A composition of a phenolic compound and naphthaleneacetic acid and its application

Abstract

The present invention relates to a novel plant regulator composition, specifically a composition of a phenolic compound and a naphthylacetic acid substance and its application. A composition of a phenolic compound and a naphthylacetic acid substance, the composition is a phenolic compound and naphthylacetic acid in a mass ratio of 1:40-40:1; 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, #imgabs0# The present invention can promote the root growth of crops and make plants strong by mixing the extract of psoralea corylifolia seeds and naphthylacetic acid, especially by root irrigation, and can resist the damage caused by excessive or high toxicity of the drug and make up for the losses caused thereby. Naphthaleneacetic acid itself has the effect of promoting root development, increasing root branching and the number of root hairs, and the extract of psoralea corylifolia seeds may contain certain components that promote plant growth or enhance stress resistance. The combination of the two can produce a synergistic effect.

Description

Technical Field

[0001] The present invention relates to a novel plant regulator composition, specifically a composition of a phenol compound and naphthaleneacetic acid and its application. Background Art

[0002] Both naphthaleneacetic acid and Psoralea corylifolia seed extract belong to the field of plant growth regulators. As a plant growth hormone, naphthaleneacetic acid has been widely used in agricultural production to promote crop growth and increase yields. However, its nutrient-free property limits its effectiveness when used alone. As a plant-derived biopesticide, Psoralea corylifolia seed extract has the effects of preventing and controlling plant diseases and promoting plant growth. However, the chemical components of Psoralea corylifolia seeds are complex, the active substances obtained by different extraction methods are different, and different compounds have different activities and different action targets. Therefore, how to make full use of these active substances and compound them with what substances to achieve the best effect is the focus of current research. Summary of the Invention

[0003] The object of the present invention is to provide a composition of a phenol compound and naphthaleneacetic acid and its application.

[0004] To achieve the above object, the technical solution adopted by the present invention is:

[0005] A composition of a phenol compound and naphthaleneacetic acid, wherein the composition is a phenol compound and naphthaleneacetic acid with a mass ratio of 1:40 - 40:1; wherein, the phenol compound is 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, with the molecular formula C 18 H 24 O, relative molecular mass: 256.4, and the structural formula is as follows,

[0006]

[0007] The above-mentioned phenol compound is obtained by: weighing Psoralea corylifolia seeds or seed powder, adding water with a mass-to-volume ratio of g:mL of 1:10 - 20, 20%, 40%, 60% or 80% or 90% ethanol (preferably 60% ethanol with a mass-to-volume ratio of g:mL of 1:10 - 20), extracting at 25 - 100 °C for 1 - 4 hours, pouring out the extraction solution, repeating the extraction 2 - 4 times, combining the extraction solutions, and concentrating the extraction solution under reduced pressure to a density of 1.0 g / cm 3The crude extract. The crude extract was mixed and suspended with distilled water at a volume ratio of 1:1 to obtain a suspension, and then ethyl acetate with the same volume as the suspension was added thereto and mixed well. After waiting for the mixture to stand and separate 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 vacuum concentrated to a paste at 45 °C to obtain the purified Psoralea corylifolia seed extract. It was analyzed by analytical high performance liquid chromatography. The chromatographic column was a Hypersil ODS column (250 mm × 4.6 mm, 5 μm), the mobile phase was methanol and 0.1% acetic acid aqueous solution at a volume ratio of 30:70, the flow rate was 1 mL / min, the column temperature was 28 °C, the injection volume was 10 μL. By performing an analytical liquid chromatography full scan on the sample, the maximum absorption wavelength of the purified Psoralea corylifolia seed extract of this patent was determined to be 262 nm. The above purified Psoralea corylifolia seed extract 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 was methanol-water (30:70), injection volume 10 mL, flow rate 20 mL / min, detection wavelength 262 nm, retention time was 12.422 min. 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 appearance of this substance was a light yellow viscous liquid, experimental formula: C 18 H 24 O, relative molecular mass: 256.4, structural formula:

[0008]

[0009] This substance was qualitatively analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry. The spectra are shown in Figure 1 and Figure 2 . The liquid chromatogram for content determination is shown in Figure 3 .

[0010] An application of the composition as described above, the application of the compound in plant regulation.

[0011] The application of the composition in the preparation of a plant growth regulator.

[0012] The regulator uses the composition as the active ingredient; wherein, the active ingredient accounts for 2% - 40% of the mass of the regulator.

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

[0014] Preferably, the 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] Advantages and effects of the present invention:

[0017] (1) The mixed use of psoralea corylifolia seed extract and naphthaleneacetic acid, especially the use of root irrigation, can not only promote the growth of crop roots and strengthen the plants, but also resist the damage caused by excessive or highly toxic pesticides and make up for the losses caused by them. Naphthaleneacetic acid itself has the effect of promoting root development, increasing root branches and the number of root hairs, while psoralea corylifolia seed extract may contain certain ingredients that promote plant growth or enhance stress resistance. The combination of the two can produce a synergistic effect.

[0018] (2) Mixing psoralea corylifolia seed extract with naphthylacetic acid can significantly improve the efficacy and delay the emergence of drug resistance. This may be because the two have different mechanisms of action. When used together, they can act on multiple links of plant growth, thereby enhancing the efficacy. At the same time, due to the different mechanisms of action, mixed use can also reduce the risk of drug resistance caused by the use of a single agent.

[0019] (3) The mixed use of the two may also have the potential to increase crop yield and quality and enhance crop resistance (such as drought resistance, cold resistance, disease resistance, etc.). These advantages help improve the overall growth of crops and bring greater economic benefits to agricultural production. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] 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.

[0021] 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.

[0022] 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

[0023] 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.

[0024] Example 1 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol

[0025] Weigh 100 g of Psoralea corylifolia seeds, add 1000 mL of 60% ethanol, extract at 100 °C for 4 hours, pour out the extract, repeat the extraction 3 times, combine the extracts, and concentrate the extract under reduced pressure to a crude extract with a density of 1.0 g / cm3. Mix the crude extract with distilled water in a volume ratio of 1:1 to form a suspension, then add an equal volume of ethyl acetate to the suspension and mix well. Wait for the mixture to stand and separate into two layers. Take the ethyl acetate extraction phase, repeat the operation 5 times, combine the ethyl acetate extraction phases, and concentrate under vacuum at 45 °C to an extract paste to obtain the purified Psoralea corylifolia seed extract.

[0026] Analyze by analytical high performance liquid chromatography. The chromatographic column is a Hypersil ODS column (250 mm × 4.6 mm, 5 μm), the mobile phase is methanol and 0.1% acetic acid aqueous solution in a volume ratio of 30:70, the flow rate is 1 mL / min, the column temperature is 28 °C, the injection volume is 10 μL, and perform an analytical liquid chromatography full scan on the substance in Example 1 to determine that the maximum absorption wavelength of the substance is 262 nm. Dissolve the above-obtained extract in methanol at a ratio of 1:10 (g / ml), and continue to separate and purify by preparative liquid chromatography. The preparation conditions are: chromatographic column (C18-8), mobile phase is methanol-water (30:70), injection volume 10 mL, flow rate 20 mL / min, detection wavelength 262 nm, and retention time is 12.422 min. That is, a 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:

[0027]

[0028] This substance is qualitatively analyzed by nuclear magnetic resonance spectroscopy and mass spectrometry. The spectra are shown in Figure 1 and Figure 2 . The liquid chromatogram for content determination is shown in Figure 3 .

[0029] Example 2 Preparation of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol·naphthaleneacetic acid soluble concentrate

[0030] Weigh 1.0 g of the phenol substances obtained in Example 1, add 5 g of naphthalene acetic acid, 5 g of ethanol, and 5 g of dimethyl sulfoxide. After stirring until completely dissolved, add 3 g of T-80, 0.5 g of agricultural emulsifier 1600, and 12 g of EL-40. Continue to stir until completely mixed. Finally, add water to make up to 100 g, and stir evenly to obtain the soluble solution of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol. naphthalene acetic acid soluble concentrate preparation.

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

[0032] Weigh 1 g of the phenol substances 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 to stir until completely mixed, and finally add water to make up to 100 g, and stir evenly to obtain the soluble solution of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.

[0033] Application Example 1 Experiment on the effect of 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol soluble concentrate on rice growth and yield

[0034] 1. Test site

[0035] The test was arranged in the rice fields of Yiquan Town, Donggang City, Dandong City, Liaoning Province, with a test area of 4 mu. The soil is thin-layer acidic rock brown loam soil, the pH value of the test soil is 6.0, and the organic matter content is 0.62%.

[0036] 2. Test materials

[0037] The tested crop is rice, variety: Liaojing 294. The tested agents are the substances of Example 2 and Example 3.

[0038] 3. Test design

[0039] The test was set with 5 treatments. Treatment 1: The preparation of Example 2, with a concentration of 200 mg / L; Treatment 2: The preparation of Example 3, with a concentration of 400 mg / L; Treatment 3: Spraying naphthalene acetic acid powder (purchased from the market), with a concentration of 1000 mg / L; Treatment 4: The psoralen plant nutrient solution obtained by diluting the psoralen seed extract obtained in Example 1 by 3000 times with water; Treatment 5 (CK): Spraying clear water. Spraying was carried out once at the 2-leaf 1-heart stage of rice seedlings, once at the 5-leaf stage, and once at the heading stage, for a total of 3 sprays.

[0040] 4. Investigation items and methods

[0041] Measurement of rice seedling stage traits. At the 3-leaf 1-heart stage of rice, randomly select 10 rice plants and measure the root length, root fresh weight, root dry weight, above-ground fresh weight, and above-ground dry weight of each group.

[0042] After the rice matures, investigate the plant height, panicle length, number of grains per panicle, and seed setting rate. After drying the fresh grains and removing impurities, calculate the 1000-grain weight and yield. Determine the starch content of the rice with reference to GB / T 15683-2008 Determination of Amylose Content in Rice

[0043] 5. Results and Analysis

[0044] Table 1 Effects of Different Treatments on Seedling Traits of Rice

[0045]

[0046] As can be seen from the above table, the above different treatments all have a certain promoting effect on the growth of rice seedlings, among which Treatment 1 has the best effect.

[0047] Table 2 Effects of Different Treatments on Yield and Quality of Rice

[0048]

[0049] As can be seen from the above table, Treatment 1 can significantly increase the yield of rice and improve the quality.

Claims

1. A composition of a phenolic compound and naphthaleneacetic acid, characterized in that: The composition is a phenol compound and naphthaleneacetic acid combined in a mass ratio of 1:40 to 40:1; among them, the phenol compound is 4-(2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, with the molecular formula C 18 H 24 O, relative molecular mass: 256.4, and the structural formula is as follows, 2. Use of the composition according to claim 1, characterized in that: Use of the compound in plant regulation.

3. Use of the composition according to claim 2, characterized in that: Use of the composition in the preparation of a plant growth regulator.

4. Use of the composition according to claim 3, characterized in that: The regulator uses the composition as an active ingredient; wherein, the active ingredient accounts for 2% - 40% of the mass of the regulator.

5. Use of the composition according to claim 4, characterized in that: The dosage form of the regulator is a solution, wettable powder, suspension, soluble powder, water dispersible granule, emulsifiable concentrate, microcapsule suspension or microemulsion.

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