Dimethomorph Chemical Properties

Melting point:

125-149°C

Boiling point:

584.9±50.0 °C(Predicted)

Density 

1.231±0.06 g/cm3(Predicted)

vapor pressure 

1 x 10^-6 Pa (25 °C)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform: Soluble,Methanol: Soluble

Water Solubility 

50 mg l^-1 (20-23 °C)

pka

-1.19±0.20(Predicted)

form 

Solid

color 

White to off-white

Merck 

13,3248

BRN 

8794474

LogP

2.680

EPA Substance Registry System

Dimethomorph (110488-70-5)

Safety Information

Hazard Codes 

N

Risk Statements 

51/53

Safety Statements 

61

RIDADR 

UN3077 9/PG 3

WGK Germany 

2

RTECS 

QE0478300

Hazardous Substances Data

110488-70-5(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): 321 i.p.; 3900 orally; >5000 dermally; LC50 (4-hr inhalation): >4.2 mg/ml (Veenstra, Owen)

MSDS

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Dimethomorph Usage And Synthesis

Description

Dimethomorph is a cinnamic acid derivative and a member of the morpholine chemical family. Dimethomorph is a mixture of E- and Z-isomers in the ratio of about 1:1 and only the Z-isomer has the fungicidal activity. It fungicidal activity works by the inhibition of sterol (ergosterol) synthesis.
Dimethomorph is a systemic fungicide to protect against various fungal pathogens in vines and other crops. Dimethomorph is used to against downy mildews, late blights, anthracnose, septoria leaf spot, crown rot, and root rot for curbubits, grapevines, head lettuce, onions, potatoes, tomatoes, and fruit including blackberries, raspberries, strawberries.

References

[1] http://www.fao.org
[2] http://pmep.cce.cornell.edu
[3] http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/245.htm

Description

Dimethomorph is a morpholine fungicide that inhibits fungal cell wall formation. It inhibits mycelial growth of the oomycete fungi P. citrophthora, P. parasitica, P. capsici, and P. infestans (EC₅₀s = 0.14, 0.38, <0.1, and 0.16-0.3 μg/ml, respectively) but is less active against the green algae species C. vulgaris or S. obliquus in vitro (EC₅₀s = 47.46 and 44.87 μg/ml, respectively). It inhibits androgen receptor (AR) activity in a reporter assay in MDA-kb2 human breast cancer cells but not in a yeast antiandrogen screen (IC₂₀s = 0.263 and 38.5 μM, respectively). It is not toxic to rats (LD₅₀ = 3,900 mg/kg) or goldfish (C. auratus; LC₅₀ = >32 μg/ml).

Chemical Properties

Off-White Solid

Uses

Agricultural fungicide.

Uses

Dimethomorph is a systemic fungicide which exhibits protectant, curative and antisporulant activities. It is active against fungal diseases such as leaf blight, downy mildew, damping off and foot-rot caused by Phytophthora spp. in/on grapes, potatoes and tomatoes.

Definition

ChEBI: A mixture of (E)- and (Z)-dimethomorph in an unspecified ratio. It is used as a systemic fungicide used on vines, potatoes, and greenhouse crops; only the Z isomer has fungicidal activity.

Agricultural Uses

Fungicide: A systemic fungicide that protects crops from mold. It also kills mold and prevents their spread; controls late blight on tomatoes; and is used as a wood preservative to control downey mildew.

Trade name

ACROBAT® WP; FORUM DC®, [manco- zeb + dimethomorph]; CME 151®; STATURE®

Metabolic pathway

Limited data are available in the open literature. Information presented in this summary is abstracted from the data evaluation published by the Pesticide Safety Directorate (PSD, 1994). Dimethomorph is a (1:l) mixture of the E- and Z-isomers. The Z-isomer has been shown to have all the intrinsic biological activities. The isomerisation of the E- and Z-isomers was observed when resolved isomers were exposed to UV light. Dimethomorph undergoes extensive degradation and metabolism in soil, plants and animals. The major metabolic pathway is the O-demethylation of one of the phenolic methoxy moieties to the corresponding phenols and conjugates. Other metabolic reactions include the oxidation of one of the CH2 moieties of the morpholine ring and the cleavage/opening of the morpholine ring (Scheme 1).

Degradation

Dimethomorph (1) is hydrolytically stable with no observable degradation in pH 4-9 buffered solutions at 70-90 °C for up to 10 weeks.
Degradation occurred when dimethomorph in pH 5 buffer solution was irradiated under Hanau Suntest apparatus (<290 nm) at 25 °C. The calculated aqueous photolytic degradation half-life (DT₅₀) was ca. 25-28 days of continuous irradiation, No sigruficant degradation product (>7% of the applied radioactivity) was identified.

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