Abstract
This is the first report showing that 3-(dichlorophenyl)isocoumarins and (±)-3,4-dihydroisocoumarins are plant and plant fungus growth inhibitors. 3-Dichlorophenylisocoumarins were synthesized by condensation of homophthalic acid with dichlorobenzoyl chlorides. The alkaline hydrolysis of these isocoumarins afforded keto acids. Racemic 3-(Dichlorophenyl)-3,4-dihydroisocoumarins were obtained by reduction of keto acids to racemic hydroxy acids, followed by cyclodehydration using acetic anhydride. The herbicidal, fungicidal and insecticidal activities of the synthesized compounds have been evaluated. Some of the synthesized compounds show excellent herbicidal and fungicidal activities but none of the synthesized compounds presented any insecticidal effects on the test insects. The findings of this study suggest that isocoumarins and related compounds may serve as lead compounds towards the design of bioactive herbicides and fungicides.
Highlights
Weeds compete with crops for sunshine, water, nutrients, and physical space and are capable of greatly influencing the growth of crops and undermining both crop quality and yield
Direct condensation of the acid chlorides 2(ac) with homophthalic acid at 200 °C afforded the 3(dichlorophenyl)isocoumarins 3(a-c), which were purified by column chromatography and showed a single spot on TLC
The melting points of the compounds were determined in open capillaries using a Gallenkemp melting point apparatus and are uncorrected
Summary
Weeds compete with crops for sunshine, water, nutrients, and physical space and are capable of greatly influencing the growth of crops and undermining both crop quality and yield. Many weeds are the harbor or nest of pathogens, viruses, and pests, which may result in the occurrence and spread of plant diseases and insect pests in crops. Herbicides, as the main weed control tool, play a very important role in modern agriculture. Over the last two decades, there has been a dramatic increase in the rate of superficial and invasive fungal infections.[3,4,5,6,7] Modern agriculture relies on effective control of fungal diseases to increase crop yield and quality and increase crop value.[8] No single fungicide can be used for all disease situations and the widespread
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