CN104520273A - 2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 - Google Patents
2-氨基烟酸酯衍生物及以其为有效成分的灭菌剂 Download PDFInfo
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- CN104520273A CN104520273A CN201380035233.9A CN201380035233A CN104520273A CN 104520273 A CN104520273 A CN 104520273A CN 201380035233 A CN201380035233 A CN 201380035233A CN 104520273 A CN104520273 A CN 104520273A
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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Abstract
本发明提供一种以2-氨基烟酸酯衍生物为有效成分的灭菌剂。本发明的有效成分由以下的式[I]表示。(式中，R1表示氢原子或C1～C4的烷基，R2表示氢原子或C1～C4的烷基，R1和R2可以相互键合而形成亚烷基链，R3表示氢原子、C1～C4的烷基，R4表示氢原子、氰基或C1～C4的烷基，R5及R6相互独立地表示氢原子、卤原子、C1～C4的烷基、C1～C4的烷氧基、C1～C4的烷基硫基、C1～C4的烷基亚硫酰基、C1～C4的烷基磺酰基、硝基、氰基、C1～C4的卤烷基、C1～C4的卤烷氧基或C1～C4的卤烷基硫基，A及B相互独立地表示次甲基(CH)或氮原子)。
Description
技术领域
本发明涉及一种2-氨基烟酸酯衍生物及以其为有效成分含有的灭菌剂。
背景技术
在农业和园艺领域中，开发了以各种病原菌的防除为目的的各种灭菌剂，供于实用。
但是，目前通用的农药未必可以说满足其效果及光谱、残效性等，进而施用次数和施用药量的降低等要求。此外，对目前通用的农药的抵抗性发达的病原菌的出现也成为问题。例如，在蔬菜和果树、花卉、茶、糊米类及水稻等栽培中，对例如三唑类、咪唑类、嘧啶类、苯并咪唑类、二羧基酰亚胺类、苯基酰胺类、嗜球果伞素类等各种类型的灭菌剂的抵抗性发达的各种病原菌在各地出现，这些抵抗性病原菌的防除每年都很困难。因此，经常期望相对于对目前通用的农业和园艺用灭菌剂的抵抗性发达的各种病原菌也以低药量显示充分的防除效果、而且对环境的不良影响小的、新型的农药的出现。
提出了各种用于适应于这些要求的新的灭菌剂，但未必适应于上述要求。
在专利文献1中公开有含有具有灭菌活性的以下结构的甲酰胺衍生物。但是，专利文献1中记载的化合物在吡啶环的3位上具有甲酰胺键，并不具有酯键。
专利文献2中，将在吡啶环的2位上具有氨基的以下酯衍生物作为反应中间体(265页实施例35化合物编号757)公开。但是，该化合物为具有甲氧基的化合物，并不具有苯氧基。另外，该化合物归根结底只不过作为专利文献2的医药活性化合物的制造中间体公开，专利文献2中对灭菌活性完全没有记载。
专利文献3～6中，作为具体合成的化合物，对如下所述的在吡啶环的2-位上不具有氨基的酯衍生物公开。作为其代表例，可例示以下的化合物。公开有这些化合物具有杀虫活性或除草活性，但具有灭菌活性则完全没有报道。
专利文献3公开有以下的化合物(43页化合物编号1.59)。但是，专利文献3没有公开与作为杀虫剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献4公开有以下的化合物(33页化合物270及271)。但是，专利文献4没有公开与作为杀虫剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献5公开有以下的化合物(78页的化合物编号1.3717)。但是，专利文献5没有公开与作为除草剂的用途有关、在吡啶环的2位上具有氨基的化合物。
专利文献6公开有以下的化合物(42页的化合物编号229)。但是，专利文献6没有公开与作为除草剂的用途有关、在吡啶环的2位上具有氨基的化合物。
另外，专利文献7或专利文献8中，作为具有灭菌活性的具体的化合物，公开有以下的化合物。
具体而言，专利文献7公开有以下的化合物(50页的化合物编号48)。但是，专利文献7中没有公开在吡啶环的2位上具有氨基的化合物。
另外，专利文献8公开有以下的化合物(40页的化合物编号22)。但是，专利文献8没有公开在吡啶环的2位上具有氨基的化合物。
另一方面，专利文献9～14具体地公开有具有医药活性的以下的化合物。详述为，专利文献9公开有以下的化合物(42页的实施例186)。但是，专利文献9没有公开在吡啶环的2位上具有氨基的化合物。另外，专利文献9的化合物只不过作为医药活性物质公开。
另外，专利文献10具体公开有以下的化合物(32页工序3的反应式右侧的化合物)。但是，该化合物只不过作为反应中间体被公开，另外专利文献10没有公开在吡啶环的2位上具有氨基的化合物。
专利文献11公开有以下的化合物作为丙基-3-烟酰(17页)。但是，专利文献11没有公开在吡啶环的2位上具有氨基的化合物。另外，专利文献11的化合物只不过作为医药活性物质公开。
专利文献12公开有以下的化合物(51页的E工序1)。但是，专利文献11仅将该化合物作为中间体公开，没有公开在吡啶环的2位上具有氨基的化合物。另外，专利文献11的化合物只不过作为医药活性物质公开。
专利文献13公开有以下的化合物(56页(I-17b))。但是，专利文献13没有公开在吡啶环的2位上具有氨基的化合物。另外，专利文献13的化合物只不过作为医药活性物质公开。
专利文献13公开有以下的化合物(93页、合成方案)。但是，专利文献13中，该化合物仅作为中间体公开，没有公开在吡啶环的2位上具有氨基的化合物。另外，专利文献13的化合物只不过作为医药活性物质公开。
非专利文献1涉及一种作为查格斯氏病的治疗剂使用的医药活性化合物。非专利文献1就具有苯氧基苄氧基骨架的医药活性化合物进行了公开。但是，关于在该骨架上插入有2-氨基烟酸的化合物则完全没有公开。
现有技术文献
专利文献
专利文献1：日本特开2010-083861号公报
专利文献2：WO2008-082490号小册子
专利文献3：WO2004-056735号小册子
专利文献4：WO2002-002515号小册子
专利文献5：WO2000-015615号小册子
专利文献6：日本特开2004-051628号公报
专利文献7：WO1994-029267号小册子
专利文献8：WO1998-033772号小册子
专利文献9：EP1995-650961号小册子
专利文献10：WO1998-057946号小册子
专利文献11：WO2003-101980号小册子
专利文献12：WO2007-133561号小册子
专利文献13：WO2010-029461号小册子
专利文献14：WO2011-083304号小册子
非专利文献
非专利文献1：Journal of Medicinal Chemistry，43卷，1826页(2000)
发明内容
发明要解决的课题
本发明提供一种对各种菌类的防除有用的新的物质，特别提供一种相对于现有的灭菌剂显示抵抗性、同时相对于各种菌类也显示高的防除效果、进而以低药量产生效果、因此残留毒性和环境污染等问题得到减轻的安全性高的物质。
解决课题的技术方案
本发明人等为了解决上述的课题进行了潜心研究，结果发现，下式规定的2-氨基烟酸酯衍生物为具有可以适应于上述要求的特性的化合物，直至完成了本发明。
即，本发明涉及一种2-氨基烟酸酯衍生物(以下，也称为“本发明的化合物”)及含有其作为有效成分的灭菌剂，所述2-氨基烟酸酯衍生物用下式[I]表示：
(式中，R1表示氢原子或C1～C4的烷基，
R2表示氢原子、C1～C4的烷基，或R1和R2相互键合，表示
或
R3表示氢原子、C1～C4的烷基，
R4表示氢原子、氰基或C1～C4的烷基，
R5及R6相互独立地表示氢原子、卤原子、C1～C4的烷基、C1～C4的烷氧基、C1～C4的烷基硫基、C1～C4的烷基亚硫酰基、C1～C4的烷基磺酰基、硝基、氰基、C1～C4的卤烷基、C1～C4的卤烷氧基或C1～C4的卤烷基硫基，
A及B相互独立地表示次甲基(CH)或氮原子。)
发明效果
本发明的化合物相对于各种菌类显示优异的效果。
具体实施方式
以下，对本发明详细地说明。
式[I]表示的本发明的化合物中，作为R1、R2、R3、R5及R6表示的C1～C4的烷基，可列举例如：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基等。作为R5及R6表示的卤原子，可列举例如：氟原子、氯原子、溴原子、碘原子。
作为R5及R6表示的C1～C4的烷氧基，可列举例如：甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基。
作为R5及R6表示的C1～C4的烷基硫基，可列举例如：甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基。
作为R5及R6表示的C1～C4的烷基亚硫酰基，可列举例如：甲基亚硫酰基、乙基亚硫酰基、正丙基亚硫酰基、异丙基亚硫酰基、正丁基亚硫酰基、异丁基亚硫酰基、仲丁基亚硫酰基、叔丁基亚硫酰基。
作为R5及R6表示的C1～C4的烷基磺酰基，可列举例如：甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基。
作为R5及R6表示的C1～C4的卤烷基，可列举例如：单氟甲基、二氟甲基、三氟甲基、单氯甲基、二氯甲基、三氯甲基、单溴甲基、二溴甲基、三溴甲基、1-氟乙基、2-氟乙基、2，2-二氟乙基、2，2，2-三氟乙基、2-氯-2，2-二氟乙基、1-氯乙基、2-氯乙基、2，2，-二氯乙基、2，2，2-三氯乙基、1-溴乙基、2-溴乙基、2，2-二溴乙基、2，2，2-三溴乙基、2-碘乙基、五氟乙基、3-氟丙基、3-氯丙基、3-溴丙基、1，3-二氟-2-丙基、3，3，3-三氟丙基、1，3-二氯-2-丙基、1，1，1-三氟-2-丙基、1-氯-3-氟-2-丙基、1，1，1，3，3，3-六氟-2-丙基、1，1，1，3，3，3-六氟-2-氯-2-丙基、2，2，3，3，3-五氟丙基、七氟异丙基、七氟-正丙基、4-氟丁基、4，4，4-三氟丁基、九氟-正丁基、九氟-2-丁基。
作为R5及R6表示的C1～C4的卤烷氧基，可列举例如：单氟甲氧基、二氟甲氧基、三氟甲氧基、单氯甲氧基、二氯甲氧基、三氯甲氧基、单溴甲氧基、二溴甲氧基、三溴甲氧基、1-氟乙氧基、2-氟乙氧基、2，2-二氟乙氧基、2，2，2-三氟乙氧基、2-氯-2，2-二氟乙氧基、1-氯乙氧基、2-氯乙氧基、2，2，-二氯乙氧基、2，2，2-三氯乙氧基、1-溴乙氧基、2-溴乙氧基、2，2-二溴乙氧基、2，2，2-三溴乙氧基、2-碘乙氧基、五氟乙氧基、3-氟丙氧基、3-氯丙氧基、3-溴丙氧基、1，3-二氟-2-丙氧基、3，3，3-三氟丙氧基、1，3-二氯-2-丙氧基、1，1，1-三氟-2-丙氧基、1-氯-3-氟-2-丙氧基、1，1，1，3，3，3-六氟-2-丙氧基、1，1，1，3，3，3-六氟-2-氯-2-丙氧基、2，2，3，3，3-五氟丙氧基、七氟异丙氧基、七氟-正丙氧基、4-氟丁氧基、4，4，4-三氟丁氧基、九氟-正丁氧基、九氟-2-丁氧基。
作为R5及R6表示的卤烷基硫基，可列举例如：单氟甲基硫基、二氟甲基硫基、三氟甲基硫基、单氯甲基硫基、二氯甲基硫基、三氯甲基硫基、单溴甲基硫基、二溴甲基硫基、三溴甲基硫基、1-氟乙基硫基、2-氟乙基硫基、2，2-二氟乙基硫基、2，2，2-三氟乙基硫基、2-氯-2，2-二氟乙基硫基、1-氯乙基硫基、2-氯乙基硫基、2，2，-二氯乙基硫基、2，2，2-三氯乙基硫基、1-溴乙基硫基、2-溴乙基硫基、2，2-二溴乙基硫基、2，2，2-三溴乙基硫基、2-碘乙基硫基、五氟乙基硫基、3-氟丙基硫基、3-氯丙基硫基、3-溴丙基硫基、1，3-二氟-2-丙基硫基、3，3，3-三氟丙基硫基、1，3-二氯-2-丙基硫基、1，1，1-三氟-2-丙基硫基、1-氯-3-氟-2-丙基硫基、1，1，1，3，3，3-六氟-2-丙基硫基、1，1，1，3，3，3-六氟-2-氯-2-丙基硫基、2，2，3，3，3-五氟丙基硫基、七氟异丙基硫基、七氟-正丙基硫基、4-氟丁基硫基、4，4，4-三氟丁基硫基、九氟-正丁基硫基、九氟-2-丁基硫基。
另外，R4表示氢原子、氰基或C1～C4的烷基，作为C1～C4的烷基，可列举：R1、R2、R3、R5及R6表示的烷基。
本发明的化合物为文献未记载的新型化合物，例如，可以由公知的起始化合物，按照下述反应式制造。
反应式
(式中，R1、R2、R3、R4、R5、R6、A及B如前述式[I]中所定义。)
可以通过使通式[II]表示的2-氨基烟酸衍生物和通式[III]表示的醇衍生物在缩合剂及碱存在下，在惰性溶剂中反应来制造通式[I]表示的本发明的2-氨基烟酸酯衍生物。
在此，化合物[II]及[III]为已经公知的化合物，或只要是本领域技术人员，就可以由公知化合物直接合成的化合物。
本反应中的反应温度通常为-20℃～120℃，优选为0℃～40℃的范围，就反应时间而言，在通常0.2小时～24小时，优选1小时～5小时的范围内进行。通式[III]表示的苯氧基己醇衍生物相对于通式[II]表示的2-氨基烟酸衍生物在通常1～5倍摩尔，优选1～1.5倍摩尔的范围内使用。
作为本反应中使用的缩合剂，可以例示例如：氰基磷酸二乙酯(DEPC)和羰基二咪唑(CDI)、1，3-二环己基碳二亚胺(DCC)、1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐、氯甲酸酯类、碘化2-氯-1-甲基吡啶鎓等，就其使用量而言，相对于通式[II]表示的2-氨基烟酸衍生物在通常1～3倍摩尔，优选1～1.5倍摩尔的范围内使用。
作为碱，可以列举例如：氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾等无机碱类；醋酸钠、醋酸钾等醋酸盐类；叔丁醇钾、甲醇钠、乙醇钠等金属醇盐类；三乙基胺、二异丙基乙基胺、1，8-二氮杂双环[5，4，0]十一碳-7-烯等叔胺类；吡啶、二甲基氨基吡啶等含氮芳香族化合物等。就碱的量而言，相对于通式[II]表示的2-氨基烟酸衍生物，在通常1～10倍摩尔，优选1～2倍摩尔的范围内使用。
本反应可以使用溶剂，也可以不使用，在使用溶剂的情况下，作为溶剂，只要不显著地阻碍本反应，就没有特别限制地使用各种溶剂，作为这样的溶剂，可以优选列举例如：二甲基醚、二乙基醚、二异丙基醚、二丁基醚、四氢呋喃、二噁烷等链状或环状醚类；苯、甲苯、二甲苯等芳香族烃类；二氯甲烷、氯仿、四氯化碳等卤代烃类；乙腈等腈类；醋酸甲酯、醋酸乙酯、醋酸丁酯等酯类；N，N-二甲基甲酰胺、N，N-二甲基乙酰胺、二甲基亚砜、1，3-二甲基-2-咪唑烷酮等极性溶剂，这些惰性溶剂可以单独使用，或2种以上混合使用。
反应后，目标化合物可以由含有其的反应系统，利用常规方法容易地分离，例如，可以用再结晶和柱色谱法等通过精制等来制备目标化合物。
本反应中所使用的通式[II]表示的2-氨基烟酸衍生物可以根据例如日本特开2010-083861号公报(专利文献1)中所记载的方法，由公知化合物直接合成。
本反应中所使用的通式[III]表示的醇衍生物可以根据例如Journal ofMedicinal Chemistry，43卷，1826页(2000)(非专利文献1)中所记载的方法，由公知化合物直接合成。
本发明的化合物可以为了防除诸如以下的果树类的病害而使用：鳄梨、杏、无花果、伊予柑、梅子、温州蜜柑、黄桃、牡蛎、臭橙、猕猴桃、李子、西洋梨、桶柑、凸顶柑(でこぽん)、梨、夏季蜜柑、油桃、八朔、番木瓜、枇杷、葡萄、朱栾、芒果、桃、柚子、苹果、柠檬等；谷类、例如大麦、小麦、水稻、玉米、薏苡、黑麦、陆稻等；薯类、例如甘薯、马铃薯、芋头、山芋等；蔬菜类、例如小豆、草莓、菜豆、豌豆、秋葵、芜菁、南瓜、甘蓝、黄瓜、牛蒡、豇豆、越瓜、西瓜、芹菜、蚕豆、萝卜、大豆、洋葱、甜菜、辣椒、冬瓜、番茄、茄子、苦瓜、胡萝卜、葱、白菜、西芹、青椒、丝瓜、甜瓜、莴苣等；特用作物、例如甘蔗、矮草、烟草、茶、油菜籽、爆裂型玉米(ポップ)等；花卉类、例如八仙花、香石竹、大丁草、勋章菊、菊花、金鱼草、金盏花、鼠尾草、满天星、香豌豆花、匙叶草属植物(Statice)、非洲堇、大丽花、梯牧草、飞燕草、洋桔梗、马鞭草、向日葵、荆棘类、秋海棠、矮牵牛、猩猩木、紫丁香、龙胆、迷迭香等；树木类、例如金合欢树类、枫树、橡树类、桂树、桐、榉、樱花类、臀鳍类、杜鹃类、山茶类、栎类、赤杨类、垂柳类。
作为成为对象的病害，可列举植物寄生性的丝状菌、细菌及放线菌类，具体而言，可列举：稻瘟病(Pyricularia oryzae)、胡麻叶斑病(Cochliobolusmiyabeanus)、纹枯病(Rizoctonia solani)、稻谷枯细菌病(Burcholderiaglumae)、白叶枯病(Xanthomonas oryzae pv.oryzae)、褐条病(Acidovoraxavenae subsp.avenae)、内颖褐变病(Erinia ananas)、叶梢褐变病(Pseudomonasfuscovaginae)、立枯细菌病(Burkholderia plantarii)等；麦类的白粉病(Erysiphe graminis)、赤霉病(Gibberella zeae)、赤锈病(Puccinia striiformis，P.graminis，P.recondita，P.hordei)、雪腐病(Typhula sp.，Micronectriellanivalis)、裸黑穗病(Ustilago tritici，U.nuda)、网腥黑穗病(Tilletia caries)、眼纹病(Pseudocercosporella herpotrichoides)、云形病(Rhynchosporium secalis)、叶枯病(Septoria tritici)、颖枯病(Leptosphaeria nodorum)、网斑病(Pyrenophora teres)、
豹纹病(Helminthosporium zonatum Ikata)、黑节病(Pseudomonassyringae pv.japonica)等；柑橘类的黑点病(Diaporthe citri)、柑桔疮痂病(Elsinoe fawcetti)、果实腐败病(Penicillium digitatum，P.italicum)、褐色腐败病(Phytophthora citrophthora，P.nicotianae)、黑星病(Phyllostictina citricarpa)、溃疡病(Xanthomonas campestris pv.citri)等；苹果的念珠菌病(Moniliniamali)、腐烂病(Valsa mali)、白粉病(Podosphaera leucotricha)、斑点落叶病(Alternaria mali)、黑星病(Venturia inaequalis)、黑点病(Mycospherella pomi)、炭疽病(Colletotrichum acutatum)、轮纹病(Botryosphaeria berengeriana)、赤星病(Gymnosporangium yamadae)、灰星病(Monilinia ffucticola)等；梨的黑星病(Venturia nashicola，V.pirina)、黑斑病(Alternaria kikuchiana)、蛙眼病(Gymnosporangium haraeanum)、灰星病(Monilinia fructigena)等；桃的灰星病(Monilinia fructicola)、黑星病(Cladosporium carpophilum)、
桑干枯病(Phomopsis sp.)、穿孔细菌病(Xanthomonas campestris pv.pruni)等；葡萄的黑痘病(Elinoe ampelina)、晚腐病(Colletotrichum acutatum)、白粉病(Uncinula necator)、锈病(Phakopsora ampelopsidis)、黑腐病(Guignardia bidwellii)、霜霉病(Plasmopara viticola)、灰星病(Moniliniafructigena)、黑星病(Cladosporium viticolum)、灰色霉病(Botrytis cinerea)、根癌瘤细菌病(Agrobacterium vitis)等；牡蛎的炭疽病(Gloeosporium kaki)、落叶病(Cercospora kaki，Mycoshaerella nawae)等；
大豆的紫斑病(Cercospora kikuchii)、黑痘病(Elsinoe glycines)、黑点病(Diaporthe phaseolorum var.sojae)、斑点细菌病(Pseudomonas savastanoi pv.glycinea)、细菌性斑疹病(Xanthomonas campestris pv.glycines)等；菜豆的炭疽病(Colletotrichum lindemthianum)、环孔枯萎病(Pseudomonas savastanoi pv.phaseolicola)、细菌性斑疹病(Xanthomonas campestris pv.phaseoli)等；落花生的黑斑病(Cercospora personata)、褐斑病(Cercospora arachidicola)等；豌豆的白粉病(Erysiphe pisi)等；瓜类的炭疽病(Colletotrichum lagenarium)、白粉病(Sphaerotheca fuliginea，Oidiopsis taurica)、蔓枯病(Didymella bryoniae)、蔓割病(Fusarium oxysporum)、霜霉病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.)、斑点细菌病(Pseudomonassyringae pv.lachrymans)、褐斑细菌病(Xanthomonas campestris pv.cucuribitae)等；番茄的轮纹病(Alternaria solani)、叶霉病(Cladosporiumfulvum)、疫病(Phytophthora infestans)、青枯病(Ralstonia colanacearum)、
溃疡病(Clavibacter michiganense subsp.michiganense)、茎坏疽病(Pseudomonas corrugata)、软腐病(Erwinia carotovora subsp.carotovora)等；茄子的褐纹病(Phomopsis vexans)、白粉病(Erysiphe cichoracearum)、青枯病(Ralstonia colanacearum)等；油菜科蔬菜的黑斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、黑腐病(Xanthomonas campestris pv.campestris)、软腐病、腐败病(Pseudomonas syringae pv.marginalis)等；葱的锈病(Puccinia allii)等；马铃薯的夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、叶腐病菌(Rhizoctonia solani)、软腐病、黑脚病(Erwinia carotovora subsp.atroseptica)、青枯病(Ralstonia colanacearum)、柑桔疮痂病(Streptomyces scabies，Streptomyces acidiscabies)等；草莓的白粉病(Sphaerotheca humuli)、青枯病(Ralstonia colanacearum)、芽枯细菌病(Pseudomonas marginalis pv.marginalis)、角斑细菌病(Xanthomonascampestris，Xanthomonas fragariae)等；茶的网饼病(Exobasidiumreticulatum)、白星病(Elsinoe leucospila)、野火病(Pseudomonas syringae pv.theae)、立枯病(Ralstonia solanacearum)、溃疡病(Xanthomonas campestris pv.theicola)等；
烟草的赤星病(Alternaria longipes)、白粉病、炭疽病(Colletotrichumtabacum)、霜霉病(Peronospora tabacina)、疫病(Phytophthora nicotianae)、空洞病(Erwinia carotovora subsp.carotovora)等；甜菜的褐斑病(Cercosporabeticola)、苗立枯病(Aphanomyces cochliodes)等；胡萝卜的黑叶枯病(Alternaria dauci)、瘤病(Rhizobacter dauci)、链霉菌柑桔疮痂病(Streptomycesscabies)、荆棘的黑星病(Diplocarpon rosae)、白粉病(Sphaerotheca pannosa)、根癌瘤病(Agrobacterium tumefaciens)等；菊花的褐斑病(Septoriachrysanthemi-indici)、白锈病(Puccinia horiana)、根癌瘤病等；各种作物的灰色霉病、菌核病(Sclerotinia sclerotiorum)等，但不一定限定于在此记载的菌类。
本发明的化合物可以以各种剂型使用。为了制成这些剂型，可以适当使用在农业和园艺用灭菌剂的技术领域中目前所使用的各种农药辅助剂。作为农业和园艺用灭菌剂的剂型，例如为乳剂、可湿性粉剂、颗粒可湿性粉剂、水溶剂、液剂、粉剂、胶悬剂、干胶悬剂、细粒剂、粒剂、片剂、油剂、喷雾剂、烟雾剂等。当然，也可以将本发明的化合物1种或组合2种以上而作为有效成分配合。
这种农药辅助剂可以以例如农业和园艺用灭菌剂的效果的提高、稳定化、分散性的提高等目的使用。作为农药辅助剂，可列举例如：载体(稀释剂)、展着剂、乳化剂、湿展剂、分散剂、崩解剂等。作为液体载体，可以列举：水和甲苯、二甲苯等芳香族烃、甲醇、丁醇、乙二醇等醇类、丙酮等酮类、二甲基甲酰胺等酰胺类、二甲基亚砜等亚砜类、甲基萘、环己烷、动植物油、脂肪酸等。另外，作为固体载体，可以使用粘土、高岭土、滑石、硅藻土、二氧化硅、碳酸钙、蒙脱石、膨润土、长石、石英、氧化铝、锯屑、硝基纤维素、淀粉、阿拉伯树胶等。
作为乳化剂和分散剂，可以使用通常的表面活性剂，可以使用例如：高级醇硫酸钠、硬脂基三甲基氯化铵、聚氧乙烯烷基苯基醚、月桂基甜菜碱等阴离子型表面活性剂、阳离子型表面活性剂、非离子型表面活性剂、两性离子型表面活性剂等。另外，可以使用：展着剂；二烷基磺基琥珀酸酯等湿展剂；羧甲基纤维素、聚乙烯醇等固着剂；木质素磺酸钠、月桂基硫酸钠等崩解剂等。
作为农业和园艺用灭菌剂中的有效成分的本发明的化合物的含量，从例如0.01～99.5质量％，优选0.5～90质量％的范围中选择，根据制剂形态、施用方法等各种条件适当确定即可，例如，可以以粉剂中含有约0.5～20质量％左右、优选1～10质量％的有效成分，可湿性粉剂中含有约1～90质量％左右、优选10～80质量％的有效成分，乳剂中含有约1～90质量％左右、优选10～40质量％的有效成分的方式制造。
例如，乳剂的情况下，相对于作为有效成分的本发明的化合物，可以混合溶剂及表面活性剂而制造原液的乳剂，进而，可以在使用该原液时用水稀释至规定浓度而施用。可湿性粉剂的情况下，将作为有效成分的本发明的化合物、固形载体及表面活性剂混合而制造原液，进而，可以在使用该原液时用水稀释至规定浓度而施用。粉剂的情况下，可以将作为有效成分的本发明的化合物、固形载体等混合而直接施用。在粒剂的情况下，可以通过将作为有效成分的本发明的化合物、固形载体及表面活性剂等混合并造粒来制造、直接施用。可是，上述的各制剂形态的制造方法并不限定于上述的方法，本领域技术人员可以根据有效成分的种类和施用目的等适当选择。
在农业和园艺用灭菌剂中，除作为有效成分的本发明的化合物以外，可以配合其它灭菌剂、杀虫剂、杀螨剂、除草剂、植物生长调整剂、肥料、土壤改良剂等任意的有效成分。由本发明的化合物构成的灭菌剂的施用方法没有特别限定，用茎叶散布、土壤处理、设施内的熏烟、熏茎等任一种方法均可以施用。例如，茎叶散布的情况下，可以将例如5～1000ppm、优选10～500ppm的浓度范围的溶液每10公亩以例如50～700升左右的施用量使用。土壤处理的情况下，可以将5～1000ppm的浓度范围的溶液每1m2以0.1～1升左右的施用量使用。
实施例
以下，对本发明进一步使用实施例、制剂例及试验例详细地进行说明，但本发明的范围并不受这些实施例、制剂例及试验例任何限定。
<实施例1>2-氨基烟酸-2-苯氧基苄基的合成
在2-氨基烟酸0.138g的二氯甲烷溶液中加入2-苯氧基己醇0.200g、1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐0.230g和4-二甲基氨基吡啶0.146g，加热回流3小时。冷却至室温后，用二氯甲烷萃取，将水层进一步用二氯甲烷萃取。将有机层合并并且用无水硫酸钠进行干燥。减压下浓缩，将得到的残渣用硅胶柱色谱法精制，由此得到表1中记载的本发明的化合物(编号1)、0.180g、油。此外，同样地操作，合成本发明的化合物。以下的表1中记载与实施例1同样地操作而制造的本发明的化合物。
表1
1)1H-NMR(CDCl3)δppm：4.41(2H，s)、6.55(1H，m)、6.93(3H，m)、7.08(1H，t)、7.18
(1H，t)、7.28-7.35(3H，m)、7.52(1H，d)、7.98(1H，d)、8.19(2H.d)。
2)1H-NMR(CDCl3)δppm：1.63(3H，d)、6.01-6.09(1H，q)、6.62(1H，m)、6.91(1H，d)、
7.03(1H，d)、7.09(1H，s)、7.11-7.18(1H，t)、7.29-7.38(4H，m)、8.19(1H，d)、8.22(1H，d)
3)1H-NMR(CDCl3)δppm：1.64(3H，d)、2.40(3H，s)、6.00-6.06(1H，q)、6.48(1H，d)、
6.92(1H，d)、7.02(1H，d)、7.08(1H，s)、7.09-7.15(1H，t)、7.30-7.38(4H，m)、8.06
(1H，d)
4)1H-NMR(CDCl3)δppm：1.65(3H，d)、6.07(1H，q)、6.62(1H，m)、7.01(4H，m)、7.12
(1H，t)、7.31-7.41(4H，m)、8.21(2H，m)。
5)1H-NMR(CDCl3)δppm：6.47(1H，s)、6.62(1H，m)、7.05-7.11(3H，m)、7.18(1H，t)、
7.22(1H，s)、7.30-7.45(4H，m)、8.12(1H，d)、8.29(1H，d)。
6)1H-NMR(CDCl3)δppm：2.41(3H，s)、5.31(2H，s)、6.48(1H，q)、7.05(4H，m)、
7.44(2H，d)、7.59(2H，d)、8.06(1H，d)
下面示出制剂例。需要说明的是，份表示质量份。
制剂例1乳剂
将本发明的化合物(10份)、二甲苯(60份)、N-甲基-2-吡咯烷酮(20份)及SORPOL 3005X(非离子型表面活性剂和阴离子型表面活性剂的混合物，东邦化学工业株式会社，商品名)(10份)均匀地混合溶解，得到乳剂。
制剂例2可湿性粉剂-1
将本发明的化合物(20份)、NIPSIL NS-K(白炭黑，东曹·二氧化硅株式会社，商品名)(20份)、高岭土粘土(高岭石，竹原化学工业株式会社，商品名)(70份)、サンエキスP-252(木质素磺酸钠，日本制纸化学株式会社，商品名)(5份)及Lennox P65L(烷基烯丙基磺酸盐，东邦化学工业株式会社，商品名)(5份)用空气磨均匀地混合粉碎，得到可湿性粉剂。
制剂例3可湿性粉剂-2
将本发明的化合物(20份)、NIPSIL NS-K(20份)、高岭土粘土(50份)、Lennox 1000C(萘磺酸盐缩合物，东邦化学工业株式会社，商品名)(5份)及SORPOL 5276(非离子型表面活性剂，东邦化学工业株式会社，商品名)(5份)用空气磨均匀地混合粉碎，得到可湿性粉剂。
制剂例4胶悬剂-1
将本发明的化合物(20份)分散于预先混合的丙二醇(5份)、SORPOL7933(阴离子型表面活性剂，东邦化学工业株式会社，商品名)(5份)、水(50份)中，制成浆液状混合物，接着，将该浆液状混合物用戴诺磨(ShinmaruEnterprises社)进行湿式粉碎后，添加预先在水(19.8份)中充分地混合分散有黄原胶(0.2份)的溶液，得到胶悬剂。
制剂例5胶悬剂-2
将本发明的化合物(20份)、ニユ一カルゲンFS-26(二辛基磺基琥珀酸酯和聚氧乙烯三苯乙烯基苯基醚的混合物，竹本油脂株式会社，商品名)(5份)、丙二醇(8份)、水(50份)预先混合，将该浆液状混合物用戴诺磨(Shinmaru Enterprises社)进行湿式粉碎。接着，将黄原胶(0.2份)与水(16.8份)充分地混合分散，制作凝胶状物，与粉碎的浆液充分地混合，得到胶悬剂。
接着，通过试验例显示：本发明的化合物作为灭菌剂的有效成分是有用的。需要说明的是，本发明的化合物用表1中记载的化合物编号表示，用于比较对照的化合物用下述的化合物标记(专利文献1的实施例中记载的化合物)表示。
试验例1：相对于黄瓜灰色霉病的试验
准备播种12天后的黄瓜(品种：相模半白)用于实验。残留该黄瓜的叶轴2cm左右，切取子叶部分。另做如下准备：在32cm×24cm×4.5cm(纵×横×高度)的塑料盒的底部铺设用水充分湿润的纸巾，在纸巾上放置支柱式的网。在该网上以叶子保持水平的方式排列上述的切取的子叶部分。在其子叶的中心部滴加黄瓜灰色霉病菌的胞子悬浮液(1×106个/ml)各50μl。其后，在子叶上覆盖直径6mm的纸盘。另将按照上述制剂例1制备的乳剂进一步用0.02％Tween20脱盐水水溶液稀释，制备规定浓度的稀释液。从纸盘上滴加该稀释液各50μl。在塑料盒上盖上盖子，置于20℃条件下72小时后，测定病斑直径，用下述式求出黄瓜灰色霉病的防除值。将结果示于表1。
防除值(％)＝[1-(处理区病斑直径/无处理区病斑直径)]×100
表2
黄瓜灰色霉病
如上述表2所示，本发明的化合物与化合物A相比，灭菌活性高。
Claims (2)
1.一种2-氨基烟酸酯衍生物，其用下式[I]表示，
式中，R1表示氢原子或C1～C4的烷基，
R2表示氢原子、C1～C4的烷基，或R1和R2相互键合，表示
R3表示氢原子或C1～C4的烷基，
R4表示氢原子、氰基或C1～C4的烷基，
R5及R6相互独立地表示氢原子、卤原子、C1～C4的烷基、C1～C4的烷氧基、C1～C4的烷基硫基、C1～C4的烷基亚硫酰基、C1～C4的烷基磺酰基、硝基、氰基、C1～C4的卤烷基、C1～C4的卤烷氧基或C1～C4的卤烷基硫基，
A及B相互独立地表示次甲基(CH)或氮原子。
2.一种灭菌剂，其特征在于，含有权利要求1所述的2-氨基烟酸酯衍生物作为有效成分。
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| CN111567535A (zh) * | 2020-06-10 | 2020-08-25 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
| CN113966743A (zh) * | 2020-06-10 | 2022-01-25 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
| CN113966743B (zh) * | 2020-06-10 | 2023-07-28 | 青岛海利尔生物科技有限公司 | 一种含琥珀酸脱氢酶抑制剂的杀菌混合物及其应用 |
Also Published As
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| JP6114958B2 (ja) | 2017-04-19 |
| EP2871180A1 (en) | 2015-05-13 |
| EP2871180B1 (en) | 2018-03-21 |
| KR101629767B1 (ko) | 2016-06-13 |
| CA2877235C (en) | 2016-09-20 |
| US9096528B2 (en) | 2015-08-04 |
| AU2013284775A1 (en) | 2015-01-29 |
| HUE037765T2 (hu) | 2018-09-28 |
| ES2665561T3 (es) | 2018-04-26 |
| JPWO2014006945A1 (ja) | 2016-06-02 |
| PL2871180T3 (pl) | 2018-08-31 |
| CN104520273B (zh) | 2016-08-24 |
| MA20150409A1 (fr) | 2015-11-30 |
| ZA201500742B (en) | 2016-09-28 |
| US20150175551A1 (en) | 2015-06-25 |
| MA37825B1 (fr) | 2016-06-30 |
| BR112014032873B1 (pt) | 2019-02-12 |
| CA2877235A1 (en) | 2014-01-09 |
| CO7240428A2 (es) | 2015-04-17 |
| RU2015103515A (ru) | 2016-08-20 |
| UA111542C2 (uk) | 2016-05-10 |
| RU2599725C2 (ru) | 2016-10-10 |
| WO2014006945A1 (ja) | 2014-01-09 |
| AU2013284775B2 (en) | 2015-09-17 |
| EP2871180A4 (en) | 2016-02-24 |
| CL2014003643A1 (es) | 2015-07-31 |
| BR112014032873A2 (pt) | 2017-06-27 |
| KR20150042781A (ko) | 2015-04-21 |
| IN2014DN10806A (zh) | 2015-09-04 |
| PT2871180T (pt) | 2018-05-08 |
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