Preparation and phytotoxicity of sorgoleone analogues

3,5-Dimethoxybenzylic alcohol was converted into the 2-acetoxy-5-methoxy-3-(pent-1-yl)-1,4-benzoquinone (12), in seven steps, with an overall yield of 14.6%. The natural quinone sorgoleone (1) was isolated from Sorghum bicolor and converted into the corresponding quinone (13) having a saturated side chain. The selective effects of these compounds (1, 12 and 13), at the dose of 5.6 mug of a.i./ g of substrate, on the growth of Cucumis sativus, Lactuca sativa, Desmodium tortuosum, Hyptis suaveolens and Euphorbia heterophylla were evaluated. All three compounds caused some inhibition on the root growth of the test plants (0.0-69.19%) with the aerial parts less affected. The results showed that the triene unit of the sorgoleone side chain is not essential for the phytotoxicity and also the synthetic quinone was as active as the natural product.