Sethoxydim | CAS# 74051-80-2 | Herbicide

MedKoo Cat#: 573654 | Name: Sethoxydim

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Description:

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

Sethoxydim is an herbicide.

Chemical Structure

Sethoxydim

CAS#74051-80-2

Theoretical Analysis

MedKoo Cat#: 573654

Name: Sethoxydim

CAS#: 74051-80-2

Chemical Formula: C17H29NO3S

Exact Mass: 327.1868

Molecular Weight: 327.48

Elemental Analysis: C, 62.35; H, 8.93; N, 4.28; O, 14.66; S, 9.79

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 300.00	2 weeks

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Related CAS #

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Synonym

Aljaden, BAS 9052, BAS 90520H, BAS 9052H, Cyethoxydim, Fervinal, Grasidim, Sethoxydim, Sethoxydime, SN 81742, Tritex-extra

IUPAC/Chemical Name

2-(1-(Ethoxyimino)butyl)-5-(2-ethylthiopropyl)-3-hydroxycyclohex-2-en-1-one

InChi Key

CSPPKDPQLUUTND-NBVRZTHBSA-N

InChi Code

1S/C17H29NO3S/c1-5-8-14(18-21-6-2)17-15(19)10-13(11-16(17)20)9-12(4)22-7-3/h12-13,19H,5-11H2,1-4H3/b18-14+

SMILES Code

C=1(\C(=N\OCC)CCC)C(C[C@@H](C[C@@H](SCC)C)CC1O)=O

Appearance

Solid powder

Purity

>98% (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

To be determined

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

2934.99.9001

More Info

Instruction

View handling instruction

Biological target:

Sethoxydim inhibits plastid acetyl-CoA carboxylase (ACCase) of monocotyledonous species, causing chloroplast bleaching, tissue necrosis, growth reduction, and ultimately death of a plant.

In vitro activity:

This study assessed the antifungal activities of five herbicides against six isolates of Trichoderma species. Sethoxydim had the least deleterious effects Trichoderma sp., while cycloxydim demonstrated significant toxicity. Sethoxydim and cycloxydim exhibited the highest toxicity against Sclerotinia sclerotiorum, with an intermediate level of antifungal activity observed between sethoxydim and haloxyfop ethoxy ethyl. Reference: Pak J Biol Sci. 2007 Jan 1;10(1):7-12. https://pubmed.ncbi.nlm.nih.gov/19069980/

In vivo activity:

When rape leaves were treated with 10(-3) M sethoxydim, growth rate, chlorophyll and lipid contents were reduced, but the plant resisted to herbicide. Lipid synthesis was affected by sethoxydim, probably through inhibition of chloroplast homomeric ACCase activity, and the fatty acid synthase activity (FAS) was reduced because of malonyl-CoA deficiency. Sethoxydim treatment provoked an increase in phenylalanine ammonia lyase (PAL) activity with an accumulation of cinnamic acid, naringenin and anthocyanins. Reference: Pestic Biochem Physiol. 2013 Sep;107(1):120-6. https://pubmed.ncbi.nlm.nih.gov/25149245/

Preparing Stock Solutions

The following data is based on the product molecular weight 327.48 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.

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

Formulation protocol:

1. Pakdaman BS, Goltapeh EM. In vitro studies on the integrated control of rapeseed white stem rot disease through the application of herbicides and Trichoderma species. Pak J Biol Sci. 2007 Jan 1;10(1):7-12. doi: 10.3923/pjbs.2007.7.12. PMID: 19069980. 2. Dotray PA, DiTomaso JM, Gronwald JW, Wyse DL, Kochian LV. Effects of Acetyl-Coenzyme A Carboxylase Inhibitors on Root Cell Transmembrane Electric Potentials in Graminicide-Tolerant and -Susceptible Corn (Zea mays L.). Plant Physiol. 1993 Nov;103(3):919-924. doi: 10.1104/pp.103.3.919. PMID: 12231989; PMCID: PMC159064. 3. Song T, Chu M, Zhang J, Wen R, Lee J, Gossen BD, Yu F, Peng G. Transcriptome analysis identified the mechanism of synergy between sethoxydim herbicide and a mycoherbicide on green foxtail. Sci Rep. 2020 Dec 10;10(1):21690. doi: 10.1038/s41598-020-78290-6. PMID: 33303778; PMCID: PMC7730142. 4. Belkebir A, Benhassaine-Kesri G. Sethoxydim treatment inhibits lipid metabolism and enhances the accumulation of anthocyanins in rape (Brassica napus L.) leaves. Pestic Biochem Physiol. 2013 Sep;107(1):120-6. doi: 10.1016/j.pestbp.2013.06.003. Epub 2013 Jun 20. PMID: 25149245.

In vitro protocol:

In vivo protocol:

1. Song T, Chu M, Zhang J, Wen R, Lee J, Gossen BD, Yu F, Peng G. Transcriptome analysis identified the mechanism of synergy between sethoxydim herbicide and a mycoherbicide on green foxtail. Sci Rep. 2020 Dec 10;10(1):21690. doi: 10.1038/s41598-020-78290-6. PMID: 33303778; PMCID: PMC7730142. 2. Belkebir A, Benhassaine-Kesri G. Sethoxydim treatment inhibits lipid metabolism and enhances the accumulation of anthocyanins in rape (Brassica napus L.) leaves. Pestic Biochem Physiol. 2013 Sep;107(1):120-6. doi: 10.1016/j.pestbp.2013.06.003. Epub 2013 Jun 20. PMID: 25149245.

1: Wang H, Zhang Y, Ren Y, Liu Y, Feng Z, Dong L. Mechanism of multiple resistance to fenoxaprop-P-ethyl, mesosulfuron-methyl, and isoproturon in Avena fatua L. from China. Pestic Biochem Physiol. 2024 Aug;203:105985. doi: 10.1016/j.pestbp.2024.105985. Epub 2024 Jun 16. PMID: 39084789. 2: Li X, Wang L, Li W, Zhang X, Zhang Y, Dong S, Song X, Zhao J, Chen M, Yuan X. Genome-Wide Identification and Expression Profiling of Cytochrome P450 Monooxygenase Superfamily in Foxtail Millet. Int J Mol Sci. 2023 Jul 4;24(13):11053. doi: 10.3390/ijms241311053. PMID: 37446233; PMCID: PMC10341998. 3: Ribeiro VHV, Brunharo CA, Mallory-Smith C, Walenta DL, Barroso J. First report of target-site resistance to ACCase-inhibiting herbicides in Bromus tectorum L. Pest Manag Sci. 2023 Oct;79(10):4025-4033. doi: 10.1002/ps.7607. Epub 2023 Jul 4. PMID: 37309712. 4: Yang Q, Zhu J, Yang X, Wei T, Lv M, Li Y. Ile-1781-Leu Target Mutation and Non-Target-Site Mechanism Confer Resistance to Acetyl-CoA Carboxylase-Inhibiting Herbicides in Digitaria ciliaris var. chrysoblephara. J Agric Food Chem. 2023 May 31;71(21):7988-7995. doi: 10.1021/acs.jafc.3c00646. Epub 2023 May 16. PMID: 37191622. 5: Rigon CAG, Cutti L, Turra GM, Ferreira EZ, Menegaz C, Schaidhauer W, Dayan FE, Gaines TA, Merotto A Jr. Recurrent Selection of Echinochloa crus- galli with a Herbicide Mixture Reduces Progeny Sensitivity. J Agric Food Chem. 2023 May 10;71(18):6871-6881. doi: 10.1021/acs.jafc.3c00920. Epub 2023 Apr 27. PMID: 37104538. 6: Ou Y, Li Y, Feng S, Wang Q, Yang H. Transcriptome Analysis Reveals an Eicosapentaenoic Acid Accumulation Mechanism in a Schizochytrium sp. Mutant. Microbiol Spectr. 2023 Jun 15;11(3):e0013023. doi: 10.1128/spectrum.00130-23. Epub 2023 Apr 24. PMID: 37093006; PMCID: PMC10269799. 7: Mallick B, Rana S, Ghosh TS. Role of herbicides in the decline of butterfly population and diversity. J Exp Zool A Ecol Integr Physiol. 2023 May;339(4):346-356. doi: 10.1002/jez.2688. Epub 2023 Feb 14. PMID: 36789524. 8: Wang J, Peng Y, Chen W, Yu Q, Bai L, Pan L. The Ile-2041-Val mutation in the ACCase gene confers resistance to clodinafop-propargyl in American sloughgrass (Beckmannia syzigachne Steud). Pest Manag Sci. 2021 May;77(5):2425-2432. doi: 10.1002/ps.6271. Epub 2021 Jan 27. PMID: 33432736. 9: Chiellini C, Guglielminetti L, Sarrocco S, Ciurli A. Isolation of Four Microalgal Strains From the Lake Massaciuccoli: Screening of Common Pollutants Tolerance Pattern and Perspectives for Their Use in Biotechnological Applications. Front Plant Sci. 2020 Dec 9;11:607651. doi: 10.3389/fpls.2020.607651. PMID: 33362836; PMCID: PMC7756032. 10: Song T, Chu M, Zhang J, Wen R, Lee J, Gossen BD, Yu F, Peng G. Transcriptome analysis identified the mechanism of synergy between sethoxydim herbicide and a mycoherbicide on green foxtail. Sci Rep. 2020 Dec 10;10(1):21690. doi: 10.1038/s41598-020-78290-6. PMID: 33303778; PMCID: PMC7730142. 11: Nandula VK, Giacomini DA, Lawrence BH, Molin WT, Bond JA. Resistance to clethodim in Italian ryegrass (Lolium perenne ssp. multiflorum) from Mississippi and North Carolina. Pest Manag Sci. 2020 Apr;76(4):1378-1385. doi: 10.1002/ps.5650. Epub 2019 Nov 12. PMID: 31613044. 12: Jouyban A, Farajzadeh MA, Afshar Mogaddam MR. In matrix formation of deep eutectic solvent used in liquid phase extraction coupled with solidification of organic droplets dispersive liquid-liquid microextraction; application in determination of some pesticides in milk samples. Talanta. 2020 Jan 1;206:120169. doi: 10.1016/j.talanta.2019.120169. Epub 2019 Jul 25. PMID: 31514834. 13: Alcántara-de la Cruz R, Domínguez-Martínez PA, da Silveira HM, Cruz-Hipólito HE, Palma-Bautista C, Vázquez-García JG, Domínguez-Valenzuela JA, De Prado R. Management of Glyphosate-Resistant Weeds in Mexican Citrus Groves: Chemical Alternatives and Economic Viability. Plants (Basel). 2019 Sep 4;8(9):325. doi: 10.3390/plants8090325. PMID: 31487903; PMCID: PMC6783860. 14: Liu B, Ding F, Wang M, Wang F, Luo X, Li L. Cross-resistance pattern to ACCase-inhibiting herbicides in a novel Trp1999Leu mutation American sloughgrass (Beckmannia syzigachne) population. Pestic Biochem Physiol. 2019 Sep;159:80-84. doi: 10.1016/j.pestbp.2019.05.019. Epub 2019 May 28. PMID: 31400787. 15: Zhao N, Ge L, Yan Y, Bai S, Wang D, Liu W, Wang J. Trp-1999-Ser mutation of acetyl-CoA carboxylase and cytochrome P450s-involved metabolism confer resistance to fenoxaprop-P-ethyl in Polypogon fugax. Pest Manag Sci. 2019 Dec;75(12):3175-3183. doi: 10.1002/ps.5435. Epub 2019 May 13. PMID: 30950550. 16: Smythers AL, Garmany A, Perry NL, Higginbotham EL, Adkins PE, Kolling DRJ. Characterizing the effect of Poast on Chlorella vulgaris, a non-target organism. Chemosphere. 2019 Mar;219:704-712. doi: 10.1016/j.chemosphere.2018.12.050. Epub 2018 Dec 8. PMID: 30557727. 17: Diao J, Song X, Cui J, Liu L, Shi M, Wang F, Zhang W. Rewiring metabolic network by chemical modulator based laboratory evolution doubles lipid production in Crypthecodinium cohnii. Metab Eng. 2019 Jan;51:88-98. doi: 10.1016/j.ymben.2018.10.004. Epub 2018 Oct 26. PMID: 30393203. 18: Tehranchian P, Nandula V, Jugulam M, Putta K, Jasieniuk M. Multiple resistance to glyphosate, paraquat and ACCase-inhibiting herbicides in Italian ryegrass populations from California: confirmation and mechanisms of resistance. Pest Manag Sci. 2018 Apr;74(4):868-877. doi: 10.1002/ps.4774. Epub 2017 Dec 8. PMID: 29072814. 19: Laforest M, Soufiane B, Simard MJ, Obeid K, Page E, Nurse RE. Acetyl-CoA carboxylase overexpression in herbicide-resistant large crabgrass (Digitaria sanguinalis). Pest Manag Sci. 2017 Nov;73(11):2227-2235. doi: 10.1002/ps.4675. Epub 2017 Sep 11. PMID: 28755464. 20: Liu J, Pei G, Diao J, Chen Z, Liu L, Chen L, Zhang W. Screening and transcriptomic analysis of Crypthecodinium cohnii mutants with high growth and lipid content using the acetyl-CoA carboxylase inhibitor sethoxydim. Appl Microbiol Biotechnol. 2017 Aug;101(15):6179-6191. doi: 10.1007/s00253-017-8397-z. Epub 2017 Jul 3. PMID: 28674851.

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Dibenz[a,h]anthracene