The Piperaceae Amides I: Structure of Pipercide, A New Insecticidal Amide from Piper nigrum L.
01 Jul 1979-Agricultural and biological chemistry (Japan Society for Bioscience, Biotechnology, and Agrochemistry)-Vol. 43, Iss: 7, pp 1609-1611
TL;DR: The Piperaceae Amides I: Structure of Pipercide, A New Insecticidal Amide from Piper nigrum L. as discussed by the authors, Vol. 43, No. 7, pp. 1609-1611
Abstract: (1979). The Piperaceae Amides I: Structure of Pipercide, A New Insecticidal Amide from Piper nigrum L. Agricultural and Biological Chemistry: Vol. 43, No. 7, pp. 1609-1611.
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TL;DR: The secondary metabolites isolated from Piper species for the period 1907 to June 1996 have been reviewed in this paper, where nearly six hundred chemical constituents belonging to different classes of bioactive compounds are listed together with their source(s) and references.
849 citations
TL;DR: The conclusions of the current work with Piperaceae are that Piper extracts offer a unique and useful source of biopesticide material for controlling small-scale insect out-breaks and reducing the likelihood of resistance development when applied as a synergist with other botanical insecticides such as pyrethrum.
Abstract: The tropical plant family Piperaceae has provided many past and present civilizations with a source of diverse medicines and food grade spice. The secondary plant compounds that produce these desired qualities function also as chemical defenses for many species in the genus Piper. The compounds with the greatest insecticidal activity are the piperamides. Many studies have shown the effectiveness of Piper spp. extracts for the control of stored products pests and recently studies from our laboratory group have tested the extracts of Piper. nigrum, P. guineense and P. tuberculatum against insect pests of the home and garden. These results and those from investigations that examined the biochemical and molecular modes of action of the piperamides singly or in combination will be the focus of this review. The conclusions of our current work with Piperaceae are that Piper extracts offer a unique and useful source of biopesticide material for controlling small-scale insect out-breaks and reducing the likelihood of resistance development when applied as a synergist with other botanical insecticides such as pyrethrum.
236 citations
Cites background from "The Piperaceae Amides I: Structure ..."
...Early investigations with P. nigrum seed extracts indicated that piperamides were responsible for the toxicity of the extracts to the adzuki bean weevil Callosobruchus chinensis L. (Miyakado et al. 1979, 1980)....
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TL;DR: The authors' present society can afford to discuss long-term health implications of agents used to control insect pests, and many new and difficult questions have emerged about health and environmental health, giving rise to a distinct area of study called risk assessment.
Abstract: For centuries humans have used natural insecticides to combat insect pests that compete for our food and fiber or that affect public health. Some of these compounds were plant extracts or plant parts, others were mined from the earth. In the twentieth century synthetic insecticides have replaced natural ones as the standard means of controlling detrimental insects, ticks, and mites. Although early natural insecticides such as arsenicals and nicotine carried with them acknowledged risks, a populace that often faced hunger and vector-borne diseases was willing to tolerate a degree of risk to realize the benefits of the chemicals being used. Synthetic insecticides brought a new order of insect control, but also a new collage of risks. As people became more comfortable in the developed areas of the world, threats of starvation, arthropod-vectored diseases, or loss of clothing and shelter often became minor concerns. The quality of our food supply and the economics of production now govern the majority of pest and pesticide approaches, products, and methodologies. At the same time, new questions have arisen regarding environmental quality, especially contamination of water, air, and soil by a host of chemicals, some of which are pesticides ' or their degradation products. Our present society can afford to discuss long-term health implications of agents used to control insect pests. Many new and difficult questions have emerged about health and environmental nsks, giving rise to a distinct area of study called risk assessment. One of the most challenging questions
190 citations
TL;DR: The results suggest that Piper extracts could be used effectively as contact botanical insect control agents to protect potato plants from developing L. decemlineata larvae and to control insecticide resistant populations in conjunction with other integrated pest management (IPM) strategies used in conventional and organic agriculture.
Abstract: The efficacy of extracts from two Piperaceae species, Piper nigrum L. and P. tuberculatum Jacq. were evaluated using larvae and adults of the Colorado Potato Beetle Leptinotarsa decemlineata (Say). Young larvae and neonates were the most susceptible; a 24-h LD(50) of 0.064% extract of P. tuberculatum was determined for 4-day-old larvae, while 0.05% extract of P. nigrum reduced larval survival up to 70% within one week after treatment of potato Solanum tuberosum L. (Solanaceae) plants. When an insecticide resistant strain of L. decemlineata larvae was tested with the P. tuberculatum extract, there was less than a 2-fold tolerance ratio compared to the 22-fold tolerance ratio to cypermethrin, a pyrethroid. Older larvae, pre-pupal stage and adults, were less sensitive to the P. nigrum extracts; the 24-h LD(50) was 0.5% (95% C.I. = 0.36, 0.65). However, the same concentration was equally effective under field conditions. In the greenhouse, P. nigrum at 0.5% was as effective at reducing adult L. decemlineata feeding as combinations with 2 separate botanical mixtures, garlic and lemon grass oil. Under field conditions, the residual activity of the P. nigrum extracts was less than 3 h. When adult L. decemlineata were placed on treated plants exposed to full sunlight for 0, 1.5, and 3 h, leaf damage progressively increased as the main active compound, piperine, was found to degrade by 80% after 3 h. An in vitro polysubstrate monoxygenase (PSMO) enzyme assay, using the substrate methoxyresorufin O-demethylation (MROD), determined that the principal P. nigrum active compound, piperine, is responsible for inhibition of that specific enzyme. The results suggest that Piper extracts could be used effectively as contact botanical insect control agents to protect potato plants from developing L. decemlineata larvae at concentrations less than 0.1%. There is also potential for Piper extracts to control insecticide resistant populations in conjunction with other integrated pest management (IPM) strategies used in conventional and organic agriculture.
163 citations
Cites background from "The Piperaceae Amides I: Structure ..."
...Early investigations with P. nigrum indicated that amides were responsible for the toxicity of the extracts to the adzuki bean weevil Callosobruchus chinensis L. (Miyakado et al., 1979, 1980)....
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...1C), approximately 100-fold more active than piperine (Miyakado et al., 1979, 1980; Dev and Koul, 1997)....
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TL;DR: Toxicities of two piperidine alkaloids, pipernonaline and piperoctadecalidine, isolated from Piper longum L. were determined against five species of arthropod pests.
120 citations
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