2-amino-5-bromo-N-cyclopropyl-3-methylbenzamide | 1006619-91-5

• 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: 2-amino-5-bromo-N-cyclopropyl-3-methylbenzamide
• CAS: 1006619-91-5
• 化学式: C₁₁H₁₃BrN₂O
• 分子量: 269.141
• InChiKey: LBTDPUBCMHCNCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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-amino-5-bromo-N-cyclopropyl-3-methylbenzamide 、 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-(3-chloropyridin-2-yl)-5-prop-2-ynyloxy-2H-pyrazole-3-carboxylic acid (4-bromo-2-cyclopropylcarbamoyl-6-methylphenyl)amide
  参考文献：
  名称：

  新型含炔丙基醚基邻氨基苯甲酰胺杀虫剂的合成，晶体结构和生物活性

  摘要：

  为了寻找高活性，低毒，低残留的环境友好的杀虫剂，设计并合成了一系列新型的含炔丙基醚的邻氨基苯甲酰胺。所有化合物均通过1 H NMR光谱，高分辨率质谱或元素分析进行表征。通过X射线衍射确定18g的单晶结构。评价了新化合物对鳞翅目害虫的杀虫活性。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。

  DOI：

  10.1002/jhet.2434
• 作为产物：
  描述：

  2-氨基-5-氯-3-甲基苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-amino-5-bromo-N-cyclopropyl-3-methylbenzamide
  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

文献信息

• Synthesis, crystal structure and biological activity of a novel anthranilic diamide insecticide containing allyl ether
  作者：Yu Zhao、Li-xia Xiong、Li-ping Xu、Hongxue Wang、Han Xu、Hua-bin Li、Jun Tong、Zheng-ming Li

  DOI：10.1007/s11164-012-0820-6

  日期：2013.9

  search of environmentally benign insecticides with high activity, low toxicity and low residue, a series of novel anthranilic diamides containing allyl ether were designed and synthesized. All the compounds were characterized by 1H NMR spectroscopy, HRMS or elemental analysis. The single crystal structure of 18e was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated

  为了寻找高活性，低毒性和低残留的环境友好的杀虫剂，设计并合成了一系列新型的含烯丙基醚的邻氨基苯甲酰胺。所有化合物均通过1 H NMR光谱，HRMS或元素分析进行表征。通过X射线衍射确定18e的单晶结构。评价了新化合物的杀虫活性。结果表明，某些化合物对鳞翅目害虫表现出优异的杀虫活性。在该系列化合物中，18l在测试浓度下对Mythimna独立的Walker和Plutella xylostella Linnaeus表现出100％的杀幼虫活性。
• 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 Evaluation of Novel Anthranilic Diamides Derivatives Containing <scp>4‐Chlorine</scp> Substituted <scp> <i>N</i> ‐Pyridylpyrazole </scp>
  作者：Huangong Li、Yangyang Zhao、Pengwei Sun、Li Gao、Yuxin Li、Lixia Xiong、Na Yang、Sha Zhou、Zhengming Li

  DOI：10.1002/cjoc.202000013

  日期：2021.1

  To search for potent insecticides targeting at ryanodine receptors (RyRs), a series of novel anthranilic diamides analogs containing 4‐chlorine N‐pyridylpyrazole were designed and synthesized. Their insecticidal activities were evaluated and the preliminary structure‐activity relationships (SARs) were discussed. The insecticidal results showed that some of the compounds (8a—8h, 8m, 8n) exhibited good

  为了寻找针对ryanodine受体（RyRs）的有效杀虫剂，设计并合成了一系列新型的含有4-氯N-吡啶基吡唑的邻氨基苯甲酰胺类类似物。对它们的杀虫活性进行了评估，并讨论了其初步的构效关系。杀虫结果表明，某些化合物（8a-8h，8m，8n）在2.5 mg·L –1时对东方粘虫表现出良好的杀幼虫活性，而化合物8m在0.5 mg·L –1时具有60％的杀虫活性。对于小菜蛾而言，8m的活性比氯吡喹更好，为一百倍。钙成像技术实验结果表明，化合物8m可以增加细胞内[Ca 2+]我。通过神经元预温育实验，结果证实了该系列化合物的靶标可能是东方粘虫中央幼虫神经元中的RyRs。结果表明，化合物8m可能作为昆虫雷诺碱受体的潜在调节剂。
• Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study
  作者：Guantian Yang、Cong Zhou、Yutong Wang、Yuxin Li、Yucheng Gu、Zhong Li、Jiagao Cheng、Xiaoyong Xu

  DOI：10.1021/acs.jafc.2c07680

  日期：2023.2.15

  In order to develop anthranilic diamides with novel chemotypes, a series of anthranilic diamides with acrylamide linkers were designed and synthesized. The results of preliminary bioassays indicated that compounds with a monofluoroalkene amide linker (Z-isomer) exhibited good larvicidal activity against lepidopteran pests. The LC50 values of compound A23 against Mythimna separata and Plutella xylostella

  为了开发具有新化学型的邻氨基苯甲酸二酰胺，设计并合成了一系列具有丙烯酰胺连接体的邻氨基苯甲酸二酰胺。初步生物测定结果表明，具有单氟烯烃酰胺接头（Z-异构体）的化合物对鳞翅目害虫表现出良好的杀幼虫活性。化合物A23对Mythimna separata和Plutella xylostella的LC 50值分别为1.44和3.48 mg·L –1，而对氯虫苯甲酰胺的LC 50 值分别为0.08和0.06 mg·L –1。化合物A23对耐药菌株和易感菌株也表现出相同水平的致死效力草地贪夜蛾50 mg·L –1。化合物A23在试验幼虫中表现出与氯虫苯甲酰胺相似的症状。进行比较分子场分析以证明构效关系。中枢神经元钙成像实验表明，单氟烯烃化合物是潜在的兰尼碱受体 (RyR) 激活剂，可激活内质网和细胞膜中的钙通道。分子对接表明A23与小菜蛾RyR的结合能力优于氯虫苯甲酰胺。A23与小菜蛾RyR的MM|GBSA