Allethrins
Title: Allethrins
Additional Names: Allyl cinerins
Literature References: Synthetic analogs of the naturally occurring insecticides cinerins, jasmolins, and pyrethrins, q.q.v. Review: Barthel, World Rev. Pest Control 6, 59 (1967); World Health Org., Environ. Health Criter. 87, 1-75 (1989). Review of toxicology and human exposure: Toxicological Profile for Pyrethrins and Pyrethroids (PB2004-100004, 2003) 332 pp.
 
Derivative Type: Allethrin I
CAS Registry Number: 584-79-2
Additional Names: 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester; allethrolone ester of chrysanthemummonocarboxylic acid
Trademarks: Pynamin (Sumitomo)
Molecular Formula: C19H26O3
Molecular Weight: 302.41
Percent Composition: C 75.46%, H 8.67%, O 15.87%
Literature References: Synthesis: M. S. Schechter et al., J. Am. Chem. Soc. 71, 1517, 3165 (1949); H. A. Stansbury, H. R. Guest, US 2768965 (1956 to UCC). Commercial process: H. J. Sanders, A. W. Taff, Ind. Eng. Chem. 46, 414 (1954).
Properties: The commercial product is a mixture of 8 optically active isomers. Clear, pale yellow oil. bp 0.1 140°. Decomp by rapid pyrolysis at >400°. Vaporizes without dec when heated at 150°. Unstable in light, air, alkaline conditions. d2020 1.010; nD20 1.5040; nD30 1.5023. Practically insol in water. Sol in alcohol, petr ether, kerosene, carbon tetrachloride, ethylene dichloride, nitromethane. Incompatible with alkalies.
Boiling point: bp 0.1 140°
Index of refraction: nD20 1.5040; nD30 1.5023
Density: d2020 1.010
 
Derivative Type: Allethrin II
CAS Registry Number: 497-92-7
Additional Names: 3-(3-Methoxy-2-methyl-3-oxo-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl ester; allethrolone ester of chrysanthemumdicarboxylic acid monomethyl ester
Manufacturers' Codes: ENT-17510
Molecular Formula: C20H26O5
Molecular Weight: 346.42
Percent Composition: C 69.34%, H 7.56%, O 23.09%
Literature References: Synthesis: M. Matsui, Y. Yamada, Agric. Biol. Chem. 27, 373 (1963); M. Matsui, H. Meguro, ibid. 28, 27 (1964); M. Elliott, N. F. Janes, Chem. Ind. (London) 1969, 270; A. Kobayashi et al., Agric. Biol. Chem. 35, 1961 (1971); T. Sugiyama et al., ibid. 36, 565 (1972).
Properties: Oily pale yellow liq. nD20.6 1.5156. uv max (ethanol): 232 nm (e 23000). Unstable in light, air, alkaline conditions. Sol in organic solvents. Practically insol in water.
Index of refraction: nD20.6 1.5156
Absorption maximum: uv max (ethanol): 232 nm (e 23000)
 
CAUTION: Potential symptoms of toxicity are similar to those of the pyrethrins.
Use: Insecticide.

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