CN117355519A - 用作杀真菌剂的新型取代吡啶类 - Google Patents
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/14—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及式(I)化合物,其中各变量如说明书和权利要求书中所给那样定义。本发明进一步涉及其用途和组合物。
Description
本发明涉及作为杀真菌剂的新型吡啶化合物及其N-氧化物和盐及其用途。本发明还涉及包含至少一种化合物I的组合物、防除植物病原性真菌的方法以及用至少一种式I化合物涂敷的种子。
WO201018686、WO201347441公开了一些吡啶化合物。然而,在许多情况下,尤其是在低施用率下,已知化合物的杀真菌活性并不令人满意。基于此,本发明的目的是要提供对植物病原性真菌具有改进活性和/或更宽活性谱的化合物。本发明的另一目的是要提供具有改进毒理学性能或改进环境命运性能的杀真菌剂。
这些和其他目的由下面所定义的式(I)的吡啶化合物及其可农用盐实现。
因此,本发明涉及作为杀真菌剂的式I化合物及其N-氧化物和可农用盐:
其中
R1为H;
R2在每种情况下独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、O-C1-C6烷基、C3-C6环烷基;R3在每种情况下独立地选自C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、O-C1-C6烷基、C3-C6环烷基;
R4为H;
R5在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中这些结构部分未被取代或者被1-3个相互独立地选自如下的基团R5a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;
R6在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中R6的这些结构部分未被取代或者被1-3个相互独立地选自如下的基团R6a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;或者
R5和R6与它们所键合的C原子一起形成=O;或者
R5和R6与它们所键合的C原子一起形成C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环,其中该环烷基或杂环可以未被取代或者被卤素、C1-C6烷基、C1-C6卤代烷基取代;
R7在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中这些结构部分未被取代或者被1-3个相互独立地选自如下的基团R7a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;
R8在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中这些结构部分未被取代或者被1-3个相互独立地选自如下的基团R8a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;或者
R7和R8与它们所键合的C原子一起形成C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环;
X在每种情况下独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基、O-C1-C6卤代烷基、C3-C6环烷基、C2-C6链烯基、C2-C6炔基;
n为0、1、2或3,
条件是R5、R6、R7、R8不能全部为H。
N-氧化物可以由本发明化合物根据常规氧化方法制备,例如通过用有机过酸如间氯过苯甲酸(参见WO 03/64572或J.Med.Chem.38(11),1892-903,1995);或用无机氧化剂如过氧化氢(参见J.Heterocyc.Chem.18(7),1305-8,1981)或过硫酸氢钾制剂(参见J.Am.Chem.Soc.123(25),5962-5973,2001)处理化合物I。氧化可能得到纯的单-N-氧化物或不同N-氧化物的混合物,后者可以通过常规方法如层析分离。
式I化合物的可农用盐尤其包括其阳离子和阴离子分别对化合物I的杀真菌作用没有不利影响的那些阳离子的盐或那些酸的酸加成盐。合适的阳离子因此尤其是碱金属离子,优选钠和钾的离子,碱土金属离子,优选钙、镁和钡的离子,过渡金属离子,优选锰、铜、锌和铁的离子,还有需要的话可以被1-4个C1-C4烷基取代基和/或一个苯基或苄基取代基取代的铵离子,优选二异丙基铵、四甲基铵、四丁基铵、三甲基苄基铵,此外还有离子,锍离子,优选三(C1-C4烷基)锍,以及氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可以通过使化合物I与相应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式I化合物可以作为一种或多种立体异构体存在。各种立体异构体包括对映体、非对映体、由绕不对称基团的单键旋转受限而出现的阻转异构体和几何异构体。它们也形成本发明主题的一部分。本领域熟练技术人员应理解一种立体异构体在富集时相对于其他立体异构体或者在与其他立体异构体分离时可能更具活性和/或可能呈现有益效果。额外地,熟练技术人员知道如何分离、富集和/或选择性制备所述立体异构体。本发明化合物可以作为立体异构体的混合物,例如外消旋体,单独的立体异构体,或者作为光学活性形式存在。
式I化合物可以以其生物学活性可能不同的不同晶型存在。它们也形成本发明主题的一部分。
就各变量而言,在化合物I的制备过程中得到的中间体的实施方案对应于式I化合物的实施方案。术语“化合物I”是指式I化合物。
在下文中进一步描述中间体化合物。熟练技术人员容易理解本文就化合物I所给取代基的优选情形,尤其还有在下表中对相应取代基所给那些,相应地适用于中间体。因此,取代基在每种情况下相互独立地或者更优选组合地具有本文所定义的含义。
若合成得到异构体混合物,则通常不一定要求分离,因为在某些情况下各异构体可能在为了应用的后处理过程中或在施用过程中(例如在光、酸或碱的作用下)相互转化。该类转化也可以在使用后发生,例如在植物处理的情况下在被处理的植物中或在待防治的有害真菌中。
在上面所给变量的定义中,使用通常为所述取代基的代表的集合性术语。术语“Cn-Cm”表示每种情况下在所述取代基或取代基结构部分中可能的碳原子数。
术语“卤素”涉及氟、氯、溴和碘。
术语“C1-C6烷基”涉及具有1-6个碳原子的直链或支化饱和烃基,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。同样,术语“C2-C4烷基”涉及具有2-4个碳原子的直链或支化烷基,如乙基、丙基(正丙基)、1-甲基乙基(异丙基)、丁基、1-甲基丙基(仲丁基)、2-甲基丙基(异丁基)、1,1-二甲基乙基(叔丁基)。
术语“C1-C6卤代烷基”涉及如上所定义的具有1或6个碳原子的烷基,其中这些基团中的部分或所有氢原子可以被如上所述的卤原子替代。实例是“C1-C2卤代烷基”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、2,2,2-三氯乙基或五氟乙基。
术语“C1-C6烷氧基”涉及经由氧在烷基中的任意位置键合的具有1-6个碳原子的直链或支化烷基。实例是“C1-C4烷氧基”,如甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基。
术语“C1-C6卤代烷氧基”涉及如上所定义的C1-C6烷氧基,其中在这些基团中的部分或所有氢原子可以被如上所述的卤原子替代。实例是“C1-C4卤代烷氧基”,如OCH2F、OCHF2、OCF3、OCH2Cl、OCHCl2、OCCl3、氯氟甲氧基、二氯一氟甲氧基、一氯二氟甲氧基、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、OC2F5、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、OCH2-C2F5、OCF2-C2F5、1-氟甲基-2-氟乙氧基、1-氯甲基-2-氯乙氧基、1-溴甲基-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基。
术语“C2-C6链烯基”涉及具有2-6个碳原子和在任意位置的双键的直链或支化不饱和烃基。实例是“C2-C4链烯基”,如乙烯基、1-丙烯基、2-丙烯基(烯丙基)、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-C6卤代链烯基”涉及如上所定义的具有2或6个碳原子的烷基,其中在这些基团中的部分或所有氢原子可以被如上所述的卤原子替代。
术语“C2-C6链烯氧基”涉及经由氧在链烯基中的任意位置键合的具有2-6个碳原子的直链或支化链烯基。实例是“C2-C4链烯氧基”。
术语“C2-C6炔基”涉及具有2-6个碳原子且含有至少一个叁键的直链或支化不饱和烃基。实例是“C2-C4炔基”,如乙炔基、丙-1-炔基、丙-2-炔基(炔丙基)、丁-1-炔基、丁-2-炔基、丁-3-炔基、1-甲基丙-2-炔基。
术语“C2-C6卤代炔基”涉及如上所定义的具有2或6个碳原子的烷基,其中在这些基团中的部分或所有氢原子可以被如上所述的卤原子替代。
术语“C2-C6炔氧基”涉及经由氧在炔基中的任意位置键合的具有2-6个碳原子的直链或支化炔基。实例是“C2-C4炔氧基”。
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、环丁基、环戊基、环己基。因此,3、4、5、6、7、8、9或10员饱和碳环基或碳环是“C3-C10环烷基”。
术语“C3-C6环烯基”涉及具有3-6个碳环成员和至少一个双键的3、4、5或6员单环部分不饱和碳环,如环戊烯基、环戊二烯基、环己二烯基。因此,3、4、5、6、7、8、9或10员部分不饱和碳环基或碳环是“C3-C10环烯基”。
术语“C3-C8环烷基-C1-C4烷基”涉及具有1-4个碳原子的烷基(如上所定义),其中烷基的一个氢原子被具有3-8个碳原子的环烷基(如上所定义)替代。
术语“3、4、5、6、7、8、9或10员饱和或部分不饱和杂环基或杂环,其中该杂环基或杂环含有1、2、3或4个选自N、O和S的杂原子”应理解为指饱和和部分不饱和杂环二者,其中该杂环的环成员原子除了碳原子外包括1、2、3或4个独立地选自O、N和S的杂原子。例如:
含有1或2个选自O、N和S的杂原子作为环成员的3或4员饱和杂环,如环氧乙烷、氮丙啶、硫杂丙环、氧杂环丁烷、氮杂环丁烷、硫杂环丁烷、[1,2]二氧杂环丁烷、[1,2]二硫杂环丁烷、[1,2]二氮杂环丁烷;以及
含有1、2或3个选自O、N和S的杂原子作为环成员的5或6员饱和或部分不饱和杂环,如2-四氢呋喃基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、2-吡咯烷基、3-吡咯烷基、3-异唑烷基、4-异/>唑烷基、5-异/>唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-/>唑烷基、4-/>唑烷基、5-/>唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、2-咪唑烷基、4-咪唑烷基、1,2,4-/>二唑烷-3-基、1,2,4-/>二唑烷-5-基、1,2,4-噻二唑烷-3-基、1,2,4-噻二唑烷-5-基、1,2,4-三唑烷-3-基、1,3,4-/>二唑烷-2-基、1,3,4-噻二唑烷-2-基、1,3,4-三唑烷-2-基、2,3-二氢呋喃-2-基、2,3-二氢呋喃-3-基、2,4-二氢呋喃-2-基、2,4-二氢呋喃-3-基、2,3-二氢噻吩-2-基、2,3-二氢噻吩-3-基、2,4-二氢噻吩-2-基、2,4-二氢噻吩-3-基、2-吡咯啉-2-基、2-吡咯啉-3-基、3-吡咯啉-2-基、3-吡咯啉-3-基、2-异/>唑啉-3-基、3-异/>唑啉-3-基、4-异/>唑啉-3-基、2-异/>唑啉-4-基、3-异/>唑啉-4-基、4-异/>唑啉-4-基、2-异/>唑啉-5-基、3-异唑啉-5-基、4-异/>唑啉-5-基、2-异噻唑啉-3-基、3-异噻唑啉-3-基、4-异噻唑啉-3-基、2-异噻唑啉-4-基、3-异噻唑啉-4-基、4-异噻唑啉-4-基、2-异噻唑啉-5-基、3-异噻唑啉-5-基、4-异噻唑啉-5-基、2,3-二氢吡唑-1-基、2,3-二氢吡唑-2-基、2,3-二氢吡唑-3-基、2,3-二氢吡唑-4-基、2,3-二氢吡唑-5-基、3,4-二氢吡唑-1-基、3,4-二氢吡唑-3-基、3,4-二氢吡唑-4-基、3,4-二氢吡唑-5-基、4,5-二氢吡唑-1-基、4,5-二氢吡唑-3-基、4,5-二氢吡唑-4-基、4,5-二氢吡唑-5-基、2,3-二氢/>唑-2-基、2,3-二氢/>唑-3-基、2,3-二氢唑-4-基、2,3-二氢/>唑-5-基、3,4-二氢/>唑-2-基、3,4-二氢/>唑-3-基、3,4-二氢唑-4-基、3,4-二氢/>唑-5-基、3,4-二氢/>唑-2-基、3,4-二氢/>唑-3-基、3,4-二氢唑-4-基、2-哌啶基、3-哌啶基、4-哌啶基、1,3-二/>烷-5-基、2-四氢吡喃基、4-四氢吡喃基、2-四氢噻吩基、3-六氢哒嗪基、4-六氢哒嗪基、2-六氢嘧啶基、4-六氢嘧啶基、5-六氢嘧啶基、2-哌嗪基、1,3,5-六氢三嗪-2-基和1,2,4-六氢三嗪-3-基以及还有相应的-亚基;以及7员饱和或部分不饱和杂环如四氢-和六氢氮杂/>基,如2,3,4,5-四氢[1H]氮杂/>-1-、-2-、-3-、-4-、-5-、-6-或-7-基,3,4,5,6-四氢[2H]氮杂/>-2-、-3-、-4-、-5-、-6-或-7-基,2,3,4,7-四氢[1H]氮杂/>-1-、-2-、-3-、-4-、-5-、-6-或-7-基,2,3,6,7-四氢[1H]氮杂-1-、-2-、-3-、-4-、-5-、-6-或-7-基,六氢氮杂/>-1-、-2-、-3-或-4-基,四氢-和六氢氧杂环庚三烯基(oxepinyl)如2,3,4,5-四氢[1H]氧杂环庚三烯-2-、-3-、-4-、-5-、-6-或-7-基,2,3,4,7-四氢[1H]氧杂环庚三烯-2-、-3-、-4-、-5-、-6-或-7-基,2,3,6,7-四氢[1H]氧杂环庚三烯-2-、-3-、-4-、-5-、-6-或-7-基,六氢氮杂/>-1-、-2-、-3-或-4-基,四氢-和六氢-1,3-二氮杂/>基,四氢-和六氢-1,4-二氮杂/>基,四氢-和六氢-1,3-氧氮杂/>基(oxazepinyl),四氢-和六氢-1,4-氧氮杂/>基,四氢-和六氢-1,3-二氧杂环庚三烯基(dioxepinyl),四氢-和六氢-1,4-二氧杂环庚三烯基以及相应的-亚基。
术语“取代的”涉及被1、2、3个或至多最大可能数目的取代基取代。
术语“5或6员杂芳基”或“5或6员杂芳族”涉及除了碳原子外包括1、2、3或4个独立地选自N、O和S的杂原子的芳族环体系,例如5员杂芳基如吡咯-1-基、吡咯-2-基、吡咯-3-基、噻吩-2-基、噻吩-3-基、呋喃-2-基、呋喃-3-基、吡唑-1-基、吡唑-3-基、吡唑-4-基、吡唑-5-基、咪唑-1-基、咪唑-2-基、咪唑-4-基、咪唑-5-基、唑-2-基、/>唑-4-基、/>唑-5-基、异/>唑-3-基、异/>唑-4-基、异/>唑-5-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、1,2,4-三唑-1-基、1,2,4-三唑-3-基、1,2,4-三唑-5-基、1,2,4-/>二唑-3-基、1,2,4-/>二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基;或者6员杂芳基,如吡啶-2-基、吡啶-3-基、吡啶-4-基、哒嗪-3-基、哒嗪-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、吡嗪-2-基、1,3,5-三嗪-2-基和1,2,4-三嗪-3-基。
在下文中描述本发明化合物的特殊实施方案。在本文中进一步详述相应取代基的具体含义,其中这些含义在每种情况下单独但也以相互间的任意组合为本发明的特殊实施方案。
此外,就各变量而言,化合物I的实施方案通常还适用于中间体。
根据式I化合物的一个实施方案,R1为H。
根据式I化合物的一个实施方案,R2选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、O-C1-C6烷基、C3-C6环烷基。
根据式I化合物的另一实施方案,R2为卤素,尤其是F、Cl、Br或I,更具体而言F、Cl或Br,尤其是F或Cl。
根据式I化合物的另一实施方案,R2为F。
根据式I化合物的另一实施方案,R2为Cl。
根据式I化合物的另一实施方案,R2为Br。
根据式I化合物的另一实施方案,R2为CN。
根据式I化合物的另一实施方案,R2为C1-C6烷基,尤其是C1-C4烷基,如CH3或C2H5,尤其是CH3或CH2CH3。
根据式I化合物的另一实施方案,R2为C1-C6卤代烷基,尤其是C1-C4卤代烷基,如CF3。
根据式I化合物的再一实施方案,R2为C2-C6链烯基,尤其是C2-C4链烯基,如CH=CH2、C(CH3)=CH2、CH2CH=CH2。
根据式I化合物的另一具体实施方案,R2为O-C1-C6烷基,尤其是C1-C4烷基,更具体为C1-C2烷氧基。R2为如OCH3或OCH2CH3。
根据式I化合物的另一实施方案,R2为C3-C6环烷基,尤其是环丙基或环丁基。
R2的特别优选实施方案根据本发明在下表P2中,其中第P2-1至P2-19行的各行对应于本发明的一个特定实施方案,其中P2-1至P2-19也以相互间的任意组合为本发明的优选实施方案。与R2所键合的碳原子的连接点在图中标有“#”。
表P2:
根据式I的一个实施方案,R3选自C1-C6烷基、C1-C6卤代烷基,尤其是CH3、C2H5、CF3、CH2F、CHF2,更具体为CH3、CH2F、CF2H、CF3、环丙基、环丁基,最优选CH3、CF3、CF2H。
根据式I化合物的另一实施方案,R3为C1-C6烷基,尤其是C1-C4烷基,如CH3或C2H5,尤其是CH3或CH2CH3。
根据式I化合物的另一实施方案,R3为C1-C6卤代烷基,尤其是C1-C4卤代烷基,如CF3、FCH2、F2CH、CF3CH2。
根据式I化合物的再一实施方案,R3为C2-C6链烯基,尤其是C2-C4链烯基,如CH=CH2、C(CH3)=CH2、CH2CH=CH2。
根据式I化合物的另一具体实施方案,R3为O-C1-C6烷基,尤其是C1-C4烷基,更具体为C1-C2烷氧基。R3为如OCH3或OCH2CH3。
根据式I化合物的另一实施方案,R3为C3-C6环烷基,尤其是环丙基、环丁基。
R3的特别优选实施方案根据本发明在下表P3中,其中第P3-1至P3-15行的各行对应于本发明的一个特定实施方案,其中P3-1至P3-15也以相互间的任意组合为本发明的优选实施方案。与R3所键合的碳原子的连接点在图中标有“#”。
表P3:
根据式I化合物的一个实施方案,R4为H。
根据式I化合物的一个实施方案,R5在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中它们未被取代或者被1-3个相互独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基的基团R5a取代。
根据式I化合物的一个实施方案,R5在每种情况下独立地选自C1-C6烷基(实施方案5.1)、C1-C6卤代烷基(实施方案5.2)、H(实施方案5.3)、苯基、CH2-苯基(实施方案5.4),其中苯基和CH2-苯基未被取代或者被一个或两个卤素取代。
根据式I化合物的另一实施方案,R5为CH3或CF3。
根据式I化合物的另一实施方案,R5为CH3。
根据式I化合物的另一实施方案,R5为H。
根据式I化合物的另一实施方案,R5为H、CH2CH3、CH(CH3)2、CH(CH3)CH2CH3、C(CH3)3、CH2-CH(CH3)2、CH2-C(CH3)3。
根据式I化合物的另一实施方案,R5为苯基、2-F-苯基、4-F-苯基、2,4-F2-苯基、2-Cl-苯基、4-Cl-苯基、CH2-苯基、CH2-2-F-苯基、CH2-4-F-苯基。
根据式I化合物的一个实施方案,R6在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中这些结构部分未被取代或者被1-3个相互独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基的基团R6a取代。
根据式I化合物的一个实施方案,R6在每种情况下独立地选自C1-C6烷基(实施方案6.1)、H(实施方案6.2)。
根据式I化合物的另一实施方案,R6为H、CH3、CH2CH3、CH(CH3)2、CH(CH3)CH2CH3、C(CH3)3、CH2-CH(CH3)2、CH2-C(CH3)3、CH2-CH(CH3)-C(CH3)3、CH2-CH2-C(CH3)3。
根据式I化合物的另一实施方案,R5和R6与它们所键合的C原子一起形成=O或者C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环,其中该环烷基或杂环可以未被取代或者被卤素、C1-C6烷基、C1-C6卤代烷基取代。
根据式I化合物的另一实施方案,R5和R6形成=O(实施方案6.3)。
根据式I化合物的另一实施方案,R5和R6形成C3-C6环烷基(实施方案6.4)。
根据式I化合物的另一实施方案,R5和R6形成含有1、2或3个选自O和S的杂原子的3-6员饱和杂环。
根据式I化合物的另一实施方案,R5和R6形成含有一个O的3-6员饱和杂环(实施方案6.5)。
R5、R6的优选实施方案根据本发明在下表P5中,其中第P5-1至P5-19行的各行对应于本发明的一个特定实施方案,其中P5-1至P5-19也以相互间的任意组合为本发明的优选实施方案。与R5和R6所键合的碳原子的连接点在图中标有“#”。
表P5,6:
根据式I化合物的一个实施方案,R7在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C1-C6烷基-O-C1-C6烷基、苯基、苄基,其中这些结构部分未被取代或者被1-3个相互独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基的基团R7a取代。
根据式I化合物的一个实施方案,R7在每种情况下独立地选自C1-C6烷基(实施方案7.1)、C1-C6卤代烷基(实施方案7.2)、C1-C6烷基-O-C1-C6烷基(实施方案7.3)、苯基、CH2-苯基(实施方案7.4),其中苯基和CH2-苯基未被取代或者被一个或两个卤素取代。
根据式I化合物的另一实施方案,R7为CH3或CF3。
根据式I化合物的另一实施方案,R7为CH3。
根据式I化合物的另一实施方案,R7为H。
根据式I化合物的另一实施方案,R7为CH2CH3、CH(CH3)2、CH(CH3)CH2CH3、C(CH3)3、CH2-CH(CH3)2、CH2-C(CH3)3、CH2-O-CH3。
根据式I化合物的另一实施方案,R7为苯基、2-F-苯基、4-F-苯基、2,4-F2-苯基、2-Cl-苯基、4-Cl-苯基、CH2-苯基、CH2-2-F-苯基、CH2-4-F-苯基。
根据式I化合物的一个实施方案,R8在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C1-C6烷基-O-C1-C6烷基、苯基、苄基、C1-C6烷基-O-苯基,其中这些结构部分未被取代或者被1-3个相互独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基的基团R6a取代。
根据式I化合物的一个实施方案,R8在每种情况下独立地选自C1-C6烷基(实施方案8.1)、C1-C6烷基-O-苯基(实施方案8.2)、C1-C6烷基-O-C1-C6烷基(实施方案8.3)。
根据式I化合物的另一实施方案,R8为CH2CH3、CH(CH3)2、CH(CH3)CH2CH3、C(CH3)3、CH2-CH(CH3)2、CH2-C(CH3)3、CH2-CH(CH3)-C(CH3)3、CH2-CH2-C(CH3)3、CH2-O-CH3、CH2-O-(CH3)3、CH2-O-苯基。
根据式I化合物的另一实施方案,R7和R8与它们所键合的C原子一起形成C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环。
根据式I化合物的另一实施方案,R7和R8形成C3-C6环烷基(实施方案8.4)。
根据式I化合物的另一实施方案,R7和R8形成含有1、2或3个选自O和S的杂原子的3-6员饱和杂环。
根据式I化合物的另一实施方案,R7和R8形成含有一个O的3-6员饱和杂环(实施方案8.5)。
R7和R8的优选实施方案根据本发明在下表P5中,其中第P5-1至P5-18行的各行对应于本发明的一个特定实施方案,其中P5-1至P5-18也以相互间的任意组合为本发明的优选实施方案。与R5和R6所键合的碳原子的连接点在图中标有“#”。
表P7,8:
根据式I化合物的一个实施方案,X在每种情况下独立地选自卤素(实施方案X.1)、CN、C1-C6烷基(实施方案X.2)、C1-C6卤代烷基(实施方案X.3)、O-C1-C6烷基(实施方案X.4)、O-C1-C6卤代烷基(实施方案X.5)。
根据式I化合物的一个实施方案,X在每种情况下独立地选自卤素、O-C1-C6烷基。
根据式I化合物的一个实施方案,X在每种情况下独立地选自F或Cl。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X为F。
根据一个实施方案,Xn如下所定义:
并且X选自F、Cl、I、CH3、环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据一个实施方案,Xn如下所定义:
并且X为F。
根据一个实施方案,Xn如下所定义:
并且X为H。
根据一个实施方案,Xn如下所定义:
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并且X选自F、Cl、I、CH3、 环丙基、CH=CH2、C≡CH、OCH3、OCHF2、CF3、CHF2、CH2CH3、CN。
根据式I化合物的一个实施方案,n为0。
根据式I化合物的一个实施方案,n为1。
根据式I化合物的一个实施方案,n为2。
式I化合物包含一个或多个手性中心并且通常以外消旋体形式得到。R-和S-对映体可以用熟练技术人员已知的方法,例如通过使用手性HPLC而以纯净形式分离和离析。
因此,根据本发明,式I化合物可以以下列形式使用:
-(R)-对映体和(S)-对映体的外消旋混合物;
-任意其他比例的(R)-对映体和(S)-对映体的混合物;
-纯(R)-对映体,或者
-纯(S)-对映体。
根据本发明的特定实施方案,式I化合物以(R)-对映体和(S)-对映体的外消旋组合物存在,但(R)-对映体和(S)-对映体还可以以任意其他比例存在,例如式I化合物的纯对映体(R)或纯对映体(S)。
根据一个具体实施方案,式I化合物作为对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,仍更优选至少98%,最优选至少99%的(R)-对映体提供和使用。
根据另一具体实施方案,式I化合物作为对映体过量(e.e.)为至少40%,例如至少50%、60%、70%或80%,优选至少90%,更优选至少95%,仍更优选至少98%,最优选至少99%的(S)-对映体提供和使用。
本发明在其他方面涉及表E所列实施方案E.1-E.275,其代表上面对变量R2、R3和X(由实施方案X.1-X.6表示)各自所定义的实施方案的优选组合,式I化合物中的n如下所定义。
表E:
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本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.1表示且R6由实施方案6.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.2表示且R6由实施方案6.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.3表示且R6由实施方案6.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.4表示且R6由实施方案6.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.1表示且R6由实施方案6.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.2表示且R6由实施方案6.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.3表示且R6由实施方案6.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.4表示且R6由实施方案6.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.1表示且R6由实施方案6.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.2表示且R6由实施方案6.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.3表示且R6由实施方案6.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5由实施方案5.4表示且R6由实施方案6.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5和R6由实施方案6.4表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R5和R6由实施方案6.5表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R7由实施方案7.1表示且R8由实施方案8.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R7由实施方案7.2表示且R8由实施方案8.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R7由实施方案7.3表示且R8由实施方案8.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R7由实施方案7.4表示且R8由实施方案8.1表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.275,其中R7由实施方案7.1表示且R8由实施方案8.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.2表示且R8由实施方案8.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.3表示且R8由实施方案8.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.4表示且R8由实施方案8.2表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.1表示且R8由实施方案8.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.2表示且R8由实施方案8.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.3表示且R8由实施方案8.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7由实施方案7.4表示且R8由实施方案8.3表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7和R8由实施方案8.4表示。
本发明在其他方面涉及表E中所列实施方案E.1-E.277,其中R7和R8由实施方案8.7表示。
本发明的优选实施方案是下列化合物I.A-1、I.A-2、I.A-3、I.A-4。在这些式中,取代基R5、R6、R7和R8以及Xn独立地如上所定义或者优选如本文所定义:
尤其考虑到它们的用途,根据一个实施方案优选汇编在表1a-7a中的式I.A-1、I.A-2、I.A-3、I.A-4化合物。此外,对表中取代基所提到的各基团本身为所述取代基的特别优选方面,与其中提到它的组合无关。
表1a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为H且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.1a.B-1至I.A-1.1a.B-25、I.A-2.1a.B-1至I.A-2.1a.B-25、I.A-3.1a.B-1至I.A-3.1a.B-25、I.A-4.1a.B-1至I.A-4.1a.B-25)。
表2a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为8-F且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.2a.B-1至I.A-1.2a.B-25、I.A-2.2a.B-1至I.A-2.2a.B-25、I.A-3.2a.B-1至I.A-3.2a.B-25、I.A-4.2a.B-1至I.A-4.2a.B-25)。
表3a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为8-Cl且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.3a.B-1至I.A-1.3a.B-25、I.A-2.3a.B-1至I.A-2.3a.B-25、I.A-3.3a.B-1至I.A-3.3a.B-25、I.A-4.3a.B-1至I.A-4.3a.B-25)。
表4a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为7,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.4a.B-1至I.A-1.4a.B-25、I.A-2.4a.B-1至I.A-2.4a.B-25、I.A-3.4a.B-1至I.A-3.4a.B-25、I.A-4.4a.B-1至I.A-4.4a.B-25)。
表5a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为5,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.5a.B-1至I.A-1.5a.B-25、I.A-2.5a.B-1至I.A-2.5a.B-25、I.A-3.5a.B-1至I.A-3.5a.B-25、I.A-4.5a.B-1至I.A-4.5a.B-25)。
表6a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为7-OCH3且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.6a.B-1至I.A-1.6a.B-25、I.A-2.6a.B-1至I.A-2.6a.B-25、I.A-3.6a.B-1至I.A-3.6a.B-25、I.A-4.6a.B-1至I.A-4.6a.B-25)。
表7a式I.A-1、I.A-2、I.A-3、I.A-4化合物,其中Xn为6,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.A-1.7a.B-1至I.A-1.7a.B-25、I.A-2.7a.B-1至I.A-2.7a.B-25、I.A-3.7a.B-1至I.A-3.7a.B-25、I.A-4.7a.B-1至I.A-5.7a.B-25)。
本发明的优选实施方案是下列化合物I.B-1、I.B-2、I.B-3、I.B-4。在这些式中,取代基R5、R6、R7和R8以及Xn独立地如上所定义或者优选如本文所定义:
尤其考虑到它们的用途,根据一个实施方案优选汇编在表1b-7b中的式I.B-1、I.B-2、I.B-3、I.B-4化合物。此外,对表中取代基所提到的各基团本身为所述取代基的特别优选方面,与其中提到它的组合无关。
表1b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为H且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.1b.B-1至I.B-1.1b.B-25、I.B-2.1b.B-1至I.B-2.1b.B-25、I.B-3.1b.B-1至I.B-3.1b.B-25、I.B-4.1b.B-1至I.B-4.1b.B-25)。
表2b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为8-F且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.2b.B-1至I.B-1.2b.B-25、I.B-2.2b.B-1至I.B-2.2b.B-25、I.B-3.2b.B-1至I.B-3.2b.B-25、I.B-4.2b.B-1至I.B-4.2b.B-25)。
表3b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为8-Cl且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.3b.B-1至I.B-1.3b.B-25、I.B-2.3b.B-1至I.B-2.3b.B-25、I.B-3.3b.B-1至I.B-3.3b.B-25、I.B-4.3b.B-1至I.B-4.3b.B-25)。
表4b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为7,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.4b.B-1至I.B-1.4b.B-25、I.B-2.4b.B-1至I.B-2.4b.B-25、I.B-3.4b.B-1至I.B-3.4b.B-25、I.B-4.4b.B-1至I.B-4.4b.B-25)。
表5b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为5,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.5b.B-1至I.B-1.5b.B-25、I.B-2.5b.B-1至I.B-2.5b.B-25、I.B-3.5b.B-1至I.B-3.5b.B-25、I.B-4.5b.B-1至I.B-4.5b.B-25)。
表6b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为7-OCH3且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.6b.B-1至I.B-1.6b.B-25、I.B-2.6b.B-1至I.B-2.6b.B-25、I.B-3.6b.B-1至I.B-3.6b.B-25、I.B-4.6b.B-1至I.B-4.6b.B-25)。
表7b式I.B-1、I.B-2、I.B-3、I.B-4化合物,其中Xn为6,8-F2且R5和R6的组合的含义对各单独化合物而言在每种情况下对应于表B的一行(化合物I.B-1.7b.B-1至I.B-1.7b.B-25、I.B-2.7b.B-1至I.B-2.7b.B-25、I.B-3.7b.B-1至I.B-3.7b.B-25、I.B-4.7b.B-1至I.B-5.7b.B-25)。
表B
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本发明化合物可以如下面的方案所示制备,其中除非另有说明,各变量的定义如上面对式I化合物所定义。式I化合物可以根据现有技术中所述方法或者类似于现有技术中所述方法制备。该合成利用可市购或者可以根据常规程序由易得化合物制备的原料。
例如,化合物I可以通过在有机溶剂中式(2)所示有机硼酸衍生物和式(6)所示亚氨基卤(imidoyl halide)衍生物之间使用钯配合物的钯催化Suzuki偶联反应制备。优选如WO2009119089A1所述在升高的温度,优选60-160℃下使用1-3当量式3所示有机硼酸衍生物/1当量亚氨基卤衍生物(6)进行该反应。
式(6)所示亚氨基化合物可以如US 2011/0136782 A1所述通过一种其中在合适的卤化剂如三苯基膦和四卤化碳、二氯三苯基膦、光气、草酰氯或亚硫酰氯存在下使式(7)所示环状酰胺反应的方法制备。
式(7)所示化合物可以通过由Schmidt反应将式(9)所示环状苯乙酮衍生物衍生为肟并随后进行Beckmann重排而制备。对这两种反应已经报道了各种变化。Schmidt反应可以通过例如使酮在叠氮化钠和强酸,如浓盐酸、硫酸、三氟乙酸或甲磺酸中在不存在溶剂下或者在溶剂如乙腈、氯仿或二氯甲烷中反应而进行。在Beckmann重排中,使羰基化合物的肟与聚磷酸或其三甲基甲硅烷基酯反应,或者在高温下与路易斯酸如三碘化铝或氯化铁(III)浸渍的蒙脱石或与亚硫酰氯在不存在溶剂下或者在溶剂如乙腈存在下反应。此外,它还可以如Heterocycles(1994),38(2),305-18;US 2011/0136782 A1所述通过形成肟的甲磺酸酯或甲苯磺酸酯,然后用碱如氢氧化钠水溶液处理或用路易斯酸如二乙基氯化铝处理而制备。
替换地,式(7)所示化合物可以如Synthesis 2019,51(19),3709-3714所述通过酮(9)在温和反应条件下使用羟胺-O-磺酸作为胺化剂的铜(II)催化Beckmann重排而以一锅法制备。
肟(8)可以如Bioorganic&Medicinal Chemistry(2008),16(11),6124-6130;Heterocyclic Communications(1998),4(6),547-557所述通过与盐酸羟胺在溶剂如乙醇中反应,然后必要的话在至多该溶剂的沸点的温度下加入碱如吡啶或乙酸钠或氢氧化钠水溶液而使用已知方法制备。
式(9)所示环状苯乙酮衍生物可市购或者可以如Bioorganic&MedicinalChemistry(2008),16(11),6124-6130;Journal of the Chemical Society,PerkinTransactions 1:Organic and Bio-Organic Chemistry(1995)所述由2-羟基苯乙酮开始经由使用相应酮在吡咯烷存在下的经典闭环反应而得到。
本发明进一步涉及一种制备式I化合物的方法,包括使式Y化合物反应:
其中R5、R6、R7、R8和Xn如上所定义。
本发明进一步涉及式Y化合物:
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其中
R5选自H、C1-C6烷基,
R6选自H、C1-C6烷基,或者
R5和R6与它们所键合的C原子一起形成C3-C6环烷基;
R7选自H、C1-C6烷基,
R8选自H、C1-C6烷基,或者
R7和R8与它们所键合的C原子一起形成C3-C6环烷基;
X为卤素、C1-C6烷基,
n为0、1或2。
根据一个实施方案,
R5选自H、CH3,
R6选自H、CH3,或者
R5和R6与它们所键合的C原子一起形成环丙基;
R7选自H、CH3,
R8选自H、CH3,或者
R7和R8与它们所键合的C原子一起形成环丙基;
X为Cl、F或CH3,
n为0、1或2。
根据另一实施方案,最优选下列化合物Y:
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化合物I及其组合物分别适合作为有效对抗宽范围的植物病原性真菌的杀真菌剂,所述真菌包括土传真菌,特别是选自如下种类: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(Fungiimperfecti))。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,例如糖用甜菜或饲料甜菜;水果,例如仁果(苹果、梨等),核果(例如李、桃、杏仁、樱桃)或也称为浆果的无核小果(草莓、悬钩子、黑莓、鹅莓等);豆科植物,例如扁豆、豌豆、苜蓿或大豆;油料植物,例如油菜、芥菜、橄榄、向日葵、椰子、可可豆、蓖麻油植物、油棕、花生或大豆;葫芦科植物,例如笋瓜、黄瓜或甜瓜;纤维植物,例如棉花、亚麻、大麻或黄麻;柑桔类水果,例如橙子、柠檬、葡萄柚或橘;蔬菜,例如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、西红柿、土豆、葫芦或柿子椒;月桂类植物,例如鳄梨、肉桂或樟脑;能量和原料植物,例如玉米、大豆、油菜、甘蔗或油棕;玉米;烟草;坚果;咖啡;茶;香蕉;葡萄藤(食用葡萄和酿酒用葡萄);啤酒花;草坪;甜叶菊(也称甜菊(Stevia));天然橡胶植物;或观赏和森林植物,例如花卉、灌木、阔叶树或常绿树(针叶树、桉树等);植物繁殖材料如种子和这些植物的作物材料上防治植物病原性真菌。
更优选将化合物I及其组合物分别用于在大田作物,例如土豆、糖用甜菜、烟草、小麦、黑麦、大麦、燕麦、稻、玉米、棉花、大豆、油菜、豆科植物、向日葵、咖啡或甘蔗;水果;葡萄藤;观赏植物;或蔬菜如黄瓜、西红柿、菜豆或笋瓜上防治真菌。
术语“植物繁殖材料”应理解为表示植物的所有有性部分如种子,以及可以用于繁殖植物的无性植物材料如插条和块茎(例如土豆)。这包括种子、根、果实、块茎、球茎、地下茎、枝、芽和其他植物部分,包括在萌发后或出苗后由土壤移植的秧苗和幼苗。
优选分别将化合物I及其组合物对植物繁殖材料的处理用于在禾谷类如小麦、黑麦、大麦和燕麦;稻、玉米、棉花和大豆上防治真菌。
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物种、亚种、变种、品种和/或杂种,包括但不限于冬春季品种,尤其是在禾谷类如小麦和大麦中,以及油菜,例如冬小麦、春小麦、冬大麦等。
玉米也称为印度玉米或玉蜀黍(夏玉米(Zea mays)),包括所有种类的玉米如大田玉米和甜玉米。根据本发明包括所有玉蜀黍或玉米亚种和/或品种,尤其是粉质玉米(Zeamays var.amylacea),爆米花(Zea mays var.everta),顶陷玉米(Zea maysvar.indentata),硬质玉米(Zea mays var.indurata),甜玉米(Zea mays var.saccharata和Zea mays var.rugosa),糯玉米(Zea mays var.ceratina),淀粉玉米(高直链淀粉玉米品种),荚玉米或野生玉米(Zea mays var.tunicata)和七彩玉米(Zea maysvar.japonica)。
大多数大豆栽培种可以分类为无限和有限生长习性,而野大豆(Glycine soja)—大豆的野生祖代—是无限的(PNAS2010,107(19)8563-856)。无限生长习性(成熟期组,MG00至MG 4.9)的特征在于在开始开花之后无性生长的延续,而有限大豆品种(MG 5至MG 8)典型地在开始开花时完成了其无性生长的大部分。根据本发明包括所有大豆栽培种或品种,尤其是无限和有限栽培种或品种。
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。诱变包括使用X射线或致突变化学品的随机诱变,但还有靶向诱变,以在植物基因组的特定座位产生突变。靶向诱变通常使用寡核苷酸或蛋白质如CRISPR/Cas、锌指核酸酶、TALEN或大范围核酸酶。基因工程通常使用重组DNA技术在植物基因组中产生在自然条件下不易通过杂交、诱变或自然重组得到的修饰。通常将一个或多个基因整合到植物的基因组中以添加性状或改善或修饰性状。这些整合的基因也称为转基因,而包含该类转基因的植物被称为转基因植物。该植物转化方法通常产生几个转化事件,它们在其中已经整合了转基因的基因组座上不同。在特定基因组座上包含特定转基因的植物通常被描述为包含特定“事件”,后者由特定事件名称提到。已经引入植物中或者已经修饰的性状包括除草剂耐受性、昆虫抗性、提高的产量以及对非生物条件,如干旱的耐受性。
除草剂耐受性已经通过使用诱变和基因工程产生。已经通过诱变和育种赋予对乙酰乳酸合成酶(ALS)抑制剂除草剂的耐受性的植物例如以名称得到。已经经由使用转基因对草甘膦(glyphosate)、草铵膦(glufosinate)、2,4-D、麦草畏(dicamba)、oxynil除草剂如溴苯腈(bromoxynil)和碘苯腈(ioxynil)、磺酰脲除草剂、ALS抑制剂以及4-羟基苯基丙酮酸二加氧酶(HPPD)抑制剂如异/>氟草(isoxaflutole)和甲基磺草酮(mesotrione)产生除草剂耐受性。
提供除草剂耐受性性状的转基因包括:对于草甘膦耐受性:cp4 epsps、epspsgrg23ace5、mepsps、2mepsps、gat4601、gat4621、goxv247;对于草铵膦耐受性:pat和bar,对于2,4-D耐受性:aad-1、aad-12;对于麦草畏耐受性:dmo;对于oxynil除草剂耐受性:bxn;对于磺酰脲除草剂耐受性:zm-hra、csr1-2、gm-hra、S4-HrA;对于ALS抑制剂耐受性:csr1-2;以及对于HPPD抑制剂耐受性:hppdPF、W336、avhppd-03。
包含除草剂耐受性基因的转基因玉米事件包括但不限于DAS40278,MON801,MON802,MON809,MON810,MON832,MON87411,MON87419,MON87427,MON88017,MON89034,NK603,GA21,MZHG0JG,HCEM485,VCO--5,676,678,680,33121,4114,59122,98140,Bt10,Bt176,CBH-351,DBT418,DLL25,MS3,MS6,MZIR098,T25,TC1507和TC6275。包含除草剂耐受性基因的转基因大豆事件包括但不限于GTS 40-3-2,MON87705,MON87708,MON87712,MON87769,MON89788,A2704-12,A2704-21,A5547-127,A5547-35,DP356043,DAS44406-6,DAS68416-4,DAS-81419-2,GU262,SYHT/>W62,W98,FG72和CV127。包含除草剂耐受性基因的转基因棉花事件包括但不限于19-51a,31707,42317,81910,281-24-236,3006-210-23,BXN10211,BXN10215,BXN10222,BXN10224,MON1445,MON1698,MON88701,MON88913,GHB119,GHB614,LLCotton25,T303-3和T304-40。包含除草剂耐受性基因的转基因卡罗拉事件例如为MON88302,HCR-1,HCN10,HCN28,HCN92,MS1,MS8,PHY14,PHY23,PHY35,PHY36,RF1,RF2和RF3,但不排除其他。
提供昆虫抗性的转基因优选是芽孢杆菌属(Bacillus spp.)的毒素基因及其合成变体,如cry1A,cry1Ab,cry1Ab-Ac,cry1Ac,cry1A.105,cry1F,cry1Fa2,cry2Ab2,cry2Ae,mcry3A,ecry3.1Ab,cry3Bb1,cry34Ab1,cry35Ab1,cry9C,vip3A(a),vip3Aa20。此外,可以使用植物来源的转基因,如编码蛋白酶抑制剂的基因,如CpTI和pinII。另一方法使用转基因如dvsnf7在植物中产生双链RNA。
包含杀虫蛋白基因或双链RNA的转基因玉米事件包括但不限于Bt10,Bt11,Bt176,MON801,MON802,MON809,MON810,MON863,MON87411,MON88017,MON89034,33121,4114,5307,59122,TC1507,TC6275,CBH-351,MIR162,DBT418和MZIR098。包含杀虫蛋白基因的转基因大豆事件包括但不限于MON87701,MON87751和DAS-81419。包含杀虫蛋白基因的转基因棉花事件包括但不限于SGK321,MON531,MON757,MON1076,MON15985,31707,3253,3257,3258,42317,BNLA-601,Event1,COT67B,COT102,T303-3,T304-40,GFM Cry1A,GK12,MLS9124,281-24-236,3006-210-23,GHB119和SGK321。
具有提高产量的栽培植物通过使用转基因athb17(例如玉米事件MON87403)或bbx32(例如大豆事件MON87712)产生。
包含改性含油量的栽培植物已经通过使用转基因:gm-fad2-1,Pj.D6D,Nc.Fad3、fad2-1A和fatb1-A产生(例如大豆事件260-05,MON87705和MON87769)。
对非生物条件如干旱的耐受性通过使用转基因cspB(玉米事件MON87460)和Hahb-4(大豆事件IND--5)产生。
通常通过在转化事件中将基因组合或者通过在育种工艺过程中将不同事件组合而将性状组合,得到具有堆叠性状的栽培植物。性状的优选组合是对不同类除草剂的除草剂耐受性性状组合,对不同种类昆虫的昆虫耐受性组合,尤其是对鳞翅目和鞘翅目昆虫的耐受性组合,除草剂耐受性与一种或几种类型昆虫抗性的组合,除草剂耐受性与提高的产量的组合以及除草剂耐受性和非生物条件耐受性的组合。
包含单独或堆叠性状的植物以及提供这些性状的基因和事件在本领域是众所周知的。例如,有关诱变或整合基因和相应事件的详细信息可以由组织机构“InternationalService for the Acquisition of Agri-biotech Applications(ISAAA)”(http://www.isaaa.org/gmapprovaldatabase)和“Center for Environmental Risk Assessment(CERA)”(http://cera-gmc.org/GMCropDatabase)的网站得到。有关特定事件和检测它们的方法的其他信息可以在如下文献中找到:对于卡罗拉事件MS1,MS8,RF3,GT73,MON88302,KK179在WO 01/031042,WO 01/041558,WO 01/041558,WO 02/036831,WO 11/153186,WO13/003558中找到;对于棉花事件MON1445,MON15985,MON531(MON15985),LLCotton25,MON88913,COT102,281-24-236,3006-210-23,COT67B,GHB614,T304-40,GHB119,MON88701,81910在WO 02/034946,WO 02/100163,WO 02/100163,WO 03/013224,WO 04/072235,WO04/039986,WO 05/103266,WO 05/103266,WO 06/128573,WO 07/017186,WO 08/122406,WO08/151780,WO 12/134808,WO 13/112527中找到;对于玉米事件GA21,MON810,DLL25,TC1507,MON863,MIR604,LY038,MON88017,3272,59122,NK603,MIR162,MON89034,98140,32138,MON87460,5307,4114,MON87427,DAS40278,MON87411,33121,MON87403,MON87419在WO98/044140,US02/102582,US03/126634,WO 04/099447,WO 04/011601,WO 05/103301,WO05/061720,WO 05/059103,WO 06/098952,WO 06/039376,US2007/292854,WO 07/142840,WO 07/140256,WO 08/112019,WO 09/103049,WO 09/111263,WO 10/077816,WO 11/084621,WO 11/062904,WO 11/022469,WO 13/169923,WO 14/116854,WO 15/053998,WO15/142571中找到;对于土豆事件E12,F10,J3,J55,V11,X17,Y9在WO 14/178910,WO 14/178913,WO 14/178941,WO 14/179276,WO 16/183445,WO 17/062831,WO 17/062825中找到;对于水稻事件LLRICE06,LLRICE601,LLRICE62在WO 00/026345,WO 00/026356,WO 00/026345中找到;以及对于大豆事件H7-1,MON89788,A2704-12,A5547-127,DP305423,DP356043,MON87701,MON87769,CV127,MON87705,DAS68416-4,MON87708,MON87712,SYHT0H2,DAS81419,DAS81419 x DAS44406-6,MON87751在WO 04/074492,WO 06/130436,WO06/108674,WO 06/108675,WO 08/054747,WO 08/002872,WO 09/064652,WO 09/102873,WO10/080829,WO 10/037016,WO 11/066384,WO 11/034704,WO 12/051199,WO 12/082548,WO13/016527,WO 13/016516,WO 14/201235中找到。
在栽培植物上分别使用化合物I及其组合物可能导致对包含某些转基因或事件的栽培植物呈特异性的效果。这些效果可能涉及生长行为的变化或对生物或非生物逆境因素的耐受性变化。该类效果尤其可能包括提高的产量,提高的昆虫、线虫、真菌、细菌、支原体、病毒或类病毒病原体抗性或耐受性以及早期活力、早熟或延迟成熟、冷或热耐受性以及氨基酸或脂肪酸谱或含量变化。
化合物I及其组合物分别特别适合防治下列植物病害的下列致病病原:观赏植物、蔬菜(例如白锈菌(A.candida))和向日葵(例如婆罗门参白锈菌(A.tragopogonis))上的白锈菌属(Albugo)(白锈病);蔬菜(例如胡萝卜黑斑病(A.dauci)或大葱紫斑病(A.porri))、油菜(例如芸苔生链格孢(A.brassicicola)或芸苔链格孢(A.brassicae))、糖用甜菜(例如细链格孢(A.tenuis))、水果(例如巨链格孢(A.grandis))、稻、大豆、土豆和西红柿(例如早疫链格孢(A.solani)、巨链格孢(A.grandis)或链格孢(A.alternata))、西红柿(例如早疫链格孢或链格孢)和小麦(例如小麦链格孢(A.triticina))上的链格孢属(Alternaria)(链格孢叶斑病);糖用甜菜和蔬菜上的丝囊霉属(Aphanomyces);禾谷类和蔬菜上的壳二孢属(Ascochyta),例如小麦上的A.tritici(炭疽病)和大麦上的大麦壳二孢(A.hordei);玉米上的玉米北方炭疽病菌(Aureobasidium zeae)(同义词玉米眼斑病菌(Kapatiellazeae));平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera)(有性型:旋孢腔菌属(Cochliobolus)),例如玉米上的叶斑病(玉蜀黍平脐蠕孢(D.maydis)或玉米生离蠕孢(B.zeicola)),例如禾谷类上的斑枯病(麦根腐平脐蠕孢(B.sorokiniana)以及例如稻和草坪上的稻平脐蠕孢(B.oryzae);禾谷类(例如小麦或大麦)上的小麦白粉菌(Blumeria(旧名:Erysiphe)graminis)(白粉病);水果和浆果(例如草莓)、蔬菜(例如莴苣、胡萝卜、根芹菜和卷心菜)(洋葱科上的葱鳞葡萄孢(B.squamosal)或葱腐葡萄孢(B.allii)、油菜或观赏植物(例如百合灰霉病(B eliptica))、葡萄藤、森林植物和小麦上的灰葡萄孢(Botrytiscinerea)(有性型:灰葡萄孢霉(Botryotinia fuckeliana):灰霉病);莴苣上的莴苣盘梗霉(Bremia lactucae)(霜霉病);阔叶树和常绿树上的长喙壳属(Ceratocystis)(同义词线嘴壳属(Ophiostoma))(腐烂病或枯萎病),例如榆树上的榆枯萎病菌(C.ulmi)(荷兰榆病);玉米(例如灰叶斑病:玉米尾孢菌(C.zeae-maydis))、稻、糖用甜菜(例如甜菜生尾孢(C.beticola))、甘蔗、蔬菜、咖啡、大豆(例如大豆灰斑病菌(C.sojina)或大豆紫斑病菌(C.kikuchii))和稻上的尾孢属(Cercospora)(尾孢叶斑病);蘑菇上的Cladobotryum spp.(同义词指孢霉属(Dactylium))(例如C.mycophilum(旧名:树状指孢霉(Dactyliumdendroides),有性型:Nectria albertinii,Nectria rosella,同义词粉红寄生菌(Hypomyces rosellus));西红柿(例如番茄叶霉菌(C.fulvum):叶霉病)和禾谷类(例如小麦上的草芽枝孢(C.herbarum)(穗腐病))上的枝孢属(Cladosporium);禾谷类上的麦角菌(Claviceps purpurea)(麦角病);玉米(灰色长蠕孢(C.carbonum))、禾谷类(例如禾旋孢腔菌(C.sativus),无性型:麦根腐平脐蠕孢)和稻(例如宫部旋孢腔菌(C.miyabeanus),无性型:水稻长蠕孢(H.oryzae))上的旋孢腔菌属(无性型:长蠕孢属(Helminthosporium)或平脐蠕孢属)(叶斑病);棉花(例如棉炭疽病菌(C.gossypii))、玉米(例如禾生炭疽病菌(C.graminicola):炭疽茎腐病)、浆果、土豆(例如西瓜炭疽病菌(C.coccodes):黑点病)、菜豆(例如菜豆炭疽病菌(C.lindemuthianum))、大豆(例如大豆炭疽病菌(C.truncatum)或毛豆炭疽病菌(C.gloeosporioides))、蔬菜(例如黄瓜炭疽病菌(C.lagenarium)或辣椒炭疽病菌(C.capsici))、水果(例如尖孢炭疽菌(C.acutatum))、咖啡(例如咖啡刺盘孢(C.coffeanum)或卡哈瓦刺盘孢(C.kahawae))和各种作物(胶孢炭疽菌(C.gloeosporioides)上的剌盘孢属(Colletotrichum)(有性型:围小丛壳菌属(Glomerella))(炭疽病);伏革菌属(Corticium),例如稻上的笹木伏革菌(C.sasakii)(纹枯病);大豆、棉花和观赏植物上的黄瓜褐斑病菌(Corynespora cassiicola)(叶斑病);锈斑病菌属(Cycloconium),例如橄榄树上的油橄榄孔雀斑病(C.oleaginum);果树、葡萄藤(例如C.liriodendri,有性型:Neonectria liriodendri:乌脚病)和观赏植物上的人参生柱隔孢属(Cylindrocarpon)(例如果树腐烂病或葡萄藤乌脚病,有性型:丛赤壳属(Nectria)或杓兰菌根菌属(Neonectria));大豆上的白纹羽菌(Dematophora(有性型:Rosellinia)necatrix)(根腐病/茎腐病);北茎溃疡菌属(Diaporthe),例如大豆上的大豆北茎溃疡病菌(D.phaseolorum)(立枯疡);玉米、禾谷类如大麦(例如大麦网斑内脐蠕孢(D.teres),网斑病)和小麦(例如D.tritici-repentis:褐斑病)、稻和草坪上的内脐蠕孢属(同义词长蠕孢属,有性型:核腔菌属(Pyrenophora));由斑褐孔菌(Formitiporia(同义词Phellinus)punctata)、地中海嗜蓝孢孔菌(F.mediterranea)、Phaeomoniellachlamydospora(旧名:Phaeoacremonium chlamydosporum)、Phaeoacremonium aleophilum和/或葡萄座腔菌(Botryosphaeria obtuse)引起的葡萄藤上的埃斯卡(Esca)(葡萄藤枯萎病,干枯病);仁果(E.pyri)、浆果(覆盆子痂囊腔菌(E.veneta):炭疽病)和葡萄藤(葡萄痂囊腔菌(E.ampelina):炭疽病)上的痂囊腔菌属(Elsinoe);稻上的稻叶黑粉菌(Entylomaoryzae)(叶黑粉病);小麦上的附球菌属(Epicoccum)(黑穗病);糖用甜菜(甜菜白粉菌(E.betae))、蔬菜(例如豌豆白粉菌(E.pisi))如葫芦科植物(例如二孢白粉菌(E.cichoracearum))、卷心菜、油菜(例如E.cruciferarum)上的白粉菌属(Erysiphe)(白粉病);果树、葡萄藤和观赏树上的侧弯孢菌(Eutypa lata)(Eutypa溃疡病或枯萎病,无性型:Cytosporina lata,同义词Libertella blepharis);玉米(例如玉米大斑病菌(E.turcicum))上的突脐蠕孢属(Exserohilum)(同义词长蠕孢属);各种植物上的镰孢霉属(Fusarium)(有性型:赤霉属(Gibberella))(枯萎病,根腐病或茎腐病),例如禾谷类(例如小麦或大麦)上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)(根腐病、黑星病或银尖病),西红柿上的尖镰孢(F.oxysporum),大豆上的茄镰孢(F.solani)(甘氨酸镰刀菌(f.sp.glycines),现在的同义词为北美大豆猝死综合症病菌(F.virguliforme)及各自引起猝死综合症的南美大豆猝死综合症病菌(F.tucumaniae)和巴西镰刀菌(F.brasiliense)以及玉米上的轮枝镰孢(F.verticillioides);禾谷类(例如小麦或大麦)和玉米上的禾顶囊壳(Gaeumannomyces graminis)(全蚀病);禾谷类(例如玉蜀黍赤霉(G.zeae))和稻(例如藤仓赤霉(G.fujikuroi):恶苗病)上的赤霉属;葡萄藤、仁果和其他植物上的苹果炭疽病菌(Glomerella cingulata)以及棉花上的棉炭疽病菌(G.gossypii);稻上的Grainstainingcomplex;葡萄藤上的葡萄黑腐病菌(Guignardia bidwellii)(黑腐病);蔷薇科植物和刺柏上的锈菌属(Gymnosporangium),例如梨上的G.sabinae(锈病);玉米、禾谷类、土豆和稻上的长蠕孢属(同义词内脐蠕孢属,有性型:旋孢腔菌属);驼孢锈菌属(Hemileia),例如咖啡上的咖啡驼孢锈菌(H.vastatrix)(咖啡叶锈病);葡萄藤上的褐斑拟棒束孢(Isariopsisclavispora)(同义词Cladosporium vitis);大豆和棉花上的菜豆壳球孢(Macrophominaphaseolina(同义词phaseoli))(根腐病/茎腐病);禾谷类(例如小麦或大麦)上的雪霉叶枯菌(Microdochium(同义词Fusarium)nivale(雪霉病);大豆上的扩散叉丝壳(Microsphaeradiffusa)(白粉病);丛梗孢属(Monilinia),例如核果和其他蔷薇科植物上的核果链核盘菌(M.laxa)、桃褐腐菌(M.fructicola)和M.fructigena(同义词丛梗孢属(Monilia spp.):花腐病和枝腐病,褐腐病);禾谷类、香蕉、浆果和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)(无性型:叶枯病菌(Zymoseptoria tritici),旧名:小麦壳针孢(Septoria tritici),壳针孢叶斑病)或香蕉上的斐济球腔菌(M.fijiensis)(同义词Pseudocercospora fijiensis:Sigatoka黑斑病)和香蕉黄条叶斑病菌(M.musicola),花生上的花生球腔菌(M.arachidicola)(同义词花生褐斑病菌(M.arachidis)或Cercospora arachidis),伯克利球腔菌(M.berkeleyi),豌豆上的M.pisi和芥属植物上的M.brassiciola;卷心菜(例如芸苔霜霉(P.brassicae))、油菜(例如寄生霜霉(P.parasitica))、洋葱(例如大葱霜霉(P.destructor))、烟草(烟草霜霉(P.tabacina))和大豆(例如大豆霜霉病菌(P.manshurica))上的霜霉属(Peronospora)(霜霉病);大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.meibomiae)(大豆锈病);例如葡萄藤(例如P.tracheiphila和P.tetraspora)和大豆(例如大豆茎褐腐病菌(P.gregata):茎病害)上的瓶霉菌属(Phialophora);油菜和卷心菜上的黑胫茎点霉(Phoma lingam)(同义词黑胫病菌(Leptosphaeria biglobosa)和斑点小球腔菌(L.maculans):根腐病和茎腐病),糖用甜菜上的甜菜茎点霉(P.betae)(根腐病、叶斑病和立枯疡)以及玉米上的P.zeae-maydis(同义词Phyllostica zeae);向日葵、葡萄藤(例如葡萄黑腐病菌(P.viticola):蔓割病和叶斑病)和大豆(例如茎腐病:菜豆拟茎点霉(P.phaseoli),有性型:大豆北茎溃疡病菌(Diaporthe phaseolorum))上的拟茎点霉属(Phomopsis);玉米上的玉米褐斑病菌(Physoderma maydis)(褐斑病);各种植物如柿子椒和葫芦科植物(例如辣椒疫霉(P.capsici))、大豆(例如大豆疫霉(P.megasperma),同义词大豆疫霉菌(P.sojae))、土豆和西红柿(例如致病疫霉(P.infestans):晚疫病)和阔叶树(例如栎树猝死病菌(P.ramorum):橡树急死病)上的疫霉属(Phytophthora)(枯萎病,根腐病,叶腐病,果树腐烂病和茎腐病);卷心菜、油菜、小萝卜和其他植物上的芸苔根肿菌(Plasmodiophorabrassicae)(根肿病);霜霉属(Plasmopara),例如葡萄藤上的葡萄生单轴霉(P.viticola)(葡萄藤霜霉病)和向日葵上的霍尔斯单轴霉(P.halstedii);蔷薇科植物、啤酒花、仁果和浆果(例如苹果上的苹果白粉病菌(P.leucotricha))以及葫芦科植物(甜瓜白粉病(P.xanthii))上的叉丝单囊壳属(Podosphaera)(白粉病);例如禾谷类如大麦和小麦(禾谷多粘菌(P.graminis))以及糖用甜菜(甜菜多粘菌(P.betae))上的多粘菌属(Polymyxa)以及由此传播的病毒病害;禾谷类如小麦或大麦上的小麦基腐病菌(Pseudocercosporellaherpotrichoides)(同义词Oculimacula yallundae,O.acuformis:眼斑病,有性型:Tapesia yallundae);各种植物上的假霜霉属(Pseudoperonospora)(霜霉病),例如葫芦科植物上的古巴假霜霉(P.cubensis)或啤酒花上的葎草假霜(P.humili);葡萄藤上的Pseudopezicula tracheiphila(葡萄角斑叶焦病菌或‘rotbrenner’,无性型:瓶霉属(Phialophora));各种植物上的柄锈菌属(Puccinia)(锈病),例如禾谷类如小麦、大麦或黑麦上的小麦柄锈菌(P.triticina)(褐锈病或叶锈病),条形柄锈病(P.striiformis)(条纹病或黄锈病),大麦柄锈病(P.hordei)(大麦黄矮叶锈病),禾柄锈菌(P.graminis)(茎腐病或黑锈病)或小麦叶锈菌(P.recondita)(褐锈病或叶锈病),甘蔗上的屈恩柄锈菌(P.kuehnii)(橙锈病)和芦笋上的天门冬属柄锈病(P.asparagi);油菜上的核盘菌属(Pyrenopeziza spp.),例如P.brassicae;小麦上的小麦黄斑叶枯病菌(Pyrenophora(无性型:Drechslera)tritici-repentis)(黄斑病)或大麦上的圆核腔菌(P.teres)(网斑病);梨孢属(Pyricularia),例如稻上的稻瘟病菌(P.oryzae)(有性型:Magnaporthe grisea,稻瘟病)以及草坪和禾谷类上的稻梨孢菌(P.grisea);草坪、稻、玉米、小麦、棉花、油菜、向日葵、大豆、糖用甜菜、蔬菜和各种其他植物(例如终极腐霉菌(P.ultimum)或瓜果腐霉(P.aphanidermatum))和蘑菇(寡雄腐霉(P.oligandrum))上的腐霉属(Pythium)(立枯病);柱隔孢属(Ramularia),例如大麦上的辛加柱隔孢(R.collo-cygni)(柱隔孢叶斑病,生理叶斑病),棉花上的白斑柱隔孢(R.areola)(有性型:网孢球腔菌(Mycosphaerella areola))和糖用甜菜上的甜菜叶斑病菌(R.beticola);棉花、稻、土豆、草坪、玉米、油菜、土豆、糖用甜菜、蔬菜和各种其他植物上的丝核菌属(Rhizoctonia),例如大豆上的立枯丝核菌(R.solani)(根腐病/茎腐病),稻上的立枯丝核菌(纹枯病)或小麦或大麦上的禾谷丝核菌(R.cerealis)(小麦纹枯病);草莓、胡萝卜、卷心菜、葡萄藤和西红柿上的葡枝根霉(Rhizopus stolonifer)(黑霉病,软腐病);大麦、黑麦和小黑麦上的黑麦喙孢(Rhynchosporium secalis)和R.commune(叶斑病);稻上的稻帚枝霉(Sarocladiumoryzae)和S.attenuatum(叶鞘腐败病);蔬菜(小核盘菌(S.minor)和核盘菌(S.sclerotiorum))和大田作物如油菜、向日葵(例如核盘菌(S.sclerotiorum))以及大豆、花生、蔬菜、玉米、禾谷类和观赏植物(白绢病(S.rolfsii)(同义词罗耳阿太菌(Atheliarolfsii))上的核盘菌属(Sclerotinia)(茎腐病或白绢病);各种植物上的壳针孢属(Septoria),例如大豆上的大豆壳针孢(S.glycines)(褐斑病),小麦上的小麦壳针孢(S.tritici)(同义词叶枯病菌(Zymoseptoria tritici),壳针孢叶斑病)和禾谷类上的颖枯壳多孢(S.(同义词Stagonospora)nodorum)(斑枯病);葡萄藤上的葡萄钩丝壳(Uncinula(同义词Erysiphe)necator)(白粉病,无性型:葡萄粉孢(Oidium tuckeri));玉米(例如玉米大斑病菌(S.turcicum),同义词大斑凸脐蠕孢(Helminthosporium turcicum))和草坪上的大斑病菌属(Setosphaeria)(叶枯病);玉米(例如丝轴黑粉菌(S.reiliana),同义词Ustilago reiliana:丝黑穗病)、高粱和甘蔗上的轴黑粉菌属(Sphacelotheca)(黑穗病);葫芦科植物上的单丝壳白粉菌(Sphaerotheca fuliginea)(同义词甜瓜白粉病(Podosphaera xanthii):白粉病);土豆上的粉痂菌(Spongospora subterranea)(粉痂病)以及由此传播的病毒病害;禾谷类上的壳多孢属(Stagonospora),例如小麦上的颖枯壳多孢(S.nodorum)(斑枯病,有性型:颖枯球腔菌(Leptosphaeria[同义词Phaeosphaeria]nodorum),同义词颖枯壳多孢(Septoria nodorum));土豆上的马铃薯癌肿病菌(Synchytrium endobioticum)(土豆癌肿病);外囊菌属(Taphrina),例如桃上的畸形外囊菌(T.deformans)(缩叶病)和李上的李外囊菌(T.pruni)(囊果李);烟草、仁果、蔬菜、大豆和棉花上的根串珠霉属(Thielaviopsis)(黑色根腐病),例如黑色根腐病菌(T.basicola)(同义词根黑腐病(Chalara elegans));禾谷类上的腥黑粉菌属(Tilletia)(腥黑穗病或光腥黑穗病),例如小麦上的小麦腥黑粉菌(T.tritici)(同义词小麦网腥黑粉菌(T.caries),小麦腥黑穗病)和小麦矮腥黑穗病(T.controversa)(矮腥黑穗病);蘑菇上的哈茨木霉菌(Trichoderma harzianum);大麦或小麦上的肉孢核瑚菌(Typhula incarnata)(灰雪腐病);黑粉菌属(Urocystis),例如黑麦上的隐条黑粉菌(U.occulta)(条黑粉病);蔬菜如菜豆(例如疣顶单胞锈菌(U.appendiculatus),同义词U.phaseoli)、糖用甜菜(例如甜菜锈病菌(U.betae)或U.beticola))和豆类(例如豇豆锈菌(U.vignae)、豌豆锈菌(U.pisi)、蚕豆单孢锈菌(U.viciae-fabae)和蚕豆锈菌(U.fabae))上的单孢锈属(Uromyces)(锈病);禾谷类(例如大麦散黑粉菌(U.nuda)和燕麦散黑粉菌(U.avaenae))、玉米(例如玉蜀黍黑粉菌(U.maydis):玉米黑穗病)和甘蔗上的黑粉菌属(Ustilago)(黑穗病);苹果(例如苹果黑星病(V.inaequalis))和梨上的黑星菌属(Venturia)(黑星病);以及各种植物如果树和观赏树、葡萄藤、浆果、蔬菜和大田作物上的轮生菌属(Verticillium)(枯萎病),例如油菜上的油菜黄萎菌(V.longisporum),草莓、油菜、土豆和西红柿上的茄黄萎病菌(V.dahliae)及蘑菇上的蘑菇褐腐病(V.fungicola);禾谷类上的叶枯病菌(Zymoseptoria tritici)。
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病原: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;小麦上的小麦柄锈菌(Pucciniatritici)和条形柄锈病);特种作物、大豆、油菜和向日葵上的霉病(例如草莓和葡萄藤上的灰葡萄孢,油菜、向日葵和大豆上的核盘菌(Sclerotinia sclerotiorum)、小核盘菌和白绢病);禾谷类上的镰孢霉病(例如小麦上的大刀镰孢(Fusarium culmorum)和禾本科镰孢);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,各种特种作物上的白粉菌属,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,大豆上的大豆壳针孢,玉米和大豆上的尾孢属)。
根据一个实施方案,化合物I.A-1.1a.B-1至I.A-1.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.1a.B-1至I.A-2.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.1a.B-1至I.A-3.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.1a.B-1至I.A-4.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.2a.B-1至I.A-1.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.2a.B-1至I.A-2.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.2a.B-1至I.A-3.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.2a.B-1至I.A-4.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.3a.B-1至I.A-1.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.3a.B-1至I.A-2.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.3a.B-1至I.A-3.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.3a.B-1至I.A-4.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.4a.B-1至I.A-1.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.4a.B-1至I.A-2.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.4a.B-1至I.A-3.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.4a.B-1至I.A-4.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.5a.B-1至I.A-1.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.5a.B-1至I.A-2.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.5a.B-1至I.A-3.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.5a.B-1至I.A-4.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.6a.B-1至I.A-1.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.6a.B-1至I.A-2.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.6a.B-1至I.A-3.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.6a.B-1至I.A-4.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-1.7a.B-1至I.A-1.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-2.7a.B-1至I.A-2.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-3.7a.B-1至I.A-3.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.A-4.7a.B-1至I.A-4.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.1a.B-1至I.B-1.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.1a.B-1至I.B-2.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.1a.B-1至I.B-3.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.1a.B-1至I.B-4.1a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.2a.B-1至I.B-1.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.2a.B-1至I.B-2.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.2a.B-1至I.B-3.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.2a.B-1至I.B-4.2a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.3a.B-1至I.B-1.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.3a.B-1至I.B-2.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.3a.B-1至I.B-3.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.3a.B-1至I.B-4.3a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.4a.B-1至I.B-1.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.4a.B-1至I.B-2.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.4a.B-1至I.B-3.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.4a.B-1至I.B-4.4a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.5a.B-1至I.B-1.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.5a.B-1至I.B-2.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.5a.B-1至I.B-3.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.5a.B-1至I.B-4.5a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.6a.B-1至I.B-1.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.6a.B-1至I.B-2.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.6a.B-1至I.B-3.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.6a.B-1至I.B-4.6a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-1.7a.B-1至I.B-1.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-2.7a.B-1至I.B-2.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-3.7a.B-1至I.B-3.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物I.B-4.7a.B-1至I.B-4.7a.B-25特别适合防治根据清单Z的植物病害的致病病原。
根据一个实施方案,化合物Ex-1至Ex-101特别适合防治根据清单Z的植物病害的致病病原。
清单Z:
观赏植物、蔬菜(例如白锈菌(A.candida))和向日葵(例如婆罗门参白锈菌(A.tragopogonis))上的白锈菌属(Albugo)(白锈病);蔬菜(例如胡萝卜黑斑病(A.dauci)或大葱紫斑病(A.porri))、油菜(例如芸苔生链格孢(A.brassicicola)或芸苔链格孢(A.brassicae))、糖用甜菜(例如细链格孢(A.tenuis))、水果(例如巨链格孢(A.grandis))、稻、大豆、土豆和西红柿(例如早疫链格孢(A.solani)、巨链格孢(A.grandis)或链格孢(A.alternata))、西红柿(例如早疫链格孢或链格孢)和小麦(例如小麦链格孢(A.triticina))上的链格孢属(Alternaria)(链格孢叶斑病);糖用甜菜和蔬菜上的丝囊霉属(Aphanomyces);禾谷类和蔬菜上的壳二孢属(Ascochyta),例如小麦上的A.tritici(炭疽病)和大麦上的大麦壳二孢(A.hordei);玉米上的玉米北方炭疽病菌(Aureobasidium zeae)(同义词玉米眼斑病菌(Kapatiella zeae));平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera)(有性型:旋孢腔菌属(Cochliobolus)),例如玉米上的叶斑病(玉蜀黍平脐蠕孢(D.maydis)或玉米生离蠕孢(B.zeicola)),例如禾谷类上的斑枯病(麦根腐平脐蠕孢(B.sorokiniana)以及例如稻和草坪上的稻平脐蠕孢(B.oryzae);禾谷类(例如小麦或大麦)上的小麦白粉菌(Blumeria(旧名:Erysiphe)graminis)(白粉病);水果和浆果(例如草莓)、蔬菜(例如莴苣、胡萝卜、根芹菜和卷心菜)(洋葱科上的葱鳞葡萄孢(B.squamosal)或葱腐葡萄孢(B.allii)、油菜或观赏植物(例如百合灰霉病(Beliptica))、葡萄藤、森林植物和小麦上的灰葡萄孢(Botrytis cinerea)(有性型:灰葡萄孢霉(Botryotinia fuckeliana):灰霉病);莴苣上的莴苣盘梗霉(Bremia lactucae)(霜霉病);阔叶树和常绿树上的长喙壳属(Ceratocystis)(同义词线嘴壳属(Ophiostoma))(腐烂病或枯萎病),例如榆树上的榆枯萎病菌(C.ulmi)(荷兰榆病);玉米(例如灰叶斑病:玉米尾孢菌(C.zeae-maydis))、稻、糖用甜菜(例如甜菜生尾孢(C.beticola))、甘蔗、蔬菜、咖啡、大豆(例如大豆灰斑病菌(C.sojina)或大豆紫斑病菌(C.kikuchii))和稻上的尾孢属(Cercospora)(尾孢叶斑病);蘑菇上的Cladobotryum spp.(同义词指孢霉属(Dactylium))(例如C.mycophilum(旧名:树状指孢霉(Dactylium dendroides),有性型:Nectriaalbertinii,Nectria rosella,同义词粉红寄生菌(Hypomyces rosellus));西红柿(例如番茄叶霉菌(C.fulvum):叶霉病)和禾谷类(例如小麦上的草芽枝孢(C.herbarum)(穗腐病))上的枝孢属(Cladosporium);禾谷类上的麦角菌(Claviceps purpurea)(麦角病);玉米(灰色长蠕孢(C.carbonum))、禾谷类(例如禾旋孢腔菌(C.sativus),无性型:麦根腐平脐蠕孢)和稻(例如宫部旋孢腔菌(C.miyabeanus),无性型:水稻长蠕孢(H.oryzae))上的旋孢腔菌属(无性型:长蠕孢属(Helminthosporium)或平脐蠕孢属)(叶斑病);棉花(例如棉炭疽病菌(C.gossypii))、玉米(例如禾生炭疽病菌(C.graminicola):炭疽茎腐病)、浆果、土豆(例如西瓜炭疽病菌(C.coccodes):黑点病)、菜豆(例如菜豆炭疽病菌(C.lindemuthianum))、大豆(例如大豆炭疽病菌(C.truncatum)或毛豆炭疽病菌(C.gloeosporioides))、蔬菜(例如黄瓜炭疽病菌(C.lagenarium)或辣椒炭疽病菌(C.capsici))、水果(例如尖孢炭疽菌(C.acutatum))、咖啡(例如咖啡刺盘孢(C.coffeanum)或卡哈瓦刺盘孢(C.kahawae))和各种作物(胶孢炭疽菌(C.gloeosporioides)上的剌盘孢属(Colletotrichum)(有性型:围小丛壳菌属(Glomerella))(炭疽病);伏革菌属(Corticium),例如稻上的笹木伏革菌(C.sasakii)(纹枯病);大豆、棉花和观赏植物上的黄瓜褐斑病菌(Corynespora cassiicola)(叶斑病);锈斑病菌属(Cycloconium),例如橄榄树上的油橄榄孔雀斑病(C.oleaginum);果树、葡萄藤(例如C.liriodendri,有性型:Neonectria liriodendri:乌脚病)和观赏植物上的人参生柱隔孢属(Cylindrocarpon)(例如果树腐烂病或葡萄藤乌脚病,有性型:丛赤壳属(Nectria)或杓兰菌根菌属(Neonectria));大豆上的白纹羽菌(Dematophora(有性型:Rosellinia)necatrix)(根腐病/茎腐病);北茎溃疡菌属(Diaporthe),例如大豆上的大豆北茎溃疡病菌(D.phaseolorum)(立枯疡);玉米、禾谷类如大麦(例如大麦网斑内脐蠕孢(D.teres),网斑病)和小麦(例如D.tritici-repentis:褐斑病)、稻和草坪上的内脐蠕孢属(同义词长蠕孢属,有性型:核腔菌属(Pyrenophora));由斑褐孔菌(Formitiporia(同义词Phellinus)punctata)、地中海嗜蓝孢孔菌(F.mediterranea)、Phaeomoniellachlamydospora(旧名:Phaeoacremonium chlamydosporum)、Phaeoacremonium aleophilum和/或葡萄座腔菌(Botryosphaeria obtuse)引起的葡萄藤上的埃斯卡(Esca)(葡萄藤枯萎病,干枯病);仁果(E.pyri)、浆果(覆盆子痂囊腔菌(E.veneta):炭疽病)和葡萄藤(葡萄痂囊腔菌(E.ampelina):炭疽病)上的痂囊腔菌属(Elsinoe);稻上的稻叶黑粉菌(Entylomaoryzae)(叶黑粉病);小麦上的附球菌属(Epicoccum)(黑穗病);糖用甜菜(甜菜白粉菌(E.betae))、蔬菜(例如豌豆白粉菌(E.pisi))如葫芦科植物(例如二孢白粉菌(E.cichoracearum))、卷心菜、油菜(例如E.cruciferarum)上的白粉菌属(Erysiphe)(白粉病);果树、葡萄藤和观赏树上的侧弯孢菌(Eutypa lata)(Eutypa溃疡病或枯萎病,无性型:Cytosporina lata,同义词Libertella blepharis);玉米(例如玉米大斑病菌(E.turcicum))上的突脐蠕孢属(Exserohilum)(同义词长蠕孢属);各种植物上的镰孢霉属(Fusarium)(有性型:赤霉属(Gibberella))(枯萎病,根腐病或茎腐病),例如禾谷类(例如小麦或大麦)上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)(根腐病、黑星病或银尖病),西红柿上的尖镰孢(F.oxysporum),大豆上的茄镰孢(F.solani)(甘氨酸镰刀菌(f.sp.glycines),现在的同义词为北美大豆猝死综合症病菌(F.virguliforme)及各自引起猝死综合症的南美大豆猝死综合症病菌(F.tucumaniae)和巴西镰刀菌(F.brasiliense)以及玉米上的轮枝镰孢(F.verticillioides);禾谷类(例如小麦或大麦)和玉米上的禾顶囊壳(Gaeumannomyces graminis)(全蚀病);禾谷类(例如玉蜀黍赤霉(G.zeae))和稻(例如藤仓赤霉(G.fujikuroi):恶苗病)上的赤霉属;葡萄藤、仁果和其他植物上的苹果炭疽病菌(Glomerella cingulata)以及棉花上的棉炭疽病菌(G.gossypii);稻上的Grainstainingcomplex;葡萄藤上的葡萄黑腐病菌(Guignardia bidwellii)(黑腐病);蔷薇科植物和刺柏上的锈菌属(Gymnosporangium),例如梨上的G.sabinae(锈病);玉米、禾谷类、土豆和稻上的长蠕孢属(同义词内脐蠕孢属,有性型:旋孢腔菌属);驼孢锈菌属(Hemileia),例如咖啡上的咖啡驼孢锈菌(H.vastatrix)(咖啡叶锈病);葡萄藤上的褐斑拟棒束孢(Isariopsisclavispora)(同义词Cladosporium vitis);大豆和棉花上的菜豆壳球孢(Macrophominaphaseolina(同义词phaseoli))(根腐病/茎腐病);禾谷类(例如小麦或大麦)上的雪霉叶枯菌(Microdochium(同义词Fusarium)nivale(雪霉病);大豆上的扩散叉丝壳(Microsphaeradiffusa)(白粉病);丛梗孢属(Monilinia),例如核果和其他蔷薇科植物上的核果链核盘菌(M.laxa)、桃褐腐菌(M.fructicola)和M.fructigena(同义词丛梗孢属(Monilia spp.):花腐病和枝腐病,褐腐病);禾谷类、香蕉、浆果和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)(无性型:叶枯病菌(Zymoseptoria tritici),旧名:小麦壳针孢(Septoria tritici),壳针孢叶斑病)或香蕉上的斐济球腔菌(M.fijiensis)(同义词Pseudocercospora fijiensis:Sigatoka黑斑病)和香蕉黄条叶斑病菌(M.musicola),花生上的花生球腔菌(M.arachidicola)(同义词花生褐斑病菌(M.arachidis)或Cercospora arachidis),伯克利球腔菌(M.berkeleyi),豌豆上的M.pisi和芥属植物上的M.brassiciola;卷心菜(例如芸苔霜霉(P.brassicae))、油菜(例如寄生霜霉(P.parasitica))、洋葱(例如大葱霜霉(P.destructor))、烟草(烟草霜霉(P.tabacina))和大豆(例如大豆霜霉病菌(P.manshurica))上的霜霉属(Peronospora)(霜霉病);大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(P.meibomiae)(大豆锈病);例如葡萄藤(例如P.tracheiphila和P.tetraspora)和大豆(例如大豆茎褐腐病菌(P.gregata):茎病害)上的瓶霉菌属(Phialophora);油菜和卷心菜上的黑胫茎点霉(Phoma lingam)(同义词黑胫病菌(Leptosphaeria biglobosa)和斑点小球腔菌(L.maculans):根腐病和茎腐病),糖用甜菜上的甜菜茎点霉(P.betae)(根腐病、叶斑病和立枯疡)以及玉米上的P.zeae-maydis(同义词Phyllostica zeae);向日葵、葡萄藤(例如葡萄黑腐病菌(P.viticola):蔓割病和叶斑病)和大豆(例如茎腐病:菜豆拟茎点霉(P.phaseoli),有性型:大豆北茎溃疡病菌(Diaporthe phaseolorum))上的拟茎点霉属(Phomopsis);玉米上的玉米褐斑病菌(Physoderma maydis)(褐斑病);各种植物如柿子椒和葫芦科植物(例如辣椒疫霉(P.capsici))、大豆(例如大豆疫霉(P.megasperma),同义词大豆疫霉菌(P.sojae))、土豆和西红柿(例如致病疫霉(P.infestans):晚疫病)和阔叶树(例如栎树猝死病菌(P.ramorum):橡树急死病)上的疫霉属(Phytophthora)(枯萎病,根腐病,叶腐病,果树腐烂病和茎腐病);卷心菜、油菜、小萝卜和其他植物上的芸苔根肿菌(Plasmodiophorabrassicae)(根肿病);霜霉属(Plasmopara),例如葡萄藤上的葡萄生单轴霉(P.viticola)(葡萄藤霜霉病)和向日葵上的霍尔斯单轴霉(P.halstedii);蔷薇科植物、啤酒花、仁果和浆果(例如苹果上的苹果白粉病菌(P.leucotricha))以及葫芦科植物(甜瓜白粉病(P.xanthii))上的叉丝单囊壳属(Podosphaera)(白粉病);例如禾谷类如大麦和小麦(禾谷多粘菌(P.graminis))以及糖用甜菜(甜菜多粘菌(P.betae))上的多粘菌属(Polymyxa)以及由此传播的病毒病害;禾谷类如小麦或大麦上的小麦基腐病菌(Pseudocercosporellaherpotrichoides)(同义词Oculimacula yallundae,O.acuformis:眼斑病,有性型:Tapesia yallundae);各种植物上的假霜霉属(Pseudoperonospora)(霜霉病),例如葫芦科植物上的古巴假霜霉(P.cubensis)或啤酒花上的葎草假霜(P.humili);葡萄藤上的Pseudopezicula tracheiphila(葡萄角斑叶焦病菌或‘rotbrenner’,无性型:瓶霉属(Phialophora));各种植物上的柄锈菌属(Puccinia)(锈病),例如禾谷类如小麦、大麦或黑麦上的小麦柄锈菌(P.triticina)(褐锈病或叶锈病),条形柄锈病(P.striiformis)(条纹病或黄锈病),大麦柄锈病(P.hordei)(大麦黄矮叶锈病),禾柄锈菌(P.graminis)(茎腐病或黑锈病)或小麦叶锈菌(P.recondita)(褐锈病或叶锈病),甘蔗上的屈恩柄锈菌(P.kuehnii)(橙锈病)和芦笋上的天门冬属柄锈病(P.asparagi);油菜上的核盘菌属(Pyrenopeziza spp.),例如P.brassicae;小麦上的小麦黄斑叶枯病菌(Pyrenophora(无性型:Drechslera)tritici-repentis)(黄斑病)或大麦上的圆核腔菌(P.teres)(网斑病);梨孢属(Pyricularia),例如稻上的稻瘟病菌(P.oryzae)(有性型:Magnaporthe grisea,稻瘟病)以及草坪和禾谷类上的稻梨孢菌(P.grisea);草坪、稻、玉米、小麦、棉花、油菜、向日葵、大豆、糖用甜菜、蔬菜和各种其他植物(例如终极腐霉菌(P.ultimum)或瓜果腐霉(P.aphanidermatum))和蘑菇(寡雄腐霉(P.oligandrum))上的腐霉属(Pythium)(立枯病);柱隔孢属(Ramularia),例如大麦上的辛加柱隔孢(R.collo-cygni)(柱隔孢叶斑病,生理叶斑病),棉花上的白斑柱隔孢(R.areola)(有性型:网孢球腔菌(Mycosphaerella areola))和糖用甜菜上的甜菜叶斑病菌(R.beticola);棉花、稻、土豆、草坪、玉米、油菜、土豆、糖用甜菜、蔬菜和各种其他植物上的丝核菌属(Rhizoctonia),例如大豆上的立枯丝核菌(R.solani)(根腐病/茎腐病),稻上的立枯丝核菌(纹枯病)或小麦或大麦上的禾谷丝核菌(R.cerealis)(小麦纹枯病);草莓、胡萝卜、卷心菜、葡萄藤和西红柿上的葡枝根霉(Rhizopus stolonifer)(黑霉病,软腐病);大麦、黑麦和小黑麦上的黑麦喙孢(Rhynchosporium secalis)和R.commune(叶斑病);稻上的稻帚枝霉(Sarocladiumoryzae)和S.attenuatum(叶鞘腐败病);蔬菜(小核盘菌(S.minor)和核盘菌(S.sclerotiorum))和大田作物如油菜、向日葵(例如核盘菌(S.sclerotiorum))以及大豆、花生、蔬菜、玉米、禾谷类和观赏植物(白绢病(S.rolfsii)(同义词罗耳阿太菌(Atheliarolfsii))上的核盘菌属(Sclerotinia)(茎腐病或白绢病);各种植物上的壳针孢属(Septoria),例如大豆上的大豆壳针孢(S.glycines)(褐斑病),小麦上的小麦壳针孢(S.tritici)(同义词叶枯病菌(Zymoseptoria tritici),壳针孢叶斑病)和禾谷类上的颖枯壳多孢(S.(同义词Stagonospora)nodorum)(斑枯病);葡萄藤上的葡萄钩丝壳(Uncinula(同义词Erysiphe)necator)(白粉病,无性型:葡萄粉孢(Oidium tuckeri));玉米(例如玉米大斑病菌(S.turcicum),同义词大斑凸脐蠕孢(Helminthosporium turcicum))和草坪上的大斑病菌属(Setosphaeria)(叶枯病);玉米(例如丝轴黑粉菌(S.reiliana),同义词Ustilago reiliana:丝黑穗病)、高粱和甘蔗上的轴黑粉菌属(Sphacelotheca)(黑穗病);葫芦科植物上的单丝壳白粉菌(Sphaerotheca fuliginea)(同义词甜瓜白粉病(Podosphaera xanthii):白粉病);土豆上的粉痂菌(Spongospora subterranea)(粉痂病)以及由此传播的病毒病害;禾谷类上的壳多孢属(Stagonospora),例如小麦上的颖枯壳多孢(S.nodorum)(斑枯病,有性型:颖枯球腔菌(Leptosphaeria[同义词Phaeosphaeria]nodorum),同义词颖枯壳多孢(Septoria nodorum));土豆上的马铃薯癌肿病菌(Synchytrium endobioticum)(土豆癌肿病);外囊菌属(Taphrina),例如桃上的畸形外囊菌(T.deformans)(缩叶病)和李上的李外囊菌(T.pruni)(囊果李);烟草、仁果、蔬菜、大豆和棉花上的根串珠霉属(Thielaviopsis)(黑色根腐病),例如黑色根腐病菌(T.basicola)(同义词根黑腐病(Chalara elegans));禾谷类上的腥黑粉菌属(Tilletia)(腥黑穗病或光腥黑穗病),例如小麦上的小麦腥黑粉菌(T.tritici)(同义词小麦网腥黑粉菌(T.caries),小麦腥黑穗病)和小麦矮腥黑穗病(T.controversa)(矮腥黑穗病);蘑菇上的哈茨木霉菌(Trichoderma harzianum);大麦或小麦上的肉孢核瑚菌(Typhula incarnata)(灰雪腐病);黑粉菌属(Urocystis),例如黑麦上的隐条黑粉菌(U.occulta)(条黑粉病);蔬菜如菜豆(例如疣顶单胞锈菌(U.appendiculatus),同义词U.phaseoli)、糖用甜菜(例如甜菜锈病菌(U.betae)或U.beticola))和豆类(例如豇豆锈菌(U.vignae)、豌豆锈菌(U.pisi)、蚕豆单孢锈菌(U.viciae-fabae)和蚕豆锈菌(U.fabae))上的单孢锈属(Uromyces)(锈病);禾谷类(例如大麦散黑粉菌(U.nuda)和燕麦散黑粉菌(U.avaenae))、玉米(例如玉蜀黍黑粉菌(U.maydis):玉米黑穗病)和甘蔗上的黑粉菌属(Ustilago)(黑穗病);苹果(例如苹果黑星病(V.inaequalis))和梨上的黑星菌属(Venturia)(黑星病);以及各种植物如果树和观赏树、葡萄藤、浆果、蔬菜和大田作物上的轮生菌属(Verticillium)(枯萎病),例如油菜上的油菜黄萎菌(V.longisporum),草莓、油菜、土豆和西红柿上的茄黄萎病菌(V.dahliae)及蘑菇上的蘑菇褐腐病(V.fungicola);禾谷类上的叶枯病菌(Zymoseptoria tritici)。
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。
术语“储存产品或收获产品”应理解为表示希望长期保护的植物或动物来源的天然物质及其加工形式。植物来源的储存产品,例如茎、叶、块茎、种子、果实或谷粒可以以新鲜收获状态或以加工形式保护,如预干燥、润湿、粉碎、研磨、压榨或烘焙,该方法也已知为收获后处理。也落入储存产品定义下的是木料,无论是未加工木料形式,如建筑木料、电线塔和栅栏,还是成品形式,如木制家具和物品。动物来源的储存产品是生皮、皮革、毛皮、毛发等。优选“储存产品”应理解为表示植物来源的天然物质或其加工形式,更优选果实及其加工形式,如仁果、核果、浆果和柑橘类水果及其加工形式,其中化合物I及其组合物的施用还可以防止不利的效果如腐败、变色或霉变。
术语“材料保护”应理解为表示保护工业和非活体材料,如粘合剂、胶、木材、纸张、纸板、纺织品、皮革、漆分散体、塑料、冷却润滑剂、纤维或织物以防有害微生物如真菌和细菌侵袭和破坏。
当用于保护材料或储存产品中时,活性物质的施用量取决于施用区域的种类和所需效果。在材料保护中常用的施用量例如为0.001g-2kg,优选0.005g-1kg活性物质/立方米被处理材料。
化合物I及其组合物分别可以用于改善植物健康。本发明还涉及一种通过分别用有效量的化合物I及其组合物处理植物、其繁殖材料和/或其中植物生长或要生长的场所而改善植物健康的方法。
术语“植物健康”应理解为表示植物和/或其产品由几种迹象如产量(例如增加的生物量和/或增加的有价值成分含量)、植物活力(例如改善的植物生长和/或更绿的叶子(“绿化效应”))、质量(例如某些成分的改善含量或组成)和对非生物和/或生物逆境的耐受性单独或相互组合确定的状况。植物健康状况的上述迹象可以相互依存或可以相互影响。
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。
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,特别是0.1-0.75kg/ha。
在植物繁殖材料如种子例如通过撒粉、包衣或浸润的处理中,通常要求每100kg植物繁殖材料(优选种子)0.1-1000g,优选1-1000g,更优选1-100g,最优选5-100g的活性物质量。
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、喷雾飞机或灌溉系统。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(也见“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(例如SC、OD、FS),可乳化浓缩物(例如EC),乳液(例如EW、EO、ES、ME),胶囊(例如CS、ZC),糊,锭剂,可湿性粉末或粉剂(例如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,New developments in crop protection product formulation,Agrow Reports DS243,T&F Informa,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。
合适的溶剂和液体载体是水和有机溶剂,如中到高沸点的矿物油馏分,例如煤油、柴油;植物或动物来源的油;脂族、环状和芳族烃类,例如甲苯、石蜡、四氢萘和烷基化萘;醇类,如乙醇、丙醇、丁醇、苄醇、环己醇;二醇类;DMSO;酮类,例如环己酮;酯类,例如乳酸酯、碳酸酯、脂肪酸酯、γ-丁内酯;脂肪酸;膦酸酯;胺类;酰胺类,例如N-甲基吡咯烷酮,脂肪酸二甲基酰胺;以及它们的混合物。
合适的固体载体或填料是矿土,例如硅酸盐、硅胶、滑石、高岭土、石灰石、石灰、白垩、粘土、白云石、硅藻土、膨润土、硫酸钙、硫酸镁、氧化镁;多糖,例如纤维素、淀粉;肥料,例如硫酸铵、磷酸铵、硝酸铵、脲类;植物来源的产品,例如谷粉、树皮粉、木粉和坚果壳粉,以及它们的混合物。
合适的表面活性剂是表面活性化合物,如阴离子、阳离子、非离子和两性表面活性剂,嵌段聚合物,聚电解质,以及它们的混合物。该类表面活性剂可以用作乳化剂、分散剂、加溶剂、润湿剂、渗透促进剂、保护性胶体或辅助剂。表面活性剂的实例列于McCutcheon’s,第1卷:Emulsifiers&Detergents,McCutcheon’s Directories,Glen Rock,USA,2008(International Ed.或North American Ed.)中。
合适的阴离子表面活性剂是磺酸、硫酸、磷酸、羧酸的碱金属、碱土金属或铵盐以及它们的混合物。磺酸盐的实例是烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、木素磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基酚的磺酸盐、烷氧基化芳基酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例是脂肪酸的硫酸盐、油的硫酸盐、乙氧基化烷基酚的硫酸盐、醇的硫酸盐、乙氧基化醇的硫酸盐或脂肪酸酯的硫酸盐。磷酸盐的实例是磷酸盐酯。羧酸盐的实例是烷基羧酸盐以及羧化醇或烷基酚乙氧基化物。
合适的非离子表面活性剂是烷氧基化物,N-取代的脂肪酸酰胺,胺氧化物,酯类,糖基表面活性剂,聚合物表面活性剂及其混合物。烷氧基化物的实例是诸如已经被1-50当量烷氧基化的醇、烷基酚、胺、酰胺、芳基酚、脂肪酸或脂肪酸酯的化合物。可以将氧化乙烯和/或氧化丙烯用于烷氧基化,优选氧化乙烯。N-取代的脂肪酸酰胺的实例是脂肪酸葡糖酰胺或脂肪酸链烷醇酰胺。酯类的实例是脂肪酸酯,甘油酯或甘油单酯。糖基表面活性剂的实例是脱水山梨醇、乙氧基化脱水山梨醇、蔗糖和葡萄糖酯或烷基聚葡糖苷。聚合物表面活性剂的实例是乙烯基吡咯烷酮、乙烯醇或乙酸乙烯酯的均聚物或共聚物。
合适的阳离子表面活性剂是季型表面活性剂,例如具有1或2个疏水性基团的季铵化合物,或长链伯胺的盐。合适的两性表面活性剂是烷基甜菜碱和咪唑啉类。合适的嵌段聚合物是包含聚氧乙烯和聚氧丙烯的嵌段的A-B或A-B-A类型嵌段聚合物,或包含链烷醇、聚氧乙烯和聚氧丙烯的嵌段的A-B-C类型嵌段聚合物。合适的聚电解质是聚酸或聚碱。聚酸的实例是聚丙烯酸的碱金属盐或聚酸梳状聚合物。聚碱的实例是聚乙烯基胺或聚乙烯胺。
合适的辅助剂是本身具有可忽略的农药活性或者本身甚至没有农药活性且改善化合物I对目标物的生物学性能的化合物。实例是表面活性剂,矿物油或植物油以及其他助剂。其他实例由Knowles,Adjuvants and additives,Agrow Reports DS256,T&F InformaUK,2006,第5章列出。
合适的增稠剂是多糖(例如黄原胶、羧甲基纤维素)、无机粘土(有机改性或未改性的)、聚羧酸盐和硅酸盐。
合适的杀菌剂是拌棉醇(bronopol)和异噻唑啉酮衍生物如烷基异噻唑啉酮类和苯并异噻唑啉酮类。
合适的防冻剂是乙二醇、丙二醇、尿素和甘油。
合适的消泡剂是聚硅氧烷、长链醇和脂肪酸盐。
合适的着色剂(例如着红色、蓝色或绿色)是低水溶性颜料和水溶性染料。实例是无机着色剂(例如氧化铁、氧化钛、六氰合铁酸铁)和有机着色剂(例如茜素着色剂、偶氮着色剂和酞菁着色剂)。
合适的增粘剂或粘合剂是聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇、聚丙烯酸酯、生物蜡或合成蜡以及纤维素醚。
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)。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%的至少一种辅助剂。活性物质(例如化合物I)以90-100%,优选95-100%的纯度(根据NMR波谱)使用。
为了处理植物繁殖材料,尤其是种子,通常使用种子处理用溶液(LS),悬浮乳液(SE),可流动浓缩物(FS),干处理用粉末(DS),淤浆处理用水分散性粉末(WS),水溶性粉末(SS),乳液(ES),可乳化浓缩物(EC)和凝胶(GF)。所述组合物在稀释2-10倍后在即用制剂中给出0.01-60重量%,优选0.1-40重量%的活性物质浓度。施用可以在播种之前或期间进行。化合物I及其组合物分别在植物繁殖材料,尤其是种子上的施用方法包括拌种、包衣、造粒、撒粉、浸泡以及犁沟内施用方法。优选通过不诱发萌发的方法,例如通过拌种、造粒、包衣和撒粉将化合物I或其组合物分别施用于植物繁殖材料上。
可以向化合物I或其组合物中作为预混物加入或者直到在紧临使用前加入(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。
农药通常为通过其效果将有害物阻止、失能、杀灭或在其他方面受挫的化学或生物药剂(如灭害活性成分、化合物、组合物、病毒、细菌、抗菌剂或消毒剂)。目标有害物可以包括破坏财产、引起麻烦、传播疾病或为疾病传病媒介的昆虫、植物病原体、杂草、软体动物、鸟类、哺乳动物、鱼类、线虫(蛔虫)和微生物。术语“农药”还包括改变植物的预期生长、开花或生殖率的植物生长调节剂;引起叶子或其他树叶从植物脱落的落叶剂,这通常促进收获;促进活体组织,如不希望的植物地上部分干燥的干燥剂;活化植物生理机能以防御某些有害物的植物活化剂;降低农药对农作物的不希望除草作用的安全剂;以及影响植物生理机能例如以增强植物生长、生物质、产量或农作物的可收获物品的任何其他质量参数的植物生长促进剂。
已经将生物农药定义为基于微生物(细菌、真菌、病毒、线虫等)或天然产物(化合物,如来自生物或其他天然来源的代谢物、蛋白质或提取物)的农药形式(U.S.Environmental Protection Agency:http://www.epa.gov/pesticides/biopesticides/)。生物农药落入两个主要类别,即微生物农药和生物化学农药中:
(1)微生物农药由细菌、真菌或病毒构成(并且通常包括细菌和真菌产生的代谢物)。昆虫病原线虫也被分类为微生物农药,尽管它们是多细胞的。
(2)生物化学农药是防治有害物或提供如下所定义的其他作物保护用途,但对哺乳动物相对无毒的天然物质。
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(azoxystrobin)(A.1.1)、甲香菌酯(coumethoxystrobin)(A.1.2)、丁香菌酯(coumoxystrobin)(A.1.3)、醚菌胺(dimoxystrobin)(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(metominostrobin)(A.1.11)、肟醚菌胺(orysastrobin)(A.1.12)、啶氧菌酯(picoxystrobin)(A.1.13)、唑菌胺酯(pyraclostrobin)(A.1.14)、唑胺菌酯(pyrametostrobin)(A.1.15)、唑菌酯(pyraoxystrobin)(A.1.16)、肟菌酯(trifloxystrobin)(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)、吡菌苯威(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)、metyltetrapole(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)、异丙噻菌胺(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)、三氟吡啶胺(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:三唑类:戊环唑(azaconazole)(B.1.1)、双苯三唑醇(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)、/>咪唑(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)、三唑酮(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)、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈(B.1.33)、伊芬三氟康唑(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-(1,2,4-三唑-1-基)丙-2-醇、(2S)-2-[4-(4-氯苯氧基)-2-三氟甲基苯基]-1-(1,2,4-三唑-1-基)丙-2-醇、2-(氯甲基)-2-甲基-5-(对甲苯基甲基)-1-(1,2,4-三唑-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-(1,2,4-三唑-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-(1,2,4-三唑-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-(1,2,4-三唑-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)、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)细胞分裂和细胞骨架抑制剂
-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);
-其他细胞分裂抑制剂: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)、苯啶菌酮(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(kasugamycinhydrochloride-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)、霜霉灭(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(polyoxinB)(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)、磺菌胺(flusulfamide)(K.1.15)、氟噻唑菌腈(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)、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(benziothiazolinone)(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)、N-(2-氟苯基)-4-[5-三氟甲基-1,2,4-/>二唑-3-基]苯甲酰胺(K.1.58)、N-甲基-4-[5-三氟甲基-1,2,4-/>二唑-3-基]硫代苯甲酰胺(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);
L)生物农药
L1)具有杀真菌、杀细菌、杀病毒和/或植物防御活化剂活性的微生物农药:白粉寄生孢(Ampelomyces quisqualis),黄曲霉(Aspergillus flavus),出芽短梗霉(Aureobasidium pullulans),高地芽孢杆菌(Bacillusaltitudinis),解淀粉芽孢杆菌(B.amyloliquefaciens),解淀粉芽孢杆菌植物亚种(B.amyloliquefaciensssp.plantarum)(也称为贝莱斯芽孢杆菌(B.velezensis),巨大芽孢杆菌(B.megaterium),莫海威芽孢杆菌(B.mojavensis),蕈状芽孢杆菌(B.mycoides),短小芽孢杆菌(B.pumilus),简单芽孢杆菌(B.simplex),盐土芽孢杆菌(B.solisalsi),枯草芽孢杆菌(B.
subtilis),解淀粉枯草芽孢杆菌变种(B.subtilis var.amyloliquefaciens),贝莱斯芽孢杆菌,橄榄假丝酵母(Candida oleophila),拮抗酵母(C.
saitoana),番茄细菌性溃疡病(Clavibacter michiganensis)(噬菌体),盾壳霉(Coniothyrium minitans),寄生隐丛赤壳菌(Cryphonectriaparasitica),白色隐球菌(Cryptococcus albidus),看麦娘双极毛孢(Dilophosphora alopecuri),尖镰孢(Fusarium oxysporum),粉红螺旋聚孢霉(Clonostachys rosea f.catenulate)(也称为链孢粘帚菌(Gliocladiumcatenulatum)),粉红粘帚霉(Gliocladium roseum),抗生素溶杆菌(Lysobacter antibioticus),产霉溶杆菌(L.enzymogenes),核果梅奇酵母(Metschnikowia fructicola),Microdochium dimerum,小球壳孢(Microsphaeropsisochracea),白色产气霉(Muscodor albus),蜂房芽孢杆菌(Paenibacillus alvei),Paenibacillus epiphyticus,多粘类芽孢杆菌(P.
polymyxa),成团泛菌(Pantoea vagans),比莱青霉(Penicillium bilaiae),大伏革菌(Phlebiopsis gigantea),假单胞菌属(Pseudomonas sp.),绿镇假单胞菌(Pseudomonas chloraphis),Pseudozyma flocculosa,异常毕赤酵母(Pichia anomala),寡雄腐霉(Pythium oligandrum),Sphaerodesmycoparasitica,灰绿链霉菌(Streptomycesgriseoviridis),利迪链霉菌(S.lydicus),紫黑链霉菌(S.violaceusniger),黄蓝状菌(Talaromycesflavus),Trichoderma asperelloides,棘孢木霉(T.asperellum),深绿木霉(T.atroviride),顶孢木霉(T.fertile),盖姆斯木霉(T.gamsii),钩状木霉(T.harmatum),哈茨木霉(T.harzianum),多孔木霉(T.polysporum),钩木霉(T.stromaticum),绿木霉(T.virens),绿色木霉(T.viride),透根核瑚菌(Typhula phacorrhiza),奥德曼细基格孢(Ulocladiumoudemansii),大丽轮枝菌(Verticillium dahlia),小西葫芦黄花叶病毒(无毒菌株);
L2)具有杀真菌、杀细菌、杀病毒和/或植物防御活化剂活性的生物化学农药:超敏蛋白,大虎杖(Reynoutria sachalinensis)提取物;
L3)具有杀虫、杀螨、杀螺和/或杀线虫活性的微生物农药:放射形土壤杆菌(Agrobacterium radiobacter),蜡样芽孢杆菌(Bacillus cereus),坚强芽孢杆菌(B.firmus),苏云金芽孢杆菌(B.thuringiensis),苏云金芽孢杆菌鲇泽亚种(B.thuringiensis ssp.aizawai),苏云金芽孢杆菌以色列亚种(B.t.ssp.israelensis),苏云金芽孢杆菌蜡螟亚种(B.t.ssp.galleriae),苏云金芽孢杆菌库斯塔克亚种(B.t.ssp.kurstaki),苏云金芽孢杆菌拟步行甲亚种(B.t.ssp.tenebrionis),球孢白僵菌(Beauveria bassiana),布氏白僵菌(B.brongniartii),伯克霍尔德氏菌(Burkholderiaspp.),枯草色素杆菌(Chromobacterium subtsugae),苹果蠹蛾颗粒体病毒(Cydiapomonella granulovirus)(CpGV),伪苹果蠹蛾颗粒体病毒(Cryptophlebialeucotreta granulovirus)(CrleGV),黄杆菌属(Flavobacterium spp.),棉铃虫核型多角体病毒(Helicoverpa armigeranucleopolyhedrovirus)(HearNPV),棉铃虫核型多角体病毒(Helicoverpazea nucleopolyhedrovirus)(HzNPV),棉铃虫单壳核型多角体病毒(Helicoverpa zea single capsid nucleopolyhedrovirus)(HzSNPV),嗜菌异小杆线虫(Heterorhabditis bacteriophora),玫烟色棒束孢(Isariafumosorosea),长孢蜡蚧菌(Lecanicillium longisporum),蝇蚧疥霉(L.muscarium),金龟子绿僵菌(Metarhiziumanisopliae),金龟子绿僵菌变种(M.anisopliae var.anisopliae),金龟子绿僵菌蝗变种(M.anisopliaevar.acridum),莱氏野村菌(Nomuraea rileyi),玫烟色拟青霉(Paecilomyces fumosoroseus),淡紫色拟青霉(P.lilacinus),日本甲虫类芽孢杆菌(Paenibacillus popilliae),巴氏杆菌属(Pasteuria spp.),拟斯扎瓦巴氏杆菌(P.nishizawae),穿刺巴氏杆菌(P.penetrans),分枝巴氏杆菌(P.ramosa),李氏巴氏杆菌(P.thornea),P.usgae,荧光假单胞菌(Pseudomonas fluorescens),灰翅夜蛾核型多角体病毒(Spodopteralittoralis nucleopolyhedrovirus)(SpliNPV),斯氏小卷蛾线虫(Steinernema carpocapsae),斯氏夜蛾线虫(S.feltiae),锯蜂线虫(S.kraussei),鲜黄链霉菌(Streptomyces galbus),细黄链霉菌(S.microflavus);
L4)具有杀虫、杀螨、杀螺、信息素和/或杀线虫活性的生物化学农药:L-香芹酮、柠檬醛、乙酸(E,Z)-7,9-十二碳二烯-1-基酯、甲酸乙酯、(E,Z)-2,4-癸二烯酸乙酯(梨酯)、(Z,Z,E)-7,11,13-十六碳三烯醛、丁酸庚酯、肉豆蔻酸异丙酯、千里酸熏衣草酯、顺式-茉莉酮、2-甲基-1-丁醇、甲基丁香酚、茉莉酮酸甲酯、(E,Z)-2,13-十八碳二烯-1-醇、(E,Z)-2,13-十八碳二烯-1-醇乙酸酯、(E,Z)-3,13-十八碳二烯-1-醇、R-1-辛烯-3-醇、白蚁信息素(pentatermanone)、乙酸(E,Z,Z)-3,8,11-十四碳三烯基酯、乙酸(Z,E)-9,12-十四碳二烯-1-基酯、Z-7-十四碳烯-2-酮、乙酸Z-9-十四碳烯-1-基酯、Z-11-十四碳烯醛、Z-11-十四碳烯-1-醇、土荆芥(Chenopodiumambrosiodes)提取物、印度楝树油、皂树(Quillay)提取物;
L5)具有植物逆境降低、植物生长调节剂、植物生长促进和/或产量提高活性的微生物农药:无乳固氮螺菌(Azospirillum amazonense),巴西固氮螺菌(A.brasilense),生脂固氮螺菌(A.lipoferum),伊拉克固氮螺菌(A.irakense),高盐固氮螺菌(A.halopraeferens),慢生根瘤菌属(Bradyrhizobium spp.),埃氏慢生根瘤菌(B.elkanii),日本慢生根瘤菌(B.japonicum),辽宁慢生根瘤菌(B.liaoningense),慢生羽扇豆根瘤菌(B.lupini),食酸戴尔福特菌(Delftia acidovorans),丛枝菌根真菌(Glomusintraradices),中生根瘤菌属(Mesorhizobium spp.),豌豆根瘤菌菜豆生物型(Rhizobiumleguminosarum bv.phaseoli),豌豆根瘤菌三叶草生物型(R.l.bv.trifolii),豌豆根瘤菌蚕豆生物型(R.l.bv.viciae),热带根瘤菌(R.tropici),苜蓿根瘤菌(Sinorhizobiummeliloti);
O)选自O.1-O.29类的杀虫剂
O.1乙酰胆碱酯酶(AChE)抑制剂:涕灭威(aldicarb)、棉铃威(alanycarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮氧威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、苯虫威(ethiofencarb)、仲丁威(fenobucarb)、抗螨脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、混杀威(trimethacarb)、XMC、灭杀威(xylylcarb)、唑蚜威(triazamate)、高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphosmethyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、丙线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑硫磷(fosthiazate)、庚烯磷(heptenophos)、新烟碱类(imicyafos)、异丙胺磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯、异/>唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、一六零五(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、巴胺磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫威(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭磷(vamidothion);
O.2GABA门控氯离子通道拮抗剂:硫丹(endosulfan)、氯丹(chlordane)、乙虫腈(ethiprole)、锐劲特(fipronil)、丁烯氟虫腈(flufiprole)、pyrafluprole、pyriprole;
O.3钠通道调节剂:氟丙菊酯(acrinathrin)、丙烯除虫菊(allethrin)、右旋丙烯菊酯(d-cis-trans allethrin)、右旋反式丙烯菊酯(d-trans allethrin)、氟氯菊酯(bifenthrin)、kappa-bifenthrin、生物烯丙菊酯(bioallethrin)、2-环戊烯基生物烯丙菊酯(bioallethrin S-cyclopentenyl)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、氯氟氰菊酯(lambda-cyhalothrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、高效反式氯氰菊酯(theta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(tau-fluvalinate)、溴氟醚菊酯(halfenprox)、heptafluthrin、咪炔菊酯(imiprothrin)、氯氟醚菊酯(meperfluthrin)、甲氧苄氟菊酯(metofluthrin)、momfluorothrin、epsilon-momfluorothrin、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、除虫菊酯(pyrethrin(除虫菊(pyrethrum)))、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、kappa-tefluthrin、四氟醚菊酯(tetramethylfluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、DDT、甲氧滴滴涕(methoxychlor);
O.4烟碱型乙酰胆碱受体激动剂(nAChR):吡虫清(acetamiprid)、噻虫胺(clothianidin)、环氧虫啶(cycloxaprid)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、硝胺烯啶(nitenpyram)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、4,5-二氢-N-硝基-1-(2-环氧乙烷基甲基)-1H-咪唑-2-胺、(2E-)-1-[(6-氯吡啶-3-基)甲基]-N'-硝基-2-亚戊基氨基胍、1-[(6-氯吡啶-3-基)甲基]-7-甲基-8-硝基-5-丙氧基-1,2,3,5,6,7-六氢咪唑并[1,2-a]吡啶、烟碱(nicotine)、氟啶虫胺腈(sulfoxaflor)、flupyradifurone、三氟苯嘧啶(triflumezopyrim)、(3R)-3-(2-氯噻唑-5-基)-8-甲基-5-氧代-6-苯基-2,3-二氢噻唑并[3,2-a]嘧啶-8--7-醇盐、(3S)-3-(6-氯-3-吡啶基)-8-甲基-5-氧代-6-苯基-2,3-二氢噻唑并[3,2-a]嘧啶-8-/>-7-醇盐、(3S)-8-甲基-5-氧代-6-苯基-3-嘧啶-5-基-2,3-二氢噻唑并[3,2-a]嘧啶-8-/>-7-醇盐、(3R)-3-(2-氯噻唑-5-基)-8-甲基-5-氧代-6-[3-三氟甲基苯基]-2,3-二氢噻唑并[3,2-a]嘧啶-8-/>-7-醇盐、(3R)-3-(2-氯噻唑-5-基)-6-(3,5-二氯苯基)-8-甲基-5-氧代-2,3-二氢噻唑并[3,2-a]嘧啶-8-/>-7-醇盐、(3R)-3-(2-氯噻唑-5-基)-8-乙基-5-氧代-6-苯基-2,3-二氢噻唑并[3,2-a]嘧啶-8-/>-7-醇盐;
O.5烟碱型乙酰胆碱受体变构活化剂:艾克敌105(spinosad)、乙基多杀菌素(spinetoram);
O.6氯离子通道活化剂:齐墩螨素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、伊维菌素(ivermectin)、雷皮菌素(lepimectin)、米尔螨素(milbemectin);
O.7保幼激素模拟物:蒙512(hydroprene)、烯虫炔酯(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb)、蚊蝇醚(pyriproxyfen);
O.8其他非特异性(多位点)抑制剂:溴甲烷和其他烷基卤化物、氯化苦(chloropicrin)、磺酰氟(sulfuryl fluoride)、硼砂、酒石酸氧锑钾(tartaremetic);
O.9弦音器官TRPV通道调节剂:拒嗪酮(pymetrozine);pyrifluquinazon;
O.10螨虫生长抑制剂:四螨嗪(clofentezine)、噻螨酮(hexythiazox)、氟螨嗪(diflovidazin)、特苯唑(etoxazole);
O.11昆虫中肠膜的微生物干扰剂:苏云金芽孢杆菌(Bacillusthuringiensis)、球形芽孢杆菌(Bacillus sphaericus)以及它们产生的杀虫蛋白:苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis subsp.israelensis)、球形芽孢杆菌、苏云金芽胞杆菌鲇泽亚种(Bacillusthuringiensis subsp.aizawai)、苏云金芽胞杆菌库斯塔克亚种(Bacillusthuringiensis subsp.kurstaki)、苏云金芽胞杆菌拟步行甲亚种(Bacillusthuringiensis subsp.tenebrionis),Bt作物蛋白:Cry1Ab,Cry1Ac,Cry1Fa,Cry2Ab,mCry3A,Cry3Ab,Cry3Bb,Cry34/35Ab1;
O.12线粒体ATP合成酶抑制剂:杀螨硫隆(diafenthiuron)、三唑锡(azocyclotin)、三环锡(cyhexatin)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
O.13经由质子梯度干扰的氧化磷酸化去偶剂:氟唑虫清(chlorfenapyr)、二硝酚(DNOC)、氟虫胺(sulfluramid);
O.14烟碱型乙酰胆碱受体(nAChR)通道阻断剂:杀虫磺(bensultap)、杀螟丹(cartap hydrochloride)、杀虫环(thiocyclam)、杀虫双(thiosultapsodium);
O.15类型0几丁质生物合成抑制剂:双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟虫酰脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);
O.16类型1几丁质生物合成抑制剂:噻嗪酮(buprofezin);
O.17蜕皮干扰剂:灭蝇胺(cyromazine);
O.18蜕皮素受体激动剂:甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、特丁苯酰肼(halofenozide)、呋喃虫酰肼(fufenozide)、环虫酰肼(chromafenozide);
O.19章鱼胺受体激动剂(Octopamin receptor agonsit):双甲脒(amitraz);
O.20线粒体配合物III电子传输抑制剂:灭蚁腙(hydramethylnon)、灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)、联苯肼酯(bifenazate);
O.21线粒体配合物I电子传输抑制剂:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、鱼藤酮(rotenone);
O.22电压依赖性钠通道阻断剂:二唑虫(indoxacarb)、氰氟虫胺(metaflumizone)、2-[2-(4-氰基苯基)-1-[3-三氟甲基苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]氨基脲、N-(3-氯-2-甲基苯基)-2-[(4-氯苯基)[4-[甲基(甲基磺酰基)氨基]苯基]亚甲基]氨基脲;
O.23乙酰CoA羧化酶抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、spiropidion;
O.24线粒体配合物IV电子传输抑制剂:磷化铝、磷化钙、膦、磷化锌、氰化物;
O.25线粒体配合物II电子传输抑制剂:腈吡螨酯(cyenopyrafen)、丁氟螨酯(cyflumetofen);
O.26鱼尼汀(Ryanodine)受体调节剂:氟虫酰胺(flubendiamide)、氯虫酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)、环溴虫酰胺(cyclaniliprole)、氟氰虫酰胺(tetraniliprole)、(R)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-三氟甲基乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺、(S)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-三氟甲基乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺、2-[3,5-二溴-2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)苯甲酰基]-1,2-二甲基肼甲酸甲酯、N-[4,6-二氯-2-[(二乙基-λ-4-亚硫烷基(sulfanylidene))氨基甲酰基]苯基]-2-(3-氯-2-吡啶基)-5-三氟甲基吡唑-3-甲酰胺、N-[4-氯-2-[(二乙基-λ-4-亚硫烷基)氨基甲酰基]-6-甲基苯基]-2-(3-氯-2-吡啶基)-5-三氟甲基吡唑-3-甲酰胺、N-[4-氯-2-[(二-2-丙基-λ-4-亚硫烷基)氨基甲酰基]-6-甲基苯基]-2-(3-氯-2-吡啶基)-5-三氟甲基吡唑-3-甲酰胺、N-[4,6-二氯-2-[(二-2-丙基-λ-4-亚硫烷基)氨基甲酰基]苯基]-2-(3-氯-2-吡啶基)-5-三氟甲基吡唑-3-甲酰胺、N-[4,6-二溴-2-[(二乙基-λ-4-亚硫烷基)氨基甲酰基]苯基]-2-(3-氯-2-吡啶基)-5-三氟甲基吡唑-3-甲酰胺、N-[2-(5-氨基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺、3-氯-1-(3-氯-2-吡啶基)-N-[2,4-二氯-6-[[(1-氰基-1-甲基乙基)氨基]羰基]苯基]-1H-吡唑-5-甲酰胺、四氯虫酰胺(tetrachlorantraniliprole)、N-[4-氯-2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-氟甲氧基-1H-吡唑-5-甲酰胺、氯氟氰虫酰胺(cyhalodiamide);
O.27:弦音器官调节剂—未限定的目标位点:氟啶虫酰胺(flonicamid);
O.28.未知或不确定作用模式的杀虫活性化合物:双丙环虫酯(afidopyropen)、afoxolaner、印楝素(azadirachtin)、磺胺螨酯(amidoflumet)、苯螨特(benzoximate)、broflanilide、溴螨酯(bromopropylate)、喹菌酮(chinomethionat)、冰晶石(cryolite)、环丙氟虫胺(cyproflanilide)、dicloromezotiaz、三氯杀螨醇(dicofol)、嘧虫胺(flufenerim)、flometoquin、氟噻虫砜(fluensulfone)、fluhexafon、氟吡菌酰胺(fluopyram)、fluralaner、虫酮(metoxadiazone)、增效醚(piperonyl butoxide)、pyflubumide、啶虫丙醚(pyridalyl)、tioxazafen、11-(4-氯-2,6-二甲基苯基)-12-羟基-1,4-二氧杂-9-氮杂二螺[4.2.4.2]十四碳-11-烯-10-酮、3-(4’-氟-2,4-二甲基联苯-3-基)-4-羟基-8-氧杂-1-氮杂螺[4.5]癸-3-烯-2-酮、1-[2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基]-3-三氟甲基-1H-1,2,4-三唑-5-胺、坚强芽孢杆菌(Bacillus firmus)I-1582、flupyrimin、三氟咪啶酰胺(fluazaindolizine)、4-[5-(3,5-二氯苯基)-5-三氟甲基-4H-异/>唑-3-基]-2-甲基-N-(1-氧代硫杂丁环-3-基)苯甲酰胺、fluxametamide、5-[3-[2,6-二氯-4-(3,3-二氯烯丙氧基)苯氧基]丙氧基]-1H-吡唑、4-氰基-N-[2-氰基-5-[[2,6-二溴-4-[1,2,2,3,3,3-六氟-1-三氟甲基丙基]苯基]氨基甲酰基]苯基]-2-甲基苯甲酰胺、4-氰基-3-[(4-氰基-2-甲基苯甲酰基)氨基]-N-[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-三氟甲基丙基]苯基]-2-氟苯甲酰胺、N-[5-[[2-氯-6-氰基-4-[1,2,2,3,3,3-六氟-1-三氟甲基丙基]苯基]氨基甲酰基]-2-氰基苯基]-4-氰基-2-甲基苯甲酰胺、N-[5-[[2-溴-6-氯-4-[2,2,2-三氟-1-羟基-1-三氟甲基乙基]苯基]氨基甲酰基]-2-氰基苯基]-4-氰基-2-甲基苯甲酰胺、N-[5-[[2-溴-6-氯-4-[1,2,2,3,3,3-六氟-1-三氟甲基丙基]苯基]氨基甲酰基]-2-氰基苯基]-4-氰基-2-甲基苯甲酰胺)、4-氰基-N-[2-氰基-5-[[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-三氟甲基丙基]苯基]氨基甲酰基]苯基]-2-甲基苯甲酰胺、4-氰基-N-[2-氰基-5-[[2,6-二氯-4-[1,2,2,2-四氟-1-三氟甲基乙基]苯基]氨基甲酰基]苯基]-2-甲基苯甲酰胺、N-[5-[[2-溴-6-氯-4-[1,2,2,2-四氟-1-三氟甲基乙基]苯基]氨基甲酰基]-2-氰基苯基]-4-氰基-2-甲基苯甲酰胺、2-(1,3-二/>烷-2-基)-6-[2-(3-吡啶基)-5-噻唑基]吡啶、2-[6-[2-(5-氟-3-吡啶基)-5-噻唑基]-2-吡啶基]嘧啶、2-[6-[2-(3-吡啶基)-5-噻唑基]-2-吡啶基]嘧啶、N-甲基磺酰基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-甲酰胺、N-甲基磺酰基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-甲酰胺、1-[(6-氯-3-吡啶基)甲基]-1,2,3,5,6,7-六氢-5-甲氧基-7-甲基-8-硝基咪唑并[1,2-a]吡啶、1-[(6-氯吡啶-3-基)甲基]-7-甲基-8-硝基-1,2,3,5,6,7-六氢咪唑并[1,2-a]吡啶-5-醇、1-异丙基-N,5-二甲基-N-哒嗪-4-基吡唑-4-甲酰胺、1-(1,2-二甲基丙基)-N-乙基-5-甲基-N-哒嗪-4-基吡唑-4-甲酰胺、N,5-二甲基-N-哒嗪-4-基-1-(2,2,2-三氟-1-甲基乙基)吡唑-4-甲酰胺、1-[1-(1-氰基环丙基)乙基]-N-乙基-5-甲基-N-哒嗪-4-基吡唑-4-甲酰胺、N-乙基-1-(2-氟-1-甲基丙基)-5-甲基-N-哒嗪-4-基吡唑-4-甲酰胺、1-(1,2-二甲基丙基)-N,5-二甲基-N-哒嗪-4-基吡唑-4-甲酰胺、1-[1-(1-氰基环丙基)乙基]-N,5-二甲基-N-哒嗪-4-基吡唑-4-甲酰胺、N-甲基-1-(2-氟-1-甲基丙基]-5-甲基-N-哒嗪-4-基吡唑-4-甲酰胺、1-(4,4-二氟环己基)-N-乙基-5-甲基-N-哒嗪-4-基吡唑-4-甲酰胺、1-(4,4-二氟环己基)-N,5-二甲基-N-哒嗪-4-基吡唑-4-甲酰胺、N-(1-甲基乙基)-2-(3-吡啶基)-2H-吲唑-4-甲酰胺、N-环丙基-2-(3-吡啶基)-2H-吲唑-4-甲酰胺、N-环己基-2-(3-吡啶基)-2H-吲唑-4-甲酰胺、2-(3-吡啶基)-N-(2,2,2-三氟乙基)-2H-吲唑-4-甲酰胺、2-(3-吡啶基)-N-[(四氢-2-呋喃基)甲基]-2H-吲唑-5-甲酰胺、2-[[2-(3-吡啶基)-2H-吲唑-5-基]羰基]肼甲酸甲酯、N-[(2,2-二氟环丙基)甲基]-2-(3-吡啶基)-2H-吲唑-5-甲酰胺、N-(2,2-二氟丙基)-2-(3-吡啶基)-2H-吲唑-5-甲酰胺、2-(3-吡啶基)-N-(2-嘧啶基甲基)-2H-吲唑-5-甲酰胺、N-[(5-甲基-2-吡嗪基)甲基]-2-(3-吡啶基)-2H-吲唑-5-甲酰胺、tyclopyrazoflor、sarolaner、lotilaner、N-[4-氯-3-[[(苯基甲基)氨基]羰基]苯基]-1-甲基-3-(1,1,2,2,2-五氟乙基)-4-三氟甲基-1H-吡唑-5-甲酰胺、2-(3-乙基磺酰基-2-吡啶基)-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-[3-乙基磺酰基-5-三氟甲基-2-吡啶基]-3-甲基-6-三氟甲基-咪唑并[4,5-b]吡啶、异/>唑虫酰胺(isocycloseram)、N-[4-氯-3-(环丙基氨基甲酰基)苯基]-2-甲基-5-(1,1,2,2,2-五氟乙基)-4-三氟甲基吡唑-3-甲酰胺、N-[4-氯-3-[(1-氰基环丙基)氨基甲酰基]苯基]-2-甲基-5-(1,1,2,2,2-五氟乙基)-4-三氟甲基吡唑-3-甲酰胺、acynonapyr、benzpyrimoxan、tigolaner、氯-N-(1-氰基环丙基)-5-[1-[2-甲基-5-(1,1,2,2,2-五氟乙基)-4-三氟甲基吡唑-3-基]吡唑-4-基]苯甲酰胺、oxazosulfyl、N-[4-[1-[4-三氟甲氧基苯基]-1,2,4-三唑-3-基]苯基]氨基甲酸[(2S,3R,4R,5S,6S)-3,5-二甲氧基-6-甲基-4-丙氧基四氢吡喃-2-基]酯、N-[4-[1-[4-三氟甲氧基苯基]-1,2,4-三唑-3-基]苯基]氨基甲酸[(2S,3R,4R,5S,6S)-3,4,5-三甲氧基-6-甲基四氢吡喃-2-基]酯、N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1,2,4-三唑-3-基]苯基]氨基甲酸[(2S,3R,4R,5S,6S)-3,5-二甲氧基-6-甲基-4-丙氧基四氢吡喃-2-基]酯、N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1,2,4-三唑-3-基]苯基]氨基甲酸[(2S,3R,4R,5S,6S)-3,4,5-三甲氧基-6-甲基四氢吡喃-2-基]酯、(2Z)-3-(2-异丙基苯基)-2-[(E)-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1,2,4-三唑-3-基]苯基]亚甲基亚肼基]噻唑烷-4-酮、2-(6-氯-3-乙基磺酰基咪唑并[1,2-a]吡啶-2-基)-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-(6-溴-3-乙基磺酰基咪唑并[1,2-a]吡啶-2-基)-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-(3-乙基磺酰基-6-碘咪唑并[1,2-a]吡啶-2-基)-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-[3-乙基磺酰基-6-三氟甲基咪唑并[1,2-a]
吡啶-2-基]-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-(7-氯-3-乙基磺酰基咪唑并[1,2-a]吡啶-2-基)-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-(3-乙基磺酰基-7-碘咪唑并[1,2-a]吡啶-2-基)-3-甲基-6-三氟甲基咪唑并[4,5-b]
吡啶、3-乙基磺酰基-6-碘-2-[3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶-2-基]
咪唑并[1,2-a]吡啶-8-甲腈、2-[3-乙基磺酰基-8-氟-6-三氟甲基咪唑并[1,2-a]吡啶-2-基]-3-甲基-6-三氟甲基咪唑并[4,5-b]吡啶、2-[3-乙基磺酰基-7-三氟甲基咪唑并[1,2-a]吡啶-2-基]-3-甲基-6-(三氟甲基亚磺酰基)咪唑并[4,5-b]吡啶、2-[3-乙基磺酰基-7-三氟甲基咪唑并[1,2-a]吡啶-2-基]-3-甲基-6-三氟甲基咪唑并[4,5-c]吡啶、2-(6-溴-3-乙基磺酰基咪唑并[1,2-a]吡啶-2-基)-6-三氟甲基吡唑并[4,3-c]吡啶。
称为组分2的活性物质、其制备及其例如对有害真菌的活性是已知的(参见http://www.alanwood.net/pesticides/);这些物质可以市购。由IUPAC命名法描述的化合物、其制备及其农药活性也是已知的(参见Can.J.Plant Sci.48(6),587-94,1968;EP-A141 317;EP-A 152 031;EP-A 226 917;EP-A 243 970;EP-A 256 503;EP-A 428 941;EP-A532 022;EP-A 1 028125;EP-A 1 035 122;EP-A 1 201 648;EP-A 1 122 244,JP2002316902;DE 19650197;DE 10021412;DE 102005009458;US 3,296,272;US 3,325,503;WO 98/46608;WO 99/14187;WO 99/24413;WO 99/27783;WO 00/29404;WO 00/46148;WO00/65913;WO 01/54501;WO 01/56358;WO 02/22583;WO 02/40431;WO 03/10149;WO 03/11853;WO 03/14103;WO 03/16286;WO 03/53145;WO 03/61388;WO 03/66609;WO 03/74491;WO 04/49804;WO 04/83193;WO 05/120234;WO 05/123689;WO 05/123690;WO 05/63721;WO 05/87772;WO 05/87773;WO 06/15866;WO 06/87325;WO 06/87343;WO 07/82098;WO 07/90624,WO 10/139271,WO 11/028657,WO 12/168188,WO 07/006670,WO 11/77514;WO 13/047749,WO 10/069882,WO 13/047441,WO 03/16303,WO 09/90181,WO 13/007767,WO 13/010862,WO 13/127704,WO 13/024009,WO 13/24010,WO 13/047441,WO 13/162072,WO 13/092224,WO 11/135833,CN 1907024,CN 1456054,CN 103387541,CN1309897,WO 12/84812,CN 1907024,WO 09094442,WO 14/60177,WO 13/116251,WO 08/013622,WO 15/65922,WO 94/01546,EP 2865265,WO 07/129454,WO 12/165511,WO 11/081174,WO 13/47441,WO 16/156241,WO 16/162265)。一些化合物由其CAS登记号识别,该登记号由连字符分成三部分,第一部分由2-7位数构成,第二部分由2位数构成并且第三部分由一位数构成。
根据本发明,生物农药(油如印度楝树油除外)的固体物质(干物质)被认为是活性组分(例如在微生物农药的液体配制剂情况下在干燥或蒸发提取或悬浮介质之后得到)。对于生物提取物如皂树提取物所用重量比和百分数基于相应提取物的干物质(固体物质)的总重量。
以包括休眠形式的活微生物细胞形式包含至少一种微生物农药的组合物的总重量比可以使用相应微生物的CFU量来用下列等式计算相应活性组分的总重量而测定:1×1010CFU等于1g相应活性组分的总重量。菌落形成单位是活微生物细胞的度量。此外,CFU在线虫生物农药,如斯氏夜蛾线虫(Steinernema feltiae)情况下也可以理解为单个线虫(幼虫)的数目。
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,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范围内。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,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范围内。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,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范围内。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,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范围内。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,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范围内。
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,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范围内,并且组分1)和组分3)的重量比通常在1:100-100:1,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范围内。需要的话,将任何其他活性组分以20:1-1:20的比率加入组分1)中。这些比率也适合通过种子处理施用的混合物。
当将包含微生物农药的混合物用于作物保护中时,施用率为1×106-5×1016(或更大)CFU/ha,优选1×108-1×1013CFU/ha,甚至更优选1×109-5×1015CFU/ha,尤其是1×1012-5×1014CFU/ha。在线虫作为微生物农药(例如斯氏夜蛾线虫)的情况下,施用率通常为1×105-1×1012(或更大),优选1×108-1×1011,更优选5×108-1×1010个个体(例如呈卵、幼虫或任何其他活体阶段形式,优选非繁殖性(infetive)幼虫阶段)/ha。
当将包含微生物农药的混合物用于种子处理时,施用率通常为1×106-1×1012(或更大)CFU/种子,优选1×106-1×109CFU/种子。此外,就种子处理而言施用率通常为1×107-1×1014(或更大)CFU/100kg种子,优选1×109-约1×1012CFU/100kg种子。
优选包含至少一种选自A)组中的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)组中的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)组中的配合物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)组中的其他呼吸抑制剂,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)组中的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.1.34)、(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)组中的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)组中的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)组中的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。
选自L1)和/或L2)组的生物农药也可以具有杀虫、杀螨、杀螺、信息素、杀线虫、植物逆境降低、植物生长调节剂、植物生长促进和/或产量提高活性。选自L3)和/或L4)组的生物农药也可以具有杀真菌、杀细菌、杀病毒、植物防御活化剂、植物逆境降低、植物生长调节剂、植物生长促进和/或产量提高活性。选自L5)组的生物农药也可以具有杀真菌、杀细菌、杀病毒、植物防御活化剂、杀虫、杀螨、杀螺、信息素和/或杀线虫活性。
微生物农药,尤其是选自L1)、L3)和L5)组的那些不仅包括如本文所定义的相应微生物的分离的、纯培养物,而且包括其无细胞提取液、其在全汤培养物中的悬浮液以及含代谢物的培养基或由该微生物的全汤培养物得到的提纯代谢物。
这些生物农药中的许多已经保藏在本文所述的保藏号下(前缀如ATCC或DSM是指相应菌种保藏的首字母缩写,详情例如在这里见http://www.wfcc.info/ccinfo/ collection/by_acronym/),在文献中提到,被注册和/或可市购:在德国Konstanz于1989年分离的出芽短梗霉DSM 14940和DSM 14941的混合物(例如芽生孢子,来自奥地利bio-fermGmbH的Blossom),最初在巴西南部(Passo Fundo)小麦产区至少在1980年以前分离的巴西固氮螺菌(Azospirillum brasilense)Sp245(BR 11005;例如来自巴西BASFAgricultural Specialties Ltd.的/>Gramíneas),巴西固氮螺菌菌株Ab-V5和Ab-V6(例如来自Novozymes BioAg Produtos papra Agricultura Ltda.,QuattroBarras,巴西的AzoMax或来自巴西Simbiose-Agro的Simbiose-/>Plant Soil 331,413-425,2010),解淀粉芽孢杆菌(Bacillus amyloliquefaciens)菌株AP-188(NRRL B-50615和B-50331;US 8,445,255);解淀粉芽孢杆菌植物亚种菌株,以前有时也称为枯草芽孢杆菌,目前与甲基营养型芽孢杆菌(B.methylotrophicus)和贝莱斯芽孢杆菌一起分类为贝莱斯芽孢杆菌(Int.J.Syst.Evol.Microbiol.66,1212-1217,2016):在日本Kikugawa-shi由空气分离的解淀粉芽孢杆菌植物亚种(B.a.ssp.plantarum)或贝莱斯芽孢杆菌D747(US 20130236522 A1;FERM BP-8234;例如来自Certis LLC,USA的Double NickelTM55WDG),在德国Brandenburg由土壤分离的解淀粉芽孢杆菌植物亚种或贝莱斯芽孢杆菌FZB24(也称为SB3615;DSM 96-2;J.Plant Dis.Prot.105,181-197,1998;例如来自Novozyme Biologicals,Inc.,USA的/>),在德国Brandenburg由土壤分离的解淀粉芽孢杆菌植物亚种或贝莱斯芽孢杆菌FZB42(DSM 23117;J.Plant Dis.Prot.105,181-197,1998;例如来自德国AbiTEP GmbH的Rhizo/>42),在Sutton Bonington,Nottinghamshire,U.K.至少在1988年以前由蚕豆分离的解淀粉芽孢杆菌植物亚种或贝莱斯芽孢杆菌MBI600(也称为1430;NRRL B-50595;US 2012/0149571 A1;例如来自BASFCorp.,USA的/>),在California,U.S.A.于1995年由桃园分离的解淀粉芽孢杆菌植物亚种或贝莱斯芽孢杆菌QST-713(NRRL B-21661;例如来自Bayer Crop Science LP,USA的/>MAX),在South Dakoda,U.S.A.于1992年分离的解淀粉芽孢杆菌植物亚种或贝莱斯芽孢杆菌TJ1000(也称为1BE;ATCC BAA-390;CA 2471555 A1;例如来自TJTechnologies,Watertown,SD,USA的QuickRootsTM);在以色列中部平原地区的土壤中分离的坚强芽孢杆菌CNCM I-1582,亲本菌株EIP-N1的变种(CNCM I-1556)(WO 2009/126473,US6,406,690;例如来自Bayer CropScience LP,USA的/>),在墨西哥由苹果树根围分离的短小芽孢杆菌GHA 25(IDAC 260707-01;例如来自Premier Horticulture,Quebec,加拿大的PRO-/>BX),至少在1993年以前由被嗜维管束欧文氏菌(Erwiniatracheiphila)侵染的黄瓜分离的也称为BU-F22和BU-F33的短小芽孢杆菌INR-7(NRRL B-50185,NRRL B-50153;US 8,445,255),至少在2008年以前在南非由禾草根围分离的短小芽孢杆菌KFP9F(NRRL B-50754;WO 2014/029697;例如来自南非BASF AgriculturalSpecialities(Pty)Ltd.的BAC-UP或FUSION-P),1998年由在Pohnpei,Federated Statesof Micronesia收集的土壤分离的短小芽孢杆菌QST 2808(NRRL B-30087;例如来自BayerCrop Science LP,USA的/>或/>Plus),简单芽孢杆菌ABU 288(NRRL B-50304;US 8,445,255),在北美由红甜菜头分离的也称为UD 1022或UD10-22的枯草芽孢杆菌FB17(ATCC PTN-11857;System.Appl.Microbiol.27,372-379,2004;US 2010/0260735;WO 2011/109395);在Ephraim,Wisconsin,U.S.A.于1987年由取自草坪的土壤分离的苏云金芽孢杆菌鲇泽亚种ABTS-1857(也称为ABG-6346;ATCC SD-1372;例如来自BioFa AG,Münsingen,德国的/>),在Brownsville,Texas,U.S.A.于1967年由病态棉红铃虫(Pink Bollworm)黑色幼虫分离的等同于HD-1的苏云金芽孢杆菌库斯塔克亚种ABTS-351(ATCC SD-1275;例如来自Valent BioSciences,IL,USA的/>DF),由E.saccharina幼虫尸体分离的苏云金芽孢杆菌库斯塔克亚种SB4(NRRL B-50753;例如来自南非BASFAgricultural Specialities(Pty)Ltd.的Beta/>),苏云金芽孢杆菌拟步行甲亚种NB-176-1,菌株NB-125的突变体,1982年由甲虫大黄粉虫(Tenebrio molitor)的死蛹分离的野生型菌株(DSM 5480;EP 585 215B1;例如来自瑞士Valent BioSciences的/>),球孢白僵菌GHA(ATCC 74250;例如来自Laverlam Int.Corp.,USA的/>22WGP),球孢白僵菌(B.bassiana)JW-1(ATCC 74040;例如来自意大利CBC(Europe)S.r.l.的/>),由龟甲虫Conchyloctenia punctata的幼虫分离的球孢白僵菌PPRI5339(NRRL 50757;例如来自南非BASF Agricultural Specialities(Pty)Ltd.的),在巴西里约热内卢分离的埃氏慢生根瘤菌(Bradyrhizobium elkanii)菌株SEMIA 5019(也称为29W)和在the State of Rio Grande do Sul于1967年由之前用北美分离物接种的区域分离并自从1968年用于商业接种体中的SEMIA 587(Appl.Environ.Microbiol.73(8),2635,2007;例如来自巴西BASF AgriculturalSpecialties Ltd.的GELFIX 5),在美国由Wisconsin大田分离的日本慢生根瘤菌532c(Nitragin61A152;Can.J.Plant.Sci.70,661-666,1990;例如来自加拿大BASFAgricultural Specialties Ltd.的/>Super),菌株USDA 138的日本慢生根瘤菌E-109变种(INTA E109,SEMIA 5085;Eur.J.Soil Biol.45,28-35,2009;Biol.Fertil.Soils 47,81-89,2011);由Appl.Environ.Microbiol.73(8),2635,2007已知的保藏于SEMIA的日本慢生根瘤菌菌株:自从1992年用于商业接种体中的由Embrapa-Cerrados从巴西Cerrados地区的土壤分离的SEMIA 5079(CPAC 15;例如来自巴西BASF Agricultural Specialties Ltd.的GELFIX 5或ADHERE 60),由巴西的Embrapa-Cerrados在实验室条件下得到并且自从1992年用于商业接种体中的日本慢生根瘤菌SEMIA5080,为最初在美国分离的SEMIA 586(CB259)的自然变体(CPAC 7;例如来自巴西BASFAgricultural Specialties Ltd.的GELFIX 5或ADHERE 60);在2008年由日本Nikko的土壤分离的伯克霍尔德氏菌A396(NRRL B-50319;WO2013/032693;Marrone Bio Innovations,Inc.,USA),由油菜分离的盾壳霉CON/M/91-08(WO 1996/021358;DSM 9660;例如来自德国Bayer CropScience AG的/>WG,/>WG),超敏(α-β)蛋白(Science257,85-88,1992;例如来自Plant Health Care plc,U.K.的MessengerTM或HARP-N-Tek),棉铃虫核型多角体病毒(HearNPV)(J.Invertebrate Pathol.107,112-126,2011;例如来自瑞士Adermatt Biocontrol的/>来自巴西Koppert的/>来自AgBiTechPty Ltd.,Queensland,澳大利亚的/>Max),棉铃虫单壳核型多角体病毒(HzSNPV)(例如来自Certis LLC,USA的/>),棉铃虫核型多角体病毒ABN-NPV-U(例如来自AgBiTech Pty Ltd.,Queensland,澳大利亚的/>),嗜菌异小杆线虫(例如来自BASFAgricultural Specialities Limited,UK的/>G),在Apopka,Florida,U.S.A.由紫贝天葵上的多毛绵蚧分离的玫烟色棒束Apopka-97(ATCC 20874;Biocontrol ScienceTechnol.22(7),747-761,2012;例如来自Certis LLC,USA的PFR-97TM或/>),在奥地利由苹果蠹蛾分离的也称为275或V275的金龟子绿僵菌变种F52(DSM 3884,ATCC90448;例如来自加拿大Novozymes Biologicals BioAg Group的/>),在以色列中部由葡萄分离的核果梅奇酵母277(US 6,994,849;NRRL Y-30752;例如来自以色列Agrogreen的原/>),在菲律宾由被感染的线虫卵分离的淡紫色拟青霉(Paecilomycesilacinus)251(AGAL 89/030550;WO1991/02051;Crop Protection 27,352-361,2008;例如来自德国Bayer CropScience AG的/>和来自Certis,USA的/>),至少在2008年以前在南非由禾草根围分离的蜂房芽孢杆菌NAS6G6(WO 2014/029697;NRRL B-50755;例如来自南非BASF Agricultural Specialities(Pty)Ltd.的BAC-UP),由来自包括德国在内的欧洲多地的土壤样品分离的类芽孢杆菌属(Paenibacillus)菌株:P.epiphyticus Lu17015(WO 2016/020371;DSM 26971),多粘类芽孢杆菌植物亚种(P.polymyxa ssp.plantarum)Lu16774(WO 2016/020371;DSM 26969),多粘类芽孢杆菌植物亚种(P.p.ssp.plantarum)菌株Lu17007(WO 2016/020371;DSM 26970);在Illinois,U.S.A.于2000中期由大豆田分离的拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)Pn1(ATCCSD-5833;Federal Register 76(22),5808,2011年2月2日;例如来自Syngenta CropProtection,LLC,USA的ClarivaTM PN),最初在加拿大Alberta由土壤分离的比莱青霉(也称为P.bilaii)菌株ATCC 18309(=ATCC 74319)、ATCC 20851和/或ATCC 22348(=ATCC74318)(Fertilizer Res.39,97-103,1994;Can.J.Plant Sci.78(1),91-102,1998;US 5,026,417,WO 1995/017806;例如来自加拿大Novozymes Biologicals BioAg Group的Jump),大虎杖提取物(EP 0307510 B1;例如来自MarroneBioInnovations,Davis,CA,USA的/>SC或来自德国BioFa AG的/>),斯氏小卷蛾线虫(例如来自BASF Agricultural Specialities Limited,UK的/>),斯氏夜蛾线虫(例如来自BioWorks,Inc.,USA的/>来自BASF AgriculturalSpecialities Limited,UK的/>),细黄链霉菌(Streptomyces microflavus)NRRL B-50550(WO 2014/124369;Bayer CropScience,德国),在南非分离的Trichodermaasperelloides JM41R(NRRL 50759;也称为顶孢木霉;例如来自南非BASF AgriculturalSpecialities(Pty)Ltd.的/>),也称为KRL-AG2的哈茨木霉T-22(ATCC 20847;BioControl 57,687-696,2012;例如来自BioWorks Inc.,USA的/>或来自Advanced Biological Marketing Inc.,Van Wert,OH,USA的SabrExTM)。
根据混合物的另一实施方案,该至少一种农药II选自L1)-L5)组:
L1)具有杀真菌、杀细菌、杀病毒和/或植物防御活化剂活性的微生物农药:出芽短梗霉DSM 14940和DSM 14941(L1.1),解淀粉芽孢杆菌AP-188(L.1.2),解淀粉芽孢杆菌植物亚种D747(L.1.3),解淀粉芽孢杆菌植物亚种FZB24(L.1.4),解淀粉芽孢杆菌植物亚种FZB42(L.1.5),解淀粉芽孢杆菌植物亚种MBI600(L.1.6),解淀粉芽孢杆菌植物亚种QST-713(L.1.7),解淀粉芽孢杆菌植物亚种TJ1000(L.1.8),短小芽孢杆菌GB34(L.1.9),短小芽孢杆菌GHA 25(L.1.10),短小芽孢杆菌INR-7(L.1.11),短小芽孢杆菌KFP9F(L.1.12),短小芽孢杆菌QST 2808(L.1.13),简单芽孢杆菌ABU 288(L.1.14),枯草芽孢杆菌FB17(L.1.15),盾壳霉CON/M/91-08(L.1.16),核果梅奇酵母NRRLY-30752(L.1.17),蜂房芽孢杆菌NAS6G6(L.1.18),P.epiphyticusLu17015(L.1.25),多粘类芽孢杆菌植物亚种Lu16774(L.1.26),多粘类芽孢杆菌植物亚种菌株Lu17007(L.1.27),比莱青霉ATCC 22348(L.1.19),比莱青霉ATCC 20851(L.1.20),比莱青霉ATCC 18309(L.1.21),细黄链霉菌NRRLB-50550(L.1.22),Trichodermaasperelloides JM41R(L.1.23),哈茨木霉T-22(L.1.24);
L2)具有杀真菌、杀细菌、杀病毒和/或植物防御活化剂活性的生物化学农药:超敏蛋白(L.2.1),大虎杖提取物(L.2.2);
L3)具有杀虫、杀螨、杀螺和/或杀线虫活性的微生物农药:坚强芽孢杆菌I-1582(L.3.1);苏云金芽孢杆菌鲇泽亚种ABTS-1857(L.3.2),苏云金芽孢杆菌库斯塔克亚种ABTS-351(L.3.3),苏云金芽孢杆菌库斯塔克亚种SB4(L.3.4),苏云金芽孢杆菌拟步行甲亚种NB-176-1(L.3.5),球孢白僵菌GHA(L.3.6),球孢白僵菌JW-1(L.3.7),球孢白僵菌PPRI5339(L.3.8),伯克霍尔德氏菌A396(L.3.9),棉铃虫核型多角体病毒(HearNPV)(L.3.10),棉铃虫核型多角体病毒(HzNPV)ABA-NPV-U(L.3.11),棉铃虫单壳核型多角体病毒(HzSNPV)(L.3.12),嗜菌异小杆线虫(L.3.13),玫烟色棒束孢Apopka-97(L.3.14),金龟子绿僵菌变种F52(L.3.15),淡紫色拟青霉(Paecilomyces lilacinus)251(L.3.16),拟斯扎瓦巴氏杆菌Pn1(L.3.17),斯氏小卷蛾线虫(L.3.18),斯氏夜蛾线虫(L.3.19);
L4)具有杀虫、杀螨、杀螺、信息素和/或杀线虫活性的生物化学农药:顺式-茉莉酮(L.4.1)、茉莉酮酸甲酯(L.4.2)、皂树提取物(L.4.3);
L5)具有植物逆境降低、植物生长调节剂、植物生长促进和/或产量提高活性的微生物农药:巴西固氮螺菌Ab-V5和Ab-V6(L.5.1),巴西固氮螺菌Sp245(L.5.2),埃氏慢生根瘤菌SEMIA 587(L.5.3),埃氏慢生根瘤菌SEMIA 5019(L.5.4),日本慢生根瘤菌532c(L.5.5),日本慢生根瘤菌E-109(L.5.6),日本慢生根瘤菌SEMIA 5079(L.5.7),日本慢生根瘤菌SEMIA 5080(L.5.8)。
此外,本发明涉及包含至少一种化合物I(组分1)和至少一种选自L)组的生物农药,尤其是至少一种选自如上所述的L1)和L2)组的生物农药(组分2)的混合物以及需要的话,至少一种合适助剂的农业化学组合物。
此外,本发明涉及包含至少另一种化合物I(组分1)和至少一种选自L)组的生物农药,尤其是至少一种选自如上所述的L3)和L4)组的生物农药(组分2)的混合物以及需要的话,至少一种合适助剂的农业化学组合物。
还优选包含选自L1)、L3)和L5)组,优选选自上面作为(L.1.2)、(L.1.3)、(L.1.4)、(L.1.5)、(L.1.6)、(L.1.7)、(L.1.8)、(L.1.10)、(L.1.11)、(L.1.12)、(L.1.13)、(L.1.14)、(L.1.15)、(L.1.17)、(L.1.18)、(L.1.19)、(L.1.20)、(L.1.21)、(L.1.25)、(L.1.26)、(L.1.27)、(L.3.1)、(L.3.9)、(L.3.16)、(L.3.17)、(L.5.1)、(L.5.2)、(L.5.3)、(L.5.4)、(L.5.5)、(L.5.6)、(L.5.7)、(L.5.8)、(L.4.2)和(L.4.1)表示的菌株,甚至更优选选自上面作为(L.1.2)、(L.1.6)、(L.1.7)、(L.1.8)、(L.1.11)、(L.1.12)、(L.1.13)、(L.1.14)、(L.1.15)、(L.1.18)、(L.1.19)、(L.1.20)、(L.1.21)、(L.3.1)、(L.3.9)、(L.3.16)、(L.3.17)、(L.5.1)、(L.5.2)、(L.5.5)、(L.5.6)、(L.4.2)和(L.4.1)表示的菌株的生物农药作为农药II(组分2)的混合物。这些混合物特别适合处理繁殖材料,即种子处理目的,并且同样特别适合土壤处理。这些种子处理混合物特别适合作物如禾谷类、玉米和豆科植物如大豆。
还优选包含选自L1)、L3)和L5)组,优选选自上面作为(L1.1)、(L.1.2)、(L.1.3)、(L.1.6)、(L.1.7)、(L.1.9)、(L.1.11)、(L.1.12)、(L.1.13)、(L.1.14)、(L.1.15)、(L.1.17)、(L.1.18)、(L.1.22)、(L.1.23)、(L.1.24)、(L.1.25)、(L.1.26)、(L.1.27)、(L.2.2)、(L.3.2)、(L.3.3)、(L.3.4)、(L.3.5)、(L.3.6)、(L.3.7)、(L.3.8)、(L.3.10)、(L.3.11)、(L.3.12)、(L.3.13)、(L.3.14)、(L.3.15)、(L.3.18)、(L.3.19)、(L.4.2)表示的菌株,甚至更优选选自上面作为(L.1.2)、(L.1.7)、(L.1.11)、(L.1.13)、(L.1.14)、(L.1.15)、(L.1.18)、(L.1.23)、(L.3.3)、(L.3.4)、(L.3.6)、(L.3.7)、(L.3.8)、(L.3.10)、(L.3.11)、(L.3.12)、(L.3.15)和(L.4.2)表示的菌株的生物农药作为农药II(组分2)的混合物。这些混合物特别适合叶面处理栽培植物,优选蔬菜、水果、葡萄藤、禾谷类、玉米、豆科植物如大豆。
包含活性成分的混合物的组合物可以通过常规方式,例如通过对化合物I的组合物所给方式制备。
当活的微生物,例如选自L1)、L3)和L5)组的农药II形成组合物的一部分时,该类组合物可以通过常规方式制备(例如H.D.Burges:Formulation of MicobialBiopesticides,Springer,1998;WO 2008/002371,US 6,955,912,US 5,422,107)。
I.合成实施例
步骤1—制备2,2,3-三甲基苯并二氢吡喃-4-酮肟
将盐酸羟胺(72.87g,3eq)加入2,2,3-三甲基苯并二氢吡喃-4-酮(1eq,66.5g)在吡啶(423ml,15eq)中的溶液中并将反应混合物在85℃下搅拌18小时。将反应溶液倾入水(1000ml)中并将该溶液用庚烷萃取,依次用水和盐水洗涤并在无水硫酸镁上干燥。真空除去溶剂而以褐色粉末得到标题化合物(66.6)。在没有进一步提纯下直接使用该标题化合物。
1H NMR(400MHz,CDCl3):μ[ppm]:9.15(s,1H),7.75(dd,J=7.9,1.7Hz,1H),7.26(dd,J=7.1,1.5Hz,1H),6.91(ddd,J=8.2,7.2,1.2Hz,1H),6.86(dd,J=8.3,1.2Hz,1H),3.39(q,J=7.0Hz,1H),1.45(s,3H),1.27(s,3H),1.13(d,J=7.0Hz,3H)。
步骤2—制备2,2,3-三甲基-3,4-二氢-1,4-苯并氧氮杂-5-酮
在低于30℃的温度下将2,2,3-三甲基苯并二氢吡喃-4-酮肟(66g,1eq)加入亚硫酰氯(80,3.5eq)中并将反应混合物在50℃下搅拌17小时。在真空除去亚硫酰氯之后将残余物倾入1,4-二烷(500ml)和水(200ml)中并在80℃下搅拌1小时。在真空除去1,4-二/>烷之后将所得残余物用乙酸乙酯萃取,依次用水和盐水洗涤并在无水硫酸镁上干燥。真空除去溶剂,粗产物通过在硅胶上使用庚烷/MTBE作为洗脱剂的快速层析提纯而以白色粉末得到标题化合物(25.4g)。
1H NMR(400MHz,CDCl3):μ[ppm]:7.74(dd,J=7.7,1.8Hz,1H),7.44(td,J=7.7,1.8Hz,1H),7.20(td,J=7.5,1.1Hz,1H),6.98(dd,J=8.1,1.1Hz,1H),6.44(s,1H),3.37(qd,J=6.9,5.2Hz,1H),1.39(s,3H),1.29(s,3H),1.20(d,J=6.9Hz,3H)。
步骤3—制备5-氯-2,2,3-三甲基-3H-1,4-苯并氧氮杂
将2,2,3-三甲基-3,4-二氢-1,4-苯并氧氮杂-5-酮(10g,1eq)与磷酰氯(100ml)和11.67g五氯化磷(V)(1.15eq)的混合物在110℃下热搅拌2小时。在冷却之后将反应溶液真空浓缩,用二氯甲烷稀释,用饱和碳酸钠溶液洗涤两次并在无水硫酸镁上干燥。真空除去溶剂得到粗产物(10.8g)。在没有进一步提纯下直接使用该标题化合物。/>
步骤4—制备5-[6-二氟甲氧基-5-甲基-3-吡啶基]-2,2,3-三甲基-3H-1,4-苯并氧氮杂
将[6-二氟甲基-5-甲基-3-吡啶基]硼酸(3.11g,1.2eq)、碳酸钾(3.83g,2eq)、氧化银(1.61,0.5eq)和二氯二(三苯基膦)钯(II)(490mg,0.05eq)加入5-氯-2,2,3-三甲基-3H-1,4-苯并氧氮杂(3.1g,1eq)在无水四氢呋喃(57mL)中的溶液中,并将该混合物在氩气气氛下于80℃搅拌18小时。在冷却之后将反应溶液用乙酸乙酯稀释,将该溶液依次用水和盐水洗涤,在无水硫酸镁上干燥并真空浓缩。粗产物通过在二氧化硅RP-18上使用乙腈/水作为洗脱剂的高效液相色谱法提纯而以白色粉末得到标题化合物(1.5g)。
1H NMR(400MHz,CDCl3):μ[ppm]:8.58(d,J=1.9Hz,1H),7.92(s,1H),7.46(t,J=7.7Hz,1H),7.18(td,J=7.5,1.2Hz,1H),7.09(td,J=7.7,1.4Hz,2H),6.73(t,J=54.5Hz,1H),3.28(d,J=6.8Hz,1H),2.54(d,J=2.2Hz,3H),1.59(s,3H),1.45(s,3H),1.39(s,3H)。
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微试验
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。
实施例1—在微滴定板试验中对灰霉病灰葡萄孢的活性
将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入灰葡萄孢在生物麦芽或酵母-细菌蛋白胨-乙酸钠水溶液中的孢子悬浮液。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。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-8、Ex-9、Ex-10和Ex-11的活性物质处理的样品显示出0%病原体生长。
实施例2—在微滴定板试验中对大刀镰孢的活性
将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入大刀镰孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。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。
在该试验中,分别用31ppm实施例Ex-2和Ex-3的活性物质处理的样品显示出1%病原体生长。
实施例3—在微滴定板试验中对苹果黑星病(Venturia inaequalis)的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入灰葡萄孢(Botrci cinerea)在生物麦芽或酵母-细菌蛋白胨-乙酸钠水溶液中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-4、Ex-12(在50ppm下)、Ex-18、Ex-21、Ex-22、Ex-24、Ex-28、Ex-29、Ex-31、Ex-36、Ex-44、Ex-45、Ex-47的活性物质处理的样品显示出至多20%病原体生长。
实施例4—在微滴定板试验中对灰霉病灰葡萄孢的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入灰葡萄孢在生物麦芽或酵母-细菌蛋白胨-乙酸钠水溶液中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-3、Ex-4、Ex-6、Ex-7、Ex-8、Ex-9、Ex-11、Ex-12、Ex-13、Ex-15、Ex-16、Ex-17、Ex-19、Ex-20、Ex-21、Ex-22、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-38、Ex-39、Ex-43、Ex-45、Ex-46、Ex-47、Ex-48、Ex-49、Ex-50、Ex-51、Ex-52+Ex-52作为外消旋体、Ex-68、Ex-69的活性物质处理的样品显示出至多1%病原体生长。
实施例5—在微滴定板试验中对大刀镰孢的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入大刀镰孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-3、Ex-11、Ex-26、Ex-27、Ex-30、Ex-34、Ex-46、Ex-48、Ex-49、Ex-52和Ex-53作为外消旋体的活性物质处理的样品显示出至多9%病原体生长。
实施例6—在微滴定板试验中对小麦上由小麦壳针孢引起的斑枯病的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入小麦壳针孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-21、Ex-28、Ex-33、Ex-47、Ex-48的活性物质处理的样品显示出至多18%病原体生长。
实施例7—在微滴定板试验中对雪霉叶枯菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入雪霉叶枯菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-7、Ex-9、Ex-11、Ex-12、Ex-13、Ex-15、Ex-16、Ex-19、Ex-20、Ex-21、Ex-22、Ex-23、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-37、Ex-38、Ex-39、Ex-41、Ex-44、Ex-45、Ex-46、Ex-47、Ex-52和Ex-53作为外消旋体、Ex-68、Ex-69的活性物质处理的样品显示出至多19%病原体生长。
实施例8—在微滴定板试验中对瓜类炭疽菌(Colletotrichum orbiculare)的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入瓜类炭疽菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-7、Ex-9、Ex-11、Ex-12、Ex-13、Ex-16、Ex-19、Ex-22、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-32、Ex-33、Ex-34、Ex-36、Ex-41、Ex-45、Ex-52和Ex-53作为外消旋体、Ex-69的活性物质处理的样品显示出至多15%病原体生长。
实施例9—在微滴定板试验中对颖枯球腔菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入颖枯球腔菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-7、Ex-9、Ex-11、Ex-12、Ex-13、Ex-15、Ex-16、Ex-17、Ex-18、Ex-19、Ex-20、Ex-21、Ex-22、Ex-23、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-37、Ex-38、Ex-39、Ex-40、Ex-42、Ex-43、Ex-44、Ex-45、Ex-46、Ex-47、Ex-52和Ex-53作为外消旋体、Ex-68、Ex-69的活性物质处理的样品显示出至多12%病原体生长。
实施例10—在微滴定板试验中对禾本科镰孢(Fusarium gramminearis)的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入禾本科镰孢分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-2、Ex-27、Ex-30、Ex-34的活性物质处理的样品显示出至多16%病原体生长。
实施例11—在微滴定板试验中对核果链核盘菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入核果链核盘菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-7、Ex-9、Ex-10、Ex-11、Ex-12、Ex-13、Ex-15、Ex-16、Ex-17、Ex-18、Ex-20、Ex-21、Ex-22、Ex-23、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-40、Ex-44、Ex-45、Ex-47、Ex-52和Ex-53作为外消旋体、Ex-68、Ex-69的活性物质处理的样品显示出至多20%病原体生长。
实施例12—在微滴定板试验中对玉蜀黍黑粉菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入玉蜀黍黑粉菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-24、Ex-41的活性物质处理的样品显示出0%病原体生长。
实施例13—在微滴定板试验中对圆核腔菌Qoi(FL129)抗性分离物的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入圆核腔菌Qoi(FL129)抗性分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-7、Ex-9、Ex-10、Ex-11、Ex-12、Ex-13、Ex-15、Ex-16、Ex-19、Ex-20、Ex-21、Ex-22、Ex-23、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-32、Ex-33、Ex-34、Ex-36、Ex-37、Ex-38、Ex-39、Ex-41、Ex-42、Ex-43、Ex-44、Ex-45、Ex-47、Ex-52和Ex-53作为外消旋体、Ex-68、Ex-69的活性物质处理的样品显示出至多19%病原体生长。
实施例14—在微滴定板试验中对斑点小球腔菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入斑点小球腔菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-11、Ex-12、Ex-15、Ex-16、Ex-17、Ex-18、Ex-19、Ex-20、Ex-21、Ex-22、Ex-23、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-37、Ex-38、Ex-39、Ex-41、Ex-42、Ex-43、Ex-44、Ex-45、Ex-46、Ex-68、Ex-69的活性物质处理的样品显示出至多19%病原体生长。
实施例15—在微滴定板试验中对致病疫霉的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入致病疫霉在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-8、Ex-9、Ex-10、Ex-11、Ex-12、Ex-13、Ex-15、Ex-20、Ex-23、Ex-24、Ex-31的活性物质处理的样品显示出至多19%病原体生长。
实施例16—在微滴定板试验中对斐济球腔菌(Mycosphorella fijiensi)的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入斐济球腔菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-6、Ex-15、Ex-20、Ex-21、Ex-22、Ex-23、Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-37、Ex-38、Ex-39、Ex-44、Ex-45的活性物质处理的样品显示出至多20%病原体生长。
实施例17—在微滴定板试验中对黄瓜褐斑病菌的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入黄瓜褐斑病菌分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-44、Ex-45、Ex-47、Ex-69的活性物质处理的样品显示出至多16%病原体生长。
实施例18—在微滴定板试验中对黄瓜褐斑病菌(CORYCA-G)G413A突变体的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入黄瓜褐斑病菌(CORYCA-G)G413A突变体分离物在DOB培养基(pH 7)中的孢子悬浮液。
在该试验中,分别用31ppm实施例Ex-24、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-36、Ex-38、Ex-44、Ex-45、Ex-47、Ex-69的活性物质处理的样品显示出至多18%病原体生长。
将测量的参数与不含活性化合物的对照方案的生长(100%)以及不含真菌的空白值相比较,以确定病原体在相应活性化合物中的相对生长百分数。
温室
将该化合物溶于溶剂/乳化剂比率(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。
实施例19—在青椒叶子上对灰葡萄孢的预防性杀真菌防治
使青椒幼苗在盆中生长至4-5叶阶段。将这些植株用含有下表所述浓度的活性成分或混合物的前述喷雾液喷雾至滴流。第二天将植株用含有灰葡萄孢的孢子悬浮液的生物麦芽或DOB水溶液接种。然后将植株立即转移至潮湿室中。在22-24℃和饱和相对湿度下5天之后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。
在该试验中,分别用250ppm实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-8、Ex-9、Ex-12、Ex-13、Ex-16和Ex-18的活性物质处理的样品显示出至多15%的病原体生长,而未被处理植株90%感染。
实施例20—在油菜上对由核盘菌引起的白绢病的预防性杀真菌防治
使油菜在盆中生长至13-14叶阶段。将这些植株用含有下表所述浓度的活性成分或其混合物的前述喷雾液喷雾至滴流。风干植株。第二天将施药油菜花瓣用25μl 2.5%甲基纤维素固定于第1和2片叶上。将25μl核盘菌孢子悬浮液用移液管移到各固定的油菜花瓣上。在20℃和60%相对湿度下14天之后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。
在该试验中,分别用100g/ha实施例Ex-1、Ex-2、Ex-3、Ex-4、Ex-7、Ex-8、Ex-11、Ex-12、Ex-15、Ex-17、Ex-20、Ex-21、Ex-22、Ex-25、Ex-26、Ex-27、Ex-28、Ex-30、Ex-31、Ex-32、Ex-33、Ex-34、Ex-40、Ex-45、Ex-47的活性物质处理的样品显示出至多15%的病原体生长,而未被处理植株100%感染。
实施例21—在青椒叶子上对灰葡萄孢的预防性杀真菌防治
使青椒幼苗在盆中生长至4-5叶阶段。将这些植株用含有下表所述浓度的活性成分或混合物的前述喷雾液喷雾至滴流。第二天将植株用含有灰葡萄孢的孢子悬浮液的生物麦芽或DOB水溶液接种。然后将植株立即转移至潮湿室中。在22-24℃和饱和相对湿度下5天之后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。
在该试验中,分别用100g/ha实施例Ex-8、Ex-12、Ex-25、Ex-26、Ex-27的活性物质处理的样品显示出至多18%的病原体生长,而未被处理植株100%感染。
实施例22—在青椒叶子上对灰葡萄孢的长效防治
使青椒幼苗在盆中生长至4-5叶阶段。将这些植株用含有下表所述浓度的活性成分或混合物的前述喷雾液喷雾至滴流。然后将植株在温室中栽培7天,随后用含有灰葡萄孢的孢子悬浮液的生物麦芽或DOB水溶液接种。然后将植株立即转移至潮湿室中。在22-24℃和饱和相对湿度下5天之后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。
在该试验中,分别用100g/ha实施例Ex-21、Ex-25、Ex-26、Ex-27、Ex-28、Ex-29、Ex-45、Ex-47、Ex-69的活性物质处理的样品显示出至多14%的病原体生长,而未被处理植株90%感染。
对比例
实施例1—在小麦上对由小麦壳针孢引起的斑枯病的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入小麦壳针孢在生物麦芽或酵母-细菌蛋白胨-甘油或DOB水溶液中的孢子悬浮液。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。
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实施例2—对由颖枯球腔菌引起的小麦叶斑病的活性
将活性化合物分开在二甲亚砜中配制成浓度为10000ppm的储备溶液。将储备溶液根据比率混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入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。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。
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Claims (15)
1.作为杀真菌剂的式I化合物及其N-氧化物和可农用盐:
其中
R1为H;
R2在每种情况下独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、O-C1-C6烷基、C3-C6环烷基;R3在每种情况下独立地选自C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、C2-C6卤代链烯基、C2-C6炔基、O-C1-C6烷基、C3-C6环烷基;
R4为H;
R5在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中所述结构部分未被取代或者被1-3个相互独立地选自如下的基团R5a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;
R6在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中R6的所述结构部分未被取代或者被1-3个相互独立地选自如下的基团R6a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;或者R5和R6与它们所键合的C原子一起形成=O;或者
R5和R6与它们所键合的C原子一起形成C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环,其中所述环烷基或杂环可以未被取代或者被卤素、C1-C6烷基、C1-C6卤代烷基取代;
R7在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基、苯基、苄基,其中所述结构部分未被取代或者被1-3个相互独立地选自如下的基团R7a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;
R8在每种情况下独立地选自H、F、CN、C1-C6烷基、C1-C6卤代烷基、
C2-C6链烯基、苯基、苄基,其中所述结构部分未被取代或者被1-3个相互独立地选自如下的基团R8a取代:
卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基;或者R7和R8与它们所键合的C原子一起形成C3-C6环烷基或含有1、2或3个选自O和S的杂原子的3-6员饱和杂环;
X在每种情况下独立地选自卤素、CN、C1-C6烷基、C1-C6卤代烷基、O-C1-C6烷基、O-C1-C6卤代烷基、C3-C6环烷基、C2-C6链烯基、C2-C6炔基;
n为0、1、2或3,
条件是R5、R6、R7、R8不能全部为H。
2.权利要求1的化合物,其中R2为C1-C6烷基或O-C1-C6烷基。
3.权利要求1或2的化合物,其中R2为CH3。
4.权利要求1-3中任一项的化合物,其中R3选自C1-C6烷基或C1-C6卤代烷基。
5.权利要求1-4中任一项的化合物,其中R3为CH3或CHF2。
6.权利要求1-5中任一项的化合物,其中R5为H或C1-C6烷基。
7.权利要求1-6中任一项的化合物,其中R6选自H或C1-C6烷基。
8.权利要求1-7中任一项的化合物,其中R5和R6与它们所键合的C原子一起形成=O或C3-C6环烷基。
9.权利要求1-8中任一项的化合物,其中R7为H或C1-C6烷基。
10.权利要求1-9中任一项的化合物,其中R8选自C1-C6烷基、苯基、苄基,其中所述结构部分未被取代或者被1-3个相互独立地选自O-C1-C6烷基的基团R5a取代。
11.权利要求1-10中任一项的化合物,其中X选自卤素、C1-C6烷基、O-C1-C6烷基、O-C1-C6卤代烷基。
12.权利要求1-11中任一项的化合物,其中X选自F、CH3、C2H5、OCH3、OCHF2、OCF3。
13.一种包含一种如权利要求1-12中任一项所定义的式I化合物、其N-氧化物或可农用盐的组合物。
14.一种制备式I化合物的方法,包括使式Y化合物反应:
其中R5、R6、R7、R8和Xn如权利要求1-12中任一项所定义且Hal为卤素。
15.式Y化合物:
其中
R5选自H、C1-C6烷基,
R6选自H、C1-C6烷基,或者
R5和R6与它们所键合的C原子一起形成C3-C6环烷基;
R7选自H、C1-C6烷基,
R8选自H、C1-C6烷基,或者
R7和R8与它们所键合的C原子一起形成C3-C6环烷基;
X为卤素、C1-C6烷基,
n为0、1或2。
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WO2022243111A1 (en) | 2022-11-24 |
KR20240008856A (ko) | 2024-01-19 |
AU2022279357A1 (en) | 2023-11-30 |
BR112023024005A2 (pt) | 2024-01-30 |
CL2023003418A1 (es) | 2024-04-26 |
CA3218900A1 (en) | 2022-11-24 |
AR125907A1 (es) | 2023-08-23 |
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