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

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

Examples

Experimental program
Comparison scheme
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Example Embodiment

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

[0035] Take compound A with the structural formula (II) and compound B with the structural formula (III);

[0036]

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

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

[0039]

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

[0041] The chemical equation of the preparation method 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 catalyst is dimethyl sulfoxide, and the organic solvent is ...

Example Embodiment

[0060] Example 1:

[0061] The synthesis 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]pyrimidinamido, 4.8g 2-chloro-4-nitrobenzenesulfonyl chloride, 30mL in a 100mL flask 3,5-lutidine, slowly mechanically stirred, then add 2 drops of DMSO, and react at room temperature for 24 hours.

[0063] After the reaction is complete, filter the product obtained above with filter paper, rinse with a small amount of deionized water, then scrape the filter residue into another 100 mL round bottom flask, and add 30 mL 15% sulfuric acid to the round bottom flask (3.6 g in 36.4 mL water In concentrated sulfuric acid and stir evenly to obtain 15% sulfuric acid) and 10 mL of acetonitrile, continue to mechanically stir for 30 min. At this time, the color changed from dark orange to white. The reaction process was monitored by TLC. The volume ratio of the developing agent is: eth...

Example Embodiment

[0066] Example 2:

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

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

[0069] After the reaction is completed, filter the product obtained above with filter paper, rinse with a small amount of deionized water, then add the filter residue to another 100 mL round bottom flask, add 30 mL 15% sulfuric acid and 10 mL acetonitrile to the round bottom flask, and continue to stir and react for 30 minutes At this time, the color changed from dark orange to white, and the reaction process was monitored by TLC. The developing agent ratio is: ethyl acetate: methanol = 10:1. After the reaction is completed, suction filtration is performed to ob...

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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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