title: Expanding the structure-activity relationship of sulfoxaflor: the synthesis and biological activity of N-heterocyclic sulfoximines.
abstract: BACKGROUND
  Sulfoxaflor, a new insect control agent developed by Dow AgroSciences, exhibits broad-spectrum control of many sap-feeding insect pests, including aphids, whiteflies, leafhoppers, planthoppers and lygus bugs. During the development of sulfoxaflor, structure-activity relationship (SAR) exploration of the sulfoximine functional group revealed that the nature of the sulfoximine nitrogen substituent significantly affects insecticidal acitivity. As part of the investigation to probe the various electronic, steric and lipophilic parameters at this position, a series of N-heterocyclic sulfoximines were synthesized and tested for bioactivity against green peach aphid.
  
  
  RESULTS
  Using a variety of chemistries, the nitrile substituent was replaced with different substituted five- and six-membered heterocycles. The compounds in the series were then tested for insecticidal acitivty against green peach aphid in foliar spray assays. In spite of the larger steric demand of these substituents, the resulting N-heterocyclic sulfoximine analogs displayed good levels of efficacy. In particular, the N-thiazolyl sulfoximines exhibited the greatest activity, with LC50 values as low as 1 ppm.
  
  
  CONCLUSIONS
  The novel series of N-heterocyclic sulfoximines helped to advance the current knowledge of the sulfoxaflor SAR, and demonstrated that the structural requirement for the sulfoximine nitrogen position was not limited to small, electron-deficient moeities, but rather was tolerant of larger functionality.
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Benjamin M
authors: BM
authors: Nugent
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Ann M
authors: AM
authors: Buysse
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Michael R
authors: MR
authors: Loso
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Jon M
authors: JM
authors: Babcock
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Timothy C
authors: TC
authors: Johnson
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: M Paige
authors: MP
authors: Oliver
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Timothy P
authors: TP
authors: Martin
authors: The Dow Chemical Company, 2030 Dow Center, Midland, MI, USA.
authors: Matthias S
authors: MS
authors: Ober
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Nneka
authors: N
authors: Breaux
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Andrew
authors: A
authors: Robinson
authors: R&D, Dow AgroSciences, 9330 Zionsville Road, Indianapolis, IN, USA.
authors: Yelena
authors: Y
authors: Adelfinskaya
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects*; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D007306:Insecticides; D011725:Pyridines; D013457:Sulfur Compounds; C560328:sulfoxaflor
keywords: Myzus persicae; green peach aphid; insecticide; structure-activity relationship; sulfilimine; sulfoxaflor