文献类型：期刊文献

英文题名：Discovery of Novel Neonicotinoids with Conjugated Diene Enabled by Cascade Allylation/Isomerization Synthetic Methodology

作者：Zhang, Dongxu[1,2];Zhou, Cong[1,2];Qi, Suzhen[3];Zhang, Huihui[4];Shao, Xusheng[1,2];Xu, Xiaoyong[1,2];Cheng, Jiagao[1,2];Liu, Zewen[4];Li, Zhong[1,2];Yang, Wu-Lin[1,2]

机构：[1]East China Univ Sci & Technol, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China;[3]Chinese Acad Agr Sci, Inst Apicultural Res, Beijing 100093, Peoples R China;[4]Nanjing Agr Univ, Coll Plant Protect, Key Lab Integrated Management Crop Dis & Pests, Minist Educ, Nanjing 210095, Peoples R China

年份：2025

卷号：73

期号：5

起止页码：2784

外文期刊名：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

收录：;EI(收录号：20250517775422);WOS:【SCI-EXPANDED(收录号:WOS:001403562500001)】；

基金：This work was supported by the Shanghai Agriculture Applied Technology Development Program (T2023309), the National Natural Science Foundation of China (22171081 and 22477027), the Shanghai Rising-Star Program (23QA1402600), the Natural Science Foundation of Shanghai Municipality (23ZR1416700), and the Shanghai Agricultural Science and Technology Innovation Project (K2023020). The authors thank the Research Center of Analysis and Test of East China University of Science and Technology for help with HRMS and NMR analyses.

语种：英文

外文关键词：neonicotinoid insecticides; insect resistance; bee toxicity; conjugated system; insecticidal activity; cascade reaction

摘要：As one of the most significant insecticides, neonicotinoids have played a pivotal role in crop protection and public sanitation. However, the high resistance and bee toxicity of neonicotinoid insecticides have attracted considerable attention. Herein, a series of neonicotinoid compounds with conjugated diene moieties were synthesized through the cascade allylation/isomerization reaction. Most of the target compounds exhibited excellent insecticidal activities against Aphis craccivora, and some compounds exhibited good insecticidal activities against Mythimna separata. In particular, compound A15 showed outstanding insecticidal activity against A. craccivora (LC50 = 0.15 mg/L), which was superior to that of imidacloprid (LC50 = 0.36 mg/L). In addition, this candidate exhibited minimal cross-resistance to imidacloprid. The acute contact toxicity tests on Apis mellifera suggested that compound A15 was 10 times less toxic than imidacloprid. Electrophysiological experiments and molecular docking studies indicated that compound A15 exerted its insecticidal effects by interfering with nicotinic acetylcholine receptors. This work identifies a novel conjugated diene neonicotinoid candidate with significant potential for further development.