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Synthesis, stability and insecticidal activity of 2-arylstilbenes.

Authors
  • Horty, Lindsey G1
  • Daeuble, John F1
  • Castetter, Scott1
  • Olson, Monica B1
  • Wessels, Frank J1
  • Wang, Nick X1
  • 1 Corteva Agriscience™, Agricultural Division of DowDuPont, Indianapolis, IN, USA. , (India)
Type
Published Article
Journal
Pest Management Science
Publisher
Wiley (John Wiley & Sons)
Publication Date
Nov 01, 2019
Volume
75
Issue
11
Pages
3015–3023
Identifiers
DOI: 10.1002/ps.5416
PMID: 30891871
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

A chemical scaffold-hopping approach from known 3-hydroxyl-3-methylglutaryl-CoA (HMG-CoA) reductase inhibitors identified (E/Z)-2-arylstilbenes as novel insecticidal hits against two lepidopteran species, Spodoptera exigua and Trichoplusia ni. A structure-activity relationship (SAR) study of the aryl substituents and the E/Z conformations was carried out in an effort to improve insecticidal potency. A series of (E/Z)-2-arylstilbenes was prepared and separated to evaluate their insecticidal potency against lepidopterous species in diet-feeding assays. The results showed that the (Z)-2-arylstilbenes were more active than their corresponding (E)-isomers, and a stereoselective synthesis was utilized to expand the SAR of the (Z)-2-arylstilbenes. (Z)-4'-Fluoro-3'-methyl-2-(2,4-difluorostyryl)-4-fluoro-5-methoxy-1,1'-biphenyl was the most potent analog in this study with strong activity against S. exigua, T. ni, Helicoverpa zea, Plutella xylostella and Pseudoplusia includens. The (Z)-2-arylstilbenes were found to have strong insecticidal potency against five lepidopteran species. Ultimately, synthetic efforts could not improve insecticidal potency to commercial levels, and a lack of UV stability led to efforts being discontinued. © 2019 Society of Chemical Industry. © 2019 Society of Chemical Industry.

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