Discovery and Characterization of Sulfoxaflor, a Novel Insecticide Targeting Sap-Feeding Pests

• Published in: Journal of agricultural and food chemistry Vol. 59; no. 7; pp. 2950 - 2957
• Main Authors: Zhu, Yuanming, Loso, Michael R, Watson, Gerald. B, Sparks, Thomas C, Rogers, Richard B, Huang, Jim X, Gerwick, B. Clifford, Babcock, Jonathan M, Kelley, Donald, Hegde, Vidyadhar B, Nugent, Benjamin M, Renga, James M, Denholm, Ian, Gorman, Kevin, DeBoer, Gerrit J, Hasler, James, Meade, Thomas, Thomas, James D
• Format: Journal Article Conference Proceeding
• Language: English
• Published: Washington, DC American Chemical Society 13-04-2011
• Subjects: aerobiosis; Aleyrodidae; Animals; Aphidoidea; Aphids; Biological and medical sciences; cross resistance; Food industries; Fundamental and applied biological sciences. Psychology; Hemiptera; imidacloprid; Imidazoles; insect control; insect pests; Insecta; insecticidal properties; Insecticide Resistance; Insecticides - chemistry; Lygus; Neonicotinoids; Nitro Compounds; Pyridines - chemistry; Receptors, Nicotinic; Structure-Activity Relationship; Sulfur Compounds - chemistry; sulfoximines; insecticide resistance; Myzus persicae; sulfoxaflor; nicotinic acetylcholine receptor; Insecticide; Sap; Targeting; Pesticides; Discoveries; Feeding; Characterization; Resistance; Cholinergic receptor; Pest; Nicotinic receptor
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf102765x

The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ4-sulfanylidene] cyanamide] resulted from an investigation of the sulfoximine functional group as a novel bioactive scaffold for insecticidal activity and a subsequent extensive structure−activity relationship study. Sulfoxaflor, the first product from this new class (the sulfoximines) of insect control agents, exhibits broad-spectrum efficacy against many sap-feeding insect pests, including aphids, whiteflies, hoppers, and Lygus, with levels of activity that are comparable to those of other classes of insecticides targeting sap-feeding insects, including the neonicotinoids. However, no cross-resistance has been observed between sulfoxaflor and neonicotinoids such as imidacloprid, apparently the result of differences in susceptibility to oxidative metabolism. Available data are consistent with sulfoxaflor acting via the insect nicotinic receptor in a complex manner. These observations reflect the unique structure of the sulfoximines compared with neonicotinoids.