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Revision as of 12:09, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 452823880 of page Pyriproxyfen for the Chem/Drugbox validation project (updated: '').		Latest revision as of 17:46, 15 December 2024 edit Bosula (talk | contribs)Extended confirmed users596 edits add IRAC groupTag: Visual edit
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 444077286
			| Watchedfields = changed
⚫	| Name = Pyriproxyfen
		⚫	| verifiedrevid = 464377463
	| ImageFile = Pyriproxyfen.svg
		⚫	| Name = Pyriproxyfen
	<!-- | ImageSize = 360px -->
	| ImageName = Chemical structure of pyriproxyfen		| ImageFile = Pyriproxyfen.svg
			| ImageName = Chemical structure of pyriproxyfen
	| IUPACName = 4-phenoxyphenyl (RS)-2-(2-pyridyloxy)propyl ether<br /> 2-pyridine		| IUPACName = 4-Phenoxyphenyl (''R/S'')-2-(2-pyridyloxy)propyl ether<br /> 2-pyridine
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 82851		| ChemSpiderID = 82851
	| PubChem = 91753		| PubChem = 91753
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 95737-68-1		| CASNo = 95737-68-1
			| UNII_Ref = {{fdacite|changed|FDA}}
			| UNII = 3Q9VOR705O
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C18605		| KEGG = C18605
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
			| C=20 | H=19 | N=1 | O=3
	| Formula = C<sub>20</sub>H<sub>19</sub>NO<sub>3</sub>
			| MeltingPtC = 48-50
	| MolarMass = 321.369 g/mol
			| MeltingPt_ref = <ref name=WHO>{{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 }}</ref>
	| MeltingPt = 46 °C
			| BoilingPtC = 318
	| Density = 1.2 g/cm³
			| BoilingPt_ref = <ref name=WHO/>
			| Density = 1.2 g/cm<sup>3</sup><ref name=CDC>{{Cite web | url = https://www.cdc.gov/niosh/ipcsneng/neng1269.html | title = Pyriproxifen | publisher = National Institute for Occupational Safety and Health}}</ref>
			| Solubility = 0.367 mg/L<ref name=WHO/>
			| Appearance = Colorless crystals<ref name=CDC/>
	}}		}}
			|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 ]s.<ref>{{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}}</ref> It was introduced to the US in 1996, to protect cotton crops against ]. It has also been found useful for protecting other crops.<ref>{{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=] |pages=108–126 |isbn=9781466513228}}</ref> It is also used as a prevention for flea control on household pets, for killing indoor and outdoor ants and roaches.<ref>{{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=] |page=226 |isbn=9780702028588}}</ref> Methods of application include aerosols, bait, carpet powders, foggers, shampoos and pet collars.<ref>{{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
			}}</ref>
			Pyriproxyfen is a ] (] group 7C) and an ].<ref>{{cite web | url = http://npic.orst.edu/factsheets/pyriprogen.html | title = PyriproxyfenGeneral Fact Sheet | publisher = National Pesticide Information Center, Oregon State University Extension Services}}</ref> It prevents larvae from developing into adulthood and thus rendering them unable to reproduce.<ref>{{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=] |access-date=February 16, 2016}}</ref>
			In the US, pyriproxyfen is often marketed under the trade name Nylar,<ref>{{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=] |pages=87–93 |isbn=9780803124691}}</ref> and is one of two active ingredients in Advantage II. In Europe, pyriproxyfen is known under the brand names Cyclio (])<ref>{{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=] |page=96 |isbn=9780750688628}}</ref> and Exil Flea Free TwinSpot (Emax).
			== Toxicity in mammals ==
			Pyriproxyfen has low acute toxicity.<ref name=inchem>{{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.}}</ref> According to ] and ], at elevated doses exceeding 5000&nbsp;mg/kg of ], pyriproxyfen affects the liver in mice, rats and dogs.<ref name=inchem2>{{Cite web
			| url = http://inchem.org/documents/jmpr/jmpmono/v99pr12.htm
			| title = Toxicological evaluations
			| website = inchem.org
			| access-date = 2016-02-28
			}}</ref> It also changes cholesterol levels, and may cause modest ] at high doses.<ref>{{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
			}}</ref>
			==Rumor of link to microcephaly outbreak in Brazil==
			{{broader|2015–16 Zika virus epidemic}}
			Starting in 2014, pyriproxifen was put into Brazilian water supplies to fight the proliferation of mosquito larvae.<ref></ref> This is in line with the ] (WHO)'s ] Evaluation Scheme (]) for ]s.<ref></ref> In January 2016, the Brazilian Association for Collective Health (''Abrasco''; {{langx|pt|Associação Brasileira de Saúde Coletiva}}) criticized the introduction of pyriproxyfen in Brazil. Abrasco demanded the "immediate suspension of pyriproxyfen and all growth inhibitors ... in drinking water." The organization is opposed to the use of growth inhibitors in the context of an ongoing outbreak of fetal malformation.<ref>{{cite web |url=https://www.abrasco.org.br/site/2016/02/nota-tecnica-sobre-microcefalia-e-doencas-vetoriais-relacionadas-ao-aedes-aegypti-os-perigos-das-abordagens-com-larvicidas-e-nebulizacoes-quimicas-fumace/ |trans-title=Technical note on microcephaly and vector diseases related to the ''Aedes aegypti'': the dangers of approaches using larvicides and chemical nebulization |title=Nota técnica sobre microcefalia e doenças vetoriais relacionadas ao ''Aedes aegypti'': os perigos das abordagens com larvicidas e nebulizações químicas – fumacê |publisher=Brazilian Association for Collective Health (Associação Brasileira de Saúde Coletiva, Abrasco) |quote=reivindicamos das autoridades competentes a adoção das medidas a seguir: ... (3) Nas medidas adotadas pelo MS para controle de Aedes aegypti em suas formas larva e adulto, imediata suspensão do Pyriproxyfen (0,5 G) e de todos os inibidores de crescimento como o Diflubenzuron e o Novaluron, ou qualquer outro produto químico ou biológico em água potável. |language=pt}}</ref>
			On February 3, the rumor that pyriproxyfen, not the ], is the cause of the 2015-2016 ] outbreak in ] was raised in a report of the Argentinean organization Physicians in the Crop-Sprayed Villages (PCST).<ref name="PCST">: ''“Malformations detected in thousands of children from pregnant women living in areas where the Brazilian state added pyriproxyfen to drinking water is not a coincidence, even though the Ministry of Health places a direct blame on Zika virus for this damage, while trying to ignore its responsibility and ruling out the hypothesis of direct and cumulative chemical damage caused by years of endocrine and immunological disruption of the affected population.,”'' PCST said.</ref> It attracted wide media coverage.<ref>{{cite web | url = http://www.theecologist.org/News/news_analysis/2987137/argentine_and_brazilian_doctors_suspect_mosquito_insecticide_as_cause_of_microcephaly.html | title = Argentine and Brazilian doctors suspect mosquito insecticide as cause of microcephaly | publisher = Ecologist}}</ref><ref>{{cite news |last=Almendrala |first=Anna |date=February 16, 2016 |title=A Viral Story Links The Zika Crisis To Monsanto. Don't Believe It. |url=http://www.huffingtonpost.com/entry/zika-monsanto-pyriproxyfen-microcephaly_us_56c2712de4b0b40245c79f7c |newspaper=] |access-date=February 16, 2016}}</ref>
			The statement from Abrasco was cited in the PCST report; subsequently, Abrasco clarified that position as a misinterpretation of their statement, saying "at no time did we state that pesticides, insecticides, or other chemicals are responsible for the increasing number of microcephaly cases in Brazil". They also condemned the behavior of the websites that spread the misinformation, adding that such "untruths...violates the anguish and suffering of the people in vulnerable positions".<ref name="BBC"></ref> In addition, the coordinator for the PCST statement, Medardo Ávila Vazquez, acknowledged in an interview that "the group hasn't done any lab studies or epidemiological research to support its assertions, but it argues that using larvicides may cause human deformities."<ref>{{cite news |last1=Johnson |first1=Reed |last2=Jelmayer |first2=Rogerio |date=February 15, 2016 |title=Brazil State Bans Pesticide After Zika Claim |url=https://www.wsj.com/articles/brazil-state-bans-pesticide-after-zika-claim-1455584596 |newspaper=] |access-date=February 16, 2016}}</ref>
			On February 13, the Brazilian state of ] suspended pyriproxyfen's use, citing both Abrasco and PCST positions.<ref></ref><ref></ref> The Health Minister of Brazil, Marcelo Castro, criticized this step, noting that the claim is "a rumor lacking logic and sense. It has no basis." They also noted that the insecticide is approved by the National Sanitary Monitoring Agency and "all regulatory agencies in the whole world". The manufacturer of the insecticide, ], stated "there is no scientific basis for such a claim" and also referred to the approval of pyriproxyfen by the ] since 2004 and the United States ] since 2001.<ref>{{cite news | url = http://latino.foxnews.com/latino/news/2016/02/14/brazilian-state-suspends-larvicide-used-to-combat-zika-virus/ | title = Brazilian state suspends larvicide used to combat Zika virus | publisher = Fox News Latino | date = February 14, 2016}}</ref><ref>{{cite news |url=http://www.sciencealert.com/argentinian-report-says-monsanto-linked-pesticide-is-to-blame-for-microcephaly-outbreak-not-zika |title=Report says Monsanto-linked pesticide is to blame for microcephaly outbreak - not Zika |work=Science Alert |date=16 February 2016 |access-date=2016-02-16 }}</ref>
			George Dimech, the director of Disease Control and Diseases of the Health Department of Pernambuco in Brazil, gave an interview to the ] where he pointed out that the city of ] has the current highest reported number of cases of microcephaly, yet pyriproxyfen is not used in the region, but another insecticide altogether. He added that "this lack of spatial correlation weakens the idea that the larvicide is the cause of the problem." In addition, the BBC interviewed researchers in Pernambuco, where no evidence has been found of the cases being linked to any environmental cause like an insecticide. Neurologist Vanessa van der Linden stated in an interview, "Clinically, the changes we see in the scans of babies suggest that the injuries were caused by congenital infection and not by larvicide, drug or vaccine."<ref name="BBC"/>
			Noted skeptic ] called the claim a ] and pointed out that ] proponents had also claimed that the ] vaccine was the cause of the microcephaly outbreak, due to its introduction in 2014, along with adding, "One can't help but wonder what else the Brazilian Ministry of Health did in 2014 that cranks can blame microcephaly on." Gorski also pointed out the extensive ] understanding of pyriproxyfen coded in the ], which concluded in a past evaluation that the insecticide is not ], and that the doctor organization making the claim has been advocating against all pesticides since 2010, complicating their reliability.<ref name="Gorski">{{cite web |url=http://scienceblogs.com/insolence/2016/02/15/say-it-aint-so-george-george-takei-falls-for-a-zika-virus-conspiracy-theory/ |title=Oh, myyyy! George Takei falls for a Zika virus conspiracy theory |last1=Gorski |first1=David |author-link=David Gorski |date=February 15, 2016 |website=Respectful Insolence |publisher=] |access-date=February 15, 2016}}</ref><ref name="who">{{cite web|title=Chemical hazards in drinking-water: Pyriproxyfen|url=https://www.who.int/water_sanitation_health/dwq/chemicals/pyriproxyfen/en/|archive-url=https://web.archive.org/web/20071014054118/http://www.who.int/water_sanitation_health/dwq/chemicals/pyriproxyfen/en/|url-status=dead|archive-date=October 14, 2007|website=who.int|publisher=World Health Organization|access-date=15 February 2016}}</ref><ref>EFSA (European Food Safety Authority), 2014. Conclusion on the peer review of the pesticide risk assessment of confirmatory data submitted for the active substance pyriproxyfen. EFSA Journal 2014;12(8):3813, 19 pp. doi:10.2903/j.efsa.2014.3813 Aces. Jan. 13</ref>
			A professor from the ] in Australia, stated that "The effect of pyriproxyfen on reproduction and fetal abnormalities is well studied in animals. In a variety of animal species even enormous quantities of pyriproxyfen do not cause the defects seen during the recent Zika outbreak."<ref name='scimex'>{{cite news |url=https://www.scimex.org/newsfeed/expert-reaction-is-a-pesticide,-not-zika-virus,-causing-microcephaly |title=EXPERT REACTION: Is a pesticide, not Zika virus, causing microcephaly? |work=SCIMEX |date=15 February 2016 |access-date=2016-02-16 }}</ref> A colleague also from the University of Adelaide stated that "While the evidence that Zika virus is responsible for the rise in microcephaly in Brazil is not conclusive, the role of pyriproxyfen is simply not plausible."<ref name='scimex'/> Another professor in Australia concluded that "insect development is quite different to human development and involves different hormones, developmental pathways and sets of genes, so it cannot be assumed that chemicals affecting insect development also influence mammalian development."<ref name='scimex'/>
			==See also==
			* ]
			==References==
			{{reflist|30em}}
			==External links==
			* {{PPDB|574|Name=Pyriproxyfen}}
			{{Insecticides}}
			]
			]
			]