Solvent-Free Synthesis and Safener Activity of Sulfonylurea Benzothiazolines.

Ying Fu,Li-Xia Zhao,Yu-Feng Chen,Jing-Yi Wang,Dong Zhang,Shuang Gao,Fei Ye

doi:10.3390/molecules22101601

Ying Fu, Li-Xia Zhao + Show 5 more

Open Access

https://doi.org/10.3390/molecules22101601

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Abstract

A series of novel sulfonylurea benzothiazolines was designed by splicing active groups and bioisosterism. A solvent-free synthetic route was developed for the sulfonylurea benzothiazoline derivatives via the cyclization and carbamylation. All compounds were characterized by IR, 1H-NMR, 13C-NMR, HRMS. The biological activity tests indicated the compounds could protect maize against the injury caused by chlorsulfuron to some extent. The molecular docking result showed that the new compound competed with chlorsulfuron to bind with the herbicide target enzyme active site to attain detoxification.

Highlights

IntroductionSulfur and nitrogen-containing heterocyclic compounds play a key role pharmaceutical
Sulfur and nitrogen-containing heterocyclic compounds play a key role pharmaceuticalSulfur and nitrogen-containing heterocyclic compounds play a key role in in thethe pharmaceutical and chemical industries [1,2].In particular, sulfur-containing heterocyclic compounds areare widely used and chemical industries [1,2]
1,3-Benzothiazoline derivatives 2 were synthesized with o-aminothiophenol and ketone 1 smoothly

Summary

Introduction

Sulfur and nitrogen-containing heterocyclic compounds play a key role pharmaceutical. Compounds are reported to be herbicide shows good sterilization and anti-corrosion performance. New triketone derivatives with better herbicidal activity have been designed splicing active group alloxydim-sodium into quizalofop-ethyl Herbicides and safeners may share common molecular characteristics, depending onofthe structure-activity relationships (SAR). Sulfamide compounds may bebe structural features between herbicides and safeners. Sulfamide compounds may be an antidote to protect plants from the injury caused by sulfonylurea herbicides. In view of the facts mentioned above, a series of novel sulfonylurea benzothiazoline was designed and synthesized with o-aminothiophenol and ketone as starting materials in the presence designed and synthesized with o-aminothiophenol and ketone as starting materials in the presence of and synthesized with o-aminothiophenol and of designed neutral alumina via a solvent-free procedure

Chemistry

Biological Activity

Chlorsulfuronand and3c

Reagents and Analysis

Conclusions