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

Volumn 60, Issue 9, 2004, Pages 927-932

  Daoubi, Mourad ^a   Durán Patrón, Rosa ^b   Hmamouchi, Mohamed ^c   Hernández Galán, Rosario ^b   Benharref, Ahmed ^a   Collado, Isidro G ^b  

^a FACULTÉ DES SCIENCES SEMLALIA   (Morocco)

^b UNIVERSITY OF CÁDIZ   (Spain)

^c MOHAMMED V UNIVERSITY   (Morocco)

Author keywords

Antifungal activity; Botrytis cinerea; Coumarins; Crop protection agents

Indexed keywords

COUMARIN DERIVATIVE; DIHYDROPYRANOCOUMARIN DERIVATIVE; FUNGICIDE; LEAD; UNCLASSIFIED DRUG;

DISEASE CONTROL; FUNGAL DISEASE; FUNGICIDE; MONITORING; PATHOGEN;

ANTIFUNGAL ACTIVITY; ARTICLE; BOTRYTIS CINEREA; CHEMICAL STRUCTURE; CROP PROTECTION; FUNGAL METABOLISM; FUNGICIDAL ACTIVITY; MELTING POINT; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

BOTRYOTINIA FUCKELIANA; BOTRYTIS; FUNGI;

EID: 4344687551     PISSN: 1526498X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ps.891     Document Type: Article

References (24)

1. Epton HAS and Richmond DV, Formation, structure and germination of conidia, in The biology of Botrytis, ed by Coley-Smith JR, Verhoeff K and Jarvis WR, Academic Press, London, pp 41-83 (1980).
2. Apladasarlis P, Liapis KS and Miliadis GE, Study of procymidone and propargite residue levels resulting from application to greenhouse tomatoes. J Agric Food Chem 42:1575-1577 (1994).
3. Paris-Palacios S, Biagianti-Risbourg S and Vernet G, Hepatic disorders induced by a sublethal concentration of procymidone (fungicide dicarboximide) in Brachydanio rerio (Teleostei, Cyprinidae): histo-cytological approach. Bull Fr Peche Piscic 350-351:547-562 (1998).
4. Sala C, Fort F, Busto O, Zamora F, Arola L and Guasch J, Fate of some common pesticides during vinification process. J Agric Food Chem 44:3668-3671 (1996).
5. Lodovica Gullino M, Leroux P and Smith CM, Uses and challenges of novel compounds for plant disease control. Crop Prot 19:1-11 (2000).
6. Deighton NM, Muckenschnabel I, Colmenares AJ, Collado IG and Williamson B, Botrydial is produced in plant tissues infected by Botrytis cinerea. Phytochemistry 57:689-692 (2001).
7. Colmenares AJ, Aleu J, Durán-Patrón R, Collado IG and Hernández-Galán R, The putative role of botrydial and related metabolites in the infection mechanism of Botrytis cinerea. J Chem Ecol 28:997-1005 (2002).
8. Collado IG, Hanson JR and Macías-Sánchez AJ, Derivados clovánicos 2-O, 9 sustituidos y su preparación, para el tratamiento de infecciones producidas por hongos fitopatógenos, como agentes fungiestáticos de bajo impacto ecológico. Spanish Patent ES2154185 (2001); Chem Abs 135:195 688 (2001).
9. Collado IG, Hanson JR and Aleu J, Derivados con esqueleto probotriano y su preparación, para el tratamiento de infecciones producidas por hongos fitopatógenos, como agentes fungiestáticos de bajo impacto ecológico. Spanish Patent ES2154199 (2001); Chem Abs 135:195 688 (2001).
10. Collado IG, Hanson JR, Macías-Sánchez AJ and Mobbs D, The biotransformation of some clovanes by Botrytis cinerea. J Nat Prod 61:1348-1351 (1998).
11. Murray RDH, Mendez J and Brown SA, The natural coumarins: ocurrence, chemistry and biochemistry, John Wiley & Sons Ltd, New York (1982).
12. Walter MW, Structure-based design of agrochemicals. Nat Prod Rep 19:278-291 (2002).
13. Durán-Patrón R, Colmenares AJ, Hernández- Galán R and Collado IG, Some key metabolic intermediates in the biosynthesis of botrydial and related compounds. Tetrahedron 57:1929-1933 (2001).
14. Massanet GM, Pando E, Luis FR and Salva J, Synthesis of 3-(1′,1′-dimethylallyl)coumarins: gravelliferone, chalepin and rutamarin. Heterocycles 26:1541-1548 (1987).
15. Hernández Galán R, Massanet GM, Pando E, Luis FR and Salva J, Synthesis of (±)-3-(1′,1′-dimethylallyl)decursinol and 3-(1′,1′-dimethylallyl)-xanthyletin. Heterocycles 27:775-778 (1988).
16. Zubía E, Luis FR, Massanet GM and Collado IG, An efficient synthesis of furanocoumarins. Tetrahedron 48:4239-4246 (1992).
17. Borges del Castillo J, Rodríguez Luis F, Rodríguez Ubis JC and Lucas MS, Componentes de la Ruta Montana Mill. Rev Latinoamer Quim 16:15-18 (1985).
18. Murray RDH, Coumarins. Nat Prod Rep 6:591-624 (1989).
19. Hernández Galán R, Massanet GM, Pando E, Luis FR and Salvá J, Sigmatropic rearrangements in synthesis of C-8 prenylated 3-(1′,1′-dimethylallyl)coumarins: 3-(1′,1′- dimethylallyl)seselin. Heterocycles 29:297-300 (1989).
20. Collado IG, Massanet GM and Alonso MS, Nucleophilic 1,2 addition of bromine by perbromide reagents. Tetrahedron Lett 32:3217-3220 (1991).
21. Murray RDH, Ballantyne MM and Mathai KP, A method to introduce a 3,3-dimethylallyl unit ortho to a phenol. Tetrahedron Lett 3:243-244 (1970).
22. Borges del Castillo J, Rodríguez-Ubis JC and Rodríguez Luis F, Síntesis de varias dihidrofurocumarinas y dihidropiranocumarinas naturales. An Quim 81:106-109 (1985).
23. Chattannavar SN, Kulkarni S and Hegde RK, Bioassay of non/systemic fungicides against the wheat pathogen Drechslera sativus (Pam, King and Bakke). Pesticides 33-34 (1985).
24. Patil IS, Kulkarni S and Hegde RK, Bioassay of fungicides against Drechslera sorokiniana (Sacc). Pesticides 30-31 (1986).