Synthesis and molluscicidal activity of new derivatives of 1-(hydroxy/substituted phenyl)-3-arylpropenones.

Abstract

Several 1-(hydroxy/substituted phenyl)propenones were tested as molluscicidal agents among which the 1-(2-hydroxy/substituted phenyl)-3-(2-furyl)propenones 1a-c show the most promising results. In an attempt to improve their activity, new dihydropyrazolo[1,5-c][1,3]benzoxazines, their thio and their dehydrogenated derivatives were prepared. The pyrazolo[1,5-c][1,3]benzoxazines 4a,b were hydrolyzed affording the 3-(2-furyl)-5-(2-hydroxy/substituted phenyl) pyrazoles 8a,b. The hydroxyimino derivatives 10a-c were synthesized together with their corresponding isoxazole derivatives 11a-c. -Molluscicidal assay indicated that the oximes 10b,c, the isoxazole 11b, the pyrazole 8b, and its N-carbamoyl derivative 9b are most effective. They have in common the conjugated system shown in Fig. 1 which is presumably the active core.