CN103717579B - 杀真菌的取代的1-{2-[2-卤代-4-(4-卤代苯氧基)苯基]-2-烷氧基-2-环基乙基}-1h-[1,2,4]三唑化合物 - Google Patents
杀真菌的取代的1-{2-[2-卤代-4-(4-卤代苯氧基)苯基]-2-烷氧基-2-环基乙基}-1h-[1,2,4]三唑化合物 Download PDFInfo
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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Abstract
本发明涉及如说明书所定义的式I的取代的1‑{2‑[2‑卤代‑4‑(4‑卤代苯氧基)苯基]‑2‑烷氧基‑2‑环基乙基}‑1H‑[1,2,4]三唑化合物及其N‑氧化物和盐,制备这些化合物的方法和中间体以及包含至少一种该类化合物的组合物。本发明还涉及该类化合物和组合物在防治有害真菌中的用途以及涂有至少一种该类化合物的种子。
Description
本发明涉及用于防治植物病原性真菌的杀真菌的1-{2-[2-卤代-4-(4-卤代苯氧基)苯基]-2-烷氧基-2-环基(cyclyl)乙基}-1H-[1,2,4]三唑化合物及其N-氧化物和盐,防治植物病原性真菌的用途和方法以及涂有至少一种该化合物的种子。本发明还是涉及制备这些化合物的方法、中间体和包含至少一种该化合物的组合物。
EP0126430A2涉及抗真菌的下式的取代的1H-[1,2,4]三唑化合物:
其中R3尤其可以为任选被1-3个卤素、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基、C1-C6烷基、苯氧基、卤代苯氧基、苯基、苄基、卤代苄基、硝基和/或氰基取代的苯基,并且其中R1可以为任选取代的C1-C12烷基,C3-C8环烷基,任选被1-3个卤素、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6烷氧基、C1-C6烷基、苯氧基、卤代苯氧基、苯基、苄基、卤代苄基、硝基和/或氰基取代的苯基,或任选被1-3个卤素、C1-C6卤代烷基、C1-C6烷氧基、C1-C6烷基、硝基和/或氰基取代的苄基。
本发明化合物与上述出版物中所述那些的不同在于特定的2-[2-卤代-4-(4-卤代苯氧基)苯基]和本文所定义的特定环状R1基团的组合。DE3801233A1涉及式I的杀微生物剂:
其中R1为卤素且R2为卤素或甲基,R3为烷基、卤代烷基、烷氧基烷基、链烯基、炔基或环丙基。J.Agric.Fod Chem.2009,57,4854-4860涉及某些2-芳基苯基醚-3-(1H-1,2,4-三唑-1-基)丙-2-醇衍生物的合成和杀真菌评价。
在许多情况下,尤其是在低施用率下,已知杀真菌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有害真菌具有改进活性和/或更宽活性谱的化合物。
该目的通过对植物病原性有害真菌具有良好杀真菌活性的取代的1-{2-[2-卤代-4-(4-卤代苯氧基)苯基]-2-烷氧基-2-环基乙基}-1H-[1,2,4]三唑化合物实现。
因此,本发明涉及式I化合物及其N-氧化物和可农用盐:
其中
X1、X2相互独立地选自卤素;
R1为C3-C8环烷基、C3-C8环烷基-C1-C4烷基、苯基、苯基-C1-C4烷基、苯基-C2-C4链烯基或苯基-C2-C4炔基;
R2为C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、苯基、苯基-C1-C4烷基、苯基-C2-C4链烯基或苯基-C2-C4炔基;
其中R1和/或R2的脂族结构部分可以带有1、2、3或至多最大可能数的相同或不同基团Ra,后者相互独立地选自:
Ra:卤素、CN、硝基、C1-C4烷氧基和C1-C4卤代烷氧基;
其中R2的环烷基和/或苯基结构部分可以带有1、2、3、4、5或至多最大数目的相同或不同基团Rb,后者相互独立地选自:
Rb:卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。
此外,本发明涉及这些化合物在防治有害真菌中的用途和涂有至少一种该类化合物的种子以及包含至少一种该类式I化合物的组合物。
此外,本发明涉及制备式I化合物的方法以及中间体如式Va、VI、VII、VIII、XI、XII和XIII化合物。
术语“化合物I”涉及式I化合物。同样,该术语适用于所有子式,例如“化合物I.A”涉及式I.A化合物或“化合物XII”涉及式XII化合物,等等。
化合物I可以类似于已知的现有技术方法(参见J.Agric.Food Chem.(2009)57,4854-4860;EP0275955A1;DE4003180A1;EP0113640A2;EP0126430A2)通过各种途径以及通过下列方案和本申请试验部分中的合成途径得到。
在第一种方法中,例如在第一步中使其中X1和X2如本文所定义的卤代苯酚II与其中X3表示I或Br的衍生物IIIa尤其是其中Y为F或Cl的溴代衍生物III反应,优选在碱存在下反应。然后通过与金属转移试剂如异丙基卤化镁反应而将所得化合物IVa,尤其是IV(其中X3为Br)转化成格利雅试剂并随后与乙酰氯优选在无水条件下且任选在催化剂如CuCl、AlCl3、LiCl及其混合物存在下反应,得到苯乙酮类V。这些化合物V例如可以优选在有机溶剂如乙醚、甲基叔丁基醚(MTBE)、甲醇或乙酸中用溴或氯气卤代。然后可以使其中“Hal”表示“卤素”如Br或Cl的所得化合物VI与1H-1,2,4-三唑优选在溶剂如四氢呋喃(THF)、二甲基甲酰胺(DMF)、甲苯存在下且在碱如碳酸钾、氢氧化钠或氢化钠存在下反应而得到化合物VII。使这些三唑化合物VII与其中R1如本文所定义且M为MgBr、MgCl、Li或Na的格利雅试剂R1-M(例如苯基烷基-MgBr或有机锂试剂苯基烷基-Li)反应,优选在无水条件下反应,得到化合物VIII。任选可以使用路易斯酸如LaCl3×2LiCl或MgBr2×OEt2。使这些化合物VIII与R2-LG反应,其中R1如上所定义且LG表示可亲核置换的离去基团如卤素、烷基磺酰基、烷基磺酰氧基和芳基磺酰氧基,优选氯、溴或碘,特别优选溴,优选在碱如NaH存在下在合适的溶剂如THF中反应,形成化合物I。化合物I的制备可以由下列方案说明:
在得到化合物I的第二种方法中,在第一步中使衍生物IIIa,尤其是溴代衍生物III例如与异丙基溴化镁反应,然后与其中R1如本文所定义的酰氯试剂IX(例如乙酰氯)优选在无水条件下且任选在催化剂如CuCl、AlCl3、LiCl及其混合物存在下反应,得到化合物X。或者,可以使化合物IIIc例如式IIIb的1,3-二氯苯与其中R1如上所定义的酰氯试剂IX(例如乙酰氯)优选在催化剂如AlCl3存在下反应。然后使酮X与酚类II优选在碱存在下反应而得到化合物Va。化合物Va还可以类似于对化合物V所述的第一种方法得到。
然后使中间体Va与三甲基(氧化)锍卤化物,优选碘化物,优选在碱如氢氧化钠存在下反应。然后使环氧化物XI与1H-1,2,4-三唑优选在碱如碳酸钾存在下且优选在有机溶剂如DMF存在下反应而得到化合物VIII。使这些化合物VIII与R2-LG反应,其中R2如上所定义且LG表示可亲核置换的离去基团如卤素、烷基磺酰基、烷基磺酰氧基和芳基磺酰氧基,优选氯、溴或碘,特别优选溴,优选在碱存在下反应而形成化合物I,后者随后可以如上所述烷基化。化合物I的制备可以由下列方案说明:
在第三种方法中,通过与醇R2OH优选在酸性条件下反应而使可以根据本文所述第二种方法得到的中间体XI的环氧化物环裂解。然后使所得化合物XII与卤化试剂或磺化试剂如PBr3、PCl3、甲磺酰氯、甲苯磺酰氯或亚硫酰氯反应而得到其中LG为可亲核置换的离去基团如卤素、烷基磺酰基、烷基磺酰氧基和芳基磺酰氧基,优选氯、溴或碘,特别优选溴或烷基磺酰基的化合物XIII。然后使化合物XIII与1H-1,2,4-三唑反应而得到化合物I。化合物I的制备可以由下列方案说明:
若各化合物I不能通过上述途径得到,则可以通过衍生其他化合物I制备它们。
N-氧化物可以根据常规氧化方法由化合物I制备,例如通过用有机过酸如间氯过苯甲酸(参见WO03/64572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。
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具有本文所定义的含义。
本发明还涉及新的式Va化合物:
其中变量R1、X1、X2如本文所定义,优选如对式I所定义。在本发明化合物Va的具体实施方案中,取代基R1、X1、X2如表1-84、表84a-84w、表85-168和表168a-168w中对化合物I所定义,其中各取代基相互独立地或以任何组合为具体实施方案。
本发明的另一实施方案是新的式VI化合物:
其中变量X1、X2如本文所定义,优选如对式I所定义,并且其中Hal表示卤素,尤其是Cl或Br。根据一个优选实施方案,在化合物VI中的Hal表示Br。
本发明的另一实施方案是新的式VII化合物:
其中变量X1、X2如本文所定义,优选如对式I所定义。在本发明化合物VII的具体实施方案中,取代基X1、X2如表1-84、表84a-84w、表85-168和表168a-168w所定义,其中各取代基相互独立地或以任何组合为具体实施方案。
本发明的另一实施方案是新的式VIII化合物:
其中变量X1、X2和R1如本文所定义,优选如对式I所定义,如下化合物除外:
1)其中X1和X2为Cl且R1为C3H5(环丙基)、1-Cl-环丙基、1-F-环丙基、C4H7、C6H11(环己基)、CH2-C3H5、C5H9(环戊基)、CH(CH3)C3H5、1-甲基环丙基或1-CN-环丙基的化合物;以及
2)其中X1和X2为Cl且R1为如下结构部分AR1的化合物:
其中
#表示与式VIII的连接点,
X为C1-C4链烷二基、C2-C4炔二基或键;
R为卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基;
n为整数且为0、1、2、3、4或5;以及
3)其中X1和X2为Cl且R1为CH=CHC6H5、CH=CH(4-Cl-C6H4)、CH=CH(2,4-Cl2-C6H3)、CH=CH(2,6-Cl2-C6H3)、CH=CH(4-CH3-C6H4)、CH=CH(4-OCH3-C6H4)、CH=CH(3,4-Cl2-C6H3)、CH=CH(2-F-C6H4)、CH=CH(4-NO2-C6H4)、CH=CH(2-NO2-C6H4)、CH=CH(2-Cl-C6H4)、CH=CH(4-F-C6H4)或CH=CH(4-C2H5-C6H4)的化合物。
根据一个实施方案,X1、X2和R1如本文所定义,优选如对式I所定义,如下化合物除外:
1)其中X1和X2为Cl且R1为C3-C8环烷基或C3-C8环烷基-C1-C4烷基的化合物,其中R1的脂族基团未被取代或者带有1、2、3或4个CN取代基;以及其中R1的环烷基结构部分未被取代或者带有1、2、3或至多最大数目的相同或不同基团Rb,后者相互独立地选自卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基;以及2)其中X1和X2为Cl且R1为如下结构部分AR1的化合物:
其中
#表示与式VIII的连接点,
X为C1-C4链烷二基、C2-C4炔二基或键;
R为卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基;
n为整数且为0、1、2、3、4或5;以及
3)其中X1和X2为Cl且R1为CH=CHC6H5、CH=CH(4-Cl-C6H4)、CH=CH(2,4-Cl2-C6H3)、CH=CH(2,6-Cl2-C6H3)、CH=CH(4-CH3-C6H4)、CH=CH(4-OCH3-C6H4)、CH=CH(3,4-Cl2-C6H3)、CH=CH(2-F-C6H4)、CH=CH(4-NO2-C6H4)、CH=CH(2-NO2-C6H4)、CH=CH(2-Cl-C6H4)、CH=CH(4-F-C6H4)或CH=CH(4-C2H5-C6H4)的化合物。
根据VIII的一个具体实施方案,X1和X2不同时为Cl。
化合物VIII也如本文对式I化合物所述适合作为杀真菌剂。具体优选的化合物VIII是下列C-1至C-86,其中各化合物对应于表C的一行:
表C:式VIII化合物C-1至C-86:
本发明的另一实施方案是新的式XI化合物:
其中变量X1、X2和R1如本文所定义,优选如对式I所定义,如下化合物除外:
1)其中X1和X2为Cl且R1为C3H5(环丙基)、1-Cl-环丙基、1-F-环丙基、C4H7、C6H11(环己基)、CH2-C3H5、C5H9(环戊基)、CH(CH3)C3H5、1-甲基环丙基或1-CN-环丙基的化合物;以及
2)其中X1和X2为Cl且R1为如下结构部分AR1的化合物:
其中
#表示与式VIII的连接点,
X为C1-C4链烷二基、C2-C4炔二基或键;
R为卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基;
n为整数且为0、1、2、3、4或5;以及
3)其中X1和X2为Cl且R1为CH=CHC6H5、CH=CH(4-Cl-C6H4)、CH=CH(2,4-Cl2-C6H3)、CH=CH(2,6-Cl2-C6H3)、CH=CH(4-CH3-C6H4)、CH=CH(4-OCH3-C6H4)、CH=CH(3,4-Cl2-C6H3)、CH=CH(2-F-C6H4)、CH=CH(4-NO2-C6H4)、CH=CH(2-NO2-C6H4)、CH=CH(2-Cl-C6H4)、CH=CH(4-F-C6H4)或CH=CH(4-C2H5-C6H4)的化合物。
根据一个实施方案,X1、X2和R1如本文所定义,优选如对式I所定义,如下化合物除外:
1)其中X1和X2为Cl且R1为C3-C8环烷基或C3-C8环烷基-C1-C4烷基的化合物,其中R1的脂族基团未被取代或者带有1、2、3或4个CN取代基;以及其中R1的环烷基结构部分未被取代或者带有1、2、3或至多最大数目的相同或不同基团Rb,后者相互独立地选自卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基;以及2)其中X1和X2为Cl且R1为如下结构部分AR1的化合物:
其中
#表示与式VIII的连接点,
X为C1-C4链烷二基、C2-C4炔二基或键;
R为卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或
C1-C4卤代烷氧基;
n为整数且为0、1、2、3、4或5;以及
3)其中X1和X2为Cl且R1为CH=CHC6H5、CH=CH(4-Cl-C6H4)、CH=CH(2,4-Cl2-C6H3)、CH=CH(2,6-Cl2-C6H3)、CH=CH(4-CH3-C6H4)、CH=CH(4-OCH3-C6H4)、CH=CH(3,4-Cl2-C6H3)或CH=CH(2-F-C6H4)的化合物。
根据XI的一个具体实施方案,X1和X2不同时为Cl。
具体的优选化合物XI为下列D-1至D-86,其中各化合物对应于表D的一行:
表D:式XI化合物D-1至D-86:
本发明的另一实施方案是新的式XII化合物:
其中变量X1、X2、R1和R2如本文所定义,优选如对式I所定义。在本发明化合物XII的具体实施方案中,取代基X1、X2、R1和R2如表1-84、表84a-84w、表85-168和表168a-168w中所定义,其中各取代基相互独立地或以任何组合为具体实施方案。
本发明的另一实施方案是新的式XIII化合物:
其中变量X1、X2、R1和R2如本文所定义,优选如对式I所定义,其中LG表示如上所定义的离去基团。在本发明化合物XIII的具体实施方案中,取代基X1、X2、R1和R2如表1-84、表84a-84w、表85-168和表168a-168w中所定义,其中各取代基相互独立地或以任何组合为具体实施方案。
在本文所给变量的定义中,使用通常为所述取代基的代表的集合性术语。术语“Cn-Cm”显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”是指氟、氯、溴和碘。
术语“C1-C6烷基”是指具有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”是指具有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“C2-C4链烯基”是指具有2-4个碳原子和在任意位置的双键的直链或支化不饱和烃基,如乙烯基、1-丙烯基、2-丙烯基(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。同样,术语“C2-C6链烯基”是指具有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。
术语“C2-C4炔基”是指具有2-4个碳原子且含有至少一个叁键的直链或支化不饱和烃基,如乙炔基、丙-1-炔基、丙-2-炔基(炔丙基)、丁-1-炔基、丁-2-炔基、丁-3-炔基、1-甲基丙-2-炔基。同样,术语“C2-C6炔基”是指具有2-6个碳原子和至少一个叁键的直链或支化不饱和烃基。
术语“C1-C4卤代烷基”是指具有1-4个碳原子的直链或支化烷基,其中这些基团中的部分或所有氢原子可以被如上所定义的卤原子替代,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基和五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、CH2-C2F5、CF2-C2F5、CF(CF3)2、1-氟甲基-2-氟乙基、1-氯甲基-2-氯乙基、1-溴甲基-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基等等。
术语“C3-C8环烷基”是指具有3-8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、环庚基或环辛基。
术语“C3-C8环烷基-C1-C4烷基”是指具有1-4个碳原子的烷基(如上所定义),其中该烷基的一个氢原子被具有3-8个碳原子的环烷基(如上所定义)替代。
术语“C1-C4烷氧基”是指经由氧在烷基中的任何位置键合的具有1-4个碳原子的直链或支化烷基,例如甲氧基、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-C4卤代烷氧基”是指如上所定义的C1-C4烷氧基,其中这些基团中的部分或所有氢原子可以被上述卤原子替代,例如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-氟丁氧基、4-溴丁氧基或九氟丁氧基。
术语“苯基-C1-C4烷基”是指具有1-4个碳原子的烷基(如上所定义),其中该烷基的一个氢原子被苯基替代。同样,术语“苯基-C2-C4链烯基”和“苯基-C2-C4炔基”分别是指链烯基和炔基,其中上述基团的一个氢原子被苯基替代。
化合物I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,还有需要的话可以带有1-4个C1-C4烷基取代基和/或一个苯基或苄基取代基的铵离子,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。它们可以通过使式I化合物与相应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式I化合物可以以由绕不对称基团的单键旋转受阻而出现的旋转异构体存在。它们也形成本发明主题的一部分。
取决于取代方式,式I化合物及其N-氧化物可以具有一个或多个手性中心,此时它们作为纯对映体或纯非对映体或者作为对映体或非对映体混合物存在。纯对映体或非对映体及其混合物二者均为本发明主题。
就各变量而言,中间体的实施方案对应于化合物I的实施方案。
优选如下那些化合物I以及适用的话还有本文所提供的所有子式如I.A的化合物及中间体如化合物VIII、XII和XIII,其中取代基(如X1、X2、R1、R2、Ra和Rb)相互独立地或更优选组合地具有下列含义:
根据本发明,X1和X2独立地选自卤素。一个实施方案涉及其中X1为F或Cl,尤其是Cl的化合物I。
另一实施方案涉及其中X2为F或Cl,尤其是Cl的化合物I。
根据本发明,R1为C3-C8环烷基、C3-C8环烷基-C1-C4烷基、苯基、苯基-C1-C4烷基、苯基-C2-C4链烯基或苯基-C2-C4炔基,其中脂族结构部分未被取代或者带有1、2、3或至多最大可能数的相同或不同基团Ra,后者相互独立地选自卤素、CN、硝基、C1-C4烷氧基和C1-C4卤代烷氧基;以及其中环烷基和/或苯基结构部分未被取代或者带有1、2、3、4、5或至多最大数目的相同或不同基团Rb,后者相互独立地选自卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。
根据另一实施方案,R1为C3-C8环烷基,尤其是C3-C6环烷基。根据具体实施方案,R1为环丙基、环戊基或环己基,尤其是环丙基。根据一个实施方案,该环烷基未被取代;根据另一实施方案,该环烷基带有1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Rb,后者相互独立地选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。根据具体实施方案,R1为环丙基、1-Cl-环丙基、1-F-环丙基、1-CH3-环丙基或1-CN-环丙基。
根据另一实施方案,R1为C3-C8环烷基-C1-C4烷基,尤其是C3-C6环烷基-C1-C4烷基。根据一个实施方案,环烷基结构部分未被取代;根据另一实施方案,环烷基结构部分被1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Rb取代,后者相互独立地选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。根据一个实施方案,烷基结构部分未被取代;根据另一实施方案,烷基结构部分被1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Ra取代,后者相互独立地选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
另一实施方案涉及其中R1为C3-C6环烷基或C3-C6环烷基-C1-C4烷基,更优选选自环丙基和环丙基甲基的化合物I,其中上述基团可以被如上所定义的Ra和/或Rb取代。
根据另一实施方案,R1为苯基。根据一个实施方案,苯基未被取代;根据另一实施方案,苯基被1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Rb取代,后者相互独立地选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。
另一实施方案涉及其中R1为苯基的化合物I,其中上述基团可以被如上所定义的Rb取代,更优选所述苯基带有1、2或3个卤素取代基,尤其是选自Cl和F的取代基。
另一实施方案涉及其中R1为苯基-C1-C4烷基、苯基-C2-C4链烯基或苯基-C2-C4炔基,更优选苄基、苯基乙烯基和苯基乙炔基,R1尤其为苄基的化合物I,其中上述基团可以被如上所定义的Ra和/或Rb取代。
根据另一实施方案,R1为苯基-C1-C4烷基,尤其是苯基-C1-C2烷基。根据一个实施方案,苯基结构部分未被取代;根据另一实施方案,苯基结构部分被1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Rb取代,后者相互独立地选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。根据一个实施方案,烷基结构部分未被取代;根据另一实施方案,烷基结构部分被1、2、3、4或5个,尤其是1、2或3个相同或不同的基团Ra取代,后者相互独立地选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
另一实施方案涉及其中R1未被取代的化合物I。
根据本发明,R2为C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C8环烷基、C3-C8环烷基-C1-C4烷基、苯基、苯基-C1-C4烷基、苯基-C2-C4链烯基或苯基-C2-C4炔基;其中脂族结构部分未被取代或者带有1、2、3或至多最大可能数的相同或不同基团Ra,Ra相互独立地选自卤素、CN、硝基、C1-C4烷氧基和C1-C4卤代烷氧基;并且其中R2的环烷基和/或苯基结构部分可以带有1、2、3、4、5或至多最大数目的相同或不同基团Rb,Rb相互独立地选自卤素、CN、硝基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。
根据一个实施方案,R2为C1-C6烷基,尤其是C1-C4烷基。具体实施方案涉及其中R2为甲基、乙基或异丙基的化合物。根据一个实施方案,烷基未被取代;根据另一实施方案,烷基带有1、2、3、4、5或6个,尤其是1、2、3或4个Ra,其中Ra选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
根据另一实施方案,R2为C2-C6链烯基,尤其是C2-C4链烯基。具体实施方案涉及其中R2为烯丙基的化合物。根据一个实施方案,链烯基未被取代;根据另一实施方案,链烯基带有1、2、3、4、5或6个,尤其是1、2、3或4个Ra,其中Ra选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
根据另一实施方案,R2为C2-C6炔基,尤其是C2-C4炔基。具体实施方案涉及其中R2为炔丙基的化合物。根据一个实施方案,炔基未被取代;根据另一实施方案,炔基带有1、2、3、4、5或6个,尤其是1、2、3或4个Ra,其中Ra选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
另一实施方案涉及其中R2为C1-C4烷基、C2-C4链烯基、C2-C4炔基、环丙基、环丙基甲基、苯基、苄基、苯基乙烯基或苯基乙炔基的化合物I,其中上述基团可以被如上所定义的Ra和/或Rb取代,更优选它们带有1、2或3个卤素取代基,甚至更优选R2为C1-C2卤代烷基,R2尤其为CF3。
另一实施方案涉及其中R2为C1-C4烷基、C2-C4链烯基、C2-C4炔基、环丙基、环丙基甲基、苯基、苄基、苯基乙烯基或苯基乙炔基,更优选C1-C4烷基,尤其是甲基的化合物I。
根据另一实施方案,R2为C3-C8环烷基,尤其是C3-C6环烷基。具体实施方案涉及其中R2环丙基的化合物。根据一个实施方案,环烷基未被取代;根据另一实施方案,环烷基带有1、2、3、4、5或6个,尤其是1、2、3或4个Rb,其中Rb选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。
根据另一实施方案,R2为C3-C8环烷基-C1-C4烷基,尤其是C3-C6环烷基-C1-C4烷基。具体实施方案涉及其中R2为环丙基甲基的化合物。根据一个实施方案,环烷基结构部分未被取代;根据另一实施方案,环烷基结构部分带有1、2、3、4、5或6个,尤其是1、2、3或4个Rb,其中Rb选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。根据另一实施方案,烷基结构部分未被取代;根据另一实施方案,烷基结构部分带有1、2、3、4、5或6个,尤其是1、2、3或4个Ra,其中Ra选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。
另一实施方案涉及其中R2为C3-C8环烷基或C3-C8环烷基-C1-C4烷基,更优选选自环丙基和环丙基甲基的化合物I,其中上述基团可以被如上所定义的Ra和/或Rb取代。
根据另一实施方案,R2为苯基。根据一个实施方案,苯基未被取代;根据另一实施方案,苯基带有1、2、3、4或5个,尤其是1、2或3个Rb,其中Rb选自F、Cl、Br、CN、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。
根据另一实施方案,R2为苯基-C1-C4烷基,尤其是苯基-C1-C2烷基,具体为苄基。根据一个实施方案,苯基结构部分未被取代;根据另一实施方案,苯基结构部分带有1、2、3、4或5个,尤其是1、2或3个Rb,其中Rb选自F、Cl、Br、CN、硝基、C1-C2烷基、C1-C2烷氧基、C1-C2卤代烷基和C1-C2卤代烷氧基。根据另一实施方案,烷基结构部分未被取代;根据另一实施方案,烷基结构部分带有1、2、3、4或5个,尤其是1、2或3个Ra,其中Ra选自F、Cl、Br、CN、C1-C2烷氧基和C1-C2卤代烷氧基。另一实施方案涉及其中R2未被取代的化合物I。
另一实施方案涉及其中X1和X2均为Cl且R1为未被取代的苄基的化合物,该类化合物具有式I.A:
另一实施方案涉及其中X1和X2均为Cl且R1为未被取代的环丙基的化合物,该类化合物具有式I.B:
本发明的特别优选实施方案涉及其中X1、X2和R1(包括Ra、Rb)的组合如下表P所定义的化合物I。
表P:
熟练技术人员容易理解就化合物I所给优选情形相应地适用于如上所定义的式XII。
对于其用途,特别优选汇编在下表1-84、表84a-84w、表85-168和表168a-168w中的式I化合物1-3240和1a-3240a。此外,在表中对取代基提到的基团为所述取代基的特别优选实施方案,与其中提到它们的组合无关。
表1:其中X1、X2和R1如表P的P-1行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1-30。
表2:其中X1、X2和R1如表P的P-2行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物31-60。
表3:其中X1、X2和R1如表P的P-3行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物61-90。
表4:其中X1、X2和R1如表P的P-4行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物91-120。
表5:其中X1、X2和R1如表P的P-5行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物121-150。
表6:其中X1、X2和R1如表P的P-6行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物151-180。
表7:其中X1、X2和R1如表P的P-7行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物181-210。
表8:其中X1、X2和R1如表P的P-8行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物211-240。
表9:其中X1、X2和R1如表P的P-9行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物241-270。
表10:其中X1、X2和R1如表P的P-10行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物271-300。
表11:其中X1、X2和R1如表P的P-11行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物301-330。
表12:其中X1、X2和R1如表P的P-12行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物331-360。
表13:其中X1、X2和R1如表P的P-13行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物361-390。
表14:其中X1、X2和R1如表P的P-14行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物391-420。
表15:其中X1、X2和R1如表P的P-15行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物421-450。
表16:其中X1、X2和R1如表P的P-16行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物451-480。
表17:其中X1、X2和R1如表P的P-17行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物481-510。
表18:其中X1、X2和R1如表P的P-18行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物511-540。
表19:其中X1、X2和R1如表P的P-19行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物541-570。
表20:其中X1、X2和R1如表P的P-20行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物571-600。
表21:其中X1、X2和R1如表P的P-21行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物601-630。
表22:其中X1、X2和R1如表P的P-22行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物631-660。
表23:其中X1、X2和R1如表P的P-23行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物661-690。
表24:其中X1、X2和R1如表P的P-24行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物691-720。
表25:其中X1、X2和R1如表P的P-25行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物721-750。
表26:其中X1、X2和R1如表P的P-26行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物751-780。
表27:其中X1、X2和R1如表P的P-27行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物781-810。
表28:其中X1、X2和R1如表P的P-28行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物811-840。
表29:其中X1、X2和R1如表P的P-29行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物841-870。
表30:其中X1、X2和R1如表P的P-30行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物871-900。
表31:其中X1、X2和R1如表P的P-31行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物901-930。
表32:其中X1、X2和R1如表P的P-32行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物931-960。
表33:其中X1、X2和R1如表P的P-33行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物961-990。
表34:其中X1、X2和R1如表P的P-34行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物991-1020。
表35:其中X1、X2和R1如表P的P-35行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1021-1050。
表36:其中X1、X2和R1如表P的P-36行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1051-1080。
表37:其中X1、X2和R1如表P的P-37行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1081-1110。
表38:其中X1、X2和R1如表P的P-38行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1111-1140。
表39:其中X1、X2和R1如表P的P-39行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1141-1170。
表40:其中X1、X2和R1如表P的P-40行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1171-1200。
表41:其中X1、X2和R1如表P的P-41行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1201-1230。
表42:其中X1、X2和R1如表P的P-42行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1231-1260。
表43:其中X1、X2和R1如表P的P-43行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1261-1290。
表44:其中X1、X2和R1如表P的P-44行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1291-1320。
表45:其中X1、X2和R1如表P的P-45行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1321-1350。
表46:其中X1、X2和R1如表P的P-46行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1351-1380。
表47:其中X1、X2和R1如表P的P-47行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1381-1410。
表48:其中X1、X2和R1如表P的P-48行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1411-1440。
表49:其中X1、X2和R1如表P的P-49行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1441-1470。
表50:其中X1、X2和R1如表P的P-50行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1471-1500。
表51:其中X1、X2和R1如表P的P-51行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1501-1530。
表52:其中X1、X2和R1如表P的P-52行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1531-1560。
表53:其中X1、X2和R1如表P的P-53行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1561-1590。
表54:其中X1、X2和R1如表P的P-54行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1591-1620。
表55:其中X1、X2和R1如表P的P-55行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1621-1650。
表56:其中X1、X2和R1如表P的P-56行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1651-1680。
表57:其中X1、X2和R1如表P的P-57行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1681-1710。
表58:其中X1、X2和R1如表P的P-58行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1711-1740。
表59:其中X1、X2和R1如表P的P-59行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1741-1770。
表60:其中X1、X2和R1如表P的P-60行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1771-1800。
表61:其中X1、X2和R1如表P的P-61行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1801-1830。
表62:其中X1、X2和R1如表P的P-62行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1831-1860。
表63:其中X1、X2和R1如表P的P-63行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1861-1890。
表64:其中X1、X2和R1如表P的P-64行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1891-1920。
表65:其中X1、X2和R1如表P的P-65行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1921-1950。
表66:其中X1、X2和R1如表P的P-66行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1951-1980。
表67:其中X1、X2和R1如表P的P-67行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物1981-2010。
表68:其中X1、X2和R1如表P的P-68行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2011-2040。
表69:其中X1、X2和R1如表P的P-69行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2041-2070。
表70:其中X1、X2和R1如表P的P-70行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2071-2100。
表71:其中X1、X2和R1如表P的P-71行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2101-2130。
表72:其中X1、X2和R1如表P的P-72行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2131-2160。
表73:其中X1、X2和R1如表P的P-73行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2161-2190。
表74:其中X1、X2和R1如表P的P-74行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2191-2220。
表75:其中X1、X2和R1如表P的P-75行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2221-2250。
表76:其中X1、X2和R1如表P的P-76行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2251-2280。
表77:其中X1、X2和R1如表P的P-77行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2281-2310。
表78:其中X1、X2和R1如表P的P-78行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2311-2340。
表79:其中X1、X2和R1如表P的P-79行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2341-2370。
表80:其中X1、X2和R1如表P的P-80行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2371-2400。
表81:其中X1、X2和R1如表P的P-81行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2401-2430。
表82:其中X1、X2和R1如表P的P-82行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2431-2460。
表83:其中X1、X2和R1如表P的P-83行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2461-2490。
表84:其中X1、X2和R1如表P的P-84行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2491-2520。
表84a:其中X1、X2和R1如表P的P-85行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2521-2550。
表84b:其中X1、X2和R1如表P的P-86行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2551-2580。
表84c:其中X1、X2和R1如表P的P-87行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2581-2610。
表84d:其中X1、X2和R1如表P的P-88行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2611-2640。
表84e:其中X1、X2和R1如表P的P-89行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2641-2670。
表84f:其中X1、X2和R1如表P的P-90行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2671-2700。
表84g:其中X1、X2和R1如表P的P-91行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2701-2730。
表84:其中X1、X2和R1如表P的P-92行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2731-2760。
表84h:其中X1、X2和R1如表P的P-93行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2761-2790。
表84i:其中X1、X2和R1如表P的P-94行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2791-2820。
表84j:其中X1、X2和R1如表P的P-95行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2821-2850。
表84k:其中X1、X2和R1如表P的P-96行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2851-2880。
表84l:其中X1、X2和R1如表P的P-97行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2881-2910。
表84m:其中X1、X2和R1如表P的P-98行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2911-2940。
表84n:其中X1、X2和R1如表P的P-99行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2941-2970。
表84o:其中X1、X2和R1如表P的P-100行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物2971-3000。
表84p:其中X1、X2和R1如表P的P-101行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3001-3030。
表84q:其中X1、X2和R1如表P的P-102行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3031-3060。
表84r:其中X1、X2和R1如表P的P-103行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3061-3090。
表84s:其中X1、X2和R1如表P的P-104行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3091-3120。
表84t:其中X1、X2和R1如表P的P-105行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3121-3150。
表84u:其中X1、X2和R1如表P的P-106行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3151-3180。
表84v:其中X1、X2和R1如表P的P-107行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3181-3210。
表84w:其中X1、X2和R1如表P的P-108行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A的一行的式I化合物3211-3240。
表85:其中X1、X2和R1如表P的P-1行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1a-30a。
表86:其中X1、X2和R1如表P的P-2行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物31a-60a。
表87:其中X1、X2和R1如表P的P-3行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物61a-90a。
表88:其中X1、X2和R1如表P的P-4行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物91a-120a。
表89:其中X1、X2和R1如表P的P-5行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物121a-150a。
表90:其中X1、X2和R1如表P的P-6行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物151a-180a。
表91:其中X1、X2和R1如表P的P-7行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物181a-210a。
表92:其中X1、X2和R1如表P的P-8行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物211a-240a。
表93:其中X1、X2和R1如表P的P-9行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物241a-270a。
表94:其中X1、X2和R1如表P的P-10行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物271a-300a。
表95:其中X1、X2和R1如表P的P-11行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物301a-330a。
表96:其中X1、X2和R1如表P的P-12行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物331a-360a。
表97:其中X1、X2和R1如表P的P-13行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物361a-390a。
表98:其中X1、X2和R1如表P的P-14行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物391a-420a。
表99:其中X1、X2和R1如表P的P-15行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物421a-450a。
表100:其中X1、X2和R1如表P的P-16行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物451a-480a。
表101:其中X1、X2和R1如表P的P-17行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物481a-510a。
表102:其中X1、X2和R1如表P的P-18行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物511a-540a。
表103:其中X1、X2和R1如表P的P-19行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物541a-570a。
表104:其中X1、X2和R1如表P的P-20行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物571a-600a。
表105:其中X1、X2和R1如表P的P-21行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物601a-630a。
表106:其中X1、X2和R1如表P的P-22行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物631a-660a。
表107:其中X1、X2和R1如表P的P-23行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物661a-690a。
表108:其中X1、X2和R1如表P的P-24行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物691a-720a。
表109:其中X1、X2和R1如表P的P-25行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物721a-750a。
表110:其中X1、X2和R1如表P的P-26行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物751a-780a。
表111:其中X1、X2和R1如表P的P-27行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物781a-810a。
表112:其中X1、X2和R1如表P的P-28行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物811a-840a。
表113:其中X1、X2和R1如表P的P-29行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物841a-870a。
表114:其中X1、X2和R1如表P的P-30行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物871a-900a。
表115:其中X1、X2和R1如表P的P-31行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物901a-930a。
表116:其中X1、X2和R1如表P的P-32行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物931a-960a。
表117:其中X1、X2和R1如表P的P-33行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物961a-990a。
表118:其中X1、X2和R1如表P的P-34行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物991a-1020a。
表119:其中X1、X2和R1如表P的P-35行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1021a-1050a。
表120:其中X1、X2和R1如表P的P-36行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1051a-1080a。
表121:其中X1、X2和R1如表P的P-37行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1081a-1110a。
表122:其中X1、X2和R1如表P的P-38行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1111a-1140a。
表123:其中X1、X2和R1如表P的P-39行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1141a-1170a。
表124:其中X1、X2和R1如表P的P-40行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1171a-1200a。
表125:其中X1、X2和R1如表P的P-41行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1201a-1230a。
表126:其中X1、X2和R1如表P的P-42行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1231a-1260a。
表127:其中X1、X2和R1如表P的P-43行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1261a-1290a。
表128:其中X1、X2和R1如表P的P-44行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1291a-1320a。
表129:其中X1、X2和R1如表P的P-45行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1321a-1350a。
表130:其中X1、X2和R1如表P的P-46行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1351a-1380a。
表131:其中X1、X2和R1如表P的P-47行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1381a-1410a。
表132:其中X1、X2和R1如表P的P-48行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1411a-1440a。
表133:其中X1、X2和R1如表P的P-49行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1441a-1470a。
表134:其中X1、X2和R1如表P的P-50行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1471a-1500a。
表135:其中X1、X2和R1如表P的P-51行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1501a-1530a。
表136:其中X1、X2和R1如表P的P-52行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1531a-1560a。
表137:其中X1、X2和R1如表P的P-53行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1561a-1590a。
表138:其中X1、X2和R1如表P的P-54行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1591a-1620a。
表139:其中X1、X2和R1如表P的P-55行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1621a-1650a。
表140:其中X1、X2和R1如表P的P-56行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1651a-1680a。
表141:其中X1、X2和R1如表P的P-57行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1681a-1710a。
表142:其中X1、X2和R1如表P的P-58行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1711a-1740a。
表143:其中X1、X2和R1如表P的P-59行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1741a-1770a。
表144:其中X1、X2和R1如表P的P-60行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1771a-1800a。
表145:其中X1、X2和R1如表P的P-61行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1801a-1830a。
表146:其中X1、X2和R1如表P的P-62行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1831a-1860a。
表147:其中X1、X2和R1如表P的P-63行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1861a-1890a。
表148:其中X1、X2和R1如表P的P-64行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1891a-1920a。
表149:其中X1、X2和R1如表P的P-65行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1921a-1950a。
表150:其中X1、X2和R1如表P的P-66行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1951a-1980a。
表151:其中X1、X2和R1如表P的P-67行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物1981a-2010a。
表152:其中X1、X2和R1如表P的P-68行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2011a-2040a。
表153:其中X1、X2和R1如表P的P-69行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2041a-2070a。
表154:其中X1、X2和R1如表P的P-70行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2071a-2100a。
表155:其中X1、X2和R1如表P的P-71行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2101a-2130a。
表156:其中X1、X2和R1如表P的P-72行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2131a-2160a。
表157:其中X1、X2和R1如表P的P-73行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2161a-2190a。
表158:其中X1、X2和R1如表P的P-74行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2191a-2220a。
表159:其中X1、X2和R1如表P的P-75行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2221a-2250a。
表160:其中X1、X2和R1如表P的P-76行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2251a-2280a。
表161:其中X1、X2和R1如表P的P-77行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2281a-2310a。
表162:其中X1、X2和R1如表P的P-78行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2311a-2340a。
表163:其中X1、X2和R1如表P的P-79行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2341a-2370a。
表164:其中X1、X2和R1如表P的P-80行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2371a-2400a。
表165:其中X1、X2和R1如表P的P-81行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2401a-2430a。
表166:其中X1、X2和R1如表P的P-82行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2431a-2460a。
表167:其中X1、X2和R1如表P的P-83行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2461a-2490a。
表168:其中X1、X2和R1如表P的P-84行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2491a-2520a。
表168a:其中X1、X2和R1如表P的P-85行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2521a-2550a。
表168b:其中X1、X2和R1如表P的P-86行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2551a-2580a。
表168c:其中X1、X2和R1如表P的P-87行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2581a-2610a。
表168d:其中X1、X2和R1如表P的P-88行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2611a-2640a。
表168e:其中X1、X2和R1如表P的P-89行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2641a-2670a。
表168f:其中X1、X2和R1如表P的P-90行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2671a-2700a。
表168g:其中X1、X2和R1如表P的P-91行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2701a-2730a。
表168:其中X1、X2和R1如表P的P-92行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2731a-2760a。
表168h:其中X1、X2和R1如表P的P-93行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2761a-2790a。
表168i:其中X1、X2和R1如表P的P-94行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2791a-2820a。
表168j:其中X1、X2和R1如表P的P-95行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2821a-2850a。
表168k:其中X1、X2和R1如表P的P-96行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2851a-2880a。
表168l:其中X1、X2和R1如表P的P-97行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2881a-2910a。
表168m:其中X1、X2和R1如表P的P-98行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2911a-2940a。
表168n:其中X1、X2和R1如表P的P-99行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2941a-2970a。
表168o:其中X1、X2和R1如表P的P-100行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物2971a-3000a。
表168p:其中X1、X2和R1如表P的P-101行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3001a-3030a。
表168q:其中X1、X2和R1如表P的P-102行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3031a-3060a。
表168r:其中X1、X2和R1如表P的P-103行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3061a-3090a。
表168s:其中X1、X2和R1如表P的P-104行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3091a-3120a。
表168t:其中X1、X2和R1如表P的P-105行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3121a-3150a。
表168u:其中X1、X2和R1如表P的P-106行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3151a-3180a。
表168v:其中X1、X2和R1如表P的P-107行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3181a-3210a。
表168w:其中X1、X2和R1如表P的P-108行所定义且R2的含义对各单独化合物而言在每种情况下对应于表A1的一行的式I化合物3211a-3240a。
表A:
表A1:
本发明化合物I和VIII以及组合物分别适合作为杀真菌剂。它们的特征在于对宽范围的植物病原性真菌[包括尤其源于根肿菌纲(Plasmodiophoromycetes)、Peronosporomycetes(同义词卵菌纲(Oomycetes))、壶菌纲(Chytridiomycetes)、接合菌纲(Zygomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)和半知菌纲(Deuteromycetes)(同义词不完全菌纲(Fungi imperfecti))的土传真菌]具有显著的效力。它们中的一些内吸有效并且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。此外,它们适合防治尤其发生在木材或植物根部的有害真菌。
本发明化合物I和VIII以及组合物特别对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,如仁果、核果或浆果,例如苹果、梨、李、桃、杏仁、樱桃、草莓、悬钩子、黑莓或鹅莓;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,例如南瓜、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,例如针叶树,以及植物繁殖材料如种子和这些植物的作物材料中防治大量植物病原性真菌特别重要。
优选化合物I和VIII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、菜豆或南瓜上防治大量真菌。
术语“植物繁殖材料”应理解为表示植物的所有繁殖部分如种子,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。这些幼苗还可以在移植之前通过经由浸渍或浇灌的完全或部分处理而保护。
优选分别将化合物I和VIII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、棉花和大豆上防治大量真菌。
术语“栽培植物”应理解为包括已经通过育种、诱变或基因工程修饰的植物,包括但不限于上市销售或开发的农业生物技术产品(参见http://www.bio.org/speeches/pubs/er/agri_products.asp)。基因修饰植物是其基因材料通过使用在自然条件下不易通过杂交、突变或自然重组得到的重组DNA技术修饰的植物。通常将一个或多个基因整合到基因修饰植物的遗传材料中以改善植物的某些性能。这类基因修饰还包括但不限于蛋白质、寡肽或多肽的靶向翻译后修饰,例如通过糖基化或聚合物加成如异戊二烯化、乙酰化或法呢基化结构部分或PEG结构部分。
通过育种、诱变或基因工程修饰的植物例如因常规育种或基因工程方法而耐受特殊类别除草剂的施用,这些除草剂如植物生长素除草剂如麦草畏(dicamba)或2,4-D;漂白剂除草剂如羟基苯基丙酮酸二加氧酶(HPPD)抑制剂或八氢番茄红素去饱和酶(PDS)抑制剂;乙酰乳酸合成酶(ALS)抑制剂,例如磺酰脲类或咪唑啉酮类;烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂,例如草甘膦(glyphosate);谷氨酰胺合成酶(GS)抑制剂,例如草铵膦(glufosinate);原卟啉原-IX氧化酶抑制剂;类脂生物合成抑制剂如乙酰基CoA羧化酶(ACCase)抑制剂;或oxynil(即溴苯腈(bromoxynil)或碘苯腈(ioxynil))除草剂;此外,植物已经通过多次基因修饰而耐受多种类别除草剂,如耐受草甘膦和草铵膦二者或耐受草甘膦和选自ALS抑制剂、HPPD抑制剂、植物生长素抑制剂或ACCase抑制剂的另一类别除草剂二者。这些除草剂耐受性技术例如描述于Pest Managem.Sci.61,2005,246;61,2005,258;61,2005,277;61,2005,269;61,2005,286;64,2008,326;64,2008,332;Weed Sci.57,2009,108;Austral.J.Agricult.Res.58,2007,708;Science316,2007,1185;以及其中引用的文献中。几种栽培植物已经通过常规育种方法(诱变)耐受除草剂,例如耐受咪唑啉酮类如咪草啶酸(imazamox)的夏播油菜(Canola,德国BASF SE)或耐受磺酰脲类,例如苯黄隆(tribenuron)的向日葵(DuPont,USA)。已经使用基因工程方法来赋予栽培植物如大豆、棉花、玉米、甜菜和油菜对除草剂如草甘膦和草铵膦的耐受性,它们中的一些可以以商标名(耐受草甘膦,Monsanto,U.S.A.)、(耐受咪唑啉酮,德国BASF SE)和(耐受草铵膦,德国BayerCropScience)市购。
此外,还包括通过使用重组DNA技术而能够合成一种或多种杀虫蛋白,尤其是由芽孢杆菌属(Bacillus)细菌,特别是苏云金芽孢杆菌(Bacillus thuringiensis)已知的那些的植物,所述杀虫蛋白如δ-内毒素,例如CryIA(b),CryIA(c),CryIF,CryIF(a2),CryIIA(b),CryIIIA,CryIIIB(b1)或Cry9c;无性杀虫蛋白(VIP),例如VIP1、VIP2、VIP3或VIP3A;线虫定居细菌的杀虫蛋白,例如发光杆菌属(Photorhabdus)或致病杆菌属(Xenorhabdus);动物产生的毒素如蝎子毒素、蜘蛛毒素、黄蜂毒素或其他昆虫特异性神经毒素;真菌产生的毒素,例如链霉菌属(Streptomycetes)毒素;植物凝集素,例如豌豆或大麦凝集素;凝集素;蛋白酶抑制剂,例如胰蛋白酶抑制剂,丝氨酸蛋白酶抑制剂,patatin,半胱氨酸蛋白酶抑制剂或木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),例如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白、皂草素或异株腹泻毒蛋白(bryodin);类固醇代谢酶,例如3-羟基类固醇氧化酶、蜕皮甾类-IDP糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂,例如钠通道或钙通道阻断剂;保幼激素酯酶;利尿激素受体(helicokinin受体);合成酶,联苄合成酶,壳多糖酶或葡聚糖酶。在本发明上下文中,这些杀虫蛋白或毒素还具体理解为前毒素、杂合蛋白、截短的或其他方面改性的蛋白。杂合蛋白的特征在于蛋白域的新型组合(例如参见WO2002/015701)。该类毒素或能够合成这些毒素的基因修饰植物的其他实例公开于EP-A374753、WO93/07278、WO95/34656、EP-A427529、EP-A451878、WO03/18810和WO03/52073中。生产这些基因修饰植物的方法通常对本领域熟练技术人员是已知的且例如描述于上述出版物中。这些含于基因修饰植物中的杀虫蛋白赋予产生这些蛋白的植物以对所有分类学上为节肢动物的害虫,尤其是甲虫(鞘翅目(Coeleropta))、双翅目昆虫(双翅目(Diptera))和蛾(鳞翅目(Lepidoptera))以及线虫(线虫纲(Nematoda))的耐受性。能够合成一种或多种杀虫蛋白的基因修饰植物例如描述于上述出版物中,它们中的一些可市购,例如(产生毒素Cry1Ab的玉米品种),Plus(产生毒素CrylAb和Cry3Bd1的玉米品种),(产生毒素Cry9c的玉米品种),RW(产生Cry34Ab1、Cry35Ab1和酶膦丝菌素-N-乙酰转移酶[PAT]的玉米品种);33B(产生毒素Cry1Ac的棉花品种),I(产生毒素Cry1Ac的棉花品种),II(产生毒素Cry1Ac和Cry2Ab2的棉花品种);(产生VIP毒素的棉花品种);(产生毒素Cry3A的土豆品种); Bt11(例如CB)和法国SyngentaSeeds SAS的Bt176(产生毒素Cry1Ab和PAT酶的玉米品种),法国Syngenta Seeds SAS的MIR604(产生毒素Cry3A的修饰译本的玉米品种,参见WO03/018810),比利时MonsantoEurope S.A.的MON863(产生毒素Cry3Bb1的玉米品种),比利时Monsanto Europe S.A.的IPC531(产生毒素Cry1Ac的修饰译本的棉花品种)和比利时Pioneer OverseasCorporation的1507(产生毒素Cry1F和PAT酶的玉米品种)。
此外,还包括通过使用重组DNA技术能够合成一种或多种对细菌、病毒或真菌病原体的抗性或耐受性增强的蛋白质的植物。该类蛋白的实例是所谓的“与发病机理相关的蛋白”(PR蛋白,例如参见EP-A0392225),植物病害抗性基因(例如表达针对来自墨西哥野生土豆Solanum bulbocastanum的致病疫霉(Phytophthora infestans)起作用的抗性基因的土豆品种)或T4溶菌酶(例如能够合成对细菌如Erwinia amylvora具有增强的抗性的这些蛋白的土豆品种)。生产这些基因修饰植物的方法通常对本领域熟练技术人员是已知的且例如描述于上述出版物中。
此外,还包括通过使用重组DNA技术能够合成一种或多种蛋白以提高产量(例如生物质产生、谷粒产量、淀粉含量、油含量或蛋白质含量),对干旱、盐或其他生长限制性环境因素的耐受性或对害虫以及真菌、细菌和病毒病原体的耐受性的植物。
此外,还包括通过使用重组DNA技术而含有改变量的物质含量或新物质含量以尤其改善人类或动物营养的植物,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油料作物(例如油菜,加拿大DOWAgro Sciences)。
此外,还包括通过使用重组DNA技术而含有改变量的物质含量或新物质含量以尤其改善原料生产的植物,例如产生增加量的支链淀粉的土豆(例如土豆,德国BASF SE)。
化合物I和VIII及其组合物分别特别适合防治下列植物病害: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、油菜(例如芸苔生链格孢(A.brassicola)或芸苔链格孢(A.brassicae))、糖用甜菜(例如A.tenuis)、水果、稻、大豆、土豆(例如早疫链格孢(A.solani)或链格孢(A.alternata))、西红柿(例如早疫链格孢或链格孢)和小麦上的链格孢属(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);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)、油菜、花卉、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(Bremialactucae)(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);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))和大豆(例如大豆炭疽病菌(C.truncatum)或毛豆炭疽病菌(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C.oleaginum;果树、葡萄藤(例如C.liriodendri,有性型:Neonectria liriodendri:乌脚病)和观赏树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)、F.mediterranea、Phaeomoniellachlamydospora(旧名为Phaeoacremonium chlamydosporum)、Phaeoacremoniumaleophilum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(Entyloma oryzae)(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、黑星病和银尖病),西红柿上的尖镰孢(F.oxysporum),大豆上的茄镰孢(F.solani)和玉米上的轮枝镰孢(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(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: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)(Sigatoka黑斑病);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(Phomalingam)(根腐病和茎腐病)以及糖用甜菜上的甜菜茎点霉(P.betae)(根腐病、叶斑病和立枯疡);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: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,茎腐病和果树腐烂病);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、仁果和浆果上的叉丝单囊壳属(Podosphaera)(白粉病),例如苹果上的苹果白粉病菌(P.leucotricha);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(Pseudocercosporella herpotrichoides)(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P.kuehnii(橙锈病)和芦笋上的天门冬属柄锈病(P.asparagi);小麦上的小麦黄斑叶枯病菌(Pyrenophora(无性型:Drechslera)tritici-repentis)(黄斑病)或大麦上的大麦网斑内脐蠕孢(P.teres)(网斑病);梨孢属(Pyricularia),例如稻上的稻瘟病菌(P.oryzae)(有性型:Magnaporthegrisea,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))上的腐霉属(Pythium)(立枯病);柱隔孢属(Ramularia),例如大麦上的R.collo-cygni(柱隔孢叶斑病,生理叶斑病)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R.solani(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)(叶斑病);稻上的稻帚枝霉(Sarocladium oryzae)和S.attenuatum(叶鞘腐败病);蔬菜和大田作物如油菜、向日葵(例如核盘菌(S.sclerotiorum))和大豆(例如S.rolfsii或大豆菌核病(S.sclerotiorum))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)(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: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):丝黑穗病)、小米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)(白粉病);土豆上的粉痂菌(Spongosporasubterranea)(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));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Chalaraelegans);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T.tritici(同义词T.caries,小麦腥黑穗病)和T.controversa(矮腥黑穗病);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)和糖用甜菜(例如甜菜锈病菌(U.betae))上的单孢锈属(Uromyces)(锈病);禾谷类(例如麦散黑粉菌(U.nuda)和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),例如草莓、油菜、土豆和西红柿上的茄黄萎病菌(V.dahliae)。
化合物I和VIII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真菌。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、纸张和纸板、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。对于木材和其他材料的保护,特别应注意下列有害真菌:子囊菌纲真菌,例如线嘴壳属,长喙壳属,出芽短梗霉(Aureobasidium pullulans),Sclerophoma spp.,毛壳属(Chaetomium spp.),腐质霉属(Humicola spp.),彼得壳属(Petriella spp.),毛束霉属(Trichurus spp.);担子菌纲真菌,例如粉孢革菌属(Coniophora spp.),革盖菌属(Coriolus spp.),粘褶菌属(Gloeophyllum spp.),香菇属(Lentinus spp.),侧耳属(Pleurotus spp.),卧孔属(Poria spp.),干朽菌属(Serpulaspp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,例如曲霉属(Aspergillus spp.),枝孢属,青霉属(Penicillium spp.),木霉属(Trichoderma spp.),链格孢属,拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,例如毛霉属(Mucor spp.),此外在储存产品和收获产品的保护中应注意下列酵母真菌:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I和VIII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或VIII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)和对生命和/或非生命应力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。
式I和VIII化合物可以以其生物学活性可能不同的不同晶型存在。它们同样为本发明的主题。
化合物I和VIII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或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。
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或VIII本身或包含至少一种化合物I或VIII的组合物预防性地处理。
本发明还涉及包含助剂和至少一种本发明化合物I或VIII的农化组合物。
农化组合物包含杀真菌有效量的化合物I或VIII。术语“有效量”表示足以在栽培植物上或在材料保护中防治有害真菌且不对被处理植物引起显著损害的量的本发明组合物或化合物I或VII。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、被处理的栽培植物或材料、气候条件以及所用具体化合物I或VIII。
化合物I和VIII、其N-氧化物和盐可以转化成农化组合物常用的类型,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。组合物类型的实例是悬浮液(SC、OD、FS),可乳化浓缩物(EC),乳液(EW、EO、ES、ME),胶囊(例如CS、ZC),糊,锭剂,可湿性粉末或粉剂(WP、SP、WS、DP、DS),模压品(例如BR、TB、DT),颗粒(例如WG、SG、GR、FG、GG、MG),杀虫制品(例如LN)以及处理植物繁殖材料如种子的凝胶配制剂(例如GF)。这些和其他组合物类型在“Catalogue of pesticide formulation types and international codingsystem”,Technical Monograph,第2期,2008年5月第6版,CropLife International中有定义。
组合物如Mollet和Grubemann,Formulation technology,Wiley VCH,Weinheim,2001;或Knowles,New developments in crop protection product formulation,AgrowReports DS243,T&F Informa,London,2005所述以已知方式制备。
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、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物质,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和油的硫酸盐、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和异噻唑啉酮衍生物如烷基异噻唑啉酮和苯并异噻唑啉酮。
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。
组合物类型及其制备的实例为:
i)水溶性浓缩物(SL,LS)
将10-60重量%化合物I和VIII和5-15重量%润湿剂(例如醇烷氧基化物)溶于加至100重量%的水和/或水溶性溶剂(例如醇)中。活性物质在用水稀释时溶解。
ii)分散性浓缩物(DC)
将5-25重量%化合物I或VIII和1-10重量%分散剂(例如聚乙烯吡咯烷酮)溶于加至100重量%的有机溶剂(例如环己酮)中。用水稀释得到分散体。
iii)可乳化浓缩物(EC)
将15-70重量%化合物I或VIII和5-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于加至100重量%的水不溶性有机溶剂(例如芳族烃)中。用水稀释得到乳液。
iv)乳液(EW,EO,ES)
将5-40重量%化合物I或VIII和1-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于20-40重量%水不溶性有机溶剂(例如芳族烃)中。借助乳化机将该混合物引入加至100重量%的水中并制成均相乳液。用水稀释得到乳液。
v)悬浮液(SC,OD,FS)
在搅拌的球磨机中将20-60重量%化合物I或VIII在加入2-10重量%分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)、0.1-2重量%增稠剂(例如黄原胶)和加至100重量%的水下粉碎,得到细碎活性物质悬浮液。用水稀释得到稳定的活性物质悬浮液。对于FS类型组合物加入至多40重量%粘合剂(例如聚乙烯醇)。
vi)水分散性颗粒和水溶性颗粒(WG,SG)
在加入加至100重量%的分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)下精细研磨50-80重量%化合物I或VIII并借助工业装置(例如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性物质分散体或溶液。
vii)水分散性粉末和水溶性粉末(WP,SP,WS)
将50-80重量%化合物I或VIII在加入1-5重量%分散剂(例如木素磺酸钠)、1-3重量%润湿剂(例如醇乙氧基化物)和加至100重量%的固体载体(例如硅胶)下在转子-定子磨机中研磨。用水稀释得到稳定的活性物质分散体或溶液。
viii)凝胶(GW,GF)
在搅拌的球磨机中在加入3-10重量%分散剂(例如木素磺酸钠)、1-5重量%增稠剂(例如羧甲基纤维素)和加至100重量%的水下粉碎5-25重量%化合物I或VIII,得到活性物质的精细悬浮液。用水稀释得到稳定的活性物质悬浮液。
iv)微乳液(ME)
将5-20重量%化合物I或VIII加入5-30重量%有机溶剂共混物(例如脂肪酸二甲基酰胺和环己酮)、10-25重量%表面活性剂共混物(例如醇乙氧基化物和芳基酚乙氧基化物)和加至100重量%的水中。将该混合物搅拌1小时,以自发产生热力学稳定的微乳液。
iv)微胶囊(CS)
将包含5-50重量%化合物I或VIII、0-40重量%水不溶性有机溶剂(例如芳族烃)、2-15重量%丙烯酸系单体(例如甲基丙烯酸甲酯、甲基丙烯酸和二-或三丙烯酸酯)的油相分散到保护性胶体(例如聚乙烯醇)的水溶液中。由自由基引发剂引发的自由基聚合导致形成聚(甲基)丙烯酸酯微胶囊。或者将包含5-50重量%本发明化合物I、0-40重量%水不溶性有机溶剂(例如芳族烃)和异氰酸酯单体(例如二苯基甲烷-4,4’-二异氰酸酯)的油相分散到保护性胶体(例如聚乙烯醇)的水溶液中。加入多胺(例如六亚甲基二胺)导致形成聚脲微胶囊。单体量为1-10重量%。重量%涉及整个CS组合物。
ix)可撒粉粉末(DP,DS)
将1-10重量%化合物I或VIII细碎研磨并与加至100重量%的固体载体(例如细碎高岭土)充分混合。
x)颗粒(GR,FG)
将0.5-30重量%化合物I或VIII细碎研磨并结合加至100重量%的固体载体(例如硅酸盐)。通过挤出、喷雾干燥或流化床实现造粒。
xi)超低容量液体(UL)
将1-50重量%化合物I或VIII溶于加至100重量%的有机溶剂(例如芳族烃)中。
组合物类型i)-xi)可以任选包含其他助剂,如0.1-1重量%杀菌剂,5-15重量%防冻剂,0.1-1重量%消泡剂和0.1-1重量%着色剂。
农化组合物通常包含0.01-95重量%,优选0.1-90重量%,尤其是0.5-75重量%活性物质。活性物质以90-100%,优选95-100%的纯度(根据NMR光谱)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或VIII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繁殖材料的拌种、包衣、造粒、撒粉、浸泡和犁沟内施用方法。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VIII或其组合物分别施用于植物繁殖材料上。
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,特别优选0.05-0.9kg/ha,尤其是0.1-0.75kg/ha。
在植物繁殖材料如种子例如通过撒粉、包衣或浸透种子的处理中,通常要求活性物质的量为0.1-10000g/100kg,优选1-1000g/100kg,更优选1-100g/100kg,最优选5-100g/100kg植物繁殖材料(优选种子)。
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。
可以向活性物质或包含它们的组合物中作为预混物加入或者合适的话在紧临使用前加入(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(例如除草剂、杀虫剂、杀真菌剂、生长调节剂、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。
用户通常将本发明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。这里将该农化组合物用水、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化组合物。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。
根据一个实施方案,用户可以自己在喷雾罐中混合本发明组合物的各组分,例如成套包装的各部分或二元或三元混合物的各部分并且合适的话可以加入其他助剂。
将化合物I或VIII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。
化合物I或VIII可以与其一起使用的下列活性物质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(例如嗜球果伞素类):腈嘧菌酯(azoxystrobin)、甲香菌酯(coumethoxystrobin)、丁香菌酯(coumoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、烯肟菌胺(fenaminstrobin)、fenoxystrobin/氟菌螨酯(flufenoxystrobin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、pyrametostrobin、唑菌酯(pyraoxystrobin)、肟菌酯(trifloxystrobin)、2-[2-(2,5-二甲基苯氧基甲基)苯基]-3-甲氧基丙烯酸甲酯、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、pyribencarb、triclopyricarb/chlorodincarb、唑酮菌(famoxadone)、咪唑菌酮(fenamidone);
-Qi位点的配合物III抑制剂:氰霜唑(cyazofamid)、amisulbrom、2-甲基丙酸[(3S,6S,7R,8R)-8-苄基-3-[(3-乙酰氧基-4-甲氧基吡啶-2-羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧庚环-7-基]酯、2-甲基丙酸[(3S,6S,7R,8R)-8-苄基-3-[[3-乙酰氧基甲氧基-4-甲氧基吡啶-2-羰基]氨基]-6-甲基-4,9-二氧代-1,5-二氧庚环-7-基]酯、2-甲基丙酸[(3S,6S,7R,8R)-8-苄基-3-[(3-异丁氧基羰氧基-4-甲氧基吡啶-2-羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧庚环-7-基]酯、2-甲基丙酸[(3S,6S,7R,8R)-8-苄基-3-[[3-(1,3-苯并间二氧杂环戊烯-5-基甲氧基)-4-甲氧基吡啶-2-羰基]氨基]-6-甲基-4,9-二氧代-1,5-二氧庚环-7-基]酯、2-甲基丙酸(3S,6S,7R,8R)-3-[[(3-羟基-4-甲氧基-2-吡啶基)羰基]氨基]-6-甲基-4,9-二氧代-8-(苯基甲基)-1,5-二氧庚环-7-基酯;
-配合物II抑制剂(例如羧酰胺类):麦锈灵(benodanil)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、氟吡菌酰胺(fluopyram)、氟酰胺(flutolanil)、氟唑菌酰胺(fluxapyroxad)、呋吡唑灵(furametpyr)、isopyrazam、丙氧灭绣胺(mepronil)、氧化萎锈灵(oxycarboxin)、penflufen、吡噻菌胺(penthiopyrad)、sedaxane、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、N-(4'-三氟甲硫基联苯-2-基)-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺、N-(2-(1,3,3-三甲基丁基)苯基)-1,3-二甲基-5-氟-1H-吡唑-4-甲酰胺、N-[9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-二氟甲基-1-甲基-1H-吡唑-4-甲酰胺;3-二氟甲基-1-甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺,3-三氟甲基-1-甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺,1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺,3-三氟甲基-1,5-二甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺,3-二氟甲基-1,5-二甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺,1,3,5-三甲基-N-(1,1,3-三甲基-2,3-二氢化茚-4-基)吡唑-4-甲酰胺;
-其他呼吸抑制剂(例如配合物I,去偶剂):二氟林(diflumetorim)、(5,8-二氟喹唑啉-4-基)-{2-[2-氟-4-(4-三氟甲基吡啶-2-基氧基)苯基]乙基}胺;硝基苯基衍生物:乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、氟啶胺(fluazinam);嘧菌腙(ferimzone);有机金属化合物:三苯锡基盐,例如薯瘟锡(fentin-acetate)、三苯锡氯(fentin chloride)或毒菌锡(fentin hydroxide);ametoctradin和硅噻菌胺(silthiofam);
B)甾醇生物合成抑制剂(SBI杀真菌剂)
-C14脱甲基酶抑制剂(DMI杀真菌剂):三唑类:戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇M(diniconazole-M)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、oxpoconazole、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、1-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷基甲基]-5-氰硫基-1H-[1,2,4]三唑、2-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷基甲基]-2H-[1,2,4]三唑-3-硫醇;咪唑类:抑霉唑(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizol);嘧啶类、吡啶类和哌嗪类:异嘧菌醇(fenarimol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine);
-δ14-还原酶抑制剂:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸酯(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph)、苯锈啶(fenpropidin)、粉病灵(piperalin)、螺茂胺(spiroxamine);
-3-酮基还原酶抑制剂:环酰菌胺(fenhexamid);
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)、精苯霜灵(benalaxyl-M)、kiralaxyl、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)(mefenoxam)、甲呋酰胺(ofurace)、霜灵(oxadixyl);
-其他:土菌消(hymexazole)、异噻菌酮(octhilinone)、恶喹酸(oxolinic acid)、磺嘧菌灵(bupirimate)、5-氟胞嘧啶、5-氟-2-(对甲苯基甲氧基)嘧啶-4-胺、5-氟-2-(4-氟苯基甲氧基)嘧啶-4-胺;
D)细胞分裂和细胞骨架抑制剂
-微管蛋白抑制剂,如苯并咪唑类、托布津类(thiophanate):苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole)、甲基托布津(thiophanate-methyl);三唑并嘧啶类:5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-a]嘧啶;
-其他细胞分裂抑制剂:乙霉威(diethofencarb)、噻唑菌胺(ethaboxam)、戊菌隆(pencycuron)、氟吡菌胺(fluopicolide)、苯酰菌胺(zoxamide)、苯菌酮(metrafenone)、pyriofenone;
E)氨基酸和蛋白质合成抑制剂
-蛋氨酸合成抑制剂(苯胺基嘧啶类):环丙嘧啶(cyprodinil)、嘧菌胺(mepanipyrim)、二甲嘧菌胺(pyrimethanil);
-蛋白质合成抑制剂:灭瘟素(blasticidin-S)、春雷素(kasugamycin)、水合春雷素(kasugamycin hydrochloride-hydrate)、米多霉素(mildiomycin)、链霉素(streptomycin)、土霉素(oxytetracyclin)、多氧霉素(polyoxine)、井冈霉素(validamycin A);
F)信号转导抑制剂
-MAP/组氨酸蛋白激酶抑制剂:氟菌安(fluoroimid)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin)、拌种咯(fenpiclonil)、氟菌(fludioxonil);
-G蛋白抑制剂:喹氧灵(quinoxyfen);
G)类脂和膜合成抑制剂
-磷脂生物合成抑制剂:克瘟散(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、稻瘟灵(isoprothiolane);
-类脂过氧化:氯硝胺(dicloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl)、联苯、地茂散(chloroneb)、氯唑灵(etridiazole);
-磷脂生物合成和细胞壁沉积:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、双炔酰菌胺(mandipropamid)、丁吡吗啉(pyrimorph)、苯噻菌胺(benthiavalicarb)、异丙菌胺(iprovalicarb)、valifenalate和N-(1-(1-(4-氰基苯基)乙磺酰基)丁-2-基)氨基甲酸4-氟苯基酯;
-影响细胞膜渗透性的化合物和脂肪酸:百维灵(propamocarb)、霜霉威盐酸盐(propamocarb-hydrochlorid);
-脂肪酸酰胺水解酶抑制剂:1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-三氟甲基-1H-吡唑-1-基]乙酮
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)、醋酸铜、氢氧化铜、王铜(copperoxychloride)、碱式硫酸铜、硫;
-硫代-和二硫代氨基甲酸酯类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-有机氯化合物(例如邻苯二甲酰亚胺类、硫酰胺类、氯代腈类):敌菌灵(anilazine)、百菌清(chlorothalonil)、敌菌丹(captafol)、克菌丹(captan)、灭菌丹(folpet)、抑菌灵(dichlofluanid)、双氯酚(dichlorophen)、磺菌胺(flusulfamide)、六氯苯(hexachlorobenzene)、五氯酚(pentachlorphenole)及其盐、四氯苯酞(phthalide)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基苯磺酰胺;
-胍类及其他:胍、多果定(dodine)、多果定游离碱、双胍盐(guazatine)、双胍辛胺(guazatine-acetate)、双胍辛醋酸盐(iminoctadine)、双胍辛胺三乙酸盐(iminoctadine-triacetate)、双八胍盐(iminoctadine-tris(albesilate))、二噻农(dithianon)、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;
I)细胞壁合成抑制剂
-葡聚糖合成抑制剂:井冈霉素(validamycin)、多氧霉素(polyoxin B);黑素合成抑制剂:咯喹酮(pyroquilon)、三环唑(tricyclazole)、氯环丙酰胺(carpropamid)、双氯氰菌胺(dicyclomet)、氰菌胺(fenoxanil);
J)植物防御诱发剂
-噻二唑素(acibenzolar-S-methyl)、噻菌灵(probenazole)、异噻菌胺(isotianil)、噻酰菌胺(tiadinil)、调环酸钙(prohexadione-calcium);膦酸酯类:藻菌磷(fosetyl)、乙磷铝(fosetyl-aluminum)、亚磷酸及其盐;
K)未知作用模式
-拌棉醇(bronopol)、灭螨蜢(chinomethionat)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、咪菌威(debacarb)、哒菌清(diclomezine)、野燕枯(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)、二苯胺、胺苯吡菌酮(fenpyrazamine)、氟联苯菌(flumetover)、磺菌胺、flutianil、磺菌威(methasulfocarb)、氯定(nitrapyrin)、异丙消(nitrothal-isopropyl)、喹啉铜(oxin-copper)、丙氧喹啉(proquinazid)、tebufloquin、叶枯酞、唑菌嗪(triazoxide)、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-(环丙基甲氧亚氨基-(6-二氟甲氧基-2,3-二氟苯基)甲基)-2-苯基乙酰胺、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、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、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、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、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(1,2,3,4-四氢萘-1-基)酰胺、2-{1-[2-(5-甲基-3-三氟甲基吡唑-1-基)乙酰基]哌啶-4-基}噻唑-4-甲酸甲基-(R)-1,2,3,4-四氢萘-1-基酰胺、1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-三氟甲基-1H-吡唑-1-基]乙酮、甲氧基乙酸6-叔丁基-8-氟-2,3-二甲基喹啉-4-基酯、N-甲基-2-{1-[(5-甲基-3-三氟甲基-1H-吡唑-1-基)乙酰基]哌啶-4-基}-N-[(1R)-1,2,3,4-四氢萘-1-基]-4-噻唑甲酰胺、3-[5-(4-甲基苯基)-2,3-二甲基异唑烷-3-基]吡啶、3-[5-(4-氯苯基)-2,3-二甲基异唑烷-3-基]吡啶(啶菌恶唑(pyrisoxazole))、N-(6-甲氧基吡啶-3-基)环丙烷甲酰胺、5-氯-1-(4,6-二甲氧基嘧啶-2-基)-2-甲基-1H-苯并咪唑、2-(4-氯苯基)-N-[4-(3,4-二甲氧基苯基)异唑-5-基]-2-丙-2-炔基氧基乙酰胺;
L)抗真菌的生物控制剂、植物生物活化剂:白粉寄生孢(Ampelomycesquisqualis)(例如来自德国Intrachem Bio GmbH&Co.KG的AQ),黄曲霉(Aspergillusflavus)(例如来自瑞士Syngenta的),出芽短梗霉(Aureobasidiumpullulans)(例如来自德国bio-ferm GmbH的),短小芽孢杆菌(Bacilluspumilus)(例如以和Plus来自AgraQuest Inc.,USA的NRRLAccession No.B-30087),枯草芽孢杆菌(Bacillus subtilis)(例如以 MAX和ASO来自AgraQuest Inc.,USA的分离物NRRLNr.B-21661),解淀粉芽孢杆菌(Bacillus subtilis var.amyloliquefaciens)FZB24(例如来自Novozyme Biologicals,Inc.,USA的),橄榄假丝酵母(Candidaoleophila)I-82(例如来自Ecogen Inc.,USA的),Candida saitoana(例如来自Micro Flo Company,USA(BASF SE)和Arysta的(呈与溶菌酶的混合物)和),脱乙酰壳多糖(例如来自新西兰BotriZen Ltd.的ARMOUR-ZEN),Clonostachys rosea f.catenulata,也称为链孢粘帚菌(Gliocladium catenulatum)(例如分离物J1446:来自芬兰Verdera的),盾壳霉(Coniothyrium minitans)(例如来自德国Prophyta的),寄生隐丛赤壳菌(Cryphonectriaparasitica)(例如来自法国CNICM的栗疫菌(Endothia parasitica)),白色隐球菌(Cryptococcus albidus)(例如来自南非Anchor Bio-Technologies的YIELD),尖镰孢(Fusarium oxysporum)(例如来自意大利S.I.A.P.A.的来自法国Natural Plant Protection的),核果梅奇酵母(Metschnikowiafructicola)(例如来自以色列Agrogreen的),Microdochium dimerum(例如来自法国Agrauxine的),Phlebiopsis gigantea(例如来自芬兰Verdera的),Pseudozyma flocculosa(例如来自加拿大Plant Products Co.Ltd.的),寡雄腐霉(Pythium oligandrum)DV74(例如来自捷克共和国RemesloSSRO,Biopreparaty的),Reynoutria sachlinensis(例如来自Marrone BioInnovations,USA的),黄蓝状菌(Talaromyces flavus)V117b(例如来自德国Prophyta的),棘孢木霉(Trichoderma asperellum)SKT-1(例如来自日本Kumiai Chemical Industry Co.,Ltd.的),深绿木霉(T.atroviride)LC52(例如来自新西兰Agrimm Technologies Ltd的),哈茨木霉(T.harzianum)T-22(例如来自Firma BioWorks Inc.,USA的),哈茨木霉(T.harzianum)TH35(例如来自以色列Mycontrol Ltd.的),哈茨木霉(T.harzianum)T-39(例如来自以色列Mycontrol Ltd.和以色列Makhteshim Ltd.的和TRICHODERMA),哈茨木霉(T.harzianum)和绿色木霉(T.viride)(例如来自新西兰Agrimm Technologies Ltd的TRICHOPEL),哈茨木霉(T.harzianum)ICC012和绿色木霉(T.viride)ICC080(例如来自意大利Isagro Ricerca的WP),多孔木霉(T.polysporum)和哈茨木霉(T.harzianum)(例如来自瑞典BINAB Bio-Innovation AB的),钩木霉(T.stromaticum)(例如来自巴西C.E.P.L.A.C.的),绿木霉(T.virens)GL-21(例如来自Certis LLC,USA的),绿色木霉(T.viride)(例如来自印度Ecosense Labs.(India)Pvt.Ltd.的来自印度T.Stanes&Co.Ltd.的F),绿色木霉(T.viride)TV1(例如来自意大利Agribiotec srl的绿色木霉(T.viride)TV1),奥德曼细基格孢(Ulocladium oudemansii)HRU3(例如来自新西兰Botry-Zen Ltd的);
M)生长调节剂
脱落酸(abscisic acid)、先甲草胺(amidochlor)、嘧啶醇(ancymidol)、6-苄基氨基嘌呤、油菜素内酯(brassinolide)、地乐胺(butralin)、矮壮素阳离子(chlormequat)(氯化矮壮素(chlormequat chloride))、胆碱盐酸盐(choline chloride)、环丙酸酰胺(cyclanilide)、丁酰肼(daminozide)、敌草克(dikegulac)、噻节因(dimethipin)、2,6-二甲基吡啶(2,6-dimethylpuridine)、乙烯利(ethephon)、氟节胺(flumetralin)、调嘧醇(flurprimidol)、达草氟(fluthiacet)、调吡脲(forchlorfenuron)、赤霉酸(gibberellicacid)、抗倒胺(inabenfide)、吲哚-3-乙酸、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、助壮素(mepiquat)(氯化助壮素(mepiquat chloride))、萘乙酸、N-6-苄基腺嘌呤、多效唑、调环酸(prohexadione)(调环酸钙)、茉莉酸诱导体(prohydrojasmon)、赛二唑素(thidiazuron)、抑芽唑(triapenthenol)、三硫代磷酸三丁酯、2,3,5-三碘苯甲酸、抗倒酯(trinexapac-ethyl)和烯效唑;
N)除草剂
-乙酰胺类:乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethenamid)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、异丙甲草胺(metolachlor)、吡草胺(metazachlor)、草萘胺(napropamide)、萘丙胺(naproanilide)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、噻醚草胺(thenylchlor);
-氨基酸衍生物:双丙氨酰膦(bilanafos)、草甘膦(glyphosate)、草铵膦(glufosinate)、草硫膦(sulfosate);
-芳氧基苯氧基丙酸酯类:炔草酯(clodinafop)、氰氟草酯(cyhalofop-butyl)、唑禾草灵(fenoxaprop)、吡氟禾草灵(fluazifop)、吡氟氯禾灵(haloxyfop)、恶唑酰草胺(metamifop)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、精喹禾灵(四氢糠基酯)(quizalofop-p-tefuryl);
-联吡啶类:敌草快阳离子(diquat)、对草快阳离子(paraquat);
-(硫代)氨基甲酸酯类:黄草灵(asulam)、苏达灭(butylate)、长杀草(carbetamide)、异苯敌草(desmedipham)、哌草丹(dimepiperate)、扑草灭(eptam)(EPTC)、禾草畏(esprocarb)、草达灭(molinate)、坪草丹(orbencarb)、苯敌草(phenmedipham)、苄草丹(prosulfocarb)、稗草畏(pyributicarb)、杀草丹(thiobencarb)、野麦畏(triallate);
-环己二酮类:丁氧环酮(butroxydim)、烯草酮(clethodim)、噻草酮(cycloxydim)、环苯草酮(profoxydim)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)、肟草酮(tralkoxydim);
-二硝基苯胺类:氟草胺(benfluralin)、丁氟消草(ethalfluralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)、氟乐灵(trifluralin);
-二苯基醚类:氟锁草醚(acifluorfen)、苯草醚(aclonifen)、治草醚(bifenox)、氯甲草(diclofop)、氯氟草醚(ethoxyfen)、氟黄胺草醚(fomesafen)、乳氟禾草灵(lactofen)、乙氧氟草醚(oxyfluorfen);
-羟基苄腈类:溴苯腈(bromoxynil)、敌草腈(dichlobenil)、碘苯腈(ioxynil);
-咪唑啉酮类:咪草酯(imazamethabenz)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr);
-苯氧基乙酸类:稗草胺(clomeprop)、2,4-二氯苯氧基乙酸(2,4-D)、2,4-DB、2,4-滴丙酸(dichlorprop)、MCPA、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB、2甲4氯丙酸(mecoprop);
-吡嗪类:杀草敏(chloridazon)、氟哒嗪草酯(flufenpyr-ethyl)、达草氟、达草灭(norflurazon)、达草止(pyridate);
-吡啶类:氨草啶(aminopyralid)、二氯皮考啉酸(clopyralid)、吡氟草胺(diflufenican)、氟硫草定(dithiopyr)、氟草同(fluridone)、氟草烟(fluroxypyr)、毒莠定(picloram)、氟吡酰草胺(picolinafen)、噻氟啶草(thiazopyr);
-磺酰脲类:磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、环丙黄隆(cyclosulfamuron)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟啶黄隆(flupyrsulfuron)、酰胺磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、啶咪黄隆(imazosulfuron)、碘磺隆(iodosulfuron)、甲磺胺磺隆(mesosulfuron)、嗪吡嘧磺隆(metazosulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、环丙氧黄隆(oxasulfuron)、氟嘧黄隆(primisulfuron)、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、乙黄黄隆(sulfosulfuron)、噻黄隆(thifensulfuron)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、三氟甲磺隆(tritosulfuron)、1-((2-氯-6-丙基咪唑并[1,2-b]哒嗪-3-基)磺酰基)-3-(4,6-二甲氧基嘧啶-2-基)脲;
-三嗪类:莠灭净(ametryn)、莠去津(atrazine)、草净津(cyanazine)、戊草津(dimethametryn)、乙嗪草酮(ethiozin)、六嗪同(hexazinone)、苯嗪草(metamitron)、赛克津(metribuzin)、扑草净(prometryn)、西玛津(simazine)、特丁津(terbuthylazine)、去草净(terbutryn)、苯氧丙胺津(triaziflam);
-脲类:绿麦隆(chlorotoluron)、香草隆(daimuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、利谷隆(linuron)、噻唑隆(methabenzthiazuron)、丁唑隆(tebuthiuron);
-其他乙酰乳酸合成酶抑制剂:双草醚钠盐(bispyribac-sodium)、氯酯磺草胺(cloransulam-methyl)、唑嘧磺胺(diclosulam)、双氟磺草胺(florasulam)、氟酮磺隆(flucarbazone)、氟唑啶草(flumetsulam)、唑草磺胺(metosulam)、嘧苯胺磺隆(ortho-sulfamuron)、五氟磺草胺(penoxsulam)、丙氧基卡巴腙(propoxycarbazone)、丙酯草醚(pyribambenz-propyl)、嘧苯草肟(pyribenzoxim)、环酯草醚(pyriftalid)、肟啶草(pyriminobac-methyl)、pyrimisulfan、嘧硫苯甲酸(pyrithiobac)、pyroxasulfon、甲氧磺草胺(pyroxsulam);
-其他:胺唑草酮(amicarbazone)、三唑胺(aminotriazole)、莎稗磷(anilofos)、beflubutamid、草除灵(benazolin)、bencarbazone、benfluresate、吡草酮(benzofenap)、噻草平(bentazone)、苯并双环酮(benzobicyclon)、bicyclopyrone、除草定(bromacil)、溴丁酰草胺(bromobutide)、氟丙嘧草酯(butafenacil)、草胺磷(butamifos)、胺草唑(cafenstrole)、氟酮唑草(carfentrazone)、吲哚酮草酯(cinidon-ethyl)、敌草索(chlorthal)、环庚草醚(cinmethylin)、异恶草酮(clomazone)、苄草隆(cumyluron)、cyprosulfamide、麦草畏(dicamba)、野燕枯、二氟吡隆(diflufenzopyr)、稗内脐蠕孢菌(Drechslera monoceras)、敌草腈(endothal)、乙呋草黄(ethofumesate)、乙苯酰草(etobenzanid)、fenoxasulfone、四唑酰草胺(fentrazamide)、氟烯草酸(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、胺草唑(flupoxam)、氟咯草酮(fluorochloridone)、呋草酮(flurtamone)、茚草酮(indanofan)、异恶草胺(isoxaben)、异氟草(isoxaflutole)、环草定(lenacil)、敌稗(propanil)、拿草特(propyzamide)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、硝草酮(mesotrione)、甲胂酸(methylarsonic acid)、抑草生(naptalam)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazon)、氯嗪草(oxaziclomefone)、戊唑草(pentoxazone)、唑啉草酯(pinoxaden)、双唑草腈(pyraclonil)、吡草醚(pyraflufen-ethyl)、pyrasulfotole、苄草唑(pyrazoxyfen)、吡唑特(pyrazolynate)、灭藻醌(quinoclamine)、嘧啶肟草醚(saflufenacil)、磺草酮(sulcotrione)、磺胺草唑(sulfentrazone)、特草定(terbacil)、tefuryltrione、tembotrione、thiencarbazone、topramezone、(3-[2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢-2H-嘧啶-1-基)苯氧基]吡啶-2-基氧基)乙酸乙酯、6-氨基-5-氯-2-环丙基嘧啶-4-甲酸甲酯、6-氯-3-(2-环丙基-6-甲基苯氧基)哒嗪-4-醇、4-氨基-3-氯-6-(4-氯苯基)-5-氟吡啶-2-甲酸、4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)吡啶-2-甲酸甲酯和4-氨基-3-氯-6-(4-氯-3-二甲基氨基-2-氟苯基)吡啶-2-甲酸甲酯。
O)杀虫剂:
-有机(硫代)磷酸酯:高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、毒虫畏(chlorfenvinphos)、二嗪农(diazinon)、敌敌畏(dichlorvos)、百治磷(dicrotophos)、乐果(dimethoate)、乙拌磷(disulfoton)、乙硫磷(ethion)、杀螟松(fenitrothion)、倍硫磷(fenthion)、异唑磷(isoxathion)、马拉硫磷(malathion)、甲胺磷(methamidophos)、杀扑磷(methidathion)、甲基对硫磷(methyl-parathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、砜吸磷(oxydemeton-methyl)、对氧磷(paraoxon)、一六零五(parathion)、稻丰散(phenthoate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、甲拌磷(phorate)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、丙硫磷(prothiofos)、田乐磷(sulprophos)、杀虫威(tetrachlorvinphos)、特丁磷(terbufos)、三唑磷(triazophos)、敌百虫(trichlorfon);
-氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、双氧威(fenoxycarb)、呋线威(furathiocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、唑蚜威(triazamate);
-合成除虫菊酯类:丙烯除虫菊(allethrin)、氟氯菊酯(bifenthrin)、氟氯氰菊酯(cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、苯醚氰菊酯(cyphenothrin)、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、溴氰菊酯(deltamethrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、咪炔菊酯(imiprothrin)、氯氟氰菊酯(lambda-cyhalothrin)、氯菊酯(permethrin)、炔酮菊酯(prallethrin)、除虫菊酯(pyrethrin)I和II、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、丙氟菊酯(profluthrin)、四氟甲醚菊酯(dimefluthrin);
-昆虫生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类:定虫隆(chlorfluazuron)、灭蝇胺(cyramazin)、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)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);噻嗪酮(buprofezin)、茂醚(diofenolan)、噻螨酮(hexythiazox)、特苯唑(etoxazole)、四螨嗪(clofentazine);b)蜕皮激素拮抗剂:特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、艾扎丁(azadirachtin);c)保幼激素类似物:蚊蝇醚(pyriproxyfen)、蒙五一五(methoprene)、双氧威;d)类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat);
-烟碱受体激动剂/拮抗剂化合物:噻虫胺(clothianidin)、呋虫胺(dinotefuran)、flupyradifurone、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、吡虫清(acetamiprid)、噻虫啉(thiacloprid)、1-(2-氯噻唑-5-基甲基)-2-硝酰亚氨基(nitrimino)-3,5-二甲基-[1,3,5]三嗪烷(triazinane);
-GABA拮抗剂化合物:硫丹(endosulfan)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)、pyrafluprole、pyriprole、5-氨基-1-(2,6-二氯-4-甲基苯基)-4-亚磺酰氨酰基(sulfinamoyl)-1H-吡唑-3-硫代甲酰胺;
-大环内酯杀虫剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin)、米尔螨素(milbemectin)、lepimectin、艾克敌105(spinosad)、乙基多杀菌素(spinetoram);
-线粒体电子传输抑制剂(METI)I杀螨剂:喹螨醚(fenazaquin)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、嘧虫胺(flufenerim);
-METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
-去偶剂:氟唑虫清(chlorfenapyr);
-氧化磷酸化抑制剂:三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite);
-蜕皮干扰剂化合物:灭蝇胺(cryomazine);
-混合功能氧化酶抑制剂:增效醚(piperonyl butoxide);
-钠通道阻断剂:二唑虫(indoxacarb)、氰氟虫胺(metaflumizone);
-其他:benclothiaz、联苯肼酯(bifenazate)、杀螟丹(cartap)、氟啶虫酰胺(flonicamid)、啶虫丙醚(pyridalyl)、拒嗪酮(pymetrozine)、硫、硫环杀(thiocyclam)、氟虫酰胺(flubendiamide)、氯虫酰胺(chlorantraniliprole)、cyazypyr(HGW86)、cyenopyrafen、吡氟硫磷(flupyrazofos)、丁氟螨酯(cyflumetofen)、amidoflumet、imicyafos、双三氟虫脲(bistrifluron)和pyrifluquinazon。
此外,本发明涉及包含至少一种化合物I或VIII(组分1)和至少一种例如选自上述A)-O)组,尤其是一种其他杀真菌剂,例如一种或多种选自A)-L)组的杀真菌剂的可用于植物保护的其他活性物质(组分2)以及需要的话一种合适的溶剂或固体载体的混合物的农化组合物。这些混合物特别令人感兴趣,因为它们中的许多在相同施用率下对有害真菌显示出更高效力。此外,用化合物I或VIII和至少一种选自上述A)-L)组的杀真菌剂的混合物防治有害真菌比用单独的化合物I或VIII或选自A)-L)组的单独杀真菌剂防治那些真菌更有效。通过将化合物I或VIII与至少一种选自A)-O)组的活性物质一起施用,可以得到协同增效效果,即得到的效果大于单独效果的简单加和(协同增效混合物)。
这可以通过同时,即联合(例如作为桶混物)或分开,或依次施用化合物I或VIII和至少一种其他活性物质而得到,其中选择各次施用之间的时间间隔以确保最初施用的活性物质在施用其他活性物质时仍以足够量存在于作用位置。施用顺序对本发明的实施并不重要。
在二元混合物即包含一种化合物I或VIII(组分1)和一种其他活性物质(组分2),例如一种选自A)-O)组的活性物质的本发明组合物中,组分1和组分2的重量比通常取决于所用活性物质的性能,它通常为1:100-100:1,常常为1:50-50:1,优选为1:20-20:1,更优选为1:10-10:1,尤其为1:3-3:1。
在三元混合物即包含一种化合物I或VIII(组分1)以及第一种其他活性物质(组分2)和第二种其他活性物质(组分3),例如两种选自A)-O)组的活性物质的本发明组合物中,组分1和组分2的重量比通常取决于所用活性物质的性能,它优选为1:50-50:1,尤其为1:10-10:1,并且组分1和组分3的重量比优选为1:50-50:1,尤其为1:10-10:1。
还优选包含化合物I或VIII(组分1)和至少一种选自A)组,特别是选自腈嘧菌酯、醚菌胺、氟嘧菌酯、亚胺菌、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、唑酮菌、咪唑菌酮、bixafen、啶酰菌胺、氟吡菌酰胺、氟唑菌酰胺、isopyrazam、penflufen、吡噻菌胺、sedaxane、ametoctradin、氰霜唑、氟啶胺、三苯锡基盐如薯瘟锡的活性物质(组分2)的混合物。
优选包含式I或VIII化合物(组分1)和至少一种选自B)组,特别是选自环唑醇、醚唑、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、环戊唑菌、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、三唑酮、唑菌醇、戊唑醇、氟醚唑、戊叉唑菌、丙氯灵、异嘧菌醇、嗪氨灵、吗菌灵、丁苯吗啉、克啉菌、苯锈啶、螺茂胺、环酰菌胺的活性物质(组分2)的混合物。
优选包含式I或VIII化合物(组分1)和至少一种选自C)组,特别是选自甲霜灵,精甲霜灵(mefenoxam)、甲呋酰胺的活性物质(组分2)的混合物。
优选包含式I或VIII化合物(组分1)和至少一种选自D)组,特别是选自苯菌灵、多菌灵、甲基托布津、噻唑菌胺、氟吡菌胺、苯酰菌胺、苯菌酮、pyriofenone的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自E)组,特别是选自环丙嘧啶、嘧菌胺、二甲嘧菌胺的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自F)组,特别是选自异丙定、氟菌、烯菌酮、喹氧灵的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自G)组,特别是选自烯酰吗啉、氟吗啉、异丙菌胺、苯噻菌胺、双炔酰菌胺、百维灵的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自H)组,特别是选自醋酸铜、氢氧化铜、王铜、硫酸铜、硫、代森锰锌、代森联、甲基代森锌、福美双、敌菌丹、灭菌丹、百菌清、抑菌灵、二噻农的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自I)组,特别是选自氯环丙酰胺和氰菌胺的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自J)组,特别是选自噻二唑素、噻菌灵、噻酰菌胺、藻菌磷、乙磷铝、H3PO3及其盐的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自K)组,特别是选自清菌脲、丙氧喹啉和N-甲基-2-{1-[(5-甲基-3-三氟甲基-1H-吡唑-1-基)乙酰基]哌啶-4-基}-N-[(1R)-1,2,3,4-四氢萘-1-基]-4-噻唑甲酰胺的活性物质(组分2)的混合物。
还优选包含化合物I或VIII(组分1)和至少一种选自L)组,特别是选自枯草芽孢杆菌菌株NRRL No.B-21661、短小芽孢杆菌菌株NRRL No.B-30087和奥德曼细基格孢的活性物质(组分2)的混合物。
因此,本发明此外还涉及包含一种化合物I或VIII(组分1)和一种其他活性物质(组分2)的组合物,该其他活性物质选自表B的B-1至B-372行的“组分2”栏。
另一实施方案涉及表B中所列组合物B-1至B-372,其中表B的一行在每种情况下对应于包含本说明书中列举的式I化合物之一(组分1)和所述行中所述选自A)-O)组的相应其他活性物质(组分2)的杀真菌组合物。优选所述组合物以协同增效有效量包含活性物质。
表B:包含一种列举的化合物I和一种选自A)-O)组的其他活性物质的组合物
另一实施方案涉及表B2中所列组合物B2-1至B2-372,其中表B的一行在每种情况下对应于包含本说明书中列举的式VIII化合物之一(组分1)和所述行中所述的选自A)-O)组的其他活性物质(组分2)的杀真菌组合物。优选所述组合物以协同增效有效量包含活性物质。
表B2:包含一种列举化合物VIII和一种选自A)-O)组的其他活性物质的组合物。该表对应于表B,其中在第一栏中列举混合物的编号/名称命名为“B2-…”而不是“B-…”且在第二栏中每行描述“一种列举化合物VIII”而不是“一种列举化合物I”。
称为组分2的活性物质、其制备及其对有害真菌的活性是已知的(参见http://www.alanwood.net/pesticides/);这些物质可市购。由IUPAC命名法描述的化合物、其制备及其杀真菌活性也是已知的(参见Can.J.Plant Sci.48(6),587-94,1968;EP-A141317;EP-A152031;EP-A226917;EP-A243970;EP-A256503;EP-A428941;EP-A532022;EP-A1028125;EP-A1035122;EP-A1201648;EP-A1122244,JP2002316902;DE19650197;DE10021412;DE102005009458;US3,296,272;US3,325,503;WO98/46608;WO99/14187;WO99/24413;WO99/27783;WO00/29404;WO00/46148;WO00/65913;WO01/54501;WO01/56358;WO02/22583;WO02/40431;WO03/10149;WO03/11853;WO03/14103;WO03/16286;WO03/53145;WO03/61388;WO03/66609;WO03/74491;WO04/49804;WO04/83193;WO05/120234;WO05/123689;WO05/123690;WO05/63721;WO05/87772;WO05/87773;WO06/15866;WO06/87325;WO06/87343;WO07/82098;WO07/90624,WO11/028657)。
活性物质的混合物可以通过常规方法,例如通过对化合物I的组合物所给方法制备成除了活性成分外还包含至少一种惰性成分的组合物。
关于该类组合物的常规成分,参考对含有化合物I的组合物所给解释。
本发明活性物质的混合物适合作为杀真菌剂,正如式I化合物那样。它们的特征在于对宽范围的植物病原性真菌,尤其是选自子囊菌纲、担子菌纲、半知菌纲和Peronosporomycetes(同义词卵菌纲)的真菌具有显著的效力。此外,分别参考有关化合物以及含有化合物I的组合物的杀真菌活性的解释。
I.合成实施例
适当改变起始化合物,使用下列合成实施例中所示程序得到其他化合物I。所得化合物与物理数据一起列于下表I中。
实施例1:制备1-[2-[2-氯-4-(4-氯苯氧基)苯基]-2-环丙基-2-甲氧基乙基]-1,2,4-三唑(化合物I-1)
步骤1:
在室温下向1-溴-2-氯-4-(4-氯苯氧基)苯(100.0g,310mmol)在250mL THF中的溶液中滴加异丙基氯化镁/氯化锂配合物(246mL,1.3M,在THF中)并搅拌1小时。然后在轻度冷却(10-20℃)下将反应混合物滴加到环丙酰氯(40.2g,380mmol)、三氯化铝(1.13g,10mmol)、氯化锂(724mg)和氯化铜(845mg,10mmol)在750mL THF中的溶液中。在室温下15分钟后在10℃下将所得混合物用氯化铵水溶液猝灭并用MTBE萃取。有机相依次用氨水溶液、氯化铵水溶液和HCl水溶液洗涤至达到中性pH。在干燥和蒸发之后得到产物[2-氯-4-(4-氯苯氧基)苯基]环丙基甲酮(94.0g),将其不经提纯而用于下一步中。1H-NMR(CDCl3;400MHz):δ(ppm)=1.10(m,2H);1.30(m,2H);2.50(m,1H);6.80-7.00(m,4H);7.30(d,2H);7.55(d,1H)。
步骤2:
在氩气和5℃下向氢化钠(11.04g,460mmol)在THF(800mL)和无水DMSO(300mL)中的溶液中滴加三甲基碘化锍(89.79g,440mmol)在无水DMSO(1L)中的溶液。将该混合物在5℃下搅拌1小时,然后滴加在DMSO(500mL)中的12-氯-4-(4-氯苯氧基)苯基]环丙基甲酮(72.28g,200mmol)。然后将所得混合物温热过夜至室温并用氯化铵水溶液和冰水猝灭,然后用MTBE萃取。将有机溶剂用水洗涤,干燥并蒸发,以黄色油状物得到2-[2-氯-4-(4-氯苯氧基)苯基]-2-环丙基环氧乙烷(75.5g,纯度85%)。1H-NMR(CDCl3;400MHz):δ(ppm)=0.30-0.50(m,4H);1.25(m,1H);2.80(d,1H);3.0(d,1H);6.85(d,1H);6.90-7.00(m,3H);7.25-7.40(m,3H)。
步骤3:
在室温下向溶于N-甲基-2-吡咯烷酮(850mL)中的2-[2-氯-4-(4-氯苯氧基)苯基]-2-环丙基环氧乙烷(75.5g,188mmol)中加入氢氧化钠(18.8g,470mmol)和三唑(64.94g,940mmol)。然后将该混合物在125℃下搅拌4小时。然后加入氯化铵溶液,将该混合物用MTBE萃取并用水洗涤,然后用氯化钠水溶液洗涤。粗残余物通过在硅胶上的快速层析提纯。然后在二异丙醚/庚烷(1:1)中重结晶所得固体,以白色固体得到1-[2-氯-4-(4-氯苯氧基)苯基]-1-环丙基-2-(1,2,4-三唑-1-基)乙醇(56.0g,76%,m.p.=170℃)。1H-NMR(CDCl3;400MHz):δ(ppm)=0.25(m,1H);0.38-0.50(m,2H);0.60(m,1H);1.80(m,1H);4.5(宽s,1H);4.58(d,1H);5.35(d,1H);6.75(d,1H);6.90(m,3H);7.30(d,2H);7.60(d,1H);7.85(s,1H);8.00(s,1H)。
步骤4:
在室温下向1-[2-氯-4-(4-氯苯氧基)苯基]-1-环丙基-2-(1,2,4-三唑-1-基)乙醇(0.5g)在15mL THF中的溶液中加入氢化钠(40.0g)中。然后将反应混合物搅拌30分钟,然后加入碘甲烷(0.23g)并在室温下搅拌18小时,然后在70℃下搅拌6小时并在120℃下搅拌10小时。在加入氯化钠水溶液之后,将该混合物用二氯甲烷萃取,干燥,蒸发。粗残余物通过在硅胶上的快速层析提纯,以无色油状物得到1-[2-[2-氯-4-(4-氯苯氧基)苯基]-2-环丙基-2-甲氧基乙基]-1,2,4-三唑(489mg;HPLC-MS Rt=1.30min;质量=404)。1H-NMR(CDCl3;400MHz):δ(ppm)=0.45(m,1H);0.80(m,2H);1.25(m,1H);1.85(m,1H);3.40(s,3H);4.45(d,1H);4.82(d,1H);6.75(d,1H);6.90(d,2H);7.05(s,1H);7.30-7.40(m,3H);7.75(s,1H);7.90(s,1H)。
实施例2:制备1-[(E)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-苯基-2-丙-2-炔氧基丁-3-烯基]-1,2,4-三唑(化合物I-7)
该醇(E)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-苯基-1-(1,2,4-三唑-1-基)丁-3-烯-2-醇可以如下列参考文献所述制备:Journal of Agricultural and Food Chemistry(2009),57(11),4854-4860。
在室温下向(E)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-phenyl-1-(1,2,4-三唑-1-基)丁-3-烯-2-醇(620mg,1.3mmol)在8mL THF中的溶液中加入氢化钠(40.0g)。然后将反应混合物搅拌30分钟,然后加入炔丙基溴(0.20g,1.62mmol)并在80℃下搅拌5小时。在加入氯化钠水溶液之后,将该混合物用二氯甲烷萃取,干燥,蒸发。粗残余物通过在硅胶上的快速层析提纯,以黄色油状物得到1-[(E)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-苯基-2-丙-2-炔氧基丁-3-烯基]-1,2,4-三唑(490mg;HPLC-MS Rt=1.41min;质量=490)。
以类似方式制备表I中所列化合物I。
表I:
实施例号 | X1 | X2 | R1 | R2 | HPLC*Rt(min) |
I-1 | Cl | Cl | C3H5 | CH3 | 1.30 |
I-2 | Cl | Cl | C3H5 | CH2CH=CH2 | 1.37 |
I-3 | Cl | Cl | C3H5 | C2H5 | 1.35 |
I-4 | Cl | Cl | C3H5 | CH2C≡CH | 1.29 |
I-5 | Cl | Cl | C3H5 | CH2C6H5 | 1.43 |
I-6 | Cl | Cl | C3H5 | CH2C3H5 | 1.41 |
I-7 | Cl | Cl | (E)-CH=CHC6H5 | CH2C≡CH | 1.41 |
*:HPLC方法数据:
移动相:A:水+0.1%TFA,B:乙腈;梯度:在1.5分钟内5%B至100%B;温度:60℃;MS方法:ESI正型;质量区域(m/z):10-700;流速:在1.5分钟内0.8ml/min至1.0ml/min;柱:Kinetex XB C181.7μ50×2.1mm;设备:Shimadzu Nexera LC-30LCMS-2020
II.对有害真菌的作用实施例
式I化合物的杀真菌作用由下列试验证实:
微试验
在二甲亚砜中将活性化合物分开配制成浓度为10000ppm的储备溶液。M1在小麦上对由小麦壳针孢引起的叶斑病的活性(Septtr)
将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入小麦壳针孢在生物麦芽或酵母-细菌蛋白胨-甘油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。化合物I-1和I-2在32ppm下显示出2%或更小的生长。
M2在微滴定板中对稻瘟病—稻瘟病菌的活性(Pyrior)
将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入稻瘟病菌在生物麦芽或酵母-细菌蛋白胨-甘油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。
M3在微滴定试验中在大麦上对由网斑病—大麦网斑内脐蠕孢的活性(Pyrnte)
将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入大麦网斑内脐蠕孢在生物麦芽或酵母-细菌蛋白胨-甘油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。
将测量的参数与不含活性化合物的对照方案的生长(100%)以及不含真菌和活性化合物的空白值相比较,以确定病原体在各活性化合物中的相对生长百分数。
A)温室
以几个步骤制备喷雾溶液:
制备储备溶液:将溶剂/乳化剂比例(体积)为99/1的丙酮和/或二甲亚砜与基于乙氧基化烷基酚的润湿剂/乳化剂Wettol的混合物加入25mg化合物中,使总量为5ml。然后加入水至总体积为100ml。用所述溶剂-乳化剂-水混合物稀释该储备溶液至给定浓度。
G1对小麦上由小麦壳针孢引起的叶斑病的治疗性防治(Septtr K7)
将盆栽小麦秧苗的叶子用小麦壳针孢的含水孢子悬浮液接种。然后将试验植株立即转移到18-22℃和相对湿度接近100%的潮湿室中。4天后将植株转移到18-22℃和相对湿度接近70%的室中。接种7天后将植株用如所述制备的活性化合物或其混合物的含水悬浮液喷雾至滴流。然后将植株转移回到18-22℃和相对湿度接近70%的室中。4周后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。
B)温室
以几个步骤制备喷雾溶液:
制备储备溶液:将溶剂/乳化剂比例(体积)为99/1的丙酮和/或二甲亚砜与基于乙氧基化烷基酚的润湿剂/乳化剂Wettol的混合物加入25mg化合物中,使总量为5ml。然后加入水至总体积为100ml。用所述溶剂-乳化剂-水混合物稀释该储备溶液至给定浓度。
G1对小麦上由小麦壳针孢引起的叶斑病的预防性防治(Septtr P7)
将盆栽小麦秧苗的叶子用如下所述制备的活性成分或其混合物的含水悬浮液喷雾至滴流。将植株风干。7天后将植株用小麦壳针孢的含水孢子悬浮液接种。然后将试验植株立即转移到18-22℃和相对湿度接近100%的潮湿室中。4天后将植株转移到18-22℃和相对湿度接近70%的室中。4周后以患病叶面积%肉眼评价叶子上的真菌侵袭程度。在该试验中,分别用250ppm来自实施例I-1、I-2、I-3、I-4、I-5和I-6的活性物质处理的植株显示出小于或等于1%的侵染,而未处理植株70%被侵染。
G2对西红柿上的早疫病(早疫链格孢)的预防性杀真菌防治(Alteso P1)
使西红柿植株的幼苗在盆中生长。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含水悬浮液喷雾至滴流。第二天将被处理植株用早疫链格孢的含水悬浮液接种。然后将试验植株立即转移至潮湿室中。在18-20℃和接近100%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300ppm来自实施例I-1、I-2、I-3、I-4和I-6的活性物质处理的植株显示出小于或等于10%的侵染,而未处理植株90%被侵染。
G3对小麦上由小麦叶锈菌引起的褐锈病的预防性防治(Puccrt P7)
将盆栽小麦秧苗的最早发育的两片叶子用含有如下所述浓度的活性成分或其混合物的含水悬浮液喷雾至滴流。7天后将植株用小麦叶锈菌的孢子接种。为了确保人工接种的成功,将植株转移到相对湿度95-99%和20-24℃的无光潮湿室中24小时。然后将试验植株在20-24℃和65-70%相对湿度下在温室中栽培6天。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来自实施例I-1、I-2、I-3、I-4、I-5和I-6的活性物质处理的植株显示出小于或等于3%的侵染,而未处理植株90%被侵染。
G4对大豆上由豆薯层锈菌引起的大豆锈病的治疗性防治(Phakpa K4)
将盆栽大豆秧苗的叶子用豆薯层锈菌的孢子接种。为了确保人工接种的成功,将植株转移到相对湿度约95%和20-24℃的潮湿室中24小时。第二天将植株在23-27℃和60-80%相对湿度下在温室中栽培3天。然后将植株用含有如下所述浓度的活性成分或其混合物的含水悬浮液喷雾至滴流。将植株风干。然后将试验植株在23-27℃和60-80%相对湿度下在温室中栽培14天。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来自实施例I-1、I-2、I-3、I-4和I-5的活性物质处理的植株显示出小于或等于10%的侵染,而未处理植株70%被侵染。
微试验
在二甲亚砜中将活性化合物分开配制成浓度为10000ppm的储备溶液。M1在微滴定板试验中对灰霉病—灰葡萄孢的活性(Botrci)
将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。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。化合物I-1、I-3、I-4和I-5在32ppm下显示出10%或更小的生长。
M2对由颖枯球腔菌引起的小麦叶斑病的活性(Leptno)
将储备溶液根据比例混合,用移液管移到微滴定板(MTP)中并用水稀释至所述浓度。然后加入颖枯球腔菌在生物麦芽或酵母-细菌蛋白胨-甘油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。化合物I-1、I-2、I-3、I-4、I-5和I-6在32ppm下显示出7%或更小的生长。
将测量的参数与不含活性化合物的对照方案的生长(100%)以及不含真菌和活性化合物的空白值相比较,以确定病原体在各活性化合物中的相对生长百分数。将这些百分数转化成效力。
Claims (13)
1.式I化合物或其可农用盐
其中
X1、X2相互独立地选自卤素;
R1为C3-C8环烷基或C3-C8环烷基-C1-C4烷基;
R2为C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C8环烷基-C1-C4烷基或苯基-C1-C4烷基。
2.根据权利要求1的化合物,其中X1为Cl。
3.根据权利要求1的化合物,其中X2为Cl。
4.根据权利要求2的化合物,其中X2为Cl。
5.根据权利要求1的化合物,其中X1和X2为Cl,R1为未取代的环丙基且R2为CH3、C2H5、CH2CH=CH2、CH2C≡CH、CH2C6H5或CH2C3H5。
6.一种制备如权利要求1-5中任一项所定义的式I化合物的方法,包括使式IIIa化合物:
其中X2如权利要求1或3所定义,Y为F或Cl且X3为I或Br,
与式II的卤代苯酚在碱性条件下反应:
其中X1如权利要求1或2所定义,
以及使所得式IVa化合物与异丙基溴化镁反应,然后与乙酰氯反应:
其中X1和X2如权利要求1-3中任一项所定义,
以及将所得式V化合物卤化:
其中X1和X2如权利要求1-3中任一项所定义,
以及使所得式VI化合物在碱性条件下与1H-1,2,4-三唑反应:
其中X1和X2如权利要求1-3中任一项所定义且Hal表示卤素;
以及使所得式VII化合物:
其中X1和X2如权利要求1-3中任一项所定义,
与R1-M反应,其中R1如权利要求1或5所定义且M为MgBr、MgCl、Li或Na,
以及使所得式VIII化合物:
其中X1、X2和R1如权利要求1-5中任一项所定义,
在碱性条件下与R2-LG反应,其中R2如权利要求1所定义且LG为可亲核置换的离去基团,
得到式I化合物。
7.一种制备如权利要求1-5中任一项所定义的式I化合物的方法,包括使式IIIa化合物:
其中X2如权利要求1或3所定义,Y为F或Cl且X3为I或Br,
与异丙基卤化镁反应,然后与式IX化合物R1-COCl反应,其中R1如权利要求1或5所定义;
以及将所得式X化合物:
其中X2如权利要求1或3所定义,Y为F或Cl且R1如权利要求1或5所定义,
在碱性条件下用式II的卤代苯酚转化:
其中X1如权利要求1或2所定义;
以及使所得式Va化合物与三甲基(氧化)锍卤化物反应:
其中X1、X2和R1如权利要求1-5中任一项所定义,
以及使所得式XI化合物在碱性条件下与1H-1,2,4-三唑反应:
其中X1、X2和R1如权利要求1-5中任一项所定义,
以及使所得式VIII化合物:
其中X1、X2和R1如权利要求1-5中任一项所定义,
在碱性条件下与R2-LG反应,其中R2如权利要求1所定义且LG为可亲核置换的离去基团,
得到式I化合物。
8.一种制备如权利要求1-5中任一项所定义的式I化合物的方法,包括使式XI化合物:
其中X1、X2和R1如权利要求1-5中任一项所定义,
在酸性条件下与R2-OH反应,其中R2如权利要求1所定义;
以及使所得式XII化合物与卤化剂或磺化剂反应:
其中X1、X2、R1和R2如权利要求1-5中任一项所定义,
以及使所得式XIII化合物与1H-1,2,4-三唑反应:
其中X1、X2、R1和R2如权利要求1-5中任一项所定义且LG为相应的可亲核置换的离去基团;
得到化合物I。
9.式VIII化合物:
其中X1、X2和R1如权利要求1-5中任一项所定义,如下化合物除外:1)其中X1和X2为Cl且R1为环丙基、C4H7、环己基、CH2-C3H5、环戊基、CH(CH3)C3H5或1-甲基环丙基的化合物。
10.农化组合物,其中所述组合物包含助剂和至少一种如权利要求1-5或9中任一项所定义的式I或VIII化合物或其可农用盐。
11.根据权利要求10的组合物,额外包含其他活性物质。
12.如权利要求1-5或9中任一项所定义的式I或VIII化合物、其可农用盐或如权利要求10或11所定义的组合物在防治植物病原性真菌中的用途。
13.一种处理种子的方法,其中以0.1g-10kg/100kg种子的量将至少一种如权利要求1-5或9中任一项所定义的式I或VIII化合物或如权利要求10或11所定义的组合物施用于种子。
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Also Published As
Publication number | Publication date |
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CR20130678A (es) | 2014-03-13 |
BR112014002499A2 (pt) | 2017-02-21 |
ZA201401797B (en) | 2016-01-27 |
KR20140054235A (ko) | 2014-05-08 |
CA2838332A1 (en) | 2013-02-21 |
IL229954A0 (en) | 2014-03-06 |
JP2014525406A (ja) | 2014-09-29 |
AR087537A1 (es) | 2014-04-03 |
MX2013014348A (es) | 2014-04-30 |
PE20141412A1 (es) | 2014-10-23 |
WO2013024080A1 (en) | 2013-02-21 |
EP2744795B1 (en) | 2015-12-30 |
CO6900161A2 (es) | 2014-03-20 |
UY34261A (es) | 2013-02-28 |
AU2012296890A1 (en) | 2014-02-20 |
EP2744795A1 (en) | 2014-06-25 |
CL2013003672A1 (es) | 2014-07-11 |
US20140187422A1 (en) | 2014-07-03 |
CN103717579A (zh) | 2014-04-09 |
EA201400232A1 (ru) | 2014-07-30 |
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