CN115353500B - Cinnamamide lactone compound with strigolactone activity and preparation and application thereof - Google Patents

Cinnamamide lactone compound with strigolactone activity and preparation and application thereof Download PDF

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CN115353500B
CN115353500B CN202211142420.4A CN202211142420A CN115353500B CN 115353500 B CN115353500 B CN 115353500B CN 202211142420 A CN202211142420 A CN 202211142420A CN 115353500 B CN115353500 B CN 115353500B
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strigolactone
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段留生
王春英
郭兵博
于春欣
姜峰
谭伟明
周于毅
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China Agricultural University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
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    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
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    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P21/00—Plant growth regulators
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

The invention discloses a cinnamamide lactone compound with strigolactone activity, and preparation and application thereof. The structural formula is shown in formula I. The invention provides a strigolactone analogue with simple structure, convenient synthesis and high biological activity, and meanwhile, the strigolactone analogue is subjected to the tests of seed germination of the orobanum seed, hypocotyl elongation and root growth of the arabidopsis thaliana and rice tillering, and the result shows that the strigolactone analogue has better seed germination activity on the orobanum seed and better inhibition activity on the hypocotyl elongation, lateral root growth and rice tillering of the arabidopsis thaliana. The compound is easy to prepare, low in cost, high in agricultural application popularization value, worthy of subsequent deep research and development, and is a plant growth regulator with wide application prospect.

Description

Cinnamamide lactone compound with strigolactone activity and preparation and application thereof
Technical Field
The invention belongs to the field of plant growth regulators, and particularly relates to a cinnamamide lactone compound with strigolactone activity, and preparation and application thereof.
Background
The plant growth regulator is widely used in agricultural production, can effectively regulate the growth process of crops, and achieves the purposes of stabilizing yield and increasing yield, improving quality, enhancing stress resistance of crops and the like. Strigolactones (SLs) are a new class of endogenous plant hormones of interest in recent years, and SLs are present in many plants, particularly in root secretions. The first SLs was a class of carotenoid terpenoid lactones small isolated from cotton root exudates in 1966A molecule. Strigolactone, which has been found in different plant species, is largely divided into two classes of compounds, typical and atypical, typical SL S By the bridge of butenolide ring (D ring) to tricyclic lactone (ABC ring) via enol ether, atypical SL S The ABC ring in (a) is replaced by an irregular ring structure.
As a class of naturally occurring plant signal molecules, strigolactone molecules of different structures may exhibit different biological activities. SL (SL) device S Regulating the coordinated development of root and overground part, such as branch branching/tillering and secondary growth of branch, and determining the density formation of primary root, lateral root, crown and adventitious root and root hair. Furthermore, SL S Also regulates leaf senescence and root nodulation, and is involved in pathogenic bacteria defense and abiotic stress response. SL (SL) device S As a rhizosphere signal molecule, the seed germination of the parasitic plant is induced, and a beneficial symbiotic relationship is established with the arbuscular mycorrhizal fungi by stimulating hyphal branching of the arbuscular mycorrhizal fungi.
Natural SL S The SLs analogue with high activity and simple structure is designed and synthesized as the current research hot spot. At present, the most widely used and effective analogue is GR24, but the complicated synthesis steps and low yield lead to high production cost, so that the large-scale popularization and use of the analogue are limited. Therefore, the strigolactone functional analogue with simple, cheap and reasonable design is important.
Disclosure of Invention
The invention aims to provide a cinnamamide lactone compound with strigolactone activity, and preparation and application thereof.
The structural formula of the cinnamamide lactone compound provided by the invention is shown as formula I:
in the formula I, the compound (I),
r represents a substituent on the benzene ring and can be selected from at least one of hydrogen, halogen, nitro, cyano, C1-C4 straight-chain or branched alkyl, C1-C4 alkoxy, C1-C4 alkyl substituted by halogen, acyl (concretely, formyl-CHO), aryl hetero group, heterocyclic group, carboxyl, aryl hetero group condensed with the benzene ring and heterocyclic group;
in the formula I, R is preferably at least one of hydrogen, 2-fluoro, 3-fluoro, 4-fluoro, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2-methyl, 3-methyl, 4-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 3, 4-dichloro, 2, 5-dichloro, H and 3, 4-methylenedioxy.
Specifically, the compound shown in the formula I is any one of the following compounds:
the invention also provides a preparation method of the compound shown in the formula I.
The preparation method of the compound shown in the formula I provided by the invention comprises the following steps:
allowing a compound shown in a formula II and a compound shown in a formula III to perform esterification condensation reaction in the presence of a condensation reagent to obtain a compound shown in a formula I;
r in formula II is the same as R in formula I;
the condensation reagent in the preparation method is at least one of DIC, DIEA, DCC, DMAP, EDCI and HOBt;
in the preparation method, the esterification condensation reaction is carried out at the temperature of-10 to 60 ℃, the preferable reaction temperature is room temperature, the reaction time can be 2 to 24 hours, and the preferable reaction time can be 12 hours, 4 to 8 hours and 8 to 12 hours;
the molar ratio of the compound shown in the formula II to the compound shown in the formula III can be 1:0.8-10, and can be 1:1.2-10.
In the above preparation method, the esterification condensation reaction is carried out in an organic solvent,
the organic solvent is at least one or any combination of two or more of cyclohexane, hexane, tetrahydrofuran, dichloromethane, 1, 4-dioxane, ethyl acetate, methanol, ethanol, n-propanol, carbon tetrachloride, DMF, chloroform, diethyl ether and acetonitrile;
in the invention, the compound shown in the formula II is prepared according to the following route:
r in the formulas (1) and (3) is the same as R in the formula I;
the preparation method comprises the following steps:
1) mixing substituted cinnamic acid shown in the formula (1) with glycine ethyl ester hydrochloride shown in the formula (2), hoBt, EDCI and triethylamine in an organic solvent, and reacting to obtain a compound shown in the formula (3);
2) Hydrolyzing the compound shown in the formula (3) in an organic solvent containing inorganic alkali, concentrating the mixture after the reaction is finished, adding the mixture into ice water, regulating the pH to 3-4 by using dilute hydrochloric acid, and carrying out suction filtration to obtain a filter cake, namely the compound shown in the formula (II);
in the step 1) of the method, the mol ratio of the substituted meat silicic acid to the glycine ethyl ester hydrochloride is 1:1-3,
the temperature of the reaction can be 20-30 ℃, and can be 25 ℃;
the organic solvent is one of dichloromethane, DMF and THF;
in the step 2), the hydrolysis temperature can be 0-30 ℃ and the hydrolysis time can be 2-16 h;
the inorganic alkali is one or more of sodium hydroxide, potassium hydroxide and lithium hydroxide;
the organic solvent is one or more of methanol, ethanol, chloroform, diethyl ether and acetonitrile.
In the present invention, the compounds of formula II I may be purchased directly or prepared as follows:
the preparation method comprises the following steps:
the compound shown in the formula (4) and the compound shown in the formula (5) are subjected to cyclization reaction under the catalysis of sulfuric acid in aqueous solution to obtain the compound shown in the formula III.
Wherein the molar ratio of the compound represented by the formula (4) to the compound represented by the formula (5) may be: 1:1.0-2.0;
the molar ratio of the compound of formula (4) to concentrated sulfuric acid may be: 1:0.01% -0.1%; the cyclization reaction time may be 12 to 24 hours.
The use of the compounds of the formula I described above as plant growth regulators is also within the scope of the invention:
1) Promoting germination of parasitic weed seeds;
2) Inhibiting the elongation of hypocotyl of plant seedling;
3) Promoting root hair growth of plants;
4) Inhibiting lateral root formation of plants;
5) Inhibiting branch development of the plant;
6) Promoting senescence of plant leaves;
7) Promote the growth of mycorrhizal fungi hyphae from mycorrhizal fungi.
The plant can be Arabidopsis thaliana, rice, wheat.
The parasitic weeds can be broomrape and strigola.
Specifically, the application is the application of the compound shown in the formula I in the following aspects:
1) Promoting broomrape seeds to germinate;
2) Inhibiting the elongation of the hypocotyl of the Arabidopsis thaliana, inhibiting the growth of main roots of the Arabidopsis thaliana and inhibiting the generation of lateral roots of the Arabidopsis thaliana;
3) Inhibiting rice tillering.
The invention also provides a plant growth regulator, which contains the compound shown in the formula I.
The invention provides a strigolactone analogue with simple structure, convenient synthesis and high biological activity, and meanwhile, the strigolactone analogue is subjected to the tests of seed germination of the orobanum seed, hypocotyl elongation and root growth of the arabidopsis thaliana and rice tillering, and the result shows that the strigolactone analogue has better seed germination activity on the orobanum seed and better inhibition activity on the hypocotyl elongation, lateral root growth and rice tillering of the arabidopsis thaliana. The compound is easy to prepare, low in cost, high in agricultural application popularization value, worthy of subsequent deep research and development, and is a plant growth regulator with wide application prospect.
Drawings
FIG. 1 is a synthetic scheme for the preparation of Compound II-04 in example 1 of the present invention.
Detailed Description
The following detailed description of the invention is provided in connection with the accompanying drawings that are presented to illustrate the invention and not to limit the scope thereof. The examples provided below are intended as guidelines for further modifications by one of ordinary skill in the art and are not to be construed as limiting the invention in any way.
The experimental methods in the following examples, unless otherwise specified, are conventional methods, and are carried out according to techniques or conditions described in the literature in the field or according to the product specifications. Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Example 1 preparation of Compound II-04
Compound II-04 was prepared according to the synthetic scheme shown in fig. 1.
The specific reaction steps are as follows:
methylmalonic acid (45.0 g) was added to a solution of glyoxal (79.8 g, 40% w/w solution) in water (400 mL) at room temperature, followed by 3mL of concentrated H 2 SO 4 Reflux-heating reaction, adding NaCl solid, extracting with ethyl acetate, and making the organic phase pass through anhydrous Na 2 SO 4 Drying, concentrating, and subjecting to column chromatography [ V (petroleum ether)) V (ethyl acetate) =5:2]5-hydroxy-3-methyl-2- (5H) -furanone was isolated as yellow solid 1 (21.3 g, 49%).
2 chloro-cinnamic acid (3.00 g,16.48 mmol), hoBt (3.34 g,24.72 mmol) and EDCI (4.76 g,24.82 mmol) were added to a 40mL dichloromethane solution, reacted at room temperature for 1.5h, a mixed system of glycine ethyl ester hydrochloride (3.45 g,24.72 mmol) and dichloromethane (50 mL) was added dropwise, followed by triethylamine to adjust the pH to neutrality and reaction at room temperature. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =3:1 ] and after 12h the reaction was completed. The reaction system was extracted with dichloromethane, and the organic phase was washed successively with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure, followed by separation by column chromatography to give white solid 2 (2.80 g, 63.61%).
The white solid 2 (2.00 g,7.49 mmol) obtained above was dissolved in 30 methanol, and a few drops of NaOH (6 mol/L) solution was added thereto for reaction at room temperature. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =1:1 ] and after 12h the reaction was completed. The reaction system was concentrated, and after adding a small amount of water, the pH was adjusted to 3-4 with 5% diluted hydrochloric acid, a white solid was precipitated, and the white solid 3 (1.60 g, 89.42%) was obtained by suction filtration and drying.
The white solid 3 (1.00 g,4.18 mmol), DCC (1.30 g,6.27 mmol) and DMAP (0.2 g,1.63 mmol) obtained above were added to THF (30 mL), and after 15 minutes of reaction, a solution of 5-hydroxy-3-methyl-2- (5H) -furanone (0.57 g,5.02 mmol) in THF was added dropwise to the reaction system and reacted overnight at room temperature. The reaction was monitored by thin layer chromatography [ TLC, V (petroleum ether): V (ethyl acetate) =1:1 ] and after 10h the reaction was complete. The reaction system was suction-filtered, the filtrate was extracted with dichloromethane and water, and the organic phase was washed successively with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and separated by column chromatography to give white solid II-04 (0.90 g, 64.21%).
Compounds II-01 to II-19 were synthesized according to the above-described schemes, the data for the physical chemistry of the compounds are shown in Table 1, and the NMR data for the typical compounds are shown in Table 2.
TABLE 1 appearance and yield of partial Compounds of formula I
Compounds of formula (I) R Yield is good Status of
II-01 2-F 51％ White solid
II-02 3-F 46％ White solid
II-03 4-F 53％ White solid
II-04 2-Cl 64％ White solid
II-05 3-Cl 66％ White solid
II-06 4-Cl 57％ White solid
II-07 2-Br 41％ White solid
II-08 3-Br 45％ White solid
II-09 4-Br 50％ White solid
II-10 2-CH 3 39％ White solid
II-11 3-CH 3 44％ White solid
II-12 4-CH 3 47％ White solid
II-13 2-OCH 3 42％ White solid
II-14 3-OCH 3 52％ White solid
II-15 4-OCH 3 48％ White solid
II-16 2,5-Cl 42％ White solid
II-17 3,4-Cl 43％ White solid
II-18 H 64％ White solid
II-19 3, 4-Methoxyene group 52％ White solid
TABLE 2 partial Compound Nuclear magnetic resonance data of formula I
Example 2, compounds of formula I were tested for germination activity in guarana seeds by the following procedure:
the seed of Guarana is soaked in 75% alcohol for 2min for surface sterilization, and then washed clean with sterile distilled water. A plastic petri dish with a diameter of 9cm was taken, two filter papers were laid on the bottom layer and wetted with sterile distilled water, and then a glass fiber filter paper sheet with a diameter of 10mm was laid on the bottom layer. The seeds were uniformly sprinkled on a wet glass fiber filter paper sheet, the number of seeds being about 30-80. The dishes were sealed with sealer and the seeds were pre-incubated in the dark at 25℃for 3-7 days. The glass fiber filter paper sheets of the precultured seeds are placed in a plastic culture dish, 50 mu L of the compound solution to be tested is added, and the culture dish is sealed by sealing glue. The seeds are placed into a constant temperature incubator at 25 ℃ for 7 days to be cultivated, a binocular microscope is adopted to observe and count the germination rate of the broomrape seeds, when radicle appears, the broomrape seeds are regarded as sprouting, commercial GR24 is used as a positive control, and sterile distilled water is used as a negative control. Each concentration compound was tested in triplicate, five experiments per concentration compound and mean and standard deviation calculated using GraphPadDose-response analysis was performed by Prism 8.0 software, results expressed as EC 50 (half maximal effect concentration) means that the EC of the compound is calculated 50 Values. The data on the germination activity of the compound of formula I on guarana is shown in table 3.
TABLE 3 Compound 10 of formula I -6 Induction germination Rate of Guarana seeds at M concentration
Compounds of formula (I) Germination rate (%) Compounds of formula (I) Germination rate (%)
GR24 92.2 II-10 25.9
II-01 35.6 II-11 25.0
II-02 44.1 II-12 12.1
II-03 47.9 II-13 39.0
II-04 42.5 II-14 14.6
II-05 81.6 II-15 29.7
II-06 90.7 II-16 36.2
II-07 68.3 II-17 25.4
II-08 53.8 II-18 39.4
II-09 23.9 II-19 30.1
As can be seen from Table 3, at 10 -6 At the drug concentration of M, all the compounds designed and synthesized have the effect of promoting the germination of the seed of the orobanche. Wherein, the compound II-06 has the best germination promoting activity on the seed of the orobanche, the germination rate reaches 90.7 percent, and the effect is equivalent to that of the control drug GR24 (92.2 percent); next is compound II-05 to81.6 percent and can also well promote the germination of the seed of the orobanche. The result shows that the novel compound has great potential in the application of parasitic weed seed germination agents under the same condition due to low cost of the compound.
Example 3, columbia wild type Arabidopsis thaliana hypocotyl elongation Activity test and root growth test
Wild type Arabidopsis seeds (Columbia-0, col-0) were sown in 1/2MS (0.8% agar, 1% sucrose and specified concentrations of compounds) with 1% sodium hypochlorite for 15min, washed with sterile water; the whole plant was subjected to vernalization at 4℃for 3 days in a refrigerator, then transferred to a climatic chamber in the dark, cultured at 22℃for 7 days, and after photographing, the hypocotyl length was measured by imageJ software. The formula is: hypocotyl elongation inhibition = (blank hypocotyl length-drug group hypocotyl length)/blank hypocotyl length x 100%, and the elongation inhibition of each compound and the control drug GR24 on the arabidopsis hypocotyl was calculated, and the test results of all compounds are shown in table 4.
The arabidopsis seeds are sterilized with 1% sodium hypochlorite solution for 15min, washed with sterile water and sown in 1/2MS medium (0.8% agar, 1% sucrose and specified concentration of compound); the leaf spring is spring-treated for 3 days in a refrigerator at 4 ℃, then transferred to a climatic chamber, cultured for 7 days in dark (16/8 h,22/19 ℃) and photographed as a whole, and the length of the main root of Arabidopsis is measured by Image J software, and the method comprises the following steps: main root growth inhibition ratio = (blank group main root length-drug group main root length)/blank group main root length×100%, main root growth inhibition ratio was calculated as shown in table 5; and the statistical root count was observed as shown in table 6.
TABLE 4 inhibition of Arabidopsis hypocotyl elongation at 10uM concentration of Compound of formula I
Compounds of formula (I) Inhibition ratio (%) Compounds of formula (I) Inhibition ratio (%)
GR24 36.9 II-10 18.6
II-01 1.6 II-11 6.8
II-02 -3.0 II-12 4.9
II-03 -1.7 II-13 -2.8
II-04 -2.5 II-14 -4.4
II-05 12.8 II-15 5.1
II-06 12.0 II-16 8.0
II-07 5.4 II-17 1.0
II-08 8.9 II-18 3.4
II-09 16.4 II-19 -7.1
From Table 4, it can be seen that the part of the cinnamamide lactone compounds related to the invention have a certain inhibition effect on the growth of the hypocotyl of Arabidopsis thaliana, wherein the inhibition effect of the compound II-10 is more obviously up to 18.6%, and the drug effect is possibly better along with the increase of the concentration.
TABLE 5 inhibition of Arabidopsis Main root growth at a partial Compound concentration of 10uM
Compounds of formula (I) Inhibition ratio (%) Compounds of formula (I) Inhibition ratio (%)
GR24 43.8 II-10 17.1
II-01 44.8 II-11 36.9
II-02 39.4 II-12 40.1
II-04 23.6 II-13 23.4
II-05 22.6 II-15 17.4
II-06 42.1 II-16 0.2
II-07 35.0 II-17 49.4
II-08 41.5 II-18 40.1
II-09 13.5 II-19 13.2
TABLE 6 rooting of Arabidopsis thaliana at 10uM concentration of partial compound of formula I and control drug treatment
Compounds of formula (I) Side root number (strip) Compounds of formula (I) Side root number (strip)
CK 1.9 II-10 0.7
GR24 0.3 II-11 1.5
II-01 1.0 II-12 0.5
II-02 0.2 II-13 1.1
II-04 1.3 II-15 1.1
II-05 1.4 II-16 1.1
II-06 0.3 II-17 1.4
II-07 0.6 II-18 0.9
II-08 0.8 II-19 0.8
II-09 0.3
As can be seen from tables 5 and 6, the cinnamamide analogues of the invention have similar functions to strigolactone, and have higher activity, and have better activity than GR24. As is clear from Table 5, at a concentration of 10. Mu.M, the growth inhibitory effect of a plurality of compounds on Arabidopsis main roots was comparable to that achieved by the same concentration of GR24, such as the compounds II-01, II-06, II-08, II-12, II-18, etc. The best activity for inhibiting the growth of the main root is the compound II-17, the inhibition rate reaches 49.4 percent, and compared with GR24, the inhibition effect is more obvious.
From Table 6, it can be seen that the compounds inhibit the primary root while the inhibition effect of most of the compounds on the lateral root production is apparent. Compound II-02 with the best inhibition effect, with the lateral root number of 0.2 and activity better than GR24 (0.3); and secondly, the compounds II-06 and II-09 have the inhibition effect equivalent to GR24. The compound has related activity of strigolactone, and has low cost and high utilization value under the same condition.
Example 4 inhibition of tillering in Rice by Compounds
Rice seeds (Nippon-Qing) were surface sterilized by washing with 1.5% sodium hypochlorite for 30 minutes, then thoroughly rinsing the seeds with sterile deionized water, and culturing in water at 30℃for 2 days in the dark. The pre-germinated seeds were transferred to filter paper in a 90mm dish and incubated with fluorescent white light (130-180 μm 2 s -1 ) Culturing at 30deg.C for 1 week, and 16 hr with light for 8 hr darkness. Seedlings 7 days old were transferred to a hydroponic box containing nutrient solution and grown in a climatic chamber. The rice was treated with the compound of formula I at a concentration of 2 μm using GR24 as a positive control. These compounds were administered twice a week for six total administrations. The tillering number per strain was measured at the final harvest and the test results for all compounds are shown in table 7.
TABLE 7 inhibitory Activity of Compounds of formula I against tillering in Rice
From the data in Table 7, it can be seen that the compounds prepared by the invention have various degrees of inhibition effects on rice tillering. Under the test concentration of 2uM, the compounds II-19 and II-13 have strong inhibition effect on the growth of rice tillering buds, the average tillering number is respectively 1.4 and 1.6, the activity is best, and the inhibition effect is obviously better than that of GR24 (2.6); and secondly, the average tiller number of the compounds II-04 and II-16 is 2.3. The compound has low cost and potential application value in agricultural production.
The present invention is described in detail above. It will be apparent to those skilled in the art that the present invention can be practiced in a wide range of equivalent parameters, concentrations, and conditions without departing from the spirit and scope of the invention and without undue experimentation. While the invention has been described with respect to specific embodiments, it will be appreciated that the invention may be further modified. In general, this application is intended to cover any variations, uses, or adaptations of the invention following, in general, the principles of the invention and including such departures from the present disclosure as come within known or customary practice within the art to which the invention pertains.

Claims (7)

1. A compound of formula I:
in the formula I, R is at least one of hydrogen, 2-fluoro, 3-fluoro, 4-fluoro, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2-methyl, 3-methyl, 4-methyl, 2-methoxy, 3-methoxy, 4-methoxy, 3, 4-dichloro, 2, 5-dichloro and 3, 4-methylenedioxy.
2. A process for preparing a compound of formula I in claim 1, comprising the steps of: allowing a compound shown in a formula II and a compound shown in a formula III to perform esterification condensation reaction in the presence of a condensation reagent to obtain a compound shown in a formula I;
formula II and formula III
R in formula II is the same as R in formula I.
3. The method according to claim 2, characterized in that: the condensing agent is at least one of DIC, DIEA, DCC, DMAP, EDCI and HOBt;
the esterification condensation reaction is carried out at the temperature of-10 to 60 ℃ for 2 to 24 hours;
the molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1:0.8-10.
4. The method according to claim 2, characterized in that: the esterification condensation reaction is carried out in an organic solvent,
the organic solvent is at least one or any combination of two or more of cyclohexane, hexane, tetrahydrofuran, dichloromethane, 1, 4-dioxane, ethyl acetate, methanol, ethanol, n-propanol, carbon tetrachloride, DMF, chloroform, diethyl ether and acetonitrile.
5. Use of a compound of formula I according to claim 1 as a plant growth regulator in the following aspects:
1) Promoting germination of parasitic weed seeds;
2) Inhibiting the elongation of hypocotyl of plant seedling;
3) Promoting root hair growth of plants;
4) Inhibiting lateral root formation of plants;
5) Inhibit the branching development of plants.
6. The use according to claim 5, characterized in that: the plant is Arabidopsis thaliana, rice and wheat;
the parasitic weeds are broomrape and strigola.
7. A plant growth regulator comprising a compound of formula I in claim 1.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012043813A1 (en) * 2010-09-30 2012-04-05 独立行政法人理化学研究所 Novel compound having strigolactone-like activity and use thereof
CN108912074A (en) * 2018-06-15 2018-11-30 清华大学 A kind of witchweed lactone derivatives of high activity and its preparation and application
CN114874165A (en) * 2022-06-20 2022-08-09 中国农业大学 Phenethyl ester vinyl ether lactone compound with strigolactone activity as well as preparation and application thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012043813A1 (en) * 2010-09-30 2012-04-05 独立行政法人理化学研究所 Novel compound having strigolactone-like activity and use thereof
CN108912074A (en) * 2018-06-15 2018-11-30 清华大学 A kind of witchweed lactone derivatives of high activity and its preparation and application
CN114874165A (en) * 2022-06-20 2022-08-09 中国农业大学 Phenethyl ester vinyl ether lactone compound with strigolactone activity as well as preparation and application thereof

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