２，３－ジシアノ－１，４－ジチアアントラキノン

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Fungicides

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

log Kow = 2.84

2.84

Dark brown crystals, with a coppery luster

BROWN CRYSTALS

Sol in dioxane, chlorobenzene

Soluble in acetone

Solubility = 12 g/L in chloroform, 10 g/L in acetone, and 8 g/L in benzene at 20 °C; Sparingly soluble in methanol and dichloromethane

In water, 0.14 mg/L at 20 °C

0.14 mg/L @ 20 °C (exp)

220 °C

225 °C

Brown odorless solid; [Merck Index]

Solid

Stable up to 80 °C.

Decomposed by alkaline media, by concentrated acids, and by prolonged heating... .

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)

Danger

H302 (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)

Commission 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 540/2011

Dithianon: 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.

Allergic 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 operators; Patch testing has shown that skin sensitization may occur; Causes liver and kidney injury in animal studies; [EFSA] May cause irritation; Harmful by ingestion and inhalation; [Aldrich MSDS]

Acute Tox. 4 (100%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Acute Tox. 4 *

Safe 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.

If 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.

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.

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.

Avoid 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 cracks; don'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.

LC50 /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); static /formulated product/

For more Ecotoxicity Values (Complete) data for DITHIANON (14 total), please visit the HSDB record page.

TERRESTRIAL 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).

/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.

The 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 8-9; 1-2% organic content) was immobilized in the top 2 cm of the soil(4). No leaching occurred after several weeks of irrigation(4).

/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.

An 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).

The 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).

/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 males; suppression 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.

A 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).

Groups of 5 laying hens were given capsules containing 0, 0.36 or 3.6 mg 14C-dithianon/day (purity 99.3%), orally for 5 consecutive days. These doses were equivalent to 3 or 30 ppm in the feed, respectively. Excreta and eggs were collected twice daily. Radioactivity was excreted very rapidly and at a constant rate. Irrespective of the dose, 4 days after the last administration, total recovery of 14C was about 94% of the dose with about 90% recovered in the excreta and 3-5% in the GIT contents. Detectable tissue residues were found in kidney and liver (0.03% and 0.02%, respectively). The 14C recovered in eggs comprised less than 0.01% of the total radioactive dose. The radioactivity in egg yolk was higher than in egg white and was maximal at sacrifice (0.005 mg/kg and 0.075 mg/kg at the low- and the high-dose, respectively)

No active pesticide product registrations in the US; [NPRIS] Used as fungicide and seed dressing for fruits, vegetables, coffee, and other crops; [HSDB] Used in Japan, Australia, New Zealand, South Africa, the EU, and South America as broad spectrum fungicide for pome fruit and hops; [Reference #1] Used as a preventative contact fungicide for pome, stone, and citrus fruits, grapes, nut trees, vegetables, cereals, and other crops; [EFSA]

Farming (Pesticides) [Category: Industry]

For dithianon (USEPA/OPP Pesticide Code: 099201) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Fungicide against many foliar diseases of pome & stone fruit but not against powdery mildews

Fungicide ... used as a ... seed dressing.

Pathogens controlled include Venturia spp (apple, cherry, & pear), Microthyriella rubi (apple), Coccomyces hiemalis & Stigmina carpophila (cherry), Monilia spp, Taphrina deformans & Tranzschelia discolor (apricot & peach), Plasmopara viticola (grape), Pseudoperonospora humuli (hop), Elsinoe fawcetti, & Phomopsis citri (citrus), Mycosphaerella fragrariae, & Diplocarpon earliana (strawberry), Colletotrichum coffeeanum (coffee), Cronartium ribicola, Drepanopeziza ribis, & Plasmopara ribicola (currant).

van Schoor et al, US patent 2,976,296 (1961 to E. Merck).

Made by the reaction of disodium 2,3-dimercaptomaleonitrile and 1,4-naphthoquinone.

... Reaction of dichlone with 2,3-dimercapto-2-butenedinitrile.

Dithianon is produced by reaction of hydrogen cyanide with carbon disulfide in dimethylformamide to yield dimercaptomaleic acid dinitrile; this intermediate is then treated with 2,3-dichloronaphthoquinone

WETTABLE POWDER (750 G ACTIVE INGREDIENT/KG); DISPERSION IN WATER (250 G/L).

DELAN

DELAN WP

DELAN (FUNGICIDE)

For more Formulations/Preparations (Complete) data for DITHIANON (12 total), please visit the HSDB record page.

Environmental transformation -> Pesticides (parent, predecessor)

Fungicides

FUNGICIDES

Product not marketed in USA. Basic producer: Celamerck GMBH & Co KG (Federal Republic of Germany) ...

It was introduced by E Merck (now Celamerck GMBH Co KG) as code numbers IT-931, MV119A & trade mark delan. ... incompatible with petroleum oil sprays.

Non-phytotoxic at the recommended application rates. ... Incompatible with mineral oils, alkaline preparations, and sulfur-containing preparations.