CN101146777B - 羧酰苯胺杀微生物剂 - Google Patents
羧酰苯胺杀微生物剂 Download PDFInfo
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- CN101146777B CN101146777B CN2006800092863A CN200680009286A CN101146777B CN 101146777 B CN101146777 B CN 101146777B CN 2006800092863 A CN2006800092863 A CN 2006800092863A CN 200680009286 A CN200680009286 A CN 200680009286A CN 101146777 B CN101146777 B CN 101146777B
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
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- A—HUMAN NECESSITIES
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- 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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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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
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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
- A01N43/48—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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- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
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- A—HUMAN NECESSITIES
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
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Abstract
通式I化合物适于用作杀微生物剂,其中的取代基定义如权利要求1所述。
Description
本发明涉及新的杀微生物活性,尤其是杀真菌活性的羧酰苯胺。并且涉及制备这些化合物的中间体,包含这些化合物的组合物和它们在农业或园艺中控制或预防病源微生物,尤其是真菌侵染的用途。
WO04/018438和EP-0-589-301中描述了羧酰苯胺具有杀微生物活性。
已经发现具有特定邻位、间位-二取代模式的新羧酰苯胺具有杀微生物活性。
本发明因此提供了式I化合物
其中
R1是C1-C4烷基,C2-C4烯基或C2-C4炔基;或
R1是被卤素,羟基,氰基,C1-C4烷氧羰基,甲酰基,硝基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4卤代烷硫基,HC(OR4)=N-和/或R5R6NN=C(H)-单或多取代的C1-C4烷基、C2-C4烯基或C2-C4炔基;
R4,R5和R6彼此独立地各自是氢或C1-C4烷基;
R2是C1-C6烷基;或
R2是被卤素,羟基,氰基,C1-C4烷氧羰基,甲酰基,硝基,C1-C4烷氧基,C1-C4卤代烷氧基,C1-C4烷硫基,C1-C4卤代烷硫基,HC(OR7)=N-和/或R8R9NN=C(H)-单或多取代的C1-C6烷基;
R7,R8和R9彼此独立地各自是氢或C1-C4烷基;
R3是氢或卤素;
A是A1
其中
R11,R12和R13彼此独立地各自选自氢,卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基和C1-C4卤代烷氧基-C1-C4烷基,条件是R11,R12和R13至少其中之一不是氢;
或A是A2
其中
R21,R22和R23彼此独立地各自是氢,卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基,条件是R11,R12和R13至少其中之一不是氢;
或A是A3
其中
R31和R32彼此独立地各自是氢,卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基,条件是R31和R32至少其中之一不是氢;
或A是A4
其中
R41和R42彼此独立地各自是氢,卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基,条件是R41和R42至少其中之一不是氢;
或A是A5
其中
R51是卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基;
或A是A6
其中
R61是卤素,氰基,硝基,C1-C4烷基,C1-C4卤代烷基,C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基;
和这些化合物的互变异构体/同分异构体/对映体。
出现在取代基中的烷基可以是直链或支链,如甲基,乙基,正丙基,正丁基,正戊基,正己基,异丙基,正丁基,仲丁基,异丁基或叔丁基。烷氧基、烯基和炔基衍生自所述的烷基。烯基和炔基可以是单或双不饱和的。
卤素通常是指氟,氯,溴或碘,优选氟,溴或氯。这还相应适用于卤素与其它含义结合在一起的情况如卤代烷基或卤代烷氧基。
卤代烷基优选具有一个至四个碳原子的链长。卤代烷基是,例如,氟甲基,二氟甲基,三氟甲基,氯甲基,二氯甲基,三氯甲基,2,2,2-三氟乙基,2-氟乙基,2-氯乙基,五氟乙基,1,1-二氟-2,2,2-三氯乙基,2,2,3,3-四氟乙基和2,2,2-三氯乙基;优选三氯甲基,二氟氯甲基,二氟甲基,三氟甲基和二氯氟甲基。
合适的卤代烯基是被卤素单或多取代的烯基,卤素是氟,氯,溴和碘,尤其是氟和氯,如2,2-二氟-1-甲基乙烯基,3-氟丙烯基,3-氯丙烯基,3-溴丙烯基,2,3,3-三氟丙烯基,2,3,3-三氯丙烯基和4,4,4-三氟丁-2-烯-1-基。
合适的卤代炔基是,例如,被卤素单或多取代的炔基,卤素是溴和碘,尤其是氟和氯,如3-氟丙炔基,3-氯丙炔基,3-溴丙炔基,3,3,3-三氟丙炔基和4,4,4-三氟丁-2-炔-1-基。
烷氧基是,例如,甲氧基,乙氧基,丙氧基,异丙氧基,正丁氧基,仲丁氧基和叔丁氧基;优选甲氧基和乙氧基。
卤代烷氧基是,例如,氟代甲氧基,二氟甲氧基,三氟甲氧基,2,2,2-三氟乙氧基,1,1,2,2-四氟乙氧基,2-氟乙氧基,2-氯乙氧基,2,2-三氟乙氧基和2,2,2-三氯乙氧基;优选二氟甲氧基,2-氯乙氧基和三氟甲氧基。烷硫基是,例如,甲硫基,乙硫基,丙硫基,异丙硫基,正丁硫基,异丁硫基,仲丁硫基或叔丁硫基,优选甲硫基和乙硫基。
烷氧基烷基是,例如,甲氧甲基,甲氧乙基,乙氧甲基,乙氧乙基,正丙氧甲基,正丙氧乙基,异丙氧甲基或异丙氧乙基。
本发明上下文中的“单或多取代”,如在取代基R1和R2的定义中,通常表示单次取代至九次取代,优选单次取代至五次取代,更优选单取代、二取代或三取代。
式I可以以不同互变异构体的形式出现,如II和III:
本发明包括所有这些互变异构体。
优选式I化合物,其中R1是C1-C4烷基,C2-C4烯基或C2-C4炔基;或R1是被卤素、羟基、甲氧基、三氟甲氧基、二氟甲氧基、氰基和/或硝基单取代或多取代的C1-C4烷基、C2-C4烯基或C2-C4炔基。更优选的式I化合物中的R1是C1-C4烷基、C2-C4烯基或C2-C4炔基。最优选的式I化合物中的R1是甲基、乙基或乙烯基。
还优选式I化合物,其中R2是C2-C5烷基;或R2是被卤素、羟基、氰基、C1-C4烷氧基羰基、甲酰基、硝基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷硫基、C1-C4卤代烷硫基、HC(OR7)=N-和/或R8R9NN=C(H)-单取代或多取代的C2-C5烷基。更优选R1是乙基、异丙基、丁基、异丁基、戊基、新戊基的式I化合物。
还优选式I化合物,其中R2是甲基。
特别有利的式I化合物是其中的R3是氢或氟的化合物。在这些优选的化合物中R3是氢。
优选式I化合物,其中R11,R12和R13彼此独立地各自选自氢,卤素,C1-C4烷基,C1-C4卤代烷基和C1-C4烷氧基-C1-C4烷基;条件是R11,R12和R13至少其中之一不是氢。更优选R11,R12和R13彼此独立地各自选自氢,卤素,甲基,C1-C2卤代烷基和甲氧甲基;条件是R11,R12和R13至少其中之一不是氢。
优选式I化合物,其中R21,R22和R23彼此独立地各自选自氢,卤素,C1-C4烷基,C1-C4卤代烷基和C1-C4烷氧基-C1-C4烷基;条件是R21,R22和R23至少其中之一不是氢。更优选R21,R22和R23彼此独立地各自选自氢,卤素,甲基,C1-C2卤代烷基和甲氧甲基;条件是R21,R22和R23至少其中之一不是氢。
优选式I化合物,其中R31和R32彼此独立地各自选自氢,卤素,C1-C4烷基,C1-C4卤代烷基和C1-C4烷氧基-C1-C4烷基;条件是R31和R32至少其中之一不是氢。更优选R31,R32和R33彼此独立地各自选自氢,卤素,甲基,C1-C2卤代烷基和甲氧甲基;条件是R31和R32至少其中之一不是氢。
优选式I化合物,其中R41和R42彼此独立地各自选自氢,卤素,C1-C4烷基,C1-C4卤代烷基和C1-C4烷氧基-C1-C4烷基;条件是R41和R42至少其中之一不是氢。更优选R41和R42彼此独立地各自选自氢,卤素,甲基,C1-C2卤代烷基和甲氧甲基;条件是R41和R42至少其中之一不是氢。
优选式I化合物,其中R51和R52彼此独立地各自选自氢,卤素,C1-C4烷基,C1-C4卤代烷基和C1-C4烷氧基-C1-C4烷基;条件是R51和R52至少其中之一不是氢。更优选R51和R52彼此独立地各自选自氢,卤素,甲基,C1-C2卤代烷基和甲氧甲基;条件是R51和R52至少其中之一不是氢。
优选A是A1,A2,A4,A5或A6。在另一优选化合物组中,A是A1,A2,A3,A4或A6。在一更优选的化合物组中,A是A1,A2,A4或A6。最优选A是A1,A2或A4。
在特别优选的化合物组中,A是A1,其中R13是氢。
在另一个特别优选的化合物组中,A是A1,其中R11是C1-C4烷基或C1-C4卤代烷基;R12是C1-C4烷基;和R13是氢或卤素。
在另一个特别优选的化合物组中,A是A2,其中R21是C1-C4烷基或C1-C4卤代烷基;R22是C1-C4烷基;和R23是氢或卤素。
在又一个特别优选的化合物组中,A是A3,其中R31是C1-C4烷基或C1-C4卤代烷基;和R32是C1-C4烷基。
在又一个特别优选的化合物组中,A是A4,其中R41是C1-C4烷基或C1-C4卤代烷基;和R42是C1-C4烷基。
在又一个特别优选的化合物组中,A是A5,其中R51是卤素或C1-C4卤代烷基。
在又一个特别优选的化合物组中,A是A6,其中R61是C1-C4烷基或C1-C4卤代烷基。
式I化合物可以通过式Ia化合物
A-C(=O)-R*(Ia),
其中A的定义同式I,R*是卤素,羟基或C1-6烷氧基,优选氯;与式II化合物在碱的存在下在溶剂中反应制备
其中R1,R2和R3的定义同式I;碱如三乙胺,Hunig碱,碳酸氢钠,碳酸钠,碳酸钾,吡啶或喹啉,优选三乙胺,溶剂如乙醚,TBME,THF,二氯甲烷,氯仿,DMF或NMP,10分钟至48小时,优选12至24小时,及0℃至回流温度,优选20至25℃。
式II中间体化合物是新化合物
其中R1,R2和R3定义同式I;专门为制备式I而开发的。因此,它们也构成本发明主题的一部分。
在优选的式II中间体中,R1是C1-C4烷基,C2-C4烯基或C2-C4炔基;或R1是被卤素、羟基、甲氧基、三氟甲氧基、二氟甲氧基、氰基和硝基单或多取代的C1-C4烷基、C2-C4烯基或C2-C4炔基。更优选的式II中间体中,R1是C1-C4烷基,C2-C4烯基或C2-C4炔基。最优选的式II中间体中,R1是甲基,乙基或乙烯基。还优选式II中间体,其中R2是甲基,乙基,异丙基,丁基,异丁基,戊基,新戊基。特别有利的式II中间体中,R3是氢或氟。优选式II中间体,其中R3是氢。
式II中间体,其中R1,R2和R3的定义同式I;可以按照以下反应方案来制备(方案1A,1B和1C)。
式IIa中间体(式II中间体,其中R1是甲基)可以通过反应方案1A来制备。
方案1A:
第一步,式III化合物与硫酸和亚硝酸钠反应形成重氮盐。用溴化铜(I)处理该重氮盐得到式IV芳基溴。在Béchamp条件下用铁还原式IV化合物并且用甲酸甲酰化生成的氨基得到式V的甲酰苯胺。式V化合物与强碱如丁基锂反应形成双负离子,该双负离子接着甲基化成式VI化合物。用氢氧化钾将式VI化合物进行碱水解得到式IIa苯胺。
式IIb中间体(式II中间体,其中R1是乙基或丙基)或式IIc(式II中间体,其中R1是乙烯基或烯丙基)可以按照反应方案1B来制备。
方案1B:
第一步中,式III化合物与硫酸和亚硝酸钠反应形成重氮盐。用碘化钾处理该重氮盐得到式VII芳基碘(常规“Sandmeyer”反应).下一步中,VII芳基碘用标准“Fu”条件(如三丁基乙烯基锡烷、钯催化剂和氟化铯)进行“Stille”偶合反应得到乙烯基取代的式VIII芳香化合物。式VIII芳香化合物既可以转化成部分还原的式IIc化合物(用精炼铁作为还原剂)或在完全还原(用钯金属催化剂)后转化成双烷基化的式IIb化合物。
式IIb中间体(式II中间体,其中R1是乙基或丙基)或式IId(式II中间体,其中R1是乙烯基或烯丙基)可以按照反应方案1C来制备。
方案1C:
在钯催化剂和氟化铯(改进的“Stille”偶合)的存在下,用三丁基乙炔基锡烷处理上述式VII碘化物得到在芳环上具有乙炔部分的式IX化合物。式VIII化合物既可以转化成部分还原(用精炼铁作为还原剂)的式IId化合物或完全还原(用钯金属催化剂,如披钯炭)后被转化为双烷基化的式IIb化合物。
通式化合物III、IV和VII的合成可以使用已公开的类似方法来完成:Rec.Trav.Chim.1952,71,321;J.Chem.Soc.Perkin.Trans2,1973,6,848;和Acta Chem.Scandinavica1976,30B,141。
式Ia化合物是已知的,并且部分可以市购得到。它们可以仿照WO00/09482,WO02/38542,WO04/018438,EP-0-589-301,WO93/11117和Arch.of Pharm.Res.2000,23(4),315-323中描述的方法来制备。
有大量合适的已知标准方法来制备根据R1,R2,R3和A的定义进一步官能化的所有其它式I化合物。如烷基化、卤化、酰化、酰胺化、肟化、氧化和还原化。根据中间体上取代基的性质(反应性)来选择合适的制备方法。
生成式I化合物的反应在质子惰性的有机溶剂中进行是有利的。所述溶剂有烃类,如苯,甲苯,二甲苯或环己烷,氯代烃类如二氯甲烷,三氯甲烷,四氯化碳或氯苯,醚类如乙醚,乙二醇二甲醚,二甘醇二甲醚,四氢呋喃或二氧己环,腈类如乙腈或丙腈,酰胺如N,N-二甲基甲酰胺,二乙基甲酰胺或N-甲基吡咯烷酮。反应温度在-20℃至+120℃之间是有利的。通常,反应是轻微放热的,并且,一般情况下,这些反应可在室温下进行。为了缩短反应时间或启动反应,反应混合物可以短暂地加热至混合物的沸点。还可以通过滴加几滴碱作为反应催化剂来缩短反应时间。合适的碱有,特别是,叔胺类如三甲胺,三乙胺,奎宁环,1,4-二氮杂二环[2.2.2]辛烷,1,5-二氮杂二环[4.3.0]壬-5-烯或1,5-二氮杂二环[5.4.0]十一碳-7-烯。然而,无机碱如氢化物,例如氢化钠或氢化钙,氢氧化物,如氢氧化钠或氢氧化钾,碳酸盐如碳酸钠和碳酸钾,或碳酸氢盐如碳酸氢钾和碳酸氢钠也可以用作碱。碱可以直接使用或与催化量的相转移催化剂,如冠醚,特别是18-冠-6,或四烷基铵盐一起使用。
式I化合物可以通过浓缩和/或蒸发溶剂的常规方式来分离,和重结晶或在不易溶解的溶剂如醚类、芳香烃或氯代烃类中研磨来纯化。
式I化合物和,适当的话,其互变异构体,可以以一种可能的异构体或异构体混合物形式存在。例如纯的异构体,如对映体和/或非对映体或异构体混合物,例如对映体混合物,如外消旋体,非对映体混合物或外消旋体混合物,这取决于分子中不对称碳原子的数量、绝对和相对构型和/或取决于分子中非芳香性双键的构型;本发明涉及所述化合物的纯的异构体,也涉及所有可能的异构体混合物,并且即使在所有情况下没有详细提及其立体化学细节,在上下文中的所有情况下也应该如此理解。
根据所选择的起始原料和步骤的不同,获得的式I化合物的非对映体混合物或外消旋体混合物可以依据各成分的物理化学性能的差异用已知方法分离成纯的非对映体或外消旋体,如分步结晶、蒸馏和/或色谱法。
对映体混合物,例如,用同样方法可以获得的外消旋体可以用已知方法折分成旋光对映体,如从光学活性溶剂中重结晶,手性吸附剂上的色谱法,如吸附剂为乙酰纤维素的高效液相色谱(HPLC),借助适当的微生物,用特殊的固定化酶裂解,形成包夹物,如用只络合一种对映体的手性冠醚,或转化成非对映体的盐,如用碱性消旋体终产物与光学活性酸反应,如羧酸,例如樟脑酸,酒石酸或苹果酸,如樟脑磺酸,分离用所述方式可获得的非对映体混合物,如根据溶解度的不同使用分步结晶得到非对映体,再通过适当的试剂如碱性试剂的作用从中释放出想要的对映体。
根据本发明不仅可以通过分离合适的异构体混合物,还可以通过公知的非对映体选择性或对映体选择性合成的方法,如采用具有合适的立体化学的起始原料来实施本发明方法,从而获得纯非对映体或对映体。
如果单独成分具有不同的生物活性,在所有情况下分离或合成更具活性的异构体是有利的,如对映体或非对映体,或异构体混合物,如对映体混合物或非对映体混合物,
式I化合物和,如果合适的话,其互变异构体,可以也以水合物的形式获得和/或包含其它溶剂(如果合适的话),如以固体形式存在的已经用于化合物结晶的那些溶剂。
已经发现本发明的式I化合物具有非常有利的保护有用植物免受植物病源微生物,如真菌、细菌或病毒导致的病害的活性谱。
本发明涉及一种控制或预防有用植物不被植物病源微生物侵染的方法,其中包括将式I化合物作为有效成分施用于植物,植物部分或其所在地。本发明式I化合物的特征在于在低施用水平下具有极好的活性,良好的植物耐受性和环境安全性。它们具有有用的治疗性、预防性和系统性质,可以用于保护许多有用植物。式I化合物可以用于抑制或破坏发生在植物上或不同有用植物的植物部分(果实,花,叶,茎,块茎,根)上的病害,并且同时还保护后期生长的那些植物部分不受如植物病源微生物的侵染。
还可以将式I化合物用作种子拌种剂来处理植物繁殖材料,尤其是种子(果实,块茎,谷粒)和植物插条(如稻),来保护它们不受真菌和发生在土壤中的植物病源真菌的侵染。
此外,本发明式I化合物可以用来控制相关领域的真菌,如用于保护工业材料,包括木材和木材有关的工业品,及用于食品储藏或卫生管理。
式I化合物,例如,对以下种类的病源真菌有效:半知菌(如葡萄孢属,梨孢菌属,长蠕孢属,镰刀属,壳针孢属,尾孢属和链格孢属)和担子菌(如丝核菌属,驼孢锈菌属,柄锈菌属(Puccinia))。另外,它们还对子囊菌纲有效(如黑星菌属和白粉菌属,叉丝单囊壳属(Podosphaera),链核盘菌属,钩丝壳属(Uncinula))和卵菌纲(如疫霉属,腐霉,单轴霉属)。已经发现本发明式I化合物对白粉病(Erysiphe spp.)有显著的活性。另外,式I新化合物对植物病源细菌和病毒也有效(如黄单孢菌,假单胞菌,梨火疫病以及马铃薯花叶病毒)。已经发现对亚洲大豆锈病(Phakopsora pachyrhizi)有良好的活性。
在本发明范围内,典型地要保护的有用植物包括下述植物种类:谷物(小麦,大麦,黑麦,燕麦,稻,玉米,高梁及相关种类);甜菜(糖用甜菜和饲料甜菜);梨果,核果和浆果(苹果,梨,李子,桃,扁桃,樱桃,草莓,木莓和黑莓);豆科植物(菜豆,小扁豆,豌豆,大豆);油类植物(油菜,芥菜,罂粟,橄榄,向日葵,椰子,蓖麻,可可豆,落花生);黄瓜属植物(南瓜,黄瓜,甜瓜);纤维植物(棉花,亚麻,大麻,黄麻);柑橘类水果(桔子,柠檬,柚子,中国柑橘);蔬菜(菠菜,莴苣,芦笋,甘蓝,胡萝卜,洋葱,番茄,马铃薯,青椒);樟科植物(鳄梨,肉桂,樟脑)或植物如烟草,坚果,咖啡,茄子,甘蔗,茶叶,胡椒,葡萄,啤酒花,香蕉和天然橡胶植物,以及观赏植物。
术语″作物″应理解为还包括由于常规育种方法或基因工程方法使其耐受除草剂如溴苯腈或多类除草剂(如HPPD抑制剂,ALS抑制剂,例如氟嘧磺隆、氟磺隆和三氟啶磺隆,EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸合成酶)抑制剂,GS(谷氨酰胺合成酶)抑制剂)的作物。已通过常规育种方法(突变形成)使其耐咪唑啉酮类如甲氧咪草烟的作物的实例是Clearfield夏季芸苔(Canola)。通过基因工程方法使之耐除草剂或除草剂类的作物的实例包括抗草甘膦和抗草铵膦的玉米,该品种可根据商品名RoundupReady,HerculexI和LibertyLink从市场上买到。
术语″作物″应理解为还包括已通过使用重组DNA技术转化使其能合成一种或多种选择性作用毒素的作物,所述毒素如已知来自于毒素产生细菌,特别是芽孢杆菌属的那些细菌。
可通过所述转基因植物表达的毒素包括,例如杀虫蛋白质,例如来自于枯草芽孢杆菌或日本甲虫芽孢杆菌的杀虫蛋白质;或来自于苏云金芽孢杆菌的杀虫蛋白质,如δ-内毒素,例如CryIA(b),CryIA(c),CryIF,CryIF(a2),CryIIA(b),CryIIIA,CryIIIB(b1)或Cry9c,或植物杀虫蛋白质(VIP),例如VIP1、VIP2、VIP3或VIP3A;或细菌共生线虫的杀虫蛋白质,例如光杆状菌属或致病杆菌属,如发光光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素;植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、HMG-COA-还原酶,离子通道阻断剂,如钠通道或钙通道阻断剂,保幼激素酯酶,利尿激素受体、二苯乙烯合成酶、联苄合成酶、几丁酶和葡聚糖酶。
在本发明范围内,δ-内毒素例如CryIA(b),CryIA(c),CryIF,CryIF(a2),CryIIA(b),CryIIIA,CryIIIB(b1)或Cry9c,或植物杀虫蛋白(VIP),例如VIP1,VIP2,VIP3或VIP3A应理解为显然还包括混合毒素、截短(truncated)毒素和改性毒素。混合毒素是通过那些蛋白质的不同功能区的新组合重组产生的(见,例如WO02/15701)。截短毒素例如截短的CryIA(b)是已知的。就改性毒素来说,天然存在的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如在CryIIIA055的情况下,一种组织蛋白酶-D-识别序列被插入CryIIIA毒素(见WO03/018810)。
上述毒素或能合成上述毒素的转基因植物的实例公开于例如EP-A-0374753,WO93/07278,WO95/34656,EP-A-0427529,EP-A-451878和WO03/052073。
上述转基因植物的制备方法是本领域技术人员通常已知的,描述于例如上述出版物中。CryI-型脱氧核糖核酸及其制备已知于例如WO95/34656,EP-A-0367474,EP-A-0401979和WO90/13651。
转基因植物中所含毒素使得植物对有害昆虫有耐受性。所述昆虫可以存在于任何昆虫分类群,但尤其是通常在甲虫(鞘翅目)、双翅昆虫(双翅目)和蝴蝶(鳞翅目)中发现的。
含有一个或多个编码杀虫剂抗性和表达一种或多种毒素的基因的转基因植物是已知的,其中一些是市场上可买到的。所述植物的实例是:YieldGard(玉米品种,表达CryIA(b)毒素);YieldGard Rootworm(玉米品种,表达CryIIIB(b1)毒素);YieldGard Plus(玉米品种,表达CryIA(b)和CryIIIB(b1)毒素);Starlink(玉米品种,表达Cry9(c)毒素);Herculex I(玉米品种,表达CryIF(a2)毒素和获得对除草剂草铵膦铵盐耐药性的酶phosphinothricineN-乙酰基转移酶(PAT));NuCOTN33B(棉花品种,表达CryIA(c)毒素);Bollgard I(棉花品种,表达CryIA(c)毒素);Bollgard II(棉花品种,表达CryIA(c)和CryIIA(b)毒素);VIPCOT(棉花品种,表达VIP毒素);NewLeaf(马铃薯品种,表达CryIIIA毒素);NatureGard)和Protecta。
所述转基因作物的其他实例是:
1.Btll玉米,来自Syngenta Seeds SAS,Chemin de 1′Hobit27,F-31 790 St.Sauveur,法国,登记号C/FR/96/05/10。遗传改性的玉蜀黍,通过转基因表达截短的CryIA(b)毒素,使之能抵抗欧洲玉米螟(Ostrinia nubilalis和Sesamia nonagrioides)的侵袭。Bt11玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,来自Syngenta Seeds SAS,Cheminde 1′Hobit27,F-31790St.Sauveur,France,登记号C/FR/96/05/10。遗传改性的玉蜀黍,通过转基因表达CryIA(b)毒素使之能抵抗欧洲玉米螟(Ostrinia nubilalis and Sesamia nonagrioides)的侵袭。Bt176玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
3.MIR604玉米,来自Syngenta Seeds SAS,Chemin de 1′Hobit27,F-31790St.Sauveur,法国,登记号C/FR/96/05/10。通过转基因表达改性的CryIIIA毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-D-蛋白酶识别序列而改性的Cry3A055。所述转基因玉米的制备描述于WO03/018810。
4.MON863玉米,来自Monsanto Europe S.A.270-272Avenue deTervuren,B-1150 Brussels,比利时,登记号C/DE/02/9。MON863表达CryIIIB(b1)毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC531棉花,来自Monsanto Europe S.A.270-272 Avenue deTervuren,B-1150 Brussels,比利时,登记号C/ES/96/02。
6.1507玉米,来自Pioneer Overseas Corporation,AvenueTedesco,7B-1160Brussels,比利时,登记号C/NL/00/10。遗传改性的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性和PAT蛋白质以获得对除草剂草铵膦铵盐的耐受性。
7.NK603×MON810玉米,来自Monsanto Europe S.A.270-272Avenue de Tervuren,B-1150Brussels,比利时,登记号C/GB/02/M3/03。通过遗传改性的品种NK603和MON810杂交,由常规育种的杂交玉米品种构成。NK603×MON810玉米转基因表达由土壤杆菌属菌株CP4获得的CP4EPSPS蛋白质,使之耐除草剂Roundup(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的CryIA(b)毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
昆虫抗性植物的转基因作物还描述于BATS(Zentrum fürBiosicherheit und Nachhaltigkeit,Zentrum BATS,Clarastrasse13,4058Basel,Switzerland)Report2003,(http://bats.ch)。
术语“作物”应理解为还包括通过使用重组DNA技术转化使之能合成具有选择性作用的抗病原物质例如所谓的″致病相关蛋白″(PRPs,见例如EP-A-0392225)的作物。所述抗病原物质和能合成所述抗病原物质的转基因植物的实例已知于例如EP-A-0392225、WO95/33818和EP-A-0353191。所述转基因植物的制造方法是本领域技术人员通常已知的,并且描述于例如上述出版物中。
能被所述转基因植物表达的抗病原物质包括例如离子通道阻断剂,如钠和钙通道的阻断剂,例如病毒性KP1,KP4或KP6毒素;二苯乙烯合成酶;联苄合成酶;几丁酶;葡聚糖酶;所谓的″致病相关蛋白″(PRPs;见例如EP-A-0392225);由微生物产生的抗病原物质例如肽抗生素或杂环抗生素(见例如WO95/33818)或植物病原体防御中涉及的蛋白或多肽因子(所谓的″植物病害抗性基因″,如WO03/0009O6所述)。
本发明中使用的术语有用植物的“所在地”意欲包括所述有用植物的生长地,所述有用植物的繁殖材料的播种地或植物繁殖材料将要被种植的土壤。所述所在地的实例如作物生长的农田。
术语“植物繁殖材料”应该被理解为表示植物的再生部分,如可以用作繁殖后者的种子,和营养材料,如插条或块茎,如马铃薯。可以提及例如种子(严格意义上的),根,果实,块茎,鳞茎,球茎和植物部分。发芽植物和萌芽后或从土壤中发芽后将被移植的植物幼苗。这些植物幼苗可以在移植之前进行完全或部分浸渍处理。优选“植物繁殖材料”理解为表示种子。
式I化合物可以以未改变的形式或,优选,与制剂领域中常规使用的载体和助剂一起使用。
因此,本发明还涉及控制和保护植物病源微生物的组合物,包括式I化合物和惰性载体,和一种控制或预防病源微生物侵染有用植物的方法,其中将包括作为活性成分的式I化合物和载体的组合物施用于植物,植物部分或其所在地。
为此,式I化合物和惰性载体可以用已知方法常规制剂成乳油,可涂覆糊剂,直接喷洒或稀释的溶液,稀释乳剂,可湿性粉剂,可溶性粉剂,粉剂,粒剂,还有胶囊剂如在聚合物中。根据组合物的类型,相应于作用对象和流行环境来选择施用方法,如喷雾,弥雾,撒粉,散洒,涂覆或浇泼。组合物还可以包含其它助剂如稳定剂,消泡剂,粘度调节剂,黏合剂或胶粘剂和肥料,微量营养素供体或其它药剂以获得特殊作用。
合适的载体和助剂可以是固体或液体,是制剂技术中有用的物质,如天然或再生矿物质,溶剂,分散剂,湿润剂,胶粘剂,增稠剂,黏合剂或肥料。所述载体的实例描述于WO97/33890。
式I化合物或包含一种式I化合物作为有效成分和惰性载体的组合物,可以与其它化合物同时或依次施用于作物所在地或将被处理的作物所在地。这些化合物可以是如肥料或微量营养素供体或其它影响植物生长的制剂。它们还可以是选择性除草剂和杀虫剂,杀真菌剂,杀细菌剂,杀线虫剂,软体动物杀灭剂或几种这些制剂的混合物,如果需要的话,可以与制剂领域中常规的其它载体,表面活性剂或施用促进助剂一起施用。
施用式I化合物或包含式I化合物作为有效成分和惰性载体的组合物的优选方法是叶面施用。施用的频率和比率依据被相应病源体侵染的风险率。然而,式I化合物还可以以液体剂型浇注植物所在地,通过土壤(内吸作用)通过根部渗入整个植株,或将化合物以固体形式施用于土壤,如粒剂(土施)。对于水稻可以将所述粒剂施用于灌水的稻田。式I化合物还可以以液体杀真菌剂或者固体制剂涂覆形式通过种子浸渍施用于种子(涂覆)或块茎。
制剂,即,包含式I化合物和,需要的话,固体或液体助剂,以已知方式制备,典型地通过直接混合和/或与增量剂如溶剂,固体载体和,可选的,表面活性化合物(表面活性剂)一起研磨。
农药制剂通常包含按重量计0.1-99%,优选0.1-95%的式I化合物,99.9-1%,优选99.8-5%的固体或液体助剂,和0-25%,优选0.1-25%的表面活性剂。
商业产品优选加工成浓缩物,最终用户通常施用稀释制剂。
有利的施用比率通常为5g-2kg活性成分(a.i.)/公顷(ha),优选10g-1kga.i./ha,最优选20g-600ga.i./ha。当被用作拌种剂时,常规施用比率是10mg-1g活性物质/kg种子。对于想要的作用的施用比率可以通过试验来确定。这依作用类型,有用植物的生长阶段,和施用条件(场所,时机,施用方法)而定,并且可以,依据这些参数,在宽范围内变化。
令人惊奇的是,已经发现式I化合物还可以用于保护有用作物不受病源微生物的侵染以及治疗被病源微生物侵染的有用作物方法,其中包括结合草甘膦与至少一种式I化合物施用于植物或其所在地,其中所述作物对草甘膦抗性或敏感。
与不结合草甘膦相比,所述方法意料不到地提高了病害防治效果。所述方法通过式I化合物的作用对于提高病害防治效果有效。然而草甘膦和至少一种式I化合物的混合物可以至少部分扩大由式I化合物单独作用的病害防治谱,还可以发现在草甘膦的存在下式I化合物对于已知其单独防治的病害的活性有所提高。
所述方法对于病源性微生物真菌界的担子菌亚门,担子菌纲,锈菌亚纲和锈菌目(通常指锈菌类)特别有效。对于农业有相当大的影响的锈菌包括层锈菌科,特别是层锈菌属,例如还被称作亚洲大豆锈病的豆薯层锈菌,和锈菌科,尤其是锈菌属如禾柄锈菌,也称黑锈病。
所述方法的一个实施方式是保护有用作物不受病源微生物的侵染和/或防治有用作物被病源微生物侵染的方法,所述方法包括同时施用草甘膦,包括其盐或酯,和至少一种对病源微生物有活性的式I化合物于选自植物、植物部分和植物所在地中的至少之一。
令人惊奇的是,已经发现上述式I化合物或其药用盐还对于治疗和/或预防动物的微生物感染具有有益的活性作用谱。
“动物”可以指任何动物,如昆虫,哺乳动物,爬行动物,鱼类,两栖动物,优选哺乳动物,最优选人类。“治疗”指使用在被微生物感染的动物身上,目的是减少或减缓或阻止感染的加剧或扩大,或为了减少感染或治愈感染。“预防”指使用在没有明显微生物感染症状的动物身上,目的是防止任何将来的感染,或为了减少或减缓任何将来感染的加剧或扩大。
本发明提供了式I化合物在制备用于治疗和/或预防动物的微生物感染的药物中的用途。还提供了式I化合物的药物用途。还提供了式I化合物作为一种抗微生物药物在动物治疗方面的用途。本发明还提供了一种药物组合物,包括式I化合物或其药物可接受的盐作为有效成分,和药物可接受的稀释剂或载体。所述组合物可用于治疗和/或预防动物的抗微生物感染。所述药物组合物可以制成适于口服给药的形式,如片剂,锭剂,硬胶囊剂,水悬浮剂,油悬浮剂,乳剂,分散粉剂,分散粒剂,糖浆和酏剂。可选地,所述药物组合物可以制成适于局部用药的形式,如喷雾剂、乳膏或洗液。可选地,所述药物组合物可以制成适于注射用药的形式,如注射剂。可选地,所述药物组合物可以制成适于吸入用药的形式,如胶体喷雾剂。
式I化合物对于多种能够导致动物微生物感染的微生物物种有效。这类微生物物种的实例如致曲霉病的那些如烟曲霉,黄曲霉,红曲霉,构巢曲霉和黑曲霉,致芽生菌病的如皮炎芽生菌;致念珠菌病的如白假丝酵母,光滑念珠菌,热带假丝酵母,近平滑假丝酵母,克鲁丝假丝酵母和葡萄牙假丝酵母;致球孢子菌病的如粗球孢子菌;致隐球菌病的如微荚膜新隐球酵母;致组织胞浆菌病的如荚膜组织孢浆菌和致按合菌病的如伞枝犁头霉,微小根毛霉和少根根霉。进一步的实例有镰刀霉属如尖镰孢和腐皮镰孢和足放线病菌属如尖端赛多孢子菌和多育赛多孢子菌。更进一步的实例有小孢霉属,发癣菌属,表皮癣菌属,毛霉属,Sporothorix Spp,瓶霉属,枝孢属,Petriellidium spp,孢子菌属和组织孢浆菌属。
以下非限制性实施例更详细地、非限制地阐明了上述本发明。
制备实施例:
实施例P1:制备3-(1,1-二甲基丙基)-2-甲基-苯胺:
将4,13g(17,1mmol)2-溴-3-(1,1-二甲基丙基)苯胺和7ml的98%甲酸在80℃下加热3,5小时。冷却后加入300ml水。用乙酸乙酯提取水相,及用硫酸钠干燥有机相,水喷射真空蒸发有机溶剂。在己烷中结晶纯化获得的产物。从而得到4,17g褐色固体的N-(2-溴-3-(1,1-二甲基丙基)苯基)甲酰胺(m.p.88-89℃,理论值的90%)。
将3,4g(12,6mmol)N-(2-溴-3-(1,1-二甲基丙基)苯基)甲酰胺溶解于120ml乙醚和四氢呋喃的混合物中。冷却至-78℃后,滴加9,47ml(15,16mmol)的1,6摩尔的甲基锂的Et2O溶液。在-78℃下搅拌2小时后,将溶液冷却至-100℃,并滴加10,26ml(16,42mmol)的1,6摩尔的正丁基锂的Et2O溶液。-100℃下搅拌3小时后,将混合物温热至-78℃,并滴加3,05g(21,47mmol)溶于14ml绝对四氢呋喃的甲基碘溶液。混合物在-78℃下搅拌1h后,缓慢温热至室温。将冷水加入反应混合物并用乙酸乙酯提取水相,用硫酸钠干燥后,并用水喷射真空蒸发有机溶剂,在硅胶柱色谱上纯化反应产物(流动相:己烷/乙酸乙酯2∶1)。得到1,91g无色晶体N-(2-甲基-3-(1,1-二甲基丙基)苯基)甲酰胺(m.p.51-53℃,理论值的74%)。
将2,21g(10,77mmol)N-(2-甲基-3-(1,1-二甲基丙基)苯基)甲酰胺、1,42g(21.54mmol)85%氢氧化钾和9ml甲醇在回流温度下加热搅拌15小时。冷却后加入100ml水,用乙酸乙酯提取反应混合物。在硫酸钠上干燥有机相后,水喷射真空蒸发有机溶剂,反应产物通过蒸馏纯化(bp.大约70℃,13,33Pa)。从而得到1.7g无色油状物2-甲基-3-(1,1-二甲基丙基)苯胺(理论值的89%)。
实施例P2:制备3-(1,1-二甲基丙基)-2-乙烯基-苯胺
将2,63g(8,24mmol)1-(1,1-二甲基丙基)-2-碘-3-硝基苯和3,4g(10,72mmol)三丁基乙烯基锡溶解于30ml绝对二氧杂环己烷。之后,加入0,11g(0,12mmol)三(二亚苄基丙酮)二钯(Pd2(dba)3)、0,12g(0,24mmol)二(三-叔丁基膦)合钯(Pd[P(叔丁基)3]2)和2,75g(18,14mmol)CsF。在氮气氛下,将反应混合物加热至50℃保持2小时。加入冷却冰水后,用乙酸乙酯提取所得混合物。在硫酸钠上干燥有机相后,水喷射真空蒸发有机溶剂,在硅胶柱色谱上纯化反应产物(洗脱剂:己烷/二氯甲烷5∶1)。从而得到1,75g黄色油状1-(1,1-二甲基)-2-乙烯基-3-硝基苯(理论值的97%)。
将1,75g(8,05mmol)1-(1,1-二甲基)-2-乙烯基-3-硝基苯、0,67g铁粉、7ml水、7,6ml正丙醇和2,4ml乙酸的混合物加热至85℃保持6小时。之后加入200ml水。用乙酸乙酯提取反应混合物。用盐水洗涤有机相并用硫酸钠干燥。水喷射真空蒸发溶剂后,在硅胶柱色谱上纯化反应产物(洗脱剂:环己烷/二氯甲烷2∶1)。得到0,55g浅褐色油状物3-(1,1-二甲基丙基)-2-乙烯基-苯胺(理论值的36%)。
实施例P3:制备3-叔丁基-2-乙基-苯胺
在氢化器中,将1,5g(8,55mmol)1-叔丁基-2-乙烯基-3-硝基苯和250mg5%Pd/C和20ml绝对甲醇的混合物室温下氢化2,5小时。滤除催化剂,水喷射真空蒸发溶剂。反应粗产物可以直接用于下一步化学转化。得到1,5g浅褐色液体3-叔丁基-2-乙烯基-苯胺(理论值的98%)。
实施例P4:制备3-叔丁基-2-丙-1-炔基-苯胺
将3,55g(11,65mmo1)1-叔丁基-2-碘-3-硝基苯和4,6g(13,97mmol)(三丁基丙-1-炔基)锡溶于20ml绝对二氧杂环己烷。之后加入0,16g(0,175mmol)三(二亚苄基丙酮)二钯(Pd2(dba)3)、0,18g(0,35mmol)二(三-叔丁基膦)合钯(Pd[P(叔丁基)3]2)和3,9g(25,6mmol)氟化铯(CsF)。在氮气氛下,将得到的混合物加热搅拌至50-55℃保持6小时。冷却反应混合物,加入冰水并用乙酸乙酯提取混合物。用硫酸钠干燥有机溶剂,水喷射真空蒸发溶剂后,在硅胶柱色谱上纯化反应产物(洗脱剂:己烷)。从而得到2.4g黄色液体1-叔丁基-2-丙-1-炔基-3-硝基苯(理论值的94%)。
将1,5g(6,9mmol)1-叔丁基-2-丙-1-炔基-3-硝基苯、0,6g铁粉、6ml水、6,6ml正丙醇和2ml乙酸的混合物加热至85℃保持3小时。之后加入100ml水。用乙酸乙酯提取反应混合物。用盐水洗涤有机相并用硫酸钠干燥。蒸发溶剂后,在硅胶柱色谱上纯化反应产物(洗脱剂:己烷/乙酸乙酯10∶1)。从而得到0,7g浅褐色油状3-叔丁基-2-丙-1-炔基-苯胺(理论值54%)。
实施例P5:制备1-甲基-3-三氟甲基-1H-吡唑-4-羧酸(3-叔丁基-2-乙
烯基苯基)酰胺
将197mg(1,01mmol)1-甲基-3-三氟甲基-1H-吡唑-4-羧酸和135mg(1,07mmol)草酰氯溶于8ml二氯甲烷。将溶液在催化量二甲基甲酰胺(DMF)的存在下室温搅拌3小时。之后,将该溶液缓慢加入由180mg(1,01mmol)3-叔丁基-2-乙烯基-苯胺、155mg(1,52mmol)三乙胺和7ml二氯甲烷组成的溶液中。然后将得到的反应混合物在室温下搅拌16小时。水喷射真空除去溶剂后,用硅胶快速分离色谱(洗脱剂:己烷/乙酸乙酯2∶1)纯化残余物。得到0,27g无色固体1-甲基-3-三氟甲基-1H-吡唑-4-羧酸(3-叔丁基-2-乙烯基苯基)酰胺(m.p.118-119℃;理论值的76%)。
优选的式I化合物如下表所列。
表1:式IA化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>11</sub> | R<sub>12</sub> | R<sub>13</sub> |
1.1 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.6 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.11 | CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.12 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.13 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.14 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.15 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.16 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.17 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.18 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.19 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.20 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.21 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.22 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.23 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.24 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.25 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.26 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.27 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.28 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.29 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.30 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.31 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.32 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.33 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.34 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.35 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>11</sub> | R<sub>12</sub> | R<sub>13</sub> |
1.36 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.37 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.38 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.39 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.40 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.41 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.42 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.43 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.44 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.45 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.46 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.47 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.48 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.49 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.50 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.51 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.52 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.53 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CE<sub>2</sub>H | CH<sub>3</sub> | H |
1.54 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.55 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.56 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.57 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.58 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.59 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.60 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.61 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.62 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.63 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.64 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.65 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.66 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.67 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.68 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.69 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.70 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.71 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>11</sub> | R<sub>12</sub> | R<sub>13</sub> |
1.72 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.73 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.74 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.75 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.76 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.77 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.78 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.79 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.80 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.81 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.82 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.83 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.84 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.85 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.86 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.87 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.88 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.89 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.90 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.91 | C≡CH | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.92 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.93 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.94 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.95 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.96 | C≡CH | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.97 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.98 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.99 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.100 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.101 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.102 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.103 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.104 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.105 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.106 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.107 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>11</sub> | R<sub>12</sub> | R<sub>13</sub> |
1.108 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.109 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.110 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.111 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.112 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.113 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.114 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.115 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
1.116 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.117 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.118 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.119 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.120 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
1.121 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.122 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.123 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.124 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.125 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
1.126 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.127 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.128 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.129 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.130 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
1.131 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.132 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.133 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.134 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
1.135 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
表2:式IB化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>21</sub> | R<sub>22</sub> | R<sub>23</sub> |
2.1 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.6 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.11 | CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.12 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.13 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.14 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.15 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.16 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.17 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.18 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.19 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.20 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.21 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.22 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.23 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.24 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.25 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.26 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.27 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.28 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.29 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.30 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.31 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.32 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.33 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.34 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.35 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.36 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>21</sub> | R<sub>22</sub> | R<sub>23</sub> |
2.37 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.38 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.39 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.40 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.41 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.42 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.43 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.44 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.45 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.46 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.47 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.48 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.49 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.50 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.51 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.52 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.53 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.54 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.55 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.56 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.57 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.58 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.59 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.60 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.61 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.62 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.63 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.64 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.65 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.66 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.67 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.68 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.69 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.70 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.71 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.72 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>21</sub> | R<sub>22</sub> | R<sub>23</sub> |
2.73 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.74 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.75 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.76 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.77 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.78 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.79 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.80 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.81 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.82 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.83 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.84 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.85 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.86 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.87 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.88 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.89 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.90 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.91 | C≡CH | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.92 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.93 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.94 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.95 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.96 | C≡CH | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.97 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.98 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.99 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.100 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.101 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.102 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.103 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.104 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.105 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.106 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.107 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.108 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>21</sub> | R<sub>22</sub> | R<sub>23</sub> |
2.109 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.110 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.111 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.112 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.113 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.114 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.115 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> | H |
2.116 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.117 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.118 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.119 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.120 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> | H |
2.121 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.122 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.123 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.124 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.125 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> | H |
2.126 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.127 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.128 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.129 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.130 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | H |
2.131 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.132 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.133 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.134 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
2.135 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | F |
表3:式IC化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>31</sub> | R<sub>32</sub> |
3.1 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.6 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.11 | CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.12 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.13 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.14 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.15 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.16 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.17 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.18 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.19 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.20 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.21 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.22 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.23 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.24 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.25 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.26 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.27 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.28 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.29 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.30 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>31</sub> | R<sub>32</sub> |
3.31 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.32 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.33 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.34 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.35 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.36 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.37 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.38 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.39 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.40 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.41 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.42 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.43 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.44 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.45 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.46 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.47 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.48 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.49 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.50 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.51 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.52 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.53 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.54 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.55 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.56 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.57 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.58 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.59 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.60 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.61 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.62 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.63 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.64 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.65 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.66 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>31</sub> | R<sub>32</sub> |
3.67 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.68 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.69 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.70 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.71 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.72 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.73 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.74 | C≡CH | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.75 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.76 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.77 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.7 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.79 | C≡CH | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.80 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.81 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.82 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.83 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.84 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.85 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.86 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.87 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.88 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.89 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.90 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.91 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.92 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.93 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
3.94 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.95 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.96 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.97 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.98 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
3.99 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.100 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.101 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.102 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>2</sub>H | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>31</sub> | R<sub>32</sub> |
3.103 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CFH<sub>2</sub> | CH<sub>3</sub> |
3.104 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.105 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.106 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.107 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
3.108 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
表4:式ID化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>41</sub> | R<sub>42</sub> |
4.1 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.6 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.11 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.12 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.13 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.14 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.15 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.16 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.17 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.18 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.19 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.20 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>41</sub> | R<sub>42</sub> |
4.21 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.22 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.23 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.24 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.25 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.26 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.27 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.28 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.29 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.30 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.31 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.32 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.33 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.34 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.35 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.36 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.37 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.38 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.39 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.40 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.41 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.42 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.43 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.44 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.45 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.46 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.47 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.48 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.49 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.50 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.51 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.52 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.53 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.54 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.55 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.56 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>41</sub> | R<sub>42</sub> |
4.57 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.58 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.59 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.60 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.61 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.62 | C≡CH | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.63 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.64 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.65 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.66 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.67 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.68 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.69 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.70 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.71 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> | CH<sub>3</sub> |
4.72 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.73 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.74 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.75 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.76 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
4.77 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.78 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.79 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.80 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
4.81 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
表5:式IE化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>51</sub> |
5.1 | CH<sub>3</sub> | CH<sub>3</sub> | Cl |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>51</sub> |
5.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Cl |
5.6 | CH<sub>3</sub> | CH<sub>3</sub> | Br |
5.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Br |
5.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Br |
5.11 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
5.12 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.13 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.14 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.15 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
5.16 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | Cl |
5.17 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.18 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.19 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.20 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Cl |
5.21 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | Br |
5.22 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Br |
5.23 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.24 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.25 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Br |
5.26 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
5.27 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.28 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.29 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.30 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
5.31 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | Cl |
5.32 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.33 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | Br |
5.34 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Br |
5.35 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
5.36 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.37 | CH=CH<sub>2</sub> | CH<sub>3</sub> | Cl |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>51</sub> |
5.38 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.39 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.40 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.41 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Cl |
5.42 | CH=CH<sub>2</sub> | CH<sub>3</sub> | Br |
5.43 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | Br |
5.44 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.45 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.46 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Br |
5.47 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
5.48 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.49 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.50 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.51 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
5.52 | C≡CH | CH<sub>3</sub> | Cl |
5.53 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.54 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.55 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.56 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Cl |
5.57 | C≡CH | CH<sub>3</sub> | Br |
5.58 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | Br |
5.59 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.60 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.61 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Br |
5.62 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> |
5.63 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.64 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.65 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.66 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
5.67 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | Cl |
5.68 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Cl |
5.69 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.70 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Cl |
5.71 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Cl |
5.72 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | Br |
5.73 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | Br |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>51</sub> |
5.74 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.75 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | Br |
5.76 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | Br |
5.77 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
5.78 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
5.79 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.80 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
5.81 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
表6:式IF化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>61</sub> |
6.1 | CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
6.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
6.6 | CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
6.7 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.8 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.9 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.10 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> |
6.11 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
6.12 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.13 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.14 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.15 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
6.16 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
6.17 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.18 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.19 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.20 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> |
化合物编号 | R<sub>1</sub> | R<sub>2</sub> | R<sub>61</sub> |
6.21 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
6.22 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.23 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
6.24 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.25 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
6.26 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.27 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.28 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.29 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
6.30 | CH=CH<sub>2</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
6.31 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.32 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.33 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.34 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> |
6.35 | C≡CH | CH<sub>3</sub> | CF<sub>3</sub> |
6.36 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.37 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.38 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.39 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
6.40 | C≡CH | CH<sub>3</sub> | CH<sub>3</sub> |
6.41 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.42 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.43 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.44 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> |
6.45 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CF<sub>3</sub> |
6.46 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CF<sub>3</sub> |
6.47 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.48 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CF<sub>3</sub> |
6.49 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CF<sub>3</sub> |
6.50 | C≡CCH<sub>3</sub> | CH<sub>3</sub> | CH<sub>3</sub> |
6.51 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
6.52 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.53 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> | CH<sub>3</sub> |
6.54 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> | CH<sub>3</sub> |
表Z1:式II中间体化合物
化合物编号 | R<sub>1</sub> | R<sub>2</sub> |
Z1.1 | CH<sub>3</sub> | CH<sub>3</sub> |
Z1.2 | CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.3 | CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.4 | CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.5 | CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
Z1.6 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
Z1.7 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.8 | CH<sub>2</sub>CH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.9 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.10 | CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
Z1.11 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>3</sub> |
Z1.12 | CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.13 | CH=CH<sub>2</sub> | CH<sub>3</sub> |
Z1.14 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.15 | CH=CH<sub>2</sub> | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.16 | CH=CH<sub>2</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.17 | CH=CH<sub>2</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
Z1.18 | CH=CHCH<sub>3</sub> | CH<sub>3</sub> |
Z1.19 | CH=CHCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.20 | CH=CHCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.21 | CH=CHCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.22 | CH=CHCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
Z1.23 | C≡CH | CH<sub>3</sub> |
Z1.24 | C≡CH | CH<sub>2</sub>CH<sub>3</sub> |
Z1.25 | C≡CH | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.26 | C≡CH | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.27 | C≡CH | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
Z1.28 | C≡CCH<sub>3</sub> | CH<sub>3</sub> |
Z1.29 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH<sub>3</sub> |
Z1.30 | C≡CCH<sub>3</sub> | CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.31 | C≡CCH<sub>3</sub> | CH<sub>2</sub>CH(CH<sub>3</sub>)<sub>2</sub> |
Z1.32 | C≡CCH<sub>3</sub> | CH<sub>2</sub>C(CH<sub>3</sub>)<sub>3</sub> |
物理数据(熔点℃):
本说明书中,温度以摄氏计;“NMR”指核磁共振波谱;MS表示质谱;以及除非相应的浓度以其它单位标示,“%”表示重量百分比,。以下缩写通用于本说明书:
m.p.=熔点 b.p.=沸点
S=单峰 br=宽度
d=双峰 dd=双二重峰
t=三重峰 q=四重峰
m=多重峰 ppm=百万分之一
表7显示了所选择的表1-6中Z1化合物的熔点和NMR数据,都是以CDCl3为溶剂(除非另有提及;如果混合溶剂存在,表示为,例如(CDCl3/d6-DMSO)),(未尝试列出所有情况下的所有特征数据)。
表8:
化合物编号 | 1H-NMR数据:(ppm/多重度/H数目). | m.p./(℃) |
1.1 | 树脂状物 | |
1.2 | 147-150 | |
1.6 | 蜡状物 | |
1.7 | 123-126 | |
1.26 | 187-187 | |
1.27 | 158-159 | |
1.31 | 162-164 | |
1.32 | 115-116 | |
1.51 | 176-177 | |
1.53 | 149-150 | |
1.61 | 118-119 | |
1.62 | 95-96 | |
1.66 | 114-115 | |
1.67 | 93-96 | |
1.111 | 85-87 | |
1.116 | 101-103 |
2.1 | 180-185 | |
2.2 | 185-188 | |
2.26 | 134-134 | |
2.27 | 160-163 |
2.51 | 167-168 | |
2.62 | 树脂状物 | |
2.66 | 蜡状物 | |
2.111 | 59-61 | |
3.1 | 树脂状物 | |
4.1 | 146-147 | |
4.2 | 90-92 | |
4.16 | 179-181 | |
4.17 | 128-130 | |
4.31 | 166-168 | |
4.37 | 139-140 | |
4.67 | 90-91 | |
5.1 | 116-117 | |
5.16 | 137-138 | |
5.17 | 127-128 | |
5.31 | 163-164 | |
5.37 | 126-127 | |
5.67 | 84-86 | |
6.6 | 树脂状物 | |
Z1.1 | 1.41(s,9H),2.39(s,3H),3.57(s(宽峰),2H),6.61(d,1H),6.85(d,1H),6.98(tr,1H) | 油状物 |
Z1.2 | 0.69(tr,3H),1.37(s,6H),1.81(q,2H),2.26(s,3H),3.55(s(宽峰),2H),6.61(d,1H),6.79(d,1H),6.96(tr,1H) | 油状物 |
Z1.6 | 1.20(tr,3H),1.41(s,9H),2.84(q,2H),3.64(s(宽峰).2H),6.59(d,1H),6.85(dd,1H),6.97(tr,1H) | 油状物 |
Z1.7 | 0.70(tr,3H),1.18(tr,3H),1.37(s,6H),1.78(q,2H),3.62(s(宽峰),2H),6.60(dd,1H),6.78(dd.1H),6.95(tr,1H) | 油状物 |
Z1.11 | 1.06(tr,3H),1.40(s,9H),1.60(m,2H),2.71(m,2H),3.63(s(宽峰),2H),6.60(dd,1H),6.85(dd,1H),6.96(tr,1H) | 油状物 |
Z1.13 | 1.37(s,9H),3.85(s(宽峰),2H),5.36(dd,1H),5.64(dd,1H),6.62(dd,1H),6.8-7.05(m,3H) | 油状物 |
Z1.14 | 0.65(tr,3H),1.32(s,6H),1.75(q,2H),3.83(s(宽峰),2H),5.33(dd,1H),5.90(dd,1H),6.60(d,1H),6.75(dd,1H),6.80(m,1H),7.00(tr,1H) | 油状物 |
Z1.28 | 1.47(s,9H),2.16(s,3H),4.27(s(宽峰),2H),6.59(dd,1H),6.73(dd,1H),7.00(tr,1H) | 油状物 |
Z1.29 | 油状物 |
式I化合物的剂型实施例:
实施例F-1.1至F-1.3:乳油
成分 | F-1.1 | F-1.2 | F-1.3 |
表1-6化合物十二烷基苯磺酸钙蓖麻油聚乙二醇醚(36摩尔氧乙烯单元)三丁基酚聚乙二醇醚(30摩尔氧乙烯单元)环己酮混合二甲苯 | 25%5%5%--65% | 40%8%-12%15%25% | 50%6%-4%20%20% |
任意需要浓度的乳剂可以通过水稀释所述乳油来制备。
实施例F-2:乳油
成分 | F-2 |
表1-6化合物辛基酚聚乙二醇醚(4-5摩尔氧乙烯单元)十二烷基苯磺酸钙蓖麻油聚乙二醇醚 | 10%3%3% |
(36摩尔氧乙烯单元)环己酮混合二甲苯 | 4%30%50% |
任意需要浓度的乳剂可以通过水稀释所述乳油来制备。
实施例F-3.1至F-3.4:溶液
成分 | F-3.1 | F-3.2 | F-3.3 | F-3.4 |
表1-6化合物丙二醇单甲醚聚乙二醇(相对分子量:400原子质量单位)N-甲基吡咯烷-2-酮氧化椰子油汽油(沸程:160-190°) | 80%20%---- | 10%-70%20%-- | 5%---1%94% | 95%---5%- |
溶液适于以滴剂形式使用。
实施例F-4.1至F-4.4:粒剂
成分 | F-4.1 | F-4.2 | F-4.3 | F-4.4 |
表1-6化合物高岭土高分散硅酸硅镁土 | 5%94%1%- | 10%--90% | 8%79%13%- | 21%54%7%18% |
将新化合物溶于二氯甲烷中,把溶液喷洒到载体上,然后真空蒸除溶剂。
实施例F-5.1和F-5.2:粉剂
成分 | F-5.1 | F-5.2 |
表1-6化合物 | 2% | 5% |
高分散硅酸滑石高岭土 | 1%97%- | 5%-90% |
即用粉剂通过紧密混合所有成分获得。
实施例F-6.1至F-6.3:可湿性粉剂
成分 | F-6.1 | F-6.2 | F-6.3 |
表1-6化合物木质素磺酸钠十二烷基硫酸钠二异丁基萘磺酸钠辛基酚聚乙二醇醚(7-8摩尔氧乙烯单元)高分散硅酸高岭土 | 25%5%3%--5%62% | 50%5%-6%2%10%27% | 75%-5%10%-10%- |
混合所有成分,将该混合物在合适的研磨机中充分研磨得到用水稀释即可获得任意需要浓度悬浮液的可湿性粉剂。
实施例F7:种子处理流动浓缩剂(Flowable concentrate)
表1-6化合物 40%
丙二醇 5%
丁醇共聚物PO/EO 2%
包含10-20摩尔EO的三苯乙烯苯酚 2%
1,2-苯并异噻唑啉-3-酮(20%水溶液) 0.5%
单偶氮颜料钙盐 5%
硅油(75%水乳液) 0.2%
水 45.3%
将精细研磨的活性成分与助剂紧密混合,得到悬浮浓缩物,其可以用水稀释以得到任意需要的稀释度悬浮液。通过喷雾、浇泼或浸渍可以治疗和保护活性植物及植物繁殖材料来对抗微生物侵染。
生物实施例:杀真菌作用
实施例B-1:对大冰草隐匿柄锈菌/小麦(Brownrust on wheat)的
活性
在喷雾室中用制剂化的试验化合物(0.02%活性成分)处理一周龄的小麦植株栽培品种Arina。施药1天后,通过向试验植株喷洒孢子悬浮液(1×105夏孢子/ml)来给小麦植株接种。在20℃和95%r.h.下,经过2天的培养期,将植株置于20℃和60%r.h.的温室中8天。接种10天后评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-2:对白叉丝单囊壳/苹果(苹果白粉病)的活性
在喷雾室中,用制剂化的试验化合物(0.002%活性成分)处理5周龄的苹果树苗栽培品种McIntosh。施药1天后,通过在试验植物上方摇动感染苹果白粉病的植株来将苹果植株接种。在12天22℃和60%r.h.,14/10小时(光/暗)光照管理的培养期后,评价病害发生率。
表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-3:对苹果黑星病/苹果(苹果疮痂病)的活性
在喷雾室中用制剂化的试验化合物(0.02%活性成分)处理4周龄的苹果树苗栽培品种McIntosh。施药1天后,通过向试验植株喷洒孢子悬浮液(4×105分生孢子/ml)来接种苹果植株。经过4天21℃和95%r.h.的培养期,将植株置于21℃和60%r.h.的温室中4天。再经过4天21℃和95%r.h.的培养期,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-4:对禾白粉菌/大麦(大麦白粉病)的活性
在喷雾室中,用制剂化的试验化合物(0.02%活性成分)处理1周龄的大麦植株栽培品种Express。施药1天后,通过在试验植物上方摇动感染大麦白粉病的植株来将其接种。在温室中经过6天20℃/18℃(昼/夜)和60%r.h.的培养期后,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-5:对灰葡萄孢/苹果(苹果灰霉病)的活性
在每个苹果果实栽培品种Golden Delicious上挖3个洞,每个洞滴加30μl的制剂化的试验化合物(0.002%活性成分)。施药2小时后,用移液管在每个施药点上滴加50μl的B.cinerea孢子悬浮液(4×105分生孢子/ml)。经过7天在生长室内22℃的培养期,评价病害发生率。
表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-6:对灰葡萄孢/葡萄(葡萄灰霉病)的活性
在喷雾室中用制剂化的试验化合物(0.002%活性成分)处理5周龄的葡萄树苗栽培品种Gutedel。施药2天后,通过向试验植株喷洒孢子悬浮液(1×106分生孢子/ml)来接种葡萄植株。经过4天21℃和95%r.h.的温室培养期,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-7:对灰葡萄孢/番茄(Botrytis on tomatoes)的活性
在喷雾室中,用制剂化的试验化合物(0.002%活性成分)处理4周龄的番茄植株栽培品种Roter Gnom。施药2天后,通过向试验植株喷洒孢子悬浮液(1×105分生孢子/ml)来接种番茄植株。经过4天20℃和95%r.h.的生长室培养期,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-8:对大麦网斑病菌/大麦(Net blotch on barley)的活
性
在喷雾室中,用制剂化的试验化合物(0.002%活性成分)处理1周龄的大麦植株栽培品种Express。施药2天后,通过向试验植株喷洒孢子悬浮液(3×104分生孢子/ml)来接种大麦植株。经过2天20℃和95%r.h.的培养期,将大麦植株置于20℃和60%r.h.的温室培养2天。接种4天后评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-9:对小麦壳针孢/小麦(Septoria leaf spot on wheat)
的活性
在喷雾室中用制剂化的试验化合物(0.2%活性成分)处理2周龄的小麦植株栽培品种Riband。施药1天后,通过向试验植株喷洒孢子悬浮液(10×105分生孢子/ml)来接种小麦植株。经过1天23℃和95%r.h.的培养期,将小麦植株置于23℃和60%r.h.的温室培养16天。接种18天后评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-10:对葡萄钩丝壳/葡萄(葡萄白粉病)的活性
在喷雾室中,用制剂化的试验化合物(0.02%活性成分)处理1周龄的葡萄树苗栽培品种Gutedel。施药1天后,通过在试验植物上方摇动感染葡萄白粉病的植株来将其接种。在26℃和60%r.h.的温室中经过7天的14/10小时(昼/夜)光照管理培养期后,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-11:对茄早疫病/番茄(茄早疫病)的活性
在喷雾室中,用制剂化的试验化合物(0.02%活性成分)处理4周龄的番茄植株栽培品种Roter Gnom。施药2天后,通过向试验植株喷洒孢子悬浮液(2×105分生孢子/ml)来接种番茄植株。经过3天20℃和95%r.h.的生长室培养期,评价病害发生率。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
实施例B-12:对裸黑粉菌/大麦的活性
将含有活性成分的悬浮浓缩物通过种子处理施用于感染U.nuda的冬大麦种子之后,将种子种入用农田土填充的托盘中。将托盘移至生长室中20℃保持2天,之后在2℃下保持2个星期。然后将试验移至15℃的温室,每天提供14hr光照直至开花。病害发生率以感染头数计。表1-6化合物在该试验中表现出良好的活性(<20%侵染率)。
Claims (4)
2.一种控制或预防有用植物被病源微生物侵染的方法,其中包括将权利要求1所述的式I化合物或包含该化合物为活性成分的组合物施用于植物、植物部分或其所在地。
3.一种防治和保护植物对抗植物病源微生物的组合物,包含权利要求1所述的式I化合物和惰性载体。
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US3393202A (en) * | 1965-04-26 | 1968-07-16 | Uniroyal Inc | 2, 3-dihydro-5-carboxamido-6-methyl-1, 4-oxathins and method of making same |
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GB1518079A (en) * | 1974-06-12 | 1978-07-19 | Kumiai Chemical Industry Co | Benzanilide derivatives and their fungicidal and bactericidal uses |
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2006
- 2006-03-21 WO PCT/EP2006/002595 patent/WO2006100039A1/en not_active Application Discontinuation
- 2006-03-21 EP EP06723596A patent/EP1861374A1/en not_active Withdrawn
- 2006-03-21 AR ARP060101102A patent/AR056945A1/es not_active Application Discontinuation
- 2006-03-21 CN CN2006800092863A patent/CN101146777B/zh not_active Expired - Fee Related
- 2006-03-21 CA CA002600578A patent/CA2600578A1/en not_active Abandoned
- 2006-03-21 BR BRPI0608930-5A patent/BRPI0608930A2/pt not_active Application Discontinuation
- 2006-03-21 KR KR1020077021623A patent/KR20070113242A/ko active IP Right Grant
- 2006-03-21 JP JP2008502311A patent/JP2008538210A/ja active Pending
- 2006-03-21 MX MX2007011488A patent/MX2007011488A/es active IP Right Grant
- 2006-03-21 US US11/909,389 patent/US7767625B2/en not_active Expired - Fee Related
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US4001416A (en) * | 1974-04-09 | 1977-01-04 | Basf Aktiengesellschaft | Certain fungicidal pyridines |
US4134987A (en) * | 1976-01-14 | 1979-01-16 | Huppatz John L | Compounds and compositions |
US4742074A (en) * | 1984-10-29 | 1988-05-03 | Sumitomo Chemical Company, Limited | Pyrazolecarboxamide derivative and fungicide containing it as active ingredient |
CN1078234A (zh) * | 1991-12-06 | 1993-11-10 | 孟山都公司 | 吡唑甲酰苯胺类杀真菌剂 |
CN1161329A (zh) * | 1995-12-01 | 1997-10-08 | 拜尔公司 | 1,3-二甲基-5-氟吡唑-4-(n-苯基)甲酰胺类化合物的制法 |
WO2004018438A2 (en) * | 2002-08-22 | 2004-03-04 | Syngenta Participations Ag | Microbiocidal (e.g. fungicidal) 1,2,3-triazole derivatives |
Also Published As
Publication number | Publication date |
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MX2007011488A (es) | 2007-10-11 |
US7767625B2 (en) | 2010-08-03 |
CA2600578A1 (en) | 2006-09-28 |
EP1861374A1 (en) | 2007-12-05 |
WO2006100039A1 (en) | 2006-09-28 |
JP2008538210A (ja) | 2008-10-16 |
KR20070113242A (ko) | 2007-11-28 |
CN101146777A (zh) | 2008-03-19 |
BRPI0608930A2 (pt) | 2010-02-17 |
US20080214532A1 (en) | 2008-09-04 |
AR056945A1 (es) | 2007-11-07 |
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