Synthesis and insecticidal activity of new amide derivatives of piperine

Abstract

The natural lipophilic amides piperine and piperiline were isolated from Piper nigrum L (Piperaceae). Piperine was hydrolysed into piperic acid (85% yield) which was converted into 16 amides (28±89% yield). The contact toxicity of all synthetic amides, and also that of piperine and piperiline, at the dose 10 mg per insect, was evaluated for the Brazilian economically important insects Ascia monuste orseis Latr, Acanthoscelides obtectus Say, Brevicoryne brassicae L, Protopolybia exigua DeSaus and Cornitermes cumulans Kollar. The results demontrated that the insects have different sensivities to the various amides, with mortality ranging from 0 to 97.5% according to the compound and insect species.

A review of Piper spp. (Piperaceae) phytochemistry, insecticidal activity and mode of action

“…However, later it was determined to be a mechanism distinct from that of the pyrethroids when a CNS preparation from American cockroaches, Periplaneta americana, resistant to pyrethroids were affected by the same doses of pipercide that affected susceptible cockroaches (Miyakado et al 1989) and when isobutyl amides were shown to be more potent than pyrethroids against a resistant (superkdr) strain of house fly (Elliott et al 1986). Isobutyl amides from black pepper and their synthetic derivatives (de Paula et al 2000) and from guinea pepper (Gbewonyo et al 1993) were characterized by structure-activity relationships. Synthetic piperamides, derived from natural piperine and piperiline (Fig.…”

“…1M), showed no clear correlation with structure and activity, although N, N-disubstituted amides (Fig. 1N) were most active against the lepidopteran Ascia monuste orseis (Pieridae) (de Paula et al 2000; Table 2). The results of this study were in contrast to the previous work of Miyakado et al (1985, in de Paulo et al 2000 which showed that N-isobutyl substitution had the highest activity.…”

“…Structure-activity relationships between piperamide structure and insecticidal activity Amide + MDP, short chain, N, N-disubstituted Derived from piperine 1N 0.1-1 ade Paula et al (2000) …”

Larvicidal activity of synthetic tropane alkaloids against Ascia monuste orseis (Lepidoptera: Pieridae)

“…Plants produce a plethora of secondary metabolites that play a role in plant defences, and the search for natural products that can be used either as natural pesticides or as models for the development of novel synthetic molecules has been regarded as a promising strategy . In line with this tendency, our research group has been using natural products as a model for the development of new synthetic compounds as potential herbicides or insecticides …”

Sequestration of prenylated benzoic acid and chromenes by Naupactus bipes (Coleoptera: Curculionidae) feeding on Piper gaudichaudianum (Piperaceae)

“…The two most important genera are Piper and Peperomia with approximately 1,700 and 2,000 species, respectively (Quijano-Abril et al 2006;Wanke et al 2007). In spite of the occurrence of several insecticidal compounds in Piper species including amides and neolignans (Gbewonyo and Garnett 1993;Chauret et al 1996;Paula et al 2000;Miranda et al 2003), several herbivorous insects are adapted to feed on Piperaceae (Figueiredo and Sazima 2000;Vanin et al 2008;Ramos et al 2008).…”