Patent GB-1061472-A (GB)
Title: Bicyclic sulphur-containing organic compounds, their preparation and use
IPC: C07F9/6561
Filed: 1964-02-06
Abstract: The invention comprises (a) substituted 9, thiabicyclononanes having a [4,2,1] or [3,3,1] ring system, possessing n chlorine substituents, wherein n is 0 or an integer from 1 to 12, having 0, 1 or 2 oxygen atoms bonded to the 9 sulphur atom and having 1 or 2 substituents X and X1 located b  and b 1 respectively with respect to the 9 sulphur atom, each substituent having one of the following:  (1) a halogen atom;  (2) a radical of formula RZ wherein R is a hydrogen atom or a monovalent radical selected from "hydrocarbyl" and acyl, and Z is oxygen or sulphur;  (3) a radical of the formula NR1R2(R3)n <FORM:1061472/C2/1> wherein R1 and R2 are each a hydrogen atom or an acyl or "hydrocarbyl" radical or R1 may be a 9-thiabicyclo-[4,2,1] or [3,3,1]-nonyl radical or R1 and R2 may together with N form a heterocycle, R3 is a hydrogen atom or a "hydrocarbyl" radical, n is 0 or 1, n being 0 when either R1 or R2 is acyl, n1 is 0 when N is tertiary and 1 when N is quaternary, and Y is an anion of valence V; (4) a carboxyl radical or a salt, nitrile, amide, ester, or acid halide thereof;  (5) -N=C=S;  (6) a "hydrocarbyl" radical; (b) substituted 9-thiabicyclonanes as in (a) above wherein n is from 1 to 12 and neither X nor X1 is chlorine but wherein there are 1 to 12 identical substituents X11 in lieu of any of the chlorine atoms, X11 having the same meaning as X and X1 except chlorine; and (c) N-cyclohexylimino-9 -thiabicyclononane (see Example 15) and 10-aza - 9 - thiabicyclodecane (see Example 16). The term "hydrocarbyl" is defined as being the radical obtained on removal of one hydrogen atom from a hydrocarbon and such radical substituted by non-interfering groups.  The compounds of the invention are prepared by various methods from b ,b 1 - dichloro - 9 - thiabicyclononane, which compound is obtained by contacting a cyclooctadiene at -40 DEG  to 150 DEG  C. with a sulphur chloride.ALSO:Biocidal compositions comprise a compound which is either (a) a substituted 9-thiabicyclononane having a [4,2,1] or [3,3,1] ring system, possessing n chlorine substituents, wherein n is 0 or an integer from 1 to 12, having 0, 1 or 2 oxygen atoms bonded to the 9 sulphur atom and having 1 or 2 substituents X and X\sv located b  and b \sv respectively with respect to the 9-sulphur atom, each substituent being one of the following:  (1) a halogen atom;  (2) a radical of formula RZ wherein R is a hydrogen atom or a monovalent "hydrocarbyl" or acyl radical, and Z is oxygen or sulphur;  (3) a radical of the formula NR1R2(R3)n 7(n\sv/v) wherein R1 and R2 are each a hydrogen atom or an acyl or "hydrocarbyl" radical or R1 may be a 9-thialicyclo-[4,2,1] or [3,3,1]-nonyl radical or R1 and R2 may together with N form a heterocycle, R3 is a hydrogen atom or a "hydrocarbyl" radical, n is 0 or 1, n being 0 when either R1 or R2 is acyl, n1 is 0 when N is tertiary and 1 when N is quaternary, and 7 is an anion of valence v;  (4) a carboxyl radical or a salt, nitrile, amide, ester, or acid halide thereof;  (5) -N=C=S;  (6) a "hydrocarbyl" radical; or (b) a substituted 9-thiabicyclononane as in (a) above wherein n is from 1 to 12 and neither X nor X1 is chlorine but wherein there are 1 to 12 identical substituents X11 in lieu of any of the chlorine atoms, X11 having the same meaning as X and X1 except chlorine, together with a diluent or carrier therefor.  The biocidal compositions may be aqueous dispersions, aqueous emulsions, wettable powders, organic solutions or dusts and may contain other pesticides or insecticides or synergists, for example, piperaryl butoxide.  The solid formulations may also contain surface active agents, sticking agents, stabilizing agents or binders.