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6-benzylaminopurine

6-benzylaminopurine NOMENCLATURE
Common name 6-benzylaminopurine (JMAF)
IUPAC name 6-benzyladenine 
Chemical Abstracts name N-phenylmethyl-1H-purin-6-amine 
Other names 6-BAP; 6-BA; BAP; N6-benzyladenine  CAS RN [1214-39-7]  EEC no. 214-927-5 

6-benzylaminopurine PHYSICAL CHEMISTRY
Composition Tech. is >99%.  Mol. wt. 225.3  M.f. C12H11N5  Form Colourless, odourless, fine needles; (tech. is an off-white powder).  M.p. 234-235 °C  V.p. 2.373 ´ 10-6 mPa (20 °C)  KOW logP = 2.13 (unstated pH)  Henry 8.91 ´ 10-9 Pa m3 mol-1 (calc.)  Solubility In water 60 mg/l (20 °C). Insoluble in most common organic solvents; soluble in dimethylformamide, dimethyl sulfoxide.  Stability Stable in acidic, alkaline and neutral aqueous solution. Stable to light and heat (8 h, 120 °C). 

6-benzylaminopurine COMMERCIALISATION
History Reported by C. G. Skinner et al., Plant Physiol.,33, 190-194 (1958). Introduced in Japan by Kumiai Chemical Industry Co., Ltd in 1975.  Manufacturers Cyclo; JIE; Jingma; Kohjin; Reanal

APPLICATIONS
Biochemistry Stimulates RNA, RuDP-Carboxylase, NADP-glyceraldehyde-3-phosphate-dehydrogenase, protein synthesis.  Mode of action Synthetic cytokinin; little translocated.  Uses Stimulates the following effects: cell division; lateral bud emergence (apples, pears, oranges); basal shoot formation (roses, orchids); flowering (cyclamen, cacti); fruit set (grapes, oranges, melons); causes abscission of young fruitlets, leading to increased fruit size, stimulates flower bud formation and regular bearing in fruit trees. Inhibits senescence of rice seedlings. Enhances lateral bud break and lateral shoot growth, leading to fuller white pine trees. Also causes uniform bolting and increased seed production in spinach. Applied by foliar application, soaking, or painting. Its limited ability to translocate is utilised to restrict effects to the target part of the plant, by local application. Applied at 30 g/a for apple trees. Formulation types PA; SL.  Selected products: 'BA' (Kumiai); 'Beanin' (Riken Green); 'Paturyl' (Reanal); mixtures: 'Accel' (+ gibberellin A4 with gibberellin A7) (Valent Biosciences); 'Promalin' (+ gibberellin A4 with gibberellin A7) (Valent Biosciences)

OTHER PRODUCTS
'Cyclex' (Valent Biosciences); 'Exilis' (Fine); 'ProShear' (Valent Biosciences) mixtures: 'ABG-3164' (+ gibberellin A4 with gibberellin A7) (Valent Biosciences); 'Perlan' (+ gibberellin A4 with gibberellin A7) (Fine, De Sangosse); 'Ritesize' (+ gibberellin A4 with gibberellin A7) (Nufarm Americas); 'Typy' (+ gibberellin A4 with gibberellin A7) (Nufarm Americas)

ANALYSIS
Analysis by glc and hplc with spectrophotometric detection. 

MAMMALIAN TOXICOLOGY
Oral Acute oral LD50 for male rats 2125, female rats 2130, mice 1300 mg/kg.  Skin and eye Acute percutaneous LD50 for rats >5000 mg/kg. Not a skin or eye irritant (rabbits); not a skin sensitiser.  NOEL (2 y) for male rats 5.2, female rats 6.5, male mice 11.6, female mice 15.1 mg/kg b.w. daily.  ADI 0.05 mg/kg.  Other Non-mutagenic in the Ames test. Non-teratogenic (rats and rabbits).  Toxicity class WHO (a.i.) U (company classification); EPA (formulation) III 

ECOTOXICOLOGY
Birds Practically non-toxic.  Fish LC50 (48 h) for carp >40 mg/l.  Daphnia LC50 (24 h) for D. carinata >40 mg/l.  Algae EC50 (96 h) 363.1 mg/l ('Paturyl' 10 SL formulation).  Bees LD50 (oral) 400 mg/bee, (contact) 57.8 l/ha (both 'Paturyl' 10 SL formulation). 

ENVIRONMENTAL FATE
Animals Almost all of administered 14C was excreted in urine and faeces. Three metabolites were identified.  Plants More than 9 metabolites were identified from metabolism studies in soya beans, grapes, maize and cocklebur. Urea is an end product.  Soil/Environment 16 Days after application to soil at 22 °C, 6-benzylaminopurine had degraded to 5.3% (sandy loam) and 7.85% (clay loam soil) of applied dose. Other studies indicate DT50 7-9 w.