Sulfentrazone: Difference between revisions

Sulfentrazone
Names
	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
CAS Number	122836-35-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:9339 ;
ChemSpider	77887 ;
ECHA InfoCard	100.109.173
KEGG	C11125;
MeSH	C475571
PubChem CID	86369;
UNII	7TY7WT1599 ;
CompTox Dashboard (EPA)	DTXSID6032645 ;
	InChI 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 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;
	SMILES CC1=NN(C(=O)N1C(F)F)C2=C(C=C(C(=C2)NS(=O)(=O)C)Cl)Cl;
Properties
Chemical formula	C11H10Cl2F2N4O3S
Molar mass	387.190
Density	0.53 g/cm3
Melting point	122 °C (252 °F; 395 K)
Solubility in water	780 mg/l (20 °C)
log P	0.991
Acidity (pKa)	6.56
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H332, H373, H411
Precautionary statements	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). Infobox references

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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

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]

References

^ ^a ^b Pesticide Properties Database. "Sulfentrazone". University of Hertfordshire. Retrieved 2021-04-19.
^ "Sulfentrazone". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-04-12.
^ "Compendium of Pesticide Common Names". alanwood.net.
^ ^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.
^ US patent 4818275, Theodoridis, George, "Herbicidal aryl triazolinones", issued 1989-04-04, assigned to FMC Corporation
^ 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.
^ "Sulfentrazone Factsheet" (PDF). United States EPA. 1997-02-27. Retrieved 2021-04-19.
^ "triazolone herbicides". alanwood.net. Retrieved 2021-04-12.
^ 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.
^ "About Pesticide Registration". US EPA. Retrieved 2021-04-19.
^ US EPA. "Sulfentrazone 4 Herbicide" (PDF). www3.epa.gov. Retrieved 2021-04-19.
^ Dayan, F.; Weete, J.; Duke, S.; Hancock, H. (1997). "Soybean (Glycine max) cultivar differences in response to sulfentrazone". Weed Science. 45 (5): 634–641.
^ US Geological Survey. "Estimated Agricultural Use for Sulfentrazone, 2017". Retrieved 2021-04-19.
^ Pesticide Properties Database. "Carfentrazone-ethyl". University of Hertfordshire. Retrieved 2021-04-19.
^ "Sulfentrazone: Roadside Vegetation Management" (PDF). Washington State DOT. 2017. Retrieved 2021-04-19.
^ "Sulfentrazone ROW herbicide" (PDF). US EPA label. 2020-04-17. Retrieved 2021-04-19.
^ NPIRS Public. "Search Federal Pesticide Products".
^ "Sulfentrazone; tolerances for residues". ecfr.federalregister.gov. 1997-03-10. Retrieved 2021-04-19.

External links

Sulfentrazone in the Pesticide Properties DataBase (PPDB)

[PPDB-1] Pesticide Properties Database. "Sulfentrazone". University of Hertfordshire. Retrieved 2021-04-19.

[pubchem-2] "Sulfentrazone". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-04-12.

[3] "Compendium of Pesticide Common Names". alanwood.net.

[Dayan-4] 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.

[US4818275-5] 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.

[epa.gov-10] "About Pesticide Registration". US EPA. Retrieved 2021-04-19.

[USlabel-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.

[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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@@ Line 1: / Line 1: @@
-{{Underlinked|date=June 2020}}
 {{chembox
 | ImageFile = Sulfentrazone.svg
 | ImageSize =
 | IUPACName = ''N''-<nowiki/>{2,4-Dichloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1''H''-1,2,4-triazol-1-yl]phenyl}methanesulfonamide
-| OtherNames =
+| OtherNames = FMC97285, F6285
 | Section1 = {{Chembox Identifiers
 | Abbreviations =
@@ Line 15: / Line 13: @@
 | PubChem = 86369
 | ChemSpiderID = 77887
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | SMILES = CC1=NN(C(=O)N1C(F)F)C2=C(C=C(C(=C2)NS(=O)(=O)C)Cl)Cl
 | 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
@@ Line 20: / Line 19: @@
 | StdInChI = 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
 | StdInChIKey = OORLZFUTLGXMEF-UHFFFAOYSA-N
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | RTECS =
 | MeSHName = C475571
 | ChEBI = 9339
+| ChEBI_Ref = {{ebicite|correct|EBI}}
 | KEGG = C11125
   }}
 | Section2 = {{Chembox Properties
+| Properties_ref = <ref name=PPDB>{{cite web |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/601.htm |title=Sulfentrazone |publisher=University of Hertfordshire |author=Pesticide Properties Database |access-date=2021-04-19}}</ref>
 | Formula = C<sub>11</sub>H<sub>10</sub>Cl<sub>2</sub>F<sub>2</sub>N<sub>4</sub>O<sub>3</sub>S
 | MolarMass = 387.190
 | Appearance =
 | Density = 0.53 g/cm<sup>3</sup>
+| MeltingPtC = 122
-| MeltingPt = 121-123 °C
 | MeltingPt_notes =
 | BoilingPt =
 | BoilingPt_notes =
-| Solubility =
+| Solubility = 780 mg/l (20&nbsp;°C)
 | SolubleOther =
 | Solvent =
-| pKa =
+| pKa = 6.56
 | pKb =
+| LogP = 0.991
   }}
 | Section7 = {{Chembox Hazards
+| Hazards_ref=<ref name=pubchem >{{cite web |url=https://pubchem.ncbi.nlm.nih.gov/compound/86369 |website=pubchem.ncbi.nlm.nih.gov |title=Sulfentrazone |access-date=2021-04-12}}</ref>
 | ExternalSDS =
 | EUClass =
+| GHSPictograms =  {{GHS07}}{{GHS08}}{{GHS09}}
-| MainHazards =
+| GHSSignalWord = Warning
-| NFPA-H =
+| HPhrases = {{H-phrases|332|373|411}}
-| NFPA-F =
+| PPhrases = {{P-phrases|260|261|271|273|304+312|304+340|312|314|391|501}}
-| NFPA-R =
-| NFPA-S =
-| RPhrases =
-| SPhrases =
-| RSPhrases =
-| FlashPt =
-| AutoignitionPt =
-| ExploLimits =
-| PEL =
   }}
 }}
+'''Sulfentrazone''' is the [[International Organization for Standardization|ISO]] [[trivial name|common name]]<ref>{{cite web |url=http://www.alanwood.net/pesticides/ |title=Compendium of Pesticide Common Names|website=alanwood.net}}</ref> for an [[organic compound]] used as a broad-spectrum [[herbicide]]. It acts by [[enzyme inhibitor|inhibiting the enzyme]] [[protoporphyrinogen oxidase]].<ref name=Dayan>{{cite book |doi=10.1016/B978-0-12-374367-1.00081-1 |chapter=Protoporphyrinogen Oxidase-Inhibiting Herbicides |title=Hayes' Handbook of Pesticide Toxicology |year=2010 |last1=Dayan |first1=Franck E. |last2=Duke |first2=Stephen O. |pages=1733–1751 |isbn=9780123743671 }}</ref> It was first marketed in the US in 1997 by [[FMC Corporation]] with the [[brand name]] Authority.
-'''Sulfentrazone''' is a [[Chemical substance|chemical]] used as a  [[herbicide]]. It is the active ingredient in Dismiss as well as Solitare herbicides. It controls [[Weed|weeds]] by disrupting [[Membrane|membranes]] and inhibits [[photosynthesis]] in plants commonly known as PPO Inhibition. Sulfentrazone is received in the plants through the roots of the plants. As the plants come out of the soil , they die after exposure to light. It also works of foliar contact causing rapid desiccation. Sulfentrazone kills annual and perennial [[Cyperaceae|sedges]], cool season grasses(Poa annua, Poa trivialis) The labels on Sulfentrazone product from Ortho indicate use on Well established turf grasses. Cool Season Grasses: [[Agrostis stolonifera|Creeping Bentgrass]], Fine & Tall [[Festuca|Fescue]], [[Lolium perenne|Perennial Ryegrass]], Kentucky & Rough [[Bluegrass (grass)|Bluegrass]]. Warm Season Grasses: [[Paspalum notatum|Bahiagrass]], [[Cynodon dactylon|Bermudagrass]], [[Buffalograss webworm|Buffalograss]], [[Axonopus|Carpetgrass]], [[Eremochloa ophiuroides|Centipedegrass]], [[Pennisetum clandestinum|Kikuyugrass]], [[Paspalum vaginatum|Seashore Paspalum]], [[St. Augustine grass|St. Augustinegrass]], [[Zoysia|Zoysiagrass]].
+== History ==
+In 1985, scientists at FMC Corporation filed patents on a new class of herbicides containing a triazolinone ring.<ref name=US4818275>{{cite patent |country=US |number=4818275|status=patent |gdate=1989-04-04 |fdate=1986-12-31 |pridate=1985-12-20 |invent1 =Theodoridis, George |title=Herbicidal aryl triazolinones |assign1=FMC Corporation |class=A01N43/64  }}</ref> Sulfentrazone was subsequently developed for market under the code number F6285, with first sales in 1991<ref>{{cite book |doi=10.1021/bk-1992-0504.ch014 |chapter=Synthesis and Herbicidal Properties of Aryltriazolinones |title=Synthesis and Chemistry of Agrochemicals III |series=ACS Symposium Series |year=1992 |last1=Theodoridis |first1=George |last2=Baum |first2=Jonathan S. |last3=Hotzman |first3=Frederick W. |last4=Manfredi |first4=Mark C. |last5=Maravetz |first5=Lester L. |last6=Lyga |first6=John W. |last7=Tymonko |first7=John M. |last8=Wilson |first8=Kenneth R. |last9=Poss |first9=Kathleen M. |last10=Wyle |first10=Michael J. |volume=504 |pages=134–146 |isbn=9780841224735 }}</ref> and achieving registration in the US in 1997, branded Authority.<ref>{{ Cite web| url=https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-129081_27-Feb-97.pdf |title=Sulfentrazone Factsheet | work=United States EPA |date=1997-02-27 |access-date=2021-04-19}}</ref> Other compounds now in the triazolinone class include [[amicarbazone]] and [[carfentrazone]].<ref>{{cite web|url=http://www.alanwood.net/pesticides/class_herbicides.html#triazolone_herbicides |title=triazolone herbicides |website=alanwood.net |access-date=2021-04-12}}</ref>
+== 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.<ref name=Dayan /><ref>{{cite book |doi=10.1007/978-3-642-58633-0_11 |chapter=Herbicidal Efficacy of Protoporphyrinogen Oxidase Inhibitors |title=Peroxidizing Herbicides |year=1999 |last1=Nagano |first1=Eiki |pages=296–299 |isbn=978-3-642-63674-5 }}</ref>
+== Usage ==
-Ortho labels state use for removal of sedges and newly emerged broadleaf weeds: purple and yellow [[Cyperus|nutsedge]], ''[[Kyllinga]]'', [[Plantago|plantain]], [[clover]], [[Euphorbia|spurge]], [[Oxalis|woodsorrel]], [[Polygonaceae|knotweed,]] [[Stellaria media|chickweed]], [[Rumex crispus|curly dock]], [[wild onion]], [[wild garlic]], and other listed weeds
+In the [[Pesticide regulation in the United States|United States]], the [[United States Environmental Protection Agency|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.<ref name="epa.gov">{{cite web|url=https://www.epa.gov/pesticide-registration/about-pesticide-registration |title=About Pesticide Registration |publisher=[[Environmental Protection Agency|US EPA]] |access-date=2021-04-19 }}</ref><ref name=USlabel>{{cite web|url=https://www3.epa.gov/pesticides/chem_search/ppls/091234-00009-20151210.pdf |author=US EPA|website=www3.epa.gov|title=Sulfentrazone 4 Herbicide |access-date=2021-04-19}}</ref>
+The label includes use for removal of [[Cyperaceae|sedges]] and newly emerged broadleaf weeds including purple and yellow [[Cyperus|nutsedge]], ''[[Kyllinga]]'', [[Plantago|plantain]], [[clover]], [[Euphorbia|spurge]], [[Oxalis|woodsorrel]], [[Polygonaceae|knotweed,]] [[Stellaria media|chickweed]], [[Rumex crispus|curly dock]], [[wild onion]], and [[wild garlic]]. It is also effective on many grasses including ''[[Poa annua]]'', ''[[Poa trivialis]]'', [[Agrostis stolonifera|creeping bentgrass]], fine & tall [[Festuca|fescue]], [[Lolium perenne|perennial ryegrass]], Kentucky & rough [[Bluegrass (grass)|bluegrass]], [[Paspalum notatum|bahiagrass]], [[Cynodon dactylon|Bermuda grass]], [[Buffalograss webworm|buffalograss]], [[Axonopus|carpetgrass]], [[Eremochloa ophiuroides|centipedegrass]], [[Pennisetum clandestinum|kikuyugrass]], [[Paspalum vaginatum|seashore paspalum]], [[St. Augustine grass]], and [[Zoysia|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.<ref>{{cite journal |last1=Dayan|first1= F.|last2=Weete|first2= J.|last3=Duke|first3=S.|last4= Hancock|first4=H.|date=1997|title= Soybean (Glycine max) cultivar differences in response to sulfentrazone|journal=Weed Science|volume=45|issue=5|pages=634–641|url=https://www.jstor.org/stable/4045886 }}</ref>
+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 {{convert|3800000|lb|kg}} were applied — mainly in soybean.<ref>{{cite web |url=https://water.usgs.gov/nawqa/pnsp/usage/maps/show_map.php?year=2017&map=SULFENTRAZONE&hilo=L&disp=Sulfentrazone |title=Estimated Agricultural Use for Sulfentrazone, 2017  |author=US Geological Survey |access-date=2021-04-19 }}</ref> The compound is not registered for use in the [[European Union]], although another triazolinone, carfentrazone-ethyl, is available there.<ref>{{cite web |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/123.htm |title=Carfentrazone-ethyl |publisher=University of Hertfordshire |author=Pesticide Properties Database |access-date=2021-04-19}}</ref> Sulfentrazone also has uses outside agriculture: it controls vegetation on roadside verges and railroads.<ref>{{cite web |url= https://wsdot.wa.gov/sites/default/files/2008/01/25/Herbicides-factsheet-Sulfentrazone.pdf |title=Sulfentrazone: Roadside Vegetation Management |work=Washington State DOT |date=2017 |access-date=2021-04-19}}</ref><ref>{{cite web |url=https://www3.epa.gov/pesticides/chem_search/ppls/000279-03282-20200417.pdf |title=Sulfentrazone ROW herbicide |work=US EPA label |date=2020-04-17 |access-date=2021-04-19}}</ref> 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.<ref>{{cite web |url=http://npirspublic.ceris.purdue.edu/ppis/default.aspx |author=NPIRS Public |title=Search Federal Pesticide Products }}</ref>
+== Human safety ==
+The [[LD50|LD<sub>50</sub>]] of sulfentrazone is more than 2800&nbsp;mg/kg (rats, oral), which means that it is of low toxicity by oral ingestion.<ref name=PPDB /> The US Code of Federal Regulations records the maximum residue tolerances in various food products.<ref>{{cite web|url=https://ecfr.federalregister.gov/on/2021-04-19/title-40/chapter-I/subchapter-E/part-180/subpart-C/section-180.498|title=Sulfentrazone; tolerances for residues|website=ecfr.federalregister.gov|date=1997-03-10|access-date=2021-04-19}}</ref>
 ==References==
+{{reflist}}
-* {{ Cite web| url=https://www3.epa.gov/pesticides/chem_search/reg_actions/registration/fs_PC-129081_27-Feb-97.pdf|title=Sulfentrazone Factsheet| work=United States EPA}}
-* {{cite web | url=http://www.wsdot.wa.gov/NR/rdonlyres/D703D06E-8038-47D1-A560-AB948C3C8D93/0/Sulfentrazone.pdf|title= Road side use of Sulfentrazone|work=Washington DOT}}
 ==External links==
 * {{PPDB|601}}
 {{Herbicides}}
 [[Category:Herbicides]]
-{{Agriculture-stub}}