Triazolopyrimidine sulfonamide compound, and synthetic method and application thereof

A technology of oxazolopyrimidine sulfonamide and synthesis method, which is applied in the field of penoxsulam analogs and synthesis, can solve the problems of high cost and difficulty in synthesizing penoxsulam, and achieves low molecular weight and simple synthesis method. Effect

Active Publication Date: 2013-09-25
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the problems of the existing penoxsulam synthesis difficulty and high cost, and provide triazolopyrimidine sulfonamide compound and its synthesis method and application

Method used

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  • Triazolopyrimidine sulfonamide compound, and synthetic method and application thereof
  • Triazolopyrimidine sulfonamide compound, and synthetic method and application thereof
  • Triazolopyrimidine sulfonamide compound, and synthetic method and application thereof

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specific Embodiment approach 1

[0029] Specific embodiment 1: This embodiment is a triazolopyrimidine sulfonamide compound, the chemical name is 3-chloro-2-methyl-N-(5,8-dimethoxy-[1,2,4]triazole And[1,5-c]pyrimidin-2-yl)benzenesulfonamide, the structural formula is

specific Embodiment approach 2

[0030] Specific embodiment two: This embodiment is the synthesis method of the triazolopyrimidine sulfonamide compound described in specific embodiment one, the chemical name is 3-chloro-2-methyl-N-(5,8-dimethoxy -[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide is specifically completed according to the following steps:

[0031] 1. Preparation of 2-methyl-3-chlorobenzenesulfonyl chloride:

[0032] ①Preparation of diazonium salt: first add glacial acetic acid and concentrated hydrochloric acid to 2-methyl-3-chloroaniline, stir at room temperature to obtain a white precipitate, and then add 2mL / min to 5mL at a temperature of -10°C to -5°C Add dropwise sodium nitrite aqueous solution with a concentration of 0.5g / mL~0.7g / mL at a rate of 1 / min to obtain an orange-yellow solution, keep it at a temperature of -10°C~-5°C for 40min~50min to obtain a diazonium salt; The volume ratio of the described glacial acetic acid to concentrated hydrochloric acid is (0.2~0.4): 1; the volu...

specific Embodiment approach 3

[0042] Specific embodiment three: This embodiment is the application of the triazolopyrimidine sulfonamide compound described in specific embodiment one, the chemical name is 3-chloro-2-methyl-N-(5,8-dimethoxy- [1,2,4]Triazolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide is used as herbicide in paddy fields.

[0043] Mechanism of weeding: The triazolopyrimidine sulfonamide compound described in this embodiment has a chemical name of 3-chloro-2-methyl-N-(5,8-dimethoxy-[1,2,4]tri Azolo[1,5-c]pyrimidin-2-yl)benzenesulfonamide is an inhibitor of acetolactate synthase, which achieves herbicidal effect by inhibiting the synthesis of proteins in plants. Its mechanism of action is similar to that of sulfonylurea herbicides. similar. After plants absorb triazolopyrimidine sulfonamide herbicides, the activity of ALS in the body is severely reduced, and the synthesis of valine, leucine and isoleucine is greatly threatened, which hinders the synthesis of proteins and causes plant growth to st...

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Abstract

The invention provides a triazolopyrimidine sulfonamide compound and synthetic methods and application thereof, relating to a penoxsulam analog and a synthetic method and application thereof. The objective of the invention is to overcome the problems of great synthesis difficulty and high cost of conventional penoxsulam. The triazolopyrimidine sulfonamide compound has a structural formula described in the specification. The method 1 comprises the following steps: 1, preparing 2-methyl-3-chlorobenzenesulfonyl chloride; and 2 preparing a finished product so as to obtain 3-chloro-2-methyl-N-(5,8-dimethoxy-[1,2,4] triazolo[1,5-c]pyrimidine-2-yl) benzsulfamide. The method 2 comprises the following steps: 1, preparing 2-mercapto-3-trifluoromethylpyridine; and 2, preparing 3-trifluoromethylpyridine-2-sulfonyl chloride; and 3, preparing a finished product so as to obtain 3-trifluoro-methyl-N-(5,8-dimethoxy-[1,2,4] triazolo[1,5-c]pyrimidine-2-yl) pyridine sulfamide. The triazolopyrimidine sulfonamide compound is used as a herbicide in a rice field.

Description

technical field [0001] The invention relates to a penoxsulam analogue, a synthesis method and an application. Background technique [0002] Penoxsulam is a new herbicide for paddy fields developed by Dow Company in the United States in the 21st century. It was promoted in Europe in 2005 and officially registered in my country in 2008. Sedge and a variety of broad-leaved grasses have good control effects. This herbicide has high activity, strong selectivity, wide herbicidal spectrum, low dosage, fast degradation speed, and most importantly, it is safe for subsequent crops. It is the latest paddy field herbicide on the market and is widely known as "Dao Jie". [0003] The structural formula of penoxsulam is as follows: [0004] However, the existing penoxsulam is difficult to synthesize, high in cost and expensive, and is greatly restricted in use and popularization. Contents of the invention [0005] The purpose of the present invention is to solve the problems of the ex...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P13/00
CPCA01N43/90C07D487/04
Inventor 闫鹏飞周金枝高金胜马东升苏少泉
Owner HEILONGJIANG UNIV
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