68359-37-5CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)c1ccc(F)c(Oc2ccccc2)c1QQODLKZGRKWIFG-UHFFFAOYSA-NCyfluthrin appears as a viscous amber partly crystalline oil. Used as an insecticide.
Pesticides
Pesticide -> EPA IRIS
Acaricides, Insecticides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Pyrethrins/Pyrethroids
Environmental transformation -> Pesticides (parent, predecessor)
log Kow = 5.95
5.9
5.93
1.34 g/cu cm at 22 °C
Density (at 20 °C): 1.27 g/cm³
Yellowish-brown oil
Colorless crystals
>1000 g/L dichloromethane
In water, 3.0X10-3 mg/L at 20 °C
Solubility in water, mg/l at 20 °C: 0.003
60 °C
Crystals from m-hexane; mp: 68-69 °C; specific optical rotation: -2.1 deg at 20 °C/D (concentration by volume= 1.0 g in 100 ml chloroform) /(1R)(3S)(alpha S)-cyfluthrin/
Crystals; mp: 50-52 °C; specific optical rotation: +24.5 deg at 20 °C/D (concentration by volume= 1.0 g in 100 ml chloroform) /(1R)(3R)(alpha S)- Cyfluthrin/
Danger
H300: Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P263, P264, P270, P271, P273, P284, P301+P316, P304+P340, P308+P316, P316, P318, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H300+H330 (65.2%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P203, P260, P261, P263, P264, P270, P271, P273, P284, P301+P316, P304+P340, P308+P316, P316, P318, P320, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Hazard Traits - Dermatotoxicity; Developmental Toxicity; Endocrine Toxicity; Environmental tox; Neurotoxicity; Reproductive Toxicity; Respiratory Toxicity
Regulation (EC) No 396/2005 (amended)
Regulation (EC) No 396/2005 (amended)
Beta Cyfluthrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Cyfluthrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
03/31/EC, Reg. (EU) 2022/801, Reg. (EU) No 460/2014, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Combustible. See Chemical dangers Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. Risk of fire and explosion on contact with strong oxidants.
P - Antiparasitic products, insecticides and repellents
QP - Antiparasitic products, insecticides and repellents
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/
... Type II pyrethroids are a group of insecticides largely used in agriculture and public health. The nervous system is the main target for pyrethroids in insects and mammals. One notable form of toxicity associated with over exposure has been a facial cutaneous paraesthesia and irritation-related respiration symptoms including behavioral excitation mainly observed in workers spraying pyrethroids or in occupational settings. In acutely exposed rats, type II pyrethroids produce a severe syndrome characterized by salivation and choreoathetosis. Because many of the acute functional effects of type II pyrethoids can be associated with the neurotoxic effect on 5-hydroxytryptamine (5-HT) neurones, the objective of the present study was to examine whether deltamethrin, cyfluthrin and lambda-cyhalothrin administration results in changes of 5-HT content in rat brain. ... Rats were injected with either corn oil or pyrethroids (deltamethrin, 20 mg/kg per day, ip, for 6 days; cyfluthrin, 14 mg/kg per day, ip, for 6 days; lambda-cyhalothrin, 8 mg/kg per day, ip, for 6 days). The frontal cortex, hippocampus, midbrain and striatum were removed at 24 hours post treatment and were analysed for content of 5-HT and 5-HIAA using a HPLC method with electrochemical detection. ... A serotonin depleting effect was produced by these type II pyrethroids. The concentration of 5-HT and its metabolite 5-HIAA decreased in the brain regions from pyrethroid treated animals. Pyrethroids accelerated the turnover of 5-HT in midbrain and striatum areas. It is concluded that pyrethroids affect serotonin neurotransmission.
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読み込み中…
68359-37-5DTXSID5035957CHEMBL2104608CHEBI:403460 °C
1.50X10-10 mm Hg at 20 °C
negligible
Cyfluthrin appears as a viscous amber partly crystalline oil. Used as an insecticide.
Yellowish-brown liquid or colorless solid; [HSDB] Brown solid; [MSDSonline]
BROWN CRYSTALS WITH CHARACTERISTIC ODOUR.
Pyrethrins ... /are/ stable for long periods in water-based aerosols where ... emulsifiers give neutral water systems. /Pyrethrins/
Thermally stable @ room temp.
化学的特性In pure form this chemical may be colorless crystalline solid or powder. Commercial is a yellowish paste or viscous, yellowish-brown oil. Aromatic odor.
A skin, eye, and mucous membrane irritant; In human experiments, the threshold for upper respiratory tract irritation was 0.1 mg/m3; Common symptoms after overexposure in the workplace are stinging sensations of the skin and mucous membranes that begin 1-2 hours after contact and last for 1-2 days; Such symptoms are thought to be due to local action on sensitive nerves; [HSDB] Toxic by inhalation and ingestion; [eChemPortal: ESIS] A skin and eye irritant; [MSDSonline]
WHO; Toxicological evaluation of certain veterinary drug residues in food. WHO Food Additives Series 39. Cyfluthrin. Prepared for the forty-eighth meeting of the Joint FAO/WHO Expert Committee on Food Additives (JECFA), World Health Organization, Geneva (1997). The Committee concluded that the effects most relevant for the toxicological evaluation of cyfluthrin were those observed in the long-term study in rats fed the compound in the diet. The NOEL was 50 mg/kg in feed, equal to 2 mg/kg bw per day, on the basis of depression of body-weight gain. Using this NOEL and a safety factor of 100, the Committee established an ADI for cyfluthrin of 0-20 ug/kg bw. The Committee noted that the same value had been established by the JMPR in 1987.
Purdue University; National Pesticide Information Retrieval System, Cyfluthrin Fact Sheet No. 164 (1987)
Tolerances are established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2dimethyl-cyclopropane-carboxylate; CAS No. 68359-37-5) in or on the following raw agricultural commodities: [Table#6089]
A tolerance ... is established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; CAS Reg. No. 69359-37-5) in food commodities exposed to the insecticide during treatment of food-handling establishments where food and food products are held, processed, prepared, or served. Treatments may be made by general surface, spot, and/or crack and crevice applications.
A tolerance of ... is established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; CAS Reg. No. 68359-37-5) in feed commodities exposed to the insecticide during treatment of feed-handling establishments where feed and feed products are held, processed, prepared, or served. Treatments may be made by general surface, spot, and/or crack and crevice applications.
Tolerances with regional registration, as defined in section 180.1(n), are established for residues of cyfluthrin in or on the following raw agricultural commodities: [Table#6090]
New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128831; Type of Pesticide: Conventional - Insecticide; Use Site: Food use, ornamentals; Year: 1987.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Use powder, water spray, foam, carbon dioxide.
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give a slurry of activated charcoal in water to drink. Do NOT induce vomiting. Refer immediately for medical attention.
Keep in a well-ventilated room. Well closed. Separated from strong oxidants, strong acids and strong bases. Separated from food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.
Use carbon dioxide, foam, or dry chemical /on fires involving pyrethroids/. /Pyrethrum/
Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode. /Pyrethrum/
Extinguish fire using agent suitable for type of surrounding fire. /Pyrethrins/
PESTICIDE STORAGE: Store in a cool, dry place and away from open flame and extreme heat. Store in such a manner as to prevent cross contamination with other pesticides, fertilizers, food, and feed. Store in original container and out of the reach of children, preferably in locked storage area. Handle and open container in a manner as to prevent spillage. If container is leaking, invert container to prevent leakage. If the container is leaking or material spilled for any reason or cause, carefully dam up spilled material to prevent runoff. Refer to Precautionary Statements on /product/ label for hazards associated with the handling of this material. Do not walk through spilled material. ... /Baythroid XL/
Pyrethrins with piperonyl butoxide topical preparations should be stored in well-closed containers at a temperature less than 40 °C, preferably between 15-30 °C. /Pyrethrins/
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/
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: Pesticide wastes are acutely hazardous. Improper disposal of excess pesticide, spray mixture, or rinsate is a violation of Federal Law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. CONTAINER DISPOSAL - NON-REFILLABLE CONTAINER: Triple rinse (or equivalent). Then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or incineration or, if allowed by state and local authorities, by burning. If burned, stay out of smoke. CONTAINER DISPOSAL - RETURNABLE/REFILLABLE SEALED CONTAINER: Do not rinse container. Do not break seals. Replace the dust cover/cap and return container, intact to point of purchase. /Baythroid XL/
Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Ventilation. Do NOT let this chemical enter the environment. If solid: sweep spilled substance into sealable containers. If liquid: collect leaking liquid in sealable containers as far as possible. Absorb remaining liquid in dry sand or inert absorbent. Then store and dispose of according to local regulations.
Causes substantial but temporary eye injury. Do not get in eyes or on clothing. Wear protective eyewear (goggles or face shield). Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash before reuse. May be fatal if swallowed. Harmful if inhaled or absorbed through skin. Do not breathe vapors or spray mist. Prolonged or frequently repeated skin contact may cause allergic skin reactions in some individuals. /Baythroid XL/
User should: Wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughIy and change into clean clothing. /Baythroid XL/
Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this products concentrate. Do not reuse them. Follow manufacture's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Baythroid XL/
Agricultural Use Requirements: Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. ... Do not enter or allow worker entry into treated areas during the REI of 12 hours. 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: Chemical-resistant gloves, such as barrier laminate or viton; Shoes plus socks; Protective eyewear. /Baythion XL/
For more Preventive Measures (Complete) data for CYFLUTHRIN (16 total), please visit the HSDB record page.
Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)
/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/
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 ... were additive. /Pyrethrins/
At high doses, signs of poisoning attributable to cyfluthrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. As for other type 2 pyrethroids, cyfluthrin produces a severe syndrome characterized by salivation and choreoathetosis. (L863)
LC50 /Leuciscus idus/ (Golden orfe) 330.9 ng/L/96 hr /Conditions of bioassay not specified/
LC50 /Lepomis macrochirus/ (Bluegill sunfish) 28 ng/L/96 hr /Conditions of bioassay not specified/
LD50 /Coturnix/ (Japanese quail) oral >2,000 mg/kg
LC50; Species: Americamysis bahia (Opossum shrimp, age <24 hr); Conditions: saltwater, flow through; Concentration: 0.00242 ug/L for 96 hr (95% confidence interval: 0.00190-0.00316 ug/L) /92% purity/
For more Ecotoxicity Values (Complete) data for CYFLUTHRIN (16 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc range of 3,700-33,913(2) indicates that cyfluthrin is expected to have slight to no mobility in soil(SRC). Volatilization of cyfluthrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.90X10-8 atm-cu m/mole(SRC) derived from its vapor pressure, 1.50X10-10 mm Hg(3), and water solubility, 3.00X10-3 mg/L(3). Cyfluthrin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.50X10-10 mm Hg(3). Over 90% biodegradation was observed under anaerobic soil conditions during a 140 day incubation period(4). The initial products of cyfluthrin anaerobic biodegradation are 3-(2,2-dichlorovinyl)2,2-dimethylcyclopropancarboxcylic acid and 4-fluoro-3-phenoxybenzoic acid(4). Half-lives of 56-63 days, 7-90 days(5), and 116 days(6) have been reported in unspecified soil conditions and the metabolites are expected to undergo further degradation to carbon dioxide(5). Based on this data, biodegradation in soil is expected to be an important environmental fate process(SRC).
AQUATIC FATE: Based on a classification scheme(1), an experimetnal Koc rqange of 3,700-33,912(2), indicates that cyfluthrin 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 2.9X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 1.5X10-10 mm Hg(4), and water solubility, 3.0X10-3 mg/L(4). According to a classification scheme(5), an estimated BCF of 170(SRC), from its log Kow of 5.95(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC). A half-life of 16 hours in aqueous solution when irradiated with light at wavelengths >290 nm(8) suggests that photolysis is expected to be an important environmental fate process in water(SRC). Biodegradation half-lives of 56-63 days, 7-90 days(9) and 114 days(10) in unspecified soil conditions suggest that biodegration may be an important fate process in water(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyfluthrin, which has a vapor pressure of 1.5X10-10 mm Hg at 20 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase cyfluthrin may be removed from the air by wet or dry deposition(SRC). Photolysis is expected to be an important environmental fate process for cyfluthrin(SRC), based on an experimental half-life of 16 hours which was measured for cyfluthrin in aqueous solution, irradiated with light at environmental wavelengths >290 nm(3).
During a 5 year monitoring study conducted between April 1995 and March 2000 which tested 750 samples of domestic and imported agricultural products in the Hyogo Prefecture, Japan, cyfluthrin was detected at concns of <0.05 ug/g one time and a concn of <0.1 ug/g twice on domestic grapes(1). These detections totaled three out of a total of 106 tested samples(1).
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Inhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
A 484-kg lactating Holstein dairy cow (Bos taurus) was given 14C-cyfluthrin orally at a dose of 0.5 mg/kg bw after the evening milking each day for five consecutive days. Milk was collected in the morning and evening throughout the study. The cow was sacrificed on day 6 after initial administration, and blood, major organs, fatty tissue, and muscle were analysed for radiolabel. The maximum concentration of radioactivity in the milk was 0.079 mg/L cyfluthrin equivalents three days after initial dosing; the level then declined steadily. Of the radiolabel found in milk, 98% was on unmetabolized parent compound. The highest levels of residues were found in the liver (0.622 mg/kg), fat (0.195 mg/kg), and kidney (0.188 mg/kg); brain, skeletal muscle, and myocardium had the lowest levels, ranging from 0.015 to 0.040 mg/kg. Most of the radiolabel recovered in tissues was on unmetabolized parent compound. Heart and kidney also contained a metabolite identified as 4-fluoro-3-phenoxybenzenemethanol, and liver also contained 4-fluoro-3-phenoxybenzaldehyde.
Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
/AQUATIC SPECIES/ Cyfluthrin is extremely toxic to fish and aquatic organisms but is practically non-toxic to upland game birds and waterfowl.
/AQUATIC SPECIES/ The acute toxicities of four recently developed pyrethroid insecticides (bifenthrin, cyfluthrin, lambda cyhalothrin and tralomethrin) were experimentally compared to the acute toxicity of a first generation pyrethroid (permethrin), in static-flow, 48-hr bioassays with Daphnia magna and Ceriodaphnia dubia. The four new generation pyrethroids exhibited greater toxicity, with LC50s ranging from 0.15 to 1.04 ug/L for D. magna and 0.07 to 0.30 ug/L for C. dubia, in comparison to permethrin with LC50s of 1.25 ug/L for D. magna and 0.55 ug/L for C. dubia. Tralomethrin and cyfluthrin were most toxic to D. magna, with LC50s of 0.15 and 0.17 ug/L, respectively. C. dubia exhibited the greatest sensitivity to the pyrethroids, with an LC50 of 0.07 ug/L for bifenthrin. C. dubia was equally or more sensitive than D. magna to all of the insecticides.
/AQUATIC SPECIES/ Critical thermal maximum (CTMax) and minimum (CTMin) techniques were used to bioassay the effects of sublethal exposures of a synthetic pyrethroid, cyfluthrin, to 240 larval fathead minnows, Pimephales promelas. Fathead minnows were exposed for 24 hr to nominal concentrations of cyfluthrin with acetone as a carrier equal to approximately 20 and 70% of the 96-hr LC50. Exposure to cyfluthrin caused maximum decreases of 3.3 °C below median heat tolerance of controls (34.4 °C) and a 5.6 °C increase in median cold tolerance above controls (5.9 °C). At the highest concentrations of cyfluthrin tested, the zone of temperature tolerance was reduced by 30%. Concentrations of cyfluthrin that caused these effects were as low as 170 parts per trillion.
/AQUATIC SPECIES/ ... All eight isomers of cypermethrin and cyfluthrin were completely separated on two chained Chirex 00G-3019-DO columns. Great differences were found between enantiomers in the acute toxicity to aquatic invertebrates Ceriodaphnia dubia or Daphnia magna. ... In cypermethrin or cyfluthrin, two of the eight isomers, 1R-cis-alphaS and 1R-trans-alphaS, contributed for almost all the toxicity in the racemate, while the other six enantiomers were inactive. These results suggest that significant enantioselectivity occurs for pyrethroids in aquatic toxicity, and such enantiomeric differences must be considered when evaluating ecological effects of pyrethroid insecticides.
For more Ecotoxicity Excerpts (Complete) data for CYFLUTHRIN (11 total), please visit the HSDB record page.
Tolerances are established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2dimethyl-cyclopropane-carboxylate; CAS No. 68359-37-5) in or on the following raw agricultural commodities: [Table#6089]
A tolerance ... is established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; CAS Reg. No. 69359-37-5) in food commodities exposed to the insecticide during treatment of food-handling establishments where food and food products are held, processed, prepared, or served. Treatments may be made by general surface, spot, and/or crack and crevice applications.
A tolerance of ... is established for residues of the insecticide cyfluthrin (cyano(4-fluoro-3-phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate; CAS Reg. No. 68359-37-5) in feed commodities exposed to the insecticide during treatment of feed-handling establishments where feed and feed products are held, processed, prepared, or served. Treatments may be made by general surface, spot, and/or crack and crevice applications.
Tolerances with regional registration, as defined in section 180.1(n), are established for residues of cyfluthrin in or on the following raw agricultural commodities: [Table#6090]
New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128831; Type of Pesticide: Conventional - Insecticide; Use Site: Food use, ornamentals; Year: 1987.
... Since the type II pyrethroids deltamethrin and cypermethrin, but not the type I pyrethroid cismethrin act on chloride channels, this could contribute to the bimodal nature of pyrethroid poisoning syndromes. ... Excised inside-out membrane patches from differentiated mouse neuroblastoma cells were used, and mean channel open probabilities calculated. For single dosing at 10 uM, bioallethrin, beta-cyfluthrin, cypermethrin, deltamethrin, and fenpropathrin were all found to significantly decrease open channel probability (p < 0.05). Bifenthrin, bioresmethrin, cispermethrin, cisresmethrin, cyfluthrin isomers 2 and 4, lambda-cyhalothrin, esfenvalerate, and tefluthrin, did not significantly alter open channel probability (p > 0.05). Since the type II pyrethroids, esfenvalerate, and lambda-cyhalothrin were ineffective, /one/ must conclude that actions at the chloride ion channel target cannot in themselves account for the differences between the two types of poisoning syndrome. Sequential dosing with type II pyrethroids caused no further chloride ion channel closure. The type I pyrethroid cisresmethrin did however prevent a subsequent effect by the mixed type pyrethroid fenpropathrin. In contrast, the type I pyrethroid cispermethrin did not prevent a subsequent effect due to the type II pyrethroid deltamethrin. The difference in effect may be the result of differences in potency, as deltamethrin had a greater effect than fenpropathrin. It therefore appears clear that in some combinations the type I and type II pyrethroids can compete and may bind to the same chloride channel target site.
For more Mechanism of Action (Complete) data for CYFLUTHRIN (7 total), please visit the HSDB record page.
Nine male volunteers were exposed to the pyrethroid insecticide cyfluthrin. ... The mean half-lives were 6.9 hr for cis-3-(2,2-dichlorovinyl)-2,2-dimethylycyclopropane carboxylic acid (cis-DCCA), 6.2 hr for trans- 3-(2,2-dichlorovinyl)-2,2-dimethylycyclopropane carboxylic acid (trans-DCCA) and 5.3 hr for 4-fluoro-3-phenoxybenzoic acid. The mean trans-:cis-DCCA ratio was 1.9 for the time course as well as for each subject. ...
... A cyfluthrin elimination experiment showed that cyfluthrin metabolites are eliminated following first-order kinetics (t 1/2 = 6.4 hr )...
Nine male volunteers were exposed to the pyrethroid insecticide cyfluthrin. ... The main urinary cyfluthrin metabolites, cis-/trans-3-(2,2-dichlorovinyl)-2,2-dimethylycyclopropane carboxylic acid (DCCA) and 4-fluoro-3-phenoxybenzoic acid (FPBA), were determined. The limit of detection (LOD) for all metabolites was 0.0025 ug in an urine sample of 5 mL (0.5 ug/L). After inhalative exposure of 40 ug cyfluthrin/cu m air for 60 min, the amount of metabolites in urine collected in the first 2 hr after exposure was less than the LOD, namely 0.14 ug for cis-DCCA, 0.15-0.28 ug for trans-DCCA and 0.12-0.23 ug for FPBA. Of the metabolites, 93% was excreted within the first 24 hr (peak excretion rates between 0.5 and 3 hr) after inhalative exposure of 160 ug/cu m. ... The amount of metabolites in urine depends on the applied dose, on the exposure time and shows interindividual differences.
Eight hours after oral administration of 14C-labelled cyfluthrin at a dose of 10 mg/kg bw to three male Sprague-Dawley rats, about 60% of the labelled cyfluthrin was eliminated in the urine in conjugated forms. Conjugates of 4'-hydroxy-3-phenoxyfluorobenzoic acid (50%) were identified; a second major metabolite was identified after hydrochloric acid hydrolysis as a conjugate of 3-phenoxy-4-fluorohippuric acid (40%). These metabolites represented 33 and 27% of the administered radiolabel, respectively. A glycine conjugate constituted 2.5% of the conjugated metabolites.
In another study ... , four groups of five male and five female rats received 14C-cyfluthrin ... . The initial step in cyfluthrin biotransformation was ester hydrolysis, giving a 3-phenoxy-4-fluorobenzyl alcohol intermediate and the permethric acid fraction. The metabolism of permethric acid has been well established in the rat in studies with chemically similar pyrethroids. After ester hydrolysis, the 3-phenoxy-4-fluorobenzyl alcohol moiety was oxidized to the free metabolite 3-phenoxy-4-fluorobenzoic acid. This metabolite can then either be conjugated with glycine to form 3-phenoxy-4-fluorohippuric acid (a minor metabolite constituting < 3% of the recovered urinary radiolabel, dependent on neither sex nor dose) or hydroxylated to give 4'-hydroxy-3-phenoxy-4-fluorobenzoic acid (conjugates of which account for 41-50% of the total urinary radiolabel recovered from rats given one or multiple doses of cyfluthrin at 0.5 mg/kg bw). Females tended to excrete more of this metabolite as the free form in the faeces than did males. Males and females at the high dose (10 mg/kg bw) excreted about 35% of the administered dose as conjugates of 4'-hydroxy-3-phenoxy-4-fluorobenzoic acid, whereas females excreted about 5% more than males as the free metabolite. After repeated oral doses of 0.5 mg/kg bw for 14 days, 12-16% of labelled metabolite was found in the faeces as cyfluthrin, whereas < 1% was found when single oral doses were administered. After a single high dose of 10 mg/kg bw, 17-19% was recovered in the faeces as parent compound. The authors concluded that the metabolism of cyfluthrin is slightly dose-dependent.
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/
For more Metabolism/Metabolites (Complete) data for CYFLUTHRIN (8 total), please visit the HSDB record page.
The initial step in cyfluthrin biotransformation is ester hydrolysis, giving a 3-phenoxy-4-fluorobenzyl alcohol intermediate and the permethric acid fraction. After ester hydrolysis, the 3-phenoxy-4-fluorobenzyl alcohol moiety is oxidized to the free metabolite 3-phenoxy-4-fluorobenzoic acid. This metabolite can then either be conjugated with glycine to form 3-phenoxy-4-fluorohippuric acid or hydroxylated to give 4'-hydroxy-3-phenoxy-4-fluorobenzoic acid. The metabolites as well as a small pert of the unmetabolized compound are excreted in the urine in the feces. (L857, A562)
Nine male volunteers were exposed to the pyrethroid insecticide cyfluthrin. The study was performed in an exposure room, where an aerosol containing cyfluthrin was sprayed to obtain atmospheres with mean cyfluthrin concentrations of 160 and 40 ug/cu m. Four volunteers were exposed for 10, 30 and 60 min at 160 ug/cu m and another five volunteers were exposed for 60 min at 40 ug/cu m. For 160 ug/cu m exposure urine samples were collected before and immediately after exposure as well as for the periods 1-2, 2-3, 3-4, 4-5, 5-6, 6-12 and 12-24 hr after exposure. For 40 ug/cu m exposure urine samples were collected before and 2 hr after exposure. ... Of the metabolites, 93% was excreted within the first 24 hr (peak excretion rates between 0.5 and 3 hr) after inhalative exposure of 160 ug/cu m. ... The amount of metabolites in urine depends on the applied dose, on the exposure time and shows interindividual differences.
14C derived from the alcohol moiety was rapidly and completely excreted into urine and feces after single oral administration of 14C-alcohol labeled preparation to rats at 0.5 and 10 mg/kg, 55-70 and 25-35% of the dose being excreted into urine and feces, respectively. Excretion of 14C into bile was about 34%. The fat and sciatic nerve showed relatively higher 14C tissue residues.
The influence of the formulation vehicle on the rate of absorption of cyfluthrin was studied in groups of 14 fasted male Wistar rats given single doses by gavage of 10 mg/kg bw dissolved in either polyethylene glycol (PEG) 400 or a Cremophor EL:water emulsion. Two rats from each group were killed 0.5, 1, 2, 4, 6, 16, and 24 hr after treatment. The concentrations of cyfluthrin and its respective enantiomers were determined in the blood and stomach. When the compound was emulsified in the Cremophor EL:water solution, absorption was rapid; the cis isomer was that most frequently detected within 30 min after treatment. Maximum peak blood concentrations occurred within 1 hr of treatment. Cyfluthrin emulsified in PEG 400 was not detected until 4 hr after administration, and peak blood levels were observed only 6 hr after treatment. Examination of the stomach contents revealed a larger quantity of cyfluthrin in the stomachs of rats treated with the drug in a PEG 400 emulsion
Four groups of 30 male and 24 female Mura:SPRA (SPF 68 Han) rats received 14C-radiolabelled cyfluthrin as either oral doses of 0.5 or 10 mg/kg bw or iv or intraduodenal doses of 0.5 mg/kg bw. Another group received unlabelled cyfluthrin orally once a day for 14 consecutive days, followed by a single oral dose of 0.5 mg/kg bw 14C-cyfluthrin. Excreta, organs, tissues, and blood samples were collected at several intervals and assayed for radiolabel. After oral administration by any schedule, up to 80% of the labelled cyfluthrin was effectively absorbed by females and about 90% by males. ... Less than 2% of radiolabelled drug was present 48 hr after oral administration. No significant pulmonary excretion pathway exists, as < 0.001% was detected in the expired gaseous phase as 14CO21. About 98-99% of the orally administered dose was readily available for renal and fecal excretion ... . Males excreted two to three times more in the urine than in the feces, whereas the renal:fecal excretion ratio in females was 1.2-1.7:1 after oral administration. Consequently, the area under the curve (AUC) is two times larger for females than males. Forty-eight hours after the iv injection, 93-95% of the dose was excreted, with a renal:fecal excretion ratio of 2.9:1 in males and 2.3:1 in females. Therefore, excretion depends somewhat on the route of administration and on sex. ... The residues found in the organs and tissues were influenced by the route of administration, as the mean relative concentration of cyfluthrin in the bodies of males and females at sacrifice was lower after oral administration (0.013) than after intravenous injection (0.06). Female rats had higher plasma concentrations after oral administration of the single high or low dose; 48 hr after administration, lower concentrations were detected in the bone and muscle of animals of each sex and in the testes of males rats. The sciatic nerve showed a similar relative concentration value, which may explain the toxic effects observed on the peripheral nervous system. Higher concentrations were detected in the spleen, adrenal glands, liver, and plasma of both males and females and in the ovaries. The renal fatty tissue concentration was about seven times higher after either oral or intravenous administration, whereas the mean concentration in brain was significantly lower ( p = 0.0006-0.006)...
For more Absorption, Distribution and Excretion (Complete) data for CYFLUTHRIN (9 total), please visit the HSDB record page.
Used as an agricultural insecticide; [Merck Index] Used as a veterinary medication; [HSDB]
Farming (Pesticides) [Category: Industry]
For cyfluthrin (USEPA/OPP Pesticide Code: 128831) 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./
Agricultural insecticide
Insecticide effective against Lepidoptera, Coleoptera, Hemiptera and Homoptera ... also against migratory locusts and grasshoppers; and in animal health
MEDICATION (Vet)
ANT & ROACH KILLER PUMP SPRAY B: Active Ingredients 0.30% Sodium o-phenylphenate and 0.05% beta-cyfluthrin
BAYTHROID XL: Active Ingredient 12.7% beta-cyfluthrin
BETA-CYFLUTHRIN 0.0015% RTU INSECTICIDE: Active Ingredient 0.0015% beta-cyfluthrin
BETA-CYFLUTHRIN 0.38% CONCENTRATE INSECTICIDE: Active Ingredient 0.38% beta-cyfluthrin
For more Formulations/Preparations (Complete) data for CYFLUTHRIN (20 total), please visit the HSDB record page.
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
Veterinary Drug -> INSECTICIDE -> JECFA Functional Classes
The WHO Recommended Classification of Pesticides by Hazard identifies Cyfluthrin and beta-Cyfluthrin (technical grade) as Class II: moderately hazardous; Main Use: insecticide.
RESTRICTED USE PESTICIDE due to toxicity to fish and aquatic organisms. For retail sale to and use only by Certified Applicators or persons under their direct supervision and only for those uses covered by the Certified Applicator's certification. /Baythroid XL/
Synthetic pyrethroid insecticide. Commercial product is mixture of 8 isomers, the (1R)-isomers primarily responsible for the bioactivity.
The Compendium of Pesticide Common Names lists CAS no. 68359-37-5 as beta-cyfluthrin, noting that the unresolved isomeric mixture of this substance has the ISO common name cyfluthrin.
For more General Manufacturing Information (Complete) data for CYFLUTHRIN (9 total), please visit the HSDB record page.
用途ピレスロイド系殺虫剤
用途シフルトリン試験用標準品。
説明Cyfluthrin is a pyrethroid insecticide and a modulator of voltage-gated sodium channels (Nav). It slowly activates rat recombinant Nav1.8 channels, delays inactivation by longer than 40 ms, and induces persistent tail currents in channels expressed in X. laevis oocytes. It also decreases the mean burst rate in rat primary neurons (IC50 = 0.99 μM, respectively). Cyfluthrin is toxic to various insects, including A. melinus, G. ashmeadi, E. eremicus, and E. formosa (LC50s = 7, 67, 96, and 63 ng/ml, respectively) and the A. sinensis mosquito (LC50 = 0.446 ppm). It is also toxic to A. mellifera honeybees (LD50 = 0.22 ppm), affecting locomotor activity and wing fanning behavior with an increase in the mean bout duration of time spent upside down, indicating disruption of the righting reflex, and a decrease in wing fanning behavior when administered at a dose of 10 ng/bee. Formulations containing cyfluthrin have been used for the control of insects in agriculture and for non-commercial purposes.
使用Cyfluthrin is used to control a wide range of insects, especially Lepidoptera, in cereals, fruit, vegetables and cotton. It is also used against migratory locusts and grasshoppers, in stored products, in public health situations and in animal health.
一般的な説明A viscous amber partly crystalline oil. Used as an insecticide.
定義ChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.