CN112979622A - Compound capable of bidirectionally regulating plant growth and preparation method thereof - Google Patents
Compound capable of bidirectionally regulating plant growth and preparation method thereof Download PDFInfo
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- CN112979622A CN112979622A CN202110095671.0A CN202110095671A CN112979622A CN 112979622 A CN112979622 A CN 112979622A CN 202110095671 A CN202110095671 A CN 202110095671A CN 112979622 A CN112979622 A CN 112979622A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
- A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
Abstract
The invention discloses a compound capable of bidirectionally regulating plant growth and a preparation method thereof, and particularly relates to the technical field of plant growth, wherein the compound has a structural general formula shown in formula (1). The compound provided by the invention has a novel structure, is not recorded in the prior art, can be used for preparing a growth regulator for regulating and controlling the growth of main roots and lateral roots of plants under the condition of different concentrations, and can inhibit the main roots and promote the growth of fibrous roots in micromolar. At nanomolar, only the growth of fibrous root is promoted, and the main root is not affected. Can be specifically regulated according to the growth requirements of different plants.
Description
Technical Field
The invention relates to the technical field of plant growth, in particular to a compound capable of bidirectionally regulating plant growth and a preparation method thereof.
Background
Strigolactones (SLs) are a novel class of plant hormones, which are generic terms of natural strigol compounds and synthetic analogs, widely present in higher plants, mainly synthesized in roots. With the continuous and deep research, many biological functions of the SLs are discovered, the SLs can induce the parasitic seeds to germinate and can also play a role of a signal molecule, namely the SLs can be used as a branching factor of symbiotic arbuscular mycorrhizal fungi to promote the branching of the symbiotic arbuscular fungi. In addition, the SLs can inhibit the growth of branches and lateral buds of plants and participate in regulating and controlling the number of branches of the plants as a novel plant growth regulator, which is the most important biological function of the SLs. SLs can control plant branching, regulate and control the growth of plant root systems, promote the formation of root nodule bacteria of leguminous plants and the like through the synergistic effect of SLs and other auxin and cytokinin in plant bodies. The discovery of strigolactone and the research of the biological function thereof, particularly the research of the biological function mechanism thereof, promote the application research of strigolactone in the aspect of agriculture, SLs can effectively trap and kill parasitic weeds, improve the soil fertility, improve the resistance of plants to root-knot nematodes, regulate plant types and improve the crop yield, are green and natural plant growth regulators, and have wide application prospect. Therefore, research on the action mechanism of SLs on plant biological functions, synthesis and function research of SLs analogs, application and popularization of SLs and the like is a research hotspot in the fields of plant science and molecular biology at present.
During the planting process of the Chinese medicinal plants, part of the medicinal parts of the plants are usually at the root, such as ginseng, angelica, polygonatum, and the like. In response to the above problems, many growth regulators have been introduced to promote the growth of plant roots. However, during the growth of a plant root system, the lateral roots, if not effectively grown, can affect the growth rate of the plant. However, when a lateral root growth regulator is applied to a plant, the growth of the main root is not compatible, and the operation of applying a plurality of growth regulators is troublesome. Therefore, how to realize the regulation and control of different plant growth processes through a single growth regulator is a technical problem to be solved urgently.
Disclosure of Invention
The invention aims to provide a compound capable of bidirectionally regulating plant growth and a preparation method thereof, wherein the compound has the advantages of novel structure and capability of being used for preparing a growth regulator for regulating and controlling the growth conditions of main roots and lateral roots of plants under the condition of different concentrations.
In order to achieve the purpose, the invention provides the following technical scheme:
a compound capable of bidirectionally regulating plant growth, the structural general formula is as shown in formula (1):
the invention also provides a plant lateral root growth promoting regulator prepared by applying the compound, wherein the solvent of the regulator is dimethyl sulfoxide, and the concentration of the regulator is 1-5 mu m.
The invention also provides a plant lateral root growth promoting regulator prepared by applying the compound, wherein the solvent of the regulator is dimethyl sulfoxide, and the concentration of the regulator is 10-500 nm. At high concentration (micromolar), the main root can be inhibited, and the growth of fibrous root can be promoted. At low concentrations (nanomolar), only fibrous root growth is promoted, with no effect on the primary root.
The invention also provides a preparation method of the compound capable of bidirectionally regulating plant growth, which comprises the following steps:
s01 synthesis of methylmalonic acid
Placing NaOH solution in a round-bottom flask, cooling to 0 ℃ at low temperature, adding diethyl methylmalonate, reacting at normal temperature for 60 hours after dropwise adding, and obtaining crude methylmalonic acid after reaction;
extracting the crude methylmalonic acid by diethyl ether to obtain an organic phase A and a water phase, and acidifying the water phase by 6mol/L HCl solution and extracting by ethyl acetate to obtain an organic phase B;
combining the organic phase A and the organic phase B, drying the mixture by anhydrous sodium sulfate, and performing rotary evaporation to dryness to obtain solid methylmalonic acid powder;
synthesis of S02, 3-methyl-5-hydroxyfuran-2 (5H) -one
At room temperature, adding water and glyoxal aqueous solution into a round-bottom flask, sequentially adding methylmalonic acid and 6mol/L HCl solution, heating to reflux, and reacting for 16H to obtain a crude product of 3-methyl-5-hydroxyfuran-2 (5H) -ketone;
adding NaCl solid into the obtained 3-methyl-5-hydroxyfuran-2 (5H) -ketone crude product to a saturated state, extracting by ethyl acetate to obtain an organic phase, drying the organic phase by anhydrous sodium sulfate, and then carrying out rotary evaporation to dryness to obtain solid powder;
redissolving the solid powder by using a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 5:2, and performing column chromatography to obtain a yellow solid, namely 3-methyl-5-hydroxyfuran-2 (5H) -ketone;
s03, synthesis of indole-3-carboxylic ester striga asiatica analogue
Adding indole-3-carboxylic acid, a 3-methyl-5-hydroxyfuran-2 (5H) -ketone 2a compound and a DMF solvent into a round-bottom flask, magnetically stirring for 10-15 minutes under an ice bath condition, adding thionyl chloride and catalytically metered triethylamine after stirring, heating to reflux, reacting for 8-12 hours, distilling to remove residual thionyl chloride after the reaction is finished, adding a proper amount of ethyl acetate into the reaction bottle to dissolve a distillation residue, washing with saturated saline solution, drying an ethyl acetate phase with anhydrous sodium sulfate, removing the solvent by using a rotary evaporator, and adding petroleum ether: and (3) performing column chromatography by using ethyl acetate as a developing agent with a ratio of 5:1 to obtain the indole-3-carboxylic ester striga asiatica analogs.
Preferably, in step S03, the magnetic stirring time is 10 minutes.
Preferably, the reaction time is 10 hours.
Compared with the prior art, the invention has the beneficial effects that:
the compound provided by the invention has a novel structure, is not recorded in the prior art, can be used for preparing a growth regulator for regulating the growth conditions of main roots and lateral roots of plants under the condition of different concentrations, and can be regulated in different growth processes of the plants, so that the growth of effective parts of the plants can be promoted.
Drawings
FIG. 1 is a physical diagram showing root growth of Arabidopsis thaliana plants treated for 6 days with 5. mu.M of the compound in the test example;
FIG. 2 is a physical diagram showing root growth of Arabidopsis thaliana plants treated with 5. mu.M compound for 12 days in the test examples;
FIG. 3 is a physical representation of root growth of Arabidopsis plants treated with DMSO for 6 days;
FIG. 4 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 5 is a physical map of root growth of Arabidopsis plants treated with 2uM compound for 6 days;
FIG. 6 is a physical map of root growth of Arabidopsis plants treated with 2uM compound for 12 days;
FIG. 7 is a physical map of root growth of Arabidopsis plants treated with DMSO for 6 days;
FIG. 8 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 9 is a physical representation of root growth of Arabidopsis plants treated for 5 days with 1 μ M compound;
FIG. 10 is a physical representation of root growth of Arabidopsis plants treated for 8 days with 1 μ M compound;
FIG. 11 is a physical map of root growth of Arabidopsis plants treated with 1 μ M compound for 12 days;
FIG. 12 is a physical map of root growth of Arabidopsis plants treated with DMSO for 5 days;
FIG. 13 is a physical map of root growth of Arabidopsis plants treated with DMSO for 8 days;
FIG. 14 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 15 is a pictorial representation of root growth of Arabidopsis plants treated for 5 days with 500nM compound;
FIG. 16 is a pictorial representation of root growth of Arabidopsis plants treated with 500nM compound for 8 days;
FIG. 17 is a pictorial representation of root growth of Arabidopsis plants treated for 12 days with 500nM compound;
FIG. 18 is a physical map of root growth of Arabidopsis plants treated with DMSO for 5 days;
FIG. 19 is a physical map of root growth of Arabidopsis plants treated with DMSO for 8 days;
FIG. 20 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 21 is a pictorial representation of root growth of Arabidopsis plants treated for 5 days with 100nM compound;
FIG. 22 is a pictorial representation of root growth of Arabidopsis plants treated for 8 days with 100nM compound;
FIG. 23 is a pictorial representation of root growth of Arabidopsis plants treated with 100nM compound for 12 days;
FIG. 24 is a physical map of root growth of Arabidopsis plants treated with DMSO for 5 days;
FIG. 25 is a pictorial representation of root growth of Arabidopsis plants treated with DMSO for 8 days;
FIG. 26 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 27 is a pictorial representation of root growth of Arabidopsis plants treated for 5 days with 10nM compound;
FIG. 28 is a pictorial representation of root growth of Arabidopsis plants treated with 10nM compound for 8 days;
FIG. 29 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days;
FIG. 30 is a physical map of root growth of Arabidopsis plants treated with DMSO for 5 days;
FIG. 31 is a physical map of root growth of Arabidopsis plants treated with DMSO for 8 days;
FIG. 32 is a physical map of root growth of Arabidopsis plants treated with DMSO for 12 days.
Detailed Description
Example 1
A compound for bidirectional regulation of plant growth, the compound having the formula (1):
the preparation method of the compound comprises the following steps:
s01 synthesis of methylmalonic acid
And (3) placing the NaOH solution into a round-bottom flask, cooling to 0 ℃ at low temperature, adding diethyl methylmalonate, reacting at normal temperature for 60 hours after dropwise addition is finished, and obtaining a crude product of the methylmalonic acid after the reaction is finished.
And (3) extracting the crude methylmalonic acid by diethyl ether to obtain an organic phase A and a water phase, and acidifying the water phase by 6mol/L HCl solution and extracting by ethyl acetate to obtain an organic phase B.
And combining the organic phase A and the organic phase B, drying the mixture by using anhydrous sodium sulfate, and performing rotary evaporation to dryness to obtain solid methylmalonic acid powder.
Synthesis of S02, 3-methyl-5-hydroxyfuran-2 (5H) -one
At room temperature, adding water and glyoxal aqueous solution into a round-bottom flask, then sequentially adding methylmalonic acid and 6mol/L HCl solution, heating to reflux, and reacting for 16H to obtain a crude product of 3-methyl-5-hydroxyfuran-2 (5H) -ketone.
Adding NaCl solid into the obtained crude product of the 3-methyl-5-hydroxyfuran-2 (5H) -ketone to a saturated state, extracting by ethyl acetate to obtain an organic phase, drying the organic phase by anhydrous sodium sulfate, and then carrying out rotary evaporation to dryness to obtain solid powder.
Redissolving the solid powder by using a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 5:2, and carrying out column chromatography to obtain a yellow solid, namely 3-methyl-5-hydroxyfuran-2 (5H) -ketone.
S03, synthesis of indole-3-carboxylic ester striga asiatica analogue
Adding indole-3-carboxylic acid, a 3-methyl-5-hydroxy furan-2 (5H) -ketone 2a compound and a DMF solvent into a round-bottom flask, magnetically stirring for 10 minutes under ice bath conditions, adding thionyl chloride and catalytically metered triethylamine after stirring is finished, heating to reflux, reacting for 10 hours, distilling to remove residual thionyl chloride after the reaction is finished, adding a proper amount of ethyl acetate into the reaction bottle to dissolve distillation residues, washing with saturated saline solution, drying the ethyl acetate phase with anhydrous sodium sulfate, removing the solvent by using a rotary evaporator, and using petroleum ether: and (3) performing column chromatography by using ethyl acetate as a developing agent with a ratio of 5:1 to obtain the indole-3-carboxylic ester striga asiatica analogs.
Test example 1
In the test example, root growth conditions of arabidopsis plants treated for 6 days and 12 days by applying 5 μ M compound in different growth periods are shown in fig. 1-2, and root growth conditions of arabidopsis plants treated for 6 days and 12 days by applying DMSO are shown in fig. 3-4.
The physical maps of the root growth conditions of arabidopsis plants treated for 6 days and 12 days by applying the 2uM compound are shown in figures 5-6, and the physical maps of the root growth conditions of arabidopsis plants treated for 6 days and 12 days by applying DMSO are shown in figures 7-8.
The real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying 1 mu M compound are shown in FIGS. 9-11, and the real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying DMSO are shown in FIGS. 12-14.
The real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying 500nM compound are shown in FIGS. 15-17, and the real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying DMSO are shown in FIGS. 18-20.
The real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying 100nM compound are shown in FIGS. 21-23, and the real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying DMSO are shown in FIGS. 24-26.
The real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying 10nM compound are shown in FIGS. 27-29, and the real graphs of the root growth of arabidopsis plants treated for 5 days, 8 days and 12 days by applying DMSO are shown in FIGS. 30-32.
Claims (6)
1. A compound capable of bidirectionally regulating plant growth, which is characterized by the structural general formula as shown in formula (1):
2. the regulator for inhibiting the main roots of plants and promoting the growth of the lateral roots of plants, which is prepared by applying the compound, is characterized in that a solvent is dimethyl sulfoxide, and the concentration is 1-5 mu m.
3. The regulator for promoting the growth of the lateral roots of the plants, which is prepared by applying the compound, is characterized in that a solvent is dimethyl sulfoxide, and the concentration is 10-500 nm.
4. A preparation method of a compound capable of bidirectionally regulating plant growth is characterized by comprising the following steps:
s01 synthesis of methylmalonic acid
Placing NaOH solution in a round-bottom flask, cooling to 0 ℃ at low temperature, adding diethyl methylmalonate, reacting at normal temperature for 60 hours after dropwise adding, and obtaining crude methylmalonic acid after reaction;
extracting the crude methylmalonic acid by diethyl ether to obtain an organic phase A and a water phase, and acidifying the water phase by 6mol/L HCl solution and extracting by ethyl acetate to obtain an organic phase B;
combining the organic phase A and the organic phase B, drying the mixture by anhydrous sodium sulfate, and performing rotary evaporation to dryness to obtain solid methylmalonic acid powder;
synthesis of S02, 3-methyl-5-hydroxyfuran-2 (5H) -one
At room temperature, adding water and glyoxal aqueous solution into a round-bottom flask, sequentially adding methylmalonic acid and 6mol/L HCl solution, heating to reflux, and reacting for 16H to obtain a crude product of 3-methyl-5-hydroxyfuran-2 (5H) -ketone;
adding NaCl solid into the obtained 3-methyl-5-hydroxyfuran-2 (5H) -ketone crude product to a saturated state, extracting by ethyl acetate to obtain an organic phase, drying the organic phase by anhydrous sodium sulfate, and then carrying out rotary evaporation to dryness to obtain solid powder;
redissolving the solid powder by using a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 5:2, and performing column chromatography to obtain a yellow solid, namely 3-methyl-5-hydroxyfuran-2 (5H) -ketone;
s03, synthesis of indole-3-carboxylic ester striga asiatica analogue
Adding indole-3-carboxylic acid, a 3-methyl-5-hydroxyfuran-2 (5H) -ketone 2a compound and a DMF solvent into a round-bottom flask, magnetically stirring for 10-15 minutes under an ice bath condition, adding thionyl chloride and catalytically metered triethylamine after stirring, heating to reflux, reacting for 8-12 hours, distilling to remove residual thionyl chloride after the reaction is finished, adding a proper amount of ethyl acetate into the reaction bottle to dissolve a distillation residue, washing with saturated saline solution, drying an ethyl acetate phase with anhydrous sodium sulfate, removing the solvent by using a rotary evaporator, and adding petroleum ether: and (3) performing column chromatography by using ethyl acetate as a developing agent with a ratio of 5:1 to obtain the indole-3-carboxylic ester striga asiatica analogs.
5. The method for preparing a compound capable of promoting germination of seed of parasitic plant based on indole-3-carboxylic acid as claimed in claim 4, wherein the magnetic stirring time is 10 minutes in step S03.
6. The method of claim 4, wherein the reaction time is 10 hours.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102906079A (en) * | 2010-03-31 | 2013-01-30 | 国立大学法人神户大学 | Germination-stimulant carbamate derivatives and process for preparation thereof |
| CN110734417A (en) * | 2018-07-20 | 2020-01-31 | 南开大学 | 2-butenolide acetamide compound and preparation method and application thereof |
| CN111533715A (en) * | 2020-04-22 | 2020-08-14 | 南京农业大学 | 2(5H) -furan-2-one derivative, preparation method thereof and application thereof in inhibiting rice tillering |
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2021
- 2021-01-25 CN CN202110095671.0A patent/CN112979622A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102906079A (en) * | 2010-03-31 | 2013-01-30 | 国立大学法人神户大学 | Germination-stimulant carbamate derivatives and process for preparation thereof |
| CN110734417A (en) * | 2018-07-20 | 2020-01-31 | 南开大学 | 2-butenolide acetamide compound and preparation method and application thereof |
| CN111533715A (en) * | 2020-04-22 | 2020-08-14 | 南京农业大学 | 2(5H) -furan-2-one derivative, preparation method thereof and application thereof in inhibiting rice tillering |
Non-Patent Citations (1)
| Title |
|---|
| J. C. MORRIS 等: ""Synthesis of highly enantio-enriched stereoisomers of hydroxy-GR24"", 《ORG. BIOMOL. CHEM.》, vol. 14, pages 1236 - 1238 * |
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