Novel and Insecticidal Isobutylamides from Dinosperma erythrococca

Abstract

Through insecticidal bioassay-guided fractionation and isolation, five isobutylamides 1-5 were isolated from n-hexane and EtOAc extracts of the aerial parts of Dinosperma erythrococca (Rutaceae). The structures of compounds 1-5 were established through 1D and 2D NMR. Compounds 1-3 were identified as erythrococcamides A-C and represent two novel classes of isobutylamide. Compounds 4-5 were identified as N-(2-hydroxy-2-methylpropyl)-6-phenyl-2(E), 4(E)-hexadienamide (4)1,2 and N-(2-methylpropyl)-6-phenyl-2(E), 4(E)-hexadienamide (5),1,3 respectively. Compound 1 showed lethal activity against the housefly (Musca domestica) (kill EC50 = 20.2 ppm) and the tobacco budworm (Heliothis virescens) (kill EC50 = 74.2 ppm). Compound 4 showed lethal activity against H. virescens at 500 ppm, while compound 5 showed lethal activity against M. domestica at 500 ppm.

One-pot three-component synthesis of the spiroacenaphthylene derivatives

“…4 Heterocycles containing the pyran ring are important targets in synthetic and medicinal chemistry because this fragment is a key moiety in numerous biologically active compounds and natural products. 5,6 Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties. The spiro functionality has been known for a long time to be present in phytochemicals either in alkaloids, lactones or terpenoids.…”

Synthesis and insecticidal activity of new amide derivatives of piperine

“…The potential of this class of compound as a model for the development of new insecticides has been investigated by several researchers. Although many new amides have been prepared, their insecticidal activity has been evaluated against very few insects 7–17…”

The Rediscovery and Leaf Oil Chemistry ofDinosperma longifoliumT.G. Hartley (Rutaceae)

“…Other amides, but not sulfur-containing, have been isolated from the solvent extracts of the wood, bark and leaves of D. erythrococcum and D. melanophloia. These amides also showed insecticidal activity (12,13).…”