(E) N'-carbamoyl-N[(6-chloropyridin-3-yl)methyl]-N-methylacetimidamide | 215366-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E) N'-carbamoyl-N[(6-chloropyridin-3-yl)methyl]-N-methylacetimidamide
• 英文别名: (E)-N'-Carbamoyl-N-((6-chloropyridin-3-yl)methyl)-N-methylacetimidamide；(E)-1-[(6-chloropyridin-3-yl)methyl-methylamino]ethylideneurea
• CAS: 215366-29-3
• 化学式: C₁₀H₁₃ClN₄O
• 分子量: 240.692
• InChiKey: ISBUGOZWWNMPPC-VGOFMYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E) N'-carbamoyl-N[(6-chloropyridin-3-yl)methyl]-N-methylacetimidamide 以 aq. phosphate buffer 为溶剂， 反应 96.0h， 生成 1-(6-氯-3-嘧啶基)-N-甲基甲胺 1.4 HCl
  参考文献：
  名称：

  Degradation of the Neonicotinoid Insecticide Acetamiprid via the N-Carbamoylimine Derivate (IM-1-2) Mediated by the Nitrile Hydratase of the Nitrogen-Fixing Bacterium Ensifer meliloti CGMCC 7333

  摘要：

  The metabolism of the widely used neonicotinoid insecticide acetamiprid (ACE) has been extensively studied in plants, animals, soils, and microbes. However, hydration of the N-cyanoimine group in ACE to the N-carbamoylimine derivate (IM-1-2) by purified microbes, the enzyme responsible for this biotransformation, and further degradation of IM-1-2 have not been studied. The present study used liquid chromatographymass spectrometry and nuclear magnetic resonance spectroscopy to determine that the nitrogen-fixing bacterium Ensifer meliloti CGMCC 7333 transforms ACE to IM-1-2. CGMCC 7333 cells degraded 65.1% of ACE in 96 h, with a half-life of 2.6 days. Escherichia coli Rosetta (DE3) overexpressing the nitrile hydratase (NHase) from CGMCC 7333 and purified NHase converted ACE to IM-1-2 with degradation ratios of 97.1% in 100 min and 93.9% in 120 min, respectively. Interestingly, IM-1-2 was not further degraded by CGMCC 7333, whereas it was spontaneously hydrolyzed at the N-carbamoylimine group to the derivate ACE-NH2, which was further converted to the derivative ACE-NH2. Then, ACE-NH2 was cleaved to the major metabolite IM-1-4. IM-1-2 showed significantly lower insecticidal activity than ACE against the aphid Aphis craccivora Koch. The present findings will improve the understanding of the environmental fate of ACE and the corresponding enzymatic mechanisms of degradation.

  DOI：

  10.1021/jf503557t
• 作为产物：
  描述：

  啶虫脒 在 Escherichia coli Rostta (DE₃) cells overexpressing nitrile hydratase from Ensifer meliloti CGMCC 7333 作用下， 以 aq. phosphate buffer 为溶剂， 反应 96.0h， 生成 (E) N'-carbamoyl-N[(6-chloropyridin-3-yl)methyl]-N-methylacetimidamide
  参考文献：
  名称：

  Degradation of the Neonicotinoid Insecticide Acetamiprid via the N-Carbamoylimine Derivate (IM-1-2) Mediated by the Nitrile Hydratase of the Nitrogen-Fixing Bacterium Ensifer meliloti CGMCC 7333

  摘要：

  The metabolism of the widely used neonicotinoid insecticide acetamiprid (ACE) has been extensively studied in plants, animals, soils, and microbes. However, hydration of the N-cyanoimine group in ACE to the N-carbamoylimine derivate (IM-1-2) by purified microbes, the enzyme responsible for this biotransformation, and further degradation of IM-1-2 have not been studied. The present study used liquid chromatographymass spectrometry and nuclear magnetic resonance spectroscopy to determine that the nitrogen-fixing bacterium Ensifer meliloti CGMCC 7333 transforms ACE to IM-1-2. CGMCC 7333 cells degraded 65.1% of ACE in 96 h, with a half-life of 2.6 days. Escherichia coli Rosetta (DE3) overexpressing the nitrile hydratase (NHase) from CGMCC 7333 and purified NHase converted ACE to IM-1-2 with degradation ratios of 97.1% in 100 min and 93.9% in 120 min, respectively. Interestingly, IM-1-2 was not further degraded by CGMCC 7333, whereas it was spontaneously hydrolyzed at the N-carbamoylimine group to the derivate ACE-NH2, which was further converted to the derivative ACE-NH2. Then, ACE-NH2 was cleaved to the major metabolite IM-1-4. IM-1-2 showed significantly lower insecticidal activity than ACE against the aphid Aphis craccivora Koch. The present findings will improve the understanding of the environmental fate of ACE and the corresponding enzymatic mechanisms of degradation.

  DOI：

  10.1021/jf503557t

文献信息

• Degradation of the Neonicotinoid Insecticide Acetamiprid via the <i>N</i>-Carbamoylimine Derivate (IM-1-2) Mediated by the Nitrile Hydratase of the Nitrogen-Fixing Bacterium <i>Ensifer meliloti</i> CGMCC 7333
  作者：Ling-Yan Zhou、Long-Jiang Zhang、Shi-Lei Sun、Feng Ge、Shi-Yun Mao、Yuan Ma、Zhong-Hua Liu、Yi-Jun Dai、Sheng Yuan

  DOI：10.1021/jf503557t

  日期：2014.10.15

  The metabolism of the widely used neonicotinoid insecticide acetamiprid (ACE) has been extensively studied in plants, animals, soils, and microbes. However, hydration of the N-cyanoimine group in ACE to the N-carbamoylimine derivate (IM-1-2) by purified microbes, the enzyme responsible for this biotransformation, and further degradation of IM-1-2 have not been studied. The present study used liquid chromatographymass spectrometry and nuclear magnetic resonance spectroscopy to determine that the nitrogen-fixing bacterium Ensifer meliloti CGMCC 7333 transforms ACE to IM-1-2. CGMCC 7333 cells degraded 65.1% of ACE in 96 h, with a half-life of 2.6 days. Escherichia coli Rosetta (DE3) overexpressing the nitrile hydratase (NHase) from CGMCC 7333 and purified NHase converted ACE to IM-1-2 with degradation ratios of 97.1% in 100 min and 93.9% in 120 min, respectively. Interestingly, IM-1-2 was not further degraded by CGMCC 7333, whereas it was spontaneously hydrolyzed at the N-carbamoylimine group to the derivate ACE-NH2, which was further converted to the derivative ACE-NH2. Then, ACE-NH2 was cleaved to the major metabolite IM-1-4. IM-1-2 showed significantly lower insecticidal activity than ACE against the aphid Aphis craccivora Koch. The present findings will improve the understanding of the environmental fate of ACE and the corresponding enzymatic mechanisms of degradation.