5983. Methoprene

Nomenclature

CAS number: 40596-69-8
(2E,4E)-11-Methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid 1-methylethyl ester; isopropyl (2E,4E,7RS)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate; ZR-515.
C19H34O3; mol wt 310.47.
C 73.50%, H 11.04%, O 15.46%.

Description and references

Juvenile hormone mimic. Prepn: BE 778242; see also C. A. Henrick, US 3818047 (1972, 1974 both to Zoecon); idem et al., J. Org. Chem. 40, 1 (1975); L. Novák et al., Ann. 1982, 1173. Effect on mustard aphid: P. J. Rup, R. K. Gill, Insect Sci. Applic. 14, 173 (1993). Field trial in a saltwater marsh against mosquitoes: V. L. Kramer et al., J. Am. Mosq. Control Assoc. 9, 127 (1993). Mechanism of action study: E. M. Berger et al., Dev. Biol. 151, 410 (1992). HPLC determn in tobacco: S. S. Yang, Chromatographia 33, 309 (1992). GC determn in aquatic microcosms: D. H. Ross et al., J. Am. Mosq. Control Assoc. 10, 202 (1994). Impact on the fathead minnow: idem et al., ibid. 211. Review of properties, metabolism, toxicology, and use: J. B. Siddall, Environ. Health Perspect. 14, 119-126 (1976). Review of analytical methods: L. L. Dunham, W. W. Miller in Analytical Methods for Pesticides and Plant Growth Regulators vol. X, G. Zweig, Ed. (Academic Press, New York, 1978) pp 95-109.

Chemical structure

Properties

Amber liquid, bp0.06 135-136°. d20 0.9261 g/ml. Vapor pressure at 25°: 2.37 × 105 mm Hg. Soly in water at 25°: 1.39 ppm. Sol in org solvents. Temperature stable up to at least 42° for 24 months. Stable in water, org solvents, and in the presence of dil alkali and acid. LD50 orally in rats: >34500 mg/kg (Siddall).

Derivative

(7S)-Form.

Nomenclature

CAS number: 65733-16-6
S-Methoprene; ZR-2458; Altosid (Wellmark); Precor (Wellmark); Extinguish (Wellmark); Pharorid (Wellmark).

Use

Insecticide; insect growth regulator.

Therapeutic Category (Veterinary)

Ectoparasiticide.