Soy polyol formulations as novel seed treatments for the management of soil-borne diseases of soybean.

Polyurethanes prepared from vegetable oils display a number of desirable properties useful for many commercial and industrial applications. One unique application is that of an agricultural seed treatment. Seed treatments are used to incorporate pesticides onto the seed coat and to decrease the disease susceptibility of the seed during its germination in the soil. In addition, by altering the movement of water across the seed coat and by incorporating protective pesticides in the coating, seed coating polymers can enhance the germination and survival of the seed under adverse environmental conditions. Soy polyols alone, and in combination with glycerin, polymerized with 4,4'-diphenylmethane diisocyanate (MDI) were studied for their seed treating properties and impact on soybean seed germination. The cross-linking density and properties of these polyurethane compounds were varied by changing the isocyanate/hydroxyl molar ratios. In order to optimize the coating qualities and to increase the efficiency of the coating, acetone was also studied as a diluting solvent to reduce the viscosity of the polyurethane mixture prior to polymerization on the seed coat. Optimal polymerization and resulting germination (95%) were obtained using a 1:1 isocyanate/hydroxyl molar ratio consisting of a mixture of soy polyol 180 and glycerin, and the use of an equal volume of acetone as a dilution solvent. This optimal polyurethane seed treatment had several desirable qualities including: reduced viscosity, decreased seed coating thickness, increased seed coating uniformity and permitted larger volumes of seed to be treated with the same volume of polymer. This optimal seed treatment increased the soybean seed germination by 15%, as compared with untreated seed. In addition, preliminary studies of the compatibility of these unique formulations with commercial and experimental fungicides also support the use of these polymers as seed treatments due to their enhanced stability, longevity and slow active ingredient water teaching characteristics. Compatibility of these seed coating polymers as formulations with captan, metalaxyl, thiabendazole and novel antimicrobial lipids and triterpenoid compounds display that the active ingredients can readily provide a zone of fungal inhibition around the seed as it germinates in the presence of Macrophomina phaseolino, causal agent of charcoal rot of soybeans. However, the release of the active ingredient from the polyol seed treatments is less affected by water leaching as compared to commercially available water-soluble seed treating polymer formulations. This is most likely due to the polyols unique polymer cross-linking characteristics. These results support the continued exploration of soy polyol derived polymers as seed coating compounds.

Evaluation of coumarin derivatives as anti-fungal agents against soil-borne fungal pathogens.

Development of new and safer pesticides that are target-specific is backed by a strong Federal, public and commercial mandate. In order to generate a new generation of pesticides that are more ecologically friendly and safe, natural products are being evaluated for pesticidal activities. Many plant-derived chemicals have proven pesticidal properties, including compounds like sesamol (3,4-Methylenedioxyphenol), a lipid from sesame oil and coumarins (1,2-Benzopyrone) found in a variety of plants such as clover, sweet woodruff and grasses. Both of these plant-derived compounds have been shown to inhibit a range of fungi and bacteria and it is believed that these cyclic compounds behave as natural pesticidal defense molecules for plants. These compounds represent a starting point for the exploration of new derivative compounds possessing a range of antifungal activity and for use as seed protectants. Within this study, six derivatives of coumarin that resembled sesamol's structure were screened for their antifungal activity against a range of soil-bome plant pathogenic fungi. Fungi in this in vitro screen included Macrophomina phaseolina (causal agent of charcoal rot) and Pythium spp. (causal agent of seedling blight), two phylogenetically diverse and economically important plant pathogens. Preliminary studies indicate that many of these novel coumarin derivatives work very effectively in vitro to inhibit fungal growth and several coumarin derivatives have higher antifungal activity and stability as compared to either the original coumarin or sesamol compounds alone. Interestingly, several of these highly active coumarin derivatives are halogenated compounds with solubility in water, and they are relatively easy and inexpensive to synthesize. These halogenated coumarin derivatives remained active for extended periods of time displaying 100% inhibition of fungal growth for greater than 3 weeks in vitro. In addition to the in vitro fungal inhibition assays, preliminary phytotoxicity assays of these halogenated coumarin compounds show no obvious plant toxicity issues or interference in plant development. These results support additional research in this area of natural pesticide development.

Field assessment of plant derivative compounds for managing fungal soybean diseases.

Natural plant-derived compounds are currently being explored as alternatives for pest control in sustainable agriculture. This study explored the use of two compounds, sesamol and carbenoxolone, in the management of the fungal soybean disease charcoal rot (Macrophomina phaseolina). Previous studies have determined that sesamol and carbenoxolone compounds significantly inhibited fungal pathogen growth and plant disease in vitro. In order to assess the field efficacy of these compounds for fungal disease control, 2 years of field testing of these compounds have been conducted in southeast Kansas. Field treatments of the compounds sesamol and carbenoxolone at three concentrations, 0, 500 and 1000 microg/ml, were applied foliarly at four distinct plant developmental stages. Treatments were applied to plots in random triplicate array and the experiment was repeated during the 1998 and 1999 growing seasons. Disease assessments were based on visual disease ratings, plant mortality and soybean yield analysis. Data were recorded weekly for each treatment plot and statistically analysed using analysis of variance. Results indicate that sesamol and carbenoxolone treatments significantly decreased disease symptoms (11-12%) and plant mortality (24-28%) while significantly increasing soybean yields (18-38%). These results support that plant-derived compounds can have a significant impact on soybean disease management and yield under field conditions.