Pyriproxyfen#Rumor of link to microcephaly outbreak in Brazil

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464377463

| Name = Pyriproxyfen

| ImageFile = Pyriproxyfen.svg

| ImageName = Chemical structure of pyriproxyfen

| IUPACName = 4-Phenoxyphenyl (R/S)-2-(2-pyridyloxy)propyl ether
2-[1-(4-Phenoxyphenoxy)propan-2-yloxy]pyridine

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 82851

| PubChem = 91753

| InChI = 1/C20H19NO3/c1-16(23-20-9-5-6-14-21-20)15-22-17-10-12-19(13-11-17)24-18-7-3-2-4-8-18/h2-14,16H,15H2,1H3

| InChIKey = NHDHVHZZCFYRSB-UHFFFAOYAG

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 39260

| SMILES = O(c1ncccc1)C(COc3ccc(Oc2ccccc2)cc3)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H19NO3/c1-16(23-20-9-5-6-14-21-20)15-22-17-10-12-19(13-11-17)24-18-7-3-2-4-8-18/h2-14,16H,15H2,1H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = NHDHVHZZCFYRSB-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 95737-68-1

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 3Q9VOR705O

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C18605

}}

|Section2={{Chembox Properties

| C=20 | H=19 | N=1 | O=3

| MeltingPtC = 48-50

| MeltingPt_ref = {{cite web | url =https://cdn.who.int/media/docs/default-source/wash-documents/wash-chemicals/pyriproxyfen-background.pdf| archive-url =https://web.archive.org/web/20090727072356/http://www.who.int/whopes/quality/en/pyriproxyfen_eval_specs_WHO_jul2006.pdf | url-status =dead | archive-date =July 27, 2009 | title = WHO Specifications and Evaluations for Public Health Pesticides: Pyriproxifen }}

| BoilingPtC = 318

| BoilingPt_ref =

| Density = 1.2 g/cm3{{Cite web | url = https://www.cdc.gov/niosh/ipcsneng/neng1269.html | title = Pyriproxifen | publisher = National Institute for Occupational Safety and Health}}

| Solubility = 0.367 mg/L

| Appearance = Colorless crystals

}}

|Section6={{Chembox Pharmacology

| ATCvet = yes

| ATCCode_prefix = P53

| ATCCode_suffix = AX23

}}

}}

Pyriproxyfen is a pesticide which is found to be effective against a variety of insects.{{cite journal | author1 = Ishaaya, I | author2 = Horowitz, AR | title = Pyriproxyfen, a Novel Insect Growth Regulator for Controlling Whiteflies : Mechanisms and Resistance Management | journal = Pestic. Sci. | year = 1995 | volume = 43 | pages = 227–232 | doi = 10.1002/ps.2780430308 | issue = 3}} It was introduced to the US in 1996, to protect cotton crops against whitefly. It has also been found useful for protecting other crops.{{cite book |last=Devillers |first=James |date=May 6, 2013 |title=Juvenile Hormones and Juvenoids: Modeling Biological Effects and Environmental Fate |url=https://books.google.com/books?id=4FDOBQAAQBAJ&dq |publisher=CRC Press |pages=108–126 |isbn=9781466513228}} It is also used as a prevention for flea control on household pets, for killing indoor and outdoor ants and roaches.{{cite book |last1=Maddison |first1=Jill E. |last2=Page |first2=Stephen W. |last3=Church |first3=David |date=2008 |title=Small Animal Clinical Pharmacology |url=https://books.google.com/books?id=RpsROVqemk8C&dq |publisher=Elsevier Health Sciences |page=226 |isbn=9780702028588}} Methods of application include aerosols, bait, carpet powders, foggers, shampoos and pet collars.{{Cite web

| url = https://www.federalregister.gov/articles/2012/12/12/2012-29978/pyriproxyfen-pesticide-tolerances

| title = Federal Register {{!}} Pyriproxyfen; Pesticide Tolerances

| website = www.federalregister.gov

| access-date = 2016-02-28

}}

Pyriproxyfen is a juvenile hormone analog (IRAC group 7C) and an insect growth regulator.{{cite web | url = http://npic.orst.edu/factsheets/pyriprogen.html | title = PyriproxyfenGeneral Fact Sheet | publisher = National Pesticide Information Center, Oregon State University Extension Services}} It prevents larvae from developing into adulthood and thus rendering them unable to reproduce.{{cite news |last=Szabo |first=Liz |date=February 16, 2016 |title=Scientists debunk theory linking pesticide, not Zika, to birth defects |url=https://www.usatoday.com/story/news/2016/02/16/experts-dismiss-claims-pesticide-not-zika-causes-birth-defects/80451116/ |newspaper=USA Today |access-date=February 16, 2016}}

In the US, pyriproxyfen is often marketed under the trade name Nylar,{{cite book |last=Goss |first=G. Robert |date=1997 |title=Pesticide Formulations and Application Systems |url=https://books.google.com/books?id=z0TJu0MeUx4C&dq |publisher=ASTM International |pages=87–93 |isbn=9780803124691}} and is one of two active ingredients in Advantage II. In Europe, pyriproxyfen is known under the brand names Cyclio (Virbac){{cite book |last1=Rock |first1=Amanda |last2=Bowden |first2=Sally |last3=Cousquer |first3=Glen |date=2007 |title=Veterinary Pharmacology: A Practical Guide for the Veterinary Nurse |url=https://books.google.com/books?id=Mu5Vn3Vi79oC&dq |publisher=Elsevier Health Sciences |page=96 |isbn=9780750688628}} and Exil Flea Free TwinSpot (Emax).

Toxicity in mammals

Pyriproxyfen has low acute toxicity.{{Cite web | url = http://inchem.org/documents/jmpr/jmpmono/v99pr12.htm | title = Toxicological evaluations | website = inchem.org | access-date = 2016-04-13 | quote = ...it was not necessary to establish an acute reference dose because of the low acute toxicity of pyriproxyfen.}} According to WHO and FAO, at elevated doses exceeding 5000 mg/kg of body weight, pyriproxyfen affects the liver in mice, rats and dogs.{{Cite web

| url = http://inchem.org/documents/jmpr/jmpmono/v99pr12.htm

| title = Toxicological evaluations

| website = inchem.org

| access-date = 2016-02-28

}} It also changes cholesterol levels, and may cause modest anemia at high doses.{{Cite web

| url =https://www.who.int/water_sanitation_health/dwq/chemicals/pyriproxyfen2ndadd.pdf

| title = Pyriproxyfen in Drinking-water, Background document for development of WHO Guidelines for Drinking-water Quality

}}

See also

References

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