CN1241996A - 氟代丁烯酰基肼类化合物 - Google Patents
氟代丁烯酰基肼类化合物 Download PDFInfo
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- CN1241996A CN1241996A CN 96197374 CN96197374A CN1241996A CN 1241996 A CN1241996 A CN 1241996A CN 96197374 CN96197374 CN 96197374 CN 96197374 A CN96197374 A CN 96197374A CN 1241996 A CN1241996 A CN 1241996A
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- alkyl
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Landscapes
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Abstract
本发明涉及新颖的式(Ⅰ)氟代丁烯酰基肼类化合物、其制备方法及其防治动物害虫的应用,其中Y代表C=O、C=S或SO2,R1代表氢或卤素,且R2代表烷基、卤代烷基、烷氧基烷基、烷硫基烷基、环烷基、链烯基、链烯氧基、烷氧基、环烷基氧基、烷硫基或各任选取代的芳基、芳烷基、芳烷氧基或杂芳基。
Description
本发明涉及新颖的氟代丁烯酰基肼类化合物、其制备方法及其防治动物害虫,特别是在农业、森林、贮藏产品和材料保护和卫生方面遇到的昆虫、蜱螨和线虫的应用。
业已知道,某些氟代链烯基化合物具有杀虫、杀螨和杀线虫活性(参见,例如WO 92/15 555,US-4 952 580、US-4 950 666、US-3 914251)。然而,这些化合物的活性和作用谱,特别是在低施用量和浓度下,并不总是令人完全满意的。
因此,本发明提供新颖的式(I)氟代丁烯酰基肼其中Y 代表C=O、C=S或SO2,R1 代表氢或卤素,且R2 代表烷基、卤代烷基、烷氧基烷基、烷硫基烷基、环烷基、链烯基、链烯氧基、烷氧基、环烷基氧基、烷硫基或各任选取代的芳基、芳烷基、芳烷氧基或杂芳基。
根据取代基的性质,式(I)化合物可以以几何和/或光学异构体或不同组成的异构体的混合物存在。本发明既涉及纯异构体,也涉及异构体混合物。
再则,业已发现,可以如下获得式(I)的氟代丁烯酰基肼。A)使式(II)的酰肼与式(III)酰基氯反应
R2-Y-NH-NH2 (II)
其中
R2和Y各如上所定义,
其中
R1 如上所定义,
其中
R1 如上所定义
R2-Y-Cl (V)
其中
R2和Y 如上所定义,
如果需要,反应在稀释剂或碱存在进行。
最后,业已发现,新颖的式(I)氟代丁烯酰基肼具有非常显著的生物性能,且特别适合用于防治动物害虫,特别是在农业、森林、贮藏产品和材料保护和卫生方面中遇到的昆虫、蜱螨和线虫。
式(I)提供本发明氟代丁烯酰基肼的一般定义。
在上下文中提到化学式中列出的基团的优选取代基或范围说明如下:Y 优选代表C=O、C=S或SO2。R1 优选代表氢、氟、氯或溴。R2 优选代表C1-C8-烷基、C1-C8-卤代烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷硫基-C1-C6-烷基、C3-C10-环烷基、C2-C8-链烯基、C2-C8-链烯氧基、C1-C20-烷氧基、C3-C10-环烷基氧基、C1-C20-烷硫基、各自任选由卤素-、硝基-、氰基-、氨基-、羟基-、C1-C6-烷基-、C1-C6-烷氧基-或C1-C6-烷硫基取代的苯基、苯基-C1-C4-烷基或苯基-C1-C4-烷氧基或任选由卤素-或C1-C6-烷基取代的5-或6-元杂芳基,该杂芳基具有一或二个选自氧、硫和氮的杂原子。Y 特别优选代表C=O、C=S或SO2。R1 特别优选代表氢或氟。R2 特别优选代表C1-C6-烷基、C3-C6-环烷基、C3-C8-链烯基、C3-C8-链烯氧基、C1-C6-烷氧基、C3-C6-环烷基氧基、C1-C6-烷硫基、各自任选由氟-、氯-、溴-、羟基-、C1-C4-烷基-或C1-C4-烷氧基取代的苯基、苯基-C1-C2-烷基或苯基-C1-C2-烷氧基或各自任选由C1-C4-烷基取代的呋喃基、噻吩基或吡啶基。
上面提到的一般或优选的基团定义或说明适合于终产物,且相应地适合于起始原料和中间体。这些基团的定义可以按需要相互组合,即,包括分别优选的范围间的任意组合。
本发明优选的式(I)化合物含有上面作为优选的含义给出的定义的组合。
本发明特别优选的式(I)化合物含有上面作为特别优选的含义给出的定义的组合。
在上下文给出的基团定义中,烃基如烷基或链烯基——即,包括在与杂原子的组合如烷氧基或烷硫基中——在可能的情况下是直链或支链的。
根据方法A),使用例如3,4,4-三氟丁-3-烯酰基氯和肼基甲酸乙酯作为起始原料制备式(I)化合物时,反应的途径可以用下列反应式来代表:
上面描述的制备式(I)化合物的方法A)的特征在于,使式(II)的酰肼与式(III)的酰基氯反应,如果需要,反应在稀释剂或碱存在下进行。
本发明方法A)优选在稀释剂存在下进行。
适合的稀释剂特别是有机溶剂,例如任选氯代的脂族或芳族烃如环己烷、甲苯、二甲基、二氯甲烷、二氯乙烷、氯仿或氯苯,醚类如乙醚、二噁烷或四氢呋喃,腈类如乙腈,亚砜类如二甲基亚砜或酰胺类如二甲基甲酰胺。
适合的稀释剂也可以是由水和有机溶剂组成的二相体系,例如水/二氯甲烷或水/甲苯。
适合使用的碱原则上是所有的适合于这种酰化反应的有机或无机碱。
优选的是胺,特别是叔胺如三乙胺、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、二氮杂二环辛烷(DABCO)或吡啶或碱金属或碱土金属碳酸盐、碳酸氢盐或氢氧化物。实例包括碳酸钠、碳酸钾、碳酸氢钠、氢氧化钠、氢氧化钾和氢氧化钙。
方法A)中的反应温度可以在相对宽的范围内变化。通常,反应是在-10℃至160℃间,优选在0℃至100℃间的温度下进行。
式(II)化合物与式(III)化合物的摩尔比通常是3∶1至1∶3,优选1.5∶1至1∶1.5。
反应通常是在常压下进行的。
后处理时,将反应混合物例如水解,并将产物用有机溶剂如乙酸乙酯、二氯甲烷或甲苯萃取。在去除溶剂后,粗产物可以任选通过重结晶或色谱来纯化。
上面描述的制备式(I)化合物的方法B)的特征在于,使式(IV)的酰基肼与式(V)的酰基氯反应,如果需要,反应在稀释剂或碱存在下进行。
适合用于此方法的稀释剂是上面方法A)中提到的所有溶剂或二相体系。
适合用于此方法的碱是上面方法A)中提到的所有的碱。
方法B)中的反应温度可以在相对宽的范围内变化。通常,反应是在-10℃至160℃间,优选在0℃至100℃间的温度下进行。
式(IV)化合物与式(V)化合物的摩尔比通常是3∶1至1∶3,优选1.5∶1至1∶1.5。
反应通常是在常压下进行的。
反应混合物可以通过例如上面描述的用于方法A)的方法来后处理。
制备方法A)需要的起始原料式(II)酰肼是已知的和/或可以用已知的方法通过简单的方式制备。
式(II)的酰肼是例如通过式(V)的酰基氯与肼反应而获得的。
制备方法A)需要的起始原料式(III)酰基氯是已知的(参见,例如US-5 389 680和EP-432 861)。
制备方法B)需要的起始原料酰基肼可以通过使式(III)酰基氯与肼反应而简单地制备。
式(V)的酰基氯是有机化学一般已知的化合物。
本发明活性化合物适合用于防治动物害虫,特别是在农业、森林、贮藏产品和材料保护以及卫生方面上遇到的昆虫、蜱螨和线虫。它们可以优选用作作物保护剂。它们对正常敏感和抗性种类和对所有或单个的生长发育阶段有活性。上述害虫包括:等足纲,例如,潮虫(Oniscus asellus)、平甲虫(Armadillidium vulgare)和斑鼠妇(Porcellio scaber)。倍足纲,例如,具斑马陆(Blaniulus guttulatus)。唇足纲,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigeraspec)。综合纲,例如,庭院幺蚰(Scutigerella immaculata)。缨尾目,例如,西洋衣鱼(Lepisma saccharina)。弹尾目,例如,具棘跳虫(Onychiurus armatus)。直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattellagermanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoria migratorioids)、殊种蚱蜢(Melanoplusdifferentialis)和沙漠蝗(Schistocerca gregaria)。革翅目,例如,欧洲球螋(Forficula auricularia)。等翅目,例如,犀白蚁属(Reticulitermes spp.)。虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalineaspp.)。缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thripstabaci)。半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatomaspp.)。同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisiatabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphisgossypii)、甘蓝蚜(Brevicoryne brassicae)、茶 隐瘤蚜(Cryptomyzusribis)、甜菜蚜(Aphis fabae)、苹果蚜(Doralis pomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterus arundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodonhumili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoascaspp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettixcincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetiaoleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvatalugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupaluspiniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletisblancardella)、苹果巢蛾(Hyponomeuta padella)、小菜蛾(Plutellamaculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotisspp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodoptera exigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pierisspp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineola bisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoecia podana)、织网衣蛾(Capua reticulana)、云松卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、Bruchidius obtectus、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsa decemlineata)、辣根猿叶甲(Phaedoncochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodeschrysocephala)、墨西哥豆甲(Epilachna varivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hyperapostica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctusspp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptus hololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Tribolium spp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotesspp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampa spp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespaspp.)。双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Muscaspp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebraspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibiohortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllusspp.)。蛛形纲,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectus mactans)。蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodesspp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobiapraetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychusspp.)。
植物寄生线虫包括例如垫刃线虫(Pratylenchus spp.)、毕肖穿孔线虫(Radopholus similis)、Ditylenchus dipsaci、Tylenchulussemipenetrana、异皮线虫(Heterodera spp.)、囊线虫(Globoderaspp.)、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelechoides spp.)、Longidorus spp.、剑线虫(Xiphinema spp.)和髦根线虫(Trichodorusspp.)。
本发明式(I)活性化合物具有特别突出的杀线虫活性,例如,杀黄麻根结线虫(Meloidogyne incognita)的活性。
它们具有内吸作用,且可以经叶片施用。
它们具有良好的杀虫活性。
本活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、水溶性粉剂、颗粒剂、悬浮乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微胶囊。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂,即液体溶剂和/或与固体载体混合,需要时使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作填充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份、矿物油和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合固体载体是:例如压碎并分级的天然岩石如方解石、大理石、浮石、海泡石和白云石,以及无机和有机粉的合成颗粒,和如下有机材料的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的添加物可以是矿物油和植物油。
也可能使用着色剂,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
本发明活性化合物可以其商业上可行的制剂和由这些制剂制备的使用形式存在,所述的制剂为与如下的其它活性化合物的混合物:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂包括例如磷酸酯类、氨基甲酸酯、羧酸酯类、氯代烃类、苯基脲类和由微生物生产的物质等。
在混合物的特别有利的组分是例如下列:杀真菌剂:
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-甲酰苯胺;2,6-二氯-N-(4-三氟甲基苯甲基)苯甲酰胺;(E)-2-甲氧基亚氨基-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-氧基]苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚氨基[α-(邻甲苯氧基)-邻甲苯基]乙酸甲酯;2-苯基苯酚(OPP)、aldimorph、氨丙磷酸、敌菌灵、戊环唑、苯霜灵、碘萎灵,苯菌灵、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、酯菌胺、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克菌散、环氧唑(epoxyconazole)、乙嘧啶、氯唑灵、双氯苯嘧啶、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、fludioxonil、氟氯菌核利、fluquinconazole、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、四氯苯酞、麦穗宁、呋霜灵、拌种胺、双胍辛、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛醋酸盐、异稻瘟净、异菌脲、稻瘟灵、春日霉素、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、噻菌胺、腈菌唑、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、氧化萎锈灵、perfurazoat、戊菌唑、戊菌隆、稻病磷、四氯苯酞、匹马菌素、哌啶宁、plycarbamate、多氧霉素、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、五氯硝基苯、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、氟醚唑、噻菌灵、噻菌腈、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核利、代森锌、福美锌。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素、AC 303 630、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维菌素(avermectin)、AZ 60541、azadirachtin、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮,硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、CGA 157 419、CGA 184699、除线威、chlorethoxyfos、毒虫畏、定虫隆、氯甲硫磷、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷II、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、锐劲特(fipronil)、氟啶胺、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚烯磷、氟铃脲、噻螨酮、吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、NI 25、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、pyrachlophos、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、RH 5992、水杨硫磷、硫线磷、silafluofen、治螟磷、甲丙硫磷、tebufenozide、tebufenpyrad、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、YI 5301/5302、zetamethrin。
也可以是与其它已知活性化合物如除草剂或与化肥和生长调节剂的混合物。
此外,本发明活性化合物可以以其商业上可行的制剂和以由这些制剂制备的使用形式存在。这些制剂可以是与增效剂的混合物。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
使用形式是以适合的常规形式采用的。
当防治卫生和贮藏产品方面的害虫时,活性化合物的突出之处在于其在木材和陶土上的显著残留作用和对石灰处理过的底物上的碱的良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、隐喙蜱科、疥螨、恙螨科、(叮咬和吸吮)蝇、寄生蝇幼虫、毛虱、鸟虱和蚤有活性。这些寄生虫包括:虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)和阴虱属(Phthirus spp.)、盲虱属(Solenoptes spp.)。食毛目及amblycerina和lschnocerina亚目,例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、Trinoton spp.、羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodecte spp.)和Felicolaspp.。双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyiaspp.)、库蚊属(Culicoides spp.)、斑虻属(Chrysops spp.)、Hybomitraspp.、Atylotus spp.、虻属(Tabanus spp.)、麻虻属(Haematopotaspp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、Hydrotaea spp.、螫蝇属(Stomoxys spp.)、血蝇属(Haematobiaspp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophagaspp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、Lipoptena spp.和羊虱蝇属(Melophagus spp.)。蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalides spp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllus spp.)。半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Phodnius spp.)和全圆蝽属(Panstrongylus spp.)。蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplanetaamericana)、德国小蠊(Blattela germanica)和Suppella spp.。蜱螨亚纲及后气目(Metastigmata)和中气目(mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、Otabius spp.、硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilusspp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、Raillietia spp.、肺刺螨属(Pneumonyssusspp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。Actinedida(前气孔亚目)和Acaridida(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、绵羊疥螨属(Psorergates spp.)、脂螨属(Iemodex spp.)、恙螨属(Trombiculaspp.)、嫠螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、Hypodectesspp.、翼衣属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、Otodectes spp.、疥螨属(Sarcoptes spp.)、Notoedres spp.、鸟疥螨属(Knemidocoptes spp.)、鸡螨属(Cytoditesspp.)和鸡雏螨属(Laminosioptes spp.)。
例如,它们对微小牛蜱、铜绿蝇(Lucilia cuprina)和家蝇显示出突出的活性。
本发明式(I)活性化合物也适合防治侵害如下农业牲畜的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。防治这些节肢动物时,旨在避免死亡和产量降低(与肉、奶、毛、皮、蛋、蜜等等相关)。这样,采用本发明活性化合物使更经济简单的动物饲养成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过浸蘸或沐浴、喷雾、浇泼和点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当用于畜禽、家养动物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
本发明活性化合物的制备和应用可以参见下列实施例。制备实施例实施例1
CF2=CF-CH2-CONH-NH-CO-O-C2H5
伴随冷却(0至5℃)和搅拌,将溶解于10毫升二氯甲烷中的4.8克(30毫摩尔)3,4,4-三氟丁-3-烯酰基氯滴加入到由3.1克(30毫摩尔)肼基甲酸乙酯在40毫升二氯甲烷中和3.0克(30毫摩尔)三乙胺组成的溶液中。将溶液在室温下搅拌过夜,之后用乙酸乙酯萃取,有机相用稀盐酸、之后用水洗涤,并在真空下浓缩。
获得4.0克1-(乙氧基羰基)-2-(3,4,4-三氟丁-3-烯酰基)-肼,收率为理论值的59%,熔点:110℃。
生产活性化合物的适合制剂时,将1份重量的活性化合物与所述量的上述溶剂混合,并加入所述量的乳化剂,且所得的乳油用水稀释至所需浓度。
将活性化合物的制剂与土壤彻底混合,所述的土壤滋生有大量的试验线虫。在制剂中的活性化合物的浓度不是关键的,只有每单位土壤体积的活性化合物量是重要的,该量以ppm(=毫克/升)给出。将处理的土壤移至盆中,将莴苣播种于盆中,并将盆保持在25℃的室温中。
四周后,检查莴苣根的线虫(根结)感染情况,并且确定活性化合物的效力,以%计。当完全避免感染时,效力为100%,当感染水平与未处理但同样感染的土壤中的对照植株一样高时,效力为0%。
在此试验中,在示例性的20ppm活性化合物浓度下,例如制备实施例3、7和8的化合物显示出100%的效力。实施例B蝇幼虫的发育抑制作用试验试虫: 铜绿蝇(Lucilia cuprina)(OP-抗性)所有的幼虫期
[蛹和成虫(不与活性物质接触)]溶剂: 35份重量的乙二醇单甲基醚乳化剂: 35份重量的壬基苯酚聚乙二醇醚
生产适合的制剂时,将3份重量的活性化合物与7份重量的上述溶剂/乳化剂混合物混合,且所得的乳油各用水稀释至所需浓度。
对于每一浓度液,将30至50只幼虫转移到置于玻璃试管中的马肉(1cm3)上,并向此马肉用吸管移500微升试验稀释液。将玻璃试管放入底部盖有一层海沙的塑料烧杯中,并保持在恒温箱(26℃±1.5℃,70%相对温度±10%)。24和48小时后检查活性(杀幼虫作用)。在幼虫留在玻璃试管中(大约72小时)后,将试管移出,且在烧杯上盖上打了孔的塑料盖。在1.5倍于发育期(对照蝇孵化)后,该计孵化的蝇和蛹/围蛹数。
活性标准是处理幼虫48小时后的死亡率(杀幼虫效果)或抑制由蛹孵化出成虫或抑制化蛹。物质的体外活性标准是抑制蝇的发育或将发育阻止在成虫期前。100%杀幼虫活性是指所有幼虫在48小时后被杀死。100%发育抑制活性是指没孵化出成蝇。
在此试验中,在示例性的1000ppm活性化合物浓度下,例如制备实施例1、10和14的化合物显示出100%的效力。实施例C微小牛蜱(SP-抗性Parkurst品系)抗性试验试虫:自己吸足血的雌成虫溶剂:二甲基亚砜
将20mg活性物质溶于1ml二甲基亚砜中,并用相同的溶剂稀释,制成低浓度液。
试验重复5次。将1微升溶液注射入腹部,并将试虫转移到培养皿中,保持在空调室中。由抑制产卵来确定活性。100%是指没有蜱产卵。
在此试验中,在示例性的20微克/虫的活性化合物浓度下,例如制备实施例1、4、5、8、9、10、12、13、14和15的化合物显示出100%的效力。
Claims (8)
1.式(I)化合物
其中
Y 代表C=O、C=S或SO2,
R1 代表氢或卤素,且
R2 代表烷基、卤代烷基、烷氧基烷基、烷硫基烷基、环烷基、链烯基、链烯氧基、烷氧基、环烷基氧基、烷硫基或各任选取代的芳基、芳烷基、芳烷氧基或杂芳基。
2.根据权利要求1的化合物,其中
Y 代表C=O、C=S或SO2,
R1 代表氢、氟、氯或溴,且
RU 代表C1-C8-烷基、C1-C8-卤代烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷硫基-C1-C6-烷基、C3-C10-环烷基、C2-C8-链烯基、C2-C8-链烯氧基、C1-C20-烷氧基、C3-C10-环烷基氧基、C1-C20-烷硫基、各自任选由卤素-、硝基-、氰基-、氨基-、羟基-、C1-C6-烷基-、C1-C6-烷氧基-或C1-C6-烷硫基取代的苯基、苯基-C1-C4-烷基或苯基-C1-C4-烷氧基或任选由卤素-或C1-C6-烷基取代的5-或6-元杂芳基,该杂芳基具有一或二个选自氧、硫和氮的杂原子。
3.根据权利要求1的化合物,其中
Y 代表C=O、C=S或SO2,
R1 代表氢或氟,且
R2 代表C1-C6-烷基、C3-C6-环烷基、C3-C8-链烯基、C3-C8-链烯氧基、C1-C6-烷氧基、C3-C6-环烷基氧基、C1-C6-烷硫基、各自任选由氟-、氯-、溴-、羟基-、C1-C4-烷基-或C1-C4-烷氧基取代的苯基、苯基-C1-C2-烷基或苯基-C1-C2-烷氧基或各自任选由C1-C4-烷基取代的呋喃基、噻吩基或吡啶基。
6.权利要求1的式(I)化合物用于防治害虫的应用。
7.防治害虫的方法,其特征在于,使根据权利要求1的式(I)化合物作用于害虫和/或其栖息地。
8.制备杀虫剂的方法,其特征在于,将权利要求1的式(I)化合物与填充剂和/或表面活性剂混合。
9.权利要求1的式(I)化合物用于制备农药的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN 96197374 CN1241996A (zh) | 1995-08-16 | 1996-08-05 | 氟代丁烯酰基肼类化合物 |
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DE19530079.3 | 1995-08-16 | ||
CN 96197374 CN1241996A (zh) | 1995-08-16 | 1996-08-05 | 氟代丁烯酰基肼类化合物 |
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Publication Number | Publication Date |
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CN1241996A true CN1241996A (zh) | 2000-01-19 |
Family
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CN 96197374 Pending CN1241996A (zh) | 1995-08-16 | 1996-08-05 | 氟代丁烯酰基肼类化合物 |
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CN (1) | CN1241996A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106458874A (zh) * | 2014-05-23 | 2017-02-22 | 纳幕尔杜邦公司 | 甲磺酰肼化合物和用于制备4‑芳酰基吡唑衍生物的区域选择性方法 |
CN113527129A (zh) * | 2020-04-13 | 2021-10-22 | 华东理工大学 | 具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途 |
-
1996
- 1996-08-05 CN CN 96197374 patent/CN1241996A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106458874A (zh) * | 2014-05-23 | 2017-02-22 | 纳幕尔杜邦公司 | 甲磺酰肼化合物和用于制备4‑芳酰基吡唑衍生物的区域选择性方法 |
CN106458874B (zh) * | 2014-05-23 | 2018-09-14 | Fmc公司 | 甲磺酰肼化合物和用于制备4-芳酰基吡唑衍生物的区域选择性方法 |
CN113527129A (zh) * | 2020-04-13 | 2021-10-22 | 华东理工大学 | 具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途 |
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