Hexaconazole 己唑醇

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己唑醇

英文通用名:hexaconazole
分子式:C14H17Cl2N3O
分子式:314.02
化学名:(RS)-2-(2,4-二氯苯基)-1-(1H-1,2,4-三唑-1-基)-己-2-醇
CA登记号:[79983-71-4]
结构式: 已唑醇 结构式

性状
外观:米黄色疏松粉末;比重或密度:约1.04(20℃);熔点:110-112℃;蒸汽压:0.018mPa(20℃);熔解度:水中0.018mg/L,甲醇246g/L,丙酮164g/L,甲苯59g/L,己烷0.8g/L
纯品为无色晶体,熔点111°C,蒸气压0.11mPa(20°C) 25°C,密度1.29g/cm3。溶解性(20°C),水0.018mg/L,甲醇246g/L,甲苯59g/L,稳定性,室温(40°C以下)至少9个月内不分解,酸、碱性(PH5、7-9)水溶液中30天内稳定。PH7水溶液中紫外线照射下10天内稳定。

作用机理
作用机理:属唑类杀菌剂,甾醇脱甲基化抑制剂,对真菌尤其是担子菌门和子囊菌门引起的病害有广谱性的保护和治疗作用。破坏和阻止病菌的细胞膜重要组成成分麦角甾醇的生物合成,导致细胞膜不能形成,使病菌死亡。具有内吸、保护和治疗活性。

防治对象
防治对象:有效地防治子囊菌、担子菌和半知菌所致病害,尤其是对担子菌纲和子囊菌纲引起的病害如白粉病、锈病、黑星病、褐斑病、炭疽病等有优异的保护和铲除作用。对水稻纹枯病有良好防效。
适宜作物与安全性果树如苹果、葡萄、香蕉,蔬菜(瓜果、辣椒等),花生,咖啡,禾谷类作物和观赏植物等。在推荐剂量下使用,对环境、作物安全,但有时对某些苹果品种有药害。

使用方法
使用方法:茎叶喷雾,使用剂量通常为15~250g(a.i.)/hm2。以10~20mg/L喷雾,能有效地防治苹果白粉病,苹果黑星病,葡萄白粉病;以20~50mg(a.i.)/L喷雾,可有效防治咖啡锈病或以30g(a.i.)/hm2防治咖啡锈病,效果优于三唑酮[250g(a.i.)/hm2];以20-50g(a.i.)/hm2可防治花生褐斑病;以15~20mg(a.i.)/L可防治葡萄白粉病和黑腐病。

 

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hexaconazole
Fungicide
FRAC 3, G1; DMI: triazole

  Hexaconazole

NOMENCLATURE
Common name hexaconazole (BSI, ANSI, draft E-ISO, (m) draft F-ISO)
IUPAC name (RS)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol
Chemical Abstracts name (?-a-butyl-a-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-ethanol
CAS RN [79983-71-4] Development codes PP523; ICIA0523 (both ICI)

PHYSICAL CHEMISTRY
Composition Tech. is >85% pure. Mol. wt. 314.2 M.f. C14H17Cl2N3O Form White, crystalline solid. M.p. 110-112 ºC V.p. 0.018 mPa (20 ºC) KOW logP = 3.9 (20 ºC) Henry 3.33 ´ 10-4 Pa m3 mol-1 (calc.) S.g./density 1.29 g/cm3 (25 ºC) Solubility In water 0.017 g/l (20 ºC). In dichloromethane 336, methanol 246, acetone 164, ethyl acetate 120, toluene 59, hexane 0.8 (all in g/l, 20 ºC). Stability Stable for at least 6 years at ambient temperatures. Stable to hydrolysis and photolysis in water. Formulations stable in sales containers for 6 months at 50 ºC, and 2 years at ambient temperature.

COMMERCIALISATION
History Fungicide introduced by ICI Agrochemicals (now Syngenta AG) and first marketed in 1986. Manufacturers Rallis; Sannong; Sharda; Syngenta

APPLICATIONS
Biochemistry Inhibits ergosterol biosynthesis (steroid demethylation inhibitor). Mode of action Systemic fungicide with protective and curative action. Uses Control of many fungi, particularly Ascomycetes and Basidiomycetes, e.g. Podosphaera leucotricha and Venturia inaequalis on apples, Guignardia bidwellii and Uncinula necator on vines, Hemileia vastatrix on coffee, and Cercospora spp. on peanuts, at 15-250 g/ha. Also used on bananas, cucurbits, peppers and other crops. Phytotoxicity Non-phytotoxic when used as directed. Some injury noted on McIntosh apples. Formulation types OL; SC; SG. Selected products: 'Anvil' (fruit) (Syngenta); 'Planete' (cereals) (Syngenta); 'Canvil' (Vapco); 'Contaf' (Rallis); 'Elexa' (Cequisa); 'Force' (Devidayal); mixtures: 'Columbia' (+ fenpropidin) (Syngenta)

OTHER PRODUCTS
'Proseed' (Syngenta); 'Blin' (IQV); 'Hexol' (Excel) mixtures: 'Acanto Dos' (+ picoxystrobin) (cereals) (Syngenta); 'Amistar Ter' (+ azoxystrobin) (cereals, peas) (Syngenta); 'Lynx' (+ chlorothalonil) (Syngenta); 'Sirius' (+ chlorothalonil) (Syngenta); 'Oscar' (+ bupirimate) (Makhteshim-Agan) Discontinued products: 'Bullet 5' * (Agro Chemicals) mixtures: 'Halley' * (+ ethirimol) (Zeneca)

ANALYSIS
Product by glc and FID. Residues by glc with either NPD, thermionic or ECD detection. See K. J. Harradine et al., in Comp. Anal. Profiles, Chapt. 2.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 59, 61 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 2189, female rats 6071 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Mild irritant to eyes; non-irritating to skin (rabbits). Moderate skin sensitiser (guinea pigs). Inhalation LC50 (4 h) for rats >5.9 mg/l. NOEL NOAEL (2 y) for rats 10 mg/kg diet; NOAEL (2 y) for mice 40 mg/kg diet. ADI (JMPR) 0.005 mg/kg b.w. [1990]. Other Non-mutagenic. Toxicity class WHO (a.i.) U; EPA (formulation) IV EC classification Xn; R22| R43| N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for mallard ducks >4000 mg/kg. Fish LC50 (96 h) for rainbow trout 3.4, mirror carp 5.94, sheepshead minnow 5.4 mg/l. Daphnia LC50 (48 h) 2.9 mg/l. Bees Acute oral and contact LD50 for honeybees >0.1 mg/bee. Worms LC50 (14 d) 414 mg/kg.

ENVIRONMENTAL FATE
Animals Readily excreted by mammals, with no significant retention in organs or tissues. Plants For details of the metabolism of hexaconazole in cereals, see M. W. Skidmore et al., Br. Crop Prot. Conf. - Pests Dis., 1990, 3, 1035-1040. Soil/Environment Rapidly degraded in soils in laboratory tests.