260. Allethrins

Nomenclature

Allyl cinerins.

Description and references

Synthetic analogues 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.

Chemical structure

Derivative

Allethrin I.

Nomenclature

CAS number: 584-79-2
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; Pynamin (Sumitomo).
C19H26O3; mol wt 302.41.
C 75.46%, H 8.67%, O 15.87%.

Description and 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. Poisonous. 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.

Derivative

Allethrin II.

Nomenclature

CAS number: 497-92-7
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; ENT-17510.
C20H26O5; mol wt 346.42.
C 69.34%, H 7.56%, O 23.09%.

Description and 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. Poisonous. nD20.6 1.5156. uv max (ethanol): 232 nm (ε 23000). Unstable in light, air, alkaline conditions. Sol in organic solvents. Practically insol in water.

Caution

Potential symptoms of toxicity are similar to those of the pyrethrins.

Use

Insecticide.