benzofurans and methyleugenol

Lycoriella ingenua (Dufour) (Diptera: Sciaridae) and Coboldia fuscipes (Meigen) (Diptera: Scatopsidae) are two of the most economically important insect pests of cultivated mushrooms. The toxicities to the fly larvae of the three phenylpropanoids (methyleugenol, myristicin, and safrole) from aerial parts of Asarum sieboldii Miquel (Aristolochiaceae) were compared with those of the currently available carbamate insecticide benfuracarb. In a contact+fumigant mortality bioassay with L. ingenua and C. fuscipes larvae, methyleugenol (1.46 and 2.33 µg/cm2) was the most toxic compound, followed by safrole (2.03 and 2.59 µg/cm2) and myristicin (3.59 and 4.96 µg/cm2), based on 24-h LC50 values. The phenylpropanoids were less toxic than benfuracarb (LC50, 0.75 and 0.55 µg/cm2). In vapor-phase mortality tests with the larvae, the phenylpropanoids were consistently more toxic in closed versus open containers, indicating that the effect of the compounds was largely a result of vapor action. Global efforts to reduce the level of highly toxic synthetic insecticides in the agricultural environment justify further studies on A. sieboldii plant-derived products as potential fumigants for the control of mushroom fly populations in mushroom houses and mushroom compost.

Topics: Allylbenzene Derivatives; Animals; Asarum; Benzofurans; Benzyl Compounds; beta-Alanine; Dioxolanes; Diptera; Eugenol; Fumigation; Insect Control; Insecticides; Larva; Plant Extracts; Pyrogallol; Safrole; Species Specificity

To study the chemical constituents in the nutmeg (seed of Myristica fragrans).. The chemical constituents were isolated by various column chromatographic methods and structurally elucidated by IR, NMR and MS evidences.. Fifteen compounds were obtained and identified as myristicin (1), methyleugenol (2), safrole (3), 2, 3-dihydro-7-methoxy-2(3, 4-methylenedioxyphenyl)-3-methyl-5-(E) -propenyl-benzofuran (4), dehydrodiisoeugenol (5), 2, 3-dihydro-7-methoxy-2-(3-methoxy-4, 5-methylenedioxyphenyl) -3-methyl-5-(E)-propenyl-benzofuran (6), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3, 4-dimetho- xyphenyl) propane (7), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3, 4, 5-trimethoxyphenyl) propane (8), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3, 4-dimethoxyphenyl) propan-1-ol acetate (9), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3, 4-dimethoxyphenyl) propan-1-ol (10), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3, 4, 5-trimethoxyphenyl) propan-1-ol (11), 5-methoxy-dehydrodiisoeugenol (12), erythro-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(4-hydroxy-3-methoxyphenyl)-propan-1-ol (13), guaiacin (14) and threo-2-(4-allyl-2, 6-dimethoxyphenoxy)-1-(3-methoxy-5-hydroxy-phenyl) propan-1-ol (15).. Compound 15 is a new compound and named myrisisolignan. Compound 7 is isolated from the genus Myristica for the first time.

Topics: Allylbenzene Derivatives; Benzofurans; Benzyl Compounds; Dioxolanes; Eugenol; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Myristica; Pyrogallol; Safrole; Seeds