Insecticidal and Nematicidal Activities of Novel Mimosine Derivatives.

Binh Nguyen,Shinkichi Tawata,Jamnian Chompoo

doi:10.3390/molecules200916741

Binh Nguyen, Shinkichi Tawata + Show 1 more

Open Access

https://doi.org/10.3390/molecules200916741

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Abstract

Mimosine, a non-protein amino acid, is found in several tropical and subtropical plants, which has high value for medicine and agricultural chemicals. Here, in continuation of works aimed to development of natural product-based pesticidal agents, we present the first significant findings for insecticidal and nematicidal activities of novel mimosine derivatives. Interestingly, mimosinol and deuterated mimosinol (d-mimosinol) from mimosine had strong insecticidal activity which could be a result of tyrosinase inhibition (IC50 = 31.4 and 46.1 μM, respectively). Of synthesized phosphoramidothionate derivatives from two these amino alcohols, two compounds (1a and 1b) showed high insecticidal activity (LD50 = 0.5 and 0.7 μg/insect, respectively) with 50%–60% mortality at 50 μg/mL which may be attributed to acetylcholinesterase inhibition. Compounds 1a and 1b also had strong nematicidal activity with IC50 = 31.8 and 50.2 μM, respectively. Our results suggest that the length of the alkyl chain and the functional group at the C5-position of phosphoramidothionates derived from mimosinol and d-mimosinol are essential for the insecticidal and nematicidal activities. These results reveal an unexplored scaffold as new insecticide and nematicide.

Highlights

Organophosphorus compounds are a highly diverse class of organic chemicals with many uses [1], and form one of the most important groups of modern pesticides [2]
In this study, using mimosine as starting material, we identified insecticidal activity in amino alcohols derived from mimosine, and we synthesized a family of five-membered cyclic phosphoramidothionate derivatives from these alcohols to assess their insecticidal and nematicidal activities
We describe a route for synthesis of amino alcohols and their phosphoramidothionates from mimosine

Summary

Introduction

Organophosphorus compounds are a highly diverse class of organic chemicals with many uses [1], and form one of the most important groups of modern pesticides [2]. The advantageous properties of phosphorus compounds are a result of their relatively low stability, their decomposition to products that are not toxic to humans and animals, and their low rate of use per unit treated area [3]. Another important feature of these compounds is that their action is highly selective [4]. Utilization of organophosphorus pesticides is favored over organochlorine compounds because of their ability to degrade more readily in the environment [5] Overuse of these compounds can lead to the development of resistance in pests [6]. Pest resistance has led to the need for development of new non-persistent and non-toxic pesticides with selective activity to help maintain stable food production

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