metofluthrin

{{short description|Pyrethroid used as an insect repellent}}

{{Chembox

| Watchedfields = changed

| verifiedrevid = 448823374

| ImageFile = Metofluthrin.svg

| ImageSize = 230px

| IUPACName = 2,3,5,6-Tetrafluoro-4-(methoxymethyl)benzyl 2,2-dimethyl-3-(prop-1-en-1-yl)cyclopropanecarboxylate

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 240494-70-6

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = WZX356S299

| PubChem = 656636

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

| ChemSpiderID = 570989

| ChEBI = 79396

| KEGG = C13487

| SMILES = Fc1c(F)c(c(F)c(F)c1COC(=O)C2C(C=CC)C2(C)C)COC

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

| StdInChI = 1S/C18H20F4O3/c1-5-6-11-12(18(11,2)3)17(23)25-8-10-15(21)13(19)9(7-24-4)14(20)16(10)22/h5-6,11-12H,7-8H2,1-4H3

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

| StdInChIKey = KVIZNNVXXNFLMU-UHFFFAOYSA-N

| InChI = 1/C18H20F4O3/c1-5-6-11-12(18(11,2)3)17(23)25-8-10-15(21)13(19)9(7-24-4)14(20)16(10)22/h5-6,11-12H,7-8H2,1-4H3

| InChIKey = KVIZNNVXXNFLMU-UHFFFAOYAX

}}

|Section2={{Chembox Properties

| C=18 | H=20 | F=4 | O=3

| Appearance =

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|Section3={{Chembox Hazards

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Metofluthrin is a pyrethroid used as an insect repellent.{{cite book | author = Metofluthrin: novel pyrethroid insecticide and innovative mosquito control agent | title = Pesticide Chemistry | year = 2007 | pages = 149–158 | doi = 10.1002/9783527611249.ch16 | chapter = Metofluthrin: Novel Pyrethroid Insecticide and Innovative Mosquito Control Agent | isbn = 978-3-527-61124-9}} The vapors of metofluthrin are highly effective and capable of repelling up to 97% of mosquitoes in field tests.{{Cite journal | pmid = 17536367 | year = 2007 | last1 = Lucas | first1 = JR | last2 = Shono | first2 = Y | last3 = Iwasaki | first3 = T | last4 = Ishiwatari | first4 = T | last5 = Spero | first5 = N | last6 = Benzon | first6 = G | title = U.S. Laboratory and field trials of metofluthrin (SumiOne) emanators for reducing mosquito biting outdoors | volume = 23 | issue = 1 | pages = 47–54 | journal = Journal of the American Mosquito Control Association | doi=10.2987/8756-971x(2007)23[47:ulafto]2.0.co;2| s2cid = 42229041 }} Metofluthrin is used in a variety of consumer products, called emanators, for indoor and outdoor use.[https://web.archive.org/web/20190224221623/https://www.cdpr.ca.gov/docs/registration/ais/publicreports/5943.pdf Active Ingredient: Metofluthrin. Archived], California Department of Pesticide Regulation Public Report 2007-6{{cite web | url = http://pmep.cce.cornell.edu/profiles/insect-mite/fenitrothion-methylpara/metofluthrin/metoflu_reg_0608.pdf | title = Registration of OFF! Insect Repellent Fan }} These products produce a vapor that protects an individual or area. Effectiveness is reduced by air movement. Metofluthrin is neurotoxic, and is not meant to be applied directly to human skin.{{cite web | url = https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-109709_01-Sep-06.pdf | title = Metofluthrin pesticide fact sheet | publisher = U.S. Environmental Protection Agency }}

Although metofluthrin has insecticidal properties against the sand fly, Phlebotomus sergenti, it is not an effective repellent of this insect.{{Cite journal | pmid = 21366769 | year = 2011 | last1 = Zollner | first1 = G | last2 = Orshan | first2 = L | title = Evaluation of a metofluthrin fan vaporizer device against phlebotomine sand flies (Diptera: Psychodidae) in a cutaneous leishmaniasis focus in the Judean Desert, Israel | volume = 36 | pages = S157–65 | doi = 10.1111/j.1948-7134.2011.00126.x | journal = Journal of Vector Ecology| issue = Suppl 1 | url = https://apps.dtic.mil/sti/pdfs/ADA549712.pdf | archive-url = https://web.archive.org/web/20170927034503/http://www.dtic.mil/get-tr-doc/pdf?AD=ADA549712 | url-status = live | archive-date = September 27, 2017 | doi-access = free }}