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

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 st...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2011-04, Vol.59 (7), p.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: Article
Language:English
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
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Summary: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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf102765x