CN106749205B - 一种吡啶乙氧基香豆素类植物生长调节剂 - Google Patents
一种吡啶乙氧基香豆素类植物生长调节剂 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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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)
Abstract
本发明公开了一种结构如式I所示的吡啶乙氧基香豆素类化合物，用作植物生长调节剂。式I化合物具有优异的促发芽、生根及增产提质作用，可广泛用于农业或林业的增产或成活率提高。
Description
技术领域
本发明属于农药中植物生长调节剂领域，具体涉及一种吡啶乙氧基香豆素类植物生长调节剂。
背景技术
植物生长调节剂在控制种子萌芽和休眠，促进生根，促进细胞伸长及分裂，控制侧芽或分蘖，控制株型，控制开花，诱导无子果实，疏花疏果，控制落果，控制果形或成熟期，增强抗逆性(抗病、抗旱、抗盐分、抗冻)，增加营养成分，改进水果色泽和口感，增强吸收肥料能力等方面起到了积极的作用。
植物生长抑制剂抑制顶端分生组织生长，使植物丧失顶端优势，侧枝多，叶小，生殖器官也受影响。天然的植物生长抑制剂有脱落酸、肉桂酸、香豆素、水杨酸等。香豆素广泛分布于高等植物中，在伞形科、芸香科中较多，在虎耳草科、菊科、瑞香科、豆科中也存在。香豆素类化合物有植物生长调节活性，低浓度刺激植物发芽、生长；高浓度抑制植物发芽、生长。庞淑敏等人报道香豆素对马铃薯试管苗有诱导效应，30mg/L香豆素利于试管薯单粒质量的提高(庞淑敏，方贯娜，李建欣，赵建设，3种植物生长调节剂对马铃薯试管苗的诱导效应，长江蔬菜(学术版)，2009，20：25-27)。文献(朱述钧，王春梅，沈寿国，石志琦，香豆素类化合物在农业上的应用，江西农业学报，2006，18(2)：97-100)报道，香豆素除具有植物生长调节活性外，在植物中香豆素能够清除活性氧，减少紫外线照射氧化损伤，达到保护植物的作用。香豆素在体外有抑菌活性，同时在植物体内可以积累保护植物免受病原真菌的感染。如7-甲氧基-8-异戊烯基香豆素(又名蛇床子素)对辣椒疫霉病菌、番茄灰霉病菌、小麦赤霉病菌等病原真菌有显著的抑制作用，尤其对瓜类白粉病菌有特效。
在现有技术中，如本发明所述的一种吡啶乙氧基香豆素类植物生长调节剂及其活性未见公开。
发明内容
本发明的目的在于提供一种促进种子萌发、促生根、增产、使用成本低及使用安全的植物生长调节剂，具体的说是提供一种吡啶乙氧基香豆素类植物生长调节剂，它可用于农业、林业的大幅度增产或成活率提高。
本发明的技术方案如下：
本发明提供了一种吡啶乙氧基香豆素类植物生长调节剂，其结构如式I所示：
化合物I可由下列反应制得，具体制备方法见本发明合成实例。
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。本发明所述的植物生长调节剂组合物也可根据需要在本发明的植物生长调节剂组合物中，添加一种或几种其他的杀虫剂、杀菌剂、大量或微量元素肥料等，由此会产生附加的优良效果。
本发明的组合物的剂型可以是悬浮剂、乳剂、微乳剂、可湿性粉剂、水分散性粒剂等，为了提高有效组分的利用率，在配制制剂时通常加入适量的表面活性剂。
本发明的优点和积极效果：
本发明所述的式I化合物化学结构简单，含有香豆素基团和吡啶基团，不仅有植物生长调节活性，而且有抗菌活性，这点是目前多数高效植物生长调节剂所不具备的。式I化合物还具有杀菌活性，式I化合物对苹果轮纹病菌(Physalospora piricola)、小麦纹枯病菌(Rhizotonia cerealis)、小麦赤霉病菌(Fusarium graminearum)、黄瓜枯萎病菌(Fusarium oxysporum)、玉米小斑病菌(Helminthosporium maydis)、水稻纹枯病菌(Rhizoctonia solani)、西瓜炭疽病菌(Colletotrichum lagenarium)、辣椒疫霉病菌(Phytophthora capsici)均有一定的抑制作用(见实例5，表3)。不仅如此，本发明的植物生长调节剂同现有的植物生长调节剂相比具有优越的综合性能，用本发明的植物生长调节剂20μg/mL溶液浸泡小麦种子24h，可显著提高小麦发芽率，其发芽促进率达36.3％，大大高于DA-6(见实例3，表1)；在促生根方面明显优于DA-6(见实例4，表2)。大田试验表明，该植物生长调节剂可使小麦增产18-22％，使玉米茎杆粗壮、叶色浓绿且宽厚，延长叶片寿命，提高抗旱、抗涝、抗病能力，增产20-24％；用于大姜、土豆，茎块增大，用于辣椒、番茄等表现出茎秆粗壮、叶色浓绿，增产达20％以上。式I化合物不仅具有优良的植物生长调节活性，而且该化合物兼具有良好的杀真菌作用，其综合功效明显优于单一生长调节活性的植物生长调节剂。同时，香豆素和吡啶基团易生物降解，属于环境友好型产品。本发明植物生长调节剂具有成本低、使用安全方便、增产提质、防病害的优点，具有很高的应用价值和商品化潜力。
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、式I化合物的合成
(1)式II化合物的合成：
向250mL三口烧瓶中加入依次加入12.3g(0.1mol)2-吡啶乙醇、150mL乙酸乙酯，同时加入11.1g(0.1mol)三乙胺作缚酸剂，冰水浴搅拌下滴加13.7g(0.12mol)甲基磺酰氯，冰水浴反应5h。薄层色谱监测反应完成，水洗三次，分出有机层，用无水硫酸钠干燥，旋蒸得16.5g浅黄色油状液体，收率为82.0％。
(2)式I化合物的合成：
向250mL三口烧瓶中依次加入16.2g(0.1mol)四羟基香豆素，150mL甲苯，16.6g(0.12mol)碳酸钾粉末，滴加24.1g(0.12mol)式II化合物与甲苯的混合溶液，滴毕，升温回流搅拌反应4.5h。反应完毕，冷却到室温后，150mL水洗三次，分出有机层，用无水硫酸钠干燥，旋蒸得浅棕色油状液体，用甲醇纯化得浅黄色固体18.7g，收率70.2％。熔点：85.7-87.9℃。
式I化合物的1H NMR(500MHz，DMSO-d6)，δ(ppm)：3.296-3.342(q，2H，CH2)，4.588-4.613(t，2H，CH2)，5.952(s，1H，CH)，7.240-7.264(q，1H，Ar-H)，7.302-7.332(t，1H，Ar-H)，7.365-7.381(d，1H，Pyridyl-H)，7.441-7.460(d，1H，Pyridyl-H)7.613-7.649(t，2H，Ar-H)，7.734-7.767(m，1H，Ar-H)，8.522-8.530(d，1H，Pyridyl-H)。
制剂实施例
实例2、10％式I化合物悬浮剂的制备：
分别称取15g式I化合物，2g木质素磺酸钠，3g聚羧酸盐分散剂Sokalan CP 5(马来酸-丙烯酸钠盐)，1g有机硅乳消泡剂(THIX-108水性硅乳化消泡剂)，2g硅酸镁铝和5g乙二醇于250mL烧杯中，加入77g水，搅拌均匀，用砂磨机研磨2h，转速为3000转/分，检测粒度3-5μm，得白色流动性悬浮剂。
生测实施例
实例3、种子发芽实验
采用纸床发芽法进行。分别将式I化合物柠檬酸盐和DA-6配制成5％的水剂，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1所示。
表1小麦种子发芽实验数据
由表1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4、浸种促生根实验
分别将式I化合物柠檬酸盐和DA-6配制成5％的水剂，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2所示。
表2浸种促生根实验数据
由表2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。
杀菌活性测定
实例5、将一定量药剂溶解在适量N,N-二甲基甲酰胺(DMF)内，然后用含有一定量吐温20乳化剂水溶液稀释至50mg/L。采用离体平皿法，供试病原菌：黄瓜枯萎病菌(Fusarium oxysporum)、苹果轮纹病菌(Physalospora piricola)、小麦纹枯病菌(Rhizotonia cerealis)、玉米小斑病菌(Helminthosporium maydis)、西瓜炭疽病菌(Colletotrichum lagenarium)、小麦赤霉病菌(Fusarium graminearum)、辣椒疫霉病菌(Phytophthora capsici)、水稻纹枯病菌(Rhizoctonia solani)。采用菌体生长速率测定法，具体过程是：在无菌条件下各吸取1mL药液注入培养皿内，加入9mLPDA培养基(马铃薯葡萄糖琼脂培养基)，摇匀后制成100mg/L含药平板，以添加1mL灭菌水的平板做空白对照。用直径4mm的打孔器沿菌丝外缘切取菌盘，移至含药平板上，每次处理重复三次。将培养皿放在24±1℃恒温培养箱内培养，72h后调查各处菌盘扩展直径，求平均值，与空白对照比较计算相对抑菌率，测试浓度为100μg/mL，测试结果见如下表3。
防效(％)＝(空白菌落直径－处理菌落直径)/(空白菌落直径－4)×100％
表3杀菌试验防效(％)数据
由上表数据可见，式I化合物对苹果轮纹病菌(Physalospora piricola)、小麦纹枯病菌(Rhizotonia cerealis)、小麦赤霉病菌(Fusarium graminearum)、黄瓜枯萎病菌(Fusarium oxysporum)、玉米小斑病菌(Helminthosporium maydis)、水稻纹枯病菌(Rhizoctonia solani)、西瓜炭疽病菌(Colletotrichum lagenarium)、辣椒疫霉病菌(Phytophthora capsici)的均有一定的防效。
Claims (2)
1.一种吡啶乙氧基香豆素类植物生长调节剂，结构如式I所示：
2.一种植物生长调节剂组合物，含有权利要求1所述的式I化合物作为活性组分和农业上或林业上可接受的载体。
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| CN103524407A (zh) * | 2013-11-01 | 2014-01-22 | 青岛农业大学 | 一组2-氟-3-吡啶甲酰化合物 |
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| CN103524407A (zh) * | 2013-11-01 | 2014-01-22 | 青岛农业大学 | 一组2-氟-3-吡啶甲酰化合物 |
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