| | Dicofol Basic information |
| Product Name: | Dicofol | | Synonyms: | 2,2,2-Trichloor-1,1-bis(4-chloor fenyl)-ethanol;2,2,2-trichloor-1,1-bis(4-chloorfenyl)-ethanol;2,2,2-Trichlor-1,1-bis(4-chlor-phenyl)-aethanol;2,2,2-trichloro-1,1-bis(4-chlorophenyl)-ethanol(french);2,2,2-Trichloro-1,1-bis(4-cloro-fenil)-etanolo;2,2,2-trichloro-1,1-bis(p-chlorophenyl)-ethano;2,2,2-trichloro-1,1-bis(p-chlorophenyl)ethanol;2,2,2-trichloro-1,1-di-(4-chlorophenyl)ethanol | | CAS: | 115-32-2 | | MF: | C14H9Cl5O | | MW: | 370.49 | | EINECS: | 204-082-0 | | Product Categories: | 2000/60/EC;Alphabetic;AcaricidesPesticides&Metabolites;Analytical Standards;European Community: ISO and DIN;KMethod Specific;Alpha sort;D;DAlphabetic;DIA - DICMethod Specific;Endocrine Disruptors (Draft);EPA;Pesticides;Pesticides&Metabolites;INSECTICIDE;Agro-Products;Aromatics | | Mol File: | 115-32-2.mol |  |
| | Dicofol Chemical Properties |
| | Dicofol Usage And Synthesis |
| Chemical Properties | Pure dicofol is available as a white or grey powder or colourless crystal solid, while the technical dicofol is a red-brown or amber viscous liquid with an odour like fresh-cut hay. Dicofol undergoes decomposition on burning or on contact with acids, acid fumes, or bases producing toxic and corrosive fumes including hydrogen chloride.
Dicofol is combustible and incompatible with strong oxidising agents. Dicofol is soluble in most aliphatic and aromatic solvents and most common organic solvents but practically insoluble in water and hydrolyses in basic solution.
| | Chemical Properties | Pure dicofol is available as a white or gray powder or colorless solid crystals while the
technical dicofol is a red-brown or amber viscous liquid with an odor like fresh-cut hay.
Dicofol undergoes decomposition on burning or on contact with acids, acid fumes or bases,
producing toxic and corrosive fumes including hydrogen chloride. Dicofol is a persistent
OCP used as an acaricide and miticide. It is structurally similar to DDT. Dicofol is combustible
and incompatible with strong oxidizing agents. It is soluble in most aliphatic and
aromatic solvents and most common organic solvents, but practically insoluble in water
and hydrolyzes in basic solution. It is used on a wide variety of fruit, vegetables, ornamental
and fi eld crops. Dicofol is manufactured from DDT. Dicofol is corrosive to some
metals. It is used for foliar applications, mostly on cotton, apples, and citrus crops. Other
crops include strawberries, mint, beans, peppers, tomatoes, pecans, walnuts, stonefruit,
cucurbits, and non-residential lawns/ornamentals. | | Chemical Properties | Dicofol is a white or brown waxy solid | | Uses | Nonsystemic acaricide to control mites in citrus fruits, grapes, cotton, pome and stone fruit. | | Uses | Acaricide, organochlorine pesticide. Dicofol is a non-systemic acaricide/miticide currently registered in the US and Canada for use on a wide variety of crops. | | Definition | ChEBI: A tertiary alcohol that is DDT in which the benzylic hydrogen has been replaced by a hydroxy group. | | General Description | Dicofol or kelthane is a white crystalline, wettable powder dissolved in a liquid carrier, (water). The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Since Dicofol is a liquid Dicofol can easily penetrate the soil and contaminate groundwater and nearby streams. Dicofol can cause illness by inhalation, skin absorption, and/or ingestion. Dicofol is used as a pesticide. | | Air & Water Reactions | Hydrolyzed in alkaline media to dichlorobenzophenone and chloroform. Insoluble in water. | | Reactivity Profile | Dicofol is an organochlorine bridged diphenyl. Halogenated aliphatic compounds are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Halogenated aliphatics are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Dicofol hydrolyzes in alkali. Dicofol is slightly corrosive to metals. Contact with steel at elevated temperatures causes formation of toxic gases. . | | Health Hazard | Inhalation or ingestion causes nausea, headache, weight loss, convulsions, possible kidney and liver damage. Contact with eyes causes irritation. | | Health Hazard | Exposures to dicofol cause adverse health effects and poisoning. Occupational workers
suffer harmful effects on inhalation, ingestion and through skin contact. The symptoms
of poisoning include, but are not limited to, nausea, dizziness, weakness, and vomiting
from ingestion or respiratory exposure, skin irritation or rash from dermal exposure.
Dicofol-poisoned occupational workers show skin sensitization, conjunctivitis of the eyes,
and pathomorphological changes in the liver, kidneys, and CNS. After exposures to high
concentrations of dicofol, workers show nervousness, hyperactivity, headache, nausea,
vomiting, unusual sensations, fatigue, convulsions, coma, respiratory failure, and death.
However, published literature is limited and more data is required on occupational workers
as well as the general population. | | Agricultural Uses | Insecticide, Acaricide: Not approved for use in EU countries. Severely
Restricted for use in EU (containing>78% p,p'-dicofol or
1 g/kg of DDT and DDT-related compounds). Dicofol is
an organochlorine miticide/pesticide used for foliar applications,
mostly on cotton, apples, and citrus crops. Other
crops include: strawberries, mint, beans, peppers, tomatoes,
pecans, walnuts, stonefruit, cucurbits, and nonresidential
lawns/ornamentals. Formulations registered
for use on food/feed crops include emulsifiable concentrates,
and wettable powder formulations. These formulations
may be applied as concentrated or dilute sprays
using aircraft, duster, groundboom, and sprayer. Dicofol
is manufactured from DDT. In 1986, use of dicofol was
temporarily canceled by the U.S. EPA because of concerns
raised by high levels of DDT contamination. However,
it was reinstated when it was shown that modern manufacturing
processes can produce technical-grade dicofol
which contains <0.1% DDT. | | Trade name | ACARIN®[C]; CALLIFOL®; CARBAX®;
CEKUDIFOL®; DECOFOL®; DICOMITE®; DIFOL®;
FERRIAMICIDE®; FUMITE DICOFOL®; FW
293®; HIFOL®; KELTANE®; KELTHANE®; P,P'-
KELTHANE®; KELTHANETHANOL®; MILBOL®;
MITIGAN®; TIKTOK®; VAPCOTHION®, dicofol | | Potential Exposure | A potential danger to those
involved in manufacture, formulation and application of
this organochlorine pesticide. Used as acaricide (miticide)
in agricultural and nonagricultural applications. Similar
in structure to DDT. | | Environmental Fate | Plant. The major metabolite reported on apples is 4,4′-dichlorobenzophenone. On apples, dicofol concentrations decreased from 702 ppm to 436 ppm after 15 days. 4,4′Dichlorobenzophenone increased from 25.5 ppm at time of spraying to 25.5 ppm 15 days after spraying (Archer, 1974). Four days after spraying cucumbers with dicofol, residues decreased from 0.95–1.6 ppm to 0.4–1.5 ppm. No residues were detected 8 days after spraying (Nazer and Masoud, 1986). A half-life of 6 days was reported for dicofol in alfalfa (Akesson and Yates, 1964).
Chemical/Physical. When dicofol was exposed to sunlight for 20 days, a 10% yield of 4,4′-dichlorobenzophenone was obtained. Solvents containing dicofol and exposed to UV light resulted in the formation of chlorobenzilic acid esters (Vaidyanathasw | | Metabolic pathway | Dicofol(1) is an analogue of DDT. However, the replacement of a hydrogen
atom at position 1 by a hydroxyl group results in a fundamental
change in chemical properties and increases the lability of the molecule. It
breaks readily down to 4,4’-dichlorobenzophenone (2) thermally or on
hydrolysis and this compound is a major metabolite in mammals and
plants. | | Shipping | UN2996 Organochlorine pesticides, liquid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN3082 Environmentally hazardous substances, liquid, n.o.
s., Hazard class: 9; Labels: 9-Miscellaneous hazardous
material, Technical Name Required. | | Degradation | Dicofol is stable to acids but unstable in alkaline media in which it is
hydrolysed to 4,4’-dichlorobenzophenone(2) and chloroform (DT50 values
at pH 5, 7 and 9 are 85 days, 64-99 hours and 26 minutes, respectively).
The isomer, 2,2,2-trichloro-1-(2-chlorophenyl)-1-(4-chlorophenyl)ethanol
(o,p’-dicofol), is hydrolysed more rapidly.
Dicofol is degraded by light to 4,4’-dichlorobenzophenone (2) (PM). | | Incompatibilities | Incompatible with alkaline pesticides,
strong acids; acid fumes; aliphatic amines; isocyanates.
Halogenated aliphatic compounds are moderately or very
reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Halogenated aliphatics are incompatible with
strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds,
alkali metals, and epoxides. Dicofol hydrolyzes in alkali.
It is slightly corrosive to metals. Contact with steel at
elevated temperatures causes formation of toxic gases | | Waste Disposal | In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting
your local or federal environmental control agency, or by
contacting your regional EPA office. |
| | Dicofol Preparation Products And Raw materials |
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