Synthesis And Insecticidal Activity Of The Dihydroagarofuran Derivatives

In order to study the relationship between structure and insecticidal activity ofβ-dihydroagarofuran compounds, 1β, 2β, 4α, 6α, 8β, 9α, 12- hepthydroxy -β- dihydroagarofuran polyol was used as starting material,reactioned with Methylsulfonyl chloride to give 4α, 6α-bihydroxy-8α, 9α-epoxy-8β-methylsulfony-2β, 12-ether -β- dihydroagarofuran, then etherified and esterified. Most of the compounds were evaluated on their insecticidal activity,and their structures were elucidated mainly based on NMR, IR and HRMS spectral data.1. CompoundⅡⅡ, eight new ether derivatives( 2.1-2.8 ) and two ester derivatives ( 2.9,2.10 ) were synthesized, and their structures were elucidated mainly based on NMR, IR and HRMS spectral data. The preliminary bioassay results showed that ether analogues exhibited some degree stomach toxicity against the third instar larvae of Mythimna separata at the concentration of 20mg/mL, Ethylester ( 2.9 ) and benzoic ester derivatives ( 2.10 ) had no obvious insecticidal activity.2. Compound 2.11 and its reduction product ( 2.12 ) were synthesized, and their structures were elucidated mainly based on NMR spectral data. The preliminary bioassay results indicated that they had no insecticidal activity.3. The ESI-MS spectra of compoundⅡand eight new ether analogues were analyzed. The results showed that the characteristic ions [M+Na]+,[M+K]+,[M+H]+ peaks could be obtained and determined accurately. The ESI-MS was an effective method for detecting these ether analogues.