Fenpropathrin

HCID 47326CAS 39515-41-8

Basic information

Standard SMILES
CC1(C)C(C(=O)OC(C#N)c2cccc(Oc3ccccc3)c2)C1(C)C
InChIKey
XQUXKZZNEFRCAW-UHFFFAOYSA-N
Molecular formula
C22H23NO3
Average molar mass
349.4 g/mol
Monoisotopic mass
349.1677936

Overview

Yellowish to brown liquid or solid, depending on purity and temperature. Used as an acaricide and insecticide.

Names & identifiers

Preferred name
Fenpropathrin
IUPAC
[cyano-(3-phenoxyphenyl)methyl] 2,2,3,3-tetramethylcyclopropane-1-carboxylate
English name
Fenpropathrin
Molecular formula
C22H23NO3
Molecular weight
349.42

Names & synonyms

Fenpropathrin39515-41-8MeothrinRodyDanimenDanitolFENPROPANATEKilumalMeiothrinMiothrinHeraldSmash
Show more names
DIGITAL2,2,3,3-tetramethyl-cyclopropanecarboxylicacicyano(3-phenoxyphenyl)methyls3206AMITOLXE-938
Danitol FioriOrtho Danitol(+-)-FenpropathrinS 32062,2,3,3-Tetramethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl esterFenpropathrineDTXSID0024002Cyano(3-phenoxyphenyl)methyl 2,2,3,3-tetramethylcyclopropanecarboxylate

Database identifiers

CAS
39515-41-8、64257-84-7
PubChem CID
47326
DTXSID
DTXSID0024002
ChEMBL
CHEMBL522994
ChEBI
CHEBI:39353
UNII
87BH96P0MX
EC Number
254-485-0
Nikkaji
J15.832A

Properties

Computed structural properties

XLogP
5.7
Topological polar surface area
59.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
6
Heavy atoms
26

Experimental & physicochemical properties

Pesticides · 5 items

Pesticide -> EPA IRIS

Acaricides, Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Pyrethrins/Pyrethroids

Pesticide (Fenpropathrin) -> USDA PDB

LogP · 2 items

log Kow = 6.0 @ 20 °C

5.5

Density1.15 @ 25 °C
Color/Form · 2 items

Pale yellow oil

Yellow brown liquid or solid

Solubility · 3 items

In xylene 1000, cyclohexanone 1000, methanol 337 (all in g/kg at 25 °C)

Soluble in common organic solvents (chloroform, acetone, methanol).

In water, 1.41X10-2 mg/l @ 25 °C.

Melting Point45-50 °C

Physicochemical properties

Melting point
47 °C · 47 °C
Boiling point
483.6 °C · 483.6°C (rough estimate)
Density
1.17 · 1.1700 (rough estimate)
refractive index
26 · nD26 1.5283
Flash point
100 °C · 100 °C
storage temp.
-20 °C · -20°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P320, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P260, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P317, P320, P321, P330, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 6 items

Hazard Traits - Environmental tox; Neurotoxicity

Hazard Traits - Developmental Toxicity; Endocrine Toxicity; Neurotoxicity; Reproductive Toxicity

Fenpropathrin is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2002/2076

Cyclopropanecarboxylic acid, 2,2,3,3-tetramethyl-, cyano(3-phenoxyphenyl)methyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

DOT LabelPoison
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Hazards SummaryIn high-dose animal studies, causes tremor, ataxia, rigidity, and liver changes; [RTECS] May cause irritation; [MSDSonline] See Pyrethrum.
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Safety & protection

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Fire Fighting Procedures · 2 items

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/

Storage ConditionsPyrethrins 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 · 1 item

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 /SRP: with HEPA filter/, or by dissolving them in water, or other solvent in the factory environment. /Pesticides/

Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

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

/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/

Target OrgansNervous
Health Effects · 1 item

At high doses, signs of poisoning attributable to fenpropathrin 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 · 3 items

LD50 Mallard ducks oral 1089 mg/kg

LC50 Bobwhite quail dietary >10,000 mg/kg diet/8 day

LC50 Bluegill sunfish 1.95 ug/l/48 hr /Conditions of bioassay not specified/

Environmental Fate · 5 items

AQUATIC FATE: Degraded principally by photolysis with a half-life of 2.7 weeks in river water.

TERRESTRIAL FATE: Duration of activity in soil is ca 1-5 days.

TERRESTRIAL FATE: Based on a classification scheme(1), a range of Koc values from 5,000 to 3.4X10+5(2), indicates that fenpropathrin is expected to be immobile in soil(SRC). Volatilization of fenpropathrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.8X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 5.48X10-6 mm Hg(3), and water solubility, 1.41X10-2 mg/l(3). However, adsorption to soil is expected to attenuate volatilization from moist soil surfaces(SRC). Fenpropathrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Degradation of fenpropathrin is mainly mediated by aerobic microorganisms in soil(4) and photolysis(5). The half-life for disappearance of fenpropathrin in soils was 11 to 17 days under aerobic conditions(4). The time required for half of fenpropathrin to disappear was approximately 4 weeks in soils at a moisture content of 16%, and more than 16 weeks in soils at 4%(4). Fenpropathrin degrades very slowly under anaerobic conditions(4). Eight weeks after its application to both a Kodaira and Azuchi soil (Japan), about 2% of the applied 14C-labeled fenpropathrin evolved as 14C-CO2(4), which corresponds to a half-life of >1 yr(SRC). The half-life of fenpropathrin on the surface of a sterilized sandy loam was 3 to 4 days following irradiation with natural sunlight, and after 15 days it was observed that only about 12% of the original amount remained(5).

AQUATIC FATE: Based on a classification scheme(1), a range of Koc values from 5,000 to 3.4X10+5(2), indicates that fenpropathrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.8X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 5.48X10-6 mm Hg(4), and water solubility, 1.41X10-2 mg/l(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 8 and 98 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 26 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 190(SRC), from its log Kow(4) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Photolysis from sunlit surfaces waters is expected to be an important aquatic fate process for fenpropathrin(SRC). The photolysis half-lives of fenpropathrin in distilled water, distilled water with humic acid, river water, and seawater were 13.5, 6, 2.7, and 1.6 weeks, respectively when exposed to sunlight(8). Hydrolysis may also be an important fate process under alkaline conditions or in warm waters(SRC). At 25 °C, the hydrolysis half-lives of fenpropathrin were approximately 2.2 years and 8 days at pH 7 and 9, respectively, while at 40 °C, the half-lives were about 80 days and 19 hours at pH 7 and 9, respectively (9). No data regarding the biodegradation of fenpropathrin in water were located, however biodegradation studies in soil suggest that fenpropathrin will undergo biodegradation readily(10,11).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fenpropathrin, which has a vapor pressure of 5.48X10-6 mm Hg at 20 °C (2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase fenpropathrin is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 22 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C (SRC) determined using a structure estimation method(3). Particulate-phase fenpropathrin may be removed from the air by wet and dry deposition(SRC). Fenpropathrin also undergoes direct photolysis in the atmosphere(4). Fenpropathrin applied to silica gel plates and irradiated at 360 nm was photodecomposed 72% after 18 hours(4).

Regulatory information

FIFRA Requirements · 2 items

Tolerances are established for residues of the pesticide chemical fenpropathrin )(alpha-cyano-3-phenoxy-benzyl 2,2,3,3-tetramethylcyclopropanecarboxylate) in or on the following agricultural commodities: brassica, head and stem, crop subgroup 5-A; cattle, fat; cattle, mbyp; cattle, meat; citrus, dried pulp; citrus, oil; cottonseed; cottonseed, oil; eggs; fruits, cirtrus, crop group 10; fruits, pome, crop group 11; goats, fat; goats, mbyp; goats, meat; grapes; hogs, fat; hogs, mbyp; hogs, meat; horses, fat; horses, mbyp; horses, meat; milkfat (reflecting 0.08 ppm in whole milk); peanut, hay; peanut, nutmeat; poultry, fat; poultry, mbyp; poultry, meat; raisins; sheep, fat; sheep, mbyp; sheep, meat; squash/cucumber subgroup; strawberry; tomato; and vegetable, cucurbit, melon, crop subgroup 9-A.

Time-limited tolerances are established for residues of the herbicide fenpropathrin in connection with use of the pesticide under section 18 emergency exemptions granted by EPA. The tolerance will expire and is revoked on the date specified: currants (6/30/00); soybeans, forage (6/30/00); soybeans, hay (6/30/00); soybean, hulls (6/30/00); soybeans, meal, (6/30/00); soybean, oil, refined (6/30/00); and soybean, seed (6/30/00).

Safety data

PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
wgk
WGK 3
rtecs
GZ2090000
ridadr
UN 2811 6.1/PG 2
hs_code
29269090
Toxicity
LC50 (24 hr) in rainbow trout: 76.7 ppb (Coats); LD50 in rats (mg/kg): 2.5 i.v. (Verschoyle); in male, female rats (mg/kg): 24-36, 18-24 orally (Crawford)

Chemistry & industry

Pharmacology

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 CNS 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 partial protection against poisoning, it is unlikely that one of these effects represents the primary mechanism of action of the pyrethroids, & most neurotransmitter release is secondary to increased sodium entry. /Pyrethroids/

The symptoms of pyrethrin poisoning follow the typical pattern ... : (1) excitation, (2) convulsions, (3) paralysis, and (4) death. The effects of pyrethrins on the insect nervous system closely resemble those of DDT, but are apparently much less persistent. Regular, rhythmic, and spontaneous nerve discharges have been observed in insect and crustacean nerve-muscle preparations poisoned with pyrethrins. The primary target of pyrethrins seems to be the ganglia of the insect central nervous system although some pyrethrin-poisoning effect can be observed in isolated legs. /Pyrethrins/

Electrophysiologically, pyrethrins cause repetitive discharges and conduction block. /Pyrethrins/

For more Mechanism of Action (Complete) data for FENPROPATHRIN (12 total), please visit the HSDB record page.

Metabolism/Metabolites · 6 items

Metabolism of fenproponate in rats involves rapid oxidase catalyzed ester cleavage followed by hydroxylation.

The metabolic pathways for the breakdown of the pyrethroids vary little between mammalian species but vary somewhat with structure. ... Essentially, pyrethrum & allethrin are broken down mainly by oxidation of the isobutenyl side chain of the acid moiety & of the unsaturated side chain of the alcohol moiety with ester hydrolysis playing & important part, whereas for the other pyrethroids ester hydrolysis predominates. /Pyrethrum and pyrethroids/

The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid & 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 iv route, moderate by slower oral absorption, & often unmeasureably low by dermal absorption. /Pyrethroids/

FASTEST BREAKDOWN IS SEEN WITH PRIMARY ALCOHOL ESTERS OF TRANS-SUBSTITUTED ACIDS SINCE THEY UNDERGO RAPID HYDROLYTIC & OXIDATIVE ATTACK. FOR ALL SECONDARY ALCOHOL ESTERS & FOR PRIMARY ALCOHOL CIS-SUBSTITUTED CYCLOPROPANECARBOXYLATES, OXIDATIVE ATTACK IS PREDOMINANT. /PYRETHROIDS/

For more Metabolism/Metabolites (Complete) data for FENPROPATHRIN (7 total), please visit the HSDB record page.

Fenpropathrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety was subsequently excreted via the urine as the glucuronide conjugate. (L857)

Absorption, Distribution and Excretion · 4 items

/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/

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 and acaricide for fruits, vines, vegetables, ornamentals, cotton, field crops, and greenhouses; [HSDB]

Banned in the EU for use as pesticide for plant protection and other pesticides including biocides; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

For fenpropathrin (USEPA/OPP Pesticide Code: 127901) 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./

Insecticide, acaracide

Control of many species of mites (except rust mites) and insects (eg whiteflies, lepidopterous larvae, leaf miners, leafworms, bollworms) on pome fruit, citrus fruit, vines, vegetables, ornamentals (including ornamental trees) cotton, field crops, and glasshouse crops

Consumption PatternsIn 1992, the estimated agricultural use of fenpropathrin in the United States was about 67 metric tons.
Methods of Manufacturing2,3-Dimethyl-2-butene + ethyl diazoacetate + 3-phenoxybenzaldehyde cyanohydrin (addition/esterification)
Formulations/Preparations · 3 items

Emulsifiable concentrate

Wettable powder, suspension concentrate, ultra-low volume liquid

Mixtures: (fenpropathrin +) clofentezine; fentriothion

General Manufacturing Information · 2 items

Synthetic pyrethroid insecticide with repellant and contact activity ... commercial product is mixture of stereoisomers, the (S)-isomer primarily responsible for the bioactivity.

/Pyrethroids/ are modern synthetic insecticides similar chemically to natural pyrethrins, but modified to increase stability in the natural environment. /Pyrethroids/

Applications · 3 items

DescriptionFenpropathrin is a pyrethroid, non-systemic acaricide and insecticide used to control many species of mite and other insects. It has a low aqueous solubility and is considered to be moderately volatile. It may be persistent in both soil systems and water bodies depending upon local conditions. Based on its physico-chemical properties there is a low risk of leaching to groundwater. Fenpropathrin is highly toxic to bees, fish and aquatic invertebrates and moderately toxic to bird, earthworms and algae. It is also moderately toxic to humans via the oral route. In information on chronic health effects have been identified.

UsesInsecticide, acaricide.

General DescriptionYellowish to brown liquid or solid, depending on purity and temperature. Used as an acaricide and insecticide.

Additional notes

DefinitionChEBI: A cyclopropanecarboxylate ester obtained by formal condensation between 2,2,3,3-tetramethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol.

Related reactions

4 records

Linked notes

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