CN105829306A - 2-{3-[2-(1-{[3,5-双(二氟甲基)-1h-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的新晶形 - Google Patents
2-{3-[2-(1-{[3,5-双(二氟甲基)-1h-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的新晶形 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
- A01C1/06—Coating or dressing seed
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Soil Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及2{3[2(1{[3,5双(二氟甲基)1H吡唑1基]乙酰基}哌啶4基)1,3噻唑4基]4,5二氢1,2噁唑5基}3氯苯基甲磺酸酯的新晶形,其制备方法及其在农业化学制剂中的用途。
Description
本发明涉及2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(参见图1)的新晶形,涉及制备该新晶形的方法,涉及用于制备稳定施用形式的有利的用途,以及涉及其用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的用途。
2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯
化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯以及制备该化合物的方法是已知的。还已知该化合物具有杀真菌作用。因此,例如WO 2012/025557第一次记载了该化合物的制备及其用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的用途。
此外,已知所述化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯可以与其他杀真菌剂的混合物来使用:WO 2013/127704。
WO 2012/025557中的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯为无定形固体的形式。其可以固体溶解于其中的制剂来使用,例如乳液浓缩剂(EC),也可以活性成分仍然以固体形式存在于其中的制剂(固体制剂)来使用。其为例如颗粒剂、胶囊颗粒剂、片剂、水分散性颗粒剂、水分散性片剂、水分散性粉剂或用于处理种子的水分散性粉剂、粉尘制剂(dust formulation)、活性成分以分散形式存在于其中的制剂(例如悬浮浓缩剂(SC)、油基悬浮浓缩剂、悬浮乳剂或用于处理种子的悬浮浓缩剂)。
原则上,固体制剂因其具有非常良好的存贮稳定性而具有巨大的经济意义。然而,这只是在活性成分是以无定形形式存在并因此未处于热力学最稳定的变型下的情况。
由于对现代作物保护组合物的生态和经济要求持续提高(例如就活性谱、活性和施用率而言),因此期望活性成分2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯除了存在无定形形式以外,还存在其他变型,所述变型在固体制剂中与已知的相比在至少部分领域中具有优势。
出人意料地,现已发现2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的一种新晶形,其避免了固体制剂中的上述存贮稳定性的缺点,并且在固体制剂中与无定形形式相比具有改进的杀真菌活性。
因此本发明涉及化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的新晶形,其特征在于该化合物在25℃下且使用Cu-Kα辐射的X-射线粉末衍射(见图2)具有至少3个,特别是至少4或6个且优选所有的下列2Θ(2theta)值(表1):
表1:
除了2Θ值,所述新晶形还具有列于表2中的晶格面间距“d”。
表2:化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的新晶形的2Θ值和晶格面间距“d”,通过X-射线粉末衍射法测定。
出人意料地,已发现所述新晶形的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯就经济相关的用途而言是热力学足够稳定的,并且即使在长期储存时也不会转化成其他形式。
这使得能够制备悬浮浓缩剂、油基悬浮浓缩剂以及,例如水分散性颗粒剂以及用于种子处理的类似的制剂。
所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯,基于其稳定性,极其适用于制备用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的组合物。因此,本发明还提供用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的组合物,其只单独地包含所述新晶形或以与助剂和载体的混合物包含所述新晶形,以及以与其他活性成分的混合物包含所述新晶形。
本发明还包括包含所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的组合物。优选组合物包含小于20重量%的新固体形式,特别优选小于15重量%,非常特别优选小于10重量%,特别优选小于5重量%,且最优选小于4、3、2或1重量%的新晶形。术语“组合物”还包括制剂和使用形式。
此外,本发明还涉及制备用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的组合物的方法,其使用了所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯。通过使用所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯,包含化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的制剂的安全性提高,从而降低了错误剂量的风险。
使用合适的助剂和载体或溶剂,可以已知的方式将所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯转化成常规制剂,如悬浮浓缩剂、油基悬浮浓缩剂、胶体浓缩剂、分散性浓缩剂、可乳化浓缩剂(乳液浓缩剂)、乳液拌种剂(dressings)、悬浮拌种剂、颗粒剂、微颗粒剂、悬浮乳剂、水溶性颗粒剂、水溶性浓缩剂和水分散剂颗粒剂,以及相应的即用型制剂。就此而言,活性化合物的存在的浓度应为总混合物的约0.0001至90重量%,即足以达到所需剂量水平的量。所述制剂通过例如将所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯与水、溶剂和/或载体混合而制备,如果合适的话使用乳化剂和/或分散剂、和/或其他助剂,例如渗透剂。
在悬浮浓缩剂(包括用于种子处理的悬浮浓缩剂)的制备中,除活性成分和增充剂(水、溶剂或油)之外通常还加入其他助剂。润湿剂用于润湿连续相中的活性成分,分散剂用于使液相的悬浮液稳定,乳化剂用于使包含溶剂或油的悬浮浓缩剂的非水相乳化。如果需要,掺入防冻剂、杀生物剂、增稠剂、着色剂、铺展剂(spreading agent)和/或渗透剂。
所述新的固体化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯通过下文所述的方法获得。化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯按照例如WO2012/025557中所述的方法制备。由此获得的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯为无定形态。
为了制备本发明的化合物,在至少50℃温度下,优选至少80℃下,将无定形2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯悬浮于溶剂或溶剂混合物中,然后缓慢冷却直至析出所需的晶体。所用溶剂的量的选择为使得混合物在结晶过程中保持易于搅拌的状态。
线性地或分步地进行缓慢冷却。优选地,线性地进行冷却,其中在将其进一步冷却直至析出所需晶体之前,在特定的温度下,优选在约20℃下将结晶溶液搅拌数小时,优选5至25小时,特别优选15至20小时,非常特别优选16至17小时。
任选地将晶种加入悬浮液中以促进结晶。原则上晶种的添加可在搅拌过程中进行。
合适的溶剂为卤代烃(例如氯苯、溴苯、二氯苯、氯甲苯、三氯苯),醚(例如乙基丙基醚、甲基叔丁基醚、正丁基醚、苯甲醚、苯乙醚、环己基甲基醚、二甲醚、二乙醚、二甲基二醇、二苯基醚、二丙基醚、二异丙基醚、二正丁基醚、二异丁基醚、二异戊基醚、乙二醇二甲醚、异丙基乙基醚、甲基叔丁基醚、四氢呋喃、甲基四氢呋喃、二氧六环、二氯二乙醚、甲基-THF以及环氧乙烷和/或环氧丙烷的聚醚),硝基烃(例如硝基甲烷、硝基乙烷、硝基丙烷、硝基苯、氯硝基苯、邻-硝基甲苯),脂族、环脂族或芳族烃(例如戊烷、正己烷、正庚烷、正辛烷、壬烷(例如具有沸点在例如40℃至250℃范围的组分的石油溶剂油)、对异丙基甲苯、沸程为70℃至190℃的石油馏分、环己烷、甲基环己烷、石油醚、轻石油、辛烷、苯、甲苯、二甲苯),酯(例如丙二酸酯、乙酸正丁基酯(乙酸正丁酯)、乙酸甲酯、乙酸乙酯、乙酸异丁酯、碳酸二甲酯、碳酸二乙酯、碳酸二丁酯、碳酸亚乙酯);以及脂族醇(例如甲醇、乙醇、正丙醇和异丙醇和正丁醇、叔戊醇)。优选的溶剂为醚,芳族烃(如苯、甲苯、二甲苯、氯苯),酯和脂族醇及其混合物。特别优选的溶剂或溶剂混合物为异丙醇、甲苯、甲基-THF、碳酸二乙酯、氯苯、乙酸正丁酯和乙酸异丁酯、正丁醇、乙醇、丙二酸乙酯、甲基叔丁基醚,以及甲苯和丁醇的混合物、甲苯和乙酸正丁酯的混合物、丙二酸乙酯和甲基叔丁基醚的混合物、以及乙酸丁酯和甲基叔丁基醚的混合物。也可能为具有2个以上组分的混合物。
除上述制剂以外,还可将所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯转化成其他制剂。这些制剂为,例如溶液剂、乳剂、可湿性粉剂、水基和油基悬浮剂、粉剂、尘剂、糊剂、可溶性粉剂、可溶性颗粒剂、用于撒播的颗粒剂、悬浮乳剂浓缩剂、用活性成分浸渍的天然化合物、用活性成分浸渍的合成物质、肥料以及于聚合物质中的微胶囊。本发明优选固体制剂。
所述制剂以已知方式制备,例如通过将活性成分与增充剂(即液体溶剂和/或固体载体)混合,任选地使用表面活性剂(即润湿剂、乳化剂、分散剂和/或消泡剂)。所述制剂在合适的设备中制备或者在施用之前或施用过程中制备。
所用的助剂可为适用于向组合物本身和/或源自其的制剂(例如喷雾液、拌种剂)赋予特别的特性的那些物质,例如特定的技术特性和/或特别的生物特性。通常的助剂包括:增充剂、溶剂和载体。
合适的增充剂为,例如水,例如下述类别的极性和非极性有机化学液体,例如芳族和非芳族烃(如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(其中,如果合适的话也可为取代的、醚化的和/或酯化的)、酮(如环己酮)、酯(包括脂肪和油)和(聚)醚、未取代和取代的胺、酰胺、内酰胺(如N-烷基吡咯烷酮)和内酯、砜和亚砜(如二甲亚砜)。
如果所用的增充剂为水,则还可使用例如有机溶剂作为助溶剂。有用的液体溶剂基本上包括:芳族化合物(例如二甲苯、甲苯或烷基萘),脂族烃或石蜡(例如矿物油馏分、矿物油和植物油),醇及其醚和酯,酮(例如甲基乙基酮、甲基异丁基酮或环己酮),强极性溶剂(例如N-甲基吡咯烷酮、二甲亚砜、以及水)。
根据本发明,载体为天然或合成的、有机或无机物质,其可为固体或液体,并且活性成分可与其混合或键合以具有更好的适用性,特别是对植物或植物部位或种子的施用。所述固体或液体载体通常是惰性的且应可用于农业。
合适的固体或液体载体为:
例如铵盐和磨碎的天然矿物(如高岭土、粘土、滑石、白垩、石英、凹凸棒石(attapulgite)、蒙脱石(montmorillonite)或硅藻土)和合成岩石粉末(如细碎的二氧化硅、氧化铝和硅酸盐);用于颗粒剂的合适的固体载体为:例如粉碎并分级的天然岩石(如方解石、大理石、砂、浮石、海泡石、白云石),以及合成的无机和有机粉末的颗粒,以及有机材料(如纸、木屑、椰壳、玉米穗轴和烟草茎)的颗粒;合适的乳化剂和/或发泡剂为:例如,非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚(例如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白水解物;合适的分散剂为非离子和/或离子物质,例如选自下述类别:脂肪醇-POE和/或POP醚、酸和/或POP POE醚、烷基芳基和/或POPPOE醚、脂肪和/或POP POE加合物、POE-和/或POP-多元醇混合物、POE-和/或POP-脱水山梨糖醇或-糖加合物、烷基或芳基硫酸盐、烷基或芳基磺酸盐以及烷基或芳基磷酸盐或相应的PO-醚加合物。另外,也可使用木质素及其磺酸衍生物、未改性和改性的纤维素、芳族和/或脂族磺酸及其与甲醛的加合物。
在所述制剂中,可使用增粘剂(例如羧甲基纤维素),粉末、颗粒或胶乳形式的天然和合成的聚合物(例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯),或天然磷脂(例如脑磷脂及卵磷脂),以及合成磷脂。
可使用染料如无机颜料,如氧化铁、氧化钛和普鲁士蓝;以及有机染料,例如茜素染料、偶氮染料和金属酞菁染料;以及微量营养素,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
其他的添加剂可为香料、矿物或植物油、任选改性的油、蜡和营养素(包括微量营养素)(例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐)。
还可存在稳定剂,例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或提高化学和/或物理稳定性的其它试剂。
由制剂制备的使用形式的活性成分含量可在宽范围内变化。使用形式的活性成分浓度范围为0.00000001至97重量%的活性成分,优选0.0000001至97重量%,特别优选0.000001至83重量%或0.000001至5重量%,且非常特别优选0.0001至1重量%。
本发明的所述新晶形的化合物2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯,加上良好的植物相容性、有利的温血动物毒性和良好的环境耐受性,适合用于保护植物和植物器官,用于提高采收产量、改善采收产品的品质以及用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌。可根据本发明处理的真菌病害的病原体的非限制性实例包括:
由白粉病病原体引起的病害,例如,布氏白粉菌属(Blumeria),例如禾本科布氏白粉菌(Blumeria graminis);叉丝单囊壳属(Podosphaera),例如白叉丝单囊壳(Podosphaera leucotricha);单丝壳属(Sphaerotheca),例如苍耳单丝壳(Sphaerothecafuliginea);钩丝壳属(Uncinula),例如葡萄钩丝壳(Uncinula necator);
由锈病病原体引起的病害,例如,胶锈菌属(Gymnosporangium),例如褐色胶锈菌(Gymnosporangium sabinae);驼孢锈属(Hemileia),例如咖啡驼孢锈菌(Hemileiavastatrix);层锈菌属(Phakopsora),例如豆薯层锈菌(Phakopsora pachyrhizi)或山马蝗层锈菌(Phakopsorameibomiae);柄锈菌属(Puccinia),例如隐匿柄锈菌(Pucciniarecondite)、禾柄锈菌(Puccinia graminis)或条形柄锈菌(Puccinia striiformis);单胞锈菌属(Uromyces),例如疣顶单胞锈菌(Uromyces appendiculatus);
由卵菌纲(Oomycete)病原体引起的病害,例如,白锈菌属(Albugo),例如白锈菌(Albugo candida);盘霜霉属(Bremia),例如莴苣盘霜霉(Bremia lactucae);霜霉属(Peronospora),例如豌豆霜霉(Peronospora pisi)或寄生霜霉(P.brassicae);疫霉属(Phytophthora),例如致病疫霉(Phytophthora infestans);单轴霉属(Plasmopara),例如葡萄生单轴霉(Plasmopara viticola);假霜霉属(Pseudoperonospora),例如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonospora cubensis);腐霉属(Pythium),例如终极腐霉(Pythium ultimum);
由下述病原体引起的叶疱病(Leaf blotch)和叶枯病(leaf wilt):例如,链格孢属(Alternaria),例如茄链格孢(Alternaria solani);尾孢属(Cercospora),例如甜菜生尾孢(Cercospora beticola);枝孢属(Cladiosporium),例如黄瓜枝孢(Cladiosporiumcucumerinum);旋孢腔菌属(Cochliobolus),例如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:德氏霉属(Drechslera),同义:长蠕孢属(Helminthosporium))或宫部旋孢腔菌(Cochliobolus miyabeanus);刺盘孢属(Colletotrichum),例如豆刺盘孢(Colletotrichum lindemuthanium);锈斑病菌属(Cycloconium),例如油橄榄孔雀斑菌(Cycloconium oleaginum);间座壳属(Diaporthe),例如柑桔间座壳(Diaporthe citri);痂囊腔菌属(Elsinoe),例如柑桔痂囊腔菌(Elsinoe fawcettii);盘长孢属(Gloeosporium),例如悦色盘长孢(Gloeosporium laeticolor);小丛壳属(Glomerella),例如围小丛壳(Glomerella cingulata);球座菌属(Guignardia),例如葡萄球座菌(Guignardia bidwelli);小球腔菌属(Leptosphaeria),例如斑污小球腔菌(Leptosphaeria maculans);大毁壳属(Magnaporthe),例如灰色大毁壳(Magnaporthegrisea);微座孢属(Microdochium),例如雪霉微座孢(Microdochium nivale);球腔菌属(Mycosphaerella),例如禾生球腔菌(Mycosphaerella graminicola)、落花生球腔菌(M.arachidicola)和香蕉黑条叶斑病菌(M.fijiensis);暗球腔菌属(Phaeosphaeria),例如小麦颖枯病菌(Phaeosphaeria nodorum);核腔菌属(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或偃麦草核腔菌(Pyrenophora triticirepentis);柱隔孢属(Ramularia),例如生柱隔孢菌(Ramularia collo-cygni)或白斑柱隔孢(Ramulariaareola);喙孢属(Rhynchosporium),例如黑麦喙孢(Rhynchosporium secalis);壳针孢属(Septoria),例如芹菜小壳针孢(Septoria apii)或番茄壳针孢(Septoria lycopersii);壳多孢属(Stagonospora),例如颖枯壳多孢(Stagonospora nodorum);核瑚菌属(Typhula),例如肉孢核瑚菌(Typhula incarnata);黑星菌属(Venturia),例如苹果黑星病菌(Venturia inaequalis);
由下述病原体引起的根病和茎病:例如,伏革菌(Corticium),例如禾伏革菌(Corticium graminearum);镰孢属(Fusarium),例如尖镰孢(Fusarium oxysporum);顶囊壳属(Gaeumannomyces),例如禾顶囊壳(Gaeumannomyces graminis);根肿菌属(Plasmodiophora),例如云薹根肿菌(Plasmodiophora brassicae);丝核菌属(Rhizoctonia),例如立枯丝核菌(Rhizoctonia solani);帚枝杆孢属(Sarocladium),例如稻帚枝杆孢(Sarocladium oryzae);小核菌属(Sclerotium),例如小球菌核菌(Sclerotiumoryzae);塔普斯属(Tapesia),例如塔普斯梭状芽胞杆菌(Tapesia acuformis);根串珠霉属(Thielaviopsis),例如根串珠霉(Thielaviopsis basicola);
由下述病原体引起的穗和圆锥花序病(包括玉米穗轴):例如,链格孢属(Alternaria),例如链格孢属(Alternaria spp.);曲霉属(Aspergillus),例如黄曲霉(Aspergillus flavus);枝孢属(Cladosporium),例如枝状枝孢(Cladosporiumcladosporioides);麦角菌属(Claviceps),例如麦角菌(Claviceps purpurea);镰孢属(Fusarium),例如黄色镰孢(Fusariumculmorum);赤霉属(Gibberella),例如玉蜀黍赤霉(Gibberella zeae);小画线壳属(Monographella),例如雪腐小画线壳(Monographellanivalis);壳针孢属(Septoria),例如颖枯壳针孢(Septoria nodorum)。
由黑粉菌引起的病害,例如,轴黑粉菌属(Sphacelotheca),例如丝轴黑粉菌(Sphacelotheca reiliana);腥黑粉菌属(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries)或小麦矮腥黑粉菌(Tilletia controversa);条黑粉菌属(Urocystis),例如隐条黑粉菌(Urocystis occulta);黑粉菌属(Ustilago),例如裸黑粉菌(Ustilago nuda);
由下列病原体导致的果实腐烂:例如,曲霉属(Aspergillus),例如黄曲霉(Aspergillus flavus);葡萄孢属(Botrytis),例如灰葡萄孢(Botrytiscinerea);青霉属(Penicillium),例如扩展青霉(Penicillium expansum)或产紫青霉(Penicilliumpurpurogenum);根霉菌属(Rhizopus),例如葡枝根霉(Rhizopus stolonifer);核盘菌属(Sclerotinia),例如核盘菌(Sclerotinia sclerotiorum);轮枝孢属(Verticilium),例如黑白轮枝孢(Verticilium alboatrum);
由下述病原体引起的种子和土壤传播的腐烂和枯萎病以及幼苗的病害:例如,链格孢属(Alternaria),例如芸薹生链格孢(Alternaria brassicicola);丝囊霉属(Aphanomyces),例如根腐丝囊霉(Aphanomyces euteiches);壳二孢属(Ascochyta),例如兵豆壳二孢(Ascochyta lentis);曲霉属(Aspergillus),例如黄曲霉(Aspergillusflavus);枝孢属(Cladosporium),例如多主枝孢(Cladosporium herbarum);旋孢腔菌属(Cochliobolus),例如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:德氏霉属,平脐蠕孢属(Bipolaris)同义:长蠕孢属);刺盘孢属(Colletotrichum),例如番茄刺盘孢(Colletotrichum coccodes);镰孢属(Fusarium),例如黄色镰孢(Fusarium culmorum);赤霉属(Gibberella),例如玉蜀黍赤霉(Gibberella zeae);壳球孢属(Macrophomina),例如菜豆生壳球孢(Macrophomina phaseolina);微座孢属(Microdochium),例如雪霉微座孢(Microdochium nivale);小画线壳属(Monographella),例如雪腐小画线壳(Monographella nivalis);青霉属(Penicillium),例如扩展青霉(Penicilliumexpansum);茎点霉属(Phoma),例如黑胫茎点霉(Phoma lingam);拟茎点霉属(Phomopsis),例如大豆拟茎点霉(Phomopsis sojae);疫霉属(Phytophthora),例如恶疫霉(Phytophthora cactorum);核腔菌属(Pyrenophora),例如麦类核腔菌(Pyrenophoragraminea);梨孢属(Pyricularia),例如稻梨孢(Pyricularia oryzae);腐霉属(Pythium),例如终极腐霉(Pythium ultimum);丝核菌属(Rhizoctonia),例如立枯丝核菌(Rhizoctonia solani);根霉菌属(Rhizopus),例如稻根霉菌(Rhizopus oryzae);小核菌属(Sclerotium),例如齐整小核菌(Sclerotiumrolfsii);壳针孢属(Septoria),例如颖枯壳针孢(Septoria nodorum);核瑚菌属(Typhula),例如肉孢核瑚菌(Typhula incarnata);轮枝孢菌属(Verticillium),例如大丽花轮枝孢(Verticillium dahliae);
由下述病原体引起的癌性病害、瘿瘤和扫帚病(witches’broom):例如,丛赤壳属(Nectria),例如仁果干癌丛赤壳菌(Nectria galligena);
由下述病原体引起的枯萎病:例如,链核盘菌属(Monilinia),例如核果链核盘菌(Monilinia laxa);
由下述病原体引起的叶、花和果实的畸形:例如,外担菌属(Exobasidium),例如坏损外担菌(Exobasidium vexans);外囊菌属(Taphrina),例如畸形外囊菌(Taphrinadeformans);
由下述病原体引起的木本植物衰退病:例如,例如由根霉格孢菌(Phaeomoniellachlamydospora)、Phaeoacremonium aleophilum和地中海孢孔菌(Fomitiporiamediterranea)引起的依科病(Esca);灵芝属(Ganoderma),例如狭长孢灵芝(Ganodermaboninense);
由下述病原体引起的花和种子的病害:例如,葡萄孢菌属(Botrytis),例如灰葡萄孢菌(Botrytis cinerea);
由下述病原体引起的植物块茎的病害:例如,丝核菌属(Rhizoctonia),例如立枯丝核菌(Rhizoctonia solani);长蠕孢菌属(Helminthosporium),例如茄病长蠕孢(Helminthosporium solani);
本发明的活性成分在植物中还具有非常良好的强化作用(fortifying action)。因此其适用于调动植物自身的防御来抵抗不想要的微生物的侵害。
在本发明的上下文中,植物强化(诱导抗性)物质应理解为意指那些能够刺激植物的防御系统的物质,使得当随后用不想要的微生物接种时,经过处理的植物显示出对这些微生物的高度抗性。
在这种情况下,不想要的微生物应理解为意指植物病原性真菌和细菌。因此在处理之后,本发明的物质可用于保护植物一定的时间来抵抗所提及的病原体的侵害。在用所述活性成分处理植物后,所提供的保护时间通常持续1至10天,优选1至7天。
所述活性成分在防治植物病害所需的浓度下被植物良好地耐受,这一事实使得能够处理植物的地上部分、植物繁殖茎和种子,以及土壤。
本发明的活性成分可特别成功地用于防治葡萄栽培和马铃薯、水果和蔬菜生长中的病害,例如抵抗白粉病真菌,卵菌纲,例如疫霉属(Phytophthora)、单轴霉属(Plasmopara)、假霜霉属(Pseudoperonospora)、腐霉属(Pythium)。
本发明的活性成分还适合用于提高采收产量。此外,它们具有低毒性和良好的植物耐受性。
如果合适,在特定浓度或施用率下,本发明的化合物也可用作除草剂、安全剂、生长调节剂或改进植物特性的试剂,或作为杀微生物剂,例如杀真菌剂、抗真菌剂(antimycotics)、杀细菌剂、杀病毒剂(包括抗类病毒的试剂)或作为抗MLO(类支原体)和RLO(类立克次氏体)的试剂。如果合适,它们还可用作杀虫剂。如果合适,它们还可用作合成其它活性成分的中间体或前体。
用活性成分或组合物对植物和植物部位进行的本发明的处理可直接进行或通过使用常规处理方法作用于其周围环境、生境或存贮空间来进行,所述常规处理方法为,例如通过浸渍、喷洒、喷雾、灌溉、蒸发、撒粉、雾化、撒播、发泡、涂抹、撒布(spreading-on)、浇水(浇灌)、滴灌,以及在繁殖材料的情况下,特别是在种子的情况下,还可作为用于干种子处理的粉末、用于种子处理的溶液、用于浆液处理的水溶性粉末,通过结皮、包被一层或多层包衣等。还可通过超低容量法施用活性成分或者将活性成分制剂或活性成分本身注入到土壤中。
此外,在材料保护中,本发明的活性成分或组合物可用于保护工业材料来抵抗不想要的微生物(例如真菌)的侵害和破坏。
在本发明的上下文中,工业材料应理解为意指为了工业应用而制备的无生命材料。例如,可受本发明的活性成分保护而免于微生物蚀变或破坏的工业材料可以是粘合剂、胶料(sizes)、纸张和纸板、纺织品、皮革、木材、油漆和塑料制品、冷却润滑剂和其他可被微生物侵害或破坏的材料。受保护的材料的范围也包括生产设备部件,例如冷却水回路,其可能被微生物的增殖损害。在本发明范围内的工业材料优选包括粘合剂、胶料、纸张和卡片、皮革、木材、涂料、冷却润滑剂和传热流体,更优选木材。本发明的活性成分或组合物可以预防不利影响,例如腐烂、腐坏、变色、褪色或发霉。
本发明的用于防治不想要的真菌的方法还可用于保护贮存物。贮存物应理解为意指植物或动物来源的天然物质或其加工产品,其为天然来源的且需要长期保护。植物来源的贮存物,例如植物或植物部位(如茎、叶、块茎、种子、果实、谷粒)可在刚收获时或通过(预)干燥、润湿、粉碎、研磨、压制或烘培等加工后进行保护。贮存物还包括木材——不论是否是未加工的——例如建筑木材、电线杆和栅栏,或以成品形式,例如家具。动物来源的贮存物为,例如兽皮、皮革、毛皮或毛发。本发明的活性成分可以预防不利影响,如腐烂、腐坏、变色、褪色或发霉。
能够降解或改变工业材料的微生物包括,例如细菌、真菌、酵母、藻类和粘质生物体(slime organism)。本发明的活性成分优选抵抗真菌,尤其是霉菌、使木材变色和破坏木材的真菌(担子菌(Basidiomycetes)),以及抵抗粘质生物体和藻类。实例包括以下属的微生物:链格孢属(Alternaria),例如细链格孢(Alternaria tenuis);曲霉属(Aspergillus),例如黑曲霉(Aspergillus niger);毛壳属(Chaetomium),例如球毛壳菌(Chaetomium globosum);粉孢革菌属(Coniophora),例如粉孢革菌(Coniophorapuetana);香菇属(Lentinus),例如虎皮香菇(Lentinus tigrinus);青霉属(Penicillium),例如灰绿青霉(Penicillium glaucum);多孔菌属(Polyporus),例如变色多孔菌(Polyporus versicolor);金担霉属(Aureobasidium),例如出芽金担霉(Aureobasidium pullulans);核茎点霉属(Sclerophoma),例如核茎点霉(Sclerophomapityophila);木霉属(Trichoderma),例如绿色木霉(Trichoderma viride);埃希氏杆菌属(Escherichia),如大肠杆菌(Escherichia coli);假单胞菌属(Pseudomonas),例如铜绿假单胞菌(Pseudomonas aeruginosa);葡萄球菌属(Staphylococcus),例如金黄葡萄球菌(Staphylococcus aureus)。
本发明的杀真菌剂组合物可用于治疗性或保护性防治植物病原性真菌。因此,本发明还涉及用于防治植物病原性真菌的治疗性和保护性方法,所述方法通过使用本发明的活性成分或组合物——其被施用于种子、植物或植物部位、果实或植物生长的土壤——进行。
用于在作物保护中防治植物病原性真菌的本发明的组合物包含有效但无植物毒性量的本发明的有效成分。“有效但无植物毒性量”意指足以以令人满意的方式防治植物的真菌病害或完全根除真菌病害,并且同时不会引起任何明显的植物毒性症状的本发明组合物的量。一般而言,该施用率可在相对较宽的范围内变化。这取决于若干因素,例如待防治的真菌、植物、气候条件和本发明组合物的成分。
所有植物和植物部位均可根据本发明进行处理。在本文中,植物应理解为意指所有的植物及植物种群,如想要的和不想要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可以是通过常规育种法和优化方法或通过生物技术和基因工程法或这些方法的结合而获得,所述作物植物包括转基因植物并且包括可受或不受品种产权保护的植物品种。植物部位应理解为意指植物的地上和地下的所有部位和器官,如芽、叶、花和根,其实例包括叶、针叶、干、茎、花、子实体、果实、种子、根、块茎和根茎。植物部位还包括采收的材料和无性与有性繁殖材料,例如幼苗、块茎、根茎、插枝和种子。
可根据本发明进行处理的植物包括如下:棉花、亚麻、葡萄藤、水果、植物,例如蔷薇科(Rosaceae sp.)(例如仁果,如苹果和梨;以及核果,如杏、樱桃、扁桃和桃;和无核小果,如草莓)、茶藨子科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、壳斗科(Fagaceae sp.)、桑科(Moraceaesp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和大蕉)、茜草科(Rubiaceae sp.)(例如咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙子和葡萄柚);茄科(Solanaceae sp.)(例如番茄)、百合科(Liliaceae sp.)、菊科(Asteraceaesp.)(例如莴苣)、伞形科(Umbelliferae sp.)、十字花科(Cruciferae sp.)、藜科(Chenopodiaceae sp.)、葫芦科(Cucurbitaceae sp.)(例如黄瓜)、葱科(Alliaceae sp.)(例如韭葱和洋葱)、蝶形花科(Papilionaceae sp.)(例如豌豆);主要的作物植物例如禾本科(Gramineae sp.)(例如玉米、草坪、谷类如小麦、黑麦、稻、大麦、燕麦、粟和黑小麦)、菊科(Asteraceae sp.)(例如向日葵)、十字花科(Brassicaceae sp.)(例如白球甘蓝、红球甘蓝、西兰花、花椰菜、抱子甘蓝、小白菜、球茎甘蓝、小萝卜和油菜、芥菜、山葵和水芹)、豆科(Fabacae sp.)(例如豆类、花生)、蝶形花科(Papilionaceae sp.)(例如大豆)、茄科(Solanaceae sp.)(例如马铃薯)、藜科(Chenopodiaceae sp.)(例如甜菜、饲用甜菜、瑞士甜菜(Swiss chard)、甜菜根);园艺和森林中的有用植物和观赏植物;以及所述植物各自的转基因品种。
已发现包含下述成分的组合物不仅显示出预期的额外扩展的谱而且还具有协同作用:
(A)新晶形的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-咔唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯以及
(B)至少一种选自列表的杀真菌剂(参见下文)。
出人意料地是,该协同效应比在无定形的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-咔唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯与杀真菌剂结合的混合物的情况下的协同效应(WO2013/127704)更显著。
合适的混合组分(B)尤其为以下的杀真菌剂:
(1)麦角固醇生物合成抑制剂,例如(1.1)杀螟丹(aldimorph)、(1.2)氧环唑(azaconazole)、(1.3)联苯三唑醇(bitertanol)、(1.4)糠菌唑(bromuconazole)、(1.5)环丙唑醇(cyproconazole)、(1.6)苄氟三唑醇(diclobutrazole)、(1.7)苯醚甲环唑(difenoconazole)、(1.8)烯唑醇(diniconazole)、(1.9)烯唑醇-M(diniconazole-M)、(1.10)十二环吗啉(dodemorph)、(1.11)十二环吗啉乙酸盐(dodemorph acetate)、(1.12)氟环唑(epoxiconazole)、(1.13)乙环唑(etaconazole)、(1.14)氯苯嘧啶醇(fenarimol)、(1.15)腈苯唑(fenbuconazole)、(1.16)环酰菌胺(fenhexamid)、(1.17)苯锈啶(fenpropidin)、(1.18)丁苯吗啉(fenpropimorph)、(1.19)氟喹唑(fluquinconazole)、(1.20)呋嘧醇(flurprimidol)、(1.21)氟硅唑(flusilazole)、(1.22)粉唑醇(flutriafol)、(1.23)呋菌唑(furconazole)、(1.24)顺呋醚唑(furconazole-cis)、(1.25)己唑醇(hexaconazole)、(1.26)抑霉唑(imazalil)、(1.27)抑霉唑硫酸盐(imazalilsulfate)、(1.28)亚胺唑(imibenconazole)、(1.29)种菌唑(ipconazole)、(1.30)叶菌唑(metconazole)、(1.31)腈菌唑(myclobutanil)、(1.32)萘替芬(nafti fine)、(1.33)氟苯嘧啶醇(nuarimol)、(1.34)噁咪唑(oxpoconazole)、(1.35)多效唑(paclobutrazol)、(1.36)稻瘟酯(pefurazoate)、(1.37)戊菌唑(penconazole)、(1.38)粉病灵(piperalin)、(1.39)咪鲜胺(prochloraz)、(1.40)丙环唑(propiconazole)、(1.41)丙硫菌唑(prothioconazole)(1.42)稗草丹(pyributicarb)、(1.43)啶斑肟(pyrifenox)、(1.44)唑喹菌酮(quinconazole)、(1.45)硅氟唑(simeconazole)、(1.46)螺环菌胺(spiroxmine)、(1.47)戊唑醇(tebuconazole)、(1.48)特比萘芬(terbinafine)、(1.49)四氟醚唑(tetraconazole)、(1.50)三唑酮(triadimefon)、(1.51)三唑醇(triadimenol)、(1.52)十三吗啉(tridemorph)、(1.53)氟菌唑(triflumizole)、(1.54)嗪氨灵(triforine)、(1.55)灭菌唑(triticonazole)、(1.56)烯效唑(uniconazole)、(1.57)烯效唑-P(uniconazole-p)、(1.58)烯霜苄唑(viniconazole)、(1.59)伏立康唑(voriconazole)、(1.60)1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、(1.61)1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯、(1.62)N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基酰亚胺基甲酰胺、(1.63)N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}亚氨甲酰胺以及(1.64)O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]-1H-咪唑-1-硫代甲酸酯、(1.65)氯啶菌酯(Pyrisoxazole)。
(2)呼吸抑制剂(呼吸链抑制剂),例如(2.1)联苯吡菌胺(bixafen)、(2.2)啶酰菌胺(boscalid)、(2.3)萎锈灵(carboxin)、(2.4)氟嘧菌胺(diflumetorim)、(2.5)甲呋酰胺(fenfuram)、(2.6)氟吡菌酰胺(fluopyram)、(2.7)氟酰胺(flutolanil)、(2.8)氟唑菌酰胺(fluxapyroxad)、(2.9)呋吡菌胺(furametpyr)、(2.10)拌种胺(furmecyclox)、(2.11)吡唑萘菌胺(isopyrazam)(顺式差向异构外消旋体1RS,4SR,9RS与反式差向异构外消旋体1RS,4SR,9SR的混合物)、(2.12)吡唑萘菌胺(反式差向异构外消旋体)、(2.13)吡唑萘菌胺(反式差向异构对映异构体1R,4S,9S)、(2.14)吡唑萘菌胺(反式差向异构对映异构体1S,4R,9R)、(2.15)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.16)吡唑萘菌胺(顺式差向异构对映异构体1R,4S,9R)、(2.17)吡唑萘菌胺(顺式差向异构对映异构体1S,4R,9S)、(2.18)灭锈胺(mepronil)、(2.19)氧化萎锈灵(oxycarboxin)、(2.20)戊苯吡菌胺(penflufen)、(2.21)吡噻菌胺(penthiopyrad)、(2.22)氟唑环菌胺(sedaxane)、(2.23)噻氟菌胺(thifluzamide)、(2.24)1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(2.25)3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、(2.26)3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、(2.27)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.28)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.29)苯并烯氟菌唑(benzovindiflupyr)、(2.30)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-甲醇萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺和(2.31)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.32)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.33)1,3,5-三甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.34)1-甲基-3-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.35)1-甲基-3-(三氟甲基)-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.36)1-甲基-3-(三氟甲基)-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.37)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.38)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.39)1,3,5-三甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.40)1,3,5-三甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.41)麦锈灵(benodanil)、(2.42)2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、(2.43)isofetamid
(3)作用于呼吸链的复合物III的呼吸抑制剂(呼吸链抑制剂),例如(3.1)唑嘧菌胺(ametoctradin)、(3.2)吲唑磺菌胺(amisulbrom)、(3.3)嘧菌酯(azoxystrobin)、(3.4)氰霜唑(cyazofamid)、(3.5)甲香菌酯(coumethoxystrobin)、(3.6)丁香菌酯(coumoxystrobin)、(3.7)醚菌胺(dimoxystrobin)、(3.8)烯肟菌酯(enoxastrobin)、(3.9)噁唑菌酮(famoxadone)、(3.10)咪唑菌酮(fenamidone)、(3.11)菌螨酯(fenoxystrobin)、(3.12)氟嘧菌酯(fluoxastrobin)、(3.13)醚菌酯(kresoxim-methyl)、(3.14)苯氧菌胺(metominostrobin)、(3.15)肟醚菌胺(orysastrobin)、(3.16)啶氧菌酯(picoxystrobin)、(3.17)唑菌胺酯(pyraclostrobin)、(3.18)唑胺菌酯(pyrametostrobin)、(3.19)唑菌酯(pyraoxystrobin)、(3.20)吡菌苯威(pyribencarb)、(3.21)氯啶菌酯(triclopyricarb)、(3.22)肟菌酯(trifloxystrobin)、(3.23)(2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.24)(2E)-2-(甲氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺、(3.25)(2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺、(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基)丁-3-烯-2-亚基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.28)2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、(3.29)5-甲氧基-2-甲基-4-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)-2,4-二氢-3H-1,2,4-三唑-3-酮、(3.30)(2E)-2-{2-[({环丙基[(4-甲氧基苯基)亚氨基]甲基}硫烷基)甲基]苯基}-3-甲氧基丙-2-烯酸甲酯、(3.31)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰胺基-2-羟基苯甲酰胺、(3.32)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺,
(4)有丝分裂和细胞分裂抑制剂,例如(4.1)苯菌灵(benomyl)、(4.2)多菌灵(carbendazim)、(4.3)氯苯咪唑(chlorfenazole)、(4.4)乙霉威(diethofencarb)、(4.5)噻唑菌胺(ethaboxam)、(4.6)氟吡菌胺(fluopicolide)、(4.7)麦穗宁(fuberidazole)、(4.8)戊菌隆(pencycuron)、(4.9)噻菌灵(thiabendazole)、(4.10)甲基硫菌灵(thiophanate-methyl)、(4.11)硫菌灵(thiophanate)、(4.12)苯酰菌胺(zoxamide)、(4.13)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、(4.14)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪。
(5)具有多位点活性的化合物,例如(5.1)波尔多液(bordeaux mixture)、(5.2)敌菌丹(captafol)、(5.3)克菌丹(captan)、(5.4)百菌清(chlorothalonil)、(5.5)铜制剂例如氢氧化铜、(5.6)环烷酸铜(copper naphthenate)、(5.7)氧化铜(copper oxide)、(5.8)氧氯化铜(copper oxychloride)、(5.9)硫酸铜(copper sulphate)、(5.10)苯氟磺胺(dichlofluanid)、(5.11)二氰蒽醌(dithianon)、(5.12)多果定(dodine)、(5.13)多果定游离碱(dodine free base)、(5.14)福美铁(ferbam)、(5.15)氟灭菌丹(fluorofolpet)、(5.16)灭菌丹(folpet)、(5.17)双胍辛盐(guazatine)、(5.18)双胍辛乙酸盐(guazatineacetate)、(5.19)双胍辛胺(iminoctadine)、(5.20)双胍辛胺苯磺酸盐(iminoctadinealbesilate)、(5.21)双胍辛胺三乙酸盐(iminoctadine triacetate)、(5.22)代森锰铜(mancopper)、(5.23)代森锰锌(mancozeb)、(5.24)代森锰(maneb)、(5.25)代森联(metiram)、(5.26)代森联锌(metiram zinc)、(5.27)喹啉铜(oxine-copper)、(5.28)丙烷脒(propamidine)、(5.29)丙森锌(propineb)、(5.30)硫和硫制剂例如多硫化钙、(5.31)福美双(thiram)、(5.32)甲苯氟磺胺(tolylfluanid)、(5.33)代森锌(zineb)、(5.34)福美锌(ziram)、(5.35)敌菌灵(anilazine)。
(6)抗性诱导剂,例如(6.1)阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、(6.2)异噻菌胺(isotianil)、(6.3)烯丙苯噻唑(probenazole)、(6.4)噻酰菌胺(tiadinil)和(6.5)昆布多糖(laminarin)。
(7)氨基酸和蛋白质生物合成抑制剂,例如(7.1)、(7.2)灭瘟素-S(blasticidin-S)、(7.3)嘧菌环胺(cyprodinil)、(7.4)春雷霉素(kasugamycin)、(7.5)盐酸春雷霉素水合物(kasugamycin hydrochloride hydrate)、(7.6)嘧菌胺(mepanipyrim)、(7.7)嘧霉胺(pyrimethanil)、(7.8)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉、(7.9)土霉素(oxytetracycline)和(7.10)链霉素(streptomycin)。
(8)ATP生成抑制剂,例如(8.1)三苯基乙酸锡(fentin acetate)、(8.2)三苯基氯化锡(fentin chloride)、(8.3)毒菌锡(fentin hydroxide)、(8.4)硅噻菌胺(silthiofam)。
(9)细胞壁合成抑制剂,例如(9.1)苯噻菌胺(benthiavalicarb)、(9.2)烯酰吗啉(dimethomorph)、(9.3)氟吗啉(flumorph)、(9.4)异丙菌胺(iprovalicarb)、(9.5)双炔酰菌胺(mandipropamid)、(9.6)多抗霉素(polyoxins)、(9.7)多氧霉素(polyoxorim)、(9.8)有效霉素A(validamycin A)、(9.9)缬菌胺(valifenalate)、(9.10)多抗霉素B(polyoxinB)。
(10)脂和膜合成抑制剂,例如(10.1)联苯、(10.2)地茂散(chloroneb)、(10.3)氯硝胺(dicloran)、(10.4)敌瘟磷(edifenphos)、(10.5)土菌灵(etridiazole)、(10.6)3-碘代-2-丙炔基丁基氨基甲酸酯(iodocarb)、(10.7)异稻瘟净(iprobenfos)、(10.8)稻瘟灵(isoprothiolane)、(10.9)霜霉威(propamocarb)、(10.10)霜霉威盐酸盐(propamocarbhydrochloride)、(10.11)硫菌威(prothiocarb)、(10.12)吡菌磷(pyrazophos)、(10.13)五氯硝基苯(quintozene)、(10.14)四氯硝基苯(tecnazene)和(10.15)甲基立枯磷(tolclofos-methyl)。
(11)黑色素生物合成抑制剂,例如(11.1)环丙酰菌胺(capropamid)、(11.2)双氯氰菌胺(diclocymet)、(11.3)氰菌胺(fenoxanil)、(11.4)四氯苯酞(fthalid)、(11.5)咯喹酮(pyroquilon)、(11.6)三环唑(tricyclazole)和(11.7)2,2,2-三氟乙基{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁烷-2-基}氨基甲酸酯。
(12)核酸合成抑制剂,例如(12.1)苯霜灵(benalaxyl)、(12.2)高效苯霜灵(benalaxyl-M)(kiralaxyl)、(12.3)乙嘧酚磺酸酯(bupirimate)、(12.4)clozylacon、(12.5)二甲嘧酚(dimethirimol)、(12.6)乙嘧酚(ethirimol)、(12.7)呋霜灵(furalaxyl)、(12.8)噁霉灵(hymexazole)、(12.9)甲霜灵(metalaxyl)、(12.10)高效甲霜灵(metalaxyl-M)(mefenoxam)、(12.11)呋酰胺(ofurace)、(12.12)噁霜灵(oxadixyl)、(12.13)喹菌酮(oxolinic acid)和(12.14)辛噻酮(octhilinone)。
(13)信号转导抑制剂,例如(13.1)乙菌利(chlozolinate)、(13.2)拌种咯(fenpiclonil)、(13.3)咯菌腈(fludioxonil)、(13.4)异菌脲(iprodione)、(13.5)腐霉利(procymidone)、(13.6)苯氧喹啉(quinoxyfen)、(13.7)乙烯菌核利(vinclozolin)和(13.8)丙氧喹啉(proquinazid)。
(14)解偶联剂,例如(14.1)乐杀螨(binapacryl)、(14.2)敌螨普(dinocap)、(14.3)嘧菌腙(ferimzone)、(14.4)氟啶胺(fluazinam)和(14.5)消螨多(meptyldinocap)。
(15)其他化合物,例如(15.1)苯噻硫氰(benthiazole)、(15.2)3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噻嗪-4-氧化物(bethoxazin)、(15.3)卡巴西霉素(capsimycin)、(15.4)香芹酮(carvone)、(15.5)灭螨猛(chinomethionat)、(15.6)甲氧苯唳菌(pyriofenone)(chlazafenone)、(15.7)硫杂灵(cufraneb)、(15.8)环氟菌胺(cyflufenamid)、(15.9)霜脲氰(cymoxanil)、(15.10)啶酰菌胺(cyprosulphamide)、(15.11)棉隆(dazomet)、(15.12)咪菌威(debacarb)、(15.13)二氯芬(dichlorophen)、(15.14)哒菌清(diclomezine)、(15.15)野燕枯(difenzoquat)、(15.16)野燕枯甲基硫酸盐(difenzoquat methylsulphate)、(15.17)二苯胺(diphenylamine)、(15.18)eEcoMate、(15.19)胺苯吡菌酮(fenpyrazamine)、(15.20)氟酰菌胺(flumetover)、(15.21)唑呋草(fluoroimid)、(15.22)磺菌胺(flusulpHamide)、(15.23)flutianil、(15.24)三乙膦酸铝(fosetyl-aluminium)、(15.25)三乙膦酸钙(fosetyl-calcium)、(15.26)三乙膦酸钠((fosetyl-sodium)、(15.27)六氯苯(hexachlorobenzene)、(15.28)人间霉素(irumamycin)、(15.29)磺菌威(methasulphocarb)、(15.30)异硫氰酸甲酯(methylisothiocyanate)、(15.31)苯菌酮(metrafenone)、(15.32)灭粉霉素(mildiomycin)、(15.33)纳他霉素(natamycin)、(15.34)二甲基二硫代氨基甲酸镍(nickeldimethyldithiocarbamate)、(15.35)酞菌酯(nitrothal-isopropyl)、(15.37)oxamocarb、(15.38)oxyfenthiin、(15.39)五氯苯酚(pentachlorophenol)及其盐、(15.40)苯氧司林(phenothrin)、(15.41)亚磷酸(phosphoric acid)及其盐、(15.42)霜霉威乙膦酸盐(propamocarb-fosetylate)、(15.43)普罗帕诺欣钠(propanosine-sodium)、(15.44)吡吗啉(pyrimorph)、(15.45)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(15.46)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(15.47)硝吡咯菌素(pyrrolnitrine)、(15.48)特弗喹啉(tebufloquin)、(15.49)叶枯酞(tecloftalam)、(15.50)甲磺菌胺(tolnifanide)、(15.51)咪唑嗪(triazoxide)、(15.52)水杨菌胺(trichlamide)、(15.53)氰菌胺(zarilamid)、(15.54)(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬-7-基2-甲基丙酸酯、(15.55)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.56)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.57)1-(4-{4-[5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.58)1-(4-甲氧基苯氧基)-3,3-二甲基丁烷-2-基1H-咪唑-1-甲酸酯、(15.59)2,3,5,6-四氯-4-(甲磺酰基)吡啶、(15.60)2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮、(15.61)2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.62)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5R)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、(15.63)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5S)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、(15.64)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-{4-[4-(5-苯基-4,5-二氢-1,2-噁唑-3-基)-1,3-噻唑-2-基]哌啶-1-基}乙酮、(15.65)2-丁氧基-6-碘-3-丙基-4H-苯并吡喃-4-酮、(15.66)2-氯-5-[2-氯-1-(2,6-二氟-4-甲氧基苯基)-4-甲基-1H-咪唑-5-基]吡啶、(15.67)2-苯基苯酚和盐、(15.68)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.69)3,4,5-三氯吡啶-2,6-二腈、(15.70)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(15.71)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(15.72)5-氨基-1,3,4-噻重氮-2-硫醇、(15.73)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、(15.74)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.75)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.76)5-甲基-6-辛基[1,2,4]三唑[1,5-a]嘧啶-7-胺、(15.77)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.78)N'-(4-{[3-(4-氯苄基)-1,2,4-噻二唑-5-基]氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亚胺基甲酰胺、(15.79)N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.80)N-[(4-氯苯基)(氰基)甲基]-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.81)N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯烟酰胺、(15.82)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、(15.83)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘代烟酰胺、(15.84)N-{(E)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.85)N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.86)N'-{4-[(3-叔丁基-4-氰基-1,2-噻唑-5-基)氧基]-2-氯-5-甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(15.87)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-(1,2,3,4-四氢萘-1-基)-1,3-噻唑-4-甲酰胺、(15.88)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1R)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、(15.89)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1S)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、(15.90){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸戊酯、(15.91)吩嗪-1-甲酸、(15.92)喹啉-8-醇、(15.93)喹啉-8-醇硫酸盐(2:1)、(15.94){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯、(15.95)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(15.96)N-(4'-氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(15.97)N-(2',4'-二氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(15.98)3-(二氟甲基)-1-甲基-N-[4'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(15.99)N-(2',5'-二氟联苯-2-基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(15.100)3-(二氟甲基)-1-甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、(15.101)5-氟-1,3-二甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、(15.102)2-氯-N-[4'-(丙-1-炔-1-基)联苯-2-基]烟酰胺、(15.103)3-(二氟甲基)-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.104)N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、(15.105)3-(二氟甲基)-N-(4'-乙炔基联苯-2-基)-1-甲基-1H-吡唑-4-甲酰胺、(15.106)N-(4'-乙炔基联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、(15.107)2-氯-N-(4'-乙炔基联苯-2-基)烟酰胺、(15.108)2-氯-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.109)4-(二氟甲基)-2-甲基-N-[4'-(三氟甲基)联苯-2-基]-1,3-噻唑-5-甲酰胺、(15.110)5-氟-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、(15.111)2-氯-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.112)3-(二氟甲基)-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.113)5-氟-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、(15.114)2-氯-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.115)(5-溴-2-甲氧基-4-甲基吡啶-3-基)(2,3,4-三甲氧基-6-甲基苯基)甲酮、(15.116)N-[2-(4-{[3-(4-氯苯基)丙-2-炔-1-基]氧基}-3-甲氧基苯基)乙基]-N2-(甲磺酰基)缬氨酰胺、(15.117)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.118)丁-3-炔-1-基{6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯、(15.119)4-氨基-5-氟嘧啶-2-醇(互变异构的形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.120)3,4,5-三羟基苯甲酸丙酯、(15.121)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(15.122)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(15.123)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(15.124)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.125)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.126)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.127)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.128)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(15.129)5-(烯丙基硫烷基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(15.130)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.131)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.132)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.133)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(15.134)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(15.135)5-(烯丙基硫烷基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(15.136)5-(烯丙基硫烷基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(15.137)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.138)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.139)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.140)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.141)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.142)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.143)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.144)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.145)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(15.146)2-(6-苄基吡啶-2-基)喹唑啉、(15.147)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.148)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.149)脱落酸、(15.150)3-(二氟甲基)-N-甲氧基-1-甲基-N-[1-(2,4,6-三氯苯基)丙烷-2-基]-1H-吡唑-4-甲酰胺、(15.151)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亚氨基甲酰胺、(15.152)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.153)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.154)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.155)N'-{5-溴-6-[(顺-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.156)N'-{5-溴-6-[(反-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.157)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.158)N-环丙基-N-(2-环丙基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.159)N-(2-叔丁基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.160)N-(5-氯-2-乙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.161)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.162)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.163)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.164)N-环丙基-N-(2-环丙基-5-氟苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.165)N-(2-环戊基-5-氟苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.166)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.167)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.168)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.169)N-环丙基-N-(2-环丙基-5-甲基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.170)N-(2-叔丁基-5-甲基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.171)N-[5-氯-2-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.172)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基]-1H-吡唑-4-甲酰胺、(15.173)N-[2-氯-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.174)N-[3-氯-2-氟-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.175)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.176)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-硫代甲酰胺、(15.177)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲酰胺、(15.178)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.179)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.180)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.181)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(15.182)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
如果它们能够以其官能团为基础,则在(1)至(15)类中所提到的所有混合配对物可任选地与合适的碱或酸形成盐。
所有植物和植物部位均可根据本发明进行处理。在本文中,植物应理解为意指所有的植物及植物种群,如想要的和不想要的野生植物或作物植物(包括天然存在的作物植物)。作物植物可以是通过常规育种法和优化方法或通过生物技术和基因工程的方法或这些方法的结合而获得,所述作物植物包括转基因植物并且包括可受或不受品种产权保护的植物品种。植物部位应理解为意指植物的所有地上和地下部位和器官,如芽、叶、花和根,实例包括叶、针叶、茎、干、花、子实体、果实和种子、以及根、块茎和根茎。植物部位还包括采收的材料和无性与有性繁殖材料,例如插枝、块茎、根茎、分蘖和种子。
用所述新结晶活性成分或包含所述新结晶活性成分的活性成分结合物对植物和植物部位进行的本发明的处理可直接进行或通过常规处理方法通过使所述化合物作用于其周围、环境或贮藏空间而进行:例如浸渍、喷洒、蒸发、雾化(fogging)、撒播、撒布(spreading-on)、注入,并且在繁殖材料的情况下,特别是在种子的情况下,还可通过涂布一层或多层包衣。
可提及以下植物作为可根据本发明进行处理的植物:棉花、亚麻、葡萄藤、水果、植物,例如蔷薇科(Rosaceae sp.)(例如仁果,如苹果和梨;以及核果,如杏、樱桃、扁桃和桃;和浆果,如草莓)、茶藨子科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、壳斗科(Fagaceae sp.)、桑科(Moraceaesp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和大蕉)、茜草科(Rubiaceae sp.)(例如咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙子和葡萄柚);茄科(Solanaceae sp.)(例如番茄)、百合科(Liliaceae sp.)、菊科(Asteraceaesp.)(例如莴苣)、伞形科(Umbelliferae sp.)、十字花科(Cruciferae sp.)、藜科(Chenopodiaceae sp.)、葫芦科(Cucurbitaceae sp.)(例如黄瓜)、葱科(Alliaceae sp.)(例如韭葱和洋葱)、蝶形花科(Papilionaceae sp.)(例如豌豆);主要的作物植物例如禾本科(Gramineae sp.)(例如玉米、草坪、谷类如小麦、黑麦、稻、大麦、燕麦、粟和黑小麦)、菊科(Asteraceae sp.)(例如向日葵)、十字花科(Brassicaceae sp.)(例如白球甘蓝、红球甘蓝、西兰花、花椰菜、抱子甘蓝、小白菜、球茎甘蓝、小萝卜和油菜、芥菜、山葵和水芹)、豆科(Fabacae sp.)(例如豆类、花生)、蝶形花科(Papilionaceae sp.)(例如大豆)、茄科(Solanaceae sp.)(例如马铃薯)、藜科(Chenopodiaceae sp.)(例如甜菜、饲用甜菜、瑞士甜菜(Swiss chard)、甜菜根);园艺和森林中的有用植物和观赏植物;以及所述植物各自的转基因品种。
用本发明的所述新结晶活性成分或活性成分结合物对植物和植物部位进行的本发明的处理可直接进行或通过常规处理方法通过使所述化合物作用于其环境、生境或贮藏空间而进行:例如浸渍、喷洒、蒸发、雾化、撒播、撒布,并且在繁殖材料的情况下,特别是在种子的情况下,还可通过涂布一层或多层包衣。
早在种子在下述期间被侵染时,大多数由有害物引起的作物植物的损害就会发生:在种子贮存期间或在将种子撒入土壤中之后,以及在植物发芽期间或紧接着在植物发芽后。这个阶段特别关键,因为生长植物的根和芽特别敏感,即使微小的损害也可能导致整株植物的死亡。因此,通过使用合适的组合物来保护种子和发芽植物特别引人关注。
因此,本发明还特别涉及一种通过使用本发明的组合物来处理种子以保护种子和发芽植物免受有害物侵害的方法。本发明还涉及本发明组合物用于处理种子以保护种子和所得的植物免受有害物侵害的用途。本发明还涉及经过本发明的组合物处理以抵抗有害物的种子。种子应理解为意指常规种子或转基因种子。
在转基因种子的情况下,源自该种子的植物能够表达针对有害物的蛋白质。这通常采用包含至少一种异源基因的植物种子的形式,所述异源基因支配着具有特别的杀虫特性的多肽的表达。在本文中,转基因种子中的异源基因可源自微生物,如芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单胞菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棍状杆菌属(Clavibacter)、球囊霉属(Glomus)或胶霉属(Gliocladium)。本发明特别适用于处理这样的转基因种子,其包含至少一种源自芽孢杆菌属(Bacillus sp.)的异源基因,并且其基因产物显示出对抗欧洲玉米螟和/或玉米根虫的效力。特别优选衍生自苏云金芽孢杆菌(Bacillus thuringiensis)的异源基因。
通过使用本发明的组合物处理此类种子,某些害虫仅仅通过例如杀虫蛋白质的表达就可防治,并且种子的额外损害可通过本发明的组合物来避免。
本发明的组合物适合于保护如上所提及的在农业、温室、森林或园艺中使用的任何植物品种的种子。特别地,其采用下述种子的形式:玉米、花生、加拿大油菜、油菜、罂粟、大豆、棉花、甜菜(例如糖用甜菜和饲料甜菜)、稻、粟、小麦、大麦、燕麦、黑麦、向日葵、烟草、马铃薯或蔬菜(例如蕃茄、甘蓝类)。本发明的组合物同样适用于处理如上述已提到的水果植物和植物的种子。对于玉米、大豆、棉花、小麦和加拿大油菜或油菜的种子的处理尤其重要。
在本发明的上下文中,本发明的组合物被单独或以合适的制剂施用于种子。所述种子优选在这样的状态下处理:种子在处理过程中足够稳定而避免损害。通常,对种子的处理可在采收和播种之间的任何时间点进行。通常使用的种子是已与植物分离的,并且脱离了穗轴、壳、茎、表皮、毛或果实的果肉。
当处理种子时,通常需要确保对施用于种子的本发明的组合物的量和/或其他添加剂的量的选择为使得种子的发芽不会受损,或所得植物不受损害。特别是在活性成分在特定施用率下可表现出植物毒性效应的情况下,必须确保这点。
本发明的组合物可以直接施用,即,不包含其他组分并且不经稀释。通常优选将所述组合物以合适的制剂形式施用于种子。用于种子处理的合适的制剂和方法为本领域技术人员已知的并且记载于例如以下文献中:US 4,272,417 A、US 4,245,432 A、US 4,808,430A、US 5,876,739 A、US 2003/0176428 A1、WO 2002/080675 A1、WO 2002/028186 A2。
可将2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的所述新晶形转化成常规的拌种制剂,例如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂或其他用于种子的包衣材料,以及ULV制剂。这些制剂可用已知方法通过将活性成分与常规添加剂(例如常规增充剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、粘合剂、赤霉素以及水)进行混合而制备。
可存在于可根据本发明使用的拌种制剂中的着色剂为常用于此目的的所有着色剂。可使用颜料(其微溶于水)或染料(其可溶于水)。实例包括已知的名为罗丹明B(Rhodamine B)、C.I.色素红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的合适的润湿剂为可促进润湿并通常用于农业化学活性成分制剂中的所有物质。优选使用烷基萘磺酸盐,如二异丙基或二异丁基萘磺酸盐。
可存在于可根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为常用于农业化学活性成分制剂中的所有非离子、阴离子和阳离子分散剂。优选使用非离子或阴离子分散剂,或者非离子或阴离子分散剂的混合物。合适的非离子分散剂特别包括环氧乙烷/环氧丙烷嵌段聚合物、烷基苯酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚,以及其磷酸化或硫酸化衍生物。合适的阴离子分散剂特别为木素磺酸盐、聚丙烯酸盐和芳基磺酸盐/甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为常用于活性农业化学化合物制剂中的所有泡沫抑制物质。优选使用硅酮消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为农业化学组合物中可用于此目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为农业化学组合物中可用于此目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土、以及细碎二氧化硅。
可存在于可根据本发明使用的拌种制剂中的粘合剂为可用于拌种产品的所有常规粘合剂。优选实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素。
可存在于可根据本发明使用的拌种制剂中的赤霉素优可选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。所述赤霉素是已知的(参见R.Wegler“Chemie derPflanzenschutz-und”[Chemistry of the CropProtection Compositions and Pesticides],第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可以直接使用或预先用水稀释后使用,以处理宽范围的不同种子,包括转基因植物的种子。在这种情况下,与由表达形成的物质之间的相互作用也会产生额外的协同效应。
对于用可根据本发明使用的拌种制剂或由其加水制得的制剂进行的种子处理,所有常规可用于拌种的混合装置都是有用的。具体而言,拌种采用的步骤包括将种子引入混合器中、加入特定所需量的拌种制剂(以其本身或预先用水稀释后),然后全部混合直到制剂均匀地分布在种子上。如果合适,之后进行干燥操作。
附图2的说明
附图2:2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的新晶形的X-射线粉末衍射图。
所述新的固体形式的制备
将3g无定形2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式A)(按照WO2012025557中所记载的进行制备)与40ml异丙醇混合,并且加热至82℃。随后,在该温度下将悬浮液搅拌10分钟。然后将悬浮液静置至冷却到20℃,在该温度下再搅拌16小时。抽滤出沉淀的晶体,然后在室温和大气压下干燥。得到2.7g结晶的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式B),熔点范围为153-154℃。
1H-NMR(D6-DMSO,298K,400MHz)与WO 2012/025557中所记载的无定形状态的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的1H-NMR相符合。
实施例
通过下面的实施例说明在防治植物病原性有害真菌方面,晶体形式相对于无定形形式的优越性:
实施例1
疫霉属(Phytophthora)测试(番茄)/保护
为制备合适的活性成分制剂,将制剂用水悬浮且稀释到所需浓度。在本实施例中,将已知的无定形变型的物质2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式A),以及本发明的晶形的物质2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式B)均用作50ga.i./升的SC制剂。
为测试保护效力,用活性成分制剂以所述的施用率喷洒幼体植物。在喷洒涂层初步干燥后,用致病疫霉(Phytophthora infestans)的水性孢子悬浮液对所述植物进行接种。然后将植物放置于约20℃和100%相对大气湿度的培育箱中。
在接种后3天进行评价。在本发明中0%表示相当于对照品的效力,而100%效力表示没有观察到侵染。
表A
疫霉属(Phytophthora)测试(番茄)/保护
实施例2
单轴霉属(Plasmopara)测试(葡萄)/保护
为制备合适的活性成分制剂,将制剂用水悬浮且稀释到所需浓度。在本实施例中,将已知的无定形变型的物质2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式A),以及本发明的晶形的物质2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯(形式B)均用作50ga.i./升的SC制剂。
为测试保护效力,用活性成分制剂以所述的施用率喷洒幼体植物。在喷洒涂层初步干燥后,用葡萄生单轴霉(Plasmopara viticola)的水性孢子悬浮液对所述植物进行接种,然后在约20℃和100%相对大气湿度的培育箱中保留1天。随后将所述植物于约21℃和约90%相对大气湿度的温室中放置4天。然后着使所述植物湿润并且在培育箱中放置1天。
在接种后6天进行评价。在本发明中0%表示相当于对照品的效力,而100%效力表示没有观察到侵染。
表B
单轴霉属(Plasmopara)测试(葡萄)/保护
Claims (10)
1.2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯的晶形,其特征在于其在25℃下的X-射线粉末衍射具有至少3个下列2Θ(2theta)值:
2.权利要求1的晶形,其特征在于其在25℃下的X-射线粉末衍射具有至少4个如权利要求1中所述的2Θ值。
3.组合物,其包含权利要求1或2的新的固体形式以及合适的助剂。
4.权利要求1或2的晶形或权利要求3的组合物用于制备用于在植物中和/或植物上或者在植物种子中和/或植物种子上防治植物病原性有害真菌的组合物的用途。
5.权利要求1或2的晶形或权利要求3的组合物用于处理种子的用途。
6.用于在植物中和/或植物上或者在植物种子中和/或植物种子上进行防治的方法,其特征在于将权利要求1或2的新的固体形式或权利要求3的组合物施用至植物病原性有害真菌和/或其生境和/或种子。
7.用于制备如权利要求1或2所限定的化合物的方法,其包括以下步骤:
(a)在至少50℃温度下,将无定形的2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯悬浮于溶剂或溶剂混合物中,以及
(b)缓慢冷却悬浮液。
8.权利要求8的方法,其中分步地进行缓慢冷却。
9.权利要求8或9的方法,其中所用的溶剂或溶剂混合物选自异丙醇、甲苯、甲基-THF、碳酸二乙酯、氯苯、乙酸正丁酯和乙酸异丁酯、正丁醇、乙醇、丙二酸乙酯、甲基叔丁基醚,以及甲苯和丁醇的混合物、甲苯和乙酸正丁酯的混合物、丙二酸乙酯和甲基叔丁基醚的混合物、以及乙酸丁酯和甲基叔丁基醚的混合物。
10.权利要求8或9的方法,其中所用溶剂为异丙醇。
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