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Isopropalin

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Isopropalin
Names
Preferred IUPAC name
4-Isopropyl-2,6-dinitro-N,N-dipropylaniline
Other names
  • Paarlan
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.046.977 Edit this at Wikidata
EC Number
  • 251-690-7
KEGG
UNII
  • 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,5-8H2,1-4H3
    Key: NEKOXWSIMFDGMA-UHFFFAOYSA-N
  • CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(C)C)[N+](=O)[O-]
Properties
C15H23N3O4
Molar mass 309.366 g·mol−1
Appearance Orange liquid[1]
0.11ppm[2]
Vapor pressure 30x10-6 mm Hg (30°C)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic to fish
GHS labelling:[3][4]
GHS05: CorrosiveGHS09: Environmental hazard
Warning
H226, H410
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 [77 °F], 100 kPa).

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.[1][5][6] In 1974, American farmers used 250,000 pounds (110,000 kg) of isopropalin.[7]

Paarlan was a 69% isopropalin emulsifiable concentrate[5] approved for use on tobacco.[3] 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.[8] 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."[9]

Rats fed diets with large amounts of isopropalin had reduced hemoglobin concentrations, lowered hematocrits, and altered organ weights at the higher doses tested.[10]

References

[edit]
  1. ^ a b "Isopropalin (Ref: EL-179)". sitem.herts.ac.uk.
  2. ^ a b 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. ^ a b "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. ^ a b "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.
[edit]
  • Isopropalin in the Pesticide Properties DataBase (PPDB)
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