The Synthesis and Herbicidal Activity of 1-Alkyl-3-(α-hydroxysubstituted benzylidene)pyrrolidine-2,4-diones

In the search for better herbicides a series of 1-alkyl-3-(α-hydroxy-(un)substituted benzylidene)pyrrolidine-2,4-diones were prepared and their structure-activity relationships studied. All their structures have been confirmed by 1 H-NMR and elemental analysis. The preliminary bioassay results indicated that some of them have high herbicidal activity against annual dicotyledonous and monocotyledonous plants. Keywords: Pyrrolidine, herbicides, inhibition. Introduction The inhibitors of 4-hydroxyphenylpyruvate dioxygenase (HPPD, EC 1.13.11.27) constitute a new kind of herbicides [1]. Generally, potent herbicides of this kind must possess the following structural features: 1) a tricarbonyl methane structure and one of the three carbonyl groups must be a subustituted benzoyl group; 2) the compound must be able to enolise so that the enolate is capable of inhibiting HPPD enzyme by competitive combination with Fe 2+ – the reaction center of HPPD enzyme [2]. Recently, we observed that the 3-acyltetramic acids form an expanding group of antibiotics and pigments derived from microorganisms [3]. They display a range of biological activities [4] and all compounds of this kind possess a tricarbonyl methane structure and can essentially enolise completely (the chemical shifts of their enolic hydroxyls were larger than 10). Tests of their antimicrobial activities indicated that the structure of the acyl substituent at the 3-position and possession of a 3