CN1100537C - 用作杀体内寄生虫剂的昆虫烟碱能乙酰胆碱受体兴奋剂或拮抗剂 - Google Patents
用作杀体内寄生虫剂的昆虫烟碱能乙酰胆碱受体兴奋剂或拮抗剂 Download PDFInfo
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- CN1100537C CN1100537C CN95193465A CN95193465A CN1100537C CN 1100537 C CN1100537 C CN 1100537C CN 95193465 A CN95193465 A CN 95193465A CN 95193465 A CN95193465 A CN 95193465A CN 1100537 C CN1100537 C CN 1100537C
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Abstract
昆虫的烟碱能乙酰胆碱受体的兴奋剂或拮抗剂防治体内寄生虫的应用。
Description
本发明涉及用昆虫的烟碱能乙酰胆碱受体的兴奋剂或拮抗剂防治体内寄生虫。
昆虫的烟碱能乙酰胆碱受体的兴奋剂或拮抗剂是已知的。它们包括烟碱酰型杀虫剂，且特别是氯烟碱酰型杀虫剂。也已知道这些化合物具有突出的防治植食昆虫的作用。这些化合物防治植食昆虫时在植物中的全身作用也是已知的。
PCT申请WO93/24 002公开了某种1-[N-(卤代-3-吡啶基甲基)]-(N-甲基氨基-1-烷基氨基-2-硝基亚乙基衍生物适合用于防治家畜蚤的全身使用。在这种类型的应用中，此活性化合物是通过经口或非肠道途径(例如，通过注射)给药于家畜而达到家畜的血液的。蚤吸血时吸到活性化合物。然而，未见有关于这些化合物防治体内寄生虫作用的报道。
令人意外的是，现已发现，昆虫的烟碱能乙酰胆碱受体的兴奋剂或拮抗剂适合于防治体内寄生虫。
昆虫的烟碱能乙酰胆碱受体的兴奋剂或拮抗剂公开于，例如，欧洲专利公开申请464830，428941，425978，386565，383091，375907，364844，315826，259738，254859，235725，212600，192060，163855，154178，136636，303570，302833，306696，189972，455000，135956，471372，302389；德国专利公开369877，3712307；日本专利公开申请03220176，02207083，63307857，63287764，03246283，049374，03279359，03255072；美国专利5034524，4948798，4918086，5039686，5034404；PCT申请WO91/17659，91/4965；法国专利申请2611114；巴西专利申请8803621。
本文明确地给出这些文献中描述的方法、工艺、结构式和定义以及其中描述的个别制剂和化合物作为参考。
这些化合物优选用下列通式表示：其中R表示氢、选自酰基、烷基、芳基、芳烷基、杂芳基或杂芳基烷基的任选取代的基团；A表示选自氢、酰基、烷基和芳基的单官能基团或表示键合于Z基的双官能基团；E表示吸电子基；X表示-CH＝或＝N-基，其中-CH＝基也可以连于Z基而非一氢原子；Z表示选自烷基、-O-R、-S-R、
的单官能基团或表示键合于A基或X基的双官能基团。
特别优选的式(I)化合物是其中基团具有下列这些含意的化合物：R表示氢和选自酰基、烷基、芳基、芳烷基、杂芳基或杂芳基烷基的任选取代的基团；酰基可以提到的有甲酰基、烷基羰基、芳基羰基、烷基磺酰基、芳基磺酰基、(烷基-)-(芳基-)-磷酰基，所有这些基团可以被取代；烷基可以提到的有C1-10-烷基，特别是C1-4-烷基，具体的说是甲基、乙基、异丙基和仲丁基或叔丁基，所有这些基团可以被取代；芳基可以提到的有苯基和萘基，特别是苯基；芳烷基可以提到的有苯甲基和苯乙基；杂芳基可以提到的有达10个环原子和N、O和S，特别是N，作为杂原子的杂芳基，具体可以提到的有噻吩、呋喃、噻唑、咪唑、吡啶、苯并噻唑；杂芳基烷基可以提到的有具有达6个环原子和N、O和S，特别是N，作为杂原子的杂芳基甲基和杂芳基乙基；取代基可以以例子的方式提到的且优选的是：具有优选1至4个，特别是1或2个碳原子的烷基如甲基、乙基、正和异丙基和正、异和叔丁基；具有优选1至4个，特别是1或2个碳原子的烷氧基如甲氧基、乙氧基、正和异丙氧基和正、异和叔丁氧基；具有优选1至4个，特别是1或2个碳原子的烷硫基如甲硫基、乙硫基、正和异丙硫基和正、异和叔丁硫基；具有优选1至4个，特别是1或2个碳原子和优选1至5个，特别是1至3个卤原子的卤代烷基，卤原子可以相同或不同且优选表示氟、氯或溴，特别是氟，如三氟甲基；羟基、卤素，优选氟、氯、溴和碘，特别是氟、氯和溴；氰基、硝基；氨基；每个烷基具有优选1至4个，特别是1至2个碳原子的单烷基-和二烷基氨基，如甲氨基、甲基-乙氨基、正和异丙基氨基和甲基丁氨基；羧基，具有优选2至4个，特别是2或3个碳原子的烷氧羰基，如甲酯基、乙酯基；磺基(-SO3H)；具有优选1至4个，特别是1或2个碳原子的烷基磺酰基，如甲基磺酰基和乙基磺酰基；具有优选6或10个芳基碳原子的芳基磺酰基，如苯基磺酰基，和也可以是杂芳基氨基和杂芳基 烷基氨基，如氯吡啶氨基和氯吡啶甲基氨基。A特别优选代表氢和选自酰基、烷基和芳基的任选取代的基团，它们优选具有R中给定的含意。A还表示二官能基团。A基可以提到的是具有1-4个，特别是1-2个碳原子的任选取代的链烯基，取代基可以提到的是那些上面提到的取代基，且链烯基可以被选自N、O和S的杂原子间隔。A和Z与它们结合的原子一起形成饱和和不饱和杂环。这些杂环可以含有另外的1或2个相同或不同的杂原子和/或杂基团。杂原子优选代表氧、硫或氮，且杂基团优选代表N-烷基，N-烷基的烷基优选含有1至4个，特别是1或2个碳原子。烷基可以提到的有甲基、乙基、正和异丙基和正、异和叔丁基。杂环含有5至7个，优选5或6个环原子。可以提到的杂环的例子是吡咯烷、哌啶、哌嗪、六亚甲基亚胺、六氢-1，3，5-三嗪、吗啉，它们都可以被取代，特别是被甲基取代。E表示吸引电子的基团，可以提到的基团有，特别是，NO2、CN、卤代烷基羰基，如1，5-卤代-C1-4-羰基，特别是COCF3。X表示-CH＝或-N＝Z表示任选取代的烷基、-OR、-SR、-NRR或，R和取代基优选具有上面提到的含意。Z除上面提到的环外，还可与它所键合的原子和替代X的
一起可以形成饱和或不饱和的杂环。此杂环可以含有另外的1或2个相同或不同的杂原子和或杂基团。杂原子优选表示氧、硫或氮，且杂基团优选表示N-烷基，N-烷基中的烷基优选含有1至4个，特别是1或2个碳原子。烷基可以提到的是甲基、乙基、正和异丙基和正、异和叔丁基。杂环含有5至7个，特别是5或6个环原子。可以提到的杂环的例子是吡咯烷、哌啶、哌嗪、六亚甲基亚胺、吗啉和N-甲基哌嗪。
根据本发明非常特别适用的化合物是通式(II)和(III)的化合物：取代基
取代基
其中n表示1或2，取代基表示上面提到的取代基之一，特别是卤素，更特别是氯，A、Z、X和E具有上面提到的含义。
可以具体提到下列化合物：
这些活性化合物对温血动物的毒性低，适合于防治发现于人体和动物喂养和牲畜饲养、生产性动物、饲养动物、动物园动物、实验室动物、试验动物和宠物体内的病原体内寄生虫。在这些场合，它们对害虫的所有或个别发育阶段和对抗性和一般敏感种类有活性。通过防治病原体内寄生虫，旨在减少疾病、死亡和减产行为(例如在肉、奶、毛、皮、蛋、蜜等生产中)和(如果适宜)减少传染至人体，这样通过使用这些活性化合物使得更经济和简单的动物喂养成为可能。病原体内寄生虫包括绦虫、吸虫和线虫，特别是：
假叶目，例如，二叶槽虫(Diphyllobothrium spp.)、螺旋体虫(Spirometra spp.)、裂头绦虫(Schistocephalus spp.)、舌蜂蚴(Ligula spp.)、吸叶绦虫(Bothridium spp.)、Diphlogonoorus spp.。
圆叶目，例如，中孔绦虫(Mesocestoides spp.)、裸头绦虫(Anoplocephala spp.)、Paranoplocephala spp.、蒙尼绦虫(Monieziaspp.)、隧体绦虫(Thysanosmsa spp.)、Thysaniezia spp.、Avitellinaspp.、Stilesia spp.、鸣绦虫(Cittotaenia spp.)、Anhyra spp.、伯特绦虫(Bertiella spp.)、绦虫(Taenia spp.)、棘球绦虫(Echinococcusspp.)、Hydratigera spp.、斧钩绦虫(Davainea spp.)、瑞立绦虫(Raillietina spp.)、膜壳绦虫(Hymenolepsis spp.)、棘鳞绦虫(Echinolepsis spp.)、棘杯绦虫(Echinocotyle spp.)、两睾绦虫(Diorchis spp.)、复孔绦虫(Dipylidium spp.)、Joyeuxiella spp.、Diplopylidium spp.。
单殖亚纲，例如，Cyrodactylus spp.、指环虫(Dactylogyrusspp.)、多盘属(Polystoma spp.)。
复殖亚纲，例如，复口吸虫(Diplostomum spp.)、后口吸虫(posthodiplostomum spp.)、裂体吸虫(Schistosoma spp.)、毛睾吸虫(Trichobilharzia spp.)、鸟毕吸虫(Ornithobilharzia spp.)、澳吸虫(Austrobilharzia spp.)、巨吸虫(Gigantobilharzia spp.)、彩蚴吸虫(Leucochloridium spp.)、短咽吸虫(Brachylaima spp.)、棘颈吸虫(Echinostoma spp.)、棘缘吸虫(Echinoparyphium spp.)、棘隙吸虫(Echinochasmus spp.)、低颈吸虫(Hypoderaeum spp.)、片形吸虫(Fasciola spp.)、拟片形吸虫(Fascioloides spp.)、姜片虫(Fasciolopsis spp.)、环肠吸虫(Cyclocoelum spp.)、盲腔吸虫(Typhlocoelum spp.)、同端盘吸虫(Paramphistomum spp.)、杯殖吸虫(Calicophoron spp.)、殖盘吸虫(Cotylophoron spp.)、巨孔吸虫(Gigantocotyle spp.)、菲吸虫(Fischoederius spp.)、食羊胃吸虫(Gastrothylacus spp.)、背孔吸虫(Notocotylus spp.)、Catatropis spp.、斜睾吸虫(Plagiorchis spp.)、前殖吸虫(Prosthogonismus spp.)、双腔吸虫(Dicrocoelium spp.)、饼吸虫(Collyriculum spp.)、隐孔吸虫(Nanophyetus spp.)、后睾吸虫(Opisthorchis spp.)、枝睾吸虫(Clonorchis spp.)、次睾吸虫(Metorchis spp.)、异形吸虫(Heterophyes spp.)、后殖吸虫(Metagonimus spp.)。
嘴刺目，例如，鞭虫(Trichuris spp.)、毛线虫(Capillaria spp.)、Trichlomosoides spp.、毛形线虫(Trichinella spp.)。
小杆目，例如，微颈线虫(Micronema spp.)、类圆线虫(Strongyloides spp.)。
圆线虫目，例如，圆线虫(Strongylus spp.)、三齿线虫(Triodontophorus spp.)、结齿线虫(Oesophagodontus spp.)、毛线线虫(Trichonema spp.)、似六齿线虫(Gyalocephalus spp.)、筒咽线虫(Cylindropharynx spp.)、Poteriostromum spp.、Cyclococercus spp.、Cylicostephanus spp.、Oesophagostomum spp.、夏柏线虫(Chabertia spp.)、肾线虫(Stephanurus spp.)、Acylostomaspp.、钩虫(Uncinaria spp.)、仰口线虫(Bunostomum spp.)、球头线虫(Globocephalus spp.)、比翼线虫(Syngamus spp.)、杯口线虫(Cyathostoma spp.)、后圆线虫(Metastrongylus spp.)、网属线虫(Dictyocaulus spp.)、米勒线虫(Muellerius spp.)、原圆线虫(Protostrongylus spp.)、新圆线虫(Neostrongylus spp.)、囊柄线虫(Cystocaulus spp.)、肺圆线虫(Pneumostrongylus spp.)、针柄线虫(Spicocaulus spp.)、Elaphostrongylus spp.、Parelaphostrongylus spp.、环体线虫(Crenosoma spp.)、拟环体线虫(Paracrenosoma spp.)、管圆线虫(Angiostrongylus spp.)、猫圆线虫(Aelurostrongylus spp.)、类丝线虫(Filaroides spp.)、拟类线虫(Parafilaroides spp.)、毛圆线虫(Trichostrongylus spp.)、血矛线虫(Haemonchus spp.)、奥斯脱线虫(Ostertagia spp.)、马歇尔线虫(Marshallagia spp.)、古柏线虫(Cooperia spp.)、细颈线虫(Nematodirus spp.)、下圆线虫(Hyostrongylus spp.)、方尖线虫(Obeliscoides spp.)、裂口线虫(Amidostomum spp.)、Ollulanusspp.。
尖尾线虫目，例如，尖尾线虫(Oxyuris spp.)、蛲虫(Enterobiusspp.)、栓尾线虫(Passalurus spp.)、管状线虫(SyPhacia spp.)、Aspiculuris spp.、异刺线虫(Heterakis spp.)。
蛔虫目，例如，蛔虫(Ascaris spp.)、毒蛔虫(Toxascaris spp.)、弓蛔虫(Toxocara spp.)、副蛔虫(Parascaris)、无饰蛔虫(Anisakisspp.)、鸡蛔虫(Ascaridia spp.)。
旋尾目，例如，颚口线虫(Gnathostoma spp.)、泡翼线虫(Physaloptera spp.)、吸吮线虫(Thelazia spp.)、胃线虫(Gongylonerma spp.)、Parabronema spp.、德斯线虫(Draschiaspp.)、龙线虫(Dracunculus spp.)。
丝虫目，例如，冠丝虫(Stephanofilaria spp.)、拟丝虫(Parafilariaspp.)、腹腔线虫(Setaria spp.)、恶丝虫(Dirofilaria spp.)、劳丝虫(Lao spp.)、光丝虫(Litomosoides spp.)、布鲁线虫(Brugiaspp.)、吴策线虫(Wuchereria spp.)、盘尾线虫(Onchocerca spp.)。
大棘吻目，例如，丝棘虫(Filicollis spp.)、链球棘虫(Moniliformis spp.)、巨吻棘虫(Macracanthorhynchus spp.)、前隐睾棘虫(Prosthenorchis spp.)。
生产性牲畜和饲养动物包括哺乳动物如，例如，牛、马、绵羊、猪、山羊、骆驼、水牛、驴、兔子、黇鹿、驯鹿，皮毛动物如，例如，水貂、灰鼠、浣熊，鸟如，例如，鸡、鹅、火鸡和鸭。
实验室动物和试验动物包括如小鼠、大鼠、豚鼠、金仓鼠狗和猫。
宠物包括狗和猫。
可预防以及治疗给药。
活性化合物给药可以是下列各种形式：直接或以适合的制剂形式经肠道、非肠道、经皮、经鼻给药，通过环境处理给药，或在含有活性化合物的成形物件的辅助下给药，成形物件如条、板、带、颈圈、耳记物、圈带和标记物。
活性化合物可以如下形式经肠道(如经口)给药：粉剂、栓剂、片剂、胶囊、膏剂、饮品、颗粒、药水、药团、药物进食或饮用水。以如下形式经皮给药是有效的：例如，蘸浸、喷雾、洗澡、冲洗、浇泼、点涂和喷粉。以下列形式非肠道给药是有效的：例如，注射(肌内、皮下、静脉、腹腔内)或植入。
适合的制剂是：
溶液如注射溶液，或口服溶液，稀释后口服的浓缩物，用在皮肤和体腔内的溶液，浇泼和点涂制剂、凝胶。
用于口服或皮施和用于注射的乳液和悬浮剂，半固体制剂。
活性化合物掺入霜基料或水包油或油包水乳液基料中的剂型。
固体制剂如粉剂、预混物或浓缩物、颗粒剂、丸剂、片剂、药团、胶囊；气雾剂和吸入剂，含活性化合物的成形物件。
可注射溶液经静脉、肌内和皮下给药。
可注射溶液通过将活性化合物溶于适合的溶剂和(如果适宜)加入添加剂如增溶剂、酸、碱、缓冲盐、抗氧剂和防腐剂而制备。此溶液是消毒过滤和除多余水份的。
作为溶剂可提到的有下列：生理上可接受的溶剂如水，醇类如乙醇、丁醇、苯甲醇、甘醇，烃类，丙二醇，聚乙二醇，N-甲基-吡咯烷酮，及其混合物。
如果适宜，活性化合物也可以溶于生理上可接受的适于注射的植物油和合成油。
作为增溶剂可以提到的有下列：提高活性化合物在主溶剂中的溶解度的溶剂，或防止其沉淀的溶剂。例子有：聚乙烯吡咯烷酮、聚氧乙烯化蓖麻油、聚氧乙烯化脱水山梨醇酯。
防腐剂是：苯甲醇、三氯丁醇、对羟基苯甲酸酯、正丁醇。
口服溶液是直接服用。浓缩物是在预先稀释到给药浓度后口服。口服溶液和浓缩物按照上述在可注射溶液中描述的方法制备，也可以是在消毒条件下配药。
用在皮肤上的溶液提高通过点滴、刷涂、擦涂、溅泼、或沉浸(蘸浸、洗澡或冲洗)来施用。这些溶液按照可注射溶液中描述的方法制备。
在配制的过程中添加增稠剂会是有利的。增稠剂是：无机增稠剂如膨润土、胶体二氧化硅、单硬脂酸铝，有机增稠剂如纤维素衍生物、聚乙烯醇及其共聚物、丙烯酸盐(酯)或甲基丙烯酸盐(酯)。
凝胶是涂或刷在皮肤上，或导入体腔。凝胶是通过用能形成霜样稠度的透明物质的增稠剂量来处理预先按照可注射溶液中描述的方法制备的溶液来制备的。采用的增稠剂是上面提到的增稠剂。
浇泼和点涂剂型是浇泼到或溅泼到皮肤限定的区域，活性化合物或是渗透入皮肤或是全身作用或是经分布整个身体表面。
浇泼和点涂剂型是通过将活性化合物溶解、悬浮或乳化于皮肤可耐受的适宜溶剂或溶剂混合物中而制备的。如果适宜，可加入其它辅助剂如着色剂、吸收加速剂、抗氧剂、抗光剂和增粘剂。
可以提到的溶剂有：水，链烷醇类，二醇类，聚乙二醇类，聚丙二醇类，甘油，芳族醇类如苯甲醇、苯乙醇、苯氧乙醇，酯类如乙酸乙酯、乙酸丁酯、苯甲酸苄酯，醚类如烷二醇烷基醚如双丙甘醇单甲基醚、二甘醇单丁基醚，酮类如丙酮、甲乙酮，芳族和/或脂族烃，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-氧代-亚甲基-1，3-二氧戊环。
着色剂是所有的允许用在动物上且可以溶解或悬浮的着色剂。
吸收加速剂的例子是DMSO，扩散油类如异丙基肉豆蔻酯、双丙甘醇壬酸酯，硅油类，脂肪酸酯类，甘油三酯类，脂肪醇类。
抗氧剂是亚硫酸盐或偏亚硫酸氢盐如偏硫酸氢钾，抗坏血酸，丁基羟基甲苯、丁基羟基茴香醚，生育酚。
抗光剂的例子选自二苯酮或苯基苯并咪唑磺酸。
增粘剂的例子是纤维素衍生物，淀粉衍生物，聚丙烯酸酯(盐)，天然聚合物如藻酸盐、明胶。
乳液可以经口、经皮或以注射形式给药。
乳液是油包水型或是水包油型。
它们可以如下制备：将活性化合物溶于疏水或是亲水相，并且借助适合的乳化剂用另一相的溶剂来均化此相，且如果适宜，也可有其它辅助剂如着色剂、吸收加速剂、防腐剂、抗氧剂、抗光剂和增粘剂。
作为疏水相(油)可以提到的有下列：石蜡油类，硅油类，天然植物油类如芝麻油、杏仁由、蓖麻油，合成甘油三酯类如辛酸/己酸二甘油酯，甘油三酯与链长C8-12的植物脂肪酸或与其它特别是选自天然脂肪酸的混合物，可含有羟基基团的饱和或不饱和脂肪酸的部分甘油酯混合物，和C8-C10-脂肪酸的单或二甘油酯。
脂肪酸如硬脂酸乙酯、二正丁炔基己二酸酯、月桂酸己酯、双丙甘醇壬酸酯、中长链支链脂肪酸与链长C16-C18-饱和脂肪醇的酯、肉豆蔻异丙基酯、棕榈酸异丙基酯、链长C8-12的饱和脂肪醇的辛酸/己酸酯、硬脂酸异丙基酯、油酸油醇酯、油酸癸酯、油酸乙酯、乳酸乙酯、蜡状脂肪酸酯如人造duck preen fat、邻苯二甲酸二丁酯、己二酸二异丙酯、与后者相关的酯混合物。
脂肪醇如异十三烷醇、2-辛基-十二烷醇醇、鲸蜡基硬脂基醇、油醇。
脂肪酸如油酸及其混合物。
作为亲水相可以提到的有下列：水，醇如丙二醇、甘醇、山梨醇及其混合物。
作为乳化剂可以提到的有下列：非离子表面活性剂，例如，聚氧乙烯化蓖麻油、聚氧乙烯化失水山梨醇单油酸酯、失水山梨醇单硬脂酸酯、甘醇单硬脂酸酯、聚氧乙烯硬脂酸酯、烷基酚聚乙二醇醚。
两性表面活性剂如N-月桂基-β-亚氨基二丙酸二钠或卵磷脂。
阴离子表面活性剂如十二烷基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚乙二醇醚正磷酸酯的单乙醇胺盐。
阳离子表面活性剂如癸基三甲基铵氯化物。
其它辅助剂可以提到的有下列：增粘物质和稳定乳液的物质，如羧甲基纤维素、甲基纤维素和其它纤维素和淀粉衍生物、聚丙烯酸酯、藻酸盐、明胶、阿拉伯胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯基醚和马来酸酐的共聚物、聚乙二醇、蜡、胶体二氧化硅、或所提的物质的混合物。
悬浮剂可以经口、经皮或以注射的形式给药。它们通过将活性物质悬浮于赋形剂液体，如果适宜，添加其它的辅助剂如润湿剂、着色剂、吸收加速剂、防腐剂、抗氧剂和抗光剂来制备。
赋形剂液体可以提到的是所有均质溶剂和溶剂混合物。
润湿剂(分散剂)可以提到的是上面指明的那些表面活性剂。
其它助剂可提及上述那些。
半固体制剂可以经口或经皮给药。它们只是在更高的粘度这一点上与上述悬浮液和乳液有所区别。
为制备固体制剂，将活性化合物与适宜的赋形剂混合，如果适宜，可添加辅助剂，并且将混合物按照所需的加工。
赋形剂可以提到的是所有生理上可接受的固体惰性物质。适宜的是无机和有机物质。无机物质的例子是氯化钠、碳酸盐如碳酸钙、碳酸氢盐、铝氧化物、二氧化硅、陶土、沉淀和胶体二氧化硅、和磷酸盐。
有机物质的例子是糖、纤维素、食物和动物饲料如奶粉、动物食料和谷粉和粗谷粉和淀粉。
辅助剂是上面已经提到的防腐剂、抗氧剂和着色剂。
其它适合的辅助剂是润滑剂和润滑剂(glidant)如硬脂酸钙、硬脂酸、滑石、膨润土，崩解剂如淀粉或交联的聚乙烯吡咯烷酮，粘合剂如淀粉、明胶或直链聚乙烯吡咯烷酮，和干的粘合剂如微晶纤维素。
在制剂中，活性化合物也可以以与增效剂或与其它的抗病原体内寄生虫的活性化合物的混合物的形式存在。这些活性化合物的例子是L-2，3，5，6-四氢-6-苯基咪唑噻唑、苯并咪唑氨基甲酸酯、吡喹酮、噻嘧啶、非班太。
即用制剂中活性化合物的浓度为10ppm至20％(按重量计)，优选0.1至10％(按重量计)。
给药前要稀释的制剂中活性化合物的浓度为0.5至90％(按重量计)，优选5至50％(按重量计)。
通常，业已证明，以大致1至100mg活性化合物/公斤体重每日的量给药是有利的，可获取有效的效果。
在下列实施例中，采用的活性化合物是咪蚜胺＝1-[(6-氯-3-吡啶基)甲基]-N-硝基-咪唑烷基亚胺。实施例1SC(悬浮剂浓缩剂)剂型368g 咪蚜胺35g 乳化剂、环氧乙烷和环氧丙烷的嵌段共聚物12g 二甲苯基醚磺酸酯/甲醛缩合物(乳化剂)3.5g 水溶性聚乙烯醇58.0g NH4Cl116.0g 尿素1.2g (37％盐酸水溶液)4.6g 黄原胶560.5g 蒸馏水实施例2WP(可分散粉剂)剂型25.0g 咪蚜胺1.0g 二异丁基萘磺酸钠10.0g 正十二烷基苯磺酸钙12.0g 含高分散硅胶的烷基芳基聚乙二醇醚3.0g 二甲苯基醚磺酸酯/甲醛缩合物(乳化剂)2.0g Baysilon-E，Bayer AG生产的含硅酮的消泡剂2.0g 高分散二氧化硅，和45.0g 高岭土实施例3SL(水溶性浓缩剂)剂型 18.3g 咪蚜胺2.5g 以烷基芳基聚乙二醇醚为基础的中性乳化剂3.5g 二异辛基磺基琥珀酸钠38.4g 二甲基亚砜，和37.5g 2-丙醇实施例4SL(水溶性浓缩剂)剂型185g 咪蚜胺5.0g 二异辛基磺基琥珀酸钠，和76.5g -二甲基亚砜加入100g由下列组成的香波：44.4％ (按重量计)Marlon AT50，一种烷基苯磺酸的三乙醇胺盐
由Huls AG生产11.1％ (按重量计)Marlon A350，烷基苯磺酸的钠盐，由Hüls AG
左产3.0％ (按重量计)油酸和二乙醇胺的缩合产物，由Hüls AG生
产41.5％ (按重量计)聚乙二醇实施例5由下列组成的喷雾剂：2.0g 咪蚜胺10.0g 二甲基亚砜35.0g 2-丙醇，和53.0g 丙酮实施例A线虫体内试验绵羊旋血矛线虫(Haemonchus contortus)试验
在寄生虫显露前期过后，治疗由旋血矛线虫实验感染的绵羊。活性化合物以在明胶中的纯活性化合物形式口服施用。
对治疗前和后排泄的粪便中蠕虫的卵量评价来测定效果。
如果治疗后，卵排泄完全停止，这就意味着虫被败育或被伤害至不再产卵的程度(有效剂量)。
试验活性化合物和有效剂量可以由下表看到：
活性化合物 有效剂量(mg/Kg)
咪蚜胺 10实施例B小鼠短膜壳绦虫(Hymenolepis nana)试验
由来自节片的感染卵经口试验感染。在寄生虫显露前期过后，实施治疗(在随后4天治疗4次，口服)。7天后，检测肠中头节的数量。效果用下式计算：
对照组中的头节数-处理组中的头节数％效果＝———————————————————
对照组中的头节数活性化合物：咪蚜胺；效果：口服25mg/Kg时，效果100％。
Claims (6)
1.昆虫烟碱能乙酰胆碱受体的兴奋剂或拮抗剂在防治被体内寄生虫侵害的温血动物体内寄生虫的药物生产中的用途，其中所述兴奋剂或拮抗剂选自具有下列结构的化合物：
其中，
n代表1或2，
取代基代表卤素，
A和Z与它们所连接的原子一起形成饱和或不饱和的杂环，该杂环任选含有1或2个氮原子和/或N-烷基，其中烷基含有1-4个碳原子，
X代表N＝，
E代表吸引电子的基团。
2.权利要求1的用途，其中n代表1。
3.权利要求1的用途，其中取代基代表氯。
4.权利要求1的用途，其中所述杂环代表比咯烷、哌啶、哌嗪、六亚甲基亚胺、六氢-1，3，5-三嗪。
5.权利要求1的用途，其中E代表NO2。
6.权利要求3的用途，其中所述兴奋剂或拮抗剂为下式的化合物：
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| DEP4419814.0 | 1994-06-07 | ||
| DE4419814A DE4419814A1 (de) | 1994-06-07 | 1994-06-07 | Endoparasitizide |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95193465A Expired - Fee Related CN1100537C (zh) | 1994-06-07 | 1995-05-26 | 用作杀体内寄生虫剂的昆虫烟碱能乙酰胆碱受体兴奋剂或拮抗剂 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5712295A (zh) |
| EP (1) | EP0764022B1 (zh) |
| JP (1) | JP3978227B2 (zh) |
| KR (1) | KR100372348B1 (zh) |
| CN (1) | CN1100537C (zh) |
| AT (1) | ATE348604T1 (zh) |
| AU (1) | AU704092B2 (zh) |
| BR (1) | BR9507926A (zh) |
| CA (1) | CA2192093C (zh) |
| DE (2) | DE4419814A1 (zh) |
| DK (1) | DK0764022T3 (zh) |
| ES (1) | ES2279513T3 (zh) |
| MX (1) | MX9606179A (zh) |
| WO (1) | WO1995033453A1 (zh) |
| ZA (1) | ZA954643B (zh) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4443888A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | Dermal applizierbare Formulierungen von Parasitiziden |
| US6426333B1 (en) * | 1996-09-19 | 2002-07-30 | Merial | Spot-on formulations for combating parasites |
| DE19654079A1 (de) * | 1996-12-23 | 1998-06-25 | Bayer Ag | Endo-ekto-parasitizide Mittel |
| FR2761232B1 (fr) * | 1997-03-26 | 2000-03-10 | Rhone Merieux | Procede et moyens d'eradication des puces dans les locaux habites par les petits mammiferes |
| DE19734665A1 (de) * | 1997-08-11 | 1999-02-18 | Bayer Ag | Mittel gegen holzzerstörende Insekten |
| DE19807630A1 (de) * | 1998-02-23 | 1999-08-26 | Bayer Ag | Wasserhaltige Mittel zur Bekämpfung parasitierender Insekten und Milben an Menschen |
| US6727228B2 (en) * | 2001-04-25 | 2004-04-27 | Johnson & Johnson Consumer Companies, Inc. | Pediculicidal and ovacidal treatment compositions and methods for killing head lice and their eggs |
| MX2007006534A (es) * | 2004-12-17 | 2007-07-25 | Devgen Nv | Composiciones nematicidas. |
| US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
| US9820977B2 (en) * | 2008-10-03 | 2017-11-21 | Bayer Healthcare Llc | Systemic treatment of blood-sucking and blood-consuming parasites by oral administration of a parasiticidal agent |
| US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
| CA2989391C (en) | 2014-06-24 | 2023-03-14 | John O'halloran | Fish feed compositions containing a neonicotinoid for preventing and treating parasite infections |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0590425A1 (de) * | 1992-09-29 | 1994-04-06 | Bayer Ag | Bekämpfung von Fischparasiten |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA689474A (en) * | 1964-06-23 | Clarence H. Gleason | Nicotine pamoate | |
| JPS60172976A (ja) * | 1984-02-16 | 1985-09-06 | Nippon Tokushu Noyaku Seizo Kk | ニトロメチレン誘導体，その製法及び殺虫，殺ダニ，殺センチユウ剤 |
| ZW5085A1 (en) * | 1984-04-13 | 1985-09-18 | Nihon Tokushu Noyaku Seizo Kk | Nitromethylene derivatives,intermediates thereof,processes for production thereof,and insecticides |
| DE3681465D1 (zh) * | 1985-02-04 | 1991-10-24 | Nihon Bayer Agrochem K.K., Tokio/Tokyo, Jp | |
| JPH07121909B2 (ja) * | 1986-09-10 | 1995-12-25 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物及び殺虫剤 |
| JP3023794B2 (ja) * | 1989-05-17 | 2000-03-21 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロ置換ヘテロ環式化合物 |
-
1994
- 1994-06-07 DE DE4419814A patent/DE4419814A1/de not_active Withdrawn
-
1995
- 1995-05-26 DE DE59511073T patent/DE59511073D1/de not_active Expired - Fee Related
- 1995-05-26 EP EP95922486A patent/EP0764022B1/de not_active Expired - Lifetime
- 1995-05-26 AT AT95922486T patent/ATE348604T1/de not_active IP Right Cessation
- 1995-05-26 BR BR9507926A patent/BR9507926A/pt not_active Application Discontinuation
- 1995-05-26 CN CN95193465A patent/CN1100537C/zh not_active Expired - Fee Related
- 1995-05-26 WO PCT/EP1995/002014 patent/WO1995033453A1/de active IP Right Grant
- 1995-05-26 MX MX9606179A patent/MX9606179A/es not_active IP Right Cessation
- 1995-05-26 ES ES95922486T patent/ES2279513T3/es not_active Expired - Lifetime
- 1995-05-26 AU AU27364/95A patent/AU704092B2/en not_active Ceased
- 1995-05-26 DK DK95922486T patent/DK0764022T3/da active
- 1995-05-26 CA CA002192093A patent/CA2192093C/en not_active Expired - Fee Related
- 1995-05-26 US US08/750,012 patent/US5712295A/en not_active Expired - Lifetime
- 1995-05-26 KR KR1019960706908A patent/KR100372348B1/ko not_active IP Right Cessation
- 1995-05-26 JP JP50029796A patent/JP3978227B2/ja not_active Expired - Lifetime
- 1995-06-06 ZA ZA954643A patent/ZA954643B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0590425A1 (de) * | 1992-09-29 | 1994-04-06 | Bayer Ag | Bekämpfung von Fischparasiten |
Also Published As
| Publication number | Publication date |
|---|---|
| US5712295A (en) | 1998-01-27 |
| KR100372348B1 (ko) | 2003-05-12 |
| CA2192093C (en) | 2007-05-22 |
| CN1149827A (zh) | 1997-05-14 |
| CA2192093A1 (en) | 1995-12-14 |
| EP0764022A1 (de) | 1997-03-26 |
| EP0764022B1 (de) | 2006-12-20 |
| ATE348604T1 (de) | 2007-01-15 |
| DE4419814A1 (de) | 1995-12-14 |
| ES2279513T3 (es) | 2007-08-16 |
| DK0764022T3 (da) | 2007-04-10 |
| AU704092B2 (en) | 1999-04-15 |
| JPH10500699A (ja) | 1998-01-20 |
| WO1995033453A1 (de) | 1995-12-14 |
| AU2736495A (en) | 1996-01-04 |
| ZA954643B (en) | 1996-01-26 |
| BR9507926A (pt) | 1997-11-11 |
| MX9606179A (es) | 1998-01-31 |
| JP3978227B2 (ja) | 2007-09-19 |
| DE59511073D1 (de) | 2007-02-01 |
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Legal Events
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| C06 | Publication | ||
| PB01 | Publication | ||
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| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: BAYER ANIMAL HEALTH PROMOTION CO.,LTD. Free format text: FORMER OWNER: BAYER AG Effective date: 20091106 |
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| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20091106 Address after: Germany Leverkusen Patentee after: Bayer Animal Health GmbH Address before: Germany Leverkusen Patentee before: Bayer Aktiengesellschaft |
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| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20030205 Termination date: 20100526 |