| Revision as of 12:27, 23 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chem← Previous edit |
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{{Chembox |
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{{Chembox |
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| verifiedrevid = 446307449 |
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| verifiedrevid = 446308577 |
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| ImageFile = Chemical Structure of IR3535.png |
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| ImageFile = Ethyl butylacetylaminopropionate.svg |
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| ImageSize = 260px |
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| ImageAlt = IR3535 |
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| ImageSize = 250px |
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| ImageAlt = IR3535 |
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| IUPACName = ethyl 3-propanoate |
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| IUPACName = Ethyl ''N''-acetyl-''N''-butyl-β-alaninate |
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| PIN = |
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| PIN = Ethyl 3-(''N''-butylacetamido)propanoate |
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| OtherNames = 3--aminopropionic acid, ethyl ester |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = {{Unbulleted list |
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| EBAAP |
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| CASNo = 52304-36-6 |
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| β-alanine, ''N''-acetyl-''N''-butyl-, ethyl ester |
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| PubChem = 104150 |
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| IR3535 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Insect Repellent 3535 |
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| BAAPE |
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}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 52304-36-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 65GQA237EH |
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| PubChem = 104150 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 94028 |
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| ChemSpiderID = 94028 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = VZRKEAFHFMSHCD-UHFFFAOYSA-N |
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| StdInChIKey = VZRKEAFHFMSHCD-UHFFFAOYSA-N |
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| SMILES = CCCCN(CCC(=O)OCC)C(=O)C}} |
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| SMILES = CCCCN(CCC(=O)OCC)C(=O)C}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=11 | H=21 | N=1 | O=3 |
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| Formula = C<sub>11</sub>H<sub>21</sub>NO<sub>3</sub> |
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| Appearance = Colorless liquid |
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| MolarMass = 215.28934 |
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| Odor = Almost odorless |
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| Appearance = |
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| Density = |
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| Density = 0.998 g/cm<sup>3</sup> (at 20 °C) |
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| MeltingPt = |
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| MeltingPt = < -90 °C |
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| BoilingPt = |
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| BoilingPt = 141 °C (decomposes) |
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| LogP = 1.7 (at 23 °C) |
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| Solubility = }} |
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| Solubility = 70 g/L (at 20 °C) |
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| Section3 = {{Chembox Hazards |
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| SolubleOther = >250 g/L (at RT) |
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| MainHazards = Biopesticide |
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| Solvent = Acetone, ethyl acetate, dichloromethane, ''n''-heptane, methanol, ''p''-xylene |
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| FlashPt = |
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| Autoignition = }} |
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|Section3={{Chembox Hazards |
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| FlashPtC = 159 |
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| GHSPictograms = {{GHS exclamation mark}} |
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| GHSSignalWord = '''Warning''' |
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| HPhrases = {{H-phrases| 319}} |
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| PPhrases = {{P-phrases| 280 | 305+351+338 | 337+313}} |
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| LD50 = {{Unbulleted list |
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| >5000 mg/kg (rat, oral) |
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|10000 mg/kg (rate, dermal) |
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|>5.1 mg/L (rat, inhalation)}} |
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'''Ethyl butylacetylaminopropionate''' is an ] whose trade name is '''IR3535''' and was developed and commercialized by ] (Germany). It is a colorless and odorless oil with a good skin feel in final products, and it is ].<ref name=":0"></ref><ref name=":1"></ref><ref name=":2"></ref> |
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Unlike ], IR3535 can dissolve some plastics and synthetic fabrics, except ] and ].<ref>{{cite web |title=Insect Repellent - FAQ |url=https://www.merckgroup.com/en/expertise/cosmetics/care-solutions/insect-repellent/faq.html |publisher=Merck |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230922130527/https://www.emdgroup.com/en/expertise/cosmetics/care-solutions/insect-repellent/faq.html |archive-date=22 September 2023 |url-status=live |quote=Like a number of other repellents, IR3535® is not compatible with certain synthetic materials.}}</ref><ref name="ewg2018">{{cite web |title=EWG’s 2018 Guide to Bug Repellents |url=https://www.ewg.org/consumer-guides/ewgs-2018-guide-bug-repellents |publisher=Environmental Working Group |access-date=9 August 2023 |date=17 July 2018 |archive-url=https://web.archive.org/web/20210410185511/https://www.ewg.org/consumer-guides/ewgs-2018-guide-bug-repellents |archive-date=10 April 2021 |url-status=live}}</ref><ref name="ncpc">{{cite web |title=Insect Repellents |url=https://www.poison.org/articles/insect-repellent |publisher=National Capital Poison Center |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230601091355/https://www.poison.org/articles/insect-repellent |archive-date=1 June 2023 |url-status=live |quote=IR3535 20% offers protection against Aedes and Culex mosquitoes for 7-10 hours but only 3.8 hours of protection against Anopheles in some studies. Therefore, IR3535 is not recommended for use in malaria-endemic areas. It is a serious eye irritant but otherwise has a good safety profile. It can melt some plastics and damage some fabrics.}}</ref> |
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'''IR3535''' is an insect repellent found in ] '''Skin So Soft''' line of topical insect repellents. ] is the registered trademark owner of IR3535 in the United States.<ref></ref> IR3535 is a synthetic ] that is additionally classified as '''biopesticide'''<ref></ref> by the ]. It was used in Europe 20 years prior to its registration with the EPA as an active ingredient in February 1999.<ref></ref> |
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== Effectiveness == |
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IR3535 is effective in repelling several different insects such as mosquitoes species and also ], ] and ]. It is as effective as ] against '']'' and '']'' mosquitoes, but may be less effective than DEET against '']'' mosquitoes, vectors of ].<ref name="jtm2010">{{Cite journal |vauthors=Goodyer LI, Croft AM, Frances SP, Hill N, Moore SJ, Onyango SP, Debboun M |display-authors=6 |date=1 May 2010 |title=Expert Review of the Evidence Base for Arthropod Bite Avoidance |url=https://academic.oup.com/jtm/article-lookup/doi/10.1111/j.1708-8305.2010.00402.x |journal=Journal of Travel Medicine |volume=17 |issue=3 |pages=182–192 |doi=10.1111/j.1708-8305.2010.00402.x |issn=1195-1982}}</ref><ref>{{Cite journal |last=Diaz |first=James H. |date=March 2016 |title=Chemical and Plant-Based Insect Repellents: Efficacy, Safety, and Toxicity |url=https://linkinghub.elsevier.com/retrieve/pii/S1080603215004342 |journal=Wilderness & Environmental Medicine |volume=27 |issue=1 |pages=153–163 |doi=10.1016/j.wem.2015.11.007|doi-access=free }}</ref> |
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A 2013 review concluded that IR3535 is as effective as 20% ] against ''Anopheles'', citing that some studies reported possibly shorter protection of just 3.8 hours.<ref name="tmid2013">{{Cite journal |vauthors=Lupi E, Hatz C, Schlagenhauf P |date=November 2013 |title=The efficacy of repellents against Aedes, Anopheles, Culex and Ixodes spp. – A literature review |url=https://linkinghub.elsevier.com/retrieve/pii/S1477893913001737 |journal=Travel Medicine and Infectious Disease |volume=11 |issue=6 |pages=374–411 |doi=10.1016/j.tmaid.2013.10.005}}</ref><ref name="ncpc"/> In areas with malaria, the NHS recommends 50% DEET or at least 30% DEET or 20% ] instead of IR3535.<ref>{{cite web |title=Malaria |url=https://www.nhs.uk/conditions/malaria/ |publisher=NHS |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230730193653/https://www.nhs.uk/conditions/malaria/ |archive-date=30 July 2023 |quote=use insect repellent on your skin – make sure it's 50% DEET-based |url-status=live}}</ref><ref>{{cite web |title=Mosquito bite avoidance: advice for travellers |url=https://www.gov.uk/government/publications/mosquito-bite-avoidance-for-travellers/mosquito-bite-avoidance-advice-for-travellers--2 |publisher=Gov.uk |access-date=22 September 2023 |archive-url=https://web.archive.org/web/20230124113031/https://www.gov.uk/government/publications/mosquito-bite-avoidance-for-travellers/mosquito-bite-avoidance-advice-for-travellers--2 |archive-date=24 January 2023 |url-status=live |quote=A product with 50% DEET is recommended as a first choice. If DEET is not tolerated, use of a repellent containing the highest strength formulation available of either icaridin (20%), eucalyptus citriodora oil, hydrated, cyclised or 3-ethlyaminopropionate is recommended.}}</ref><ref>{{Cite web |last=Team |first=HPS Travel Health |title=Mosquito Bite Avoidance - Fit for Travel |url=https://www.fitfortravel.nhs.uk/advice/malaria/mosquito-bite-avoidance.aspx |access-date=2023-08-07 |website=Fit for Travel |archive-url=https://web.archive.org/web/20230807160632/https://www.fitfortravel.nhs.uk/advice/malaria/mosquito-bite-avoidance.aspx |archive-date=7 August 2023 |url-status=live |quote=IR3535: less effective than DEET or Icaridin at preventing bites from the type of mosquitos that carry malaria; should not be used in countries where malaria is present}}</ref> IR3535, among other repellents, is included in the ] (WHO) recommendation for areas with malaria. The WHO also notes that it may be necessary to reapply repellents every 3-4 hours in hot and humid climates.<ref>{{Cite news |date=2023-03-29 |title=Malaria |url=https://www.who.int/news-room/fact-sheets/detail/malaria |access-date=2023-09-29 |publisher=World Health Organization}}</ref><ref>{{cite book |date=2020 |title=International Travel and Health |url=https://www.who.int/publications/i/item/9789241580472 |chapter=Malaria |publisher=World Health Organization |isbn=978-92-4-158047-2 |access-date=2023-09-30 |chapter-url=https://cdn.who.int/media/docs/default-source/travel-and-health/9789241580472-eng-chapter-7.pdf}}</ref> |
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IR3535 also helps prevent bites from ticks that may transmit ].<ref name="ncpc"/> |
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== Adverse effects == |
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IR3535 can irritate the eyes on contact.<ref name="ewg2018"/> |
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== Interactions == |
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Few if any studies have evaluated possible interactions when using IR3535 with sunscreens.<ref>{{cite web |title=Insect Repellents |url=http://npic.orst.edu/factsheets/repellents.html |publisher=National Pesticide Information Center |access-date=26 September 2023 |archive-url=https://web.archive.org/web/20230913011642/http://npic.orst.edu/factsheets/repellents.html |archive-date=13 September 2023 |date=February 2018 |url-status=live |quote=Few or no studies address using IR3535 or oil of lemon eucalyptus with sunscreens.}}</ref> |
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== Mechanism of action == |
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The mechanism of action is still under investigation, but it probably related to the intolerance of mosquitos and other invertebrate animals to its odor. |
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IR3535 is applied topically in human skin and prevent bites from mosquitos and ticks that might cause serious diseases, such as ], ], ], ], ], among others.<ref>{{Cite journal|last=Lo|first=Wai Ling|last2=Mok|first2=Ka Leung|last3=Yu Pui Ming|first3=Stephanie Dorothy|date=2018-09-01|title=Which insect repellents should we choose? Implications from results of local market survey and review of current guidelines|url=https://doi.org/10.1177/1024907918773630|journal=Hong Kong Journal of Emergency Medicine|language=en|volume=25|issue=5|pages=272–280|doi=10.1177/1024907918773630|issn=1024-9079|doi-access=free}}</ref> |
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== Chemistry == |
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== Chemistry == |
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The structure of IR3535 is based on ]<ref></ref> and ].<ref></ref> and the EPA has classified IR3535 as a biochemical substance based on the fact that it is "functionally identical" to beta alanine: both repel insects and the end groups of IR3535 are not likely to contribute to toxicity. <ref></ref> |
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IR3535 is a ] of non-proteinogenic amino acid ].<ref name=":1" /> |
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{{clear-left}} |
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== Approval == |
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IR3535 is approved by several authorities around the world, including ] (Europe)<ref>{{cite web |author1=Belgium (competent authority) |title=Regulation (EU) 528/2012 evaluation of active substances / Assessment Report / Ethyl butylacetylaminopropionate / Product-type 19 (insect repellent) |url=https://echa.europa.eu/documents/10162/aaf5b78c-82ca-40a3-25a4-1cc4339c9407 |date=March 13, 2014}}</ref> and the ] (US)<ref>{{cite web |last1=Environmental Protection Agency |title=3--aminopropionic acid, ethyl ester (IR3535) Interim Registration Review Decision Case Number 6046 |url=https://www.regulations.gov/document/EPA-HQ-OPP-2014-0106-0009 |website=www.regulations.gov |date=Feb 3, 2020}}</ref> where it is considered a biopesticide. |
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== See also == |
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== See also == |
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* ] |
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* ] |
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* ] |
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* ] (PMD) |
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* ], a ] ] that can be applied to clothing to help prevent bites |
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:{{clear-left}} |
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== References == |
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== References == |
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{{Reflist}} |
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<references/> |
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== External links == |
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== External links == |
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* {{cite journal | doi = 10.1603/0022-2585-39.6.895 | pmid = 12495189 | url = http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf | archive-url = https://web.archive.org/web/20110721072133/http://ddr.nal.usda.gov/bitstream/10113/6633/1/IND23332072.pdf | url-status = dead | archive-date = 2011-07-21 | title = Repellency of IR3535, KBR3023, para-menthane-3,8-diol, and DEET to Black Salt Marsh Mosquitoes (Diptera: Culicidae) in the Everglades National Park| journal = Journal of Medical Entomology| volume = 39| issue = 6| pages = 895–899| year = 2002| last1 = Barnard| first1 = Donald R.| last2 = Bernier| first2 = Ulrich R.| last3 = Posey| first3 = Kenneth H.| last4 = Xue| first4 = Rui-De| doi-access = free}} |
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{{DEFAULTSORT:Ir3535}} |
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{{organic-compound-stub}} |
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