Fenbutatin-Oxide 苯丁锡

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苯丁锡

CAS编码: 13356-08-6
商品名称:Torque, Vendex
通用名称:Fenbutatin Oxide
中文通用名称: 苯丁锡
中文商品名称: 苯丁基锡;芬布赐[台]; 克螨锡; 螨完锡[台]; 螨烷锡; 托尔克[氰胺]
化学名称:双[三(2-甲基-2-苯基丙基)锡]氧化物
分子式:C60H78OSn2
分子量:1052.67
外观:白色或淡黄色粉末晶体
熔点:137-138℃
溶解度(g/L20℃):二氯甲烷380,苯140
稳定性:对酸、光和热稳定

苯丁锡(fenbutatin oxide)
感温型抑制神经组织的有机锡杀螨剂。商品名有托尔克、Torque、Vendex、Osdaran等。
原药为无色晶状粉末,有效成分含量达97%,熔点138-139℃,25℃时蒸气压为6.7×10-6帕。难溶于水,溶于丙酮,易溶于苯、二氯甲烷等有机溶剂。对光和热稳定,遇水能被水解,水解产物在室温下能缓慢地(在98℃能很快地)再转变成原化合物。在合适的条件下贮存较稳定。对高等动物低毒,对鱼类等水生生物高毒,对鸟类、蜜蜂低毒,对害螨天敌捕食螨、食虫瓢虫、草蛉等较安全。杀螨活性较高,主要起触杀作用,对幼螨和成、若螨杀伤力较强,对螨卵的杀伤力不大,对有机磷、有机氯杀虫剂有抗药性的害螨无交互抗药性。属感温型杀螨剂,气温在22℃以上时药效增加,22℃以下时活性降低,15℃以下时药效较差,不宜在冬季使用。施药后药效作用发挥较慢,3天后活性开始增强,14天可达高峰,残效期较长,可达2-5个月。?
加工成可湿性粉剂和胶悬剂等剂型使用,可用于果树、茶树、花卉等作物,防治柑桔叶螨、柑桔锈螨、苹果叶螨、茶橙瘿螨、茶短须螨、菊花叶螨玫瑰叶螨等。喷雾要均匀,因药效作用发挥较慢,须根据虫情预测预报提前用药。

作用特点
是一种非内吸杀螨剂,对有机磷和有机氯有抗性的害螨对其不产生交互抗 性。对害螨以触杀为主,喷药后起始毒力缓慢,3天后活性开始增加,到14 天达到高峰。该药残效期是杀螨剂中较长的一种,可达2-5个月,对幼螨和 成、若螨的杀伤力较强,但对卵的杀伤力不大,在作物各生长期使用都很安 全,使用超过有效杀螨浓度一倍均未见有药害发生,对害螨天敌如捕食螨、 瓢甲和草蛉等影响甚小。当气温在22℃以下活性降低,低于15℃药效较低, 冬季不宜使用。

 

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fenbutatin oxide
Acaricide
IRAC 12B; organotin acaricide

  fenbutatin oxide

NOMENCLATURE
Common name fenbutatin oxide (BSI, E-ISO, JMAF); fenbutatin-oxyde ((m) F-ISO)
IUPAC name bis[tris(2-methyl-2-phenylpropyl)tin] oxide
Chemical Abstracts name hexakis(2-methyl-2-phenylpropyl)distannoxane
CAS RN [13356-08-6] EEC no. 236-407-7 Development codes SD 14 114 (Shell) Official codes ENT 27 738

PHYSICAL CHEMISTRY
Mol. wt. 1052.7 M.f. C60H78OSn2 Form Colourless crystals. M.p. 140-145 °C B.p. decomp. 230-310 °C V.p. 3.9 ´ 10-8 mPa (20 °C) KOW logP = 5.2 Henry 3.23 ´ 10-3 Pa m3 mol-1 (calc.) S.g./density 1290-1330 kg/m3 (20 ºC) Solubility In water 0.0127 mg/l (20 ºC). In acetone 6, benzene 140, dichloromethane 310 (all in g/l, 20 ºC). Very slightly soluble in aliphatic hydrocarbons and mineral oils. Stability Extremely stable to heat, light, and atmospheric oxygen; photostability DT50 51 d (pH 7, 25 ºC). Water causes conversion of fenbutatin oxide to tris(2-methyl-2-phenylpropyl)tin hydroxide, which is reconverted to the parent compound slowly at room temperature and rapidly at 98 ºC. F.p. Not autoflammable, but tech. will explode in a dust cloud if ignited

COMMERCIALISATION
History Introduced in USA by Shell Chemical Co. (now DuPont Agricultural Products) and elsewhere by Shell International Chemical Co., Ltd (now BASF AG). Patents US 3657451 Manufacturers BASF; Griffin

APPLICATIONS
Biochemistry Inhibitor of oxidative phosphorylation; disruptor of ATP formation. Mode of action Non-systemic acaricide with contact and stomach action. Uses Control of all motile stages of a wide range of phytophagous mites on pome fruit, stone fruit, citrus fruit, soft fruit, vines, bananas, cucurbits, ornamentals, and glasshouse crops. Gives long residual control. Phytotoxicity Phytotoxic to tangerines, tangelos, and some varieties of grapefruit. Otherwise, non-phytotoxic when used as directed. Formulation types SC; WP. Selected products: 'Osadan' (Japan only) (BASF); 'Torque' (BASF); 'Vendex' (Griffin)

OTHER PRODUCTS
'Torq' (Fargro) mixtures: 'Mitedown' (+ polynactins) (Eiko Kasei)

ANALYSIS
Product analysis by potentiometric non-aqueous titrimetry (CIPAC Handbook, 1988, D, 77). Residues determined by glc with ECD or FPD of suitable derivative (Anal. Methods Pestic. Plant Growth Regul., 1978, 10, 139; Methodensammlung Rückstandsanal. Pflanzenschutzmitteln, 1987, S24; M. Sano et al., J. Assoc. Off. Anal. Chem., 1979. 62, 764). Details available from BASF.

MAMMALIAN TOXICOLOGY
Reviews FAO/WHO 65, 67 (see part 2 of the Bibliography). Oral Acute oral LD50 for rats 3000-4400, mice 1450, dogs >1500 mg/kg. Skin and eye Acute percutaneous LD50 for rats >1000 mg/kg. Irritating to skin and severely irritating to eyes. Inhalation LC50 for rats 0.46-0.072 mg/kg b.w. NOEL (2 y) for rats 50 mg/kg b.w., for dogs 15 mg/kg daily. ADI (JMPR) 0.03 mg/kg b.w. [1992]. Toxicity class WHO (a.i.) U; EPA (formulation) III EC classification T+; R26| Xi; R36/38| N; R50, R53

ECOTOXICOLOGY
Birds Dietary LC50 (8 d) for bobwhite quail 5065 mg/kg diet. Fish LC50 (48 h) for rainbow trout 0.27 mg a.i./l (as WP formulation). Daphnia LC50 (24 h) 0.05-0.08 mg/l. Algae (72h) for Selenastrum capricornutum >0.005 mg/l. Bees Acute LD50 (contact and oral) >200mg/bee. Other beneficial spp. No adverse effects to a wide range of predatory and parasitic arthropods.

ENVIRONMENTAL FATE
Soil/Environment In soil, it is metabolised to dihydroxy-bis(2-methyl-2-phenylpropyl)stannane and 2-methyl-2-phenylpropyl stannonic acid, presumably ultimately forming tin oxide/hydroxide. In tests in commercial use, there was minimal movement of fenbutatin oxide or its metabolites out of the top 30 cm of soil (A. Gray et al., Pestic. Sci., 43, 295-302 (1995)).