title: Glucose positions affect the phloem mobility of glucose-fipronil conjugates.
abstract: In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
authors.affiliation: State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, and Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University , Guangzhou, Guangdong 510642, People's Republic of China.
authors.forename: Zhiwei
authors.initials: Z
authors.lastname: Lei
authors.forename: Jie
authors.initials: J
authors.lastname: Wang
authors.forename: Genlin
authors.initials: G
authors.lastname: Mao
authors.forename: Yingjie
authors.initials: Y
authors.lastname: Wen
authors.forename: Yuxin
authors.initials: Y
authors.lastname: Tian
authors.forename: Huawei
authors.initials: H
authors.lastname: Wu
authors.forename: Yufeng
authors.initials: Y
authors.lastname: Li
authors.forename: Hanhong
authors.initials: H
authors.lastname: Xu
mesh_terms: D001692:Biological Transport / Q000187:drug effects; D002367:Ricinus communis / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D005947:Glucose / Q000031:analogs & derivatives* / Q000032:analysis / Q000493:pharmacokinetics; D007306:Insecticides / Q000032:analysis / Q000737:chemistry / Q000493:pharmacokinetics*; D015394:Molecular Structure; D052585:Phloem / Q000737:chemistry / Q000378:metabolism*; D011720:Pyrazoles / Q000032:analysis / Q000737:chemistry* / Q000493:pharmacokinetics; D036226:Seedlings / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*
chemical_list: D007306:Insecticides; D011720:Pyrazoles; D005947:Glucose; C082360:fipronil
keywords: click chemistry; glucose positions; glucosyl conjugates; glycosyl azides; phloem mobility