GB1037779A - Diazadiphosphetidine derivatives - Google Patents

Abstract

The invention comprises tetrakis (tert. alkyl), 1,3,2,4-diazadiphosphetidines and the corresponding diazadiphosphetidinium salts, of formula <FORM:1037779/C2/1> and <FORM:1037779/C2/2> wherein tert. alkyl is C4 to C11 tertiary alkyl; R is an organic group, and X is an anion. Preferred R groups are C1 to C4 alkyl, C2 to C5 alkoxy-methyl, or benzyl, which may be substituted by one or two alkyl groups, providing the total number of carbon atoms of the alkyl groups is 1 to 13; preferred anions are bromide, chloride, or iodide. The diazadiphosphetidines may be prepared by reacting at least two equivalents of a tertiary-alkylamine with PCl3, between about - 20 DEG C. and 100 DEG C., in the presence of an acid acceptor (e.g. excess tert-alkylamine, tertiary amines, or an inorganic base), preferably in an inert anhydrous solvent. The tertiary-alkylamines are preferably of formula CnH2n + 1.C(CH3)2.NH2 where n is 1 to 8. The diazediphosphetidinium salts are prepared by reacting the diazadiphosphetidine compounds with a quaternizing agent, preferably a reactive organic halide, if necessary in an inert anhydrous solvent, at temperatures of 20 DEG -100 DEG C. Preferred quaternizing agents are C1 to C4 alkyl halides; alkoxy halides where the alkoxy group is C1 to C4; and benzyl, alkyl benzyl, or dialkyl benzyl halides, where the alkyl groups have a total of 1 to 13 carbon atoms. Salts other than halides are suitably prepared from the halides by e.g. double decomposition with sodium salts of p-toluenesulphonate, methanosulphonate, lignosulphonate, acetate, or ferrocyanide. Examples are given for preparation of the tert. octyl-, tert. butyl-, and tert nonyl-diazadiphosphetidines and the corresponding phosphetidinium salts with methyl iodide and methyl chloride; and for the methoxy methyl chloride salt and dodecyl benzyl iodide salt from tert. octyl-diazadiphosphetidine. The phosphetidinium salts are used in fungicidal and algaecidal compositions (see Divisions A5-A6).ALSO:Biocidal compositions, especially useful as fungicides and algaecides, comprise tetrakis-(tert. alkyl)-1, 3, 2, 4-diazadiphosphetidinium salts, of formula <FORM:1037779/A5-A6/1> wherein R is an organic group, alkyl tert. is C4 to C11 tertiary alkyl, and X is an anion, (see Division C2) together with a diluent, which is either a solid or a liquid containing a surfactant. Preferred groups for R are C1 to C4 alkyl, C2 to C5 alkoxymethyl, or benzyl which may be substituted by one or two alkyl groups of a total of not more than 13 carbon atoms; preferred anions are chloride, bromide, and iodide. Suitable compositions include emulsifiable concentrates, wettable powders, dusts, granules, aerosols, and flowable emulsion concentrates. Compositions described are: emulsifiable concentrates of 10-25% by weight of active ingredient in solution in organic solvent (e.g. xylene, alkylated naphthalenes, pine oil, dimethyl phthalate) with an emulsifying agent; flowable emulsion, of up to 75% active ingredient, in water-immiscible inert solvent containing surfactant, with water added to produce a thick emulsion; wettable powders, comprising 20 to 50% active ingredient in a finely divided solid (e.g. clay, inorganic carbonate, or silicate), with wetting agents, dispersing agents, and/or other surfactants; dusts, containing 20 to 80% of active ingredient with finely divided organic or inorganic solids (e.g. botanical flour, silica, silicates, carbonates or clays) which may be diluted to 1 to 10% concentration before use.