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3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy) and their application

A 2-a, derivative technology, used in applications, biocides, chemicals for biological control, etc., can solve problems such as unreported research on agricultural antibacterial activity

Active Publication Date: 2021-11-16
GUIZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the research on the antibacterial activity of six-membered ring mesoionic compounds in agriculture

Method used

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  • 3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy) and their application
  • 3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy) and their application
  • 3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy) and their application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1: 1-(4-Hydroxy-methoxybenzyl)-3-methyl-2-oxo-1,2-dihydropyrido[1,2-a]pyrimidin-5-ium-4 -Synthetic (compound numbering is A1) of phenate, comprises the following steps:

[0059] (1) Use 2-methylmalonic acid (10mmol), 2,4,6-trichlorophenol (20mmol), and 30 mL of phosphorus oxychloride as solvents, and heat to reflux for 4 to 6 hours. After the reaction is completed, the reaction system Slowly drop into 200mL ice water with magnetic stirring and stir well. After the temperature dropped to room temperature, the white solid was collected by filtration to obtain the intermediate bis(2,4,6-trichlorophenyl)-2-methylmalonate;

[0060] (2) Add 2-aminopyridine (2.0mmol), vanillin (1.5mmol) and DCE 30mL as a solvent into a 100mL three-neck flask for reflux reaction for 3-5h. Add NaBH to the system in batches after the reaction conversion is complete 4 (4.0mmol) as a reducing agent, reflux reaction for 1-2h, after the reaction is completed, remove the solvent under reduc...

Embodiment 2

[0062] Example 2: 1-(4-((2,4-dichlorobenzyl)oxy)-3-methoxybenzyl)-3-methyl-2-oxo-1,2-dihydropyridine The synthesis of [1,2-a] pyrimidine-5-ium-4-phenol salt (the compound number is A2) comprises the following steps:

[0063] (1) with the (1) step of embodiment 1;

[0064] (2) Add vanillin (5.0mmol), potassium carbonate (15.0mmol), 2,3-dichlorobenzyl chloride (6.0mmol), and 30mL of acetonitrile as solvent into a 100mL three-necked flask, and reflux for 3-5h. After the reaction was completed, ice water was added for washing, and then the solid intermediate 4-((2,4-dichlorobenzyl)oxy)-3-methoxybenzaldehyde was collected by filtration;

[0065] (3) 2-aminopyridine (2.0mmol), 4-((2,4-dichlorobenzyl)oxy)-3-methoxybenzaldehyde (1.5mmol), with DCE 30mL as solvent, was added to Reflux reaction in a 100mL three-neck flask for 3-5 hours. After the reaction is converted, add NaBH to the system in batches 4 (4.0mmol) as a reducing agent, reflux reaction for 1-2h, after the reaction is ...

Embodiment 3

[0067]Example 3: 1-(4-((3-chlorobenzyl)oxy)-3-methoxybenzyl)-3-methyl-2-oxo-1,2-dihydropyrido[1 , 2-a] the synthetic (compound number is A3) of pyrimidin-5-ium-4-phenol salt, comprises the following steps:

[0068] (1) with the (1) step of embodiment 1;

[0069] (2) Add vanillin (5.0mmol), potassium carbonate (15.0mmol), 3-chlorobenzyl chloride (6.0mmol), and 30mL of acetonitrile as a solvent into a 100mL three-necked flask, and reflux for 3-5h. After the reaction is completed, Add ice water to wash, then collect the solid intermediate 4-((3-chlorobenzyl)oxy)-3-methoxybenzaldehyde by filtration;

[0070] (3) Add 2-aminopyridine (2.0mmol), 4-((3-chlorobenzyl)oxy)-3-methoxybenzaldehyde (2.0mmol) to a 100mL three-necked flask with DCE 30mL as solvent Medium reflux reaction for 3 to 5 hours. After the reaction is converted, add NaBH to the system in batches 4 (4.0mmol) as a reducing agent, reflux reaction for 1-2 h, after the reaction was completed, the solvent was removed und...

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Abstract

The invention discloses a 3-methylpyrido[1,2-a]pyrimidinone derivative containing 1-((4-substituted benzyl)oxy) and its application. Its general formula is as follows, wherein: R 1 is methoxy, ethoxy, chlorine, bromine; R 2 is hydrogen, sec-butyl, ethyl, propyl, chloroethyl, benzyl, 2,4-dichlorobenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-trifluoromethylbenzyl, 2-chloropyridine-5-methylene, 2-chlorothiazole-5-methylene, 4-bromobenzyl, 2-methoxybenzyl, 3-methoxybenzyl; 2-fluorobenzyl, 2 ‑Cyanobenzyl, 4‑Cyanobenzyl, 2‑Methylbenzyl, 3‑Methylbenzyl or 4‑Methylbenzyl. The compound of the invention can prevent and treat rice bacterial blight and citrus canker.

Description

technical field [0001] The present invention relates to the field of chemical technology, in particular to a class of 3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy), and also to The preparation method of the 3-methylpyrido[1,2-a]pyrimidinone derivatives containing 1-((4-substituted benzyl)oxy), and the 1-((4-substituted benzyl ) Oxygen) 3-methylpyrido[1,2-a]pyrimidinone derivatives in the application of resistance to rice bacterial blight and citrus canker disease. Background technique [0002] Rice is one of the main food crops in my country, but the current bacterial diseases have caused huge losses to rice. Among them, rice bacterial blight is the main bacterial disease in rice production, which seriously threatens the safe production of rice. At present, there is a lack of high-efficiency and green pesticides that can prevent and control rice bacterial blight in pesticide production. Mesoions are a class of compounds that have e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N43/90A01P3/00
CPCA01N43/90C07D471/04
Inventor 胡德禹刘登曰宋宝安赵磊何文静刘峥军韦春乐张雨
Owner GUIZHOU UNIV