Delachlor

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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[2]
Density 1.101[3]
59 ppm[1]
Hazards
GHS labelling:[2]
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)[2]
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.[1][4] It was first reported in 1967 and introduced by Monsanto,[5] though by 1974 commercial factors had halted its commercialisation,[6] so delachlor is now considered obsolete,[7] and appears never to have been registered in the USA.[8]

Delachlor's HRAC group is Group K (Australia), Group K3 (Global) and Group 15 (numeric).[7]

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.[9]

The LD50 (by mouth) is reported to be 1775 mg/kg on an SDS,[2] but 733 mg/kg on PPDB.[7] The difference is similar to the difference between paracetamol and methanol.

It is soluble in chloroform and somewhat soluble in ethyl acetate.[2]

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