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Flucythrinate

HCID 50980
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Basic information

CAS
70124-77-5
Standard SMILES
CC(C)C(C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1)c1ccc(OC(F)F)cc1
InChIKey
GBIHOLCMZGAKNG-UHFFFAOYSA-N
Molecular formula
C26H23F2NO4
Average molar mass
451.5 g/mol
Monoisotopic mass
451.15951466

Overview

Flucythrinate is a synthetic pyrethroid used to control insect pests in apples, cabbage, field corn, head lettuce, and pears, and to control Heliothis spp. in cotton, which is its primary use. It is available in emulsifiable concentrate, water-dispersible granules and wettable powder formulations. The AASTAR product also contains phorate, and it may also be found in formulation with chlorpyrifos, dimethoate, methomyl, or phenthoate. A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. Insects with certain mutations in their sodium channel gene may be resistant to pyrethroid insecticides. (L811, L708, L883)

Names & identifiers

Preferred name
Flucythrinate
IUPAC
[cyano-(3-phenoxyphenyl)methyl] 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoate
English name
FLUCYTHRINATE
Molecular formula
C26H23F2NO4
Molecular weight
451.47

Names & synonyms

FLUCYTHRINATE70124-77-5FluorocythrinCyBoltPay OffCythrinFunchiong jujrStock GuardAC 22270557D0GAO3RXcyano(3-phenoxyphenyl)methyl 2-(4-(difluoromethoxy)phenyl)-3-methylbutanoateBenzeneacetic acid, 4-(difluoromethoxy)-alpha-(1-methylethyl)-, cyano(3-phenoxyphenyl)methyl ester
Show more names
FLUENTPAY-OFFGuardinac222705guardianNSC68816NSC 68816
4-(Difluoromethoxy)-alpha-(1-methylethyl)benzeneacetic acid cyano(3-phenoxy-phenyl)methyl esterDTXSID0022301Cyano(3-phenoxyphenyl)methyl 2-(4-(difluoromethoxy)phenyl)-3-methylbutyrateCyano(3-phenoxyphenyl)methyl 2-[4-(difluoromethoxy)phenyl]-3-methylbutanoateCHEBI:34763AC-222705RefChem:140814DTXCID20209134

Database identifiers

CAS
70124-77-5
PubChem CID
50980
DTXSID

Properties

Computed structural propertiesFilling in

XLogP
6.2
Topological polar surface area
68.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
10
Heavy atoms
33
Formal charge
0
Complexity
650

Experimental & physicochemical properties

Pesticides · 4 items

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Pyrethrins/Pyrethroids

Pesticide (Flucythrinate) -> USDA PDB

LogP · 2 items

log Kow = 6.20

5.55

Density1.189 at 22 °C
Color/FormViscous liquid
Solubility · 2 items

In acetone >820, xylene 1,810, n-propanol >780, corn oil > 560, cottonseed oil >300, soya bean oil >300, hexane 90 (all in g/L, 21 °C).

In water, 0.06 mg/L at 25 °C

Boiling Point108 °C at 0.35 mm Hg
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides and hydrogen fluoride/
Vapor Pressure · 2 items

0.00000001 [mmHg]

8.7X10-9 mm Hg at 25 °C

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H226 (71.4%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P317, P319, P320, P321, P330, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 147 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information2002/2076
Fire Potential/Pyrethrins/ ... burn with difficulty. /Pyrethrins/
Hazards SummaryA synthetic pyrethroid; [Merck Index] Contact with skin causes delayed paresthesias; [HSDB] May cause irritation; May cause skin and respiratory sensitization after prolonged contact; [MSDSonline] See Pyrethrum.
Special Reports · 1 item

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.

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Flucythrinate is found on List B. Case No: 2290; Pesticide type: Insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): (+-)-flucythrinate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Chemistry & industry

Pharmacology

ATC CodeQP - Antiparasitic products, insecticides and repellents
Mechanism of Action · 5 items

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.

Metabolism/Metabolites · 6 items

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/

Related reactions

7 records
New reaction record
HRID 354735 reaction equation
HRID 354735As productuspto-grants-1983_03
HRID 666406 reaction equation
HRID 666406As productTraining data from https://doi.org/10.1039/C8SC04228D (3/10)
HRID 1074898 reaction equation
HRID 1074898As productuspto-grants-1983_07
HRID 1127864 reaction equation
HRID 1127864As productTraining data from https://doi.org/10.1039/C8SC04228D (7/10)
HRID 1732901 reaction equation
HRID 1732901As productuspto-grants-1980_12
HRID 1732902 reaction equation
HRID 1732902As productuspto-grants-1980_12
HRID 2148019 reaction equation
HRID 2148019As productTraining data from https://doi.org/10.1039/C8SC04228D (4/10)

Compound notes

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DTXSID0022301
ChEMBL
CHEMBL2289397
UNII
57D0GAO3RX
EC Number
274-322-7
Nikkaji
J73.247H
Refractive Index
Index of refraction: 1.541 at 25 °C/D
Physical DescriptionThick liquid; [Merck Index] Technical product is dark amber liquid; [HSDB] Clear colorless viscous liquid; [MSDSonline]
Stability/Shelf Life · 3 items

Stable to light.

Stable for > 1 year at 37 °C, > 2 years at 25 °C. /Technical flucythrinate/

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 °C; ca 40 at pH 3, 31 at pH 6, 2.6 at pH 9, 29 in distilled water (all at 35 °C).

Collision Cross Section · 2 items

208.3 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID0022301]

200.93 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Physicochemical properties

Melting point
25 ℃ · <25℃
Boiling point
108 ℃ · 108℃ (0.35mmHg)
Density
1.189 g/cm3 · 1.189 g/cm3 (22℃)
vapor pressure
1.2 · 1.2×10-6 Pa (25 °C)
refractive index
1.541 · 1.541 (589.3 nm 25℃)
Flash point
-18 °C · -18 °C
storage temp.
2 · 2-8°C
Water Solubility
0.5 mg · 0.5 mg l-1 (22 °C)
Specific Gravity
1.189 · 1.189 (22℃)
BRN
2195795 · 2195795
Henry's Law Constant
1.1 · 1.1×102 mol/(m3Pa) at 25℃, HSDB (2015)
Major Application
agriculture
InChI
1S/C26H23F2NO4/c1-17(2)24(18-11-13-21(14-12-18)32-26(27)28)25(30)33-23(16-29)19-7-6-10-22(15-19)31-20-8-4-3-5-9-20/h3-15,17,23-24,26H,1-2H3
InChIKey
GBIHOLCMZGAKNG-UHFFFAOYSA-N
SMILES
CC(C)C(C(=O)OC(C#N)c1cccc(Oc2ccccc2)c1)c3ccc(OC(F)F)cc3
CAS DataBase Reference
70124 · 70124-77-5(CAS DataBase Reference)
FDA UNII
57 D0GAO3RX · 57D0GAO3RX
EPA Substance Registry System
Flucythrinate (70124-77-5)
Pesticides Freedom of Information Act (FOIA)
Pay-Off
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
2 · GHS02,GHS06,GHS09
Signal word
Danger
Hazard statements
226 · H226-H301-H332-H410
Precautionary statements
210 · P210-P233-P240-P273-P301+P310-P304+P340+P312
target organs
Respiratory system
Hazard Codes
T,N,Xn,F
Risk Statements
20 · 20/21-25-50/53-67-65-38-11
Safety Statements
36 · 36/37-45-60-61-62
RIDADR
2810 · UN 2810 6.1/PG 3
WGK Germany
3 · 3
RTECS
1578620 · CY1578620
HS Code
29269090 · 29269090
Storage Class
3 · 3 - Flammable liquids
Hazard Classifications
1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Flam. Liq. 2Skin Irrit. 2STOT SE 3
Hazardous Substances Data
70124 · 70124-77-5(Hazardous Substances Data)
Toxicity
50 · LC50 (96-hour) for rainbow trout 0.32 μg/L, bluegill sunsh 0.71 μg/L, channel catsh 0.51 μg/L, sheepshead minnow 1.6 μg/L (Hartley and Kidd, 1987), estuarine mysid 0.008 μg/L, pink shrimp 0.22 μg/L and sheepshead minnow 1.1 μg/L (Schimmel et al., 1983); acute oral LD50 for male and female rats is 81 and 67 mg/kg, respectively (Hartley and Kidd, 1987).
DOT Emergency Guidelines · 5 items

/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.

Other Hazardous Reactions... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/
Hazard Classes and CategoriesFlam. Liq. 3 (71.4%)
Skin, Eye, and Respiratory Irritations · 2 items

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/

Hazardous Reactivities and IncompatibilitiesIncompatibility: Strong oxidizers. /Pyrethrins/

Safety & protection

Fire Fighting Procedures · 4 items

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/

Storage Conditions · 2 items

Do not contaminate water, feed, or food by storage

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/

Cleanup Methods · 3 items

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/

Disposal Methods · 3 items

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/

Preventive Measures · 5 items

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.

Personal Protective Equipment (PPE) · 5 items

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.

Toxicology

Treatment · 1 item

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. (T36)

Interactions · 3 items

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.

Health Effects · 1 item

At high doses, signs of poisoning attributable to flucythrinate 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. (L863)

Ecotoxicity Values · 5 items

LD50 /Anas platyrhynchos/ (Mallard duck) oral >2510 mg/kg

LD50 /Colinus virginianus/ (Bobwhite quail) oral 2708 mg/kg

LC50 /Anas platyrhynchos/ (Mallard duck) dietary 4885 mg/kg diet/8 day

LC50 /Colinus virginianus/ (Bobwhite quail) dietary 3443 mg/kg diet/8 day

For more Ecotoxicity Values (Complete) data for FLUCYTHRINATE (20 total), please visit the HSDB record page.

Environmental Fate · 3 items

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).

Food Survey Values · 1 item

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesInhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
Toxicity Summary · 1 item

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. (T18, L857)

Ecotoxicity Excerpts · 1 item

/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.

Signs and Symptoms · 1 item

Following dermal exposure to flucythrinate, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of flucythrinate. Paralysis can occur after exposure. (L857)

Medical Surveillance · 1 item

Initial medical screening: Employees should be screened for history of certain medical conditions ... which might place the employee at increased risk from /pyrethroid/ exposure. Chronic respiratory disease: In persons with chronic respiratory disease, especially asthma, the inhalation of /pyrethroids/ might cause exacerbation of symptoms due to its sensitizing properities. Skin disease: /Pyrethroids/ can cause dermatitis which may be allergic in nature. Persons with pre-existing skin disorders may be more susceptible to the effects of this agent. Any employee developing the above-listed conditions should be referred for further medical examination. /Pyrethrum/

Regulatory information

FIFRA Requirements · 1 item

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA, as amended in 1988, were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Flucythrinate is found on List B. Case No: 2290; Pesticide type: Insecticide; Case Status: No products containing the pesticide are actively registered ... The case /is characterized/ as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): (+-)-flucythrinate; AI Status: The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Safety data

wgk
3
rtecs
CY1578620
ridadr
UN 2810 6.1/PG 3
hs_code
29269090
Toxicity
LC50 (96-hour) for rainbow trout 0.32 μg/L, bluegill sunsh 0.71 μg/L, channel catsh 0.51 μg/L, sheepshead minnow 1.6 μg/L (Hartley and Kidd, 1987), estuarine mysid 0.008 μg/L, pink shrimp 0.22 μg/L and sheepshead minnow 1.1 μg/L (Schimmel et al., 1983); acute oral LD50 for male and female rats is 81 and 67 mg/kg, respectively (Hartley and Kidd, 1987).
risk_code
20/21-25-50/53-67-65-38-11
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS09
hazard_code
T,N,Xn,F
safety_code
36/37-45-60-61-62
Storage Class
3 - Flammable liquids
target organs
Respiratory system
Hazard statements
H226-H301-H332-H410
Hazard Classifications
Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Flam. Liq. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P210-P233-P240-P273-P301+P310-P304+P340+P312
Hazardous Substances Data
70124-77-5(Hazardous Substances Data)

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/

Principal metabolic pathways involved ester cleavage and oxidation at the para position of the alcohol moiety and at the gem-dimethyl groups of the acid moiety. The metabolite with the hydroxyl substitutent in the alcohol moiety was excreted as the sulphate conjugate in urine. A glycine conjugate was also formed. Alcohol radiolabelled flucythrinate yielded at least 29 urinary metabolites, the principal one being 3-(phenoxy)-hippuric acid. With the acid radiolabel the major urinary metabolite was 2-[4-(difluoromethoxy) phenyl]-3-methylbutyric acid, accounting for 60% of urinary radio activity. (L884)

Absorption, Distribution and Excretion · 4 items

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/

Uses & manufacturing

Uses · 6 items

Used as insecticide, acaricide, and food additive; [HSDB]

Cancelled--no longer registered as a pesticide for use in the US; [HSDB]

Farming (Pesticides) [Category: Industry]

For flucythrinate (USEPA/OPP Pesticide Code: 118301) there are 0 labels match. /SRP: Not registered for current 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./

The active ingredient is no longer contained in any registered pesticide products ... "cancelled."

Pyrethroid ester acaricide and insecticide /SRP: Former in USA/

Consumption Patterns(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
Formulations/PreparationsEmulsifiable concentrate, wettable powder.
General Manufacturing Information · 4 items

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/

Applications · 4 items

DescriptionFlucythrinate is a pyrethroid insecticide once used to control a wide range of pests on various fruit and vegetables but now largely obsolete. It has a low aqueous solubility and a low volatility. It is moderately persistent in soils but less so in water. Based on its physico-chemical properties it is not expected to leach to groundwater. Toxicity data for biodiversity is sparse but high for mammals, bees, fish and aquatic invertebrates. Flucythrinate is high toxic to humans via the oral route and it is considered to be a neurotoxicant.

UsesNonsystemic insecticide.

UsesFlucythrinate controls a wide range of insects on cotton, fruit trees, vines, citrus, bananas, pineapples, olives, coffee, cocoa, hops, vegetables, soyabeans, cereals, alfalfa, sugar beet, sunflowers and tobacco.

General DescriptionFlucythrinate belongs to the class of synthetic pyrethroids, primarily used to control Heliothis spp. in cotton and other insect pests in agricultural crops.

Upstream & downstream products

Upstream raw materials

Concentrated hydrochloric acid2-PhenylethylaMineHexanePyrethrins1,4-DioxaneFenvaleratep-AnisaldehydeDichloromethaneIsovaleric acidDimethyl ether3-Phenoxybenzaldehyde cyanohydrin, 70 wt% solution in ether