cis-Configuration: a new tactic/rationale for neonicotinoid molecular design.
Resistance development and limited lepidopteran activities call for the discovery of "super-neonicotinoids" solving these problems. Compounds with the cis-configuration offer an opportunity for further optimization. Fixing the nitro group in the cis-configuration provided a new approach for neonicotinoid molecular design. Introductions of the heterocycle or a bulky group are two synthesis concepts to fix the cis-configuration of the nitro group. The design, synthesis, bioactivity, and preliminary modes of action of five types of cis-neonicotinoids are reviewed. cis- and trans-neonicotinoids have some differences in bioactivities and modes of action. This study focused, especially, on the reaction diversities of nitromethylene analogues of imidacloprid with various aldehydes.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China.
Xusheng
X
Shao
Philip W
PW
Lee
Zewen
Z
Liu
Xiaoyong
X
Xu
Zhong
Z
Li
Xuhong
X
Qian
D000691:Anabasine / Q000819:agonists*; D000818:Animals; D015195:Drug Design; D007093:Imidazoles; D007305:Insecticide Resistance; D007306:Insecticides / Q000737:chemistry*; D007915:Lepidoptera; D008968:Molecular Conformation; D000073943:Neonicotinoids; D009574:Nitro Compounds; D013329:Structure-Activity Relationship
D007093:Imidazoles; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; C082359:imidacloprid; D000691:Anabasine