四溴菊酯 | 66841-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 四溴菊酯
• 英文名称: beta-cypermethrin
• 英文别名: cypermethrin；β-cypermethrin；1R-trans-αR-cypermethrin；[(R)-cyano-(3-phenoxyphenyl)methyl] (1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 66841-24-5
• 化学式: C₂₂H₁₉Cl₂NO₃
• 分子量: 416.304
• InChiKey: KAATUXNTWXVJKI-HBFSDRIKSA-N

物化性质

• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)
• 颜色/状态：
  Viscous yellowish brown semisolid mass.
• 熔点：
  81.3333333333 °C
• 溶解度：
  In acetone 620, dichloromethane 550, cyclohexane 515, ethyl acetate 440, chlorobenzene 420, acetophenone 390, o-xylene 350, hexane 7 (all in g/l, 25 °C). In maize oil 19-20, ethylene glycol <1 (both in g/kg at 20 °C).
• 蒸汽压力：
  1.73X10-5 mm Hg @ 20 °C
• 稳定性/保质期：
  Very stable in neutral and acidic media. Hydrolyzed in strongly alkaline media. Thermally stable up to 220 °C. Field data indicate that in practice it is stable to air and light.

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四溴菊酯 以 甲醇 为溶剂， 反应 192.0h， 生成 trans-cypermethrin
  参考文献：
  名称：

  Epimerization of Cypermethrin Stereoisomers in Alcohols

  摘要：

  Isomerization induced by light, heat, and organic solvents has been shown to occur for some pyrethroid insecticides. Alcohols are popular solvents that are used in sample extraction, storage, and analysis. Thus, alcohol-induced epimerization may contribute to the incorrect interpretation of results from enantioselective chemical analysis and bioassay of pyrethroids like cypermethrin. In this study, we investigated the relationship between the rate of epimerization of cypermethrin stereoisomers: 1R-cis-alpha R and 1R-trans-alpha R and short-chain alkyl alcohol properties. In this study, complete epimerization of 1R-cis-alpha R produced an almost equal fraction of 1R-cis-alpha S, and that of 1R-trans-alpha R yielded 1R-trans-alpha R For both stereoisomers, epimerization was most rapid in ethanol. The same stereoisomers underwent relatively rapid epimerization in methanol, n-propanol, 2-methyl-1-propanol, and n-butanol but were stable in 2-butanol, suggesting that secondary alcohols have reduced reactivity, likely due to steric hindrance. We further evaluated epimerization of 1R-cis-alpha R and 1R-trans-alpha R stereoisomers of cypermethrin as a function of water content in methanol. The presence of water in methanol generally increased the epimerization rate. For 1R-cis-alpha R, epimerization was most rapid with a water content of <= 2%, while for 1R-trans-alpha R, epimerization was most rapid with a water content of 10%. Results from this study clearly show that contact with commonly used primary alcohols may result in rapid abiotic epimerization, underscoring the importance of considering configurational stability in ensuring the analytical integrity and correct interpretation of bioassay data for stereoisomers of cypermethrin and similar pyrethroids.

  DOI：

  10.1021/jf900921g
• 作为产物：
  描述：

  trans-cypermethrin 以 水 、 丙酮 为溶剂， 生成 四溴菊酯
  参考文献：
  名称：

  合成拟除虫菊酯杀虫剂的手性稳定性。

  摘要：

  合成拟除虫菊酯是由多种立体异构体组成的手性化合物。对环境命运和生态毒性中对映选择性的评估需要在分析过程中保留立体异构体完整性的分析方法。在这项研究中，我们通过气相色谱（GC）分析和样品表征了四种常用拟除虫菊酯（顺式联苯菊酯（cis-BF），氯菊酯（PM），氯氰菊酯（CP）和氯氟氰菊酯（CF））的立体异构体的稳定性。准备。发现顺式-BF和PM的立体异构体是稳定的，而CP和CF的立体异构体在加热或水中不稳定。异构体转化仅发生在CP或CF的alphaC处，导致分析物立体异构体转化为差向异构体。在260°C的GC入口温度下，CP和CF的转化率约为9％。在有机溶剂和无菌水中，顺式-BF和PM的立体异构体是稳定的，但在室温下水中的CP和CF观察到缓慢的异构体转化。但是，当GC进样口温度保持在<或= 180℃或使用柱上进样时，CP和CF的异构体转化率相对较小（2-3％）。水中αC的异构体转化表明，非生物

  DOI：

  10.1021/jf048425i

文献信息

• Fluorometric assay of cyanophoric pyrethroids based on benzothiazole modified carbon quantum dots
  作者：Peng Wang、Qiang Zhang、Donghui Liu、Zhiqiang Zhou、Peng Wang

  DOI：10.1039/d3nj00465a

  日期：——

  A fluorometric assay based on benzothiazole carbon quantum dots (benzothiazole-CDs) was developed for the determination of cyanophoric pyrethroids (CPs, e.g., cypermethrin, deltamethrin and fenpropathrin).

  开发了一种基于苯并噻唑碳量子点（benzothiazole-CDs）的荧光测定法，用于测定氰戊菊酯（CPs，例如氯氰菊酯、溴氰菊酯和氰戊菊酯）。
• Abiotic Enantiomerization of Permethrin and Cypermethrin:  Effects of Organic Solvents
  作者：Sujie Qin、Jianying Gan

  DOI：10.1021/jf0708894

  日期：2007.7.1

  All synthetic pyrethroids are chiral compounds, and isomerization has been frequently observed from exposure to certain solvents. However, so far, pyrethroid isomerization caused by solvents has not been characterized at the enantiomer level. In this study, we evaluated the occurrence of enantiomerization of two commonly used pyrethroids, permethrin and cypermethrin, in various organic solvents and solvent-water systems. The four stereoisomers of permethrin were stable under all test conditions. Rapid enantiomerization of cypermethrin was observed in isopropanol and methanol but not in n-hexane, acetone, or methylene chloride. After 4 days at room temperature, 18-39% conversions occurred for the different cypermethrin stereoisomers in isopropanol and methanol, and the enantiomerization invariably took place at the alpha-carbon position. The extent of enantiomerization was affected by temperature dependence and was also influenced by water as a cosolvent. In solvent-water mixtures, cypermethrin underwent gradual enantiomerization in acetone-water and rapid enantiomerization in isopropanol-water or methanol-water. The extent of enantiomerization varied among the solvents and as a function of the solvent-to-water ratio. Results from this study suggest that exposure to certain solvents and water may cause artifacts in chiral analysis and that for isomer-enriched pyrethroid products, such abiotic enantiomerization may render the products less effective because the conversion leads to the formation of inactive stereoisomers.
• CONVERSION OF PYRETHROID ISOMERS TO MORE ACTIVE SPECIES
  申请人：FMC Corporation

  公开号：EP0363428A1

  公开（公告）日：1990-04-18
• Methods and compositions for increasing the efficacy of biologically-active ingredients
  申请人：Windsor Brian J.

  公开号：US20060276339A1

  公开（公告）日：2006-12-07

  The invention provides methods and compositions for modulating the sensitivity of cells to cytotoxic compounds and other active agents. In accordance with the invention, compositions are provided comprising combinations of ectophosphatase inhibitors and active agents. Active agents include antibiotics, fungicides, herbicides, insecticides, chemotherapeutic agents, and plant growth regulators. By increasing the efficacy of active agents, the invention allows use of compositions with lowered concentrations of active ingredients.
• US4224227A
  申请人：——

  公开号：US4224227A

  公开（公告）日：1980-09-23