Chlorothalonil

Base Information

• Chemical Name: Chlorothalonil
• CAS No.: 1897-45-6
• Deprecated CAS: 101963-73-9,37223-69-1,342632-51-3,216082-57-4,462093-27-2,216082-57-4,342632-51-3,462093-27-2
• Molecular Formula: C8Cl4N2
• Molecular Weight: 265.913
• Hs Code.: 2926.90
• European Community (EC) Number: 217-588-1
• ICSC Number: 0134
• UN Number: 3276,2588
• UNII: J718M71A7A
• DSSTox Substance ID: DTXSID0020319
• Nikkaji Number: J2.133D
• Wikipedia: Chlorothalonil
• Wikidata: Q418320
• Metabolomics Workbench ID: 53065
• ChEMBL ID: CHEMBL468167
• Mol file: 1897-45-6.mol

Synonyms:Bravo;chlorothalonil;Daconil;hydroxychlorothalonil;tetrachloroisophthalonitrile

Chemical Property of Chlorothalonil

Chemical Property:

• Appearance/Colour: White crystal
• Vapor Pressure: 4.36E-05mmHg at 25°C
• Melting Point: 250-251oC
• Refractive Index: 1.632
• Boiling Point: 350.5 °C at 760 mmHg
• Flash Point: 153.8 °C
• PSA: 47.58000
• Density: 1.71g/cm³
• LogP: 4.04356
• Storage Temp.: 0-6°C
• Solubility.: 180mg/L in organic solvents at 20 ℃
• Water Solubility.: 0.6-1.2 mg l-1 (25 °C)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 265.878609
• Heavy Atom Count: 14
• Complexity: 284
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Transportin 1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+,N,Xn,F
• Hazard Codes: T+;N,N,T+,Xn,F
• Statements: 26-37-40-41-43-50/53-36-20/21/22-11
• Safety Statements: 28-36/37/39-45-60-61-36/37-26-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Fungicides
• Canonical SMILES: C(#N)C1=C(C(=C(C(=C1Cl)Cl)Cl)C#N)Cl
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes. The substance is irritating to the respiratory tract. The substance is mildly irritating to the skin.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization.
• Description: Chlorothalonil is a broad-spectrum organic fungicide mainly used to control fungi that threatens a number of agricultural crops, vegetables, trees, fruits, turf and paints, etc. It can also serves as a wood protectant, pesticide, acaricide, which is effective to kill mildew, bacteria, algae, and insects. Besides, it can commercially act as a preservative additive in several paints, resins, emulsions, coatings and can be used on commercial grasses such as golf courses and lawns. Chlorothalonil was first registered by the EPA in 1966. It is environmentally persistent and binds strongly with soil, whose expected half-life in aerobic soils is one to three months. Chlorothalonil functions by reducing the intracellular glutathione molecules of fungal to alternate its forms which affects the essential enzymatic reactions of fungal, ultimately leading to cell death. Chlorothalonil is a pesticide fungicide commonly used in the cultivation of ornamental plants and flowers, rice, and onions. In banana plantations it is used in fumigations by airplanes. It can be used as a preservative of paints and of woods. Chlorothalonil can induce contact urticaria, irritant and allergic contact dermatitis, erythema dychromicum perstans or folliculitis mainly in agricultural workers, in those in wood-related professions or in hortieulturists.
• uses: Chlorothalonil is a fungicide with a broad spectrum of activity used mainly in agriculture but also on turf, lawns and ornamental plants. It protects plants against a variety of fungal infections such as rusts, downy mildew, leaf spot, scabs, blossom blight and black pod. Crops protected include pome fruit, stone fruit, citrus, currants, cranberries, strawberries, bananas, vines, hops, tomatoes, green vegetables, tobacco, coffee, tea, soya bean, groundnuts, potatoes, onions, cereals and sugar beet. In addition, it is used in wood preservatives, fish net coatings and anti-fouling paints.
• Uses: Chlorothalonil is a non-systemic foliar fungicide with protective activity. It is used to control a broad spectrum of fungal diseases in fruit (pome, stone, citrus, etc.), berries, vegetables, cucurbits, root crops, soyabeans, ornamentals and turf. Chlorothalonil is a polychlorinated aromatic broad spectrum non-systematic fungicide. Chlorothalonil is used heavily in agriculture field on crops such as peanuts, potatoes and tomatoes. Chlorothaloni l is a probable human carcinogen (Group B2) and is highly toxic to fish and aquatic invertabrates.

Technology Process of Chlorothalonil

There total 1 articles about Chlorothalonil 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:

→ chlorothalonil (1897-45-6)

Guidance literature:

Reference yield: 95.0%

chlorothalonil (1897-45-6) + aniline (62-53-3) → C14H6Cl3N3 (1142208-21-6)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Green chemistry;

DOI:10.1016/j.bmcl.2013.02.033

Reference yield: 93.0%

chlorothalonil (1897-45-6) + 4-methoxy-aniline (104-94-9) → C15H8Cl3N3O (1142208-32-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 8h; Green chemistry;

DOI:10.1016/j.bmcl.2013.02.033

Downstream raw materials:

4-methoxy-2,5,6-trichloro-1,3-dicyanobenzene

2,4,5-Trichloro-6-propoxy-isophthalonitrile

2,4,5-Trichloro-6-(2-ethyl-hexylamino)-isophthalonitrile

1,3-dicyano-4-hydroxy-2,5,6-trichlorobenzene

Refernces

• 1、 -. "Synergistic Active Compound Combinations Comprising Phenyltriazoles". . . Retrieved 2011/07/29.
• 2、 -. "Protective agents for wood". . . Retrieved 2008/06/13.