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    New biocidal bis (dimethylamido) phosphorylamino-triazole-1, 2, 4 derivatives
    5.
    发明授权
    New biocidal bis (dimethylamido) phosphorylamino-triazole-1, 2, 4 derivatives 失效
    新的杀生物双（二甲基氨基）磷酰氨基 - 三唑-1,2,4-衍生物

    公开(公告)号：US3213103A

    公开(公告)日：1965-10-19

    申请号：US25624663

    申请日：1963-02-05

    申请人： PHILIPS CORP

    发明人： DEN BOS BERNARDUS GERHARDUS VA ,  JACQUES MELTZER

    IPC分类号： C07D249/14 ,  C07F9/6518

    CPC分类号： C07F9/65181

    摘要： The invention comprises compounds of the general formula (or a tantomeric form thereof) in which X is a C2-C6 alkyl group or a phenyl group and R is a C1-C4 alkyl group or a phenyl, chlorophenyl- or methoxyphenyl group or such phenyl or substituted phenyl group containing a methyl group as a nuclear substituent. They may be obtained by reacting an amino-triazole derivative of formula or a tautomer thereof or a metal compound of such derivative in which the H atom of the >NH group in the nucleus is replaced by a metal, e.g. Na or K, with a compound of the general formula:- wherein Hlg is a halogen atom, e.g. Cl, n = O or 1 and Y1 and Y2 are halogen, e.g. Cl, or each is a -N(CH3)2 group or Y1 is N(CH3)2 and Y2 is halogen, and then if n = 1 and Y1 and Y2 are halogen atoms, reacting the resulting product with dimethylamine, or, if n = 1, Y1 is N(CH3)2 and Y2 is halogen reacting the resulting product with dimethylamine or if n = 0 and Y and Y2 are halogen atoms reacting the resulting product with dimethylamine followed by oxidation, or if n = 0, Y1 is N(CH3)2 and Y2 is halogen reacting the resulting product with dimethylamine followed by oxidation, or if n = 0 and Y1 and Y2 both represent -N(CH3)2, oxidizing the resulting product. The reaction between the aminotriazole derivative and the phosphorus halide compound IV is preferably carried out in the presence of a halogen-hydracid binding agent, e.g. a tertiary alkylamine, an N,N-dialkyl aniline, pyridine or homologue thereof or a metal or ammonium compound, and any subsequent oxidation step may be carried out with H2O2. The condensation reactions may be carried out in a solvent, e.g. an aliphatic or aromatic hydrocarbon, an aliphatic ether, a tertiary amine, a nitrile, ester, ketone, alcohol, nitrobenzene, CCl4 or dimethylformamide. The products have insecticidal properties and are also effective in combating moulds.ALSO:A composition for combating noxious organisms, e.g. insects, red spider or mildew contains as active ingredient a compound of the following general formula (or tautomeric form thereof): in which X is a C2-C6 alkyl group or a phenyl group and R is a C1-C4 alkyl group or a phenyl, chlorophenyl or methoxyphenyl group or such phenyl or substituted phenyl group containing a methyl group as a nuclear substituent (see Division C2). The composition may comprise the active ingredient in admixture with a liquid or solid carrier with or without a surface-active agent e.g. a dispersion, emulsifying and/or wetting agent and may be in the form of a dust, miscible oil or wettable powder. Specified solvents for use in preparing miscible oils are xylene, toluene, dioxane, petroleum distillates rich in aromatics, tetrahydronaphthalene and cyclohexane. Specified solid carriers include pipe clay, chalk, sawdust, tobacco dust, and ground coconut shells.

    Amino-triazol derivatives
    8.
    发明授权
    Amino-triazol derivatives 失效
    氨基三唑衍生物

    公开(公告)号：US3121090A

    公开(公告)日：1964-02-11

    申请号：US73013058

    申请日：1958-04-22

    申请人： PHILIPS CORP

    发明人： JOHANNES KOOPMANS MARTINUS ,  JACQUES MELTZER ,  OBIAS HUISMAN HENDERIKUS ,  DEN BOS BERNARDUS GERHARDUS VA ,  KOBUS WELLINGA

    IPC分类号： C07D249/14 ,  C07F9/6518

    CPC分类号： C07F9/65181

    摘要： The invention comprises compounds which are derivatives of an amino-triazol of the general formula or of a tautomeric form thereof, in which derivatives the phosphorus atom is bound to one of the nitrogen atoms of the triazol ring, and in which R1, R2, R3 and R4 designate aliphatic hydrocarbon radicals, X is oxygen or sulphur, and R5 designates a hydrogen atom, an alkyl, cycloalkyl, aryl, or aralkyl group or such group containing one or more substituents, or is an aliphatically unsaturated hydrocarbon group or a carbalkoxy group. They may be obtained by reacting an amino-triazole of the above formula, or a tautomeric form thereof, or a salt thereof, with a compound of the general formula or a salt thereof in which Hlg is a halogen atom, e.g. Cl or Br. Suitable salts of the amino-triazole are the hydrochloric acid and sulphuric acid salts and the bisulphate. The reaction is preferably carried out in the presence of a hydrogen halide binding agent, e.g. a primary, secondary, or tertiary amine, a metal compound, e.g. a metal oxide, hydroxide, carbonate, bicarbonate, alcoholate, or carboxylate, or ammonia or an ammonium compound, e.g. ammonium carbonate or acetate. An excess of the aminotriazole may also be used as acid-binding agent. A solvent may also be present and several suitable solvents are specified including hydrocarbons, aliphatic ethers and ketones, tertiary amines, acetonitrile, ethyl acetate, ethyl formate, nitrobenzene, carbon tetrachloride, and dimethylformamide. Examples are given for the production of compounds in which R1, R2, R3 and R4 are each methyl, X is oxygen and R5 is H, CH3, C2H5, (CH3)2CH, n-pentyl, heptyl, undecyl, phenyl, benzyl, styryl, p-chlorophenyl, p-methoxyphenyl, carbethoxy, carboisopropoxy, and carbo-n-pentoxy, respectively; R1, R2, R3 and R4 are each methyl, X is sulphur, and R5 is H or n-pentyl, and R1, R2, R3 and R4 ar each ethyl, X is oxygen and R5 is H or n-pentyl. Other R5 radicals mentioned are carboxyalkyl, isobutyl, and n-hexyl. The products have pesticidal properties (see Group VI). The amino-triazole starting materials may be obtained by reacting an amino-guanidine salt, e.g. the nitrate, bisulphate or sulphate with a carboxylic acid R5COOH or its acid halide and the preparation by this method of the aminotriazoles in which R5 is heptyl, undecyl, benzyl and styryl, respectively, is described. The preparation of starting compounds in which R5 is a carbo-n-pentoxy and a carbo-isopropoxy group by treating the corresponding free carboxylic acid (R5=COOH) with n-pentanol and isopropanol, respectively, in the presence of dry HCl gas is also described.ALSO:A pesticidal composition comprises as active ingredient a compound which is a derivative of an amino-triazole of the general formula or of a tautomeric form thereof, in which derivative the phosphorus atom is bound to one of the nitrogen atoms of the triazol ring and in which R1, R2, R3 and R4 designate aliphatic hydrocarbon radicals, X is oxygen or sulphur, and R5 is a hydrogen atom, an alkyl, cycloalkyl, aryl or aralkyl group, or such group containing one or more substituents, or is an olefinically unsaturated hydrocarbon group or a carbalkoxy group (see Group IV (b)), said compound being dissolved or dispersed in or mixed with a liquid or solid carrier material, if desired with the addition of a surface-active substance, dispersion agent and/or adhesive. The active ingredient is effective against various fungi and insects and the composition may be in the form of a water-miscible oil, wettable powder or dust powder. Specified liquid diluents are xylene, toluene, dioxane, petroleum distillates rich in aromatic compounds, e.g. solvent naphtha, distilled tar oil, tetrahydronaphthalene, cyclohexane and mixtures of such liquids. Specified solid carriers include alumina, kaolin, talcum chalk, diatomaceous earth, infusorial earth, wood flour, tobacco dust and ground coconut shells.