Fenamidone 咪唑菌酮

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中文通用名称: 咪唑菌酮
英文通用名称: fenamidone
化学名称: (S)-5-methyl-2-methylthio-5-phenyl-3-phenylamino-3,5-dihydroimidazol-4-one
(S)- 3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imida-

化学结构类型: 咪唑啉酮类
理化性质: 白色粉状固体,熔点为137℃,密度为1.285,蒸气压3.4 × 10-7Pa (25℃) ,水中溶解度 (20℃) :7.8mg/l。
毒性: 大鼠急性经口L D50:雄>5000mg/kg,雌2028mg/kg; 大鼠急性经皮L D50 (24小时):>2000mg/kg;本品对兔眼睛和皮肤无刺激。Ames试验、微核试验为阴性。
制剂: SC
作用机理: 线粒体呼吸抑制剂。具有触杀、渗透、内吸活性,具有良好的保护和治疗活性。
适宜作物及对作物的安全性: 葡萄、马铃薯、番茄、烟草、蔬菜、向日葵、豆类等。在推荐剂量下,对作物安全。
防治对象: 由卵菌纲病原菌引起的霜霉病、疫病 (包括早疫病和晚疫病) 等,对果树黑斑病亦有很好的活性。
应用: 本品主要用于叶面处理,使用剂量为75~150克有效成分/公顷,同乙磷铝一起使用具有增效作用。

主要原料与中间体: 苯乙酮、二硫化碳、苯肼
分析方法: GC/HPLC
开发公司: 安万特公司


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FRAC 11, C3; strobilurin type: imidazolinone


Common name fenamidone (BSI, pa ISO (not Japan))
IUPAC name (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one
Chemical Abstracts name (S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one
CAS RN [161326-34-7] Development codes RPA 407213 ((S)- enantiomer, Rhône-Poulenc)

Mol. wt. 311.4 M.f. C17H17N3OS Form White woolly powder, with no characteristic odour. M.p. 137 °C V.p. 3.4 ´ 10-4 mPa (25 °C) KOW logP = 2.8 (20 °C) S.g./density 1.285 Solubility In water 7.8 mg/l (20 °C). In acetone 250, acetonitrile 86.1, dichloromethane 330, methanol 43, n-octanol 9.7 (mg/l, 20 °C). Stability Hydrolysis DT50 (sterile conditions) 41.7 d (pH 4), 411 d (pH 7), 27.6 d (pH 9); phototransformation DT50 5 d. Other properties Surface tension 72.9 mN m-1 (20 °C).

History Reported by R. T. Mercer et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 319). Discovered by Rhône-Poulenc Agro and developed by Aventis; now owned and distributed by Bayer CropScience. First registration and launch in 2001. Manufacturers Bayer CropScience

Biochemistry Inhibits mitochondrial respiration by blocking electron transport at ubihydroquinone: cytochrome c oxidoreductase. Mode of action Protectant and curative fungicide with antisporulant and trans-laminar systemic activity. Uses Foliar fungicide with activity against Oomycete fungi, such as grape and vegetable downy mildew including Bremia, Peronospora, Plasmopara, Pseudoperonospora spp. and diseases caused by Phytophthora infestans (at 75-150 g/ha). It can also be used as a seed treatment or soil drench to control Pythium spp. It also suppresses other pathogens, including Alternaria spp., as well as certain leaf spot diseases, powdery mildews and rusts. Formulation types SC; WG (for mixtures). Selected products: 'Censor' (Bayer CropScience); 'Reason' (Bayer CropScience)

Mixtures: 'Elicio' (+ fosetyl-aluminium) (Bayer CropScience); 'Mildex' (+ fosetyl-aluminium) (Bayer CropScience); 'Noblite' (+ mancozeb) (Bayer CropScience); 'Oracle' (+ copper hydroxide) (Bayer CropScience); 'Sagaie' (+ mancozeb) (Bayer CropScience); 'Secure' (+ mancozeb) (Bayer CropScience); 'Sereno' (+ mancozeb) (Bayer CropScience); 'Sonata' (+ mancozeb) (Bayer CropScience); 'Tertio' (+ fosetyl-aluminium+ cymoxanil) (Bayer CropScience); 'Utilis' (+ copper hydroxide) (Bayer CropScience); 'Verita' (+ fosetyl-aluminium) (Bayer CropScience)

Pure active substance by hplc. Methods for the determination of residues are available upon request from Bayer CropScience.

Oral Acute oral LD50 for female rats 2028, male rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to skin and eyes (rabbits); not a skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats 2.1 mg/l air. NOEL (90 d) for rats 32.5 mg/kg/day; (52 w) for dogs 100 mg/kg/day. ADI 0.028 mg/kg. Other Negative in Ames and micronucleus tests. Not teratogenic in rats and rabbits; no reproductive, developmental or carcinogenic effects.

Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail and mallard ducks >5200 mg/kg. Fish LC50 (96 h) for rainbow trout and bluegill sunfish 0.74 mg/l. Algae EbC50 (72 h) 3.84 mg/l; ErC50 (72 h) 12.29 mg/l. Other aquatic spp. NOEC for Chironomus riparius 0.05 mg/l. Bees LD50 (96 h, oral) >159.8 mg/bee; LD50 (96 h, contact) 74.8 mg/bee. Worms LC50 (14 d) for Eisenia foetida 25 mg/kg.

Animals At low doses (3 mg/kg) in mammals, fenamidone was relatively well absorbed in both sexes and intensively metabolised by phase I reactions (oxidation, reduction and hydrolysis) and phase II reactions (conjugation); the majority of the administered dose was relatively rapidly excreted via the biliary route. At high doses, absorbtion was low: 50-60% of the parent compound was found in faeces. Plants The pattern of metabolite formation is similar in all crops; fenamidone forms the largest part of the residue and the only significant metabolite is RPA 405862, formed by hydrolysis of the thio-methyl side chain. Soil/Environment Hydrolysis (see Stability) follows pseudo first-order reaction kinetics, resulting in three hydrolysis products that exceed 10% of applied radioactivity. Fenamidone is readily photodegraded in aqueous conditions. The active compound is considered to be not readily biodegradable, non-volatile and therefore not found in air.