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
Density 1.101
59 ppm
Hazards
GHS labelling:
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

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

Effectiveness

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.

Delachlor appears to be used in China, where it has reportedly good control of goosegrass.

Safety

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

Chemistry

It is soluble in chloroform and somewhat soluble in ethyl acetate.

References

  1. 1 2 3 Paranjape, Kalyani; Gowariker, Vasant; Krishnamurthy, V.N.; Gowariker, Sudha (2015). The Pesticide Encyclopedia. CABI. ISBN 978-1-78064-014-3.
  2. 1 2 3 4 5 "VEILIGHEIDSINFORMATIEBLAD" [Safety Data Sheet] (PDF). LGC Standards. 12 February 2024.
  3. ↑ "Delachlor". echemi.com.
  4. ↑ 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. hdl:20.500.12428/14868.
  5. ↑ MacBean, C. (2012). A World Compendium: The Pesticide Manual (Sixteenth ed.). Hampshire: British Crop Production Council. ISBN 978-1-901396-86-7.
  6. ↑ BCPC, (1974) "Proceedings 12th British Weed Control Conference", accessed 22nd Feb 2026
  7. 1 2 3 Hertfordshire, University of. "Delachlor (Ref: CP 52553), Pesticide Properties Database". sitem.herts.ac.uk.
  8. ↑ "Delachlor". ordspub.epa.gov/. EPA Office of Pesticide Programs. Retrieved 16 March 2026.
  9. ↑ Horowitz, M.; Blumenfeld, T. (December 1973). "Phytotoxicity of four herbicides in different synthetic soils". Phytoparasitica. 1 (2): 101–110. doi:10.1007/BF02981039.
  10. ↑ "Cleavers". www.herbiguide.com.au.