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

pka

-1.19±0.20(Predicted)

Water Solubility 

50 mg l^-1 (20-23 °C)

form 

Solid

color 

White to off-white

Merck 

13,3248

BRN 

8794474

Major Application

agriculture
environmental

InChI

1S/C21H22ClNO4/c1-25-19-8-5-16(13-20(19)26-2)18(15-3-6-17(22)7-4-15)14-21(24)23-9-11-27-12-10-23/h3-8,13-14H,9-12H2,1-2H3/b18-14+

InChIKey

QNBTYORWCCMPQP-NBVRZTHBSA-N

SMILES

COc1ccc(cc1OC)\C(=C\C(=O)N2CCOCC2)c3ccc(Cl)cc3

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

Storage Class

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects

Hazard Classifications

Aquatic Chronic 2
Repr. 1B

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

• Language:English Provider:Dimethomorph

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

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.

Uses

Agricultural fungicide.

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®

Synthesis

The first step: xylene and acetic anhydride at room temperature stirring drop of morpholine, drop the end of the slow increase in temperature to 110 ??, reflux insulation 5h, after the end of the over into the distillation kettle desolvation and by-products of acetic acid, the kettle residual part for the intermediate acetyl morpholine The residual part in the kettle is the intermediate acetylmorpholine, the content is more than or equal to 99%, the yield is more than or equal to 90.2%.
The second step: in the reaction kettle into xylene, E-phenyl ketone and amino sodium, stirring temperature to 100 ?? when adding acetomorpholine drops, droplet finished temperature to 110 ?? reflux insulation 2h, insulation end of the temperature to 80 ?? over the wash kettle divided into Out of the waste lye, after washing to neutral water into the distillation kettle recovery of xylene, centrifugal drying enoymorpholine, content greater than or equal to 95%, yield greater than or equal to 76.6%.
In this method, sodium amide is used to replace sodium tert-butoxide in traditional technology, which greatly improves the reaction speed, shortens the reaction time from 10h to 2h, and greatly improves the production efficiency.

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.

References

[1] (EFSA) E F S A. Conclusion regarding the peer review of the pesticide risk assessment of the active substance dimethoate[C]//4 7. 2006. DOI: 10.2903/j.efsa.2006.84r
[2] M E MATHERON  M P. Impact of Azoxystrobin, Dimethomorph, Fluazinam, Fosetyl-Al, and Metalaxyl on Growth, Sporulation, and Zoospore Cyst Germination of Three Phytophthora spp.[J]. Plant disease, 2000, 84 4: 454-458. DOI: 10.1094/pdis.2000.84.4.454
[3] XIAO-BO YU. Aquatic environmental safety assessment and inhibition mechanism of chemicals for targeting Microcystis aeruginosa.[J]. Ecotoxicology, 2014, 23 9: 1638-1647. DOI: 10.1007/s10646-014-1303-x

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