Application of Alkaloid Streptindole and Its Derivatives in Controlling Plant Virus Bacterial Diseases

A technology of derivatives and alkaloids, applied in the field of agricultural protection, can solve the problems of few plant virus inhibitors and few therapeutic agents.

Active Publication Date: 2021-12-10
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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  • Application of Alkaloid Streptindole and Its Derivatives in Controlling Plant Virus Bacterial Diseases
  • Application of Alkaloid Streptindole and Its Derivatives in Controlling Plant Virus Bacterial Diseases
  • Application of Alkaloid Streptindole and Its Derivatives in Controlling Plant Virus Bacterial Diseases

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of Compounds I-1~I-3: 0°C, under stirring, add the corresponding indole 1 (5mmol) and aldehyde 2 (0.26 g, 2.5mmol) to the acetonitrile solution (25mL) 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 compounds I-1~I-3.

[0023] Ethyl 2,2-bis(1H-indol-3-yl)acetate (I-1). Brown oil; yield 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 )δ...

Embodiment 2

[0026]Example 2: Synthesis of 2,2-bis(1H-indol-3-yl)acetohydrazide (I-4): under stirring, dissolve ester I-1 (1.59g, 5mmol) in ethanol solution ( 25 mL) was added with 80% hydrazine hydrate (25 mL). Reflux for 3 hours, cool to room temperature, concentrate part of the ethanol, precipitate a large amount of solid, suction filter, wash with water, and dry to obtain white solid compound I-4 (1.26g, 83%), melting point 234-235°C; 1 H NMR (400MHz, DMSO-d 6 ): δ10.87(s, 2H, NH), 9.42(s, 1H, NH 2 -NH), 7.57(d, J=7.9Hz, 2H, Ar-H), 7.34(d, J=8.1Hz, 2H, Ar-H), 7.17(d, J=2.2Hz, 2H, Ar-H ), 7.07-7.03(m, 2H, Ar-H), 6.96-6.92(m, 2H, Ar-H), 5.26(s, 1H, Ar-H 2 -CH), 4.26(s, 2H, NH-NH 2 ); 13 C NMR (100MHz, DMSO-d 6 )δ172.3, 136.6, 127.1, 124.1, 121.3, 119.4, 118.6, 114.3, 111.8, 39.5.

Embodiment 3

[0027] Embodiment 3: Compound 2,2-bis(1H-indol-3-yl)ethanol (I-5) and 2,2-bis(1H-indol-3-yl)ethyl acetate (I- 6) Synthesis of:

[0028] Step 1: Slowly add lithium aluminum tetrahydride (0.57g, 15mmol) to tetrahydrofuran (50mL) under stirring at 0°C, stir for 10min, then slowly add ester I-1 (1.59g, 5mmol), the reaction solution naturally Rise to room temperature, react for 3 h, and slowly drop water (10 mL) into the reaction system to quench the reaction. Add diatomaceous earth for suction filtration, wash the filter cake with ethyl acetate, combine the organic phases with anhydrous Na 2 SO 4 Drying, suction filtration, concentration, and column chromatography gave light yellow oily compound I-5 (1.02 g, 74%); 1 H NMR (400MHz, CDCl 3 )δ7.95(s, 2H, NH), 7.60(d, J=7.9Hz, 2H, Ar-H), 7.17-7.20(m, 4H, Ar-H), 7.09(t, J=6.2Hz, 2H, Ar-H), 6.72(s, 2H, Ar-H), 4.72(t, J=5.9Hz, 1H, Ar 2 -CH), 4.20 (d, J=5.8Hz, 2H, CH 2 ), 2.32(s, 1H, OH); 13 C NMR (100MHz, CDCl 3 )δ136.5, 126.9, ...

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Abstract

The present invention relates to the application of a kind of alkaloid streptindole and its derivatives in the treatment of plant virus pathogenic bacteria, the present invention finds for the first time that streptindole and its derivatives I‑1~I‑14 show very good activity against plant virus pathogens, can Very good at inhibiting tobacco mosaic virus (TMV) and cucumber blight, peanut brown spot, apple ring pattern, wheat sheath blight, corn small spot, watermelon anthrax, rice banished seedlings, tomato early blight, wheat gibberella, rice blast, Phytophthora capsici, sclerotia of rapeseed, gray mold of cucumber, sheath blight of rice 14 kinds of plant pathogens.

Description

technical field [0001] The invention relates to the application of alkaloid streptindole and its derivatives in the prevention and treatment of 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. There are more than 1,000 common plant virus diseases, most of which are caused by 716 viruses. Since the plant virus is a living parasite, after it invades the host cell, the viral nucleic acid will bind to the ribosome of the host, and the viral protein will be replicated during the metabolism of the host. Therefore, it is still very difficult at this stage to find a drug that does not cause damage to the host and can effectively inhibit the virus (Chinese Science: Chemistry, 2016, 46 (11): 1204-1209; Chinese Tobacco Science, 2011 , 32(1):84-91.). In the early 1980s, the losses caus...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A01N43/38A01N47/30A01P1/00A01P3/00C07D209/18C07D209/14C07D209/12C07D209/48C07D209/10
CPCA01N43/38A01N47/30C07D209/18C07D209/14C07D209/12C07D209/48C07D209/10
Inventor 王兹稳高咏悦张铭君
Owner TIANJIN NORMAL UNIVERSITY
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