从2-取代-4.5-二氯哒嗪酮(1)出发,使2-取代-4-氯-5-羟基哒嗪酮(2)与溴乙基氨基甲酸酯反应合成含哒嗪酮的氨基甲酸酯类化合物(5a,5b).将化合物1与乙醇胺反应制得2-取代-4-氯-5-(2-氨基乙氧)哒嗪酮(3),化合物3与氯甲酸酯反应得到5a~51.化合物3催化加氢生成2-取代-5-(2-氨基乙氧)哒嗪酮(4).化合物4与氯甲酸酯在-10~-5℃反应得到化合物(6a~6d),在0~15 C反应得到相应N,N-二甲酸酯化合物(7a,7b).探讨了中间体3与4的反应活性.生物活性测试结果表明其中一些化合物具有较好的杀菌活性.
Pyridazinone-carbamate derivatives 5a~51 were synthesized starting from 2-substituted4,5-dichloro pyridazinones 1 via two routes. One is that 2-substituted-4-chloro-5-hydroxyl pyridazinones 2 reacted with β-bromoethyl carbamates to afford compounds 5a and 5b. The other is that 2-substituted-4-chloro-5-(2-amino ethyloxyl)pyridazinones 3 obtained from the reaction of 1 with amino ethanol, reacted with chloroformate to give 5a~51. Furthermore, the catalytic hydrogenation of 3 gave 2-substituted-5-(2-amino ethyloxyl)pyridazinones 4, which reacted with chloromates to produce compounds 6a~6d at temperatures between -10~-5 C, and to N,N-dicarbamates 7a and 7b at 0~15 C. The reactivity of intermidiates 3 and 4 was also discussed. The preliminary bioassay indicated that almost all of the compounds showed fungicidal activities.
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