Pyrasulfotole

Pyrasulfotole
Names
IUPAC name
(5-Hydroxy-1,3-dimethylpyrazol-4-yl)(α,α,α-trifluoro-2-mesyl-p-tolyl)methanone
Other names
  • (5-Hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methanesulfonyl)-4-(trifluoromethyl)phenyl]methanone
  • (5-Hydroxy-1,3-dimethyl-1H-pyrazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)phenyl]methanone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.123.578
UNII
  • InChI=1S/C14H13F3N2O4S/c1-7-11(13(21)19(2)18-7)12(20)9-5-4-8(14(15,16)17)6-10(9)24(3,22)23/h4-6,21H,1-3H3
    Key: CZRVDACSCJKRFL-UHFFFAOYSA-N
  • CC1=C(C(=O)N(N1)C)C(=O)C2=C(C=C(C=C2)C(F)(F)F)S(=O)(=O)C
Properties
C14H13F3N2O4S
Molar mass 362.32 g·mol−1
Appearance Beige coloured powder[1]
Density 1.53 kg/L, 15.3 lb/gal Imp[1]
Melting point 201°C, 394°F[1]
69.1g/L[1]
Solubility in ethanol 21.6 g/L[1]
Solubility in toluene 6.9 g/L[1]
Solubility in acetone 89.2 g/L[1]
Solubility in ethyl acetate 37.2 g/L[1]
Vapor pressure 270 nPa (3.9 x10-11 psi)[1]
Hazards
GHS labelling:
GHS08: Health hazardGHS09: Environmental hazard
Warning
H373, H410
P260, P273, P319, P391, P501
Flash point 96°C, 205°F[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pyrasulfotole is a herbicide used to control broadleaf weeds in what and barley.[2] It is a selective benzoylpyrazolone,[3] pyrazole compound, registered in Canada and Australia in 2004, and the USA in 2007.[1] Bayer patented it in Australia in 2006, and the patent expired in March 2026.[3]

Application

Pyrasulfotole is generally sold as an emulsifiable concentrate of 75-230 g/L, or 37.5 g/L in a mixture with bromoxynil.[4][5][6][7][8]

Some pyrasulfotole formulations include mefenpyr-diethyl as a safener.[9] Bayer's patent also covers other safeners: cloquintocet-mexyl and 4-cyclopropylaminocarbonyl-N-(2-methoxybenzoyl)benzenesulfonamide.[3]

Mechanism

It acts by one mechanism of action, inhibition of 4-hydroxyphenylpyruvate dioxygenase (HPPD), placing it in the Group H (Australia), Group F2 (global), Group 27 (numeric) HRAC class.[8][10]

An APVMA report claims pyrasulfotole acts by two mechanisms of action: inhibiting "4-hydroxyphenylpyruvate deoxygenase" (sic) (HPPD) and disrupting plant cell growth, with a dual HRAC class of Groups F & I (Australia),[11][12] though inhibiting HPPD is the MoA of Group H (Group 27),[10] and as of 2026, pyrasulfotole is listed as only as Group H.[13]

Tradenames

Formulations of pyrasulfotole have been sold as Galaxy (Nufarm),[5] Marathon (ADAMA),[2] Precept (Bayer),[11] and Pyrasulfotole 80 (4Farmers),[6] and as an active ingredient in a mixture with bromoxynil as Pyra Brom (4Farmers),[8] and Velocity (Bayer).[4]

References

  1. 1 2 3 4 5 6 7 8 9 10 11 Tzilivakis, J., Lewis, K.A., Green, A. and Warner, D.J. (2026) A decade of growth and impact of the Pesticide Properties Database (PPDB). Human and Ecological Risk Assessment: An International Journal, 1–26. DOI: 10.1080/10807039.2026.2702066
  2. 1 2 Benson, Pesach (28 April 2026). "Israeli Firm ADAMA Launches New Herbicide in Australia". israel.com.
  3. 1 2 3 "Australian Patent No. 2006228738". ipsearch.ipaustralia.gov.au. IP Australia.
  4. 1 2 "Velocity® Selective Herbicide Label and SDS | Bayer Crop Science". www.crop.bayer.com.au. Retrieved 24 July 2026.
  5. 1 2 "Galaxy". Nufarm Australia.
  6. 1 2 "Gazette Agricultural and veterinary chemicals No. APVMA 9, 30 April 2024" (PDF). APVMA. Retrieved 24 July 2026.
  7. ↑ "Marathon Product Guide" (PDF). ADAMA. Retrieved 26 July 2026.
  8. 1 2 3 "4Farmers Pyra Brom". 4Farmers Australia. Retrieved 24 July 2026.
  9. ↑ "ADAMA Launches Marathon® in Australia, Its First Pyrasulfotole-Based Herbicide for Cereal Growers". Global Agriculture. 27 April 2026.
  10. 1 2 "Specific guidelines for Group 27 herbicides". CropLife Australia. 22 July 2026. Retrieved 24 July 2026.
  11. 1 2 "Evaluation of the new active pyrasulfotole in the product Precept Selective Herbicide" (PDF). Canberra, Australia: APVMA. Retrieved 24 July 2026.
  12. ↑ The APVMA report says "deoxygenase", which is here assumed to be a typo of "dioxygenase".
  13. ↑ "Herbicide Mode of Action Table". CropLife Australia. 22 July 2026. Retrieved 24 July 2026.
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