Synthesis and Pesticidal Activities of New Quinoxalines

Abstract

Natural products are a source of many novel compounds with biological activity for the discovery of new pesticides and pharmaceuticals. Quinoxaline is a fused N-heterocycle in many natural products and synthetic compounds, and seven novel quinoxaline derivatives were designed and synthesized via three steps. Pesticidal activities of title quinoxaline derivatives were bioassayed. Most of these compounds had herbicidal, fungicidal, and insecticidal activities. The compounds 2-(6-methoxy-2-oxo-3phenylquinoxalin-1(2H)-yl)acetonitrile (3f) and 1-allyl-6-methoxy-3-phenylquinoxalin-2(1H)-one (3g) were the most active herbicides and fungicides. Mode-of-action studies indicated that 3f is a protoprophyrinogen oxidase-inhibiting herbicide. Compound 3f also possessed broad-spectrum fungicidal activity against the plant pathogen Colletotrichum species. Some of these compounds also had insecticidal activity. Molecular docking and DFT analysis can potentially be used to design more active compounds.

Targeted Amino Acid Substitutions in a Trichoderma Peptaibol Confer Activity against Fungal Plant Pathogens and Protect Host Tissues from Botrytis cinerea Infection

“…Natural products of plant or microbial origin have been pursued as starting points for the development of safer antimicrobial agents [ 6 ]. For plant protection, effective fungicides have been designed and developed starting from natural molecules, e.g., phenylquinoxalins, phenylpyrrole, and strobilurin-based fungicides [ 7 , 8 ]. Trichoderma spp.…”

Advances in Control Strategies against Spodoptera frugiperda. A Review

“…Another group of chemical insecticides is quinoxaline derivatives. The presence of the quinoxaline family has been described in natural products such as peptides, vitamins, and pharmaceuticals, and they have shown low to moderate toxicity in humans [ 20 , 21 , 22 ]. In the agricultural area, quinoxaline derivatives and di-N-oxides have been reported as active ingredients in pesticides and herbicides, with mechanisms of action on receptors such as phosphodiesterase in orders such as Blattodea and on cholinesterase in Coleoptera, Diptera, Hemiptera, and Lepidoptera insects.…”

Catalyst-free synthesis of novel 1,5-benzodiazepines and 3,4-dihydroquinoxalines using isocyanide-based one-pot, three- and four-component reactions

“…On the other hand quinoxalines show pharmacological properties such as antibiotic, 25 antimicrobial, 26 and antidiabetic 27 activity. They have also been shown to be pesticidal 28 and to inhibit aldose reductase 29,30 There are several procedures Scheme 1 Reported methods for the synthesis of (a) 1,5-benzodiazepine-2-carboxamides 4 and (b) 3,4-dihydroquinoxalin-2-amines 5.…”