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The ability to visualize the movement of glycosyl insecticides contributes to learning their translocation and distribution in plants. In our present work, a novel fluorescent glucose-fipronil conjugate N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino]-2-deoxy-β-D-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (2-NBDGTF), was obtained via click chemistry. Disk uptake experiments showed that an active carrier-mediated system was involved in the 2-NBDGTF uptake process. Meanwhile, 2-NBDGTF exhibited comparable phloem mobility with GTF in castor bean seedlings. Visualization of 2-NBDGTF uptake and transport experiment showed that this fluorescent glucose-fipronil conjugate could be loaded into sieve tubes after transiting through epidermal cells and mesophyll cells and then translocate from cotyledon to hypocotyl via phloem in castor bean seedlings. The results above determined that it is a promising fluorescence tagging approach for revealing the activities of glycosyl insecticides and 2-NBDGTF is a reasonable and feasible fluorescent surrogate of GTF for tracing the distribution of glucose-fipronil conjugates.

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.

Phloem mobility is an important factor for long-distance transport of systemic pesticides in plants. Our previous study revealed that a fluorescent glucose-insecticide conjugate, N-{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-iodo-1H-pyrazol-5-yl}-N-{[1-(β-D-glucopyranosyl)-1H-1,2,3-triazole-4-yl]methyl}-N-{[1-((N-(7-nitrobenz-2-oxa-1,3-diazole-4-amine))-propyl)-1H-1,2,3-triazole-4-yl]methyl}amine (IPGN), can be transported in tobacco cells. Several studies have also indicated that glucose moieties can guide the conjugates into plant cells. In this study, we investigated the phloem mobility of IPGN within castor bean seedlings. Cotyledon uptake experiment results show that IPGN could enter the phloem of the mid-veins of cotyledons. The results of further quantitative analysis show that IPGN was present in small amounts in the phloem sap despite the inconsistencies of physicochemical properties with diffusion through the plasma membrane. Its concentration in the phloem sap (about 370nM at 5h) was much lower than that in the incubation medium (100μM), which suggests that IPGN exhibited weak phloem mobility. After the leaves of Ricinus plantlets were treated with IPGN, green fluorescence could be observed in the phloem of the petioles, bud apical nodes, bud mid-veins, and mid-veins of the untreated leaves. The localization of the fluorescent conjugate at various levels of Ricinus plantlets indicates that it was translocated at a distance to sink organs via sieve tubes. The results proved that introducing a glucose group is a feasible approach to modify non-phloem-mobile pesticides and produce phloem-mobile pesticides., (Copyright © 2014 Elsevier B.V. All rights reserved.)