CN1671698A - 经4-三氟甲基吡唑取代的吡啶和嘧啶类化合物 - Google Patents
经4-三氟甲基吡唑取代的吡啶和嘧啶类化合物 Download PDFInfo
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- CN1671698A CN1671698A CNA038175975A CN03817597A CN1671698A CN 1671698 A CN1671698 A CN 1671698A CN A038175975 A CNA038175975 A CN A038175975A CN 03817597 A CN03817597 A CN 03817597A CN 1671698 A CN1671698 A CN 1671698A
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- -1 4-trifluoromethylpyrazolyl Chemical group 0.000 title claims abstract description 62
- 150000003230 pyrimidines Chemical class 0.000 title abstract description 6
- 150000003222 pyridines Chemical class 0.000 title 1
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
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- 150000001875 compounds Chemical class 0.000 claims description 80
- 239000000203 mixture Substances 0.000 claims description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
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- 238000000034 method Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
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- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 claims description 4
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- 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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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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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
- C07D405/14—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 three or more hetero rings
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Abstract
本发明描述了式(I)的经4-三氟甲基吡唑基取代
的吡啶和嘧啶类化合物以及将其用作除草剂。式(I)中,
R1、
R2、
R3和
R4代表各种基团,A为芳族和杂
芳族基团,并且Z为氮或碳原子。
Description
本发明涉及除草剂技术领域,尤其是用于选择性控制有用作物中的阔叶和禾本科杂草的杂芳基吡唑类除草剂。
从多种出版物中已知某些经唑基(如吡唑基、咪唑基和三唑基)取代的吡啶和嘧啶化合物具有除草性质。例如WO 99/28301公开了2位上具有唑基和6位上通过一个碳原子连有芳族或杂芳族基团的吡啶和嘧啶类化合物。WO 98/40379公开了2位具有唑基和6位通过一个氧、氮或硫的原子连有芳族或杂芳族基团的吡啶和嘧啶类化合物。2位上的唑基可由多种基团取代。这些出版物公开了多种适合吡唑基的取代基,均在3位上。EP-A 1 101 764公开了2位上经3-三氟甲基-1-吡唑基取代的除草的吡啶类化合物。
然而已经在上述文献中公开的化合物不断显示出不足的除草活性。因此本发明的任务是提供一种具有比现有化合物改良的除草特性的除草有效的化合物。
现已发现某些经4-三氟甲基吡唑取代的吡啶和嘧啶类化合物特别适用于除草剂。因此,本发明的主题是式(I)的化合物,其N-氧化物及其盐,
其中基团和符号如下定义:
Z为N或CR8;
Y为Y1至Y7的基团:
R1和R2分别独立地为氢、卤素、氰基、异氰基、OH、COOR10、COR10、CH2OH、CH2SH、CH2NH2、NO2、CSNH2、CONH2、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基、(C1-C2)-烷氧基-(C1-C2)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C4)-烯氧基、(C3-C4)-炔氧基、(C1-C2)-烷硫基-(C1-C2)-烷基、S(O)nR9、(C1-C2)-烷基磺酰基-(C1-C2)-烷基、氨基、(C1-C4)-烷基氨基、(C1-C3)-烷基羰基氨基、(C1-C4)-烷基磺酰基氨基或二-(C1-C4)-烷基氨基;
R3和R4分别独立地为氢、卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基或卤代-(C1-C4)-烷氧基;
R5为卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基、卤代-(C1-C4)-烷硫基、(C3-C5)-环烷基、卤代-(C3-C5)-环烷基、SF5、S(O)nR9、(C2-C4)-烯基或(C2-C4)-炔基;
R6为氢、卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基或S(O)nR9;
R7为(C1-C4)-烷基;
R8为氢、卤素、氰基、NO2、(C1-C4)-烷基、(C1-C4)-烷氧基、羟基、氨基、(C1-C4)-烷基氨基、(C1-C3)-烷基羰基氨基、(C1-C4)-烷基磺酰基氨基、二-(C1-C4)-烷基氨基或S(O)nR9;
R9为氢、(C1-C4)-烷基或卤代-(C1-C4)-烷基;
R10为氢或(C1-C4)-烷基;
n为0,1或2。
在式(I)和随后所有化学式中,烷基、烯基和炔基可以为具有多于两个或三个碳原子的直链或支链。烷基为甲基、乙基、正-或异-丙基、正-、异-、叔-或2-丁基。烯基相应地为乙烯基、1-丙烯基、2-丙烯基和各种丁烯基的异构体。炔基为乙炔基、1-丙炔基、2-丙炔基和各种丁炔基的异构体。复合定义中的术语,如烷氧基、烯氧基、炔氧基和烷硫基应类似地理解。因此例如炔氧基为HC≡CCH2O、CH3C≡CCH2O和CH3C≡CCH2CH2O。
环烷基为环丙基、环丁基、环戊基或环己基。
在经双重取代的氨基中,如二烷基氨基,这两个取代基可相同或不同。
卤素为氟、氯、溴或碘。卤烷基为烷基部分或完全由卤素,优选由氟、氯和/或溴,尤其是由氟或氯取代的,例如CF3、CHF2、CH2F、CF3CF2、CH2FCHCl、CCl3、CHCl2、CH2CH2Cl;卤烷氧基为例如OCF3、OCHF2、OCH2F、CF3CF2O、OCH2CF3和OCH2CH2Cl;相应地适用于其它经卤素取代的基团。
根据取代基的性质和连接方式,式(I)化合物可以以立体异构体存在。例如若有双键,则可产生非对映异构体。例如若有一个或多个不对称碳原子,则可产生对映异构体和非对映异构体。立体异构体可采用常规分离方法从制备产生的混合物中获得,例如采用色谱分离技术。同样的,立体异构体可利用立体选择性反应和光学活性初始物质和/或助剂选择性地加以制备。本发明还涉及式(I)所包括而无特别定义的所有的立体异构体及其混合物。
式(I)化合物通常可生成N-氧化物的形式。N-氧化物可根据本领域技术人员熟知的方法采用将氧化试剂如过酸、过氧化氢和过硼酸钠反应制得。这类方法描述于例如T.L.Gilchrist,ComprehensiveOrganic Synthesis,第7卷,第748-750页,S.V.Ley,Ed.,PergamonPress中。
式(I)化合物通常通过加入下列化合物形成盐
a)酸,例如氯化氢、溴化氢、硝酸、磷酸、硫酸、乙酸、草酸或
b)碱,例如吡啶、氨、三乙胺、碳酸钠、碳酸钾、氢氧化钠、氢氧化钾。
本发明化合物优选的实施方式始终包括所述N-氧化物和盐,除非下面另有说明。
尤其重要的是其中Y为Y1至Y6基团的式(I)化合物。
已发现有利的式(I)化合物包括这样的化合物,其中R1和R2分别为氢、卤素、氰基、OH、CHO、乙烯基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、乙烯基或(C1-C4)-烷氧基,并且其它取代基和符号均如上所定义。
同样优选的是其中R3和R4分别独立地为氢、卤素、甲基或甲氧基,并且其它取代基和符号均如上所定义的式(I)化合物。
优选的式(I)化合物是其中
R1为氢、卤素、氰基、CHO、甲氧基、甲基或乙基,并且
R2为氢、OH、甲基、乙基、甲氧基或乙氧基,并且其它取代基和符号均如上所定义的化合物。
同样优选的是其中R3和R4分别为氢或甲基,并且其它取代基和符号均如上所定义的式(I)化合物。
尤其优选的是其中R8为氢、卤素或(C1-C4)-烷基,并且其它取代基和符号均如上所定义。
同样尤其优选的是其中R5为卤素、氰基、卤代-(C1-C4)-烷基、卤代-(C1-C4)-烷氧基或卤代-(C1-C4)-烷硫基,并且其它取代基和符号均如上所定义。
另外尤其优选的是其中R6为氢,并且其它取代基和符号均如上所定义。
下面所有式中的取代基和符号具有如式(I)所述的同样定义,除非另有说明。
本发明的化合物例如可通过如下示意图所给出的反应路径加以制备:
根据图示1将其中E1为离去基团如卤素、甲基磺酰基或甲苯磺酰基的式(IIa)化合物在碱催化下与式(III)化合物反应。该反应是本领域技术人员已知的。
图示1:
其中E1为卤素的式(IIa)化合物例如可根据图示2在碱催化下将式(IV)化合物与式(V)的吡唑化合物反应制得。在该反应中,可形成局部异构体(regioisomers)(IIa)和(IIb),它们可采用例如色谱精处理进行分离。该反应是本领域技术人员已知的。
图示2:
根据图示3,其中E1为甲基磺酰基的式(IIa)化合物可通过从式(IIc)化合物采用间-氯过苯甲酸(MCPA)或Oxone氧化反应制得。该反应是本领域技术人员已知的,例如通过J.March,AdvancedOrganic Chemistry,John Wiley,New York,1992,第4版,第1201-1203页。
图示3:
根据图示4,式(IIb)化合物可通过将式(VI)化合物与式(V)的吡唑化合物进行碱催化反应加以制备。适宜的碱包括碳酸钾和碳酸钠,氢氧化钾和氢氧化钠,以及氢化钠。该反应适宜在溶剂如二甲基甲酰胺、二噁烷、THF、环丁砜和乙腈中进行。该反应是本领域技术人员已知的。
图示4:
式(VI)化合物可以例如通过将式(IV)化合物(其中E1和E2均为卤素)与甲硫醇的钠盐或钾盐的四氢呋喃或二噁烷溶液反应加以制备。该反应是本领域技术人员已知的。
其中E1和E2均为卤素的式(IV)化合物也是商购可得的或可根据本领域技术人员已知的方法加以制备的。这类本领域技术人员已知的方法描述于例如Advances in Heterocyclic Chemistry,Katritzky,A.R.,Ed.,Academic Press,New York,1993,第58卷,第301至305页;Heterocyclic Compounds,Elderfield,R.C.,Ed.,JohnWiley,New York,1957,第6卷,第265至270页中。
式(V)的吡唑化合物可通过本领域技术人员已知的方法加以制备的。例如4-三氟甲基吡唑的制备描述于THL,37,11,1996,第1829-1832页。
本发明的式(I)化合物具有控制广谱性经济重要的单子叶和双子叶杂草优良的除草活性。该活性物质也同样有效地控制从根茎、根状茎或其它多年生器官发芽的,并且难于控制的多年生杂草。在本文中,该活性物质是否是播种前、苗前或苗后施用是无关紧要的。在具体的实施例中例举可由本发明的化合物控制的一些单子叶和双子叶杂草植物的代表,其并不用于限制特定种类。在单子叶杂草种类中,能有效控制的例如一年生杂草的主要有燕麦草、黑麦草、看麦娘、虉草、稗草、马唐、狗尾草和莎草,以及多年生的小麦草、狗牙根、白茅和高梁,以及多年生的莎草。在双子叶杂草中,作用谱扩大至如下种类,例如一年生的猪殃殃、堇菜、婆婆纳、野芝麻、繁缕、苋、白芥、牵牛花、母菊、苘麻、黄花稔,及多年生的旋花、蓟、酸模、蒿。本发明的活性成份也能显著地控制发生于特定的水稻生长条件下的有害植物如例如稗草、慈姑、泽泻、荸荠、藨草及莎草。如果在苗前将本发明的化合物施加于土壤表面,则完全阻止杂草出苗,或杂草植物生长至子叶期就停止生长,最后在经过三至四周之后就完全死亡。当将活性物质苗后施用至植物绿色部分,在处理后的极短时间内生长急剧停止,并且杂草停留在施药时的生长期,或在一定时间之后完全死亡,从而以这种方式在早期并且持续地消除对作物有害的杂草竞争。特别地,本发明化合物具有控制下列杂草的显著作用:反枝苋、燕麦属、稗属、水莎草、多花黑麦草、狗尾草、矮慈姑、萤蔺、白芥属和繁缕。
尽管本发明的化合物控制单子叶和双子叶杂草具有显著的除草活性,但对具有经济重要意义的作物例如小麦、大麦、黑麦、水稻、玉米、甜菜、棉花和大豆则仅有可忽略程度的损害。特别地,本发明化合物在小麦、玉米、水稻和大豆中显示良好的耐受性。这就是本发明化合物高度适用于在有用的农作物或观赏植物上选择性地控制不需要的植物生长的原因。
由于其除草性质,该活性物质也可用于控制已知作物或仍在开发中的转基因植物中的杂草。通常来说,转基因植物通常具有特别优越的性质,例如对某些农药的抗性,尤其是某些除草剂,对植物病害或植物病害病原体的抗性,例如某些昆虫或微生物如真菌、细菌或病毒。其它的特殊性质涉及例如收成产物的数量、质量、储藏性能、组分和特定成分。因此,转基因植物以经提高的淀粉含量或经改良的淀粉品质,或那些具有不同的脂肪酸组分的收成产物而著称。
本发明的式(I)化合物或其盐优选用于具经济重要性的有用植物和观赏植物的转基因作物,例如谷类如小麦、大麦、黑麦、燕麦、粟、水稻、木薯和玉米,或其它作物如甜菜、棉花、大豆、油菜、土豆、西红柿、豌豆和其它植物。式(I)化合物可优选地作为除草剂用于针对除草剂毒性作用耐受的或通过基因工程技术使之耐受的有用作物中。
传统的培育比已知植物具有改良性质的新颖植物的方式包括例如经典的培育方法和突变种的制造。可选择的是,借助基因工程方法可产生具有改良性质的新颖植物(参照例如EP-A-0221044、EP-A-0131624)。例如,下列的几项描述:
-用基因技术改变植作物用于改良植物中合成的淀粉(例如WO92/11376、WO 92/14827及WO 91/19806),
-对抗草铵膦型(参见例如EP-A-0242236、EP-A-242246)、草甘膦型(WO 92/00377)或磺酰脲型(EP-A-0257993、US-A-5013659)的特定除草剂的转基因作物植物。
-具有产生苏云金芽孢杆菌毒素(Bt毒素)能力的转基因作物,例如棉花,使该植物对抗特定害虫(EP-A-0142924,EP-A-0193259)。
-具有改良脂肪酸组成的转基因作物(WO 91/13972)。
大量可制备具有改良性质的新颖转基因植物的分子生物技术基本上是已知的;参照例如,Sambrook等,1989,Molecular Cloning,ALaboratory Manual,2nd ed.Cold Spring Harbor Laboratory Press,Cold Spring Harbor,NY;或Winnacker“Gene und Klone”,VCHWeinheim,2nd edition 1996,或Christou,“Trends in PlantScience”1(1996)423-431。
为了进行此类的遗传改造,可以将核酸分子导入质粒中,其可通过DNA序列的重组使序列发生诱变或改变。使用上述提到的标准方法,可以例如调换碱基、部份序列去除或加入天然序列或合成序列。为了使DNA片段彼此连结可以将接合体或连接体与片段连结。
具有降低活性的基因产物的植物细胞可以例如通过下列方式制备:表达至少一种相应的反义RNA、有义RNA达到协同抑制效果,或表现至少一种相应的经构筑的核糖酶,其特异性切割上述提到的基因产物的转录本。
对此即可以使用一种DNA分子,其含有基因产物的全部的编码序列(包括可能存在的两侧翼序列),也可以使用一种DNA分子,其只含有部分的编码序列,该序列部份必须足够长以引起细胞的反义效果。也可以使用DNA序列,其具有与基因产物的编码序列高度的同源性,但不是完全地相同。
在植物中表达核酸分子时,经合成的蛋白质可定位于植物细胞的任意区室内。然而,要达到定位于某一特定区室,可以例如使编码区与确保特定区室定位的DNA序列连结。此类序列是本领域技术人员所熟悉的(参见例如,Braun等,EMBO J.11(1992),3219-3227;Wolter等,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等,Plant J.1(1991),95-106)。
使用已知的技术可以使转基因植物细胞再生成整株植物。该转基因植物基本上可以是任意一种植物种类的植物,既包括单子叶植物又包括双子叶植物。
由于同源的(既天然的)基因或基因序列的过度表达,遏抑或抑制,或通过异源的(即外来的)基因或基因序列的表达可以获得具有经改变的性质的转基因植物。
当将本发明活性物质用于转基因作物时,除了在其它作物上通常可观察到的抗杂草植物的效果之外,对于所述转基因作物具有特定的效果,例如改良的或特别扩展可控制的杂草谱,可用于施用的改良的施用量,优选与转基因作物有抗性的除草剂的良好结合性,以及对转基因作物的生长和产量的影响。因此,本发明还提供了将本发明化合物作为除草剂用于控制转基因作物中杂草的用途。
此外,本发明的物质对作物具有突出的生长调节性。它们调节性地参与植物的新陈代谢,因此可通过例如引发脱水和生长充实而有目的地影响植物成分并且促进收获。此外,也适用于一般性控制并且抑制不期望的植物生长,而同时不伤害植物。由于可减少或完全预防引起产量降低的作物倒伏,植物生长的抑制在许多单子叶及双子叶作物中扮演着重要的角色。
本发明的化合物可以下列常规制剂形式施用:可湿性粉剂、乳油、可喷洒溶液、粉剂或颗粒剂。因此,本发明进一步涉及包含式(I)化合物的除草组合物。分别视其主要的生物和/或物理化学参数而定,可以各种方式配制式(I)化合物。适宜的制剂实例为:水溶性粉剂(SP)、可湿性粉剂(WP)、水溶性浓缩物、乳油(EC)、乳液(EW)如水包油及油包水乳液、可喷洒溶液、悬浮浓缩物(SC)、油或水基的分散剂、油溶溶液、胶囊悬浮剂(CS)、粉剂(DP)、浸种组合物、土壤施用或播散粒剂、以微粒、喷洒颗粒、涂覆颗粒和吸附性颗粒形式的粒剂(GR),水分散性颗粒剂(WG)、水溶性颗粒(SG)、ULV制剂、微型胶囊类和蜡类。所述各种制剂类型基本上是已知的,并例如在:Winnacker-Küchler,“Chemische Technologie(化学技术)”,第7册,C.Hauser Verlag München,第四版,1986;Wade van Falkenberg,“Pesticides Formulations(农药制剂)”,Marcel Dekker N.Y.,1973;K.Martens,“喷雾干燥手册(Spray Drying Handbook)”,第三版,1979,G.Goodwin Ltd.London中有描述。
所述必要的助剂,如惰性材料、表面活性剂、溶剂及其它的添加剂同样是已知的并例如在:Watkins,“Handbook of Insecticide DustDiluents and Carrier(杀虫粉尘稀释液和载体手册)”,第二版,Darland Books,Caldwell N.J.;H.v.Olphen,“Introduction to ClayColloid Chemistry(粘土胶体化学入门)”,第二版,J.Wiley & Sons,N.Y.;C.Marsden,“Solvents Guide(溶剂指南)”,第二版,Interscience,N.Y.1963;McCutcheon′s,“Detergents andEmulsifiers Annual”,MC Publ.Corp.,Ridgewood N.J.;Sisley andWood,“Encyclopedia of surface Active Agents(表面活性剂百科全书)”,Chem.Publ.Co.Inc.,N.Y.1964;Schnfeldt,“Grenzflchenaktive thylenoxid-addukte(表面活性的环氧乙烷加成物)”,Wiss Verlagsgesell.,Stuttgart 1976;Winnacker-Küchler,“Chemische Technologie”,第7册,C.HauserVerlag München,第四版,1986中有描述。
可湿性粉剂是均匀分散在水中的制剂,其除了活性物质和稀释剂或惰性物质外,还含有离子型或非离子型表面活性剂(润湿剂、分散剂),例如:聚乙氧基化的烷基酚类、聚乙氧基化的脂肪醇类或脂肪胺类、脂肪醇聚二醇醚硫酸酯、烷磺酸酯类或烷基苯磺酸酯类、木质磺酸钠、2,2′-二萘甲烷-6,6′-二磺酸钠、二丁基萘磺酸钠或油酰甲基牛磺酸钠。制备可湿性粉剂时,将除草活性物质磨细,例如在常用装置中如锤磨机、鼓风磨机和喷气磨机中磨细,同时或随后与助剂混合。
乳油的制备是通过将活性物质溶解在有机溶剂中,如丁醇、环己酮、二甲基甲酰胺、二甲苯或其它沸点较高的芳族或烃或添加一个或多个离子型和/或非离子型表面活性剂(乳化剂)的有机溶剂混合物。可以使用的乳化剂的实例是:烷芳基磺酸的钙盐(如十二烷基苯磺酸钙)或非离子型乳化剂,如脂肪酸聚乙二醇酯、烷芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷/环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯例如脱水山梨糖醇脂肪酸酯或聚氧乙烯山梨糖醇酯,例如聚氧乙烯脱水山梨糖醇脂肪酸酯。
粉剂是将活性物质与磨成细粉状的固体物质加以磨碎而得,所述固体物质例如:滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮剂可为水基或油基。例如,该制剂在视需要添加上述其它制剂类型实例中的表面活性剂下,可通过利用常规的球磨机湿磨制得。
乳液例如水包油乳液(EW)的制备可以利用含水的有机溶剂,借助搅拌器、胶体研磨器和/或静态混合器,并且视需要可加入例如上述其它制剂类型实例中的表面活性剂。
粒剂的制备可以通过将活性物质喷洒在吸附性粒状的惰性物质上,或将活性物质浓缩物借助粘合剂(如聚乙烯醇,聚丙烯酸钠或矿物油)涂敷在载体(如砂、高岭土或粒状惰性物质)的表面上。适宜的活性物质可以使用制造肥粒颗料的常规方法并视需要与肥料的混合物一同粒化。
水分散性粒剂通常是利用常规方法如喷雾式干燥法、流体化床式制粒法、碟式制粒法、用高速搅拌器混合法混合和无固体惰性物质的挤压制备而成。
关于碟式、流化床、挤压机和喷撒颗粒剂的制备方法,参见下述工艺,例如“Spray-Drying Handbook”(喷雾干燥手册)第3版,1979年,G.Goodwin Ltd.,London;J.E.Browning,“Agglomeration”(团聚作用),Chemical and Engineering(化学和工程)1967,pages147 et seq.;“Perry′s Chemical Engineer′s Handbook”(Perry′s化学工程师手册),第5版,McGraw-Hill,New York 1973,第8-57页。
对于更详细的作物保护剂制剂参见,例如G.C.Klingman,“WeedControl as a Science”(杂草控制科学),John Wiley and Sons,Inc.,New York,1961,第81-96页和J.D.Freyer,S.A.Evans,“Weed Control Handbook”(杂草控制手册),第5版,BlackwellScientific Publications,Oxford,1968,第101-103页。
该农业化学制剂通常含有0.1~99重量%,尤其是0.1~95重量%的式(I)活性物质。可湿性粉剂中,活性物质的浓度通常为约10~90重量%,至100重量%的余量由常规制剂组分构成。在乳油中,活性物质的浓度可为约1~90重量%,优选5~80重量%。粉剂形式的制剂通常含有1~30重量%的活性物质,大多情况下优选5~20重量%的活性物质,而可喷雾型溶液含有约0.05~80重量%,优选2~50重量%的活性物质。水分散颗粒剂中,活性物质的含量部分取决于活性化合物是否以液态或固态形式,以及取决于使用的粒化助剂和填料等。水分散颗粒剂中,活性物质的含量为例如介于1和95重量%,优选介于10和80重量%之间。
此外,上述活性物质制剂可视需要分别包含常用的粘合剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、防冻剂、溶剂、填料、载体、着色剂、消泡剂、蒸发抑制剂、pH调节剂和粘度调节剂。
以该配制品为基础,也可以制备具有其它农药活性物质的组合物,例如杀虫剂、杀螨剂、除草剂、杀菌剂,以及安全剂、肥料和/或植物生长调节剂,例如以预混物或桶混物形式。
以混合制剂或桶混物形式可与本发明活性物质组合的活性物质例如可使用已知的活性物质,例如在Weed Research 26,441-445,(1986),或“The Pesticide Manual”(农药手册),第11版,TheBritish Crop Protection Council and the Royal Soc.,of Chemistry,1997及其中所列的文献所描述的。例如,可提及的并且可与式(I)化合物相组合的已知除草剂为例如下述活性物质(注:所述化合物根据国际标准化组织(ISO)以通用名表示或采用化学名称,视需要与其常用编码一起表示):
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、苯草醚(aclonifen)、AKH 7088,即[[[1-[5-[2-氯基-4-(三氟甲基)苯氧基]-2-硝苯基]-2-甲氧基亚乙基]氨基]氧基]乙酸及其甲酯、甲草胺(alachlor)、禾草灭(alloxydim)、莠灭净(ametryn)、酰嘧磺隆(amidosulfuron)、杀草强(amitrol)、AMS(即氨基磺酸酯)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、四唑嘧磺隆(azimsulfurone)(DPX-A8947)、叠氮津(aziprotryn)、燕麦灵(barban)、BAS 516H(即5-氟-2-苯基-4H-3,1-苯并噁嗪-4-酮)、草除灵(benazolin)、氟草胺(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、吡草酮(benzofenap)、氟磺胺草(benzofluor)、乙基新燕灵(benzoylprop-ethyl)、噻草隆(benzthiazuron)、双丙氨酰膦(bialaphos)、治草醚(bifenox)、除草定(bromacil)、溴丁酰草胺(bromobutide)、杀草全(bromofenoxim)、溴苯腈(bromoxynil)、bromuron、特克草(buminafos)、羟草酮(busoxinone)、丁草胺(butachlor)、抑草膦(butamifos)、丁烯草胺(butenachlor)、草噻咪(buthidazole)、地乐胺(butralin)、苏达灭(butylate)、唑酰草胺(Cafenstrole)(CH-900)、双酰草胺(Carbetamide)、唑酮草酯(Carfentrazone)(ICI-A0051)、CDAA(即2-氯-N,N-二-2-丙烯基乙酰胺)、CDEC(即二乙基二硫代氨基甲酸2-氯烯丙酯)、氯硝醚(Chlomethoxyfen)、草灭平(Chloramben)、炔禾灵(Chlorazifop-butyl)、Chlormesulon(ICI-A0051)、氯溴隆(Chlorbromuron)、氯草灵(Chlorbufam)、伐草克(Chlorfenac)、氯甲丹(Chlorflurecol-methyl)、杀草敏(Chloridazon)、氯嘧黄隆(Chlorimuron-ethyl)、草枯醚(Chlornitrofen)、绿麦隆(Chlorotoluron)、枯草隆(Chloroxuron)、氯苯胺灵(Chlorpropham)、chloraulfuron;敌草索(Chlorthal-dimethyl)、草克乐(Chlorthiamid)、环庚草醚(Cinmethylin)、醚黄隆(Cinosulfuron)、烯草酮(Clethodim)、炔草酯(Clodinafop)及其酯衍生物(例如炔草酯-炔丙基)、稗草胺(Clomeprop)、环己烯草酮(Cloproxydim)、二氯吡啶酸(clopyralid)、Cumyluron(JC 940)、草净津(Cyanazine)、草灭特(Cycloate)、环丙黄隆(Cyclosulfamuron)(AC 104)、噻草酮(Cycloxydim)、环莠隆(Cycluron)、氰氟草酯(Cyhalofop)及其酯衍生物(例如丁酯,DEH-112)、莎草快(Cyperquat)、环草津(Cyprazine)、环唑草胺(Cyprazole)、香草隆(daimuron)、2,4-DB、茅草枯(dalapon)、甜菜安(desmedipham)、敌草净(desmetryn)、燕麦敌(di-Allate)、麦草畏(dicamba)、敌草腈(dichlobenil)、2,4-滴丙酸(dichlorprop)、禾草灵(diclofop)及其酯类(如甲基禾草灵)、乙酰甲草胺(diethatyl);枯莠隆(difenoxuron)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、噁唑隆(dimefuron)、二甲草胺(dimethachlor);异戊乙净(dimethametryn)、噻吩草胺(dimethenamid)(SAN-582H)、异恶草松(dimethazone)、异恶草松(clomazon)、噻节因(dimethipin)、dimetrasulfuron、敌乐胺(dinitramine)、地乐酚(dinoseb)、特乐酚(dinoterb)、双甲酰草胺(diphenamid)、异丙净(dipropetryn)、草乃敌(diquat)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、草止津(eglinazine-ethyl)、EL 77(即5-氰基-1-(1,1-二甲乙基)-N-甲基-1H-吡唑-4-碳酰胺)、草藻灭(endothal)、EPTC、禾草畏(esprocarb)、丁氟消草(ethalfluralin)、胺苯黄隆(ethametsulfuron-methyl)、噻二唑隆(ethidimuron)、嗪丁草(ethiozin)、乙呋草黄(ethofumesate)、F5231(即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙烷磺酰胺、氯氟草醚(ethoxyfen)及其酯类(例如乙酯,HN-252)、乙氧苯草胺(etobenzanid)(HW 52)、2,4,5-涕丙酸(fenoprop)、Fenoxan、噁唑禾草灵(fenoxaprop)及高噁唑禾草灵及其酯(例如高噁唑禾草灵乙酯和噁唑禾草灵乙酯)、Fenoxydim、非草隆(fenuron)、氟燕灵(flamprop-methyl)、啶嘧黄隆(flazasulfuron)、吡氟禾草灵(fluazifop)和精吡氟禾草灵及其酯类(例如吡氟禾草灵丁酯和精吡氟禾草灵丁酯)、氟消草(fluchloralin)、氟唑啶草(flumetsulam)、Flumeturon、酰亚胺苯氧乙酸(flumiclorac)及其酯(例如戊酯,S-23031)、氟噁嗪酮(flumioxazin)(S-482)、Flumipropyn、氟胺草唑(flupoxam)(KNW-739)、三氟硝草醚(fluorodifen)、乙羧氟草醚(fluoroglycofen-ethyl)、Flupropacil(UBIC-4243)、氟草酮(fluridone)、氟咯草酮(flurochloridone)、氟草烟(fluroxypyr)、呋草酮(flurtamone)、氟黄胺草醚(fomesafen)、膦铵素(fosamine)、氟呋草醚(furyloxyfen)、草铵膦(glufosinate)、草甘膦(glyphosate)、氟硝磺酰胺(halosafen)、吡氯黄隆(halosulfuron)及其酯(例如甲酯,NC-319)、吡氟氯禾灵(haloxyfop)及其酯、精吡氟氯禾灵(即R-haloxyfop)及其酯、六嗪酮(hexazinone)、灭草烟(imazapyr)、咪草酸(imazamethabenz-methyl)、灭草喹(imazaquin)及盐类如铵盐、碘苯腈(ioxynil)、Imazamethapyr、咪唑乙烟酸(imazethapyr)、咪唑磺隆(imazosulfuron)、丁环隆(isocarbamid)、异乐灵(isopropalin)、异丙隆(isoproturon)、异噁隆(isouron)、异噁草胺(isoxaben)、草醚(isoxapyrifop)、卡草灵(karbutilate)、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、2甲4氯(MCPA)、2甲4氯丁酸(MCPB)、2甲4氯丙酸(mecoprop)、苯噻草胺(mefenacet)、氟草磺(mefluidid)、苯嗪草酮(metamitron)、吡草胺(metazachlor)、噻唑隆(metham)、甲基苯噻隆(methabenzthiazuron)、灭草唑(methazole)、去草酮(methoxyphenone)、苯丙隆(methyldymron)、色满隆(metabenzuron)、methobenzuron、秀谷隆(metobromuron)、异丙甲草胺(metolachlor)、唑草磺胺(metosulam)(XRD 511)、甲氧隆(metoxuron)、赛克津(metribuzin)、甲黄隆(metsulfuron-methyl)、MH、草达灭(molinate);杀草利(monalide)、绿谷隆(monolinuron)、灭草隆(monuron)、单脲硫酸二氢酯(monocarbamide dihydrogensulfate)、MT 128(即6-氯-N-(3-氯-2-丙烯基)-5-甲基-N-苯基-3-哒嗪胺)、MT 5950(即N-[3-氯基-4-(1-甲基乙基)-苯基]-2-甲基戊酰胺)、萘草胺(naproanilide)、草萘胺(napropamide)、抑草止(naptalam)、NC 310(即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑)、草不隆(neburon)、烟嘧黄隆(nicosulfuron)、nipyraclophen、磺乐灵(Nitralin)、除草醚(nitrofen)、硝氟草醚(nitrofluorfen)、达草灭(Norfluazon)、坪草丹(Orbencarb)、黄草消(oryzalin)、炔丙噁唑草(Oxadiargyl)(RP-020630)、噁草灵(Oxadiazon)、环丙氧黄隆(0xasulfuron)、对草快(Paraquat)、克草猛(Pebulate)、胺硝草(pendimethalin)、氟草磺胺(perfluidone)、敌草克(phenisopham)、苯敌草(Phenmedipham)、毒莠定(Picloram)、派草磷(piperophos)、Piributicarb、Pirifenop-butyl、丙草胺(pretilachlor)、氟嘧黄隆(primisulfuron-methyl)、环氰津(procyazine)、氨基丙氟灵(prodiamine)、环丙氟灵(profluralin)、丙草止津(proglinazine-ethyl)、扑灭通(prometon)、扑草净(prometryn)、毒草安(propachlor)、敌稗(propanil)、喔草酯(propaquizafop)及其酯、扑灭津(Propazine)、苯胺灵(Propham)、异丙草胺(propisochlor)、拿草特(propyzamide)、磺亚胺草(prosulfalin)、苄草丹(prosulfocarb)、氟丙黄隆(prosulfuron)(CGA-152005)、广草胺(prynachlor)、吡唑特(pyrazolinate)、杀草敏(Pyrazon)、吡嘧黄隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、达草止(pyridate)、嘧硫苯甲酸(pyrithiobac)(KIH-2031)、Pyroxofop及其酯(例如炔丙酯)、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、Quinofop及其酯衍生物、喹禾灵(quizalofop)和精喹禾灵及其酯衍生物例如喹禾灵乙酯、精喹禾灵四氢糠基酯和精喹禾灵乙酯、renriduron、玉嘧黄隆(rimsulfuron)(DPX-E9636)、S 275(即2-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-4,5,6,7-四氢-2H-吲唑)、密草通(secbumeton)、稀禾定(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SN 106279(即2-[[7-[2-氯-4-(三氟甲基)苯氧基]-2-萘基]氧基]丙酸及其甲酯)、磺胺草唑(sulfentrazon)(FMC-97285,F-6285)、Sulfazuron、嘧黄隆(sulfometuron-methyl)、甲嘧磺隆(sulfosate)(ICI-A0224)、TCA、丙戊草胺(tebutam)(GCP-5544)、丁唑隆(tebuthiuron)、特草定(terbacil)、芽根灵(terbucarb)、猛杀草(terbuchlor)、甲氧去草净(terbumeton)、特丁津(terbtylazine)、去草净(terbutryn)、TFH 450(即N,N-二乙基-3-[(2-乙基-6-甲基苯基)磺酰基]-1H-1,2,4-三唑-1-碳酰胺)、噻醚草胺(thenylchlor)(NSK-850)、赛唑隆(thiazafluron)、噻氟啶草(thiazopyr)(Mon-13200)、噻二唑胺(thidiazimin)(SN-24085)、杀草丹(thiobencarb)、噻黄隆(thifensulfuron-methyl)、丁草威(tiocarbazil)、肟草酮(tralkoxydim)、野麦畏(tri-allate)、醚苯黄隆(triasulfuron)、Triazofenamide、苯黄隆(tribenuron-methyl)、定草酯(triclopyr)、灭草环(tridiphane)、草达津(trietazine)、氟乐灵trifluralin)、氟胺黄隆及酯(例如甲酯,DPX-66037)、三甲隆(trimeturon)、tsitodef、灭草猛(vernolate)、WL 110547(即5-苯氧基-1-[3-(三氟甲基)-苯基]-1H-四唑、UBH-509、D-489、LS82-556、KPP-300、NC-324、NC-330、KH-218、DPX-N8189、SC-0774、DOWCO-535、DK-8910、V-53482、PP-600、MBH-001、KIH-9201、ET-751、KIH-6127及KIH-2023。
对于使用,将商购可得形式的制剂以常规方式稀释,例如在可湿性粉剂、乳油、分散剂和水分散颗粒剂中用水稀释。粉剂、土壤颗粒剂、撒布的颗粒剂和可喷雾溶液形式的制剂通常在使用前不用任何其它多项物质稀释。所需式(I)化合物的施用量随着外部环境而变化,例如尤其是温度、湿度和所采用除草剂的性质。该施用量可以在宽范围类变化,例如介于0.001和1.0kg/ha之间或更多的活性物质,但是优选介于0.005和750g/ha之间。
下面的实施例进一步说明本发明。
A.化学实施例
制备5-甲基-4-(3-三氟甲基苯氧基)-2-(4-三氟甲基-1H-1-吡唑基)嘧啶:
在200ml的DMF中,将11.2g(36.4mmol)的5-甲基-4-甲基磺酰基-2-(4-三氟甲基-1H-1-吡唑基)嘧啶、7.7g(47.4mmol)的3-三氟甲基苯酚和10.1g(72.9mmol)的K2CO3的混合物于室温下搅拌24小时。随后注入200ml水并各用100ml的CH2Cl2萃取四次。将合并的有机相在Na2SO4上干燥,过滤并浓缩。在硅胶上采用庚烷/乙酸乙酯(1∶1)作为洗脱液进行色谱纯化,获得10.2g(72%)熔点为103-105℃,无色结晶状的5-甲基-4-(3-三氟甲基苯氧基)-2-(4-三氟甲基-1H-1-吡唑基)嘧啶。
1H-NMR:δ[CDCl3]2.40(s,3H),7.45(m,1H),7.55(s,1H),7.62(m,2H),7.92(s,1H),8.33(s,1H),8.52(s,1H)。
制备5-甲基-2-(4-三氟甲基)-1H-1-吡唑基-4-(2-三氟甲基-4-吡啶基氧基)嘧啶:
在10ml的DMF中,将0.38g(1.23mmol)的5-甲基-4-甲基磺酰基-2-(4-三氟甲基-1H-1-吡唑基)嘧啶、0.2g(1.23mmol)的2-三氟甲基-4-羟基吡啶和0.33g(2.45mmol)的K2CO3的混合物于60℃下搅拌6小时,并随后于室温下搅拌48小时。然后向该混合物中注入20ml水并且各用15ml的CH2Cl2萃取四次。将合并的有机相在Na2SO4上干燥,过滤并浓缩。在硅胶上采用庚烷/乙酸乙酯(3∶7)作为洗脱液进行色谱纯化,获得0.16g(33%)淡黄色油状的5-甲基-2-(4-三氟甲基)-1H-1-吡唑基-4-(2-三氟甲基-4-吡啶基氧基)嘧啶。
1H-NMR:δ[CDCl3]2.40(s,3H),7.50(dd,1H),7.70(d,1H),7.95(s,1H),8.50(s,1H),8.60(s,1H),8.85(d,1H)。
制备2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶:
将0.262g的4-三氟甲基吡唑在氮气下预置于7ml的二甲基乙酰胺中,并且在0℃下加入0.057g的NaH。使该混合物于30分钟内达到室温,并且随后加入0.5g的2-氟-6-(1-甲基-3-三氟甲基吡唑-5-基氧基)吡啶,并将该混合物在140℃加热7小时,随后冷却至室温并且注入水。将产物用庚烷/乙酸乙酯(1∶1)萃取两次后,用水和饱和氯化钠溶液洗涤,在MgSO4上干燥并进行浓缩。在硅胶上进行色谱纯化获得0.349g白色结晶状的2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶。
1H-NMR:δ[CDCl3]3.82(s,3H),6.34(s,1H),7.00(d,1H),7.82(d,1H),7.88(s,1H),7.97(t,1H),8.43(s,1H)。
制备4-甲基-2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶:
将0.385g的4-三氟甲基吡唑在氮气下预置于10ml的二甲基乙酰胺中,并且在0℃下加入0.096g的NaH。使该混合物于30分钟内达到室温,并且随后加入0.757g的2-氯-4-甲基-6-(1-甲基-3-三氟甲基吡唑-5-基氧基)吡啶并将该混合物在140℃加热7小时,随后冷却至室温并且注入水。将产物用乙酸乙酯/庚烷(1∶1)萃取两次并用乙酸乙酯萃取两次,随后用水和饱和氯化钠溶液洗涤,在MgSO4上干燥并进行浓缩。在硅胶上进行色谱纯化获得0.332g白色结晶状的4-甲基-2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶。
1H-NMR:δ[CDCl3]2.50(s,3H),3.82(s,3H),6.30(s,1H),6.82(d,1H),7.67(s,1H),7.86(s,1H),8.43(s,1H)。
制备4-甲氧基-2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶:
将0.068g的4-三氟甲基吡唑在氮气下预置于5ml的二甲基乙酰胺中,并且在0℃下加入0.017g的NaH。使该混合物于30分钟内达到室温,并且随后加入0.2g的4-甲氧基-2,6-二(1-甲基-3-三氟甲基吡唑-5-基氧基)吡啶,并将该混合物在135℃加热5小时,冷却至室温并且注入水。将产物用乙酸乙酯/庚烷(1∶1)萃取三次,用水和饱和氯化钠溶液洗涤,在MgSO4上干燥并进行浓缩。在硅胶上进行色谱纯化获得0.036g蜡状的4-甲氧基-2-(1-甲基-3-三氟甲基吡唑-5-基氧基)-6-(4-三氟甲基吡唑-1-基)吡啶。
1H-NMR:δ[CDCl3]3.81(s,3H),3.99(s,3H),6.29(s,1H),6.44(d,1H),7.40(d,1H),7.85(s,1H),8.42(s,1H)。
列于下表中的实施例以类似于上述方法进行制备或是以类似于上述方法可获得的。
这里使用的缩写具有如下定义:
Et=乙基 OEt=乙氧基 Me=甲基
OMe=甲氧基 EE=乙酸乙酯 m.p.=熔点
Rf=保留值 i-Pr=异丙基 n-Pr=正丙基
RT=室温
表1:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y1 R6=H
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.1 | H | H | H | H | CF3 | N | 1H-NMR(CDCl3):6.90(d,1H);7.45(m,1H);7.55(m,1H);7.62(m,2H);7.98(s,1H);8.50(s,1H);8.70(d,1H) |
1.2 | H | H | H | H | CF3 | CH | m.p.55-56℃ |
1.3 | H | H | H | H | CF3 | CMe | |
1.4 | H | H | H | H | CF3 | CCl | |
1.5 | H | H | Me | H | CF3 | CH | |
1.6 | H | OH | H | Me | CF3 | CH | |
1.7 | H | Me | H | H | CF3 | N | m.p.103-105℃ |
1.8 | H | OMe | H | H | CF3 | CH | |
1.9 | H | H | H | H | Cl | N | |
1.10 | H | H | H | H | Cl | CH | |
1.11 | H | H | H | H | Cl | CMe | |
1.12 | H | H | H | H | Cl | CCl | |
1.13 | H | H | Me | H | Cl | CH | |
1.14 | H | OH | H | Me | Cl | CH | |
1.15 | H | Me | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.16 | H | OMe | H | H | Cl | CH | |
1.17 | H | H | H | H | CN | N | |
1.18 | H | H | H | H | CN | CH | m.p.86-88℃ |
1.19 | H | H | H | H | CN | CMe | |
1.20 | H | H | H | H | CN | CCl | |
1.21 | H | H | Me | H | CN | CH | |
1.22 | H | OH | H | Me | CN | CH | |
1.23 | H | Me | H | H | CN | CH | |
1.24 | H | OMe | H | H | CN | CH | |
1.25 | H | H | H | H | OCF2H | N | |
1.26 | H | H | H | H | OCF2H | CH | |
1.27 | H | H | H | H | OCF2H | CMe | |
1.28 | H | H | H | H | OCF2H | CCl | |
1.29 | H | H | Me | H | OCF2H | CH | |
1.30 | H | OH | H | Me | OCF2H | CH | |
1.31 | H | Me | H | H | OCF2H | CH | |
1.32 | H | OMe | H | H | OCF2H | CH | |
1.33 | H | H | H | H | CN | N | |
1.34 | H | H | H | H | CN | CH | |
1.35 | H | H | H | H | CN | CMe | |
1.36 | H | H | H | H | CN | CCl | |
1.37 | H | H | Me | H | CN | CH | |
1.38 | H | OH | H | Me | CN | CH | |
1.39 | H | Me | H | H | CN | CH | |
1.40 | H | OMe | H | H | CN | CH | |
1.41 | H | H | H | H | CN | N | |
1.42 | H | H | H | H | CN | CH | |
1.43 | H | H | H | H | CN | CMe | |
1.44 | H | H | H | H | CN | CCl | |
1.45 | H | H | Me | H | CN | CH | |
1.46 | H | OH | H | Me | CN | CH | |
1.47 | H | Me | H | H | CN | CH | |
1.48 | H | OMe | H | H | CN | CH | |
1.49 | Me | H | H | H | CF3 | N | m.p.109-111℃ |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.50 | Me | H | H | H | CF3 | CH | |
1.51 | Me | H | H | H | CF3 | CMe | |
1.52 | Me | H | H | H | CF3 | CCl | |
1.53 | Me | H | Me | H | CF3 | CH | |
1.54 | Me | OH | H | Me | CF3 | CH | |
1.55 | Me | Me | H | H | CF3 | CH | |
1.56 | Me | OMe | H | H | CF3 | CH | |
1.57 | Me | H | H | H | Cl | N | |
1.58 | Me | H | H | H | Cl | CH | |
1.59 | Me | H | H | H | Cl | CMe | |
1.60 | Me | H | H | H | Cl | CCl | |
1.61 | Me | H | Me | H | Cl | CH | |
1.62 | Me | OH | H | Me | Cl | CH | |
1.63 | Me | Me | H | H | Cl | CH | |
1.64 | Me | OMe | H | H | Cl | CH | |
1.65 | Me | H | H | H | CN | N | |
1.66 | Me | H | H | H | CN | CH | |
1.67 | Me | H | H | H | CN | CMe | |
1.68 | Me | H | H | H | CN | CCl | |
1.69 | Me | H | Me | H | CN | CH | |
1.70 | Me | OH | H | Me | CN | CH | |
1.71 | Me | Me | H | H | CN | CH | |
1.72 | Me | OMe | H | H | CN | CH | |
1.73 | Me | H | H | H | OCF2H | N | |
1.74 | Me | H | H | H | OCF2H | CH | |
1.75 | Me | H | H | H | OCF2H | CMe | |
1.76 | Me | H | H | H | OCF2H | CCl | |
1.77 | Me | H | Me | H | OCF2H | CH | |
1.78 | Me | OH | H | Me | OCF2H | CH | |
1.79 | Me | Me | H | H | OCF2H | CH | |
1.80 | Me | OMe | H | H | OCF2H | CH | |
1.81 | Me | H | H | H | CN | N | |
1.82 | Me | H | H | H | CN | CH | |
1.83 | Me | H | H | H | CN | CMe |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.84 | Me | H | H | H | CN | CCl | |
1.85 | Me | H | Me | H | CN | CH | |
1.86 | Me | OH | H | Me | CN | CH | |
1.87 | Me | Me | H | H | CN | CH | |
1.88 | Me | OMe | H | H | CN | CH | |
1.89 | Me | H | H | H | CN | N | |
1.90 | Me | H | H | H | CN | CH | |
1.91 | Me | H | H | H | CN | CMe | |
1.92 | Me | H | H | H | CN | CCl | |
1.93 | Me | H | Me | H | CN | CH | |
1.94 | Me | OH | H | Me | CN | CH | |
1.95 | Me | Me | H | H | CN | CH | |
1.96 | Me | OMe | H | H | CN | CH | |
1.97 | CN | H | H | H | CF3 | N | |
1.98 | CN | H | H | H | CF3 | CH | |
1.99 | CN | H | H | H | CF3 | CMe | |
1.100 | CN | H | H | H | CF3 | CCl | |
1.101 | CN | H | Me | H | CF3 | CH | |
1.102 | CN | OH | H | Me | CF3 | CH | |
1.103 | CN | Me | H | H | CF3 | CH | |
1.104 | CN | OMe | H | H | CF3 | CH | |
1.105 | CN | H | H | H | Cl | N | |
1.106 | CN | H | H | H | Cl | CH | |
1.107 | CN | H | H | H | Cl | CMe | |
1.108 | CN | H | H | H | Cl | CCl | |
1.109 | CN | H | Me | H | Cl | CH | |
1.110 | CN | OH | H | Me | Cl | CH | |
1.111 | CN | Me | H | H | Cl | CH | |
1.112 | CN | OMe | H | H | Cl | CH | |
1.113 | CN | H | H | H | CN | N | |
1.114 | CN | H | H | H | CN | CH | |
1.115 | CN | H | H | H | CN | CMe | |
1.116 | CN | H | H | H | CN | CCl | |
1.117 | CN | H | Me | H | CN | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.118 | CN | OH | H | Me | CN | CH | |
1.119 | CN | Me | H | H | CN | CH | |
1.120 | CN | OMe | H | H | CN | CH | |
1.121 | CN | H | H | H | OCF2H | N | |
1.122 | CN | H | H | H | OCF2H | CH | |
1.123 | CN | H | H | H | OCF2H | CMe | |
1.124 | CN | H | H | H | OCF2H | CCl | |
1.125 | CN | H | Me | H | OCF2H | CH | |
1.126 | CN | OH | H | Me | OCF2H | CH | |
1.127 | CN | Me | H | H | OCF2H | CH | |
1.128 | CN | OMe | H | H | OCF2H | CH | |
1.129 | CN | H | H | H | CN | N | |
1.130 | CN | H | H | H | CN | CH | |
1.131 | CN | H | H | H | CN | CMe | |
1.132 | CN | H | H | H | CN | CCl | |
1.133 | CN | H | Me | H | CN | CH | |
1.134 | CN | OH | H | Me | CN | CH | |
1.135 | CN | Me | H | H | CN | CH | |
1.136 | CN | OMe | H | H | CN | CH | |
1.137 | CN | H | H | H | CN | N | |
1.138 | CN | H | H | H | CN | CH | |
1.139 | CN | H | H | H | CN | CMe | |
1.140 | CN | H | H | H | CN | CCl | |
1.141 | CN | H | Me | H | CN | CH | |
1.142 | CN | OH | H | Me | CN | CH | |
1.143 | CN | Me | H | H | CN | CH | |
1.144 | CN | OMe | H | H | CN | CH | |
1.145 | OMe | H | H | H | CF3 | N | |
1.146 | OMe | H | H | H | CF3 | CH | |
1.147 | OMe | H | H | H | CF3 | CMe | |
1.148 | OMe | H | H | H | CF3 | CCl | |
1.149 | OMe | H | Me | H | CF3 | CH | |
1.150 | OMe | OH | H | Me | CF3 | CH | |
1.151 | OMe | Me | H | H | CF3 | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.152 | OMe | OMe | H | H | CF3 | CH | |
1.153 | OMe | H | H | H | Cl | N | |
1.154 | OMe | H | H | H | Cl | CH | |
1.155 | OMe | H | H | H | Cl | CMe | |
1.156 | OMe | H | H | H | Cl | CCl | |
1.157 | OMe | H | Me | H | Cl | CH | |
1.158 | OMe | OH | H | Me | Cl | CH | |
1.159 | OMe | Me | H | H | Cl | CH | |
1.160 | OMe | OMe | H | H | Cl | CH | |
1.161 | OMe | H | H | H | CN | N | |
1.162 | OMe | H | H | H | CN | CH | |
1.163 | OMe | H | H | H | CN | CMe | |
1.164 | OMe | H | H | H | CN | CCl | |
1.165 | OMe | H | Me | H | CN | CH | |
1.166 | OMe | OH | H | Me | CN | CH | |
1.167 | OMe | Me | H | H | CN | CH | |
1.168 | OMe | OMe | H | H | CN | CH | |
1.169 | OMe | H | H | H | OCF2H | N | |
1.170 | OMe | H | H | H | OCF2H | CH | |
1.171 | OMe | H | H | H | OCF2H | CMe | |
1.172 | OMe | H | H | H | OCF2H | CCl | |
1.173 | OMe | H | Me | H | OCF2H | CH | |
1.174 | OMe | OH | H | Me | OCF2H | CH | |
1.175 | OMe | Me | H | H | OCF2H | CH | |
1.176 | OMe | OMe | H | H | OCF2H | CH | |
1.177 | OMe | H | H | H | CN | N | |
1.178 | OMe | H | H | H | CN | CH | |
1.179 | OMe | H | H | H | CN | CMe | |
1.180 | OMe | H | H | H | CN | CCl | |
1.181 | OMe | H | Me | H | CN | CH | |
1.182 | OMe | OH | H | Me | CN | CH | |
1.183 | OMe | Me | H | H | CN | CH | |
1.184 | OMe | OMe | H | H | CN | CH | |
1.185 | OMe | H | H | H | CN | N |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
1.186 | OMe | H | H | H | CN | CH | |
1.187 | OMe | H | H | H | CN | CMe | |
1.188 | OMe | H | H | H | CN | CCl | |
1.189 | OMe | H | Me | H | CN | CH | |
1.190 | OMe | OH | H | Me | CN | CH | |
1.191 | OMe | Me | H | H | CN | CH | |
1.192 | OMe | OMe | H | H | CN | CH | |
1.193 | H | OMe | H | H | CF3 | N | m.p.100-102℃ |
1.194 | H | Cl | H | H | CF3 | N | m.p.91-93℃ |
1.195 | H | Me | Me | H | CF3 | N | m.p.97-99℃ |
表2:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y2 R6=H
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.1 | H | H | H | H | CF3 | N | |
2.2 | H | H | H | H | CF3 | CH | m.p.73-74℃ |
2.3 | H | H | H | H | CF3 | CMe | |
2.4 | H | H | H | H | CF3 | CCl | |
2.5 | H | H | Me | H | CF3 | CH | m.p.73-75℃ |
2.6 | H | OH | H | Me | CF3 | CH | |
2.7 | H | Me | H | H | CF3 | N | 1H NMR:δ[CDCl3]2.40(s,3H),7.50(dd,1H),7.70(d,1H),7.95(s,1H),8.50(s,1H),8.60(s,1H),8.85(d,1H). |
2.8 | H | OMe | H | H | CF3 | CH | |
2.9 | H | H | H | H | Cl | N | |
2.10 | H | H | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.11 | H | H | H | H | Cl | CMe | |
2.12 | H | H | H | H | Cl | CCl | |
2.13 | H | H | Me | H | Cl | CH | |
2.14 | H | OH | H | Me | Cl | CH | |
2.15 | H | Me | H | H | Cl | CH | |
2.16 | H | OMe | H | H | Cl | CH | |
2.17 | H | H | H | H | CN | N | |
2.18 | H | H | H | H | CN | CH | |
2.19 | H | H | H | H | CN | CMe | |
2.20 | H | H | H | H | CN | CCl | |
2.21 | H | H | Me | H | CN | CH | |
2.22 | H | OH | H | Me | CN | CH | |
2.23 | H | Me | H | H | CN | CH | |
2.24 | H | OMe | H | H | CN | CH | |
2.25 | H | H | H | H | OCF2H | N | |
2.26 | H | H | H | H | OCF2H | CH | |
2.27 | H | H | H | H | OCF2H | CMe | |
2.28 | H | H | H | H | OCF2H | CCl | |
2.29 | H | H | Me | H | OCF2H | CH | |
2.30 | H | OH | H | Me | OCF2H | CH | |
2.31 | H | Me | H | H | OCF2H | CH | |
2.32 | H | OMe | H | H | OCF2H | CH | |
2.33 | H | H | H | H | CN | N | |
2.34 | H | H | H | H | CN | CH | |
2.35 | H | H | H | H | CN | CMe | |
2.36 | H | H | H | H | CN | CCl | |
2.37 | H | H | Me | H | CN | CH | |
2.38 | H | OH | H | Me | CN | CH | |
2.39 | H | Me | H | H | CN | CH | |
2.40 | H | OMe | H | H | CN | CH | |
2.41 | H | H | H | H | CN | N | |
2.42 | H | H | H | H | CN | CH | |
2.43 | H | H | H | H | CN | CMe | |
2.44 | H | H | H | H | CN | CCl |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.45 | H | H | Me | H | CN | CH | |
2.46 | H | OH | H | Me | CN | CH | |
2.47 | H | Me | H | H | CN | CH | |
2.48 | H | OMe | H | H | CN | CH | |
2.49 | Me | H | H | H | CF3 | N | |
2.50 | Me | H | H | H | CF3 | CH | |
2.51 | Me | H | H | H | CF3 | CMe | |
2.52 | Me | H | H | H | CF3 | CCl | |
2.53 | Me | H | Me | H | CF3 | CH | |
2.54 | Me | OH | H | Me | CF3 | CH | |
2.55 | Me | Me | H | H | CF3 | CH | |
2.56 | Me | OMe | H | H | CF3 | CH | |
2.57 | Me | H | H | H | Cl | N | |
2.58 | Me | H | H | H | Cl | CH | |
2.59 | Me | H | H | H | Cl | CMe | |
2.60 | Me | H | H | H | Cl | CCl | |
2.61 | Me | H | Me | H | Cl | CH | |
2.62 | Me | OH | H | Me | Cl | CH | |
2.63 | Me | Me | H | H | Cl | CH | |
2.64 | Me | OMe | H | H | Cl | CH | |
2.65 | Me | H | H | H | CN | N | |
2.66 | Me | H | H | H | CN | CH | |
2.67 | Me | H | H | H | CN | CMe | |
2.68 | Me | H | H | H | CN | CCl | |
2.69 | Me | H | Me | H | CN | CH | |
2.70 | Me | OH | H | Me | CN | CH | |
2.71 | Me | Me | H | H | CN | CH | |
2.72 | Me | OMe | H | H | CN | CH | |
2.73 | Me | H | H | H | OCF2H | N | |
2.74 | Me | H | H | H | OCF2H | CH | |
2.75 | Me | H | H | H | OCF2H | CMe | |
2.76 | Me | H | H | H | OCF2H | CCl | |
2.77 | Me | H | Me | H | OCF2H | CH | |
2.78 | Me | OH | H | Me | OCF2H | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.79 | Me | Me | H | H | OCF2H | CH | |
2.80 | Me | OMe | H | H | OCF2H | CH | |
2.81 | Me | H | H | H | CN | N | |
2.82 | Me | H | H | H | CN | CH | |
2.83 | Me | H | H | H | CN | CMe | |
2.84 | Me | H | H | H | CN | CCl | |
2.85 | Me | H | Me | H | CN | CH | |
2.86 | Me | OH | H | Me | CN | CH | |
2.87 | Me | Me | H | H | CN | CH | |
2.88 | Me | OMe | H | H | CN | CH | |
2.89 | Me | H | H | H | CN | N | |
2.90 | Me | H | H | H | CN | CH | |
2.91 | Me | H | H | H | CN | CMe | |
2.92 | Me | H | H | H | CN | CCl | |
2.93 | Me | H | Me | H | CN | CH | |
2.94 | Me | OH | H | Me | CN | CH | |
2.95 | Me | Me | H | H | CN | CH | |
2.96 | Me | OMe | H | H | CN | CH | |
2.97 | CN | H | H | H | CF3 | N | m.p.115-116℃ |
2.98 | CN | H | H | H | CF3 | CH | |
2.99 | CN | H | H | H | CF3 | CMe | |
2.100 | CN | H | H | H | CF3 | CCl | |
2.101 | CN | H | Me | H | CF3 | CH | |
2.102 | CN | OH | H | Me | CF3 | CH | |
2.103 | CN | Me | H | H | CF3 | CH | |
2.104 | CN | OMe | H | H | CF3 | CH | |
2.105 | CN | H | H | H | Cl | N | |
2.106 | CN | H | H | H | Cl | CH | |
2.107 | CN | H | H | H | Cl | CMe | |
2.108 | CN | H | H | H | Cl | CCl | |
2.109 | CN | H | Me | H | Cl | CH | |
2.110 | CN | OH | H | Me | Cl | CH | |
2.111 | CN | Me | H | H | Cl | CH | |
2.112 | CN | OMe | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.113 | CN | H | H | H | CN | N | |
2.114 | CN | H | H | H | CN | CH | |
2.115 | CN | H | H | H | CN | CMe | |
2.116 | CN | H | H | H | CN | CCl | |
2.117 | CN | H | Me | H | CN | CH | |
2.118 | CN | OH | H | Me | CN | CH | |
2.119 | CN | Me | H | H | CN | CH | |
2.120 | CN | OMe | H | H | CN | CH | |
2.121 | CN | H | H | H | OCF2H | N | |
2.122 | CN | H | H | H | OCF2H | CH | |
2.123 | CN | H | H | H | OCF2H | CMe | |
2.124 | CN | H | H | H | OCF2H | CCl | |
2.125 | CN | H | Me | H | OCF2H | CH | |
2.126 | CN | OH | H | Me | OCF2H | CH | |
2.127 | CN | Me | H | H | OCF2H | CH | |
2.128 | CN | OMe | H | H | OCF2H | CH | |
2.129 | CN | H | H | H | CN | N | |
2.130 | CN | H | H | H | CN | CH | |
2.131 | CN | H | H | H | CN | CMe | |
2.132 | CN | H | H | H | CN | CCl | |
2.133 | CN | H | Me | H | CN | CH | |
2.134 | CN | OH | H | Me | CN | CH | |
2.135 | CN | Me | H | H | CN | CH | |
2.136 | CN | OMe | H | H | CN | CH | |
2.137 | CN | H | H | H | CN | N | |
2.138 | CN | H | H | H | CN | CH | |
2.139 | CN | H | H | H | CN | CMe | |
2.140 | CN | H | H | H | CN | CCl | |
2.141 | CN | H | Me | H | CN | CH | |
2.142 | CN | OH | H | Me | CN | CH | |
2.143 | CN | Me | H | H | CN | CH | |
2.144 | CN | OMe | H | H | CN | CH | |
2.145 | OMe | H | H | H | CF3 | N | |
2.146 | OMe | H | H | H | CF3 | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.147 | OMe | H | H | H | CF3 | CMe | |
2.148 | OMe | H | H | H | CF3 | CCl | |
2.149 | OMe | H | Me | H | CF3 | CH | |
2.150 | OMe | OH | H | Me | CF3 | CH | |
2.151 | OMe | Me | H | H | CF3 | CH | |
2.152 | OMe | OMe | H | H | CF3 | CH | |
2.153 | OMe | H | H | H | Cl | N | |
2.154 | OMe | H | H | H | Cl | CH | |
2.155 | OMe | H | H | H | Cl | CMe | |
2.156 | OMe | H | H | H | C1 | CCl | |
2.157 | OMe | H | Me | H | Cl | CH | |
2.158 | OMe | OH | H | Me | Cl | CH | |
2.159 | OMe | Me | H | H | Cl | CH | |
2.160 | OMe | OMe | H | H | Cl | CH | |
2.161 | OMe | H | H | H | CN | N | |
2.162 | OMe | H | H | H | CN | CH | |
2.163 | OMe | H | H | H | CN | CMe | |
2.164 | OMe | H | H | H | CN | CCl | |
2.165 | OMe | H | Me | H | CN | CH | |
2.166 | OMe | OH | H | Me | CN | CH | |
2.167 | OMe | Me | H | H | CN | CH | |
2.168 | OMe | OMe | H | H | CN | CH | |
2.169 | OMe | H | H | H | OCF2H | N | |
2.170 | OMe | H | H | H | OCF2H | CH | |
2.171 | OMe | H | H | H | OCF2H | CMe | |
2.172 | OMe | H | H | H | OCF2H | CCl | |
2.173 | OMe | H | Me | H | OCF2H | CH | |
2.174 | OMe | OH | H | Me | OCF2H | CH | |
2.175 | OMe | Me | H | H | OCF2H | CH | |
2.176 | OMe | OMe | H | H | OCF2H | CH | |
2.177 | OMe | H | H | H | CN | N | |
2.178 | OMe | H | H | H | CN | CH | |
2.179 | OMe | H | H | H | CN | CMe | |
2.180 | OMe | H | H | H | CN | CCl |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
2.181 | OMe | H | Me | H | CN | CH | |
2.182 | OMe | OH | H | Me | CN | CH | |
2.183 | OMe | Me | H | H | CN | CH | |
2.184 | OMe | OMe | H | H | CN | CH | |
2.185 | OMe | H | H | H | CN | N | |
2.186 | OMe | H | H | H | CN | CH | |
2.187 | OMe | H | H | H | CN | CMe | |
2.188 | OMe | H | H | H | CN | CCl | |
2.189 | OMe | H | Me | H | CN | CH | |
2.190 | OMe | OH | H | Me | CN | CH | |
2.191 | OMe | Me | H | H | CN | CH | |
2.192 | OMe | OMe | H | H | CN | CH | |
2.193 | H | OMe | H | H | CF3 | N | m.p.137-139℃ |
2.194 | H | Br | H | H | CF3 | N | m.p.101-103℃ |
2.195 | H | Cl | H | H | CF3 | N | m.p.119-121℃ |
2.196 | H | Me | H | Me | CF3 | N | 1H-NMR:2.10(s,3H);2.40(s,3H);6.95(dd,1H);7.20(d,1H);7.75(s,1H);8.35(d,1H);8.60(s,1H) |
表3:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y3 R6=H
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.1 | H | H | H | H | CF3 | N | |
3.2 | H | H | H | H | CF3 | CH | |
3.3 | H | H | H | H | CF3 | CMe | |
3.4 | H | H | H | H | CF3 | CCl | |
3.5 | H | H | Me | H | CF3 | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.6 | H | OH | H | Me | CF3 | CH | |
3.7 | H | Me | H | H | CF3 | CH | |
3.8 | H | OMe | H | H | CF3 | CH | |
3.9 | H | H | H | H | Cl | N | |
3.10 | H | H | H | H | Cl | CH | |
3.11 | H | H | H | H | Cl | CMe | |
3.12 | H | H | H | H | Cl | CCl | |
3.13 | H | H | Me | H | Cl | CH | |
3.14 | H | OH | H | Me | Cl | CH | |
3.15 | H | Me | H | H | Cl | CH | |
3.16 | H | OMe | H | H | Cl | CH | |
3.17 | H | H | H | H | CN | N | |
3.18 | H | H | H | H | CN | CH | |
3.19 | H | H | H | H | CN | CMe | |
3.20 | H | H | H | H | CN | CCl | |
3.21 | H | H | Me | H | CN | CH | |
3.22 | H | OH | H | Me | CN | CH | |
3.23 | H | Me | H | H | CN | CH | |
3.24 | H | OMe | H | H | CN | CH | |
3.25 | H | H | H | H | OCF2H | N | |
3.26 | H | H | H | H | OCF2H | CH | |
3.27 | H | H | H | H | OCF2H | CMe | |
3.28 | H | H | H | H | OCF2H | CCl | |
3.29 | H | H | Me | H | OCF2H | CH | |
3.30 | H | OH | H | Me | OCF2H | CH | |
3.31 | H | Me | H | H | OCF2H | CH | |
3.32 | H | OMe | H | H | OCF2H | CH | |
3.33 | H | H | H | H | CN | N | |
3.34 | H | H | H | H | CN | CH | |
3.35 | H | H | H | H | CN | CMe | |
3.36 | H | H | H | H | CN | CCl | |
3.37 | H | H | Me | H | CN | CH | |
3.38 | H | OH | H | Me | CN | CH | |
3.39 | H | Me | H | H | CN | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.40 | H | OMe | H | H | CN | CH | |
3.41 | H | H | H | H | CN | N | |
3.42 | H | H | H | H | CN | CH | |
3.43 | H | H | H | H | CN | CMe | |
3.44 | H | H | H | H | CN | CCl | |
3.45 | H | H | Me | H | CN | CH | |
3.46 | H | OH | H | Me | CN | CH | |
3.47 | H | Me | H | H | CN | CH | |
3.48 | H | OMe | H | H | CN | CH | |
3.49 | Me | H | H | H | CF3 | N | |
3.50 | Me | H | H | H | CF3 | CH | |
3.51 | Me | H | H | H | CF3 | CMe | |
3.52 | Me | H | H | H | CF3 | CCl | |
3.53 | Me | H | Me | H | CF3 | CH | |
3.54 | Me | OH | H | Me | CF3 | CH | |
3.55 | Me | Me | H | H | CF3 | CH | |
3.56 | Me | OMe | H | H | CF3 | CH | |
3.57 | Me | H | H | H | Cl | N | |
3.58 | Me | H | H | H | Cl | CH | |
3.59 | Me | H | H | H | Cl | CMe | |
3.60 | Me | H | H | H | Cl | CCl | |
3.61 | Me | H | Me | H | Cl | CH | |
3.62 | Me | OH | H | Me | Cl | CH | |
3.63 | Me | Me | H | H | Cl | CH | |
3.64 | Me | OMe | H | H | Cl | CH | |
3.65 | Me | H | H | H | CN | N | |
3.66 | Me | H | H | H | CN | CH | |
3.67 | Me | H | H | H | CN | CMe | |
3.68 | Me | H | H | H | CN | CCl | |
3.69 | Me | H | Me | H | CN | CH | |
3.70 | Me | OH | H | Me | CN | CH | |
3.71 | Me | Me | H | H | CN | CH | |
3.72 | Me | OMe | H | H | CN | CH | |
3.73 | Me | H | H | H | OCF2H | N |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.74 | Me | H | H | H | OCF2H | CH | |
3.75 | Me | H | H | H | OCF2H | CMe | |
3.76 | Me | H | H | H | OCF2H | CCl | |
3.77 | Me | H | Me | H | OCF2H | CH | |
3.78 | Me | OH | H | Me | OCF2H | CH | |
3.79 | Me | Me | H | H | OCF2H | CH | |
3.80 | Me | OMe | H | H | OCF2H | CH | |
3.81 | Me | H | H | H | CN | N | |
3.82 | Me | H | H | H | CN | CH | |
3.83 | Me | H | H | H | CN | CMe | |
3.84 | Me | H | H | H | CN | CCl | |
3.85 | Me | H | Me | H | CN | CH | |
3.86 | Me | OH | H | Me | CN | CH | |
3.87 | Me | Me | H | H | CN | CH | |
3.88 | Me | OMe | H | H | CN | CH | |
3.89 | Me | H | H | H | CN | N | |
3.90 | Me | H | H | H | CN | CH | |
3.91 | Me | H | H | H | CN | CMe | |
3.92 | Me | H | H | H | CN | CCl | |
3.93 | Me | H | Me | H | CN | CH | |
3.94 | Me | OH | H | Me | CN | CH | |
3.95 | Me | Me | H | H | CN | CH | |
3.96 | Me | OMe | H | H | CN | CH | |
3.97 | CN | H | H | H | CF3 | N | |
3.98 | CN | H | H | H | CF3 | CH | |
3.99 | CN | H | H | H | CF3 | CMe | |
3.100 | CN | H | H | H | CF3 | CCl | |
3.101 | CN | H | Me | H | CF3 | CH | |
3.102 | CN | OH | H | Me | CF3 | CH | |
3.103 | CN | Me | H | H | CF3 | CH | |
3.104 | CN | OMe | H | H | CF3 | CH | |
3.105 | CN | H | H | H | Cl | N | |
3.106 | CN | H | H | H | Cl | CH | |
3.107 | CN | H | H | H | Cl | CMe |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.108 | CN | H | H | H | Cl | CCl | |
3.109 | CN | H | Me | H | Cl | CH | |
3.110 | CN | OH | H | Me | Cl | CH | |
3.111 | CN | Me | H | H | Cl | CH | |
3.112 | CN | OMe | H | H | Cl | CH | |
3.113 | CN | H | H | H | CN | N | |
3.114 | CN | H | H | H | CN | CH | |
3.115 | CN | H | H | H | CN | CMe | |
3.116 | CN | H | H | H | CN | CCl | |
3.117 | CN | H | Me | H | CN | CH | |
3.118 | CN | OH | H | Me | CN | CH | |
3.119 | CN | Me | H | H | CN | CH | |
3.120 | CN | OMe | H | H | CN | CH | |
3.121 | CN | H | H | H | OCF2H | N | |
3.122 | CN | H | H | H | OCF2H | CH | |
3.123 | CN | H | H | H | OCF2H | CMe | |
3.124 | CN | H | H | H | OCF2H | CCl | |
3.125 | CN | H | Me | H | OCF2H | CH | |
3.126 | CN | OH | H | Me | OCF2H | CH | |
3.127 | CN | Me | H | H | OCF2H | CH | |
3.128 | CN | OMe | H | H | OCF2H | CH | |
3.129 | CN | H | H | H | CN | N | |
3.130 | CN | H | H | H | CN | CH | |
3.131 | CN | H | H | H | CN | CMe | |
3.132 | CN | H | H | H | CN | CCl | |
3.133 | CN | H | Me | H | CN | CH | |
3.134 | CN | OH | H | Me | CN | CH | |
3.135 | CN | Me | H | H | CN | CH | |
3.136 | CN | OMe | H | H | CN | CH | |
3.137 | CN | H | H | H | CN | N | |
3.138 | CN | H | H | H | CN | CH | |
3.139 | CN | H | H | H | CN | CMe | |
3.140 | CN | H | H | H | CN | CCl | |
3.141 | CN | H | Me | H | CN | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.142 | CN | OH | H | Me | CN | CH | |
3.143 | CN | Me | H | H | CN | CH | |
3.144 | CN | OMe | H | H | CN | CH | |
3.145 | OMe | H | H | H | CF3 | N | |
3.146 | OMe | H | H | H | CF3 | CH | |
3.147 | OMe | H | H | H | CF3 | CMe | |
3.148 | OMe | H | H | H | CF3 | CCl | |
3.149 | OMe | H | Me | H | CF3 | CH | |
3.150 | OMe | OH | H | Me | CF3 | CH | |
3.151 | OMe | Me | H | H | CF3 | CH | |
3.152 | OMe | OMe | H | H | CF3 | CH | |
3.153 | OMe | H | H | H | Cl | N | |
3.154 | OMe | H | H | H | Cl | CH | |
3.155 | OMe | H | H | H | Cl | CMe | |
3.156 | OMe | H | H | H | Cl | CCl | |
3.157 | OMe | H | Me | H | Cl | CH | |
3.158 | OMe | OH | H | Me | Cl | CH | |
3.159 | OMe | Me | H | H | Cl | CH | |
3.160 | OMe | OMe | H | H | Cl | CH | |
3.161 | OMe | H | H | H | CN | N | |
3.162 | OMe | H | H | H | CN | CH | |
3.163 | OMe | H | H | H | CN | CMe | |
3.164 | OMe | H | H | H | CN | CCl | |
3.165 | OMe | H | Me | H | CN | CH | |
3.166 | OMe | OH | H | Me | CN | CH | |
3.167 | OMe | Me | H | H | CN | CH | |
3.168 | OMe | OMe | H | H | CN | CH | |
3.169 | OMe | H | H | H | OCF2H | N | |
3.170 | OMe | H | H | H | OCF2H | CH | |
3.171 | OMe | H | H | H | OCF2H | CMe | |
3.172 | OMe | H | H | H | OCF2H | CCl | |
3.173 | OMe | H | Me | H | OCF2H | CH | |
3.174 | OMe | OH | H | Me | OCF2H | CH | |
3.175 | OMe | Me | H | H | OCF2H | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
3.176 | OMe | OMe | H | H | OCF2H | CH | |
3.177 | OMe | H | H | H | CN | N | |
3.178 | OMe | H | H | H | CN | CH | |
3.179 | OMe | H | H | H | CN | CMe | |
3.180 | OMe | H | H | H | CN | CCl | |
3.181 | OMe | H | Me | H | CN | CH | |
3.182 | OMe | OH | H | Me | CN | CH | |
3.183 | OMe | Me | H | H | CN | CH | |
3.184 | OMe | OMe | H | H | CN | CH | |
3.185 | OMe | H | H | H | CN | N | |
3.186 | OMe | H | H | H | CN | CH | |
3.187 | OMe | H | H | H | CN | CMe | |
3.188 | OMe | H | H | H | CN | CCl | |
3.189 | OMe | H | Me | H | CN | CH | |
3.190 | OMe | OH | H | Me | CN | CH | |
3.191 | OMe | Me | H | H | CN | CH | |
3.192 | OMe | OMe | H | H | CN | CH |
表4:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y4 R6=H R7=Me
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.1 | H | H | H | H | CF3 | N | 1HNMR:δ[CDCl3]3.82(s,3H),6.60(s,1H),7.05(d,1H),8.00(s,1H),8.65(s,1H),8.80(d,1H) |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.2 | H | H | H | H | CF3 | CH | 1H NMR(CDCl3/TMS):δ(ppm)=8.43(s,1H),7.97(t,1H),7.88(s,1H),7.82(d,1H),7.00(d,1H),6.34(s,1H),3.82(s,3H). |
4.3 | H | H | H | H | CF3 | CMe | |
4.4 | H | H | H | H | CF3 | CCl | |
4.5 | H | H | Me | H | CF3 | CH | m.p.95-96℃ |
4.6 | H | OH | H | Me | CF3 | CH | |
4.7 | H | Me | H | H | CF3 | CH | |
4.8 | H | OMe | H | H | CF3 | CH | |
4.9 | H | H | H | H | Cl | N | |
4.10 | H | H | H | H | Cl | CH | |
4.11 | H | H | H | H | C1 | CMe | |
4.12 | H | H | H | H | Cl | CCl | |
4.13 | H | H | Me | H | Cl | CH | |
4.14 | H | OH | H | Me | Cl | CH | |
4.15 | H | Me | H | H | Cl | CH | |
4.16 | H | OMe | H | H | Cl | CH | |
4.17 | H | H | H | H | CN | N | |
4.18 | H | H | H | H | CN | CH | |
4.19 | H | H | H | H | CN | CMe | |
4.20 | H | H | H | H | CN | CCl | |
4.2l | H | H | Me | H | CN | CH | |
4.22 | H | OH | H | Me | CN | CH | |
4.23 | H | Me | H | H | CN | CH | |
4.24 | H | OMe | H | H | CN | CH | |
4.25 | H | H | H | H | OCF2H | N | |
4.26 | H | H | H | H | OCF2H | CH | |
4.27 | H | H | H | H | OCF2H | CMe | |
4.28 | H | H | H | H | OCF2H | CCl | |
4.29 | H | H | Me | H | OCF2H | CH | |
4.30 | H | OH | H | Me | OCF2H | CH | |
4.31 | H | Me | H | H | OCF2H | CH | |
4.32 | H | OMe | H | H | OCF2H | CH | |
4.33 | H | H | H | H | CN | N |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.34 | H | H | H | H | CN | CH | |
4.35 | H | H | H | H | CN | CMe | |
4.36 | H | H | H | H | CN | CCl | |
4.37 | H | H | Me | H | CN | CH | |
4.38 | H | OH | H | Me | CN | CH | |
4.39 | H | Me | H | H | CN | CH | |
4.40 | H | OMe | H | H | CN | CH | |
4.41 | H | H | H | H | CN | N | |
4.42 | H | H | H | H | CN | CH | |
4.43 | H | H | H | H | CN | CMe | |
4.44 | H | H | H | H | CN | CCl | |
4.45 | H | H | Me | H | CN | CH | |
4.46 | H | OH | H | Me | CN | CH | |
4.47 | H | Me | H | H | CN | CH | |
4.48 | H | OMe | H | H | CN | CH | |
4.49 | Me | H | H | H | CF3 | N | m.p.122-124℃ |
4.50 | Me | H | H | H | CF3 | CH | 1H NMR(CDCl3/TMS):δ(ppm)8.43(s,1H),7.86(s,1H),7.67(s,1H),6.82(s,1H),6.30(s,1H),3.82(s,3H),2.50(s,3H). |
4.51 | Me | H | H | H | CF3 | CMe | |
4.52 | Me | H | H | H | CF3 | CCl | |
4.53 | Me | H | Me | H | CF3 | CH | |
4.54 | Me | OH | H | Me | CF3 | CH | |
4.55 | Me | Me | H | H | CF3 | CH | |
4.56 | Me | OMe | H | H | CF3 | CH | |
4.57 | Me | H | H | H | Cl | N | |
4.58 | Me | H | H | H | Cl | CH | |
4.59 | Me | H | H | H | Cl | CMe | |
4.60 | Me | H | H | H | Cl | CCl | |
4.61 | Me | H | Me | H | Cl | CH | |
4.62 | Me | OH | H | Me | Cl | CH | |
4.63 | Me | Me | H | H | Cl | CH | |
4.64 | Me | OMe | H | H | Cl | CH | |
4.65 | Me | H | H | H | CN | N |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.66 | Me | H | H | H | CN | CH | |
4.67 | Me | H | H | H | CN | CMe | |
4.68 | Me | H | H | H | CN | CCl | |
4.69 | Me | H | Me | H | CN | CH | |
4.70 | Me | OH | H | Me | CN | CH | |
4.71 | Me | Me | H | H | CN | CH | |
4.72 | Me | OMe | H | H | CN | CH | |
4.73 | Me | H | H | H | OCF2H | N | |
4.74 | Me | H | H | H | OCF2H | CH | |
4.75 | Me | H | H | H | OCF2H | CMe | |
4.76 | Me | H | H | H | OCF2H | CCl | |
4.77 | Me | H | Me | H | OCF2H | CH | |
4.78 | Me | OH | H | Me | OCF2H | CH | |
4.79 | Me | Me | H | H | OCF2H | CH | |
4.80 | Me | OMe | H | H | OCF2H | CH | |
4.81 | Me | H | H | H | CN | N | |
4.82 | Me | H | H | H | CN | CH | |
4.83 | Me | H | H | H | CN | CMe | |
4.84 | Me | H | H | H | CN | CCl | |
4.85 | Me | H | Me | H | CN | CH | |
4.86 | Me | OH | H | Me | CN | CH | |
4.87 | Me | Me | H | H | CN | CH | |
4.88 | Me | OMe | H | H | CN | CH | |
4.89 | Me | H | H | H | CN | N | |
4.90 | Me | H | H | H | CN | CH | |
4.91 | Me | H | H | H | CN | CMe | |
4.92 | Me | H | H | H | CN | CCl | |
4.93 | Me | H | Me | H | CN | CH | |
4.94 | Me | OH | H | Me | CN | CH | |
4.95 | Me | Me | H | H | CN | CH | |
4.96 | Me | OMe | H | H | CN | CH | |
4.97 | CN | H | H | H | CF3 | N | |
4.98 | CN | H | H | H | CF3 | CH | Rf=0.63;庚烷/乙酸乙酯1∶1 |
4.99 | CN | H | H | H | CF3 | CMe |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.100 | CN | H | H | H | CF3 | CCl | |
4.101 | CN | H | Me | H | CF3 | CH | 1H NMR[CDCl3]:2.42(s,3H);3.86(s,3H);6.36(s,1H);7.19(s,1H);8.02(s,1H);8.30(s,1H) |
4.102 | CN | OH | H | Me | CF3 | CH | |
4.103 | CN | Me | H | H | CF3 | CH | |
4.104 | CN | OMe | H | H | CF3 | CH | |
4.105 | CN | H | H | H | Cl | N | |
4.106 | CN | H | H | H | Cl | CH | |
4.107 | CN | H | H | H | Cl | CMe | |
4.108 | CN | H | H | H | Cl | CCl | |
4.109 | CN | H | Me | H | Cl | CH | |
4.110 | CN | OH | H | Me | Cl | CH | |
4.111 | CN | Me | H | H | Cl | CH | |
4.112 | CN | OMe | H | H | Cl | CH | |
4.113 | CN | H | H | H | CN | N | |
4.114 | CN | H | H | H | CN | CH | |
4.115 | CN | H | H | H | CN | CMe | |
4.116 | CN | H | H | H | CN | CCl | |
4.117 | CN | H | Me | H | CN | CH | |
4.118 | CN | OH | H | Me | CN | CH | |
4.119 | CN | Me | H | H | CN | CH | |
4.120 | CN | OMe | H | H | CN | CH | |
4.121 | CN | H | H | H | OCF2H | N | |
4.122 | CN | H | H | H | OCF2H | CH | |
4.123 | CN | H | H | H | OCF2H | CMe | |
4.124 | CN | H | H | H | OCF2H | CCl | |
4.125 | CN | H | Me | H | OCF2H | CH | |
4.126 | CN | OH | H | Me | OCF2H | CH | |
4.127 | CN | Me | H | H | OCF2H | CH | |
4.128 | CN | OMe | H | H | OCF2H | CH | |
4.129 | CN | H | H | H | CN | N | |
4.130 | CN | H | H | H | CN | CH | |
4.131 | CN | H | H | H | CN | CMe | |
4.132 | CN | H | H | H | CN | CCl |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.133 | CN | H | Me | H | CN | CH | |
4.134 | CN | OH | H | Me | CN | CH | |
4.135 | CN | Me | H | H | CN | CH | |
4.136 | CN | OMe | H | H | CN | CH | |
4.137 | CN | H | H | H | CN | N | |
4.138 | CN | H | H | H | CN | CH | |
4.139 | CN | H | H | H | CN | CMe | |
4.140 | CN | H | H | H | CN | CCl | |
4.141 | CN | H | Me | H | CN | CH | |
4.142 | CN | OH | H | Me | CN | CH | |
4.143 | CN | Me | H | H | CN | CH | |
4.144 | CN | OMe | H | H | CN | CH | |
4.145 | OMe | H | H | H | CF3 | N | |
4.146 | OMe | H | H | H | CF3 | CH | 1H NMR(CDCl3/TMS):δ(ppm)8.42(s,1H),7.85(s,1H),7.40(d,1H),6.44(d,1H,),6.29(s,1H),3.99(s,3H),3.81(s,3H). |
4.147 | OMe | H | H | H | CF3 | CMe | |
4.148 | OMe | H | H | H | CF3 | CCl | |
4.149 | OMe | H | Me | H | CF3 | CH | |
4.150 | OMe | OH | H | Me | CF3 | CH | |
4.151 | OMe | Me | H | H | CF3 | CH | |
4.152 | OMe | OMe | H | H | CF3 | CH | |
4.153 | OMe | H | H | H | Cl | N | |
4.154 | OMe | H | H | H | Cl | CH | |
4.155 | OMe | H | H | H | Cl | CMe | |
4.156 | OMe | H | H | H | Cl | CCl | |
4.157 | OMe | H | Me | H | Cl | CH | |
4.158 | OMe | OH | H | Me | Cl | CH | |
4.159 | OMe | Me | H | H | Cl | CH | |
4.160 | OMe | OMe | H | H | Cl | CH | |
4.161 | OMe | H | H | H | CN | N | |
4.162 | OMe | H | H | H | CN | CH | |
4.163 | OMe | H | H | H | CN | CMe | |
4.164 | OMe | H | H | H | CN | CCl |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
4.165 | OMe | H | Me | H | CN | CH | |
4.166 | OMe | OH | H | Me | CN | CH | |
4.167 | OMe | Me | H | H | CN | CH | |
4.168 | OMe | OMe | H | H | CN | CH | |
4.169 | OMe | H | H | H | OCF2H | N | |
4.170 | OMe | H | H | H | OCF2H | CH | |
4.171 | OMe | H | H | H | OCF2H | CMe | |
4.172 | OMe | H | H | H | OCF2H | CCl | |
4.173 | OMe | H | Me | H | OCF2H | CH | |
4.174 | OMe | OH | H | Me | OCF2H | CH | |
4.175 | OMe | Me | H | H | OCF2H | CH | |
4.176 | OMe | OMe | H | H | OCF2H | CH | |
4.177 | OMe | H | H | H | CN | N | |
4.178 | OMe | H | H | H | CN | CH | |
4.179 | OMe | H | H | H | CN | CMe | |
4.180 | OMe | H | H | H | CN | CCl | |
4.181 | OMe | H | Me | H | CN | CH | |
4.182 | OMe | OH | H | Me | CN | CH | |
4.183 | OMe | Me | H | H | CN | CH | |
4.184 | OMe | OMe | H | H | CN | CH | |
4.185 | OMe | H | H | H | CN | N | |
4.186 | OMe | H | H | H | CN | CH | |
4.187 | OMe | H | H | H | CN | CMe | |
4.188 | OMe | H | H | H | CN | CCl | |
4.189 | OMe | H | Me | H | CN | CH | |
4.190 | OMe | OH | H | Me | CN | CH | |
4.191 | OMe | Me | H | H | CN | CH | |
4.192 | OMe | OMe | H | H | CN | CH | |
4.193 | H | Cl | H | H | CF3 | N | m.p.113-115℃ |
4.194 | Et | H | H | H | CF3 | N | m.p.106-108℃ |
4.195 | Et | H | Me | H | CF3 | N | m.p.121-123℃ |
4.196 | Et | H | H | Me | CF3 | N | 1H NMR[CDCl3]:1.40(t,3H);2.95(9,2H);2.50(s,3H);3.80(s,3H);6.45(s,1H);6.90(s,1H);7.88(s,1H) |
表5:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y4 R6=H R7=Me
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.1 | H | H | H | H | CF3 | N | |
5.2 | H | H | H | H | CF3 | CH | |
5.3 | H | H | H | H | CF3 | CMe | |
5.4 | H | H | H | H | CF3 | CCl | |
5.5 | H | H | Me | H | CF3 | CH | |
5.6 | H | OH | H | Me | CF3 | CH | |
5.7 | H | Me | H | H | CF3 | CH | |
5.8 | H | OMe | H | H | CF3 | CH | |
5.9 | H | H | H | H | Cl | N | |
5.10 | H | H | H | H | Cl | CH | |
5.11 | H | H | H | H | Cl | CMe | |
5.12 | H | H | H | H | Cl | CCl | |
5.13 | H | H | Me | H | Cl | CH | |
5.14 | H | OH | H | Me | Cl | CH | |
5.15 | H | Me | H | H | Cl | CH | |
5.16 | H | OMe | H | H | Cl | CH | |
5.17 | H | H | H | H | CN | N | |
5.18 | H | H | H | H | CN | CH | |
5.19 | H | H | H | H | CN | CMe | |
5.20 | H | H | H | H | CN | CCl | |
5.21 | H | H | Me | H | CN | CH | |
5.22 | H | OH | H | Me | CN | CH | |
5.23 | H | Me | H | H | CN | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.24 | H | OMe | H | H | CN | CH | |
5.25 | H | H | H | H | OCF2H | N | |
5.26 | H | H | H | H | OCF2H | CH | |
5.27 | H | H | H | H | OCF2H | CMe | |
5.28 | H | H | H | H | OCF2H | CCl | |
5.29 | H | H | Me | H | OCF2H | CH | |
5.30 | H | OH | H | Me | OCF2H | CH | |
5.31 | H | Me | H | H | OCF2H | CH | |
5.32 | H | OMe | H | H | OCF2H | CH | |
5.33 | H | H | H | H | CN | N | |
5.34 | H | H | H | H | CN | CH | |
5.35 | H | H | H | H | CN | CMe | |
5.36 | H | H | H | H | CN | CCl | |
5.37 | H | H | Me | H | CN | CH | |
5.38 | H | OH | H | Me | CN | CH | |
5.39 | H | Me | H | H | CN | CH | |
5.40 | H | OMe | H | H | CN | CH | |
5.41 | H | H | H | H | CN | N | |
5.42 | H | H | H | H | CN | CH | |
5.43 | H | H | H | H | CN | CMe | |
5.44 | H | H | H | H | CN | CCl | |
5.45 | H | H | Me | H | CN | CH | |
5.46 | H | OH | H | Me | CN | CH | |
5.47 | H | Me | H | H | CN | CH | |
5.48 | H | OMe | H | H | CN | CH | |
5.49 | Me | H | H | H | CF3 | N | |
5.50 | Me | H | H | H | CF3 | CH | |
5.51 | Me | H | H | H | CF3 | CMe | |
5.52 | Me | H | H | H | CF3 | CCl | |
5.53 | Me | H | Me | H | CF3 | CH | |
5.54 | Me | OH | H | Me | CF3 | CH | |
5.55 | Me | Me | H | H | CF3 | CH | |
5.56 | Me | OMe | H | H | CF3 | CH | |
5.57 | Me | H | H | H | Cl | N |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.58 | Me | H | H | H | Cl | CH | |
5.59 | Me | H | H | H | Cl | CMe | |
5.60 | Me | H | H | H | Cl | CCl | |
5.61 | Me | H | Me | H | Cl | CH | |
5.62 | Me | OH | H | Me | Cl | CH | |
5.63 | Me | Me | H | H | Cl | CH | |
5.64 | Me | OMe | H | H | Cl | CH | |
5.65 | Me | H | H | H | CN | N | |
5.66 | Me | H | H | H | CN | CH | |
5.67 | Me | H | H | H | CN | CMe | |
5.68 | Me | H | H | H | CN | CCl | |
5.69 | Me | H | Me | H | CN | CH | |
5.70 | Me | OH | H | Me | CN | CH | |
5.71 | Me | Me | H | H | CN | CH | |
5.72 | Me | OMe | H | H | CN | CH | |
5.73 | Me | H | H | H | OCF2H | N | |
5.74 | Me | H | H | H | OCF2H | CH | |
5.75 | Me | H | H | H | OCF2H | CMe | |
5.76 | Me | H | H | H | OCF2H | CCl | |
5.77 | Me | H | Me | H | OCF2H | CH | |
5.78 | Me | OH | H | Me | OCF2H | CH | |
5.79 | Me | Me | H | H | OCF2H | CH | |
5.80 | Me | OMe | H | H | OCF2H | CH | |
5.81 | Me | H | H | H | CN | N | |
5.82 | Me | H | H | H | CN | CH | |
5.83 | Me | H | H | H | CN | CMe | |
5.84 | Me | H | H | H | CN | CCl | |
5.85 | Me | H | Me | H | CN | CH | |
5.86 | Me | OH | H | Me | CN | CH | |
5.87 | Me | Me | H | H | CN | CH | |
5.88 | Me | OMe | H | H | CN | CH | |
5.89 | Me | H | H | H | CN | N | |
5.90 | Me | H | H | H | CN | CH | |
5.91 | Me | H | H | H | CN | CMe |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.92 | Me | H | H | H | CN | CCl | |
5.93 | Me | H | Me | H | CN | CH | |
5.94 | Me | OH | H | Me | CN | CH | |
5.95 | Me | Me | H | H | CN | CH | |
5.96 | Me | OMe | H | H | CN | CH | |
5.97 | CN | H | H | H | CF3 | N | |
5.98 | CN | H | H | H | CF3 | CH | |
5.99 | CN | H | H | H | CF3 | CMe | |
5.100 | CN | H | H | H | CF3 | CCl | |
5.101 | CN | H | Me | H | CF3 | CH | |
5.102 | CN | OH | H | Me | CF3 | CH | |
5.103 | CN | Me | H | H | CF3 | CH | |
5.104 | CN | OMe | H | H | CF3 | CH | |
5.105 | CN | H | H | H | Cl | N | |
5.106 | CN | H | H | H | Cl | CH | |
5.107 | CN | H | H | H | Cl | CMe | |
5.108 | CN | H | H | H | Cl | CCl | |
5.109 | CN | H | Me | H | Cl | CH | |
5.110 | CN | OH | H | Me | Cl | CH | |
5.111 | CN | Me | H | H | Cl | CH | |
5.112 | CN | OMe | H | H | Cl | CH | |
5.113 | CN | H | H | H | CN | N | |
5.114 | CN | H | H | H | CN | CH | |
5.115 | CN | H | H | H | CN | CMe | |
5.116 | CN | H | H | H | CN | CCl | |
5.117 | CN | H | Me | H | CN | CH | |
5.118 | CN | OH | H | Me | CN | CH | |
5.119 | CN | Me | H | H | CN | CH | |
5.120 | CN | OMe | H | H | CN | CH | |
5.121 | CN | H | H | H | OCF2H | N | |
5.122 | CN | H | H | H | OCF2H | CH | |
5.123 | CN | H | H | H | OCF2H | CMe | |
5.124 | CN | H | H | H | OCF2H | CCl | |
5.125 | CN | H | Me | H | OCF2H | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.126 | CN | OH | H | Me | OCF2H | CH | |
5.127 | CN | Me | H | H | OCF2H | CH | |
5.128 | CN | OMe | H | H | OCF2H | CH | |
5.129 | CN | H | H | H | CN | N | |
5.130 | CN | H | H | H | CN | CH | |
5.131 | CN | H | H | H | CN | CMe | |
5.132 | CN | H | H | H | CN | CCl | |
5.133 | CN | H | Me | H | CN | CH | |
5.134 | CN | OH | H | Me | CN | CH | |
5.135 | CN | Me | H | H | CN | CH | |
5.136 | CN | OMe | H | H | CN | CH | |
5.137 | CN | H | H | H | CN | N | |
5.138 | CN | H | H | H | CN | CH | |
5.139 | CN | H | H | H | CN | CMe | |
5.140 | CN | H | H | H | CN | CCl | |
5.141 | CN | H | Me | H | CN | CH | |
5.142 | CN | OH | H | Me | CN | CH | |
5.143 | CN | Me | H | H | CN | CH | |
5.144 | CN | OMe | H | H | CN | CH | |
5.145 | OMe | H | H | H | CF3 | N | |
5.146 | OMe | H | H | H | CF3 | CH | |
5.147 | OMe | H | H | H | CF3 | CMe | |
5.148 | OMe | H | H | H | CF3 | CCl | |
5.149 | OMe | H | Me | H | CF3 | CH | |
5.150 | OMe | OH | H | Me | CF3 | CH | |
5.151 | OMe | Me | H | H | CF3 | CH | |
5.152 | OMe | OMe | H | H | CF3 | CH | |
5.153 | OMe | H | H | H | C1 | N | |
5.154 | OMe | H | H | H | Cl | CH | |
5.155 | OMe | H | H | H | Cl | CMe | |
5.156 | OMe | H | H | H | Cl | CCl | |
5.157 | OMe | H | Me | H | Cl | CH | |
5.158 | OMe | OH | H | Me | Cl | CH | |
5.159 | OMe | Me | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
5.160 | OMe | OMe | H | H | Cl | CH | |
5.161 | OMe | H | H | H | CN | N | |
5.162 | OMe | H | H | H | CN | CH | |
5.163 | OMe | H | H | H | CN | CMe | |
5.164 | OMe | H | H | H | CN | CCl | |
5.165 | OMe | H | Me | H | CN | CH | |
5.166 | OMe | OH | H | Me | CN | CH | |
5.167 | OMe | Me | H | H | CN | CH | |
5.168 | OMe | OMe | H | H | CN | CH | |
5.169 | OMe | H | H | H | OCF2H | N | |
5.170 | OMe | H | H | H | OCF2H | CH | |
5.171 | OMe | H | H | H | OCF2H | CMe | |
5.172 | OMe | H | H | H | OCF2H | CCl | |
5.173 | OMe | H | Me | H | OCF2H | CH | |
5.174 | OMe | OH | H | Me | OCF2H | CH | |
5.175 | OMe | Me | H | H | OCF2H | CH | |
5.176 | OMe | OMe | H | H | OCF2H | CH | |
5.177 | OMe | H | H | H | CN | N | |
5.178 | OMe | H | H | H | CN | CH | |
5.179 | OMe | H | H | H | CN | CMe | |
5.180 | OMe | H | H | H | CN | CCl | |
5.181 | OMe | H | Me | H | CN | CH | |
5.182 | OMe | OH | H | Me | CN | CH | |
5.183 | OMe | Me | H | H | CN | CH | |
5.184 | OMe | OMe | H | H | CN | CH | |
5.185 | OMe | H | H | H | CN | N | |
5.186 | OMe | H | H | H | CN | CH | |
5.187 | OMe | H | H | H | CN | CMe | |
5.188 | OMe | H | H | H | CN | CCl | |
5.189 | OMe | H | Me | H | CN | CH | |
5.190 | OMe | OH | H | Me | CN | CH | |
5.191 | OMe | Me | H | H | CN | CH | |
5.192 | OMe | OMe | H | H | CN | CH |
表6:本发明式(I)化合物,其中取代基和符号如下所定义:
Y=Y6 R6=H R7=Me
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.1 | H | H | H | H | CF3 | N | |
6.2 | H | H | H | H | CF3 | CH | |
6.3 | H | H | H | H | CF3 | CMe | |
6.4 | H | H | H | H | CF3 | CCl | |
6.5 | H | H | Me | H | CF3 | CH | |
6.6 | H | OH | H | Me | CF3 | CH | |
6.7 | H | Me | H | H | CF3 | CH | |
6.8 | H | OMe | H | H | CF3 | CH | |
6.9 | H | H | H | H | Cl | N | |
6.10 | H | H | H | H | Cl | CH | |
6.11 | H | H | H | H | Cl | CMe | |
6.12 | H | H | H | H | Cl | CCl | |
6.13 | H | H | Me | H | Cl | CH | |
6.14 | H | OH | H | Me | Cl | CH | |
6.15 | H | Me | H | H | Cl | CH | |
6.16 | H | OMe | H | H | Cl | CH | |
6.17 | H | H | H | H | CN | N | |
6.18 | H | H | H | H | CN | CH | |
6.19 | H | H | H | H | CN | CMe | |
6.20 | H | H | H | H | CN | CCl | |
6.21 | H | H | Me | H | CN | CH | |
6.22 | H | OH | H | Me | CN | CH | |
6.23 | H | Me | H | H | CN | CH | |
6.24 | H | OMe | H | H | CN | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.25 | H | H | H | H | OCF2H | N | |
6.26 | H | H | H | H | OCF2H | CH | |
6.27 | H | H | H | H | OCF2H | CMe | |
6.28 | H | H | H | H | OCF2H | CCl | |
6.29 | H | H | Me | H | OCF2H | CH | |
6.30 | H | OH | H | Me | OCF2H | CH | |
6.31 | H | Me | H | H | OCF2H | CH | |
6.32 | H | OMe | H | H | OCF2H | CH | |
6.33 | H | H | H | H | CN | N | |
6.34 | H | H | H | H | CN | CH | |
6.35 | H | H | H | H | CN | CMe | |
6.36 | H | H | H | H | CN | CCl | |
6.37 | H | H | Me | H | CN | CH | |
6.38 | H | OH | H | Me | CN | CH | |
6.39 | H | Me | H | H | CN | CH | |
6.40 | H | OMe | H | H | CN | CH | |
6.41 | H | H | H | H | CN | N | |
6.42 | H | H | H | H | CN | CH | |
6.43 | H | H | H | H | CN | CMe | |
6.44 | H | H | H | H | CN | CCl | |
6.45 | H | H | Me | H | CN | CH | |
6.46 | H | OH | H | Me | CN | CH | |
6.47 | H | Me | H | H | CN | CH | |
6.48 | H | OMe | H | H | CN | CH | |
6.49 | Me | H | H | H | CF3 | N | |
6.50 | Me | H | H | H | CF3 | CH | |
6.51 | Me | H | H | H | CF3 | CMe | |
6.52 | Me | H | H | H | CF3 | CCl | |
6.53 | Me | H | Me | H | CF3 | CH | |
6.54 | Me | OH | H | Me | CF3 | CH | |
6.55 | Me | Me | H | H | CF3 | CH | |
6.56 | Me | OMe | H | H | CF3 | CH | |
6.57 | Me | H | H | H | Cl | N | |
6.58 | Me | H | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.59 | Me | H | H | H | Cl | CMe | |
6.60 | Me | H | H | H | Cl | CCl | |
6.61 | Me | H | Me | H | Cl | CH | |
6.62 | Me | OH | H | Me | Cl | CH | |
6.63 | Me | Me | H | H | Cl | CH | |
6.64 | Me | OMe | H | H | Cl | CH | |
6.65 | Me | H | H | H | CN | N | |
6.66 | Me | H | H | H | CN | CH | |
6.67 | Me | H | H | H | CN | CMe | |
6.68 | Me | H | H | H | CN | CCl | |
6.69 | Me | H | Me | H | CN | CH | |
6.70 | Me | OH | H | Me | CN | CH | |
6.71 | Me | Me | H | H | CN | CH | |
6.72 | Me | OMe | H | H | CN | CH | |
6.73 | Me | H | H | H | OCF2H | N | |
6.74 | Me | H | H | H | OCF2H | CH | |
6.75 | Me | H | H | H | OCF2H | CMe | |
6.76 | Me | H | H | H | OCF2H | CCl | |
6.77 | Me | H | Me | H | OCF2H | CH | |
6.78 | Me | OH | H | Me | OCF2H | CH | |
6.79 | Me | Me | H | H | OCF2H | CH | |
6.80 | Me | OMe | H | H | OCF2H | CH | |
6.81 | Me | H | H | H | CN | N | |
6.82 | Me | H | H | H | CN | CH | |
6.83 | Me | H | H | H | CN | CMe | |
6.84 | Me | H | H | H | CN | CCl | |
6.85 | Me | H | Me | H | CN | CH | |
6.86 | Me | OH | H | Me | CN | CH | |
6.87 | Me | Me | H | H | CN | CH | |
6.88 | Me | OMe | H | H | CN | CH | |
6.89 | Me | H | H | H | CN | N | |
6.90 | Me | H | H | H | CN | CH | |
6.91 | Me | H | H | H | CN | CMe | |
6.92 | Me | H | H | H | CN | CCl |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.93 | Me | H | Me | H | CN | CH | |
6.94 | Me | OH | H | Me | CN | CH | |
6.95 | Me | Me | H | H | CN | CH | |
6.96 | Me | OMe | H | H | CN | CH | |
6.97 | CN | H | H | H | CF3 | N | |
6.98 | CN | H | H | H | CF3 | CH | |
6.99 | CN | H | H | H | CF3 | CMe | |
6.100 | CN | H | H | H | CF3 | CCl | |
6.101 | CN | H | Me | H | CF3 | CH | |
6.102 | CN | OH | H | Me | CF3 | CH | |
6.103 | CN | Me | H | H | CF3 | CH | |
6.104 | CN | OMe | H | H | CF3 | CH | |
6.105 | CN | H | H | H | Cl | N | |
6.106 | CN | H | H | H | Cl | CH | |
6.107 | CN | H | H | H | Cl | CMe | |
6.108 | CN | H | H | H | Cl | CCl | |
6.109 | CN | H | Me | H | Cl | CH | |
6.110 | CN | OH | H | Me | Cl | CH | |
6.111 | CN | Me | H | H | Cl | CH | |
6.112 | CN | OMe | H | H | Cl | CH | |
6.113 | CN | H | H | H | CN | N | |
6.114 | CN | H | H | H | CN | CH | |
6.115 | CN | H | H | H | CN | CMe | |
6.116 | CN | H | H | H | CN | CCl | |
6.117 | CN | H | Me | H | CN | CH | |
6.118 | CN | OH | H | Me | CN | CH | |
6.119 | CN | Me | H | H | CN | CH | |
6.120 | CN | OMe | H | H | CN | CH | |
6.121 | CN | H | H | H | OCF2H | N | |
6.122 | CN | H | H | H | OCF2H | CH | |
6.123 | CN | H | H | H | OCF2H | CMe | |
6.124 | CN | H | H | H | OCF2H | CCl | |
6.125 | CN | H | Me | H | OCF2H | CH | |
6.126 | CN | OH | H | Me | OCF2H | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.127 | CN | Me | H | H | OCF2H | CH | |
6.128 | CN | OMe | H | H | OCF2H | CH | |
6.129 | CN | H | H | H | CN | N | |
6.130 | CN | H | H | H | CN | CH | |
6.131 | CN | H | H | H | CN | CMe | |
6.132 | CN | H | H | H | CN | CCl | |
6.133 | CN | H | Me | H | CN | CH | |
6.134 | CN | OH | H | Me | CN | CH | |
6.135 | CN | Me | H | H | CN | CH | |
6.136 | CN | OMe | H | H | CN | CH | |
6.137 | CN | H | H | H | CN | N | |
6.138 | CN | H | H | H | CN | CH | |
6.139 | CN | H | H | H | CN | CMe | |
6.140 | CN | H | H | H | CN | CCl | |
6.141 | CN | H | Me | H | CN | CH | |
6.142 | CN | OH | H | Me | CN | CH | |
6.143 | CN | Me | H | H | CN | CH | |
6.144 | CN | OMe | H | H | CN | CH | |
6.145 | OMe | H | H | H | CF3 | N | |
6.146 | OMe | H | H | H | CF3 | CH | |
6.147 | OMe | H | H | H | CF3 | CMe | |
6.148 | OMe | H | H | H | CF3 | CCl | |
6.149 | OMe | H | Me | H | CF3 | CH | |
6.150 | OMe | OH | H | Me | CF3 | CH | |
6.151 | OMe | Me | H | H | CF3 | CH | |
6.152 | OMe | OMe | H | H | CF3 | CH | |
6.153 | OMe | H | H | H | Cl | N | |
6.154 | OMe | H | H | H | C1 | CH | |
6.155 | OMe | H | H | H | Cl | CMe | |
6.156 | OMe | H | H | H | Cl | CCl | |
6.157 | OMe | H | Me | H | Cl | CH | |
6.158 | OMe | OH | H | Me | Cl | CH | |
6.159 | OMe | Me | H | H | Cl | CH | |
6.160 | OMe | OMe | H | H | Cl | CH |
No. | R1 | R2 | R3 | R4 | R5 | Z | 物理数据 |
6.161 | OMe | H | H | H | CN | N | |
6.162 | OMe | H | H | H | CN | CH | |
6.163 | OMe | H | H | H | CN | CMe | |
6.164 | OMe | H | H | H | CN | CCl | |
6.165 | OMe | H | Me | H | CN | CH | |
6.166 | OMe | OH | H | Me | CN | CH | |
6.167 | OMe | Me | H | H | CN | CH | |
6.168 | OMe | OMe | H | H | CN | CH | |
6.169 | OMe | H | H | H | OCF2H | N | |
6.170 | OMe | H | H | H | OCF2H | CH | |
6.171 | OMe | H | H | H | OCF2H | CMe | |
6.172 | OMe | H | H | H | OCF2H | CCl | |
6.173 | OMe | H | Me | H | OCF2H | CH | |
6.174 | OMe | OH | H | Me | OCF2H | CH | |
6.175 | OMe | Me | H | H | OCF2H | CH | |
6.176 | OMe | OMe | H | H | OCF2H | CH | |
6.177 | OMe | H | H | H | CN | N | |
6.178 | OMe | H | H | H | CN | CH | |
6.179 | OMe | H | H | H | CN | CMe | |
6.180 | OMe | H | H | H | CN | CCl | |
6.181 | OMe | H | Me | H | CN | CH | |
6.182 | OMe | OH | H | Me | CN | CH | |
6.183 | OMe | Me | H | H | CN | CH | |
6.184 | OMe | OMe | H | H | CN | CH | |
6.185 | OMe | H | H | H | CN | N | |
6.186 | OMe | H | H | H | CN | CH | |
6.187 | OMe | H | H | H | CN | CMe | |
6.188 | OMe | H | H | H | CN | CCl | |
6.189 | OMe | H | Me | H | CN | CH | |
6.190 | OMe | OH | H | Me | CN | CH | |
6.191 | OMe | Me | H | H | CN | CH | |
6.192 | OMe | OMe | H | H | CN | CH |
B.制剂实施例
1.粉剂
粉剂的制备是将10重量份的式(I)化合物与90重量份的滑石(作为惰性物质)加以混合,将该混合物在锤磨机中粉碎。
2.可分散粉剂
在水中易于分散的可湿性粉剂的制备是将25重量份的式(I)化合物,64重量份的含高岭土的石英(作为惰性物质),10重量份的木质磺酸钾和1重量份的油酰甲基牛磺酸钠(作为润湿剂和分散剂)加以混合,将该混合物在栓型碟式磨粉机上研磨该混合物。
3.分散性浓缩物
在水中易于分散的分散性浓缩物的制备是将20重量份的式(I)化合物、6重量份的烷基酚聚乙二醇醚(Triton X 207)、3重量份的异十三烷醇聚乙二醇醚(8 EO)和71重量份的链烷烃矿物油(沸点范围约255至277℃以上)加以混合,并且在球磨机上研磨该混合物至小于5微米的细度。
4.乳油
乳油是由下列物质组成:15重量份的式(I)化合物,75重量份的环己酮作为溶剂和10重量份的氧乙基化的壬酚作为乳化剂。
5.水分散颗粒剂
水分散颗粒剂是利用下列方式制得:将
75重量份的式(I)化合物,
10重量份的木质磺酸钙,
5重量份的月桂硫酸钠,
3重量份的聚乙烯醇和
7重量份的高岭土
加以混合,将该混合物在栓型碟式磨粉机中磨成细粉,将粉末在流体化床中通过喷洒作为粒化液体的水以使之粒化。
水分散颗粒剂也可通过于胶体磨上将下列物质均质化且预先粉碎
25重量份的式(I)化合物,
5重量份的2,2′-二萘基甲烷-6,6′-二磺酸钠,
2重量份的油酰甲基牛磺酸钠,
1重量份的聚乙烯醇,
17重量份的碳酸钙和
50重量份的水,
随后将该混合物在球磨机中磨成细粉,在喷雾塔中利用单物质喷嘴将如此得到的悬浮体加以雾化和干燥。
C.生物实施例
1.对杂草植物的除草活性和作物的耐受性,苗前试验
将单子叶和双子叶杂草植物和作物的种子置于硬纸盒中的砂壤土中并覆上土壤。随后在600~800公升水/公顷的施用量下(经换算),将以可湿性粉剂或乳油形式配制的本发明化合物以不同水量的水悬浮液或乳液形式施加至土壤表面。处理之后,将硬纸盒置于温室中并保持适于杂草的良好生长条件。试验进行3至4周后,在待试植物出苗后,与未处理对照相比,目测评价对植物或苗的损害。在该实施例中,例如来自实施例号1.7和4.1的本发明化合物以320g活性物质/公顷的施用量显示了控制下列杂草100%的活性:马唐、狗尾草和短苞反枝苋。本发明该化合物同样的施用量对作物糯稻(水稻)和Glycine max(大豆)却无损害。来自实施例号1.7的本发明化合物以20g活性物质/公顷的施用量显示了控制下列杂草至少90%的活性:大穗看麦娘、狗尾草、短苞反枝苋和阿拉伯婆婆纳。该化合物同样的施用量对作物糯稻(水稻)、玉蜀黍(玉米)和Glycine max(大豆)却无损害。来自实施例号4.146的本发明化合物以320g活性物质/公顷的施用量显示了控制下列杂草100%的活性:短苞反枝苋、狗尾草和繁缕。
2.对杂草植物的除草活性和作物的耐受性,苗后试验
将单子叶和双子叶杂草植物和作物的种子置于硬纸盒中的砂壤土中并覆上土壤,并于温室中在良好的生长条件下培养。播种2至3周后,在三叶阶段时处理试验植物。随后在600~800公升水/公顷的施用量下(经换算),将以可湿性粉剂或乳油形式配制的本发明化合物以不同水量施加至植物绿色部分。将试验植物置于理想的生长条件下的温室中3至4周后,记录化合物的活性。该实施例中,例如来自实施例号4.1和4.49号的本发明化合物以80g活性物质/公顷的施用量显示控制下列杂草至少90%的活性:狗尾草、马唐、母菊、短苞反枝苋、牵牛、藜、阿拉伯婆婆纳和苘麻。
Claims (15)
1.一种式(I)化合物,或其N-氧化物或其盐,
其中基团和符号如下定义:
Z为N或CR8;
Y为Y1至Y7的基团:
R1和R2分别独立地为氢、卤素、氰基、异氰基、OH、COOR10、COR10、CH2OH、CH2SH、CH2NH2、NO2、CSNH2、CONH2、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基、(C1-C2)-烷氧基-(C1-C2)-烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C3-C4)-烯氧基、(C3-C4)-炔氧基、(C1-C2)-烷硫基-(C1-C2)-烷基、S(O)nR9、(C1-C2)-烷基磺酰基-(C1-C2)-烷基、氨基、(C1-C4)-烷基氨基、(C1-C3)-烷基羰基氨基、(C1-C4)-烷基磺酰基氨基或二-(C1-C4)-烷基氨基;
R3和R4分别独立地为氢、卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基或卤代-(C1-C4)-烷氧基;
R5为卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基、卤代-(C1-C4)-烷硫基、(C3-C5)-环烷基、卤代-(C3-C5)-环烷基、SF5、S(O)nR9、(C2-C4)-烯基或(C2-C4)-炔基;
R6为氢、卤素、氰基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、(C1-C4)-烷氧基、卤代-(C1-C4)-烷氧基或S(O)nR9;
R7为(C1-C4)-烷基;
R8为氢、卤素、氰基、NO2、(C1-C4)-烷基、(C1-C4)-烷氧基、羟基、氨基、(C1-C4)-烷基氨基、(C1-C3)-烷基羰基氨基、(C1-C4)-烷基磺酰基氨基、二-(C1-C4)-烷基氨基或S(O)nR9;
R9为氢、(C1-C4)-烷基或卤代-(C1-C4)-烷基;
R10为氢或(C1-C4)-烷基;
n为0,1或2。
2.根据权利要求1的化合物,其特征在于Y为Y1至Y6的基团。
3.根据权利要求1或2的化合物,其特征在于R1和R2分别为氢、卤素、氰基、OH、CHO、乙烯基、(C1-C4)-烷基、卤代-(C1-C4)-烷基、乙烯基或(C1-C4)-烷氧基。
4.根据权利要求1至3任一所述的化合物,其特征在于R3和R4分别为氢、卤素、甲基或甲氧基。
5.根据权利要求1至4任一所述的化合物,其特征在于
R1为氢、卤素、氰基、CHO、甲氧基、甲基或乙基,并且
R2为氢、OH、甲基、乙基、甲氧基或乙氧基。
6.根据权利要求1至5任一所述的化合物,其特征在于R3和R4分别为氢或甲基。
7.根据权利要求1至6任一所述的化合物,其特征在于R8为氢、卤素或(C1-C4)-烷基。
8.根据权利要求1至7任一所述的化合物,其特征在于R5为氢、氰基、卤代-(C1-C4)-烷基、卤代-(C1-C4)-烷氧基或卤代-(C1-C4)-烷硫基。
9.根据权利要求1至8任一所述的化合物,其特征在于R6为氢。
10.一种包含除草有效量的至少一种权利要求1至9任一所述的式(I)化合物的除草组合物。
11.根据权利要求10的除草组合物,其特征在于为具有助剂的混合物形式。
12.一种用于控制不需要植物的方法,其特征在于将有效量的至少一种如权利要求1至9任一所述的式(I)化合物或如权利要求10或11所述的除草组合物施用至植物或不需要植物生长的场所。
13.将如权利要求1至9任一所述的式(I)化合物或如权利要求10或11所述的除草组合物用于控制不需要植物的用途。
14.根据权利要求13的用途,其特征在于将式(I)化合物用于控制有用作物中的不需要的植物。
15.根据权利要求14的用途,其中有用植物是转基因的。
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BR9815453A (pt) * | 1997-03-11 | 2001-10-23 | Du Pont | Composto, composição herbicida e método para controle do crescimento de vegetação indesejada |
CA2309260C (en) * | 1997-12-03 | 2011-09-13 | E.I. Du Pont De Nemours And Company | 2,4-substituted pyrimidines and their use in herbicidal compositions |
CA2326020A1 (en) * | 1999-11-17 | 2001-05-17 | Basf Corporation | Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines |
US20040198758A1 (en) | 2001-08-17 | 2004-10-07 | Rapado Liliana Parra | N-heterocyclyl substituted thienyloxy-pyrimidines used as herbicides |
-
2002
- 2002-07-25 DE DE10234876A patent/DE10234876A1/de not_active Withdrawn
-
2003
- 2003-07-14 EP EP03740461A patent/EP1527067B1/de not_active Expired - Lifetime
- 2003-07-14 DK DK03740461T patent/DK1527067T3/da active
- 2003-07-14 MX MXPA05000954A patent/MXPA05000954A/es active IP Right Grant
- 2003-07-14 CA CA002493749A patent/CA2493749A1/en not_active Abandoned
- 2003-07-14 AT AT03740461T patent/ATE341546T1/de not_active IP Right Cessation
- 2003-07-14 WO PCT/EP2003/007574 patent/WO2004013129A1/de active IP Right Grant
- 2003-07-14 CN CNA038175975A patent/CN1671698A/zh active Pending
- 2003-07-14 AU AU2003281853A patent/AU2003281853A1/en not_active Abandoned
- 2003-07-14 BR BR0312915-2A patent/BR0312915A/pt not_active IP Right Cessation
- 2003-07-14 UA UAA200501725A patent/UA80149C2/uk unknown
- 2003-07-14 PL PL03375395A patent/PL375395A1/xx not_active Application Discontinuation
- 2003-07-14 RS YUP-2005/0030A patent/RS20050030A/sr unknown
- 2003-07-14 ES ES03740461T patent/ES2273013T3/es not_active Expired - Lifetime
- 2003-07-14 DE DE50305279T patent/DE50305279D1/de not_active Expired - Fee Related
- 2003-07-14 PT PT03740461T patent/PT1527067E/pt unknown
- 2003-07-14 RU RU2005105574/04A patent/RU2005105574A/ru not_active Application Discontinuation
- 2003-07-14 JP JP2004525189A patent/JP2006505513A/ja not_active Abandoned
- 2003-07-23 TW TW092120034A patent/TW200403026A/zh unknown
- 2003-07-23 AR AR20030102639A patent/AR040667A1/es not_active Application Discontinuation
- 2003-07-24 MY MYPI20032797A patent/MY130697A/en unknown
- 2003-07-24 US US10/627,256 patent/US7282469B2/en not_active Expired - Fee Related
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2005
- 2005-01-24 HR HR20050074A patent/HRP20050074A2/hr not_active Application Discontinuation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114349704A (zh) * | 2022-01-21 | 2022-04-15 | 河南师范大学 | 三氟甲基缀合的吡唑螺环丙烷类化合物及其合成方法 |
Also Published As
Publication number | Publication date |
---|---|
AR040667A1 (es) | 2005-04-13 |
PT1527067E (pt) | 2007-01-31 |
MY130697A (en) | 2007-07-31 |
ATE341546T1 (de) | 2006-10-15 |
BR0312915A (pt) | 2005-07-12 |
AU2003281853A1 (en) | 2004-02-23 |
CA2493749A1 (en) | 2004-02-12 |
MXPA05000954A (es) | 2005-05-16 |
WO2004013129A1 (de) | 2004-02-12 |
RU2005105574A (ru) | 2005-07-20 |
DK1527067T3 (da) | 2007-02-05 |
PL375395A1 (en) | 2005-11-28 |
DE50305279D1 (de) | 2006-11-16 |
DE10234876A1 (de) | 2004-02-05 |
EP1527067B1 (de) | 2006-10-04 |
UA80149C2 (en) | 2007-08-27 |
EP1527067A1 (de) | 2005-05-04 |
HRP20050074A2 (en) | 2006-03-31 |
ES2273013T3 (es) | 2007-05-01 |
TW200403026A (en) | 2004-03-01 |
JP2006505513A (ja) | 2006-02-16 |
RS20050030A (en) | 2007-09-21 |
US20040082475A1 (en) | 2004-04-29 |
US7282469B2 (en) | 2007-10-16 |
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