基本情報
- CAS
28057-48-9- 標準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- 分子式
- C19H26O3
- 平均分子量
- 302.4 g/mol
- 単同位体質量
- 302.18819469
概要
D-trans-allethrin is a clear to amber viscous liquid. A synthetic insecticide structurally similar to pyrethrin.
名称と識別子
- 優先名称
- 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
- 現地名
- rel-2,2-ジメチル-3β*-(2-メチル-1-プロペニル)シクロプロパン-1α*-カルボン酸2-メチル-4-オキソ-3-(2-プロペニル)-2-シクロペンテン-1α*-イル
- 英語名
- ALLETHRINS
- 分子式
- C19H26O3
- 分子量
- 302.41
名称と別名
S-BIOALLETHRINEsbiolEsbioallethrinEsdepallethrinetrans-(+)-AllethrinWasp Killer IId-T-Allethrind-Allethrolone chrysanthemumateCaswell No. 025ADTXSID2039336GFF4AL7FRMUNII-GFF4AL7FRM
名称をさらに表示
rel-2,2-ジメチル-3β*-(2-メチル-1-プロペニル)シクロプロパン-1α*-カルボン酸2-メチル-4-オキソ-3-(2-プロペニル)-2-シクロペンテン-1α*-イルα-DL-trans-アレトリン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-
物性
構造計算による物性
- XLogP
- 4.8
- 極性表面積
- 43.4 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 22
- 形式電荷
- 0
- 複雑度
- 573
実験および物理化学的性質
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Pesticides
Pesticides -> Pyrethrins/Pyrethroids
Pesticide (S-Bioallethrin) -> USDA PDB
DensityRelative density (water = 1): 0.98
SolubilitySolubility in water: none
Flash Point~120 °C
Physical Description
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]
物理化学的性質
- 融点
- 50 · 50-51 °C
- 沸点
- 386.8 · 386.8±42.0 °C(Predicted)
- 比重(密度)
- 1.05 · 1.05±0.1 g/cm3(Predicted)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
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)
危険有害性情報
Regulatory Information
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
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
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]
化学と産業
薬理情報
Metabolism/Metabolites
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.
用途と製造
Uses
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
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