Design, Synthesis, and Acaricidal Activity of Phenyl Methoxyacrylates Containing 2-Alkenylthiopyrimidine

A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR and...

Full description

Bibliographic Details
Main Authors: Shulin Hao, Zengfei Cai, Yangyang Cao, Xiaohua Du
Format: Article
Language:English
Published: MDPI AG 2020-07-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/15/3379
Description
Summary:A series of novel phenyl methoxyacrylate derivatives containing a 2-alkenylthiopyrimidine substructure were designed, synthesized, and evaluated in terms of acaricidal activity. The structures of the title compounds were identified by <sup>1</sup>H NMR, <sup>13</sup>C NMR and high-resolution mass spectra (HRMS). Compound (<i>E</i>)-methyl 2-(2-((2-(3,3-dichloroallylthio)-6-(trifluoromethyl)pyrimidin-4-yloxy)methyl)phenyl)-3-methoxyacr-ylate (<b>4j</b>) exhibited significant acaricidal activity against <i>Tetranychus cinnabarinus</i> (<i>T. cinnabarinus</i>) in greenhouse tests possessing nearly twice the larvicidal and ovicidal activity compared to fluacrypyrim. Furthermore, the results of the field trials demonstrated that compound <b>4j</b> could effectively control <i>Panonychuscitri</i> with long-lasting persistence and rapid action. The toxicology data in terms of LD<sub>50</sub> value confirmed that compound <b>4j</b> has a relatively low acute toxicity to mammals, birds, and honeybees.
ISSN:1420-3049