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Oleanolic acid oxime ester derivate, preparation method and application thereof

A technology of oxime ester and esterification reaction, applied in the field of oleanolic acid oxime ester derivatives and its preparation and application, to achieve the effects of cheap raw materials, good growth inhibition, and simple reaction route

Inactive Publication Date: 2012-09-26
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only preliminary studies on medicine at home and abroad, but no reports on pesticides.

Method used

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  • Oleanolic acid oxime ester derivate, preparation method and application thereof
  • Oleanolic acid oxime ester derivate, preparation method and application thereof
  • Oleanolic acid oxime ester derivate, preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0035] Preparation of oleanolic acid oxime protected by benzylation

[0036]

[0037] Add 40g of oleanolic acid and 25g of anhydrous potassium carbonate to a 500mL round bottom flask, dissolve with about 300mL of DMF, and add 16mL of BnBr dropwise. Then react at room temperature for 4h. The system was filtered, the filtrate was washed with water, extracted with dichloromethane, separated, the organic phase was dried and concentrated to obtain 46 g of a white solid. The obtained product was dissolved in anhydrous dichloromethane, 25g of PDC and 25mL of acetic anhydride were added, and heated to reflux for 3h. Precipitate under reduced pressure, dissolve with ethyl acetate, filter with diatomaceous earth layer, concentrate the filtrate to obtain 44g of solid, dissolve with 300mL of dry pyridine, add 53g of hydroxylamine hydrochloride, react at 80°C for 30min, precipitate under reduced pressure, dichloromethane Extraction, washing with water, liquid separation, drying of the...

Embodiment 1

[0038] Example 1. Preparation and structure identification of compound CAU2012-A-01 (R=4-Cl-phenyl).

[0039]

[0040] In a 100mL round-bottomed flask were added benzylated-protected oleanolic acid oxime (2g, 3.5mmol), 4-Cl-benzoic acid (0.66g, 4.2mmol) and DCC (N,N'-dicyclohexylcarbodi imine) (1g, 5mmol), dissolved in 30mL of anhydrous dichloromethane, heated to reflux for 4h, cooled to room temperature after the reaction, filtered, washed with dichloromethane, the filtrate was precipitated under reduced pressure, separated by column chromatography to obtain a white powder solid. The obtained solid was dissolved in an appropriate amount of methanol, 0.8 g of Pd / C was added, and stirred at room temperature under hydrogen for 12 hours. After the reaction was completed, the Pd / C was removed by filtration, and the filtrate was precipitated under reduced pressure. 01, weight 1.8g. The two-step yield was 83%. m.p.98-100.

[0041] The structural confirmation data are as follo...

Embodiment 2

[0044] Embodiment 2, the preparation of compound CAU2012-A-01 emulsifiable concentrate

[0045] Add 1~10g of compound CAU2012-A-01, 5~15g of emulsifier, and 0.1~1g of penetrant into a 100mL volumetric flask, and then use solvents such as toluene, xylene, etc. to dilute to obtain an emulsifiable concentrate with a content of 1~10%.

[0046] Other emulsifiable concentrates of compounds with the general formula CAU2012-A can be prepared according to the above method.

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Abstract

The invention discloses an oleanolic acid oxime ester derivate compound, a preparation method and an application thereof. The structural formula of the compound is shown in formula I, and in the formula I, R refers to furyl, pyridyl, 1-menaphthyl, 4-chlorophenoxy methyl or phenyl with 1 to 2 substitutional groups; and the substitutional groups in phenyl with 1 to 2 substitutional groups are halogen (such as fluorine, chlorine, bromine and iodine) or nitryl. The preparation method comprises the following steps: 1) performing the esterification reaction between oleanolic oxime subject to benzylation protection and substituted carboxylic acids to prepare an oxime ester compound; and 2) removing benzylation protection on the oxime ester compound by Pd / C-H2 to prepare the compound in the formula I. The bactericidal activity test result shows that CAU2012-A has a favorable effect of inhibiting growth of sclerotinia scleotiorum, phytophthora melongenae, botrytis cintrea, pyricularia grisea, rhizoctonia solani and cotton fusarium wilt.

Description

technical field [0001] The invention relates to an oleanolic acid oxime ester derivative, a preparation method and application thereof. Background technique [0002] As a substance unique to fungal cell walls and insect cuticles, chitin does not exist in mammals and plants. Any substance that can interfere with chitin biosynthesis or deposition will affect fungi and insects. Glucosamine-6-phosphate synthase is the key enzyme system in the first step of chitin biosynthesis, which catalyzes the formation of D-glucosamine-6-phosphate from D-fructose-6-phosphate and L-glutamine and L-glutamic acid reaction. For fungi and bacteria, the loss of D-acetylglucosamine-6-phosphate caused by the inactivation or inhibition of glucosamine-6-phosphate synthase is fatal, and for insects, it will seriously affect its several functions. Butin synthesis, but relatively safe for mammals. Due to the unique safety and high selectivity of glucosamine-6-phosphate synthase, the exploration of inh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A01N47/38A01N47/18A01N37/50A01N43/40A01N43/08A01N37/34A01N25/02A01N25/14A01P3/00
Inventor 张建军赵汗青郑鹭飞梁晓梅金淑惠王道全
Owner CHINA AGRI UNIV
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