Ofurace 甲呋酰胺

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CAS编码: 58810-48-3
IUPAC名称: (±)-α-(2-chloro-N-2,6-xylylacetamido)-γ-butyrolactone
英文通用名称: Ofurace
中文通用名称: 呋酰胺
英文商品名称: Acetamide; Milfuram; Ortho 20615; RE 20615
中文商品名称: 甲呋酰胺
英文化学名称: (±)-2-chloro-N-(2,6-dimethylphenyl)-N-(tetrahydro-2-oxo-3-furanyl)acetamide
中文化学名称: (±)-α-2-氯-N-2,6-二甲苯基乙酰氨基-γ-丁内酯
分子式: C14H16ClNO3
分子量: 281.7
原药为无色晶体,熔点145~146℃,密度1.366,20℃蒸汽压-2 mPa (20 ℃)
剂型:WP (500g.ai/kg) 。
作用方式: 内吸性杀菌, 具有双向传导功能。
防治对象: 对藻菌纲植物病原菌有特效,如葡萄上的单轴霉菌(葡萄霜霉病菌)、马铃薯上的疫霉菌(马铃薯晚疫病菌)和油菜上的霜霉菌(十字花科霜霉病菌)。可用来防治番茄晚疫病、马铃薯晚疫病、葡萄霜霉病、烟草霜霉病、 向日葵霜霉病等。


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FRAC 4, A1; phenylamide: butyrolactone


Common name ofurace (BSI, draft E-ISO, (m) draft F-ISO, ANSI)
IUPAC name (?-a-(2-chloro-N-2,6-xylylacetamido)-g-butyrolactone
Chemical Abstracts name (?-2-chloro-N-(2,6-dimethylphenyl)-N-(tetrahydro-2-oxo-3-furanyl)acetamide
CAS RN [58810-48-3] unstated stereochemistry EEC no. 261-451-9 Development codes RE 20615 (Chevron); AE F057623 (AgrEvo)

Composition Tech. grade is ³97% pure. Mol. wt. 281.7 M.f. C14H16ClNO3 Form Colourless crystals; (tech. is an off-white to light beige, crystalline powder). M.p. 145-146 ºC V.p. 2 ´ 10-2 mPa (20 ºC) KOW logP = 1.39 (20 °C) Henry 3.9 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.43 (20 ºC) Solubility In water 146 mg/l (20 °C). In acetone 60-75, 1,2-dichloroethane 300-600, ethyl acetate 25-30, methanol 25-30, p-xylene 8.6, heptane 0.0322 (all in g/l). Stability Hydrolysis is rapid in alkali, DT50 7 h (pH 9, 35 °C), but stable in acidic media and at elevated temperatures. Photochemical degradation in water, DT50 7 d.

History Systemic fungicide introduced by Chevron Chemical Co. Rights transferred to Schering AG (now Bayer CropScience) in 1992.

Biochemistry It is assumed that it inhibits protein synthesis in fungi, by interference with the synthesis of ribosomal RNA. Mode of action Systemic fungicide with curative and protective action. Absorbed rapidly by the foliage and roots, with translocation both acropetally and basipetally. Acts by inhibiting spore germination or blocking mycelium formation. Uses In combination with other fungicides, for control of Phycomycetes, particularly downy mildew of vines, and late blights of potatoes and tomatoes. Formulation types SC; WP.

'Caltan P' (Bayer CropScience); 'Polyplus' (Bayer CropScience); 'Vamin' (Bayer CropScience) mixtures: 'Patafol' (+ mancozeb) (Bayer CropScience)

Product analysis by hplc. Residues determined by glc.

Oral Acute oral LD50 for male rats 3500, female rats 2600, mice >5000, rabbits >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Moderate eye irritant; mild skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 for rats 2060 mg/m3. NOEL Long-term NOEL for rats 2.5 mg/kg b.w. daily. ADI 0.03 mg/kg b.w. Other Not mutagenic, not teratogenic, not carcinogenic. Toxicity class WHO (a.i.) U; EPA (formulation) III

Birds Acute oral LD50 for red-legged partridge >5000 mg/kg. Fish LC50 (96 h) for rainbow trout 29, golden orfe 57 mg/l. Daphnia EC50 (48 h) 46 mg/l. Bees Non-toxic to bees; LD50 (oral) >58 mg/bee.

Animals Ofurace is rapidly excreted, undergoing extensive phase I and phase II biotransformation. Plants Similar metabolic pathways have been detected in vines, tomatoes, and potatoes. Ofurace is relatively stable on the plant surface, but, once it has penetrated into plant material, it is metabolised by hydroxylation and conjugation. Ofurace has been defined as the residue to be monitored. Soil/Environment Degraded in soil, field DT50 c. 26 d. Only moderately adsorbed to soil and is considered to be moderately mobile. Undergoes photochemical degradation in water and is degraded in water sediment systems.