Flucythrinate
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Flucythrinate
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CAS No:
70124-77-5
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Formula:
C26H23F2NO4
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Chemical Name:
Flucythrinate
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Synonyms:
Benzeneacetic acid,4-(difluoromethoxy)-α-(1-methylethyl)-,cyano(3-phenoxyphenyl)methyl ester;AC 222705;CyBolt;Pay-Off;Flucythrinate;Fluorocythrin;α-Cyano-3-phenoxybenzyl 2-[p-(difluoromethoxy)phenyl]isovalerate;Flucythrinate I;Flucythrinate II;71611-31-9;102984-46-3;2048189-80-4;2048190-24-3
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CAS No:
Flucythrinate Basic Attributes
451.46
451.46
274-322-7
57D0GAO3RX
DTXSID0022301
Viscous liquid
2926909037
Characteristics
68.6
6.20
1.189 g/cm3 @ Temp: 22 °C
<25 °C
108 °C @ Press: 0.35 Torr
-18 °C
1.553
In water, 0.06 mg/L at 25 deg C
APPROX 4°C
1.2×10 -6 Pa (25 °C)
Oral-Rat LD50: 67 mg/kg; Oral-Mouse LD50: 76 mg/kg
Flammable; burning produces toxic nitrogen oxides and fluoride gases
Henry's Law constant = 8.61X10-8 atm-cu m/mol at 25 °C (est)
Dark amber viscous liquid, with a faint ester-like odor. /Technical flucythrinate/|Hydroxyl radical reaction rate constant = 6.26X10-11 cu cm/molec-sec at 25 °C (est)
Safety Information
UN28106.1/PG3
3
20/21-25-50/53-67-65-38-11
36/37-45-60-61-62
CY1578620
T,N,Xn,F
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Hydrolysis rates (half-lives in days): ca 40 at pH3, 52 at pH6, 6.3 at pH 9, 40 in distilled water (all at 27 deg C; ca 40 at pH 3, 31 at pH 6, 2.6 at pH 9, 29 in distilled water (all at 35 deg C).
P261-P273-P280-P301 + P310-P311-P501
H301 + H331-H312-H410
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.|Pesticide Disposal: Pesticides that cannot be used according to formulating instructions must be disposed according to Federal, State or local procedures under Subtitle C of RCRA. Container Disposal: Triple rinse or equivanent and offer for recycling or reconditioning or puncture and dispose of at a sanitary landfill following approved Dtate and local procedures.|Incineration would be an effective disposal procedure where permitted. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. /Pyrethrin products/
Incompatibility: Strong oxidizers. /Pyrethrins/
Clark JR et al; Toxicity of pyrethroids to Marine Invertebrates and Fish: A Literature Review and Test Results with Sediment-Sorbed Chemicals. Environ Toxicol Chem 8 (5): 393-401 (1989). Data on acute and chronic toxicity of permethrin, fenvalerate, cypermethrin, and flucythrinate to marine invertebrates and fishes are reviewed.
|Danger|H226 (67.44%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P303+P361+P353, P304+P340, P310, P311, P312, P314, P320, P321, P322, P330, P363, P370+P378, P391, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 129 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/|Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/|Wear protective clothing and rubber gloves.|Wear appropriate equipment to prevent: Repeated or prolonged skin contact. /Pyrethrum and pyrethrins/|For more Personal Protective Equipment (PPE) (Complete) data for FLUCYTHRINATE (14 total), please visit the HSDB record page.
/Pyrethrins/ ... burn with difficulty. /Pyrethrins/
Extinguish fire using agent suitable for type of surrounding fire. /Pyrethrins/|If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.). Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, solid, toxic/|If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, toxic, flammable/|If material on fire or involved in fire: Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. Cool all affected containers with flooding quantities of water. Keep run-off water out of sewers and water sources. /Pyrethroid pesticide, liquid, toxic/
Extremely toxic to fish and aquatic organisms. Do not apply directly tl lakes, ponds, or streams. Do not contaminate water by the cleaning of equipment or disposal of wastes.|Environmental consideration - Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, or cement powder. /Pyrethrins/|Environmental consideration - Water spill: If /pyrethrins/ are dissolved, apply activated carbon at ten times the spilled amount in the region of 10 ppm or greater concn. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Pyrethrins/
Wash thoroughly with soap and water after handling and before eating or smoking. Remove contaminated clothing and wash before reuse. Harmful if inhaled. Avoid breathing vapor or spray mist.|Use with adequate ventilation, and wear goggles or a face shield when handling.|Avoid eye, skin, clothing contact. May be fatal if swallowed or absorbed through skin; ... Use with adequate ventilation... Wash thoroughly after handling.|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.|For more Preventive Measures (Complete) data for FLUCYTHRINATE (16 total), please visit the HSDB record page.
/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Pyrethroid pesticide, liquid, flammable, poisonous; Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Pyrethroid pesticide, liquid, flammable, poisonous; Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Pyrethroid pesticide, liquid, flammable, poisonous; Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Pyrethroid pesticide, liquid, flammable, poisonous; Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for FLUCYTHRINATE (16 total), please visit the HSDB record page.
Immediately irritating to the eye. /Pyrethrins/|Some pyrethroid (eg, deltamethrin, fenvalerate, cyhalothrin, lambda-cyhalothrin, flucythrinate, and cypermethrin) may cause a transient itching and/or burning sensation in exposed human skin. /Pyrethroids/
Toxicity
highly toxic
Piperonyl butoxide potentiates /insecticidal activity/ of pyrethrins by inhibiting the hydrolytic enzymes responsible for pyrethrins' metabolism in arthropods. When piperonyl butoxide is combined with pyrethrins, the insecticidal activity of the latter drug is increased 2-12 times /Pyrethrins/|At dietary level of 1000 ppm pyrethrins & 10000 ppm piperonyl butoxide ... /enlargement, margination, & cytoplasmic inclusions in liver cells of rats/ were well developed in only 8 days, but ... were not maximal. Changes were proportional to dosage & similar to those produced by DDT. Effects of the 2 materials were additive. /Pyrethrins/|Male Sprague-Dawley rats dosed with N-nitrosodiethylamine (NDEA) 24 hr after two-thirds partial hepatectomy were treated with t... flucythrinate ... in the diet for 20 weeks. Altered hepatic foci were analyzed by quantitative stereology from paraffin-embedded sections stained for gamma-glutamyltranspeptidase (GGT) or glutathione S-transferase P (GST-P)... /and flucythrinate enhanced/ ...the development of NDEA-initiated, GGT-positive foci in rat liver at non-hepatotoxic doses. On the contrary, the volume fractions of GST-P-positive foci were not elevated as compared to the control group. /Flucythrinate/ ... inhibited the transfer of Lucifer Yellow CH between WB-F344 rat liver epithelial cells in culture, supporting the increase of GGT-positive foci and suggesting that these substances can act as tumour promoters. The discrepancy between the results from analyses using GGT or GST-P as markers emphasizes the importance of understanding the mechanism underlying the expression of different markers for preneoplastic lesions and the importance of such effects in tumor promotion.
LD50 Rat male oral 81 mg/kg|LD50 Rat oral 67 mg/kg|LD50 Rabbit percutaneous >1000 mg/kg|LC50 Rat inhalation 4850 mg/cu m/4 hr|LD50 Mice oral 76 mg/kg
/AQUATIC SPECIES/ Data on the acute and chronic toxicities of permethrin, fenvalerate, cypermethrin and flucythrinate to marine invertebrates and fish are reviewed. Generally, crustaceans are more sensitive than fish; oysters are comparatively insensitive. The mysid Mysidopsis bahia consistently is among the most sensitive crustaceans tested, with 96-hr LC50s of <0.02 ug/L for permethrin and of <0.01 ug/L for fenvalerate, cypermethrin and flucythrinate. The potential for chronic toxicity to fish is minimal for permethrin, moderate for fenvalerate and relatively great for flucythrinate.
Flucythrinate's former production in the US may have resulted in its release to the environment through various waste streams; its use as an insecticide(1) resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 56,000(SRC), determined from a log Kow of 6.2(2) and a regression-derived equation(3), indicates that flucythrinate is expected to be immobile in soil(SRC). Volatilization of flucythrinate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.6X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 8.7X10-9 mm Hg(4), and water solubility, 0.06 mg/L(4). Flucythrinate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Laboratory tests have shown that flucythrinate photodegrades on glass and plant surfaces(5). A degradation of 28.6 and 45.6% in 6 weeks using a commerce silt loam soil under dry conditions and amended with organic matter, respectively(6), indicates that biodegradation may not be an important environmental fate process in soil(SRC). A field study measured flucythrinate half-lives of 9.4-11.9 days in an agricultural soil(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 56,000(SRC), determined from a log Kow of 6.20(2) and a regression-derived equation(3), indicates that flucythrinate 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 8.6X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 8.7X10-9 mm Hg(4), and water solubility, 0.06 mg/L(4). According to a classification scheme(5), an estimated BCF of 12,000(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is very high, provided the compound is not metabolized by the organism(SRC). Flucythrinate is rapidly hydrolyzed in water under alkaline conditions, but more slowly under neutral or acidic conditions(7). Reported hydrolysis half-lives at 27 °C are about 40 days at pH 3, 52 days at pH 5, and 6.3 days at pH 9(8). A half-life of about 16 days in sediment and seawater collected from a salt marsh(8) suggests that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), flucythrinate, which has a vapor pressure of 8.7X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase flucythrinate may be removed from the air by wet or dry deposition(SRC). Flucythrinate absorbs light strongly at wavelengths >290 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
Flucythrinate is rapidly hydrolyzed in water under alkaline conditions, but more slowly under neutral or acidic conditions(1). Reported hydrolysis half-lives at 27 °C are about 40 days at pH 3, 52 days at pH 5, and 6.3 days at pH 9(1). Flucythrinate was degraded on soil plates by simulated sunlight and in aqueous solutions with half-lives of about 21 and 4 days, respectively(1), and therefore it may be susceptible to direct photolysis by sunlight(SRC). Flucythrinate absorbs light strongly in the environmental spectra (>290 nm)(2); when exposed to sunlight, thin films of flucythrinate on glass surfaces were observed to have a half-life of about 8 days(2); on bean leaves, the photodegradation half-life was about 3 days(2); only minor degradation occurred on dark control glass and leaf surfaces(2); the faster rate on leaf surfaces was thought to result from photo-sensitization by chlorophyll and plant waxes(2). In a seawater solution study, flucythrinate had a 6.1 day half-life when exposed to sunlight, but only a 38 day half-life under no-sunlight conditions(3).
An estimated BCF of 12,000 was calculated in fish for flucythrinate(SRC), using a log Kow of 6.2(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, provided the compound is not metabolized by the organism(SRC). In a 28-day laboratory study, a steady-state BCF of 2300 was measured in eastern oysters (Crassostrea virginica)(4).
1.00e+05 L/kg|The Koc of flucythrinate is estimated as 56,000(SRC), using a log Kow of 6.20(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that flucythrinate is expected to be immobile in soil. In a field study conducted in New Delhi, India (farm soil, pH 8.1 organic content 0.3%) flucythrinate did not leach below a 7.5 cm depth after a 40-day observation period(4).
The Henry's Law constant for flucythrinate is estimated as 8.6X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 8.7X10-8 mm Hg(1), and water solubility, 0.06 mg/L(1). This Henry's Law constant indicates that flucythrinate is expected to be essentially nonvolatile from water surfaces(2). Flucythrinate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Flucythrinate was not detected as part of the Danish National Pesticide Monitoring Program for January 1995 through December 1996 sampling of 4,182 food samples(1). It was not detected in brown rice, potato, cabbage, lettuce, carrot, cucumber, shiitake, apple, strawberry, and banana samples in Japan, detection limit 0.01 ppm(2). Flucythrinate was not detected on 710 domestic and 949 imported pears nor 1219 domestic and 114 imported tomatoes sampled in 1992-1993, as part of the US Food and Drug Administration Pesticide Program(3).
Occupational exposure and general population exposure should be low or non-existent since flucythrinate is no longer produced or used in the US (Sept, 1995). In the past, flucythrinate was applied directly to crops as a spray and exposure to this compound was primarily by inhalation and dermal routes in the field where it was applied. (SRC)
Drug Information
Flucythrinate is rapidly metabolized by ester cleavage and oxidation. When radio-labeled flucythrinate was administered orally to rats, 15 to 24% was eliminated in the urine and 37 to 65.6% was eliminated in the feces during the first 24 hours. Within 8 days, 95.8 to 100% of the dose was eliminated in either urine or feces. A large amount of the chemical recovered in the feces was unaltered flucythrinate, suggesting that this portion passed through the gut without being absorbed into the bloodstream. Metabolites of flucythrinate are considered to be of no toxicological significance.|In rats, following oral administration, 60-70% is eliminated within 24 hours, and >95% within 8 days, in the feces and urine. In the feces, the parent compound makes up most of the material excreted, but in the urine and in tissue, several metabolites are present. The major route of degradation is through hydrolysis, with subsequent hydroxylation of the hydrolysis products.|Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/|Although limited absorption may account for the low toxicity of some pyrethroids, rapid biodegradation by mammalian liver enzymes (ester hydrolysis and oxidation) is probably the major factor responsible. Most pyrethroid metabolites are promptly excreted, at least in part, by the kidney. /Pyrethroids/
Flucythrinate is rapidly metabolized by ester cleavage and oxidation.|The metabolic pathways for the breakdown of the pyrethroids vary little between mammalian species but vary somewhat with structure. ... Essentially, pyrethrum and allethrin are broken down mainly by oxidation of the isobutenyl side chain of the acid moiety and of the unsaturated side chain of the alcohol moiety with ester hydrolysis playing and important part, whereas for the other pyrethroids ester hydrolysis predominates. /Pyrethrum and pyrethroids/|The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid and alcohol components, since direct injection into the mammalian CNS leads to a susceptibility similar to that seen in insects. Some additional resistance of homeothermic organisms can also be attributed to the negative temperature coefficient of action of the pyrethroids, which are thus less toxic at mammalian body temperatures, but the major effect is metabolic. Metabolic disposal of the pyrethroids is very rapid, which means that toxicity is high by the intravenous route, moderate by slower oral absorption, and often unmeasureably low by dermal absorption. /Pyrethroids/|Pyrethrins are reportedly inactivated in the GI tract following ingestion. In animals, pyrethrins are rapidly metabolized to water soluble, inactive compounds. /Pyrethrins/|Synthetic pyrethroids are generally metabolized in mammals through ester hydrolysis, oxidation, and conjugation, and there is no tendency to accumulate in tissues. In the environment, synthetic pyrethroids are fairly rapidly degraded in soil and in plants. Ester hydrolysis and oxidation at various sites on the molecule are the major degradation processes. /Synthetic pyrethroids/
The synthetic pyrethroids delay closure of the sodium channel, resulting in a sodium tail current that is characterized by a slow influx of sodium during the end of depolarization. Apparently the pyrethroid molecule holds the activation gate in the open position. Pyrethroids with an alpha-cyano group (e.g., fenvalerate) produce more prolonged sodium tail currents than do other pyrethroids (e.g., permethrin, bioresmethrin). The former group of pyrethroids causes more cutaneous sensations than the latter. /Synthetic pyrethroids/|Interaction with sodium channels is not the only mechanism of action proposed for the pyrethroids. Their effects on the central nervous system have led various workers to suggest actions via antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, or actions on calcium ions. Since neurotransmitter specific pharmacological agents offer only poor or partical protection against poisoning, it is unlikely that one of these effects represents the primary mechanism of action of the pyrethroids, and most neurotransmitter release is secondary to increased sodium entry. /Pyrethroids/|Electrophysiologically, pyrethrins cause repetitive discharges and conduction block. /Pyrethrins/|The interaction of a series of pyrethroid insecticides with the sodium channels in myelinated nerve fibers of the clawed frog, Xenopus laevis, was investigated using the voltage clamp technique. Of 11 pyrethroids, 9 insecticidally active cmpd induced a slowly decaying sodium tail current on termination of a step depolarization, whereas the sodium current during depolarization was hardly affected. /Pyrethroids/|For more Mechanism of Action (Complete) data for FLUCYTHRINATE (8 total), please visit the HSDB record page.
/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 FLUCYTHRINATE (6 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ Experimental application of flucythrinate to the ear lobe of human volunteers at 130 ug/cm sq caused a marked paraesthesia which began 30 min after application and persisted for 24 hr. Flucythrinate produced the most severe paresthesia of the four pyrethroids tested. A second study using forearm skin and application at 13.8 mg/cm sq produced paresthesia after a delay of 4-5 hr lasting for 3 days, indicating that the thinner facial skin is more sensitive than other areas.|/SIGNS AND SYMPTOMS/... The most prominent health symptom that accompanies topical contact with these agents appears to be a cutaneous sensation, paresthesia. In this investigation, a substantial difference in the degree of paresthesia was noted between the formulated grade of 4 synthetic pyrethroids. Also, dl-alpha tocopheryl acetate was statistically validated as an efficacious therapeutic agent for cutaneous exposure to these insecticides. /Synthetic pyrethroids/|/SIGNS AND SYMPTOMS/ May be fatal if ingested or absorbed through the skin.|/SIGNS AND SYMPTOMS/ The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/|For more Human Toxicity Excerpts (Complete) data for FLUCYTHRINATE (6 total), please visit the HSDB record page.
AC 222,705
Flucythrinate Use and Manufacturing
The preparation method 1 is synthesized by 2-p-methoxyphenyl isovaleric acid through resolution (ineffective body racemate), hydrolysis, trifluoromethylation, acid chloride, esterification. The total yield including racemization and recovery can reach more than 75%. Resolution of 2-p-methoxyphenyl isovaleric acid 27g 2-p-methoxyphenyl isovaleric acid, 15g (-) 2-phenylethylamine, 1500mL 60% ethanol, dissolved by heating, cooling crystallization, recrystallization 14.5g white needle-like crystals; combining mother liquor, evaporating ethanol, and standing, filtering, and recrystallizing to obtain 3.5g white crystals; combining two crystals to obtain a total of 8g solids. Add 200 mL of water and 10 mL of concentrated hydrochloric acid. Heating and cooling gave 11.5g white solid, mp 136~138℃, [α]20D=+52.2o, yield 42.6%, optical purity 99.24%. (S) Preparation of (+)-2-p-hydroxyphenylisovaleric acid Add 10g of the product from the previous step, add 40mL of 48% hydrobromic acid and 2mL of glacial acetic acid. Heating 126~130℃, refluxing for 3h, cooling and recrystallizing to obtain 9g white needle crystal, mp189~191℃, [α]20D=+52.4o, yield 96.5%. (S) Preparation of (+)-2-p-difluoromethoxyphenyl isovaleric acid Add 10g of the previous step product to 19g of sodium hydroxide, 30mL of water, 60mL of dioxane, heat to 80 ℃, through the fluoride Plenium-22 about 40g, cooled, poured into 250mL water, washed with ether, the aqueous solution was acidified with concentrated hydrochloric acid, extracted with ether, the extract was dried over anhydrous sodium sulfate, and the ether was distilled off to obtain a light brown lump, using 1:1 Extracted with n-hexane-dichloromethane, the remaining white powder is 5.1g, mp 189~191℃, [α]20D=+2.4o. The extract was evaporated to dryness under reduced pressure to obtain 5.5 g of light orange semi-solid, [α]20D=+40.2o, yield 3.7%, optical purity 99.5%. (S) Preparation of 2-p-difluoromethoxyphenyl isovaleryl chloride Add 1.7g ([α]20D=+40.2o) of the previous step, toluene 25mL, sulfoxide chloride 1mL, dimethylformamide 1 drop, heated to reflux for 0.5h, cooled, and distilled off toluene under reduced pressure to obtain 1.9g of orange viscous liquid, [α]20D=+37.4o. $4 Synthesis of Fenvalerate 1.31g m-phenoxybenzaldehyde, 0.2g tetrabutylammonium bromide, 25mL toluene, 1.5g potassium cyanide and 3mL water are added dropwise at room temperature (S) (+ )-2-p-difluoromethoxyphenyl isovaleryl chloride-toluene mixed solution 10mL (acid chloride 1.9g), stirred for 1h after dropping, added 10mL water, respectively with 10% Na2CO3, water, 10% HCl, saturated Each was washed once with 10 mL of brine, dried over anhydrous sodium sulfate, and toluene was distilled off under reduced pressure to obtain 3.7 g of dark red viscous liquid. Separated by silica gel column chromatography, collected about 10mL of light yellow band liquid, distilled off the solvent to obtain 3.1g of light green viscous liquid, 19D=1.5460, [α]20D=-5.43o, yield 99%, optical purity 98.5%. (R)-2-p-methoxyphenyl isovaleric acid racemization reaction, (R)-2-p-methoxyisovaleric acid produced by the reaction racemization (yield up to 98.5%), To improve the total yield of this synthetic route.
Insecticide.
(1989) 45,000 lbs active ingredient; (1982) 20,000 lb active ingredient; (1976) 0 lbs active ingredient; (1971) 0 lbs active ingredient; (1966) 0 lbs active ingredient
Emulsifiable concentrate, wettable powder.
The WHO Recommended Classification of Pesticides by Hazard identifies Flucythrinate (technical grade) as Class IB: highly hazardous; Main Use: insecticide.|Synthetic pyrethroid insecticide with contact and stomach poison activity.|/Pyrethroids/ are modern synthetic insecticides similar chemically to natural pyrethrins, but modified to increase stability in the natural environment. /Pyrethroids/|(1995) Food tolerances for residues removed /US/
Product analysis is by high performance liquid chromatography and gas liquid chromatography. Residues may be determined by gas liquid chromatography.|Pyrethrins ... in pesticide formulations are analyzed using gas chromatography equipped with flame ionization detection. Average recovery is 98% with a precision of 0.0044-0.011. /Pyrethrins/|... Liquid chromatography method has been developed to quantitate pyrethrins in pesticide formulations. ... Detection was monitored at 240 nm. ... Percent coefficients of variation ranged from 1.39 to 9.68 with the majority less than 5.00. ... /Pyrethrins/|Pyrethrins were detected in soils by gas chromatography after extraction with hexane. /Pyrethrins/|Low level pyrethrin formulations are extracted with tetrahydrofuran and determined via capillary gas chromatography with electron capture detection. ... Analysis of 5 formulations gave an average standard deviation of 3.3%. /Pyrethrins/
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:451.5
XLogP3:6.2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:10
Exact Mass:451.15951454
Monoisotopic Mass:451.15951454
Topological Polar Surface Area:68.6
Heavy Atom Count:33
Complexity:650
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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