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Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria

A technology of trifluoromethylthiotryptanthrin and plant virus disease, which is applied in the direction of chemicals, biocides, and fungicides for biological control, and can solve problems such as by-products and low reaction yields

Active Publication Date: 2021-06-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction yields are moderate and by-products are formed

Method used

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  • Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria
  • Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria
  • Trifluoromethylthio-containing tryptamine derivative and preparation thereof, and application in prevention and treatment of plant viruses and pathogenic bacteria

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Embodiment 1: the synthesis of intermediate 1~24

[0055] 1: In a 100 mL three-necked flask, add methyltriphenylphosphine bromide (5.36 g, 15 mmol) and 20 mL of dry THF. Under the protection of argon, potassium tert-butoxide (1.68 g, 15 mmol) was added to the reaction flask in batches under ice-cooling, and after the addition was completed, the reaction was carried out at room temperature for 30 min. Then o-aminoacetophenone (1.21 g, 10 mmol) was added and reacted overnight. After the reaction was completed, saturated sodium bicarbonate was added, extracted with ethyl acetate, the extract was concentrated and then subjected to silica gel column chromatography to obtain the corresponding o-propenylaniline (0.88g, yield=74%). In a 100 mL one-necked flask, o-propenylaniline (0.99 g, 7.4 mmol) and triethylamine (1.53 g, 11.1 mmol) were dissolved in 15 mL of dichloromethane. Under ice-cooling, a solution of benzoyl chloride (1.0 mL, 8.9 mmol) in dichloromethane was slowly ...

Embodiment 2

[0080] Embodiment 2: Synthesis of tryptanthrin derivatives I-1~I-24

[0081] I-1: Take a 25mL Shrek tube, mix Intermediate 1 (0.0724g, 0.20mmol), AgSCF 3 (0.0502g, 0.24mmol), K 2 S 2 o 8 (0.0810g, 0.30mmol) and 2mL of DMSO were added, heated to 60°C, refluxed for 16h, and monitored by TLC. After the reaction was completed, the reaction solution was poured into water and extracted with ethyl acetate (3×10 mL). The organic phase was subjected to silica gel column chromatography (PE:EA=30:1) to obtain the target product I-1. White solid, 86% yield, mp: 97-98°C, 1 H NMR (400 MHz, CDCl 3 )δ8.62(d, J=8.0Hz, 1H), 8.43(d, J=7.9Hz, 1H), 7.79(d, J=3.7Hz, 2H), 7.57-7.45(m, 3H), 7.37( t, J=7.5Hz, 1H), 3.61(q, J=12.9Hz, 2H), 1.75(s, 3H). 13 C NMR (100MHz, CDCl 3)δ161.2, 159.8, 147.3, 139.3, 134.5, 133.1, 130.4 (q, J=307.8Hz), 129.6, 127.5, 127.2, 126.9, 126.8, 123.0, 121.6, 117.4, 48.7, 38.60 (q, J=2.0 Hz), 25.1.C 18 h 14 f 3 N 2 OS[M+H] + 363.0773, found (ESI + )363.0776. ...

Embodiment 3

[0107]Embodiment 3: the assay of anti-tobacco mosaic virus activity, assay procedure is as follows:

[0108] 1. Virus purification and concentration determination:

[0109] Virus purification and concentration determination were carried out in accordance with the SOP specification for tobacco mosaic virus compiled by the Bioassay Laboratory of the Institute of Elements, Nankai University. After the virus crude extract was centrifuged twice with polyethylene glycol, the concentration was measured, and it was refrigerated at 4°C for later use.

[0110] 2. Compound solution preparation:

[0111] After weighing, the original drug was dissolved in DMF to prepare 1×10 5 μg / mL mother solution, and then diluted with 1‰ Tween 80 aqueous solution to the required concentration; Ningnanmycin preparation was directly diluted with water.

[0112] 3. In vivo protection:

[0113] Select Shanxi tobacco with uniform growth at the 3-5 leaf stage, spray the whole plant, and repeat each treatm...

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PUM

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Abstract

The invention relates to a trifluoromethylthio-containing tryptamine derivative I and a preparation method thereof, and application of the trifluoromethylthio-containing tryptamine derivative I in prevention and treatment of plant viruses and pathogenic bacteria. According to the invention, the trifluoromethylthio-containing tryptamine derivative I shows anti-plant virus activity, wherein the inhibition rate of the derivative containing chlorine atoms in the structure on tobacco mosaic virus (TMV) can reach the level equivalent to that of virazole; and the compound also shows certain anti-plant pathogenic bacterium activity, and has relatively good inhibitory activity on physalospora piricola.

Description

technical field [0001] The invention relates to trifluoromethylthiotryptanthrin derivatives and their preparation and application in the prevention and treatment of plant virus and bacterial diseases, belonging to the technical field of agricultural protection. Background technique [0002] Tryptanthrin (Tryptanthrin) is a kind of indole quinazoline alkaloid (structural formula one), and its chemical name is indolo[2,1-b]quinazoline-6,12-dione (indolo[2 , 1-b]quinazoline-6,12-dione), a yellow needle-like crystal. It has two conformational isomers, the planar conformation α, which maximizes the aromatization and is the one with the lowest energy; the 11th position in the conformation β is an sp 3 The hybridized N atom is a chiral center, therefore, it may exist in two forms, R or S. However, since molecules usually exist in a planar state in solution, we cannot observe optical rotation. [0003] [0004] Tryptanthrin mainly exists in indigo-producing plants such as Poly...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01P1/00A01P3/00
CPCC07D487/04Y02A50/30
Inventor 汪清民郭金铖王兹稳刘玉秀宋红健李永强
Owner NANKAI UNIV
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