Patent GB-907811-A (GB)
Title: Process for the treatment of seed and fungicides for use therein
Inventor: GEOGHEGAN MICHAEL JOSEPH AUGUS
IPC: A01N33/26
Filed: 1958-03-05
Abstract: The invention comprises monoazo compounds of formula: -<FORM:0907811/IV (b)/1> wherein B is a benzene residue containing as substituent one or more alkyl, alkoxy or amino radicals and Y stands for a hydroxyl group in p-position to the azo group.  They are prepared by coupling a p-acylaminobenzenediazonium salt with a phenol containing as substituent one or more alkyl, alkoxy or amino radicals and then removing by hydrolysis the acyl radical.  The compounds are used in fungicidal seed-dressing compositions (see Groups I and VI). In an example the monoazo compound p-aminoacetanilide --> 2:6-dimethylphenol is prepared and hydrolysed with aqueous sodium hydroxide solution to give 4-amino-31:51-dimethyl- 41-hydroxyazobenzene: 4-amino-31-methyl-, 4-amino-21-methyl-, 4-amino-21- or -31-methoxy-, 21:4-diamino-, 4-amino-31:51-dimethoxy- and 4-amino-31-ethoxy-41-hydroxyazobenzenes are similarly prepared. The preparation of 2:4:41-triaminoazobenzene and 4-amino- 41-hydroxyazobenzene by similar methods is described.ALSO:Seeds are treated, before sowing, with a fungicidal and/or bactericidal seed dressing containing as the active ingredient an azocompound of formula:-  <FORM:0907811/I/1> wherein Ar is a benzene or naphthalene residue, which may be substituted by one or more alkyl, alkoxy, amino or hydroxy groups, and X is an amino or hydroxy group linked in p-position to the azo group (see Group VI).  Specified seeds are: pea, cotton, beet, sugarbeet, bean, maize and brassica seeds. Specified azo compounds are: 4-amino-21 : 41-dehydroxyazobenzene, 2 : 4 : 41-triaminoazobenzene, 4-(p-aminophenylazo)-1-napththylamine, 4 : 41-diamino-2-methyl-5-methoxyazobenzene, 4-(p-aminophenylazo)-1-napthhol, 4,amino-31-methyl-41-, 4-amino-21-methyl-41-, 4-amino-31-methoxy-41-, 4-amino-21-methoxy-41-, 4-amino-31 : 51-dimethoxy-41-, 4-amino-31-ethoxy-41-, 21 : 4-diamino-41-, 4-amino-31 : 51-dimethyl-41-and 4-amino-41-hydroxyazobenzene. The dressing may be a powder comprising, also, one or more of the following: talc, china clay, gypsum, basic slag, kieselguhr, bentonite, a mineral oil, a binder, a sticking agent, a wetting agent.  The dressing may be a solution of the azo compound in an organic solvent such as acetone, diacetone alcohol, or dimethylformamide.  These solutions may be dispersed in water.ALSO:The invention comprises fungicidal seed-dressing compositions containing as active ingredient an azo compound of formula <FORM:0907811/VI/1> wherein Ar is a benzene or naphthalene residue which may be substituted by one or more alkyl, alkoxy, amino or hydroxy radicals and X is an amino or hydroxy radical linked in the p-position to the azo group.  The compositions may be powders containing diluents such as talc, china clay, gypsum, basic slag, kieselguhr or bentonite.  The compositions may also contain other ingredients such as mineral oil or sticking, binding or wetting agents.  The compositions may also be solutions or dispersions in aqueous or organic solvent media, e.g. acetone, diacetone alcohol or dimethylformamide.  In examples, the preparation of solid compositions containing 4 - amino - 31 : 51 - dimethyl- and 4-amino-41-hydroxyazobenzenes and 2 : 4 : 41-triaminoazobenzene is described.