Methyl-1, 5-naphthyridines (I-III) and methyl-1, 6-naphthyridines (IV--VI) were synthesized by the application of crotonaldehyde, methacrolein, or methyl vinyl ketone to 3- and 4-aminopyridines by method a, in the presence of sulfo-mix, ferrous sulfate, and boric acid. 3-Chloro-(VII), 3-bromo-(VIII), and 2, 4-dimethyl-1, 8-naphthyridines (X) were synthesized by the application of glycerol to 5-chloro-, 5-bromo-, and 4, 6-dimethyl-2-aminopyridines by method b, in the presence of sodium m-nitrobenzenesulfonate, ferrous sulfate, and boric acid. The method a was also applied to 4-methyl-, 5-methyl-, 6-methyl-, and 4, 6-dimethyl-2-aminopyridine, and dimethyl- (XI-XVI) and trimethyl-1, 8-naphthyridines (XVII-XIX) were obtained in a high yield. Herbicidal tests on I, III, IV, XI, XIV, XVI, XVIII, XIX, and 1, 5-naphthyridine showed that XI, XIV, XVI, and XVIII possessed a strong herbicidal effect.
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