Delachlor

Delachlor
Names
IUPAC name
2-Chloro-2′,6′-dimethyl-N-[(2-methylpropoxy)methyl]acetanilide
Preferred IUPAC name
2-Chloro-N-(2,6-dimethylphenyl)-N-[(2-methylpropoxy)methyl]acetamide
Other names
  • CP 52 223 (development code)
  • 2-Chloro-N-(2,6-dimethylphenyl)-N-[(2-methylpropoxy)methyl]acetamide
  • делахлор (Russian)
  • délachlore (French)
  • 异丁草胺 (Chinese)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C15H22ClNO2/c1-11(2)9-19-10-17(14(18)8-16)15-12(3)6-5-7-13(15)4/h5-7,11H,8-10H2,1-4H3
    Key: BIQOEDQVNIYWPQ-UHFFFAOYSA-N
  • CC1=C(C(=CC=C1)C)N(COCC(C)C)C(=O)CCl
Properties
C15H22ClNO2
Molar mass 283.80 g·mol−1
Appearance colourless or very pale yellow[3]
Density 1.101[4]
59 ppm[1]
Hazards
GHS labelling:[3]
Warning
H302, H312, H315, H317, H319, H332, H351, H361f, H373, H410
P260, P264, P273, P280, P391, P501
Lethal dose or concentration (LD, LC):
  • 1775 mg/kg (mouse, oral)
  • 2000 mg/kg (rat, dermal)[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Delachlor is a chloroacetanilide herbicide, used on grasses, rice and sugarbeet.[1][5] It was first reported in 1967 and introduced by Monsanto,[6] though by 1974 commercial factors had halted its commercialisation,[7] so delachlor is now considered obsolete,[8] and appears never to have been registered in the USA.[9]

Delachlor's HRAC group is Group K (Australia), Group K3 (Global) and Group 15 (numeric).[8]

In artificial soil tests of phytotoxicity, with the herbicides cycloate, benzthiazuron and pyrazon. Delachlor was the most active in organic soils (>11% organics) though cycloate was more potent in other soils.[10]

The LD50 (by mouth) is reported to be 1775 mg/kg on an SDS,[3] but 733 mg/kg on PPDB.[8] The difference is similar to the difference between paracetamol and methanol.

It is soluble in chloroform and somewhat soluble in ethyl acetate.[3]

References

  1. ^ a b c Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V.N.; Gowariker, Sudha (2015). The Pesticide Encyclopedia. CABI. ISBN 978-1-78064-014-3.
  2. ^ "delachlor data sheet". www.bcpcpesticidecompendium.org. Retrieved 22 February 2026.
  3. ^ a b c d e "VEILIGHEIDSINFORMATIEBLAD" [Safety Data Sheet] (PDF). LGC Standards. 12 Feb 2024.
  4. ^ "Delachlor". echemi.com.
  5. ^ Berber, Ahmet Ali; Demi̇R, Şefika Nur; Akinci KenanoğLu, Nihan (25 August 2023). "Potential Health Risks of Chloroacetanilide Herbicides: An In Silico Analysis". Sakarya University Journal of Science. 27 (4): 865–871. doi:10.16984/saufenbilder.1281720.
  6. ^ MacBean, C. (2012). A World Compendium: The Pesticide Manual (Sixteenth ed.). Hampshire: British Crop Production Council. ISBN 978-1-901396-86-7.
  7. ^ BCPC, (1974) "Proceedings 12th British Weed Control Conference", accessed 22nd Feb 2026
  8. ^ a b c Hertfordshire, University of. "Delachlor (Ref: CP 52553), Pesticide Properties Database". sitem.herts.ac.uk.
  9. ^ "Delachlor". ordspub.epa.gov/. EPA Office of Pesticide Programs. Retrieved 16 March 2026.
  10. ^ Horowitz, M.; Blumenfeld, T. (December 1973). "Phytotoxicity of four herbicides in different synthetic soils". Phytoparasitica. 1 (2): 101–110. doi:10.1007/BF02981039.
  • Delachlor in the Pesticide Properties DataBase (PPDB)
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