CN1833500A - 基于Prothioconazole并含有杀虫剂的杀真菌混合物 - Google Patents
基于Prothioconazole并含有杀虫剂的杀真菌混合物 Download PDFInfo
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- CN1833500A CN1833500A CNA200610072085XA CN200610072085A CN1833500A CN 1833500 A CN1833500 A CN 1833500A CN A200610072085X A CNA200610072085X A CN A200610072085XA CN 200610072085 A CN200610072085 A CN 200610072085A CN 1833500 A CN1833500 A CN 1833500A
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- prothioconazole
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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)
Abstract
本发明涉及杀真菌混合物，其包含协同有效量的如下组分：(1)式(I)的2－[2－(1－氯环丙基)－3－(2－氯苯基)－2－羟基丙基]－2，4－二氢－[1，2，4]－三唑－3－硫酮(Prothioconazole)或其盐或加合物和至少一种选自如下的杀虫剂：(2)式(II)的锐劲特，或(3)式(III)的毒死蜱，或(4)式(IV)的噻虫嗪。
Description
本申请是申请号为03805429.9的专利申请的分案申请，原申请的申请日为2003年03月04日，发明名称为“基于Prothioconazole并含有杀虫剂的杀真菌混合物”。
本发明涉及杀真菌混合物，其包含协同有效量的如下组分：
(1)式I的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2，4-二氢-[1，2，4]-三唑-3-硫酮(Prothioconazole)或其盐或加合物：
和至少一种选自如下的杀虫剂：
(2)式II的锐劲特：
或
(3)式III的毒死蜱：
或
(4)式IV的噻虫嗪(Thiamethoxam)：
此外，本发明涉及一种使用化合物I和化合物II、III或IV中的至少一种的混合物防治有害真菌的方法，化合物I、II、III和IV在制备该类混合物中的用途以及包含这些混合物的组合物。
式I化合物，即2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2，4-二氢-[1，2，4]-三唑-3-硫酮(Prothioconazole)已经由WO 96/16048已知。
WO 98/47367公开了Prothioconazole与大量其它杀真菌化合物的许多活性化合物组合。
式II的锐劲特描述于Pest.Man.(农药手册)，第12版(2000)，第413页中。
式III的毒死蜱也是已知的且描述于DE-A-1 445 659中。
最后，式IV的噻虫嗪同样是已知的且描述于EP-A 580553中。
本发明的目的是提供对有害真菌具有改进的活性且活性化合物的总施用量降低的混合物(协同增效混合物)，以降低施用率并改进已知化合物I、II、III和IV的活性谱。
我们发现该目的由开头所限定的Prothioconazole与至少一种杀虫剂的混合物实现。此外，我们发现同时施用，即一起施用或单独施用化合物I和至少一种其它化合物II、III或IV，或依次施用化合物I和化合物II、III或IV中的至少一种所提供的有害真菌防治作用比单独施用各化合物的可能作用要好。
式I的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2，4-二氢-[1，2，4]-三唑-3-硫酮由WO 96-16 048已知。该化合物可以下式的“硫酮”形式存在：
或以下式的互变异构“硫醇”形式存在：
为简单起见，在每种情况下仅给出“硫酮”形式。
式II的锐劲特描述于Pest.Man.，第12版(2000)，第413页中：
式III的毒死蜱描述于DE-A-1 445 659中：
式IV的噻虫嗪描述于EP-A-580 553中：
由于它们的氮原子呈碱性，化合物I能与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例是氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸，碳酸，硫酸，磷酸以及硝酸。
合适的有机酸例如是甲酸，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、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有带有1-20个碳原子的直链或支化烷基的磺酸)、芳基磺酸或芳基二磺酸(芳族基团如苯基和萘基，其带有一个或两个磺酸基)、烷基膦酸(具有带有1-20个碳原子的直链或支化烷基的膦酸)、芳基膦酸或芳基二膦酸(芳族基团如苯基和萘基，其带有一个或两个膦酸基团)，其中烷基或芳基可以带有其它取代基，例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
合适的金属离子尤其是第二主族元素的离子，尤其是钙和镁的离子；第三和第四主族元素的离子，尤其是铝、锡和铅的离子；第一至第八过渡族元素的离子，尤其是铬、锰、铁、钴、镍、铜和锌的离子；以及其它离子。特别优选第四周期过渡族元素的离子。金属可以各种它们可能呈现的化合价存在。
优选Prothioconazole与锐劲特的混合物。
此外，还优选Prothioconazole与毒死蜱的混合物。
还优选Prothioconazole与噻虫嗪的混合物。
还优选Prothioconazole上述杀虫剂中的两种的三组分混合物。
在制备混合物时，优选使用纯的活性化合物I、II、III和IV，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与化合物II、III和IV中的至少一种的混合物，或者同时，即联合或单独施用的化合物I和化合物II、III和IV中的至少一种对宽范围的植物病原性真菌具有显著的活性，所述真菌尤其选自子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)、藻菌纲(Phycomycetes)和半知菌纲(Deuteromycetes)真菌。它们中的一些起内吸作用并因此也可用作叶面和土壤作用杀真菌剂。
它们对在各种作物如棉花、蔬菜品种(例如黄瓜、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、水果品种、稻、黑麦、大豆、葡萄藤、小麦、观赏植物、甘蔗以及各种种子中防治大量真菌尤其重要。
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(Puccinia)属，棉花、稻和草坪中的丝核菌(Rhizoctonia)属，禾谷类和甘蔗中的黑粉菌(Ustilago)属，苹果中的苹果黑星菌(Venturiainaequalis)(黑星病)，禾谷类中的长蠕孢(Helminthosporium)属，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)(灰霉病)，花生中的落花生尾孢(Cercosporaarachidicola)，小麦和大麦中的眼斑病菌(Pseudocercosporellaherpotrichoides)，稻中的稻瘟病菌(Pyricularia oryzae)，土豆和西红柿中的致病疫霉(Phytophthora infestans)，葡萄藤中的葡萄生单轴霉(Plasmoparaviticola)，啤酒花和黄瓜中的假霜霉(Pseudoperonospora)属，蔬菜和水果中的链格孢(Alternaria)属，香蕉中的球腔菌(Mycosphaerella)属以及链孢霉(Fusarium)和轮枝孢(Verticillium)属。
此外，它们还可以用于保护材料(例如保护木材)以例如使其不受拟青霉(Paecilomyces variotii)的侵害。
化合物I和化合物II、III和IV中的至少一种可以同时，即一起或者单独施用，或依次施用，在单独施用下的顺序通常对防治结果没有任何影响。
化合物I和II通常以20∶1至1∶20，尤其是10∶1至1∶10，优选5∶1至1∶5的重量比施用。
化合物I和III通常以20∶1至1∶20，尤其是10∶1至1∶10，优选5∶1至1∶5的重量比施用。
化合物I和IV通常以20∶1至1∶20，尤其是10∶1至1∶10，优选5∶1至1∶5的重量比施用。
取决于所需效果的种类，本发明混合物的施用率尤其在农作物区域为0.01-8kg/ha，优选0.1-5kg/ha，尤其是0.1-3.0kg/ha。
化合物I的施用率为0.01-1kg/ha，优选0.05-0.5kg/ha，尤其是0.05-0.3kg/ha。
相应地，化合物II的施用率为0.01-1kg/ha，优选0.02-0.5kg/ha，尤其是0.05-0.3kg/ha。
相应地，化合物III的施用率为0.01-1kg/ha，优选0.02-0.5kg/ha，尤其是0.05-0.3kg/ha。
相应地，化合物IV的施用率为0.01-1kg/ha，优选0.02-0.5kg/ha，尤其是0.05-0.3kg/ha。
对于种子处理，该混合物的施用率通常为0.001-250g/kg种子，优选0.01-100g/kg种子，尤其是0.01-50g/kg种子。
若要防治植物病原性有害真菌，则化合物I和化合物II、III和IV中的至少一种的单独或联合施用或化合物I与化合物II、III或IV中的至少一种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。
本发明的杀真菌协同增效混合物或化合物I和化合物II、III和IV中的至少一种例如可以配制成即喷溶液、粉末和悬浮液形式或高度浓缩的水性、油性或其它悬浮液，分散体，乳液，油分散体，糊，粉剂，撒播用材料或粒剂的形式，且可以通过喷雾、雾化、撒粉、撒播或浇灌而施用。使用形式取决于意欲的目的；在任何情况下都应确保本发明混合物尽可能精细和均匀地分布。
配制剂通过本身已知的方式制备，例如通过加入溶剂和/或载体而制备。通常将惰性添加剂如乳化剂或分散剂与配制剂混合。
合适的表面活性剂为芳族磺酸如木质素-、苯酚-、萘-和二丁基萘磺酸以及脂肪酸的碱金属盐、碱土金属盐和铵盐，烷基-和烷基芳基磺酸盐，烷基、月桂基醚和脂肪醇硫酸盐以及硫酸化十六-、十七-和十八烷醇或脂肪醇乙二醇醚的盐，磺化萘及其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，聚氧乙烯辛基酚醚，乙氧基化异辛基-、辛基-或壬基酚，烷基酚或三丁基苯基聚乙二醇醚，烷基芳基聚醚醇，异十三烷醇，脂肪醇/氧化乙烯缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯，月桂醇聚乙二醇醚乙酸酯，山梨醇酯，木素亚硫酸盐废液或甲基纤维素。
粉末、撒播用材料和粉剂可以通过将化合物I和化合物II、III或IV中的至少一种或化合物I与化合物II、III或IV中的至少一种的混合物与固体载体混合或一起研磨而制备。
粒剂(例如包膜粒剂、浸渍粒剂或均相粒剂)通常通过将活性化合物与固体载体粘附而制备。
填料或固体载体例如为矿土如硅石、硅胶、硅酸盐、滑石、高岭土、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；纤维素粉或其它固体载体。
配制剂通常包含0.1-95重量％，优选0.5-90重量％的化合物I和化合物II、III或IV中的至少一种或化合物I与化合物II、III或IV中的至少一种的混合物。活性化合物以90-100％，优选95-100的纯度％(根据NMR光谱或HPLC)使用。
化合物I、II、III和IV，混合物或对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用化合物I与化合物II、III或IV中的至少一种处理有害真菌、其栖生地或想要防治它们的植物、种子、土壤、区域、材料或空间而施用。
施用可以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活性通过下列试验证实：
将活性化合物单独或一起在63重量％环己酮和27重量％乳化剂的混合物中配制成10％乳液，并用水稀释到所需浓度。
通过测定叶面积侵染百分数进行评价。将这些百分数转换成效力。使
用Abbot公式按如下计算效力(
W)：
W＝(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。
活性化合物的混合物的预期效力使用Colby公式[R.S.Colby，Weeds(杂草)
15，20-22(1967)]确定并与观测到的效力比较。
Colby公式：E＝x+y-x·y/100
E为使用浓度分别为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为活性化合物A以浓度a使用时的效力，以相对于未处理对照的％表示，
y为活性化合物B以浓度b使用时的效力，以相对于未处理对照的％表示。
应用实施例1：对由单丝壳(Snhaerotheca fuliginea)引起的黄瓜白粉病的保护活性
将栽培品种为“Chinese Snake”且处于子叶阶段的盆栽黄瓜秧苗的叶子用具有下述活性化合物浓度的含水悬浮液喷雾至滴流点。所述悬浮液或乳液由10％活性化合物在70％环己酮、20％湿润剂和10％乳化剂的混合物中的储备溶液制备。喷雾涂层干燥20小时后，将植物用黄瓜白粉病菌(Sphaerotheca fuliginea)的含水孢子悬浮液接种。然后将试验植物在20-24℃和60-80％相对大气湿度的温室中栽培7天。以子叶面积的侵染％肉眼确定白粉病发展程度。
将侵染叶面积的百分数的目测值转换成以相对于未处理对照的％表示的效力。效力为0表示侵染程度与未处理对照相同；效力为100表示0％侵染。活性化合物组合的预期效力使用前述Colby公式确定并与观测到的效力比较。
表1
| 活性化合物 | 活性化合物在喷雾液中的浓度，ppm | 效力，相对于未处理对照的％ |
| 对照(未处理) | (84％侵染) | 0 |
| 化合物I＝Prothioconazole | 0.250.060.015 | 500 |
| 化合物II＝锐劲特 | 10.25 | 00 |
| 0.060.015 | 00 | |
| 化合物III＝毒死蜱 | 0.250.060.015 | 000 |
| 化合物IV＝噻虫嗪 | 410.250.060.015 | 00000 |
表2
| 本发明的组合 | 观测到的效力 | 计算的效力*) |
| 化合物I＝Prothioconazole+化合物II＝锐劲特0.015+0.25ppm混合物1∶16 | 17 | 0 |
| 化合物I＝Prothioconazole+化合物II＝锐劲特0.25+1ppm混合物1∶4 | 64 | 5 |
| 化合物I＝Prothioconazole+化合物II＝锐劲特0.25+0.06ppm混合物4∶1 | 29 | 5 |
| 化合物I＝Prothioconazole+化合物II＝锐劲特0.25+0.015ppm混合物16∶1 | 64 | 5 |
| 化合物I＝Prothioconazole+化合物III＝毒死蜱0.015+0.25ppm混合物1∶16 | 17 | 0 |
| 化合物I＝Prothioconazole+化合物III＝毒死蜱0.06+0.25ppm混合物1∶4 | 29 | 0 |
| 化合物I＝Prothioconazole+化合物III＝毒死蜱0.25+0.06ppm混合物4∶1 | 29 | 5 |
| 化合物I＝Prothiocon azole+化合物III＝毒死蜱0.25+0.015ppm混合物16∶1 | 17 | 5 |
| 化合物I＝Prothioconazole+化合物IV＝噻虫嗪0.25+4ppm混合物1∶16 | 29 | 5 |
| 化合物I＝Prothioconazole+化合物IV＝噻虫嗪0.25+1ppm混合物1∶4 | 76 | 5 |
| 化合物I＝Prothioconazole+化合物IV＝噻虫嗪0.06+0.25ppm混合物1∶4 | 82 | 0 |
| 化合物I＝Prothioconazole+化合物IV＝噻虫嗪0.25+0.06ppm混合物4∶1 | 29 | 5 |
| 化合物I＝Prothioconazole+化合物IV＝噻虫嗪0.25+0.015ppm混合物16∶1 | 17 | 5 |
*)使用Colby公式计算的效力
试验结果表明在所有混合比下观测到的效力高于事先使用Colby公式计算的效力(来自Synerg 173.XLS)。
Claims (5)
1.一种杀真菌混合物，包含如下组分：
(1)式I的2-[2-(1-氯环丙基)-3-(2-氯苯基)-2-羟基丙基]-2，4-二氢-[1，2，4]-三唑-3-硫酮(Prothioconazole)或其盐或加合物：
和
(3)式III的毒死蜱：
其中式I的Prothioconazole与式III的毒死蜱的重量比为20∶1至1∶20。
2.一种防治有害真菌的方法，包括用如权利要求1所要求的杀真菌混合物处理有害真菌、其栖息地或需要防治它们的植物、种子、土壤、区域、材料或空间。
3.如权利要求2所要求的方法，其中将如权利要求1所述的式I化合物和如权利要求1所述的式III同时，即一起或单独，或依次施用。
4.如权利要求2或3所要求的方法，其中以0.01-8kg/ha的量施用如权利要求1所要求的杀真菌混合物或式I化合物和式III化合物。
5.一种杀真菌组合物，包含如权利要求1所要求的杀真菌混合物和固体或液体载体。
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103461362A (zh) * | 2013-09-05 | 2013-12-25 | 江苏龙灯化学有限公司 | 一种杀菌活性成分组合物 |
| CN104322558A (zh) * | 2014-09-30 | 2015-02-04 | 四川利尔作物科学有限公司 | 杀菌组合物及其应用 |
| CN107535518A (zh) * | 2016-06-28 | 2018-01-05 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
| CN107549190A (zh) * | 2016-07-01 | 2018-01-09 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
| CN107788009A (zh) * | 2016-08-29 | 2018-03-13 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL208689B1 (pl) * | 2002-03-08 | 2011-05-31 | Basf Ag | Mieszanina grzybobójcza na bazie protiokonazolu i insektycydu, sposób zwalczania szkodliwych grzybów i środek grzybobójczy |
| WO2005033079A1 (ja) * | 2003-09-30 | 2005-04-14 | Eisai Co., Ltd. | ヘテロ環化合物を含有する新規な抗真菌剤 |
| JPWO2006016548A1 (ja) * | 2004-08-09 | 2008-05-01 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環化合物を含有する新規な抗マラリア剤 |
| WO2006106711A1 (ja) | 2005-03-30 | 2006-10-12 | Eisai R & D Management Co., Ltd. | ピリジン誘導体を含有する抗真菌剤 |
| TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
| WO2007052479A1 (ja) * | 2005-11-04 | 2007-05-10 | Ngk Insulators, Ltd. | ハニカム構造体及びハニカム触媒体 |
| CN1330240C (zh) * | 2006-03-23 | 2007-08-08 | 浙江新安化工集团股份有限公司 | 杀虫组合物 |
| US8183264B2 (en) * | 2006-09-21 | 2012-05-22 | Eisai R&D Managment Co., Ltd. | Pyridine derivative substituted by heteroaryl ring, and antifungal agent comprising the same |
| CL2007003747A1 (es) * | 2006-12-22 | 2008-07-18 | Bayer Cropscience Ag | Composicion pesticida que comprende fosetil-al y un compuesto insecticida; y metodo para controlar hongos fitopatogenos o insecticidas daninos de las plantas, cultivos o semillas que comprende aplicar dicha composicion. |
| BR122019020347B1 (pt) * | 2007-02-06 | 2020-08-11 | Basf Se | Misturas, composição pesticida e métodos para controlar fungos nocivos fitopatogênicos, para proteger plantas do ataque ou infestação pelos insetos, acarídeos ou nematódeos e para proteger semente |
| CN101662939B (zh) | 2007-02-06 | 2015-11-25 | 利克斯特生物技术公司 | 氧杂双环庚烷和氧杂双环庚烯，它们的制备及用途 |
| AU2008244436B2 (en) | 2007-04-25 | 2013-03-14 | Basf Se | Fungicide mixtures |
| CN102702185A (zh) * | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
| TW200841879A (en) * | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
| EP2200439B1 (en) | 2007-10-01 | 2017-03-22 | Lixte Biotechnology, Inc. | Hdac inhibitors |
| US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
| EP2242370A2 (en) * | 2008-02-05 | 2010-10-27 | Basf Se | Pesticidal mixtures |
| EP2242372A2 (en) * | 2008-02-05 | 2010-10-27 | Basf Se | Pesticidal mixtures |
| JP5502854B2 (ja) * | 2008-05-08 | 2014-05-28 | ビーエーエスエフ ソシエタス・ヨーロピア | 菌類感染から大豆を保護する方法 |
| EA020599B1 (ru) * | 2008-07-04 | 2014-12-30 | Басф Се | Фунгицидные смеси, содержащие замещенные 1-метилпиразол-4-илкарбоксанилиды и абамектин |
| US8227473B2 (en) | 2008-08-01 | 2012-07-24 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes, their preparation and use |
| WO2010147612A1 (en) | 2009-06-18 | 2010-12-23 | Lixte Biotechnology, Inc. | Methods of modulating cell regulation by inhibiting p53 |
| US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
| MX2012000566A (es) * | 2009-07-16 | 2012-03-06 | Bayer Cropscience Ag | Combinaciones sinergicas de principios activos con feniltriazoles. |
| DK2667720T3 (da) * | 2011-01-28 | 2021-04-19 | Deepak Pranjivandas Shah | Pesticidsammensætning omfattende svovl, et fungicid og en agrokemisk excipiens |
| EP2484210A1 (en) | 2011-02-08 | 2012-08-08 | Basf Se | Pesticidal compositions |
| EP2983661B1 (en) | 2013-04-09 | 2024-05-29 | Lixte Biotechnology, Inc. | Formulations of oxabicycloheptanes and oxabicycloheptenes |
| WO2016034353A1 (en) * | 2014-09-03 | 2016-03-10 | Basf Se | Pesticidally active mixtures |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL125457C (zh) * | 1962-04-30 | 1965-07-12 | ||
| AU5042585A (en) * | 1984-12-10 | 1986-07-17 | Dow Chemical Company, The | Wood fungicides containing chlorpyrifos |
| DE3641554C2 (de) * | 1986-12-05 | 1995-04-06 | Solvay Werke Gmbh | Holzschutzmittel |
| TW240163B (en) * | 1992-07-22 | 1995-02-11 | Syngenta Participations Ag | Oxadiazine derivatives |
| US6022871A (en) * | 1992-07-22 | 2000-02-08 | Novartis Corporation | Oxadiazine derivatives |
| EP0705160A1 (de) * | 1993-06-21 | 1996-04-10 | Bayer Ag | Fungizide wirkstoffkombinationen |
| FR2712144B1 (fr) * | 1993-11-04 | 1997-07-18 | Rhone Poulenc Agrochimie | Association d'un fongicide à groupe azole avec un insecticide à groupe pyrazole, pyrrole ou phénylimidazole. |
| DE19528046A1 (de) * | 1994-11-21 | 1996-05-23 | Bayer Ag | Triazolyl-Derivate |
| EP0883345A1 (en) * | 1995-12-18 | 1998-12-16 | Novartis AG | Pesticidal composition |
| DE19548873A1 (de) * | 1995-12-27 | 1997-07-03 | Bayer Ag | Wirkstoffkombinationen |
| JP3810480B2 (ja) * | 1996-05-30 | 2006-08-16 | バイエルクロップサイエンス株式会社 | 殺菌殺虫組成物 |
| DE19716257A1 (de) * | 1997-04-18 | 1998-10-22 | Bayer Ag | Fungizide Wirkstoffkombination |
| WO1999027791A1 (en) * | 1997-11-28 | 1999-06-10 | Pugliese Peter T | Zwitterionic fatty acid compounds for anti-inflamation |
| CN1186602A (zh) * | 1998-01-19 | 1998-07-08 | 成都华西农药厂 | 毒死蜱与菊酯成分复配的杀虫农药 |
| BR9909002A (pt) | 1998-03-24 | 2000-11-28 | Basf Ag | Mistura fungicida e processo para controlar fungos nocivos |
| AU735903B2 (en) * | 1998-03-24 | 2001-07-19 | Basf Aktiengesellschaft | Fungicide mixtures based on tris(oxime ether) derivatives and insecticides |
| DE19829075A1 (de) * | 1998-06-17 | 1999-12-23 | Bayer Ag | Mittel zur Bekämpfung von Pflanzenschädlingen |
| DE19948590A1 (de) * | 1999-10-08 | 2001-04-12 | Bayer Ag | Wirkstoffkombination mit fungiziden und akariziden Eigenschaften |
| DE19956098A1 (de) * | 1999-11-22 | 2001-05-23 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE60214215T2 (de) * | 2001-09-21 | 2007-07-19 | E.I.Du Pont De Nemours And Company, Wilmington | Arthropodizide anthranilamide |
| PL208689B1 (pl) * | 2002-03-08 | 2011-05-31 | Basf Ag | Mieszanina grzybobójcza na bazie protiokonazolu i insektycydu, sposób zwalczania szkodliwych grzybów i środek grzybobójczy |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103461362A (zh) * | 2013-09-05 | 2013-12-25 | 江苏龙灯化学有限公司 | 一种杀菌活性成分组合物 |
| CN103461362B (zh) * | 2013-09-05 | 2014-12-24 | 江苏龙灯化学有限公司 | 一种杀菌活性成分组合物 |
| CN104322558A (zh) * | 2014-09-30 | 2015-02-04 | 四川利尔作物科学有限公司 | 杀菌组合物及其应用 |
| CN107535518A (zh) * | 2016-06-28 | 2018-01-05 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
| CN107549190A (zh) * | 2016-07-01 | 2018-01-09 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
| CN107788009A (zh) * | 2016-08-29 | 2018-03-13 | 四川利尔作物科学有限公司 | 种子处理剂组合物及其应用 |
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