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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

Molecular Formula C8Cl4N2
Molecular Weight 265.911
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Solid-phase synthesis of chiral stationary phases based on 2,4,5,6-tetrachloro-1,3-dicyanobenzene derivatives spaced from N-3,5-dinitrobenzoyl alpha-amino acids: comparative study of their resolution efficacy.
2001 Jun
Chlorothalonil and its 4-hydroxy derivative in simple quartz sand soils: a comparison of sorption processes.
2001 Jun 1
Determination of cutin-bound residues of chlorothalonil by immunoassay.
2001 Mar
Multiresidue analysis of pesticides in vegetables and fruits using two-layered column with graphitized carbon and water absorbent polymer.
2001 Sep
Runoff loss of pesticides and soil: a comparison between vegetative mulch and plastic mulch in vegetable production systems.
2001 Sep-Oct
Persistence of chlorpyrifos, fenamiphos, chlorothalonil, and pendimethalin in soil and their effects on soil microbial characteristics.
2002 Aug
Transformation of the fungicide chlorothalonil by Fenton reagent.
2002 Dec 18
Partitioning of selected antifouling biocides in the aquatic environment.
2002 Feb
Foot transfer of lawn-applied pesticides from turf to carpet: comparison of semivolatile chlorpyrifos with nonvolatile chlorothalonil.
2002 Jan
Contact dermatitis caused by pesticides among banana plantation workers in Panama.
2002 Jan-Mar
Quantitative PCR monitoring of the effect of azoxystrobin treatments on Mycosphaerella graminicola epidemics in the field.
2002 Mar
Determination of pesticides and chronic test with Daphnia magna for rainwater samples.
2002 May
Determination of pesticide residues in coconut water by liquid-liquid extraction and gas chromatography with electron-capture plus thermionic specific detection and solid-phase extraction and high-performance liquid chromatography with ultraviolet detection.
2002 May 31
Interlaboratory comparison of pesticide recovery from water using solid-phase extraction disks and gas chromatography.
2002 Nov-Dec
Evaluation of respiratory and cutaneous doses of chlorothalonil during re-entry in greenhouses.
2002 Oct 5
Study of chlorothalonil photodegradation in natural waters and in the presence of humic substances.
2002 Sep
Comparison of five extraction methods for determination of incurred and added pesticides in dietary composites.
2002 Sep-Oct
The multicolored Asian lady beetle, Harmonia axyridis: a review of its biology, uses in biological control, and non-target impacts.
2003
Workplace carcinogen and pesticide exposures in Costa Rica.
2003 Apr-Jun
Degradation of pesticides in biobeds: the effect of concentration and pesticide mixtures.
2003 Aug 27
Urine mutagenicity of farmers occupationally exposed during a 1-day use of chlorothalonil and insecticides.
2003 Feb
Occupational asthma from fungicides fluazinam and chlorothalonil.
2003 Jan
The persistence and degradation of chlorothalonil and chlorpyrifos in a cranberry bog.
2003 Jan 1
Fast supercritical fluid extraction and high-resolution gas chromatography with electron-capture and flame photometric detection for multiresidue screening of organochlorine and organophosphorus pesticides in Brazil's medicinal plants.
2003 Jan 24
How the use of chlorothalonil on golf courses impacts Paenibacillus sp., a pathogen of Ataenius spretulus (Coleoptera: Scarabaeidae).
2003 Jun
Comparative toxicity of chlorothalonil: Ceriodaphnia dubia and Pimephales promelas.
2003 Nov
Atmospheric deposition of pesticides to an agricultural watershed of the Chesapeake Bay.
2003 Sep-Oct
Effects of the agricultural pesticides atrazine, chlorothalonil, and endosulfan on South Florida microbial assemblages.
2004 Apr
Chemical analysis and genotoxicological safety assessment of paper and paperboard used for food packaging.
2004 Aug
[Pesticide use and poisoning among farmers from the county of Paty do Alferes, Rio de Janeiro, Brazil].
2004 Jan-Feb
Glutathione-dependent biotransformation of the fungicide chlorothalonil.
2004 Jun 30
Characterization of complicated new polymorphs of chlorothalonil by X-ray diffraction and computer crystal structure prediction.
2004 Jun 9
Environmental risk limits for antifouling substances.
2004 Mar 10
Low-dose agrochemicals and lawn-care pesticides induce developmental toxicity in murine preimplantation embryos.
2004 May
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
Pesticide patch test series for the assessment of allergic contact dermatitis among banana plantation workers in panama.
2004 Sep
Fate of pesticides during the winemaking process in relation to malolactic fermentation.
2005 Apr 20
Evaluation of fungicides for the control of carrot cavity spot.
2005 Aug
Isolation and antifungal activity of kakuol, a propiophenone derivative from Asarum sieboldii rhizome.
2005 Aug
Pesticide occurrence in selected South Florida canals and Biscayne Bay during high agricultural activity.
2005 Jul 27
Validation of a fast and easy method for the determination of residues from 229 pesticides in fruits and vegetables using gas and liquid chromatography and mass spectrometric detection.
2005 Mar-Apr
Wet deposition of current use pesticides at a rural location on the Delmarva Peninsula: impact of rainfall patterns and agricultural activity.
2005 Oct 5
Dynamics of pesticide residues in the autumn Chinese cabbage (Brassica chinensis L.) grown in open fields.
2006 Apr
Degradation of pesticides in nursery recycling pond waters.
2006 Apr 5
Comparative toxicity of alternative antifouling biocides on embryos and larvae of marine invertebrates.
2006 Aug 31
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
Arbuscular mycorrhizal fungi can alleviate the adverse effects of chlorothalonil on Oryza sativa L.
2006 Sep
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:52:46 GMT 2023
Edited
by admin
on Fri Dec 15 19:52:46 GMT 2023
Record UNII
J718M71A7A
Record Status Validated (UNII)
Record Version
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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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
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ACTIVE MOIETY