| Identification | Back Directory | [Name]
TRIAZOXIDE | [CAS]
72459-58-6 | [Synonyms]
brio
RAXIL S
TRIAZOXID
riazoxide
TRIAZOXIDE
GAUCHO ORGE
Triazoxide 0.1
TRIAZOXID PESTANAL
3-NITROPHENOL PESTANAL, 250 MG
7-chloro-3-(1H-imidazol-1-yl)-1,2,4-benzotriazine 1-oxide | [EINECS(EC#)]
276-668-4 | [Molecular Formula]
C10H6ClN5O | [MDL Number]
MFCD00145438 | [MOL File]
72459-58-6.mol | [Molecular Weight]
247.64 |
| Chemical Properties | Back Directory | [Melting point ]
178-182 °C | [Boiling point ]
533.4±42.0 °C(Predicted) | [density ]
1?+-.0.1 g/cm3(Predicted) | [vapor pressure ]
1 x 10-7 Pa (20 °C) | [Fp ]
>100 °C | [storage temp. ]
2-8°C | [form ]
neat | [pka]
-0.16±0.10(Predicted) | [Water Solubility ]
34 mg l-1 (20 °C) | [BRN ]
617803 | [Henry's Law Constant]
4.6×105 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) | [Major Application]
agriculture
environmental | [InChI]
1S/C10H6ClN5O/c11-7-1-2-8-9(5-7)16(17)14-10(13-8)15-4-3-12-6-15/h1-6H | [InChIKey]
IQGKIPDJXCAMSM-UHFFFAOYSA-N | [SMILES]
[O-][n+]1nc(nc2ccc(Cl)cc12)-n3ccnc3 | [EPA Substance Registry System]
1,2,4-Benzotriazine, 7-chloro-3-(1H-imidazol-1-yl)-, 1-oxide (72459-58-6) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
23/25 | [Safety Statements ]
45 | [RIDADR ]
UN2811 6.1/PG 1 | [WGK Germany ]
3 | [HS Code ]
29333990 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Inhalation
Acute Tox. 3 Oral | [Toxicity]
LD50 in rats (mg/kg): >5000 dermally; 100-200 orally; LC50 (4hr) in rats (mg/l): 0.8-3.2 by inhalation (Dutzmann) |
| Hazard Information | Back Directory | [Uses]
Fungicide. | [Uses]
Triazoxide is a pesticide. | [Uses]
Triazoxide is used as a seed dressing for the control of seed-borne
diseases in winter and spring barley. | [Definition]
ChEBI: A member of the class of benzotriazines that is 1,2,4-benzotriazine 1-oxide which is substituted by chlorine at position 7 and by a 1H-imidazol-1-yl group at position 3. A fungicide, it is used as a seed treatment for control of seed-bor
e Pyrenophora graminea and Pyrenophora teres in barley. | [Production Methods]
Triazoxide is commercially produced through a specialised synthesis involving benzotriazine and imidazole chemistry. The usual industrial synthesis begins with the preparation of a chlorinated benzotriazine core, which is then reacted with imidazole to introduce the heterocyclic substituent. This step is followed by oxidation to form the N-oxide functional group, which is critical for its fungicidal activity. | [Mechanism of action]
Specific, non-systemic. Exact mode of action is unclear but thought to be via the inhibition of fungal sterol synthesis leading to the disruption of cell membrane development and so fungal growth | [Metabolic pathway]
Triazoxide was the subject of an evaluation by the Pesticide Safety
Directorate of UK MAFF. The information presented below was obtained
from this source (PSD, 1994). The specific use of triazoxide (seed treatment)
gives rise to very low residues and therefore the metabolic pathways
in plants were not investigated. The compound is rather persistent
in soils and sediments but it is likely to be short-lived in water owing to
photolysis. Much is known about the absorption, distribution and elimination
of the compound in rat but only one metabolite, of apparently
many, was identified. The use pattern and consequent negligible residues
in plants did not warrant studies in nuninants and poultry. | [Degradation]
Triazoxide is very stable in water with extrapolated DT50 values of well
over 1 year at pH 4 and 7, and 23 days at pH 9. Aqueous photolysis is
expected to be more important under environmental conditions; the DT50
was 2-14 days at latitude 50" depending on the season. On a silica surface,
triazoxide was 95% degraded in 7 days when irradiated with a fluorescent
lamp. Details of the products were not reported. | [Pesticide Type]
Fungicide |
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