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Harmine compound and applications of harmine compound in prevention and control of peronophthora litchi chen disease

A technology of humaline and compounds, applied in the application field of pesticide fungicide drugs, to achieve the effects of small molecular weight, inhibitory effect, and inhibited growth

Active Publication Date: 2015-11-11
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are very few research reports on the application of camel alkaloid compounds as pesticides in the control of plant diseases. The research reports on Phytophthora, Citrus Sour Rot and Banana Fusarium wilt, but the compounds of camel alkaloids have not yet penetrated into the actual production application

Method used

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  • Harmine compound and applications of harmine compound in prevention and control of peronophthora litchi chen disease
  • Harmine compound and applications of harmine compound in prevention and control of peronophthora litchi chen disease
  • Harmine compound and applications of harmine compound in prevention and control of peronophthora litchi chen disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1 N-ethyl-1-phenyl-β-carboline-3-carboxamide (F1)

[0031] 1. Step A: Synthesis of 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2)

[0032] Weigh 20.4g L-tryptophan (0.1mol) into a three-necked flask equipped with an electric heating mantle and an electric stirrer, add 100mL glacial acetic acid while stirring, and add 12.25g benzaldehyde (0.12mol) at the same time. After stirring at room temperature for 15 minutes, the temperature is increased. Reacted at 80~100℃ for 10h, TLC traced to the disappearance of tryptophan, stopped heating, cooled to room temperature and precipitated, filtered, and the filtrate was concentrated under reduced pressure to remove excess acetic acid and water to obtain a large amount of light brown flakes. After washing with water, a white product, namely 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid was obtained with a yield of 85%.

[0033] 2. Step B: Synthesis of 1-phenyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic ...

Embodiment 2

[0043] Example 2N,N-Diethyl-1-phenyl-β-carboline-3-carboxamide (F2)

[0044] 1. The operation is the same as in Example 1, except that in step E, diethylamine is used instead of ethylamine.

[0045] 2. The product monitoring data are as follows: Yield: 57.10%; Melting point: 210-212°C; IR (KBr) cm -1 :3449(ν N-H ),2918,2851(ν C-H ),1623(ν C=O ),1022(ν C-N ); 1 H-NMR(600MHz,DMSO)δ11.71(1H,s,N(9)H,c), 8.42(1H,s,C(4)H,c), 8.35(1H,d,J=7.8Hz ,C(5)H,c),8.02(2H,d,J=7.4Hz,Ph(2,6)H),7.67(1H,d,J=8.2Hz,C(8)H,c), 7.63(2H,t,J=7.6Hz,Ph(3,5)H),7.56(2H,m,J=19.5,7.5Hz,C(7)H,c,Ph(4)H),7.29( 1H, t, J = 7.4 Hz, C (6) H, c), 3.50 (4H, m, J = 13.7, 6.8 Hz, CH 2 ),1.23-1.18(6H,m,CH 3 ).

Embodiment 3

[0046] Example 3 N-isopropyl-1-phenyl-β-carboline-3-carboxamide (F3)

[0047] 1. The operation is the same as in Example 1, except that in step E, isopropylamine is used instead of ethylamine.

[0048] 2. The product monitoring data are as follows: Yield: 47.27%; Melting point: 188-191°C; IR (KBr) cm -1 :3430(ν N-H ),2924,2850CH,CH 3 ,1647(ν C=O ),1252(ν C-N ); 1 H-NMR(600MHz,DMSO)δ11.82(1H,s,N(9)H,c),8.82(1H,s,C(4)H,c),8.41(1H,d,J=7.9Hz ,CO-NH), 8.28(1H,d,J=8.3Hz,C(5)H,c),8.12(2H,d,J=7.3Hz,Ph(2,6)H),7.67(3H, dd,J=17.0,8.1Hz,C(8)H,c,Ph(3,5)H),7.59(2H,dd,J=17.0,7.7Hz,C(7)H,c,Ph(4 )H),7.35-7.23(1H,m,C(6)H,c), 4.20(1H,m,J=13.4,6.7Hz,CH), 1.26(6H,d,J=6.6Hz,CH 3 ).

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Abstract

The present invention discloses a harmine compound, wherein the chemical structure formula is represented by a formula (I), R1 is selected from phenyl, p-nitrophenyl, p-methoxyphenyl, 3,4,5-trimethoxyphenyl, p-trifluoromethylphenyl and p-chlorophenyl, R2 is selected from ethyl, isopropyl, 2-pyridyl and 2-chlorophenyl, and R3 is selected from hydrogen and ethyl. According to the present invention, the compound provides good inhibition effects on multiple pathogenic bacteria, especially provides good inhibition and prevention and control effects on peronophthora litchi chen, has advantages of small molecular weight, simple structure, easy synthesis and the like, can effectively inhibit hypha growth, sporangium production and sporangium germination of peronophthora litchi chen, has good potential in prevention and control of peronophthora litchi chen disease, and is expected to become a new pesticide fungicide, such that the small molecule compound of the present invention can be used as the new pesticide for prevention and control of the peronophthora litchi chen disease so as to be developed and can provide the new way and means for prevention and control of the peronophthora litchi chen disease.

Description

Technical field [0001] The invention belongs to the technical field of application of pesticide bactericide drugs. More specifically, it relates to a harmine compound and its application in preventing and treating litchi downy phytophthora. Background technique [0002] Litchi Downy Phytophthora is a very serious disease that occurs on litchi. The pathogen is a fungus called PeronophthoralitchiChen, which was first discovered in Taiwan in 1934 (ChenCC..SpecialPublicCollegeAgriculture, Natl.TaiwanUniversity, 1961,10:1-37.). The pathogenic fungus can cause great harm from the extraction of flower spikes to fruit maturity and even post-harvest storage and transportation. It can harm the inflorescence, fruiting twigs, young fruits, and stalks, and can also harm nearly mature fruits. The diseased spots quickly expanded to the whole fruit, causing the whole fruit to change color and fall off, causing a large number of fruit drops, which seriously affected the yield. Young leaves can...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01N43/90A01P3/00
CPCA01N43/90C07D471/04
Inventor 翁群芳李志斌张智军钟国华罗建军张耀谋
Owner SOUTH CHINA AGRI UNIV
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