Abstract
Twenty novel cinnamamide derivatives were designed and synthesized using as lead compound pyrimorph, whose morpholine moiety was replaced by β-phenylethylamine. All the compounds were characterized by their spectroscopic data. The fungicidal and insecticidal activities were also evaluated. The preliminary results showed that all the title compounds had certain fungicidal activities against seven plant pathogens at a concentration of 50 μg/mL, and compounds 11a and 11l showed inhibition ratios of up to 90% against R. solani. Most of the title compounds exhibited moderate nematicidal activities. In general, the morpholine ring may be replaced by other amines and a chlorine atom in the pyridine ring is helpful to fungicidal activity.
Highlights
Cinnamides constitute an important class of compounds with a variety of biological properties, such as nervous central system depressant, anticonvulsant, muscle relaxant, antiallergic, antineoplastic and anti-infective activities, etc. [1,2,3,4,5,6,7]
Mandipropamide (4), which controls foliar diseases caused by oomycetes, is a typical representative of β-phenylethylamines derivitives used in agrochemistry [16,17]
Tis is attributed to the fact that in the cis-form the electron-rich carbonyl oxygen has a tendency to donate electrons to the electron-deficient pyridine ring, which leads to the formation of the more stable intermediate and the cis-product 9
Summary
Cinnamides constitute an important class of compounds with a variety of biological properties, such as nervous central system depressant, anticonvulsant, muscle relaxant, antiallergic, antineoplastic and anti-infective activities, etc. [1,2,3,4,5,6,7]. Cinnamides constitute an important class of compounds with a variety of biological properties, such as nervous central system depressant, anticonvulsant, muscle relaxant, antiallergic, antineoplastic and anti-infective activities, etc. Molecules 2011, 16 cinnamide fungicides, for example dimethomorph (1) [10], fluormorph (2) [11] and pyrimorph (3) [12,13], have been successfully developed. Pyrimorph, containing a morpholine ring and a pyridine ring, is a novel fungicide developed by our lab that exhibited excellent activity against oomycetes [14,15]. Β-phenylethylamines are very important bioactive molecules that can be found in many natural and synthetic drugs. Mandipropamide (4), which controls foliar diseases caused by oomycetes, is a typical representative of β-phenylethylamines derivitives used in agrochemistry [16,17].
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