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Sulfentrazone

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Sulfentrazone
Names
Preferred IUPAC name
N-{2,4-Dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]phenyl}methanesulfonamide
Other names
FMC97285, F6285
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.109.173 Edit this at Wikidata
KEGG
MeSH C475571
UNII
  • InChI=1S/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3 checkY
    Key: OORLZFUTLGXMEF-UHFFFAOYSA-N
  • InChI=1/C11H10Cl2F2N4O3S/c1-5-16-19(11(20)18(5)10(14)15)9-4-8(17-23(2,21)22)6(12)3-7(9)13/h3-4,10,17H,1-2H3
    Key: OORLZFUTLGXMEF-UHFFFAOYAF
  • CC1=NN(C(=O)N1C(F)F)C2=C(C=C(C(=C2)NS(=O)(=O)C)Cl)Cl
Properties[1]
C11H10Cl2F2N4O3S
Molar mass 387.190
Density 0.53 g/cm3
Melting point 122 °C (252 °F; 395 K)
780 mg/L (20 °C)
log P 0.991
Acidity (pKa) 6.56
Hazards[2]
GHS labelling:
GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
Warning
H332, H373, H411
P260, P261, P271, P273, P304+P312, P304+P340, P312, P314, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sulfentrazone is the ISO common name[3] for an organic compound used as a broad-spectrum herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase.[4] It was first marketed in the US in 1997 by FMC Corporation with the brand name Authority.

History

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In 1985, scientists at FMC Corporation filed patents on a new class of herbicides containing a triazolinone ring.[5] Sulfentrazone was subsequently developed for market under the code number F6285, with first sales in 1991[6] and achieving registration in the US in 1997, branded Authority.[7] Other compounds now in the triazolinone class include amicarbazone and carfentrazone.[8]

Mechanism of action

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The effects visible on whole plants are chlorosis and desiccation caused by the inhibition of the enzyme protoporphyrinogen oxidase, which leads to an accumulation of protoporphyrin IX in the plant cells. This is a potent photosensitizer which activates oxygen, leading to lipid peroxidation. Both light and oxygen are required for this process to kill the plant.[4][9]

Usage

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In the United States, the Environmental Protection Agency (EPA) is responsible for regulating pesticides under the Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA), the Food Quality Protection Act (FQPA) and the Pesticide Registration Improvement Act (PRIA). A pesticide can only be used legally according to the directions on the label that is included at the time of the sale of the pesticide. The purpose of the label is "to provide clear directions for effective product performance while minimizing risks to human health and the environment". A label is a legally binding document that mandates how the pesticide can and must be used and failure to follow the label as written when using the pesticide is a federal offence.[10][11]

The label includes use for removal of sedges and newly emerged broadleaf weeds including purple and yellow nutsedge, Kyllinga, plantain, clover, spurge, woodsorrel, knotweed, chickweed, curly dock, wild onion, and wild garlic. It is also effective on many grasses including Poa annua, Poa trivialis, creeping bentgrass, fine & tall fescue, perennial ryegrass, Kentucky & rough bluegrass, bahiagrass, Bermuda grass, buffalograss, carpetgrass, centipedegrass, kikuyugrass, seashore paspalum, St. Augustine grass, and zoysiagrass.

Sulfentrazone can be used both pre- and post-emergence and is rapidly metabolised by soybean at the methyl group of the triazolinone ring, which confers a level of safety to that crop.[12]

The estimated annual use of sulfentrazone in US agriculture is mapped by the US Geological Service and shows that in 2017, the latest date for which figures are available, approximately 3,800,000 pounds (1,700,000 kg) were applied — mainly in soybean.[13] The compound is not registered for use in the European Union, although another triazolinone, carfentrazone-ethyl, is available there.[14] Sulfentrazone also has uses outside agriculture: it controls vegetation on roadside verges and railroads.[15][16] The active ingredient has been sold alone or in combination with other herbicides under a large number of brand names including Dismiss, Solitaire and Spartan. Suppliers and brand names in the United States are listed in the National Pesticide Information Retrieval System.[17]

Human safety

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The LD50 of sulfentrazone is more than 2800 mg/kg (rats, oral), which means that it is of low toxicity by oral ingestion.[1] The US Code of Federal Regulations records the maximum residue tolerances in various food products.[18]

References

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  1. ^ a b Pesticide Properties Database. "Sulfentrazone". University of Hertfordshire. Retrieved 2021-04-19.
  2. ^ "Sulfentrazone". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-04-12.
  3. ^ "Compendium of Pesticide Common Names: sulfentrazone". BCPC.
  4. ^ a b Dayan, Franck E.; Duke, Stephen O. (2010). "Protoporphyrinogen Oxidase-Inhibiting Herbicides". Hayes' Handbook of Pesticide Toxicology. pp. 1733–1751. doi:10.1016/B978-0-12-374367-1.00081-1. ISBN 9780123743671.
  5. ^ US patent 4818275, Theodoridis, George, "Herbicidal aryl triazolinones", issued 1989-04-04, assigned to FMC Corporation 
  6. ^ Theodoridis, George; Baum, Jonathan S.; Hotzman, Frederick W.; Manfredi, Mark C.; Maravetz, Lester L.; Lyga, John W.; Tymonko, John M.; Wilson, Kenneth R.; Poss, Kathleen M.; Wyle, Michael J. (1992). "Synthesis and Herbicidal Properties of Aryltriazolinones". Synthesis and Chemistry of Agrochemicals III. ACS Symposium Series. Vol. 504. pp. 134–146. doi:10.1021/bk-1992-0504.ch014. ISBN 9780841224735.
  7. ^ "Sulfentrazone Factsheet" (PDF). United States EPA. 1997-02-27. Retrieved 2021-04-19.
  8. ^ "triazolone herbicides". alanwood.net. Retrieved 2021-04-12.
  9. ^ Nagano, Eiki (1999). "Herbicidal Efficacy of Protoporphyrinogen Oxidase Inhibitors". Peroxidizing Herbicides. pp. 296–299. doi:10.1007/978-3-642-58633-0_11. ISBN 978-3-642-63674-5.
  10. ^ "About Pesticide Registration". US EPA. 27 February 2013. Retrieved 2021-04-19.
  11. ^ US EPA. "Sulfentrazone 4 Herbicide" (PDF). www3.epa.gov. Retrieved 2021-04-19.
  12. ^ Dayan, F.; Weete, J.; Duke, S.; Hancock, H. (1997). "Soybean (Glycine max) cultivar differences in response to sulfentrazone". Weed Science. 45 (5): 634–641. JSTOR 4045886.
  13. ^ US Geological Survey. "Estimated Agricultural Use for Sulfentrazone, 2017". Retrieved 2021-04-19.
  14. ^ Pesticide Properties Database. "Carfentrazone-ethyl". University of Hertfordshire. Retrieved 2021-04-19.
  15. ^ "Sulfentrazone: Roadside Vegetation Management" (PDF). Washington State DOT. 2017. Retrieved 2021-04-19.
  16. ^ "Sulfentrazone ROW herbicide" (PDF). US EPA label. 2020-04-17. Retrieved 2021-04-19.
  17. ^ NPIRS Public. "Search Federal Pesticide Products".
  18. ^ "Sulfentrazone; tolerances for residues". ecfr.federalregister.gov. 1997-03-10. Retrieved 2021-04-19.
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