title: Synthesis and fungicidal activity of novel 2-aryl-3-(1,3,4-thiadiazolyl)-6(8)-methyl-1,3-benzoxazines.
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.
authors.affiliation: 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.
authors.forename: Zi-long
authors.initials: ZL
authors.lastname: Tang
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Zan-wen
authors.initials: ZW
authors.lastname: Xia
authors.affiliation: School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China.
authors.forename: Shu-hong
authors.initials: SH
authors.lastname: Chang
authors.affiliation: 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.
authors.forename: Zhao-xu
authors.initials: ZX
authors.lastname: Wang
mesh_terms: D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure
chemical_list: D048588:Benzoxazines; D005659:Fungicides, Industrial
keywords: (13,4-Thiadiazolyl)-1,3-benzoxazines; Fungicidal activity; Synthesis; TMSCl