clethodim (CHEBI:70721)

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ChEBI Name	clethodim

ChEBI ID	CHEBI:70721

Definition	An oxime O-ether resulting from the formal conversion ot the acyclic keto group of 5-[2-(ethylsulfanyl)propyl]-3-hydroxy-2-propionylcyclohex-2-en-1-one to the corresponding oxime with subsequent O-alkylation of the oxime by an (E)-3-chloroallyl group. It is used as a selective postemergence herbicide for the control of annual and perennial grasses in numerous crops, including alfalfa, celery, clover, conifers, cotton, cranberries, garlic, onions, ornamentals, peanuts, soybeans, strawberries, sugarbeet, sunflowers, and vegetables; the (−)-enantiomer has been reported to be more active than the (+)-enantiomer.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information	ChemicalBook:CB5855401, ZINC000005854633

Download	Molfile XML SDF

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Formula

C17H26ClNO3S

Net Charge

Average Mass

359.91100

Monoisotopic Mass

359.13219

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?

InChIKey

SILSDTWXNBZOGF-JWGBMQLESA-N

SMILES

CCSC(C)CC1CC(=O)C(=C(O)C1)C(CC)=NOC\C=C\Cl

Roles Classification
Biological Role(s):	EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor An EC 6.4.1.* (C1C bond-forming ligase) inhibitor that interferes with the action of acetyl-CoA carboxylase (EC 6.4.1.2).

Application(s):	herbicide A substance used to destroy plant pests.

ChEBI Ontology
Outgoing	clethodim (CHEBI:70721) has role EC 6.4.1.2 (acetyl-CoA carboxylase) inhibitor (CHEBI:70722) clethodim (CHEBI:70721) has role herbicide (CHEBI:24527) clethodim (CHEBI:70721) is a β-diketone (CHEBI:67265) clethodim (CHEBI:70721) is a cyclic ketone (CHEBI:3992) clethodim (CHEBI:70721) is a enol (CHEBI:33823) clethodim (CHEBI:70721) is a organic sulfide (CHEBI:16385) clethodim (CHEBI:70721) is a organochlorine compound (CHEBI:36683) clethodim (CHEBI:70721) is a oxime O-ether (CHEBI:36816)

IUPAC Name

2-(N-{[(2E)-3-chloroprop-2-en-1-yl]oxy}propanimidoyl)-5-[2-(ethylsulfanyl)propyl]-3-hydroxycyclohex-2-en-1-one

Synonym	Source
2-[1-[[[(2E)-3-chloro-2-propen-1-yl]oxy]imino]propyl]-5-[2-(ethylthio)propyl]-3-hydroxy-2-cyclohexen-1-one	ChEBI

Last Modified

04 August 2014

General Comments
2012-10-20	Note from Barrie Walker (19/10/2012): The material has E stereochem at the allyl double bond, but undefined stereo (geometry) at the oxime double bond. The CAS number remains the same (I persuaded CAS to retain it). This was a revision to the original definition which took place about 3 years ago. There are several possible tautomers but all have the undefined oxime double bond.
2012-10-20	The name clethodim was originally approved for the substance with (E)-stereochemistry at the C=N double bond, but in 2008 the manufacturer determined that the (Z)-isomer is also present in the manufactured product and requested that the definition be changed.