SAR Studies Directed Toward the Pyridine Moiety of the Sap-Feeding Insecticide Sulfoxaflor (Isoclast™ active)

Publication date: Available online 22 November 2015
Source:Bioorganic & Medicinal Chemistry
Author(s): Michael R. Loso, Zoltan Benko, Ann Buysse, Timothy C. Johnson, Benjamin M. Nugent, Richard B. Rogers, Thomas C. Sparks, Nick X. Wang, Gerald B. Watson, Yuanming Zhu
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 sulfoximines 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 log octanol/water partition coefficient (SLogP). Model development resulted in a highly predictive model for a set of 18 sufoximines including sulfoxaflor. The model is consistent with and helps explain the highly optimized pyridine substitution pattern for sulfoxaflor.

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