title: Synthesis, insecticidal activity, and molecular docking studies of nitenpyram analogues with a flexible ester arm anchored on tetrahydropyrimidine ring.
abstract: To make further researches on the structure-activity relationships (SARs) of our previous synthesized neonicotinoid compounds, a new series of nitenpyam analogues with flexible ester arm were synthesized. Preliminary bioassays indicated that all of our newly designed nitenpyam analogues exhibited good insecticidal activity at 100 mg/L, while analogues 4c and 4d afforded the best in vitro activity, and both of them had 100% mortality at 20 mg/L. The SAR studies suggested that their insecticidal potency was dual-controlled by the length of the ester arm and the size of the ester group. In addition, the molecular docking simulations revealed that the structural uniqueness of these analogues may lead to a unique molecular recognition and binding mode, which explained the SARs observed in vitro, and shed light on the novel insecticidal mechanism of these novel nitenpyam analogues.
authors.affiliation: College of Life and Environment Sciences, Shanghai Normal University, Shanghai, China. willin112@163.com
authors.forename: Chuanwen
authors.initials: C
authors.lastname: Sun
authors.forename: Xiao
authors.initials: X
authors.lastname: Xu
authors.forename: Yonghua
authors.initials: Y
authors.lastname: Xu
authors.forename: Dingrong
authors.initials: D
authors.lastname: Yan
authors.forename: Ting
authors.initials: T
authors.lastname: Fang
authors.forename: Tianyan
authors.initials: T
authors.lastname: Liu
mesh_terms: D000818:Animals; D007313:Insecta / Q000187:drug effects; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000073943:Neonicotinoids; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D000073943:Neonicotinoids; D011725:Pyridines; C464843:nitenpyram