Synthesis and Bioactivities of α-Aminophosphonate Derivatives Containing Benzothiazole and Thiourea Moieties

Abstract

The synthesis of a series of novel α-aminophosphonate derivatives containing benzothiazole and thiourea moieties from substituted 2-aminobenzothiazoles and synthetic intermediates O,O′-dialkylisothiocyanat-(phenyl)methylphosphonates under microwave irradiation has been demonstrated. Several salient features, such as good to excellent yields, shorter reaction times, milder reaction conditions, and simple purification procedures, make the present synthetic protocol highly attractive to access the title compounds. Bioassays indicated that most of the compounds possessed broad-spectrum insecticidal and antiviral activities against

Tobacco Mosaic Virus (TMV) in vivo. Interestingly, in comparison with control insecticide Avermectin, two compounds displayed remarkably high in vitro insecticidal activities against Plutella xylostella. Furthermore, according to the results from preliminary bioassay, all were associated with moderate to good anti-TMV activities.

[Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Tables S1–S4. Figures S1–S52.]

GRAPHICAL ABSTRACT

Keywords:

• α-Aminophosphonate derivatives
• thiourea moiety
• benzothiazole moiety
• synthesis
• microwave irradiation
• bioactivity

Acknowledgments

We are grateful for the generous financial support received from National Key Program for Basic Research (Nos. 2010CB126105, 2010CB134504), and National Natural Science Foundation of China (No. 20872021).