Abstract
The synthesis of isochroman derivatives 4–9 from α-hydroxylactone 3 is reported. These heterocycles, carrying different substituents on C-3, C-4, and C-8, exhibited different degrees of inhibition of the vegetative growth of wheat (Triticum aestivum cv Klein Escorpion) plants, whereas plant developmental patterns such as their protein profile, carotenes/chlorophylls ratio, and weight/length relationship were not significantly affected. Microscopic observation of transverse sections of shoots and roots showed morphological changes in the treated plants, consistent with delayed development. The results suggest that among these isochromans the C-3 carbonyl moiety of the lactone and the C-4 free hydroxyl group are important but not essential for activity, and that a short side chain appended to C-3 is tolerated. However, cleavage of the C-8 methyl ether group to the related free phenol causes a drastic reduction in the growth inhibitory activity.
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