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放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析

杨征敏 宋明钰 陈沪飞 余志扬 周迪 夏燕婷 郑东敏 薛晓娅

杨征敏, 宋明钰, 陈沪飞, 余志扬, 周迪, 夏燕婷, 郑东敏, 薛晓娅. 放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析[J]. 农药学学报, 2020, 22(1): 19-26. doi: 10.16801/j.issn.1008-7303.2020.0003
引用本文: 杨征敏, 宋明钰, 陈沪飞, 余志扬, 周迪, 夏燕婷, 郑东敏, 薛晓娅. 放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析[J]. 农药学学报, 2020, 22(1): 19-26. doi: 10.16801/j.issn.1008-7303.2020.0003
YANG Zhengmin, SONG Mingyu, CHEN Hufei, YU Zhiyang, ZHOU Di, XIA Yanting, ZHENG Dongmin, XUE Xiaoya. Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole[J]. Chinese Journal of Pesticide Science, 2020, 22(1): 19-26. doi: 10.16801/j.issn.1008-7303.2020.0003
Citation: YANG Zhengmin, SONG Mingyu, CHEN Hufei, YU Zhiyang, ZHOU Di, XIA Yanting, ZHENG Dongmin, XUE Xiaoya. Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole[J]. Chinese Journal of Pesticide Science, 2020, 22(1): 19-26. doi: 10.16801/j.issn.1008-7303.2020.0003

放射性同位素碳-14标记氯虫苯甲酰胺的合成与分析

doi: 10.16801/j.issn.1008-7303.2020.0003
详细信息
    通讯作者:

    杨征敏,通信作者 (Author for correspondence),男,博士,技术总监,主要从事功能化学品的放射性同位素标记合成与代谢研究,E-mail:zmyang@qzisotech.com

  • 中图分类号: O628.21;S482.3

Synthesis and analysis of radioisotope carbon-14 labelled chlorantraniliprole

  • 摘要: 以 [ 14C ] 碳酸钡为放射性同位素原料,通过格氏反应、亲核取代、胺化和缩合等8步放化反应制备了2种放射性同位素碳-14 标记的氯虫苯甲酰胺粗品,经反相高效液相色谱(RP-HPLC)纯化获得标记物纯品14C-氯虫苯甲酰胺 [ 3-溴-N- [ 4-氯-2-甲基-6-( 甲氨基 [ 羰基-14C ] 甲酰基) 苯基 ] -1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺 ( 2 , 55.6 mCi)和3-溴-N- [ 4-氯-2-甲基-6- (甲氨基甲酰基) 苯基 ] -1-(3-氯-2-吡啶基)-1H-吡唑-5- [ 羰基-14C ] 甲酰胺 ( 3 , 58.6 mCi) ] 。以 [ 14C ] 碳酸钡计,两种标记物的总放化收率分别为32%和52%。其结构经核磁共振氢谱、质谱和在线放射性高效液相色谱 (HPLC-FSA) 分析确认。放射性薄层成像分析 (TLC-IIA)、离线放射性高效液相色谱分析(HPLC-LSC)、在线放射性高效液相色谱-二极管阵列检测器/质谱联用 (HPLC-FSA/PDA/MS) 和LSC分析表明,两种14C-氯虫苯甲酰胺的放化纯度分别为99.8%和99.6%,化学纯度分别为99.1%和98.4%,比活度分别为52.45 mCi/mmol和52.30 mCi/mmol。这2种标记物可作为放射性示踪剂,可满足氯虫苯甲酰胺在中国的登记代谢试验研究的需要。
  • 1  氯虫苯甲酰胺 (1) 及其放射性同位素碳-14标记物 ( *表示碳-14标记位点)

    1.  Chlorantraniliprole (1) and its radioisotope carbon-14 labelled counterparts(*indicates carbon-14 labelled sites)

    2  [ 苯甲酰胺羰基-14C] 氯虫苯甲酰胺 (2) 的合成路线 (*表示碳-14标记位点)

    2.  Synthetic route of [benzamide carbonyl-14C]chlorantraniliprole 2 (*indicates carbon-14 labelled sites)

    3  [ 吡唑甲酰胺羰基-14C] 氯虫苯甲酰胺 (3) 的合成路线 (*表示碳-14标记位置)

    3.  Synthetic route of [pyrazolylamide carbonyl-14C]chlorantraniliprole 3 (*indicates carbon-14 labelled sites)

    图  1  碳-14标记氯虫苯甲酰胺 (2) 的离线放射性高效液相色谱图 (HPLC-LSC)

    Figure  1.  Offline radio-chromatogram (HPLC-LSC) of the carbon-14 labelled chlorantraniliprole (2)

    图  2  碳-14标记氯虫苯甲酰胺 (2) 的高效液相色谱图(HPLC-UV)

    Figure  2.  High performance liquid chromatogram of the carbon-14 labelled chlorantraniliprole (2)

    4  丙酯草醚 (15)、氯虫苯甲酰胺 (16) 和环磺酮 (17) 分子中的标记单元

    4.  Radiolabelling units of pyribambenz-propyl (15), chlorantraniliprole (16) and tembotrione (17)

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  • 收稿日期:  2019-05-14
  • 录用日期:  2019-07-02
  • 刊出日期:  2020-02-01

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