CN101772479B - 利用二环丙烯化合物抑制植物中乙烯响应的方法 - Google Patents
利用二环丙烯化合物抑制植物中乙烯响应的方法 Download PDFInfo
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- A—HUMAN NECESSITIES
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- A01N3/00—Preservation of plants or parts thereof, e.g. inhibiting evaporation, improvement of the appearance of leaves or protection against physical influences such as UV radiation using chemical compositions; Grafting wax
- A01N3/02—Keeping cut flowers fresh chemically
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- A—HUMAN NECESSITIES
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- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
- A23B7/14—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10
- A23B7/144—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of gases, e.g. fumigation; Compositions or apparatus therefor
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B7/00—Preservation or chemical ripening of fruit or vegetables
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- A23B7/153—Preserving or ripening with chemicals not covered by groups A23B7/08 or A23B7/10 in the form of liquids or solids
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Abstract
公开了应用二环丙烯化合物及其组合物来阻断植物中乙烯受体的方法。方法包括将有效的乙烯响应-抑制量的二环丙烯化合物或其组合物应用于植物。还提供了二环丙烯化合物或者其对映体、立体异构体或盐。
Description
相关申请数据
本申请要求于2007年6月22日提交的美国临时申请序列号60/945,782和于2007年7月19日提交的美国临时申请序列号60/950,645的优先权。在此将各申请所公开的内容全部引入作为参考。
政府支持的声明
这项研究的方面得到了两国间农业研究与发展基金(BARD)依据授权号US-IS-3493-02CR的支持。美国政府拥有这项发明一定的权利。
发明的技术领域
本发明主要涉及通过将二环丙烯化合物及其组合物应用于植物来阻断植物和植物材料中乙烯响应的方法。本发明进一步涉及二环丙烯化合物,其对映体、立体异构体和盐。
发明的背景技术
已知乙烯调节植物中的各种生长现象。通常参见Fritz等人的美国专利No.3,879,188。认为该机能通过在植物中的特定的乙烯受体来实现。除了乙烯以外,许多化合物与该受体相互作用:一些仿效乙烯的作用;而另一些防止乙烯结合,从而抵消其作用。
许多阻断乙烯作用的化合物通过结合至乙烯的结合位点来阻断乙烯的作用。令人遗憾的是,它们往往在几个小时内从结合位点扩散开。参见E.Sisler和C.Wood,Plant Growth Reg.7,181-191(1988)。这些阻断性化合物可以用来抵消乙烯的作用。然而,这些化合物的问题是,如果要达到持续超过几个小时的效果,暴露必须是连续的。
光亲合性标记已用于生物研究,以永久性方式-通常通过生成卡宾或氮宾中间体来标记结合位点。这些中间体普遍是反应性的,并且和许多成分迅速无差别地反应。然而,已经结合的化合物大部分都是和结合位点反应。初步研究结果表明,环戊二烯是一种有效的阻止乙烯结合的阻断剂。参见E.Sisler等人,Plant Growth Reg.9,157-164(1990)。Sisler等人的美国专利No.5,100,462描述了重氮环戊二烯及其衍生物抵制植物中乙烯响应的方法。Sisler等人的美国专利No.5,518,988描述了具有C1到C4烷基的环丙烯在阻断乙烯作用中的用途。
尽管有这些努力,但是,在本领域中依然需要在农业生产和/或园艺产品中提供改进的植物成熟和老化控制以及抵制乙烯-诱导过程的那些的其他方法。
发明简述
本发明包括如式I的二环丙烯化合物,其对映体、立体异构体或盐:
其中:
m和n独立地为从0到4的整数;
R1和R2独立地为C1-C20烷基、C2-C20烯基或C2-C20炔基,其中R1或R2中的至少一个是C1-C5烷基、C2-C5烯基或C2-C5炔基;和
L选自由共价键、磷、氧、硫、C1-C20烷基、C2-C20烯基、C2-C20炔基、C3-C8环烷基、杂环基和芳基组成的组。
在一些实施方案中,该化合物具有以下结构:
在特别的实施方案中,该化合物具有以下结构:
本发明的实施方案进一步提供组合物,其包括:(a)至少一种式I的化合物;和(b)辅助剂,例如农业上可接受的载体。
本发明进一步包括在植物和植物材料中抑制乙烯响应的方法。方法包括抑制植物中的乙烯响应,包括向植物应用有效的乙烯响应-抑制量的式I化合物或者组合物,该组合物包括至少一种式I化合物;和(b)辅助剂。在一些实施方案中,该化合物包括具有以下结构的那些:
应用这些化合物于植物可以通过以下方式进行:使植物接触气态或盐形式的化合物或其混合物,使植物接触包含该化合物的固体,应用包含该化合物的喷雾(spray),在包含该化合物的组合物中浸渍植物,以及将该化合物加入到含有植物的容器中。此外,本发明的化合物可以应用于开放或封闭的系统。在特别的实施方案中,本发明的化合物可用于户外例如大田作物或园林植物。
本发明的实施方案进一步提供延长切花或新鲜农产品的寿命的方法,包括将有效的寿命延长量的本文所述二环丙烯化合物应用于切花或新鲜农产品。
本发明的方面可能会导致延长农产品如水果和蔬菜的耐贮性和货架期,延长切花的贮存和瓶插寿命,延长大田作物的收获时间和/或延长园林植物的寿命。
根据本发明进一步方面,本文所描述的化合物有助于使维管植物免于乙烯调节过程。
附图简要说明
图1.1,6-二环丙烯基-己烷对黄化豌豆植物生长的影响。
发明详述
乙烯受体被认为形成由受体二聚体亚单元组成的高阶群。受体二聚体可以通过直接接触来影响邻近的二聚体的信号状态。因此,来自许多受体的传导物质可以由单一的配体结合过程而改变。二环丙烯化合物可以参与乙烯受体群中的交联。本文所披露的化合物可以表现出显著的抗乙烯活性。在一些实施方案中,这些化合物是挥发性的,在不同温度下有效工作,当被用作气体时在0.3nLL-1下是活性的和/或保护水果免受乙烯长达约42天。
除非另有规定,文中所用技术和科学用语具有如本发明所属技术领域技术人员通常理解相同的含义。此外,文中引用的所有出版物、美国专利申请、美国专利和其他参考资料以其全部内容纳入作为参考。
根据本领域技术人员的普通技术知识,并根据阐明于美国专利No.6,365,549、美国专利No.6,194,350和美国专利No.5,518,988中的信息,在本文中描述的公开内容的基础上,本发明可以被实施。所有这些公开内容均全部纳入作为参考。
可用于实现本发明的二环丙烯化合物可以通过本领域技术人员已知的各种方法制备。例如,如Baird等人在Preparation and Lithiation of 1-Halogenocyclopropenes,J.CHEM.SOC.PERKIN TRANS.I 1845-53(1986)中所述。此外,二环丙烯可以利用由N.I.Yakushkina和I.G.Bolesov在Dehydrohalogenation of onohalogenocyclopropanes as a Method for the Synthesis ofSterically Screened Cyclopropenes,RUSSIAN J.OF ORGANIC CHEM.15:853-59(1979)中描述的方法制备。
本发明的二环丙烯化合物包括式I的那些:
其中:
m和n独立地为从0到4的整数;R1和R2独立地为C1-C20烷基、C2-C20烯基或C2-C20炔基,其中R1或R2中的至少一个是C1-C5烷基、C2-C5烯基或C2-C5炔基。L选自由共价键、磷、氧、硫、镁、C1-C20烷基、C2-C20烯基、C2-C20炔基、C3-C8环烷基、杂环基和芳基组成的组。在一些实施方案中,n和m独立地为1或2。在其他实施方案中,n和m都是0。在其他的实施方案中,L是C1-C6、C6、C1-C12、C12或C4-C10烷基,C4-C8环烷基或C3-C8环烷基。在其他实施方案中,R1或R2中的至少一个是被至少一个选自由以下组成的组中的取代基所取代的烷基、烯基或炔基:卤素,氨基,烷氧基,羧基,烷氧羰基和羟基。在其他的实施方案中,R1或R2中的至少一个中的至少一个碳原子被至少一个选自由以下组成的组中的取代基所取代:酯,腈,胺,胺盐,酸,酸盐,酸的酯,羟基,以及选自氧和氮的杂原子。在一些实施方案中,R1或R2中的至少一个是己基,在其他实施方案中,R1或R2中的至少一个是辛基。
根据本发明的方面,L的一端可连接到位点1、2或3的任一处,L的另一端可连接到位点1’、2’或3’的任一处。在特别的实施方案中,该化合物具有以下结构:
根据本发明的实施方案,该化合物是1,6-二环丙烯基-己烷。在特别的实施方案中,该化合物具有以下结构:
本发明的实施方案进一步包括此处所述的二环丙烯化合物的对映体、立体异构体和盐。
本文中所使用术语“烷基”、“烯基”和“炔基”是指线性或支化的烷基、烯基或炔基取代基,其可以是未取代或取代的。此外,范围如C1-C6的意思是指碳链可以是C1、C2、C3、C4、C5或C6或者所述范围中包含的任意值范围例如C2-C4。本文中所使用的术语“杂环基”、“杂环”或“杂环的”意思是指饱和或部分不饱和的单环、双环或三环基团,其具有3至15个,在一些实例中3至7个原子,并在至少一个环中具有至少一个杂原子。此处所用的“芳基”是指具有6至15个,在一些实例中6至10个环原子的单一或稠合碳环体系的芳香基团,包括取代的芳香基团。芳基的实例包括但不限于苯基、1-萘基、2-萘基和苄基。此处所用的术语“卤素”、“卤”或“卤化物”相应地是指氟代、氟或氟化物,氯代、氯或氯化物,溴代、溴或溴化物,或者碘代、碘或碘化物。
本发明的实施方案进一步包括组合物,其包括以下物质,或者基本上由或由以下物质构成:(a)至少一种式I化合物,或其对映体、立体异构体或盐:
其中m和n独立地为从0到4的整数;R1和R2独立地为C1-C20烷基、C2-C20烯基或C2-C20炔基,其中R1或R2中的至少一个是C1-C5烷基、C2-C5烯基或C2-C5炔基。L选自由共价键、磷、氧、硫、镁、C1-C20烷基、C2-C20烯基、C2-C20炔基、C3-C8环烷基、杂环基和芳基组成的组。和(b)辅助剂例如农业上可接受的载体。
包含本文所述的二环丙烯化合物的农业组合物也被本发明包括。在一些实施方案中,组合物包括0.005重量%至99重量%;在其他的实施方案中1重量%至95重量%;在进一步实施方案中2重量%至90重量%;在更进一步实施方案中3重量%至80重量%;在一些实施方案中4重量%至70重量%的本发明的活性化合物。除非另有规定,否则本文所用的所有的百分比都是重量百分比,所有份都是重量份,并且包括端点和是可组合的。所有的比例以重量计,所有的比例范围都包括端点和是可组合的。所有摩尔范围都包括端点和是可组合的。
这些组合物可包括种一种或多种辅助剂例如载体、增量剂、结合剂、润滑剂、表面活性剂和/或分散剂、润湿剂、扩散剂、分散剂、粘着剂、粘合剂、消泡剂、增稠剂和乳化剂。这些辅助剂是本领域中常用的,可以在John W.McCutcheon,Inc.publication Detergents and Emulsifiers,Annual,Allured PublishingCompany,Ridgewood,N.J.,U.S.A.中找到。术语“农业上可接受的载体”是指通常在农业制剂技术中使用的辅助剂。
许多有机溶剂可作为本发明的活性化合物的载体,例如烃类如己烷、苯、甲苯、二甲苯、煤油、柴油、燃料油和石脑油,酮类如丙酮、甲基乙基酮和环己酮,氯代烃类如四氯化碳,酯类如乙酸乙酯、乙酸戊酯和乙酸丁酯,醚类例如乙二醇单甲醚和二甘醇单甲醚,醇类例如乙醇、甲醇、异丙醇、戊醇、乙二醇、丙二醇、丁基卡必醇乙酸酯和甘油。
水和有机溶剂的混合物,无论作为溶液或乳液,都可用作活性化合物的惰性载体。
本发明的活性化合物的还可以包括辅助剂或载体如滑石、叶腊石、合成细硅胶、凹凸棒土(镁质粘土)、硅藻土(kieselguhr)、白垩、硅藻土(diatomaceous earth)、石灰、碳酸钙、膨润土、漂白土、棉子皮、小麦粉、黄豆粉浮石、硅土、木粉、核桃壳粉、红木粉和木质素。
在本发明的组合物中混入润湿剂可能是合适的。这种润湿剂既可被用于固体组合物,也可被用于液体组合物。润湿剂可以是阴离子、阳离子或非离子性的。
润湿剂的典型种类包括烷基磺酸盐类、烷基芳基磺酸盐、烷基硫酸盐、烷基酰胺磺酸盐、烷基芳基聚醚醇、多元醇的脂肪酸酯和这些酯的烯化氧加成产物、和长链硫醇与烯化氧的加成产物。这种润湿剂的典型实例包括在烷基上有10至18个碳原子的烷基苯磺酸钠盐,烷基酚环氧乙烷缩合产物例如对-异辛基苯酚与10个环氧乙烷单位的缩合产物,皂例如硬脂酸钠和油酸钾,丙基萘磺酸(二-2-乙基己基)的钠盐,磺基琥珀酸钠盐的酯,十二烷基硫酸钠,硬脂酸钠和油酸钾,椰子脂肪酸的磺化单甘油酯的钠盐,山梨聚糖,倍半油酸酯,十二烷基三甲基氯化铵,十八烷基三甲基氯化铵,聚乙二醇十二烷基醚,脂肪酸和松香酸的聚乙烯酯(例如,7和13,可从Akzo Nobel Chemicals,Inc.of Chicago,Illinois商购获得),N-甲基-N-油基牛磺酸钠,土耳其红油,二丁基萘磺酸钠,木质素磺酸钠(N,可从LignoTech USA of Rothschild,Wisconsin商购获得),聚乙二醇硬脂酸酯,十二烷基苯磺酸钠,叔十二烷基聚乙二醇硫醚,长链环氧乙烷-环氧丙烷缩合产物(例如,61(分子量1,000),可从BASF ofMount Olive,NJ商购获得),山梨聚糖倍半油酸酯,妥尔油酸聚乙二醇酯,辛基苯氧乙氧乙基硫酸钠,聚氧乙烯(20)山梨聚糖单月桂酸酯(20,可从ICIAmericas Inc.of Wilmington,Delaware商购获得),三(聚氧乙烯)山梨聚糖单硬脂酸酯(60,可从ICI Americas Inc.of Wilmington,Delaware商购获得),和磺基琥珀酸二己酯钠。固体、液体和气体制剂可通过各种常规方法制备。因此,如果活性成分是固体,则其细碎形式可与细碎的固体载体一块转动混合。作为选择,以液态形式存在的活性成分,包括其混合物、溶液、分散液、乳液和悬浮液,可与细碎形式的固体载体混合。此外,固体形式的活性成分可与液体载体混合形成混合物、溶液、分散液、乳液或悬浮液等。
本发明的实施方案进一步包括抑制植物中乙烯响应的方法,该方法包括以下步骤,或者基本上由或由以下步骤组成:将有效的乙烯响应-抑制量的至少一种式I化合物或者其对映体、立体异构体或盐应用于植物:
其中m和n独立地为从0到4的整数;R1和R2独立地为C1-C20烷基、C2-C20烯基或C2-C20炔基,其中R1或R2中的至少一个是C1-C5烷基、C2-C5烯基或C2-C5炔基。L选自由共价键、磷、氧、硫、镁、C1-C20烷基、C2-C20烯基、C2-C20炔基、C3-C8环烷基、杂环基和芳基组成的组。
在特别的实施方案中,该化合物具有以下结构:
本发明的活性化合物可通过各种适当的方法应用于植物。例如,活性化合物可以气体、液体或固体形式或其任意组合的混合物通过使要处理的植物与化合物接触而单独应用。此外,活性化合物可转换成盐的形式,然后应用到植物。作为选择,可以形成包含一种或多种本发明活性化合物的组合物。组合物可以气体、液体或固体形式或任意组合的混合物通过使要处理的植物与组合物接触而应用。这种组合物可包括惰性载体。适合的固体载体包括粉尘。同样,当为气体形式时,化合物可分散在惰性气体载体中来提供气溶体。该活性化合物也可悬浮在可作为惰性载体的液体溶液如有机溶剂或水溶液中。含有活性化合物的溶液可以是不均一的或均一的,可以是包括混合物、分散液、乳液和悬浮液等的各种形式。
活性化合物及其组合物也可以例如通过使用压缩气体如氮气、二氧化碳、二氯二氟甲烷、三氯氟甲烷或其他卤代烃使它们分散在空气中而作为烟雾剂应用。
因此,在一些实施方案中,本发明的方法可以通过使气体形式的本文所述二环丙烯化合物与植物接触、用包含本文所述二环丙烯化合物的溶液喷雾植物和/或使植物与包括本文所述二环丙烯化合物的固体接触来实施。
本发明可以用来缓和各种不同的乙烯响应。乙烯响应可以由内源性或外源性的乙烯源引起。乙烯响应包括例如花卉、水果和蔬菜的成熟和/或衰老,叶、花和果的脱落,观赏植物如盆栽、切花、灌木和休眠幼苗的寿命缩短,一些植物(例如,豌豆)中的生长抑制,和其他植物(例如,水稻)中的生长刺激。可以由本发明的活性化合物抑制的另外的乙烯响应或乙烯类响应包括但不限于植物生长素活性、终端生长抑制、顶端优势控制、分支增加、分蘖增加、改变植物的生物化学组成(如相对于茎面积增加叶面积)、开花或果实发育的败育或抑制、倒伏作用、刺激种子萌发和中止休眠、和激素或偏上性作用。因此,在一些实施方案中,本文所述二环丙烯化合物抑制以下中的一种或多种:花卉、水果和蔬菜的成熟或衰老;叶、花和水果的脱落;观赏植物、切花、灌木、种子或休眠幼苗的寿命缩短;生长抑制;生长刺激;植物生长素活性;终端生长抑制;顶端优势控制;分支增加;分蘖增加;改变植物形态;改进对植物病原体如真菌的易感性;改变生物化学组成;诱导耐虫性;开花或果实发育的败育或抑制;倒伏作用;刺激种子萌发;中止休眠;激素作用;和偏上性影响。在一些实施方案中,植物是整株植物或其任何部分、大田作物、园林植物、盆栽、切花、或者收获的水果或蔬菜。
一些实施方案中的乙烯响应是果实成熟、蔬菜成熟和/或花卉衰老。
在一些实施方案中,化合物可以应用于封闭或开放的系统。在一些实施方案,化合物可以作为气体用于封闭的系统例如室内,或应用于容器或温室中的植物。在其他的实施方案中,化合物可以作为盐使用,所述盐可以用于例如喷雾、开放的系统如室外例如大田作物或包括花的园林植物。
术语“植物”在此处以一般意义使用,其包括木本的植物如乔木和灌木。用本文所述方法处理的植物包括整株植物和其任何部分、大田作物、园林植物、盆栽、切花(茎和花)以及收获的水果和蔬菜。因此,植物包括农产品如新鲜农产品和园林植物如乔木、灌木、盆栽及观赏植物。
通过本发明的方法用化合物或组合物处理植物优选用对植物无毒害量的活性化合物处理。
可由本发明的方法处理以抑制乙烯响应如成熟和/或衰老的蔬菜包括绿叶蔬菜如莴苣(例如,Lactuea sativa)、菠菜(Spinaca oleracea)和甘蓝(Brassica oleracea),各种块根例如马铃薯(Solanum tuberosum)和胡萝卜(Daucus),鳞茎如洋葱(Alliumsp.),药草如罗勒(Ocimum basilicum)、牛至(Origanum vulgare)、莳萝(Anethumgraveolens),以及大豆(Glycine max),利马豆(Phaseolus limensis),豌豆(Lathyrusspp.),玉米(Zea mays),椰菜(Brassica oleracea italica),花椰菜(Brassica oleraceabotrytis)和芦笋(Asparagus officinalis)。
可由本发明的方法处理以抑制乙烯响应如成熟的水果包括番茄(Lycopersicon esculentum),苹果(Malus domestica),蕉(Musa sapientum),梨(Pyruscommunis),木瓜(Carica papaya),芒果(Mangifera indica),桃(Prunus persica),杏(Prunus armeniaca),油桃(Prunus persica nectarina),柑桔(Citrus sp.),柠檬(Citruslimonia),酸橙(Citrus aurantifolia),葡萄柚(Citrus paradisi),柑橘(Citrus nobilisdeliciosa),猕猴桃(Actinidia chinenus),瓜类如罗马甜瓜(C.cantalupensis)和甜瓜(C.melo),菠萝(Aranas comosus),柿子(Diospyros sp.),各种小型水果包括浆果如草莓(Fragaria)、蓝莓(Vaccinium sp.)和山莓(如,Rubus ursinus),青豆(Phaseolusvulgaris),黄瓜属成员如黄瓜(C.sativus),和鳄梨(Persea americana)。
可由本发明的方法处理以抑制乙烯响应如衰老和/或缩短花卉寿命并由此延长花卉寿命和外观(如,延迟萎蔫)的观赏植物包括盆栽观赏植物和切花。可由本发明的方法处理的盆栽观赏植物和切花包括杜鹃(Rhododendron spp.),八仙花(Macrophylla hydrangea),芙蓉(Hibiscus rosasanensis),金鱼草(Antirrhinum sp.),一品红(Euphorbia pulcherima),仙人掌(例如,Cactaceae schlumbergera truncata),秋海棠(Begonia sp.),玫瑰(Rosa spp.),郁金香(Tulipa sp.),水仙(Narcissus spp.),蒲公英(Taraxacum offinale),矮牵牛(Petunia hybrida),康乃馨(Dianthuscaryophyllus),百合(例如,Lilium sp.),剑兰(Gladiolus sp.),六出花(Alstoemeriabrasiliensis),银莲花(例如,Anemone blanda),耧斗菜(Aquilegia sp.),楤木(例如,Aralia chinensis),紫菀(例如,Aster carolinianus),九重葛(Bougainvillea sp.),山茶(Camellia sp.),风铃草(Campanula sp.),鸡冠花(celosia sp.),桧木(Chamaecyparissp.),菊花(Chrysanthemum sp.),铁线莲(Clematis sp.),仙客来(Cyclamen sp.),小苍兰(例如,Freesia refracta),和Orchidaceae科的兰花。
可由本发明的方法处理以抑制乙烯响应如叶、花和果脱落的植物包括棉花(Gossypium spp.),苹果树,梨树,樱桃树(Prunus avium),美洲山核桃树(Carvaillinoensis),葡萄树(Vitis vinifera),橄榄树(如,Vitis vinifera和Olea europaea),咖啡树(Coffea arabica),食荚菜豆(Phaseolus vulgaris),和垂叶榕(ficus benjamina),以及休眠幼苗如各种果树包括苹果树、观赏植物、灌木和树的幼苗。此外,可根据本发明的方法处理以抑制乙烯响应如叶子脱落的灌木包括女贞(Ligustrumsp.),石楠(Photinia sp.),冬青(Ilex sp.),Polypodiaceae科的蕨类,鹅掌柴(Schefflerasp.),万年青(Aglaonema sp.),枸子(Cotoneaster sp.),伏牛花(Berberis sp.),南部杨梅(Myrica sp.),六道木(Abelia sp.),金合欢(Acacia sp.)和Bromeliaceae科的凤梨。
可由本发明的方法处理的大田作物包括多种或至少一种以上的乔木、灌木、矮树、植物等,包括本文讨论的蔬菜、水果、观赏植物和植物。
已出乎意料地证明,本发明的活性化合物即使以低浓度在不同温度下使用,也是对植物、水果和蔬菜有效的乙烯抑制剂。除其他事项外,本发明的化合物可能会导致比现有技术中发现的化合物更长的乙烯不敏感时间。即使本发明化合物以比现有技术中的化合物更低的浓度在不同的温度下应用和/或作为气体或喷雾应用时,也可能产生该更长的乙烯不敏感时间。
本发明用以下非限制性实施例进行了更加详细解释。在这些实施例中,μl意为微升;ml意为毫升;nl意为纳升;l意为升;cm意为厘米;温度以摄氏度给出。
实施例1
二环丙烯化合物的一般制备过程
二环丙烯化合物可以通过使用对Al Dulayymi等人(1996和1997)的改进过程而制备。所有适当的原料都可以商购获得,也可以很容易地通过本领域普通技术人员制备。适当的起始原料可以在50%NaOH的存在下与溴仿反应,并随后与甲基锂反应以提供所希望的二环丙烯化合物。(参见Al Dulayymi J.R.等人,Structure based interference with insect behaviour-Cyclopropenes analogs ofpheromones containing Z-Alkenes,Tetrahedron,52,12509-12520(1996);AlDulayymi A.R.等人,Simple four and five carbon cyclopropane and cyclopropenesynthetic intermediates,Russian.J.Org.Chem,33,798-816(1997);Al Dulayymi J.R.等人,Synthesis of Putative ~6-,12 and~15- Desaturase Inhibitors,Tetrahedron,53,1099-1110(1997))。
实施例2
1,6-二环丙烯基-己烷的制备
1,9-癸二炔(CAS登记号:1720-38-3)用作原料,它通过使用Couseau,J,Synthesis,805-806(1980)的过程被溴化以提供中间体化合物2,9-二溴-癸-1,9-二烯。然后,通过使用Dulayymi,JR等人Tetrahedron,53,1099-1110(1997)和Dulayymi,JR等人Tetrahedron,52,12509-12520,(1996)的生产过程,2,9-二溴-癸-1,9-二烯与溴仿和NaOH反应,并随后与甲基锂反应,以提供1,6-二环丙烯基-己烷。
实施例3
1,6-二环丙烯基-己烷对豌豆植物生长的影响
合成1,6-二环丙烯基-己烷,并发现其表现出如图1所示的显著的抗乙烯活性。图1(左)显示在1ppm乙烯的存在下豌豆植物的生长。图1(右)显示在1ppm乙烯和1,6-二环丙烯基-己烷两者存在下豌豆植物的生长。1,6-二环丙烯基-己烷被证明是挥发性的,在不同温度下有效工作,当被用作气体时在0.3nL L-1下是活性的和/或保护香蕉免受乙烯响应达至少约42天。
上述实施方案和实施例是对本发明的说明,其并不构成对本发明的限制。本发明被以下权利要求书所限定,权利要求的等价物也包括于其中。
Claims (14)
1.6-二环丙烯基-己烷,或者其立体异构体或盐。
2.具有如下结构的化合物,或者其立体异构体或盐:
3.一种组合物,所述组合物包括:
(a)至少一种1,6-二环丙烯基-己烷,或者其立体异构体或盐;和
(b)辅助剂。
4.权利要求3的组合物,其中该辅助剂是农业上可接受的载体。
5.—种抑制植物中乙烯响应的方法,包括将有效的乙烯-响应抑制量的至少一种如权利要求1或2所述的化合物应用到该植物。
6.权利要求5的方法,其中通过使所述植物与所述化合物的气体、盐或其混合物接触进行应用。
7.权利要求5的方法,其中通过将包含所述化合物的溶液喷雾到所述植物或者使所述植物与包含所述化合物的固体接触进行应用。
8.权利要求5的方法,其中通过施用包含所述化合物的喷雾进行应用。
9.权利要求5的方法,其中所述化合物可以在封闭系统或开放系统中应用。
10.权利要求5的方法,其中所述植物是整株植物或者其任何部分,大田作物,园林植物,盆栽,切花,或者已收获的水果或蔬菜。
11.权利要求5的方法,其中该化合物具有如下结构:
或其盐。
12.权利要求11的方法,其中通过使所述植物与所述化合物的气体接触进行应用。
13.—种延长园林植物寿命的方法,包括将有效的乙烯-响应抑制量的包含至少一种1,6-二环丙烯基-己烷或者其立体异构体或盐的喷雾制剂应用到该园林植物。
14.权利要求13的方法,其中所述化合物具有如下结构:
或者其立体异构体或盐。
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