(R)-isocarbophos

• 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: (R)-isocarbophos
• 英文别名: (-)-isocarbophos；propan-2-yl 2-[amino(methoxy)phosphinothioyl]oxybenzoate
• 化学式: C₁₁H₁₆NO₄PS
• 分子量: 289.292
• InChiKey: YFVOXLJXJBQDEF-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-isocarbophos 在 calcium 作用下， 反应 3.0h， 生成 水杨酸异丙酯
  参考文献：
  名称：

  南通铜杯X1 T中有机磷杀虫剂异卡波菲的对映选择性降解：特征，对映选择性调控，降解途径和毒性评估

  摘要：

  手性农药对映异构体通常显示出选择性功效和非目标毒性。本研究系统地研究了南通铜杯X1 T对手性有机磷杀虫剂异卡波菲（ICP）的对映选择性降解特性。菌株X1 T比S异构体（S -ICP）优先降解ICP R异构体（R -ICP ）。R -ICP的降解速率常数比S -ICP的降解速率常数高42倍，而前者对害虫的生物活性较弱，但对人的毒性却比后者高。S -ICP与R的浓度比-ICP确定S- ICP是否可以被X1 T菌株降解。只有当比率（C S -ICP / C R -ICP）大于62时，S- ICP才开始降解。二价金属阳离子可以提高X1 T菌株的降解能力。鉴定出的检测到的代谢产物提示了一种新的水解途径，而水解产物对鱼类和绿藻的毒性比PO键断裂的代谢产物低。粗酶以相似的速率降解了R- ICP和S- ICP，表明对映选择性降解是由于X1 T菌株的运输。菌株X1T还可以对映选择性地降解手性有机磷杀虫剂异苯磷甲基和丙苯磷。X1

  DOI：

  10.1016/j.jhazmat.2021.126024
• 作为产物：
  描述：

  水胺硫磷 在 Chiralcel OD column 作用下， 生成 (R)-isocarbophos 、 (R)-isocarbophos
  参考文献：
  名称：

  Single and Joint Acute Toxicity of Isocarbophos Enantiomers to Daphnia magna

  摘要：

  Although enantioselectivity in the toxicity of chiral pesticides has received considerable attention over recent years, how coexisting enantiomers interact with each other during their toxic action remains unknown. In this study, we attempted to resolve the enantiomers of a chiral organophosphate insecticide, isocarbophos, and investigated the acute toxicity of individual enantiomers and various enantiomer mixtures. Baseline enantiomeric separation of isocarbophos was achieved on a Chiralcel OD column with the mobile phase of n-hexane/isopropanol (90/10, v/v) at a flow rate of 0.8 mL/min. The resolved enantiomers were differentiated by their responses on a circular dichroism detector. The median lethal concentrations (LC50) of racemate, (+)-enantiomer, and (-)-enantiomer of isocarbophos toward Daphnia magna were 13.9, 7.08, and 353 mu g/L, respectively, after 48 h of static exposure, displaying a 50-fold difference between the enantiomers. Toxic unit (TU) analysis was employed to evaluate the joint toxicity of isocarbophos enantiomer mixtures. The calculated TUmix for the acute toxicity (48 h test) of various binary mixtures ranged from 0.83 to 1.04, suggesting a mode of additive effect. Further evaluation of available literature data for chiral organophosphorus insecticides showed that the joint toxicity of enantiomers may be additive, synergistic, and antagonistic. Therefore, when significant enantioselectivity exists for a chiral pesticide, it is important to also evaluate the interaction of enantiomers in the joint toxicity effect when enantiomers are present in a mixture.

  DOI：

  10.1021/jf073535l

文献信息

• Enantioselective degradation of the organophosphorus insecticide isocarbophos in Cupriavidus nantongensis X1T: Characteristics, enantioselective regulation, degradation pathways, and toxicity assessment
  作者：Liancheng Fang、Luyuan Xu、Nan Zhang、Qiongying Shi、Taozhong Shi、Xin Ma、Xiangwei Wu、Qing X. Li、Rimao Hua

  DOI：10.1016/j.jhazmat.2021.126024

  日期：2021.9

  hydrolysis pathway, while the hydrolytic metabolites were less toxic to fish and green algae than those from P-O bond breakage. The crude enzyme degraded both R-ICP and S-ICP in a similar rate, indicating that enantioselective degradation was due to the transportation of strain X1T. The strain X1T also enantioselectively degraded the chiral organophosphorus insecticides isofenphos-methyl and profenofos

  手性农药对映异构体通常显示出选择性功效和非目标毒性。本研究系统地研究了南通铜杯X1 T对手性有机磷杀虫剂异卡波菲（ICP）的对映选择性降解特性。菌株X1 T比S异构体（S -ICP）优先降解ICP R异构体（R -ICP ）。R -ICP的降解速率常数比S -ICP的降解速率常数高42倍，而前者对害虫的生物活性较弱，但对人的毒性却比后者高。S -ICP与R的浓度比-ICP确定S- ICP是否可以被X1 T菌株降解。只有当比率（C S -ICP / C R -ICP）大于62时，S- ICP才开始降解。二价金属阳离子可以提高X1 T菌株的降解能力。鉴定出的检测到的代谢产物提示了一种新的水解途径，而水解产物对鱼类和绿藻的毒性比PO键断裂的代谢产物低。粗酶以相似的速率降解了R- ICP和S- ICP，表明对映选择性降解是由于X1 T菌株的运输。菌株X1T还可以对映选择性地降解手性有机磷杀虫剂异苯磷甲基和丙苯磷。X1
• Single and Joint Acute Toxicity of Isocarbophos Enantiomers to <i>Daphnia magna</i>
  作者：Kunde Lin、Weiping Liu、Ling Li、Jay Gan

  DOI：10.1021/jf073535l

  日期：2008.6.1

  Although enantioselectivity in the toxicity of chiral pesticides has received considerable attention over recent years, how coexisting enantiomers interact with each other during their toxic action remains unknown. In this study, we attempted to resolve the enantiomers of a chiral organophosphate insecticide, isocarbophos, and investigated the acute toxicity of individual enantiomers and various enantiomer mixtures. Baseline enantiomeric separation of isocarbophos was achieved on a Chiralcel OD column with the mobile phase of n-hexane/isopropanol (90/10, v/v) at a flow rate of 0.8 mL/min. The resolved enantiomers were differentiated by their responses on a circular dichroism detector. The median lethal concentrations (LC50) of racemate, (+)-enantiomer, and (-)-enantiomer of isocarbophos toward Daphnia magna were 13.9, 7.08, and 353 mu g/L, respectively, after 48 h of static exposure, displaying a 50-fold difference between the enantiomers. Toxic unit (TU) analysis was employed to evaluate the joint toxicity of isocarbophos enantiomer mixtures. The calculated TUmix for the acute toxicity (48 h test) of various binary mixtures ranged from 0.83 to 1.04, suggesting a mode of additive effect. Further evaluation of available literature data for chiral organophosphorus insecticides showed that the joint toxicity of enantiomers may be additive, synergistic, and antagonistic. Therefore, when significant enantioselectivity exists for a chiral pesticide, it is important to also evaluate the interaction of enantiomers in the joint toxicity effect when enantiomers are present in a mixture.