CN1294852A - 嘧啶酮衍生物在控制不希望的微生物中的应用 - Google Patents
嘧啶酮衍生物在控制不希望的微生物中的应用 Download PDFInfo
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- CN1294852A CN1294852A CN 99123550 CN99123550A CN1294852A CN 1294852 A CN1294852 A CN 1294852A CN 99123550 CN99123550 CN 99123550 CN 99123550 A CN99123550 A CN 99123550A CN 1294852 A CN1294852 A CN 1294852A
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Abstract
式(Ⅰ)的嘧啶酮类衍生物非常适用于控制不希望的微生物,其中R1表示烷氧基,R2表示氢或烷基,R3表示烷基或苯基,以及R4表示任意取代的芳基、任意取代的杂芳基或任意取代的杂芳烷基。新的式(Ⅰa)的嘧啶酮类衍生物剂其制备方法,其中R1、R2和R3如上所定义,并且R6具有说明书中提及的含义。
Description
本发明涉及嘧啶酮衍生物在控制不希望的微生物中的新用途。本发明还涉及新的嘧啶酮衍生物及其制备方法。
某些2-芳氨基嘧啶酮衍生物是已知的(参见EP-A 0 636 615)。但是迄今为止,仅仅对这些化合物的除草及植物生长调节性质有所描述。
现有技术还公开了各种2-二烷氨基嘧啶酮衍生物可以用于控制植物病害(参见JP-A 190 670-1989和JP-A 112 566-1988)。然而,如果以低剂量使用这些先前已知的化合物,其活性总是不能完全令人满意。
目前发现式(Ⅰ)的嘧啶酮衍生物非常适用于控制不希望的微生物
其中
R1表示烷氧基,
R2表示氢或烷基,
R3表示烷基或苯基,以及
R4表示任意取代的芳基、任意取代的杂芳基或任意取代的杂芳烷基。
出人意料地,本发明化合物比具有同样作用的结构上最相似的现有化合物显示出明显更好的杀微生物活性。
式(Ⅰ)提供了可用于本发明的嘧啶酮衍生物的一般定义。R1优选表示具有1-6个碳原子的直链或支链烷氧基。R2优选表示氢或具有1-6个碳原子的直链或支链烷基。R3优选表示具有1-6个碳原子的直链或支链烷基或表示苯基。R4优选表示具有6-10个碳原子的芳基,其中这些基团中的每一个可以被相同或不同的选自下列一组的基团一至三取代:卤素、硝基、氰基、具有1-6个碳原子的烷基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷基、具有1-6个碳原子的烷氧基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷氧基、具有3-8个碳原子的环烷基、苯基和苯氧基,或者R4优选表示具有1-3个杂原子如氮、硫和/或氧的5-或6-元杂芳基,其中每个杂环基可以被相同或不同的选自下列一组的基团一至三取代:卤素、硝基、烷氧基部分具有1-6个碳原子的烷氧羰基、氰基、具有1-6个碳原子的烷基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷基、具有1-6个碳原子的烷氧基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷氧基、具有3-8个碳原子的环烷基、苯基和苯氧基,或者R4优选表示烷基部分具有1-6个碳原子并且杂芳基部分具有1-3个杂原子如氮、硫和/或氧的5-或6-元杂芳烷基,其中每个杂环基可以被相同或不同的选自下列一组的基团一至三取代:卤素、硝基、烷氧基部分具有1-6个碳原子的烷氧羰基、氰基、具有1-6个碳原子的烷基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷基、具有1-6个碳原子的烷氧基、具有1-6个碳原子和1-5个相同或不同的卤原子的卤代烷氧基、具有3-8个碳原子的环烷基、苯基和苯氧基。
特别优选的是如下的式(Ⅰ)嘧啶酮衍生物,其中R1表示具有1-4个碳原子的直链或支链烷氧基,R2表示氢或具有1-4个碳原子的直链或支链烷基,R3表示具有1-4个碳原子的直链或支链烷基或苯基,以及R4表示苯基或萘基,它们各自可以被相同或不同的选自下列一组的基团一至三取代:氟、氯、溴、硝基、氰基、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基、具有1-4个碳原子的烷氧基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基、具有3-7个碳原子的环烷基、苯基和苯氧基,或者R4表示具有1-3个杂原子如氮、硫和/或氧的5-至6-元杂芳基,其中每个杂环基可以被相同或不同的选自下列一组的基团一至三取代:氟、氯、溴、硝基、烷氧基部分具有1-4个碳原子的烷氧羰基、氰基、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基、具有1-4个碳原子的烷氧基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基、具有3-7个碳原子的环烷基、苯基和苯氧基,或者R4优选表示烷基部分具有1-4个碳原子并且杂芳基部分具有1-3个杂原子如氮、硫和/或氧的5-或6-元杂芳烷基,其中每个杂环基可以被相同或不同的选自下列一组的基团一至三取代:氟、氯、溴、硝氧基部分具有1-4个碳原子的烷氧羰基、氰基、具有1-4个碳原子的烷基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷基、具有1-4个碳原子的烷氧基、具有1-4个碳原子和1-5个氟、氯和/或溴原子的卤代烷氧基、具有3-7个碳原子的环烷基、苯基和苯氧基。R1表示甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、促丁氧基或叔丁氧基,R2表示氢、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基,R3表示甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基或苯基,以及R4表示苯基或萘基,它们各自可以被相同或不同的选自下列一组的基团一一至三取代:氟、氯、溴、硝基、氰基、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氯甲基、氯二氟甲基、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、叔丁氧基、三氟甲氧基、氯二氟甲氧基、三氯甲氧基、环丙基、环戊基、环己基、环庚基、苯基和苯氧基,或者R4表示噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,4-三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基,这些杂环基中的每一个可以被相同或不同的选自下列一组的基团-至三取代:氟、氯、溴、硝基、甲氧羰基、乙氧羰基、氰基、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氯甲基、氯二氟甲基、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、叔丁氧基、三氟甲氧基、氯二氟甲氧基、三氯甲氧基、环丙基、环戊基、环己基、环庚基、苯基和苯氧基,或者R4表示式-A-R5基团,其中A表示具有1-4个碳原子的直链或支链亚烷基,并且R5表示噻吩基、呋喃基、吡咯基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,4-三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基,这些杂环基中的每一个可以被相同或不同的选自下列一组的基团一至三取代:氟、氯、溴、硝基、甲氧羰基、乙氧羰基、氰基、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、三氯甲基、氯二氟甲基、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、叔丁氧基、三氟甲氧基、氯二氟甲氧基、三氯甲氧基、环丙基、环戊基、环己基、环庚基、苯基和苯氧基。
上述取代基的定义可以彼此结合。此外,逐个定义是累赘和多余的。
在某些情况下(参见EP-A 0 636 615),可以按本发明使用的式(Ⅰ)的嘧啶酮衍生物是已知的。
R1表示烷氧基,
R2表示氢或烷基,
R3表示烷基或苯基,和
可以通过下述方法制备式(Ⅰa)的嘧啶酮类衍生物。如果需要,在酸结合剂存在下,以及如果需要,在稀释剂存在下,将式(Ⅱ)的甲硫基嘧啶酮类
其中
R1、R2和R3如上所定义,与式(Ⅲ)的胺类反应H2N-R6 (Ⅲ)其中R6如上所定义。
可以以同样的方式制备已知的式(Ⅰ)嘧啶酮类衍生物。
式(Ⅰa)提供了新嘧啶酮衍生物的一般定义。优选的是如下的式(Ⅰa)化合物,其中R1、R2和R3具有如上述优选基团的定义,并且R6如上所定义。
特别优选的是如下的式(Ⅰa)化合物,其中R1、R2和R3具有如上述特别优选基团的定义,并且R6如上所定义。
更特别优选的是如下的式(Ⅰa)化合物,其中R1、R2和R3具有如上述更特别优选基团的定义,并且R6如上所定义。
如果用2-甲硫基-3-甲基-6-甲氧基嘧啶-4-酮和2-甲氧羰基-3-氨基-4-甲基噻吩作原料,可以通过下式的反应流程对本发明方法的反应进程进行说明:
式(Ⅱ)提供了用作实施本发明方法所需原料的甲硫基嘧啶酮类的一般定义。在该式中,R1、R2和R3优选具有那些业已提到的这些基团的优选定义。
式(Ⅱ)的甲硫基嘧啶酮类是已知的或者可以通过已知方法制备(参见EP-A 0 636 615)。
式(Ⅲ)提供了用作实施本发明方法所需反应组分的胺的一般定义。在该式中,R6具有那些业已提到的这些基团的优选定义。
式(Ⅲ)的胺是已知的或者可以通过已知方法制备(参见EP-A 0 636615)。
在实施本发明的方法时,还可以用式(Ⅳ)的甲酰基取代的胺代替式(Ⅲ)的胺其中R6如上所定义。
式(Ⅳ)的甲酰基取代的胺也是已知的或者可以按照已知的方法制备。
本发明的方法优选在酸结合剂存在下进行。合适的酸结合剂是所有常规的无机和有机碱。优选使用碱土金属或碱金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、乙酸钠、乙酸钾、醋酸钙、碳酸钠、碳酸钾、碳酸氢钾或碳酸氢钠,此外还有铵化合物,例如氢氧化铵、乙酸铵或碳酸铵,以及叔胺,例如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)或二氮杂双环十一烯(DBU)。
实施本发明方法的合适的稀释剂是所有常规的惰性有机溶剂。优选使用任意卤化的脂族、脂环族或芳香族烃类,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚,例如乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或茴香醚;酮类,例如丙酮、丁酮、甲基异丁基酮或环己酮;腈,例如乙腈、丙腈、正-或异丁腈或者苄腈;酰胺,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜,例如二甲基亚砜;砜,例如环丁砜,或者胺类例如吡啶。
在实施本发明的方法时,反应温度可以在较宽的范围内变化。一般来说,该反应可以在0℃至150℃的温度范围内进行,优选20℃至140℃。
本发明的方法通常在大气压下进行。但是,也可以在升高或降低的压力下进行。
在实施本发明的方法时,通常以等摩尔量使用式(Ⅱ)的甲硫基嘧啶酮类和式(Ⅲ)的胺类。但是也可以使用过量的两种成分之一。后处理采用常规方法进行。一般来说,将反应混合物用水稀释,然后用仅与水少量混溶的有机溶剂萃取,将合并的有机相干燥并减压浓缩。可以采用现有的常规方法例如色谱或重结晶法去除产物中的任何杂质。
本发明的化合物具有潜在的杀微生物活性并且可以在作物保护和原料保护中用于控制不希望的微生物,例如真菌和细菌。该化合物适用于直接控制不希望的微生物以及在植物中产生抵御不希望微生物侵袭的抗性。
作物保护中的杀真菌剂被用来防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌类。
在作物保护中的杀菌剂被用来防治假单孢菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科。
上面列出的某些病原真菌和细菌病害以属名给出,可以提到的有例如下列,但决不限于此:黄单孢菌属,如田野黄单孢菌稻变种(Xanthomonas campestris pv.oryzae);假单孢菌属,如丁香假单孢菌黄瓜角斑病变种(Pseudomonas syringae pv.lachrymans);欧文氏杆菌属,如解淀粉欧文氏杆菌(Erwinia amylovora);腐霉属,如终极腐霉(Pythium ultimum);疫霉属,如蔓延疫霉(Phytophthora infestans);假霜霉属,如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);单轴霉属,如葡萄生单轴霉(Plasmopara viticola);盘梗霉属,如莴苣盘梗霉(Bremia lactucae);霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);白粉菌属,如禾白粉菌(Erysiphe graminis);单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);黑星菌属,如苹果黑星菌(Venturia inaequalis);核腔菌属,如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);柄锈属,如隐匿柄锈菌(Puccinia recondita);核盘菌属,如油菜核盘菌(Sclerotinia sclerotiorum);腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);梨孢菌属,如稻梨孢菌(Pyricularia oryzae);镰孢属,如大刀镰孢(Fusarium culmorum);葡萄孢属,如灰色葡萄孢(Botrytis cinerea);壳针孢属,如颖枯壳针孢(Septoria nodorum);小球腔菌属,如颖枯病小球腔菌(Leptosphaeria nodorum);尾孢属,如变灰尾孢菌(Cercospora canescens);链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和假小尾孢菌属,如麦类眼斑病菌(Pseudocercosporallaherpotrichoides)。
在防治植物病害所需浓度下,活性化合物的良好作物安全性,使活性化合物可以处理植物的地上部分、无性繁殖原种和种子以及土壤。
本发明的活性化合物可以特别成功地用于禾谷类中的病害例如白粉菌种类的病害,或防治葡萄栽培、果树种植和园艺上的病害,如防治单轴霉或黑星菌种类的病害,或者防治稻中的病害,如防治梨孢菌种类病害。
本发明的活性化合物还适用于增加收成。此外,它们具有降低的毒性和良好的作物安全性。
另外,本发明的活性化合物具有很强的使植物产生抗性的作用。因此它们适用于使植物产生抵御不希望微生物的抗性。
在本文中,产生抗性的物质应理解为是这样的物质,一方面,当它们直接作用于不希望的微生物时仅仅显示出低活性,但是当它们与不希望的微生物接触时,它们能够刺激植物如所处理植物的防御系统,对这些微生物产生更大的抗性。
在本发明中,不希望的微生物应理解为致病真菌、细菌和病毒。因此本发明的物质可以用于在某些时期使受到上述有害致病微生物侵袭后的植物产生抗性。产生抗性的时间阶段通常为用活性化合物处理植物后的1-10天,优选1-7天。
在材料保护方面,本发明化合物可以用于保护工业材料以防治被不希望的微生物感染和破坏。
本发明所述的工业材料是指为工业应用所制造的无生命的物质。例如,可以用本发明活性化合物保护以防止微生物引起的变化或破坏的工业物质可以是粘合剂、胶料、纸和板、织物、皮革、木材、染料和塑料制品、冷却润滑油(cooling lubricants)和其他可以被微生物感染或破坏的材料。会受到微生物增殖损坏的制造厂的某些部分例如冷水循环系统也在本发明的保护材料范围之内。本发明中可以提及的工业材料优选为粘合剂、胶料、纸和板、织物、皮革、木材、染料和塑料制品、冷却润滑油和热传递液体,特别优选木材。
可以提及的可降解或改变工业材料的微生物是例如细菌、真菌、藻类和粘质物或生物体。本发明的活性物质优选用于抗真菌,特别是霉菌、使木材变色和破坏木材的真菌(担子菌纲Basidiomycetes)以及抗粘质物生物体和藻类。
可以提及的有例如以下属的微生物:链格孢属,例如纤细链格孢(Alternaria tenuis),曲霉属,例如黑色曲霉(Aspergillus niger),毛壳霉属,例如球毛壳霉(Chaetomium globosum),粉孢革菌属,例如单纯粉孢革菌(Coniophora puetana),香菇属,例如Lentinus tigrinus,青霉属,例如灰绿青霉(Penicilium glaucum),多孔菌属,例如变色多孔菌(Polyporus versicolor),短柄霉属属,例如出芽短柄霉(Aureobasidium pullulars),Sclerophoma,例如Sclerophoma pityophila,木霉属,例如绿色木霉(Trichoderma viride),杆菌属,例如大肠杆菌(Escherichia coli),假单孢菌属,例如铜绿假单孢菌(Pseudomonas aeruginosa),葡萄球菌属,例如金黄色葡萄球菌(Staphylococcus aureus)。
根据其具体的物理和/或化学特性,活性化合物可以转化成常规剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂、聚合物和用于种子的包衣组合物的细微胶囊、以及ULV冷和热雾剂。
这些型剂可以用已知的方式生产,例如,将活性化合物与填充剂(即液体溶剂、加压液化气体)混合,和/或与固体载体混合,并任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)。用水作填充剂的情况下,也可以用有机溶剂作助溶剂。作为液体溶剂,适合的主要有:芳族化合物,如二甲苯、甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如矿物油馏份,醇类,如丁醇或甘醇以及其醚和酯,酮类,如丙酮、乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲亚砜,以及水;液化气填充剂或载体是指环境温度和大气压力下是气体的液体,例如气雾抛射剂,如丁烷、丙烷、氮气和二氧化碳;固体载体适合的有:磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的固体载体适合的有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;乳化剂和/或起泡剂适合的有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;分散剂适合的有:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它的粘合剂可以是矿物油和植物油。
也可能使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。
当用于植物保护时,本发明的活性化合物可以以其本身或以其制剂形式,或作为与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂的混合物的形式使用,以例如扩大作用谱,或为防止抗性的逐步建立。在许多情况下,可以获得增效作用,即该混合物的活性超出单个组分的活性。适合用于混合物的组分是例如下列化合物:杀真菌剂:
aldimorph、氨丙磷酸、andoprim、敌菌灵、戊环唑、azovystrobin、苯霜灵、碘萎灵、苯菌灵、benzamacil、benzamacil-isobutyl、氨丙酸钾、bialaphos、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、石硫合剂、capscmycin、敌菌丹、克菌丹、多菌灵、萎锈灵、甲基克杀螨、灭瘟唑、chlorfenazole、地茂散、氯化苦、百菌清、乙菌利、硫杂灵、霜脲氰、环唑醇、cyprodinil、酯菌胺、debacarb、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、烯唑醇M、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二烷胍、腙菌酮、克瘟散、环氧唑(epoxyconazole)、乙环唑、乙嘧吩、土菌灵、famoxadon、咪菌腈、氯苯嘧啶醇、苯氰唑、一甲呋萎灵、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、flumetover、氟氯菌核利、fluquinconazole、调嘧醇、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、乙磷钠、四氯苯酞、麦穗宁、呋霜灵、furametpyr、二甲呋酰苯胺、farcabonil、呋菌唑、顺式呋菌唑、拌种胺、谷种定、六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛、双胍辛烷苯基磺酸盐、双胍辛醋酸盐、iodocarb、ipconazole、异稻瘟净、异菌脲、irumamycin、稻瘟灵、isovaledione、春日霉素、kresoxim-methyl、铜制剂如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、双代混剂、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、metconazole、磺菌威、担菌胺、代森联、氯苯咯菌胺、噻菌胺、腈菌唑、甲菌利、福美镍、异丙消、氟苯嘧啶醇、甲呋酰胺、噁酰胺、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin、多效唑、稻瘟酯、戊菌唑、戊菌隆、稻病磷、匹马菌素、哌啶宁、多氧霉素、polyoxorim、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、propanosine-sodium、丙环唑、甲基代森锌、定菌磷、啶斑肟、pyrimethanil、咯喹酮、氯吡呋醚、quinconazole、五氯硝基苯、quinoyfen、硫磺和硫制剂、戊唑醇、酞枯酸、四氯硝基苯、调环烯、氟醚唑、噻菌灵、噻菌腈、thifluzamide、甲基托布津、福美双、tioxymid、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、triazbutil、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、triticonazole、烯效唑、稻纹散、乙烯菌核利、烯霜苄唑、zarilamide、代森锌、福美锌,以及Dagger G,OK-8705,OK-8801,α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,{2-甲基-1-[[[1-(4-甲基苯基)乙基]氨基]羰基]丙基]氨基甲酸异丙酯,1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-0-(苯甲基)肟,1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,1-[(二碘甲基)磺酰基]-4-甲基苯,1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]甲基]-1H-咪唑,1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]甲基]-1H-1,2,4-三唑,1-[1-[2-[(2,4-二氯苯基)-甲氧基]苯基]乙烯基]-1H-咪唑,1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇(pyrrolidinole),2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺,2,2-二氯-N-[1-(4-氯苯基)乙基]-1-乙基-3-甲基环丙烷甲酰胺,2,6-二氯-5-(甲硫基)-4-嘧啶硫代氰酸酯,2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺,2,6-二氯-N-[[4-(三氟甲基)苯基]甲基]苯甲酰胺,2-(2,3,3-三碘-2-丙烯基)-2H-四唑,2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,2-[[6-去氧-4-0-(4-0-甲基-β-D-吡喃葡糖基)-α-D-吡喃葡糖基]氨基-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-甲腈,2-氨基丁烷,2-溴-2-(溴甲基)戊二烯二腈,2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,2-氯-N-(2,6-二甲基苯基)-N-(异硫代氰酰甲基)乙酰胺,2-苯基苯酚(OPP),3,4-二氯-1-[4-(二氟甲氧基)苯基]-1H-吡咯-2,5-二酮,3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)氧]甲基]苯甲酰胺,3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]吡啶,4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,4-甲基四唑并[1,5-a]喹唑啉-5(4H)-酮,8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二噁螺[4,5]癸-2-甲胺,硫酸8-羟基喹啉,9H-呫吨-2-[(苯基氨基)羰基]-9-酰肼,二-(1-甲基乙基)-3-甲基-4-[3-甲基苯甲酰基)氧]-2,5-噻吩二甲酸,顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇,顺-4-[3-[4-(1,1-二甲基丙基)苯基-2-甲基丙基]-2,6-二甲基吗啉盐酸盐,[(4-氯苯基)偶氮]氰基乙酸乙酯,碳酸氢钾,甲烷四硫醇钠盐,1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯,N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,N-(氯乙酰基)-N-(2,6-二甲苯基)-DL-丙氨酸甲酯,N-(2,3-二氯-4-羟基苯基)-1-甲基环己烷甲酰胺,N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)乙酰胺,N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)乙酰胺,N-(2-氯-4-硝基苯基)-4-甲基-3-硝基苯磺酰胺,N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)乙酰胺,N-(6-甲氧基)-3-吡啶基-环丙烷甲酰胺,N-[2,2,2-三氯-1-[(氯乙酰基)氨基]乙基]苯甲酰胺,N-[3-氯-4,5-二-(2-丙炔氧基)苯基]-N’-甲氧基-甲烷亚胺酰胺,N-甲酰基-N-羟基-DL-丙氨酸钠盐,[2-(二丙基氨基)-2-氧乙基]-乙基硫代氨基磷酸0,0-二乙基酯,苯基丙基硫代氨基磷酸O-甲基S-苯基酯,1,2,3-苯并噻二唑-7-硫代甲酸S-甲酯,螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮。杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿维菌素(avermectin)、AZ 60541、苦楝素、乙基谷硫磷、谷硫磷、三唑锡、苏芸金杆菌、4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-1H-吡咯-3-腈、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、除线威、氯氧磷、chlorfenapgr、毒虫畏、定虫隆、氯甲硫磷、N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙基亚胺酰胺、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、溴氰菊酯、甲基内吸磷、内吸磷、异吸磷Ⅱ、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、氟虫腈、氟啶胺、fluazuron、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、六六六、庚虫磷、氟铃脲、噻螨酮、吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、lufenuron、马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、二溴磷、NC 184、nitenpyram、氧乐果、草肟威、砜吸硫磷、异砜磷、对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊、哒螨酮、pyrimidifen、蚊蝇醚、喹硫磷、水杨硫磷、硫线磷、氟硅菊酯、治螟磷、甲丙硫磷、虫酰肼、吡螨胺、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafenox、thiamethoxam、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、trimethacarb、完灭硫磷、二甲威、二甲苯威、zetamethrin。
如果需要,本发明活性化合物也可与其它已知活性化合物如除草剂、或与化肥和生长促进物质混合。
活性化合物可以以其原样或以其制剂或由其制备的使用形式使用,所述的制备使用形式有例如可直接使用溶液、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉剂和颗粒剂。它们以常规方法使用,例如浇泼、喷雾、弥雾、撒施、喷粉、起泡、涂刷等等。此外可用超低容量方法使用化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可处理植物的种子。
当使用本发明的活性化合物控制微生物时,其施用比例可在大范围内变化,这取决于施用形式。处理植物部分时,活性化合物的施用比例通常在0.1和10000,优选在10和1000克/公顷之间。处理种子时,活性化合物的施用比例通常为每公斤种子0.001至50克,优选0.01至10克。处理土壤时,活性化合物的施用比例通常在0.1至10000克/公顷之间,优选在1至5000克/公顷之间。
保护工业材料用的组合物通常含有1-95%、优选10-75%的活性化合物。
本发明活性化合物的使用浓度取决于所控制微生物的种类和感染情况以及被保护的材料的组成。最佳施用比例可以通过一系列实验来测定。一般来说,根据被保护的材料,其使用浓度在0.001-5%(重量)的范围内,优选0.05-1.0%(重量)。
如果需要,还可以通过加入其它具有抗微生物作用的化合物、杀真菌剂、杀细菌剂、除草剂、杀虫剂或可增加活性谱或者获得特定效果例如抵御昆虫的额外保护作用的活性化合物,使本发明用于材料保护的活性化合物、或由其制备的组合物、浓缩物或其非常普通制剂的活性或者活性谱增加。这些混合物可以比本发明的化合物具有更宽的活性谱。
通过以下实施例说明本发明化合物的制备与应用。制备实施例实施例1
向2.74克(16毫摩尔)2-甲氧羰基-3-氨基-4-甲基噻吩在10毫升二甲基甲酰胺中的溶液中加入0.6克氢化钠(95%)。在室温搅拌该混合物10分钟,加入3.73克(毫摩尔)3-甲基-2-甲硫基-6-甲氧基嘧啶-4-酮。
在120℃搅拌所得混合物8小时。向反应混合物中加入冰水,然后用乙酸乙酯萃取反应混合物。合并的有机相依次用水和饱和氯化钠水溶液洗涤。有机相用无水硫酸钠干燥并减压浓缩。用己烷处理使残余物(4.0克)结晶。滤出结晶的固体并用己烷洗涤,得到1.43克上式所示的化合物。浓缩有机滤液,剩余的产物经硅胶柱色谱纯化,用己烷/丙酮=2∶1洗脱。浓缩洗脱液后,得到0.12克上式化合物,为固体,熔点180-182℃。该化合物的总产量为1.55克(=理论值的31.3%)。
向1.45克(8毫摩尔)N-甲酰基-2,4-二甲氧基苯胺在20毫升二甲基甲酰胺中的溶液中加入0.5克氢化钠(95%)。在室温搅拌该混合物10分钟,加入2.14克(10毫摩尔)2-甲硫基-3-甲基-6-异丙氧基嘧啶-4-酮。在100℃搅拌反应混合物7小时。向反应混合物中加入冰水,然后用乙酸乙酯萃取反应混合物。合并的有机相依次用水和饱和氯化钠水溶液洗涤。有机相用无水硫酸钠干燥并减压浓缩。残余物(1.5克)经硅胶柱色谱纯化,用己烷/丙酮=2∶1洗脱。浓缩洗脱液后,得到0.70克(理论值的27.4%)上式化合物,为结晶固体,熔点140-142℃。
向10.0克(58毫摩尔)3-甲基-2-甲硫基-6-羟基嘧啶-4-酮在100毫升二甲基甲酰胺中的溶液中加入4.4克(36毫摩尔)碳酸钾。在室温下搅拌该混合物,同时滴加7.5克(61毫摩尔)异丙基溴。在60℃搅拌该混合物3小时,向其中加入水。然后用乙酸乙酯萃取所得混合物。合并的有机相依次用水和饱和氯化钠水溶液洗涤,然后用无水硫酸钠干燥。减压浓缩有机相。得到3.9克(理论值的31.4%)3-甲基-2-甲硫基-6-异丙基嘧啶-4-酮,为固体产物,熔点79-80℃。
实施例30
向13.57克(58毫摩尔)2-甲硫基-3-苯基-5-甲基-6-羟基嘧啶-4-酮在100毫升二甲基甲酰胺中的溶液中加入4.4克(36毫摩尔)碳酸钾。在室温搅拌该混合物,同时滴加8.7克(61毫摩尔)甲基碘。在60℃搅拌该混合物3小时,向其中加入水,用乙酸乙酯萃取所得混合物。合并的有机相依次用水和饱和氯化钠水溶液洗涤,然后用无水硫酸钠干燥。减压浓缩有机相,残余物(12.5克)经硅胶柱色谱纯化,用己烷/丙酮=2∶1洗脱。减压浓缩洗脱物后,得到2.50克(理论值的17.4%)2-甲硫基-3-苯基-5-甲基-6-甲氧基嘧啶-4-酮,为固体产物,熔点149-152℃。
还可以按照实施例29和30所述方法制备下表2所示的式(Ⅱ)化合物。表2 还可以按照上述方法制备下表中所示的化合物。表3 表3(续)表3(续)表3(续)表3(续)表3(续)表3(续)
表3(续)表3(续)在上面表3中,基团Q1-Q9具有以下含义: 表4
用途实施例
实施例序号 | R1 | R2 | R3 | R4 | 熔点[℃] |
101 | -OCH3 | H | -C2H5 | Q1 | |
102 | -OCH3 | H | -C2H5 | Q2 | |
103 | -OCH3 | H | -C2H5 | Q3 | |
104 | -OCH3 | H | -C2H5 | Q4 | |
105 | -OCH3 | H | -C2H5 | Q5 | |
106 | -OCH3 | H | -C2H5 | Q6 | |
107 | -OCH3 | H | -C2H5 | Q7 | |
108 | -OCH3 | H | -C2H5 | Q8 | |
109 | -OCH3 | H | -C2H5 | Q9 | |
110 | -OCH3 | H | -C3H7-n | Q1 | |
111 | -OCH3 | H | -C3H7-n | Q2 | |
112 | -OCH3 | H | -C3H7-n | Q3 | |
113 | -OCH3 | H | -C3H7-n | Q4 | |
114 | -OCH3 | H | -C3H7-n | Q5 | |
115 | -OCH3 | H | -C3H7-n | Q6 | |
116 | -OCH3 | H | -C3H7-n | Q7 | |
117 | -OCH3 | H | -C3H7-n | Q8 | |
118 | -OCH3 | H | -C3H7-i | Q1 | |
119 | -OCH3 | H | -C3H7-i | Q2 | |
120 | -OCH3 | H | -C3H7-i | Q3 | |
121 | -OCH3 | H | -C3H7-i | Q4 | |
122 | -OCH3 | H | -C3H7-i | Q5 | |
123 | -OCH3 | H | -C3H7-i | Q6 | |
124 | -OCH3 | H | -C3H7-i | Q7 | |
125 | -OCH3 | H | -C3H7-i | Q8 | |
126 | -OCH3 | H | -C4H9-n | Q1 | |
127 | -OCH3 | H | -C4H9-n | Q2 |
实施例序号 | R1 | R3 | 熔点[℃] | |
143 | -OCH3 | H | -C2H5 | |
144 | -OCH3 | H | -C3H7-n | |
145 | -OCH3 | H | C3H7-i | |
146 | -OCH3 | H | -CH3 |
实施例A白粉菌属实验(大麦)/引发抗性溶剂: 50份重量的N,N-二甲基甲酰胺乳化剂:1.17份重量的烷芳基聚乙二醇醚
制备活性化合物的合适制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并将该乳油用水稀释至所需浓度。
测试产生抗性活性时,将幼株大麦用所述施用比例的活性化合物制剂喷雾。处理4天后,将植株用禾白粉菌大麦亚种的芽孢水悬浮液接种。然后将该植物置于相对湿度70%、18℃的温室中。
接种7天后进行评价。0%是指对照的有效率,100%是指没有发现病害。
Claims (6)
2.控制不希望微生物的方法,其特征在于将权利要求1的式(Ⅰ)嘧啶酮类衍生物施用在所述微生物或其生存环境中。
4.权利要求3的式(Ⅰa)嘧啶酮类衍生物的制备方法,其特征在于:如果需要,在酸结合剂存在下,以及如果需要,在稀释剂存在下,将式Ⅱ的甲硫基嘧啶酮
其中
R1、R2和R3如上所定义,与式(Ⅲ)的胺反应H2N-R6(Ⅲ)
其中
R6如上所定义。
5.杀微生物组合物,其特征在于它含有至少一种权利要求3的式(Ⅰa)嘧啶酮类衍生物与增量剂和/或表面活性剂混合物。
6.制备杀微生物组合物的方法,其特征在于权利要求3的式(Ⅰa)嘧啶酮类衍生物与增量剂和/或表面活性剂混合。
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PCT/EP2000/010623 WO2001034576A2 (en) | 1999-11-09 | 2000-10-27 | Use of pyrimidinone derivatives for controlling undesired microorganisms |
AU16977/01A AU1697701A (en) | 1999-11-09 | 2000-10-27 | Use of pyrimidinone derivatives for controlling undesired microorganisms |
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