trifloxystrobin (788)
Fungicide
FRAC 11; strobilurin type: oximinoacetate
NOMENCLATURE
Common name trifloxystrobin (BSI, pa ISO)
IUPAC name methyl (E)-methoxyimino-{(E)-a-[1-(a,a,a-trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetate
Chemical Abstracts name methyl (E,E)-a-(methoxyimino)-2-[[[[1-[3-(trifluoromethyl)phenyl]ethylidine]amino]oxy]methyl]benzeneacetate
CAS RN [141517-21-7] Development codes CGA 279202 (Novartis)
PHYSICAL CHEMISTRY
Mol. wt. 408.4 M.f. C20H19F3N2O4 Form Odourless, white solid. M.p. 72.9 癈 B.p. c. 312 癈 (decomp. starts at 285 癈) V.p. 3.4 ?10-3 mPa (25 癈) KOW logP = 4.5 (25 癈) Henry 2.3 ?10-3 Pa m3 mol-1 (25 癈) Solubility In water 610 mg/l (25 癈). Stability Hydrolysis DT50 11.4 w (pH 7); stable at pH 5. Aqueous photolysis DT50 31.5 h (pH 7, 25 癈).
COMMERCIALISATION
History Reported by P. Margot et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 375). Introduced by Novartis AG (became Syngenta AG) in Switzerland, South Africa and USA in 1999. All rights sold to Bayer AG in 2000. Patents EP-A-460575 Manufacturers Bayer
APPLICATIONS
Biochemistry Inhibits mitochondrial respiration by blocking electron transfer at the Qo centre of cytochrome bc1. Mode of action Mesostemic, broad-spectrum fungicide with preventative and specific curative activity and displaying rain-fastness. Redistributed by superficial vapour movement and also has translaminar activity. Uses Controls a range of cereal diseases, including powdery mildews, leaf spots and rusts (at 100-187 g/ha). Also effective against leaf spots, powdery mildews, bunch and fruit rots of pome fruit, grapes, peanuts, bananas and vegetables (at 50-140 g/ha). Formulation types EC; WG. Selected tradenames: 'Flint' (Bayer); 'Tega' (Bayer); mixtures: 'Stratego' (+ propiconazole) (Bayer)
OTHER TRADENAMES
'Compass' (Bayer); 'Twist' (Bayer) mixtures: 'Agora' (+ cyproconazole) (Bayer); 'Eclair' (+ cymoxanil) (Bayer)
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits); may cause sensitisation by skin contact. Inhalation LC50 for rats >4646 mg/m3. ADI 0.05 mg/kg. Other Non-mutagenic, non-teratogenic, non-carcinogenic; no adverse effects on reproduction. Toxicity class WHO (a.i.) III
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Fish LC50 (96 h) for rainbow trout 0.015 mg/l. Daphnia LC50 (48 h) 0.016 mg/l. Other aquatic spp. Toxic to aquatic organisms in laboratory tests. Considered low risk to aquatic ecosystems when used as recommended, due to low use rates and rapid dissipation in biotic environments. Bees LD50 (oral) >200 mg/bee. Worms LC50 (14 d) >1000 mg/kg soil. Other beneficial spp. Harmless in normal use to a wide range of beneficial arthropods, including predatory mites, ground- and foliage- dwelling predators and parasitic wasps.
ENVIRONMENTAL FATE
Animals In rats, absorbed from the gastrointestinal tract, rapidly metabolised and quickly and completely eliminated from the body. Plants Rapidly degraded; metabolic profile is similar for a range of crops, with the parent and the acid metabolite being the relevant compounds for residues determination. Soil/Environment Dissipates rapidly from soil and surface water. Soil DT50 4.2-9.5 d. Koc 1642-3745. No leaching potential. In water, DT50 0.3-1 d, DT90 4-8 d. |
