Fentin acetate 三苯基醋酸锡 薯瘟锡

三苯基醋酸锡

简介
薯瘟锡，化学名称为三苯基醋酸锡
分子量： 409
分子式：C20H18O2Sn
英文名称为： fentin acetate
化学名称： triphenyltin acetate

化学性质
白色无味结晶粉末，熔点118-122℃。水中溶解度为28ppm（20℃）， 微溶于大多数有机溶剂。工业品纯度为90%左右，置于干燥处贮存是稳定的，当暴露于空气和阳光下较易分解。最后形成不溶性锡化合物，能与一般农药混用，但不能与油乳剂混用。

毒性：
白鼠急性口服LD50 为125 mg/kg
白鼠急性经皮LD50 为500 mg/kg
对蜜蜂无害。薯瘟锡对植物药害极小，在紫外线作用下很快分解为元素锡。 例如：其水溶液在1小时内分解率达90%，在动物体内代谢途径是二苯基锡、一苯基锡，最后分解为对人体无毒的元素锡。
每天喂牛3.2克，持续46天，可以观察到大部分锡化合物随粪便排出体外，两周后其牛奶中含水量痕迹量，八周后已基本排泄完毕。在鼠体中也得到相似的实验结果。

应用范围
大田一般用量 20-40克/亩。
（1） 防治甜菜褐斑病，提高产糖量60-80%。
（2） 防治马铃薯晚疫病，可提高产量度20%。
（3） 防治大豆炭疽病、黑点病、褐纹病、紫斑病与多菌灵一起混用，药效很好。
（4） 对水稻稻瘟病、稻曲病、条斑病也有较好防效，优于富士一号。
（5） 对洋葱黑斑病、芹菜叶枯病、菜豆炭疽病、咖啡的生尾孢病也都有很好的防效。
（6） 特别对福寿螺、藻类、水蜗牛有着特殊防效，优于百螺杀一类药剂。

供应商名目
招远市宏信化工有限公司[1]
上海美格国际贸易有限公司
常州市丰登农药厂
上海明太化工发展有限责任公司

fentin
Fungicide
FRAC 30, C6; organotin fungicide

NOMENCLATURE
fentin
Common name fentin (BSI, E-ISO); fentine ((f) F-ISO); fenolovo* (former exception, USSR); chemical name is used (Republic of South Africa, USA)
IUPAC name triphenyltin
Chemical Abstracts name triphenylstannylium
CAS RN [668-34-8] Development codes VP 1940; Hoe 02824 (Hoechst)

fentin acetate
IUPAC name triphenyltin(IV) acetate; triphenyltin acetate
Chemical Abstracts name (acetyloxy)triphenylstannane
CAS RN [900-95-8] EEC no. 212-984-0 Development codes Hoe 002782 (Hoechst); AE F002782 (Bayer CropScience) Official codes OMS 1020; ENT 25208

fentin hydroxide
IUPAC name triphenyltin(IV) hydroxide; triphenyltin hydroxide
Chemical Abstracts name hydroxytriphenylstannane
CAS RN [76-87-9] EEC no. 200-990-6 Development codes AE F029664 (Bayer CropScience) Official codes OMS 1017; ENT 28009

PHYSICAL CHEMISTRY
fentin
Mol. wt. 350.0 M.f. C18H15Sn

fentin acetate
Composition Tech. grade is ³94% pure. Mol. wt. 409.0 M.f. C20H18O2Sn Form Colourless crystals. M.p. 121-123 ºC; (tech., 118-125 ºC) V.p. 1.9 mPa (60 ºC) KOW logP = 3.54 Henry 2.96 ´ 10-4 Pa m3 mol-1 (20 °C, BBA method) S.g./density 1.5 (20 ºC) Solubility In water c. 9 mg/l (20 ºC, pH 5). In ethanol 22, ethyl acetate 82, hexane 5, dichloromethane 460, toluene 89 (all in g/l, 20 ºC). Stability Stable when dry. Converted to fentin hydroxide in the presence of water. Unstable in acids and alkalis (22 ºC), DT50 <3 h (pH 5, 7 or 9). Decomposed by sunlight and by atmospheric oxygen. F.p. 185? °C (Cleveland open cup)

fentin hydroxide
Composition Tech. grade is ³95% pure. Mol. wt. 367.0 M.f. C18H16OSn Form Colourless crystals. M.p. 123 °C V.p. 0.0013 mPa (50 ºC) KOW logP = 3.54 Henry 6.28 ´ 10-7 Pa m3 mol-1 (20 °C) S.g./density 1.54 at 20 ºC Solubility In water c. 1 mg/l (pH 7, 20 ºC), (greater at lower pH values). In ethanol 32, isopropanol 48, acetone 46, polyethylene glycol 41 (all in g/l, 20 °C). Stability Stable in the dark at room temperature. Dehydration occurs on heating above 45 ºC, yielding bis(triphenyltin) oxide, which is stable up to c. 250 ºC. Slowly decomposed by sunlight, and more rapidly by u.v. light, to give inorganic tin via di- and mono- phenyltin compounds. F.p. 174 °C (Cleveland open cup)

COMMERCIALISATION
History Fungicidal properties of organotin compounds investigated by G. J. M. van der Kerk & J. G. A. Luijten (J. Appl. Chem., 1954, 4, 314; 1956, 6, 56) and reviewed by H. Bock (Residue Rev., 1981, 79, 1). Fentin acetate was introduced by Hoechst AG (now Bayer CropScience) and fentin hydroxide by N.V. Philips-Duphar (now Crompton Corp.), both in 1959/1960.

fentin acetate
Patents US 3499086 (Hoechst)

APPLICATIONS
fentin acetate
Biochemistry Multi-site inhibitor, preventing spore germination, and inhibiting metabolism of the fungal organism, in particular respiration. Mode of action Non-systemic fungicide with mainly protective action, but also some curative action. Also acts as an algicide and molluscicide. Uses Control of early and late blights of potatoes (at 200-300 g/ha), leaf spot diseases of sugar beet (at 200-300 g/ha), anthracnose of beans (at 200 g/ha). Phytotoxicity Vines, ornamentals, some fruits, and glasshouse crops may be injured. Formulation types WP. Compatibility Incompatible with oil emulsions and EC formulations. Selected products: 'Suzu' (Nihon Nohyaku); mixtures: 'Brestan' (+ maneb) (Bayer CropScience)

fentin hydroxide
Biochemistry Multi-site inhibitor, preventing spore germination, and inhibiting metabolism of the fungal organism, in particular respiration. Mode of action Non-systemic fungicide with protective and curative action. Uses Control of early and late blights of potatoes (at 200-300 g/ha), leaf spot diseases of sugar beet (at 200-300 g/ha), and fungal diseases soya beans (at 200 g/ha). Phytotoxicity Non-phytotoxic when used as directed. Tomatoes and apples may be injured. Surfactants, spreaders or stickers should not be used, as this can lead to phytotoxicity. Formulation types SC; WP. Compatibility Not compatible with strongly acidic compounds. Incompatible with oils and liquid formulations. Selected products: 'Brestan' (Bayer CropScience); 'Super-Tin' (Chiltern, Griffin); 'Suzu-H' (Nihon Nohyaku)

OTHER PRODUCTS
fentin acetate
Discontinued products: 'Fentol' * (Bayer); 'Hokko Suzu' * (Hokko); 'Radar' * (Productos OSA)

fentin hydroxide
'Agri Tin' (Nufarm Ltd); 'Anticercospora' (Siapa); 'Brestanid' (Bayer CropScience); 'Duter' (BASF); 'Farmatin' (Bayer CropScience); 'Keytin' (Chiltern); 'MSS Flotin' (Nufarm UK); 'Rosette' (GreenCrop) mixtures: 'Pro-Tex' (+ maneb) (Griffin); 'Timbal F' (+ tetraconazole) (Sipcam Phyteurop) Discontinued products: 'Du Ter' * (Duphar, AgrEvo); 'Photon' * (Aventis); 'Ashlade Flotin' * (Ashlade) mixtures: 'EndSpray' * (+ metoxuron) (PBI)

ANALYSIS
Product analysis: fentin acetate and hydroxide may be determined by conversion to fentin chloride, followed by rplc with u.v. detection (CIPAC Handbook, 1992, E, 89-94), or by hydrolysis of fentin acetate to the hydroxide, which is measured by potentiometric titration (CIPAC Handbook, 1980, 1A, 1263, 1266; AOAC Methods, 17th Ed., 979.02), or by glc of a derivative (ibid., 984.04; CIPAC Handbook, 1983, 1B, 1837; ibid., 1988, D, 95; Van Rossum et al., Anal. Methods Pestic. Plant Growth Regul., 1980, 11, 227). Residues determined by atomic absorption spectrophotometry of total tin (W. H. Evans et al., Analyst (London), 1979, 104, 16; T. Ferri et al., Talanta, 1989, 36, 513) or by glc of a derivative (H. H. van den Broek et al., Analyst (London), 1988, 113, 1237; Van Rossum, loc. cit.; P. G. Baker et al., Analyst (London), 1980, 105, 282).

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 62, 64 (see part 2 of the Bibliography).

fentin
ADI (JMPR) 0.0005 mg/kg b.w. [1991].

fentin acetate
Oral Acute oral LD50 for rats 140-298 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 127 mg/kg. Irritating to skin and mucous membranes on repeated application. Inhalation LC50 (4 h) for male rats 0.044, female rats 0.069 mg/l air. NOEL (2 y) for dogs 4 mg/kg diet. ADI 0.0004 mg/kg b.w. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification R40| R63| T+; R26| T; R24/25, R48/23| Xi; R37/38, R41| N; R50, R53

fentin hydroxide
Oral Acute oral LD50 for rats 150-165 mg/kg. Skin and eye Acute percutaneous LD50 for rabbits 127 mg/kg. Irritating to skin and mucous membranes on repeated application. Inhalation LC50 (4 h) for rats 0.06 mg/l air. NOEL (2 y) for rats 4 mg/kg diet. ADI 0.0004 mg/kg b.w. Toxicity class WHO (a.i.) II; EPA (formulation) II EC classification R40| R63| T+; R26| T; R24/25, R48/23| Xi; R37/38, R41| N; R50, R53

ECOTOXICOLOGY
fentin acetate
Birds LD50 for quail 77.4 mg/kg. Fish LC50 (48 h) for fathead minnow 0.071 mg/l. Daphnia LC50 (48 h) 10 mg/l. Algae LC50 (72 h) 32 mg/l. Bees Formulation not toxic to bees. Worms LD50 (14 d) 128 mg/kg.

fentin hydroxide
Birds Dietary LC50 (8 d) for bobwhite quail 38.5 mg/kg diet. Fish LC50 (48 h) for fathead minnow 0.071 mg/l. Daphnia LC50 (48 h) 10 mg/l. Algae LC50 (72 h) 32 mg/l. Bees Not toxic to bees. Worms LD50 (14 d) 128 mg/kg.

ENVIRONMENTAL FATE
EHC 15 (WHO, 1980). Soil/Environment In soil, fentin acetate and fentin hydroxide are degraded to inorganic tin via di- and mono- phenyltin compounds. Soil DT50 c. 20 d (lab).