Tetraconazole 氟醚唑,四氟咪唑

氟醚唑

【中文名称】氟醚唑；（±）-2-（2，4-二氯苯基）-3-（1H-1，2，4-三唑-1-基）丙基-1，1，2，2，-四氟乙基醚
【英文名称】tetraconazole;(±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl-1,1,2,2-te-trafluoroethyl ether;(±)-1-(2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)Propyl)-1H-1,2,4-triazole
【相对分子量或原子量】372.1
【蒸气压（Pa）】1.6mPa(20℃)
【毒性LD50(mg/kg)】
大鼠急性经口 LD50： 1250（雄）、 1031（雌），大鼠急性经皮LD50>2000，对大鼠无致突变性，在Ames试验中无诱变性。鱼毒LC50（96h，mg/L）：蓝鳃鱼4.0，虹蹲鱼4.8。
【性状】
纯品为粘稠油状物
【溶解情况】
溶解度（20℃）:水150mg/L，可与丙酮、二氯甲烷、甲醇互溶。
【用途】
本品属三唑类杀菌剂。是甾醇脱甲基化抑制剂。用于禾谷类作物和甜菜作叶面喷雾[100～125g（a.i.）/ha]，用于葡萄、观赏植物、仁果、核果、蔬菜作叶面喷雾（20～50g/ha），也可作种子处理（10～30g/100kg种子）。对禾谷类作物、葡萄、观赏植物、仁果、核果、甜菜和蔬菜上的白粉菌、禾谷类作物上的柄锈菌，蔬菜上的单胞锈菌，甜菜上的甜菜生尾孢和仁果上的黑星菌均有效。
【制备或来源】
以取代的羟基羧酸酯为原料，经一系列反应制得氟醚唑，
55%氢化钠(0.4g)油状悬浮液在氮气保护下分散在10ml无水二甲基甲酰胺中，于室温下，加入溶于10ml二甲基甲酰中的2-(2,4-二氯苯基)-3-(1H-1，2，4-三唑-1-基)丙醇2.4g，约30分钟后反应毕，将反应混合物冷却至0℃，通入四氟乙烯，将流量控制在使反应温度不超过30℃，反应毕将反应混合到入水中，用氯仿抽提，用水洗涤有机层，用无水硫酸钠干燥，减压蒸发，洗脱剂为正己烷-乙醚(8：2)，得无色粘稠油状物。
【其他】
稳定性；其水溶液对日光稳定，在PH5～9下水解，对铜有轻微腐蚀性。

tetraconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name tetraconazole (BSI, draft E-ISO)
IUPAC name (RS)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl 1,1,2,2-tetrafluoroethyl ether
Chemical Abstracts name (?-1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole
CAS RN [112281-77-3] unstated stereochemistry EEC no. 407-706-6 Development codes M 14360 (Agrimont)

PHYSICAL CHEMISTRY
Mol. wt. 372.1 M.f. C13H11Cl2F4N3O Form Colourless, viscous liquid; (tech., yellow to yellowish-brown liquid). M.p. Pour point 6 °C B.p. Decomp. 240 ºC without boiling V.p. 0.18 mPa (gas saturation method) KOW logP = 3.56 (20 ºC) Henry 3.6 ´ 10-4 Pa m3 mol-1 (20 °C, calc.) S.g./density 1.432 (20 °C) Solubility In water 156 mg/l (pH 7, 20 ºC). Readily soluble in 1,2-dichloroethane, acetone, and methanol. Stability Stable in dilute aqueous solutions at pH 4-9. Stable in water to sunlight.

COMMERCIALISATION
History Fungicide reported by C. Garavaglia et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1, 49). Introduced by Agrimont S.p.A. (now Isagro S.p.A.). Patents EP 234242 Manufacturers Isagro

APPLICATIONS
Biochemistry Sterol C14-demethylase inhibitor. Mode of action Broad-spectrum systemic fungicide with protective, curative and eradicant properties. Absorbed by the roots, stem and leaves, with translocation acropetally to all parts of the plant, including subsequent growth. Uses Control of powdery mildew, brown rust, Septoria and Rhynchosporium on cereals; powdery mildew and scab on pome fruit; powdery mildew on vines and cucumbers; powdery mildew and beet leaf spot on sugar beet; and powdery mildew and rust on vegetables and ornamentals. Applied at 2.5-5 g/hl for fruit and vegetables, 100-125 g/ha for field crops. Formulation types EC; ME; LS; SE. Selected products: 'Domark' (Isagro); 'Eminent' (Isagro); 'Lospel' (Isagro)

OTHER PRODUCTS
'Arpège' (Sipcam Phyteurop); 'Arum' (Bayer CropScience); 'Buongiorno' (Arysta, Isagro); 'Defender' (Sipcam); 'Fief' (Bayer CropScience); 'Greman' (Sipcam Phyteurop); 'Hokuguard' (Arysta, Isagro); 'Juggler' (Sipcam UK); 'Timbal' (Sipcam Phyteurop) mixtures: 'Eminent Star' (+ chlorothalonil) (Isagro); 'Abitre' (+ chlorothalonil) (Bayer CropScience); 'Arbitre' (+ chlorothalonil) (Bayer CropScience); 'Bonanza' (+ prochloraz) (Sipcam Phyteurop); 'Music' (+ chlorothalonil) (Sipcam Phyteurop); 'Timbal F' (+ fentin hydroxide) (Sipcam Phyteurop); 'Voodoo' (+ chlorothalonil) (UK) (Sipcam) Discontinued products mixtures: 'Voodoo' * (+ chlorothalonil) (Monsanto)

ANALYSIS
Product and residue analysis by glc or hplc. Details available from Isagro.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 1248, female rats 1031 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Not irritating to skin; slightly irritating to eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >3.66 mg/l. NOEL In 2 y study, NOAEL for rats 80 mg/kg diet. Other Non-mutagenic. Toxicity class WHO (a.i.) II EC classification R40| Xn; R20/22| N; R51, R53

ECOTOXICOLOGY
Birds Dietary LC50 (5 d) for bobwhite quail 650, mallard ducks 422 mg/kg. Fish LC50 (96 h) for rainbow trout 4.8, bluegill sunfish 4.3 mg/l. Daphnia LC50 (48 h) 3.0 mg/l. Bees LD50 (oral) >130 mg/bee.

ENVIRONMENTAL FATE
Animals Tetraconazole is readily adsorbed, metabolised and excreted with no significant retention in the tissues. The main metabolite identified in urine of rats is 1,2,4-triazole. Plants Extensive metabolism occurs in plants. The identified metabolites are tetraconazole acid, tetraconazole alcohol, triazolylalanine and triazolylacetic acid. Soil/Environment No accumulation in the field. No leaching occurs in standard soils. Koc 531-1922 in 4 soil types.