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 beta-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)).
State Key Laboratory of the Discovery and Development of Novel Pesticide, Shenyang Research Institute of Chemical Industry Co. Ltd., Shenyang 110021, China.
Ai-Ying
AY
Guan
Chang-Ling
CL
Liu
Miao
M
Li
Zhi-Nian
ZN
Li
Ming-Xing
MX
Zhang
Hong
H
Zhang
D000818:Animals; D003374:Coumarins / Q000138:chemical synthesis* / Q000494:pharmacology*; D005659:Fungicides, Industrial / Q000494:pharmacology; D007306:Insecticides / Q000494:pharmacology; D013329:Structure-Activity Relationship
D003374:Coumarins; D005659:Fungicides, Industrial; D007306:Insecticides