Design, synthesis and fungicidal activity of novel (E)-methyl 2-{2-[(coumarin-7-yloxy)methyl]phenyl}-3-methoxyacrylates

Natural Product Communications

Volumn 2, Issue 8, 2007, Pages 845-848

  Liu, Chang Ling ^a,b   Li, Miao ^a,b   Guan, Ai Ying ^a   Zhang, Hong ^a   Li, Zheng Ming ^b  

^a SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY   (China)

^b NANKAI UNIVERSITY   (China)

Author keywords

Coumarins; Fungicidal activity; Strobilurin; Synthesis

Indexed keywords

EID: 84897457360     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0700200811     Document Type: Article

References (19)

1. Murray RDH, Mendez J, Brown SA (1982) The Natural Coumarins: Occurrence, Chemistry and Biochemistry. John Wiley & Sons Ltd: New York.
2. Singh R, Gupta BB, Malik OP (1987) Studies on pesticides based on coumarin. I. Antifungal activity of 6-alkyl-3-n-butyl-7-hydroxy-4- methylcoumarins. Pesticide Science, 20, 125-130.
3. Daoubi M, Duran-Patron R, Hmamouchi M., Hernandez-Galan R, Benharref A, Collado IG (2004) Screening study for potential lead compounds for natural product-based fungicides: I. Synthesis and in vitro evaluation of coumarins against Botrytis cinerea. Pest Management Science, 60, 927-932.
4. Sukh D, Opender K. (1997) Insecticides of Natural Origin. Netherlands: Harwood academic publishers.
5. Gleye C, Lewin G, Laurens A., Jullian JC, Loiseau P, Bories C, Hocquemiller R. (2003) Acaricidal activity of tonka bean extracts. Synthesis and structure-activity relationships of bioactive derivatives. Journal of Natural Products, 66, 690-692.
6. Liu C-L, Zhong B., Li Z-M. (2003) Agrochemicals discovered and developed from natural leads (II)-insecticides and acaricide. Chinese Journal of Pesticides (Nong Yao), 12, 1-8.
7. Beriger E. (1978) Insecticidally active 3-N-(4-trifluoromethylphenyl)- carbamoyl-4-hydroxy-coumarin. US Patent 4078075.
8. Liu C-L, Han L., Li Z-M. (2004) Agrochemicals discovered and developed from natural lead compounds (III) herbicides. Chinese Journal of Pesticides (Nong Yao), 1, 1-4.
9. Alvarado SI, Marc PA, Dahlke B.J., Reilly-Horch E. (1997) 4-Phenoxycoumarins as herbicidal agents. US Patent 5681968.
10. Enomoto M, Nagano H, Haga T., Morita K, Sato M. (1988) Coumarin derivative, its production and herbicide containing said derivative as active component. JP 63267779.
11. Tomlin CDS. (2003) The Pesticide Manual. 13th ed. 52-53.
12. Tomlin CDS. (2003) The Pesticide Manual. 13th ed. 595-596.
13. Tomlin CDS. (2003) The Pesticide Manual. 13th ed. 786-787.
14. Clough JM, de Fraine PJ, Fraser TEM, Godfrey CRA. (1992) In Synthesis and Chemistry of Agrochemicals III, ACS Symposium Series 504, Washington D C: American Chemical Society, 372-384.
15. Liu C-L. (1998) Recent advance on methoxyacrylate fungicides. Chinese Journal of Pesticides (Nong Yao). 3, 1-6.
16. Liu C-L, Li Z-M. (2003) Discovery of strobin fungicides. Chinese Journal of Pesticides (Nong Yao), 3, 43-48.
17. 3, 4, 5a, 5b and 5d are available from chemical reagent company; others were prepared based on the known method: Xie L, Takeuchi Y, Cosentino M, McPhail AT, Lee K.-H. (2001) Synthesis and anti-HIV activity of disubstituted (3'R, 4'R)-3',4'-di O-(S)-camphanoyl-(+)-cis-khellactone analogues. Journal of Medicinal Chemistry, 44, 664-671.
18. (a) Liu C-L, Li Z-M. (2004) Design, synthesis, and biological activity of a novel lead compound 4-[4-(3,4-dimethoxyphenyl)-2-methylthiazole-5-carbonyl] morpholine. Chinese Journal of Pesticides (Nong Yao), 4, 157-159
19. (b) Liu C-L, Li L, Li Z-M. (2004) Design, synthesis, and biological activity of novel 4-(3,4-dimethoxyphenyl)-2-methylthiazole-5-carboxylic acid derivatives. Bioorganic & Medicinal Chemistry, 12, 2825-2830.