1R-cis-αR-cypermethrin | 66290-21-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1R-cis-αR-cypermethrin
• 英文别名: alpha-Cyano-3-phenoxybenzyl (1R-(1alpha(R*),3alpha))-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate；[(R)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 66290-21-9；65731-83-1
• 化学式: C₂₂H₁₉Cl₂NO₃
• 分子量: 416.304
• InChiKey: KAATUXNTWXVJKI-BJLQDIEVSA-N

物化性质

• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

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：

  1R-cis-αR-cypermethrin 以 异丙醇 为溶剂， 生成 高效氯氰菊酯
  参考文献：
  名称：

  Abiotic Enantiomerization of Permethrin and Cypermethrin:  Effects of Organic Solvents

  摘要：

  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.

  DOI：

  10.1021/jf0708894
• 作为产物：
  描述：

  高效氯氰菊酯 以 水 、 丙酮 为溶剂， 生成 1R-cis-αR-cypermethrin
  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

• Verfahren zur Herstellung von optisch aktiven, in 3-Stellung substituierten 2-(2',2'-Dihalogenvinyl)-cyclopropan-1-carbonsäuren und deren Derivaten; 4-(2',2',2'-Trihalogenäthyl)-cyclobutan-1-sulfonsäuresalze und deren Herstellung
  申请人：CIBA-GEIGY AG

  公开号：EP0012722A1

  公开（公告）日：1980-06-25

  Es werden ein neues Verfahren zur Herstellung von optisch aktiven, in 3-Stellung substituierten 2-(2',2'-Dihalo- genvinyl)-cyclopropan-1-carbonsäuren und Derivaten davon sowie neue 4-(2',2',2'-Trihalogenäthyl)-cyclobutan-1-sulfonsäuresalze beschrieben. Dabei werden Racemate von bestimmten Cyclobutanonen entweder mit dem schwefligsauren Salz einer optisch aktiven Base oder in Gegenwart von Wasser und Schwefeldioxid mit einer optisch aktiven Base zu einem 4-(2',2',2'-Trihalogenäthyl)-cyclobutan-1-sulfonsäuresalz umgesetzt. Die erhaltenen reinen Diastereomeren werden entweder direkt in Gegenwart einer Base zu optisch aktiven 2-(2',2'-Dihalogenvinyl)-cyciopropan-1-carbonsäure(derivate)n umgesetzt, oder aber die reinen Diastereomeren werden zu optisch aktiven Cyclobutanonen zersetzt, worauf man diese in Gegenwart einer Base in die gewünschten optisch aktiven Cyclopropancarbonsäuren überführt, die zur Hauptsache in der cis-Konfiguration anfallen. Die erfindungsgemäß erhaltenen Cyclopropancarbonsäuren bzw. deren Derivate können zur Herstellung von Schädlingsbekämpfungsmitteln, besonders insektiziden, verwendet oder direkt als Schädlingsbekämpfungsmittel eingesetzt werden.

  描述了一种制备具有光学活性的、3-取代的 2-(2',2'-二卤乙烯基)-环丙烷-1-羧酸及其衍生物以及新的 4-(2',2',2'-三卤乙基)-环丁烷-1-磺酸盐的新工艺。某些环丁酮的外消旋体与光学活性碱的硫酸盐反应，或在水和二氧化硫存在下与光学活性碱反应，得到 4-(2',2',2'-三卤乙基)-环丁烷-1-磺酸盐。得到的纯非对映异构体要么在碱存在下直接转化为具有光学活性的 2-(2',2'-二卤乙烯基)-环丙烷-1-羧酸（衍生物），要么将纯非对映异构体分解为具有光学活性的环丁酮，然后这些环丁酮在碱存在下转化为所需的具有光学活性的环丙烷羧酸，这些环丙烷羧酸主要以顺式构型得到。根据本发明得到的环丙烷羧酸或其衍生物可用于生产杀虫剂，特别是杀虫剂，也可直接用作杀虫剂。
• Improved method for producing emulsifiable pesticide solutions
  申请人：Agriphar S.A.

  公开号：EP2548437A1

  公开（公告）日：2013-01-23

  The current invention provides a kit of parts for producing an emulsifiable pesticide solution comprising: (a) a water miscible organic solvent selected from the list of a glycol ether, a glycerol formal, dimethylsulfoxide, gamma-butyrolactone or mixtures thereof, (b) an alkoxylated alcohol with an average of 6 to 80 moles of ethylene oxide and 2 to 60 moles of propylene oxide per mole of alcohol; and (c) a pesticidal active ingredient. The invention further provides a composition for producing an emulsifiable pesticide solution, a method for producing such a composition and a method for treating an agricultural crop.

  本发明提供了一种生产可乳化农药溶液的部件套件，包括 (a) 可与水混溶的有机溶剂，选自乙二醇醚、甘油甲醛、二甲基亚砜、γ-丁内酯或其混合物、 (b) 烷氧基化醇，每摩尔醇平均含有 6 至 80 摩尔环氧乙烷和 2 至 60 摩尔环氧丙烷；以及 (c) 杀虫剂活性成分。 本发明进一步提供了一种生产可乳化农药溶液的组合物、一种生产这种组合物的方法和一种处理农作物的方法。
• Epimerization of Cypermethrin Stereoisomers in Alcohols
  作者：Mae Grace Nillos、Sujie Qin、Cynthia Larive、Daniel Schlenk、Jay Gan

  DOI：10.1021/jf900921g

  日期：2009.8.12

  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.
• KRAL, VLADIMIR;DVORAK, DALIMIL;ZAVADA, JIRI;STIBOR, IVAN;MOSTECKY, JIRI;V+
  作者：KRAL, VLADIMIR、DVORAK, DALIMIL、ZAVADA, JIRI、STIBOR, IVAN、MOSTECKY, JIRI、V+

  DOI：——

  日期：——
• SMELTZ, L. A.
  作者：SMELTZ, L. A.

  DOI：——

  日期：——