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外観
白色〜ほとんど白色, 結晶〜粉末
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溶解性
水に不溶 (18mg/l at 20℃)。アセトン, ジオキサン, キシレン : 50g/l (8℃) ; ジクロロメタン100g/l (20℃)。非極性溶媒にほとんど溶けない。アセトンにやや溶けやすく、水にほとんど溶けない。
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農薬用途
除草剤
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化学的特性
2,6-Dichlorobenzonitrile [1194-65-6], 1- cyano-2,6-dichlorobenzene, Mr 172.02, mp 144.5 –146.5 ℃, is a colorless, crystalline substance. Its solubility in water is 10 ppm at 25℃. 2,6-Dichlorobenzonitrile is produced industrially by the ammoxidation of 2,6-dichlorotoluene. In addition the nitrile is obtained by oxidation or side-chain-chlorination of 2,6-dichlorotoluene via 2,6-dichlorobenzoic acid and 2,6-dichlorobenzaldehyde, respectively. 2,6-Dichlorobenzonitrile shows herbicidal activity (Casoron, Duphar) and is used in fruit and vine cultivation. It is also used as an intermediate in the production of 2,6-difluorobenzonitrile and of 2,6-dichlorothiobenzamide (Prefix, Shell) which shows herbicidal activity.
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使用
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.
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定義
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.
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一般的な説明
2,6-Dichlorobenzonitrile 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.
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空気と水の反応
Not soluble in water.
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反応プロフィール
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.
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健康ハザード
SOLID: Harmful if swallowed.
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火災危険
Not flammable.
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农业用途
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.
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製品名
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®
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代謝経路
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.
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純化方法
Crystallise the nitrile from acetone. [Beilstein 9 IV 1006.]
