Indoxacarb

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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. 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

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]

In 2021, the European Union[5] chose not to renew Indoxacarb for use as an insecticide. The United Kingdom still allows use of the compound until 2025.[6]

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 pet product, Activyl, from

fleas on dogs and cats.[11]

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.[12] The patient developed methemoglobinemia following ingestion.[12] 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.[13][14]

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. doi:10.1016/j.pestbp.2009.09.003
    .
  5. ^ "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.
  6. ^ "UK authorised biocidal products - Biocides - HSE".
  7. PMID 11455646
    .
  8. 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. ^ "Syngenta Acquires DuPont Professional Products Insecticide Business". syngenta-us.com.
  11. ^ "Activyl". merck-animal-health-usa.com.
  12. ^
    PMID 19742262
    .
  13. PMID 11527852
    .
  14. PMID 30726002
    , retrieved 2023-09-01

Further reading

External links
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