Cymoxanil

Base Information

• Chemical Name: Cymoxanil
• CAS No.: 57966-95-7
• Deprecated CAS: 93195-85-8,1135443-55-8
• Molecular Formula: C7H10N4O3
• Molecular Weight: 198.181
• Hs Code.: 29269090
• European Community (EC) Number: 261-043-0
• UNII: QJO7SS7R8U
• ChEMBL ID: CHEMBL59983
• Mol file: 57966-95-7.mol

Synonyms:2-cyano-N-((ethylamino)carbonyl)-2-(methoxyimino)acetamide;Curzate;Cymoxanil;DPX 3217;DPX 3217 copper sulfate;DPX 3217 fumarate;DPX-3217

Chemical Property of Cymoxanil

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 1.5 x 10-4 Pa (20 °C)
• Melting Point: 160-161oC
• Refractive Index: 1.537
• Boiling Point: 335.48°C (rough estimate)
• PKA: 9.7
• Flash Point: 100 °C
• PSA: 103.58000
• Density: 1.27 g/cm³
• LogP: 0.13988
• Storage Temp.: 0-6°C
• Water Solubility.: 890 mg l-1 (pH 5), 780 mg l-1 (pH 7), unstable at pH 9 at 20 °C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.07529019
• Heavy Atom Count: 14
• Complexity: 301

Purity/Quality:

99% ^*data from raw suppliers

Cymoxanil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn;N,N,Xn
• Statements: 22-43-50/53
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: CCNC(=O)NC(=O)C(=NOC)C#N
• Isomeric SMILES: CCNC(=O)NC(=O)/C(=N/OC)/C#N
• Description: Cymoxanil was first introduced in 1977. It is an acetimide compound used as both a curative and preventative foliar fungicide. In Europe it is being sold for use on grapes, potatoes, tomatoes, hops, sugarbeets and other vegetable crops. Cymoxanil is currently not registered in the U.S. Cymoxanil is a fungicide used on crops including potatoes, tomatoes, and grapes. Cymoxanil is not registered for non-crop use in any country. Cymoxanil's mode of action is as a local systemic. It penetrates rapidly and when inside the plant, it cannot be washed off by rain. It controls diseases during the incubation period and prevents the appearance of damage on the crop. The fungicide is primarily active on fungi belonging to the Peronosporales order: Phytophthora, Plasmopara, and Peronospora. Cymoxanil is a cyanoacetamide fungicide. It inhibits the mycelial growth of 12 isolates of P. infestans with EC50 values of 0.27-0.57 μg/ml. Cymoxanil (5-100 mg/l) inhibits the growth of several strains of S. cerevisiae (IC50s = 8-25 mg/l) but not S. pombe, K. marxianus, P. anomala, or C. utilis. A spray application of cymoxanil (1 mg/mL) one day after inoculation of potato leaves with P. infestans and cucumber leaves with P. cubensis reduces blighted leaves by 79 and 60%, respectively. It is toxic to rats with an acute LD50 value of 3.8 mmol/kg. Formulations containing cymoxanil have been used to prevent fungal growth on crops and treat late potato blight in agriculture.
• Physical Properties: Technical cymoxanil is a peach colored crystalline, odorless solid.
• Uses: Efficient fungicide Cymoxanil is a fungicide applied as a seed treatment or as a foliar application to the plants to control late blight. Agricultural fungicide. Cymoxanil is a foliar applied fungicide which provides preventive and curative control of pathogen species of the order Peronosporales (eg. Phytophthora, Plasmopara and Peronospora) in grapes, potatoes, tomatoes, hops, tobacco and cucurbits.

Technology Process of Cymoxanil

There total 6 articles about Cymoxanil 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: 82.7%

methylene chloride (74-87-3) + 2-cyano oximeacetamide sodium salt → cymoxanil (57966-95-7,93195-85-8)

Guidance literature:

With tetrabutylammomium bromide; In methanol; water; at 20 - 25 ℃; for 3.5h; Reagent/catalyst; Temperature;

Reference yield:

2-cyano-N-(ethylcarbamoyl)acetamide (41078-06-2) → 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide (57966-95-7,93195-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaNO₂ / acetonitrile / 45 °C

2: aq. NaHCO₃ / 50 - 70 °C

With sodium hydrogencarbonate; sodium nitrite; In acetonitrile;

Reference yield:

1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea (41078-09-5) + dimethyl sulfate (77-78-1) → 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide (57966-95-7,93195-85-8)

Guidance literature:

With sodium hydrogencarbonate; at 50 - 70 ℃;

upstream raw materials:

1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea

dimethyl sulfate

methylene chloride

2-cyano-N-(ethylcarbamoyl)acetamide

Downstream raw materials:

1-ethyl-2,4,5-trioxoimidazolidine

acetylamino-cyano-acetic acid

1-ethyl-5-methoxyimino-2,4-dioxoimidazolidine

1-(2,2-dimethyl-5-oxo-4-cyano-3-imidazolin-1-yl)-N-ethyl amide

Refernces

• 1、 -. "Synergistic Combinations Of Active Ingredients". . . Retrieved 2012/02/15.
• 2、 Greci, Lucedio,Carloni, Patricia,Mandrioli, Odofredo,Righi, Lara,Rizzoli, Corrado,Sgarabotto, Paolo. "On the stereochemistry of the synthesis of 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea and its E-configuration crystal structure". . p. 655 - 657. Retrieved 2007/10/03.