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MedKoo Cat#: 329865 | Name: Clomazone
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Description:

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

Clomazone, also known as Dimethazone, is an agricultural herbicide, and has been the active ingredient of products named "Command" and "Commence". The molecule consists of a 2-chlorobenzyl group bound to a N-O heterocycle called Isoxazole. Clomazone suppresses the biosynthesis of chlorophyll and other plant pigments.

Chemical Structure

Clomazone
Clomazone
CAS#81777-89-1

Theoretical Analysis

MedKoo Cat#: 329865

Name: Clomazone

CAS#: 81777-89-1

Chemical Formula: C12H14ClNO2

Exact Mass: 239.0713

Molecular Weight: 239.70

Elemental Analysis: C, 60.13; H, 5.89; Cl, 14.79; N, 5.84; O, 13.35

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
250mg USD 650.00 2 Weeks
1g USD 1,450.00 2 Weeks
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Related CAS #
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Synonym
Clomazone; Dimethazone; FMC 57020; FMC57020; FMC-57020; Gamit; Magister; Command.
IUPAC/Chemical Name
2-(2-Chlorobenzyl)-4,4-dimethylisoxazolidin-3-one
InChi Key
KIEDNEWSYUYDSN-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H14ClNO2/c1-12(2)8-16-14(11(12)15)7-9-5-3-4-6-10(9)13/h3-6H,7-8H2,1-2H3
SMILES Code
O=C1N(CC2=CC=CC=C2Cl)OCC1(C)C
Appearance
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
Soluble in DMSO
Shelf Life
>2 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
Clomazone is used for broadleaf weed control in several crops, including soybeans, peas, maize, oilseed rape, sugar cane, cassava, pumpkins and tobacco. It may be applied pre-emergence of incorporated before planting the crop. Clomazone is relatively volatile (vapor pressure is 19.2 mPa) and vapors induce striking visual symptoms on non-target sensitive plants. Clomazone undergoes biological degradation, exhibiting a soil half life of one to four months. Adsorption of the herbicide to soil solids slows degradation and volatilization. Encapsulation helps reduce volatility and therefore reduces off-target damage to sensitive plants. (https://en.wikipedia.org/wiki/Clomazone)

Preparing Stock Solutions

The following data is based on the product molecular weight 239.70 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: Van Scoy AR, Tjeerdema RS. Environmental fate and toxicology of clomazone. Rev Environ Contam Toxicol. 2014;229:35-49. doi: 10.1007/978-3-319-03777-6_3. Review. PubMed PMID: 24515809. 2: Cao J, Li P, Li QX, Zheng P, Diao X. Bioaccumulation and Elimination of the Herbicide Clomazone in the Earthworms Eisenia fetida. Bull Environ Contam Toxicol. 2015 Nov;95(5):606-10. doi: 10.1007/s00128-015-1649-7. Epub 2015 Sep 14. PubMed PMID: 26370279. 3: Darwish M, Vidal V, Lopez-Lauri F, Alnaser O, Junglee S, El Maataoui M, Sallanon H. Tolerance to clomazone herbicide is linked to the state of LHC, PQ-pool and ROS detoxification in tobacco (Nicotiana tabacum L.). J Plant Physiol. 2015 Mar 1;175:122-30. doi: 10.1016/j.jplph.2014.11.009. Epub 2014 Dec 12. PubMed PMID: 25544589. 4: Menezes C, Leitemperger J, Murussi C, Toni C, Araújo Mdo C, Farias IL, Perazzo GX, Barbosa NV, Loro VL. Herbicide clomazone effects on δ-aminolevulinic acid activity and metabolic parameters in Cyprinus carpio. Bull Environ Contam Toxicol. 2014 Apr;92(4):393-8. doi: 10.1007/s00128-014-1229-2. Epub 2014 Feb 23. PubMed PMID: 24562457. 5: Peters LP, Carvalho G, Martins PF, Dourado MN, Vilhena MB, Pileggi M, Azevedo RA. Differential responses of the antioxidant system of ametryn and clomazone tolerant bacteria. PLoS One. 2014 Nov 7;9(11):e112271. doi: 10.1371/journal.pone.0112271. eCollection 2014. PubMed PMID: 25380132; PubMed Central PMCID: PMC4224425. 6: Darwish M, Lopez-Lauri F, El Maataoui M, Urban L, Sallanon H. Pretreatment with alternation of light/dark periods improves the tolerance of tobacco (Nicotiana tabacum) to clomazone herbicide. J Photochem Photobiol B. 2014 May 5;134:49-56. doi: 10.1016/j.jphotobiol.2014.03.013. Epub 2014 Mar 29. PubMed PMID: 24792474. 7: Tomco PL, Holmes WE, Tjeerdema RS. Biodegradation of clomazone in a California rice field soil: carbon allocation and community effects. J Agric Food Chem. 2013 Mar 20;61(11):2618-24. doi: 10.1021/jf304692c. Epub 2013 Mar 6. PubMed PMID: 23432155. 8: de Oliveira CR, Fraceto LF, Rizzi GM, Salla RF, Abdalla FC, Costa MJ, Silva-Zacarin EC. Hepatic effects of the clomazone herbicide in both its free form and associated with chitosan-alginate nanoparticles in bullfrog tadpoles. Chemosphere. 2016 Apr;149:304-13. doi: 10.1016/j.chemosphere.2016.01.076. Epub 2016 Feb 10. PubMed PMID: 26874058. 9: Włodarczyk M, Siwek H. Influence of Formulation on Mobility of Clomazone in Soil. Bull Environ Contam Toxicol. 2016 Oct;97(4):582-7. doi: 10.1007/s00128-016-1903-7. Epub 2016 Aug 24. PubMed PMID: 27557602; PubMed Central PMCID: PMC5025482. 10: Darwish M, Lopez-Lauri F, Vidal V, El Maâtaoui M, Sallanon H. Alternation of light/dark period priming enhances clomazone tolerance by increasing the levels of ascorbate and phenolic compounds and ROS detoxification in tobacco (Nicotiana tabacum L.) plantlets. J Photochem Photobiol B. 2015 Jul;148:9-20. doi: 10.1016/j.jphotobiol.2015.03.017. Epub 2015 Mar 30. PubMed PMID: 25863439. 11: Murussi CR, Costa M, Menezes C, Leitemperger J, Guerra L, Lópes T, Severo E, Zanella R, Loro VL. Integrated assessment of biomarker response in carp (Cyprinus carpio) and silver catfish (Rhamdia quelen) exposed to clomazone. Arch Environ Contam Toxicol. 2015 May;68(4):646-54. doi: 10.1007/s00244-015-0145-8. Epub 2015 Mar 17. PubMed PMID: 25779373. 12: Menezes C, Leitemperger J, Toni C, Santi A, Lópes T, Barbosa NB, Neto JR, Loro VL. Comparative study on effects of dietary with diphenyl diselenide on oxidative stress in carp (Cyprinus carpio) and silver catfish (Rhamdia sp.) exposed to herbicide clomazone. Environ Toxicol Pharmacol. 2013 Sep;36(2):706-14. doi: 10.1016/j.etap.2013.07.002. Epub 2013 Jul 10. PubMed PMID: 23892285. 13: Tomco PL, Tjeerdema RS. Photolytic versus microbial degradation of clomazone in a flooded California rice field soil. Pest Manag Sci. 2012 Aug;68(8):1141-7. doi: 10.1002/ps.3275. Epub 2012 Mar 28. PubMed PMID: 22461377. 14: Fan X, Hu GS, Li N, Han ZF, Jia JM. Effects of lovastatin, clomazone and methyl jasmonate treatment on the accumulation of purpurin and mollugin in cell suspension cultures of Rubia cordifolia. Chin J Nat Med. 2013 Jul;11(4):396-400. doi: 10.1016/S1875-5364(13)60058-8. PubMed PMID: 23845549. 15: Benincá C, Vargas FT, Martins ML, Gonçalves FF, Vargas RP, Freire FB, Zanoelo EF. Removal of clomazone herbicide from a synthetic effluent by electrocoagulation. Water Sci Technol. 2016;73(12):2944-52. doi: 10.2166/wst.2016.133. PubMed PMID: 27332840. 16: Brum A, Dotta G, Roumbedakis K, Gonçalves EL, Garcia LP, Garcia P, Scussel VM, Martins ML. Hematological and histopathological changes in silver catfish Rhamdia quelen (Siluriformes) exposed to clomazone herbicide in the Madre River, Santa Catarina State, Southern Brazil. J Environ Sci Health B. 2014;49(3):169-75. doi: 10.1080/03601234.2014.858007. PubMed PMID: 24380617. 17: Abramović BF, Despotović VN, Šojić DV, Orčić DZ, Csanádi JJ, Četojević-Simin DD. Photocatalytic degradation of the herbicide clomazone in natural water using TiO2: kinetics, mechanism, and toxicity of degradation products. Chemosphere. 2013 Sep;93(1):166-71. doi: 10.1016/j.chemosphere.2013.05.024. Epub 2013 Jun 15. PubMed PMID: 23773444. 18: Yasuor H, Zou W, Tolstikov VV, Tjeerdema RS, Fischer AJ. Differential oxidative metabolism and 5-ketoclomazone accumulation are involved in Echinochloa phyllopogon resistance to clomazone. Plant Physiol. 2010 May;153(1):319-26. doi: 10.1104/pp.110.153296. Epub 2010 Mar 5. PubMed PMID: 20207709; PubMed Central PMCID: PMC2862431. 19: Gunasekara AS, dela Cruz ID, Curtis MJ, Claassen VP, Tjeerdema RS. The behavior of clomazone in the soil environment. Pest Manag Sci. 2009 Jun;65(6):711-6. doi: 10.1002/ps.1733. PubMed PMID: 19319928. 20: Feng Y, Liu J, Zhu L, Wei J. Combined technology for clomazone herbicide wastewater treatment: three-dimensional packed-bed electrochemical oxidation and biological contact degradation. Water Sci Technol. 2013;68(1):257-60. doi: 10.2166/wst.2013.162. PubMed PMID: 23823563.