title: Design, synthesis, crystal structure analysis, and insecticidal evaluation of phenylazoneonicotinoids.
abstract: On the basis of research of the proposed modes of action between neonicotinoids and insect nicotinic acetylcholine receptor (nAChR), a series of phenylazoneonicotinoids were designed and synthesized to further promote the π-π interaction between molecule and amino acid residues. The target compounds have been identified on the basis of satisfactory analytical and spectral ((1)H NMR, (13)C NMR, HRMS, and X-ray) data. The preliminary results revealed that tiny differences in substitutes resulted in different configurations and great bioactivity variations. Some compounds with electron-donating groups on positions 2 and 6 of the phenyl ring presented higher insecticidal activity than imidacloprid against cowpea aphids ( Aphis craccivora ). The impressive crystal structure of the excellent insecticidal activity compound 9q clearly proved that the functional electronegative pharmacophore was approximately vertical to the methyleneimidazolidine plane. The differences in the mode of interaction on nAChR of typical compounds 9h and 9q remain unclear.
authors: Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology , Shanghai 200237, China.
authors: Zhenjun
authors: Z
authors: Ye
authors: Shuang
authors: S
authors: Xia
authors: Xusheng
authors: X
authors: Shao
authors: Jiagao
authors: J
authors: Cheng
authors: Xiaoyong
authors: X
authors: Xu
authors: Zhiping
authors: Z
authors: Xu
authors: Zhong
authors: Z
authors: Li
authors: Xuhong
authors: X
authors: Qian
mesh_terms: D000691:Anabasine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D000818:Animals; D001042:Aphids; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003460:Crystallization; D007313:Insecta / Q000737:chemistry; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D011978:Receptors, Nicotinic; D013329:Structure-Activity Relationship
chemical_list: C569569:2-chloro-5-(((E)-2-(((E)-(2,6-dimethylphenyl)diazenyl)(nitro)methylene)imidazolidin-1-yl)methyl)pyridine; D001391:Azo Compounds; D007306:Insecticides; D011978:Receptors, Nicotinic; D000691:Anabasine