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Biotransformation of benzonitrile herbicides via the nitrile hydratase–amidase pathway in rhodococci

  • Environmental Microbiology
  • Published:
Journal of Industrial Microbiology & Biotechnology

Abstract

The aim of this work was to determine the ability of rhodococci to transform 3,5-dichloro-4-hydroxybenzonitrile (chloroxynil), 3,5-dibromo-4-hydroxybenzonitrile (bromoxynil), 3,5-diiodo-4-hydroxybenzonitrile (ioxynil) and 2,6-dichlorobenzonitrile (dichlobenil); to identify the products and determine their acute toxicities. Rhodococcus erythropolis A4 and Rhodococcus rhodochrous PA-34 converted benzonitrile herbicides into amides, but only the former strain was able to hydrolyze 2,6-dichlorobenzamide into 2,6-dichlorobenzoic acid, and produced also more of the carboxylic acids from the other herbicides compared to strain PA-34. Transformation of nitriles into amides decreased acute toxicities for chloroxynil and dichlobenil, but increased them for bromoxynil and ioxynil. The amides inhibited root growth in Lactuca sativa less than the nitriles but more than the acids. The conversion of the nitrile group may be the first step in the mineralization of benzonitrile herbicides but cannot be itself considered to be a detoxification.

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Abbreviations

NHase:

Nitrile hydratase

L-NHase:

Low molecular weight NHase

H-NHase:

High molecular weight NHase

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Acknowledgments

Financial support via projects OC09046 (Ministry of Education of the Czech Republic), EU project MINOTAURUS (7th FP, project no. 265946), P504/11/0394 and 305/09/H008 (Czech Science Foundation) and the LLP-Erasmus Programme grant to F.P. is gratefully acknowledged.

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Authors and Affiliations

  1. Institute of Microbiology of the Academy of Sciences of the Czech Republic, v.v.i., Vídeňská 1083, 142 20, Prague, Czech Republic

    Alicja B. Veselá, Helena Pelantová, Miroslav Šulc, Martina Pičmanová, Miroslav Pátek & Ludmila Martínková

  2. Faculty of Food and Biochemical Technology, Institute of Chemical Technology Prague, Technická 5, 166 28, Prague, Czech Republic

    Martina Macková, Petra Lovecká & Markéta Thimová

  3. Department of Chemistry, Chemical Engineering and Materials, University of L’Aquila, via Campo di Pile, Zona industriale di Pile, 67 100, L’Aquila, Italy

    Fabrizia Pasquarelli

  4. Department of Biotechnology, Himachal Pradesh University, Summer Hill, Shimla, 171005, Himachal Pradesh, India

    Tek Chand Bhalla

  5. Department of Biochemistry, Charles University, Hlavova 2030, 128 43, Prague, Czech Republic

    Miroslav Šulc

Authors
  1. Alicja B. Veselá
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  2. Helena Pelantová
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  11. Ludmila Martínková
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Correspondence to Ludmila Martínková.

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Veselá, A.B., Pelantová, H., Šulc, M. et al. Biotransformation of benzonitrile herbicides via the nitrile hydratase–amidase pathway in rhodococci. J Ind Microbiol Biotechnol 39, 1811–1819 (2012). https://doi.org/10.1007/s10295-012-1184-z

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  • DOI: https://doi.org/10.1007/s10295-012-1184-z

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