Weed interference is one of the most significant yield-limiting factors which can cause a significant economic loss on the global agricultural industry. Hence, over the past decades weed management by utilizing herbicides has become a vital aspect of modern agriculture for managing unwanted foliage. However, the extended number of resistant weeds and overall environmental effects have become a great concern in this trend. Although some currently available herbicides are designed to kill only unwanted foliage with less toxicity to humans, they are still have extreme consequences in the environment. Therefore, natural herbicides could be a safe alternative for weed control. Along these lines, Thaxtomin A (TA) is a naturally occurring alkaloid, isolated from a Gram-positive soil bacteria, Streptomyces scabies, which contains a cyclic dipeptide or 2,5-diketopiperazine core. TA is able to induce terminal potato scab disease, causes a significant economic loss on the global potato agricultural industry. It can also control the germination and growth of weeds in cereal crops with no effects on the desired plants, and it is also active at very low concentrations. Moreover, this powerful weed-killer has the advantage of being biodegradable. Therefore, due to non-toxicity, high selectivity, biodegradability and predominant activity, TA becomes a significant herbicide candidate which can compete with other commercial herbicides like dichlobenil and isoxaben. Several companies hold patents for the exploitation of this molecule but marketing TA has not been very profitable due to high production costs. Our group has previously reported on the total synthesis of TA via a one-pot Ugi reaction as an alternative approach for rapid production. Although TA has been introduced as a powerful herbicide, there are known TA resistant weed species call TXR1 mutants such as that belonging to Arabidopsis thaliana that TA is ineffective against. Therefore, finding more potent herbicides mimicking TA characteristics has encouraged us to make libraries of TA derivatives.

Synthesis and evaluation of natural herbicide, Thaxtomin A and analogous

253rd National Meeting (2017)

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