Patent GB-937361-A (GB)
Title: New phosphorothiolic esters and pesticidal compositions comprising them
Inventor: PIANKA MAX
IPC: C07F9/165
Filed: 1959-01-20
Abstract: The invention comprises compounds of the general formula:- <FORM:0937361/IV(a)/1> in which R and R1 may be the same or different and each is a C1-C4 alkyl group, Z is a sulphur atom or an SO2 group, and R2 is one of the following groups:-(1) a substituted thiocarbamoyl group, viz -C(S).  NR3R4 in which R3 is a hydrogen atom or an alkyl or cycloalkyl group and R4 is an alkyl or cycloalkyl group, (2) an alkoxy- or cycloalkoxy-thiocarbonyl group, viz C(S)OR5 wherein R5 is an alkyl or cycloalkyl group, (3) an alkyl-thioalkyl or furfuryl group, or (4) an aryl or substituted aryl group, with the proviso that when Z is an SO2 group R2 is not (1) or (2), and acid addition salts, e.g. hydrochlorides or hydrogen oxalates, of such compounds containing basic groups.  When R2 is an aryl or substituted aryl group it may be phenyl or naphthyl or either of these groups substituted by one or more chloro or nitro groups.  The compounds may be obtained by condensing a compound of the formula (RO)2P(O).S.X wherein R and R1 are as defined above and X is Cl, Br or I with a compound of the formula M.Z.R2 wherein R2 and Z are as defined above and M is hydrogen, an alkali metal or ammonium, if desired in solution or suspension in a solvent or diluent.  The reaction is preferably carried out at room temperature but heat may be applied if necessary.  When M is hydrogen an acid binding agent may be used. Examples are given and the products have pesticidal properties (see Group VI).  On heating or on standing the products may be converted from the =P(O)S- form to the =P(S)O- form.  According to the Provisional Specification the radical R2 may be an alkyl radical or an alkyl radical substituted by chlorine, nitro, phenyl, chlorophenyl, nitrophenyl, naphthyl, furyl or thiophene radical or may be an alkoxyalkyl group, or a heterocyclic group such as thiazoline or benzthiazoline.ALSO:A pesticidal composition comprises a carrier or diluent and as active ingredient a compound having the formula <FORM:0937361/VI/1> in which R and R1 are the same or different and are C1-C4 alkyl groups, Z is a sulphur atom or an SO2 group, and R2 is one of the following groups: (1) a substituted thiocarbamoyl group -C(S)NR3R4, in which R3 is a hydrogen atom or an alkyl or cycloalkyl group and R4 is an alkyl or cycloalkyl group, (2) an alkoxy or cycloalkoxy thiocarbonyl group -C(S)OR5 where R5 is an alkyl or cycloalkyl group, (3) an alkylthioalkyl or furfuryl group, or (4) an aryl or substituted aryl group with the proviso that where Z is an SO2 group R2 is not (1) or (2), or an acid addition salt, e.g. hydrochloride or hydrogen oxalate, of such compounds containing basic groups (see Group IV (b)).  The composition may be a solid or liquid composition and may include a wetting, dispersing or emulsifying agent.  It may be in the form of an aerosol, a paste, dust, wettable powder, granulate or pellet, or a thermal fumigating mixture and the solid preparations may include diluents such as clays, and binding and/or adhesive agents.  Other insecticides and/or fungicides may also be present.  When R2 is an aryl group it may be phenyl or naphthyl which may be substituted by one or more chloro or nitro groups.  According to the Provisional Specification the radical R2 in the active ingredient may be an alkyl radical or an alkyl radical substituted by chlorine, nitro, phenyl, chlorophenyl, nitrophenyl, naphthyl, furyl or thiophene radical or may be an alkoxyalkyl group or a heterocyclic group such as thiazoline or benzthiazoline.