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Chlorothalonil

Basic information Description References Safety Related Supplier

Chlorothalonil Basic information

Product Name:
Chlorothalonil
CAS:
1897-45-6
MF:
C8Cl4N2
MW:
265.91
EINECS:
217-588-1
Mol File:
1897-45-6.mol
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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)
Flash point:
2 °C
storage temp. 
0-6°C
form 
Powder
Water Solubility 
0.6-1.2 mg l-1 (25 °C)
color 
White
Merck 
14,2166
BRN 
1978326
Exposure limits
An experimental carcinogen.
InChIKey
CRQQGFGUEAVUIL-UHFFFAOYSA-N
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)
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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
HazardClass 
6.1(a)
PackingGroup 
I
HS Code 
29269090
Hazardous Substances Data
1897-45-6(Hazardous Substances Data)
Toxicity
LD50 orally in rats: >10.0 g/kg (Turner)
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Chlorothalonil Usage And Synthesis

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.

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 used in the cultivation of ornamental plants and flowers, rice, and onions. In banana plantations it is used in fumigations by airplanes. It can be used as a preservative of paints and of woods. Chlorothalonil can induce contact urticaria, irritant and allergic contact dermatitis, erythema dychromicum perstans or folliculitis mainly in agricultural workers, in those in wood-related professions or in hortieulturists.

Chemical Properties

White Solid

Chemical Properties

Chlorothalonil is a combustible, white, odorless, crystalline solid

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. Chlorothaloni l is a probable human carcinogen (Group B2) and is highly toxic to fish and aquatic invertabrates.

Uses

Fungicide; bactericide; nematocide

Uses

Fungicide, bactericide, nematocide. Agricultural and horticultural fungicide.

Uses

Chlorothalonil is a non-systemic foliar fungicide with protective activity. 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.

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 to the skin and eyes and has been reported to produce allergic contact dermatitis in exposed workers.

Fire Hazard

Literature sources indicate that Chlorothalonil is nonflammable.

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 cultivation of ornamental plants and flowers, rice, and onions. In banana plantations it is used in fumigations by airplanes. It can be used as a preservative of paints and woods. It can induce contact urticaria, irritant and allergic contact dermatitis, erythema dyschromicum perstans, or folliculitis mainly in agricultural workers, wood-related professions, or in horticulturists.

Pharmacology

Mechanism of action of this fungicide may be attributed to inhibition of physiological activities of fungal cell constituents by binding reaction. The reaction was observed in buffer solution to substitute hydroxyethylthio radical(s) of 2-mercaptoethanol for chlorine radical(s) on the benzene ring of the fungicide molecule preferably at 4-position (i.e., also 6-) followed by other positions (5). Similar reactions in fungal cells were observed between the fungicide and glutathione and high molecular weight cell constituents having a sulfhydryl group (5,6). The fungicide inhibits activities of thiol-dependent enzymes such as alcohol dehydrogenase, gyceraldehyde-3-phosphate dehydrogenase, and malate dehydrogenase (5,6). Preliminary addition of glutathione or dithiothreitol protects the thiol enzymes from inhibition but later addition does not reverse the enzyme inhibition. Chymotrypsin, a non-thiol enzyme, was not inhibited by this fungicide. Binding of the fungicide to the sulfhydryl group of cell constituents appears to be 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.

Carcinogenicity

Chlorothalonil was not mutagenic in a variety of assays, nor did it bind to DNA.3 The compound does not appear to have genotoxic potential and probably exerts its carcinogenic action in rodents via a nongenotoxic mechanism. 3 Rodent models may be a poor predictor of carcinogensis in humans because of species differences in metabolic pathways leading to carcinogenesis in the kidney and the lack of a comparable organ (forestomach) in humans.
The IARC has determined that there is sufficient evidence for carcinogenicity of chlorothalonil in experimental animals and inadequate evidence in humans.

Environmental Fate

Biological. From the first-order biotic and abiotic rate constants of chlorothalonil in estuarine water and sediment/water systems, the estimated biodegradation half-lives were 8.1–10 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 potential to leach to groundwater
Plant. Degrades in plants to 4-hydroxy-2,5,6-trichloroisophthalonitrile (Hartley and Kidd, 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 were reported in apple foliage 15 days after application. The half-life of chlorothalonil was 4.1 days (Gilbert, 1976)

Metabolic pathway

By in vitro incubation of 14C-chlorothalonil (CTL) with rat stomach, duodenum, and cecum contents, with dog stomach, duodenum, and colon contents, and with human feces and stomach contents, transformation of CTL mostly occurs in rat cecum contents, dog colon contents, and human feces, in which unchanged CTL accounts for 46.7, 29.7, and 22.6% of applied radioactivity, 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 transformed to 4,6-bis(N-acetylcystein-S-yl)-2,5- dichloroisophthalonitrile.
The photolysis of CTL solutions in alcohols (ethanol and methanol separately) with exposure to UV irradiation yields 4,5,7-trichloro-6-cyano-3- methylbenzo-g -lactone and dichlorobenzo-bis-g -lactone derivatives as major degradation products in ethanol. In methanol, 4,5,7-trichloro-6-cyanobenzo-g -lactone is the only photoproduct detected.

Metabolism

Degradation pathways of chlorothalonil in upland and paddy soils (7) and by soil bacteria (8) were studied, and most initial products were identified to be the results of chlorine substitution reactions, by hydrogen (i.e., dechlorination), by hydroxyl, and by methylthio groups. These reactions took place first at the 4-position of the ring followed by reactions at other positions as in the reaction with thiol compounds. Paddy soil degraded the fungicide faster than did upland soil. Chlorine substitution reaction at 4-position of the fungicide molecule was also reported in benzene solution under sunlight, and the phenyl-substituted product was identified (9). Similar photolysis was observed in other aromatic hydrocarbon solutions but not in acetone, hexane, and ether solutions.

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 is hydrolysed slowly at pH 9 via dechlorination to yield 4-hydroxy-2,5,6- trichloroisothalonitrile (2) and oxidation/hydration of one of the nitrile groups to yield 3-cyano-2,4,5,6-tetrachlorobenzamide (3) (Szalkowski and Stallard, 1977).

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

Preparation Products

Raw materials

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ChlorothalonilSupplierMore

Bailing Agrochemical Co., Ltd. Gold
Tel:
0510-86822183
Email:
info@bailingcn.com
Products Intro:
Product Name:CHLOROTHALONIL
CAS:1897-45-6
Shandong XiYa Chemical Industry Co., Ltd Gold
Tel:
400-990-3999
Email:
3007715519@qq.com;3007715519@qq.com
Products Intro:
CAS:1897-45-6
Purity:98% Package:585RMB/500g
Wuhai Shuou Technology Co., Ltd. Gold
Tel:
17792809151
Email:
2355916837@ycphar.com;2355916837@ycphar.com
Products Intro:
CAS:1897-45-6
Purity:75% Package:50.00RMB/1kg
J & K SCIENTIFIC LTD.
Tel:
400-666-7788 010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Products Intro:
Product Name:Chlorothalonil, 98%
CAS:1897-45-6
Purity:98% Package:25G;5G
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel:
400-660-8290 21-61259100-
Email:
sh@meryer.com
Products Intro:
Product Name:Tetrachloroisophthalonitrile
CAS:1897-45-6
Purity:95% Remarks:AAM148032
Basic information Description References Safety Related Supplier