N'-(tert-butyl)-3-methylbenzohydrazide | 115216-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(tert-butyl)-3-methylbenzohydrazide
• 英文别名: N'-tert-butyl-3-methylbenzohydrazide
• CAS: 115216-07-4
• 化学式: C₁₂H₁₈N₂O
• 分子量: 206.288
• InChiKey: NNXBTZKENSEFOG-UHFFFAOYSA-N

物化性质

• 沸点：
  289.5±23.0 °C(predicted)
• 密度：
  1.009±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-methyl-1,2,3-thiadiazole-4-carbonyl chloride 、 N'-(tert-butyl)-3-methylbenzohydrazide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以51%的产率得到
  参考文献：
  名称：

  Synthesis and bioactivity of N-tert-butyl-N′-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides

  摘要：

  A series of novel N-tert-butyl-N'-acyl-5-methyl-1,2,3-thiadiazole-4-carbohyclrazides were designed and synthesized. Their structures were characterized by melting points, H-1 NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in viva at 50 mu g/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development. (C) 2012 Zhi Jin Fan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.09.024
• 作为产物：
  描述：

  间甲基苯甲酸 在 氯化亚砜 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 N'-(tert-butyl)-3-methylbenzohydrazide
  参考文献：
  名称：

  Synthesis and bioactivity of N-tert-butyl-N′-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides

  摘要：

  A series of novel N-tert-butyl-N'-acyl-5-methyl-1,2,3-thiadiazole-4-carbohyclrazides were designed and synthesized. Their structures were characterized by melting points, H-1 NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in viva at 50 mu g/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development. (C) 2012 Zhi Jin Fan. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2012.09.024

文献信息

• Synthesis and Bioactivities Evaluation of Novel Anthranilic Diamides Containing <i>N</i> ‐( <i>tert</i> ‐Butyl)benzohydrazide Moiety as Potent Ryanodine Receptor Activator
  作者：Yunyun Zhou、Wei Wei、Liangliang Zhu、Yuxin Li

  DOI：10.1002/cjoc.201900073

  日期：2019.6

  Anthranilic diamides have been proven to be a class of efficacious and safe insecticides targeting ryanodine receptors (RyRs) during the last decade. In order to develop innovative scaffolds with high insecticidal activity, two series of N‐pyridylpyrazole derivatives containing N‐(tert‐butyl)benzohydrazide substructures were designed and synthesized. Their insecticidal activities against oriental armyworm

  在过去的十年中，邻氨基苯甲酰胺已被证明是针对瑞丹素受体（RyRs）的一类有效且安全的杀虫剂。为了开发具有高杀虫活性的创新支架，设计并合成了两个包含N-（叔丁基）苯并肼亚结构的N-吡啶基吡唑衍生物系列。它们对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）具有杀虫活性。）进行了评估。初步的生物测定结果表明，某些新化合物对东方粘虫和小菜蛾具有良好的杀虫活性。这些化合物的作用方式已通过钙显像技术进行了验证，结果表明，一些新化合物可以有效调节昆虫胞浆中的Ca 2+水平，并破坏细胞内钙稳态，表明其中某些化合物是该化合物的有效激活剂。 RyRs。
• Five-membered heterocyclic derivatives of N'-substituted-N,N'-Diacylhydrazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0261755A2

  公开（公告）日：1988-03-30

  Certain five-membered heterocyclic derivatives of N'- substi uted-N,N'-diacylhydrazines are insecticidally active comp sunds and may be used, optionally in compositions cont1 ning agronomically acceptable diluent or carrier, to con at insects, particularly those from the order Lepi- dop t ra.

  某些 N'-亚基-N,N'-二酰肼的五元杂环衍生物是具有杀虫活性的化合物，可用于杀灭昆虫，特别是鳞翅目昆虫，也可用于含有农艺上可接受的稀释剂或载体的组合物中。
• Insecticidal ferrocenoyl acylhydrazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0480661A1

  公开（公告）日：1992-04-15

  Insecticicidal compounds of the formula wherein one of A or B is ferrocenyl and the other of A or B is phenyl or substituted phenyl and R is branched alkyl are effective in controlling the Southern Armyworm and Mexican Bean Beetle.

  式中的杀虫化合物 其中 A 或 B 之一为二茂铁基，A 或 B 之二为苯基或取代苯基，R 为支链烷基的杀虫化合物可有效防治南方军团虫和墨西哥豆甲虫。
• Six-membered heterocyclic derivatives of N'substituted-N,N'-diacylhydrazines
  申请人：ROHM AND HAAS COMPANY

  公开号：EP0253468B1

  公开（公告）日：1991-11-06
• Synthesis and Insecticidal Activity of <i>N</i>-<i>tert</i>-Butyl-<i>N</i>,<i>N</i>′-diacylhydrazines Containing 1,2,3-Thiadiazoles
  作者：Huan Wang、Zhikun Yang、Zhijin Fan、Qingjun Wu、Youjun Zhang、Na Mi、Shouxin Wang、Zhengcai Zhang、Haibin Song、Feng Liu

  DOI：10.1021/jf104004q

  日期：2011.1.26

  N-tert-Butyl-N,N'-diacylhydrazines are nonsteroidal ecdysone agonists used as environmental benign pest regulators. In this paper, two series of new N-tert-butyl-N,N'-diacylhydrazine derivatives containing 1,2,3-thiadiazole were designed and synthesized. All structures of the synthesized compounds were confirmed by proton nuclear magnetic resonance (H-1 NMR), infrared spectroscopy (IR), and high-resolution mass spectrometry (HRMS). Bioasssay results indicated that most of the synthesized compounds possessed good insecticidal activities against Plutella xylostella L. and Culex pipiens pallens as compared with the positive control, tebufenozide. The results of this study indicated that 1,2,3-thiadiazoles, as an important active substructure, could improve or maintain the activity of the dicylhydrazines and favor novel pesticide development.