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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24984836Curator'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 |
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24984836
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0006749 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29310040 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10477344
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
Edited
Fri Dec 15 19:52:46 GMT 2023
by
admin
on
Fri Dec 15 19:52:46 GMT 2023
|
Record UNII |
J718M71A7A
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | ||
|
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 | |||
|
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 | |||
|
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 |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |