CN103159752A - N-吡啶基取代噻唑甲酰胺类化合物的制备及杀菌活性 - Google Patents
N-吡啶基取代噻唑甲酰胺类化合物的制备及杀菌活性 Download PDFInfo
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Abstract
本发明公开了N-吡啶基取代噻唑甲酰胺类化合物a-e的制备及杀菌活性。所述的N-吡啶基取代噻唑甲酰胺类化合物是由2-甲基-4-三氟甲基噻唑甲酰氯和取代氨基吡啶合成的。对所述的N-吡啶基取代噻唑甲酰胺类化合物进行杀菌活性测试,结果表明:目标化合物对于水稻纹枯病菌均表现出较好的抑制活性,其中表现最好的化合物a在质量浓度500mg/L下抑制率达到91.78%。
Description
技术领域
本发明涉及N-吡啶基取代噻唑甲酰胺类化合物的制备方法及杀菌活性,属于一类可作为杀菌剂的新农药。
背景技术
近年来,新开发的农药品种有80%都是杂环化合物,其中以含氮杂环最为重要。噻唑类化合物因其良好的生物活性和高效低毒的特点受到了广泛的研究,而吡啶类化合物在农药方面的应用也从上世纪八十年代后迅速增加。但是噻唑吡啶类化合物还未见报道。为了寻找活性更好的高效低毒的广谱杀菌剂,选取2-甲基-4-三氟甲基噻唑甲酰氯和取代氨基吡啶合成了化合物a-e。
发明内容
本发明的目的在于公开N-吡啶基取代噻唑甲酰胺类化合物a-e的制备方法及杀菌活性。
本发明所述的N-吡啶基取代噻唑甲酰胺类化合物是通过以下方法制备合成的,其特征在于包括以下过程:三口瓶中加入0.01mol的2-甲基-4-三氟甲基噻唑甲酰氯,甲苯30ml,0.01mol的取代氨基吡啶,0.01g三乙胺,加热至回流,反应8小时,蒸发除去溶剂,加水20ml搅拌30min,水相用乙酸乙酯萃取,有机相用10%NaHCO3,水,盐水洗涤,旋干得到粗产品,将所得固体用重结晶或者柱层析等方法分离得到目标化合物a-e。化合物a-e均为白色或灰色粉末。
本发明所述的N-吡啶基取代噻唑甲酰胺类化合物的杀菌活性是通过以下方法测定的:参照中华人民共和国农业部编写的《农药室内生物测定试验准则》中的方法NY/T1156.2-2006进行。采用含药马铃薯琼脂培养基法(PDA)测试了目标化合物对:D:花生褐斑peanut brown spot(Cercospora rachidicola);F:番茄早疫tomato early blight(Alternaria solani);G:小麦赤霉Wheat head Scab(Gibberella zeae);I:苹果轮纹AppleRing rot(Physalospora piricola);L:黄瓜灰霉病菌cucumber gray mold(Botrytiscinerea);N:油菜菌核病菌rape sclerotiniose(Sclerotinia sclerotiorum);Rc:禾谷丝核菌Rhizoctonia cerealis;T:水稻纹枯病菌rice sheath blight(Pellicularia sasakii)的活性。以噻呋酰胺(thifluzamide,95%原药)为对照药剂,另设空白对照(CK)。药剂配制方法:准确称取2mg样品,先用0.2mL N,N-二甲基甲酰胺(DMF)溶解,再加入含质量分数为0.1%吐温-80的无菌水3.8mL,搅拌均匀,配制成500mg/L的药液备用。
对所述的N-吡啶基取代噻唑甲酰胺类化合物进行抑菌活性测试,结果(见表1)表明,在质量浓度500mg/L下,五个目标化合物a-e对禾谷丝核菌和水稻纹枯病菌均表现出一定的抑制活性,其中对水稻纹枯病菌的抑制率明显高于对其他病菌的抑制率,其中化合物a,c,d,e对其的抑制率均在80%以上,并且其中表现最好的化合物a在质量浓度500mg/L下抑制率达到了91.78%。
表1目标化合物的抑菌活性(抑制率,%)
注:D:花生褐斑peanut brown spot(Cercospora rachidicola)F:番茄早疫tomato early blight(Alternaria solani)G:小麦赤霉Wheat head Scab(Gibberella zeae)I:苹果轮纹Apple Ring rot(Physalospora piricola)L:黄瓜灰霉病菌cucumber gray mold(Botrytis cinerea)N:油菜菌核病菌rape sclerotiniose(Sclerotinia sclerotiorum)Rc:禾谷丝核菌Rhizoctonia cerealis T:水稻纹枯病菌rice sheath blight(Pellicularia sasakii)
下面通过具体实施方式对本发明作进一步说明,但并不意味着对本发明保护范围的限制。
具体实施方式
实施例1
三口瓶中加入0.01mol的2-甲基-4-三氟甲基噻唑甲酰氯,甲苯30ml,0.01mol的3-氯-5-三氟甲基-2-氨基吡啶,0.01g三乙胺,加热至回流,反应8小时,蒸发除去溶剂,加水20ml搅拌30min,水相用乙酸乙酯萃取,有机相用10%NaHCO3,水,盐水洗涤,旋干得到粗产品,将所得固体用重结晶方法分离得到目标化合物a,收率为73.5%。化合物a为白色固体粉末。熔点:128-129℃。MS:390.2(m/z,M+1)。1H NMR(500MHz,CDCl3):2.786(s,3H,CH3),8.005-8.009(d,1H,Py-H),8.592(s.1H,Py-H),8.613(s,1H,NH)。
实施例2
三口瓶中加入0.01mol的2-甲基-4-三氟甲基噻唑甲酰氯,甲苯30ml,0.01mol的3-氯-2-氨基吡啶,0.01g三乙胺,加热至回流,反应8小时,蒸发除去溶剂,加水20ml搅拌30min,水相用乙酸乙酯萃取,有机相用10%NaHCO3,水,盐水洗涤,旋干得到粗产品,将所得固体用重结晶方法分离得到目标化合物c,收率为68.4%。化合物c为白色固体粉末。熔点:133-134℃。MS:322.1(m/z,M+1)。1H NMR(500MHz,CDCl3):2.770(s,3H,CH3),7.128-7.154(m,1H,Py-H),7.786-7.806(m,1H,Py-H),8.327-8.335(m,1H,Py-H),9.499(s,1H,NH)。
实施例3
三口瓶中加入0.01mol的2-甲基-4-三氟甲基噻唑甲酰氯,甲苯30ml,0.01mol的4-氯-2-氨基吡啶,0.01g三乙胺,加热至回流,反应8小时,蒸发除去溶剂,加水20ml搅拌30min,水相用乙酸乙酯萃取,有机相用10%NaHCO3,水,盐水洗涤,旋干得到粗产品,将所得固体用柱层析方法分离得到目标化合物d,收率为72.5%。化合物d为灰色固体粉末。熔点:186-187℃。MS:322.2(m/z,M+1)。1H NMR(500MHz,CDCl3):2.758(s,3H,CH3),7.064-7.089(m,1H,Py-H),7.753-7.787(m,1H,Py-H),8.048-8.058(d,1H,Py-H),8.247-8.264(d,1H,Py-H),9.487(s,1H,NH)。
Claims (3)
2.按权利要求1所述的N-吡啶基取代噻唑甲酰胺类化合物,其特征在于:所述的N-吡啶基取代噻唑甲酰胺类化合物是由2-甲基-4-三氟甲基噻唑甲酰氯和取代氨基吡啶合成的。
3.按权利要求2所述的N-吡啶基取代噻唑甲酰胺类化合物,其特征在于:对所述的N-吡啶基取代噻唑甲酰胺类化合物进行抑菌活性测试,结果表明,在质量浓度500mg/L下,五个目标化合物a-e对禾谷丝核菌和水稻纹枯病菌均表现出一定的抑制活性,其中对水稻纹枯病菌的抑制率明显高于对其他病菌的抑制率,其中化合物a,c,d,e对其的抑制率均在80%以上,并且其中表现最好的化合物a在质量浓度500mg/L下抑制率达到了91.78%。
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CN109422704A (zh) * | 2018-11-26 | 2019-03-05 | 南开大学 | 一类4位取代噻唑酰胺衍生物及其制备方法和用途 |
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US5045554A (en) * | 1988-11-29 | 1991-09-03 | Monsanto Company | Substituted thiazoles and their use as fungicides |
CN1927838A (zh) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | N-(取代的吡啶)酰胺类化合物及其制备与应用 |
CN101550113A (zh) * | 2008-04-03 | 2009-10-07 | 上海药明康德新药开发有限公司 | 由2-溴噻唑一锅法合成噻唑-2-甲酰胺的工业化制备方法 |
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US3725427A (en) * | 1966-12-07 | 1973-04-03 | Uniroyal Ltd | Certain 2,4-dimethyl-5-carboxamido-thiazoles |
US5045554A (en) * | 1988-11-29 | 1991-09-03 | Monsanto Company | Substituted thiazoles and their use as fungicides |
CN1927838A (zh) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | N-(取代的吡啶)酰胺类化合物及其制备与应用 |
CN101550113A (zh) * | 2008-04-03 | 2009-10-07 | 上海药明康德新药开发有限公司 | 由2-溴噻唑一锅法合成噻唑-2-甲酰胺的工业化制备方法 |
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