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Herbicidal properties of new N-amino-1,4-endocyclohex-5-ene-2,3-dicarboximide derivatives

M. Furdík, E. Sidóová, and S. Priehradný

Komenský University, Bratislava

 

Abstract: The prepn. of unknown derivs. of N-amino-l,4-endocyclohex-5-ene-2,3-dicarboximide was described. These were synthesized in order to study the relationship between the structural changes caused by the substitution on the N-amino group and the herbicidal activity. These were prepd.: monoacyl derivs., by acyl chlorides in the presence of benzene and N,N-diethylaniline, N-(acetamido), decompd. 183-5°, N-(chloroacetamido), decompd. 152-5°, N-(phenacetylamino), decompd. 152-4°, N-(benzoylamino), decompd. above 151°, and N-(furoylamino), decompd. above 177°, and by acetylation, N-(diacetylamino), decompd. 146.5-6.5°; N-(anilino), decompd. 189-91°, N-(p-nitroanilino), decompd. 189-92°, and N-(2,4 dinitroanilino), decompd. 233.5-5.5°, with phenylhydrazine and its nitro derivs. in water or glacial CH3COOH medium; N-benzalamino derivs. with the condensation with benzaldehyde and its derivs., N-(o-chlorobenzalamino), decompd. 153.5°, N-(p-chlorobenzalamino), m.p. 159-60°, N-(o-nitrobenzalamino), m.p. 149-51°, N-(m-nitrobenzalamino), decompd. 152-4°, N-(p-nitrobenzalamino), decompd. 163-5°, N-(o-hydroxybenzalamino), decompd. 163-4°, and N-(p-dimethylaminobenzalamino), decompd. above 191°, and by the anhydride of 1,4-endocyclohex-5-ene-2,3-dicarboxylic acid on hydrazine hydrate, bis(1,4-endocyclohex-5-ene-2,3-dicarboximide), decompd. above 176°. All the tested compds. showed lower herbicidal properties than the standard products and were more effective at the higher concns. of the active compd. The most active was N-(2,4-dinitrophenylamino) deriv.

Full paper in Portable Document Format: 198a611.pdf (in Slovak)

 

Chemical Papers 19 (8) 611–619 (1965)

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