Jump to content

Indoxacarb

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Citation bot (talk | contribs) at 01:08, 24 September 2022 (Add: title. Changed bare reference to CS1/2. | Use this bot. Report bugs. | Suggested by BrownHairedGirl | #UCB_webform 104/250). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Indoxacarb
Stereo wireframe model of (4aS)-Indoxacarb
Names
Preferred IUPAC name
Methyl 7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate
Systematic IUPAC name
(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
Identifiers
3D model (JSmol)
Abbreviations DPX-MP062
8366683
ChEBI
ChemSpider
ECHA InfoCard 100.132.370 Edit this at Wikidata
KEGG
MeSH Indoxacarb
UNII
UN number UN 3077
  • 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
    Key: VBCVPMMZEGZULK-UHFFFAOYSA-N
  • COC(=O)N(C(=O)N1COC2(C(=O)OC)Cc3cc(Cl)ccc3C2=N1)c1ccc(OC(F)(F)F)cc1
Properties
C22H17ClF3N3O7
Molar mass 527.84 g·mol−1
Melting point 88.1 °C (190.6 °F; 361.2 K) 99% indoxacarb PAI
Pharmacology
QP53AX27 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae. 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.[1][2][3]

Its main mode of action is via blocking of neuronal sodium channels. 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.[4]

The European Union [5] and United Kingdom [6] both banned it in 2022, on the ground, in the UK case, of "unacceptable risk to operators, workers, resident, and bystanders from the representative uses".

Development

Indoxacarb was developed by the McCann et al team at E. I. du Pont de Nemours.[7][8]

Household products

Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion.[9] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.[10] Indoxacarb is the active ingredient in the new pet product, Activyl from Merck Animal Health. It is marketed to kill fleas on dogs and cats.[11]

Toxicity to humans

While toxicity to humans has not been formally studied, there has been a report of a person trying to consume indoxacarb in a suicide attempt.[12] The patient developed methemoglobinemia following ingestion.[12] Methemoglobinemia is a condition which ultimately decreases the effectiveness of red blood cells to exchange oxygen with organs. Methemoglobinemia can be fatal if left untreated, but proper treatment of this condition can rapidly begin reversing it.

References

  1. ^ 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. Archived May 2, 2004, at the Wayback Machine
  2. ^ United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132)
  3. ^ 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
  4. ^ Wang, Kai-Yun; Zhang, Yong; Wang, Hong-Yan; Xia, Xiao-Ming; Liu, Tong-Xian (2010-01-01). "Influence of three diets on susceptibility of selected insecticides and activities of detoxification esterases of Helicoverpa assulta (Lepidoptera: Noctuidae)". Pesticide Biochemistry and Physiology. 96 (1): 51–55. doi:10.1016/j.pestbp.2009.09.003.
  5. ^ ]https://www.lab-sl.com/en/eu-bans-the-use-of-the-active-substance-indoxacarb-normally-used-as-a-pesticide-insecticide/]
  6. ^ "HSE to withdraw authorisation for use of indoxacarb pesticide".
  7. ^ McCann, Stephen F; Annis, Gary D; Shapiro, Rafael; Piotrowski, David W; Lahm, George P; Long, Jeffery K; Lee, Kevin C; Hughes, Margaret M; Myers, Brian J; Griswold, Sandra M; Reeves, Bonita M; March, Robert W; Sharpe, Paula L; Lowder, Patrick; Barnette, William E; Wing, Keith D (2001). "The discovery of indoxacarb: oxadiazines as a new class of pyrazoline-type insecticides". Pest Management Science. 57 (2). Society of Chemical Industry (Wiley): 153–164. doi:10.1002/1526-4998(200102)57:2<153::aid-ps288>3.0.co;2-o. ISSN 1526-498X. PMID 11455646.
  8. ^ McCann, Stephen F.; Annis, Gary D.; Shapiro, Rafael; Piotrowski, David W.; Lahm, George P.; Long, Jeffrey K.; Lee, Kevin C.; Hughes, Margaret M.; Myers, Brian J.; Griswold, Sandra M.; Reeves, Bonita M.; March, Robert W.; Sharpe, Paula L.; Lowder, Patrick; Tseng, Paul; Barnette, William E.; Wing, Keith D. (2001-07-23). "Synthesis and Biological Activity of Oxadiazine and Triazine Insecticides: The Discovery of Indoxacarb". Synthesis and Chemistry of Agrochemicals VI. ACS Symposium Series. Vol. 800. Washington, DC: American Chemical Society. pp. 166–177. doi:10.1021/bk-2002-0800.ch016. ISBN 9780841237834. ISSN 0097-6156.
  9. ^ "Indoxacarb Insecticide Wipes Out Entire Cockroach Generations". June 23, 2008. Archived from the original on June 27, 2008. Retrieved 2009-12-14.
  10. ^ "Home".
  11. ^ http://us.activyl.com
  12. ^ a b Prasanna, Lakshmi; Rao, S. Manimala; Singh, Vishal; Kujur, Rash; Gowrishankar (2008). "Indoxacarb poisoning: An unusual presentation as methemoglobinemia". Indian Journal of Critical Care Medicine. 12 (4): 198–200. doi:10.4103/0972-5229.45082. ISSN 0972-5229. PMC 2738321. PMID 19742262.{{cite journal}}: CS1 maint: unflagged free DOI (link)

Further reading

Retrieved from "https://en.wikipedia.org/w/index.php?title=Indoxacarb&oldid=1111978412"