CN110642859B - 一种含嘧啶硫酮嘌呤类化合物及其用途 - Google Patents
一种含嘧啶硫酮嘌呤类化合物及其用途 Download PDFInfo
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
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Abstract
本发明公开了一种结构如式I所示的一种含嘧啶硫酮嘌呤类化合物及其作为植物生长调节剂的用途。
Description
技术领域 本发明属于农用杀虫、杀螨及杀菌剂领域，具体涉及一种含嘧啶硫酮嘌呤类化合物及其用途
背景技术 植物生长调节剂在促进种子发芽，促进生根、生长，促进细胞伸长及分裂，控制果形或成熟期，增强抗逆性(抗病、抗旱、抗盐分、抗冻)，增加营养成分等方面起到了积极的作用。嘌呤类化合物，如6-糠基氨基嘌呤(又名激动素)、玉米素、6-苄基氨基嘌呤(6-BA)等具有细胞分裂活性，可促进植物细胞生长，抑制植物叶绿素的降解，提高氨基酸的含量，延缓叶片衰老，诱导芽的分化，促进侧芽生长，促进细胞分裂，还能减少植物体内叶绿素的分解，具有延缓和抑制植物衰老、保绿作用。
在现有技术中，如本发明所述的一种含嘧啶硫酮嘌呤类化合物及其作为植物生长调节剂的用途未见公开。
发明内容
本发明的目的在于提供一种促进细胞分裂、促生根、增产、使用安全、兼有杀菌作用的植物生长调节剂，具体的说是提供一种含嘧啶硫酮嘌呤类植物生长调节剂，它可用于农作物和水果、蔬菜的大幅度增产和提质。
本发明的技术方案如下：
本发明提供了兼具杀菌作用的含嘧啶硫酮嘌呤类植物生长调节剂，结构式如Ⅰ所示：
式I化合物可由下列反应制得，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、6-BA、DA-6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化合物是一种含嘧啶硫酮嘌呤类化合物，是一种兼具杀菌活性的植物生长调节剂。黄瓜子叶扩张试验表明，本发明的植物生长调节剂具有优良的细胞分裂活性，其活性显著高于6-BA(见实例3，表1)。式I化合物具有促生根作用，在促生根方面明显优于6-BA(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20％左右，使玉米增产25％左右，使马铃薯增产22％左右。式I化合物或使作物茎杆粗壮、叶色浓绿且宽厚，提高抗旱、抗涝、抗病能力。用于番茄表现出果形正、果实大而重、坐果率提高、果实保鲜期长，增产达22％以上。式I化合物还具有杀菌活性，对苹果轮纹病菌(Physalosporapiricola)、水稻纹枯病菌(Rhizoctonia solani)、小麦赤霉病菌(Gibberella zeae)、马铃薯晚疫病菌(Phytophthora infestans)均有防治作用。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，该化合物易生物降解，属于环境友好型产品。本发明植物生长调节剂合成方法简单，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
下列合成实例及生测结果可用来进一步说明本发明，但并不意味着限制本发明。
合成实例
实例1、式Ⅰ化合物的制备：
(1)2-(6-氨基嘌呤基)-乙醇的制备：
在250mL三口烧瓶中加入80g二氯甲烷，加入13.61g(0.10mol)次黄嘌呤和2滴N,N-二甲基甲酰胺(DMF)，充分搅拌后缓慢滴加18.40g(0.12mol)溶于二氯甲烷的三氯氧磷溶液，滴加完毕后，以TLC法跟踪反应进程，搅拌回流(40℃)反应3h。反应结束后，将反应液转移至250mL单口烧瓶中，旋蒸除去溶剂和部分未反应的三氯氧磷。旋蒸产物加碳酸氢钠水溶液，搅拌，使用布氏漏斗进行抽滤，水洗，干燥，得黄色粉末状固体11.05g(0.072mol)，收率为71.5％。
在250mL三口烧瓶中加入100g乙醇溶剂，加入15.46g(0.1mol)6-氯嘌呤，充分搅拌，加入12.22g(0.2mol)乙醇胺，以TLC法跟踪反应进程，搅拌回流(78℃)反应2h，溶液会从黄色变为深绿色。反应完全后，冷却，抽滤，并用乙醇洗涤去过量的乙醇胺，烘干，得淡黄绿色固体11.59g(0.065mol)，收率64.7％。
(2)肉桂酰氯的合成：
在250mL三口烧瓶中，加入80g二氯甲烷溶剂，称取14.82g(0.1mol)肉桂酸溶于二氯甲烷溶剂中，滴入两滴N,N-二甲基甲酰胺(DMF)作为催化剂，充分搅拌后滴加14.28g(0.12mol)氯化亚砜，滴加完毕后，搅拌回流(40℃)反应3h，此时溶液变得澄清透明，以TLC法跟踪反应进程。反应完全后，将反应液转移至250mL单口烧瓶中，旋蒸除去溶剂和未反应的氯化亚砜，得到黄色油状液体15.58g(0.094mol)，收率93.52％.
(3)中间体2-(6,9-二氢-5H-嘌呤-6-氨基)-肉桂酸乙酯的合成：
在250mL三口烧瓶中，加入70g二氯甲烷溶剂，加入14.33g(0.08mol)2-(6-氨基嘌呤基)-乙醇和8.10g(0.08mol)三乙胺，溶解在二氯甲烷溶剂中。将15.58g(0.094mol)肉桂酰氯溶于20g二氯甲烷中，在冰水浴下，用恒压滴液漏斗滴加到三口烧瓶中，滴加完毕后，搅拌回流(40℃)反应2h，以TLC法跟踪反应进程。反应结束后，抽滤，收集滤饼。在400mL的烧杯中，加入15g碳酸氢钠和200mL水，搅拌，配成饱和碳酸氢钠水溶液。将干燥的滤饼，倒入盛有饱和碳酸氢钠水溶液的烧杯中，用玻璃棒搅拌3min，将多余的肉桂酰氯转化为盐溶于水中。抽滤，用水洗涤三次，滤饼置于烘箱中干燥。干燥后得到黄绿色粉末状固体16.89g(0.055mol)，收率68.27％。
(4)式Ⅰ化合物的制备：
在250mL三口烧瓶中，加入80g DMF溶剂，称取6.19g(0.02mol)2-(6,9-二氢-5H-嘌呤-6-氨基)-肉桂酸乙酯和2.28g(0.03mol)硫脲，溶于DMF溶剂中，加入4.3g(0.025mol)对甲苯磺酸做催化剂。在80℃下搅拌加热2h，再升温至100℃搅拌加热5h。反应结束后，冷却，向三口烧瓶中加水，有大量固体物质生成，直至无明显固体生成时，停止加水，静置20min。用布氏漏斗进行抽滤，滤饼再用水洗涤三次，收集滤饼，将滤饼干燥，得到2.92g(0.0079mol)黄白色粉末状固体，收率39.73％。可采用柱色谱对样品进行纯化。式Ⅰ化合物的熔点：225.0～226.2℃。式I化合物的1H NMR(500MHz，DMSO-d6)，δ(ppm)：8.20(s,1H),8.11(s,2H),7.68(t,J＝4.8Hz,3H),7.62(d,J＝16.1Hz,2H),7.42(dd,J＝4.9,1.9Hz,5H),4.36(t,J＝5.7Hz,4H),3.82(s,1H).。
制剂实施例
实例2、10％式I化合物悬浮剂的制备：
分别称取10g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。
生物活性测定
实例3、黄瓜子叶扩张试验
供试黄瓜品种为津研4号，浸种后播种在盛有0.7％琼脂的带盖搪瓷盘中，置于26℃暗环境下培养72h，精选大小均匀一致的子叶待用，样品制备采用植物激素活性物质测定中的滤纸片法。
具体做法是：将10％式I化合物悬浮剂用蒸馏水稀释成浓度100mg/L、10mg/L溶液。分别取各母液0.3mL均匀滴于Φ6cm的滤纸片上，待溶剂风干后，在Φ6cm的培养皿中，各放入含样品的滤纸片1张，加入蒸馏水3mL，子叶10片，即为100及10mg/L处理。以蒸馏水为对照，置于26℃，3000Lux光强环境下培养，72h后测量每10片子叶鲜重。以6-苄氨基嘌呤(6-BA)做对照。每处理2次重复，结果取平均值，试验结果见表1。
表1黄瓜子叶扩张对比试验
实例4、浸种促生根实验
分别将式I化合物10％悬浮剂、6-BA稀释成5％的式I化合物悬浮剂、5％6-BA悬浮剂，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。同时以相同浓度的6-BA和清水处理(CK)作对照，结果如下表2所示。
表2小麦种子促生根实验
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，明显优于对照6-BA。
杀菌活性测试
实例5、根据《农药室内生物测定实验准则杀菌剂》，采用平皿法测定通式I化合物的杀菌效果。采用离体平皿法，供试病原菌：苹果轮纹病菌(Physalospora piricola)、水稻纹枯病菌(Rhizoctonia solani)、小麦赤霉病菌(Gibberella zeae)、马铃薯晚疫病菌(Phytophthora infestans)。采用菌体生长速率测定法，具体过程是：用等量的二甲基亚砜(DMSO)将式I化合物溶解，分别用现配的0.1％的吐温-80水溶液稀释成50μg/L，空白为DMSO和0.1％的吐温-80水溶液，DMSO不超过总量的2％。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杀菌抑制率(％)数据
由表3可见，本发明化合物表现出了一定的杀菌活性。
Claims (3)
1.一种植物生长调节剂，其结构如式I所示的一种含嘧啶硫酮嘌呤类化合物，
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。
3.权利要求1所述式I化合物控制农作物菌害的用途。
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