title: Discovery of a novel series of phenyl pyrazole inner salts based on fipronil as potential dual-target insecticides.
abstract: A series of novel phenyl pyrazole inner salt derivatives based on fipronil were designed and synthesized in the search for dual-target insecticides. These compounds were designed to target two families of nicotinic acetylcholine receptors and γ-aminobutyric acid receptors. The insecticidal activities of the new compounds against diamondback moth (Plutella xylostella) were evaluated. The results of bioassays indicated that most of the inner salts showed moderate to high activities, of which the phenyl pyrazole inner salts containing quinoline had excellent biological activity. Previous structure-activity relationship studies revealed that a suitable structure of the quaternary ammonium salts was critical for the bioactivity of phenyl pyrazole inner salts, which contribute to exposing the cationic nitrogen to bind to the receptor (for instance, nicotinic acetylcholine receptors) and possibly interact with the receptor via hydrogen bonding and cooperative π-π interaction. The present work demonstrates that the insecticidal potency of phenyl pyrazole inner salts holds promise for the development new dual-target phenyl pyrazole insecticides.
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, Laboratory of Insect Toxicology, South China Agricultural University , Guangzhou 510642, People's Republic of China.
authors.forename: Dingxin
authors.initials: D
authors.lastname: Jiang
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Zheng
authors.forename: Guang
authors.initials: G
authors.lastname: Shao
authors.forename: Zhang
authors.initials: Z
authors.lastname: Ling
authors.forename: Hanhong
authors.initials: H
authors.lastname: Xu
mesh_terms: D000818:Animals; D015195:Drug Design; D007306:Insecticides / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D011720:Pyrazoles / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D007306:Insecticides; D011720:Pyrazoles; C031280:pyrazole; C082360:fipronil