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.

Systemicity is a desirable property for insecticides. Many phytochemicals show good systemic properties and thus are natural sources of novel systemic insecticidal ingredients. Bruceine D, a quassinoid, was identified in Brucea javanica (L.) Merr. and displayed outstanding systemic properties and excellent antifeedant activity against the diamondback moth (DBM, Plutella xylostella L.), beet armyworm (Spodoptera exigua Hübner), and cotton leafworm (Spodoptera litura Fabricius). Its antifeedant effect on third instar larvae of DBM was approximately 6.2-fold stronger than that of azadirachtin. When bruceine D was applied to roots at a concentration of 100 μg/mL for 24 and 48 h, its concentration in flowering Chinese cabbage (Brassica campestris L. ssp. chinensis var. utiliz Tsen et Lee) leaves was 38.69 μg/g (fresh weight, FW) and 108.45 μg/g (FW), respectively. These concentrations could achieve 93.80% and 96.83% antifeedant effects, which were significantly greater than those of azadirachtin. Similar to azadirachtin, bruceine D also posed a potent growth inhibition effect on insect larvae. After feeding with 20 μg/g bruceine D, no pupae were observed. The results demonstrated that bruceine D is an effective botanical insect antifeedant with outstanding systemic properties, causing potent pest growth inhibitory activity.

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.

Enhancing the systemic distribution of a bioactive compound by exploiting the vascular transport system of a plant presents a means of reducing both the volume and frequency of pesticide/fungicide application. The foliar uptake of the glucose-fipronil conjugate N-[3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazol-5-yl]-1-(β-d-glucopyranosyl)-1H-1,2,3-triazole-4-methanamine (GTF) achieved in castor bean (Ricinus communis) and its transport via the phloem are known to be mediated by monosaccharide transporter(s) [MST(s)], although neither the identity of the key MST(s) involved nor the mechanistic basis of its movement have yet to be described. On the basis of homology with Arabidopsis thaliana sugar transporters, the castor bean genome was concluded to harbor 53 genes encoding a sugar transporter, falling into the eight previously defined subfamilies INT, PMT, VGT, STP, ERD6, pGlucT, TMT, and SUT. Transcriptional profiling identified the product of RcSTP1 as a candidate for mediating GTF uptake, because this gene was induced by exposure of the plant to GTF. When RcSTP1 was transiently expressed in onion epidermis cells, the site of RcSTP1 deposition was shown to be the plasma membrane. A functional analysis based on RcSTP1 expression in Xenopus laevis oocytes demonstrated that its product has a high affinity for GTF. The long-distance root-to-shoot transport of GTF was enhanced in a transgenic soybean chimera constitutively expressing RcSTP1.

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