2-氨基-5-氯-N-异丙基-3-甲基苯甲酰胺 | 1006619-87-9

• 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-5-氯-N-异丙基-3-甲基苯甲酰胺
• 英文名称: 2-amino-5-chloro-N-isopropyl-3-methylbenzamide
• 英文别名: 2-amino-3-methyl-5-chloro-N-isopropylbenzamide；2-amino-5-chloro-3-methyl-N-propan-2-ylbenzamide
• CAS: 1006619-87-9
• 化学式: C₁₁H₁₅ClN₂O
• 分子量: 226.706
• InChiKey: DNMREPJYFNXQPO-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C
• 沸点：
  331.3±42.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• 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-氨基-5-氯-N-异丙基-3-甲基苯甲酰胺 、 以 乙腈 为溶剂， 生成 N-[[4-chloro-2-methyl-6-(propan-2-ylcarbamoyl)phenyl]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：

  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， 生成 2-氨基-5-氯-N-异丙基-3-甲基苯甲酰胺
  参考文献：
  名称：

  新型含改性N-吡啶基吡唑类邻氨基苯甲酰胺的合成及杀虫活性

  摘要：

  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。

  DOI：

  10.1021/jf102842r

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, Insecticidal Activities, and Structure–Activity Relationship of Phenylpyrazole Derivatives Containing a Fluoro-Substituted Benzene Moiety
  作者：Yangyang Zhao、Li Gao、Huangong Li、Pengwei Sun、Fanfei Meng、Yan Zhang、Yongtao Xie、Binqiao Sun、Sha Zhou、Yi Ma、Lixia Xiong、Na Yang、Yuxin Li、Zhengming Li

  DOI：10.1021/acs.jafc.9b08090

  日期：2020.10.7

  Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted

  氟化有机化合物代表了一个日益重要的商业化学品家族。将氟引入活性成分已成为开发现代农作物保护产品的有效途径。考虑到氟的特殊性质以及二酰胺类杀虫剂的高效性和选择性，我们设计并合成了27种含有氟代苯基吡唑的邻氨基苯甲酰胺类类似物。初步的生物测定表明，大多数目标化合物对分离的Mythimna separata和Plutella xylostella具有良好的生物学活性。含有2,4,6-三氟取代苯环的化合物IIIf在0.1 mg L –1时显示出对分离支原体的杀虫活性为43％，而对照中的氯蒽醌含量为36％。IIIe在10 –5 mg L –1时对小菜蛾的活性为94％，而对照为70％。因此，将氟引入二酰胺杀虫剂中对于增加活性是有用的。昆虫电生理研究表明，IIIf可以提高分离的第三个分离支原体幼虫神经细胞中的钙浓度，这进一步证实了赖多碱受体（RyR）是其潜在的靶标。
• Synthesis of novel N-pyridylpyrazole derivatives containing 1,2,4-oxadiazole moiety via 1,3-dipolar cycloaddition and their structures and biological activities
  作者：Yan Zhang、Junfeng Shang、Huan Li、Hang Liu、Haibin Song、Baolei Wang、Zhengming Li

  DOI：10.1016/j.cclet.2019.10.039

  日期：2020.5

  characteristics, and the relevance of the structure and the reaction activity of this type of compounds. The preliminary bioassays indicated that several compounds had good insecticidal activities, among which 12c showed a lethality rate of 80% towards Mythimna separata Walker at 200 μg/mL; some of the compounds exhibited favorable fungicidal activities at 50 μg/mL against Physalospora piricola, Rhizoctonia cereal

  摘要以1,3-偶极环加成反应为原料，以戊醛，吡啶基吡唑羧酸和芳基胺为原料，高效合成了一系列新型的含1,2,4-恶二唑的N-吡啶基吡唑衍生物12a-h。通过熔点，1 H NMR，13 C NMR和元素分析或HRMS鉴定其结构。对12c和12g单晶结构的探索揭示了立体化学和取代基的东方特征，以及这种化合物的结构和反应活性的相关性。初步的生物分析表明，几种化合物具有良好的杀虫活性，其中12c对Mythimna separata Walker的致死率为200μg/ mL，杀灭率为80％。一些化合物在50μg/ mL的浓度下对皮毛小孢子菌（Physalospora piricola）表现出有利的杀真菌活性，谷物纹枯病菌，核盘菌菌核等，其中12a，12b，12c和12h可以被认为是新的杀真菌主导化合物，可进一步优化结构。这些发现以及本文中的结构-活性关系分析将为新的吡啶基吡唑衍生物的创新研究及其在农业化学领域中的应用提供有益的指导。
• 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