CN1659160A - 吡唑甲酰胺杀虫剂 - Google Patents
吡唑甲酰胺杀虫剂 Download PDFInfo
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- CN1659160A CN1659160A CN038127318A CN03812731A CN1659160A CN 1659160 A CN1659160 A CN 1659160A CN 038127318 A CN038127318 A CN 038127318A CN 03812731 A CN03812731 A CN 03812731A CN 1659160 A CN1659160 A CN 1659160A
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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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- 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
- C07D401/14—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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明提供了式(I)化合物、其N-氧化物或其盐,其中:A是O或S;B是苯环或吡啶环,各环任选被1-5个R取代J是本发明定义的吡唑或吡咯杂环系;R1是H;或各自任选被一个或多个取代基取代的C1-C6烷基、C2-C6烯基、C2-C6炔基或C3-C6环烷基,所述取代基选自:卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基。本发明还公开了一种防治至少一种无脊椎动物害虫的方法,包括将无脊椎动物害虫或其环境与至少一种生物有效量式(I)化合物、其N-氧化物或其盐(例如,以本发明描述的组合物的形式)接触。本发明还涉及一种组合物,其含有至少一种式(I)化合物、其N-氧化物或其盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其它组分。
Description
发明背景
本发明涉及某些杂环酰胺类化合物、其N-氧化物、盐和其适用于农艺和非农艺用途(包括下文列举的那些用途)的组合物及其在农艺和非农艺环境中用于防治无脊椎动物害虫的方法。
为了得到高农作物效率,防治无脊椎动物害虫极为重要。无脊椎动物害虫对生长和贮藏的农艺作物所造成的损害可导致生产率显著下降,并进而导致消费者的费用增加。在林业、温室作物、观赏植物、苗圃作物、存储的食物和纤维产品、家畜、家庭及公共和动物健康各方面防治无脊椎动物害虫也是重要的。用于这些目的的许多产品可从市场购得,但仍需要更有效的、更低成本、更低毒性、对环境安全或具有不同作用模式的新化合物。
JP02129171公开了式i的N-吡唑甲酰苯胺衍生物作为杀虫剂,
其中,R1-R3和X1-R5的定义同本发明。
发明概述
本发明涉及式I化合物、其N-氧化物或其盐,
其中,
A是O或S;
B是苯环或吡啶环,各环被1-5个R2取代;
J是选自J-1、J-2、J-3、J-4、J-5和J-6的吡唑或吡咯杂环系;
R1是H;或各自任选被一个或多个取代基任意取代的C1-C6烷基、C2-C6烯基、C2-C6炔基或C3-C6环烷基,所述取代基选自:卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
R1是C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
各个R2独立地选自:H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C2-C4氰基烷基、卤素、CN、NO2、哌啶、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚硫酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
各个R2独立地选自:苯基环、苄基环或苯氧基环,各个环任选被一个或多个取代基取代,所述取代基选自:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C4-C7(烷基)环烷基氨基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C3-C8二烷基氨基羰基;
R5是
各个R6、R6a和R7独立地选自:H、C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基和C1-C4卤代烷硫基;和
R8是H、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C1-C4卤代烷氧基。
本发明还涉及防治至少一种无脊椎动物害虫的方法,该方法包括将所述无脊椎动物害虫或其环境与至少一种生物有效量式I化合物、其N-氧化物或其盐(例如,以本发明描述的组合物的形式)接触。本发明还涉及这样一种方法,其中,将无脊椎动物害虫或其环境与至少一种生物有效量式I化合物、其N-氧化物或其盐接触,或与生物有效量组合物接触,所述组合物含有至少一种式I化合物、其N-氧化物或其盐和至少一种用于防治无脊椎动物害虫的其它生物有效量生物活性化合物或试剂。
本发明还涉及一种组合物,其含有至少一种式I化合物、其N-氧化物或其盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其它组分。本发明还涉及一种含有至少一种式I化合物、其N-氧化物或其盐和至少一种其它生物活性化合物或试剂的组合物。
发明详述
在上文描述中,术语“烷基”,单独使用或以诸如“烷硫基”或“卤代烷基”的复合词形式使用,包括直链或支链烷基,例如,甲基、乙基、正丙基、异丙基或不同的丁基、戊基或己基异构体。“烯基”包括直链或支链烯基,例如,乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体。“烯基”还包括多烯基,例如,1,2-丙二烯基和2,4-己二烯基。“炔基”包括直链或支链炔基,例如,乙炔基、1-丙炔基、2-丙炔基和不同的丁炔基、戊炔基和己炔基异构体。“炔基”还可以包括由多个三键构成的基团,例如,2,5-己二炔基。“烷氧基”包括,例如,甲氧基、乙氧基、正丙氧基、异丙氧基和不同的丁氧基、戊氧基和己氧基异构体。“烷硫基”包括直链或支链烷硫基,例如,甲硫基、乙硫基和不同的丙硫基和丁硫基异构体。“烷基亚硫酰基”包括烷基亚硫酰基的两种对映体。“烷基亚硫酰基”的实例包括CH3S(O)、CH3CH2S(O)、CH3CH2CH2S(O)、(CH3)2CHS(O)和不同的丁基亚硫酰基异构体。“烷基磺酰基”的实例包括CH3S(O)2、CH3CH2S(O)2、CH3CH2CH2S(O)2、(CH3)2CHS(O)2和不同的丁基磺酰基异构体。“氰基烷基”是指被一个氰基取代的烷基。“氰基烷基”的实例包括NCCH2、NCCH2CH2和CH3CH(CN)CH2。“烷基氨基”、“二烷基氨基”等的定义类似于上述实例。“环烷基”包括,例如,环丙基、环丁基、环戊基和环己基。术语“环烷基氨基”包括经氮原子进行连接的上述基团,例如,环戊基氨基和环己氨基。
有关环或环系的术语“杂”指至少一个环原子不是碳且可含有1-4个独立地选自氮、氧和硫杂原子的环或环系,其条件是,各个环含有不超过4个氮原子、不超过2个氧原子和不超过2个硫原子。术语“杂芳环或环系”和“芳香稠合杂双环系”是指全芳香杂环和其中多核环系的至少一个环呈芳香性(此处芳香性是指满足休克尔法则)的杂环。所述杂环或环系可以通过任何合适的碳或氮、通过取代所述碳或氮上的氢进行连接。
术语“卤素”,单独使用或以诸如“卤代烷基”复合词的形式使用,包括氟、氯、溴或碘。而且,当以诸如“卤代烷基”或“卤代环烷基”的复合词形式使用时,所述烷基或环烷基可以被相同或不同的卤原子部分或全部取代。“卤代烷基”的实例包括F3C、ClCH2、CF3CH2和CF3CCl2。术语“卤代烯基”、“卤代炔基”、“卤代烷氧基”或“卤代烷硫基”等的定义类似于术语“卤代烷基”。“卤代烯基”的实例包括(Cl)2C=CHCH2和CF3CH2CH=CHCH2。“卤代炔基”的实例包括HC≡CCHCl、CF3C≡C、CCl3C≡C和FCH2C≡CCH2。“卤代烷氧基”的实例包括CF3O、CCl3CH2O、HCF2CH2CH2O和CF3CH2O。“卤代烷硫基”的实例包括CCl3S、CF3S、CCl3CH2S和ClCH2CH2CH2S。“卤代烷基亚硫酰基”的实例包括CF3S(O)、CCl3S(O)、CF3CH2S(O)和CF3CF2S(O)。“卤代烷基磺酰基”的实例包括CF3S(O)2、CCl3S(O)2、CF3CH2S(O)2和CF3CF2S(O)2。
“烷基羰基”的实例包括C(O)CH3、C(O)CH2CH2CH3和C(O)CH(CH3)2。“烷氧基羰基”的实例包括CH3OC(=O)、CH3CH2OC(=O)、CH3CH2CH2OC(=O)、(CH3)2CHOC(=O)和不同的丁氧基-或戊氧基羰基异构体。“烷基氨基羰基”的实例包括CH3NHC(=O)、CH3CH2NHC(=O)、CH3CH2CH2NHC(=O)、(CH3)2CHNHC(=O)和不同的丁基氨基-或戊基氨基羰基异构体。“二烷基氨基羰基”的实例包括(CH3)2NC(=O)、(CH3CH2)2NC(=O)、CH3CH2(CH3)NC(=O)、CH3CH2CH2(CH3)NC(=O)和(CH3)2CHN(CH3)C(=O)。
取代基中的碳原子总数用“Ci-Cj”前缀表示,其中i和j是1-8的数。例如,C1-C3烷基磺酰基表示甲磺酰基至丙磺酰基;C2烷氧基烷基表示CH3OCH2;C3烷氧基烷基表示,例如,CH3CH(OCH3)、CH3OCH2CH2或CH3CH2OCH2;和C4烷氧基烷基表示被烷氧基取代的各种烷基异构体,其碳原子总数为4,其实例包括CH3CH2CH2OCH2和CH3CH2OCH2CH2。
在上文描述中,当式I化合物由一个或多个杂环组成时,所有取代基经任何合适的碳或氮并通过取代所述碳或氮上的氢连接至这些环上。
当化合物被带有下标的取代基取代时(下标表明所述取代基的数目可以超过1),所述取代基(当超过1时)独立地选自所定义的取代基。而且,当下标表示一个范围时,例如,(R)i-j,则取代基数目可选自i和j之间的整数,包括i和j。
“任选被1-3个取代基取代”之类的术语表示可以在基团的1-3个合适位置上进行取代。当基团含有可以为氢的取代基(如,R1或R5)时,那么,如果该取代基是氢,则此时相当于所述基团未被取代。
本发明化合物可以以一种或多种立体异构体的形式存在。备种立体异构体包括对映体、非对映体、阻转异构体和几何异构体。本领域技术人员知道,当相对于其它立体异构体而言富含一种立体异构体时,或者,当一种立体异构体与其它立体异构体分开时,该立体异构体可能更具有活性和/或可以表现出有益效应。另外,本领域技术人员懂得如何分离、富集和/或选择性制备所述立体异构体。因此,本发明包括式I化合物、其N-氧化物和其盐。本发明化合物可以是立体异构体混合物、单一立体异构体或以光学活性形式存在。
本领域技术人员知道,并非所有的含氮杂环都能形成N-氧化物,这是因为,为了氧化形成氧化物,氮需要有效的孤对电子;本领域技术人员能够识别那些能形成N-氧化物的含氮杂环。本领域技术人员还公认叔胺能形成N-氧化物。用于制备杂环和叔胺的N-氧化物的合成方法是本领域技术人员众所周知的,包括用过氧酸(如,过乙酸和间-氯过苯甲酸(MCPBA))、过氧化氢、烷基氢过氧化物(如,叔丁基氢过氧化物)、过硼酸钠和二环氧乙烷(如,二甲基二环氧乙烷)氧化杂环和叔胺。文献中已彻底描述和评论了这些N-氧化物制备方法,例如,参见:T.L.Gilchristin Comprehensive Organic Synthesis,vol.7,pp 748-750,S.V.Ley,Ed.,Pergamon Press;M.Tisler andB.Stanovnik in Comprehensive Heterocyclic Chemistry,vol.3,pp18-20,A.J.Boulton and A.McKillop,Eds.,Pergamon Press;M.R.Grimmett and B.R.T.Keene in Advances in HeterocyclicChemistry,vol.43,pp149-161,A.R.Katritzky,Ed.,AcademicPress;M.Tisler and B.Stanovnikin Advances in HeterocyclicChemistry,vol.9,pp285-291,A.R.Katritzky and A.J.Boulton,Eds.,Academic Press;和G.W.H.Cheeseman and E.S.G.Werstiukin Advances in Heterocyclic Chemistry,vol.22,pp390-392,A.R.Katritzky and A.J.Boulton,Eds.,Academic Press。
本发明化合物的盐包括与诸如氢溴酸、盐酸、硝酸、磷酸、硫酸、乙酸、丁酸、富马酸、乳酸、马来酸、丙二酸、乙二酸、丙酸、水杨酸、酒石酸、4-甲苯磺酸或戊酸的无机或有机酸形成的酸加成盐。当化合物含有诸如羧酸或酚的酸性基团时,本发明化合物的盐还包括与有机碱(例如,吡啶、氨或三乙胺)或无机碱(例如,钠、钾、锂、钙、镁或钡的氢化物、氢氧化物或碳酸盐)形成的盐。在本发明的组合物和方法中,本发明化合物的盐优选适用于本发明描述的农艺和/或非农艺用途。
如上所述,B是苯环或吡啶环,各个环被1-5个R2取代。所述的被1-5个R2取代的B环的实例包括下图1中B-1-B-4所示的环系,其中,n是1-5的整数和R2定义同上。需要指出的是,B基团可以仅被少于5个R2基团取代(例如,B-2-B-4可以仅被4个R2取代)。
图1
优选的B环是任选被取代的苯基。
值得注意的是式I化合物是这样的式I化合物,其中
A是O或S;
B是苯环或吡啶环,各个环被1-5个R2取代;
J是选自J-1、J-2、J-3、J-4、J-5和J-6的吡唑或吡咯杂环系;
R1是H;或各自任选被一个或多个取代基取代的C1-C6烷基、C2-C6烯基、C2-C6炔基或C3-C6环烷基,所述取代基选自:卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
R1是C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
各个R2独立地选自:H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C2-C4氰基烷基、卤素、CN、NO2、哌啶、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚硫酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
各个R2独立地选自:苯基环、苄基环或苯氧基环,各个环任选被一个或多个取代基取代,所述取代基选自:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C4-C7(烷基)环烷基氨基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C3-C8二烷基氨基羰基;
R5是
各个R6和R7独立地选自:H、C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基和C1-C4卤代烷硫基;和
R8是H、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C1-C4卤代烷氧基。
为了更高活性和/或易于合成,优选的化合物是:
优选1:上述式I化合物、其N-氧化物和其盐,其中,J是J-1、J-2、J-3或J-6。
优选2:优选的1化合物,其中,
A是O;
R1是H;
1-3个R2基团除H外,且独立地选自:C1-C6烷基、C1-C6卤代烷基、C2-C4氰基烷基、卤素、CN、NO2、哌啶、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚硫酰基和C1-C4卤代烷基磺酰基;和
上述定义的至少1个R2位于NR1C(=A)J部分的邻位。优选3:优选的2化合物,其中,2个R2位于NR1C(=A)J部分的邻位。
优选4:优选的2化合物,其中,
R6是H、C1-C4烷基、C1-C4卤代烷基、卤素或CN;和
R7是H、CH3、CF3、CH2CF3、CHF2、OCH2CF3、OCHF2或卤素。优选5:优选的4化合物,其中,
J是J-1;
R6是Cl或Br;和
R7是卤素、OCH2CF3、OCHF2或CF3。
优选6:优选的4化合物,其中,
J是J-2;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
优选7:优选的4化合物,其中,
J是J-3;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
优选8:优选的4化合物,其中,
J是J-5;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
优选9:优选的4化合物,其中,
J是J-6;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
本发明还涉及含有至少一种式I化合物、其N-氧化物或其盐和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其它组分的组合物。本发明还涉及含有至少一种式I化合物、其N-氧化物或其盐和至少一种其它生物活性化合物或试剂的组合物。本发明优选的组合物是含有上述优选化合物的组合物。
本发明还涉及防治至少一种无脊椎动物害虫的方法,包括将所述无脊椎动物害虫或其环境与至少一种生物有效量式I化合物、其N-氧化物或其盐(例如,以本发明描述的组合物的形式)接触。本发明还涉及这样一种方法,其中,将无脊椎动物害虫或其环境与至少一种生物有效量式I化合物、其N-氧化物或其盐接触,或与生物有效量组合物接触,所述组合物含有至少一种式I化合物、其N-氧化物或其盐和至少一种用于防治无脊椎动物害虫的其它生物有效量生物活性化合物或试剂。优选的使用方法是涉及上述优选化合物和组合物的方法。
通过反应图解1-10中描述的一种或多种下述方法和变更方法,可制得式I化合物。除非另有说明,下述式I和2-32化合物中A、B、J、R1、R2、R6、R7和R8的定义同上文发明概述中的定义。式Ia-c化合物是式I化合物的子集。
反应图解1描述了一种典型的制备方法,包括:在碱存在下,使式2的苯胺或氨基吡啶与式3的酰基氯偶合,得到式Ia化合物。典型的碱包括诸如三乙胺、二异丙基乙胺和吡啶的胺;其它的碱包括诸如氢氧化钠和氢氧化钾的氢氧化物和诸如碳酸钠和碳酸钾的碳酸盐。在某些情况下,使用聚合物负载的酸清除剂是有效的,如与聚合物结合的等当量二异丙基乙胺和二甲基氨基吡啶(例如,PS-CH2N(iPr)2,其中PS是聚苯乙烯主链)。在随后的步骤中,使用各种标准硫转移剂,包括五硫化磷和Lawesson试剂(即,2,4-双(4-甲氧苯基)-1,3-二硫-2,4-二磷杂环丁烷-2,4-二硫化物),可以将式Ia酰胺转化为式Ib硫代酰胺。
反应图解1
如反应图解2所示,另一种制备式Ia化合物的方法包括:在诸如二环己基碳二亚胺(DCC)的脱水剂存在下,使式2的苯胺或氨基吡啶与式4的酸偶合。此处同样可使用聚合物负载的试剂,例如,与聚合物结合的等当量二环己基碳二亚胺(PS-CH2N=C=N-环己基)。由于有关这类反应的合成文献很多,因此,反应图解1和2所示的合成过程仅仅是式I化合物制备方法的代表性实例。
反应图解2
本领域技术人员还认识到,通过很多已知方法,例如但不限于,酸与诸如草酰氯和亚硫酰氯的氯化剂反应,可以由式4所示的酸制得式3所示的酰基氯。式2所示的苯胺或氨基吡啶可以从市场购得或可通过很多已知方法容易地制得。
杂环酸4,其中J为任选被取代的吡唑或任选被取代的吡咯,包括式J-1到J-6的杂环酸。更优选的类似物包括被R5取代的吡唑酸和吡咯酸,其中R5是任选被取代的苯基或吡啶基。在反应图解3-9中详细描述了各自的代表性实例的合成过程。
反应图解3描述了与式J-1有关的式5代表性吡唑羧酸的合成方法,其中R5是2-吡啶基并与氮连接。将吡唑6与式7所示的2,3-二卤吡啶反应,以高收率和高目标区域化学专一性得到1-吡啶基吡唑8。用二异丙基氨基化锂(LDA)使式8化合物金属化,然后用二氧化碳淬灭锂盐,得到式5所示的吡唑羧酸。在实施例1和2中也描述了有关这些过程的其它细节。
反应图解3
其中R7是CF3、Cl或Br的原料吡唑6是已知化合物。其中R7是CF3的吡唑6可以用文献方法制得(J.Fluorine Chem.1991,53(1),61-70)。其中R7是Cl或Br的吡唑也可以用文献方法制得(H.Reimlinger and A.Van Overstraeten,Chem.Ber.1966,99(10),3350-7)。反应图解4描述了R7是Cl或Br的吡唑6的另一种有效制备方法。
反应图解4
用正丁基锂将氨磺酰吡唑9金属化,然后用六氯乙烷(用于R7是Cl)或1,2-二溴四氯乙烷(用于R7是Br)将阴离子直接卤化,得到卤代衍生物10。在室温下用三氟乙酸(TFA)彻底除去氨磺酰基,以高收率得到R7分别是Cl或Br的吡唑6。实施例2中描述了该方法的其它实验细节。
反应图解5描述了与式J-2有关的式14代表性吡唑羧酸的合成方法,其中R5是2-吡啶基并与吡唑环的5位相连。使式12的二甲基氨基亚甲基酮酸酯与取代的肼反应,得到吡啶基吡唑13。优选的R8取代基包括烷基和卤代烷基,特别优选为三氟乙基。通过标准水解法,将酯13转化为式14所示的酸。
反应图解5
反应图解6描述了与式J-3有关的式17代表性吡唑羧酸(其中R5是2-吡啶基并与吡唑环的3位相连)的合成方法以及式14化合物的另一种合成方法。使式12所示的二甲基氨基亚甲基酮酸酯与肼反应,得到吡唑15。将吡唑15与烷基化剂R8-LG(其中LG离去基团,如卤素(如,Br、I)、OS(O)2CH3(甲磺酸根)、OS(O)2CF3、OS(O)2Ph-p-CH3(对甲苯磺酸根)等)反应,得到吡啶基吡唑13和16的混合物。用色谱法可容易地分开该吡唑异构体混合物,并转化成相应的酸。优选的R8取代基包括烷基和卤代烷基。
反应图解6
反应图解7描述了与式J-4有关的式22代表性吡咯羧酸的合成方法,其中R5是2-吡啶基并与吡咯环的氮相连。3-氯-2-氨基吡啶19是已知化合物(参见J.Heterocycl.Chem.1987,24(5),1313-16)。由2-氨基吡啶18制备19的合适的方法包括保护、邻位金属化、氯化以及随后脱保护。用2,5-二甲氧基四氢呋喃处理式19化合物,得到吡咯20。可以使用标准Vilsmeier-Haack甲酰化条件,使吡咯20甲酰化,得到式21的醛。用N-卤丁二酰亚胺(NXS)卤化式21化合物的反应优先发生在吡咯环的4位。使卤代醛氧化得到式22的吡啶基吡咯羧酸。该氧化反应可以在各种标准氧化反应条件下进行。
反应图解7
反应图解8描述了与式J-5有关的式28吡咯羧酸的合成方法,其中R5是苯基或2-吡啶基并与吡咯环的2位相连。使式25的丙二烯与式24的芳基磺酰胺进行环加成(参见Pavri,N.P.;Trudell,M.L.J.Org.Chem.1997,62,2649-2651),得到式26所示的吡咯啉。用氟化四丁基铵(TBAF)处理式26吡咯啉,得到式27的吡咯。将吡咯27与烷基化剂R8-LG(其中LG是上文定义的离去基团)反应,然后水解得到式28的吡咯羧酸。
反应图解8
反应图解9描述了与式J-6有关的式32吡咯羧酸的合成方法,其中R5是2-氯苯基或2-吡啶基。将式29的肉桂酯与甲苯磺酰基甲基胩30(TosMIC)反应,得到式31的吡咯。有关该方法的主要参考资料参见Xu,Z et al J.Org.Chem.1998,63,5031-5041。使式31化合物与烷基化剂R8-LG(其中LG是上文定义的离去基团)反应,然后水解得到式32的吡咯羧酸。
反应图解9
反应图解10描述了式Ic吡唑酰胺类似物的合成方法。该方法利用了式8所示的锂化衍生物。用二异丙基氨基化锂(LDA)处理式8化合物,然后用异氰酸芳基酯淬灭锂盐,得到式Ic化合物,其为式I化合物的子集。实施例1描述了该方法的其它细节。
反应图解10
应当认识到,上述用于制备式I化合物的某些试剂和反应条件可能与中间体中存在的某些官能团不相容。在这些情况下,在合成中加入保护/脱保护步骤或官能团互变,将有助于得到目标产物。保护基团的使用和选择对于化学合成技术人员而言是显而易见的(例如,参见Greene,T.W.;Wuts,P.G.M.Protective Groups in OrganicSynthesis,2nd ed.;Wiley:New York,1991)。本领域技术人员能够认识到,在某些情况下,在按照任一单独的反应图解所述引入特定的试剂后,可能需要进行未详细说明的其它常规合成步骤,以便完成式I化合物的合成。本领域技术人员还会认识到,可能需要按一定的次序进行上述反应图解中的多个步骤,且该次序不同于所提出的制备式I化合物的特定工序所暗示的次序。
本领域技术人员还会认识到,本发明中描述的式I化合物和中间体可以进行各种素电反应、亲核反应、自由基反应、有机金属反应、氧化反应和还原反应,以加上取代基或修饰存在的取代基。
无需进一步的详细描述,相信根据上文描述,本领域技术人员能够在最大可能的范围内利用本发明。因此,下述实施例仅用于说明本发明,而不以任何方式限制本发明。除了色谱溶剂混合物以外,或者除非另有说明,百分比是指重量百分比。除非另有说明,色谱溶剂混合物的份和百分比是指体积份和体积百分比。1H NMR光谱以离开四甲基硅烷峰的低场距离ppm记录;s是单峰,d是双峰,t是三重峰,q是四重峰,m是多重峰,dd是双二重峰,dt是双三重峰和brs是宽单峰。
实施例1
N-(2-氯-6-甲基苯基)-1-(3-氯-2-吡啶基)-3-(三氟甲基)
-1H-吡唑-5-甲酰胺的制备
步骤A:3-氯-2-[3-(三氟甲基)-1H-吡唑-1-基]吡啶的制备
将碳酸钾(166.0g,1.2mol)加入2,3-二氯吡啶(99.0g,0.67mol)和3-(三氟甲基)-吡唑(83g,0.61mol)在无水N,N-二甲基甲酰胺(300mL)中的混合物中,然后将反应加热至110-125℃反应48小时。冷却反应至100℃,经Celite硅藻土助滤剂过滤以除去固体。通过常压蒸馏除去N,N-二甲基甲酰胺和过量的二氯吡啶。减压蒸馏产物(b.p.139-141℃,7mm),得到透明黄色油状标题化合物(113.4g)。
1H NMR(CDCl3)δ6.78(s,1H),7.36(t,1H),7.93(d,1H),8.15(s,1H),8.45(d,1H)。
步骤B:1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-甲酸的制备
经套管向3-氯-2-[3-(三氟甲基)-1H-吡唑-1-基]吡啶(即,步骤A的吡唑产物)(105.0g,425mmol)的-75℃无水四氢呋喃(700mL)溶液中加入二异丙基氨基化锂(425mmol)的-30℃无水四氢呋喃(300mL)溶液。搅拌该深红色溶液15分钟,然后在-63℃下鼓泡通过二氧化碳直至溶液变成浅黄色并停止放热。再搅拌反应20分钟,然后用水(20mL)淬灭。减压除去溶剂,并在乙醚和0.5N氢氧化钠水溶液之间分配反应混合物。用乙醚(3x)洗涤水提物,并用Celite硅藻土助滤剂过滤以除去残余固体,然后酸化至pH约为4,此时形成橙色油状物。剧烈搅拌水性混合物,再加入酸使pH降至2.5-3。橙色油状物凝固成颗粒状固体,过滤并依次用水和1N盐酸洗涤,在50℃下真空干燥,得到黄白色固体标题产物(130g)。(根据类似的操作步骤,由另一种线路得到的产物在175-176℃熔化。)
1H NMR(DMSO-d6)δ7.61(s,1H),7.76(dd,1H),8.31(d,1H),8.60(d,1H)。
步骤C:N-(2-氯-6-甲基苯基)-1-(3-氯-2-吡啶基)-3-(三氟甲基)-
1H-吡唑-5-甲酰胺的制备
将3-氯-2-[3-(三氟甲基)-1H-吡唑-1-基]吡啶(即,步骤A的吡唑产物)(2.72g,11.14mmol)的四氢呋喃(50ml)溶液冷却至-70℃。用2分钟加入二异丙基氨基化锂(2M THF/庚烷溶液,5.5mL,11.0mmol),并搅拌混合物15分钟。用注射器加入异氰酸2-氯-6-甲基苯酯(1.90g,11.33mmol)。使混合物升至20℃,并用饱和氯化铵水溶液(50mL)淬灭。用乙酸乙酯(100mL)萃取反应物,用硫酸镁干燥并浓缩。经硅胶色谱法(用3∶1己烷/乙酸乙酯-1∶1己烷/乙酸乙酯进行梯度洗脱)得到本发明的固体标题化合物(3.0g),熔点212-213℃。
1H NMR(CDCl3)δ2.24(3H),7.1(1H),7.2(1H),7.25(1H),7.4(1H),7.6(1H),7.9(1H),8.5(1H)。
实施例2
N-(2-溴-4,6-二氟苯基)-1-(3-氯-2-吡啶基)-3-溴
-1H-吡唑-5-甲酰胺的制备
步骤A:3-溴-N,N-二甲基-1H-吡唑-1-磺酰胺的制备
向N-二甲基氨磺酰吡唑(44.0g,0.251mol)的-78℃无水四氢呋喃(500mL)溶液中滴加正丁基锂溶液(2.5M己烷溶液,105.5mL,0.264mol),同时保持温度低于-60℃。在滴加过程中形成了不透明固体。一旦滴加完毕,将反应混合物再保持15分钟,然后,滴加1,2-二溴-四氯乙烷(90g,0.276mol)的四氢呋喃(150mL)溶液,同时保持温度低于-70℃。反应混合物变为透明橙色;再持续搅拌15分钟。移去-78℃冷却浴,用水(600mL)淬灭反应。用二氯甲烷(4x)萃取反应混合物,用硫酸镁干燥有机萃取液并浓缩。用硅胶色谱法进一步提纯粗产物(用二氯甲烷-己烷(50∶50)作为洗脱液),得到透明无色油状标题产物(57.04g)。
1H NMR(CDCl3)δ3.07(d,6H),6.44(m,1H),7.62(m,1H)。
步骤B:3-溴吡唑的制备
向三氟乙酸(70mL)中缓慢加入3-溴-N,N-二甲基-1H-吡唑-1-磺酰胺(即,步骤A的溴代吡唑产物)(57.04g)。室温搅拌反应混合物30分钟,然后减压浓缩。将残余物溶解在己烷中,滤除不溶固体,蒸发己烷得到油状粗产物。用硅胶色谱法进一步提纯粗产物(用乙酸乙酯/二氯甲烷(10∶90)作为洗脱液),得到油状物。将油状物吸收在二氯甲烷中,用碳酸氢钠水溶液中和,用二氯甲烷(3x)萃取,用硫酸镁干燥并浓缩,得到白色固体标题产物(25.9g),熔点:61-64℃。
1H NMR(CDCl3)δ6.37(d,1H),7.59(d,1H),12.4(br s,1H)。
步骤C:2-(3-溴-1H-吡唑-1-基)-3-氯吡啶的制备
向2,3-二氯吡啶(27.4g,185mmol)和3-溴吡唑(即,步骤B的产物)(25.4g,176mmol)在N,N-二甲基甲酰胺(88mL)中的混合物中加入碳酸钾(48.6g,352mmol),并将反应混合物加热至125℃反应18小时。冷却反应混合物至室温,将其倾入冰水(800mL)中。形成沉淀。将沉淀出的固体搅拌1.5小时,过滤并用水(2×100mL)洗涤。将固体滤饼溶解在二氯甲烷中,依次用水、1N盐酸、饱和碳酸氢钠水溶液和盐水洗涤。然后用硫酸镁干燥有机萃取液并浓缩得到39.9g粉红色固体。将固体粗产物悬浮在己烷中并剧烈搅拌1小时。滤出固体,用己烷洗涤并干燥,得到黄白色粉末标题产物(30.4g),用NMR测定其纯度>94%。该原料无需提纯直接用于步骤D中。
1H NMR(CDCl3)δ6.52(s,1H),7.30(dd,1H),7.92(d,1H),8.05(s,1H),8.43(d,1H)。
步骤D:3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸的制备
以保持温度低于-71℃的速率,向2-(3-溴-1H-吡唑-1-基)-3-氯吡啶(即,步骤C的产物)(30.4g,118mmol)的-76℃无水四氢呋喃溶液(250mL)中滴加二异丙基氨基化锂(118mmol)的四氢呋喃溶液。在-76℃下搅拌反应混合物15分钟,然后鼓泡通过二氧化碳10分钟,使温度升至-57℃。将反应混合物升至-20℃,并用水淬灭。浓缩反应混合物,然后吸收在水(1L)和乙醚(500mL)中,加入氢氧化钠水溶液(1N,20mL)。用乙醚洗涤水提物并用盐酸酸化。滤出沉淀的固体,用水洗涤并干燥,得到黄褐色固体标题产物(27.7g)。(根据类似的操作步骤,由另一种线路得到的产物在200-201℃熔化。)
1H NMR(DMSO-d6)δ7.25(s,1H),7.68(dd,1H),8.24(d,1H),8.56(d,1H)。
步骤E:N-(2-溴-4,6-二氟苯基-1-(3-氯-2-吡啶基)-3-溴-1H-吡唑
-5-甲酰胺的制备
在室温下,将草酰氯(0.043mL,0.5mmol)加入到3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酸(即,步骤D的产物)(200mg,0.66mmol)和两滴N,N-二甲基甲酰胺(DMF)在30mL二氯甲烷中的混合物中,并搅拌反应10分钟。然后,加入催化量的4-(二甲基氨基)吡啶,然后滴加三乙胺(184mL,1.4mmol)和2-溴-4,6-二氟苯胺在10mL二氯甲烷中的混合物。搅拌反应过夜,然后浓缩近干。用硅胶色谱法(用9∶1-1∶1己烷/乙酸乙酯进行梯度洗脱)得到油状物。然后在干冰中冷却该油状物,并用乙醚/己烷研磨,得到作为本发明化合物的固体标题化合物(0.22g),熔点138-139℃。
1H NMR(CDCl3)δ6.90(m,1H),6.98(s,1H),7.18(m,1H),7.40(dd,1H),7.55(br s,1H),7.90(d,1H),8.47(d,1H)。
实施例3
1-(3-氯-2-吡啶基)-N-(2,4-二氯苯基)-3-(三氟甲基)
-1H吡唑-5-甲酰胺的制备
向1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-甲酸(即,实施例1步骤B的产物)(6.0g,20.76mmol)的二氯甲烷(60mL)溶液中加入草酰氯(5.7g,44.88mmol),然后加入两滴DMF。搅拌混合物2小时,然后在旋转蒸发器上减压浓缩混合物,将其吸收至氯仿中,二次浓缩除去残余的草酰氯。得到的酰基氯直接用于下一步反应。
向2,4-氯苯胺(382mg,2.35mmol)的无水四氢呋喃(3mL)溶液中加入酰基氯(307mg,1.0mmol)的氯仿(3mL)溶液,并在室温搅拌混合物4小时,然后在氯仿和饱和碳酸氢钠水溶液之间分配反应。用硫酸镁干燥氯仿萃取液,过滤并减压浓缩。用8∶1己烷/乙酸乙酯作为洗脱液,经硅胶色谱法得到67mg作为本发明化合物的无色油状标题产物。
1H NMR(CDCl3)δ7.16(s,1H),7.2(m,1H),7.42(s,1H),7.48(dd,1H),7.94(dd,1H),8.17(dd,1H),8.38(br s,1H),8.52(dd,1H)。
实施例4
索引表B的酰胺化合物库的制备
向1-(3-氯-2-吡啶基)-3-(三氟甲基)-1H-吡唑-5-甲酸(即,实施例1步骤B的产物)(1.467g,6.3mmol)的二氯甲烷(25mL)溶液中加入草酰氯(2.6mL,37.8mmol)。在停止释放最初气体后,加热回流溶液2.5小时。冷却混合物至室温并浓缩。用二氯甲烷(3×25mL)研磨得到的黄色油状残余物,以除去微量草酰氯。用二氯甲烷稀释残余物至63mL,制得该酰基氯的0.1M储备液。该储备液直接用于下一步反应。制备用于该化合物库的各种苯胺的0.1M二氯甲烷储备液。制备含有0.5mg/mL 4-(二甲氨基)吡啶的0.83M三乙胺的二氯甲烷储备液。在干燥箱中,用移液管将苯胺储备液(250μL)分布到96孔板的各孔中。向各孔中加入酰基氯储备液(300μL),然后加入三乙胺储备液(50μL)。将孔板密封,从干燥箱中移出,并置于被修饰的Flexchem烘箱(Robbins Scientific Co.Sunnyvale,California,USA)中,在氮气气氛下室温搅拌过夜。然后,移去孔板盖,并向每个孔中加入三甲醇氨基甲烷树脂(75mg)。再密封孔板并搅动过夜。将孔板内容物滤至96孔微量滴定板中,并用200μL二氯甲烷洗涤。将合并的滤液加入到预先准备的Whatman MBPP滤板(预先向各孔中加入200mgHydromatrix(外加煅烧硅藻土)(Varian,Inc.Walnut Creek,California,USA),然后用200μL 0.1M氢氧化钠水合)中。使板自流过滤到预称皮重的小平板(micronics plate)中,并用300μL二氯甲烷将Hydromatrix洗涤至同一板中。取样进行LCMS(液质联用色谱)分析,然后减压除去溶剂。制得的库见索引表B。使用LCMS,在微量LCTTM TOF(飞行时间)质谱仪(Macromass Inc.Manchester,UK)上,以电喷雾电离模式操作,收集100-1200道尔顿数据9分钟,对产物进行分析。LC系统是带有2.1×30mm Zorbax SB-C18快速拆分柱的WatersAlliance 2790(Waters Co.Milord,Massachusetts,USA)。6分钟线性梯度采用含有0.1%甲酸的10%乙腈水溶液-含有0.1%甲酸的100%乙腈,并保持3分钟,以洗脱化合物。每次注射3μL约0.5mg/mL溶液。观测到的M+H(质子化分子离子)见索引表B。
通过本发明描述的方法以及本领域的已知方法,可制得下表1-7中的化合物。表中使用的缩写符号如下:t表示叔、s表示仲、n表示正、i表示异、c表示环、Me表示甲基、Et表示乙基、Pr表示丙基、i-Pr表示异丙基、t-Bu表示叔丁基、Ph表示苯基、OMe表示甲氧基、OEt表示乙氧基、SMe表示甲硫基、SEt表示乙硫基、CN表示氰基、NO2表示硝基、TMS表示三甲基甲硅烷基、S(O)Me表示甲基亚硫酰基和S(O)2Me表示甲磺酰基。
表1
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl | HHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClCl | H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl | HHHHHHHHHHHHHHHHHH | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClCF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHHHHHHHHHHHHHHHH | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrOCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CN | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CN | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | HHHHHHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | HHHHHHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br | 6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br | 6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3CF3 | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
表2
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
H2-F2-Cl | HHH | HHH | MeMeMe | H2-F2-Cl | HHH | HHH | OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | HHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Bt2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | HHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I | H4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I | H4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrH | 6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeCHF2 | 2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-CF3 | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrH | 6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I | H4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
表3
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | HHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | HHHHHHHHHHHHHHHHHHHHHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | HHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | HHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeCHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF3 | 4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHHHHHHHHHHH | 6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
表4
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | HHHHHHHH | HHHHHHHH | ClClClClClClClCl | H2-F2-Cl2-Br2-I2-Me2-Et2-CF3 | HHHHHHHH | HHHHHHHH | ClClClClClClClCl |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I | H4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I | H4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHHH4-F4-F | HHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHHH4-F4-F | HHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClCl |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHH | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBr | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHH | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHH | ClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClClBrBr |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | 2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | 4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | 2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | 4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | HHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | 2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | HHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2C | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F | BrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBrBr |
R7连接至位置5 | R7连接至位置4 | ||||||
R 2a | R 2b | R 2c | R 7 | R 2a | R 2b | R 2c | R 7 |
2-Et2-CF32-OCF2H | 4-Br4-Br4-Br | 6-F6-F6-F | BrBrBr | 2-Et2-CF32-OCF2H | 4-Br4-Br4-Br | 6-F6-F6-F | BrBrBr |
表5
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl | HHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I | HHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl | HHHHHHHHHHHHHHHHHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I | 4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I | 4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | HHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-O2-Me2-Et2-CF32-OCF2H2-F | HHHHHHHHHHHHHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHHHHHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeCHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHH4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F | 6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHH | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH6-Cl6-Cl6-Cl | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br | 6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | HHHHHHHHHHHHHHHHHHH | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
表6
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
H2-F2-Cl2-Br2-I | HHHHH | HHHHH | MeMeMeMeMe | H2-F2-Cl2-Br2-I | HHHHH | HHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl | HHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl | HHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF34-CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | 4-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHHH4-F | HHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F | 4-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHHHH4-F | HHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMe | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHHH | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-FHHH | MeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeMeCHF2CHF2CHF2 | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-CF32-OCF2H2-F | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-BrHH4-F | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-F6-F6-Cl | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-F | HHHHH4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-I4-I4-I4-I4-I4-I4-I4-CF3 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-MO2-Et | 4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-F4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl | 6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
R 2a | R 2b | R 2c | R 8 | R 2a | R 2b | R 2c | R 8 |
2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et | 4-CF34-CF34-CF34-CF34-CF34-CF34-CN4-CN4-CN4-CN4-CN4-CN4-CNHHHHHHHHHHHHHHHHHHHHHH | HHHHHHHHHHHHH6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 | 2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H2-F2-Cl2-Br2-I2-Me2-Et2-CF32-OCF2H | 4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Cl4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br4-Br | 6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Cl6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-Br6-F6-F6-F6-F6-F6-F6-F6-F | CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2CHF2 |
表7
U | V | W | R 2a | R 2b | R 7 |
NNNNNNNNNNNNNNNNNNNNNNNNNN | CHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCHCH | CHCHCHCHCHCHC-ClC-CF3CHCHCHCHCHCHC-ClC-CF3CHCHCHCHCHCHC-ClC-CF3CHCH | HFClBrMeCF3ClClHFClBrMeCF3ClClHFClBrMeCF3ClClHF | HHHHHHHHHHHHHHHHHHHHHHHHHH | ClClClClClClClClBrBrBrBrBrBrBrBrCF3CF3CF3CF3CF3CF3CF3CF3OCH2CF3OCH2CF3 |
U | V | W | R 2a | R 2b | R 7 |
NNNNNNC-ClC-ClC-MeCHCHC-ClC-ClC-MeCHCHC-ClC-ClC-MeCHCHC-ClC-ClC-MeCHCHC-ClC-ClC-MeCHCHC-FCHC-ClC-ClC-MeCH | CHCHCHCHCHCHNNNNNNNNNNNNNNNNNNNNCHCHCHC-ClC-CF3C-FCHCHCHCHC-Cl | CHCHCHCHC-ClC-CF3CHC-ClCHCHCHCHC-ClCHCHCHCHC-ClCHCHCHCHC-ClCHCHCHNNNNNNNNNNN | ClBrMeCF3ClClHHHMeClHHHMeClHHHMeClHHHMeClHClHClCF3FHHClHCl | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHFHHHHH | OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClBrBrBrBrBrCF3CF3CF3CF3Cf3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3ClClClClClClClBrBrBrBr |
U | V | W | R 2a | R 2b | R 7 |
CHC-FCHC-ClC-ClC-MeCHCHC-FCHC-ClC-ClC-MeCHCHC-FCH | C-CF3C-FCHCHCHCHC-ClC-CF3C-FCHCHCHCHC-ClC-CF3C-FCH | NNNNNNNNNNNNNNNNN | CF3FHHClHClCF3FHHClHClCF3FH | HFHHHHHHFHHHHHHFH | BrBrBrCF3CF3CF3CF3CF3CF3CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3OCH2CF3 |
制剂/用途
本发明化合物一般是以含有适宜农用的载体的制剂或组合物的形式使用,所述载体含有至少一种液体稀释剂、固体稀释剂或表面活性剂。对制剂或组合物组分进行选择,使其与活性组分的物理性质、施用方式及诸如土壤类型、湿度和温度的环境因素相适应。有效的制剂包括液体,如溶液(包括乳油)、悬浮液、乳液(包括微乳液和/或悬浮液)等,所述液体可任选被增稠成凝胶。有效的制剂还包括固体,如粉剂、散剂、粒剂、丸剂、片剂、薄膜等,所述固体可以是水分散性的(“可湿性”)或是水溶性的。活性组分可以被(微)胶囊包封并进一步形成悬浮液或固体制剂;或者可以将整个活性组分制剂包封(或“包衣”)。胶囊包封可以防治或迟延释放活性组分。可喷雾制剂可以被扩散在合适的介质中,并以每公顷约1-数百升的喷雾体积使用。高浓度组合物主要是作为中间体用于进一步配制。
制剂一般含有有效量活性组分、稀释剂和表面活性剂,其含量范围大致如下,其总和为100重量%。
重量百分数 | |||
活性组分 | 稀释剂 | 表面活性剂 | |
水分散性和水溶性粒剂、片剂和散剂悬浮液、乳剂、溶液(包括乳油)粉剂粒剂和丸剂高浓度组合物 | 5-905-501-250.01-9990-99 | 0-9440-9570-995-99.990-10 | 1-150-150-50-150-2 |
在Watkins et al.,Handbook of Insecticide Dust Diluentsand Carriers,2nd Ed.,Dorland Books,Caldwell,New Jersey中描述了典型固体稀释剂。在Marsden,Solvents Guide,2nd Ed.,Interscience,New York,1950.中描述了典型液体稀释剂。在McCutcheon′s Detergents and Emulsifiers Annual,Allured Publ.Corp.,Ridgewood,New Jersey以及Sisely and Wood,Encyclopedia of Surface Active Agents,Chemical Publ.Co.,Inc.,New York,1964中列举了表面活性剂和推荐的用途。所有制剂均可含有少量添加剂以减少泡沫、结块、腐蚀和微生物生长等或可含有少量增稠剂以增加粘度。
表面活性剂包括,例如,聚乙氧基化醇、聚乙氧基化烷基酚、聚乙氧基化脱水山梨醇脂肪酸酯、磺基琥珀酸二烷基酯、硫酸烷基酯、烷基苯磺酸盐、有机硅化合物、N,N-二烷基牛磺酸盐、木素磺酸盐、萘磺酸盐甲醛缩合物、多羧酸盐和聚氧乙烯/聚氧丙烯嵌段共聚物。固体稀释剂包括,例如,粘土(如,膨润土、蒙脱石、硅镁土和高岭土)、淀粉、糖、二氧化硅、滑石、硅藻土、尿素、碳酸钙、碳酸钠、碳酸氢钠以及硫酸钠。液体稀释剂包括,例如,水、N,N-二甲基甲酰胺、二甲亚砜、N-烷基吡咯烷酮、乙二醇、聚丙二醇、石蜡、烷基苯、烷基萘、橄榄油、蓖麻油、亚麻子油、桐油、芝麻油、玉米油、花生油、棉籽油、豆油、菜籽油、椰子油、脂肪酸酯、酮(如,环己酮、2-庚酮、异佛尔酮和4-羟基-4-甲基-2-戊酮)和醇(如,甲醇、环己醇、癸醇和四氢糠醇)。
通过简单地混合各组分可以制得溶液(包括乳油)。通过掺混并通常在例如锤磨机或流能磨中进行研磨可以制得粉剂和散剂。悬浮液一般通过湿磨法制备,参见,例如,US 3,060,084。通过将活性物质喷雾到预先形成的颗粒载体上或者通过附聚技术可制得粒剂和丸剂。参见Browning,“Agglomeration”,Chemical Engineering,December 4,1967,pp 147-48;Penny′s Chemical Engineer′sHandbook,4th Ed.,McGraw-Hill,New York,1963,pp 8-57及其下文和WO 91/13546。丸剂可以如US 4,172,714中描述的方法制得。水分散性和水溶性粒剂可以如同US 4,144,050、US 3,920,442和DE3,246,493中教导的方法制得。片剂可以按US 5,180,587、US5,232,701和US 5,208,030的教导制备。薄膜可以如GB 2,095,558和US 3,299,566中的教导制备。
关于制剂工艺的其它资料可以参见T.S.Woods,“TheFormulator′s Toolbox-Product Forms for Modern Agricul ture”inPesticide Chemistry and Bioscience;The Food-EnvironmentChallenge,T.Brooks and T.R.Roberts,Eds.,Proceedings ofthe 9th International Congress on Pesticide Chemistry;TheRoyal Society of Chemistry,Cambridge,1999,pp.120-133。还可以参见US 3,235,361第6栏第16行-第7栏第19行和实施例10-41;US 3,309,192第5栏第43行-第7栏第62行和实施例8、12、15、39、41、52、53、58、132、138-140、162-164、166、167和169-182;US 2,891,855第3栏第66行-第5栏第17行和实施例1-4;Klingman,Weed Control as a Science,John Wiley and Sons,Inc.,New York,1961,pp 81-96;和Hance et al.,Weed ControlHand book,8th Ed.,Blackwell Scientific Publications,Oxford,1989。
在下述实施例中,所有百分数是重量百分数,所有制剂都用常规方法制得。化合物编号是指索引表A中的化合物。
实施例A
可湿性粉剂
化合物1 65.0%
十二烷基苯酚聚乙二醇醚 2.0%
木素磺酸钠 4.0%
硅铝酸钠 6.0%
蒙脱石(煅烧的) 23.0%
实施例B
粒剂
化合物1 10.0%
硅镁土颗粒(低挥发性物质,
0.71/0.30mm;美式筛25-50目) 90.0%
实施例C
挤压丸剂
化合物1 25.0%
无水硫酸钠 10.0%
粗木素磺酸钙 5.0%
烷基萘磺酸钠 1.0%
钙/镁膨润土 59.0%
实施例D
乳油
化合物1 20.0%
油溶性磺酸盐和聚氧乙烯醚的掺混物 10.0%
异佛尔酮 70.0%
实施例E
粒剂
化合物1 0.5%
纤维素 2.5%
乳糖 4.0%
玉米粉 93.0%
本发明化合物的特征在于其良好的代谢和/或土壤残留特性,并具有防治各种各样农艺和非农艺无脊椎动物害虫的活性。(在本发明中,“无脊椎动物害虫防治”是指抑制无脊椎动物害虫发育(包括致死),使其进食明显减少,或是指抑制由害虫造成的其它损伤或损害;有关术语类似进行了定义。)正如本发明所提及的那样,术语“无脊椎动物害虫”包括具有经济意义的节肢动物害虫、腹足类动物害虫和线虫害虫。术语“节肢动物”包括昆虫、螨、蜘蛛、蝎、蜈蚣、千足虫、pillbugs和symphylans。术语“腹足类动物”包括蜗牛、蛞蝓和其它柄眼目。术语“线虫”包括所有的寄生虫,例如,蛔虫、犬恶丝虫和植食性线虫(线虫纲)、吸虫(Tematoda)、棘头纲和绦虫(多节绦虫亚纲)。本领域技术人员应当知道,并非所有的化合物对所有害虫都具有同等效力。本发明化合物对具有经济意义的农艺和非农艺害虫具有活性。术语“农艺”是指诸如用于食物和纤维的农作物的生产,包括谷类作物(例如,小麦、燕麦、大麦、黑麦、稻、玉米)、大豆、蔬菜作物(例如,莴苣、卷心菜、西红柿、豆)、马铃薯、甜薯、葡萄、棉和树生水果(例如,梨果、核果和柑橘属果)的生长。术语“非农艺”是指其它园艺作物(例如,非生长于田野的林区作物、温室作物、苗圃或观赏植物)、公众(人类)和动物动物健康、家庭和商业建筑物、家庭用品和储存产品用品或害虫。为了无脊椎动物害虫的防治范围和经济上的意义,本发明的优选实施方案是:通过防治无脊椎动物害虫,保护农艺作物棉花、玉米、大豆、稻、蔬菜作物、马铃薯、甜薯、葡萄和树生果实(免遭由无脊椎动物害虫造成的损失或损害)。农艺和非农艺害虫包括鳞翅目幼虫,例如,夜蛾科中的粘虫、切根虫、夜蛾(loopers)和heliothines(例如,草地粘虫(草地粘虫J.E.Smith)、甜菜粘虫(甜菜夜蛾Huber)、小地虎(小地蝉Hufnagel)、粉纹夜蛾(粉纹夜蛾Huber)、烟夜蛾(烟夜蛾Fabricius));螟蛾科的钻蛀虫、鞘蛾、美国白蛾、coneworms、cabbageworms和雕叶虫(例如,欧洲玉米螟(玉米螟Huber)、脐橙螟(Ainyelois transitella Walker)、玉米根网螟(玉米根草螟Clemens)、草皮网螟(Herpetogramma licarsisalisWalker));卷叶蛾科中的卷叶蛾、芽虫、籽虫和果虫(例如,苹果蠹蛾(苹蠹蛾Linnaeus)、葡萄小卷蛾(Endopizaviteana Clemens)、梨小食心虫(梨小食心虫Busck));以及许多其它具有经济意义的鳞翅目(例如,小菜蛾(小菜蛾Linnaeus)、红铃虫(红铃虫Saunders)、卷叶蛾(舞毒蛾Linnaeus));蜚蠊总科的稚虫和成虫,包括Blattellidae和蜚蠊科的蟑螂(例如,东方蟑螂(东方蜚蠊Linnaeus)、亚洲蟑螂(亚洲蜚蠊Mizukubo)、德国小蠊(德国小蠊Linnaeus)、褐带蜚蠊(长须蜚蠊Fabricius)、美洲大蠊(美洲大蠊Linnaeus)、褐色大蠊(褐色大蠊Burmeister)、马德拉蜚蠊(马德拉蜚蠊Fabricius));鞘翅目的食叶幼虫和成虫,包括长角象虫科、豆象科和象鼻虫科的象鼻虫(例如,棉鼻虫(棉铃象甲Boheman)、稻象甲(美洲稻象甲Kuschel)、谷象(谷象Linnaeus)、米象(米象Linnaeus));叶甲科中的跳甲、黄守瓜、根虫、金花虫、马铃薯甲虫和潜叶蛾(例如,马铃薯甲虫(马铃薯甲虫Say)、玉米根叶甲(玉米幼芽根叶甲LeConte));Scaribaeidae科的金龟子和其它甲虫(例如,日本弧丽金龟(日本丽金龟Newman)和欧洲金龟(Rhizotrogus majalis Razoumowsky));皮蠹科的红缘皮蠹;叩头虫科的捻转血矛线虫;棘胫小蠹科的小蠹虫和拟步行虫科的谷盗。另外,农艺和非农艺害虫包括:革翅目成虫和幼虫,包括球螋科的蠼螋(例如,大蠼螋(欧洲球螋Linnaeus)、黑蠼螋(Chelisoches morioFabricius));半翅目和同翅目科成虫和稚虫,例如,盲蝽科的盲蝽、蝉科的蝉、大叶蝉科的叶蝉(例如,微叶蝉属)、樗鸡总科和飞虱科的飞虱、角蝉科的角蝉、木虱科的木虱、粉虱科的飞虱、蚜科的蚜虫、根瘤蚜科的根瘤蚜、粉蚧科的粉蚧、来自介壳虫科、盾蚧科和绵蚧科的介壳虫、网蝽科的网蝽、蝽科的蝽象、长蝽科的cinch bugs(例如,长蝽属)和其它实蝽、沫蝉科的沫蝉、缘蝽科的南瓜绿蝽以及红蝽科的红蝽和棉红蝽。还包括蜱螨目(螨类)成虫和稚虫,如叶螨科中的叶螨和茶红叶螨(例如,苹果全爪螨Koch、二点叶螨(二点叶螨Koch)、麦克旦尼氏红叶螨(麦克旦尼氏红叶螨McGregor))、细须螨科科中的短须螨(例如,柑短须螨(柑短须螨McGregor))、瘿螨科中的锈蜘蛛和芽螨(bud mites)和其它食叶螨以及对人类和动物健康重要的螨类,即,表皮螨科中的尘螨、脂螨科的腺囊螨、食甜螨科的谷螨、硬蜱目中的扁虱(例如,鹿蜱(Ixodes scapulars Say)、澳大利亚多毛硬蜱(诺伊曼全环硬蜱)、美国犬蜱(美国犬蜱Say)、美洲花蜱(美洲花蜱Linnaeus)以及痒螨科、蒲螨科和疥螨科中的疥癣和疥螨;直翅目的成虫和幼虫,包括蝗虫、蚱蜢和蟋蟀(例如,迁徙蝗(例如,迁徙蚱蜢Fabricius、M.differentialis Thomas)、美洲蚱蜢(例如,美洲蚱蜢Drury)、沙漠蝗(沙漠蝗Forskal)、迁徙蝗(迁徙蝗Linnaeus)、家蟋蟀(家蟋蟀Linnaeus)、蝼蛄(蝼蛄属));双翅目成虫和幼虫,包括潜叶蛾、摇蚊科、果蝇(实蝇科)、黄潜蝇(例如,瑞典麦杆蝇Linnaeus)、粪蛆、普通家蝇(例如,家蝇Linnaeus)、小家厕蝇(例如,黄腹厕蝇Linnaeus、F.femoralis Stein)、厩蝇(例如,螫蝇属calcitransLinnaeus)、秋家蝇、角蝇、丽蝇(例如,金蝇属、黑丽蝇属)和其它蝇状双翅昆虫害虫、虻科(例如,虻属)、狂蝇科(例如,马蝇属、狂蝇属)、家畜幼虫(例如,皮蝇属)、鹿蝇(例如,斑虻属)、羊蜱蝇(例如,绵羊虱蝇Linnaeus)和其它短角亚目、蚊子(例如,伊蚊属、按蚊属、库蚊属)、墨蚊科(例如,原蚋属、蚋属)、蠓、毛蠓、尖眼蕈蚊和其它长角亚目;缨翅目成虫和幼虫,包括葱蓟马(葱蓟马Lindeman)和其它食叶蓟马属;膜翅目昆虫害虫,包括蚂蚁(例如,红木工蚁(红木工蚁Fabricius)、黑木工蚁(黑木工蚁DeGeer)、法老蚁(法老蚁Linnaeus)、小火蚁(小火蚁Roger)、火蚁(火蚁Fabricius)、红外来火蚁(红外来火蚁Buren)、阿根廷蚁(阿根廷蚁Mayr)、家褐蚁(家褐蚁Latreille)、铺道蚁(铺道蚁Linnaeus)、玉米田蚁(玉米田蚁Forster)、臭家蚁(臭家蚁Say)、蜜蜂(包括木蜂)、大黄蜂、黄蜂、鲜黄色胡蜂和胡蜂;等翅目昆虫害虫,包括黄胸散白蚁(黄胸散白蚁Kollar)、西方犀白蚁(西方犀白蚁Banks)、家白蚁(家白蚁Shiraki)、西印度干木白蚁(干木切白蚁Snyder)和其它具有经济意义的白蚁;弹尾目昆虫害虫,例如,银鱼(西洋表鱼Linnaeus)和家衣鱼(家衣鱼Packard);食毛目昆虫害虫,包括头虱(头虱De Geer)、体虱(体虱Linnaeus)、雏鸡羽虱(雏鸡羽虱Nitszch)、狗羽虱(狗羽虱De Geer)、食毛鸟虱(鸡姬虱De Geer)、羊羽虱(羊羽虱Schrank)、牛盲虱(牛盲虱Nitzsch)、牛颚虱(牛颚虱Linnaeus)和其它攻击人类和动物的吸吮和咀嚼式寄生虱;Siphonoptera目昆虫害虫,包括东方鼠蚤(印鼠客蚤Rothschild)、猫栉头蚤(猫栉头蚤Bouche)、猫栉头蚤(狗栉头蚤Curtis)、禽蚤(禽蚤Schrank)、禽毒蚤(禽毒蚤Westwood)、人蚤(人蚤Linnaeus)和其它折磨哺乳动物和鸟类的蚤。所包括的其它节肢动物害虫包括:蜘蛛目中的蜘蛛,例如,褐皮花蛛(褐皮花蛛Gertsch &Mulaik)和毒冠蛛(毒冠蛛Fabricius),和蚰蜒形目中的蜈蚣,如家蚰蜒(家蚰蜒Linnaeus)。本发明化合物还对线虫纲害虫、多节绦虫亚纲害虫、吸虫纲害虫和棘头纲害虫具有活性,所述害虫包括具有经济意义的圆线虫目、蛔虫目、尖尾目、小杆目、旋尾目和嘴刺目,例如,但不限于,具有经济意义的农业害虫(即,根结线虫属中的根结线虫、草地垫刃线虫属中的损伤线虫、鬃根线虫属中的鬃根线虫等)以及动物和人类健康害虫(即,所有具有经济意义的吸虫、绦虫和蛔虫,例如,马体内的寻常圆线虫、狗体内的犬弓蛔虫、羊体内的捻转血茅线虫、狗体内的犬恶丝虫、马体内的叶形裸头绦虫、反刍动物体内的肝片吸虫Linnaeus等)。
本发明化合物对下述害虫具有特别高的活性:鳞翅目(例如,棉叶波蚊夜蛾Hübner(棉叶波蚊夜蛾)、果树黄卷蛾Walker(果树卷叶蛾)、A.rosana Linnaeus(欧洲卷叶蛾)和其它黄卷蛾属、二化螟Walker(水稻二化螟)、稻纵卷叶螟(稻卷叶蛾)、玉米根草螟Clemens(玉米根草螟)、早熟禾草螟Zincken(早熟禾草螟)、苹蠹蛾Linnaeus(苹果蠹蛾)、棉斑实蛾Boisduval(棉斑实蛾)、鼎点金刚钻Fabricius(埃及金刚钻)、Helicoverpa armigera Hübner(美洲棉铃虫)、玉米穗蛾Boddie(玉米穗蛾)、烟芽夜蛾Fabricius(烟夜蛾)、herpetogrammalicarsisalis Walker(草皮网虫)、葡萄小卷蛾Denis &Schiffermüller(葡萄小卷蛾)、棉红铃虫Saunders(棉红铃虫)、桔叶潜蛾Stainton(柑细潜蛾)、大菜粉蝶Linnaeus(大菜粉蝶)、菜粉蝶Linnaeus(菜粉蝶)、小菜蛾Linnaeus(小菜蛾)、甜菜夜蛾Hübner(甜菜夜蛾)、Spodoptera litura Fabricius(斜纹夜蛾、clustercaterpillar)、草地粘虫J.E.Smith(草地粘虫)、粉纹夜蛾Hübner(粉纹夜蛾)和Tuta absoluta Meyrick(番茄潜叶蛾))。本发明化合物还对半翅目害虫具有有生产意义的活性,所述半翅目害虫包括豌豆蚜Harris(豌豆蚜)、豆蚜Koch(豇豆蚜)、甜菜蚜Scopoli(蚕豆蚜)、棉蚜Glover(棉蚜、瓜蚜)、苹果蚜De Geer(苹果蚜)、绣线菊蚜Patch(绣线菊蚜)、茄沟无网蚜Kaltenbach(指顶花无网长管蚜)、草莓中瘤钉毛蚜Cockerell(草莓中瘤钉毛蚜)、Diuraphis noxiaKurdjumov/Mordvilko(俄国麦长管蚜)、苹粉红劣蚜Paaserini(苹粉红劣蚜)、苹果绵蚜Hausmann(苹果绵蚜)、桃粉大尾蚜Geoffroy(桃粉大尾蚜)、菜溢管蚜Kaltenbach(菜溢管蚜)、蔷薇麦蚜Walker(蔷薇麦蚜)、马铃薯长管蚜Thomas(茄长管蚜)、桃赤蚜Sulzer(桃赤蚜、桃蚜)、莴苣蚜Mosley(莴苣蚜)、瘿绵蚜属(根蚜和瘿蚜)、玉米溢管蚜Fitch(玉米溢管蚜)、禾谷溢管蚜Linnaeus(禾谷溢管蚜)、草间裂蚜茧峰Rondani(绿蚜)、麦长管蚜Fabricius(麦长管蚜)、苜蓿斑蚜Buckton(苜蓿斑蚜)、桔二岔蚜Boyer de Fonscolombe(柑二岔蚜)和桔二岔蚜Kirkaldy(热带柑二岔蚜);球蚜属(球蚜);美核桃根瘤蚜Pergande(美核桃根瘤蚜);甘薯粉虱(烟草粉虱、烟粉虱)、Bemisiaargentifolii Bellows & Perring(silverleaf whitefly)、桔黄粉虱Ashmead(柑黄粉虱)和温室白粉虱Westwood(温室白粉虱);蛋豆微叶蝉Harris(马铃薯微叶蝉)、灰稻虱Fallen(稻灰飞虱)、六点叶蝉Forbes(六点叶蝉)、黑尾叶蝉Uhler(大青叶蝉)、二点黑尾叶蝉Stl(二点黑尾叶蝉)、褐稻虱(褐稻虱)、玉米飞虱Ashmead(玉米飞虱)、白背飞虱Horvath(白背飞虱)、美洲稻飞虱Muir(美洲稻飞虱)、苹白小叶蝉McAtee(苹白小叶蝉)、红斑叶蝉属(葡萄二星斑叶蝉);十七年蝉Linnaeus(十七年蝉);吹绵蚧Maskell(吹绵蚧)、梨笠圆盾蚧Comstock(梨圆盾蚧);桔粉蚧Risso(柑粉蚧);粉蚧属(其它粉蚧);梨黄木虱Foerster(梨黄木虱)、柿木虱Ashmead(柿木虱)。这些化合物还对半翅目害虫具有活性,所述害虫包括喜绿蝽Say(喜绿蝽)、南瓜绿蝽De Geer(南瓜绿蝽)、麦长蝽Say(麦长蝽)、棉网蝽Fabricius(棉网蝽)、Cyrtopeltis modesta Distant(tomato bug)、棉黑翅红蝽Herrich-Schffer(棉黑翅红蝽)、褐臭蝽Say(褐臭蝽)、一点褐蝽Palisot de Beauvois(一点褐蝽)、Graptosthetus spp.(实蝽)、松子喙缘蝽Say(松子喙缘蝽)、牧草盲蝽Palisot de Beauvois(牧草盲蝽)、绿蝽Linnaeus(稻绿蝽)、美洲稻盾蝽Fabricius(美洲稻盾蝽)、马利筋长蝽Dallas(马利筋长蝽)、棉跳盲蝽Reuter(棉跳盲蝽)。由本发明化合物防治的其它昆虫目包括缨翅目(例如,苜蓿蓟马Pergande(苜蓿蓟马)、桔实蓟马Moulton(柑实蓟马)、Sericothripsvariabilis Beach(大豆蓟马)和棉蓟马Lindeman(棉蓟马);和鞘翅目(例如,马铃薯甲虫Say(马铃薯甲虫)、墨西哥豆瓢虫Mulsant(墨西哥豆瓢虫虫)和叩甲属、Athous或草金针虫属的切根虫)。
本发明化合物也可与一种或多种其它生物活性化合物或试剂(如,不同于式I的化合物、其N-氧化物或其盐)混合,形成具有更广谱农业应用的多组分农药,所述的一种或多种其它生物活性化合物或试剂包括杀虫剂、防霉剂、杀线虫剂、杀菌剂、杀螨剂、生长调节剂(如,生根刺激剂、化学绝育剂、化学信息剂、驱避剂、诱引剂、信息激素、助食剂)、其它生物活性化合物或昆虫病原细菌、病毒或真菌。因此,本发明组合物还可以含有至少一种其它生物活性化合物或试剂,所述其它生物活性化合物或试剂选自其它自杀虫剂、防霉剂、杀线虫剂、杀菌剂、杀螨剂、生长调节剂、生根刺激剂、化学绝育剂、化学信息剂、驱避剂、诱引剂、信息激素、助食剂和昆虫病原细菌、病毒或真菌。所述组合物优选还含有至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其它组分。
可以与本发明化合物一起配制的其它生物活性化合物或试剂的实例是:杀虫剂,例如,阿维菌素、高灭磷、吡虫青、齐墩螨素、艾扎丁、谷硫磷、氟氯菊酯、联苯肼酯、扑虱灵、克百威、氟唑虫青、定虫隆、毒死蜱、甲基毒死蜱、chromafenozide、clothianidin、百树菊酯、β-百树菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、氯氰菊酯、灭蝇胺、溴氰菊酯、丁醚脲、二嗪农、氟脲杀、乐果、噁茂醚、emamectin、硫丹、高氰戊菊酯、ethiprole、苯硫威、双氧威、甲氰菊酯、唑螨酯、杀灭菊酯、锐劲特、flonicamid、氟氰戊菊酯、氟胺氰菊酯、氟虫脲、地虫磷、特丁苯酰肼、氟铃脲、吡虫啉、噁二唑虫、丙胺磷、氟丙氧脲、马拉松、多聚乙醛、甲胺磷、杀扑磷、灭多虫、蒙五一五、甲氧滴滴涕、久效磷、甲氧苯酰肼、硝虫噻嗪、双苯氟脲、甲氨叉威、对硫磷、甲基对硫磷、氯菊酯、甲拌磷、伏杀磷、亚胺硫磷、磷胺、抗蚜威、丙溴磷、拒嗪酮、pyridalyl、蚊蝇醚、鱼藤酮、艾克敌、乙丙硫磷、双苯酰肼、伏虫隆、七氟菊酯、特丁磷、杀虫畏、thiacloprid、thiamethoxam、硫双威、杀虫双、四溴菊酯、敌百虫和杀虫隆;防霉剂,例如,噻二唑素、腈嘧菌酯、苯菌灵、灭瘟素、波尔多液(三碱式硫酸铜)、糠菌唑、氯环丙酰胺、敌菌丹、克菌丹、多菌灵、地茂散、百菌清、王铜、铜盐、cyflufenamid、清菌脲、环唑醇、环丙嘧啶、(S)-3,5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧代丙基)-4-甲基苯甲酰胺(RH7281)、diclocymet(S-2900)、哒菌清、氯硝胺、噁醚唑、(S)-3,5-二氢-5-甲基-2-(甲硫基)-5-苯基-3-(苯氨基)-4H-咪唑-4-酮(RP407213)、烯酰吗啉、dimoxystrobin、烯唑醇、烯唑醇-M、多果定、克瘟散、氧唑菌、噁唑酮菌、fenamidone、异嘧菌醇、腈苯唑、fencaramid(SZX0722)、拌种咯、苯锈啶、丁苯吗啉、薯瘟锡、毒菌锡、氟啶胺、氟噁菌、氟联苯菌(RPA 403397)、喹唑菌酮、氟硅唑、氟酰胺、粉唑醇、灭菌丹、藻菌磷、呋氨丙灵、呋吡唑灵(S-82658)、己唑醇、环戊唑醇、异稻瘟净、咪唑霉、稻瘟灵、春雷霉素、亚胺菌、代森锰锌、代森锰、mefenoxam、丙氧灭绣胺、甲霜灵、环戊唑菌、叉氨苯酰胺/叉氨苯酰胺(SSF-126)、腈菌唑、甲胂铁铵(甲基胂酸铁)、噁霜灵、戊菌唑、戊菌隆、噻菌灵、丙氯灵、百维灵、丙环唑、啶斑肟、pyraclostrobin、二甲嘧菌胺、咯喹酮、喹氧灵、螺噁茂胺、硫、戊唑醇、氟醚唑、涕必灵、溴氟唑菌、甲基硫菌灵、福美双、tiadinil、粉锈宁、羟锈宁、三环唑、trifloxystrobin、戊叉唑菌、有效霉素和烯菌酮;杀线虫剂,例如,涕灭威、甲氨叉威和克线磷;杀菌剂,例如,链霉素;杀螨剂,例如,虫螨脒、灭螨猛、乙酯杀螨醇、三环锡、开乐散、除螨灵、特苯噁唑、喹螨醚、杀螨锡、甲氰菊酯、唑螨酯、克螨特、哒螨酮和吡螨胺;和生物试剂,例如,苏金杆菌,包括ssp.Aizawai和kurstaki,苏金杆菌δ菌体内毒素,杆状病毒及昆虫病原细菌、病毒和真菌。本发明化合物及其组合物可以用于植物遗传转化以表达对无脊椎动物害虫有毒的蛋白(例如,苏金杆菌毒素)。外原无脊椎动物害虫防治化合物和组合物的作用可以与表达的毒性蛋白具有协同作用。
有关这些农业保护剂的综合性参考文献是The Pesticide Manual,12th Edition,C.D.Tomlin,E.,British Crop Protection Council,Farnham,Surrey,U.K.,2000。
本发明优选的组合物含有杀虫剂和杀螨剂作为其它生物活性化合物或试剂,所述杀虫剂和杀螨剂包括合成除虫菊酯,例如,氯氰菊酯、氯氟氰菊酯、百树菊酯、β-百树菊酯、高氰戊菊酯、杀灭菊酯和四溴菊酯;氨基甲酸酯,例如,苯硫威、灭多虫、甲氨叉威和硫双威;灭虫碱类,例如,clothianidin、吡虫啉和thiacloprid;神经元钠通道阻断剂,例如,噁二唑酮;杀虫大环内酯,例如,艾克敌105、阿维菌素、齐墩螨素和emamectin;γ-氨基丁酸(GABA)拮抗剂,例如,硫丹、ethiprole和锐劲特;杀虫脲,例如,氟虫脲和杀虫隆;保幼激素模拟物,例如,噁茂醚和蚊蝇醚;拒嗪酮;和虫螨脒。用于与本发明化合物混合的优选生物试剂包括苏金杆菌和苏金杆菌δ菌体内毒素以及遗传修饰的天然病毒杀虫剂,包括杆状病毒科杀虫剂和食虫真菌杀虫剂。
可用于本发明组合物和方法的最优选混合物包括本发明化合物与氟氯氰菊酯的混合物、本发明化合物与β-百树菊酯的混合物、本发明化合物与高氰戊菊酯的混合物、本发明化合物与灭多虫的混合物、本发明化合物与吡虫啉的混合物、本发明化合物与thiacloprid的混合物、本发明化合物与噁二唑虫的混合物、本发明化合物与齐墩螨素的混合物、本发明化合物与硫丹的混合物、本发明化合物与ethiprole的混合物、本发明化合物与锐劲特的混合物、本发明化合物与氟虫脲的混合物、本发明化合物与蚊蝇醚的混合物、本发明化合物与拒嗪酮的混合物、本发明化合物与虫螨醚的混合物、本发明化合物与苏金杆菌的混合物以及本发明化合物与苏金杆菌δ菌体内毒素的混合物。
在某些情况下,与其它具有类似防治范围但作用模式不同的无脊椎动物害虫防治化合物或试剂组合,特别有利于抗性管理。因此,本发明组合物和方法还可以含有至少一种具有类似防治范围但作用模式不同的生物有效量无脊椎动物害虫防治化合物或试剂。使遗传修饰植物(表达植物保护化合物(如,蛋白质))或植物场所与本发明的生物有效量化合物接触,也可以获得较宽的植物保护范围并有利于抗性管理。
在农艺和/或非农艺应用中,通过将本发明的一种或多种生物有效量化合物或组合物施用于害虫环境(包括农艺和/或非农艺侵染场所)、待保护的区域或直接施用于待防治害虫,防治至少一种无脊椎动物害虫。因此,本发明还包括一种防治农艺和/或非农艺环境中的至少一种无脊椎动物害虫的方法,包括使无脊椎动物害虫或其环境与本发明的一种或多种生物有效量化合物接触,或与含有至少一种所述化合物的生物有效量组合物接触,或与含有至少一种所述化合物和至少一种其它生物有效量的生物活性化合物或试剂的生物有效量组合物接触。含有至少一种本发明化合物和至少一种其它生物活性化合物或试剂的合适组合物的实例包括粒状组合物,其中,其它生物活性化合物与本发明化合物存在于同一颗粒上,或者,其它生物活性化合物与本发明化合物存在于单独分开的颗粒上。
优选的接触方法是喷雾。或者,可以将含本发明化合物的粒状组合物施用于植物叶面或土壤中。以土壤浸润液体制剂、土壤粒剂、苗箱施药或移植物浸液的形式施用含本发明化合物的组合物,使植物与所述组合物接触,通过植物吸收也能够有效递送本发明化合物。本发明化合物还可以通过向侵染场所局部施用本发明化合物起效。其它接触方法包括:通过直接喷雾和滞留喷雾、空中喷洒、胶化、种子包衣、微囊包封、内吸摄入、诱饵、耳标、丸剂、喷雾器、熏蒸剂、气溶胶、粉剂和许多其它方法来施用本发明化合物或组合物。也可以将本发明化合物浸渍到制造无脊椎动物防治装置(如,昆虫采集网)的材料中。
可以将本发明化合物掺入供无脊椎动物采食的诱饵中或加入诸如诱捕器之类的装置内。在土壤昆虫的防治中,含有0.01-5%活性组分、0.05-10%保湿剂和40-99%植物细粉的颗粒或饵剂以极低的施用量起效,特别是以经摄食而不经直接接触致死的活性组分剂量起效。
可以施用纯态的本发明化合物,但最经常以制剂的形式施用,所述制剂含有一种或多种化合物和适当的载体、稀释剂和表面活性剂以及根据预期的最终用途还可能混有食物。优选的施用方法包括喷洒化合物的水分散体或精制油溶液。与喷雾油、喷雾油浓缩物、粘展剂、辅助剂、其它溶剂和诸如胡椒基丁醚的增效剂混合使用通常会增强化合物的效力。
实现有效防治所需的施用量(即,“生物有效量”)取决于下列因素:例如,欲防治的无脊椎动物种类、害虫生命周期、生命期、害虫的大小、场所、季节、宿主作物或动物、进食行为、交配行为、环境湿度、温度等。正常情况下,每公顷大约0.01-2kg活性组分施用量足以防治农艺生态系统中的害虫,但低至0.0001kg/公顷可能已足够,或者,可能需要多至8kg/公顷的用量。对于非农艺应用,有效用量为大约1.0-50mg/公顷,但低至0.1mg/公顷的用量可能已足以,或者可能需要多至150mg/公顷的用量。对于无脊椎动物害虫的预定防治目标,本领域技术人员能够容易地确定其所需的生物有效量。
以下试验表明了本发明化合物对特定害虫的防治效力。“防治效力”表示抑制无脊椎动物害虫发育(包括致死),使其进食明显减少。但是,本发明化合物所提供的害虫防治保护作用不限于这些种类。有关化合物的描述见索引表A和B。索引表中使用的缩写如下:t是叔,n是正,i是异,c是环,s是仲,Me是甲基,Et是乙基,Pr是丙基,i-Pr是异丙基,Bu是丁基,n-butyl是丁基,t-Bu是叔丁基,Hex是己基,c-Hex是环己基,OMe是甲氧基,OEt乙氧基,SMe是甲硫基,SEt是乙硫基,CN是氰基和NO2硝基。缩写“Ex.”表示“实施例”,其后的数字表示在该实施例中被制备出的化合物。
索引表A
化合物 | R 2a | R 2b | R 2c | R 7 | U | m.p.℃ |
1(Ex.1)234567(Ex.2)8(Ex.3)126127128 | 2-Me2-Et2-Me2-Me2-Me2-Me2-F2-Cl2-Cl2-F2-Me | 6-ClHHH4-MeH4-F4-Cl4-CN4-FH | H6-Et6-OMe6-i-PrHH6-BrH6-Cl6-BrH | CF3CF3CF3CF3CF3BrBrCF3ClClCF3 | CHCHCHCHCHCHCHCHCHCHN | 212-213185-195150-160145-155110-120180-181138-139oil193-194147-148145-147 |
索引表B(实施例4)
化合物 | R 1 | R 2a | R 2b | R 2c | 测得的M+H |
910111213141516171819202122232426272829303132333435 | HHHHHHHHHHHHHHHHHHHHHHHHHH | 2-NO22-Br2-Br2-F2-F2-Cl2-Cl2-Cl2-Cl2-Me2-Me2-Me2-Me2-Me2-Me2-Et2-Br2-Cl2-CF32-OMe2-Br2-Cl2-Me2-Cl2-Cl2-Br | H4-NO24-Me4-FH4-ClH3-MeH4-Me4-MeHHHHH4-F4-MeHH4-i-Pr4-CN4-CN4-CF34-Cl4-c-Hex | 6-NO26-Br6-Br6-F6-F6-Cl6-Cl6-Cl6-Me6-NO26-Me6-NO26-i-Pr6-Me6-Et6-Et6-Br6-Me6-F6-Me6-Br6-Cl6-Cl6-Br6-Me6-Br | 457.00569.96538.95421.06403.03470.98437.00449.02415.03440.07409.09426.05423.10395.07409.09423.10542.83429.05453.06411.10566.95460.01440.07548.98449.02606.98 |
化合物 | R 1 | R 2a | R 2b | R 2c | 测得的M+H |
36373839404142434445464748495051525354555657585960616263646566676869707172 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | 2-Br2-NO22-OMe2-OEt2-Ph2-SMe2-CF32-i-Pr2-Me2-Me2-Me2-CH2Ph2-Et3-CN3-Br3-F3-Cl3-Cl3-Cl3-I3-NO23-OMe3-OEt3-SMe3-CF33-Me4-CN4-Br2-Me4-F4-Cl3-CF34-I4-NO24-OPh4-OMe4-OEt | 4-CF3HHHHHHHH4-Me5-MeHHHHHH4-Cl5-ClHHHHHHHHH4-BrHH4-ClHHHHH | 6-BrHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHHH | 592.88412.12397.15411.16443.17413.13435.14409.19381.15395.17395.17457.22395.18392.15445.08385.15401.14435.12435.12493.13412.19397.22411.24413.20435.06381.18393.10447.00461.11385.07401.04469.02492.97412.06459.09397.08411.08 |
化合物 | R 1 | R 2a | R 2b | R 2c | 测得的M+H |
7374757677787980818283848687888990919293949596979899100101102103104105106107108109111 | HHHHHHHHHHHHHHHHHHHHHHHHHHHHMeCH2CH2CNEtMeEtMeEtn-BuH | 4-Ph4-SMe4-i-Bu4-i-Pr4-Me4-CH2CN4-n-Pr2-OMe2-OMe3-OMe3-OMe2-n-Pr2-OPh2-OCF34-OCF33-OCF33-OPh2-Br2-OMe2-CF34-CF34-OCF3H2-CH2CN2-t-Bu2-OCF2H2-Br2-Cl2-N-哌啶4-ClH2-NO2HH4-Me2-MeHH | HHHHHHH5-OMe4-OMe5-OMe4-OMeHHHHHH4-CF35-CF34-BrHHHHH2-Cl4-CF3HHHHHHHHHH | HHHHHHHHHH5-OMeHHHHHHHHHHHHHHHHHHHHHHHHHH | 443.08413.03423.08409.07381.04406.04409.06427.03427.03427.04457.04409.06459.02450.98450.98450.97459.02512.89464.99512.90434.99433.00406.04423.08433.01480.92469.00450.12415.05420.09440.09381.12395.11395.11409.12423.15367.22 |
化合物 | R 1 | R 2a | R 2b | R 2c | 测得的M+H |
112113114115116117118119120121122123124125 | HHHHHHHHHHHHHH | 2-CN2-Br2-Br2-Br2-F2-F2-F2-Cl2-Cl2-Cl2-Cl2-Cl2-Cl2-I | HH4-Me5-CF3H4-F5-FH4-Br4-Cl4-Me5-Cl5-CF3H | HHHHHHHHHHHHHH | 392.13447.06461.08515.06385.13403.12403.12401.10481.02437.07415.12437.09469.10493.05 |
本发明生物实施例
试验A
为了评估对小菜蛾(小菜蛾)的防治作用,试验装置由内有12-14天大的萝卜植物的开顶小容器构成。使用钻心采样器,从一片上面带有许多生长幼虫的硬化昆虫食物上取出芯子,并将含有幼虫和食物的该芯子移至试验装置中,使该装置预先被该片昆虫食物上的10-15只新孵化幼虫侵害。将以食物芯子形式移至试验装置上的幼虫干透。
除非另有说明,使用含有10%丙酮、90%水和300ppm X-77Spreader Lo-Foam Formula非离子表面活性剂(Loveland Industries,Inc.Greeley,Colorado,USA)的溶液,配制试验化合物,其中所述表面活性剂含有烷芳基聚氧乙烯、游离脂肪酸、乙二醇和异丙醇。通过带有1/8JJ定制体(Spraying Systems Co.Wheaton,Illinois,USA)的SUJ2喷管,以1mL液体施用所配制的化合物,其中,1/8JJ定制体安置于各试验装置顶部上方1.27cm(0.5英寸)处。在这些试验中,所有试验化合物以250ppm(或更低)喷雾,并重复3次。喷雾配制的试验化合物后,使各试验装置干燥1小时,然后将黑色隔离帽置于顶部。将试验装置在25℃和70%相对湿度的生长室内保持6天。然后,根据所消耗的植物,目测评估植物侵食损害。
在试验的化合物*中,以下化合物提供了极优良至优秀的植物保护水平(0-1、10%或更低的侵食损害率):1**、7***、8***、126***、127***和128***。
试验B
为了评估对秋粘虫(草地粘虫)的防治作用,试验装置由内有4-5-天大的玉米(玉蜀黍)植物的开顶小容器构成。使该装置预先被一片昆虫食物上的10-15只1天大的幼虫侵害(使用钻心采样器)。
如试验A所述,配制试验化合物并以250ppm(或更低)喷雾。重复3次施药。喷雾后,在生长室内保持试验装置,然后,如试验A所述进行目测评估。
在试验的化合物*中,以下化合物提供了优秀的植物保护水平(10%或更低的侵食损害率):1**、6***、7***、8***和127***。
试验C
为了评估对烟夜蛾(烟夜蛾)的防治作用,试验装置由内有6-7-天大的棉花植物的开顶小容器构成。使该装置预先被一片昆虫食物上的8只2天大的幼虫侵害(使用钻心采样器)。
如试验A所述,配制试验化合物并以250ppm(或更低)喷雾。重复3次施药。喷雾后,在生长室内保持试验装置,然后,如试验A所述进行目测评估。
在试验的化合物*中,以下化合物提供了极优良至优秀的植物保护水平(20%或更低的侵食损害率):7***和8***。
试验D
为了评估对甜菜夜蛾(甜菜夜蛾)的防治作用,试验装置由内有4-5-天大的玉米植物的开顶小容器构成。使该装置预先被一片昆虫食物上的10-15只1天大的幼虫侵害(使用钻心采样器)。
如试验A所述,配制试验化合物并以250ppm(或更低)喷雾。重复3次施药。喷雾后,在生长室内保持试验装置,然后,如试验A所述进行目测评估。
在试验的化合物*中,以下化合物提供了极优良至优秀的植物保护水平(20%或更低的侵食损害率):7***。
试验E
作为对秋粘虫(秋粘虫)防治作用的另一个评估试验,试验装置由装满175μL鳞翅目昆虫大豆小麦胚食物的微量滴定板构成。各孔用在75/25丙酮/水中配制的25μL 1050μM(或更低浓度)试验化合物处理。施用化学农药后,微量滴定板在通风室中干燥24小时。在24小时干燥期后,用秋粘虫卵侵害滴定板然后密封。在27℃(白天)70%相对湿度条件下保存试验装置6天。根据昆虫杀死评估活性。
在试验的化合物中,以下化合物提供了极优良至优秀的秋粘虫防治水平(90%或更多活昆虫被杀死):10、11、12、13、14、15、17、19、20、22、26、27、28、29、31、32、34、44、64、69、91、94、99、100、114、115、120和121。
*在该试验中未对索引表B中的化合物9-125进行评估。
**以250ppm进行试验。
***以50ppm进行试验。
Claims (14)
1.式I化合物、其N-氧化物或其盐,
其中,
A是O或S;
B是苯环或吡啶环,各环被1-5个R2取代;
J是选自J-1、J-2、J-3、J-4、J-5和J-6的吡唑或吡咯杂环系;
和
R1是H;或各自任选被一个或多个取代基取代的C1-C6烷基、C2-C6烯基、C2-C6炔基或C3-C6环烷基,所述取代基选自:卤素、CN、NO2、羟基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C2-C4烷氧基羰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
R1是C2-C6烷基羰基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基或C3-C8二烷基氨基羰基;
各个R2独立地选自:H、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C6卤代环烷基、C2-C4氰基烷基、卤素、CN、NO2、哌啶、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚硫酰基、C1-C4卤代烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基和C3-C6环烷基氨基;或
各个R2独立地选自:苯基环、苄基环或苯氧基环,各个环任选被一个或多个取代基取代,所述取代基选自:C1-C4烷基、C2-C4烯基、C2-C4炔基、C3-C6环烷基、C1-C4卤代烷基、C2-C4卤代烯基、C2-C4卤代炔基、C3-C6卤代环烷基、卤素、CN、NO2、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4烷基氨基、C2-C8二烷基氨基、C3-C6环烷基氨基、C4-C7(烷基)环烷基氨基、C2-C6烷氧基羰基、C2-C6烷基氨基羰基和C3-C8二烷基氨基羰基;
R5是
各个R6、R6a和R7独立地选自:H、C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、卤素、CN、C1-C4烷氧基、C1-C4烷硫基、C1-C4卤代烷氧基和C1-C4卤代烷硫基;和
R8是H、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6卤代烯基、C3-C6炔基、C3-C6卤代炔基或C1-C4卤代烷氧基。
2.根据权利要求1的化合物,其中J是J-1、J-2、J-3或J-6。
3.根据权利要求2的化合物,其中:
A是O;
R1是H;
1-3个R2基团不是H并独立地选自C1-C6烷基、C1-C6卤代烷基、C2-C4氰基烷基、卤素、CN、NO2、哌啶、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基亚硫酰基、C1-C4烷基磺酰基、C1-C4卤代烷硫基、C1-C4卤代烷基亚硫酰基和C1-C4卤代烷基磺酰基;和
至少一个如最接近的上文定义的R2位于NR1C(=A)J部分的邻位。
4.根据权利要求3的化合物,其中两个R2位于NR1C(=A)J部分的邻位。
5.根据权利要求3的化合物,其中:
R6是H、C1-C4烷基、C1-C4卤代烷基、卤素或CN;和
R7是H、CH3、CF3、CH2CF3、CHF2、OCH2CF3、OCHF2或卤素。
6.根据权利要求5的化合物,其中:
J是J-1;
R6是Cl或Br;和
R7是卤素、OCH2CF3、OCHF2或CF3。
7.根据权利要求5的化合物,其中:
J是J-2;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
8.根据权利要求5的化合物,其中:
J是J-3;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
9.权利要求5的化合物,其中:
J是J-5;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
10.根据权利要求5的化合物,其中:
J是J-6;
R6是Cl或Br;和
R8是CH2CF3或CHF2。
11.一种组合物,含有至少一种权利要求1的化合物和至少一种选自表面活性剂、固体稀释剂和液体稀释剂的其它组分。
12.根据权利要求11的组合物,还含有至少一种其它生物活性化合物或试剂。
13.一种防治至少一种无脊椎动物害虫的方法,包括将无脊椎动物害虫或其环境与生物有效量的至少一种权利要求1化合物接触或与生物有效量的权利要求11的组合物接触。
14.根据权利要求13的方法,其中所述组合物还含有至少一种用于防治无脊椎动物害虫的其它生物有效量生物活性化合物或试剂。
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- 2003-06-10 EP EP03739103A patent/EP1511733A2/en not_active Withdrawn
- 2003-06-10 CN CNB038127318A patent/CN100335477C/zh not_active Expired - Fee Related
- 2003-06-10 KR KR10-2004-7020187A patent/KR20050009747A/ko not_active Application Discontinuation
- 2003-06-10 AU AU2003245464A patent/AU2003245464A1/en not_active Abandoned
- 2003-06-10 WO PCT/US2003/018609 patent/WO2003106427A2/en active Application Filing
- 2003-06-10 US US10/514,183 patent/US7754738B2/en not_active Expired - Fee Related
- 2003-06-10 BR BR0311707-3A patent/BR0311707A/pt not_active IP Right Cessation
- 2003-06-10 JP JP2004513260A patent/JP4287816B2/ja not_active Expired - Fee Related
- 2003-06-10 MX MXPA04012214A patent/MXPA04012214A/es not_active Application Discontinuation
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CN103068820A (zh) * | 2010-06-15 | 2013-04-24 | 拜耳知识产权有限责任公司 | 新的邻位取代的芳基酰胺衍生物 |
CN102391248A (zh) * | 2011-09-29 | 2012-03-28 | 青岛科技大学 | 邻氨基苯甲腈类化合物及其制法与用途 |
WO2013044791A1 (zh) * | 2011-09-29 | 2013-04-04 | 杭州宇龙化工有限公司 | 邻氨基苯甲腈类化合物及其制备方法与它们的用途 |
CN102391248B (zh) * | 2011-09-29 | 2016-05-11 | 杭州宇龙化工有限公司 | 邻氨基苯甲腈类化合物及其制法与用途 |
CN109970707A (zh) * | 2012-02-07 | 2019-07-05 | 拜耳知识产权有限责任公司 | 取代的邻氨基苯甲酸衍生物的制备方法 |
CN104271562A (zh) * | 2012-05-07 | 2015-01-07 | 株式会社经农 | 经氨基甲酸酯取代的二氨基芳基衍生物及包含所述衍生物的杀虫组合物 |
CN104271562B (zh) * | 2012-05-07 | 2017-03-15 | 株式会社经农 | 经氨基甲酸酯取代的二氨基芳基衍生物及包含所述衍生物的杀虫组合物 |
CN105541794A (zh) * | 2016-01-08 | 2016-05-04 | 南开大学 | 含有七氟异丙基的吡啶基吡唑酰胺类衍生物及其应用 |
CN105712975B (zh) * | 2016-01-26 | 2018-10-12 | 西安近代化学研究所 | 一种含有1,2,3-三唑环的吡唑酰胺化合物和应用 |
Also Published As
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JP4287816B2 (ja) | 2009-07-01 |
US7754738B2 (en) | 2010-07-13 |
MXPA04012214A (es) | 2005-02-25 |
BR0311707A (pt) | 2005-03-15 |
EP1511733A2 (en) | 2005-03-09 |
AU2003245464A1 (en) | 2003-12-31 |
WO2003106427A3 (en) | 2004-06-24 |
JP2005532367A (ja) | 2005-10-27 |
KR20050009747A (ko) | 2005-01-25 |
US20060167060A1 (en) | 2006-07-27 |
CN100335477C (zh) | 2007-09-05 |
WO2003106427A2 (en) | 2003-12-24 |
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