2381. Clomazone

Nomenclature

CAS number: 81777-89-1
2-[(2-Chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone; dimethazone; FMC-57020; Command (FMC).
C12H14ClNO2; mol wt 239.70.
C 60.13%, H 5.89%, Cl 14.79%, N 5.84%, O 13.35%.

Description and references

Pre-emergence herbicide; inhibits biosynthesis of photosynthetic pigments in susceptible species. Prepn: J. H. Chang, BE 889040; idem, US 4405357 (1982, 1983 both to FMC). Use on soybeans: M. P. Mascianica, Proc. Annu. Meet. Northeast. Weed Sci. Soc. 39, 25 (1985); on white potatoes: C. C. Kupatt et al., ibid. 166. Fate in soil: T. L. Mervosh et al., J. Agric. Food Chem. 43, 537 (1995). Review of properties and analytical methods: A. W. Chen in Comprehensive Analytical Profiles of Important Pesticides, J. Sherma, T. Cairns, Eds. (CRC Press, Boca Raton, 1993) pp 131-148.

Chemical structure

Properties

Light brown viscous liquid, mp 25°. Vapor pressure at 25°: 1.4 × 10-6 mm Hg. d20 1.19. Soly in water: 1100 ppm. Readily sol in chloroform, methanol, methylene chloride, heptane, acetonitrile, toluene, acetone, dioxane, xylene, hexane. LD50 in male rats, female rats, mallard duck-bobwhite quail (mg/kg): 2077, 1369, >2510 orally; in rabbits (mg/kg): >2000 dermally (Chen).

Use

Herbicide.