SAR studies directed toward the pyridine moiety of the sap-feeding insecticide sulfoxaflor (Isoclast™ active). Issue 3 (1st February 2016)

• Record Type: Journal Article
• 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
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 3(2016)
• Page Start: 378
• Page End: 382
• Publication Date: 2016-02-01
• Subjects: Isoclast -- Sulfoxaflor -- Sap-feeding -- Insecticide -- Structure activity relationship; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.11.022
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: Abstract: 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 log octanol/water partition coefficient ( S log P ). 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.