Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-<i>b</i>]pyridines, a novel class of acyl-ACP thioesterase inhibitors
Jens Frackenpohl, David M. Barber, Guido Bojack, Birgit Bollenbach‐Wahl, Ralf J. Braun, Rahel Getachew, Sabine Hohmann, Kwang‐Yoon Ko, Karoline Kurowski, Bernd Laber, Rebecca L. Mattison, Thomas Müller, Anna M. Reingruber, Dirk Schmutzler, Andrea Svejda
Abstract
The present work covers novel herbicidal lead structures that contain a 2,3-dihydro[1,3]thiazolo[4,5- b ]pyridine scaffold as structural key feature carrying a substituted phenyl side chain. These new compounds show good acyl-ACP thioesterase inhibition in line with strong herbicidal activity against commercially important weeds in broadacre crops, e.g., wheat and corn. The desired substituted 2,3-dihydro[1,3]thiazolo[4,5- b ]pyridines were prepared via an optimized BH 3 -mediated reduction involving tris(pentafluorophenyl)borane as a strong Lewis acid. Remarkably, greenhouse trials showed that some of the target compounds outlined herein display promising control of grass weed species in preemergence application, combined with a dose response window that enables partial selectivity in certain crops.