Indoxacarb
Chemical compound
From Wikipedia, the free encyclopedia
Indoxacarb is an oxadiazine pesticide developed by DuPont that acts against lepidopteran larvae.[1] 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.[2][3][4]
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| 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) |
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| Abbreviations | DPX-MP062 |
| 8366683 | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.132.370 |
| KEGG | |
| MeSH | Indoxacarb |
PubChem CID |
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| UNII | |
| UN number | UN 3077 |
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) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Its main mode of action is via blocking of neuronal sodium channels, belonging to IRAC group 22A.[1] 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.[5]
In 2021, the European Union[6] chose not to renew Indoxacarb for use as a plant-protection insecticide. The United Kingdom still allows use of the compound until 2025.[7]
Development
Indoxacarb was developed by the McCann et al. team at E. I. du Pont de Nemours.[8][9]
Household products
Indoxacarb is the active ingredient in a number of household insecticides, including cockroach and ant baits, and can remain active after digestion.[10] In 2012 DuPont's Professional Products including the line of Advion and Arilon products was purchased by Syngenta.[11] Indoxacarb is the active ingredient in the pet product, Activyl, from Merck Animal Health. It is marketed to kill fleas on dogs and cats.[12]
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.[13] The patient developed methemoglobinemia 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]