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Bioorg Med Chem ; 21(4): 940-7, 2013 Feb 15.
Article in English | MEDLINE | ID: mdl-23321014

ABSTRACT

Twenty 3,5-disubstituted isoxazoles have been synthesized and tested against fourth instar Aedes aegypti larvae. In the synthesis of title compounds, modifications have been made in the C-5 side-chain with a view to test their larvicidal activity. These isoxazoles have been obtained by 1,3-dipolar cycloaddition of arylnitrile oxides to terminal alkynes which furnished the desired products in 20% to 79% yields. A comparative study of the larvicidal activity between 3-(3-aryl-isoxazol-5-yl)-propan-1-ols and 3-(3-aryl-isoxazol-5-yl)-propionic acids clearly demonstrated that the latter compounds possess much better larvicidal activity than the former. We also tested two esters, viz., methyl 3-[3-(phenyl)-isoxazole-5-yl] propionate and methyl 3-[3-(4-chlorophenyl)-isoxazole-5-yl] propionate, where the latter presented an excellent larvicidal profile.


Subject(s)
Aedes/drug effects , Insecticides/chemical synthesis , Isoxazoles/chemistry , Aedes/growth & development , Animals , Insecticides/chemistry , Insecticides/toxicity , Isoxazoles/chemical synthesis , Isoxazoles/toxicity , Larva/drug effects , Structure-Activity Relationship
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