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Dithianon

Dithianon structure

Dithianon 

structure
  • CAS No:

    3347-22-6

  • Formula:

    C14H4N2O2S2

  • Chemical Name:

    Dithianon

  • Synonyms:

    Naphtho[2,3-b]-1,4-dithiin-2,3-dicarbonitrile,5,10-dihydro-5,10-dioxo-;Naphtho[2,3-b]-p-dithiin-2,3-dicarbonitrile,5,10-dihydro-5,10-dioxo-;5,10-Dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithiin-2,3-dicarbonitrile;MV 119A;Dithianon;Stauffer MV 119A;Delan WP;Delan (fungicide);2,3-Dicyano-1,4-dithiaanthraquinone;2,3-Dinitrilo-1,4-dithiaanthraquinone;Dithianone;Thynon;1,4-Dithiaanthraquinone-2,3-dicarbonitrile;2,3-Dinitrilo-1,4-dithia-9,10-anthraquinone;Delan;Delan-Col;Delan 75SC;NSC 218452;Delan WG;Delan 700WG;95591-89-2;11096-35-8;1135443-33-2

  • Categories:

    Agrochemicals  >  Fungicides

Description

Dithianon is a broad-spectrum anthraquinone fungicide with good adherence to the surface of leaves and fruits. Dithianon is used to control several several fungal of some fruits and vegetables, as anthracnose (Colletotrichum sp., Elsinoe ampelina), mildew (Plasmopara viticola), phomopsis (Phomopsis viticola), among others[1][2].


Solid


Dithianon is a naphthodithiin that is 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin which is substituted by nitrile groups at positions 2 and 3. It is a broad spectrum fungicide used to control scab, downy mildew, rust, and leaf spot in the commercial growing of grapes and other fruit, citrus, coffee, and vegetables. It has a role as an antifungal agrochemical. It is a naphthodithiin, a dinitrile and a member of p-quinones.

Dithianon Basic Attributes

296.32

296.32

222-098-6

3ESS44NI1F

218452

DTXSID8040270

Dark brown crystals, with a coppery luster|BROWN CRYSTALS

29349990

Characteristics

132

2.84

Solid

1.55 g/cm3 @ Temp: 18 °C

220 °C

402.1±45.0 °C at 760 mmHg

Ignition temperature >300 deg C

1.776

In water, 0.14 mg/L at 20 deg C

0-6°C

2.03X10-11 mm Hg at 25 deg C

LD50 orally in rats, guinea pigs: 638, 110 mg/kg (Amadori, Heupt)

Odorless

Henry's Law constant = 5.7X10-11 atm-cu m/mol at 25 °C (est)

Soluble in water approx 0.05 ppm at room temp; light brown color /Technical product/|Decomposed by alkaline media, by concentrated acids, and by prolonged heating; DT50 12.2 hr (pH 7, 25 °C).|Hydroxyl radical reaction rate constant = 2.0X10-11 cu cm/molecule-sec at 25 °C (est)|Ozone reaction rate constant = 1.8X10-18 cu cm/molecule-sec at 25 °C (est)|Light brown color. Melting point 230 °C. Solubility varies in organic solvents /Technical/

Noncorrosive

Safety Information

III

6.1(b)

UN 3077

3

22-50/53

24-60-61

QL0700000

Xn;N,N,Xn

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

P273-P501

H302-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.|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.

Incompatible with petroleum oils, alkaline materials, and sulfur-containing compounds.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P284, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 333 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P314, P321, P330, P333+P313, P337+P313, P363, and P501

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.

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.

Under some conditions ... /dithianon/ may cause severe skin irritation in sensitive individuals.

Toxicity

LD50 Rat oral 638 mg/kg|LD50 Guinea pig oral 110 mg/kg|LD50 Rat percutaneous >2000 mg/kg|LD50 Mouse oral 1140 mg/kg|For more Non-Human Toxicity Values (Complete) data for DITHIANON (6 total), please visit the HSDB record page.

/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.

Registration 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).

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).

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).

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 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).

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).

Occupational exposure and general population exposure should be low or non-existent since dithianon is no longer produced or used in the US (October, 1989). (SRC)

Drug Information

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)

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/ 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.

1,4-dithiaanthraquinone-2,3-dicarbonitrile

Dithianon Use and Manufacturing

Methods of Manufacturing

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

Uses

Fungicide.

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.

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.

The determination of dithianon in delan-col by a simple & specific spectrophotometric method based on reaction between carbonyl groups of dithianon & 2,4-dinitrophenylhydrazine is described.|Dithianon was detected in technical products & formulations by UV spectrophotometry. Residues of dithianon in fruit, cereals, & in water were detected with florisil column chromatography. Detection limit was approx 0.1 ppm; recoveries were 70-80%.|Residues may be determined by a colorimetric measurement.|Residue analysis for dithianon was carried out on 11 crops. For a 50 g sample, detection limits were 0.01 ppm; detected photometrically at 375 nm.|For more Analytic Laboratory Methods (Complete) data for DITHIANON (6 total), please visit the HSDB record page.

Agrochemicals -> Fungicides|Fungicides|Environmental transformation -> Pesticides (parent, predecessor)|FUNGICIDES

Dithianon has known environmental transformation products that include 1,2-Benzenedimethanol, D15 (CL902200), D3 (CL902195), D4 (CL 66629), D5 (4,11-dithia-2-aza-cyclopenta[b]anthracene-1,3,5,10-tetraone), D8 (CL902198), Dithianon ROI 10, Dithianon ROI 4(2), Dithianon ROI 4a, Dithianon ROI 4b, Dithianon ROI 8, Dithianon ROI 8(2), Dithianon metabolite NQ, Phthalaldehyde, and Phthalic acid.

Computed Properties

Molecular Weight:296.3
XLogP3:2.8
Hydrogen Bond Acceptor Count:6
Exact Mass:295.97141972
Monoisotopic Mass:295.97141972
Topological Polar Surface Area:132
Heavy Atom Count:20
Complexity:629
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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