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Alkaloid streptindole derivative, preparation thereof, and application of alkaloid streptindole derivative in prevention and control of plant viruses and pathogenic bacteria

A technology for plant pathogens and derivatives, which is applied in the fields of chemicals for biological control, botanical equipment and methods, applications, etc., and can solve the problems of few therapeutic agents and few plant virus inhibitors.

Active Publication Date: 2021-06-29
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, not only are there not many effective plant virus inhibitors, but also there are fewer therapeutic agents, and the control effects of the reported agents are mostly below 60% when they are actually applied in the field.
At present, there is no report about the activity of this type of compound against plant virus pathogens

Method used

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  • Alkaloid streptindole derivative, preparation thereof, and application of alkaloid streptindole derivative in prevention and control of plant viruses and pathogenic bacteria
  • Alkaloid streptindole derivative, preparation thereof, and application of alkaloid streptindole derivative in prevention and control of plant viruses and pathogenic bacteria
  • Alkaloid streptindole derivative, preparation thereof, and application of alkaloid streptindole derivative in prevention and control of plant viruses and pathogenic bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of N-(2,2-bis(1H-indol-3-yl)ethyl) pivalamide (I-1):

[0023] The first step: 0 ℃, under stirring state, add I 2 (0.13 g, 0.5 mmol). Keep stirring at this temperature for 30min, add 5% Na 2 S 2 o 3 solution (20 mL) to quench the reaction. The reaction solution was extracted with ethyl acetate (3×50mL), the organic phase was washed with saturated brine (100mL), anhydrous Na 2 SO 4 Dry, filter and concentrate. The residue was subjected to column chromatography with petroleum ether and ethyl acetate (2:1, v / v) to obtain a pink solid compound 2-(2,2-bis(1H-indol-3-yl)ethyl)isoindoline - 1,3-Dione (3) (0.97 g, 96%). Melting point 210-211°C; 1 H NMR (400MHz, CDCl 3 )δ7.97(s, 2H, NH), 7.75(d, J=8.0Hz, 2H, Ar-H), 7.72(dd, J=3.2, 5.5Hz, 2H, Ar-H), 7.61(dd, J=3.0, 5.4Hz, 2H, Ar-H), 7.29(d, J=8.0Hz, 2H, Ar-H), 7.13(t, J=7.2Hz, 2H, Ar-H), 7.09(d, J=2.0Hz, 2H, Ar-H), 7.03(t, J=7.5Hz, 2H, Ar-H), 5.31(t, J=7.7Hz, 1H, Ar 2 -CH), 4.37 (d, J=7.8Hz, 2H, C...

Embodiment 2

[0026] Embodiment 2: the synthesis of alkaloid streptindole derivatives I-2~I-11:

[0027] 0°C, under stirring, the corresponding isothiocyanate (3.64 mmol) was slowly added to a solution of compound 4 (1 g, 3.64 mmol) in dichloromethane (50 mL), and the reaction solution naturally rose to room temperature, and reacted for 3 h. Slowly add water (40 mL) to the reaction system dropwise to quench the reaction, separate the layers, extract the aqueous phase with dichloromethane (30 mL×2), combine the organic phases with saturated sodium bicarbonate solution (40 mL), saturated saline solution (40 mL ) washing, anhydrous Na 2 SO 4 Drying, suction filtration, concentration, and column chromatography yielded compounds I-2 to I-11;

[0028] 1-(2,2-bis(1H-indol-3-yl)ethyl)-3-phenylthiourea (I-2). Yellow-brown solid; yield 70%; melting point 214-215°C; 1 H NMR (400MHz, CDCl 3 )δ8.00(s, 2H, NH), 7.64(d, J=8.0Hz, 2H, Ar-H), 7.36(t, J=8.4Hz, 4H, Ar-H), 7.29(d, J= 7.0Hz, 1H, Ar-H), 7.18...

Embodiment 3

[0038] Embodiment 3: the synthesis of alkaloid streptindole derivatives I-12~I-19:

[0039] The first step: 0 ℃, under stirring state, add I 2 (0.13 g, 0.5 mmol). Keep stirring at this temperature for 30min, add 5% Na 2 S 2 o 3 solution (20 mL) to quench the reaction. The reaction solution was extracted with ethyl acetate (3×50mL), the organic phase was washed with saturated brine (100mL), anhydrous Na 2 SO 4 Dry, filter and concentrate. The residue was subjected to column chromatography with petroleum ether and ethyl acetate (5:1, v / v) to obtain brown oily compound 6 (1.45 g, 91%), 1 H NMR (400MHz, CDCl 3 )δ8.03(s, 2H, NH), 7.67(d, J=7.9Hz, 2H, Ar-H), 7.30 (t, J=8.1Hz, 2H, Ar-H), 7.23-7.21(m, 2H, Ar-H), 7.14-7.10(m, 2H, Ar-H), 7.00(d, J=2.0Hz, 2H, Ar-H), 5.53(s, 1H, Ar 2 -CH), 4.25(q, J=7.1Hz, 2H, CH 2 ), 1.29(t, J=7.1Hz, 3H, CH 3 ); 13 C NMR (100MHz, CDCl 3 )δ173.7, 136.3, 126.7, 123.5, 122.1, 119.5, 119.3, 113.5, 111.3, 61.2, 40.7, 14.3.

[0040] Step 2: Add ...

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Abstract

The invention relates to an alkaloid streptindole derivative, a preparation method thereof, and an application of the alkaloid streptindole derivative in control of plant virus and pathogen diseases. It is found that the streptindole derivatives I-1 to I-19 show good anti-plant virus and pathogen activity for the first time, and can well inhibit 14 plant pathogens including tobacco mosaic virus (TMV), cucumber fusarium wilt, peanut brown spot, apple ring spot, wheat sheath blight, corn microblotch, watermelon anthracnose, fusarium moniliforme, tomato early blight, wheat gibberellic disease, rice blast, phytophthora capsici, sclerotium of rape, cucumber gray mold and rice sheath blight.

Description

technical field [0001] The invention relates to an alkaloid streptindole derivative and its preparation and application in preventing and treating plant viruses and bacterial diseases, belonging to the technical field of agricultural protection. Background technique [0002] Plant virus disease, also known as "plant cancer", is a serious disease next to fungal damage in agricultural production. Due to the special structure, physiology and biochemistry of plant viruses, humans have not yet found an anti-plant virus agent with high efficiency and low toxicity. Therefore, the area of ​​plant virus diseases is constantly expanding, which seriously affects the increase of farmers' income and benefits. Improve (Science., 2014, 344(6181): 299-303). Tobacco mosaic virus (Tobacco Mosaic Virus, TMV) is currently the most in-depth research model virus in the world, belonging to Togaviridae (Togaviridae) single-stranded RNA (ssRNA) virus (Annu. . Phytopathol., 2004, 42(1): 13-34). TM...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C07D405/14C07D209/18C07D209/14A01N43/38A01N47/30A01N47/32A01N47/28A01P1/00A01P3/00
CPCA01N43/38A01N47/30A01N47/32A01N47/28C07D409/14C07D405/14C07D209/18C07D209/14Y02A50/30
Inventor 王兹稳高咏悦康锦
Owner TIANJIN NORMAL UNIVERSITY
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