Condensation derivative of chitosan and substituted phenylthiosemicarbazide and preparation method thereof

A technology of thioanisidine and chitosan, which is applied in the field of marine chemical engineering, can solve problems such as the gap in antibacterial activity, and achieve the effects of improving biological activity, being easy to absorb, and overcoming poor solubility.

Active Publication Date: 2011-09-14
海臻(上海)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, the

Method used

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  • Condensation derivative of chitosan and substituted phenylthiosemicarbazide and preparation method thereof
  • Condensation derivative of chitosan and substituted phenylthiosemicarbazide and preparation method thereof
  • Condensation derivative of chitosan and substituted phenylthiosemicarbazide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of Derivative 1

[0039] 9.99 grams of acetylated chitosan with a molecular weight of 230,000 and 23.80 grams of o-toluidine thiourea were added to 300 mL of absolute ethanol, 2.5 mL of acetic acid was added dropwise to it under stirring, and the reaction was refluxed for 8 hours, cooled to room temperature, The reactant was suction-filtered, washed with absolute ethanol, and dried at 60°C to obtain an off-white powder, namely acetylated chitosan-o-toluenethiosemicarbazide, ie derivative 1, see Table 1 for the structural formula.

[0040] The preparation of described acetylated chitosan refers to the following documents:

[0041] 1. Fujii S, Kumagai H, Noda M. Preparation of poly(acy1) chitosans [J]. Carbohydr Res, 1980, 83(2): 389-393.

[0042] 2. Huang Liyao, Liu Chao. Preparation of hydrophobized long fatty chain acylated chitosan [J]. Journal of Huaqiao University (Natural Science Edition), 2005, 26(4): 439-441.

[0043] Infrared spectrum sho...

Embodiment 2

[0044] Example 2 Preparation of Derivative 2

[0045] 2.0 grams of acetylated chitosan with a molecular weight of 230,000 and 3.87 grams of o-chloroanilinothiourea were added to 100 mL of absolute ethanol, and 0.5 mL of acetic acid was added dropwise to it under stirring, and refluxed for 8 hours, cooled to room temperature, and reacted The product was suction filtered, washed with absolute ethanol, and dried at 60°C to obtain a yellow powder, which was acetylated chitosan condensed o-chlorophenylthiosemicarbazide, namely derivative 2. See Table 1 for the structural formula.

[0046] Infrared spectrum shows: the infrared spectrum of chitosan derivative 2 ( image 3 ) and the infrared spectrum of acetylated chitosan ( figure 1 ) compared to 3470.13, 3306.47, 3273.74cm -1 The absorption peak that appears is the characteristic absorption peak of NH, 1637.10cm -1 It is the characteristic absorption peak of C=N, 1529.98cm -1 It is the characteristic absorption of benzene ring, ...

Embodiment 3

[0047] Example 3 Preparation of Derivative 3

[0048] Add 1.0 g of acetylated chitosan with a molecular weight of 230,000 and 1.77 g of o-fluoroanilinothiourea to 50 mL of N,N-dimethylformamide, add 0.3 mL of acetic acid dropwise under stirring, and reflux for 10 hours , cooled to room temperature, the reactant was suction-filtered, washed with absolute ethanol, and dried at 60°C to obtain a yellow powder, namely acetylated chitosan condensed o-fluorophenylthiosemicarbazide, ie derivative 3, see Table 1 for the structural formula.

[0049] Infrared spectrum shows: the infrared spectrum of chitosan derivative 3 ( Figure 4 ) and the infrared spectrum of acetylated chitosan ( figure 1 ) compared at 3443.64, 3021.16cm -1 The absorption peak that appears is the characteristic absorption peak of NH, 1655.54cm -1 It is the characteristic absorption peak of C=N, 1539.50, 1515.70cm -1 It is the characteristic absorption of benzene ring, 1047.19cm -1 It is the characteristic absor...

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Abstract

The invention belongs to a marine chemical industry engineering technologies, and in particular relates to a novel condensation derivative of chitosan and substituted phenylthiosemicarbazide and a preparation method thereof. The invention provides a condensation derivative of chitosan and substituted phenylthiosemicarbazide, which has high water solubility, a novel structure and high bacteriostatic activity, and a preparation method thereof. The general formula of the novel condensation derivative of chitosan and substituted phenylthiosemicarbazide is shown as a formula I in the specification, wherein R1 is alkyl, halogen, trifluoromethyl or -NO2; R2 is -CH3, -CH2Cl or -Ar; and n=4-4000.

Description

technical field [0001] The invention belongs to marine chemical engineering technology, in particular to a novel chitosan-substituted thioanisemicarbazide derivative and a preparation method thereof. Background technique [0002] With the continuous reduction of cultivated land, the continuous increase of the world's population, and the continuous enhancement of human awareness of the protection of the living environment, population, food, and the environment have become current prominent issues and are placed in front of human beings. Although traditional chemical pesticides have made great contributions to controlling agricultural diseases and insect pests and increasing food production, most chemical pesticides have problems of high toxicity, high residue, and poor biocompatibility, which seriously affect the sustainable development of agriculture and human health. . Food safety and agricultural product export "green barriers" caused by excessive pesticide residues have ...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 李鹏程秦玉坤邢荣娥刘松李克成孟祥涛崔金会李荣锋李冰
Owner 海臻(上海)生物科技有限公司
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