Phenothrin

Phenothrin
Names
IUPAC name
(3-Phenoxyphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
Other names
Sumithrin; Phenothrine; Phenoxythrin; Sumitrin; Wellcide; Pibutin; Anvil; Duet; Anchimanaito 20S
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.043.079
EC Number 247-404-5
KEGG
MeSH Phenothrin
UNII
Properties
C23H26O3
Molar mass 350.451 g/mol
Melting point <25 °C
Boiling point >290 °C
Pharmacology
P03AC03 (WHO) QP53AC03 (WHO)
Hazards
R-phrases (outdated) R36 R38
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenothrin, also called sumithrin and d-phenothrin,[1] is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans. d-Phenothrin is used as a component of aerosol insecticides for domestic use. Phenothrin is often used with methoprene, an insect growth regulator that interrupts the insect's biological life cycle by killing the eggs. Phenothrin is the active agent in the branded product Raid Fly & Wasp Killer.

Effects

Phenothrin is primarily used to kill fleas and ticks.[2] It is also used to kill head lice in humans, but studies conducted in Paris, France and the United Kingdom have shown widespread resistance to phenothrin.[2]

It is extremely toxic to bees. A U.S. Environmental Protection Agency (EPA) study found that 0.07 micrograms was enough to kill honey bees.[2] It is also extremely toxic to aquatic life with a study showing concentrations of 0.03 ppb killing mysid shrimp.[2] It has increased risk of liver cancer in rats and mice in long term exposure.[2] It is capable of killing mosquitoes,[3] although remains poisonous to cats and dogs, with seizures and deaths being reported due to poisoning.[2] Specific data on concentrations or exposure is lacking.

Phenothrin has been found to possess antiandrogen properties, and was responsible for a small epidemic of gynecomastia via isolated environmental exposure.[4][5]

The EPA has not assessed its effect on cancer in humans. However, one study performed by the Mt. Sinai School of Medicine links sumithrin with breast cancer; the link made by sumithrin's effect on increasing the expression of a gene responsible for mammary tissue proliferation.[2]

EPA action

In 2005, the U.S. EPA canceled permission to use phenothrin in several flea and tick products, at the request of the manufacturer, Hartz Mountain Industries.[6][7] The products were linked to a range of adverse reactions, including hair loss, salivation, tremors, and numerous deaths in cats and kittens. In the short term, the agreement called for new warning labels on the products.

As of March 31, 2006, the sale and distribution of Hartz's phenothrin-containing flea and tick products for cats has been terminated. However, EPA's product cancellation order did not apply to Hartz flea and tick products for dogs, and Hartz continues to produce many of its flea and tick products for dogs.[8]

See also

References

  1. ↑ "d-Phenothrin". National Pesticide Information Center. Retrieved 2016-02-29.
  2. 1 2 3 4 5 6 7 JOURNAL OF PESTICIDE REFORM/ SUMMER 2003 • VOL. 23, NO. 2 "Archived copy". Archived from the original on 2012-07-04. Retrieved 2012-08-16.
  3. ↑ "Permethrin, Resmethrin, d-Phenothrin (Sumithrin®): Synthetic Pyrethroids For Mosquito Control". US EPA.
  4. ↑ Barros, Alfredo Carlos Simões Dornellas de; Sampaio, Marcelo de Castro Moura (2012). "Gynecomastia: physiopathology, evaluation and treatment". Sao Paulo Medical Journal. 130 (3): 187–197. doi:10.1590/S1516-31802012000300009. ISSN 1516-3180. PMID 22790552. Reinforcing the evidence suggesting that there is a relationship between chemicals and GM, it is worthwhile mentioning the epidemic onset observed among Haitian refugees in 1981 about four months after arrival in United States detention centers.22 After analyzing all identifiable environmental exposures, it was then found that phenothrin, a multi-insecticide contained in sprays that they had used was the causative agent.23 It is now widely known that phenothrin has antiandrogenic activity.
  5. ↑ Brody, MD, PhD, FACE, Steven A.; Loriaux, MD, D. Lynn (2003). "EPIDEMIC OF GYNECOMASTIA AMONG HAITIAN REFUGEES: EXPOSURE TO AN ENVIRONMENTAL ANTIANDROGEN". Endocrine Practice. 9 (5): 370–375. doi:10.4158/EP.9.5.370. ISSN 1530-891X.
  6. ↑ Phenothrin and s-Methoprene; Product Cancellation Order, US Environmental Protection Agency
  7. ↑ Phenothrin; Amendment to Terminate Use, US Environmental Protection Agency
  8. ↑ "Archived copy". Archived from the original on 2009-06-06. Retrieved 2009-05-20. See also "dog" in the following EPA ruling: "Insect Growth Regulators: S-Hydroprene (128966), S-Kinoprene (107502), Methoprene (105401), S-Methoprene (105402) Fact Sheet". U.S. Environmental Protection Agency. Archived from the original on 2009-06-24.
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