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Details

Stereochemistry ACHIRAL
Molecular Formula C8Cl4N2
Molecular Weight 265.911
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHLOROTHALONIL

SMILES

ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl

InChI

InChIKey=CRQQGFGUEAVUIL-UHFFFAOYSA-N
InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27495920 | https://www.ncbi.nlm.nih.gov/pubmed/29310040 | https://www.ncbi.nlm.nih.gov/pubmed/10477344 |

Chlorothalonil (2,4,5,6-tetrachloroisophthalonitrile) is an organic compound mainly used as a broad spectrum, nonsystemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. Chlorothalonil reduces fungal intracellular glutathione molecules to alternate forms which cannot participate in essential enzymatic reactions, ultimately leading to cell death. Chlorothalonil is slightly toxic to mammals, but it can cause severe eye and skin irritation in certain formulations. Very high doses may cause a loss of muscle coordination, rapid breathing, nose bleeding, vomiting, and hyperactivity. Dermatitis, vaginal bleeding, bright yellow and/or bloody urine, and kidney tumors may also occur, followed by death. In a number of tests of varying lengths of time, rats which were fed a range of doses of chlorothalonil generally showed no effects on physical appearance, behavior, or survival. Kidney changes such as kidney enlargement were common. In the US, chlorothalonil is used predominantly on peanuts (about 34% of usage), potatoes (about 12%), and tomatoes (about 7%), though the EPA recognizes its use on many other crops. It is also used on golf courses and lawns (about 10%) and as a preservative additive in some paints (about 13%), resins, emulsions, and coatings. Chlorothalonil is commercially available in many different formulations and delivery methods. It is applied as a dust, dry or water-soluble grains, a wettable powder, a liquid spray, a fog, and a dip. It may be applied by hand, by ground sprayer, or by aircraft

Originator

Sources: Boletin. Sociedad Chilena de Obstetricia y Ginecologia (1954), 19, (7), 173.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Mycorrhizal growth in pure cultures in the presence of pesticides.
2002
Adsorption-desorption studies of alachlor, metolachlor, EPTC, chlorothalonil and pirimiphos-methyl in contrasting soils.
2002 Apr
Environmental fate of metalaxyl and chlorothalonil applied to a bentgrass putting green under southern California climatic conditions.
2002 Apr
Free radicals in antigen formation: reduction of contact allergic response to hydroperoxides by epidermal treatment with antioxidants.
2002 Apr
Antifouling paint booster biocide contamination in Greek marine sediments.
2002 Aug
Degradation of chlorpyrifos, fenamiphos, and chlorothalonil alone and in combination and their effects on soil microbial activity.
2002 Dec
Transformation of the fungicide chlorothalonil by Fenton reagent.
2002 Dec 18
Effects of currently used pesticides in assays for estrogenicity, androgenicity, and aromatase activity in vitro.
2002 Feb 15
Foot transfer of lawn-applied pesticides from turf to carpet: comparison of semivolatile chlorpyrifos with nonvolatile chlorothalonil.
2002 Jan
[Time-specific infection rate of Beauveria bassiana on Myzus persicae after topical inoculation of conidial suspension].
2002 Jun
Quantitative PCR monitoring of the effect of azoxystrobin treatments on Mycosphaerella graminicola epidemics in the field.
2002 Mar
Interlaboratory comparison of pesticide recovery from water using solid-phase extraction disks and gas chromatography.
2002 Nov-Dec
Determination of antifouling compounds in marine sediments by solid-phase microextraction coupled to gas chromatography-mass spectrometry.
2003 Aug 22
Effects of currently used pesticides in the AhR-CALUX assay: comparison between the human TV101L and the rat H4IIE cell line.
2003 Dec 15
SBSE-GC-ECD/FPD in the analysis of pesticide residues in Passiflora alata Dryander herbal teas.
2003 Jan 1
Pesticide degradation in a 'biobed' composting substrate.
2003 May
Comparative toxicity of chlorothalonil: Ceriodaphnia dubia and Pimephales promelas.
2003 Nov
Analysis of pesticide residues in lettuce by large volume-difficult matrix introduction-gas chromatography-time of flight-mass spectrometry (LV-DMI-GC-TOF-MS).
2003 Oct
Atmospheric deposition of pesticides to an agricultural watershed of the Chesapeake Bay.
2003 Sep-Oct
[Pesticide use and poisoning among farmers from the county of Paty do Alferes, Rio de Janeiro, Brazil].
2004 Jan-Feb
Chlorothalonil-biotransformation by glutathione S-transferase of Escherichia coli.
2004 Mar
Low-dose agrochemicals and lawn-care pesticides induce developmental toxicity in murine preimplantation embryos.
2004 May
Foliar and soil deposition of pesticide sprays in peanuts and their washoff and runoff under simulated worst-case rainfall conditions.
2004 Nov 17
Empirical and modeling evidence of regional atmospheric transport of current-use pesticides.
2004 Oct
Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi.
2004 Oct 6
Application of solvent microextraction in a single drop for the determination of new antifouling agents in waters.
2004 Sep 17
Dissipation of chlorothalonil, chlorpyrifos, and profenofos in a Malaysian agricultural soil: a comparison between the field experiment and simulation by the PERSIST model.
2005
Behavioral and sex ratio modification of Japanese medaka (Oryzias latipes) in response to environmentally relevant mixtures of three pesticides.
2005 Feb
Pesticide residues on the external surfaces of field crop sprayers: occupational exposure.
2005 Jun
HER-2/neu and CD117 (c-kit) overexpression in patients with pesticide exposure and extensive stage small cell lung carcinoma (ESSCLC).
2005 Jun 9
Wet deposition of current use pesticides at a rural location on the Delmarva Peninsula: impact of rainfall patterns and agricultural activity.
2005 Oct 5
Ambient air concentrations of pesticides used in potato cultivation in Prince Edward Island, Canada.
2006 Feb
Pollutant effects on Pacific oyster, Crassostrea gigas (Thunberg), hemocytes: screening of 23 molecules using flow cytometry.
2006 Jan
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Patents

Sample Use Guides

In Vivo Use Guide
Sources: U.S. Environmental Protection Agency. 1984. Chlorothalonil: Fact Sheet Number 36. September 30, 1984. Washington, DC.
n a two-year dietary rat study, the lowest dose of chlorothalonil that produced no adverse effects in the animals was 60 ppm (3 mg/kg)
Route of Administration: Oral
CHO-K1 cells were exposed to the tested compounds for 1 h in the absence of FCS. Etoposide was dissolved in physiological saline and chlorothalonil in dimethylsulfoxyde. The dose range was chosen in order to obtain both damaged and highly damaged cells observed in a dose range-finding study. Control cultures were incubated in the same conditions in the presence of respective solvent. Following drug treatment, cells were rinsed twice in PBS, trypsinized and resuspended in complete medium.
Name Type Language
CHLOROTHALONIL
HSDB   ISO   MI  
Common Name English
CHLOROTHALONIL [ISO]
Common Name English
BRAVO
Brand Name English
DACONIL
Common Name English
M-TETRACHLOROPHTHALODINITRILE
Common Name English
CHLOROTHALONIL [MI]
Common Name English
2,4,5,6-TETRACHLORO-1,3-BENZENEDICARBONITRILE
Systematic Name English
DAC-2787
Code English
CHLOROTHALONIL [IARC]
Common Name English
CHLOROTHALONIL [HSDB]
Common Name English
DACONIL 2787
Brand Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 81901
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID0020319
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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WIKIPEDIA
CHLOROTHALONIL
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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HSDB
1546
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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PUBCHEM
15910
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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FDA UNII
J718M71A7A
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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CHEBI
3639
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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ALANWOOD
chlorothalonil
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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SMS_ID
100000141987
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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MERCK INDEX
m3439
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
PRIMARY Merck Index
EVMPD
SUB107721
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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ECHA (EC/EINECS)
217-588-1
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
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CAS
1897-45-6
Created by admin on Fri Dec 15 19:52:46 GMT 2023 , Edited by admin on Fri Dec 15 19:52:46 GMT 2023
PRIMARY