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Synthesis of novel 3-seleno indole with vegetation promotion and selenium enriching functions

A selenium generation and compound technology, applied in the direction of plant growth regulators, plant growth regulators, botanical equipment and methods, etc., can solve the problems of not being able to increase agricultural production, limiting the scope of application, and lacking some functions

Inactive Publication Date: 2008-02-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because exogenous indoleacetic acid is easily degraded by plants, external application of indoleacetic acid cannot be an effective means of increasing agricultural production
Indoleacetic acid analogs such as 2,4-dichlorophenoxyacetic acid and naphthaleneoxyacetic acid are often used in agricultural production as plant growth regulators, but these compounds lack part of the function of indoleacetic acid as a plant messenger, which limits their application range

Method used

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  • Synthesis of novel 3-seleno indole with vegetation promotion and selenium enriching functions
  • Synthesis of novel 3-seleno indole with vegetation promotion and selenium enriching functions
  • Synthesis of novel 3-seleno indole with vegetation promotion and selenium enriching functions

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Example 1: Synthesis of 3-diselenyl-1-hydrogen-indole (compound 1)

[0062]

[0063] Dissolve 2 grams (30 mmol) of malononitrile in 5 ml of DMF, add 6.7 grams (60 mmol) of selenium dioxide in batches under vigorous stirring, and absorb the released gas with 5% NaOH solution. (22.5mmol) DMF (5ml) solution of indole, after the dropwise addition, stir at room temperature until the disappearance of indole, about 3 hours. The reaction solution was poured into ice water and kept stirring, a yellow solid precipitated, suction filtered, the solid was taken and dried, and recrystallized from toluene to obtain 3.9 g of the product, the yield was 78%, the melting point was 75-79°C, GC / MS: 222, 196, 169, 42, 117, 89.

Embodiment 2

[0064] Embodiment 2: Synthesis of 3-diselenyl-1-hydrogen-indole (compound 2)

[0065]

[0066] (2) Weigh 2.22 grams (10 mmol) of the product synthesized in step (1), add it to 10 ml of absolute ethanol, add 0.2 grams (5 mmol) of NaOH in 1 ml of aqueous solution dropwise under N protection conditions, stir at room temperature for 30 minutes, then add 10 ml of water Hydrolysis, extraction twice with 20 ml of ether, drying of the organic phase over anhydrous magnesium sulfate, rotary evaporation under reduced pressure to obtain 1.6 g of the product with a yield of 82%.

[0067] Melting point 122-124°C; 1 H NMR (CDCl 3)δ (ppm): 7.47 (d, J=8.1, 2H, indole-CH), 7.44 (d, J=8.0, 2H, indole-CH), 7.29 (s, 2H, indole-CH), 7.18(t, 2H, indole-CH), 7.06(t, 2H, indole-CH); IR(KBr): 3339, 2956, 1477, 1444, 1401, 1099cm -1 ; HR-MS: C 16 h 13 N 2 Se 2 (M+H) + Calculated value: 392.9409; Tested value: 392.9394.

Embodiment 3

[0068] Embodiment 3: Synthesis of selenium-acetate ethyl-3-selenium-indole (compound 3)

[0069]

[0070] Weigh 0.392 g (1 mmol) of compound 2, dissolve it in 5 ml of ethanol, and stir under nitrogen protection. Add 0.41 g NaBH in batches 4 , stirred for about 30 minutes, the solution changed from yellow to colorless, and a solution of 0.117 g of ethyl bromoacetate in 5 ml of ethanol was added dropwise. TLC detects that the reaction is complete. Spin to remove ethanol. Add 10ml ethyl acetate to dissolve and wash twice with water. The organic phase was taken, dried, concentrated and then subjected to silica gel column chromatography to obtain the product.

[0071] The melting point is 65-66°C.

[0072] 1 H NMR (CDCl 3 )6 (ppm) 7.62 (d, 1H, J=7.65, indole-H), 7.52 (s, 1H, indole-H), 7.45 (d, 1H, J=4.99, indole-H), 7.18 -7.10(m, 2H, indole-H), 3.95(s, 2H, -CH 2 -), 3.36 (m, 2H, -CH 2 -), 2.87(t, 3H, -CH 3 ).

[0073] IR (KBr): 3263, 2918, 1707, 1410, 1257, 1080cm ...

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Abstract

The invention discloses the structure, the preparation process and the usage of a novel 3-substituted indole compound .The invention is characterized in that carbon 3-position of the indole is introduced with the selenium and is then connected with other substituents, which improves the stronger plant growth regulating function relative to the indole acetic acid. The compound of the invention can also be taken as an enriched selenium agent of the plant.

Description

technical field [0001] The invention relates to the structure of a novel 3-selenoindole compound and its application in regulating plant growth and enriching selenium. Background technique [0002] Indole acetic acid is the earliest plant auxin discovered. It participates in the regulation and control of many physiological and biochemical processes in plants. Such as cell elongation and growth, cambium cell division, vascular tissue differentiation, leaf and flower shedding, Top dominance, tropism, rooting and transport of assimilates, etc. Because exogenous indoleacetic acid is easily degraded by plants, external application of indoleacetic acid cannot be an effective means of increasing agricultural production. Indoleacetic acid analogs such as 2,4-dichlorophenoxyacetic acid and naphthaleneoxyacetic acid are often used in agricultural production as plant growth regulators, but these compounds lack part of the function of indoleacetic acid as a plant messenger, which limit...

Claims

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Application Information

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IPC IPC(8): C07D209/04A01N43/38A01P21/00
Inventor 李忠钱旭红马严明黄青春宋恭华
Owner EAST CHINA UNIV OF SCI & TECH
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