Sulfentrazone

Last updated
Sulfentrazone
Sulfentrazone.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
MeSH C475571
PubChem CID
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 Yes check.svgY
    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:
GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
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.

Contents

History

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

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

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

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]

Related Research Articles

<span class="mw-page-title-main">Herbicide</span> Chemical used to kill unwanted plants

Herbicides, also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds. Selective herbicides control specific weed species, while leaving the desired crop relatively unharmed, while non-selective herbicides can be used to clear waste ground, industrial and construction sites, railways and railway embankments as they kill all plant material with which they come into contact. Apart from selective/non-selective, other important distinctions include persistence, means of uptake, and mechanism of action. Historically, products such as common salt and other metal salts were used as herbicides, however these have gradually fallen out of favor and in some countries a number of these are banned due to their persistence in soil, and toxicity and groundwater contamination concerns. Herbicides have also been used in warfare and conflict.

<span class="mw-page-title-main">Diquat</span> Chemical compound

Diquat is the ISO common name for an organic dication that, as a salt with counterions such as bromide or chloride is used as a contact herbicide that produces desiccation and defoliation. Diquat is no longer approved for use in the European Union, although its registration in many other countries including the USA is still valid.

<span class="mw-page-title-main">Chlortoluron</span> Chemical compound

Chlortoluron or chlorotoluron are the common names for an organic compound of the phenylurea class of herbicides used to control broadleaf and annual grass weeds in cereal crops.

<span class="mw-page-title-main">Phenoxy herbicide</span>

Phenoxy herbicides are two families of chemicals that have been developed as commercially important herbicides, widely used in agriculture. They share the part structure of phenoxyacetic acid.

<span class="mw-page-title-main">Glufosinate</span> Broad-spectrum herbicide

Glufosinate is a naturally occurring broad-spectrum herbicide produced by several species of Streptomyces soil bacteria. Glufosinate is a non-selective, contact herbicide, with some systemic action. Plants may also metabolize bialaphos, another naturally occurring herbicide, directly into glufosinate. The compound irreversibly inhibits glutamine synthetase, an enzyme necessary for the production of glutamine and for ammonia detoxification, giving it antibacterial, antifungal and herbicidal properties. Application of glufosinate to plants leads to reduced glutamine and elevated ammonia levels in tissues, halting photosynthesis and resulting in plant death.

<span class="mw-page-title-main">Protoporphyrinogen oxidase</span>

Protoporphyrinogen oxidase or protox is an enzyme that in humans is encoded by the PPOX gene.

A mode of action (MoA) describes a functional or anatomical change, resulting from the exposure of a living organism to a substance. In comparison, a mechanism of action (MOA) describes such changes at the molecular level.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

Dicamba is a broad-spectrum herbicide first registered in 1967. Brand names for formulations of this herbicide include Dianat, Banvel, Diablo, Oracle and Vanquish. This chemical compound is a chlorinated derivative of o-anisic acid.

<span class="mw-page-title-main">Saflufenacil</span> Chemical compound

Saflufenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf weeds in crops including soybeans and corn.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

Mesotrione is the ISO common name for an organic compound that is used as a selective herbicide, especially in maize. A synthetic inspired by the natural substance leptospermone, it inhibits the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) and is sold under brand names including Callisto and Tenacity. It was first marketed by Syngenta in 2001.

<span class="mw-page-title-main">Acifluorfen</span> Chemical compound

Acifluorfen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to acifluorfen and its salts, via metabolic disposal by glutathione S-transferase. It is effective against broadleaf weeds and grasses and is used agriculturally on fields growing soybeans, peanuts, peas, and rice.

4-Hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors are a class of herbicides that prevent growth in plants by blocking 4-Hydroxyphenylpyruvate dioxygenase, an enzyme in plants that breaks down the amino acid tyrosine into molecules that are then used by plants to create other molecules that plants need. This process of breakdown, or catabolism, and making new molecules from the results, or biosynthesis, is something all living things do. HPPD inhibitors were first brought to market in 1980, although their mechanism of action was not understood until the late 1990s. They were originally used primarily in Japan in rice production, but since the late 1990s have been used in Europe and North America for corn, soybeans, and cereals, and since the 2000s have become more important as weeds have become resistant to glyphosate and other herbicides. Genetically modified crops are under development that include resistance to HPPD inhibitors. There is a pharmaceutical drug on the market, nitisinone, that was originally under development as an herbicide as a member of this class, and is used to treat an orphan disease, type I tyrosinemia.

<span class="mw-page-title-main">Bifenox</span> Chemical compound

Bifenox is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis.

<span class="mw-page-title-main">Cyanazine</span> Chemical compound

Cyanazine is a herbicide that belongs to the group of triazines. Cyanazine inhibits photosynthesis and is therefore used as a herbicide.

<span class="mw-page-title-main">Fomesafen</span> Herbicide

Fomesafen is the ISO common name for an organic compound used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase which is necessary for chlorophyll synthesis. Soybeans naturally have a high tolerance to fomesafen, via metabolic disposal by glutathione S-transferase. As a result, soy is the most common crop treated with fomesafen, followed by other beans and a few other crop types. It is not safe for maize/corn or other Poaceae.

<span class="mw-page-title-main">Fluazifop</span> ACCase herbicide, fop, anti-grass

Fluazifop is the ISO common name for an organic compound that is used as a selective herbicide. The active ingredient is the 2R enantiomer at its chiral centre and this material is known as fluazifop-P when used in that form. More commonly, it is sold as its butyl ester, fluazifop-P butyl with the brand name Fusilade.

<span class="mw-page-title-main">Indaziflam</span> Preemergent herbicide discovered in 2009

Indaziflam is a preemergent herbicide especially for grass control in tree and bush crops.

<span class="mw-page-title-main">Butafenacil</span> Chemical compound

Butafenacil is the ISO common name for an organic compound of the pyrimidinedione chemical class used as an herbicide. It acts by inhibiting the enzyme protoporphyrinogen oxidase to control broadleaf and some grass weeds in crops including cereals and canola.

<span class="mw-page-title-main">Aclonifen</span> Chemical compound

Aclonifen is a diphenyl ether herbicide which has been used in agriculture since the 1980s. Its mode of action has been uncertain, with evidence suggesting it might interfere with carotenoid biosynthesis or inhibit the enzyme protoporphyrinogen oxidase (PPO). Both mechanisms could result in the observed whole-plant effect of bleaching and the compound includes chemical features that are known to result in PPO effects, as seen with acifluorfen, for example. In 2020, further research revealed that aclonifen has a different and novel mode of action, targeting solanesyl diphosphate synthase which would also cause bleaching.

<span class="mw-page-title-main">Chlorsulfuron</span> ALS inhibitor herbicide

Chlorsulfuron is an ALS inhibitor herbicide, and is a sulfonylurea compound. It was discovered by George Levitt in February 1976 while working at DuPont, which was the patent assignee.

References

  1. 1 2 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. 1 2 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. USpatent 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.