title: Synthesis and Insecticidal Activity of Novel Nitropyridyl-Based Dichloropropene Ethers.
abstract: Dihalopropene ether insecticides are known for good features such as no cross-resistance to other insecticide classes and safety for mammals. Pyridalyl is the only currently commercialized dichloropropene ether insecticide; however, it contains a trifluoromethyl group, the synthesis of which requires harsh reagents and reaction conditions. To search for novel dihalopropene ethers with unique biological activities but without trifluoromethyl groups, a series of nitropyridyl-based dichloropropene ether analogues were synthesized by reacting nitro-based halopyridine with 2,6-dichloro-4-(3,3-dichloroallyloxy)phenol or 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-hydroxypropyl ether. Bioassay showed that the compounds exhibited potent insecticidal activities against various lepidopteran pests. Particularly, 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-(5-nitro-2-pyridyloxy)propyl ether (8e) was active against major agricultural pests, and its insecticidal potency was comparable to that of Pyridalyl. Besides the trifluoromethyl group in Pyridalyl, a nitro group on the 5-position of the pyridyl ring is also viable for the development of optimal insecticidal activity.
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.|Hunan Province Key Laboratory for Agrochemicals , Changsha 410014, People's Republic of China.
authors.forename: Aiping
authors.initials: A
authors.lastname: Liu
authors.affiliation: Department of Chemistry, Carleton College , Northfield, Minnesota 55057, United States.
authors.forename: Wanqi
authors.initials: W
authors.lastname: Yu
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Minhua
authors.initials: M
authors.lastname: Liu
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Jianjun
authors.initials: J
authors.lastname: Bai
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Weidong
authors.initials: W
authors.lastname: Liu
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Xingping
authors.initials: X
authors.lastname: Liu
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Hui
authors.initials: H
authors.lastname: Pei
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Li
authors.initials: L
authors.lastname: Hu
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.|Hunan Haili Chemical Industry Company Ltd., Changsha 410007, People's Republic of China.
authors.forename: Mingzhi
authors.initials: M
authors.lastname: Huang
authors.affiliation: National Engineering Research Center for Agrochemicals, Hunan Research Institute of Chemical Industry , Changsha 410007, People's Republic of China.
authors.forename: Xiaoguang
authors.initials: X
authors.lastname: Wang
mesh_terms: D000818:Animals; D004987:Ethers / Q000737:chemistry / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects; D009574:Nitro Compounds / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004987:Ethers; D007306:Insecticides; D009574:Nitro Compounds; C045122:propyl ether
keywords: insecticide; nitropyridyl-based dichloropropene ethers; structure−activity relationship; synthesis