Quinolinone Schiff base compound, and preparation method and application thereof

A compound and drug technology, applied in the field of pesticides, can solve problems such as the use of quinolinone Schiff base compound pesticides and vegetable seed germination accelerators, etc., and achieve excellent insecticidal effect, good poisoning effect, and structure. novel effect

Active Publication Date: 2020-09-29
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there is no report on the use of quinolinone Schiff base compounds as insecticides and vegetable seed germination accelerators

Method used

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  • Quinolinone Schiff base compound, and preparation method and application thereof
  • Quinolinone Schiff base compound, and preparation method and application thereof
  • Quinolinone Schiff base compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0063] The preparation method of said compound specifically comprises the following steps:

[0064] a. Dissolve 2-aminoacetophenone in absolute ethanol, then add NaOH ethanol solution, stir in an ice bath, then add a mixture of compound A and absolute ethanol, and react at 0-5°C;

[0065] b. After the reaction is completed, adjust the pH value of the reaction solution to neutral, then add p-toluenesulfonic acid to the reaction solution, and react at 65-70°C;

[0066] c. After the reaction is completed, pour the reaction solution into ice water, adjust the pH of the solution to 7-9 with triethylamine, and precipitate out, filter, wash until neutral, and then recrystallize with absolute ethanol to obtain the quinolinone intermediate body;

[0067] d. Dissolve the quinolinone intermediate in acetic acid, then add a mixture of cyanoacetylhydrazide and absolute ethanol, and react at 25-35°C. After the reaction is completed, remove the solvent to obtain a solid mixture, and then use ...

Embodiment 1

[0079] Compound 1: preparation of

[0080] 0.01 mol of 2-aminoacetophenone was dissolved in 10 mL of absolute ethanol, and 10 mL of 10% NaOH ethanol solution was added thereto. Stir in an ice bath, slowly drop the mixture of 0.01mol furfural and 10mL absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and check with a thin-layer silica gel plate (TLC) whether the reaction is complete. After the reaction was completed, the pH of the solution was adjusted to neutral with 10% HCl. Then add 0.01mol of p-toluenesulfonic acid to the reaction mixture, react at 65-70°C, and check whether the reaction is complete by TLC. After the reaction is completed, pour the reaction solution into 100 mL of ice water, adjust the pH of the solution to 7-9 with triethylamine, filter, wash with distilled water until neutral, and then recrystallize with absolute ethanol to obtain quinolinone intermediate.

[0081] Dissolve 0.01 mol of homemade ...

Embodiment 2

[0084] Compound 2: preparation of

[0085] 0.01 mol of 2-aminoacetophenone was dissolved in 10 mL of absolute ethanol, and 10 mL of 10% NaOH ethanol solution was added thereto. Stir in an ice bath, slowly drop the mixture of 0.01mol 5-methylfurfural and 10mL absolute ethanol into the above mixed solution with a constant pressure dropping funnel, react at 0-5°C, and use a thin-layer silica gel plate to (TLC) to check the completion of the reaction. After the reaction was completed, the pH of the solution was adjusted to neutral with 10% HCl. Then add 0.01mol of p-toluenesulfonic acid to the reaction mixture, react at 65-70°C, and check whether the reaction is complete by TLC. After the reaction is completed, pour the reaction solution into 100 mL of ice water, adjust the pH of the solution to 7-9 with triethylamine, filter, wash with distilled water until neutral, and then recrystallize with absolute ethanol to obtain quinolinone intermediate.

[0086] Dissolve 0.01 mol o...

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Abstract

The invention relates to the field of pesticides, in particular to a quinolinone Schiff base compound, and a preparation method and application thereof. The technical problem to be solved by the invention is to provide the compound used as an insecticide and a vegetable seed germination accelerator. The structural formula of the compound is shown as a formula I which is described in the specification. In the formula I, X is oxygen, sulfur or nitrogen; and R is hydrogen, a C1-C4 alkyl group, a C1-C4 alkoxy group, a C1-C4 hydroxyalkyl group or halogen. The compound has a good poisoning effect onstored grain insects, and has a good promoting effect on germination of vegetable seeds.

Description

technical field [0001] The invention relates to the field of pesticides, in particular to a quinolinone Schiff base compound and a preparation method and application thereof. Background technique [0002] As we all know, the furan ring is an electron-rich system, and it is easy to form intermolecular hydrogen bonds with various biological enzymes. Therefore, some compounds containing furan rings, whether natural or synthetic, have a broad spectrum of biological activities. Bacteria, anti-virus, anti-tumor, insecticide and weed control etc. At the same time, these compounds usually have the characteristics of high efficiency, low toxicity, safety to non-target organisms, easy degradation in the environment, and resistance to harmful organisms. Therefore, in the research and development of pesticides, compounds containing furan rings showed an increasingly important role. [0003] Thiophene is an important member of heterocyclic compounds and plays a very important role. Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/04C07D409/04A01N43/42A01P21/00A01P7/04
CPCA01N43/42C07D405/04C07D409/04
Inventor 唐孝荣程玮肖婷婷张婷婷陆童钱伟烽蒋文静张桂兰伍微
Owner XIHUA UNIV
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