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Chromone-containing benzoyl hydrazone compound capable of suppressing growth of cyanobacteria

A technology for benzoyl hydrazones and compounds, which is applied in the field of chromone-containing benzoyl hydrazone compounds and their preparation, and can solve problems such as unfavorable fish production and fish death

Inactive Publication Date: 2012-11-07
HUAZHONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After the blue-green algae outbreak, the oxygen content in the water body is low, and fish will die in large areas, which is very unfavorable to fish production

Method used

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  • Chromone-containing benzoyl hydrazone compound capable of suppressing growth of cyanobacteria
  • Chromone-containing benzoyl hydrazone compound capable of suppressing growth of cyanobacteria
  • Chromone-containing benzoyl hydrazone compound capable of suppressing growth of cyanobacteria

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Compound I-1

[0014] Preparation of nitrogen'-[(4-oxo-4hydro-chromone-3-)methene]-3-bromobenzohydrazide

[0015]

[0016] Dissolve 1 mmol of 3-bromobenzoylhydrazide in 10 ml of absolute ethanol, add 1 mmol of 3-formylchromone, and stir at room temperature for 1 hour, a milky white turbidity is formed. Suction filtration, washing with ethanol, and drying of the filter cake yielded white powder nitrogen'-[(4-oxo-4hydro-chromone-3-)methene]-3-bromobenzohydrazide with a yield of 90%, m.p. 175-178°C.

[0017] Molecular formula: C 17 h 11 BrN 2 o 3 ;

[0018] 1 H NMR(600MHz,dmso)δ12.03(s,1H,NH),8.85(s,1H,2-H),8.63(s,1H,CH=N),8.21-7.39(m,8H,ArH) ;

[0019] HR-MS(ESI):m / z=371.0038, calcd for C 17 h 11 BrN 2 o 3 [M+H] + :371.0031.

[0020] Compounds 2-19 were all prepared in a similar manner to compound 1

[0021] Compound I-2

[0022] Preparation of nitrogen'-[(6-chloro-4-oxo-4hydro-chromone-3-)methene]-3-bromobenzohydrazide

[0023]

[0024] The obtain...

Embodiment 2

[0148] The growth inhibition test of Microcystis aeruginosa FACHB 912 was carried out on the 19 compounds synthesized above. Microcystis aeruginosa FACHB 912 was cultured in BG-11 (+N) liquid medium containing different concentrations of compounds in an artificial climate incubator. The temperature of the incubator is controlled at 28°C±1°C, the humidity is 60%, the light intensity is 6000lx, 12h (light): 12h (dark), vibration mode, and manual shaking 3 times a day.

[0149] The specific operation is as follows:

[0150] 1. Pre-cultivate a batch of cyanobacteria, after 4-7 days of growth to the logarithmic phase, measure OD680, and inoculate for use;

[0151] 2. Dilute the algae liquid in the logarithmic phase with fresh BG-11 (+N) medium to obtain the inoculum liquid, and control the algae cell concentration to about 1×10 6 a / mL;

[0152] 3. Weigh the compound in advance, dissolve it in DMSO, and prepare the compound with different concentrations. Add 200 μL of the dilute...

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Abstract

The invention discloses a chromone-containing benzoyl hydrazone compound capable of suppressing growth of cyanobacteria in a general formula I, synthesis of the compound and an in-vivo experiment on the benzoyl hydrazone for suppressing the growth of the cyanobacteria. In the formula, an R<1> represents hydrogen, halogen, C1-C4 alkyl groups or hydroxyl groups, an R<2>, an R<3> and an R<4> respectively represent hydrogen, halogen, hydroxyl groups or trifluoromethyl, and substituent groups represented by the R<2>, the R<3> and the R<4> can be identical or different. In the in-vivo experiment on the compound to microcystis aeruginosa FACHB912 which is the main type of cyanobacteria, a half maximal effective concentration value EC<50> of the compound ranges from 0.17muM to 33.37muM, and thus the compound has a remarkable effect for suppressing the growth of the cyanobacteria and can be used as an effective ingredient of an algicide.

Description

technical field [0001] The invention relates to a compound capable of inhibiting the growth of cyanobacteria and a preparation method thereof, in particular to a chromone-containing benzoylhydrazone compound capable of inhibiting the growth of cyanobacteria and a preparation method thereof. Background technique [0002] In recent years, with the mass production of human waste, the eutrophication of the water body has become more and more serious, and a large number of blue-green algae frequently broke out, which is also called the algae bloom phenomenon. After the death of cyanobacteria, algae toxins will be produced. Algae toxins are water-soluble and heat-resistant. Algae toxins in aqueous solution are not easily removed by boiling at high temperature. Coagulation precipitation, filtration, and chlorination in tap water treatment processes cannot remove them. Algae toxin is a kind of hepatotoxin, which is very toxic. It is a strong cancer-promoting agent for liver cancer a...

Claims

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Application Information

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IPC IPC(8): C07D311/22A01P1/00
Inventor 万坚涂其冬冯玲玲李定孙瑶王小风伊凡沙依巴木任彦亮程志刚
Owner HUAZHONG NORMAL UNIV
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