4129. Fludioxonil

Nomenclature

CAS number: 131341-86-1
4-(2,2-Difluoro-1,3-benzodioxol-4-yl)-1H-pyrrole-3-carbonitrile; 3-(2,2-difluorobenzodioxol-4-yl)-4-cyanopyrrole; CGA-173506; Celest (Syngenta); Maxim (Syngenta); Medallion (Syngenta); Scholar (Syngenta).
C12H6F2N2O2; mol wt 248.19.
C 58.07%, H 2.44%, F 15.31%, N 11.29%, O 12.89%.

Description and references

Nonsystemic phenylpyrrole fungicide structurally related to pyrrolnitrin, q.v. Prepn: R. Nyfeler, J. Ehrenfreund, EP 206999; eidem, US 4705800 (1986, 1987 both to Ciba-Geigy). Field trial for postharvest control of blue mold in apples: D. Errampalli et al., Postharvest Biol. Technol. 39, 101 (2006). Efficacy and residue levels in stone fruit: S. D'Aquino et al., J. Agric. Food Chem. 55, 825 (2007). Comprehensive description: K. Gehmann et al., Brighton Crop Prot. Conf. - Pests Dis. 1990, 399-406. Review of field trials as seed treatment: E. Koch, A. J. Leadbeater, ibid. 1992, 1137-1146.

Chemical structure

Properties

Colorless, odorless crystals, mp 199.4°. Log P (n-octanol/water): 2.6. Vapor pressure (25°): 2.9×10.9 mmHg. Soly in water (25°): 1.8 mg/ml. LD50 in rats (mg/kg): >2000 orally; >2000 dermally; LC50 (4 hr) in rats: >2600 mg/m3 (Gehmann).

Use

Agricultural fungicide.