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Indoxacarb

Indoxacarb structure

Indoxacarb 

structure
  • CAS No:

    173584-44-6

  • Formula:

    C22H17ClF3N3O7

  • Chemical Name:

    Indoxacarb

  • Synonyms:

    Indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid,7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]-,methyl ester,(4aS)-;Indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid,7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-(trifluoromethoxy)phenyl]amino]carbonyl]-,methyl ester,(S)-;DPX-KN 128;Indoxacarb;Steward;(S)-Indoxacarb;Explicit;Avatar;KN 128;Avaunt;Indoxacarb MP;DPX-MP 062-381;DPX-MP 062-382;DPX-MP 062-390;DPX-MP 062-391;Parkway Mole Cricket Bait;DPX-MP 062-385;DPX-MP 062-400;Advion fire ant bait;Advion;Provaunt;Avaunt 30WG;Steward Gold;Steward EC;Activyl;Avaunt 30WDG;S-(+)-Indoxacarb;Steward 30WG;174060-41-4

  • Categories:

    Organic Chemistry  >  Carboxylic Acids and Derivatives

Description

Indoxacarb is an organochlorine insecticide and a methyl ester. It has a role as a voltage-gated sodium channel blocker.

Indoxacarb Basic Attributes

52783

527.83

605-683-4

52H0D26MWR

DTXSID1032690

White powder

QP53AC54|QP53AX27

Characteristics

107

4.65

1.44 g/cu cm at 20 deg C

88.1 deg C

571.4±60.0 °C at 760 mmHg

299.3±32.9 °C

1.602

In water, 0.20 mg/L at 20 deg C

0-6°C

1.9X10-10 mm Hg at 25 deg C

Henry's Law constant = 6.6X10-10 atm-cu m/mol at 25 °C /Estimated/

207.03 Ų [M+H]+ [CCS Type: TW]|205.99 Ų [M+H]+

Hydroxyl radical reaction rate constant = 4.2X10-11 cu cm/molecule sec at 25 °C /Estimated/

Safety Information

P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P314, P321, P330, P333+P313, P363, P391, P405, P501

H301

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

|Danger|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P314, P321, P330, P333+P313, P363, P391, P405, and P501|Aggregated GHS information provided by 211 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H301: Toxic if swallowed [Danger Acute toxicity, oral]|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P391, P403+P233, P405, and P501

Approved respirator. chemical resistant footwear plus socks. Long-sleeved shirts and long pants. Waterproof gloves.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|The protective clothing should be kept in separate places where it cannot be contaminated with toxic chemicals. It should be forbidden to keep this clothing in living quarters. Protective clothing must be washed at least once a week and each time it is contaminated with pesticides. Before washing the clothing should be soaked for several hours in a calcium carbonate solution. /Pesticides/|Smoking, eating, and drinking before washing should be absolutely prohibited when any pesticide ... is being handled or used. /Pesticides/

Toxicity

LD50 Rat (male) oral 1732 mg/kg /DPX-MP062, 3:1 mixture of (S) and (R) isomers/|LD50 Rat (female) oral 268 mg/kg /DPX-MP062, 3:1 mixture of (S) and (R) isomers/|LD50 Rabbit percutaneous >5000 mg/kg /DPX-MP062, 3:1 mixture of (S) and (R) isomers/

Indoxacarb's production may result in its release to the environment through various waste streams; it's use as an insecticide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8,100(SRC), determined from a log Kow of 4.65(2) and a regression-derived equation(3), indicates that indoxacarb is expected to be immobile in soil(SRC). Volatilization of indoxacarb from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.6X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 1.9X10-10 mm Hg(2), and water solubility, 0.20 mg/L(2). Indoxacarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Biodegradation data were not available(SRC, 2005).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8,100(SRC), determined from a log Kow of 4.65(2) and a regression-derived equation(3), indicates that indoxacarb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.6X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 1.9X10-10 mm Hg(2), and water solubility, 0.20 mg/L(2). According to a classification scheme(4), an estimated BCF of 2,000(SRC), from an estimated log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is very high(SRC). Aqueous hydrolysis half-lives measured for indoxacarb were greater than 30 days at pH 5, 38 days at pH 7, and 1 day at pH 9(2). Biodegradation data were not available(SRC, 2005).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), indoxacarb, which has a vapor pressure of 1.9X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase indoxacarb may be removed from the air by wet and dry deposition(SRC).

Aqueous hydrolysis half-lives measured for indoxacarb were greater than 30 days at pH 5, 38 days at pH 7, and 1 day at pH 9(1). Indoxacarb is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

An estimated BCF of 2,000 was calculated for indoxacarb(SRC), using an estimated log Kow of 4.65(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC), provided the compound is not altered physically or chemically once released into the environment.

The Koc of indoxacarb is estimated as 8,100(SRC), using a log Kow of 4.65(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that indoxacarb is expected to be immobile in soil.

The Henry's Law constant for indoxacarb is estimated as 6.6X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.9X10-10 mm Hg(1), and water solubility, 0.20 mg/L(1). This Henry's Law constant indicates that indoxacarb is expected to be essentially nonvolatile from moist soil or water surfaces(2). Indoxacarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

Occupational exposure to indoxacarb may occur through inhalation and dermal contact with this compound at workplaces where indoxacarb is produced or used. Occupational exposure to this substance may also occur during loading and application(1). The general population may be exposed to indoxacarb through contact with crops that have been treated with this insecticide(1). The general population may also be exposed to indoxacarb via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing indoxacarb(SRC).

Drug Information

Treatment of flea infestations (Ctenocephalides felis); the product has persistent insecticidal efficacy for up to 4 weeks against Ctenocephalides felis. The product has persistent acaricidal efficacy for up to 5 weeks against Ixodes ricinus and up to 3 weeks against Rhipicephalus sanguineus. One treatment provides repellent (anti-feeding) activity against sand flies (Phlebotomus perniciosus) for up to 3 weeks.|Treatment and prevention of flea infestation.For dogs and cats: Treatment and prevention of flea infestation.The veterinary medicinal product can be used as part of a treatment strategy for flea-allergy dermatitis. Developing stages of fleas in the pet's immediate surroundings are killed following contact with Activyl-treated pets.

Metabolism in rats after oral dosing was studied using both DPX-JW062 and DPX-MP062. Most of the dose was excreted within 96 hr. Extensive metabolism to numerous minor metabolites occurs. In urine, metabolites were cleaved products (indane or trifluoromethoxyphenyl ring products), whilst in feces, major metabolites retained both these moieties. Major metabolic reactions included hydroxylation of the indane ring, hydrolysis of the carboxymethyl group from the amino nitrogen, and opening of the oxadiazine ring, which gave rise to cleaved products.

... Indoxacarb inhibits sodium channels and certain subtypes of nicotinic receptors.|The effects of the oxadiazine insecticide indoxacarb and its N-decarbomethoxylated metabolite (DCJW) on tetrodotoxin-resistant (TTX-R) voltage-gated sodium channels in rat dorsal ganglion neurons were studied using the whole-cell patch clamp technique. Indoxacarb and DCJW suppressed the peak amplitude of action potentials, and DCJW exhibited a faster time course and higher potency than indoxacarb in the blocking effects. In voltage-clamp experiments, indoxacarb and DCJW suppressed TTX-R sodium currents in a time-dependent manner without a steady-state level of suppression. IC50 values for indoxacarb and DCJW on TTX-R sodium currents were estimated to be 10.7 and 0.8 microM after 25 min of bath application, respectively. DCJW was about 10 times more potent than indoxacarb in blocking TTX-R sodium currents. Although the suppressive effects of indoxacarb were partially reversible after washout with drug-free external solution, no recovery of sodium current was observed in DCJW treated neurons after prolonged washout. In current-voltage relationships, both indoxacarb and DCJW blocked the sodium currents to the same degree in the entire range of membrane potentials. The sodium conductance-voltage curve was not shifted along the voltage axis by indoxacarb and DCJW at 10 microM. In contrast, the steady-state inactivation curves were shifted in the hyperpolarizing direction by indoxacarb as well as by DCJW. Based on these results, it was concluded that indoxacarb and DCJW potently blocked the TTX-R sodium channel in rat DRG neurons with hyperpolarizing shifts of the steady-state inactivation curves, suggesting preferential association of the insecticides to the inactivated state of sodium channels. The small structural variation between indoxacarb and DCJW resulted in clear differences in potency for blocking sodium channels and reversibility after washout.

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

DPX-MP062

Indoxacarb Use and Manufacturing

Methods of Manufacturing

Preparation: G.D. Annis et al, WO 92 11249 (1992 to DuPont); eidem, US 5462938 (1995)

Uses

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

Dispersible granule; suspension concentrate.|DPX-JW062 is a 1:1 mixture of the (active) (S)- and (inactive) (R)- isomers; DPX-MP062 is a 3:1 mixture of these isomers. The pure (S)- isomer is referred to as DPX-KN128, the (R)- isomer as DPX-KN127.|Trade names: Avaunt, Steward, Avatar, Rumo, Tornado

Agrochemicals -> Insecticides|Veterinary drugs -> Activyl Tick Plus -> EMA Drug Category|permethrin, combinations, Ectoparasiticides for topical use, incl. insecticides -> Veterinary pharmacotherapeutic group|Veterinary drugs -> Activyl -> EMA Drug Category|Ectoparasiticides for topical use, incl. insecticides, indoxacarb -> Veterinary pharmacotherapeutic group|Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Indoxacarb has known environmental transformation products that include (4-trifluoromethoxy)phenyl urea, (E)-methyl 5-chloro-2,3-dihydro-2-hydroxy-1-((((methoxycarbonyl)(4-trifluoromethoxy)phenyl)amino)carbonyl)hydrazono)-1H-indene-2-carboxylate, and methyl-7-chloro-2,5-dihydro-2-(((trifluoromethoxy)phenyl)amino)carbonyl(indeno(1,3,4)oxadiazine-4a(3H)-carboxylate.|Indoxacarb has known environmental transformation products that include (4-trifluoromethoxy)phenyl urea, (E)-methyl 5-chloro-2,3-dihydro-2-hydroxy-1-((((methoxycarbonyl)(4-trifluoromethoxy)phenyl)amino)carbonyl)hydrazono)-1H-indene-2-carboxylate, and methyl-7-chloro-2,5-dihydro-2-[[[trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,3,4]oxadiazine-4a(3H)-carboxylate.

Computed Properties

Molecular Weight:527.8
XLogP3:4.8
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:5
Exact Mass:527.0707121
Monoisotopic Mass:527.0707121
Topological Polar Surface Area:107
Heavy Atom Count:36
Complexity:912
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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