DITHIANON Chemical Properties

Melting point:

225°

Boiling point:

402.1±45.0 °C(Predicted)

Density 

d18 1.55

refractive index 

1.6360 (estimate)

storage temp. 

0-6°C

Water Solubility 

0.5mg/L(temperature not stated)

Merck 

13,3404

BRN 

1325563

Major Application

agriculture
environmental

InChI

1S/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

InChIKey

PYZSVQVRHDXQSL-UHFFFAOYSA-N

SMILES

O=C1C2=C(SC(C#N)=C(S2)C#N)C(=O)c3ccccc13

LogP

2.840

CAS DataBase Reference

3347-22-6(CAS DataBase Reference)

NIST Chemistry Reference

Dithianone(3347-22-6)

EPA Substance Registry System

Dithianon (3347-22-6)

Safety Information

Hazard Codes 

Xn;N,N,Xn

Risk Statements 

22-50/53

Safety Statements 

24-60-61

RIDADR 

UN 3077

WGK Germany 

3

RTECS 

QL0700000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29349990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Aquatic Acute 1
Aquatic Chronic 1

Hazardous Substances Data

3347-22-6(Hazardous Substances Data)

Toxicity

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

MSDS

• Language:English Provider:Dithiaanthraquinone-2,3-dinitrile

DITHIANON Usage And Synthesis

Description

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.

Uses

Fungicide.

Definition

ChEBI: 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 rowing of grapes and other fruit, citrus, coffee, and vegetables.

Agricultural Uses

Fungicide: Fungicide used to control certain mildews. A seed dressing; used to attack foliar diseases of fruits (pome, stone, etc,), coffeee, wine, and vegetables. Not currently registered for use in the U.S. Approved for use in most EU countries.

Trade name

DELAN®; DELAN-COL®; DELAN 70WG®; DITHIANON FLOWABLE®; DITHIANONWG®; IT 931®; MV 119A®; STAUFFER MV-119A®; THYNON®

Contact allergens

Dithianon is an anthraquinone derivative, used as a fungicide agent. With cymoxanil, it is contained in Aktuan. Cases in agricultural workers were reported sparsely.

Synthesis

Using sodium monophosphate disodium phosphate to prepare a buffer solution of pH 7 (prepared by adding 19.5 ml of 0.2 M dibasic sodium phosphate 30.5 ml / 0.2 M monobasic sodium phosphate in 500 ml of water) In 1.7 L of the solution, 60 g of diclones were dispersed using 3 g of a surfactant (polyethylene lauric acid), and the temperature was cooled to 10 ° C. 160.5 g of an aqueous solution of ethene salt (36% of ethene salt) is slowly added dropwise over 2 hours. After the addition was completed, the reaction was further performed for 1 hour, filtered at that temperature, washed with water, and dried to obtain 70.4 g (yield 90.0%, purity 93.5%) of dithianon.[1]

References

[1] Process for preparing high purity 2,3-dicyano-1,4-dithia anthraquinone. Patent No. KR100209582B1

DITHIANON(3347-22-6)Related Product Information

• Clothianidin
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• Fenobucarb
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• FLUTOLANIL
• Glycerol
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• BETA-CYPERMETHRIN
• Anthraquinone
• (ETHYLTHIO)ACETONE
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• 1,4-Naphthoquinone
• ETHYL VINYL SULFIDE
• DITHIANON
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• 2,3-BIS(METHYLTHIO)-1,4-NAPHTHALENEDIONE
• ALPHA-(ETHYLTHIO)ACETOPHENONE, 97