Pyrimidinyl-substituted amides and thioureas: syntheses, crystal structure and herbicidal activities |
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| Authors: | Liu Guo-Hua Xue Yun-Ning Lu Xiao-Quan Liu Mou-Ming Wang Wei-Ying Yang Liang-Zhun |
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| Institution: | Department of Chemistry, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, PR China. ghliu@shnu.edu.cn |
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| Abstract: | BACKGROUND: The high herbicidal activities of 1,2,4]triazolo1,5-c]pyrimidine and 2H-1,2,4-thiadiazolo2,3-a]pyrimidine derivatives suggested the development of new fused heterocyclic compounds for application as herbicides. RESULTS: Three series of pyrimidinyl-substituted thioureas (4) and amides (5, 6) were synthesized, and the typical crystal structure of a 2H-1,2,4-thiadiazolo2,3-a]pyrimidine derivative (5a) was determined by X-ray diffraction. All the compounds were tested for herbicidal activity against selected weeds. CONCLUSION: The series of fused heterocyclic amides 5a to 5d exhibited high herbicidal activities both against monocotyledonous weeds (Echinochloa crus-galli L., Sorghum bicolor (L.) M?nch., Digitaria sanguinalis (L.) Scop) and against dicotyledonous weeds (Amaranthus retroflexus L. and Brassica campestris L.) in pre-emergence treatments. In particular, compound 5b at low concentration still showed high inhibitory activity against A. retroflexus in pre-emergence treatment. Different substituents at the meta positions of the pyrimidine ring were found to affect the herbicidal activity. |
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| Keywords: | amide thiourea crystal structure herbicidal activity |
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