title: Synthesis and herbicidal evaluation of triketone-containing quinazoline-2,4-diones.
abstract: Exploring novel 4-hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) inhibitors is one of the most promising research directions in herbicide discovery. To discover new triketone herbicides with broad-spectrum weed control as well as excellent crop selectivity, a series of (total 52) novel triketone-containing quinazoline-2,4-dione derivatives were synthesized and further bioevaluated. The greenhouse testing indicated that many of the newly synthesized compounds showed better or excellent herbicidal activity against broadleaf and monocotyledonous weeds at the dosages of 37.5-150 g of active ingredient (ai)/ha. The structure and activity relationship in this study indicated that the triketone-containing quinazoline-2,4-dione motif has possessed great impact on herbicide activity and may be used for further optimization. Among the new compounds, III-b and VI-a-VI-d displayed a broader spectrum of weed control than mesotrione. In addition, the compound III-b also demonstrated comparatively superior crop selectivity to mesotrione, thus possessing great potential for weed control in the field.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University , Wuhan, Hubei 430079, People's Republic of China.
authors.forename: Da-Wei
authors.initials: DW
authors.lastname: Wang
authors.forename: Hong-Yan
authors.initials: HY
authors.lastname: Lin
authors.forename: Run-Jie
authors.initials: RJ
authors.lastname: Cao
authors.forename: Sheng-Gang
authors.initials: SG
authors.lastname: Yang
authors.forename: Qiong
authors.initials: Q
authors.lastname: Chen
authors.forename: Ge-Fei
authors.initials: GF
authors.lastname: Hao
authors.forename: Wen-Chao
authors.initials: WC
authors.lastname: Yang
authors.forename: Guang-Fu
authors.initials: GF
authors.lastname: Yang
mesh_terms: D015111:4-Hydroxyphenylpyruvate Dioxygenase / Q000037:antagonists & inhibitors / Q000235:genetics / Q000378:metabolism; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D006540:Herbicides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D010940:Plant Proteins / Q000037:antagonists & inhibitors / Q000235:genetics / Q000378:metabolism; D057685:Plant Weeds / Q000187:drug effects / Q000201:enzymology / Q000235:genetics; D011799:Quinazolines / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D006540:Herbicides; D010940:Plant Proteins; D011799:Quinazolines; D015111:4-Hydroxyphenylpyruvate Dioxygenase
keywords: 4-hydroxyphenylpyruvate dioxygenase; crop selectivity; herbicidal activity; quinazoline-2,4-dione; synthesis