CN1255040A - 防治有害真菌的方法 - Google Patents
防治有害真菌的方法 Download PDFInfo
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- CN1255040A CN1255040A CN98804796A CN98804796A CN1255040A CN 1255040 A CN1255040 A CN 1255040A CN 98804796 A CN98804796 A CN 98804796A CN 98804796 A CN98804796 A CN 98804796A CN 1255040 A CN1255040 A CN 1255040A
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- Prior art keywords
- alkyl
- compound
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- haloalkyl
- acid
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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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
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Abstract
一种防治有害真菌的方法,其中使用有效量的通式Ⅰ的双肟或其盐或加成物处理真菌或处理欲使其免受这些真菌侵染的材料、植物、土壤或种子,其中角标和取代基具有如下含意:R1是卤素、烷基或卤代烷基;R2是氨基、硝基、卤素、烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基、烷基氨基、二烷基氨基、烷基氨基羰基,任选取代的苯基、苯氧基或苯硫基;n是0、1、2或3;R3是烷基、卤代烷基、链烯基、卤代烯基、炔基、卤代炔基或苯基烷基。本发明还涉及化合物(Ⅰ)用于制备适于防治有害真菌的组合物的用途。
Description
本发明涉及一种防治有害真菌的方法,其特征在于,使用有效量的通式I的双肟或其盐或加成物处理真菌或处理欲使其免受这些真菌侵染的材料、植物、土壤或种子,其中角标和取代基具有如下含意:R1卤素、C1-C6-烷基或C1-C4-卤代烷基;R2是氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基氨基、二-C1-C4-烷基氨基、C1-C4-烷基氨基羰基,
苯基、苯氧基或苯硫基,其中这些基团的苯基可以是部分或全部卤代的和/或携带1至3个下列基团:氰基、甲酰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷基羰基、C1-C4-烷氧基、C1-C4-卤代烷氧基、苯基或萘基;n是0、1、2或3,其中当n是2或3时,基团R2可以是不同的;R3是C1-C10-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-卤代烯基、C3-C6-炔基、C3-C6-卤代炔基或苯基-C1-C4-烷基。
此外,本发明涉及化合物I制备适合于防治有害真菌的组合物的用途。
由文献(参见WO-A 95/18,789;WO-A 95/21,153;WO-A95/21,154;WO-A 95/21,156;WO-A 96/06,072;WO-A 96/16,026;WO-A 96/16,030;WO-A 97/01,530;WO-A 97/02,255;DE申请号19 540989;DE申请号19 545 878;DE申请号19 548 370)已知本文开头定义的式I双肟作为中间产物用于制备式A类的杀真菌活性物质:
然而,除该化合物作为中间产物的用途外,从这些文献中不能推断出该双肟的其它用途。
此外,在PCT/EP 96/01,306中描述了化合物I这类几乎是纯异构体的双肟的制备方法。由其用途来看,这些参考文献中均关注该化合物作为制备(A)类化合物的中间产物的能力。
本发明的任务是提供一种具有杀真菌性能的化合物。因此,发现已知的双肟适合于有效地防治有害真菌。
例如由WO-A 95/21,156中的相应说明可以获知定义化合物I时使用的集合名词的含意。
由防治有害真菌的这一确定的用途看来,其中R1是氟、氯或溴(特别是氯)或甲基、乙基、丙基或异丙基(特别是甲基或乙基)的化合物I是特别适合的。
此外,优选使用其中n表示1、2或3(特别是1或2)的化合物I。
在n是1的情况下,优选其中基团R2在苯环4位上键合的化合物I。
在n是2的情况下,优选其中基团R2在相对位2,4或3,4(特别是2,4)上键合的化合物I。
在n是3的情况下,优选其中基团R2在相对位2,4,5或2,4,6位(特别是2,4,5)上键合的化合物I。
特别适合的基团R2是卤素(特别是氟、氯和溴)、C1-C4-烷基(特别是甲基)、C1-C4-卤代烷基(特别是三氟甲基)、C1-C4-烷氧基(特别是甲氧基)、C1-C4-卤代烷氧基(特别是三氟甲氧基)、C1-C4-烷硫基(特别是甲硫基)、硝基和二甲基氨基。
此外,优选其中R2(优选基团R2之一)具有如下含意的化合物I:苯基、苯氧基或苯硫基(特别是苯基),其中这些基团的苯基优选可以携带1至3个下列基团:卤素(特别是氯和溴)、C1-C4-烷基(特别是甲基)、C1-C4-卤代烷基(特别是三氟甲基)、C1-C4-烷氧基(特别是甲氧基)和C1-C4-卤代烷氧基(特别是三氟甲氧基)。
同样特别优选其中至少一个R2基团表示卤素的化合物I。
优选其中基团R3具有如下含意的化合物I:
·C1-C10-烷基(特别的C1-C4-烷基),
·C3-C6-链烯基或C3-C6-卤代烯基(特别是C3-C4-链烯基,其可以携带1至3个(特别是1或2个)卤原子(特别是氯或溴)),
·C3-C6-炔基或C3-C6-卤代炔基(特别是C3-C4-炔基,其可以携带1至3个(特别是1或2个)卤原子(特别是氯或溴)),或
·苯基-C1-C4-烷基(特别是苄基)。
化合物I适合于作为杀真菌剂。其突出之处在于,它对广谱的植物病原真菌均有优异活性,特别是对属于子囊菌纲、担子菌纲、半知菌纲和藻状菌纲的真菌。这些化合物中某些具有内吸作用,且在作物保护中可以用作叶面和土壤杀真菌剂。
它们在防治各种作物如小麦、黑麦、大麦、燕麦、稻、玉米、牧草、香蕉、棉花、大豆类、咖啡、甘蔗、葡萄、水果、观赏植物和蔬菜(例如,黄瓜、菜豆、西红柿、土豆和胡瓜)以及这些作物的种子上的许多真菌方面特别有意义。
化合物I特别适合于防治下列植物病害:
·蔬菜和水果上的链格孢菌病害(Alternaria),
·草莓、葡萄、蔬菜和观赏植物上的灰霉病(Botrytis cinerea),
·花生褐斑病(Cercospora arachidicola),
·胡瓜白粉病(Erysiphe cichoracearum)和Sphaerothecafuliginea,
·禾谷类白粉病(Erysiphe graminis),
·各种作物上的镰刀菌病害(Fusarium)和轮枝孢菌病害(Verticillium),
·禾谷类网斑病(Helminthosporium),
·香蕉上的球腔菌属病(Mycosphaerella),
·马铃薯和蕃茄晚疫病(Phytophthora infestans),
·葡萄霜霉病(Plasmopara viticola),
·苹果白粉病(Podosphaera leucotricha),
·小麦和大麦眼斑病(Pseudocercosporella herpotrichoides),
·啤酒花和黄瓜类霜霉病(Pseudoperonospora),
·禾谷类柄锈病(Puccinia),
·稻瘟病(Pyricularia oryzae),
·棉花、稻和草坪上的丝核病(Rhizoctonia),
·小麦颖枯病(Septoria nodorum),
·葡萄白粉病(Uncinula necator),
·禾谷类和甘蔗黑粉病(Ustilago),
·苹果黑星病(Venturia inaequalis)。
化合物I特别适合于防治白粉病(Erysiphe)和霜霉病(Plasmoparaviticola)。
此外,化合物I适合于在材料(例如木材、纸、涂料分散液、纤维或织物)防护和储存物的保护中防治有害真菌例如多变拟青霉(Paecilomyces variotii)。
式I化合物可以通过用杀真菌有效量的活性成分处理真菌或意欲保护使之免受真菌感染的植物、种子、材料或土壤而使用。施用可以是在材料、植物或种子受真菌感染前或后进行。
根据所需的效果类型,在作物保护中使用时,施用量是0.001至5.0,优选0.01至2,特别优选0.05至1千克活性化合物/公顷。
在处理种子时,活性化合物的一般需要量是0.001至0.1克,优选0.01克至0.05克/千克种子。
在材料或储存物保护中使用时,活性化合物的使用量取决于使用领域的特性和所需效果的类型。例如,在材料保护中通常的施用量是0.001克至2千克,优选0.005克至1千克活性化合物/立方米处理材料。
考虑到氮原子的碱性性质,化合物I能够与酸和金属离子形成盐或加成物,并且不但可以使用纯的化合物而且可以使用以盐或加成物形式存在的化合物。
无机酸的实例包括氢卤酸例如氢氟酸,氢氯酸,氢溴酸和氢碘酸,以及硫酸,磷酸和硝酸。
合适的有机酸包括例如甲酸、碳酸和链烷酸,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(含有1-20个碳原子的直链或支链烷基磺酸),芳基磺酸或芳基二磺酸(其上连接有一个或两个磺基的芳基(如苯基和萘基)),烷基膦酸(具有1-20个碳原子的直链或支链烷基膦酸),芳基膦酸或芳基二膦酸(其上连接有一个或两个磷酸残基的芳基(例如苯基和萘基)),其中的烷基或芳基还可携带其它取代基,例如,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。
适当的金属离子尤为下列各族元素的离子:第一到第八副族元素(特别是铬,锰,铁,钴,镍,铜,锌),以及第二主族元素(特别是钙和镁),第三和第四主族元素(特别是铝,锡和铅)。
这些金属可以以它们可能具有的各种价态存在。
可以将化合物I和其盐转换成常规制剂如溶液、乳剂、悬浮剂、喷粉剂、粉剂、膏剂和颗粒剂。施用形式取决于各自的使用目的;在任一种情况下,须保证化合物I的分散尽可能的细微和均匀。
这些制剂可以用已知的方式制备,例如通过将活性化合物用溶剂和/或载体来增容,如果需要,采用乳化剂和分散剂,如果用水作稀释剂,也可以用其它的有机溶剂作助溶剂。对此适合的辅助剂主要是溶剂,如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己酮)、胺类(例如乙醇胺、二甲基甲酰胺)和水;载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎的合成矿物质(例如高分散的硅酸、硅酸盐);乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木质素亚硫酸盐废液或甲基纤维素。
适合的表面活性物质是木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸、烷基芳基磺酸、烷基硫酸、烷基磺酸、脂肪醇硫酸的碱金属盐、碱土金属盐、铵盐和脂肪酸及其碱金属、碱土金属盐,硫酸化脂肪醇乙二醇醚的盐,磺化萘和萘衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基苯酚醚、乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚,烷基苯酚聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇、脂肪醇/环氧乙烷缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚、乙氧基化聚氧丙烯,月桂醇聚乙二醇醚乙缩醛、山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
适合于制备直接可喷洒用溶液、乳剂、膏剂或油分散剂的物质是中至高沸点的矿物油馏份如煤油或柴油,还有煤焦油和植物或动物油,脂族、环状和芳族烃例如苯、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、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂例如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉剂、撒施材料和喷粉剂可以通过将活性物质与固体载体混合或一起研磨而生产。
颗粒剂例如包衣、浸渍和匀质颗粒可以通过将活性物质粘合在固态载体上来制备。固态载体是矿质土类如硅胶、硅酸、硅胶、硅酸盐、滑石、高岭土、粘土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、磨细的塑料、肥料,如硫酸铵、磷酸铵、硝酸铵、尿素和植物产品如谷类作物粉末、树皮、木材和坚果壳粉,纤维素粉末或其他固态载体。
通常,制剂包含0.01至95重量%、优选0.1至90重量%的活性成分。活性成分的纯度一般是90至100%,优选95至100%(根据NMR谱)。
配制制剂的实例是:I.将5重量份的本发明化合物与95重量份的细粉碎的高岭土均匀混合,由此获得喷粉剂,它包含5重量%的活性成分。II.将30重量份的本发明化合物与如下的混合物均匀混合:92重量份的粉状的硅胶和8重量份的石蜡油,该石蜡油预先喷涂到硅胶表面上。得到具有良好粘性的活性成分的制剂(包含按重量计23%的活性成分)。III.将10重量份的本发明化合物溶于如下混合物:90重量份的二甲苯、6重量份的8至10摩尔环氧乙烷与1摩尔油酸N-单乙醇酰胺的加成物、2重量份的十二烷基苯磺酸钙盐和2重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物(包含按重量计9%的活性成分)。IV.将20重量份的本发明化合物溶于如下混合物:60重量份的环己酮、30重量份的异丁醇、5重量份的7摩尔环氧乙烷与1摩尔异辛基苯酚的加成物和5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物(包含按重量计16%的活性成分)。V.将80重量份的本发明化合物与3重量份的二异丁基萘-α-磺酸钠盐、10重量份的来源于亚硫酸盐废液的木素磺酸钠盐和7重量份的粉状硅胶彻底混合,且在锤磨中磨碎混合物(包含按重量计80%的活性成分)。VI.90重量份的本发明化合物与10重量份的N-甲基-α-吡咯烷酮混合,得到一溶液,该溶液适合以微小雾滴的形式使用(包含按重量计90%的活性成分)。VII.将20重量份的本发明化合物溶于如下混合物:40重量份环己酮、30重量份的异丁醇、20重量份的7摩尔环氧乙烷与1摩尔异辛基苯酚的加成物和10重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物。将此溶液倒入并细分散于100,000重量份的水中,得到含有按重量计0.02%活性成分的水分散液。VIII.将20重量份的本发明化合物、3重量份的二异丁基萘-α-磺酸钠盐、17重量份的来源于亚硫酸盐废液的木素磺酸钠盐、60重量份的粉状硅胶彻底混合,并将混合物在锤磨中磨碎。将此混合物细分散于20,000重量份的水中,获得含按重量计0.1%的活性成分的喷雾混合物。
活性成分可以以其本身、其制剂形式或由之制备的使用形式,例如以可直接喷雾溶液、粉剂、悬浮剂或分散液、乳剂、油分散液、膏剂、喷粉剂、撒施材料或颗粒剂的形式,通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式主要取决于使用的目的;在每一种情况下,应确保本发明的活性化合物的分散尽可能的细微和均匀。
含水的施用形式可以通过加水,由乳油、膏剂或可湿性粉剂(可喷雾粉剂、油分散剂)制备。制备乳剂、膏剂或油分散液时,可通过加入润湿剂、粘合剂、分散剂或乳化剂,将物质本身或溶于油或溶剂的物质在水中均化。而且,也可以制备由活性物质、润湿剂、粘合剂、分散剂或乳化剂和可能的溶剂或油组成的浓缩物,该浓缩物适合于用水稀释。
在即可使用制剂中的活性成分浓度可以在相当宽的范围内变化。上述浓度通常是0.0001至10%,优选0.01至1%。
活性成分也可成功地用超低容量方法(ULV)使用,其中可能使用包含按重量计大于95%的活性化合物的制剂,甚至可能使用活性化合物本身而无须添加剂。
各种类型的油、除草剂、杀真菌剂、其它杀虫剂或杀细菌剂可以加入活性成分中,如果需要,在即将使用之前混入(桶混)。这些药剂可以与本发明组合物混合,混合重量比为1∶10至10∶1。
在作为杀真菌剂使用时,本发明组合物也可以与其它活性成分一同存在,例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或化肥一同存在。因此,化合物I或含该化合物的组合物与其它杀真菌剂相混合作为杀真菌剂使用时,在大多数情况下产生更宽的杀真菌作用谱。
下列杀真菌剂可与本发明化合物一起使用,列出它们旨在说明可能的组合,而非旨在限定之:
·硫磺,二硫代氨基甲酸盐类及其衍生物,如二甲基二硫代氨基甲酸铁(III),二甲基二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锰,乙二胺双二硫代氨基甲酸锰锌,二硫化四甲基秋兰姆,N,N-亚乙基双二硫代氨基甲酸锌的氨配合物,N,N′-亚丙基双二硫代氨基甲酸锌的氨配合物,N,N′-亚丙基双二硫代氨基甲酸锌,N,N′-聚亚丙基双(硫代氨基甲酰基)二硫化物;
·硝基衍生物,如二硝基-(1-甲基庚基)苯基巴豆酸酯,2-仲丁基-4,6-二硝基苯基-3,3-二甲基丙烯酸酯,碳酸2-仲丁基-4,6-二硝基苯基-异丙酯,5-硝基间苯二酸二异丙酯;
·杂环类物质,如2-十七烷基-2-咪唑啉乙酸酯,2,4-二氯-6-(邻-氯苯胺基)-均三嗪,O,O-二乙基邻苯二甲酰亚氨基硫代膦酸酯,5-氨基-1-[双(二甲基氨基)氧膦基]-3-苯基-1,2,4-三唑,2,3-二氰基-1,4-二硫代蒽醌,2-硫代-1,3-二硫杂环戊二烯并(dithiolo)[4,5-b]喹喔啉,1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯,2-甲氧基羰基氨基苯并咪唑,2-(呋喃基-(2))-苯并咪唑,2-(噻唑基-(4))-苯并咪唑,N-(1,1,2,2-四氯乙硫基)四氢邻苯二甲酰亚胺,N-三氯甲硫基四氢邻苯二甲酰亚胺,N-三氯甲硫基邻苯二甲酰亚胺;
·N-二氯氟甲硫基-N′,N′-二甲基-N-苯基硫酸二酰胺,5-乙氧基-3-三氯甲基-1,2,3-噻二唑,2-氰硫基甲硫基苯并噻唑,1,4-二氯-2,5-二甲氧基苯,4-(2-氯苯基亚肼基)-3-甲基-5-异噁唑酮,吡啶-2-硫代-1-氧化物,8-羟基喹啉和其铜盐,2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯,2,3-二氢-5-甲酰苯胺基-6-甲基-1,4-氧硫杂环己二烯-4,4-二氧化物,2-甲基-5,6-二氢-4H-吡喃-3-甲酰苯胺,2-甲基呋喃-3-甲酰苯胺,2,5-二甲基呋喃-3-甲酰苯胺,2,4,5-三甲基呋喃-3-甲酰苯胺,N-环己基-2,5-二甲基呋喃-3-甲酰胺,N-环己基-N-甲氧基-2,5-二甲基呋喃-3-甲酰胺,2-甲基苯甲酰苯胺,2-碘苯甲酰苯胺,N-甲酰基-N-吗啉-2,2,2-三氯乙基乙缩醛,哌嗪-1,4-亚基双-1-(2,2,2-三氯乙基)甲酰胺,1-(3,4-二氯苯胺基)-1-甲酰氨基-2,2,2-三氯乙烷;
·胺类如2,6-二甲基-N-十三烷基吗啉及其盐,2,6-二甲基-N-环十二烷基吗啉及其盐,N-[3-(对-叔丁基苯基)-2-甲基丙基]-顺-2,6-二甲基-吗啉,N-[3-(对-叔丁基苯基)-2-甲基丙基]哌啶,(8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲胺;
·唑类,如1-[2-(2,4-二氯苯基)-4-乙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,1-[2-(2,4-二氯苯基)-4-正丙基-1,3-二氧戊环-2-基乙基]-1H-1,2,4-三唑,N-(正丙基)-N-(2,4,6-三氯苯氧基乙基)-N′-咪唑基脲,1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮,1-(4-氯苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁醇,(2RS,3RS)-1-[3-(2-氯苯基)-2-(4-氟苯基)-环氧乙烷-2-基-甲基]-1H-1,2,4-三唑,1-[2-(2,4-二氯苯基)-戊基]-1H-1,2,4-三唑,2,4’-二氟-a-(1H-1,2,4-三唑基-1-甲基)-二苯甲醇,1-((双-(4-氟苯基)甲基甲硅烷基)-甲基)-1H-1,2,4-三唑,1-[2RS,4RS;-2RS,4SR-4-溴-2-(2,4-二氯苯基)-四氢呋喃基]-1H-1,2,4-三唑,2-(4-氯苯基)-3-环丙基-1-(1H-1,2,4-三唑-1-基)-丁-2-醇,(+)-4-氯-4-[4-甲基-2-(1H-1,2,4-三唑-1-基甲基)-1,3-二氧戊环-2-基]-苯基-4-氯苯基醚,(E)-(R,S)-1-(2,4-二氯苯基)-4,4-二甲基-2-(1H-1,2,4-三唑-1-基)戊-1-烯-3-醇,4-(4-氯苯基)-2-苯基-2-(1H-1,2,4-三唑基甲基)-丁腈,3-(2,4-二氯苯基)-6-氟-2-(1H-1,2,4-三唑-1-基)喹唑啉-4(3H)-酮,(R,S)-2-(2,4-二氯苯基)-1H-1,2,4-三唑-1-基)-己-2-醇,(1RS,5RS;1RS,5SR)-5-(4-氯苄基)-2,2-二甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇,(R,S)-1-(4-氯苯基)-4,4-二甲基-3-(1H-1,2,4-三唑-1-基甲基)戊-3-醇,(+)-2-(2,4-二氯苯基)-3-(1H-1,2,4-三唑基)-丙基-1,1,2,2-四氟乙基醚,(E)-1-[1-[4-氯-2-三氟甲基-苯基]-亚氨基)-2-丙氧基乙基]-1H-咪唑,2-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基甲基)-己腈;
·α-(2-氯苯基)-α-(4-氯苯基)-5-嘧啶甲醇,5-丁基-2-二甲氨基-4-羟基-6-甲基嘧啶,双-(对-氯苯基)-3-吡啶甲醇,1,2-双-(3-乙氧基羰基-2-硫脲基)苯,1,2-双-(3-甲氧基羰基-2-硫脲基)苯;
·Strobilurine如E-甲氧基亚氨基[α-(邻甲苯氧基)-邻-甲苯基]乙酸甲酯,E-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯,N-甲基-E-甲氧基亚氨基-[α-(2-苯氧基苯基)]乙酰胺,N-甲基-E-甲氧基亚氨基[α-(2,5-二甲基苯氧基)-邻-甲苯基]乙酰胺;
·苯胺基嘧啶类如N-(4,6-二甲基嘧啶-2-基)苯胺,N-[4-甲基-6-(1-丙炔基)嘧啶-2-基]苯胺,N-(4-甲基-6-环丙基嘧啶-2-基)苯胺;
·苯基吡咯类如4-(2,2-二氟-1,3-苯并间二氧杂环戊烯-4-基)吡咯-3-腈;
·肉桂酰胺类如3-(4-氯苯基)-3-(3,4-二甲氧基苯基)丙烯酰吗啉;
·以及各种杀真菌剂,如十二烷基乙酸胍,3-[3-(3,5-二甲基-2-氧基环己基)-2-羟基乙基]戊二酰亚胺,N-甲基-,N-乙基-(4-三氟甲基,-2-[3’,4’-二甲氧基苯基]-苯甲酰胺,六氯苯,DL-N-(2,6-二甲基苯基)-N-糠酰(2)-丙氨酸甲酯,DL-N-(2,6-二甲基苯基)-N-(2′-甲氧基乙酰基)丙氨酸甲酯,N-(2,6-二甲基苯基)-N-氯乙酰基-D,L-2-氨基丁内酯,DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯,5-甲基-5-乙烯基-3-(3,5-二氯苯基)-2,4-二氧代-1,3-噁唑烷,3-[3,5-二氯苯基-(-5-甲基-5-甲氧基甲基]-1,3-噁唑烷-2,4-二酮,3-(3,5-二氯苯基)-1-异丙基氨基甲酰基海因,N-(3,5-二氯苯基)-1,2-二甲基环丙烷-1,2-二甲酰亚胺,2-氰基-[N-(乙基氨基羰基)-2-甲氧基亚氨基]乙酰胺,N-(3-氯-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶。
合成实施例
采用随后合成实施例中描述的步骤,通过相应改变起始化合物来获得其它的化合物I。在所附的表中给出这样获得的化合物和其物理数据。1、1-[4-氯苯基]-丙烷-1,2-二酮-2-肟
在45克(0.27摩尔)4-氯苯基·乙基甲酮和500毫升甲苯的溶液中首先在-10至-20℃下滴加100毫升饱和的盐酸乙醚溶液,接着加入44.5克正丁腈在200毫升二乙醚中的溶液。在20至22℃下约24小时之后,将反应混合物倾倒在冰水中。分离有机相,用1N的氢氧化钠溶液洗涤三次和用3N的氢氧化钠溶液洗涤1次。合并氢氧化钠溶液相,用20%的硫酸酸化至pH=5。分离因此形成的沉淀物,并溶解在叔丁基甲基醚中。经硫酸钠干燥溶液,并在减压下除去溶剂。获得81.4克的黄色固体状产物。1H-NMR(CDCl3,δ(ppm)):2,2(s,3H);7,4(m,2H);7,8(m,2H);9,0(s,1H)2、4-氯苯基-[E/E,Z/E]-2-羟基亚氨基-1-甲氧基亚氨基丙烷
在81.4克1-[4-氯苯基]-丙烷-1,2-二酮-2-肟和500毫升甲醇的混合物中加入68.5克(0.82摩尔)0-甲基-羟胺-盐酸盐和97克(1.23摩尔)的吡啶。在22至25℃下约24小时之后,将反应混合物加入10%的盐酸中。使用叔丁基甲基醚萃取该混合物多次。合并有机相,用水洗涤,并经硫酸钠干燥。接着,在减压下除去溶剂。这样获得89.4克产物(异构体混合物)。3、4-氯苯基-[E/E]-2-羟基亚氨基-1-甲氧基亚氨基丙烷
在40℃下,在89.4克(0.39摩尔)4-氯苯基-[E/E,Z/E]-2-羟基亚氨基-1-甲氧基亚氨基丙烷于500毫升甲苯的溶液中缓慢地加入26.6克(0.2摩尔)的三氯化铝。在50℃下5小时和在20至22℃下24小时之后,将反应混合物加入冰和10%盐酸的混合物中。这样获得的混合物用叔丁基甲基醚萃取多次。合并有机相,用10%盐酸洗涤,接着用水洗涤,并干燥。接着,在减压下除去溶剂。这样获得50.6克无色固体状产物(熔点175至178℃;异构体比例98.5%E/E和1.5%Z/E)。1H-NMR(CDCl3,δ(ppm)):2,1(s,3H);4,0(s,3H);7,1(m,2H);7,3(m,2H);8,0(s,1H)表1:
对有害真菌的作用的实施例:
通过下列的试验可以显示式I化合物杀真菌的作用:
将活性成分制备成在如下混合物中的浓度为10%的乳剂:63%(重量)的环己酮和27%(重量)的乳化剂,并根据所需浓度用水稀释。1、对禾白粉病菌(Erysiphe graminis var.tritici)的作用
将小麦秧苗(品种:Fruehgold)的叶子首先用活性成分的含水制剂处理(施用量:250ppm)。约24小时后,将禾白粉病菌(Erysiphegraminis var.tritici)的孢子喷在植株上。接着,将以该方式处理的植株在20-22℃和75-80%相对湿度下温育7天。随后评价真菌发育的程度。
在此试验中,用本发明化合物I.5、I.15、I.19、I.20、I.21、I.22、I.27、I.28、I.36、I.42、I.63和I.76处理的植株显示出10%和更低的感病水平,而未处理(对照)的植株的感病水平为75%。2、对葡萄霜霉病菌(Plasmopara viticola)的作用
将盆栽葡萄(品种:Mueller Thurgau)的叶片用活性成分的含水制剂喷至滴流。为了评价该物质的持久作用,在喷雾液层干燥之后,将该植物在温室中放置7天。然后,首先用葡萄霜霉病菌的游动孢子的含水悬浮液接种叶片。之后首先在水蒸气饱和的温度为24℃的培养室中放置48小时,然后在20-30℃的温室中放置5天。然后再一次在潮湿的培养室中将该植放置16小时以加快孢子囊柄萌发。然后目测叶片背面的感染程度。
在此试验中,用250ppm的本发明化合物I.39、I.44和I.83处理的植株显示出15%和更低的感病水平,而未处理(对照)的植株的感病水平为70%。
Claims (6)
1、一种防治有害真菌的方法,其特征在于,使用有效量的通式I的双肟或其盐或加成物处理真菌或处理欲使其免受这些真菌侵染的材料、植物、土壤或种子,其中角标和取代基具有如下含意:R1卤素、C1-C6-烷基或C1-C4-卤代烷基;R2是氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基氨基、二-C1-C4-烷基氨基、C1-C4-烷基氨基羰基,
苯基、苯氧基或苯硫基,其中这些基团的苯基可以是部分或全部卤代的和/或携带1至3个下列基团:氰基、甲酰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷基羰基、C1-C4-烷氧基、C1-C4-卤代烷氧基、苯基或萘基;n是0、1、2或3,其中当n是2或3时,基团R2可以是不同的;R3是C1-C10-烷基、C1-C6-卤代烷基、C3-C6-链烯基、C3-C6-卤代烯基、C3-C6-炔基、C3-C6-卤代炔基或苯基-C1-C4-烷基。
2、根据权利要求1的方法,其特征在于,使用其中R1是氯、甲基、三氟甲基或乙基的权利要求1的式I化合物。
3、根据权利要求1的方法,其特征在于,使用其中至少一个R2基团表示卤素的权利要求1的式I化合物。
4、保护农作物使其免受有害真菌侵染的方法,其特征在于,使用0.001至5.0千克/公顷的权利要求1的式I化合物处理欲使其免受有害真菌侵染的农作物或其生长空间。
5、保护种子、材料或区域使其免受有害真菌侵染的方法,其特征在于,使用0.01至20克/立方米的权利要求1的式I化合物处理欲使其免受有害真菌侵染的种子、材料或区域。
6、权利要求1的式I化合物的用途,其用于制备适合于防治有害真菌的组合物。
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JP (1) | JP2001526701A (zh) |
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AT (1) | ATE213386T1 (zh) |
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US20100261396A1 (en) * | 2004-07-02 | 2010-10-14 | Dixon Timothy R | Insecticidally treated fabric having improved wash durability and insecticidal efficacy and method for its production |
US7625411B2 (en) * | 2004-07-02 | 2009-12-01 | Piedmont Chemical Industries I, LLC | Insecticidally treated fabric having improved wash durability and insecticidal efficacy and method for its production |
CA2663436A1 (en) * | 2006-10-04 | 2008-04-10 | Pfizer Products Inc. | Pyrido[4,3-d]pyrimidin-4(3h)-one derivatives as calcium receptor antagonists |
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JPH09508396A (ja) | 1994-02-04 | 1997-08-26 | ビーエーエスエフ アクチェンゲゼルシャフト | フェニルチオ酢酸誘導体、これを製造するための方法および中間生成物ならびにこれを含有する剤 |
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DE4441674A1 (de) | 1994-11-23 | 1996-05-30 | Basf Ag | Iminooxymethylenanilide, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
ATE201196T1 (de) | 1995-04-08 | 2001-06-15 | Basf Ag | Verfahren zur herstellung von weitgehend isomerenreinen alpha-bisoximen |
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DE19540989A1 (de) | 1995-11-03 | 1997-05-07 | Basf Ag | Pyridylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel |
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KR20010013090A (ko) | 2001-02-26 |
ZA984509B (en) | 1999-11-29 |
TW501910B (en) | 2002-09-11 |
BR9809472A (pt) | 2000-06-20 |
DK0984686T3 (da) | 2002-06-10 |
PT984686E (pt) | 2002-08-30 |
US6255352B1 (en) | 2001-07-03 |
IL131749A0 (en) | 2001-03-19 |
HUP0002076A2 (hu) | 2000-10-28 |
DE59803134D1 (de) | 2002-03-28 |
AU8017998A (en) | 1998-12-30 |
AU748963B2 (en) | 2002-06-13 |
EP0984686A1 (de) | 2000-03-15 |
JP2001526701A (ja) | 2001-12-18 |
AR015381A1 (es) | 2001-05-02 |
HUP0002076A3 (en) | 2001-02-28 |
CA2286716A1 (en) | 1998-12-03 |
EP0984686B1 (de) | 2002-02-20 |
WO1998053682A1 (de) | 1998-12-03 |
ATE213386T1 (de) | 2002-03-15 |
CO5050364A1 (es) | 2001-06-27 |
NZ337734A (en) | 2001-06-29 |
ES2172895T3 (es) | 2002-10-01 |
PL337167A1 (en) | 2000-07-31 |
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