吲哚卡威 | 144171-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 吲哚卡威
• 英文名称: DPX-JT333
• 英文别名: indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid, 7-chloro-2,5-dihydro-2-[[[4-(trifluoromethoxy)phenyl]amino]carbonyl]-, methyl ester；methyl-7-chloro-2,5-dihydro-2-[[[(4-trifluoromethoxy)phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H) carboxylate；Indoxacarb Impurity 5；methyl 7-chloro-2-[[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
• CAS: 144171-39-1
• 化学式: C₂₀H₁₅ClF₃N₃O₅
• 分子量: 469.804
• InChiKey: ZQBDNGWVXFMUHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  吲哚卡威 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 7-chloro-4a-(hydroxymethyl)-N-(4-(trifluoromethoxy)phenyl)-4a,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-2(3H)-carboxamide
  参考文献：
  名称：

  基于茚虫威作为潜在的钠通道阻滞剂/调节剂的新型三环恶二嗪4a-甲基酯的发现

  摘要：

  茚虫威，一种商业化的恶二嗪类杀虫剂，几乎不可逆地阻止了开放/灭活，但没有静息的钠通道。构效关系表明，恶二嗪环中手性原子位置的取代基对恶二嗪杀虫剂的生物活性非常重要。在这里，我们合成了一系列的三环恶二嗪4a-甲酯衍生物。恶二嗪环中的手性原子已被差向异构化并被除草酸或肉桂酸衍生物取代。三环部分中的苯环被氯，氟或溴原子取代，而氮连接的苯环被三氟甲基或三氟甲氧基取代。这些化合物对斜纹夜蛾的毒性F.被评估。通过快速柱色谱分离大多数毒性化合物J7和J9的非对映异构体，并带有除草酸部分。极性更大的非对映异构体J7-L-Rf和J9-L-Rf以及具有肉桂酸部分的化合物J24和J26表现出最高的杀虫活性。我们进一步使用蒙特卡洛能量最小化技术将化合物J7和J24停靠在开放蟑螂钠通道的基于NavMs的同源性模型中。在低能结合模式下，该化合物与内部孔和结构域界面中的残基相互作用，这些残基先前被认为有助于拟除虫菊酯和

  DOI：

  10.1021/acs.jafc.9b00826
• 作为产物：
  描述：

  5-氯-1-氧代-2,3-二氢-1H-茚-2-羧酸甲酯 在 叔丁基过氧化氢 、 四磷十氧化物 、 一水合肼 、 溶剂黄146 、 辛可宁 作用下， 以 四氢呋喃 、 甲醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.5h， 生成 吲哚卡威
  参考文献：
  名称：

  噁二嗪衍生物及其制备方法和应用

  摘要：

  本发明公开了一种噁二嗪衍生物及其制备方法和应用。所述的噁二嗪衍生物分子结构如式(Ⅰ)所示。本发明提供所述噁二嗪衍生物的制备方法和在制备防治农业或卫生害虫的农药或用于制备防治动物寄生虫的药物制剂方面的应用。本发明的噁二嗪衍生物因含有对昆虫钠离子通道两种不同作用方式的药效团，可达到协同增效的目的，对害虫表现出更高的生物活性，且可达到增加防治谱的目的，应用前景广阔。

  公开号：

  CN107474021B

文献信息

• Catalytic system for scalable preparation of indoxacarb
  申请人：Adama Makhteshim Ltd.

  公开号：US10961206B2

  公开（公告）日：2021-03-30

  It is an object of the present invention to provide a novel and advantageous process for commercially preparing of indoxacarb which is racemic or enantiomerically enriched at chiral center from its amide precursor using a new catalytic system. More particularly, it relates to an efficient method of preparation of indoxacarb which is racemic or enantiomerically enriched at chiral center from methyl-7-chloro-2,5-dihydro-2-[[[(4-tritluoromethoxy)phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H) carboxylate represented as formula (I) using methoxycarbonylation agent and metal salt of methylsulfinylmethylide in hydrocarbon solvent in the presence of organic base and phase transfer catalyst.

  本发明的目的是提供一种新颖而有利的工艺，利用一种新的催化体系，从其酰胺前体中商业化制备外消旋的或手性中心对映体富集的茚草克。 更具体地说，它涉及一种从甲基-7-氯-2,5-二氢-2-[[[(4-三氟甲氧基)苯基]氨基]羰基]-茚并[1、2-e][1,3,4]恶二嗪-4a(3H)羧酸甲酯的手性中心富集。
• Design, synthesis and structure–activity relationship of indoxacarb analogs as voltage-gated sodium channel blocker
  作者：Wenbo Hao、Chunling Fu、Huijuan Yu、Jian Chen、Hanhong Xu、Guang Shao、Dingxin Jiang

  DOI：10.1016/j.bmcl.2015.08.058

  日期：2015.10

  Indoxacarb, the first commercialized pyrazoline-type sodium-channel blocker, is a commonly used insecticide because of high selectivity. To discover sodium-channel blocker with high insecticidal activity, a series of novel indoxacarb analogs were designed and synthesized by judicious structural modifications of the substituent group of C-5, C-6 in indenone and C-4' in benzene ring. Some analogs exhibited significant insecticidal activities against Spodoptera litura F. and excellent BgNav1-1a channel inhibitory activity. The structure-activity analysis indicated that the presence of strong electron-withdrawing group and decreased steric hindrance of indenone ring (R-1, R-2) in 5- and 6-position could enhance larvicidal activity and BgNav1-1a channel inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.
• The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides
  作者：Stephen F McCann、Gary D Annis、Rafael Shapiro、David W Piotrowski、George P Lahm、Jeffery K Long、Kevin C Lee、Margaret M Hughes、Brian J Myers、Sandra M Griswold、Bonita M Reeves、Robert W March、Paula L Sharpe、Patrick Lowder、William E Barnette、Keith D Wing

  DOI：10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o

  日期：2001.2

  The evolution of the insecticidal pyrazoline moiety that was originally discovered in 1972 has led to the discovery of a new crop insecticide, indoxacarb, which is the first commercialized pyrazoline-type sodium-channel blocker. Both monocyclic and fused-tricyclic pyrazolines and pyridazines, as well as structurally related semicarbazones were examined prior to the discovery of analogous tricyclic oxadiazines which had similarly high activity as well as favorable environmental dissipation rates and low toxicity to non-target organisms. The eventual leading candidate, DPX-JW062, was originally obtained as a racemic molecule, but a chiral synthesis was developed which produces material that is 50% ee in the insecticidal (+)-S-enantiomer (DPX-MP062, indoxacarb). (C) 2001 Society of Chemical Industry.
• ARTHROPODICIDAL CARBOXANILIDES
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：EP0565574B1

  公开（公告）日：1995-08-02
• CATALYTIC SYSTEM FOR SCALABLE PREPARATION OF INDOXACARB
  申请人：Adama Makhteshim Ltd.

  公开号：EP3601243B1

  公开（公告）日：2021-11-10