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HCID 18771Erstellt: 27. Oktober 2026

Dithianon (ISO)

Dithiocarbamates · CLUSTER · DELAN · it931 · AKTUAN · mv119a · thynon · DELAN(R)

https://huagongshe.com/de/chemical/18771

Molekülstruktur von Dithianon (ISO)

Identifikatoren & physikalische Daten

CAS No.3347-22-6
SummenformelC14H4N2O2S2
Durchschnittliche Molmasse296,3 g/mol
Monoisotopische Masse295,97141937 g/mol
SMILESN#Cc1sc2c(=O)c3ccccc3c(=O)c=2sc1C#N
InChIKeyPYZSVQVRHDXQSL-UHFFFAOYSA-N
PubChem CID18771
ChEMBLCHEMBL2228641
ChEBICHEBI:81842
EC No.222-098-6
DTXSIDDTXSID8040270
Lokaler NameDithianon (ISO)

Chemische & physikalische Eigenschaften

XLogP2,8
Polarare Oberfläche (TPSA)132
H-Brücken-Donoren0
H-Brücken-Akzeptoren6
Frei drehbare Bindungen0
Schwere Atome20
Formalladung0
Komplexität628
PestizideAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> FungicidesEnvironmental transformation -> Pesticides (parent, predecessor)
LogP (Verteilungskoeffizient)log Kow = 2.84
GeruchOdorless
Dichte1.58 g/cu cm at 20 °Cd18 1.55
Color/FormDark brown crystals, with a coppery luster
LöslichkeitSol in dioxane, chlorobenzeneSoluble in acetoneSolubility = 12 g/L in chloroform, 10 g/L in acetone, and 8 g/L in benzene at 20 °CSparingly soluble in methanol and dichloromethaneIn water, 0.14 mg/L at 20 °C0.14 mg/L @ 20 °C (exp)0.5mg/L(temperature not stated)
CorrosivityNoncorrosive
FlammpunktIgnition temperature >300 °C
Schmelzpunkt220 °C225 °C225°
Dampfdruck2.03X10-11 mm Hg at 25 °C
Physical DescriptionBrown odorless solid[Merck Index]
Stability/Shelf LifeStable up to 80 °C.Decomposed by alkaline media, by concentrated acids, and by prolonged heating... .
Siedepunkt402.1±45.0 °C(Predicted)
Brechungsindex1.6360 (estimate)
Lagerbedingungen0-6°C
Merck13,3404
BRN1325563
Henry-Konstante1.7×105 mol/(m3Pa) at 25℃, HSDB (2015)
Hauptanwendungenagricultureenvironmental
InChI1S/C14H4N2O2S2/c15-5-9-10(6-16)20-14-12(18)8-4-2-1-3-7(8)11(17)13(14)19-9/h1-4H
InChIKeyPYZSVQVRHDXQSL-UHFFFAOYSA-N
SMILESO=C1C2=C(SC(C#N)=C(S2)C#N)C(=O)c3ccccc13
LogP (Verteilungskoeffizient)2.840
CAS Datenbank3347-22-6(CAS DataBase Reference)
NIST chemische InformationenDithianone(3347-22-6)
EPA chemische InformationenDithianon (3347-22-6)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P317, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P320, P321, P330, P333+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Regulatorische InformationenCommission Implementing Regulation (EU) No 540/2011 (amended)Dithianon is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2011/41/EU, Reg. (EU) 2018/1266, Reg. (EU) 2020/2007, Reg. (EU) 2024/1206, Reg. (EU) No 540/2011Dithianon: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Weitere SicherheitsinformationenIMAP assessments - Naphtho[2,3-b]-1,4-dithiin-2,3-dicarbonitrile, 5,10-dihydro-5,10-dioxo-: Human health tier I assessment
GefahrenübersichtAllergic contact dermatitis reported in farmworkers[Kanerva, p. 1792] Eye irritation and effects to skin, including erythema, swelling, and itching, reported in employees of manufacturing plant, with erythema, swelling, itching, blistering, and peeling of the skin reported in spray operatorsPatch testing has shown that skin sensitization may occurCauses liver and kidney injury in animal studies[EFSA] May cause irritationHarmful by ingestion and inhalation[Aldrich MSDS]
Toxic Combustion ProductsWhen heated to decomposition it emits very toxic fumes of /hydrogen cyanide and nitrogen and sulfur oxides/.
Hazard Classes and CategoriesAcute Tox. 4 (100%)Acute toxicity - category 4Acute toxicity (Oral) - Category 4Acute Tox. 4 *

Anwendungen & Verwendung

Beschreibung

Dithianone is an anthraquinone derivative, used as a fungicide. With cymoxanil, it is contained in Aktuan. Cases have been sparsely reported for agricultural workers.

History

The ethylenebisdithiocarbamates were rediscovered in 1945 when Dimond et al. (2) reported a “new water soluble protectant fungicide.” The parent compound, disodium ethylenebisdithiocarbamate, was highly soluble in water and was unstable in air, and it might have been only a laboratory curiosity and remained unnoticed but for the applications developed by Heuberger and Manns (3), who stabilized it by converting it into zinc salt by the addition of zinc sulfate–lime mixture. This was followed by the introduction of zineb as fungicide by the Rohm and Haas Company, USA. The same phenomenon was later confirmed by Barratt and Horsfall (4), who attributed the stabilizing effect as due to zinc salt formation. From the numerous compounds suggested by Hester (5), only disodium ethylenebisdithiocarbamate and its zinc and manganese salts are largely accepted for practical application. Research on these dithiocarbamates led to some promising variants.

Verwenden

Fungicide.

Skin, Eye, and Respiratory IrritationsUnder some conditions ... /dithianon/ may cause severe skin irritation in sensitive individuals.
Hazardous Reactivities and IncompatibilitiesIncompatible with petroleum oils, alkaline materials, and sulfur-containing compounds.
LagerbedingungenSafe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.
ReinigungsverfahrenIf a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.
EntsorgungsverfahrenSRP: 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.Dithianon is decomposed under alkaline conditions. Recommendable method: Incineration. Peer-review: Incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.
Preventive MeasuresAvoid exposure to skin, eyes, and of the respiratory tract mucous membranes.Wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracksdon't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.
ÖkotoxizitätswerteLC50 /Carassius auratus/ (Goldfish, weight 1.0 g) 150 ug/L/96 hr at 18 °C (95% confidence limit 66-330 ug/L) /Technical material/ /Conditions of bioassay not specified in source examined/LC50 Carassius auratus (Goldfish) 290 ug/L/24 hr (95% confidence interval: 231-364 ug/L)static /formulated product/LC50 /Pimephales promelas/ (Fathead minnow, weight 0.9 g) 165 ug/L/96 hr at 18 °C (95% confidence limit 123-223 ug/L) /Technical material/ /Conditions of bioassay not specified in source examined/LC50 Pimephales promelas (Fathead minnow) 168 ug/L/24 hr (95% confidence interval: 124-227 ug/L)For more Ecotoxicity Values (Complete) data for DITHIANON (14 total), please visit the HSDB record page.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 840(SRC), determined from a log Kow of 2.84(2) and a regression-derived equation(3), indicates that dithianon is expected to have low mobility in soil(SRC). Volatilization of dithianon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.7X10-11 atm-cu m/mole(SRC), determined from a vapor pressure of 2.03X10-11 mm Hg(4) and a water solubility of 0.14 mg/L(4). Dithianon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Dithianon (3.85 mg) was applied to a 15X15X15 cm alkaline sandy loam core (pH 8-9)the compound was shown to be unstable under alkaline conditions as indicated by 63-100% loss after 10 days(5). Biodegradation data were not available(SRC, 2006).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 840(SRC), determined from a log Kow of 2.84(2) and a regression-derived equation(3), indicates that dithianon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 5.7X10-11 atm-cu m/mole(SRC), derived from a vapor pressure of 2.03X10-11(4) and water solubility of 0.14 mg/L(4). According to a classification scheme(5), an estimated BCF of 85(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). A hydrolysis half-life range of <1 to 12 days and an aqueous photolysis half-life of 19.2 hours have been reported for dithianon(7). However, conditions such as temperature and pH were not provided. The half-life of dithianon in an aqueous solution (0.1 mg/L) exposed to artificial sunlight was 19 hours(4). Biodegradation data were not available(SRC, 2006).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), dithianon, which has a vapor pressure of 2.03X10-11 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase dithianon may be removed from the air by wet or dry deposition(SRC). Dithianon may undergo direct photolysis in the environment based on an aqueous photolysis half-life of 19 hours(3).
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ökotoxizitätsauszüge/AQUATIC SPECIES/ Dithianon had comparatively high toxicity to Bufo bufo japonicus and Rana catesbeiana tadpoles among 36 fungicides and 23 herbicides tested./AQUATIC SPECIES/ 2,3-Dicyano-1,4-dithiaanthraquinone added to water killed 2 of 4 catfish & rainbow trout exposed to 0.04 ppm for 72 hr while none of 4 goldfish were killed after 96 hr.
Acute Toxicity LinkChemical: DITHIANON
Soil Adsorption/MobilityThe Koc of dithianon is estimated as 840(SRC), using a log Kow of 2.84(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that dithianon is expected to have low mobility in soil. Dithianon (3.85 mg) applied to a 15X15X15 cm alkaline sandy loam core (pH 8-91-2% organic content) was immobilized in the top 2 cm of the soil(4). No leaching occurred after several weeks of irrigation(4).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Under some conditions ... /dithianon/ may cause severe skin irritation in sensitive individuals./CASE REPORTS/ Sensitivity to benomyl ... was observed in three patients, and to Captan ... Delan (Dithionone) ... and Pentac ... in two of the patients.
Artificial Pollution SourcesRegistration for dithianon's use as a pesticide in the US was cancelled in October, 1989(1). Dithianon's former US production and use as a fungicide(2) may have resulted in its direct release to the environment(SRC).
Environmental BioconcentrationAn estimated BCF of 85 was calculated for dithianon(SRC), using a log Kow of 2.84(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).
Volatilization from Water/SoilThe Henry's Law constant for dithianon is estimated as 5.7X10-11 atm-cu m/mole(SRC) derived from its vapor pressure, 2.03X10-11 mm Hg(1), and water solubility, 0.14 mg/L(1). This Henry's Law constant indicates that dithianon is expected to be essentially nonvolatile from moist soil or water surfaces(2). The potential for volatilization of dithianon from dry soil surfaces is not expected(SRC) based upon its vapor pressure(1).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ ... CYP-catalysed reactions have been studied in liver, kidney and lung microsomes from male and female Swiss albino CD1 mice treated i.p. with single (3 or 6 mg/kg body wt.) or repeated (3 mg/kg body wt. daily for 3 days) doses of dithianon. In liver, all testosterone hydroxylase (TH) activities were increased in the single treatment from 2.8- (6beta-, 16alpha- and 16beta-TH activities) to 16-fold (2beta-TH activity) in males at the lower dose. In contrast, activities were reduced from 33.3% (16beta- and 17-TH activities, lower dose) to 66.4% (16beta-TH activity, higher dose) in females. In kidney, a similar pattern of modulation was achieved: induction from 2.9- to 5-fold (6beta- and 2alpha-TH activities, higher and lower doses, respectively) in malessuppression from 47.4 to 50.2% (2alpha- and 2beta-TH activities, either at lower or higher doses) in females. In lung, a significant induction ranging from 7.1- to 29.3-fold (16alpha- and 2alpha-TH activities, respectively, lower dose) in males, and up to a 7-fold increase (2beta-TH activity, higher dose) in females was obtained. After repeated treatment, hepatic 6beta-, 16beta-, 2alpha- and 2beta-TH activities were reduced up to approximately 60% in males, whereas no effect was seen in females. In extrahepatic tissues, a generalized increase of different THs was observed./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In 2-yr feeding trials no toxic effect was observed in rats at 20 mg/kg and dogs at 40 mg/kg per day in diet./LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Groups of Crl:CD(SD)BR rats (50/sex/group) were fed diets containing 0, 20, 120 or 600 ppm dithianion (purity 92%) for 104 weeks. ...The incidence of fur staining and rough haircoat was increased in high-dose females. At high-dose, body-weight gain and food consumption were decreased in males up to week 24 and in females during the whole study. At 600 ppm and occasionally at 120 ppm, Hb-hemoglobin, RBC-red blood cell count, PCV-packed cell volume, and MCV-mean corpuscular volume were decreased in both sexes. T3-triiodothyronine levels were decreased at the highest dose. At 120 and 600 ppm, glucose, BUN-blood urea nitrogen and oe-GT-gamma-glutamyltransferase were increased in both sexes. Throughout the study cholesterol levels were decreased at the highest dose. No clear effects were observed in urinalysis. Relative kidney and liver weights were increased in both sexes at 600 ppm. The incidence of treatment related kidney lesions (glomerulonephropathy and tubular nephrosis) was increased in both sexes at 600 ppm. In the kidneys of females at this dose level, an increased incidence of proliferative tubules, adenomas and carcinomas was observed. In females at 120 ppm, glomerulonephropathy and tubular nephrosis showed an increased incidence. The NOAEL in this study was 20 ppm, equivalent to 1 mg/kg bw/day, based on non-neoplastic kidney lesions observed at 120 ppm./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Groups of 10 male and 20 female rats received 0, 20, 200 or 500 ppm dithianon (purity not specified) in the diet for 100 days before the initial mating. ...At the highest dose, body-weight gain was depressed in all generations and in the 200 ppm of the F2b generation. Litter size at birth was not affected but throughout the study entire litters tended to be lost completely before weaning so litter size at weaning was generally lower in treated groups than in control groups (none dose-related). In the F1b matings (both litters) the incidence of litter loss was increased at 500 ppm. Over the three generations a tendency to a lower mean pup weight at birth as well as at weaning was observed at 500 ppm. Pup mortality was very variable in both treated and control groups but at the highest dose pup mortality seemed to be increased in the F1a, F2a and F2b litters. Liver and kidney weights of F3b pups were increased in males and females at 500 ppm. Kidney weight was also increased in 200 ppm males as was adrenal weight in 500 ppm males. The NOAEL was 20 ppm, equivalent to 1 mg/kg bw/day, on the basis of decreased body-weight gain and increased kidney weight.For more Non-Human Toxicity Excerpts (Complete) data for DITHIANON (9 total), please visit the HSDB record page.
Environmental Abiotic DegradationA hydrolysis half-life range of <1 to 12.3 days and an aqueous photolysis half-life of 19.2 hours have been reported for dithianon in water(1). However, conditions such as temperature and pH were not provided. The half-life of dithianon in an aqueous solution (0.1 mg/L) exposed to artificial sunlight was 19 hours(2). Dithianon (3.85 mg) was applied to a 15X15X15 cm alkaline sandy loam core (pH 8-9)the compound was shown to be unstable under alkaline conditions as indicated by 63-100% loss after 10 days(3).
Wassergefährdungsklasse (WGK)3
UN-TransportnummerUN 3077
Zollcode29349990
RTECS-Nr.QL0700000
R-Sätze (R)22-50/53
ToxizitätLD50 orally in rats, guinea pigs: 638, 110 mg/kg (Amadori, Heupt)
GefahrensymboleXnN,N,Xn
Sicherheitshinweise (S)24-60-61
Gefahrenklasse6.1(b)Acute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1
VerpackungsgruppeIII
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten3347-22-6(Hazardous Substances Data)