Patent GB-1033911-A (GB)
Title: Organophosphorus derivatives of cyclic sulfones and intermediates therefor
IPC: A01N57/16
Filed: 1963-01-01
Abstract: The invention comprises cyclic sulphones of the general formula:- <FORM:1033911/C2/1> wherein R is an alkyl radical, Q is O or S, and Z is alkylmercapto, substituted alkyl-mercapto, arylmercapto, or substituted arylmercapto, or Q is oxygen and Z is alkoxy, substituted alkoxy, aryloxy or substituted aryloxy.  The alkyl radicals including those forming part of Z may be branched or unbranched C1-C8 alkyl radicals preferably methyl, ethyl, propyl or isopropyl and examples of substituted alkyl or aryl-mercapto or -oxy radicals are nitroarylmercapto, chlorinated alkylmercapto, chlorinated arylmercapto, nitroaryloxy, chlorinated alkoxy and chlorinated aryloxy.  The compounds in which Z is an alkyl- or aryl-mercapto (either of which may be substituted) may be obtained by reacting 3-sulpholene-(2,5-dihydrothiophene -1,1-dioxide) with a sulphenyl halide VX wherein V is alkyl- or aryl-mercapto (either of which may be substituted) and X is halogen and then treating the resulting 3-halo-4-(alkyl-or aryl-mercapto) substituted heterocyclic compound with a compound MSP(Q)(OR)2 in which M is a cation, e.g. a metal or ammonium, and R is alkyl. Compounds in which Q is oxygen may be obtained by reacting 3-sulpholene with a dialkoxy-phosphinyl sulphenyl halide (RO)2P(O)SX wherein X is halogen, preferably Cl, to form a 4-halo-3-dialkoxyphosphinylthiotetrahydrothienyl - 1,1 - dioxide and then reacting the latter with a compound ZM wherein M is a cation, e.g. a metal or ammonium cation and Z is as defined above. An example of an intermediate formed in the first type of process is the compound 3-chloro-4 - (4 - nitrophenylmercapto) tetrahydrothiophene 1,1-dioxide and an example of an intermediate formed in the second process referred to is O,O - diethyl - S - (4 - chloro - 1,1 - dioxy-tetrahydro - 3 - thienyl) phosphorothioate and the invention also includes these specific compounds per se.  Each type of process can be carried out in the presence of a diluent, e.g. an inert aromatic or aliphatic hydrocarbon, a ketone or an alcohol and the reaction temperature may be from 0 DEG  to 200 DEG  C.  The compounds of the given general formula have pesticidal properties (see Division A5).  p-Nitrophenylsulphenyl chloride is obtained by treating bis-(p-nitrophenyl) disulphide in dry chloroform with gaseous chlorine.ALSO:A pesticidal composition contains as active ingredient a compound of the formula:- <FORM:1033911/A5-A6/1> wherein R is alkyl, Q is O or S and Z is alkylmercapto, substituted alkylmercapto, arylmercapto, or substituted aryl mercapto, or Q is oxygen and Z is alkoxy, substituted alkoxy, aryloxy or substituted aryloxy (see Division C2).  The active ingredient may be used in admixture with other pesticides, e.g. DDT (Trade Mark), methoxychlor, lindane, aldrin, endrin, DDD (Trade Mark), BHC, parathion, Malathion (Trade Mark), methyl parathion, lead and other metallic arsenates, rotenone, allethrin, pyrethrum, nicotine, summer oils, dormant oils, petroleum fractions and distillates, dinitroalkylphenols, chlordane, heptachlor, chlorinated terpenes, demeton, other organophosphates and thiophosphates, bis(pentachlorocyclopentadienyl), chlorinated aryl sulphonates, quinoxaline trithiocarbonates, chlorinated diarylsulphones, sulphur, dithiocarbamates and N-trichloromethylthio-4-cyclohexene-1, 2-carboxamide.  Substances having synergistic properties, e.g. organic thiocyanates, Phosdrin (Trade Mark) and [2-(3, 4-methylenedioxyphenoxy)-3, 6, 9-trioxaundecane] may also be present.  Solid or liquid carriers may be used and the composition which may contain a wetting agent, dispersing agent, suspending agent, or emulsifying agent may be in the form of a dust, powder, dispersion, suspension, solution or emulsion.