CN1192682A - 防治寄生性原生动物的组合物 - Google Patents
防治寄生性原生动物的组合物 Download PDFInfo
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- CN1192682A CN1192682A CN96196078A CN96196078A CN1192682A CN 1192682 A CN1192682 A CN 1192682A CN 96196078 A CN96196078 A CN 96196078A CN 96196078 A CN96196078 A CN 96196078A CN 1192682 A CN1192682 A CN 1192682A
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- alkyl
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- replaces
- amino
- carbon atom
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Abstract
本发明涉及取代苯并咪唑与聚醚抗菌素或人工合成的抑球虫剂的混合物,用于防治家畜体内寄生性原生动物。
Description
本发明涉及防治寄生性原生动物(尤其是)球虫及鱼寄生物和昆虫寄生物的组合物，包括取代苯并咪唑与一种聚醚抗菌素或人工合成的抑球虫剂的混合物。
取代苯并咪唑及其用作杀虫剂、杀菌剂和除草剂已经被揭示(EP-OS(欧洲专利公开说明书)87 375、152 360、181 826、239 508、260744、266 984、US-A 3 418 318、3 472 865、3 576 818、3 728994)。
卤代苯并咪唑及其作为蠕虫药、抑球虫剂及农药的效果也已经被揭示(DE-OS(德国专利公开说明书)2 047 369、DE-OS(德国专利公开说明书)4 237 617)。硝基取代的苯并咪唑与聚醚抗菌素混合物用作抑球虫剂也已被揭示(US-A 5 331 003)。然而它们的效果尚不能在所有的情况下均令人满意。
球虫病是由单细胞寄生物(原生动物)引发的一种疾病。特别是在家禽饲养中，它能导致巨大的损失。为了避免发生这种情况，用抑球虫剂对家畜进行预防处理。对所用的组合物的抗性发展仅只在几年后就会产生严重的问题。另一方面，通过使用完全新型的化学抑球虫剂(尤其是组合物)防治甚至具有多种抗药性的寄生物品系是可能的。
本发明涉及作为家畜上防治寄生性原生动物(尤其是球虫)的组合物的混合物，所述的混合物为式(I)的取代苯并咪唑与一种或多种下文中提到的化合物的混合物，其中R1，R2，R3和R4彼此独立地各自代表氢，卤素，代表各任选取代的烷基，烷氧基，烷硫基，烷基亚磺酰基，烷基磺酰基，代表各任选取代的稠合上的二氧亚烷基，但是其中取代基R1，R2，R3和R4中至少有一个不是氢和卤素，R5代表氢，代表烷基，该烷基可以由以下相同或不同的基团取代一次或多次：OH，CN，NH2，烷基，环烷基，链烯基，炔基，烷氧基，卤代烷氧基，烷硫基，卤代烷硫基，链烯氧基，炔氧基，氨基羰基，任选取代的烷基羰基，任选取代的(杂-)芳基羰基，任选取代的烷氧羰基(AlkO-CO-)，任选取代的烷氧基羰基氧基(AlkO COO-)，氨基磺酰基(SO2NH2)，任选取代的单或二烷基氨基磺酰基，酰化氨基(AlkCON(R7)-或AlkOCON(R7)-)，其中R7等同于氢烷基或环烷基，或任选取代的烷基磺酰基氨基(烷基-SO2NH-)，或烷基磺酰基-N-烷基氨基(烷基-SO2-N-烷基)，任选取代的芳基磺酰基氨基(芳基-SO2NH-)或芳基磺酰基-N-烷基氨基(芳基-SO2-NAlk-)，任选取代的二烷基氨基，此外，R5代表任选取代的烷氧基羰基，任选取代的(杂-)芳氧基羰基，烷基磺酰基，链烯基磺酰基，(杂-)芳基磺酰基，或-SO2NR8R9，-CONR8R9-或-P(O)(NR8R9)2，其中R8和R9代表H或任选由一或多个基团取代的烷基，R6代表氟代烷基，上面所述的一或多个化合物为：聚醚类抗菌素(如马度米星，拉沙洛西，莫能菌素，甲基盐霉素，沙利霉素)或合成的抑球虫剂如：氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶鎓氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶+磺胺喹鎓+磺胺喹喔啉 喔啉氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶+磺胺喹鎓+磺胺喹喔啉+4-乙酰氨基-2-乙氧基苯甲酸甲酯 喔啉+4-乙酰氨基-2-
乙氧基苯甲酸甲酯4，4-二硝基对称二苯脲+2-羟基-4，6-二甲基嘧啶 二硝基苯脲3，5-二氯-2，6-二甲基-4-吡啶醇 二氯二甲吡啶酚3，5-二氯-2，6-二甲基-4-吡啶醇+7-苄氧基-6-丁基-1，4- 二氯二甲吡啶酚+苄二氢-4-氧喹啉-3-羧酸甲酯 氧喹甲酯6-正癸氧基-7-乙氧基-4-羟基喹啉-3-羧酸乙酯 癸氧喹酯9-(2-氯-6-氟苯基甲基)-9H-嘌呤-6-胺 阿谱西特(±)-2，6-二氯-α-(4-氯苯基)-4-(4，5-二氢-3，5-二氧代- 苯乙腈，地克珠利1，2，4-三嗪-2(3H)-基)-苯乙腈1-[3-甲基-4-(4’-三氟甲基硫基苯氧基)-苯基]-3-甲基- 托三嗪1，3，5-三嗪-2，4，6(1H，3H，5H)-三酮4，4-二硝基对称二苯脲+2-羟基-4，6-二甲基嘧啶 双氯苄氨胍
[＝nicarbazin]7-溴-6-氯-常山碱 卤夫酮3，5-二硝基-O-甲苯甲酰胺 二硝甲苯酰胺
根据本发明可使用的苯并咪唑类是知道的。它们通常由式(I)定义。优选的式(I)化合物是这样的化合物，其中R1，R2，R3和R4彼此独立地各自代表氢、氟、氯、溴、碘，代表直链或支链烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基，它们各带有1-8个碳原子，代表带有3-8个碳原子的环烷基，代表各是直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基、卤代烷基磺酰基，它们各带有1-6个碳原子和1-13个相同或不同卤原子，代表双连接的带有1-5个碳原子的二氧代亚烷基，它任选相同或不同地由1-10个卤素和/或带有1-4个碳原子的直链或支链烷基和/或带有1-4个碳原子和1-9个卤原子的直链或支链卤代烷基单或多取代，
但是其中取代基R1，R2，R3和R4中至少之一不是氢和卤素，R5代表氢，代表带有1-4个碳原子的烷基，此烷基可以被下列相同或不同的基团取代一次或多次，OH，CN，NH2，带有1-4个碳原子的烷基，带有3-10个碳原子的环烷基，带有2-6个碳原子的链烯基，带有2-6个碳原子的炔基，带有1-6个碳原子的烷氧基，带有1-6个碳原子和1-5个卤原子的卤代烷氧基，带有1-6个碳原子的烷硫基，带有1-6个碳原子和1-5个卤原子的卤代烷硫基，带有2-6个碳原子链烯氧基，带有3-6个碳原子的炔氧基，任选取代的带有1-6个碳原子的烷基羰基，任选取代的苯基-或杂芳基羰基，任选取代的带有1-6个碳原子的烷氧基羰基，任选取代的带有1-6个碳原子的烷氧基羰基氧基，氨基磺酰基(NH2SO2-)，任选取代的带有1-6个碳原子的单-或二烷基氨基磺酰基，带有1-6个碳原子的酰化氨基(AlkOCON(R7)-或(AlkCON(R7)-)，其中R7等同于氢或带有1-6个碳原子的烷基或带有3-8个碳原子的环烷基，任选取代的带有1-6个碳原子的烷基磺酰氨基，任选取代的带有1-6个碳原子的烷基磺酰基-N-烷基氨基，任选取代的苯基磺酰氨基，任选取代的带有1-6个碳原子的苯基磺酰基-N-烷基氨基，任选取代的带有1-8个碳原子的二烷基氨基，此外，R5代表任选取代的带有1-6个碳原子的烷氧基羰基，带有1-6个碳原子的烷基磺酰基或链烯基磺酰基，它们任选被1-13卤原子取代任选取代的苯基磺酰基，任选取代的杂芳基磺酰基，苯氧基羰基或-SO2NR8R9，-CONR8R9或-P(O)(NR8R9)2，其中R8和R9代表氢或带有1-4个碳原子的烷基，它们可以任选由上面提到的R5的基团之一取代，
可提到的任选取代的基团的取代基如下：
卤素，OH，NH2，带有1-6个碳原子的烷基氨基，氰基，硝基，CO2H，各是直链或支链的烷基，烷氧基，烷硫基，烷基亚磺酰基或烷基磺酰基，它们各带有1-6个碳原子，各是直链或支链的卤代烷基，卤代烷氧基，卤代烷硫基，卤代烷基亚磺酰基或卤代烷基磺酰基，它们各带有1-6个碳原子和1-13相同或不同卤原子，各是直链或支链的烷氧基烷基、烷氧基烷氧基、烷酰基、烷氧基羰基或烷基亚氨基烷基，它们在各自的烷基部分带有1-6个碳原子，双连接的具有1-6个碳原子的二氧基亚烷基，它任选由下列相同或不同的基团取代1-6次：卤素和/或直链或支链的带有1-6个碳原子的烷基和/或直链或支链的具有1-6碳原子和1-13个相同或不同卤原子的卤代烷基，或苯基或苯氧基，它们被相同或不同的卤原子和/或带有1-4个碳原子和1-9个相同或不同卤原子的直链或支链烷基取代1-5次，它们本身还可以携带上述的基团。
可以提到的所列基团的酰基基团是下列基团：带有1-6个碳原子的烷氧基羰基，带有1-6个碳原子的烷基羰基，带有1-6个碳原子的烷氧基羰基氧基，带有1-6个碳原子的烷基磺酰基，苯甲酰基(可任选由上面提到的基团之一取代)，带有2-6个碳原子的链烯基羰基。R6代表1-15氟-C1-C7-烷基。
式I化合物的取代基特别优选具有下列含意：R1，R2，R3和R4彼此独立地各自代表氢，氟，氯或溴，代表各是直链或支链的烷基，烷氧基，烷硫基，烷基亚磺酰基，烷基磺酰基(它们各带有1-4个碳原子)，代表带有3-6个碳原子的环烷基，代表各是直链或支链的卤代烷基、卤代烷氧基、卤代烷硫基、卤代烷基亚磺酰基、卤代烷基磺酰基(它们各带有1-4个碳原子和1-9个相同或不同的卤原子，特别是氟和氯)，或代表双连接的带有1-3个碳原子的二氧亚烷基，它任选由下列相同或不同的基团取代一或多次：1-6个卤原子(特别是氟和氯)和/或带有1-4个碳原子的直链或支链烷基和/或带有1-4个碳原子和1-6个卤原子的直链或支链卤代烷基，但是R1，R2，R3和R4中至少之一不是氢和卤素，R5代表氢，代表带有1-3个碳原子的烷基，特别是甲基和乙基，它们由下列基团取代：OH，CN，NH2，带有1-4个碳原子的烷基(特别是甲基或乙基)，带有2-4个碳原子的链烯基，带有2-4个碳原子的炔基，带有1-4个碳原子的烷氧基，特别是如下烷氧基如甲氧基，乙氧基，丙氧基，异丙氧基，带有1-4个碳原子和1-5个卤原子的卤代烷氧基，特别是诸如三氟甲氧基，五氟乙氧基，氟丙氧基，带有1-4个碳原子的烷硫基，带有1-4个碳原子和1-5个卤原子的卤代烷硫基，带有2-4个碳原子的链烯氧基，带有3-4个碳原子的炔氧基，任选取代的带有1-4个碳原子的烷基羰基，任选取代的苯基羰基，任选取代的带有1-4个碳原子的烷氧基羰基，特别是诸如甲氧基羰基，乙氧基羰基，丙氧基羰基，异丙氧基羰基，叔丁氧基羰基，任选取代的带有1-4个碳原子烷氧基羰基氧基，氨基磺酰基(NH2SO2-)，任选取代的带有1-4个碳原子的单-或二烷基氨基磺酰基，带有1-6个碳原子的酰化氨基，其中R7等同于氢或带有1-4个碳原子的烷基或带有3-6个碳原子的环烷基，任选取代的带有1-4个碳原子的烷基磺酰基氨基，任选取代的带有1-4个碳原子的烷基磺酰基-N-烷基氨基，任选取代的苯基磺酰基氨基，任选取代的带有1-4个碳原子的苯基磺酰基-N-烷基氨基，任选取代的带有1-4个碳原子的二烷基氨基，此外，R5代表任选取代的基团，如带有1-4个碳原子烷氧基羰基、带有1-4个碳原子的烷基磺酰基或链烯基磺酰基，它们任选由1-9个卤原子取代，任选取代的苯基磺酰基，任选取代的杂芳基磺酰基，其中杂芳基代表5-或6元杂环，这些杂环可任选由1-4个碳原子的烷基或卤原子或由在R5中列举的取代基取代，或苯氧基羰基或-SO2NR8R9，-CONR8R9或-P(O)(NR8R9)2，其中R8和R9代表氢或带有1-4个碳原子的烷基，它们任选由上面提到的R5的基团之一取代。
可以提到的任选取代基团的取代基如下：
卤素(特别是氟或氯)，OH，NH2，带有1-4个碳原子的烷基氨基，特别是甲氨基，乙氨基，二甲氨基，二乙基氨基，双(三氟甲氨基)，氰基，硝基，CO2H，各是直链或支链的带有1-4个碳原子的烷基，烷氧基，烷硫基，烷基亚磺酰基或烷基磺酰基，特别是甲基，乙基，甲氧基，乙氧基或甲巯基，各是直链或支链的带有1-4碳原子和1-9个相同或不同的卤原子的卤代烷基，卤代烷氧基，卤代烷硫基，卤代烷基亚磺酰基或卤代烷基磺酰基，特别是三氟甲基，五氟乙基，氟氯乙基，三氯乙基，三氟甲氧基，三氯甲氧基，三氟甲基巯基，各是直链或支链的烷氧基烷基，烷氧基烷氧基，特别是甲氧基乙氧基，乙氧基乙氧基，乙氧基乙基，在各自的烷基部分带有1-4个碳原子的烷酰基，烷氧基羰基或烷氧基亚氨基烷基，特别是乙酰基，任选由下列相同或不同的选自卤原子和/或带有1-4个碳原子和1-9个相同或不同卤原子的直链或支链烷基的基团取代一至五次的苯基或苯氧基，特别是苯基或苯氧基，它们本身可以携带上面提到的基团，R6代表1-7氟-C1-C3-烷基。
非常特别优选的式(I)化合物是那些其中取代基具有下列含义的化合物：R1，R2，R3和R4代表氢，卤素，特别是氯或溴，代表各带有1-4个碳原子的直链或支链烷基，烷氧基，烷硫基，烷基亚磺酰基，烷基磺酰基，特别是甲基，甲氧基，甲基硫基，甲基亚磺酰基或甲基磺酰基，代表各带有1-4个碳原子和1-9个相同或不同的氟原子或氯原子的直链或支链卤代烷基，卤代烷氧基，卤代烷硫基，卤代烷基亚磺酰基，卤代烷基磺酰基，特别是三氟甲基，三氟甲氧基，三氟甲硫基，三氟甲基亚磺酰基，三氟甲基磺酰基，代表具有1-2碳原子的双连接的二氧亚烷基，它任选由氟和/或氯原子取代，特别是代表OCH2O，OCH2CH2O，OCF2CF2O，OCF2O，OCCIFCCIFO，R5代表氢，代表甲基或乙基，它们可由下列基团取代：CN，带有1-4碳原子的烷基(特别是甲基)，带有2-4个碳原子链烯基，特别是-CH＝CH2或-CH＝CHMe，带有2-4个碳原子的炔基，特别是-CCH或-CCMe，带有1-4个碳原子的烷氧基，特别是烷氧基诸如甲氧基，乙氧基，丙氧基，异丙氧基，带有3-4个碳原子的炔氧基，特别是-OCH2CCH或-OCH2CCMe，带有1-4个碳原子的烷基羰基，特别是乙酰基，丙酰基，异丙酰基或叔丁酰基，任选取代的苯基羰基，特别是苯甲酰基，任选取代的带有1-4个碳原子的烷氧基羰基，特别是-CO2Me，-CO2Et，-CO2Pr，-CO2i-Pr或-CO2tBu，带有1-6个碳原子的酰基氨基，其中R7等同于氢或带有1-4个碳原子的烷基或带有3-6个碳原子的环烷基，特别是-N(Me)CO2Me，-N(Me)CO2Et，-N(Et)CO2Et，-N(Et)CO2Me，-N(Pr)CO2Et，-N(Bu)CO2Me，-N(t-Bu)CO2Me，-N(Bu)CO2Et，-N(C6H11)CO2Et，-NHCOMe，-NHCOEt或-NHCOPr，任选取代的带有1-4个碳原子的烷基磺酰基氨基，任选取代的烷基磺酰基-N-烷基氨基，特别是-NMeSO2Me，-NEtSO2Et，-NMeSO2Et，-NEtSO2Me，任选取代的苯基磺酰基氨基，任选取代的带有1-4个碳原子的苯基磺酰基-N-烷基氨基，特别是-NMeSO2Ph，-NEtSO2Ph。此外，R5代表任选取代的带有1-4个碳原子的烷氧基羰基，烷基磺酰基或烯基磺酰基基团，特别是MeSO2-，EtSO2-，PrSO2-或CH2＝CMeCH2SO2-，任选取代的苯基磺酰基，特别是苯基磺酰基或2，4，6-三甲基-苯磺酰基，任选取代的杂芳基磺酰基，其中杂芳基代表一个5或6元杂环，它由氟、氯或溴和/或带有1-4个碳原子的烷基(特别是甲基)和/或R5中提到基团取代(特别是MeO2C)取代且含有一至三个相同或不同的杂原子(特别是N、S和/或O)，苯氧基羰基，或-SO2NR8R9，-CONR8R9或-PO(NR8R9)2，其中R8和R9代表氢或带有1-4个碳原子的烷基，它们任选由上面提到的R5的基团之一取代，特别是代表-SO2NMe或-SO2NEt2，PO(NMe2)2，CONMe2或CONiPr2，R6代表CF3，CHF2或C2F5。
可以具体提到下列的式(I)的取代的苯并咪唑：
可以特别提到的来自取代的苯并咪唑系列的特别优选的化合物是：
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 1 | H | Br | CF3 | H | H | CF3 |
| 2 | H | Br | CF3 | H | CH2CN | CF3 |
| 3 | H | CF3 | Br | H | CH2CN | CF3 |
| 4 | H | Br | CF3 | H | CH2OEt | CF3 |
| 5 | H | CF3 | Br | H | CH2OEt | CF3 |
| 6 | H | Br | CF3 | H | CH2OiPr | CF3 |
| 7 | H | CF3 | Br | H | CH2OiPr | CF3 |
| 8 | H | Br | CF3 | H | CH2COMe | CF3 |
| 9 | H | CF3 | Br | H | CH2COMe | CF3 |
| 10 | H | Br | CF3 | H | CH2OCH(CH2F)2 | CF3 |
| 11 | H | CF3 | Br | H | CH2OCH(CH2F)2 | CF3 |
| 12 | H | Br | CF3 | H | CH2N(Me)CO2Me | CF3 |
| 13 | H | CF3 | Br | H | CH2N(Me)CO2Me | CF3 |
| 14 | H | Br | CF3 | H | CH2N(Bu)CO2Et | CF3 |
| 15 | H | CF3 | Br | H | CH2N(Bu)CO2Et | CF3 |
| 16 | H | Br | CF3 | H | CH2N(t-Bu)CO2Et | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 17 | H | CF3 | Br | H | CH2N(t-Bu)CO2Et | CF3 |
| 18 | H | Br | CF3 | H | CH2N(C6H11)-CO2Et | CF3 |
| 19 | H | CF3 | Br | H | CH2N(C6H11)-CO2Et | CF3 |
| 20 | H | Cl | CF3 | H | H | CF3 |
| 21 | H | Cl | CF3 | H | CH2CN | CF3 |
| 22 | H | CF3 | Cl | H | CH2CN | CF3 |
| 23 | H | Cl | CF3 | H | CH2OEt | CF3 |
| 24 | H | CF3 | Cl | H | CH2OEt | CF3 |
| 25 | H | Cl | CF3 | H | CH2COMe | CF3 |
| 26 | H | CF3 | Cl | H | CH2COMe | CF3 |
| 27 | H | Cl | CF3 | H | CH(Me)COMe | CF3 |
| 28 | H | CF3 | Cl | H | CH(Me)COMe | CF3 |
| 29 | H | Cl | CF3 | H | CH2COtBu | CF3 |
| 30 | H | CF3 | Cl | H | CH2COtBu | CF3 |
| 31 | H | Cl | CF3 | H | CH2COPh | CF3 |
| 32 | H | CF3 | Cl | H | CH2COPh | CF3 |
| 33 | H | Cl | CF3 | H | CH2CCH | CF3 |
| 34 | H | CF3 | Cl | H | CH2CCH | CF3 |
| 35 | H | Cl | CF3 | H | CH2NHCOMe | CF3 |
| 36 | H | CF3 | Cl | H | CH2NHCOMe | CF3 |
| 37 | H | Cl | CF3 | H | CH2N(tBu)CO2Me | CF3 |
| 38 | H | CF3 | Cl | H | CH2N(tBu)CO2Me | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 39 | H | Cl | CF3 | H | CH2N(Me)CO2Me | CF3 |
| 40 | H | CF3 | Cl | H | CH2N(Me)CO2Me | CF3 |
| 41 | H | CF3 | Cl | H | CH2N(Et)CO2Me | CF3 |
| 42 | H | Cl | CF3 | H | CH2N(Et)CO2Me | CF3 |
| 43 | H | CF3 | Cl | H | CH2N(Me)SO2Ph | CF3 |
| 44 | H | Cl | CF3 | H | CH2N(Me)SO2Ph | CF3 |
| 45 | H | CF3 | Cl | H | CH2N(Me)SO2Me | CF3 |
| 46 | H | Cl | CF3 | H | CH2N(Me)SO2Me | CF3 |
| 47 | H | SOCF3 | Cl | H | H | CF3 |
| 48 | H | SO2CF3 | Cl | H | H | CF3 |
| 49 | H | OCF3 | Cl | H | H | CF3 |
| 50 | H | OCF3 | Cl | H | CH2N(Bu)CO2Et | CF3 |
| 51 | H | Cl | OCF3 | H | CH2N(Bu)CO2Et | CF3 |
| 52 | H | OCF3 | Cl | H | CH2N(Pr)CO2Et | CF3 |
| 53 | H | Cl | OCF3 | H | CH2N(Pr)CO2Et | CF3 |
| 54 | H | OCF3 | Cl | H | CH2N(Me)CO2Me | CF3 |
| 55 | H | Cl | OCF3 | H | CH2N(Me)CO2Me | CF3 |
| 56 | H | OCF3 | Cl | H | CH2CN | CF3 |
| 57 | H | Cl | OCF3 | H | CH2CN | CF3 |
| 58 | H | Br | OCF3 | H | H | CF3 |
| 59 | H | Br | OCF3 | H | CH2CN | CF3 |
| 60 | H | OCF3 | Br | H | CH2CN | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 61 | H | Br | OCF3 | H | CH2OEt | CF3 |
| 62 | H | OCF3 | Br | H | CH2OEt | CF3 |
| 63 | H | OCF3 | Br | H | SO2NMe2 | CF3 |
| 64 | H | Br | OCF3 | H | CH2N(Me)CO2Me | CF3 |
| 65 | H | OCF3 | Br | H | CH2N(Me)CO2Me | CF3 |
| 66 | H | Br | OCF3 | H | CH2N(Et)CO2Et | CF3 |
| 67 | H | OCF3 | Br | H | CH2N(Et)CO2Et | CF3 |
| 68 | H | Br | OCF3 | H | CH2N(Me)CO2Et | CF3 |
| 69 | H | CF3O | OCH3 | H | H | CF3 |
| 70 | H | CF3 | OCH3 | H | H | CF3 |
| 71 | H | OCF3 | OCF3 | H | SO2NMe2 | CF3 |
| 72 | H | CF3O | OCF3 | H | CH2OCH2CCH | CF3 |
| 73 | H | OCF2O | H | H | CF3 | |
| 74 | H | OCF2CF2O | H | H | CF3 | |
| 75 | H | OCF2CF2O | H | H | CHF2 | |
| 76 | H | OCF2CF2O | H | H | C2F5 | |
| 77 | H | OCF2CF2O | H | CH2CN | CF3 | |
| 78 | H | OCF2CF2O | H | CH2OEt | CF3 | |
| 79 | H | OCF2CF2O | H | CH2OiPr | CF3 | |
| 80 | H | OCF2CF2O | H | CH2N(Me)CO2Et | CF3 | |
| 81 | H | OCF2CF2O | H | CH2N(Me)CO2Me | CF3 | |
| 82 | H | OCF2CF2O | H | CH2N(C6H11)CO2Et | CF3 | |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 83 | H | OCF2CF2O | H | CH2N(C6H11)COEt | CHF2 | |
| 84 | H | OCFHCF2O | H | H | CF3 | |
| 85 | H | O(CCIF)2O | H | H | CF3 | |
| 86 | H | O(CCIF)2O | H | CH2OEt | CF3 | |
| 87 | H | O(CCIF)2O | H | CH2N(Me)CO2Et | CF3 | |
| 88 | H | O(CCIF)2O | H | CH2CN | CF3 | |
| 89 | H | O(CH2)2O | H | CH2OEt | CF3 | |
| 90 | Cl | H | SO2CF3 | H | H | CF3 |
| 91 | Cl | H | SO2CF3 | H | H | CHF2 |
| 92 | Br | H | CF3 | H | CH2COtBu | CF3 |
| 93 | Br | H | CF3 | H | CH2OEt | CF3 |
| 94 | Br | H | CF3 | H | CH2CO2Bu | CF3 |
| 95 | Br | H | CF3 | H | CH2N(Me)CO2Me | CF3 |
| 96 | Br | H | CF3 | H | CH2CH＝CH2 | CF3 |
| 97 | Br | H | CF3 | H | H | CF3 |
| 98 | Br | H | CF3 | H | CH2N(iPr)CO2Et | CF3 |
| 99 | Br | H | CF3 | H | CH2N(C6H11)CO2Et | CF3 |
| 100 | Br | H | SO2Me | H | H | CF3 |
| 101 | Br | H | SO2CF2 | H | H | CF3 |
| 102 | CF3 | H | Cl | H | H | CF3 |
| 103 | CF3 | H | Cl | H | CH2CN | CF3 |
| 104 | CF3 | H | Cl | H | CH2COPh | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 105 | CF3 | H | Cl | H | CH2OEt | CF3 |
| 106 | CF3 | H | Cl | H | CH2N(Me)CO2Me | CF3 |
| 107 | CF3 | H | Cl | H | CH2N(Me)CO2Et | CF3 |
| 108 | CF3 | H | Cl | H | CH2N(tBu)CO2Et | CF3 |
| 109 | CF3 | H | Cl | H | CH2N(Bu)CO2Et | CF3 |
| 110 | CF3 | H | Cl | H | CH2N(Et)CO2Et | CF3 |
| 111 | CF3 | H | Cl | H | CH2N(C6H11)CO2Et | CF3 |
| 112 | CF3 | H | Br | H | H | CF3 |
| 113 | CF3 | H | Br | H | H | CHF2 |
| 114 | CF3 | H | Br | H | CH2CN | CF3 |
| 115 | CF3 | H | Br | H | CH2N(Me)SO2Me | CF3 |
| 116 | CF3 | H | Br | H | CH2OPr | CF3 |
| 117 | CF3 | H | Br | H | CH2N(Me)CO2Me | CF3 |
| 118 | CF3 | H | Br | H | CH2N(Pr)CO2Et | CF3 |
| 119 | CF3 | H | Br | H | CH2N(Et)CO2Et | CF3 |
| 120 | CF3 | H | Br | H | CH2N(C6H11)CO2Et | CF3 |
| 121 | CF3 | H | CF3 | H | H | CF3 |
| 122 | CF3 | H | CF3 | H | H | CHF2 |
| 123 | CF3 | H | CF3 | H | CH2CN | CF3 |
| 124 | CF3 | H | CF3 | H | CH2N(Et)CO2Et | CF3 |
| 125 | CF3 | H | CF3 | H | CH2N(Pr)CO2Et | CF3 |
| 126 | CF3 | H | CF3 | H | CH2N(C6H11)CO2Et | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 166 | H | OCF2CF2O | H | SO2CH3 | CF3 | |
| 167 | H | OCF2CF2O | H | PO-(N(CH3)2)2 | CF3 | |
| 168 | H | Br | CF3 | H | CO-OCH(CH3)2 | CF3 |
| 169 | H | Br | CF3 | H | CO2N(CH3)2 | CF3 |
| 170 | H | Br | CF3 | H | PO-(N(CH3)2)2 | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 1 | H | Br | CF3 | H | H | CF3 |
| 2 | H | Br | CF3 | H | CH2CN | CF3 |
| 3 | H | CF3 | Br | H | CH2CN | CF3 |
| 4 | H | Br | CF3 | H | CH2OEt | CF3 |
| 5 | H | CF3 | Br | H | CH2OEt | CF3 |
| 58 | H | Br | OCF3 | H | H | CF3 |
| 59 | H | Br | OCF3 | H | CH2CN | CF3 |
| 60 | H | OCF3 | Br | H | CH2CN | CF3 |
| 74 | H | OCF2-CF2O | H | H | CF3 | |
| 83 | H | OCF2-CF2O | H | CH2N(C6H11)-CO2Et | CF3 | |
| 92 | Br | H | CF3 | H | CH2COtBu | CF3 |
| 95 | Br | H | CF3 | H | CH2N(Me)CO2Me | CF3 |
| 96 | Br | H | CF3 | H | CH2CH＝CH2 | CF3 |
| 99 | Br | H | CF3 | H | CH2N(C6H11)-CO2Et | CF3 |
| 102 | CF3 | H | Cl | H | H | CF3 |
| No. | R1 | R2 | R3 | R4 | R5 | R6 |
| 103 | CF3 | H | Cl | H | CH2CN | CF3 |
| 105 | CF3 | H | Cl | H | CH2OEt | CF3 |
| 107 | CF3 | H | Cl | H | CH2N(Me)CO2Et | CF3 |
| 108 | CF3 | H | Cl | H | CH2N(tBu)CO2Et | CF3 |
| 112 | CF3 | H | Br | H | H | CF3 |
| 120 | CF3 | H | Br | H | CH2N(C6H11)-CO2Et | CF3 |
可以优选提到的可用于根据本发明的混合物中的抑球虫剂和聚醚抗菌素是：氨丙嘧吡啶，在某些情况下要与叶酸拮抗剂组合使用双氯苄氨胍托三嗪莫能菌素沙利霉素马度米星
根据本发明的混合物对温血动物的毒性低，可用于防治在家畜管理和家畜饲养中有用的、饲养的、动物园的、实验室的、试验和宠物动物上出现的寄生性原生动物。此外，本发明的混合物对害虫发育的所有或各个阶段都有活性，对抗性品系及正常敏感品系具有活性。防治寄生性原生动物的目的是为了减轻疾病，降低死亡和工作中的耗损(产肉、产奶、产毛、产皮、产蛋、产蜜等)，因此本发明活性化合物的使用使得更经济和更简单的家畜管理成为可能。寄生性原生动物包括：鞭毛总纲(鞭毛虫纲)，例如，锥体虫科，例如布氏锥虫、冈比亚锥虫、罗得西亚锥虫、刚果锥虫、枯氏锥虫、伊氏锥虫、马媾疫锥虫、路氏锥虫、T.percae、狗锥虫、活泼锥虫、巴西利什曼虫、杜氏利什曼虫、热带利什曼虫，例如，毛滴虫科，例如兰伯氏贾第虫、狗贾第虫。肉足鞭毛亚门(根足虫纲)，例如内变形虫科，例如痢疾阿米巴，哈特曼氏变形虫科，例如棘变形虫属、哈氏虫属。Apicomplexa(孢子虫纲)如艾美球虫科，例如，Eimeria acervulina、E.adenoides、E.alabahmensis、E.anatis、E.anseris、E.arloingi、E.ashsta、E.auburnensis、牛艾美虫球虫、E.brunetii、狗艾美球虫、E.chinchillae、鱼艾美球虫、哥伦比亚艾美球虫、E.contorta、E.crandalis、E.debliecki、E.dispersa、E.ellipsoidales、镰形艾美球虫、E.faurei、E.flarescens、E.gallopavonis、E.hagani、E.intestinalis、E.iroquoina、E.irresidua、E.iabbeana、E.leucarti、E.magna、E.maxima、E.media、E.meleagridis、E.meleagrimitis、E.mitis、E.necatrix、E.ninakohlyakimovae、绵羊艾美球虫、E.parva、穿孔艾美氏球虫、E.phasani、E.piriformis、E.praecox、E.residua、E.scabra、E.Spec.、E.stiedai、猪艾美球虫、禽艾美球虫、E.truttae、祖尔尼氏艾美球虫，球虫属、大等孢球虫、犬等孢球虫、猫等孢球虫、Isospora. ohioensis、I.rivolta、等孢球虫(I.spec.)、猪等孢球虫、Cystisospora spec.、Cryptosporidiumspec.，例如，弓形体科，例如鼠弓形体，例如，肉孢子虫科，例如牛-犬肉孢子虫、牛-人肉孢子虫、羊-犬肉孢子虫、牛-猫肉孢子虫、肉孢子虫(S.spec.)、猪-人肉孢子虫，例如Leucozoidea，例如Leucozytozoonsimondi，例如疟原虫科，例如Plasmodium berghei、恶性疟原虫、三日疟原虫、卵囊形疟原虫、间日疟原虫、疟原虫(P.spec)、例如梨浆虫属，例如阿根廷梨浆虫、牛梨浆虫、犬梨浆虫、梨浆虫(B.spec.)、Theileria parva、泰来虫(Theileria spec.)，例如隐球虫亚目，例如犬肝簇虫、肝簇虫(Hepatozoon spec.)。
有用和饲养的家畜包括哺乳动物诸如牛、马、绵羊、猪、山羊、骆驼、水牛、驴、兔、黄占鹿、驯鹿，皮毛饲养动物诸如水貂、灰鼠、浣熊，鸟类诸如鸡、火鸡、鸭、鸽子，家养或动物园的鸟类。
实验和试验用动物包括大鼠、小鼠、豚鼠、金色仓鼠、狗和猫等。
宠物包括狗和猫。
可用作预防和治疗两者的应用。
活性化合物可以直接使用或经肠道、非肠道、皮肤或鼻以适当的制剂形式使用。
活性化合物的肠道使用方式可以是：以粉剂、栓剂、片剂、胶囊、糊剂、饮剂、粒剂、顿服剂、大丸剂、混药喂食或饮用水等形式口服。皮肤使用方式可以是：以点滴、喷雾、沐浴、冲洗、浇泼或涂药斑，撒药粉。非肠道使用方式可以是：以(肌肉，皮下，静脉，腹膜)形式注射或输液。
合适的制剂是：
如注射液、口服液、稀释后可口服的浓缩液等形式的溶液，用于皮肤或体腔的溶液、浇泼制剂、凝胶；
用于口服或皮肤和用于注射的乳状液和悬浮液，半固体制剂；
活性化合物掺入软膏基剂或水包油或油包水乳状液基剂的制剂；
如粉剂，预混物或浓缩物、粒剂、丸剂、片剂、大丸剂、胶囊剂、气雾剂和吸入剂，含有活性组份的成形粒剂等固体制剂。
用于静脉、肌肉和皮下注射的注射液。
注射液制备是把活性化合物溶于适当的溶剂和可行的助剂(如增稠剂、酸、碱、缓冲盐溶液、抗氧化剂、防腐剂)。溶液通过过滤消毒并装瓶。
可以提到的溶剂是生理可忍受的溶液，如水、醇(如乙醇、丁醇、苄醇、甘油、烃、丙烯乙二醇、聚乙烯乙二醇、N-甲基吡咯烷酮)及其混合物。
如果适宜，活性化合物也以溶解于生理可忍耐的适合于注射的植物油或合成油。
可以提到的增溶剂是：能够提高活性组份在主要溶剂中溶解性，或阻止活性组份沉淀的溶剂，其实例有聚乙烯吡咯烷酮、聚乙氧基化的蓖麻油、聚乙氧基化的脱水山梨醇酯。
防腐剂包括：苄醇、三氯丁醇、对羟基苯甲酸酯、正丁醇。
口服液直接使用。浓缩液在预先稀释到使用浓度后口服。口服液和浓缩液按照前边叙述的制备注射液的方法制备，也可能在无菌操作下进行分装处理。
用于皮肤的溶液可以以施药斑、涂药、擦药、喷雾或喷射、或用于点滴、沐浴或淋洗等形式使用。这些溶液按照上述的制备注射液的方法制备。
制备过程中加入增稠剂可能是有利的。增稠剂是无机增稠剂(如膨润土、胶态二氧化硅、单硬脂酸铝)和有机增稠剂(如纤维素衍生物，聚乙烯醇及其共聚体，丙烯酸酯及甲基丙烯酸酯)。
凝胶被推荐用于或涂沫在体腔上或里部，凝胶制备通过向溶液中增加足够的增稠剂，溶剂可以按照注射液的方法制备，从而形成具有软膏粘度的一种透明组合物。使用的增稠剂是上文提到的增稠剂。
浇泼制剂倒到或喷雾到皮肤的限定区域，在这种情况下，活性化合物或是通过皮肤和系统作用渗透或是在身体的表面分散。
浇泼制剂是通过溶解、悬浮和乳化活性成分于合适的皮肤可适应的溶剂或溶剂混合物中来制备。如可行的话，也可以加入其它助剂(如着色剂、吸收促进物、抗氧化物、防晒剂、粘结剂)。
可以提到的溶剂是：水、链烷醇、乙二醇、聚乙二醇、聚丙二醇、甘油、芳族醇(如苯甲醇、苯乙醇、苯氧基乙醇)、酯(如乙酸乙酯、乙酸丁酯、苯甲酸苄基酯)、醚(如亚烷基二醇烷基醚、二丙二醇单甲基醚、二甘醇单丁基醚)、酮(如丙酮、甲乙酮)、芳香族和/或脂肪族烃、植物油或合成油、DMF、二甲基乙酰胺、N-甲基吡咯烷酮、2-二甲基-4-氧基亚甲基-1，3-二氧戊环。
着色剂是所有允许用于家畜且能够溶解或悬浮的着色剂。
吸收促进物是例如二甲基亚砜、扩散油(如十四烷酸异丙基酯、二丙二醇壬酸酯、硅氧烷油、脂肪酸酯、甘油三酯、脂肪醇)。
抗氧化剂是亚硫酸盐或偏亚硫酸氢盐如偏亚硫酸氢钾、抗坏血酸、丁基化的羟甲苯、丁基化的羟基苯甲醚、维生素E。
防晒剂是例如包括二苯甲酮或苯基苯并咪唑磺酸(novantisolicacid)等系列的衍生物。
粘结剂是例如纤维素衍生物、淀粉衍生物、聚丙烯酸酯、天然聚合物(如藻酸盐、明胶)。
乳液可用于口服、皮肤或作为注射剂液。
乳液可以是油包水型或水包油型。
它们可按照以下方法制备：通过把活性化合物溶于疏水相或亲水相，并将后者借助于乳化剂和(如合适的话)其它辅助剂(如着色剂、吸收促进剂、防腐剂、抗氧化物、防晒剂、增稠剂辅助)，与另一相的溶剂均化。
下面是可以提到的疏水相(油)：石蜡油、硅氧烷油、天然植物油(如芝麻油、杏仁油、蓖麻油)、合成甘油三酯如辛酸/癸酸甘油二酯、带有链长C8-12的植物脂肪酸或其它特别选用的天然脂肪酸的甘油三酯混合物、饱和或不饱和的，也可含羟基的脂胶酸的部分甘油酯混合物，C8/C10脂肪酸的单或双甘油酯。
脂肪酸酯(如硬脂酸乙酯、己二酸二正丁酯、月桂酸己基酯、壬基酸二丙二醇酯、中等链长的支链脂肪酸与链长C16-C18的饱和脂肪醇的酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、链长C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙酯、油酸油酯、油酸癸酯、油酸乙酯、乳酸乙酯，蜡质脂肪酸酯如邻苯二甲酸二丁基酯及己二酸二异丙基酯，涉及后者的酯混合物包括诸如异十三烷基醇、2-辛基十二烷醇、十六烷基硬脂基醇、油醇等。
脂肪酸包括油酸及其混合物。
下面是可以提到的亲水相：水、醇(如丙二醇、甘油、山梨醇及其混合物)。
可以提到的乳化剂包括：非离子型表面活性剂，例如聚乙氧基化的蓖麻油、聚乙氧基化的脱水山梨醇单油酸酯、脱水山梨醇单硬酯酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基苯酚聚乙二醇醚。
两性表面活性剂如N-月桂基-β-亚氨基二丙酸二钠盐或卵囊磷酯；
阴离子型表面活性剂，如月桂基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚乙二醇醚正磷酸酯单乙醇胺盐；阳离子型表面活性剂如十六烷基三甲基氯化铵。
可以提到的其他的辅助剂是：
增粘和乳液稳定物质：如羧甲基纤维素、甲基纤维素及其它纤维素和淀粉衍生物、聚丙烯酸酯、藻酸盐、动物胶、阿拉伯树胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯醚与顺式丁烯二酐的共聚物、聚乙二醇、蜂蜡、胶态硅石或提到的物质的混合物。
悬浮液可以经口、经皮或作为注射液使用。悬浮液可通过在液体赋形剂中悬浮活性物质来制备，在合适情况下可添加其它辅助剂(如润湿剂、着色剂、吸收促进剂、防腐剂、抗氧化剂、防晒剂)。
可以提到的液体赋形物是所有的均质溶剂及其混合物。
可以提到的润湿剂(分散剂)是上文指明的表面活性剂。
可以提到的其他辅助剂是上文提到的那些。半固体制剂可以经口或经皮肤给药。它们不同于上文提及的悬浮液和乳液仅在于它们有更高的粘度。
要制备固体制剂，活性组合物要与合适的赋形剂混合，在合适情况下可加入辅助剂，并转化成要求的形状。
可以提到的赋形剂是所有生理可忍受的固体惰性物质。无机和有机物质都可被采用。无机物质是如氯化钠、碳酸盐(如碳酸钙)、碳酸氢盐、氧化铝、硅石、矾土、沉淀的或胶状的二氧化硅。
有机物质是例如糖、纤维素、粮食和饲料(如奶粉、动物粉、谷物粉和粗粉、淀粉)。
辅助剂是上文已经列出的防腐剂、抗氧化剂、着色剂。
其它合适的辅助剂是润滑剂和glidants，例如硬脂酸镁、硬脂酸、滑石、膨润土，崩解促进剂如淀粉或交联聚乙烯吡咯烷酮，粘合剂例如淀粉、明胶或直链聚乙烯吡咯烷酮，和干粘合剂如微晶纤维素。
活性化合物也可存在于与增效剂或其它活性物混合的制剂中。
直接可用的制剂包含浓度为10ppm到按重量计20％的活性化合物，优选按重量计0.1到10％。
式(I)的苯并咪唑类化合物在此情况下与合成的抑球虫剂或聚醚抗菌素的重量比为1∶0.1-10，优选1∶1-10。
使用前稀释的制剂含有活性化合物的浓度按重量计0.5-90％，优选按重量计1-50％。
业已证实，通常每天每公斤体重施用大约0.5-50mg活性化合物，优选1-20mg对达到有效的结果会是有利的。
活性化合物也可以通过饲料或饮用水给药于家畜。
饲料和食料含有与适合的可食物组合的0.01-250ppm，优选0.5-100ppm的活性化合物。
可以使用这样的饲料和食料来达到治疗和预防的二种目的。
这种饲料和食料可以通过将一种浓缩物或预混物与常用饲料混合来制备，其中浓缩物或预混物含有与可食用的有机或无机载体混合的按重量计0.5-30％，优选按重量计1-20％的活性物质。食用载体包括如花生粉或花生和大豆粉或矿物盐，优选含有少量的食用粉尘抑制油如谷物油或豆油。在喂家畜以前，这种方法获得的预混物能够添加到完整的粮食中。
抑球虫剂的使用可以通过举例的方式提及：例如，为了治疗和预防家禽(尤其是鸡、鸭、鹅或火鸡)的球虫病，将0.1-100ppm，优选0.5-100ppm的活性化合物与合适的食用物质(如一种营养丰富的饲料)混合。如果需要，这些量均可增加，尤其如果服药对象对活性化合物有很好的耐药力。通过饮用水给药可以相应地处理。
处理单个动物，例如处理哺乳动物的球虫病或弓浆虫病时，为达到所需要的结果，优选以活性化合物0.5-100mg/kg的量给药。然而，尤其是作为试验动物的体重或给药方法的性质的函数，也因为动物种类和个体对活性化合物或剂型种类的反应和取食的时间或间隔期不同，有时也有偏离指定的用量的必要，因此，在特定情况下使用量少于前面提到的最低用量就够了，而其它情况下就必须超过规定的最高用量。当大量的给药时，也许在一天中分几次给药是有利的。
根据本发明，混合物的药效可通过如下设计的笼式试验来确证，其中家畜用特殊的单个成分处理和用单个成分组合成的组合物处理。小鸡球虫病的笼式试验
无球虫感染的饲养8-12天的雄性雏鸡(例如LSTBrinkschulte/Senden)，从感染前(＝a.i.)3天(day-3)到感染后(＝p.i.)8(9)天，接受以ppm给出的所述浓度的本发明化合物(试验物质)。每笼中养三只小鸡。每个剂量处理一个或多个组。通过用试管直接在谷物中加入大约50,000个Eimeria acervalina的孢子卵囊细胞和每个组大约20,000个E.maxima和禽艾美球虫(E.tenella)卵囊细胞进行感染。所用的均是高毒品系。确切的感染剂量要调整合适，当可能时，使三分之一未处理的试验感染的雏鸡死于感染，为了评价药效可采用下列标准：增加从试验开始到试验结束的谷物，从感染后算起的致死率，第5天和第7天p.i.的排泻物和血液分泌的宏观估计(等级0-6)和肠粘液的宏观估计，尤其是盲肠粘液(0-6级)和卵囊细胞的排泻，以及24小时内卵囊细胞形成孢子的比例(％表示)。排泻物中的卵囊细胞数用一个McMaster计数分隔法测量(见Engelbrech和合作者的“Parasitologische Arbeitsmethodenin Medizin and Veterin rmedizin，Akademie-Verloay，Berlin(1965))。个体调整结果涉及未处理的未感染对照组，并计算总的等级(参见，A.Haberkorn(1986)，第263至270页，Research in Avian Coccidiosis，L.R，McDougald，L.P.Joyner，P.L.Long编辑，Proceedings of theGeorgia Coccidiosis Conference 1985年11月18-20日，Athens/Georgia USA)。
含有活性化合物的饲料以这样的方式进行制备：所需量的活性化合物与能给予动物均衡的营养的饲料(例如与下文指明的小鸡饲料)彻底混合。
如果意欲制备浓缩剂或预混物并最终稀释到饲料中至在试验中提到的数据，通常按重量计约1至30％，优选约10至20％活性化合物与含有少量食用抗粉尘油(如谷物油或大豆油)的可食有机或无机载体(如玉米和豆粉或矿物盐)混合。在给药以前，通过这种方式得到的预混物被添加到完整的家畜饲料中。
根据本发明，用于家禽饲料的一个适当组合物例子如下：
52.00％粗谷物饲料粉，尤其是：40％玉米，12％小麦
17.00％提取的粗豆粉
5.00％玉米皮
3.00％鱼粉
3.00％矿物质混合物
3.00％苜蓿粉
2.50％维生素预混物
2.00％碾碎的小麦胚芽
2.00％豆油
2.00％肉和骨粉
1.50％乳清粉
1.00％糖蜜
1.00％结合到啤酒糟上的啤酒酵母，
100.00％这样的饲料含有18％粗蛋白、5％粗纤维、1％Ca、0.7％P，和每公斤含1,200I.U.维生素A、1,200I.U.维生素D3、10mg维生素E和20mg杆菌肽锌。
本发明组合的试验结果通过列举的方式列于下列表格中。与单个成分相比，组合的增效活性从卵囊母细胞排泄，以及尸体解剖、体重增加和更强的耐药力方面来看效果特别明显。
下面的表中，“处理”项缩写词代表：n.inf.contr. ＝未被感染的对照组inf.contr. ＝感染的对照组amprol comb. ＝氨丙嘧吡啶与磺胺喹恶啉和4-乙酰氨基-2-乙氧基苯甲
酸甲酯的组合物1 ＝苯并咪唑药物举例代号
在“ppm”项中，饲料中使用的活性化合物浓度以ppm表示。
在“死亡率”项中，死亡禽的百分率用％表示，并且试验中死亡/禽的禽数用n表示。
在“未被感染的对照组的重量％”项中，处理的鸟的重量与未被感染的对照组的比率被列出。
在“减退级别”，“伤害级别”和“卵囊对照组％”单个处理受到影响的数据给出。
在“药效”项中，所有的结果分级：0％表示无效，100％表示全部有效。表1用Eimeria acervalra，E.maxima和禽艾美球虫感染试鸡
*＝x 1000表2
*＝x 1000#＝由于毒性表3
*＝x 1000#＝由于毒性表4
*＝x 1000#＝由于中毒表5
*＝x 1000#＝由于中毒表6
*＝x 1000表7
*＝x 1000表8
*＝x 1000#＝由于毒性表9
*＝x 1000
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 50 | 3/6 | 46 | 6 | 6 | 100915* | 10055* | 1001520* | 1002490* | 0 |
| amprol.comb. | 50 | 0 | 0/3 | 71 | 0.7 | 63 | 36 | 46 | 52 | 36 | |
| 75 | 0 | 0/3 | 75 | 0 | 100 | 36 | 100 | 78 | 42 | ||
| 1 | 5 | 0 | 0/3 | 80 | 4-6 | 4 | 15 | 100 | 14 | 43 | 39 |
| amprolcomb.+1 | 50+5 | 0 | 0/3 | 89 | 0 | 0 | 1.5 | 2 | 1 | 1.5 | 82 |
| 75+5 | 0 | 0/3 | 95 | 0 | 0.7 | 0.26 | 0 | 0.32 | 0.29 | 98 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 0 | 0/6 | 61 | 6 | 1003810* | 100480* | 1002980* | 1007270* | 0 | |
| 莫能菌素 | 25 | 0 | 0/3 | 44 | 6 | 44 | 100 | 100 | 81 | 7 | |
| 50 | 0 | 0/3 | 88 | 6 | 13 | 33 | 19 | 22 | 43 | ||
| 1 | 2.5 | 33 | 1/3 | 83 | 6 | 6 | 14 | 38 | 41 | 31 | 35 |
| 5 | 0 | 0/3 | 76 | 6 | 5.7 | 06 | 3 | 3 | 2.1 | 69 | |
| 10 | 33 | 1/3# | 100 | 0-2 | 3.5 | 0 | 0 | 0 | 0 | 92 | |
| 莫能菌素1 | 252.55 | 0 | 0/3 | 66 | 6 | 6 | 13 | 29 | 24 | 22 | 32 |
| 25+5 | 0 | 0/3 | 102 | 0-2 | 4.3 | ＜0.1 | ＜0.1 | 0.1 | 0.1 | 92 | |
| 25+10 | 0 | 0/3 | 102 | 0-2 | 0.7 | 0 | 0 | ＜0.1 | ＜0.1 | 98 | |
| 50+2.5 | 0 | 0/3 | 97 | 1 | 0.3 | ＜0.1 | 0.1 | ＜0.1 | ＜0.1 | 96 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 83 | 5/6 | 64 | 6 | 6 | 1001420* | 100220* | 1003560* | 1005200* | 0 |
| 双氯苄氨胍 | 16.5 | 0 | 0/3 | 95 | 1 | 5 | 38 | 9 | 23 | 23 | 60 |
| 1 | 5 | 67 | 2/3 | 87 | 6 | 6 | 11 | 15 | 11 | 12 | 40 |
| 10 | 33 | 1/3# | 83 | 6 | 6 | 0.8 | 0.9 | 0.6 | 0.8 | 71 | |
| 双氯苄氨胍1 | 16.5+5 | 0 | 0/3 | 114 | 0 | 13 | 1.2 | 4 | 2 | 9 | 88 |
| 16.5+10 | 33 | 1/3# | 96 | 0 | 4 | 0.01 | 0 | 0 | ＜0.01 | 94 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 83 | 5/6 | 64 | 6 | 6 | 1001430* | 100220* | 1003560* | 1005200* | 0 |
| toltra-zuril | 10 | 0 | 0/3 | 84 | 3 | 6 | 3 | 4 | 1 | 3 | 68 |
| 15 | 0 | 0/3 | 106 | 5 | 3.3 | 0.6 | 0 | 0.4 | 0.3 | 88 | |
| 1 | 5 | 67 | 2/3 | 87 | 6 | 6 | 11 | 15 | 11 | 12 | 40 |
| 10 | 33 | 1/3# | 83 | 6 | 6 | 0.8 | 0.9 | 0.6 | 0.8 | 71 | |
| toltra-zuril+1 | 10+5 | 0 | 0/3 | 76 | 6 | 6 | 0.7 | 2 | 0.6 | 1.1 | 72 |
| 15+10 | 0 | 0/3 | 94 | 0 | 4.3 | 0 | 0 | 0 | 0 | 98 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率tot. | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 0 | 0.6 | 62 | 6 | 6 | 1001260* | 100150* | 1001640* | 1003050* | 0 |
| 莫能菌素 | 25 | 0 | 0/3 | 72 | 4 | 5.3 | 86 | ＞100 | ＞100 | 95 | 0 |
| 50 | 0 | 0/3 | 78 | 6 | 6 | 35 | 93 | 38 | 55 | 30 | |
| 100 | 0 | 0/3 | 92 | 0 | 2.7 | 11 | 7 | 20 | 13 | 69 | |
| 74 | 5 | 0 | 0/3 | 59 | 6 | 6 | ＞100 | 40 | ＞100 | 80 | 4.3 |
| 10 | 33 | 1/3# | 80 | 0 | 4.5 | 0.7 | 3 | 2 | 1.9 | 75 | |
| 莫能菌素+74 | 25+5 | 0 | 0/3 | 83 | 0 | 5.3 | 8 | 9 | 15 | 11 | 58 |
| 25+10 | 0 | 0/3 | 80 | 4 | 4.3 | 1 | 0 | 0.9 | 0.6 | 69 | |
| 50+5 | 0 | 0/3 | 90 | 0 | 2.3 | 0.08 | 0 | 0.13 | 0.07 | 98 | |
| 50+10 | 33 | 1/3# | 98 | 0 | 0.5 | 0.7 | 0 | 0.05 | 0.25 | 100 | |
| 100+5 | 0 | 0/3 | 89 | 0 | 1.3 | 1 | 0.7 | 4 | 1.9 | 85 | |
| 100+5 | 0 | 0/3 | 87 | 0 | 0.7 | 0 | 0 | 0.02 | 0.01 | 87 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf. contr. | 0 | 0 | 0/6 | 59 | 6 | 6 | 1002760* | 100200* | 1001820* | 1004780* | 0 |
| 溴氯哌喹酮 | 1 | 0 | 0/3 | 67 | 2 | 2 | 50 | 50 | 96 | 66 | 26 |
| 3 | 0 | 0/3 | 72 | 0 | 0.7 | 5 | 4 | 19 | 9 | 70 | |
| 74 | 5 | 0 | 0/3 | 38 | 6 | 6 | 84 | 100 | 45 | 76 | 4 |
| 10 | 33 | 1/3 | 48 | 6 | 6 | 100 | 44 | 44 | 63 | 7 | |
| 溴氯-哌喹酮74 | 1+10 | 0 | 0/3 | 55 | 0 | 0.7 | 2.5 | 6 | 13 | 7.2 | 53 |
| 3+5 | 0 | 0/3 | 76 | 0 | 0 | 3 | 0 | 5 | 2.7 | 85 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 33 | 2/6 | 62 | 6 | 6 | 100645* | 100115* | 100865* | 1001625* | 0 |
| 盐霉素 | 15 | 0 | 0/3 | 85 | 6 | 6 | 81 | 87 | 58 | 75 | 16 |
| 30 | 0 | 0/3 | 100 | 3-5 | 2.3 | 9 | 0 | 22 | 10 | 74 | |
| 40 | 0 | 0/3 | 112 | 0 | 0 | 2.5 | 5 | 1.7 | 3 | 90 | |
| 60 | 10 | 0 | 0/3 | 65 | 6 | 6 | 59 | 70 | 53 | 61 | 5 |
| 12.5 | 0 | 0/3 | 86 | 6 | 6 | 71 | 100 | 65 | 79 | 16 | |
| 15 | 0 | 0/3 | 85 | 6 | 6 | 62 | 100 | 72 | 78 | 16 | |
| 20 | 0 | 0/3 | 84 | 4-6 | 2.3 | 31 | 87 | 40 | 53 | 32 | |
| 盐霉素+.60 | 15+10 | 0 | 0/3 | 100 | 6 | 2.3 | 28 | 70 | 53 | 50 | 37 |
| 15+12.5 | 0 | 0/3 | 100 | 0 | 0.3 | 0.09 | 0.5 | 0.2 | 0.27 | 100 | |
| 30+10 | 0 | 0/3 | 98 | 0 | 0.3 | 0 | 0 | 0 | 0 | 100 | |
| 30+12.5 | 0 | 0/3 | 96 | 0 | 0 | 0 | 0.2 | 0 | 0.07 | 100 | |
| 30+15 | 0 | 0/3 | 103 | 1 | 1 | 0 | 0 | 0 | 0 | 96 | |
| 30+20 | 0 | 0/3 | 101 | 0 | 0.7 | 0 | 0 | 0 | 0 | 98 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率tot. | ||||
| 40+10 | 0 | 0/3 | 100 | 0 | 0 | 0.03 | 0 | 0.1 | 0.03 | 100 | |
| 40+12.5 | 0 | 0/3 | 94 | 2 | 0.7 | 0 | 0 | 0 | 0 | 95 | |
| 40+20 | 0 | 0/3 | 97 | 0 | 0 | 0 | 0 | 0 | 0 | 100 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 17 | 1/6 | 61 | 6 | 6 | 1001080* | 100220* | 1002550* | 1003850* | 0 |
| toltrazuril | 2.5 | 0 | 0/3 | 59 | 6 | 5.3 | 12 | 9 | 11 | 11 | 25 |
| 59 | 5 | 0 | 0/3 | 61 | 6 | 6 | 91 | 100 | 99 | 100 | 0 |
| 25 | 33 | 1/3# | 84 | 1 | 5 | 0 | 0 | 0.2 | 0.1 | 79 | |
| 59+toltra.zuril | 2.5+5 | 0 | 0/3 | 69 | 6 | 5.7 | 11 | 9 | 12 | 11 | 35 |
| 2.5+25 | 0 | 0/3 | 92 | 0 | 2 | 0 | 0 | 0 | 0 | 100 | |
| 处理 | ppm | 死亡率 | 未被感染对照组的重量％ | 减退级别 | 伤害级别 | 感染对照组中的卵囊％ | ％总效率 | ||||
| ％ | n | ac. | max. | ten. | tot. | ||||||
| n.inf.contr. | 0 | 0 | 0/6 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 100 |
| inf.contr. | 0 | 0 | 0/6 | 54 | 6 | 6 | 1001570* | 10070* | 1001057* | 1002697* | 0 |
| 溴氯哌喹酮 | 1 | 33 | 1/3 | 81 | 4-6 | 6 | 41 | 100 | 49 | 63 | 24 |
| 0 | 0/3 | 87 | 0 | 0 | ＜0.1 | 0 | ＜0.1 | ＜0.1 | 91 | ||
| 112 | 1 | 0 | 0/3 | 41 | 6 | 6 | 100 | 57 | 91 | 83 | 0 |
| 5 | 0 | 0/3 | 88 | 0-2 | 6 | 0.8 | 10 | 2.4 | 4.4 | 77 | |
| 溴氯哌喹酮112 | 1+1 | 33 | 1/3 | 88 | 6 | 6 | 12 | 100 | 17 | 43 | 30 |
| 3+1 | 0 | 0/3 | 102 | 0 | 0 | 1 | 0 | 0.7 | 0.6 | 96 | |
| 3-5 | 0 | 0/3 | 83 | 0 | 1.7 | ＜0.1 | 0.6 | 0.2 | 0.1 | 89 | |
Claims (3)
1.式(I)的取代的苯并咪唑类化合物与一种或多种后面提到的化合物的混合物，
其中R1，R2，R3和R4彼此独立地各自代表氢，卤素，代表各任选取代的烷基，烷氧基，烷硫基，烷基亚磺酰基，烷基磺酰基，代表各任选取代的稠合上的二氧亚烷基，但是其中取代基R1，R2，R3和R4中至少有一个不是氢和卤素，R5代表氢，代表烷基，该烷基可以由以下相同或不同的基团取代一次或多次：OH，CN，NH2，烷基，环烷基，链烯基，炔基，烷氧基，卤代烷氧基，烷硫基，卤代烷硫基，链烯氧基，炔氧基，氨基羰基，任选取代的烷基羰基，任选取代的(杂-)芳基羰基，任选取代的烷氧羰基(AlkO-CO-)，任选取代的烷氧基羰基氧基(AlkO-COO-)，氨基磺酰基(SO2NH2)，任选取代的单或二烷基氨基磺酰基，酰化氨基(AlkCON(R7)-或AlkOCON(R7)-)，其中R7等同于氢，烷基或环烷基，或任选取代的烷基磺酰基氨基(烷基-SO2NH-)，或烷基磺酰基-N-烷基氨基(烷基-SO2-N-烷基)，任选取代的芳基磺酰基氨基(芳基-SO2NH-)或芳基磺酰基-N-烷基氨基(芳基-SO2-NAlk-)，任选取代的二烷基氨基，此外，R5代表任选取代的烷氧基羰基，任选取代的(杂-)芳氧基羰基，烷基磺酰基，烯基磺酰基，(杂-)芳基磺酰基，或-SO2NR8R9，-CONR8R9-或-P(O)(NR8R9)2，其中R8和R9代表H或任选由一或多个基团取代的烷基，R6代表氟代烷基，上面所述的一或多个化合物为：聚醚类抗菌素(如马度米星，拉沙洛西，莫能菌素，甲基盐霉素，沙利霉素)或合成的抑球虫剂如：氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶鎓氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶+磺胺喹鎓+磺胺喹喔啉 喔啉氯化1(-(4-氨基-2-正丙基-5-嘧啶基甲基)-2-甲基吡啶 氨丙嘧吡啶+磺胺喹鎓+磺胺喹喔啉+4-乙酰氨基-2-乙氧基苯甲酸甲酯 喔啉+4-乙酰氨基-2-
乙氧基苯甲酸甲酯4，4-二硝基对称二苯脲+2-羟基-4，6-二甲基嘧啶 二硝基苯脲3，5-二氯-2，6-二甲基-4-吡啶醇 二氯二甲吡啶酚3，5-二氯-2，6-二甲基-4-吡啶醇+7-苄氧基-6-丁基-1，4- 二氯二甲吡啶酚+苄二氢-4-氧喹啉-3-羧酸甲酯 氧喹甲酯6-正癸氧基-7-乙氧基-4-羟基喹啉-3-羧酸乙酯 癸氧喹酯9-(2-氯-6-氟苯基甲基)-9H-嘌呤-6-胺 阿谱西特(±)-2，6-二氯-α-(4-氯苯基)-4-(4，5-二氢-3，5-二氧代- 苯乙腈，地克珠利1，2，4-三嗪-2(3H)-基)-苯乙腈1-[3-甲基-4-(4’-三氟甲基硫基苯氧基)-苯基]-3-甲基- 托三嗪1，3，5-三嗪-2，4，6(1H，3H，5H)-三酮4，4-二硝基对称二苯脲+2-羟基-4，6-二甲基嘧啶 双氯苄氨胍
[＝nicarbazin]7-溴-6-氯-常山碱 卤夫酮3，5-二硝基-O-甲苯甲酰胺 二硝甲苯酰胺作为家畜上防治寄生性原生动物，特别是球虫的组合物。
2.权利要求1的式(I)苯并咪唑类化合物与聚醚抗菌素和合成的抑球虫剂的混合物用于制备防治家畜的寄生性原生动物的组合物的应用。
3.权利要求1的混合物用于防治家畜中寄生性原生动物的应用。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19519821A DE19519821A1 (de) | 1995-05-31 | 1995-05-31 | Mittel gegen parasitäre Protozoen |
| DE19519821.2 | 1995-05-31 |
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| CN115768426A (zh) * | 2020-07-03 | 2023-03-07 | 日本农药株式会社 | 球虫病防治剂和球虫病防治剂的使用方法 |
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| US6562829B1 (en) * | 1997-05-23 | 2003-05-13 | Hadasit Medical Research Services & Development Co., Ltd. | Treatment of hepatic cirrhosis |
| DE19824483A1 (de) * | 1998-06-02 | 1999-12-09 | Bayer Ag | Halbfeste wäßrige Zubereitungen für orale Applikation von Toltrazuril-Sulfon |
| DE19831985A1 (de) * | 1998-07-16 | 2000-01-20 | Bayer Ag | Substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| EP1119255A4 (en) | 1998-10-08 | 2009-04-15 | New Ace Res Company | NEW COMPOSITIONS AND METHOD FOR THE PREVENTION AND TREATMENT OF PROTOCOL DISEASES |
| DE19958388A1 (de) * | 1999-12-03 | 2001-06-07 | Bayer Ag | Triazinonverbindungen zur Behandlung von durch den Befall mit parasitischen Protozoen bedingten Krankheiten |
| DE10049468A1 (de) * | 2000-10-06 | 2002-04-11 | Bayer Ag | N-Alkoxyalkyl-substituierte Benzimidazole, ihre Herstellung und ihre Verwendung als Mittel gegen parasitäre Protozoen |
| US20030179058A1 (en) * | 2002-01-18 | 2003-09-25 | Microlab, Inc. | System and method for routing input signals using single pole single throw and single pole double throw latching micro-magnetic switches |
| DE102004042958A1 (de) * | 2004-09-02 | 2006-03-09 | Bayer Healthcare Ag | Neue antiparasitäre Kombination von Wirkstoffen |
| DE102005000746A1 (de) * | 2005-01-05 | 2006-07-13 | Bayer Healthcare Ag | Bekämpfung der Histomoniasis |
| DE102007025908A1 (de) | 2007-06-01 | 2008-12-04 | Bayer Healthcare Ag | Formulierungen enthaltend Triazinone und Eisen |
| DE102009038950A1 (de) | 2009-08-26 | 2011-03-03 | Bayer Animal Health Gmbh | Neue antiparasitäre Kombination von Wirkstoffen |
| JP7069119B2 (ja) | 2016-08-11 | 2022-05-17 | アダミス ファーマシューティカルズ コーポレーション | 医薬組成物 |
| US11564910B2 (en) | 2017-12-08 | 2023-01-31 | Adamis Pharmaceuticals Corporation | Drug compositions |
| WO2020093014A1 (en) * | 2018-11-02 | 2020-05-07 | Adamis Pharmaceuticals Corporation | Drug compositions |
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| DE4237617A1 (de) * | 1992-11-06 | 1994-05-11 | Bayer Ag | Verwendung von substituierten Benzimidazolen |
| US5331003A (en) * | 1993-03-26 | 1994-07-19 | Eli Lilly And Company | Anticoccidial methods |
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| CN115768426A (zh) * | 2020-07-03 | 2023-03-07 | 日本农药株式会社 | 球虫病防治剂和球虫病防治剂的使用方法 |
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| Publication number | Publication date |
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| SK159897A3 (en) | 1998-09-09 |
| KR100424610B1 (ko) | 2004-07-27 |
| HUP9802292A3 (en) | 2001-04-28 |
| MX9709187A (es) | 1998-03-31 |
| AR003421A1 (es) | 1998-08-05 |
| PL185216B1 (pl) | 2003-04-30 |
| AU694663B2 (en) | 1998-07-23 |
| TW403651B (en) | 2000-09-01 |
| CZ290157B6 (cs) | 2002-06-12 |
| AU5819396A (en) | 1996-12-18 |
| NO975433D0 (no) | 1997-11-26 |
| DE19519821A1 (de) | 1996-12-05 |
| EP0828487A1 (de) | 1998-03-18 |
| BR9608594A (pt) | 1999-01-05 |
| DK0828487T3 (da) | 2004-04-05 |
| WO1996038140A1 (de) | 1996-12-05 |
| NO320712B1 (no) | 2006-01-23 |
| EP0828487B1 (de) | 2003-11-26 |
| CZ378997A3 (cs) | 1998-03-18 |
| SK284508B6 (sk) | 2005-05-05 |
| DE59610836D1 (de) | 2004-01-08 |
| CN1196485C (zh) | 2005-04-13 |
| NZ308526A (en) | 1999-05-28 |
| US6034116A (en) | 2000-03-07 |
| HUP9802292A2 (hu) | 1999-05-28 |
| KR19990022045A (ko) | 1999-03-25 |
| BR9608594B1 (pt) | 2010-07-27 |
| ES2211962T3 (es) | 2004-07-16 |
| JPH11505854A (ja) | 1999-05-25 |
| PL323594A1 (en) | 1998-04-14 |
| NO975433L (no) | 1998-01-20 |
| ZA964415B (en) | 1997-01-09 |
| ATE254917T1 (de) | 2003-12-15 |
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