Dimethomorph

Base Information

• Chemical Name: Dimethomorph
• CAS No.: 110488-70-5
• Molecular Formula: C₂₁H₂₂ClNO₄
• Molecular Weight: 387.863
• European Community (EC) Number: 404-200-2,600-969-5
• DSSTox Substance ID: DTXSID7034545
• Wikipedia: Dimethomorph
• Wikidata: Q27155626
• ChEMBL ID: CHEMBL3138617
• Mol file: 110488-70-5.mol

Synonyms:4-(3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acryloyl)morpholine;dimethomorph;dimethomorph, (E)-;dimethomorph, (E)-isomer;dimethomorph, (Z)-;dimethomorph, (Z)-isomer

Chemical Property of Dimethomorph

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 1.15E-13mmHg at 25°C
• Melting Point: 125-149 °C
• Refractive Index: 1.58
• Boiling Point: 584.899 °C at 760 mmHg
• Flash Point: 307.536 °C
• PSA: 48.00000
• Density: 1.231 g/cm³
• LogP: 3.58560
• Storage Temp.: 0-6°C
• Water Solubility.: 50 mg l-1 (20-23 °C)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 387.1237359
• Heavy Atom Count: 27
• Complexity: 512

Purity/Quality:

99% ^*data from raw suppliers

Dimethomorph ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: COC1=C(C=C(C=C1)C(=CC(=O)N2CCOCC2)C3=CC=C(C=C3)Cl)OC
• 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. 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).
• Uses: Agricultural fungicide. 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.

Technology Process of Dimethomorph

There total 14 articles about Dimethomorph which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

→ dimethomorph (110488-70-5,113210-98-3)

Guidance literature:

Reference yield: 82.2%

4-acetylmorpholine (1696-20-4) + tert-Amyl alcohol (75-85-4) + sodium tert-pentoxide (14593-46-5) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph (110488-70-5,113210-98-3)

Guidance literature:

With carbon dioxide; In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; paraffin oil;

Reference yield: 73.0%

4-morpholinecarboxaldehyde (4394-85-8) + C16H15ClO2 → dimethomorph (110488-70-5,113210-98-3)

Guidance literature:

With 1,2,3-trimethoxybenzene; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene; at 20 ℃; Irradiation; Inert atmosphere;

DOI:10.1021/acs.orglett.9b03870

upstream raw materials:

4-acetylmorpholine

4-chloro-3',4'-dimethoxy benzophenone

benzene-1,2-diol

4-morpholinecarboxaldehyde

Refernces

• 1、 Lu, Maojian,Lin, Zhaowei,Chen, Shanyi,Chen, Hongyou,Huang, Mingqiang,Cai, Shunyou. "Visible-Light-Enabled Oxidative Coupling of Alkenes with Dialkylformamides to Access Unsaturated Amides". supporting information. p. 9929 - 9933. Retrieved 2019/12/24.
• 2、 -. "FUNGICIDAL MIXTURES". . . Retrieved 2012/04/18.