Azoxystrobin 嘧菌酯

嘧菌酯

基本信息
英文名称：Azoxystrobin，
CAS号：131860-33-8， 嘧菌酯结构式
化学名称为methyl(αE)2-2-[[6-(2-cyanophenoxy)-4-pyrimidinyl]oxy]-α-(methoxymethylene)benzeneacetate，
中文名称为：（E)2-[2-[6-(2-氰基苯氧基)嘧啶-4-基氧]苯基]-3-甲氧基丙烯酸甲酯
分子式为C22H17N3O5，分子量为403.4。

理化性质及用途
商品名为Abound、Amistar、Heritage、Quadris、Admire。 恶霜菌酯
]纯品为白色结晶固体，M.P.116℃。相对密度1.34，蒸汽压1.1×10-7mPa（20℃）。水中溶解度6mg/L（20℃），微溶于己烷、正辛醇，溶于甲醇、甲苯、丙酮，易溶于乙酸乙酯、乙腈、二氯甲烷。水溶液中光解半衰期为2周，对水解稳定。原药为棕色固体。该产品是甲氧基丙烯酸酯(Strobilurin)类杀菌剂，高效、广谱，对几乎所有的真菌界（子囊菌亚门、担子菌亚门、鞭毛菌亚门和半知菌亚门）病害如白粉病、锈病、颖枯病、网斑病、霜霉病、稻瘟病等均有良好的活性。可用于茎叶喷雾、种子处理，也可进行土壤处理，主要用于谷物、水稻、花生、葡萄、马铃薯、果树、蔬菜、咖啡、草坪等。使用剂量为25ml-50/亩。嘧菌酯与二甲苯可产生化学反应，影响药效，乳油剂型农药大部分含二甲苯，所以嘧菌酯不宜与乳油剂型农药混用。

毒性：
大鼠、小鼠急性经口LD50(雄、雌)：>5000mg/kg； 大鼠急性经皮LD50：>2000mg/109kg；本品对兔眼睛和皮肤轻微刺激。无致畸、致突变、致癌作用。鹌鹑经口 D50：>2000mg/kg；亚急性毒性(鹌鹑、野鸭)LC50：>5200mg/kg。 在推荐剂量下于田间施用对其它非靶标生物均无不良影响。
制剂： SC，W G。

作用机理： 线粒体呼吸抑制剂即通过在细胞色素b和C1间电子转移抑制线粒体的呼吸。对14-脱甲基化酶抑制剂、苯甲酰胺类、二羧酰胺类和苯并咪唑类产生抗性的菌株有效。具有保护、治疗、铲除、渗透、内吸活性。

适宜作物： 谷物、水稻、葡萄、马铃薯、蔬菜、果树等
对作物安全性： 推荐剂量下对作物安全、无药害
防治对象： 几乎所有真菌纲(子囊菌纲、担子菌纲、卵菌纲和半知菌类)病害如白粉病、锈病、颍枯病、网斑病、黑腥病、霜霉病、稻瘟病等

应用： ICI-A5504是新型高效、广谱、内吸性杀菌剂。可用于茎叶喷雾、种子处理，也可进行土壤处理。其对几乎所有真菌纲(子囊菌纲、担子菌纲、卵菌纲和半知菌类)病害如白粉病、锈病、颍枯病、网斑病、霜霉病、稻瘟病等均有良好的活性且与目前已有杀菌剂无交互抗性。用于谷物、水稻、葡萄、马铃薯、蔬菜、果树及其它作物，对这些作物安全。施用剂量根据作物和病害的不同为25~400克有效成分/公顷。
在25克有效成分/百升剂量下，对葡萄霜霉病有很好的预防作用；在12.5克有效成分/百升剂量下，对葡萄白粉病有很好的防治效果；在200克有效成分/公顷剂量下，对马铃薯疫病有预防作用；在12.5毫克有效成分/升剂量下，对苹果黑腥病有很好的防治效果，活性优于氟硅唑。

azoxystrobin
Fungicide
FRAC 11, C3; 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] formerly [215934-32-0] 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) 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.

COMMERCIALISATION
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

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/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; Elsino?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 SC; WG.; GR; SE. Selected products: 'Amistar' (not USA) (Syngenta); 'Heritage' (USA, Japan) (Syngenta); 'ZX' (Barclay); mixtures: 'Quadris' (+ cymoxanil) (Syngenta); 'Amistar Admire' (+ imidacloprid) (Bayer CropScience)

OTHER PRODUCTS
'Abound' (nuts and fruit) (Syngenta); 'Bankit' (bananas) (Syngenta); 'Gemstone' (Syngenta); 'Olympus' (Syngenta); 'Ortiva' (vegetables) (Syngenta); 'Priori' (vegetables, ornamentals, soya beans, coffee) (Syngenta); 'Landgold Strobilurin 250' (Landgold); 'Protege' (Gustafson) mixtures: 'Amistar Pro' (+ fenpropimorph) (cereals) (Syngenta); 'Amistar Ter' (+ hexaconazole) (cereals, peas) (Syngenta); 'Amistar-Prince' (+ fipronil) (rice nursery box) (Syngenta, Nihon Nohyaku, Nissan); 'Melody Star' (+ iprovalicarb) (Germany, Italy, Portugal) (Bayer CropScience)

ANALYSIS
Residues in water by hplc with fluorescence detection (T. J. Meyers & P. D. Francis, Proc. 9th IUPAC Int. Congr. Pestic. Chem., London (1998), 2, 7C-010).

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

ECOTOXICOLOGY
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 minnow 0.66 mg/l. For degradate R234886, LC50 >150 mg/l. Daphnia EC50 (48 h) 80 mg/l. EC50 for degradates: R234886 >180, R401553 >50, R402173 >50 mg/l. Algae EC50 (120 h) for Selenastrum capricornutum 0.12 mg/l. Other aquatic spp. LC50 (96 h) for mysid shrimp 55 mg/l; EC50 (48 h) for pacific oyster 1300 mg/l; EC50 (14 d) for Lemna gibba 3.2 mg/l. Bees LD50 for honeybees (oral) >25 mg/bee; (contact) >200 mg/bee. Worms LC50 (14 d) for earthworms 283 mg/kg. Other beneficial spp. Harmless to non-target organisms, including predatory mites and bugs, spiders, lacewings, hoverfly, ladybird, carabid beetle, parasitoid wasps and bees, under field conditions at field application rates (IOBC); e.g. LR50 (7 d) for Typhlodromus pyri >1500 g/ha; LR50 (48 h) for Aphidius rhopalosiphi >1135 g/ha.

ENVIRONMENTAL FATE
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 "Pesticide Chemistry and Bioscience". 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 Average DT50 (lab.) 8 w (20 °C, 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 DT50 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.