http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1017983-A

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filingDate 1964-01-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1966-01-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1017983-A
titleOfInvention Pesticidal heterocyclic phosphorus acid esters
abstract The invention comprises esters of phosphorus acids, of formula <FORM:1017983/C2/1> wherein R and R1 are the same or different, C1 t C4 alkyl, halogenated C1 to C4 alkyl, C2 to C4 alkenyl, C1 to C4 alkoxy-substituted C2 to C4 alkenyl, C1 to C4 alkylmercapto-substituted C2 to C4 alkenyl, cycloalkyl, C1 to C4 alkoxy, aralkyl, or aryl; and R may also be C1 to C4 alkylamino, di-C1 to C4 alkyl amino, or di-C1 to C4 alkenyl amino; R11 is hydrogen, alkyl, phenyl, halogenated phenyl, nitro-substituted phenyl, C1 to C4 alkyl substituted-, or C1 to C4 alkoxy substituted-, or C1 to C4 alkylmercapto-or di-C1 to C4 alkylamino substituted phenyl or a 5- or 6-membered O, S, or N containing heterocycle; R111 is hydrogen, or alkyl, with the proviso that if R111 is alkyl, R11 must be alkyl; and X is O or S. The compounds are prepared by reacting the corresponding phosphorus acid halide with appropriate 2-hydroxy-1,3-thiazoles, suitably in organic solvent in the presence of an acid binding agent; suitable solvents are low molecular weight alkanols, ethers, ketones, or nitriles, or aliphatic or aromatic, optionally chlorinated hydrocarbons. Acid binding agents may be alkali metal carbonates or alcoholates, or tertiary amines; alternatively salts (e.g. alkali metal or ammonium) of the thiazoles may be used without an acid binding agent. Examples are given for many compounds of the invention; they are useful as insecticides (see Division A5) and also as plasticizers and lubricant additives.ALSO:Insecticidal compositions comprise an inert diluent or carrier, with esters of phosphorus acids of formula: <FORM:1017983/A5-A6/1> wherein R and R1 are the same or different C1 to C4 alkyl, halogenated C1 to C4 alkyl, C2 to C4 alkenyl, C1 to C4 alkoxy-substituted C2 to C4 alkenyl, C1 to C4 alkylmercapto substituted C2 to C4 alkenyl, cycloalkyl, C1 to C4 alkoxy, aralkyl or aryl; and R may also be C1 to C4 alkyl amino, di-C1 to C4 alkylamino, or di-C1 to C4 alkenyl amino; R is hydrogen, alkyl, phenyl, halogenated phenyl, nitro-substituted phenyl, C1 to C4 alkyl substituted, or C1 to C4 alkoxy substituted-, or C1 to C4 alkyl mercapto substituted-or di-C1 to C4 alkyl amino substituted-phenyl, or a S- or 6-membered O, S, or N containing heterocycle; R111 is hydrogen, or alkyl, with the proviso that if R111 is alkyl, R11 must, also be alkyl; and X is S or O. Suitable carriers are liquid or solid e.g. talc, chalk, bentonite, clay, water with an emulsifier, alcohols, ketones, or liquid hydrocarbons, and the compositions may contain other known fertilisers and/or insecticides. An example is given for a composition of: O, O-diethyl-thiono-phosphoric acid-0-[4-phenyl-thiazolyl-(2)-] ester, and also the corresponding 4-(3-nitrophenyl)-compound, with an equal weight of dimethylformamide, and 20% of a benzyl hydroxypolyglycol ether (referred to the weight of active ingredient) as emulsifier, the concentrate being appropriately diluted with water before use. The preparation of the esters is widely exemplified, (see Division C2).
priorityDate 1963-01-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 38.