Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

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 BH3-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.

Beilstein J. Org. Chem. 2024, 20, 540–551. doi:10.3762/bjoc.20.46

Source: Beilstein Journal of Organic Chemistry - March 1, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: 2,3-dihydro[1,3]thiazolo[4,5-b]pyridine acyl-ACP thioesterase bioisostere herbicide heterocycle Full Research Paper Source Type: research