Furanone ether derivative as well as preparation method and application thereof

Abstract

The invention relates to the technical field of plant growth regulators, in particular to a furanone ether derivative as well as a preparation method and application thereof. The invention provides a furanone ether derivative, which has a structure as shown in the following formula I: # imgabs0 #, in which R1 is a monosubstituted or polysubstituted group on a benzene ring and is selected from halogen, C1-C3 alkyl, C1-C3 alkoxy and nitryl; r2 is selected from H and methyl, and R3 is selected from H and phenyl. The invention provides the furanone ether derivative with the effect of regulating plant growth, the synthesis route is simple, the yield is high, and large-scale development and application of the furanone ether derivative in the field of plant growth regulators are facilitated.

Description

Technical Field

[0001] The present invention relates to the technical field of plant growth regulators, and in particular to a furanone ether derivative, a preparation method thereof, and an application thereof. Background Art

[0002] Plant hormones are natural organic compounds synthesized in plants. Trace amounts of plant hormones can regulate the process of plant growth and development by themselves and play different roles at various stages of their growth. Currently, six major types of natural hormones produced in plants are known, namely auxin, cytokinin (CTK), brassinosteroid (BR), gibberellin (GA), abscisic acid (ABA), and ethylene. In addition, substances such as salicylic acid (SA), jasmonic acid (JA), and strigolactones (SLs) have also been proven to play the role of plant hormones in recent years.

[0003] SLs is a general term for natural strigolactones and their synthetic analogs. It is a sesquiterpene compound, and the basic unit is isoprene. In recent years, more and more experimental results have proved that SLs is a new type of plant hormone with biological functions such as promoting plant seed germination and inhibiting plant branching. These important biological activities make SLs have good application prospects.

[0004] Although natural SLs have good physiological activities, the content of natural SLs in plants is extremely low and it is difficult to extract. Therefore, chemical synthesis is currently the main method for obtaining strigolactones. GR24 is the first synthetic SLs analog with good biological activity. However, the current synthetic SLs analogs also have problems such as large synthesis difficulty, high raw material cost, and low yield, and cannot be prepared on a large scale for use, which limits the large-scale promotion and application of synthetic SLs analogs in agricultural production.

[0005] In view of this, the present invention is specifically proposed. Summary of the Invention

[0006] The object of the present invention is to provide a furanone ether derivative, a preparation method thereof, and an application thereof. The furanone ether derivative of the present invention has the function of regulating plant growth, and at the same time has a simple synthesis route and high yield, which is beneficial to its large-scale development and application in the field of plant growth regulators.

[0007] In order to achieve the above object of the present invention, the first aspect of the present invention provides a furanone ether derivative having the structure shown in the following formula I:

[0008]

[0009] Among them, R1 is a mono- or poly-substituted group on the benzene ring, selected from halogen, C1-C3 alkyl, C1-C3 alkoxy, and nitro; R2 is selected from H and methyl, and R3 is selected from H and phenyl.

[0010] In a specific embodiment of the present invention, when R2 is H, R3 is phenyl.

[0011] In a specific embodiment of the present invention, when R2 is methyl, R3 is H.

[0012] In a specific embodiment of the present invention, the furanone ether derivative is any one of the following compounds:

[0013]

[0014]

[0015] The second aspect of the present invention provides a preparation method of the furanone ether derivative provided in the first aspect of the present invention, including the following steps: Compound A and Compound B react in a solvent under the action of a catalyst; the structures of Compound A and Compound B are as follows:

[0016]

[0017] In a specific embodiment of the present invention, the solvent includes toluene.

[0018] In a specific embodiment of the present invention, the catalyst includes p-toluenesulfonic acid.

[0019] In a specific embodiment of the present invention, the temperature of the reaction is 70-90 °C.

[0020] In a specific embodiment of the present invention, the molar ratio of Compound A to Compound B is (1-2):1.

[0021] In a specific embodiment of the present invention, Compound B includes any one of the following structures:

[0022]

[0023] In a specific embodiment of the present invention, the preparation of Compound B1 includes: pyruvic acid and acetone react under the action of phosphoric acid. Further, the molar ratio of pyruvic acid to acetone is 1:(2-3).

[0024] In a specific embodiment of the present invention, the preparation of Compound B2 includes: pyruvic acid and phenylalanine react in water. Further, the molar ratio of pyruvic acid to phenylalanine is 1:(0.08-0.15).

[0025] The third aspect of the present invention provides the use of the furanone ether derivatives provided in the first aspect of the present invention in the preparation of plant growth regulators.

[0026] In a specific embodiment of the present invention, the plant growth regulator is used for at least one of promoting plant seed germination, inhibiting plant tillering, and promoting plant defoliation.

[0027] In a specific embodiment of the present invention, the plants include at least one of Orobanche cumana Wallr., Cynomorium songaricum Rupr., wheat, and cotton.

[0028] The fourth aspect of the present invention provides a plant growth regulator, comprising the furanone ether derivatives provided in the first aspect of the present invention.

[0029] Compared with the prior art, the beneficial effects of the present invention are as follows:

[0030] The present invention provides a furanone ether derivative having the function of regulating plant growth, and at the same time, the synthesis route is simple and the yield is high, which is beneficial to its large-scale development and application in the field of plant growth regulators. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] In order to more clearly illustrate the specific embodiments of the present invention or the technical solutions in the prior art, the following will briefly introduce the drawings required for use in the description of the specific embodiments or the prior art. Obviously, the drawings in the following description are some embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained based on these drawings without creative efforts.

[0032] Figure 1 It is a comparative diagram of the effects of different compounds provided in the embodiments of the present invention on the germination of Cynomorium songaricum Rupr. seeds;

[0033] Figure 2 It is a comparative diagram of the effects of different compounds provided in the embodiments of the present invention on the tillering of wheat;

[0034] Figure 3 It is a comparative diagram of the effects of different compounds provided in the embodiments of the present invention on the defoliation of cotton. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0035] The technical solutions of the present invention will be clearly and completely described below in conjunction with the accompanying drawings and specific embodiments. However, those skilled in the art will understand that the following described embodiments are some embodiments of the present invention, rather than all embodiments, and are only used to illustrate the present invention and should not be construed as limiting the scope of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative efforts shall fall within the scope of protection of the present invention. For those conditions not specified in the embodiments, they are carried out according to conventional conditions or conditions recommended by the manufacturer. Those reagents or instruments not indicated by the manufacturer can be obtained as conventional products through commercial purchase.

[0036] The first aspect of the present invention provides furanone ether derivatives, having the structure shown in the following formula I:

[0037]

[0038] Among them, R1 is a mono-substituted or multi-substituted group on the benzene ring, selected from halogen, C1-C3 alkyl, C1-C3 alkoxy and nitro; R2 is selected from H and methyl, and R3 is selected from H and phenyl.

[0039] R1 being a mono-substituted or multi-substituted group on the benzene ring means that on the benzene ring where R1 is located, there can be one R1 substituent or more than two (such as 2, 3, 4 or 5) R1 substituents.

[0040] C1-C3 alkyl refers to a straight-chain or branched-chain hydrocarbon group with 1 to 3 carbon atoms composed only of carbon atoms and hydrogen atoms, and can include, for example: methyl, ethyl, propyl and isopropyl; C1-C3 alkoxy can include methoxy, ethoxy, propoxy and isopropoxy; halogen includes at least one of fluorine (F), chlorine (Cl) and bromine (Br).

[0041] In the specific embodiment of the present invention, when R2 is H, R3 is phenyl. The structural formula of the corresponding furanone ether derivative is specifically as follows:

[0042]

[0043] In the specific embodiment of the present invention, when R2 is methyl, R3 is H. The structural formula of the corresponding furanone ether derivative is specifically as follows:

[0044]

[0045] In the specific embodiment of the present invention, the furanone ether derivative is any one of the following compounds:

[0046]

[0047]

[0048] In a specific embodiment of the present invention, the furanone ether derivative is any one of the following compounds:

[0049]

[0050] The second aspect of the present invention provides a preparation method of the furanone ether derivative provided in the first aspect of the present invention, including the following steps: compound A and compound B react in a solvent under the action of a catalyst; the structures of compound A and compound B are as follows:

[0051]

[0052] The synthesis route of the furanone ether derivative is as follows for reference:

[0053]

[0054] In a specific embodiment of the present invention, the solvent includes toluene. The amount of the solvent can be adjusted conventionally according to the reaction system to ensure the dissolution of the raw materials. For example, the ratio of toluene to compound B can be (20 - 40) mL﹕1 g, that is, compared with 1 g of compound B, the amount of toluene used can be 20 - 40 mL, but it is not limited thereto.

[0055] In a specific embodiment of the present invention, the catalyst includes p-toluenesulfonic acid. Further, the amount of the catalyst is 1% - 10% of the mass of compound B. For example, it can be 1%, 3%, 5%, 8%, 10% or the range composed of any two of them. In actual operation, p-toluenesulfonic acid can be added in the form of p-toluenesulfonic acid monohydrate.

[0056] In a specific embodiment of the present invention, the reaction temperature is 70 - 90 °C. For example, it can be 70 °C, 75 °C, 80 °C, 85 °C, 90 °C or the range composed of any two of them, which is more helpful for taking into account the reaction efficiency and yield, etc. Further, the specific reaction time is adjusted conventionally by TLC monitoring. For example, the reaction time of this step of the present invention can be 16 - 30 h, but it is not limited thereto.

[0057] In a specific embodiment of the present invention, the molar ratio of compound A to compound B is (1 - 2)﹕1. For example, it can be 1﹕1, 1.2﹕1, 1.5﹕1, 1.8﹕1, 2﹕1 or the range composed of any two of them.

[0058] In a specific embodiment of the present invention, it further includes: after the reaction is completed, the solvent in the reaction system is removed, then extracted with ethyl acetate, the organic phase is collected, and purified by column chromatography.

[0059] In actual operation, the reaction of compound A and compound B may include the following steps:

[0060] After mixing compound B with a solvent, a catalyst is added, and then compound A is added. Stir to dissolve compound A, then raise the temperature to the reaction temperature for reaction, and monitor the reaction progress according to TLC; after the reaction is completed, the solvent is removed by distillation under reduced pressure, then extracted with ethyl acetate, the organic phase is collected, and after concentration, it is purified by column chromatography. In column chromatography purification, the eluent can be petroleum ether and ethyl acetate, but is not limited thereto.

[0061] In a specific embodiment of the present invention, compound B includes any one of the following structures:

[0062]

[0063] Compound A and compound B used in the present invention can be obtained by external purchase or self-preparation. For example, if prepared by self-preparation, the following route can be referred to for preparation.

[0064] In a specific embodiment of the present invention, the preparation of compound B1 includes: pyruvic acid and acetone react under the action of phosphoric acid. Further, the molar ratio of pyruvic acid to acetone is 1﹕(2 - 3). The specific route is as follows:

[0065]

[0066] Specifically, the preparation of compound B1 includes: weighing 5 g (56.78 mmol) of pyruvic acid, 7.90 g (136 mmol) of acetone, and 18.74 g (162 mmol) of phosphoric acid (85% aqueous solution) respectively, and adding them to a 250 mL round-bottom flask in sequence. Stir magnetically to make the raw materials fully contact, and then raise the temperature to 98 °C for reaction. Monitor the reaction by TLC [V 石油醚 ﹕V 乙酸乙酯 = 2﹕1]. After 24 h, the reaction is completed. Extract with ethyl acetate 30 mL × 3, combine the organic phases, dry with anhydrous sodium sulfate, filter by suction, and then concentrate under reduced pressure on a rotary evaporator. After purification by column chromatography (the eluent is V 石油醚 ﹕V 乙酸乙酯 = 2﹕1), compound B1 is obtained as a white solid with a yield of 55.02%.

[0067] In a specific embodiment of the present invention, the preparation of compound B2 includes: pyruvic acid and phenylalanine react in water. Further, the molar ratio of pyruvic acid to phenylalanine is 1﹕(0.08 - 0.15). The specific route is as follows:

[0068]

[0069] Specifically, the preparation of compound B2 includes: weighing 6.6 g (40 mmol) of phenylalanine and 35.2 g (400 mmol) of pyruvic acid separately, adding them into a 250 mL round-bottom flask in sequence, adding 10 mL of water, and magnetically stirring to dissolve and fully contact them, and heating under reflux at 80 °C for reaction. TLC [V 石油醚 ﹕V 乙酸乙酯 =2﹕1] was used to monitor the reaction. After 24 h, the reaction ended. It was extracted with ethyl acetate three times with 30 mL each time. The organic phases were combined, dried with anhydrous sodium sulfate, filtered by suction, and concentrated under reduced pressure using a rotary evaporator. It was purified by column chromatography (the eluting phase was V 石油醚 ﹕V 乙酸乙酯 =2﹕1), and compound B2 was obtained as a white solid with a yield of about 48.7%.

[0070] The third aspect of the present invention provides the application of the furanone ether derivatives provided in the first aspect of the present invention in the preparation of plant growth regulators.

[0071] In the specific embodiments of the present invention, the plant growth regulator is used for at least one of promoting plant seed germination, inhibiting plant tillering, and promoting plant defoliation.

[0072] In the specific embodiments of the present invention, the plants include at least one of Orobanche cumana Wallr., Cynomorium songaricum Rupr., wheat, and cotton.

[0073] Specifically, the plant growth regulator prepared from the furanone ether derivatives of the present invention can promote the germination of Orobanche cumana Wallr. seeds; can promote the germination of Cynomorium songaricum Rupr. seeds; can inhibit wheat tillering; can promote cotton defoliation.

[0074] For example, when the plant growth regulator prepared from the furanone ether derivatives of the present invention is used to promote the germination of Orobanche cumana Wallr. seeds, preferably the furanone ether derivatives include at least one of the following structures:

[0075]

[0076] More preferably, it includes at least one of the following structures:

[0077]

[0078] For example, when the plant growth regulator prepared from the furanone ether derivatives of the present invention is used to promote the germination of Cynomorium songaricum Rupr. seeds, preferably the furanone ether derivatives include at least one of the following structures:

[0079]

[0080] More preferably, it includes the following structure:

[0081]

[0082] For example, when the plant growth regulator prepared from the furanone ether derivatives of the present invention is used to inhibit wheat tillering, the furanone ether derivatives preferably include at least one of the following structures:

[0083]

[0084] For example, when the plant growth regulator prepared from the furanone ether derivatives of the present invention is used to promote cotton leaf fall, the furanone ether derivatives preferably include at least one of the following structures:

[0085]

[0086]

[0087] The fourth aspect of the present invention provides a plant growth regulator, comprising the furanone ether derivative provided by the first aspect of the present invention.

[0088] Example 1

[0089] This example provides a method for preparing compound M1, comprising the following steps:

[0090] Weigh 1 g of compound B1 into a 250 mL round-bottom flask, add 30 mL of toluene to dissolve, add 50 mg (0.26 mmol) of p-toluenesulfonic acid monohydrate, and then add 1.27 g (8.76 mmol) of 4-chlorobenzenethiol, stir magnetically to dissolve and fully contact, and heat under reflux at 80°C to react. TLC[V 石油醚 :V 乙酸乙酯 =10﹕1] to monitor the reaction. After 24 hours, the reaction was completed, and the toluene was removed by vacuum distillation on a rotary evaporator. 30 mL × 3 of ethyl acetate was used for extraction. The organic phases were combined, dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure on a rotary evaporator, and purified by column chromatography. The elution phase was V 石油醚 :V 乙酸乙酯 =15:1, an orange oily liquid M1 was obtained with a yield of 51.03%.

[0091] Example 2

[0092] This example provides a method for preparing compound P1, comprising the following steps:

[0093] Weigh 1 g of compound B2 into a 250 mL round-bottom flask, add 30 mL of toluene to dissolve, add 50 mg (0.26 mmol) of p-toluenesulfonic acid monohydrate, and then add 1.27 g (8.76 mmol) of 3-chlorobenzenethiol, stir magnetically to dissolve and fully contact, and heat under reflux at 80°C to react. TLC[V 石油醚 :V乙酸乙酯 = 10:1] Detection reaction. After 24 h, the reaction ended. Under a rotary evaporator, vacuum distillation was carried out to remove toluene. Ethyl acetate was used for extraction (30 mL × 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered by suction, and then concentrated under reduced pressure under a rotary evaporator. Purification was carried out by column chromatography, and the eluent was V 石油醚 :V 乙酸乙酯 = 10:1, and a yellow oily liquid P1 was obtained with a yield of 53.80%.

[0094] Referring to the preparation methods of Example 1 and Example 2 and replacing the corresponding reaction raw materials, other corresponding compounds in Table 1 can be prepared. The corresponding structures and characterization data are shown in Table 2.

[0095] Table 1 Physical and chemical data of each compound

[0096]

[0097]

[0098] Note: In the replacement of reaction raw materials, M2 - M13 replaced 4-chlorothiophenol in the preparation step of M1 in equimolar amounts; P2 - P12 replaced 3-chlorothiophenol in the preparation step of P1 in equimolar amounts.

[0099] Table 2 Chemical structures of each compound and 1 H NMR,[[]] 13 C NMR and HRMS data

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] Experimental Example

[0108] Test materials and test agents

[0109] Active test seeds: Orobanche cumana seeds, Cynomorium songaricum seeds, Cistanche deserticola seeds, cotton seeds, wheat seeds.

[0110] Test utensils: filter paper, glass fiber filter paper, disposable culture dishes.

[0111] Test reagents: agar, sterile water, ethanol, sodium hypochlorite.

[0112] Control agent: rac-GR24.

[0113] Test instruments

[0114] Vertical automatic pressure steam sterilizer, ultra-clean workbench (ZHJH-C1109C).

[0115] Cultivation treatment

[0116] 1. Determination of the germination activity of Orobanche cumana Wallr. seeds

[0117] (1) Seed disinfection treatment: Before the experiment, disinfect the Orobanche cumana Wallr. seeds, shake them with 70% (v / v) ethanol for 1 min, then shake them with 0.5% sodium hypochlorite for 15 min, and finally rinse them repeatedly with sterile water, place them on filter paper, and air-dry them naturally in the ultra-clean workbench.

[0118] (2) Preparation of solutions: Gradiently dilute each synthesized compound to be tested with ethanol to a test solution with a concentration of 10 -5 ~10 -9 mol / L.

[0119] (3) Activity test treatment: Lay filter paper of appropriate size on the bottom layer of a petri dish with a diameter d = 9 cm, add 1 mL of sterile water to the filter paper so that it fits completely with the petri dish. Place 6 glass fiber filter papers with a diameter d = 13 mm evenly in each petri dish, sow seeds on the glass fiber filter papers, and place 30 - 80 seeds evenly on each piece. Finally, add the test solution containing the compound. Set 6 replicate tests for each treatment. Seal the petri dish and place it in the dark at 25 - 26 °C for cultivation. Among them, the positive control group is rac-GR24 (a racemic mixture of (2’r) and (2’s)), and the negative control group is pure water.

[0120] (4) Data processing: After 14 days of cultivation, observe and record the number of root buds under a microscope. Use Origin 2019b software to process the data and obtain the effective concentration (EC 50 ) values. The obtained results are shown in Table 3.

[0121] 2. Determination of the germination activity of Cynomorium songaricum Rupr. and Cistanche deserticola Ma seeds

[0122] (1) Seed disinfection treatment: Before the experiment, Cynomorium songaricum and Cistanche deserticola seeds were disinfected by shaking with 70% (v / v) ethanol for 1 min, then shaking with 0.5% sodium hypochlorite for 15 min, and finally rinsing repeatedly with sterile water, placing on filter paper, and air-drying naturally in a laminar flow hood.

[0123] (2) Solution preparation: Each synthesized test compound was diluted with ethanol to a test solution with a concentration of 10 -3 mol / L.

[0124] (3) Culture medium preparation: Weigh 0.7 g of agar, add deionized water and make up the volume to 100 mL. The prepared liquid culture medium was respectively filled into conical flasks and placed in an autoclave for high-temperature sterilization. The prepared test compound solution was added to the sterilized liquid culture medium to prepare a liquid culture medium containing the test compound (60 °C), and the compound concentration was 10 -5 mol / L. The culture medium was respectively poured into petri dishes (diameter d = 9 cm), and after being placed until the culture medium cooled and solidified, plate culture was carried out.

[0125] (4) Activity experiment treatment: 30 - 40 Cynomorium songaricum seeds and Cistanche deserticola seeds were respectively placed in the cooled and solidified petri dishes. Six replicate experiments were set for each treatment. After sealing the petri dishes, they were placed in an incubator at 25 °C under constant temperature and dark conditions for cultivation. Among them, the positive control group was rac-GR24 (a racemic mixture of (2’r) and (2’s)), and the negative control group was pure water.

[0126] (5) Data processing: After 14 days of cultivation, the number of root buds was observed and recorded. IBM SPSS Statistics 26 software was used to process the data, perform error analysis and significant difference analysis, and Origin 2019b software was used to draw charts. The obtained results are shown in Table 4.

[0127] 3. Wheat tillering activity determination

[0128] (1) Seed disinfection treatment: Select 400 wheat seeds with uniform size and plump grains. The seeds were soaked in a 10% H2O2 aqueous solution for disinfection for 15 min, then the seeds were rinsed repeatedly with sterile water, and finally sterile water was added to cover the seeds and soaked for germination for 24 h.

[0129] (2) Solution preparation: Each synthesized test compound was diluted with ethanol to a test solution with a concentration of 10 -6 mol / L, and 30 μL of surfactant solution was added; among them, the preparation of the surfactant solution included: weighing 0.3 g of 700# emulsifier, 0.1 g of silicone defoamer and 500 μL of anhydrous ethanol, adding to deionized water and making up the volume to 10 g.

[0130] (3) Activity test treatment: Sow the germinated seeds in pots. When the wheat seedlings grow to the two-leaf and one-heart stage, spray the prepared solution on the leaf surface. Apply the medicine once every 7 days for 3 consecutive times. When the wheat seedlings grow to the four-leaf and one-heart stage, check the tillering rate of wheat. Set 3 replicate experiments for each treatment. Among them, the positive control group is rac-GR24 (a racemic mixture of (2’r) and (2’s)), and the negative control group is pure water.

[0131] (4) Data processing: After spraying the medicine three times, record the tillering numbers on the 7th day, 14th day, and 21st day respectively. Use IBM SPSS Statistics 26 software to process the data, conduct error analysis and significance difference analysis, and use Origin 2019b software to draw charts. The obtained results are shown in Table 5.

[0132] 4. Determination of cotton defoliation activity

[0133] (1) Seed disinfection: Select 100 cotton seeds with uniform size and plump grains. Immerse the seeds in a 10% H2O2 aqueous solution for 15 minutes for disinfection, then rinse the seeds repeatedly with sterile water, and finally add sterile water to cover the seeds and soak them for germination for 24 hours.

[0134] (2) Prepare the solution: Prepare an ethephon mixed solution with a concentration of 25 μM for each synthesized compound to be tested.

[0135] (3) Activity test treatment: Sow the germinated seeds in pots. When the cotton seedlings grow to the two-leaf and one-heart stage, spray the prepared solution on the leaf surface. Apply the medicine once every 7 days for 3 consecutive times. Regularly observe the state of cotton leaves. Set 3 replicate experiments for each treatment. Among them, the positive control group is a mixed solution of 25 μM GR24 and ethephon, and the negative control group is pure water.

[0136] (4) Data processing: After spraying the medicine three times, record the number of defoliated cotton leaves respectively. Use IBM SPSS Statistics 26 software to process the data, conduct error analysis and significance difference analysis, and use Origin 2019b software to draw charts. The obtained results are shown in Table 6.

[0137] Table 3 Test results of the effects of different compounds on the germination activity of Orobanche cumana seeds

[0138]

[0139] As can be seen from the above test results, compounds M2, M3, M9, and M11 all have the activity of promoting the germination of Orobanche cumana seeds, and the EC 50 values are 5.084e -8mol / L, 6.014e -8 mol / L, 9.760e -8 mol / L, 1.330e -8 mol / L, the activity was comparable to that of the positive control GR24 (EC 50 value was 1.544e -8 mol / L) (p < 0.01). The EC 50 value of compound M1 was 5.477e -9 mol / L, one order of magnitude lower than that of the positive control GR24, and it had a good promoting effect on the germination of Orobanche cumana seeds.

[0140] Compounds P3, P5, P8, and P10 all had the activity of promoting the germination of Orobanche cumana seeds, and their EC 50 values were 8.830e -8 mol / L, 9.410e -8 mol / L, 2.896e -8 mol / L, and 1.592e -8 mol / L respectively, and the activity was comparable to that of the positive control GR24 (p < 0.01). The EC 50 values of compounds P2 and P11 were 6.150e -9 mol / L and 4.343e -9 mol / L respectively, one order of magnitude lower than that of the positive control GR24, and they had a good promoting effect on the germination of Orobanche cumana seeds.

[0141] Table 4 Test results of the effects of different compounds on the germination activities of Cynomorium songaricum and Cistanche deserticola seeds

[0142]

[0143] According to the activity results of the compounds on the germination of Orobanche cumana seeds, compounds with better activities were selected to further determine the germination of Cynomorium songaricum and Cistanche deserticola seeds. As can be seen from the above table, when the concentration of the compounds was 10 -6 mol / L, the germination rates of compounds M1, M3, and compounds P2, P10, and P11 were 38.23%, 31.50%, 32.50%, 34.91%, and 33.52% respectively, which were at the same level as 34.15% of GR24, and had a certain effect on promoting the germination of Cynomorium songaricum seeds.

[0144] However, at the same concentration, the germination process of Cistanche deserticola seeds was not stimulated by any of the compounds, and none of the compounds showed physiological activity. After analyzing the reasons in the experiment, it may be that Cistanche deserticola seeds were insensitive to the two series of compounds designed and synthesized, or insensitive to the drug with a concentration of 10 -6 mol / L.

[0145] Error analysis and significance difference analysis were carried out on the data in Table 4 (different lowercase letters indicate significant differences between samples, P < 0.05). The results are as Figure 1 shown. There was no significant difference in the activities of compounds M3, P2, P10, and P11 compared with GR24, and they had comparable biological activities with GR24. Among them, the activity of compound M1 was superior to that of GR24.

[0146] Test results of the effects of different compounds on wheat tillering

[0147]

[0148]

[0149] As can be seen from the above table, the tillering rates of compound M1, compounds P8 and P11 were 148%, 139%, and 141% respectively. Compared with the tillering rate of CK (174%), they had obvious inhibitory effects. Good physiological activities of inhibiting wheat tillering were shown in the tillering data recorded each time, and they had continuous effects. The tillering rate was about 30% lower than that of the blank control group and was at the same level as the positive control group GR24, with comparable activities.

[0150] Error analysis and significance difference analysis were carried out on the data in Table 5 (different lowercase letters indicate significant differences between samples, P < 0.05). The results are as Figure 2 shown. There was no significant difference in the activities of compounds M1, P8, and P11 compared with GR24, and they had comparable biological activities with GR24.

[0151] Test results of the effects of different compounds on cotton defoliation activity

[0152]

[0153]

[0154] As can be seen from the above table, the defoliation rates of cotton treated with compounds M1 and M3 were 66.27% and 63.89% respectively. The defoliation rates of cotton treated with compounds P2, P3, and P11 were 61.67%, 73.89%, and 67.22% respectively, which were superior to the defoliation rate of the positive control group ethephon + GR24 (58.89%), showing good promotion effects.

[0155] Error analysis and significance difference analysis were carried out on the data in Table 6 (different lowercase letters indicate significant differences between samples, P < 0.05). The results are as Figure 3 shown. There was no significant difference in the activities of compounds M1, M3, P2, P3, and P11 compared with GR24, and they had comparable biological activities with GR24.

[0156] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention, rather than to limit them; although the present invention has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that they can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements on some or all of the technical features; and these modifications or replacements do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. A furanone ether derivative, characterized in that: It has the structure shown in the following formula I: Wherein, R1 is a monosubstituted or polysubstituted group on the benzene ring, selected from halogen, C1-C3 alkyl, C1-C3 alkoxy and nitro; R2 is selected from H and methyl, and R3 is selected from H and phenyl.

2. The furanone ether derivative according to claim 1, characterized in that: When R2 is H, R3 is phenyl; Alternatively, when R2 is methyl, R3 is H.

3. The furanone ether derivative according to claim 1, characterized in that: The furanone ether derivative is any one of the following compounds:

4. The method for preparing the furanone ether derivative according to any one of claims 1 to 3, characterized in that: The method comprises the following steps: Compound A and Compound B react in a solvent under the action of a catalyst; the structures of Compound A and Compound B are as follows:

5. The preparation method according to claim 4, characterized in that: Having at least one of the following characteristics: (1) The solvent includes toluene; (2) The catalyst comprises p-toluenesulfonic acid; (3) The reaction temperature is 70 to 90° C.; (4) The molar ratio of compound A to compound B is (1-2):

1.

6. The preparation method according to claim 4, characterized in that: The compound B includes any one of the following structures:

7. Use of the furanone ether derivative according to any one of claims 1 to 3 in the preparation of plant growth regulators.

8. The use according to claim 7, characterized in that: The plant growth regulator is used for at least one of promoting plant seed germination, inhibiting plant tillering and promoting plant defoliation.

9. The use according to claim 8, characterized in that: The plant comprises at least one of sunflower, Orobanche deserticola, Cynomorium songaricum, wheat and cotton.

10. A plant growth regulator, characterized in that The invention comprises the furanone ether derivatives according to any one of claims 1 to 3.

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