Synthesis and fungicidal activity of novel ureido-substituted 1,3-benzoxazines

Abstract

Ten novel ureido-substituted 1,3-benzoxazines were synthesized in moderate yields by La(OTf)3-catalyzed reaction of some aldehydes with four ureido-substituted 2-aminomethylphenols which were prepared by a one-pot method. Evaluation of their fungicidal activity revealed that most compounds showed moderate to good activity and one of the ureido-substituted 2-aminomethylphenols showed activity against Rhizoctonia solani and Sclerotonia sclerotiorum comparable to the control compound, chlorothalonil.

Solvent-free synthesis of a formaldehyde-free benzoxazine monomer: study of its curing acceleration effect for commercial benzoxazine

“…When performing the reaction with an aldehyde other than formaldehyde, the main method reported for now involves the reaction between an aminomethylphenol and the aldehyde compound. 18,19,23,[67][68][69] In order to obtain 2-substituted benzoxazines, the most reported method implies that the condensation occurs in two distinct steps. First, the primary amine is condensed with salicylaldehyde to furnish the corresponding imine.…”