| Identification | More | [Name]
Fenaminosulf | [CAS]
140-56-7 | [Synonyms]
4-DIMETHYLAMINOBENZENEDIAZOSULFONIC ACID SODIUM SALT
4-DIMETHYLAMINOPHENYLDIAZOSULFONIC ACID SODIUM SALT
BAYER 22555
DAPA
Dexon
DEXON (TM)
Dexoxon
Diazoben
FENAMINOSULF
P-DIMETHYLAMINOBENZENEDIAZO-SULFONIC ACID, SODIUM SALT
SODIUM 4-DIMETHYLAMINOBENZENEDIAZOSULFONATE
SODIUM 4-DIMETHYLAMINOBENZENEDIAZO SULPHONATE
Sodium p(dimethylamino)benzenediazo sulfonate
(4-(dimethylamino)phenyl)diazenesulfonicacid,sodiumsalt
(4-(dimethylamino)phenyl)-diazenesulfonicacisodiumsalt
4-((dimethylamino)phenyl)diazenesulfonicacid,sodiumsalt
4-((dimethylamino)phenyl)diazenesulphonicacid,sodiumsalt
4-(dimethylamino)phenyl)diazenesulfonate
4-dimethylaminobenzenediazosulfonic*acidsodium
4-dimethylaminobenzenediazosulphonicacid,sodiumsalt | [EINECS(EC#)]
205-419-4 | [Molecular Formula]
C8H10N3NaO3S | [MDL Number]
MFCD00059900 | [Molecular Weight]
251.24 | [MOL File]
140-56-7.mol |
| Chemical Properties | Back Directory | [storage temp. ]
−20°C
| [solubility ]
DMSO (Slightly), Methanol (Slightly) | [Water Solubility ]
Slightly soluble in water | [form ]
neat | [color ]
Light yellow to Brown | [BRN ]
4170376 | [Stability:]
Hygroscopic | [Major Application]
agriculture
environmental | [InChI]
1S/C8H11N3O3S.Na/c1-11(2)8-5-3-7(4-6-8)9-10-15(12,13)14;/h3-6H,1-2H3,(H,12,13,14);/q;+1/p-1 | [InChIKey]
IWDQPCIQCXRBQP-UHFFFAOYSA-M | [SMILES]
[Na+].CN(C)c1ccc(cc1)N=NS([O-])(=O)=O | [CAS DataBase Reference]
140-56-7(CAS DataBase Reference) | [IARC]
3 (Vol. 8, Sup 7) 1987 | [EPA Substance Registry System]
140-56-7(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301-H312-H412 | [Precautionary statements ]
P273-P280-P301+P310+P330-P302+P352+P312 | [Hazard Codes ]
T | [Risk Statements ]
R21:Harmful in contact with skin.
R25:Toxic if swallowed.
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
CZ1750000
| [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29270000 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Acute Tox. 4 Dermal
Aquatic Chronic 3 | [Safety Profile]
Poison by ingestion,
intravenous, and intraperitoneal routes.
Experimental teratogenic effects. Human
mutation data reported. Questionable
carcinogen, A fungicide. When heated to
decomposition it emits very toxic fumes of
NOx, Na2O, and SOx | [Hazardous Substances Data]
140-56-7(Hazardous Substances Data) | [Toxicity]
bird - wild,LD50,oral,18mg/kg (18mg/kg),Toxicology and Applied Pharmacology. Vol. 21, Pg. 315, 1972. |
| Hazard Information | Back Directory | [General Description]
Yellow-brown crystals or brown powder. | [Reactivity Profile]
Aqueous solutions are sensitive to exposure to light. | [Air & Water Reactions]
Dust may form an explosive mixture in air. Water soluble. | [Fire Hazard]
Flash point data are not available for this compound. FORMULATED FENAMINOSULF is probably combustible. | [Description]
Introduced in 1955, fenaminosulf (1; Lesan; Dexon)
was one of the first selective, systemic fungicides.
It is active against Phycomycetes such as Pythium,
Phytophthora, and Aphanomyces but has little or no
effect on higher fungi belonging to the Ascomycetes or
Basidiomycetes. Fenaminosulf has a relatively high water
solubility (20,000 mgL-1), a feature often associated
with fungicides that specifically inhibit Oomycetes (3).
Another important physicochemical property is photolytic
instability, one of the reasons that fenaminosulf was
developed as a seed dressing and soil fungicide (4).
As a consequence of acute toxicity , limited
spectrum, and photo-instability, the use of fenaminosulf
decreased (4), and it is now listed in The Pesticide
Manual (5) among products that have been superseded.
Although no longer used, it is included here for
completeness, being the only example of a commercial
fungicide that acts on complex I.
During its period of use, fenaminosulf, as wettable powder
(WP), dust, or granular formulations, was employed
as a seed dressing and soil-applied fungicide to control
damping off and foot/root rots. Fenaminosulf-based products
were used on a range of plants including vegetables,
field crops, ornamentals, and turf. | [Uses]
Used in biological and pharmacological studies including:• ;Cloning and characterization of GABA transporter1• ;Activity of anti-RSV carbonucleosides2• ;Inhibition by fungicides of urea hydrolysis and nitrification of urea nitrogen in soil3 | [Definition]
ChEBI: Fenaminosulf is an organic molecular entity. | [Production Methods]
The commercial production of fenaminosulf follows a concise two-step diazo coupling process. First, N,N-dimethylaniline is diazotised by adding sodium nitrite to a cold solution of the amine in dilute acid forming the diazonium chloride salt in situ under controlled pH. This diazonium salt is then coupled with sulphite ions (from sodium sulphite or bisulphite) in a buffered aqueous medium, where the electrophilic diazonium attacks the sulphite to yield the diazosulfonate anion, followed by neutralisation with sodium carbonate to precipitate or crystallise fenaminosulf. | [Mechanism of action]
Interferes with NADH-ubiquinone reductase (complex I). | [Pesticide Type]
Fungicide |
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