4805. Hydroprene

Nomenclature

CAS number: 41096-46-2
(2E,4E)-3,7,11-Trimethyl-2,4-dodecadienoic acid ethyl ester; ethyl (2E,4E)-3,7,11-trimethyldodeca-2,4-dienoate; OMS-1696; SHA-486300; ZR-512; Gencor (Zoecon); Gentrol (Wellmark).
C17H30O2; mol wt 266.42.
C 76.64%, H 11.35%, O 12.01%.

Description and references

Juvenile hormone mimic. Prepn: C. A. Henrick, US 4021461 (1977 to Zoecon); idem et al., J. Agric. Food Chem. 21, 354 (1973); and insecticidal activity of enantiomers: idem et al., ibid. 26, 542 (1978). Effect on sweet potato weevil: G. M. Ram, A. C. Sekhar, Indian J. Comp. Anim. Physiol. 2, 87 (1991); cockroach: B. L. Reid, G. W. Bennett, J. Econ. Entomol. 87, 1537 (1994). Effect of (S)-enantiomer on cockroach: J. P. Edwards, J. E. Short, ibid. 86, 436 (1993). Review and use in food industries: M. Martinez, Cereal Foods World 38, 818-820 (1993).

Chemical structure

Properties

bp0.03 95°. uv max (hexane): 262 nm (ε 28300). LD50 orally in rats: >34000 mg/kg (Edwards).

Derivative

(S)-form.

Nomenclature

CAS number: 65733-18-8

Properties

bp0.05 80°. [α]D25 +2.9° (c = 0.020 in methanol).

Use

Insect growth regulator; insecticide.