Bilanafos 双丙氨膦

双丙氨膦

CAS号：35597-43-4
英文名称：bilanafos，Bialaphos
化学名称：4-(hydroxymethylphosphinyl)-L-2-aminobutanoyl-L-alanyl-L-alanine
其他名称： 双丙氨酰膦；；bilanafos-sodium，Meiji herbiace ； MW 801 ；SF 1293
分子式： C11H22N3O6P
分子量： 323.3

理化性质：　　 原药外观为浅棕色无味粉末，熔点160℃（分解），蒸气压（20℃）8.8×10－5Pa，易溶于水（1.0kg／L）、甲醇（0.5kg／L）、乙醇（2.5kg／L），不溶于丙酮、苯、正丁醇、氯仿、乙醚、己烷。在土壤中易失去活性。不易燃，无爆炸性，在强碱和强酸中不稳定，对光和热较稳定。

毒性：双丙氨膦钠盐对雄大鼠急性经口LD50为68mg／kg，雌大鼠LD50为404mg／kg，大鼠急性经皮LD50＞5000mg／kg，对兔眼睛和皮肤无刺激作用。试验结果表明，对大鼠无致畸作用，无致突变作用，无致癌作用。小鸡急性经口LD50＞5000mg／kg。鲤鱼LC50（48h）为l000mg／L，水蚤LC50（48h）为1000mg／L。

作用特点及杀草谱：　双丙氨膦是由一个不常见氨基酸phosphinothricin [L-2-氨基-4(羟基)(甲基)氧膦基丁酸，Pt]和两个丙氨酸构成的三肽，它不但具有除草活性，而且还具有一定的抗菌活性。Ptt的抗菌活性是由于其到达菌细胞后在细胞内肽酶的作用下而释放出Pt，由于Pt同谷氨酸结构的相似性，因此可以作为谷氨酰胺(GLn)合成酶的阻断剂而使谷氨酰胺的生物合成受阻，从而导致在植物体内氨的积累而使植物中毒死亡。

双丙氨膦为高效的抗生素类除草剂，属灭生性除草剂，可在杂草生长期作茎叶处理。无内吸传导性和选择性，对未出土的杂草无效。本剂可用于防除1年生和多年生千篇一律本科杂草和阔叶草，如芥菜、猪殃殃、雀舌草、繁缕、婆婆纳、葡萄冰草、看麦娘、野燕麦、藜、莎草、稗、早熟禾、马齿苋、车前、蒿、田施花、问荆等。对阔叶杂划的防除效果优于禾本科杂草。其作用比草甘膦快，比百草枯慢，而且对多年生植物有效，对哺乳动物低毒，在土壤中半衰期较短（20-30天）。可用于抗草丁膦和耐草甘膦的转基因作物田中。

施药方式与草甘膦相似，只能进行茎叶处理，不能进行土壤处理，在蔬菜田中防除一年生杂草，一般用32％可溶性浓剂0.2～0.33L／667m2加水喷雾，在果园中一般用量为32％可溶性浓剂0.33～0.5L／667m2，防除多年生杂草则应加大剂量至0.5～0.67L／667m2。还可茎叶喷雾防除橡胶园、柑橘园杂草。

剂型：20％双丙氨膦钠盐可溶性粉剂。

生产方法：　产生菌为从土壤中分离的链霉菌Streptomyceshygroscopicus,Sviridochromogenes亦可产生双丙氨瞵。吸水链霉菌（Streptomyceshygroscopicus）SF-1293在含有丙三醇、麦芽、豆油及痕迹量氯化钴、氯化镍、磷酸二氢钠的培养液中与D-L-2氨基-I-甲基磷基丁酸一起在28℃下振摇96h培养，培养物离心后，滤液经活性炭脱色，色谱柱分离，制得双丙氨磷。

生产情况：双丙胺膦是由日本明治制果株式会社研发的新型果园生物除草剂，由华北制药集团爱诺有限公司在全球独家生产，年生产能力可达50吨以上。

bilanafos
See also The BioPesticide Manual, 2nd Ed., entry 2:102
Herbicide
HRAC H WSSA 10; phosphinic acid

NOMENCLATURE
bilanafos
Common name bilanafos (BSI, draft E-ISO, (m) draft F-ISO); bialaphos (JMAF)
IUPAC name 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine
Other names bialaphos CAS RN [35597-43-4] Development codes MW-801; SF-1293

bilanafos-sodium
Common name bilanafos-sodium
IUPAC name sodium 4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alaninate
Chemical Abstracts name (2S)-2-amino-4-(hydroxymethylphosphinyl)butanoyl-L-alanyl-L-alanine, monosodium salt
CAS RN [71048-99-2] Development codes SF-1293Na; MW-851

PHYSICAL CHEMISTRY
bilanafos
Mol. wt. 323.3 M.f. C11H22N3O6P Solubility In water 1 kg/l. In methanol 500, ethanol 250 (both in g/l). Practically insoluble in organic solvents such as acetone, benzene, butan-1-ol, chloroform, diethyl ether, hexane. Stability Unstable in strong acids and strong alkalis. Specific rotation [a]D25 -34?(10 g/l water)

bilanafos-sodium
Mol. wt. 345.3 M.f. C11H21N3NaO6P Form Colourless crystals. M.p. c. 160 ºC (decomp.) Solubility In water >1000 g/l. In acetic acid 3.2, methanol 0.31 g/l; practically insoluble in organic solvents such as ethanol, acetone, chloroform and benzene. Stability Stable to light and heat. Unstable in strong acids and strong alkalis.

COMMERCIALISATION
Production Bilanafos is produced by fermentation of Streptomyces hygroscopicus. History Herbicidal activity of this fermentation product reported by K. Tachibana et al. (Abstr. 5th Int. Congr. Pestic. Chem., IVa, Abstract 19) and the compound reviewed by S. Mase (Jpn. Pestic. Inf., 1984, 45, 27). Introduced by Meiji Seika Kaisha Ltd. in 1984. Manufacturers Meiji Seika

APPLICATIONS
Biochemistry Inhibits glutamine synthetase activity, and causes accumulation of ammonia and inhibition of photosynthesis. Mode of action Non selective contact herbicide, absorbed by the foliage, with some systemic activity. Inactivated on contact with soil.

bilanafos-sodium
Uses Post-emergence control of wide range of annual and perennial broad-leaved weeds and grasses, in vegetable fields, orchards, vineyards, pre-planting in paddy fields, and non-crop land. Formulation types SL. Selected products: 'Herbie' (Meiji Seika, Hokko, Sumitomo Chemical Takeda)

OTHER PRODUCTS
bilanafos-sodium
Discontinued products: 'Herbiace' * (Meiji Seika)

ANALYSIS
Product by nmr. Residues by glc. Details from Meiji Seika.

MAMMALIAN TOXICOLOGY
bilanafos
Toxicity class WHO (a.i.) II

bilanafos-sodium
Reviews A. Suzuki et al., J. Pesticide Sci., 1987, 12, 347. Oral Acute oral LD50 for male rats 268, female rats 404 mg/kg. Skin and eye Acute percutaneous LD50 for rats >3000 mg/kg. Non-irritating to skin and eyes (rabbits). Inhalation LC50 for male rats 2.57, female rats 2.97 mg/l. Other In sub-acute and chronic toxicity studies, no ill-effects were observed. Non-carcinogenic, non-mutagenic and non-teratogenic. Not mutagenic in Ames and Rec assays.

ECOTOXICOLOGY
bilanafos-sodium
Birds Acute oral LD50 for chickens >5000 mg/kg. Fish LC50 (48 h) for carp >1000 mg/l. Daphnia LC50 (3 h) >5000 mg/l. Worms Not toxic to earthworms. Other beneficial spp. Not toxic to soil microorganisms.

ENVIRONMENTAL FATE
Animals In mice, the main metabolite in the faeces following oral administration was glufosinate (q.v.) (A. Suzuki et al., J. Pestic. Sci., 1987, 12, 105). Soil/Environment Rapidly degraded in soil and water.