A novel indole-based plant growth regulator, its preparation method, and its application.

Abstract

This invention belongs to the field of vegetation restoration technology, and relates to a novel plant growth regulator, specifically a novel plant growth regulator containing an indole structure, its preparation method, and its applications. The plant growth regulator provided by this invention is an indole compound synthesized from o-phenylenediamine and indole-3-carboxaldehyde. By applying regulator solutions of different concentrations, it can promote or inhibit crop growth under different concentration conditions. Furthermore, due to its structural characteristics, IYAA can form a complex with copper, promoting plant growth under copper stress. The regulator preparation method provided by this invention is simple, has significant effects, and has broad application prospects.

Description

Technical Field

[0001] This invention belongs to the field of vegetation restoration technology and relates to a novel plant growth regulator, specifically a novel plant growth regulator containing an indole structure, its preparation method, and its application. Background Technology

[0002] Plant growth regulators are exogenous active substances synthesized, extracted, or fermented artificially. They possess physiological activities similar to endogenous plant hormones, or can influence the synthesis, transport, metabolism, and physiological functions of endogenous plant hormones. Plant growth regulators promote seed germination, rooting, and flowering; enhance plant resistance to cold, drought, salinity, and pests and diseases; and improve crop yield and quality. They are widely used in agricultural production due to their advantages of low cost, small dosage, and significant effects.

[0003] Plant growth regulators are a major industry attracting worldwide attention and development, and represent a key focus for future agriculture. The scientific use of plant growth regulators can reduce the use of pesticides and fertilizers, thereby mitigating environmental pollution. This not only addresses food security to some extent and meets the growing demand for high-quality agricultural products, but also alleviates increasingly severe environmental problems. The development of novel plant growth regulators has become a research hotspot. Summary of the Invention

[0004] To address the problems existing in the prior art, the present invention aims to provide, for the first time, a novel plant growth regulator IYAA containing an indole structure. The plant growth regulator provided by the present invention can promote wheat growth, and its operation method is simple, its effect is good, and it has broad application prospects.

[0005] Another objective of this invention is to provide a method for preparing the novel plant growth regulator IYAA.

[0006] This invention also provides the application of the aforementioned novel plant growth regulator IYAA.

[0007] To achieve the above-mentioned objectives, the present invention provides the following technical solution:

[0008] This invention provides a novel plant growth regulator having the structure shown in Formula I:

[0009]

[0010] Formula I.

[0011] The present invention also provides a method for preparing the above-mentioned novel plant growth regulator, comprising the following steps: mixing o-phenylenediamine and indole-3-carboxaldehyde with an organic solvent and carrying out an esterification reaction to obtain a novel plant growth regulator having the structure shown in Formula I.

[0012] In some embodiments, the molar ratio of o-phenylenediamine to N-acetic acid-3-indolecarboxaldehyde is 1:1, and the solvent used is anhydrous ethanol.

[0013] In some embodiments, the esterification reaction is carried out under nitrogen protection and reflux under heating conditions.

[0014] In some embodiments, the heating temperature for the esterification reaction is 70 °C, and the reaction time is 12 h.

[0015] In some embodiments, the reaction solution generated by the esterification reaction is cooled to room temperature, evaporated to dryness, then an organic solvent (ethanol) is added for recrystallization upon cooling, and the product is obtained by filtration and purification.

[0016] The specific purification process described above is as follows: add an organic solvent (ethanol) for recrystallization: first cool until a small amount of solid precipitates, then sonicate to precipitate a large amount of solid, filter to obtain a light yellow powder, repeat three times to purify the product.

[0017] This invention also provides the application of the above-mentioned novel plant growth regulator in regulating wheat growth.

[0018] The beneficial effects of this invention are as follows:

[0019] (1) The present invention provides a novel plant growth regulator having the structure shown in Formula I. The plant growth regulator (IYAA) provided by the present invention is a novel plant growth regulator synthesized based on indole compounds. This compound can affect the growth of wheat seedlings by influencing the germination rate and root length of wheat seeds. In particular, it can achieve the same growth-promoting effect as commercial auxins while reducing costs.

[0020] (2) The plant growth regulator provided by the present invention can complex with copper ions due to its own structural characteristics, which can alleviate the stress of copper on wheat to a certain extent.

[0021] (3) The preparation process of the plant growth regulator provided by the present invention is simple and highly controllable. Attached Figure Description

[0022] Figure 1 This is the high-resolution mass spectrum of compound IYAA;

[0023] Figure 2 The image shows the nuclear magnetic resonance (NMR) spectrum of compound IYAA.

[0024] Figure 3 The graph shows the water solubility test results for compound IYAA.

[0025] Figure 4 The graph shows the effect of compound IYAA on the germination rate of wheat seeds.

[0026] Figure 5 Figure showing the effect of compound IYAA on the root and stem length of wheat seedlings under hydroponics;

[0027] Figure 6 Figure 1 shows the effect of compound IYAA on root growth indicators of wheat seedlings grown in soil.

[0028] Figure 7 The figure shows the effect of compound IYAA on the root and stem length of wheat seedlings under copper stress. Detailed Implementation

[0029] This invention provides a method for preparing the plant growth regulator described above, comprising the following steps:

[0030] o-Phenylenediamine and indole-3-carboxaldehyde were dissolved in ethanol and refluxed under nitrogen for 12 hours. The reaction solution was then cooled to room temperature, and the liquid was evaporated to dryness to obtain a crude product. The crude product was recrystallized three times with ethanol, and dried to obtain a pale yellow powder. After drying, a novel plant growth regulator with the structure shown in Formula I was obtained.

[0031] Unless otherwise specified, all raw materials used in this invention are commercially available products well known to those skilled in the art.

[0032] In this invention, the molar ratio of o-phenylenediamine to indole-3-carboxaldehyde is 1:1, and ethanol is selected as the organic solvent.

[0033] The corresponding reactions are shown below.

[0034]

[0035] 1 H NMR (500 MHz ， DMSO) δ 11.73 (s ， 1H) ， 8.75 (s ， 1H) ， 8.41 (d ， J = 7.5 Hz ， 1H) ， 7.99 (s ， 1H) ， 7.49 (d ， J = 7.9 Hz ， 1H) ， 7.28 – 7.16 (m， 2H) ， 7.02 (d ， J = 7.1 Hz ， 1H) ， 6.92 (dd ， J = 10.9 ， 4.1 Hz ， 1H) ， 6.79 – 6.64 (m ， 1H) ， 6.59 (t ， J = 7.5 Hz ， 1H) ， 5.01 (s ， 2H). 13 C NMR (126 MHz ， DMSO) δ 153.17 ， 143.28 ， 138.32 ， 137.66 ， 133.57 ， 126.29 ， 125.24 ， 123.24 ， 122.32 ， 121.40 ， 117.05 ， 116.93 ， 115.95 ， 114.73 ， 112.45. HRMS (m / z): [M + H] + calcd for C 15 H 13 N3: 236.1182 ， found ， 236.1179.

[0036] In this invention, the molar ratio of o-phenylenediamine to indole-3-carboxaldehyde is 1:1, and ethanol is chosen as the organic solvent. o-phenylenediamine and indole-3-carboxaldehyde are dissolved in ethanol, refluxed under nitrogen protection for 12 hours, and the reaction temperature is 70°C. The reaction solution is cooled to room temperature, and the solution is evaporated to dryness to obtain a crude product. The crude product is recrystallized three times with ethanol. First, it is cooled until a small amount of solid precipitates, then ultrasonically precipitates a large amount of solid. The product is filtered to obtain a pale yellow powder. This process is repeated three times to purify the product, and after drying, a pale yellow powder is obtained.

[0037] This invention provides a method for preparing the novel plant growth regulator described in the above-mentioned technical solution. In this invention, the novel plant growth regulator is applied to wheat growth; for example, the novel plant growth regulator can act on different organs of wheat and affect wheat growth.

[0038] The technical solutions of this invention will be clearly and completely described below with reference to the embodiments thereof. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of this invention without creative effort are within the scope of protection of this invention.

[0039] Example 1

[0040] o-Phenylenediamine (1080 mg, 10 mmol) and indole-3-carboxaldehyde (1450 mg, 10 mmol) were dissolved in 90 mL of ethanol. The mixture was refluxed at 70 °C for 12 hours under nitrogen protection. After cooling the reaction solution to room temperature, the liquid was evaporated to dryness and recrystallized three times with 10 mL of ethanol. After drying, 900 mg of a pale yellow powder was obtained (yield: 32.4%).

[0041] Figure 1 This is the high-resolution mass spectrum of compound IYAA. Figure 2 This is the nuclear magnetic resonance (NMR) spectrum of IYAA. (Source: [Insert Source Name here]) Figure 1 and Figure 2 It can be seen that the target product prepared in this embodiment is compound IYAA.

[0042] Example 1

[0043] The water solubility of compound IYAA prepared in Example 1 was determined as follows:

[0044] Compound IYAA was dissolved in pure water to obtain a concentration of 10. -3 M's IYAA stock solution; diluted to a concentration of 10 -4 10 -5 10 -7 10 -9 10 -11 10 -13 M plant growth regulator stock solution.

[0045] Figure 3 The graph shows the water solubility test results for compound IYAA. Figure 3 It can be seen that the compound IYAA has good water solubility, and there are no large insoluble particles or precipitates.

[0046] Example 2

[0047] The effect of compound IYAA prepared in Example 1 on the germination rate of wheat seeds was analyzed in the following experiments:

[0048] Compound IYAA was dissolved in pure water to obtain a concentration of 10. -3 M's IYAA stock solution, diluted to a concentration of 10 -4 10 -5 10 -7 10 -9 10 -11 10 -13 Prepare a stock solution of plant growth regulator M for later use; similarly, prepare and dilute a solution to a concentration of 10. -4 10 -5 10 -7 10 -9 10 -11 10 -13 M's commercial auxin IAA stock solution is ready for use;

[0049] Wheat seeds were disinfected with sodium hypochlorite solution (5-10 min). The sodium hypochlorite solution was then removed, and water was added to cover the seeds. The seeds were left to stand for 30-60 min, the water was drained, and the seeds were spread on clean resealable bags and placed in a ventilated area to dry. Uniformly sized seeds were randomly selected and placed into glass petri dishes lined with filter paper. Finally, diluted IYAA stock solutions of different concentrations were added, and the dishes were labeled. Three stock solution treatments (IYAA, IAA, and CK) were set up, with three replicates for each concentration. The petri dishes were hydroponically cultured at 25 ℃, and an equal amount of stock solution was added every 24 hours.

[0050] Figure 4 This is a comparison graph showing the effects of different concentrations of IYAA and IAA on wheat seed germination rate. Compared with the commercially available auxin IAA, compound IYAA showed a better promoting effect on wheat seed germination rate, especially at a concentration of 10%. -7 M and 10 -9 M time.

[0051] Example 3

[0052] The effect of compound IYAA prepared in Example 1 on the root and stem length of wheatgrass seeds under hydroponics was analyzed in the following experiment:

[0053] Compound IYAA and auxin IAA were dissolved in pure water to prepare and dilute to a concentration of 10. -4 10 -5 10 -7 10 -9 10 -11 10 -13M's IYAA compound and the same concentration of commercial auxin IAA are prepared for use.

[0054] Three stock solution treatment methods were set up: IYAA, IAA, and CK. Three replicates were set up for each concentration. The petri dishes were placed in a room temperature environment of 25°C for hydroponics. An equal amount of stock solution was added every 24 hours. The culture was carried out for 7-14 days, and the root and stem length at each concentration was recorded.

[0055] Figure 5 This is a comparison graph showing the effects of compounds IYAA and IAA at different concentrations on wheat root and stem length. As can be seen from the graph, compared with the commercially available auxin IAA treatment group, compound IYAA showed a better promoting effect on the root and stem length of wheat seedlings, especially at low and medium concentrations (10). -7 -10 -9 M).

[0056] Example 4

[0057] The effects of compound IYAA on the root and stem length of wheat seedlings grown in soil were analyzed in the following experiment.

[0058] Compound IYAA and auxin IAA were dissolved in pure water to prepare and dilute to a concentration of 10. -4 10 -5 10 -7 10 -9 10 -11 10 -13 M's IYAA compound and commercial auxin IAA are ready for use;

[0059] At room temperature, seeds were soaked for 12 hours in 10 mL of IYAA and IAA stock solutions of corresponding concentrations, respectively, with a control (CK) of water. After soaking, 52 flowerpots with a diameter of 15 cm were prepared. Fifty seeds were randomly selected from each petri dish and sown into the flowerpots containing an appropriate amount of soil, evenly distributed, and covered with 1 cm of moistened soil. This process was repeated four times. A fixed amount of solution (5 mL) was added every two days using a spray bottle. Germination rate was recorded starting the day after sowing and continued for 5 days. Plant height was measured 5 days after sowing, with 20 plants measured for each concentration, and then measured every 3 days for 3 weeks. After 3 weeks of continuous cultivation, root length, stem length, fresh weight, dry weight, and chlorophyll content were measured.

[0060] Figure 6This image shows the effects of IYAA and IAA at different concentrations, along with comparisons of various indicators. In the same photograph, the top image shows the effects of different concentrations of IAA (a commercial plant growth regulator) and the control group (CK) on wheat growth, while the bottom image shows the effects of different concentrations of IYAA (a novel plant growth regulator) and the control group (CK) on wheat growth. From left to right, these represent the control group (CK), 10... -4 10 -5 10 -7 10 -9 10 -11 10 -13 Group M. Plant height, root length, chlorophyll content, and biomass were recorded for each treatment group. The bar chart on the right shows that at 10... -7 At time M, IYAA showed the most significant growth-promoting effect on wheat, and this effect was observed at 10 -7 M-type IYAA also showed significant growth-promoting effects on other indicators.

[0061] Example 5

[0062] The effects of compound IYAA on the root and stem length of wheat seedlings under heavy metal stress were analyzed in the following experiment.

[0063] Compound IYAA was dissolved in pure water to prepare and dilute to a concentration of 10. -4 10 -5 10 -7 10 -9 10 -11 10 -13 M's IYAA compound was prepared in advance; and 40 and 80 mg / L Cu was prepared with copper sulfate pentahydrate. 2+ Solution.

[0064] Set IYAA, IYAA+Cu 2+ Cu 2+ Four stock solution treatment methods (CK) were used, with three replicates for each concentration. The petri dishes were placed in a room temperature environment of 25 ℃ for hydroponics. An equal amount of solution was added every 24 hours. The culture was carried out for 7-14 days, and the root and stem length at each concentration was recorded.

[0065] Figure 7 This image shows the effects of different concentrations of IYAA on wheat growth under copper stress, along with a comparative chart of root and stem length data. In the images, the first row represents the treatment group without copper stress, while the second and third rows show the treatment groups with higher concentrations of Cu. 2+ The concentrations were 40 mg / L and 80 mg / L, respectively. In each row, from left to right, the concentrations of IYAA were 0 (CK group) and 10 mg / L. -4 10 -5 10 -7 10 -910 -11 10 -13 M. Both the physical images and the statistical data on root and stem length show that, compared with the treatment group without copper stress, high concentrations of IYAA did not inhibit the growth of wheat under copper stress; on the contrary, their growth-promoting effect was comparable to that of lower concentrations. This demonstrates that IYAA and Cu... 2+ Something happened that reduced the Cu in the petri dish. 2+ The concentration of [something] thus promotes wheat growth.

[0066] As can be seen from the above test examples, the novel plant growth regulator provided by this invention can affect the root and stem length of wheat by influencing the speed of seed germination, and shows differences from the commercially available auxin IAA; the operation method is simple and has broad application prospects.

[0067] The above description is only a preferred embodiment of the present invention. It should be noted that for those skilled in the art, several improvements and modifications can be made without departing from the principle of the present invention, and these improvements and modifications should also be considered within the scope of protection of the present invention.

Claims

1. The application of a plant growth regulator in regulating wheat growth, characterized in that, The plant growth regulator has the structure shown in Formula I: Formula I.

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