Chlorothalonil

Chlorothalonil
Names

Preferred IUPAC name 2,4,5,6-Tetrachlorobenzene-1,3-dicarbonitrile
Other names 2,4,5,6-Tetrachloroisophthalonitrile Bravo Daconil Tetrachloroisophthalonitrile Celeste Bronco Agronil Aminil
Identifiers
CAS Number	1897-45-6^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:3639^N
ChEMBL	ChEMBL468167^N
ChemSpider	13861400^Y
ECHA InfoCard	100.015.990
KEGG	C11037^N
RTECS number	NT2600000
UNII	J718M71A7A^N
InChI InChI=1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14^Y Key: CRQQGFGUEAVUIL-UHFFFAOYSA-N^Y
SMILES Clc1c(C#N)c(Cl)c(C#N)c(Cl)c1Cl
Properties
Chemical formula	C₈Cl₄N₂
Molar mass	265.91 g mol⁻¹
Appearance	white crystalline solid
Density	1.8 g cm⁻³, solid
Melting point	250 °C (482 °F; 523 K)
Boiling point	350 °C (662 °F; 623 K) (760 mmHg)
Solubility in water	0.06 g/100 ml
log P	2.88–3.86
Related compounds
Related nitriles; organochlorides	benzonitrile; hexachlorobenzene, dichlorobenzene, chlorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

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-containing products are sold under the names Bravo, Echo, and Daconil. It was first registered for use in the US in 1966. In 1997, the most recent year for which data are available, it was the third most used fungicide in the US, behind only sulfur and copper, with some 12 million pounds used in agriculture alone that year. Including nonagricultural uses, the EPA estimates, on average, almost 15 million pounds were used annually from 1990-1996.

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.

Chlorothalonil reduces fungal intracellular glutathione molecules to alternate forms which cannot participate in essential enzymatic reactions, ultimately leading to cell death, similar to the mechanism of trichloromethyl sulfenyl.

According to the United States Environmental Protection Agency, chlorothalonil is a toxicity category I eye irritant, producing severe eye irritation. It is in toxicity category II, "moderately toxic", if inhaled (inhaled LD₅₀ 0.094 mg/l in rats.) For skin contact and ingestion, chlorothalonil is rated toxicity category IV, "practically nontoxic", meaning the oral and dermal LD₅₀ is greater than 10,000 mg/kg.

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