Chitosan oligosaccharide Schiff base phosphonate as well as preparation method and application thereof

A technology of Schiff base phosphonate and chitosan oligosaccharides, applied in the field of development and utilization of biological resource pesticides, to achieve the effects of easy control of temperature conditions, significant induction of disease resistance, and good resistance to tobacco mosaic virus activity

Inactive Publication Date: 2012-07-04
HENAN AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] On the other hand, Schiff bases and Schiff base metal complexes are also a class of compounds with a wide range of biological activities. There have been many reports on their bactericidal and antiviral activities.

Method used

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  • Chitosan oligosaccharide Schiff base phosphonate as well as preparation method and application thereof
  • Chitosan oligosaccharide Schiff base phosphonate as well as preparation method and application thereof
  • Chitosan oligosaccharide Schiff base phosphonate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Preparation of 5-chlorosalicylaldehyde chitooligosaccharide Schiff base phosphonate

[0042] (1) Preparation of salicylaldehyde chitooligosaccharide Schiff base

[0043] After soaking and swelling 7.0186g of chitosan oligosaccharide in 20mL of absolute ethanol solvent, 8.0538g of salicylaldehyde and 0.2445g of NaOH were added (to adjust the pH value of the solution to 7.5-9), and microwave heating was performed under reflux for 1.5h. After the reaction, the product was dried by suction filtration, and the product was extracted with ethanol for 24 hours to remove excess salicylaldehyde and substituted salicylaldehyde in the product, and the product was vacuum-dried at a temperature lower than 50°C. Yield 4.2815g.

[0044] (2) Preparation of 5-chlorosalicylaldehyde chitooligosaccharide Schiff base phosphonate (S-COS-P)

[0045] 1.8339 g of the salicylaldehyde chitooligosaccharide Schiff base (S-COS) prepared in the above step (1) was reacted with 2.2766 g of d...

Embodiment 2

[0046] Example 2 Preparation of 5-chlorosalicylaldehyde chitooligosaccharide Schiff base phosphonate

[0047] (1) Preparation of 5-chlorosalicylaldehyde chitooligosaccharide Schiff base

[0048] Soak and swell 6.5852g chitosan oligosaccharide in 50mL absolute ethanol solvent, add 4.6473g 5-chloro salicylaldehyde and 0.9910g NaOH (adjust the pH value of the solution to 7.5-9), microwave heating and reflux reaction for 2h. After the reaction, the product was dried by suction filtration, and the product was extracted with ethanol for 26 hours to remove excess salicylaldehyde and substituted salicylaldehyde in the product, and the product was vacuum-dried at a temperature lower than 50°C. Yield 7.1272g.

[0049] (2) Preparation of 5-chlorosalicylaldehyde chitooligosaccharide Schiff base phosphonate (S-COS-P) 3.2071g

[0050] 2.0484g of the 5-chlorosalicylaldehyde chitooligosaccharide Schiff base (S-COS) prepared in the above step (1) was reacted with 3.2071g of diethyl phosphite...

Embodiment 3

[0051] Example 3 3,5-dichloro salicylaldehyde chitooligosaccharide Schiff base phosphonate

[0052] (1) Preparation of 3,5-dichloro salicylaldehyde chitooligosaccharide Schiff base

[0053] Soak and swell 3.6080g chitosan oligosaccharide in 40mL absolute ethanol solvent, add 3.0732g 3,5-dichlorosalicylaldehyde and 0.2038g NaOH (adjust the pH value of the solution to 7.5-9), microwave heating and reflux reaction for 2.5h. After the reaction, the product was dried by suction filtration, and the product was extracted with ethanol for 27 hours to remove excess salicylaldehyde and substituted salicylaldehyde in the product, and the product was vacuum-dried at a temperature lower than 50°C. Yield 3.756g.

[0054] (2) Preparation of 3,5-dichloro salicylaldehyde chitooligosaccharide Schiff base phosphonate (S-COS-P)

[0055] 1.4653 g of the 3,5-dichloro salicylaldehyde chitooligosaccharide Schiff base (S-COS) prepared in the above step (1) was reacted with 2.7600 g of diethyl phosph...

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Abstract

The invention relates to chitosan oligosaccharide Schiff base phosphonate, which has the structural formula shown in the specification, and in the formula, n is 2-20. The preparation method comprises the following steps of: carrying out chemical modification on chitosan oligosaccharide with salicylaldehyde and substituted salicylaldehyde by adopting a microwave radiation method to obtain a chitosan oligosaccharide Schiff base (S-COS), and then carrying out addition reaction on the S-COS and diethyl phosphite to obtain the chitosan oligosaccharide Schiff base phosphonate. The chitosan oligosaccharide Schiff base phosphonate has better activity for resisting tobacco mosaic virus.

Description

technical field [0001] The invention belongs to the technical field of biological resource pesticide development and utilization, and in particular relates to a chitosan oligosaccharide Schiff base phosphonate and a preparation method and application thereof. Background technique [0002] Tobacco Mosaic Virus (TMV) is one of the main diseases of tobacco. There are 16 kinds of tobacco virus diseases reported so far. above. After the tobacco plants are infected with mosaic disease, the quality of the tobacco leaves will deteriorate and the grade will drop, which will have a great impact on the appearance quality and internal components of the tobacco leaves, reducing the availability of the tobacco leaves, thereby seriously endangering the yield and quality of the tobacco leaves, and often causing huge economic losses. , becoming one of the restrictive factors for the production of high-quality tobacco leaves. From 1989 to 1991, the annual incidence of mosaic disease in majo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/18C07H1/02C08B37/08A01N57/24A01P1/00
Inventor 徐翠莲杨国玉王彩霞樊素芳赵士举
Owner HENAN AGRICULTURAL UNIVERSITY
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