methyl (E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate

methyl (E)-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-a-(methoxymethylene)benzeneacetate

C₂₂H₁₇N₃O₅

White solid

116^oC; (tech., 114-116^oC)

1.1×10^-7 mPa (20^oC)

1.34 (20^oC)

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.

DT₅₀ for aqueous photolysis 2 w. Stable to hydrolysis..

2.5

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.

Fungicide with protectant, curative, eradicant, translaminar and systemic properties. Inhibits spore germination and mycelial growth, and also shows antisporulant activity.

Controls the following pathogens at application rates between 100 to 375 g/ha

Good crop safety, except on some varieties of apple

Acute oral LD₅₀ for male and female rats and mice >5000 mg/kg.   

Acute percutaneous LD₅₀ for rats >2000 mg/kg. Slight eye and skin irritation (rabbits). Not a skin sensitiser (guinea pigs).

LC₅₀ (4 h, nose only) for male rats 0.96, female rats 0.69 mg/l.

(2 y) for rats 18 mg/kg b.w. daily. 

0.1 mg/kg b.w. (EU); 0.18 mg/kg b.w. (USA) 

WHO (a.i.) U  EC classification T; R23| N; R50, R53

Acute oral LD₅₀ for mallard ducks and bobwhite quail >2000 mg/kg. Dietary LC₅₀ (5 d) for bobwhite quail and mallard ducks >5200 mg/kg diet.

LC₅₀ (96 h) for rainbow trout 0.47, bluegill sunfish 1.1, carp 1.6, sheepshead minnow 0.66 mg/l. For degradate R234886, LC₅₀ >150 mg/l.

EC₅₀ (48 h) 80 ug/l. EC₅₀ for degradates: R234886 >180, R401553 >50, R402173 >50 mg/l.

EC₅₀ (120 h) for Selenastrum capricornutum 0.12 mg/l.

LC₅₀ (14 d) for earthworms 283 mg/kg.

In wheat, grapes and peanuts, metabolism was extensive, but parent azoxystrobin was the only major (>10%) residue. Metabolism followed similar pathways in all three crops.

In rats, the majority of radiolabel is excreted in the faeces, with little remaining radioactivity in any tissues of the animal. A large number of metabolites was formed, of which only the glucuronide of azoxystrobin acid is present at >10% of the administered dose. In goats and hens, azoxystrobin is also excreted rapidly, with low residues in milk, meat or eggs. For details, see R. S. I. Joseph in "Pesticide Chemistry and Bioscience".

Average DT₅₀ (lab.) 8 w (20^oC, pF 2). In soil, in the dark, six identified metabolites were formed; over 1 y, 45% of applied radiolabel is evolved as CO₂. Dissipation in the field is faster, average DT₅₀ 2 w, DT₉₀ 41 w. On soil, photolysis DT5₅₀ 11 d. Azoxystrobin and its degradates have low to moderate mobility in soil; typical Koc for azoxystrobin c. 500. Field dissipation studies showed that neither azoxystrobin nor its major degradates were typically found in soil below the top 15 cm. 

Residues in water by hplc with fluorescence detection