indoxacarb
{{Chembox
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| ImageFile = indoxacarb.svg
| ImageName = Stereo wireframe model of (4aS)-Indoxacarb
| PIN = Methyl 7-chloro-2,5-dihydro-2-
| SystematicName = (S)-Methyl 7-chloro-2-{[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl}-2H,3H,4aH,5H-indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
|Section1={{Chembox Identifiers
| Abbreviations = DPX-MP062
| CASNo = 173584-44-6
| CASNo_Ref = {{Cascite|correct|CAS}}
| PubChem = 107720
| ChemSpiderID = 96889
| UNNumber = UN 3077
| MeSHName = Indoxacarb
| KEGG = D06316
| ChEBI = 38630
| ChEMBL = 197676
| UNII = 52H0D26MWR
| SMILES = COC(=O)N(C(=O)N1COC2(C(=O)OC)Cc3cc(Cl)ccc3C2=N1)c1ccc(OC(F)(F)F)cc1
| InChI = 1S/C22H17ClF3N3O7/c1-33-18(30)21-10-12-9-13(23)3-8-16(12)17(21)27-28(11-35-21)19(31)29(20(32)34-2)14-4-6-15(7-5-14)36-22(24,25)26/h3-9H,10-11H2,1-2H3
| InChIKey = VBCVPMMZEGZULK-UHFFFAOYSA-N
| Beilstein = 8366683}}
|Section2={{Chembox Properties
| C=22 | H=17 | Cl=1 | F=3 | N=3 | O=7
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| MeltingPtC = 88.1
| MeltingPt_notes = 99% indoxacarb PAI
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|Section6={{Chembox Pharmacology
| ATCvet = yes
| ATCCode_prefix = P53
| ATCCode_suffix = AX27
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Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae.{{Cite book |last1=Jeschke |first1=Peter |url=https://onlinelibrary.wiley.com/doi/book/10.1002/9783527699261 |title=Modern Crop Protection Compounds |last2=Witschel |first2=Matthias |last3=Krämer |first3=Wolfgang |last4=Schirmer |first4=Ulrich |date=25 January 2019 |publisher=Wiley-VCH |isbn=9783527699261 |edition=3rd |pages=1424–1448 |chapter=33.4 Voltage-dependent Sodium Channel-blocking Insecticides|doi=10.1002/9783527699261 }} It is marketed under the names Indoxacarb Technical Insecticide, Steward Insecticide and Avaunt Insecticide. It is also used as the active ingredient in the Syngenta line of commercial pesticides: Advion and Arilon.[http://www.epa.gov/opprd001/factsheets/indoxacarb.pdf United States Environmental Protection Agency. Office of Prevention, Pesticides and Toxic Substances (7505C). Pesticide Fact Sheet. Name of Chemical: Indoxacarb. Reason for Issuance: Conditional Registration. Date Issued: October 30, 2000. ] {{webarchive |url=https://web.archive.org/web/20040502142848/http://www.epa.gov/opprd001/factsheets/indoxacarb.pdf |date=May 2, 2004 }}[https://archive.today/20120803095707/http://www.epa.gov/EPA-PEST/2007/July/Day-11/p13339.htm United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132) ][http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2006:025:0024:0027:EN:PDF Commission Directive 2006/10/EC of 27 January 2006 amending Council Directive 91/414/EEC to include forchlorfenuron and indoxacarb as active substances. Official Journal of the European Union 2006-1-28]
Its main mode of action is via blocking of neuronal sodium channels, belonging to IRAC group 22A. It is fairly lipophilic with a Kow of 4.65. This pesticide should be used with caution since some insects such as the oriental tobacco budworm (Helicoverpa assulta) become resistant when exposed.{{Cite journal|last1=Wang|first1=Kai-Yun|last2=Zhang|first2=Yong|last3=Wang|first3=Hong-Yan|last4=Xia|first4=Xiao-Ming|last5=Liu|first5=Tong-Xian|date=2010-01-01|title=Influence of three diets on susceptibility of selected insecticides and activities of detoxification esterases of Helicoverpa assulta (Lepidoptera: Noctuidae)|journal=Pesticide Biochemistry and Physiology|volume=96|issue=1|pages=51–55|doi=10.1016/j.pestbp.2009.09.003|bibcode=2010PBioP..96...51W }}
In 2021, the European Union{{cite web | url=https://op.europa.eu/en/publication-detail/-/publication/6316d2fd-50b7-11ec-91ac-01aa75ed71a1/language-en | title=C/2021/8467, Commission Implementing Regulation (EU) 2021/2081 of 26 November 2021 concerning the non-renewal of approval of the active substance indoxacarb, in accordance with Regulation (EC) No 1107/2009 of the European Parliament and of the Council concerning the placing of plant protection products on the market, and amending Commission Implementing Regulation (EU) No 540/2011 (Text with EEA relevance) | date=26 November 2021 }} chose not to renew Indoxacarb for use as a plant-protection insecticide. The United Kingdom still allows use of the compound until 2025.{{cite web | url=https://www.hse.gov.uk/biocides/uk-authorised-biocidal-products.htm | title=UK authorised biocidal products - Biocides - HSE }}
Development
Indoxacarb was developed by the McCann et al. team at E. I. du Pont de Nemours.{{cite journal | last1=McCann | first1=Stephen F | last2=Annis | first2=Gary D | last3=Shapiro | first3=Rafael | last4=Piotrowski | first4=David W | last5=Lahm | first5=George P | last6=Long | first6=Jeffery K | last7=Lee | first7=Kevin C | last8=Hughes | first8=Margaret M | last9=Myers | first9=Brian J | last10=Griswold | first10=Sandra M | last11=Reeves | first11=Bonita M | last12=March | first12=Robert W | last13=Sharpe | first13=Paula L | last14=Lowder | first14=Patrick | last15=Barnette | first15=William E | last16=Wing | first16=Keith D | title=The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides | journal=Pest Management Science | publisher=Society of Chemical Industry (Wiley) | volume=57 | issue=2 | year=2001 | issn=1526-498X | doi=10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o | pages=153–164 | pmid=11455646}}{{cite book | last1=McCann | first1=Stephen F. | last2=Annis | first2=Gary D. | last3=Shapiro | first3=Rafael | last4=Piotrowski | first4=David W. | last5=Lahm | first5=George P. | last6=Long | first6=Jeffrey K. | last7=Lee | first7=Kevin C. | last8=Hughes | first8=Margaret M. | last9=Myers | first9=Brian J. | last10=Griswold | first10=Sandra M. | last11=Reeves | first11=Bonita M. | last12=March | first12=Robert W. | last13=Sharpe | first13=Paula L. | last14=Lowder | first14=Patrick | last15=Tseng | first15=Paul | last16=Barnette | first16=William E. | last17=Wing | first17=Keith D. | volume=800 | title=Synthesis and Chemistry of Agrochemicals VI | series=ACS Symposium Series | chapter=Synthesis and Biological Activity of Oxadiazine and Triazine Insecticides: The Discovery of Indoxacarb | publisher=American Chemical Society | publication-place=Washington, DC | date=2001-07-23 | issn=0097-6156 | doi=10.1021/bk-2002-0800.ch016 | pages=166–177| isbn=9780841237834 }}
Household products
Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion.{{cite web
|url = http://www.scientificblogging.com/news_releases/indoxacarb_insecticide_wipes_out_entire_cockroach_generations
|archive-url = https://web.archive.org/web/20080627103446/http://www.scientificblogging.com/news_releases/indoxacarb_insecticide_wipes_out_entire_cockroach_generations
|url-status = live
|archive-date = June 27, 2008
|title = Indoxacarb Insecticide Wipes Out Entire Cockroach Generations
|access-date = 2009-12-14
|date = June 23, 2008
}}
In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.{{Cite web | url=https://www.syngenta-us.com/newsroom/news_release_detail?id=169537 | title = Syngenta Acquires DuPont Professional Products Insecticide Business | website = syngenta-us.com }}
Indoxacarb is the active ingredient in the pet product, Activyl, from Merck Animal Health. It is marketed to kill fleas on dogs and cats.{{cite web | url = https://www.merck-animal-health-usa.com/activyl | title = Activyl | website = merck-animal-health-usa.com }}
Toxicity to humans
While toxicity to humans has not been formally studied, there is a reported case of a person consuming indoxacarb in a suicide attempt.{{Cite journal|last1=Prasanna|first1=Lakshmi|last2=Rao|first2=S. Manimala|last3=Singh|first3=Vishal|last4=Kujur|first4=Rash|last5=Gowrishankar|date=2008|title=Indoxacarb poisoning: An unusual presentation as methemoglobinemia|journal=Indian Journal of Critical Care Medicine |volume=12|issue=4|pages=198–200|doi=10.4103/0972-5229.45082|issn=0972-5229|pmc=2738321|pmid=19742262 |doi-access=free }} The patient developed methemoglobinemia following ingestion. Methemoglobinemia (also known as blue baby syndrome) is a condition which ultimately decreases the effectiveness of red blood cells to exchange oxygen with organs. Methemoglobinemia can be fatal if left untreated, however when the cause is exposure to a chemical agent (not genetic) a variety of treatments are available and effective.{{Cite journal |last=Rehman |first=Habib Ur |date=September 2001 |title=Methemoglobinemia |journal=The Western Journal of Medicine |volume=175 |issue=3 |pages=193–196 |doi=10.1136/ewjm.175.3.193 |pmid=11527852 |pmc=1071541 }}{{Citation |last1=Ludlow |first1=John T. |title=Methemoglobinemia |date=2023 |url=http://www.ncbi.nlm.nih.gov/books/NBK537317/ |work=StatPearls |access-date=2023-09-01 |place=Treasure Island (FL) |publisher=StatPearls Publishing |pmid=30726002 |last2=Wilkerson |first2=Richard G. |last3=Nappe |first3=Thomas M.}}
References
{{Reflist}}
Further reading
- {{cite journal
| last = Lapied
| first = Bruno
|author2=Françoise Grolleau |author3=David B Sattelle
| date= January 2001
| title = Indoxacarb, an oxadiazine insecticide, blocks insect neuronal sodium channels
| journal = Br J Pharmacol
| volume = 132
| issue = 2
| pages = 587–595
| pmid = 11159709
| doi = 10.1038/sj.bjp.0703853
| pmc = 1572588
}}
- {{cite journal
| last = Khambay
| first = Bhupinder P.S.
| year = 2002
| title = Pyrethroid Insecticides
| journal = Pesticide Outlook
| volume = 13
| issue =2
| pages = 49–54
| doi = 10.1039/b202996k
}}
- [http://www.cdpr.ca.gov/docs/emon/pubs/fatememo/indoxacarb.pdf Moncada, Adriana. Environmental Fate of Indoxacarb. Environmental Monitoring Branch, Department of Pesticide Regulation, State of California. March 6, 2003]
- {{cite journal| last =Tillman| first =P Glynn| author2 =Hammes, Glenn G| author3 =Sacher, Matthew| author4 =Connair, Michael| author5 =Brady, E Angela| author6 =Wing, Keith D| date =January 2002| title =Toxicity of a formulation of the insecticide indoxacarb to the tarnished plant bug, Lygus lineolaris (Hemiptera: Miridae), and the big-eyed bug, Geocoris punctipes (Hemiptera: Lygaeidae)| journal =Pest Manag. Sci.| volume =58| issue =1| pages =92–100| pmid =11838290| doi =10.1002/ps.426| url =http://grande.nal.usda.gov/ibids/index.php?mode2=detail&origin=ibids_references&therow=701948| url-status =dead| archive-url =https://web.archive.org/web/20080807031224/http://grande.nal.usda.gov/ibids/index.php?mode2=detail| archive-date =2008-08-07}}
External links
- [http://www2.dupont.com/Production_Agriculture/en_US/products_services/insecticides/Steward_FAQs.html DuPont Steward insecticide - FAQs. Updated 20 January 2007.] {{Webarchive|url=https://web.archive.org/web/20080821200702/http://www2.dupont.com/Production_Agriculture/en_US/products_services/insecticides/Steward_FAQs.html |date=21 August 2008 }} Retrieved 2012-11-11
- {{PPDB|399}}
{{insecticides}}
Category:Trifluoromethyl ethers