Photolysis of natural β-triketonic herbicides in water

The fate of four natural β-triketones (leptospermone, isoleptospermone, grandiflorone and flavesone, pKa = 4.0-4.5) in aqueous solution, in the dark and upon simulated solar light irradiation was investigated. In anionic form, β-triketones undergo slow dark oxidation and photolysis with polychromatic quantum yields varying from 1.2 × 10(-4) to 3.7 × 10(-4). Leptospermone and grandiflorone are the most photolabile compounds. In molecular form, β-triketones are rather volatile. Polychromatic quantum yields between 1.2 × 10(-3) and 1.8 × 10(-3) could be measured for leptospermone and grandiflorone. They are 3-5 times higher than for the anionic forms. Photooxidation on the carbon atom bearing the acidic hydrogen atom is the main oxidation reaction, common to all the β-triketones whatever their ionization state. However, leptospermone shows a special photoreactivity. In molecular form, it mainly undergoes photoisomerization. Based on this work, the half-lives of β-triketones in surface waters should be comprised between 7 and 23 days.