Patent GB-947485-A (GB)
Title: Improvements in or relating to heterocyclic amidophosphate compounds and combating noxious organisms thereby
IPC: C07F9/6512
Filed: 1960-03-07
Abstract: The invention comprises compounds of the general formula: <FORM:0947485/C2/1> in which Q is the residue of a compound QH comprising a heterocyclic nucleus of aromatic character which nucleus contains a nitrogen atom and from one to three further hetero atoms, X is oxygen or sulphur, R1, R2, R3 and R4 each represent a C1-C5 alkyl group and X is bound to a carbon atom of the heterocyclic nucleus of Q.  The hetero atoms in the residue Q may be O, S, or N and the heterocyclic nucleus may form part of a condensed ring system with a benzene nucleus.  The compound QH may be a substituted or unsubstituted 1, 2, 4-triazole, a thiazole, indazole, 1, 2, 4-thiadiazole, pyrimidine, pyrazole, benzoxazole or benzthiazole and especially advantageous compounds are derivatives of alkyl - pyrazole -5- ones and pyrazole -5- ones substituted by one or more phenyl or chlorphenyl groups.  An alkyl or phenyl group may be linked to a ring nitrogen atom in the pyrazole -5- one ring.  The compounds may be obtained by reacting a compound Q-X-H, preferably in the presence of a halogen hydracid-binding agent or a compound Q-X-M, in which Q and X are as defined above, X being linked to a C-atom of the heterocyclic nucleus of Q and M is a metal atom, preferably sodium or potassium with a compound of the formula: <FORM:0947485/C2/2> in which Hlg represents a halogen, preferably chlorine, atom or the group N(R1)(R2) and Y2 is halogen, preferably chlorine or the group N(R3)(R4) and reacting the resulting product if Y1 and/or Y2 represent a halogen atom or atoms with dimethylamine or other appropriate dialkylamine.  The halogen hydracid binding agent is suitably an amine especially a tertiary amine including pyridine and its homologues, or an alkaline compound or weak acid salt of Na, K, Mg, Ba, Ca or Zn, especially sodium or potassium alcoholate. The reaction in preferably carried out in the presence of a solvent, e.g. an aliphatic or aromatic hydrocarbon, an aliphatic ether, a tertiary amine (including pyridine), a nitrile, a ketone, ester, nitrobenzene or carbon tetrachloride.  The reaction is preferably effected at elevated temperature, e.g. between 50 DEG  and 120 DEG C.  The heterocyclic nucleus of Q may be substituted by alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, alkylamino, dialkylamino, arylamino, diarylamino, acylamino, alkoxy, alkylmercapto or amino groups or by halogen atoms, especially chlorine.  R1, R2, R3 and R4 are preferably methyl groups.  Several examples are given and the products have pesticidal properties (see Division A5). Specification 940,921 is referred to.ALSO:A pesticidal and herbicidal composition comprises at least one active compound of the formula <FORM:0947485/A5-A6/1> in which Q is the residue of a compound QH comprising a heterocyclic nucleus of aromatic character which nucleus contains a nitrogen atom and from one to three further hetero atoms, e.g. O, S, or N, X is oxygen or sulphur, R1, R2, R3 and R4 each represent a C1-C5 alkyl group, preferably methyl, and X is bound to a carbon atom of the heterocyclic nucleus of Q (see Division C2) said active compound being mixed with or suspended or dissolved in a solid or liquid diluent.  The compound QH may be a substituted or unsubstituted 1,2,4-triazole, a thiazole, indazole, 1,2,4-thiadiazole, pyrimidine, pyrazole, benzoxazole or benzthiazole and especially an alkyl-pyrazole-5-one or a pyrazole-5-one substituted by one or more phenyl or chlorophenyl groups.  An alkyl or phenyl group may be linked to a nitrogen atom in the 5-pyrazole-5-one ring.  The heterocyclic nucleus of Q may be substituted by alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, aralkyl, amino, alkylamino, dialkylamino, arylamino, diarylamino, acylamino, alkoxy, alkylmercapto or amino groups or by halogen atoms, especially chlorine.  The composition may contain a dispersion agent, emulsifier and/or wetting agent.  The composition may be in the form of a water-miscible oil suitable solvents being xylene, toluene, dioxane, solvent naphtha, distilled tar oil, tetrahydronaphthalene cyclohexane and mixtures of such liquids. Specified solid diluents are pipe clay, diatomaceous earth, kaolin, dolomite, talcum, gypsum, clay, bentonite, attapulgite, kieselguhr, celite, wood meal, tobacco dust and ground coconut shells and the composition may suitably be in the form of a wettable powder or dust.  Specification 940,921 is referred to.