3199. Dikegulac

Nomenclature

CAS number: 18467-77-1
2,3:4,6-Bis-O-(methylethylidene)-α-l-xylo-2-hexulofuranosonic acid; α-2,3:4,6-di-O-isopropylidene-l-xylo-hexulofuranosonic acid; di-O-isopropylidene-2-keto-l-gulonic acid; diacetone-2-ketogulonic acid; diacetone-2-oxo-l-gulonic acid; oxogulonic acid diacetonide.
C12H18O7; mol wt 274.27.
C 52.55%, H 6.61%, O 40.83%.

Description and references

Intermediate in the manuf of ascorbic acid, q.v. Manufacturing process: G. M. Jaffe, E. J. Pleven, DE 2123621; eidem, US 3832355 (1970, 1974 both to Hoffmann-La Roche). Use as a plant growth regulator: W. Szkrybalo, DE 2339239; eidem, US 4337080 (1974, 1982 both to Hoffmann-La Roche); P. Bocian et al., Nature 258, 142 (1975). Physicochemical properties, toxicity and growth retardant effect: W. H. de Silva et al., Proc. Br. Crop Prot. Conf. - Weeds 1976, 349. Activity: S. S. Purohit, Comp. Physiol. Ecol. 4, 264 (1979); 6, 261 (1981).

Chemical structure

Derivative

Sodium salt.

Nomenclature

Dikegulac-sodium; Ro-7-6145; Atrinal (Roche).
C12H17NaO7; mol wt 296.25.
C 48.65%, H 5.78%, Na 7.76%, O 37.80%.

Properties

Powder, mp >300°. Vapor pressure at 25°: <10-10 mm Hg. Soly at 20° (g/l): water 590; methanol 390; ethanol 230; chloroform 60; acetone <10; hexane <10; cyclohexanone <10. LD50 in mice, male, female rats (mg/kg): 19500, 31000, 18000 orally; LC50 (96 hr) in bluegill sunfish, rainbow trout (ppm): >10000, >5000 (de Silva).

Use

Plant growth regulator; herbicide.