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Triazole pyrimidine sulphonates compound, preparing method and application thereof

A technology of azolopyrimidine sulfonate and compound, applied in the field of triazolopyrimidine sulfonate compound and its preparation and application

Inactive Publication Date: 2007-08-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When the inventors conducted research in this field, they synthesized a new class of triazolopyrimidine sulfonate compounds, and found that they have good herbicidal and plant growth regulating activities. There is no report on this type of compound yet.

Method used

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  • Triazole pyrimidine sulphonates compound, preparing method and application thereof
  • Triazole pyrimidine sulphonates compound, preparing method and application thereof
  • Triazole pyrimidine sulphonates compound, preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 Synthesis of O-(1,2,4-triazolo[1,5-a]pyrimidin-2-yl)-4-methylbenzenesulfonate (compound 1)

[0035] In a 50mL three-necked flask, add 0.66g (0.004mol) 2-hydroxyl-5,7-dimethyl-1,2,4-triazol[1,5-a]pyrimidine, 0.16g (0.004mol) hydroxide Sodium, 20mL water, dissolved by magnetic stirring, drop into 5mL ether solution of 0.77g (0.004mol) p-toluenesulfonyl chloride at room temperature, about 0.5h after dripping, there is solid formation, continue to stir for 5h, distill off the ether under reduced pressure, pump The gray solid was obtained by filtration, washed with 3% hydrochloric acid aqueous solution and 5% sodium bicarbonate aqueous solution respectively, and then washed several times with water, dried, and subjected to silica gel column chromatography, petroleum ether-acetone (50 / 50, v / v) as solvent , to obtain colorless flaky crystal compound 1 with a yield of 85.0% and a melting point of 149°C to 151°C.

[0036] 1 H NMR (internal standard TMS, solvent is CD...

Embodiment 20

[0040] Synthesis of Example 20-(1,2,4-triazolo[1,5-a]pyrimidin-2-yl)-benzenesulfonate (compound 2)

[0041] In a 50mL three-necked flask, add 0.66g (0.004mol) 2-hydroxyl-5,7-dimethyl-1,2,4-triazol[1,5-a]pyrimidine, 0.16g (0.004mol) hydroxide Sodium, 20mL water, magnetically stirred to dissolve, drop 0.71g (0.004mol) benzenesulfonyl chloride in 5mL ether solution at room temperature, after about 0.5h, a solid was formed, continue to stir for 5h, distill off the ether under reduced pressure, filter with suction A gray solid was obtained, which was washed with 3% hydrochloric acid aqueous solution and 5% sodium bicarbonate aqueous solution, and then washed several times with water, dried, and subjected to silica gel column chromatography, petroleum ether-acetone (70 / 30, v / v) as solvent, Compound 2 was obtained as colorless columnar crystals with a yield of 88.0% and a melting point of 145°C to 147°C.

[0042] 1 H NMR (internal standard TMS, solvent is CDCl 3 ): δppm

[0043] ...

Embodiment 30

[0046] Synthesis of Example 30-(1,2,4-triazolo[1,5-a]pyrimidin-2-yl)-4-nitrobenzenesulfonate (compound 3)

[0047] In a 50mL three-necked flask, add 0.66g (0.004mol) 2-hydroxy-5,7-dimethyl-1,2,4-triazol[1,5-a]pyrimidine, 0.21g (0.004mol) sodium carbonate , 20mL of water, magnetically stirred to dissolve, drop 0.89g (0.004mol) 4-nitrobenzenesulfonyl chloride in 10mL of methyl tert-butyl ether solution at room temperature, after about 0.5h, a solid was formed, continue to stir for 5h, Methyl tert-butyl ether was evaporated under reduced pressure, a gray solid was obtained by suction filtration, washed with 3% hydrochloric acid aqueous solution and 5% sodium bicarbonate aqueous solution, and then washed several times with water, dried, and subjected to silica gel column chromatography, petroleum ether- Acetone (70 / 30, v / v) was used as solvent to obtain white columnar crystal compound 3 with a yield of 92.0%.

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Abstract

The invention discloses a making method of triazolopyrimidosulfonate compound and application, whose chemical formula is as formula (I), wherein R1, R2 and R3 is individual H, C1-C4 alkyl or C1-C4 alkoxy; X1, X2, X3, X4 and X5 is individual H, halogen, nitro radical, C1-C4 alkyl or C1-C4 alkoxy; the compound possesses excellent weeding and plant growing and adjusting activity.

Description

(1) Technical field [0001] The invention relates to a triazolopyrimidine sulfonate compound, a preparation method and application thereof. (2) Background technology [0002] Heterocyclic compounds have become the mainstream in the development of new pesticides, and in heterocyclic compounds, nitrogen-containing heterocycles are the main ones. Triazolopyrimidine heterocyclic compounds have a broad spectrum of biological activities due to the fact that their molecular structure contains two important active structural units, triazole and pyrimidine, and a new type of acetolactate synthase (ALS) has been successfully developed. ) Inhibitor super-efficient herbicides DE498 (Kaocaoqing), DE511 (sulfentrazone) and other pesticide varieties; in recent years, research on the structure optimization and biological activity of triazolopyrimidine compounds is still very active. During the research in this field, the inventor synthesized a new class of triazolopyrimidine sulfonate compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P21/00A01P13/00
Inventor 孙国香沈德隆周红芳屠美玲
Owner ZHEJIANG UNIV OF TECH