Cyclohexyl-containing quinoxaline derivative as well as preparation method and application thereof

Abstract

The invention relates to a cyclohexyl-containing quinoxaline derivative as well as a preparation method and application thereof, and the cyclohexyl-containing quinoxaline derivative is 3-cyclohexyl-1-methylquinoxaline-2 (1H)-ketone and is particularly suitable for inhibiting fusarium oxysporum. The derivative is prepared by an organic synthesis method which comprises the step of carrying out cyclization reaction on N-protected o-phenylenediamine and a carbonyl compound in the presence of trifluoroacetic acid. Experiments show that the compound has a remarkable antibacterial effect on fusarium oxysporum, and the minimum inhibitory concentration is 0.50 mg / mL. The derivatives can destroy the cell membrane structure of fusarium oxysporum and cause leakage of RNA, protein and reducing sugar in cells, so that the growth of thalli is inhibited. The invention provides a theoretical basis and an experimental basis for developing a novel efficient and low-toxicity bacteriostatic agent.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of bacteriostatic compound synthesis and agricultural disease control, and particularly relates to a quinoxaline derivative containing a cyclohexyl group and a preparation method and application thereof. BACKGROUND

[0002] Fusarium oxysporum is a widely distributed plant pathogenic fungus that can infect many economic crops such as sorghum, tomato and banana, causing wilt and root rot and leading to serious yield reduction. At present, the main control means is chemical pesticides, but long-term use leads to increased drug resistance and negative impact on the environment. Therefore, it is an urgent need to develop new types of efficient and low-toxicity bacteriostatic agents.

[0003] Quinoxaline derivatives are important nitrogen-containing heterocyclic compounds with the characteristics of strong structural modifiability and diverse biological activities. Some derivatives have been confirmed to have antibacterial, antifungal and other biological activities. Benzimidazole derivatives are also a class of heterocyclic compounds with wide biological activities and have good application prospects in the fields of pesticides and medicines. In the prior art, the synthesis of quinoxaline derivatives and benzimidazole derivatives depends on complex reaction conditions, and there are few studies on the bacteriostatic application of Fusarium oxysporum. There is no clear efficient bacteriostatic derivative and large-scale application technology. SUMMARY

[0004] The present application aims to provide a bacteriostatic agent and a preparation method thereof, and to expand its application in crop disease control.

[0005] In the first aspect, in order to achieve the above-mentioned purpose, the present application adopts the following technical scheme: a quinoxaline derivative containing a cyclohexyl group, which is 3-cyclohexyl-1-methyl quinoxaline-2(1H)-one, and its structural formula is as follows: .

[0006] In the second aspect, the present application further provides a preparation method of the quinoxaline derivative containing a cyclohexyl group, which is prepared according to the following synthesis route: .

[0007] In the third aspect, the present application further provides a bacteriostatic agent comprising the quinoxaline derivative containing a cyclohexyl group.

[0008] Further, the bacteriostatic agent further comprises 1-phenylmethyl-2-ethyl-5,6-difluoro-1 H -indole, and its structural formula is as follows: .

[0009] Further, the 1-phenylmethyl-2-ethyl-5,6-difluoro-1 H-Indole was prepared via the following synthetic route: .

[0010] Furthermore, the antibacterial agent also includes 1,6,7-trimethyl-3-propylquinoxalin-2(1H)-one, whose structural formula is as follows: .

[0011] Thirdly, the present invention also provides the application of the cyclohexyl-containing quinoxaline derivative or the antibacterial agent in inhibiting Fusarium oxysporum.

[0012] Furthermore, the cyclohexyl-containing quinoxaline derivative or antibacterial agent is used to control sorghum sickle stalk rot.

[0013] Furthermore, the concentration of the active ingredient of the cyclohexyl-containing quinoxaline derivative or antibacterial agent is 0.40-1.00 mg / mL.

[0014] The beneficial technical effects of this invention are: 1. During the research of this invention, various quinoxaline derivatives and benzimidazole derivatives were prepared. Cell leakage detection confirmed that the following compounds were selected: 3-cyclohexyl-1-methylquinoxaline-2(1H)-one (3d), 1,6,7-trimethyl-3-propylquinoxaline-2(1H)-one (3e), and 1-benzyl-2-ethyl-5,6-difluoro-1- ... H -Indole (5a) has very good inhibitory activity against the growth of Fusarium oxysporum. It can disrupt the cell membrane structure of Fusarium oxysporum, leading to the leakage of RNA, proteins and reducing sugars, thereby inhibiting cell growth.

[0015] 2. Compared with the prior art, the derivatives 3d, 3e, and 5a screened in this invention have the characteristics of strong antibacterial activity and clear mechanism of action, providing an experimental basis and theoretical support for the development of novel antibacterial agents.

[0016] The minimum inhibitory concentrations (MICs) for 3, 3d, 3e, and 5a are 0.50 mg / mL, 0.50 mg / mL, and 0.40 mg / mL, respectively. These concentrations are close to each other, which facilitates their combined use.

[0017] 4. Using substituted o-phenylenediamine and carbonyl compounds as raw materials, a cyclization reaction is carried out in acetonitrile solvent at room temperature under trifluoroacetic acid catalysis. The target derivative is then purified by liquid-liquid extraction, rotary evaporation, and column chromatography. This method features mild reaction conditions, simple operation, stable yield, and requires no high-temperature or high-pressure equipment.

[0018] 5. The structures of the target derivatives 3d, 3e, and 5a are highly modifiable and can be further optimized to obtain derivatives with lower toxicity and higher activity. At the same time, their antibacterial mechanism is unique and they are not likely to induce drug resistance in pathogens. They can be widely used in the prevention and control of Fusarium oxysporum diseases in various crops such as sorghum, tomato, and banana. Attached Figure Description

[0019] Figure 1 This is the standard curve for glucose.

[0020] Figure 2 The antibacterial effect of quinoxaline derivatives against Fusarium oxysporum.

[0021] Figure 3 This describes the antibacterial effect of benzimidazole derivatives against Fusarium oxysporum.

[0022] Figure 4 The minimum inhibitory concentration of the derivative was determined after 3 days.

[0023] Figure 5 The minimum inhibitory concentration (MIC) of derivative 3e was determined.

[0024] Figure 6 The minimum inhibitory concentration (MIC) of derivative 5a was determined.

[0025] Figure 7 The effect of derivative 3d on RNA leakage in Fusarium oxysporum.

[0026] Figure 8 The effect of derivative 3e on RNA leakage in Fusarium oxysporum.

[0027] Figure 9 The effect of derivative 3d on protein leakage in Fusarium oxysporum.

[0028] Figure 10 The effect of derivative 3e on protein leakage in Fusarium oxysporum.

[0029] Figure 11 The effect of derivative 3d on the leakage of reducing sugars in Fusarium oxysporum.

[0030] Figure 12 The effect of derivative 3e on the leakage of reducing sugars in Fusarium oxysporum.

[0031] Figure 13 The effect of derivative 5a on RNA leakage in Fusarium oxysporum.

[0032] Figure 14 The effect of derivative 5a on protein leakage in Fusarium oxysporum.

[0033] Figure 15 The effect of derivative 5a on the leakage of reducing sugars from Fusarium oxysporum. Detailed Implementation

[0034] The following detailed description illustrates the specific implementation method: I. Experimental Materials and Instruments Materials and reagents: Fusarium oxysporum was purchased from Beijing Bio-Biotech Co., Ltd.; 4,5-dimethyl-1,2-phenylenediamine, 4,5-difluoro-1,2-phenylenediamine, o-phenylenediamine, bromophenylmethyl, trifluoroacetic acid, acetonitrile, ethyl acetate, petroleum ether and other reagents were all commercially available analytical grade.

[0035] Instruments and equipment: Nuclear magnetic resonance spectrometer (AVANCE NEO 500), ultraviolet-visible spectrophotometer (UV-2600), rotary evaporator (N-1300), electric thermostatic incubator, clean bench, etc.

[0036] II. Preparation of Derivatives 1. Organic Synthesis of Five Quinoxaline Derivatives

[0037] Table 1 Organic Synthesis of Quinoxaline Derivatives

[0038] (1) Synthesis of intermediates 1a-1d (taking 1a as an example) Add 1.000 g of 4,5-difluoro-1,2-phenylenediamine and 1.300 g of iodomethane (weighed using an electronic balance) to a 50 mL round-bottom flask, followed by 1.000 g of sodium carbonate and 7 mL of [unclear - possibly a specific volume]. N,N -Dimethylformamide and a magnetic stirrer were used to react the mixture on a magnetic stirrer. A rubber stopper was inserted into the mouth of a round-bottom flask, ensuring a tight seal to prevent leakage. After 2 hours of reaction, liquid-liquid extraction was performed with ethyl acetate and water, and the organic phase was collected. Saturated brine was then added, and the organic phase was collected and dehydrated with anhydrous sodium sulfate. The organic phase was transferred to a round-bottom flask and the ethyl acetate solvent was removed using a rotary evaporator. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V), and the purification process was monitored by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, V / V), yielding 4,5-difluoro- N 1 -Methylbenzene-1,2-diamine (1a) 1b-1d were synthesized using a similar method.

[0039] (2) Synthesis of 3a-3e (taking 3a as an example) The 4,5-difluoro- obtained after the first step reaction N 1120 mg of toluene-1,2-diamine and 130 mg of ethyl dimethylpyruvate were added to a 25 mL round-bottom flask, followed by 2 mL of acetonitrile. After reacting for 2 minutes, 1 mL of (1M) trifluoroacetic acid and a magnetic stir bar were added, and the flask was placed on a magnetic stirrer for further reaction. A rubber stopper was inserted into the mouth of the round-bottom flask, ensuring a tight seal to prevent leakage. Simultaneously, a stainless steel needle was inserted into the rubber stopper, and a disposable syringe was attached to a balloon to form an oxygen supply device. The balloon was inflated as needed to ensure adequate oxygen supply. After 2 hours of reaction, liquid-liquid extraction was performed with ethyl acetate and water, and the organic phase was collected. Saturated brine was then added, and the organic phase was collected again, followed by dehydration with anhydrous sodium sulfate. The ethyl acetate solvent was removed by rotary evaporation in a round-bottom flask. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V), and the purification process was monitored by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, V / V), yielding 6,7-difluoro-3-isopropyl-1-methylquinoxaline-2 (1 H )-ketone (3a).

[0040] 3b-3e were synthesized using a similar method.

[0041] 2. Synthesis of two benzimidazole derivatives

[0042] Table 2 Organic Synthesis of Benzimidazole Derivatives

[0043] (1) Synthesis of 5a-5b (taking 5a as an example) Add 1.000 g of 4,5-difluoro-1,2-phenylenediamine and 1.300 g of bromophenylmethyl to a 50.0 mL round-bottom flask using an electronic balance, along with 1.000 g of sodium carbonate and 7.0 mL of [unspecified substance]. N,N Dimethylformamide and a magnetic stirrer were placed on a magnetic stirrer to react. A rubber stopper was then inserted into the neck of a round-bottom flask, ensuring a tight seal to prevent leakage. The product obtained after the first step of the reaction... N120 mg of 1-benzyl-4,5-difluoro-1,2-phenylenediamine and 100 mg of diethyl ketone alcohol were added to a 25.0 mL round-bottom flask, followed by 2.0 mL of acetonitrile. After reacting for 2 minutes, 0.7 mL of trifluoroacetic acid and a magnetic stir bar were added, and the flask was placed on a magnetic stirrer. A rubber stopper was inserted into the mouth of the round-bottom flask, ensuring a tight seal to prevent leakage. An air balloon was used to ensure oxygen supply. The organic phase was collected by liquid-phase extraction with ethyl acetate and water. Saturated brine was added, and the organic phase was collected and dehydrated with anhydrous sodium sulfate. The residue was transferred to a round-bottom flask and removed by rotary evaporation using a rotary evaporator. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate, V / V), with thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, V / V) used to monitor the purification process, yielding 1-benzyl-2-ethyl-5,6-difluoro-1-phenylenediamine. H -Indole (5a).

[0044] 5b was synthesized using a similar method.

[0045] III. Antibacterial Test (I) Preparation of bacterial suspension Fusarium oxysporum was inoculated onto potato dextrose agar (PDA) medium and activated by culturing at 30°C for 3 days. Single colonies were then picked and inoculated onto potato dextrose liquid medium and cultured at 30°C and 200 r / min for 48 h to prepare a bacterial suspension.

[0046] (II) Preparation of antibacterial agents at different concentrations The target compound at a concentration of 2.00 mg / mL was diluted using ethanol as the solvent to obtain concentrations of 0.25, 0.50, 0.75, and 1.00 mg / mL, which were then used as antibacterial solutions.

[0047] (ii) Antibacterial activity test Fusarium oxysporum was cultured until the bacterial suspension turned purple. 100 μL of the bacterial suspension was evenly spread onto the surface of a solid culture medium and allowed to stand for 5-10 minutes until the surface was slightly dry. Sterile blank antimicrobial susceptibility testing discs (6 mm in diameter) were picked up with sterile forceps and gently placed on the surface of the culture medium with the bacterial suspension spread. The discs were evenly distributed on each medium, ensuring equal spacing. The discs were gently pressed with sterile forceps to ensure full contact with the medium. A suitable amount of the test sample was then pipetted onto the disc. The control group used an ethanol solution, and the experimental group used a mixed ethanol solution of 3a-3e, 5a, and 5b. The culture dishes were incubated upright at 30 °C for 48 h. The quinoxaline derivatives with antibacterial effects were then identified.

[0048] The filter paper disc method was used: 100 μL of bacterial suspension was evenly spread on a PDA plate, and sterile filter paper discs soaked with different concentrations of target derivative solutions were attached to the surface of the plate. The plate was incubated at 30°C for 48 h, and the formation of inhibition zones was observed.

[0049] (III) Detection of cell leakage 1. Detection of RNA and protein leakage Fusarium oxysporum was cultured in liquid culture for 48 h until the bacterial suspension turned purple. 20 mL of the bacterial suspension was aliquoted into each centrifuge tube and centrifuged at 5000 r / min for 30 min. After washing twice with sterile physiological saline, 20 mL of physiological saline was added. Different concentrations of quinoxaline derivatives were added to the bacterial suspension. The final concentrations for 3d were 0, 0.50, and 1.00 mg / mL, and for 3e were 0, 0.50, and 1.00 mg / mL. The suspension was incubated in a constant temperature shaker at 30 ℃ and 200 r / min. 1 mL of the bacterial suspension was collected after 1, 2, 3, 4, 6, 8, and 10 h, centrifuged at 10000 r / min for 10 min, and the supernatant was retained for cryopreservation. The supernatant was diluted 4-fold, and each sample was tested in triplicate. The absorbance of the supernatant was measured at 260 nm and 280 nm using a UV-Vis spectrophotometer, and the corresponding curves were plotted.

[0050] 2. Detection of reducing sugar leakage 20 mL of bacterial suspension was evenly dispensed into each centrifuge tube and centrifuged at 5000 r / min for 30 min. The tubes were washed twice with sterile physiological saline and then 20 mL of physiological saline was added. Different concentrations of quinoxaline derivatives were weighed and added to the bacterial suspension. The final concentrations for 3d were 0, 0.50, and 1.00 mg / mL, and the final concentrations for 3e were 0, 0.50, and 1.00 mg / mL. The tubes were incubated in a constant temperature shaker at 30 ℃ and 200 r / min. 1 mL of bacterial suspension was collected after 1, 2, 3, 4, 6, 8, and 10 h, and centrifuged at 10000 r / min for 10 min. The supernatant was retained and frozen for preservation. The supernatant was diluted 4-fold. 2 mL of the diluted supernatant and 1 mL of DNS reagent were mixed and heated in boiling water for 5 min. The mixture was then brought to the 15 mL mark with deionized water, cooled to room temperature, and incubated at 540 nm. The absorbance was measured at the absorbance value, and three parallel tests were performed on each sample. The reducing sugar content was obtained by using the absorbance-glucose content standard curve, and the corresponding curve was plotted.

[0051] 3. Drawing the glucose standard curve Take 0, 0.2, 0.4, 0.6, 0.8, and 1.0 mL of glucose standard solution (1 mg / mL) into 25 mL stoppered colorimetric tubes, respectively, and bring the volume to 2 mL with deionized water. Add 1 mL of DNS reagent to each tube, heat in a boiling water bath for 5 min, cool to room temperature, and bring the volume to the 15 mL mark with deionized water. Measure the absorbance at 540 nm for analysis, using deionized water as a control. Perform regression analysis by plotting a scatter plot with glucose concentration (mg) as the independent variable (x-axis) and absorbance as the dependent variable (y-axis). Figure 1 As shown, the regression equation for the glucose standard curve is y = 0.6401x - 0.0026, and the correlation coefficient R is [missing value]. 2 =0.9992, indicating a good correlation.

[0052] IV. Antibacterial effect 1. Preliminary screening of antibacterial effects Bacterial suspensions were prepared by liquid culture, and their antibacterial effects were determined using the filter paper disc method. Control and experimental groups were set up, and inhibition zones were observed to evaluate the inhibitory ability of five quinoxaline derivatives against *Fusarium oxysporum*. The antibacterial results of the target compounds 3a-3e using the filter paper disc method are shown below. Figure 2 As shown, ethanol does not exhibit antibacterial activity against Fusarium oxysporum, and 3a-3c do not show any antibacterial activity against Fusarium oxysporum. However, 3d-3e show relatively significant antibacterial effects against Fusarium oxysporum. Based on this preliminary screening, 3d-3e, which showed significant antibacterial effects, were further investigated to determine their minimum inhibitory concentrations (MICs).

[0053] The antibacterial results of the target compounds 5a-5b were also tested using filter paper discs, as shown in the following figures. Figure 3 As shown, ethanol has no antibacterial activity against Fusarium oxysporum, and 5b has no antibacterial effect against Fusarium oxysporum, while 5a has a more significant antibacterial effect against Fusarium oxysporum. 5a, which showed significant antibacterial effect, was preliminarily screened for further determination of its minimum inhibitory concentration (MIC). 2. Antibacterial Experiment The target compound at a concentration of 2 mg / mL was diluted using the dilution method, and the minimum inhibitory concentration (MIC) at 3 days was determined using the filter paper disc method. Figure 4 As shown, the minimum inhibitory concentration of 3e is as follows: Figure 5 As shown.

[0054] Table 3 Determination of Minimum Inhibitory Concentration

[0055] Note: "+" indicates no inhibition zone, "-" indicates the presence of an inhibition zone. Table 3 shows that at a concentration of 0.50 mg / mL, inhibition zones began to appear for 3d, and the size of the inhibition zones increased significantly with increasing concentration. Similarly, at a concentration of 0.50 mg / mL, inhibition zones also began to appear for 3e, and the size of the inhibition zones increased significantly with increasing concentration. This indicates that the minimum inhibitory concentrations (MICs) for 3d and 3e against *Fusarium oxysporum* are 0.50 mg / mL and 0.50 mg / mL, respectively. Both 3d and 3e exhibit good antibacterial effects against *Fusarium oxysporum*, but the inhibitory effect of 3e is significantly stronger than that of 3d.

[0056] The target compound at a concentration of 2.0 mg / mL was diluted using the dilution method, and the minimum inhibitory concentration (MIC) for 5 years was determined using the filter paper disc method. Figure 6 As shown.

[0057] Table 4 Determination of Minimum Inhibitory Concentration

[0058] Note: "+" indicates no inhibition zone, "-" indicates the presence of an inhibition zone. Depend on Figure 6 As shown in Table 4, an inhibition zone begins to appear at a concentration of 0.4 mg / mL for 5a, and the size of the inhibition zone increases significantly with increasing concentration. This indicates that the minimum inhibitory concentration of 5a against Fusarium oxysporum is 0.4 mg / mL.

[0059] 3. Determination of intracellular leakage of Fusarium oxysporum (1) Leakage of RNA and protein from Fusarium oxysporum by quinoxaline derivatives The effects of 3d and 3e treatments on RNA leakage in Fusarium oxysporum are shown in [reference needed]. Figure 7 and Figure 8 The effects of 3d and 3e treatments on protein leakage in Fusarium oxysporum are shown in [reference needed]. Figure 9 and Figure 10 .

[0060] Ribosomes, important structures within Fusarium oxysporum cells, are composed of RNA and protein. Their function is to mediate protein biosynthesis, making these two molecules crucial for normal cellular life activities. RNA and protein exhibit maximum absorbance at wavelengths of 260 nm and 280 nm, respectively. Based on this characteristic, the presence of RNA and protein in extracellular physiological saline can be detected by ultraviolet-visible spectrophotometry, thereby assessing cell membrane integrity.

[0061] Experimental results showed that different concentrations of quinoxaline derivatives 3d and 3e significantly affected the leakage of RNA and proteins from *Fusarium oxysporum*. At the same treatment time, the absorbance values ​​at 260 nm and 280 nm increased with increasing concentrations of 3d or 3e, indicating that both compounds increased cell membrane permeability, leading to the leakage of intracellular RNA and proteins. Furthermore, under the same concentration conditions, the absorbance value increased with prolonged treatment time, further confirming the continuous progression of cell membrane damage.

[0062] As shown in the figure above, at a concentration of 0.50 mg / mL, the absorbance of the 3e treatment group was significantly higher than that of the 3d treatment group, indicating that 3e induced more severe RNA and protein leakage. This result suggests that, compared to 3d, the quinoxaline derivative 3e has a stronger disruptive effect on the Fusarium oxysporum cell membrane. Preliminary assessment indicates that the quinoxaline derivative induces RNA and protein leakage by disrupting the integrity of the Fusarium oxysporum cell membrane, ultimately leading to cell inhibition. Its antibacterial effect requires a relatively long time to take effect.

[0063] (2) Leakage of reducing sugars from Fusarium oxysporum by quinoxaline derivatives The effects of 3d and 3e treatments on the leakage of reducing sugars in Fusarium oxysporum are shown in the figure. Figure 11 and Figure 12 .

[0064] When the absorbance of the supernatant was measured at 260 nm and 280 nm, cell surface substances naturally leaked out. Therefore, the assessment of cell membrane integrity could be achieved by detecting the degree of leakage of intracellular reducing sugars, which provides an effective indicator for evaluating the disruptive effects of quinoxaline derivatives 3d and 3e on Fusarium oxysporum.

[0065] Compared with the control group, the reducing sugar content in samples treated with 3d and 3e was significantly increased. Within 10 h, the leakage of reducing sugar showed a clear dose-dependent increasing trend with the increase of 3d and 3e concentrations. Under the same concentration of 0.50 mg / mL, the reducing sugar content in the supernatant of the bacterial suspension treated with 3e was significantly higher than that in the 3d treatment group.

[0066] (3) The amount of RNA and protein leakage in Fusarium oxysporum cells caused by benzimidazole derivatives The effect of 5a treatment on RNA leakage in Fusarium oxysporum is shown in the figure. Figure 13 The effect of 5a treatment on protein leakage in Fusarium oxysporum is shown in [reference needed]. Figure 14 .

[0067] As shown in the figure, the leakage of RNA and protein from *Fusarium oxysporum* varied among different concentrations of the 5a treatment group. At the same time point, the absorbance increased with increasing concentration, indicating a greater leakage of both RNA and protein, suggesting that higher concentrations resulted in better inhibition of *Fusarium oxysporum*. Similarly, at the same concentration, the absorbance continuously increased with treatment time, indicating that RNA and protein continuously leached from the cell membrane, slowing the inhibitory effect. At the same time point and concentration, the 5a treatment group showed a greater leakage of protein than RNA. Preliminary conclusions suggest that benzimidazole derivatives also disrupted the *Fusarium oxysporum* cell membrane, triggering RNA and protein leakage, ultimately leading to cell inhibition. In summary, benzimidazole derivatives exert their antibacterial effect faster than quinoxaline derivatives.

[0068] (4) The effect of benzimidazole derivatives on the leakage of reducing sugars in Fusarium oxysporum cells The effect of 5a treatment on reducing sugar leakage in Fusarium oxysporum is shown in the figure. Figure 15 .

[0069] The extent of damage to the cell surface by 5α was reflected by measuring the leakage of intracellular reducing sugars. Figure 15 It was found that, compared with the control group, the reducing sugar content in the 5a treatment group was significantly increased. Furthermore, within the same time frame, the reducing sugar content increased significantly with increasing concentration, showing a clear upward trend within 2 hours, indicating a relatively rapid inhibitory effect.

[0070] The above descriptions are merely embodiments of the present invention, and common knowledge such as specific technical solutions and / or characteristics are not described in detail here. It should be noted that those skilled in the art can make various modifications and improvements without departing from the technical solutions of the present invention, and these should also be considered within the scope of protection of the present invention. These modifications and improvements will not affect the effectiveness of the implementation of the present invention or the practicality of the patent. The scope of protection claimed in this application should be determined by the content of its claims, and the specific embodiments described in the specification can be used to interpret the content of the claims.

Claims

1. A quinoxaline derivative containing a cyclohexyl group, characterized in that: The cyclohexyl-containing quinoxaline derivative is 3-cyclohexyl-1-methylquinoxaline-2(1H)-one, and its structural formula is as follows: 。 2. The method for preparing the cyclohexyl-containing quinoxaline derivative according to claim 1, characterized in that: Prepared according to the following synthetic route: 。 3. An antibacterial agent, characterized in that, Including the cyclohexyl-containing quinoxaline derivatives as described in claim 1.

4. The antibacterial agent according to claim 3, characterized in that, It also includes 1-benzyl-2-ethyl-5,6-difluoro-1 H -Indole, the 1-benzyl-2-ethyl-5,6-difluoro-1 H The structural formula of indole is as follows: 。 5. The antibacterial agent according to claim 3, characterized in that, It also includes 1,6,7-trimethyl-3-propylquinoxalin-2(1H)-one, whose structural formula is as follows: 。 6. The antibacterial agent according to claim 4, characterized in that, The 1-benzyl-2-ethyl-5,6-difluoro-1 H -Indole was prepared via the following synthetic route: 。 7. The use of the cyclohexyl-containing quinoxaline derivative according to claim 1 or the antibacterial agent according to any one of claims 3 to 6 in inhibiting Fusarium oxysporum.

8. The application according to claim 7, characterized in that: The quinoxaline derivatives or antibacterial agents containing cyclohexyl groups are used to control sorghum sickle stalk rot.

9. The application according to claim 8, characterized in that: The effective ingredient concentration of the cyclohexyl-containing quinoxaline derivative or antibacterial agent is 0.40-1.00 mg / mL.

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