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A Semi-Field Approach to Testing Botanical Insecticides. Effects of Natural and Analogues Annonaceous Acetogenins on Spodoptera frugiperdaSmith (Lepidoptera: Noctuidae)

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Journal of Agricultural Chemistry and Environment 2021年第4期10卷 458-468页

作者： José Ruiz Hidalgo María Gabriela Murúa adriana neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina Instituto de Tecnologia Agroindustrial del Noroeste Argentino (ITANOA) Estación Experimental Agroindustrial Obispo Colombres (EEAOC)-CONICET Las TalitasTucumán Argentina Facultad de Ciencias Naturales e Instituto Miguel Lillo UNT Miguel Lillo San Miguel de Tucumán

Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Spodoptera frugiperda is a pest that affects corn crops among others and has a great capacity to develop resistance to traditional insecticides, which represents sufficient reasons for the search for new alternatives for their control. The objective of this study was to determine the appropriate concentration and screening new natural insecticides against second instar larvae of S. frugiperda, under glasshouse conditions on Zea mays L. Natural products such as annonaceous acetogenins and some acetylated and methoxy methylated ACG derivatives and the commercial product Lambda-cyhalotrin (LC) were evaluated. The percent mortalities of S. frugiperda larvae in glasshouse conditions were recorded after 24, 48 and 72 h of treatment application. The results showed that the acetogenins tested were significantly (P 5) (100 μg/mL) + squamocin (6) (100 μg/mL) + LC (50 μg/mL) that proved the most effective and gave (100%), while rolliniastatin-2 (5) at 100 μg/mL alone, gave lowest percent mortality (65%), followed by squamocin (6) at 100 μg/mL (55%) and LC at 50 μg/mL (30%). The acetylated and methoxy methylated ACGs derivatives caused very low mortality (25% - 35%). It is recommended the mixture as a management option of S. frugiperda as a component of integrated pest management. The results allow us to infer that the addition of natural ACGs synergizes the insecticidal activity of the commercial product. Finding a new ecological alternative for insect control.

关键词： Annonaceous Acetogenins Biocides Spodoptera frugiperda

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Insecticidal Activity of Annonaceous Acetogenins and Their Derivatives on Spodoptera frugiperdaSmith (Lepidoptera: Noctuidae)

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Journal of Agricultural Chemistry and Environment 2018年第3期7卷 105-116页

作者： José Ruiz Hidalgo Eduardo A. Parellada Alicia Bardón Nancy Vera adriana neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina Inquinoa-Conicet Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina Instituto de Farmacia Facultad de Bioquímica Química y Farmacia UNT Tucumán Argentina

Background: Annonaceous acetogenins enclose a large number of biological activities, among which the insecticidal stands out. Methods: We report herein the biocide effects of natural acetogenins from Annona squamosa, A.?muricata and A. montana seeds: annonacin, cis-annonacin, cis-annonacin-10- one, asimicin, rolliniastatin-2, cherimolin-1, cherimolin-2, almuñequin, and two β-OH acetogenins: laherradurin and itrabin on Spodoptera frugiperda Smith (Lepidoptera: Noctuidae). Also, some acetylated and methoxy methylated ACG derivatives were synthesized and evaluated: annonacin (3 OAc), annonacin (4 OAc), asimicin (3 OAc), rolliniastatin-2 (3 OAc), rolliniastatin-2 (MOM), laherradurin (3 OAc) and itrabin (3 OAc). Results: The natural acetogenin rolliniastatin-2 (100 μg·g-1 of diet) produced the most important toxic action causing 100% mortality of early instar larvae. Derivatization of ACG yielded compounds that produced nutritional alterations. The incorporation of rolliniastatin-2 (3 OAc) and rolliniastatin-2 (3 MOM) (100 μg·g-1) into the artificial diet of Spodoptera frugiperdadisplayed the strongest antifeedant effects causing marked decreasings in larval growth and adult lethal malformations. Conclusion: Natural acetogenins are promising metabolites for insect control. Derivatization of these compounds reduces their toxicity to early instar larvae.

关键词： Annonaceous Acetogenins Biocides Spodoptera frugiperda

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Insecticidal Effects of the Annonaceous Acetogenin Squamocin and the Acetogenin Fraction of Seeds of Rollinia occidentalison Soybean and Corn Pests

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Journal of Agricultural Chemistry and Environment 2014年第4期3卷 156-160页

作者： Diego Tolosa José Ruiz Hidalgo Pedro Eugenio Sal Susana Popich Alicia Bardón adriana neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina Universidad Nacional de Chilecito Chilecito Argentina INQUINOA-CONICET Tucumán Argentina

A treatment based on the acetogenin fraction of the methanol extract of Rollinia occidentalis seeds was applied to soybean crops for three consecutive years. In relation to the control population, the treatment reduced the population of Anticarsia gemmatalis, Rachiplusia nu, Pseudoplusia includens, Loxostege bifidalis and Spodoptera frugiperda to 52% and 65% after 48 h of application at concentrations of 500 and 750 μg/mL respectively, while low toxic effects were detected on natural enemies. The extract treatment at 500 μg/mL and a solution of the annonaceous acetogenin, squamocin, at 50 and 100 μg/mL, were also applied to a corn field to produce 75%, 93% and 100% mortality rates on the population of S. frugiperda, respectively, after 72 h of application. In addition, damages caused by lepidopterans in treated crops were lower than those observed in non treated fields, evaluated by residual biomass. This statement is based on data from trials with the commercially available insecticides lufenuron and cypermethrin.

关键词： Annonaceous Acetogenins Polyphagous Lepidopteran Soybean Crops Corn Crops Spodoptera frugiperda

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Natural and Derivatized Acetogenins Promising for the Control of Spodoptera frugiperda Smith

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Journal of Agricultural Chemistry and Environment 2016年第4期5卷 200-210页

作者： José Ruiz Hidalgo Eduardo Alberto Parellada Lilian Di Toto Blessing Alicia Bardón Keshav Lalit Ameta Nancy Vera adriana neske UNT-FBQF-Argentina Institutode Química Orgánica Tucumán Argentina INQUINOA-CONICET Tucumán Argentina Department of Science Mody University of Science and Technology FASC Lakshmangarh India UNT-FBQF-Argentina Instituto de Farmacia Tucumán Argentina

Annonaceous acetogenins (ACG), belonging to the family Annonaceae, represent a class of bioactive compounds whose toxic effects have been reported for several spe-cies of insects. Given their insecticidal properties, we first carried out the isolation of the ACG from a Brazilian collection of the seeds of Annona squamosa (Annonaceae) and prepared their methoxy methylated (MOM) and acetylated (OAc) derivatives by chemical methods. ACG analogues were semi-synthesized and characterized by spec-troscopic techniques (1H and 13C-NMR). We isolated ten natural acetogenins: squamo-cin, molvizarin, motrilin, rolliniastatin-2, almunequin, cherimolin-1, cherimolin-2, an-nonacin, squamocin D and asiminecin. The main objective of this study is to report the antifeedant, toxic and nutritional effects of three of those natural acetogenins and their acetylated and methoxy methylated derivatives on Spodoptera frugiperda Smith (Lep-idoptera: Noctuidae). The natural ACGs squamocin and molvizarin killed 100% of S. frugiperda larvae, followed by motrilin (80%). Acetylated derivatives had less toxic and nutritional effects that led to pupal mortality and adult fatal malformations. The addition of MOM derivatives to the larval diet has not toxic effects on larvae, but significantly reduces growth rate and efficiency in conversion of ingested food into biomass, affecting adult survival.

关键词： Acetogenin Annona squamosa Spodoptera frugiperda Acetylated Acetogenin Methoxy Methylated Acetogenin

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Structural Factors of Annonaceous Acetogenins and Their Semisynthetic Analogues Related with the Toxicity on Spodoptera frugiperda

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Journal of Agricultural Chemistry and Environment 2015年第2期4卷 56-61页

作者： Lilian Di Toto Blessing Florencia Budeguer Juan Ramos Alicia Bardón Sonia Diaz Margarita Brovetto Gustavo Seoane adriana neske Instituto de Química Orgánica Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina Instituto de Química Física Facultad de Bioquímica Química y Farmacia Universidad Nacional de Tucumán Ayacucho Argentina INQUINOA-CONICET Tucumán Argentina Dpto de Química Orgánica Fac de Química UdelaR Montevideo Uruguay

Toxic and nutritional effects of annonaceous acetogenins and their semisynthetic analogues on Spodoptera frugiperda were evaluated. Structural modification of the natural ACG, blocking the OH flanking THF with MOM, allowed us to suggest the mode of action of ACG in the membrane. Our study emphasizes the role of the flanking OH and acetyl groups of THF with the membrane hydrophilic polar head groups. They are essential structural factors in the ACG that facilitate the intermolecular interaction that dehydrates the membrane and makes it potentially toxic against Spodoptera frugiperda.

关键词： Annonaceous Acetogenins Polyphagous Lepidopteran Toxicity Nutritional Alterations

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