Preparation method and application of naphthyl methylamino ethyl ester

Abstract

The invention discloses a preparation method and application of naphthyl methylaminoethyl ester in the technical field of plant growth stimulants, and the naphthyl methylaminoethyl ester is prepared by taking naphthylacetic acid and N, N-dimethylethanolamine as raw materials through one-step synthesis. The synthesis method is simple, the solvent can be recycled, the influence of the solvent on the environment can be reduced, meanwhile, the production cost is reduced, the process is simple, green and environment-friendly, the yield is high, the product performance is stable, and a new research direction is provided for high-quality green development of ecological agriculture.

Description

Technical Field

[0001] The invention belongs to the technical field of plant growth stimulants, and specifically refers to a preparation method and application of naphthylaminoethyl ester, which can effectively promote the growth of corn plants, significantly promote the growth of corn roots, and achieve the effect of stimulating crop growth. Background Art

[0002] Plant growth stimulants play a positive role in controlling seed germination and dormancy, promoting rooting, enhancing stress resistance including disease resistance, drought resistance, salt resistance, and frost resistance, regulating endogenous hormones, improving the taste of fruits, and promoting the ability to absorb fertilizers. For example, endogenous active substances are often called plant hormones, such as auxins, gibberellins, cytokinins, etc., which can well regulate plant growth and various fruit indicators, while non-endogenous external active substances are called plant growth stimulants; corn is a widely grown food crop rich in starch, fiber, vitamin B and minerals, which makes it an important source of energy. During the growth of corn plants, plant growth stimulants Stimulants, like sunlight, temperature, water and other nutrients, play an important role in plant growth. By adding plant growth stimulants, the growth of corn plants can be effectively promoted, the growth of corn crop roots can be significantly promoted, and the biomass of plants can be increased. At present, most of the plant growth regulators used are artificial synthetic compounds, which usually involve multiple steps and require precise control conditions, making the synthesis process complicated. At the same time, harmful by-products may be produced during the production process, causing pollution to the environment. Therefore, it is very necessary to develop a plant growth stimulant with a simple synthesis method and no pollution, in order to protect the environment, improve the quality of agricultural products and ensure food safety.

[0003] The existing technologies currently have the following main problems: the synthesis process of plant growth stimulants is complex, easily pollutes the environment, and the product effect is poor. Summary of the invention

[0004] In view of the above situation, in order to overcome the defects of the prior art, the present invention provides a preparation method and application of naphthylaminoethyl ester, using naphthylacetic acid and N,N-dimethylethanolamine as raw materials, and obtaining a compound capable of stimulating corn growth through a one-step synthesis. The synthesis method is simple, the solvent can be recycled, and the impact of the solvent on the environment can be reduced, while reducing production costs. The process of the present invention is simple, green and environmentally friendly, the yield is high and the product performance is stable; it provides a new direction for the high-quality green development of agriculture.

[0005] In order to achieve the above object, the present invention proposes a naphthylaminoethyl ester, whose structural formula is: .

[0006] The present invention also provides a method for preparing the naphthylaminoethyl ester, which specifically comprises the following steps: S1, using naphthylacetic acid and N,N-dimethylethanolamine as raw materials, toluene as solvent, 98wt% concentrated sulfuric acid as catalyst, heating reflux stirring reaction; S2, after the reaction is completed, transfer to a rotary evaporator while hot and perform vacuum distillation to obtain naphthylaminoethyl ester, which is then recycled and reused after solvent recovery; Preferably, in S1, the molar ratio of naphthylacetic acid to N,N-dimethylethanolamine is 1:1.3-1.4.

[0007] Further, in S1, the heating reflux stirring reaction is carried out at a temperature of 120-130° C. and a time of 6-7 hours.

[0008] Furthermore, in S2, the reduced pressure distillation is carried out at a temperature of 66-76°C for a time of 1-1.5 hours.

[0009] The present invention also provides the application of the naphthylaminoethyl ester, which can be used as a plant growth stimulant. The concentration of the plant growth stimulant is 5-40 ppm.

[0010] Preferably, when used as a plant growth stimulant, the selected plant is corn.

[0011] Furthermore, when used as a plant growth stimulant, the specific use method is at least one of seed soaking, root irrigation, and leaf spraying; Furthermore, when used as a plant growth stimulant, the concentration used for seed soaking is 10-40 ppm; the concentration used for root irrigation is 5-20 ppm; and the concentration used for spraying is 20-30 ppm.

[0012] The beneficial effects achieved by the present invention are as follows: the naphthylaminoethyl ester prepared by the present invention can effectively promote the growth of corn plants, significantly promote the growth of corn roots, and increase the biomass of plants. The present invention uses naphthylacetic acid and N,N-dimethylethanolamine as raw materials, toluene as a solvent, and concentrated sulfuric acid as a catalyst to prepare the naphthylaminoethyl ester through a one-step synthesis method. The synthesized naphthylaminoethyl ester has the advantages of good stability, low dosage, low toxicity, simple production process, and no pollution to the environment, and can be widely used as a plant growth stimulant. BRIEF DESCRIPTION OF THE DRAWINGS

[0013] Figure 1 The reaction flow chart for preparing naphthylaminoethyl ester in Example 1; Figure 2 The high resolution mass spectrum of naphthylaminoethyl ester prepared in Example 1; Figure 3 This is a comparison chart of the hydroponic growth promotion of corn using naphthylaminoethyl ester prepared in Example 1.

[0014] The accompanying drawings are used to provide further understanding of the present invention and constitute a part of the specification. They are used to explain the present invention together with the embodiments of the present invention and do not constitute a limitation of the present invention. DETAILED DESCRIPTION

[0015] The technical solutions in the embodiments of the present invention will be clearly and completely described below in conjunction with the drawings in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, rather than all the embodiments; based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention.

[0016] Unless otherwise defined, all professional and scientific terms used herein have the same meanings as those familiar to those skilled in the art. In addition, any methods and materials similar or equivalent to those described herein may be applied to the present invention. The preferred implementation methods and materials described herein are for demonstration purposes only and are not intended to limit the content of this application.

[0017] The experimental methods in the following examples are conventional methods unless otherwise specified; the experimental materials used in the following examples are purchased from commercial channels unless otherwise specified.

[0018] Embodiment 1: Figure 1 The reaction flow chart of Example 1 for preparing naphthylethylaminoethyl ester is shown as follows; as shown in the figure, naphthylethylaminoethyl ester is synthesized from naphthylacetic acid and N,N-diethylethanolamine in one step, the process is simple, and the preparation method specifically comprises the following steps: 5.0 g (26.85 mmol) of naphthylacetic acid and 3.28 g (36.78 mmol) of N,N-diethylethanolamine were added to a 250 mL three-necked flask, followed by 60 mL of toluene, and 0.5 ml of 98 wt% concentrated sulfuric acid was added dropwise. A rotor was placed and a condenser was connected. The mixture was heated to reflux at 120 °C with stirring for 6 hours. After the reaction was completed, the mixture was transferred to a rotary evaporator while hot and distilled at 70 °C under reduced pressure for 1 hour to obtain 4.368 g of a brown-yellow oily liquid with a yield of 90.2%.

[0019] Figure 2 This is a high-resolution mass spectrum of naphthylethylaminoethyl ester prepared in Example 1; as shown in the figure, the peak at 258.1492 in the mass spectrum corresponds to the [M+H]+ peak of naphthylethylaminoethyl ester.

[0020] Example 2: 5.0 g (26.85 mmol) of naphthylacetic acid and 3.11 g (34.90 mmol) of N,N-diethylethanolamine were added to a 250 mL three-necked flask, followed by 60 mL of toluene, 0.5 ml of 98 wt% concentrated sulfuric acid was added dropwise, a rotor was put into the condenser, and the mixture was heated to reflux at 120 ° C with stirring for 6 hours. After the reaction was completed, the mixture was transferred to a rotary evaporator while hot, and distilled at 66 ° C under reduced pressure for 1 h to obtain 4.368 g of a brown oily liquid with a yield of 86.3%.

[0021] Example 3: 5.0 g (26.85 mmol) of naphthylacetic acid and 3.35 g (37.59 mmol) of N,N-diethylethanolamine were added to a 250 mL three-necked flask, followed by 60 mL of toluene, 0.5 ml of 98 wt% concentrated sulfuric acid was added dropwise, a rotor was put into the condenser, and the mixture was heated to reflux at 130 ° C with stirring for 7 hours. After the reaction was completed, the mixture was transferred to a rotary evaporator while hot and distilled at 76 ° C under reduced pressure for 1.5 h to obtain 4.368 g of a brown oily liquid with a yield of 89.1%.

[0022] Example 4: 5.0 g (26.85 mmol) of naphthylacetic acid and 3.23 g (36.25 mmol) of N, N-diethylethanolamine were added to a 250 mL three-necked flask, followed by 60 mL of toluene, 0.5 ml of 98 wt% concentrated sulfuric acid was added dropwise, a rotor was put into the condenser, and the mixture was heated to reflux at 125 ° C with stirring for 6.5 hours. After the reaction was completed, the mixture was transferred to a rotary evaporator while hot and distilled at 70 ° C under reduced pressure for 1.25 h to obtain 4.368 g of a brown oily liquid with a yield of 89.6%.

[0023] Experimental example: 1. Corn seed germination experiment The naphthylaminoethyl ester and naphthylacetic acid prepared in Example 1 were respectively prepared into 10ppm, 20ppm, and 40ppm standard solutions, and 15 corn seeds were soaked with 10ppm, 20ppm, and 40ppm naphthylacetic acid solutions and naphthylaminoethyl ester, respectively, and 15 corn seeds were treated with clean water as a control. After 3 days, the germination rate was observed and counted.

[0024] Germination rate (%) = (number of test seeds germinated after 3 days / total number of test seeds) × 100%.

[0025] Experimental results analysis: Table 1 shows the germination rate of corn seeds treated with different concentrations of naphthylaminoethyl ester and naphthylacetic acid:

[0026] As can be seen from Table 1, compared with pure water, different concentration gradients of naphthylacetic acid and naphthylaminoethyl ester compounds have a significant promoting effect on the germination of corn seeds. The germination rate of 10ppm naphthylaminoethyl ester treatment increased by 63% compared with the pure water treatment. Soaking corn seeds with naphthylaminoethyl ester at a low concentration level can have a good germination-promoting effect.

[0027] 2. Corn hydroponic growth promotion experiment After the corn seeds are disinfected, they are placed in a culture dish covered with filter paper, clean sterile cotton is moistened and placed on the filter paper, 10 mL of sterile water is added to keep the seeds moist, and then the culture dish is placed in a constant temperature incubator at 28° C. to ensure that the seeds can germinate normally; after the seeds germinate, corns with the same growth potential are selected and transplanted into a seedling tray, and when the first true leaf begins to unfold, the naphthylaminoethyl ester and naphthylacetic acid prepared in Example 1 are respectively prepared into 5 ppm, 10 ppm, and 20 ppm standard solutions for root irrigation, and the plant height, root length, plant weight, root weight and other data are observed and measured after 14 days.

[0028] Table 2 shows the experimental data of corn treated with different solution concentrations:

[0029] The results can be seen from Table 1: from the comparison analysis of plant height, root length, root fresh weight, root dry weight and plant weight data with the control, in general, 5ppm of naphthylaminoethyl ester has a better effect; compared with the data of the control group of pure water, the application of 5ppm of naphthylacetic acid solution increased the root fresh weight by 38% and the root dry weight by 47.9%; the application of 5ppm of naphthylaminoethyl ester increased the root fresh weight by 90.6% and the root dry weight by 125%.

[0030] Figure 3 This is a comparison chart of the hydroponic growth promotion of corn by naphthylaminoethyl ester prepared in Example 1, wherein A is the hydroponic growth promotion of corn by naphthylacetic acid, B is the hydroponic growth promotion of corn by naphthylaminoethyl ester, 1 is the clear water group, 2-4 has a naphthylacetic acid content of 5ppm, 10ppm, and 20ppm, 5-7 has a naphthylaminoethyl ester content of 5ppm, 10ppm, and 20ppm in the hydroponic culture solution, and 5ppm naphthylacetic acid and 5ppm naphthylaminoethyl ester have obvious growth-promoting effects. The root growth of 5ppm naphthylaminoethyl ester is significantly better than that of the clear water group, and is better than 5ppm naphthylacetic acid in terms of root fresh weight and root dry weight, and has excellent performance in increasing plant biomass using low-concentration products.

[0031] While the embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that many changes, modifications, substitutions and variations can be made to the embodiments without departing from the principles and spirit of the invention.

[0032] The present invention and its implementation methods are described above, which is not restrictive. The drawings are only one of the implementation methods of the present invention, and the actual application is not limited thereto. In short, if ordinary technicians in the field are inspired by it and design methods and embodiments similar to the technical solution without creativity without departing from the purpose of the invention, they should all fall within the protection scope of the present invention.

Claims

1. A naphthylaminoethyl ester, characterized in that The naphthylaminoethyl ester is synthesized from naphthylacetic acid and N,N-dimethylethanolamine in one step, and its structural formula is: ； The preparation method of naphthylaminoethyl ester comprises: S1, using naphthylacetic acid and N,N-dimethylethanolamine as raw materials, toluene as solvent, 98wt% concentrated sulfuric acid as catalyst, heating reflux stirring reaction; S2. After the reaction is completed, transfer the mixture to a rotary evaporator while hot and perform reduced pressure distillation to obtain naphthylaminoethyl ester, and the solvent is recovered and reused.

2. A method for preparing naphthylaminoethyl ester according to claim 1, characterized in that: include: S1, using naphthylacetic acid and N,N-dimethylethanolamine as raw materials, toluene as solvent, 98wt% concentrated sulfuric acid as catalyst, heating reflux stirring reaction; S2. After the reaction is completed, transfer the mixture to a rotary evaporator while hot and perform reduced pressure distillation to obtain naphthylaminoethyl ester, and the solvent is recovered and reused.

3. The preparation method of naphthylaminoethyl ester according to claim 2, wherein: In S1, the molar ratio of naphthylacetic acid to N,N-dimethylethanolamine is 1:1.3-1.

4.

4. The preparation method of naphthylaminoethyl ester according to claim 2, wherein: In S1, the heating reflux stirring reaction is performed at a temperature of 120-130° C. and a reaction time of 6-7 hours.

5. The method for preparing naphthylaminoethyl ester according to claim 2, wherein: In S2, the reduced pressure distillation is carried out at a temperature of 70-80°C for 1-1.5 hours.

6. An application of naphthylaminoethyl ester according to claim 1, characterized in that: The naphthylaminoethyl ester is used as a plant growth stimulant, and the concentration of the plant growth stimulant is 5-40 ppm.

7. The use of naphthylaminoethyl ester according to claim 6, characterized in that: When the naphthylaminoethyl ester is used as a plant growth stimulant, the selected plant is corn.

8. The use of naphthylaminoethyl ester according to claim 6, characterized in that: When the naphthylaminoethyl ester is used as a plant growth stimulant, the specific use method is at least one of seed soaking, root irrigation, and leaf spraying; the concentration used for seed soaking is 10-40ppm; the concentration used for root irrigation is 5-20ppm; the concentration used for spraying is 20-30ppm.

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