Synthesis and Bioactivity of Novel Coumarin Derivatives

A series of coumarin derivatives (6-8) containing (E)-methyl 2-(methoxyimino)-2-phenylacetate, (E)-2-(methoxyimino)-N-methyl-2-phenylacetamide and methyl methoxy(phenyl)carbamate were synthesized from substituted resorcinols (1) and substituted β-keto esters (2) as starting material via cyclization...

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Bibliographic Details
Published in:Natural product communications 2011-12, Vol.6 (12), p.1917-1920
Main Authors: Guan, Ai-Ying, Liu, Chang-Ling, Li, Miao Li, Zhi-Nian, Zhang, Ming-Xing, Zhang, Hong
Format: Article
Language:English
Subjects:
Animals
Coumarins - chemical synthesis
Coumarins - pharmacology
Fungicides, Industrial - pharmacology
Insecticides - pharmacology
Structure-Activity Relationship
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Summary:A series of coumarin derivatives (6-8) containing (E)-methyl 2-(methoxyimino)-2-phenylacetate, (E)-2-(methoxyimino)-N-methyl-2-phenylacetamide and methyl methoxy(phenyl)carbamate were synthesized from substituted resorcinols (1) and substituted β-keto esters (2) as starting material via cyclization and condensation reactions. The test results indicated that (E)-methyl 2-{2-[(3-hexyl-4-methyl-coumarin-7-yloxy)methyl]phenyl}-2-(methoxyimino)acetate (6f) was the optimal structure with good fungicidal activity against cucumber grey mold (CGM) giving 100% control at 100 mg L−1 concentration, much higher than that of coumoxystrobin. Methyl 2-[(3,4-dimethyl-coumarin -7-yloxy)methyl]phenyl(methoxy)carbamate (8a) was another optimal structure with good fungicidal activity against wheat powdery mildew (WPM) showing 100% control at 50 mg L−1 concentration, at the same level as that of the commercial kresoxim-methyl, and very significantly higher than that of coumoxystrobin (no control against WPM at 400 mg L−1).
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1100601232