A benzimidazole compound and application thereof

Abstract

The application discloses a kind of benzimidazole compounds and its application, belong to crop growth regulation technical field.The benzimidazole compound structural formula is;Wherein, R1 It is phenothiazine group, NH2 Or halogen;R2 It is H, CH3 Or F;R3 It is phenothiazine group, CH3, NH2, NO2 Or halogen.Benzimidazole compound is 5-nitro-2-(N-phenothiazine group)-1H-benzimidazole, 5-(N-phenothiazine group)-1H-benzimidazole or 2-bromo-5-amino-1H-benzimidazole.The application is modified to different sites of benzimidazole, designs new benzimidazole compound.The raw material of this preparation method is easy to obtain, low in cost, and operation is relatively simple.This benzimidazole compound can promote crop growth and inhibit the activity of pathogenic bacteria, and has good development prospect.

Description

Technical Field

[0001] This invention relates to the field of crop growth regulation technology, specifically to a benzimidazole compound and its applications. Background Technology

[0002] Pathogenic fungi infect plants, causing a series of morphological, physiological, and biochemical pathological changes that hinder normal plant growth and development. Diseases caused by pathogenic fungi constitute the largest category of infectious plant diseases, accounting for approximately 70%–80% of all plant diseases, severely impacting economic benefits. Chemical pesticides play a crucial role in plant disease control; however, the resistance problems resulting from the long-term use of traditional chemical pesticides hinder effective control. Therefore, developing highly effective pesticide components with novel mechanisms of action and low risk of resistance is a vital means to address this issue.

[0003] Benzimidazole compounds are widely used in agriculture, forestry, and horticulture to control various fungal diseases, such as powdery mildew, rust, and downy mildew. Benzimidazole compounds destroy the cell membranes of pathogens, inhibit cell division, and disrupt DNA synthesis, thereby killing the pathogens. Currently, benzimidazole compounds are mainly used as fungicides and antiviral pesticides. Experiments have shown that benzimidazole inhibits crop growth, and there are no reports of its use in regulating crop growth. If benzimidazole compounds could be used simultaneously for antifungal, antiviral, and crop growth promotion, there would be no need to spray multiple pesticides on crops, saving both pesticide usage and labor costs—a win-win situation. Regulating crop growth and increasing crop yield to meet the ever-growing global food demand is key to improving photosynthesis, as the accumulation of plant biomass mainly depends on photosynthesis. Photosynthesis is the process by which plants utilize sunlight and CO2 and convert them into biochemical energy. Improving the utilization rate of sunlight and the absorption of CO2 promotes crop growth, thereby increasing plant yield. If a benzimidazole compound that facilitates CO2 absorption is designed, spraying it can enhance crop growth by increasing CO2 absorption and thus improving photosynthesis. Therefore, a novel benzimidazole compound is needed that possesses both broad-spectrum and highly effective fungicidal activity and the ability to regulate crop growth, thereby improving the development prospects of benzimidazole compounds. Summary of the Invention

[0004] To address the aforementioned limitations of existing technologies, the present invention aims to provide a benzimidazole compound and its applications. This invention designs novel benzimidazole compounds by modifying different sites on benzimidazole. The preparation method utilizes readily available raw materials, is low-cost, and relatively simple to operate. This benzimidazole compound can both promote crop growth and inhibit pathogen activity, demonstrating promising development prospects.

[0005] To achieve the above objectives, the present invention adopts the following technical solution:

[0006] In a first aspect, the present invention provides a benzimidazole compound having the structural formula shown in Formula I:

[0007] Formula I;

[0008] Wherein, R1 is phenothiazine, NH2 or halogen; R2 is H, CH3 or F; R3 is phenothiazine, CH3, NH2, NO2 or halogen.

[0009] Preferably, the benzimidazole compound is 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole, 5-(N-phenthiazinyl)-1H-benzimidazole, or 2-bromo-5-amino-1H-benzimidazole.

[0010] Preferably, the 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole is prepared by the following method:

[0011] (1) 4-nitro-o-phenylenediamine and formic acid were added to hydrochloric acid solution and heated under reflux. After the reaction was completed, the mixture was cooled to room temperature and the pH was adjusted to neutral to obtain a yellow precipitate. After drying, 5-nitrobenzimidazole was obtained.

[0012] (2) Dissolve 5-nitrobenzimidazole and N-bromosuccinimide in organic solvents to obtain 5-nitrobenzimidazole solution and N-bromosuccinimide solution respectively. Mix 5-nitrobenzimidazole solution and N-bromosuccinimide solution to obtain 2-bromo-5-nitro-1H-benzimidazole.

[0013] (3) Add 2-bromo-5-nitro-1H-benzimidazole, phenothiazine, acetonitrile, anhydrous potassium carbonate and potassium iodide to DMF, heat and stir to obtain 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole.

[0014] Preferably, in step (1), the ratio of the amount of 4-nitro-o-phenylenediamine, formic acid and hydrochloric acid solution added is 1.53g:2.5mL:40mL; the concentration of the hydrochloric acid solution is 5mol / L; the temperature of the heating and reflux reaction is 60~80℃, and the heating and reflux reaction time is 1~3h.

[0015] Preferably, in step (2), the organic solvent is DMF or methanol; the concentration of the 5-nitrobenzimidazole solution is 0.067 g / mL; the concentration of the N-bromosuccinimide solution is 0.1 g / mL; the volume ratio of the 5-nitrobenzimidazole solution to the N-bromosuccinimide solution is 3:2; and the mixing temperature is room temperature or 60°C.

[0016] Preferably, in step (3), the mass ratio of 2-bromo-5-nitro-1H-benzimidazole, phenothiazine, acetonitrile, anhydrous potassium carbonate and potassium iodide is 2:1:2:2:0.1; the ratio of the amount of 2-bromo-5-nitro-1H-benzimidazole added to DMF is 2g:50mL; the temperature of the heating reaction is 70℃ and the heating reaction time is 2h.

[0017] Preferably, the 5-(N-phenthiazinyl)-1H-benzimidazole is prepared by the following method:

[0018] 5-Bromo-1H-benzimidazole, phenothiazine, acetonitrile, anhydrous potassium carbonate and potassium iodide were added to a DMF solution, and the mixture was heated and stirred to obtain 5-(N-phenothiazinyl)-1H-benzimidazole.

[0019] Preferably, the preparation method of the 2-bromo-5-amino-1H-benzimidazole is as follows:

[0020] 2-Bromo-5-nitro-1H-benzimidazole and iron powder were added to concentrated hydrochloric acid and reacted in a cold water bath. When the reaction stopped boiling, the mixture was heated in a water bath and stirred to obtain 2-bromo-5-amino-1H-benzimidazole.

[0021] A second aspect of the invention provides the use of benzimidazole compounds in simultaneously promoting plant growth and resisting viruses.

[0022] Preferably, the promotion of plant growth includes: promoting seed germination, promoting seedling growth, and improving seed salt and alkali tolerance.

[0023] The beneficial effects of this invention are:

[0024] (1) This invention modifies different sites of benzimidazole to design and synthesize a series of benzimidazole compounds. This invention provides a novel method for preparing benzimidazole compounds, which involves cyclic reactions, substitution reactions, reduction reactions, etc. The solvents selected are methanol, dimethyl sulfoxide, and acetonitrile. The reaction temperature is relatively low. The raw materials for this preparation method are readily available, the cost is low, and the operation is relatively simple.

[0025] (2) The benzimidazole compounds of the present invention can promote plant growth, such as promoting seed germination, root and stem elongation, and fresh biomass, and also have a positive effect on improving plant resistance, such as salt and alkali tolerance. On the other hand, they can effectively inhibit pathogen activity. Pharmacological experiments have shown that these compounds have significant inhibitory effects on viruses such as PVX and ToCV, and have good development prospects. Attached Figure Description

[0026] Figure 1Fourier transform infrared spectrum of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1;

[0027] Figure 2 : The 1H NMR spectrum of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1;

[0028] Figure 3 Carbon spectrum of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1;

[0029] Figure 4 The effect of different concentrations on melon seed germination;

[0030] Figure 5 The effects of different compounds on melon seed germination;

[0031] Figure 6 Effects of different concentrations on the growth of melon seedlings;

[0032] Figure 7 The effects of different compounds on the growth of melon seedlings;

[0033] Figure 8 The effect of concentration on wheat seed resistance;

[0034] Figure 9 The effects of different compounds on wheat seed resistance;

[0035] Figure 10 : The amount of PVX virus mRNA accumulated in each group;

[0036] Figure 11 : The amount of ToCV virus mRNA accumulated in each group;

[0037] Figure 12 Chrono-coulometric curve of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1. Detailed Implementation

[0038] It should be noted that the following detailed descriptions are illustrative and intended to provide further explanation of this application. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application pertains.

[0039] As described in the background section, benzimidazole has bactericidal and antiviral effects, but it inhibits crop growth. Currently reported CO2 absorbents are mostly organic porous materials or amine absorbents; there are no reports of benzimidazole compounds absorbing CO2. Increased CO2 absorption by crops is beneficial to crop growth. If a benzimidazole compound capable of absorbing CO2 were designed, its application would provide both bactericidal and antiviral effects while also promoting growth in crops.

[0040] Based on this, the purpose of this invention is to provide a benzimidazole compound and its applications. During the synthesis of benzimidazole compounds, this invention discovered that benzimidazole compounds with the structure of Formula I can both kill bacteria and viruses and promote crop growth. Research has shown that the benzimidazole compounds prepared in this invention can absorb CO2, therefore it is speculated that the crop-promoting effect of the benzimidazole compounds prepared in this invention is also related to their CO2 absorption, thereby increasing the amount of CO2 absorbed by crops. However, CO2 absorption is not the only factor promoting crop growth; it is also related to the unique structure of the benzimidazole compounds. Furthermore, the antiviral effect of the benzimidazole compounds of this invention is superior to that of benzimidazole alone, indicating that both antiviral and crop-promoting effects are the result of multiple factors working together.

[0041] To enable those skilled in the art to better understand the technical solution of this application, the technical solution of this application will be described in detail below with reference to specific embodiments.

[0042] Note: The growth rate of each physiological indicator in the experimental case = (physiological indicator of the experimental group - physiological indicator of the CK group) / physiological indicator of the CK group × 100%; or the growth rate of each physiological indicator = (physiological indicator of the experimental group - physiological indicator of the blank group) / physiological indicator of the blank group × 100%.

[0043] The test materials used in the embodiments of this invention are all conventional test materials in the art and can be purchased through commercial channels.

[0044] Example 1: Preparation of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole

[0045] (1) Preparation of 5-nitrobenzimidazole: A 150 mL three-necked flask was used. 1.53 g of 4-nitro-o-phenylenediamine and 2.5 mL of formic acid were added, followed by 40 mL of 5 mol / L HCl solution. The mixture was heated to reflux using a serpentine condenser and reacted at 70 °C for 2 h. The solution was poured into a beaker, cooled to room temperature, and the pH was adjusted to 7 with 30% NaOH solution. The solution changed from red to yellow, and the flocculent material in the solution transformed into a yellow precipitate. The precipitate was placed in a 4 °C refrigerator for 12 h, then removed and filtered under reduced pressure. The product was dried in a 70 °C oven to obtain 5-nitrobenzimidazole with a yield of 62.8%. The synthetic route is as follows:

[0046] .

[0047] (2) Preparation of 2-bromo-5-nitro-1H-benzimidazole:

[0048] 2 g of 5-nitrobenzimidazole was dissolved in 30 mL of methanol to obtain a 5-nitrobenzimidazole solution, and 2 g of N-bromosuccinimide (NBS) was dissolved in 20 mL of methanol to obtain an NBS solution. After the 5-nitrobenzimidazole and NBS were completely dissolved in methanol, the 5-nitrobenzimidazole solution and the NBS solution were mixed together and heated at 60 °C. o The reaction was carried out at C for 1 hour. Then, rotary evaporation was performed, and the product was dried in a 50°C oven to give 2-bromo-5-nitro-1H-benzimidazole, with a yield of 38.6%. The synthetic route is as follows:

[0049] .

[0050] (3) Preparation of 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole: 2 g of 2-bromo-5-nitro-1H-benzimidazole, 1 g of phenothiazine, 2 g of acetonitrile, 2 g of anhydrous potassium carbonate, and 0.1 g of potassium iodide were added to 50 mL of DMF, heated and stirred, and reacted at 70 °C for 2 h. After the reaction was completed, the mixture was filtered while hot. The solvent was removed by rotary evaporation of the filtrate to obtain 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole, with a yield of 67.4%. The synthetic route is as follows:

[0051] .

[0052] Fourier transform infrared spectroscopy was performed on 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole, such as... Figure 1 As shown, the compound prepared in Example 1 was measured at 3459 cm⁻¹. -1 and 3339 cm -1There is a relatively obvious characteristic broad peak at 3046 cm⁻¹, which is mainly due to the stretching vibrations of NH₃ and CH₄; -1 The absorption peak at 1592 cm⁻¹ is produced by the stretching vibration of CH on the benzene ring. -1 The broad peak at 1471 cm⁻¹ is caused by the stretching vibration of the C=N double bond; -1 The absorption peak at 1300 cm⁻¹ is mainly produced by the stretching vibration of CN; -1 The absorption peak at 742 cm⁻¹ is mainly the absorption peak of -NO₂. -1 The absorption peak at that point is mainly the absorption peak of the benzene ring.

[0053] The 1H and 1C spectra of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole are shown below. Figures 2-3 As shown. 1 H-NMR(DMSO, 400Hz) δ: 10.20 (1H, s), 7.71 (2H, d), 7.61 (1H, s), 7.52(2H, d), 7.44~7.38(4H, m), 7.30(2H, d). 13 C-NMR (DMSO, 125Hz) δ: 156.12, 138.96, 138.67, 137.24, 132.70, 128.22, 127.34, 122.18, 112.46, 111.68, 110.34.

[0054] Example 2: Preparation of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole

[0055] The difference from Example 1 lies in step (2): 2g of 5-nitrobenzimidazole was dissolved in 30mL of DMF solution to obtain a 5-nitrobenzimidazole solution, and 2g of NBS was dissolved in 20mL of DMF to obtain an NBS solution. After the 5-nitrobenzimidazole and NBS were completely dissolved, the 5-nitrobenzimidazole solution and the NBS solution were mixed together and reacted at 60°C for 1h. Then, the solvent was removed by rotary evaporation, and the product was dried in an oven at 50°C to obtain 2-bromo-5-nitro-1H-benzimidazole with a yield of 43.9%.

[0056] 5-Nitro-2-(N-Phenothiazinyl)-1H-benzimidazole was finally prepared with a yield of 58.3%.

[0057] Example 3: Preparation of 5-(N-Phenothiazinyl)-1H-benzimidazole

[0058] 2 g of 5-bromo-1H-benzimidazole, 1 g of phenothiazine, 2 g of acetonitrile, 2 g of anhydrous potassium carbonate, and 0.1 g of potassium iodide were added to 50 mL of DMF, heated and stirred, and reacted at 70 °C for 2 h. After the reaction was complete, the mixture was filtered while hot. The solvent was removed by rotary evaporation of the filtrate to give 5-(N-phenothiazinyl)-1H-benzimidazole, with a yield of 46.4%. The synthetic route is as follows:

[0059] .

[0060] Example 4: Preparation of 2-bromo-5-amino-1H-benzimidazole

[0061] The difference from Example 1 lies in step (3):

[0062] (3) Preparation of 2-bromo-5-amino-1H-benzimidazole: 1 g of 2-bromo-5-nitro-1H-benzimidazole and 2 g of iron powder were added to a 50 mL round-bottom flask, followed by the slow addition of 20 mL of 5 mol / L hydrochloric acid solution. The round-bottom flask was placed in a 10-15℃ cold water bath to slow the reaction and prevent it from boiling violently during the addition of hydrochloric acid. When the solution in the round-bottom flask stopped boiling, the flask was placed in an 80℃ water bath and stirred for 1 h. After the reaction was complete, the mixture was filtered while hot. The solvent was removed by rotary evaporation of the filtrate to obtain 2-bromo-5-amino-1H-benzimidazole with a yield of 54.5%. The synthetic route is as follows:

[0063] .

[0064] Experiment 1: Germination Experiment of Melon Seeds

[0065] (1) Effect of concentration on melon seed germination

[0066] The 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole prepared in Example 1 was mixed with deionized water to prepare solutions with concentrations of 0, 0.1, 0.5, 1, 10, and 20 μg / mL, designated as the CK group, 0.1 μg / mL group, 0.5 μg / mL group, 1 μg / mL group, 10 μg / mL group, and 20 μg / mL group, respectively. Melon seeds were sterilized at 60°C for 20 min, with 30 seeds per group (3*10 parallel experiments were conducted). The melon seeds were then immersed in 50 mL of each of the above solutions at 28°C for 8 h.

[0067] The treated seeds from each group were placed in petri dishes, each dish placed on two sheets of moistened filter paper, and the seeds were covered with another sheet of filter paper. The dishes were then placed in an incubator in the dark to promote germination. The solutions and filter paper for each group were changed daily, and the dishes were rinsed. Germination occurred after 5 days. Five seeds from each group were selected for observation. Root length, stem length, number of lateral roots, fresh weight, and dry weight were measured using calipers and a weighing balance. The results are shown in Table 1 and Table 2. Figure 4 .

[0068] Table 1. Germination of melon seeds treated with different concentrations

[0069]

[0070] like Figure 4 As shown in Table 1, all physiological indicators of the seeds improved after treatment with the same concentration of solution. Overall, the 0.1 μg / mL solution showed the best effect. Compared with the control group (0 μg / mL), melon seeds cultured in 0.1 μg / mL 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution showed an 86% increase in average root length, a 290% increase in lateral root number, a 284% increase in stem length, a 198% increase in fresh biomass, and a 61% increase in dry weight. This indicates that 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution can improve various physiological indicators of seeds and promote seed germination.

[0071] (2) Effects of different compounds on melon seed germination

[0072] Benzimidazole, phenothiazine, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole prepared in Example 1 were respectively prepared with deionized water to form benzimidazole solution with a concentration of 0.1 μg / mL, phenothiazine solution with a concentration of 0.1 μg / mL, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution with a concentration of 0.1 μg / mL, and were respectively designated as Group I, Group II, and Group III, with deionized water as the blank group; the melon seeds were sterilized at 60℃ for 20 min, with 30 melon seeds in each group (3*10 parallel experiments were conducted).

[0073] The treatment and measurement of melon seeds in each group were the same as in (1) the effect of concentration on seed germination. Compared with the control group, the growth of root length, stem length, number of lateral roots, fresh weight and dry weight in groups I to III are shown in Table 2 and Figure 5 .

[0074] Table 2. Seed germination of melon under different treatments

[0075]

[0076] From Table 2 and Figure 5It can be seen that the growth rates of Group III are higher than those of Group I and Group II, and the growth rates of Group I are all negative, indicating that benzimidazole is not conducive to seed germination, while the 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1 has a better effect on the germination of melon seeds.

[0077] Experiment Example 2: Growth Promotion Experiment of Melon Seedlings

[0078] (1) Effect of concentration on the growth of melon seedlings

[0079] Five groups of solutions with concentrations of 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 2 were prepared with deionized water, resulting in concentrations of 0.1, 1, 5, 10, and 20 μg / mL. These were designated as the 0.1 μg / mL group, 1 μg / mL group, 5 μg / mL group, 10 μg / mL group, and 20 μg / mL group, with 0 μg / mL as the control group (CK). Each group contained 7 seedlings. 2 mL of each solution was evenly dripped onto the root of each seedling (a small hole was carefully made near the seedling root, and the solution was dripped in drop by drop through the hole). This was repeated every three days for a total of 10 days. The seedlings were grown in an incubator with a 24°C light exposure for 12 hours to simulate daytime, a 18°C ​​darkness exposure for 12 hours to simulate nighttime, and a humidity of 65%. After cultivation, the stem length, leaf area, and other physiological indicators of the melon were measured using a ruler and calipers. The results are shown in [Figure number missing]. Figure 6 And Table 3.

[0080] Table 3 Effects of different concentrations on seedling growth

[0081]

[0082] As shown in Figure 6 and Table 3, compared with the control group (0 μg / mL), the average stem length of melon seedlings cultured in 1 μg / mL 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution increased by 44%, and the leaf area increased by 35%. 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution can improve various physiological indicators of seedlings and promote seedling growth.

[0083] (2) Effects of different compounds on the growth of melon seedlings

[0084] Benzimidazole, phenothiazine, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole prepared in Example 1 were respectively prepared with deionized water to form benzimidazole solution, phenothiazine solution, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution with a concentration of 1 μg / mL. These were designated as Group I, Group II, and Group III, respectively, with deionized water as the blank group.

[0085] The experimental process and detection were the same as (1) the effect of concentration on seedling growth. Compared with the blank group, the growth of average stem length and leaf area in groups I to III is shown in Table 4 and Figure 7 .

[0086] Table 4. Seedling growth under different treatments

[0087]

[0088] From Table 4 and Figure 7 It can be seen that the growth rates of Group III are higher than those of Group I and Group II, while the growth rates of Group I are all negative, indicating that benzimidazole is not conducive to seedling growth, while the 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in Example 1 has a better effect on promoting the growth of melon seedlings.

[0089] Test Example 3: Salt and Alkali Resistance Test

[0090] (1) Effect of concentration on wheat seed resistance

[0091] Select plump wheat seeds and randomly divide 80 wheat seeds into two groups of 40 seeds each. The seeds were soaked in deionized water (control group) and 0.5 μg / mL 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole solution prepared in Example 1 for 8 h (experimental group).

[0092] Preparation of saline-alkali solution: Weigh 2.92 g NaCl and 2.10 g NaHCO3 and dissolve them in 500 mL of deionized water.

[0093] After soaking, wheat seeds from each group were placed on filter paper, seed side down, in petri dishes. A layer of filter paper was placed on top of the wheat seeds, and 4 mL of saline-alkali solution was added. The petri dishes were then covered and sealed with sealing film. They were incubated at 30 ℃ and 70% relative humidity for two days. After incubation, the number of germinated seeds was counted. Germination was defined as a sprout length exceeding half the seed length. The germination rate was recorded, and the dry and fresh weights of the seeds were measured. The results are shown in [Table missing]. Figure 8 .

[0094] like Figure 8 As shown, under saline-alkali conditions, the germination rate of wheat seeds in the control group was zero, while the germination rate of wheat seeds in the experimental group was 42%, with a 59% increase in fresh biomass and an 18% increase in dry weight. This indicates that 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole solution can promote the germination of wheat seeds under saline-alkali conditions.

[0095] (2) Effects of different compounds on wheat seed resistance

[0096] Benzimidazole, phenothiazine, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole prepared in Example 1 were respectively prepared with deionized water to form benzimidazole solution, phenothiazine solution, and 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution with a concentration of 0.5 μg / mL; these were designated as Group I, Group II, and Group III, respectively, with deionized water as the blank group.

[0097] The experimental process and detection were the same as in (1) the effect of concentration on resistance. The germination rate of wheat seeds in groups I to III, and the increase in fresh biomass and dry weight of groups I to III compared with the CK group are shown in Table 5. Figure 9 .

[0098] Germination rate = (Number of germinated wheat seeds / Total number of wheat seeds) × 100%.

[0099] Table 5. Germination of wheat seeds under different treatments

[0100]

[0101] From Table 5 and Figure 9 It can be seen that the wheat seeds in Group I and the control group did not germinate, with a germination rate of 0%, indicating that the wheat seeds treated with benzimidazole were not tolerant to salinity and alkalinity. The germination rate of wheat seeds in Group I was 27%, while nearly half of the wheat seeds treated with 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole in Group III germinated, indicating that 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole not only promotes seed germination but also enhances salt and alkali tolerance, thereby improving seed resistance.

[0102] Experiment Example 4: Antiviral Experiment

[0103] (1) Prepare 1 μg / mL benzimidazole solution, 1 μg / mL phenothiazine solution, and 1 μg / mL 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution using deionized water. Foliar spraying was performed on tobacco seedlings, with 1 mL sprayed per seedling. These were designated as the benzimidazole group, phenothiazine group, and compound group, with 5 seedlings sprayed in each group. Deionized water served as the blank control. 24 hours after spraying, Agrobacterium-mediated PVX (PVX No. 12183 in NCBI) was used as the pathogen, and the seedlings were infected by injection. Seven days after PVX infection, the third unfolded leaf was collected for testing. The mRNA accumulation of PVX virus was detected by quantitative real-time PCR, and the results are shown in [Figure 1]. Figure 10 The higher the accumulation of PVX virus mRNA, the greater the viral infection. It can be seen that the compound prepared in Example 1 has an inhibitory effect on the accumulation of PVX mRNA, and is superior to the benzimidazole group and the phenothiazine group.

[0104] (2) Prepare 1 μg / mL benzimidazole solution, 1 μg / mL phenothiazine solution, and 1 μg / mL 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole solution using deionized water. Foliar spraying was performed on tobacco seedlings, with 1 mL sprayed per seedling. These were designated as the benzimidazole group, phenothiazine group, and compound group, with 5 seedlings sprayed in each group. Deionized water served as the blank control. 24 hours after spraying, ToCV (ToCV No. 67754 in NCBI) mediated by Agrobacterium was used as the pathogen, and the seedlings were infected by injection. The third unfolded leaf was collected 14 days after ToCV infection for testing. The accumulation of ToCV mRNA was quantitatively detected by fluorescence. The results are shown in […]. Figure 11 It can be seen that among the compound groups, spraying significantly inhibited the accumulation of ToCV mRNA, and was superior to the benzimidazole group and the phenothiazine group.

[0105] Experiment 5: CO2 Adsorption Experiment

[0106] CO2 adsorption tests were conducted on the 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole prepared in Example 1. The specific procedure was as follows: 5 mg of 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole was dissolved in a perfluorosulfonic acid polymer solution (Nafion, purchased from Suzhou Shengernuo Technology Co., Ltd.), then coated onto conductive glass as the working electrode, a Pt mesh as the counter electrode, a saturated calomel electrode as the reference electrode, and 0.1 mol / L KHCO3 solution as the electrolyte. A CHI660D electrochemical workstation was connected for timed coulometric testing, and N2 or CO2 was continuously introduced into the electrolyte for 20 minutes. According to... Figure 12 The current signal response shows that the electrode exhibits a significant current signal response in a CO2 environment. According to Cottrell's theory: Q = nFG + Q dl +2nFAC 0 ox D 1 / 2 t 1 / 2 / Π 1 / 2 Total energy Q and t 1 / 2 The relationship is linear; in an N2 environment, the charge is Q. dl In a CO2 environment, the energy consumption is nFG+Q. dl The difference is nFG, therefore the adsorption capacity G of CO2 on the electrode material surface is 1.50 μmol / mg. This indicates that the 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole prepared in the example can adsorb CO2.

[0107] The above description is merely a preferred embodiment of this application and is not intended to limit this application. Various modifications and variations can be made to this application by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of this application should be included within the protection scope of this application.

Claims

1. A benzimidazole compound, characterized by, The benzimidazole compound is 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole, and its structural formula is: ； The 5-nitro-2-(N-phenthiazinyl)-1H-benzimidazole is prepared by the following method: (1) 4-nitro-o-phenylenediamine and formic acid were added to hydrochloric acid solution and heated under reflux. After the reaction was completed, the mixture was cooled to room temperature and the pH was adjusted to neutral to obtain a yellow precipitate. After drying, 5-nitrobenzimidazole was obtained. (2) Dissolve 5-nitrobenzimidazole and N-bromosuccinimide in organic solvents to obtain 5-nitrobenzimidazole solution and N-bromosuccinimide solution respectively. Mix 5-nitrobenzimidazole solution and N-bromosuccinimide solution to obtain 2-bromo-5-nitro-1H-benzimidazole. (3) Add 2-bromo-5-nitro-1H-benzimidazole, phenothiazine, acetonitrile, anhydrous potassium carbonate and potassium iodide to DMF, heat and stir to obtain 5-nitro-2-(N-phenothiazinyl)-1H-benzimidazole.

2. The benzimidazole compound according to claim 1, wherein In step (1), the ratio of the amount of 4-nitro-o-phenylenediamine, formic acid and hydrochloric acid solution added is 1.53 g: 2.5 mL: 40 mL; The concentration of the hydrochloric acid solution is 5 mol / L; the temperature of the reflux reaction is 60~80℃, and the reflux reaction time is 1~3h.

3. The benzimidazole compound according to claim 1, wherein In step (2), the organic solvent is DMF or methanol; the concentration of the 5-nitrobenzimidazole solution is 0.067 g / mL; the concentration of the N-bromosuccinimide solution is 0.1 g / mL; the volume ratio of the 5-nitrobenzimidazole solution to the N-bromosuccinimide solution is 3:2; and the mixing temperature is room temperature or 60°C.

4. The benzimidazole compound according to claim 1, wherein In step (3), the mass ratio of 2-bromo-5-nitro-1H-benzimidazole, phenothiazine, acetonitrile, anhydrous potassium carbonate and potassium iodide is 2:1:2:2:0.1; the ratio of the amount of 2-bromo-5-nitro-1H-benzimidazole added to DMF is 2g:50mL; the temperature of the heating reaction is 70℃ and the heating reaction time is 2h.

5. The use of the benzimidazole compounds according to any one of claims 1 to 4 in simultaneously promoting plant growth and resisting viruses.

6. Use according to claim 5, characterized in that, The plant growth promotion includes: promoting seed germination, promoting seedling growth, and improving seed salt and alkali tolerance; the virus is PVX virus and ToCV virus.

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