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MedKoo Cat#: 461188 | Name: Clethodim
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clethodim is a acetyl-coenzyme A carboxylase (ACCase)-inhibiting cyclohexanedione herbicide used to control grass weeds infesting dicot crops.

Chemical Structure

Clethodim
Clethodim
CAS#99129-21-2

Theoretical Analysis

MedKoo Cat#: 461188

Name: Clethodim

CAS#: 99129-21-2

Chemical Formula: C17H26ClNO3S

Exact Mass: 359.1322

Molecular Weight: 359.90

Elemental Analysis: C, 56.73; H, 7.28; Cl, 9.85; N, 3.89; O, 13.34; S, 8.91

Price and Availability

Size Price Availability Quantity
50mg USD 450.00 2 Weeks
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Related CAS #
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Synonym
Clethodim; Centurion; Prism; RE 45601; RE-45601; RE45601; Trigger;
IUPAC/Chemical Name
(S)-2-((E)-1-((((Z)-3-chloroallyl)oxy)imino)propyl)-5-((R)-2-(ethylthio)propyl)-3-hydroxycyclohex-2-en-1-one
InChi Key
SILSDTWXNBZOGF-LQRZKSEJSA-N
InChi Code
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+/t12-,13+/m1/s1
SMILES Code
O=C1C[C@H](CC(O)=C1/C(CC)=N/OC/C=C\Cl)C[C@H](SCC)C
Appearance
Solid powder
Purity
>94% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 359.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: You X, Liang L, Liu F. Dissipation and residues of clethodim and its oxidation metabolites in a rape-field ecosystem using QuEChERS and liquid chromatography/tandem mass spectrometry. Food Chem. 2014 Jan 15;143:170-4. doi: 10.1016/j.foodchem.2013.07.090. Epub 2013 Jul 26. PubMed PMID: 24054227. 2: Sevilla-Morán B, Alonso-Prados JL, García-Baudín JM, Sandín-España P. Indirect photodegradation of clethodim in aqueous media. byproduct identification by quadrupole time-of-flight mass spectrometry. J Agric Food Chem. 2010 Mar 10;58(5):3068-76. doi: 10.1021/jf9034173. PubMed PMID: 20128587. 3: Yu Q, Collavo A, Zheng MQ, Owen M, Sattin M, Powles SB. Diversity of acetyl-coenzyme A carboxylase mutations in resistant Lolium populations: evaluation using clethodim. Plant Physiol. 2007 Oct;145(2):547-58. Epub 2007 Aug 24. PubMed PMID: 17720757; PubMed Central PMCID: PMC2048730. 4: Webster TM, Hanna WW, Mullinix BG Jr. Bermudagrass (Cynodon spp) dose-response relationships with clethodim, glufosinate and glyphosate. Pest Manag Sci. 2004 Dec;60(12):1237-44. PubMed PMID: 15578605. 5: Ishimitsu S, Kaihara A, Yoshii K, Tsumura Y, Nakamura Y, Tonogai Y. Determination of clethodim and its oxidation metabolites in crops by liquid chromatography with confirmation by LC/MS. J AOAC Int. 2001 Jul-Aug;84(4):1172-8. PubMed PMID: 11501920. 6: Guo W, Yuan G, Liu W, Bi Y, Du L, Zhang C, Li Q, Wang J. Multiple resistance to ACCase and AHAS-inhibiting herbicides in shortawn foxtail (Alopecurus aequalis Sobol.) from China. Pestic Biochem Physiol. 2015 Oct;124:66-72. doi: 10.1016/j.pestbp.2015.04.006. Epub 2015 May 8. PubMed PMID: 26453232. 7: Yuan G, Liu W, Bi Y, Du L, Guo W, Wang J. Molecular basis for resistance to ACCase-inhibiting herbicides in Pseudosclerochloa kengiana populations. Pestic Biochem Physiol. 2015 Mar;119:9-15. doi: 10.1016/j.pestbp.2015.03.004. Epub 2015 Mar 11. PubMed PMID: 25868811. 8: Marek LJ, Koskinen WC, Bresnahan GA. LC/MS analysis of cyclohexanedione oxime herbicides in water. J Agric Food Chem. 2000 Jul;48(7):2797-801. PubMed PMID: 10898624. 9: Li L, Du L, Liu W, Yuan G, Wang J. Target-site mechanism of ACCase-inhibitors resistance in American sloughgrass (Beckmannia syzigachne Steud.) from China. Pestic Biochem Physiol. 2014 Mar;110:57-62. doi: 10.1016/j.pestbp.2014.03.001. Epub 2014 Mar 14. PubMed PMID: 24759052. 10: Du L, Liu W, Yuan G, Guo W, Li Q, Wang J. Cross-resistance patterns to ACCase-inhibitors in American sloughgrass (Beckmannia syzigachne Steud.) homozygous for specific ACCase mutations. Pestic Biochem Physiol. 2016 Jan;126:42-8. doi: 10.1016/j.pestbp.2015.07.005. Epub 2015 Aug 3. PubMed PMID: 26778433. 11: Wang F, Yang G, Xu J, Yu W, Shi L, Zeng S, Chen L, Hu D, Zhang K. Simultaneous determination and method validation of clethodim and its metabolites clethodim sulfoxide and clethodim sulfone in tobacco by LC-MS/MS. Biomed Chromatogr. 2018 Apr;32(4). doi: 10.1002/bmc.4148. Epub 2017 Dec 8. PubMed PMID: 29165829. 12: Tehranchian P, Norsworthy JK, Korres NE, McElroy S, Chen S, Scott RC. Resistance to aryloxyphenoxypropionate herbicides in Amazon sprangletop: Confirmation, control, and molecular basis of resistance. Pestic Biochem Physiol. 2016 Oct;133:79-84. doi: 10.1016/j.pestbp.2016.02.010. Epub 2016 Mar 2. PubMed PMID: 27742365. 13: Fan T, Wu X, Peng Q. Sparingly soluble pesticide dissolved in ionic liquid aqueous. J Phys Chem B. 2014 Oct 2;118(39):11546-51. doi: 10.1021/jp505376w. Epub 2014 Sep 22. PubMed PMID: 25222470. 14: Kaundun SS, Hutchings SJ, Dale RP, McIndoe E. Broad resistance to ACCase inhibiting herbicides in a ryegrass population is due only to a cysteine to arginine mutation in the target enzyme. PLoS One. 2012;7(6):e39759. doi: 10.1371/journal.pone.0039759. Epub 2012 Jun 29. PubMed PMID: 22768118; PubMed Central PMCID: PMC3387263. 15: Incledon BJ, Hall JC. Inhibition of ACCase220 and ACCase240 isozymes from sethoxydim-resistant and -susceptible maize hybrids. J Agric Food Chem. 1999 Jan;47(1):299-304. PubMed PMID: 10563889. 16: Villaverde JJ, Sevilla-Morán B, López-Goti C, Calvo L, Alonso-Prados JL, Sandín-España P. Photolysis of clethodim herbicide and a formulation in aquatic environments: Fate and ecotoxicity assessment of photoproducts by QSAR models. Sci Total Environ. 2018 Feb 15;615:643-651. doi: 10.1016/j.scitotenv.2017.09.300. Epub 2017 Oct 17. PubMed PMID: 28992491. 17: Liu J, Tong L, Meng W, Zhao Y, Yu Z. [Determination of 135 pesticides and their metabolites in Angelica sinensis by ultra-fast liquid chromatography-tandem mass spectrometry coupled with solid-phase extraction]. Se Pu. 2015 Dec;33(12):1257-68. Chinese. PubMed PMID: 27097459. 18: Saini RK, Malone J, Gill G, Preston C. Inheritance of evolved clethodim resistance in Lolium rigidum populations from Australia. Pest Manag Sci. 2017 Aug;73(8):1604-1610. doi: 10.1002/ps.4493. Epub 2017 Jan 4. PubMed PMID: 27933726. 19: Fan T, Chen C, Fan T, Liu F, Peng Q. Novel surface-active ionic liquids used as solubilizers for water-insoluble pesticides. J Hazard Mater. 2015 Oct 30;297:340-6. doi: 10.1016/j.jhazmat.2015.05.034. Epub 2015 May 20. PubMed PMID: 26047302. 20: Délye C, Matéjicek A, Michel S. Cross-resistance patterns to ACCase-inhibiting herbicides conferred by mutant ACCase isoforms in Alopecurus myosuroides Huds. (black-grass), re-examined at the recommended herbicide field rate. Pest Manag Sci. 2008 Nov;64(11):1179-86. doi: 10.1002/ps.1614. PubMed PMID: 18537107.