4856. Hymexazol

Nomenclature

CAS number: 10004-44-1
5-Methyl-3(2H)-isoxazolone; 3-hydroxy-5-methylisoxazole; F-319; RTY-319; Tachigaren (Sankyo).
C4H5NO2; mol wt 99.09.
C 48.48%, H 5.09%, N 14.14%, O 32.29%.

Description and references

Prepn: NL 6511925; I. Iwai et al., US 3544584 (1966, 1970 both to Sankyo); I. Iwai, N. Nakamura, Chem. Pharm. Bull. 14, 1277 (1966). Metabolism in plants: S. Kamimura et al., Phytopathology 64, 1273 (1974). Properties and analytical methods: T. Nakamura et al., Anal. Methods Pestic. Plant Growth Regul. 10, 215 (1978). GC determn in plants and soils: idem et al., Annu. Rep. Sankyo Res. Lab. 28, 130 (1976). Plant growth promoting activity: Y. Ota, Jpn. Agric. Res. Q. 9, 1 (1975). Mode of fungicidal action: T. Nakanishi, H. D. Sisler, J. Pestic. Sci. 8, 173 (1983). Field studies: P. A. Payne, G. E. Williams, Crop Prot. 9, 371 (1990). Series of articles on chemistry, biological activity and metabolism: Annu. Rep. Sankyo Res. Lab. 25, 1-51 (1973). Brief review: R. Ishitsuka, Jpn. Pestic. Inf. 18, 27-30 (1974).

Chemical structure

Properties

White needles from n-hexane, mp 84-85°. Also reported as mp 86-87° (Nakamura, 1983). Vapor pressure (25°) 1.01 × 103 Torr. Soly at 25° (g/100 ml): ≈8.5 in water. Very sol in methanol, ethanol, isopropanol, acetone, methyl isobutyl ketone, tetrahydrofuran, dioxane, DMF, ethylene glycol, chloroform. Fairly sol in diethyl ether, benzene, xylene, trichloroethylene. Slightly sol in n-hexane, carbon disulfide. LD50 in male, female mice, rats (mg/kg): 2148, 1968, 4678, 3909 orally; 1297, 1167, 1924, 1884 s.c.; 445, 514, >1000, >1000 i.v.; in rats, rabbits (mg/kg): >10000, >2000 dermally (Nakamura, 1978).

Use

Agricultural fungicide and plant growth regulator.