CN102775373A - 一种n-取代氨基香豆素类化合物及其制备与应用 - Google Patents
一种n-取代氨基香豆素类化合物及其制备与应用 Download PDFInfo
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Abstract
本发明一种N-取代氨基香豆素类化合物及其制备与应用，涉及一种氨基香豆素类化合物及其制备方法，以及在农业病害及草害防治上的应用。该化合物可通过2步反应制备：6-氨基香豆素与取代苯甲醛缩合物经还原得中间体，中间体再与卤代烃（或酰卤）在有机碱催化下制得目的化合物，它对葡萄白腐病菌、苹果腐烂病菌、棉花枯萎病菌、柑橘炭疽病菌等多种农业植物病原菌具有优异的抑菌活性，同时对反枝苋及稗草等杂草的生长也有一定抑制作用。
Description
技术领域
本发明为一种N-取代氨基香豆素类化合物及其制备与应用，具体的涉及农用杀菌及除草剂领域。
背景技术
天然产物香豆素和酰基芳胺类化合物均是已知的具有生物活性的化合物，该专利涉及化合物中既有香豆素的结构，又有酰基芳胺的结构，是一种具有优异农药活性的新化合物。
发明内容
本发明的目的在于提供一种新的N-取代氨基香豆素类化合物及其制备方法，它可应用于农业上以防治作物的病害及草害。
本发明的技术方案如下：
本发明提供一种N-取代氨基香豆素类化合物，其结构通式如下：
R1选自氢、C1-C12烷基、C2-C12烯基、C2-C12炔基、C1-C12卤代烷基、C1-C12烷基羰基、C1-C12卤代烷基羰基、C1-C12烷磺酰基、C1-C12烷氧基羰基；R2选自氢、卤素、羟基、氰基、硝基、C1-C12烷基、C2-C12烯基、C2-C12炔基、C1-C12卤代烷基、C1-C12烷氧基、C1-C12烷硫基、C1-C12烷基羰基、C1-C12卤代烷基羰基、C1-C12烷磺酰基、C1-C12烷氧基羰基中的一到五个；及其异构体。
其中，当R1为氢或甲基时，R2不为氢或邻溴。
反应式
式中R1、R2定义如上，Z是离去基团，如卤素（氯、溴、碘）
通式化合物可以这样来制备：在适当溶剂中，Ⅴ和Ⅳ缩合产物用硼氢化钠（或氰基硼氢化钠）还原得化合物Ⅲ，然后加入化合物Ⅱ，在适当温度下，以适当碱催化反应一定时间后，处理即得目的产物。
适当溶剂可选自苯、甲苯、二甲苯、二氯甲烷、氯仿、四氢呋喃、乙酸乙酯、丙酮、乙腈、乙醇、甲醇等。
适当温度指室温至溶剂的沸点温度，通常为20-100 ℃。
适当碱可选自碳酸钠、碳酸氢钠、碳酸钾、醋酸钠、三乙胺、吡啶、哌啶等
反应时间为30分钟至20小时。
本发明的化合物对多种农业植物病原菌及杂草等有很好的抑制或杀伤作用。
具体实施方式
化合物的典型制备：
实例1
将0.16g（1mmol）6-氨基香豆素和0.14g（1.1mmol）对氟苯甲醛加入干燥甲苯中，加热回流5h。分批加入硼氢化钠0.06g（1.5 mmol），反应4h。浓缩除去溶剂，加入20ml蒸馏水，搅拌10min，用二氯甲烷萃取3次，有机相用无水硫酸钠干燥，浓缩得中间产物。
将0.27g（1mmol）中间产物和0.10g（1.1mmol）丙酰氯溶于乙腈，滴加3滴三乙胺，加热至50℃，搅拌反应8h，减压浓缩除去溶剂得目的化合物。
核磁数据（1HNMR, 300MHz；内标TMS；溶剂CD3Cl）如下：
δppm 7.36(1H, d), 7.11-6.95(5H,m), 6.85(2H,t), 6.12(1H, d), 4.64(2H,s), 2.27(2H,q), 1.14(3H,t)；
农药活性典型测定：
实例2 抑菌活性测定
取一定量实例1化合物用丙酮溶解并定容得供试药液，将该药液适量置于100 ml 60℃左右PDA灭菌培养基中，摇匀，倒入直径60 mm的灭菌培养皿中，冷却凝固后，分别移接生长一致、直径为4 mm的菌饼，以加入等量丙酮的灭菌培养基作为空白对照，每处理设3次重复。放入25℃恒温培养箱中培养一定时间后，测量菌落直径，计算抑菌率，求取有效中浓度EC50。如：对苹果腐烂病菌的EC50为17.0ppm，对葡萄白腐病菌的EC50为14.9ppm，对棉花枯萎病菌的EC50为24.2ppm，对柑橘炭疽病菌的EC50为12.9ppm。
实例3 除草活性测定
取一定量下列实例化合物用丙酮溶解并定容得供试药液。在培养皿（d=9 cm）中铺两层滤纸，准确加入供试药液1.0 ml，对照加丙酮1.0 ml，待丙酮挥发干后，加入蒸馏水5 ml，再将10粒供试植物种子在滤纸上摆成一行，所有处理重复3次，置于25±1 ℃温室中培养，期间适时补充水分，3～7d后（依据种子萌发及幼苗生长速度）测量种子主根（最长根）及芽长，计算根、芽生长抑制率。如：对反枝苋种子幼根的EC50为13.8ppm，对稗草种子幼根的EC50为21.4ppm。
Claims (4)
1.一种N-取代氨基香豆素类化合物，如通式所示：
R1选自氢、C1-C12烷基、C2-C12烯基、C2-C12炔基、C1-C12卤代烷基、C1-C12烷基羰基、C1-C12卤代烷基羰基、C1-C12烷磺酰基、C1-C12烷氧基羰基；R2选自氢、卤素、羟基、氰基、硝基、C1-C12烷基、C2-C12烯基、C2-C12炔基、C1-C12卤代烷基、C1-C12烷氧基、C1-C12烷硫基、C1-C12烷基羰基、C1-C12卤代烷基羰基、C1-C12烷磺酰基、C1-C12烷氧基羰基中的一到五个；及其异构体；
其中，当R1为氢或甲基时，R2不为氢或邻溴。
2.权利要求1所述的化合物可通过下列反应制备：
式中R1、R2定义如上，Z是离去基团，如卤素（氯、溴、碘）。
3.权利要求1所述的化合物在防治作物病害上的应用。
4.权利要求1所述的化合物在防治作物草害上的应用。
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592183A (zh) * | 2015-01-15 | 2015-05-06 | 青岛农业大学 | N-酰基-n-间氟苄基-8-氨基香豆素类化合物及其制备与除草用途 |
| CN105218530A (zh) * | 2015-10-20 | 2016-01-06 | 青岛农业大学 | 3-(1-芳基-2-(2-氮杂芳烃)乙基)-4-羟基香豆素及其制备方法 |
| CN106967028A (zh) * | 2017-04-07 | 2017-07-21 | 青岛农业大学 | 一类新型含氟酰胺基香豆素化合物及其制备与除草用途 |
| CN108017607A (zh) * | 2017-12-11 | 2018-05-11 | 青岛农业大学 | 一类新型n-取代胺基香豆素及其除草与杀菌用途 |
| CN111169045A (zh) * | 2020-01-07 | 2020-05-19 | 北玻院(滕州)复合材料有限公司 | 风电叶片主梁片材拉挤成型浸胶装置、模具、设备及方法 |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104592183A (zh) * | 2015-01-15 | 2015-05-06 | 青岛农业大学 | N-酰基-n-间氟苄基-8-氨基香豆素类化合物及其制备与除草用途 |
| CN105218530A (zh) * | 2015-10-20 | 2016-01-06 | 青岛农业大学 | 3-(1-芳基-2-(2-氮杂芳烃)乙基)-4-羟基香豆素及其制备方法 |
| CN105218530B (zh) * | 2015-10-20 | 2019-07-02 | 青岛农业大学 | 3-(1-芳基-2-(2-氮杂芳烃)乙基)-4-羟基香豆素及其制备方法 |
| CN106967028A (zh) * | 2017-04-07 | 2017-07-21 | 青岛农业大学 | 一类新型含氟酰胺基香豆素化合物及其制备与除草用途 |
| CN106967028B (zh) * | 2017-04-07 | 2019-08-30 | 青岛农业大学 | 一类含氟酰胺基香豆素化合物及其制备与除草用途 |
| CN108017607A (zh) * | 2017-12-11 | 2018-05-11 | 青岛农业大学 | 一类新型n-取代胺基香豆素及其除草与杀菌用途 |
| CN108017607B (zh) * | 2017-12-11 | 2019-10-29 | 青岛农业大学 | 一类n-取代胺基香豆素及其除草与杀菌用途 |
| CN111169045A (zh) * | 2020-01-07 | 2020-05-19 | 北玻院(滕州)复合材料有限公司 | 风电叶片主梁片材拉挤成型浸胶装置、模具、设备及方法 |
| CN111169045B (zh) * | 2020-01-07 | 2022-06-21 | 北玻院(滕州)复合材料有限公司 | 风电叶片主梁片材拉挤成型浸胶装置、模具、设备及方法 |
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