Sedaxane
Names | |
---|---|
Preferred IUPAC name
N-[2-([1,1′-Bi(cyclopropan)]-2-yl)phenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide | |
Other names
SYN524464
| |
Identifiers | |
3D model (
JSmol ) |
|
ChemSpider | |
ECHA InfoCard
|
100.214.982 |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties[1] | |
C18H19F2N3O | |
Molar mass | 331.367 g·mol−1 |
Appearance | White powder |
Odor | Odorless |
Density | 1.23 g/cm3 (26 °C) |
Melting point | 121.4 °C (250.5 °F; 394.5 K) |
Very slightly soluble (0.67 g/L, 20 °C) | |
Solubility in other solvents | Slightly soluble in acetone (410 g/L) and dichloromethane (500 g/L) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Sedaxane is a broad spectrum fungicide used as a
The compound is widely registered for use, including in Australia, the EU, UK and US.
History
Inhibition of succinate dehydrogenase, the complex II in the
A group of compounds which did control septoria were
Synthesis
Sedaxane combines the
A base-catalysed
Owing to a lack of
Mechanism of action
SDHI of this type act by binding at the quinone reduction site of the enzyme complex, preventing
Usage
Sedaxane is used as a seed treatment to control, for example, common bunt, Rhizoctonia species and Ustilago species (smuts). As a result, it has potential use in crops including cereals, cotton, potato and soybean. As of 2023[update] it is registered for use in Argentina, Australia, Canada, Chile, China, the EU, Mexico, the UK, Uruguay and the US.[8]
Human safety
Sedaxane has low toxicity[8] and its use was found to leave no residues in human food:[1] however the Codex Alimentarius database maintained by the FAO lists the maximum residue limits for it in various food products.[11]
Resistance management
Fungal populations have the ability to develop
Brands
Sedaxane is the ISO common name[15] for the active ingredient which is formulated into the branded product sold to end-users. Vibrance is the brand name for Syngenta's suspension concentrate.[14]
References
- ^ a b c d William Donovan. "Sedaxane" (PDF). United States Environmental Protection Agency.
- PMID 23044852.
- ^ ISBN 9783527339471.
- ^ "History of SDHI-fungicides". frac.info. Retrieved 2023-07-26.
- ^ "Pyrazolecarboxamide fungicides". BCPC. Retrieved 2023-07-27.
- S2CID 103548298.
- ^ WO patent 2003074491, Ehrenfreund, J; Tobler, H & Walter, H, "O-cyclopropyl-carboxanilides and their use as fungicides", published 2003-09-12, assigned to Syngenta
- ^ a b c d Pesticide Properties Database (2023-08-01). "Sedaxane". University of Hertfordshire. Retrieved 2023-08-03.
- PMID 14672929.
- .
- ^ FAO / WHO. "Sedaxane". Retrieved 2023-08-03.
- ^ "Fungicides Resistance Action Committee website".
- ^ "Search Fungicides to find FRAC Recommendations". Fungicides Resistance Action Committee. Retrieved 2023-08-03.
- ^ a b "Vibrance". Syngenta Australia. 2023. Retrieved 2023-08-03.
- ^ "Compendium of Pesticide Common Names: Sedaxane". BCPC. Retrieved 2023-08-03.