Indoxacarb

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
ChEMBL
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.[1] 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.[2][3][4]

Its main mode of action is via blocking of neuronal sodium channels, belonging to IRAC group 22A.[1] 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.[5]

In 2021, the European Union[6] chose not to renew Indoxacarb for use as a plant-protection insecticide. The United Kingdom still allows use of the compound until 2025.[7]

Development

Indoxacarb was developed by the McCann et al. team at E. I. du Pont de Nemours.[8][9]

Household products

Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion.[10] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.[11] Indoxacarb is the active ingredient in the pet product, Activyl, from Merck Animal Health. It is marketed to kill fleas on dogs and cats.[12]

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.[13] The patient developed methemoglobinemia following ingestion.[13] 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.[14][15]

References

  1. ^ a b Jeschke, Peter; Witschel, Matthias; Krämer, Wolfgang; Schirmer, Ulrich (25 January 2019). "33.4 Voltage-dependent Sodium Channel-blocking Insecticides". Modern Crop Protection Compounds (3rd ed.). Wiley-VCH. pp. 1424–1448. doi:10.1002/9783527699261. ISBN 9783527699261.{{cite book}}: CS1 maint: date and year (link)
  2. ^ 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
  3. ^ United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132)
  4. ^ 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
  5. ^ 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. Bibcode:2010PBioP..96...51W. doi:10.1016/j.pestbp.2009.09.003.
  6. ^ "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)". 26 November 2021.
  7. ^ "UK authorised biocidal products - Biocides - HSE".
  8. ^ 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.
  9. ^ 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.
  10. ^ "Indoxacarb Insecticide Wipes Out Entire Cockroach Generations". June 23, 2008. Archived from the original on June 27, 2008. Retrieved 2009-12-14.
  11. ^ "Syngenta Acquires DuPont Professional Products Insecticide Business". syngenta-us.com.
  12. ^ "Activyl". merck-animal-health-usa.com.
  13. ^ 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.
  14. ^ Rehman, Habib Ur (September 2001). "Methemoglobinemia". The Western Journal of Medicine. 175 (3): 193–196. doi:10.1136/ewjm.175.3.193. PMC 1071541. PMID 11527852.
  15. ^ Ludlow, John T.; Wilkerson, Richard G.; Nappe, Thomas M. (2023), "Methemoglobinemia", StatPearls, Treasure Island (FL): StatPearls Publishing, PMID 30726002, retrieved 2023-09-01

Further reading