Fenbuconazole 腈苯唑

腈苯唑

CAS编码： 114369-43-6
Development Codes： RH-7592;
IUPAC名称： 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile
英文通用名称： Fenbuconazole
中文通用名称： 腈苯唑
英文商品名称： Indar[罗姆-哈斯]; RH-7592
中文商品名称： 苯氰唑; 应得[罗姆-哈斯]; 唑菌腈;分菌氰唑
英文化学名称： α-[2-(4-chlorophenyl)ethyl]-α-phenyl-1H-1,2,4-triazole-1-propanenitrile
中文化学名称： 4-(4-氯苯基)-2-苯基-2(1H-1,2,4-三唑-1-yl甲基)丁腈

理 化 性 质：
分子式： C19H17ClN4
分子量： 336.8
性状描述： 无色结晶，熔点124－126℃，蒸气压0.005mpa(20℃)，水中溶解度0.2mg/L (25℃)。能溶于大多数有机溶剂，如:丙酮、乙醚、乙醇和芳香烃中。不溶于 脂肪烃中。300℃下稳定。 在黑暗中稳定。

制剂： EC、EW、WP、SC。
作用机理与特点： 甾醇脱甲基化抑制剂，内吸传导型杀菌剂，能抑制病原菌菌丝的伸长，阻止已发芽的病菌孢子侵入作物组织。在病菌潜伏期使用，能阻止病菌的发育，在发病后使用，能使下一代孢子变形，失去继续传染能力，对病害既有顸防作用又有治疗作用。
应用：
适宜作物与安全性：禾谷类作物、水稻、甜菜、葡萄、香蕉、果树如桃、苹果等。
防治对象： 腈苯唑对禾谷类作物的壳针孢属、柄锈菌属和黑麦喙孢，甜菜上的甜菜生尾孢，葡萄上的葡萄孢属、葡萄球座菌和葡萄钩丝壳，核果上的丛梗孢属，果树上如苹果黑星菌等以及对大田作物、水稻、香蕉、蔬菜和园艺作物的许多病害均有效；还有香蕉叶斑病等。
使用方法：
腈苯唑既可作叶面，也可作种子处理剂。防治禾谷类作物病害使用剂量为75～125g（a.i.）／hm2，防治油莱病害使用剂量为60～75g（a.i.）／hm2，防治甜菜病害使用剂量为65～280g（a.i.）／hm2，防治花生病害使用剂量为75～150g（a.i.）／hm2，防治水稻病害使用剂量为50～150g（a.i.）／hm2，防治葡萄病害使用剂量为30～45g（a.i.）／hm2，防治果树病害使用剂量为50～75g（a.i.）／hm2，防治蔬菜病害使用剂量为50～l00g（a.i.）／hm2，防治草坪病害使用剂量为75～250g（a.i.）／hm2。
应用：防治香蕉叶斑病在香蕉下部叶片出现叶斑之前或刚出现叶斑，用24％乳油400倍液，每隔7～14d喷雾1次，连续使用多次（但不要超过4次），对香蕉叶面有良好的保护作用。在台风雨季来临或叶斑出现时，用24％乳油l000倍液或每l00L水加24％乳油l00ml，每隔7～14d喷雾1次，连续用2～3次对香蕉叶斑病有良好的治疗作用。
防治桃树褐腐病在桃树发病前或发病始期喷药，用24％乳油2500-3000倍液或每l00L水加24％乳油33.3～40mI喷雾。

fenbuconazole
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name fenbuconazole (BSI, draft E-ISO, ANSI)
IUPAC name 4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazol-1-ylmethyl)butyronitrile
Chemical Abstracts name a-[2-(4-chlorophenyl)ethyl]-a-phenyl-1H-1,2,4-triazole-1-propanenitrile
CAS RN [114369-43-6] unstated stereochemistry Development codes RH-7592; RH-57592 (both Rohm & Haas)

PHYSICAL CHEMISTRY
Mol. wt. 336.8 M.f. C19H17ClN4 Form Off-white solid with a faint sulfur-like odour. M.p. 126.5-127 °C B.p. unstable above 300 °C V.p. 3.4 ´ 10-1 mPa (25 °C, vapour pressure balance) KOW logP = 3.23 (25 °C) Henry 3.01 ´ 10-5 Pa m3 mol-1 (calc.) S.g./density 1.27 (20 °C) Solubility In water 3.8 mg/l (25 °C). In acetone and 1,2-dichloroethane >250, ethyl acetate 132, methanol 60.9, octanol 8.43, xylene 26.0, n-heptane 0.0677 (all in g/l, 20 °C). Stability Stable to hydrolysis in the dark, DT50 >2210 d (pH 5), 3740 d (pH 7), 1370 d (pH 9). Thermostable up to 300 ºC.

COMMERCIALISATION
History Fungicide reported by D. Briant et al. (Proc. 1988 Br. Crop Prot. Conf. - Pests Dis., 1, 33). Introduced by Rohm & Haas Co. (now Dow AgroSciences) in 1992. Patents US 5087635 Manufacturers Dow AgroSciences

APPLICATIONS
Biochemistry Steroid demethylation inhibitor. Mode of action Penetrant fungicide with residual protectant activity and low translocation in the plant. Uses Initial registration was obtained for control of Septoria species and rusts on cereals (at 75 g/ha). Subsequent registrations have been obtained in Europe for use in vines for control of powdery mildew (Uncinula necator) and black rot (Guignardia bidwellii), in stone fruit for control of powdery mildew and Monilinia spp., and in pome fruit for control of apple scab and powdery mildew (at 30-50 g/ha). In North America, product registration for use on pecans and stone fruit was obtained in 1995. Further global markets include a wide range of diseases on fruits, tree nuts, citrus, bananas, rice and vegetables. Formulation types EC; EW; OD; SC. Selected products: 'Enable' (Dow AgroSciences); 'Indar' (Dow AgroSciences)

OTHER PRODUCTS
'Kruga 5EC' (Interfarm); 'Kruga' (Headland); 'Reward' (Interfarm); 'Surpass 5' (Interfarm) mixtures: 'Karamat' (+ dinocap) (Dow AgroSciences); 'Graphic' (+ propiconazole) (Syngenta); 'Mirage Extra' (+ prochloraz) (PBI, Makhteshim-Agan); 'Myriad' (+ fenpropimorph) (Bayer CropScience); 'Nordika' (+ prochloraz) (Bayer CropScience, BASF); 'Troika' (+ carbendazim) (Bayer CropScience) Discontinued products: 'Reward' * (Headland); 'Surpass' * (Headland); 'Tenere' * (Ciba) mixtures: 'Unison' * (+ tridemorph) (PBI)

ANALYSIS
Product analysis by gc. Details from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 80, 82 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats 2000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Non-irritating to eyes and skin (tech.); severe irritant to eyes and skin (EC formulation) (rabbits). No dermal sensitisation (Buehler test). Inhalation LC50 (4 h) for rats >2.1 mg/l air (for tech.). NOEL NOEL for reproductive effects 6.3 mg/kg b.w. daily; NOEL for developmental effects 30 mg/kg b.w. daily. No adverse reproductive or foetal effects have been observed at rates below a maternally toxic dose. NOAEL based on results of chronic feeding, oncogenicity and reproductive studies 3 mg/kg b.w. daily. ADI (JMPR) 0.03 mg/kg b.w. [1997]. Other Non-mutagenic in a variety of tests. Toxicity class EPA (formulation) II, (tech., III)

ECOTOXICOLOGY
Birds Dietary LC50 (8 d) for bobwhite quail 4050, mallard ducks 2110 mg/kg diet. LC50 (21 d) for bobwhite quail 2150 mg/kg daily. Fish LC50 (96 h) for bluegill sunfish 1.68 mg/l (tech.), for rainbow trout 1.5 mg/l. Chronic NOEC for rainbow trout 0.33 mg/l. Daphnia Acute EC50 2.2 mg/l; chronic NOEC 0.078 mg/l. Algae EC50 (5 d) for Selenastrum capricornutum 0.47 mg/l. Other aquatic spp. Chronic NOEC to sediment dweller (Chironomus riparius) 1.73 mg/l. Bees LC50 (96 h, dust exposure) >0.29 mg/bee. Worms LC50 (14 d) for Eisenia foetida 98 mg/kg soil. Other beneficial spp. Harmless in laboratory studies on Poecilus cupreus, Chrysoperla carnea, Coccinella septempunctata, and Typhlodromus pyri (IOBC).

ENVIRONMENTAL FATE
Plants In peanuts, degraded by three routes: oxidation at the benzylic carbon, leading to oxidative degradation products including a ketone and some lactones, substitution on the carbon next to the triazole ring, leading to triazolylalanine and triazolylacetic acid (presumably via free triazole), and hydroxylation followed by conjugation at the 3- position of the chlorophenyl ring. Soil/Environment Soil adsorption Koc 2100-9000 (clay, loam, sand, sandy loam, silty clay loam).