CN1261426C - 具有杀真菌活性的碘代苯并吡喃－4－酮衍生物 - Google Patents

具有杀真菌活性的碘代苯并吡喃－4－酮衍生物 Download PDF

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CN1261426C
CN1261426C CNB028151372A CN02815137A CN1261426C CN 1261426 C CN1261426 C CN 1261426C CN B028151372 A CNB028151372 A CN B028151372A CN 02815137 A CN02815137 A CN 02815137A CN 1261426 C CN1261426 C CN 1261426C
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CN1537108A (zh
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T·维格曼
N·休瑟
R·K·普鲁斯
J·佩莱斯
S·卡波尼
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Abstract

本发明涉及具有抗植物病原性生物体的杀真菌性质的碘代苯并吡喃-4-酮衍生物，制备这些衍生物的方法，其植保应用，以及包含这些衍生物与一种或多种其它杀真菌化合物联用的杀真菌组合物。

Description

具有杀真菌活性的碘代苯并吡喃-4-酮衍生物
叙述
本发明涉及具有抗植物病原性生物体的杀真菌性质的碘代苯并吡喃-4-酮衍生物，制备这些衍生物的方法，其植保应用，以及含有这些衍生物与一种或多种其它杀真菌化合物联用的杀真菌组合物。
国际专利申请WO-97/13762具体叙述了卤代苯并吡喃酮类型的衍生物。该文件用极通用的化学公式公开了极大量化合物。然而，作为实例给出的化合物基本上是在苯环上带有溴原子或碳链的化合物。因此，该文件所集中表现的化合物没有用碘原子取代，这和本发明的情况不一样。事实上，该文件只公开了2个碘化的化合物，而且没有表明这些化合物所具有的性质优于其它化合物特别是溴化的衍生物。
现在已经发现，某些特殊的碘代苯并吡喃-4-酮衍生物具有优异的抗植物病原性生物体的杀真菌性质。当这些化合物与一种或多种其它杀真菌化合物作为混合物使用时，这些性质还可得到进一步改善。
本发明的第一方面涉及式(I)化合物
Figure C0281513700041
其中：
碘原子取代在5、6、7或8位上；
R1选自卤原子、取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、和取代的或未取代的C1-C6炔基；
R2选自取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、和取代的或未取代的C1-C6炔基、3-7元碳环或杂环(它们是取代的或未取代的，饱和的，不饱和的或芳族的)、卤原子、氰基、-W-R3基团；
W选自氧、硫或基团-NR4；
R3和R4可以相同或不同，各自独立选自氢原子、取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、和取代的或未取代的C1-C6炔基、烷氧基、氨基、3-7元碳环或杂环(它们是取代的或未取代的，饱和的，不饱和的或芳族的)，R3和R1可以一起形成5-7元杂环，它们可以是饱和的，不饱和的或芳族的，且还可以包含另一个杂原子；它们可能的几何和/或光学异构体(纯的形式或按任何比例的混合物形式，包括外消旋混合物)，它们可能的N-氧化物，与酸的加成盐，和它们可能的金属或准金属配合物；当碘是在6位，当R1是正丙基并当W代表氧时，R3与甲基或丁基不同。
当式(I)化合物的这些基团被取代时，它们以优选的方式被各自独立选自以下的一个或多个基团取代：烷基、链烯基或炔基；卤原子；氰基；三烷基甲硅烷基；烷氧基；烷硫基；羟基；硝基；氨基；酰基；酰氧基；苯基；杂环基；苯硫基；苯氧基；杂环氧基；或杂环硫基和氧化的衍生物，并可能任选地被含有硫代基团的化学部分取代。
术语“杂环基”包括杂芳基和非芳族的饱和和不饱和的杂环基。
杂环基一般是5或6元环，含有高达4个杂原子，选自氮、氧和硫，任选地和苯环稠合。作为杂芳基的例子，可特别提及的是衍生自以下的基团：噻吩、呋喃、吡咯、噻唑、噁唑、咪唑、异噻唑、异噁唑、吡唑、1，3，4-噁二唑、1，3，4-噻二唑、1，2，4-噁二唑、1，2，4-噻二唑、1，2，4-三唑、1，2，3-三唑、四唑、苯并[b]噻吩、苯并[b]呋喃、吲哚、苯并[c]噻吩、苯并[c]呋喃、异吲哚、苯并噁唑、苯并噻唑、苯并咪唑、苯并异噁唑、苯并异噻唑、吲唑、苯并噻二唑、苯并三唑、二苯并呋喃、二苯并噻吩、咔唑、吡啶、吡嗪、嘧啶、哒嗪、1，3，5-三嗪、1，2，4-三嗪、1，2，4，5-四嗪、喹啉、异喹啉、喹喔啉、喹唑啉、噌啉、1，8-二氮杂萘、1，5-二氮杂萘、1，6-二氮杂萘、1，7-二氮杂萘、2，3-二氮杂萘、吡啶并嘧啶、嘌呤或喋呤。
非芳族杂环一般是3-、5-、6-或7-元环，含有高达3个选自氮、氧和硫的杂原子，例如，环氧乙烷基、硫杂丙环基、噻唑啉基、二氧杂环戊烷基、1，3-苯并噁嗪基、1，3-苯并噻嗪基、吗啉-4-基、吡唑啉基、四氢噻吩砜基、二氢喹唑啉基、哌啶基、邻苯二甲酰亚氨基、四氢呋喃基、四氢吡喃基、吡咯烷基、吲哚啉基、2-氧代吡咯烷-3-基、2-氧代苯并噁唑啉-3-基、或四氢丫庚因基。
当在苯基或杂环基上有取代基时，它们可能是例如卤原子、CN、NO2、SF5、B(OH)2、三烷基甲硅烷基、酰基、O-酰基或基团E、OE或S(O)n，E如以上为R2所定义的或者是任选取代的氨基；或者在环上2个相邻的基团与和它们相连接的原子一起形成碳环或杂环(它们又可任选地以相似的方式被取代)。
术语“酰基”包括含硫或磷的酸残基和羧酸残基。例如-COR5、-COOR5、-CONR5R6、-CON(R5)OR6、-COONR5R6、-CON(R5)NR6R7、-COSR5、-CSSR5、-S(O)qR5、-S(O)2OR5、-S(O)qNR5R6、-P(＝L)(OR5)(OR6)、-COOR5，其中R5、R6和R7可以相同或不同，代表氢原子、若选取代的烷基、任选取代的环烷基、任选取代的环烯基、任选取代的炔基、任选取代的苯基或任选取代的杂环基，或者R5和R6，或R6和R7，与和它们连接的原子可形成环，q代表1或2，L代表O或S。
氨基可例如被1个或2个以下的基团取代：任选取代的烷基或任选取代的酰基或者2个取代基可形成环(优选5-7元环，它们可以被取代并可含有其它杂原子)，例如吗啉。
在式(I)的化合物中，优选具有至少一个以下特性的如下化合物：
---碘原子是在6位；
---R1代表C2-C4烷基；
---R2代表基团-W-R3，其中W代表氧，R3如上所定义。
最优选的式(I)化合物同时具有这三个特性，特别是这样的式(I)化合物，其中R3代表C1-C6烷基、C1-C6链烯基或C1-C6炔基或者其中R1是正丙基的式(I)化合物。
在式(I)化合物中，以举例的方式，可以说到以下的式(Ia)和(Ib)的化合物，但它们并不限制本发明的范围：
Figure C0281513700061
Figure C0281513700131
本发明化合物可以通过许多已知的方法制备，特别是在专利申请EP-861242中公开的那些方法。
在特别有利的方式中，式(I)化合物也可以按照以下方法制备：
这个方法构成本发明的另一个方面。
其它方法也可用来制备式(I)化合物，如与那些报道在以下文献中类似的方法：Chemistry and Industry，(1980)，116；J.Chem.Soc.Chem.Com.， 1，(1981)，282 and J.Org.Chem.，(1992)， 57，6502。
用于制备式(I)化合物的实际和一些中间体化合物可通过本领域已知的方法制备。
本发明的另一个方面涉及杀真菌组合物，包含：
(a)式(I)化合物：
其中，
碘原子取代在5，6，7或8位；
R1选自卤原子、取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、取代的或未取代的C1-C6炔基；
R2选自取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、取代的或未取代的C1-C6炔基、3-7元碳环或杂环(它们是取代的或未取代的，饱和的，不饱和的或芳族的)、卤原子、氰基、基团-W-R3；
W选自氧、硫或基团-NR4；
R3和R4可以相同或不同，各自独立选自氢原子、取代的或未取代的C1-C6烷基、取代的或未取代的C1-C6链烯基、和取代的或未取代的C1-C6炔基、烷氧基、氨基、3-7元碳环或杂环(它们是取代的或未取代的，饱和的，不饱和的或芳族的)，R3和R4可以一起形成5-7元杂环，它们可以是饱和的，不饱和的或芳族的，且还可以包含另一个杂原子；它们可能的几何和/或光学异构体(纯的形式或按任何比例的混合物形式，包括外消旋混合物)，它们可能的N-氧化物，与酸的加成盐，和它们可能的金属或准金属配合物；
(b)至少一种其它杀真菌化合物。
用于本发明组合物的优选的式(I)化合物是具有以下特征的至少一个的那些化合物：
---碘原子是在6位；
---R1代表C2-C4烷基；
---R2代表基团-W-R3其中W代表氧，R3如上定义。
用于本发明组合物的最优选的式(I)化合物同时具有这3个特征，特别是式(I)化合物，其中R3代表C1-C6烷基、C1-C6链烯基、或C1-C6炔基，或者是其中R1是正丙基的式(I)化合物。
具体可以提及具有以下化学名字的化合物：
2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮，
2-乙氧基-6-碘-3-丙基-苯并吡喃-4-酮，
6-碘-2-丙氧基-3-丙基-苯并吡喃-4-酮，
2-丁-2-炔氧基-6-碘-3-丙基-苯并吡喃-4-酮，
6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮，
2-丁-3-烯氧基-6-碘-3-丙基-苯并吡喃-4-酮，
3-丁基-6-碘-2-异丙氧基-苯并吡喃-4-酮，
6-碘-3-丙基-2-(四氢吡喃-4-基氧基)苯并吡喃-4-酮，
6-碘-3-丙基-2-(2，2，2-三氟乙氧基)-苯并吡喃-4-酮。
在本发明组合物中，优选使用的杀真菌化合物选自：
(b1)能抑制植物病原性真菌生物的线立体泛醌醇(ubiquinol)：正铁细胞色素c氧化还原酶呼吸链中的电子转移的化合物，具体有菌酯(strobilurin)衍生物，如腈嘧菌酯，地莫菌酯(dimoxystrobin)，法鲁克菌酯(fluoxastrobin)，亚胺菌，派克菌酯(pycoxystrobin)，派拉克菌酯(pyraclostrobin)，肟菌酯(trifloxystrobin)，咪唑菌酮，噁唑菌酮；
(b2)能抑麦角甾醇生物合成的化合物，具体有糠菌唑，氧唑菌，喹唑菌酮(fluquinconazole)，咪鲜安，派硫肯那唑(prothioconazole)，戊唑醇，三唑酮，喹唑菌酮，灭菌唑(triticonazole)。
其它可用于本发明组合物的优选化合物，可以提及的有环丙嘧啶，二硝巴豆酸酯，苯锈啶，丁苯吗啉，乙磷铝，异丙菌胺(iprovalicarb)，喹氧灵，螺噁茂胺。
作为式(I)化合物与一种或多种其它杀真菌化合物的具体联用，优选以下的联用：
式(I)化合物：                                                                  化合物(b)：
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   肟菌酯
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   Pyraclostrobin
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   Picoxystrobin
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   因迷菌酯(kresoxym-methyl)
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   喹唑菌酮
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   戊唑醇
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   Procloraz
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   Prothioconazole
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   三唑酮
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   唑菌醇
  6-碘-2-(1-甲基-丁氧基)-3-丙-苯并吡喃-4-酮   +   灭菌唑
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   氧唑菌
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   二硝巴豆酸酯
  6-碘-2-(1-甲-丁氧基)-3-丙-苯并吡喃-4-酮   +   螺噁茂胺
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   苯锈啶
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   丁苯吗啉
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   喹氧灵
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   环丙嘧啶
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   乙磷铝-Al
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   咪唑菌酮(Fenamidone)
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   异丙菌胺
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   +   Fluoxastrobin
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   肟菌酯
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   Pyraclostrobin
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   Picoxystrobin
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   亚胺菌
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   喹唑菌酮
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   戊唑醇
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   咪鲜安
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   Prothioconazole
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   三唑酮
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   唑菌醇
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   灭菌唑
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   氧唑菌
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   二硝巴豆酸酯
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   螺噁茂胺
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   苯锈啶
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   丁苯吗啉
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   喹氧灵
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   环丙嘧啶
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   乙磷铝
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   咪唑菌酮
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   异丙菌胺
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   Fluoxastrobin
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   肟菌酯喹唑菌酮
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   肟菌酯戊唑醇
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   肟菌酯咪鲜安
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   +   肟菌酯prothioconazole
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   肟菌酯螺噁茂胺
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin喹唑菌酮
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin戊唑醇
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin咪鲜安
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   FluoxastrobinProthioconazole
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin螺噁茂胺
  2-丁氧基-6-碘-3-丙基-苯并吡喃-4-酮   ++   乙磷铝咪唑菌酮
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   Trifloxysrtobin喹唑菌酮
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   肟菌酯戊唑醇
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   肟菌酯咪鲜安
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   肟菌酯Prothioconazole
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   肟菌酯螺噁茂胺
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin喹唑菌酮
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin戊唑醇
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin咪鲜安
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   FluoxastrobinProthioconazole
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   Fluoxastrobin螺噁茂胺
  6-碘-2-(1-甲基-丁氧基)-3-丙基-苯并吡喃-4-酮   ++   乙磷铝咪唑菌酮
使用本发明组合物，可能显示出增效作用。
为了使用，式(I)化合物和含有式(I)化合物与一种或多种其它杀真菌化合物联用的组合物通常与载体和农业上可接受的表面活性剂混合。
在本发明组合物中的载体或稀释剂可以是固体或液体，任选地和表面活性剂联用，例如分散剂、乳化剂或润湿剂。
合适的表面活性剂包括阴离子化合物如羧酸盐，例如长链脂肪酸的金属羧酸盐；N-酰基肌氨酸盐；磷酸与脂肪醇的单酯或二酯乙氧基化物或者所述酯的盐；脂肪醇硫酸酯如十二烷基硫酸酯钠、十八烷基硫酸酯钠、或十六烷基硫酸酯钠；乙氧基化的脂肪醇硫酸酯；乙氧基化的烷基苯酚硫酸酯；木素磺酸酯；石油磺酸酯；烷基芳基磺酸酯；如烷基苯磺酸酯、或低级烷基萘磺酸酯，例如丁基萘磺酸酯；磺化的萘-甲醛缩合物的盐；磺化的苯酚-甲醛缩合物的盐；或更复杂的磺酸盐，如酰胺磺酸盐，例如油酸与N-甲基牛磺酸的缩合产物的磺化产物或磺基琥珀酸二烷基酯，如琥珀酸二辛酯的磺酸钠。在非离子型的表面活性剂中，可提及脂肪酸酯、脂肪醇、脂肪酸酰胺、或脂族烷基或链烯基取代的苯酚与环氧乙烷的缩合产物；多元醇的醚的脂肪酸酯(例如失水山梨醇脂肪酸酯)；所述酯与环氧乙烷的缩合产物(例如聚氧乙烯失水山梨醇的脂肪酸酯)；乙烯和环氧丙烷的嵌段共聚物；炔二醇(如2，4，7，9-四甲基-5-癸炔-4，7-二醇，或乙氧基化的炔二醇。
在阳离子型表面活性剂中，可提及的有例如脂肪族单-、二-或多胺(乙酸盐、萘甲酸盐或油酸盐形式)；含氧的胺(如胺氧化物)或聚氧乙烯烷基胺；含酰胺键的胺(通过羧酸与二胺或多胺缩合制得)；或季铵盐。
本发明的组合物可采用农用化学品领域已知的任何形式，例如，溶液、分散液、水性乳液、粉状的粉剂、用于处理种子的配方、用于烟熏的配方；可分散的粉剂、可乳化的浓缩物或颗粒。而且，可以是可直接使用的形式、或是浓缩的形式或原组合物的形式，需要在使用前用适量的水或另一种稀释剂稀释。
在本发明的组合物中活性成分的浓度，当施用于植物时，优选在0.0001-1.0％重量的范围，特别是0.0001-0.01％重量的范围。在原组合物中，活性成分的量可作相当大的变化并可以是例如组合物的5-95％重量。
本发明的式(I)化合物，单独使用或以混合物形式使用，具有杀真菌剂的活性，特别是对抗植物的真菌病，例如粉状霉病和绒毛状霉病，特别是谷物白粉病(Blumeria graminis)、葡萄白粉病(Uncinula necator)、苹果白粉病(PodosphaeraLeucotrica)、葫芦白粉病(例如Erysiphe cichoracearum，Sphaerotheca fulginea，Erysiphe polygoni)、Solanaceae的白粉病(例如黄瓜白粉病)、水果和观赏植物的白粉病(例如梅白粉病)、爬山虎霜霉病(Plasmopara viticola)、水稻枯萎病(Pyricularia oryzae)、谷物色斑病(Pseudocercosporella herpotrichoides)、稻纹枯病(Pellicularia sasakii)、甘薯灰霉僵腐病(Botrytis cinerea)、棉立枯病(Rhizoctonia solani)、小麦叶锈病(Puccinia recondita)、马铃薯晚疫病(Phytophthora infestans)、苹果黑腥病(Venturia inaequalis)、颖枯病(Leptosphaeria nodorum)。
式(I)化合物对其它植物病原性真菌也是有活性的，包括白粉病、锈病的其它类型以及源自半知菌类(Deuteromycetes)，子囊菌(Ascomycetes)，藻状菌(Phycomycetes)和担子菌(Basidiomycetes)的一般病原体。
本发明式(I)化合物已经证明对谷物、葡萄藤、植物和果树、蔬菜作物和观赏植物的白粉病具有特别的活性。
本发明的另一个方面还涉及在已受感染或可能受感染的部位防治作物的植物病原性真菌的方法，该方法包含向所述的部位施用至少一种式(I)的化合物，单独施用或与一种或多种如上所述的其它杀真菌化合物在本发明的组成范围内联用。
在本发明的方法中，式(I)的化合物一般施用于种子、植物或施用于它们生长或将要生长的地方。因此，可在播种之前、之时或之后将该化合物直接施用到土壤中，使得存在于土壤中的活性成分能够防治可能攻击种子的植物病原性真菌的生长。在直接处理土壤时，可将活性物质以任一方式施用，使得它能与土壤紧密混合，例如通过喷洒、将土壤以颗粒的形式撒播在地上、或在播种时将活性成分和种子混合在一起加在播种机中。合适的施用剂量是每公顷5-1000克，优选每公顷10-500克。
另一种方法包括将活性成分直接施用在植物上，例如喷洒或撒粉，在植物病原性真菌开始出现在植物上时，或者在所述真菌出现之前作为预防措施，或预防性或治疗性地施用。在这些情况的每一种，优选的方法是叶面喷洒。一般地说，重要的是在植物生长的第一阶段得到良好的对植物病原性真菌的防治，这些阶段恰好是植物可能受到最严重伤害的时刻。有时在栽种前或栽种中处理植物的根部是有益的，例如把根部浸在包含式(I)化合物的组合物中。
本发明地用以下实施例来说明但不受其限制。
试验实施例1
试验化合物对白粉病(Blumeria graminis)的活性。
冬小麦(阿波罗变种)种在法国(Marne县)1米2土地中，比例为200千克/公顷(土壤：有色的黑色石灰土)深度为3厘米。本发明化合物分2部分施用在小麦植物上：施用A在1厘米穗期，施用B在第二可见叉期。每次施用都通过将化合物的水溶液以每公顷125克活性成分的剂量喷洒。
在使用A期间，对白粉病真菌的攻击强度为大约总叶片体积的3％。
在施用B的52天后，通过评价第二叶(从穗中记数)的受感染表面的面积的百分数，进行攻击强度试验。
列在表1的结果是用以下本发明化合物得到的：
化合物1：2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮
化合物2：6-碘-2-丙氧基-3-丙基苯并吡喃-4-酮
化合物3：2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮
对照：未处理的植物和化合物B：喹氧灵(商品名Fortress)。
表1(攻击强度试验)
  化合物   每(第二)叶受感染表面面积％
  1   0.56
  2   2.53
  3   2.51
  对照   30.47
  A   6.47
  B   4.91
在相同的条件下，通过评价被白粉病菌攻击的第二叶的百分数进行攻击程度的试验。
得到的结果列在表2。
表2(攻击程度试验)
  化合物   受攻击的第二叶％
  1   28.0
  3   54.0
  对照   98.7
  A   78.7
  B   73.3
这2个试验的结果表明，本发明式(I)的碘化的化合物与未处理的对照相比，是有活性的，也比商品参照物活性更高。
试验实施例2
本实施例说明式(I)化合物对于strobilurin衍生物抗性的病原性菌株的生物学效果。
试验在温室中进行。
抗性菌株是在2001年在德国北部Bremen地区的用pyraclostrobin和picoxystrobin处理过的地方分离并取样的。这些菌株通过它们对这些strobilurin型化合物的抗性表征的。它们然后被保持在受控的环境小室中在小麦植株(Kanzler变种)上用肟菌酯处理。
用在水中稀释到相当于250升/公顷的体积的溶液喷洒在小麦植物上。24小时后，用白粉病(Blumeria graminis f.sp.tritici)接种在植物上。接种13天后对每棵植物评价疾病的程度。
得到的结果收集在表3中，该结果表明所用的化合物能够完全防治所处理的菌株。这些结果可应用于大田的条件。
表3
  施用的化合物   施用量(克/公顷)   感染白粉病叶子的百分数(％)
  未处理的对照植物    -   100
  肟菌酯(EC，125g/l-Twist)   31   100
  62   100
  125   100
  250   100
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮(SC，500g/l)   31   0
  62   0
试验实施例3
本实施例说明本发明化合物以与strobilurin类化合物的混合物的形式使用得到增效作用，所述strobilurin类化合物具体为肟菌酯，三唑，特别是喹唑菌酮。本发明化合物是在温室中在预防的条件下进行试验的。该增效作用用感染谷物的主要疾病而证明，具体是小麦和大麦的白粉病(Blumeria graminis f.sp.Tritici和Blumeria graminis f.sp.hordei)、小麦叶锈病(Puccinia recondita)和小麦颖枯病(Septoria tritici和Septoria nodorum)。
表4为活性成分组合的评价。
表4
  活性成分   比例   施用剂量(克/公顷)
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮(SC，500g/l) -   1.5，3，4，6，8，12，16，25，31，50，62
  喹唑菌酮(SC at 100g/lFlamenco)   -   3，6，8，12，16，25，31，50，62，125
  肟菌酯(WG at 500g/kg-Flint)   -   4，8，16，31，62，125
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮(SC at 500g/l)+肟菌酯(WG，500g/kg)   1/11/2.51/5
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮(SC at 500g/l)+喹唑菌酮(SC at 100g/l)   1/11/21/5
Epoxyconazole和亚胺菌(SC 125g/l+125g/l-Ogam)的混合物用作参照物，以62+62克/公顷和125+125克/公顷的推荐施用剂量使用。
用以下方式将化合物和混合物喷洒在小麦植物上：
---2次重复，
---施用体积相当于250升/公顷。(译者注：原文如此，似应为克/公顷)
施用后的第二天，用小麦白粉状病(Blumeria graminis f.sp.Tritici)、小麦叶锈病(Puccinia recondita)、小麦颖枯病(Septoria tritici和Septorianodorum)接种小麦和用白粉病(Blumeria graminis f.sp.hordei)接种大麦。
一旦发病，通过测定每盆的发病程度来进行评价。
增效作用的水平用Colby公式计算，以便计算理论果效并与观察到的效果进行比较：
A+B的理论效果＝A的效果(％)+B的效果(％)-[A的效果(％)×B的效果(％)/100]
如果观察的效果高于计算的功效，就证明了增效作用；如果相等，就证明了相加的效果；如果较低，则证明了拮抗作用。
表5总结了本发明式(I)化合物和喹唑菌酮的混合物用于防治小麦白粉病的结果。
表5
  活性成分   施用剂量(克/公顷)   比例   观察效果(％)   理论效果(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   6   -   25   -   -
  喹唑菌酮   6   -   0   -   -
  12   -   0   -   -
  31   -   0   -   -
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+喹唑菌酮   6+6   1/1   93   25   +68
  6+12   1/2   90   25   +65
  6+31   1/5   95   25   +70
表6总结了本发明式(I)化合物和喹唑菌酮的混合物用于防治大麦白粉病的结果。
表6
  活性成分   施用剂量(克/公顷)   比例   观察到的功效(％)   理论功效(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   12   -   50   -   -
  喹唑菌酮   12   -   25   -   -
  25   -   25   -   -
  62   -   75   -   -
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+喹唑菌酮   12+12   1/1   90   62.5   +28
  12+25   1/2   95   62.5   +33
  12+62   1/5   98   87.5   +11
表7总结了本发明式(I)化合物和喹唑菌酮的混合物用于防治小麦褐锈病的结果。
表7
  活性成分   施用剂量(克/公顷)   比例   观察到的功效(％)   理论功效(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   50   -   0   -   -
  喹唑菌酮   100   -   60   -   -
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+喹唑菌酮   50+100   1/2   90   60   +30
表8总结了本发明式(I)化合物和喹唑菌酮的混合物用于控制小麦颖片污斑病(Septoria tritici)的结果。
表8
  活性成分   施用剂量(克/公顷)   比例   观察效果(％)   理论效果(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   50   -   0   -   -
  喹唑菌酮   100   -   60   -   -
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+喹唑菌酮   50+100   1/2   90   60   +30
表9总结了本发明式(I)化合物和喹唑菌酮的混合物用于防治小麦颖枯病(Septoria nodorum)的结果。
表9
  活性成分   施用剂量(克/公顷)   比例   观察效果(％)   理论效果(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   50   -   0   -   -
  喹唑菌酮   100   -   75   -   -
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+喹唑菌酮   50+100   1/2   95   75   +20
这些结果证明了式(I)化合物和喹唑菌酮的混合物在1/1、1.2或1/5的比例对小麦和大麦粉状霉病、小麦褐锈病和颖片污斑病的高度协同作用。这些混合物能够以农学的施用剂量获得优异的功效结果。
表10总结了本发明式(I)化合物和肟菌酯的混合物用于防治小麦白粉病的结果。
表10
  活性成分   施用剂量(克/公顷)   比例   观察效果(％)   理论效果(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   6   -   25
  16   -   50   -   -
  25   -   75
  Trilfoxystrobin   16   -   30   -   -
  31   -   40
  62   -   50
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+肟菌酯   16+16   1/1   95   65   +30
  25+62   1/2.5   95   87.5   +8
  6+31   1/6   85   55   +30
表11总结了本发明式(I)化合物和肟菌酯的混合物用于防治大麦白粉病的结果。
表11
  活性成分   施用剂量(克/公顷)   比例   观察效果(％)   理论效果(％)   增效水平
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮   16   -   50   -   -
  25   -   75
  Trilfoxystrobin   16   -   0   -   -
  62   -   0
  2-乙氧基-6-碘-3-丙基苯并吡喃-4-酮+肟菌酯   16+16   1/1   75   50   +25
25+62 1/2.5 85 75 +10
这些结果证明了式(I)化合物和肟菌酯的混合物在1/1、1/2.5或1/5的比例对小麦和大麦白粉病(对strobilurin类化合物敏感的菌株)的高度增效作用。

Claims (11)

1.一种杀真菌组合物，它包含：
(a)式(I)化合物：
Figure C028151370002C1
其中：
碘原子取代在5、6、7或8位上；
R1是C1-C6烷基；
R2是C1-C6烷氧基或C1-C6烷硫基；
(b)至少一种其它杀真菌化合物，它选自：
(b1)能抑制植物病原性真菌生物的线立体泛醌醇：正铁细胞色素c氧化还原酶呼吸链中的电子转移的化合物，或
(b2)能抑制麦角甾醇生物合成的化合物；
组分(a)与(b)的重量比为1∶1、1∶2、1∶2.5、1∶5或1∶6。
2.如权利要求1所述的组合物，其特征在于式(I)化合物中碘原子在6位上。
3.如权利要求1或2所述的组合物，其特征在于式(I)化合物中R2是C1-C6烷氧基。
4.如权利要求1或2所述的组合物，其特征在于式(I)化合物中R1是正丙基。
5.如权利要求1或2所述的组合物，其特征在于所述(b1)化合物是菌酯衍生物、咪唑菌酮或噁唑菌酮。
6.如权利要求5所述的组合物，其特征在于所述菌酯衍生物选自腈嘧菌酯，地莫菌酯，法鲁克菌酯，亚胺菌，派克菌酯，派拉克菌酯，肟菌酯。
7.如权利要求1或2所述的组合物，其特征在于所述(b2)化合物是三唑类杀真菌化合物。
8.如权利要求7所述的组合物，其特征在于所述三唑类化合物选自糠菌唑、氧唑菌、氟喹唑，咪鲜安、派硫肯那唑，戊唑醇，三唑酮、三唑醇、灭菌唑。
9.如权利要求1或2所述的组合物，其特征在于化合物(b)选自嘧菌环胺，二硝巴豆酸酯，苯锈啶，丁苯吗啉，乙磷铝，异丙菌胺，苯氧喹啉，螺环菌胺。
10.在被感染或可能被感染处控制植物病原性真菌的方法，它包括对所述被感染或可能被感染处施用如权利要求1-9中任一项所述的组合物。
11.如权利要求1-9中任一项所述的组合物在控制植物病原性真菌中的用途。
CNB028151372A 2001-08-03 2002-07-31 具有杀真菌活性的碘代苯并吡喃－4－酮衍生物 Expired - Fee Related CN1261426C (zh)

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