Composition containing phenol compound and application thereof

Abstract

The invention relates to a novel plant regulator composition, in particular to a composition containing phenol compounds and application of the composition. The composition containing the phenol compound comprises the phenol compound and a cytokinin substance, and the mass ratio of the phenol compound to the cytokinin substance is (1: 30)-(30: 1); wherein the phenol compound is 4-(2-(methyl-2-(4-methylpent-3-en-1-yl) cyclopent-3-en-1-yl) phenol, the molecular formula is C18H24O, the relative molecular mass is 256.4, and the structural formula is as follows: # imgabs0. According to the invention, the light energy utilization efficiency is obviously improved: the fructus psoraleae seed extract can enhance the light capturing ability of plant chloroplast, and the fructus psoraleae seed extract and cytokinin substances have a synergistic effect, so that the light energy utilization efficiency is improved; the light energy utilization efficiency of plants is remarkably improved, and the photosynthesis of the plants is promoted, so that more organic matters are synthesized, and sufficient energy and material basis are provided for the growth and development of the plants.

Description

Technical Field

[0001] The invention relates to a novel plant regulator composition, in particular to a composition containing phenolic compounds and its application. Background Art

[0002] Cytokinins belong to the category of plant hormones, and their main function is to promote cell division and differentiation. Due to the lack of nutrients, they cannot meet the nutritional needs of plant growth when used alone, which may have an adverse effect on crop yields.

[0003] Psoralea corylifolia seed extract is a plant-derived biopesticide product that has obtained the pesticide registration number PD20190058, the pesticide production license number Pesticide Shengxu (Liao) 0030, and the product standard number Q / SYTX 009-2023. Although Psoralea corylifolia seed extract and its component compounds have potential in preventing and controlling plant diseases and promoting plant growth, the chemical composition of Psoralea corylifolia seeds is extremely complex, with unknown active substances. At the same time, different extraction methods will lead to differences in active substances, and the activity and target of each compound are also different. In addition, the effect of the extract after compounding with other substances cannot be accurately predicted. Summary of the invention

[0004] The purpose of the present invention is to provide a composition containing phenolic compounds and application thereof.

[0005] To achieve the above purpose, the present invention adopts the following technical solution:

[0006] A composition containing phenolic compounds, the composition is a phenolic compound and a cytokinin substance, the mass ratio of the two is 1:30-30:1; wherein the phenolic compound is 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, the molecular formula is C 18 H 24 O, relative molecular mass: 256.4, structural formula is as follows,

[0007]

[0008] The above-mentioned phenolic compounds are obtained by weighing psoralea corylifolia seeds or seed powder, adding water with a mass volume ratio of g:mL of 1:10-20, 20%, 40%, 60% or 80% or 90% ethanol (preferably 60% ethanol with a mass volume ratio of g:mL of 1:10-20), extracting at 25-100°C for 1-4 hours, pouring out the extract, repeating the extraction 2-4 times, combining the extracts, and concentrating the extracts under reduced pressure to a density of 1.0 g / cm 3The crude extract was mixed and suspended with distilled water in a volume ratio of 1:1 to obtain a suspension, and then ethyl acetate of the same volume as the suspension was added thereto and mixed thoroughly. The mixture was allowed to stand and separated into two layers. The ethyl acetate extraction phase was taken, and the operation was repeated 5 times. The ethyl acetate extraction phases were combined and concentrated in vacuum at 45°C to an extract form to obtain the purified psoralea corylifolia seed extract. The purified extract was analyzed by analytical high performance liquid chromatography. The chromatographic column was a Hypersil ODS column (250mm×4.6mm, 5μm), the mobile phase was a volume ratio of 30:70 methanol and 0.1% glacial acetic acid aqueous solution, the flow rate was 1mL / min, the column temperature was 28°C, the injection volume was 10μL, and the maximum absorption wavelength of the psoralea corylifolia seed extract purified by the present patent was determined to be 262nm by full scanning of the sample by analytical liquid chromatography. The purified extract of Psoralea corylifolia seeds was dissolved in methanol at a ratio of 1:10 (g:mL), and further separated and purified by preparative liquid chromatography. The preparation conditions were: chromatographic column (C18-8), mobile phase methanol-water (30:70), injection volume 10mL, flow rate 20mL / min, detection wavelength 262nm, retention time 12.422min. The pure product of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol was obtained, with a content of 97.51%. The substance has the appearance of a light yellow viscous liquid, and the empirical formula is: C 18 H 24 O, relative molecular mass: 256.4, structural formula:

[0009]

[0010] The substance was characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. The spectra are shown in Figure 1 and Figure 2 The liquid chromatogram of content determination is shown in Figure 3 .

[0011] The cytokinin substances are one or more of furfurylaminopurine, benzylaminopurine and hydroxyeneadenine.

[0012] An application of the composition containing phenolic compounds, and an application of the composition in the preparation of a plant growth regulator.

[0013] The dosage form of the regulator is a soluble agent, a wettable powder, a suspension, a soluble powder, a water-dispersible granule, an emulsifiable concentrate, a microcapsule suspension or a microemulsion.

[0014] The preferred dosage form is a soluble solution. Specifically:

[0015] The composition is dissolved in a solvent such as ethanol, glycerol, dimethyl sulfoxide or water, and one or more of T-20, NP-15, NP-7, EL-40, ZSL-6140, S-80, Nongru 500, Nongru 601, Nongru 1600 or T-80 is added to prepare a pesticide soluble solution.

[0016] The composition is used in regulating the growth of fruit trees, vegetables or grain crops, increasing production and income, and improving fruit quality.

[0017] Advantages and effects of the present invention:

[0018] (1) Significantly improve light energy utilization efficiency: Psoralea corylifolia seed extract can enhance the light-capturing ability of plant chloroplasts, and synergize with cytokinin substances to significantly improve the light energy utilization efficiency of plants, promote plant photosynthesis, and thus synthesize more organic matter, providing sufficient energy and material basis for plant growth and development.

[0019] (2) Promote plant growth and development: Psoralea corylifolia seed extract is rich in a variety of nutrients required for plant growth. When mixed with cytokinin substances, it can accelerate cell division, promote plant growth and development, make the plant root system well-developed, the stems thick, and the leaves dark green, and improve the plant's resistance to stress and disease and pests.

[0020] (3) Achieve increased production and harvest: By improving the efficiency of light energy utilization and promoting plant growth and development, the mixed use of Psoralea corylifolia seed extract and cytokinin substances can significantly increase plant yield and quality, achieving the goal of increased production and harvest.

[0021] (4) Reduce fertilizer use and lower costs: Psoralea corylifolia seed extract is rich in various nutrients required for plant growth. When mixed with cytokinin-like substances, it can reduce the use of chemical fertilizers, reduce agricultural production costs, and at the same time reduce the pollution of chemical fertilizers to the environment, thereby achieving sustainable agricultural development. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Figure 1 1H NMR spectrum of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided in an embodiment of the present invention.

[0023] Figure 2 The mass spectrum of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided in an embodiment of the present invention.

[0024] Figure 3 The liquid chromatogram of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided in an embodiment of the present invention. DETAILED DESCRIPTION

[0025] The specific implementation modes of the present invention are further described below in conjunction with examples. It should be noted that the specific implementation modes described herein are only for illustrating and explaining the present invention and are not limited to the present invention.

[0026] Example 1 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol

[0027] Weigh 100g of psoralea corylifolia seeds, add 1000mL of 60% ethanol, extract at 100°C, extract for 4 hours, pour out the extract, repeat the extraction 3 times, combine the extract, and concentrate the extract under reduced pressure to a crude extract with a density of 1.0g / cm3. The crude extract is mixed and suspended with distilled water in a volume ratio of 1:1, and then an equal volume of ethyl acetate is added to the suspension and mixed thoroughly, and the mixture is allowed to stand and separate into two layers, and the ethyl acetate extraction phase is taken, and the operation is repeated 5 times, and the ethyl acetate extraction phase is combined, and vacuum concentrated to an extract at 45°C to obtain a purified psoralea corylifolia seed extract.

[0028] Analyze by analytical high performance liquid chromatography. The chromatographic column is a Hypersil ODS column (250mm×4.6mm, 5μm), the mobile phase is methanol and 0.1% glacial acetic acid aqueous solution in a volume ratio of 30:70, the flow rate is 1mL / min, the column temperature is 28°C, the injection volume is 10μL, and the substance in Example 1 is subjected to a full scan of analytical liquid chromatography to determine that the maximum absorption wavelength of the substance is 262nm. The extract obtained above is dissolved in methanol at a ratio of 1:10 (g / ml), and further separated and purified by preparative liquid chromatography. The preparation conditions are: chromatographic column (C18-8), mobile phase is methanol-water (30:70), injection volume is 10mL, flow rate is 20mL / min, detection wavelength is 262nm, and retention time is 12.422min. The pure product of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol is obtained, with a content of 97.51%. Appearance: light yellow viscous liquid, molecular formula: C18H24O, relative molecular mass: 256.4, structural formula:

[0029]

[0030] The substance was characterized by nuclear magnetic resonance spectroscopy and mass spectrometry. The spectra are shown in Figure 1 and Figure 2 The liquid chromatogram of content determination is shown in Figure 3 .

[0031] Example 2 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.furfurylaminopurine soluble preparation

[0032] Weigh 1.0 g of the phenolic substance obtained in Example 1, add 5 g of furfurylaminopurine, 2 g of ethanol, and 2 g of dimethyl sulfoxide, stir until completely dissolved, then add 3 g of T-80, 0.5 g of Nongru 1600 and 12 g of EL-40, continue stirring until completely mixed, and finally add water to make up to 100 g, stir evenly to obtain 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol. furfurylaminopurine soluble solution preparation.

[0033] Example 3 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.benzylaminopurine soluble preparation

[0034] Weigh 1 g of the phenol substance obtained in Example 1, add 3 g of benzylaminopurine, 2 g of ethanol, and 1 g of dimethyl sulfoxide, stir until completely dissolved, then add 3 g of T-20 and 12 g of ZSL-6140, continue stirring until completely mixed, and finally add water to make up to 100 g, stir evenly to obtain 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.benzylaminopurine soluble solution.

[0035] Example 4 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.hydroxyene adenine soluble preparation

[0036] Weigh 1.2 g of the phenol substance obtained in Example 1, add 3 g of hydroxyene adenine, 2 g of propylene glycol, and 1 g of dimethyl sulfoxide, stir until completely dissolved, then add 3 g of T-80, 2 g of NP-7 and 12 g of EL-40, continue stirring until completely mixed, and finally add water to make up to 100 g, stir evenly to obtain 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.hydroxyene adenine soluble solution.

[0037] Example 5 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol soluble solution

[0038] Weigh 1 g of the phenol substance obtained in Example 1, add 2 g of ethanol, stir until completely dissolved, add 3 g of T-20 and 12 g of ZSL-6140, continue stirring until completely mixed, and finally add water to make up to 100 g, stir evenly to obtain a soluble solution of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.

[0039] Application Example 1 Experiment on the Effect of Tobacco Growth and Yield

[0040] 1. Trial location

[0041] The experiment was carried out in the Xianyang experimental field in Pucheng, Nanping City, Fujian Province. The soil was loose and fertile, with a pH value of 7.3 and medium soil fertility.

[0042] 2. Test Materials

[0043] The tested crop was tobacco, variety: Yunyan 87. The tested agents were the substances of Example 2 and Example 5.

[0044] 3. Experimental Design

[0045] The experiment set up 4 treatments, treatment 1: Example 2 preparation, concentration of 300 mg / L; treatment 2: Example 5 preparation, concentration of 300 mg / L; treatment 3: spraying furan aminopurine powder (commercially available), concentration of 1000 mg / L; treatment 4 (CK): spraying water. Starting from the two-leaf one-heart stage of tobacco, the pesticide was applied once every 30 days for 3 consecutive times.

[0046] 4. Survey items and methods

[0047] When harvesting tobacco leaves from different parts, 10 leaves from the corresponding harvested parts were randomly selected from each plot to measure the leaf length and leaf width, and the average value was calculated. After the tobacco leaves from different parts were harvested and baked, 30 leaves from the corresponding harvested parts were randomly selected from each plot to weigh the total weight of the flue-cured tobacco, and the average value was calculated to measure the weight of a single flue-cured tobacco leaf. Fresh tobacco leaves from all parts of the tobacco leaves were harvested in the whole plot and conventionally baked into flue-cured tobacco. The flue-cured tobacco yield was counted, and the yield was expressed as kg / 667m 2 express.

[0048] The calculation formula is as follows:

[0049] Leaf length (width) adjustment rate = [leaf length (width) of the drug treatment area - leaf length (width) of the water control area] / leaf length (width) of the water control area x 100%;

[0050] Single leaf mass increase rate = (single leaf mass in the drug treatment area - single leaf mass in the water control area) / single leaf mass in the water control area x 100%;

[0051] Yield increase rate = (yield per mu in the treatment area - yield per mu in the water control area) / yield per mu in the water control area x 100%

[0052] When the upper tobacco leaves were harvested, 5 fresh tobacco leaf samples were randomly selected from each plot and placed in an electric forced air drying oven. After baking at a constant temperature of 70°C for 48 hours, they were made into flue-cured tobacco samples. 10 upper fresh tobacco leaf samples were randomly selected from each plot, bagged and marked. The total water-soluble sugar content and protein content of the fresh tobacco leaves were determined by referring to NY / T3030-2016 "Anthrone Colorimetric Method for Determination of Total Water-soluble Sugar Content in Cotton" and GB 5009.5-2016 "National Food Safety Standard Determination of Protein in Food", and the nicotine content in the flue-cured tobacco samples was determined by spectrophotometry.

[0053] 5. Results and Analysis

[0054] Table 1 Effects of different treatments on tobacco leaf length (width)

[0055]

[0056] It can be seen from the above table that each treatment has a certain promoting effect on tobacco leaf length and leaf width, among which treatment 1 has the best promoting effect.

[0057] Table 2 Effects of different treatments on tobacco leaf quality and yield

[0058]

[0059] It can be seen from the above table that each treatment has a certain promoting effect on the quality and yield of tobacco single leaf, among which treatment 1 has the best promoting effect.

[0060] Table 3 Effects of different treatments on tobacco quality

[0061]

[0062]

[0063] It can be seen from the above table that different treatments have no adverse effects on tobacco quality.

[0064] Application Example 2 Experiment on the Effect on Wheat Growth and Yield

[0065] 1. Trial location

[0066] The experimental site is located in Airport Village, Liufenchang, Dashahu Management District, Honghu City, Hubei Province. The experimental site covers an area of ​​28 mu. The soil type is light loam, pH value is 7.0, organic matter content is 1.8%, and the previous crop is soybean.

[0067] 2. Test Materials

[0068] The tested crop was wheat, variety: Huamai 1598. The tested agents were the substances of Example 3 and Example 5.

[0069] 3. Experimental Design

[0070] The experiment set up 4 treatments, treatment 1: Example 3 preparation, concentration of 100 mg / L; treatment 2: Example 5 preparation, concentration of 200 mg / L; treatment 3: spraying benzylaminopurine powder (commercially available), concentration of 1000 mg / L; treatment 4 (CK): spraying water. The pesticide was applied once each at the wheat greening stage, heading stage, and grain filling stage, for a total of 3 times.

[0071] 4. Survey items and methods

[0072] During the wheat harvest period, the wheat plant height, effective ears per unit area, and plot yield are investigated, and samples are taken for quality analysis. At the same time, indoor seed testing samples are taken, and the number of filled grains per wheat ear and the thousand-grain weight are determined after drying.

[0073] Plant height survey: Sampling was conducted at 5 points in each plot, with 4 plants at each point, to measure the wheat plant height.

[0074] Effective ear survey: sampling at 5 points in each plot, 0.25m per point 2 , investigate the effective ears of wheat.

[0075] Yield survey: Each plot is harvested individually, and the yield is measured. The yield statistics are in kg.667m -2 express.

[0076] Indoor seed testing sampling: sampling is conducted at five points in each plot, with 20 plants at each point. The samples are brought back to the laboratory to investigate the number of grains per ear and the thousand-grain weight.

[0077] Wheat quality determination: About 500 g of wheat samples were collected from each treatment plot and sent to a third party for testing of starch, soluble sugar, and protein content.

[0078] 5. Results and Analysis

[0079] Table 4 Effects of different treatments on wheat growth and yield

[0080]

[0081] It can be seen from the above table that Treatment 1 and Treatment 2 can effectively promote wheat growth, increase the number of effective ears, number of grains per ear and thousand-grain weight, etc., and the yield-increasing effect is obvious.

[0082] Table 5 Effects of different treatments on wheat quality

[0083]

[0084] It can be seen from the above table that treatment 1 and treatment 2 can effectively improve wheat quality.

[0085] Application Example 3 Experiment on the Effect of Soybean Growth and Yield

[0086] 1. Trial location

[0087] The experimental site is located in Jixiang Village, Lindian County, Daqing City, Heilongjiang Province. The experimental site covers an area of ​​20 mu. The soil type is light loam, the pH value is 7.9, the organic matter content is 3.1%, and the previous crop is cabbage.

[0088] 2. Test Materials

[0089] The tested crop was soybean, variety: Heihe No. 43. The tested agents were the substances of Example 4 and Example 5.

[0090] 3. Experimental Design

[0091] The experiment set up 5 treatments, treatment 1: Example 4 preparation, concentration of 200 mg / L; treatment 2: Example 5 preparation, concentration of 300 mg / L; treatment 3: spraying hydroxyene adenine powder (commercially available), concentration of 1000 mg / L; treatment 4: Psoralea corylifolia seed extract obtained in Example 1 diluted 3000 times with water to obtain Psoralea corylifolia plant nutrient solution; treatment 5 (CK): spraying water. Spray once at the branching stage and pod-setting stage, for a total of 2 times. Other field management is the same as field production.

[0092] Table 6 Effects of different treatments on soybean growth and yield

[0093]

[0094] As can be seen from the above table, treatment 3 and other treatments can significantly promote soybean growth and increase soybean yield.

Claims

1. A composition containing a phenolic compound, characterized in that: The composition comprises a phenol compound and a cytokinin substance, the mass ratio of the two being 1:30-30:1; wherein the phenol compound is 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, the molecular formula of which is C 18 H 24 O, relative molecular mass: 256.4, structural formula is as follows, 2. The composition containing phenolic compounds according to claim 1, characterized in that: The cytokinin substances are one or more of furfurylaminopurine, benzylaminopurine and hydroxyeneadenine.

3. An application of the composition containing phenolic compounds according to claim 1, characterized in that: The composition is used in preparing a plant growth regulator.

4. The use of the composition containing phenolic compounds according to claim 3, characterized in that: The dosage form of the regulator is a soluble agent, a wettable powder, a suspension, a soluble powder, a water-dispersible granule, an emulsifiable concentrate, a microcapsule suspension or a microemulsion.

5. The use of the composition containing phenolic compounds according to claim 3, characterized in that: The composition is used in regulating the growth of fruit trees, vegetables or grain crops, increasing production and income, and improving fruit quality.

Images