CN103380123A - 新颖的羧酰胺杀微生物剂 - Google Patents
新颖的羧酰胺杀微生物剂 Download PDFInfo
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- CN103380123A CN103380123A CN2012800097241A CN201280009724A CN103380123A CN 103380123 A CN103380123 A CN 103380123A CN 2012800097241 A CN2012800097241 A CN 2012800097241A CN 201280009724 A CN201280009724 A CN 201280009724A CN 103380123 A CN103380123 A CN 103380123A
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
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Abstract
具有化学式(I)的化合物其中R1是C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基;R2是C1-C4烷基;R3是氢或卤素;R4是氢、C1-C4烷基或C1-C4卤代烷基;X是次甲基或氮;A是R5是氢、卤素、-≡-C1-C6烷基、-≡-C3-C7环烷基或-≡-芳基;R6是氢、卤素、-≡-C1-C6烷基、-≡-C3-C7环烷基或-≡-芳基;以及那些化合物的农用化学上可接受的盐/异构体/结构异构体/立体异构体/非对映异构体/对映异构体/互变异构体以及N-氧化物,这些化合物适合用作杀微生物剂。
Description
本发明涉及新颖的具有杀微生物活性、特别是杀真菌活性的羧酰胺。它进一步涉及在这些化合物的制备中使用的中间体,涉及包括这些化合物的组合物并且涉及它们在农业或园艺中用于控制或预防植物被致植物病微生物(优选真菌)侵染的用途。
例如,在WO2009/016218和WO2010/130767中描述了具有杀真菌活性的N-取代的-N-二环羧酰胺。已经发现,带有特定的取代型式的新颖的羧酰胺具有杀微生物活性。
因此,本发明涉及具有化学式I的N-烷氧基羧酰胺
其中
R1是C1-C4烷基、C1-C4卤代烷基或C1-C4烷氧基;
R2是C1-C4烷基;
R3是氢或卤素;
R4是氢、C1-C4烷基或C1-C4卤代烷基;
X是次甲基或氮;
A是
R5是氢、卤素、-≡-C1-C6烷基、-≡-C3-C7环烷基或-≡-芳基;
R6是氢、卤素、-≡-C1-C6烷基、-≡-C3-C7环烷基或-≡-芳基;
以及那些化合物的农用化学上可接受的盐/异构体/结构异构体/立体异构体/非对映异构体/对映异构体/互变异构体以及N-氧化物。
在取代基的定义中出现的烷基可以是直链或支链的,并且是例如甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、正丁基、仲丁基、异丁基或叔丁基。烷氧基、烯基和炔基衍生自所提及的烷基。卤素通常是氟、氯、溴或碘,优选是氟、溴或氯。这相应地还适用于与其他含义结合的卤素,例如卤代烷基或卤代烷氧基。卤代烷基基团优选地具有一个从1至4个碳原子的链长。卤代烷基是,例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟代乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基;优选是三氯甲基、二氟氯甲基、二氟甲基、三氟甲基、以及二氯氟甲基。烷氧基是,例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基;优选是甲氧基和乙氧基。卤代烷氧基是,例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基和2,2,2-三氯乙氧基;优选是二氟甲氧基、2-氯乙氧基以及三氟甲氧基。环烷基是环丙基、环丁基、环戊基、环己基以及环庚基。
在取代基R5和R6的定义中的芳基优选是苯基、苄基或萘基,或被卤素、氰基、硝基、卤素、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷氨基、C2-C4二烷氨基、C3-C6环烷氨基、C1-C6烷基-C3-C6环烷氨基、C2-C4烷基羰基、C2-C6烷氧基羰基、C2-C6烷氨基羰基、C3-C6二烷氨基羰基、C2-C6烷氧基羰基氧基、C2-C6烷氨基羰基氧基、C3-C6二烷氨基羰基氧基或C3-C6三烷基甲硅烷基单-、二-或三取代的苯基、苄基或萘基。
在优选的具有化学式I的化合物中,彼此独立地,
a)R1是二氟甲基、三氟甲基或甲基;
b)R2是甲基;
c)R3是氢;
d)R4是氢、甲基或乙基;
e)R5是氢或卤素;以及
f)R6是氢或卤素。
在具有化学式I的化合物的一个优选的组中,
R1是二氟甲基或三氟甲基;
R2是甲基;
R3是氢;并且
R4是甲基。
另外的具有化学式I的化合物是优选的,其中
R1是C1-C4卤代烷基;
R2是C1-C4烷基;
R3是氢;
R4是C1-C4烷基;
R5是氢、卤素、-≡-C1-C6烷基或-≡-C3-C7环烷基;
X是次甲基或氮;并且
A是A1。
在具有化学式I的化合物的一个尤其优选的组中,
R1是C1-C4卤代烷基;
R2是C1-C4烷基;
R3是氢;
R4是C1-C4烷基;
R6是氢、卤素、-≡-C1-C6烷基或-≡-C3-C7环烷基;
X是次甲基或氮;并且
A是A2。
具有化学式I的化合物可以通过使具有化学式II的化合物
(其中A是如在式I下所定义的)与具有化学式III的化合物
(其中R1、R2以及R3是如在化学式I下所定义的,并且R*是卤素、羟基或C1-6烷氧基,优选是氯)进行反应来制备。具有化学式III的化合物是已知的并且描述于,例如US5,093,347以及WO2008/148570中或者可以通过本领域已知的方法来制备。例如,具有化学式IIIa的化合物
(其中R9是C1-C6烷基)可以通过使具有化学式IIIb的化合物
(其中R9是如对于化学式IIIa所定义的并且R10是C1-C6烷基)与甲基肼在水、氢氧化物碱以及选自芳烃和卤素取代的芳烃的有机溶剂的存在下进行反应来制备。
有利地在非质子惰性有机溶剂中进行用于具有化学式I的化合物的制备的反应。这样的溶剂是烃,例如苯、甲苯、二甲苯或环己烷,氯化烃,例如二氯甲烷、三氯甲烷、四氯甲烷或氯苯,醚类,例如二乙基醚、乙二醇二甲基醚、二乙二醇二甲基醚、四氢呋喃或二噁烷,腈类,例如乙腈或丙腈,酰胺类,例如N,N-二甲基甲酰胺、二乙基甲酰胺或N-甲基吡咯烷酮。反应温度有利地是在-20℃与+120℃之间。通常,这些反应是轻微放热的并且通常它们可以在环境温度下进行。为了缩短反应时间,或者还有启动该反应,该混合物可以短时间加热到该反应混合物的沸点。反应时间还可以通过添加几滴碱作为反应催化剂而缩短。适合的碱具体是叔胺类,例如三甲胺、三乙胺、奎宁环定、1,4-二氮杂二环[2.2.2]辛烷、1,5-二氮杂二环[4.3.0]壬-5-烯或1,5-二氮杂二环[5.4.0]十一-7-烯。然而,作为碱还可以使用无机碱,例如,氢化物例如氢化钠或氢化钙,氢氧化物例如氢氧化钠或氢氧化钾,碳酸盐例如碳酸钠和碳酸钾,或碳酸氢盐例如碳酸氢钾和碳酸氢钠。这些碱可以按照这样使用或者还可以与催化量的相转移催化剂(例如冠醚,特别是18-冠-6)或一种四烷基铵盐一起使用。
当R*是羟基时,可以使用一种偶联剂,例如苯并***-1-基氧基三(二甲氨基)磷鎓六氟磷酸盐,双-(2-氧代-3-噁唑烷基)-次膦酸酰氯(BOP-Cl),N,N’-二环己基碳二亚胺(DCC)或1,1’-羰基-二咪唑(CDI)。
具有化学式II的中间体
(其中A是如在化学式I下所定义的,优选地,其中R4是C1-C4烷基)是新颖的并且特别地被开发为用于制备具有化学式I的化合物。因此,具有化学式II的这些中间体也形成了本发明的主题的一部分。
对于具有化学式I的化合物的优选的取代基定义也适用于具有化学式II的化合物。
方案1:具有化学式I的化合物(A=A
1
)的合成:
酮1从文献已知并且可以如其中描述地制备(例如Molecules(《分子学》),2009,14,3494-3508)。
方案2:具有化学式I的化合物(A=A
2
)的合成:
酮2的制备描述于文献(Bulletin de la Societé Chimique France(《法国化学学会通报》)1970,1,322-31和Comptes Rendus des Seances de l’Academiedes Sciences,Serie C(C系列):Sciences Chimique(《化学科学》)1968,267(2),156-58)中。使用已知起始材料3-(3-溴丙基)噻吩(Helv.Chim.Acta《瑞士化学》)1995,78(7),1887-93)合成酮2的顺序描述于方案3中。
方案3:酮2的合成:
化合物I以及适当时其互变异构体如果适当的话还能以水合物的形式获得和/或包括其他的溶剂,例如可以用于以固体形式存在的化合物的结晶的那些溶剂。
现在已经发现根据本发明的具有化学式I的化合物具有(用于实用的目的)一个非常有利的针对由致植物病微生物(例如,真菌、细菌或病毒)引起的疾病而保护有用的植物的活性谱。
本发明因此还涉及一种用于控制或预防有用的植物被致植物病微生物侵染的方法,其中将具有化学式I的化合物作为活性成分施用到植物、其部分或其场所。根据本发明的具有化学式I的化合物的区分特色是:在低比率应用下优异的活性、良好地被植物耐受并且是环境安全性的。它们具有非常有用的治疗、预防和***特性,并且用于保护众多有用的植物。具有化学式I的化合物可以被用于抑制或破坏在不同的有用的植物作物的植物或植物部分(果实、花、叶、茎、块茎、根)上发生的疾病,同时还保护了例如随后生长的那些植物部分免受致植物病微生物的影响。
还有可能使用具有化学式I的化合物作为用于处理植物繁殖材料,特别是种子(果实、块茎、籽粒)以及植物插条(例如稻)的种衣剂,用于针对真菌侵染以及针对在土壤中存在的致植物病真菌进行保护。
此外,根据本发明的具有化学式I的化合物可以用于控制有关领域的真菌,例如在工业材料(包括木材以及与木材有关的技术产品)的保护中、在食品贮存中或在卫生管理中。
具有化学式I的化合物例如针对以下类别的致植物病真菌是有效的:半知菌纲(例如葡萄孢属、梨孢属、长蠕孢属、镰刀菌属、壳针孢属(Septoria)、尾孢属和链格孢霉属)和担子菌纲(例如丝核菌属、驼孢锈菌属(Hemileia)、柄锈菌属)。另外,它们还对子囊菌纲(例如黑星菌属和白粉菌属、叉丝单囊壳属(Podosphaera)、链核盘菌属、钩丝壳属)和卵菌纲(例如疫霉属、腐霉属、单轴霉属)有效。已经观察到对白粉病(白粉菌属)的优异活性。此外,新颖的具有化学式I的化合物针对以下项是有效的:致植物病细菌和病毒(例如,针对黄单胞菌属、假单胞菌属、梨火疫病菌以及针对烟草花叶病毒)。已经观察到针对亚洲大豆锈菌病(大豆锈菌)的良好活性。
在本发明的范围内,有待保护的有用的植物典型地包括以下植物种类:谷物(小麦、大麦、黑麦、燕麦、稻、玉米、高粱以及相关种类);甜菜(糖用甜菜以及饲用甜菜);梨果、核果以及无核小水果(苹果、梨、李子、桃、扁桃、樱桃、草莓、覆盆子和黑莓);豆科植物(豆、滨豆、豌豆、大豆);油料作物(油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻油植物、可可豆、落花生);瓜类植物(南瓜、黄瓜、甜瓜);纤维植物(棉花、亚麻、***、黄麻);柑橘属水果(桔、柠檬、葡萄柚、橘);蔬菜(菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯、甜辣椒);樟科(鳄梨、樟属、樟脑)或植物,例如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、藤本植物、啤酒花、香蕉以及天然橡胶植物,连同观赏植物。
术语“有用植物”应当理解为包括由于常规育种方法或基因工程致使其对于除草剂(像溴草腈)或除草剂类(例如像HPPD抑制剂、ALS抑制剂,例如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮-莽草酸-3-磷酸-合成酶(5-enol-pyrovyl-shikimate-3-phosphate-synthase))抑制剂、GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)耐受的有用植物。通过常规的育种(诱变)方法已经致使其对于咪唑啉酮(例如,甲氧咪草烟)耐受的作物的实例是夏季油菜(卡诺拉(Canola))。已经通过基因工程方法致使其对于除草剂或除草剂类耐受的作物的实例包括抗草甘膦和草丁膦的玉米品种,这些品种在 和商标名下是可商购的。
术语“有用植物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的有用的植物,这些毒素如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
这样的植物的实例是:(玉米品种,表达一种CryIA(b)毒素);YieldGard(玉米品种,表达一种CryIIIB(b1)毒素);YieldGard(玉米品种,表达一种CryIA(b)以及一种CryIIIB(b1)毒素);(玉米品种,表达一种Cry9(c)毒素);Herculex(玉米品种,表达一种CryIF(a2)毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达一种CryIA(c)毒素);Bollgard(棉花品种,表达一种CryIA(c)毒素);Bollgard(棉花品种,表达一种CryIA(c)以及一种CryIIA(b)毒素);(棉花品种,表达一种VIP毒素);(马铃薯品种,表达一种CryIIIA毒素);GT Advantage(GA21耐草甘膦性状),CB Advantage(Bt11玉米螟(CB)性状)、RW(玉米根虫性状)以及
术语“有用植物”应当被理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的有用的植物,这些抗病原物质例如所谓的“病程相关蛋白”(PRPs,参见例如EP-A-0392225)。此类抗病原物质以及能够合成此类抗病原物质的转基因植物的实例例如从EP-A-0392225、WO95/33818、和EP-A-0353191是已知的。生产此类转基因植物的方法对于本领域的技术人员通常是已知的并且描述于例如以上提及的公开物中。
如在此使用的,术语“场所”旨在包括这些植物在其上生长的地方,在这些地方这些有用植物的植物繁殖材料被播种或者在这些地方这些植物的植物繁殖材料将被置于土壤中。这样的场所的一个实例是作物植物在其上生长的田地。
术语“植物繁殖材料”应当被理解为表示该植物的生殖部分,如种子,这些部分可以用于该植物的繁殖,以及营养性材料,例如插条或块茎(例如马铃薯)。可以提及,例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或破土后将被移植的发芽植物和幼小植物。这些幼小植物可以在通过浸渍进行完全或部分处理而在移植之前进行保护。优选地,“植物繁殖材料”应当理解为表示种子。
具有化学式I的这些化合物能以未修饰的形式使用,或者优选地与在配制品领域中常规使用的载体与佐剂一起使用。
因此本发明还涉及针对致植物病微生物进行控制和保护的组合物,这些组合物包括具有化学式I的化合物和惰性载体,并且涉及控制或预防有用的植物被致植物病微生物侵染的方法,其中一种组合物,包括作为_umiga成分的具有化学式I的化合物和惰性载体,被施用至这些植物、其部分或其场所。
为此,可以用已知方式将具有化学式I的化合物与惰性载体方便地配制成可乳化的浓缩物、可包衣的糊剂(coatable paste)、直接可喷洒或可稀释的溶液、稀释乳液、可湿性粉剂、可溶性粉剂、尘剂(dust)、颗粒以及还有例如处于聚合物中的胶囊。对于这些组合物的类型,根据预期的目的以及盛行环境来选择施用方法,例如喷洒、雾化、撒粉、播散、包衣或倾倒。这些组合物还可以含有另外的佐剂,如稳定剂、消泡剂、粘度调节剂、粘合剂、增粘剂,以及肥料、微量营养素供体或其他用于获得特殊效果的配制品。
适合的载体和佐剂(助剂)可以是固体或液体并且是在配制品技术中有用的物质,例如天然或再生的矿物质、溶剂、分散剂、湿润剂、增粘剂、增稠剂、粘合剂或肥料。例如在WO97/33890中描述了这样的载体。
可以将具有化学式I的化合物或包括具有化学式I的化合物作为_umiga成分以及一种惰性载体的组合物与另外的化合物同时地或顺序地施用到待处理的植物场所或植物。这些另外的化合物可以是例如肥料或微量营养素供体或其他的影响植物生长的制剂。它们还可以是选择性的除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种这些制剂的混合物,如果希望的话,还有在配制领域通常使用的另外的载体、表面活性剂或促进施用的佐剂。
一种优选的用于施用具有化学式I的化合物、或包括作为_umiga成分的具有化学式I的化合物以及一种惰性载体的组合物的方法是叶施用。施用频率和施用比率将取决于受相应的病原体侵染的风险。然而,具有化学式I的化合物还可以通过用一种液体配制品浸透该植物的场所或者通过将处于固体形式的化合物例如以颗粒的形式(土壤施用)施用到土壤而经由土壤通过根(内吸作用)渗透该植物。在水稻作物中,可以将此种颗粒施用到灌水的稻田中。具有化学式I的化合物还可以通过用一种杀真菌剂的液体配制品浸渍种子或块茎,或通过用一种固体配制品对它们进行包衣而施用到种子(包衣)。
可以用一种已的知方式,典型地通过将该化合物与增充剂,例如溶剂、固体载体以及,任选地,表面活性化合物(表面活性剂)进行精细地混合和/或研磨来制备一种配制品(即,一种包含具有化学式I的化合物,并且如果希望的话,含有一种固体或液体佐剂的组合物)。
这些农用化学配制品将通常含有按重量计从0.1%至99%,优选地按重量计从0.1%至95%的式I的化合物,按重量计99.9%至1%,优选按重量计99.8%至5%的一种固体或液体佐剂以及按重量计从0至25%,优选按重量计从0.1%至25%的一种表面活性剂。
然而优选的是将商业产品配制为浓缩物,最终使用者通常使用稀释的配制品。
有利的施用比率通常是从5g至2kg的活性成分(a.i.)/公顷(ha),优选地从10g至1kg a.i./ha,最优选地从20g至600g a.i./ha。当作为浸种剂使用时,合宜的剂量是从10mg至1g活性物质/kg种子。可以通过实验确定用于所希望的作用的施用比率。它取决于例如作用类型、该有用的植物的发育阶段以及施用(位置、时机、施用方法),并且可以由于这些参数而在宽泛的限值内变化。
以上说明的具有化学式(I)的化合物或其一种药用盐还可以具有有利的针对处理和/或预防动物中的微生物感染的活性谱。“动物”可以是任何动物,例如昆虫、哺乳动物、爬行动物、鱼、两栖动物,优选是哺乳动物,最优选是人类。“处理”表示在具有微生物感染的动物上使用以便降低或减慢或停止该感染的增加或扩散,或降低该感染或治愈该感染。“预防”表示在没有明显的微生物感染迹象的动物上使用以便预防任何将来的感染,或降低或减慢任何将来的侵染的增加或扩散。根据本发明,提供了具有化学式(I)的化合物在制造一种用于处理和/或预防动物中的微生物感染的药物中的用途。还提供了具有化学式(I)的化合物作为一种药用剂的用途。还提供了具有化学式(I)的化合物作为在动物处理中的一种抗微生物剂的用途。根据本发明,还提供了一种药用组合物,该组合物包括作为活性成分的具有化学式(I)的化合物、或其一种药学上可接受的盐、以及一种药学上可接受的_umigate或载体。这种组合物可以用于处理和/或预防动物中的微生物感染。这种药用组合物可以处于一种适合于口服给予的形式,例如片剂、锭剂、硬胶囊、水性悬浮液、油性悬浮液、乳液、可分散粉剂、可分散颗粒、糖浆和酏剂。可替代地,这种药用组合物可以处于一种适合于局部施用的形式,例如一种喷雾剂、乳膏或洗剂。可替代地,这种药用组合物可以处于一种适合于肠胃外给予(例如注射)的形式。可替代地,这种药用组合物可以处于一种可吸入的形式,例如气溶胶喷雾剂。具有化学式(I)的化合物针对不同的能够引起动物中的微生物感染的微生物种类可以是有效的。这样的微生物种类的实例是引起曲霉病的那些,例如Aspergillus_umigate、黄曲霉、土曲霉、构巢曲霉和黑曲霉;引起芽生菌病的那些,例如皮炎芽生菌;引起念珠菌病的那些,例如白色念珠菌、光滑念珠菌、热带念珠菌、***滑念珠菌、克柔念珠菌和葡萄牙念珠菌;引起球孢子菌病的那些,例如粗球孢子菌;引起隐球菌病的那些,例如新生隐球菌;引起组织胞浆菌病的那些,例如荚膜组织胞浆菌;以及引起接合菌病的那些,例如伞枝梨头霉、微小根毛霉和少根根霉。另外的实例是镰刀菌属,例如尖孢镰刀菌和茄病镰刀菌,以及足放线病菌属,例如尖端赛多孢子菌和多育赛多孢子菌。仍另外的实例是小孢子菌属、发癣菌属、表皮癣菌属、毛霉属、孢子丝菌属、瓶霉属、枝孢霉属、霉样真霉属、副球孢子菌属和组织胞浆菌属。
以下非限制性的实例更详细地展示了以上描述的发明而非对其进行限制。
制备实例:
实例1:3-二氟甲基-1-甲基-1H-吡唑-4-羧酸甲氧基-(5,6,7,8-四氢-4H-环庚并[b]
噻吩-8-基)酰胺(化合物编号2.35)的制备:
步骤1:在环境温度下,将由1.67g(10.05mmol)的4,5,6,7-四氢-环庚并[b]噻吩-8-酮、1.05g(12.56mmol)的O-甲基羟胺盐酸盐、0.99g(12.56mmol)的吡啶以及37ml的甲醇组成的混合物在一个磺化烧瓶中搅拌20小时。将所得溶液用500ml的乙酸乙酯进行稀释并且将有机相用水洗涤3次。在将有机相用硫酸钠进行干燥并且在水喷射真空中将溶剂馏出以后,获得了粗反应产物。将原料通过硅胶快速层析法(洗脱液乙酸乙酯/庚烷1:6)进行纯化,获得了1.96g的(4,5,6,7-四氢环庚并[b]噻吩-8-酮)-O-甲基肟(淡黄色油)。
步骤2:在一个磺化烧瓶中,将从步骤1获得的1.92g(9.84mmol)的O-甲基肟溶解于30ml的乙酸中。在大约1.5小时的时间内分部分地添加1.24g(19.68mmol)的NaCNBH3。搅拌18小时之后,另外添加309mg的NaCNBH3并且继续搅拌42小时。将所得溶液用50ml的水进行稀释并且通过添加120ml的4N NaOH水溶液将pH调节至8。将水相用AcOEt萃取3次。将有机相用硫酸钠进行干燥并且在水喷射真空中将溶剂馏出。将粗制油状物通过硅胶快速层析法(洗脱液:TBME/庚烷1:6)进行纯化。获得了1.28g的处于无色液体形式的O-甲基-N-(5,6,7,8-四氢-4H-环庚并[b]噻吩-8-基)羟胺。
步骤3:在一个磺化烧瓶中,将在步骤2中获得的0.62g(3.15mmol)的O-甲基羟胺溶解于30ml的二氯甲烷和0.48g(4.7mmol)的三乙胺中并且在大约10分钟内缓慢添加0.74g(3.78mmol)3-二氟甲基-1-甲基-1H-吡唑-4羧酸氯化物和10ml的混合物。将该反应混合物在环境温度下搅拌16小时。将该溶剂部份地馏出并且将该残余物通过硅胶快速层析法(洗脱液:乙酸乙酯/庚烷1:1)直接进行纯化。获得0.93g的、呈白色粉末的化合物2.35(m.p.:130℃-132℃)。
实例2:3-二氟甲基-1-甲基-1-H-吡唑-4-羧酸(2-溴-5,6,7,8-四氢-4H-环庚并[b]噻
吩-8-基)甲氧基酰胺(化合物编号2.41)的制备:
在一个磺化烧瓶中,将213mg(0.6mmol)的化合物2.35、214mg(1.2mmol)N-溴代琥珀酰亚胺(NBS)以及5ml的纯吡啶在75℃(浴温度)搅拌8小时。将所得混合物用50ml的AcOEt进行稀释并且然后用10ml的水洗涤3次。将有机相用硫酸钠进行干燥并且在水喷射真空中将溶剂去除。将所得粗材料通过硅胶快速层析法(洗脱液:乙酸乙酯/庚烷1:1)进行纯化。获得237mg的处于浅棕色粉末形式的化合物2.41(m.p.:124℃-126℃)。
实例3:3-二氟甲基-1-甲基-1H-吡唑-4-羧酸[2-(3,3-二甲基丁-1-炔基)-5,6,7,8-
四氢-4H-环庚并[b]噻吩-8-基]甲氧基酰胺(化合物2.47):
在一个磺化烧瓶中,将218mg(0.5mmol)的化合物2.41、124mg(1.5mmol)3,3-二甲基-1-丁炔、8.7mg Cu(I)I(0.046mmol)、32mg(0.046mmol)的双-(三苯基膦)-二氯化钯以及30ml的三乙胺的混合物在70℃搅拌16小时。然后将三乙胺馏出并且将该残余物通过硅胶快速层析法(洗脱液:乙酸乙酯/庚烷1:2)进行纯化。获得160mg的处于浅棕色粉末形式的化合物2.47(m.p.:114℃-116℃)。
表1:具有化学式I的化合物,其中A是A
1
:(“Me”表示甲基)
表2:具有化学式I的化合物,其中A是A
2
:
表3:表征数据:
表3显示了对于表1至表2的化合物的选择的熔点以及选择的NMR数据。除非另外说明,将CDCl3用作用于NMR测量的溶剂。如果存在溶剂的混合物,这被表示为,例如:CDCl3/d6-DMSO)。没有作出在所有情况下列出所有表征数据的尝试。
在表3以及随后的整个说明书中,以摄氏度的形式给出温度;“NMR”表示核磁共振谱;MS表示质谱;“%”是重量百分数,除非以其他单位指示相应的浓度。整个本说明书使用了以下缩写:
m.p.=熔点 b.p.=沸点
S= 单峰 br= 宽峰
d= 二重峰 dd= 双二重峰
t= 三重峰 q= 四重峰
m= 多重峰 ppm= 百万分率
用于GC-MS的方法
挥发性CI/EI
在一台Thermo MS:DSQ和GC:TRACE GC ULTRA上利用来自Zebronphenomenex的柱进行GC-MS来获得质谱:相ZB-5ms15m,直径:0.25mm,0.25μm,H2流速1.7mL/min,进样器温度:250℃,检测器温度:220℃,方法:保持在40℃2分钟,25℃/min直到320℃,在320℃保持1分12秒,总时间15分钟。除非另外说明,所有其他的试剂和溶剂购自商业上的供应商并且使用时无需进一步纯化。
用于LC-MS的方法
方法C
表3:
具有化学式I的化合物的配制品实例:
实例F-1.1至F-1.2:可乳化的浓缩物
可以通过用水稀释这样的浓缩物来制备任何希望浓度的乳液。
实例F-2:可乳化的浓缩物
可以通过用水稀释这样的浓缩物来制备任何希望浓度的乳液。
实例F-3.1至F-3.4:溶液
这些溶液适合于以微滴的形式使用。
实例F-4.1至F-4.4:颗粒剂
将该新颖的化合物溶解在二氯甲烷中,将溶液喷洒到载体上,并且然后通过在真空下蒸馏除去溶剂。
实例F-5.1和F-5.2:尘剂
通过精细混合所有组分获得即用型尘剂。
实例F-6.1至F-6.3:可湿性粉剂
混合所有组分,并且在适合的研磨机中充分研磨该混合物以给出可湿性粉剂,可以用水将其稀释为具有任何希望的浓度的悬浮液。
实例F7:用于种子处理的可流动浓缩物
将这种精细研磨的活性成分与这些佐剂充分混合,从而给出一种悬浮液浓缩物,通过用水稀释可以从该浓缩物获得任何所希望的稀释度的悬浮液。使用这样的稀释物,可以通过喷洒、倾倒或浸渍对活的植物连同植物繁殖材料进行处理并且保护它们免受微生物侵染。
生物学实例:杀真菌作用:
实例B-1:针对葡萄生单轴霉/葡萄/叶圆片预防性(晚疫病)的作用:将葡萄藤叶圆片置于多孔板(24孔规格)中的水琼脂上并且用测试溶液进行喷洒(200ppm活性成分)。在干燥之后,将叶圆片用真菌的孢子悬浮液接种。在适当的孵育之后,化合物的活性在7dpi(接种之后的天数)被评定为预防性杀真菌活性。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.2和1.5显示出良好活性(≥50%抑制)。
实例B-2:小麦白粉病菌(Blumeria graminis f.sp.tritici,Erysiphe graminis f.
sp.tritici)/小麦/叶圆片预防性(小麦上的白粉病):
将小麦叶节置于多孔板(24孔规格)中的琼脂上并且用测试溶液进行喷洒(200ppm活性成分)。在干燥之后,将叶圆片用真菌的孢子悬浮液接种。在适当的孵育之后,化合物的活性在4dpi(接种之后的天数)被评定为预防性杀真菌活性。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.5以及1.35显示出非常好的活性(≥70%抑制)。
实例B-3:小麦叶锈菌/小麦/叶圆片预防性(褐锈病):
将小麦叶节置于多孔板(24孔规格)中的琼脂上并且用测试溶液进行喷洒(200ppm活性成分)。在干燥之后,将叶圆片用真菌的孢子悬浮液接种。在适当的孵育之后,化合物的活性在8dpi(接种之后的天数)被评定为预防性杀真菌活性。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40、2.41以及2.47显示出非常好的活性(≥80%抑制)。
实例B-4:小麦叶锈菌/小麦/叶圆片治疗性(褐锈病):
将小麦叶节置于多孔板(24孔规格)内的琼脂上。然后用真菌的孢子悬液接种这些叶圆片。接种一天之后,施用测试溶液(200ppm活性成分)。在适当的孵育之后,化合物的活性在8dpi(接种之后的天数)被评定为治疗性杀真菌活性。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40、2.41以及2.47显示出非常好的活性(≥80%抑制)。
实例B-5:圆核腔菌/大麦/叶圆片预防性(网斑病):
将大麦叶节置于多孔板(24孔规格)中的琼脂上并且用测试溶液进行喷洒(200ppm活性成分)。在干燥之后,将叶圆片用真菌的孢子悬浮液接种。在适当的孵育之后,化合物的活性在4dpi(接种之后的天数)被评定为预防性杀真菌活性。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40以及2.41显示出非常好的活性(≥80%抑制)。
实例B-6:灰葡萄孢菌(Botryotinia fuckelian,Botrytis cinerea)/液体培养
(灰霉病):
将来自冷冻储存的真菌分生孢子直接混入营养肉汤中。在将测试化合物(200ppm活性成分)的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且在3-4天之后通过光度法确定对生长的抑制。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40以及2.41显示出非常好的活性(≥80%抑制)。
实例B-7:落花生球腔菌(落花生尾孢(Cercospora arachidicola))/液体培
养(早期叶斑病):
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物(200ppm活性成分)的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且在6-7天之后通过光度法测量对生长的抑制。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40、2.41以及2.47显示出非常好的活性(≥80%抑制)。
实例B-8:禾生球腔菌(小麦壳针孢)/液体培养(叶枯病(Septoria
blotch)):
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物(200ppm活性成分)的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且在4天之后通过光度法测量对生长的抑制。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40、2.41以及2.47显示出非常好的活性(≥80%抑制)。
实例B-9:水稻纹枯病菌(立枯丝核菌)/液体培养(根腐病,猝倒病):
将新培养的真菌液体培养物的菌丝体片段直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中以后,添加含有真菌材料的营养肉汤。将这些测试板在24℃进行孵育并且施用之后3-4天通过光度法确定对生长的抑制。化合物的活性被表示为真菌生长抑制(0=没有生长抑制,80%至99%的等级表示好到非常好的抑制,100%=完全抑制)。在这个测试中,化合物编号1.1、1.2、1.4、1.5、1.35、1.37、1.40、1.41、2.34、2.37、2.38、2.40以及2.41显示出非常好的活性(≥80%抑制)。
Claims (7)
2.根据权利要求1所述的具有化学式I的化合物,其中
R1是二氟甲基或三氟甲基;
R2是甲基;
R3是氢;并且
R4是甲基。
3.根据权利要求1所述的具有化学式I的化合物,其中
R1是C1-C4卤代烷基;
R2是C1-C4烷基;
R3是氢;
R4是C1-C4烷基;
R5是氢、卤素、-≡-C1-C6烷基或-≡-C3-C7环烷基;
X是次甲基或氮;并且
A是A1。
4.根据权利要求1所述的具有化学式I的化合物,其中
R1是C1-C4卤代烷基;
R2是C1-C4烷基;
R3是氢;
R4是C1-C4烷基;
R6是氢、卤素、-≡-C1-C6烷基或-≡-C3-C7环烷基;
X是次甲基或氮;并且
A是A2。
6.一种用于控制或预防有用的植物被致植物病微生物侵染的方法,其中将根据权利要求1所述的具有化学式I的化合物或包括这种化合物作为活性成分的一种组合物施用至这些植物、其部分或其场所。
7.一种用于控制致植物病微生物并且针对其进行保护的组合物,包括根据权利要求1所述的具有化学式I的化合物和至少一种助剂。
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PCT/EP2012/052644 WO2012113696A1 (en) | 2011-02-21 | 2012-02-16 | Novel carboxamide microbiocides |
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US (1) | US8822523B2 (zh) |
EP (1) | EP2678328B1 (zh) |
CN (1) | CN103380123B (zh) |
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US8552049B2 (en) * | 2010-05-28 | 2013-10-08 | Syngenta Corp Protection, LLC | Pyrazolecarboxamide derivatives and their use as microbiocides |
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EP1792901A1 (en) * | 2005-11-22 | 2007-06-06 | Bayer CropScience S.A. | N-(1-alkyl-2-phenylethyl)-carboxamide derivatives and use thereof as fungicides |
CN101765589A (zh) * | 2007-07-31 | 2010-06-30 | 拜尔农科股份有限公司 | 杀真菌剂n-环烷基-n-双环-羧酰胺衍生物 |
WO2010130767A2 (en) * | 2009-05-15 | 2010-11-18 | Bayer Cropscience Ag | Fungicide pyrazole carboxamides derivatives |
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CA1340685C (en) | 1988-07-29 | 1999-07-27 | Frederick Meins | Dna sequences encoding polypeptides having beta-1,3-glucanase activity |
ES2199931T3 (es) | 1989-03-24 | 2004-03-01 | Syngenta Participations Ag | Plantas transgenicas resistentes a enfermedades. |
US5639949A (en) | 1990-08-20 | 1997-06-17 | Ciba-Geigy Corporation | Genes for the synthesis of antipathogenic substances |
US5093347A (en) | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
US6262058B1 (en) | 1996-03-11 | 2001-07-17 | Syngenta Crop Protection, Inc. | Pyrimidin-4-one derivatives as pesticide |
CL2008001647A1 (es) | 2007-06-08 | 2008-10-10 | Syngenta Participations Ag | Compuestos derivados de feniletil-amida de acido-1h-pirazol-4-carboxilico; compuestos derivados de (feniletil)amina; metodo para controlar o prevenir la infestacion de plantas por parte de microorganismos fitopatogenos; y composicion para el control |
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2012
- 2012-02-16 BR BR112013021121-0A patent/BR112013021121B1/pt not_active IP Right Cessation
- 2012-02-16 US US14/000,486 patent/US8822523B2/en active Active
- 2012-02-16 WO PCT/EP2012/052644 patent/WO2012113696A1/en active Application Filing
- 2012-02-16 CN CN201280009724.1A patent/CN103380123B/zh not_active Expired - Fee Related
- 2012-02-16 ES ES12703835.4T patent/ES2532715T3/es active Active
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EP1792901A1 (en) * | 2005-11-22 | 2007-06-06 | Bayer CropScience S.A. | N-(1-alkyl-2-phenylethyl)-carboxamide derivatives and use thereof as fungicides |
CN101765589A (zh) * | 2007-07-31 | 2010-06-30 | 拜尔农科股份有限公司 | 杀真菌剂n-环烷基-n-双环-羧酰胺衍生物 |
WO2010130767A2 (en) * | 2009-05-15 | 2010-11-18 | Bayer Cropscience Ag | Fungicide pyrazole carboxamides derivatives |
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CN109541092A (zh) * | 2018-12-07 | 2019-03-29 | 江苏省农业科学院 | 一种大蒜白腐菌粗毒素鉴定方法 |
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US8822523B2 (en) | 2014-09-02 |
CN103380123B (zh) | 2015-05-20 |
BR112013021121A2 (pt) | 2016-07-19 |
US20140031405A1 (en) | 2014-01-30 |
ES2532715T3 (es) | 2015-03-31 |
BR112013021121B1 (pt) | 2019-05-14 |
WO2012113696A1 (en) | 2012-08-30 |
EP2678328B1 (en) | 2015-01-21 |
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