Abstract

The degradation of various formulations of the racemic mixture and the enantiomers (including mefenoxam) of metalaxyl in typical soils from Germany and Cameroon in controlled incubation experiments was studied. The kinetics of the degradation or transformation was determined by means of reversed phase HPLC, while the enantiomeric ratios were measured by HPLC with a chiral Whelk O1 column. The dynamics of the quantitative changes in microbiological properties induced by the addition of these fungicides at their recommended field rates were determined in the soils during a 120-day incubation experiment. The degradation followed first-order kinetics (R > or = 0.96). Higher metalaxyl acid metabolite concentrations were found in German than in Cameroonian soils. The enantiomers of the fungicide had different degradation rates in both soils, with half-lives ranging from 17 to 38 days. All forms of metalaxyl had lower degradation rates in the Cameroonian soil than in the German soil. The degradation of the R-enantiomer was much faster than the S-enantiomer in the German soil and slower than the S-enantiomer in the Cameroonian soil, suggesting that different microbial populations, which may be using different enzymes, have different degradation preferences. The type of soil significantly influenced the effect of these fungicides on the soil parameters studied. Incorporation of these fungicides resulted in a change in the ecophysiological status of the soil microbial community as expressed by microbial activities. The activity of phosphatases and fl-glucosidase, the mineralization and availability of N and most plant nutrients in soils were stimulated, whereas the activity of dehydrogenase and the availability of NO3-, were generally adversely affected. The soil NH4+, NO3-, and enzymes activities values in general did not correlate with the degradation of metalaxyl in both soils. However, the degradation of formulated and unformulated metalaxyl was positively correlated to the activity of acid phosphatase in the German soil (R, 0.84 and 0.94 respectively) and in the Cameroonian soil (R, 0.97 and 0.96 respectively).

Highlights

  • The phenylamide fungicide, metalaxyl, is a chiral compound, which is marketed in its racemic as well as in its enantiopure R form

  • Our findings show that the degradation of metalaxyl in soil occurs with some chiral preference

  • The rate of degradation of enantiomers and the chiral preference depends on the type of soil and is enzymes mediated of which acid phosphatase may play an important role, especially in the tropical soil

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Summary

Introduction

The phenylamide fungicide, metalaxyl, is a chiral compound (structural formula in Fig. 1), which is marketed in its racemic as well as in its enantiopure R form (trade names, e.g., mefenoxam, ridomil etc.) It is manufactured by Syngeta and is used as a seed treatment for banded or broadcast soil application and as a foliar spray in combination with protectant type fungicides such as copper or folpet. The compound is taken up by roots, leaves, green stems and shoots and transported acropetally within the plant, and inhibits the fungal protein synthesis [1, 2]. It is stable under a broad range of pH, temperature and light [3].

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