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Chlorothalonil

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Name

Chlorothalonil

EINECS 217-588-1
CAS No. 1897-45-6 Density 1.71g/cm3
PSA 47.58000 LogP 4.04356
Solubility 0.6-1.2 mg l-1 (25 °C) Melting Point 250-251oC
Formula C8Cl4N2 Boiling Point 350.5 °C at 760 mmHg
Molecular Weight 265.913 Flash Point 153.8 °C
Transport Information UN 2811 Appearance White crystal
Safety 28-36/37/39-45-60-61-36/37-26 Risk Codes 26-37-40-41-43-50/53-36-20/21/22-11
Molecular Structure Molecular Structure of 1897-45-6 (Chlorothalonil) Hazard Symbols VeryT+,DangerousN,HarmfulXn,FlammableF
Synonyms

Kabiguard 164SA;Nopcocide N 96;Nopcocide 54DB;Vanox;Bravo;Sweep;Dacosoil;Nopcocide;Bravo Ultrex;Termil;Daconil;Nuocide 960;Clortosip;Kavach;Bravo 6F;Thalonil;TPN (pesticide);Daconil M;1,3-Benzenedicarbonitrile,2,4,5,6-tetrachloro-;Daconil 2787;NexGen;Nopcocide N 54D;2,4,5,6-tetrachlorobenzene-1,3-dicarbonitrile;Chlorothalonil (Shandong dacheng pesticide co., ltd);

Article Data 22

Chlorothalonil Synthetic route

1897-45-6

chlorothalonil

7003-32-9

2-METHYLCYCLOHEXYLAMINE

2,4,5-trichloro-6-((2R)-2-methylcyclohexylamino)isophthalonitrile

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 0.25h;98%
1897-45-6

chlorothalonil

3886-69-9

(R)-1-phenyl-ethyl-amine

4-N-((R)-1'-phenylethylamino)-2,5,6-trichloro-1,3-dicyanobenzene

Conditions
ConditionsYield
at 100℃;97%
1897-45-6

chlorothalonil

6321-23-9

4-methylcyclohexylamine

2,4,5-trichloro-6-((4-methylcyclohexyl)amine)isophthalonitrile

Conditions
ConditionsYield
In 1,4-dioxane at 20℃; for 0.25h;97%
1897-45-6

chlorothalonil

3886-69-9

(R)-1-phenyl-ethyl-amine

4,6-di-N-((R)-1'-phenylethylamino)-2,5-dichloro-1,3-dicyanobenzene

Conditions
ConditionsYield
In methanol at 100℃; for 24h;96%
1897-45-6

chlorothalonil

62-53-3

aniline

1142208-21-6

C14H6Cl3N3

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry;95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;78%
With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 5h;
1897-45-6

chlorothalonil

21418-71-3

ethyl 2-(imidazolidin-2-ylidene)acetate

1146217-01-7

C15H11Cl3N4O2

Conditions
ConditionsYield
at 120℃; for 0.2h; Neat (no solvent); Microwave irradiation; regiospecific reaction;93%
at 20 - 120℃; Neat (no solvent); Microwave irradiation; Combinatorial reaction / High throughput screening (HTS);
1897-45-6

chlorothalonil

104-94-9

4-methoxy-aniline

1142208-32-9

C15H8Cl3N3O

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry;93%
91-21-4

1,2,3,4-tetrahydroisoquinoline

1897-45-6

chlorothalonil

2,5,6-trichloro-6-(3,4-quinolin-2 (1H)-yl)isophthalonitrile

Conditions
ConditionsYield
In 1,4-dioxane at 30℃; for 0.166667h;93%
1897-45-6

chlorothalonil

122-39-4

diphenylamine

5-chloro-2,4,6-tris(diphenylamino)isophthalonitrile

Conditions
ConditionsYield
Stage #1: diphenylamine With sodium hydride In tetrahydrofuran at 50℃; for 0.5h; Schlenk technique; Inert atmosphere;
Stage #2: chlorothalonil In tetrahydrofuran at 20℃; for 24h; Schlenk technique; Inert atmosphere;
93%
1897-45-6

chlorothalonil

3886-69-9

(R)-1-phenyl-ethyl-amine

2,4,6-tri-N-((R)-1'-phenylethylamino)-5-chloro-1,3-dicyanobenzene

Conditions
ConditionsYield
at 150℃; for 20h;92%

Chlorothalonil History

CHLOROTHALONIL  was first registered for use in the US in 1966. In 1997, the most recent year for which data is available, it was the third most used fungicide in the US, behind only sulfur and copper, with some 12 million lbs used in agricultural alone that year.Including non-agricultural uses, the EPA estimates that on average almost 15 million lbs were used in annually from 1990-1996.

Chlorothalonil Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 30 ,1983,p. 319.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-41 ,1978. . Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Chlorothalonil Standards and Recommendations

DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans

Chlorothalonil Specification

The IUPAC name of Chlorothalonil is 2,4,5,6-tetrachlorobenzene-1,3-dicarbonitrile. With the CAS registry number 1897-45-6, it is also named as 1,3-Dicyanotetrachlorobenzene. The product's categories are organics; aromatics pesticides & metabolites; endocrine disruptors (draft); EPA; fungicides; pesticides. It is white crystal with no odor when pure; technical grade has a slightly pungent odor. It is stable in neutral or acidic aqueous media and may react violently with strong oxidizing acids. Additionlly, this chemical should be sealed in the container and stored at the temperature of 0-6 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.88; (4)ACD/LogD (pH 7.4): 2.88; (5)ACD/BCF (pH 5.5): 90.2; (6)ACD/BCF (pH 7.4): 90.2; (7)ACD/KOC (pH 5.5): 873.26; (8)ACD/KOC (pH 7.4): 873.26; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.632; (13)Molar Refractivity: 55.19 cm3; (14)Molar Volume: 154.6 cm3; (15)Polarizability: 21.88×10-24 cm3; (16)Surface Tension: 71.2 dyne/cm; (17)Enthalpy of Vaporization: 59.52 kJ/mol; (18)Vapour Pressure: 4.36E-05 mmHg at 25°C; (19)Exact Mass: 265.878609; (20)MonoIsotopic Mass: 263.881559; (21)Topological Polar Surface Area: 47.6; (22)Heavy Atom Count: 14; (23)Complexity: 284.

Preparation of Chlorothalonil: It can be obtained by the direct chlorination of isophthalonitrile or by treating tetrachloroisophthaloyl amide with phosphoryl chloride.

Uses of Chlorothalonil: It is a polychlorinated aromatic mainly used as a broad spectrum, non-systemic fungicide, with other uses as a wood protectant, pesticide, acaricide, and to control mold, mildew, bacteria, algae. In addition, it can react with methanol to get 1,3-dicyano-4-methoxy-2,5,6-trichlorobenzene. This reaction needs reagent water and KOH by heating. The reaction time is 1 hours. The yield is 45%.

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and harmful by inhalation, in contact with skin and if swallowed. In addition, it is irritating to eyes and respiratory system. Chlorothalonil is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) This material and its container must be disposed of as hazardous waste. And people should avoid release to the environment.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1c(C#N)c(Cl)c(C#N)c(Cl)c1Cl
2. InChI:InChI=1/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A090, Pg. 1984,
mouse LD50 intraperitoneal 2500ug/kg (2.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Industrial Health. Vol. 4, Pg. 11, 1966.
mouse LD50 oral 3700mg/kg (3700mg/kg)   Hokkaidoritsu Eisei Kenkyushoho. Report of the Hokkaido Institute of Public Health. Vol. 30, Pg. 53, 1980.
rabbit LD50 skin > 10gm/kg (10000mg/kg)   Pesticide Manual. Vol. 9, Pg. 159, 1991.
rat LC50 inhalation 310mg/m3/1H (310mg/m3)   Farm Chemicals Handbook. Vol. -, Pg. C72, 1991.
rat LD50 oral 10gm/kg (10000mg/kg)   "Agricultural Chemicals," Thomson, W.T., 4 vols., Fresno, CA, Thomson Publications, 1976/77 revisionVol. 4, Pg. 75, 1976/1977.
rat LD50 skin > 2500mg/kg (2500mg/kg)   Fundamental and Applied Toxicology. Vol. 7, Pg. 299, 1986.

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