Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group

• Published in: Molecules (Basel, Switzerland) Switzerland), 2017-06, Vol.22 (6), p.958
• Main Authors: Sun, Guo-Shao, Xu, Xin, Jin, Shu-Hui, Lin, Le, Zhang, Jian-Jun
• Format: Article
• Language: English
• Subjects: Animals; Aphids - drug effects; Aphids - pathogenicity; Benzaldehyde; Biological activity; Carboxylic acids; Carboxylic Acids - chemistry; Carboxylic Acids - pharmacology; Eggs; Esters - chemical synthesis; Esters - chemistry; Esters - pharmacology; insecticidal activity; Insecticides - chemical synthesis; Insecticides - chemistry; Insecticides - pharmacology; Ionization; Ions; Magnetic Resonance Spectroscopy; Mass spectrometry; Mass spectroscopy; Molecular Structure; Moths - drug effects; Moths - pathogenicity; Myzus persicae; NMR; Nuclear magnetic resonance; ovicidal activity; oxime ester derivatives; Oximes - chemical synthesis; Oximes - chemistry; Oximes - pharmacology; Pyridines - chemical synthesis; Pyridines - chemistry; Pyridines - pharmacology; Pyriproxyfen; pyriproxyfen metabolite; Spectrometry, Mass, Electrospray Ionization; Structure-Activity Relationship
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules22060958

Based on the structural framework of a pyriproxyfen metabolite, nineteen oxime ester derivatives were synthesized via reaction of the carboxylic acids with 4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime. The corresponding structures were comprehensively characterized by ¹H-nuclear magnetic resonance (NMR), C-NMR, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS). All of the compounds were screened for their insecticidal activities against and , and for their ovicidal activities against eggs. The results obtained show that most of the oxime ester derivatives displayed moderate to high insecticidal activities and ovicidal activities at a concentration of 600 ug/mL. In particular, the ovicidal activity of compounds , , , , and was determined to be 100%. Importantly, some of the compounds presented even higher biological activities than the reference compound pyriproxyfen. For example, compound displayed an insecticidal activity value of 87.5% against , whereas the activity value of pyriproxyfen was 68.3% at a concentration of 600 ug/mL. Among the synthesized compounds and exhibited broad biological activity spectra.