Carboxin

Names

[ Name ]:
Carboxin

[Synonym ]:
2-Methyl-N-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
N3-Phenyl-2-methyl-5,6-dihydro-1,4-oxathiine-3-carboxamide
5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide
CARBOXIN
Vitavax 735D
6-methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide
2,3-dihydro-6-methyl-5-phenylcarbamyl-1,4-oxathiin
Vitavax 100
Carbathiine
MFCD00055403
EINECS 226-031-1
Carbathiin
5,6-Dihydro-2-methyl-1,4-oxathiine-3-carboxanilide
Vitavax 75W
1,4-Oxathiin-3-carboxamide, 5,6-dihydro-2-methyl-N-phenyl-
T6O DS BUTJ B1 CVMR
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin
5,6-Dihydro-3-methyl-N-phenyl-1,4-oxathin-2-carboxamide
Vitavax
Carboxine
DMOC
DCMO

Biological Activity

[Description]:

Carboxin (Carboxine) is a systemic agricultural fungicide and seed protectant.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[In Vitro]

Carboxin (Carboxine) is a systemic fungicide from the oxathiin class of agents. Carboxin demonstrates high specificity against the fungal class Basideomycetes, Deuteromycetes and Phycomycetes[1]. The systemic fungicide Carboxin is a powerful inhibitor of succinate oxidation in mitochondria[2].

[References]

[1]. Frampton CS, et al. Two polymorphic forms of the oxathiin systemic fungicide active carboxine. Acta Crystallogr E Crystallogr Commun. 2018 Nov 9;74(Pt 12):1741-1745.

[2]. G.A.White, et al. Oxathiin carboxamides highly active against carboxin-resistant succinic dehydrogenase complexes from carboxin-selected mutants of Ustilago maydis and Aspergillus nidulans. Pestic Biochem Physiol. 1978 Oct;9(2):165-182.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
420.6±45.0 °C at 760 mmHg

[ Melting Point ]:
91.1-91.7°C

[ Molecular Formula ]:
C₁₂H₁₃NO₂S

[ Molecular Weight ]:
235.302

[ Flash Point ]:
208.2±28.7 °C

[ Exact Mass ]:
235.066696

[ PSA ]:
63.63000

[ LogP ]:
3.00

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.636

[ Water Solubility ]:
10.095 g/100 mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RP4550000

CHEMICAL NAME :: 1,4-Oxathiin-3-carboxamide, 5,6-dihydro-2-methyl-N-phenyl-

CAS REGISTRY NUMBER :: 5234-68-4

BEILSTEIN REFERENCE NO. :: 0983249

LAST UPDATED :: 199701

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C12-H13-N-O2-S

MOLECULAR WEIGHT :: 235.32

WISWESSER LINE NOTATION :: T6O DS BUTJ B1 CVMR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 430 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >20 gm/m3/1H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1050 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3200 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 24 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Mammal - species unspecified

DOSE/DURATION :: 3200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - wild bird species

DOSE/DURATION :: 42200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 54300 ug/m3/4H/6W-I

TOXIC EFFECTS :: Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in leukocyte (WBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 161 gm/kg/2Y-I

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - fatty liver degeneration Blood - changes in erythrocyte (RBC) count

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 382 mg/kg/48H (Continuous)

REFERENCE :: EMMUEG Environmental and Molecular Mutagenesis. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.10- 1987- Volume(issue)/page/year: 12,235,1988 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 1 mg/m3;Skin JAN 1993

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xi,Xn

[ Risk Phrases ]:
R21/22

[ Safety Phrases ]:
36-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RP4550000

[ HS Code ]:
2934999038

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999038

[ Summary ]:
2934999038 2-methyl-n-phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide 4,4-dioxide。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

Articles

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Appl. Microbiol. Biotechnol. 70(6) , 735-9, (2006)

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Phototransformation of carboxin in water. Toxicity of the pesticide and its sulfoxide to aquatic organisms.

J. Agric. Food Chem. 52(20) , 6228-32, (2004)

Sunlight exposure of aqueous suspensions of carboxin (1) causes its phototransformation to sulfoxide 2 and minor components. Similar effects are observed in the presence of humic acid or nitrate or at...