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
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 is an herbicide of the cyclohexanedione family. It is used to control grasses, especially annual ryegrass (Lolium rigidum).[1][2] 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).[3]

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.

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