氟虫腈衍生物-糖基偶合物的合成及其在蓖麻韧皮部的输导性研究

Study on the synthesis of the carbohydrate conjugates of fipronil and their phloem mobility in Ricinus communis

摘要: 为提高氟虫腈在植物体内的输导性,利用葡萄糖、半乳糖与木糖作为导向基团对其进行了糖基化修饰,设计合成了3个含乙酰保护基的糖基-氟虫腈偶合物(a,b,c)和3个脱保护基的偶合物(d,e,f)。采用液相色谱法测定了其在蓖麻幼苗韧皮部中的输导积累性。结果表明:化合物a、b、c无韧皮部输导性,而d、e、f 则具有良好的韧皮部输导性;培养2 h后,收集的第3 h内韧皮部液中 d、e、f 的浓度分别为21.45、14.14 和14.82 μ mol/L。饲料拌毒法测定结果表明,与母体化合物氟虫腈(LC50为4.49 μ mol/L)相比,6个偶合物对亚洲玉米螟Ostrinia furnacalis的杀虫活性均有所下降,LC50值在47.54~78.00 μ mol/L之间。

Abstract: In order to further improve the phloem mobility of fipronil,six novel fipronil glucosides were synthesized by conjugation of fipronil with glucose,galactose and xylose.The phloem concentration of compounds(a-f) in Ricinus communis Linn.was determined by HPLC.Results showed that compounds(d,e,f) had good phloem mobility,the concentrations of d,e,f collected in third hour were 21.45,14.14 and 14.82 μ mol/L,respectively.The bioassays of fipronil and compounds(a-f) against Ostrinia furnacalis were conducted.Compared with fipronil(LC50 value was 4.49 μ mol/L),compounds(a-f) showed lower insecticidal activity against Ostrinia furnacalis (LC50 value between 47.54-78.00 μ mol/L).