Orange seedlings were cultured in aqueous solutions of 3-tert-butyl-5-chloro-6-methyluracil (terbacil and terbacil-2-14C). Radioactivity was distributed throughout the plant with the largest amount in the roots and the smallest amount in the leaves. Terbacil was metabolized to form 3-tert-butyl-5-chloro-6-hydroxymethyl uracil, which was conjugated to form a beta-glucoside as the conjugate was hydrolyzed by beta-glucosidase. Identification of the metabolite was made by infrared and mass spectrometry after isolation and purification by column and thin layer chromatography. An additional unidentified water-soluble material was accumulated in the plant. 5-chloro-uracil was not detected as a metabolite of terbacil.
The ratio of isomeric epoxides obtained by alkaline hydrogen peroxide oxidation of (*)-carvenone and (*)piperitone has been shown to be thermodynamically controlled. cis-and trans-Cawenone epoxides are of almost equal stability, but the preferential formation of the piperitone epoxide with the two alkyl groups trans (V) has been explained in terms of unfavourable steric interactions in the cis-form.
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