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Compounding of (N-alkyl benzpyrole)-diketopiperazine compound and application of compound as plant growth regulator

A technology of diketopiperazine and hydrocarbyl indole, which is applied in the field of pesticides or applied organic chemistry, can solve problems such as unexplored plant growth regulation activity, and achieves the effects of cheap raw materials, easy operation, and simple post-synthesis treatment.

Inactive Publication Date: 2019-12-03
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no reports on the synthesis of such natural products and stereoisomers. In view of their structural similarity with Thaxtomin natural products, their plant growth regulating activity remains to be explored.

Method used

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  • Compounding of (N-alkyl benzpyrole)-diketopiperazine compound and application of compound as plant growth regulator
  • Compounding of (N-alkyl benzpyrole)-diketopiperazine compound and application of compound as plant growth regulator
  • Compounding of (N-alkyl benzpyrole)-diketopiperazine compound and application of compound as plant growth regulator

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of natural product indole-N-isopentenyl-tryptophan-valine diketopiperazine 5

[0032]

[0033] Taking the synthesis of target 5a as an example,

[0034] (1) Synthesis of compound 1a:

[0035] Weigh L-tryptophan (10g, 49mmol) into an eggplant-shaped bottle, add 100mL of dioxane to dissolve it, slowly add NaOH aqueous solution (2M, 40mL) in an ice bath, and then slowly add (Boc) 2 O (13.9g, 63.7mmol), the system naturally rises to room temperature, and thin-layer chromatography (TLC) tracks and monitors the reaction process, until the reaction is complete, the organic solvent is evaporated under reduced pressure, adjusted to pH 2-3 with dilute hydrochloric acid, and Dichloromethane extraction (50mL × 3), the combined organic phases were washed with water (40mL × 2) and saturated sodium chloride solution (40mL) successively, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain product 1a. 90%, used d...

Embodiment 2

[0062] Determination of the plant growth regulating activity of (N-alkylindole)-diketopiperazines.

[0063] The compounds involved in the above were formulated into series concentrations with 5‰DMSO or 10‰DMSO aqueous solution. Take a 24-well culture plate, spread double-layer filter paper in each well, add 300 μL of the prepared medicinal solution to each well with a pipette gun, and repeat each concentration three times, and use DMSO aqueous solution containing 5‰ as the control group, and the pre-germinated The processed seeds were taken out from the biochemical incubator and added to a 24-well cell culture plate, with 10 seeds per well, sealed with plastic wrap and covered, and placed in a light incubator for cultivation. After the seeds germinated, measure the Root length and shoot length are recorded, and the inhibition rate of root or shoot is calculated based on this.

[0064]

[0065] The plant growth regulating activities of representative (N-alkylindole)-diketop...

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PUM

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Abstract

The invention relates to compounding of a (N-alkyl benzpyrole)-diketopiperazine compound and application of the compound as a plant growth regulator. The chemical structural formula of the compound isshown as the general formula (I) and the general formula (II), wherein * in the general formula (I) and the general formula (II) represents chiral center, and spatial configuration is R or S; and R1and R2 represent substituent groups. For more details, please see the instruction.

Description

technical field [0001] The invention relates to the synthesis of a class of (N-hydrocarbylindole)-diketopiperazine compounds and their use as plant growth regulators, belonging to the field of pesticides or applied organic chemistry. Background technique [0002] The proportion of plant growth regulators in the pesticide industry is gradually increasing, and they have been widely used in modern agricultural production: for regulating the synthesis of nucleic acids, proteins and enzymes in plants; for rooting, germination, cell Elongation, organ differentiation, flowering, fruiting, defoliation, dormancy, etc. play a regulatory role. At present, the use of plant growth regulators has become an important means to increase crop yield and improve the quality of agricultural products. Currently common plant regulators include indole acetic acid, indole butyric acid, gibberellin, ethylene, kinetin, zeatin, naphthalene acetic acid, abscisic acid, phenoxyacetic acid compounds and b...

Claims

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Application Information

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IPC IPC(8): C07D403/06C07D487/04A01N43/60A01N43/90A01P21/00
CPCA01N43/60A01N43/90C07D403/06C07D487/04Y02P20/55
Inventor 李圣坤崔鹏程臧传丽
Owner NANJING AGRICULTURAL UNIVERSITY
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