CN106800549A - 一种咪唑酸萘二甲酰亚胺基乙酯类化合物及其用途 - Google Patents
一种咪唑酸萘二甲酰亚胺基乙酯类化合物及其用途 Download PDFInfo
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Abstract
本发明公开了一种结构如式I所示的一种咪唑酸萘二甲酰亚胺基乙酯类化合物,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,且有一定的杀菌作用,可广泛用于农业或林业的增产、防病害及成活率提高。
Description
技术领域本发明属于农药中植物生长调节剂领域,具体涉及一种咪唑酸萘二甲酰亚胺基乙酯类化合物及其作为植物生长调节剂的用途。
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***,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。
一些咪唑类化合物具有杀真菌作用,如用于农林业真菌防治的抑霉唑(结构式1)、咪鲜胺(结构式2)。咪鲜胺为高效、广谱、低毒型杀菌剂,具有内吸传导、预防保护治疗等多重作用,主要用于防治子囊菌和半知菌引起的多种农作物病害,常用作种子处理剂和水果防腐保鲜剂,常规使用防治柑橘、香蕉、苹果、茄子、甜瓜、番茄等瓜果蔬菜的炭疽病、叶斑病、蒂腐病、青霉病、绿霉病等,还可防治水稻恶苗病、稻瘟病及小麦赤霉病等。
专利(US2547542A,19510403)公开了一种结构如下3式所示的乙酸萘二甲酰亚胺基乙酯类化合物,可用作植物生长调节剂;专利(CN103641781A,20140319)公开了一种结构如下4式所示的萘二甲酰亚胺取代的N,N-二甲基丙胺及其盐,用作植物生长调节剂;专利(CN103724265A,20140416)公开了一种结构如下5式所示的萘二甲酰亚胺取代的甜菜碱型植物生长调节剂。
在现有技术中,如本发明所述的一种咪唑酸萘二甲酰亚胺基乙酯类化合物及其植物生长调节活性和杀菌活性在国内外未见公开。
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咪唑酸萘二甲酰亚胺基乙酯类植物生长调节剂,它可用于农作物和水果、蔬菜的大幅度增产、提质、杀菌、保鲜。
本发明的技术方案如下:
本发明提供了一种兼有杀菌作用的咪唑酸萘二甲酰亚胺基乙酯类植物生长调节剂,其结构如式I所示:
式I化合物可由下列反应制得:
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、DA-6、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化合物是一种结构新颖的植物生长调节剂,在分子中由于咪唑酸酯基团的存在,使该化合物不仅保留了萘二甲酰亚胺类化合物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。式I化合物具有促进种子萌发、促生根作用,在促生根方面优于DA-6。大田试验表明,该植物生长调节剂可使小麦增产达18~22%,可使玉米茎杆粗壮、叶色浓绿、增产达25~30%;提高苹果中可溶性糖和VC含量,使口感更甘甜,提高一级果率。式I化合物对苹果轮纹病菌(Physalospora piricola)、小麦赤霉病菌(Fusarium graminearum)的防效较高,对黄瓜枯萎病菌(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)、小麦纹枯病菌(Rhizotonia cerealis)有一定防效。本发明植物生长调节剂具有成本低、多功能、使用安全方便的优点,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化合物的制备
(1)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,冷却抽滤得淡黄色晶状固体,烘干,得23.4g固体,产率97.1%。
(2)式III化合物的制备
在250mL三口烧瓶中分别加入24.1g(0.1mol)式II化合物和100mL乙酸乙酯,同时加入11.1g(0.11mol)三乙胺作缚酸剂,滴加11.5g(0.1mol)甲基磺酰氯与30mL乙酸乙酯组成的溶液,冰水浴条件下反应,滴毕,冰水浴下搅拌反应3.5h。反应完后加水溶解三乙胺盐酸盐,抽滤得白色固体(式III化合物)28.4g,产率89.0%。
(3)式I化合物的制备
在250mL三口烧瓶中分别加入31.9g(0.1mol)式III化合物和100mL二氯甲烷,滴加17.8g(0.11mol)N,N′-羰基二咪唑(CDI)与30mL二氯甲烷组成的溶液,冰水浴条件下反应,滴毕,冰水浴下搅拌反应3h。反应完后抽滤得白色固体(式I化合物)27.8g,产率83.0%,熔点200.8℃~209.5℃。
式I化合物的氢核磁数据如下:
1HNMR(500MHz,DMSO-d6),δ(ppm):4.480-4.490(t,2H,CH2),4.642-4.662(t,2H,CH2),7.456-7.488(t,2H,Imidazole-H),7.855-7.886(t,2H,Ar-H),8.124(s,1H,Imidazole-H),8.456-8.500(q,4H,Ar-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。
生物活性测定
实例3、种子发芽实验
采用纸床发芽法进行。分别将30%式I化合物悬浮剂和DA-6水剂(河南郑氏化工有限公司出品)稀释成5%的式I化合物悬浮剂和5%DA-6水剂,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,同时以相同浓度的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
由表1实验数据可见,本发明式I化合物处理的小麦发芽率整体上优于对比药剂DA-6,更显著优于清水处理(CK)的情况。
实例4、浸种促生根实验
分别将30%式I化合物悬浮剂和DA-6水剂(河南郑氏化工有限公司出品)稀释成5%的式I化合物悬浮剂和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。同时以相同浓度的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,明显优于对照药剂DA-6。
实例5、田间实验:对苹果实验共设3个处理,每个处理选择新嘎拉苹果树上3个生长势相当的大枝进行,试验随机取株,单株小区,3次重复,分别在红富士苹果幼果期和果实膨大期各喷施一次,叶面喷施清水作为对照,收获后,分别测量苹果的品质指标,其中,VC含量采用2,6-二氯酚靛酚法测定,可溶性糖含量采用蒽酮比色法测定,结果如下表3。
表3苹果品质指标试验数据
在对苹果进行叶面喷施后,在提高苹果的产量同时,其外观和内在品质均显著改善,如提高了苹果中VC、可溶性糖含量,可以看出本发明式I化合物是一种优良的植物生长调节剂。
杀菌活性测定
实例6、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1000mg/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4。
防效(%)=(空白菌落直径-处理菌落直径)/(空白菌落直径-4)×100%
表4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)、小麦赤霉病菌(Fusarium graminearum)的防效较高,对黄瓜枯萎病菌(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)、小麦纹枯病菌(Rhizotonia cerealis)有一定防效。
Claims (3)
1.一种咪唑酸萘二甲酰亚胺基乙酯类化合物,其结构如式I所示,
2.按照权利要求1式I化合物作为植物生长调节剂的用途。
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化合物作为活性组分和农业上或林业上可接受的载体。
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