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Fungicides

Current Location: Home > Products > Fungicides

Epoxiconazole

FRAC 3, G1 SBI Class I, DMI: triazole

NOMENCLATURE
Common name époxiconazole ((m) F-ISO); epoxiconazole (BSI, E-ISO) IUPAC name (2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
Chemical Abstracts name cis-1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole CAS RN [133855–98–8], formerly [106325–08–0] and [205862–63–1]; [135319–73–2] stereochemistry undefined EC no. 406–850–2 Development codes BAS 480F (BASF) Smiles code Fc1ccc(cc1)C2(Cn3cncn3)OC2c4ccccc4Cl
PHYSICAL CHEMISTRY
Composition Material is the 2R,3S- 2S,3R- enantiomer pair. Mol. wt. 329.8 M.f. C17H13ClFN3O Form Colourless crystals. M.p. 136.2–137 °C V.p. <0.01 mPa (20 °C) Kow logP = 3.33 (pH 7) Henry <4.71 × 10-4Pa m3 mol-1 (calc.) S.g./density 1.384 (room temperature) Solubility In water 6.63 × 10-4 g/100 ml (20 °C). In acetone 14.4, dichloromethane 29.1, heptane 0.04 (all in g/100 ml). Stability No hydrolysis at pH 5 and pH 7 within 12 days.
COMMERCIALISATION
History Developed and introduced by BASF AG (now BASF SE); first registrations in 1993. Patents EP 94564; US 4464381 Manufacturers BASF; Astec; Cheminova; Feixiang; Fertiagro; Flagchem; Huifeng Agrochemical; Shanghai Shengnong; Sinon
APPLICATIONS
Biochemistry Inhibition of C-14-demethylase in sterol biosynthesis. Mode of action Preventive and curative fungicide.Uses Broad-spectrum Fungicide, with preventive and curative action, for control of diseases caused by Ascomycetes, Basidiomycetes and Deuteromycetes in bananas, cereals, coffee, rice, corn, peanut and sugar beet, generally at 125 g/ha. Formulation types EC; SC; SE. Compatibility Compatible with morpholines, MBC-derivatives, azoles, strobilurins and carboxamides.
PRODUCTS
Selected products ‘Opal’ (BASF) ; ‘Opus’ (BASF, Nufarm Ltd) ; ‘Rubric’ (Cheminova) ; ‘Soprano’ (Makhteshim-Agan) mixtures ‘Allegro’ (+ kresoxim-methyl) (BASF, BASF) ; ‘Champion’ (+ boscalid) (BASF, BASF) ; ‘Opera’ (+ pyraclostrobin) (BASF, BASF) ; ‘Opus Team’ (+ fenpropimorph) (BASF, BASF) ; ‘Swing Gold’ (+ dimoxystrobin) (BASF, BASF) ; ‘Tracker’ (+ boscalid) (BASF, BASF) ; ‘Venture’ (+ boscalid) (BASF, BASF) ; ‘Seguris’ (+ isopyrazam) (Syngenta, Syngenta) ; ‘Adexar’ (+ fluxapyroxad) (BASF, BASF) ; ‘Ceriax’ (+ pyraclostrobin + fluxapyroxad) (BASF, BASF, BASF) ; ‘Osiris’ (+ metconazole) (BASF, BASF) Other products ‘Swing’ (BASF) mixtures ‘Altitud’ (+ fenpropimorph + kresoxim-methyl) (Phyteurop, Phyteurop, Phyteurop) ; ‘Bauxit’ (+ pyraclostrobin) (BASF, BASF) ; ‘Bullseye’ (+ fenpropimorph + kresoxim-methyl) (Agriguard, Agriguard, Agriguard) ; ‘Coach’ (+ pyraclostrobin) (BASF, BASF) ; ‘Density’ (+ kresoxim-methyl + pyraclostrobin) (BASF, BASF, BASF) ; ‘Duett’ (+ carbendazim) (BASF, BASF) ; ‘Eclipse’ (+ fenpropimorph) (BASF, BASF) ; ‘Epoxifen’ (+ fenpropimorph) (Standon, Standon) ; ‘Juwel’ (+ kresoxim-methyl) (BASF, BASF) ; ‘Landmark’ (+ kresoxim-methyl) (BASF, BASF) ; ‘Mantra’ (+ kresoxim-methyl + fenpropimorph) (BASF, BASF, BASF) ; ‘Ogam’ (+ kresoxim-methyl) (BASF, BASF) ; ‘Opponent’ (+ kresoxim-methyl + pyraclostrobin) (BASF, BASF, BASF) ; ‘Optimo’ (+ kresoxim-methyl + pyraclostrobin) (BASF, BASF, BASF) ; ‘Résonance’ (+ fenpropimorph) (Phyteurop, Phyteurop) ; ‘Rex Ultra’ (+ thiophanate-methyl) (BASF, BASF) ; ‘Serial Duo’ (+ kresoxim-methyl) (Agriguard, Agriguard) ; ‘Soprano C’ (+ carbendazim) (Makhteshim-Agan, Makhteshim-Agan) ; ‘Opera Ultra’ (+ pyraclostrobin) (BASF, BASF) ; ‘Envoy’ (+ pyraclostrobin) (BASF, BASF) ; ‘Abacus’ (+ pyraclostrobin) (BASF, BASF) ; ‘Morex’ (+ fluxapyroxad) (BASF, BASF) ; ‘Pexan’ (+ fluxapyroxad) (BASF, BASF) ; ‘Retengo Plus’ (+ pyraclostrobin) (BASF, BASF) ; ‘Viverda’ (+ pyraclostrobin + boscalid) (BASF, BASF, BASF) ; ‘Diamant’ (+ pyraclostrobin + fenpropimorph) (BASF, BASF, BASF) Discontinued products ‘Epic *’ (BASF) mixtures ‘Avalon *’ (+ kresoxim-methyl) (Barclay, Barclay) ; ‘Capricorn *’ (+ carbendazim) (Bayer CropScience, Bayer CropScience) ; ‘KME *’ (+ kresoxim-methyl) (Me2, Me2) ; ‘Landgold Strobilurin KE *’ (+ kresoxim-methyl) (Landgold, Landgold) ; ‘Opus Forte *’ (+ tridemorph) (BASF, BASF) ; ‘Opus Plus *’ (+ tridemorph) (BASF, BASF) ; ‘Riverdance *’ (+ fenpropimorph) (Barclay, Barclay) ; ‘Tango Duo *’ (+ tridemorph) (BASF, BASF)
ANALYSIS
Product analysis by capillary gc with FID (CIPAC Handbook, 2003, K, 38).
ENVIRONMENTAL FATE
Animals A.i. is readily excreted via faeces. There are no major metabolites, but a high number of minor metabolites was identified. The important metabolic reactions were cleavage of the oxirane ring, hydroxylation of the phenyl rings and conjugation. Plants There is extensive degradation. Soil/Environment Degradation in soil is by microbial activity, DT50c. 2–3 mo. Koc 957–2647.
TOXICOLOGICAL & ENVIRONMENTAL REVIEWS
EFSA Sci. Rep. (2008) 138, 1–80. EU Rev. Rep.SANCO/136/08 (2008).EPA Fact Sheet, Aug. 2006. EU Status (1107/2009) Approved, 2008/107/EC.
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 eyes and skin of rabbits.Inhalation LC50 (4 h) for rats >5.3 mg/l air.NOEL (carcinogenicity) for mice 0.81 mg/kg b.w. ADI (EC) 0.008 mg/kg b.w. [2008]; (EPA) aRfD 0.05, cRfD 0.02 mg/kg [2006].EC classification R40| R62| R63| N; R51, R53
ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2000 mg/kg. LC50 for quail 5000 mg/kg.Fish LC50 (96 h) for trout 2.2–4.6, bluegill sunfish 4.6–6.8 mg/kg.Daphnia LC50 (48 h) 8.7 mg/l. Algae EC50 (72 h) for green algae 2.3 mg/l. Bees LD50>100 μg/bee.Worms EC50 (14 d) >1000 mg/kg soil.

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