1827. Carboxin

Nomenclature

CAS number: 5234-68-4
5,6-Dihydro-2-methyl-N-phenyl-1,4-oxathiin-3-carboxamide; 2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin; carbathiin; DCMO; Vitavax (Uniroyal).
C12H13NO2S; mol wt 235.30.
C 61.25%, H 5.57%, N 5.95%, O 13.60%, S 13.63%.

Description and references

Systemic fungicide, effective against loose smut in cereals. Prepn: B. von Schmeling et al., US 3249499 (1966 to U.S. Rubber); M. Kulka et al., US 3393202 (1968 to Uniroyal). Fungicidal activity: B. von Schmeling, M. Kulka, Science 152, 659 (1966). Inhibitor of succinate oxidation: D. E. Mathre, Phytopathology 60, 671 (1970); G. A. White, Biochem. Biophys. Res. Commun. 44, 1212 (1971); P. C. Mowery et al., ibid. 71, 354 (1976). Residue determn in crops: J. R. Lane, J. Agric. Food Chem. 18, 409 (1970); H. R. Sisken, J. E. Newell, ibid. 19, 738 (1971). Toxicity studies: T. V. Dyadicheva, Gig. Tr. Prof. Zabol. 1979(2), 55, C.A. 90, 146673b (1979).

Chemical structure

Properties

Crystals, from ethanol or methanol, mp 93-95°. LD50 in rats, mice (mg/kg): 430, 3200 orally (Dyadicheva).

Use

Systemic plant fungicide.