Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents.docVIP

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Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents.doc

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Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents

Molecules 2012, 17, 3181-3201; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Facile Synthesis and Herbicidal Evaluation of 4H-3,1-Benzoxazin-4-ones and 3H-Quinazolin-4-ones with 2-Phenoxymethyl Substituents Zumuretiguli Aibibuli, Yufeng Wang, Haiyang Tu *, Xiaoting Huang and Aidong Zhang * Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China; E-Mails: zumrat010185@ (Z.A.); wangyufeng1213@126.com (Y.W.); hxtowen@ (X.H.) * Authors to whom correspondence should be addressed; E-Mails: haiytu@ (H.T.); adzhang@ (A.Z.); Tel.: +86-27-6786-7635 (A.Z.); Fax: +86-27-6786-7141 (A.Z.). Received: 18 January 2012; in revised form: 27 February 2012 / Accepted: 1 March 2012 / Published: 14 March 2012 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. Keywords: 4H-3,1-benzoxazin-4-ones; 3H-quinazolin-4-ones; active substructure combination; herbicidal activity; auxinic receptor TIR1 1. Introduc