Plant Growth Regulators

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Abstract
2-Naphthyloxyacetic acid (BNOA), having a side-chain 2 carbon atoms long, is highly active in stimulating seedless fruit development in tomatoes. In this paper it is shown that progressive lengthening of the side-chain results in a series of compounds of which only those having an even number of carbon atoms in the side-chain are active. This is thought to be due to the fact that the even carbon compounds are broken down by oxidation in the plant to the active BNOA, whereas those with odd numbers of carbon atoms are broken down to the inactive β-naphthol. It is further shown that the introduction of a chlorine atom at position 3 in the naphthalene nucleus prevents this oxidation. When the side-chain exceeds 6 carbon atoms in length there is a rapid falling off in the activity of the active members of the series, which is probably due to the slower penetration of these long molecules into the cell.

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