Preparation method and application of naphthyl oxygen bis-aminomethyl ester compound

Abstract

The invention discloses the technical field of plant growth stimulants, and particularly relates to a preparation method and application of a compound of naphthyl oxygen bis-aminomethyl ester. Naphthyloxyacetic acid and N, N-dimethylaminoethanol are used as raw materials to obtain the target product naphthyloxybis (aminomethyl) ester. And carrying out reduced pressure distillation to obtain a plant growth stimulant product. The method is simple in process and high in yield; and the used solvent can be recycled, is green and pollution-free, and does not involve emission of three wastes. The plant growth stimulant not only has the characteristics of safety, no toxicity, strong activity, promotion of plant growth, promotion of crop rooting, increase of crop yield and the like, but also has the advantages of quality improvement, efficiency improvement, good action effect and the like. The naphthyloxy bis-aminomethyl ester compound prepared by the invention can be applied to corn as a plant growth stimulant, can promote the growth of corn plants, and can also significantly promote the growth of corn roots. The naphthyloxy bis-aminomethyl ester compound prepared by the invention has the advantages of high stability, small dosage, no toxicity and harmlessness, promotion of crop growth and the like. Therefore, the plant growth stimulant provides a new research direction for agricultural green development, and has a good application prospect.

Description

Technical Field

[0001] The invention belongs to the field of plant growth stimulants, and specifically relates to a preparation method and application of a naphthoxybisaminomethyl ester compound, which can effectively promote the growth of corn plants and significantly promote the growth of corn roots, thereby stimulating the growth of crops. Background Art

[0002] In the field of corn planting, my country occupies an important position and is a well-deserved planting power. Plant growth stimulants play many key roles in corn growth. It can effectively control the germination and dormancy of seeds, actively promote rooting, significantly enhance the plant's resistance to stress (such as resistance to diseases, drought, salt and cold, etc.), effectively regulate its endogenous hormones, improve the taste of fruits, and enhance the absorption capacity of 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 indicators of fruits, while non-endogenous exogenous active substances are called plant growth stimulants. In the growth process of corn plants, plant growth stimulants, like nutrients such as sunlight, temperature, and water, play a key role in plant growth. By adding plant growth stimulants, the growth of corn plants can be effectively promoted, the development of the roots of corn crops can be significantly promoted, and the biomass of plants can be increased. At present, most of the compounds used in plant growth regulators are artificially synthesized. Therefore, developing a pollution-free plant growth stimulant is critical to protecting the environment, improving the quality of agricultural products and ensuring food safety. Summary of the invention

[0003] In order to solve the above technical problems, the present invention provides the preparation and application of naphthoxybisaminomethyl ester compounds, using 2-naphthoxyacetic acid and N, N-dimethylaminoethanol as raw materials, and obtaining a compound that stimulates plant growth through a one-step synthesis method, and the synthesis method and post-treatment method are simple. The solvent can be recycled to reduce the impact of the solvent on the environment and reduce production costs. The invention has a simple process, is green and environmentally friendly, has a high yield and stable product performance. It provides a new research direction for achieving high-quality green development of ecological agriculture.

[0004] The present invention first provides a naphthoxybisaminomethyl compound, the structural formula of which is:

[0005] The present invention also provides a method for preparing the above-mentioned 2-naphthyloxyacetic acid and N,N-dimethylaminoethanol compound, comprising the following steps: 1) Using 2-naphthyloxyacetic acid and N,N-dimethylaminoethanol as raw materials, toluene as solvent, concentrated sulfuric acid as catalyst, stirring at a certain temperature, and reacting for a certain time; 2) After the reaction is completed, the naphthoxybisaminomethyl ester compound is obtained by vacuum distillation while hot, and the solvent is recovered and reused; Preferably, in step 1), the molar ratio of 2-naphthyloxyacetic acid to N,N-dimethylaminoethanol is 1:1.66.

[0006] More preferably, in step 1), the reaction temperature is 112° C. and the reaction time is 6 hours.

[0007] More preferably, in the step 2), the vacuum distillation temperature is 70° C. and the rotary evaporation time is 1 hour.

[0008] The present invention also provides the application of the naphthoxybisaminomethyl ester compound, which can be used as a plant growth stimulant.

[0009] More preferably the plant of choice is corn.

[0010] Compared with the prior art, the advantages of the present invention are: The naphthoxybisaminomethyl ester compound 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 naphthoxybisaminomethyl ester compound synthesized by the present invention 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

[0011] Figure 1 The reaction equation of naphthoxybisaminomethyl ester prepared in Example 1 is shown in FIG.

[0012] Figure 2 This is a high-resolution mass spectrum of the target product prepared in Example 1 and N,N-dimethylaminoethanol. DETAILED DESCRIPTION

[0013] In order to make the purpose, technical solution and advantages of the present invention clearer, the present invention is further described in detail in conjunction with the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0014] Example 1: Preparation method Weigh 2.5145 g (12.45 mmol) of 2-naphthyloxyacetic acid and 1.5180 g (17.06 mmol) of N, N-dimethylaminoethanol into a 250 mL three-necked flask, then add 90 mL of toluene, drop 0.5 mL of concentrated sulfuric acid as a catalyst, put into a rotor and connect a condenser, react at 112 °C for 6 hours, and after the reaction is completed, distill to obtain 4.368 g of a brown-yellow oily liquid with a yield of 95%.

[0015] Example 2: 1. Experimental method for promoting growth of corn by hydroponics: After sterilizing corn seeds, place them in a culture dish covered with filter paper, wet clean sterile cotton and place them on the filter paper, add 10 mL of sterile water to keep the seeds moist, and then place the culture dish in a constant temperature incubator at 28°C to ensure that the seeds can germinate normally. After the seeds germinate, select corns with the same growth potential and transplant them into a seedling tray. When the first true leaf begins to unfold, weigh the 2-naphthoxybisaminomethyl ester compound and 2-naphthoxyacetic acid prepared in Example 1 to prepare different standard solutions for root irrigation. After 12 days, observe and measure the data such as plant height, root length, plant weight, and root weight.

[0016] 2. Analysis of experimental results: Table 1 Experimental data of corn treated with different solution concentrations

[0017] The results can be seen from Table 1: From the comparison and analysis of the average plant height, average root length, average plant weight, average root fresh weight and root dry weight data with the control, in general, 2-naphthoxyacetic acid and 2-naphthoxybisaminomethyl ester had better effects than the control group, among which the treatment with 1.2ppm of 2-naphthoxybisaminomethyl ester had the best effect. Compared with the data of the control group, after the treatment with 1.37ppm of 2-naphthoxybisaminomethyl ester, the average root fresh weight increased by 56%, and the average root dry weight increased by 109%.

Claims

1. A naphthoxybisaminomethyl ester, characterized in that Its structural formula is: The preparation method of naphthylaminoethyl ester comprises: S1. Use 2-naphthoxyacetic acid and N,N-dimethylaminoethanol as raw materials, toluene as solvent, and concentrated sulfuric acid as catalyst. S2. After the reaction is completed, reduce the pressure and distill while hot, and obtain the naphthoxybisaminomethyl ester compound after concentration.

2. A method for preparing naphthoxybisaminomethyl ester according to claim 1, characterized in that: include: S1. The molar ratio of 2-naphthyloxyacetic acid to N,N-dimethylaminoethanol is 1:1.66, the catalyst is concentrated sulfuric acid 0.5 ml, the reaction temperature is 112 °C, and the reaction time is 6 hours. S2. After the reaction is completed, the vacuum distillation temperature is 70 °C and the time is 1 hour.

3. The use of the naphthoxybisaminomethyl compound according to claim 1, characterized in that: The compound containing naphthoxybisaminomethyl is used as a plant growth stimulant.

4. The use of the naphthoxybisaminomethyl compound according to claim 3, characterized in that: When used as a plant growth stimulant, the plant of choice is corn.

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