CN1211245A - 咪唑啉衍生物的盐及其作为害物防治剂的用途 - Google Patents
咪唑啉衍生物的盐及其作为害物防治剂的用途 Download PDFInfo
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- CN1211245A CN1211245A CN97192241A CN97192241A CN1211245A CN 1211245 A CN1211245 A CN 1211245A CN 97192241 A CN97192241 A CN 97192241A CN 97192241 A CN97192241 A CN 97192241A CN 1211245 A CN1211245 A CN 1211245A
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- salt
- alkyl
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- imidazolidine derivatives
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Abstract
本发明涉及新的通式(Ⅰ)的咪唑啉衍生物的盐以及它们的制备和作为害物防治剂的用途,其中R代表氢或烷基,Y代表硝基或氰基,W代表一个任意选择取代的5或6元杂环基和Z代表一价的碱金属或碱土金属或一个[NR1R2R3R4]基,其中R1,R2,R3和R4是相同的或不相同的和代表氢,烷基,任意选择取代的环烷基或任意选择取代的苄基。
Description
本发明涉及新的咪唑啉衍生物的盐,它们的制备方法以及防治动物害物的用途
已知一些烷基取代的咪唑啉衍生物,例如1-(2-氯嘧啶-5-基)-3-甲基-2-硝基亚胺咪唑啉,具有杀虫活性(参见,例如EP-A 0 315 826)。可是,这些化合物的活性和作用范围总是不能令人完全满意,特别是在低用量和低浓度的时候。
其中
R代表氢或烷基,
Y代表硝基或氰基,
W代表一个任意选择取代的5-或6-元杂环基和
Z代表一价的碱金属或碱土金属或一个[NR1R2R3R4]基团,其中
R1,R2,R3和R4是相同的或不相同的和代表氢,烷基,任意选择取代的环烷基或任意选择取代的苄基。
而且已经发现通式(Ⅰ)的咪唑啉衍生物的盐可以通过以下方法,即在稀释剂存在下由通式(Ⅱ)的咪唑啉
其中
R,Y和W的含义如上述,
与通式(Ⅲ)的氢氧化物反应制得。
Z-OH (Ⅲ)
其中
Z的含义如上述。
最后,已经发现新的通式(Ⅰ)咪唑啉衍生物的盐具有高的明显的生物特性,和首先适宜于防治动物害物,特别是在农业,森林,贮存产品和材料的防腐以及卫生方面的害虫,蜘蛛纲动物和线虫。
通式(Ⅰ)提供了本发明的咪唑啉衍生物的盐的一般定义。
列于上面和下面所述的通式中的优选取代基和基团范围说明如下。
R优选代表氢或C1-C4烷基。
Y优选代表硝基和氰基。
W优选代表5-或6-元杂环基其中含有1或2个不同或相同的杂原子,例如,优选氮,氧或硫原子,并以不同或相同的方式被任意选择取代1至3次,
可以说明的取代基是:
卤素,C1-C4烷基,C1-C4烷氧基,C1-C4卤代烷基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4烷基亚磺酰基,C1-C4烷基磺酰基,C1-C4卤代烷硫基,C1-C4卤代烷基亚磺酰基,C1-C4卤代烷基磺酰基或C1-C2烯基。
Z在各种情况下部优选代表一价的锂,钠,钾,铷,铯,镁,钙,铵,C1-C4烷基铵,二(C1-C4烷基)铵,三(C1-C4烷基)铵,四(C1-C4烷基)铵,C5或C6环烷基铵或二(C1-C2烷基)苄铵。
R特别优选代表氢和甲基。
Y特别优选代表硝基或氰基。
W在各种情况下特别优选代表任意选择取代的吡啶基,噻唑基,噁唑基,异噻唑基或异噁唑基,可说明的取代基是:
氟,氯,溴,甲基,乙基,三氟甲基,甲氧基,三氟甲氧基,甲硫基,甲基亚磺酰基或甲基磺酰基。
Z在各种情况下特别优选代表一价的锂,钠,钾,铷,铯,镁,钙,铵,甲基铵,二甲基铵,三甲基铵,四甲基铵,四乙基铵,四正丙基铵,四正丁基铵或二甲基苄铵。
其中
Z代表上述的一般、优选和特别优选的含义。
基团的定义和解释如上所列,或是一般的或是优选的范围应用于相应的最终产品和起始物和中间体。如果需要,这些基团的定义可以相互合并,所以也包括分别的优选范围之间的合并。
本发明优选的通式(Ⅰ)化合物就是其中优选含有上述定义的合并的化合物。
本发明特别优选的通式(Ⅰ)化合物就是其中特别优选含有上述定义的合并的化合物。
在上面和下面所列的基团的定义中,烃基,例如烷基或烯基-包括与杂原子合并的,如烷氧基或烷硫基在每种情形中,可能各自为直链或支链的。
在本发明的方法中用作起始物质的通式(Ⅱ)的咪唑啉是已知的(参见,例如,EP-A 0 259 738和EP-A 0 135 826),和/或它们可以通过已知的方法制得(参见,例如,上述参考文献)。
而且在本发明的方法中用作起始物质的通式(Ⅲ)的氢氧化物一般也是已知的化合物。
本发明的方法在稀释剂存在下进行。优选使用的稀释剂是水和有机的/水的体系,所有通常的水溶性有机溶剂均可采用。可说明的实例是酮类,例如丙酮,甲乙酮或甲基异丁基酮;腈类,例如乙腈或丙腈,和醇类,例如甲醇或乙醇。
在本发明的方法中反应温度可在大范围内变动。一般反应在0和100℃之间,优选0和60℃之间进行。
在本发明的方法的实施中,对于每摩尔通式(Ⅱ)的咪唑啉一般采用0.9~1.5摩尔,优选0.95~1.2摩尔或等摩尔的通式(Ⅲ)氢氧化物。
最终产品的后处理和分离一般按照已知的方法进行。
在某些情况下,采用通式(Ⅲ)化合物的醇化物形式是有好处的。
活性化合物适用于防治动物害物,特别是害虫、蜘蛛纲类动物和线虫,它们存在于农业中,森林中,贮存产品和材料的贮藏中,以及卫生领域中,并具有良好的植物耐药量与对温血动物的可接受的毒性。它们被优选用作植物保护剂。它们对通常的敏感品系和抗性品系和所有的或某些发育阶段的(害物)均有效。
包括等足目,例如,潮虫,平甲虫,鼠妇(Porcellio scaber)。
倍足目,例如,食果地蜈蚣,蚰蜓。
综合目,例如,庭院么蚰。
缨尾目,例如,西洋衣鱼。
弹尾目,例如,武装棘跳虫。
直翅目,例如,东方蜚蠊,美洲大蠊,马得拉蜚蠊,德国小蠊,家蟋蟀,蝼蛄属,非洲飞蝗,异黑蝗和沙漠蝗。
革翅目,例如,欧洲球螋。
等翅目,例如,散白蚁属。
虱目,例如,体虱,血虱属和长颚虱属。
食毛目,例如,嚼虱属和畜虱属。
缨翅目,例如,温室条蓟马和烟蓟马。
半翅目,例如,扁盾蝽属,棉红蝽,方背皮蝽,温带臭虫,长红猎蝽和椎猎蝽属。
同翅目,例如,甘蓝粉虱,甘薯粉虱,温室粉虱,棉蚜,甘蓝蚜,茶藨隐瘤蚜,豆卫矛蚜,苹果蚜,苹果绵蚜,桃大尾蚜,葡萄根瘤蚜,瘿绵蚜属,麦长管蚜,瘤蚜属,忽布疣蚜,禾谷缢管蚜,微叶蝉属,纹叶蝉,黑尾叶蝉,欧果坚球蚧,橄榄黑盔蚧,灰飞虱,褐飞虱,红肾圆盾蚧,常春藤圆盾蚧,粉蚧属和木虱属。
鳞翅目,例如,棉红蛉虫,松粉蝶尺蛾,果园秋尺蛾,苹细蛾,苹果巢蛾,小菜蛾,黄褐天幂毛虫,黄毒蛾,毒蛾属,棉潜蛾,柑桔潜叶蛾,地夜蛾属,切夜蛾属,褐夜蛾属,埃及金刚钻,实夜蛾属,贪夜蛾,甘蓝夜蛾,小眼夜蛾,斜蚊贪夜蛾,贪夜蛾属,粉夜蛾属,苹果小卷蛾,菜粉蝶属,禾草螟属,玉米螟,地中海粉斑螟,大蜡螟,幕谷蛾,袋谷蛾,福织蛾,亚麻黄卷蛾,烟卷蛾,枞色卷蛾,葡萄果蠹蛾,茶长卷蛾,栎绿卷蛾。
鞘翅目,例如家具切蠹,谷蠹,豆象,茶豆象,北美家天牛,杨树萤叶甲,马铃薯叶甲,辣根猿叶甲,叶甲属,油菜金头跳甲,墨西哥大豆瓢虫,稳食甲属,锯谷盗,花象属,谷象属,黑葡萄耳象,香蕉根颈象,白菜籽龟象,紫苜蓿叶象,皮蠹属,斑皮蠹属,圆皮蠹属,毛皮蠹属,粉蠹属,油菜露尾甲,蛛甲属,黄蛛甲,裸蛛甲,拟谷盗属,黄粉虫,叩头虫属,宽胸叩头虫属,西方五月鳃角金龟,马铃薯鳃角金龟和褐新西兰肋翅鳃角金龟。
膜翅目,例如锯角叶蜂属,实叶蜂属,毛蚁属,小黄家蚁和胡蜂属。
双翅目,例如伊蚊属,按蚊属,库蚊属,黑尾果蝇,家蝇属,厕蝇属,红头丽蝇,绿蝇属,金蝇属,疽蝇属,胃蝇属,虱蝇属,厩螯蝇属,狂蝇属,皮蝇属,虻属,螗蜩属,毛蚊,瑞典麦杆蝇,草种蝇属,甜菜泉蝇,地中海蜡实蝇,橄榄大实蝇和欧洲大蚊。
蚤目,例如印鼠客蚤和角叶蚤属。
蛛形纲目,例如蝎和盗蛛和红蜘蛛。
蜱螨目,例如粗脚粉螨,锐缘蜱属,钝缘蜱属,鸡皮刺螨,茶蔗瘿螨,桔芸锈螨,牛蜱属,扇头蜱属,花蜱属,璃眼蜱属,硬蜱属,痒螨属,痒螨,疥螨属,跗线螨属,苜蓿苔螨,全爪螨属和叶螨属。
植物寄生线虫包括,例如,短体线虫属,相似穿孔线虫,起绒草茎线虫,半穿刺线虫,异皮线虫属,球异皮线虫属,根结线虫属,滑刃线虫属,长针线虫属,剑线虫属和毛刺线虫属。
本发明的通式(Ⅰ)化合物特别是以高杀虫活性著名的。
它们可以特别成功地用于防治危害植物的昆虫,例如辣根猿叶甲的幼虫,菜蛾,黑尾叶蝉的毛虫,草地夜蛾或桃叶蚜。
活性化合物可以加工成常规的剂型,例如溶液,乳剂,可湿性粉剂,悬浮剂,粉剂,糊剂,可溶性粉剂,颗粒剂,悬浮浓乳剂,浸有活性化合物的天然和合成材料,以及在聚合物质中的微胶囊。
这些剂型按照已知的方法生产,例如通过混合活性化合物与扩展剂,即液体溶剂和/或固体载体,可选择使用表面活性剂,即乳化剂和/或分散剂,和/或发泡剂。
在水作扩展剂的情况下,例如有机溶剂也可用作助溶剂。作为液体溶剂,适合的主要有:芳烃,例如二甲苯,甲苯或烷基萘,氯代芳烃或氯代脂肪烃,例如氯苯,二氯乙烷或二氯甲烷,脂肪烃,例如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,醇类,例如丁醇或乙二醇以及它们的醚或酯,酮类,例如丙酮,甲乙酮,甲基异丁基酮或环己酮,强极性溶剂,例如二甲基甲酰胺和二甲基亚砜,以及水。
作为固体载体适宜的有:例如铵盐和磨碎的天然矿物,例如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱石或硅藻土,以及磨碎的合成矿物,例如高分散性二氧化硅,氧化铝和硅酸盐;作为颗粒剂的固体载体适合的有:例如压碎和分级的岩石例如方解石,大理石,浮石,海泡石和白云石,以及合成的无机和有机粉的颗粒,和有机材料颗粒例如锯末,可可壳,玉米芯和烟草茎的颗粒;作为乳化剂和/或发泡剂适合的有:例如非离子和阴离子乳化剂,如聚乙撑脂肪酸酯,聚氧乙撑脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,硫酸烷基酯,芳基磺酸盐以及蛋白的水解产品;作为分散剂适合的有:例如木质素亚硫酸盐废液和甲基纤维素。
粘合剂例如羧甲基纤维素和粉末、颗粒或乳汁形式的天然和合成的聚合物,例如***胶,聚乙烯醇和聚乙烯乙酸酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成的磷脂,都可在剂型中应用。其它添加剂是矿物油和植物油。
也可使用着色剂例如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,和有机染料,例如茜素染料,偶氮染料和金属酞菁染料,和微量营养素例如铁、锰、硼、铜、钴、钼和锌盐。
这些剂型一般含有以重量计0.1~95%的活性化合物,优选0.5~90%。
本发明的活性化合物可以它的市售剂型的形式存在以及从这些剂型制备的,作为与其它活性化合物的混合物的使用形式存在,其它活性化合物例如杀虫剂,诱引剂,不育剂,杀细菌剂,杀螨剂、杀线虫剂,杀真菌剂,生长调节物质或除草剂。杀虫剂包括,例如,磷酸酯类,氨基甲酸酯类,羧酸酯类,氯代烃类,苯基脲类,由微生物产生的物质等等。
特别适合的混合组分如下,例如:
杀菌剂:2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-酰替苯胺;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚胺基N-甲基-2-(2-苯氧苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧亚胺基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基酚(OPP),aldimorph,氨丙膦酸,敌菌灵,戊环唑,苛霜灵,麦锈灵,苯菌灵,乐杀螨,联苯,双苯***醇,灭瘟素,糠菌唑,磺嘧菌灵,粉病定,
多硫化钙,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌清,乙菌利,硫杂灵,霜脲氰,环唑醇,酯菌胺,
双氯酚,苄氯***醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,甲菌定,烯酰吗啉,烯唑醇,敌螨普,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,敌菌酮,克瘟散,氧唑菌,乙菌定,氯唑灵,
异嘧菌醇,腈苯唑,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,薯瘟锡,毒菌锡,福美铁,嘧菌腙,氟啶胺,氟噁菌,氟菌安,喹唑菌酮,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋氨丙灵,拌种胺,
双胍盐,
六氯苯,己唑醇,土菌消,
烯菌灵,酰胺唑,双胍辛醋酸盐,异稻瘟净,异丙定,稻瘟灵,春雷霉素,铜制剂例如:氢氧化铜,环烷酸铜,王铜,硫酸铜,氧化铜,喹啉铜和波尔多液,锰铜混剂,代森锰锌,代森锰,嘧菌胺,丙氧灭锈胺,甲霜灵,环戊唑菌,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,
福美镍,异丙消,环菌灵,
甲呋酰胺,噁霜灵,oxamocarb,氧化萎锈灵,
稻瘟酯,戊菌唑,戊菌隆,双氯苯磷,四氯苯酞,多马霉素,粉病灵,福代锌,多氧霉素,烯丙异噻唑,味鲜安,腐霉利,霜霉威,丙环唑,甲基代森锌,定菌磷,啶斑肟,二甲嘧菌胺,咯喹酮,
五氯硝基苯,
硫黄粉和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,氟醚唑,涕必灵,噻菌清,甲基托布津,福美双,甲基立枯磷,对甲抑菌灵,***酮,***醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,戊叉唑菌,
井冈霉素,烯菌酮,
代森锌,福美锌。
杀细菌剂:
溴硝丙二醇,双氯酚,氯定,福美镍,春雷霉素,异噻菌酮,呋喃羧酸,土霉素,烯丙异噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素,氟唑虫清,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,虫螨脒,齐墩螨素,AZ 60541,艾扎丁,azinphos A,谷硫磷(azinphos M),唑环锡,苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,β-氟氯氰菊酯,氟氯菊酯,丁苯威,brofenprox,溴硫磷(bromophos A),合杀威,噻嗪酮,丁叉威,丁基哒螨酮(butylpyridaben),硫线磷,甲萘威,克百威,三硫磷,丁硫克百威,杀螟丹,氟啶蜱脲,氟丙氧脲,除线威(chloethocarb),壤虫氯磷,毒虫畏,定虫隆,氯甲磷,毒死蜱,甲基毒死蜱,顺灭虫菊(cis-resmethrin),clocythrin,四螨嗪,杀螟腈,乙氰菊酯,氟氯氰菊酯,(RS)氯氟氰菊酯,三环锡,氯氰菊酯,灭蝇胺,溴氰菊酯,(demeton M),一○五九,甲基一○五九,杀螨隆,二嗪农,除线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌杀磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,苯虫威,乙硫磷,醚菊酯,灭克磷,氧嘧啶磷,
克线磷,喹螨醚,杀螨锡,杀螟松,丁苯威,苯硫威,双氧威,甲氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,锐劲特,氟啶胺,氟螨脲,氟氰戊菊酯,氟虫脲,氟丙苄醚,氟胺氰菊酯,地虫磷,安果,噻唑酮磷,fubfenprox,呋线威,
林丹,庚虫磷,氟铃脲,嘧螨酮,
吡虫啉,异稻瘟净,氯唑磷,丙胺磷,异丙威,异噁唑磷,齐墩螨素(ivermectin),氯氟氰菊酯,氟丙氧脲,
马拉硫磷,灭蚜磷,速灭磷,甲亚砜磷,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭虫威,灭多威,速灭威,米尔螨素,久效磷,moxidectm,
二溴磷,NC 184,吡虫清,硝胺烯啶,
氧化乐果,甲氨叉威,oxydemethon M(译者:可能是砜吸磷oxydemeton),异砜磷,
对硫磷(parathion A),甲基对硫磷,氯菊酯,稻丰散,甲拌磷,伏杀磷,亚胺硫磷,磷胺,辛硫磷,抗蚜威,虫螨磷(pirimiphos M),pirimiphos A,丙溴磷,猛杀威,丙虫磷,残杀威,发果,拒嗪酮,吡唑硫磷(pyrachlophos),pyradaphenthion,烯苄呋菊酯,除虫菊,哒螨酮,嘧胺苯醚,蚊蝇醚,喹硫磷,
双苯酰肼,
蔬果磷,硫线磷,灭虫硅醚,硫特普,乙丙硫磷,
双苯酰肼,吡螨胺,嘧丙磷,伏虫隆,七氟菊酯,双硫磷,叔丁威,特丁磷,杀虫畏,thiafenox,硫双灭多威,特氨叉威,甲基乙拌磷,硫磷嗪,敌贝特,四溴菊酯,苯赛螨,***磷,triazuron,敌百虫,杀虫隆,混灭威,
蚜灭多,二甲威,灭杀成,YI 5301/5302,zetamethrin。
也可以与其它已知的活性化合物,例如除草剂,或与化肥和生长调节剂组成混合物。
而且本发明的活性化合物可以作为与增效剂的混合物存在于它们的市售制剂中和由这些制剂配成的使用形式中。增效剂是能够提高活性化合物活性的化合物,所加增效剂本身不必是活性化合物。
从市售制剂配成的使用形式中的有效成分含量可在宽限范围内变化。使用形式中活性化合物的浓度可以是以重量计的0.0000001~95%,优选0.0001和1%。
这些化合物以适合于使用药剂的常规方法施用。
当用于防治卫生害虫和贮存产品的害虫时,要通过在木材和粘土上的显著残留作用和对石灰基质上的碱的良好稳定性来鉴别活性化合物。
本发明的活性化合物不仅可以防治植物害虫,卫生害虫和贮存产品的害虫,而且可以防治畜牧方面的动物寄生虫,例如硬蜱,软蜱,疥螨,恙螨,蝇(叮咬的和舔吃的),寄生蝇幼虫,虱,头虱,羽虱和蚤。这些寄生虫包括:
虱目,例如血虱属,颚虱属,虱属,阴虱属和管虱属。
食毛目和粗颈豆象亚目与细角亚目,例如毛羽虱属,短角鸟虱属,巨羽虱属,牛羽虱属,Werneckiella spp,Lepikentron spp,畜虱,嚼虱属和猫羽虱属。
双翅目和长角亚目与细角亚目,例如伊蚊属,按蚊属,库蚊属,蚋属,真蚋属,白蛉属,Lutzomyia spp,库蠓属,斑虻属,Hybromitra spp,黄虻属,虻属,麻虻属,Philipomyia spp,蜂虱蝇属,家蝇属,齿股蝇属,螯蝇属,角蝇属,莫蝇属,厕蝇属,舌蝇属,丽蝇属,绿蝇属,金蝇属,污蝇属,麻蝇属,狂蝇属,皮蝇属,胃蝇属,虱蝇属,羊虱蝇属和蜱蝇属。
蚤目,例如蚤属,栉首蚤属,印鼠客蚤和角叶蚤属。
半翅目,例如臭虫属,椎猎蝽属,长红猎蝽和全圆蝽属。
蜚蠊目,例如东方蜚蠊,美洲大蠊,德国小蠊和棕带蠊。
粉螨亚纲和窨蛛目与中气门亚目,例如锐缘蜱属,纯缘蜱属,残喙蜱属,橙粉蝶属,花蜱属,牛蜱属,革蜱属,Haemophysalis spp,璃眼蜱属,扇头蜱属,皮刺螨属,刺利螨属,肺刺螨属,胸孔螨属和瓦螨属。
辐螨亚目和粉螨目,例如,蜂跗线螨属,姬螯螨属,禽螯厘螨属,肉螨属,疮螨属,蠕形螨属,恙螨属,牦螨属,粉螨属,食酪螨属,嗜木螨属,颈下螨属,翅螨属,瘙螨属,痒螨属,耳螨属,疥螨属,痂螨属,疙螨属,胞螨属和皮膜螨属。
通式(Ⅰ)的本发明活性化合物也适用于防治侵害农业生产的家畜、爱畜和所谓的试验动物的节肢动物,家畜例如牛,羊,山羊,马,猪,驴,骆驼,水牛,兔,鸡,火鸡,鸭,鹅和蜜蜂,爱畜例如狗,猫,笼中鸟和养鱼缸的鱼,试验动物例如仓鼠,豚鼠,大鼠和小鼠。通过防治这些节肢动物,可以减少死亡和生产率的下降(关于肉,奶,毛,兽皮,蛋,蜂蜜等),因此通过本发明化合物的使用使更经济和更省力的畜牧业成为可能。
本发明的活性化合物还可通过各种给药方式以已知的方法用于兽医方面,通过内部给药的方式,例如片剂,胶囊剂,药水,灌药,颗粒剂、糊剂,boli,通过饲料和栓剂,通过非肠道的给药方式,例如注射(肌内注射,皮下注射,静脉注射,腹膜内注射等),植入,通过鼻子施药的方式,通过皮肤施药的方式,例如浸泡或淋浴,喷洒,拨浇和沾药,洗涤和喷粉,也可以借助于含活性化合物的成模品,例如项圈,耳坠,尾坠,肢带,缰绳,标记器件等。
当用于家畜,家禽,爱畜等时,通式(Ⅰ)的活性化合物以制剂的形式直接使用(例如粉剂,乳剂,自由流动的混合物),或稀释100~10000倍后使用,或作为化学浴使用,制剂中活性化合物的含量为以重量计1~80%。
而且已经发现本发明的通式(Ⅰ)化合物对于毁坏工业材料的昆虫具有有效的杀虫活性。
以下昆虫可以作为实例和作优选但并不限于此:
鞘翅目,例如
北美家天牛,黄虎天牛,家具切蠹,极死材窃蠹,梳角细脉切蠹,Dendrobium pertinex,松芽枝窃蠹,Priobium carpini,褐粉蠹,美洲粉蠹,南方粉蠹,栎粉蠹,柔毛粉蠹,粉蠹(Trogoxylon aequale),鳞毛粉蠹,材小蠹属,棘胫小蠹,咖啡黑长蠹,槲长蠹(Bostrychuscapucins),褐异翅长蠹,长蠹属和竹竿粉长蠹。
膜翅目,例如
蓝黑树蜂,云杉大树蜂,泰加大树蜂和Urocerus augur。
等翅目,例如
木白蚊(Kalotermes flavicollis),麻头堆沙白蚊,印巴结构木异白蚊,欧美散白蚊,Reticulitermes santonensis,Reticulitermes lucifugus,达尔文澳白蚊,内华达古白蚊,台湾乳白蚊。
缨尾目,例如衣鱼。
在本文中工业材料被理解为非生命物质,例如,优选塑料、粘合剂、胶料、纸和纸板,皮革,木材和木材加工产品以及涂料。
特别优选的可防止害虫侵害的材料是木材和木材加工产品。
可用本发明的药剂或含此药剂的混合物防护的木材及木材加工产品可理解为,例如:建筑的栋木,木制的横梁,枕木,桥梁的部件,船码头,木制车辆,板条箱,制模板,容器,电线杆,木制操作盘,木制门窗,胶合板,木屑板,在房屋建筑或建筑的细木工技术中一般使用的细木工所制产品或木制产品。
活性化合物可以浓制剂的形式或一般常用的剂型,如粉剂,颗粒剂,溶液,悬浮剂,乳剂或糊剂的形式来使用。
所说的剂型可通过本来已知的方法来制备,例如将活性化合物与至少一种溶剂或稀释剂,乳化剂,分散剂和/或粘合剂或固定剂,防水剂,如果适合的话催干剂和紫外光稳定剂和如果适合的话染料和颜料,以及其它加工助剂相混合。
用于保护木材和木制的栋木产品的杀虫组合物或浓制剂所含的本发明活性化合物的浓度为以重量计0.0001~95%,特别是0.001~60%。
所使用的组合物或浓制剂的量取决于害虫的性质和出现情况以及介质。最佳使用量各自通过一系列试验来确定。可是一般,基于被防护的材料,使用以重量计的活性化合物0.0001~20%,优选0.001~10%就足够了。
所用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性的或类油的有机化学溶剂或溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水和如果适合的话乳化剂和/或湿润剂。
优选使用的有机化学溶剂是油性的或类油的溶剂,其蒸发值高于35,闪点高于30℃,优选高于45℃。
相应的矿物油或芳烃馏份或含矿物油的溶剂混合物,优选试验汽油,石油和/或烷基苯可用作非水溶性的,油性和类油的低挥发性溶剂。
沸程为170~220℃的矿物油,沸程为170~220℃的试验挥发油,沸程为250~350℃的锭子油,沸程为160~280℃的石油或芳烃,terpentine油等优先被选用。
在优选方案中,采用沸程为180~210℃的液态脂肪烃或沸程为180~220℃的芳香和脂肪烃的高沸混合物和/或锭子油和/或一氯萘,优选α-一氯萘。
低挥发性并具有蒸发值高于35和闪点高于30℃,优选高于45℃的有机油性或类油溶剂可以部分地被高或中等挥发性的有机化学溶剂所取代,这些溶剂提供的溶剂混合物具有蒸发值35以上,闪点30℃以上,优选45℃以上,并且可将杀虫剂/杀菌剂混合物溶解在其中,或乳化在其中。
根据优选的方案,一些有机化学溶剂或溶剂混合物或脂族极性有机化学溶剂或溶剂混合物可被替代。含有羟基和/或酯基和/或醚基的脂族有机化学溶剂,例如乙二醇醚,酯等等优先被采用。
在本发明中采用的有机化学粘合剂是可用水稀释的和/或在所用已知有机溶剂中可溶解的或可分散的或可乳化的合成树脂和/或粘结的干性油特别是含有以下组成的粘合剂:丙烯酸树脂,乙烯树脂,例如聚醋酸乙烯酯,聚酯树脂,缩聚或加聚树脂,聚氨酯树脂,醇酸树脂或改性醇酸树脂,酚醛树脂,烃树脂,例如茚-苯并呋喃树脂,硅氧烷树脂,干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干燥粘合剂。
用作粘合剂的合成树脂可以乳液,分散液或溶剂形式被应用。沥青或沥青材料也可用作粘合剂,用量以重量计可达10%。此外,已知的染料,颜料,防水剂,去味剂和抑制剂或抗腐蚀剂等也可被采用。
根据本发明,组合物或浓制剂至少优选含有一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。根据本发明,优选采用以重量计油含量高于45%,优选50~68%的醇酸树脂。
所述的全部或一些粘合剂可被固化剂(混合物)或增塑剂(混合物)代替。这些添加剂是要防止活性化合物的蒸发和结晶或沉淀。优选替代粘合剂的0.01~30%(基于100%的所用粘合剂)。
增塑剂来源于邻苯二甲酸酯类,例如邻苯二甲酸二丁酯,二辛酯或苄基丁基酯,磷酸酯类,例如磷酸三丁酯,己二酸酯类,例如二(2-乙基己基)己二酸酯,硬脂酸酯类,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯类,例如油酸丁酯,丙三醇醚或较高分子量的乙二醇醚,丙三醇酯和对甲苯磺酸酯。
固定剂化学组成基于聚乙烯基烷基醚,例如聚乙烯基甲基醚,或酮类,例如二苯甲酮或乙撑二苯甲酮。
可能的溶剂或稀释剂,特别是水,如果适合的话可混合一种或多种上述的有机化学溶剂或稀释剂,乳化剂和分散剂。
特别有效的木材防护可以通过大工业规模的浸渍方法,例如真空,双重真空或加压方法来完成。
预先制好的组合物,如果适合,也可含有其它杀虫剂,和如果合适,也可含有一种或多种杀菌剂。
优选可能添加的混合组分是在WO 94/29 268中所述的杀虫剂和杀菌剂。在该文件中所说的化合物是本申请的明确的组成部分。
特别优选的混合组分是杀虫剂,例如毒死蜱,辛硫磷,蔬果磷,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,吡虫清,氟虫脲,氟铃脲,杀虫隆,以及杀菌剂,例如氧唑菌,戊唑醇,环唑醇,环戊唑菌,烯菌灵,diclofluanid,对甲抑菌灵,3-碘-2-丙炔基-丁基氨基甲酸酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基-异噻唑啉-3-酮。
从以下实施例可见本发明活性化合物的制备与应用。
制备实施例
实施例1
将2.52克(0.01摩尔)3H-1-(2-氯吡啶-5-基)-2-硝基亚胺基咪唑啉和0.24克(0.01摩尔)氢氧化锂溶解于30毫升水中并在室温将该溶液搅拌片刻。过滤反应溶液并将滤液真空浓缩。残留物在五氧化磷上真空干燥。
得到2.43克(理论量的93%)3H-1-(2-氯吡啶-5-基)-2-硝基亚胺基咪唑啉的锂盐。
MS谱(通过FAB法)*:MH+=260。
[FAB:快速原子撞击]
类似地或是按照制备的一般指示制得了以下通式(Ⅰ)化合物:
应用实施例
从EP-A 0 315 826已知的化合物(A)1-(2-氯吡啶-5-基)-3-甲基-2-硝基亚胺基咪唑啉
实施例A
猿叶甲幼虫试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷基芳基聚乙二醇醚
为了产生一种适合的活性化合物的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该浓制剂用水稀释至所需浓度。
将甘蓝叶在所需浓度的活性化合物制剂中浸渍过,然后引入辣根猿叶甲幼虫,叶片一直保持湿润。
经过特定时间后,测定消灭的%。100%表示甲虫幼虫全部被杀死;0%表示没有甲虫幼虫被杀死。
在本试验中,活性化合物的浓度,例如0.01%时,各自在用药后7天,制备实施例1的化合物可消灭90%和制备实施例2,3,4和5的化合物可消灭100%,而已知的化合物(A)仅消灭10%甲虫幼虫。
实施例B
菜蛾试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷基芳基聚乙二醇醚
为了产生一种适合的活性化合物制剂,将1份重量的活性化合物与所说明量的溶剂与乳化剂相混合,并将该浓制剂用水稀释至所需浓度。
将甘蓝叶在所需浓度的活性化合物制剂中浸渍过,再引入小菜蛾的毛虫,而叶子一直保持湿润。
经过特定时间后,测定消灭的%。100%表示毛虫全部被杀死;0%表示没有毛虫被杀死。
在本试验中,活性化合物的浓度,例如为0.1%时,各自在用药7天后,例如制备实施例2,3,4和5化合物消灭100%和制备实施例6的化合物消灭85%,而已知的化合物(A)仅消灭25%的毛虫。
实施例C
夜蛾试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷基芳基聚乙二醇醚
为了产生一种合适的活性化合物制剂,将1份重量的活性化合物与所说明量的溶剂和乳化剂相混合,并用水将浓制剂稀释至所需浓度。
将甘蓝叶在所需浓度的活性化合物制剂中浸渍过,然后引入夜蛾毛虫,叶子一直保持湿润。
经过特定时间后,测定消灭%。100%表示毛虫全部被杀死;0%表示毛虫没有被杀死。
在本试验中,在活性化合物浓度,例如为0.1%时,用药后7天,制备实施例1,2,3,4,5和6的化合物消灭100%,而已知的化合物(A)仅消灭50%的毛虫。
实施例D
黑尾叶蝉试验
溶剂:7份重量的二甲基甲酰胺
乳化剂:1份重量的烷基芳基聚乙二醇醚
为了产生一种合适的活性化合物制剂,将1份重量的活性化合物与所说明量的溶剂和乳化剂相混合,然后用水将浓制剂稀释至所需浓度。
将稻苗在所需浓度的活性化合物制剂中浸渍过,并引入黑尾叶蝉幼虫,稻苗一直保持湿润。
经过特定时间后,测定消灭的%。100%表示所有的幼虫被杀死;0%表示没有幼虫被杀死。
在本试验中,活性化合物的浓度,例如为0.001%时,用药后6天,例如制备实施例1,2,3,4,5和6的化合物消灭100%,而已知的化合物(A)仅消灭50%幼虫。
实施例E
桃蚜-合成双膜试验(sachet test)
溶剂:水,取决于溶解度,丙酮
将每个活性化合物制备成在适当溶剂中的0.1%常备溶液。用15%蔗糖水的溶液把常备溶液稀释至适当的试验浓度。
将特定的活性化合物溶液吸移到石蜡(parafilm)的合成双膜上。再把双膜罩到放有15只桃蚜成虫的容器上。在本试验方法中,蚜虫口服活性化合物。
经过特定时间后,测定在各种浓度下以百分比计的灭虫数。通过probit分析计算LC50值。LC50值表示杀死50%所用动物的浓度。LC50值越低,制剂的活性越高。
在本试验中,用药后2天,制备实施例1,2,3,4,5和6的化合物的LC50值在0.006~0.048ppm之间,而已知的化合物(A)LC50值为0.15。
表E(危害植物的害虫)桃蚜-合成双膜试验
Claims (7)
3.防治害物的组合物,其特征在于它们至少含有一种根据权利要求1的通式(Ⅰ)的咪唑啉衍生物的盐。
4.根据权利要求1的通式(Ⅰ)的咪唑啉衍生物的盐在防治害物上的应用。
5.防治害物的方法,其特征在于允许根据权利要求1的通式(Ⅰ)的咪唑啉衍生物的盐作用于害物和/或其环境中。
6.用于防治害物的组合物的制备方法,其特征在于将根据权利要求1的通式(Ⅰ)的咪唑啉衍生物的盐与扩展剂和/或表面活性剂相混合。
7.根据权利要求1的通式(Ⅰ)的咪唑啉衍生物的盐在制备防治害物的组合物中的应用。
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US20050118164A1 (en) * | 2001-03-09 | 2005-06-02 | William Herman | Targeted ligands |
US20050142539A1 (en) * | 2002-01-14 | 2005-06-30 | William Herman | Targeted ligands |
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