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Chemical Identification
Common Name
Dimethomorph
中文通用名
烯酰吗啉
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
Molecular Structure
Category
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

Vines

300 g ai/ha

Premix
Pyraclostrobin+dimethomorph
Propineb+Dimethomorph
fluoride ether bacteria amide+Dimethomorph
Fluazinam+dimethomorph
Famoxadone+Dimethomorph
Dithianon+Dimethomorph
Dimethomorph+Propamocarb hydrochloride
Dimethomorph+Oxine-copper
Dimethomorph+Metiram
Dimethomorph+Metalaxyl
Dimethomorph+mancozeb
Dimethomorph+Copper calcium sulphate
Dimethomorph+Benziothiazolinone
Dimethomorph+ametoctradin
Cuprous oxide+Dimethomorph
Chlorothalonil+dimethomorph
Azoxystrobin+Dimethomorph

Type

AI concn

Wettable powder (WP)

50% (w/w)

?

25% (w/w)

Dispersible concentrate (DC)

15% (w/v)

Dispersible concentrate, suspension concentrate, wettable powder. Premix Parters: tetradifon.
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 ( Kd 2.09-11.67 ml/g, Koc 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).

Mallard duck

LD50 >2,000 mg/kg

Bluegill sunfish [96 hrs]

LC50>25 mg/litre

Bobwhite quail

LD50 >2,000 mg/kg

Rainbow trout [96 hrs]

LC506.8 mg/litre

Carp [96 hrs]

LC50 18 mg/litre

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)

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