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Diflufenican 50%SC

Herbicide
HRAC F1 WSSA 12; pyridinecarboxamide

NOMENCLATURE
Common name diflufenican (BSI, draft E-ISO, (m) draft F-ISO); diflufenicanil ((m) France)
IUPAC name 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide
Chemical Abstracts name N-(2,4-difluorophenyl)-2-[3-(trifluoromethyl)phenoxy]-3-pyridinecarboxamide
Other names DFF CAS RN [83164-33-4] Development codes M&B 38 544 (May & Baker)

Diflufenican APPLICATIONS
Biochemistry Blocks carotenoid biosynthesis, by inhibition of phytoene desaturase. Mode of action Selective contact and residual herbicide, absorbed principally by the shoots of germinating seedlings, with limited translocation. Uses Applied at 125-250 g/ha pre- or early post-emergence in autumn-sown wheat and barley, to control grass and broad-leaved weeds, particularly Galium, Veronica and Viola spp. Normally used in combination with isoproturon or other cereal herbicides. Phytotoxicity Any slight phytotoxicity is in the form of small transient patches on basal leaves, with no adverse effect on crop development. Formulation types SC; WP. Selected tradenames: 'Fenican' (Aventis); 'Tigrex' (Aventis); mixtures: 'Bacara' (+ flurtamone) (Aventis); 'Javelin' (+ isoproturon) (Aventis)

Diflufenican OTHER TRADENAMES
'Blizzard' (Aventis); 'Brodal' (Aventis); 'Econal' (Aventis); 'Ioniz' (Aventis); 'Zodiac TX' (Aventis) mixtures: 'Ardent' (+ trifluralin) (Aventis); 'Azur' (+ ioxynil+ isoproturon) (Aventis); 'Capture' (+ bromoxynil+ ioxynil) (Aventis); 'Carat' (+ flurtamone) (Aventis); 'Cougar' (+ isoproturon) (Aventis);' (+ bromoxynil+ mecoprop-P) (Aventis); 'Fenikan' (+ isoproturon) (Aventis); 'Grenadier' (+ isoproturon) (Aventis); 'Ingot' (+ flurtamone+ isoproturon) (Aventis); 'Javelin Gold' (+ isoproturon) (Aventis); 'Lucifer' (+ clodinafop-propargyl) (Aventis); 'Panther' (+ isoproturon) (Aventis); 'Quartz' (+ isoproturon) (Aventis); 'Tolkan Turbo' (+ isoproturon) (Aventis); 'Traviata' (+ bromoxynil+ mecoprop-P) (Aventis); 'Amazon' (+ clodinafop-propargyl) (Syngenta); 'First' (+ bromoxynil+ ioxynil) (Aventis, Philagro); 'Galace' (+ trifluralin) (Dow AgroSciences); 'Halbard' (+ cyanazine) (BASF); 'Herold' (+ flufenacet) (Bayer); 'Landgold DFF 625' (+ isoproturon) (Landgold) Discontinued names mixtures: 'Bolero' * (+ terbuthylazine) (Novartis)

Diflufenican ANALYSIS
Methods have been developed to determine residues in plants and soil (J. Agric. Food Chem. 1991, 39(5), 968-76).

MAMMALIAN TOXICOLOGY
Reviews Proc. Br. Crop Prot. Conf. - Weeds, 1985, 1, 23-28. Oral Acute oral LD50 for rats >2000, mice >1000, rabbits >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 (4 h) for rats >2.34 mg/l air. NOEL In 14 d sub-acute trials in rats, no adverse effect observed at 1600 mg/kg b.w. In 90 d feeding trials, NOEL for dogs was 1000 mg/kg b.w. daily, for rats 500 ppm diet. Other Non-mutagenic in the Ames test. Toxicity class WHO (a.i.) III (Table 5) EC hazard R52, R53

Diflufenican ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2150, mallard ducks >4000 mg/kg. Fish LC50 (96 h) for rainbow trout 56-100, carp 105 mg/l. Daphnia LC50 (48 h) - no effect at 10 mg/l. Algae No growth inhibition of algae (96 h) at 10 mg/l. Bees Non-toxic by ingestion or contact. Worms Non-toxic to earthworms.

ENVIRONMENTAL FATE
Plants In cereals, rapidly metabolised via the nicotinamide and nicotinic acid to CO2. Following pre-emergence application in autumn, no residues are detectable in the grain and straw after c. 200-250 days. Soil/Environment In soil, degradation proceeds via the metabolites 2-(3-trifluoromethylphenoxy)nicotinamide and 2-(3-trifluoromethylphenoxy)nicotinic acid to bound residues and CO2. Half-life varies from 15 to 30 weeks, depending on soil type and water content.