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Oxyfluorfen

Oxyfluorfen 95%TC
Oxyfluorfen 24%EC

Herbicide
HRAC E WSSA 14; diphenyl ether

Oxyfluorfen NOMENCLATURE
Common name oxyfluorfen (BSI, E-ISO, ANSI, WSSA); oxyfluorfène ((m) F-ISO)
IUPAC name 2-chloro-,,-trifluoro-p-tolyl 3-ethoxy-4-nitrophenyl ether
Chemical Abstracts name 2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4-(trifluoromethyl)benzene
CAS RN [42874-03-3] EEC no. 255-983-0 Development codes RH-2915 (Rohm & Haas)

Oxyfluorfen PHYSICAL CHEMISTRY
Mol. wt. 361.7 M.f. C15H11ClF3NO4 Form Orange, crystalline solid. M.p. 85-90 ºC; (tech., 65-84 ºC) B.p. 358.2 ºC (decomp.) V.p. (pure a.i.) 0.0267 mPa (25 ºC) KOW logP = 4.47 S.g./density 1.35 (73 ºC) Solubility In water 0.116 mg/l (25 ºC). Readily soluble in most organic solvents, e.g. acetone 72.5, cyclohexanone, isophorone 61.5, dimethylformamide >50, chloroform 50-55, mesityl oxide 40-50 (all in g/100 g, 25 ºC). Stability No significant hydrolysis in 28 d at pH 5-9 (25 ºC). Decomposed rapidly by u.v. irradiation; DT50 3 d (room temperature). Stable up to 50 ºC.

Oxyfluorfen COMMERCIALISATION
History Herbicide reported by R. Y. Yih & C. Swithenbank (J. Agric. Food Chem., 1975, 23, 592). Introduced by Rohm & Haas Co. (now Dow AgroSciences) and first marketed in 1976. Patents US 3798276 Manufacturers Dow AgroSciences; Makhteshim-Agan; Sannong

Oxyfluorfen APPLICATIONS
Biochemistry Protoporphyrinogen oxidase inhibitor. Mode of action Selective contact herbicide, absorbed more readily by the foliage (and especially the shoots) than by the roots, with very little translocation. Uses Control of annual broad-leaved weeds and grasses in a variety of tropical and subtropical crops, by pre- or post-emergence application at rates in the range 0.25-2.0 kg/ha. Particular crops include tree fruit (including citrus), vines, nuts, cereals, maize, soya beans, peanuts, rice, cotton, bananas, peppermint, onions, garlic, ornamental trees and shrubs, and conifer seedbeds. Phytotoxicity Soya beans and cotton may be injured by contact with oxyfluorfen. Formulation types EC; GR. Selected products: 'Goal' (Dow AgroSciences); 'Galigan' (Makhteshim-Agan); 'Hadaf' (Vapco)