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High-activity benzoiso abscisic acid analogue and preparation method thereof

A high-activity, benzoisotropic technology, applied in botany equipment and methods, oxidative preparation of carboxylic acids, ozone oxidation preparation of carboxylic acids, etc., can solve the problems of 8'-hydroxyabscisic acid instability and low ring-closing activity

Inactive Publication Date: 2013-12-11
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, abscisic acid is easily metabolized and inactivated in plants to generate 8'-hydroxyabscisic acid, which is very unstable. It undergoes an intramolecular Michael addition reaction under the catalysis of cyclase, and the ring-closing activity is very high. Low Runner Bean Acid

Method used

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  • High-activity benzoiso abscisic acid analogue and preparation method thereof
  • High-activity benzoiso abscisic acid analogue and preparation method thereof
  • High-activity benzoiso abscisic acid analogue and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Embodiment 1: the synthesis of compound (II)

[0014] Step 1: Preparation of 2,2-dimethyl-3,4-dihydronaphthalene-1(2H)-one

[0015] Add NaH (11.6g, 0.34mol, 70%), tetralone (10.0g, 0.69mol) and 150mL anhydrous tetrahydrofuran into a dry 250mL three-necked flask, and stir at room temperature for 10 minutes to obtain a gray suspension. Then methyl iodide (11.1 mL, 178 mmol) was added dropwise to the above suspension, heated to 40° C. for 30 minutes after the dropwise addition, and then continued to stir at room temperature for 3 hours. After the reaction was completed, a small amount of water was slowly added dropwise to quench, extracted with ethyl acetate (3×20mL), the organic phases were combined, washed three times with saturated brine, dried over anhydrous magnesium sulfate, filtered, concentrated, and the concentrate was directly chromatographed (petroleum Ether: ethyl acetate = 10:1) to obtain 2,2-dimethyl-3,4-dihydronaphthalene-1(2H)-one (11.3, 95%) as a yellow o...

Embodiment 2

[0024] Example 2: Biological Activity of Benzoabscisic Acid Analogs

[0025] 1. Arabidopsis Seed Germination and Seedling Growth

[0026] Sample preparation: Preparation of (±)-ABA and test agent solution: Accurately weigh a certain amount of (±)-ABA and test agent, dissolve them in 1mL of anhydrous methanol respectively to obtain a 10mM mother solution, and store at -20°C light save. Pipette a certain amount of mother liquor with a pipette gun and dilute to the desired concentration with distilled water.

[0027] MS Medium (100 mL): Dissolve 0.44 g of MS519, 3.0 g of sucrose and 0.9 g of agar in 100 mL of distilled water.

[0028] When preparing the medium, first dissolve MS and sucrose in distilled water, and use KOH (2N) to adjust the pH value of the solution to 5.8-6.0. Divide into 75mL bottles, then accurately weigh 0.67g of agar and add to each bottle, cover with a parafilm and fix it with a rubber band. Put it into a high-temperature sterilization pot and sterilize ...

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Abstract

The invention provides a novel abscisic acid type synthetic plant hormone benzoiso abscisic acid (II) which has good abscisic acid type plant growth adjustment activity in a raceme form or in a single optical living form, wherein the activity of the R-body (compound II-a) is superior to the natural abscisic acid. The novel abscisic acid type synthetic plant hormone benzoiso abscisic acid can be used in the agriculture production as the abscisic acid type synthetic plant hormone.

Description

technical field [0001] The invention relates to a synthesis method and application of a class of benzisoabscisic acid analogs with high biological activity. Background technique [0002] Abscisic acid (I) is a phytohormone widely present in plants. It was first isolated from cotton bolls by Ohkuma in 1963. It forms with plant abscission, induces dormancy, inhibits germination, promotes organ aging and shedding, and enhances stress resistance Sex and so on are closely related, known as "plant stress resistance factor". [0003] However, abscisic acid is easily metabolized and inactivated in plants to generate 8'-hydroxyabscisic acid, which is very unstable. It undergoes an intramolecular Michael addition reaction under the catalysis of cyclase, and the ring-closing activity is very high. Low in ranunculus acid. [0004] [0005] In order to overcome this defect, a series of anti-metabolite analogs of abscisic acid have been designed and synthesized, but unfortunately onl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/90C07C51/36C07C51/16A01N37/42A01P21/00
Inventor 覃兆海韩小强万川肖玉梅
Owner CHINA AGRI UNIV
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