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Novel 1,2,4-triazole derivative of chitosan and preparation method thereof

A chitosan and triazole technology, applied in the field of marine chemical engineering, can solve problems such as limited application and gap, and achieve the effects of improving biological activity, overcoming poor solubility and good solubility

Active Publication Date: 2014-01-01
潍坊华诺生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the antibacterial activity of chitosan and chemical fungicides there is still a certain gap, thus limiting its application on crops

Method used

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  • Novel 1,2,4-triazole derivative of chitosan and preparation method thereof
  • Novel 1,2,4-triazole derivative of chitosan and preparation method thereof
  • Novel 1,2,4-triazole derivative of chitosan and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1 chitosan methyl 1,2, the preparation of 4-triazole derivative (1)

[0028] Add 1.30 grams of acetylthiourea chitosan with a molecular weight of 230,000 into a three-necked flask, add 20 mL of absolute ethanol, dropwise add 0.3 mL of acetic anhydride, heat to 60 ° C, and dropwise add hydrazine hydrate (1.0 mL) to it. 10 mL of ethanol solution, after the dropwise addition, the temperature was raised to reflux, and the reaction was carried out for 10 hours. The reactant was cooled to room temperature, filtered with suction, washed with absolute ethanol, and dried at 60° C. to obtain 0.70 g of white powder, namely chitosan methyl 1,2,4-triazole derivative.

[0029] The preparation of the acylthiourea chitosan can be found in the following documents: Zhimei Zhong, Ronge Xing, Song Liu, Lin Wang, Shengbao Cai, Pengcheng Li.Synthesis of acylthiourea derivatives of chitosan and their antimicrobial activities in vitro[J].Carbohydr Res, 2008, 343: 567-570.

[0030]...

Embodiment 2

[0031] Embodiment 2 chitosan chloromethyl 1,2, the preparation of 4-triazole derivative (2)

[0032] Add 4.41 grams of chloroacetylthiourea chitosan with a molecular weight of 230,000 into a three-necked flask, add 60 mL of absolute ethanol, dropwise add 0.9 mL of acetic anhydride, heat to 60 ° C, and dropwise add hydrazine hydrate (3.0 mL) 30 mL of ethanol solution, the temperature was raised to reflux after the dropwise addition, and the reaction was carried out for 10 hours. The reactant was cooled to room temperature, filtered with suction, washed with absolute ethanol, and dried at 60°C to obtain 3.30 g of yellow powder, namely chitosan chloromethyl 1,2,4-triazole derivative.

[0033] Infrared spectrum shows chitosan chloromethyl 1,2, the infrared spectrogram of 4-triazole derivative ( Figure 4 ) and the infrared spectrum of chloroacetylthiourea chitosan ( image 3 ) compared to that at 1258cm -1 The C=S absorption peak that appears becomes weaker obviously, and at th...

Embodiment 3

[0034] Embodiment 3 chitosan phenyl 1,2, the preparation of 4-triazole derivative (3)

[0035] Add 1.60 grams of benzoylthiourea chitosan with a molecular weight of 230,000 to a three-necked flask, add 20 mL of absolute ethanol, drop 0.3 mL of acetic anhydride, heat to 60 ° C, dropwise add hydrazine hydrate (1.0 mL ) of ethanol solution 10mL, the dropwise addition was completed and the temperature was raised to reflux, and the reaction was carried out for 10 hours. The reactant was cooled to room temperature, filtered with suction, washed with absolute ethanol, and dried at 60°C to obtain 1.0 g of white powder, namely chitosan phenyl 1,2,4-triazole derivative.

[0036] Infrared spectrum shows: the infrared spectrogram of chitosan phenyl 1,2,4-triazole derivative ( Figure 6 ) and the infrared spectrum of benzoylthiourea chitosan ( Figure 5 ) compared to that at 1261cm -1 The C=S absorption peak that appears becomes weaker obviously, and at the same time the 1656cm -1 The ...

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Abstract

The invention belongs to the technical field of ocean chemical engineering and especially relates to a novel 1,2,4-triazole derivative of chitosan and a preparation method thereof. The novel 1,2,4-triazole derivative of chitosan has a general formula I. In the general formula I, R represents alkyl, substituted alkyl or aryl and n is in a range of 4 to 4000. The novel 1,2,4-triazole derivative of chitosan has a chitosan structure introduced with 1,2,4-triazole groups and the 1,2,4-triazole groups and the chitosan structure have synergistic effects and thus a biological activity of chitosan is improved obviously and the novel 1,2,4-triazole derivative of chitosan has an effect of resisting plant pathogenic fungi.

Description

technical field [0001] The invention belongs to marine chemical engineering technology, in particular to a novel chitosan 1,2,4-triazole derivative and a preparation method thereof. Background technique [0002] Traditional chemical pesticides have good efficacy, but most of them have problems such as high toxicity, high residue, and severe resistance, which affect the sustainable development of agriculture and human health. Therefore, the development of new high-efficiency, low-toxicity, and environment-friendly biopesticides to replace some chemical pesticides is of great significance to the sustainable development of my country's agriculture and to ensure food safety. [0003] Chitosan is the only alkaline polysaccharide existing in nature. It is easy to biodegrade itself and has good biocompatibility. Studies have found that it has special functions such as sterilization, insecticide, and anti-pathogenic fungi. Seed germination has a good promotion effect. Chitosan and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
Inventor 李鹏程秦玉坤邢荣娥刘松于华华李克成孟祥涛崔金会李荣锋李冰
Owner 潍坊华诺生物科技有限公司
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