以取代氨基吡啶为原料,经二步反应合成关键中间体——取代吡啶基异硫氰酸酯,再分别与4个制各的取代六氢哒嗪中间体缩合,合成了4个系列共22个新型Ⅳ_取代吡啶基-2-酰基四氢哒嗪-1(2H)-硫代甲酰胺类化合物8~11.所有目标产物的结构均经过1HNMR,13CNMR和HRMS的确证.初步的除草活性测试表明,部分化合物在375护ha叫剂量下,对双子叶杂草苘麻及反枝苋和单子叶杂草马唐具有约100%芽前抑制活性.进一步活性筛选发现,2-[(5-氯吡啶-2-基)硫代氨基甲酰基]四氢哒嗪-1(2/4)-甲酸乙酯(9e)在45g·ha-1剂量下对苘麻的抑制率仍达到95%.
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)tetrahydropyridazine-1(2H)-carboxylate (9e) displayed the best pre-emergence herbicidal effect against Abutilon theophrasti with 95% inhibitory activity even at 45 g.ha-1.