title: Design, synthesis and insecticidal evaluation of aryloxy dihalopropene derivatives.
abstract: Plutella xylostella (P. xylostella) is a highly migratory, cosmopolitan species and one of the most important pest of cruciferous crops worldwide. Pyridalyl as a novel class of insecticides has good efficacy against P. xylostella. On the basis of the commercial insecticide pyridalyl, a series of new aryloxy dihalopropene derivatives were designed and synthesized by using Intermediate Derivatization Methods. Their chemical structures were confirmed by (1)H NMR, high-resolution mass spectrum (HRMS), and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds against P. xylostella were evaluated. The results of bioassays indicated that most of the compounds showed moderate to high activities at the tested concentration, especially compounds 10e and 10g displayed more than 75% insecticidal activity against P. xylostella at 6.25mg/L, while pyridalyl showed 50% insecticidal activity at the same concentration. The field trials result of the insecticidal activities showed that compound 10e as a 10% emulsifiable concentrate (EC) was effective in the control of P. xylostella at 75-150g a.i./ha, and the mortality of P. xylostella for treatment with compound 10e at 75g a.i./ha was equivalent to pyridalyl at 105g a.i./ha.
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd, Shenyang 110021, China.
authors.forename: Ji-Chun
authors.initials: JC
authors.lastname: Yang
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd, Shenyang 110021, China.
authors.forename: Miao
authors.initials: M
authors.lastname: Li
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd, Shenyang 110021, China.
authors.forename: Qiao
authors.initials: Q
authors.lastname: Wu
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd, Shenyang 110021, China. Electronic address: liuchangling@vip.163.com.
authors.forename: Chang-Ling
authors.initials: CL
authors.lastname: Liu
authors.affiliation: State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd, Shenyang 110021, China.
authors.forename: Xiu-Hui
authors.initials: XH
authors.lastname: Chang
mesh_terms: D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009036:Moths / Q000187:drug effects*; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000611442:2-(4-(3-(2,6-dichloro-4-((3,3-dichloroallyl)oxy)phenoxy)propoxy)phenoxy)-5-(trifluoromethyl)pyridine; C000611443:3-chloro-2-(4-(3-(2,6-dichloro-4-((3,3-dichloroallyl)oxy)phenoxy)propoxy)phenoxy)-5-(trifluoromethyl)pyridine; D000498:Allyl Compounds; D007306:Insecticides; D011725:Pyridines
keywords: Aryloxy dihalopropene derivatives; Insecticidal activities; Intermediate Derivatization Methods (IDM); Structure–activity relationship