Collect. Czech. Chem. Commun. 1992, 57, 1521-1536

Synthesis and Fungicidal Activity of Isoxazolines Fused to 3,5-Dichloromaleimide

Marta Konopíkováa, Lubor Fišeraa and Naďa Prónayováb

a Department of Organic Chemistry, Slovak Technical University, 812 37 Bratislava
b Central Laboratory of Chemical Techniques, Slovak Technical University, 812 37 Bratislava


3-Phenyl-5-(3,5-dichlorophenyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (III, R = H) and 3-phenyl-5-(3,5-dichlorophenyl)-6a-methyl-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazoles (IV, R = CH3) were prepared by 1,3-dipolar cycloaddition of substituted benzonitrile oxides I to N-(3,5-dichlorophenyl)maleimide (I, R = H), or its methyl derivative II (R = CH3). Cycloaddition to compound II (R = CH3) proceeded regiospecifically. Reduction of IVg with NaBH4 was regio- and stereoselective to yield the hydroxylactams VIIg, VIIIg, and IXg. Antifungal activity of several products was worse than that of commercial preparations.