Metofluthrin, trans-(E)-

360.13485714

DTXSID10158405

Pale yellow liquid

log Kow = 4.97-5.03 at 25 °C

1.21 at 20 °C

334 °C at atmospheric pressure

Solvent solubility (20 to 25 °C; g/L): acetone 303.4; methanol 312.2; ethyl acetate 307.6; toluene 326.9; n-hexanes 328.7; dichloromethane 318.9; n-octanol 325.1; isopropyl alcohol 313.2|Readily soluble in acetonitrile, DMSO, acetone|In water, 0.73 mg/L at pH 7, 20 °C)|In water, 0.50 to 0.67 mg/L at 20 °C

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water. /Residential users/

1.47X10-5 Torr /SRC: 1.47X10-5 mm Hg / at 25 °C

Henry's Law constant = 9.5X10-6 atm-cu m/mol at 25 °C (est)

Physicochemical data refer to a mixture with composition 93.0-98.8% metofluthrin; >95% (1R)-isomers, >98% trans-isomers, >86% (Z)-isomers /Technical/

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.|Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal. /Residential users/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it. /Residential users/

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label./Residential users/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide. To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash. /Residential users/

Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores. /Residential users/|Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself and your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them. /Residential users/|Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters. /Residential users/|Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face. /Residential users/

LC50 Rat inhalation > 1.08 and < 1.96 mg/L/4 hr|LD50 Rat dermal > or = 2,000 mg/kg|LD50 Rat oral > 2,000 mg/kg

Metofluthrin'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 33,000(SRC), determined from a structure estimation method(2), indicates that metofluthrin is expected to be immobile in soil(SRC). Volatilization of metofluthrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 1.47X10-5 mm Hg(3), and water solubility, 0.73 mg/L(3). However, adsorption to soil is expected to attenuate volatilization. Metofluthrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Metofluthrin is biodegraded aerobically with half-life rates of 1 to 8 days in sandy loam(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 33,000(SRC), determined from a structure estimation method(2), indicates that metofluthrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 9.5X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 1.47X10-5 mm Hg(4), and water solubility, 0.73 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7.5 and 60 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 31 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 51(SRC), from its log Kow of 5.0(4) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism(SRC). Metofluthrin is expected to undergo hydrolysis in the environment due to the presence of functional groups that hydrolyze under environmental conditions(3). Metofluthrin may biodegrade in water based on aerobic degradation rates of 1 to 8 days in sandy loam(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metofluthrin, which has a vapor pressure of 1.47X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase metofluthrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-lives for these reactions in air are estimated to be 5.8 and 5.2 hours(SRC), calculated from rate constants of 6.6X10-11 and 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC), for the cis and trans-isomers, respectively, that were derived using a structure estimation method(3). Vapor-phase metofluthrin is also degraded in the atmosphere by reaction with ozone(SRC); the half-lives for these reactions in air are estimated to be 2.1 and 1.4 hours(SRC), calculated from rate constants of 1.3X10-16 and 2.0X10-16 cu cm/molecule-sec at 25 °C(SRC), for the cis and trans-isomers, respectively, that were derived using a structure estimation method(3). Particulate-phase metofluthrin may be removed from the air by wet or dry deposition(SRC). Metofluthrin contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constants for the vapor-phase reaction of cis- and trans-metofluthrin with photochemically-produced hydroxyl radicals have been estimated as 6.6X10-11 and 7.4X10-11 cu cm/molecule-sec at 25 °C(SRC), respectively, using a structure estimation method(1). This corresponds to atmospheric half-lives of about 5.8 and 5.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constants for the vapor-phase reaction of cis- and trans-metofluthrin with ozone have been estimated as 1.3X10-16 and 2.0X10-16 cu cm/molecule-sec at 25 °C(SRC), respectively, that were derived using a structure estimation method(1). These correspond to atmospheric half-lives of about 2.1 and 1.4 hours, respectively, at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 4X10-2 L/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 5.5 years and 200 days at pH values of 7 and 8, respectively(3). Metofluthrin contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 51 was calculated in fish for metofluthrin(SRC), using a log Kow of 5.0(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of metofluthrin can be estimated to be 33,000(SRC). According to a classification scheme(2), this estimated Koc value suggests that metofluthrin is expected to be immobile in soil.

The Henry's Law constant for metofluthrin is estimated as 9.5X10-6 atm-cu m/mole(SRC) derived from its vapor pressure, 1.47X10-5 mm Hg(1), and water solubility, 0.73 mg/L(1). This Henry's Law constant indicates that metofluthrin is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 7.5 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 60 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 31 years if adsorption is considered(3). Metofluthrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

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

Male Sprague-Dawley rats were treated with 1 mg/kg/day of (Methoxymethylbenzyl-alpha -(14)C) S-1264RTZ (lot no. RIS2001-003, specific radioactivity: 6.19 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 2 times during study, (5/7/02) 99.2%, (5/17/02) 99.1%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin/ lot no. 010621G, purity: 99.3%). In the Excretion Study, three animals were dosed orally by gavage daily for 21 days with the test material and urine and fecal samples were collected up daily through 21 days and at 24, 48, and 72 hours and 5, 7, 10 and 14 days post-final dose. In the Tissue Distribution Study, 12 animals were dosed orally by gavage with the test material and 3 animals/time point were euthanized after 10, 16, and 21 doses and 7 days post-final dose. In the Excretion Study, 75% of the total administered dose was excreted in the urine and 22% in the feces. The liver and kidneys were the primary sites of radiolabel recovery over the course of the dosing period with the level of radioactivity stabilizing over the dosing period. At 14 days post-final dose, the liver, red blood cell and hair were the primary locations where the radiolabel was recovered. The level of radioactivity recovered from the stomach, small intestine, cecum and large intestine was stabilized or slightly increased over the course of the dosing period. Radiolabel recovered in the hair peaked at the time of the 16th dose. The radiolabel was not sequestered in the fat nor did a significant fraction of the administered dose pass across the blood:brain barrier. ... /Z-isomer/|Male Sprague-Dawley rats were treated with 1 mg/kg/day of (Carbonyl-(14)C) S-1264RTZ (lot no. RIS2000-019, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 2 times during study;(5/8/02) 98.6%, (5/16/02) 99.7%),. Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin/ lot no. 010621G, purity: 99.3%). In the Excretion Study, three animals were dosed orally by gavage daily for 21 days with the test material and urine and fecal samples were collected up daily through 21 days and at 24, 48, and 72 hours and 5, 7, 10 and 14 days post-final dose. In the Tissue Distribution Study, 12 animals were dosed orally by gavage with the test material and 3 animals/time point were euthanized after 10, 16, and 21 doses and 7 days post-final dose. In the Excretion Study, 57% of the total administered dose was excreted in the urine and 38% in the feces. The liver and kidneys were the primary sites of radiolabel recovery over the course of the dosing period with the level of radioactivity stabilizing over the dosing period. However, at 14 days post-final dose, the red blood cell and hair were the primary locations where the radiolabel was recovered. The level of radioactivity recovered from the stomach, small intestine, cecum and large intestine was stabilized over the course of the dosing period. Radiolabel recovered in the hair peaked at the time of the 21st dose. The radiolabel was not sequestered in the fat nor did a significant fraction of the administered dose pass across the blood:brain barrier. ... /Z-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Methoxymethylbenzyl-alpha -(14)C) S-1264RTZ (/metofluthrin z-isomer/ lot no. RIS2001-003, specific radioactivity: 6.19 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 4 times during study, (10/22/01) 99.1%, (10/31/01) 98.6%, (11/19/01) 99.1%, (11/26/01) 99.5%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin z-isomer/ lot no. 010621G, purity: 99.3%). In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 60 to 71% of the administered dose was excreted in the urine and 25 to 36% in the feces with little difference demonstrated between the two dosing levels. No radiolabel was recovered in the air sampling. Sixty eight to 84% of the administered dose was recovered in the 1st 24 hours post-dose. The time to maximal blood concentrations ranged from 4.0 to 8.0 hours post-dose. The liver and kidneys were the primary sites of radiolabel recovery over the course of the 7 day collection period. Radioassay of the stomach, small intestine, cecum and large intestine demonstrated a time-course of passage for the radiolabeled compound through the gastrointestinal tract. Radiolabel recovery in the hair peaked later than that observed in the systemic circulation. The radiolabel was not sequestered in the fat nor did a significant fraction of the administered dose pass across the blood:brain barrier. ... /Z-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Carbonyl-(14)C) S-1264RTE (/metofluthrin e-isomer/ lot no. RIS2000-020, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.2%; repurified 4 times during study, (3/18/02) 99.0%, (3/26/02) 98.1%, (4/15/02) 99.4%, (4/22/02) 99.2%;). Dosing preparations were supplemented with unlabeled S-1264RTE (/metofluthrin e-isomer/ lot no. 010831G, purity: 96.9%) . In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Biliary Excretion Study, four male rats, whose bile ducts had been cannulated, were dosed with 1 mg/kg of the test material. Bile, urine and fecal samples were collected through 72 hours post-dose. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 29 to 45% of the administered dose was excreted in the urine and 50 to 66% in the feces with little difference demonstrated between the two dosing levels. Air sampling recovered 0.4 to 0.6% of the administered dose. Sixty five to 78% of the administered dose was recovered in the 1st 24 hours post-dose. In the Bile Excretion Study, 27 and 55% of the dose was recovered in the bile of the males and females, respectively. The greater recovery of the radiolabel in the bile of the females resulted in a decrease of radioactivity recovered from the urine and the feces (urine: 45.1 to 20.4%, feces: 50.2 to 19.6%), For the males, only the urinary recovery of the radiolabel was decreased (37.1 to 9.6%). The males absorbed only 40% of the administered dose in contrast to the 77% demonstrated by the females. The time to maximal blood concentrations ranged from 4.7 to 6.7 hours post-dose, irrespective of the dosing level. The liver was the primary site of radiolabel recovery over the course of the 7 day collection period. Radioassay of the stomach, small intestine, cecum and large intestine demonstrated a time-course of passage for the radiolabeled compound through the gastrointestinal tract. Radiolabel recovery in the hair peaked later than that observed in the systemic circulation. The radiolabel was not sequestered in the fat nor did a significant fraction of the administered dose pass across the blood:brain barrier. ... /E-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Carbonyl-(14)C) S-1264RTZ (/metofluthrin z-isomer/ lot no. RIS2000-019, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 4 times during study, (12/3/01) 99.6%, (12/19/1) 98.2%, (2/18/02) 98.6%, (2/25/02) 98.9%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin z-isomer/ lot no. 010621G, purity: 99.3%). In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Biliary Excretion Study, four male rats, whose bile ducts had been cannulated, were dosed with 1 mg/kg of the test material. Bile, urine and fecal samples were collected through 72 hours post-dose. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 44 to 57% of the administered dose was excreted in the urine and 38 to 52% in the feces with little difference demonstrated between the two dosing levels. Air sampling recovered from 0.7 to 1.4% of the administered dose. Seventy four to 83% of the administered dose was recovered in the 1st 24 hours post-dose. In the Bile Excretion Study, 30 to 40% of the dose was recovered in the bile, 25 to 26% in the urine and 30 to 39% in the feces. The males and females demonstrated 58 and 68% absorption of the administered dose. The time to maximal blood concentrations ranged from 3.3 to 6.7 hours post-dose. The liver and kidneys were the primary sites of radiolabel recovery over the course of the 7 day collection period. Radioassay of the stomach, small intestine, cecum and large intestine demonstrated a time-course of passage for the radiolabeled compound through the gastrointestinal tract. Radiolabel recovery in the hair peaked later than that observed in the systemic circulation. The radiolabel was not sequestered in the fat nor did a significant fraction of the administered dose pass across the blood:brain barrier. ... /Z-isomer/

Male Sprague-Dawley rats were treated with 1 mg/kg/day of (Methoxymethylbenzyl-alpha -(14)C) S-1264RTZ (lot no. RIS2001-003, specific radioactivity: 6.19 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 2 times during study, (5/7/02) 99.2%, (5/17/02) 99.1%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin/ lot no. 010621G, purity: 99.3%). In the Excretion Study, three animals were dosed orally by gavage daily for 21 days with the test material and urine and fecal samples were collected up daily through 21 days and at 24, 48, and 72 hours and 5, 7, 10 and 14 days post-final dose. In the Tissue Distribution Study, 12 animals were dosed orally by gavage with the test material and 3 animals/time point were euthanized after 10, 16, and 21 doses and 7 days post-final dose. In the Excretion Study, 75% of the total administered dose was excreted in the urine and 22% in the feces. ... Based upon the isolated metabolites, the major pathways of metabolism were cleavage of the ester linkage, oxidation of methyl groups on the benzyl moiety of the molecule to form alcohol, aldehyde and carboxylic acid metabolites, reduction of the double bond in the acid moiety of the molecule, and the formation of glutathione and sulfate adducts. /Z-isomer/|Male Sprague-Dawley rats were treated with 1 mg/kg/day of (Carbonyl-(14)C) S-1264RTZ (/metofluthrin/ lot no. RIS2000-019, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 2 times during study;(5/8/02) 98.6%, (5/16/02) 99.7%),. Dosing preparations were supplemented with unlabeled S-1264RTZ (lot no. 010621G, purity: 99.3%). In the Excretion Study, three animals were dosed orally by gavage daily for 21 days with the test material and urine and fecal samples were collected up daily through 21 days and at 24, 48, and 72 hours and 5, 7, 10 and 14 days post-final dose. In the Tissue Distribution Study, 12 animals were dosed orally by gavage with the test material and 3 animals/time point were euthanized after 10, 16, and 21 doses and 7 days post-final dose. In the Excretion Study, 57% of the total administered dose was excreted in the urine and 38% in the feces. ... Based upon the isolated metabolites, the major pathways of metabolism were cleavage of the ester linkage, oxidation of methyl groups in the acid moiety of the molecule to form alcohol, aldehyde and carboxylic acid metabolites, reduction of the double bond in the acid moiety of the molecule, and the formation of glutathione, sulfate and glucuronide adducts. /Z-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Methoxymethylbenzyl-alpha -(14)C) S-1264RTZ (/metofluthrin z-isomer/ lot no. RIS2001-003, specific radioactivity: 6.19 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 4 times during study, (10/22/01) 99.1%, (10/31/01) 98.6%, (11/19/01) 99.1%, (11/26/01) 99.5%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin z-isomer/ lot no. 010621G, purity: 99.3%). In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 60 to 71% of the administered dose was excreted in the urine and 25 to 36% in the feces with little difference demonstrated between the two dosing levels. ... Based upon the isolated metabolites, the major pathways of metabolism were cleavage of the ester linkage, oxidation of methyl groups in the acid moiety of the molecule to form alcohol, aldehyde and carboxylic acid metabolites, reduction of the double bond in the acid moiety of the molecule, and the formation of glutathione, sulfate and glucuronide adducts. /Z-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Carbonyl-(14)C) S-1264RTE (/metofluthrin e-isomer/ lot no. RIS2000-020, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.2%; repurified 4 times during study, (3/18/02) 99.0%, (3/26/02) 98.1%, (4/15/02) 99.4%, (4/22/02) 99.2%;). Dosing preparations were supplemented with unlabeled S-1264RTE (/metofluthrin e-isomer/ lot no. 010831G, purity: 96.9%) . In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Biliary Excretion Study, four male rats, whose bile ducts had been cannulated, were dosed with 1 mg/kg of the test material. Bile, urine and fecal samples were collected through 72 hours post-dose. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 29 to 45% of the administered dose was excreted in the urine and 50 to 66% in the feces with little difference demonstrated between the two dosing levels. ... Based upon the isolated metabolites, the major pathways of metabolism were cleavage of the ester linkage, oxidation of methyl groups in the acid moiety of the molecule to form alcohol, aldehyde and carboxylic acid metabolites, reduction of the double bond in the acid moiety of the molecule, and the formation of a sulfate adduct. /E-isomer/|Sprague-Dawley rats of both sexes were treated with 1 or 20 mg/kg of (Carbonyl-(14)C) S-1264RTZ (/metofluthrin z-isomer/ lot no. RIS2000-019, specific radioactivity: 6.50 Mbq/mg; radiochemical purity: (12/00) 99.4%; repurified 4 times during study, (12/3/01) 99.6%, (12/19/1) 98.2%, (2/18/02) 98.6%, (2/25/02) 98.9%). Dosing preparations were supplemented with unlabeled S-1264RTZ (/metofluthrin z-isomer/ lot no. 010621G, purity: 99.3%). In the Excretion Study, four animals/sex/group were dosed orally by gavage with 1 or 20 mg/kg of the test material and urine and fecal samples were collected up to 7 days post-dose. Air samples were collected through 72 hours. In the Biliary Excretion Study, four male rats, whose bile ducts had been cannulated, were dosed with 1 mg/kg of the test material. Bile, urine and fecal samples were collected through 72 hours post-dose. In the Pharmacokinetics Study, 3 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and blood samples were drawn at specified time intervals up to 7 days post-dose. In the Tissue Distribution Study, 12 animals/sex/group were dosed with 1 or 20 mg/kg of the test material and 3 animals/sex/group/time point were euthanized at specified time intervals post-dose and the concentration of radiolabel in particular tissues was determined. In the Excretion Study, 44 to 57% of the administered dose was excreted in the urine and 38 to 52% in the feces with little difference demonstrated between the two dosing levels. Air sampling recovered from 0.7 to 1.4% of the administered dose. Seventy four to 83% of the administered dose was recovered in the 1st 24 hours post-dose. In the Bile Excretion Study, 30 to 40% of the dose was recovered in the bile, 25 to 26% in the urine and 30 to 39% in the feces. ... Based upon the isolated metabolites, the major pathways of metabolism were cleavage of the ester linkage, oxidation of methyl groups in the acid moiety of the molecule to form alcohol, aldehyde and carboxylic acid metabolites, reduction of the double bond in the acid moiety of the molecule, and the formation of glutathione, sulfate and glucuronide adducts. /Z-isomer/

/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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Pyrethrins, pyrethroids, and related compounds/|/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 necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. 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. Administer activated charcoal ... . /Pyrethrins, pyrethroids, and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for air way control in the patient who is unconscious or is in severe respiratory distress. Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) 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 ... . /Pyrethrins, pyrethroids, and related compounds/|Skin decontamination. Wash skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/|For more Antidote and Emergency Treatment (Complete) data for Metofluthrin (9 total), please visit the HSDB record page.

/GENOTOXICITY/ Primary hepatocyte cultures of ... fresh female human hepatocytes were exposed to 50 uM of S-1264 (/metofluthrin/ purity not reported) or 50 uM of phenobarbital for 3 days. The activity of 7-pentoxyresorufin O-depentylase and the CYP2B mRNA content in the hepatocytes were assayed at the conclusion of the incubation period. Treatment with S-1264 resulted in an increase in 7-pentoxyresorufin O-depentylase activity and a 2 to 3 fold increase in the CYP2B mRNA content above that of the control levels for the ... human hepatocyte cultures. ... Phenobarbital increased the enzyme activity and the mRNA levels in all of the hepatocyte cultures.

(2,3,5,6-tetrafluoro-4-methoxymethylphenyl)methyl-2,2-dimethyl-3-(1-propenyl)cyclopropanecarboxylate

Liquid vaporizers (discontinued term); mosquito coil|Composition: Technical is 93.0-98.8% metofluthrin; >95% (1R)-isomers, >98% trans-isomers, >86% (Z)-isomers.|Coils|Norm 1 (S.C. Johnson & Son Inc.) 31.2% Metofluthrin|For more Formulations/Preparations (Complete) data for Metofluthrin (7 total), please visit the HSDB record page.

Product analysis by gas chromatography.