Methoxyfenozide

368.47

368.47

605-245-2

62A22651ZX

DTXSID3032628

White powder

29145090

58.6

3.7 (shake flask)

White powder

1.098±0.06 g/cm3(Predicted)

204.5 °C

530.3±60.0 °C at 760 mmHg

274.5±32.9 °C

1.539

In water, 3.3 mg/L at 20 deg C

0-6°C

3.5X10-11 mm Hg at 25 deg C (est)

LD50 in rats, mice (mg/kg): >5000, >5000 orally; in rats (mg/kg): >2000 dermally; LC50 in rats (mg/l): >4.3 by inhalation; LC50 (8 day dietary) in mallard duck, bobwhite quail (mg/kg diet): >5620, >5620; LC50 in bluegill sunfish, Daphnia magna (mg/l): >4.3 (96 hr); 3.7 (48 hr) (Le)

Henry's Law constant = 3.84X10-12 atm-cu m/mol at 25 °C (est)

UN 3077 9 / PGIII

2

51/53

60

N

P273, P391, P501

H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|Wastes resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. /Intrepid 2F Insecticide/|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

|Warning|H400 (31.3%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 230 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Not Classified

Applicators and other handlers must wear: Long-sleeved shirt and long pants. Chemical-resistant gloves made of any waterproof material. Shoes plus socks. /Intrepid 2F Insecticide/|... Restricted-entry interval (REI) of 4 hours. Personal protective equipment (PPE) required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water is: Coveralls, Chemical resistant gloves made of any waterproof material. Shoes plus socks. /Intrepid 2F Insecticide/

Remain upwind. Avoid breathing smoke. Use water spray to cool containers exposed to fire. Contain run-off. /Intrepid 2F Insecticide/|Wear positive-pressure, self-contained breathing apparatus and full protective clothing. Do not allow water from fire-fighting to enter water supplies. /Intrepid 2F Insecticide/|Use the following extinguishing media when fighting fires involving this material: carbon dioxide, dry chemical, water spray or foam. /Intrepid 2F Insecticide/

Pesticide particulates can become airborne. Dried product can burn. /Intrepid 2F Insecticide/

Contain and absorb small spills with inert materials with sand or earth. Transfer liquids and solid diking material to separate suitable containers for recovery or disposal. Avoid breathing vapor. Keep spills and cleaning run-off out of municipal sewers and open bodies of water. ... . If exposed to material during clean-up operations, remove all contaminated clothing promptly. Wash all exposed skin areas with soap and water immediately after exposure. Thoroughly lauder clothing before reuse. Do not take clothing home to be laundered. /Intrepid 2F Insecticide/|Do not contaminate water when cleaning equipment or disposing of equipment washwaters. /Intrepid 2F Insecticide/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Intrepid 2F Insecticide/|For terrestrial uses, do not apply directly to water or to areas where surface water is present or to intertidal areas below the mean high water mark. /Intrepid 2F Insecticide/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove contaminated clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Intrepid 2F Insecticide/|Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If not such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Intrepid 2F Insecticide/|For more Preventive Measures (Complete) data for Methoxyfenozide (7 total), please visit the HSDB record page.

LC50 Rat inhalation >4.3 mg/L/4 hr|LD50 Rat skin 2000 mg/kg|LD50 Rat oral 5000 mg/kg|LD50 Mouse oral 5000 mg/kg

Methoxyfenozide's production may result in its release to the environment through various waste streams; its 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 1,100(SRC), determined from a log Kow of 3.7(2) and a regression-derived equation(3), indicates that methoxyfenozide is expected to have low mobility in soil(SRC). Volatilization of methoxyfenozide from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Methoxyfenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2011).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.70(2) and a regression-derived equation(3), indicates that methoxyfenozide is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 3.8X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 130(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). Using natural lake water, an aqueous photolysis half-life range of 7 to 10 days has been reported(7). Biodegradation data in water were not available(SRC, 2011).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methoxyfenozide, which has an estimated vapor pressure of 3.5X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase. Particulate-phase methoxyfenozide may be removed from the air by wet or dry deposition(SRC). Methoxyfenozide contains chromophores that absorb at wavelengths >290 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Methoxyfenozide is stable to hydrolysis at pH 5, 7 and 9(1) and has been reported as relatively not important in the environment when compared to photolysis(2). Methoxyfenozide contains chromophores that absorb at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC). A photolytic half-life in pond water of 77 days has been reported(1). Photodecomposition in aqueous solutions (sterilized lake water from Guishui Lake, south of Beijing China) follows first-order kinetics under UV and natural sunlight. This slightly eutrophic lake is influenced by agricultural runoff(2). Half-lives of 10.85 minutes and 6.63-10.16 days, under UV (detection performed at 230 nm) and natural sunlight conditions (sunlight intensity at 300 to 400 nm), respectively, have been reported(2). Under UV degradation, two products were identified: N-t-butyl-N-(3,5-dimethylbenzoyl) and 3,7-dimethyl-benzoatedihydrofuran(2). A soil photolysis half-life has been reported as 173 days(1).

An estimated BCF of 130 was calculated in fish for methoxyfenozide(SRC), using a log Kow of 3.70(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not metabolized by the organism(SRC).

The Koc of methoxyfenozide is estimated as 1100(SRC), using a log Kow of 3.70(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that methoxyfenozide is expected to have low mobility in soil.

The Henry's Law constant for methoxyfenozide is estimated as 3.8X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that methoxyfenozide is expected to be essentially nonvolatile from water and moist soil surfaces(2). Methoxyfenozide is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.5X10-11 mm Hg(SRC), determined from a fragment constant method(3).

Occupational exposure to methoxyfenozide may occur through inhalation and dermal contact with this compound at workplaces where methoxyfenozide is produced or used. (SRC)

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

Forty two groups of Sprague Dawley rats (up to 5/sex/group) were dosed by oral gavage with either (14)C-t-butyl-, (14)C-A-Ring-, or (14)C-B-Ring-Methoxyfenozide at doses of 10 or 1000 mg/kg. Some treatments were performed by combining appropriate amount of non-labeled or (13)C-labeled Methoxyfenozide to the (14)C-Methoxyfenozide. Three types of experiments were performed: (1) determination of excretion, distribution, and mass balance 120 hours post dose; (2) pharmacokinetics in blood (Cmax and 1/2 Cmax); and (3) tissue distribution of (14)C at Cmax and 1/2 Cmax. The (14)C was mostly excreted during the first 24 hours with 58-77% of the administered dose recovered in the feces and 4-9% of the dose found in urine from day 0-1. The position of the carbon label did not alter the excretion profile significantly. Approximately, 0.07-0.23% of (14)C remained in the tissues, and 0.03-0.11% were recovered as (14)C-CO2 and volatile organics from day 0-5 post dose. The maximum concentrations of (14)C-Methoxyfenozide in the blood were observed at 15-30 minutes post dose for all three (14)C-labels. The highest tissue concentration of (14)C was in the liver. The (14)C residues were rapidly cleared from all organs in the rat. Based on the recovery of (14)C from the bile, urine, tissues and carcasses, 62-70% of the administered dose was systemically absorbed.|The tissue distribution of radioactivity was investigated after a single dose of A-ring-labelled or t-butyl-labelled methoxyfenozide administered by gavage (at Cmax, 1/2 Cmax and at 5 days after dosing at 10 or 1000 mg/kg bw), and after a single dose of B-ring-labelled methoxyfenozide (5 days after dosing at 10 mg/kg bw). Tissue distribution was also investigated after dosing with A-ring-labelled methoxyfenozide at 10 mg/kg bw as a pulse dose (5 days after dosing) and as a repeated dose (at 0.25 hr after the last dose, at about Cmax). Similar results were seen in all experiments. The absorbed radioactivity was widely distributed, with the highest concentration of absorbed radioactivity found in the liver at 0.5-2 hr after dosing (the higher concentrations found in the stomach and intestinal tract were attributed to largely unabsorbed material). ... Clearance from the body was extensive; 5 days after a single dose of 10 mg/kg bw, the highest percentage of radioactivity, representing <0.1% of the administered dose, was found in the liver.|The biliary excretion of radiolabel after a single oral dose of ((14)C-A-ring) methoxyfenozide at 10 mg/kg was investigated in bile-duct cannulated rats. Biliary excretion was rapid, with 22% (females) and 50% (males) of the administered dose being excreted within 12 hr. Overall, 38% (females) and 64% (males) of the radiolabel was excreted in bile within 72 hr. Considerable variability between individual animals was seen in cannulated female rats (bile, 13-55%; and urine, 5-43% within 72 hr), but the overall amount absorbed (in bile, urine, carcass and tissues) was similar for all four females (56-67%). Taking the biliary component into account, the overall extent of oral absorption of methoxyfenozide at a dose of 10 mg/kg bw was 60-70% in both sexes.|The dermal absorption in vivo of methoxyfenozide formulated as an aqueous flow-able liquid (RH-112,485 2F) or as a wettable powder (RH-112,485 280WP) was tested in rats in a study that was designed to comply with US EPA guidelines and GLP. The methoxyfenozide administered was uniformly labelled with (14)C on the methoxyphenyl ring; this is acceptable given the limited cleavage seen in studies of oral metabolism. To provide data on exposure to the concentrated product and in-use-dilutions, groups of four male Crl : CD BR rats received radiolabelled methoxyfenozide at three aqueous dilutions (0.025, 0.25, or 2.5% w/v), applied in a volume of 100 uL to a shaved area of about 10 sq cm for 1, 10, or 24 hr. Systemically absorbed methoxyfenozide was defined as the radiolabel found in the carcass, urine (plus urine funnel and cage washes), feces, and whole blood. For RH-112,485 2F, the total mean recovery of radiolabel in all groups ranged from 98% to 114%. After an exposure of 1, 10, or 24 hr to (14)C-labelled RH-112,485 2F formulation diluted in water to a concentration of 2.5, 0.25, or 0.025% w/v, a small amount of radiolabel (<1-4%) was systemically absorbed. For RH-112,485 280 WP, three animals with poor recoveries were excluded from further analysis. The total mean recovery of radiolabel in all groups ranged from 85% to 110%. After an exposure of 1, 10, or 24 hr to (14)C-labelled RH-112,485 280 WP at a concentration of 2.5, 0.25, or 0.025% w/v, <1-2% of radiolabel was systemically absorbed. Findings were similar for both formulations. The amount of radiolabel that was systemically absorbed did not increase linearly between the 10-hr and 24-hr exposure periods, indicating that most of the radiolabel that remained in or on the skin after washing was tightly bound and was not available for systemic absorption. This study shows that methoxyfenozide is poorly absorbed (<4%) after dermal exposure to either of the formulated products or in-use dilutions. The low rate of dermal absorption may be attributed to very low solubility in water (3.3 mg/L at 20 °C).

Forty two groups of Sprague Dawley rats (up to 5/sex/group) were dosed by oral gavage with either (14)C-t-butyl-, (14)C-A-Ring-, or (14)C-B-Ring-Methoxyfenozide at doses of 10 or 1000 mg/kg. ... (14)C- Methoxyfenozide was extensively metabolized into 32 metabolites (26 identified) isolated from urine and feces, and 24 metabolites were found and characterized from the bile. Seven metabolites comprised of 59-69% and 42-56% of the dose at 10 and 1000 mg/kg dose levels, respectively. Parent comprised of 14-26% and 30-39% of the administered (14)C at 10 and 1000 mg/kg dose levels, respectively.|Parent compound was found only in the feces (not in the urine or bile) and comprised 14-26% and 30-39% of the administered dose for animals at the lower and higher doses, respectively, indicating that animals at the lower dose metabolized a greater fraction of the administered dose compared with animals at the higher dose. Seven metabolites (M10, M14, M16, M22, M24, M28, M30) were found to be present in feces plus urine each at >2% of the administered dose. The predominant metabolites were M14 (desmethylated parent) and M24 (hydroxy methyl derivative). Parent compound plus these seven metabolites accounted for 74-90% of the administered dose (in feces plus urine) in all groups. For each of these groups, the total of parent plus identified metabolites accounted for >/= 83% of the administered dose, i.e. the metabolic profile of methoxyfenozide in feces and urine was well defined. Less than 5% of the administered dose was present as metabolites formed from the cleavage of the amide bridge.|Two metabolites, M16 (A-ring glucuronide of M14) and M26 (A-ring glucuronide of M24), were the main metabolites in bile. M16 was present at 13% and 18% in males and females respectively, M26 was present at 5% in males and 11% in females, all other metabolites represented <3% of the administered dose. The presence of M16 and M26 at higher concentrations in bile than in feces indicates that these two metabolites were subject to subsequent hydrolysis.|The primary /metabolic/ pathway probably involves demethylation of the A-ring methoxy moiety to form the corresponding phenol (M14), which is conjugated with glucuronic acid to form M16. Hydroxylation on the B-ring methyl moieties is also a significant metabolic pathway. Cleavage of methoxyfenozide to release either of the rings or the t-butyl group is only a minor pathway; none of the cleaved metabolites (M06, M07, M13, M32-36) were present at >2% of the dose. In males, however, cleaved metabolites represented up to about 50% of the metabolites found in urine. There was an indication that males cleaved more of the absorbed dose than did females, on the basis of urinary metabolite patterns.|Results for the animals receiving diets containing methoxyfenozide for 14 days plus a single dose of (14C) methoxyfenozide at 10 mg/kg bw by gavage showed evidence of induction of metabolism. Concentrations of M22, M28 and M30 increased, while concentrations of M14 and M24 were reduced relative to concentrations in animals that received only a single dose of (14C) methoxyfenozide at 10 mg/kg bw.

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). 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 0.9% saline (NS) 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 ... . /Poisons A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/

methoxyfenozide

Suspension concentrate, wettable powder.|Methoxyfenozide Technical (Dow Agrosciences, LLC) Methoxyfenozide 98.2%|Intrepid 80WSP Agricultural Insecticide (Dow Agrosciences, LLC) Methoxyfenozide 80%|Intrepid 2F Agricultural Insecticide (Dow Agrosciences, LLC) Methoxyfenozide 22.6%|Intrepid Mup (Dow Agrosciences, LLC) Methoxyfenozide 80%

The WHO Recommended Classification of Pesticides by Hazard identifies methoxyfenozide as unlikely to present an acute hazard in normal use; Main Use: insecticide.

Adequate analytical methodologies are available, e.g., high performance liquid chromatography with ultraviolet or mass spectrometry detection (HPLC/ UV or MS), for enforcing methoxyfenozide tolerances. Depending on the plant commodity, the limit of quantitation (LOQ) for methoxyfenozide in primary crop commodities is 0.01- 0.05 ppm.|Determination of residues in soil by HPLC/UV.

Agrochemicals -> Insecticides|Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Methoxyfenozide has known environmental transformation products that include Methoxyfenozide M08.