Sedaxane

Source: Wikipedia, the free encyclopedia.
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 Edit this at Wikidata
UNII
  • InChI=1S/C18H19F2N3O/c1-23-9-14(16(22-23)17(19)20)18(24)21-15-5-3-2-4-11(15)13-8-12(13)10-6-7-10/h2-5,9-10,12-13,17H,6-8H2,1H3,(H,21,24)
    Key: XQJQCBDIXRIYRP-UHFFFAOYSA-N
  • CN1C=C(C(=N1)C(F)F)C(=O)NC2=CC=CC=C2C3CC3C4CC4
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

aryl amine to give an inhibitor of succinate dehydrogenase.[1][2]

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

basidiomycetes and was used as a seed treatment.[3][4] By 2016, at least 17 further examples of this mechanism of action were developed by crop protection companies, with the market leader being boscalid, owing to its broader spectrum of fungal species controlled. However, it lacked full control of important cereal diseases, especially septoria leaf blotch Zymoseptoria tritici.[3]

Pyrazole intermediate

A group of compounds which did control septoria were

Synthesis

Sedaxane combines the

2-chlorobenzaldehyde
.

px=500

A base-catalysed

α,β-unsaturated carbonyl compound which, when combined with hydrazine gives a dihydropyrazole derivative. Further treatment with potassium hydroxide forms the second cyclopropyl ring and this material is converted to the aniline required for sedaxane formation by Buchwald–Hartwig amination using benzophenone imine in the presence of a palladium catalyst, followed by hydroxylamine.[3]: 413–4 [7]

Owing to a lack of

enantiomers which are cis–trans isomers.[1]: 1828 [3]: 414  The commercial product consists of >80% of the trans isomers.[8]

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 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

active ingredients as seed treatments.[13][14]

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

  1. ^ a b c d William Donovan. "Sedaxane" (PDF). United States Environmental Protection Agency.
  2. PMID 23044852
    .
  3. ^ .
  4. ^ "History of SDHI-fungicides". frac.info. Retrieved 2023-07-26.
  5. ^ "Pyrazolecarboxamide fungicides". BCPC. Retrieved 2023-07-27.
  6. S2CID 103548298
    .
  7. ^ WO patent 2003074491, Ehrenfreund, J; Tobler, H & Walter, H, "O-cyclopropyl-carboxanilides and their use as fungicides", published 2003-09-12, assigned to Syngenta 
  8. ^ a b c d Pesticide Properties Database (2023-08-01). "Sedaxane". University of Hertfordshire. Retrieved 2023-08-03.
  9. PMID 14672929
    .
  10. .
  11. ^ FAO / WHO. "Sedaxane". Retrieved 2023-08-03.
  12. ^ "Fungicides Resistance Action Committee website".
  13. ^ "Search Fungicides to find FRAC Recommendations". Fungicides Resistance Action Committee. Retrieved 2023-08-03.
  14. ^ a b "Vibrance". Syngenta Australia. 2023. Retrieved 2023-08-03.
  15. ^ "Compendium of Pesticide Common Names: Sedaxane". BCPC. Retrieved 2023-08-03.