title: Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.
abstract: Versatile pyrrole- and dihydropyrrole-fused neonicotinoids were obtained from cyclic and non-cyclic nitroeneamines. Anhydrous aluminum chloride (AlCl₃) exhibited high catalytic selectivity for the synthesis of the titled etherified compounds at room temperature and the eliminated products under reflux conditions. The target molecules have been identified on the basis of satisfactory analytical and spectral [¹H and ¹³C nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and X-ray] data. All synthesized compounds have been screened for insecticidal activity. The preliminary insecticidal activity results showed that some of the aimed compounds displayed excellent insecticidal activity against cowpea aphids (Aphis craccivora).
authors.affiliation: Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, People's Republic of China.
authors.forename: Zhenjun
authors.initials: Z
authors.lastname: Ye
authors.forename: Lina
authors.initials: L
authors.lastname: Shi
authors.forename: Xusheng
authors.initials: X
authors.lastname: Shao
authors.forename: Xiaoyong
authors.initials: X
authors.lastname: Xu
authors.forename: Zhiping
authors.initials: Z
authors.lastname: Xu
authors.forename: Zhong
authors.initials: Z
authors.lastname: Li
mesh_terms: D000691:Anabasine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D001042:Aphids; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry; D007928:Lethal Dose 50; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D011758:Pyrroles; C013231:pyrroline; D000691:Anabasine