Fluazinam 氟啶胺

氟啶胺

基本属性
【中文名称】氟啶胺；3-氯-N-（3-氯-5-三氟甲基-2-吡啶基）-α，α，α-三氟-2，6-二硝基-对-甲苯胺
【英文名称】fluazinam;fluaziname;Shirlan;3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-α,α,α-trifluor-2,6-dinitro-p-toluidine;3-chloro-N-(3-chloro-2,6-dinitro-4-(trifluoromethyl) phenyl)-5-(trifluoromethyl)-2-pyridinamine
【结构或分子式】
【相对分子量或原子量】465.1
【密度】1.757g/mL(20℃)
【熔点（℃）】115～117
【蒸气压（Pa）】1.47mPa(25℃)
【毒性LD50(mg/kg)】
雄大、小鼠急性经口LD50＞5000.Ames试验呈阴性。鲤鱼LD50（48h）0.15mg/L。
【性状】
纯品为黄色结晶粉末
【剂型】Shirlan,SC(500g ai/L);フロソサイド,５０％可湿性粉剂和０．５％粉剂
【作用方式】保护性杀菌，且耐雨水冲刷
【使用方法】５０－１００g ai/hm2剂量喷雾，可防治葡萄孢引起的病害；１２５－２５０g ai/hm2土壤处理可防治根肿病，１２．５－２０mg ai/L土壤剂量可防治根霉病。
【溶解情况】
溶解度（g／L）：水 0． 0001（PH5）、0.0017（pH6）、＞1（pH11）、正己烷12、1，2－丙二醇约8.6、环己烷 14、乙酸乙酯 680．甲苯410、丙醇 470、乙醇 470、二氯甲烷330。

用途

本品属2，6-二硝基苯胺类化合物，是保护性杀菌剂。以50～100g(a.i.）/100L剂量可防治由灰葡萄胞引起的病害．本品对交链孢属、葡萄孢属、疫霉属、单轴霉属、核盘菌属和黑垦菌属菌非常有效，对抗苯并咪唑类和二羧酰亚胺类杀茵剂的灰葡萄孢也有良好效果，耐雨水冲刷，持效期长，兼有优良的控制食植性螨类的作用，对十字花科植物根肿病也有卓越的防效，对由根霉菌引起的水稻猝倒病也有很好的防效。防治根肿病的施用剂量为125～250g(a.i.)/ha，防治根霉病的施用剂量为12.5～20mg(a.i.)/ha土壤。

【制备或来源】
4-三氟甲基2,6-二氯苯胺在乙酸中,10℃下用氯气进行氯化，生成4-三氟甲基－2，5，6-三氯苯肢，将后者溶解在乙酸中，室温下与过氧化氢和少量浓硫酸搅拌8小时，生成结晶产物，加入发烟硫酸和硝酸，冰冷却，在100℃加热该混合物，生成2，6-二硝基－4-三氟甲基-5-－氯苯胺。在5℃将上述化合物加到2-氦基-3－氯-5－三氟甲基吡啶、干燥的四氢呋喃和氢氧化钾的混合液中，在室温下搅拌16小时，即得产品。
其他

【其他】
对热、酸、碱稳定，在光照下较易分解。

【生产单位】
日本石原产业公司

fluazinam
Fungicide
FRAC 29, C5

NOMENCLATURE
Common name fluazinam (BSI, draft E-ISO); fluaziname ((m) draft F-ISO)
IUPAC name 3-chloro-N-(3-chloro-5-trifluoromethyl-2-pyridyl)-a,a,a-trifluoro-2,6-dinitro-p-toluidine
Chemical Abstracts name 3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine
CAS RN [79622-59-6] Development codes B-1216; IKF-1216 (Ishihara Sangyo); ICIA0192 (ICI)

PHYSICAL CHEMISTRY
Mol. wt. 465.1 M.f. C13H4Cl2F6N4O4 Form Light yellow crystals. M.p. 115-117 °C V.p. 7.5 mPa (25 °C) KOW logP = 4.1 Henry 4.10 ´ 10-1 Pa m3 mol-1 (calc.) S.g./density 0.366 (25 °C, bulk) Solubility In water 0.135 mg/l (pH 7, 20 °C). In n-hexane 12, acetone 470, toluene 410, diethyl ether 320, dichloromethane 330, ethanol 150 (all in g/l, 20 °C). Stability Stable to acid, alkali and heat. Hydrolysis DT50 42 d (pH 7), 6 d (pH 9), stable at pH 5. Aqueous photolysis DT50 2.5 d. pKa 7.34 (20 °C)

COMMERCIALISATION
History Fungicide discovered and introduced by Ishihara Sangyo Kaisha, Ltd and first marketed in 1990. Manufacturers Ishihara Sangyo

APPLICATIONS
Biochemistry Uncouples mitochondrial oxidative phosphorylation, inhibiting spore germination, hyphal penetration, growth and sporulation. Mode of action Fungicide with protective action. Has little curative or systemic activity, but good residual effect and rain fastness. Uses Control of grey mould and downy mildew on vines; apple scab; southern blight and white mould on peanuts; and Phytophthora infestans and tuber blight on potatoes. Control of clubroot on crucifers, and rhizomania on sugar beet. Applied at 150-750 g/ha. Also for control of mites in apples. Formulation types DP; SC; WP. Selected products: 'Cobbler' (Barclay); 'Frowncide' (Ishihara Sangyo); 'Omega' (ISK Biosciences, Syngenta); 'Shirlan' (Syngenta)

OTHER PRODUCTS
'Altima' (Ishihara Sangyo); 'Legacy' (ISK Biosciences); 'Mapro' (Ishihara Sangyo); 'Sagiterre' (Ishihara Sangyo); 'Sekoya' (Ishihara Sangyo); 'Shogun' (Ishihara Sangyo) mixtures: 'Epok' (+ metalaxyl-M) (Syngenta) Discontinued products: 'Salvo' * (Zeneca)

ANALYSIS
Details from Ishihara Sangyo.

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Irritating to eyes, slightly irritating to skin (rabbits). Tech. is a skin sensitiser, but purified material is not (guinea pigs). Inhalation LC50 for rats 0.463 mg/l.

ECOTOXICOLOGY
Birds Acute oral LD50 for bobwhite quail 1782, mallard ducks 4190 mg/kg. Fish LC50 (96 h) for rainbow trout 0.036 mg/l. Daphnia LC50 (48 h) 0.22 mg/l. Algae EC50 (96 h) for Selenastrum capricornutum 0.16 mg/l. Other a