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Fenpropathrin
Clinical data
ATC code
  • None
Identifiers
  • [Cyano-(3-phenoxyphenyl)methyl] 2,2,3,3-tetramethylcyclopropane-1-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard ( EPA)
ECHA InfoCard 100.049.514 Edit this at Wikidata
Chemical and physical data
FormulaC22H23NO3
Molar mass349.430 g·mol−1
3D model ( JSmol)
  • CC1(C(C1(C)C)C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C
  • InChI=InChI=1S/C22H23NO3/c1-21(2)19(22(21,3)4)20(24)26-18(14-23)15-9-8-12-17(13-15)25-16-10-6-5-7-11-16/h5-13,18-19H,1-4H3
  • Key:XQUXKZZNEFRCAW-UHFFFAOYSA-N

Fenpropathrin, or fenopropathrin, is a widely used pyrethroid insecticide in agriculture and household. [1] [2] [3] [4] Fenpropathrin is an ingestion and contact synthetic pyrethroid. Its mode of action is similar to other natural ( pyrethrum) and synthetic pyrethroids where in they interfere with the kinetics of voltage gated sodium channels causing paralysis and death of the pest. [5] Fenpropathrin was the first of the light-stable synthetic pyrethroids to be synthesized in 1971, but it was not commercialized until 1980. [6] Like other pyrethroids with an α-cyano group, fenpropathrin also belongs to the termed type II pyrethroids (e.g. cyfluthrin, cyhalothrin, cypermethrin, deltamethrin and esfenvalerate). [7] Type II pyrethroids are a more potent toxicant than type I in depolarizing insect nerves. [8] Application rates of fenpropathrin in agriculture according to US environmental protection agency (EPA) varies by crop but is not to exceed 0.4 lb ai/ acre.

Toxicity

A person developed Parkinson's disease after six months of daily exposure to fenpropathrin, and animal tests subsequently revealed that the compound is a dopaminergic neurotoxin. [4] The patient had a history of eating fenpropathrin-poisoned fish for 6 months. [4] The follow-up Dopaminergic degeneration study was conducted using mice treated with fenpropathrin at 15mg/kg/day for 60 days. [4] It has thus been implicated as an environmental risk factor for Parkinson's disease [4] similar to organochlorines, organophosphates and pyrethroids especially at higher doses. [9] [10] [11] [5] An acute reference dose for chronic dietary exposure for fenpropathrin is set at 0.025/mg/kg/day by US EPA. Fenpropathrin is toxic to bees if they come in contact with them directly similar to other insecticides. [12] Toxicity dissipates with time when deposited on foliage and is <24 hours.

Environmental Fate

Fenpropathrin degrades from soil by two main mechanisms, biodegradation and photochemical degradation of surface deposits. [13] The time of degradation depends on the characteristics of the soils. [7] The half-life of disappearance for fenpropathrin in soils was 11 to 17 days under aerobic conditions and approx >1 yr under anaerobic conditions. The half-life of fenpropathrin on the surface of a sterilized sandy loam was in the range of 3 to 4 days following irradiation with natural sunlight.

Trade Names

Danitol, Meothrin, Tame.

See also

References

  1. ^ Aizawa H (2 December 2012). Metabolic Maps of Pesticides. Elsevier Science. pp. 185–. ISBN  978-0-323-15753-7.
  2. ^ Abou-Donia MB (15 July 1992). Neurotoxicology. CRC Press. pp. 462–. ISBN  978-1-4398-0542-8.
  3. ^ Johansen CA, Mayer DF (1990). Pollinator Protection: A Bee & Pesticide Handbook. Wicwas Press. ISBN  978-1-878075-00-0.
  4. ^ a b c d e Xiong J, Zhang X, Huang J, Chen C, Chen Z, Liu L, et al. (March 2016). "Fenpropathrin, a Widely Used Pesticide, Causes Dopaminergic Degeneration". Molecular Neurobiology. 53 (2): 995–1008. doi: 10.1007/s12035-014-9057-2. PMC  5333774. PMID  25575680.
  5. ^ a b Pfeil R (2014). "Pesticide Residues: Pyrethroids". Encyclopedia of Food Safety. Elsevier. pp. 31–34. doi: 10.1016/B978-0-12-378612-8.00239-0. ISBN  978-0-12-378613-5.
  6. ^ Holan G, Frelin C, Lazdunski M (1985). "Selectivity of action between pyrethroids and combined DDT-pyrethroid insecticides on Na+ influx into mammalian neuroblastoma". Experientia. 41 (4): 520–522. doi: 10.1007/bf01966180. ISSN  0014-4754. S2CID  11286824.
  7. ^ a b Pesticide residues in food, 1993 : evaluations, 1993. Part II, Toxicology. World Health Organization, International Program on Chemical Safety. Geneva, Switzerland: World Health Organization. 1994. ISBN  92-4-166509-2. OCLC  31097583.{{ cite book}}: CS1 maint: others ( link)
  8. ^ Salgado VL, Irving SN, Miller TA (1983). "The importance of nerve terminal depolarization in pyrethroid poisoning of insects". Pesticide Biochemistry and Physiology. 20 (2): 169–182. doi: 10.1016/0048-3575(83)90021-4.
  9. ^ Nandipati S, Litvan I (September 2016). "Environmental Exposures and Parkinson's Disease". International Journal of Environmental Research and Public Health. 13 (9): 881. doi: 10.3390/ijerph13090881. PMC  5036714. PMID  27598189.
  10. ^ Van Maele-Fabry G, Hoet P, Vilain F, Lison D (October 2012). "Occupational exposure to pesticides and Parkinson's disease: a systematic review and meta-analysis of cohort studies". Environment International. 46: 30–43. doi: 10.1016/j.envint.2012.05.004. PMID  22698719.
  11. ^ Hansen MR, Jørs E, Lander F, Condarco G, Debes F, Bustillos NT, Schlünssen V (2017-01-01). "Neurological Deficits After Long-term Pyrethroid Exposure". Environmental Health Insights. 11: 1178630217700628. doi: 10.1177/1178630217700628. PMC  5398229. PMID  28469448.
  12. ^ Bahreini R, Nasr M, Docherty C, de Herdt O, Muirhead S, Feindel D (December 2020). "Evaluation of potential miticide toxicity to Varroa destructor and honey bees, Apis mellifera, under laboratory conditions". Scientific Reports. 10 (1): 21529. Bibcode: 2020NatSR..1021529B. doi: 10.1038/s41598-020-78561-2. PMC  7726572. PMID  33299084.
  13. ^ "864. Fenpropathrin (Pesticide residues in food: 1993 evaluations Part II Toxicology)". www.inchem.org. Retrieved 2021-04-09.
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