Isopropalin

Isopropalin
Names
	Preferred IUPAC name 4-Isopropyl-2,6-dinitro-N,N-dipropylaniline
	Other names Paarlan;
Identifiers
CAS Number	33820-53-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82189 ;
ChEMBL	ChEMBL1256728 ;
ChemSpider	33636 ;
EC Number	251-690-7;
KEGG	C19063 ;
PubChem CID	36606;
UNII	52GZD1I41N;
	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,5-8H2,1-4H3 Key: NEKOXWSIMFDGMA-UHFFFAOYSA-N;
	SMILES CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(C)C)[N+](=O)[O-];
Properties
Chemical formula	C15H23N3O4
Molar mass	309.366 g·mol−1
Appearance	Orange liquid
Solubility in water	0.11ppm
Vapor pressure	30x10-6 mm Hg (30°C)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic to fish
	GHS labelling:
Pictograms
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 [77 °F], 100 kPa). Infobox references

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]

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.^[7] 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."^[8]

Rats fed diets with large amounts of isopropalin had reduced hemoglobin concentrations, lowered hematocrits, and altered organ weights at the higher doses tested.^[9]

References

^ ^a ^b "Isopropalin (Ref: EL-179)". sitem.herts.ac.uk.
^ ^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.
^ ^a ^b "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.
^ ^a ^b "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.
^ 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. Retrieved 23 October 2024.
^ "Isopropalin CASRN 33820-53-0 | DTXSID8024157 | IRIS". cfpub.epa.gov.

Links

Isopropalin in the Pesticide Properties DataBase (PPDB)

[database-1] "Isopropalin (Ref: EL-179)". sitem.herts.ac.uk.

[amogus-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.

[paarlan_1993-3] "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.

[paarlan_1975-5] "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] Ford, D. H.; Massey, G. D. "Characteristics of the Substituted Dinitroaniline Herbicides, Treflan, Balan, Paarlan, and EL-119".

[8] "Paarlan and Tobacco Country USA". NDSU Extension Pesticide Program. Retrieved 23 October 2024.

[9] "Isopropalin CASRN 33820-53-0 | DTXSID8024157 | IRIS". cfpub.epa.gov.

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