Epoxiconazole 氟环唑

中文通用名称: 氟环唑
英文通用名称: epoxiconazole （ISO建议名）
商品名称: Opus, 欧霸
试验代号: BAS 480F
化学名称:
(2RS,3RS)-1-[3-(2-氯苯基)-2,3-环氧-2-(4-氟苯基)丙基]-1氢-1,2,4-三唑
(2RS,3RS)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
CA主题索引名及CAS登录号:
cis-1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole
[106325-08-0]

化学结构类型: 三唑类

理化性质: 纯品为无色结晶体；熔点136.2℃；密度1.384(25℃)；蒸气压<1.0×10-5Pa(25℃)；分配系数(PH =7)LogP=3.1；溶解度(20℃,mg/l)水6.63，丙酮14.4，二氯甲烷29.1；稳定性 在p H 7和p H 9条件下12天不水解。

毒性: 大鼠急性经口L D50：>5000mg/kg；大鼠急性经皮LD50：>2000mg/kg；大鼠吸入LC50(4小时)：>5.3mg/l空气；本品对兔眼睛和皮肤无刺激。鹌鹑急性经口LD50：>2000mg/kg；鹌鹑LC50：5000mg/kg。 鱼LC50(96小时,mg/l)：鳟2.2~2.4，大翻车鱼4.6~6.8；水蚤LC50(48小时)：8.7mg/l。

制剂: SC、 SE
作用机理: 甾醇生物合成中C-14脱甲基化酶抑制剂，兼具保护和治疗作用。
适宜作物: 禾谷类作物、糖用甜菜、花生、油菜、草坪、咖啡、水稻及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: 立枯病、白粉病、眼纹病等十多种病害

使用方法:
BAS 480F是广谱杀菌剂。田间试验结果显示其对一系列禾谷类作物病害如立枯病、白粉病、眼纹病等十多种病害有很好的防治作用，并能防治糖用甜菜、花生、油菜、草坪、咖啡、水稻及果树等中的病害。其不仅具有很好的保护、治疗和铲除活性，而且具有内吸和较佳的残留活性，使用剂量通常为75~125克有效成分/公顷。喷雾处理。
合成方法:
以邻氯甲苯、氟苯为起始原料，经如下反应制得目的物：

主要原料与中间体: 邻氯甲苯、氟苯、三苯基磷、三唑
分析方法: G C或HPLC
开发公司: 巴斯夫公司。
专利申请: EP 0094564；US4464381
在我国登记情况: 在我国已登记。且已得到中国中国石油和化学工业局授予行政保护，授权号：NB－GE96061006。

epoxiconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name epoxiconazole (BSI, pa ISO)
IUPAC name (2RS,3SR)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole
Chemical Abstracts name cis-1-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole
CAS RN [106325-08-0] EEC no. 406-850-2 Development codes BAS 480F (BASF)

PHYSICAL CHEMISTRY
Composition Material is the 2R,3S- 2S,3R- enantiomer pair. Mol. wt. 329.8 M.f. C17H13ClFN3O Form Colourless crystals. M.p. 136.2 ºC V.p. <0.01 mPa (20 ºC) KOW logP = 3.44 (pH 7) Henry <4.71 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.384 (room temperature) Solubility In water 6.63 ´ 10-4 g/100 ml (20 ºC). In acetone 14.4, dichloromethane 29.1, heptane 0.04 (all in g/100 ml). Stability No hydrolysis at pH 5 and pH 7 within 12 days.

COMMERCIALISATION
History Developed and introduced by BASF AG; first registrations in 1993. Patents EP 94564; US 4464381 Manufacturers BASF

APPLICATIONS
Biochemistry Inhibition of C-14-demethylase in sterol biosynthesis. Mode of action Preventive and curative fungicide. Uses Broad-spectrum fungicide, with preventive and curative action, for control of diseases caused by Ascomycetes, Basidiomycetes, and Deuteromycetes in cereals, sugar beet, peanuts, oilseed rape, and ornamentals, generally at 125 g/ha. Formulation types SC; SE. Compatibility Compatible with morpholines and MBC-derivatives. Selected products: 'Opus' (BASF); 'Soprano' (Makhteshim-Agan); mixtures: 'Allegro' (+ kresoxim-methyl) (BASF); 'Opus Team' (+ fenpropimorph) (BASF)

OTHER PRODUCTS
'Swing' (BASF) mixtures: 'Duett' (+ carbendazim) (BASF); 'Eclipse' (+ fenpropimorph) (BASF); 'Juwel' (+ kresoxim-methyl) (BASF); 'Landmark' (+ kresoxim-methyl) (BASF); 'Mantra' (+ fenpropimorph+ kresoxim-methyl) (BASF); 'Ogam' (+ kresoxim-methyl) (BASF); 'Opera' (+ pyraclostrobin) (BASF); 'Opponent' (+ kresoxim-methyl+ pyraclostrobin) (BASF); 'Opus Forte' (+ tridemorph) (BASF); 'Opus Plus' (+ tridemorph) (BASF); 'Rex' (+ thiophanate-methyl) (BASF); 'Swing Gold' (+ dimoxystrobin) (BASF); 'Tango Duo' (+ tridemorph) (BASF); 'Avalon' (+ kresoxim-methyl) (Barclay); 'Capricorn' (+ carbendazim) (Bayer CropScience); 'Epoxifen' (+ fenpropimorph) (Standon); 'Galore' (+ fenpropimorph) (GreenCrop); 'KME' (+ kresoxim-methyl) (Me2); 'Landgold Strobilurin KE' (+ kresoxim-methyl) (Landgold); 'Riverdance' (+ fenpropimorph) (Barclay); 'Soprano C' (+ carbendazim) (Makhteshim-Agan) Discontinued products: 'Epic' * (BASF)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Non-irritating to eyes and skin of rabbits. Inhalation LC50 (4 h) for rats >5.3 mg/l air. NOEL (carcinogenicity) for mice 0.81 mg/kg b.w. ADI 0.0032 mg/kg. EC classification R40| R61| R62| N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for quail >2000 mg/kg. LC50 for quail 5000 mg/kg. Fish LC50 (96 h) for trout 2.2-4.6, bluegill sunfish 4.6-6.8 mg/kg. Daphnia LC50 (48 h) 8.7 mg/l. Algae EC50 (72 h) for green algae 2.3 mg/l. Bees LD50 >100 mg/bee. Worms EC50 (14 d) >1000 mg/kg soil.

ENVIRONMENTAL FATE
Animals A.i. is readily excreted via faeces. There are no major metabolites, but a high number of minor metabolites was identified. The important metabolic reactions were cleavage of the oxirane ring, hydroxylation of the phenyl rings and conjugation. Plants There is extensive degradation. Soil/Environment Degradation in soil is by microbial activity, DT50 c. 2-3 mo. Koc 957-2647.