Novel Galactosyl Moiety-Conjugated Furylchalcones Synthesized Facilely Display Significant Regulatory Effect on Plant Growth.

Abstract

The expansion of weed infestation has increased the demand on new herbicides. A series of novel galactosyl moiety-conjugated furylchalcones was facilely synthesized in which the furyl group (A ring) was combined with the substituted benzene group (B ring), and a galactosyl moiety was introduced. All these galactosyl furylchalcones were predicted to be phloem-mobile. Most of the galactosyl furylchalcones significantly promoted early seedling growth of sorghum and barnyardgrass under dark conditions, but all of them revealed considerable anti-growth ability on illuminated pot plants; especially, 1-(3'-(4″-O-β-d-galactopyranosyl)furyl)-3-(4″-nitrophenyl)-2-en-1-one (B11) had a better herbicidal activity against rapeseed and Chinese amaranth than haloxyfop-R-methyl. The median efficient concentrations (EC50) of compound B11 against cucumber and wheat were 9.55 and 26.97 mg/L, respectively, also showing a stronger suppressing capacity than 2,4-D. Molecular docking with phosphoenolpyruvate carboxylase protein showed a stable binding conformation in which the galactosyl group interacted with LYS363 and GLU369, the furan ring and carbonyl bound with ARG184, and the crosslink of the nitro group with GLU240 formed a salt bridge. The results demonstrate that galactosyl furylchalcones possess the great potential as new herbicides for weed management, and further evaluations on more weeds are required for practical application.