Chlorothalonil
(Synonyms: 百菌清) 目录号 : GC47082
A broad-spectrum organochlorine fungicide
Cas No.:1897-45-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Chlorothalonil is a broad-spectrum organochlorine fungicide that forms adducts with glutathione 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.
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 pastorianusPestic. 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 derivativesBioorg. 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 rhizomePest. 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 henryiJ. 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 speciesMar. 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 relevanceRegul. Toxicol. Pharmacol.24(1 Pt 1)69-84(1996)
| Cas No. | 1897-45-6 | SDF | |
| 别名 | 百菌清 | ||
| Canonical SMILES | ClC1=C(C#N)C(Cl)=C(Cl)C(Cl)=C1C#N | ||
| 分子式 | C8Cl4N2 | 分子量 | 265.9 |
| 溶解度 | DMSO: Slightly Soluble,Methanol: Slightly Soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.7608 mL | 18.8041 mL | 37.6081 mL |
| 5 mM | 0.7522 mL | 3.7608 mL | 7.5216 mL |
| 10 mM | 0.3761 mL | 1.8804 mL | 3.7608 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Regulation of Chlorothalonil degradation by molecular hydrogen
J Hazard Mater 2022 Feb 15;424(Pt A):127291.PMID:34583156DOI:10.1016/j.jhazmat.2021.127291.
Pesticides can accumulate throughout the food chain to potentially endanger human health. Although molecular hydrogen (H2) is widely used in industry and medicine, its application in agriculture is just beginning. This study showed that H2 enhances the degradation of the fungicide Chlorothalonil (CHT) in plants, but does not reduce its antifungal efficacy. Pharmacological evidence confirmed the contribution of H2-stimulated brassinosteroids (BRs) in the above responses. The genetic increased endogenous H2 with overexpression of hydrogenase 1 gene (CrHYD1) from Chlamydomonas reinhardtii in Arabidopsis not only increased BRs levels, but also eventually intensified the degradation of CHT. Expression of genes encoding some enzymes responsible for detoxification in tomato and Arabidopsis were also stimulated. Contrasting responses were observed after the pharmacological removal of endogenous BR. We further proved that H2 control of CHT degradation was relatively universal, with at least since its degradation in Chinese cabbage, cucumber, radish, alfalfa, rice, and rapeseed were differentially enhanced by H2. Collectively, above results clearly indicated that both exogenously and endogenously applied with H2 could stimulate degradation of CHT partially via BR-dependent detoxification. These results may open a new window for environmental-friendly hydrogen-based agriculture.
Chlorothalonil: lack of genotoxic potential
Mutat Res 1999 Jan 25;423(1-2):183-6.PMID:10029695DOI:10.1016/s0027-5107(98)00237-1.
Based upon analyses using a number of validated structure-activity relationship models, it is concluded that the carcinogenicity in rodents of Chlorothalonil is not due to a genotoxic mechanism.
The effect of Chlorothalonil on Saccharomyces cerevisiae under alcoholic fermentation
Pestic Biochem Physiol 2022 Mar;182:105032.PMID:35249653DOI:10.1016/j.pestbp.2021.105032.
Chlorothalonil is a broad-spectrum fungicide largely used for the control of several diseases of grapevines. With a moderate persistence in plants, soil and, water, it can be carried to grape musts, particularly when applied to control grape rot diseases. This work aimed to determine the effect of Chlorothalonil on Saccharomyces cerevisiae under fermentative conditions using a flow cytometry approach. Yeasts were cultivated in synthetic must with different concentrations of Chlorothalonil (0 to 60 μM) and evaluated for culture-ability, membrane integrity, reactive oxygen species (ROS) accumulation, mitochondrial membrane potential, metacaspase activity, ATP, nonprotein SH and, SH-proteins. The results confirmed the oxidation of nonprotein SH, including glutathione, and the binding of the fungicide with sulfhydryl proteins, which led to changes in the cell and mitochondrial membranes that result in the necrotic death of part of the yeast population, and a reduction in metabolic activity. Moreover, the reduction in glutathione-SH concentration was responsible for the increase in ROS which in turn triggers metacaspase-dependent apoptotic cell death. Cells that escape death adapt and began to grow and ferment after a dose-dependent lag-phase period, exhibiting an almost normal fermentative behavior thereafter. Moreover, was observed unexpected protection of Chlorothalonil sub-dosages on yeast cell membrane integrity during alcoholic fermentation. This study contributed insights into how Chlorothalonil leads the non-target organism S. cerevisiae to cell death and explores the effect of the fungicide during alcoholic fermentation.
Flavonoid-sensitized photolysis of Chlorothalonil in water
Pest Manag Sci 2020 Sep;76(9):2972-2977.PMID:32246548DOI:10.1002/ps.5842.
Background: Chlorothalonil is a conventional chloroaromatic fungicide and is toxic to many aquatic species. This study was designed to investigate the effects of six flavonoids on the photolysis of Chlorothalonil under sunlight and artificial light. Results: Flavonoids sensitized the photolysis of Chlorothalonil under sunlight and artificial light by 6.7-18.3 and 2.4-7.5 times, respectively, in comparison with a flavonoid-free control. Photosensitization effect of each of the six flavonoids was greater under sunlight irradiation than under high-pressure mercury lamp irradiation. Cyanidin showed greater photosensitization effects than luteolin, galangin, quercetin, morin and kaempferol. Chlorothalonil underwent photo-reductive dechlorination and no hydrolysis product was formed in the presence of flavonoids. Hydroxyl and hydrogen radicals were detected in the absence and presence of cyanidin, respectively, under light irradiation. Conclusion: The photosensitization effect of flavonoids on Chlorothalonil photolysis is apparently related to flavonoid structure and might be due to their hydrogen donation capacity. These results highlight benefit of using flavonoids to manage aquatic pollution and reduce aquatic toxicity, and have great relevance in predicting the degradation kinetics and biological impacts of Chlorothalonil in surface water. © 2020 Society of Chemical Industry.
Environmental fate and toxicology of Chlorothalonil
Rev Environ Contam Toxicol 2014;232:89-105.PMID:24984836DOI:10.1007/978-3-319-06746-9_4.
Chlorothalonil is a broad spectrum, non systemic, organochlorine pesticide that was first registered in 1966 for turf grasses, and later for several food crops. Chlorthalonil has both a low Henry's law constant and vapor pressure, and hence, volatilization losses are limited. Although, Chlorothalonil's water solubility is low, studies have shown it to be highly toxic to aquatic species. Mammalian toxicity (to rats and mice) is moderate, and produces adverse effects such as, tumors, eye irritation and weakness. Although, there is no indication that Chlorothalonil is a human carcinogen,there is sufficient evidence from animal studies to classify it as a probable carcinogen.Chlorothalonil has a relatively low water solubility and is stable to hydrolysis.However, hydrolysis under basic conditions may occur and is considered to be a minor dissipation pathway. As a result of its high soil adsorption coefficient this fungicide strongly sorbs to soil and sediment. Therefore, groundwater contamination is minimal. Degradation via direct aqueous or foliar photolysis represents a major dissipation pathway for this molecule, and the photolysis rate is enhanced by natural photosensitizers such as dissolved organic matter or nitrate. In addition to photolysis, transformation by aerobic and anaerobic microbes is also a major degradation pathway. Under anaerobic conditions, hydrolytic dechlorination produces the stable metabolite 4-hydroxy-2,5,6-trichloroisophthalonitrile. Chlorothalonil is more efficiently degraded under neutral pH conditions and in soil containing a low carbon content.