Indoxacarb

• CAS: 173584-44-6
• Catalog Number: ACM173584446
• Category: Main Products
• Molecular Weight: 527.83
• Molecular Formula: C₂₂H₁₇ClF₃N₃O₇
• Synonyms: methyl (S)-N-[7-chloro-2,3,4a,5-tetrahydro-4a-(methoxycarbonyl)indeno[1,2-e][1,3,4]oxadiazin-2-ylcarbonyl]-4'-(trifluoromethoxy)carbanilate; INDOXACARB; methyl (S)-7-chloro-2,3,4a,5-tetrahydro-2-[methoxycarbonyl(4-trifluoromethoxyphenyl)carbamoyl]indeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate; methyl (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate; carb
• IUPAC Name: methyl(4aS)-7-chloro-2-[methoxycarbonyl-[4-(trifluoromethoxy)phenyl]carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate
• SMILES: COC(=O)C12CC3=C(C1=NN(CO2)C(=O)N(C4=CC=C(C=C4)OC(F)(F)F)C(=O)OC)C=CC(=C3)Cl
• InChI Key: VBCVPMMZEGZULK-NRFANRHFSA-N
• Boiling Point: 571.4ºC at 760 mmHg
• Melting Point: 88.1ºC
• Flash Point: 299.3ºC
• Density: 1.53g/cm³
• EC Number: 605-683-4
• Exact Mass: 527.07100

Case Study

Indoxacarb-Based Deep Eutectic Solvent System for Enhanced Lethal Activity Against Red Imported Fire Ants

Fu J, et al. Ecotoxicology and Environmental Safety, 2025, 289, 117709.

Indoxacarb (IDC) was formulated into deep eutectic solvents (DESs) with three fatty acids-oleic acid (OA), linoleic acid (LA), and linolenic acid (LNA)-to develop a DES-CaCO3 system with enhanced insecticidal effects against red imported fire ants (RIFAs). The DESs, prepared by combining IDC and fatty acids in a 1:1 molar ratio under vacuum and controlled heating conditions, demonstrated significantly improved lethal activity compared to IDC alone. Further screening of eutectic solvent ratios (1:2, 1:3, and 1:5) confirmed optimal stability and dispersibility for a 1:1 mixture.
To address water insolubility, green emulsifiers were incorporated to improve dispersion, enabling efficient coating applications. The DES-CaCO3 nanoparticles were synthesized via interfacial precipitation, involving the reaction of the emulsified DESs in calcium chloride and sodium carbonate solutions. The resulting OA@IDC@CaCO3, LA@IDC@CaCO3, and LNA@IDC@CaCO3 systems exhibited improved bioavailability and stability, effectively regulating RIFA behavior and achieving superior contact and feeding-based insecticidal activity.

A study on the environmental impacts of indolecarb

Wing, Keith D., et al. Crop Protection 19.8-10 (2000): 537-545.

Indolecarb is a non-systemic insecticide used to control sucking insects. Its insecticidal activity occurs by blocking sodium channels in the insect's nervous system, with entry via the stomach and contact routes. Results include impaired neurological function, cessation of feeding, paralysis, and death. Indolecarb is primarily used in agriculture. Indolecarb is relatively nonvolatile, with a low vapor pressure and a low Henry's law constant. Therefore, volatilization is not a significant factor in its dissipation. Its low water solubility, high Kow, and moderately high Koc indicate that indolecarb has a moderate to strong tendency to partition into soils, resulting in its relative immobility in soil. In vegetation, indolecarb appears to have no adverse effects on non-target terrestrial plants. Indolecarb is moderately to very toxic to freshwater, estuarine/marine fish, and insects. It is highly toxic to bees by contact, but is less toxic after application to vegetation after drying.
Indocarb is moderately hydrophobic, with a low water solubility of 0.2 mg/L and a log Kow of 4.6. This, combined with moderately high soil adsorption coefficients (Koc) of 2200 and 8200, indicates a relatively low potential for leaching into groundwater. In a soil column leaching study, radioactivity recoveries ranged from 82% to 95% within 15 cm. The lower 15-30 cm of the soil column contained <3% of the applied radioactivity. The glass column was eluted with at least 200 mm of 0.01 M CaCl2 over a 7-day period.

The effects of indolecarb on the multicolored Asian ladybird beetle

Galvan, T. L., R. L. Koch, and W. D. Hutchison. Biological control 34.1 (2005): 108-114.

The use of selective insecticides, such as spinosad and indolecarb, which are more toxic to lepidopteran pests than to Harmonia axyridis (Pallas), can promote the protection of this predator in integrated pest management (IPM) of sweet corn. The effects of spinosad and indolecarb on the survival, development, and reproduction of H. axyridis were examined by spraying last instar and adult females. The results showed that spinosad and indolecarb can reduce H. axyridis population growth by inhibiting its survival, development, and reproduction.
Treatments for the last instar assay included spinosad at 10%, 25%, and 50% wet rate (FR), indolecarb at 10% FR, and water. Survival of each life stage, time to adult development, and adult weight were recorded. Indolecarb reduced the survival of Wrst instars and adults, prolonged the development time of Wrst instar adults, and reduced the fecundity of female H. axyridis. Spinosad reduced the survival of Wrst instars, prolonged the time it took for Wrst instars to become adults, reduced weight gain, and reduced the fecundity of female H. axyridis.

Study on indolecarb to block sodium channels in insect neurons

Lapied, Bruno, Françoise Grolleau, and David B. Sattelle. British journal of pharmacology 132.2 (2001): 587-595.

Decarboxymethoxylated JW062 (DCJW), the active ingredient of the novel oxadiazine insecticide DPX-JW062 (indolecarb), was tested on action potentials and inward sodium currents recorded from short-term cultures of dorsal unpaired median neurons of the American cockroach. Based on IC values, DCJW was approximately 10-fold less potent than tetrodotoxin (TTX) but 1000-fold more potent than the local anesthetic lidocaine. DCJW (100 n) had no effect on the activation properties, reversal potential, voltage dependence of the sodium conductance, or fast and slow steady-state inactivation of the sodium current. Co-administration of lidocaine (IC30 m) with various concentrations of DCJW reduced its apparent potency, indicating that DCJW and lidocaine act at the same site. The extracellular solution used for recording inward sodium currents contained NaCl, tetraethylammonium chloride, KCl, calcium chloride, magnesium chloride, CdCl2, 4-aminopyridine, and HEPES, pH 7.4.
A 10 M stock solution of DCJW from indole was prepared in dimethyl sulfoxide (DMSO). Final dilutions contained a maximum of 0.1% DMSO. These solvent concentrations were found to have no effect on the electrical activity of DUM neurons. Experiments were performed at room temperature (20°C).

Custom Q&A

What is the molecular formula of indoxacarb?

The molecular formula of indoxacarb is C22H17ClF3N3O7.

What are some synonyms for indoxacarb?

Some synonyms for indoxacarb include Steward, Provaunt, Advion, Avaunt, and Avatar.

What is the chemical name for indoxacarb?

The chemical name for indoxacarb is methyl (4aS)-7-chloro-2-[methoxycarbonyl-(4-(trifluoromethoxy)phenyl)carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate.

Is indoxacarb an insecticide?

Yes, indoxacarb is an insecticide.

What is the structure of indoxacarb?

The structure of indoxacarb is shown in the provided images (Indoxacarb2d.png and Indoxacarb3d.png).

What is the CAS number of indoxacarb?

The CAS number of indoxacarb is 173584-44-6.

What is the role of indoxacarb?

Indoxacarb acts as a voltage-gated sodium channel blocker.

What are the health hazards associated with indoxacarb?

The reference mentions indoxacarb as an acute toxic, health hazard, and environmental hazard. However, specific details about health hazards are not provided.

What is the IUPAC name of indoxacarb?

The IUPAC name of indoxacarb is methyl (4aS)-7-chloro-2-[methoxycarbonyl-(4-(trifluoromethoxy)phenyl)carbamoyl]-3,5-dihydroindeno[1,2-e][1,3,4]oxadiazine-4a-carboxylate.

What is the UNII number of indoxacarb?

The UNII number of indoxacarb is 52H0D26MWR.