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Application of nortopsentin alkaloids and derivatives thereof to prevention and treatment of plant diseases and insect pests

A technology for preventing and controlling pests and alkaloids, which is applied in the direction of chemicals, applications, and biocides for biological control. It can solve the problems of difficult synthesis, low natural content of Nortopsentin alkaloids, and insufficient research on biological activity. Good insecticidal activity, good anti-plant virus and fungus activity

Active Publication Date: 2019-03-05
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Due to the low natural content of Nortopsentin alkaloids and relatively difficult synthesis, the research on biological activity is not deep enough, mainly focusing on anticancer activity, and the research on antiviral and bactericidal aspects is still in its infancy. The application has not reported yet

Method used

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  • Application of nortopsentin alkaloids and derivatives thereof to prevention and treatment of plant diseases and insect pests
  • Application of nortopsentin alkaloids and derivatives thereof to prevention and treatment of plant diseases and insect pests
  • Application of nortopsentin alkaloids and derivatives thereof to prevention and treatment of plant diseases and insect pests

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: Synthesis of Nortopsentin alkaloid bisindole derivative structure Ia

[0031]

[0032] 18-1: Add indole (3.51g, 30mmol) and 150mL acetonitrile to a 500mL single-necked bottle in sequence, add 60% NaH (1.44g, 42mmol) under ice-cooling, stir for about 10min, add p-toluenesulfonyl chloride (6.27mmol) in batches g, 33mmol), after adding, return to room temperature reaction. The reaction was monitored by TLC, and the reaction was completed in about 4 hours. with saturated NH 4 The Cl solution was quenched, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and precipitated to obtain 8.06 g of a brown solid with a yield of 99% and a melting point of 76-78°C. 1 H NMR (400MHz, CDCl 3 ) δ7.99(d, J=8.4Hz, 1H), 7.76(d, J=8.4Hz, 2H), 7.56(d, J=3.6Hz, 1H), 7.52(d, J=7.6Hz, 1H) , 7.36-7.27(m, 1H), 7.24-7.18(m, 3H), 6.65(d, J=3.6Hz, 1H).

[0033] 18-2: The operation is the same as 18-1 to obtain a brown solid with a yield of 99% and a melting point ...

Embodiment 2

[0053] Embodiment 2: Synthesis of Nortopsentin alkaloid bisindole derivative structure Ib

[0054]

[0055] 25-1: Take a 250mL single-necked bottle, dissolve 70% NaSH (1.60g, 20mmol) in 20mL DMF, add MgCl 2 ·6H 2 O (2.03g, 10mmol), 3-cyanindole (1.42g, 10mmol) was added in batches under stirring, monitored by TLC, and stirred at room temperature for about 90min to complete the reaction. Pour the green suspension into 100 mL of water, filter with diatomaceous earth, add 1N HCl until no solid precipitates, add ethyl acetate for extraction, dry with anhydrous sodium sulfate, and obtain 1.57 g of yellow solid after precipitation, yield 89% , melting point: 141-142°C. 1 H NMR (400MHz, DMSO-d 6 )δ11.78(s, 1H), 8.96(s, 1H), 8.82(s, 1H), 8.71-8.54(m, 1H), 8.09(d, J=2.8Hz, 1H), 7.49-7.40(m , 1H), 7.21-7.09(m, 2H). 13 C NMR (100 MHz, DMSO-d 6 )δ193.6, 136.8, 128.0, 1259, 122.0, 121.8, 120.7, 116.3, 111.9.

[0056] 25-2: Same operation as 25-1, yellow solid, yield 87%, melting ...

Embodiment 3

[0065] Embodiment 3: Synthesis of Nortopsentin alkaloid bisindole derivative structure Ic

[0066]

[0067] 26-1: Add 2.34g (20mmol) indole and 80mL anhydrous ether to a 250mL round-bottomed flask, add a solution of oxalyl chloride (26mmol) in ether dropwise at 0°C, react at 0°C for about 1.5h, monitor by TLC, the reaction After completion, it was directly sucked and washed with ice anhydrous ether to obtain 3.65 g of yellow powder with a yield of 89%. No need to process, directly feed the next reaction.

[0068] 26-2: same operation as 26-1, brownish yellow powder, yield 87%,

[0069] 27-1: Add compound 26-1 (0.21g, 1mmol) into a 100mL single-necked bottle, add 10mL of anhydrous diethyl ether, add 2mL of concentrated ammonia water dropwise and stir at room temperature for 5min, monitor by TLC, the reaction of the raw materials is complete, filter with suction, wash with water, After washing with cold anhydrous ether, 0.16 g of a light yellow solid was obtained, with a yi...

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Abstract

The invention relates to the application of nortopsentin alkaloids and derivatives I thereof to resisting of plant viruses and pathogens and killing of insects. The nortopsentin alkaloids and the derivatives I thereof in the invention show particularly excellent activity against plant viruses, can effectively inhibit tobacco mosaic viruses (TMV), and also present excellent activity against plant pathogens and insecticidal activity. Substituents in a general formula as shown in the specification are defined in the specification.

Description

technical field [0001] The invention relates to the application of Nortopsentin alkaloids in the prevention and treatment of plant diseases and insect pests, and belongs to the technical field of agricultural protection. Background technique [0002] The ocean is a natural treasure house of human material resources. The total number of species of known marine organisms accounts for more than 80% of the earth's organisms (J Antibiot (Tokyo), 1994, 47, 1425-1433). More than 7,000 kinds of marine natural products have been isolated from sharks, corals and other marine organisms, and the newly discovered compounds are still increasing at an accelerated rate. Among the discovered compounds include terpenoids, polypeptides, steroids, polyethers, alkaloids, macrolides, polysaccharides and other compounds, about 50% have various biological activities, and more than 0.1% of the compounds have novel structures. It has remarkable activity and is very likely to be developed into a drug...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/50A01N43/78A01N43/76C07D401/14C07D413/14C07D417/14A01P1/00A01P3/00A01P7/02A01P7/04
CPCA01N43/50A01N43/76A01N43/78C07D401/14C07D413/14C07D417/14
Inventor 汪清民冀晓霏王兹稳刘玉秀
Owner NANKAI UNIV
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