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A. Newman and P. J. S. Pauwels, Tetrahedron 2£, 4605 (1969) Synthesis and Plant Growth Regulator Properties of C-oCarboxyphenyl Derivatives of Five and Six Membered Heterocycles R. L. N. HARRIS, J. L. HUPP ATZ, J. N. PHILLIPS AND T. TEITEI CSIRO, Division of Plant Industry, Canberra, Australia. Abstract - Compounds related to the auxin transport inhibitor l-(2,carboxyphenyl)3-phenylpropan-l,3-dione, in which the 3-diketone moiety has been replaced by five and six membered heterocyclic systems, are discussed.
Lppm, the root elongation of rice was still inhibited to some extent, while the root of radishes considerably elongated. From these results, it seems that the isocoumarins, which have carboxyl (or carboethoxyl)-group at 4-position, have strong phytotoxic activity. 48, 6, 10 and 24 stimulated markedly the seedling growth of radishes. On the whole, radish was more susceptible to these isocoumarins than rice. Only few compounds, No. 41 and 43 were more effective on rice than on radishes. niger. The chemical to be tested was usually dissolved in a small amount of acetone and an aliquot of the solution was spotted on a filter paper of 6 mm in diameter.
The same compound (IX) can however be obtained in 82% yield using an amide-acid chloride adduct type synthesis by the condensation of Η,Ν-dimethylbenzamide with 3-amino-(2,-methyl)cinnamamide in the presence of phosphorus oxychloride. Dichromate oxidation followed by catalytic reduction gave the desired carboxylic acid (X). The pyrimidine analogue (XI) was synthesized in an overall yield of 20% by bromination of 2'-methyl chalcone followed by condensation with urea under acidic conditions and phosphorus oxychloride treatment of the resulting pyrimidone.