N-cyclopentyl-2E,4Z-decadienamide | 1244783-84-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-cyclopentyl-2E,4Z-decadienamide
• 英文别名: (2E,4Z)-N-cyclopentyldeca-2,4-dienamide
• CAS: 1244783-84-3
• 化学式: C₁₅H₂₅NO
• 分子量: 235.37
• InChiKey: XRPSXCHMKDNUFL-ONVRAGQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  环戊胺 、 (2E,4Z)-deca-2,4-dienamide 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 N-cyclopentyl-2E,4Z-decadienamide
  参考文献：
  名称：

  Phytotoxicity of Sarmentine Isolated from Long Pepper (Piper longum) Fruit

  摘要：

  Discovery of novel natural herbicides has become crucial to overcome increasing weed resistance and environmental issues. In this article, we describe the finding that a methanol extract of dry long pepper (Piper longum L.) fruits is phytotoxic to lettuce (Lactuca sativa L.) seedlings. The bioassay-guided fractionation and purification of the crude extract led to isolation of sarmentine (1), a known compound, as the active principle. Phytotoxicity of 1 was examined with a variety of seedlings of field crops and weeds. Results indicated that 1 was a contact herbicide and possessed broad-spectrum herbicidal activity. Moreover, a series of sarmentine analogues were then synthesized to study the structure-activity relationship (SAR). SAR studies suggested that phytotoxicity of sarmentine and its analogues was specific due to chemical structures, i.e., the analogues of the acid moiety of 1 were active, but the amine and its analogues were inactive; the ester analogues and amide analogues with a primary amine of 1 were also inactive. In addition, quantification of 1 from different resources of the dry P. longum fruits using liquid chromatography-mass spectrometry showed a wide variation, ranging from almost zero to 0.57%. This study suggests that 1 has potential as an active lead molecule for synthesized herbicides as well as for bioherbicides derived from natural resources.

  DOI：

  10.1021/jf102087c

文献信息

• USE OF SARMENTINE AND ITS ANALOGS FOR CONTROLLING PLANT PESTS
  申请人：Huang Huazhang

  公开号：US20110021358A1

  公开（公告）日：2011-01-27

  Methods and compositions for controlling plant pests, particularly weeds and/or plant phytopathogens using sarmentine and/or analogs thereof are disclosed.

  揭示了利用沙曼汀和/或其类似物控制植物害虫，特别是杂草和/或植物病原体的方法和组合物。
• Use of sarmentine and its analogs for controlling plant pests
  申请人：Marrone Bio Innovations, Inc.

  公开号：EP2710892A2

  公开（公告）日：2014-03-26

  Methods and compositions for controlling plant pests, particularly weeds and/or plant phytopathogens using sarmentine and/or analogs thereof are disclosed.

  本发明公开了使用沙门菌素和/或其类似物控制植物害虫，特别是杂草和/或植物病原体的方法和组合物。
• Use of sarmentine and its analogs for controlling weeds
  申请人：Marrone Bio Innovations, Inc.

  公开号：EP2710892B1

  公开（公告）日：2016-12-14
• US8466192B2
  申请人：——

  公开号：US8466192B2

  公开（公告）日：2013-06-18
• US8957000B2
  申请人：——

  公开号：US8957000B2

  公开（公告）日：2015-02-17