Chen Shilin, Zhang Yu, Liu Yuxiu, Wang Qingmin
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, People's Republic of China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, People's Republic of China.
J Agric Food Chem. 2021 Mar 31;69(12):3601-3606. doi: 10.1021/acs.jafc.0c05558. Epub 2021 Mar 19.
Nitrogen heterocycles are found in numerous natural products, pharmaceuticals, and pesticides. Herein, we report the design and synthesis of a series of novel 2,4-diphenyl-1,3-oxazolines bearing various N-heterocyclic substituents via a 4-(4-(chloromethyl)phenyl)-2-(2,6-difluorophenyl)-4,5-dihydrooxazole intermediate generated by a modified Ritter reaction. Evaluation of the activities of the oxazolines against carmine spider mites () by means of a leaf-dipping method showed that most of the compounds exhibited good to excellent larvicidal and ovicidal activities. In particular, five compounds (one with a phthalimidyl group and four with a substituted indolyl group) have lower LC values than the commercial acaricide etoxazole (0.088 mg/L against larvae and 0.128 mg/L against eggs). This work lays a foundation for the development of novel acaricides.
氮杂环存在于众多天然产物、药物和农药中。在此，我们报道了一系列带有各种N - 杂环取代基的新型2,4 - 二苯基 - 1,3 - 恶唑啉的设计与合成，该合成通过一种经改进的 Ritter 反应生成的4-(4-(氯甲基)phenyl)-2-(2,6 - 二氟苯基)-4,5 - 二氢恶唑中间体进行。通过浸叶法评估恶唑啉对朱砂叶螨的活性表明，大多数化合物表现出良好至优异的杀幼虫和杀卵活性。特别地，五种化合物（一种带有邻苯二甲酰亚胺基，四种带有取代吲哚基）的LC值低于市售杀螨剂乙螨唑（对幼虫为0.088 mg/L，对卵为0.128 mg/L）。这项工作为新型杀螨剂的开发奠定了基础。
