CAS Number3347-22-6
Synonyms2,3-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; 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
Molecular FormulaC14H4N2O2S2
Molecular Weight296.32
Purity98%
Density1.7±0.1 g/cm3
Boiling Point402.1±45.0 °C at 760 mmHg
Melting Point220ºC
AppearanceGray-brown needle-like, odorless
EINECS222-098-6
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 3347-22-6 |
| Catalog No. | 2A-9007633 |
| Chinese Name | 二氰蒽醌 |
| 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; 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 |
| Molecular Formula | C14H4N2O2S2 |
| Molecular Weight | 296.32 |
| Purity | 98 |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 402.1±45.0 °C at 760 mmHg |
| Melting Point | 220ºC |
| Appearance | Gray-brown needle-like, odorless |
| Storage Condition | Store at room temperature, away from light, in a v |
| Packaging | III |
| Application | Dithianon is a broad-spectrum anthraquinone fungicide with good adhesion to leaf and fruit surfaces. Dithianon is used to control several fungi on certain fruits and vegetables, such as Colletotrichum |
| EINECS | 222-098-6 |
| PubChem ID | 329756755 |
| MDL Number | MFCD00055492 |
| SMILES | O=C1C2=C(SC(C#N)=C(S2)C#N)C(=O)c3ccccc13 |
| 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 |
| InChI Key | PYZSVQVRHDXQSL-UHFFFAOYSA-N |
| Beilstein/REAXYS | 1325563 |
| NACRES Code | NA.24 |
| UNSPSC | 41116107 |
| Hazard Symbols | 6.1(b) |
| MSDS | msds/7633_2_3347_22_6.pdf |
| Bioactivity | 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 InChIKey PYZSVQVRHDXQSL-UHFFFAOYSA-N SMILES N#Cc1sc2c(=O)c3ccccc3c(=O)c=2sc1C#N Storage condition 0-6°C |
| Use of | 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]. Properties Articles14 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 Research Areas >> Infection Signaling Pathways >> Anti-infection >> Fungal Reactive oxygen species (ROS)[1] Colletotrichum sp.; Elsinoe ampelina; Plasmopara viticola; Phomopsis viticola[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 Molecular Formula C14H4N2O2S2 Exact Mass 295.971405 PSA 138.20000 Index of Refraction 1.776 InChIKey PYZSVQVRHDXQSL-UHFFFAOYSA-N |
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