CN106866505A - 乙酰水杨酸酯类植物生长调节剂 - Google Patents
乙酰水杨酸酯类植物生长调节剂 Download PDFInfo
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- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 16
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical class CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 title claims description 8
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- 101001031591 Mus musculus Heart- and neural crest derivatives-expressed protein 2 Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 229940068372 acetyl salicylate Drugs 0.000 description 1
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- 150000008064 anhydrides Chemical class 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种结构如式I所示的乙酰水杨酸酯类化合物，用作植物生长调节剂。式I化合物促进植物生根发芽，促进生长发育，有抗旱防病作用，有明显增产效果，生产使用成本低及使用安全，可用于农作物及果蔬的增产提质。其中R为
Description
技术领域 本发明属于农药中植物生长调节剂领域，具体涉及乙酰水杨酸酯类植物生长调节剂及其用途。
背景技术 植物生长调节剂作为农药中的一大类别，在农业增产增收、提高品质等方面发挥了重要的作用，在保障粮食安全、食品安全等方面越来越受到关注。水杨酸化学名为邻羟基苯甲酸，是植物体内普遍存在的内源信号分子之一，是一种植物激素，对植物具有重要的生理功能，水杨酸不仅可以调节植物的某些生长发育过程，还能够诱导植物产生抗病、抗低温、抗旱、抗盐和抗紫外线等抗逆性，抵抗不良因素造成的伤害。水杨酸在农业上常用于保鲜花卉、延缓果实成熟、提高好果率。在现有技术中，如本发明所述的乙酰水杨酸酯类(式I化合物)及其作为植物生长调节剂的用途在国内外未见公开。
发明内容 本发明的目的是提供一种乙酰水杨酸酯类植物生长调节剂，促进植物生根发芽，有抗旱防病作用，有明显增产效果，生产使用成本低及使用安全，可用于农作物及果蔬的增产提质。
本发明的技术方案如下：
一种乙酰水杨酸酯类植物生长调节剂，结构如式I所示：
式I化合物可由下列反应制得：
式中R定义同前。
具体制备方法见本说明书合成实例。
表1列出了部分通式I化合物的结构和物理性质。
表1部分通式I化合物的结构和物理性质
| 化合物 | 外观 | 熔点(℃) |
| 1 | 浅黄色油状液体 | -- |
| 1的柠檬酸盐 | 白色固体 | >300 |
| 2 | 浅黄色固体 | 137.5～162.4 |
本发明式I化合物作为植物生长调节剂的应用：化合物1水溶性小，将其制备成酸式盐如盐酸盐、柠檬酸、乳酸盐、草酸盐时，有良好的水溶性，可制备成水剂；化合物2水溶性小，应用时须加工成乳剂、悬浮剂、可湿性粉剂等，制剂中有效物含量为1～80％。使用时可以根据实际需要将上述制剂兑水稀释成0.1～1000μg/mL浓度的悬浮液或水乳液，进行浸根、蘸根、浸种、拌种、种子包衣或喷施茎叶。
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，该组合物中活性组分指式I化合物或式I化合物与其他活性组分如萘乙酸钠、复硝酚钠、吲哚丁酸钠等植物生长调节剂的一种、二种或多种组成的组合物，该植物生长调节剂组合物中还包括农业或林业上可接受的载体。
本发明的优点和积极效果：室内及田间药效试验表明，式I化合物对作物具有显著的促发芽、促生根、促生长、抗旱、抗病、增产提质作用。如在内蒙古干旱高温气候条件下，式I化合物100μg/mL浓度下在玉米生长的7叶期和抽雄前3～5天各喷洒一次，与未施用组对照，表现为茎杆粗壮、叶片宽厚、叶色浓绿，未出现茎叶干枯，增产达18-20％。式I化合物100μg/mL浓度下在小麦分蘖和出穗期各喷洒一次，增产达20-22％。式I化合物100μg/mL浓度下分三次处理分别在水稻返青期、拔节期和抽穗期各喷施一次，促进水稻生长发育，分蘖多，返青快，结实率高，抗稻瘟病能力强，提高水稻产量近10％。本发明式I化合物制备简单，生产及使用成本低，用量小，使用浓度范围宽，使用安全方便，既防病、抗逆又增产，是目前不可多得的多功能植物生长调节剂，具有商品化开发价值。
应该明确的是，在本发明的权利要求所限定的范围内，可进行各种变换和改动。
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、化合物1的合成
(1)乙酰水杨酰氯的合成
向250mL三口烧瓶中加入依次加入18.0g(0.1mol)乙酰水杨酸、150mL甲苯、14.3g(0.12mol)氯化亚砜，室温搅拌下滴加0.2mL N,N-二甲基甲酰胺，升温回流2h。TLC监测反应完成，旋蒸出溶剂和过量的氯化亚砜，得19.09g浅黄色油状液体，收率为96.2％。
(2)乙酰水杨酸-(2-吡啶-2-基)乙酯盐酸盐的合成
向250mL三口烧瓶中依次加入12.3g(0.1mol)2-吡啶乙醇，150mL乙酸乙酯，冰盐浴条件下搅拌滴加上述制得的23.8g(0.12mol)乙酰水杨酰氯与50mL乙酸乙酯组成的溶液。滴加完毕，室温搅拌反应2h；抽滤，滤饼用适量乙酸乙酯洗涤，干燥得白色固体30.3g，收率94.3％。
(3)乙酰水杨酸-(2-吡啶-2-基)乙酯(化合物1)的合成
向250mL反应瓶中加入上述制得的乙酰水杨酸-(2-吡啶-2-基)乙酯盐酸盐32.2g(0.1mol)、150mL水，搅拌溶解，加入100mL二氯甲烷，室温搅拌下滴加由15.9g(0.15mol)碳酸钠和80mL水配成的溶液，滴毕，继续搅拌0.5h，静置分层，分出下层有机相，用水洗涤两次(30mL×2)，有机相用无水硫酸钠干燥，旋蒸出溶剂二氯甲烷，得到浅黄色油状液体27.1g，收率95.1％。
化合物1的1H NMR(500MHz，DMSO-d6)，δ(ppm)：2.218-2.241(s，3H，CH3)，3.153-3.179(t，2H，CH2)，4.605-4.632(t，2H，CH2)，7.205-7.235(m，2H，Ar-H)，7.337-7.380(m，2H，Pyridyl-H)，7.649(t，1H，Ar-H)，7.713-7.716(t，1H，Pyridyl-H)，7.825-7.843(d，1H，Ar-H)，8.517-8.525(s，1H，Pyridyl-H)。
实例2、化合物1的柠檬酸盐的制备
向250mL反应瓶中依次加入9.6g(0.05mol)柠檬酸和80mL乙醇，搅拌溶解，搅拌下缓慢滴加14.25g(0.05mol)乙酰水杨酸吡啶乙基酯与20mL乙醇的混合液，滴毕，继续搅拌0.5h，旋蒸出溶剂，干燥得白色固体23.6g，收率99.1％。
同理可制得化合物1的乳酸盐、草酸盐。
实例3、化合物2的合成
(1)N-羟乙基萘二甲酰亚胺(式II化合物)的制备
在250mL三口烧瓶中分别加入19.8g(0.1mol)萘二甲酸酐和6.1g(0.1mol)乙醇胺，6.0g(0.1mol)醋酸，100mL水作溶剂，加热回流，反应完全后，冷却抽滤的淡黄色晶状固体，烘干，得23.4g，产率97.1％。
(3)化合物2的制备
在250mL三口烧瓶中分别加入24.1g(0.1mol)式II化合物和100mL甲苯，滴加20.5g(0.1mol)乙酰水杨酰氯与30mL甲苯组成的溶液，滴毕，加热回流下搅拌反应3.5h，TCL检测反应完全后，抽滤得浅黄色固体(式I化合物)32.6g，产率81.0％，熔点137.5℃～162.4℃。
化合物2的1H NMR(500MHz，DMSO-d6)，δ(ppm)：1.825(s，3H，CH3)，3.877-3.906(q，1H，CH2)，3.977-4.040(m，2H，CH2)，4.306-4.341(m，1H，CH2)，6.150-6.179(t，1H，Ar-H)，6.700-6.712(d，1H，Ar-H)，6.773-6.803(q，1H，Ar-H)，7.004-7.020(t，1H，Ar-H)，7.828-7.858(t，2H，Ar-H)，8.312-8.326(d，2H，Ar-H)，8.436-8.453(d，2H，Ar-H)。
生物活性测定
实例4、种子发芽实验
采用纸床发芽法进行。分别将式1化合物柠檬酸盐配制成5％的水剂，将30％化合物2悬浮剂和DA-6(河南郑氏化工有限公司出品)稀释成5％的化合物2悬浮剂和5％DA-6水剂，分别用蒸馏水稀释成浓度为10μg/mL、20μg/mL、30μg/mL、60μg/mL和120μg/mL的植物生长调节剂溶液。挑选子粒大小均匀、饱满的小麦种子，用次氯酸溶液对种子进行杀菌后，于烧杯中用上述稀释液浸种培养8h，每处理100粒种子，3次重复，处理后将种子均匀放置在有双层滤纸的培养皿中，种子之间保持一定的距离，摆放好种子之后将其放入全智能气候箱中25℃保温催芽处理，期间要定时加入蒸馏水使滤纸保持湿润，催芽期间观察各处理的发芽情况，胚芽长度约以种子长的1/2为标准，于24h后统计各培养皿中小麦种子发芽率，以相同浓度的DA-6和清水(CK)作对照，同时计算各稀释液发芽促进率，结果如下表2所示。
表2小麦种子发芽实验数据
由表2试验数据可见，本发明式I化合物各处理的发芽率均优于对比药剂DA-6，更显著优于清水处理(CK)。
实例5、浸种促生根实验
分别将式1化合物柠檬酸盐配制成5％的水剂，将30％化合物2悬浮剂和DA-6(河南郑氏化工有限公司出品)稀释成5％的化合物2悬浮剂和5％DA-6水剂，分别用蒸馏水稀释成浓度为10μg/mL、20μg/mL、30μg/mL、60μg/mL和120μg/mL的植物生长调节剂溶液。挑选子粒大小均匀、饱满的小麦种子，用次氯酸溶液对种子进行杀菌后，于烧杯中用上述稀释液浸种培养8h，每处理20粒小麦，3次重复，处理后将种子均匀放置在湿润的纸床上，种子之间保持一定的距离，以保证种子充分吸收水分，置床时胚部向上并朝向同一侧，摆放好种子之后将其放入全智能气候箱中进行催芽处理24h，期间要定时加入蒸馏水使纸床保持湿润。待小麦主根露出2mm左右，将其种在已经凝固的固体培养基中，然后放入全智能气候箱中进行培养。40h后用卡尺测量主根、茎高，并作详细的记录。以相同浓度的DA-6和清水处理(CK)作对照，结果如下表3所示。
表3浸种促生根实验数据
由表3的结果可以看出，本发明化合物在30μg/mL浓度时对小麦浸种促生根效果达到最佳，优于DA-6。
实例6、内蒙古玉米田间试验
试验地点：内蒙古呼和浩特市托克托县永圣域乡。时间：2016年5-10月。对象：品种为五谷704，春玉米，旱田。试验方法：在同一地块划分三个区，每区1亩，化合物1柠檬酸盐、化合物2、空白对照各1亩。在玉米生长的7叶期和抽雄前3～5天，用肩背式喷雾器人工喷洒各一次，浓度100μg/mL，每亩每次用量为15公斤水，与未施用空白组作对照。结果：施用组外观表现为茎杆粗壮、叶片宽厚、叶色浓绿，未出现茎叶干枯，颗粒饱满。空白亩产420公斤，施用化合物1柠檬酸盐亩产500公斤，增产80公斤，增产率19％，施用化合物2亩产505公斤，增产85公斤，增产率20％。
实例7、小麦田间试验
试验地点：山东省青岛市平度崔家集镇张家坊村。时间：2016年3-6月。对象：春小麦。试验方法：在同一地块划分三个区，每区1亩，化合物1柠檬酸盐、化合物2、空白对照各1亩。在小麦分蘖和出穗期用肩背式喷雾器人工喷洒各一次，浓度100μg/mL，每亩每次用量为15公斤水，与未施用空白组作对照。结果列于表4。
表4小麦田间试验结果
| 亩产(kg) | 增产率(％) | |
| 化合物1柠檬酸盐 | 660 | 20.0 |
| 化合物2 | 670 | 21.8 |
| 空白(清水) | 550 | -- |
施用化合物1柠檬酸盐亩增产110公斤，增产率20％；化合物2亩增产120公斤，增产率21.8％。
实例8、水稻田间试验
试验地点：于黑龙江省双鸭山市饶河县。时间2016年5-11月。对象：水稻品种为龙粳40。试验方法：采用大区对比，每处理面积15亩，不设重复，以常规区为对照。式I化合物100μg/mL浓度下分三次处理分别在水稻返青期、拔节期和抽穗期各喷施一次。
(1)对水稻生长发育的影响：结果列于表5。通过结果来看，能够显著促进水稻生长发育，分蘖多，生育进程快。到后期植株形状明显好于常规。
表5对水稻生长发育的影响
(2)收获期室内考种及产量：结果列于表6。结果表明，水稻的稻瘟病的病粒率显著低，处理区水稻稻瘟病的病粒率为21％，对照区为38％，较对照区低16％。千粒重增加0.4-0.5g，亩产增加产量50-54公斤，增产率9-9.8％。
表6对水稻产量形状的影响
综上可见，本发明化合物对玉米、小麦、水稻有明显增产效果。
Claims (3)
1.一种乙酰水杨酸酯类植物生长调节剂，结构如式I所示：
其中R为
2.根据权利要求1所述的式I化合物的用途，其特征在于式I化合物用作植物生长调节剂。
3.一种植物生长调节剂组合物，含有权利要求1所述的式I化合物作为植物生长调节剂活性组分和农业或林业可接受的载体。
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