic method is simple, the yield is relatively high, and the product is easy to separate and purify.

[0079] The following further describes in detail the specific embodiments of the present invention with reference to the accompanying drawings. Description of the Drawings

[0080] As a part of this application, the accompanying drawings are used to provide a further understanding of the present invention. The schematic embodiments of the present invention and their descriptions are used to explain the present invention, but do not constitute an improper limitation of the present invention. Obviously, the following-described drawings are only some embodiments. For those of ordinary skill in the art, other drawings can also be obtained based on these drawings without creative efforts. In the drawings:

[0081] Figure 1 is the structural diagram of the 1-(2-chloromethylphenyl)-3-arylimidazolin-2-ones with the structural general formula (Ⅵ) described in the present invention.

[0082] Figure 2 is the synthetic route diagram of the 1-(2-chloromethylphenyl)-3-arylimidazolin-2-ones with the structural general formula (Ⅵ) of the present invention.

[0083] It should be noted that these drawings and text descriptions are not intended to limit the scope of the concept of the present invention in any way, but to illustrate the concept of the present invention to those skilled in the art by referring to specific embodiments. Specific Embodiments

[0084] To make the objectives, technical solutions, and advantages of the embodiments of the present invention clearer, the following will, in conjunction with the accompanying drawings in the embodiments of the present invention, clearly and completely describe the technical solutions in the embodiments. The following embodiments are used to illustrate the present invention but are not used to limit the scope of the present invention.

[0085] The structural formula of the intermediate product of the present invention is shown in Table 1 below

[0086] Table 1 Structural formula of the intermediate product

[0087]

[0088]

[0089]

[0090] The sources of the chemical reagents used in the embodiments of the present invention are as follows:

[0091] Wuhan Great Wall Reagent Co., Ltd.: Bromoacetyl bromide (CAS: 598-21-0), 2-Chloroaniline (CAS: 95-51-2), 3-Chloroaniline (CAS: 108-42-9), 4-Chloroaniline (CAS: 106-47-8).

[0092] Shandong Xiya Chemical Industry Co., Ltd.: 2-Methylaniline (CAS: 95-53-4), 3-Methylaniline (CAS: 108-44-1).

[0093] Shanghai Macklin Biochemical Co., Ltd.: 4-Methylaniline (CAS: 106-49-0), Benzylamine (CAS: 100-46-9).

[0094] Tianjin Damao Reagent Co., Ltd.: Aniline (CAS: 62-53-3).

[0095] Jiuding Chemistry (Shanghai) Co., Ltd.: 3-Methoxyaniline (CAS: 536-90-3), 4-Methoxyaniline (CAS: 104-94-9).

[0096] Saan Chemical Technology (Shanghai) Co., Ltd.: 3-Methoxybenzylamine (CAS: 5071-96-5), 4-Methoxybenzylamine (CAS: 2393-23-9).

[0097] Alfa Aesar (Tianjin) Co., Ltd.: 2-Methoxybenzylamine (CAS: 6850-57-3).

[0098] Shanghai Anage Technology Co., Ltd.: 2-Methylbenzylamine (CAS: 89-93-0), 3-ethylaniline (CAS: 587-02-0), 2-aminobenzyl alcohol (CAS: 5344-90-1), lithium aluminum hydride (CAS: 16853-85-3).

[0099] Beijing Bailingwei Technology Co., Ltd.: 4-Methylbenzylamine (CAS: 104-84-7).

[0100] Shanghai Myrel Chemical Technology Co., Ltd.: benzylamine (CAS: 100-46-9), triethylamine (CAS: 121-44-8), potassium carbonate (CAS: 584-08-7), triphosgene (CAS: 32315-10-9), anhydrous sodium sulfate (CAS: 7757-82-6).

[0101] Xilong Scientific Co., Ltd.: Tetrahydrofuran (CAS: 109-99-9), N,N-dimethylformamide (CAS: 68-12-2).

[0102] Hunan Huihong Reagent Co., Ltd.: Dichloromethane (CAS: 75-09-2).

[0103] Example A1

[0104] Synthesis of 1-(2-chloromethylphenyl)-3-phenylimidazolin-2-one:

[0105]

[0106] Weigh the prepared 2-(2-(phenylamino)ethylamino)benzyl alcohol (0.287 g, 1 mmol), triethylamine (0.304 g, 3 mmol) and add them to a 100 mL round-bottom flask, and add 30 mL of tetrahydrofuran to dissolve. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly drip into the reaction bottle through a constant pressure dropping funnel under stirring in an ice-water bath. After all the dripping is completed, transfer to a 65°C oil bath and continue to react for 3 hours. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and use anhydrous Na 2 SO4, and the solvent was removed by rotary evaporation under reduced pressure. A white solid was obtained by column chromatography with a yield of 92.1%.

[0107] 1 HNMR (400MHz, CDCl 3) δ 7.51 (dd, J = 8.7, 0.9 Hz, 2H), 7.42 (dd, J = 7.6, 1.4 Hz, 1H), 7.34 - 7.30 (m, 1H), 7.30 - 7.25 (m, 2H), 7.25 - 7.13 (m, 2H), 7.00 (t, J = 7.4 Hz, 1H), 4.62 (s, 2H), 3.96 - 3.90 (m, 2H), 3.90 - 3.85 (m, 2H).

[0108] 13 C NMR (101 MHz, CDCl 3 ) δ 156.38, 140.24, 138.16, 136.05, 131.01, 129.82 (2C), 129.00, 127.97, 126.55, 122.97, 117.75 (2C), 45.25, 43.43, 43.07.

[0109] Example A2

[0110] Synthesis of 1-(2-chloromethylphenyl)-3-(p-tolyl)imidazolin-2-one:

[0111]

[0112] Weigh the prepared 2-(2-(4-methylphenylamino)ethylamino)benzyl alcohol (0.301 g, 1 mmol) and triethylamine (0.304 g, 3 mmol), add them to a 100 mL round-bottom flask, and dissolve them in 30 mL of tetrahydrofuran. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise to the reaction flask through a constant pressure dropping funnel under stirring in an ice-water bath. After complete addition, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases, dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. A white solid was obtained by column chromatography separation with a yield of 94.8%.

[0113] 1 HNMR (400 MHz, CDCl 3 ) δ 7.42 (dd, J = 7.6, 1.4 Hz, 1H), 7.40 (s, 1H), 7.38 (s, 1H), 7.30 (td, J = 7.6, 1.6 Hz, 1H), 7.25 - 7.19 (m, 2H), 7.08 (d, J = 8.4 Hz, 2H), 4.62 (s, 2H), 3.93 - 3.88 (m, 2H), 3.88 - 3.84 (m, 2H), 2.24 (s, 3H).

[0114] 13 C NMR (101 MHz, CDCl 3 ) δ 156.49, 138.28, 137.75, 136.04, 132.54, 130.99, 129.77, 129.51 (2C), 127.86, 126.47, 117.90 (2C), 45.30, 43.45, 43.21, 20.81.

[0115] Example A3

[0116] Synthesis of 1-(2-chloromethylphenyl)-3-(m-tolyl)imidazolin-2-one:

[0117]

[0118] Weigh the prepared 2-(2-(3-methylphenylamino)ethylamino)benzyl alcohol (0.301 g, 1 mmol), add triethylamine (0.304 g, 3 mmol) to a 100 mL round-bottom flask, and add 30 mL of tetrahydrofuran to dissolve. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly drip it into the reaction flask through a constant pressure dropping funnel under stirring in an ice-water bath. After all the dripping is completed, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases, dry with anhydrous Na 2 SO 4 dry, and remove the solvent by rotary evaporation under reduced pressure. A white solid was obtained by column chromatography separation, and the yield was 90.1%.

[0119] 1 HNMR (400 MHz, CDCl 3 ) δ 7.41 - 7.35 (m, 2H), 7.25 (ddd, J = 5.2, 3.1, 1.1 Hz, 2H), 7.22 - 7.11 (m, 3H), 6.80 (d, J = 7.5 Hz, 1H), 4.59 (s, 2H), 3.87 - 3.82 (m, 2H), 3.82 - 3.76 (m, 2H), 2.25 (s, 3H).

[0120] 13 C NMR (101 MHz, CDCl 3)δ 156.41, 140.19, 138.77, 138.19, 135.99, 130.93, 129.76, 128.79, 127.87, 126.45, 123.82, 118.59, 114.83, 45.19, 43.43, 43.13, 21.81.

[0121] Example A4

[0122] Synthesis of 1-(2-chloromethylphenyl)-3-(o-tolyl)imidazolin-2-one:

[0123]

[0124] Weigh the prepared 2-(2-(2-methylphenylamino)ethylamino)benzyl alcohol (0.301 g, 1 mmol) and triethylamine (0.304 g, 3 mmol), add them to a 100 mL round-bottom flask, and add 30 mL of tetrahydrofuran to dissolve. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise into the reaction flask through a constant pressure dropping funnel under stirring in an ice-water bath. After all the addition is completed, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. Obtain a yellow oil by column chromatography separation, and the yield is 77.7%.

[0125] 1 HNMR (400 MHz, DMSO-d 6 ) δ 7.68 - 7.64 (m, 1H), 7.41 - 7.38 (m, 3H), 7.38 - 7.34 (m, 2H), 7.33 - 7.27 (m, 2H), 4.67 (s, 2H), 3.93 (td, J = 6.8, 2.2 Hz, 4H), 2.37 (s, 3H).

[0126] 13 C NMR (101 MHz, CDCl 3 ) δ 157.39, 140.52, 139.09, 137.48, 136.31, 131.31, 128.28, 127.82, 127.38, 127.12, 127.07, 126.98, 126.02, 59.83, 46.09, 45.84, 18.29.

[0127] Example A5

[0128] Synthesis of 1-(2-chloromethylphenyl)-3-(4-chlorophenyl)imidazolin-2-one:

[0129]

[0130] Weigh the prepared 2-(2-(4-chloroanilino)ethylamino)benzyl alcohol (0.321 g, 1 mmol) and triethylamine (0.304 g, 3 mmol), add them to a 100 mL round-bottom flask, and dissolve them in 30 mL of tetrahydrofuran. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise to the reaction flask through a constant-pressure dropping funnel under stirring in an ice-water bath. After all the addition is completed, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. A white solid is obtained by column chromatography separation, and the yield is 93.2%.

[0131] 1 HNMR(400MHz,CDCl 3 )δ7.47-7.43(m,2H),7.41(dd,J=7.6,1.5Hz,1H),7.30(dd,J=7.6,1.6Hz,1H),7.24(dt,J=5.1,1.7Hz,2H),7.19(dt,J=7.8,1.6Hz,2H),4.60(s,2H),3.87(s,4H).

[0132] 13 C NMR(101MHz,CDCl 3 )δ156.12,138.84,137.89,135.99,131.01,129.85,128.88,128.09(2C),127.88,126.66,118.80(2C),45.13,43.33,42.96.

[0133] Example A6

[0134] Synthesis of 1-(2-chloromethylphenyl)-3-(3-chlorophenyl)imidazolin-2-one:

[0135]

[0136] Weigh the prepared 2-(2-(3-chlorophenylamino)ethylamino)benzyl alcohol (0.321 g, 1 mmol), add triethylamine (0.304 g, 3 mmol) to a 100 mL round-bottom flask, and add 30 mL of tetrahydrofuran to dissolve. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise to the reaction flask through a constant pressure dropping funnel under stirring in an ice-water bath. After all the addition is completed, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry and remove the solvent under reduced pressure. A white solid is obtained by column chromatography separation, and the yield is 89.7%.

[0137] 1 HNMR (400 MHz, CDCl 3 ) δ 7.65 (t, J = 2.1 Hz, 1H), 7.48 (ddd, J = 8.4, 4.9, 1.5 Hz, 2H), 7.39 (td, J = 7.6, 1.7 Hz, 1H), 7.33 (td, J = 7.5, 1.4 Hz, 1H), 7.29 - 7.24 (m, 2H), 7.06 - 7.00 (m, 1H), 4.68 (s, 2H), 3.99 - 3.93 (m, 4H).

[0138] 13 CNMR (101 MHz, CDCl 3 ) δ 156.01, 141.39, 137.81, 136.02, 134.69, 131.04, 129.90, 129.96, 128.18, 126.71, 122.78, 117.62, 115.48, 45.12, 43.37, 42.92.

[0139] Example A7

[0140] Synthesis of 1-(2-chloromethylphenyl)-3-(2-chlorophenyl)imidazolin-2-one:

[0141]

[0142] Weigh the prepared 2-(2-(2-chlorophenylamino)ethylamino)benzyl alcohol (0.321 g, 1 mmol), and add triethylamine (0.304 g, 3 mmol) into a 100 mL round-bottom flask. Then add 30 mL of tetrahydrofuran to dissolve them. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly drip it into the reaction flask through a constant-pressure dropping funnel under stirring in an ice-water bath. After complete dripping, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. Yellow oil is obtained by column chromatography separation, and the yield is 75.5%.

[0143] 1 HNMR (400 MHz, DMSO-d 6 ) δ 7.59 - 7.55 (m, 2H), 7.51 (dd, J = 7.7, 1.3 Hz, 1H), 7.41 (d, J = 7.7 Hz, 1H), 7.36 (dd, J = 7.7, 1.4 Hz, 1H), 7.34 - 7.30 (m, 3H), 4.57 (s, 2H), 3.95 - 3.87 (m, 4H).

[0144] 13 C NMR (101 MHz, CDCl 3 ) δ 157.23, 140.56, 137.74, 137.01, 132.27, 130.62, 130.27, 129.23, 128.54, 128.17, 127.78, 127.27, 126.05, 59.67, 46.03, 45.54.

[0145] Example A8

[0146] Synthesis of 1-(2-chloromethylphenyl)-3-(4-methoxyphenyl)imidazolin-2-one:

[0147]

[0148] Weigh the prepared 2-(2-(4-methoxyphenylamino)ethylamino)benzyl alcohol (0.317 g, 1 mmol), add triethylamine (0.304 g, 3 mmol) to a 100 mL round-bottom flask, and dissolve it in 30 mL of tetrahydrofuran. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise to the reaction flask through a constant-pressure dropping funnel under stirring in an ice-water bath. After complete addition, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. A white solid was obtained by column chromatography separation, and the yield was 95.7%.

[0149] 1 HNMR (400 MHz, CDCl 3 ) δ 7.43 7.38 (m, 3H), 7.30 (dd, J = 10.8, 4.4 Hz, 1H), 7.21 (dd, J = 14.7, 7.6 Hz, 2H), 6.85 - 6.80 (m, 2H), 4.62 (s, 2H), 3.89 - 3.81 (m, 4H), 3.69 (d, J = 1.2 Hz, 3H).

[0150] 13 C NMR (101 MHz, CDCl 3 ) δ 156.58, 155.59, 138.26, 135.91, 133.52, 130.90, 129.68, 127.74, 126.36, 119.64 (2C), 114.19 (2C), 55.53, 45.26, 43.46, 43.39.

[0151] Example A9

[0152] Synthesis of 1-(2-chloromethylphenyl)-3-(3-methoxyphenyl)imidazolin-2-one:

[0153]

[0154] Weigh the prepared 2-(2-(3-methoxyphenylamino)ethylamino)benzyl alcohol (0.317 g, 1 mmol), add triethylamine (0.304 g, 3 mmol) to a 100 mL round-bottom flask, and dissolve in 30 mL of tetrahydrofuran. Dissolve triphosgene (0.297, 1 mmol) in tetrahydrofuran and slowly add it dropwise to the reaction flask through a constant-pressure dropping funnel under stirring in an ice-water bath. After complete addition, transfer it to an oil bath at 65 °C and continue the reaction for 3 h. After the reaction is completed, extract with water (30 mL × 2 times), and extract the aqueous phase with DCM (30 mL × 3 times). Combine the organic phases and dry with anhydrous Na 2 SO 4 Dry, and remove the solvent by rotary evaporation under reduced pressure. A white solid is obtained by column chromatography separation, with a yield of 88.7%.

[0155] 1 HNM R(400MHz,CDCl 3 )δ7.42(dd,J=7.6,1.3Hz,1H),7.357.29(m,2H),7.22(ddd,J=20.5,9.3,1.9Hz,3H),6.96-6.92(m,1H),6.56(dd,J=8.3,2.4Hz,1H),4.61(s,2H),3.90(dq,J=7.4,5.6Hz,4H),3.72(s,3H).

[0156] 13 C NMR(101MHz,CDCl 3 )δ160.17,156.34,141.49,138.04,136.07,130.97,129.82,129.59,128.00,126.58,109.50,108.91,103.62,55.30,45.13,43.34,43.14.

[0157] Antibacterial activity test:

[0158] Using the in vitro method, antibacterial activity tests were carried out on 1-(2-chloromethylphenyl)-3-phenylimidazolin-2-one, 1-(2-chloromethylphenyl)-3-(p-tolyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(m-tolyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(o-tolyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(4-chlorophenyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(3-chlorophenyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(2-chlorophenyl)imidazolin-2-one, 1-(2-chloromethylphenyl)-3-(4-methoxyphenyl)imidazolin-2-one, and 1-(2-chloromethylphenyl)-3-(3-methoxyphenyl)imidazolin-2-one.

[0159] Taking Gibberella zeae, Phytophthora capsici, Magnaporthe oryzae, Sclerotinia sclerotiorum, Botrytis cinerea, and Rhizoctonia solani as the test materials for bactericidal activity testing, the test agents were dissolved in acetone and then diluted with 200 g / ml sorpol-144 emulsifier to a 500 g / mL liquid medicine. Under sterile operating conditions, 1 mL of the compound solution was pipetted into a sterilized petri dish, and then 9 mL of sterilized PDA culture medium was pipetted into the petri dish and mixed well to prepare a drug-containing plate with the corresponding concentration. The cultured pathogenic bacteria were cut into disks with a diameter of 4 mm from the edge of the colony under sterile conditions using a sterilized borer. After the culture medium solidified, the disks were inoculated in the center of the drug-containing plate using an inoculator and placed in an incubator at an appropriate temperature for cultivation. A blank control was set without adding the drug. Each treatment was cultured in an incubator at 24 ± 1 °C. After 72 hours, the colony diameter was observed and measured. The diameter of each colony was measured vertically once using the cross method, and the average value was taken.

[0160] Growth inhibition rate (%) = (control colony diameter - treatment colony diameter) × 100 / (control colony diameter - 4 mm).

[0161] The drug concentration was 50 μg / mL. The results of the antibacterial activity test are shown in Table 2.

[0162] Table 2 Antibacterial activity results

[0163]

[0164] As can be seen from Table 2, the target compounds all have antibacterial activity against the test pathogens, and some have good antibacterial activity. Among them, the inhibition rate of 1-(2-chloromethylphenyl)-3-(p-tolyl)imidazolin-2-one against Phytophthora capsici is as high as 80.0%, and the inhibition rate against Magnaporthe oryzae reaches 74.7%; the inhibition rate of 1-(2-chloromethylphenyl)-3-(o-tolyl)imidazolin-2-one against Sclerotinia sclerotiorum reaches 74.7%.

[0165] The above are only the preferred embodiments of the present invention, and do not impose any form of limitation on the present invention. Although the present invention has been disclosed above with the preferred embodiments, it is not intended to limit the present invention. Any person skilled in the art of this patent, without departing from the scope of the technical solution of the present invention, may make some changes or modifications using the technical content prompted above into equivalent embodiments of equivalent changes. However, as long as it does not depart from the content of the technical solution of the present invention, any simple modification, equivalent change and modification made to the above embodiments according to the technical essence of the present invention still fall within the scope of the present invention's solution.

Claims

1. A 1-(2-chloromethylphenyl)-3-aryl imidazoline-2-one compound, characterized in that: The compound has a general structural formula (VI), In formula (VI), R is H or a halogen atom; R 1 It is one of a C1-C6 alkyl group, a halogen atom, a methoxy group or H.

2. The compound according to claim 1, characterized in that R 1 is one of a C1-C3 alkyl group, H, a halogen atom or a methoxy group; Preferably, R is H; R 1 It is one of H, methyl, chlorine atom or methoxy group.

3. A 1-(2-chloromethylphenyl)-3-aryl imidazoline-2-one compound, characterized in that: The compound is selected from one or more of the following compounds: 1-(2-Chloromethylphenyl)-3-phenylimidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(p-tolyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(m-tolyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(o-tolyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(4-chlorophenyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(3-chlorophenyl)imidazolin-2-one: 1-(2-chloromethylphenyl)-3-(2-chlorophenyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(4-methoxyphenyl)imidazolin-2-one: 1-(2-Chloromethylphenyl)-3-(3-methoxyphenyl)imidazolin-2-one:

4. A method for preparing a 1-(2-chloromethylphenyl)-3-aryl imidazoline-2-one compound having a general structural formula (VI), characterized in that: The general structural formula (VI) is: The preparation method specifically comprises the following steps: S1) reacting an aromatic amine compound having structural formula (I) with bromoacetyl bromide as raw materials, triethylamine as an acid-binding agent, and dichloroethane as a solvent in an ice-water bath to obtain a 2-bromoacetyl aromatic amine compound having structural formula (II); S2) reacting a 2-bromoacetyl arylamide compound of the general formula (II) with 2-aminobenzyl alcohol in the presence of potassium carbonate in a mixed solvent of N,N-dimethylformamide and tetrahydrofuran to obtain an N-substituted aryl acetylamide compound of the general formula (IV); S3) reducing the N-substituted aryl acetamide compound having the general structural formula (IV) using lithium aluminum hydride in tetrahydrofuran to obtain a 2-(arylaminoethylamino)benzyl alcohol compound having the general structural formula (V); S4) reacting a 2-(arylaminoethylamino)benzyl alcohol compound having the general structural formula (V) with triphosgene in tetrahydrofuran to obtain a 1-(2-chloromethylphenyl)-3-aryl imidazoline-2-one compound having the general structural formula (VI); In formula (VI), R is H or a halogen atom; R 1 It is one of a C1-C6 alkyl group, a halogen atom, a methoxy group or H.

5. The preparation method according to claim 4, characterized in that: R is H; R 1 is one of H, methyl, chlorine atom and methoxy group; the aromatic amine compound is one of aniline, p-methylaniline, m-methylaniline, o-methylaniline, 4-chloroaniline, 3-chloroaniline, 2-chloroaniline, 4-methoxyaniline and 3-methoxyaniline.

6. The preparation method according to claim 4, characterized in that: Step S1) is specifically as follows: weighing an aromatic amine compound of structural formula (I) and triethylamine, adding them into a 250 mL round-bottom flask with a drying tube, measuring CH2Cl2 and pouring it into the round-bottom flask, then weighing bromoacetyl bromide and pouring it into a constant pressure dropping funnel filled with CH2Cl2, slowly dropping the diluted bromoacetyl bromide solution into the round-bottom flask under ice-water bath conditions, and after the bromoacetyl bromide is added, the mixed solution is continuously stirred for 30 min to obtain a 2-bromoacetyl aromatic amine compound having the general structural formula (II); Step S2) is specifically as follows: weighing a 2-bromoacetyl arylamide compound of the general formula (II), 2-aminobenzyl alcohol, and K2CO3, adding them into a 150 mL round-bottom flask filled with a mixed solvent of DMF and THF, stirring, heating to 65° C. and reflux for 1 h, and tracking and detecting with a TLC plate. After the reaction is completed, desolventizing under reduced pressure, adding 50 mL of a saturated NaCl solution, and then extracting with ethyl acetate three times, washing the organic phase with water twice and a saturated NaCl solution twice in sequence, washing the DMF and THF that were not dried with water, and then drying the organic phase with anhydrous Na2SO4, filtering, and concentrating under reduced pressure to obtain a crude product, and separating and purifying by column chromatography to obtain an N-substituted aryl acetylamide compound having the general formula (IV); Step S3) is specifically as follows: weighing an N-substituted aryl acetamide compound having a general structural formula (IV) and charging it into a three-necked flask, adding THF solvent into the three-necked flask, weighing lithium aluminum hydride and introducing nitrogen as a protective gas, adding in batches under ice-water bath conditions, stirring for 30 minutes, and then heating to 65° C. and reflux for 24 hours. After the reaction is complete, cooling, slowly adding distilled water, then adding 15% sodium hydroxide solution and distilled water, stirring for 2 to 3 minutes, filtering with suction, washing the filter cake with ethyl acetate, extracting the filtrate with ethyl acetate twice, washing the organic phase with water twice and a saturated solution of NaCl twice in sequence, and then drying with anhydrous Na2SO4, filtering with suction, desolventizing and obtaining a crude product, and quickly separating by column chromatography to obtain a 2-(arylaminoethylamino)benzyl alcohol compound having a general structural formula (V); Step S4) is specifically as follows: weigh a 2-(arylaminoethylamino)benzyl alcohol compound of the general formula (V), add triethylamine to a round-bottom flask, and add tetrahydrofuran to dissolve it, dissolve triphosgene in tetrahydrofuran and slowly drip it into the reaction bottle through a constant pressure dropping funnel under stirring in an ice-water bath, and after all the dripping is completed, transfer it to a 65°C oil bath pot and continue to react for 3 hours. After the reaction is completed, extract it with water twice, extract the aqueous phase with DCM three times, combine the organic phases, dry it with anhydrous Na2SO4, remove the solvent by vacuum rotary evaporation, and separate it by column chromatography to obtain a 1-(2-chloromethylphenyl)-3-aryl imidazoline-2-one compound having the general formula (VI).

7. The preparation method according to claim 6, characterized in that: In step S1), the molar ratio of the aromatic amine compound having the structural formula (I), bromoacetyl bromide and triethylamine added is 1:0.9-1.2:0.8-1.2; In step S2), the molar ratio of the 2-bromoacetyl arylamide compound having the general structural formula (II), 2-aminobenzyl alcohol and potassium carbonate added is 1.1-1.3:1:1.21-1.69; In step S3), the molar ratio of the N-substituted aryl acetamide compound having the general structural formula (IV) to lithium aluminum hydride is 1:4.2-5; In step S4), the molar ratio of the added amounts of 2-(arylaminoethylamino)benzyl alcohol compound having the general structural formula (V), triethylamine and triphosgene is 1:2.5-3.5:0.9-1.

1.

8. The preparation method according to claim 6, characterized in that: In step S1), the molar ratio of the aromatic amine compound having the structural formula (I), bromoacetyl bromide and triethylamine added is 1:0.92:1.2; In step S2), the molar ratio of the 2-bromoacetyl arylamide compound having the general structural formula (II), 2-aminobenzyl alcohol and potassium carbonate added is 1.2:1:1.5; In step S3), the molar ratio of the N-substituted aryl acetamide compound having the general structural formula (IV) to lithium aluminum hydride is 1:4.5; In step S4), the molar ratio of the added amounts of 2-(arylaminoethylamino)benzyl alcohol compound having the general structural formula (V), triethylamine and triphosgene is 1:3:

1.

9. Use of a 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound having the general structural formula (VI) according to any one of claims 1 to 3 or a 1-(2-chloromethylphenyl)-3-aryl imidazolin-2-one compound having the general structural formula (VI) prepared by the method according to any one of claims 4 to 8, characterized in that: Used for antibacterial effect on crops, or for preparing antibacterial effect drugs on crops.

10. The use according to claim 9, characterized in that Used for inhibiting fungi in crops, including one or more of sclerotinia, phytophthora, fusarium, rice blast, gray mold, and sheath blight; The drug used for preparing antibacterial drugs for crops includes drugs used for preparing drugs for inhibiting one or more pathogens of Sclerotinia sclerotiorum, Phytophthora, Gibberella, Rice blast, Botrytis cinerea, and Sheath blight.

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