Benfluralin

Benfluralin
Names
	Preferred IUPAC name N-Butyl-N-ethyl-2,6-dinitro-4-(trifluoromethyl)aniline
	Other names Benefin; Benfluraline; α,α,α-Trifluoro-2,6-dinitro-N,N-ethylbutyl-p-toluidine
Identifiers
CAS Number	1861-40-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:132878 ;
ChemSpider	2229 ;
ECHA InfoCard	100.015.878
PubChem CID	2319;
UNII	28224BUY6R ;
CompTox Dashboard (EPA)	DTXSID3023899 ;
	InChI InChI=1S/C13H16F3N3O4/c1-3-5-6-17(4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 Key: SMDHCQAYESWHAE-UHFFFAOYSA-N ; InChI=1/C13H16F3N3O4/c1-3-5-6-17(4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 Key: SMDHCQAYESWHAE-UHFFFAOYAK;
	SMILES [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCCC)CC)C(F)(F)F;
Properties
Chemical formula	C13H16F3N3O4
Molar mass	335.283 g·mol−1
Appearance	Orange crystalline solid
Density	1.338 g/mL
Melting point	65.0 to 65.5 °C (149.0 to 149.9 °F; 338.1 to 338.6 K)
Boiling point	121 to 122 °C (250 to 252 °F; 394 to 395 K) at 0.6 mbar
Solubility in water	1 mg/L
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Skin irritation; toxicity to aquatic life
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Benfluralin is an herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development,^[2] same as trifluralin, from which benfluralin was developed in 1963.^[3]

Shows states where benefin (as Balan DF) is registered (Green) or not (Red). Not shown: Hawaii, where it is registered.

It is used to control grasses and other weeds. Annual use in the United States was approximately 700,000 pounds (320 t) in 2004,^[4] down from 1,200,000 pounds (540 t) in 1974, when it was used more than paraquat.^[5] Non-agricultural use includes domestic use,^[6] turf, golf courses, ornamentals, tree plantations, roads and paths. It is used on lettuce, alfalfa, clover, fruit, nuts, berries, and vineyards.^[6] Benfluralin's EU approval expired in 2023,^[7] leaving pendimethalin as the only EU-approved dinitroaniline.^[8]

Benfluralin is practically non-toxic. Chronic exposure may harm the liver and kidneys. No endocrine disruption is known. EPA modelling puts benfluralin water concentrations below any level of concern, and real life evidence shows benfluralin levels to be lower than predicted. ^[6]

Benfluralin's soil half-life is moderate, 22-79 days, and volatilises quickly. It can bioaccumulate in fish, to whom it is very toxic. It is practically non-toxic to birds and bees.^[6]

After application, benefin must be inforporated into soil. It is usually applied at ~1.2 lb/ac (1.35 kg/Ha) active ingredient.^[9]

Lists

Benfluralin has been marketed as: benfluralin, benefin, Bonalan, Carpidor, Benefex, Emblem, Balan, balfin, Surflan XL 2G, XL 2G. (XL 2G tradenames also contain oryzalin.)

Benefin controls the following weeds: (non-exhaustive list) Grasses: Annual bluegrass (Poa annua), barnyardgrass / watergrass (Echinochloa crus-galli), crabgrass Digitaria, crowfootgrass (dactyloctenium aegyptium), foxtails / bottlegrass / bristlegrass / pigeongrass (Setaria), Johnsongrass (seedling only) (Sorghum halepense), junglerice (Echinochloa colonum), fall panicum (panicum dichotomiflorum), Texas panicum / buffalograss / coloradograss (panicum texanum) and ryegrass / sandbur (lolium multiflorum). Weeds: carpetweed (Mollugo verticillata), chickweed (stellaria media), florida pusley / purslane / mexican clover (Richardia scabra), knotweed (Polygonum aviculare), common lambsquarters (Chenopodium album), pigweeds (Amaranthus), common purslane (Portulaca oleracea) and redmaids (Calandrinia ciliata).^[9]

References

^ ^a ^b ^c ^d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
^ Agrochemicals Archived April 6, 2012, at the Wayback Machine, Globachem
^ "Trifluralin - an overview | ScienceDirect Topics". www.sciencedirect.com.
^ R.E.D. FACTS: Benfluralin Archived September 15, 2011, at the Wayback Machine, United States Environmental Protection Agency
^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
^ ^a ^b ^c ^d "R.E.D. Facts Benfluralin" (PDF). EPA. July 31, 2004.
^ "Sowing Resilience: Industry Insights on Europe's Agri-input Challenges and Prospects". Grainews.
^ Giglio, A; Vommaro, ML (November 2022). "Dinitroaniline herbicides: a comprehensive review of toxicity and side effects on animal non-target organisms". Environmental science and pollution research international. 29 (51): 76687–76711. doi:10.1007/s11356-022-23169-4. PMC 9581837. PMID 36175724.
^ ^a ^b "Balan DF Product Label - 051908 V4D 08G09". www.agrian.com.

Links

Benfluralin in the Pesticide Properties DataBase (PPDB)

[GESTIS-1] Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health

[2] Agrochemicals Archived April 6, 2012, at the Wayback Machine, Globachem

[3] "Trifluralin - an overview | ScienceDirect Topics". www.sciencedirect.com.

[4] R.E.D. FACTS: Benfluralin Archived September 15, 2011, at the Wayback Machine, United States Environmental Protection Agency

[5] "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.

[EPA-6] "R.E.D. Facts Benfluralin" (PDF). EPA. July 31, 2004.

[7] "Sowing Resilience: Industry Insights on Europe's Agri-input Challenges and Prospects". Grainews.

[8] Giglio, A; Vommaro, ML (November 2022). "Dinitroaniline herbicides: a comprehensive review of toxicity and side effects on animal non-target organisms". Environmental science and pollution research international. 29 (51): 76687–76711. doi:10.1007/s11356-022-23169-4. PMC 9581837. PMID 36175724.

[label-9] "Balan DF Product Label - 051908 V4D 08G09". www.agrian.com.

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