Patent GB-851795-A (GB)
Title: Fungicidal compositions and compounds for use therein
Inventor: HACKMANN JOHANES THOMAS
IPC: C08G63/68
Filed: 1958-04-21
Abstract: Polyester polysulphides are made by reacting in an aqueous or aqueous alcoholic medium, an inorganic polysulphide M2 Sx where M is a hydrogen equivalent of ammonium, an alkali metal or an alkaline earth metal and x is 3 to 6, with [A] a compound XRX1 where X and X1 are the same or different halogens and R is a hydrocarbon group substituted by at least one esterified hydroxyl group, or with [B], a compound XRX1 where X and X1 are the same or different halogens and R is a hydrocarbon group substituted by at least one hydroxyl group, followed by reaction of the resultant polyhydroxy polysulphide with an esterifying agent to produce the corresponding polyester polysulphide.  Specified inorganic polysulphides are sodium pentasulphide, sodium tetrasulphide, calcium tetrasulphide and ammonium hexasulphide.  Specified compounds of the formula XRX1 are 1 :2-and 1 : 3-dichlorohydrin, 2 : 3 and 3: 4-dichloro-n-butanol, 2 : 3-, 2 : 4- and 3 : 4-dichlorobutane-2 : 3-diol, 4 : 5-dichloro-n-pentanol, 2 - 3:dichloro-1-methyl propanol, 1 : 4-dichlorobutane-2 : 3-diol and esters thereof. Specified fungicidally active acids from which the esterified hydroxyl groups of the compounds used in method [A] are derived and which are also used per se or in the form of acid chlorides, acid anhydrides and esters for esterifying the polyhydroxy sulphides made by method [B] include phosphoric, acrylic, crotonic, alkyl sulphonic, xanthic, dithiocarbamic, thiolcarboxylic, mono-, di- and tri-chloracetic, trichloromethyl, sulphonic, benzoic, chlorinated benzoic, nitrobenzoic, chloronitrobenzoic, cinnamic, 3-methoxy-4-hydroxy-cinnamic, 4- methoxy-3-hydroxycinnamic, 3 : 4-dyhydroxycinnamic, p-toluene sulphonic and dodecyl benzene sulphonic acid.  In Examples (I) to (IV), poly (2-hydroxypropylenetetrasulphide-1 : 3) made by reacting 1 : 3-dichlorohydrin with sodium tetrasulphide is esterified by reaction with:-(I) chloracetyl chloride, (II) 4-nitrobenzenesulphonyl chloride, (III) dichlorobenzenesulphonyl chloride and (IV) trichloromethyl sulphonyl chloride; whilst in Example (V) an aqueous suspension of poly (2-toluene-p-sulphonyloxy-propane-1 : 3-tetrasulphide) is made by reacting 2-toluene-p-sulphonyloxy-1 : 3-dichloropropane with sodium tetrasulphide.  The products of the invention are soluble in basic solvents e.g. pyridine and may be compounded with talc, clay, silica, fuller's earth or kieselguhr for agricultural and horticultural use.ALSO:A fungicidal composition comprises a polyester polysulphide (see Group IV(a)) and a carrier and/or a surface active agent. The carrier may be solid or liquid, specified solid carriers being finely divided talc, clay, silica, fuller's earth and kieselgulr, specified liquid carriers being basic solvents, e.g. pyridine and aqueous dispersants.  Specified surface active active agents which may also be dispersing agents are sodium, potassium or calcium lignin sulphonate or a polyaryl polysulphonate. Example VI describes the use of suspensions of poly (2-chloroacetoxypropane-1:3-tetrasulphide), poly (2-toluene-p-sulphonyloxypropane-1:3-tetrasulphide), poly (2-benzenesulphonyloxypropane-1:3-tetrasulphide), poly (2-p-nitrobenzenesulphonyloxypropane-1:3-tetrasulphide and poly (2-31:41-dichlorobenzenesulphonyloxypropane-1:3 -tetrasulphide made by dissolving the polymers in the minimum quantity of pyridine and adding said solutions to water.