Patent GB-892421-A (GB)
Title: Improvements in or relating to phytotoxic and insecticidal triazino compounds and preparations thereof
IPC: A01N43/66
Filed: 1958-04-02
Abstract: The invention comprises mono-chloro-triazines of the general formula <FORM:0892421/IV (b)/1< wherein X is oxygen or sulphur, Y is sulphur or the group -NH- and R1 and R2 are aliphatic or alicyclic hydrocarbon radicals having 3 to 7 carbon atoms, which radicals may be saturated or unsaturated.  They or their mineral acid salts may be prepared by one of the following methods.  Cyanuric acid chloride is reacted with a compound H-X-R1 or M(-X-R1)w and with a compound H-Y-R2 or M(-Y-R2)w in either order, M representing a uni- or polyvalent metal and w its valency.  Also, a dichlorotriazine <FORM:0892421/IV (b)/2> may be reacted with a compound H-Y-R2 or M(-Y-R2)w.  The reactants H-X-R1 and H-Y-R2 may be used in conjunction with acid-binding agents such as inorganic alkaline substances (including aqueous NaOH) or amines of various types; alkylated pyridines are preferred.  When the triazines containing the group -X-R1 are reacted with compounds H-NH-R2, the latter may be used in the form of their mineral acid salts.  In addition, disubstituted monochlor-triazines as above defined wherein R1 and R2 are identical and X and Y both represent sulphur may be prepared by reacting cyanuric chloride with a compound H-S-R1 or M(-S-R1)w.  The various reactions may be effected in the presence of inert solvents. The metal alcoholate and thiolate reactants may be used with a non-reacting excess of alcohol or thiol The compounds may be used as active ingredients for insecticidal and phytotoxic comcompositions (see Group VI).  In examples there are prepared by one or other of the above methods (1) 2-n-butoxy-4-isopropylamino-, -4-n-butyl thio- or -4-n-pentyl thio- 6-chloro-triazine and, (2) 2-n-butyl thio-4-isopropylamino-, -4-n-butyl thio- or 4(31-methyl butyl thio)-6-chlorotriazine.  Many other such compounds are named including some wherein R1 or R2 represents the cyclohexyl radical. Specifications 755,468 and 818,437 and U.S.A. Specification 2,513,264 are referred to.ALSO:Phytotoxic and insecticidal compositions comprise in admixture with an inert carrier or diluent, a mono-chlor triazine of the general formula <FORM:0892421/VI/1> wherein X is oxygen or sulphur, Y is sulphur or the group -NH- and R1 and R2 are aliphatic or alicyclic hydrocarbon radicals containing 3-7 carbon atoms and which may be saturated or unsaturated.  The carrier or diluent may be a solid such as alumina, diatomaceous earth, kaolin, dolomite, talcum, gypsum, chalk, bentonite, attapulgite, infusorial earth wood flour, tobacco dust and ground coconut shells.  Liquid diluents may be used including water, dioxane and numerous specified hydrocarbon solvents.  The compositions may be in emulsion or dispersion form and contain as surface-active agents alkyl-phenoxy-polyglycol ethers, polyoxyethylene-sorbitan or -sorbitol esters of fatty acids, lignin sulphonates, fatty alcohol sulphates, alkyl-aryl sulphonates, naphthalene sulphonates and fatty acid condensation products.  The compositions may comprise acid-binding agents such as propylene oxide.  In examples: (7) 2-n-butoxy-4-n-butyl thio-, -4-n-pentyl thio- or -4-n-butyl thio-6-chlorotriazine, propylene oxide and an emulsifier are mixed with xylene providing an oil dilutable with water to give a weed-killing emulsion; (8) an aerosol comprises any of the triazines of (7), xylene, propylene oxide, methylene chloride and a fluoro-chloro-methane.  Numerous other triazines are specified including a number having the above general formula wherein R1 or R2 represents the cyclohexyl radical and one wherein R1-X- and R2-Y- both represent n-buty lthio.  Their preparation is described (see Group IV (b)). Specifications 755,468 and 818,437 and U.S.A. Specification 2,513,264 are referred to.