CN1323586C - 杀真菌混合物 - Google Patents
杀真菌混合物 Download PDFInfo
- Publication number
- CN1323586C CN1323586C CNB2003801032527A CN200380103252A CN1323586C CN 1323586 C CN1323586 C CN 1323586C CN B2003801032527 A CNB2003801032527 A CN B2003801032527A CN 200380103252 A CN200380103252 A CN 200380103252A CN 1323586 C CN1323586 C CN 1323586C
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- carbamate
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- acid
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及包含协同有效量的如下化合物的杀真菌混合物：A)式(I)的三唑并嘧啶衍生物和B)式(II)的氨基甲酸酯类，其中n代表1或2且X代表卤素、烷基和卤代烷基，其中若n代表2则基团X可相互不同。本发明还涉及使用化合物I和II的混合物来防治病原性真菌的方法，包含所述混合物的试剂以及化合物I和II在生产该类混合物中的用途。
Description
本发明涉及杀真菌混合物，其包含协同有效量的如下化合物：A)式I的三唑并嘧啶衍生物：
和
B)式II的氨基甲酸酯：
其中n为1或2且X为卤素、C1-C4烷基或C1-C2卤代烷基，其中若n为2则基团X可不同。
此外，本发明还涉及使用化合物I和II的混合物来防治有害真菌的方法，包含这些化合物的组合物以及化合物I和化合物II在制备该类混合物中的用途。
式I化合物，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，其制备及其对抗有害真菌的作用由文献(WO 98/46607)已知。
式II的氨基甲酸酯属于嗜球果伞素活性化合物。其制备及其对抗有害真菌的作用同样已知(WO 93/15046和WO 96/01256)。
三唑并嘧啶与嗜球果伞素衍生物的混合物通常由EP-A 988 790已知。化合物I和II包括在该出版物的一般公开中；然而，式I的三唑并嘧啶或式II的氨基甲酸酯都未在EP-A 988 790中提及。
式II的氨基甲酸酯与其它活性化合物的混合物也是已知的(WO97/40673、WO 97/40676、WO 97/40684)。
该已知混合物的杀真菌活性并未完全令人满意。例如由EP-A 988 790已知的三唑并嘧啶活性化合物对防治卵菌纲(Oomycetes)的有害真菌的适用性有限。氨基甲酸酯II对抗卵菌纲的活性同样无法满足目前的要求。
为了降低施用率以及加宽活性谱，本发明的目的是提供具有改进的防治有害真菌，尤其是卵菌纲真菌的活性且活性化合物的施用总量降低的混合物(协同增效混合物)。
我们已发现该目的由开头所定义的混合物实现。此外我们还发现，与仅使用单独的化合物可能获得的防治相比，同时，即一起或单独施用化合物I和化合物II，或依次施用化合物I和化合物II对有害真菌提供了更好的防治。
化合物I和II的混合物，或者同时，即一起或单独施用的化合物I和II在对抗宽范围的植物病原性真菌，尤其是子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)、藻菌纲(Phycomycetes)和半知菌纲(Deuteromycetes)上协同作用并具有优异的活性。它们中的一些可内吸作用并因此也可用作叶面和土壤作用杀真菌剂。
它们对防治各种作物如棉花、蔬菜类(如黄瓜、豆类、西红柿、土豆和葫芦科植物)、大麦、禾草、燕麦、香蕉、咖啡、玉米、水果类、稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗以及大量种子中的大量真菌而言尤其重要。
它们特别适于防治下列植物病原性真菌：禾谷类中的禾白粉菌(Blumeria graminis)(白粉病)，葫芦科植物中的二孢白粉菌(Erysiphecichoracearum)和单丝壳(Sphaerotheca fuliginea)，苹果中的苹果白粉病菌(Podosphaera leucotricha)，葡萄藤中的葡萄钩丝壳(Uncinula necator)，禾谷类中的柄锈菌属(Puccinia)，棉花、稻和禾草中的丝核菌属(Rhizoctonia)，禾谷类和甘蔗中的黑粉菌属(Ustilago)，苹果中的苹果黑星菌(Venturiainaequalis)，禾谷类、稻和禾草中的平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera)，小麦中的小麦颖枯病菌(Septoria nodorum)，草莓、蔬菜、观赏植物和葡萄藤中的灰葡萄孢(Botrytis cinerea)，香蕉、花生和禾谷类中的球腔菌属(Mycosphaerella)，小麦和大麦中的小麦基腐病菌(Pseudocercosporella herpotrichoides)，稻中的稻瘟病菌(Pyricularia oryzae)，土豆和西红柿中的致病疫霉(Phytophthora infestans)，葫芦科植物和啤酒花中的假霜霉属(Pseudoperonospora)，葡萄藤中的葡萄生单轴霉(Plasmoparaviticola)，蔬菜和水果中的链格孢属(Alternaria)，以及镰孢霉属(Fusarium)和轮枝孢属(Verticillium)。
本发明混合物特别适于防治来自卵菌纲的有害真菌，尤其是各种蔬菜植物上的致病疫霉和葡萄藤上的葡萄生单轴霉。
此外，它们特别有利地适于防治禾谷类、蔬菜、水果、观赏植物和葡萄藤中的白粉病真菌和霜霉病真菌。
此外，它们可用于保护材料(例如保护木材)，例如对抗拟青霉(Paecilomyces variotii)。
式II尤其代表其中取代基的组合对应于下表中的一行的氨基甲酸酯：
| 编号 | Xn |
| II-1 | 2-F |
| II-2 | 3-F |
| II-3 | 4-F |
| II-4 | 2-Cl |
| II-5 | 3-Cl |
| II-6 | 4-Cl |
| II-7 | 2-Br |
| II-8 | 3-Br |
| II-9 | 4-Br |
| II-10 | 2-CH3 |
| II-11 | 3-CH3 |
| II-12 | 4-CH3 |
| II-13 | 2-CF3 |
| II-14 | 3-CF3 |
| II-15 | 4-CF3 |
| II-16 | 2，4-F2 |
| II-17 | 2，4-Cl2 |
| II-18 | 3，4-Cl2 |
| II-19 | 2-Cl，4-CH3 |
| II-20 | 3-Cl，4-CH3 |
优选其中X为氟、氯或甲基且位于对位的式IIa化合物；这些化合物如式IIa所示：
优选其中X为氟、氯、甲基或三氟甲基的式IIa化合物。特别优选化合物II-3、II-6、II-12和II-17，尤其是II-6(通用名：百克敏(pyraclostrobin))。
由于其氮原子的碱性特性，化合物I和II可与无机酸或有机酸或与金属离子形成盐或加合物。
无机酸的实例为氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸，硫酸，磷酸和硝酸。
合适的有机酸例如为甲酸，碳酸和链烷酸如乙酸、三氟乙酸、三氯乙酸和丙酸，以及还有羟基乙酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸或2-乙酸基苯甲酸等。
合适的金属离子尤其是第一至第八过渡族元素，尤其是铬、锰、铁、钴、镍、铜、锌的离子；还有第二主族元素，尤其是钙和镁的离子；以及第三和第四主族元素，尤其是铝、锡和铅的离子。金属可以它们可能呈现的各种化合价存在。
当制备该混合物时，优选使用纯的活性化合物I和II，可以向其中加入其它对抗有害真菌或其它害虫如昆虫、蜘蛛或线虫的活性化合物，或具有除草作用或生长调节作用的活性化合物或肥料。
化合物I和II可以同时，即一起或单独，或依次施用，在单独施用的情况下顺序通常对防治措施的结果没有任何影响。
化合物I和II通常以100∶1-1∶100，尤其是20∶1-1∶20，优选10∶1-1∶10的重量比施用。
取决于所需的效果，本发明混合物的施用率尤其在农业种植区域为5-2000g/ha，优选50-1500g/ha，尤其是50-750g/ha。
这里化合物I的施用率为1g-1kg/ha，优选10-900g/ha，尤其是20-750g/ha。
相应地，化合物II的施用率为1g-1kg/ha，优选10-750g/ha，尤其是20-500g/ha。
处理种子时，混合物的施用率通常为0.1-1000g/100kg种子，优选0.1-200g/100kg，尤其是1-100g/100kg。
若要防治植物病原性有害真菌，则化合物I和II的单独或联合施用或化合物I和II的混合物的施用通过在植物播种之前或之后或在植物出苗之前或之后对种子、植物或土壤喷雾或撒粉而进行。
可将本发明的杀真菌协同混合物或化合物I和II例如配制为可直接喷雾溶液、粉末和悬浮液或高度浓缩的水性、油性或其它悬浮液、分散体、乳液、油分散体、糊、粉剂、撒播用组合物或颗粒，且可通过喷雾、雾化、撒粉、撒播或浇水等方式施用。施用形式取决于特定目的；在各种情况下，应确保本发明混合物尽可能精细且均匀地分布。
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/助剂主要为：
-水、芳族溶剂(如Solvesso产品、二甲苯)、石蜡(如矿物馏分)、醇类(如甲醇、丁醇、戊醇、苯甲醇)、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)、二醇、脂肪酸二甲酰胺、脂肪酸及脂肪酸酯。原则上，还可使用溶剂混合物，
-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-甲基吡咯烷酮或水。
粉末、撒播用材料和可撒粉产品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)可以通过使活性化合物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，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。
该配制剂通常包含0.01-95重量％，优选0.1-90重量％的活性化合物。该活性化合物以90-100％，优选95-100％的纯度(根据NMR光谱)使用。
下列为配制剂实例：
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)可分散浓缩物(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(在各情况下浓度为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(在各情况下浓度为5％)。借助乳化器(Ultraturvax)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-定子研磨机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.不经稀释即可施用的产品
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。这得到不经稀释即可施用的颗粒。
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。这得到不经稀释即可施用的产品。
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(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒)，借助喷雾、雾化、撒粉、撒播或浇注来使用。使用形式完全取决于意欲的目的；意欲在各种情况下确保本发明活性化合物的最佳可能分布。
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，该浓缩物适于用水稀释。
即用制剂中的活性化合物浓度可在较宽范围内变化。通常为0.0001-10％，优选0.01-1％。
活性化合物也可成功用于超低容量法(ULV)中，可以施用包含超过95重量％活性化合物的配制剂，或甚至施用不含添加剂的活性化合物。
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化合物中，若合适的话，恰在紧邻使用前加入(桶混合)。这些试剂可与本发明试剂以1∶10-10∶1的重量比混合。
化合物I和II、混合物或相应的配制剂通过用杀真菌有效量的混合物或在单独施用的情况下化合物I和II来处理有害真菌、其栖息地或要防治它们的植物、种子、土壤、区域、材料或空间而施用。
施用可在有害真菌侵染之前或之后进行。
应用实施例
本发明混合物的协同增效作用可通过下列实验说明：
将单独或联合的活性化合物制备成在63重量％环己酮和27重量％乳化剂的混合物中的10％乳液并用水稀释至所需浓度。
通过测定叶面积侵染百分数进行评价。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对照植物的侵染水平；效力为100表示处理植物未受侵染。
活性化合物混合物的预期效力使用Colby公式[R.S.Colby，杂草(Weeds)15，20-22(1967)]确定并与观察到的效力比较：
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，以未处理对照的％表示。
应用实施例-对抗由葡萄生单轴霉(Plasmopara viticola)引起的葡萄藤霜霉病的活性
将栽培品种为“Müller-Thurgau”的盆栽葡萄藤的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。悬浮液或乳液由在由70重量％环己酮、20重量％湿润剂和10重量％乳化剂组成的混合物中包含10％活性化合物的储液制备。第二天，用葡萄生单轴霉的游动孢子含水悬浮液接种叶子下侧。然后将葡萄藤首先置于24℃的水蒸气饱和室中48小时并随后置于20-30℃的温室中5天。此阶段之后，将植物再次置于湿室中16小时以促进孢囊柄萌发。然后肉眼测定叶子下侧病害的发展程度。
表A-单独的活性化合物
| 试验编号 | 活性化合物 | 活性化合物在喷雾液中的浓度[ppm] | 效力，未处理对照的％ |
| 1 | 对照(未处理) | (70％侵染) | - |
| 2 | I | 410.25 | 2900 |
| 3 | II-6(百克敏) | 1 | 29 |
表B-本发明混合物
| 试验编号 | 活性化合物的混合物/浓度/混合比 | 观察到的效力 | 计算的效力*) |
| 4 | I+II-64+1ppm4∶1 | 100 | 49 |
| 5 | I+II-61+1ppm1∶1 | 100 | 29 |
| 6 | I+II-60.25+1ppm1∶4 | 100 | 29 |
*)使用Colby公式计算的效力
试验结果表明对所有混合比而言，对本发明混合物观察到的效力高于使用Colby公式预先计算的效力。
Claims (9)
1.一种杀真菌混合物，包含如下化合物：
A)式I的三唑并嘧啶衍生物：
和
B)式II的氨基甲酸酯：
其中n为1或2且X为卤素、C1-C4烷基或C1-C2卤代烷基，其中若n为2则基团X可不同，
其中三唑并嘧啶I与式II的氨基甲酸酯的重量比为100∶1-1∶100。
2.如权利要求1所要求的杀真菌混合物，其中氨基甲酸酯II对应于式IIa：
其中X为氟、氯或甲基。
3.如权利要求1或2所要求的杀真菌混合物，包含化合物II-6作为氨基甲酸酯II：
4.一种杀真菌组合物，包含如权利要求1-3中任一项所要求的杀真菌混合物和固体或液体载体。
5.一种防治植物病原性有害真菌的方法，包括用如权利要求1所定义的式I三唑并嘧啶衍生物和如权利要求1-3中任一项所定义的式II氨基甲酸酯或者用如权利要求4所要求的组合物处理有害真菌、其栖息地或要防治它们的植物、种子、土壤、区域、材料或空间，其中前述式I三唑并嘧啶衍生物与式II氨基甲酸酯的重量比为100∶1-1∶100，以及式I三唑并嘧啶衍生物的施用率为1g-1kg/ha，和式II氨基甲酸酯的施用率为1g-1kg/ha。
6.如权利要求5所要求的方法，其中如权利要求1所定义的式I的三唑并嘧啶衍生物和如权利要求1所定义的式II的氨基甲酸酯同时，即一起或单独，或依次施用。
7.如权利要求5或6所要求的方法，其中如权利要求1-3中任一项所要求的混合物的施用量为5-2000g/ha。
8.如权利要求5或6所要求的方法，其中如权利要求1-3中任一项所要求的混合物的施用量为1-1000g/100kg种子。
9.一种制备如权利要求4所要求的杀真菌组合物的方法，包括将如权利要求1-3中任一项所定义的式I和式II的化合物与溶剂和/或载体混合。
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| WO1998046607A1 (en) * | 1997-04-14 | 1998-10-22 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
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| CZ295558B6 (cs) * | 2001-04-11 | 2005-08-17 | Basf Aktiengesellschaft | 5-Halogen-6-fenyl-7-fluoralkylamino-triazolopyrimidiny, způsob jejich přípravy a prostředek pro potírání fytopatogenních hub |
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- 2003-11-14 PL PL376885A patent/PL376885A1/pl unknown
- 2003-11-14 BR BR0316237-0A patent/BR0316237A/pt not_active IP Right Cessation
- 2003-11-14 CN CNB2003801032527A patent/CN1323586C/zh not_active Expired - Fee Related
- 2003-11-14 NZ NZ540413A patent/NZ540413A/en unknown
- 2003-11-14 CA CA002505481A patent/CA2505481A1/en not_active Abandoned
- 2003-11-14 OA OA1200500139A patent/OA12957A/en unknown
- 2003-11-14 US US10/532,756 patent/US20050288309A1/en not_active Abandoned
- 2003-11-14 AU AU2003293690A patent/AU2003293690A1/en not_active Abandoned
- 2003-11-14 RS YUP-2005/0359A patent/RS20050359A/sr unknown
- 2003-11-17 TW TW092132379A patent/TW200503622A/zh unknown
- 2003-11-17 AR ARP030104241A patent/AR042056A1/es not_active Application Discontinuation
- 2003-11-17 AR ARP030104239A patent/AR042201A1/es unknown
-
2005
- 2005-04-20 NO NO20051924A patent/NO20051924L/no not_active Application Discontinuation
- 2005-04-26 EC EC2005005759A patent/ECSP055759A/es unknown
- 2005-05-03 EG EGNA2005000187 patent/EG23742A/xx active
- 2005-05-30 MA MA28305A patent/MA27495A1/fr unknown
- 2005-06-14 ZA ZA200504839A patent/ZA200504839B/en unknown
- 2005-06-15 HR HR20050551A patent/HRP20050551A2/xx not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996001256A1 (de) * | 1994-07-06 | 1996-01-18 | Basf Aktiengesellschaft | 2-[(dihydro)pyrazolyl-3'-oxymethylen]-anilide als schädlingsbekämpfungsmittel und fungizide |
| WO1998046607A1 (en) * | 1997-04-14 | 1998-10-22 | American Cyanamid Company | Fungicidal trifluorophenyl-triazolopyrimidines |
| EP0988790A1 (en) * | 1998-09-25 | 2000-03-29 | American Cyanamid Company | Fungicidal mixtures |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2505481A1 (en) | 2004-06-03 |
| AP2005003313A0 (en) | 2005-06-30 |
| TW200503622A (en) | 2005-02-01 |
| OA12957A (en) | 2006-10-13 |
| HRP20050551A2 (en) | 2005-08-31 |
| AU2003293690A1 (en) | 2004-06-15 |
| JP2006506426A (ja) | 2006-02-23 |
| PL376885A1 (pl) | 2006-01-09 |
| MXPA05004369A (es) | 2005-07-05 |
| US20050288309A1 (en) | 2005-12-29 |
| AR042056A1 (es) | 2005-06-08 |
| BR0316237A (pt) | 2005-10-11 |
| EA007925B1 (ru) | 2007-02-27 |
| RS20050359A (en) | 2007-11-15 |
| NO20051924L (no) | 2005-06-14 |
| NZ540413A (en) | 2007-04-27 |
| KR20050086632A (ko) | 2005-08-30 |
| CN1711023A (zh) | 2005-12-21 |
| UA78622C2 (en) | 2007-04-10 |
| AR042201A1 (es) | 2005-06-15 |
| ECSP055759A (es) | 2006-04-19 |
| EG23742A (en) | 2007-07-29 |
| MA27495A1 (fr) | 2005-08-01 |
| WO2004045289A1 (de) | 2004-06-03 |
| EA200500705A1 (ru) | 2005-12-29 |
| EP1562427A1 (de) | 2005-08-17 |
| ZA200504839B (en) | 2006-08-30 |
| KR100716080B1 (ko) | 2007-05-08 |
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