Fenpropathrin
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Fenpropathrin
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CAS No:
39515-41-8
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Formula:
C22H23NO3
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Chemical Name:
Fenpropathrin
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Synonyms:
Cyclopropanecarboxylic acid,2,2,3,3-tetramethyl-,cyano(3-phenoxyphenyl)methyl ester;SD 41706;WL 41706;S 3206;Fenpropanate;α-Cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate;Fenpropathrin;Meothrin;Meiothrin;Danitol;Miothrin;Danitol Fiori;Kilumal;Smash;Rody;XE 938;Tame;Danitol 10EC;(±)-Fenpropathrin;Danimen;2,2,3,3-Tetramethylcyclopropanecarboxylic acid cyano(3-phenoxyphenyl)methyl ester;Danitol 2.4EC;Lodi Emulsion;64257-84-7
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CAS No:
Description
ChEBI: A cyclopropanecarboxylate ester obtained by formal condensation between 2,2,3,3-tetramethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol.
Yellowish to brown liquid or solid, depending on purity and temperature. Used as an acaricide and insecticide.
Yellowish to brown liquid or solid, depending on purity and temperature. Used as an acaricide and insecticide.|Fenpropathrin is a cyclopropanecarboxylate ester obtained by formal condensation between 2,2,3,3-tetramethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. It has a role as a pyrethroid ester insecticide, a pyrethroid ester acaricide and an agrochemical. It is an aromatic ether and a cyclopropanecarboxylate ester. It derives from a 2,2,3,3-tetramethylcyclopropanecarboxylic acid.
Fenpropathrin Basic Attributes
349.42
349.42
254-485-0
2811|2902
DTXSID0024002
Pale yellow oil|Yellow brown liquid or solid
2926909010
Characteristics
59.3
6.0 @ 20 deg C
1.15 @ 25 deg C
47 °C
448.2±35.0 °C at 760 mmHg
100 °C
1.552
In water, 1.41X10-2 mg/l @ 25 deg C.
Pyrethrins with piperonyl butoxide topical preparations should be stored in well-closed containers at a temperature less than 40 deg C, preferably between 15-30 deg C. /Pyrethrins/
5.48X10-6 mm Hg @ 20 deg C
Oral-rat LD50: 18 mg/kg; Oral-Mouse LD50: 58 mg/kg
Open flame is flammable; heated to decompose toxic nitrogen oxide gas
Yellow-brown solid /Technical fenpropathrin/|Stable except in alkaline solution.
In water, solubility is 14 ppm. Slowly oxidized in air. Decomposed by alkaline solutions.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
A pyrethroid. This compound is an ester and nitrile. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.
Safety Information
UN28116.1/PG2
21-25-26-50/53
28-36/37-38-45-60-61
GZ2090000
T+,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
Pyrethrins /are/ stable for long periods in water-based aerosols where emulsifiers give neutral water systems. /Pyrethrins/
P260-P273-P280-P284-P301 + P310-P310
H301-H312-H330-H410
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.|Incineration would be an effective disposal procedure where permitted. ... /Pyrethrin products/
Incompatible with alkaline materials.|Incompatibility: Strong oxidizers. /Pyrethrins/|... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/
Miyamoto J; Environ Health Perspect 14: 15-28 (1976). Degradation, metabolism, and toxicity of synthetic pyrethroids.|Miyamoto J, et al; Pure Appl Chem 53: 1967-2022 (1981). The chemistry, metabolism, and residue analysis of synthetic pyrethroids.|Hutson DH; Progress in Drug Metabolism 3: 215-252 (1979). The metabolic fate of synthetic pyrethroid insecticides in mammals.|Gammon DW; Fundam Appl Toxicol (5) 1: 9-23 (1985). Correlations between in vitro and in vivo mechanisms of pyrethroid insecticide action.|For more Special Reports (Complete) data for FENPROPATHRIN (6 total), please visit the HSDB record page.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P271, P273, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P320, P321, P322, P330, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 66 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P281, P301+P310, P305+P351+P338, P308+P313, P309+P311, P314, P321, P330, P337+P313, P405, and P501
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: 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. (ERG, 2016)|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/|For more Personal Protective Equipment (PPE) (Complete) data for FENPROPATHRIN (10 total), please visit the HSDB record page.
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/
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/
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/|For more Preventive Measures (Complete) data for FENPROPATHRIN (10 total), please visit the HSDB record page.
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.
SOURCE DOMINATED: The maximum airborne residues of fenpropathrin in greenhouse air after application was 0.29 ug/cu cm(1). However, airborne residues in over 75% of the samples were below the limit of quantization (i.e., 0.1 ug/cu cm)(1).|RURAL/REMOTE: Mean and max concn of fenpropathrin in air (gas phase) collected at Colmar (eastern France) between 1991 and 1993 was 0.5 and 2.7 ng/ml, respectively(1); the mean and max concn of fenpropathrin in air (particulate phase) was 0.6 and 4 ng/ml, respectively(1).
Toxicity
highly toxic
/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/
LD50 Rat male oral 70.6 mg/kg (in corn oil)|LD50 Rat female oral 66.7 mg/kg (in corn oil)|LD50 Rat male percutaneous 1000 mg/kg|LD50 Rat female percutaneous 870 mg/kg|LD50 Rabbit percutaneous >2000 mg/kg
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. ... /Pyrethroids/
Fenpropathrin's production and use as an insecticide(1) is expected to result in its direct release to the environment(SRC).
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).
The rate constant for the vapor-phase reaction of fenpropathrin with photochemically-produced hydroxyl radicals has been estimated as 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 22 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Fenpropathrin adsorbs light in the environmental UV spectrum and undergoes photolysis in the environment. Fenpropathrin applied to silica gel plates and irradiated at 360 nm was photodecomposed 72% after 18 hours(2). 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(3). The hydrolysis of fenpropathrin in buffer solution was studied under various pH and temperature conditions(4). At 25 °C, the hydrolysis half-lives of fenpropathrin were approximately 2.2 years and 8 days at pH 7 and 9, respectively(4). At 40 °C, the half-lives were about 80 days and 19 hours at pH 7 and 9, respectively(4).
An estimated BCF of 190 was calculated for fenpropathrin(SRC), using a log Kow of 6(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC). However, bioconcentration studies on compounds which are structurally similar suggest that bioconcentration may be lower than that indicated by the regression-derived equations due to the ability of aquatic organisms to readily metabolize this class of compounds(4).
Koc values for fenpropathrin range from 5,000 to 340,000(1). According to a classification scheme(2), these Koc values suggest that fenpropathrin is expected to be immobile in soil(SRC).
The Henry's Law constant for fenpropathrin is estimated as 1.8X10-4 atm-cu m/mole(SRC) based upon its vapor pressure, 5.48X10-6 mm Hg(1), and water solubility, 1.41X10-2 mg/l(1). This Henry's Law constant indicates that fenpropathrin is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 8 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 98 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The estimated volatilization half-life from a model pond is 26 years if adsorption is considered(3). Fenpropathrin's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization from moist soil surfaces may be attenuated by adsorption to soil(SRC). Fenpropathrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
RAIN/FOG: Mean and max concn of dissolved fenpropathrin in rainwater collected at Colmar (eastern France) between 1991 and 1993 was 0.26 and 5 ng/ml, respectively(1); the mean and max concn of dissolved fenpropathrin in fogwater was 2.5 and 17 ng/ml, respectively(1); the mean and max concn of particle bound fenpropathrin in fogwater was 70 and 900 ng/ml, respectively(1).
Occupational exposure to fenpropathrin may occur through inhalation and dermal contact with this compound at workplaces where fenpropathrin is produced or used. Monitoring data indicate that the general population may be exposed to fenpropathrin via inhalation of ambient air containing fenpropathrin. (SRC)
Drug Information
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/
/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/
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.
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.
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)
Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
Treatment is supportive, and most casual exposures require only decontamination. Topical vitamin E may ameliorate the paresthesias that accompany contact with synthetic pyrethroids containing an alpha-cyano group (e.g., fenvalerate, cypermethrin, flucythrinate). /Synthetic pyrethroids/|The additives (e.g. petroleum distillate), when present, represent a greater toxic threat to the patient than the active ingredient itself. ... Emesis should not be induced when petroleum distillate additives are present. The alert person with an intact gag reflex & a sublethal pyrethrum ingestion without other toxic constituents may have emesis induced by ipecac, followed by a saline cathartic & slurry of activated charcoal. ... Pulmonary & allergic sequelae are treated symptomatically with airway maintenance, oxygen, & ventilatory assistance as required. Standard drugs and management protocols may be used for treatment of bronchospasm & anaphylaxis. Seizures are treated with diazepam. /Pyrethrum and synthetic pyrethroids/|Skin decontamination. Wash skin promptly with soap and water ... . If irritant or paresthetic effects occur, obtain treatment by a physician. Because volatilization of pyrethroids apparently accounts for paresthesia affecting the face, strenuous measures should be taken (ventilation, protective face mask and hood) to avoid vapor contact with the face and eyes. Vitamin E oil preparations (dL-alpha tocopheryl acetate) are uniquely effective in preventing and stopping the paresthetic reaction. They are safe for application to the skin under field conditions. Corn oil is somewhat effective, but possible side effects with continuing use make it less suitable. Vaseline is less effective than corn oil. Zinc oxide actually worsens the reaction. /Pyrethroids/|Eye contamination. Some pyrethroid compounds can be very corrosive to the eyes. Extraordinary measures should be taken to avoid eye contamination. the eye should be treated immediately by prolonged flushing of the eye with copious amounts of clean water or saline. If irritation persists, obtain professional ophthalmologic care. /Pyrethroids/|Other treatments. Several drugs are effective in relieving the pyrethroid neurotoxic manifestations observed in deliberately poisoned laboratory animals, but none has been tested in human poisonings. Therefore, neither efficacy nor safety under these circumstances is known. Furthermore, moderate neurotoxic symptoms and signs are likely to resolve spontaneously if they do occur. /Pyrethroids/
In a study of transient abnormal facial sensation produced by the pyrethroids, fenproponate was the compound most frequently associated with symptoms. This was after direct application of concentrates to the facial skin or after exposure to dusts. Symptoms involved a tingling sensation, not associated with loss of normal sensation, distributed over the face, especially under the eyes & around the nose. These symptoms appeared within 0.5-3 hr, persisted for 0.5-8 hr, were not associated with any abnormal neurological or electrophysiological changes, & would appear to represent a milder form of the paresthesia reported for other pyrethroids.|Synthetic pyrethroids are neither cutaneous sensitizers nor irritants. Although these compounds do not cause signs of inflammation (edema, erythema, vesiculation), they do produce paresthesias after contact. Typically, symptoms begin several hours after cutaneous exposure, peak in the evening, and resolve by the following day. /Synthetic pyrethroids/|Contact allergy from pyrethroids ... has not been observed. /Pyrethroids/|The allergenic properties of pyrethroids /with early pyrethrum preparations/ are marked in comparison with other pesticides. Many cases of contact dermatitis and respiratory allergy have been reported. Persons sensitive to ragweed pollen are particularly prone to such reactions. Preparations containing synthetic pyrethroids are less likely to cause allergic reactions than are the preparations made from pyrethrum powder. /Pyrethroids/|For more Human Toxicity Excerpts (Complete) data for FENPROPATHRIN (6 total), please visit the HSDB record page.
fenpropathrin
Fenpropathrin Use and Manufacturing
2,3-Dimethyl-2-butene + ethyl diazoacetate + 3-phenoxybenzaldehyde cyanohydrin (addition/esterification)
Insecticide, acaricide.
In 1992, the estimated agricultural use of fenpropathrin in the United States was about 67 metric tons.
Emulsifiable concentrate|Wettable powder, suspension concentrate, ultra-low volume liquid|Mixtures: (fenpropathrin +) clofentezine; fentriothion
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/
Product analysis is by high performance liquid chromatography or by gas liquid chromatography with flame ionization detector. Residue may be determined by gas liquid chromatography with electron capture detector.|Pyrethrins ... in pesticide formulations are analyzed using gas chromatography equipped with flame ionization detection. Average recovery is 98% with a precision of 0.0044-0.011. /Pyrethrins/|... Liquid chromatography method has been developed to quantitate pyrethrins in pesticide formulations. ... Detection was monitored at 240 nm. ... Percent coefficients of variation ranged from 1.39 to 9.68 with the majority less than 5.00. ... /Pyrethrins/|Pyrethrins were detected in soils by gas chromatography after extraction with hexane. /Pyrethrins/|Low level pyrethrin formulations are extracted with tetrahydrofuran and determined via capillary gas chromatography with electron capture detection. ... Analysis of 5 formulations gave an average standard deviation of 3.3%. /Pyrethrins/
Agrochemicals -> Acaricides, Insecticides
Computed Properties
Molecular Weight:349.4
XLogP3:5.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:349.16779360
Monoisotopic Mass:349.16779360
Topological Polar Surface Area:59.3
Heavy Atom Count:26
Complexity:553
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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