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Indoxacarb

From Wikipedia, the free encyclopedia
Indoxacarb
Stereo wireframe model of (4aS)-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)
AbbreviationsDPX-MP062
8366683
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.132.370Edit this at Wikidata
KEGG
MeSHIndoxacarb
UNII
UN numberUN 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 mass527.84 g·mol−1
Melting point88.1 °C (190.6 °F; 361.2 K) 99% indoxacarb PAI
Pharmacology
QP53AX27 (WHO)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Indoxacarb is anoxadiazinepesticide developed byDuPont that acts againstlepidopteran larvae.[1] It is marketed under the namesIndoxacarb Technical Insecticide,Steward Insecticide andAvaunt Insecticide. It is also used as the active ingredient in theSyngenta line of commercial pesticides:Advion andArilon.[2][3][4]

Its main mode of action isvia blocking of neuronal sodium channels, belonging toIRAC group 22A.[1] It is fairlylipophilic with aKow of 4.65. This pesticide should be used with caution since some insects such as theoriental tobacco budworm (Helicoverpa assulta) become resistant when exposed.[5]

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

Development

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

Household products

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Indoxacarb is the active ingredient in a number of householdinsecticides, includingcockroach andant baits, and can remain active after digestion.[10]In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased bySyngenta.[11]Indoxacarb is the active ingredient in the pet product, Activyl, fromMerck Animal Health. It is marketed to killfleas on dogs and cats.[12]

Toxicity to humans

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While toxicity to humans has not been formally studied, there is a reported case of a person consuming indoxacarb in asuicide attempt.[13] The patient developedmethemoglobinemia 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

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  1. ^abJeschke, 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.
  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 theWayback 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. Retrieved2009-12-14.
  11. ^"Syngenta Acquires DuPont Professional Products Insecticide Business".syngenta-us.com.
  12. ^"Activyl".merck-animal-health-usa.com. Archived fromthe original on 2024-01-11. Retrieved2024-01-11.
  13. ^abPrasanna, 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, retrieved2023-09-01

Further reading

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External links

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Carbamates
Inorganic compounds
Insect growth regulators
Neonicotinoids
Organochlorides
Organophosphorus
Pyrethroids
Diamides
Other chemicals
Metabolites
Biopesticides
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