Mode of action of naphthalic anhydride as a safener for the herbicide AC 263222 in maize

J. Davies, J. C. Caseley, O. T.G. Jones, M. Barrett, N. D. Polge

Research output: Contribution to journalArticlepeer-review

10 Scopus citations


In hydroponic experiments, seed-dressing with the herbicide safener 1,8-naphthalic anhydride (NA), significantly enhanced the tolerance of maize, (Zea mays L., cv. Monarque) to the imidazolinone herbicide, AC 263222, (2-[4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl]-5-methylnicotinic acid). Uptake, distribution and metabolism studies where [14C]AC 263222 was applied through the roots of hydroponically grown maize plants showed that NA treatment reduced the translocation of radiolabel from root to shoot tissue and accelerated the degradation of this herbicide to a hydroxylated metabolite. Reductions in the lipophilicity and, therefore, mobility of this compound following hydroxylation may account for NA-induced retention of radiolabel in the root system. Hydroxylation of AC 263222 suggested that NA may stimulate the activity of enzymes involved in oxidative herbicide metabolism, such as the cytochrome P450 mono-oxygenases. In agreement with this theory, the cytochrome P450 inhibitor, 1-aminobenzotriazole (ABT), synergized AC 263222 activity and inhibited its hyroxylation in vivo. NA seed-dressing enhanced the total cytochrome P450 and b5 content of microsomes prepared from etiolated maize shoots. Isolated microsomes catalyzed AC 263222 hydroxylation in vitro. This activity possessed the characteristics of a cytochrome P450 mono-oxygenase, being NADPH-dependent and susceptible to inhibition by ABT. Activity was stimulated four-fold following NA seed treatment. Differential NA enhancement of AC 263222 hydroxylase and the cytochrome P450-dependent cinnamic acid-4-hydroxylase (CA4H) activity, suggested that separate P450 isozymes were responsible for each activity. These results indicate that the protective effects of NA result from enhancement of AC 263222 hydroxylation and concomitant reduction in herbicide translocation. This may be attributed to the stimulation of a microsomal cytochrome P450 system.

Original languageEnglish
Pages (from-to)29-38
Number of pages10
JournalPesticide Science
Issue number1
StatePublished - 1998


  • AC 263222
  • Cytochrome P
  • Herbicide metabolism
  • Herbicide safener
  • Maize (Zea mays)
  • Naphthalic anhydride

ASJC Scopus subject areas

  • Applied Microbiology and Biotechnology


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