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Triazolopyrimidine sulfonamide compound, and synthetic method and application thereof

The technology of an azolopyrimidine sulfonamide and its synthesis method is applied in the field of penoxsulam analogs and synthesis, which can solve the problems of high difficulty and high cost of penoxsulam synthesis, and achieve the effect of small molecular weight and simple synthesis method

Active Publication Date: 2015-04-08
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~5mL at a temperature of -10°C~-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 described glacial acetic acid and concentrated hydrochloric acid is (0.2~0.4): 1; The quality of de...

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

A triazolopyrimidine sulfonamide compound and a synthesis method and use thereof; the present invention relates to a penoxsulam analogue and a synthesis method and use thereof. An object of the present invention is to solve the existing problems that the synthesis of penoxsulam is greatly difficult and has high costs. A triazolopyrimidine sulfonamide compound of structural formula (I) or (II); method 1: (1) preparing a 2-methyl-3-chlorobenzenesulfonyl chloride; (2) preparing a finished product, that is to say obtaining 3-chloro-2-methyl-N-(5,8-dimethoxyl-[1,2,4]triazolo[1,5-c]pyrimidine-2-yl)benzene sulfonamide. Method 2: (1) preparing 2-mercapto-3-trifluoromethyl pyridine; (2) preparing 3-trifluoromethyl pyridine-2-sulfonyl chloride; (3) preparing a finished product, that is to say obtaining 3-trifluoromethyl-N-(5,8-dimethoxyl-[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)pyridine sulfonamide. The triazolopyrimidine sulfonamide compound is used as a rice field herbicide.

Description

Technical field [0001] The invention involves split -sulfonal analogs and synthesis methods and applications. Background technique [0002] Fluorosaulsecopy is a new type of rice fields developed by Dow's 21st century. It was promoted in Europe in 2005 and officially registered in my country in 2008. Disposal and a variety of broad -leaved grass have good prevention. This herbicide has high activity, strong selectivity, wide -ranging spectrum, low amount, and fast degradation. It is currently the latest paddy field herbicide in the market, which is widely known as "Dajie". [0003] Fluorosaomanide structured formats are as follows: Essence [0004] However, the synthesis of the existing splum sulfurizer is difficult, the cost is high, and the price is expensive. It has been greatly restricted in use and promotion. Invention content [0005] The purpose of the present invention is to solve the problem of existing pinofluorosulfidaic acid synthesis and high costs, and provides tr...

Claims

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Application Information

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Patent Type & Authority Patents(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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