Patent GB-783281-A (GB)
Title: New pesticidal basic esters of phosphorothiolothionic acid
Inventor: GHOSH RANAJIT
IPC: C07F9/165
Filed: 1954-08-10
Abstract: The invention comprises phosphorothiolothionic esters of the formula: S = P(OR1)(OR2)-S-LX wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical in which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom.  The compounds are prepared (1) by reacting an alkali metal salt of a dialkyl phosphorothiolothionate of the formula: S = P(OR1)(OR2)-S Met wherein Met represents an alkali metal, with an aminoalkyl derivative of formula YLX1, wherein Y represents halogen and X1 represents a secondary aliphatic or heterocyclic amino radical not attached to the same carbon atom as Y; and (2) by reacting a dialkyl phosphorohalidothionate of the formula: S = P(OR1)(OR2)-Z wherein Z represents halogen, with an aminoalkyl mercaptan of the formula MetSLX1, X1 not being attached to the same carbon atom as the mercapto group.  The examples describe the preparation of o:o1-diethyl S-b -diethylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 1 - di - n - propylaminoprop - 2 - yl phosphorothiolothionate, o:o1 - diethyl S - 1 - diethylamino - 3 - ethoxy - prop - 2 - yl phosphorothiolothionate, o:o1 - diethyl S - b - di-n - propylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 1 - diethylaminoprop - 2 - yl phosphorothiolothionate o:o1 - diethyl S - b -di - n - butylaminoethyl phosphorothiolothionate, o:o1 - diethyl S - 3 - diethylaminopropyl phosphorothiolothionate, o:o1 - diethyl S - b -piperidinoethyl phosphorothiolothionate, o:o1-di - n - propyl S - b  - diethylaminoethyl phosphorothiolothionate, o:o1 - di - n - propyl S-b  - piperidinoethyl phosphorothiolothionate, o - ethyl o1 - n - propyl S - b  - diethylaminoethyl phosphorothiolothionate, o:o1 - diethyl S-[1 - di - n - propylamino - 3 - ethylthio] - prop-2 - yl phosphorothiolothionate and o:o1 - diisopropyl S - b  - dimethylaminoethyl phosphorothiolothionate.  3 - Ethylthio - 1 - di - n - propylamino - propane - 2 - ol is prepared by condensing 1 - chloro - 3 - ethylthiopropan - 2 - ol with di - n-propylamine.  2 - Chloro - 1 - di - n - propylamino - 3 - ethylthiopropane is prepared by reacting thionyl chloride with 3-ethylthio-1-di-n-propylaminopropane-2-ol.  Reference has been directed by the Comptroller to Specification 740,563.ALSO:A combined plant nutrient and pesticidal composition comprises a phosphorothiolothionic ester of the formula: S = P(OR1)(OR2)-S-LX wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical in which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom, together with a plant nutrient and, if desired, a solid or liquid carrier and/or an auxiliary agent. Specified plant nutrients are urea and magnesium sulphate. Specified carriers are water, non-phytocidal organic solvents, talc, kieselguhr, bentonite, other colloidal clays and powdered chalk. Specified auxiliary agents are spindle oil, glycerol, wool fat, sodium dinaphthylmethane disulphonate, sodium lauryl sulphate, glue and resin.  Reference has been directed by the Comptroller to Specification 740,563 [Group VI].ALSO:A pesticidal composition comprises a phosphorothiolothianic ester of the formula S=P(OR1)(OR2)-S-LX, wherein R1 and R2 are alkyl radicals, L is a saturated aliphatic hydrocarbon radical n which the carbon atoms may be interrupted by an oxygen atom, a sulphur atom or an N-Alkyl substituent, and X represents a secondary aliphatic or heterocyclic amino radical attached to L through the amine nitrogen atom, said nitrogen atom not being attached to the same carbon atom as the sulphur atom linking L with the phosphorus atom, together with a solid or liquid carrier and, if desired, an auxiliary agent and/or a plant nutrient.  Specified carriers are water, non-phytocidal organic solvents, talc, kieselguhr, bentonite, other colloidal clays and powdered chalk.  Specified auxiliary agents are spindle oil, glycerol, wool fat, sodium dinaphthylmethane disulphonate, sodium lauryl sulphate, glue and resin.  Specified plant nutrients are urea and magnesium sulphate.  Reference has been directed by the Comptroller to Specification 740,563.