Composition of phenol compound and naphthylacetic acid substance and application thereof

Abstract

The invention relates to a novel plant regulator composition, in particular to a phenol compound and naphthylacetic acid composition and application thereof. The invention relates to a composition of a phenol compound and a naphthylacetic acid substance. The composition is prepared from the phenol compound and the naphthylacetic acid in 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, the molecular formula is C18H24O, the relative molecular mass is 256.4, and the structural formula is as follows: # imgabs0. Through mixing of the fructus psoraleae seed extract and naphthylacetic acid, especially root irrigation, the pesticide composition can promote root growth of crops, enables plants to be robust, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth of the crops, can promote root growth and phytotoxicity caused by excessive medicament or high toxicity can be resisted, so that the loss caused by the phytotoxicity can be made up. Naphthylacetic acid has the effects of promoting root development and increasing the number of root branches and root hair, the fructus psoraleae seed extract possibly contains some components for promoting plant growth or enhancing stress resistance, and the naphthylacetic acid and the fructus psoraleae seed extract are combined for use, so that a synergistic effect can be generated.

Description

Technical Field

[0001] The invention relates to a novel plant regulator composition, in particular to a composition of a phenol compound and naphthylacetic acid and application thereof. Background Art

[0002] Both naphthylacetic acid and psoralea corylifolia seed extract belong to the field of plant growth regulators. As a plant growth hormone, naphthylacetic acid has been widely used in agricultural production to promote crop growth and increase yield. However, its nutrient-free characteristics limit its effect 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 composition of psoralea corylifolia seeds is complex, and the active substances obtained by different extraction methods are different, and different compounds have different activities and different targets. Therefore, how to make full use of these active substances and what substances to compound with them to achieve the best effect is the focus of current research. Summary of the invention

[0003] The purpose of the present invention is to provide a composition of a phenol compound and naphthylacetic acid and application thereof.

[0004] To achieve the above purpose, the present invention adopts the following technical solution:

[0005] A composition of a phenol compound and naphthylacetic acid, wherein the composition is a phenol compound and naphthylacetic acid in 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, and the molecular formula is C 18 H 24 O, relative molecular mass: 256.4, structural formula is as follows,

[0006]

[0007] 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:

[0008]

[0009] The substance was characterized by NMR and mass spectrometry. Figure 1 and Figure 2 The liquid chromatogram of content determination is shown in Figure 3 .

[0010] An application of the composition, and an application of the compound in plant regulation.

[0011] The composition is used in preparing a plant growth regulator.

[0012] The regulator has a composition as an 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 agent, a wettable powder, a suspension, a soluble powder, a water-dispersible granule, an emulsifiable concentrate, a microcapsule suspension or a microemulsion.

[0014] Preferably, the dosage form is a soluble liquid. 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 high toxicity of the pesticide and make up for the losses caused by it. 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 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.

[0026] 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:

[0027]

[0028] The substance was characterized by NMR and mass spectrometry. Figure 1 and Figure 2 The liquid chromatogram of 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.naphthyl acetic acid soluble preparation

[0030] Weigh 1.0 g of the phenol substance obtained in Example 1, add 5 g of naphthylacetic acid, 5 g of ethanol, and 5 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.naphthylacetic acid soluble solution preparation.

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

[0032] 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.

[0033] Application Example 1 Experiment on the effect on rice growth and yield

[0034] 1. Trial location

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

[0036] 2. Test Materials

[0037] The tested crop was rice, and the variety was Liaojing 294. The tested agents were the substances in Example 2 and Example 3.

[0038] 3. Experimental Design

[0039] The experiment set up 5 treatments, treatment 1: Example 2 preparation, concentration of 200 mg / L; treatment 2: Example 3 preparation, concentration of 400 mg / L; treatment 3: spraying naphthaleneacetic acid powder (commercially available), concentration of 1000 mg / L; treatment 4: psoralea corylifolia plant nutrient solution obtained by diluting 3000 times with water from psoralea corylifolia seed extract obtained in Example 1; treatment 5 (CK): spraying with clean water. Spray once at the 2-leaf 1-heart stage of rice seedlings, spray once at the 5-leaf stage, and spray once at the heading stage, for a total of 3 applications.

[0040] 4. Survey items and methods

[0041] Determination of rice seedling traits: At the rice 3-leaf 1-heart stage, 10 rice plants were randomly selected to measure the root length, root fresh weight, root dry weight, aboveground fresh weight, and aboveground dry weight of each group.

[0042] When the rice is mature, the plant height, ear length, number of grains per ear, and fruit setting rate are investigated. After the fresh rice is dried and impurities are removed, the thousand-grain weight and yield are calculated. The starch content of rice is determined in accordance with GB / T 15683-2008 "Determination of Amylose Content in Rice".

[0043] 5. Results and Analysis

[0044] Table 1 Effects of different treatments on rice seedling characteristics

[0045]

[0046] It can be seen from the above table that 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 rice yield and quality

[0048]

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

Claims

1. A composition of a phenolic compound and naphthylacetic acid, characterized in that: The composition is a phenol compound and naphthylacetic acid in 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, and the molecular formula is C 18 H 24 O, relative molecular mass: 256.4, structural formula is as follows, 2. An application of the composition according to claim 1, characterized in that: The compounds are used in plant regulation.

3. The use of the composition according to claim 2, characterized in that: The composition is used in preparing a plant growth regulator.

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

5. The use of the composition according to claim 4, 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.

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