Fungicidal Properties of Some Novel Trifluoromethylphenyl Amides
Abstract
Trifluoromethylphenyl amides (TFMPAs) were designed and synthesized as potential pesticides. Thirty‐three structures were evaluated for fungicidal activity against three Colletotrichum species using direct bioautography assays. Active compounds were subsequently tested against C. fragariae, C. gloeosporioides, C. acutatum, Phomopsis obscurans, P. viticola, Botrytis cinerea and Fusarium oxysporum. The study identified 2‐chloro‐N‐[2,6‐dichloro‐4‐(trifluoromethyl)phenyl]acetamide (7a) as showing the strongest antifungal activity, and the broadest activity spectrum in this set against Colletotrichum acutatum (at 48 and 72 h) and Phomopsis viticola (at 144 h). The presence of triethylamine in its complex with N‐[2,6‐dichloro‐4‐(trifluoromethyl)phenyl]‐2,2,3,3,3‐pentafluoropropanamide (7b′) played an important role in the bioactivity, and depending on the concentration or fungal species it showed higher or lower activity than the parent amide. X‐Ray crystallography has shown that the complex (7b′) is an ion pair, (C10H2Cl2F8NO)− (C6H16N)+, where a proton is transferred from the amide nitrogen to the triethylamine nitrogen and then connected by hydrogen bonding to the acyl oxygen (N−H 0.893 Å; H⋅⋅⋅O 1.850 Å; N⋅⋅⋅O 2.711 Å; N−H⋅⋅⋅O 161.2(13)°). Although none of these compounds were better than standards, this work revealed some potential lead structures for further development of active novel compounds.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Apr 25, 2019
- Source ID
- 10.1002/cbdv.201800618
Entities
People
- David E. Wedge
- Kenneth J. Linthicum
- Khalil A. Abboud
- Maia Tsikolia
- Nurhayat Tabanca
- Ulrich R. Bernier
Organizations
- Chapman Field
- United States Department of Defense
- University of Florida
- University of Mississippi