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The reaction tolerated structurally diverse substrates and proceeded chemo\u2010 and regio\u2010selectively, affording the target compounds in high purity in 5\u201310\u2005minutes. The convenient chromatography\u2010free isolation and purification of the products add practicality to this method. The structural features of the prepared compounds were investigated using dynamic NMR spectroscopy, X\u2010ray crystallography and computational chemistry calculations. X\u2010ray crystallography performed on a representative compound, 3\u2010(7\u2010amino\u20101,2,4\u2010triazolo[1,5\u2010<jats:italic>a<\/jats:italic>][1,3,5]triazin\u20102\u2010yl)\u2010<jats:italic>N<\/jats:italic>\u2010(4\u2010benzyl)propanamide (<jats:bold>4<\/jats:bold>\u2009<jats:bold>l<\/jats:bold>), showed the overall molecular conformation to adopt the shape of the letter C. Notable localisation of \u03c0\u2010electron density is found within the 1,2,4\u2010triazolo[1,5\u2010<jats:italic>a<\/jats:italic>][1,3,5]triazine system; a relatively short C\u2212NH<jats:sub>2<\/jats:sub> bond is consistent with restricted rotation about this bond. This study also presents a detailed analysis of the molecular interactions in <jats:bold>4<\/jats:bold>\u2009<jats:bold>l<\/jats:bold> using DFT and QTAIM methods with a focus on the hydrogen\u2010bonding and \u03c0\u2010stacking interactions that influence the molecular packing of <jats:bold>4<\/jats:bold>\u2009<jats:bold>l<\/jats:bold>. The findings reveal the significant roles of N\u2212H\u22c5O, N\u2212H\u22c5N and C\u2212H\u22c5N interactions, along with electrostatically enhanced \u03c0\u22c5\u03c0 contacts. A broad screening for insecticidal, fungicidal and herbicidal properties identified several compounds with potent herbicidal activity against <jats:italic>Matricaria inodora<\/jats:italic>.<\/jats:p>","DOI":"10.1002\/cplu.202400127","type":"journal-article","created":{"date-parts":[[2024,6,26]],"date-time":"2024-06-26T08:49:01Z","timestamp":1719391741000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["5\u2010Aza\u2010adenine Derivatives for Crop\u2010Protection: Multicomponent Synthesis, Experimental and Theoretical Structural Analysis"],"prefix":"10.1002","volume":"89","author":[{"given":"Lin Yuing","family":"Tan","sequence":"first","affiliation":[{"name":"School of Pharmacy Monash University Malaysia  Jalan Lagoon Selatan Bandar Sunway, Selangor Darul Ehsan 47500 Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Felicia Phei Lin","family":"Lim","sequence":"additional","affiliation":[{"name":"School of Pharmacy Monash University Malaysia  Jalan Lagoon Selatan Bandar Sunway, Selangor Darul Ehsan 47500 Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sheryn","family":"Wong","sequence":"additional","affiliation":[{"name":"School of Pharmacy Monash University Malaysia  Jalan Lagoon Selatan Bandar Sunway, Selangor Darul Ehsan 47500 Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lay Hong","family":"Chuah","sequence":"additional","affiliation":[{"name":"School of Pharmacy Monash University Malaysia  Jalan Lagoon Selatan Bandar Sunway, Selangor Darul Ehsan 47500 Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio","family":"Frontera","sequence":"additional","affiliation":[{"name":"Department of Chemistry Universitat de les Illes Balears  Crta de Valldemossa km 7.5 07122 Palma de Mallorca Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Edward R. 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