CN1157551A - 施用于植物的可喷涂的成膜活性物质释放体系 - Google Patents
施用于植物的可喷涂的成膜活性物质释放体系 Download PDFInfo
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- CN1157551A CN1157551A CN95194761A CN95194761A CN1157551A CN 1157551 A CN1157551 A CN 1157551A CN 95194761 A CN95194761 A CN 95194761A CN 95194761 A CN95194761 A CN 95194761A CN 1157551 A CN1157551 A CN 1157551A
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Abstract
用于植物的可喷射的成膜活性物质制剂,其特征在于可由其制备的薄膜具有压敏粘附性,不溶于水,且至少可部分生物降解。
Description
本发明涉及一种可喷涂的成膜制剂,尤其是用于向植物体***地施用生物活性物质。
实践中通常用于植物的活性物质剂型为乳状浓缩液、悬浮浓缩液或通过各种不同的喷洒器(sprayer)、喷雾器(sparger)或雾化装置(nebulizing device)(例如喷雾罐)施用的可湿性粉末。然而,由这些常规制剂带来的缺点是在施用期间活性物质发生损耗,导致对环境的污染(空气、土地、水)。这一问题产生的原因有由于喷射液从植物表面流下或滴下,由于雨水将喷射液洗去,以及由于在施用期间喷射液偏移。这些活性物质剂型的缺点还在于其滞留(附着)不充分和植物表面的可湿性差。这些缺点常常影响达到所希望的效果。
过去,曾对克服上述缺点以优化使用喷雾剂作出过努力。根据现有技术,上述努力可综述如下:
1.通过加入不同的物质(如表面活性剂、防干物质、再湿剂、吸湿添加剂、发泡剂以及特别是粘合促进剂)提高喷射液的施用性能。
2.通过静电荷载喷射液显著地促进了对植物表面选择性地定位。
3.通过改变液滴的尺寸、喷射压力和喷射距离,可以提高保留和湿润性能。
然而,这些方法都不能令人满意地解决喷射偏移和环境影响的问题。
为了克服上述缺点,研制了与常规的喷射有所不同的改进的活性物质释放体系。施用于植物茎轴(shoot axis)的储存剂型为扁平状、碎片状、粘附或压敏粘附体系。这些活性物质的施用形式有效地克服了活性物质损耗及导致环境污染的难题;但是由此又产生了大量其他的问题,这些问题主要是由于上述施用而引起的。使用这种办法,定出它们与植物的接触面的尺寸是极其重要的,以便不喷射到植物的所有部分。对于植物而言,它的生长限制了对施用部位的选择,例如对于完全覆盖土地的那些植物,对其施用非常困难。另外,将这些体系施用于表面具有针状物或刺状物的植物时必然是极难办的。
另外,将这些体系施用于厚度过分增长的植物是有问题的;如果载体薄片不具有足够的拉伸性,则在茎周围施用有使植物受到抑制或该体系进入(growinto)茎轴的危险,这会破坏下面的组织层。
最后,施用该类体系相对来说需要花费大量的时间和工作量,不仅在施用时,而且在施用之后,因为当处理完毕必须将它们除去。而且,还有因废物处理而提高成本的问题。
根据上述现有技术,可以概括地说,在降低所需活性物质消耗,减少施用频率以及减小对其它生物体的不良效应等方面已经取得了很大的进步,但是这是在损失其它性能的情况下达到的。
成膜剂型代表另一种活性物质释放体系。有关该体系可参见下列专利:SU1364267,DE2804563,JP66009674和US4923698。
SU1364267涉及基于羧甲基纤维素的成膜剂型,该成膜剂型用于储存农作物,尤其是保存水果和蔬菜。为此,欲储存的农作物经喷洒或浸泡处理,在植物器官的表面形成一层薄膜;由于该薄膜的物理性能,它能使植物不发生不必要的水损耗,因而延长了其储存时间。然而,在该专利文献中没有提到该制剂中含有活性物质。
德国专利DE 2804563揭示了一种含有活性物质的成膜制剂。该专利文献中叙述了一种剂型,它含有驱鸟剂,防止有用的和开花的灌木的芽喂了鸟。这是一种水性聚合物分散体,在制备植物喷射液时,将该分散体与活性物质搅拌在一起;也可以配制成含活性物质的可湿性粉末。
在上述两种情况下,均掺入基质聚合物(如乙酸乙烯基酯或丙烯酸酯的均聚物和共聚物)作为粘附剂。
日本专利文献JP6445100揭示了另一种含有活性物质的成膜剂型。这是一种基于无机活性物质吸收剂(如高岭土、滑石)的驱鼠剂。由于添加聚合物粘合促进剂(如甲基或羧甲基纤维素、聚乙烯醇或脲),导致形成粘附于植物表面的不溶于水的薄膜层,由于它含有驱鼠剂,因此保护植物不受鼠类危害。
US4923698涉及成膜非聚合物的杀虫或抗虫制剂。在该专利文献中提出了一种基于油包水乳状液的剂型,其中除了生物活性物质之外还包括润滑剂。这些润滑剂确保因为油水相的主要部分蒸发形成薄膜而具有使跑动的害虫不能在其表面移动的性能。另外,薄膜中所含的活性物质会大大提高除虫效果,因为这些活性物质直接作用于害虫。
关于成膜可喷射活性物质制剂,它最终涉及技术杂志Hort science(20,50:879-881)和Plant Disease(67:212-214)中的制品,上述文献叙述了这些研究实验应用于植物以控制叶片病害。
这些已知的能形成薄膜的含有活性物质的可喷射剂型一般都具有严重的缺点,即施用后所形成的薄膜只在相对短的时间覆盖植物表面;这是由于其亲水特性。这些剂型不适用于向植物体***地释放活性物质,这是因为它们缺乏持久附着的能力。这些活性物质必须在植物表面保留足够长的时间,以向植物体供给具有足以维持持久的***作用的浓度的活性物质。
并且,向植物施用活性物质不是这些剂型的主要功能,而其主要功能是向植物提供抗害虫的外保护。因此,已知的施用体系在向植物体施用生物活性物质方面不能令人满意地解决上述问题。
所以,寻求生态学上有益的用于植物的容易处理的活性物质储存制剂的园艺学上的愿望,对于现有技术来说仍然是个未解决的问题。
本发明的目的在于提出一种可喷射的含有活性物质的成膜压敏粘附的,水溶性的且至少可部分生物降解的制剂,该制剂理想的是不污染环境,并提供了活性物质释放体系,该体系具有常规喷射体系的优点和所谓受控释放剂型的体系的优点,而避免了它们的缺点。
最令人惊奇的是,该目的是用根据主权利要求中所述的特征表示的活性物质剂型达到的;这完全满足上述要求。在次权利要求中提供了该活性物质剂型的其它基本特征。
使用术语“可喷射的成膜制剂/剂型”表示通过喷射施用之后在所述基体表面形成薄膜的制剂。薄膜的分布形态可以是不同的;它可以是一种连续膜,也可以是以块状分布的不连续膜,还可以处于中间过渡态。
由根据本发明的活性物质剂型制得的薄膜的优点是具有压敏粘附性,不溶于水以及至少可部分生物降解。
具有成膜剂和活性物质载体功能的聚合物是本发明剂型的基本组分。该成膜可喷射的聚合物溶液在人类医学中是已知的。它们被用作伤口包扎以替代纺织品包扎材料和粘附性包扎物,用通俗的语言称作“喷涂膏”。
丙烯酸和/或甲基丙烯酸的酯类(如丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丁酯和甲基丙烯酸甲酯)的均聚物或共聚物被用作制备本发明的剂型的成膜物质。另外,其它适用的聚合物有乙基纤维素丁酸纤维素或乙酸纤维素,以及多羟基丁酸和多羟基戊酸。
本发明的制剂是物理活性物质/聚合物-组合物,它们以溶液或乳状液的形式存在。它们以烟雾剂喷涂在植物表面,溶剂或乳化剂蒸发之后,形成薄的粘附的含有活性物质的水不溶性薄膜。
这些制剂中所含的无毒有机溶剂是高挥发性的。一般来说,它们的沸点为+50℃至180℃。如果可能的话,其沸点应不超过150℃,以避免所形成的薄膜需要不必要长的干燥时间。适用的溶剂包括乙酸乙酯、氯仿、丙酮、乙醇或其混合物。选择溶剂或溶剂混合物的量使得到的制剂具有相对低的粘度,以确保理想喷涂而不形成绳状物。
另外,本发明的制剂必须是能完全烟雾化并在烟雾剂容器中储存期间是稳定的。适用的推进剂包括可液化气体形式的轻质烃类,例如丙烷、丁烷、异丁烷及其混合物。过去经常用作推进剂的卤代烃类将不再使用,这是因为它们对臭氧具有高的潜在破坏性。可以使用氮气、二氧化碳或一氧化二氮作为喷放气体替代轻质烃类。
用作成膜剂和活性物质载体体系的固体混合物的总量为0.5至10%(重量),较好为4至6%(重量),这是相对于含有推进剂的制剂总量而言的。
本发明的活性物质剂型一个重要的优点是形成的薄膜具有压敏粘附性。这有效地减小了现有技术中的严重缺点,即保留不充分。由这些剂型得到的含有活性物质的薄膜较好地显示出持久的粘附性。它们立即且持久地附着在植物表面,这就确保与植物的末端组织紧密接触;这样的接触对于最佳活性物质释放是绝对需要的。尤其是如果需要长期地持续不断地供给活性物质,则该性能显得特别重要。高的粘附能力在施用区域是与温度相对无关的。在该区域内薄膜的稳定性也得到确保。因此,它们适用于在室内及室外施用于植物。
薄膜的压敏粘附性能在施用方面,尤其是在植物保护方面带来了其它的优点。由于这些薄膜具有瞬间粘附能力,因此它们可以用作对众多附着在薄膜表面的破坏性害虫最轻微接触时的机械阻挡层或陷阱。由于这些薄膜含有活性物质,害虫(如真菌孢子或昆虫)立即与活性物质接触,防止了有害作用的发生。
压敏粘附性能可以通过使用适宜的聚合物作为活性物质载体而获得。这主要包括混合的丙烯酸和丙烯酸酯共聚物,尤其是丙烯酸烷基酯(其中烷基含4至12个碳原子),例如丙烯酸2-乙基己酯、丙烯酸正丁酯和丙烯酸异辛酯。
如果使用不具有压敏粘附性的聚合物,则必须加入合适的辅助剂以获得所需的性能。为此主要使用树脂类物质如改性的天然树脂、最重要者有松香及其衍生物、多萜树脂、烃类树脂以及香豆酮-茚树脂。特别适用的是松香酯类(例如Foral85和StaybeliteEster 10),这是因为它们与聚丙烯酸酯具有极佳的相容性。树脂的加入量取决于所需的粘附性能,并有一个上限,这是因为当树脂的比例过高时,所形成的薄膜的粘附性太低。该量可在1.0至20%(重量)范围内变化,通常为5至10%(重量),相对于制剂中固体含量。
本发明制剂的另一个优点是所形成的薄膜不溶于水。这是特别重要的,因为即使在高降雨量期间,该薄膜仍附着于植物表面。因此,在所需的处理期间薄膜的粘附强度不变。
由于所形成的薄膜材料具有疏水性,从而导致耐水性。除了聚丙烯酸酯、聚羟基丁酸酯和羟基丁酸酯-羟基戊酸酯共聚物之外,也可以使用乙基纤维素和丁酸纤维素和乙酸纤维素作为本发明制剂的适宜的成膜组分。并且,它们优异之处是具有生物降解性能,这使它们特别适用于制备本发明的制剂。
由本发明的制剂在植物表面形成的薄膜理想的必须是可生物降解的。这意味着它们受生物活性环境(微生物)作用,部分地或完全分解。该性能是特别有利的,这是因为由于这些薄膜具有良好的压敏粘附性,因此它们可以作为活性物质在植物上保留较长的时间(例如一个植物生长周期),而不必随后除去。通过选择聚合物,可以控制生物降解的程度。因此可以使这些剂型的使用者节省大量的时间和工作量,同时还具有持续供给生物活性的优点。上述性能的这种组合,使本发明制剂明显优于现有技术中所述的活性物质释放体系。
本发明的薄膜中所含的活性物质以受控制的方式释放,该释放是通过扩散而进行的。
可以通过本发明的制剂释放至植物的活性物质是影响动物或植物体内过程的那些活性物质。杀虫剂、杀真菌剂、杀螨剂、杀菌剂以及生长调节剂是最重要的***性活性植物保护剂。
***杀虫剂包括,例如,丁酮威(butocaroxim)、乐果、双氧威、威百亩(methamyl)、杀线威、亚砜吸磷、抗蚜威或残杀威。
***杀真菌剂包括,例如,苯菌灵、糠菌唑、双苯***醇(bitertanole)、乙环唑、氟硅唑(flusilazol)、呋霜灵、乙磷铝、抑霉唑、甲霜灵、戊菌唑、丙环唑、噻菌灵(thiabendazol)、***酮、***醇或嗪氨灵。
***杀螨剂包括,例如,四螨嗪(clofentizine)、苯丁锡和噻螨酮。
***生长调节剂包括,例如,乙烯利和β-吲哚乙酸(IAA)。
***杀菌剂包括,例如,氟甲喹。
而且,本发明的制剂可以包括在植物中不发生***作用,但留存在植物表面,因而作用于有害物的活性物质。例如,可以将属于二硫代氨基甲酸酯的接触杀真菌剂(如代森锰、代森锌或代森锰锌)引入本发明的制剂中,以保护植物表面不受局部真菌的感染(导致霉变的真菌,导致叶片出现斑点的生物体,各种锈病)。
驱鸟剂和驱虫剂代表另一类生物活性物质的应用实例,该类生物活性物质不通过植物发挥作用。它们也可以通过本发明的制剂施用于植物表面,由此可作用于相应的有害物。
在本发明的制剂中活性物质可以单独存在,也可以混合物的形式存在。可以将它们溶解或分散在聚合物基质中。本发明的剂型的较佳实例中含有下列组分:
a)1.0至10.0%(重量)固体,该固体包括0.5至8.0%(重量)至少一种聚合物,0.5至5.0%(重量)至少一种活性物质,0.0至2.0%(重量)剂型助剂,相对于制剂的总重量,
b)0.5至80%(重量)至少一种挥发性有机溶剂,
c)0.5至80%(重量)至少一种液化气体推进剂。
本发明的制剂可以含有渗透增强剂、增粘剂、乳化剂和增塑剂等助剂。这些助剂的功能一方面是以适宜的物理-化学形式向植物供给活性物质,另一方面是使活性物质的固有效力产生最佳效果。
渗透增强剂增加生物活性物质向植物的输导***中的扩散。为此,可以加入下列物质:烷基硫酸盐、烷基磺酸盐、脂肪酸、多价金属的脂肪酸盐、脂肪酸酯、氧化胺、单酸甘油酯、甘油二酯或甘油三酯、长链醇、水杨酸、2-吡咯烷酮衍生物或脲。
粘附性树脂是适宜的增粘剂。特别适宜的有松香酯类(StaybeliteEster 10)和合成烃类(如Escorez1102F)。
适宜的乳化剂包括,例如,高级脂肪醇、不完全脂肪酸酯(partial fatty acidesters)、多价醇、糖类的不完全脂肪酸酯、聚乙二醇脂肪酸酯、聚乙二醇山梨聚糖-脂肪酸酯以及磷脂、季铵化合物和吡啶鎓化合物。
适宜的增塑剂包括低分子量聚乙烯醇、甘油酯、单价醇和多价醇、脂肪或蜡。
本发明的剂型可以用于向植物供给生物活性物质,可以是***作用,也可以是局部作用。植物保护是本发明制剂的较佳应用领域。下面给出的实施例是用于说明本发明。其中提到的任何量、比例和百分比均相对于制剂的总重量(包括推进剂),除非另有说明。
实施例1
将4.5份(重量)分子量为750,000道尔顿的丙烯酸2-乙基己酯/丙烯酸共聚物在加热下溶解在压力容器中,在44份(重量)乙酸乙酯中搅拌。加入0.9份(重量)用作增粘剂的松香树脂(Foral85)之后,将0.6份(重量)活性物质triticonazole分散在所得到的材料中。可将该含有活性物质的聚合物溶液(在25℃时其相对粘度为0.58Pa.s,根据Brookfield LVF/测定体)注入喷雾容器中,同时加入50份(重量)相同量的丁烷、丙烷和异丁烷。
实施例2
将5份(重量)活性物质氯苯嘧啶醇(fenarimole)与5份(重量)N-甲基-2-吡咯烷酮一起加入29.5份(重量)常规得到的混合的聚合物中,该聚合物含有75%(重量)聚丙烯酸2-乙基己酯、15%(重量)聚丙烯酸和10%(重量)聚甲基丙烯酸甲酯,该聚合物以在含有相同份数(重量)的乙酸乙酯和乙醇的溶剂混合物中的48%(重量)的聚合物溶液的形式存在。在连续搅拌下,加入的活性物质均匀地分散在该材料中。加入65%(重量)液态丁烷之后,将该含有活性物质的聚合物溶液注入喷雾容器中。
Claims (10)
1.用于植物的可喷射的成膜活性物质制剂,其特征在于可由其制备的薄膜具有压敏粘附性,不溶于水,且至少可部分生物降解。
2.如权利要求1所述的活性物质制剂,其特征在于它含有下列组分:
a)1.0至10.0%(重量)固体,该固体相对于制剂的总重量,含有0.5至8.0%(重量)至少一种聚合物,0.5至5.0%(重量)至少一种活性物质,0.0至2.0%(重量)剂型助剂,
b)0.5至80%(重量)至少一种挥发性有机溶剂,
c)0.5至80%(重量)至少一种液化气体推进剂。
3.如权利要求1或2所述的活性物质制剂,其特征在于所述聚合物是至少可部分生物降解的,其选自聚丙烯酸酯、取代度≤2的纤维素衍生物,例如纤维素醚、纤维素酯或乙酸丁酸混合酯纤维素,以及羟基丁酸和羟基戊酸的均聚物和共聚物。
4.如权利要求1至3中的一项或多项所述的活性物质制剂,其特征在于它含有渗透增强剂、增粘剂、乳化剂和/或增塑剂作为助剂。
5.如前面权利要求中任何一项所述的活性物质剂型,其特征在于它含有至少一种供给植物的活性物质,所述活性物质属于下列组:
杀虫剂:丁酮威(butocaroxim)、乐果、双氧威、威百亩(methamyl)、杀线威、亚砜吸磷、抗蚜威、残杀威
杀真菌剂:苯菌灵、糠菌唑、双苯***醇(bitertanole)、乙环唑、氟硅唑(flusilazol)、呋霜灵、乙磷铝、抑霉唑、甲霜灵、戊菌唑、丙环唑、噻菌灵(thiabendazol)、***酮、***醇、嗪氨灵
杀菌剂:氟甲喹
杀螨剂:四螨嗪(clofentizine)、苯丁锡、噻螨酮
生长调节剂:乙烯利、β-吲哚乙酸(IAA)。
6.如前面权利要求中任何一项所述的活性物质剂型,其特征在于它含有至少一种供给植物的具有接触作用的活性物质,所述活性物质选自下列组中:
杀真菌剂:二硫代氨基甲酸酯,例如福美锌、代森锌、代森钠、代森锰锌、福美双
驱虫剂:邻苯二甲酸二甲酯、避虫酮、N,N-二乙基-间甲苯甲酰胺。
7.如前面权利要求中任何一项所述的活性物质制剂,其特征在于活性物质的释放是受控制的。
8.如前面权利要求中的一项或多项所述的活性物质剂型用于将活性物质施用于植物。
9.如前面权利要求中的一项或多项所述的活性物质剂型用于在植物表面形成薄层。
10.如前面权利要求中的一项或多项所述的活性物质剂型用作保护膜覆盖在植物表面,且含有活性物质用于防止霉菌感染及被有害物吸入和吞食(voracity)。
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DE4430449A DE4430449C1 (de) | 1994-08-27 | 1994-08-27 | Versprühbare filmbildende Wirkstoffabgabesysteme zur Anwendung an Pflanzen |
DEP4430449.8 | 1994-08-27 |
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US (1) | US6103253A (zh) |
EP (1) | EP0777414B1 (zh) |
JP (2) | JPH10505342A (zh) |
KR (1) | KR970705338A (zh) |
CN (1) | CN1157551A (zh) |
AT (1) | ATE176379T1 (zh) |
AU (1) | AU701110B2 (zh) |
CZ (1) | CZ54097A3 (zh) |
DE (2) | DE4430449C1 (zh) |
ES (1) | ES2130638T3 (zh) |
FI (1) | FI970788A (zh) |
GR (1) | GR3030084T3 (zh) |
HU (1) | HUT76893A (zh) |
IL (1) | IL115046A (zh) |
MX (1) | MX9701488A (zh) |
NO (1) | NO970361D0 (zh) |
NZ (1) | NZ291814A (zh) |
PL (1) | PL318789A1 (zh) |
SK (1) | SK21897A3 (zh) |
WO (1) | WO1996006527A1 (zh) |
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CN107926949A (zh) * | 2017-11-17 | 2018-04-20 | 南京高正农用化工有限公司 | 高强力农药 |
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1995
- 1995-08-12 DE DE59505047T patent/DE59505047D1/de not_active Expired - Lifetime
- 1995-08-12 PL PL95318789A patent/PL318789A1/xx unknown
- 1995-08-12 WO PCT/EP1995/003205 patent/WO1996006527A1/de not_active Application Discontinuation
- 1995-08-12 SK SK218-97A patent/SK21897A3/sk unknown
- 1995-08-12 CN CN95194761A patent/CN1157551A/zh active Pending
- 1995-08-12 ES ES95929858T patent/ES2130638T3/es not_active Expired - Lifetime
- 1995-08-12 CZ CZ97540A patent/CZ54097A3/cs unknown
- 1995-08-12 US US08/809,311 patent/US6103253A/en not_active Expired - Lifetime
- 1995-08-12 AU AU33450/95A patent/AU701110B2/en not_active Ceased
- 1995-08-12 JP JP8508322A patent/JPH10505342A/ja active Pending
- 1995-08-12 JP JP50844296A patent/JP3805361B2/ja not_active Expired - Fee Related
- 1995-08-12 HU HU9701501A patent/HUT76893A/hu unknown
- 1995-08-12 AT AT95929858T patent/ATE176379T1/de active
- 1995-08-12 EP EP95929858A patent/EP0777414B1/de not_active Expired - Lifetime
- 1995-08-12 KR KR1019970701287A patent/KR970705338A/ko not_active Application Discontinuation
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- 1997-01-28 NO NO970361A patent/NO970361D0/no not_active Application Discontinuation
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Cited By (8)
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CN101999345A (zh) * | 2010-10-20 | 2011-04-06 | 周端午 | 绿色、长效抑菌防霉杀虫溶胶制剂 |
CN102659467A (zh) * | 2012-04-12 | 2012-09-12 | 广西田园生化股份有限公司 | 一种含有乙烯利的超低容量液剂 |
CN104145987A (zh) * | 2014-08-08 | 2014-11-19 | 广西大学 | 乙烯利可控缓释材料的制备及应用 |
CN104145987B (zh) * | 2014-08-08 | 2016-06-29 | 广西大学 | 乙烯利可控缓释材料的制备及应用 |
CN104782682A (zh) * | 2015-03-25 | 2015-07-22 | 浙江工业大学之江学院 | 一种环境友好型聚羟基戊酸酯驱蚊片及制备方法 |
CN107926949A (zh) * | 2017-11-17 | 2018-04-20 | 南京高正农用化工有限公司 | 高强力农药 |
CN114052013A (zh) * | 2021-12-14 | 2022-02-18 | 贵州省烟草公司安顺市公司 | 一种用于防治烟草白粉病的药剂组合物 |
CN114052013B (zh) * | 2021-12-14 | 2023-03-10 | 贵州省烟草公司安顺市公司 | 一种用于防治烟草白粉病的药剂组合物 |
Also Published As
Publication number | Publication date |
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NO970361L (no) | 1997-01-28 |
NZ291814A (en) | 1997-11-24 |
ZA957167B (en) | 1996-04-17 |
AU3345095A (en) | 1996-03-22 |
US6103253A (en) | 2000-08-15 |
JPH10505342A (ja) | 1998-05-26 |
NO970361D0 (no) | 1997-01-28 |
HUT76893A (en) | 1997-12-29 |
FI970788A0 (fi) | 1997-02-25 |
EP0777414B1 (de) | 1999-02-03 |
SK21897A3 (en) | 1997-09-10 |
WO1996006527A1 (de) | 1996-03-07 |
FI970788A (fi) | 1997-02-25 |
DE4430449C1 (de) | 1996-02-01 |
ATE176379T1 (de) | 1999-02-15 |
PL318789A1 (en) | 1997-07-07 |
IL115046A (en) | 1999-10-28 |
GR3030084T3 (en) | 1999-07-30 |
EP0777414A1 (de) | 1997-06-11 |
KR970705338A (ko) | 1997-10-09 |
JPH10504830A (ja) | 1998-05-12 |
AU701110B2 (en) | 1999-01-21 |
CZ54097A3 (en) | 1997-06-11 |
JP3805361B2 (ja) | 2006-08-02 |
IL115046A0 (en) | 1995-12-08 |
MX9701488A (es) | 1998-10-31 |
ES2130638T3 (es) | 1999-07-01 |
DE59505047D1 (de) | 1999-03-18 |
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