3268. Diniconazole

Nomenclature

CAS number: 83657-24-3
(βE)-β-[(2,4-Dichlorophenyl)methylene]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol; (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol; S-3308-10; S-3308L; XE-779L; Ortho Spotless (Ortho); Spotless (Sumitomo); Sumi-8 (Sumitomo).
C15H17Cl2N3O; mol wt 326.22.
C 55.23%, H 5.25%, Cl 21.74%, N 12.88%, O 4.90%.

Description and references

Prepn: Y. Funaki et al., DE 3010560; eidem, US 4554007; resolution of enantiomers: Y. Funaki et al., EP 54431; eidem, US 4435203 (1980, 1985, 1982, 1984 all to Sumitomo). Metabolism of racemate in rats: N. Isobe et al., Nippon Noyaku Gakkaishi 10, 475 (1985), C.A. 104, 103703b (1986); of enantiomers: eidem, ibid. 12, 421 (1987), C.A. 108, 1715x (1988). Mechanism of sterol inhibition: Y. Yoshida et al., Biochem. Biophys. Res. Commun. 137, 513 (1986); T. Katagi, J. Agric. Food Chem. 36, 344 (1988). Fungicidal activity of the (-)-form and plant growth regulating activity of the (+)-form: C. S. Kvien et al., J. Plant Growth Regul. 6, 233 (1987); D. J. Daigle et al., Proc. 14th Ann. Mtg. Plant Growth Regul. Soc. Am. 1987, p 108. Field trials as foliar fungicide: A. R. Biggs, J. Warner, Can. J. Plant Pathol. 9, 41 (1987); A. K. Hagan et al., J. Environ. Hort. 6, 67 (1988); against soil-borne diseases: A. S. Csinos et al., Appl. Agric. Res. 2, 113 (1987). Comprehensive description: H. Takano, Jpn. Pestic. Inf. 49, 18 (1986).

Chemical structure

Properties

Crystals from isopropanol, mp 148-149°. Vapor pressure at 20°: 2.2 × 10-5 mm Hg. Soly at 25° (% v/w): water 4.01; at 23°: acetone 9.5; methanol 9.5; xylene 1.4. Stable to heat, sunlight and moisture. LD50 in male, female rats (mg/kg): 639, 474 orally; >5000, >5000 dermally (Takano).

Derivative

(-)-Form.

Nomenclature

CAS number: 83657-18-5

Properties

Crystals from carbon tetrachloride/n-hexane, mp 160-161°. [α]D24 -31.7° (c = 1 in CHCl3).

Derivative

(+)-Form.

Nomenclature

CAS number: 83657-19-6

Properties

Crystals from carbon tetrachloride/n-hexane, mp 160-161°. [α]D24 +26° (c = 1 in CHCl3).

Use

Agricultural fungicide.