5570. Looplure

Nomenclature

CAS number: 14959-86-5
(Z)-7-Dodecen-1-ol acetate; cis-7-dodecenyl acetate; cis-1-acetoxy-7-dodecene; ENT-33266.
C14H26O2; mol wt 226.36.
C 74.28%, H 11.58%, O 14.14%.

Description and references

Sex pheromone of the female cabbage looper moth, Trichoplusia ni (Hübner). Isoln, identification and synthesis: R. S. Berger, Ann. Entomol. Soc. Am. 59, 767 (1966). Synthesis and activity of isomers: N. Green et al., J. Med. Chem. 10, 533 (1967); H. H. Toba et al., J. Econ. Entomol. 63, 1048 (1970). Alternate syntheses: W. Seidel et al., Ber. 110, 3544 (1977); H. J. Bestmann et al., Ber. 112, 1923 (1979); M. Horiike, C. Hirano, Agric. Biol. Chem. 44, 2229 (1980); D. Basavaiah et al., J. Org. Chem. 47, 1792 (1982). Acute toxicity study: M. Beroza et al., Toxicol. Appl. Pharmacol. 31, 421 (1975).

Chemical structure

Properties

Oil, bp0.05 98-100°. nD25 1.4420. LD50 in rats (mg/kg): >13430 orally; in rabbits (mg/kg): >2025 dermally; LC50 (24 hr) in rainbow trout, bluegill sunfish (ppm): >100, >100 (Beroza).

Use

Insect attractant.