5934. Metconazole

Nomenclature

CAS number: 125116-23-6
5-[(4-Chlorophenyl)methyl]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol; (1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol; Caramba (BASF).
C17H22ClN3O; mol wt 319.83.
C 63.84%, H 6.93%, Cl 11.08%, N 13.14%, O 5.00%.

Description and references

Broad spectrum triazole antifungal; mixture of two racemic diastereomers. Prepn: S. Kumazawa et al., EP 267778; eidem, US 4938792 (1987, 1990 both to Kureha); and structure activity study: A. Ito et al., J. Pestic. Sci. 24, 262 (1999). Efficacy in wheat and barley: B. T. Grayson et al., Pestic. Sci. 45, 153 (1995); A. J. Sampson et al., ibid. 161. Review: idem et al., Brighton Crop Prot. Conf. - Pests Dis. 1992, 419-426.

Chemical structure

Derivative

cis-Form.

Nomenclature

CAS number: 115850-27-6
WL-136184.

Description and references

Mixture of (1R,5S) and (1S,5R) isomers and is more bioactive than the trans form.

Properties

Colorless crystals from hexane-ethyl acetate, mp 113-114°. Soly in water: 15 mg/kg.

Derivative

trans-Form.

Nomenclature

CAS number: 115850-28-7

Properties

mp 90-92°.

Use

Agricultural fungicide.