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Prallethrin

HCID 9839306
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
23031-36-9
표준 SMILES
C#CCC1=C(C)C(OC(=O)C2C(C=C(C)C)C2(C)C)CC1=O
InChIKey
SMKRKQBMYOFFMU-UHFFFAOYSA-N
분자식
C19H24O3
평균 분자량
300.4 g/mol
단동위원소 질량
300.17254462

개요

Prallethrin is a member of cyclopropanes and a terminal acetylenic compound. It has a role as an agrochemical and a pyrethroid ester insecticide. It is functionally related to a chrysanthemic acid.

이름 및 식별자

우선 이름
Prallethrin
IUPAC
(2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-en-1-yl) 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
영어명
Prallethrin
분자식
C19H24O3
분자량
300.39

이름 및 동의어

Prallethrin23031-36-9ETOCDTXSID0032572d,d-T80-PrallethrinCHEBI:39391DTXCID101965092-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl 2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropanecarboxylateCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propynyl)-2-cyclopenten-1-yl ester2X67A9B2Z7S-4068SFRefChem:868372
이름 더 보기
s4068PralleETOC(R)NYLAR(R)ai3-29750Propathrin
S-4068Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, cis,trans-(+)-, 2-methyl-4-oxo-3-(2-propynyl)-2-cyclopenten-1-yl esterCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-one, trans-(+-)-245-387-9D-PrallethrinPrallethrin(Mixture of diastereomers)S 4068S-4068 SF

데이터베이스 식별자

CAS
23031-36-9
PubChem CID

물성

구조 계산 물성

XLogP
4.3
극성 표면적
43.4 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
5
무거운 원자 수
22
형식 전하
0
복잡도
620

실험 및 물리화학적 성질

pHpH of a 1% aqueous emulsion is 6.1 at 20 °C
Pesticides · 3건

Pesticides

Pesticide

Pesticide (Prallethrin) -> USDA PDB

LogP · 2건

log Kow = 4.49 at 25 °C

4.49

Odor · 2건

Faint characteristic odor

Slightly phenolic odor

Density1.03 at 20 °C/4 °C
Viscosity0.550 Pa-s at 25 °C
Color/FormYellow to yellow brown liquid
Solubility · 5건

In water, 8 mg/L at 25 °C

In water, 8.51 ppm at 25 °C; Soluble in most organic solvents

In water, 8.03 mg/L at 25 °C and pH 5.5-5.6

In water, 4.88 mg/L at 20 °C

In hexane, methanol, xylene, >500 g/kg at 20-25 °C

Flash Point139 °C (282 °F) - closed cup
Endocrine DisruptorsPotential endocrine disrupting compound

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P301+P317, P304+P340, P316, P321, P330, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 3건

Hazard Traits - Environmental tox

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

Prallethrin: HSNO Approval: HSR003284 Approved with controls

FIFRA Requirements · 2건

(1) A tolerance of 1.0 ppm is established for residues of the insecticide prallethrin (RS)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1RS)-cis, trans-chrysanthemate as follows: (2) In or on food commodities in food handling establishments where food and food products are held, processed, prepared and/or served. (3) Application shall be limited to space, general surface, and spot and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and/or served. General surface or space spray applications may be used only when the facility is not in operation provided exposed food has been covered or removed from the area being treated prior to application. Spot and/or crack and crevice application may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Spray concentrate shall be limited to a maximum of 2.0% active ingredient. Contamination of food or food contact surfaces shall be avoided. Food contact surfaces and equipment should be throughly washed with an effective cleaning compound and rinsed with potable water after use of the product.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Prallethrin is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128722; Type of Pesticide: Conventional - insecticide; Use Site: Non-food/domestic, animals, industrial, commercial, and other non-food use; Year: 1995.

화학 및 산업

약리 정보

Mechanism of Action · 5건

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/

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 partical 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 increase sodium entry. /Pyrethroids/

(1) The interaction of a series of pyrethroid insecticides with the Na+ channels in myelinated nerve fibres of the clawed frog, Xenopus laevis, was investigated using the voltage clamp technique. (2) Out of 11 pyrethroids 9 insecticidally active compounds induce a slowly decaying Na+ tail current on termination of a step depolarization, whereas the Na+ current during depolarization was hardly affected. These tail currents are most readily explained by a selective reduction of the rate of closing of the activation gate in a fraction of the Na+ channels that have opened during depolarization. (3) The rate of decay of the Na+ tail current varies considerably with pyrethroid structure. After alpha-cyano pyrethroids the decay is at least one order of magnitude slower than after non-cyano pyrethroids. The decay always follows a single-exponential time course and is reversibly slowed when the temperature is lowered from 25 to 0 degrees C. Arrhenius plots in this temperature range are linear. (4) These results indicate that the relaxation of the activation gate in pyrethroid-affected Na+ channels is governed by an apparent first order, unimolecular process and that the rate of relaxation is limited by a single energy barrier. Application of transition state theory shows that after alpha-cyano pyrethroids this energy barrier is 9.6 kJ/mol higher than after non-cyano pyrethroids. (5) Differences in rate of decay of the Na+ tail current account for the reported differences in repetitive nerve activity induced by various pyrethroids. In addition, the effect of temperature on the rate of decay explains the increase in repetitive activity with cooling.. /Pyrethroids/

관련 반응

0건
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현재 필터 조건에 해당하는 반응 기록이 없습니다.

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
9839306
DTXSID
DTXSID0032572
ChEBI
CHEBI:39391
EC Number
245-387-9
Nikkaji
J23.765E
Boiling Point
313.5 °C at 760 mm Hg
Melting PointLiquid at room temperatures

물리화학적 성질

녹는점
25 °C · 25°C
끓는 점
381.62 °C · 381.62°C (rough estimate)
밀도
420 · d420 1.03
증기압
4.3 · ﹤4.3×10-5 Pa (23.1 °C)
굴절률
1.42 · 1.4200 (estimate)
인화점
139 °C · 139 °C
저장 조건
2 · 2-8°C
용해도
클로로포름(난용성), 에틸아세테이트(소량으로 용해), 메탄올(난용성)
수용성
8 mg · 8mg l-1(25°C)
Henry's Law Constant
6.2 · 6.2×100 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
안정적인. 강한 산화제와 호환되지 않습니다.
주요 응용
농업환경
InChI
1S/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3
InChIKey
SMKRKQBMYOFFMU-UHFFFAOYSA-N
SMILES
C\C(C)=C/C1C(C(=O)OC2CC(=O)C(CC#C)=C2C)C1(C)C
EPA
Prallethrin (23031-36-9)

화학적 성질

solid

DOT Emergency Guidelines · 5건

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Pyrethroid pesticide, liquid, flammable, poisonous;Pyrethroid pesticide, liquid, flammable, toxic; Pyrethroid pesticide, liquid, poisonous, flammable; Pyrethroid pesticide, liquid, toxic, flammable/

For more DOT Emergency Guidelines (Complete) data for Prallethrin (16 total), please visit the HSDB record page.

Toxic Combustion ProductsSpecial Hazards arising from the substance or mixture: Carbon oxides.
Hazard Classes and Categories · 3건

Acute Tox. 4 (100%)

Hazardous to the aquatic environment (acute) - category 1

Acute Tox. 3 *

Shipment Methods and Regulations · 3건

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials. /Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 °C; Pyrethroid pesticide, liquid, toxic; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 °C; Pyrethroid pesticide, solid toxic/

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article. /Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 °C; Pyrethroid pesticide, liquid, toxic; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 °C; Pyrethroid pesticide, solid toxic/

Shipping Name/ Number DOT/UN/NA/IMO · 5건

UN 3349; Pyrethroid pesticide, solid, toxic

UN 3350; Pyrethroid pesticide, liquid, flammable, toxic, flash point less than 23 degrees C

UN 3351; Pyrethroid pesticide, liquid, toxic, flammable, flash point not less than 23 degree C

UN 3352; Pyrethroid pesticide, liquid, toxic

For more Shipping Name/ Number DOT/UN/NA/IMO (Complete) data for Prallethrin (6 total), please visit the HSDB record page.

Skin, Eye, and Respiratory Irritations... May irritate the eyes. /Pyrethroids/

안전 및 보호

Fire Fighting Procedures · 3건

Wear self contained breathing apparatus for fire fighting if necessary.

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode.

Storage Conditions · 2건

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature: 2 - 8 °C.

Pyrethrins with piperonyl butoxide topical preparations should be stored in well-closed containers at a temperature less than 40 °C, preferably between 15-30 °C. /Pyrethrins/

Cleanup Methods · 3건

Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.

Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas.

Disposal Methods · 3건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.

Chemical packaging: Dispose of as unused product.

Preventive Measures · 4건

Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.

Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.

Control of environmental exposure: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

Allowable Tolerances · 1건

(1) A tolerance of 1.0 ppm is established for residues of the insecticide prallethrin (RS)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1RS)-cis, trans-chrysanthemate as follows: (2) In or on food commodities in food handling establishments where food and food products are held, processed, prepared and/or served. (3) Application shall be limited to space, general surface, and spot and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and/or served. General surface or space spray applications may be used only when the facility is not in operation provided exposed food has been covered or removed from the area being treated prior to application. Spot and/or crack and crevice application may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Spray concentrate shall be limited to a maximum of 2.0% active ingredient. Contamination of food or food contact surfaces shall be avoided. Food contact surfaces and equipment should be throughly washed with an effective cleaning compound and rinsed with potable water after use of the product.

Personal Protective Equipment (PPE) · 5건

Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Skin protection: Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/

Body protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.

For more Personal Protective Equipment (PPE) (Complete) data for Prallethrin (6 total), please visit the HSDB record page.

독성 정보

Interactions · 3건

The effects of pyrethroids were studied on phosphoinositide breakdown in guinea pig synaptoneurosomes. Similar to other agents that activate voltage-dependent sodium channels, type I and type II pyrethroids stimulated phosphoinositide breakdown. Type II pyrethroids, like deltamethrin and fenvalerate, were more potent and, at least for deltamethrin, more efficacious than type I pyrethroids, like allethrin, resmethrin and permethrin. The effects of type II pyrethroids could be partially inhibited by the sodium channel blocker tetrodotoxin. The effects of allethrin and resmethrin were not affected by 5 microM tetrodotoxin. Stimulation of phosphoinositide breakdown by fenvalerate was additive to the stimulation elicited by the receptor agonists carbamylcholine and norepinephrine, but not to the stimulation elicited by sodium channel agents (batrachotoxin, scorpion venom and pumiliotoxin B). Stimulation by allethrin was not additive to the stimulation elicited either by receptor agonists or sodium channel agents. A submaximal concentration of allethrin, a type I pyrethroid, did not greatly affect the dose-dependent stimulation elicited by a type II pyrethroid, deltamethrin, while a higher concentration of allethrin prevented further stimulation by type II pyrethroids. A local anesthetic, dibucaine, which inhibits sodium channel activation, inhibited phosphoinositide breakdown induced by type II, but not by type I pyrethroids, except at higher concentrations. Thus, type II pyrethroids appear to stimulate phosphoinositide breakdown in synaptoneurosomes in a manner analogous to other sodium channel agents, while type I pyrethroids elicit phosphoinositide breakdown by a different mechanism, probably not involving sodium channels.

/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/

Ecotoxicity Values · 5건

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 10 days; diet (chemical incorporated into food) >5620 ppm for 8 days

LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 19 wk; oral via capsule 1171 mg/kg (95% confidence interval: 835-1835 mg/kg)

LC50; Species: Anas platyrhynchos (Mallard Duck) age 10 days; diet (chemical incorporated into food) >5620 ppm for 8 days

LD50; Species: Anas platyrhynchos (Mallard Duck) age 19 wk; oral via capsule >1000 mg/kg

For more Ecotoxicity Values (Complete) data for Prallethrin (13 total), please visit the HSDB record page.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), reported Koc values of 1,318(2) and 2,533(3), and an estimated Koc value of 3082(SRC), determined from a structure estimation method(4), indicates that prallethrin is expected to have low to slight mobility in soil(SRC). Volatilization of prallethrin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC) estimated from its vapor pressure, 3.5X10-5 mm Hg(5), and water solubility, 8 mg/L(6), in combination with strong soil adsorption. Prallethrin is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. The photodegradation half-life of prallethrin on soil surfaces was measured as 24.8-26.9 days using EPA Guideline 161-3(7). Using an unspecifed aerobic biodegradation test, prallethrin was found to be not biodegradable in 28 days(8), suggesting that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 1,318(2) and 2,533(3), and an estimated Koc value of 3082(SRC), determined from a structure estimation method(4), indicates that prallethrin is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is possible(5) based upon an estimated Henry's Law constant of 1.6X10-6 atm-cu m/mole(SRC), derived from its vapor pressure, 3.5X10-5 mm Hg(6), and water solubility, 8 mg/L(7). Using this Henry's Law constant and an estimation method(5), volatilization half-lives for a model river and model lake are 40 and 299 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 approximately 10 years if adsorption is considered(8). According to a classification scheme(9), a measured BCF of 1,160 in Bluegill fish (Lepomis macrochirus)(10) suggests the potential for bioconcentration in aquatic organisms is very high(SRC). The photolysis half-life of prallethrin in sterile water at 22 to 27 °C at pH 5 in natural sunlight was 13.6 hours(11). The hydrolysis half-life of prallethrin at pH 9 and 23.5-25 °C was measured as 118 hours(11); significant degradation was not observed during 30 days a pH 5 or pH 7(11). Using an unspecifed aerobic biodegradation test, prallethrin was found to be not biodegradable in 28 days(12), suggesting that biodegradation is not an important environmental fate process in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), prallethrin, which has a vapor pressure of 3.5X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase prallethrin 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 2 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase prallethrin is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be 18 minutes(SRC), calculated from its rate constant of 9.1X10-16 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Prallethrin directly photolyzes when exposed to sunlight(4). Particulate-phase prallethrin may be removed from the air by wet and dry deposition(SRC).

Average Daily IntakeThe acute and chronic dietary exposure and risk for prallethrin to the US general population (maximally exposed) has been reported as a 0.022822 mg/kg/day acute exposure and a 0.000879 mg/kg/day chronic exposure(1).
Ongoing Test Status · 1건

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; See the data in Chemical Explorer/[USEPA; ICSS Dashboard Application; Available from, as of March 28, 2014: http://actor.epa.gov/dashboard/]

Soil Adsorption/Mobility · 1건

Koc values of 1,318(1) and 2,533(2) have been reported for prallethrin. Using a structure estimation method based on molecular connectivity indices(3), the Koc of prallethrin can be estimated to be 3082(SRC). According to a classification scheme(4), these Koc values suggests that prallethrin is expected to have low to slight mobility in soil. Prallethrin is reported to be readily adsorbed into soil(5). Very little movement of prallethrin through soil columns was observed using radio-labeled material(6).

Atmospheric Concentrations · 1건

INDOOR AIR: Air samples collected from an indoor room within 30-45 minutes after application of an aerosol insecticide containing prallethrin had a prallethrin concentration of 0.0138 ppm(1); after 6 hours, air residue levels were <0.0001 ppm(1).

Human Toxicity Excerpts · 5건

/HUMAN EXPOSURE STUDIES/ Changes in biochemical composition in erythrocyte membrane, erythrocytic osmotic haemolysis, and nitrite and nitrate levels in plasma were analyzed in 12 human volunteers who were exposed regularly to prallethrin, a type I pyrethroid mosquito repellent. The results revealed a decrease in cholesterol (C) and phospholipid (P) moieties in erythrocyte membrane with no consequent change in C:P ratio. Further, a significant decrease in the content of phosphatidyl serine suggested that PS is a sensitive phospholipid species to the pyrethroid action. Significant decrease in membrane lipid peroxidation and enhanced levels of nitrite and nitrate in plasma and erythrocyte indicate that increased generation and availability of nitric oxide might have rendered tolerance to erythrocyte membrane by protecting the cells from hemolysis. Increased NO(2) and NO(3) may be due to increased activity of nitric oxide synthase (NOS) and/or expression of isoforms of NOS. A possible involvement of free radical scavenging and antioxidant effects of nitric oxide might have contributed to the observed decrease in lipid peroxidation in the present study.

/HUMAN EXPOSURE STUDIES/ Continuous exposure of humans to pyrethroid-based mosquito repellents for longer durations may lead to adverse health effects. No information is available on long-term use of these mosquito repellents pertaining to the biochemical changes in human subjects. Therefore, the present study is an attempt to evaluate the status of health in human volunteers exposed to two commercially available mosquito repellent pyrethroids, allethrin and prallethrin, in terms of changes in plasma biochemical profile. Results of this study showed less but significant increase in the levels of plasma glucose, phospholipids, nitrite and nitrate, lipid peroxides with a decrease in plasma cholesterol. No significant changes were observed in the contents of total protein, albumin, globulin, HDL-C /(High-density lipoprotein-C)/ and LDL-C /(Low-density lipoprotein-C)/. However, SGPT /(Serum glutamate pyruvate transaminase)/ activity increased significantly in persons exposed to only allethrin. Though the present investigation involving a limited number of human subjects indicates the onset of both protective changes as well as derangement in metabolism, a detailed and rigorous study is greatly warranted to arrive at a definite conclusion about the effects of pyrethroid mosquito repellents.

/HUMAN EXPOSURE STUDIES/ In Sweden 33% of workers polled reported skin and eye irritation following occupational exposure.

/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/

Artificial Pollution SourcesPrallethrin'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).
Environmental BiodegradationAEROBIC: According to the MSDS of one prallethrin manufacturer(1), prallethrin was found to be not biodegradable under the test conditions within 28 days (test conditions and method not reported).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Environmental Bioconcentration · 1건

A log BCF of 3.0645 (BCF of 1,160) was measured in Bluegill fish (Lepomis macrochirus) using a 28-day flow-through tank exposure method(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is very high(SRC).

규제 정보

FIFRA Requirements · 2건

(1) A tolerance of 1.0 ppm is established for residues of the insecticide prallethrin (RS)-2-methyl-4-oxo-3-(2-propynyl)cyclopent-2-enyl (1RS)-cis, trans-chrysanthemate as follows: (2) In or on food commodities in food handling establishments where food and food products are held, processed, prepared and/or served. (3) Application shall be limited to space, general surface, and spot and/or crack and crevice treatment in food handling establishments where food and food products are held, processed, prepared and/or served. General surface or space spray applications may be used only when the facility is not in operation provided exposed food has been covered or removed from the area being treated prior to application. Spot and/or crack and crevice application may be used while the facility is in operation provided exposed food is covered or removed from the area being treated prior to application. Spray concentrate shall be limited to a maximum of 2.0% active ingredient. Contamination of food or food contact surfaces shall be avoided. Food contact surfaces and equipment should be throughly washed with an effective cleaning compound and rinsed with potable water after use of the product.

New Active Ingredients ... includes chemicals not previously registered as pesticides, as well as pesticide active ingredients initially registered after November 1, 1984 and that currently have active product registrations. By law, these pesticides must meet new safety standards, such as those described in the Food Quality Protection Act of 1996 and, if new safety standards are met, will be reviewed again on a 15-year cycle. Prallethrin is designated by EPA as a New Pesticide Active Ingredient. Active Ingredient Number: 128722; Type of Pesticide: Conventional - insecticide; Use Site: Non-food/domestic, animals, industrial, commercial, and other non-food use; Year: 1995.

안전 데이터

wgk
3
ridadr
UN2811 6.1/PG 2
독성
mouse,LD50,oral,190mg/kg (190mg/kg),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 228, 1989.
HS 번호
29162090
risk_code
22-23-50/53
hazard_code
T,N
safety_code
45-60-61
기존화학 물질
KE-24678
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
스토리지 클래스
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
유해 물질 데이터
23031-36-9(Hazardous Substances Data)

Type I Pyrethroid esters /lacking the alpha-cyano substituents/ affect sodium channels in nerve membranes, causing repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential, the effects being quite similar to those produced by DDT /dichlorodiphenyltrichloroethane/. /Pyrethroid esters lacking the alpha-cyano substituent/

For more Mechanism of Action (Complete) data for Prallethrin (6 total), please visit the HSDB record page.

Metabolism/Metabolites · 5건

The major biotransformation reactions of prallethrin are summarized as follows: (1) oxidation at the methyl group of the isobutenyl group in the acid moiety; (2) hydroxylation at the C-1 or C-2 position of the propynyl group in alcohol moiety; (3) cleavage of the ester linkage; and (4) conjugation of resulting metablites; with glucoronic acid, sulfuric acid, or mercapturic acid.

On single oral or subcutaneous administration of (4S, 1R)-trans-or (4S,1R)-cis-prallethrin labeled with (14)C in the alcohol moiety to rats at 2mg/kg, 96-104% of the dosed (14)C was eliminated into urine and feces within 7 days after administration. Monitoring of the expired air indicated that less than 0.1% of the dose was excreted as (14)CO2. ... Nineteen metabolites were identified in urine and feces. Two new types of S_linked conjugation (sulfonic acid and mercapturic acid types) were additionally identified.

The relative resistance of mammals to the pyrethroids is almost wholly attributable to their ability to hydrolyze the pyrethroids rapidly to their inactive acid and alcohol components, since direct injection into the mammalian CNS leads to a susceptibility similar to that seen in insects. Some additional resistance of homeothermic organisms can also be attributed to the negative temperature coefficient of action of the pyrethroids, which are thus less toxic at mammalian body temperatures, but the major effect is metabolic. Metabolic disposal of the pyrethroids is very rapid, which means that toxicity is high by the iv route, moderate by slower oral absorption, and often unmeasureably low by dermal absorption. /Pyrethroids/

Fastest breakdown is seen with primary alcohol esters of trans-substituted acids since they undergo rapid hydrolytic and oxidative attack. For all secondary alcohol esters and for primary alcohol cis-substituted cyclopropanecarboxylates, oxidative attack is predominant. /Pyrethroids/

The ... pyrethroids are readily metabolized in animals and man by hydrolases and the CYP microsomal system. The metabolites are of lower toxicity than the parent compounds.

Absorption, Distribution and Excretion · 2건

On single oral or subcutaneous administration of (4S, 1R)-trans-or (4S,1R)-cis-prallethrin labeled with (14)C in the alcohol moiety to rats at 2mg/kg, 96-104% of the dosed (14)C was eliminated into urine and feces within 7 days after administration. Monitoring of the expired air indicated that less than 0.1% of the dose was excreted as (14)CO2. ... Urine excretion of (14)C with the trans isomer was larger (60 - 78%) than the cis isomer (17-32%), where as (14)C fecal excretion with the trans isomer was smaller than that with the cis isomer. (14)C levels in blood and other tissues reached maxium within 3 hr after oral administration and thereafter decreased rapidly. (14)C tissue residues were generally very low on the 7th day after administration.

The pyrethroids and pyrethrins are lipophilic and as such are rapidly distributed to the CNS. /Pyrethroids and pyrethrin/

용도 및 제조

Uses · 3건

For prallethrin (USEPA/OPP Pesticide Code: 128722) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Flying and crawling insect control for industrial locations and outdoor use.

Prallethrin is a synthetic pyrethroid with fast knock-down activity against household insect pests. It is used in household insecticide products against mosquitoes, houseflies and cockroaches. Prallethrin also has veterinary uses in the treatment of domestic pets.

Formulations/Preparations · 5건

Aerosol, emulsifiable concentrate, mosquito coil/mat, vaporizer liquid, oil liquid.

Commercially formulated as a mixture of (4S,1R)-trans and (4S,1R)-cis isomers in a ratio of approximately 4:1.

Ortho Roach, Ant and Spider Killer (The Scotts Company): Active ingredient: MGK 264 0.2870%; esfenvalerate 0.0500%; and prallethrin 0.0300%.

Ortho Roach, Ant and Spider Killer (The Scotts Company): Active ingredient: prallethrin 0.0300% and bifenthrin 0.0500%.

For more Formulations/Preparations (Complete) data for Prallethrin (78 total), please visit the HSDB record page.

Household ProductsInformation on 63 consumer products that contain Prallethrin in the following categories is provided:
General Manufacturing Information · 2건

The WHO Recommended Classification of Pesticides by Hazard identifies prallethrin (technical grade) as Class II: moderately hazardous; Main Use: insecticide.

Synthetic pyrethroid; propynyl analog of allethrin. Of the 8 possible stereoisomers, the (4S,1R)-trans isomer has the most insecticidal activity.

응용 분야

용도Prallethrin ia a synthetic pyrethroid; propynyl analog of allethrin. Prallethrin is used as an insecticide.

상·하류 제품 정보

상류 원료

아세트초산에틸메틸 글리옥살에틸알코올N,N-다이메틸폼아마이드프로파르길벤젠설폰산염나트륨 에톡시드Acetylacetone6-Heptynoic acid헥신초산에틸캠아줄렌

공급사74 곳

Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
湖北威德利化学试剂有限公司186-02735115 18062128043 · [email protected]
Hebei Zhuanglai Chemical Trading Co Ltd+86-16264648883 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
Hubei Lidu New Material Technology Co., Ltd+86-19307248857 +86-19307248857 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
河北枫嘉新材料科技有限公司+86-0311-87836622 +86-18712993135 · [email protected]
Syntechem Co.,Ltd[email protected]
上海德默医药科技有限公司400-021-7337 2355568890 · [email protected]
武汉市恒久化工有限公司17317534732 17671758929 · [email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
湖北魏氏化学试剂股份有限公司027-59102966 18717199209 · [email protected]
上海艾梯西生物科技有限公司18721763493 · [email protected]
医恩医疗系统研发(上海)有限公司021-58958002 18930822973 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
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四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
Hebei Zhuanglai Chemical Trading Co.,Ltd13343047651 · [email protected]
TargetMol 中国(陶术生物)400-821-0310 15002144251 · [email protected]
成都麦卡希化工有限公司028-85632863 18108198598 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
PT CHEM GROUP LIMITED+86-85511178; +86-85511178 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
天津阿尔塔科技有限公司022-65378550-8551 · [email protected]
Shijiazhuang Jianxin Biotechnology Co., LTD+undefined-86-1906231316-9 +86-19062313169 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
湖北赛恩斯化工有限公司15994282563 15994282563 · [email protected]
Henan Alfa Chemical Co., Ltd+8618339805032 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
广东翁江化学试剂有限公司0751-2886766 13927870850 · [email protected]
湖北万业众诚化学试剂有限责任公司18671296875 · [email protected]
南通市苏北化工原料有限公司0513-85290972 18762756250 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海鑫矽新材料有限公司13585834793 13660927110 · [email protected]
南京罗迈美生物科技有限公司[email protected]
Hubei Langyou International Trading Co., Ltd+86-12345678900 +86-18874586545 · [email protected]
Shaanxi Dideu New Materials Co. Ltd18192503167 · [email protected]
陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]
河南中梵实业发展有限公司+86-18906033525 · [email protected]
上海泰坦科技股份有限公司13023226327 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]

For more Human Toxicity Excerpts (Complete) data for Prallethrin (7 total), please visit the HSDB record page.