CN1307877C - 包含咪唑菌酮和土菌消的杀真菌组合物 - Google Patents
包含咪唑菌酮和土菌消的杀真菌组合物 Download PDFInfo
- Publication number
- CN1307877C CN1307877C CNB2004800044841A CN200480004484A CN1307877C CN 1307877 C CN1307877 C CN 1307877C CN B2004800044841 A CNB2004800044841 A CN B2004800044841A CN 200480004484 A CN200480004484 A CN 200480004484A CN 1307877 C CN1307877 C CN 1307877C
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- Prior art keywords
- weight
- fenamidone
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- rice
- hydroxyisoxazole
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Abstract
本发明的目的是提供一种对于稻苗绵腐病明显有效的杀真菌组合物，它包含咪唑菌酮和土菌消作为活性成分。
Description
描述
本发明涉及一种用于农业和园艺的杀真菌组合物，特别涉及一种用于农业和园艺学的对于水稻植物呈现优良的真菌防治效果的杀真菌组合物，它可作为可选药剂用于防止由防效降低、尤其在甲霜灵(metalaxyl)抗性真菌种出现后引起的破坏。
到目前为止，为了在稻秧培养期间防治由腐霉菌(Pythium species)引起的稻苗绵腐病、防止幼苗发霉或保持幼苗在良好的生长条件下生长，一般广泛且普遍地使用土菌消(hymexazol)纯制剂或含有土菌消和甲霜灵作为活性成分的混合制剂，通过将它们灌溉入土壤或与土壤混合来施用。这两种化合物是已知的杀真菌活性成分。
另一方面，咪唑菌酮(fenamidone)本身是一种已知的杀真菌化合物。
关于它们各自制备方面的更多信息和方法记载于农药指南(PesticideManual)中。
甲霜灵是一种苯酰胺化合物，从它被商业化的早期阶段起就已经被植物病害专家以及从事水稻生产的农民所接受，它被接受的原因是：由于高渗透转移而形成好的治疗作用，以及由于高度影响新生叶子而形成长的后效应。因此，甲霜灵作为一种特殊的杀真菌剂被广泛地用于防治霜霉病、稻苗绵腐、特别是腐霉菌病害，以及由其它卵菌种引起的植物病害。
特别地，甲霜灵与土菌消的组合可以增强对稻苗绵腐病的防治作用以及对幼苗发霉的预防作用，因此已经广泛地被从事水稻生产的农民接受。然而，在率先将其商业化的欧洲国家中已经报导了抗性种的产生。在该报导之后，日本提出了一种建议，即用所谓的保护性杀真菌剂、使用次数、使用数量、喷雾持续期间在对该组合特别地加以限制。然而，在日本已经观察到马铃薯晚疫病和黄瓜霜霉病的出现。
另外，在甲霜灵的试用中，已经报导有草皮腐霉菌病(Pythium disease ofturf)病害的抗性种的出现，所述草皮腐霉菌病是土壤病症如稻苗绵腐病的同种型。
不久的将来，可以预期该种类型的抗性种将出现在稻苗绵腐病上，其是草皮腐霉菌病的同种型。因此，目前非常需要预先找出一种防范措施，以克服甲霜灵防治效力降低的问题。
本发明的目的是提供一种用于农业和园艺的杀真菌组合物，其呈现优良的性能，对于甲霜灵剂抗性种特别有效，并且在水稻幼苗培养期间，对于使幼苗在良好的条件下生长也呈现好的效力。
针对可满足上述需求的杀真菌剂的开发，本发明的发明人已经进行了透彻的研究。结果，本发明人成功地开发了本发明的杀真菌组合物，它呈现不同于甲霜灵剂的作用机制；并且对甲霜灵抗性种呈现优良的防治作用，特别是用于水稻，其采用与甲霜灵一样的低剂量，还可呈现一定程度的增效效果。
本发明关于一种用于农业和园艺的杀真菌组合物，其至少包括咪唑菌酮和土菌消作为活性成分。
已知咪唑菌酮是(S)-3，5-二氢-5-甲基-2-(甲硫基)-5-苯基-3-(苯基氨)-4H-咪唑-4-酮[通式(I)]，已知土菌消是5-甲基-3(2H)-异恶唑酮[通式(II)]
尽管本发明的组合物可以采用宽范围的咪唑菌酮和土菌消比例，所述咪唑菌酮和土菌消的重量比例优选在1/20至1/3的范围内，更优选在1/5至1/4的范围内。
如果可能，本发明的组合物可包括一种或多种其它活性成分，所述活性成分可选自除草剂、杀虫剂、杀真菌剂或者植物或昆虫生长调节剂。作为本发明的组合物中其它活性成分，优选的是杀真菌化合物，比如戊环唑，嘧菌酯，苯霜灵，苯菌灵，联苯，双苯三唑醇，灭瘟素-S，白克列(boscalid)，焦硼酸钠，糠菌唑，磺嘧菌灵，仲-丁胺，石硫合剂，敌菌丹，克菌丹，多菌灵，萎锈灵，环丙酰菌胺，灭螨猛，百菌清，乙菌利，氢氧化铜，辛酸铜，王铜，硫酸铜，氧化亚铜，清菌脲，环唑醇，环丙嘧啶，棉隆，双乙氧咪唑威，抑菌灵，双氯酚，双氯氰菌胺(diclocymet)，哒菌清，氯硝氨，乙霉威，噁醚唑，苯敌快，野燕枯，氟嘧菌胺，甲菌定，烯酰吗啉，烯唑醇，敌螨通，敌螨普，二苯胺，二噻农，吗菌灵，醋酸吗菌灵，多果定，克瘟散，氧唑菌，噻唑菌胺(ethaboxam)，乙菌定，促长啉，氯唑灵，噁唑酮菌，异嘧菌醇，分菌氰唑(fenbuconazole)，呋菌胺，环酰菌胺(fenhexamid)，拌种咯，氰菌胺(fenoxanil)，苯锈啶，丁苯吗啉，三苯锡基，毒菌锡，署瘟锡，福美铁，嘧菌腙，氟啶胺，氟噁菌，唑啶草(fluoroimide)，氟嘧菌酯(fluoxastrobin)，喹唑菌酮，氟硅唑，磺菌胺，氟酰胺，粉唑醇，灭菌丹，甲醛，三乙磷(fosetyl)，乙磷铝(fosetyl-aluminium)，麦穗宁，呋氨丙灵，呋吡唑灵，双胍盐，双胍辛醋酸盐，六氯苯，己唑醇，8-羟基喹啉硫酸盐，羟基喹啉硫酸钾，氰唑磺菌胺(cyazofamid)，烯菌灵硫酸盐(imazalilsulfate)，烯菌灵，酰胺唑，双胍辛胺(iminoctadine)，双胍辛醋酸盐，环戊唑醇，异稻瘟净，异丙定，丙森锌，稻瘟灵，春雷霉素，春雷霉素水合盐酸盐(kasugamycin hydrochloride hydrate)，亚胺菌，锰铜混剂，代森锰锌，代森锰，嘧菌胺，丙氧灭绣胺，升汞，氧化汞，甘汞，甲霜灵，精甲霜灵，威百亩(metam-sodium)，威百亩(metam)，环戊唑菌，磺菌威，异硫氰酸甲酯，代森联，叉氨苯酰胺，米多霉素，腈菌唑，代森钠，福美镍，异丙硝，氟苯嘧啶醇，异噻菌酮，甲呋酰胺，油酸，噁霜灵，喹啉铜，恶咪唑富马盐，氧化萎锈灵，稻瘟酯，戊菌唑，戊菌隆，五氯酚，五氯酚钠，月桂酸五氯苯酯(pentachlorophenyllaurate)，醋酸苯汞，2-苯基酚钠(sodium 2-phenylphenoxide)，2-联苯酚，苯酞，啶氧菌酯(picoxystrobin)，粉病灵，多抗霉素，例如多抗霉素B，多氧霉素(polyoxorim)，噻菌灵，丙氯灵，杀菌利，百维灵单盐酸盐，百维灵，丙环唑，prothioconazole，甲基代森锌，定菌磷，稗草丹(pyributicarb)，啶斑肟(pyrifenox)，嘧霉胺(pyrimethanil)，咯喹酮(pyroquilon)，苯氧喹啉(quinoxyfen)，五氯硝基苯(quinotzene)，婢草畏，螺噁茂胺，硫，重焦油，戊唑醇，四氯硝基苯，氟醚唑，涕必灵，溴氟唑菌，甲基托布津，福美双，甲基立枯磷，对甲抑菌灵，三唑酮，唑菌醇，唑菌嗪，三环唑，克啉菌，肟菌酯(trifloxystrobin)，氟菌唑，嗪氨灵，戊叉唑菌，有效霉素，烯菌酮，代森锌，福美锌，苯酰菌胺(zoxamide)，亚磷酸，唑菌胺酯(pyraclostrobin)或硅氟唑(simeconazole)。
在一种本发明的杀真菌剂的实际应用中，上述活性成分可以与已知的固体或液体载体、稀释剂、表面活性剂或其它辅助剂混合配制，制成一种常规的农用化学制剂，如粒剂、乳化或悬浮浓缩剂、可湿性粉剂、可流动剂、干燥可流动剂或其它适当的剂型。
作为用于配制本发明的组合物的固体载体，可以列举的比如以高岭石、蒙脱石、伊利石或polygroskite为代表的粘土，更具体地，可以列举的比如：叶蜡石、凹凸棒石(atapulgite)、海泡石、高岭石、膨润土、皂石、蛭石、云母、滑石。
可以列举的还比如：其它无机物质，比如石膏、碳酸钙、白云石、板状硅藻土、镁系化合物(magnesium line)、磷系化合物(phosphorus line)、沸石、无水硅石(silica anhydride)、合成硅酸钙；植物来源的有机物质如大豆粉、烟草粉、胡桃粉、小麦粉、木材粉、淀粉、结晶纤维素；合成或天然聚合物比如苯并呋喃树脂、石油树脂、醇酸树脂、聚氯乙烯、聚乙二醇类、酮树脂、酯树脂、苯乙烯树脂、达马树脂；蜡比如巴西棕榈蜡、蜂蜡或尿素等。
作为合适的液体载体，可以列举的比如：石蜡或环烷烃如煤油、矿物油、锭子油、白油；芳烃如二甲苯、乙苯、异丙基苯、甲基萘；氯代烃如三氯乙烯、一氯苯、邻-氯甲苯；醚类如二噁烷、四氢呋喃；酮类如甲基乙基酮、二异丁基酮、环己酮、苯乙酮、异佛尔酮；酯类如乙酸乙酯、乙酸戊酯、乙二醇乙酸酯、二乙二醇乙酸酯、马来酸二丁酯、丁二酸二乙酯；醇类如正己醇、乙二醇、二乙二醇、环己醇、苯甲醇；醚醇如乙二醇乙醚、乙二醇苯醚、二甘醇、乙醚、二甘醇丁醚；极性溶剂如二甲基甲酰胺、二甲基亚砜或水。
除了上述的物质，根据不同目的，还可使用表面活性剂、粘合剂以及其它辅助试剂，比如用于使活性成分乳化的表面活性剂、分散剂、润湿剂、扩展剂、集中剂、结合剂、破坏控制剂、活性成分稳定剂、流动性改进剂、抗腐蚀剂。
作为表面活性剂，可以应用任何类型的表面活性剂，比如非离子、阴离子、阳离子和两性表面活性剂。然而，通常可以应用非离子和/或阴离子表面活性剂。
作为合适的非离子表面活性剂的例子，可以列举的比如：环氧乙烷与高级醇如月桂醇、硬脂醇、油醇的聚合加成物；环氧乙烷与烷基苯酚如异辛基苯酚、壬基苯酚的聚合加成物；环氧乙烷与烷基萘酚如丁基萘酚、辛基萘酚的聚合加成物；环氧乙烷与高级脂肪酸如软脂酸、硬脂酸、油酸的聚合加成物；环氧乙烷与胺如月桂酰胺、硬脂酰胺的聚合加成物；环氧乙烷与高级醇的高级脂肪酸酯如脱水山梨醇(solbitan)的聚合加成物；环氧乙烷与环氧丙烷的嵌段共聚加成物。
作为合适的阴离子表面活性剂，可以列举的比如：烷基硫酸盐如月桂基硫酸钠、油醇的硫酸酯的胺盐；烷基磺酸盐如琥珀磺酸二辛酯钠、2-乙基己烯磺酸钠；芳基磺酸盐如异丙基萘磺酸钠、亚甲基二萘磺酸钠、木质素磺酸钠、月桂基苯磺酸钠。
此外，出于改进性能的目的，本发明的组合物可以与聚合物以及其它辅助剂组合使用，如酪蛋白、明胶、白蛋白、胶粘物、磺酸木质素、藻酸钠、阿拉伯树胶、黄原胶(xanthun gum)、羧甲基纤维素、甲基纤维素、羟乙基纤维素、聚乙烯醇醛、聚乙烯吡咯烷酮、多糖。
上述的载体和各种辅助剂可以单独地使用或结合其它物质使用，这取决于使用目的，比如考虑制剂类型或应用地点。
在如前所述制备的本发明的各种制剂中，活性成分的含量可以有很大的不同，这取决于制剂类型或应用地点。然而，活性成分的含量优选在0.01至99重量％的范围内，更优选在0.1至80重量％的范围内。
在一个具体的实施例中，根据本发明制备的可湿性粉剂通常包含比如：1至90重量％比例的活性成分，以及其余的固体载体和分散润湿剂。如必要，其中也可加入胶体保护剂、抗发泡剂。
颗粒制剂包含比如：0.01至70重量％比例的活性成分，其余的可以是固体载体或表面活性剂。所述活性成分可以与固体载体均一地混合，或者均一地被固定或吸收到固体载体颗粒的表面上。颗粒的直径大约在0.05至10mm的范围内，更优选地，在0.2至5mm的范围内。
根据本发明制备的可流动制剂通常包含比如：0.5至50重量％比例的活性成分，3至10重量％的分散润湿剂，以及其余的为水。如必要，其中也可加入胶体保护剂、防腐剂、抗发泡剂。
此外，本发明的组合物可以通过在施用时将活性成分咪唑菌酮和土菌消与前述的稀释剂、表面活性剂或其它辅助剂在容器中混合来制备。并且，咪唑菌酮和土菌消各自的纯制剂可以在需要的时候通过混合来施用。
如前所述制备的本发明的组合物的合适的施用剂量取决于天气状况、土壤状况、化学配方的形式、目标作物、施用次数、施用途径。
然而，通常基于活性成分的重量，施用剂量可以在每公顷0.01至1000g的范围内，优选在每公顷0.1至100g的范围内。此外，通过在本发明的组合物中加入其它药剂如杀虫剂、杀真菌剂、植物生长调节剂，可以制造一种节省人力的农用药剂。
本发明的组合物可以以治疗或预防的方法来防治植物病害，特别是防治腐霉菌属，尤其是稻苗绵腐菌(Pytium graminicola)。在本发明中，优选将所述方法用于对甲霜灵杀真菌活性成分呈现一定程度抗性的真菌菌株。
可用本发明的组合物来保护或治疗的植物优选的是谷类作物，特别地，本发明的组合物可用于防治水稻病害。
以下实施例以本发明的举例的方式给出，不以任何方式限制本发明。
制剂实施例1(粉末制剂)
| 咪唑菌酮 | 0.5重量％ |
| 土菌消(游离酸) | 4.0重量％ |
| Keiwa Clay Huhi | 95.5重量％ |
使用由富士粉剂有限公司(Fuji Power Company Ltd)制造的Equ SampleKII-1 Model均匀地研磨上述混合物，获得粉末制剂。Keiwa Clay Huhi是KeiwaRozai Company Ltd的一种商品。
制剂实施例2(可流动制剂)
(1)咪唑菌酮制浆的过程
| 咪唑菌酮 | 50.0重量％ |
| Tamol DN(由BASF制造) | 2.0重量％ |
| KP-1436(由Kao Company Ltd制造) | 0.5重量％ |
| Surphenol(由Nissin Chemical Industry Company Ltd制造) | 0.1重量％ |
| 水 | 47.4重量％ |
用0.1S Atoliter(由Mitsui Mining Company Ltd制造)在潮湿条件下均匀地研磨上述混合物，获得咪唑菌酮浆液(颗粒直径：D50：2.67μm)。
(2)溶解过程
| PittuCoal K-30(由第一工业有限公司[Daiichi Kogyo Company Ltd]制造) | 12.5重量％ |
| 丙二醇(由Go Do Solvent Company Ltd制造) | 62.5重量％ |
| 水 | 25.0重量％ |
将上述混合物混合，获得溶液。
(3)加强溶液粘度的过程
| KuniPia F(由Kuni Mine Chemical Industry Company Ltd) | 0.6重量％ |
| 丙二醇 | 5.0重量％ |
| 水 | 94.4重量％ |
将前述混合物混合，获得粘度加强的溶液。
(4)制备水性悬浮制剂的过程
| 过程(1)制备的咪唑菌酮浆液 | 8重量％ |
| 过程(2)制备的溶液 | 4重量％ |
| 过程(3)制备的粘性加强的溶液 | 25重量％ |
将60重量％的预先制备的土菌消(50重量％)铵溶液加入到上述的混合物中，通过加入水调节到100重量％。
从而，获得一种包含4.0重量％咪唑菌酮和30.0重量％土菌消的水性悬浮液。
制剂实施例3(可湿性粉剂)
| 咪唑菌酮 | 4重量％ |
| 土菌消(游离酸) | 30重量％ |
| CarpLex#80-D(由蓝野羲制药有限公司[ShionogiPharmaceutical Company Ltd]制造) | 10重量％ |
| GoSeNol GL 05(由日本合成化学品工业有限公司[NipponGosei Chemical Industry Company Ltd]制造) | 2重量％ |
| NewCoal 291PG(由日本乳化剂有限公司[Nippon NyukazaiCompany Ltd]制造) | 0.5重量％ |
| NeoGen Powder(由第一工业药物有限公司[Daiichi KogyoPharmaceutical Company Ltd]制造) | 5重量％ |
| Radiollite#20(由昭和化学工业有限公司[ShowaChemical Industry Company Ltd]制造) | 10重量％ |
| H Bihun(由Keiwa Rozai Company Ltd制造) | 38.5重量％ |
使用由Fuji Power Company Ltd制造的Equ Sample KII-1 Model均匀地研磨上述混合物，获得可湿性粉剂。
制剂实施例4(液体制剂)
| 咪唑菌酮 | 4重量％ |
| 土菌消(游离酸) | 30重量％ |
| N-甲基-2-吡咯烷酮(由Kurare Company Ltd制造) | 66重量％ |
采用钠沸石#200混合和过滤上述混合物，获得一种本发明的液体制剂。
试验实施例1：制剂实施例1的粉末制剂对于稻苗绵腐病的试验
预先在米糠培养基中培养稻苗绵腐病菌(Pythium graminicola)，将培养物与人工土壤混合，作为感染真菌的土壤用于试验。使用一种大小为水稻苗苗圃箱的1/15的塑料箱作为容器，一个箱子作为一小块地。
将每种预先确定的试验化合物的样品与感染真菌的土壤混合(播种前混合)，进行播种并用感染真菌的土壤覆盖。
将这些容器置于加湿的室内，30℃放置3天，接着在温度为10℃的室内放置3天，在室温房间放置2周后，评估产生的影响。
通过测定呈现稻苗绵腐病症状和褐腐病的幼苗的数量进行评估，并且防治效果通过一小块地中每100株苗中受感染的苗的数量来表示。
并且，增效效果基于Colby公式来确定，其用于计算活性成分的组合的增效和拮抗效果，公布在Weed 15(1967)20-22中。
当两种类型的除草剂进行组合时，Colby公式可以如下表示：
E＝X+Y-(XY/100)
其中，X表示有效剂量p的化合物A的防治效果(％)，Y表示有效剂量q的化合物B的防治效果(％)，并且E表示有效剂量p+q的化合物A+B的预期的防治效果(％)(理论值)。
当实际测出的值高于用Colby计算出的理论值时，可说明该组合产生的效果超过了累加所产生的效果，即该种组合呈现增效效果。
前述试验实施例的结果显示在以下的表1中。
| 样品 | 剂量(活性成分)以200个苗圃箱/ha计算 | 防治效果 | E |
| 咪唑菌酮 | 6g/ha | 90 | |
| 土菌消 | 48g/ha | 70 | |
| 咪唑菌酮+土菌消 | 6g+48g/ha | 100 | 97 |
表1：制剂实施例1的粉末制剂对于稻苗绵腐病的试验结果
从表1中可以清楚地发现，在使用制剂实施例1的粉末制剂的试验结果中，实际测出的值在理论值(E)之上。因此，可以说本发明的组合物在累加效果之上，即呈现增效效果。
试验实施例2：制剂实施例2的可流动(SC)制剂对于稻苗绵腐病的试验
该试验通过使用与试验实施例1相同的真菌感染土壤和容器进行。
作为化学制剂的应用，在播种后将预先制备的每种液体样品(500ml/苗圃箱)通过灌溉加入到土壤中，然后用感染真菌的土壤覆盖。
根据在试验实施例1中说明的方法完成试验过程及评估。结果显示在表2中。
| 样品 | 剂量(活性成分)以200个苗圃箱/ha计算 | 防治效果 | E |
| 咪唑菌酮 | 4g/ha | 90 | |
| 土菌消SC | 30g/ha | 75 | |
| 咪唑菌酮+土菌消SC | 4g+30g/ha | 100 | 97.5 |
表2：制剂实施例2的可流动制剂(SC)对于稻苗绵腐病的试验结果
从表2中可清楚地发现，在使用制剂实施例2的可流动制剂(SC)的试验结果中，实际测出的值在理论值(E)之上。因此，可以说本发明的组合物在累加效果之上，即呈现增效效果。
上面的试验实施例清楚地证明，本发明的组合物对于稻苗绵腐病呈现优良的防治效果。所述优良的效果是通过组合两种在作用机制上不同的杀真菌剂获得的，因此可以说，所述优良的效果归因于超过累加效果的增效效果。
Claims (9)
1.一种杀真菌组合物，包含咪唑菌酮和土菌消作为活性成分，所述组合物中咪唑菌酮和土菌消之间的重量比例在1/20至1/3之间。
2.如权利要求1所述的杀真菌组合物，其特征在于，所述的重量比例在1/15至1/4之间。
3.权利要求1所述的杀真菌组合物，其特征在于，所述组合物中还包含一种或多种用于配制的固体或液体载体，稀释剂，表面活性剂或其它辅助剂。
4.权利要求1所述的杀真菌组合物，其特征在于，所述活性成分的含量在0.1至80重量％范围内。
5.一种用于治疗或防治植物病害的方法，该方法使用权利要求1至4中任一项所述的组合物。
6.如权利要求5所述的方法，用于谷类作物的保护或治疗。
7.如权利要求6所述的方法，用于水稻病害的防治。
8.如权利要求5至7所述的方法，用于腐霉菌的防治。
9.如权利要求8所述的方法，用于稻苗绵腐病的防治。
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| JP2003042540A JP4399622B2 (ja) | 2003-02-20 | 2003-02-20 | 農園芸用殺菌剤組成物 |
| JP042540/2003 | 2003-02-20 |
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| JP4870443B2 (ja) * | 2006-02-15 | 2012-02-08 | 石原産業株式会社 | 植物病原菌防除用組成物及び植物病原菌の防除方法 |
| CL2007003743A1 (es) * | 2006-12-22 | 2008-07-11 | Bayer Cropscience Ag | Composicion que comprende fenamidona y un compuesto insecticida; y metodo para controlar de forma curativa o preventiva hongos fitopatogenos de cultivos e insectos. |
| CN102334497A (zh) * | 2011-05-21 | 2012-02-01 | 东莞市瑞德丰生物科技有限公司 | 一种防治植物病害的组合物 |
| EP2622961A1 (en) * | 2012-02-02 | 2013-08-07 | Bayer CropScience AG | Acive compound combinations |
| CN103478134B (zh) * | 2012-06-12 | 2016-02-17 | 陕西美邦农药有限公司 | 一种含咪唑菌酮的高效杀菌组合物 |
| CN103999861B (zh) * | 2013-04-07 | 2015-07-15 | 海南正业中农高科股份有限公司 | 含有环氟菌胺与咪唑菌酮的杀菌组合物 |
| CN106857551A (zh) * | 2015-12-11 | 2017-06-20 | 沈阳中化农药化工研发有限公司 | 一种用于防治土传病害杀菌组合物及其应用 |
| EP3954215A4 (en) * | 2019-04-05 | 2023-01-04 | Mitsui Chemicals Agro, Inc. | AGROCHEMICAL COMPOSITION WITH ENHANCED EFFICIENCY |
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| CN1153454A (zh) * | 1994-07-22 | 1997-07-02 | 罗纳-普朗克农业化学公司 | 含有2-咪唑啉-5-酮的杀真菌组合物 |
| CN1378782A (zh) * | 2002-01-08 | 2002-11-13 | 贵州大学 | 以恶霉灵原粉为主要原料配制的一组农用杀菌剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1153454A (zh) * | 1994-07-22 | 1997-07-02 | 罗纳-普朗克农业化学公司 | 含有2-咪唑啉-5-酮的杀真菌组合物 |
| CN1378782A (zh) * | 2002-01-08 | 2002-11-13 | 贵州大学 | 以恶霉灵原粉为主要原料配制的一组农用杀菌剂 |
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| 农用杀菌剂开发的新进展 刘长令，农药科学与管理，第21卷第2期 2000 * |
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| TW200500007A (en) | 2005-01-01 |
| ES2267047T3 (es) | 2007-03-01 |
| WO2004073401A3 (en) | 2004-11-25 |
| EP1596657B1 (en) | 2006-08-23 |
| JP4399622B2 (ja) | 2010-01-20 |
| KR20050101338A (ko) | 2005-10-21 |
| JP2004250378A (ja) | 2004-09-09 |
| DE602004002093D1 (de) | 2006-10-05 |
| HK1086988A1 (en) | 2006-10-06 |
| ATE336898T1 (de) | 2006-09-15 |
| CN1750760A (zh) | 2006-03-22 |
| WO2004073401A2 (en) | 2004-09-02 |
| EP1596657A2 (en) | 2005-11-23 |
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