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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.878 Edit this at Wikidata
UNII
  • 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 checkY
    Key: SMDHCQAYESWHAE-UHFFFAOYSA-N checkY
  • 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
  • [O-][N+](=O)c1cc(cc([N+]([O-])=O)c1N(CCCC)CC)C(F)(F)F
Properties
C13H16F3N3O4
Molar mass 335.283 g·mol−1
Appearance Orange crystalline solid[1]
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)[1]
Boiling point 121 to 122 °C (250 to 252 °F; 394 to 395 K)[1] at 0.6 mbar
1 mg/L[1]
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).
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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 (320,000 kg) in 2004.[4] Non-agricultural use includes domestic use,[5] turf, golf courses, ornamentals, tree plantations, roads and paths. It is used on lettuce, alfalfa, clover, fruit, nuts, berries, and vineyards.[5] Benfluralin's EU approval expired in 2023,[6] leaving pendimethalin as the only EU-approved dinitroaniline.[7]

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. [5]

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.[5]

After application, benefin must be inforporated into soil. It is usually applied at ~1.2 lb/ac (1.35 kg/Ha) active ingredient.[8]

  1. ^ a b c d 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. ^ a b c d "R.E.D. Facts Benfluralin" (PDF). EPA. July 31, 2004.
  6. ^ "Sowing Resilience: Industry Insights on Europe's Agri-input Challenges and Prospects". Grainews.
  7. ^ 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.
  8. ^ "Balan DF Product Label - 051908 V4D 08G09". www.agrian.com.