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Synthesis of benzohydroxamic acids, their degradation products and derivatives

The analysis, bioactivity evaluation and determination of fate and toxicity of wheat allelochemicals and their main degradation products needs useful protocols for their synthetic obtaining up to the multigram scale. Thus, several methodologies including optimisations from previously reported works, and new procedures have been developed in order to get amounts of the compounds enough for all of these purposes.

The optimised synthetic methodologies have yielded compounds belonging to three different structural families: benzoxazinones, hydroxyphenylmalonamic acids and aminophenoxazinones that derive from natural allelochemicals DIMBOA and DIBOA. Benzoxazinones have been obtained from synthetic methods optimised from literature. These procedures have been modified with the intention of increasing reaction yields and obtaining starting materials of diverse structure, in order to get new leads to the development of new herbicide models based on their structures. Several of these compounds have been used as chemical standards in the development of analytical procedures towards the determination of soil degradation dynamics of allelochemicals.

Hydroxyphenylmalonamic acids are fungal detoxification products from allelochemicals DIMBOA and DIBOA. Their synthesis has been developed in order to have enough amounts for their bioactivity evaluation, and to discover their ecological role. Aminophenoxazinones have been synthesized in order to determine their presence and concentration in soil after the release of allelochemicals DIMBOA and DIBOA by plants. Their bioactivity evaluation is an interesting research topic since these compounds could important to understand the allelopathic behaviour of plants that produce high amounts of benzohydroxamic acids. New synthetic procedures have been developed to get access to some derivatives in large scale.

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