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2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof

A technology of pyridinecarboylhydrazone and pyridinecarboylhydrazide, which is applied in the field of 2-hydroxy-1-naphthalene-3-pyridinecarboylhydrazone and its preparation, can solve the problems of unscreened herbicidal activity and low cost, and achieve the goal of preparing The method is simple, the cost is low, and the effect of high water solubility

Inactive Publication Date: 2011-07-20
LIAOCHENG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In-depth research on this type of compound is one of the hot spots in the pesticide industry today, which shows that this type of compound has broad development prospects, but a compound with high herbicidal activity, low cost, and suitable for large-scale production and use has not been screened so far.

Method used

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  • 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof
  • 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof
  • 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone and preparation method and applications thereof

Examples

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Embodiment

[0013] Example: Add 10mmol of 3-pyridinecarbohydrazide and 20-30ml of methanol to the flask, stir under reflux to dissolve the hydrazide completely, then add 10mmol of 2-hydroxyl-1-naphthaldehyde, and immediately a yellow precipitate is formed. React for 2-3 hours, cool to room temperature, and filter with suction to obtain the crude product of acylhydrazone. Recrystallize with a mixed solvent of absolute ethanol and DMF at a volume ratio of 1:1 to obtain yellow crystals. Then wash it with ethanol, dry it, put it in a vacuum desiccator and weigh it to a constant weight to get the pure product. Yield: 80%.

[0014] Through infrared spectrum analysis and NMR analysis, the results are as follows:

[0015] Infrared spectrum (KBr, cm -1 ): υ(OH), 3380, υ(C=O), 1701, υ(C=N), 1655.

[0016] 1 H NMR (d1-DMSO, ppm): δ7.63-9.17 (m, 4H, C 5 h 4 N-), 7.21-7.86 (m, 6H, C 10 h 6 -), 5.00 (s, 1H, -OH), 8.00 (s, 1H, -NH), 8.10 (s, 1H, CH=N). 13 C NMR (d1-DMSO, ppm): δ163.0 (C=O), 15...

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Abstract

The invention discloses 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone of which structural formula is shown as below. The preparation method comprises the following steps: adding 10mmol of 3-picolinyl hydrazide and 20-30ml of methanol in a flask, refluxing and stirring to ensure that the hydrazide is completely dissolved, then adding 10mmol of 2-hydroxyl-1-naphthoic aldehyde to generate yellow precipitate instantly, reacting for 2-3 hours, cooling to the room temperature, performing suction filtering to obtain a hydrazone crude product; and then using the mixed solvent of absolute alcohol of which volume is 1:1 and N, N-dimethylformamide to recrystalliza and obtain yellow crystals; then washing with ethanol, and drying to obtain the pure product. The 2-hydroxyl-1-naphthalene-3-pyridinecarbonylhydrazone has higher herbicidal activity and can be used to prepare a herbicide for killing Echinochloa crusgalli, Digitaria sanguinalis, radish and rape. The product of the invention is characterized by high herbicidal activity, good liposolubility, high water solubility, low cost, simple preparation method and the like and a new way is provided for the development of the herbicide.

Description

technical field [0001] The present invention relates to 2-hydroxy-1-naphthalene-3-pyridinecarboylhydrazone, its preparation method, and the application of the compound as a herbicide. Background technique [0002] Acylhydrazone compounds are products of nucleophilic addition of hydrazides to aldehydes or ketones followed by elimination of water loss. Due to the active groups such as Schiff base (-CH=N) and amide bond (-CONH-) in the molecular structure of acylhydrazone compounds, most of them have biological activities such as herbicide and sterilization. The acylhydrazone compounds have herbicidal activity and antibacterial activity, which have also been reported. In-depth research on this type of compound is one of the hot spots in the pesticide industry today, which shows that this type of compound has broad development prospects, but a compound with high herbicidal activity, low cost, and suitable for large-scale production and use has not been screened so far. . Con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/88A01N43/40A01P13/00
Inventor 尹汉东李静魏新庭
Owner LIAOCHENG UNIV
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