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Degradation of carbendazim by UV/H2O2 investigated by kinetic modelling

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Abstract

The transformation of the fungicide carbendazim (methyl-2 benzimidazole carbamate) induced by hydroxyl radical generated by the UV photolysis of H2O2 has been studied in dilute aqueous solution. The efficient reaction of hydroxyl radicals with carbendazim led to the rapid degradation of carbendazim. The study of reaction kinetics yielded a second order rate constant of 2.2±0.3 109 M−1 s−1 for HO· radicals with carbendazim. This value is in agreement with a high reactivity of HO· radicals with carbendazim. Most degradation products were identified by high performance liquid chromatography mass spectrometry (HPLC-MS). In the presence of hydrogenocarbonate and carbonate ions, hydroxyl radicals were quenched and in turn carbonate radicals CO3 ·− were formed. Carbonate radicals are indeed known to react efficiently with compounds containing electron-rich sites such as nitrogen or sulfur atoms. The use of a kinetic modelling software gave evidence for the occurrence of such reactions with carbendazim. The second order rate constant of carbonate radical with carbendazim was equal to 6±2 106 M−1 s−1.

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References

  • Abdou WM, Mahran MR, Sidky MM, Wamhoff H (1985) Photochemistry of pesticides, 3. Photolysis of methyl 2-benzimidazole carbamate in the presence of singlet oxygen. Chemosphere 14:1343–1353

    Google Scholar 

  • Abdou WM, Mahran MR, Sidky MM, Wamhoff H (1986) Photochemistry of pesticides, 6. Comparative photochemical studies on methyl 2-benzimidazolecarbamate (carbendazim) and methyl (1-nbutylcarbamoyl)-2-benzimidazolecarbamate (benlate) in aqueous hydrochloric solution. Chemosphere 15:1063–1071

    Google Scholar 

  • Buxton GU, Greenstock CL, Helman WP, Ross AB (1988) Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (HO·/ O·) in aqueous solution. J Phys Chem Ref Data 17:513–886

    Google Scholar 

  • Chen SN, Cope VW, Hoffman MZ (1973) Behavior of CO3 radicals generated in the flash photolysis of carbonatoamine complexes of cobalt (III) in aqueous solution. J Phys Chem 77:1111–1117

    Google Scholar 

  • De Laat J, Tace E, Doré M (1994) Degradation of chloroethanes in dilute aqueous solution by H2O2/UV. Water Res 28:2507–2519

    Google Scholar 

  • De Laat J, Berger P, Poinot T, Karpel Vel Leitner N, Doré M (1997) Modelling the oxidation of organic compounds by H2O2/UV. Estimation of kinetic parameters. Ozone Sci Eng 19:395–408

    Google Scholar 

  • Delp CJ (1987) Modern selective fungicides. Wiley, London, pp 233–244

  • Fleeker JR, Lacy HM (1977) Photolysis of methyl 2-benzimidazolecarbamate. J Agric Food Chem 25:51–55

    Google Scholar 

  • Gauthier G, Ayele J, Guibaud G (2000) Détermination des propriétés physico-chimiques du carbendazime et conséquences sur son adsorption en CAP. J Eur Hydrol 31:65–84

    Google Scholar 

  • Huang J, Mabury SA (2000a) A new method for measuring carbonate radical reactivity towards pesticides. Environ Toxicol Chem 19:2181–2188

    Google Scholar 

  • Huang J, Mabury SA (2000b) Steady state concentrations of carbonate radicals in field waters. Environ Toxicol Chem 19:2181–2188

    Google Scholar 

  • Huang J, Mabury SA (2000c) The role of carbonate radical in limiting the persistence of sulfur-containing chemicals in sunlit natural waters. Chemosphere 41:1775–1782

    Google Scholar 

  • Larson RA, Zepp RG (1988) Reactivity of the carbonate radical with aniline derivatives. J Environ Toxicol Chem 7:265–274

    Google Scholar 

  • Mazellier P, Leroy E, Legube B (2002) Photochemical behavior of the fungicide carbendazim in dilute aqueous solution. J Photochem Photobiol A: Chem 153:219–225

    Google Scholar 

  • Mendes P (1993) Gepasi: a software package for modelling the dynamics, steady states and control of biochemical and other systems. Comput Appl Biosci 9:563–571

    Google Scholar 

  • Mendes P (1997) Biochemistry by numbers: simulation of biochemical pathways with Gepasi 3. Trends Biochem Sci 22:361–363

    Google Scholar 

  • Neta P Huie RE, Ross AB (1988) Rate constants for reactions of inorganic radicals in aqueous solution. J Phys Chem Ref Data 17:1065–1079

    Google Scholar 

  • Nicole I, De Laat J, Doré M, Duguet JP, Bonnel C (1990) Utilisation du rayonnement ultraviolet dans le traitement des eaux: mesure du flux photonique par actinométrie chimique au peroxyde d'hydrogène. Water Res 24:157–168

    Google Scholar 

  • Panadès R, Ibarz A, Esplugas S (2000) Photodecomposition of carbendazim in aqueous solutions. Water Res 34:2951–2954

    Google Scholar 

  • Tomlin C (1994) The pesticide manual, 10th edn. British Crop Protection Council, Bracknell, London, p 182.

  • Umschlag T, Herrmann H (1999) The carbonate radical (HCO3 ·/CO3 ·−) as a reactive intermediate in water chemistry: kinetics and modelling. Acta Hydrochim Hydrobiol 27:214–222

    Google Scholar 

  • Watkins DAM (1974) Photolysis of methyl benzimidazol-2-yl carbamate. Chemosphere 5:239–240

    Google Scholar 

Download references

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Correspondence to P. Mazellier.

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P. Mazellier can also be reached at http://labo.univ-poitiers.fr/lcee.

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Mazellier, P., Leroy, É., De Laat, J. et al. Degradation of carbendazim by UV/H2O2 investigated by kinetic modelling. Environ Chem Lett 1, 68–72 (2003). https://doi.org/10.1007/s10311-002-0010-7

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  • DOI: https://doi.org/10.1007/s10311-002-0010-7

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