Soil biodegradation of a benzoxazinone analog proposed as a natural products-based herbicide
Benzoxazinones with the 4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one skeleton have been proposed as potentially successful models for the development of novel design leads. D-DIBOA has proven to be the most promising base structure in the search for novel herbicide models based on the benzoxazinone skeleton. The biodegradation dynamics of D-DIBOA in soil are therefore relevant and are the subject of this study.
A previously optimized methodology for the assessment of biodegradation has been applied for the first time to a synthetic benzoxazinone.
Biodegradability is a characteristic of natural benzoxazinones and a safety requirement for the development of herbicidal chemicals. The biodegradation phenomenon and its consequences for the development of new herbicide models are discussed. The half-life determined for D-DIBOA was much higher than those previously reported for the natural products DIBOA, DIMBOA and their benzoxazolinone derivatives.
This finding, together with its previously described potent phytotoxicity, suggests that D-DIBOA is a useful candidate for novel herbicide model development. The lactam D-HBOA, which is slightly less phytotoxic than its precursor, was discovered to be the first and principal metabolite resulting from D-DIBOA degradation.
KeywordsD-DIBOA Benzoxazinones Degradation study Soil Herbicide models
This research was supported by the Ministerio de Economía y Competitividad (MINECO), Spain (Project AGL2013-42238-R) and Consejería de Innovación, Ciencia e Industria, Junta de Andalucía, Spain (Project DP12-TEP-725).
Conflict of interest
The authors declare no conflict of interest associated with this manuscript.
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