Patent GB-818437-A (GB)
Title: Improvements in or relating to phytotoxical and insecticidal preparations and compounds
IPC: A01N43/66
Filed: 1957-06-14
Abstract: The invention comprises 2-substituted-4 : 6-dichloro-1 : 3 : 5-triazines of the general formula <FORM:0818437/IV (b)/1> where X is O or S and R is a saturated or unsaturated aliphatic or saturated alicyclic hydrocarbon radical containing at least two carbon atoms. The substituted triazines may be prepared by reacting cyanuric chloride with a compound of the general formula RXH, preferably in the presence of an acid binding agent.  The preparation may be carried out in an anhydrous medium such as chloroform, carbon tetrachloride, acetone, an aliphatic ether or an aromatic hydrocarbon and using an N-dialkyl aniline, 2-methyl quinoline or preferably an alkyl pyridine such as collidine as the acid binding agent.  The preparation may also be carried out in an aqueous medium using sodium carbonate, bicarbonate or hydroxide as the acid binding agent. Alternatively the substituted triazines may be prepared by treating cyanuric chloride with an alkali metal derivative of the alcohol or mercaptan, M-X-R, where M is an alkali metal atom, preferably in the presence of an excess of the parent alcohol or mercaptan.  The preparation is preferably carried out in the temperature range - 20 DEG  to + 25 DEG  C.  The examples describe the preparation in an anhydrous medium of the (1) ethoxy, (2) n-propoxy, (3) isopropoxy, (4) propene 2-oxy-1, (5) propyne-2-oxy-1, (6) n-butoxy, (7) 1-methyl propoxy, (8) cyclohexoxy, (9) octoxy, (10) 1 methyl heptoxy, (11) ethylmercapto, (12) n-propylmercapto, (13) isopropylmercapto, (14) allylmercapto, (15) n-butyl mercapto, (16) 1 : 1-dimethylethylmercapto, (17) 3-methylbutyl mercapto, and (18) n-octyl mercapto compounds.ALSO:The invention comprises phytotoxical and insecticidal preparations containing as active constituent a 2 - substituted - 4 : 6 - dichloro-1 : 3 : 5-triazine of the general formula <FORM:0818437/VI/1> where X is O or S and R is a saturated or unsaturated aliphatic or saturated alicyclic hydrocarbon radical. The triazines may be prepared by condensing cyanuric chloride with an alcohol or mercaptan (see Group IV (b)).  The phytotoxic and insecticidal effects of these preparations are found to be greatest when R contains between 2 and 11 carbon atoms and the results of tests carried out to demonstrate these effects are tabulated.  The active compounds may be mixed with or dissolved in solid or liquid carriers and dispensing agents, emulsifying agents and/or wetting agents may be added.  The preparations may be sprayed, pulverized or nebulized in air or may be emulsified or dispersed in a liquid such as water.  Mixable oils may be produced by dissolving the active compound in a water-immiscible solvent and adding an emulsifier. Siutable solvents include xylene, toluene, dioxane, petroleum distillates such as solvent naphtha or distilled tar oil, tetrahydronaphthalene or cyclohexane.  The emulsifier may be an alkyl-phenoxy-polyglycol ether, or polyoxyethylene sorbitane ester of a fatty acid or a polyoxyethylene sorbitol ester of a fatty acid. The concentration of active compound may vary from between 2 and 50 per cent by weight.  Spray powders may be prepared by mixing the active compound with an inert carrier such as alum earth, diatomaceous earth, kaolin, dolomite, talcum, gypsum, chalk, bentonite, attapulgite, infusorial earth, celite, wood meal, tobacco dust or ground coconut shells, usually in the presence of a dispersing agent such as a lignin or naphthalene sulphonate and/or a wetting agent such as a fatty alcohol sulphate, alkanyl sulphonate or an "Igepon" (Registered Trade Mark) wetting agent.  The concentration of active compound may vary between 10 and 80 per cent by weight.  To avoid splitting-off of hydrogen chloride from the active compounds 1 to 5 per cent of a hydrochloric acid binder such as propylene oxide may be added to the preparations.  In examples: (19) 2-n-butyl mercapto-4 : 6-dichloro-1 : 3 : 5-triazine is dissolved in xylene and an alkyl-phenoxy polyglycol ether emulsifier and propylene oxide added to give a mixable oil pherbicide, the 2-n-butoxy and 2-allyloxy compounds may be similarly used; (20) an aerosol insecticide is produced using the 2 - n - butyl - mercapto - (or 2(31 - methylbutyl)-mercapto- or 2-butoxy compound, xylene, propylene oxide, methylene chloride and a fluoro-chloro-methane compound.