PRODUCTION OF 5,5-DISUBSTITUTED 3-OXO-PENT-4-ENOIC ACIDS, THEIR HALIDES, ESTERS, THIOESTERS AND AMIDES; AND THEIR USE IN ANTIFUNGAL AND ANTIBACTERIAL COMPOSITIONS

摘要

A process is described for the production of a compound having the formula: R<2>R<2>C=CHCOCH2COZ I wherein R<2> is fluorine, chlorine, or bromine; R<3> is hydrogen, fluorine, chlorine or bromine, or a group of formula -CR<4>R<5>R<6> wherein R<4>, R<5> and R<6> are fluorine, chlorine or bromine; and Z is -AY or X<1> wherein A is -O-, -S- or -NR<7> wherein R<7> is hydrogen, C1-10 - straight - or branch chain alkyl or C3-4 straight or branch chain alkenyl, Y is hydrogen, C 1-18-straight or branch chain alkyl optionally interrrupted by one to five oxygen atoms and optionally substituted by one to five chlorine or bromine atoms, or by a group having the formula -OR<8> or the formula -CO2R<9> wherein R<8> is hydrogen, C3-12-cycloalkyl, straight- or branch chain C3-18-alkenyl, C6-10-aryl or C7-13-aralkyl and R<9> is hydrogen, C1-18-straight- or branch chain alkyl or straight- or branch chain C3-18-alkenyl, or Y is C3-18 straight or branch chain alkenyl, C3-18 straight- or branch chain alkynyl, C3-12-cycloalkyl, C7-13-aralkyl, or C6-10- aryl which is optionally substituted by one to three C1-9 straigth- or branch chain alkyl, halogen, nitro, CF3, or SO3H, or groups -OR<1><0> wherein R<1><0> is hydrogen or C1-4 straight or branch chain alkyl, provided that the total number of carbon atoms in the group -AY is from 0 to 20; or R<7> and Y together may form a C2-7 polymethylene chain optionally substituted by one or two C1-4 alkyl groups and optionally interrupted by -O-, -S- or NR<1><1> groups wherein R<1><1> is C1-4 straight or branch chain alkyl; and X<1> is C1 or Br; comprising (a) reacting, optionally in the presence of a solvent and an inorganic or organic acid - binding agent, a compound having the formula II: wherein R<2> and R<3> have their previous significance; R<1> is fluorine, chlorine or bromine; and X is chlorine, bromine or iodine with the proviso that, when X is chlorine, none of R<1>, R<2>, R<3>, R<4>, R<5> and R<6> can be bromine; with a compound of formula H-Z III wherein Z has its previous significance: and (b) when Z is -AY and -AY is -OH, the product of step a) is optionally reacted with a compound IV capable of converting a carboxyl group into the corresponding carboxylic acid chloride or -bromide, thereby producing a compound of formula I wherein Z is- X<1> as well as the use of the compounds of formula I in antifungal and antibacterial compositions.