4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid | 31183-15-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid
• CAS: 31183-15-0
• 化学式: C₁₄H₁₁NO₃
• mdl: MFCD00627801
• 分子量: 241.246
• InChiKey: MJBXLSQXZHYTSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid 在 sodium acetate 、 乙酸酐 作用下， 反应 2.0h， 生成 1-(2-萘)-1H-吡咯-2,5-二酮
  参考文献：
  名称：

  Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

  摘要：

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

  DOI：

  10.1021/acs.jafc.6b02250
• 作为产物：
  描述：

  马来酸酐 、 2-萘胺 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-(naphthalen-2-ylamino)-4-oxobut-2-enoic acid
  参考文献：
  名称：

  Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

  摘要：

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

  DOI：

  10.1021/acs.jafc.6b02250

文献信息

• US4127617A
  申请人：——

  公开号：US4127617A

  公开（公告）日：1978-11-28
• Potent Nematicidal Activity of Maleimide Derivatives on <i>Meloidogyne incognita</i>
  作者：Kodjo Eloh、Monica Demurtas、Manuel Giacomo Mura、Alessandro Deplano、Valentina Onnis、Nicola Sasanelli、Andrea Maxia、Pierluigi Caboni

  DOI：10.1021/acs.jafc.6b02250

  日期：2016.6.22

  Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 +/- 1.3, 5.1 +/- 3.4, 16.2 +/- 5.4, and 19.0 +/- 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 +/- 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at SO mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.