Environmental Fate and Toxicology of Chlorothalonil

Chapter
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 232)

Abstract

The fungicide chlorothalonil (2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile; CAS 1897-45-6; Fig. 1) was introduced in 1965 by Diamond Shamrock Corp. and was first registered in 1966 for use on turfgrass within the United States. An additional registration was granted 4 years later for use on potatoes, marking it the first approved food crop for application (US EPA 1999). It is formulated as concentrates, powders, and granules, among other registered formulations. Some of the prominent products containing chlorothalonil as the active ingredient include Bravo®, Daconil® and Sweep® (US EPA 1999). These or other chlorothalonil formulations have been applied to crops such as celery, beans, peanuts, and peaches, among others. Within the USA, approximately 34% of the total chlorothalonil applied is used on peanuts, 12% on potatoes and 10% on golf courses (US EPA 1999).

References

  1. Armbrust K (2001) Chlorothalonil and chlorpyrifos degradation products in golf course leachate. Pest Manag Sci 57:797–802CrossRefGoogle Scholar
  2. Bedos C, Rousseau-Djabri MF, Loubet B, Durand B, Flura D, Briand O, Barriuso E (2010) Fungicide volatilization measurements: inverse modeling, role of vapor pressure, and state of foliar residue. Environ Sci Technol 44:2522–2528Google Scholar
  3. Bringolf RB, Cope WG, Eads CB, Lazaro PR (2007) Acute and chronic toxicity of technical-grade pesticides to glochidia and juveniles of freshwater mussels (unionidae). Environ Toxicol Chem 26(10):2086–2093CrossRefGoogle Scholar
  4. CDPR, California department of Pesticide Regulation (2005) Chlorothalonil: risk characterization document for dietary exposure. http://www.cdpr.ca.gov/docs/risk/rcd/chlorothalonil.pdf
  5. Caux PY, Kent RA, Fan GT, Stephenson GL (1996) Environmental fate and effects of chlorothalonil: a Canadian perspective. Crit Rev Environ Sci Tech 26(1):45–93CrossRefGoogle Scholar
  6. Chen SK, Edwards CA, Subler S (2001) Effects of the fungicides benomyl, captan and chlorothalonil on soil microbial activity and nitrogen dynamics in laboratory incubations. Soil Biol Biochem 33:1971–1980CrossRefGoogle Scholar
  7. Carlo-Rojas Z, Bello-Mendoza R, Figueroa MS, Sokolov MY (2004) Chlorothalonil degradation under anaerobic conditions in an agricultural tropical soil. Water Air Soil Pollut 151:397–409CrossRefGoogle Scholar
  8. Davies PE, White RWG (1985) The toxicology and metabolism of chlorothalonil in fish. I. Lethal levels for Salmo gairdneri, Galaxias maculatus, G. truttaceus and G. auratus and the fate of 14C-TCIN in S. gairdneri. Aquat Toxicol 7:93–105CrossRefGoogle Scholar
  9. DeLorenzo ME, Wallace SC, Danese LE, Baird TD (2009) Temperature and salinity effects on the toxicity of common pesticides to the grass shrimp, Palaemonetes pugio. J Environ Sci Health B 44:455–460CrossRefGoogle Scholar
  10. Ernst W, Doe K, Jonah P, Young J, Julien G, Hennigar P (1991) The toxicity of chlorothalonil to aquatic fauna and the impact of its operational use on a pond ecosystem. Arch Environ Contam Toxicol 21:1–9CrossRefGoogle Scholar
  11. Farag AT, Abdel-Zaher Karkour T, El Okazy A (2006) Embryotoxicity of oral administered chlorothalonil in mice. Birth Defect Res B 77:104–109CrossRefGoogle Scholar
  12. Fungicide Resistance Action Committee (2013) FRAC code list 2013: fungicides sorted by mode of actionGoogle Scholar
  13. Fushiwaki Y, Urano K (2001) Adsorption of pesticides and their biodegradation products on clay minerals and soils. J Health Sci 47(4):429–432CrossRefGoogle Scholar
  14. Gallagher EP, Canada AT, Di Giulio RT (1992) The protective role of glutathione in chlorothalonil-induced toxicity to channel catfish. Aquat Toxicol 23:155–168CrossRefGoogle Scholar
  15. Gamble DS, Bruccoleri AG, Lindsay E, Langford AH (2000) Chlorothalonil in a quartz sand soil: speciation and kinetics. Environ Sci Technol 34:120–124CrossRefGoogle Scholar
  16. Habte M, Aziz T, Yuen JE (1992) Residual toxicity of soil-applied chlorothalonil on mycorrhizal symbiosis in Leucaena leucocephala. Plant Soil 140:263–268CrossRefGoogle Scholar
  17. Haith DA, Rossi FS (2003) Risk assessment of pesticide runoff from turf. J Environ Qual 32:447–455CrossRefGoogle Scholar
  18. Kwon JW, Armbrust KL (2006) Degradation of chlorothalonil in irradiated water/sediment systems. J Agric Food Chem 54:3651–3657CrossRefGoogle Scholar
  19. Latteur G, Jansen JP (2002) Effects of 20 fungicides on the infectivity of conidia of the aphid entomopathogenic fungus Erynia neoaphidis. BioControl 47:435–444CrossRefGoogle Scholar
  20. Leistra M, Van Den Berg F (2007) Volatilization of parathion and chlorothalonil from a potato crop simulated by the PEARL model. Environ Sci Technol 41:2243–2248CrossRefGoogle Scholar
  21. Liang B, Li R, Jiang D, Sun J, Qiu J, Zhao Y, Li S, Jiang J (2010) Hydrolytic dechlorination of chlorothalonil by Ochrobactrum sp. CTN-11 isolated from a chlorothalonil-contaminated soil. Curr Microbiol 61:226–233CrossRefGoogle Scholar
  22. Monadjemi S, El Roz M, Richard C, Ter Halle A (2011) Photoreduction of chlorothalonil fungicide on plant leaf models. Environ Sci Technol 45:9582–9589CrossRefGoogle Scholar
  23. Mori T, Fujie K, Kuwatsuka S, Katayama A (1996) Accelerated microbial degradation of chlorothalonil in soils amended with farmyard manure. Soil Sci Plant Nutr 42(2):315–322Google Scholar
  24. Motonaga K, Takagi K, Matumoto S (1996) Biodegradation of chlorothalonil in soil after suppression of degradation. Biol Fertil Soils 23:340–345CrossRefGoogle Scholar
  25. Mozzachio AM, Rusiecki JA, Hoppin JA, Mahajan R, Patel R, Beane-Freeman L, Alavanja MCR (2008) Chlorothalonil exposure and cancer incidence among pesticide applicator participants in the agricultural health study. Environ Res 108:400–403CrossRefGoogle Scholar
  26. Mueller DS, Jeffers SN, Buck JW (2005) Toxicity of fungicides to urediniospores of six rust fungi that occur on ornamental crops. Plant Dis 89:255–261CrossRefGoogle Scholar
  27. Park J-W, Lee S-E, Rhee I-K, Kim J-E (2002) Transformation of the fungicide chlorothalonil by fenton reagent. J Agric Food Chem 50:7570–7575CrossRefGoogle Scholar
  28. Patakioutas G, Albanis TA (2002) Adsorption-desorption studies of alachlor, metolachlor, EPTC, chlorothalonil and pirimiphos-methyl in contrasting soils. Pest Manag Sci 58:352–362CrossRefGoogle Scholar
  29. Penuela GA, Barcelo D (1998) Photodegradation and stability of chlorothalonil in water studied by soild-phase disk extraction followed by gas chromatographic techniques. J Chromatogr A 823:81–90CrossRefGoogle Scholar
  30. Potter TL, Wauchope RD, Culbreath AK (2001) Accumulation and decay of chlorothalonil and selected metabolites in surface soil following foliar application to peanuts. Environ Sci Technol 35:2634–2639CrossRefGoogle Scholar
  31. Putnam RA, Nelson JO, Clark JM (2003) The persistence and degradation of chlorothaonil and chlorpyrifos in a cranberry bog. J Agric Food Chem 51:170–176CrossRefGoogle Scholar
  32. Sakkas VA, Lambropoulou DA, Albanis TA (2002) Study of chlorothalonil photodegradation in natural waters and in the presence of humic substances. Chemosphere 48(9):939–945CrossRefGoogle Scholar
  33. Sapozhnikova Y, Wirth E, Schiff K, Brown J, Fulton M (2007) Antifouling pesticides in the coastal waters of Southern California. Mar Pollut Bull 54:1972–1978CrossRefGoogle Scholar
  34. Sato K, Tanaka H (1987) Degradation and metabolism of a fungicide, 2,4,5,6-tetre-chloroisophthalonitrile (TPN) in soil. Biol Fertil Soils 3:205–209CrossRefGoogle Scholar
  35. Sherrard RM, Murray-Gulde CL, Rodgers JH, Shah YT (2003) Comparative toxicity of chlorothalonil: Ceriodaphnia dubia and Pimephales promelas. Ecotoxicol Environ Saf 56:327–333CrossRefGoogle Scholar
  36. Szalkowski MB, Stallard DE (1977) Effect of pH on the hydrolysis of chlorothalonil. J Agric Food Chem 25(1):208–210CrossRefGoogle Scholar
  37. Tillman RW, Siegel MR, Long JW (1973) Mechanism of action and fate of the fungicide chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) in biological systems. I. Reactions with cells and subcellular components of Saccharomyces pastorianus. Pest Biochem Physiol 3:160–167CrossRefGoogle Scholar
  38. Tomlin CDS (2000) The pesticide manual, 12th edn. The British Crop Protection Council, Surrey, UK, pp 620–621Google Scholar
  39. Ukai T, Itou T, Katayama A (2003) Degradation of chlorothalonil in soils treated repeatedly with chlorothalonil. J Pest Sci 28:208–211CrossRefGoogle Scholar
  40. United States Environmental Protection Agency. Office of Pesticide Programs. Special Review and Reregistration Division., Reregistration eligibility decision: chlorothalonil (1999) US Environmental Protection Agency Office of Pesticide Programs Special Review and Reregistration Division: Washington, D.C.Google Scholar
  41. United States Environmental Protection Agency (2007) Office of Pesticide Programs. Potential risks of labeled chlorothalonil uses to the federally listed California red legged frog. 2007, US Environmental Protection Agency Office of Pesticide Programs Environmental Fate and Effects Division: Washington, D.C.Google Scholar
  42. USGS National Water Quality Assessment Data Warehouse http://web1.er.usgs.gov/NAWQAMapTheme/index.jsp
  43. van der Pas LJT, Matser AM, Boesten JJTI, Leistra M (1999) Behaviour of metamitron and hydroxychlorothalonil in low-humic sandy soils. Pest Sci 55:923–934Google Scholar
  44. Vincent PG, Sisler HD (1968) Mechanism of antifungal action of 2,4,5,6-tetrachloroisophthalonitrile. Physiol Plant 21:1249–1264CrossRefGoogle Scholar
  45. Wallace DF, Hand LH, Oliver RG (2010) The role of indirect photolysis in limiting the persistence of crop protection products in surface waters. Environ Toxicol Chem 29(3):575–581CrossRefGoogle Scholar
  46. Waltz C, Armbrust K, Landry G (2002) Chlorpyrifos and chlorothalonil in golf course leachate. http://www2.gcsaa.org/gcm/2002/sept02/pdfs/09chlorpyrifos.pdf
  47. Wan MT, Rahe JE, Watts RG (1998) A new technique for determining the sublethal toxicity of pesticides to the vesicular-arbuscular mycorrhizal fungus Glomus Intraradices. Environ Toxicol Chem 17(7):1421–1428Google Scholar
  48. Wang H, Xu S, Hu J, Wang X (2009) Effect of potassium dihydrogen phosphate and bovine manure compost on the degradation of chlorothalonil in soil. Soil Sediment Contam 18:195–204CrossRefGoogle Scholar
  49. Wang H, Wang C, Chen F, Wang X (2011) Anaerobic degradation of chlorothalonil in four paddy soils. Ecotoxicol Environ Saf 74:1000–1005CrossRefGoogle Scholar
  50. World Health Organization (1996) International Programme on Chemical Safety. Chlorothalonil. Environmental Health Criteria 183. Geneva, Switzerland. http://www.inchem.org/documents/ehc/ehc/ehc183.htm#SubSectionNumber:9.1.3
  51. Wu L, Liu G, Yates MV, Green RL, Pacheco P, Gan J, Yates SR (2002) Environmental fate of metalaxyl and chlorothalonil applied to a bentgrass putting green under southern California climatic conditions. Pest Manag Sci 58:335–342CrossRefGoogle Scholar
  52. Zhang XH, Zhu YG, Lin AJ, Chen BD, Smith SE, Smith FA (2006) Arbuscular mycorrhizal fungi can alleviate the adverse effects of chlorothalonil on Oryza sativa L. Chemosphere 64:1627–1632CrossRefGoogle Scholar
  53. Zhang Y, Lu J, Wu L, Chang A, Frankenberger WT (2007) Simultaneous removal of chlorothalonil and nitrate by Bacillus cereus strain NS1. Sci Total Environ 382:383–387CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  1. 1.Department of Environmental Toxicology, College of Agricultural & Environmental SciencesUniversity of CaliforniaDavisUSA

Personalised recommendations