Rational design of new agrochemical fungicides using substructural descriptors

Pest Management Science

Volumn 67, Issue 4, 2011, Pages 438-445

  Speck Planche, Alejandro ^a   Guilarte Montero, Lisvey ^b   Yera Bueno, Reider ^b   Rojas Vargas, Julio A ^b   García López, América ^b   Uriarte, Eugenio ^a   Molina Pérez, Enrique ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSIDAD DE ORIENTE   (Cuba)

^c UNIVERSIDAD DE CAMAGÜEY   (Cuba)

Author keywords

Agrochemical fungicides; Linear discriminant analysis; Molecular descriptors based on fragments; TOPS MODE

Indexed keywords

AGRICULTURAL CHEMICAL; FUNGICIDE;

AGROCHEMICAL; DATABASE; DISCRIMINANT ANALYSIS; FUNGICIDE; FUNGUS; PESTICIDE RESISTANCE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DESIGN; FACTUAL DATABASE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

AGROCHEMICALS; DATABASES, FACTUAL; DRUG DESIGN; FUNGICIDES, INDUSTRIAL; MOLECULAR STRUCTURE; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79952600178     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.2082     Document Type: Article

References (42)

1. Brent KJ and Hollomon DW, Fungicide Resistance in Crop Pathogens: How Can it be Managed? [Online]. Manuscript, Fungicide Resistance Action Committee, CROPLIFE INTERNATIONAL, Brussels, Belgium (2007). Available: .
2. Li M, Liu CL, Li L, Yang H, Li ZN, Zhang H, et al, Design, synthesis and biological activities of new strobilurin derivatives containing substituted pyrazoles. Pest Manag Sci 66: 107-112 (2009).
3. Liu A, Wang X, Chen C, Pei H, Mao C, Wang Y, et al, The discovery of HNPC-A3066: a novel strobilurin acaricide. Pest Manag Sci 65: 229-234 (2009).
4. Lopez-Ruiz FJ, Perez-Garcia A, Fernandez-Ortuno D, Romero D, Garcia E, de Vicente A, et al, Sensitivities to DMI fungicides in populations of Podosphaera fusca in south central Spain. Pest Manag Sci 66: 801-808 (2010).
5. Yang G, Jiang X and Yang H, Development of novel pesticides based on phytoalexins: Part 2. Quantitative structure-activity relationships of 2-heteroaryl-4-chromanone derivatives. Pest Manag Sci 58: 1063-1067 (2002).
6. Li XH, Yang XL, Ling Y, Fan ZJ, Liang XM, Wang DQ, et al, Synthesis and fungicidal activity of novel 2-oxocycloalkylsulfonylureas. J Agric Food Chem 53: 2202-2206 (2005).
7. Saiz-Urra L, Racero JC, Macias-Sachez AJ, Hernandez-Galan R, Hanson JR, Perez-Gonzalez M, et al, Synthesis and quantitative structure-antifungal activity relationships of clovane derivatives against Botrytis cinerea. J Agric Food Chem 57: 2420-2428 (2009).
8. Bordas B, Komives T and Lopata A, Ligand-based computer-aided pesticide design. A review of applications of the CoMFA and CoMSIA methodologies. Pest Manag Sci 59: 393-400 (2003).
9. Khambay BP, Batty D, Jewess PJ, Bateman GL and Hollomon DW, Mode of action and pesticidal activity of the natural product dunnione and of some analogues. Pest Manag Sci 59: 174-182 (2003).
10. Du H, Wang J, Hu Z, Yao X and Zhang X, Prediction of fungicidal activities of rice blast disease based on least-squares support vector machines and project pursuit regression. J Agric Food Chem 56: 10785-10792 (2008).
11. Balba H, Review of strobilurin fungicide chemicals. J Environ Sci Health B 42: 441-451 (2007).
12. Rugutt JK, Ngigi AN, Rugutt KJ and Ndalut PK, Native Kenyan plants as possible alternatives to methyl bromide in soil fumigation. Phytomedicine 13: 576-583 (2006).
13. Estrada E, Pena A and Garcia-Domenech R, Designing sedative/hypnotic compounds from a novel substructural graph-theoretical approach. J Comput Aided Mol Des 12: 583-595 (1998).
14. Estrada E, Uriarte E, Montero A, Teijeira M, Santana L and De Clercq E, A novel approach for the virtual screening and rational design of anticancer compounds. J Med Chem 43: 1975-1985 (2000).
15. Galvez J, Garcia-Domenech R, De Julian-Ortiz V and Soler R, Topological approach to analgesia. J Chem Inf Comput Sci 34: 1198-1203 (1994).
16. Garcia-Domenech R, Lopez-Pena W, Sanchez-Perdomo Y, Sanders JR, Sierra-Araujo MM, Zapata C, et al, Application of molecular topology to the prediction of the antimalarial activity of a group of uracil-based acyclic and deoxyuridine compounds. Int J Pharm 363: 78-84 (2008).
17. Gonzalez Diaz H, Olazabal E, Castanedo N, Sanchez IH, Morales A, Serrano HS, et al, Markovian chemicals 'in silico' design (MARCH-INSIDE), a promising approach for computer aided molecular design II: experimental and theoretical assessment of a novel method for virtual screening of fasciolicides. J Mol Model 8: 237-245 (2002).
18. Gonzalez-Diaz H, Olazabal E, Santana L, Uriarte E, Gonzalez-Diaz Y and Castanedo N, QSAR study of anticoccidial activity for diverse chemical compounds: prediction and experimental assay of trans-2-(2-nitrovinyl)furan. Bioorg Med Chem 15: 962-968 (2007).
19. Marrero-Ponce Y, Khan MT, Casanola-Martin GM, Ather A, Sultankhodzhaev MN, Garcia-Domenech R, et al, Bond-based 2D TOMOCOMD-CARDD approach for drug discovery: aiding decision-making in 'in silico' selection of new lead tyrosinase inhibitors. J Comput Aided Mol Des 21: 167-188 (2007).
20. Marrero-Ponce Y, Meneses-Marcel A, Rivera-Borroto OM, Garcia-Domenech R, De Julian-Ortiz JV, Montero A, et al, Bond-based linear indices in QSAR: computational discovery of novel anti-trichomonal compounds. J Comput Aided Mol Des 22: 523-540 (2008).
21. Speck-Planche A, Scotti MT, García-López A, Emerenciano VP, Molina-Pérez E and Uriarte E, Design of novel antituberculosis compounds using graph-theoretical and substructural approaches. Mol Divers 13: 445-458 (2009).
22. Speck-Planche A, Scotti MT, Emerenciano VP, García-López A, Molina-Pérez E and Uriarte E, Designing novel antitrypanosomal agents from a mixed graph-theoretical substructural approach. J Comput Chem 31: 882-894 (2010).
23. Viswanadhan VN, Ghose AK, Revankar GR and Robins RK, Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J Chem Inf Comput Sci 29: 163-172 (1989).
24. Viswanadhan VN, Reddy MR, Bacquet RJ and Erion MD, Assessment of methods used for predicting lipophilicity: application to nucleosides and nucleoside bases. J Comput Chem 14: 1019-1026 (1993).
25. Estrada E and Gutierrez Y, Modeling chromatographic parameters by a novel graph theoretical sub-structural approach. J Chromatogr A 858: 187-199 (1999).
26. Estrada E, Gutierrez Y and Gonzalez H, Modeling diamagnetic and magnetooptic properties of organic compounds with the TOPS-MODE approach. J Chem Inf Comput Sci 40: 1386-1399 (2000).
27. Estrada E and Uriarte E, Quantitative structure-toxicity relationships using TOPS-MODE. 1. Nitrobenzene toxicity to Tetrahymena pyriformis. SAR QSAR Environ Res 12: 309-324 (2001).
28. Estrada E, Molina E and Uriarte E, Quantitative structure-toxicity relationships using TOPS-MODE. 2. Neurotoxicity of a non-congeneric series of solvents. SAR QSAR Environ Res 12: 445-459 (2001).
29. Estrada E, Uriarte E, Gutierrez Y and Gonzalez H, Quantitative structure-toxicity relationships using TOPS-MODE. 3. Structural factors influencing the permeability of commercial solvents through living human skin. SAR QSAR Environ Res 14: 145-163 (2003).
30. Estrada E and Peña A, In silico studies for the rational discovery of anticonvulsant compounds. Bioorg Med Chem 8: 2755-2770 (2000).
31. Estrada E, Quincoces JA and Patlewicz G, Creating molecular diversity from antioxidants in Brazilian propolis. Combination of TOPS-MODE QSAR and virtual structure generation. Mol Divers 8: 21-33 (2004).
32. Estrada E, Spectral moments of the edge adjacency matrix in molecular graphs. 1. Definition and applications for the prediction of physical properties of alkanes. J Chem Inf Comput Sci 36: 844-849 (1996).
33. Estrada E, Spectral moments of the edge adjacency matrix in molecular graphs. 2. Molecules containing heteroatoms and QSAR applications. J Chem Inf Comput Sci 37: 320-328 (1997).
34. Estrada E, Spectral moments of the edge adjacency matrix in molecular graphs. 3. Molecules containing cycles. J Chem Inf Comput Sci 38: 23-27 (1998).
35. Estrada E and Molina E, Novel local (fragment-based) topological molecular descriptors for QSPR/QSAR and molecular design. J Mol Graph Model 20: 54-64 (2001).
36. Perez Gonzalez M, Gonzalez Diaz H, Molina Ruiz R, Cabrera MA and Ramos de Armas R, TOPS-MODE based QSARs derived from heterogeneous series of compounds. Applications to the design of new herbicides. J Chem Inf Comput Sci 43: 1192-1199 (2003).
37. Estrada E, Molina E and Perdomo-Lopez I, Can 3D structural parameters be predicted from 2D (topological) molecular descriptors? J Chem Inf Comput Sci 41: 1015-1021 (2001).
38. Wood A, Compendium of Pesticide Common Names. Classified List of Pesticides. [Online]. Available: .
39. O'Neill MJ, Heckelman PE, Koch CB and Roman KJ (eds), The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals. Merck & Co., Inc., Whitehouse Station, NJ (2006).
40. Talete srl. DRAGON for Windows (Software for Molecular Descriptor Calculations). Version 5.3, 2005. [Online]. Available: .
41. Estrada E and Gutiérrez Y, MODESLAB 15 © 2002-2004. [Online]. Available: .
42. STATISTICA (Data Analysis Software System), Version 6. [Online]. StatSoft, Inc. (2001). Available: .