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Lignin derivatives as well as preparation method and use thereof

A technology of lignans and derivatives, applied in botany equipment and methods, chemicals for biological control, biocides, etc.

Inactive Publication Date: 2013-12-25
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in recent years, the widespread and unscientific use of various fungicides has caused various pathogenic bacteria in my country's farmland to produce obvious resistance to existing traditional fungicides (Jia Junchao, Ma Lin, Fan Zhijin, etc. Journal of Pesticide Science, 2008 , 10(1):1-9), for example, methoxyacrylate fungicides were once one of the most widely used fungicides in my country's farmland, and they have also produced obvious resistance in China's farmland at present (Zhao Ping, Yan Qiuxu , Li Xin et al. Pesticides, 2011, 50(8): 547-542)

Method used

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  • Lignin derivatives as well as preparation method and use thereof
  • Lignin derivatives as well as preparation method and use thereof
  • Lignin derivatives as well as preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of intermediate 5-methyl-1,2,3-thiadiazole-4-carbonyl chloride:

[0033] Add 67 mmoles of 5-methyl-1,2,3-thiadiazole-4-carboxylic acid and 29 milliliters of thionyl chloride into a 100 milliliter three-necked round-bottomed flask, heat and reflux at 80 degrees Celsius for 6 hours, and depressurize Distill off excess thionyl chloride, and collect fractions at 94-96 degrees Celsius under reduced pressure at 2000 Pa to obtain 9.25 grams of light yellow product, yield 85%, intermediate 5-methyl-1,2,3-thiadiazole -4-Formyl chloride is sealed and stored in a desiccator for later use.

Embodiment 2

[0035] The preparation of lignan ether compound I:

[0036] Add 0.53 mmol of raw material II to a 50 ml round bottom flask, then add 20 ml of anhydrous acetone and 1.06 mmol of anhydrous potassium carbonate, stir at room temperature for 30 minutes, then add 0.53 mmol of halogenated hydrocarbon R 1 -X, heated to reflux for 12 hours, cooled the reaction system, filtered to remove the solid, and removed the solvent by rotary evaporation. The crude product was purified by 200-300 mesh silica gel column chromatography to obtain light yellow solid lignan ether compound I. The eluent was Petroleum ether at 61 to 93 degrees Celsius: ethyl acetate, the volume ratio is 3:1; the yield is calculated with the obtained pure product, and the yield is 58-64%. Its physical and chemical parameters and structural parameters are listed in Table 1. The halogenated hydrocarbon R 1 -X is selected from: 3-bromopropyne, 5-chloro-4-chloromethyl 1,2,3-thiadiazole, 1,1,3-trichloropropene, bromomethylcy...

Embodiment 3

[0038] Add 0.53 mmol of raw material II to a 50 ml round-bottomed flask, then add 20 ml of chloroform and 0.8 mmol of triethylamine, stir at room temperature for 10 minutes, and slowly add acid chloride R dropwise under ice-bath conditions. 1 -X in chloroform solution, stirred in ice bath for 0.5 hours, then reacted at room temperature for 3 hours, added ammonium chloride to stop the reaction, added 50 mL of chloroform to dilute, washed with saturated sodium bicarbonate (3×10 mL), anhydrous Dry over sodium sulfate and concentrate under reduced pressure. The crude product is purified by 200-300 mesh silica gel column chromatography to obtain light yellow solid lignan ester compound I. The eluent is petroleum ether at 61-93 degrees Celsius: ethyl acetate, according to the product The difference is that the volume ratio is 3:1; the yield is calculated with the obtained pure product, and the yield is 55.9%. Its physical and chemical parameters and structural parameters are listed ...

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PUM

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Abstract

The invention provides lignin derivatives as well as a preparation method and use thereof. The invention relates to compounds containing lignin, and the compounds have a chemical structure general formula represented by a formula I. The invention discloses a structural general formula and a synthetic method of the compounds, application of the compounds used as an antiviral agent and a bactericide, and a processing technology for preparing the antiviral agent and the bactericide by mixing the compounds with agriculturally acceptable auxiliaries or synergists. The invention further discloses application of the compounds in preventing and treating diseases, insect attack, mite attack and virus diseases in agriculture, forestry and horticulture in combination with an insecticide, a miticide, a bactericide, acetylglucosyl bromide and a plant activator and preparation methods of the compounds. The invention further discloses antineoplastic activity of the compounds and application thereof in treating tumors.

Description

technical field [0001] The technical solution of the invention relates to lignan-containing derivatives, in particular to lignan ether and ester compounds. Background technique [0002] Viruses, fungi, bacteria, etc. are one of the important factors affecting modern agricultural production. Various diseases caused by these pathogens seriously affect the yield and quality of agricultural products. Various chemical fungicides are one of the important means to ensure the reduction of diseases and the yield and quality of agricultural products. However, in recent years, the widespread and unscientific use of various fungicides has caused various pathogenic bacteria in my country's farmland to produce obvious resistance to existing traditional fungicides (Jia Junchao, Ma Lin, Fan Zhijin, etc. Journal of Pesticide Science, 2008 , 10(1):1-9), for example, methoxyacrylate fungicides were once one of the most widely used fungicides in my country's farmland, and they have also produce...

Claims

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Application Information

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IPC IPC(8): C07D417/14C07D407/04C07D317/60A01N43/828A01N43/30A01P1/00A01P3/00A01P7/02A01P7/04A01P21/00A61K31/433A61K31/365A61K31/36A61P35/00
Inventor 范志金姬晓恬余建华李娟娟华学文宗广宁李凤云刘超伦朱玉洁陈来
Owner NANKAI UNIV
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