Clethodim

Clethodim
Names
IUPAC name
2-[(E)-N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-5-(2-ethylsulfanylpropyl)-3-hydroxycyclohex-2-en-1-one
Other names
Centurion, Centurion Plus, Chevron RE 45601, cletodime
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.128.422 Edit this at Wikidata
EC Number
  • 619-396-7
KEGG
UNII
  • InChI=1S/C17H26ClNO3S/c1-4-14(19-22-8-6-7-18)17-15(20)10-13(11-16(17)21)9-12(3)23-5-2/h6-7,12-13,20H,4-5,8-11H2,1-3H3/b7-6+,19-14+
    Key: SILSDTWXNBZOGF-KUZBFYBWSA-N
  • CC/C(=N\OC/C=C/Cl)/C1=C(CC(CC1=O)CC(C)SCC)O
Properties
C17H26ClNO3S
Molar mass 359.91 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H317, H412
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Clethodim (or cletodime) is an herbicide of the cyclohexanedione family. It is used to control grasses, especially annual ryegrass (Lolium rigidum). Although impure samples appear yellowish, the compound is colorless.

Clethodim's HRAC classification is Group A (Australia and global) or Group 1 (numeric). Group A herbicides inhibit acetyl-CoA carboxylase (ACCase).

References

  1. ↑ Watson, Keith G. (2011). "Cyclohexane-1,3-dione Oxime Ether Grass-Specific Herbicides and the Discovery of Butroxydim". Australian Journal of Chemistry. 64 (4): 367. doi:10.1071/CH10366.
  2. ↑ Yu, Qin; Collavo, Alberto; Zheng, Ming-Qi; Owen, Mechelle; Sattin, Maurizio; Powles, Stephen B. (2007). "Diversity of Acetyl-Coenzyme a Carboxylase Mutations in Resistant Lolium Populations: Evaluation Using Clethodim". Plant Physiology. 145 (2): 547–558. doi:10.1104/pp.107.105262. PMC 2048730. PMID 17720757.
  3. ↑ "Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.