Nitralin

Last updated
Nitralin [1]
Nitralin.svg
Names
Preferred IUPAC name
4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline
Other names
Nitralin; Planavin; SD 11831; 4-(Methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.022.926 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 225-219-0
KEGG
PubChem CID
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
AppearanceYellow/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 Soluble [2]
Vapor pressure 0.2 x10-6 mm Hg (25°C) [5]
Hazards
GHS labelling: [2] [3]
GHS-pictogram-pollu.svg
H228, H410
P273, P391, P501
224 °C; 435 °F; 497 K
Lethal dose or concentration (LD, LC):
>5000 mg/kg [6] (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 pre-emergent dinitroaniline herbicide [7] 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 [8] [9] [10] and turf. [7]

Contents

American farmers used 405,000 pounds (184 t) in 1974, though trifluralin still overshadowed it, with 22,960,000 pounds (10,410 t). [11] A 1992 report mentions extensive use on potatoes, [6] though Shell's "Planavin" trademark expired in 1989. [12]

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. [13]

Nitralin is not associated with lung cancer. [10]

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. [7] Shell sold technical grade nitralin at 94% purity for manufacturing purposes. [14]

Environmental Behaviour

Soil-applied nitralin is involatile; its vapours were below the limit of detection. [15] 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. [16]

Metabolism

Ingested by rats, 98.5% is removed in 72 hours by urine and faeces. The metabolism is complex and produces many afterproducts. [17]

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. [18] At Johnsongrass control, nitralin and pendimethalin lost out to trifluralin and other dinitroaniline herbicides. [19]

Applications

Broadleaves Controlled [7] [20] [21] [17] Grasses Controlled [7] [20] [21] [17] Crops used onTurfs used on [7]
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, smartweedAnnual 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, [8] turf [7] bahia, bentcrass, bermuda grass, annual bluegrass, centipede, fescue, St. Augustine, zoysia, Japanese andromeda, Japanese holly, Azalea, boxwood, chrysanthemum, shasta daisy, ajuga

Related Research Articles

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<span class="mw-page-title-main">Weed control</span> Botanical component of pest control for plants

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<span class="mw-page-title-main">Glyphosate</span> Systemic herbicide and crop desiccant

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<span class="mw-page-title-main">Paraquat</span> Chemical compound used as an herbicide

Paraquat (trivial name; ), or N,N′-dimethyl-4,4′-bipyridinium dichloride (systematic name), also known as methyl viologen, is a toxic organic compound with the chemical formula [(C6H7N)2]Cl2. It is classified as a viologen, a family of redox-active heterocycles of similar structure. This salt is one of the most widely used herbicides worldwide. It is quick-acting and non-selective, killing green plant tissue on contact.

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<span class="mw-page-title-main">Pendimethalin</span> Chemical compound

Pendimethalin is an herbicide of the dinitroaniline class used premergently and postemergently to control annual grasses and certain broadleaf weeds. It inhibits cell division and cell elongation. Pendimethalin is a K1-group according to the Herbicide Resistance Action Committee (HRAC) classification and is approved in Europe, North America, South America, Africa, Asia and Oceania for different crops including cereals, corn, soybeans, rice, potato, legumes, fruits, vegetables, and nuts, plus lawns and ornamental plants.

<span class="mw-page-title-main">Dicamba</span> Chemical compound used as herbicide

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<span class="mw-page-title-main">Sulfentrazone</span> Chemical compound

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<span class="mw-page-title-main">Trifluralin</span> Weed control herbicide

Trifluralin is a common pre-emergent selective herbicide, a dinitroaniline. With about 14 million pounds (6,400 t) used in the United States in 2001, and 3–7 million pounds (1,400–3,200 t) in 2012, it is one of the most widely used herbicides. Trifluralin is also used in Australia, and New Zealand, previously in the EU. Introduced in 1964, Trifluralin was the first organofluorine compound used as an agrochemical.

<span class="mw-page-title-main">Mesotrione</span> Chemical compound used as an herbicide

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<span class="mw-page-title-main">2,4-Dichlorophenoxyacetic acid</span> Herbicide

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<span class="mw-page-title-main">Benfluralin</span> Chemical compound

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

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<span class="mw-page-title-main">Prosulfocarb</span> Weed control herbicide

Prosulfocarb is a pre-emergent herbicide used agriculturally in Australia, the EU, Japan, New Zealand,, Morocco and Iran, for control of annual ryegrass and toad rush in wheat and barley crops. It was introduced to the EU in 1988 and is rapidly growing in use, with sales increasing by over 500% in France since 2008.

<span class="mw-page-title-main">Profluralin</span> Chemical compound

Profluralin is a dinitroaniline herbicide used preëmergently to control annual grasses and broadleaf weeds, in cotton, soybeans, peanuts, sunflower, cabbage, cauliflower, tomato and others. Profluralin has largely fallen out of use. It rose out of the related, still in common use, trifluralin.

<span class="mw-page-title-main">Butralin</span> Weed control herbicide

Butralin is a herbicide, used to control suckers on tobacco in the United States,, Australia, Mozambique and, for food crops also, China. It is a preëmergent dinitroaniline, first registered in the US in 1976. It was used in the EU, until a ban for exotoxicity in 2009.

<span class="mw-page-title-main">Ethalfluralin</span> Weed control herbicide

Ethalfluralin is a herbicide. It is a preëmergent dinitroaniline developed from trifluralin, used to control annual grasses and broad-leaved weeds. It was synthesised in 1971, first sold in Turkey in 1975, the United States in 1983. It is used on soybeans, peanuts, potatoes, and as of 2023, is the first conventional herbicide the EPA permits on hemp, as ethalfluralin leaves no residue in the plant. Ethalfluralin is not used domestically.

<span class="mw-page-title-main">Isopropalin</span> Weed control herbicide

Isopropalin is a herbicide. Introduced in 1969, it is a preëmergent selective dinitroaniline to control annual grasses and broadleaf weeds. Brought by DowElanco in 1972 to the US and Australia, it is now considered obsolete. In 1974, American farmers used 250,000 pounds (110,000 kg) of isopropalin.

<span class="mw-page-title-main">Chlornidine</span> Weed control herbicide

Chlornidine is a preemergent herbicide. It is a dinitroaniline used in China and India on soybeans, corn, cotton, sorghum, and peanuts.

<span class="mw-page-title-main">Dinitramine</span> Weed control herbicide

Dinitramine is a preëmergent dinitroaniline herbicide incorporated into soil to control weeds for months after. It is no longer approved in the U.S.A., and is not in the European Union, though in Iran it has been used to control annual grasses and broadleaf weeds in cotton and soybeans, as it was in the U.S. as of 1975, where it was also used on sunflower.

References

  1. ↑ "Nitralin data sheet". www.bcpcpesticidecompendium.org. Compendium of Pesticide Common Names.
  2. 1 2 3 4 5 6 "Safety data sheet according to 1907/2006/EC, Article 31" (PDF). www.lgcstandards.com. LGC Standards. 9 July 2019. Retrieved 11 October 2024.
  3. 1 2 3 4 5 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. ↑ 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.
  6. 1 2 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.
  7. 1 2 3 4 5 6 7 "Planavin 75 Herbicide Wettable Powder" (PDF). Shell Plc. Retrieved 11 October 2024.
  8. 1 2 "Nitralin (Ref: HSDB 789)". Pesticide Properties Database. University of Hertfordshire. Retrieved 10 October 2024.
  9. ↑ Elite, Trademark. "PLANAVIN, An Australia Trademark of Shell International Petroleum Co Limited. Application Number: 204428 :: Trademark Elite Trademarks". www.trademarkelite.com.
  10. 1 2 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.
  11. ↑ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
  12. ↑ Elite, Trademark. "Trademark Search and Trademark Registration - Register a Trademark and File Your Trademark Application Online" . Retrieved 11 October 2024.
  13. ↑ 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.
  14. ↑ "Pesticide Product Label, TECHNICAL PLANAVIN HERBICIDE FOR MANUFACTURING PURPOSES ONLY" (PDF). www3.epa.gov. Shell Plc. 25 August 1967. Retrieved 11 October 2024.
  15. ↑ 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.
  16. ↑ "SD 11831 - 'Planavin': An Experimental Herbicide". International Journal of Pest Management: Part C. 13 (3): 253–257. September 1967. doi:10.1080/05331856709432527.
  17. 1 2 3 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.
  18. ↑ Barrentine, W. L.; Warren, G. F. (January 1971). "Differential Phytotoxicity of Trifluralin and Nitralin". Weed Science. 19 (1): 31–37. doi:10.1017/S0043174500048219.
  19. ↑ 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.
  20. 1 2 "U.S. EPA, Pesticide Product Label, SHELL PLANAVIN 75 HERBICIDE WETTABLE POWDE" (PDF). www3.epa.gov. Shell Plc. Retrieved 11 October 2024.
  21. 1 2 "SHELL PLANAVIN 75 TRADEMARK". myHealthbox. Retrieved 11 October 2024.
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