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S-Bioallethrin

HCID 62829
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
28057-48-9
Standard SMILES
C=CCC1=C(C)[C@@H](OC(=O)[C@@H]2[C@@H](C=C(C)C)C2(C)C)CC1=O
InChIKey
ZCVAOQKBXKSDMS-PVAVHDDUSA-N
Molecular formula
C19H26O3
Average molar mass
302.4 g/mol
Monoisotopic mass
302.18819469

Overview

D-trans-allethrin is a clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin.

Names & identifiers

Preferred name
S-Bioallethrin
IUPAC
cis-[(1S)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate
English name
ALLETHRINS
Molecular formula
C19H26O3
Molecular weight
302.41

Names & synonyms

S-BIOALLETHRINEsbiolEsbioallethrinEsdepallethrinetrans-(+)-AllethrinWasp Killer IId-T-Allethrind-Allethrolone chrysanthemumateCaswell No. 025ADTXSID2039336GFF4AL7FRMUNII-GFF4AL7FRM
Show more names
α.-DL-trans-Allethrinalpha-Dl-trans-allethrin3-(2-propenyl)-2-methyl-4-oxo-2-cyclopentenyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylateCyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, ster with 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one, trans-(+-)-Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, (1R)-2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, (1R,3R)-rel-Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, (1R)-2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl ester, (1R,3R)-rel-
AI 3-29024EINECS 249-013-5d-Allethrolone d-trans-chrysanthemumateBRN 2059862RU 16121RU-16121(+)-Allethronyl (+)-trans-chrysanthemumateDTXCID0019336

Properties

Computed structural properties

XLogP
4.8
Topological polar surface area
43.4 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
22
Formal charge
0
Complexity
573

Experimental & physicochemical properties

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Pesticides · 2 items

Pesticides -> Pyrethrins/Pyrethroids

Pesticide (S-Bioallethrin) -> USDA PDB

DensityRelative density (water = 1): 0.98
SolubilitySolubility in water: none
Flash Point~120 °C
Physical Description · 3 items

D-trans-allethrin is a clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin.

Yellow liquid with a mild aromatic odor; [EXTOXNET]

YELLOW VISCOUS LIQUID.

Collision Cross Section184.5 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID2039336]

Physicochemical properties

Safety & regulation

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

GHS classification

GHS Classification · 6 items

Warning

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

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

Warning

H302 (48.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, P391, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 2 items

Esbioallethrin: HSNO Approval: HSR005179 Approved with controls

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

Other Safety InformationIMAP assessments - Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester, [1R-[1.alpha.(S*),3.beta.]]-: Environment tier I assessment
DOT LabelClass 9
Fire Hazards · 2 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Combustible. Liquid formulations containing organic solvents may be flammable.

Health HazardsExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Hazards Summary · 1 item

Slightly toxic after skin absorption or ingestion with an oral LD50 of 1100 mg/kg in male rats; Liver injury is detected in animal experiments with high oral doses. [EXTOXNET] See Bioallethrin, RN: 584-79-2, with LCLo (rats) = 13,800 mg/m3/4H and a vapor pressure = 0.0000012 mm Hg. [ChemIDplus] Pyrethroids have low toxicity to humans after dermal exposure. Of 573 dermal or ingestion poisoning cases in China, 51 patients had disturbed consciousness and 34 had seizures. Of those, only five were occupationally exposed. Seizures are more commonly related to exposures to fenvalerate, flucythrinate, cypermethrin, deltapermethrin, and fluvalinate. Seizures have not been reported after exposure to permethrin. Pyrethroids may also cause paresthesias after skin contact. Paresthesias (stinging and numbness) usually begin 1-2 hours after contact and resolve within 24 hours. [EPA Pesticides, p. 87-8] Pyrethrins cause liver injury when fed to animals at high doses. [EXTOXNET]

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

S-Bioallethrin has known human metabolites that include [(1S)-2-methyl-4-oxo-3-prop-2-enylcyclopent-2-en-1-yl] (1R,3R)-3-[(Z)-3-hydroxy-2-methylprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate.

Upon absorption of allethrine , biotransformation takes place through hydrolysis of the central ester bond, oxidative attacks at several sites, and conjugation reactions to produce a complex array of primary and secondary water-soluble metabolites that undergo urinary and biliary excretion. Allethrin is oxidized not only at the chrysanthemate isobutenyl moiety to the corresponding primary alcohol but also at the allyl group to 1'-hydroxyprop-2'-enyl and 2',3'-dihydroxy-propyl derivatives, or at a methyl group on the cyclopropyl moiety to a hydroxy derivative. It is widely accepted that metabolism results in the formation of compounds that have little or no demonstrable toxicity, although the formation of reactive or toxic intermediates cannot be ruled out, and it appears that cleavage of the ester bond results in substantial detoxification. Allethrin is also converted to chrysanthemum dicarboxylic acid and allethrolone. Allethrin leaves the body quickly, mainly in the urine, but also in feces and breath. (L857, A558)

MeSH Pharmacological ClassificationPesticides 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.

Uses & manufacturing

Uses · 3 items

Used in homes and gardens to kill flies and mosquitoes; The d-trans isomer is a more potent insecticide used to control animal parasites. Sold as mosquito coils, mats, oil formulations, and sprays; [EXTOXNET]

Farming (Pesticides) [Category: Industry]

Pyrethroids are used as insecticides. (L857)

Household ProductsInformation on 9 consumer products that contain d-trans-Allethrin in the following categories is provided:
Use Classification

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
28057-48-9、28434-00-6、3972-20-1
PubChem CID
62829
DTXSID
DTXSID2039336
ChEMBL
CHEMBL1887350
ChEBI
CHEBI:39115
UNII
GFF4AL7FRM、Y8J603E78R
EC Number
249-013-5
Nikkaji
J16.996J
Melting point
50 · 50-51 °C
Boiling point
386.8 · 386.8±42.0 °C(Predicted)
Density
1.05 · 1.05±0.1 g/cm3(Predicted)
FDA UNII
8 J603E78R · Y8J603E78R
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
EC ClassificationSymbol: Xn, N; R: 20/22-50/53; S: (2)-36-60-61; Note: C
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Reactivity ProfileD-TRANS-ALLETHRIN is incompatible with alkalis.
Chemical DangersDecomposes above 400 °C . This produces irritating fumes.
Packaging and LabellingDo not transport with food and feedstuffs.

Safety & protection

Fire Fighting · 2 items

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:

Use powder, AFFF, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 items

Fresh air, rest. Refer for medical attention.

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.

Rinse mouth.

First AidExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Safe StorageProvision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Keep in a well-ventilated room.
Nonfire Spill ResponseExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Spillage Disposal · 1 item

Personal protection: filter respirator for organic gases and particulates adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Do NOT wash away into sewer. 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.

Isolation and EvacuationExcerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Eye PreventionWear safety goggles.
Fire PreventionNO open flames.
Inhalation RiskNo 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.
Skin PreventionProtective gloves.
Exposure PreventionPREVENT GENERATION OF MISTS!

Toxicology

Treatment · 1 item

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, Remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (L363)

Health Effects · 1 item

As for every type I pyrethroid, allethrin effects typically include rapid onset of aggressive behavior and increased sensitivity to external stimuli, followed by fine tremor, prostration with coarse whole body tremor, elevated body temperature, coma, and death. Paresthesia can also occur after dermal exposure to allethrin. It is likely to be a human carcinogen by the oral route. (L857)

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2 items

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Inhalation (L858) ; oral (L858) ; dermal (L858) ; eye contact (L858).

Toxicity Summary · 1 item

Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)

Signs and Symptoms · 4 items

Cough.

Redness.

Redness.

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

Acute Toxicity Link · 2 items

Chemical: DOWICIL 75

Chemical: S-BIOALLETHRIN

ICSC Environmental DataThe substance is very toxic to aquatic organisms. This substance does enter the environment under normal use. Great care, however, should be taken to avoid any additional release, for example through inappropriate disposal.
Carcinogen Classification · 2 items

Not listed by IARC.

No indication of carcinogenicity to humans (not listed by IARC).

Toxicity DataLD50: 1100 mg/kg (Oral, Rat) (L859) LD50: 480 mg/kg (Oral, Mouse) (L859) LD50: >2500 mg/kg (Dermal, Rat) (L859)
· 2 items

ANTIMICROBIAL AGENTS

INSECTICIDES

Additional notes

DefinitionChEBI: Allethrin is a cyclopropanecarboxylate ester. It has a role as a pyrethroid ester insecticide. It is functionally related to a chrysanthemic acid.