title: Synthesis of a series of monosaccharide-fipronil conjugates and their phloem mobility.
abstract: To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean ( Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose-fipronil and D-fucose-fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Ministry of Education, South China Agricultural University, Guangzhou, Guangdong 510642, People's Republic of China.
authors.forename: Jian-Guo
authors.initials: JG
authors.lastname: Yuan
authors.forename: Han-Xiang
authors.initials: HX
authors.lastname: Wu
authors.forename: Meng-Ling
authors.initials: ML
authors.lastname: Lu
authors.forename: Gao-Peng
authors.initials: GP
authors.lastname: Song
authors.forename: Han-Hong
authors.initials: HH
authors.lastname: Xu
mesh_terms: D000818:Animals; D002367:Ricinus communis; D002851:Chromatography, High Pressure Liquid; D007306:Insecticides / Q000138:chemical synthesis* / Q000494:pharmacology; D007814:Larva; D007928:Lethal Dose 50; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000494:pharmacology; D052585:Phloem / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D036226:Seedlings; D018411:Spodoptera
chemical_list: D007306:Insecticides; D009005:Monosaccharides; D011720:Pyrazoles; C082360:fipronil