Carboxin
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MedKoo CAT#: 581090

CAS#: 5234-68-4

Description: Carboxin is a systemic agricultural fungicide and seed treatment agent. Carboxin kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.


Chemical Structure

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Carboxin
CAS# 5234-68-4

Theoretical Analysis

MedKoo Cat#: 581090
Name: Carboxin
CAS#: 5234-68-4
Chemical Formula: C12H13NO2S
Exact Mass: 235.0667
Molecular Weight: 235.3
Elemental Analysis: C, 61.25; H, 5.57; N, 5.95; O, 13.60; S, 13.63

Price and Availability

Size Price Availability Quantity
5.0g USD 325.0 2 Weeks
25.0g USD 900.0 2 Weeks
50.0g USD 1325.0 2 Weeks
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Synonym: Carboxin; CCRIS 5217; Cerevax; D 735; D-735;D735;

IUPAC/Chemical Name: 2-methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide

InChi Key: GYSSRZJIHXQEHQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H13NO2S/c1-9-11(16-8-7-15-9)12(14)13-10-5-3-2-4-6-10/h2-6H,7-8H2,1H3,(H,13,14)

SMILES Code: O=C(Nc1ccccc1)C2=C(C)OCCS2

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

Preparing Stock Solutions

The following data is based on the product molecular weight 235.3 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

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1: Shima Y, Ito Y, Hatabayashi H, Koma A, Yabe K. Five carboxin-resistant mutants exhibited various responses to carboxin and related fungicides. Biosci Biotechnol Biochem. 2011;75(1):181-4. Epub 2011 Jan 7. PubMed PMID: 21228470.

2: Tucker AN, Lillich TT. Effect of the systemic fungicide carboxin on electron transport function in membranes of Micrococcus denitrificans. Antimicrob Agents Chemother. 1974 Nov;6(5):572-8. PubMed PMID: 15825307; PubMed Central PMCID: PMC444694.

3: Ngari C, Combier JP, Doré J, Marmeisse R, Gay G, Melayah D. The dominant Hc.Sdh (R) carboxin-resistance gene of the ectomycorrhizal fungus Hebeloma cylindrosporum as a selectable marker for transformation. Curr Genet. 2009 Apr;55(2):223-31. doi: 10.1007/s00294-009-0231-4. Epub 2009 Feb 13. PubMed PMID: 19214514.

4: Matsson M, Ackrell BA, Cochran B, Hederstedt L. Carboxin resistance in Paracoccus denitrificans conferred by a mutation in the membrane-anchor domain of succinate:quinone reductase. Arch Microbiol. 1998 Jul;170(1):27-37. PubMed PMID: 9639600.

5: Guo M, Zhu X, Li H, Tan L, Pan Y. Development of a novel strategy for fungal transformation based on a mutant locus conferring carboxin-resistance in Magnaporthe oryzae. AMB Express. 2016 Dec;6(1):57. doi: 10.1186/s13568-016-0232-x. Epub 2016 Aug 24. PubMed PMID: 27558019; PubMed Central PMCID: PMC4996803.

6: Kilaru S, Collins CM, Hartley AJ, Burns C, Foster GD, Bailey AM. Investigating dominant selection markers for Coprinopsis cinerea: a carboxin resistance system and re-evaluation of hygromycin and phleomycin resistance vectors. Curr Genet. 2009 Oct;55(5):543-50. doi: 10.1007/s00294-009-0266-6. Epub 2009 Jul 28. PubMed PMID: 19636558.

7: Topp CN, Ruiz-Herrera J, Martínez-Espinoza AD, Gold SE. Integration of the gene for carboxin resistance does not impact the Ustilago maydis-maize interaction. Curr Microbiol. 2002 Jan;44(1):67-70. PubMed PMID: 11727044.

8: Grivennikova VG, Vinogradov AD. [Interaction of mitochondrial succinate:ubiquinone reductase with thenoyltrifluoroacetone and carboxin]. Biokhimiia. 1985 Mar;50(3):375-83. Russian. PubMed PMID: 3995101.

9: Ruiz-Herrera J, Martinez-Espinoza AD, Alvarez PE, Xoconostle-Cazares B. Carboxin-resistant mutant of ustilago maydis is impaired in its pathogenicity for zea mays. Curr Microbiol. 1999 Nov;39(5):291-4. PubMed PMID: 10489439.

10: Keon JP, White GA, Hargreaves JA. Isolation, characterization and sequence of a gene conferring resistance to the systemic fungicide carboxin from the maize smut pathogen, Ustilago maydis. Curr Genet. 1991 Jun;19(6):475-81. PubMed PMID: 1879000.

11: Newcombe G, Thomas PL. Inheritance of Carboxin Resistance in a European Field Isolate of Ustilago nuda. Phytopathology. 2000 Feb;90(2):179-82. doi: 10.1094/PHYTO.2000.90.2.179. PubMed PMID: 18944606.

12: Lalève A, Gamet S, Walker AS, Debieu D, Toquin V, Fillinger S. Site-directed mutagenesis of the P225, N230 and H272 residues of succinate dehydrogenase subunit B from Botrytis cinerea highlights different roles in enzyme activity and inhibitor binding. Environ Microbiol. 2014 Jul;16(7):2253-66. doi: 10.1111/1462-2920.12282. Epub 2013 Oct 10. PubMed PMID: 24119086.

13: Broomfield PL, Hargreaves JA. A single amino-acid change in the iron-sulphur protein subunit of succinate dehydrogenase confers resistance to carboxin in Ustilago maydis. Curr Genet. 1992 Aug;22(2):117-21. PubMed PMID: 1423716.

14: Gunatilleke IA, Arst HN Jr, Scazzocchio C. Three genes determine the carboxin sensitivity of mitochondrial succinate oxidation in aspergillus nidulans. Genet Res. 1975 Dec;26(3):297-305. PubMed PMID: 178574.

15: Singh RB, Singh HK, Parmar A. Yield loss assessment due to Alternaria blight and its management in linseed. Pak J Biol Sci. 2014 Apr;17(4):511-6. PubMed PMID: 25911838.

16: Shima Y, Ito Y, Kaneko S, Hatabayashi H, Watanabe Y, Adachi Y, Yabe K. Identification of three mutant loci conferring carboxin-resistance and development of a novel transformation system in Aspergillus oryzae. Fungal Genet Biol. 2009 Jan;46(1):67-76. doi: 10.1016/j.fgb.2008.10.005. Epub 2008 Oct 21. PubMed PMID: 18992352.

17: Farrow JE, Hoodless RA, Hopkinson A. Fungicide residues. Part IV. Determination of residues of carboxin in grain by gas chromatography. Analyst. 1975 Apr;100(1189):249-52. PubMed PMID: 1137196.

18: Skinner W, Bailey A, Renwick A, Keon J, Gurr S, Hargreaves J. A single amino-acid substitution in the iron-sulphur protein subunit of succinate dehydrogenase determines resistance to carboxin in Mycosphaerella graminicola. Curr Genet. 1998 Dec;34(5):393-8. PubMed PMID: 9871122.

19: Iesce MR, Cermola F, De Lorenzo F, Graziano ML, Caliendo B. Photochemical behaviour of the systemic fungicide carboxin. Environ Sci Pollut Res Int. 2002;9(2):107-9. PubMed PMID: 12008289.

20: Honda Y, Matsuyama T, Irie T, Watanabe T, Kuwahara M. Carboxin resistance transformation of the homobasidiomycete fungus Pleurotus ostreatus. Curr Genet. 2000 Mar;37(3):209-12. PubMed PMID: 10794179.