A phenol compound and its application

Abstract

The present invention relates to a novel plant regulator composition, specifically a phenol compound and its application. A phenol compound is 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, with the molecular formula C<subgt;18< / subgt>H<subgt;24< / subgt>O, relative molecular mass: 256.4, and the structural formula is as follows, and the application of the compound in plant regulation. A novel plant regulator composition, the composition is the above-mentioned phenol compound and brassinolide substances; wherein, the mass ratio of the phenol compound to the brassinolide substances is 100:1 - 300:1. The growth promotion effect is obvious. The efficacy of this composition is greatly improved compared with that of the single agent, and the mixture of the two has a synergistic effect on the plant growth regulation. The functions are comprehensive. This composition can not only promote plant cell division, effectively promote the growth of plants, but also balance the accumulation of nutrients for crop growth, increase the thousand-grain weight, improve the yield, and improve the fruit variety.

Description

Technical Field

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

[0002] Brassinosteroid substances are a kind of steroid hormones. Such substances currently on the market mainly include: brassinolide, propionyl brassinolide, 24-epibrassinolide, 28-homobrassinolide, 28-epihomobrassinolide, 14-hydroxybrassinolide, which have stress resistance effects. However, brassinosteroid substances do not contain nutrients and cannot provide the necessary nutrient elements for plants when used alone. When the crop growth environment is good, the effect is not obvious, and improper use will also inhibit crop growth.

[0003] Psoralea seed extract is a botanical biopesticide product of our company. Pesticide registration number: PD20190058, pesticide production license number: Pesticide Production License (Liao) 0030, product standard number: Q / SYTX 009-2023. Related patents involving Psoralea seed extract include: "Psoralen Dihydroflavone with Anti-Plant Fungal Activity", "Use of Psoralenol for Controlling Plant Diseases", "Biopesticide for Controlling Plant Fungal Diseases with Psoralidin", "Mixed Preparation of Psoralen Chalconoid Compounds and Psoralen Dihydroflavone for Controlling Plant Diseases", "A Soluble Liquid Agent of Psoralen Chalconoid and Its Preparation Method and Application", "An Iso-Psoralen Chalconoid Microemulsion and Its Preparation Method", "A Soluble Liquid Agent of Iso-Psoralen Chalconoid and Its Preparation Method", and "A Natural Plant Nutrient Solution and Its Application". The above patents only mention that the corresponding extracts and biological substances such as sugars, proteins, and amino acids have the effects of preventing and controlling plant diseases and promoting plant growth. Although Psoralea seed extract and its component compounds can be used to prevent and control plant diseases and promote plant growth, the chemical composition of Psoralea seeds is complex, involving more than 90 kinds of various compounds in total. Moreover, the active substances obtained by different extraction methods are also different, and different compounds have different activities and action targets. In addition, it is impossible to predict what substances it can be compounded with and what effects can be achieved. Summary of the Invention

[0004] The purpose of the present invention is to provide a phenolic compound and its application.

[0005] To achieve the above purpose, the technical solution adopted by the present invention is as follows:

[0006] A phenolic 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,

[0007]

[0008] Use of the compound as described above, the use of the compound in plant regulation.

[0009] The above-mentioned phenolic compound is obtained as follows: Weigh psoralen seeds or seed powder, add water with a mass-to-volume ratio of g:mL of 1:10 - 20, ethanol at 20%, 40%, 60%, 80% or 90% (preferably 60% ethanol with a mass-to-volume ratio of g:mL of 1:10 - 20), extract at 25 - 100°C for 1 - 4 hours, pour out the extract, repeat the extraction 2 - 4 times, combine the extracts, and concentrate the extract under reduced pressure to a density of 1.0 g / cm 3 of the crude extract. Mix the crude extract with distilled water in a volume ratio of 1:1 to obtain a suspension, then add ethyl acetate with the same volume as 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 psoralen seed extract. Analyze it 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 with 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. By performing a full scan of the sample by analytical liquid chromatography, the maximum absorption wavelength of the purified psoralen seed extract of this patent is determined to be 262 nm. Dissolve the above-mentioned purified psoralen seed extract in methanol according to 1:10 (g:mL), and continue to separate and purify it 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, retention time is 12.422 min. Then obtain the pure product of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol with a content of 97.51%. The appearance of this substance is a light yellow viscous liquid, empirical formula: C 18 H 24 O, relative molecular mass: 256.4, structural formula:

[0010]

[0011] 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 .

[0012] A novel plant regulator composition, which is the phenol compound and brassinolide substance as described above; wherein, the mass ratio of the phenol compound to the brassinolide substance is 100:1 - 300:1.

[0013] The brassinolide substance is one or more of brassinolide, propionyl brassinolide, 24-epibrassinolide, 28-homobrassinolide, 28-epihomobrassinolide, 14-hydroxy brassinolide sterol.

[0014] An application of the composition containing brassinolide substance as described above, which is the application of the composition in preparing a plant growth regulator.

[0015] A plant growth regulator, the regulator takes the composition as an active ingredient; wherein, the active ingredient accounts for 0.0001% - 5% of the mass of the regulator.

[0016] The plant regulator is a soluble concentrate, wettable powder, suspension concentrate, soluble powder, water dispersible granule, emulsifiable concentrate, microcapsule suspension or microemulsion.

[0017] The plant regulator is a soluble concentrate. Specifically:

[0018] Dissolve the composition with solvents such as ethanol, glycerol, dimethyl sulfoxide or water, and add one or more of T-20, NP-15, NP-7, EL-40, ZSL-6140, S-80, agricultural emulsifier 500, agricultural emulsifier 601, agricultural emulsifier 1600 or T-80 to process into a pesticide soluble concentrate.

[0019] An application of the plant growth regulator as described above, which is the application of the plant regulator in regulating the growth of fruit trees, vegetables or food crops, increasing production and income, and improving fruit quality.

[0020] Prepare the preparation into liquid medicines with different concentrations with water and apply them to the surface of crops, which can effectively promote the growth of plants, increase the 1000-grain weight, increase the yield and improve the fruit variety.

[0021] Advantages and effects of the present invention:

[0022] 1. The growth promotion effect is obvious. The drug effect of the composition is greatly improved compared with the single agent, and the mixture of the two has a synergistic effect on the plant growth regulation.

[0023] The composition can not only promote plant cell division, effectively promote the growth of plants, but also balance the accumulation of crop growth nutrients, increase the 1000-grain weight, increase the yield and improve the fruit variety.

[0024] 3. Controllable growth. The composition can intelligently adjust the proportions of nutrients such as plant proteins, fats, and starches according to the different types of nutrients required during different growth periods of crops, and rationally deliver them to the required parts. It can avoid the phenomenon of "insufficient needed and excessive unneeded" caused by the passive stress absorption of plants under exogenous feeding conditions.

[0025] 4. Green and environmentally friendly. The combination of plant-derived pesticides has no toxic or side effects, and natural products are easily degraded, avoiding environmental pollution and harm to natural enemies. Brief Description of the Drawings

[0026] Figure 1 The 1H NMR spectrum of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided by the embodiment of the present invention.

[0027] Figure 2 The mass spectrum of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided by the embodiment of the present invention.

[0028] Figure 3 The liquid chromatogram of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol provided by the embodiment of the present invention. Detailed Embodiments

[0029] The following further illustrates the detailed embodiments of the present invention in conjunction with the embodiments. It should be noted that the detailed embodiments described herein are only for the purpose of illustrating and explaining the present invention and are not limited to the present invention.

[0030] The present invention separates and purifies the new compound 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, which can significantly increase the expression levels of light-harvesting proteins and photosynthesis-related proteins in plant chloroplasts. Further, by mixing it with brassinolide-like substances, it can not only promote plant cell division and growth, but also balance the accumulation of crop growth nutrients, synergistically complement each other at the action targets, and the two mixtures complement each other in function.

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

[0032] 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 and suspend the crude extract with distilled water at a volume ratio of 1:1, then add the same 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.

[0033] 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 with 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, perform an analytical liquid chromatography full scan on the substance in Example 1, and 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, retention time is 12.422 min. That is, 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:

[0034]

[0035] 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 .

[0036] Example 2 Preparation of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol. Brassinolide soluble concentrate

[0037] Weigh 1.0 g of the phenol substance obtained in Example 1, add 0.005 g of brassinolide, add 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 agricultural emulsifier 1600 and 12 g of EL-40, continue to stir until completely mixed, and finally add water to make up to 100 g and stir evenly to obtain 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol. Brassinolide soluble concentrate.

[0038] Example 3 Preparation of the soluble solution of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.propionyl brassinolide

[0039] Weigh 0.5 g of the phenol substance obtained in Example 1, add 0.002 g of propionyl brassinolide, add 2 g of ethanol and 1 g of dimethyl sulfoxide. After stirring until completely dissolved, add 3 g of T-80 and 12 g of EL-40, continue stirring 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.propionyl brassinolide.

[0040] Example 4 Preparation of the soluble solution of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.24-epibrassinolide

[0041] Weigh 0.3 g of the phenol substance obtained in Example 1, add 0.001 g of 24-epibrassinolide, add 2 g of ethanol and 1 g of dimethyl sulfoxide. After stirring until completely dissolved, add 3 g of S-80, 2 g of NP-15 and 12 g of agricultural emulsion 601, continue stirring 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.24-epibrassinolide.

[0042] Example 5 Preparation of the soluble solution of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.28-homobrassinolide

[0043] Weigh 1.2 g of the phenol substance obtained in Example 1, add 0.004 g of 28-homobrassinolide, add 2 g of glycerol and 1 g of dimethyl sulfoxide. After stirring until completely dissolved, 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 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.28-homobrassinolide.

[0044] Example 6 Preparation of the soluble solution of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.28-epihomobrassinolide

[0045] Weigh 0.6 g of the phenol substance obtained in Example 1, add 0.002 g of 28-epibrassinolide, add 2 g of ethanol and 1 g of dimethyl sulfoxide. After stirring until completely dissolved, add 3 g of T-20, 1 g of agricultural emulsifier 500 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 the 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.28-epibrassinolide soluble concentrate.

[0046] Example 7 Preparation of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.14-hydroxybrassinolide soluble concentrate

[0047] Weigh 1.0 g of the phenol substance obtained in Example 1, add 0.01 g of 14-hydroxybrassinolide, add 2 g of ethanol and 1 g of dimethyl sulfoxide. After stirring until completely dissolved, add 3 g of NP-15, 2 g of S-80 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 the 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.14-hydroxybrassinolide soluble concentrate.

[0048] Example 8 Preparation of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol soluble concentrate

[0049] 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 the 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol soluble concentrate.

[0050] Application Example 1 Experiment on the effect of wheat growth and yield

[0051] 1. Test site

[0052] Yanzhuang Village, Suiyang District, Shangqiu City, Henan Province. This plot has been in rotation with wheat and corn all year round. The terrain is flat, the water conservancy facilities are complete, and the soil is fertile.

[0053] 2. Test materials

[0054] The test crop is winter wheat, variety: Zhongmai 175; the test agents are the substances in Example 2 and Example 8.

[0055] 3. Test design

[0056] At the tillering stage, the booting stage and the full heading stage of wheat, the liquid medicine was sprayed by foliar spraying. There were 4 treatments in the experiment. Treatment 1: the preparation of Example 2, the spraying concentration was 50 mg / L; Treatment 2: the preparation of Example 8, the spraying concentration was 200 mg / L; Treatment 3: brassinolide soluble concentrate 2000 mg / L (purchased from the market); Treatment 4 (CK): blank control. Other management measures for the 4 treatments were uniformly carried out according to the requirements of high-yield cultivation, and the wheat dosage for each treatment was 150 kg / hm 2 .

[0057] 4. Investigation items and methods

[0058] 4.1. Determination of wheat morphological characteristics and tiller number

[0059] At the mature stage of wheat, 10 hills were randomly selected from each treatment plot to measure the morphological characteristics of the first internode length at the base of the main stem, the second internode length at the base, the internode length below the ear, the ear length and the plant height. After the five-leaf stage of wheat in the field, 3 points were fixed in each treatment plot for the investigation of the population tiller number.

[0060] 4.2. Determination of yield and its components

[0061] Before the mature harvest of wheat, 1 m 2 of the sample plot was selected from each plot to investigate the ear number, and another 30 plants were taken for indoor seed testing to determine the number of grains per ear. After the grains were air-dried, 1000 grains were counted and weighed. The yield was measured by measuring 4 m 2 in each plot, and after harvesting, it was air-dried naturally and weighed, and converted to mu yield.

[0062] 5. Results and analysis

[0063] Table 1 Effects of the preparations of Example 2 and Example 8 on wheat growth characteristics

[0064]

[0065] From Table 1, compared with the blank control and the single-substance preparation treatment, after treatment with the preparation of Example 2, it can effectively increase the plant height, internode length, ear length and tiller number of the plant, providing favorable material conditions for the increase of yield.

[0066] Table 2 Effects of the preparations of Example 2 and Example 8 on wheat yield and its components

[0067]

[0068] From Table 2, compared with the blank control and the common medicament treatment, after treatment with the preparation of Example 2, the number of grains per ear and 1000-grain weight of wheat can be significantly increased, and the wheat yield can be increased.

[0069] Test on the effects of Application Example 2 on eggplant growth and quality

[0070] 1. Trial Location

[0071] The moist soil in Wuzhuang Village, Economic and Technological Development Zone, Heze City, Shandong Province, where eggplant has never been grown.

[0072] 2. Test Materials

[0073] The test crop was eggplant, and the variety was purple-red long eggplant; the test agents were the preparations of Example 1, Example 3 and Example 8.

[0074] 3. Experimental Design

[0075] The experiment was conducted in a glass greenhouse in November 2023. Potting was performed using a potting method. The test soil was mixed evenly and placed in 24 cm x 18 cm plastic pots, with 2.5 kg per pot. Eggplant seeds were sown using conventional seed soaking and germination acceleration. After the cotyledons expanded, they were planted in plastic pots, with two eggplant seedlings planted in each pot. When the eggplant seedlings had four leaves and one heart, they were thinned out, leaving one eggplant seedling with relatively uniform growth in each pot. The spraying of the chemical began. Five treatments were included: Treatment 1: Preparation of Example 3, concentration 200 mg / L; Treatment 2: Preparation of Example 8, concentration 400 mg / L; Treatment 3: Spraying of a commercially available propionylbrassinolide soluble solution, concentration 1000 mg / L; Treatment 4: Psoralea corylifolia plant nutrient solution prepared by diluting the extract of Psoralea corylifolia seeds obtained in Example 1 3000-fold with water; and Treatment 5 (CK): Spraying of clean water. Treatments were repeated every 10 days for a total of three treatments. When spraying, use a small spray bottle to spray the front and back of the eggplant leaves in a mist form, and spray until liquid droplets just fall.

[0076] 4. Survey items and methods

[0077] Ten days after the last application, 10 eggplant plants were randomly selected and evaluated for plant height, fruit set rate of both inner and outer eggplants, stem diameter, and chlorophyll content. At harvest, 10 eggplant plants were randomly selected and evaluated for fruit traits including number of fruits per plant, fruit weight, fruit length, fruit diameter, fruit shape, and gloss. Plant height was measured with a tape measure, stem diameter with a vernier caliper, and chlorophyll content (SPAD) was determined using a chlorophyll meter (SPAD-502). Each harvest was individually weighed and converted to yield per 667 m2. Dry matter content was determined using the oven-drying method.

[0078] 5. Results and Analysis

[0079] Table 3 Effects of Example 3 and Example 8 on eggplant growth indicators

[0080]

[0081] The results in Table 3 show that the preparation of Example 3 can significantly increase the plant height, diameter, and chlorophyll content of eggplant plants, thereby promoting biomass accumulation and fruit setting rate.

[0082] Table 4 Effects of the formulations in Example 3 and Example 8 on the fruiting of eggplants

[0083]

[0084] Table 4 results show that spraying the formulation in Example 3 can significantly increase the mass and length of single eggplant fruits, improve the fruit shape, make their color and luster bright, increase the yield per mu and the dry matter content, and greatly improve the production efficiency.

[0085] Test on the effect of Application Example 3 on watermelon growth

[0086] 1. Test site

[0087] Conducted in a watermelon greenhouse in Liangzhuang Town, Daiyue District, Tai'an City, Shandong Province.

[0088] 2. Test materials

[0089] The test crop is watermelon, and the variety is Black Beauty; the test agents are the formulations in Example 4 and Example 8.

[0090] 3. Test design

[0091] On the day when the female flowers of watermelon bloom, randomly select watermelon seedlings with basically the same plant size, stem thickness, number of branches, flower quantity and growth vigor for the test. The test has 4 treatments. Treatment 1: the formulation in Example 4, with a concentration of 300 mg / L; Treatment 2: the formulation in Example 8, with a concentration of 500 mg / L; Treatment 3: 24-epibrassinolide soluble solution (purchased on the market), with a concentration of 500 mg / L; Treatment 4 (CK): spraying clear water. Treat once every 10 days, for a total of 3 times. Spray the liquid medicine on the ovary and pedicel of the female flower, and each treatment has 4 replicates.

[0092] 4. Investigation items and methods

[0093] After the last application of the medicine, when the fruits are mature, randomly pick 5 fruits from each replicate, and measure the single fruit weight, pedicel thickness and soluble solid content. The soluble solid content is measured with a WYT - hand-held refractometer.

[0094] After the last application of the medicine, when the watermelon is mature, measure the plant growth indexes and physiological indexes. Among the growth indexes, measure the main vine length, stem thickness at the 5th node, internode length at the 5th node and petiole length of the true leaf at the 5th node of the watermelon plant respectively. Measure the chlorophyll content (SPAD) of the true leaves of each watermelon plant in each plot for the physiological index. Pick watermelons, conduct the determination of watermelon fruit quality and yield, count the fruit setting rate respectively, weigh the single melon weight, calculate the yield and convert it to the unit yield. Use a hand-held refractometer to measure the total soluble solid content in the central part and the part near the rind of the watermelon fruit respectively, use the sodium hydroxide titration method to detect the organic acid content of the fruit, and use the 2,6-dichlorophenol indophenol titration method to measure the vitamin C content in the fruit. Use a saccharimeter to measure the central sugar content.

[0095] 5. Results and Analysis

[0096] Table 5 Effects of the preparations in Example 4 and Example 8 on the growth indexes of watermelon

[0097]

[0098] Table 6 Effects of the preparations in Example 4 and Example 8 on the yield and quality of watermelon

[0099]

[0100]

[0101] Tables 5 and 6 show that the preparation in Example 4 has a good promoting effect on the growth indexes of watermelon plants and the fruit variety products.

[0102] Test on the effect of Application Example 4 on citrus yield

[0103] 1. Test site

[0104] The test was arranged in Meiwan Village, Shuangqiao Town, Danling County, Meishan City. The orchard soil is purple soil, with a pH value of 6.3 and medium soil fertility.

[0105] 2. Test materials

[0106] The crop is citrus, the variety is Robertson navel orange, the tree age is 13 years, and the plant spacing is 2m×3.3m; the test agents are the substances in Example 6 and Example 9.

[0107] 3. Test design

[0108] This test was set with a total of 4 treatments. Treatment 1: the preparation in Example 5, with a concentration of 100mg / L; Treatment 2: the preparation in Example 8, with a concentration of 250mg / L; Treatment 3: 28-homobrassinolide soluble concentrate (purchased from the market), with a concentration of 250mg / L; Treatment 4 (CK): spraying clear water. Each treatment was applied once at the full-bloom stage, young fruit stage and fruit swelling stage of citrus. The application method was whole-plant spraying, focusing on spraying flowers and young fruits, and the spraying amount was 1500L / hm 2 . times.

[0109] 4. Investigation items and methods

[0110] After the citrus fruits mature, randomly pick 3 citrus fruits from each of the five directions (east, south, west, north, and middle) of each tree (15 fruits per plant), with a total of 30 fruits per plot, and measure the fruit diameter and single fruit weight. Then, randomly select 10 of them for quality testing. After sampling and investigation, harvest all the fruits in one go for yield measurement in each plot. Quality determination includes 4 main fruit quality indicators of citrus, namely total sugar, total acid, soluble solids, and vitamin C content. Total sugar is determined by the anthrone colorimetric method. Total acid and soluble solids are measured using a PAL-Acid1 sugar-acid integrated instrument. Vitamin C content is determined by the 2,6-dichloroindophenol method.

[0111] 5. Results and Analysis

[0112] Table 7 Effects of the preparations in Example 5 and Example 8 on the growth of citrus fruits

[0113]

[0114] Table 8 Results of the measurement of citrus quality under the preparations in Example 5 and Example 8

[0115]

[0116] Tables 7 and 8 show that foliar spraying of the preparation in Example 5 during the full bloom stage, young fruit stage, and fruit swelling stage of citrus can increase the fruit diameter, increase the single fruit weight, improve the yield, and greatly improve the fruit quality.

[0117] Test on the effect of Application Example 5 on tomato growth

[0118] 1. Test location

[0119] The test was carried out in the vegetable field of Xiuling Village, Gushan Town, Jin'an District, Fuzhou City. The altitude of the test field is 20m, the soil quality is sandy loam, and the fertility is medium to high.

[0120] 2. Test materials

[0121] The crop is tomato, and the variety is Emperor Red Cherry; the tested pesticides are the preparations in Example 6 and Example 8.

[0122] 3. Test design

[0123] This test was set with a total of 4 treatments. Treatment 1: The preparation in Example 6, with a concentration of 100 mg / L; Treatment 2: The preparation in Example 8, with a concentration of 200 mg / L; Treatment 3: 28-epibrassinolide soluble concentrate (purchased on the market), with a concentration of 200 mg / L; Treatment 4 (CK): Spraying clear water. Apply the pesticides for the first time 7 days before tomato flowering, for the second time during the flowering period, and for the third time 7 days later during the tomato flowering and fruit setting period. The spraying volume is 750 kg / hm 2 . When applying the pesticides, use plastic film as a barrier for isolation to prevent the drift of droplets.

[0124] 4. Investigation Items and Methods

[0125] Fruit setting rate investigation: During the fruit setting period of tomatoes, investigate the fruit setting rate of each plot. When investigating, check 10 tomato plants in each plot. Adopt the parallel line sampling method. Check the total number of flowers of 3 representative inflorescences on each plant, investigate the total number of fruits, and calculate the fruit setting rate.

[0126] Yield investigation: Conduct a yield test after the tomatoes are harvested. The tomatoes are gradually harvested when they are ripe. Record the harvest amount of each plot each time, and convert the amount of tomatoes picked continuously 5 times into the yield per hectare.

[0127] Quality determination: When the tomatoes are harvested for the first time, check 10 plants in each plot, and randomly take two fruits from each plant, that is, 20 tomatoes in each plot. Observe and record their appearance, and determine the titratable acid and vitamin C content of the fruits.

[0128] 5. Results and Analysis

[0129] Table 9 Effects of the preparations in Example 6 and Example 8 on the fruit setting rate, yield and quality of tomatoes

[0130]

[0131] As can be seen from the above table, the preparation in Example 6 can significantly increase the fruit setting rate of tomatoes, increase the yield and improve the fruit quality.

[0132] Test on the influence of Application Example 6 on corn growth

[0133] 1. Test Site

[0134] The test was carried out in the corn field of Liji Township, Shangcheng County, Xinyang City, Henan Province. The previous crop was wheat, and the soil was moderately fertile.

[0135] 2. Test Materials

[0136] Corn, variety is Zhengdan 958; The tested agents are the preparations in Example 7 and Example 8.

[0137] 3. Test Design

[0138] This test was set with a total of 4 treatments. Treatment 1: The preparation in Example 7, with a concentration of 300 mg / L; Treatment 2: The preparation in Example 8, with a concentration of 600 mg / L; Treatment 3: 4-hydroxy brassinolide soluble concentrate (purchased from the market), with a concentration of 600 mg / L; Treatment 4 (CK): Spraying clear water. The first application was carried out at the seedling stage of corn (6-7 leaves), and the second application was carried out at the large bell mouth stage of corn. Use the Dayuan brand 3WBD-16 type knapsack electric sprayer for application, and the aperture of the spray disc is 1.4-1.6 mm. Add 30 kg of water per mu according to the dosage of the medicine, and make it into a solution for spraying.

[0139] 4. Investigation Items and Methods

[0140] Before harvesting corn, the plant height, stem diameter, and ear height of the corn were measured, and the yield was measured at the time of harvesting. The five-point sampling method was adopted. Five points were selected in each plot, and 2 plants were investigated at each point. The plant height, stem diameter, and ear height of 10 corn plants were measured in total, and the leaf color was observed to understand whether there were deformities in the plants. Ten mature fresh cobs were collected, and a hand-held refractometer was used to measure the soluble sugar content. The yield was measured by measuring all the plants in each plot and then converting it into the yield per mu, and the yield increase rate was calculated. The plant height and ear height were measured with a meter stick, and the stem diameter was measured with a vernier caliper.

[0141] 5. Results and Analysis

[0142] Table 10 Effects of the preparations in Example 7 and Example 8 on corn

[0143]

[0144] As can be seen from Table 10, the preparation in Example 7 can promote the growth of corn plants, make them stronger, reduce the ear height, effectively prevent lodging, increase the yield per mu, and increase the soluble sugar content in the seeds.

Claims

1. A phenolic compound, characterized in that: The 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 phenol compound according to claim 1, characterized in that: Use of the phenol compound in regulating the growth of fruit trees, vegetables or food crops, increasing production and income, and improving fruit quality.

3. A plant regulator composition, characterized in that: The composition is the phenol compound and brassinolide substances described in claim 1; wherein, the mass ratio of the phenol compound to the brassinolide substances is 100:1 - 300:1; The brassinolide substances are one or more of brassinolide, propionyl brassinolide, 24-epibrassinolide, 28-homobrassinolide, 28-epihomobrassinolide, 14-hydroxy brassinolide.

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

5. A plant growth regulator, characterized in that: The regulator uses the composition described in claim 3 as the active ingredient; wherein, the active ingredient accounts for 0.0001% - 5% of the mass of the regulator.

6. The plant growth regulator according to claim 5, wherein: The plant regulator is a soluble solution, wettable powder, suspension, soluble powder, water dispersible granule, emulsifiable concentrate, microcapsule suspension or microemulsion.

7. The plant growth regulator according to claim 6, characterized in that: The plant regulator is a soluble solution.

8. Use of the plant growth regulator according to claim 5, characterized in that: Use of the plant regulator in regulating the growth of fruit trees, vegetables or food crops, increasing production and income, and improving fruit quality.

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