Effects of Substituents on the Aromatic Ring of Lignano-9,9'-lactone on Plant Growth Inhibitory Activity.

The relationship between the structure of lignano-9,9'-lactone (2,3-dibenzylbutyrolactone) and its activity as a plant growth regulator has been clarified. Derivatives with higher plant growth inhibitory activity than natural dimethylmatairesinol 4 were synthesized. The 2-hydroxy-7- Z-ene derivative 42 displayed growth inhibitory activity against both the shoots (IC50 = 0.65 mM) and roots (IC50 = 0.43 mM) of lettuce seedlings. Regiospecific activity was observed. The 2,3-dihydroxy derivative 24 showed the highest growth inhibitory activity against both the shoots (IC50 = 0.36 mM) and roots (IC50 = 0.13 mM) of Italian ryegrass seedlings. A similar level of activity to 24 against just the roots of Italian ryegrass seedlings was maintained when the hydroxy group at position 3 of the 2,3-dihydroxy derivative 24 was replaced by a fluorine atom. The (2-hydroxy,4-fluoro)-derivative 33 also showed growth inhibitory activity against both the shoots (IC50 = 0.79 mM) and roots (IC50 = 0.14 mM) of Italian ryegrass seedlings. The level of activity was found to depend on the positions of the two hydroxy groups or the hydroxy group and fluorine atom on the aromatic ring. The importance of the lignano-9,9'-lactone structure was also shown.