Strigolactones (SLs) are plant hormones that regulate the branching of plants and seed germination stimulants of root parasitic plants. As root parasites are a great threat to agricultural production, the use of SL agonists could be anticipated to provide an efficient method for regulating root parasites as suicidal germination inducers. A series of phenoxyfuranone-type SL mimics, termed debranones, has been reported to show potent bioactivities, including reduction of the tiller number on rice, and stimulation of seed germination in the root parasite To exert both activities, two substituents on the phenyl ring of the molecules were important but at least a substituent at the 2-position must be an electron-withdrawing group. However, little is known about the effect of the properties of the substituents at the 2-position on bioactivities. Here, we found that different substituents at the 2-position give different preferences for bioactivities. Halogenated debranones were more effective than the others and SL agonist GR24 for inhibiting rice tiller but far less effective in the induction of germination. Meanwhile, nitrile and methyl derivatives clearly stimulated the germination of seeds. Although their IC values were 100 times higher than that of GR24 in the receptor competitive binding assay, their physiological activities were approximately 1/10 of GR24. These differences could be due to their uptake in plants and/or their physicochemical stability under our experimental conditions. These findings could support the design of more potent and selective SL agonists that could contribute to solving big agricultural issues.