Common Name

Dimethomorph

 

IUPAC

(EZ)-4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl]morpholine

 

CAS

4-[3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]morpholine

 

CAS No.

110488-70-5

 

Molecular Formula

C₂₁H₂₂ClNO₄

General Product Information

 

 

Category

Fungicides > Morpholine fungicides

 

Activity

Fungicide.
Dimethomorph has protectant and curative activity, but is best used as a prophylactive in disease control programmes. Application intervals should be 10-14 days. It controls soil- and air-borne oomycete diseases. It is locally systemic and exhibits translaminar activity following foliar application. Dimethomorph is rainfast and has residual activity. The product can also be applied as a soil drench for root uptake. Dimethomorph controls all actively growing stages of fungi of the order Peronosporales, especially potato late blight. It is known to interfere with the formation of cell walls but the exact biochemical target has not yet been identified. In field trials, alcohol ethoxylate adjuvants have been shown to enhance the activity of the fungicide against downy mildew.

The company recommends that dimethomorph is not used alone in disease control programmes to delay the onset of resistance. Crops should be treated with combination products, tank mixes or in sequence with other products, e.g. mancozeb. The product is non-phytotoxic to target crops and safe to beneficial insects.

 

CropUse

Crop uses: 
vines, potatoes, tomatoes, tobacco, vegetables 
 

 

Premix

Chlorothalonil+dimethomorph
Dimethomorph+mancozeb
Pyraclostrobin+dimethomorph
Dimethomorph+ametoctradin
Fluazinam+dimethomorph
Azoxystrobin+Dimethomorph
Propineb+Dimethomorph
Dimethomorph+Metalaxyl
Dimethomorph+Copper calcium sulphate
Dimethomorph+Metiram
Cuprous oxide+Dimethomorph

 

 

Dispersible concentrate, suspension concentrate, wettable powder. Premix Parters: tetradifon.

 

Physical & Safety Data

 

 

Physical Properties

Molecular weight:387.9; Physical form:Colourless to grey crystalline powder. Density:Bulk density 1318 kg/m3 (20 °C); Composition:(E)- to (Z)- ratio is c. 1:1. Melting point:127-148 °C; (E)- isomer 135.7-137.5 °C; (Z)- isomer 169.2-170.2 °C; Vapour pressure:(E)- isomer 9.7×10-4 mPa; (Z)- isomer 1.0×10-3 mPa (both 25 °C); Partition coefficient(n-octanol and water):logP = 2.63 (E)- isomer; 2.73 (Z)- isomer (both 20 °C); Solubility:In 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), dimethylformam; Stability:Hydrolytically and thermally stable under normal conditions. Stable for >5 years in the dark. The (E)- and (Z)- isomers are interconverted in sunlight.

 

Toxicology

Oral:Acute oral LD₅₀ for male rats 4300 mg/kg, female rats 3500 mg/kg, male mice >5000 mg/kg, female mice 3700 mg/kg b.w. Percutaneous:Acute percutaneous LD₅₀ for rats >5000 mg/kg b.w. Not irritant to skin or eyes of rabbits. Not a skin sensitiser (guinea pigs). Inhalation: LC₅₀ (4 h) for rats >4.2 mg/l air. ADI:() 0.002 mg/kg b.w. (sum of dimethoate and omethoate

 

Environmental Profile

Ecotoxicology:?
Algae: EC₅₀ (96 h) >20 mg/l.Bees:Non-toxic to honeybees at 0.1 mg/bee (contact or oral, highest dose tested).Birds:Acute oral LD₅₀ for mallard ducks >2000 mg/kg. Dietary LC₅₀ >5300 ppm.Daphnia: EC₅₀ (48 h) 49 mg/l.Fish: LC₅₀ (96 h) for bluegill sunfish >25, carp 14, rainbow trout 3.4 mg/l.Worms: EC₅₀ for earthworms >1000 mg/kg soil.?
Environmental fate:?
Animals:In rats, the major route of metabolism is demethylation of one of the dimethoxy groups or by oxidation of one of the CH₂ groups (ortho- or meta- position) of the morpholine ring. The major route of excretion was the faeces.Soil:Moderately mobile ( K_d 2.09-11.67 ml/g, K_oc 290-566). Aerobic soil metabolism 50 66-117 d; no degradates identified except for CO₂.Plant:The only significant component of the residue, when present, is the parent compound.
WATER SOLUBILITY: 18 mg/l at 20°C (pH 7).

Fate in soil: 
The half-life of dimethomorph is 14-50 days. The compound has low soil mobility and is not expected to leach.

Fate in aquatic systems: 
Dimethomorph is slowly degraded by photolysis in water.

 

Transport Information

Signal Word:CAUTION; Hazard Class:III (Slightly hazardous)