Patent GB-940921-A (GB)
Title: Improvements in or relating to phosphorus-containing derivatives of compounds having a cyclic-nitrogen-containing heterocyclic nucleus of aromatic character
IPC: C07F9/572
Filed: 1959-10-21
Abstract: The invention comprises compounds of the general formula: <FORM:0940921/C2/1> wherein Q is the radical of a substituted or unsubstituted condensed or non-condensed compound having a cyclic nitrogen-containing heterocyclic nucleus of aromatic character, which nucleus contains an > NH group, of which group, in the compounds of the above formula the hydrogen atom is replaced by the group: <FORM:0940921/C2/2> in which formula X is oxygen or sulphur, and R1, R2, R3 and R4 are aliphatic hydrocarbo radicals, or R1 and/or R3 represents hydrogen and the remainder of R1, R2, R3 and R4 represent such aliphatic hydrocarbon radicals. The radical Q may be derived from pyrrole, pyrazole, imidazole, a triazole e.g. 1, 2, 3 or 1, 2, 4 triazole, tetrazole, indole, carbazole, benzpyrazole (indazole), benzimidazole, 2-alkylbenzimidazole or benztriazole.  Specified substituents on one or more carbon atoms of the heterocyclic nucleus are substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkylamino, dialkylamino, arylamino, diarylamino, acylamino, alkoxy, and alkylmercapto-groups containing up to 18 carbon atoms, halogen atoms, e.g. chlorine, nitro, amino, ureido, carboxy, carbalkoxy and sulphonic groups.  The groups R1, R2, R3 and R4 are preferably C1-C5 alkyl groups, especially methyl groups. They may be obtained by reacting a heterocyclic compound QH, preferably in the presence of a hydrogen halide binder, or a metal derivative of such compound in which the H of the NH group is replaced by a metal atom, e.g. Na or K, with a compound of the formula: <FORM:0940921/C2/3> in which Hlg is halogen, preferably Cl, X is O or S and n is 0 or 1 and Y1 and Y2 are both halogen or Y1 is a group -NR1R2 and Y2 is halogen or is -NR3R4, followed, if Y1 and/or Y2 are halogen atoms by reacting the product with a mono- or dialiphatic hydrocarbyl amine and/or if n=0 subjecting the product to oxidation, e.g. with hydrogen peroxide, when X is to be oxygen or to reaction with sulphur when X is to be sulphur.  Another method which may be used when X is oxygen is by the reaction of the heterocyclic compound QH with an alkylamidopyrophosphate. The reactions may be carried out in the presence of a diluent or solvent for the compound QH, e.g. an aliphatic or aromatic hydrocarbon, an aliphatic ether, a tertiary amine, a nitrile, a ketone, an ester, an alcohol, nitrobenzene, carbon tetrachloride or dimethylformamide. The reactions with the phosphorus halides should be carried out in an anhydrous medium. Several examples are given and the products have pesticidal properties (see Division A5). Specification 888,686 is referred to.ALSO:A composition for combating noxious organisms e.g. fungi, insects or mites, contains as active ingredient a compound of the general formula <FORM:0940921/A5-A6/1> wherein Q is the residue of a substituted or unsubstituted, condensed or non-condensed compound having a cyclic nitrogen-containing heterocyclic nucleus of aromatic character, which nucleus contains an > NH group, of which, in the compounds of the above formula the hydrogen atom is replaced by the group <FORM:0940921/A5-A6/2> in which formula X is oxygen or sulphur and R1, R2, R3 and R4 are aliphatic hydrocarbon radicals, or R1 and/or R3 represents hydrogen and the remainder of R1, R2, R3 and R4 represent such aliphatic hydrocarbon radicals (see Division C2).  The radical Q may be derived from pyrrole, pyrazole, imidazole, a triazole e.g. 1, 2, 3 or 1, 2, 4-triazole, tetrazole, indole, carbazole, benzpyrazole (indazole), benzimidazole, 2 - alkylbenzimidazole or benztriazole.  Specified substituents on the heterocyclic nucleus are substituted or unsubstituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, aralkenyl, alkylamine, dialkylamino, arylamino, diarylamino, acrylamino, alkoxy, and alkylmercapto groups, containing up to 18 carbon atoms, halogen atoms, e.g. chlorine, and nitro, amino, ureido, carboxy, carbalkoxy and sulphonic groups.  The groups R1, R2, R3 and R4 are preferably C1-C5 alkyl groups.  The composition may be obtained by mixing or dissolving the active ingredient with or in a solid or liquid carrier and a dispersion agent, emulsifier and/or wetting agent may also be present. Specified solvents are xylene, toluene, dioxane, petroleum distillates e.g. solvent naphtha, distilled tar oil, tetrahydronaphthalene, cyclohexane, and mixtures of such solvents. Specified solid carriers include pipe clay, wood meal, tobacco dust and ground coconut shells as well as the conventional carrier materials.  Specification 888,686 is referred to.