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Clomazone

Clomazone 95%TC
Clomazone 48%EC

Herbicide
HRAC F3 WSSA 13; isoxazolidinone

Clomazone NOMENCLATURE
Common name clomazone (BSI, ANSI, draft E-ISO, (f) draft F-ISO)
IUPAC name 2-(2-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one; 2-(2-chlorobenzyl)-4,4-dimethylisoxazolidin-3-one
Chemical Abstracts name 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3-isoxazolidinone
Other names dimethazone* CAS RN [81777-89-1] Development codes FMC 57 020

Clomazone PHYSICAL CHEMISTRY
Mol. wt. 239.7 M.f. C12H14ClNO2 Form Clear, colourless to light brown, viscous liquid. M.p. 25 ºC B.p. 275 ºC V.p. 19.2 mPa (25 ºC) KOW logP = 2.5 Henry 4.19  10-3 Pa m3 mol-1 S.g./density 1.192 (20 ºC) Solubility In water 1.1 g/l. Miscible with acetone, acetonitrile, chloroform, cyclohexanone, dichloromethane, methanol, toluene, heptane, dimethylformamide. Stability Stable at ambient temperatures for at least 2 y; stable at 50 ºC for at least 3 mo. In sunlight, DT50 >30 d in aqueous solution. F.p. 70-75 ºC (closed cup)

COMMERCIALISATION
History Herbicide introduced by FMC Corp. Patents US 4405357 Manufacturers FMC; Sannong

Clomazone APPLICATIONS
Biochemistry Inhibits carotenoid biosynthesis; target enzyme not known. Mode of action Selective herbicide, absorbed by the roots and shoots and translocated upward. Susceptible species emerge but are devoid of pigmentation. Uses Control of broad-leaved and grass weeds in soya beans, peas, maize, oilseed rape, sugar cane, cassava, pumpkins, and tobacco. Applied pre-emergence or pre-plant incorporated. Phytotoxicity Foliar contact or vapours may cause visual symptoms of chlorosis to nearby sensitive plants. Formulation types CS; EC; WP. Compatibility Compatible with many other herbicides, e.g. metribuzin, linuron, chloramben, alachlor, trifluralin, pendimethalin, metolachlor, oryzalin or ethalfluralin. Selected products: 'Command' (FMC); 'Kalif' (Makhteshim-Agan); mixtures: 'Commence' (+ trifluralin) (FMC); 'Brasan' (+ dimethachlor) (Syngenta)