(S)-fipronil | 302578-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-fipronil
• 英文别名: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(S)-trifluoromethylsulfinyl]pyrazole-3-carbonitrile
• CAS: 302578-96-7
• 化学式: C₁₂H₄Cl₂F₆N₄OS
• 分子量: 437.152
• InChiKey: ZOCSXAVNDGMNBV-SANMLTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  11

ADMET

代谢

(+)-氟虫腈有人体已知代谢物，包括氟虫腈砜。

(+)-fipronil has known human metabolites that include fipronil sulfone.

来源:NORMAN Suspect List Exchange

反应信息

• 作为产物：
  描述：

  氟虫腈 在 amylose tris(3-chloro-5-methylphenylcarbamate) immobilized on 3 μm porous spherical silica particles 作用下， 以 水 、 乙腈 为溶剂， 生成 (S)-fipronil 、 (R)-fipronil
  参考文献：
  名称：

  杀虫剂氟虫腈对映体的手性拆分及其主要转化产物的高效液相色谱-质谱联用测定

  摘要：

  使用基于直链淀粉三（3-氯-5-甲基苯基氨基甲酸酯）的手性柱开发了一种高效液相色谱-质谱（HPLC-MS）方法，用于分析氟虫腈（一种流行的杀虫神经毒剂）和相关的转化产物. 优化后的方法达到了单次同时完全分离多种氟虫腈的目标，包括氟虫腈对映体、氟虫腈代谢物和光产物的手性分离。这种方法的有效性通过其在分析暴露于阳光条件下的一系列氟虫腈样品中的应用得到证明。笼统，

  DOI：

  10.1002/chir.23412

文献信息

• Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans
  作者：Ping Sun、Chunlei Wang、Zachary S. Breitbach、Ying Zhang、Daniel W. Armstrong

  DOI：10.1021/ac902257a

  日期：2009.12.15

  An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic- and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromatic-functionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high “loadability” and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.

  首次引入一类不寻常的手性选择剂——环糊精作为键合型手性固定相。与天然环糊精（CFs）相比，其作为手性选择剂的能力相当有限，而脂族和芳族功能化的CF6具有独特且截然不同的对映体选择性。事实上，它们能够分离非常广泛的消旋化合物。特别是，低取代度的脂族衍生化CF6能够基线分离所有测试的手性伯胺。似乎部分衍生化作用于CF6分子会破坏分子内部的氢键，从而使分子核心更易接近。相比之下，高度芳族功能化的CF6固定相在伯胺的对映选择能力方面丧失了大部分能力，但它们对大多数其他类型的分析物获得了广泛的选择性。这类固定相还表现出高“负荷能力”，因此具有在制备分离方面的巨大潜力。对映体选择性的变化通常可以与选择剂的独特结构特征相关联。分离主要在有机溶剂存在下发生。
• TERMITICIDE COMPOSITION AND METHODS FOR TREATING TERMITES
  申请人：ADAMA MAKHTESHIM LTD.

  公开号：US20160029637A1

  公开（公告）日：2016-02-04

  A termiticide concentrate comprising a termiticide composition comprising a phenylpyrazole, such as fipronil and a neonicotinoid, such as imidacloprid, wherein the composition is dispersed in an aqueous medium to form the termiticide concentrate. The concentrate containing the combination of active termiticides provides an increased efficacy not exhibited by either active when used alone.

  一种白蚁杀虫剂浓缩液，包括一种含有苯基吡唑类化合物的白蚁杀虫剂组合物，例如氟虫腈和一种含有新烟碱类化合物的组合物，例如吡虫啉，其中该组合物分散在水性介质中以形成白蚁杀虫剂浓缩液。该浓缩液含有活性白蚁杀虫剂的组合，比单独使用任一活性剂表现出更高的功效。
• Spot-on pesticide composition
  申请人：Sergeant's Pet Care Products, Inc.

  公开号：EP2803265A1

  公开（公告）日：2014-11-19

  A spot-on pesticide composition for animals, specifically mammals, including dogs and cats, which composition comprises a combination of active components, including fipronil and a pyrethroid, and optionally an insect growth regulator, in doses and proportions which are parasiticidally effective against a variety of insects and pests, and in a formulation which is convenient for local application to the animal's skin, preferably localized over a small surface area.

  一种用于动物，特别是哺乳动物（包括狗和猫）的点涂杀虫剂组合物，该组合物由活性成分（包括氟虫腈、拟除虫菊酯和昆虫生长调节剂）组合而成，其剂量和比例对多种昆虫和害虫具有寄生效果，其配方便于在动物皮肤上局部施用，最好是局部小面积施用。
• Proteins toxic to Hemipteran insect species
  申请人：Monsanto Technology LLC

  公开号：US10188115B2

  公开（公告）日：2019-01-29

  The present invention discloses Hemipteran insect inhibitory proteins, methods of using such proteins, nucleotide sequences encoding such proteins, methods of detecting and isolating such proteins, and their use in agricultural systems.

  本发明公开了半翅目昆虫抑制蛋白、使用这种蛋白的方法、编码这种蛋白的核苷酸序列、检测和分离这种蛋白的方法以及它们在农业系统中的用途。
• Compositions and methods for deploying a transgenic refuge as a seed blend
  申请人：Monsanto Technology LLC

  公开号：US10745713B2

  公开（公告）日：2020-08-18

  Methods and compositions for deploying refuge seeds together with transgenic crop seeds are provided. The refuge seeds can be non-transgenic seeds of a similar variety to that of the transgenic crop seeds, or the refuge seeds can be a transgenic variety, but in either case lacking a transgenic trait conferring pest protection found in the transgenic crop seeds.

  本文提供了将避难种子与转基因作物种子一起播种的方法和组合物。保护种子可以是与转基因作物种子品种相似的非转基因种子，或者保护种子可以是转基因品种，但无论哪种情况，都缺乏转基因作物种子中具有害虫保护功能的转基因性状。