Indoxacarb

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 Syngenta line of commercial pesticides: Advion and Arilon.[1][2][3]

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
  • 173584-44-6 Y
3D model (JSmol)
Abbreviations DPX-MP062
8366683
ChEBI
ChemSpider
ECHA InfoCard 100.132.370
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(CC3=C(C=CC(Cl)=C3)C2=N1)C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1
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).
Infobox references

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]

Household products

Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion.[5] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.[6] 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.[7]

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.[8] The patient developed methemoglobinemia following ingestion.[8] 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. "Indoxacarb Insecticide Wipes Out Entire Cockroach Generations". June 23, 2008. Archived from the original on June 27, 2008. Retrieved 2009-12-14.
  6. "Home".
  7. http://us.activyl.com
  8. 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.

Further reading
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