New insecticidal amides from petroleum ether extract of dried Piper nigrum L. whole fruits.
The petroleum ether extract of dried ground whole fruits of Piper nigrum L. afforded 20 compounds (1-20) including two new insecticidal amides named as pipnoohine (1), and pipyahyine (2), seven reported for the first time from this plant (12, 13, 15-17, 19, 20), and eleven known compounds (3-11, 14, 18). The structure of 1 has been elucidated as (2E,4E,12Z)-N-(4-methylpentyl)octadeca-2,4,12-trienamide and that of 2 as (2E,4E,11E)-12-(benzo[1,3]dioxol-5-yl)-N-(3-methylbutyl)dodeca-2,4,11-trien-amide through extensive ID-, 2D-NMR spectral studies and chemical reactions. The known compounds have been identified through comparison of their spectral data with those reported in literature. 1 and 2 exhibited toxicity at 35.0 and 30.0 ppm respectively against fourth instar larvae of Aedes aegypti L. by WHO method.
Siddiqui
Bina Shaheen
BS
H.E.J. Research Institute of Chemistry, International Centre for Chemical Sciences, University of Karachi, Karachi-75270, Pakistan. bina@khi.comsats.net.pk
Gulzar
Tahsin
T
Mahmood
Azhar
A
Begum
Sabira
S
Khan
Bushra
B
Afshan
Farhana
F
D000473:Alkanes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000577:Amides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D009033:Culicidae / Q000187:drug effects / Q000502:physiology; D005638:Fruit; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029222:Piper nigrum; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D051381:Rats
D000473:Alkanes; D000577:Amides; D007306:Insecticides; D010936:Plant Extracts; C004544:naphtha