Isopropalin

Weed control herbicide From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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]

Isopropalin is the most persistent dinitroaniline herbicide in soil, with a field halflife of nearly 10 months, though only 6 months in the greenhouse test. It is one of the least phytotoxic to sorghum, though in weed-control tests had roughly middle of the pack phytotoxicity to weeds.[11]

References

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