2,3-Dichloro-1,4-naphthoquinone
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2,3-Dichloro-1,4-naphthoquinone
structure -
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CAS No:
117-80-6
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Formula:
C10H4Cl2O2
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Chemical Name:
2,3-Dichloro-1,4-naphthoquinone
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Synonyms:
1,4-Naphthalenedione,2,3-dichloro-;1,4-Naphthoquinone,2,3-dichloro-;2,3-Dichloro-1,4-naphthalenedione;USR 604;Compound 604;Dichlone;2,3-Dichloro-1,4-naphthoquinone;Phygon;Phygon Seed Protectant;Sanquinon;Diclone;Algistat;Phygon XL;2,3-Dichloro-1,4-dihydro-1,4-dioxonaphthalene;Algistat (quinone);NSC 537;2,3-Dichloro-p-naphthoquinone;2,3-Dichloro-1,4-dihydronaphthalene-1,4-dione
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CAS No:
Description
YELLOW FINE CRYSTALLINE POWDER2,3-Dichloro-1,4-naphthoquinone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.
Dichlone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.
Dichlone is a yellow crystalline solid dissolved in a water-emulsifiable liquid carrier. Can cause illness by inhalation, skin absorption and/or ingestion. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Can easily penetrate the soil and contaminate groundwater and nearby streams. Used as a fungicide.
2,3-Dichloro-1,4-naphthoquinone Basic Attributes
227.04
227.04
1073511
204-210-5
C28BKZ2J9A
537
2902|2761
DTXSID7020425
Golden yellow needles or leaflets from alcohol.
29147090
Characteristics
34.1
2.65 (est)
Yellow Fine Crystalline Powder
1.4057 (rough estimate)
195 °C
275 °C @ Press: 2 Torr
275°C/2mm
1.5410 (estimate)
H2O: 0.008 g/L;Moderately soluble in ethyl acetate, acetic acid, dimethylformamide; sparingly soluble in alcohols
Store below +30°C.
1.1X10-6 mm Hg at 25 deg C
7.8 (Air = 1)
Oral-rat LD50: 160 mg/kg; Oral-Mouse LD50: 440 mg/kg
Thermal decomposition of toxic chloride gas
Henry's Law constant = 1.02X10-9 atm-cu m/mole at 25 °C (est)
In dry state, stable to the light and heat; in solution, slowly decomposed by light. Stable in acidic media, but hydrolyzed by alkalis.|Vapor concentration: 0.02 mg/L at 100 °C|Sublimes at greater than 32 °C|Hydroxyl radical reaction rate constant = 1.34X10-12 cu cm/molecule-sec at 25 °C (est)
Insoluble in water.
Ketones
DICHLONE is a halogenated ketone. Ketones are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.
Safety Information
III
6.1
UN 2811 6.1/PG 3
3
22-36/38-50/53
26-60-61
QL7525000
Xn,N
The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials
In the dry state, stable to light and heat. In solution, slowly decomposed by light. Stable in acidic media, but hydrolyzed by alkalis.
P273-P305 + P351 + P338-P501
H302-H315-H319-H410
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. Also, a good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. /1,4-Naphthoquinone/
Incompatible with petroleum oils, dinitro compounds, organomercury compounds, calcium arsenate, lime sulfur, Bordeaux mixture, nicotine, and emulsifiable concentrate formulations.|Incompatibilities: ... it is incompatible with sprays containing lime, calcium arsenate, mercury, dinitro-compounds, oil, or emulsifiable concentrates.
USEPA/OPP; PESTICIDE REGISTRATION STANDARD--2,3-DICHLORO-1,4-NAPHTHOQUINONE (DICHLONE); REPORT; EPA-540/RS-81-001; ORDER NO PB81-207383: 125 (1981). REGISTRATION STD FOR DICHLONE AND REQUIREMENTS FOR REGISTERING OR RE-REGISTERING PESTICIDE CONTAINING THE ACTIVE INGREDIENT ARE GIVEN.
Special Hazards of Combustion Products: Highly toxic fumes are imminent. (USCG, 1999)
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P391, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P305+P351+P338, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P391, and P501|Aggregated GHS information provided by 332 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P264, P270, P280, P301+P310, P302+P352, P305+P351+P338, P321, P330, P332+P313, P337+P313, P362, P405, and P501
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 151 [Substances - Toxic (Non-combustible)]: Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Self-contained breathing apparatus, rubber gloves, hats, suits, and boots. (USCG, 1999)|Personnel protection: ... Wear appropriate chemical protective gloves, boots, and goggles.|Self-contained breathing apparatus ... hats, suits ... .
If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.)
Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder.|Environmental considerations: Water spill: Use natural barriers or oil spill control booms to limit spill travel. If dissolved, in region of 10 ppm or greater concentration, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses.
Glycerol or silicone base protective skin cremes are recommended. Lanolin, Vaseline, or oil-based creams should not be used.|If material not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary.|Avoid skin contact or breathing dust, spray mist.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Irritating to skin, /and/ mucous membranes|Occupational exposure of humans to dust of 2,3-dichloro-1,4-naphthoquinone in concentration of 0.7-6 mg/cu m caused eye irritation.
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
RURAL/REMOTE: Dichlone was detected at a concentration of 1.8 ng/cu m in air samples collected in Pekin, IL in 1980(1).
Toxicity
highly toxic
LD50 Mouse ip 30 mg/kg|LD50 Rat oral 1,300 mg/kg|LD50 Rat oral 160 mg/kg|LD50 Rabbit percutaneous 5000 mg/kg|LD50 Mouse oral 440 mg/kg
/OTHER TERRESTRIAL SPECIES/ Southern armyworm, Spodoptera eridania, larvae were provided ad libitum 0.002-0.25% w/w dichlone, 2,3-dichloro-1,4-naphthoquinone (CNQ). Larval mortality occurred in a time-and-dose dependent manner, with an LC17 of 0.01% and an LC50 of 0.26% CNQ at day-5. Extracts of larvae fed control, 0.01, and 0.25% CNQ diets for 5 days were assayed for antioxidant enzymes. While 0.01% CNQ had a mild effect, 0.25% CNQ profoundly increased levels of all antioxidant enzymes that were examined. The increases as compared to control were: 5.3-, 1.9-, 3.2-, 2.6-, 2.8-, and 3.5-fold higher for superoxide dismutase, catalase, glutathione transferase and its peroxidase activity, glutathione reductase and DT-diaphorase, respectively. At 0.01% CNQ, the thiobarbituric acid reactive substances (TBARS) were similar to the control group. However, despite the induction from 0.25% CNQ of all enzymes examined, the lipid peroxidation was not attenuated; the TBARS were 29.7% over the control value. High mortalities and CNQ-induced pathologies reflected in retarded growth, wasting syndrome, and diuresis clearly indicated that the insect sustained severe oxidant-induced injuries before appropriate defenses were fully mobilized. Thus, this quinone causes an oxidative stress in a model insect species analogous to that observed in mammalian species.
Individuals at increased risk: those with chronic respiratory or skin diseases.
Dichlone's former use as a seed disinfectant, fungicide for foliage and textiles, and insecticide(1) resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Soil adsorption studies utilizing soil thin layer chromatography, soil column leaching and soil drench tests have found dichlone to be relatively immobile in soil(1). Volatilization of dichlone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.02X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Dichlone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.1X10-6 mm Hg(3). In a silt loam soil dissipation study (soil pH 6.4, temperature of 26 °C), loss of dichlone in moist soil followed first order kinetics with an observed rate constant of 0.7/day which corresponds to a half-life of about 1 day(4); in air-dried soil (pH 6.2), dissipation was much slower with 45 percent of initial dichlone remaining after 3 months(4). Results of degradation studies under fieldhouse conditions, utilizing both sterile and non-sterile tests, suggest that disappearance of dichlone in moist soil, freshwater and sewage is primarily abiotic in nature with some biotic involvement(5); in non-sterile samples of moist soil, sewage and fresh water, one-half of added dichlone disappeared in about 4, 3 and 4 days of incubation, respectively(5). The experimentally determined half-life of dichlone in water (pH 7, 29 °C) is 5 days(4), which suggests dichlone is disappearing in moist soil primarily due to aqueous hydrolysis(SRC).|TERRESTRIAL FATE: In a field test, the results of which were somewhat erratic due to lack of analytical sensitivity, dichlone applied to an apple orchard soil declined in concentration during the growing season and was not detected in the soil the following year. During the growing season, some dichlone was detected 4-6 inches below the surface(1).|AQUATIC FATE: Soil adsorption studies have found dichlone to be strongly adsorbed and relatively immobile in soil(1); therefore, dichlone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.02X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of 2.65(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Results of degradation studies, utilizing both sterile and non-sterile tests, suggest that disappearance of dichlone in moist soil, freshwater and sewage is primarily abiotic in nature with some biotic involvement(7); in non-sterile samples of moist soil, sewage and fresh water, one-half of added dichlone disappeared in about 4, 3 and 4 days of incubation, respectively(7). The experimentally determined half-life of dichlone in water (pH 7, 29 °C) is 5 days(8). In solution, dichlone is reported to decompose slowly by light(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dichlone, which has a vapor pressure of 1.1X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase dichlone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 12 days(SRC), calculated from its rate constant of 1.34X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase dichlone is also degraded in the atmosphere by reaction with ozone(SRC); the half-life for this reaction in air is estimated to be about 320 days(SRC), calculated from its rate constant of 3.6X10-19 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Dichlone absorbs at wavelengths >290 nm(4) and therefore is expected to be susceptible to direct photolysis by sunlight(SRC). Particulate-phase dichlone may be removed from the air by wet or dry deposition(SRC).
The rate constant for the vapor-phase reaction of dichlone with photochemically-produced hydroxyl radicals has been estimated as 1.34X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of dichlone with ozone has been estimated as 3.6X10-19 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 320 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Dichlone absorbs at wavelengths >290(3) and therefore may be susceptible to direct photolysis by sunlight(SRC). In solution, dichlone is reported to be slowly decomposed by light(4); it is reported to be stable in the dry state(4). Dichlone is stable in acidic media, but hydrolyzed by alkalis(4). The experimentally determined half-life of dichlone in a pH 7 buffered solution (containing 1% acetone) at 29 °C in the dark is 5 days(5).
An estimated BCF of 3 was calculated for dichlone(SRC), using an estimated log Kow of 2.65(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
9.55e+03 L/kg|Dichlone has been shown to be immobile in silty clay loam using soil thin layer chromatography as well as in soil columns and in soil drench tests(1). In one field test in which 0.4 lb/acre of active compound was applied to the soil in an apple orchard, 0.7 ppm dichlone was detected at 4-6 inch depth during the growing season. However the analytic method lacked sensitivity and results were erratic. None of the chemical survived to the next growing season(2).
The Henry's Law constant for dichlone is estimated as 1.02X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that dichlone is expected to be essentially nonvolatile from water surfaces(2). Dichlone is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.1X10-6 mm Hg at 25 °C(3).
GROUND WATER: Dichlone was detected (concentration and detection limit not reported) in one of 8190 ground water samples collected in California between May 1979 and April 1984(1). Maximum dichlone concentrations of 2.7 ug/L have been detected in California ground waters(2).
In a pesticide residue screening program conducted in San Antonio, TX between 1989 and 1991 on 6970 produce samples collected from a food store, dichlone (at a detection limit of 0.5 ppm) was detected in the following: 1 celery sample (0.5% of all celery samples); celery was one of 81 commodities sampled in the program and dichlone was not reported as being detected in the other 80 commodities(1). Dichlone was reported as detected as part of the US Food and Drug Administration Pesticide Monitoring of Foods during fiscal years 1978-1982 (detection limit, concentrations, specific samples not reported)(2).
Occupational exposure and general population exposure should be low or non-existent since dichlone is no longer produced or used in the US (1998)(1).
Drug Information
Experimental Therapy: Among 12 title compounds, I (R= hydrogen, chlorine, hydroxyl, methyl, methoxy, and Rl= hydrogen, chlorine, amino, phenylamino etc) tested for antitumor activity against ascitic sarcoma 180 in mice, 6 were prepared from 2,3-dichloro-1,4-naphthoquinone. ... /Dichlone was active against ascitic sarcoma 180 in mice in vivo/. Statistical analysis showed that the most important parameter determining their effectiveness in prolonging the life of tumor-bearing mice is their redox potentials. Although the toxicities of the /agents/ are also related to the redox potentials in the same way, their therapeutic indicies can be improved by adding substituents of greater lipophilicity.
Absorption: Poor from gastrointestinal tract.|It is poorly absorbed ... .
Exposures to the three 1,4-naphthoquinone (NQs) reduced intracellular glutathione levels in both cell types. For the BF-2 and HepG2 cells, pretreatments with buthionine sulfoximine (BSO), a glutathione-depleting agent, potentiated the cytotoxicity of 5,8-hydroxy-1,4-NQ and dichlone; pretreatment with dicoumarol, an inhibitor of DT-diaphorase, had no effect on toxicity of these two NQs. Apparently, for these two quinones the predominant metabolic pathway in both the BF-2 and HepG2 cells involved redox cycling via a one-electron reduction reaction, generating reactive oxygen intermediates that consumed intracellular glutathione. Pretreatment of the BF-2 cells with BSO, but not with dicoumarol, potentiated the toxicity of 1,4-NQ, again indicating that metabolism occurred via one electron reduction. However, for the HepG2 cells, pretreatment with dicoumarol, but not with BSO, potentiated the cytotoxicity of 1,4-NQ. Apparently, in the HepG2, as compared to the BF-2, cells, 1,4-NQ was metabolized by DT-diaphorase in a reaction involving a two electron reduction.|In plant cells, both chlorine atoms are replaced by sulphydryl groups to give a substituted dimercapto compound.
Dichlone can alter the permeability of the cell membrane, which may be one of the sites of action of this pesticide in fibroblastic cells. By a direct interaction with membrane components, dichlone enters the cell rapidly and stimulates oxygen uptake, probably by constituting a bypass of electron transfer.|Experiments indicated that the key oxidation of glucose, acetate, pyruvate, and alpha-ketoglutarate were inhibited by dichlone.|A central nervous system depressant. Reacts with enzyme thiols.|Dichlone is a potent alkylating agent, undergoing substitution reactions with amines.|For more Mechanism of Action (Complete) data for DICHLONE (6 total), please visit the HSDB record page.
INHALATION: Irritation to mucous membrane. EYES: Irritation. SKIN: Irritation. INGESTION: Can cause CNS depression. (USCG, 1999)
Call a physician. EYES: Flush with water. SKIN: Wash. INGESTION: Gastric lavage for large doses. For small doses, give activated charcoal, follow in 3 to 4 hours with sodium sulfate cathartic. (USCG, 1999)
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
/SIGNS AND SYMPTOMS/ Occupational exposure of humans to dust of 2,3-dichloro-1,4-naphthoquinone in concentration of 0.7-6 mg/cu m caused specific symptoms, including eye irritation, tightness in the chest, burning in the nasal passages, dermatitis, and decrease in number of erythrocytes and SH-groups in the blood.|/SIGNS AND SYMPTOMS/ ...CNS depressant.|/OTHER TOXICITY INFORMATION/ Dichlone (3X10-5 to 1X10-3 molar) induced rapid loss of intracellular potassium from normal human erythrocytes, and leakage of potassium (+) varied with the fungicide and cell concentration. Dichlone also increased osmotic fragility and inhibited sodium(+)-potassium (+)-ATPase, which is associated with active ion transport. Hemolysis occurred at concentrations higher than those which resulted in potassium (+) loss. Hemoglobin loss appeared to be due primarily to osmotic swelling of the treated cells.
2,3-dichloro-1,4-naphthoquinone
2,3-Dichloro-1,4-naphthoquinone Use and Manufacturing
Derived from 1, 4-naphthoquinone chloride. The chlorination operation is carried out in acetic anhydride or dinitrobenzene or alcohols, phenols, hydrocarbon solvents. The catalyst is bromine or iron powder and ferric chloride. It can also be obtained by chlorination of 1, 4-aminonaphthalenesulfonic acid in 50% dilute sulfuric acid solution with iron as a catalyst at 80°C.
Fungicide for agriculture and textiles; herbicide.
(1986) 10 thousand-500 thousand pounds|(1994) 10 thousand-500 thousand pounds
(1975): 9.1X10+7 g.|(1978): 9.1X10+7 g, ... est to have been exclusively for seed treatment of vegetables, mainly tomatoes, peas, and beans.|Apples, 67%; other deciduous fruit and seed treatment, 33% (1982 fungicide use)
50% WP; 1, 1.5, 2, 3, AND 4% DUSTS; 55% PASTE (FOR SEED TREATMENT).|Dichlone 50% wettable powder fungicide, Dichlone-sulfur 1.5-3.0 dust.|Kolo-100 is a mixture of 35 g of dichlone and 754 g of sulfur/kg.|Technical grade /is/ 95% pure.|For more Formulations/Preparations (Complete) data for DICHLONE (10 total), please visit the HSDB record page.
1,4-Naphthalenedione, 2,3-dichloro-: ACTIVE|Compatible with many common fungicides and wettable-powder insecticides.|It is generally used at dosage of 3/4-1 lb/100 gal. of spray. ... As dry seed treatment ... /rates vary/ from 1-4 oz/100 lb of seed.|Not produced commercially in USA.|Introduced by Uniroyal Inc and by FMC Corp. (US patents 2,302,384; 2,349,772 to Uniroyal).|Yields of up to 96% can be obtained by direct chlorination of 1,4-naphthoquinone if the chlorination is carried out in carbon tetrachloride at 50 °C.
Product analysis is by colorimetry after alkaline hydrolysis to the sodium salt of 2-chloro-3-hydroxy-1,4-naphthoquinone. ... Residues may be determined by GLC ... or by colorimetry ... .|Determination of the fungicide dichlone by normal and first-derivative spectrofluorimetry. The influence of solvents on the sensitivity of the spectrofluorometric detection of dichlone is discussed. Linear normal and first-derivative relative std deviations are 3.8 and 2.2%, resp. The derivative method is less affected by the presence of other insecticides, eg, kepone, thiodan, and monocrotophos.|Results are reported of a preliminary trial to establish the systematic identification and quantitative determination of various types of pesticides from their mixtures, by column chromatography, thin-layer chromatography and gas chromatography. Results are presented regarding the analysis of a mixture of the insecticides /including dichlone/.|An electrochemical detection approach for liquid chromatography is described utilizing two sequential, generator/detector electrodes. Analytes are first electrolyzed, and the reaction products are then detected electrochemically at a second electrode. In some cases, this allows the detection of analytes with high redox potentials, with good sensitivity and selectivity. The technique is tested on several organic analytes including dichlone.|For more Analytic Laboratory Methods (Complete) data for DICHLONE (8 total), please visit the HSDB record page.
Agrochemicals -> Fungicides|FUNGICIDES
Computed Properties
Molecular Weight:227.04
XLogP3:3.4
Hydrogen Bond Acceptor Count:2
Exact Mass:225.9588348
Monoisotopic Mass:225.9588348
Topological Polar Surface Area:34.1
Heavy Atom Count:14
Complexity:301
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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