CN108623531A - 一种邻氨基苯甲酰胺类植物生长调节剂 - Google Patents
一种邻氨基苯甲酰胺类植物生长调节剂 Download PDFInfo
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- A—HUMAN NECESSITIES
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Abstract
本发明公开了一种邻氨基苯甲酰胺类化合物，结构如通式I所示：式中R为：
Description
技术领域 本发明属于农用植物生长调节剂领域，具体涉及一种邻氨基苯甲酰胺类植物生长调节剂。
背景技术 植物生长调节剂作为植物化学控制手段在农作物增产、早熟、改善品质及抗逆等方面取得了广泛应用。病虫害防治也是增产的方向之一，在农作物和蔬菜侵染性病害中，主要有真菌性病害和细菌性病害，真菌性病害对农作物的危害最大，甚至能够导致大幅度的减产。在现有技术中，如本发明所述的具有高细胞分裂活性和杀菌活性的一种邻氨基苯甲酰胺类植物生长调节剂未见公开。
发明内容 本发明的目的是提供一种兼具细胞分裂活性和杀菌活性的一种邻氨基苯甲酰胺类植物生长调节剂，可用于农作物的增产提质。
本发明的技术方案如下：
一种邻氨基苯甲酰胺类化合物，结构如通式I所示：
式中R为：
式I化合物可由靛红酸酐和取代胺反应制备，反应式如下：
R的定义同上。
具体制备方法见本说明书合成实例。
本发明化合物在作为植物生长调节剂使用时，可单独使用，也可与其他活性物质组合使用，以提高产品的综合性能。
本发明还包括式I化合物作为活性组分的植物生长调节剂组合物，该组合物中包括式I化合物作为活性组分以及农业上可接受的载体。
本发明还包括式I化合物作为杀菌剂活性组分，可以单独使用，也可以与其它杀菌剂及其他活性物质组合使用，以便提高产品的综合功能。该杀菌剂组合物中还包括农业或林业上可接受的载体。
本发明的化合物可以制剂的形式施用，式I化合物作为活性组分溶解或分散于载体中配制成微乳剂、水乳剂、乳油，为了提高有效组分利用率，在配制制剂时通常加入适量的表面活性剂。
本发明的技术方案还包括调节植物生长的方法：将本发明组合物按活性组分0.1-500ppm浓度施于需要调节生长的介质上，优选的使用浓度为1-100ppm。
对于某些应用，可根据需要在本发明的植物生长调节剂组合物中加一种或几种其他的杀菌剂、杀虫剂、植物生长调节剂或肥料等。由此可产生附加的优点和效果。
应明确的是，在本发明的权力要求所限定的范围内，可进行各种交换和变动。
具体实施方式
本发明的优点和积极效果：
与目前商品化的植物生长调节剂相比，本发明的邻氨基苯甲酰胺类化合物不仅具有更高的促进细胞分裂分化、促生根的效果，又具有杀菌效果，具有一药两用的优异功效。式I化合物促生根性能作用显著优于DA-6(胺鲜酯)、复硝酸钠、萘乙酸钠(见表3)。该类化合物还有良好的抑菌作用，对番茄早疫病菌、黄瓜灰霉病菌、小麦赤霉病菌、苹果轮纹病菌具有良好的防治效果(见表4)。葡萄田间试验结果表明，该类化合物对葡萄有一定的增产作用，而且提高葡萄的糖度(见表5)，改善葡萄口感和着色。由于该类化合物含有氨基，可制成水溶性盐，避免使用有机溶剂，是一种水溶性绿色环保型植物生长调节剂。本发明化合物及其盐还具有合成方法简便、环保、合成成本低、有效用量少等优点。因此，本发明化合物是一种性能优良的多功能植物生长调节剂，既防病害又增产，投入产出比高，具有很好的商品化及市场潜力。
具体实施方式
下列合成实例、制剂实例及生测实验结果可用来进一步说明本发明，但不意味着限制本发明。
合成实例
实例1、(1)式Ia化合物的制备
向250mL四口反应烧瓶中，加入0.1mol(16.3g)靛红酸酐和0.1mol(11.4g)2-氨基-5-甲基噻唑，加入150mL乙酸乙酯和5mL的乙酸，开启搅拌至均匀后，加热至回流，反应一段时间用薄层层析板检测原料消失后，降至室温，抽滤，用乙酸乙酯洗涤，烘干得到黄色固体，产率84.1％。熔点：196-199℃。
(2)式Ib化合物的制备
向250mL四口反应烧瓶中，加入0.1mol(16.3g)靛红酸酐和150mL乙酸乙酯，开启搅拌至均匀后，然后滴加0.15mol(15.3g)N,N-二甲基丙二胺，滴毕，缓慢升温至78℃反应，用薄层层析板检测原料消失后，降至室温，抽滤，用乙酸乙酯洗涤，烘干得到褐黄色固体，产率84.2％。熔点：70-75℃。
(3)式Ic化合物的制备
向250mL四口反应烧瓶中，加入0.1mol(16.3g)靛红酸酐和150mL乙酸乙酯，开启搅拌至均匀后，然后滴加0.15mol(14.55g)糠胺，滴毕，缓慢升温至回流，用薄层层析板检测原料消失后，降至室温，抽滤，用乙酸乙酯洗涤，烘干得到白色固体，产率80.2％。熔点：89.3-90.3℃。
合成的各化合物的1H NMR数据列于表1。
表1目标化合物的核磁数据
式Ⅰ化合物为难溶于水，因此可与等摩尔量的无机酸如盐酸、硫酸、硝酸或有机酸如柠檬酸、草酸等制成其铵盐，可配制成水剂。
也可将将式Ⅰ化合物加入10％的助剂APG和农乳601#做成5％的浓度的叶面肥药剂进行室内田间试验。
生物活性测试
实例2、黄瓜子叶扩张实验
实验方法：将挑选好的籽粒饱满的黄瓜种子用0.1％的氧化汞溶液表面消毒后，用蒸馏水浸泡8小时，放置于含有0.7％琼脂的培养皿中发芽，在26℃的恒温培养箱中培养72小时，待长出子叶后，取相同规格的子叶备用。选取子叶完全形成，大小一致的幼苗10片，均匀摆放在铺有2张定性滤纸的培养皿中，子叶完全正面朝下。取待测药液9mL，依次加入到已经编号的培养皿中。光照下，温度为26℃(300Lux)培养3天，测量子叶的总重量，然后与空白做对照，计算出相对活性R。
相对活性
式中，R表示生长促进率或抑制率，单位为百分率(％)；X1表示处理黄瓜子叶面积或鲜重，单位为平方毫米或毫克(mm2或mg)；X0表示对照黄瓜子叶面积或鲜重，单位为平方毫米或毫克(mm2或mg)。
被测试的化合物用DMF溶解，加0.1％的吐温-80和蒸馏水配制浓度分别为1mg/L、5mg/L、10mg/L、20mg/L。分别做3次处理，空白对照为清水处理的培养皿。
表2式Ⅰ化合物对黄瓜子叶扩张影响
由表2可知，在合适浓度下，式Ⅰ化合物对黄瓜子叶生长有促进作用。
实例3、黄瓜子叶生根测定
选用黄瓜种子津研4号，浸种2h后播于0.7％的琼脂上，25℃暗室培养72h，摘取子叶备用，取10片子叶放在直径6cm的培养皿中，内有一张滤纸片和30mL待测试液，25℃暗室培养5天，测叶柄茎部生根，第6天测根长和根鲜重。对合成的本发明的化合物(式I)进行测试，以购得的DA-6、复硝酚钠、萘乙酸钠为对比药剂，实验结果列于表3。
表3式Ⅰ化合物对黄瓜子叶生根的影响
从表3测定结果看出，本发明式I化合物对黄瓜子叶生根具有极显著的促进作用，在10ppm时生根促进率达95％以上。本发明化合物不仅促生根作用强，且使用安全，而对比植物生长调节剂则出现抑制作用或药害。
实例4、杀菌活性测试
根据《农药室内生物测定实验准则杀菌剂》，使用平皿法测定杀菌剂抑制病原真菌菌丝，如番茄早疫病菌(Alternaria solani)、黄瓜灰霉病菌(Botrytis cinerea)、小麦赤霉病菌(Gibberella zeae)、苹果轮纹病菌(Physalospora piricola)四种菌丝在平板表面上的生长抑制作用。首先，将供试药剂、对照试剂在无菌条件下稀释成一定的倍数，从低浓度到高浓度依次吸取1mL药液，注入预先融化了灭菌培养基的无菌锥形瓶中，充分摇匀，然后等量倒入3个直径为9cm的培养皿中，制成浓度为50μg/L的含药平板，并用无药剂的做相同处理作为空白对照，每处理不进行3个重复。将以上培养好的病原菌，在无菌条件下用直径5mm的灭菌打孔器，自菌落边缘切取菌饼，用接种器接种于含药平板中央，菌丝面朝上，盖上培养皿盖，每个培养皿一个，重复3次，在恒温28℃条件下培养48h，然后以十字交叉法测量菌落直径，并计算48h菌丝生长速率，然后计算防效。
药液的稀释倍数分别为1mg/L、10mg/L、100mg/L。
式I化合物对番茄早疫病菌、黄瓜灰霉病菌、小麦赤霉病菌、苹果轮纹病菌的生物活性数据，测试结果列于表4。
表4式Ⅰ化合物杀菌活性结果
由表4可知，式I化合物随着浓度的升高，对番茄早疫病菌、黄瓜灰霉病菌、小麦赤霉病菌、苹果轮纹病菌的杀菌活性逐渐提高，尤其是Ia在浓度为100mg/L时对番茄早疫病菌、黄瓜灰霉病菌、小麦赤霉病菌、苹果轮纹病菌抑菌率达90％以上。Ib在浓度为100mg/L时对番茄早疫病菌、小麦赤霉病菌抑菌率达90％以上，对黄瓜灰霉病菌、苹果轮纹病菌抑菌率达85％以上。Ic在浓度为100mg/L时对黄瓜灰霉病菌、小麦赤霉病菌、苹果轮纹病菌抑菌率达85％以上。
通过室内生物活性试验可知，本发明化合物既可以有促进细胞分裂的功效，又具有杀菌效果，达到了一药两用的目的。
实例5、葡萄田间试验
在葡萄的生长期内，利用本发明化合物一药两用的功效，进行田间试验。通过室内活性测试可以确定出化合物的使用浓度分别是：化合物Ia、Ic的在萌芽展叶期、开花坐果期可以稀释500倍，幼果膨大期稀释1000倍；化合物Ib的浓度在萌芽展叶期、开花坐果期稀释500倍，幼果膨大期稀释2000倍进行喷洒，清水做空白对照。在果实成熟期测量葡萄的糖度，计算葡萄的产量。结果列于表5。
表5式I化合物对葡萄产量及糖度的影响
从表5可知，式I化合物对葡萄有增产作用，增加糖度和口感，药剂处理的葡萄的成熟度高。而且在葡萄生长过程中发现，病害的发生率也少，证明有一药两用的功效。
Claims (4)
1.一种邻氨基苯甲酰胺类化合物，结构如通式I所示：
式中R为：
2.按照权利要求1所述的一种邻氨基苯甲酰胺类化合物的用途，其特征在于该化合物用作植物生长调节剂或杀菌剂。
3.一种植物生长调节剂组合物，含有权利要求1所述的通式I化合物作为植物生长调节剂活性组分和农业上或林业上可接受的载体。
4.一种杀菌剂组合物，含有权利要求1所述的通式I化合物作为杀菌剂活性组分和农业上或林业上可接受的载体。
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| CN106831494A (zh) * | 2017-03-14 | 2017-06-13 | 青岛科技大学 | 一种邻酰胺基二苯脲类化合物及其用途 |
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| 董淑祥: "钯催化N-取代苯胺邻位C-H键选择活性羰基化合物成邻氨基苯甲酰胺", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
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