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

Abstract

The discovery of sulfoxaflor [N-[methyloxido[1-[6-(trifluoromethyl)-3-pyridinyl]ethyl]-λ(4)-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.

Overall status of neonicotinoid insecticides in China: Production, application and innovation

“…12) Sulfoxaflor, the newest neonicotinoid discovered by Dow AgroSciences, acts on nAChRs as an agonist. 13,14) It exhibits high potency and lacks insecticidal cross-resistance; thus it could be used as an alternative to control sap-feeding insect pests. 15) It is expected to be introduced in 2013 in China as long as the registrations are granted.…”

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides

“…Their expanding application in drug design is exemplified in compound AZD6738 from AstraZeneca 8, 9. Moreover, since their discovery in the form of MSO,10 sulfoximines have been developed as ligands and auxiliaries for asymmetric synthesis11, 12 and directing groups in C−H functionalization,13, 14 as well as used in agrochemical agents such as sulfoxaflor 15…”

Design, synthesis, crystal structure, bioactivity, and molecular docking studies of novel sulfonylamidine-derived neonicotinoid analogs

“…Modification of the structures of existing neonicotinoids can be an effective tactic to combat resistance. For example, sulfoximines have proved to be useful structural motifs in active, non-cross-resistant insecticides, and may be involved in recognition and interactions with the insect target (Loso et al, 2008;Zhu et al, 2010;Yu et al, 2008;Zhu et al, 2011). As shown in Fig.…”