Isopropalin
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| Names | |
|---|---|
| Preferred IUPAC name
4-Isopropyl-2,6-dinitro-N,N-dipropylaniline | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.046.977 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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:[3][4] | |
  | |
| 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): | |
LD50 (median dose) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
[edit]Paarlan was a 69% isopropalin emulsifiable concentrate[6] 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.[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).[5]
Safety
[edit]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.[5]
Environmental behaviour
[edit]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.[5]
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.[5]
Chemical properties
[edit]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.[5]
References
[edit]- 1 2 "Isopropalin (Ref: EL-179)". sitem.herts.ac.uk.
- 1 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. Bibcode:1978WeedS..26..527H. doi:10.1017/S0043174500064468. ISSN 0043-1745.
- 1 2 "Label Amendment Submission of 08/30/93 in Response to PR Notice 93-7" (PDF). search.epa.gov. EPA. 1993.
- ↑ "Isopropalin". pubchem.ncbi.nlm.nih.gov.
- 1 2 3 4 5 6 Macbean, C. (2012). A World Compendium The Pesticide Manual (16th ed.). Hampshire, UK: British Crop Protection Council. ISBN 978 1 901396 86 7.
- 1 2 "Paarlan Herbicide Emulsifiable Concentrate" (PDF). search.epa.gov. Elanco. 1975.
- ↑ "Paarlan, An Australia Trademark of DowElanco. Application Number: 255181 :: Trademark Elite Trademarks". www.trademarkelite.com.
- ↑ "Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974". epa.gov. EPA. 1977.
- ↑ Ford, D. H.; Massey, G. D. "Characteristics of the Substituted Dinitroaniline Herbicides, Treflan, Balan, Paarlan, and EL-119".
- ↑ "Paarlan and Tobacco Country USA". NDSU Extension Pesticide Program. 27 January 2023. Retrieved 23 October 2024.
- ↑ "Isopropalin CASRN 33820-53-0 | DTXSID8024157 | IRIS". cfpub.epa.gov. Archived from the original on 7 January 2017.
- ↑ 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.
Links
[edit]- Isopropalin in the Pesticide Properties DataBase (PPDB)