Patent GB-758600-A (GB)
Title: Improvements relating to heterocyclic monothiocarbonic acid esters, and compositions containing same
IPC: C07D263/58
Filed: 1954-06-18
Abstract: The invention comprises esters of heterocyclic monothiocarbonic acids of the formula <FORM:0758600/IV(a)/1> where X represents O, S, NH, or N-R1 (R1 being an alkyl radical of 1 to 5 carbon atoms), Y and Y1 may be hydrogen or halogen atoms or alkyl or alkoxy groups of 1 to 3 carbon atoms, or Y and Y1 may together form a fused benzene ring, Y11 is hydrogen or halogen and R is an alkyl radical of 1 to 5 carbon atoms.  Examples describe the preparation of monothiocarbonic acid-S-benzoxazolyl-(2)-O-methyl ester; monothiocarbonic acid-S-5-chlorobenzoxazolyl-(2)-O-methyl ester; monothiocarbonic acid-S-benzthiazolyl - (2) - O - methyl ester and monothiocarbonic acid - S - 5 - methylbenzthiazolyl - (2)-O-methyl ester; other specified products obtained according to the invention include the ethyl and n-propyl esters of S-benzoxazolyl-(2)-thiocarbonic acid; the methyl esters of 5 : 7-dichloro - S - benzoxazolyl - (2) -, 4 : 5 : 7 - trichloro - S - benzoxazolyl - (2) -, 5 - methyl - S-benzoxazolyl - (2) -, 5 - chloro - 7 - methyl - S-benzoxazolyl - (2) -, 5 - methoxy - S - benzoxazolyl - (2) -, S - 11 : 21 : 4 : 5 - naphthoxazolyl -(2)-, 5 - chloro - S - benzthiazolyl - (2) -, 4 - methoxy-S - benzthiazolyl -(2) -, S - 11 : 21 : 4 : 5 - naphthothiazolyl -(2) -, S - benzimidazolyl - (2) - and 1 - methyl - S - benzimidazolyl -(2) -, thiocarbonic acids; the ethyl ester of S - benzthiazolyl-(2)-thiocarbonic acid and the n-butyl ester of 5-methyl-S-benzthiazolyl-(2)-thiocarbonic acid.ALSO:Compositions for the control of fungi comprise compounds of the general formula: <FORM:0758600/VI/1> (see Group IV(b)) wherein X represents O, S, NH or N-R1, Y and Y1 are hydrogen, halogen or lower alkyl or alkoxy groups having 1-3 carbon atoms on Y and Y1 together form a fused benzene ring, Y11 represents hydrogen or halogen and R and R1 are alkyl groups of 1-5 carbon atoms, in combination with a carrier or diluent.  Suitable carriers comprise solid pulverulent carriers such as talcum, kaolin, bole, bentonite, chalk, or ground limestone, which may be made suspendable in water by the addition of wetting and dispersing agents.  The active substances can also be dispersed in water or organic solvents such as chlorinated hydrocarbons, e.g. trichloroethylene or petroleum fractions with the addition of auxiliary solvents such as acetone or higher ketones, dispersion being effected by the aid of emulsifiers.  The active substances may also be dispersed as aerosols or smokes.  The products are suitable for the protection of plants or parts thereof such as bulbs and tubers and also other organic materials such as wood, textiles, fur and leather.  In examples (6) mono-thiocarbonic acid-S- (5-chlorobenzexazolyl-(2))-O-methyl ester is mixed with kaolin or chalk and wetting or dispersing agents such as sulphite waste liquor plus ethylene oxide-alkyl phenol condensates to give a concentrate which is mixed with water to form a fungicidal spraying agent and (7) monothiocarbonic acid-S-benzthiazolyl-(2)-O-methyl ester is mixed with xylene and a condensation product of ethylene oxide itself or with an alkyl phenol to give a concentrate which may be used for preparing emulsions.  Many thiocarbonic esters of the general formula given are specified and the fungicidal activities of acetone solutions thereof are listed.