Insecticidal toxicities of the isolated constituent of Eucalyptus dives oil and its analogues were bioassayed. 3-Carvomenthenone was isolated by chromatographic techniques and determined by EI-MS, 13C-NMR,1H-NMR, 1H-1H COSY, and HMQC. In the fumigant bioassay against P. interpunctella, cyclohexenone exhibited the strongest insecticidal toxicity (LD50 against larvae and adults, 2.45 and 3.63 μg/cm3), followed by methylcyclohexenone, seudenone, and 3-carvomenthenone. In the structure-activity relationships between 3-carvomenthenone analogues and insecticidal toxicity, the mode of the insecticidal action of 3-carvomenthenone, cyclohexenone, methylcyclohexenone, and seudenone was through the dermal organs of T. castaneum and P. interpunctella. This study indicates that 3-carvomenthenone, cyclohexenone, methylcyclohexenone, and seudenone have potential capacity for the development as safety natural agents to control the stored grain insects.

The purpose of this study was to isolate an active constituent from the essential oil of Eugenia caryophyllata leaves and evaluate its insecticidal activity against Pochazia shantungensis nymphs and adults. According to chromatographic and spectroscopic analyses, the active constituent of E. caryophyllata leaves was identified as eugenol. Based on LC50 values and structural analogues of eugenola gainst the P. shantungensis nymphs and adults, isoeugenol (LC50, 83.29 and 91.03 mg/L) exhibited the highest insecticidal activity, followed by methyl isoeugenol (105.61 and 114.48 mg/L), eugenol (124.44 and 143.24 mg/L), methyl eugenol (126.31 and 143.84 mg/L), and acetyl eugenol (165.11 and 170.06 mg/L). Insecticidal activity against P. shantungensis was dependent on the presence of a functional group in 4-ally-2-methoxyphenol. These results indicate that E. caryophyllata oil and eugenol analogues might be potential alternative synthetic insecticidal agents.