Chinese Journal of Organic Chemistry >
Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2- acyltetrahydropyridazine-1(2H)-carbothioamides
Received date: 2015-01-29
Revised date: 2015-02-28
Online published: 2015-07-24
Supported by
Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03), and the National Natural Science Foundation of China (No. 21172256).
Key intermediates-substituted pyridyl isothiocyanates, which were prepared from starting material substituted pyridyl amines via two steps, were further condensed with four substituted hexahydropyridazine intermediates to afford four series of novel N-substituted pyridyl-2-acyltetrahydropyridazine-1(2H)-carbothioamides 8～11. The structures of all compounds have been confirmed by 1H NMR, 13C NMR and HRMS techniques. The preliminary bioassay results indicated that some of the title compounds exhibited approximately 100% inhibition against Abutilon theophrasti, Amaranthus retroflexus and Digitaria sanguinalis at a dose of 375 g·ha-1. In particular, ethyl 2-((5-chloropyridin-2-yl)carbamothioyl)tetrahydropy- ridazine-1(2H)-carboxylate (9e) displayed the best pre-emergence herbicidal effect against Abutilon theophrasti with 95% inhibitory activity even at 45 g·ha-1.
Zhang Hao , Liu Ruiquan , Li Qibo , Li Qingyang , Chen Yahong , Liu Kechang , Liu Shangzhong . Synthesis and Herbicidal Activities of N-Substituted Pyridyl-2- acyltetrahydropyridazine-1(2H)-carbothioamides[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1506 -1513 . DOI: 10.6023/cjoc201501040
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