Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX

A series of 10 3 -(hetarylaminomethylene)quinolinediones, 12 3-(substituted aminopropenoyl)-4-hydroxyquinolinones, and 10 3-(substituted aminomethylene-5-oxo-pyrazolinyl)-4-hydroxyquinolinones were synthesized as novel enaminones derived from 3-(un)substituted 4-hydroxyquinolin-2(1H)-ones in 72-94% yields and assayed for their molluscicidal activities against Biomphalaria alexandrina and Lymnaea natalensis snails. Some of the tested enaminones presented high molluscicidal activities (LC50 <= 20 ppm). The new compounds showed more potency against hatchability of B. alexandrina egg masses, the infection rate and prepatent period of the snails. In addition, these derivatives revealed potential larvicidal effects (100% mortality) on both miracidia and cercariae of Schistosoma mansoni at reduced exposure time. The selected active derivatives were examined against Daphnia magna and their nontoxic effect at all sublethal, lethal, and higher concentrations suggests that these compounds can play an important role as molluscicides and larvicides with environmental safe properties. (c) 2005 Elsevier Ltd. All rights reserved.