title: Facile synthesis and herbicidal evaluation of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with 2-phenoxymethyl substituents.
abstract: Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Zumuretiguli
authors.initials: Z
authors.lastname: Aibibuli
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Wang
authors.forename: Haiyang
authors.initials: H
authors.lastname: Tu
authors.forename: Xiaoting
authors.initials: X
authors.lastname: Huang
authors.forename: Aidong
authors.initials: A
authors.lastname: Zhang
mesh_terms: D048588:Benzoxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D001665:Binding Sites; D029741:Brassica rapa / Q000187:drug effects / Q000254:growth & development; D060326:Chemistry Techniques, Synthetic; D003198:Computer Simulation; D031747:Echinochloa / Q000187:drug effects / Q000254:growth & development; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D008958:Models, Molecular; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000494:pharmacology; D010940:Plant Proteins / Q000737:chemistry; D018517:Plant Roots / Q000187:drug effects / Q000254:growth & development; D018547:Plant Stems / Q000187:drug effects / Q000254:growth & development; D011485:Protein Binding; D052999:Quinazolinones / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D048588:Benzoxazines; D006540:Herbicides; D010647:Phenyl Ethers; D010940:Plant Proteins; D052999:Quinazolinones