Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: replacement of nitromethylene with nitroconjugated system.
To replace nitromethylene pharmacophore with a nitroconjugated system, a series of novel neonicotinoid analogues bearing five-membered aromatic heterocycles were designed and synthesized. Bioassays indicated that some of the synthesized compounds exhibited higher insecticidal activities than imidacloprid against cowpea aphids ( Aphis craccivora ), armyworm ( Pseudaletia separate Walker), Nephotettix bipunctatus (Fabricius), and small brown rice planthopper ( Laodelphasx striatellus ). Exhilaratingly, the activity levels of derivatives 13a and 13j rivaled that of imidacloprid.
Shao
Xusheng
X
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China.
Li
Zhong
Z
Qian
Xuhong
X
Xu
Xiaoyong
X
D000691:Anabasine / Q000737:chemistry*; D000818:Animals; D001042:Aphids; D015195:Drug Design; D006430:Hemiptera; D007093:Imidazoles; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry; D009036:Moths; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000737:chemistry*; D011978:Receptors, Nicotinic
D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; D011978:Receptors, Nicotinic; C082359:imidacloprid; D000691:Anabasine