Myclobutanil 腈菌唑

腈菌唑

简介
通用名：腈菌唑 (Myclobutanil)
分子式：C15H17ClN4
分子量：288.7791
农药类别：杀菌剂
化学分类：唑类作用方式：保护，治疗
化学名称：2-(4-氯苯基)-2-(1H,1,2,4-三唑-1-甲基)己腈
分析方法：气谱法(Rohm&Haas)
理化性质：外观为浅黄色固体，熔点63－68℃(工业品)，沸点202－208mg/L(25℃)，蒸气 压0.213mPa(25℃)，水中溶解度142mg/L(25℃)，溶于一般有机溶剂，酮类、 酯类、醇类和芳香烃类为50－100g/L，不溶于脂肪烃类，一般贮存条件下稳 定， 水溶液暴露于光下分解。毒性：低毒　半衰期：66天

腈菌唑：制剂： EC、SC、WP如25％乳油。

分析方法： GC／HPLC。

作用机理与特点腈菌唑是一类具保护和治疗活性的内吸性三唑类杀菌剂。主要对病原菌的麦角甾醇的生物合成起抑制作用，对子囊菌、担子菌均具有较好的防治效果。该剂持效期长，对作物安全，有一定刺激生长作用。

作用特点
是一类具保护和治疗活性的内吸性三唑类杀菌剂。主要对病原菌的麦角甾醇的生物合成起抑制作用，对子囊菌、担子菌均具有较好的防治效果。该剂持效期长，对作物安全，有一定刺激生长作用。同时对表角甾醇生物合成抑制剂。其具有强内吸性、药效高，对作物安全，持效 期长特点。具有预防和治疗作用。

用途：对白粉病、锈病、黑星病、灰斑病、褐斑病、黑穗病有很好防效。

应用
适宜作物与安全性：苹果、梨、核果、葡萄、葫芦、园艺观赏作物，小麦、大麦、燕麦、棉花和水稻等。对作物安全。
防治对象： 白粉病、黑星病、腐烂病、锈病等。
使用方法： 可用于叶面喷洒和种子处理。使用剂量通常为30～60g（a.l.）／hm2。
防治小麦白粉病每亩每次用25％乳油8～l6g［2～4g（a.i.）／亩］，一般加水75～l00kg，相当于6000～9000倍液，混合均匀后喷雾。于小麦基部第一片叶开始发病即发病初期开始喷雾，共施药两次，两次间隔10～15d。持效期可达20d。还可用拌种方法防治小麦黑穗病、网腥黑穗病等土壤传播的病害，l00kg种子拌药25％乳油25～40ml。
防治梨树、苹果树黑星病、白粉病、褐斑病、灰斑病可用25％乳油6000～10000倍液均匀喷雾，喷液量视树势大小而定。

主要生产企业： 深圳诺普信、青岛浩瀚高科、陶氏益农等

myclobutanil
Fungicide
FRAC 3, G1; DMI: triazole

NOMENCLATURE
Common name myclobutanil (BSI, ANSI, draft E-ISO, (m) draft F-ISO)
IUPAC name 2-p-chlorophenyl-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile; 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
Chemical Abstracts name a-butyl-a-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile
CAS RN [88671-89-0] Development codes RH-3866 (Rohm & Haas)

PHYSICAL CHEMISTRY
Mol. wt. 288.8 M.f. C15H17ClN4 Form Pale yellow solid. M.p. 63-68 ºC (tech.) B.p. 202-208 ºC/1 mmHg V.p. 0.213 mPa (25 ºC) KOW logP = 2.94 (pH 7-8, 25 ºC) Henry 4.33 ´ 10-4 Pa m3 mol-1 (calc.) Solubility In water 142 mg/l (25 ºC). Soluble in common organic solvents, e.g. ketones, esters, alcohols and aromatic hydrocarbons, all 50-100 g/l. Insoluble in aliphatic hydrocarbons. Stability Stable under normal storage conditions. Aqueous solutions decompose on exposure to light, DT50 222 d (sterile water), 0.8 d (sensitised sterile water), 25 d (pond water); no hydrolysis (28 ºC) in 28 d (pH 5, 7, and 9).

COMMERCIALISATION
History Systemic fungicide reported by C. Orpin et al. (Proc. 1986 Br. Crop Prot. Conf. - Pests Dis., 1b, 55) and developed by Rohm & Haas Co. (now Dow AgroSciences). First marketed in 1989. Patents US 4920139 Manufacturers Dow AgroSciences; Sharda; Shenyang

APPLICATIONS
Biochemistry Inhibits ergosterol biosynthesis (steroid demethylation inhibitor). Mode of action Systemic fungicide with protective and curative action. Translocated upwards in the plant. Uses Control of Ascomycetes, Fungi Imperfecti, and Basidiomycetes on a wide variety of crops. The primary use is for powdery mildew (Uncinula necator) control in vines and for combined leaf scab and powdery mildew control in apples. Application rates typically 30-60 g/ha. Also registered for control of Ascomycetes or Basidiomycetes diseases on a broad variety of crops including other pome fruit, stone fruit, cucurbits, strawberries, almonds, tomatoes, vegetables, hops, cotton, cereal seed treatments, turf and ornamentals. It is used as a foliar treatment for control of powdery mildew, shot-hole, blossom blight, anthracnose and rust in stone fruit and nuts; powdery mildew in cucurbits; powdery mildew and rusts on ornamentals; rusts on perennial grasses grown for seed; and as a seed treatment for control of seed- and soil-borne diseases in barley, maize, cotton, rice and wheat; and as a post-harvest treatment in crops such as banana. Formulation types EC; EW; WP; Seed treatment. Selected products: 'Eagle' (Dow AgroSciences); 'Nova' (Dow AgroSciences); 'Rally' (Dow AgroSciences); 'Systhane' (Dow AgroSciences); 'Pudong' (Rocca)

OTHER PRODUCTS
'Laredo' (Dow AgroSciences); 'Nu-Flow M' (Dow AgroSciences); 'Mycloss' (Bayer CropScience, Philagro) mixtures: 'Sabithane' (+ dinocap) (Dow AgroSciences); 'Manhandle' (+ mancozeb) (Lesco) Discontinued products mixtures: 'Ravyl' * (+ ampropylfos+ anthraquinone) (Bayer)

ANALYSIS
Product and residues by gc with FID. Details from Dow AgroSciences.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 65, 67 (see part 2 of the Bibliography). Oral Acute oral LD50 for male rats 1870, female rats 2090 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits >5000 mg/kg. Not a skin irritant; can cause substantial irritation to the eyes (rabbits). Not a skin sensitiser (guinea pigs). Inhalation LC50 for rats 5.1 mg/l. NOEL Dietary NOEL (90 d) for dogs 3.1 mg/kg b.w. daily. Reproductive NOEL for rats 14.7 mg/kg b.w. daily. NOAEL, based on chronic feeding, oncogenicity and reproductive studies 2.5 mg/kg b.w. daily. ADI (JMPR) 0.03 mg/kg b.w. [1992]. Other Non-teratogenic in rats and rabbits, and various mutagenicity tests proved negative. Not mutagenic in the Ames assay. Toxicity class WHO (a.i.) III EC classification R63| Xn; R22| Xi; R36| N; R51, R53

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 510, grey partridges 1635 mg/kg. Dietary LC50 (8 d) for bobwhite quail and mallard ducks > 5000 mg/kg. Fish LC50 (96 h) for bluegill sunfish 2.4, rainbow trout 2.0 mg/l. Daphnia LC50 (48 h) 11 mg/l. Algae EC50 (96 h) for Scenedesmus subspicatus 2.4 mg/l. Bees Non-toxic to bees. LD50 (oral) 171 mg/bee; (contact) 200 mg/bee. Worms Acute LC50 for Eisenia foetida 99 mg/kg; reproduction NOEC for Eisenia foetida >10.3 mg/kg.

ENVIRONMENTAL FATE
Animals In animals, undergoes oxidation at the butyl group to a ketone and an alcohol, with partial conjugation to a glucoside. Following oral administration, rapidly excreted in the faeces and urine. Plants In plants, metabolism is the same as in animals. Soil/Environment In soil, DT50 66 d (silt loam). Decomposition is through highly polar triazole compounds, with further degradation by ring splitting. No degradation under anaerobic conditions. Stable to hydrolysis, but decomposes in aqueous solutions upon exposure to light; DT50 in pond water typically 15-25 days. Low mobility in soil; Koc 224-937 ml/g.