| Identification | More | [Name]
2,6-Dichlorobenzonitrile | [CAS]
1194-65-6 | [Synonyms]
2,6-DICHLOROBENZONITRILE
AKOS BBS-00004654
BARRIER
CASORON
CASORON(R)
DBN
DICHLOBENIL
DICHLORBENIL
DICLOBENIL
DYCLOMEC
H-133
'LGC' (1113)
NIAGARA 5006
SILBENIL
2,4-Dbn
2,6-Dbn
2,6-Dichlorbenzonitril
2,6-dichloro-benzonitril
2,6-dichlorophenylcyanide
Benzonitrile, 2,6-dichloro- | [EINECS(EC#)]
214-787-5 | [Molecular Formula]
C7H3Cl2N | [MDL Number]
MFCD00001781 | [Molecular Weight]
172.01 | [MOL File]
1194-65-6.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N,T,Xi | [Risk Statements ]
R21:Harmful in contact with skin.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9/PG 3
| [WGK Germany ]
2
| [RTECS ]
DI3500000
| [Hazard Note ]
Irritant/Toxic | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29269090 | [Hazardous Substances Data]
1194-65-6(Hazardous Substances Data) | [Toxicity]
LD50 in rats, mice (mg/kg): 2710, 6800 orally (Bailey, White) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
1,2-Dichlorobenzene-->Dehydrolyzing agent-->2,6-Dichlorotoluene-->2,6-Dichloroaniline-->2,6-Dichlorobenzaldoxime-->2,6-Dichlorobenzal chloride | [Preparation Products]
Chlorfluazuron-->2,6-Difluorobenzonitrile-->Diflubenzuron-->Teflubenzuron-->2,6-BIS(2,2,2-TRIFLUOROETHOXY)BENZONITRILE-->2',6'-Dichloroacetophenone-->2,6-Dichlorobenzaldehyde |
| Hazard Information | Back Directory | [General Description]
DICHLOBENIL(1194-65-6) is a white solid dissolved or suspended in a water-emulsifiable liquid carrier. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Can cause illness by inhalation, skin absorption and/or ingestion. Used as a herbicide. | [Reactivity Profile]
A halogenated nitrile. 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. | [Air & Water Reactions]
Not soluble in water. | [Health Hazard]
SOLID: Harmful if swallowed. | [Fire Hazard]
Not flammable. | [Chemical Properties]
white powder | [Uses]
2,6-dichlorobenzonitrile in which Q-amino-G- chlorobenzonitrile is used as starting material. And it is used for the synthesis of diclofenac sodium oxacillin and guanabenz acetate. | [Uses]
Herbicide. | [Uses]
Soil-applied herbicide used to control many annual and perennial broad-leaved
weeds. | [Definition]
ChEBI: A nitrile that is benzonitrile which is substituted by chlorines at positions 2 and 6. A cellulose synthesis inhibitor, it is used as a pre-emergent and early post-emergent herbicide. | [Synthesis Reference(s)]
Synthetic Communications, 20, p. 2785, 1990 DOI: 10.1080/00397919008051490
Synthesis, p. 943, 1992 DOI: 10.1055/s-1992-26271 | [Flammability and Explosibility]
Nonflammable | [Agricultural Uses]
Herbicide: Dichlobenil is a herbicide used on cranberry bogs,
dichondra, ornamentals, blackberry, raspberry, and blueberry
fields, apple, pear, filbert and cherry orchards,
vineyards, hybrid poplar-cottonwood plantations, and
rights-of-way to control weeds; and sewers to remove
roots. It acts on dandelion, prickly oxtongue (pre-emergence),
and tree roots. Not approved for use in EU countries.
Actively registered in the U.S. | [Trade name]
BARRIER®; BH Prefix D®;
CARSORON®; CASORON® 133; CARSORON® G;
CARSORON® G4; CARSORON® G20-SR; CODE H
133®; DECABANE®; DU-SPREX®; DYCLOMEC®;
FYDULAN; FYDUMAS; FYDUSIT; H 133®; H 1313®;
NIA 5996®; NIAGARA® 5006; NIAGARA 5,996;
NOROSAC®; PREFIX D® | [Environmental Fate]
Biological. A cell suspension of Arthrobacter sp., isolated from a hydrosol, degraded
dichlobenil to 2,6-dichlorobenzamide (71% yield) and several unidentified water soluble
metabolites (Miyazaki et al., 1975). This microorganism was capable of rapidly degrading
dichlobenil in aerobic sediment-water suspensions and in enrichment cultures (Miyazaki
et al., 1975).
Soil. The major soil metabolite is 2,6-dichlorobenzamide which undergoes further
degradation to form 2,6-dichlorobenzoic acid. The estimated half-lives ranged from 1 to
12 months (Hartley and Kidd, 1987). Under field conditions, dichlobenil persists from 2
to 12 months (Ashton and Monaco, 1991). The disappearance of dichlobenil from a
hydrosol and pond water was primarily due to volatilization and biodegradation. The time
required for 50 and 90% dissipation of the herbicide from a hydrosol were approximately
20 and 50 days, respectively (Rice et al., 1974). Dichlobenil has a high vapor pressure
and volatilization should be an important process. Williams and Eagle (1979) found that
the half-life of dichlobenil was 4 weeks in soil 4–8 weeks after application. After 1 year
following application, the half-life increased to 1 year.
Plant. In plants, dichlobenil is transformed into glucose conjugates, insoluble residues
and hydroxy products that are phytotoxic (Ashton and Monaco, 1991). These include three
phytotoxic compounds, namely 2,6-dichlorobenzonitrile, 3-hydroxy-2,6-dichlorobenzonitrile
and 4-hydroxy-2,6-dichlorobenzonitrile (Duke et al., 1991). Massini (1961) provided
some evidence that dichlobenil is metabolized by plants. French dwarf beans, tomatoes,
gherkin and oat plants were all exposed to a saturated atmosphere of dichlobenil at room
temperature for 4 days. Most of the herbicide was absorbed and translocated by the plants
in 3 days. After 6 days of exposure, bean seedlings were analyzed for residues using thinlayer
plate chromatography. In addition to dichlobenil, another compound was found but
it was not 2,6-dichlorobenzoic acid (Massini, 1963).
Surface Water. The time required for 50 and 90% dissipation of the herbicide from
New York pond water was approximately 21 and 60 days, respectively (Rice et al., 1974).
Photolytic. When dichlobenil was irradiated in methanol with a 450-W mercury lamp
and a Corex filter for 8 hours, o-chlorobenzonitrile and benzonitrile formed as the major
and minor products, respectively (Plimmer, 1970).
Chemical/Physical. Dichlobenil is hydrolyzed, especially in the presence of alkali, to
2,6-dichlorobenzamide (Briggs and Dawson, 1970; Worthing and Hance, 1991).
Emits toxic fumes of nitrogen oxides and chlorine when heated to decomposition (Sax
and Lewis, 1987). | [Metabolic pathway]
Twelve metabolites are isolated from either urine or
bile from either rats (11 metabolites) or goats (seven
metabolites) given single oral doses of 14C-labeled
2,6-dichlorobenzonitrile (DCBN). Five of these
metabolites are also excreted in urine from rats dosed
orally with 2,6-dichlorothiobenzamide (DCTBA) which
is an acid amide analog. All metabolites from either DCBN or DCTBA are benzonitriles with the following
ring substituents: Cl2, OH (three isomers); Cl2, (OH)2;
Cl, (OH)2; Cl, OH, SH; Cl, OH, SCH3; SOCH3, OH;
Cl2, S-(N-acetyl)cysteine; Cl, S-(N-acetyl)cysteine; Cl,
OH, S-(N-acetyl)cysteine.
The thiobenzamide moiety of DCTBA is converted
to the nitrile in all extracted urinary metabolites. No
hydrolysis of the nitrile in DCBN to either amide or an
acid is detected. Urine is the major route for excretion;
however, enterohepatic circulation occurs. | [Purification Methods]
Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.] |
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