Dithianon

Modify Date: 2024-01-02 15:52:14

Dithianon Structure
Dithianon structure
Common Name Dithianon
CAS Number 3347-22-6 Molecular Weight 296.324
Density 1.7±0.1 g/cm3 Boiling Point 402.1±45.0 °C at 760 mmHg
Molecular Formula C14H4N2O2S2 Melting Point 220ºC
MSDS Chinese USA Flash Point 197.0±28.7 °C
Symbol GHS07 GHS09
GHS07, GHS09
Signal Word Warning

 Use of Dithianon


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].

 Names

Name dithianon
Synonym More Synonyms

 Dithianon 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
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

 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
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)

 Articles14

More 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...

 Synonyms

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