Gramine derivative and preparation method and application thereof

A technology of anophylline and its derivatives, which is applied in the field of anophylline derivatives and its preparation, can solve the problems of high production cost, environmental pollution, low yield, etc., and achieve the effect of good anti-plant virus and germ activity

Active Publication Date: 2019-03-26
HEBEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The technical problem to be solved by the present invention is: provide anophylline derivative and its preparation method and application, wherein, described anophylline derivative is a brand-new anophylline derivative, and its preparation method overcomes the prior art The defects of low yield, high production cost and environmental pollution in the preparation of anophylline derivatives, the anophylline derivatives have good anti-plant virus and pathogen activity

Method used

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  • Gramine derivative and preparation method and application thereof
  • Gramine derivative and preparation method and application thereof
  • Gramine derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation method of the anophylline derivative shown in the chemical structural formula general formula I is as follows:

[0035] The prepared anophylline derivative shown in general formula I has the following chemical structural formula:

[0036]

[0037] In the general formula I of the above chemical structural formula, R 1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl or benzyl, R 2 phenyl, 2-fluorophenyl, 3-fluorophenyl, 3,4-difluorophenyl, 2,6-difluorophenyl, 2,4-difluorophenyl, 2,3-difluorobenzene Base, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2,4-dichlorophenyl, 2,3 -Dichlorophenyl, 2,5-dichlorophenyl, 4-chlorophenyl, 5-chloro-2-fluorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 4 -Iodophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-tri Fluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 3,5-bis(trifluo...

Embodiment 2

[0042] The preparation method of (N-((5-bromo-1-methyl-1H-indol-3-yl)(phenyl)methyl)pyridin-2-amine) shown in chemical structural formula I-1 is as follows:

[0043] The chemical structural formula I-1 of N-((5-bromo-1-methyl-1H-indol-3-yl)(phenyl)methyl)pyridin-2-amine is

[0044]

[0045] The concrete steps of its preparation method are as follows:

[0046] In the first step, at 0°C, add 0.64g or 16mmol of NaH into 10mL of DMF, stir and let it stand still, then suck out 5mL of the solvent DMF, then add 10mL of DMF, stand still after stirring and suck out 5mL of the solvent, and then Add 30-40 mL of DMF, 1.94 g (10 mmol) of 5-bromoindole, and 1.65 g (11.9 mmol) of iodomethane. After the addition is complete, move the mixture to room temperature for TLC detection. After the reaction is completed, slowly add water dropwise in an ice bath. Water phase with 30mL CH 2 Cl 2 Extract three times, wash the organic phase with water and saturated brine successively, combine the or...

Embodiment 3

[0049] The preparation method of (N-((5-bromo-1-methyl-1H-indol-3-yl) (4-fluorophenyl) methyl) pyridin-2-amine shown in chemical structural formula I-2 is as follows :

[0050] The chemical structural formula I-2 of N-((5-bromo-1-methyl-1H-indol-3-yl)(4-fluorophenyl)methyl)pyridin-2-amine is

[0051]

[0052] The concrete steps of its preparation method are as follows:

[0053] The first step, with embodiment 2;

[0054] In the second step, in an oil bath at 80°C, 0.376g or 4mmol of 2-aminopyridine, 0.496g or 4mmol of 4-fluorobenzaldehyde and 0.840g or 4mmol of the above-mentioned first step were added to the reactor under magnetic stirring conditions. After the addition of N-methyl-5-bromoindole, the system was controlled at 90°C and reacted for 3 hours. After the reaction was completed, 5mL of distilled water was added to the system for washing, and the washing was repeated three times. Chloromethane was extracted three times, the organic phases were combined, dried by...

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PUM

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Abstract

The invention relates to a gramine derivative and a preparation method and application thereof, in particular to a biocide containing a five-membered heterocyclic ring compound with one nitrogen atomused as the only heterocyclic atom. The gramine derivative has the following chemical structural general formula I as shown in the description. The preparation method of the gramine derivative has thespecific steps as shown in the following chemical reaction equation as shown in the description. The application of the gramine derivative is an agent for resisting plant virus and an agent for killing plant pathogenic fungi.

Description

technical field [0001] The technical scheme of the present invention relates to a biocide containing a five-membered ring heterocyclic compound with one nitrogen atom as the only ring heteroatom, in particular, a dianthine derivative and its preparation method and application. Background technique [0002] Phylloline is a natural alkaloid containing an indole skeleton. Its basic structural skeleton is a tertiary amine structure and an indole structure. Its chemical structural formula is as follows: [0003] [0004] Phylloline has extremely high biological activity. Widely distributed in nature, it is an allelopathic alkaloid produced by grasses such as wheat, barley and reed bamboo during the evolution process (Phytochemistry, 1984, 23(3), 539–541; Phytochemistry, 1985, 24(5),945–947; Exp.Appl.,1986,40(3),259–262.), has growth inhibitory effect on environmental plants, insects, microorganisms, etc. (Journal of Shaoyang University, 2003,2(2) , 131–135.). People use the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D401/14C07D409/14A01P1/00A01P3/00
CPCC07D401/12C07D401/14C07D409/14
Inventor 卢爱党杨珊王铁男李红岩汪清民
Owner HEBEI UNIV OF TECH
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