Triazolopyrimidine sulfonamide compound as well as preparation method and application thereof

A technology for azolopyrimidine sulfonamides and compounds, which is applied in the field of triazolopyrimidine sulfonamide compounds and their preparation, can solve the problems of penoxsulam complex structure, difficult synthesis, and high cost, and achieve simple and easy preparation methods Operation, strong selectivity, low cost effect

Active Publication Date: 2018-08-14
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the existing penoxsulam has a complex structure, great difficulty in synthesis, and high cost

Method used

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  • Triazolopyrimidine sulfonamide compound as well as preparation method and application thereof
  • Triazolopyrimidine sulfonamide compound as well as preparation method and application thereof
  • Triazolopyrimidine sulfonamide compound as well as preparation method and application thereof

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preparation example Construction

[0034] One embodiment of the present invention provides a method for preparing triazolopyrimidine sulfonamide compounds, comprising the following steps:

[0035] Take the compound A whose structural formula is shown in formula (II) and the compound B whose structural formula is shown in formula (III);

[0036]

[0037] Wherein, R is a chlorine atom or a methoxycarbonyl group;

[0038] The compound A and the compound B are added into an organic solvent according to a molar ratio of 1:(1.1-1.4), and reacted at room temperature for 18-24h in the presence of a catalyst to obtain a structural formula as shown in formula (I) Triazolopyrimidine sulfonamide compounds,

[0039]

[0040] Wherein, R is a chlorine atom or a methoxycarbonyl group.

[0041] The preparation method chemical equation of compound I involved in the present invention is as follows:

[0042]

[0043] Optionally, the molar ratio of the compound A to the compound B is 1:1.2.

[0044] Optionally, the cat...

Embodiment 1

[0061] The synthetic process of N-(4,7-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine)-2-chloro-4-nitrobenzenesulfonamide (I-a) is as follows:

[0062] Add 3.0g 4,7-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidineamino, 4.8g 2-chloro-4-nitrobenzenesulfonyl chloride, 30mL in a 100mL flask 3,5-lutidine, stirred slowly mechanically, then added 2 drops of DMSO, and reacted at room temperature for 24h.

[0063] After the reaction was completed, the above-mentioned resulting product was filtered with filter paper, rinsed with a small amount of deionized water, then the filter residue was scraped into another 100mL round-bottomed flask, and 30mL of 15% sulfuric acid was added to the round-bottomed flask (3.6g was added in 36.4mL of water) 15% sulfuric acid) and 10 mL of acetonitrile, and continued mechanical stirring for 30 min. At this time, the color changed from dark orange to white, and the reaction process was monitored by TLC. The volume ratio of the developer is: ethyl acetate:methanol=1...

Embodiment 2

[0067] N-(4,7-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine)-2-methoxycarbonyl-4-nitrobenzenesulfonamide (I-b) synthesis process is as follows :

[0068] Add 2g 4,7-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidineamino, 3.35g 2-methoxycarbonyl-4-nitrobenzene in a 100ml single-necked round bottom flask Sulfonyl chloride, 20ml 3,5-lutidine, add 2 drops of DMSO, react at room temperature for 18h.

[0069] After the reaction is complete, filter the above-mentioned product with filter paper, rinse with a small amount of deionized water, then add the filter residue to another 100mL round-bottom flask, add 30mL of 15% sulfuric acid and 10mL of acetonitrile to the round-bottom flask, and continue stirring for 30min , the color changed from dark orange to white at this time, and the reaction process was monitored by TLC. The developer ratio is: ethyl acetate: methanol = 10:1. After the reaction was completed, it was filtered with suction to obtain a white solid, which was separated by silica g...

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Abstract

The invention provides a triazolopyrimidine sulfonamide compound, which has a structural formula as shown in the formula (I) as below, wherein R is a chlorine atom or a methoxycarbonyl group. According to triazolopyrimidine sulfonamide compound provided by the invention, an ortho-position and a para-position on a benzene ring are substituted, a para-substituent is nitryl, and an ortho-substituentis the chlorine atom or the methoxycarbonyl group. The compound is simple in structure, and has higher weeding activity and higher safety on crops at the same time. The invention also provide a preparation method and application of the triazolopyrimidine sulfonamide compound.

Description

technical field [0001] The invention relates to a triazolopyrimidine sulfonamide compound and a preparation method and application thereof. Background technique [0002] Triazolopyrimidine sulfonamide herbicides are a class of herbicides that develop rapidly. Among them, penoxsulam is the most typical class of triazolopyrimidine sulfonamide compounds. Penoxsulam is a post-emergence herbicide for rice fields developed by Tao Nongke Company of the United States. It works by inhibiting acetolactate synthase (ALS). It was officially registered with the US EPA on September 24, 2004. It was promoted and applied in the southern rice fields of the United States in 2005, and it was registered in China in 2008. The structure of penoxsulam is as follows: [0003] [0004] However, the existing penoxsulam has complex structure, great difficulty in synthesis and high cost. Therefore, it is necessary to provide a new triazolopyrimidine sulfonamide compound. Contents of the invent...

Claims

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Application Information

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IPC IPC(8): C07D487/04A01N43/90A01P13/00
CPCA01N43/90C07D487/04
Inventor 王明良李定雄尹春慧何雅慧马晨生朱才镇
Owner SHENZHEN UNIV
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