Dithianon

Names

[ Name ]:
Dithianon

[Synonym ]:
2,3-Dicyano-1,4-dithiaanthraquinone
Thynon
5,10-Dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiine-2,3-dicarbonitrile
Caswell No. 349B
Delan-col
5,10-dioxobenzo[g][1,4]benzodithiine-2,3-dicarbonitrile
Dithianon
Delan
5,10-dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithiine-2,3-dicarbonitrile
EINECS 222-098-6
DITHIANONE
MFCD00055492
Delan WP
Naphtho[2,3-b]-1,4-dithiin-2,3-dicarbonitrile, 5,10-dihydro-5,10-dioxo-
Stauffer MV 119A
Stauffer MV-119A
Merkdelan
2,3-dicyano-1,4-dithia-anthraquinone
5,10-Dihydro-5,10-dioxonaphtho[2,3-b]-1,4-dithiin-2,3-dicarbonitrile

Biological Activity

[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].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[Target]

Reactive oxygen species (ROS)[1] Colletotrichum sp.; Elsinoe ampelina; Plasmopara viticola; Phomopsis viticola[1]

[In Vitro]

When exponentially aerobic growing cells of S. cerevisiae are submitted to acute Dithianon treatment they loss cell wall and membrane integrity, dying by necrosis, and this behavior is associated to a depletion of reduced proteic and non-proteic thiol groups. An important increase of cellular reactive oxygen species (ROS) associated to mitochondrial membrane potential modifications on Dithianon treated cells are also detected[1]. In filamentous fungus, Dithianon inhibits mycelial growth and conidial germination. Studies on Ehrlich ascites carcinoma and yeast cells showed that Dithianon inhibits respiration and fermentation affecting several thiol enzymes of the glycolytic pathway as hexokinase, phosphofructokinase, and glyceraldeyde-3-phosphate dehydrogenase[1]. Dithianon has in vitro cytotoxic effect and affect cell transforming activity of BLAB/c 3 T3 cells[1].

[In Vivo]

The activity of testosterone hydroxylase of liver microsomes derived from male mice is increased when they are treated with acute doses of Dithianon, while in females an inactivating effect is observed[1].

[References]

[1]. Scariot FJ, et al. Necrotic cell death induced by dithianon on Saccharomyces cerevisiae. Pestic Biochem Physiol. 2018 Jul;149:137-142.

[2]. Halasz I, et al. Structures of four polymorphs of the pesticide dithianon solved from X-ray powder diffraction data. Acta Crystallogr B. 2012 Dec;68(Pt 6):661-6.

Chemical & Physical Properties

[ Density]:
1.7±0.1 g/cm3

[ Boiling Point ]:
402.1±45.0 °C at 760 mmHg

[ Melting Point ]:
220ºC

[ Molecular Formula ]:
C₁₄H₄N₂O₂S₂

[ Molecular Weight ]:
296.324

[ Flash Point ]:
197.0±28.7 °C

[ Exact Mass ]:
295.971405

[ PSA ]:
138.20000

[ LogP ]:
1.86

[ Vapour Pressure ]:
0.0±0.9 mmHg at 25°C

[ Index of Refraction ]:
1.776

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QL0700000

CHEMICAL NAME :: Naphtho(2,3-b)-p-dithiin-2,3-dicarbonitrile, 5,10-dihydro-5,10-dioxo-

CAS REGISTRY NUMBER :: 3347-22-6

BEILSTEIN REFERENCE NO. :: 1325563

LAST UPDATED :: 199710

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C14-H4-N2-O2-S2

MOLECULAR WEIGHT :: 296.32

WISWESSER LINE NOTATION :: T C666 BV DS GS IVJ ECN FCN

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 638 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3 gm/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1015 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1110 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 110 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - mouse Fibroblast

DOSE/DURATION :: 25 mg/L

REFERENCE :: EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 21,81,1993

Safety Information

[ Symbol ]:

GHS07, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H410

[ Precautionary Statements ]:
P273-P501

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R22;R50/53

[ Safety Phrases ]:
S24-S60-S61

[ RIDADR ]:
UN 3077

[ RTECS ]:
QL0700000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Articles

Effect of thiol blocking agents on the binding of T3 and T4 in rat liver nuclear extract.

Acta Endocrinol. 98(1) , 68-72, (1981)

Liver nuclei bind thyroid hormones (T3 and T4) with different binding affinities. In out studies it was estimated that the apparent association constant (Ka) in the liver nuclei for T3 was 8.8 X 10(10...

Identification of ABC transporter genes of Fusarium graminearum with roles in azole tolerance and/or virulence.

PLoS ONE 8 , e79042, (2013)

Fusarium graminearum is a plant pathogen infecting several important cereals, resulting in substantial yield losses and mycotoxin contamination of the grain. Triazole fungicides are used to control di...

In vitro cytotoxic and cell transforming activities exerted by the pesticides cyanazine, dithianon, diflubenzuron, procymidone, and vinclozolin on BALB/c 3T3 cells.

Environ. Mol. Mutagen. 21(1) , 81-6, (1993)

Cytotoxic and cell transforming activities of the pesticides cyanazine, diflubenzuron, dithianon, procymidone, and vinclozolin were investigated in vitro by utilizing the BALB/c 3T3 cell transformatio...