Natamycin 纳他霉素

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纳他霉素
英文名称: Natamycin(Pimaricin)
别名: 游霉素;匹马菌素;匹马利星
详情: 分子式:C33H47 NO13
分子量:665.73
理化性质:乳白色粉末,熔点280℃(分解)。不溶于水,微溶于甲醇,溶于稀盐酸、稀碱液、冰乙酸及二甲基甲酰胺。pH值低于3或高于9时,其溶解度可有所提高。对空气中氧、紫外线极为敏感,所以在使用或存放时应注意避光与密封。

来源与制法: 由纳他尔链霉菌经过发酵、提取、精制而得。
纳他霉素是一种多烯烃大环内酯类抗真菌剂,它对几乎所有的酵母菌和霉菌都有抗菌活性,不仅能够抑制真菌,还能防止真菌霉素的产生。 纳他霉素
其分子是一种具有活性的环状四烯化合物,含3个以上的结晶水,其外观白色(或奶油色),为无色、无味的结晶粉末,分子式C33H47NO13,分子量为665.73。微溶于水、甲醇,溶于稀酸、冰醋酸及二甲苯甲酰胺,难溶于大部分有机溶剂。在pH值高于9或低于3时,其溶解度会有所提高,在大多数食品的PH范围内非常稳定。纳他霉素具有一定的抗热处理能力,在干燥状态下相对稳定,能耐受短暂高温(100℃);但由于它具有环状化学结构、对紫外线较为敏感,故不宜与阳光接触。纳他霉素活性的稳定性受PH值、温度、光照强度和氧化剂及重金属的影响,所以产品应该避免与氧化物及硫氢化合物等接触。

 

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natamycin (BAN name).
Superseded record no. 1305
See The BioPesticide Manual, 2nd Ed.; entry 2:127

CAS RN [7681-93-8]. Structure established by B. T. Golding et al. (Tetrahedron Lett., 1966, p. 3551), W. E. Meyer (Chem. Commun., 1968, p. 470) and G. Gaudiano et al. (Chem. Ind. (Milan), 1966, 48, 1327). Stereochemistry revised, J. M. Lancelin & J. M. Beau, J. Am. Chem. Soc., 1990, 112, 4060, 6749; A. J. Duplantier & S. Masamune, ibid. , p. 7079. Introduced as a fungicide by Gist-Brocades N.V. Common names natamycin (BAN); pimaricin (traditional name); tennecetin (traditional name) IUPAC name (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-b-D-mannopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7 ]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid CA name [1R -(1R*, 3S*, 5R*, 7R*, 8E, 12R*, 14E, 16E, 18E, 20E, 22R*, 24S* 25R*, 26S* )]-22-[(3-amino-3,6-dideoxy-b-D-mannopyranosyl)oxy]-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.05,7 ]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid. Other names myprozine M.f. C33H47NO13 Composition Exists as a trihydrate. Tech. is >87%. Mol. wt. 665.7 (anhydrous) Form White crystals. M.p. 280-300 °C (decomp.) Solubility In water 4.1 g/l (20-22 ºC). In dimethyl sulfoxide >200, methanol 97, ethanol 5.5, acetone 0.85, petroleum spirit 0.1, benzene 0.05 (all in g/l, 20-22 ºC) (J. R. Marsh & P. J. Weiss, J. Assoc. Off. Anal. Chem., 1967, 50,457). Stability Stable when dry, but sensitive to light. Forms water-soluble salts with acids or alkalis.
Uses Control of diseases of bulbs, especially basal rot (Fusarium oxysporum ) of daffodils, preferably combined with a hot-water treatment. Formulation types WP. Products 'Delvolan' * (Gist-Brocades) . Details PM11 , Entry 515.