SAR studies directed toward the pyridine moiety of the sap-feeding insecticide sulfoxaflor (Isoclast™ active)

• Published in: Bioorganic & medicinal chemistry Vol. 24; no. 3; pp. 378 - 382
• Main Authors: Loso, Michael R., Benko, Zoltan, Buysse, Ann, Johnson, Timothy C., Nugent, Benjamin M., Rogers, Richard B., Sparks, Thomas C., Wang, Nick X., Watson, Gerald B., Zhu, Yuanming
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01.02.2016
• Subjects: Animals; Aphids - drug effects; Dose-Response Relationship, Drug; Insecticide; Insecticides - chemistry; Insecticides - pharmacology; Isoclast; Molecular Structure; Pyridines - chemistry; Pyridines - pharmacology; Sap-feeding; Structure activity relationship; Sulfoxaflor; Sulfur Compounds - chemistry; Sulfur Compounds - pharmacology; Sulfoxaflor; Structure activity relationship; Insecticide; Sap-feeding; Isoclast
• DOI: 10.1016/j.bmc.2015.11.022
• ISSN: 0968-0896

[Display omitted] Sap-feeding insect pests constitute a major insect pest complex that includes a range of aphids, whiteflies, planthoppers and other insect species. Sulfoxaflor (Isoclast™ active), a new sulfoximine class insecticide, targets sap-feeding insect pests including those resistant to many other classes of insecticides. A structure activity relationship (SAR) investigation of the sulfoximine insecticides revealed the importance of a 3-pyridyl ring and a methyl substituent on the methylene bridge linking the pyridine and the sulfoximine moiety to achieving strong Myzus persicae activity. A more in depth QSAR investigation of pyridine ring substituents revealed a strong correlation with the calculated logoctanol/water partition coefficient (SlogP). Model development resulted in a highly predictive model for a set of 18 sulfoximines including sulfoxaflor. The model is consistent with and helps explain the highly optimized pyridine substitution pattern for sulfoxaflor.