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Name:	2,6-Dichlorobenzonitrile
CAS No:	1194-65-6

PRODUCT DESCRIPTION

【Name】: 2,6-Dichlorobenzonitrile

【CAS Registry number】: 1194-65-6

【Synonyms】: Dichlobenil

【EINECS(EC#)】: 214-787-5

【Molecular Formula】: C7H3Cl2N (Products with the same molecular formula)

【Molecular Weight】: 172.01

【Inchi】: InChI=1/C7H3Cl2N/c8-6-2-1-3-7(9)5(6)4-10/h1-3H

【InChIKey】: YOYAIZYFCNQIRF-UHFFFAOYSA-N

【Canonical SMILES】: C1=CC(=C(C(=C1)Cl)C#N)Cl

【MOL File】
1194-65-6.mol

Chemical and Physical Properties

【Appearance】: white crystalline powder

【Density】: 1.623 g/cm3 (-101 C)

【Melting Point】: 142-147℃

【Boiling Point】: 270-275℃

【Vapour】: 0.00406mmHg at 25°C

【Refractive Index】: 1.583

【Flash Point】: 270°C

【Water】: 25 mg/L (25℃)

【Solubilities】: insoluble

【Color/Form】: White crystalline solid

【Stability】: Stable under normal temperatures and pressures.

【Storage temp】: 0-6°C

【Spectral properties】: Dichlobenil exhibits an absorption maximum at 298 nm (E= 2, 100) in methanol.
Intense mass spectral peaks: 171 m/z (100%), 100 m/z (71%), 173 m/z (69%), 75 m/z (56%)
MASS: 4282 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Intense mass spectral peaks: 136 m/z, 171 m/z

【Computed Properties】: Molecular Weight:172.01142 [g/mol]
Molecular Formula:C₇H₃Cl₂N
XLogP3:2.7
H-Bond Donor:0
H-Bond Acceptor:1
Rotatable Bond Count:0
Exact Mass:170.964255
MonoIsotopic Mass:170.964255
Topological Polar Surface Area:23.8
Heavy Atom Count:10
Formal Charge:0
Complexity:150
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:1
Feature 3D Ring Count:1
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】: Xn:Harmful

【Risk Statements】: R21;R51/53

【Safety Statements 】: S36/37;S61

【HazardClass】: 9

【Hazard Note】: Irritant/Toxic

【PackingGroup 】: III

【Cleanup Methods】: Spills of pesticides at any stage of their storage or handling should be treated with great care. Liquid formulations may be reduced to solid phase by evaporation. Dry sweeping of solids is always hazardous: These should be removed by vacuum cleaning or by dissolving them in water or other solvent in the factory environment. /Pesticides/
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: Pits, ponds, lagoons, soak holes or holding areas used to contain the chemical should be sealed with a impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water.
Environmental considerations: Water spill: If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount.
Personal protection: P2 filter respirator for harmful particles. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place.
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 2769/3077

【Fire Fighting Procedures】: If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)

【Fire Potential】: The formulated product is nonflammable.

【Formulations/Preparations】: USEPA/OPP Pesticide Code 027401; Trade Names: Casoron, Prefix D, Nia 5996, H 133, Du-sprex, Norosac.
59% wettable powder; 75% granules.
Available formulations are 'Casoron' wp, 'Casoron g', containing 45% & 6.75% dichlobenil respectively.
Technical grade dichlobenil is > or =98% pure.
Discontinued Trade names: Barrier; Decabane; Du-Sprex; Dyclomec; Prefix D; Sartax D; Super Granusol D.
Fydulan (granules; combination of dichlobenil and dalapon); Fydulex; Cyclanit (dispersible powder; a combination of dichlobenil and monolinuron).
Technical grade active ingredient: not identified/solid (98 to 99.5%); manufacturing product: not identified/solid (85%), wettable powder (85%); End use product: granular (1 to 10%), liquid-ready to use (0.5%), soluble concentrate/solid (0.5%), wettable powder (0.55 to 85%)
Trade names: ... Decabane, ... Cyclomec, Niagara 5006 ...
Dichlobenil is formulated as 85% ai wettable powder, 1-10% ai granular formulation, 0.5% ai soluble concentrate, and 0.5-85% ai wettable powder

【Reactivities and Incompatibilities】: Dichlobenil as a suspension in water does not deteriorate. It is compatible with most wettable powder herbicides. Mixing with water soluble fertilizers or emulsifiable herbicides is not recommended.

【Other Preventative Measures】: Do not breath dust. Do not allow contact with eyes or skin.
Smoking, eating, drinking /and the use of toilet facilities/ before washing should be absolutely prohibited when any pesticide of moderate or higher toxicity is being handled or used. /Pesticides/
Use with caution. Avoid contamination of feed and feed stuffs. Do not apply during periods of high soil temp without immediate incorporation. On sandy soils lower dosages should be applied.
Prevention /from dichlobenil/ inhalation /use/ ventilation (not if powder), local exhaust, or breathing protection.
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.
Personnel protection: Keep upwind. ... Avoid breathing vapors or dusts. Wash away any material which may have contacted the boyd with copious amounts of water or soap and water.

【Octanol/Water Partition Coefficient】: log Kow = 2.74

【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.
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

Chlorination of 2,6-dichlorotoluene followed by hydrolysis to aldehyde, conversion to oxime & dehydration.
... Method of synthesis involved joint oxidation of 2,6-dichlorotoluene & ammonia with vanadium pentoxide catalyst at 360 deg C. Other methods ... include chlorination of either 2-chloro-6-nitrobenzonitrile or 2-amino-6-chlorobenzonitrile ... .
... Friedel-crafts reaction of 2,6-dichlorobenzamide with mixed chloride salt (NaCl.AlCl3) was reported for synthesis ... .
Made from 2,6-dichlorotoluene via the benzaldehyde ... .
Reaction of 2,6-dichlorobenzaldehyde with hydroxylamine monosulfonate to form anti-2,6-dichlorobenzaldoxime & ... /then/ dehydration ... in boiling acetic anhydride ... .

U.S. Imports

(1977) 3.24X10+5 G (PRINCPL CUSTMS DISTS)
(1982) 7.06X10+10 G (PRINCPL CUSTMS DISTS)

U.S. Production

(1977) Not produced commercially in USA
(1982) Not produced commercially in USA

Consumption Patterns

Essentially 100% as an herbicide

【Usage】: Herbicide (weed growth inhibitor for fruit trees).

Biomedical Effects and Toxicity

【Pharmacological Action】: - Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE.

【Biomedical Effects and Toxicity】: Dogs (Beagles) & rats (Porter strain) did not show species differences in patterns of elimination of metabolites ... Single labeled doses ... were almost entirely eliminated in 4 days. Less than 0.5% ... was present in carcass & viscera after removal of gut ... upwards of 60% appeared in urine.
Roots and cut stems readily absorb dichlobenil from aqueous or nutrient solutions... . Dichlobenil is often absorbed and accumulated in root tissues... before it is translocated upward. ...Under favorable concentration gradients, root-absorbed dichlobenil was excreted back into nutrient solution.
...Radiocarbon from (14)carbon dichlobenil accumulates in parenchyma cells surrounding main veins of bean seedling leaves. Movement and accumulation of radiocarbon in these cells may be result of... transport via intercellular space or across the plasma lemma, adsorption to chloroplasts or other cellular components, and immobilization of conjugated phenolic metabolites as bound "terminal" residues ... (14)carbon balance and vapor-trapping studies have established that substantial amount of translocated radiocarbon is rapidly lost as... dichlobenil by evaporation from aerial portions of intact plants. ...It is also absorbed and translocated by aerial portions of plant. Absorption has been reported... from vapor... and from lanolin paste ... It was translocated in acropetal direction with very limited basipetal movement... .
Studies with (14)carbon dichlobenil showed that more of it was absorbed by rabbits than by rats. ... Unchanged dichlobenil was not found in the urine but was found in the feces.
A single oral dose of (14)Carbon labeled 2,6-dichlorobenzonitrile to rats was almost entirely eliminated in 4 days, 85.8-97.2 of 14C was excreted, 72.3-80.7 in the urine. After oral administration to dogs 86.0-92.5 was excreted, 60.0-70.1 in the urine. [Griffiths MH et al; Biochem J 98 (3): 770-81 (1966)] PubMed Abstract
In guppies and carp exposed to dichlobenil, the metabolite, 3-hydroxy-2,6-dichlorobenzonitrile, was present only in small amounts, 5-10% and 1-2%, respectively.
Single doses of 5 mg/kg (phenyl-U-(14)C) dichlobenil were given to male and female SD rats by either intravenous (iv) or oral administration. Urine and feces were collected at various intervals after dosing. Seven days after iv administration male rats had excreted 70.7% of the dose in the urine and 25.4% of the dose in the feces. Total recovery was 96%. In females, 65.1% and 30.9% of the dose were excreted in the urine and feces, respectively. Total recovery was also 96%. Similar results were obtained 7 days after oral administration. Males excreted 65.1% and 19.2% of the dose in urine and feces, respectively. Total recovery was 84%. Females excreted 64.9% and 20.7% of the dose in urine and feces, respectively. Total recovery was 86%. Thus, the total recoveries following iv dosing were slightly higher than those following oral dosing. The rate of urinary excretion was rapid; excretion was 95% complete in 24 hr. The similarity in total excretion pattern after either an intravenous or oral dose indicates that dichlobenil at the 5 mg/kg dose is readily absorbed from the gastrointestinal tract. In addition, three bile duct-cannulated male rats were dosed orally with 5 mg/kg and bile was collected 2, 5, and 24 hr after administration. For these three rats, 78.9% of the administered dose was recovered in the bile and 19.8% in the urine 24 hr after administration.
... (Phenyl-U-(14)C) dichlobenil in single or multiple doses at dosing levels of 3.75, 30, or 240 mg/kg were given orally. The radiolabeled dichlobenil was given as a single dose on day 1 in one study and on day 1 and day 11 in a multiple-dose study, with rats receiving unlabeled test material on days 2 to 10. Rats receiving a single dose of radiolabeled dichlobenil excreted 55% to 69% of the dose in the urine and 15% to 20% in the feces. Total recoveries at the 2 lower doses were between 89% and 92%. At the highest dose, total recoveries accounted for 77% to 83% of the dose. There were no significant sex-related differences. Similar elimination patterns were noted following the administration of radiolabeled dichlobenil on day 11. Although some saturation kinetics were noted at the high dose, there were no major differences related to sex or dosing regimens. The great similarities in the percentage excretions for the three dosing levels indicate that dichlobenil administered orally up to the high-dose levels was readily absorbed by the rats. Tissue residue levels were dose-dependent. The highest residue levels were in the liver in the rats receiving the highest dose tested.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 49-323 measured in several soils(2), indicates that dichlobenil is expected to have high to moderate mobility in soil(SRC). Volatilization of dichlobenil from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 6.6X10-4 mm Hg(3), and water solubility, 14.6 mg/L(3). Dichlobenil is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). The half-life of dichlobenil in soil is typically 1-6 months depending upon soil type, with 2,6-dichlorobenzamide (which is slowly degraded to 2,6-dichlorobenzoic acid) observed as a major metabolite(3). Field studies using a sandy soil plot and application rates of 8.3 and 16.6 kg/ha indicate that the overall persistence time of dichlobenil is approximately one year(4). An initial half-life of approximately 4 weeks was observed for surface applied dichlobenil, which was primarily due to volatilization losses. Incorporation of the granules into the soil by mechanical tillage, resulted in significantly longer persistence due to a decreased rate of volatilization(4).
TERRESTRIAL FIELD DISSIPATION: Dichlobenil dissipated with a calculated half-life of 241 days from the upper 3 inches of silt loam soil in field plots that were planted to arborvitae in Hillsboro, Oregon. The average dichlobenil concentrations from the deeper soil layers were
IN SOIL, HALF-LIFE ... WAS 28 WK @ 6.7 DEG C (AFTER INITIAL 10 WK LAG PERIOD) & 19 WK @ 26.7 DEG C. ... THE ONLY DETECTABLE METABOLITE WAS 2,6-DICHLOROBENZAMIDE.
KALE PLANTS WERE EXPOSED TO DICHLOBENIL SOLN THROUGH ... SOIL TREATMENT. ... HALF-LIFE OF DICHLOBENIL @ 2.5 MG/POT WAS 44 DAYS; @ 0.5 MG/POT WAS 46 DAYS; & @ 0.25 MG/POT WAS 46 DAYS.
AQUATIC FATE: Based on a classification scheme(1), a Koc value of 114 measured in aquatic sediment(2), indicates that dichlobenil is not expected to adsorb to suspended solids and sediment in the water column(SRC). Volatilization from water surfaces is expected to be an important fate process(3) based upon an estimated Henry's Law constant of 1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 6.6X10-4 mm Hg(4), and water solubility, 14.6 mg/L(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 and 40 days, respectively(SRC). According to a classification scheme(5), BCF values of 10 to 35 measured in fish(2), suggests bioconcentration in aquatic organisms is low to moderate(SRC). A sediment biodegradation rate constant of 0.03 day-1 was calculated for dichlobenil applied in granular form to a NY pond(6). This rate constant corresponds to a degradation half-life of about 23 days(6). Aquatic field dissipation studies suggest that dichlobenil dissipates from the surface of ponds to which it was applied with half-lives of 15-69 days, with much of the loss due to volatilization(2). Dichlobenil does not undergo hydrolysis at pH 5-9(2), but may be susceptible to photolysis in sunlit surface waters, based on aqueous photolysis half-lives of 10.2 days(4) and 15.1 days(2).
AQUATIC FIELD DISSIPATION: Dichlobenil dissipated from pond water with a calculated half-life of 15 days following a surface application (15 lbs ai/A) to a pond located near Bascom, Florida. Average dichlobenil concentrations in water samples taken 1-2 feet from the pond bottom were 0.11 ppm immediately post-treatment, 0.19 ppm at 7 days, 0.093 ppm at 21 days and were not detected by 84 days posttreatment. Dichlobenil was detected to the 6- to 12-inch depth of sediment. The degradate, 2,6-dichlorobenzamide, was not detected in the water or sediment (detection limit is 0.01 ppm). Dichlobenil dissipated from pond water with a calculated half-life of 69 days following a surface application of dichlobenil at 15 lb ai/A to a pond located near Philomath, Oregon. Average dichlobenil concentration in water samples taken 1-2 feet from the pond bottom were
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlobenil, which has a vapor pressure of 6.6X10-4 mm Hg at 20 deg C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dichlobenil is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 94 days(SRC), calculated from its rate constant of 1.7X10-13 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase dichlobenil is removed from the atmosphere by wet and dry deposition. The photolysis half-life for dichlobenil in water (40 deg northern latitude natural sunlight) has been reported as 10.2 days(2); suggesting that direct photolysis in the atmosphere is possible(SRC).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Use and Manufacturing

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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