CN100438760C - 用于种子处理的n-芳基肼衍生物 - Google Patents
用于种子处理的n-芳基肼衍生物 Download PDFInfo
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- CN100438760C CN100438760C CNB2004800361682A CN200480036168A CN100438760C CN 100438760 C CN100438760 C CN 100438760C CN B2004800361682 A CNB2004800361682 A CN B2004800361682A CN 200480036168 A CN200480036168 A CN 200480036168A CN 100438760 C CN100438760 C CN 100438760C
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Abstract
本发明涉及一种保护种子免受土壤害虫损害的方法,其包括将种子在播种之前和/或催芽之后与杀虫有效量的式(I)化合物或其对映异构体或盐接触:其中W为氯或三氟甲基;X和Y各个独立地为氯或溴;R1为烷基、链烯基、炔基或可由1-3个卤原子取代的环烷基或由烷氧基取代的烷基;R2和R3为烷基或可以连在一起形成未取代或可由1-3个卤原子取代的环烷基;R4为氢或烷基。本发明还涉及包含式(I)化合物的种子。
Description
本发明提供了一种保护种子的方法,其包括将种子在播种之前和/或催芽(pregermination)之后与杀虫有效量的式I化合物或其对映异构体或盐接触:
其中
W为氯或三氟甲基;
X和Y各个独立地为氯或溴;
R1为C1-C6烷基、C3-C6链烯基、C3-C6炔基或可由1-3个卤原子取代的C3-C6环烷基或由C1-C4烷氧基取代的C2-C4烷基;
R2和R3为C1-C6烷基或可以连在一起形成未取代或可由1-3个卤原子取代的C3-C6环烷基;
R4为氢或C1-C6烷基。
本发明也涉及包含式I化合物的种子。
本发明进一步涉及式I化合物在保护种子免受土壤害虫损害中的用途。
出现在种子保护领域的一个典型问题在于需要减少活性组分的剂量率,以减少或避免不利的环境或毒物学影响,同时仍允许有效地防治土壤害虫。
遇到的另一个问题在于需要有可利用的对宽范围的土壤害虫有效的种子保护剂。
还存在需要know-down活性与长期防治结合,即快速作用与长期持久作用结合的种子保护剂。
关于使用种子保护杀虫剂的另一个困难在于反复和单一施用单独的杀虫化合物在很多情况下导致土壤害虫出现快速的选择性,这些土壤害虫对所述活性化合物已具有天然的或者适应的耐药性。因此,需要有助于防止或克服耐药性的种子保护剂。
因此,本发明的目的是提供解决如下问题的化合物:降低剂量率和/或增强活性范围和/或结合know-down活性与长期防治结合和/或耐药性治理。
我们已经发现这些目的通过式I化合物和包含它们的组合物而部分或完全实现。
在农业领域的植物保护中,一些式I化合物的杀虫和杀螨活性已经描述于EP-A 604798以及J.A Furch等人“氨基腙:一类新的鞘翅目昆虫杀虫剂”,ACS Symposium Series 686,Am.Chem.Soc.,1998,第18章,第178页以及随后各页,以及D.G.Kuhn等人,“环烷基取代的氨基腙:一类新的昆虫防治剂”,ACS Symposium Series 686,Am.Chem.Soc.,1998,第19章,第185页以及随后各页中。
化合物在植物保护中对农业害虫的活性并没有表明它们适合保护种子,保护种子例如需要抗土壤害虫的活性,与土壤条件相容(如关于将化合物与土壤结合),施用于种子时可忽略的植物毒性以及合适的移动以获得必需的生物利用率(在土壤或植物中)。
令人惊讶的是,已发现式I化合物适合保护种子。
式I化合物可根据在EP-A 604798中描述或参考的方法或其变型方法而制备。
在上面显示的式I的定义中,取代基具有如下含义:
“卤素”是指氟、氯、溴和碘。
在此使用的术语“烷基”是指具有1-4个或1-6个碳原子的支化或无支链的饱和烃基,尤其是C1-C6烷基如甲基、乙基、丙基、1-甲基乙基、丁基,、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。
“烷氧基”是指在烷基的任何键上通过氧键而键接的具有1-4个碳原子的直链或支链烷基(甲基、乙基、丙基、1-甲基乙基、丁基,1-甲基丙基、2-甲基丙基、1,1-二甲基乙基)。实例包括甲氧基、乙氧基、丙氧基和异丙氧基。
“环烷基”是指3-6个碳原子的饱和单环基,即环丙基、环丁基、环戊基和环己基。
对于意欲使用的式I化合物,特别优选如下含义的取代基,在每种情况下为它们本身或组合:
优选其中W为三氟甲基的式I化合物。
进一步优选其中W和Y都为氯的式I化合物。
此外,优选其中R1为C1-C6烷基,尤其是乙基的式I化合物。
进一步优选其中R2和R3都为甲基的式I化合物。
此外,优选其中R2和R3形成未取代或由1-3个卤原子,尤其是氯和溴取代的环丙基环的式I化合物。
此外,特别优选其中R2和R3形成由2个卤原子取代的环丙基环的式I化合物。
此外,特别优选其中R2和R3形成由2个氯原子取代的环丙基环的式I化合物。
特别优选其中R2和R3形成2,2-二氯代环丙基环的式I化合物。
进一步优选其中R4为C1-C6烷基,尤其是甲基的式I化合物。
特别优选其中R2、R3和R4都为甲基的式I化合物。
此外,特别优选其中R2、R3和R4形成1-甲基-2,2-二氯代环丙基部分的式I化合物。
进一步优选其中各个变量如下的式I化合物或其对映异构体或盐:
W为三氟甲基;
X和Y各个独立地为氯或溴;
R1为C1-C6烷基;
R2和R3为C1-C6烷基或可以连在一起形成由1-2个卤原子取代的C3-C6环烷基;
R4为C1-C6烷基。
特别优选N-乙基-2,2-二甲基丙酰胺基-2-(2,6-二氯代-α,α,α-三氟-对甲苯基)腙和N-乙基-2,2-氯代-1-甲基环丙烷甲酰胺-2-(2,6-二氯代-α,α,α-三氟-对甲苯基)腙。
此外,对于本发明用途特别优选式I-1化合物(N-乙基-2,2-二甲基丙酰胺基-2-(2,6-二氯代-α,α,α-三氟-对甲苯基)腙):
此外,对于本发明用途特别优选式I-2化合物(N-乙基-2,2-氯代-1-甲基环丙烷甲酰胺基-2-(2,6-二氯代-α,α,α-三氟-对甲苯基)腙):
对于它们的用途,特别优选汇集于下表的化合物I-A。此外,所述取代基的特别优选的实施方案,在表中提及的作为取代基的基团是独立的,与其中提及它们的组合无关。
对于它们的用途,还特别优选下表化合物与盐酸、马来酸、二马来酸、富马酸、二富马酸、甲烷次磺酸、甲磺酸和琥珀酸的加合物。
表A
式I化合物适合保护种子免受土壤害虫损害,尤其是免受选自下列的害虫损害:
千足虫(倍足纲(Diplopoda))、半翅目(同翅目(Homoptera)和异翅目(Heteroptera))、直翅目(Orthoptera),
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ipsilon)、黄地老虎(Agrotis segetum),Chilo ssp.、Euxoa ssp.、Momphidae、玉米螟(Ostrinia nubilalis)和马铃薯麦蛾(Phthorimaea operculella),
甲虫(鞘翅目(Coleoptera)),例如直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Aphthona euphoridae、Athoushaemorrhoidalis、甜菜隐食甲(Atomaria linearis)、Cetonia aurata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis),Ctenicera ssp.、Diabrotica longicornis、南美叶甲(Diabrotica speciosa)、Diabrotica semi-punctata、玉米根叶甲(Diabrotica virgifera)、Limonius californicus、Melanotus communis、草莓根象甲(Otiorrhynchus ovatus)、梨树叶象(Phyllobius pyri)、食叶鳃金龟属(Phyllophaga sp.)、Phyllophaga cuyabana、Phyllophaga triticophaga、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotretanemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popilliajaponica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilus granaria),
蝇类(双翅目(Diptera)),例如蛆症金蝇(Chrysomya bezziana)、Chrysomya hominivorax、Chrysomya macellaria、高粱瘿蚊(Contariniasorghicola)、Cordylobia anthropophaga、瓜实蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia antique、Delia coarctata、Delia platura、Delia radicum、小毛厕蝇(Fanniacanicularis)、马蝇(Gasterophilus intestinalis)、Geomyza Tripunctata、刺舌蝇(Glossina morsitans)、Haematobia irritans、Haplodiplosis equestris、纹皮蝇(Hypoderma lineata)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、小麦瘿蚊(Mayetioladestructor)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、Opomyzaflorum、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、Phorbia antiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、Psilarosae、樱桃绕实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、Tabanus bovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa),
蓟马(缨翅目(Thysanoptera))如烟蓟马(Thrips tabaci),
蚁类(膜翅目(Hymenoptera)如Atta capiguara、切叶蚁(Attacephalotes)、Atta laevigata、Atta robusta、Atta sexdens、Atta texana、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsis geminata)和红火蚁(Solenopsis invicta)、红蚂蚁亚种(Pogonomyrmex ssp.)以及Pheidolemegacephala,
白蚁类(等翅目(Isoptera)),例如乳白蚁亚种(Coptotermes ssp),跳虫(弹尾目(Collembola)),例如Onychiurus ssp。
本发明混合物尤其适合对抗双翅目、鞘翅目、鳞翅目和等翅目类害虫。
此外,式I化合物和含有它们的组合物尤其优选用于对抗双翅目类害虫,尤其是蝇(Delia)类。
式I化合物和含有它们的组合物用于对抗鞘翅目,尤其是叶甲(Diabrotica)类和叩头虫科(Elateridae)(线虫)是本发明的另一优选实施方案。
此外,式I化合物和含有它们的组合物尤其优选用于对抗等翅目类害虫。
式I化合物可以用来保护种子以及种子的根和芽免受土壤害虫损害。优选保护种子。
尤其优选的是保护谷类(如小麦、大麦、黑麦)、油菜(canola)、甜菜、玉米、高粱、向日葵、棉花、稻、豌豆、菜籽(colza)、马铃薯以及商品菜园作物如稻、小麦、大麦或黑麦的种子。
式I化合物通过直接和间接接触和摄食以及通过交哺和转移都是有效的。
常规的种子处理配制剂例如包括可流动浓缩物FS、溶液LS、干燥处理用粉末DS、水分散性粉末WS或用于浆液处理的颗粒、水溶性粉末SS和乳液ES。对种子施用在播种前进行,或直接施用在种子上或在将种子催芽后进行。
对于本发明用途,可将化合物I转化为常规配制剂如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。施用形式取决于特定的目的;根据本发明,在每种情况下,应确保化合物在种子上精细且均匀地分布。
配制剂以已知方式制备,例如通过将活性组分与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。合适的溶剂/助剂主要为:-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂为木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘与甲醛的缩合物和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚、辛基酚、壬基酚的缩合物,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素以及氧化乙烯/氧化丙烯嵌段共聚物。
适于制备可直接喷雾的溶液、乳液、糊或油分散体的物质为中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或一起研磨来制备。
颗粒如涂敷颗粒、浸渍颗粒和均质颗粒可以通过使活性组分与固体载体粘附而制备。固体载体实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
在处理之后,可加入粘着剂/粘合剂以改进活性材料在种子上的附着。合适的粘合剂为EO/PO嵌段共聚物表面活性剂以及聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺(Lupasol,Polymin)、聚醚、聚氨酯以及衍生于这些聚合物的共聚物。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性组分。活性化组分以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.直接施用的产品或用水稀释后施用的产品
A)可溶性浓缩物(LS)
将10重量份活性化合物溶于水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于环己酮中并加入分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。
C)可乳化的浓缩物(EC)
将15重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。用水稀释得到乳液。D)乳液(ES)
将40重量份活性化合物溶于二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下浓度为5%)。借助乳化机(Ultraturrax)将该混合物引入水中并制成均相乳液。用水稀释得到乳液。
E)悬浮液(FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入分散剂、湿润剂和水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。
F)水分散性颗粒和水溶性颗粒(WG,SG)
将50重量份活性化合物细碎研磨并加入分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。
G)水分散性粉末和水溶性粉末(SS,WS)
将75重量份活性化合物在转子-定子磨中研磨并加入分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。
2.不经稀释而施用的产品
H)可撒粉粉末(DS)
将5重量份活性化合物细碎研磨并与95%的细碎高岭土充分混合。这得到可撒粉产品。
I)颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合95.5%载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的颗粒。
活性组分可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、凝胶、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒,微胶囊(CS)、丸粒或片形式),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性组分的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。或者,可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂和若合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
即用产品中的活性组分浓度可在较宽范围内变化。它们通常为0.01-80%,优选0.1-50%。
各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂都可加入活性组分中,若合适的话,恰在紧邻使用前加入。这些试剂通常与本发明试剂以1∶100-100∶1的重量比混合。
优选FS配制剂。
优选的用于种子处理的式I化合物的FS配制剂包含0.5-80%活性组分,0.05-5%湿润剂,0.5-15%分散剂,0.1-5%增稠剂,5-20%防冻剂,0.1-2%消泡剂,1-20%颜料和/或染料,0-15%粘着剂/粘合剂,0-75%填料/赋形剂和0.01-1%防腐剂。
在种子处理中,混合物的施用率通常为0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1-200g/100kg种子。
在害虫防治中,式I化合物或包含它的组合物的施用通过在播种后对种子或土壤(以及其中的种子)喷雾或撒粉而进行。
本发明的另一目的是一种用含活性组分或包含它的组合物的颗粒配制剂,用任选一种或多种固体或液体的农业可接受载体和/或任选用一种或多种农业可接受表面活性剂,在条播机中处理种子的方法。这种方法有利地用于谷类、玉米、棉花和向日葵的苗床中。对于谷类和玉米,式I化合物的施用率为50-500g/ha。
本发明也涉及植物的繁殖产品以及尤其是包含,即“涂覆和/或含有”,式I化合物或包含它的组合物的处理过的种子。术语“涂覆和/或含有”通常指在施用时,绝大部分活性组分在繁殖产品的表面,尽管取决于施用方法,或多或少的组分可能渗入繁殖产品。当将所述繁殖产品(再)种植时,它可能吸附活性物质。
种子包含本发明混合物的量为0.1g-10kg/100kg种子。
可与本发明化合物一起使用的下列农药意欲阐述可能的组合,而不施以任何限制。
有机磷酸酯类:高灭磷(Acephate)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异噁唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、特丁磷(Terbufos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
氨基甲酸酯类:棉铃威(Alanycarb)、丙硫克百威(Benfuracarb)、甲萘威(Carbaryl)、丁硫克百威(Carbosulfan)、双氧威(Fenoxycarb)、呋线威(Furathiocarb)、噁二唑虫(Indoxacarb)、灭虫威(Methiocarb)、灭多虫(Methomyl)、甲氨叉威(Oxamyl)、抗蚜威(Pirimicarb)、残杀威(Propoxur)、硫双威(Thiodicarb)、唑蚜威(Triazamate);
合成除虫菊酯类:氟氯菊酯(Bifenthrin)、氟氯氰菊酯(Cyfluthrin)、氯氰菊酯(Cypermethrin)、α-氯氰菊酯(alpha-Cypermethrin)、溴氰菊酯(Deltamethrin)、高氰戊菊酯(Esfenvalerate)、醚菊酯(Ethofenprox)、甲氰菊酯(Fenpropathrin)、杀灭菊酯(Fenvalerate)、(RS)氯氟氰菊酯(Cyhalothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(Permethrin)、灭虫硅醚(Silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(Tefluthrin)、四溴菊酯(Tralomethrin)、己体氯氰菊酯(Zeta-Cypermethrin);节肢动物生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(Chlorfluazuron)、氟脲杀(Diflubenzuron)、氟螨脲(Flucycloxuron)、氟虫脲(Flufenoxuron)、氟铃脲(Hexaflumuron)、氟丙氧脲(Lufenuron)、双苯氟脲(Novaluron)、伏虫隆(Teflubenzuron)、杀虫隆(Triflumuron);噻嗪酮(Buprofezin)、噁茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯噁唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(Halofenozide)、甲氧苯酰肼(Methoxyfenozide)、双苯酰肼(Tebufenozide);c)保幼激素类似物:蚊蝇醚(Pyriproxyfen)、蒙五一五(Methoprene)、双氧威(Fenoxycarb);d)类脂生物合成抑制剂:螺螨酯(Spirodiclofen);
新烟碱类(Neonicotinoids):吡虫清(Acetamiprid)、噻虫胺(Clothianidin)、氟啶虫酰胺(Flonicamid)、吡虫啉(Imidacloprid)、硝胺烯啶(Nitenpyram)、噻虫啉(Thi acloprid)、噻虫嗪(Thiamethoxam);
各种其它杀虫剂:齐墩螨素(Abamectin)、灭螨醌(Acequinocyl)、虫螨脒(Amitraz)、艾扎丁(Azadirachtin)、联苯肼酯(Bifenazate)、苏金杆菌(Bacillusthuringiensis)、柯敌克菌(Bacillus subtilis)、杀螟丹(C artap)、氟唑虫清(Chlorfenapyr)、杀虫脒(Chlordimeform)、灭蝇胺(Cyromazine)、杀螨硫隆(Diafenthiuron)、呋虫胺(Dinetofuran)、噁茂醚(Diofenolan)、埃玛菌素(Emamectin)、硫丹(Endosulfan)、Ethiprole、喹螨醚(Fenazaquin)、锐劲特(Fipronil)、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanatehydrochloride)、灭蚁腙(Hydramethylnon)、噁二唑虫(Indoxacarb)、4-{(2Z)-2-({[4-(三氟甲氧基)苯胺基]羰基}亚肼基)-2-[3-(三氟甲基)-苯基]乙基}苄腈、哒螨酮(Pyridaben)、拒嗪酮(Pymetrozine)、艾克敌105(Spinosad)、硫(Sulfur)、吡螨胺(Tebufenpyrad)、和硫环杀(Thiocyclam)。
“杀虫有效量”通常指对生长获得可观察到的效果所需要活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活性的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量的也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
通过如下试验说明化合物的杀虫作用:
玉米根虫、线虫和玉米种子蛆种子处理分析
保护种子免受南部玉米根虫,黄瓜十一星叶甲(Diabroticaundecimpunctata howardi)(幼虫),线虫,Agriotis lineatus(幼虫)以及玉米种子蛆,灰地种蝇(Delia platura)(卵)损害。
在由15%丙酮和0.05%Tween 20TM(聚氧乙烯脱水山梨醇单月桂酸酯)组成的在水中的溶剂-表面活性剂载体中配制活性化合物。
在玻璃瓶中,用许多50并用450μl化合物制剂摇动处理玉米种子(玉米“Truckers Favorite”),并将其干燥。在盖上具有气孔的每个120ml的容器中的沙质壤土上种植一个种子。每个容器中加入十个昆虫卵或幼虫。种植7天后评价卵或幼虫的死亡率以及对根和芽的摄食损害。
与空白溶剂-表面活性剂对照对比来计算昆虫死亡率和摄食损害百分数。
在251g活性组分/100kg种子时,化合物I-1和I-2保护了30%以上的种子和秧苗免受线虫摄食损害。
Claims (7)
2.根据权利要求1的方法,其中以0.1g-10kg/100kg种子的量施用式I化合物。
3.根据权利要求1的方法,其中以1-2g/100kg种子的量施用式I化合物。
6.根据权利要求1-5中任一项的方法,其中保护种子免受双翅目、鳞翅目、鞘翅目和等翅目类土壤害虫损害。
7.如权利要求1、4或5中所定义的式I化合物在保护种子免受土壤害虫损害中的用途。
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CNB2004800361682A Expired - Fee Related CN100438760C (zh) | 2003-12-04 | 2004-12-02 | 用于种子处理的n-芳基肼衍生物 |
CNA2004800361663A Pending CN1889833A (zh) | 2003-12-04 | 2004-12-02 | N-芳基肼衍生物在动物中和动物上防治害虫的用途 |
CNA2004800361659A Pending CN1889832A (zh) | 2003-12-04 | 2004-12-02 | N-芳基肼衍生物在防治非作物害虫中的用途 |
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CNA2004800361663A Pending CN1889833A (zh) | 2003-12-04 | 2004-12-02 | N-芳基肼衍生物在动物中和动物上防治害虫的用途 |
CNA2004800361659A Pending CN1889832A (zh) | 2003-12-04 | 2004-12-02 | N-芳基肼衍生物在防治非作物害虫中的用途 |
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US (2) | US20070129442A1 (zh) |
EP (3) | EP1691607B1 (zh) |
JP (3) | JP2007513117A (zh) |
KR (3) | KR20060115889A (zh) |
CN (3) | CN100438760C (zh) |
AP (1) | AP1959A (zh) |
AR (2) | AR046746A1 (zh) |
AT (3) | ATE372674T1 (zh) |
AU (3) | AU2004294299A1 (zh) |
BR (3) | BRPI0417181A (zh) |
CA (3) | CA2547420A1 (zh) |
CO (2) | CO5680375A2 (zh) |
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DE (3) | DE602004019995D1 (zh) |
DK (2) | DK1691607T3 (zh) |
EA (3) | EA200601077A1 (zh) |
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IL (3) | IL175544A0 (zh) |
MA (2) | MA28280A1 (zh) |
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MY (1) | MY137761A (zh) |
NO (1) | NO20062632L (zh) |
NZ (1) | NZ547362A (zh) |
OA (1) | OA13292A (zh) |
PE (1) | PE20050702A1 (zh) |
PL (2) | PL1691607T3 (zh) |
PT (1) | PT1691607E (zh) |
SI (2) | SI1694122T1 (zh) |
TW (3) | TW200529836A (zh) |
UA (2) | UA79571C2 (zh) |
UY (2) | UY28654A1 (zh) |
WO (3) | WO2005053402A2 (zh) |
ZA (3) | ZA200605458B (zh) |
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EA200702537A1 (ru) * | 2005-06-03 | 2008-06-30 | Басф Акциенгезельшафт | Композиция для пропитки нитей, тканей и сетчатых материалов, обеспечивающая защиту от вредителей |
EP1895839A1 (en) * | 2005-06-03 | 2008-03-12 | Basf Se | Method of combating bugs |
WO2007051756A1 (en) * | 2005-11-04 | 2007-05-10 | Basf Se | Crystalline modification of n-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro- alpha,alpha,alpha -trifluoro-p-tolyl)hydrazone |
RU2008126713A (ru) * | 2005-12-01 | 2010-01-10 | Сумитомо Кемикал Компани, Лимитед (Jp) | Иминопропеновое соединения и его применение |
JP5239148B2 (ja) * | 2005-12-01 | 2013-07-17 | 住友化学株式会社 | 3−イミノプロペン化合物、それを含有する有害生物防除剤、およびその有害生物防除用途 |
AP2008004548A0 (en) * | 2006-01-04 | 2008-08-31 | Basf Se | Method of combating root weevils |
US20080300313A1 (en) * | 2006-01-05 | 2008-12-04 | Thomas Byrne | Solvent Mixture for Preparing Water-Dilutable Liquid Concentrate Formulation of Organic Pesticide Compounds |
DE102006011403A1 (de) * | 2006-03-11 | 2007-09-13 | Bayer Cropscience Ag | Köder auf Zuckerbasis |
JP2009545552A (ja) * | 2006-08-03 | 2009-12-24 | ビーエーエスエフ ソシエタス・ヨーロピア | アミドラゾンの調製方法 |
DE102006061537A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Healthcare Ag | Mittel zur Bekämpfung von Parasiten an Tieren |
WO2008092851A2 (en) * | 2007-01-30 | 2008-08-07 | Basf Se | Pesticidal compositions comprising 3 -acetyl-i- phenylpyrazole compounds |
US20100099774A1 (en) * | 2007-02-01 | 2010-04-22 | Basf Se | Method for Controlling Harmful Fungi |
WO2008092818A2 (en) * | 2007-02-01 | 2008-08-07 | Basf Se | Pesticidal mixtures |
MX2010004578A (es) * | 2007-10-25 | 2010-07-28 | Valent Biosciences Corp | Mejoras de crecimiento de plantas. |
WO2009059603A1 (en) | 2007-11-05 | 2009-05-14 | Vestergaard Frandsen Sa | Room with two counter-resistant insecticidal objects |
CN101747320B (zh) * | 2008-12-19 | 2013-10-16 | 华东理工大学 | 二醛构建的具有杀虫活性的含氮或氧杂环化合物及其制备方法 |
CA2803687C (en) | 2010-07-20 | 2019-04-30 | Vestaron Corporation | Insecticidal triazines and pyrimidines |
AU2013245011B2 (en) * | 2012-04-04 | 2017-11-23 | Intervet International B.V. | Solid oral pharmaceutical compositions for isoxazoline compounds |
US9108932B2 (en) | 2013-03-13 | 2015-08-18 | Dow Agrosciences Llc | Preparation of haloalkoxyarylhydrazines and intermediates therefrom |
US9212150B2 (en) | 2013-03-13 | 2015-12-15 | Dow Agrosciences Llc | Process for the preparation of certain triaryl pesticide intermediates |
JP6487426B2 (ja) | 2013-10-17 | 2019-03-20 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除化合物の調製法 |
US10233155B2 (en) | 2016-12-29 | 2019-03-19 | Dow Agrosciences Llc | Processes for the preparation of pesticide compounds |
CN115251086A (zh) * | 2022-08-03 | 2022-11-01 | 广州毅田生物技术有限公司 | 一种含绿僵菌的红火蚁防治药剂及其防治方法 |
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CN1089938A (zh) * | 1992-12-29 | 1994-07-27 | 美国氰胺公司 | 用作杀虫剂和杀螨剂的n-芳基肼衍生物 |
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JPS5576804A (en) * | 1978-12-06 | 1980-06-10 | Sankyo Co Ltd | Agricultural and horticultural microbicide |
US5420165A (en) * | 1992-12-29 | 1995-05-30 | American Cyanamid Company | Amidrazones and their use as insecticidal and acaricidal agents |
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Patent Citations (1)
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