Related Searches: chlorothalonil

chlorothalonil(CAS No. 1897-45-6)

chlorothalonil C8Cl4N2 (cas 1897-45-6) Molecular Structure

1897-45-6 Structure

Identification and Related Records

【Name】
chlorothalonil
【CAS Registry number】
1897-45-6
【Synonyms】
Tetrachloro isophthalo nitrile
Chlorothalonil suspensoid
Chlorothalonil fumigant
Tetrachloroisophthalodinitrile
【EINECS(EC#)】
217-588-1
【Molecular Formula】
C8Cl4N2 (Products with the same molecular formula)
【Molecular Weight】
265.91
【Inchi】
InChI=1/C8Cl4N2/c9-5-3(1-13)6(10)8(12)7(11)4(5)2-14
【InChIKey】
CRQQGFGUEAVUIL-UHFFFAOYSA-N
【Canonical SMILES】
C(#N)C1=C(C(=C(C(=C1Cl)Cl)Cl)C#N)Cl
【MOL File】
1897-45-6.mol

Chemical and Physical Properties

【Appearance】
white crystalline powder
【Density】
1.71g/cm3
【Melting Point】
250 - 251 C
【Boiling Point】
350 C
【Vapour】
4.36E-05mmHg at 25°C
【Refractive Index】
1.632
【Flash Point】
not considered as a fire hazard
【Solubilities】
poorly soluble SOLVENT
【Color/Form】
WHITE CRYSTALLINE SOLID
Colorless crystals
【Storage temp】
0-6°C
【Spectral properties】
Intense mass spectral peaks: 266 m/z (100%), 264 m/z (85%), 268 m/z (52%), 109 m/z (30%)
MASS: 53897 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
【Computed Properties】
Molecular Weight:265.911 [g/mol]
Molecular Formula:C8Cl4N2
XLogP3:2.9
H-Bond Donor:0
H-Bond Acceptor:2
Rotatable Bond Count:0
Exact Mass:265.878609
MonoIsotopic Mass:263.881559
Topological Polar Surface Area:47.6
Heavy Atom Count:14
Formal Charge:0
Complexity:284
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
T+:Verytoxic;N:Dangerousfortheenvironment;
【Risk Statements】
R26;R37;R40;R41;R43;R50/53
【Safety Statements 】
S28;S36/37/39;S45;S60;S61
【HazardClass】
6.1(a)
【PackingGroup 】
I
【Skin, Eye, and Respiratory Irritations】
Chlorothalonil has caused irritation of the skin and mucous membranes of the eye and respiratory tract on contact.
【Cleanup Methods】
Solid spillage should be picked up with an industrial vacuum cleaner and disposed of in accordance with local regulations.
If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.
After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
【Transport】
UN 2811
【Fire Fighting Procedures】
/To fight fire use/ carbon dioxide, foam, dry chemical or water.
【Fire Potential】
Chlorothalonil is non-flammable and non-explosive.
【Formulations/Preparations】
Wettable powder (75%); flowable (54%, 6 lb/US gal); thermal dust (20% & 90%)
Techical product is about 97% pure.
Bravo W-75, Daconil 2787 W-75 Fungicide, wettable powder (750 g ai/kg)
Bravo 500, Daconil Flowable, Faber ..., Repulse ..., suspension concentrate (500 g/l).
Exotherm Termil, for sublimation in glasshouses.
Trade names: Agronil; Aminil; Ancogard; Banko; Barrachlor; Bronco; Butik; Celeste; Centauro; Chloronil; Chlorosul; Chlorothate; Clorval; Taloberg; Control; Daylin; Equus; Quali-Pro; Fertilonil; Funginil; Gyunzerotan; Hektanil; Karisma; Maconil; Oranil 75; Rothalonil; Rumble; Taloflow; Talone; Talonil; Thalonex; Wopro-chlorothalonil
Trade names: Bravo, Daconil, Tuffcide, Acticide
Flowable, water dispersible granule, wettable powder, exothermic dust.
Discontinued Trade names: Antoleen; Arbitre; Bravo C/M; Bravo Moncut; Bravocarb; Chlorochem; Corbel CL; Corbel Star; Corbel Triple; Dacobre; Ensign; Evade; Flouronil; Reach; Terranil; Terranil Cu; Thaional; Trenetal
Faber
Repulse
Daconil M
DACONIL 2787
DACONIL 2787 W75
Daconil Flowable
Daconil 2787 flowable fungicide
Daconil 2787 W-75 Fungicide
Dacosoil
Nopcocide
Nopcocide N-96
Nopcocide N40D & N96
EXOTHERM
FORTURF
SWEEP
End-use products: With single active ingredient: Dust: 5.0 to 98%; Emulsifiable concentrate: 12.5 to 54%; Flowable concentrate: 11.24 to 54%; Granular: 5.0 to 11.25%; Impregnated material: 20.0%; Liquid-ready to use: 0.087 to 98%; Soluble concentrate: 12.5% to 54%; Dry flowable (water dispersible granules): 40.4 to 90.0%; Wettable powder: 50 to 75.0%.
End-use products: With multiple active ingredients (chlorothalonil and at least one other ai): Dust: 5.0% + 1 ai; Emulsifiable concentrate: 3.75 to 20.0% + 1 ai; Flowable Concentrate: 14.7 to 40.0% + 1 ai; Liquid-ready to use: 0.7% + 1 ai, 11.0% + 2 ai's; Dry flowable (water dispersible granules): 50.0% + 1 ai, 27.0% + 2 ai's; Wettable Powder: 6.0 to 72.0% + 1 ai.
Technical grade 96-98%
Emulsifiable concentrate: 12.5 to 54%; Flowable concentrate: 11.24 to 54%; Granular: 5.0 to 11.25%; Impregnated material: 20%; Liquid-ready to use: 0.087 to 98%; Soluble concentrate 12.5 to 54%; Dry flowable (water dispersible granules): 40.4 to 90.0%; Wettable powder: 50 to 75.0%
【Reactivities and Incompatibilities】
Not compatible with oils.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Avoid contact with skin and eyes.
Prevent dispersion of dust! Avoid all contact! Avoid exposure of adolescents and children!
Do not eat, drink, or smoke during work. Wash hands before eating.
Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.
Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.
Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.
Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
【Protective Equipment and Clothing】
Chemical-resistant gloves. Long-sleeved shirt and long pants. Protective eyewear. Shoes plus socks.
/Wear/ safety /glasses/ or eye protection in combination with breathing protection if powder.
【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.

【Octanol/Water Partition Coefficient】
log Kow= 3.05
【Report】

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.

【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Chlorothalonil can be incinerated in a unit operating @ 850 deg C equipped with off-gas scrubbing equipment. Recommendable method: Incineration.
Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.
Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Reaction of tetrachloroisophthaloyl chloride and ammonia, followed by reaction with a dehydrating agent such as phosphorus pentoxide.
Chlorination of isophthalonitrile.
U.S. Imports

(1976) 1.71X10+9 G (PRINCPL CUSTMS DISTS)
U.S. Production

(1975) 1.6X10+9 G (CONSUMPTION)
(1976) PROBABLY GREATER THAN 2.27X10+6 G
Consumption Patterns

FUNGICIDE, OF WHICH APPROXIMATELY 63% IS USED ON PEANUTS, 17% ON VEGETABLE CROPS OTHER THAN POTATOES, 9% IN PAINTS, 6% ON POTATOES, & 6% ON LAWNS & TURF (1975)
Predominant uses of chlorothalonil are on peanuts (about 34% of total chlorothalonil used in the US), potatoes (about 12%), tomatoes (about 7%), paint (about 13%), and golf courses (about 10%). Other important sites include lawns, and cucurbits.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
- Agents destructive to snails and other mollusks.
【Biomedical Effects and Toxicity】
Following administration of 1 mg/kg body weight (14)C chlorothalonil to male Sprague-Dawley rats by endotracheal instillation, gavage or dermal application, less than 6% of the administered dose was recovered in the blood or urine within 48 hr after dosing.
The average bioconcentration factors in whole body of willow shiner (Gnathopogon caerulescens) were 18 for chlorothalonil. The average bioconcentration values in whole body of carp (Cyprinus carpio L.) were 25 for chlorothalonil. The excretion rate constants (k) from whole body of willow shiner were 0.04 hr-1 for chlorothalonil.
In rats, given a single, oral low dose (1.5mg/kg) of chlorothalonil, around 20-22% of the absorbed dose is excreted in bile and around 10% in urine. At higher dose (200 mg/kg) a considerably lower proportion (8%) of the absorbed dose is excreted in bile, indicating that this is a saturable process. These data indicate that overall absorption from the GI tract is in the order of 30-32% of the administered dose. The majority ... is excreted in feces with at least 80% of administered dose excreted by this route within 96 hr. Approximately 90% of the administered dose was excreted within 34-48 hr although excretion was less rapid at doses of 50 mg/kg and above. Highest tissue concentrations were observed in the kidney, approximately 0.1% of the dose. A similar metabolic profile was seen on repeated dosing and there was no evidence of bioaccumulation.
... Data for the monkey show that, following a single oral dose of 50 mg/kg, 1.8-4.15% of the dose appeared in urine with very low levels of thiol-derived metabolites appearing in urine. Fecal excretion predominated with around 92% of the dose eliminated via this route over 96 hr. Absorption and excretion were rapid and there was no evidence of bioaccumulation.
Low levels of /orally administered chlorothalonil to mouse/ were found in the tissues and urinary excretion indicated that at least 10% of the dose was absorbed with the majority (70-80%) of the dose excreted in feces.
...Four monkeys were treated dermally with 5 mg/kg body weight of 14C-chlorothalonil under a non-occlusive patch. After 48 hr the patch was taken off and the skin was washed. About 90% of the dose was recovered from the surface and about 2.26% was completely absorbed through the skin. The urine contained 1% of the dose, but methylated mono-, di- and trithiols were not detectable in the urine.
Oral administration of 14C-chlorothalonil to four male Chinese rhesus monkeys showed fecal elimination to be the main route of excretion, 52 to 92% of the dose (50 mg/kg) being excreted in 96 hr. Urinary excretion amounted to 1.8 to 4.1% of the dose. Most of the radiolabel was eliminated in the first 48 hr.
The mean absorption rate /of human abdominal epidermis/ observed ... over a 48 to 55 hr exposure interval was 0.034 +/- 0.020 ug/cm2/hr, equating to 0.085% of the applied dose. No radiolabel /of chlorothalonil/ was detected in the receptor chamber fluid until 48 hr after application ...
Uniformly-labeled chlorothalonil was administered into the duodena of Sprague-Dawley rats. Bile was collected via cannula. About 1 to 6% of administered label was excreted in bile. Bile collected during the first 6 hr after dosing was administered to recipient rats. About 19% of this label was excreted by the recipient rats within 24 hr. This suggests significant enterohepatic recirculation.
Three male beagles were administered nominal doses of 50 mg/kg 14C-Chlorothalonil in single gavage administrations. Urine was collected for up to 24 hr by catheters (inserted into the bladders) to eliminate contamination by feces. Urine and feces were collected for a subsequent period (total of 8 days) with catheters removed. Total urinary excretion was estimated to be 0.7 to 1.9% of estimated actual dose: most of this was collected during the first 24 hr. Fecal elimination was estimated to be 83 to 99% of estimated actual dose. Analyses of urine for mono-, di-, and tri-thiols did not detect any of these metabolites.
In a dermal absorption study, 1% 14C chlorothalonil in latex base paint or in alkyd covering stain (0.1 ug/sq cm) was applied to the back of male rats for periods of 8 hours (washed and terminated), 24 hours (washed and terminated) and 24 hours (washed and maintained for an additional 24 hours). For the paint, total recovery was 99-105% with 97-102% being in skin washes, 0.64-1.62% in skin and 0.58-0.99% absorbed (urine, feces, cage wash, blood and carcass). For the stain, total recovery was 89-96%, with 84-95% being in skin washes, 0.56- 1.52% in skin and 0.78-2.97% absorbed.
Distribution of radioactivity was ...studied after repeated oral administration of 14C-chlorothalonil to male rats. Five doses were given at 24 hr intervals at concentrations of 1.5, 5, 50 or 160 mg/kg. The rats were killed 2, 9, 24, 96 and 168 hr after the last dose. The distribution of activity showed a similar profile to that after single dosing, i.e. the highest concentrations occurred in kidneys, followed by liver and blood, at all doses and times. At all dose levels, the concentrations peaked 2 hr after the last dose. The percentage of the dose found in the kidney at this time was 0.28% and 0.20% at the 1.5 and 5 mg/kg dose levels, which was significantly higher than that found at the higher doses (about 0.09%). At dose levels up to 50 mg/kg there was significant depletion of radioactivity from the blood during the 24 hr between doses. In the kidney there was a trend to slower overall depletion with increase in dose.
The fate of orally administered 14C-chlorothalonil (purity 99.7%) at three dose levels (5, 50 and 200 mg/kg) was investigated in Sprague-Dawley rats to determine the effects of increasing doses of the test material. Four animals of each sex at each dose level were killed 2, 9, 24, 96 and 168 hr after dosing and urine, feces and selected tissues were assayed for radioactivity. The average recovery of the radiolabel at each of the dose levels was approximately 89% for males and 96% for females. The major route of elimination was via the feces (83-87%) and was essentially complete by 48 hr in low-dose females and low/mid-dose males, and by 72 hr in the mid/high-dose females and high-dose males. A delay in stomach-emptying time was observed for mid- and high-dose males and females. Urinary excretion was 92-93% complete for low-dose rats within 24 hr, mid-dose rats within 48 hr, and 95% complete for high-dose rats within 72 hr. Urinary excretion of the radiolabel at the three dose levels was 5-7% of the administered dose in males and 5-11.5% in females. Urinary excretion was essentially saturated as the dose level increased. The highest concentrations of radiolabelled material in non-gastrointestinal tissues were found in the kidney, being approximately 0.7% of the dose per gram of kidney for males and 0.4% in females at peak concentration (2 hr) for the 5 mg/kg dose level. Kidney concentrations were greatest at 2, 9 and 24 hr for the low, mid and high doses, respectively.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 900 to 7,000(2), indicate that chlorothalonil is expected to have low mobility or be immobile in soil(SRC). Volatilization of chlorothalonil from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.5X10-7 atm-cu m/mole(3). Chlorothalonil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 5.7X10-7 mm Hg(3). Aerobic biodegradation half-lives of chlorothalonil in four different soils ranged from 10 to 40 days(2).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 900 to 7,000(2), indicate that chlorothalonil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.5X10-7 atm-cu m/mole(4). According to a classification scheme(5), BCF values of 9.4 to 264 measured in fish(2), suggest bioconcentration in aquatic organisms can be low to high(SRC). Chlorothalonil is resistant to hydrolysis at pH 5 and 7; however, chlorothalonil hydrolyzed to 2,5,6-trichloro-4-hydroxyisophtalonitrile and 3-cyano-2,4,5,6-tetrachlorobenzamide at pH 9 with a half-life of 38.1 days(6). Photolysis in sunlit surface waters may occur based on an aqueous photolysis half-life of 65 days(2). Chlorothalonil degrades under aerobic and anaerobic aquatic conditions. Anaerobic half-lives of chlorothalonil in two different flooded soils were in the range of 5 to 15 days(2). Aerobic aquatic half-lives of chlorothalonil in marine water were reported as 8.1 and 8.8 days(7).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorothalonil, which has a vapor pressure of 5.7X10-7 mm Hg at 25 deg C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorothalonil is degraded slowly in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 7 years(SRC), calculated from its rate constant of 6.2X10-15 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase chlorothalonil may be removed from the air by wet and dry deposition(SRC). Chlorothalonil has been shown to undergo direct photolysis in aqueous solutions with a half-life of 65 days(4), which indicates that direct photolysis in the atmosphere may be possible(SRC).

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