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Dimethomorph

FRAC 15; cinnamic acid

Dimethomorph NOMENCLATURE

Common namedimethomorph (BSI, draft E-ISO); diméthomorphe ((m) draft F-ISO)

IUPAC name(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine

Chemical Abstracts name(E,Z)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]morpholine

CAS RN[110488-70-5]EEC no.404-200-2Development codesCME 151 (Celamerck); WL 127 294 (Shell); AC 336379 ;CL 183776; CL 336379 (all Cyanamid)

Dimethomorph PHYSICAL CHEMISTRY

Composition(E)- to (Z)- ratio is c. 1:1.Mol. wt.387.9M.f.C21H22ClNO4FormColourless crystals.M.p.127-148 ºC; (E)- isomer 135.7-137.5 ºC; (Z)- isomer 169.2-170.2 ºCV.p.(E)- isomer 9.7 ´ 10-4mPa; (Z)- isomer 1.0 ´ 10-3mPa (both 25 ºC)KOWlogP = 2.63 (E)- isomer; 2.73 (Z)- isomer (both 20 ºC)S.g./densityBulk density 1318 kg/m3(20 ºC)SolubilityIn water 19 (pH 5), 18 (pH 7), 16 (pH 9) (all in mg/l, 20 °C). In acetone 88 (E), 15 (Z), cyclohexanone 27 (Z), dichloromethane 315 (Z), dimethylformamide 272 (E), 40 (Z), hexane 0.04 (E), 0.02 (Z), methanol 7 (Z), toluene 7 (Z) (all in g/l, 20-23 ºC). In n-hexane 0.11, methanol 39, ethyl acetate 48.3, toluene 49.5, acetone 100, dichloromethane 461 (all for (EZ), in mg/l).StabilityHydrolytically and thermally stable under normal conditions. Stable for >5 years in the dark. The (E)- and (Z)- isomers are interconverted in sunlight.

Dimethomorph COMMERCIALISATION

HistoryFungicide reported by G. Albert et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis.,1, 17). Introduced in 1993 by Shell (now BASF AG).PatentsEP 120321; US 5952496.ManufacturersBASF

Dimethomorph APPLICATIONS
BiochemistryInhibits the formation of the oomycete fungal cell wall.Mode of actionLocal systemic fungicide with good protectant and antisporulant activity. Only the (Z)- isomer is intrinsically active, but, because of rapid interconversion of isomers in the light, it has no advantage over the (E)- isomer in practice.UsesFungicide effective against Oomycetes, especially Peronosporaceae and Phytophthora spp. (but not Pythium spp.) in vines, potatoes, tomatoes and other crops. Used in combination with contact fungicides, and applied at 2.0-2.5 kg dimethomorph/ha.Formulation typesDC; WG; WP.Selected tradenames:'Acrobat' (BASF); 'Forum' (BASF)

OTHER TRADENAMES
'Festival' (BASF) mixtures:'Acrobat MZ' (+ mancozeb) (BASF); 'Invader' (+ mancozeb) (BASF)

Dimethomorph ANALYSIS
Product analysis by rp hplc (CIPAC Handbook, 1995, G, 39-46) or capillary gc. Details available from BASF.