2-氨基-N-叔丁基-5-氯-3-甲基苯甲酰胺 | 1006619-88-0

• 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: 2-氨基-N-叔丁基-5-氯-3-甲基苯甲酰胺
• 英文名称: 2-amino-N-(tert-butyl)-5-chloro-3-methylbenzamide
• 英文别名: 2-amino-N-tert-butyl-5-chloro-3-methylbenzamide
• CAS: 1006619-88-0
• 化学式: C₁₂H₁₇ClN₂O
• 分子量: 240.733
• InChiKey: CJVALTAYSVZEPE-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  340.1±42.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-N-叔丁基-5-氯-3-甲基苯甲酰胺 、 以 乙腈 为溶剂， 生成 N-[[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]carbamothioyl]-2-(3-chloropyridin-2-yl)-5-(2,2,2-trifluoroethoxy)pyrazole-3-carboxamide
  参考文献：
  名称：

  Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides

  摘要：

  Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, H-1 NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.

  DOI：

  10.1021/jf4012467
• 作为产物：
  描述：

  N1-(4-氯-2-甲基苯基)-2-氯乙酰胺 在 吡啶 、 硫酸 、 盐酸羟胺 、 双氧水 、 copper(II) acetate monohydrate 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 水 、 1,2-二氯乙烷 、 异丙醇 、 乙腈 为溶剂， 反应 90.25h， 生成 2-氨基-N-叔丁基-5-氯-3-甲基苯甲酰胺
  参考文献：
  名称：

  [EN] A PROCESS FOR THE SYNTHESIS OF ANTHRANILIC ACID/AMIDE COMPOUNDS AND INTERMEDIATES THEREOF
  [FR] PROCÉDÉ DE SYNTHÈSE DE COMPOSÉS ACIDE ANTHRANILIQUE/AMIDE ET INTERMÉDIAIRES DE CEUX-CI

  摘要：

  本发明公开了一种合成化合物的方法，该化合物的化学式为(VII)或其盐，其中，R、R1、R2、R3、R4a和R4b如详细描述中所定义。该方法还包括合成化学式(I)的苯甲酰二胺化合物。

  公开号：

  WO2022064454A1

文献信息

• Synthesis of Novel 3-Chloropyridin-2-yl-Pyrazole Derivatives and their Insecticidal, Fungicidal Activities and QSAR Study
  作者：Ji-Feng Zhang、Chen Liu、Yi Ma、Bao-Lei Wang、Li-Xia Xiong、Shu-Jing Yu、Zheng-Ming Li

  DOI：10.2174/1570180811310060005

  日期：2013.5.1

  In our early study, a series of anthranilic diamides containing acylthiourea linker (C) was reported to display favorable activities. Based on that research, four series of novel pyridylpyrazole derivatives (D-G) derived from C were designed and synthesized. Totally 24 compounds were synthesized and all the compounds were characterized by melting points, 1H NMR, 13C NMR and HRMS. Bioassay results indicated that compounds 5b, 5c and 6b showed 100 % insecticidal activities against oriental armyworm (Mythimna separata) at 200mg/L. Their fungicidal activities against A. solani, F. graminearum, P. capsici, S. sclerotiorum, B. cinerea and R. solani were evaluated and the results indicated that compounds 7a-g which contained acylguanidine linker showed favourable antibacterial activity against B. cinerea, among which 7d and 7f showed 97.5 % inhibitory activities against B. cinerea at 50mg/L. To further explore the comprehensive structure-activity relationship on the basis of insecticidal activity data, comparative molecular field analysis (CoMFA) was performed, and a statistically reliable model with good predictive power (r2 = 0.972, q2 = 0.604) was achieved.

  在我们早期的研究中，报道了一系列含有酰基硫脲连接基（C）的邻氨基苯甲酰胺显示了良好的活性。基于这一研究，设计并合成了从C衍生出的四个系列新型吡啶基吡唑衍生物（D-G）。共合成24个化合物，所有化合物均通过熔点、1H NMR、13C NMR和HRMS进行了表征。生物测定结果表明，化合物5b、5c和6b对东方粘虫（Mythimna separata）在200mg/L下显示出100%的杀虫活性。评估了它们对A. solani、F. graminearum、P. capsici、S. sclerotiorum、B. cinerea和R. solani的杀菌活性，结果显示含有酰基胍连接基的化合物7a-g对B. cinerea显示出良好的抗菌活性，其中7d和7f在50mg/L下对B. cinerea显示出97.5%的抑制活性。为进一步探究基于杀虫活性数据的全面构效关系，进行了比较分子场分析（CoMFA），并获得了统计上可靠且预测能力良好的模型（r2 = 0.972，q2 = 0.604）。
• Synthesis and insecticidal activities of 2,3-dihydroquinazolin-4(1H)-one derivatives targeting calcium channel
  作者：Yunyun Zhou、Qi Feng、Fengjuan Di、Qiaoxiao Liu、Duoyi Wang、Youwei Chen、Lixia Xiong、Haibin Song、Yuxin Li、Zhengming Li

  DOI：10.1016/j.bmc.2013.06.060

  日期：2013.9

  A series of compounds containing dihydroquinazolinone moiety was designed and synthesized. Amine bridge part was changed in comparison with known anthranilic diamides insecticides. Their insecticidal activities against oriental armyworm (Mythimna separata) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compounds 5a and 5k showed

  设计并合成了一系列含有二氢喹唑啉酮部分的化合物。与已知的邻氨基苯甲酰胺类杀虫剂相比，胺桥部分发生了变化。它们对东方粘虫（Mythimna separata）的杀虫活性表明，在所测试的浓度下，大多数化合物显示出中等至高活性。特别是，化合物5a和5k在5 mg / L的浓度下对东方粘虫表现出80％的杀幼虫活性。本研究还探讨了目标化合物可能对自斜纹夜蛾第三龄幼虫分离的中枢神经元的高压门控钙通道和内质网中钙通道的影响使用全细胞膜片钳和钙成像技术。结果表明，化合物5a弱地激活了S. exigua的中枢神经元中的高压门控钙通道。的峰值电流仅在与0.22μM处理后的10分钟的记录结束增加初始值的6％5a中，氯虫苯甲酰胺，同时具有相反的效果。很好地研究了5a对神经元细胞内钙离子浓度（[Ca 2+ ] i）的影响。实验结果表明，这些新化合物与氯虫腈相比具有不同的作用机理。
• Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Acylthiourea and Acylurea
  作者：Ji-Feng Zhang、Jun-Ying Xu、Bao-Lei Wang、Yu-Xin Li、Li-Xia Xiong、Yong-Qiang Li、Yi Ma、Zheng-Ming Li

  DOI：10.1021/jf302446c

  日期：2012.8.8

  xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a–13e, 14a–14e, and 15a–15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a–17k) exhibited

  设计并合成了两个系列的含酰基硫脲和酰基脲接头的邻氨基苯甲酰胺，其接头的长度和柔性有所变化，可与已知的邻氨基二酰胺杀虫剂进行比较。总共合成了26种新化合物，所有化合物均通过1 H核磁共振和高分辨率质谱进行了表征。评估了它们对东方粘虫（Mythimna separata），蚊虫幼虫（Culex pipiens pallens）和小菜蛾（Plutella xylostella）的杀虫活性。对东方粘虫的杀幼虫活性表明，在某些结构中引入酰基硫脲可以保留其杀虫活性。15种化合物中的8种（13a – 13e，14a – 14e和15a – 15e）在10 mg / L时表现出100％的杀幼虫活性。然而，酰脲的引入降低了杀虫活性；11种化合物（17a – 17k）中只有3种在200 mg / L时表现出100％的杀幼虫活性。全细胞膜片钳技术表明，化合物13b和绿蒽醌对电压门控钙通道表现出相似的作用。钙成像
• Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Modified <i>N</i>-Pyridylpyrazoles
  作者：Qi Feng、Zhi-Li Liu、Li-Xia Xiong、Ming-Zhong Wang、Yong-Qiang Li、Zheng-Ming Li

  DOI：10.1021/jf102842r

  日期：2010.12.8

  In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by 1H NMR, 13C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. Their insecticidal activities against oriental armyworm (Mythimna

  为了寻找针对ryanodine受体的新型杀虫剂，设计并合成了四个新系列的含有修饰的N-吡啶基吡唑类的邻氨基苯甲酰胺。通过1 H NMR，13 C NMR和HRMS对所有化合物进行表征和确认。通过X射线衍射确定10c的单晶结构。它们对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）的杀虫活性表明，大多数化合物在测试浓度下均表现出中等至高活性，而化合物19在0.125 mg / L的浓度下显示出相当高的活性。初步的构效关系（SAR）进行了讨论。
• Synthesis and insecticidal evaluation of novel anthranilic diamides containing N-substitued nitrophenylpyrazole
  作者：Xiulan Zhang、Yuxin Li、Jinlong Ma、Hongwei Zhu、Baolei Wang、Mingzhen Mao、Lixia Xiong、Yongqiang Li、Zhengming Li

  DOI：10.1016/j.bmc.2013.11.038

  日期：2014.1

  associated with conventional insecticides and to search for potent insecticides targeting at ryanodine receptor (RyR), a series of novel anthranilic diamides containing N-substitued nitrophenylpyrazole were designed and synthesized. The insecticidal activities of target compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) were evaluated in our greenhouse by bio-assay

  为了应对发展中的害虫抗性和与常规杀虫剂相关的生态问题，并寻找针对瑞丹定受体（RyR）的有效杀虫剂，设计并合成了一系列新型的含有N取代的硝基苯基吡唑的邻氨基苯甲酰胺。通过生物测定试验评价了目标化合物对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）的杀虫活性，并简要讨论了其相对的构效关系。大多数化合物均表现出中等至高活性，其中G 7和K 5对东方粘虫和K 2具有高活性。和K 4对抗小菜蛾的效果甚至优于对照氯虫腈。钙成像技术用于研究几种典型标题化合物对[Ca 2+ ] i的影响，尤其是G 7对神经元细胞内钙离子浓度（[Ca 2+ ] i）的影响，这表明：一些标题化合物是RyR的有效激活剂。