Nitralin

Nitralin[1]
Names
Preferred IUPAC name
4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline
Other names
  • Nitralin
  • Planavin (Brand name)
  • SD 11831 or SD 11 831 (development code)
  • 4-(Methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.022.926 Edit this at Wikidata
EC Number
  • 225-219-0
KEGG
UNII
UN number 3077
  • InChI=1S/C13H19N3O6S/c1-4-6-14(7-5-2)13-11(15(17)18)8-10(23(3,21)22)9-12(13)16(19)20/h8-9H,4-7H2,1-3H3
    Key: UMKANAFDOQQUKE-UHFFFAOYSA-N
  • CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])S(=O)(=O)C)[N+](=O)[O-]
Properties
C13H19N3O6S
Molar mass 345.37 g·mol−1
Appearance Yellow/orange powder[2][3]
Odor Mild odour[3]
Density 1.001[4]
Melting point 151 °C (304 °F; 424 K) [2]
Boiling point 225 °C; 437 °F; 498 K (decomposes)[3]
0.0006 g/L[2]
Solubility in acetone 360 g/L[5]
Solubility in DMSO 330 g/L[5]
Solubility in 2-nitropropane 250 g/L[5]
Vapor pressure 0.2 × 10−6 mm Hg (25°C)[6]
Hazards
GHS labelling:[2][3]
GHS09: Environmental hazard
H228, H410
P273, P391, P501
224 °C; 435 °F; 497 K
Lethal dose or concentration (LD, LC):
>5000 mg/kg[7] (rats and mice); >2000 mg/kg[3] (waterfowl)
46 mg/L (fish)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nitralin is a selective preëmergent dinitroaniline herbicide[8] that is closely related to trifluralin, and released two years later in 1966. Today it is largely obsolete. It was used in the USA, France and Australia to control annual grasses and broad-leaved weeds, and was applied on vines, crops[9][10][11] and turf.[8]

American farmers used 405,000 pounds (184 t) in 1974, though trifluralin still overshadowed it, with 22,960,000 pounds (10,410 t).[12] A 1992 report mentions extensive use on potatoes,[7] though Shell's "Planavin" trademark expired in 1989.[13]

On ryegrass meristems, nitralin suppressed elongation and made the roots wider. After 1 hour, mitosis was reduced by 76%. Cell nuclei expanded, becoming polymorphic, and with increased ploidy levels. Other dinitroanilines have similar effects, except butralin.[14]

Nitralin is not associated with lung cancer.[11]

Planavin

Planavin 75 was sold commercially as a wettable powder containing 75% nitralin, applied at around 2 pounds per acre (2.25 kg/Ha), equivalent to 1.5 lbs/acre of pure nitralin.[8] Shell sold technical grade nitralin at 94% purity for manufacturing purposes.[15]

It is also reported that nitralin is applied at 0.5-0.75 kg/Ha on light soils, and 1-1.5 kg/Ha on heavier soils with over 5% organic mass, while not being used in highly organic or peat soils.[5]

Environmental Behaviour

Soil-applied nitralin is involatile; its vapours were below the limit of detection.[16] Water leaching is very slow. Together this makes nitralin immobile in soil, so application can be precise, though it cannot move far enough into soil to control deep-germinating weed species. Typical in-soil halflives are 30 to 60 days, and it decomposes under ultraviolet light.[17]

Metabolism

Ingested by rats, 98.5% is removed in 72 hours by urine and faeces. The metabolism is complex and produces many afterproducts.[18]

Comparative Performance

Compared to trifluralin, nitralin is more toxic to the roots and less toxic to the shoots. Trifluralin prevented emergence of most species tested; nitralin did not prevent any from emerging.[19] At Johnsongrass control, nitralin and pendimethalin lost out to trifluralin and other dinitroaniline herbicides.[20]

Nitralin in a 1970s trial on conifer seedbeds in Connecticut was effective at 2 lbs/ac (2.24 kg/Ha) though it damaged white spruce seedlings in one test. Of the related dinitroanilines, oryzalin was most active, and nitralin was not far off, beating trifluralin.[21]

Applications

Broadleaves Controlled[8][22][23][18] Grasses Controlled[8][22][23][18] Crops used on Turfs used on[8]
amsinckia, amaranth, buckhorn plantain, bull mallow, carpetweed, common plantain, cress, curly dock (from seed), dead nettle, fat hen, fiddleneck, groundsel, henbit, knotweed, lambsquarter, mallow of Nice, munyeroo, pigweed, plantain, prickly lettuce, price-of-wales feather, purslane, pussley, shepherd's purse, smartweed Annual bluegrass, annual ryegrass, brachiaria, burr grass, cheatgrass, crabgrass, cotton panic grass, cupgrass, downy brome, finger panic grass, goosegrass, green foxtail, ryegrass, johnsongrass, pigeon grass, setaria, watergrass, wild oats, winter grass, wireweed, witchgrass, yellow foxtail vines, soybeans, cotton, beans, groundnuts, sunflowers, tobacco,[9] turf[8] bahia, bentcrass, bermuda grass, annual bluegrass, centipede, fescue, St. Augustine, zoysia, Japanese andromeda, Japanese holly, Azalea, boxwood, chrysanthemum, shasta daisy, ajuga

Nitralin is sparingly soluble in common hydrocarbon or organic solvents.[5]

References

  1. ^ "Nitralin data sheet". www.bcpcpesticidecompendium.org. Compendium of Pesticide Common Names.
  2. ^ a b c d e "Safety data sheet according to 1907/2006/EC, Article 31" (PDF). www.lgcstandards.com. LGC Standards. 9 July 2019. Retrieved 11 October 2024.
  3. ^ a b c d e U.S. Coast Guard (1999). "Chemical Hazards Response Information System (CHRIS) Hazardous Chemical Data; Commandant Instruction 16465.12C" (Technical Report). Washington, DC: Department of Transportation. Retrieved 11 October 2024.
  4. ^ Boyer, Kevin R.; Hodge, Virginia E.; Wetzel, Roger S.; Science Applications International Corporation (September 1987). "Handbook: Responding to Discharges of sinking Hazardous Substances; EPA/540/2-87/001". Environmental Protection Agency.
  5. ^ a b c d e Macbean, C. (2012). A World Compendium The Pesticide Manual (16th ed.). Hampshire, UK: British Crop Protection Council. ISBN 978 1 901396 86 7.
  6. ^ Huffman, J. B.; Camper, N. D. (1978). "Growth Inhibition in Tobacco (Nicotiana tabacum) Callus by 2,6-Dinitroaniline Herbicides and Protection by D-α-Tocopherol Acetate". Weed Science. 26 (6): 527–530. doi:10.1017/S0043174500064468. ISSN 0043-1745. JSTOR 4042920.
  7. ^ a b Thriveni, T.; Rajesh Kumar, J.; Sujatha, D.; Sreedhar, N.Y. (January 2007). "Voltammetric determination of the herbicides nitralin and oryzalin in agricultural formulations, vegetables and grape juice samples". Food Chemistry. 104 (3): 1304–1309. doi:10.1016/j.foodchem.2006.10.014.
  8. ^ a b c d e f g "Planavin 75 Herbicide Wettable Powder" (PDF). Shell Plc. Retrieved 11 October 2024.
  9. ^ a b "Nitralin (Ref: HSDB 789)". Pesticide Properties Database. University of Hertfordshire. Retrieved 10 October 2024.
  10. ^ Elite, Trademark. "PLANAVIN, An Australia Trademark of Shell International Petroleum Co Limited. Application Number: 204428 :: Trademark Elite Trademarks". www.trademarkelite.com.
  11. ^ a b Boulanger, Mathilde; Tual, Séverine; Lemarchand, Clémentine; Baldi, Isabelle; Clin, Bénédicte; Lebailly, Pierre (August 2017). "0441 Exposure to dinitroanilines and risk of lung cancer (Lc) by subtypes: Results from the agrican cohort". Occupational & Environmental Medicine. 74 (Suppl 1): A140.1. doi:10.1136/oemed-2017-104636.365.
  12. ^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
  13. ^ Elite, Trademark. "Trademark Search and Trademark Registration - Register a Trademark and File Your Trademark Application Online". Retrieved 11 October 2024.
  14. ^ Elmore, C. L.; Bayer, D. E. (April 1992). "Mitotic and structural effects of nitralin and butralin on ryegrass ( Lolium perenne L.) root meristems". Weed Research. 32 (2): 77–86. doi:10.1111/j.1365-3180.1992.tb01864.x.
  15. ^ "Pesticide Product Label, TECHNICAL PLANAVIN HERBICIDE FOR MANUFACTURING PURPOSES ONLY" (PDF). www3.epa.gov. Shell Plc. 25 August 1967. Retrieved 11 October 2024.
  16. ^ Ketchersid, M. L.; Bovey, R. W.; Merkle, M. G. (October 1969). "The Detection of Trifluralin Vapors in Air". Weed Science. 17 (4): 484–485. doi:10.1017/S0043174500054631.
  17. ^ "SD 11831 - 'Planavin': An Experimental Herbicide". International Journal of Pest Management: Part C. 13 (3): 253–257. September 1967. doi:10.1080/05331856709432527.
  18. ^ a b c Crayford, J. V.; Hutson, D. H.; Stoydin, G. (January 1984). "The metabolic fate of the herbicide nitralin in the rat". Xenobiotica. 14 (3): 221–233. doi:10.3109/00498258409151407. PMID 6711012.
  19. ^ Barrentine, W. L.; Warren, G. F. (January 1971). "Differential Phytotoxicity of Trifluralin and Nitralin". Weed Science. 19 (1): 31–37. doi:10.1017/S0043174500048219.
  20. ^ Jordan, T. N.; Baker, R. S.; Barrentine, W. L. (1978). "Comparative Toxicity of Several Dinitroaniline Herbicides". Weed Science. 26 (1): 72–75. doi:10.1017/S0043174500032707.
  21. ^ Ahrens, J. F.; Merril, C. G.; Cubanski, M. (September 1976). "Herbicides for Conifer Seedbeds" (PDF). The Connecticut Agricultural Experiment Station (Bulletin 766). New Haven. Retrieved 13 June 2025.
  22. ^ a b "U.S. EPA, Pesticide Product Label, SHELL PLANAVIN 75 HERBICIDE WETTABLE POWDE" (PDF). www3.epa.gov. Shell Plc. Retrieved 11 October 2024.
  23. ^ a b "SHELL PLANAVIN 75 TRADEMARK". myHealthbox. Retrieved 11 October 2024.
  • Nitralin in the Pesticide Properties DataBase (PPDB)

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