Indoxacarb
Chemical compound / From Wikipedia, the free encyclopedia
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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.[1][2][3]
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 | |
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. 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.[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]