Joint action of benzoxazinone derivatives and phenolic acids

J Agric Food Chem. 2006 Feb 22;54(4):1049-57. doi: 10.1021/jf051156r.

Abstract

The joint action of binary and ternary mixtures of benzoxazinone derivatives and phenolic acids was studied using the additive dose model (ADM) as reference model. The activity of fixed-ratio mixtures of phenolic acids [ferulic acid (FA), p-coumaric acid (CA), vanillic acid (VA), and p-hydroxybenzoic acid (HBA)] and benzoxazinone derivatives [2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), 6-methoxybenzoxazolin-2-one (MBOA), benzoxazolin-2-one (BOA), 2-aminophenol (AP), and N-(2-hydroxyphenyl)acetamide (HPAA)] on Lolium perenne and Myosotis arvensis root growth was assessed in Petri dishes. Root length was recorded 6 days after seeding, and EC(50) and EC(90) values were estimated using nonlinear regression analyses. The benzoxazinone derivatives were found to be more phytotoxic than the phenolic acids, particularly on M. arvensis. Binary mixtures of phenolic acids responded predominantly additively on both plant species. Deviations from additivity were species-specific with antagonistic responses on L. perenne and synergistic responses on M. arvensis. Similarly, binary mixtures of benzoxazinone derivatives also followed the ADM, although synergistic responses were observed for BOA + AP and BOA + HPAA. Binary and ternary mixtures of benzoxazinone derivatives and phenolic acids responded primarily antagonistically; however, a significant synergistic performance was observed with DIMBOA + FA and DIMBOA + VA on L. perenne. These results do not support the assumption that allelopathic effects of wheat can be attributed to synergistic effects of otherwise weakly active allelopathic compounds, and it is suggested that future research be directed toward identifying and studying the effects of other potential allelochemicals including the degradation products of the most abundant wheat allelochemicals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids, Carbocyclic / pharmacology*
  • Benzoxazines
  • Benzoxazoles / pharmacology*
  • Coumaric Acids / pharmacology
  • Drug Synergism
  • Herbicides / pharmacology
  • Lolium / drug effects*
  • Magnoliopsida / drug effects*
  • Oxazines / pharmacology*
  • Parabens / pharmacology
  • Pheromones / pharmacology
  • Propionates
  • Vanillic Acid

Substances

  • Acids, Carbocyclic
  • Benzoxazines
  • Benzoxazoles
  • Coumaric Acids
  • Herbicides
  • Oxazines
  • Parabens
  • Pheromones
  • Propionates
  • benzoxazolone
  • 6-methoxybenzoxazolinone
  • ferulic acid
  • Vanillic Acid
  • p-coumaric acid
  • 4-hydroxybenzoic acid
  • 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one