Chlorothalonil CAS 1897-45-6
Introduction：Basic information about Chlorothalonil CAS 1897-45-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Chlorothalonil Basic informationDescription uses References
| Product Name: | Chlorothalonil |
| Synonyms: | TPN;1,3-Benzenedicarbonitrile, 2,4,5,6-tetrachloro-;1,3-benzenedicarbonitrile,2,4,5,6-tetrachloro-;1,3-Dicyano-2,4,5,6-tetrachlorobenzene;1,3-Dicyanotetrachlorobenzene;2,4,5,6-Tetrachloro-1,3-benzenedicarbonitrile;BOMBARDIER;BRAVO |
| CAS: | 1897-45-6 |
| MF: | C8Cl4N2 |
| MW: | 265.91 |
| EINECS: | 217-588-1 |
| Product Categories: | Agro-Products;Aromatics;Mutagenesis Research Chemicals;Alpha sort;AromaticsPesticides&Metabolites;C;CAlphabetic;CHMethod Specific;Endocrine Disruptors (Draft);EPA;Fungicides;Pesticides;FUNGICIDE;Organics |
| Mol File: | 1897-45-6.mol |
Chlorothalonil Chemical Properties
| Melting point | 250-251° |
| Boiling point | bp760 350° |
| density | d425 1.7 |
| vapor pressure | 7.6 x 10-5 Pa (25 °C) |
| Fp | 2 °C |
| storage temp. | 0-6°C |
| solubility | 180mg/L in organic solvents at 20 ℃ |
| form | Powder |
| Water Solubility | 0.6-1.2 mg l-1 (25 °C) |
| color | White |
| Odor | odorless in pure form |
| Merck | 14,2166 |
| BRN | 1978326 |
| Exposure limits | An experimental carcinogen. |
| Stability: | Light Sensitive |
| Major Application | agriculture cleaning products cosmetics environmental food and beverages personal care |
| InChI | 1S/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14 |
| InChIKey | CRQQGFGUEAVUIL-UHFFFAOYSA-N |
| SMILES | Clc1c(Cl)c(C#N)c(Cl)c(C#N)c1Cl |
| LogP | 2.94 at 25℃ |
| CAS DataBase Reference | 1897-45-6(CAS DataBase Reference) |
| NIST Chemistry Reference | Tetrachloroisophthalonitrile(1897-45-6) |
| IARC | 2B (Vol. Sup 7, 73) 1999 |
| EPA Substance Registry System | Chlorothalonil (1897-45-6) |
Safety Information
| Hazard Codes | T+;N,N,T+,Xn,F |
| Risk Statements | 26-37-40-41-43-50/53-36-20/21/22-11 |
| Safety Statements | 28-36/37/39-45-60-61-36/37-26-16 |
| RIDADR | 3276 |
| WGK Germany | 3 |
| RTECS | NT2600000 |
| TSCA | TSCA listed |
| HazardClass | 6.1(a) |
| PackingGroup | I |
| HS Code | 29269090 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 2 Inhalation Aquatic Acute 1 Aquatic Chronic 1 Carc. 2 Eye Dam. 1 Skin Sens. 1 STOT SE 3 |
| Hazardous Substances Data | 1897-45-6(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: >10.0 g/kg (Turner) |
| Description | Chlorothalonil is a broad-spectrum organic fungicide mainly used to control fungi that threatens a number of agricultural crops, vegetables, trees, fruits, turf and paints, etc. It can also serves as a wood protectant, pesticide, acaricide, which is effective to kill mildew, bacteria, algae, and insects. Besides, it can commercially act as a preservative additive in several paints, resins, emulsions, coatings and can be used on commercial grasses such as golf courses and lawns. Chlorothalonil was first registered by the EPA in 1966. It is environmentally persistent and binds strongly with soil, whose expected half-life in aerobic soils is one to three months. Chlorothalonil functions by reducing the intracellular glutathione molecules of fungal to alternate its forms which affects the essential enzymatic reactions of fungal, ultimately leading to cell death. |
| uses | Chlorothalonil is a fungicide with a broad spectrum of activity used mainly in agriculture but also on turf, lawns and ornamental plants. It protects plants against a variety of fungal infections such as rusts, downy mildew, leaf spot, scabs, blossom blight and black pod. Crops protected include pome fruit, stone fruit, citrus, currants, cranberries, strawberries, bananas, vines, hops, tomatoes, green vegetables, tobacco, coffee, tea, soya bean, groundnuts, potatoes, onions, cereals and sugar beet. In addition, it is used in wood preservatives, fish net coatings and anti-fouling paints. |
| References | http://www.toxipedia.org/display/toxipedia/Chlorothalonil http://pmep.cce.cornell.edu/profiles/extoxnet/carbaryl-dicrotophos/chlorothalonil-ext.html https://en.wikipedia.org/wiki/Chlorothalonil |
| Description | Chlorothalonil is a pesticide fungicide commonly usedin the cultivation of ornamental plants and flowers,rice, and onions. In banana plantations it is used infumigations by airplanes. It can be used as a preservativeof paints and of woods. Chlorothalonil caninduce contact urticaria, irritant and allergic contactdermatitis, erythema dychromicum perstans orfolliculitis mainly in agricultural workers, in those inwood-related professions or in hortieulturists. |
| Chemical Properties | Chlorothalonil is a combustible, white, odorless, crystalline solid |
| Uses | Chlorothalonil is a non-systemic foliar fungicide with protectiveactivity. It is used to control a broad spectrum of fungal diseases in fruit(pome, stone, citrus, etc.), berries, vegetables, cucurbits, root crops, soyabeans,ornamentals and turf. |
| Uses | Chlorothalonil is a polychlorinated aromatic broad spectrum non-systematic fungicide. Chlorothalonil is used heavily in agriculture field on crops such as peanuts, potatoes and tomatoes. Chlorothalonil is a probable human carcinogen (Group B2) and is highly toxic to fish and aquatic invertabrates. |
| Definition | ChEBI: A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops. |
| General Description | Colorless crystals or granules or light gray powder. Melting point 250-251°C. No odor when pure; technical grade has a slightly pungent odor. A fungicide formulated as water-dispersible granules, wettable powder, or dust. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Chlorothalonil is stable in neutral or acidic aqueous media. May react violently with strong oxidizing acids [Farm Chemicals Handbook]. Incompatible with other oxidizing agents such as peroxides and epoxides. Breaks down slowly in basic aqueous media (half-life 38.1 days at pH 9. [Farm Chemicals Handbook]. |
| Health Hazard | Chlorothalonil is an irritant tothe skin and eyes and has been reported toproduce allergic contact dermatitis in exposedworkers. |
| Fire Hazard | Literature sources indicate that Chlorothalonil is nonflammable. |
| Flammability and Explosibility | Not classified |
| Agricultural Uses | Fungicide: Chlorothalonil is a broad-spectrum fungicide. It is used on vegetables, peanuts, potatoes, small fruits, trees, turf, roses, ornamentals, and other crops. In California, the top crops are tomatoes, onions, celery, and landscaping. It targets fungal blights, needlecasts, and cankers on conifer trees. This is the second most used fungicide in the U.S. It can be found in formulations with many other pesticides |
| Trade name | ATLAS CROPGARD®; BANOL C®; BB CHLOROTHALONIL®; BOMmHgDIER®; BRAVO®; BRAVO® 6 F; BRAVO® 500; BRAVO® 6 F; BRAVO ULTREX®; BRAVO-W-75®; CHILTERN OLE®; CONTACT® 75; DAC® 2787; DACONIL®; DACONIL® 2787 FUNGICIDE; DACONIL® 2787 W; DACONIL® F; DACONIL® M; DACONIL® TURF; DACOSOIL®; DIVA FUNGICIDE®[C]; ECHO®; EXOTHERM®; EXOTHERM TERMIL®; FORTURF®; FUNGINIL®; IMPACT EXCEL®; JUPITAL®; NUOCIDE®; OLE®; PILLARICH®; POWER CHLOROTHALONIL® 50; REPULSE®; RIDOMIL GOLD/BRAVO®; SICLOR®; SIPCAM® UK ROVER 5000; SWEEP®; TER-MIL®; TPN®; TPN (PESTICIDE)®; TRIPART FABER®; TRIPART ULTRAFABER®; TUFFCIDE® |
| Contact allergens | Chlorothalonil is a fungicide widely used in the cultivationof ornamental plants and flowers, rice, andonions. In banana plantations it is used in fumigationsby airplanes. It can be used as a preservative of paintsand woods. It can induce contact urticaria, irritant andallergic contact dermatitis, erythema dyschromicumperstans, or folliculitis mainly in agricultural workers,wood-related professions, or in horticulturists. |
| Pharmacology | Mechanism of action of this fungicide may be attributedto inhibition of physiological activities of fungal cell constituentsby binding reaction. The reaction was observed inbuffer solution to substitute hydroxyethylthio radical(s) of2-mercaptoethanol for chlorine radical(s) on the benzenering of the fungicide molecule preferably at 4-position(i.e., also 6-) followed by other positions (5). Similarreactions in fungal cells were observed between thefungicide and glutathione and high molecular weight cellconstituents having a sulfhydryl group (5,6). The fungicideinhibits activities of thiol-dependent enzymes such asalcohol dehydrogenase, gyceraldehyde-3-phosphate dehydrogenase,and malate dehydrogenase (5,6). Preliminaryaddition of glutathione or dithiothreitol protects the thiolenzymes from inhibition but later addition does not reversethe enzyme inhibition. Chymotrypsin, a non-thiol enzyme,was not inhibited by this fungicide. Binding of the fungicideto the sulfhydryl group of cell constituents appears tobe the primary mode of its action. |
| Safety Profile | Suspected carcinogen with experimental carcinogenic data. Moderately toxic by skin contact and intraperitoneal routes. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and CN-. See also NITRILES. |
| Potential Exposure | Chlorothalonil is a broad spectrum fungicide; used as fungicide in coatings; caulk, wood preservative, and antifouling systems. Therefore, people involved in its manufacture, formulation, and application can be exposed. |
| First aid | If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least2030 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit |
| Carcinogenicity | Chlorothalonil was not mutagenic in avariety of assays, nor did it bind to DNA.3 Thecompound does not appear to have genotoxicpotential and probably exerts its carcinogenicaction in rodents via a nongenotoxic mechanism.3 Rodent models may be a poor predictorof carcinogensis in humans because of speciesdifferences in metabolic pathways leading tocarcinogenesis in the kidney and the lack of acomparable organ (forestomach) in humans. The IARC has determined that there issufficient evidence for carcinogenicity ofchlorothalonil in experimental animals andinadequate evidence in humans. |
| Environmental Fate | Biological. From the first-order biotic and abiotic rate constants of chlorothalonil inestuarine water and sediment/water systems, the estimated biodegradation half-lives were8.1–10 and 1.8–5 days, respectively (Walker et al., 1988). Soil. Metabolites identified in soil were 1,3-dicyano-4-hydroxy-2,5,6-trichlorobenzene,1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene and 1-carbamoyl-3-cyano-4-hydroxy-2,5,6-trichlorobenzene (Rouchaud et al., 1988). The half-life was reported as 4. Groundwater. According to the U.S. EPA (1986) chlorothalonil has a high potentialto leach to groundwater Plant. Degrades in plants to 4-hydroxy-2,5,6-trichloroisophthalonitrile (Hartley andKidd, 1987), 1,3-dicyano-4-hydroxy-2,5,6-trichlorobenzene and 1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene (Rouchaud et al., 1988). No evidence of degradation products werereported in apple foliage 15 days after application. The half-life of chlorothalonil was 4.1days (Gilbert, 1976) |
| Metabolic pathway | By in vitro incubation of 14C-chlorothalonil (CTL) withrat stomach, duodenum, and cecum contents, withdog stomach, duodenum, and colon contents, and withhuman feces and stomach contents, transformation ofCTL mostly occurs in rat cecum contents, dog colon contents, and human feces, in which unchangedCTL accounts for 46.7, 29.7, and 22.6% of appliedradioactivity, respectively. In those incubations,the identified metabolites are 2,5,6-trichloro-4-methylthioisophthalonitrile, 2,5,6-trichloro-4-thioisophthalonitrile, 3-thia-1-cyano-2,5,6-trichloroisoindolinone, 2,5,6-trichloro-4-hydroxyisophthalonitrile, and 2,5,6-trichloroisophthalonitrile. In rats, CTL is transformedto 4,6-bis(N-acetylcystein-S-yl)-2,5-dichloroisophthalonitrile. The photolysis of CTL solutions in alcohols(ethanol and methanol separately) with exposure toUV irradiation yields 4,5,7-trichloro-6-cyano-3-methylbenzo-g -lactone and dichlorobenzo-bis-g -lactonederivatives as major degradation products in ethanol.In methanol, 4,5,7-trichloro-6-cyanobenzo-g -lactone isthe only photoproduct detected. |
| Metabolism | Degradation pathways of chlorothalonil in upland andpaddy soils (7) and by soil bacteria (8) were studied,and most initial products were identified to be theresults of chlorine substitution reactions, by hydrogen(i.e., dechlorination), by hydroxyl, and by methylthiogroups. These reactions took place first at the 4-positionof the ring followed by reactions at other positions asin the reaction with thiol compounds. Paddysoil degraded the fungicide faster than did uplandsoil. Chlorine substitution reaction at 4-position of thefungicide molecule was also reported in benzene solutionunder sunlight, and the phenyl-substituted product wasidentified (9). Similar photolysis was observed inother aromatic hydrocarbon solutions but not in acetone,hexane, and ether solutions. |
| storage | Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Prior to working with chlorothalonil you should be trained on its proper handling andstorage. Store in tightly closed containers in a cool, wellventilated area. Metal containers involving the transfer ofthis chemical should be grounded and bonded. Drums mustbe equipped with self-closing valves, pressure vacuumbungs, and flame arresters. Use only nonsparking tools andequipment, especially when opening and closing containersof this chemical. Sources of ignition, such as smoking andopen flames, are prohibited where this chemical is used,handled, or stored in a manner that could create a potentialfire or explosion hazard. A regulated, marked area shouldbe established where this chemical is handled, used, orstored in compliance with OSHA Standard 1910.1045 |
| Shipping | UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5). UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required |
| Degradation | Chlorothalonil is stable to aqueous hydrolysis at pH values above 7. It ishydrolysed slowly at pH 9 via dechlorination to yield 4-hydroxy-2,5,6-trichloroisothalonitrile (2) and oxidation/hydration of one of the nitrilegroups to yield 3-cyano-2,4,5,6-tetrachlorobenzamide (3) (Szalkowski andStallard, 1977). |
| Toxicity evaluation | Chlorothalonil’s production and use as a broad-spectrum,nonsystemic, protectant pesticide results in its direct release to theenvironment. Its uses as a wood protectant, antimold and antimildewagent, bactericide, microbiocide, algaecide, insecticide,and acaricide are additional routes of release. If released to air,chlorothalonil will exist in both the vapor and particulate phasesin the ambient atmosphere. Vapor-phase chlorothalonil will bedegraded slowly in the atmosphere by reaction withphotochemically produced hydroxyl radicals (reaction half-life～7 years). Direct photolysis may also occur. Chlorothalonil isremoved from the atmosphere by wet and dry deposition. Ifreleased to soil, chlorothalonil is expected to have lowmobility orbe immobile, based on Koc values in the range of 900–7000measured in four soils. Volatilization from moist or dry soilsurfaces is not expected to be important based on a Henry’s Lawconstant of 2.5×10-7 atm-cummol-1. Aerobic biodegradationhalf-lives of chlorothalonil in four different soils ranged from10 to 40 days. If released into water, chlorothalonil is expectedto adsorb to suspended solids and sediment in the water column. |
| Incompatibilities | Contact with strong oxidizers may cause a fire and explosion hazard. Thermal decomposition may include fumes of hydrogen cyanide. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. |
| Waste Disposal | Incineration in a unit operating @ 850C equipped with off-gas scrubbing equipment. |
Chlorothalonil Preparation Products And Raw materials
| Raw materials | Hydrochloric acid-->Ammonia-->Chlorine-->Carbon dioxide-->Activated carbon-->Benzonitrile-->m-Xylene-->Bifenthrin-->1,3-Dicyanobenzene |
| Preparation Products | 2,4,5-Trifluorobenzoic acid |
