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New plant defence inducer 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester as well as preparation method and application thereof

A technology of crown ketone and inducer, which is applied in the field of pesticide chemistry, can solve the problems of poor solubility and limit the practical application of plant defense inducer activators, etc., and achieve the effect of good water solubility

Active Publication Date: 2013-05-22
SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this compound still has a significant defect in practical application, that is, its solubility in water is extremely poor when it is used as a plant defense inducer in the preparation of the corresponding aqueous solution, not only methanol or ethanol is needed to help dissolve, and the maximum concentration It can only reach 1mM, which severely limits its practical application as a plant defense induction activator

Method used

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  • New plant defence inducer 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester as well as preparation method and application thereof
  • New plant defence inducer 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester as well as preparation method and application thereof
  • New plant defence inducer 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Preparation of the compound crown ketone shown in formula (I)

[0024] Dissolve 0.41g of compound 6-ethyl-4-carboxy-indanone in 25ml of anhydrous dimethylformamide (DMF), and further add 0.31g of glycine methyl ester hydrochloride and 2,4,6-tris Pyridine, after stirring and mixing evenly, add 0.85g catalyst HATU step by step under the ice-water bath, continue to react at room temperature for 10 hours after stirring and reacting at 0°C for 2 hours, add 10ml saturated sodium bicarbonate solution and stir for 15 minutes after completion of the reaction, then use 3×10ml ether extraction, the ether extract was washed with 5ml of saturated brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure to obtain a light yellow solid, which was further washed with acetone and recrystallized to obtain 0.47g of the product (product 8) (yield 85%).

Embodiment 2

[0025] Embodiment 2: the identification of embodiment 1 product (product 8)

[0026] Light yellow solid, spectral analysis confirmed that the obtained compound is the target product molecule crown ketone shown in formula (I), chemical name: 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]- acetic acid methyl ester, the spectral data are as follows: 1 HNMR (500MHz, CDCl 3 )δ H:7.74(1H,s),7.72(1H,s),6.63(1H,bs,N-H),4.27(2H,d,J=5.0Hz,6-H),3.83(3H,s,-COOCH 3 ),3.38(2H,m,3-OCH 3 ),2.75(2H,q,J=7.5Hz,C H 2 CH 3 ),2.71(2H,m),1.28(3H,t,J=7.5Hz,CH 3 ); 13 C NMR (125MHz, CDCl 3 )δ C :206.5(CO),170.5(COOMe),167.2(CONH),151.6(C arom –C 2 h 5 ), 144.4 (C arom ), 138.6 (C arom ), 133.0 (C arom ), 132.3 (CH arom ),125.5(C arom ), 52.6 (OCH 3 ), 41.6 (CH 2 -NH),36.5(CH 2 -CO),28.4(CH 2 ),25.8(CH 2 ), 15.4 (CH 3 ); EI-MS m / z(rel.int.):275[M] + (40), 244(5), 187(30), 186(100), 158(24), 143(15), 115(13), 91(8).

Embodiment 3

[0027] Embodiment 3: the water solubility test analysis of the product corona tolin obtained in embodiment 1

[0028] Dissolve 11.0mg (about 0.04mM) of the product coronasin obtained in Example 1 in 0.15mL of methanol first, then add the solution dropwise into 10mL of distilled water being stirred with a magnetic stirrer to disperse and dissolve, and obtain a well-dispersed The clear aqueous solution of the embodiment 1 product coronetine of about 4mM concentration, illustrates that the solubility of this compound coronasin in water is greater than 4mM, and this shows that the clarified aqueous solution that can only prepare the maximum about 1mM concentration than reported compound coronetine better water solubility.

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Abstract

The invention provides a new plant defence inducer 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester as well as a preparation method and an application thereof. The structure of the 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester is shown in a formula (I) (described in the specification). The new compound 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester provided by the invention has good water solubility, and a low-concentration aqueous solution prepared from the compound shows strong induction activity the same as that of the reported compound coronalon in an induction analysis experiment test for multiple plant volatile components; and the induction analysis experiment test shows that the new compound is a plant defence inducer (or plant protective agent) with more advantageous characteristics and a popularization and practical prospect compared with the coronalon, and the 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester is hopeful to have a potential important application for carrying out environment-friendly plant protection or prevention and control of plant diseases and insect pests on crops or commercial crops.

Description

Technical field: [0001] The present invention belongs to the field of pesticide chemistry, and in particular relates to a new plant defense inducer crown 1, 2-[(6-ethyl-1-oxoindane-4-carbonyl)amio]-acetic acid methyl ester and its preparation method and its Use in the preparation of plant defense inducers or plant protection agents. Background technique: [0002] Frequent crop or economic crop pest disasters bring huge losses to the production of my country's agriculture, forestry and other industries every year. Exploring and developing more economical and effective new technology methods for plant pest control has always been a research topic that has attracted much attention. In terms of the control of plant diseases and insect pests, the most important means of prevention and control is the use of chemical pesticides. However, the long-term and large-scale use of chemical pesticides will not only cause serious pollution to the environment, but also bring direct or indir...

Claims

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Application Information

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IPC IPC(8): C07C235/84C07C231/02A01N37/46A01P21/00
Inventor 谭建文徐巧林王晶任慧郑梦斐
Owner SOUTH CHINA BOTANICAL GARDEN CHINESE ACADEMY OF SCI
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