Clethodim

Clethodim
	source ↗
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
CAS Number	99129-21-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70721;
ChEMBL	ChEMBL111058;
ChemSpider	11677232;
ECHA InfoCard	100.128.422
EC Number	619-396-7;
KEGG	C18609;
PubChem CID	135491728;
UNII	05SB62IB6F;
CompTox Dashboard (EPA)	DTXSID3034458 ;
	InChI 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;
	SMILES CC/C(=N\OC/C=C/Cl)/C1=C(CC(CC1=O)CC(C)SCC)O;
Properties
Chemical formula	C17H26ClNO3S
Molar mass	359.91 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H317, H412
Precautionary statements	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). Infobox references

Clethodim is an herbicide of the cyclohexanedione family. It is used to control grasses, especially annual ryegrass (Lolium rigidum).¹² 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

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.
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.
"Classification of Herbicides According to Site of Action". Retrieved 19 July 2025.

[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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