(2,3,4,5,6-pentafluorophenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,3,4,5,6-pentafluorophenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• 化学式: C₁₅H₁₁Cl₂F₅O₂
• 分子量: 389.149
• InChiKey: YATDSXRLIUJOQN-HTRCEHHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(2,2-二氯乙烯基)-2,2-二甲基环丙烷羧酸甲酯 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 反应 3.0h， 生成 (2,3,4,5,6-pentafluorophenyl)methyl (1S,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Biological Activity of Pyrethroid Analogs in Pyrethroid-Susceptible and -Resistant Tobacco Budworms, Heliothis virescens (F.)

  摘要：

  The phenoxybenzyl moiety of conventional pyrethroids is a major site of oxidative metabolism in resistant tobacco budworms, Heliothis virescens (F.). In this study, this group was replaced with known P450 monooxygenase-inhibiting or oxidatively blocked groups. A variety of isomers (1R/1S, cis/trans) of the resulting chrysanthemates were tested as insecticides or synergists against tobacco budworms that were insecticide-susceptible (LSU) or that expressed metabolic resistance to cypermethrin (Pyr-R). A number of compounds with pentafluorophenyl, methylenedioxyphenyl, and propargyloxyphenyl groups were insecticidal, and activity was dependent on both geometric and stereochemical configuration of the acid moiety. Both traits and cis isomers of 1(R)-fenfluthrin, which contains a pentafluorophenyl group, suppressed resistance to cypermethrin in Pyr-R insects, confirming that oxidative metabolism of the phenoxybenzyl moiety is a major mechanism of resistance in this strain. Of the methylenedioxyphenyl compounds, 1R, trans, and cis isomers were tome and partially suppressed resistance in Pyr-R larvae. Similarly, both trans and cis isomers of alpha(S),1(R)-propargyloxyphenyl-containing compounds were insecticidal. Finally, alpha(R),1(R)-cis-methylenedioxyphenyl- and -propargyloxyphenyl-containing compounds were nontoxic but significantly enhanced toxicity of cypermethrin.

  DOI：

  10.1021/jf970408o

文献信息

• Biological Activity of Pyrethroid Analogs in Pyrethroid-Susceptible and -Resistant Tobacco Budworms, <i>Heliothis virescens </i>(F.)
  作者：Guomin Shan、Robert P. Hammer、James A. Ottea

  DOI：10.1021/jf970408o

  日期：1997.11.1

  The phenoxybenzyl moiety of conventional pyrethroids is a major site of oxidative metabolism in resistant tobacco budworms, Heliothis virescens (F.). In this study, this group was replaced with known P450 monooxygenase-inhibiting or oxidatively blocked groups. A variety of isomers (1R/1S, cis/trans) of the resulting chrysanthemates were tested as insecticides or synergists against tobacco budworms that were insecticide-susceptible (LSU) or that expressed metabolic resistance to cypermethrin (Pyr-R). A number of compounds with pentafluorophenyl, methylenedioxyphenyl, and propargyloxyphenyl groups were insecticidal, and activity was dependent on both geometric and stereochemical configuration of the acid moiety. Both traits and cis isomers of 1(R)-fenfluthrin, which contains a pentafluorophenyl group, suppressed resistance to cypermethrin in Pyr-R insects, confirming that oxidative metabolism of the phenoxybenzyl moiety is a major mechanism of resistance in this strain. Of the methylenedioxyphenyl compounds, 1R, trans, and cis isomers were tome and partially suppressed resistance in Pyr-R larvae. Similarly, both trans and cis isomers of alpha(S),1(R)-propargyloxyphenyl-containing compounds were insecticidal. Finally, alpha(R),1(R)-cis-methylenedioxyphenyl- and -propargyloxyphenyl-containing compounds were nontoxic but significantly enhanced toxicity of cypermethrin.