CN101479260B - 唑基甲基环氧乙烷及其在防治植物病原性真菌中的用途和包含它们的组合物 - Google Patents
唑基甲基环氧乙烷及其在防治植物病原性真菌中的用途和包含它们的组合物 Download PDFInfo
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- CN101479260B CN101479260B CN200780023501XA CN200780023501A CN101479260B CN 101479260 B CN101479260 B CN 101479260B CN 200780023501X A CN200780023501X A CN 200780023501XA CN 200780023501 A CN200780023501 A CN 200780023501A CN 101479260 B CN101479260 B CN 101479260B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Abstract
本发明涉及通式I的唑基甲基环氧乙烷及其植物相容性酸加成盐或金属盐:其中:A为被三个F取代的苯基,B为未取代的吡啶基、噻吩基、噻唑基、噁唑基或呋喃基或被1-3个如下取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、巯基或C1-C4烷硫基,本发明还涉及式I化合物在防治植物病原性真菌中的用途以及包含这些化合物的组合物。
Description
本发明涉及通式I的唑基甲基环氧乙烷及其植物相容性酸加成盐或金属盐:
其中:
A为被三个F取代的苯基,
B为未取代的吡啶基、噻吩基、噻唑基、噁唑基或呋喃基或被1-3个如下取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、巯基或C1-C4烷硫基。
此外,本发明还涉及式I化合物在防治植物病原性真菌中的用途以及包含这些化合物的组合物。
唑基甲基环氧乙烷、它们的制备和在作物保护中的用途例如由EP-A 0094 564和EP-A 0 196 038已知。
在环氧乙烷环上带有杂芳基取代基的唑基甲基环氧乙烷由EP-A 0 421125已知。
尽管已经描述的唑基甲基环氧乙烷对许多病原体具有良好至非常良好的杀真菌活性,本发明的目的是提供具有改进的杀真菌活性的新的唑基甲基环氧乙烷。
该目的由开头所述的式I化合物实现。
由于它们的氮原子的碱性性质,化合物I能够与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例为氢卤酸,如氢氟酸、盐酸、氢溴酸和氢碘酸,碳酸, 硫酸,磷酸和硝酸。
合适的有机酸例如为甲酸和链烷酸如乙酸,三氟乙酸,三氯乙酸和丙酸,以及乙醇酸,硫氰酸,乳酸,琥珀酸,柠檬酸,苯甲酸,肉桂酸,草酸,烷基磺酸(具有1-20个碳原子的直链或支化烷基的磺酸),芳基磺酸或芳基二磺酸(带有1或2个磺酸基团的芳族基团如苯基和萘基),烷基膦酸(具有1-20个碳原子的直链或支化烷基的膦酸),芳基膦酸或芳基二膦酸(带有1或2个磷酸基团的芳族基团如苯基和萘基),其中烷基或芳基可进一步带有其它取代基,如对甲苯磺酸,水杨酸,对氨基水杨酸,2-苯氧基苯甲酸,2-乙酰氧基苯甲酸等。
合适的金属离子尤其为第二主族元素,尤其是钙和镁,第三和第四主族,尤其是铝、锡和铅,以及第1-8过渡族元素,尤其是铬、锰、铁、钴、镍、铜、锌的离子和其它离子。特别优选第四周期过渡族的元素的金属离子。金属离子可以它们可采用的各种价态存在。
式I化合物的制备是已知的且详细描述于EP-A 0 094 564、EP-A 0 196038和EP-A 0 421 125中。
在上式所给符号的定义中,使用通常代表如下取代基的集合性术语:
卤素:氟、氯、溴和碘;
烷基和复合基团如烷基氨基中的烷基结构部分:如优选具有1-4个碳原子的饱和直链或支化烃基如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基和1,1-二甲基乙基。
卤代烷基:如上所定义的烷基,其中这些基团中的一些或所有氢原子被上述卤原子替换。在一个实施方案中,烷基被特定卤原子,优选氟、氯或溴取代至少1次或完全取代。在另一实施方案中,烷基被不同的卤原子部分或完全卤代;在混合卤素取代的情况下,优选氯和氟的组合。特别优选(C1-C4)卤代烷基,更优选(C1-C2)卤代烷基,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、五氟乙基或1,1,1-三氟丙-2-基;
烷氧基:经由氧连接的如上所定义的烷基,其优选具有1-4个碳原子。优选烷氧基的实例为: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。
卤代烷氧基:如上所定义的烷氧基,其中这些基团中的一些或所有氢原子被如上在卤代烷基下所定义的卤原子,尤其是氟、氯或溴替换。优选卤代烷氧基的实例为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-(CH2F)-2-氟乙氧基、1-(CH2Cl)-2-氯乙氧基、1-(CH2Br)-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基或九氟丁氧基。
烷硫基:经由硫原子连接的如上所定义的烷基。
式I的新化合物包含手性中心且通常以外消旋体形式或以赤式和苏式的非对映体混合物得到。本发明化合物的赤式和苏式的非对映体可被分离并以纯净形式分离,例如基于它们的不同溶解度或通过柱色谱分离。使用已知方法,如均匀的非对映体对可用于得到均匀的对映体。适合用作杀菌剂的是均匀的非对映体或对映体和在合成中得到的其混合物。这相应适用于杀真菌组合物。此处优选对映体对或环B和三唑基甲基取代基顺式排列的对映体。
本发明化合物可以各种晶型存在,这些晶型的生物活性可能不同。它们也由本发明提供。
在本发明的式I化合物中或在根据本发明使用的式I化合物中,特别优选如下取代基含义,在每种情况下单独或组合。此处,合适的话,优选取代基或优选的取代基组合相应适用于本发明化合物的前体。
取代基A为被三个F取代的苯基,从而得到总共6个下式的取代基A1-A6:
根据一个实施方案,A为A1、A2、A3或A4。
根据另一实施方案,A为A1或A2。
根据优选实施方案,A为A1。
根据另一实施方案,A为A2。
根据另一实施方案,A为A3。
根据另一实施方案,A为A4。
根据另一实施方案,A为A5或A6。
根据另一实施方案,A为A5。
根据另一实施方案,A为A6。
另一实施方案涉及其中B为未取代吡啶基、噻吩基、噻唑基、噁唑基或呋喃基的化合物I。
根据优选实施方案,B为吡啶基或噻吩基。
根据另一优选实施方案,B为吡啶基。
在本发明的另一实施方案中,B为被1-3个如下取代基取代的苯基:卤素、NO2、氨基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷基氨基、C1-C4二烷基氨基、巯基或C1-C4烷硫基。
在另一实施方案中,B为被1-3个如下取代基取代的苯基:卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基。
在优选实施方案中,B为被1-3个卤素取代的苯基。
尤其是对于它们的用途,优选汇集在下表2-7中的本发明化合物I。此外,对表中取代基提及的基团本身为所述取代基的特别优选实施方案,而与其中提及它们的组合无关。
表1
行 | 取代基B |
1-1 | 2-甲基苯基 |
1-2 | 3-甲基苯基 |
1-3 | 4-甲基苯基 |
1-4 | 2-甲氧基苯基 |
1-5 | 3-甲氧基苯基 |
1-6 | 4-甲氧基苯基 |
1-7 | 2-氯苯基 |
1-8 | 3-氯苯基 |
1-9 | 4-氯苯基 |
1-10 | 2-氟苯基 |
1-11 | 3-氟苯基 |
1-12 | 4-氟苯基 |
1-13 | 2-氯-3-甲氧基苯基 |
1-14 | 2-氯-4-甲氧基苯基 |
1-15 | 2,3-二氯苯基 |
1-16 | 2,4-二氯苯基 |
1-17 | 3,4-二氯苯基 |
1-18 | 2,3-二氟苯基 |
1-19 | 2,4-二氟苯基 |
1-20 | 2-氯-3-氟苯基 |
1-21 | 2-氯-4-氟苯基 |
1-22 | 2-吡啶基 |
1-23 | 3-吡啶基 |
1-24 | 4-吡啶基 |
1-25 | 2-噻吩基 |
1-26 | 3-噻吩基 |
1-27 | 噻唑-4-基 |
1-28 | 噻唑-5-基 |
行 | 取代基B |
1-29 | 噁唑-4-基 |
1-30 | 噁唑-5-基 |
1-31 | 2-呋喃基 |
表2
其中A为A1且B在每种情况下对应于表1的一行的取代基的式I化合物。
表3
其中A为A2且B在每种情况下对应于表1的一行的取代基的式I化合物。
表4
其中A为A3且B在每种情况下对应于表1的一行的取代基的式I化合物。
表5
其中A为A4且B在每种情况下对应于表1的一行的取代基的式I化合物。
表6
其中A为A5且B在每种情况下对应于表1的一行的取代基的式I化合物。
表7
其中A为A6且B在每种情况下对应于表1的一行的取代基的式I化合物。
化合物I适合作为杀真菌剂。它们对选自子囊菌纲(Ascomycetes)、半知菌纲(Deuteromycetes)、卵菌纲(Oomycetes)和担子菌纲(Basidiomycetes)的宽范围植物病原性真菌,尤其是对于选自卵菌纲的植物病原性真菌具有优异的活性。它们中的一些内吸有效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。
它们对在各种作物植物如小麦、黑麦、大麦、燕麦、稻、玉米、禾草、香蕉、棉花、大豆、咖啡、甘蔗、葡萄藤、水果和观赏植物以及蔬菜植物如黄瓜、豆类、西红柿、土豆和葫芦科植物以及这些植物的种子中防治大 量真菌尤其重要。
它们尤其适合防治下列植物病害:
·蔬菜、油籽油菜、糖用甜菜、水果和稻上的链格孢属(Alternaria),例如土豆和西红柿上的早疫链格孢(A.solani)或链格孢(A.alternata);
·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);
·玉米、禾谷类、稻和草坪中的平脐蠕孢属(Bipolaris)和内脐蠕孢属(Drechslera),例如玉米上的玉蜀黍平脐蠕孢(D.maydis);
·禾谷类上的禾白粉菌(Blumeria graminis)(白粉病);
·草莓、蔬菜、花卉和葡萄藤上的灰葡萄孢(Botrytis cinerea)(灰霉病),
·莴苣上的莴苣盘梗霉(Bremia lactucae),
·玉米、大豆、稻和糖用甜菜上的尾孢属(Cercospora);
·玉米、禾谷类、稻上的旋孢腔菌属(Cochliobolus),例如禾谷类上的禾旋孢腔菌(Cochliobolus sativus),稻上的宫部旋孢腔菌(Cochliobolusmiyabeanus);
·大豆和棉花上的剌盘孢属(Colletotricum);
·玉米、禾谷类、稻和草坪上的内脐蠕孢属(Drechslera)、核腔菌属(Pyrenophora),例如大麦上的大麦网斑内脐蠕孢(D.teres)或小麦上的D.tritci-repentis;
·由Phaeoacremonium chlamydosporium、Ph.Aleophilum和Formitipora punctata(同义词斑孔木层孔菌(Phellinus punctatus))引起的葡萄藤上的埃斯卡(Esca);
·玉米上的突脐蠕孢属(Exserohilum),
·黄瓜植物上的二孢白粉菌(Erysiphe cichoracearum)和单丝壳白粉菌(Sphaerotheca fuliginea),
·各种植物上的镰孢霉属(Fusarium)和轮枝孢属(Verticillium),例如禾谷类上的禾本科镰孢(F.graminearum)或大刀镰孢(F.culmorum)或多种植物如西红柿上的尖镰孢(F.oxysporum);
·禾谷类上的禾顶囊壳(Gaeumanomyces graminis);
·禾谷类和稻上的赤霉属(Gibberella)(例如稻上的藤仓赤霉(Gibberellafujikuroi));
·稻上的Grainstaining complex;
·玉米和稻上的长蠕孢属(Helminthosporium);
·禾谷类上的Michrodochium nivale;
·禾谷类、香蕉和花生上的球腔菌属(Mycosphaerella),例如小麦上的禾生球腔菌(M.graminicola)或香蕉上的斐济球腔菌(M.fijiensis);
·卷心菜和球茎植物上的霜霉属(Peronospora),例如卷心菜上的芸苔霜霉(P.brassicae)或洋葱上的大葱霜霉(P.destructor);
·大豆上的豆薯层锈菌(Phakopsora pachyrhizi)和山马蟥层锈菌(Phakopsara meibomiae);
·大豆和向日葵上的拟茎点霉属(Phomopsis);
·土豆和西红柿上的致病疫霉(Phytophthora infestans);
·各种植物上的疫霉属(Phytophthora),例如柿子椒上的辣椒疫霉(P.capsici);
·葡萄藤上的葡萄生单轴霉(Plasmopara viticola),
·苹果上的苹果白粉病菌(Podosphaera leucotricha),
·禾谷类上的小麦基腐病菌(Pseudocercosporella herpotrichoides),
·各种植物上的假霜霉属(Pseudoperonospora),例如黄瓜上的古巴假霜霉(P.Cubensis)或啤酒花上的葎草假霜(P.Humili);
·各种植物上的柄锈菌属(Puccinia),例如禾谷类上的小麦柄锈菌(P.triticina)、条形柄锈病(P.striformis)、大麦柄锈病(P.hordei)或禾柄锈菌(P.graminis),或芦笋上的天门冬属柄锈病(P.asparagi));
·稻上的稻瘟病菌(Pyricularia oryzae)、笹木伏革菌(Corticium sasakii)、帚梗柱孢属(Sarocladium oryzae)、稻叶鞘腐败病(S.attenuatum)、稻叶黑粉菌(Entyloma oryzae),
·草坪和禾谷类上的稻梨孢菌(Pyricularia grisea),
·草坪、稻、玉米、棉花、油籽油菜、向日葵、糖用甜菜、蔬菜和其他植物上的腐霉属(Pythium),例如各种植物上的终极腐霉菌(P.ultiumum), 草坪上的瓜果腐霉(P.aphanidermatum);
·棉花、稻、土豆、草坪、玉米、油籽油菜、糖用甜菜、蔬菜和各种植物上的丝核菌属(Rhizoctonia),例如甜菜和各种植物上的立枯丝核病菌(R.solani);
·大麦、黑麦和黑小麦上的黑麦喙孢(Rhynchosporium secalis);
·油籽油菜和向日葵上的核盘菌属(Sclerotinia);
·小麦上的小麦壳针孢(Septoria tritici)和颖枯壳多孢(Stagonosporanodorum),
·葡萄藤上的葡萄钩丝壳(Erysiphe(同义词Uncinula)necator),
·玉米和草坪上的Setospaeria属,
·玉米上的丝轴黑粉菌(Sphacelotheca reilinia),
·大豆和棉花上的根串珠霉属(Thievaliopsis),
·禾谷类上的腥黑粉菌属(Tilletia),
·禾谷类、玉米和甘蔗上的黑粉菌属(Ustilago),例如玉米上的玉蜀黍黑粉菌(U.maydis);
·苹果和梨上的黑星菌属(Venturia)(黑星病),例如苹果上的苹果黑星病(V.inaequalis)。
它们特别适合防治选自Peronosporomycetes(同义词:卵菌纲)的有害真菌如霜霉属、疫霉属、葡萄生单轴霉、假霜霉属和腐霉属。
化合物I还适于防治有害真菌以保护材料(如木材、纸张、漆分散体、纤维或织物)和保护储藏的产品。在木材保护中,特别应注意下列有害真菌:子囊菌纲真菌,如线嘴壳属(Ophiostoma spp.),长喙壳属(Ceratocystisspp.),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,如粉孢革菌属(Coniophoraspp.),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(Serpula spp.)和干酪菌属(Tyromyces spp.),半知菌纲真菌,如曲霉属(Aspergillus spp.),枝孢属(Cladosporium spp.),青霉属(Penicillium spp.), 木霉属(Trichoderma spp.),链格孢属(Alternaria spp.),拟青霉属(Paecilomyces spp.)和接合菌纲(Zygomycetes)真菌,如毛霉属(Mucor spp.),此外在材料保护中应注意下列酵母:假丝酵母属(Candida spp.)和酿酒酵母(Saccharomyces cerevisae)。
化合物I通过用杀真菌有效量的活性化合物处理真菌或需要防止真菌侵袭的植物、种子或材料或者土壤而使用。施用可以在材料、植物或种子被真菌侵染之前和之后进行。
杀真菌组合物通常包含0.1-95重量%,优选0.5-90重量%活性化合物。
当用于作物保护时,施用率取决于所需效果的种类为0.01-2.0kg活性化合物/公顷。
在种子处理中,活性化合物的所需量通常为1-1000g/100kg种子,优选5-100g/100kg种子。
当用于保护材料或储存的产品时,活性化合物的施用率取决于施用区域的种类和所需效果。在材料保护中典型的施用量例如为每立方米处理材料0.001g-2kg,优选0.005g-1kg活性化合物。
式I化合物可以生物活性可能不同的各种晶型存在。它们同样为本发明主题。
可以将化合物I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的目的;在每种情况下应确保本发明化合物精细和均匀地分布。
配制剂以本身已知的方式制备,例如通过将活性化合物与溶剂和/或载体混合而制备,需要的话使用乳化剂和分散剂。适合于此的溶剂/助剂主要为:
-水、芳族溶剂(如 产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如细碎的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂 肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
适合用作表面活性剂的是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘和萘衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基酚、辛基酚、壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾溶液、乳液、糊或油分散体的是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、环己醇、环己酮、异佛尔酮,强极性溶剂,例如二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、浸渍颗粒和均质颗粒可以通过将活性化合物与固体载体粘附而制备。固体载体的实例是矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁;磨碎的合成材料;肥料如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。活性化合物以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.用水稀释的产品
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。得到活性化合物含量为10重量%的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。
C)乳油(EC)
将15重量份活性化合物溶于75重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D)乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(如Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中的活性化合物含量为20重量%。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(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化合物分散体或溶液。该配制剂的活性化合物含量为50重量%。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散 剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
H)凝胶配制剂(GF)
在球磨机中研磨20重量份活性化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂,得到细碎悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I)粉剂(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。现行方法是挤出、喷雾干燥或流化床方法。这得到活性化合物含量为0.5重量%的不经稀释而施用的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到活性化合物含量为10重量%的不经稀释而施用的产品。
通常将水溶性浓缩物(LS)、悬浮液(FS)、粉剂(DS)、水分散性和水溶性粉末(WS、SS)、乳液(ES)、乳油(EC)和凝胶配制剂(GF)用于种子处理。这些配制剂可以未稀释形式或优选以稀释形式施用于种子上。施用可以在播种前进行。
活性化合物可以直接、以其配制剂形式或由其制备的使用形式(如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒),借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳油、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。或者还可以制 备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
活性化合物在即用制剂中的浓度可以在较宽范围内变化。它们通常为0.0001-10%,优选0.01-1%。
活性化合物还可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以在没有添加剂的情况下施用活性化合物。
可以向活性化合物中加入各种类型的油、润湿剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂,合适的话恰在紧临使用之前加入(桶混合)。这些组合物通常以1∶100-100∶1,优选1∶10-10∶1的重量比与本发明组合物混合。
就此而言下列物质为特别合适的辅助剂:有机改性的聚硅氧烷,例如Break Thru S 醇烷氧基化物,例如Atplus Atplus MBA Plurafac LF 和Lutensol ON EO-PO嵌段聚合物,例如PluronicRPE 和Genapol 醇乙氧基化物,例如Lutensol XP 以及磺基琥珀酸二辛酯钠,例如Leophen
本发明组合物还可以杀真菌剂的施用形式与其它活性化合物一起存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或肥料一起存在。将化合物I或包含它们的组合物与一种或多种其它活性化合物,尤其是杀真菌剂混合时,在许多情况下可以拓宽活性谱或防止产生抗药性。在许多情况下得到协同增效作用。
因此,本发明此外还提供了至少一种式I的唑基甲基环氧乙烷,尤其是本发明作为优选公开的唑基甲基环氧乙烷和/或其可农用酸加成盐或金属盐与至少一种其他杀真菌、杀虫、除草和/或生长调节活性化合物的组合,其中可能发生协同增效作用。
本发明还提供了一种农药组合物,其包含至少一种式I化合物,尤其是作为优选描述于本说明书中的式I化合物和/或其可农用的酸加成盐或金属盐和至少一种固体或液体载体。这种农药组合物可包含至少一种其它杀真菌、杀虫和/或除草活性的化合物,其中也可能发生协同增效作用。
本发明化合物可以与其一起使用的下列L杀真菌剂用来说明可能的组合但不限制它们:
列L:
嗜球果伞素类(Strobilurins)
-腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、肟菌酯(trifloxystrobin)、肟醚菌胺(orysastrobin)、(2-氯-5-[1-(3-甲基苄氧亚氨基)乙基]苄基)氨基甲酸甲酯、(2-氯-5-[1-(6-甲基吡啶-2-基甲氧基亚氨基)乙基]苄基)氨基甲酸甲酯、2-(邻-(2,5-二甲基苯氧基亚甲基)苯基)-3-甲氧基丙烯酸甲酯;
L-2
羧酰胺类
-羧酰苯胺类:苯霜灵(benalaxyl)、麦锈灵(benodanil)、啶酰菌胺(boscalid)、萎锈灵(carboxin)、丙氧灭绣胺(mepronil)、呋菌胺(fenfuram)、环酰菌胺(fenhexamid)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、氧化萎锈灵(oxycarboxin)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)、噻酰菌胺(tiadinil)、N-(4’-溴联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4’-三氟甲基联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(4’-氯-3’-氟联苯-2-基)-4-二氟甲基-2-甲基噻唑-5-甲酰胺、N-(3’,4’-二氯-4-氟联苯-2-基)-3-二氟甲基-1-甲基吡唑-4-甲酰胺、N-(2-氰基苯基)-3,4-二氯异噻唑-5-甲酰胺;
-羧酸吗啉化物:烯酰吗啉(dimethomorph)、氟吗啉(flumorph);
-苯甲酰胺类:氟联苯菌(flumetover)、fluopicolide(氟吡菌胺(picobenzamid))、苯酰菌胺(zoxamide);
-其他羧酰胺:氯环丙酰胺(carpropamid)、双氯氰菌胺(diclocymet)、双炔酰菌胺(mandipropamid)、N-(2-(4-[3-(4-氯苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-甲烷磺酰基氨基-3-甲基丁酰胺、N-(2-(4-[3-(4-氯 苯基)丙-2-炔氧基]-3-甲氧基苯基)乙基)-2-乙烷磺酰基氨基-3-甲基丁酰胺;
唑类
-三唑类:双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、烯菌灵(enilconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、氟硅唑(flusilazole)、喹唑菌酮(fluquinconazole)、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)、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)、唑菌醇(triadimenol)、三唑酮(triadimefon)、戊叉唑菌(triticonazole);
-咪唑类:氰霜唑(cyazofamid)、烯菌灵(imazalil)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole);
-苯并咪唑类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole);
-其他:噻唑菌胺(ethaboxam)、氯唑灵(etridiazole)、土菌消(hymexazole);
含氮杂环基化合物
-吡啶类:氟啶胺(fluazinam)、啶斑肟(pyrifenox)、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶;
-嘧啶类:磺嘧菌灵(bupirimate)、环丙嘧啶(cyprodinil)、嘧菌腙(ferimzone)、异嘧菌醇(fenarimol)、嘧菌胺(mepanipyrim)、氟苯嘧啶醇(nuarimol)、二甲嘧菌胺(pyrimethanil);
-哌嗪类:嗪氨灵(triforine);
-吡咯类:氟噁菌(fludioxonil)、拌种咯(fenpiclonil);
-吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
-二羧酰亚胺类:异丙定(iprodione)、杀菌利(procymidone)、烯菌酮 (vinclozolin);
-其他:噻二唑素(acibenzolar-S-methyl)、敌菌灵(anilazine)、克菌丹(captan)、敌菌丹(captafol)、棉隆(dazomet)、哒菌清(diclomezine)、氰菌胺(fenoxanil)、灭菌丹(folpet)、苯锈啶(fenpropidin)、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异噻菌酮(octhilinone)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、三环唑(tricyclazole)、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、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N,N-二甲基-3-(3-溴-6-氟-2-甲基吲哚-1-磺酰基)-[1,2,4]三唑-1-磺酰胺;
氨基甲酸盐和二硫代氨基甲酸盐
-二硫代氨基甲酸盐类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram)、威百亩(metam)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
-氨基甲酸盐类:乙霉威(diethofencarb)、flubenthiavalicarb、异丙菌胺(iprovalicarb)、百维灵(propamocarb)、3-(4-氯苯基)-3-(2-异丙氧羰基氨基-3-甲基丁酰氨基)丙酸甲酯、N-(1-(1-(4-氰基苯基)乙烷磺酰基)丁-2-基)氨基甲酸4-氟苯基酯;
其他杀真菌剂
-胍类:多果定(dodine)、双胍辛醋酸盐(iminoctadine)、双胍盐(guazatine);
-抗生素类:春雷素(kasugamycin)、多氧霉素(polyoxins)、链霉素(streptomycin)、井冈霉素(validamycin A);
-有机金属化合物类:三苯基锡盐;
-含硫的杂环基化合物:稻瘟灵(isoprothiolane)、二噻农(dithianon);
-有机磷化合物:克瘟散(edifenphos)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos)、甲基立枯磷(tolclofos-methyl)、亚磷酸及其盐;
-有机氯化合物:甲基托布津(thiophanate-methyl)、百菌清 (chlorothalonil)、抑菌灵(dichlofluanid)、对甲抑菌灵(tolylfluanid)、磺菌胺(flusulfamide)、四氯苯酞(phthalide)、六氯苯(hexachlorobenzene)、戊菌隆(pencycuron)、五氯硝基苯(quintozene);
-硝基苯基衍生物:乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton);
-无机活性化合物:波尔多液(Bordeaux混合物)、醋酸铜、氢氧化铜、王铜、碱式硫酸铜、硫;
其他:螺噁茂胺(spiroxamine)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、苯菌酮(metrafenone)。
合成实施例
实施例1
1)合成2-氯-1-(2,4,5-三氟苯基)乙酮
将N-氯琥珀酰亚胺(11.9g,89.3mmol)加入2,4,5-三氟苯乙酮(14.9g,85.0mmol)在乙酸(150ml)中的溶液中。将反应混合物在116℃下搅拌5小时,冷却至室温并用氢氧化钠水溶液中和。用乙酸乙酯(2×40ml)萃取水相。将合并的有机相经硫酸钠干燥,并蒸除溶剂。通过柱色谱(硅胶,己烷/二氯甲烷7∶3)提纯残留物。将合适的级分合并,得到白色固体形式的2-氯-1-(2,4,5-三氟苯基)乙酮(9.5g,54%)。
H-NMR(300MHz,CDCl3):δ7.88-7.79(m,1H),7.11-7.02(m,1H),4.96(d,J=3.2Hz,2H)。
2)合成1-氯-2-(2,4,5-三氟苯基)-3-(4-氟苯基)丙烷-2-醇
将镁屑(415mg,16.5mmol)和碘加入4-氟苄基氯(238mg,1.64mmol)在无水乙醚(20ml)中的溶液中。将反应混合物缓慢温热直至碘颜色消失并通过回流溶剂显示反应开始。滴加入剩下的4-氟苄基氯(2.14g,11.7mmol),以使反应混合物保持回流。在加料结束之后,将混合物在室温下另外搅拌2小时,然后冷却至0℃。在该温度下,滴加入在无水甲苯(10ml)中的2-氯-1-(2,4,5-三氟苯基)乙酮(3.1g,14.8mmol)。然后将混合物温热至室温并另外搅拌3小时。在此时间之后,将混合物又冷却至0℃,加入饱和氯化铵水溶液(10ml)。取出有机相,并用乙酸乙酯(2×20ml)萃取水相。将合并的 有机萃取物经硫酸钠干燥并除去溶剂。将如此得到的粗产物(5.0g)不经提纯而用于下面的反应步骤。
3)合成(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-2,4,5-三氟苯
在0℃下,首先将乙酸酐(1.8ml,14.8mmol),然后将浓硫酸(0.1ml,1.90mmol)加入1-氯-2-(2,4,5-三氟苯基)-3-(4-氟苯基)丙烷-2-醇(5.0g,约15.7mmol)在1,4-二噁烷/THF混合物(44ml,10∶1)中的溶液中。然后将反应混合物温热至室温,另外搅拌18小时,随后再冷却至0℃。在该温度下,加入饱和氯化钠溶液(20ml),并用氢氧化钠水溶液(6.2ml,50重量%)中和混合物。用乙酸乙酯(3×20ml)萃取所得混合物,将有机相合并,用水(2×30ml)洗涤并在硫酸钠上干燥。在过滤并在减压下除去溶剂之后,通过柱色谱(硅胶,己烷)提纯残留物。将合适的级分合并,得到以无色油形式的(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-2,4,5-三氟苯(490mg,10%,经2步)。
1H NMR(300MHz,CDCl3):δ7.45-7.41(m,2H),7.16-7.10(m,2H),7.00-6.92(m,2H),6.74(s,1H),4.51(s,2H)。
4)合成反-2-(2,4,5-三氟苯基)-2-(氯甲基)-3-(4-氟苯基)环氧乙烷
将马来酸酐(1.5g,16.3mmol)和过氧化氢水溶液(0.5ml浓度为50%的溶液,16.3mmol)加入(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-2,4,5-三氟苯(490mg,1.6mmol)在乙酸(20ml)中的溶液中。将反应混合物在40℃下搅拌18小时,然后冷却至室温,加入水(20ml)和硫代硫酸钠水溶液(浓度为10%的溶液,4ml)。用二氯甲烷(3×15ml)萃取水相并用氯化钠溶液(2×10ml)洗涤合并的有机相。将有机相在硫酸钠上干燥并过滤,并蒸除溶剂。通过柱色谱(硅胶,25∶1己烷/乙酸乙酯)提纯如此得到的残留物。将合适的级分合并,得到以无色固体形式的目标化合物(320mg,62%)。
1H NMR(300MHz,CDCl3):δ7.44-7.35(m,3H),7.13(t,J=8.6Hz,2H),7.03-6.95(m,1H),4.20(s,1H),3.78(d,J=12.0Hz,1H),3.37(d,J=12.0Hz,1H)。
5)合成1-[(反)-2-(2,4,5-三氟苯基)-3-(4-氟苯基)环氧乙烷-2-基]甲基]-1H-1,2,4-三唑
在室温下,将1,2,4-三唑(209mg,3mmol)和氢化钠(75mg,3.1mmol) 加入反-2-(2,4,5-三氟苯基)-2-(氯甲基)-3-(4-氟苯基)环氧乙烷(320mg,1.0mmol)在无水N,N-二甲基甲酰胺(20ml)中的溶液中。将混合物在75℃下搅拌18小时。然后将混合物冷却至室温,用乙酸乙酯(20ml)稀释并用氯化钠溶液(3×15ml)洗涤。移出有机相,在硫酸钠上干燥并过滤,并蒸除溶剂。通过柱色谱(硅胶,7∶3己烷/乙酸乙酯)提纯如此得到的残留物。将合适的级分合并,得到以无色固体形式的目标化合物(121mg,35%)。
1H NMR(300MHz,丙酮-d6):δ7.89(s,1H),7.82(s,1H),7.52-7.48(m,2H),7.18(t,J=8.0Hz,2H),7.09-6.93(m,2H),4.64(d,J=15.0Hz,1H),4.21(s,1H),4.04(d,J=15.0Hz,1H)。
实施例2
1)合成2-氯-1-(3,4,5-三氟苯基)乙酮
将N-氯琥珀酰亚胺(11.9g,89.1mmol)加入3,4,5-三氟苯乙酮(14.9g,85.6mmol)在乙酸(150ml)中的溶液中。将反应混合物在116℃下搅拌4.5小时,冷却至室温并用氢氧化钠水溶液中和。用乙酸乙酯(2×40ml)萃取水相。将合并的有机相经硫酸钠干燥,并蒸除溶剂。通过柱色谱(硅胶,己烷/二氯甲烷7∶3)提纯残留物。将合适的级分合并,得到白色固体形式的2-氯-1-(3,4,5-三氟苯基)乙酮(9.2g,53%)。
H-NMR(300MHz,CDCl3):δ7.66-7.61(m,2H),4.57(s,2H)。
2)合成1-氯-2-(3,4,5-三氟苯基)-3-(4-氟苯基)丙烷-2-醇
将镁屑(398mg,16.6mmol)和碘加入4-氟苄基氯(250mg,1.55mmol)在无水乙醚(25ml)中的溶液中。将反应混合物缓慢温热直至碘颜色消失并通过回流溶剂显示反应开始。滴加入剩下的4-氟苄基氯(2.80g,13.5mmol),以使反应混合物保持回流。在加料结束之后,将混合物在室温下另外搅拌2小时,然后冷却至0℃。在该温度下,滴加入在无水甲苯(10ml)中的2-氯-1-(3,4,5-三氟苯基)乙酮(2.36g,14.3mol)。然后将混合物温热至室温并另外搅拌3小时。在此时间之后,将混合物又冷却至0℃,加入饱和氯化铵水溶液(10ml)。分离有机相,并用乙酸乙酯(2×20ml)萃取水相。将合并的有机萃取物经硫酸钠干燥并除去溶剂。将如此得到的粗产物(5.0g)不经提纯而用于下面的反应步骤。
3)合成(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-3,4,5-三氟苯
在0℃下,首先将乙酸酐(1.8ml,14.8mmol),然后将浓硫酸(0.1ml,1.90mmol)加入1-氯-2-(3,4,5-三氟苯基)-3-(4-氟苯基)丙烷-2-醇(5.0g,约15.7mmol)在1,4-二噁烷/THF混合物(44ml,10∶1)中的溶液中。然后将反应混合物温热至室温,另外搅拌18小时,随后再冷却至0℃。在该温度下,加入饱和氯化钠溶液(20ml),并用氢氧化钠水溶液(6.2ml,50重量%)中和混合物。用乙酸乙酯(3×20ml)萃取混合物,将有机相合并,用水(2×30ml)洗涤并在硫酸钠上干燥。在过滤并在减压下除去溶剂之后,通过柱色谱(硅胶,己烷)提纯残留物。将合适的级分合并,得到以无色油形式的(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-3,4,5-三氟苯(814mg,19%,经2步)。
1H NMR(300MHz,CDCl3):δ7.62-7.59(m,1H),7.47-7.44(m,1H),7.37-7.32(m,2H),7.27-7.22(m,2H),7.05(s,1H),4.42(s,2H)。
4)合成反-2-(3,4,5-三氟苯基)-2-(氯甲基)-3-(4-氟苯基)环氧乙烷
将马来酸酐(554g,5.6mmol)和过氧化氢水溶液(0.1ml浓度为50%的溶液,5.6mmol)加入(Z)-1-[3-氯-1-(4-氟苯基)丙-1-烯-2-基]-3,4,5-三氟苯(170mg,0.5mmol)在乙酸(10ml)中的溶液中。将反应混合物在40℃下搅拌18小时,然后冷却至室温,加入水(20ml)和硫代硫酸钠水溶液(浓度为10%的溶液,4ml)。用二氯甲烷(3×15ml)萃取水相并用氯化钠溶液(2×10ml)洗涤合并的有机相。将有机相在硫酸钠上干燥并过滤,并蒸除溶剂。
通过柱色谱(硅胶,25∶1己烷/乙酸乙酯)提纯如此得到的残留物。将合适的级分合并,得到以无色固体形式的反-2-(3,4,5-三氟苯基)-2-(氯甲基)-3-(4-氟苯基)环氧乙烷(135mg,75%)。
1H NMR(300MHz,CDCl3):δ7.40-7.35(m,2H),7.19-7.09(m,4H),4.09(s,1H),3.76(d,J=12.0Hz,1H),3.53(d,J=12.0Hz,1H)。
5)合成1-[(反)-2-(3,4,5-三氟苯基)-3-(4-氟苯基)环氧乙烷-2-基]甲基]-1H-1,2,4-三唑
在室温下,将1,2,4-三唑(88mg,1.2mmol)和氢化钠(31mg,1.3mmol)加入反-2-(3,4,5-三氟苯基)-2-(氯甲基)-3-(4-氟苯基)环氧乙烷(135mg,0.4mmol)在无水N,N-二甲基甲酰胺(10ml)中的溶液中。将混合物在50℃下搅拌18小时。然后将混合物冷却至室温,用乙酸乙酯(20ml)稀释并用氯化钠溶液(3×15ml)洗涤。移出有机相,在硫酸钠上干燥并过滤,并蒸除溶剂。通过柱色谱(硅胶,7∶3 己烷/乙酸乙酯,然后硅胶,9∶1 二氯甲烷/乙酸乙酯)提纯如此得到的残留物。将合适的级分合并,得到以无色固体形式的目标化合物(33mg,22%)。
1H NMR(300MHz,丙酮-d6):δ7.91(s,1H),7.84(s,1H),7.47-7.42(m,2H),7.16(t,J=9.0Hz,2H),7.06-7.01(m,2H),4.68(d,J=15.0Hz,1H),4.12(s,1H),4.13(d,J=15.0Hz,1H)。
类似于这些制备方法,以具有三唑基甲基取代基和环B的顺式排列的外消旋体制备了表8的通式I的化合物:
表8
化合物 编号 | A | B | 物理数据FP[℃],1H-NMR (300MHz,CDCl3) |
8.1 | 3,4,5-三氟苯基 | 2-甲基苯基 | 7.81(2H),7.46(1H),7.33(2H), 7.23(1H),7.10(2H),4.67(1H), 4.09(1H),4.06(1H),2.30(3H) |
8.2 | 3,4,5-三氟苯基 | 2-氯苯基 | 135-139 |
8.3 | 3,4,5-三氟苯基 | 2-氟苯基 | 118-120 |
8.4 | 3,4,5-三氟苯基 | 4-氟苯基 | 103-105 |
8.5 | 2,4,5-三氟苯基 | 4-氟苯基 | 140-143 |
8.6 | 2,4,5-三氟苯基 | 2-氯苯基 | 134-136 |
8.7 | 2,4,5-三氟苯基 | 2-甲基苯基 | 7.91(1H),7.79(1H),7.51(1H), 7.31(3H),7.05(2H),4.73(1H), 4.18(1H),3.99(1H),2.44(3H) |
生物试验
温室
制备活性化合物
使用溶剂/乳化剂体积比为99/1的丙酮和/或DMSO与乳化剂Wettol EM 31(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)的混合物将活性化合物单独或联合配成包含25mg活性化合物并配成10ml的储备溶液。然后将该混合物用水配成100ml。将该储备溶液用所述溶剂/乳化剂/水混合物稀释至下述活性化合物浓度。
应用实施例1-对小麦上的小麦叶锈菌(Puccinia recondita)(小麦褐锈病)的保护活性(Puccrt P1)
将盆栽小麦秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。第二天将处理植物用小麦褐锈病(小麦叶锈菌)的孢子悬浮液接种。然后将植物在20-22℃的高大气湿度室中(90-95%)放置24小时。在此期间孢子萌发并且芽管穿透到叶组织中。第二天,将试验植物放回温室中并在温度为20-22℃且相对大气湿度为65-70%的温室中再培养7天。然后肉眼测定锈病真菌在叶子上的发展程度。
在该试验中,用包含63ppm表8的活性化合物8.5、8.6、8.7、8.1或8.2的活性化合物含水制剂处理的植物显示出至多10%的侵染,而未处理植物90%被侵染。
应用实施例2-对黄瓜叶上由单丝壳白粉菌引起的霉病的活性,保护性施用(Sphrfu P1)
将子叶阶段的盆栽黄瓜秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。在喷雾涂层干燥之后20小时,将植物用黄瓜霉病(单丝壳白粉菌)的含水孢子悬浮液接种。然后将植物在温度为20-24℃且相对大气湿度为60-80%的温室中培养7天。然后用肉眼以侵染百分数测定霉病在子叶面积上的发展程度。
在该试验中,用包含63ppm表8的活性化合物8.6、8.7、8.1和8.2的活性化合物含水制剂处理的植物显示出至多7%的侵染,而未处理植物90%被侵染。
对比试验
温室
制备活性化合物
使用溶剂/乳化剂体积比为99/1的丙酮和/或DMSO与乳化剂Wettol EM 31(基于乙氧基化烷基酚的具有乳化和分散作用的润湿剂)的混合物将活性化合物单独或联合配成包含25mg活性化合物并配成10ml的储备溶液。然后将该混合物用水配成100ml。将该储备溶液用所述溶剂/乳化剂/水混合物稀释至下述活性化合物浓度。
对比例1-对由单丝壳白粉菌引起的黄瓜叶上的霉病的活性,保护性施用(Sphrfu P1)
将子叶阶段的盆栽黄瓜秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。在喷雾涂层干燥之后20小时,将植物用黄瓜霉病(单丝壳白粉菌)的含水孢子悬浮液接种。然后将植物在温度为20-24℃且相对大气湿度为60-80%的温室中培养7天。然后用肉眼以侵染百分数测定霉病在子叶面积上的发展程度。
表9
从表9的值可看出,与结构最类似的现有技术化合物EP-A 0421125的化合物B 255相比,本发明化合物8.7具有显著更好的杀真菌活性。对比例2-对大麦网斑内脐蠕孢引起的大麦网斑病活性,1天保护性施用(Pyrnte pPl)
将盆栽大麦秧苗的叶子用活性化合物浓度如下所述的含水悬浮液喷雾至滴流点。在喷雾涂层干燥之后24小时,将测试植物用大麦网斑内脐蠕孢,网斑病病原体的含水孢子悬浮液接种。然后将测试植物放置在温度为20-24℃且相对大气湿度为95-100%的温室中。6天后,用肉眼以侵染百分 数测定病害在整个叶面积上的发展程度。
表10
从表10的值可看出,与结构最类似的现有技术化合物EP-A 0196038的化合物编号8相比,本发明化合物8.6显示显著更好的杀真菌活性。
Claims (6)
2.根据权利要求1的化合物,其中A为2,4,6-三氟苯基、3,4,5-三氟苯基或2,4,5-三氟苯基。
3.根据权利要求1或2的式I化合物或其酸加成盐或金属盐在防治植物病原性真菌中的用途。
4.一种作物保护组合物,包含固体或液体载体和根据权利要求1或2的式I化合物和/或其酸加成盐或金属盐。
5.包含至少一种根据权利要求1或2的式I化合物和/或其酸加成盐或金属盐的种子。
6.一种防治植物病原性真菌的方法,其中用有效量的根据权利要求1或2的式I化合物或其酸加成盐或金属盐处理真菌或需要防止真菌侵袭的材料、植物、土壤或种子。
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BRPI0713678A2 (pt) * | 2006-06-23 | 2012-10-23 | Basf Se | compostos, uso de compostos, composição para a proteção de cultura, semente, e, processo para combater fungos fitopatogênicos |
DE502007002119D1 (de) * | 2006-07-05 | 2010-01-07 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
ATE496912T1 (de) * | 2006-07-05 | 2011-02-15 | Basf Se | Azolylmethyloxirane, ihre verwendung zur bekämpfung von pflanzenpathogenen pilzen sowie sie enthaltende mittel |
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JP2011507815A (ja) * | 2007-12-19 | 2011-03-10 | ビーエーエスエフ ソシエタス・ヨーロピア | アゾリルメチルオキシラン類、それらの使用およびそれらを含む組成物 |
BRPI0821746A2 (pt) * | 2007-12-19 | 2015-06-16 | Basf Se | Composto, uso do mesmo, composição, semente, método para controlar fungos fitopatogênicos, medicamento, e, processos para preparar um antimicótico e para preparar compostos |
CN102802416A (zh) | 2009-06-18 | 2012-11-28 | 巴斯夫欧洲公司 | 杀真菌混合物 |
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-
2007
- 2007-06-14 CN CN200780023501XA patent/CN101479260B/zh not_active Expired - Fee Related
- 2007-06-14 JP JP2009515834A patent/JP2009541250A/ja not_active Ceased
- 2007-06-14 BR BRPI0713131-3A patent/BRPI0713131A2/pt not_active IP Right Cessation
- 2007-06-14 WO PCT/EP2007/055870 patent/WO2007147769A1/de active Application Filing
- 2007-06-14 DE DE502007002350T patent/DE502007002350D1/de active Active
- 2007-06-14 US US12/305,730 patent/US20100167924A1/en not_active Abandoned
- 2007-06-14 AT AT07730149T patent/ATE452131T1/de active
- 2007-06-14 EP EP07730149A patent/EP2035414B1/de not_active Not-in-force
- 2007-06-22 PE PE2007000806A patent/PE20080990A1/es not_active Application Discontinuation
- 2007-06-22 TW TW096122563A patent/TW200808178A/zh unknown
- 2007-06-22 CL CL2007001843A patent/CL2007001843A1/es unknown
- 2007-06-22 AR ARP070102767A patent/AR061610A1/es unknown
-
2012
- 2012-05-14 US US13/470,426 patent/US20120225777A1/en not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5162357A (en) * | 1989-09-09 | 1992-11-10 | Basf Aktiengesellschaft | Fungicidal azolylmethyloxiranes |
Also Published As
Publication number | Publication date |
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US20120225777A1 (en) | 2012-09-06 |
PE20080990A1 (es) | 2008-10-03 |
ATE452131T1 (de) | 2010-01-15 |
CL2007001843A1 (es) | 2008-01-18 |
TW200808178A (en) | 2008-02-16 |
US20100167924A1 (en) | 2010-07-01 |
DE502007002350D1 (de) | 2010-01-28 |
BRPI0713131A2 (pt) | 2012-04-17 |
AR061610A1 (es) | 2008-09-10 |
JP2009541250A (ja) | 2009-11-26 |
CN101479260A (zh) | 2009-07-08 |
EP2035414B1 (de) | 2009-12-16 |
WO2007147769A1 (de) | 2007-12-27 |
EP2035414A1 (de) | 2009-03-18 |
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