title: Synthesis and biological activity evaluation of novel β-substituted nitromethylene neonicotinoid analogues.
abstract: The structure-based design and synthesis of a series of novel neonicotinoid analogues are described. The novel neonicotinoid analogues were designed based upon the reaction of enamine derivatives with electron-withdrawing β-substituents with electrophilic thiocyanogen reagents. These compounds were characterized by spectroscopic methods. Bioassays indicated that some of the synthesized compounds exhibited excellent bioactivity against cowpea aphids (Aphis craccivora). The LC₅₀ values of compounds 7, 9,12, 13, 15, 17, 19, 20 and commercial imidacloprid were 0.01567, 0.00974, 0.02494, 0.01893, 0.02677, 0.01778, 0.0220, 0.02447 and 0.03502 mmol L⁻¹, respectively, which suggested that they could be used as leads for future development of new insecticides.
authors.affiliation: Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, P.O. Box 544, 130 Meilong Road, Shanghai 200237, China. lizhong@ecust.edu.cn.
authors.forename: Baozhu
authors.initials: B
authors.lastname: Wang
authors.forename: Jiagao
authors.initials: J
authors.lastname: Cheng
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Xu
authors.forename: Xiaoyong
authors.initials: X
authors.lastname: Xu
authors.forename: Xusheng
authors.initials: X
authors.lastname: Shao
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
mesh_terms: D000691:Anabasine / Q000031:analogs & derivatives* / Q000737:chemistry; D000818:Animals; D001042:Aphids; D007093:Imidazoles / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry; D009595:Nitroparaffins / Q000737:chemistry*; D013861:Thiocyanates / Q000737:chemistry
chemical_list: D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; D009595:Nitroparaffins; D013861:Thiocyanates; C082359:imidacloprid; D000691:Anabasine; C031760:thiocyanate; D008697:Methane; C008640:nitromethane