Patent GB-951770-A (GB)
Title: Improvements in or relating to combating pests
IPC: C07C255/49
Filed: 1960-04-27
Abstract: Nitro-chloro-benzonitriles of the general formula: <FORM:0951770/C2/1> where p=1 or 2, and p+q=5, may be produced by a series of reactions starting from the appropriate polychloro-benzonitrile or the appropriate nitro-polychlorobenzoic acid.  In Example 10, potassium nitrate is added to a solution of 2,4,6-trichlorobenzonitrile in concentrated sulphuric acid.  The mixture is heated for one hour, and then poured on ice and water whereby 3,5-dinitro-2,4,6-trichlorobenzoic acid is obtained. This acid is converted, via the acid-chloride, into the corresponding benzamide, which is then heated with phosphorus ocychloride to give 3,5-dinitro-2,4,6-trichlorobenzonitrile.  Example 11 describes the preparation of 2,6-dinitro-3,4,5-trichlorobenzonitrile by heating the corresponding benzamide with a mixture of phosphorus oxychloride and sodium dithionite.  The Specification also relates to nitro-chloro-benzonitriles outside the scope of the above formula. In Example 3, diazotised 2,4-dinitro-6-chloroaniline is treated with potassium nickel cyanide to give 2,4-dinitro-6-chlorobenzonitrile. Example 4 describes the preparation of 2-nitro-5,6-dichloro-benzonitrile by the action of cuprous cyanide on 2,3,4-trichloronitrobenzene.  Examples 1, 2, 8 and 9 relate to the preparation of three isomeric mononitro-trichlorobenzonitriles. Examples 5 and 7 relate to the preparation of 3,5-dinitro-2,6-dichlorobenzonitrile and 3,5-dinitro-4-chlorobenzonitrile, respectively.  Example 6 describes the preparation of 2,5-dinitrobenzonitrile by dehydration of 2,5-dinitrobenzamide.  All these compounds have use in the preparation of compositions for combating fungi and bacteria.ALSO:The invention comprises compositions for combating pests, such as fungi and bacteria, containing as an active substance a compound of the general formula <FORM:0951770/A5-A6/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p=1 or 2, q=1, 2, 3 or 4 when p=1, or q=0, 1, 2, 3 or 4 when p=2, and r=0, 1, 2 or 3.  Specified solid carriers are: chalk, dolomite, attapulgite, china clay and pipe clay.  Specific liquid carriers are: toluene, xylene, petroleum ether, acetone, methyl ethyl ketone and cyclohexanone. The compositions may incorporate insecticides, acaricides, fertilizers, surface-active agents, dispersion agents, and adhesives.  A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile (5 parts), kieselguhr (10 parts) and dolomite 85 parts), together to a mean particle size of about 10 microns.  A wettable powder may be produced by mixing 3,5-dinitro-2,4,6-trichlorobenzonitrile (20 parts), p  dolomite (73 parts), oleylamido-methyl-taurate (2 parts), and sodium lignin sulphonate (5 parts), and grinding the mixture to a mean particle size of about 10 microns.  A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile (10 parts) in a mixture of toluene (12 parts), methyl ethyl ketone (72 parts), and polyoxyethylenesorbitane fatty acid ester (6 parts). A dinitrobenzonitrile can also be used as active substance.ALSO:Pests such as fungi and bacteria are combated by treating seeds with a composition comprising as an active substance a compound of the general formula <FORM:0951770/A1-A3/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p = 1 or 2, q = 1, 2, 3 or 4 when p = 1, or q = 0, 1, 2, 3 or 4 when p = 2, and r = 0, 1, 2 or 3.  From tests with the seed of garden cress and a few monocotyledonous plants it has been found that the active substances do not retard germination.  A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile, kieselguhr, and dolomite together.  A wettable powder may be produced by grinding 3,5-dinitro-2,4,6-trichlorobenzonitrile, dolomite, oleylamido-methyl-taurate, and sodium lignin sulphonate together. A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile in a mixture of toluene, methyl ethyl ketone, and polyoxyethylenesorbitane fatty acid ester.  A dinitro-benzonitrile can also be used as an active substance.