article · Journal of Agricultural and Food Chemistry
Researchers have designed and synthesised three new series of chemical compounds based on 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines to evaluate their potential as insecticides. Starting from readily accessible precursors, the target molecules were produced in high yields and high purity through reactions with chloro reagents under mild basic conditions. All newly created structures were confirmed using spectral and elemental analytical techniques. The insecticidal activity of the synthesised compounds was tested against both the nymphs and adults of the agricultural pest Aphis gossypii. Screening results revealed that several of the tested substances exhibited promising insecticidal properties. In addition, the functional relationships between molecular structure and biological activity were examined, supported by molecular docking studies on representative compounds.
Aphis gossypii is a widespread pest that threatens agricultural crops. Developing new chemical agents from accessible starting materials supports the search for effective pest management options. Identifying promising molecules and understanding their structure-activity profiles provides foundational knowledge that can assist in designing new crop protection chemicals.
This work is relevant to early-stage agrochemical research aimed at developing new treatments for crop pests such as aphids. Potential commercial users would be pesticide manufacturers and agricultural biotechnology firms exploring new active ingredients. The research is at an early laboratory stage, limited to initial synthesis, computational docking, and preliminary biological screening, meaning significant testing and development would be required before practical use.
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Three new series of 3-(substituted)methylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines were designed and synthesized starting from readily available materials, 7-acetyl-4-cyano-1,6-dimethyl-6-hydroxy-8-(4-pyridyl, 3-pyridyl, phenyl, 4-methoxyphenyl, or 4-chlorophenyl)-5,6,7,8-tetrahydrosoquinoline-3(2<i>H</i>)-thiones <b>2a</b>-<b>e</b> in high yields and very pure states. Thus, compounds <b>2a</b>-<b>e</b> were reacted with some chloro reagents, namely, <i>N</i>-aryl-2-chloroacetamides <b>3a</b>-<b>f</b> and <i>N</i>-(naphthalen-2-yl)-2-chloroacetamide (<b>3g</b>) under mild basic conditions to give the first two series of the target compounds, 3-(<i>N</i>-aryl)carbamoylmethylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>4a</b>-<b>l</b> and <b>5a</b>-<b>e</b>, respectively. Reaction of compounds <b>2d</b>,<b>e</b> with ethyl chloroacetate under the same conditions gave the other series, 3-ethoxycarbonyl-methylthio-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles <b>6d</b>,<b>e</b>. Structural formulas of all of the new compounds were elucidated and confirmed by elemental and spectral analyses. The insecticidal activity of all synthesized 5,6,7,8-tetrahydrosoquinolines toward the nymphs and adults of <i>Aphis gossypii</i> were screened. The results revealed the promising insecticidal activity of some tested compounds. Moreover, the structure-activity relationships as well as molecular docking of some representative compounds were evaluated.
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DOI: 10.1021/acs.jafc.4c03947
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