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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 448891442
| Watchedfields = changed
| ImageFile = Cyfluthrin.png
| verifiedrevid = 449713431
| ImageSize = 200px
| ImageFile1 = Cyfluthrin Marco 201809017.svg
| IUPACName = [(R)-cyano-[4-fluoro-3-(phenoxy)phenyl]methyl] (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
| ImageFile2 = Cyfluthrin 3D.png
| PIN = (''R'')-Cyano(4-fluoro-3-phenoxyphenyl)methyl (1''R'',3''R'')-3-(2,2-dichloroethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
| OtherNames =
| OtherNames =
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 45482
| ChemSpiderID = 45482
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| CASNo = 68359-37-5
| CASNo = 68359-37-5
| PubChem = 50153
| PubChem = 50153
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ATCCode_prefix = P03
| ChEMBL = 2104608
| ATCCode_suffix = BA01
| ATC_Supplemental = {{ATCvet|P53|AC12}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10982
| KEGG = C10982
| SMILES = Cl/C(Cl)=C/[C@H]3[C@@H](C(=O)O[C@@H](C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C
| SMILES = Cl/C(Cl)=C/[C@H]3[C@@H](C(=O)O[C@@H](C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C
}}
}}
| Section2 = {{Chembox Properties
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| C=22 | H=18 | Cl=2 | F=1 | N=1 | O=3
| Formula =
| MolarMass = 434.288
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| Density =
| Density =
| MeltingPt =
| MeltingPtC = 60
| BoilingPt =
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| Solubility = }}
| Solubility = 2 μg/L}}
| Section3 = {{Chembox Hazards
|Section6={{Chembox Pharmacology
| ATCCode_prefix = P03
| ATCCode_suffix = BA01
| ATC_Supplemental = {{ATCvet|P53|AC12}}
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|Section7={{Chembox Hazards
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'''Cyfluthrin''' is a [[pyrethroid]] [[insecticide]] and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of [[isomer]]s. Like most pyrethroids (MoA 3a),<ref name="IRAC-MoAs-9.4" /> it is highly toxic to fish and [[invertebrates]], but it is far less toxic to humans.<ref name=Ullmann/> It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.
'''Cyfluthrin''' is a synthetic [[pyrethroid]] derivative that is used as an [[insecticide]] in [[restricted use pesticide]] and common household pesticide. Cyfluthrin is regulated by the EPA, and all products containing cyfluthrin in the U.S. must be registered with the EPA.<ref>{{cite web|url=http://www.epa.gov/oppsrrd1/reevaluation/pyrethroids-pyrethrins.html|title=Pyrethroids and Pyrethrins|publisher=United States Environmental Protection Agency}}</ref> Like most pyrethroids, it is highly toxic to fish, invertebrates, and insects because they lack the kind of protection that is provided by skin. Cyfluthrin is chemically similar to [[methyl isocyanate]] released into the air in Bhopal, India in December 1984, which caused thousands of deaths. Health and safety risks are controlled by [[Right to know]] laws that exist in most developed countries. <ref>{{cite web|url=http://www.umass.edu/sts/ethics/bhopal.html|title=IDEESE: Cases - Bhopal Plant Disaster|publisher=University of Massachusetts, Amherst}}</ref>


==Safety==
Environmental illness caused by pesticides, like cyfluthrin, share characteristics with common diseases. Exposure symptoms include numbness, tingling, itching, burning sensation, bronchitis, chest pain, dizziness, headache at low concentration following skin contact, mucous membrane contact, inhalation, or ingestion. Higher concentrations have more profound effects that include nausea, fatigue, weakness, vomiting, changes in awareness, convulsions, loss of consciousness, and asphyxiation. <ref>''Oregon State University Extension Toxicology Network - Cyfluthrin'',http://extoxnet.orst.edu/pips/cyfluthr.htm</ref><ref>{{cite book|author=Worthing, C.E. (ed.).|title=The Pesticide Manual: A World Compendium. Ninth edition.|publisher=The British Crop Protection Council.|year=1991}}</ref><ref>{{cite book|author=Anonymous|Title=Evaluations Part II Toxicology. Cyfluthrin. pp. 53-78.|publisher=JMPR|year=1987}}</ref> [[Influenza]], [[heart disease]], and [[asthma]] have the same symptoms. Failure to obtain proper disclosure will lead to improper and ineffective medical diagnosis and treatment.<ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6599|title=Cyfluthrin|publisher=Toxicology Data Network; National Library of Medicine}}</ref>
In rats, the {{LD50}}s are 500, 800 (oral), and 600 (skin) mg/kg.<ref name=Ullmann>{{cite book | author = Robert L. Metcalf | chapter = Insect Control | title = Ullmann's Encyclopedia of Industrial Chemistry | publisher = Wiley-VCH | location = Weinheim | year = 2002 | doi = 10.1002/14356007.a14_263| isbn = 9783527303854 }}</ref>


Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures. In humans, it is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, whose urinary excretion half-lives are in a range of 5–7 hours. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantification of cyfluthrin in blood or plasma.<ref>{{Cite book|author = R. Baselt | title = Disposition of Toxic Drugs and Chemicals in Man | edition = 8th | publisher = Biomedical Publications | location = Foster City, CA | year = 2008 | pages = 388–389}}</ref>
==Risks==


Health and safety risks are controlled by [[right to know]] laws that exist in most developed countries. Cyfluthrin is regulated in the US by the EPA.<ref>{{cite web|url=http://www.epa.gov/oppsrrd1/reevaluation/pyrethroids-pyrethrins.html|title=Pyrethroids and Pyrethrins|publisher=United States Environmental Protection Agency}}</ref>
Cyfluthrin contains [[cyanide]] according to the legal definition in United States law.<ref>{{cite web|url=http://www.law.cornell.edu/uscode/42/usc_sec_42_00007412----000-.html|title=Title 42 U.S.C. Section 7412.|publisher=Cornell School of Law}}</ref> It is a potentially lethal substance. Disclosure is required for all types of exposure and training is required for workplace exposure.<ref>{{cite web|url=http://www.law.cornell.edu/uscode/42/usc_sec_42_00007413----000-.html|title=Title 42 U.S.C. Section 7413.|publisher=Cornell School of Law}}</ref> Cyfluthrin is subject to [[Right to know]] laws governing public health.<ref>{{cite web|url=http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=standards&p_id=10099|title=Toxic and Hazardous Substances; Hazard Communication.|publisher=U.S. Occupation Safety and Health Administration}}</ref>


==See also==
Toxicity depends upon the route of entry into the body.
* [[Cyhalothrin]]
* [[Imiprothrin]]


==References==
[[Pyrethroids]] and [[cyanide]] compounds are detoxified to some extent by the liver when ingested. Cyfluthrin is a skin and eye irritant. Human skin tends to block pyrethroids, which are not absorbed very well. Cyfluthrin can cause numbness, itching, burning, stinging, and tingling following skin and mucous membrane contact. Lips, tung, sinus, throat, lungs, and eye tissue may swell. The onset of symptoms can take 1 or 2 days to appear after initial exposure but symptoms may also occur during exposure. Sweating or exposure to sun or heat may make skin irritation worse.<ref>''Oregon State University Extension Toxicology Network - Cyfluthrin'',http://extoxnet.orst.edu/pips/cyfluthr.htm</ref>
{{reflist|refs=


<ref name="IRAC-MoAs-9.4">{{cite web|url=http://irac-online.org/documents/moa-classification/|title=IRAC Mode of Action Classification Scheme Version 9.4|website=IRAC ([[Insecticide Resistance Action Committee]])|type=pdf|date=March 2020}}</ref>
Cyfluthin is absorbed readily during inhalation exposure where it is not detoxified by the liver. Aerosol and particle exposure can prove fatal either from [[cytochrome_c_oxidase]] or from [[Hemoglobin#Competitive|hemoglobin binding that damages red blood cells]]. Inhalation toxicity tests with rats shows [[median lethal dose]] is >1,089 ug/l in 1 hour tests, and ranged from 469 - 592 ug/l in 4 hour tests for the chemical cyfluthrin.<ref>{{cite book|author=Worthing, C.E. (ed.).|title=The Pesticide Manual: A World Compendium. Ninth edition.|publisher=The British Crop Protection Council.|year=1991}}</ref><ref>{{cite book|author=Anonymous|Title=Evaluations Part II Toxicology. Cyfluthrin. pp. 53-78.|publisher=JMPR|year=1987}}</ref>


}}
Cyfluthrin is the root cause of a number of industrial injuries that occur every year due to inadequate worker protection and improper public safety.<ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6599|title=Cyfluthrin|publisher=Toxnet, National Library of Medicine}}</ref>

The cyanide content of cyfluthin can contribute to the development of hypersensitivity disease, autoimmune disease, Alzheimer's disease, and other serious illnesses following repetitive sub-lethal exposure.<ref>{{cite web|url=http://www.atsdr.cdc.gov/toxprofiles/tp8-c8.pdf|title=Toxicological Profile for Cyanide|publisher=U.S. Department of Health: Centers for Disease Control}}</ref><ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+2130|title=Cyanogen: Human Health Effects|publisher=National Library for Medicine: Toxicology Data Network}}</ref><ref>{{cite web|url=http://www.atsdr.cdc.gov/MHMI/mmg8.html|title=Medical management guidelines for cyanide poisoning (US)|publisher=Agency for Toxic Substances and Disease Registry; United States Department of Health and Human Services}}</ref><ref>{{cite web|url=http://www.atsdr.cdc.gov/toxprofiles/tp8.pdf|title=Toxicological profile for cyanide|publisher=U.S. Department of Health and Human Services}}</ref>

Cyanide exposure plays a role in neurological diseases, such as multiple sclerosis, Alzheimer's, and dystonia.<ref>{{cite web|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2981078/|title=Mitochondria and disease progression in multiple sclerosis|publisher=U.S. National Library of Medicine}}</ref><ref>{{cite web|url=http://www.ncbi.nlm.nih.gov/pubmed/12551727|title=Acetylcholine reduces cyanide-induced superoxide anion generation and lipid peroxidation in rat brain homogenates.|publisher=U.S. National Library of Medicine}}</ref><ref>{{cite web|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1014725/pdf/jnnpsyc00488-0028.pdf|title=Delayed cyanide induced dystonia|publisher=U.S. National Library of Medicine}}</ref>

==Regulation==

Most developed countries have regulatory requirements similar to the United States.

===United States===

The chemical cyfluthrin is a [[restricted use pesticide]] registered and regulated by the [[United States Environmental Protection Agency]]. It is an ingredient in restricted use pesticides and it is an ingredient in common household pesticide sold to the public. Restricted use pesticides can only be purchased and supervised by a licensed pest control supervisor.<ref>{{cite web|url=http://www.epa.gov/opp00001/health/worker.htm|title=Worker Safety and Training|publisher=United States Environmental Protection Agency}}</ref> The list of restricted use pesticides is available to the public.<ref>{{cite web|url=http://www.epa.gov/opprd001/rup/|title=Restricted Use Products (RUP) Report|publisher=United States Environmental Protection Agency}}</ref>

Requirement for a Material Safety Data Sheet (MSDS) is identified in 42 U.S.C. §11021, which is enforced by Occupational Health and Safety Administration in the United States.<ref>{{cite web|url=http://www.law.cornell.edu/uscode/usc_sec_42_00011021----000-.html|title=§ 11021. MATERIAL SAFETY DATA SHEETS|publisher=Cornell University School of Law}}</ref><ref>{{cite web|url=http://www.osha.gov/dsg/hazcom/enforcementmsdsrequirement.html|title=Enforcement of Material Safety Data Sheet (MSDS) Requirement|publisher=Occupational Health and Safety Administration: United States Department of Labor}}</ref> The MSDS must be made readily available to all employees exposed to hazardous substances in the workplace.<ref>{{cite web|url=http://www.osha.gov/pls/oshaweb/owadisp.show_document?p_table=standards&p_id=10099|title=Toxic and Hazardous Substances: Hazard Communication|publisher=Occupational Health and Safety Administration: United States Department of Labor}}</ref> The manufacturer must make the MSDS available to the public upon request.

The [[United States Department of Transportation]] (DOT) regulates hazmat transportation within the territory of the US by ''Title 49 of the Code of Federal Regulations''<ref name="49FR">{{cite web| title=49 FR|url=http://hazmat.dot.gov/regs/rules.htm|publisher=[[United States Department of Transportation]]}}</ref>.

* [[Dangerous Goods]]

The safety and security of the public transportation system is enforced by Department of Transportation.<ref>{{cite web|url=http://www.fmcsa.dot.gov/safety-security/safety-security.htm|title=Safety and Security|publisher=Department of Transportation}}</ref> Department of transportation must be notified for spills and accidental discharge into the environment. DOT is responsible for enforcement actions and public notification regarding hazardous chemical releases and exposures, including incidents involving federal workers.

* [http://www.fmcsa.dot.gov/safety-security/hazmat/complyhmregs.htm How to Comply with Federal Hazardous Materials Regulations]

The Pipeline and Hazardous Material Safety Administration within the Department of Transportation is responsible for maintaining the list of hazardous materials within the United States.<ref>{{cite web|url=http://www.phmsa.dot.gov/hazmat/library|title=Library|publisher=Pipeline and Hazardous Material Safety Administration; Department of Transportation}}</ref>

Intentional discharge into the environment must be reported to state and local environmental monitoring agencies in the United States.

====California====

The [http://www.arb.ca.gov/capcoa/roster.htm Air Resources Board] is responsible for public hazard disclosures in California. <ref>{{cite web|url=http://www.arb.ca.gov/capcoa/roster.htm|title=California Local Air District Directory|publisher=California}}</ref>Pesticide use disclosures are made by each pest control supervisor to the County Agricultural Commission.<ref>{{cite web|url=http://www.cdpr.ca.gov/docs/county/comenu.htm/|title=County Agricultural Commissioner Resources|publisher=California Department of Pesticide Regulation}}</ref> [[Epidemiology]] information is available from the [http://calpip.cdpr.ca.gov/ California Pesticide Information Portal], which can be used by health care professionals to identify the cause for environmental illness.<ref>{{cite web|url=http://calpip.cdpr.ca.gov/|title=California Pesticide Information Portal|publisher=California}}</ref>

====Oregon====

Under the Oregon Community Right to Know Act (ORS 453.307-372) and the federal Superfund Amendments and Reauthorization Act (SARA) Title III, the Office of the State [[Fire Marshal]] collects information on hazardous substances and makes it available to emergency responders and to the general public.

==Medicine==

The medical treatment is to avoid contact. Cyfluthin is a [[neurotoxin]] fortified by [[cyanide]] and there is no antidote. Urine and blood tests are used to confirm exposure.<ref>{{cite web|url=http://www.atsdr.cdc.gov/phs/phs.asp?id=785&tid=153|title=Public Health Statement for Pyrethrins and Pyrethroids|publisher=Centers for Disease Control and Prevention}}</ref><ref>{{cite web|url=http://www.atsdr.cdc.gov/ToxProfiles/tp155-c2.pdf|title=Relevance to Public Health; Pyrethrins and Pyrethroids|publisher=Centers for Disease Control and Prevention}}</ref><ref>{{cite web|url=http://www.atsdr.cdc.gov/ToxProfiles/tp155-c3.pdf|title=Health Effects; Pyrethrins and Pyrethroids|publisher=Centers for Disease Control and Prevention}}</ref><ref>{{cite web|url=http://www.atsdr.cdc.gov/toxprofiles/tp155-c7.pdf|title=Analytical Methods; Pyrethrins and Pyrethroids|publisher=Centers for Disease Control and Prevention}}</ref><ref>{{cite web|url=http://www.cdc.gov/exposurereport/data_tables/Cyfluthrin_ChemicalInformation.html|title=Cyfluthrin; CAS No. 68359-37-5; National Report on Human Exposure to Environmental Chemicals|publisher=Centers for Disease Control and Prevention}}</ref>

Risk of injury and illness are reduced by worker training required by [[Occupational Safety and Health Administration]] for workplace exposure. This risk is also reduced by training and certification involving the [[Worker Protection Standard]] for licensed pest control supervisors and licensed pest control applicators.

Minimum risk levels (MRLs) may not protect for delayed health effects or health effects acquired following repeated sublethal exposure, such as hypersensitivity, asthma, or bronchitis. MRLs may be revised after sufficient data accumulates (Toxicological Profile for Cyanide, U.S. Department of Health and Human Services, 2006).

Pyrethroids, including cyfluthrin, interfere with the way nerves function, including the brain. Animal studies indicate pyrethrins and pyrethroids cause the kinds of cellular changes associated with cancer. Fatal allergic reactions have occurred following repetitive exposure.<ref>{{cite web|url=http://www.atsdr.cdc.gov/phs/phs.asp?id=785&tid=153|title=Public Health Statement for Pyrethrins and Pyrethroids|publisher=Agency for Toxic Substances and Disease Registry; Centers for Disease Control and Prevetion}}</ref>

Injuries within the United States involve from 100 to 350 people with approximately 1 death each year from this type of chemical.<ref>{{cite web|url=http://www.epa.gov/oppsrrd1/reevaluation/pyrethrins-pyrethroids-asthma-allergy-9-18-09.pdf|title=A Review of the Relationship between Pyrethrins, Pyrethroid Exposure and Asthma and Allergies|publisher=United States Environmental Protection Agency}}</ref> In humans, it is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, whose urinary excretion half-lives are in a range of 5–7 hours. Routine worker exposure is monitored by measuring urinary metabolites, while severe exposure is identified by detecting cyfluthrin in blood or plasma.<ref>R. Baselt, ''Disposition of Toxic Drugs and Chemicals in Man'', 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 388-389.</ref>

Medical treatment is limited to oxygen therapy and keeping the airway open until the effects decline after washing off any residue and isolation from the source of the exposure.<ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+6599|title=Cyfluthrin|publisher=Toxicology Data Network; National Library of Medicine}}</ref>Fatal allergic reactions have been seen following exposure to products that contain pyrethrins or pyrethroids.<ref>{{cite web|url=http://www.atsdr.cdc.gov/phs/phs.asp?id=785&tid=153|title=Public Health Statement for Pyrethrins and Pyrethroids|publisher=Agency for Toxic Substances and Disease Registry; Centers for Disease Control and Prevention}}</ref>

Vitamin B12 may help to reduce health risks related to the cyanide content.<ref>{{cite web|url=http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3119202/|title=Cobinamide is superior to other treatments in a mouse model of cyanide poisoning|publisher=National Library of Medicine}}</ref>

==References==
<references/>
{{Reflist}}

==See Also==


{{US Environmental law}}
{{medicine}}
{{insecticides}}
{{insecticides}}


[[Category:Organofluorides]]
[[Category:Fluoroarenes]]
[[Category:Organochlorides]]
[[Category:(cyano-(3-phenoxyphenyl)methyl) 2,2,3-trimethylcyclopropane-1-carboxylates]]
[[Category:Pyrethroids]]
[[Category:Pyrethroids]]
[[Category:Organochlorides]]
[[Category:Nitriles]]
[[Category:Phenol ethers]]
[[Category:Cyanide]]
[[Category:Industrial hygiene]]
[[Category:Safety engineering]]
[[Category:Environmental law]]
[[Category:Medicine| ]]
[[Category:Health sciences]]

{{organic-compound-stub}}

[[ca:Ciflutrina]]
[[cs:Cyfluthrin]]
[[de:Cyfluthrin]]
[[es:Ciflutrina]]
[[fr:Cyfluthrine]]
[[it:Ciflutrin]]
[[nl:Cyfluthrin]]
[[ja:シフルトリン]]
[[pl:Cyflutryna]]

Latest revision as of 04:00, 27 August 2023

Cyfluthrin
Names
Preferred IUPAC name
(R)-Cyano(4-fluoro-3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethen-1-yl)-2,2-dimethylcyclopropane-1-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.063.485 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1 checkY
    Key: QQODLKZGRKWIFG-QSFXBCCZSA-N checkY
  • InChI=1/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3/t15-,18-,20-/m0/s1
    Key: QQODLKZGRKWIFG-QSFXBCCZBF
  • Cl/C(Cl)=C/[C@H]3[C@@H](C(=O)O[C@@H](C#N)c2ccc(F)c(Oc1ccccc1)c2)C3(C)C
Properties
C22H18Cl2FNO3
Molar mass 434.29 g·mol−1
Melting point 60 °C (140 °F; 333 K)
2 μg/L
Pharmacology
P03BA01 (WHO) QP53AC12 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Cyfluthrin is a pyrethroid insecticide and common household pesticide. It is a complex organic compound and the commercial product is sold as a mixture of isomers. Like most pyrethroids (MoA 3a),[1] it is highly toxic to fish and invertebrates, but it is far less toxic to humans.[2] It is generally supplied as a 10–25% liquid concentrate for commercial use and is diluted prior to spraying onto agricultural crops and outbuildings.

Safety

[edit]

In rats, the LD50s are 500, 800 (oral), and 600 (skin) mg/kg.[2]

Excessive exposure can cause nausea, headache, muscle weakness, salivation, shortness of breath and seizures. In humans, it is deactivated by enzymatic hydrolysis to several carboxylic acid metabolites, whose urinary excretion half-lives are in a range of 5–7 hours. Worker exposure to the chemical can be monitored by measurement of the urinary metabolites, while severe overdosage may be confirmed by quantification of cyfluthrin in blood or plasma.[3]

Health and safety risks are controlled by right to know laws that exist in most developed countries. Cyfluthrin is regulated in the US by the EPA.[4]

See also

[edit]

References

[edit]
  1. ^ "IRAC Mode of Action Classification Scheme Version 9.4". IRAC (Insecticide Resistance Action Committee) (pdf). March 2020.
  2. ^ a b Robert L. Metcalf (2002). "Insect Control". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a14_263. ISBN 9783527303854.
  3. ^ R. Baselt (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 388–389.
  4. ^ "Pyrethroids and Pyrethrins". United States Environmental Protection Agency.
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