924. Azoxystrobin

Nomenclature

CAS number: 131860-33-8
(αE)-2-[[6-(2-Cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene)benzeneacetic acid methyl ester; methyl (E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate; ICI-A-5504; Amistar (Syngenta); Heritage (Syngenta); Quadris (Syngenta).
C22H17N3O5; mol wt 403.39.
C 65.50%, H 4.25%, N 10.42%, O 19.83%.

Description and references

Strobilurin fungicide; inhibits mitochondrial respiration by blocking electron transfer between cytochromes b and c1. Prepn: J. M. Clough et al., EP 382375 (1990 to I.C.I.); eidem, US 5395837 (1995 to Zeneca). Comprehensive description: J. R. Godwin et al., Brighton Crop Prot. Conf. - Pests Dis. 1992, 435-442. Field trials in turfgrass: J. A. Frank, P. L. Sanders, ibid. 1994, 871. Environmental fate: E. D. Pilling et al., ibid. 1996, 315.

Chemical structure

Properties

White crystalline solid, mp 118-119°. d 1.33. Partition coefficient (n-octanol/water): 440. Vapor pressure (20°): <105 Pa. Soly in water (25°): 10 mg/l. LD50 in rats (mg/kg): >5000 orally; >2000 dermally (Godwin).

Use

Agricultural fungicide.