Patent GB-988974-A (GB)
Title: Substituted 3-trichloromethylthio-1,3,4-oxa(or thia)diazoles
IPC: C07D285/125
Filed: 1963-06-18
Abstract: The invention comprises compounds of formula <FORM:0988974/C2/1> where X and X1 may be the same or different, and may represent oxygen or sulphur, and R is hydrogen, an alkyl group which may be substituted by a halogen atom, a nitro or cyano group; an alkenyl group; an aliphatic hydrocarbon group interrupted by oxygen, sulphur, or a sulphoxyl or sulphonyl group; an alkylthio group; an alkoxycarbonyl group; a carbamoyl group which may be substituted e.g. by one or two alkyl groups; an aryl group which may be substituted; an aralkyl group containing 7-12 carbon atoms the aryl moiety of which may be substituted and the alkyl moiety separated may be from the aryl group by an oxygen or sulphur atom, or have its chain interrupted by an oxygen or sulphur atom or a sulphonyl or sulphoxyl group; a cycloalkyl or cycloalkyl-alkyl group; or a heterocyclic group which may be substituted. The term "substituted" when applied to the aryl or heterocyclic groups above indicates that the group may be substituted by one or more of the following:  chlorine atoms, nitro, cyano, alkyl, alkoxy, hydroxy or alkoxycarbonyl, the alkyl and alkoxy groups containing 1-4 carbon atoms. The compounds are prepared by reacting compounds of formula <FORM:0988974/C2/2> or an alkali metal derivative thereof, with perchloromethylmercaptan preferably in water or an inert organic solvent at a temperature of 0 DEG  to 50 DEG  C.  Condensing agents may be employed.  1,3,4-oxa (or thia) diazoles of the general Formula II above, are obtained by reacting compounds of formula CX,Cl2 with a hydrazide of formula R-CX-NH.NH2, X,X1, and R having the above significance.  5 - methylthio - 1,3,4 - thiadiazol - 2 - one is prepared by reacting dimethylcarbamoyl chloride with methyldithiocarbazinate.ALSO:Fungicidal compositions for agricultural use contain at least one of the compounds of formula <FORM:0988974/A5-A6/1> where X and X1 may be the same or different and may represent oxygen or sulphur, and R is hydrogen, an alkyl group which may be substituted by a halogen atom, a nitro or cyano group; an alkenyl group; an aliphatic hydrocarbon group interrupted by an oxygen, sulphur atom, or a sulphoxyl or sulphonyl group; an alkylthio group; an alkoxycarbonyl group; a carbamoyl group which may be substituted e.g. by one or two alkyl groups, an aryl group which may be substituted; an aralkyl group containing 7-12 carbon atoms the aryl moiety of which may be substituted and the alkyl moiety may be separated from the aryl group by an oxygen or sulphur atom, or have its chain interrupted by an oxygen or sulphur atom or a sulphonyl or sulphoxyl group; a cycloalkyl or cycloalkyl-alkyl group; or a heterocyclic group which may be substituted.  The term "substituted" when applied to the aryl or heterocyclic groups above indicates that the group may be substituted by one or more of each of the following: chlorine atoms and nitro, cyano, alkyl, alkoxy, hydroxy or alkoxycarbonyl groups, the alkyl and alkoxy groups having 1-4 carbon atoms.  The compositions preferably contain 0.005-90% by weight of the oxa (or thia) diazole in an inert solid or liquid diluent. Liquid compositions may be suspensions, emulsions, or solutions in organic or aqueous organic media e.g. aromatic hydrocarbons, or mineral or vegetable oils.  The compositions may also contain wetting, dispersing or emulsifying agents preferably of the non-ionic type.  Fertilizers may be mixed with the compositions.  Therapeutic compositions useful as fungicides and which may be administered orally or topically, contain as active ingredient compounds of the general formula above.  The composition may be in the form of a cream, ointment, powder, granule, tablet, pill, vaginal tablet or capsule.