IE38049B1 - Novel phthalimido derivatives - Google Patents

Abstract

1395104 Substituted phthalimides AMERICAN CYANAMID CO 2 Aug 1973 [21 Aug 1972 5 April 1973] 36836/73 Heading C2C The invention comprises compounds of Formulae I and II wherein W is hydrogen or C 1 to C 4 alkyl; X and X<SP>1</SP> each represents hydrogen, halogen, C 1 to C 4 alkyl, CF 3 , C 1 to C 4 alkoxy, benzyloxy, di- (C 1 to C 4 )alkylamino, C 1 to C 4 alkylthio, hydroxy, C 1 to C 4 alkylsulphonyl, C 1 to C 4 alkanoylamino or nitro, with the proviso that at least one of X and X<SP>1</SP> is a substituent other than hydrogen; Y is -COOR 3 , -CONHR 3 , -CONR 3 R 4 , -CONHN(R 5 ) 2 , -CN or -COR 7 , R 1 and R 2 each represent C 1 to C 4 alkyl or when taken together with the carbon to which they are attached form C 4 to C 11 cycloalkyl optionally substituted with methyl; R 3 and R 4 each represent hydrogen or C 1 to C 4 alkyl; R 5 and R 6 each represent C 1 or C 2 alkyl; R 7 is halogen, R 8 is -CH 3 or where Z and Z<SP>1</SP> are hydrogen, C 1 or C 2 alkyl, halogen, -CF 3 or -OCH 3 and # is a single or double bond with the proviso that there be only 0 or 1 double bond in the ring. They may be prepared by nucleophilic substitution reactions between the appropriate amino compound of formula NH 2 CR 1 R 2 Y with an o-phthalic acid derivative of the Formulae III or V where X, X<SP>1</SP>, W, R 1 , R 2 and Y are as defined above except that Y is not -COR 7 and T 1 and T 2 are the nueleophilic substituents to be displaced, e.g. Cl or C 1 to C 4 alkoxy. When Y is -COR 7 , the desired acid halide is produced through the additional step of halogenating the appropriate carboxylic acid (Y being -COOH) with a conventional halogenating agent. Alternatively, the amino compound of formula NH 2 CR 1 R 2 Y may be reacted with the appropriate phthalic anhydride of Formulae VI or VIII where X, X<SP>1</SP>, Y, W, R 1 and R 2 are as defined above except that Y is not -COR 7 , the latter compounds being formed from the carboxylic analogues as described above. The phthalic anhydride derivatives of Formulae VI and VII may be prepared by dehydration of the corresponding acid. The acid halides prepared as above may be converted to the corresponding amide by reaction with ammonia, dialkyamine or dialkyl hydrazine. Phthalimido acetamides in which R 4 is hydrogen may be prepared by reacting the appropriate phthalic, tetrahydro- or hexahydrophthalic anhydride with the appropriate α,α - disubstituted - α - amino nitrile to give the corresponding phthalamic acid, which is then cyclized to give the phthalimido, tetra- or hexahydrophalimido nitrile, followed by hydration. To form the hydrozinium halide, an amide of formulae is reacted with an alkyl halide. The tetra- and hexahydrophthalimido hydrazinium salts may also be prepared in like manner. Phthalimido esters of formulae may be prepared by reacting a C 1 -C 4 diazoalkane with the corresponding acid, i.e. where R 3 is hydrogen. Alternatively, the phthalic, tetra- or hexahydrophthalic anhydride may be reacted with the appropriate α-amino ester, or the acid halide may be reacted with a C 1 -C 4 alkanol in the presence of an acid acceptor. The phthalimido nitrile may be obtained by dehydration of the corresponding amide. The compounds of Formulµ I and II may also be prepared by reacting a compound of formula where R 1 , R 2 and Y are as above, except that Y cannot be -COR 7 or with a substituted phthaloyl chloride of formula They may also be prepared by reacting the compound where W, X and X<SP>1</SP> are as above and R 9 is C 1 -C 4 alkyl, with a compound of formula where R 1 , R 2 and Y are as above, except that Y cannot be -COR 7 or to give a product which can then be cyclized. The compounds of Formulae I and II above except those in which Y is -COR 7 together with those in which both X and X<SP>1</SP> are hydrogen may be used as plant growth regulating agents. [GB1395104A]