Triallate sulfoxide | 71133-38-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: Triallate sulfoxide
• 英文别名: N,N-di(propan-2-yl)-1-(2,3,3-trichloroprop-2-enylsulfinyl)formamide
• CAS: 71133-38-5
• 化学式: C₁₀H₁₆Cl₃NO₂S
• 分子量: 320.668
• InChiKey: ZUDLDAMMJGEFJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  56.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  野麦畏 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 Triallate sulfoxide
  参考文献：
  名称：

  [2,3] Sigmatropic rearrangement of -(3-chloroallyl) thiocarbamate sulfoxides followed by a 1,2-elimination reaction yielding unsaturated aldehydes and acid chlorides

  摘要：

  DOI：

  10.1016/s0040-4039(01)93566-x

文献信息

• [2,3] Sigmatropic rearrangement of -(3-chloroallyl) thiocarbamate sulfoxides followed by a 1,2-elimination reaction yielding unsaturated aldehydes and acid chlorides
  作者：Ingolf Schuphan、John E. Casida

  DOI：10.1016/s0040-4039(01)93566-x

  日期：1979.1
• Fatty acid and wax biosynthesis in susceptible and triallate-resistant<i>Avena fatua</i>L.
  作者：Anthony J. Kern、Larry L. Jackson、William E. Dyer

  DOI：10.1002/(sici)1096-9063(199709)51:1<21::aid-ps591>3.0.co;2-9

  日期：1997.9

  The recent characterization of triallate-resistant lines of wild oat (Avena fatua L.) deficient in triallate sulfoxidation provides an experimental system to investigate and differentiate the effects of triallate and triallate sulfoxide on wax and lipid biosynthesis. Greenhouse applications of triallate dramatically reduced epicuticular wax deposition in susceptible (S) but not resistant (R) wild oats. Triallate treatment had no effect on in-vivo concentrations of C-12 to C-26 fatty acids and fatty alcohols in R plants, while elongated fatty acid fractions (C > 18) were significantly reduced in S plants. In contrast, treatment with triallate sulfoxide reduced in-vivo concentrations of elongated fatty acids equally in R and S, supporting the hypothesis that triallate sulfoxide is more inhibitory than triallate towards fatty acid elongases. Although de-novo synthesis of short-chain fatty acids was not affected by triallate or triallate sulfoxide in R or S plants, synthesis of elongated fatty acid fractions was dramatically reduced in S plants by triallate. Fatty acid biosynthesis in R and S plants was equally sensitive to triallate sulfoxide. The results support the idea that in-vivo triallate sulfoxidation is necessary for herbicidal activity, and confirm that reduced rates of triallate sulfoxidation confer resistance in R wild oats.