Sulfometuron-methyl | CAS# 74222-97-2 | Herbicide

MedKoo Cat#: 571276 | Name: Sulfometuron-methyl

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Description:

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

Sulfometuron-methyl is a herbicide that also is an active antibacterial agent. Sulfometuron-methyl is a potent inhibitor of acetolactate synthase II and thus exhibits antibacterial properties.

Chemical Structure

Sulfometuron-methyl

CAS#74222-97-2

Theoretical Analysis

MedKoo Cat#: 571276

Name: Sulfometuron-methyl

CAS#: 74222-97-2

Chemical Formula: C15H16N4O5S

Exact Mass: 364.0841

Molecular Weight: 364.38

Elemental Analysis: C, 49.44; H, 4.43; N, 15.38; O, 21.95; S, 8.80

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 290.00

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Synonym

Sulfometuron-methyl; DXP 5648; DXP-5648; DXP5648

IUPAC/Chemical Name

Benzoic acid, 2-(((((4,6-dimethyl-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-, methyl ester

InChi Key

ZDXMLEQEMNLCQG-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H16N4O5S/c1-9-8-10(2)17-14(16-9)18-15(21)19-25(22,23)12-7-5-4-6-11(12)13(20)24-3/h4-8H,1-3H3,(H2,16,17,18,19,21)

SMILES Code

O=C(OC)C1=CC=CC=C1S(=O)(NC(NC2=NC(C)=CC(C)=N2)=O)=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

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

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Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 364.38 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

1: LaRossa RA, Smulski DR. ilvB-encoded acetolactate synthase is resistant to the herbicide sulfometuron methyl. J Bacteriol. 1984 Oct;160(1):391-4. PubMed PMID: 6090425; PubMed Central PMCID: PMC214730. 2: LaRossa RA, Schloss JV. The sulfonylurea herbicide sulfometuron methyl is an extremely potent and selective inhibitor of acetolactate synthase in Salmonella typhimurium. J Biol Chem. 1984 Jul 25;259(14):8753-7. PubMed PMID: 6378902. 3: Michael JL. Environmental fate and impacts of sulfometuron on watersheds in the southern United States. J Environ Qual. 2003 Mar-Apr;32(2):456-65. PubMed PMID: 12708668. 4: Yadav N, McDevitt RE, Benard S, Falco SC. Single amino acid substitutions in the enzyme acetolactate synthase confer resistance to the herbicide sulfometuron methyl. Proc Natl Acad Sci U S A. 1986 Jun;83(12):4418-22. PubMed PMID: 16593715; PubMed Central PMCID: PMC323744. 5: Ambrona J, Maqueda M, Zamora E, Ramírez M. Sulfometuron resistance as a genetic marker for yeast populations in wine fermentations. J Agric Food Chem. 2005 Sep 21;53(19):7438-43. PubMed PMID: 16159170. 6: Van Dyk TK, LaRossa RA. Sensitivity of a Salmonella typhimurium aspC mutant to sulfometuron methyl, a potent inhibitor of acetolactate synthase II. J Bacteriol. 1986 Feb;165(2):386-92. PubMed PMID: 3003025; PubMed Central PMCID: PMC214429. 7: Kaplun A, Chipman DM, Barak Z. Isoleucine starvation caused by sulfometuron methyl in Salmonella typhimurium measured by translational frameshifting. Microbiology. 2002 Mar;148(Pt 3):713-7. PubMed PMID: 11882705. 8: Maiti SN, Zink MW, Rank GH. Effect of valine and the herbicide sulfometuron methyl on acetolactate synthase activity in nuclear and plasmid-borne sulphometuron methyl resistant Saccharomyces cerevisiae strains. Can J Microbiol. 1988 May;34(5):680-5. PubMed PMID: 3061621. 9: Xing RY, Whitman WB. Sulfometuron methyl-sensitive and -resistant acetolactate synthases of the archaebacteria Methanococcus spp. J Bacteriol. 1987 Oct;169(10):4486-92. PubMed PMID: 3654579; PubMed Central PMCID: PMC213812. 10: Falco SC, Dumas KS. Genetic analysis of mutants of Saccharomyces cerevisiae resistant to the herbicide sulfometuron methyl. Genetics. 1985 Jan;109(1):21-35. PubMed PMID: 3881312; PubMed Central PMCID: PMC1202477. 11: Matchett WH, Winnik W, Betowski LO, Brumley WC. A kinetic study of the methanolysis of the sulfonylureas bensulfuron methyl and sulfometuron methyl using capillary electrophoresis. Electrophoresis. 1997 Feb;18(2):205-13. PubMed PMID: 9080127. 12: Mishael YG, Undabeytia T, Rytwo G, Papahadjopoulos-Sternberg B, Rubin B, Nir S. Sulfometuron incorporation in cationic micelles adsorbed on montmorillonite. J Agric Food Chem. 2002 May 8;50(10):2856-63. PubMed PMID: 11982411. 13: Mishael YG, Undabeytia T, Rabinovitz O, Rubin B, Nir S. Slow-release formulations of sulfometuron incorporated in micelles adsorbed on montmorillonite. J Agric Food Chem. 2002 May 8;50(10):2864-9. PubMed PMID: 11982412. 14: Dos Reis FC, Tornisielo VL, Pimpinato RF, Martins BA, Victória Filho R. Leaching of Diuron, Hexazinone, and Sulfometuron-methyl Applied Alone and in Mixture in Soils with Contrasting Textures. J Agric Food Chem. 2017 Apr 5;65(13):2645-2650. doi: 10.1021/acs.jafc.6b05127. Epub 2017 Mar 22. PubMed PMID: 28326783. 15: Hartnett ME, Newcomb JR, Hodson RC. Mutations in Chlamydomonas reinhardtii Conferring Resistance to the Herbicide Sulfometuron Methyl. Plant Physiol. 1987 Dec;85(4):898-901. PubMed PMID: 16665827; PubMed Central PMCID: PMC1054365. 16: Van Dyk TK, Smulski DR, Chang YY. Pleiotropic effects of poxA regulatory mutations of Escherichia coli and Salmonella typhimurium, mutations conferring sulfometuron methyl and alpha-ketobutyrate hypersensitivity. J Bacteriol. 1987 Oct;169(10):4540-6. PubMed PMID: 2820932; PubMed Central PMCID: PMC213819. 17: Kingsbury JM, Yang Z, Ganous TM, Cox GM, McCusker JH. Cryptococcus neoformans Ilv2p confers resistance to sulfometuron methyl and is required for survival at 37 degrees C and in vivo. Microbiology. 2004 May;150(Pt 5):1547-58. PubMed PMID: 15133116. 18: Azcarate MP, Montoya JC, Koskinen WC. Sorption, desorption and leaching potential of sulfonylurea herbicides in Argentinean soils. J Environ Sci Health B. 2015;50(4):229-37. doi: 10.1080/03601234.2015.999583. PubMed PMID: 25714454. 19: Jia MH, Larossa RA, Lee JM, Rafalski A, Derose E, Gonye G, Xue Z. Global expression profiling of yeast treated with an inhibitor of amino acid biosynthesis, sulfometuron methyl. Physiol Genomics. 2000 Aug 9;3(2):83-92. PubMed PMID: 11015603. 20: Xie Q, Jiménez A. Molecular cloning of a novel allele of SMR1 which determines sulfometuron methyl resistance in Saccharomyces cerevisiae. FEMS Microbiol Lett. 1996 Apr 1;137(2-3):165-8. PubMed PMID: 8998980.