Expanding the structure–activity relationship of sulfoxaflor: the synthesis and biological activity of N‐heterocyclic sulfoximines1. Issue 7 (10th September 2014)

• Record Type: Journal Article
• Authors: Nugent, Benjamin M; Buysse, Ann M; Loso, Michael R; Babcock, Jon M; Johnson, Timothy C; Oliver, M Paige; Martin, Timothy P; Ober, Matthias S; Breaux, Nneka; Robinson, Andrew; Adelfinskaya, Yelena
• Is Part Of: Pest management science. Volume 71:Issue 7(2015:Jul.)
• Page Start: 928
• Page End: 936
• Publication Date: 2014-09-10
• Subjects: Pests -- Control -- Periodicals; Pesticides -- Periodicals; 632.9
• DOI: 10.1002/ps.3865
• Languages: English
• ISSNs: 1526-498X

Abstract

<abstract abstract-type="main" id="ps3865-abs-0001"> <title>Abstract</title> <sec id="ps3865-sec-0001" sec-type="section"> <title>BACKGROUND</title> <p id="ps3865-para-0001">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 <italic>N</italic>‐heterocyclic sulfoximines were synthesized and tested for bioactivity against green peach aphid.</p> </sec> <sec id="ps3865-sec-0002" sec-type="section"> <title>RESULTS</title> <p id="ps3865-para-0002">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 <italic>N</italic>‐heterocyclic sulfoximine analogs displayed good levels of efficacy. In particular, the <italic>N</italic>‐thiazolyl sulfoximines exhibited the greatest activity, with LC<sub>50</sub> values as low as 1 ppm.</p> </sec> <sec id="ps3865-sec-0003" sec-type="section"> <title>CONCLUSIONS</title> <p id="ps3865-para-0003">The novel series of <italic>N</italic>‐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. © 2014 Society of Chemical Industry</p> </sec> </abstract>