Synthesis and fungicidal activity of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines

Zi-long Tang; Zan-wen Xia; Shu-hong Chang; Zhao-xu Wang

doi:10.1016/j.bmcl.2015.05.010

Synthesis and fungicidal activity of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3378-81. doi: 10.1016/j.bmcl.2015.05.010. Epub 2015 May 15.

Authors

Zi-long Tang¹, Zan-wen Xia², Shu-hong Chang², Zhao-xu Wang³

Affiliations

¹ School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China; Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China. Electronic address: zltang67@aliyun.com.
² School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
³ School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China; Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201, China.

PMID: 26071637
DOI: 10.1016/j.bmcl.2015.05.010

Abstract

A class of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines was prepared by reactions of 2-methyl-6-((1,3,4-thiadiazolylamino)methyl)phenols or 4-methyl-2-((1,3,4-thiadiazolylamino)methyl)phenols and 2- or 4-nitrobenzaldehyde in the presence of TMSCl in refluxing toluene. The electron-donating methyl group on the benzene ring played an essential role on the reactivity of the substituted phenols, which was proved by DFT calculation. The fungicidal activity of the resultant products were also preliminarily evaluated, most of which displayed moderate to good fungicidal activity. Especially, compound 6f showed 98.0% activity against Sclerotonia sclerotiorum and Botrytis cinerea at concentration of 25μg/mL.

Keywords: (13,4-Thiadiazolyl)-1,3-benzoxazines; Fungicidal activity; Synthesis; TMSCl.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzoxazines / chemical synthesis*
Benzoxazines / chemistry
Benzoxazines / pharmacology*
Botrytis / drug effects*
Fungicides, Industrial / chemical synthesis
Fungicides, Industrial / chemistry
Fungicides, Industrial / pharmacology
Molecular Structure

Substances

Benzoxazines
Fungicides, Industrial