2000, Cantin Sanz, Angel, Moya Sanz, Mª del Pilar, Miranda Alonso, Miguel Ángel, Primo Millo, Jaime, Primo Yufera, Eduardo, Instituto Universitario Mixto de Tecnología Química, Instituto Agroforestal Mediterráneo, Departamento de Química, Centro de Ecología Química Agrícola, Escuela Técnica Superior de Ingeniería Industrial

[EN] New analogues of the bioactive enamides isolated from P. brevicompactum (2 and 3) have been synthesized to improve the biological activities. Two different structural modifications have been introduced: substitution of the aliphatic side chain present in the natural products (1-4) by other groups frequently found in other active compounds and use of other nitrogen-containing five-membered rings with different degrees of oxidation. In this way, the insecticidal and fungicidal activities have been improved. Thus, compound 9, which posseses a 3-pyrroline ring, exhibited important insecticidal activity against third-instar nymphs of Oncopeltus fasciatus Dallas (100% mortality at 7.5 mu g/cm(2)). Remarkable fungicidal activity was also found, and preliminary structure-activity relationships could be established.

2000, Castillo López, María Ángeles, Moya Sanz, Mª del Pilar, Hernández Giménez, Enrique, Primo Yufera, Eduardo, Departamento de Biotecnología, Instituto Agroforestal Mediterráneo, Centro de Ecología Química Agrícola, Centro Avanzado de Microbiología Aplicada, Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural, Comisión Interministerial de Ciencia y Tecnología, Generalitat Valenciana

[EN] The effectiveness of seven strains of entomopathogenic fungi against Ceratitis capitata adults was evaluated in the laboratory. Adults were susceptible to five of seven aqueous suspensions of conidia. Metarhizium anisopliae and strain CG-260 of Paecilomyces fumosoroseus were the most pathogenic fungi, with 10- day LD50 values of 5.1 and 6.1 3 103 conidia/fly, respectively, when applied topically. Sublethal effects on fecundity and fertility of the fungal-exposed females were also studied. The most effective fungus in reducing fecundity was P. fumosoroseus CECT 2705, with reductions on the order of 65% at 1 3 106 conidia/fly. M. anisopliae and Aspergillus ochraceus also showed significant reductions of fecundity (40–50% for most of the assayed concentrations). Fertility was moderately affected by the fungi. M. anisopliae at 1 3 106 conidia/fly was the most effective fungus, showing egg eclosion reduction of over 50% compared with the control. In addition, culture broth dichloromethane extracts from the entomopathogenic fungi were tested for insecticide activity against C. capitata, including effects on fecundity and fertility. The extract from M. anisopliae was the most toxic, resulting in about 90% mortality at a concentration of 25 mg/g of diet; under these conditions, fecundity and fertility of treated females were reduced by 94 and 53%, respectively, compared with untreated controls. © 2000 Academic Press

1999, Moya Sanz, Mª del Pilar, Cantin Sanz, Angel, Miranda Alonso, Miguel Ángel, Primo Millo, Jaime, Primo Yufera, Eduardo, Instituto Universitario Mixto de Tecnología Química, Instituto Agroforestal Mediterráneo, Departamento de Química, Centro de Ecología Química Agrícola, Escuela Técnica Superior de Ingeniería Industrial

[EN] To evaluate the effect of simplifying the ß-ketoamide system present in active isolated metabolites from Penicillium brevicompactum (2 and 3) on the activity, new analogues with a monocarbonylic amide functionality have been obtained. In this way, the insecticidal and fungicidal activities have been improved in relation to the natural products taken as lead molecules. Thus, two of the synthetic analogues (5a and 5b) showed very important insecticidal activities against third-instar nymphs of Oncopeltus fasciatus Dallas, with acute LD50 values of 3.0 and 1.5 ¿g/cm2, respectively. Moreover, some analogues showed good levels of fungicidal activity against a wide range of commercially important and taxonomically diverse fungi; remarkably, compound 7c has proved to be highly active against Colletotrichum gloesporoides and Colletotrichum coccodes, with ED50 values of 2.04 and 11.7 ¿g/mL, respectively.

1999, Cantin Sanz, Angel, Moya Sanz, Mª del Pilar, Castillo López, María Ángeles, Primo Millo, Jaime, Miranda Alonso, Miguel Ángel, Primo Yufera, Eduardo, Instituto Universitario Mixto de Tecnología Química, Departamento de Biotecnología, Instituto Agroforestal Mediterráneo, Departamento de Química, Centro de Ecología Química Agrícola, Escuela Técnica Superior de Ingeniería Industrial, Centro Avanzado de Microbiología Aplicada, Escuela Técnica Superior de Ingeniería Agronómica y del Medio Natural

[EN] Two new natural products, N-(2-methyl-3-oxodec-8-enoyl)-2-pyrroline (2) and 2-(hept-5-enyl)-3-methyl-4-oxo-6,7,8,8a-tetrahydro-4H-pyrrolo[2,1-b]-1,3-oxazine (3), have been isolated from Penicillium brevicompactum Dierckx. Compound 2 has shown an important in vivo anti-juvenile-hormone (anti-JH) activity while compound 3 has exhibited insecticidal activity against Oncopeltus fasciatus Dallas. Both products have been synthesized starting from 1,4-hexadiene, by means of a sequence of reactions which includes the preparation of 6-octenoic acid and its transformation into the corresponding acid chloride, in order to acylate Meldrum's acid. Subsequent aminolysis with pyrrolidine, followed by methylation at the activated position of the ß-oxo amide with iodomethane, introduction of a methoxy group at the pyrrolidine ring by anodic oxidation and final elimination of methanol on SiO2 led to 2 and 3. The fact that both metabolites can be prepared by the same sequence indicates that they must be biogenetically related. Based on structural similarities, compounds 2 and 3 are also closely related to the recently discovered brevioxime