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Dipropalin

Not to be confused with Dipropylin.

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
3D model (JSmol)
ChemSpider
UNII
  • 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
  • CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C)[N+](=O)[O-]
Properties
C13H19N3O4
Molar mass 281.312 g·mol−1
Appearance Yellow crystals[1]
Melting point 42 °C (108 °F; 315 K) [citation needed]
Boiling point 118 °C (244 °F; 391 K)
0.3 g/L[citation needed]
Hazards
Lethal dose or concentration (LD, LC):
Over 3600 mg/kg (rat, oral)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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] Dipropalin is chemically identical to trifluralin, except that trifluralin's trifluoromethyl group is switched for dipropalin's methyl.[5]

In another study, dipropalin scored better than trifluralin at controlling broadleaf weeds, but worse at grassy weeds, and much worse against sedges. Neither herbicide caused crop injury, even at 20 lb/ac. active ingredient applied,[6] and another study found dipropalin to be much less effective against bluegrass than trifluralin, and with 80% control of crabgrass, though many tested herbicides achieved better, including trifluralin at 98%.[5]

References

  1. ^ a b c d e Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (18 May 2016). "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.
  5. ^ a b Singh, R. K. N.; Campbell, R. W. (1965). "Herbicides on Bluegrass". Weeds. 13 (2): 170–171. doi:10.2307/4041163. ISSN 0096-719X. Retrieved 14 February 2026.
  6. ^ Taylor, J. L. (1962). "PREEMERGENCE WEED CONTROL IN FIELD GROWN WOODY ORNAMENTAL PLANTS". Florida State Horticultural Society. Gainesville: University of Florida.
  • Dipropalin in the Pesticide Properties DataBase (PPDB)

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