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

[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 man...

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Veröffentlicht in:Bioorganic & medicinal chemistry 2016-02, Vol.24 (3), p.378-382
Hauptverfasser: 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
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Sprache:eng
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Zusammenfassung:[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.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2015.11.022