Silthiofam, silthiopham 硅噻菌胺

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中文通用名称: 硅噻菌胺
英文通用名称: silthiopham
商品名称: Latitude
试验代号: Mon 65500

化学名称:
N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide
N -烯丙基4,5-二甲基-2-三甲基硅噻吩-3-羧酰胺

CA主题索引名及CAS登录号:
3-thiophenecarboxamide, 4,5-dimethyl-N-(2-propenyl)-2-(trimethylsilyl)
[175217-20-6]

化学结构类型: 含硅的噻酚酰胺类
理化性质: 白色颗粒状固体,熔点为86.1~88.3℃,水中溶解度(20℃):35.3 mg/l。
毒性: 大鼠急性经口LD50:>5000mg/kg;大鼠急性经皮LD50(24小时):>5000mg/kg。本品对兔眼睛和皮肤无刺激。Ames试验、小鼠微核试验呈阴性。
作用机理: 具体作用机理尚不清楚,与三唑类、甲氧基丙烯酸酯类的作用机理不同,研究表明其是能量抑制剂:可能是A T P抑制剂。
防治对象: 小麦全蚀病
应用: 其具有良好的保护活性,残效期长。主要作种子处理,使用剂量为5-40g/100kg 种子。

合成方法:
以丁酮、氰基乙酸乙酯为起始原料,首先在硫磺存在下合环制中间体噻吩胺,经重氮化制得对应的溴化物;再经水解得羧酸;然后在丁基锂存在下与三甲基氯化硅反应,
最后与烯丙基胺酰氨化即得目的物。反应式为:

主要原料与中间体: 丁酮、氰基乙酸乙酯、三甲基氯化硅、烯丙基胺
分析方法: HPLC
开发公司: 孟山都公司
专利申请: US5486621

 

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silthiofam
Fungicide
FRAC U2, C7; thiophenecarboxamide

  silthiofam

NOMENCLATURE
Common name silthiofam (BSI, pa ISO)
IUPAC name N-allyl-4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide
Chemical Abstracts name 4,5-dimethyl-N-2-propenyl-2-(trimethylsilyl)-3-thiophenecarboxamide
Other names silthiopham CAS RN [175217-20-6] Development codes MON65500 (Monsanto)

PHYSICAL CHEMISTRY
Mol. wt. 267.5 M.f. C13H21NOSSi Form White, crystalline powder. M.p. 86.1-88.3 °C KOW logP = 3.48 (20 °C) Solubility In water 35.3 mg/l (20 °C).

COMMERCIALISATION
History Discovered in 1993-94 by Monsanto Co. Reported by R. E. Beale et al. (Proc. Br. Crop Prot. Conf. - Pests Dis., 1998, 2, 343). Introduced in Ireland in 1999. Patents EP 538231 Manufacturers Monsanto

APPLICATIONS
Biochemistry Inhibits transport of ATP from within the mitochondria to the cytosol (T. Joseph-Horne et al., Pestic. Biochem. Physiol. 67 168 (2000)). Mode of action Protectant fungicide with long-lasting control. Uses For antifungal seed treatment in cereals (wheat, barley and triticale). Applied at 25 g/100 kg seed. Formulation types FS. Selected products: 'Latitude' (Monsanto)

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Non-irritating to skin and eyes (rabbits). Other Negative in Ames, CHO/HGPRT gene mutation, in vitro cytogenicity and mouse micronucleus tests.

ENVIRONMENTAL FATE
Soil/Environment In soil, DT50 <365 d.