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Name:	Cypermethrin
CAS No:	52315-07-8
CAS No:	71697-59-1

PRODUCT DESCRIPTION

【Name】: Cypermethrin

【CAS Registry number】: 52315-07-8;71697-59-1

【Synonyms】: Cyano-3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
(+/-)-alpha-cyano-3-phenoxybenzyl (+/-)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl ester
Fendona
Flectron
FMC 30980
Folcord
Imperator
KafilSuper
Kefil Super
NRDC 149
Polytrin
PP 383
Ripcord
(RS)-alpha-Cyano-3-Phenoxybenzyl (1RS)-cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Siperin
Supermethrin
Ustaad
zeta-cypermethrin
Alpha-cyano-3-phenoxy-benzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
alpha-Cyano(3-phenoxyphenyl)methyl (+-)cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Agrothrin
Ammo
Arrivo
Barricade
beta-cypermethrin
CCN52
Chinmix
Cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate
Cyano(3-phenoxyphenyl)methyl (+/-)-cis/trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Cymbush
Cymbush 2E
Cymbush 3E
Cymperator
Cynoff
Cypercare
Cypercopal
Cyperkill
Cypermar
(RS)-a-cyano-3-phenoxybenzyl(1RS,3RS
cyano(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
95% cypermethrin TC
(RS)-a-cyano-3-phenoxybenzyl (1RS,3RS
1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(RS)-a-cyano-3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Cyano-3-phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate

【EINECS(EC#)】: 257-842-9

【Molecular Formula】: C22H19Cl2NO3 (Products with the same molecular formula)

【Molecular Weight】: 416.3

【Inchi】: InChI=1/C22H19Cl2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3

【Canonical SMILES】: CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

【MOL File】
52315-07-8;71697-59-1.mol

Chemical and Physical Properties

【Appearance】: Viscous semisolid

【Density】: 1.12

【Melting Point】: 60-80℃

【Boiling Point】: 170-195℃

【Refractive Index】: n20/D 1.57

【Flash Point】: 100 °C

【Water】: insoluble

【Solubilities】: In acetone, chloroform, cyclohexanone, xylene greater than 450, ethanol 337, hexane 103 (all in g/l at 20 deg C).
Soluble in methanol and methylene dichloride
In water, 4X10-3 mg/l @ 20 deg C

【Color/Form】: Viscous semi-solid
Pure isomers; colorless crystals

【Stability】: Stable. Incompatible with bases, strong oxidizing agents.

【Storage temp】: −20°C

【Computed Properties】: Molecular Weight:416.29716 [g/mol]
Molecular Formula:C₂₂H₁₉Cl₂NO₃
XLogP3:6
H-Bond Donor:0
H-Bond Acceptor:4
Rotatable Bond Count:7
Exact Mass:415.074199
MonoIsotopic Mass:415.074199
Topological Polar Surface Area:59.3
Heavy Atom Count:28
Formal Charge:0
Complexity:643
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:3
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:7.6
Conformer Sampling RMSD:1.4
CID Conformer Count:217

Safety and Handling

【Hazard Codes】: Xn:Harmful;N:Dangerousfortheenvironment;

【Risk Statements】: R22;R37/38;R43;R50/53

【Safety Statements 】: S2;S36/37/39;S60;S61

【HazardClass】: 6.1(b)

【PackingGroup 】: III

【Skin, Eye, and Respiratory Irritations】: Immediately irritating to the eye. /Pyrethrins/
The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes.

【Cleanup Methods】: Spillages of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: these should be removed by vacuum cleaning, or by dissolving them in water, or other solvent in the factory environment. /Pesticides/

【Transport】: UN 2810 6.1/PG 3

【Fire Fighting Procedures】: 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/

【Formulations/Preparations】: USEPA/OPP Pesticide Code 109-702; Trade Names: Cymbush 2E Insecticide , Cymbush 3E insecticide, Barricade, Folcord, Imperator, Kafil super, PP 383, Siperin, Flectron, Ustaad, Cyrux, WL 43467.
25%, 10%, and 5% emulsifiable concentrates and 1.5% ULV; also 400 g/l.
Tech. grade is 90& pure
Emulsifiable concentrate; granules; wettable powder; ultra-low volume liquid.
Mixtures: (cypermethrin +) monocrotophos; phefenofos; sulfur; chlorofenvinphos

【Reactivities and Incompatibilities】: Incompatibility: Strong oxidizers. /Pyrethrins/
... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/

【Other Preventative Measures】: SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Skin that becomes contaminated with /pyrethrum/ should be promptly washed or showered with soap or mild detergent and water. /Pyrethrum/
Clothing contaminated with /pyrethrum/ should be placed in closed containers for storage until provision is made for the removal of /pyrethrum/ from the clothing. /Pyrethrum/
Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail or need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. /Pyrethrum/
Employees who handle /pyrethrum/ ... should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Pyrethrum/
Avoid contact with skin. Keep out of any body of water. Do not contaminate water by cleaning of equipment or disposal of waste. Do not reuse empty container. Destroy it by perforating or crushing. /Pyrethrum/
Workers should wash: Promptly when skin becomes contaminated. /Pyrethrins/
Work clothing should be changed daily: If it is reasonably probable that the clothing may be contaminated. /Pyrethrins/
Remove clothing: Promptly if it is non-impervious clothing that becomes contaminated. /Pyrethrins/
If /pyrethrins/ are not involved in a fire: keep /pyrethrins/ out of water sources and sewers. Build dikes to contain flow as necessary. /Pyrethrins/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

【Protective Equipment and Clothing】: Wear protective clothing, gloves, and face shield when handling concentrate or spraying.
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 appropriate equipment to prevent: Repeated or prolonged skin contact. /Pyrethrum and pyrethrins/
Wear eye protection to prevent: Reasonable probability of eye contact. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 50 mg/cu m: Respirator Classes: Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. Any supplied-air respirator. May require eye protection. Any self-contained breathing apparatus. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 125 mg/cu m: Respirator Classes: Any supplied-air respirator operated in a continuous flow mode. May require eye protection. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 250 mg/cu m: Respirator Classes: Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece. Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 5,000 mg/cu m: Respirator Class: Any supplied-air respirator with a full facepiece and operated in a pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Classes: Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode. Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Classes: Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus. /Pyrethrins/

【Octanol/Water Partition Coefficient】: log Kow = 6.60

【Disposal Methods】: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incinerate cypermethrin in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert (May 1985)).
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/

Use and Manufacturing

【Use and Manufacturing】: Methods of Manufacturing

Prepared from 3-phenoxybenzaldehyde and 3-(2,2-dichlorovinyl)2,2-dimethylcyclopropane carboxylic acid (esterification)

Consumption Patterns

In 1992, the estimated annual agricultural application of cypermethrin in the United States was 98 metric tons.

Biomedical Effects and Toxicity

【Pharmacological Action】: - Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

【Therapeutic Uses】: MEDICATION (VET): ectoparasiticide
Pyrethrins with piperonyl butoxide are used for topical treatment of pediculosis(lice infestations). Combinations of pyrethrins with piperonyl butoxide are not effective for treatment of scabies (mite infestations). Although there are no well-controlled comparative studies, many clinicians consider 1% lindane to be pediculicide of choice. However, some clinicians recommend use of pyrethrins with piperonyl butoxide, esp in infants, young children, & pregnant or lactating women ... . If used correctly, 1-3 treatments ... are usually 100% effective ... Oil based (eg, petroleum distillate) combinations ... produce the quickest results. ... For treatment of pediculosis, enough gel, shampoo, or solution ... should be applied to cover affected hair & adjacent areas ... After 10 min, hair is ... washed thoroughly ... treatment should be repeated after 7-10 days to kill any newly hatched lice. /Pyrethrins/

【Biomedical Effects and Toxicity】: Dermal exposure to cypermethrin during spray application at up to 46 mg/hr led to an estimation that approximately 3% was absorbed.
Exposure to cypermethrin & its absorption during aerial spraying of an ultra low volume formulation were studies. A contract pilot & mixer/loader at each of two commercial cotton farms in Mississippi were monitored for dermal exposure to cypermethrin during 12 aerial spray applications. Each operation consisted of 1 mixing/loading operation & 1 application of 50 gal of dilute spray soln for about 30 min. Three volunteer mixer/loaders collected their total urine output for 24 hr periods from 1 or 2 days before to 6 days after exposure. Absorption of cypermethrin was evaluated by determining cypermethrin urinary metabolites. All mixer/loaders wore protective equipment. Total potential & actual dermal exposures were estimated. Avg potential exposures (protected & exposed skin) were 1.07 & 10.5 mg/8 hr day (mg/day) for pilots & mixer/loaders, respectively. Actual skin exposures averaged 0.67 mg/day for pilots & 2.43 mg/day for mixer/loaders. 67% of the total potential exposures to pilots occurred on the hands. For the mixer/loaders, exposure involved primarily the arms, trunk, & hands, amounting to 37, 24, & 17% of total exposure, respectively. Absorption by mixer/loaders determined from analyses of urinary metabolites amounted to 46 to 78 ug cypermethrin equivalents per 3 mixed loads & per 12 simulated mixed loads. /It was/ concluded that exposure of pilots & mixer/loaders during aerial application of ultra low volumes is minimal. Only a small proportion of the cypermethrin that contacts the skin is absorbed.
1. Dose excretion studies with cypermethrin (as a 1:1 cis/trans mixture) & alphacypermethrin (1 of the 2 disastereoisomer pairs which constitute cis cypermethrin) were carried out with, in each case, 2 volunteers/dose level. The studies included (a) single oral alphacypermethrin doses of 0.25 mg, 0.50 mg & 0.75 mg followed by repeated alphacypermethrin doses at the same levels, daily for 5 days, (b) repeated oral cypermethrin doses of 0.25 mg, 0.75 mg & 1.5 mg daily for 5 days, & (c) a single dermal application of 25 mg cypermethrin to the forearm. Urine was monitored for the free & conjugated 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid before & after dosing. 2. Metab & rate of excretion of a single oral dose of alphacypermethrin was similar to that of cis cypermethrin, on average, 43% of the dose was excreted as the cyclopropanecarboxylic acid in the first 24 hr urine. There was no incr in urinary metabolite excretion when alphacypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 49% of the dose as the cyclopropanecarboxylic acid in the subsequent 24 hr periods after dosing. 3. There was no incr in the urinary cyclopropanecarboxylic acid excretion when cypermethrin was admin as a repeated oral dose. Subjects excreted, on average, 72% of the trans isomer dose & 45% of the cis isomer dose respectively in the subsequent 24 hr periods after dosing. 4. Approx 0.1% of the applied dermal dose of 25 mg cypermethrin was excreted within 72 hr as the urinary cyclopropanecarboxylic acid. No conclusions can be drawn from such urinary excretion data as to the concn of cypermethrin & its metabolites in the skin or other organs, or the possibility of other routes of metab or excretion.
/PYRETHROIDS/ READILY PENETRATE INSECT CUTICLE AS SHOWN BY TOPICAL LD50 TO PERIPLANETA (COCKROACH) ... /PYRETHROIDS/
WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/ [MIYAMOTO J; ENVIRON HEALTH PERSPECT 14: 15-28 (1976)] PubMed Abstract
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/
Elimination of radioactivity was measured in male Swiss-Webster mice, dosed once orally with cis- or trans- cypermethrin, C-labeled in either the benzyl (8 mg/kg bw) or cyclopropyl (7 mg/kg bw) moiety. The C-benzyl-dosed mice eliminated 22% & 34% of the admin dose of cis-isomer in the urine & feces, respectively, in 1 day; values for the trans-isomer were 41% & 16%, respectively. The C-cyclopropyl-dosed mice eliminated 20% of the admin dose of cis-isomer in the urine & 50% in the feces in 1 day; the values for the trans-isomer were 55% & 16%, respectively. Thus, radioactivity from the trans-isomer was mainly eliminated in the urine & that from the cis-isomer in the feces. The C-benzyl-treated mice were killed 1, 3, or 8 days after dosing; the C-cyclopropyl-treated mice, 3 days after dosing. Residues of radioactivity from both labels, 3 days after dosing, were low in all tissues except for the fat. The sequence of the residues in different organs was fat >liver =kidneys >blood =muscle >brain. Residues fell rapidly during the C-benzyl study, with the exception of the residues derived from the cis-isomer in fat, which did not decr during the study period. However, in a further study, radioactivity was measured in fat samples from 10 male mice taken up to 42 days after a single oral dose of approx 8.8 mg/kg bw (C-benzyl)-cis-cypermethrin. The residue was eliminated exponentially with a half-life of 13.1 (3.6-18.4) days. At 8 & 22 days after dosing, approx 90% of the radioactivity present in 2 pooled fat samples was attributable to unchanged cis-cypermethrin.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 5,800 to 160,000(2), indicate that cypermethrin is expected to be immobile in soil(SRC). Volatilization of cypermethrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 3.1X10-9 mm Hg(2), and water solubility, 4.0X10-3 mg/l(3). Cypermethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). The photodegradation of the cis- and trans-isomers of cypermethrin was studied by exposing various soil surface applications to sunlight for 7-10 days(4); half-lives on soil surfaces exposed to sunlight ranged from 0.6-1.9 days while half-lives on dark soil were >7 days(4). Cypermethrin degrades rapidly in soil under aerobic conditions(5). For example, the half-lives were 4.1 to 17.6 days for trans-cypermethrin and 12.5 to 56.4 days for the cis-cypermethrin under aerobic conditions in an incubated soil(5). Using a standardized soil test under laboratory conditions, the persistence half-life of cypermethrin was determined to be 21 days(6); however, when formulated with various sawdusts the half-life increased to 30-110 days(6). In a field persistence study conducted in India (max temperatures of 30.7-34.7 deg C) at applications of 75-150 g cypermethrin/ha, cypermethrin residues did not persist past 45 days (initial half-lives of about 3 days)(7). After spray applications in an orchard, the half-life of cypermethrin on vegetation under pear and apricot trees ranged from 14-17 days(8); soil contained no detectable cypermethrin after 100-120 days(8). After spraying wheat herbage, cypermethrin residues fell to 50% after 1 day and to 5% after 27 days(9).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 5,800 to 160,000(2), indicate that cypermethrin is expected to adsorb to suspended solids and sediment(SRC). In a pond experiment, surface applications of cypermethrin gradually partitioned to sediment with sediment concns exceeding surface and subsurface water concns after 13 days(3); in another pond experiment, dispersion of surface applications to subsurface water and sediment was very slow(3); however, after 4 wks, the concn in the sediment exceeded the water concns(3). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 4.2X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 3.1X10-9 mm Hg(2), and water solubility, 4.0X10-3 mg/l(5). According to a classification scheme(6), a BCF of 420 in golden ide fish (Leuciscus idus melanotus)(7) and 430 in rainbow trout (Oncorhynchus mykiss)(8), suggests the potential for bioconcentration in aquatic organisms is high(SRC). The aqueous hydrolysis half-life of cypermethrin in sterile water-ethanol (99:1) phosphate buffers at 25 deg C was determined to be 99, 69, 63, and 50 weeks at pHs of 4.5, 6, 7, and 8, respectively(9). In a photomineralization study using a UV light (>290 nm), 30.2% of initial cypermethrin was mineralized to CO2 during a 17-hr exposure period(7). The photodegradation of the cis- and trans-isomers of cypermethrin was studied by exposing various aqueous solutions to sunlight for 7-10 days; the half-lives in distilled water solution were 2.6-3.6 days in sunlight and >10 days in dark controls(10); the half-lives in river and seawater were 0.6-1.0 days and >10 days in dark controls(10). Cypermethrin degrades rapidly in soil under aerobic conditions(11). For example, in an incubated soil, the half-lives were 4.1 to 17.6 days for trans-cypermethrin and 12.5 to 56.4 days for the cis-cypermethrin under aerobic conditions(11). Cypermethrin should also degrade rapidly in aqueous systems(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cypermethrin, which has a vapor pressure of 3.1X10-9 mm Hg at 20 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere(SRC). Particulate-phase cypermethrin may be removed from the air by wet and dry deposition(SRC).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Use and Manufacturing

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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