Patent GB-967166-A (GB)
Title: N-trichloromethylmercapto-spirohydantoins and fungicidal compositions containing them
Inventor: CREMLYN RICHARD JAMES CAMPBELL
IPC: C07D235/02
Filed: 1959-11-10
Abstract: The invention comprises compounds of the formula <FORM:0967166/C1/1> where A together with the adjacent carbon atom constitutes a substituted or unsubstituted alicyclic ring of 5, 6 or 7 carbon atoms, and Z is hydrogen nitro or an acyl group; and their production by reacting ClS.CCl3 with an alkali metal salt of the corresponding N-unsubstituted hydantoin, e.g. in aqueous solution at 10-30 DEG C. The alicyclic ring may be cycloalkyl and may be substituted, e.g. with alkyl or carbalkoxy radicals, or may be fused to another ring, e.g. a cyclohexane or benzene ring. The compounds of the invention are fungicides (see Division A5).  The Provisional Specification refers generally to compounds as above in which either or both of the C=O groups may be replaced by C=S, and in which the alicyclic ring is replaced by groups R and R1 where R is alkyl, aryl or aralkyl and R1 is hydrogen, aryl or aralkyl; in addition to spiro hydantoins, the compounds 5-phenyl-5-methyl -5- p-methoxyphenyl -5- methyl-, 5-phenyl-, 5-hexyl- and 5-heptyl -N- trichloromethylthio-hydantoin are specified.ALSO:Alkyd resin paints contain as fungicidal ingredient a compound of formula <FORM:0967166/C3/1> where A together with the adjacent carbon atom constitutes a substituted or unsubstituted alicyclic ring of 5, 6 or 7 carbon atoms, and Z is hydrogen, nitro or an acyl group (see Division C2).  According to the Provisional Specification, either or both of the C=O groups may be replaced by C=S, and the alicyclic ring may be replaced by groups R and R1, where R is alkyl, aryl or aralkyl and R1 is hydrogen, aryl or aralkyl.ALSO:Fungicidal paints contain as fungicidal ingredient a compound of formula <FORM:0967166/C4-C5/1> where A together with the adjacent carbon atom constitutes a substituted or unsubstituted alicyclic ring of 5, 6 or 7 carbon atoms, and Z is hydrogen, nitro or an acyl group (see Division C2).  According to the Provisional Specification either or both of the C = O groups may be replaced by C = S, and the alicyclic ring may be replaced by groups R and R1, where R is alkyl, aryl or aralkyl and R1 is hydrogen, aryl or aralkyl.ALSO:To protect plants against attack by plant pathogens, the seed from which the plant is to be grown is treated with a hydantoin compound of the following formula or with a fungicidal composition containing it:  <FORM:0967166/A1-A3/1> where A together with the adjacent carbon atom constitutes a substituted or unsubstituted alicyclic ring of 5, 6 or 7 carbon atoms, and Z is hydrogen, nitro or an acyl group (see Divisions A5 and C2).  The composition may also comprise a diluent liquid such as water or a non-toxic organic solvent, or a powdered solid carrier such as talc, china clay, gypsum, basic slag, kieselguhr or bentonite.  According to the Provisional Specification, either or both of the C=O groups may be replaced by C=S, and the olicyclic ring may be replaced by groups R and R1, where R is alkyl, aryl or aralkyl and R1 is hydrogen, aryl or aralkyl.ALSO:Fungicidal compounds of the formula <FORM:0967166/A5-A6/1> where A together with the adjacent carbon atom constitutes a substituted or unsubstituted alicyclic ring of 5, 6 or 7 carbon atoms, and Z is hydrogen, nitro or an acyl group (see Division C2) are used, as such or in compositions, for (i) protecting a cellulosic material, such as timber and cotton cloth, against attack by fungi; and (ii) protecting plants against attack by plant pathogens by treatment of the plant foliage or mould in which the plant is to be grown.  Carriers for the active compounds may be solid or liquid, e.g. water, organic solvents, talc, china clay, gypsum, basic slag, kieselguhr and bentonite.  Wetting or dispersing agents may be present.  According to the Provisional Specification, either or both of the C = O groups may be replaced by C = S, and the alicyclic ring may be replaced by groups R and R1, where R is alkyl, aryl or aralkyl and R1 is hydrogen, aryl or aralkyl.