Synthesis and herbicidal activity of novel heterocyclic protoporphyrinogen oxidase inhibitors

• Published in: Pest management science 2004-12, Vol.60 (12), p.1178-1188
• Main Authors: Meazza, Giovanni, Bettarini, Franco, Porta, Piero La, Piccardi, Paolo, Signorini, Ernesto, Portoso, Domenico, Fornara, Luca
• Format: Article
• Language: English
• Subjects: arylpyrroles; Biological and medical sciences; Chemical control; Crops; Enzymes; Fundamental and applied biological sciences. Psychology; Galium aparine; herbicide; Herbicides; Herbicides - chemical synthesis; Herbicides - pharmacology; Molecular Structure; Oxidoreductases Acting on CH-CH Group Donors - antagonists & inhibitors; Parasitic plants. Weeds; Phytopathology. Animal pests. Plant and forest protection; Plants, Edible; Protoporphyrinogen Oxidase; protox inhibitor; Pyrroles - chemical synthesis; Pyrroles - pharmacology; Weeds
• ISSN: 1526-498X; 1526-4998
• DOI: 10.1002/ps.923

Protox inhibitors are applied as foliar sprays, thus causing very rapid cellular collapse and desiccation of many troublesome weeds in the presence of light. In many respects, they appear to be ideal herbicides, because they act rapidly and do not harm mammals under normal conditions. The main limitation to their widespread adoption is that few crops are naturally resistant to them. Crop tolerance has mainly been pursued with the synthesis of the cyclic imide classes containing 5‐ and 6‐membered heterocycles, including pyrazole, pyridazine, 1,2,4‐triazine, triazolinone and trifluoromethyluracil derivatives. Because of their structural novelties and biological performance, active investigations on heterocyclic protox inhibitors have been carried out in our laboratories and we have found 3‐arylpyrroles to be a new class of light‐activated, membrane‐disrupting herbicides. They are active on both grass and broadleaf weeds at low rates. The synthesis and structure–activity relationships are presented. Copyright © 2004 Society of Chemical Industry