Skip to main content
SpringerLink
Log in

Degradation of the insecticide Hydramethylnon byPhanerochaete chrysosporium

  • Published:
Biodegradation Aims and scope Submit manuscript

Abstract

The decomposition of the amidinohydrazone-type insecticide Hydramethylnon (HMN) by soil fungi has been investigated. A simple spectrophotometric method was developed for the estimation of HMN in soil and fungal culture media. HMN was found to be degraded in soil with a half life of 14 to 25 days.

Degradation of HMN by the lignolytic fungus,Phanerochaete chrysosporium yielded two major breakdown products;p-(trifluoromethyl)-cinnamic acid (TFCA) andp-(trifluoromethyl)-benzoic acid (TFBA). TFCA was converted to TFBA which was subsequently metabolised via themeta-fission pathway. Fluoride release from HMN could not be detected.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Abbreviations

BzDAc:

benzene, dioxane, acetic acid (60: 36: 4)

DCM:

dichloroethane

DNPH:

2,4-dinitro-phenylhydrazine

HMN:

Hydramethylnon

TDAc:

toluene, dioxane, acetic acid (90: 30: 1)

TFCA:

p-(trifluoromethyl)-cinnamic acid

TFBA:

p-(trifluoromethyl)-benzoic acid

TFP:

1,5-bis(trifluoro-p-tolyl)-1,4-pentadien-3-one

VA:

veratryl alcohol

References

  • Ageorges A, Pelter A & Ward RS (1991) Enzyme catalysed oxidation of non-phenolic aromatic compounds. Phytochem. 30: 121–126

    Google Scholar 

  • Aitken MD, Venkatadri R & Irvine RL (1989) Oxidation of phenolic pollutants by a lignin degrading enzyme from the white-rot fungusP. chrysosporium. Water Res. 23: 443–450

    Google Scholar 

  • Aust SD (1990) Degradation of environmental pollutants byP. chrysosporium. Microb. Ecol. 20: 197–209

    Google Scholar 

  • Bumpus JA, Tien M, Wright D & Aust SD (1985) Oxidation of persistent environmental pollutants by a white rot fungus,P. chrysosporium. Science 228: 1434–1436

    Google Scholar 

  • Bumpus JA (1989) Biodegradation of polycyclic aromatic hydrocarbons byP. chrysosporium. Appl. Environ. Microbiol. 55: 154–158

    Google Scholar 

  • Bumpus JA & Aust SD (1987) Biodegradation of DDT [1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane] by the white rot fungusP. chrysosporium. Appl. Environ. Microbiol. 53: 2001–2008

    Google Scholar 

  • —— (1990) Biodegradation of environmental pollutants by the white rot fungusP. chrysosporium: involvement of the lignin degrading system. Bioassays 6: 166–170

    Google Scholar 

  • Bumpus JA & Brock BJ (1988) Biodegradation of crystal violet by the white rot fungusP. chrysosporium. Appl. Environ. Micobiol. 54: 1143–1150

    Google Scholar 

  • Cripps C, Bumpus JA & Aust SD (1990) Biodegradation of azo and heterocyclic dyes byP. chrysosporium. Appl. Environ. Microbiol. 56: 1114–1118

    Google Scholar 

  • Dagley S (1971) Catabolism of aromatic compounds by microorganisms. Adv. Microbiol. Physiol. 6: 1–42

    Google Scholar 

  • Dosoretz CG, Dass SB, Reddey CA & Grethlein HE (1990) Protease-mediated degradation of lignin in liquid cultures ofP. chrysosporium. Appl. Environ. Microbiol. 56: 3429–3434

    Google Scholar 

  • Dosoretz CG & Grethlein HE (1991) Physiological aspects of the regulation of extracellular enzymes ofP. chrysosporium. Appl. Biochem. Biotech. 28: 253–265

    Google Scholar 

  • Eggling L (1983) Lignin — an exceptional biopolymer ... and a rich resource? Trends in Biotech. 1: 123–127

    Google Scholar 

  • Fernado T, Aust SD & Bumpus JA (1989) Effects of culture parameters on DDT [1,1,1-trichloro-2,2-bis(4-chloro-phenyl) ethane] biodegradation byP. chrysosporium. Chemosphere 19: 1387–1398

    Google Scholar 

  • Glenn JK & Gold MH (1983) Decolourization of several polymeric dyes by the lignin-degrading basidiomyceteP. chrysosporium. Appl. Environ. Microbiol. 45: 1741–1747

    Google Scholar 

  • Hardman DJ (1991) Biotransformation of halogenated compound. Critical Reviews in Biotechnol. 11: 1–40

    Google Scholar 

  • Harvey PJ (1986) Recent developments in the understanding of lignin biodegradation. J. Biol. Education 20: 169–174

    Google Scholar 

  • Hollingshaus JG & Little RJ (1984b) Toxicity, penetration and metabolism of AC 217,300 (AMDRO) in the tobacco budworm (Heliothis virescens) by various methods of application. Pest. Biochem. Physiol. 22: 329–336

    Google Scholar 

  • Kennedy DW, Aust SD & Bumpus JA (1990) Comparative biodegradation of alkyl halide insecticides by the white rot fungusP. chrysosporium (BKM-F-1767). Appl. Environ. Microbiol. 56: 2347–2353

    Google Scholar 

  • Kirk T, Schultz E, Connors WJ, Lorenz LF & Zeikus JG (1978) Influence of culture parameters on lignin metabolism byP. chrysosporium. Arch. Microbiol. 177: 277–285

    Google Scholar 

  • Kohler A, Jager A, Willershausen H & Graf H (1988) Extracellular ligninase ofP. chrysosporium Burdsall has no role in the degradation of DDT. Appl. Microbiol. Biotech. 29: 618–620

    Google Scholar 

  • Lamar RT, Glaser JA & Kirk TK (1990a) Fate of pentachlorophenol (PCP) in sterile soils innoculated with the white rot basidiomyceteP. chrysosporium: minerilisation, volatilisation and depletion of PCP. Soil Biol. Biochem. 22: 433–440

    Google Scholar 

  • Lamar RT, Larsen MS & Kirk TK (1990b) Sensitivity to and degradation of pentachlorophenol byPhanerochaete spp. App. Environ. Microbiol. 56: 3519–3526

    Google Scholar 

  • Lovell (1979) Proc. 1979 British Crop Protection Conf. Pests and Diseases, pp 572–582

  • Mallipudi NM, Stout SJ, Lee A & Orloski EJ (1986) Photolysis of Amdro fire ant insecticide active ingredient Hydramethylnon (AC217,300) in distilled water. J. Agric. Food Chem. 34: 1050–1057

    Google Scholar 

  • Momohara I, Matsumoto Y & Ishizu A (1991) Degradation of a quinone-type model compound byP. chrysosporium and its lignin peroxidase. Mokuzia Gakkaishi. 37: 63–68

    Google Scholar 

  • Paszcynski A, Pasti MB, Goszczyski S, Crawford DL & Crawford RL (1991) New approach to improve degradation of recalcitrant azo dyes byStreptomyces spp andP. chrysosporium. Enzyme Microb. Technol. 13: 378–384

    Google Scholar 

  • Pellinen J, Joyce TW & Chang H-M (1988) Dechlorination of high-molecular weight chlorolignin by the white rot fungusP. chrysosporium. TAPPI. 71: 191–194

    Google Scholar 

  • Platt MW, Hader Y & Chet I (1985) The decolourisation of the polymeric dye Poly-blue (polyvinalamine sulfonate anthroquinone) by lignin degrading fungi. Appl. Microbiol. Biotech. 21: 394–396

    Google Scholar 

  • Ryan TP & Bumpus JA (1989) Biodegradation of 2,4,5-trichlorophenoxyacetic acid in liquid culture and in soil by the white rot fungusP. chrysosporium. Appl. Microbiol. Biotech. 31: 302–307

    Google Scholar 

  • Smith MR (1991) The biodegradation of aromatic hydrocarbons by bacteria. Biodegradation 1: 191–206

    Google Scholar 

  • Spurr EB (1991) Wasp control by poison baiting: experimental use of hydramethylnon in canned sardine bait. Proc. 44th NZ Weed and Pest Control Conference 1991, pp 42–46

  • Tien M & Kirk TK (1984) Lignin-degrading enzyme fromP. chrysosporium: purification, characterisation and catalytic properties of a unique H2O2 requiring oxygenase. Proc. Nat. Acad. Sci. USA 81: 2280–2284

    Google Scholar 

  • Vander-Meer RK, Williams DF & Lofgren CS (1982) Degradation of the toxicant AC 217300 in Amdro imported fire ant bait under field conditions. J. Agric. Food Chem. 30: 1045–1048

    Google Scholar 

  • Walker JRL & Bong CL (1981) Metabolism of fluoroacetate by a soilPseudomonas sp andFusarium solani. Soil Biol. Biochem. 13: 231–235

    Google Scholar 

  • Walker JRL & Taylor BG (1983) Metabolism of phloroglucinol byFusarium solani. Arch. Microbiol. 134: 123–126

    Google Scholar 

  • Wayne R, Cardaciotto S, Thomson M, Stockton G, Millen W, Conley J, Davis L, Rajan S, Lopata R, Maniara G, Jones M & Wilson L (1988) Physiochemical properties, stability and minor components of Hydramethylnon. Iyakuhin Kenkyu. 19: 966–983

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dept of Plant & Microbial Sciences, University of Canterbury, Christchurch 1, New Zealand

    Grant A. Abernethy & John R. L. Walker

Authors
  1. Grant A. Abernethy
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. John R. L. Walker
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abernethy, G.A., Walker, J.R.L. Degradation of the insecticide Hydramethylnon byPhanerochaete chrysosporium . Biodegradation 4, 131–139 (1993). https://doi.org/10.1007/BF00702330

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00702330

Key words

Search

Navigation