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Fungicides

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Fosetyl Al

FRAC 33, U phosphonate

NOMENCLATURE
fosetyl-aluminium
Common name fosetyl-aluminium IUPAC namealuminiumtris-O-ethylphosphonate
Other names efosite-Al* (rejected common name proposal); EPAL CAS RN [39148–24–8] EC no. 254–320–2 Development codes LS 74 783; RP 32545 (both Rhône-Poulenc) Smiles code CCOP(=O)O[Al](OP(=O)OCC)OP(=O)OCC
fosetyl
Common name fosétyl ((m) F-ISO); fosetyl (BSI, E-ISO); phosethyl* ((m) draft F-ISO (before 1984)) IUPAC name ethyl hydrogen phosphonate
Chemical Abstracts name ethyl hydrogen phosphonate Other names efosite* (rejected common name proposal) CAS RN [15845–66–6]
PHYSICAL CHEMISTRY
Composition Tech. is ≥96% pure. Mol. wt. 354.1 M.f. C6H18AlO9P3 Form Colourless powder; (tech. is a white to yellowish powder). M.p. 215 °C Kow logP = –2.1 to –2.7 (23 °C) S.g./density 1.529 (99.1%), 1.54 (97.6%) (both 20 °C) Solubility In water 111.3 g/l (pH 6, 20 °C). In methanol 807, acetone 6, ethyl acetate <1 (all in mg/l, 20 °C).Stability Hydrolysis of fosetyl-aluminium occurs under extreme acid or alkaline conditions. DT50 5 d (pH 3), 13.4 d (pH 13).Decomposes above 276 °C.Photostability DT50 23 daylight hours.pKa 4.7 (20 °C)
fosetyl
Mol. wt. 110.0 M.f. C2H7O3P
COMMERCIALISATION
History Fungicidal activity of aluminium salt reported by D. Horrièreet al. (Phytiatr.-Phytopharm., 1977, 26, 3). Fosetyl-aluminium was introduced by Rhône-Poulenc Agrochimie (now Bayer AG); first registered in 1977 in France. Patents FR 2254276 Manufacturers Cheminova; Dacheng; Isochem; Jiahua; Lanxi; Limin; Tide
APPLICATIONS
fosetyl-aluminium
Biochemistry Possibly acts by inhibiting germination of spores or by blocking development of mycelium and sporulation. Mode of action Systemic fungicide, rapidly absorbed through the plant leaves or roots, with translocation both acropetally and basipetally. Uses Control of diseases caused by e.g. Phytophthora, Pythium, Plasmopara, Bremia spp., etc. on a variety of crops, including vines, fruit (citrus, pineapples, avocados, stone fruit and pome fruit), berries, vegetables, hops, ornamentals and turf. Application rates range from 1–7 kg/ha in citrus, 2 kg/ha in tree nuts, up to 3.6 kg/ha in pome fruit, 2 kg/ha in grapes, and 2.4–4.5 kg/ha in cucumbers. Also useful activity against several bacterial plant pathogens.Formulation types WG; WP. Compatibility Incompatible with foliar fertilisers.
PRODUCTS
fosetyl-aluminium
Selected products ‘Aliette’ (Bayer CropScience) ; ‘Fitonette’ (Baocheng) ; ‘Fosim’ (Agrimix) ; ‘Fostar’ (Mobedco) ; ‘Manaus’ (Rocca) ; ‘Valete’ (Vapco) ; ‘Vialphos’ (Vipesco) mixtures ‘Mikal’ (various mixtures) (+ folpet) (Bayer CropScience, Bayer CropScience) ; ‘Profiler’ (+ fluopicolide) (Bayer CropScience, Bayer CropScience) ; ‘Verita’ (+ fenamidone) (Bayer CropScience, Bayer CropScience) Other products ‘Alfil’ (Afrasa) ; ‘Alfosetil’ (Hektaş) ; ‘Alliagro’ (Agropharm) ; ‘Avi’ (Herbos) ; ‘Chipco Signature’ (Bayer CropScience) ; ‘Contender’ (Chimiberg) ; ‘Epal’ (Agrimport) ; ‘Etylit’ (Sapec) ; ‘Fesil’ (IQV Italia) ; ‘Flanker’ (Novasource) ; ‘Fosbel’ (Probelte) ; ‘Fosetal’ (Papaeconomou) ; ‘Kelly’ (Siapa) ; ‘Linebacker’ (Novasource) ; ‘Pilarfarm’ (Pilarquim) ; ‘Plant Care’ (Doğal) mixtures ‘Alfil Duplo’ (+ mancozeb) (Afrasa, Afrasa) ; ‘Altigan Flash’ (+ folpet) (Bayer CropScience, Bayer CropScience) ; ‘Artimon’ (+ mancozeb) (Philagro, Philagro) ; ‘Attila’ (+ folpet) (Herbos, Herbos) ; ‘Chipco Green’ (+ iprodione) (Bayer Environmental Science, Bayer Environmental Science) ; ‘Elicio’ (+ fenamidone + fenamidone) (Bayer CropScience, Bayer CropScience, Sipcam S.p.A., Sipcam S.p.A.) ; ‘Equation System’ (+ famoxadone) (DuPont, DuPont) ; ‘FosimCombi’ (+ folpet) (Agrimix, Agrimix) ; ‘FosimTriplo’ (+ mancozeb + folpet) (Agrimix, Agrimix, Agrimix) ; ‘Impresario’ (+ famoxadone) (DuPont, DuPont) ; ‘Input N’ (+ benalaxyl + mancozeb) (Siapa, Siapa, Siapa) ; ‘Keeper Effe’ (+ folpet) (Chimiberg, Chimiberg) ; ‘Keeper Erre’ (+ copper oxychloride) (Chimiberg, Chimiberg) ; ‘Keeper Triplo’ (+ cymoxanil + mancozeb) (Chimiberg, Chimiberg, Chimiberg) ; ‘Kelly R’ (+ copper oxychloride) (Siapa, Siapa) ; ‘Maestro F’ (+ folpet) (Sapec, Sapec) ; ‘Maestro M’ (+ mancozeb) (Sapec, Sapec) ; ‘Magma Triple’ (+ cymoxanil + folpet) (Afrasa, Afrasa, Afrasa) ; ‘Melody Trio’ (Italy) (+ mancozeb + iprovalicarb) (Bayer CropScience, Bayer CropScience, Bayer CropScience) ; ‘Mikal Premium’ (Spain) (+ mancozeb + iprovalicarb) (Bayer CropScience, Bayer CropScience, Bayer CropScience) ; ‘Mildex’ (+ fenamidone) (Bayer CropScience, Bayer CropScience) ; ‘R6 Triplo’ (+ cymoxanil + mancozeb) (Bayer CropScience, Bayer CropScience, Bayer CropScience) ; ‘Rhodax’ (+ mancozeb) (Bayer CropScience, Bayer CropScience) ; ‘Rhodax Express’ (+ mancozeb) (Philagro, Philagro) ; ‘Rhodax M’ (+ mancozeb) (Philagro, Philagro) ; ‘Sillage’ (+ metiram) (BASF, BASF) ; ‘Tertio’ (+ fenamidone + cymoxanil) (Bayer CropScience, Bayer CropScience, Bayer CropScience) ; ‘Valiant’ (+ cymoxanil + folpet) (Bayer CropScience, Bayer CropScience, Bayer CropScience) ; ‘ViteneTriplo’ (+ cymoxanil + mancozeb) (Sipcam S.p.A., Sipcam S.p.A., Sipcam S.p.A.) ; ‘Vitipec Gold’ (+ cymoxanil + folpet) (Sapec, Sapec, Sapec) Discontinued products ‘Terronate *’ (Agriliance) mixtures ‘Aliette-C *’ (+ captan) (Nippon Soda, Nippon Soda) ; ‘Carlit *’ (+ benalaxyl + mancozeb) (Aventis, Aventis, Aventis)
fosetyl
mixtures ‘Previcur Energy’ (+ propamocarb) (Bayer CropScience, Bayer CropScience)
ANALYSIS
Product analysis by iodometric potentiometric titration (CIPAC Handbook, 1995, G, 82–88), or by ion chromatography with conductivity detection (ibid., 2000, J, 66). Residues determined by glc of the parent compound and its metabolite. See also Pestic. Anal.Man., II, 180.415; Resid.Anal.Methods. Details of methods are available from Bayer CropScience.
ENVIRONMENTAL FATE
Animals Fosetyl-aluminium is almost completely absorbed and undergoes extensive metabolic transformation. The major end-products, CO2 and phosphorous acid, are excreted in expired air and urine, respectively. Plants The metabolism of fosetyl-aluminium in plants proceeds through the hydrolytic cleavage of the ethyl ester bond. Phosphorous acid is detected as the major metabolite. Soil/Environment In soil, fosetyl-aluminium has an extremely short half-life under both aerobic and anaerobic conditions, with rapid dissipation and metabolism; DT50 (aerobic) 20 min to 1.5 h. In microbially active water/sediment systems, fosetyl-aluminium is rapidly degraded; DT50 14–40 h.
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EU Rev. Rep.SANCO/10015/06; EFSA Sci. Rep. (2005) 54, 1–79. EU Status (1107/2009) Approved, 2006/64/EC.
MAMMALIAN TOXICOLOGY
fosetyl-aluminium
Oral Acute oral LD50 for rats >7080 mg/kg.Skin and eye Acute percutaneous LD50 for rats and rabbits >2000 mg/kg. Non-irritating to skin.Inhalation LC50 (4 h) for rats >5.11 mg/l air.NOEL NOAEL (2 y) for dogs 300 mg/kg b.w. daily.ADI (EC) 3 mg/kg b.w. [2006]; (EPA) 2.5 mg/kg b.w. [2003].Other Non-teratogenic, non-mutagenic and non-carcinogenic.Toxicity class WHO (a.i.) U EPA (formulation) IIIEC classification Xi; R41
ECOTOXICOLOGY
fosetyl-aluminium
Birds Acute oral LD50 for bobwhite quail >8000 mg/kg.Dietary LC50 (5 d) for bobwhite quail and mallard ducks >20 000 ppm diet.Fish LC50 (96 h) for rainbow trout >122, bluegill sunfish >60 mg/l. Daphnia LC50 (48 h) >100 mg/l. Algae EC50 (90 h) for Scenedesmuspannonicus 21.9 mg/l.Other aquatic spp. NOEC (21 d) for Chironomus 100.2 mg/l. Bees LD50 (96 h, oral) >461.8 µg/bee; (contact) >1000 µg/bee.Worms LC50 (14 d) >1000 mg/kg.

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