PROFILPELAJAR.COM

Isopropalin

Isopropalin
Names
Preferred IUPAC name
4-Isopropyl-2,6-dinitro-N,N-dipropylaniline
Other names
  • Paarlan
  • EL-179 (development code)
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 30 × 10−6 mm Hg (30°C)[2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic to fish
GHS labelling:[4][5]
GHS05: CorrosiveGHS09: Environmental hazard
Warning
H226, H410
P210, P233, P240, P241, P242, P243, P273, P280, P303+P361+P353, P370+P378, P391, P403+P235, P501
Lethal dose or concentration (LD, LC):
  • >5000mg/kg (oral, rats)
  • >2000mg/kg (dog/rabbit)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isopropalin is a herbicide. Invented 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][6][7] In 1974, American farmers used 250,000 pounds (110,000 kg) of isopropalin.[8]

Paarlan

Paarlan was a 69% isopropalin emulsifiable concentrate[6] approved for use on tobacco.[4] 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.[9] 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."[10]

Paarlan was applied at 1-2 kg/Ha (active ingredient).[3]

Safety

Rats fed diets with large amounts of isopropalin had reduced hemoglobin concentrations, lowered hematocrits, and altered organ weights at the higher doses tested.[11] It is slightly irritating to skin and eyes. Its NOEL on dogs is over 250 mg/kg dietary.[3]

Environmental behaviour

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.[12]

Isopropalin is not toxic to chickens, mallard ducks, (LD50 >2000 mg/kg) or quail (>1000 mg/kg). The LC50 for goldfish is >0.15 mg/L, for minnows, >0.1 mg/L.[3]

It does not translocate, in plants, to the leaves or fruit, and no significatn residues or metabolites have been detected. Isopropalin is strongly absorbed in soil, with minimal leaching, and a soil half-life of under 6 months. The loss in soil is possibly from microörgamisms, volatilisation and photolysis of ispropalin on the surface.[3]

Chemical properties

Isopropalin is only one part in a million soluble in water, but dissolves readily, to more than 1000 g/L, in acetone, hexane, benzene, chloroform, diethyl ether, acetonitrile and methanol. It is stable in field use, but decomposes in laboratory under UV light.[3]

References

  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. Bibcode:1978WeedS..26..527H. doi:10.1017/S0043174500064468. ISSN 0043-1745.
  3. ^ a b c d e f Macbean, C. (2012). A World Compendium The Pesticide Manual (16th ed.). Hampshire, UK: British Crop Protection Council. ISBN 978 1 901396 86 7.
  4. ^ a b "Label Amendment Submission of 08/30/93 in Response to PR Notice 93-7" (PDF). search.epa.gov. EPA. 1993.
  5. ^ "Isopropalin". pubchem.ncbi.nlm.nih.gov.
  6. ^ a b "Paarlan Herbicide Emulsifiable Concentrate" (PDF). search.epa.gov. Elanco. 1975.
  7. ^ "Paarlan, An Australia Trademark of DowElanco. Application Number: 255181 :: Trademark Elite Trademarks". www.trademarkelite.com.
  8. ^ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
  9. ^ Ford, D. H.; Massey, G. D. "Characteristics of the Substituted Dinitroaniline Herbicides, Treflan, Balan, Paarlan, and EL-119".
  10. ^ "Paarlan and Tobacco Country USA". NDSU Extension Pesticide Program. 27 January 2023. Retrieved 23 October 2024.
  11. ^ "Isopropalin CASRN 33820-53-0 | DTXSID8024157 | IRIS". cfpub.epa.gov. Archived from the original on 7 January 2017.
  12. ^ Stoller, E. W.; Wax, L. M. (1977). "Persistence and Activity of Dinitroaniline Herbicides in Soil". Journal of Environmental Quality. 6 (2): 124–127. Bibcode:1977JEnvQ...6..124S. doi:10.2134/jeq1977.00472425000600020004x.
  • Isopropalin in the Pesticide Properties DataBase (PPDB)

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.