Design, synthesis and herbicidal evaluation of novel uracil derivatives containing an isoxazoline moiety

Glyphosate is the most widely used and successful herbicide discovered to date, but its utility is now threatened by the occurrence of several glyphosate-resistant weed species. Saflufenacil is a relatively new herbicide developed by BASF in 2010. It is a highly effective selective herbicide showing excellent control on broadleaf weeds (more than 90 species), significantly superior to other protoporphyrinogen oxidase (PPO) inhibitor herbicides at the level of weeds controlled. It is also effective against glyphosate-resistant Conyza canadensis if used in combination with glyphosate. A series of novel uracil-based PPO inhibitors containing an isoxazoline moiety were designed via the intermediate derivatization method, synthesized using a key saflufenacil raw material as starting material and evaluated for herbicidal activity.

The target compounds were characterized by ¹ H NMR and high-resolution electrospray mass spectra. Bioassays indicated that some title compounds can control efficiently and effectively both broadleaf weeds and grassy weeds at low doses, especially the glyphosate-resistant weeds C. canadensis and Eleusine indica.

This work provides a basis for further studies of 9b for control of a wider range of weeds, particularly for glyphosate-resistant weeds.