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DICHLONE-CHLORANIL

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Classification   |    Detailed evidence-based information

Substances Included Synonyms

Therapeutic Toxic Class

    A) Dichlone is a yellow, odorless, crystal material that is used as a fungicide for vegetable seed treatment against seed decay. It is also used for certain apple, cherry, tomato, and rose diseases.

Specific Substances

    A) Dichlone
    1) Dichloronaphthoquinone
    2) 2,3-Dichloro-1,4-napthoquinone
    3) CAS 117-80-6
    4) 2,3-dichloro-1,4-naphthalenedione
    Chloranil
    1) Tetrachlorobenzoquinone
    2) Tetrachloroquinone
    3) 2,3,5,6-tetrachloro-1,4-benzoquinone
    4) CAS 118-75-2

    1.2.1) MOLECULAR FORMULA
    1) C10-H4-Cl2-O2

Available Forms Sources

    A) FORMS
    1) Dichlone is golden-yellow needles or leaflets from alcohol (Budavari, 1996).
    2) DICHLONE: Trade names include Phygon(R), Phygon XL(R), Algistat(R), Quintar(R), and Sanquinon(R).
    3) CHLORANIL: Trade name is Spergon(R).
    B) USES
    1) It is used as a fungicide for agriculture and textiles; as a herbicide and algicide; as an organic catalyst and seed disinfectant (Budavari, 1996; Lewis, 1997; Lewis, 1996).

Overview

Life Support

    A) This overview assumes that basic life support measures have been instituted.

Clinical Effects

    0.2.1) SUMMARY OF EXPOSURE
    A) Dichlone has a relatively low toxicity in both animals and humans and is poorly absorbed from the gastrointestinal tract.
    B) It is a skin, eye, and mucous membrane irritant. Large doses may cause central nervous system depression.
    C) Dichlone is a poison by ingestion and intraperitoneal routes; it is toxic by inhalation and mildly toxic by skin contact.
    0.2.4) HEENT
    A) Ocular irritation may be noted following eye exposure.
    0.2.7) NEUROLOGIC
    A) CNS depression and coma may develop following large doses.
    0.2.8) GASTROINTESTINAL
    A) Vomiting and diarrhea may be noted. Irritation of the oral mucous membranes may be noted.
    0.2.14) DERMATOLOGIC
    A) Dermal irritation may be noted following skin exposure.

Laboratory Monitoring

    A) Dichlone/Chloranil levels are not readily available or clinically useful.
    B) No specific lab work (CBC, electrolytes, urinalysis) is needed unless otherwise clinically indicated.

Treatment Overview

    0.4.2) ORAL/PARENTERAL EXPOSURE
    A) ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old.
    B) EMESIS: Ipecac-induced emesis is not recommended because of the potential for CNS depression.
    C) AVOID USING ANY OIL OR FAT since these agents may increase the irritant effects.
    D) METHEMOGLOBIN FORMATION, although rare, is a theoretical possibility and should be ruled out in patients with cyanosis or respiratory distress.
    1) METHEMOGLOBINEMIA: Determine the methemoglobin concentration and evaluate the patient for clinical effects of methemoglobinemia (ie, dyspnea, headache, fatigue, CNS depression, tachycardia, metabolic acidosis). Treat patients with symptomatic methemoglobinemia with methylene blue (this usually occurs at methemoglobin concentrations above 20% to 30%, but may occur at lower methemoglobin concentrations in patients with anemia, or underlying pulmonary or cardiovascular disorders). Administer oxygen while preparing for methylene blue therapy.
    2) METHYLENE BLUE: INITIAL DOSE/ADULT OR CHILD: 1 mg/kg IV over 5 to 30 minutes; a repeat dose of up to 1 mg/kg may be given 1 hour after the first dose if methemoglobin levels remain greater than 30% or if signs and symptoms persist. NOTE: Methylene blue is available as follows: 50 mg/10 mL (5 mg/mL or 0.5% solution) single-dose ampules and 10 mg/1 mL (1% solution) vials. Additional doses may sometimes be required. Improvement is usually noted shortly after administration if diagnosis is correct. Consider other diagnoses or treatment options if no improvement has been observed after several doses. If intravenous access cannot be established, methylene blue may also be given by intraosseous infusion. Methylene blue should not be given by subcutaneous or intrathecal injection. NEONATES: DOSE: 0.3 to 1 mg/kg.
    3) Concomitant use of methylene blue with serotonergic drugs, including serotonin reuptake inhibitors (SRIs), selective serotonin reuptake inhibitors (SSRIs), serotonin and norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), norepinephrine-dopamine reuptake inhibitors (NDRIs), triptans, and ergot alkaloids may increase the risk of potentially fatal serotonin syndrome.
    0.4.5) DERMAL EXPOSURE
    A) OVERVIEW
    1) DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).

Range Of Toxicity

    A) Dichlone has a relatively low index of toxicity in both animals and humans. It is considered moderately toxic by some sources.
    B) CHLORANIL - The acute oral LD50 for rats is 4 grams/kg.

Clinical Effects

Summary Of Exposure

    A) Dichlone has a relatively low toxicity in both animals and humans and is poorly absorbed from the gastrointestinal tract.
    B) It is a skin, eye, and mucous membrane irritant. Large doses may cause central nervous system depression.
    C) Dichlone is a poison by ingestion and intraperitoneal routes; it is toxic by inhalation and mildly toxic by skin contact.

Heent

    3.4.1) SUMMARY
    A) Ocular irritation may be noted following eye exposure.
    3.4.3) EYES
    A) Irritation of the eye and cornea may occur (Dreisbach, 1983; Lewis, 1997; Gosselin et al, 1984).

Neurologic

    3.7.1) SUMMARY
    A) CNS depression and coma may develop following large doses.
    3.7.2) CLINICAL EFFECTS
    A) CENTRAL NERVOUS SYSTEM DEFICIT
    1) Large doses may cause CNS depression and coma (Dreisbach, 1983; Sax & Lewis, 1989; Gosselin et al, 1984; Budavari, 1996; Sax & Lewis, 1987).

Gastrointestinal

    3.8.1) SUMMARY
    A) Vomiting and diarrhea may be noted. Irritation of the oral mucous membranes may be noted.
    3.8.2) CLINICAL EFFECTS
    A) VOMITING
    1) Ingestion of large doses usually results in prompt emesis. May irritate the mucous membranes (Dreisbach, 1983).
    B) DIARRHEA
    1) Chloranil has been noted to produce watery diarrhea (Gosselin et al, 1984).

Hepatic

    3.9.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) HEPATOCELLULAR DAMAGE
    a) RATS - Dichlone caused swelling of rat liver mitochondria, a process which was shown to be osmotic in nature (Pritsos et al, 1985). Consistent with these in vitro findings, dichlone feeding caused partial uncoupling of liver and heart mitochondria (Pritsos et al, 1985). These findings indicate that diclone affects cellular energy metabolism by inducing oxidative stress at the organelle level and by interacting with key mitochondrial thiol groups.

Dermatologic

    3.14.1) SUMMARY
    A) Dermal irritation may be noted following skin exposure.
    3.14.2) CLINICAL EFFECTS
    A) SKIN IRRITATION
    1) Dichlone or chloranil may produce dermal irritation. Irritation is enhanced by the application of oils and other fatty substances, including perspiration (Gosselin et al, 1984).

Carcinogenicity

    3.21.1) IARC CATEGORY
    A) IARC Carcinogenicity Ratings for CAS117-80-6 (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004):
    1) Not Listed
    3.21.3) HUMAN STUDIES
    A) CARCINOMA
    1) Dichlone is listed as an experimental carcinogen (Sax & Lewis, 1989).
    B) ANIMAL STUDIES
    1) Oral doses of 3300 mg/kg in mice were found to be neoplastic (RTECS , 1991).
    2) Subcutaneous doses of 22 mg/kg in mice were carcinogenic (RTECS , 1991).

Laboratory Monitoring

Monitoring Parameters Levels

    4.1.1) SUMMARY
    A) Dichlone/Chloranil levels are not readily available or clinically useful.
    B) No specific lab work (CBC, electrolytes, urinalysis) is needed unless otherwise clinically indicated.

Treatment

Life Support

    A) Support respiratory and cardiovascular function.

Monitoring

    A) Dichlone/Chloranil levels are not readily available or clinically useful.
    B) No specific lab work (CBC, electrolytes, urinalysis) is needed unless otherwise clinically indicated.

Oral Exposure

    6.5.1) PREVENTION OF ABSORPTION/PREHOSPITAL
    A) EMESIS
    1) EMESIS: Ipecac-induced emesis is not recommended because of the potential for CNS depression.
    B) ACTIVATED CHARCOAL
    1) PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION
    a) Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002).
    1) In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis.
    2) The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.2) PREVENTION OF ABSORPTION
    A) EMESIS/NOT RECOMMENDED
    1) EMESIS: Ipecac-induced emesis is not recommended because of the potential for CNS depression.
    B) ACTIVATED CHARCOAL
    1) CHARCOAL ADMINISTRATION
    a) Consider administration of activated charcoal after a potentially toxic ingestion (Chyka et al, 2005). Administer charcoal as an aqueous slurry; most effective when administered within one hour of ingestion.
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.3) TREATMENT
    A) IRRITATION SYMPTOM
    1) Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury.
    B) DIETARY FINDING
    1) Oils and fats should be avoided for at least 24 hours since they increase the irritant effects.
    C) METHEMOGLOBINEMIA
    1) Methemoglobin formation is a theoretical possibility.
    2) SUMMARY
    a) Determine the methemoglobin concentration and evaluate the patient for clinical effects of methemoglobinemia (ie, dyspnea, headache, fatigue, CNS depression, tachycardia, metabolic acidosis). Treat patients with symptomatic methemoglobinemia with methylene blue (this usually occurs at methemoglobin concentrations above 20% to 30%, but may occur at lower methemoglobin concentrations in patients with anemia, or underlying pulmonary or cardiovascular disorders). Administer oxygen while preparing for methylene blue therapy.
    3) METHYLENE BLUE
    a) INITIAL DOSE/ADULT OR CHILD: 1 mg/kg IV over 5 to 30 minutes; a repeat dose of up to 1 mg/kg may be given 1 hour after the first dose if methemoglobin levels remain greater than 30% or if signs and symptoms persist. NOTE: Methylene blue is available as follows: 50 mg/10 mL (5 mg/mL or 0.5% solution) single-dose ampules (Prod Info PROVAYBLUE(TM) intravenous injection, 2016) and 10 mg/1 mL (1% solution) vials (Prod Info methylene blue 1% intravenous injection, 2011). REPEAT DOSES: Additional doses may be required, especially for substances with prolonged absorption, slow elimination, or those that form metabolites that produce methemoglobin. NOTE: Large doses of methylene blue may cause methemoglobinemia or hemolysis (Howland, 2006). Improvement is usually noted shortly after administration if diagnosis is correct. Consider other diagnoses or treatment options if no improvement has been observed after several doses. If intravenous access cannot be established, methylene blue may also be given by intraosseous infusion. Methylene blue should not be given by subcutaneous or intrathecal injection (Prod Info methylene blue 1% intravenous injection, 2011; Herman et al, 1999). NEONATES: DOSE: 0.3 to 1 mg/kg (Hjelt et al, 1995).
    b) CONTRAINDICATIONS: G-6-PD deficiency (methylene blue may cause hemolysis), known hypersensitivity to methylene blue, methemoglobin reductase deficiency (Shepherd & Keyes, 2004)
    c) FAILURE: Failure of methylene blue therapy suggests: inadequate dose of methylene blue, inadequate decontamination, NADPH dependent methemoglobin reductase deficiency, hemoglobin M disease, sulfhemoglobinemia, or G-6-PD deficiency. Methylene blue is reduced by methemoglobin reductase and nicotinamide adenosine dinucleotide phosphate (NADPH) to leukomethylene blue. This in turn reduces methemoglobin. Red blood cells of patients with G-6-PD deficiency do not produce enough NADPH to convert methylene blue to leukomethylene blue (do Nascimento et al, 2008).
    d) DRUG INTERACTION: Concomitant use of methylene blue with serotonergic drugs, including serotonin reuptake inhibitors (SRIs), selective serotonin reuptake inhibitors (SSRIs), serotonin and norepinephrine reuptake inhibitors (SNRIs), tricyclic antidepressants (TCAs), norepinephrine-dopamine reuptake inhibitors (NDRIs), triptans, and ergot alkaloids may increase the risk of potentially fatal serotonin syndrome (U.S. Food and Drug Administration, 2011; Stanford et al, 2010; Prod Info methylene blue 1% IV injection, 2011).
    4) TOLUIDINE BLUE OR TOLONIUM CHLORIDE (GERMANY)
    a) DOSE: 2 to 4 mg/kg intravenously over 5 minutes. Dose may be repeated in 30 minutes (Nemec, 2011; Lindenmann et al, 2006; Kiese et al, 1972).
    b) SIDE EFFECTS: Hypotension with rapid intravenous administration. Vomiting, diarrhea, excessive sweating, hypotension, dysrhythmias, hemolysis, agranulocytosis and acute renal insufficiency after overdose (Dunipace et al, 1992; Hix & Wilson, 1987; Winek et al, 1969; Teunis et al, 1970; Marquez & Todd, 1959).
    c) CONTRAINDICATIONS: G-6-PD deficiency; may cause hemolysis.

Inhalation Exposure

    6.7.1) DECONTAMINATION
    A) Move patient from the toxic environment to fresh air. Monitor for respiratory distress. If cough or difficulty in breathing develops, evaluate for hypoxia, respiratory tract irritation, bronchitis, or pneumonitis.
    B) OBSERVATION: Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.
    C) INITIAL TREATMENT: Administer 100% humidified supplemental oxygen, perform endotracheal intubation and provide assisted ventilation as required. Administer inhaled beta-2 adrenergic agonists, if bronchospasm develops. Consider systemic corticosteroids in patients with significant bronchospasm (National Heart,Lung,and Blood Institute, 2007). Exposed skin and eyes should be flushed with copious amounts of water.

Eye Exposure

    6.8.1) DECONTAMINATION
    A) EYE IRRIGATION, ROUTINE: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, an ophthalmologic examination should be performed (Peate, 2007; Naradzay & Barish, 2006).

Dermal Exposure

    6.9.1) DECONTAMINATION
    A) DERMAL DECONTAMINATION
    1) DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. Rescue personnel and bystanders should avoid direct contact with contaminated skin, clothing, or other objects (Burgess et al, 1999). Since contaminated leather items cannot be decontaminated, they should be discarded (Simpson & Schuman, 2002).
    6.9.2) TREATMENT
    A) IRRITATION SYMPTOM
    1) Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines.
    B) Treatment should include recommendations listed in the ORAL EXPOSURE section when appropriate.

Range Of Toxicity

Summary

    A) Dichlone has a relatively low index of toxicity in both animals and humans. It is considered moderately toxic by some sources.
    B) CHLORANIL - The acute oral LD50 for rats is 4 grams/kg.

Minimum Lethal Exposure

    A) GENERAL/SUMMARY
    1) This material is moderately toxic to humans by ingestion; between 1 ounce and 1 pound may be fatal (OHM/TADS , 1992).

Maximum Tolerated Exposure

    A) GENERAL/SUMMARY
    1) Dichlone has a relatively low toxicity in both animals and humans. It has a toxicity rating of 3 (moderately toxic) according to Gosselin (1984).

Workplace Standards

    A) ACGIH TLV Values for CAS117-80-6 (American Conference of Governmental Industrial Hygienists, 2010):
    1) Not Listed

    B) NIOSH REL and IDLH Values for CAS117-80-6 (National Institute for Occupational Safety and Health, 2007):
    1) Not Listed

    C) Carcinogenicity Ratings for CAS117-80-6 :
    1) ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed
    2) EPA (U.S. Environmental Protection Agency, 2011): Not Listed
    3) IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed
    4) NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed
    5) MAK (DFG, 2002): Not Listed
    6) NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed

    D) OSHA PEL Values for CAS117-80-6 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
    1) Not Listed

Toxicity Information

    7.7.1) TOXICITY VALUES
    A) References: RTECS, 1992 Sax & Lewis, 1989
    1) LD50- (INTRAPERITONEAL)MOUSE:
    a) 30 mg/kg
    2) LD50- (ORAL)MOUSE:
    a) 440 mg/kg
    3) LD50- (ORAL)RAT:
    a) 160 mg/kg

Pharmacology Toxicology

Toxicologic Mechanism

    A) When dichlone is heated to decomposition, it emits toxic chloride fumes (Lewis, 1996).
    B) A study by Elliott & Pardini (1988) suggests that dichlone exposure leads to an increase in hepatic cytochrome P-450 levels and activities which trigger the formation of a semiquinone intermediate which leads to oxidative stress. Thus, dichlone induces generation of toxic oxygen radicals.

Physicochemical

Physical Characteristics

    A) Dichlone is golden yellow needles or leaflets from alcohol (Budavari, 1996).

Molecular Weight

    A) Dichlone: 227.06
    B) Chloranil: 245.89

Animal Toxicology

Clinical Effects

    11.1.3) CANINE/DOG
    A) Dogs vomited and survived large single doses. They tolerated 500 ppm in food for one year, showing only slight liver damage (Gosselin et al, 1984).
    11.1.7) ICHTHYOID/FISH
    A) Dichlone and related compounds are used as aquatic herbicides. If applied at greater than 0.5 ppm, these compounds will cause fish kill (Thomson, 1985).

Range Of Toxicity

    11.3.2) MINIMAL TOXIC DOSE
    A) RODENT
    1) The maximum tolerated dose of chloranil in mice by the intraperitoneal route was 3.92 mg/kg (Anon, 1949).

References

General Bibliography

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