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Isopropalin

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Weed control herbicide
Isopropalin
Names
Preferred IUPAC name 4-Isopropyl-2,6-dinitro-N,N-dipropylaniline
Other names
  • Paarlan
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.977 Edit this at Wikidata
EC Number
  • 251-690-7
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H23N3O4/c1-5-7-16(8-6-2)15-13(17(19)20)9-12(11(3)4)10-14(15)18(21)22/h9-11H,5-8H2,1-4H3Key: NEKOXWSIMFDGMA-UHFFFAOYSA-N
SMILES
  • CCCN(CCC)C1=C(C=C(C=C1(=O))C(C)C)(=O)
Properties
Chemical formula C15H23N3O4
Molar mass 309.366 g·mol
Appearance Orange liquid
Solubility in water 0.11ppm
Vapor pressure 30x10 mm Hg (30°C)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Toxic to fish
GHS labelling:
Pictograms GHS05: CorrosiveGHS09: Environmental hazard
Signal word Warning
Hazard statements H226, H410
Precautionary statements P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P391, P403+P235, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Paarlan was a 69% isopropalin emulsifiable concentrate approved for use on tobacco. It required soil incorporation due to low solubility, ultraviolet light degradation and high volatilisation, and it may have been registered for white potatoes and tomatoes. Dow marketed Paarlan to southern culture, with a video advert claiming it "is just as much a part of tobacco country as ham and biscuits are part of breakfast."

Rats fed diets with large amounts of isopropalin had reduced hemoglobin concentrations, lowered hematocrits, and altered organ weights at the higher doses tested.

References

  1. ^ "Isopropalin (Ref: EL-179)". sitem.herts.ac.uk.
  2. ^ 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. ISSN 0043-1745.
  3. ^ "Label Amendment Submission of 08/30/93 in Response to PR Notice 93-7" (PDF). search.epa.gov. EPA. 1993.
  4. "Isopropalin". pubchem.ncbi.nlm.nih.gov.
  5. ^ "Paarlan Herbicide Emulsifiable Concentrate" (PDF). search.epa.gov. Elanco. 1975.
  6. "Paarlan, An Australia Trademark of DowElanco. Application Number: 255181 :: Trademark Elite Trademarks". www.trademarkelite.com.
  7. "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
  8. Ford, D. H.; Massey, G. D. "Characteristics of the Substituted Dinitroaniline Herbicides, Treflan, Balan, Paarlan, and EL-119".
  9. "Paarlan and Tobacco Country USA". NDSU Extension Pesticide Program. Retrieved 23 October 2024.
  10. "Isopropalin CASRN 33820-53-0 | DTXSID8024157 | IRIS". cfpub.epa.gov.

Links

  • Isopropalin in the Pesticide Properties DataBase (PPDB)
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