Benfluralin

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Benfluralin
File:Benfluralin.svg
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
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UNII
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  • 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]
Vapor pressure 3.7 mPa[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Skin irritation; toxicity to aquatic life
Lethal dose or concentration (LD, LC):
10,000 mg/kg[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benfluralin (or Benefin) is a herbicide of the dinitroaniline class. The mechanism of action of benfluralin involves pre-emergent inhibition of mitosis, root and shoot development,[4] same as trifluralin, from which benfluralin was developed in 1963.[5][6]

File:Registration of benfluralin USA.png
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,[7] down from 1,200,000 pounds (540 t) in 1974, when it was used more than paraquat.[8] The USGS estimates 60,000 pounds (27 t) used in the US in 2018.[9] Non-agricultural use includes domestic use,[10] turf, golf courses, ornamentals, tree plantations, roads and paths. It is used on lettuce, alfalfa, clover, fruit, nuts, berries, and vineyards.[10] Benfluralin's EU approval expired in 2023,[11] leaving pendimethalin as the only EU-approved dinitroaniline.[12]

Benfluralin (as Balan) was registered in Australia from 1967 to 1997, with 200 g/L benfluralin and 680 g/L xylene solvent.[13]

Environmental behaviour

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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.[10]

Vapours of benefin can affect growing tobacco leaves, and exposed leaves are shortened, narrowed, thicker and distorted. Plant height is reduced, though more leaves sprout.[14]

Safety

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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. [10]

Herbicide application

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Benfluralin's HRAC classification is group K1 (global), D (Aus), 3 (numeric).[15]

After application, benefin must be inforporated into soil. It is usually applied at ~1.2 lb/ac (1.35 kg/Ha) active ingredient.[16]

Tradenames

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Benfluralin has been marketed as: Balan, Balfin, Benefex, Benfluralin, Benefin, Bethrodine, Bonalan, Carpidor, Emblem, EL-110, Flubalex, Pel-Tech, Quilan, Surflan XL 2G, Team, and XL 2G. (XL 2G tradenames also contain oryzalin.)[17]

Target weeds

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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).[16]

References

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  1. ^ a b c d Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. ^ (2010). ARS Pesticide Properties Database. U.S. Department of Agriculture. Retrieved from
    https://app.knovel.com/hotlink/toc/id:kpARSPPD03/ars-pesticide-properties/ars-pesticide-properties
  3. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ Agrochemicals Archived April 6, 2012, at the Wayback Machine, Globachem
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  7. ^ R.E.D. FACTS: Benfluralin Archived September 15, 2011, at the Wayback Machine, United States Environmental Protection Agency
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  16. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  17. ^ Greene, Stanley A. Pohanish, Richard P.. (2005). Sittig's Handbook of Pesticides and Agricultural Chemicals. William Andrew Publishing. Retrieved from
    https://app.knovel.com/hotlink/toc/id:kpSHPAC00E/sittigs-handbook-pesticides/sittigs-handbook-pesticides
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  • Benfluralin in the Pesticide Properties DataBase (PPDB)
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