Substituted phthalides and heterocyclic phthalides

A compound of formula I ##STR387## wherein ring system A a five membered heteroaromatic ring comprising oxygen, sulphur or nitrogen as heteroatom(s) which ring may be fused to a benzene ring or may comprise nitrogen as an additional heteroatom;

• R is cyano, formyl, CX.sub.1 X.sub.2 X.sub.3, a carboxyl group which may be in the form of the free acid or in ester or salt form, a thiocarboxyl group which may be in the form of the free acid or in ester form, a carbamoyl group or a mono- or di- substituted carbamoyl group, hydroxyalkyl, hydroxybenzyl, --CH.dbd.NOH, --CH.dbd.NO-lower alkyl, the group --CH.sub.2 --O--C(O)-- which bridges adjacent carbon atoms in ring A,
• Y.sub.1, and Y.sub.2 are attached to carbon atoms and are independently hydrogen, halogen, hydroxy, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylsulfonyloxy, dialkylsulfamoyloxy, alkylsulfonyl, alkylsulfinyl, dialkylcarbamoyloxy, alkylthio, alkenylthio or alkynylthio each of which may in turn be substituted by 1 to 6 halogen atoms;
• dialkoxymethyl, conjugated alkoxy, hydroxyalkyl, carboxyl, acyl, acylalkyl, acyloxy, acyloxyalkyl, trialkylsilyloxy, trialkylsilyl, cyano, nitro, amino or substituted amino, aminosulfonyl;
• cyclo-alkyl, aryl, aralkyl, aralkenyl, aralkynyl, aryloxy, aralkoxy, arylsulfonyl, arylsulfinyl, arylthio or aralkylthio, each of which may be substituted by one to three substituents selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, alkylthio, acyl, amino or substituted amino;
• a group ##STR388## wherein R' is hydrogen, lower alkyl, or lower alkoxy;
• or Y.sub.1 and R taken together on adjacent carbon atoms form a bridge having the formula ##STR389## wherein E is a 1 to 3 membered linking group with elements selected from methylene, substituted methylene, ##STR390## and oxygen;
• or Y.sub.1 and Y.sub.2 taken together on adjacent carbon atoms form a 3- to 5-membered bridge comprised of elements selected from methylene, substituted methylene, ##STR391## oxygen, and ##STR392## R.sub.1, R.sub.3 ' and R.sub.3 are independently hydrogen;
• halogen;
• alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, alkenylthio or alkynylthio, each of which may in turn be substituted by 1 to 6 halogen atoms;
• cycloalkyl, heterocycloalkoxy, aryloxy, aralkoxy or aralkylthio each of which may be substituted by 1 to 3 substituents selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, alkylthio, acyl, amino or substituted amino;
• aminoxy;
• substituted aminoxy;
• iminoxy;
• substituted iminoxy;
• amino;
• substituted amino;
• amido;
• substituted amido;
• alkylsulfonylmethyl;
• cyano;
• nitro;
• or ##STR393## wherein Y.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy or unsubstituted or substituted phenyl;
• R.sub.4 is as defined for Y.sub.1 except for hydrogen;
• X and Y each is independently hydrogen, hydroxy, halogen, cyano, alkyl, alkoxy, alkoxycarbonyl, alkoxycarbonyloxy, hydroxyalkyl, haloalkyl, acyl, acyloxy, carbamoyl, carbamoyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylsulfonyloxy;
• aryl, aryloxy, arylS(O)p, aralkyl, aralkoxy, aralkS(O)p, arylsulphonyloxy, each of which may in turn be substituted by 1 to 3 substituents selected from halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, nitro, cyano, alkylthio, acyl;
• amino, substituted amino or together represent .dbd.O, .dbd.S, .dbd.NH, .dbd.NOR.sub.12 or .dbd.CR.sub.13 R.sub.14 ;
• or
• X and R together may form a bridge having the formula --O--E--, ##STR394## wherein the carbonyl is attached to A, E is defined above and R.sub.2 represents hydrogen, hydroxy, alkyl, haloalkyl, alkoxyalkyl, alkoxy, aralkoxy, unsubstituted or substituted aryl, unsubstituted or substituted aralkyl or is as otherwise defined for R.sub.7 hereinafter;
• P is 0, 1 or 2;
• X.sub.1, X.sub.2 and X.sub.3 are independently hydrogen, hydroxy, alkoxy, alkylthio, hydroxyalkyl or hydroxybenzyl whereby at least one of X.sub.1, X.sub.2 and X.sub.3 is other than hydrogen;
• or X.sub.3 represents hydrogen and X.sub.1 and X.sub.2 together form a four or five membered bridge comprising elements selected from --O(CH.sub.2).sub.n' O--, ##STR395## and --S(CH.sub.2).sub.n' S--;
• R.sub.12 is hydrogen or alkyl,
• R.sub.13 and R.sub.14 are independently hydrogen, alkyl or halogen,
• m is one or two,
• n is zero, one or two, and
• n' is two or three.