Phenothrin
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Phenothrin
structure -
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CAS No:
26002-80-2
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Formula:
C23H26O3
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Chemical Name:
Phenothrin
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Synonyms:
Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-,(3-phenoxyphenyl)methyl ester;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methylpropenyl)-,m-phenoxybenzyl ester;Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methyl-1-propenyl)-,(3-phenoxyphenyl)methyl ester;Benzyl alcohol,m-phenoxy-,2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate;Phenothrin;S 2539;m-Phenoxybenzyl 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate;Phenoxythrin;OMS 1809;OMS 1810;3-Phenoxybenzyl chrysanthemate;Pibutin;Multicide 2154;PT 515;S 2539 (pesticide);Duet;Anchimanaito 20S;Phenothrin II;53528-32-8;73170-79-3;2048189-09-7
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CAS No:
Description
Phenothrin is a synthetic pyrethroid that kills adult fleas and ticks. It has also been used to kill head lice in humans.
Phenothrin is a pale yellow to yellow-brown liquid. Non corrosive. Used as an insecticide.|PALE YELLOW-TO-YELLOW-BROWN LIQUID.
Phenothrin is a pale yellow to yellow-brown liquid. Non corrosive. Used as an insecticide.|Phenothrin is a cyclopropanecarboxylate ester. It has a role as a pyrethroid ester insecticide. It derives from a chrysanthemic acid.
Phenothrin Basic Attributes
350.45
350.45
247-404-5
707484X33X
0313
758668
3082|2902
DTXSID7032688
Colorless liquid|Pale yellow to yellow-brown clear liquid
P - Antiparasitic products, insecticides and repellents
29162090
Characteristics
35.5
7.54 (est)
YELLOW TO YELLOW BROWN LIQUID.
1.06 g/cm3 @ Temp: 20 °C
<25 °C
>290 °C
186.6±23.3 °C
1.588
Solubility in water: none
0-6°C
Vapour pressure, Pa at 20°C:
LD50 orl-rat: >10 g/kg YKYUA637,1481,86
Faint characteristic odor
Henry's Law constant = 6.8X10-6 atm-cu m/mol at 25 °C (est)
187.5 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]
Hydroxyl radical reaction rate constant = 1.06X10-10 cu cm/molec-sec at 25 °C (est)
Insoluble in water. Hydrolyzed by alkalis.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
A pyrethroid derivative.
Safety Information
UN30829/PG3
3
20/21/22-50/53
13-60-61-24-23
GZ1975000
Xn,N
Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
Stable. Combustible. Incompatible with strong oxidizing agents. Light sensitive.
P273-P280-P501
H302-H312-H332-H410
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.|This pesticide is highly toxic to fish and aquatic invertebrates. Do not discharge effluent containing this product into lakes, streams, ponds, estuaries, oceans, or other waters unless in accordance with the requirements of a National Pollutant Discharge Eliminations System (NPDES) permit and the permitting authority has notified in writing prior to discharge.|Incineration would be an effective disposal procedure where permitted. ... /Pyrethrin products/|Disposal: Waste that contains d-phenothrin should be burnt in an appropriate high-temperature incinerator with effluent scrubbing. If no incinerator is available, contaminated absorbents or surplus products should be decomposed by hydrolysis at pH 12 or above. Contact with a suitable hydrolyzing agent is required to ensure degradation of the active ingredient to a safe level. For emulsifiable material, use 5% sodium hydroxide (caustic soda) solution or saturated (7-10%) sodium carbonate (washing soda) solution. For non-emulsifiable material, use a 1:1 mixture (by volume) of caustic soda or washing soda (as above) and a water/oil soluble solvent such as denatured alcohol, monoethylene glycol, hexylene glycol, or isopropylalcohol. Cover the material with a hydrolyzing agent and let it stand for 7 days. Before disposal, the waste must be analyzed to ensure that the active ingredient has been degraded to a safe level. Never pour untreated waste or surplus products into public sewers or where there is any danger of run-off or seepage to streams, water-courses, open waterways, ditches, fields with drainage systems, or to the catchment areas of boreholes, wells, springs, or ponds.
Incompatible with alkaline materials.|... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - d-Phenothrin. (September 2008). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of May 26, 2009: http://www.epa.gov/pesticides/reregistration/status.htm]|USEPA, Office of Prevention, Pesticides, and Toxic Substances; Revised HED Human Health Risk Assessment for d-Phenothrin (26002-80-2) (February 6, 2008). EPA Docket No.: EPA-HQ-OPP-2008-0140-0002.|California Environmental Protection Agency/Department of Pesticide Regulation; Toxicology Data Review Summaries on Phenothrin (726002-80-2).[Available from, as of May 7, 2009: http://www.cdpr.ca.gov/docs/risk/toxsums/toxsumlist.htm]|WHO/FAO Data Sheet on Pesticides No. 85: d-Phenothrin (1994).[Available from, as of May 28, 2009: http://www.inchem.org/documents/pds/pds/pest85_e.htm]|International Program on Chemical Safety; Health and Safety Guide No. 32: d-Phenothrin (1989).[Available from, as of May 28, 2009: http://www.inchem.org/documents/hsg/hsg/hsg032.htm]
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)|Combustible. Liquid formulations containing organic solvents may be flammable.
|Warning|H302 (96.63%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P391, and P501|Aggregated GHS information provided by 186 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 46 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. (ERG, 2016)|Applicators and other handlers must wear long-sleeve shirts and long pants, ... shoes plus socks, /and/ PF5 Respirator when mixing, loading, and applying Liquid Concentrates including Emulsifiable Concentrates at the Maximum Use Rate Identified on the Product Label.|PF5 Respirator when mixing, loading, and applying Liquid Concentrates including Emulsifiable Concentrates at the Maximum Use Rate Identified on the Product Label.|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/
Combustible. Liquid formulations containing organic solvents may be flammable.
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/|Some solvents in pyrethroid formulations are highly flammable. DO NOT USE WATER to extinguish fires. Use dry powder, carbon dioxide, or alcohol-resistant foam, sand, or earth. Cool nearby drums with water spray.
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a POTW is acceptable only after review by the governing authority. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must meet Hazardous Material Criteria for disposal.|Spillage Keep spectators away from leaking or spilled product. Prohibit smoking and the use of naked flames in the immediate vicinity. Avoid exposure by wearing appropriate protective clothing and masks. Transfer any product remaining in damaged or leaking containers into a clean, empty drum, and label the drum. Absorb spillage and cover contaminated area with lime, damp sawdust, sand, or earth, and place in a secure container for safe disposal. Contain a large spillage by building a barrier of earth or sandbags. Prevent liquid from spreading to other cargo, vegetation, or waterways by containing it with the most readily available barrier material, e.g., earth or sand. Decontaminate empty, damaged, or leaking containers with a 10% sodium carbonate solution added at the rate of at least 1 L per 20-L drum. Puncture containers to prevent reuse.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|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.|Follow manufacturer's instructions for cleaning /and/ maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry.|For more Preventive Measures (Complete) data for PHENOTHRIN (16 total), please visit the HSDB record page.
The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes.
Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is irritating to the eyes.
NO open flames.
PREVENT GENERATION OF MISTS!
Use ventilation, local exhaust or breathing protection.
Protective gloves.
Wear safety goggles.
Toxicity
/Pyrethroid/ detoxification ... important in flies, may be delayed by the addition of synergists ... organophosphates or carbamates ... to guarantee a lethal effect. ... /Pyrethroid/
LD50 Rat oral greater than 500 mg/kg|LD50 Mouse oral greater than 500 mg/kg|LD50 Rat oral greater than 10000 mg/kg /(1R)-cis,trans-isomeric mixture/|LD50 Mouse oral greater than 10000 mg/kg /(1R)-cis,trans-isomeric mixture/|For more Non-Human Toxicity Values (Complete) data for PHENOTHRIN (18 total), please visit the HSDB record page.
/FIELD STUDIES/ Synthetic pyrethroids have been shown to be toxic for fish, aquatic arthropods, and honeybees in laboratory tests. But, in practical usage, no serious adverse effects have been noticed because of the low rates of application and lack of persistence in the environment. The toxicity of synthetic pyrethroids in birds and domestic animals is low. /Pyrethroids/
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/
Phenothrin's production may result in its release to the environment through various waste streams; its use as an insecticide(1) will result in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a log Kow of 6.01(2) and a regression-derived equation(3), indicates that phenothrin is expected to be immobile in soil(SRC). Volatilization of phenothrin from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant, of 6.8X10-6 atm-cu m/mole(SRC), based upon its vapor pressure, 1.43X10-7 mm Hg(2), and water solubility, 9.7X10-3 mg/L(2). However, adsorption to soil is expected to attenuate volatilization(SRC). Phenothrin is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.43X10-7 mm Hg(2). Although environmental biodegradation data specific to phenothrin were not available, the pyrethroid class of insecticides is readily degraded by environmental microorganisms(4,5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.2X10+5(SRC), determined from a log Kow of 6.01(2) and a regression-derived equation(3), indicates that phenothrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 6.8X10-6 atm-cu m/mole(2), based upon its vapor pressure, 1.43X10-7 mm Hg(2), and water solubility, 9.7X10-3 mg/L(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 days and 81 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 120 years if adsorption is considered(5). According to a classification scheme(6), an estimated BCF of 230(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high, provided the compound is not metabolized by the organism(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), phenothrin, which has a vapor pressure of 1.43X10-7 mm Hg at 21 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase phenothrin 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 4 hours(SRC), calculated from its rate constant of 1.06X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The half-life for the vapor-phase reaction of phenothrin with ozone has been estimated as about 38 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(4). Particulate-phase phenthrin may be removed from the air by wet or dry deposition(SRC). Oxygen species are involved in the photodegradation of phenothrin on glass(5); suggesting that phenothrin may be susceptible to photodegradation by sunlight(SRC).
Both phenothrin isomers (trans and cis) were applied to wheat grain containing 11% moisture at a rate of 4 ppm; levels were monitored while grain was stored in dark at 15 or 30 °C. Both isomers degraded slowly. After 12 mo 79% and 97$ remained in grain stored at 30 °C. Both isomers were metabolized through hydrolysis of ester linkage, the oxidation of benzyl alcohol to benzoic acid, and the methylation of benzoic acid.|The rate constant for the vapor-phase reaction of phenothrin with photochemically-produced hydroxyl radicals has been estimated as 1.06X10-6 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of phenothrin with ozone has been estimated as 4.3X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 38 minutes at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). In addition, reaction with nitrate radicals may also be important(SRC).|Hydrolysis half-lives for (cyclopropyl-1-14C)-d-trans- phenothrin are 301, 495, and 120 days at pH values of 5, 7 and 9, respectively(1); for (benzyl-14C)-d-trans-phenothrin, 301, 578, and 91 days at pH values of 5, 7 and 9, respectively(2). Phenothrin is susceptible to alkaline hydrolysis(3). Oxygen species are involved in the photodegradation of phenothrin on glass(4). Both trans- and cis- isomers of phenothrin rapidly degraded on kidney bean and rice plants via unique ozonization of the isobutenyl side chain successively to the corresponding aldehyde and carboxylic acid(4). Chrysanthemic acid is a major photoproduct in the photolysis of phenothrin(5).
An estimated BCF of 230 was calculated for phenothrin(SRC), using a log Kow of 6.01(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, provide the compound is not metabolized by the organism(SRC).
The Koc of phenothrin is estimated as 1.2X10+5(SRC), using a log Kow of 6.01(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that phenothrin is expected to be immobile in soil.
The Henry's Law constant for phenothrin is estimated as 6.8X10-6 atm-cu m/mole(1), based upon its vapor pressure 1.43X10-7 mm Hg(1), and water solubility, 9.7X10-3 mg/L(1). This Henry's Law constant indicates that phenothrin 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 7 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 81 days(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 120 years if adsorption is considered (3). Phenothrin's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Phenothrin is not expected to volatilize from dry soil surfaces(SRC) based its vapor pressure(1).
Residues of phenothrin were highly persistent on stored wheat. During milling, residues accumulated in bran fractions and were reduced in white flour. They were not significantly /reduced/ during baking.
Occupational exposure to phenothrin may occur through inhalation and dermal contact with this compound at workplaces where phenothrin is produced or used. Use data indicate that the general population may be exposed to phenothrin via inhalation and dermal contact with consumer products containing phenothrin. (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/|One hundred and one subjects with head louse infestation were entered into two separate studies, in which a phenothrin aqueous/alcoholic lotion was compared to a carbaryl lotion and a malathion lotion. Fifty subjects were treated with a single application of the phenothrin lotion, 28 with the carbaryl lotion and 23 with the malathion lotion. In the comparative study of the phenothrin and malathion lotions an inspection on the day following treatment showed no live lice remained, but that six of the subjects treated with malathion lotion still had evidence of viable eggs (p < 0.05). In one subject viable eggs were still evident at two weeks post-treatment. There were no cases, however, of live lice or viable eggs at four weeks post-treatment. Mild cutaneous side-effects were reported in five subjects, the incidence of which was not significantly different by treatment group. One subject in the phenothrin and carbaryl lotion comparative study had evidence of live lice at one week post-treatment with phenothrin lotion. This subject received no further treatment and was clear of both live lice and viable eggs at subsequent visits. A separate case of live lice infestation was found at two weeks post-treatment in a subject treated with phenothrin lotion and at four weeks post-treatment in two subjects treated with carbaryl lotion. As these subjects were free of live lice infestation at previous follow-up visits it was highly probable that these were cases of re-infestation from another source.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)
Dermal adsorption of (+)trans- and (+)cis-phenothrin into body of male rats from dust or emulsifiable concentrate (EC) was estimated to be 3-7% and 8-17%. The rate of absorption was 4-5 times faster with EC than with dust and T/2 in blood was 2-3 times longer.|(14)C-phenothrin labeled at the hydroxymethyl group of the alcohol moiety was orally admin at ... 200 mg/kg to male Sprague-Dawley rats. Absorption and elimination was rapid. About 60% of radioactivity was eliminated in urine and 40% in feces in 3 days. In addn to phenothrin, 3-phenoxybenzyl alcohol and 3-phenoxybenzoic acid were found in brain, liver, kidney, and blood. Unidentified water and ether solubles were also present.|Dermal adsorption of (+)trans- and (+)cis-phenothrin into body of male rats from dust or emulsifiable concentrate (EC) was estimated to be 3-7% and 8-17%. Rate of absorption was 4-5 times faster with EC than with dust. Amount absorbed through skin was almost completely excreted into urine and feces within 6 days. When admin once orally, at rate of 2 mg/kg (either isomer), about 96% of dose was recovered in excreta during following 6 days. A larger amt of (+)cis-isomer was excreted in feces than (+)trans-isomer and a larger amt of (+)trans-isomer was excreted in urine than (+)-cis-isomer.|The tissue residues in rats 7 days after a single oral dose of (14)C-(1R,cis)- or (14)C-(1R,trans)-phenothrin at 10 mg/kg body weight were generally very low although the fat showed somewhat higher residue levels (1-2.5 mg/kg). Similarly, high 14C residue levels (up to 23 mg/kg) were found in the fat, 7 days after a single oral dose of the [1R,cis] isomer at 200 mg/kg body weight.|For more Absorption, Distribution and Excretion (Complete) data for PHENOTHRIN (13 total), please visit the HSDB record page.
(14)C-Phenothrin ... was orally admin at ... 200 mg/kg to male Sprague-Dawley rats. ... Urine contained low levels of 3-phenoxybenzoic acid and its glycine conjugate and some ether and water sol material. In addn ... 3-(4'-hydroxyphenoxy)benzoic acid was present and accounted for 42.3% of radioactivity ... This cmpd was ... major metab in feces but accounted for only 11.9% of ... radioactivity. In addn to unchanged phenothrin and unidentified water and ether solubles, feces contained 3-phenoxybenzoic acid and the glycine conjugate. 3-phenoxybenzyl alcohol was not observed in urine or feces.|Dermal and oral admin of (+)trans- and (+)cis-phenothrin to male rats from dust or emulsifiable concentrate produced nearly the same metabolites. Major metabolites from (+)trans-isomer were 3-phenoxybenzoic acid and its glycine conjugate and (3,4'-hydroxyphenoxy)benzoic acid and its sulfate. The cis-isomer gave larger amounts of ester metabolites.|When [1R,trans]-phenothrin was given to rats at 4, 10, or 200 mg/kg body weight (oral single dose) or 4 mg/kg body weight (repetitive oral dose for 14 days), the sulfate conjugate of 4'-OH-phenoxy benzoic acid was predominant, accounting for 28, 43, 28, and 55%, respectively, of the dose. In addition, phenoxy benzoic acid (4, 10, 5, and 6%), its glycine conjugate (1,3,2, and 2%) and glucuronide (2,3,1, and 3%), and free 4'-OH-phenoxybenzoic acid (2,11,3, and 3%) were found. The sulfate conjugate of 3-(2'-hydroxyphenoxy)benzoic acid (2'-OH-PBacid) was also found as a minor metabolite.|When Sprague Dawley rats were administered a single oral dose of [1R,trans]-phenothrin at 4 or 200 mg/kg body weight level or given an oral dose of 4 mg/kg body weight per day for 14 days, unmetabolized compound was found in the feces (44-45, 44-60, and 14-16% of the dose, respectively). An ester-form metabolite, the 4'-hydroxy phenoxy benzoic acid derivative of trans-phenothrin, was also detected (0.4-0.6%).|For more Metabolism/Metabolites (Complete) data for PHENOTHRIN (14 total), please visit the HSDB record page.
Following absorption through the chitinous exoskeleton of arthropods, pyrethrins stimulate the nervous system, apparently by competitively interfering with cationic conductances in the lipid layer of nerve cells, thereby blocking nerve impulse transmissions. Paralysis and death follow. /Pyrethrins/|Some synthetic pyrethroids given intravenously to rats cause either tremor (T-syndrome) or choreoathetosis with salivation (CS-syndrome). However, d-phenothrin (>600 mg/kg body weight) injected intravenously into the lateral tail vein caused neither T-syndrome nor CS syndrome, due to its very low acute toxicity. From a study involving intracerebral dosing with [1R,cis]- or [1R, trans]-phenothrin in mice, both compounds were classified as Type I pyrethroids based on the occurrence of tremors and on neurophysiological studies in cockroach cercal sensory nerves.|The effects of 4 different pyrethroid insecticides on sodium channel gating in internally perfused, cultured mouse neuroblastoma cells (N1E-115) were studied using the suction pipette, voltage clamp technique. Pyrethroids increased the amplitude of the sodium current, sometimes by more than 200%. Activation of the sodium current occurred at more hyperpolarized potentials than under control conditions. The declining phase of the sodium current during depolarization was markedly slowed down and after repolarization of the membrane a large, slowly decaying sodium tail current developed. Pyrethroids did not affect the sodium current reversal potential, steady-state sodium inactivation or recovery from sodium channel inactivation. The amplitude of the pyrethroid-induced slow tail current was always proportional to the sodium current at the end of the preceding depolarizing pulse. The rate of decay of the slow tail current strongly depended on pyrethroid structure and increased in the order deltamethrin, cyphenothrin, fenfluthrin and phenothrin. The rate of decay further depended on membrane potential and temperature. Below -85 m V the instantaneous current-voltage relationship of the slow tail current showed a negative slope conductance. The tail current decayed more slowly at low temperatures. Arrhenius plots indicated that the relaxation of open sodium channels to a closed state involved a higher energy barrier for pyrethroid-affected than for normal channels. The energy barrier was higher after deltamethrin than after the non-cyano pyrethroid fenfluthrin. It is concluded that in mammalian neuronal membrane pyrethroids selectively reduce the rate of closing of sodium channels both during depolarization and after repolarization of the nerve membrane.|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 (eg, permethrin, bioresmethrin). The former group of pyrethroids causes more cutaneous sensations than the latter. /Synthetic pyrethroids/|For more Mechanism of Action (Complete) data for PHENOTHRIN (11 total), please visit the HSDB record page.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Inhalation of material may be harmful. Contact may cause burns to skin and eyes. Inhalation of Asbestos dust may have a damaging effect on the lungs. Fire may produce irritating, corrosive and/or toxic gases. Some liquids produce vapors that may cause dizziness or suffocation. Runoff from fire control may cause pollution. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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. 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. (ERG, 2016)
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Emergency and supportive measures: Treat bronchospasm and anaphylaxis if they occur. Observe patients with a history of large ingestions for at least 4-6 hours for any signs of CNS depression or seizures. /Pyrethrins and pyrethroids/|Decontamination: Inhalation: Remove victims from exposure and give supplemental oxygen if needed. Skin: Wash with copious soap and water. Topical application of vitamin E in vegetable oil was reported anecdotally to relieve paresthesias. Eyes: Irrigate with copious water. After irrigation, perform a fluorescein examination and refer the victim to an ophthalmologist if there is evidence of corneal injury. Ingestion: In the majority of cases, a subtoxic dose has been ingested and no decontamination in necessary ... Gastric lavage is not necessary after small ot moderate ingestions if activated charcoal can be given promptly. /Pyrethrins and pyrethroids/|Enhanced elimination: These compounds are metabolized rapidly by the body, and extracorporeal methods of elimination would not be expected to enhance their elimination. /Pyrethrins and 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/|For more Antidote and Emergency Treatment (Complete) data for PHENOTHRIN (9 total), please visit the HSDB record page.
/HUMAN EXPOSURE STUDIES/ d-Phenothrin (talc powder formulation with Span 80 as a stabilizer) was applied to the head hair and pudendal hair of eight male human volunteers (three times at intervals of 3 days) at a dose of 32 mg/man per administration (0.44 to 0.67 mg/kg body weight per day). d-Phenothrin powder was washed off 1 hr after application. There were no significant abnormalities due to d-phenothrin in terms of dermal irritation, clinical signs, or blood biochemical and hematological parameters. The blood levels of d-phenothrin were below the detection limit ...|/SIGNS AND SYMPTOMS/ 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/|/SIGNS AND SYMPTOMS/ Some pyrethroid (eg, deltamethrin, fenvalerate, cyhalothrin, lambda-cyhalothrin, flucythrinate, and cypermethrin) may cause a transient itching and/or burning sensation in exposed human skin. /Synthetic pyrethroids/|/SIGNS AND SYMPTOMS/ The clinical manifestations of inhalation exposure to pyrethrins can be local or systemic. Localized reactors confined to the upper respiratory tract include rhinitis, sneezing, scratchy throat, oral mucosal edema, and even laryngeal mucosal edema. Localized reaction of the lower respiratory tract include cough, shortness of breath, wheezing, and chest pain. An asthmalike reaction occurs with acute exposures in sensitized patients. Hypersensitivity pneumonitis characterized by chest pain, cough, dyspnea, & bronchospasm may occur in an individual chronically exposed. /Pyrethrum and synthetic pyrethroids/
(3-phenoxyphenyl)methyl cis,trans-(+)-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Redness.
Phenothrin Use and Manufacturing
3-Phenoxybenzyl alcohol + (1RS)-cis/trans-chrysanthemic acid (esterification)|Preparation of racemic mixture: N. Itaya et al., DE 1926433 corresponding to US 3666789 (1969, 1972 to Sumitomo).
Insecticide.
Phenothrin is available as a ready-to-use (RTU) indoor spray and carpet powder, pressurized concentrate, emulsifiable concentrate, and is formulated for use in pet spot-on and stripe-on flea and tick treatments. Formulations for pet use often contain other active ingredients in addition to phenothrin. Phenothrin is also formulated for use with ultra-low volume (ULV) sprayers and indoor foggers.|Emulsifiable concentrate, aerosol, oil liquid, powder.|USEPA/OPP Pesticide Code 069005; Trade Names: Forte, Phenothrin (26002-80-2), Phenoxythrin, S-2539, Sumithrin, Phenothrin, Fenothrin.|d-Phenothrin is a synthetic pyrethroid insecticide. Racemic phenothrin was invented in 1969. It is a mixture of four stereoisomers. d-Phenothrin is a mixture of the two isomers that have the highest activity and is the only technical product commercially available. The technical grade is 92.5-94.5% pure.|For more Formulations/Preparations (Complete) data for PHENOTHRIN (201 total), please visit the HSDB record page.
The WHO Recommended Classification of Pesticides by Hazard identifies Sumithrin (Phenothrin) as unlikely to present an acute hazard in normal use; Main Use: Insecticide.|Phenothrin is often formulated with piperonyl butoxide (or PBO), as a synergist which increases the effectiveness of phenothrin as an insect knockdown agent.|Phenothrin has strong activity against Hemiptera, Lepidoptera, and Diptera, and was highly effective against insects resistant to chlorinated hydrocarbons, organophosphates, and carbamates.|Phenothrin applied to wheat stored for 52 wk had a half-life of 72 and 29 wk at 25 °C (12% moisture) and 35 °C (15% moisture).|For more General Manufacturing Information (Complete) data for PHENOTHRIN (9 total), please visit the HSDB record page.
Method: EPA 1660; Procedure: high performance liquid chromatography with ultraviolet detection; Analyte: phenothrin; Matrix: municipal and industrial wastewater; Detection Limit: 1 ug/L.|GAS CHROMATOGRAPHIC & HIGH PERFORMANCE LIQUID CHROMATOGRAPHIC METHODS WERE DEVELOPED FOR DETERMINATION OF SYNTHETIC PYRETHOIDS (INCL PHENOTHRIN) IN FORMULATED PRODUCTS.|METHODS OF EXTRACTION & ANALYSIS SUITED FOR ANALYSIS OF AGED, UNKNOWN RESIDUES ON WHEAT, BARLEY, OATS, SORGHUM, RICE IN HUSK, MILLED RICE, POLISHED RICE & COOKED RICE ARE REPORTED FOR PYRETHROIDS (INCL PHENOTHRIN & D-PHENOTHRIN). PYRETHROIDS, AFTER ALKALINE HYDROLYSIS, WERE DETERMINED COLORIMETRICALLY FROM REACTION OF CHRYSANTHEMIC ACID WITH ACIDIFIED MERCURY (II) SULFATE.|GAS CHROMATOGRAPHY USED FOR ANALYSIS OF PYRETHROID RESIDUES (INCL PHENOTHRIN) IN VEGETABLES & FRUITS.
Agrochemicals -> Insecticides
Computed Properties
Molecular Weight:350.4
XLogP3:6.2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:7
Exact Mass:350.18819469
Monoisotopic Mass:350.18819469
Topological Polar Surface Area:35.5
Heavy Atom Count:26
Complexity:512
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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