CN1859850A - 防治稻病原体的杀真菌混合物 - Google Patents
防治稻病原体的杀真菌混合物 Download PDFInfo
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- CN1859850A CN1859850A CN 200480028433 CN200480028433A CN1859850A CN 1859850 A CN1859850 A CN 1859850A CN 200480028433 CN200480028433 CN 200480028433 CN 200480028433 A CN200480028433 A CN 200480028433A CN 1859850 A CN1859850 A CN 1859850A
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Abstract
本发明涉及以协同有效量包含下列化合物作为活性组分的防治稻病原体的杀真菌混合物：1)式(I)的三唑并嘧啶衍生物和2)式(II)的肟菌酯，使用化合物(I)和化合物(II)的混合物防治稻病原体的方法，化合物(I)和化合物(II)在制备该混合物中的用途，以及包含该混合物的组合物。
Description
本发明涉及防治稻病原体的杀真菌混合物，该混合物以协同有效量包含如下化合物作为活性组分：
1)式I的三唑并嘧啶衍生物：
和
2)式II的肟菌酯(trifloxystrobin)：
此外，本发明还涉及使用化合物I和化合物II的混合物防治稻病原体的方法，化合物I和化合物II在制备该类混合物中的用途，以及包含该混合物的组合物。
化合物I，即5-氯-7-(4-甲基哌啶-1-基)-6-(2，4，6-三氟苯基)-[1，2，4]三唑并[1，5-a]嘧啶，其制备及其对有害真菌的作用由文献(WO 98/46607)已知。
化合物II，即(E)-甲氧基亚胺基-{(E)-α-[1-(α，α，α-三氟间甲苯基)亚乙基氨基氧基]-邻甲苯基}乙酸甲酯，其制备及其抵抗有害真菌的作用还由文献(EP-A 460575；通用名：肟菌酯)已知。肟菌酯已经在市场上销售，主要作为用于禾谷类的抵抗由子囊菌纲(Ascomycetes)或担子菌纲(Basidiomycetes)真菌引起的霉病和锈病的杀真菌剂。
三唑并嘧啶衍生物与肟菌酯(CGA-279202)的混合物以一般方式由EP-A 988 790已知。化合物I包括在该出版物的一般性公开中，但没有得到清楚的说明。因此，化合物I和肟菌酯的组合是新的。
由EP-A 988 790已知的协同增效混合物描述为对禾谷类、水果和蔬菜的各种病害，例如小麦和大麦上的霉病或苹果上的灰霉病具有杀真菌活性。
由于稻类植物的特殊栽培条件，稻用杀真菌剂需要满足的要求显著不同于禾谷类或水果生长中使用的杀真菌剂所需要满足的要求。在施用方法上有差别：除了在很多情况下使用的叶面施用方法以外，在现代稻类种植中，将杀真菌剂在播种过程中或者在播种以后的短时间内直接施加于土壤上。杀真菌剂由根部吸收到植物中，并且在植物的汁液中输送到待保护的植物部分。相反，在禾谷类或水果生长中，杀真菌剂通常施用于叶子或果实上；因此，在这些作物中活性化合物的内吸作用明显不太重要。
此外，稻病原体通常不同于禾谷类或水果中的病原体。稻瘟病菌(Pyricularia oryzae)、宫部旋孢腔菌(Cochliobolus miyabeanus)和笹木伏革菌(Corticium sasakii，同义词：立枯丝核菌(Rhizoctonia solani))是稻类植物中最普遍的病害病原体。立枯丝核菌是来自Agaricomycetidae亚纲的唯一具有农业重要性的病原体。与大多数其它真菌不同，该真菌不是由孢子而是由菌丝体侵染而侵害植物。
为此，有关禾谷类或水果栽培中的杀真菌活性的发现并不能用于稻类作物。
农业实践经验已经表明在有害真菌的防治中重复和单独施用单一活性化合物在许多情况下导致真菌菌株的快速选择，该菌株对所述活性化合物已经产生天然或适应性的抗药性。因而不能再用所述活性化合物有效防治这些真菌。
为了降低抗药性真菌菌株的选择危险，现在通常采用不同活性化合物的混合物来防治有害真菌。通过组合具有不同作用机理的活性化合物，可以确保较长时间的成功防治。
为了对稻病原体进行有效抗药性管理和以尽量小的施用率进行有效防治，本发明的目的是提供在活性化合物的施用总量减少下具有改进的抗有害真菌效果的混合物。
我们发现该目的通过开头定义的混合物实现。此外，我们发现与施用单一化合物可能产生的效果相比，同时，即联合或分别施用化合物I和化合物II或者依次施用化合物I和化合物II能够更好地防治稻病原体。
当制备该混合物时，优选采用纯活性化合物I和II，根据需要可以向其中加入抵抗有害真菌或其它害虫如昆虫、蜘蛛或线虫的其它活性化合物，或者除草或生长调节活性化合物或肥料。
具有上述含义的其它合适活性化合物特别是选自下列的杀真菌剂：
·酰基丙氨酸类，例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(oxadixyl)，
·胺衍生物类，例如aldimorph、吗菌灵(dodemorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)或克啉菌(tridemorph)，
·抗菌素类，例如放线菌酮(cycloheximid)、灰黄霉素(griseofulvin)、春雷霉素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin)，
·唑类，例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(dinitroconazole)、烯菌灵(enilconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑醇(ipconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、prothioconazole、硅氟唑(simeconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)或戊叉唑菌(triticonazole)，
·二羧酰亚胺类，例如甲菌利(mycozolin)或杀菌利(procymidone)，
·二硫代氨基甲酸盐类，例如福美铁(ferbam)、代森钠(nabam)、威百亩(metam)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美锌(ziram)或代森锌(zineb)，
·杂环化合物类，例如敌菌灵(anilazine)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、唑酮菌(famoxadone)、咪唑菌酮(fenamidon)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolan)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、噻菌灵(probenazole)、咯喹酮(pyroquilon)、硅噻菌胺(silthiofam)、涕必灵(thiabendazol)、溴氟唑菌(thifluzamid)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)或嗪氨灵(triforine)，
·硝基苯基衍生物类，例如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)或异丙消(nitrophthalisopropyl)，
·苯基吡咯类，例如拌种咯(fenpiclonil)或氟菌(fludioxonil)，
·硫，
·其它杀真菌剂类，例如噻二唑素(acibenzolar-S-methyl)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、cyflufenamid、清菌脲(cymoxanil)、哒菌清(diclomezin)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenone)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(toloclofos-methyl)、五氯硝基苯(quintozene)或苯酰菌胺(zoxamide)，
·亚胺菌类，例如氟嘧菌酯(fluoxastrobin)、苯氧菌胺(metominostrobin)、肟醚菌胺(orysastrobin)或唑菌胺酯(pyraclostrobin)，
·次磺酸衍生物类，例如敌菌丹(captafol)，
·肉桂酰胺类及类似化合物，例如氟联苯菌(flumetover)。
在本发明混合物的一个实施方案中，可以将其它杀真菌剂III或两种杀真菌剂III和IV加入化合物I和II中。优选化合物I和II与组分III的混合物。特别优选化合物I和II的混合物。
化合物I和化合物II的混合物或者同时，即联合或分别使用的化合物I和化合物II对来自子囊菌纲、半知菌纲(Deuteromycetes)或担子菌纲的稻病原体呈现显著的作用。它们可以用于种子处理和作为叶面作用或土壤作用的杀真菌剂。优选通过喷雾叶子而施用化合物I和II。还可以通过施用颗粒或通过对土壤撒粉而施用化合物。
它们对于防治稻类植物及其种子上的有害真菌，如平脐孢(Bipolaris)属和内脐孢(Drechslera)属以及稻瘟病菌特别重要。它们特别适于防治由稻瘟病菌引起的稻瘟病和宫部旋孢腔菌引起的稻类褐斑病。
此外，本发明化合物I和II的组合还适于防治其他病原体，如禾谷类中的壳针孢(Septoria)属和柄锈菌(Puccinia)属以及蔬菜、水果和葡萄藤中的链格孢(Alternaria)属和葡萄孢(Botrytis)属。
可以同时，即联合或分别施用或者依次施用化合物I和化合物II，在分别施用的情况下，施用顺序通常不会对防治措施的结果产生任何影响。
通常，化合物I和化合物II以100∶1至1∶100，优选20∶1至1∶50，更优选10∶1至1∶10，特别是10∶1至1∶5的重量比施用。
如果需要，组分III和合适的话IV以20∶1至1∶20的比例加入化合物I中。
取决于化合物的类型和所需效果，本发明混合物的施用率是5g/ha至2000g/ha，优选50-1500g/ha，特别是50-750g/ha。
相应地，化合物I的施用率通常是1-1000g/ha，优选10-750g/ha，特别是20-500g/ha。
相应地，化合物II的施用率通常是1-1000g/ha，优选10-750g/ha，特别是20-500g/ha。
在种子的处理中，混合物的施用率通常是1-1000g/100kg种子，优选1-750g/100kg种子，特别是5-500g/100kg种子。
在稻类植物的致病有害真菌的防治中，通过在播种植物之前或之后或者在植物出苗之前或之后对种子、秧苗、植物或土壤进行喷雾或撒粉而分别或联合施用化合物I和II或者化合物I和II的混合物。
本发明混合物或者化合物I和化合物II可以转化为常用配制剂，例如溶液、乳液、悬浮液、粉剂、粉末、糊或颗粒。施用形式取决于特定的目的；在每种情况下，该形式应当确保本发明化合物的精细和均匀分布。
以已知方式制备配制剂，例如通过使活性化合物与溶剂和/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/助剂基本上是：
-水，芳族溶剂(例如Solvesso产品，二甲苯)，石蜡(例如矿物油馏分)，醇(例如甲醇、丁醇、戊醇、苯甲醇)，酮(例如环己酮、γ-丁内酯)，吡咯烷酮(NMP、NOP)，乙酸酯(乙二醇二乙酸酯)，二醇，脂肪酸二甲基酰胺，脂肪酸和脂肪酸酯。原则上还可以使用溶剂混合物，
-载体如磨碎的天然矿物(例如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(例如高度分散的二氧化硅、硅酸盐)；乳化剂如非离子和阴离子乳化剂(例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。
合适的表面活性剂是木素磺酸、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，此外还有磺化萘和萘衍生物与甲醛的缩合物，萘或萘磺酸与苯酚和甲醛的缩合物，聚氧乙烯辛基苯基醚，乙氧基化异辛基酚，辛基酚，壬基酚，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。
适于制备可直接喷雾的溶液、乳液、糊或油分散体的物质是具有中至高沸点的矿物油馏分如煤油或柴油，此外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-甲基吡咯烷酮或水。
可以通过混合或同时研磨活性物质和固体载体而制备粉末、撒播材料和可撒粉产品。
可以通过将活性化合物粘附到固体载体上而制备颗粒如涂敷颗粒、浸渍颗粒和均质颗粒。固体载体的实例是矿土如硅胶、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，以及其它固体载体。
配制剂通常包含0.01-95重量％，优选0.1-90重量％的活性化合物。活性化合物以90-100％，优选95-100％(根据NMR波谱)的纯度使用。
以下是配制剂的实例：
1.用水稀释的产品
A)水溶性浓缩物(SL)
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)乳油(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(EW，EO)
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(Ultraturax)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(SC，OD)
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(WP，SP)
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(DP)
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。
J)ULV溶液(UL)
将10重量份活性化合物溶于有机溶剂如二甲苯中。这得到不经稀释而施用的产品。
活性化合物可以直接、以其配制剂形式或由其制备的使用形式，例如以可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播材料或颗粒形式，借助喷雾、雾化、撒粉、撒播或浇灌而使用。使用形式完全取决于预期目的；意欲在每种情况下确保本发明活性化合物尽可能最精细地分布。
含水使用形式可以通过加入水而由乳液浓缩物、糊或可润湿粉末(可喷雾粉末、油分散体)制备。为了制备乳液、糊或油分散体，可以借助润湿剂、增粘剂、分散剂或乳化剂将该物质直接或在溶于油或溶剂中后在水中均化。或者，还可以制备由活性物质、润湿剂、增粘剂、分散剂或乳化剂以及合适的话还有溶剂或油组成的浓缩物，并且该浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可以在较宽范围内变化。通常该浓度为0.0001-10％，优选0.01-1％。
活性化合物还可以成功用于超低容量法(ULV)，通过该方法可以施用包含超过95重量％的活性化合物的配制剂，或者甚至施用不含添加剂的活性化合物。
可以将各种类型的油、润湿剂、助剂、除草剂、杀真菌剂、其它农药或杀菌剂加入活性化合物中，如果合适的话，恰在紧邻使用前加入(桶混合)。这些试剂通常与本发明试剂以1∶10至10∶1的重量比混合。
通过用杀真菌有效量的混合物，或者在分别施用的情况下用化合物I和II处理有害真菌，或者需要防止有害真菌侵袭的植物、种子、土壤、区域、材料或空间而施用化合物I和II或其混合物或相应的配制剂。可以在受到有害真菌侵染之前或之后施用。
化合物和混合物的杀真菌作用可以通过下列实验进行说明：
将活性化合物分别或联合制备成含有0.25重量％活性化合物的丙酮或DMSO储液。将1重量％的乳化剂UniperolEL(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)加入该溶液中，并将溶液用水稀释到所需浓度。
应用实施例1-对稻瘟病菌引起的稻瘟病的保护活性
用具有下述活性化合物浓度的含水悬浮液对栽培品种为“Tai-Nong67”的盆栽稻秧苗的叶子喷雾至滴流点。第二天，用稻瘟病菌的孢子含水悬浮液接种植物。然后将测试植物置于22-24℃和95-99％相对大气湿度的气候室中6天。然后肉眼测定叶子上的侵染发展程度。
通过确定侵染植物的百分数而进行评价。将这些百分数转化成效力。
使用Abbot公式按如下计算效力(E)：
E＝(1-α/β)·100
α对应于处理植物的真菌侵染百分数，和
β对应于未处理(对照)植物的真菌侵染百分数。
效力为0表示处理植物的侵染水平对应于未处理的对照植物；效力为100表示处理植物未受侵染。
使用Colby公式确定活性化合物的混合物的预期效力(R.S.Colby，Weeds(杂草)，15，第20-22页，1967)，并与观察的效力进行比较。
Colby公式：E＝x+y-x·y/100
E使用浓度为a和b的活性化合物A和B的混合物时的预期效力，以相对于未处理对照的％表示，
x使用浓度为a的活性化合物A时的效力，以相对于未处理对照的％表示，
y使用浓度为b的活性化合物B时的效力，以相对于未处理对照的％表示。
使用由EP-A 988 790中所述的肟菌酯混合物已知的化合物A和B作为对比化合物：
表A-单一活性化合物
| 实施例 | 活性化合物 | 活性化合物在喷雾液体中的浓度[ppm] | 效力，相对于未处理对照的％ |
| 1 | 对照(未处理) | - | (60％侵染) |
| 2 | I | 16 | 67 |
| 3 | II(肟菌酯) | 164 | 22 |
| 4 | 对比化合物A | 16 | 59 |
| 5 | 对比化合物B | 16 | 67 |
表B-本发明混合物
| 实施例 | 活性化合物的混合物浓度混合比 | 观察的效力 | 计算的效力*) |
| 6 | I+II16+4ppm4∶1 | 92 | 68 |
| 7 | I+II16+16ppm1∶1 | 100 | 68 |
*)使用Colby公式计算的效力
表C-对比测试
| 实施例 | 活性化合物的混合物浓度混合比 | 观察的效力 | 计算的效力*) |
| 8 | A+II16+4ppm4∶1 | 67 | 60 |
| 9 | A+II16+16ppm1∶1 | 67 | 60 |
| 10 | B+II16+4ppm4∶1 | 67 | 68 |
| 11 | B+II16+16ppm1∶1 | 76 | 68 |
*)使用Colby公式计算的效力
测试结果表明，由于强协同增效作用，对于抵抗稻瘟病，本发明的混合物比由EP-A 988 790已知的对比化合物的肟菌酯混合物显著更有效。
应用实施例2-对宫部旋孢腔菌引起的稻褐斑病的活性，保护性施用
用具有下述活性化合物浓度的含水悬浮液对栽培品种为“Tai-Nong67”的盆栽稻秧苗的叶子喷雾至滴流点。第二天，用宫部旋孢腔菌的孢子含水悬浮液接种植物。然后将测试植物置于22-24℃和95-99％相对大气湿度的气候室中6天。然后肉眼测定叶子上的侵染发展程度。
类似于实施例1进行评价。
表D-单一活性化合物
| 实施例 | 活性化合物 | 活性化合物在喷雾液体中的浓度[ppm] | 效力，相对于未处理对照的％ |
| 12 | 对照(未处理) | - | (90％侵染) |
| 13 | I | 164 | 5633 |
| 14 | II(肟菌酯) | 164 | 330 |
表E-本发明混合物
| 实施例 | 活性化合物的混合物浓度混合比 | 观察的效力 | 计算的效力*) |
| 15 | I+II16+4ppm4∶1 | 78 | 56 |
| 16 | I+II4+16ppm1∶4 | 83 | 53 |
*)使用Colby公式计算的效力
测试结果显示，对于所有的混合比而言，本发明混合物的观察效力显著高于用Colby公式预期的效力。
Claims (10)
1.一种杀真菌混合物，其以协同有效量包含如下化合物：
1)式I的三唑并嘧啶衍生物：
和
2)式II的肟菌酯：
2.一种杀真菌混合物，包含重量比为100∶1至1∶100的式I化合物和式II化合物。
3.一种杀真菌组合物，包含液体或固体载体以及权利要求1或2所要求的混合物。
4.一种防治稻病原性有害真菌的方法，该方法包括用有效量的权利要求1所述的化合物I和化合物II或权利要求3所要求的组合物处理真菌、其栖息地或要防止真菌侵袭的种子、土壤或植物。
5.如权利要求4所要求的方法，其中同时，即联合或分别施用或依次施用权利要求1所述的化合物I和II。
6.如权利要求4或5所要求的方法，其中权利要求1或2所要求的混合物或权利要求3所要求的组合物的施用量为5g/ha至2000g/ha。
7.如权利要求4或5所要求的方法，其中权利要求1或2所要求的混合物或权利要求3所要求的组合物的施用量为1-1000g/100kg种子。
8.如权利要求4-7中任何一项所要求的方法，其中防治有害真菌稻瘟病菌或宫部旋孢腔菌。
9.种子，以1-1000g/100kg的量包含权利要求1或2所要求的混合物。
10.权利要求1所述的化合物I和化合物II在制备适合防治稻病原体的组合物中的用途。
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