(2E,4Z)-N-decadienoylpyrrolidine | 1244783-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2E,4Z)-N-decadienoylpyrrolidine
• 英文别名: (2E,4Z-decadienoyl)pyrrolidine；(2E,4Z)-1-(pyrrolidin-1-yl)deca-2,4-dien-1-one；(2E,4Z)-1-pyrrolidin-1-yldeca-2,4-dien-1-one
• CAS: 1244783-85-4
• 化学式: C₁₄H₂₃NO
• 分子量: 221.343
• InChiKey: BFZBGTMIBOQWBA-BQGCWICQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 (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 (2E,4Z)-N-decadienoylpyrrolidine
  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
• HERBICIDAL COMPOSITION AND METHOD OF USE THEREOF
  申请人：Syngenta Participations AG

  公开号：EP2967044A1

  公开（公告）日：2016-01-20
• Use of Sarmentine and Its Analogues With an Herbicide, and Compositions Thereof
  申请人：MARRONE BIO INNOVATIONS, INC.

  公开号：US20160212999A1

  公开（公告）日：2016-07-28

  Disclosed herein are methods for modulating (e.g., inhibiting) emergence and growth of monocotyledonous or dicotyledonous plants (e.g., weeds and grasses) using sarmentine and/or a sarmentine analogue and a second herbicide. The application of sarmentine and/or a sarmentine analogue with a second herbicide to a plant and/or its growth substrate results in a synergistic pre- and/or post-emergence herbicidal activity against the plant. The present method also provides compositions comprising sarmentine and/or a sarmentine analogue, in combination with a second herbicide.