Design, synthesis and herbicidal activity of novel quinazoline-2,4-diones as 4-hydroxyphenylpyruvate dioxygenase inhibitors

Abstract

The present work indicated that the triketone-containing quinazoline-2,4-dione motif could be a potential lead structure for further development of novel herbicides.

Novel HPPD inhibitors: triketone 2H‐benzo[b][1,4]oxazin‐3(4H)‐one analogs

“…(The crystal structures have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 1450978 and CCDC 1450980.) To synthesize the enol ester ( J ), the acid ( I ) is generally transformed into the corresponding acid chloride using SOCl 2 or ClCOCOCl . The limitation of this method is that it can only be utilized to prepare acid chlorides that are stable and not sensitive to SOCl 2 , ClCOCOCl or heat.…”

“…Modification of the benzene ring of existing triketone HPPD herbicides has been an effective method of obtaining new HPPD inhibitors. Modified benzene rings of these novel HPPD herbicides include: benzo[ d ]oxazol‐2(3 H )‐one, 2,3‐dihydrobenzo[ b ]thiophene‐1,1‐dioxide, 4 H ‐thiochromene, quinoline, aryloxymethylene and quinazoline‐2,4(1 H ,3 H )‐dione …”

“…Modified benzene rings of these novel HPPD herbicides include: benzo[d]oxazol-2(3H)-one, 12 2,3-dihydrobenzo[b]thiophene-1,1-dioxide, 13 4H-thiochromene, 14 quinoline, 8 aryloxymethylene 15 and quinazoline-2,4(1H,3H)dione. 16,17 In our previous work, a series of 2H-1,4-benzoxazin-3-(4H)-one herbicides were designed and synthesized as PPO herbicides. Most of these exhibited excellent herbicidal activity.…”

Synthesis and herbicidal activity of novel pyrazole aromatic ketone analogs as HPPD inhibitor

“…Among them, triketone HPPD herbicides with triketone and aromatic moieties are the most widely studied . For example, many studies have reported that the modification of the aromatic part of triketone derivatives is an effective way to obtain new inhibitors with improved potency. All the modified triketone derivatives mainly focused on aromatic component, which is replaced by heterocycles, aliphatic side chains, fused heterocycles and fused aromatics …”

Design, synthesis, antiviral bioactivity and three‐dimensional quantitative structure–activity relationship study of novel ferulic acid ester derivatives containing quinazoline moiety

“…Quinazoline is an important nitrogenous heterocyclic compound because of its antiviral, antibacterial and herbicidal activities . Previous studies have demonstrated quinazoline derivatives as potential medicinal drugs, and some of them have been used in clinical settings .…”