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| Names | |
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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 | |
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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 | |
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3D model (JSmol)
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| Abbreviations | DPX-MP062 |
| 8366683 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.132.370 |
| KEGG | |
| MeSH | Indoxacarb |
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PubChem CID
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| UNII | |
| UN number | UN 3077 |
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CompTox Dashboard (EPA)
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| 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) | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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.
In 2021, the European Union chose not to renew Indoxacarb for use as an insecticide. The United Kingdom still allows use of the compound until 2025.
Development
Indoxacarb was developed by the McCann et al team at E. I. du Pont de Nemours.
Household products
Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion. In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta. Indoxacarb is the active ingredient in the pet product, Activyl, from Merck Animal Health. It is marketed to kill fleas on dogs and cats.
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. The patient developed methemoglobinemia following ingestion. 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.
Further reading
- Lapied, Bruno; Françoise Grolleau; David B Sattelle (January 2001). "Indoxacarb, an oxadiazine insecticide, blocks insect neuronal sodium channels". Br J Pharmacol. 132 (2): 587–595. doi:10.1038/sj.bjp.0703853. PMC 1572588. PMID 11159709.
- Khambay, Bhupinder P.S. (2002). "Pyrethroid Insecticides". Pesticide Outlook. 13 (2): 49–54. doi:10.1039/b202996k.
- Moncada, Adriana. Environmental Fate of Indoxacarb. Environmental Monitoring Branch, Department of Pesticide Regulation, State of California. March 6, 2003
- Tillman, P Glynn; Hammes, Glenn G; Sacher, Matthew; Connair, Michael; Brady, E Angela; Wing, Keith D (January 2002). "Toxicity of a formulation of the insecticide indoxacarb to the tarnished plant bug, Lygus lineolaris (Hemiptera: Miridae), and the big-eyed bug, Geocoris punctipes (Hemiptera: Lygaeidae)". Pest Manag. Sci. 58 (1): 92–100. doi:10.1002/ps.426. PMID 11838290. Archived from the original on 2008-08-07.
External links
- DuPont Steward insecticide - FAQs. Updated 20 January 2007. Retrieved 2012-11-11
- Indoxacarb in the Pesticide Properties DataBase (PPDB)