2,2-디메틸-3-(1-프로펜-1-일)사이클로프로판카복실산 [2,3,5,6-테트라플루오로-4-(메톡시메틸)페닐]메틸

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).

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.

/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.

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).

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).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Twelve Wistar rats/sex/group received 0, 100, 300, 1000 or 2500 ppm of S-1264 (/metofluthrin/ lot no. PK-010501 G, purity: 94.9%) in the diet for 13 weeks ((M) 0, 6.85, 20.6, 70.4 and 183.6 mg/kg/day, (F) 0, 7.51, 21.6, 73.0, 185.6 mg/kg/day). One female in the 2500 ppm group died on day 4. The mean body weights of both sexes in the 2500 ppm group were less than those of the control group ((M) p<0.01, (F) NS). The Functional Observational Battery did not reveal any treatment-related signs. There was no treatment-related effect upon food consumption. The ophthalmology examination did not reveal any treatment-related effect. Although the number and relative concentration of basophils in the blood of the 2500 ppm females was less than that of the controls, no treatment-related effect was apparent in the overall hematology profile for these animals. The mean serum cholesterol and phospholipid levels were elevated for the males in the 1000 ppm group and for both sexes in the 2500 ppm group (p<0.01). The total protein and albumin levels in the serum were increased for the 2500 ppm males (p<0.01). The 1000 ppm males also demonstrated an increase in total protein (p<0.01). The males in the 1000 and 2500 ppm groups exhibited increased levels of leucocytes in the urine (p<0.01). The mean absolute and relative liver weights of the 1000 ppm males and both sexes in the 2500 ppm group were greater than those values for the control group (p<0.01). The mean relative kidney weights were greater for both sexes in the 2500 ppm group (p<0.01 or 0.05). The mean relative spleen weight of the 2500 ppm males was greater than that of the control (p<0.05). In the histopathology examination, hepatocellular hypertrophy and basophilia in the liver were evident for both the sexes in the 2500 ppm group and for the males in the 300 and 1000 ppm groups (hepatocellular hypertrophy: (M) 0: 1/12 vs. 300: 5/12, 1000: 10/12, 2500: 12/12, (F) 0: 0/12 vs. 2500: 5/12; hepatocellular basophilia: (M) 0: 0/12 vs. 300: 5/12, 1000: 12/12, 2500: 12/12; (F) 0: 0/12 vs. 2500: 4/12). An increasing severity of hyaline droplet formation was noted in the kidneys of the 2500 ppm males (grade 3: 0: 1/12 vs. 2500: 7/12). Target organs: liver and kidneys ... . Subchronic dietary NOEL: (M 100 ppm (6.9 mg/kg/day) (based upon the incidence of hepatocellular hypertrophy and basophilia in the livers of the 300 ppm males), (F) 300 ppm (21.6 mg/kg/day) (based upon increased relative liver weights for the females in the 1000 ppm group).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ Ten Crj:CD (SD) rats/sex/group were exposed nose-only to 0 (corn oil vehicle), 9.84, 50.6, 98.7 and 196 mg/cu m (analytical) of S-1264 /metofluthrin/; lot no. PK-010501 G, purity: 94.9%) 4 hours/day for 4 weeks. The mean mass medium aerodynamic diameter (MMAD) ((geometric standard deviation) (GSD)) values were 2.67 (2.17), 3.02 (2.00), 2.47 (2.02) and 2.94 (2.25) um, respectively. Seven males and three females in the 196 mg/m3 died during the study. Clinical signs of tremors, hypersensitivity and clonic convulsions were noted for the animals in this group, particularly during the first week of the exposure. Six of the 10 animals which died succumbed during the first week. There was no treatment-related effect upon the mean body weights. The mean food and water consumption for the both sexes in the 196 mg/cu m exposure group were less than those values for the control group (p<0.01, 0.05 or NS) during the first week of exposure. There was no effect on these parameters during the remainder of the exposure period. The ophthalmology, hematology, clinical chemistry and urinalysis did not reveal any treatment-related effects. The necropsy and histopathological examinations did not reveal any treatment-related lesions or effect on organ weights. Possible adverse effect: tremors and clonic convulsions; 4-Week Inhalation Exposure NOEL: (M/F) 98.7 mg/cu m (based upon the clinical signs demonstrated by both sexes in the 196 mg/cu m exposure group).

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).

Metofluthrin's production may result in its release to the environment through various waste streams; its use as an insecticide will result in its direct release to the environment. If released to air, a vapor pressure of 1.47X10-5 mm Hg at 25 °C indicates metofluthrin will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase metofluthrin will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 5.8 and 5.2 hours for the cis- and trans-isomers, respectively. Vapor-phase metofluthrin will also be degraded in the atmosphere by reaction with ozone; the half-life for this reaction in air is estimated to be 2.1 and 1.4 hours for the cis- and trans-isomers, respectively. Particulate-phase metofluthrin will be removed from the atmosphere by wet or dry deposition. Metofluthrin contains chromophores that absorb at wavelengths >290 nm and therefore may be susceptible to direct photolysis by sunlight. If released to soil, metofluthrin is expected to have no mobility based upon an estimated Koc of 33,000. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 9.5X10-6 atm-cu m/mole. However, adsorption to soil is expected to attenuate volatilization. Metofluthrin is biodegraded aerobically with half-lives of 1 to 8 days in sandy loam. If released into water, metofluthrin is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 7.5 and 60 days, respectively. 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. An estimated BCF of 51 suggests the potential for bioconcentration in aquatic organisms is moderate, provided the compound is not metabolized by the organism. Hydrolysis is expected to be an important environmental fate process since this compound contains functional groups that hydrolyze under environmental conditions. 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)

/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.

For metofluthrin (USEPA/OPP Pesticide Code: 109709) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticides (pyrethroid ester insecticides)

For mosquito control.

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.