Carboxin
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| Category | Others |
| Catalog number | BBF-03892 |
| CAS | 5234-68-4 |
| Molecular Weight | 235.30 |
| Molecular Formula | C12H13NO2S |
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Description
Carboxin is an aniline fungicide used in agriculture to sow before sowing to protect seeds from disease.
Specification
| Synonyms | Carbathiin; Carboxine; Vitavax; Oxatin; 2-Methyl-N-Phenyl-5,6-Dihydro-1,4-Oxathiine-3-Carboxamide |
| Shelf Life | Limited shelf life, expiry date on the label |
| Storage | Store at -20°C |
| IUPAC Name | 6-methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide |
| Canonical SMILES | CC1=C(SCCO1)C(=O)NC2=CC=CC=C2 |
| InChI | 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) |
| InChI Key | GYSSRZJIHXQEHQ-UHFFFAOYSA-N |
Properties
| Appearance | Off-white Solid |
| Application | Pesticide |
| Boiling Point | 420.6°C at 760 mmHg |
| Melting Point | 91.1-91.7°C |
| Density | 1.45 g/cm3 |
| Solubility | Soluble in DMSO |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity | Not Likely to be Carcinogenic to Humans. |
Reference Reading
1. The carboxin-binding site on Paracoccus denitrificans succinate:quinone reductase identified by mutations
M Matsson, L Hederstedt J Bioenerg Biomembr . 2001 Apr;33(2):99-105. doi: 10.1023/a:1010744330092.
Succinate:quinone reductase catalyzes electron transfer from succinate to quinone in aerobic respiration. Carboxin is a specific inhibitor of this enzyme from several different organisms. We have isolated mutant strains of the bacterium Paracoccus denitrificans that are resistant to carboxin due to mutations in the succinate:quinone reductase. The mutations identify two amino acid residues, His228 in SdhB and Asp89 in SdhD, that most likely constitute part of a carboxin-binding site. This site is in the same region of the enzyme as the proposed active site for ubiquinone reduction. From the combined mutant data and structural information derived from Escherichia coli and Wolinella succinogenes quinol:fumarate reductase, we suggest that carboxin acts by blocking binding of ubiquinone to the active site. The block would be either by direct exclusion of ubiquinone from the active site or by occlusion of a pore that leads to the active site.
2. Carboxin and its major metabolites residues in peanuts: Levels, dietary intake and chronic intake risk assessment
Jun Xu, Yongquan Zheng, Mingshan Ji, Fengshou Dong, Xingang Liu, Xiaohu Wu, Dongmei Wei Food Chem . 2019 Mar 1;275:169-175. doi: 10.1016/j.foodchem.2018.09.087.
We developed an ultra-performance liquid chromatography-tandem mass spectral method to determine the fungicide carboxin and its metabolites, oxycarboxin and carboxin sulfoxide in peanut samples. The method was used to detect the concentration of the analytes in the samples from fields and markets. The total residue quantities in peanut kernels were used to evaluate the chronic dietary risk of total carboxin upon peanut consumption. The estimated dietary intake of carboxin from peanuts whose seeds had been treated with carboxin at the recommended dose was between 0.020% and 0.344% of acceptable daily intake and the risk was found to be negligible. The chronic dietary risk assessment from markets and commercial field samples for various groups of humans indicated that the group with the greatest degree of exposure was 45 to 75-year-old women who lived in rural areas. However, their acceptable daily intake percentage was 0.006%, meaning that their health risk was extremely small.
3. Inheritance of Carboxin Resistance in a European Field Isolate of Ustilago nuda
P L Thomas, G Newcombe Phytopathology . 2000 Feb;90(2):179-82. doi: 10.1094/PHYTO.2000.90.2.179.
ABSTRACT Two carboxin-resistant field isolates of Ustilago nuda from Europe were crossed with a carboxin-sensitive field isolate from North America. Meiotic tetrads isolated from germinating F(1) teliospores of one of the hybrids were tested for carboxin resistance and mating type. Carboxin resistance was shown to be controlled by a single gene (CBX1R), because a 1:1 segregation of carboxin resistance was observed in all 27 tetrads. Tetrad analysis indicated that the loci for carboxin resistance (Cbx1) and mating type (MAT1) segregate independently but may be located on the same chromosome. Tetrad analysis was not possible with the F(1) hybrid of he other field isolate, and its resistance cannot yet be attributed to CBX1R. Carboxin resistance was qualitatively dominant to sensitivity in vitro, as demonstrated by triad analysis of germinating F(1) teliospores. Quantitative in planta infection percents supported the conclusion that CBX1R is dominant, although incompletely, in the F(1) hybrid of one of the field isolates. Also, fewer than expected carboxin-sensitive F(2) individuals were observed in planta. However, inoculations of host plants with U. nuda have resulted in similar, unexpected variation in the past.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H13NO2S
Molecular Weight (Monoisotopic Mass): 235.0667 Da
Molecular Weight (Avergae Mass): 235.302 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C12H13NO2S
Molecular Weight (Monoisotopic Mass): 235.0667 Da
Molecular Weight (Avergae Mass): 235.302 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H13NO2S
Molecular Weight (Monoisotopic Mass): 235.0667 Da
Molecular Weight (Avergae Mass): 235.302 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C12H13NO2S
Molecular Weight (Monoisotopic Mass): 235.0667 Da
Molecular Weight (Avergae Mass): 235.302 Da
Mass Spectrum (Electron Ionization)
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
