A broad-spectrum organochlorine fungicide
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Chlorothalonil

Item No. 24142

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2,4,5,6-tetrachloro-1,3-benzenedicarbonitrile
CAS Number
1897-45-6
Synonyms
  • 2,4,5,6-Tetrachloroisophthalonitrile
Molecular Formula
C8Cl4N2
Formula Weight
265.9
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Slightly SolubleMethanol: Slightly Soluble
SMILES
ClC1=C(C#N)C(Cl)=C(Cl)C(Cl)=C1C#N
InChi Code
InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
InChi Key
CRQQGFGUEAVUIL-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    100 mg

    $41

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    Product Description

    Chlorothalonil is a broad-spectrum organochlorine fungicide that forms adducts with glutathione (GST; Item No. 10007461) and cysteine residues on enzymes leading to GST depletion and enzyme deactivation, respectively.1 In vitro, it inhibits the growth of C. albicans and C. orbiculare fungi, S. aureus and B. cereus Gram-positive bacteria, and E. coli and P. aeruginosa Gram-negative bacteria (MICs = 0.7, 5, 1.3, 0.7, 0.5, and 1.7 µg/ml, respectively).2,3 In vivo, chlorothalonil (100 µg/ml) completely inhibits the growth of P. infestans, the tomato late blight pathogen, on tomato plants.4 It is toxic to aquatic organisms, including species of fish, crustaceans, molluscs, and algae with tenth percentile of toxicity values of 25.23, 40.59, 0.69, and 3.94 µg/L, respectively, as well as to other aquatic invertebrates.5 Chlorothalonil is carcinogenic in animal models and induces neoplasms in the forestomach and kidneys of rats when administered at a dose of 3.8 mg/kg per day, but it is not genotoxic.6 Formulations containing chlorothalonil have been used as fungicides in agriculture.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Tillman, R.W., Siegel, M.R., and Long, J.W. Mechanism of action and fate of the fungicide chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) in biological systems. I. Reactions with cells and subcellular components of Saccharomyces pastorianus. Pestic. Biochem. Physiol. 3(2), 160-167 (1973).

    2. Shi, L.-P., Jiang, K.-M., Jiang, J.-J., et al. Synthesis and antimicrobial activity of polyhalobenzonitrile quinazolin-4(3H)-one derivatives. Bioorg. Med. Chem. Lett. 23(21), 5958-5963 (2013).

    3. Lee, J.Y., Moon, S.S., and Hwang, B.K. Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome. Pest. Manag. Sci. 61(8), 821-825 (2005).

    4. Lee, Y.M., Moon, J.S., Yun, B.-S., et al. Antifungal activity of CHE-23C, a dimeric sesquiterpene from Chloranthus henryi. J. Agric. Food. Chem. 57(13), 5750-5755 (2009).

    5. DeLorenzo, M.E., and Fulton, M.H. Comparative risk assessment of permethrin, chlorothalonil, and diuron to coastal aquatic species. Mar. Pollut. Bull. 64(7), 1291-1299 (2012).

    6. Wilkinson, C.F., and Killeen, J.C. A mechanistic interpretation of the oncogenicity of chlorothalonil in rodents and an assessment of human relevance. Regul. Toxicol. Pharmacol. 24(1 Pt 1), 69-84 (1996).