{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,7,3]],"date-time":"2025-07-03T04:15:14Z","timestamp":1751516114165,"version":"3.41.0"},"reference-count":37,"publisher":"Public Library of Science (PLoS)","issue":"7","license":[{"start":{"date-parts":[[2025,7,2]],"date-time":"2025-07-02T00:00:00Z","timestamp":1751414400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["www.plosone.org"],"crossmark-restriction":false},"short-container-title":["PLoS One"],"abstract":"<jats:p>The acaricide propargite has been widely used for over 50 years without significant resistance issues. Addressing to the propargite defects of poor crop safety, thirty-six novel halogenated propargite analogues were designed, synthesized, and characterized using <jats:sup>1<\/jats:sup>H NMR, <jats:sup>13<\/jats:sup>C NMR spectroscopy, and HRMS. All target compounds were screened for activity against adult <jats:italic>Tetranychus cinnabarinus<\/jats:italic> (spider mites) and <jats:italic>Myzus persicae<\/jats:italic> (aphids). Two compounds exhibiting higher insecticidal activity were further evaluated for crop safety on cowpea seedlings. Structural modifications, such as replacing the <jats:italic>tert<\/jats:italic>-butyl group on the propargite benzene ring with chlorine or trifluoromethoxy, and substituting the propargyl group with fluorinated alkyl groups (e.g., 2-fluoroethyl or 3,3,3-trifluoropropyl), significantly enhanced both acaricidal and aphicidal activity. Compound <jats:bold>5.16<\/jats:bold> demonstrated superior acaricidal activity (LC<jats:sub>50<\/jats:sub>: 14.85\u2009mg L<jats:sup>-1<\/jats:sup>) on <jats:italic>Tetranychus cinnabarinus<\/jats:italic> and excellent crop safety on cowpea seedlings. Additionally, Compound <jats:bold>5.32<\/jats:bold> exhibited both acaricidal (LC<jats:sub>50<\/jats:sub>: 14.32\u2009mg L<jats:sup>-1<\/jats:sup>) and aphicidal activity, which is unusual in this chemical class. The compounds <jats:bold>5.16<\/jats:bold> and <jats:bold>5.32<\/jats:bold> could be used as promising leads for the discovery of novel acaricides or insecticides.<\/jats:p>","DOI":"10.1371\/journal.pone.0327587","type":"journal-article","created":{"date-parts":[[2025,7,2]],"date-time":"2025-07-02T17:47:32Z","timestamp":1751478452000},"page":"e0327587","update-policy":"https:\/\/doi.org\/10.1371\/journal.pone.corrections_policy","source":"Crossref","is-referenced-by-count":0,"title":["Design, synthesis, and biological activity of novel halogenated sulfite 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