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FRAC 11, C3 QoI; strobilurin type: methoxyacrylate

Common name azoxystrobin (BSI, E-ISO); azoxystrobine ((f) F-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]-α-(methoxymethylene)benzeneacetate CAS RN [131860–33–8], formerly [215934–32–0] Development codes ICIA5504 (ICI) Smiles code CO/C=C(/C(=O)OC)\c1ccccc1Oc2cc(Oc3ccccc3C#N)ncn2;without stereochemistry:COC=C(C(=O)OC)c1ccccc1Oc2cc(Oc3ccccc3C#N)ncn2
Composition >93%, with ≤2.5% (Z)- isomer (EU Rev. Rep.).
Mol. wt. 403.4 M.f. C22H17N3O5 Form White solid. M.p. 116ºC; (tech., 114–116ºC) B.p. decomp. 345ºC V.p. 1.1 &time; 10-7 mPa (20ºC) Kow logP = 2.5 (20ºC) Henry 7.3 &time; 10-9 Pa m3 mol-1 (calc.) S.g./density 1.34 (20ºC) Solubility In water 6 mg/l (20ºC). In hexane 0.057, n-octanol 1.4, methanol 20, toluene 55, acetone 86, ethyl acetate 130, acetonitrile 340, dichloromethane 400 (all in g/l, 20ºC). Stability DT50 for aqueous photolysis 2 w. Stable to hydrolysis at pH 5–7 and room temperature.
History Reported by J. R. Godwin et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1992, 1, 435). Introduced by Zeneca Agrochemicals (now Syngenta AG) and first marketed in 1996.
Patents EP 382375 Manufacturers Syngenta; Cheminova
Biochemistry Quinone outside inhibitor. 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/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; Elsinoë fawcettii, 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 GR; SC; SE; WG.
Selected products ' Amistar' (global) (Syngenta); ' Heritage' (USA, Japan) (Syngenta); ' Ortiva' (Europe, Africa, Middle East) (Syngenta); mixtures ' Quadris' (+ cymoxanil) (USA, Europe) (Syngenta). Other products ' Abound' (nuts and fruit) (Syngenta); ' Bankit' (bananas) (Syngenta); ' Priori' (vegetables, ornamentals, soya beans, coffee) (Syngenta); ' Landgold Strobilurin 250' (Teliton); ' Quo Vadis' (Herbos); mixtures ' Amistar Opti' (+ chlorothalonil) (Syngenta); ' Amistar Pro' (+ fenpropimorph) (cereals) (Syngenta); ' Amistar Top' (+ difenoconazole) (fruit, vegetables) (Syngenta); ' Amistar Xtra' (+ cyproconazole) (Syngenta); ' Dynasty' (+ fludioxonil + metalaxyl-M) (Syngenta); ' Olympus' (+ chlorothalonil) (cereals) (Syngenta); ' Priori Xtra' (+ cyproconazole) (Syngenta); ' Quilt' (+ propiconazole) (Syngenta); ' Renown' (+ chlorothalonil) (Syngenta); ' Amistar-Prince' (+ fipronil) (rice nursery box) (Nihon Nohyaku, Nissan, Syngenta); ' Seed Shield' (+ difenoconazole + fludioxonil + metalaxyl-M) (Helena). Discontinued products ' Gemstone' * (Syngenta); ' Protégé' * (Bayer CropScience, Gustafson); ' ZX' * (Barclay); mixtures ' Amistar Ter' * (+ hexaconazole) (cereals, peas) (Syngenta); ' Bravo Premium' * (+ propiconazole) (Europe, Africa, Middle East) (Syngenta); ' Cruiser Extreme' * (+ fludioxonil + metalaxyl-M + thiamethoxam) (Syngenta); ' CruiserMaxx Sunflower' * (+ fludioxonil + metalaxyl-M + thiamethoxam) (Syngenta); ' Amistar Admire' * (+ imidacloprid) (Bayer CropScience); ' Melody Star' * (+ iprovalicarb) (Germany, Italy, Portugal) (Bayer CropScience); ' Soygard' * (+ metalaxyl) (Bayer CropScience).
Residues by gc/NPD (Resid. Anal. Methods) or lc/ms/ms. Residues in water by hplc/uv (Environ. Chem. Methods). Residues in soil by hplc/uv, or by gc/ms (ibid.).
EU Rev. Rep. 7581/VI/97, Apr. 1998. EPA Fact Sheet, Feb. 1997. 91/414/EC Annex I status Included, 98/47/EC; renewed, 2008/656/EC.
Oral Acute oral LD50 for male and female rats and mice >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Slight eye and skin irritation (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h, nose only) for male rats 0.96, female rats 0.69 mg/l. NOEL (2 y) for rats 18 mg/kg b.w. daily. ADI/RfD (JMPR) 0.2 mg/kg b.w. [proposed]; (EC) 0.1 mg/kg b.w. [1998]; (EPA) RfD 0.18 mg/kg b.w. [1997]. Other Not genotoxic, carcinogenic or neurotoxic; azoxystrobin has no effect on fertility parameters nor on foetal or infant development. Toxicity Class WHO (a.i.) U. EC classification T; R23| N; R50, R53
Birds 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. Fish LC50 (96 h) for rainbow trout 0.47, bluegill sunfish 1.1, carp 1.6, sheepshead minnows 0.66 mg/l. Daphnia EC50 (48 h) 0.28 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 0.12 mg/l; EC50 (72 h) for diatom Navicula pelliculosa 0.014 mg/l. Other aquatic spp. LC50 (96 h) for mysid shrimps 0.055 mg/l; EC50 (48 h) for Pacific oysters 1.3 mg/l; EC50 (14 d) for Lemna gibba 3.2 mg/l; NOEC (25 d) for chironomid larvae 0.2 mg/l. Bees LD50 for honeybees (oral) >25 μg/bee; (contact) >200 μg/bee. Worms LC50 (14 d) for earthworms 283 mg/kg. Other beneficial spp. LR50 for predatory mites Typhlodromus pyri >1500 g/ha; LR50 for parasitoid wasps Aphidius rhopalosiphi >1000 g/ha.
Animals 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 Pestic. Chem. & Biosci.. Plants 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. Soil/Environment In soil, DT50 (lab.) 70 d (geometric mean; normalised to 20ºC, pF2; SFO kinetics). In soil, in the dark, up to six identified metabolites were formed; over 120 d, up to 27% of applied radiolabel is evolved as CO2. Dissipation in the field is faster; DT50 (geometric mean; SFO) 28 d, DT90 94 d (best fit, HS kinetics: DT50 13 d, DT90 236 d). On soil, photolysis DT50 11 d. Azoxystrobin is classified as moderately mobile in soil; average Kfoc for azoxystrobin c. 430. Field dissipation studies showed that neither azoxystrobin nor its major degradates were typically found in soil below the top 15 cm. In water-sediment systems (lab., 20ºC, dark), water phase ave. DT50 6.1 d (SFO), total system ave. DT50 214 d (SFO). Degradation in atmosphere occurs by reaction with hydroxyl radicals (AOP model), DT50 2.7 h.

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