A compound containing an oxalate structure, a preparation method and an application

Abstract

The present invention belongs to the field of plant growth stimulants, and particularly relates to a compound containing an oxalate structure, its preparation method and application. In the present invention, oxalic acid and 2-(diethylamino)ethanol are used as raw materials, under the condition that toluene is used as a solvent, the temperature is controlled at 130 °C, and after stirring and reacting for 6 hours, further reduced pressure distillation is carried out to obtain the target product bis(2-(diethylamino)ethyl) oxalate. The said compound has a promoting effect on seed germination. When root irrigation is carried out during the plant growth period, it can promote plant growth and significantly increase the plant biomass. The compound containing an oxalate structure of the present invention has the advantages of high yield, good stability, low product dosage and obvious effect. Therefore, it can be widely used in aspects such as crop growth and increasing production or improving quality and efficiency of agricultural products.

Description

Technical Field

[0001] The present invention belongs to the field of plant growth stimulants, and particularly relates to a preparation method and application of a compound containing oxalate ester. This compound can effectively improve the germination rate of cotton seeds, promote the growth of tomato plants, significantly increase the root length of corn, and ultimately achieve the effect of stimulating crop growth. Background Art

[0002] With the continuous development of modern agriculture, plant growth stimulants are widely used in the process of crop production. They can effectively regulate the generation of nucleic acids, proteins, and enzymes in plants. They play a very important role in different periods of plant growth and development, especially in improving the germination rate of seeds and promoting the healthy growth of plants. Currently, plant growth stimulants have been widely and reasonably used in the plant growth cycle as one of the important methods to improve the stress resistance and yield of modern crops. In recent years, the research on plant growth stimulants has received extensive attention and research. Especially in aspects such as promoting plant growth and stress resistance, improving quality, increasing crop yield, and enhancing planting efficiency, it is a technology with broad application prospects. Therefore, it is very necessary to develop a plant growth stimulant with remarkable effects, green technology, and no pollution to protect the environment, improve the quality of agricultural products, and ensure food safety. This is of great significance for realizing the green and sustainable development of modern agriculture.

[0003] Oxalate ester is oxalic acid, that is, ethanedioic acid. Oxalic acid, namely ethanedioic acid, is one of the simplest organic dibasic acids, with the structural formula HOOCCOOH. It is generally a colorless and transparent crystal, harmful to the human body, which can disrupt the acid-base balance in the human body and affect the development of children. Oxalic acid plays an important role in industry. It can remove rust. Oxalic acid is widespread in nature and often exists in the cell membranes of plants such as barberry, plantain, wood sorrel, and dock in the form of oxalates. Almost all plants contain oxalates, and its safety performance is reliable.

[0004] The present invention aims to provide a new compound containing an oxalate ester structure and its application as a plant growth stimulant. Summary of the Invention

[0005] To solve the above technical problems, the present invention provides a preparation method and application of a compound containing oxalate ester. Oxalic acid and 2-(diethylamino)ethanol are selected as raw materials, and a plant growth stimulant is obtained through a one-step synthesis method. Its synthesis method and post-treatment method are simple, and the solvent can be recycled, thereby avoiding problems such as cumbersome processes and solvent waste. The invention has the characteristics of simple process, environmental protection, high yield of the target product, and remarkable product effects. These characteristics provide new ideas for realizing the high-quality green development of ecological agriculture.

[0006] The present invention first provides a compound containing oxalate ester, and its structural formula is:

[0007]

[0008] The present invention also provides a method for preparing the above-mentioned compound containing oxalate, which comprises the following steps:

[0009] 1) Using oxalic acid and 2-(diethylamino)ethanol as raw materials, using toluene as a solvent, stirring at a certain temperature for a certain period of time;

[0010] 2) After the reaction is completed, distilling under reduced pressure while it is hot to obtain the compound containing oxalate. The solvent can be recycled after recovery;

[0011] Preferably, in the step 1), the molar ratio of oxalic acid to 2-(diethylamino)ethanol is 1:(2 - 3.5).

[0012] More preferably, in the step 1), the reaction temperature is 130 - 135 °C and the reaction time is 5 - 6 hours.

[0013] More preferably, in the step 2), the temperature for distillation under reduced pressure is 100 - 110 °C and the drying time is 1.5 - 2.0 hours.

[0014] The present invention also provides the application of the above-mentioned compound containing oxalate, which can be used as a plant growth stimulant, and the optimal concentration is 30 - 50 mg / L.

[0015] More preferably, the selected plants are cotton, tomato and corn.

[0016] Compared with the prior art, the advantages of the present invention are as follows:

[0017] The compound containing oxalate prepared by the present invention can significantly improve the germination rate of cotton seeds, promote the growth of tomato plants, increase the growth of corn roots, and has a wide range of applicable crops. This compound has the advantages of good stability, low dosage of the target product, low toxicity, prominent action effect and no pollution to the environment, and can be widely used as a plant growth stimulant. Description of the Drawings

[0018] Figure 1 It is the NMR spectrum of the target product prepared in Example 1.

[0019] Figure 2 It is the IR spectrum of the target product prepared in Example 1.

[0020] Figure 3 It is the reaction equation of bis(2-(diethylamino)ethyl) oxalate prepared in Example 1.

[0021] Figure 4Germination effect diagram of cotton seeds of the target product prepared in Example 1.

[0022] Figure 5 Growth promotion effect diagrams of tomatoes and corn of the target product prepared in Example 1. Detailed implementation manners

[0023] To make the objectives, technical solutions and advantages of the present invention clearer, the present invention will be further described in detail below 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.

[0024] Example 1 (I) Preparation of the compound

[0025] Weigh 40 g (444 mmol) of oxalic acid and put it into a 500 ml three-necked flask together with 104 g (888 mmol) of 2-(diethylamino)ethanol. Then add 300 mL of toluene, put in a rotor and connect a condenser, and react at 130 °C for 24 hours. After the reaction is completed, filter to obtain 125 g of white powdery solid, and the yield is 97.66%.

[0026] (II) Structure characterization

[0027] 1 1H NMR: Accurately weigh 50 mg of the sample and add it to a nuclear magnetic tube. Add a small amount of deuterated DMSO reagent to dissolve it, and use a German Bruker 500M nuclear magnetic resonance instrument for testing. 1 1H NMR (500 MHz, DMSO) δ 3.59–3.41 (m, 4H), 2.70–2.64 (m, 12H), 0.99 (t, J J = 7.1 Hz, 12H). (Appendix Figure 2 ) IR(KBr): λmax / cm -1 3379.16 cm -1 (N-H), 2961.01 cm -1 (C-H), 1618.78 cm -1 (C=O), 1070.56 cm -1 (C-O), 772.11 cm -1 (C-C). (Appendix Figure 3 ) Example 2

[0028] Weigh 40 g (444 mmol) of oxalic acid and put it into a 500 mL three-necked flask together with 130 g (1100 mmol) of 2-(diethylamino)ethanol. Then add 300 mL of toluene, put in a magnetic stir bar and connect a condenser. React at 130 °C for 24 hours. After the reaction is completed, filter to obtain 126 g of white powder solid, with a yield of 81.82%. Example 3

[0029] Weigh 40 g (444 mmol) of oxalic acid and put it into a 500 mL three-necked flask together with 156 g (1330 mmol) of 2-(diethylamino)ethanol. Then add 300 mL of toluene, put in a magnetic stir bar and connect a condenser. React at 130 °C for 24 hours. After the reaction is completed, filter to obtain 124 g of white powder solid, with a yield of 68.89%. Example 4

[0030] Weigh 40 g (444 mmol) of oxalic acid and put it into a 500 mL three-necked flask together with 104 g (888 mmol) of 2-(diethylamino)ethanol. Then add 300 mL of toluene, put in a magnetic stir bar and connect a condenser. React at 140 °C for 24 hours. After the reaction is completed, filter to obtain 101 g of white powder solid, with a yield of 78.90%. Example 5

[0031] Weigh 40 g (444 mmol) of oxalic acid and put it into a 500 mL three-necked flask together with 104 g (888 mmol) of 2-(diethylamino)ethanol. Then add 300 mL of toluene, put in a magnetic stir bar and connect a condenser. React at 120 °C for 24 hours. After the reaction is completed, filter to obtain 104 g of white powder solid, with a yield of 81.25%. Example 6

[0032] Treat cotton seeds with 0 (blank control, CK), 20 mg / Kg, 30 mg / Kg, 40 mg / Kg, 50 mg / Kg, and 60 mg / Kg respectively. After wet mixing and air drying the seeds, place them in a petri dish lined with filter paper, add 20 mL of sterile water to keep the seeds moist, and then place the petri dish in a constant temperature incubator at 28 °C to ensure normal germination of the seeds. There are 25 seeds in each treatment, with 4 replicates, and a total of 100 seeds in each treatment. Record the seed germination rate after 7 days.

[0033] Tomato growth promotion experiment method: Weigh the compounds containing oxalate structures prepared in Example 1 respectively to prepare different standard solutions, and use them for root irrigation at 20 mg / Kg, 30 mg / L, 40 mg / L, 50 mg / L, and 60 mg / L respectively in the tomato seedbed and after transplantation. Observe and measure data such as plant height and net weight 7 days later.

[0034] Maize growth promotion experiment method: After disinfecting maize seeds, place them in a petri dish lined with filter paper. Wet a clean sterile cotton ball and place it on the filter paper, add 10 mL of sterile water to keep the seeds moist, and then place the petri dish in a constant temperature incubator at 28°C to ensure normal germination of the seeds. After the seeds germinate, select maize with the same growth vigor and transplant it into a seedling tray. When the first true leaf begins to unfold, use samples with oxalate structures at concentrations of 20 mg / L, 30 mg / L, 40 mg / L, 50 mg / L, and 60 mg / L for root irrigation. Observe data such as plant height and net weight 14 days later.

[0035] Analysis of experimental results:

[0036] Table 1 Germination of cotton seeds treated with different concentrations

[0037]

[0038] Table 2 Plant height and stem diameter of tomatoes treated with different concentrations

[0039]

[0040] Table 3 Plant height and stem diameter of maize treated with different concentrations

[0041]

[0042] It can be seen from Table 1 that all 5 concentrations have effects. Among them, the overall germination rate of 20 mg / Kg is the highest, and the germination rate increases by 7% at the 20 mg / Kg concentration compared with the control. It can be seen from Table 2 that from the analysis of the average plant height, average stem diameter, and total net weight data compared with the control, all 4 concentrations show significant increases, and the effect of 50 mg / L is the best. Compared with the data of the blank control, the plant height at 50 mg / L increases by 24.2%, the stem diameter increases by 17.46%, and the total net weight increases by 32.26%. It can be seen from Table 3 that from the analysis of the average plant height, average stem diameter, average root length, and total net weight data compared with the control. Compared with the data of the blank control, the effect of 30 mg / L is better, the average plant height increases by 6.84%; the average stem diameter increases by 8.68%, the root length increases by 17.88%, and the total net weight increases by 32.01%. Therefore, the compound containing oxalate structure can promote the germination of cotton seeds, increase the plant height of tomatoes, and significantly improve the growth of maize roots. The optimal dosage is 30 - 50 mg / L

[0043] The above-described embodiments merely represent specific implementation manners of the present invention. Their descriptions are relatively specific and detailed, but they should not be construed as limiting the scope of the patent for the present invention. It should be noted that for those of ordinary skill in the art, without departing from the concept of the present invention, several modifications and improvements can still be made, and these all fall within the protection scope of the present invention.

Claims

1. A compound containing an oxalate structure, characterized in that, The structural formula is as follows:

2. The preparation method of the compound containing an oxalate structure according to claim 1, characterized in that, It includes the following steps: 1) Using oxalic acid and 2-(diethylamino)ethanol as raw materials, using toluene as a solvent, stirring at a certain temperature for a certain reaction time; 2) After the reaction is completed, distill under reduced pressure while it is hot. After concentration, the compound containing an oxalate structure described in claim 1 is obtained.

3. The preparation method of the compound containing an oxalate structure according to claim 2, characterized in that, In the said step 1), the molar ratio of oxalic acid to 2-(diethylamino)ethanol is 1:(2 - 3.5).

4. The preparation method of the compound containing an oxalate structure according to claim 2, characterized in that, In the said step 1), the reaction temperature is 130 - 135 °C and the reaction time is 5 - 6 hours.

5. The preparation method of the compound containing an oxalate structure according to claim 2, characterized in that, In the said step 2), the temperature for distillation under reduced pressure is 100 - 110 °C and the time is 1.5 - 2.0 hours.

6. Use of the compound containing an oxalate structure described in claim 1 as a plant growth stimulant.

7. Use of the compound containing an oxalate structure according to claim 6, characterized in that, The application concentration is 30 - 50 mg / L.

8. Use of the compound containing an oxalate structure according to claim 6, characterized in that, When used as a plant growth stimulant, the plants selected are cotton, tomato and corn.

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