Background: Several 1,2,4,5-tetraoxanes were synthesised, and their herbicidal activity was tested against weeds and compared with the activity of commercial herbicides glyphosate and imazethapyr.
Results: The compounds were prepared by reacting carbonyl compounds with hydrogen peroxide under acid catalysis, affording 1,1-dihydroperoxides (36-91%) that were further converted into 1,2,4,5-tetraoxanes (10-52%) under similar reaction conditions. All products were evaluated against Sorghum bicolor and Cucumis sativus at 0.0125-1.0 mM, and several tetraoxanes caused >70% inhibition of the growth of roots and aerial parts. The most active products were evaluated against the weeds Sorghum arundinaceum, Euphorbia heterophylla, Brachiaria brizantha and Bidens pilosa. Some compounds were highly effective (>80% inhibition at 1.0 mM) against the weeds, showing activity comparable with that of glyphosate or imazethapyr. One of the tetraoxanes was selective, being inactive against dicotyledonous species while inhibiting the roots and aerial parts of monocotyledonous species by 92.9-97.5%, which is comparable with the effect of glyphosate.
Conclusions: Tetraoxanes constitute a new class of effective herbicides with great potential for commercial development.
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