Divalent and oxabridged neonicotinoids constructed by dialdehydes and nitromethylene analogues of imidacloprid: design, synthesis, crystal structure, and insecticidal activities.
A series of divalent and oxabridged neonicotinoids were synthesized by reactions of nitromethylene analogues of imidacloprid and dialdehydes, and their structures were confirmed by (1)H NMR, (13)C NMR, high-resolution mass spectroscopy, and X-ray diffraction analysis. The bioassays indicated that some of them were endowed with excellent insecticidal activities against cowpea aphid ( Aphis craccivora ), armyworm ( Pseudaletia separata Walker), and brown planthopper ( Nilaparvata lugens ). Divalent neonicotinoid 6 and oxabridged 8a had higher activities than imidacloprid against cowpea aphids and armyworm; furthermore, the activity of 8a was 40.4-fold higher than that of imidacloprid against imidacloprid-resistant brown planthopper.
Shao
Xusheng
X
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Fu
Hua
H
Xu
Xiaoyong
X
Xu
Xinglei
X
Liu
Zewen
Z
Li
Zhong
Z
Qian
Xuhong
X
D000818:Animals; D001042:Aphids; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000737:chemistry*; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D009036:Moths; D000073943:Neonicotinoids; D009538:Nicotine / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009574:Nitro Compounds / Q000737:chemistry*
D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; C082359:imidacloprid; D009538:Nicotine