Environmental Fate and Ecotoxicology of Fenpropathrin

  • Emerson Kanawi
  • Robert Budd
  • Ronald S. Tjeerdema
Chapter

Abstract

Fenpropathrin ((RS)-α-cyano-3-phenoxybenzyl-2,2,3,3-tetramethylcyclopropane-1-carboxylate; Fig. 1) is a racemic mixture, broad-spectrum pyrethroid insecticide, and acaricide. Discovered by Sumitomo Chemical Company Ltd., then developed by Valent USA, fenpropathrin was the first of the light-stable pyrethroids to be produced. First synthesized in 1971 and commercialized in 1980 (Davies 1985), the technical product (90 % purity) is formulated as an emulsifiable concentrate (30.9 % active ingredient) and is registered in California as Danitol 2.4 EC Spray and Tame 2.4 EC Spray (CDPR 2012b). It is classified as a type II pyrethroid, characterized by the addition of a cyano group at the benzylic carbon. Such α-cyano pyrethroids have enhanced insecticidal activity because of their affinity for voltage-gated membrane channels (Bailey 2009). Synonymous chemical and common names include: α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethyl-1-cyclopropanecarboxylate; Danitol; Danitrol; Fenpropanate; Herald; Meothrin; Rody; S 3206; SD 41706; WL 41706; XE-938; Fenpropathrine; Kilumal; and Ortho Danitol (Kegley et al. 2012). In this chapter, we will discuss fenpropathrin’s uses, its mechanism of toxic action, physical and chemical properties, environmental fate, and ecotoxicology.

References

  1. Akhtar S, Gilani S, Hasan N (2004) Persistence of chlorpyrifos and fenpropathrin alone and in combination with fertilizers in soil and their effects on soil microbes. Pak J Bot 36:863–870Google Scholar
  2. Al-Makkawy H, Madbouly M (1999) Persistence and accumulation of some organic insecticides in Nile water and fish. Resour Conserv Recy 27:105–115CrossRefGoogle Scholar
  3. Bailey JE (2009) U.S. Environmental Protection Agency, FIFRA Scientific Advisory Panel. Meeting minutes. http://www.epa.gov/scipoly/sap/meetings/2009/june/061609minutes.pdf. Accessed 22 Apr 2012
  4. Bellows TS Jr, Morse JG (1993) Toxicity of pesticides used in citrus to Apbytis melinus DeBach (Hymenoptera: Aphelinidae) and Rbizobius lopbantbae (Blaisd.) (Coleoptera: Coccinellidae). Can Entomol 125:987–994CrossRefGoogle Scholar
  5. Cage SA, Bradberry SM, Meachem S, Vale JA (1998) National Poisons Information Service. http://www.intox.org/databank/documents/chemical/fenprop/ukpid64.htm. Accessed 7 Feb 2012
  6. CDPR (2012a) Pesticide use reporting. Database. http://www.cdpr.ca.gov/docs/pur/purmain.htm. Accessed 27 March 2012
  7. CDPR (2012b) Product label. Database. http://www.cdpr.ca.gov/docs/label/labelque.htm. Accessed 27 March 2012
  8. CDPR (2012c) Surface water monitoring. Database. http://www.cdpr.ca.gov/docs/emon/surfwtr/surfcont.htm. Accessed 27 Aug 2012
  9. Chapman R, Tu C, Harris C, Cole C (1981) Persistence of 5 pyrethroid insecticides in sterile and natural, mineral and organic soil. Bull Environ Contam Toxicol 26:513–519CrossRefGoogle Scholar
  10. Davies JH (1985) The pyrethroids: a historical introduction. In: Leahey JP (ed) The pyrethroid insecticides. Taylor and Francis, London, pp 1–41Google Scholar
  11. Day KE (1991) Effects of dissolved organic carbon on accumulation and acute toxicity offenvalerate, deltamethrin and cyhalothrin to Daphnia magna (Straus). EnvironToxicol Chem 10:91–101Google Scholar
  12. Ding Y, Weston D, You J, Rothert A, Lydy M (2011) Toxicity of sediment-associated pesticides to Chironomus dilutus and Hyalella azteca. Arch Environ Contam Toxicol 61:83–92CrossRefGoogle Scholar
  13. Dureja P (1990) Photodecomposition of pyrethroid insecticide fenpropathrin. Pesticides 1989:31–33Google Scholar
  14. HSDB (2012) Fenpropathrin hazardous substances databank. http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?HSDB. Accessed 12 Feb 2012
  15. Katagi T (1993) Effect of moisture content and UV irradiation on degradation of fenpropathrin on soil surfaces. J Pest Sci 18:333–341CrossRefGoogle Scholar
  16. Kegley SE, Hill BR, Orme S, Choi AH (2012) Pesticide action network pesticide database http://www.pesticideinfo.org. Accessed 25 Feb 2012
  17. Laskowski DA (2002) Physical and chemical properties of pyrethroids. Rev Environ Contam Toxicol 174:49–170CrossRefGoogle Scholar
  18. Mauck W, Mayer F, Holz D (1976) Simazine residue dynamics in small ponds. Bull Environ Contam Toxicol 16:1–8CrossRefGoogle Scholar
  19. McEvoy GK (ed) (2000) American Hospital Formulary Service—Drug information. American Society of Health-System Pharmacists, Bethesda, MD, p 3203Google Scholar
  20. Michaud JP (2002) Relative toxicity of six insecticides to Cycloneda sanguinea and Harmonia axyridis (Coleoptera: Coccinellidae). J Entomol Sci 37:82–93Google Scholar
  21. Michaud JP, Grant AK (2003) IPM-compatibility of foliar insecticides for citrus: indices derived from toxicity to beneficial insects from four orders. J Insect Sci 3:18–29Google Scholar
  22. Mikami N, Baba Y, Katagi T, Miyamoto J (1985) Metabolism of the synthetic pyrethroid fenpropathrin in plants. J Agric Food Chem 33:980–987CrossRefGoogle Scholar
  23. Millet M, Wortham H, Sansui A, Mirabel P (1997) Atmospheric contamination by pesticides: determination in the liquid, gaseous and particulate phases. Environ Sci Pollut Res 4:172–180CrossRefGoogle Scholar
  24. PPDB (2009) The pesticide properties database. http://sitem.herts.ac.uk/aeru/footprint/en/index.htm. Accessed 22 March 2012
  25. Sakata S, Yoshimura J, Nambu K, Mikami N, Yamada H (1990) Degradation and leaching behavior of the pyrethroid insecticide fenpropathrin in soils. J Pest Sci 15:363–373CrossRefGoogle Scholar
  26. Sakata S, Mikami N, Yamada H (1992) Degradation of pyrethroids optical isomers in soils. J Pest Sci 17:169–180CrossRefGoogle Scholar
  27. Solomon K, Giddings J, Maund S (2001) Probabilistic risk assessment of cotton pyrethroids: I. Distributional analyses of laboratory aquatic toxicity data. Environ Toxicol Chem 20:652–659CrossRefGoogle Scholar
  28. Song J, Narahashi T (1996) Modulation of sodium channels of rat cerebellar Purkinje neurons by the pyrethroid tetramethrin. J Pharmacol Exp Ther 277:445–453Google Scholar
  29. Takahashi N, Mikami N, Yamada H, Miyamoto J (1985a) Photodegradation of the pyrethroid insecticide fenpropathrin in water, on soil and on plant foliage. J Pest Sci 16:119–131CrossRefGoogle Scholar
  30. Takahashi N, Mikami N, Yamada H, Miyamoto J (1985b) Hydrolysis of the pyrethroid insecticide fenpropathrin in aqueous media. J Pest Sci 16:113–118CrossRefGoogle Scholar
  31. Theng B (1982) Clay-polymer interactions—Summary and perspectives. Clays Clay Miner 30:1–10CrossRefGoogle Scholar
  32. Tomlin CDS (ed) (1994) The pesticide manual—World compendium, 10th edn. The British Crop Protection Council, Surrey, UK, 446Google Scholar
  33. United States Department of Agriculture (2010) Pesticide data program database. www.ams.usda.gov/science/pdp/. Accessed 12 March 2012
  34. United States Environmental Protection Agency (2007) ECOTOX user guide: ECOTOXicology database system. http:/www.epa.gov/ecotox/. Accessed 12 March 2012
  35. Valent U.S.A. Corporation (2008) TAME® 2.4 EC material safety data sheet. http://www.valent.com/Data/Labels/0033rev7.pdf. Accessed 2 May 2012
  36. Voudrias E, Reinhard M (1986) Abiotic organic-reactions at mineral surfaces. ACS Symposium Series 323:462–486CrossRefGoogle Scholar
  37. Wu W, Xu Y, Schramm K, Kettrup A (1999) Effect of natural dissolved humic material on bioavailability and acute toxicity of fenpropathrin to the grass carp, ctenopharyngodon idellus. Ecotoxicol Environ Saf 42:203–206CrossRefGoogle Scholar
  38. Zalmon F, Bolda M, Phillips P (2008) UC IPM pest management guidelines: strawberry. http://www.ipm.ucdavis.edu/PMG/r734300111.html. Accessed 27 May 2012

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Emerson Kanawi
    • 1
  • Robert Budd
    • 2
  • Ronald S. Tjeerdema
    • 1
  1. 1.Department of Environmental Toxicology, College of Agricultural & Environmental SciencesUniversity of CaliforniaDavisUSA
  2. 2.Department of Pesticide RegulationCalifornia Environmental Protection AgencySacramentoUSA

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