合成化学2024,Vol.32Issue(9) :833-839.DOI:10.15952/j.cnki.cjsc.1005-1511.23122

三种砜吡草唑主要代谢物的合成

Synthesis of Three Major Metabolites of Pyroxasulfone

李志洋 尹迪 张宇飞 柳红霞 钟玉君 彭雨晴 周昊 谢练武 赵东江
合成化学2024,Vol.32Issue(9) :833-839.DOI:10.15952/j.cnki.cjsc.1005-1511.23122

三种砜吡草唑主要代谢物的合成

Synthesis of Three Major Metabolites of Pyroxasulfone

李志洋 1尹迪 2张宇飞 2柳红霞 2钟玉君 3彭雨晴 3周昊 3谢练武 3赵东江2
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作者信息

  • 1. 中南林业科技大学理学院,湖南长沙 410004;长沙嘉桥生物科技有限公司,湖南长沙 410000
  • 2. 长沙嘉桥生物科技有限公司,湖南长沙 410000
  • 3. 中南林业科技大学理学院,湖南长沙 410004
  • 折叠

摘要

为了满足除草剂代谢物毒理试验的需求,本研究设计并优化了砜吡草唑的3个主要代谢物M1、M3和M4的合成路径.通过全新的合成路径,以1-甲基-3-三氟甲基-4-氯甲基-5-二氟甲氧基-1-H-吡唑为起始原料,经过一系列反应步骤,成功合成了 M1和M3.以2-甲基-2-丙烯酸和溴肟为原料,经过一系列反应后成功合成M4.通过核磁共振氢谱、液相质谱和高效液相色谱等方法对代谢物的结构和纯度进行了确定.经过优化合成工艺,M1、M3和M4的产率分别达到了 76.9%、82.5%和70.1%.合成的代谢物纯度可达97%以上 本研究首次从合成路线的角度出发,成功设计并制备了这3种砜吡草唑代谢物,为农药登记和农残质检等领域提供了重要的研究基础.

Abstract

In order to meet the needs of toxicological tests for the metabolites of the herbicide Pyroxas-ulfone,the present study designed and optimized the synthetic pathways of the three main metabolites of Pyroxasulfone,M1,M3 and M4.Through a novel synthetic pathway,M1,M3 were successfully synthesized from 4-(chloroMethyl)-5-(difluoroMethoxy)-1-Methyl-3-(trifluoroMethyl)-1 H-pyrazole af-ter a series of reaction steps.M4 was successfully synthesized from Methacrylic acid and 1,1-Dibromo-formaldoxime after a number of reactions.The structure and purity of the metabolites were investigated by NMR-hydrogen spectroscopy(NMR-hydrogen spectrometry),liquid mass spectrometry(LMMS),and high-performance liquid chromatography(HPLC).The structure and purity of the metabolites were determined.After optimizing the synthesis process,the yields of M1,M3 and M4 reached 76.9%,82.5%and 70.1%,respectively.The purity of the synthesized metabolites could reach more than 97%.In the present study,these three Pyroxasulfone metabolites were successfully designed and pre-pared from the perspective of synthetic routes for the first time,which provides an important research basis for the fields of pesticide registration and quality control of pesticide residues.

关键词

砜吡草唑/代谢物/合成路径/工艺优化/毒理试验/农药登记

Key words

pyroxasulfone/metabolites/synthesis path/process optimization/toxicology testing/pes-ticide registration

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出版年

2024
合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
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