Patent GB-1086522-A (GB)
Title: Phenazines and biocidal compositions containing same
Inventor: HACKMANN JOHANNES THOMAS
IPC: C07D241/52
Filed: 1964-09-03
Abstract: The invention comprises the following phenazine derivatives: 1,4 - dibromo-, 1,2,3 - trichloro-, 1,2,4-trichloro-, 2-ethyl-, 1-isopropyl-, 2-isopropyl-, 2-n-butyl-, 2-n-pentyl-, 2-n-hexyl-, 2-n-heptyl-, 1-methyl-3-(11, 11, 31, 31 -tetramethyl-butyl)-, 2-methyl-7(or 8)-t-octyl-, 1,4-dimethyl-, 2,3-dimethyl-7-t-octyl-, 1,7(or 8)-dimethyl-, 1-methyl -3-t-butyl, 2,3,7-trimethyl, 1,3-diisopropyl-, 2-n-propoxy-, 2-n-butoxy-, 2-n-pentyloxy-, 2-azido-, 1,2,3,4-tetrafluoro-7 -(11,11,31,31-tetramethylbutyl-, 2-thiocyanato-, 2-t-octyl-7(or 8)-chloro-, 1-bromo-3-t-octyl-, 1-chloro-3-t-octyl-, 2 - n - stearyl-, 2 - n - octyl-, 2 - n - lauryl-, 2,3-dimethyl - 7 - (11,11,31,31 - tetramethylbutyl)-, 1 - bromo - 3 - (11,11,31,31 - tetramethylbutyl)-, 1 - chloro - 3 - (11,11,31,31 - tetramethylbutyl)-, 2 - (11,11.31,31 - tetramethylbutyl) - 7(or 8)-methyl-, 2 - (11,11.31,31 - tetramethylbutyl)-7(or 8)-chloro-, and 1,4,7-trichlorophenzines and 2-isopropyl-phenazine-, 5,10-dioxide and 1,4 - dimethylphenazine - 5 - oxide.  The compounds are prepared by adding a solution of the appropriate orthophenylenediamine and the appropriate catechol to a suspension, in the solvent, of an oxide of a metal of Group IB, IIB or VIIB, preferably manganese dioxide or mercuric oxide.  There are also disclosed phenazines of the general formula <FORM:1086522/C2/1> of the mono- or di-N-oxides thereof, in which n and m are 0 or 1-4, and m + n is at least 1, and R1 and R2 are halogen, or a C1- 2 alkyl, aryl, alkaryl, aralkyl or alkoxy group which may be substituted by 1 or more halogen or hydroxy groups, or a hydroxy, cyano, thiocyanato, azido, nitro, amino, or a mono- or di-alkyl-amino group, or when 2 R substituents are on adjacent carbon atoms they may complete a benzene ring which may be substituted by halogen and/or alkyl groups; these compounds are prepared by a similar method. Numerous examples are provided some of which relate to phenazines other than those specific compounds listed above.ALSO:Crops are protected against attack by fungi, acarids or competition by weeds, by treating crops subject or subjected to such attack, weeds providing such competition or soil in which such weeds or crops are growing or are to be grown, with a fungicidally, acaricidally or herbicidally effective amount of a composition comprising an acaricidally, fungicidally or herbicidally acceptable carrier and/or surface active agent and at least one phenzine of the formula <FORM:1086522/A5-A6/1> or the mono- or di-N-oxide thereof, wherein n and m are 0, or 1-4, provided that m+n is at least 1, and R1 and R2, which may be the same or different, represent halogen or a C1-25 alkyl, aryl, aralkyl or alkaryl group optionally substituted by halogen or hydroxy groups, or a C1-25 alkoxy group, of a hydroxy, cyano, thiocyanato, azido, nitro, amino or mono- or dialkylamino group, or two R's on adjacent carbon atoms complete a benzene ring which may be substituted by an alkyl and/or halogen group.  The invention also includes compositions comprising an acaricidally, fungicidally or herbicidally acceptable carrier and, as active component, one of a number of specific phenazones having the above formula.  Specified carriers are clays, silicates, synthetic hydrated silicon oxides, resins, waxes, synthetic polymeric materials or elemental substances, water, alcohols, ketones, aromatic hydrocarbons, chlorinated hydrocarbons, petroleum fractions and dimethylsulphoxide.  The compositions may also include stabilisers, fertilisers and/or other unspecified biocides and may take the form of wettable powders, dusts, granules, concentrates, solutions, emulsifiable concentrates and invert emulsions.