Phenol compound and application thereof

Abstract

The invention relates to a novel plant regulator composition, in particular to a phenol compound and application thereof. The phenol compound is 4-(2-methyl-2-(4-methylpent-3-en-1-yl) cyclopent-3-en-1-yl) phenol, the molecular formula of the phenol compound is C18H24O, the relative molecular mass of the phenol compound is 256.4, the structural formula of the phenol compound is as follows: # imgabs0, and the application of the phenol compound in plant regulation is provided. A novel plant regulator composition is prepared from the phenol compound and a brassinolide substance, wherein the composition is a mixture of the phenol compound and the brassinolide substance; wherein the mass ratio of the phenol compound to the brassinolide substance is (100: 1)-(300: 1). The growth promoting effect is obvious. The pesticide effect of the composition is greatly improved compared with that of a single agent, and the mixture of the two agents has a synergistic effect on plant growth regulation. The functions are comprehensive. The composition not only can promote plant cell division and effectively promote plant growth, but also can balance accumulation of crop growth nutrient substances, increase thousand seed weight, increase yield and improve fruit varieties.

Description

Technical Field

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

[0002] Brassinolide is a steroid hormone. Currently, the main substances on the market include: brassinolide, propionyl brassinolide, 24-epibrassinolide, 28-homobrassinolide, 28-epibrassinolide, 14-hydroxybrassinosteroid, which have stress resistance. However, brassinolide does not contain nutrients. When used alone, it cannot provide the nutrients required by plants. When the crop growth environment is good, the effect is not obvious. Improper use may also inhibit crop growth.

[0003] Psoralea corylifolia seed extract is a plant-derived biological pesticide product of our company, pesticide registration certificate number: PD20190058, pesticide production license number: Pesticide Shengxu (Liao) 0030, product standard number: Q / SYTX 009-2023, the relevant patents involving psoralea corylifolia seed extracts are: "Anti-plant fungal activity of psoralea corylifolia dihydroflavonoids", "Use of bakuchiol for preventing and controlling plant diseases", "Biological pesticides using psoralea corylifolia to prevent and control plant fungal diseases", "Mixed preparations of psoralea corylifolia chalcone compounds and psoralea corylifolia dihydroflavonoids for preventing and controlling plant diseases", "A psoralea corylifolia chalcone soluble liquid and its preparation method and application", "An isopsoralea corylifolia chalcone microemulsion and its preparation method", "An isopsoralea corylifolia chalcone soluble liquid 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, amino acids, etc. have the effect of preventing and controlling plant diseases and promoting plant growth; although psoralea corylifolia seed extracts and their component compounds can be used to prevent and control plant diseases and promote plant growth, the chemical composition of psoralea corylifolia seeds is complex, involving more than 90 kinds of compounds, and the active substances obtained by different extraction methods are also different, and different compounds have different activities and different targets. In addition, it is impossible to predict what kind of substances it can be combined with and what effect it can achieve. Summary of the invention

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

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

[0006] A phenol compound is 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, with a molecular formula of C 18 H 24 O, relative molecular mass: 256.4, structural formula is as follows,

[0007]

[0008] An application of the compound, application of the compound in plant regulation.

[0009] 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 3 The 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:

[0010]

[0011] 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 .

[0012] A novel plant regulator composition comprises the phenolic compound and brassinolide substances; wherein the mass ratio of the phenolic compound to the brassinolide substances is 100:1-300:1.

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

[0014] An application of the brassinolide-containing composition, and application of the composition in the preparation of a plant growth regulator.

[0015] A plant growth regulator, the regulator uses 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 agent, a wettable powder, a suspension, a soluble powder, a water-dispersible granule, an emulsifiable concentrate, a microcapsule suspension or a microemulsion.

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

[0018] 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.

[0019] An application of the plant growth regulator, wherein the plant growth regulator is used to regulate the growth of fruit trees, vegetables or grain crops, increase production and income, and improve fruit quality.

[0020] The preparation is prepared into liquid medicine of different concentrations with water and applied to the surface of crops, which can effectively promote plant growth, increase thousand-grain weight, improve yield and improve fruit variety.

[0021] Advantages and effects of the present invention:

[0022] 1. The growth-promoting effect is obvious. The efficacy of the combination is greatly improved compared with that of a single agent, and the combination of the two has a synergistic effect on plant growth regulation.

[0023] 2. Comprehensive functions. The composition can not only promote plant cell division and effectively promote plant growth, but also balance the accumulation of nutrients for crop growth, increase thousand-grain weight, increase yield, and improve fruit varieties.

[0024] 3. Controllable growth. The composition can intelligently adjust the proportion of plant protein, fat, starch and other nutrients required according to the different types of nutrients required at different stages of crop growth, and reasonably deliver them to the required parts. Avoid the passive stress absorption of plants under exogenous feeding conditions, resulting in the phenomenon of "not enough what is needed, and excess of what is not needed".

[0025] 4. Green and environmentally friendly. The combination of plant-based pesticides has no toxic side effects, and natural products are easily degraded, avoiding environmental pollution and harm to natural enemies. BRIEF DESCRIPTION OF THE DRAWINGS

[0026] 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.

[0027] 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.

[0028] 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

[0029] 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.

[0030] The present invention separates and purifies a new compound 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol, which can significantly increase the expression of light-harvesting proteins and photosynthesis-related proteins in plant chloroplasts. Further, the compound is mixed with brassinolide substances to promote plant cell division and growth, balance the accumulation of nutrients for crop growth, and synergize and complement each other in terms of target points. The mixed use of the two can complement each other in terms of function.

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

[0032] 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.

[0033] 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 above-obtained extract 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, and the content is 97.51%. Appearance: light yellow viscous liquid, molecular formula: C18H24O, relative molecular mass: 256.4, structural formula:

[0034]

[0035] 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 .

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

[0037] Weigh 1.0 g of the phenolic substance obtained in Example 1, add 0.005 g of brassinolide, 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.brassinolide soluble solution.

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

[0039] Weigh 0.5 g of the phenolic substance obtained in Example 1, add 0.002 g of propionyl brassinolide, 2 g of ethanol, and 1 g of dimethyl sulfoxide, stir until completely dissolved, then 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, stir evenly to obtain 4-2-(methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.propionyl brassinolide soluble solution.

[0040] Example 4 Preparation of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.24-epi-brassinolide soluble preparation

[0041] Weigh 0.3 g of the phenolic substance obtained in Example 1, add 0.001 g of 2,4-epi-brassinolide, 2 g of ethanol, and 1 g of dimethyl sulfoxide, stir until completely dissolved, then add 3 g of S-80, 2 g of NP-15, and 12 g of Nongru 601, 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.2,4-epi-brassinolide soluble solution.

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

[0043] Weigh 1.2 g of the phenolic substance obtained in Example 1, add 0.004 g of 28-homobrassinolide, 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.28-homobrassinolide soluble solution.

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

[0045] Weigh 0.6 g of the phenolic substance obtained in Example 1, add 0.002 g of 28-epihomobassinol lactone, add 2 g of ethanol, 1 g of dimethyl sulfoxide, stir until completely dissolved, add 3 g of T-20, 1 g of Nongru 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 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.28-epihomobassinol lactone soluble solution.

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

[0047] Weigh 1.0 g of the phenolic substance obtained in Example 1, add 0.01 g of 14-hydroxybrassinosteroid, 2 g of ethanol, and 1 g of dimethyl sulfoxide, stir until completely dissolved, then 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 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.14-hydroxybrassinosteroid soluble solution.

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

[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 a soluble solution of 4-(2-methyl-2-(4-methylpent-3-en-1-yl)cyclopent-3-en-1-yl)phenol.

[0050] Application Example 1 Experiment on the Effect on Wheat Growth and Yield

[0051] 1. Trial location

[0052] Yanzhuang Village, Suiyang District, Shangqiu City, Henan Province, the land is rotated with wheat and corn all year round. It has flat terrain, complete water conservancy facilities and fertile soil.

[0053] 2. Test Materials

[0054] The tested crop was winter wheat, variety: Zhongmai 175; the tested agents were the substances in Example 2 and Example 8.

[0055] 3. Experimental Design

[0056] The solution was sprayed on the stems and leaves at the tillering stage, the head opening stage and the full heading stage of wheat. The experiment set up 4 treatments: 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 solution 2000 mg / L (commercially available); treatment 4 (CK): blank control. The other management measures of 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. Survey items and methods

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

[0059] During the wheat maturity period, 10 holes were randomly selected from each treatment field to measure the length of the first internode at the base of the main stem, the length of the second internode at the base, the length of the internode below the ear, the ear length and the plant height. After the five-leaf stage of wheat in the field, three points were set in each treatment field to investigate the number of stem tillers in the population.

[0060] 4.2. Determination of yield and its components

[0061] Before wheat matures and is harvested, 1m 2 The number of ears was investigated at the sampling point, and another 30 plants were selected for indoor testing to determine the number of grains per ear. After the grains were dried, 1000 grains were counted and weighed. 2 After harvesting, the crops are dried naturally and weighed, and converted into yield per mu.

[0062] 5. Results and Analysis

[0063] Table 1 Effects 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, the preparation of Example 2 can effectively increase the plant height, internode spike length and tiller number after treatment, providing favorable material conditions for increasing yield.

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

[0067]

[0068] From Table 2, compared with the blank control and the common drug treatment, the preparation of Example 2 can significantly increase the number of wheat grains per ear and the thousand-grain weight, thereby increasing the wheat yield.

[0069] Application Example 2 Experiment on the Effect of Eggplant Growth and Quality

[0070] 1. Trial location

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

[0072] 2. Test Materials

[0073] The test crop was eggplant, and the variety was purple 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. The test soil was mixed evenly in a potted method and placed in a 24cm×18cm plastic pot, 2.5kg per pot. Eggplant was sown by conventional seed soaking and germination, and planted in a plastic pot after the cotyledons were unfolded. Two eggplant seedlings were planted in each plastic pot. When the eggplant seedlings had four leaves and one heart, one eggplant seedling with relatively consistent growth was retained in each pot. The spraying treatment of the agent began. The experiment set up 5 treatments, treatment 1: preparation of Example 3, concentration of 200mg / L; treatment 2: preparation of Example 8, concentration of 400mg / L; treatment 3: spraying propionyl brassinolide soluble solution (commercially available), concentration of 1000mg / L; treatment 4: Example 1 obtained psoralea corylifolia seed extract diluted 3000 times with water to obtain psoralea corylifolia plant nutrient solution; treatment 5 (CK): spraying clean water. Treatment once every 10d, a total of 3 treatments. When spraying, use a small spray bottle to spray the front and back of the eggplant leaves in a mist form, spraying until liquid droplets just fall out.

[0076] 4. Survey items and methods

[0077] Ten days after the last application of pesticides, 10 eggplant plants were randomly selected to investigate plant height, fruit setting rate of gate eggplant and pair eggplant, stem diameter, and chlorophyll content; at harvest, 10 eggplant plants were randomly selected to investigate fruit traits such as number of fruits per plant, single fruit weight, fruit length, fruit diameter, fruit shape, and glossiness. Plant height was measured with a tape measure, stem diameter was measured with a vernier caliper, and chlorophyll content (SPAD) was measured with a chlorophyll meter (SPAD-502). The mass was weighed separately each time the fruit was picked and converted into 667m2 of yield. Dry matter content was determined by drying.

[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 leaf chlorophyll content of eggplant plants, thereby promoting biomass accumulation and fruit setting rate.

[0082] Table 4 Effects of the preparations of Example 3 and Example 8 on the fruiting of eggplant

[0083]

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

[0085] Application Example 3: Experiment on the effect on watermelon growth

[0086] 1. Trial location

[0087] This is carried out in a watermelon greenhouse in Liangzhuang Town, Daiyue District, Tai'an City, Shandong Province.

[0088] 2. Test Materials

[0089] The test crop was watermelon, and the variety was Black Beauty; the test agents were the preparations of Example 4 and Example 8.

[0090] 3. Experimental Design

[0091] On the day when the female flowers of watermelon opened, randomly selected watermelon seedlings with basically the same plant size, stem thickness, number of branches, number of flowers and growth were tested. The test set up 4 treatments, treatment 1: Example 4 preparation, concentration of 300 mg / L; treatment 2: Example 8 preparation, concentration of 500 mg / L; treatment 3: 24-epi-brassinolide soluble solution (commercially available), concentration of 500 mg / L; treatment 4 (CK): spraying with clean water. The treatment was carried out once every 10 days, for a total of 3 times. The liquid was sprayed on the ovary and pedicel of the female flower, and each treatment was repeated 4 times.

[0092] 4. Survey items and methods

[0093] After the last application of pesticide, when the fruit was ripe, 5 fruits were randomly picked from each replicate to measure the single fruit weight, fruit stalk thickness and soluble solid content. The soluble solid content was determined using a WYT-handheld refractometer.

[0094] After the last application of pesticides, the growth and physiological indicators of the plants were measured when the watermelons were mature. The growth indicators measured the main vine length of the watermelon plants, the thickness of the stem at the 5th node, the length of the internode at the 5th node, and the length of the petiole of the true leaves at the 5th node. The physiological indicators measured the chlorophyll content (SPAD) of the true leaves of each watermelon plant in each plot. The watermelons were picked, and the fruit quality and yield were measured. The fruit setting rate was counted, the weight of each fruit was weighed, the yield was calculated and converted into unit yield. The total soluble solid content in the center of the watermelon fruit and the part close to the rind was measured using a handheld refractometer, the organic acid content of the fruit was detected by sodium hydroxide titration, and the vitamin C content in the fruit was determined by 2,6-dichlorophenol indigo acid titration. The sugar content in the center was measured using a saccharimeter.

[0095] 5. Results and Analysis

[0096] Table 5 Effect of watermelon growth indexes under treatment with formulations of Example 4 and Example 8

[0097]

[0098] Table 6 Effect of watermelon yield and quality under treatment with formulations of Example 4 and Example 8

[0099]

[0100]

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

[0102] Application Example 4: Experiment on the impact on citrus yield

[0103] 1. Trial location

[0104] The experiment was arranged in Meiwan Village, Shuangqiao Town, Danleng County, Meishan City. The orchard soil was 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. Experimental Design

[0108] This experiment has 4 treatments: Treatment 1: Example 5 preparation, concentration is 100 mg / L; Treatment 2: Example 8 preparation, concentration is 250 mg / L; Treatment 3: 28-homobrassinolide soluble solution (commercially available), concentration is 250 mg / L; Treatment 4 (CK): spray with water. The pesticide was applied once at the citrus flowering stage, young fruit stage and fruit expansion stage. The application method is to spray the whole plant, focusing on spraying flowers and young fruits, and the spraying amount is 1500L / hm 2 .Second-rate.

[0109] 4. Survey items and methods

[0110] After the citrus fruits mature, 3 citrus fruits (15 per plant) are randomly picked from the east, south, west, north and center of each tree, with a total of 30 fruits in each area, and the fruit diameter and single fruit weight are measured. Then, 10 of them are randomly selected for quality testing. After the sampling survey, all the fruits are harvested at one time in each area to measure the yield. The quality determination includes 4 main citrus fruit quality indicators: total sugar, total acid, soluble solids and vitamin C content. The total sugar is determined by the anthrone colorimetric method. The total acid and soluble solids are determined by the PAL-Acid1 sugar-acid integrated instrument. The vitamin C content is determined by the 2.6-dichloroindophenol method.

[0111] 5. Results and Analysis

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

[0113]

[0114] Table 8 Measurement results of citrus quality under treatment with formulations in Example 5 and Example 8

[0115]

[0116] Tables 7 and 8 show that spraying the formulation of Example 5 on the leaves of citrus during the flowering stage, young fruit stage and fruit expansion stage can increase the fruit diameter, increase the single fruit weight, and improve the yield, and all have a significant improvement on the fruit quality.

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

[0118] 1. Trial location

[0119] The experiment was conducted in a vegetable field in Xiuling Village, Gushan Town, Jin'an District, Fuzhou City. The test site is 20m above sea level and has sandy loam soil with medium to high fertility.

[0120] 2. Test Materials

[0121] The crop is tomato, and the variety is Imperial Red Cherry; the test agents are the preparations of Example 6 and Example 8.

[0122] 3. Experimental Design

[0123] This experiment has 4 treatments: Treatment 1: Example 6 preparation, concentration is 100 mg / L; Treatment 2: Example 8 preparation, concentration is 200 mg / L; Treatment 3: 28-epihomobrassinolide soluble solution (commercially available), concentration is 200 mg / L; Treatment 4 (CK): spraying with water. The first application of the drug was 7 days before tomato flowering, the second application during the flowering period, and the third application was 7 days after the interval, that is, during the tomato flowering and fruiting period, with a spray volume of 750 kg / hm 2 When applying pesticides, use ground film as a barrier to prevent droplets from drifting.

[0124] 4. Survey items and methods

[0125] Fruit setting rate survey: During the tomato fruit setting period, the fruit setting rate of each plot was investigated. Ten tomato plants were checked in each plot. The parallel line sampling method was used. The total number of flowers of three representative inflorescences of each plant was checked. The total number of fruits was investigated and the fruit setting rate was calculated.

[0126] Yield survey: Yield measurement is carried out after tomato harvest. Tomatoes are harvested as they gradually mature, and the harvest amount of each plot is recorded each time. The amount of tomatoes picked five times in a row is converted into yield per hectare.

[0127] Quality determination: When tomatoes are harvested for the first time, check 10 plants in each plot and randomly select two fruits from each plant, i.e. 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 formulations of Example 6 and Example 8 on tomato fruit setting rate, yield and quality

[0130]

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

[0132] Application Example 6 Experiment on the Effect on Corn Growth

[0133] 1. Trial location

[0134] The experiment was conducted in a corn field in Liji Township, Shangcheng County, Xinyang City, Henan Province. The previous crop was wheat and the soil was moderately fertile.

[0135] 2. Test Materials

[0136] The corn variety was Zhengdan 958; the tested agents were the preparations of Example 7 and Example 8.

[0137] 3. Experimental Design

[0138] This experiment has 4 treatments, treatment 1: Example 7 preparation, concentration is 300mg / L; treatment 2: Example 8 preparation, concentration is 600mg / L; treatment 3: 4-hydroxybrassinosteroid soluble solution (commercially available), concentration is 600mg / L; treatment 4 (CK): spray with water. The first application of pesticide was carried out at the seedling stage of corn (6-7 leaves), and the second application of pesticide was carried out at the corn trumpet stage. The Dayuan brand 3WBD-16 backpack electric sprayer was used for pesticide application, and the spray plate aperture was 1.4-1.6mm. 30kg of water was added per mu according to the dosage, and the solution was prepared and sprayed.

[0139] 4. Survey items and methods

[0140] The plant height, stem thickness and ear height of corn were measured before harvesting, and the yield was measured at harvesting. The five-point sampling method was adopted, 5 points were selected in each plot, 2 plants were surveyed at each point, and the plant height, stem thickness and ear height of 10 corn plants were measured. The leaf color was observed to understand whether the plants were deformed. 10 mature fresh sticks were collected and the soluble sugar content was determined with a handheld refractometer. The yield determination was to measure the yield of all plants in each plot, and then convert it into per mu yield to calculate the yield increase rate. Plant height and ear height were measured with a meter ruler, and stem thickness was measured with a vernier caliper.

[0141] 5. Results and Analysis

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

[0143]

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

Claims

1. A phenol 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, structural formula is as follows, 2. Use of the compound according to claim 1, characterized in that: The compounds are used in plant regulation.

3. A novel plant regulator composition, characterized in that: The composition is the phenolic compound and brassinolide substance as described in claim 1; wherein the mass ratio of the phenolic compound to the brassinolide substance is 100:1-300:

1.

4. The brassinolide-containing composition according to claim 3, characterized in that: The brassinolide substance is one or more of brassinolide, propionyl brassinolide, 24-epibrassinolide, 28-homobrassinolide, 28-epihomobrassinolide, and 14-hydroxybrassinosteroid.

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

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

7. The plant growth regulator according to claim 6, characterized in that: The plant 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.

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

9. Use of the plant growth regulator according to claim 6, characterized in that: The plant regulator is used in regulating the growth of fruit trees, vegetables or grain crops, increasing production and income, and improving fruit quality.

Images