Dipropalin

Dipropalin
Names
	Preferred IUPAC name 4-Methyl-2,6-dinitro-N,N-dipropylaniline
	Other names L-35355; 2,6-Dinitro-N,N-dipropyl-p-toluidine; 4-Methyl-2,6-dinitro-N,N-dipropylbenzenamine; 地乐灵 (Geleling);
Identifiers
CAS Number	1918-08-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	15171 ;
PubChem CID	15966;
UNII	389074G62J;
CompTox Dashboard (EPA)	DTXSID1041895 ;
	InChI InChI=1S/C13H19N3O4/c1-4-6-14(7-5-2)13-11(15(17)18)8-10(3)9-12(13)16(19)20/h8-9H,4-7H2,1-3H3 Key: UDVZOMAEGATTSE-UHFFFAOYSA-N;
	SMILES CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C)[N+](=O)[O-];
Properties
Chemical formula	C13H19N3O4
Molar mass	281.312 g·mol−1
Appearance	Yellow crystals
Melting point	42 °C (108 °F; 315 K) [citation needed]
Boiling point	118 °C (244 °F; 391 K)
Solubility in water	0.3 g/L[citation needed]
Hazards
	Lethal dose or concentration (LD, LC):
LC50 (median concentration)	Over 3600 mg/kg (rat, oral)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Dipropalin is a preëmergent dinitroaniline herbicide. It is currenctly not commercially used in western countries,^[1] but may be available in China^[2]^{[unreliable source?]} and used in India.^[3] It has low acute toxicity.^[1] It is used on turf.^[1] Tests in the 1960s in the USA evaluated its performance as a trifluralin analog, where it scored the highest pre-emergent effectiveness amongst methyl-group analogs, though losing to several trifluoromethyls, such as trifluralin itself. Dipropalin's methyl group does see increased post-emergent activity, but no trifluralin analog was effective in this regard.^[4]

References

^ ^a ^b ^c ^d ^e Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (2016-05-18). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment. 22 (4): 1050–1064. Bibcode:2016HERA...22.1050L. doi:10.1080/10807039.2015.1133242. hdl:2299/17565. ISSN 1080-7039.
^ "地乐灵详细信息_百度知道". zhidao.baidu.com.
^ Kukkambakam Chandra Mohan, T. Chandraiah, M. Nagaraju, & N. Y. Sreedhar. (2015). Elucidation of electrochemical reduction behavior of dinitro group containing pesticides Chlornidine, Dipropalin and Prodiamine residues in soil, water and agricultural formulations. Journal of Indian Chemical Society, Vol. 92(Apr 2015), 467–471. https://doi.org/10.5281/zenodo.5595667
^ Gentner, W. A. (1966). "Herbicidal Properties of Trifluralin Analogs". Weeds. 14 (2): 176–178. doi:10.2307/4040959. JSTOR 4040959.

Links

Dipropalin in the Pesticide Properties DataBase (PPDB)

[database-1] Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (2016-05-18). "An international database for pesticide risk assessments and management". Human and Ecological Risk Assessment. 22 (4): 1050–1064. Bibcode:2016HERA...22.1050L. doi:10.1080/10807039.2015.1133242. hdl:2299/17565. ISSN 1080-7039.

[2] "地乐灵详细信息_百度知道". zhidao.baidu.com.

[3] Kukkambakam Chandra Mohan, T. Chandraiah, M. Nagaraju, & N. Y. Sreedhar. (2015). Elucidation of electrochemical reduction behavior of dinitro group containing pesticides Chlornidine, Dipropalin and Prodiamine residues in soil, water and agricultural formulations. Journal of Indian Chemical Society, Vol. 92(Apr 2015), 467–471. https://doi.org/10.5281/zenodo.5595667

[4] Gentner, W. A. (1966). "Herbicidal Properties of Trifluralin Analogs". Weeds. 14 (2): 176–178. doi:10.2307/4040959. JSTOR 4040959.

[1]

[2]

[3]

[4]