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Banisterine benzoyl urea compounds and preparation method and application thereof

A technology for benzoyl urea and camel ketone, applied in the field of pesticides, can solve the problems such as the research and synthesis reports of benzoyl urea compounds of camel pine, and achieves simple structure, simple synthesis process and good inhibitory activity. Effect

Active Publication Date: 2015-05-20
SOUTH CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There are no reports on the research and synthesis of the benzoylurea compound of salaline

Method used

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  • Banisterine benzoyl urea compounds and preparation method and application thereof
  • Banisterine benzoyl urea compounds and preparation method and application thereof
  • Banisterine benzoyl urea compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of 1-methyl-β-carboline-3-ammonia (6a)

[0049] (Refer to literature method (Lin G.W., et al. Synthetic Communications , 2012, 42 , 1895-1910, namely reaction formula II).

[0050] 1. Step A: 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid ( 2 )Synthesis

[0051] Weigh 20.4g of L-tryptophan (0.1mol) into a three-necked flask equipped with an electric heating mantle and electric stirrer, add 70-80 mL of glacial acetic acid and 5mL of 40% acetaldehyde (0.12mol) under stirring, After stirring for 15 minutes, heat up to 80-100°C and react for 10 hours. TLC traces until the tryptophan disappears, stops heating, cools to room temperature and precipitates form, filters, and concentrates the filtrate under reduced pressure to remove excess acetic acid and water to obtain a large amount of shallow Brown flakes were washed with water to obtain a white product with a yield of 85%.

[0052] 2. Step B: methyl 1-methyl-1,2,3,4-tetrahydro-β-carbo...

Embodiment 2

[0060] Example 2: Synthesis of 1-phenyl-β-carboline-3-ammonia (7b)

[0061] Operation is the same as in Example 1, only in step A replace acetaldehyde with benzaldehyde. A yellow-green powder was finally obtained with a yield of 87%.

Embodiment 3

[0062] Example 3: Synthesis of 1-p-chlorophenyl-β-carboline-3-ammonia (7c)

[0063] Operation is the same as in Example 1, only in step A, acetaldehyde is replaced with p-chlorobenzaldehyde. Yellow-green flaky crystals were finally obtained with a yield of 79%.

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Abstract

The invention discloses banisterine benzoyl urea compounds and a preparation method and application thereof. The banisterine benzoyl urea compounds have a structural formula I shown in the specification; in the formula I, R1 can be methyl, phenyl, 3,4,5- triethoxy phenyl, p-methoxyphenyl or p-chlorphenyl, R2 can be H or Br, and X can be O or S. The banisterine benzoyl urea compounds have an outstanding insecticidal activity for Culex fatigans, prodenia litura and Chilo suppressalis; a part of the compounds are identical to a control insecticide Dibenzoyl-1-tert-butylhydrazine in term of activity; the banisterine benzoyl urea compounds have good inhibitory activity for rice sheath blight disease, alternaria solani, Collectotrichum musae, grey mould fruit rot of strawberry and sour rot pathogenic bacteria of citrus; a part of the compounds have better inhibitory activity for the above five phytopathogens than validamycin. The banisterine derivatives are simple in structure and easy to synthesize; the synthesis process is simple, the product purity is high; the banisterine benzoyl urea compounds and the preparation method thereof are suitable for large-scale industrial popularization and application.

Description

technical field [0001] The invention belongs to the technical field of pesticides. More specifically, it relates to a humaline benzoylurea compound and its preparation method and application. Background technique [0002] Camelina is a plant from Tribulus terrestris in my country ( Peganum harmala L . ), which is a kind of β-carboline alkaloid extracted and isolated from ), which has various biological activities such as anticancer, insecticidal, bacteriostatic and antiviral, and has attracted much attention from researchers at home and abroad. In recent years, the research on salicine mainly focuses on the anti-tumor aspect, and in-depth research has been carried out on structural modification, anti-tumor structure-activity relationship, and mechanism of action ((1) Pan Qichao, et al. cancer , 1985, 4 , 192-194; (2) Cao Jun, et al. cancer , 1993, 12 , 214-216; (3) Amy M.D., et al. Bioorganic & Medicinal Chemistry Letters , 2001, 11 , 1251-1255; (4) Cao R.H., et ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A01P7/04A01P3/00
CPCC07D471/04
Inventor 钟国华张智军胡美英曾勇
Owner SOUTH CHINA AGRI UNIV
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