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trifloxystrobin
Fungicide
FRAC 11, C3; 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 (aE)-a-(methoxyimino)-2-[[[(E)-[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methyl]benzeneacetate
CAS RN [141517-21-7]; [221007-60-9] former number Development codes CGA 279202
PHYSICAL CHEMISTRY
Mol. wt. 408.4 M.f. C20H19F3N2O4 Form Odourless, white solid. M.p. 72.9 °C B.p. c. 312 °C (decomp. starts at 285 °C) V.p. 3.4 ´ 10-3 mPa (25 °C) KOW logP = 4.5 (25 °C) Henry 2.3 ´ 10-3 Pa m3 mol-1 (25 °C) S.g./density 1.36 (21 °C) Solubility In water 610 mg/l (25 °C). Stability Hydrolysis DT50 11.4 w (pH 7); stable at pH 5. Aqueous photolysis DT50 31.5 h (pH 7, 25 °C).
COMMERCIALISATION
History Reported by P. Margot et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 375). Introduced by Novartis Crop Protection AG (became Syngenta AG) in Switzerland, South Africa and USA in 1999. All rights sold to Bayer AG in 2000. Patents EP 00460575 Manufacturers Bayer CropScience
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 Broad spectrum fungicide for foliar use on a wide range of agricultural and horticultural crops in temperate, sub-tropical and tropical climates in open fields or protected under glass and plastic. In Europe its uses will be focussed on cereals (at 50 g/ha), grapes (at 187.5 g/ha), pome fruit (at 75 g/ha), and cucurbit crops (at 187.5 g/ha).Trifloxystrobin is active against fungi in all four classes - Ascomycetes, Deuteromycetes, Basidiomycetes and Oomycetes. Formulation types EC; SC; WG. Selected products: 'Flint' (Bayer CropScience); 'Tega' (Bayer CropScience); mixtures: 'Stratego' (+ propiconazole) (Bayer CropScience)
OTHER PRODUCTS
'Buy' (Me2); 'Compass' (Bayer CropScience); 'Gem' (Bayer CropScience); 'Twist' (Bayer CropScience); 'Zatao' (Bayer CropScience) mixtures: 'Eclair' (+ cymoxanil) (Bayer CropScience); 'Rombus' (+ propiconazole) (Bayer CropScience); 'Sphere' (+ cyproconazole) (Bayer CropScience) Discontinued products mixtures: 'Agora' * (+ cyproconazole) (Bayer)
MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Classified as non-irritating to skin and eyes (rabbits); may cause sensitisation by skin contact. Inhalation LC50 for rats >4646 mg/m3. NOEL NOAEL (2 y) for rats 9.8 mg/kg b.w. daily. ADI 0.1 mg/kg (company proposed) Other Non-mutagenic, non-teratogenic, non-carcinogenic; no adverse effects on reproduction. Toxicity class WHO (a.i.) III (company classification)
ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail >2000, for mallard ducks >2250 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5050 ppm. Fish LC50 (96 h) for rainbow trout 0.015, bluegill sunfish 0.054 mg/l. Daphnia LC50 (48 h) 0.016 mg/l. Algae EbC50 for Scenedesmus subspicatus 0.0053 mg/l. Other aquatic spp. Toxic to aquatic organisms in laboratory tests but rapid dissipation in biotic environments. Low risk to aquatic ecosystems has been demonstrated in outdoor mesocosm tests. Bees LD50 (oral) >200 mg/bee. Worms LC50 (14 d) >1000 mg/kg soil. Other beneficial spp. Low risk 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 Metabolic profile is similar for a range of crops. Based on wheat, apple, cucumber and sugar beet metabolism data, trifloxystrobin is considered as the residue of concern for food and feed commodities of plant origin. 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.
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