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Butenachlor

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Not to be confused with butachlor.
Butenachlor
Names
Preferred IUPAC name
N-{[(2Z)-But-2-en-1-yloxy]methyl}-2-chloro-N-(2,6-diethylphenyl)acetamide
Other names
  • KH-218, KH 218, KH218
  • N-{[(2Z)-But-2-enyloxy]methyl}-2-chloro-2',6'-diethylacetanilide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C17H24ClNO2/c1-4-7-11-21-13-19(16(20)12-18)17-14(5-2)9-8-10-15(17)6-3/h4,7-10H,5-6,11-13H2,1-3H3/b7-4-
    Key: InChIKey=HZDIJTXDRLNTIS-DAXSKMNVSA-N
  • N(COC/C=C\C)(C(CCl)=O)C1=C(CC)C=CC=C1CC
Properties
C17H24ClNO2
Molar mass 309.83 g·mol−1
Appearance Pale yellow liquid[1]
Density 1.10 kg/L (11 lb/imp. gal)[1]
Melting point 12.9 °C (55.2 °F; 286.0 K)[1]
Boiling point 167 °C (333 °F; 440 K) [1]
29 mg/L[1]
Vapor pressure 0.93 mPa (0.02 mpsf)[1]
Hazards
GHS labelling:[1]
H302, H410
Lethal dose or concentration (LD, LC):
  • >2000 mg/kg (rat)[1]
  • 1630 mg/kg[2]
3.34 mg/L (rat, breathing)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Butenachlor is an obsolete selective chloroacetanilide, chloroacetamide herbicide used to control grasses and broadleaf weeds.[3][4] It was introduced in 1976 and marketed as "Diphenox",[1] by Agro-Kanesho.[5]

Butenachlor's mode of action is to prevent formation of very long chain fatty acids; this makes its HRAC classification Group J (Australia), Group K3 (global) and Group 15 (numeric).[6]

Environmental behaviour

[edit]

Butenachlor does not persist in soil; its soil half-life is 2 to 5 days. It is moderately toxic to fish, with a 96-hour LC50 of 0.48 mg/L (0.034 gr/imp. gal).[1]

References

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  1. ^ a b c d e f g h i j k Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242
  2. ^ "The WHO Guidelines to Classification of Pesticides by Hazard (Extremely Hazardous to Moderately Hazardous)". www.iloencyclopaedia.org. Retrieved 5 February 2026.
  3. ^ "Butenachlor | Product Data Sheet | MedChemExpress". medchemexpress.com. Retrieved 5 February 2026.
  4. ^ Rivard, Linda (2003) "Environmental Fate of Metolachlor", Environmental Monitoring Branch, Department of Pesticide Regulation, Sacramento, California, retrieved 5 Feb 2026
  5. ^ "List of Herbicides Globally". www.weedscience.org.
  6. ^ "Global Herbicide Classification Lookup". Herbicide Resistance Action Committee. Retrieved 5 February 2026.
[edit]
  • Butenachlor in the Pesticide Properties DataBase (PPDB)