Dimethomorph

TC & FORMULATION: 95%TC, 69%WP, 50%WP, 80%WDG

Structure Formula

NOMENCLATURE

Common name dimethomorph (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. 404-200-2

PHYSICAL CHEMISTRY

Composition (E)- to (Z)- ratio is c. 1:1.  Mol. wt. 387.9  M.f. C21H22ClNO4  Form Colourless to off-white powder to crystals.  M.p. 125.2-149.2 ºC; (E)- isomer 136.8-138.3 ºC; (Z)- isomer 166.3-168.5 ºC  V.p. (E)- isomer 9.7 ´ 10-4 mPa; (Z)- isomer 1.0 ´ 10-3 mPa (both 25 ºC)  KOW logP = 2.63 (E)- isomer; 2.73 (Z)- isomer (both 20 ºC)  Henry (E)- isomer 5.4 ´ 10-6 Pa m3 mol-1; (Z)- isomer 2.5 ´ 10-5 Pa m3 mol-1  S.g./density Bulk density 1318 kg/m3 (20 ºC)  Solubility In water 81.1 (pH 5), 49.2 (pH 7), 41.8 (pH 9) (all in mg/l, 20 °C). In n-heptane 0.12 (E), 0.053 (Z); xylene 22.2 (E), 6.4 (Z); 1,2-dichloroethane 182.5 (E), 92.5 (Z); ethyl acetate 46.6 (E), 9.5 (Z); acetone 105.6 (E), 18 (Z), methanol 33.5 (E), 7.5 (Z) (all in mg/l). In n-hexane 0.11, methanol 39, ethyl acetate 48.3, toluene 49.5, acetone 100, dichloromethane 461 (all for (EZ), in mg/l).  Stability Hydrolytically and thermally stable under normal conditions. Stable for >5 years in the dark. The (E)- and (Z)- isomers are interconverted in sunlight.  pKa -1.305 (calc.)  F.p. Not flammable 

APPLICATIONS

Biochemistry Inhibits the formation of the oomycete fungal cell wall.  Mode of action Local 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.  Uses Fungicide 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 formulated product/ha. Formulation types DC; WG; WP.

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