Products

 

AZOXYSTROBIN

 

Fungicide
FRAC  11; strobilurin type: methoxyacrylate
Synthetic analogue of naturally occurring fungal metabolites the strobilurins and oudemansins.


NOMENCLATURE
Common name azoxystrobin (BSI, pa ISO)
IUPAC name methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate 
Chemical Abstracts name methyl (E)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a-(methoxymethylene)benzeneacetate 
CAS RN [131860-33-8]  Development codes ICIA5504 (ICI)

PHYSICAL CHEMISTRY
Mol. wt. 403.4  M.f. C22H17N3O5 Form White solid.  M.p. 116 °C (tech., 114-116 °C)  V.p. 1.1 × 10-7 mPa (20 °C)  KOW logP = 2.5 (20 °C)  Henry 7.3 × 10-9 Pa m3 mol-1 (calc.)  S.g./density 1.34 (20 °C)  Solubility In water 6 mg/l (20 ºC). Low solubility in hexane, n-octanol; moderate solubility in methanol, toluene, acetone; high solubility in ethyl acetate, acetonitrile, dichloromethane.  Stability DT50 for aqueous photolysis 2 w. Stable to hydrolysis. 

APPLICATIONS
Biochemistry Inhibits mitochondrial respiration by blocking electron transfer between cytochrome b and cytochrome c1, at the ubiquinol oxidising site. Controls pathogenic strains resistant to the 14-demethylase inhibitors, phenylamides, dicarboxamides or benzimidazoles.  Mode of action Fungicide with protectant, curative, eradicant, translaminar and systemic properties. Inhibits spore germination and mycelial growth, and also shows antisporulant activity.  Uses Controls the following pathogens at application rates between 100 to 375 g a.i./ha: Erysiphe graminis, Puccinia spp., Leptosphaeria nodorum, Septoria tritici and Pyrenophora teres on temperate cereals; Pyricularia oryzae and Rhizoctonia solani on rice; Plasmopara viticola and Uncinula necator on vines; Sphaerotheca fuliginea and Pseudoperonospora cubensis on cucurbitaceae; Phytophthora infestans and Alternaria solani on potato and tomato; Mycosphaerella arachidis, Rhizoctonia solani and Sclerotium rolfsii on peanut; Monilinia spp. and Cladosporium carpophilum on peach; Pythium spp. and Rhizoctonia solani on turf; Mycosphaerella spp. on banana; Cladosporium caryigenum on pecan; Elsinofawcettii, Colletotrichum spp. and Guignardia citricarpa on citrus; Colletotrichum spp. and Hemileia vastatrix on coffee.  Phytotoxicity Good crop safety, except on some varieties of apple (e.g. McIntosh, Cox).  Formulation types SC, WG.