N-tert-butyl-N'-(3-methoxybenzoyl)-4-methylthiadiazole-5-carbohydrazide | 1202365-86-3

• 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-N'-(3-methoxybenzoyl)-4-methylthiadiazole-5-carbohydrazide
• CAS: 1202365-86-3
• 化学式: C₁₆H₂₀N₄O₃S
• 分子量: 348.426
• InChiKey: IBIYWALKDABCKS-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间甲氧基苯甲酰氯 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 N-tert-butyl-N'-(3-methoxybenzoyl)-4-methylthiadiazole-5-carbohydrazide
  参考文献：
  名称：

  Synthesis and Insecticidal Activity of N-tert-Butyl-N,N′-diacylhydrazines Containing 1,2,3-Thiadiazoles

  摘要：

  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.

  DOI：

  10.1021/jf104004q

文献信息

• Synthesis, Crystal Structure and Biological Activity of N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine
  作者：Jie Huang、Huan Wang、Zhi-Jin Fan、Hai-Bin Song、Hui Zhao、Yun Huang、Polina E. Prokhorova、Nataliya P. Belskaya、Yury Yu. Morzherin、Vasiliy A. Bakulev

  DOI：10.1007/s10870-011-0189-1

  日期：2011.12

  The title compound, N′-tert-butyl-N-(3-methoxylbenzoyl)-N-(4-methyl-1,2,3-thiadiazole-5-formylhydrazine (C16H20N4O3S) was prepared from the reaction of 4-methyl-1,2,3-thiadiazole-5-carbonyl chloride with N′-tert-Butyl-3-methoxylbenzohydrazine, and its structure was characterized by 1Hydrogen Nuclear Magnetic Resonance, High-Resolution Mass Spectrometry, IR spectra, and single crystal X-ray diffraction. The crystal of the title compound belongs to monoclinic system, space group P 21/c with cell parameters a = 17.986(2) Å, b = 8.0180(10) Å, c = 12.0190(14) Å, α = 90°, β = 91.160(5)°, γ = 90°, V = 1732.9(4) Å3, Z = 4, D c  = 1.335 g/cm3, μ (Mo Ka) = 0.209 mm−1, F (000) = 736, R = 0.0367 and wR = 0.0932. X-ray diffraction analysis indicates that all rings in the title compound are non-planar. The bioassay results indicated that, the title compound had good fungicide activity against Sclerotinia sclerotiorum, certain extent of insecticidal activity against Plutella xylostella L.   .

  标题化合物N′-叔丁基-N-(3-甲氧基苯甲酰基)-N-(4-甲基-1,2,3-噻二唑-5-甲酰肼)(C16H20N4O3S)是由4-甲基-1,2,3-噻二唑-5-甲酰氯与N′-叔丁基-3-甲氧基苯甲酰肼反应制备的，其结构通过氢核磁共振、高分辨质谱、红外光谱和单晶X射线衍射鉴定。标题化合物的晶体属于单斜晶系，空间群P 21/c，晶胞参数a = 17.986(2) Å，b = 8.0180(10) Å，c = 12.0190(14) Å，α = 90°，β = 91.160(5)°，γ = 90°，V = 1732.9(4) Å3，Z = 4，D c = 1.335 g/cm3，μ (Mo Ka) = 0.209 mm−1，F (000) = 736，R = 0.0367，wR = 0.0932。X射线衍射分析表明，标题化合物中的所有环都是非平面的。生物活性测试结果表明，标题化合物对核盘菌(Sclerotinia sclerotiorum)具有良好的杀菌活性，对小菜蛾(Plutella xylostella L.)具有一定程度的杀虫活性。
• 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.