Insecticidal joint action of pipercide and co-occurring compounds isolated from Piper nigrum L.

Miyakado, Masakazu; Nakayama, Isamu; Yoshioka, Hirosuke

doi:10.1271/bbb1961.44.1701

Cited by 23 publications

(27 citation statements)

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“…It is not as potent as topical applications of α-T, carbaryl, or permethrin, which had 3-day LD 50 s of 599, 42, and 0.8 ng/insect, respectively (Helson et al 1996). However, the activity of the synthesized amides was similar to values obtained by Miyakado et al (1979Miyakado et al ( , 1980 and Gbewonyo (0) 0b (0) 0b (0) Note: The instars for each species were as follows: 2nd, 4th, and 5th for L. dispar, M. disstria, and C. fumiferana, respectively. The final observation period refers to the time when all foliage was consumed by the larvae.…”

Section: Discussionsupporting

confidence: 86%

Efficacy of Piper nigrum (Piperaceae) extract for control of insect defoliators of forest and ornamental trees

et al. 2007

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The acute toxicities of an extract obtained from a plant within the Piperaceae family and related synthetic analogues were tested against four common Canadian forest pest insects. The acute toxicity of the extract from black pepper, Piper nigrum L., was assessed after 1, 24, and 72 h by the percent larval mortality. The 24 h LC 50 estimates for the P. nigrum extract were (in order of decreasing sensitivity) 0.012% for the introduced pine sawfly, Diprion similis (Hartig) (Hymenoptera: Diprionidae), 0.053% for the forest tent caterpillar, Malacosoma disstria Hubner (Lepidoptera: Lasiocampidae), 0.282% for the gypsy moth, Lymantria dispar (L.) (Lepidoptera: Lymantriidae), and 0.998% for the spruce budworm, Choristoneura fumiferana (Clemens) (Lepidoptera: Torticidae). There was no significant increase in mortality after 72 h. Seventy percent of L. dispar larvae dropped off or moved from branches within 1 h of application of 0.2% P. nigrum extract, indicating that these compounds have a repellent effect. Pipercide and nor-pipercide were more toxic to L. dispar and M. disstria larvae than piperolein A and a P. sarmentosum Roxb. amide 72 h after either oral or topical administration of these compounds. Toxic effects of piperamides were more pronounced by oral ingestion. Ninety percent mortality of L. dispar larvae occurred following an oral dose of 5 µg pipercide in diet, whereas mortality was only 40% following topical treatment at 5 µg pipercide/insect. Whole Piper extracts might be useful for the control of sawflies and tent caterpillars in small-scale applications, based on the demonstrated efficacy and reduced risk potential. 522Résumé-Nous avons évalué la toxicité aiguë d'extraits d'une plante de la famille des Piperaceae et d'analogues synthétiques apparentés chez quatre espèces communes d'insectes Can. Entomol. 139: 513-522 (2007) des forêts canadiennes. Nous avons déterminé la toxicité aiguë d'extraits du poivrier noir, Piper nigrum L., après 1, 24 et 72 h d'après le pourcentage de mortalité des larves. Les valeurs estimées de LC 50 après 24 h pour les extraits de P. nigrum sont par ordre de sensibilité décroissante, 0,012 % chez le diprion importé du pin, Diprion similis (Hartig) (Hymenoptera : Diprionidae), 0,053 % chez la livrée des forêts, Malacosoma disstria Hubner (Lepidoptera : Lasiocampidae), 0,282 % chez la spongieuse, Lymantria dispar (L.) (Lepidoptera : Lymantriidae) et 0,998 % chez la tordeuse des bourgeons de l'épinette, Choristoneura fumiferana (Clemens) (Lepidoptera : Tortricidae). Il n'y a pas d'augmentation significative de la mortalité après 72 h. En moins d'une heure après le traitement, 70 % des larves de L. dispar se sont laissées choir ou ont quitté les branches après l'application d'un extrait de 0,2 % de P. nigrum, ce qui indique que ces composés ont un effet répulsif. Soixante-douze h après le traitement, le pipercide et le norpipercide sont plus toxiques pour les larves de L. dispar et de M. disstria que la pipéroléine A et un amide de P. sarmentosum Roxb. lors d'administrations oral...

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Section: Discussionsupporting

confidence: 86%

Efficacy of Piper nigrum (Piperaceae) extract for control of insect defoliators of forest and ornamental trees

et al. 2007

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“…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(Miyakado et al , 1980. P. nigrum seed oil formulations were found to effectively protect stored wheat from both stored grain pests, Sitophilus oryzae (L.) and Rhyzopertha dominica (F.), at concentrations above 100 mg/l for up to 30 days (Sighamony et al 1986).…”

Section: Insecticidal Activitymentioning

confidence: 99%

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

et al. 2007

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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.

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“…Many Piper species have a wide array of natural compounds, which include alkaloids and amides (Scott et al, 2005). It is recorded that Piper nigrum has biological activities such as CNS stimulant, analgaesic, antipyretic and antifeedent activities (Miyakado, Nakayama, & Yoshioka, 1979). Meanwhile, Piper sarmentosum possesses a variety of medicinal properties.…”

Section: Introductionmentioning

confidence: 99%

Alkaloids from Piper sarmentosum and Piper nigrum

Lim

et al. 2009

Natural Product Research

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Detailed chemical studies on the roots of Piper sarmentosum and Piper nigrum have resulted in several alkaloids. The roots of P. sarmentosum gave a new aromatic compound, 1-nitrosoimino-2,4,5-trimethoxybenzene (1). Piper nigrum roots gave pellitorine (2), (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (3), 2,4-tetradecadienoic acid isobutyl amide (4), piperine (5), sylvamide (6), cepharadione A (7), piperolactam D (8) and paprazine (9). Structural elucidation of these compounds was achieved through NMR and MS techniques. Cytotoxic activity screening of the plant extracts indicated some activity.

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Insecticidal joint action of pipercide and co-occurring compounds isolated from Piper nigrum L.

Cited by 23 publications

References 1 publication

Efficacy of Piper nigrum (Piperaceae) extract for control of insect defoliators of forest and ornamental trees

Efficacy of Piper nigrum (Piperaceae) extract for control of insect defoliators of forest and ornamental trees

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

Alkaloids from Piper sarmentosum and Piper nigrum

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