115-32-2 Usage
Description
Dicofol, also known as Kelthane, is a white crystalline, wettable powder that is dissolved in a liquid carrier, typically water. It is a tertiary alcohol derived from DDT, where the benzylic hydrogen has been replaced by a hydroxy group. Dicofol is a non-systemic acaricide and miticide, structurally similar to DDT, and is used as a pesticide. It is a persistent organic compound and is combustible, incompatible with strong oxidizing agents, and soluble in most aliphatic and aromatic solvents. However, it is practically insoluble in water and hydrolyzes in basic solutions.
Uses
Used in Agricultural Industry:
Dicofol is used as an acaricide and miticide for controlling mites in a wide variety of crops. It is particularly used for foliar applications on cotton, apples, and citrus crops. Other crops that benefit from Dicofol treatment include strawberries, mint, beans, peppers, tomatoes, pecans, walnuts, stonefruit, cucurbits, and non-residential lawns/ornamentals. Dicofol is manufactured from DDT and is available in various formulations such as emulsifiable concentrates and wettable powder formulations, which can be applied as concentrated or dilute sprays using different application methods like aircraft, duster, groundboom, and sprayer.
Used in Pest Control:
Dicofol is used as a non-systemic acaricide/miticide to control mites in citrus fruits, grapes, cotton, pome, and stone fruit. It is currently registered for use in the US and Canada on a wide variety of crops. The primary hazard associated with Dicofol is its threat to the environment, as it can easily penetrate the soil and contaminate groundwater and nearby streams. Immediate steps should be taken to limit its spread to the environment. Dicofol can cause illness through inhalation, skin absorption, and/or ingestion.
It is important to note that Dicofol is not approved for use in EU countries and is severely restricted for use in the EU (containing >78% p,p'-dicofol or 1 g/kg of DDT and DDT-related compounds). In 1986, the use of Dicofol was temporarily canceled by the U.S. EPA due to 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 containing less than 0.1% DDT.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 115-32-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 5 respectively; the second part has 2 digits, 3 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 115-32:
(5*1)+(4*1)+(3*5)+(2*3)+(1*2)=32
32 % 10 = 2
So 115-32-2 is a valid CAS Registry Number.
InChI:InChI=1/C14H9Cl5O/c15-11-5-1-9(2-6-11)13(20,14(17,18)19)10-3-7-12(16)8-4-10/h1-8,20H
115-32-2Relevant articles and documents
Selective oxidation of DDT by dioxygen on the dioxo-Mo(VI) complex anchored on a TiO2 under UV-irradiation
Bakhtchadjian,Manucharova,Tavadyan
, p. 193 - 195 (2015)
Oxidation of DDT (1,1,1-trichloro-2,2-bis(4-chlorophenyl)ethane) by the dioxo-Mo(VI) complex (dioxo-molybdenum(VI)-dichloro[4,4′-dicarboxylato-2,2′-bipyridine]), anchored on a TiO2, in the presence of dioxygen under UV-irradiation (λ = 253.7 nm) in acetonitrile suspension has been examined. The reaction has catalytic character. Conversion of DDT (35% for 32 h reaction) to dicofol (2,2,2-trichloro-1,1-bis(4-chlorophenyl)ethanol, 21%) and a great number of other chlorinated and non-chlorinated products of the oxidative/reductive decomposition proceeds by the primary reaction of oxo-atom transfer from dioxo-Mo(VI) complex to bibenzylic-carbon atom of DDT. The catalytic cycle is performed via the re-oxidation of the reduced Mo(IV) into Mo(VI) by dioxygen in the "dark" reaction.
Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives
-
, (2008/06/13)
The invention relates to novel cis-alkoxyspiro-substituted tetramic acid derivatives of the formula (I), in which A, G, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly cis-alkoxyspiro-substituted tetramic acid derivatives and secondly a crop plant compatibility-improving compound.
Glyoxyl acid amides, method for producing them and their use for controlling harmful organisms
-
, (2008/06/13)
The invention relates to novel gloyoxylic acid amides, to a process for their preparation and to their use for controlling harmful organisms.
