Patent GB-1233742-A (GB)
IPC: C07F7/22
Filed: 1968-05-17
Abstract: 1,233,742. Isothiazole derivatives; organotin compounds. ROHM & HAAS CO. 17 May, 1968 [21 June, 1967], No. 23687/68. Headings C2C and C2J. [Also in Division A5] Novel isothiazole derivatives having the Formula I or II wherein Z is H, C 1-4  alkyl, halogen or cyano; Z<SP>1</SP> is C 1-4  alkylthio, aralkylthio of up to 8 carbon atoms, C 1-4  alkylsulphinyl, aralkylsulphinyl of up to 8 carbon atoms, C 1-4  alkylsulphonyl, or aralkylsulphonyl of up to 8 carbon atoms when Z is cyano; Z<SP>1</SP> is H, C 1-4  alkyl, aralkyl of up to 8 carbon atoms, halogen or C 1-4  haloalkyl when Z is H, C 1-4  alkyl or halogen. X in Formula I is di (C 1-4 ) alkyl phosphoryl; di (C 1-4 )-alkyl thionophosphoryl; di (C 1-4 ) alkyl dithiophosphoryl; di (C 1-4 ) alkyl dithiothionophosphoryl; di (C 1-4 ) alkoxyphosphino; di (C 1-4 ) alkyldithiophosphino; tri (C 1-4 ) alkyltin; triphenyltin; alkylsulphenyl of 1 to 12 carbon atoms; halo-substituted C 1-4  alkylsulphenyl; C 1-4  alkylsulphonyl; phenylsulphonyl; C 1-4  alkyl - or halo - substituted phenylsulphonyl; the group of the formula -C=CH-R, wherein R is CN, CO 2 H, CONH 2 , CONHR<SP>II</SP>, CON(R<SP>II</SP>) 2 , or -COOR<SP>II</SP> wherein R<SP>II</SP> is C 1-4  alkyl; the group wherein R<SP>III</SP> is di(C 1-4 ) alkylamino, C 1-4 -alkylthio, C 1-4  alkoxy, phenoxy or thiophenoxy; the group wherein R<SP>IV</SP> is alkyl of 1 to 12 carbon atoms, alkoxy of 1 to 6 carbon atoms, phenoxy, thiophenoxy, C 1-4  alkylthio, di (C 1-4 ) alkylamino, an aryl group of the formula wherein each of the R<SP>V</SP> groups which may be the same or different is C 1-4  alkyl, C 1-4  alkoxy, halogen or nitro and n is zero or an integer from 1 to 3; or the difunctional group having the formula where Y in Formula II is a methylene or polymethylene chain of up to 10 carbon atoms, phenylene or a C 1-4  alkyl- or halo-substituted phenylene: Z<SP>11</SP> and Z<SP>111</SP> in Formula II are as defined for Z and Z<SP>1</SP> respectively in Formula I. The dotted lines in Formulµ I and II represent the two positions to which X or may be attached. Compounds of Formula I are prepared by reacting a compound of Formula VII wherein Z and Z<SP>1</SP> are as defined above, with an active halogen of the formula XZ<SP>1111</SP> wherein X is as defined above and Z<SP>1111</SP> is a halogen atom, and where X is -CH=CH-R where R is as defined above compounds of Formula I may also be prepared by reacting a compound of the Formula VII with a compound of the formula CH=CH-R. The former process may be carried out in the presence of an inert organic solvent or an acid scavenger. The latter process may be carried out in the presence of a basic catalyst such as a quaternary ammonium hydroxide or a trialkylamine such as triethylamine or pyridine. Compounds of Formula II are prepared by reacting a compound of the Formula VII wherein Z and Z<SP>1</SP> are as defined above, with an active halogen of the formula wherein Y is as defined above and Z<SP>1111</SP> is a halogen atom. This process may be carried out in the presence of an inert organic solvent or an acid scavenger. Substituted 3-hydroxyisothiazoles are disclosed and claimed in Specification 1,224,663.