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'''Indoxacarb''' is an oxadiazine [[pesticide]] developed by [[DuPont]] that acts against [[lepidoptera]]n 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'''.<ref>[http://www.epa.gov/opprd001/factsheets/indoxacarb.pdf 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. ]{{Dead link|date=October 2015}}</ref><ref>[http://www.epa.gov/EPA-PEST/2007/July/Day-11/p13339.htm United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132) ]{{Dead link|date=October 2015}}</ref><ref>[http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2006:025:0024:0027:EN:PDF 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]</ref>
'''Indoxacarb''' is an oxadiazine [[pesticide]] developed by [[DuPont]] that acts against [[lepidoptera]]n 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'''.<ref>[http://www.epa.gov/opprd001/factsheets/indoxacarb.pdf 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. ] {{wayback|url=http://www.epa.gov/opprd001/factsheets/indoxacarb.pdf |date=20040502142848 }}</ref><ref>[http://www.epa.gov/EPA-PEST/2007/July/Day-11/p13339.htm United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132) ]{{Dead link|date=October 2015}}</ref><ref>[http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=OJ:L:2006:025:0024:0027:EN:PDF 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]</ref>


Its main mode of action is via blocking of nerve [[sodium channel]]s. It is fairly [[lipophilic]] with a [[dissociation constant|K<sub>ow</sub>]] of 4.65.
Its main mode of action is via blocking of nerve [[sodium channel]]s. It is fairly [[lipophilic]] with a [[dissociation constant|K<sub>ow</sub>]] of 4.65.

Revision as of 01:26, 22 January 2016

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(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).

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]

Its main mode of action is via blocking of nerve sodium channels. It is fairly lipophilic with a Kow of 4.65.

Household products

Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion. [4] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.[5] 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.[6]

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 2004-05-02 at the Wayback Machine
  2. ^ United States Environmental Protection Agency. Federal Register: Indoxacarb; Pesticide Tolerance. Federal Register: July 11, 2007 (Volume 72, Number 132) [dead link]
  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. ^ "Indoxacarb Insecticide Wipes Out Entire Cockroach Generations". June 23, 2008. Retrieved 2009-12-14.
  5. ^ http://www3.syngenta.com/country/au/en/news/releases/Pages/Syngenta-acquires-DuPont-Professional-Products.aspx
  6. ^ http://us.activyl.com

Further reading

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