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Substance Name: Allethrin [BSI:ISO]
RN: 584-79-2
InChIKey: ZCVAOQKBXKSDMS-AQYZNVCMSA-N

Notes

  • Isomer blend of the allethrin series rich in D-allethrolone ester of chrysanthemic acid.
  • Synthetic analogs of the naturally occurring insecticides cinerin, jasmolin, and pyrethrin. (From Merck Index, 11th ed)

Molecular Formula

  • C19-H26-O3

Molecular Weight

  • 302.4114
 

Classification Codes

  • Agricultural Chemical
  • Insecticide
  • Insecticides
  • Mutation Data
  • Pesticides
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Names and Synonyms

Results Name

  • Allethrin [BSI:ISO]

Name of Substance

  • Allethrin [BSI:ISO]
  • Allethrins
  • Bioallethrin [BAN]
  • Esbiothrin

MeSH Heading

  • Allethrin

Synonyms

  • (+)-Allelrethonyl (+)-cis,trans-chrysanthemate
  • (+)-trans-Chrysanthemumic acid ester of (+-)-allethrolone
  • (+-)-Allerethonyl (+-)-cis,trans-chrysanthemate
  • (RS)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl (+-)-cis,trans-chrysanthemate
  • 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester
  • 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid, ester with 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one
  • 2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one ester of chrysanthemummono-carboxylic acid
  • 2-Methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecar
  • 3-Allyl-2-methyl-4-oxo-2-cyclopenten-1-yl chrysanthemate
  • 3-Allyl-4-keto-2-methylcyclopentenyl chrysanthemummonocarboxylate
  • 3-Allyl-4-methyl-2-oxo-3-cyclopenten-1-yl ester of 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid
  • AI3-17510
  • Allethrin
  • Allethrin I
  • Allethrine
  • Allethrine [ISO-French]
  • Allethrolone ester of chrysanthemummonocarboxylic acid
  • Allyl cinerin I
  • Allyl homolog of cinerin I
  • Allylrethronyl dl-cis-trans-chrysanthemate
  • Binamin forte
  • Bioaletrina
  • Bioaletrina [Portuguese]
  • Bioallethrin
  • Bioallethrin [BSI]
  • Bioaltrina
  • Bioaltrina [Portuguese]
  • Caswell No. 025
  • CCRIS 2494
  • Cinerin I allyl homolog
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopentene-1-yl ester
  • d,l-2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one-d,l-chrysanthemum monocarboxylate
  • d-Allethrin
  • Depallethrin
  • dl-2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one ester of d-trans-2,2-dimethyl-3-(2-methylpropenyl)
  • dl-2-Allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one ester of dl cis/trans 2,2-dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylic acid
  • dl-3-Allyl-2-methyl-4-oxocyclopent-2-enyl dl-cis trans chrysanthemate
  • EINECS 209-542-4
  • ENT 17,510
  • EPA Pesticide Chemical Code 004001
  • EPA Pesticide Chemical Code 004003
  • Esbiol TM Intermediate 3336
  • Exthrin
  • FDA 1446
  • FMC 249
  • HSDB 1511
  • Matox
  • Necarboxylic acid
  • NIA 249
  • NSC 11782
  • OMS 3045
  • Pallethrine
  • Pynamin
  • Pynamin-forte
  • Pyresin
  • Pyresyn
  • Pyrethrin
  • RU 27436
  • trans-Allethrin
  • UNII-0X03II877M
  • UNII-G79DM7O471
  • Wasp Stopper CF

Systematic Names

  • (RS)-3-Allyl-2-methyl-4-oxocyclopent-2-enyl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
  • 2-Cyclopenten-1-one, 2-allyl-4-hydroxy-3-methyl-, 2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylate
  • Allethrin
  • Bioallethrin
  • Chrysanthemummonocarboxylic acid, 3-allyl-3-methyl-4-oxo-2-cyclopenten-1-yl ester
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propen-1-yl)-, 2-methyl-4-oxo-3-(2-propen-1-yl)-2-cyclopenten-1-yl ester
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-, 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester
  • Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methylpropenyl)-, ester with 2-allyl-4-hydroxy-3-methyl-2-cyclopenten-1-one (VAN) (8CI)
  • Esbiothrin

Superlist Names

  • Allethrin
  • Allethrin coil

Registry Numbers

CAS Registry Number

  • 584-79-2

FDA UNIIs

  • 0X03II877M
  • G79DM7O471

Other Registry Numbers

  • 137-98-4
  • 18793-35-6
  • 18877-88-8
  • 20301-61-5
  • 22431-63-6
  • 22556-34-9
  • 23453-08-9
  • 24313-23-3
  • 25406-22-8
  • 25406-24-0
  • 25406-25-1
  • 6385-67-7
  • 6385-68-8
  • 71119-51-2
  • 71211-88-6
  • 8018-12-0
  • 84030-86-4

System Generated Number

  • 0000584792

Structure Descriptors

InChI

1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3/t14-,16?,17+/m1/s1

InChIKey

ZCVAOQKBXKSDMS-AQYZNVCMSA-N

Smiles

CC(=C[C@@H]1[C@@H](C(=O)OC2CC(=O)C(=C2C)CC=C)C1(C)C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LC50 inhalation > 2gm/m3 (2000mg/m3)   Yakkyoku. Pharmacy. Vol. 37, Pg. 187, 1986.
mouse LD50 intraperitoneal 38mg/kg (38mg/kg)   Journal of Agricultural and Food Chemistry. Vol. 31, Pg. 250, 1983.
mouse LD50 oral 370mg/kg (370mg/kg)   Agricultural and Biological Chemistry. Vol. 28, Pg. 914, 1965.
mouse LD50 skin 1200mg/kg (1200mg/kg)   Agricultural and Biological Chemistry. Vol. 27, Pg. 684, 1963.
mouse LDLo intracrebral 4mg/kg (4mg/kg)   Toxicology and Applied Pharmacology. Vol. 66, Pg. 290, 1982.
quail LD50 oral 2030mg/kg (2030mg/kg)   Pesticide Manual. Vol. 9, Pg. 19, 1991.
rabbit LD50 intraperitoneal 11200mg/kg (11200mg/kg)   World Review of Pest Control. Vol. 3, Pg. 28, 1964.
rabbit LD50 oral 4290mg/kg (4290mg/kg)   Special Publication of the Entomological Society of America. Vol. 78-1, Pg. 7, 1978.
rabbit LD50 skin 11332mg/kg (11332mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: TREMOR
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 2, Pg. 420, 1950.
rat LCLo inhalation 13800mg/m3/4H (13800mg/m3) BEHAVIORAL: TREMOR

BEHAVIORAL: EXCITEMENT
AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 2, Pg. 420, 1950.
rat LD50 oral 685mg/kg (685mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C255, 1991.
rat LD50 skin 2500mg/kg (2500mg/kg)   Yakkyoku. Pharmacy. Vol. 37, Pg. 187, 1986.
rat LD50 unreported 680mg/kg (680mg/kg)   "Chemistry of Pesticides," Melnikov, N.N., New York, Springer-Verlag New York, Inc., 1971Vol. -, Pg. 131, 1971.
rat LDLo intravenous 4mg/kg (4mg/kg) BEHAVIORAL: AGGRESSION

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pesticide Biochemistry and Physiology. Vol. 2, Pg. 308, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point -4.00E+01 deg C   EXP
log P (octanol-water) 4.78 (none)   EXP
Water Solubility 4.6 mg/L 25 EXP
Vapor Pressure 1.20E-06 mm Hg 21 EXP
Henry's Law Constant 1.04E-07 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.25E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.