CN115484820A - 嗜球果伞素类型化合物防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂I的耐受性的氨基酸替代F129L的植物病原性真菌的用途 - Google Patents
嗜球果伞素类型化合物防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂I的耐受性的氨基酸替代F129L的植物病原性真菌的用途 Download PDFInfo
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- CN115484820A CN115484820A CN202180032882.8A CN202180032882A CN115484820A CN 115484820 A CN115484820 A CN 115484820A CN 202180032882 A CN202180032882 A CN 202180032882A CN 115484820 A CN115484820 A CN 115484820A
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
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- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
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- A—HUMAN NECESSITIES
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- 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
- A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
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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
- A01N43/72—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
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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
- A01N43/72—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
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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
- A01N43/72—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
- A01N43/82—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 three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/52—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by halogen atoms or by nitro or nitroso groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/54—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及式I的嗜球果伞素类型化合物及其N‑氧化物和盐防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L(也称为线粒体细胞色素b基因中的F129L突变)的植物病原性真菌的用途以及防除该类真菌的方法。本发明还涉及新的化合物,制备这些化合物的方法,包含至少一种该化合物的组合物以及涂有至少一种该化合物的种子。
Description
本发明涉及式I的嗜球果伞素类型化合物及其N-氧化物和盐防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂(QoI)的耐受性的氨基酸替代F129L(也称为线粒体细胞色素b基因中的F129L突变)的植物病原性真菌的用途以及防除该类真菌的方法。本发明还涉及新的化合物,制备这些化合物的方法,包含至少一种该化合物的组合物,植物健康应用以及涂有至少一种该化合物的种子。本发明还涉及一种防治在线粒体细胞色素b蛋白中具有氨基酸替代F129L的大豆锈病真菌(豆薯层锈菌(Phakopsora pachyrhizi))的方法。
本文所用“Qo抑制剂”包括能够通过与线粒体中细胞色素bc1复合物的泛氢醌氧化中心(ubihydroquinone oxidation center)结合而减弱和/或抑制呼吸的任何物质。该氧化中心通常位于线粒体内膜的外侧上。这些化合物中的许多也已知为嗜球果伞素类型或嗜球果伞素类似化合物。
在线粒体细胞色素b(CYTB)基因中的突变F129L应指编码“F”的密码子129(苯丙氨酸;例如TTT或TTC)的任何如下核苷酸替代,所述核苷酸替代导致产生编码“L”的密码子(亮氨酸;例如TTA,TTG,TTG,CTT,CTC,CTA或CTG),例如在CYTB(细胞色素b)基因中密码子129的第一个核苷酸由‘T’替代为‘C’(TTT替代为CTT),这在细胞色素b蛋白中在位置129产生由F到L的单氨基酸替代。已知该F129L突变赋予对Qo抑制剂的耐受性。
通常称为嗜球果伞素类型杀真菌剂的QoI杀真菌剂(Sauter 2007:第13.2.章嗜球果伞素类和其他配合物III抑制剂。W.;Schirmer,U.(编辑)-Modern CropProtection Compounds,第2卷,Wiley-VCH Verlag 457-495)常用于在作物中防治许多真菌病原体。Qo抑制剂通常通过在线粒体中与细胞色素bc1复合物(电子传递复合物III)的泛氢醌氧化中心结合以抑制呼吸而起作用。所述氧化中心位于线粒体内膜的外侧上。使用QoI的主要实例包括例如嗜球果伞素类在小麦上用于防治小麦壳针孢(Septoria tritici)(也已知为禾生球腔菌(Mycosphaerella graminicola)),后者为小麦叶枯病的起因。遗憾的是,该类QoI的广泛使用已经导致耐受该类QoI的突变病原体的选择(Gisi等,Pest ManagSci 56,833-841(2000))。已经在几种植物病原性真菌如小麦白粉菌(Blumeriagraminis)、斐济球腔菌(Mycosphaerella fijiensis)、古巴假霜霉(Pseudoperonsporacubensis)或苹果黑星病(Venturia inaequalis)中检测到对QoI的耐受性。在农业应用中对QoI的耐受性主要归因于在其细胞色素bc1复合物—已经发现被特定QoI控制的QoI目标蛋白—的细胞色素b基因中含有单氨基酸残基替代G143A的病原体(WO 2013/092224)。尽管几种商业QoI杀真菌剂也已经广泛用于大豆锈病防治,但未观察到在细胞色素b蛋白中赋予对QoI杀真菌剂的耐受性的单氨基酸残基替代G143A。
相反,大豆锈病在细胞色素b基因中获得不同基因突变,从而引起也赋予对QoI杀真菌剂的耐受性的单氨基酸替代F129L。常用QoI杀真菌剂,即唑菌胺酯(pyraclostrobin)、腈嘧菌酯(azoxystrobin)、啶氧菌酯(picoxystrobin)、肟醚菌胺(orysastrobin)、醚菌胺(dimoxystrobin)和叉氨苯酰胺(metominostrobin)对大豆锈病的效力已经降至对于农业实践具有实际问题的程度(例如Klosowski等(2016)Pest Manag Sci 72,1211-1215)。
尽管看起来肟菌酯(trifloxystrobin)不太受F129L氨基酸替代影响以达到与其他QoI杀真菌剂如腈嘧菌酯和唑菌胺酯相同的程度,但肟菌酯对于带有F129L QoI耐受性突变的真菌群体绝不像对于敏感群体一样有效(Crop Protection 27,(2008)427-435)。
WO 2017/157923公开了四唑化合物1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基苯基]-4-甲基四唑-5-酮防除含有所述F129L氨基酸替代的植物病原性真菌的用途。
因此,对于在作物中防治病原体诱发病害需要新的方法,所述作物包括遭受在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的F129L氨基酸替代的病原体影响的植物。此外,在许多情况下,尤其是在低施用率下,已知杀真菌的嗜球果伞素化合物的杀真菌活性并不令人满意,尤其是在高比例的真菌病原体在线粒体细胞色素b基因中含有赋予对Qo抑制剂的耐受性的突变的情况下。此外,持续需要更有效、毒性更低和/或环境更安全的新型杀真菌活性化合物。基于此,本发明的目的还是要提供对植物病原性真菌具有改进活性和/或更宽活性谱和/或对非目标生物体如脊椎动物和无脊椎动物具有甚至进一步降低的毒性的化合物。
根据本发明用于防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的F129L氨基酸替代的植物病原性真菌的嗜球果伞素类似化合物与肟菌酯的不同尤其在于含有在侧链的邻位连接于中心苯基环的特定基团—本文定义为R3。
因此,本发明涉及式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的用途:
其中
R1选自O和NH;
R2选自CH和N;
R3选自卤素、C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C6环烷基和-O-C1-C4烷基;
R4选自C1-C6烷基、C2-C4链烯基、C2-C4炔基、C1-C6卤代烷基、C2-C4卤代链烯基、C2-C4卤代炔基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)、-(C1-C2烷基)-O-(C1-C2卤代烷基)和-C1-C4烷基-C3-C6环烷基;
Ra选自卤素、CN、-NR5R6、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、-C(=O)-C1-C4烷基、-O-CH2-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,
并且其中Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的相同或不同基团Rb:
Rb选自卤素、CN、NH2、NO2、C1-C4烷基、C1-C4卤代烷基、-O-C1-C4烷基和-O-C1-C4卤代烷基;
R5、R6相互独立地选自H、C1-C6烷基、C1-C6卤代烷基和C2-C4炔基;n为选自0、1、2、3、4和5的整数。
细胞色素b(cytb,也称为cob)基因中的突变F129L应指编码“F”的密码子129(苯丙氨酸;例如TTT或TTC)的任何如下核苷酸替代,所述核苷酸替代导致产生编码“L”的密码子(亮氨酸;例如TTA,TTG,TTG,CTT,CTC,CTA或CTG),例如在细胞色素b基因中密码子129的第一个核苷酸由‘T’替代为‘C’(TTT替代为CTT),这在细胞色素b蛋白(Cytb)中在位置129产生由F(苯丙氨酸)到L(亮氨酸)的单氨基酸替代(F129L)。在本发明中,在细胞色素b基因中的突变F129L应理解为是在细胞色素b蛋白中在位置129由F(苯丙氨酸)到L(亮氨酸)的单氨基酸替代(F129L)。
许多其他植物病原性真菌,如锈病,尤其是大豆锈病(豆薯层锈菌和山马蟥层锈菌(Phakopsora meibromiae))以及来自链格孢属(Alternaria)、核腔菌属(Pyrenophora)和丝核菌属(Rhizoctonia)的真菌在细胞色素b基因中获得对Qo抑制剂赋予耐受性的F129L突变。
优选的真菌品种是早疫链格孢(Alternaria solani)、豆薯层锈菌、山马蟥层锈菌、大麦网斑内脐蠕孢(Pyrenophora teres)、小麦黄斑叶枯病菌(Pyrenophora tritici-repentis)和立枯丝核菌(Rhizoctonia solani);尤其是豆薯层锈菌。
本发明一方面涉及保护易受和/或受到在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌侵袭的植物的方法,该方法包括对所述植物施用至少一种式I化合物或者包含至少一种式I化合物的组合物,用至少一种式I化合物或者包含至少一种式I化合物的组合物处理所述植物的植物繁殖材料和/或对所述植物病原性真菌施用至少一种式I化合物或者包含至少一种式I化合物的组合物。
根据另一实施方案,该防除植物病原性真菌的方法包括:a)确定在线粒体细胞色素b蛋白中含有对Qo抑制剂赋予耐受性的氨基酸替代F129L的植物病原性真菌,或者处于因本文所定义的植物病原性真菌发生病害危险中的材料、植物、土壤或种子,以及b)用有效量的至少一种式I化合物或包含它的组合物处理所述真菌或材料、植物、土壤或植物繁殖材料。
术语“在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌”应理解为至少10%,优选至少30%,更优选至少50%,甚至更优选至少75%,最优选90-100%,尤其是95-100%的待防治真菌分离物在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的该F129L替代。
尽管就特定实施方案描述本发明,但该描述不应以限制性意义解释。
在详细描述本发明的示例性实施方案之前,给出对于理解本发明而言重要的定义。如本说明书和所附权利要求书中使用的那样,单数形式“一个”和“一种”也包括相应的复数,除非上下文另有明确规定。在本发明上下文中,术语“约”和“大约”表示本领域熟练技术人员理解为仍确保所述特征的技术效果的准确度区间。该术语通常表示与所示数值的偏差为±20%,优选±15%,更优选±10%,甚至更优选±5%。应理解的是术语“包含”并非限制性的。对本发明而言,术语“由……构成”被认为是术语“包括”的优选实施方案。
除非另有说明,阐述下列定义来说明和定义用来在本文描述本发明和所附权利要求书的各种术语的含义和范围。这些定义不应从字面意义上解释,因为它们并不意欲为一般定义并且仅与本申请相关。
术语“化合物I”涉及式I化合物。同样,该专门用语用于所有子式,例如“化合物I.2”涉及式I.2化合物或者“化合物V”涉及式V化合物等等。
术语“独立地”当在对变量的取代基选择上下文中使用时是指在不止一个取代基选自许多可能的取代基时,那些取代基可以相同或不同。
在各变量的上面定义中提到的有机结构部分或基团是各基团成员的单独列举的集合性术语。术语“Cv-Cw”显示在每种情况下可能的碳原子数。
术语“卤素”涉及氟、氯、溴和碘。
术语“C1-C4烷基”涉及具有1-4个碳原子的直链或支化饱和烃基,例如甲基(CH3)、乙基(C2H5)、丙基、1-甲基乙基(异丙基)、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基。
术语“C2-C4链烯基”涉及具有2-4个碳原子和在任意位置的双键的直链或支化不饱和烃基,如乙烯基、1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基。
术语“C2-C4炔基”涉及具有2-4个碳原子并且含有至少一个叁键的直链或支化不饱和烃基,如乙炔基、丙-1-炔基、丙-2-炔基、丁-1-炔基、丁-2-炔基、丁-3-炔基、1-甲基丙-2-炔基。
术语“C1-C4卤代烷基”涉及具有1-4个碳原子的直链或支化烷基,其中这些基团中的一些或所有氢原子可以被如上所述的卤原子替代,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、CH2-C2F5、CF2-C2F5、CF(CF3)2、1-氟甲基-2-氟乙基、1-氯甲基-2-氯乙基、1-溴甲基-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基。
术语“单卤代乙烯基”涉及其中一个氢原子被卤原子替代的乙烯基,例如1-氯乙烯基、1-溴乙烯基、1-氟乙烯基、2-氟乙烯基。同样,“二卤代乙烯基”涉及其中两个氢原子被卤原子替代的乙烯基。
术语“-O-C1-C4烷基”涉及经由氧在该烷基中的任意位置键合的具有1-4个碳原子的直链或支化烷基,例如OCH3、OCH2CH3、O(CH2)2CH3、1-甲基乙氧基、O(CH2)3CH3、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基。
术语“C3-C6环烷基”涉及具有3-6个碳环成员的单环饱和烃基,如环丙基(C3H5)、环丁基、环戊基或环己基。术语“C3-C6环烯基”涉及具有3-6个碳环成员和一个或多个双键的单环饱和烃基。
术语“3-6员杂环烷基”涉及除了碳原子外具有一个或多个杂原子如O、N、S作为环成员的3-6员单环饱和环体系。术语“C3-C6杂环烯基”涉及除了碳原子外具有一个或多个杂原子如O、N和S作为环成员并且具有一个或多个双键的3-6员单环体系。
术语“-C1-C4烷基-C3-C6环烷基”涉及具有1-4个碳原子的烷基(如上所定义),其中该烷基的一个氢原子被具有3-6个碳原子的环烷基替代。
术语“苯基”涉及C6H5。
术语含有1、2、3或4个选自O、N和S的杂原子的“5或6员杂芳基”应理解为是指具有5或6个环原子的芳族杂环。实例包括:
-除了碳原子外例如含有1、2或3个N原子和/或一个硫和/或一个氧原子的5员杂芳基:例如2-噻吩基、3-噻吩基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4-噻唑基、5-噻唑基、2-咪唑基、4-咪唑基和1,3,4-***-2-基;
-除了碳原子外例如含有1、2、3或4个N原子作为环成员的6员杂芳基,例如2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基和2-吡嗪基。
术语“C1-C2亚烷基连接基”是指一端键合于式I的核结构且另一端键合于该特定取代基的二价烷基如-CH2-或-CH2-CH2-。
本文所用“化合物”,尤其是“化合物I”包括所有立体异构和互变异构形式以及所有比例的其混合物,前药,同位素形式,其可农用盐、N-氧化物和S-氧化物。
术语“立体异构体”是用于单独化合物的所有异构体的通用术语,这些异构体的不同仅在于其原子在空间中的取向。术语立体异构体包括镜像异构体(对映体),镜像异构体混合物(外消旋体,外消旋混合物),几何(顺/反或E/Z)异构体以及具有不止一个手性中心的化合物的异构体—相互不为镜像(非对映体)。术语“互变异构体”涉及两种(或更多种)仅在一个(或多个)可移动原子的位置和电子分布上相互不同的化合物的共存,例如酮-烯醇互变异构体。本文所用术语“可农用盐”包括取决于在本文所述化合物上发现的特定取代基而用酸或碱制备的活性化合物的盐。“N-氧化物”涉及含氮杂芳基或杂环的氮原子的氧化物。N-氧化物可以在氧化剂,例如过氧化物如间氯过苯甲酸或过氧化氢存在下形成。N-氧化物涉及也已知为胺-N-氧化物的氧化胺并且为含有N→O键的化合物。
就各变量而言,中间体的实施方案对应于化合物I的实施方案。
优选那些化合物I和适用的话还有本文所提供的所有子式化合物,例如式I.1和I.2化合物,以及中间体如化合物II、III、IV和V,其中各取代基和变量(如n、R1、R2、R3、R4、R5、R6、Ra和Rb)相互独立地或者更优选组合(2个或更多个本文所定义的取代基的任何可能组合)具有下列含义:
还优选这样的用途、方法、混合物和组合物,其中各定义(如植物病原性真菌、处理、作物、化合物II、其他活性成分、溶剂、固体载体)相互独立地或者更优选组合具有下列含义,甚至更优选与本文中化合物I的优选含义组合(2个或更多个本文所提供的定义的任何可能组合):
本发明的一个实施方案涉及其中R1选自O和NH;并且R2选自CH和N,条件是在R1是NH的情况下R2是N的化合物I的上述用途和/或施用方法(本文统称为“用途”)。更优选R1是NH。尤其R1是NH且R2是N。另一实施方案涉及其中R1是O且R2是CH的化合物I的用途。
根据另一实施方案,R3选自卤素、C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C5环烷基和-O-C1-C4烷基;优选选自卤素、C1-C2烷基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C2烷基;更优选选自C1-C2烷基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C2烷基;甚至更优选选自卤素、C1-C2烷基、C2-C3链烯基、CHF2、CFH2、-O-C1-C2烷基和环丙基,甚至更优选选自C1-C2烷基、乙烯基、CHF2、CFH2、OCH3和环丙基;特别优选选自甲基、乙烯基、CHF2和CFH2;尤其是甲基。
根据一个实施方案,R4选自C1-C6烷基、C2-C4链烯基、-C(=O)-C1-C2烷基、C1-C6卤代烷基、C2-C4卤代链烯基、-(C1-C2烷基)-O-(C1-C2烷基)和-CH2-环丙基,更优选选自C1-C4烷基、C2-C4链烯基、-C(=O)-C1-C2烷基、C1-C4卤代烷基、C2-C4卤代链烯基、-(C1-C2烷基)-O-(C1-C2烷基)和-CH2-环丙基,甚至更优选选自C1-C4烷基和C1-C4卤代烷基,特别优选选自甲基和C1卤代烷基;尤其是甲基。
根据另一实施方案,n为1、2、3、4或5,更优选n为1、2或3,甚至更优选n为1或2;n尤其为1。
根据另一实施方案,n为0、1、2或3,更优选0、1或2,尤其是0。
根据另一实施方案,n为2并且两个取代基Ra优选在2,3位(意味着一个取代基在2位,另一个在3位);2,4位;2,5位;3,4位或3,5位,甚至更优选在2,3位或2,4位。
根据另一实施方案,n为3并且两个取代基Ra优选在2、3和4位。
根据另一实施方案,Ra选自CN、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、-O-CH2-(=N-O-C1-C4烷基)-C1-C4烷基、-C(=N-O-C1-C4烷基)-C(=O-NH-C1-C4烷基)、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-5员杂环烷基、3-5员杂环烯基和5或6员杂芳基,其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,并且其中Ra的脂族和环状结构部分未被取代或者带有1、2或3个相互独立地选自卤素、CN、NH2、NO2、C1-C2烷基和C1-C2卤代烷基的相同或不同基团Rb。
更优选Ra选自C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=N-O-C1-C2烷基)-C1-C2烷基、-O-CH2-C(=N-O-C1-C2烷基)-C1-C2烷基、C3-C4环烷基、-C1-C2烷基-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基、杂环烷基和杂芳基直接或者经由氧原子或经由亚甲基连接基键合,并且其中Ra的脂族或环状结构部分未被取代或者带有1、2或3个相互独立地选自卤素、CN、C1-C2烷基和C1-C2卤代烷基的相同或不同基团Rb。
甚至更优选Ra选自C1-C3烷基、C2-C3链烯基、C2-C3炔基、-O-C1-C3烷基、-C(=N-O-C1-C2烷基)-C1-C2烷基、C3-C4环烷基、-C1-C2烷基-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基和杂芳基直接或者经由亚甲基连接基键合,并且其中Ra的脂族和环状结构部分未被取代或者带有1、2或3个相互独立地选自卤素、CN、甲基和C1卤代烷基的相同或不同基团Rb。
特别优选Ra选自卤素、C1-C4烷基、C2-C3链烯基、C2-C3炔基、-O-C1-C4烷基、-C(=N-O-C1-C2烷基)-C1-C2烷基和苯基,其中Ra的脂族或环状结构部分未被取代或者带有1、2或3个相互独立地选自卤素、CN、甲基和C1卤代烷基的相同或不同基团Rb。
根据另一实施方案,R5、R6相互独立地优选选自H、C1-C4烷基、C1-C4卤代烷基和C2-C4炔基,更优选选自H和C1-C4烷基。
根据另一优选实施方案,本发明涉及式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的用途,其中:
R1选自O和NH;以及
R2选自CH和N,条件是在R1是NH的情况下R2是N;
R3选自卤素、C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C4烷基;
R4选自C1-C4烷基、C1-C4卤代烷基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)和-CH2-环丙基;
Ra选自卤素、CN、-NR5R6、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、-C(=O)-C1-C4烷基、-O-CH2-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,
并且其中Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的相同或不同基团Rb:
Rb选自卤素、CN、NH2、NO2、C1-C4烷基、C1-C4卤代烷基、-O-C1-C4烷基和-O-C1-C4卤代烷基;
R5、R6相互独立地选自H、C1-C6烷基和C2-C4炔基;
n为选自0、1、2和3的整数。
某些式I的嗜球果伞素类型化合物已经描述于EP 370629和WO 1998/23156中。然而,没有提到这些化合物抑制在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的F129L替代的真菌病原体。
本发明化合物与上述公布中所述那些的不同在于R3是脂族或环状取代基且Ra是未被卤代的取代基。
因此,根据第二方面,本发明提供了由式I表示的新型式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐:
其中
R1选自O和NH;
R2选自CH和N;
R3选自C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C6环烷基和-O-C1-C4烷基;
R4选自C1-C6烷基、C2-C4链烯基、C2-C4炔基、C1-C6卤代烷基、C2-C4卤代链烯基、C2-C4卤代炔基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)、-(C1-C2烷基)-O-(C1-C2卤代烷基)和-C1-C4烷基-C3-C6环烷基;
Ra选自CN、NH-C1-C4烷基、N(C1-C4烷基)2、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,
并且其中Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的相同或不同基团Rb:
Rb选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基;
n为选自0、1、2、3、4和5的整数。
本发明的一个实施方案涉及优选的化合物I,其中R1选自O和NH;并且R2选自CH和N,条件是在R1是NH的情况下R2是N。更优选R1是NH。尤其R1是NH且R2是N。另一实施方案涉及其中R1是O且R2是CH的化合物I。
根据另一实施方案,R3选自卤素、C1-C4烷基、C2-C3链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C6环烷基和-O-C1-C4烷基;优选选自卤素、C1-C2烷基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C2烷基;优选选自C1-C4烷基、C2-C3链烯基、单卤代甲基、二卤代甲基、C3-C4环烷基和-O-C1-C4烷基;进一步更优选选自C1-C2烷基、CHF2、CFH2、环丙基和OCH3;特别优选选自甲基、CHF2和CFH2;尤其R3是甲基。
根据另一实施方案,R4选自C1-C4烷基、C2-C4链烯基、-C(=O)-C1-C2烷基、C1-C4卤代烷基、C2-C4卤代链烯基、-(C1-C2烷基)-O-(C1-C2烷基)和-CH2-环丙基,更优选选自C1-C4烷基和C1-C4卤代烷基,甚至更优选选自甲基和C1卤代烷基;尤其是甲基。
根据另一实施方案,n为1、2、3、4或5,更优选n为1、2或3,甚至更优选n为1或2;n尤其为1。
根据另一实施方案,n为0、1、2或3,更优选0、1或2,尤其是0。
根据另一实施方案,n为2并且两个取代基Ra优选在2,3位(意味着一个取代基在2位,另一个在3位);2,4位;2,5位;3,4位或3,5位,甚至更优选在2,3位或2,4位。
根据另一实施方案,n为3并且两个取代基Ra优选在2、3和4位。
根据另一实施方案,Ra选自CN、NH-C1-C4烷基、N(C1-C4烷基)2、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C4烷基、-C=(N-O-C1-C2烷基)-C1-C2烷基、C3-C4环烷基、-O-C3-C4环烷基、苯基、3-5员杂环烷基、3-5员杂环烯基和5或6员杂芳基,其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合。
优选Ra选自CN、NH-C1-C2烷基、N(C1-C2烷基)2、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C2烷基、-C=(N-O-CH3)-CH3、C3-C4环烷基、-O-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基、杂环烷基和杂芳基直接或者经由氧原子或经由亚甲基连接基键合。
更优选Ra选自CN、C1-C3烷基、-O-C1-C3烷基、-C=(N-O-CH3)-CH3、C3-C4环烷基、-O-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基、杂环烷基和杂芳基直接或者经由氧原子或经由亚甲基连接基键合。
Ra尤其选自CN、C1-C2烷基、乙烯基、乙炔基、-O-C1-C2烷基和-C=(N-O-CH3)-CH3。
根据Ra的上述实施方案,上述杂环烷基更优选是4员杂环烷基,其中所述杂环烷基除了碳原子外含有1个选自N、O和S的杂原子,优选N。
根据Ra的上述实施方案,上述杂芳基更优选是5员杂芳基,其中所述杂芳基除了碳原子外含有1或2个选自N、O和S,优选N和O的杂原子。
根据Ra的上述实施方案,Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基的相同或不同基团Rb;更优选仅Ra的环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基的相同或不同基团Rb;甚至更优选仅Ra的苯基结构部分未被取代或者带有1、2、3、4或5个选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基的相同或不同基团Rb;所述苯基尤其未被取代或者带有1、2或3个选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基的相同或不同基团Rb。
根据另一优选实施方案,本发明涉及式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐,其中:
R1选自O和NH;以及
R2选自CH和N,条件是在R1是NH的情况下R2是N;
R3选自卤素、C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C4环烷基和-O-C1-C4烷基;
R4选自C1-C4烷基、C1-C4卤代烷基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)和-CH2-环丙基;
Ra选自C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、-O-CH2-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、-C1-C2烷基-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由C1-C2亚烷基连接基键合,
并且其中所述苯基未被取代或者带有1、2或3个相同或不同的基团Rb:
Rb选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基;
n为选自0、1、2和3的整数。
根据另一实施方案,R1是O且R2是N,这些化合物具有式I.1:
根据另一实施方案,R1是O且R2是CH,这些化合物具有式I.2:
根据另一实施方案,R1是NH且R2是N,这些化合物具有式I.3:
优选化合物I的R3是下列基团3-1至3-6中的一个:
甚至更优选R3是CH3、OCH3、CHF2或C3H5,尤其是CH3。
本发明的特别优选实施方案涉及其中R4是下列基团4-1至4-8之一的化合物I:
本发明的特别优选实施方案涉及其中Ra选自下列基团a-1至a-10之一的化合物I:
根据另一实施方案,n为1。更优选Ra在邻位(2-Ra),这些化合物具有式I.A:
其中甚至更优选R1是O且R2是N。根据另一实施方案,Ra在间位(3-Ra),这些化合物具有式I.B:
其中甚至更优选R1是O且R2是N。
根据另一实施方案,n为2。更优选n为2并且两个Ra取代基均在间位(3,5-Ra),这些化合物具有式I.C:
其中甚至更优选R2是N。根据另一实施方案,n为2并且两个Ra取代基均在邻位(2,6-Ra),这些化合物具有式I.D:
其中甚至更优选R2是N。根据另一实施方案,n为2并且两个Ra取代基在邻位和间位,这些化合物具有式I.E:
其中甚至更优选R2是N。根据另一实施方案,n为2并且两个Ra取代基在邻位和对位,这些化合物具有式I.F:
其中甚至更优选R2是N。
在一个实施方案中,化合物I具有式I.3并且n、Ra、R3和R4如下表A的任一行所定义,这些化合物称为I.3-A-1至I.3-A-217。
在另一实施方案中,化合物I具有式I.2并且n、Ra、R3和R4如下表A的任一行所定义,这些化合物称为I.2-A-1至I.2-A-217。
在一个实施方案中,化合物I具有式I.1并且n、Ra、R3和R4如下表A的任一行所定义,这些化合物称为I.1-A-1至I.1-A-217。
表A:
合成
这些化合物可以通过类似于已知的现有技术方法(例如EP 463488)的各种途径得到,有利的是通过在下列方案1-4以及本申请的试验部分所示的合成得到。
一种制备化合物I的合适方法示于方案1中。
方案1:
这开始于使用羟胺盐酸盐和碱如吡啶、氢氧化钠或乙酸钠在极性溶剂如甲醇、甲醇-水混合物或乙醇中在60-100℃,优选约65℃的反应温度下将酮转化为相应肟。在其中得到E/Z混合物的情况下,异构体可以通过本领域已知的提纯技术(例如柱层析、结晶、蒸馏等)分离。然后在碱性条件下使用例如氢化钠、碳酸铯或碳酸钾作为碱并且使用有机溶剂如二甲基甲酰胺(DMF)或乙腈,优选使用碳酸铯作为碱和乙腈作为溶剂在约24℃的室温(RT)下进行与中间体IV的偶联,其中X是离去基团如卤素、甲苯磺酸酯和甲磺酸酯,优选X是Cl或Br。其中R1是O的酯化合物I可以通过在RT下使用四氢呋喃(THF)作为溶剂与甲胺(优选40%水溶液)反应而转化为其中R1是NH的式I的酰胺。
制备化合物I的另一通用方法示于方案2中。
方案2:
使用碱如三乙胺在DMF中使中间体IV与N-羟基琥珀酰亚胺VI反应。反应温度通常为50-70℃,优选约70℃。向相应O-苄基羟胺—中间体VIII的转化通过除去邻苯二甲酰亚胺基团实现,这优选使用水合肼在甲醇作为溶剂中在25℃下进行。替换地,使用甲胺在甲醇作为溶剂中在25℃下除去邻苯二甲酰亚胺基团可以提供中间体IX。中间体VIII和中间体IX分别可以使用乙酸或吡啶在甲醇作为溶剂中在50-65℃的温度下与酮缩合。替换地,该缩合还可以用乙醇钛(IV)(Ti(OEt)4)使用THF作为溶剂在约70℃下进行。所需产物通常伴随有不希望的异构体,后者例如可以通过柱层析、结晶除去。
制备中间体IV的通用方法示于方案3中。
方案3:
化合物XI可以通过锂-卤素交换或者通过产生格利雅试剂并进一步与草酸二甲酯或草酸氯甲酯在溶剂存在下反应而由X得到。优选的溶剂是THF、2-甲基-THF并且温度可以为-70℃至-78℃。将中间体XI转化为中间体XII可以使用N-甲基羟胺盐酸盐和碱如吡啶或乙酸钠在极性溶剂如甲醇中实现。反应温度优选为约65℃。通常得到E/Z混合物,异构体可以通过本领域已知的提纯技术(例如柱层析、结晶)分离。中间体XII的溴化提供所需中间体化合物IV,其中R1是O并且R2=N。中间体XII与N-溴代琥珀酰亚胺在溶剂如四氯化碳、氯苯、乙腈中使用自由基引发剂如1,1'-偶氮二(环己烷甲腈)或偶氮二异丁腈的该反应在70-100℃的温度下进行。优选的自由基引发剂是1,1'-偶氮二(环己烷甲腈),优选的溶剂是氯苯且优选的温度为80℃。
含有不同取代基R3的化合物的合成按照与其中R3是溴的方案3类似的顺序进行。中间体III与其中R3是溴的中间体IV的偶联提供如上所述的化合物I。使用标准化学反应,如Suzuki或Stille反应,可以将溴基团转化为例如其他R3取代基如环烷基、烷氧基和链烯基。例如乙烯基的额外转化提供具有其他R3取代基如乙基、CN和卤代烷基的化合物I。
大多数通式II的酮可市购,然而对于不能市购的而言,这些的制备使用现有技术中已知的方法内部进行。方案4描述了合成这些酮的各种文献已知方法。
方案4:
酮II可以由相应的带卤素前体XIV得到,其中X优选是溴或碘。在化合物XIII中使用正丁基锂的锂-卤素交换(J Org Chem,1998,63(21),7399-7407)或者使用THF作为溶剂合成相应格利雅试剂(Nature Comm,2017,8(1),1-7)以及随后与N-甲氧基-N-甲基乙酰胺在约-70℃至-78℃下反应可以提供酮II。替换地,化合物XIV和三丁基(1-乙氧基乙烯基)锡烷在具有合适配体的过渡金属催化剂,优选钯存在下在溶剂如二烷中在约100℃的反应温度下的偶联反应,然后用1N HCl处理可以提供酮II(Org Lett,2016,18(7),1630-1633,WO 2018/115380)。XIV与1,4-丁二醇乙烯基醚在具有合适配体的过渡金属催化剂,优选钯以及溶剂如1,2-丙二醇和碱如碳酸钠存在下在约120℃的反应温度下反应,然后用1N HCl处理可以提供酮II(Chem A Eur J,2008,14(18),5555-5566)。另一方法使用酸化合物XV,可以将其转化为相应的Weinreb酰胺或羧酸酯XVII并随后与甲基溴化镁(MeMgBr)在溶剂如THF中于-78℃至0℃,优选0℃的温度下反应而提供酮II。另一方法使用腈XVI与MeMgBr的反应,这在溶剂如THF或甲苯,优选THF中进行并且反应温度为25-60℃,优选60℃,然后用1NHCl处理(Eur J Med Chem,2015,102,582-593)。
化合物I及其组合物分别适合作为对宽范围的植物病原性真菌有效的杀真菌剂,所述植物病原性真菌包括土传真菌,尤其来自根肿菌纲(Plasmodiophoromycetes)、Peronosporomycetes(同义词卵菌纲(Oomycetes))、壶菌纲(Chytridiomycetes)、接合菌纲(Zygomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)和半知菌纲(Deuteromycetes)(同义词不完全菌纲(Fungi imperfecti))的土传真菌。它们可以作为叶面杀真菌剂、拌种用杀真菌剂和土壤杀真菌剂用于作物保护中。
化合物I及其组合物优选可以用于在各种栽培植物如禾谷类,例如小麦、黑麦、大麦、小黑麦、燕麦或稻;甜菜,水果,豆科植物如大豆,油料植物,葫芦科植物,纤维植物,柑桔类水果,蔬菜,月桂类植物,能量和原料植物,玉米;烟草;坚果;咖啡;茶;香蕉;葡萄藤(食用葡萄和酿酒用葡萄);天然橡胶植物或观赏和森林植物;植物繁殖材料如种子以及这些植物的作物材料上防治植物病原性真菌。
根据本发明,所有上面的栽培植物应理解为包括所有属于相应栽培植物的属种、亚种、变种、品种和/或杂种,包括但不限于冬季和春季品种,尤其是禾谷类如小麦和大麦,以及油籽油菜,例如冬小麦、春小麦、冬大麦等等。
玉米也已知为印第安玉米或玉蜀黍(甜玉米(Zea mays)),其包括所有种类的玉米如饲料玉米和甜玉米。根据本发明包括所有玉米栽培品种或品种,尤其是不确定和确定的栽培品种或品种。
术语“栽培植物”应理解为包括已经通过诱变或基因工程修饰以对植物提供新性状或者修饰已经存在的性状的植物。
化合物I及其组合物分别特别适合防治植物病害的下列致病因子:大豆和禾谷类上的锈病(例如大豆上的豆薯层锈菌和山马蟥层锈菌(P.meibomiae);小麦上的小麦叶锈菌(Puccinia tritici)和小麦条锈菌(P.striiformis));特种作物、大豆、油籽油菜和向日葵上的霉病(例如草莓和葡萄藤上的灰葡萄孢(Botrytis cinerea),油籽油菜、向日葵和大豆上的核盘菌(Sclerotinia sclerotiorum)、小核盘菌(S.minor)和白绢病(S.rolfsii));禾谷类上的镰孢霉属(Fusarium)病害(例如小麦上的大刀镰孢(Fusarium culmorum)和禾本科镰孢(F.graminearum));特种作物上的霜霉病(例如葡萄藤上的葡萄生单轴霉(Plasmopara viticola),土豆上的致病疫霉(Phytophthora infestans));特种作物和禾谷类上的白粉病(例如葡萄藤上的葡萄钩丝壳(Uncinula necator),各种特种作物上的白粉菌属(Erysiphe),禾谷类上的小麦白粉菌);以及禾谷类、大豆和玉米上的叶斑病(例如禾谷类上的小麦壳针孢和颖枯壳多孢(S.nodorum),大豆上的大豆壳针孢(S.glycines),玉米和大豆上的尾孢属(Cercospora))。
化合物I及其组合物分别还适合在储存产品或收获产品的保护中以及在材料保护中防治有害微生物。
化合物I直接或以组合物形式通过用杀真菌有效量的活性物质处理真菌,需要防止真菌侵袭的植物、植物繁殖材料如种子、土壤、表面、材料或空间而使用。施用可以在植物、植物繁殖材料如种子、土壤、表面、材料或空间被真菌侵染之前和之后进行。
农业化学组合物包含杀真菌有效量的化合物I。术语“杀真菌有效量”表示足以在栽培植物上或在储存产品或收获产品或者材料保护中防治有害真菌且不对被处理植物、被处理储存产品或收获产品或者被处理材料引起显著损害的量的组合物或化合物I。该量可以在宽范围内变化且取决于各种因素如待防治的真菌品种、被处理的栽培植物、储存产品、收获产品或材料、气候条件以及所用具体化合物I。
植物繁殖材料可以在种植或移栽时或在种植或移栽之前用化合物I本身或包含至少一种化合物I的组合物预防性地处理。
用户通常将该农业化学组合物用于前剂量装置、小背包喷雾器、喷雾罐、喷雾飞机或灌溉***。通常将该农业化学组合物用水、缓冲剂和/或其他助剂配制至所需施用浓度,从而得到即用喷雾液或本发明农业化学组合物。每公顷农业利用区通常施用20-2000升,优选50-400升即用喷雾液。
化合物I、其N-氧化物和盐可以转化成农业化学组合物常用的类型,例如溶液、乳液、悬浮液、粉剂、粉末、糊、颗粒、模压品、胶囊及其混合物。组合物类型(参见“Catalogueof pesticide formulation types and international coding system”,TechnicalMonograph,第2期,2008年5月第6版,CropLife International)的实例是悬浮液(SC、OD、FS),可乳化浓缩物(EC),乳液(EW、EO、ES、ME),胶囊(例如CS、ZC),糊,锭剂,可湿性粉末或粉剂(WP、SP、WS、DP、DS),模压品(例如BR、TB、DT),颗粒(例如WG、SG、GR、FG、GG、MG),杀虫制品(例如LN)以及处理植物繁殖材料如种子的凝胶配制剂(例如GF)。组合物如Mollet和Grubemann,Formulation technology,Wiley VCH,Weinheim,2001;或Knowles,Newdevelopments in crop protection product formulation,Agrow Reports DS243,T&FInforma,London,2005所述以已知方式制备。本发明还涉及包含助剂和至少一种化合物I的农业化学组合物。合适的助剂是溶剂,液体载体,固体载体或填料,表面活性剂,分散剂,乳化剂,润湿剂,辅助剂,加溶剂,渗透促进剂,保护性胶体,粘附剂,增稠剂,保湿剂,驱除剂,引诱剂,进食刺激剂,相容剂,杀菌剂,防冻剂,消泡剂,着色剂,增粘剂和粘合剂。
农业化学组合物通常包含0.01-95重量%,优选0.1-90重量%,更优选1-70重量%,尤其是10-60重量%活性物质(例如至少一种化合物I)。此外,农业化学组合物通常包含5-99.9重量%,优选10-99.9重量%,更优选30-99重量%,尤其是40-90重量%至少一种助剂。
当用于植物保护中时,活性物质的施用量取决于所需效果的种类为0.001-2kg/ha,优选0.005-2kg/ha,更优选0.05-0.9kg/ha,尤其是0.1-0.75kg/ha。
在植物繁殖材料如种子例如通过撒粉、包衣或浸透的处理中,通常要求活性物质的量为0.1-1000g/100kg,优选1-1000g/100kg,更优选1-100g/100kg,最优选5-100g/100kg植物繁殖材料(优选种子)。
可以向化合物I或其组合物中作为预混物加入或者在紧临使用前加入(桶混合)各种类型的油、润湿剂、辅助剂、肥料或微营养素和其他农药(例如杀真菌剂、生长调节剂、除草剂、杀虫剂、安全剂)。这些试剂可以以1:100-100:1,优选1:10-10:1的重量比与本发明组合物混合。
将化合物I或包含它们的组合物以杀真菌剂的使用形式与其他杀真菌剂混合在许多情况下拓宽杀真菌活性谱或防止杀真菌剂抗药性的产生。此外,在许多情况下得到协同增效作用(协同增效混合物)。
化合物I可以与其一起使用的下列农药II用来说明可能的组合,但不限制它们:
A)呼吸抑制剂
-Qo位点的配合物III抑制剂:腈嘧菌酯(A.1.1)、甲香菌酯(coumethoxystrobin)(A.1.2)、丁香菌酯(coumoxystrobin)(A.1.3)、醚菌胺(A.1.4)、烯肟菌酯(enestroburin)(A.1.5)、烯肟菌胺(fenaminstrobin)(A.1.6)、fenoxystrobin/氟菌螨酯(flufenoxystrobin)(A.1.7)、氟嘧菌酯(fluoxastrobin)(A.1.8)、亚胺菌(kresoxim-methyl)(A.1.9)、mandestrobin(A.1.10)、叉氨苯酰胺(A.1.11)、肟醚菌胺(A.1.12)、啶氧菌酯(A.1.13)、唑菌胺酯(A.1.14)、唑胺菌酯(pyrametostrobin)(A.1.15)、唑菌酯(pyraoxystrobin)(A.1.16)、肟菌酯(A.1.17)、2-(2-(3-(2,6-二氯苯基)-1-甲基亚烯丙基氨基氧甲基)苯基)-2-甲氧亚氨基-N-甲基乙酰胺(A.1.18)、pyribencarb(A.1.19)、氯啶菌酯(triclopyricarb)/chlorodincarb(A.1.20)、唑酮菌(famoxadone)(A.1.21)、咪唑菌酮(fenamidone)(A.1.21)、N-[2-[(1,4-二甲基-5-苯基吡唑-3-基)氧基甲基]苯基]-N-甲氧基氨基甲酸甲酯(A.1.22)、metyltetraprole(A.1.25)、(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧亚氨基-N,3-二甲基戊-3-烯酰胺(A.1.34)、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧亚氨基-N,3-二甲基戊-3-烯酰胺(A.1.35)、嘧螨胺(pyriminostrobin)(A.1.36)、吡氟菌酯(bifujunzhi)(A.1.37)、2-(邻-((2,5-二甲基苯基氧亚甲基)苯基)-3-甲氧基丙烯酸甲酯(A.1.38);
-Qi位点的配合物III抑制剂:氰霜唑(cyazofamid)(A.2.1)、吲唑磺菌胺(amisulbrom)(A.2.2)、2-甲基丙酸[(6S,7R,8R)-8-苄基-3-[(3-羟基-4-甲氧基吡啶-2-羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧壬环-7-基]酯(A.2.3)、fenpicoxamid(A.2.4)、吡啶菌酰胺(florylpicoxamid)(A.2.5)、metarylpicoxamid(A.2.6);
-配合物II抑制剂:麦锈灵(benodanil)(A.3.1)、苯并烯氟菌唑(benzovindiflupyr)(A.3.2)、联苯吡菌胺(bixafen)(A.3.3)、啶酰菌胺(boscalid)(A.3.4)、萎锈灵(carboxin)(A.3.5)、呋菌胺(fenfuram)(A.3.6)、氟吡菌酰胺(fluopyram)(A.3.7)、氟酰胺(flutolanil)(A.3.8)、氟唑菌酰胺(fluxapyroxad)(A.3.9)、呋吡唑灵(furametpyr)(A.3.10)、isofetamid(A.3.11)、吡唑萘菌胺(isopyrazam)(A.3.12)、丙氧灭绣胺(mepronil)(A.3.13)、氧化萎锈灵(oxycarboxin)(A.3.14)、氟唑菌苯胺(penflufen)(A.3.15)、吡噻菌胺(penthiopyrad)(A.3.16)、氟唑菌酰羟胺(pydiflumetofen)(A.3.17)、联苯吡嗪菌胺(pyraziflumid)(A.3.18)、氟唑环菌胺(sedaxane)(A.3.19)、叶枯酞(tecloftalam)(A.3.20)、溴氟唑菌(thifluzamide)(A.3.21)、inpyrfluxam(A.3.22)、pyrapropoyne(A.3.23)、氟茚唑菌胺(fluindapyr)(A.3.28)、N-[2-[2-氯-4-三氟甲基苯氧基]苯基]-3-二氟甲基-5-氟-1-甲基吡唑-4-甲酰胺(A.3.29)、(E)-2-[2-[(5-氰基-2-甲基苯氧基)甲基]苯基]-3-甲氧基丙-2-烯酸甲酯(A.3.30)、isoflucypram(A.3.31)、2-二氟甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡啶-3-甲酰胺(A.3.32)、2-二氟甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢化茚-4-基]吡啶-3-甲酰胺(A.3.33)、2-二氟甲基-N-(3-乙基-1,1-二甲基-2,3-二氢化茚-4-基)吡啶-3-甲酰胺(A.3.34)、2-二氟甲基-N-[(3R)-3-乙基-1,1-二甲基-2,3-二氢化茚-4-基]吡啶-3-甲酰胺(A.3.35)、2-二氟甲基-N-(1,1-二甲基-3-丙基-2,3-二氢化茚-4-基)吡啶-3-甲酰胺(A.3.36)、2-二氟甲基-N-[(3R)-1,1-二甲基-3-丙基-2,3-二氢化茚-4-基]吡啶-3-甲酰胺(A.3.37)、2-二氟甲基-N-(3-异丁基-1,1-二甲基-2,3-二氢化茚-4-基)吡啶-3-甲酰胺(A.3.38)、2-二氟甲基-N-[(3R)-3-异丁基-1,1-二甲基-2,3-二氢化茚-4-基]吡啶-3-甲酰胺(A.3.39)、cyclobutrifluram(A.3.24);
-其他呼吸抑制剂:二氟林(diflumetorim)(A.4.1);硝基苯基衍生物:乐杀螨(binapacryl)(A.4.2)、敌螨通(dinobuton)(A.4.3)、敌螨普(dinocap)(A.4.4)、氟啶胺(fluazinam)(A.4.5)、消螨多(meptyldinocap)(A.4.6)、嘧菌腙(ferimzone)(A.4.7);有机金属化合物:三苯锡基盐,如薯瘟锡(fentin-acetate)(A.4.8)、三苯锡氯(fentinchloride)(A.4.9)或毒菌锡(fentin hydroxide)(A.4.10);唑嘧菌胺(ametoctradin)(A.4.11);硅噻菌胺(silthiofam)(A.4.12);
B)甾醇生物合成抑制剂(SBI杀真菌剂)
-C14脱甲基酶抑制剂:***类:戊环唑(azaconazole)(B.1.1)、双苯***醇(bitertanol)(B.1.2)、糠菌唑(bromuconazole)(B.1.3)、环唑醇(cyproconazole)(B.1.4)、醚唑(difenoconazole)(B.1.5)、烯唑醇(diniconazole)(B.1.6)、烯唑醇M(diniconazole-M)(B.1.7)、氧唑菌(epoxiconazole)(B.1.8)、腈苯唑(fenbuconazole)(B.1.9)、喹唑菌酮(fluquinconazole)(B.1.10)、氟硅唑(flusilazole)(B.1.11)、粉唑醇(flutriafol)(B.1.12)、己唑醇(hexaconazole)(B.1.13)、酰胺唑(imibenconazole)(B.1.14)、环戊唑醇(ipconazole)(B.1.15)、环戊唑菌(metconazole)(B.1.17)、腈菌唑(myclobutanil)(B.1.18)、oxpoconazole(B.1.19)、多效唑(paclobutrazole)(B.1.20)、戊菌唑(penconazole)(B.1.21)、丙环唑(propiconazole)(B.1.22)、丙硫菌唑(prothioconazole)(B.1.23)、硅氟唑(simeconazole)(B.1.24)、戊唑醇(tebuconazole)(B.1.25)、氟醚唑(tetraconazole)(B.1.26)、***酮(triadimefon)(B.1.27)、唑菌醇(triadimenol)(B.1.28)、戊叉唑菌(triticonazole)(B.1.29)、烯效唑(uniconazole)(B.1.30)、2-(2,4-二氟苯基)-1,1-二氟-3-(四唑-1-基)-1-[5-[4-(2,2,2-三氟乙氧基)苯基]-2-吡啶基]丙-2-醇(B.1.31)、2-(2,4-二氟苯基)-1,1-二氟-3-(四唑-1-基)-1-[5-[4-(三氟甲氧基)苯基]-2-吡啶基]丙-2-醇(B.1.32)、fluooxytioconazole(B.1.33)、ipfentrifluconazole(B.1.37)、氯氟醚菌唑(mefentrifluconazole)(B.1.38)、(2R)-2-[4-(4-氯苯氧基)-2-三氟甲基苯基]-1-(1,2,4-***-1-基)丙-2-醇、(2S)-2-[4-(4-氯苯氧基)-2-三氟甲基苯基]-1-(1,2,4-***-1-基)丙-2-醇、2-氯甲基-2-甲基-5-(对甲苯基甲基)-1-(1,2,4-***-1-基甲基)环戊醇(B.1.43);咪唑类:抑霉唑(imazalil)(B.1.44)、稻瘟酯(pefurazoate)(B.1.45)、丙氯灵(prochloraz)(B.1.46)、氟菌唑(triflumizol)(B.1.47);嘧啶类、吡啶类、哌嗪类:异嘧菌醇(fenarimol)(B.1.49)、啶斑肟(pyrifenox)(B.1.50)、嗪氨灵(triforine)(B.1.51)、[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)异唑-4-基]-(3-吡啶基)甲醇(B.1.52)、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-***-1-基)丙基]-3-吡啶基]氧基]苄腈(B.1.53)、2-[6-(4-溴苯氧基)-2-三氟甲基-3-吡啶基]-1-(1,2,4-***-1-基)丙-2-醇(B.1.54)、2-[6-(4-氯苯氧基)-2-三氟甲基-3-吡啶基]-1-(1,2,4-***-1-基)丙-2-醇(B.1.55);
-Δ14-还原酶抑制剂:4-十二烷基-2,6-二甲基吗啉(aldimorph)(B.2.1)、吗菌灵(dodemorph)(B.2.2)、吗菌灵乙酸酯(dodemorph-acetate)(B.2.3)、丁苯吗啉(fenpropimorph)(B.2.4)、克啉菌(tridemorph)(B.2.5)、苯锈啶(fenpropidin)(B.2.6)、粉病灵(piperalin)(B.2.7)、螺茂胺(spiroxamine)(B.2.8);
-3-酮基还原酶抑制剂:环酰菌胺(fenhexamid)(B.3.1);
-其他甾醇生物合成抑制剂:氯苯肟唑(chlorphenomizole)(B.4.1);
C)核酸合成抑制剂
-苯基酰胺类或酰基氨基酸类杀真菌剂:苯霜灵(benalaxyl)(C.1.1)、精苯霜灵(benalaxyl-M)(C.1.2)、kiralaxyl(C.1.3)、甲霜灵(metalaxyl)(C.1.4)、精甲霜灵(metalaxyl-M)(C.1.5)、甲呋酰胺(ofurace)(C.1.6)、霜灵(oxadixyl)(C.1.7);
-其他核酸合成抑制剂:土菌消(hymexazole)(C.2.1)、异噻菌酮(octhilinone)(C.2.2)、恶喹酸(oxolinic acid)(C.2.3)、磺嘧菌灵(bupirimate)(C.2.4)、5-氟胞嘧啶(C.2.5)、5-氟-2-(对甲苯基甲氧基)嘧啶-4-胺(C.2.6)、5-氟-2-(4-氟苯基甲氧基)嘧啶-4-胺(C.2.7)、5-氟-2-(4-氯苯基甲氧基)嘧啶-4-胺(C.2.8);
D)细胞***和细胞骨架抑制剂
-微管蛋白抑制剂:苯菌灵(benomyl)(D1.1)、多菌灵(carbendazim)(D1.2)、麦穗宁(fuberidazole)(D1.3)、涕必灵(thiabendazole)(D1.4)、甲基托布津(thiophanate-methyl)(D1.5)、pyridachlometyl(D.1.6)、N-乙基-2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]丁酰胺(D.1.8)、N-乙基-2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-2-甲硫基乙酰胺(D.1.9)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-N-(2-氟乙基)丁酰胺(D.1.10)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-N-(2-氟乙基)-2-甲氧基乙酰胺(D.1.11)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-N-丙基丁酰胺(D.1.12)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-2-甲氧基-N-丙基乙酰胺(D.1.13)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-2-甲硫基-N-丙基乙酰胺(D.1.14)、2-[(3-乙炔基-8-甲基-6-喹啉基)氧基]-N-(2-氟乙基)-2-甲硫基乙酰胺(D.1.15)、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-2,5-二甲基吡唑-3-胺(D.1.16);
-其他细胞***抑制剂:乙霉威(diethofencarb)(D.2.1)、噻唑菌胺(ethaboxam)(D.2.2)、戊菌隆(pencycuron)(D.2.3)、氟吡菌胺(fluopicolide)(D.2.4)、苯酰菌胺(zoxamide)(D.2.5)、苯菌酮(metrafenone)(D.2.6)、pyriofenone(D.2.7)、氰烯菌酯(phenamacril)(D.2.8);
E)氨基酸和蛋白质合成抑制剂
-蛋氨酸合成抑制剂:环丙嘧啶(cyprodinil)(E.1.1)、嘧菌胺(mepanipyrim)(E.1.2)、二甲嘧菌胺(pyrimethanil)(E.1.3);
-蛋白质合成抑制剂:灭瘟素(blasticidin-S)(E.2.1)、春雷素(kasugamycin)(E.2.2)、水合春雷素(kasugamycin hydrochloride-hydrate)(E.2.3)、米多霉素(mildiomycin)(E.2.4)、链霉素(streptomycin)(E.2.5)、土霉素(oxytetracyclin)(E.2.6);
F)信号转导抑制剂
-MAP/组氨酸激酶抑制剂:氟菌安(fluoroimid)(F.1.1)、异丙定(iprodione)(F.1.2)、杀菌利(procymidone)(F.1.3)、烯菌酮(vinclozolin)(F.1.4)、氟菌(fludioxonil)(F.1.5);
-G蛋白抑制剂:喹氧灵(quinoxyfen)(F.2.1);
G)类脂和膜合成抑制剂
-磷脂生物合成抑制剂:克瘟散(edifenphos)(G.1.1)、异稻瘟净(iprobenfos)(G.1.2)、定菌磷(pyrazophos)(G.1.3)、稻瘟灵(isoprothiolane)(G.1.4);
-类脂过氧化:氯硝胺(dicloran)(G.2.1)、五氯硝基苯(quintozene)(G.2.2)、四氯硝基苯(tecnazene)(G.2.3)、甲基立枯磷(tolclofos-methyl)(G.2.4)、联苯(G.2.5)、地茂散(chloroneb)(G.2.6)、氯唑灵(etridiazole)(G.2.7)、噻唑锌(zinc thiazole)(G.2.8);
-磷脂生物合成和细胞壁沉积:烯酰吗啉(dimethomorph)(G.3.1)、氟吗啉(flumorph)(G.3.2)、双炔酰菌胺(mandipropamid)(G.3.3)、丁吡吗啉(pyrimorph)(G.3.4)、苯噻菌胺(benthiavalicarb)(G.3.5)、异丙菌胺(iprovalicarb)(G.3.6)、valifenalate(G.3.7);
-影响细胞膜渗透性的化合物和脂肪酸:百维灵(propamocarb)(G.4.1);
-氧化甾醇结合蛋白抑制剂:氟噻唑吡乙酮(oxathiapiprolin)(G.5.1)、fluoxapiprolin(G.5.3)、4-[1-[2-[3-二氟甲基-5-甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.4)、4-[1-[2-[3,5-二(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.5)、4-[1-[2-[3-二氟甲基-5-三氟甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.6)、4-[1-[2-[5-环丙基-3-二氟甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.7)、4-[1-[2-[5-甲基-3-三氟甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.8)、4-[1-[2-[5-二氟甲基-3-三氟甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.9)、4-[1-[2-[3,5-二(三氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.10)、(4-[1-[2-[5-环丙基-3-三氟甲基吡唑-1-基]乙酰基]-4-哌啶基]-N-四氢萘-1-基吡啶-2-甲酰胺(G.5.11);
H)具有多位点作用的抑制剂
-无机活性物质:波尔多液(Bordeaux混合物)(H.1.1)、铜(H.1.2)、醋酸铜(H.1.3)、氢氧化铜(H.1.4)、王铜(copper oxychloride)(H.1.5)、碱式硫酸铜(H.1.6)、硫(H.1.7);
-硫代-和二硫代氨基甲酸酯类:福美铁(ferbam)(H.2.1)、代森锰锌(mancozeb)(H.2.2)、代森锰(maneb)(H.2.3)、威百亩(metam)(H.2.4)、代森联(metiram)(H.2.5)、甲基代森锌(propineb)(H.2.6)、福美双(thiram)(H.2.7)、代森锌(zineb)(H.2.8)、福美锌(ziram)(H.2.9);
-有机氯化合物:敌菌灵(anilazine)(H.3.1)、百菌清(chlorothalonil)(H.3.2)、敌菌丹(captafol)(H.3.3)、克菌丹(captan)(H.3.4)、灭菌丹(folpet)(H.3.5)、抑菌灵(dichlofluanid)(H.3.6)、双氯酚(dichlorophen)(H.3.7)、六氯苯(H.3.8)、五氯酚(pentachlorphenole)(H.3.9)及其盐、四氯苯酞(phthalide)(H.3.10)、对甲抑菌灵(tolylfluanid)(H.3.11);
-胍类及其他:胍(H.4.1)、多果定(H.4.2)、多果定游离碱(H.4.3)、双胍盐(guazatine)(H.4.4)、双胍辛胺(guazatine-acetate)(H.4.5)、双胍辛醋酸盐(iminoctadine)(H.4.6)、双胍辛胺三乙酸盐(iminoctadine-triacetate)(H.4.7)、双八胍盐(iminoctadine-tris(albesilate))(H.4.8)、二噻农(dithianon)(H.4.9)、2,6-二甲基-1H,5H-[1,4]二噻二烯并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮(H.4.10);
I)细胞壁合成抑制剂
-葡聚糖合成抑制剂:井冈霉素(validamycin)(I.1.1)、多氧霉素(polyoxin B)(I.1.2);
-黑素合成抑制剂:咯喹酮(pyroquilon)(I.2.1)、三环唑(tricyclazole)(I.2.2)、氯环丙酰胺(carpropamid)(I.2.3)、双氯氰菌胺(dicyclomet)(I.2.4)、氰菌胺(fenoxanil)(I.2.5);
J)植物防御诱发剂
-噻二唑素(acibenzolar-S-methyl)(J.1.1)、噻菌灵(probenazole)(J.1.2)、异噻菌胺(isotianil)(J.1.3)、噻酰菌胺(tiadinil)(J.1.4)、调环酸钙(prohexadione-calcium)(J.1.5);膦酸酯类:藻菌磷(fosetyl)(J.1.6)、乙磷铝(fosetyl-aluminum)(J.1.7)、亚磷酸及其盐(J.1.8)、膦酸钙(J.1.11)、膦酸钾(J.1.12)、碳酸氢钾或钠(J.1.9)、4-环丙基-N-(2,4-二甲氧基苯基)噻二唑-5-甲酰胺(J.1.10);
K)未知作用模式
-拌棉醇(bronopol)(K.1.1)、灭螨蜢(chinomethionat)(K.1.2)、环氟菌胺(cyflufenamid)(K.1.3)、清菌脲(cymoxanil)(K.1.4)、棉隆(dazomet)(K.1.5)、咪菌威(debacarb)(K.1.6)、双氯氰菌胺(diclocymet)(K.1.7)、哒菌清(diclomezine)(K.1.8)、野燕枯(difenzoquat)(K.1.9)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)(K.1.10)、二苯胺(K.1.11)、杀螟松(fenitropan)(K.1.12)、胺苯吡菌酮(fenpyrazamine)(K.1.13)、氟联苯菌(flumetover)(K.1.14)、flumetylsulforim(K.1.60)、磺菌胺(flusulfamide)(K.1.15)、flutianil(K.1.16)、超敏蛋白(harpin)(K.1.17)、磺菌威(methasulfocarb)(K.1.18)、氯定(nitrapyrin)(K.1.19)、异丙消(nitrothal-isopropyl)(K.1.20)、tolprocarb(K.1.21)、喹啉铜(oxin-copper)(K.1.22)、丙氧喹啉(proquinazid)(K.1.23)、辛菌胺(seboctylamine)(K.1.61)、tebufloquin(K.1.24)、叶枯酞(K.1.25)、唑菌嗪(triazoxide)(K.1.26)、N'-(4-(4-氯-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒(K.1.27)、N'-(4-(4-氟-3-三氟甲基苯氧基)-2,5-二甲基苯基)-N-乙基-N-甲基甲脒(K.1.28)、N'-[4-[[3-[(4-氯苯基)甲基]-1,2,4-噻二唑-5-基]氧基]-2,5-二甲基苯基]-N-乙基-N-甲基甲脒(K.1.29)、N'-(5-溴-6-(2,3-二氢化茚-2-基)氧基-2-甲基-3-吡啶基)-N-乙基-N-甲基甲脒(K.1.30)、N'-[5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基-3-吡啶基]-N-乙基-N-甲基甲脒(K.1.31)、N'-[5-溴-6-(4-异丙基环己氧基)-2-甲基-3-吡啶基]-N-乙基-N-甲基甲脒(K.1.32)、N'-[5-溴-2-甲基-6-(1-苯基乙氧基)-3-吡啶基]-N-乙基-N-甲基甲脒(K.1.33)、N'-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒(K.1.34)、N'-(5-二氟甲基-2-甲基-4-(3-三甲基硅烷基丙氧基)苯基)-N-乙基-N-甲基甲脒(K.1.35)、2-(4-氯苯基)-N-[4-(3,4-二甲氧基苯基)异唑-5-基]-2-丙-2-炔氧基乙酰胺(K.1.36)、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶(pyrisoxazole)(K.1.37)、3-[5-(4-甲基苯基)-2,3-二甲基异唑烷-3-基]吡啶(K.1.38)、5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑(K.1.39)、(Z)-3-氨基-2-氰基-3-苯基丙-2-烯酸乙酯(K.1.40)、四唑吡氨酯(picarbutrazox)(K.1.41)、N-[6-[[(Z)-[(1-甲基四唑-5-基)苯基亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸戊酯(K.1.42)、N-[6-[[(Z)-[(1-甲基四唑-5-基)苯基亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸丁-3-炔基酯(K.1.43)、ipflufenoquin(K.1.44)、quinofumelin(K.1.47)、噻霉酮(benzothiazolinone)(K.1.48)、溴菌腈(bromothalonil)(K.1.49)、2-(6-苄基-2-吡啶基)喹唑啉(K.1.50)、2-[6-(3-氟-4-甲氧基苯基)-5-甲基-2-吡啶基]喹唑啉(K.1.51)、dichlobentiazox(K.1.52)、N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基甲脒(K.1.53)、aminopyrifen(K.1.54)、氟醚菌酰胺(fluopimomide)(K.1.55)、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基乙氧基)-3-吡啶基]-N-乙基-N-甲基甲脒(K.1.56)、N'-[4-(4,5-二氯噻唑-2-基)氧基-2,5-二甲基苯基]-N-乙基-N-甲基甲脒(K.1.57)、flufenoxadiazam(K.1.58)、N-甲基-4-[5-三氟甲基-1,2,4-二唑-3-基]苯硫代甲酰胺(K.1.59)、N-甲氧基-N-[[4-[5-三氟甲基-1,2,4-二唑-3-基]苯基]甲基]环丙烷甲酰胺(WO2018/177894,WO 2020/212513);
在二元混合物中,组分1)和组分2)的重量比通常取决于所用组分的性能,它通常在1:10,000-10,000:1范围内,常常是1:100-100:1,经常是1:50-50:1,优选1:20-20:1,更优选1:10-10:1,甚至更优选1:4-4:1,尤其是1:2-2:1。根据其他实施方案,组分1)和组分2)的重量比通常在1000:1-1:1范围内,常常是100:1-1:1,经常是50:1-1:1,优选20:1-1:1,更优选10:1-1:1,甚至更优选4:1-1:1,尤其是2:1-1:1。根据其他实施方案,组分1)和组分2)的重量比通常在20,000:1-1:10范围内,常常是10,000:1-1:1,经常是5,000:1-5:1,优选5,000:1-10:1,更优选2,000:1-30:1,甚至更优选2,000:1-100:1,尤其是1,000:1-100:1。根据其他实施方案,组分1)和组分2)的重量比通常在1:1-1:1000范围内,常常是1:1-1:100,经常是1:1-1:50,优选1:1-1:20,更优选1:1-1:10,甚至更优选1:1-1:4,尤其是1:1-1:2。根据其他实施方案,组分1)和组分2)的重量比通常在10:1-1:20,000范围内,常常是1:1-1:10,000,经常是1:5-1:5,000,优选1:10-1:5,000,更优选1:30-1:2,000,甚至更优选1:100-1:2,000,尤其是1:100-1:1,000。
在三元混合物,即包含组分1)和组分2)以及化合物III(组分3)的组合物中,组分1)和组分2)的重量比取决于所用活性物质的性能,它通常在1:100-100:1范围内,经常是1:50-50:1,优选1:20-20:1,更优选1:10-10:1,尤其是1:4-4:1,并且组分1)和组分3)的重量比通常在1:100-100:1范围内,经常是1:50-50:1,优选1:20-20:1,更优选1:10-10:1,尤其是1:4-4:1。需要的话,将任何其他活性组分以20:1-1:20的比例加入组分1)中。这些比例还适合通过种子处理施用的混合物。
优选包含至少一种选自A)组中Qo位点的配合物III抑制剂,更优选选自化合物(A.1.1)、(A.1.4)、(A.1.8)、(A.1.9)、(A.1.10)、(A.1.12)、(A.1.13)、(A.1.14)、(A.1.17)、(A.1.21)、(A.1.25)、(A.1.34)和(A.1.35);特别是选自(A.1.1)、(A.1.4)、(A.1.8)、(A.1.9)、(A.1.13)、(A.1.14)、(A.1.17)、(A.1.25)、(A.1.34)和(A.1.35)的活性物质作为组分2)的混合物。
还优选包含至少一种选自A)组中Qi位点的配合物III抑制剂,更优选选自化合物(A.2.1)、(A.2.3)、(A.2.4)和(A.2.6);特别是选自(A.2.3)、(A.2.4)和(A.2.6)的活性物质作为组分2)的混合物。
还优选包含至少一种选自A)组中配合物II抑制剂,更优选选自化合物(A.3.2)、(A.3.3)、(A.3.4)、(A.3.7)、(A.3.9)、(A.3.11)、(A.3.12)、(A.3.15)、(A.3.16)、(A.3.17)、(A.3.18)、(A.3.19)、(A.3.20)、(A.3.21)、(A.3.22)、(A.3.23)、(A.3.24)、(A.3.28)、(A.3.31)、(A.3.32)、(A.3.33)、(A.3.34)、(A.3.35)、(A.3.36)、(A.3.37)、(A.3.38)和(A.3.39);特别是选自(A.3.2)、(A.3.3)、(A.3.4)、(A.3.7)、(A.3.9)、(A.3.12)、(A.3.15)、(A.3.17)、(A.3.19)、(A.3.22)、(A.3.23)、(A.3.24)、(A.3.31)、(A.3.32)、(A.3.33)、(A.3.34)、(A.3.35)、(A.3.36)、(A.3.37)、(A.3.38)和(A.3.39)的活性物质作为组分2)的混合物。
还优选包含至少一种选自A)组中其他呼吸抑制剂,更优选选自化合物(A.4.5)和(A.4.11);尤其是(A.4.11)的活性物质作为组分2)的混合物。
还优选包含至少一种选自B)组中C14脱甲基酶抑制剂,更优选选自化合物(B.1.4)、(B.1.5)、(B.1.8)、(B.1.10)、(B.1.11)、(B.1.12)、(B.1.13)、(B.1.17)、(B.1.18)、(B.1.21)、(B.1.22)、(B.1.23)、(B.1.25)、(B.1.26)、(B.1.29)、(B.1.33)、(B.1.34)、(B.1.37)、(B.1.38)、(B.1.43)、(B.1.46)、(B.1.53)、(B.1.54)和(B.1.55);特别是选自(B.1.5)、(B.1.8)、(B.1.10)、(B.1.17)、(B.1.22)、(B.1.23)、(B.1.25)、(B.1.33)、(B.1.34)、(B.1.37)、(B.1.38)、(B.1.43)和(B.1.46)的活性物质作为组分2)的混合物。
还优选包含至少一种选自B)组中Δ14-还原酶抑制剂,更优选选自化合物(B.2.4)、(B.2.5)、(B.2.6)和(B.2.8);尤其是(B.2.4)的活性物质作为组分2)的混合物。
还优选包含至少一种选自C)组中苯基酰胺类和酰基氨基酸类杀真菌剂,更优选选自化合物(C.1.1)、(C.1.2)、(C.1.4)和(C.1.5);特别是选自(C.1.1)和(C.1.4)的活性物质作为组分2)的混合物。
还优选包含至少一种选自C)组中其他核酸合成抑制剂,更优选选自化合物(C.2.6)、(C.2.7)和(C.2.8)的活性物质作为组分2)的混合物。
还优选包含至少一种选自D)组,更优选选自化合物(D.1.1)、(D.1.2)、(D.1.5)、(D.2.4)和(D.2.6);特别是选自(D.1.2)、(D.1.5)和(D.2.6)的活性物质作为组分2)的混合物。
还优选包含至少一种选自E)组,更优选选自化合物(E.1.1)、(E.1.3)、(E.2.2)和(E.2.3);尤其是(E.1.3)的活性物质作为组分2)的混合物。
还优选包含至少一种选自F)组,更优选选自化合物(F.1.2)、(F.1.4)和(F.1.5)的活性物质作为组分2)的混合物。
还优选包含至少一种选自G)组,更优选选自化合物(G.3.1)、(G.3.3)、(G.3.6)、(G.5.1)、(G.5.3)、(G.5.4)、(G.5.5),G.5.6),G.5.7)、(G.5.8)、(G.5.9)、(G.5.10)和(G.5.11);特别是选自(G.3.1)、(G.5.1)和(G.5.3)的活性物质作为组分2)的混合物。
还优选包含至少一种选自H)组,更优选选自化合物(H.2.2)、(H.2.3)、(H.2.5)、(H.2.7)、(H.2.8)、(H.3.2)、(H.3.4)、(H.3.5)、(H.4.9)和(H.4.10);特别是选自(H.2.2)、(H.2.5)、(H.3.2)、(H.4.9)和(H.4.10)的活性物质作为组分2)的混合物。
还优选包含至少一种选自I)组,更优选选自化合物(I.2.2)和(I.2.5)的活性物质作为组分2)的混合物。
还优选包含至少一种选自J)组,更优选选自化合物(J.1.2)、(J.1.5)、(J.1.8)、(J.1.11)和(J.1.12);尤其是(J.1.5)的活性物质作为组分2)的混合物。
还优选包含至少一种选自K)组,更优选选自化合物(K.1.41)、(K.1.42)、(K.1.44)、(K.1.47)、(K.1.57)、(K.1.58)和(K.1.59);特别是选自(K.1.41)、(K.1.44)、(K.1.47)、(K.1.57)、(K.1.58)和(K.1.59)的活性物质作为组分2)的混合物。
包含活性成分的混合物的组合物可以通过常规手段制备,例如通过对化合物I的组合物所给手段制备。
实施例:
合成方法
实施例1:(2E)-2-[2-[[(E)-3-(2-氟苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯
步骤1:1-(2-氟苯基)乙酮肟
将1-(2-氟苯基)乙烯酮(10g,1.0eq)加入甲醇(300ml)中并加入羟胺盐酸盐(7.54g,1.8eq)。在25℃下滴加吡啶(33.45g,2eq)。将反应混合物在50℃下搅拌2小时。使用LCMS和TLC监测反应。在真空下蒸发甲醇。粗物质用水(200ml)稀释并将其用乙酸乙酯萃取(3×100ml)。再次用水和盐水洗涤合并的有机层。将有机层在硫酸钠上干燥并在真空下浓缩。粗化合物通过快速柱层析提纯。纯化合物用0%至20%在庚烷中的乙酸乙酯(EtOAc)洗脱。蒸发溶剂,以白色固体得到8g标题化合物(产率72%)。1H NMR 300MHz,DMSO-d6:δ11.4(s,1H),7.46-7.41(m,2H),7.27-7.23(m,2H),2.14(s,3H)。
步骤2:(2E)-2-[2-[[(E)-1-(2-氟苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸乙酯(实施例2)
将1-(2-氟苯基)乙酮肟(0.3g,3eq)加入二甲基甲酰胺(DMF,5ml)中并加入Cs2CO3(3.27g,2.0eq)。将反应混合物在室温(RT;约25℃)下搅拌30分钟,然后加入(2E)-2-[2-溴甲基-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯(0.6g,3.02eq)。将反应混合物在室温下搅拌32小时并通过TLC和LCMS监测。反应用水(45ml)猝灭并将产物在乙酸乙酯中萃取(3×35ml)。将合并的有机层用盐水(50ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用35-20%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂得到灰白色固体标题化合物(0.328g,45%产率)。1H NMR(300MHz,DMSO-d6):δ7.56-7.36(m,2H),7.33-7.32(m,4H),7.03(dd,J=6.2,2.8Hz,3H),5.00(s,2H),3.93(s,3H),3.64(s,3H),2.42(s,3H),2.08(d,J=2.5Hz,3H)。
实施例2:(2E)-2-[2-[[(E)-1-(2-氟苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基-N-甲基乙酰胺
将(2E)-2-[2-[[(E)-1-(2-氟苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯(实施例1;8g,1eq)加入THF(80ml)中并加入甲胺溶液(40%水溶液)(16ml,2vol)。将反应混合物在25℃下搅拌5小时并通过TLC和LCMS监测。反应用水(200ml)猝灭并将产物在乙酸乙酯中萃取(3×150ml)。将合并的有机层用盐水(150ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用30-40%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂得到白色固体标题化合物(7g,87.7%产率)。1H NMR(500MHz,DMSO-d6):δ8.20(q,J=4.7Hz,1H),7.44(ddt,J=7.8,5.6,2.0Hz,2H),7.37-7.14(m,4H),6.95(dd,J=7.1,2.0Hz,1H),5.01(s,2H),3.86(s,3H),2.65(d,J=4.8Hz,3H),2.42(s,3H),2.09(d,J=2.6Hz,3H)。
实施例3:(2E)-2-[2-[[(E)-1-(3,5-二氯苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯
步骤1:1-(3,5-二氯苯基)乙酮肟
将3-(3,5-二氯苯基)乙酮(3.0g,3eq)加入甲醇(30ml)中并加入NH2OH(0.735g,2eq),然后加入吡啶(3.04g,2.5eq)。将反应混合物加热至70℃并搅拌3小时。使用LCMS和TLC监测反应。蒸发溶剂并将残余物用水(50ml)稀释。产物用乙酸乙酯萃取(3×30ml)。将合并的有机层用盐水(50ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用15-20%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂得到白色固体化合物1-(3,5-二氯苯基)乙酮肟(1g,92.6%产率)。
步骤2:(2E)-2-[2-[[(E)-1-(3,5-二氯苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯
将3-(3,5-二氯苯基)乙酮肟(0.4g,1eq)加入乙腈(10ml)中并加入Cs2CO3(1.8g,2.5eq)。将反应混合物在室温下搅拌30分钟,然后加入(2E)-2-[2-溴甲基-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯(0.65g,1.05eq)。将反应混合物在室温下搅拌3小时并通过TLC和LCMS监测。反应用水(50ml)猝灭并将产物在乙酸乙酯中萃取(3×30ml)。将合并的有机层用盐水(50ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用20-25%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂得到灰白色固体标题化合物(0.6g,68%产率)。1H NMR(500MHz,DMSO-d6):δ7.66(t,J=1.9Hz,1H),7.61(d,J=1.9Hz,2H),7.36-7.23(m,2H),7.05-6.98(m,1H),5.04(s,2H),3.91(s,3H),3.70(s,3H),2.43(s,3H),2.30(s,3H)。
实施例4:(2E)-2-[2-[[(E)-1-(3,5-二氯苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基-N-甲基乙酰胺
将(2E)-2-[2-[[(E)-3-(3,5-二氯苯基)亚乙基氨基]氧基甲基]-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯(实施例3;0.6g,1eq)加入THF(6ml)中并加入甲胺溶液(40%水溶液)(1.2ml,2v)。将反应混合物在室温下搅拌3小时并通过TLC和LCMS监测。反应用水(25ml)猝灭并将产物在乙酸乙酯中萃取(3×20ml)。将合并的有机层用盐水(25ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用40-45%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂得到白色固体标题化合物(实施例2,0.53g,85%产率)。1H NMR(500MHz,DMSO-d6):δ8.24(d,J=4.8Hz,1H),7.69-7.58(m,3H),7.37-7.15(m,2H),6.95(dd,J=7.1,1.9Hz,1H),5.05(s,2H),3.86(s,3H),2.68(d,J=4.7Hz,3H),2.42(s,3H),2.11(s,3H)。
实施例5:(2E)-2-甲氧亚氨基-2-[3-甲基-2-[[(E)-1-对甲苯基亚乙基氨基]氧基甲基]苯基]乙酸甲酯
步骤1:1-对甲苯基乙酮肟
在室温和氮气气氛下向1-对甲苯基乙酮(1.0g,4.45mmol,3eq.)在甲醇(10ml)中的溶液中加入羟胺盐酸盐(0.77g,11.17mmol,1.5eq),然后加入乙酸钠(1.82g,15mmol,2eq.)。将反应混合物回流2小时。反应通过TLC监测。反应混合物在旋转蒸发仪上浓缩。向该粗残余物中加入水(20ml)并搅拌0.5小时。过滤并干燥固体物质,以白色固体得到纯标题化合物(1.1g,产率98%)。MS:[M+H]+150。
步骤2:(2E)-2-甲氧亚氨基-2-[3-甲基-1-[[(E)-3-对甲苯基亚乙基氨基]氧基甲基]苯基]乙酸甲酯
向1-对甲苯基乙酮肟(0.15g,1.0mmol,1eq)在乙腈(2mL)中的搅拌溶液中加入Cs2CO3(0.66g,2.0mmol,2eq)。将反应混合物在25℃下搅拌30分钟。然后加入(2E)-2-[2-溴甲基-3-甲基苯基]-2-甲氧亚氨基乙酸甲酯(0.33g,1.1mmol,1.1eq)。将该混合物在25℃下搅拌6小时。反应通过TLC和LCMS监测。向该反应混合物中加入水(30ml)并用EtOAc萃取(3×30ml)。合并的有机层用H2O洗涤(2×25ml),然后用盐水洗涤(2×20ml)。将有机层在Na2SO4上干燥并浓缩而得到粗化合物,后者通过使用0-20%在庚烷中的EtOAc作为洗脱剂的快速柱层析进一步提纯而以白色固体得到纯标题化合物(0.37g,产率96%)。1H NMR(500MHz,氯仿-d):δ7.42(d,J=8.2Hz,2H),7.26-7.19(m,3H),7.07(d,J=8.0Hz,2H),6.94(dd,J=7.2,1.8Hz,2H),5.03(s,2H),3.94(s,3H),3.70(s,3H),2.41(s,3H),2.27(s,3H),2.06(s,3H)。MS:[M+H]+369。
实施例6:(2E)-2-甲氧亚氨基-N-甲基-2-[3-甲基-2-[[(E)-1-对甲苯基亚乙基氨基]氧基甲基]苯基]乙酰胺
在RT下向(2E)-2-甲氧亚氨基-2-[3-甲基-1-[[(E)-3-对甲苯基亚乙基氨基]氧基甲基]苯基]乙酸甲酯在THF(5ml)中的搅拌溶液中加入甲胺水溶液(5.0mL,40%)。继续反应1小时。反应通过TLC监测。反应混合物在旋转蒸发仪上蒸发,残余物用EtOAc(20ml)稀释并用1N HCl洗涤(3×20ml),然后用盐水洗涤(2×20ml)。将有机层在Na2SO4上干燥并浓缩而得到粗化合物,后者通过使用0-50%在庚烷中的EtOAc作为洗脱剂的快速柱层析进一步提纯而以白色固体得到纯标题化合物(0.200g,产率88%)。1H NMR(500MHz,DMSO-d6):δ8.20(d,J=5.0Hz,1H),7.54-7.48(m,2H),7.31-7.22(m,2H),7.19(d,J=8.0Hz,2H),6.95(dd,J=6.9,2.1Hz,1H),4.99(s,2H),3.86(s,3H),2.69(d,J=4.7Hz,3H),2.43(s,3H),2.31(s,3H),2.08(s,3H)。MS:[M+H]+368。
实施例7:(2E)-2-甲氧亚氨基-N-甲基-2-[3-甲基-2-[[(E)-[3,3,3-三氟-1-[3-三氟甲基苯基]亚丙基]氨基]氧基甲基]苯基]乙酰胺
将类似于现有技术方法(Chem Commun,2016,52,13668-13670)制备的3,3,3-三氟-1-[3-三氟甲基苯基]丙-1-酮(0.5g,1eq)加入THF(10ml)中并加入(2E)-2-[2-(氨基氧基甲基)-3-甲基苯基]-2-甲氧亚氨基-N-甲基乙酰胺(0.98g,2eq),然后加入Ti(OEt)4(1.33g,3eq)。将该混合物加热至70℃并搅拌12小时。该反应通过TLC和LCMS监测。该反应用水(25ml)猝灭,然后用EtOAc(25ml)猝灭。将形成的乳液滤过硅藻土并用EtOAc(50ml)洗涤。分离各层并在EtOAc中萃取水层(2×25ml)。将合并的有机层用盐水(25ml)洗涤,在硫酸钠上干燥并在真空下浓缩。粗物质通过快速层析提纯。通过使用40-45%在庚烷中的EtOAc洗脱纯化合物。蒸发溶剂并随后在庚烷中结晶得到灰白色固体(0.34g,35%产率)。
1H NMR(500MHz,DMSO-d6):δ8.27(q,J=4.7Hz,1H),8.07-8.00(m,2H),7.85-7.79(m,1H),7.68(t,J=7.8Hz,1H),7.35-7.24(m,2H),6.97(dd,J=7.3,1.7Hz,1H),5.12(s,2H),4.03-3.96(q,J=10Hz,2H),3.86(s,3H),2.67(d,J=4.7Hz,3H),2.43(s,3H)。
表S中的下列实施例按照上述通用方案1合成(实施例7和212除外,它们按照方案2合成)并由如表L所述的LCMS表征。
表L:LCMS方法
表S中使用的LCMS方法在LCMS栏找到。
表S:
生物学研究
温室和离体叶片试验
将该化合物溶于溶剂/乳化剂比例(体积)为99/1的丙酮和/或二甲亚砜和基于乙氧基化烷基酚的润湿剂/乳化剂Wettol的混合物中,得到5ml的总体积。然后加入水至总体积为100ml。然后用所述溶剂-乳化剂-水混合物稀释该储备溶液至下表中给出的最终浓度。
应用实施例1.在大豆上对由豆薯层锈菌引起的大豆锈病的治疗性防治(PHAKPAK4)
对盆栽大豆秧苗的叶片接种豆薯层锈菌的孢子。所用菌株在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L。为了确保人工接种成功,将植株转移至相对湿度约95%和20-24℃的潮湿室中达24小时。第二天将植株在温室中于23-27℃和60-80%的相对湿度下栽培3天。然后用含有浓度如下所述的活性成分或混合物的前述喷雾溶液将植株喷雾至滴流。使植株风干。然后将试验植株在温室中于23-27℃和60-80%的相对湿度下栽培高达14天。以患病叶面积%肉眼评价叶片上的真菌侵袭程度,未处理对照的病害水平通常高于85%。
应用实施例2.在大豆上对由豆薯层锈菌引起的大豆锈病的保护性防治(PHAKPAP2)
用含有浓度如下所述的活性成分或混合物的前述喷雾溶液将盆栽大豆秧苗的叶片喷雾至滴流。使植株风干。将试验植株在温室中于23-27℃和60-80%的相对湿度下栽培2天。然后对植株接种豆薯层锈菌的孢子。所用菌株在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L。为了确保人工接种成功,将植株转移至相对湿度约95%和20-24℃的潮湿室中达24小时。然后将试验植株在温室中于23-27℃和60-80%的相对湿度下栽培高达14天。以患病叶面积%肉眼评价叶片上的真菌侵袭程度,未处理对照的病害水平通常高于85%。
应用实施例3.在大豆上对由豆薯层锈菌引起的大豆锈病的保护性防治(PHAKPAP6)
用含有浓度如下所述的活性成分的前述喷雾溶液将盆栽大豆秧苗的叶片喷雾至滴流。使植株风干。将试验植株在温室中于23-27℃和60-80%的相对湿度下栽培6天。然后对植株接种豆薯层锈菌的孢子。所用菌株在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L。为了确保人工接种成功,将植株转移至相对湿度约95%和23-27℃的潮湿室中达24小时。然后将试验植株在温室中于23-27℃和60-80%的相对湿度下栽培高达14天。以患病叶面积%肉眼评价叶片上的真菌侵袭程度,未处理对照的病害水平通常高于85%。
应用实施例4.在离体大豆叶片上对由豆薯层锈菌引起的大豆锈病的保护性防治(PHAKPA P1 DL)
用含有浓度如下所述的活性成分的前述喷雾溶液将盆栽大豆秧苗的叶片喷雾至滴流。将植株在温室中于20℃和14小时照明下干燥过夜。第二天收割叶片并将其放置在水琼脂板上。然后对叶片接种豆薯层锈菌的孢子。使用两种不同分离物:一种对Qo抑制剂敏感(wt);并且一种在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L(F129L)。在暗尘室中将接种叶片在室温下温育16-24小时,然后在温育箱中于20℃和12小时光/天下温育2-3周。以患病叶面积%肉眼评价叶片上的真菌侵袭程度。
微滴定板试验
将活性化合物分开在二甲亚砜中配制成浓度为10,000ppm的储备溶液。将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。
在加入如下面的不同应用实施例中所示的相应孢子悬浮液之后,将各板置于温度为18℃的水蒸气饱和室中。接种7天后使用吸收光度计在405nm下测量MTP。将测量参数与不含活性化合物的对照方案的生长(100%)和不含真菌的空白值相比较,以确定相应活性化合物中病原体的相对生长%。
应用实施例5.对引起稻瘟病的稻瘟病菌(Pyricularia oryzae)的活性(PYRIOR)
使用稻瘟病菌在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液的孢子悬浮液。
应用实施例6.对在小麦上引起叶枯病的小麦壳针孢的活性(SEPTTR)
使用小麦壳针孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液的孢子悬浮液。
应用实施例7.对引起炭疽病的南瓜炭疽病菌(Colletotrichum orbiculare)的活性(COLLLA)
使用南瓜炭疽病菌在2%麦芽水溶液中的孢子悬浮液。
应用实施例8.对引起小麦叶斑病的颖枯球腔菌(Leptosphaeria nodorum)的活性(LEPTNO)
使用颖枯球腔菌在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。
应用实施例9.对引起早疫病的早疫链格孢的活性(ALTESO,wt和F129L)
使用早疫链格孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的两种不同孢子悬浮液:敏感性野生型分离物(wt)和在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L(F129L)的Qo抑制剂耐受性分离物。
应用实施例10.对在大麦上引起网斑病的大麦网斑内脐蠕孢的活性(PYRNTE,wt和F129L)
使用大麦网斑内脐蠕孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的两种不同孢子悬浮液:敏感性野生型分离物(wt)和在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L(F129L)的Qo抑制剂耐受性分离物。
应用实施例11.对引起大豆大豆灰斑病的大豆灰斑病菌(Cercospora sojina)的活性(CERCSO)
然后加入大豆灰斑病菌在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。
应用实施例12.对引起雪霉病的雪霉叶枯菌(Microdochium nivale)的活性(MONGNI)
使用雪霉叶枯菌在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。
上述应用实施例的结果在下表中给出。
对于防治在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌给出下表1和C1-C4中的测试结果。
表1:
对比试验
表C1:
表C2:
表C3:
表C4:
表C1-C4中的结果表明与其中位置R3未被取代的化合物相比,在R3的特定取代基改善了对在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的杀真菌活性。
表C5:
表C6a:
表C6b:
表C5-C6b中的结果表明与使用WO 2017/157923中所公开的化合物相比,本发明化合物显著改善对在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的杀真菌活性。
表C7a:
表C7b:
表C8a:
表C8b:
表C7a-C8b中的结果表明与来自现有技术的化合物相比,末端苯基的特定取代基Ra改善了对植物病原性真菌的杀真菌活性。
表C9:
表C10:
表C11a:
表C11b:
表C12:
表C13:
表C14:
表C15a:
表C15b:
表C16a:
表C16b:
表C17:
表C18:
表C9-C18中的结果表明与来自现有技术的化合物相比,特定取代基R4改善了对植物病原性真菌的杀真菌活性。
Claims (15)
1.式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的用途:
其中
R1选自O和NH;
R2选自CH和N;
R3选自卤素、C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C6环烷基和-O-C1-C4烷基;
R4选自C1-C6烷基、C2-C4链烯基、C2-C4炔基、C1-C6卤代烷基、C2-C4卤代链烯基、C2-C4卤代炔基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)、-(C1-C2烷基)-O-(C1-C2卤代烷基)和-C1-C4烷基-C3-C6环烷基;
Ra选自卤素、CN、-NR5R6、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、-C(=O)-C1-C4烷基、-O-CH2-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,
并且其中Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的相同或不同基团Rb:
Rb选自卤素、CN、NH2、NO2、C1-C4烷基、C1-C4卤代烷基、-O-C1-C4烷基和-O-C1-C4卤代烷基;
R5、R6相互独立地选自H、C1-C6烷基、C1-C6卤代烷基和C2-C4炔基;n为选自0、1、2、3、4和5的整数。
2.根据权利要求1的用途,其中在式I中R1选自O和NH并且R2选自CH和N,条件是在R1是NH的情况下R2是N。
3.根据权利要求1或2的用途,其中在式I中R3选自C1-C2烷基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C2烷基。
4.根据权利要求1-3中任一项的用途,其中在式I中R4选自C1-C4烷基、C2-C4链烯基、-C(=O)-C1-C2烷基、C1-C4卤代烷基、C2-C4卤代链烯基和-(C1-C2烷基)-O-(C1-C2烷基)。
5.根据权利要求1-4中任一项的用途,其中在式I中Ra选自C1-C3烷基、C2-C3链烯基、C2-C3炔基、-O-C1-C3烷基、-C(=N-O-C1-C2烷基)-C1-C2烷基、-O-CH2-C(=N-O-C1-C2烷基)-C1-C2烷基、C3-C4环烷基、-C1-C2烷基-C3-C4环烷基、-O-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基和杂芳基直接或者经由氧原子或经由亚甲基连接基键合,并且其中Ra的脂族和环状结构部分未被取代或者带有1、2或3个相互独立地选自卤素、CN、甲基和C1卤代烷基的相同或不同基团Rb。
6.根据权利要求1-5中任一项的用途,其中所述植物病原性真菌是大豆锈病(豆薯层锈菌和/或山马蟥层锈菌)。
7.一种防除在线粒体细胞色素b蛋白中含有赋予对Qo抑制剂的耐受性的氨基酸替代F129L的植物病原性真菌的方法,包括用有效量的至少一种如权利要求1-5中任一项所定义的式I化合物或者包含它的组合物治疗性和/或预防性处理处于因所述植物病原性真菌发生病害危险中的植物或所述植物的植物繁殖材料和/或对所述植物病原性真菌施用有效量的至少一种如权利要求1-5中任一项所定义的式I化合物或者包含它的组合物。
8.式I化合物及其立体异构体和互变异构体形式以及其N-氧化物和可农用盐:
其中
R1选自O和NH;
R2选自CH和N;
R3选自C1-C4烷基、C2-C4链烯基、C1-C2单卤代烷基、C1-C2二卤代烷基、单卤代乙烯基、二卤代乙烯基、C3-C6环烷基和-O-C1-C4烷基;
R4选自C1-C6烷基、C2-C4链烯基、C2-C4炔基、C1-C6卤代烷基、C2-C4卤代链烯基、C2-C4卤代炔基、-C(=O)-C1-C4烷基、-(C1-C2烷基)-O-(C1-C2烷基)、-(C1-C2烷基)-O-(C1-C2卤代烷基)和-C1-C4烷基-C3-C6环烷基;
Ra选自CN、NH-C1-C4烷基、N(C1-C4烷基)2、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C4烷基、-C(=N-O-C1-C4烷基)-C1-C4烷基、C3-C6环烷基、C3-C6环烯基、-C1-C2烷基-C3-C6环烷基、-O-C3-C6环烷基、苯基、3-6员杂环烷基、3-6员杂环烯基和5或6员杂芳基,
其中所述杂环烷基、杂环烯基和杂芳基除了碳原子外含有1、2或3个选自N、O和S的杂原子,
其中所述苯基、杂环烷基、杂环烯基和杂芳基直接或者经由氧原子或经由C1-C2亚烷基连接基键合,
并且其中Ra的脂族和环状结构部分未被取代或者带有1、2、3、4个或至多最大数目的相同或不同基团Rb:
Rb选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基;
n为选自0、1、2、3、4和5的整数。
9.根据权利要求8的化合物,其中R1选自O和NH;并且R2选自CH和N,条件是在R1是NH的情况下R2是N。
10.根据权利要求8或9的化合物,其中R3选自C1-C2烷基、C1-C2单卤代烷基、C1-C2二卤代烷基、C3-C4环烷基和-O-C1-C2烷基。
11.根据权利要求8-10中任一项的化合物,其中R4选自C1-C6烷基、C2-C4链烯基、C1-C6卤代烷基、C2-C4卤代链烯基、-(C1-C2烷基)-O-(C1-C2烷基)和-(C1-C2烷基)-O-(C1-C2卤代烷基)。
12.根据权利要求8-11中任一项的化合物,其中n为1、2或3。
13.根据权利要求8-12中任一项的化合物,其中Ra选自CN、NH-C1-C2烷基、N(C1-C2烷基)2、C1-C4烷基、C2-C4链烯基、C2-C4炔基、-O-C1-C4烷基、-C(=O)-C1-C2烷基、-C=(N-O-CH3)-CH3、C3-C4环烷基、-O-C3-C4环烷基、苯基、3-5员杂环烷基和5或6员杂芳基,其中所述杂环烷基和杂芳基除了碳原子外含有1或2个选自N、O和S的杂原子,其中所述苯基、杂环烷基和杂芳基直接或者经由氧原子或经由亚甲基连接基键合,并且其中所述苯基未被取代或者带有1、2或3个选自CN、NH2、NO2、C1-C4烷基和-O-C1-C4烷基的相同或不同基团Rb。
14.农业化学组合物,包含助剂和至少一种如权利要求8-13中任一项所定义的式I化合物或其立体异构体或可农用盐或互变异构体或N-氧化物形式。
15.一种防除植物病原性真菌的方法,包括用至少一种如权利要求8-13中任一项所定义的式I化合物或者如权利要求14所定义的农业化学组合物治疗性和/或预防性处理处于因所述植物病原性真菌发生病害危险中的植物或所述植物的植物繁殖材料和/或对所述植物病原性真菌施用至少一种如权利要求8-13中任一项所定义的式I化合物或者如权利要求14所定义的农业化学组合物。
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