顺式氯菊酯 | 61949-76-6

• 物质功能分类: 化学农药原药 - 杀虫剂 - 有机氯杀虫剂
• 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: 顺式氯菊酯
• 英文名称: Eksmin
• 英文别名: (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate；cis-(-)-3'-phenoxybenzyl-3-(2',2'-dichlorovinyl)-2,2-dimethyl-cyclopropane carboxylate；3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate；¹⁴C-cis-permethrin；1R-(-)-cis-permethrin；(R)-cis-permethrin；cis-Permethrin；(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 61949-76-6；54774-45-7
• 化学式: C₂₁H₂₀Cl₂O₃
• 分子量: 391.294
• InChiKey: RLLPVAHGXHCWKJ-HKUYNNGSSA-N

物化性质

• 熔点：
  63～65℃
• 沸点：
  505.74°C (rough estimate)
• 密度：
  1.1531 (rough estimate)
• 闪点：
  -18 °C
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）
• 物理描述：
  YELLOW-BROWN-TO-BROWN VISCOUS LIQUID OR CRYSTALS.
• 蒸汽压力：
  Vapor pressure, Pa at 20 °C:
• 保留指数：
  2615;2662;2616.5;2609.3;2636.7;2615

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn,F,N
• 安全说明：
  S13,S16,S24,S36/37/39,S60,S61,S62
• 危险类别码：
  R67,R38,R43,R20/22,R50/53,R11,R65
• WGK Germany：
  2,3
• 海关编码：
  2916209090
• 危险品运输编号：
  UN 1145 3/PG 2

制备方法与用途

用途

顺式-氯菊酯标准溶液主要应用于农药残留分析、环境监测及质量控制等领域。作为一种分析标准，它能够确保实验结果的准确性和可靠性。

反应信息

• 作为反应物：
  描述：

  顺式氯菊酯 、 chlorozinc(1+),2H-furan-2-ide 以87%的产率得到
  参考文献：
  名称：

  MINATO, AKIO, J. ORG. CHEM., 56,(1991) N2, C. 4052-4056

  摘要：

  DOI：
• 作为产物：
  描述：

  4,7,7-trimethylbicyclo[4.1.0]hept-3-en-2-one 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 六甲基磷酰三胺 、 sodium hydroxide 、 potassium permanganate 、 三乙胺 、 3-氯苯甲酸 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 正戊烷 为溶剂， 反应 97.0h， 生成 顺式氯菊酯
  参考文献：
  名称：

  从（+）-3-care合成（1r）-顺-（-）-氯菊酯，（1r）-顺-（+）-氯氰菊酯和（1r）-顺-（+）-溴氰菊酯（癸）的新合成路线

  摘要：

  从（+）-3-carene（5）容易获得的（+）-4α-乙酰基-2-carene（6）被转化为（1R）-cis-（+）-3-（2'，2 （11）和（22）的11个步骤中的'-（二卤代戊酰基）-2、2-二甲基-环丙烷-1-羧酸（21）和（22）的总收率分别为23％和14％。或者，将（+）-3-烯烃（5）的氧化产物（-）-5-酮-3-烯烃（23）在五次转化为（1R）-顺式-（-）-氯菊酯（1）步骤，总收率为20％。在另一种灵活的方法中，将（-）-（23）分为七个步骤，整体上分别转换为（1R）-顺式-（+）-（21）和（1R）-顺式-（+）-（22）产率分别为33％和23％。这些结果与文献报道有关将（1R）-顺式-（+）-（21）和（22）转化为（1R）-顺式-（-）-（1），

  DOI：

  10.1016/s0040-4020(01)88177-1

文献信息

• Assignment of absolute configurations of permethrin and its synthon 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid by electronic circular dichroism, optical rotation, and X-ray crystallography
  作者：Wolfgang Bicker、Karol Kacprzak、Marcin Kwit、Michael Lämmerhofer、Jacek Gawronski、Wolfgang Lindner

  DOI：10.1016/j.tetasy.2009.03.035

  日期：2009.5

  3-phenoxybenzyl alcohol yielded PM. Electronic circular dichroism (ECD) spectra of DCCA and PM stereoisomers were measured in non-polar (cyclohexane containing 5% v/v 1,2-dichloroethane) and non-protic polar (acetonitrile) solvents. Cotton effects suitable to distinguish the four stereoisomers of each DCCA and PM were obtained. Absolute configurations of DCCA were determined by confrontation of calculated

  生物/毒理学相关手性化合物（如拟除虫菊酯型杀虫剂氯菊酯（PM））的单一立体异构体的可用性以及其绝对构型的可靠测定对于详细研究和正确选择立体选择效应至关重要。在这种情况下，从所有四种立体异构体的对映异构体混合物中分离出3-（2,2-二氯乙烯基）-2,2-二甲基环丙烷羧酸（DCCA），PM的前体，代谢产物和环境降解产物的单一立体异构体通过第一步色谱中的非对映选择性反相分离与第二步中的直接对映异构体分离相结合的两步色谱法，获得了> 99％的过量残留物。用3-苯氧基苄醇酯化DCCA立体异构体得到PM。在非极性（含有5％v / v 1,2-二氯乙烷的环己烷）和非质子极性（乙腈）溶剂中测量DCCA和PM立体异构体的电子圆二色性（ECD）光谱。获得了适合区分每种DCCA和PM的四种立体异构体的棉花效应。DCCA的绝对构型由计算值（使用B3LYP混合函数的时变密度泛函理论）和实验ECD和旋光（OR）数据的
• High concentration topical insecticides containing pyrethroids
  申请人：Cottrell W. Ian

  公开号：US20050245582A1

  公开（公告）日：2005-11-03

  A topical insecticide preparation is provided which can be safe to use and avoids many common deleterious side effects of conventional topical insecticides. The topical insecticide contains a combination of a first pyrethroid insecticide effective for killing fleas, a second pyrethroid insecticide effective for killing ticks, and an insect growth regulator (IGR). The topical insecticide preparation can be packaged together or packaged so that the first and second pyrethroid insecticides are stored separately prior to administration of the insecticide preparation to the animal. The combination of the first and second pyrethroid insecticides with an insect growth regulator results in an insecticide preparation formulated to have enhanced insecticidal activity against fleas and ticks compared to the effectiveness of the first and second insecticides used alone. Further, the combination of the first and second pyrethroid insecticides with an insect growth regulator produces an insecticide preparation having enhanced insecticidal activity against fleas and ticks while advantageously minimizing the total amount of insecticide needed for its effectiveness.

  提供了一种局部杀虫剂制剂，可以安全使用并避免许多常见的传统局部杀虫剂的有害副作用。该局部杀虫剂包含第一种对杀灭跳蚤有效的拟除虫菊酯类杀虫剂，第二种对杀灭蜱有效的拟除虫菊酯类杀虫剂和昆虫生长调节剂（IGR）。该局部杀虫剂制剂可以一起包装或分开包装，以便在给动物施用杀虫剂制剂之前将第一种和第二种拟除虫菊酯类杀虫剂分别存储。第一种和第二种拟除虫菊酯类杀虫剂与昆虫生长调节剂的组合使得该杀虫剂制剂具有比单独使用第一种和第二种杀虫剂更强的杀灭跳蚤和蜱的杀虫活性。此外，第一种和第二种拟除虫菊酯类杀虫剂与昆虫生长调节剂的组合在优化杀虫效果的同时，有利于最小化所需杀虫剂的总量。
• HIGH CONCENTRATION TOPICAL INSECTICIES CONTAINING PYRETHROIDS
  申请人：Cottrell Ian

  公开号：US20070276014A1

  公开（公告）日：2007-11-29

  A topical insecticide preparation is provided which can be safe to use and avoids many common deleterious side effects of conventional topical insecticides. The topical insecticide contains a combination of a first pyrethroid insecticide effective for killing fleas, a second pyrethroid insecticide effective for killing ticks, and an insect growth regulator (IGR). The topical insecticide preparation can be packaged together or packaged so that the first and second pyrethroid insecticides are stored separately prior to administration of the insecticide preparation to the animal. The combination of the first and second pyrethroid insecticides with an insect growth regulator results in an insecticide preparation formulated to have enhanced insecticidal activity against fleas and ticks compared to the effectiveness of the first and second insecticides used alone. Further, the combination of the first and second pyrethroid insecticides with an insect growth regulator produces an insecticide preparation having enhanced insecticidal activity against fleas and ticks while advantageously minimizing the total amount of insecticide needed for its effectiveness.

  提供了一种局部杀虫剂制剂，可以安全使用，并避免许多传统局部杀虫剂的常见有害副作用。该局部杀虫剂包含第一种杀灭跳蚤有效的拟除虫菊酯杀虫剂，第二种杀灭蜱有效的拟除虫菊酯杀虫剂和昆虫生长调节剂（IGR）。该局部杀虫剂制剂可以一起包装或分开包装，以便在给动物施用杀虫剂制剂之前分别存储第一和第二种拟除虫菊酯杀虫剂。第一和第二种拟除虫菊酯杀虫剂与昆虫生长调节剂的组合导致杀虫剂制剂具有比单独使用第一和第二种杀虫剂更强的杀虫活性，可以增强对跳蚤和蜱的杀虫活性。此外，第一和第二种拟除虫菊酯杀虫剂与昆虫生长调节剂的组合产生的杀虫剂制剂在优化杀虫效果的同时，有利于最小化所需杀虫剂的总量。
• HIGH CONCENTRATION TOPICAL INSECTICIDES CONTAINING PYRETHROIDS
  申请人：Cottrell Ian

  公开号：US20110144166A1

  公开（公告）日：2011-06-16

  A topical insecticide preparation is provided which can be safe to use and avoids many common deleterious side effects of conventional topical insecticides. The topical insecticide contains a combination of a first pyrethroid insecticide effective for killing fleas, a second pyrethroid insecticide effective for killing ticks, and an insect growth regulator (IGR). The topical insecticide preparation can be packaged together or packaged so that the first and second pyrethroid insecticides are stored separately prior to administration of the insecticide preparation to the animal. The combination of the first and second pyrethroid insecticides with an insect growth regulator results in an insecticide preparation formulated to have enhanced insecticidal activity against fleas and ticks compared to the effectiveness of the first and second insecticides used alone. Further, the combination of the first and second pyrethroid insecticides with an insect growth regulator produces an insecticide preparation having enhanced insecticidal activity against fleas and ticks while advantageously minimizing the total amount of insecticide needed for its effectiveness.

  提供了一种局部杀虫剂制剂，可以安全使用并避免许多常见的传统局部杀虫剂的有害副作用。该局部杀虫剂包含第一种对杀灭跳蚤有效的拟除虫菊酯杀虫剂、第二种对杀灭蜱有效的拟除虫菊酯杀虫剂和昆虫生长调节剂（IGR）。该局部杀虫剂制剂可以一起包装或分开包装，以便在给动物施用杀虫剂制剂之前将第一和第二种拟除虫菊酯杀虫剂分别存储。第一和第二种拟除虫菊酯杀虫剂与昆虫生长调节剂的组合使得该杀虫剂制剂在杀灭跳蚤和蜱方面具有比单独使用第一和第二种杀虫剂更强的杀虫活性。此外，第一和第二种拟除虫菊酯杀虫剂与昆虫生长调节剂的组合产生的杀虫剂制剂在最小化其有效性所需的总杀虫剂量的同时，对杀灭跳蚤和蜱具有增强的杀虫活性。
• PROCESS FOR PREPARATION OF STABLE, MICROENCAPSULATED AND SUSTAINED RELEASE BIOCIDAL ACTIVES AND COMPOSITION THEREOF
  申请人：Premachandran Raman

  公开号：US20120164203A1

  公开（公告）日：2012-06-28

  Disclosed herein is a process for the preparation of a stable sustained-release biocidal composition containing microencapsulated biocide and wherein the process comprises the steps of: (i) adsorbing the biocide onto an inert carrier by grinding to attain the required particle size and wherein the ratio of biocide; inert carrier is in the range of about 1:99 to about 99:1 (ii) optionally coating with an appropriate amine or imine compound or a water resistant film forming polymer and dispersing the resultant biocide encapsulated inert carrier in an aqueous medium in the presence of suitable dispersing agent (iii) adding at least one thickening agent to re-disperse the encapsulated biocide containing partial amount of non-encapsulated biocide if any and (iv) preparing an aqueous or solvent based sustained release biocide dispersion. Also disclosed is a stable, sustained-release biocidal composition prepared by such process and uses thereof.

  本文揭示了一种制备稳定的持续释放生物杀菌剂组合物的方法，其中包含微囊化生物杀菌剂，所述方法包括以下步骤：(i)通过研磨将生物杀菌剂吸附到惰性载体上，以达到所需的粒径，其中生物杀菌剂；惰性载体的比例在约1:99至约99:1的范围内；(ii)可选地用适当的胺或亚胺化合物或耐水膜形成聚合物进行包覆，并在适当的分散剂存在下将所得的生物杀菌剂微囊化惰性载体分散在水性介质中；(iii)添加至少一种增稠剂以重新分散含有任何非微囊化生物杀菌剂的微囊化生物杀菌剂，(iv)制备基于水性或溶剂的持续释放生物杀菌剂分散液。还揭示了通过这种方法制备的稳定的持续释放生物杀菌剂组合物及其用途。

表征谱图