Herbicide

HRAC  E WSSA  14; diphenyl ether

NOMENCLATURE

fluoroglycofen-ethyl

Common name fluoroglycofen-ethyl

CAS RN [77501-90-7]  Development codes RH-0265 (Rohm & Haas) 

fluoroglycofen

Common name fluoroglycofen (BSI, ANSI, draft E-ISO); fluoroglycofène ((m) draft F-ISO)

IUPAC name O-[5-(2-chloro-a,a,a-trifluoro-p-tolyloxy)-2-nitrobenzoyl]glycolic acid 

Chemical Abstracts name carboxymethyl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate 

CAS RN [77501-60-1] 

PHYSICAL CHEMISTRY

fluoroglycofen-ethyl

Mol. wt. 447.8  M.f. C18H13ClF3NO7  Form Dark amber solid.  M.p. 65 ºC  KOW logP = 3.65  S.g./density 1.01 (25 ºC)  Solubility In water 0.6 mg/l (25 ºC). Readily soluble in most organic solvents (except hexane).  Stability In aqueous solution, 0.25 mg/l, at 22 ºC, DT50 c. 231 d (pH 5), 15 d (pH 7), 0.15 d (pH 9); aqueous suspensions are rapidly decomposed by u.v. light. 

fluoroglycofen

Mol. wt. 419.7  M.f. C16H9ClF3NO7 

COMMERCIALISATION

History Herbicide developed by Rohm & Haas Co. as the ethyl ester.  Manufacturers Rohm & Haas

APPLICATIONS

fluoroglycofen-ethyl

Biochemistry Protoporphyrinogen oxidase inhibitor.  Mode of action Fluoroglycofen-ethyl is a selective leaf- and root- herbicide.  Uses Post-emergence control of broad-leaved weeds and grasses (particularly Galium, Viola, and Veronica spp.) in wheat, barley, oats, peanuts, rice, and soya beans.  Formulation types EC; WP.  Compatibility Incompatible with suspension concentrate formulations.  Selected tradenames: 'Compete' (Rohm & Haas); mixtures: 'Satis' (+ triasulfuron) (Syngenta)

OTHER TRADENAMES

fluoroglycofen-ethyl

Mixtures: 'BAS 56802H' (+ dichlorprop-P) (BASF); 'Competitor' (+ isoproturon) (Aventis); 'Kuorum' (+ isoproturon) (Aventis); 'Presto' (+ metosulam) (Dow AgroSciences) Discontinued names mixtures: 'Stefes Competitor' * (+ isoproturon) (Stefes)

ANALYSIS

Product by gc. Residues by glc with halogen-specific MCD. Details from Rohm & Haas. 

MAMMALIAN TOXICOLOGY

fluoroglycofen-ethyl

Reviews UK MAFF Scientific Sub-committee on Pesticides, Disclosure Document for Fluoroglycofen-ethyl, Feb. 1992.  Oral Acute oral LD50 for rats 1500 mg/kg.  Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg; slight irritant to their skin and eyes.  Inhalation LC50 (4 h) for rats >7.5 mg EC formulation/l.  NOEL (1 y) for dogs 320 mg/kg diet.  ADI 0.009 mg/kg.  Other Non-mutagenic in the Ames test.  Toxicity class WHO (a.i.) III 

ECOTOXICOLOGY

fluoroglycofen-ethyl

Birds Acute oral LD50 for bobwhite quail >3160 mg/kg. Dietary LC50 (8 d) for mallard ducks and bobwhite quail >5000 mg a.i./kg.  Fish LC50 (96 h) for bluegill sunfish 1.6, trout 23 mg/l.  Daphnia LC50 (48 h) 30 mg/l.  Bees LD50 (contact) >100 mg/bee. 

ENVIRONMENTAL FATE