テトラクロロイソフタロニトリル 化学特性,用途語,生産方法
外観
白色～うすい黄色粉末～結晶
用途
殺菌剤、防かび剤、防汚剤
主な用途／役割
ニトリル系抗菌剤
説明
Chlorothalonil is a pesticide fungicide commonly used
in the cultivation of ornamental plants and flowers,
rice, and onions. In banana plantations it is used in
fumigations by airplanes. It can be used as a preservative
of paints and of woods. Chlorothalonil can
induce contact urticaria, irritant and allergic contact
dermatitis, erythema dychromicum perstans or
folliculitis mainly in agricultural workers, in those in
wood-related professions or in hortieulturists.
化学的特性
Chlorothalonil is a combustible, white, odorless, crystalline solid
使用
Chlorothalonil is a polychlorinated aromatic broad spectrum non-systematic fungicide. Chlorothalonil is used heavily in agriculture field on crops such as peanuts, potatoes and tomatoes. Chlorothaloni
l is a probable human carcinogen (Group B2) and is highly toxic to fish and aquatic invertabrates.
定義
ChEBI: A dinitrile that is benzene-1,3-dicarbonitrile substituted by four chloro groups. A non-systemic fungicide first introduced in the 1960s, it is used to control a range of diseases in a wide variety of crops.
一般的な説明
Colorless crystals or granules or light gray powder. Melting point 250-251°C. No odor when pure; technical grade has a slightly pungent odor. A fungicide formulated as water-dispersible granules, wettable powder, or dust.
空気と水の反応
Insoluble in water.
反応プロフィール
Chlorothalonil is stable in neutral or acidic aqueous media. May react violently with strong oxidizing acids [Farm Chemicals Handbook]. Incompatible with other oxidizing agents such as peroxides and epoxides. Breaks down slowly in basic aqueous media (half-life 38.1 days at pH 9. [Farm Chemicals Handbook].
健康ハザード
Chlorothalonil is an irritant to
the skin and eyes and has been reported to
produce allergic contact dermatitis in exposed
workers.
火災危険
Literature sources indicate that Chlorothalonil is nonflammable.
农业用途
Fungicide: Chlorothalonil is a broad-spectrum fungicide. It is used on vegetables, peanuts, potatoes, small fruits, trees, turf, roses, ornamentals, and other crops. In California, the top crops are tomatoes, onions, celery, and landscaping. It targets fungal blights, needlecasts, and cankers on conifer
trees. This is the second most used fungicide in the U.S. It can be found in formulations with many other pesticides
製品名
ATLAS CROPGARD®; BANOL C®; BB CHLOROTHALONIL®; BOMmHgDIER®; BRAVO®; BRAVO® 6 F; BRAVO® 500; BRAVO® 6 F; BRAVO ULTREX®; BRAVO-W-75®; CHILTERN OLE®; CONTACT® 75; DAC® 2787; DACONIL®; DACONIL® 2787 FUNGICIDE; DACONIL® 2787 W; DACONIL® F; DACONIL® M; DACONIL® TURF; DACOSOIL®; DIVA FUNGICIDE®[C]; ECHO®; EXOTHERM®; EXOTHERM TERMIL®; FORTURF®; FUNGINIL®; IMPACT EXCEL®; JUPITAL®; NUOCIDE®; OLE®; PILLARICH®; POWER CHLOROTHALONIL® 50; REPULSE®; RIDOMIL GOLD/BRAVO®; SICLOR®; SIPCAM® UK ROVER 5000; SWEEP®; TER-MIL®; TPN®; TPN (PESTICIDE)®; TRIPART FABER®; TRIPART ULTRAFABER®; TUFFCIDE®
接触アレルゲン
Chlorothalonil is a fungicide widely used in the cultivation
of ornamental plants and flowers, rice, and
onions. In banana plantations it is used in fumigations
by airplanes. It can be used as a preservative of paints
and woods. It can induce contact urticaria, irritant and
allergic contact dermatitis, erythema dyschromicum
perstans, or folliculitis mainly in agricultural workers,
wood-related professions, or in horticulturists.
薬理学
Mechanism of action of this fungicide may be attributed
to inhibition of physiological activities of fungal cell constituents
by binding reaction. The reaction was observed in
buffer solution to substitute hydroxyethylthio radical(s) of
2-mercaptoethanol for chlorine radical(s) on the benzene
ring of the fungicide molecule preferably at 4-position
(i.e., also 6-) followed by other positions (5). Similar
reactions in fungal cells were observed between the
fungicide and glutathione and high molecular weight cell
constituents having a sulfhydryl group (5,6). The fungicide
inhibits activities of thiol-dependent enzymes such as
alcohol dehydrogenase, gyceraldehyde-3-phosphate dehydrogenase,
and malate dehydrogenase (5,6). Preliminary
addition of glutathione or dithiothreitol protects the thiol
enzymes from inhibition but later addition does not reverse
the enzyme inhibition. Chymotrypsin, a non-thiol enzyme,
was not inhibited by this fungicide. Binding of the fungicide
to the sulfhydryl group of cell constituents appears to
be the primary mode of its action.
安全性プロファイル
Suspected carcinogen with experimental carcinogenic data. Moderately toxic by skin contact and intraperitoneal routes. Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and CN-. See also NITRILES.
職業ばく露
Chlorothalonil is a broad spectrum fungicide; used as fungicide in coatings; caulk, wood preservative, and antifouling systems. Therefore, people involved in its manufacture, formulation, and application can be exposed.
発がん性
Chlorothalonil was not mutagenic in a
variety of assays, nor did it bind to DNA.3 The
compound does not appear to have genotoxic
potential and probably exerts its carcinogenic
action in rodents via a nongenotoxic mechanism.
3 Rodent models may be a poor predictor
of carcinogensis in humans because of species
differences in metabolic pathways leading to
carcinogenesis in the kidney and the lack of a
comparable organ (forestomach) in humans.
The IARC has determined that there is
sufficient evidence for carcinogenicity of
chlorothalonil in experimental animals and
inadequate evidence in humans.
環境運命予測
Biological. From the first-order biotic and abiotic rate constants of chlorothalonil in
estuarine water and sediment/water systems, the estimated biodegradation half-lives were
8.1–10 and 1.8–5 days, respectively (Walker et al., 1988).
Soil. Metabolites identified in soil were 1,3-dicyano-4-hydroxy-2,5,6-trichlorobenzene,
1,3-dicarbamoyl-2,4,5,6-tetrachlorobenzene and 1-carbamoyl-3-cyano-4-hydroxy-2,5,6-
trichlorobenzene (Rouchaud et al., 1988). The half-life was reported as 4.
Groundwater. According to the U.S. EPA (1986) chlorothalonil has a high potential
to leach to groundwater
Plant. Degrades in plants to 4-hydroxy-2,5,6-trichloroisophthalonitrile (Hartley and
Kidd, 1987), 1,3-dicyano-4-hydroxy-2,5,6-trichlorobenzene and 1,3-dicarbamoyl-2,4,5,6-
tetrachlorobenzene (Rouchaud et al., 1988). No evidence of degradation products were
reported in apple foliage 15 days after application. The half-life of chlorothalonil was 4.1
days (Gilbert, 1976)
代謝経路
By in vitro incubation of 14C-chlorothalonil (CTL) with
rat stomach, duodenum, and cecum contents, with
dog stomach, duodenum, and colon contents, and with
human feces and stomach contents, transformation of
CTL mostly occurs in rat cecum contents, dog colon contents, and human feces, in which unchanged
CTL accounts for 46.7, 29.7, and 22.6% of applied
radioactivity, respectively. In those incubations,
the identified metabolites are 2,5,6-trichloro-4-
methylthioisophthalonitrile, 2,5,6-trichloro-4-
thioisophthalonitrile, 3-thia-1-cyano-2,5,6-
trichloroisoindolinone, 2,5,6-trichloro-4-
hydroxyisophthalonitrile, and 2,5,6-
trichloroisophthalonitrile. In rats, CTL is transformed
to 4,6-bis(N-acetylcystein-S-yl)-2,5-
dichloroisophthalonitrile.
The photolysis of CTL solutions in alcohols
(ethanol and methanol separately) with exposure to
UV irradiation yields 4,5,7-trichloro-6-cyano-3-
methylbenzo-g -lactone and dichlorobenzo-bis-g -lactone
derivatives as major degradation products in ethanol.
In methanol, 4,5,7-trichloro-6-cyanobenzo-g -lactone is
the only photoproduct detected.
代謝
Degradation pathways of chlorothalonil in upland and
paddy soils (7) and by soil bacteria (8) were studied,
and most initial products were identified to be the
results of chlorine substitution reactions, by hydrogen
(i.e., dechlorination), by hydroxyl, and by methylthio
groups. These reactions took place first at the 4-position
of the ring followed by reactions at other positions as
in the reaction with thiol compounds. Paddy
soil degraded the fungicide faster than did upland
soil. Chlorine substitution reaction at 4-position of the
fungicide molecule was also reported in benzene solution
under sunlight, and the phenyl-substituted product was
identified (9). Similar photolysis was observed in
other aromatic hydrocarbon solutions but not in acetone,
hexane, and ether solutions.
輸送方法
UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5). UN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required
不和合性
Contact with strong oxidizers may cause a fire and explosion hazard. Thermal decomposition may include fumes of hydrogen cyanide. 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.
廃棄物の処理
Incineration in a unit operating @ 850C equipped with off-gas scrubbing equipment.
テトラクロロイソフタロニトリル 上流と下流の製品情報
原材料
準備製品