Synthesis and herbicidal activity of a pentafluorosulfanyl analog of trifluralin

Abstract

The synthesis of 2,6-dinitro-4-pentafluorosulfanyl-N,N-dipropylaniline, 2, was achieved in a straightforward manner from commercially available 1-nitro-4-pentafluorosulfanylbenzene. In postemergence screening 2 was found to be approximately twice as potent as trifluralin with the same general spectrum of activity. In contrast, in pre-emergence tests, 2 was nearly 5 fold more potent against quackgrass and crabgrass. Given the existing structureactivity-relationship for adverse properties of the dinitroaniline herbicides, 2 is proposed to have properties quite comparable to the commercial agent trifluralin.

Pentafluorosulfanyl as a Novel Building Block for Enzyme Inhibitors: Trypanothione Reductase Inhibition and Antiprotozoal Activities of Diarylamines

“…[11][12][13] Fueled by the knowledge of the pronounced influence of fluorine on the physical and chemical properties [14,15] and therefore on the bioactivity of molecules, the interest of the life science industry in novel fluorine containing substituents is nowadays prevalent. Accordingly, the SF 5 group has gained the attraction of crop A C H T U N G T R E N N U N G science in the recent years, as underlined by the growing number of patents [16] and research articles [5,17,18] for mainly agrochemicals containing this functional group.…”

Hemisynthetic trifluralin analogues incorporated in liposomes for the treatment of leishmanial infections

“…Their preclinical development has been hindered by low water solubility and poor pharmacokinetics. Recent research efforts were focused on chemical modification studies [25,[29][30][31] and development of NanoDDS aiming to increase dinitroanilines solubility and improve their activity against parasite [22][23][24]. Our previous work demonstrated the successful development of conventional and long-circulating liposomes containing TFL as the formulations were active against different species of Leishmania infecting both mice and dogs [20,21].…”

Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules

“…Remarkably, the SF 5 -trifluralin demonstrated 5-fold greater herbicidal potency relative to the parent CF 3 -compound. This was rationalised according to a favourable interaction of the SF 5 residue with a key Thr239 residue of -tubulin, which is associated with the electron-rich surface of this group that apparently interacts even more favourably than the CF 3 [108].…”