3361. Disparlure

Nomenclature

CAS number: 29804-22-6 (cis-form); 54910-51-9 (2S-cis-form)
(2S-cis)-2-Decyl-3-(5-methylhexyl)oxirane; cis-7,8-epoxy-2-methyloctadecane; ENT-34886; Disrupt (Hercon).
C19H38O; mol wt 282.50.
C 80.78%, H 13.56%, O 5.66%.

Description and references

Potent sex pheromone of the gypsy moth Lymantria dispar (formerly Porthetria dispar). Isoln and characterization: B. A. Bierl et al., Science 170, 87 (1970); eidem, J. Econ. Entomol. 65, 659 (1972). Synthesis: S. Iwaki et al., J. Am. Chem. Soc. 96, 7842 (1974); D. G. Farnum et al., Tetrahedron Lett. 1977, 4009; K. Mori et al., Tetrahedron 35, 833 (1979); B. E. Rossiter et al., J. Am. Chem. Soc. 103, 464 (1981); K. Mori, T. Ebata, Tetrahedron Lett. 22, 4281 (1981). Synthesis of (±)-form: K. Eiter, Angew. Chem. Int. Ed. 11, 60 (1972); idem, DE 2145454; idem, US 3975409 (1973, 1976 both to Bayer); H. J. Bestmann et al., Ber. 109, 3375 (1976). Activity of (+)- and (±)-forms: R. T. Cardé, R. P. Webster, J. Chem. Ecol. 5, 935 (1979). Acute toxicity study: M. Beroza et al., Toxicol. Appl. Pharmacol. 31, 421 (1975).

Chemical structure

Properties

Viscous colorless oil, bp0.25 146-148°. [α]D23 +0.8 ±0.2° (c = 10 in CCl4). nD23 1.4450. LD50 in rats (mg/kg): >34600 orally; in rabbits (mg/kg): >2025 dermally; LC50 (24 hr) in rainbow trout, bluegill sunfish (ppm): >100, >100 (Beroza).

Use

Insect attractant.