CN102216294B - 具有含氮五元杂环的醚类化合物及其应用 - Google Patents
具有含氮五元杂环的醚类化合物及其应用 Download PDFInfo
- Publication number
- CN102216294B CN102216294B CN2009801381313A CN200980138131A CN102216294B CN 102216294 B CN102216294 B CN 102216294B CN 2009801381313 A CN2009801381313 A CN 2009801381313A CN 200980138131 A CN200980138131 A CN 200980138131A CN 102216294 B CN102216294 B CN 102216294B
- Authority
- CN
- China
- Prior art keywords
- nch
- alkyl
- hydrogen
- chlorine
- halo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 0 *C1=C(*)C(O*Oc(c(Cl)c2)c(*)c(*)c2OCC=C(Cl)Cl)=N*1 Chemical compound *C1=C(*)C(O*Oc(c(Cl)c2)c(*)c(*)c2OCC=C(Cl)Cl)=N*1 0.000 description 2
Classifications
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- 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
- A01N43/72—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
- A01N43/80—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 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种具有含氮五元杂环的醚类化合物,结构如通式(I)所示:
Description
技术领域
本发明属农用杀虫、杀菌剂领域。具体地涉及一种具有含氮五元杂环的醚类化合物,以及使用它们在农业或其他领域中作为杀虫、杀菌剂的应用。
背景技术
众所周知,昆虫一般不仅在农业上造成农作物生长受损,也破坏建筑物和草坪,例如由土壤昆虫(例如白蚁和蛴螬)造成的损害。
这种损害可导致相关的农作物、草坪或建筑物的数百万美元的损失。杀虫剂和杀螨剂在防治昆虫和螨虫中是有用的,但可能会对农作物例如小麦、玉米、大豆、土豆和棉花等造成显著的损害。从保护农作物出发人类需要既能防治昆虫和螨虫而且不损害农作物,同时对哺乳动物和其它活的生物无毒害作用的杀虫剂和杀螨剂。
如下专利报道了具有杀虫和杀螨活性的二卤丙烯化合物:CN1137265、CN1318535、CN1681771、CN1780818、CN1780825、CN1860874、CN101208088、US5872137、US5922880、US6071861、US20060247283、US20050288186、US20040224994、US20070142229、WO2003074498等。未见该类化合物具有杀菌活性的报道。同时人们需要不断开发结构新颖的杀虫、杀菌剂,以满足农业或其他领域中用于防治病虫害的需要。该类化合物代表品种Pyridalyl是日本住友化学株式会社的一个专利产品,对蔬菜和棉花上广泛的鳞翅目害虫具有卓效,结构式如下:
发明内容
本发明的目的在于提供一种在很小的剂量下就可以控制各种病虫害的具有含氮五元杂环的醚类化合物,它可应用于农业上以防治作物的病害和虫害,或其在他领域中作为杀虫、杀菌剂的应用。
本发明的技术方案如下:
本发明提供一种具有含氮五元杂环的醚类化合物,如通式(I)所示:
式中:
R1选自氢、CO2R6、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基C1-C12烷基、C1-C12卤代烷氧基C1-C12烷基、C3-C6环烷基或R7;
R2选自氢、卤素、CN、CO2R6、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C1-C12烷硫基、卤代C1-C12烷硫基、C3-C6环烷基或R7;
R3、R4、R5可相同或不同,分别选自氢、卤素、羟基、巯基、氰基、硝基、C1-C12烷基、卤代C1-C12烷基、C1-C12烷基羰基、C2-C12烯基、卤代C2-C12烯基、C2-C12炔基、C1-C12烷氧基、卤代C1-C12烷氧基、C2-C12烯氧基、卤代C2-C12烯氧基、C3-C12炔氧基、卤代C3-C12炔氧基、C1-C12烷硫基、卤代C1-C12烷硫基、C1-C12烷基磺酰基、C1-C12烷基亚砜基、C1-C12烷氧基C1-C12烷基、C1-C12烷氧基羰基、C1-C12烷氧基羰基C1-C12烷基或C1-C12卤代烷氧基C1-C12烷基;
X选自NR8或O;
R8选自氢、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基C1-C12烷基、C1-C12卤代烷氧基C1-C12烷基、C3-C6环烷基或R7;
Y1、Y2可相同或不同,分别选自氢、氟、氯、溴、CH3、CN或CF3;
A1、A2可相同或不同,分别选自O、S或NR6;
R6选自氢或C1-C12烷基;
R7选自芳基、杂芳基、芳基C1-C12烷基或杂芳基C1-C12烷基,或者被1-5个独立选自以下基团进一步取代的上述基团:卤素、NO2、CN、CO2R6、CONHR6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基或R7;
Q选自-CH2-、-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2CH2CH2CH2CH2-、-CH(CH3)-、-CH(CH3)CH2-、-CH(CH3)CH2CH2-、-CH2CH2CH(CH3)-、-CH(C2H5)-、-C(CH3)2-、-CH(CH3)CH(CH3)-、-CH2C(CH3)2CH2-、-CH2CH2OCH2CH2-、-CH2CH2NHCH2CH2-、-CH2CH2SCH2CH2-、-CH2CH2SO2CH2CH2-、-CH2COCH2-、-COCH2CO-、-CH2CH2CO-、-COCH2CH2-、-CH2CO-、-COCH2-、-CH2C(=NOCH3)CH2-、-CH2C(=NN(CH3)2)CH2-、-CH2CH(OH)CH2-、-CH2CH(OCH3)CH2-、-CH2CH(OCOCH3)CH2-或
A2与杂环的连接位置选自3、4或5位;当A2与杂环5位连接时,则R1在3位,R2在4位;当A2与杂环3位连接时,则R1在5位,R2在4位;当A2与杂环4位连接时,则R1在3位,R2在5位。
本发明中较为优选的化合物为:通式(I)中
R1选自氢、CO2R6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6烷基、C3-C6环烷基或R7;
R2选自氢、卤素、CN、CO2R6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C3-C6环烷基或R7;
R3、R4、R5可相同或不同,分别选自氢、卤素或C1-C6烷基;
X选自NR8或O;
R8选自氢、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6烷基、C3-C6环烷基或R7;
Y1、Y2可相同或不同,分别选自氢、氟、氯、溴、CH3、CN或CF3;
A1、A2可相同或不同,分别选自O、S或NR6;
R6选自氢或C1-C6烷基;
R7选自苯基、吡啶基、嘧啶基、三唑基、恶唑基、噻二唑基、恶二唑基、呋喃基、噻吩基、噻唑基、苄基、吡啶甲基、噻吩甲基或噻唑甲基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、NO2、CN、CO2R6、CONHR6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、苯基、对氯苯基、苯氧基或对氯苯氧基;
Q选自-CH2CH2-、-CH2CH2CH2-、-CH2CH2CH2CH2-、-CH2COCH2-或
A2与杂环的连接位置选自3、4或5位;当A2与杂环5位连接时,则R1在3位,R2在4位;当A2与杂环3位连接时,则R1在5位,R2在4位;当A2与杂环4位连接时,则R1在3位,R2在5位。
本发明进一步优选的化合物为:通式(I)中
R1选自氢、CO2R6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6烷基、C3-C6环烷基或R7;
R2选自氢、卤素、CN、CO2R6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C3-C6环烷基或R7;
R3选自氯;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8或O;
R8选自C1-C6烷基、卤代C1-C6烷基或R7;
Y1、Y2选自氯;
A1、A2选自O;
R6选自氢或C1-C6烷基;
R7选自苯基、吡啶基、呋喃基、噻吩基、噻唑基或苄基,或者被1-3个独立选自以下基团进一步取代的上述基团:卤素、NO2、CN、CO2R6、CONHR6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基磺酰基、苯基、对氯苯基、苯氧基或对氯苯氧基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
A2与杂环的连接位置选自3、4或5位;当A2与杂环5位连接时,则R1在3位,R2在4位,结构式如I-1所示;当A2与杂环3位连接时,则R1在5位,R2在4位,结构式如I-2所示;当A2与杂环4位连接时,则R1在3位,R2在5位,结构式如I-3所示;
本发明更进一步优选的化合物为:通式(I-1)或通式(I-2)中
R1选自氢、CO2R6、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基C1-C6烷基、C1-C6卤代烷氧基C1-C6烷基、C3-C6环烷基或R7;
R2选自氢、氟、氯、溴、CN、CO2R6或C1-C6烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基;
R6选自氢或C1-C4烷基;
R7选自苯基,或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基或C1-C6烷硫基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
或者,通式(I-3)中
R1选自氢、CO2R6或C1-C6烷基;
R2选自氢、氟、氯、溴或C1-C6烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基或R7;
R6选自氢或C1-C4烷基;
R7选自苯基,或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、CN、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基或C1-C6烷硫基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-。
本发明再进一步优选的化合物为:通式(I-1)或通式(I-2)中
R1选自苯基,或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基;
R2选自氢、氯或C1-C4烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基;
R6选自氢或C1-C4烷基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
或者,通式(I-3)中
R1选自氢、CO2R6或C1-C4烷基;
R2选自氢、氟、氯、溴或C1-C4烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基、苯基、或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R6选自氢或C1-C4烷基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-。
上面给出的通式(I)化合物的定义中,汇集所用术语一般定义如下:
未取代表示所有取代基都为氢。
卤:指氟、氯、溴或碘。
烷基:直链或支链烷基,例如甲基、乙基、丙基、异丙基或叔丁基。
卤代烷基:直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤原子所取代,例如,卤代烷基诸如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基或三氟甲基。
烯基:直链或支链并可在任何位置上存在有双键,例如乙烯基或烯丙基。
炔基:直链或支链并可在任何位置上存在有三键,例如乙炔基或炔丙基。
芳基以及芳烷基中的芳基部分包括苯基或萘基等。
本发明中所指杂芳基是含1个或多个N、O、S杂原子的五元环或六元环。例如吡啶、呋喃、嘧啶、吡嗪、哒嗪、三嗪、喹啉、噻唑基、苯并噻唑基、苯并呋喃等。
在本发明优选的通式(I-1)、(I-2)、(I-3)化合物中,R1、R2优选的部分基团及其取代基见表1-表9。
Q=-CH2CH2 -、-CH2CH2CH2 -、-CH2CH2CH2CH2 -
R4、R5可相同或不同,分别选自H、Cl
通式(I-1)中:当R1为苯基时,苯环上的取代基见表1;当R1为吡啶基时,吡啶环上的取代基见表2-表4;当R1为噻唑基时,噻唑环上的取代基见表5;当R1为噻吩或呋喃时,噻吩或呋喃环上的取代基见表6-表7;当R1为其他取基时,取代基见表8。
通式(I-1)中:当R2为苯基时,苯环上的取代基见表1;当R2为吡啶基时,吡啶环上的取代基见表2-表4;当R2为噻唑基时,噻唑环上的取代基见表5;当R2为噻吩或呋喃时,噻吩或呋喃环上的取代基见表6-表7;当R2为其他取基时,取代基见表9。
通式(I-2)、(I-3)中R1、R2的具体定义同通式(I-1)。
Q=-CH2CH2 -、-CH2CH2CH2 -、-CH2CH2CH2CH2 -
R4、R5可相同或不同,分别选自H、Cl
Q=-CH2CH2 -、-CH2CH2CH2 -、-CH2CH2CH2CH2 -
R4、R5可相同或不同,分别选自H、Cl
表1
R | R | R | R | R | R | R |
H | 2-NO2 | 2-SO2C2H5 | 2,3-2F | 2,3-2CH3 | 2-Cl-4-F | 4-CH3-2-Br |
2-F | 3-NO2 | 3-SO2C2H5 | 2,4-2F | 2,4-2CH3 | 2-Cl-4-Br | 4-CH3-2-Cl |
3-F | 4-NO2 | 4-SO2C2H5 | 2,5-2F | 2,5-2CH3 | 2-Cl-4-I | 2,4,6-3CH3 |
4-F | 2-SCF3 | 2-CO2CH3 | 2,6-2F | 2,6-2CH3 | 3-Cl-4-I | 2,4,6-3C2H5 |
2-Cl | 3-SCF3 | 3-CO2CH3 | 3,4-2F | 3,4-2CH3 | 4-Cl-2-Br | 2-NHCOCH3 |
3-Cl | 4-SCF3 | 4-CO2CH3 | 3,5-2F | 3,5-2CH3 | 3,4,5-3F | 3-NHCOCH3 |
4-Cl | 2-OC2H5 | 2-CO2C2H5 | 2,3-2Cl | 2,3-2C2H5 | 2,3,4-3Cl | 4-NHCOCH3 |
2-Br | 3-OC2H5 | 3-CO2C2H5 | 2,4-2Cl | 2,4-2C2H5 | 2,3,5-3Cl | 2-NHSO2CH3 |
3-Br | 4-OC2H5 | 4-CO2C2H5 | 2,5-2Cl | 2,5-2C2H5 | 2,3,6-3Cl | 3-NHSO2CH3 |
4-Br | 2-COCH3 | 2-N(CH3)2 | 2,6-2Cl | 2,6-2C2H5 | 2,4,5-3Cl | 4-NHSO2CH3 |
2-I | 3-COCH3 | 3-N(CH3)2 | 3,4-2Cl | 3,4-2C2H5 | 2,4,6-3Cl | 2-(Ph-4-Cl) |
3-I | 4-COCH3 | 4-N(CH3)2 | 3,5-2Cl | 3,5-2C2H5 | 3,4,5-3Cl | 3-(Ph-4-Cl) |
4-I | 2-CH2Ph | 2-N(C2H5)2 | 2,3-2Br | 2,3-2CF3 | 2,3,4-3Br | 4-(Ph-4-Cl) |
2-CH3 | 3-CH2Ph | 3-N(C2H5)2 | 2,4-2Br | 2,4-2CF3 | 2,3,5-3Br | 2-CH(CH3)2 |
3-CH3 | 4-CH2Ph | 4-N(C2H5)2 | 2,5-2Br | 2,5-2CF3 | 2,3,6-3Br | 3-CH(CH3)2 |
4-CH3 | 2-C(CH3)3 | 4-Ph | 2,6-2Br | 2,6-2CF3 | 2,4,5-3Br | 4-CH(CH3)2 |
2-C2H5 | 3-C(CH3)3 | 2-OPh | 3,4-2Br | 3,4-2CF3 | 2,4,6-3Br | 2-CF3-4-Cl |
3-C2H5 | 4-C(CH3)3 | 3-OPh | 3,5-2Br | 3,5-2CF3 | 3,4,5-3Br | 2-CF3-4-Br |
4-C2H5 | 2-COCH3 | 4-OPh | 2,3-2CN | 2,6-2SCF3 | 4-CH3-3-F | 3-CF3-4-NO2 |
2-CF3 | 3-COCH3 | 2,3-2OCH3 | 2,4-2CN | 3,4-2SCF3 | 4-CH3-3-Cl | 3-CF3-4-F |
3-CF3 | 4-COCH3 | 2,4-2OCH3 | 2,5-2CN | 3,5-2SCF3 | 4-CH3-3-Br | 3-CF3-4-Cl |
4-CF3 | 2-COC2H5 | 2,5-2OCH3 | 2,6-2CN | 2,3-2SCH3 | 2,4,6-3CF3 | 4-CF3-2-NO2 |
2-OCH3 | 3-COC2H5 | 2,6-2OCH3 | 3,4-2CN | 2,4-2SCH3 | 2-CH3-3-F | 4-CF3-2-Cl |
3-OCH3 | 4-COC2H5 | 3,4-2OCH3 | 3,5-2CN | 2,5-2SCH3 | 2-CH3-3-Cl | 4-CF3-2-Br |
4-OCH3 | 2-SOCH3 | 3,5-2OCH3 | 2-F-4-Cl | 2,6-2SCH3 | 2-CH3-4-F | 2-CH3-5-NO2 |
2-SCH3 | 3-SOCH3 | 3-CONH2 | 2-F-4-Br | 3,4-2SCH3 | 2-CH3-4-Cl | 2-CH3-3-NO2 |
3-SCH3 | 4-SOCH3 | 4-CONH2 | 2-F-4-I | 3,5-2SCH3 | 2-CH3-4-Br | 2-SCH3-5-Cl |
4-SCH3 | 2-SO2CH3 | 2-OCH2Ph | 2-F-5-Cl | 2,3-2OCF3 | 2-CH3-5-F | 4-SO2CH3-2Cl |
2-OCF3 | 3-SO2CH3 | 3-OCH2Ph | 3-F-5-Cl | 2,4-2OCF3 | 2-CH3-5-Cl | 2-CH3-4-NO2 |
3-OCF3 | 4-SO2CH3 | 4-OCH2Ph | 4-F-3-Cl | 2,5-2OCF3 | 2-CH3-5-Br | 2-CH3-4-OCH3 |
4-OCF3 | 2-SOC2H5 | 2,3-2NO2 | 4-F-6-Cl | 2,6-2OCF3 | 2-CH3-6-Cl | 2-CH3-6-C2H5 |
2-CN | 3-SOC2H5 | 2,4-2NO2 | 2,3,4-3F | 3,4-2OCF3 | 3-CH3-2-Br | 2-CH3-6-NO2 |
3-CN | 4-SOC2H5 | 2,5-2NO2 | 2,3,5-3F | 3,5-2OCF3 | 3-CH3-4-Cl | 2,4,6-3NO2 |
4-CN | 2-OCHF2 | 2,6-2NO2 | 2,3,6-3F | 2,3-2SCF3 | 3-CH3-4-Br | 2,3-2Cl-4-Br |
续表1
R | R | R | R | R |
3-OCHF2 | 3,4-2NO2 | 2,4,5-3F | 2,4-2SCF3 | 3-CH3-4-I |
4-OCHF2 | 3,5-2NO2 | 2,4,6-3F | 2,5-2SCF3 | 2-CH3-4-I |
5-CF3-2-Cl | 5-CF3-2-OCH3 | 4-CH3-2,6-2Br | 3-CH3-4-NHCOCH3 | 2-NO2-4-F |
5-CF3-2-Br | 2-CF3-4-NO2 | 5-CH3-4-F-6-Cl | 4-CH3-3-NHSO2CH3 | 2-NO2-4-Cl |
2-CN-3-F | 2,4-2NO2-6-Cl | 4-C(CH3)3-2-Cl | 4-CH3-3-OCH2Ph-6-Br | 2-NO2-4-Br |
2-CN-3-Cl | 2,4-2NO2-6-Br | 4-CF3-2-Cl-6-Br | 5-CH3-2-OCH3-4-Cl | 2-NO2-5-Cl |
2-CN-4-NO2 | 2,3-2CH(CH3)2 | 2-COOCH3-4-Br | 4-COCH3-2,6-2Cl | 3-NO2-4-Cl |
2-CN-4-Cl | 2,4-2CH(CH3)2 | 4-COOCH3-2-Cl | 5-CF3-2-NHCOCH3 | 3-NO2-4-Br |
2-CN-4-Br | 2,5-2CH(CH3)2 | 4-COOCH3-2-Br | 2-CH3-4-NO2-6-Cl | 4-NO2-2-Cl |
4-CN-2-CF3 | 2,6-2CH(CH3)2 | 2,4,6-3CH(CH3)2 | 2-CH3-4-NO2-6-Br | 5-NO2-2-Cl |
4-CN-2-Cl | 3,4-2CH(CH3)2 | 2,4,6-3C(CH3)3 | 2-CH3-6-NO2-4-Cl | 5-NO2-2-Br |
4-CN-2-NO2 | 3,5-2CH(CH3)2 | 2,3-2CH3-6-NO2 | 2-CH3-6-NO2-4-Br | 2-OCH3-5-Cl |
5-CH3-2-F | 2-NO2-4-OCH3 | 2,4-2OCH3-5-Cl | 2,5-2OCH3-4-NO2 | 4-OCH3-3-F |
4-CH3-2-NO2 | 2-NO2-4-OC2H5 | 5-CONH2-2-Cl | 2,6-2CH3-4-C(CH3)3 | 4-OCH3-3-Cl |
4-CH3-3-NO2 | 2,3-2C(CH3)3 | 4-N(CH3)2-2-NO2 | 4-CF3-2-NO2-5-Cl | 3-NO2-4-F |
5-CH3-2-CN | 2,4-2C(CH3)3 | 5-N(CH3)2-2-NO2 | 4-CF3-2-NO2-6-Cl | 2-OCF3-4-CN |
5-NO2-2-F | 2,5-2C(CH3)3 | 4,5-2CH3-2-NO2 | 4-CF3-2-NO2-6-Br | 2-OCF3-4-Cl |
2-CF3-4,6-2Cl | 2,6-2C(CH3)3 | 2-NO2-4-F-5-Cl | 5-CH3-2-CONH2 | 2-OCF3-4-Br |
2-CF3-4,6-2Br | 3,4-2C(CH3)3 | 2-CN-4-NO2-6-Cl | 2-CH3-5-CONH2 | 2-F-4,6-2Br |
3-CH3-2,6-2Cl | 3,5-2C(CH3)3 | 2-CN-4-NO2-6-Br | 2,4-2F-6-Cl | 4-OCF3-2-Cl |
2-CH3-4,6-2Br | 4-SO2NH2 | 2-OCH2CH=CH2 | 4-O(CH2)2N(CH3)2 | 4-OCF3-2-Br |
2,4,6-3OCH3 | 4-NO2-2-OCH3 | 3-OCH2CH=CH2 | 4-CH3-3-OCH2Ph | 2,3,5,6-4F |
3,4,5-3OCH3 | 2-CH2CH=CH2 | 4-OCH2CH=CH2 | 2-CH2C(CH3)=CH2 | 2-CN-4,6-2Cl |
2,4,6-3SCH3 | 3-CH2CH=CH2 | 2-OCH2C≡CH | 3-CH2C(CH3)=CH2 | 2-CN-4,6-2Br |
2,4,6-3OCF3 | 4-CH2CH=CH2 | 3-OCH2C≡CH | 4-CH2C(CH3)=CH2 | 4-CN-2,6-2Cl |
2,4,6-3SCF3 | 2-C(CH3)=CH2 | 4-OCH2C≡CH | 4-O(CH2)3CH3-2-NO2 | 4-CF3-2,6-2Cl |
2-CH2C≡CH | 3-C(CH3)=CH2 | 5-NO2-2-OCH3 | 3-OCH3-4-CO2CH3 | 4-CF3-2,6-2Br |
3-CH2C≡CH | 4-C(CH3)=CH2 | 5-CH3-2-OCH3 | 2-CH(CH3)CH2CH(CH3)2 | 2,3,4,5,6-5Cl |
4-CH2C≡CH | 4-F-2,6-2Br | 4-NO2-2,6-2Cl | 2,3-(CH2CH2CH2-) | 2,3-(OCF2O-) |
2-F-3-Cl | 2,4-2F-6-Cl | 4-OCF3-2-NO2 | 2,3-(CH2CH2CH2CH2-) | 2,3-(OCH2O-) |
3-CH3-2-Cl | 2-F-4-Cl-6-Br | 6-NO2-2,3,4-3F | 4-NO2-2,5-2Cl | 3,4-(OCH2O-) |
4-O(CH2)3CH3 | 2,3,5,6-4F-4-CF3 | 4-NO2-2,6-2Br | 4-F-3-Cl-2,6-2Br | 3,4-(OCF2O-) |
4-Ph | 4-(4-Cl-Ph) | 2-Ph | 3-Ph | 4-(4-Br-Ph) |
4-(4-F-Ph) | 4-(4-CH3-Ph) | 4-(4-OCH3-Ph) | 4-(4-CF3-Ph) | 4-(4-CN-Ph) |
4-(4-NO2-Ph) | 4-(2-CH3-Ph) | 4-(2-Cl-Ph) | 4-(3-Cl-Ph) | 4-OPh |
4-O(Ph-4-Cl) | 4-O(Ph-4-Br) | 4-O(Ph-4-F) | 4-O(Ph-4-CH3) | 2-OPh |
表2
R | R | R | R | R |
H | 3-Br | 6-OCH3 | 3-CH3-5-NO2 | 6-CH3-3,5-2Br |
3-CH3 | 4-Br | 5-OCH3 | 4-CH3-3-NO2 | 3-CONH2-4,6-2Cl |
4-CH3 | 5-Br | 3,5-2Cl | 4-CH3-5-NO2 | 4-CH3-5-NO2-3-Br |
5-CH3 | 6-Br | 3,5-2Br | 5-CH3-3-NO2 | 3-CN-4,6-2Cl |
6-CH3 | 5-I | 4-CH3-5-Br | 6-CH3-4-NO2 | 3-CN-4-CH3-6-Cl |
3-Cl | 5-F | 6-CH3-5-CN | 6-CH3-5-NO2 | 3-CN-4-CF3-6-Cl |
4-Cl | 6-F | 3,5,6-3Cl | 3-NO2-5-Cl | 4-CH3-5-CN-6-Cl |
5-Cl | 3-CN | 3-CO2CH3 | 3-NO2-5-Br | 4-CF3-5-CN-6-Cl |
6-Cl | 4-CN | 5-CO2CH3 | 5-NO2-3-Br | 3-CO2CH3-6-Cl |
3-CF3 | 5-CN | 3-OCH2Ph | 5-CH3-3-Br | 5-CO2CH3-6-Cl |
4-CF3 | 6-CN | 5-CF3-3-Cl | 6-CH3-5-Br | 5-CF3-3,6-2Cl |
5-CF3 | 3-NO2 | 5-CN-3-Cl | 3-CH3-5-Br | 5-CF3-6-Cl |
6-CF3 | 5-NO2 | 5-CH3-3-Cl | 3-CF3-6-Cl | 3-CN-6-Cl |
表3
表4
R | R | R | R | R |
H | 3-Cl | 2-OCH3 | 2,6-2Cl | 2-OCH3-6-Cl |
2-Cl | 2-Br | 2,6-2OCH3 | 6-OPh | 2-NHCH3-6-Cl |
表5
R | R | R | R | R |
H | 5-NO2 | 4-CO2C2H5 | 4-CH3-5-COCH3 | 4-(Ph-4-Cl)-5-CO2C2H5 |
5-Cl | 5-OPh | 4-(Ph-3,4-2F) | 4-CH3-5-CO2C2H5 | 4,5-(CCl=CH-CH=CH-) |
5-CH3 | 5-OCH3 | 4-(Ph-4-Cl) | 4-CF3-5-CO2C2H5 | 4,5-(CH=CCl-CH=CH-) |
4-Cl | 4,5-2Cl | 4,5-(CH2-)3 | 5-CH3-4-CO2C2H5 | 4,5-(CH=CH-CCl=CH-) |
5-Br | 4,5-2CH3 | 4,5-(CH2-)4 | 5-Ph-4-CO2C2H5 | 4,5-(CMe=CH-CH=CH-) |
4-CH3 | 4-C(CH3)3 | 4-CF3-5-CN | 4-CH3-5-CONHCH3 | 4,5-(CH=CMe-CH=CH-) |
5-Ph | 5-(Ph-4-Cl) | 4-CH2CO2C2H5 | 4-CF3-5-CONHCH3 | 4,5-(C(OMe)=CH-CH=CH-) |
4-Ph | 4-(Ph-4-Br) | 4-Ph-5-CO2C2H5 | 4,5-(CH=CH-CH=CH-) | 4,5-(CH=C(OMe)-CH=CH-) |
表6
R | R | R | R | R |
H | 5-NO2 | 4-CO2C2H5 | 4-CH3-5-COCH3 | 4-(Ph-4-Cl)-5-CO2C2H5 |
5-Cl | 5-OPh | 4-(Ph-3,4-2F) | 4-CH3-5-CO2C2H5 | 4,5-(CCl=CH-CH=CH-) |
5-CH3 | 5-OCH3 | 4-(Ph-4-Cl) | 4-CF3-5-CO2C2H5 | 4,5-(CH=CCl-CH=CH-) |
4-Cl | 4,5-2Cl | 4,5-(CH2-)3 | 5-CH3-4-CO2C2H5 | 4,5-(CH=CH-CCl=CH-) |
3-Cl | 3-CH3 | 3-OCH3 | 3-NO2 | 3,4-2CH3 |
5-Br | 4,5-2CH3 | 4,5-(CH2-)4 | 5-Ph-4-CO2C2H5 | 4,5-(CMe=CH-CH=CH-) |
3-Br | 3-Ph | 3-OPh | 3,5-2CH3 | 3-CH3-5-COCH3 |
3-(Ph-4-Cl) | 3-(Ph-3,4-2F) | 3-CO2C2H5 | 3-CF3-5-CN | 3-CH2CO2C2H5 |
4-CH3 | 4-C(CH3)3 | 4-CF3-5-CN | 4-CH3-5-CONHCH3 | 4,5-(CH=CMe-CH=CH-) |
3-CF3-5-CO2C2H5 | 3-COCH3-4-CH3 | 3-CO2C2H5-4-CF3 | 3,4-(CH=CH-CH=CH-) | 3,4-(CH2-)4 |
5-Ph | 5-(Ph-4-Cl) | 4-CH2CO2C2H5 | 4-CF3-5-CONHCH3 | 4,5-(C(OMe)=CH-CH=CH-) |
4-Ph | 4-(Ph-4-Br) | 4-Ph-5-CO2C2H5 | 4,5-(CH=CH-CH=CH-) | 4,5-(CH=C(OMe)-CH=CH-) |
表7
R | R | R | R | R |
H | 5-NO2 | 4-CO2C2H5 | 4-CH3-5-COCH3 | 4-(Ph-4-Cl)-5-CO2C2H5 |
5-Cl | 5-OPh | 4-(Ph-3,4-2F) | 4-CH3-5-CO2C2H5 | 4,5-(CCl=CH-CH=CH-) |
5-CH3 | 5-OCH3 | 4-(Ph-4-Cl) | 4-CF3-5-CO2C2H5 | 4,5-(CH=CCl-CH=CH-) |
4-Cl | 4,5-2Cl | 4,5-(CH2-)3 | 5-CH3-4-CO2C2H5 | 4,5-(CH=CH-CCl=CH-) |
2-Cl | 2-CH3 | 2-OCH3 | 2-NO2 | 2,4-2CH3 |
5-Br | 4,5-2CH3 | 4,5-(CH2-)4 | 5-Ph-4-CO2C2H5 | 4,5-(CMe=CH-CH=CH-) |
2-Br | 2-Ph | 2-OPh | 2,5-2CH3 | 2-CH3-5-COCH3 |
2-(Ph-4-Cl) | 2-(Ph-3,4-2F) | 2-CO2C2H5 | 2-CF3-5-CN | 2-CH2CO2C2H5 |
4-CH3 | 4-C(CH3)3 | 4-CF3-5-CN | 4-CH3-5-CONHCH3 | 4,5-(CH=CMe-CH=CH-) |
2-CF3-5-CO2C2H5 | 2-COCH3-4-CH3 | 2-CO2C2H5-4-CF3 | 2,5-2Cl | 2,4-2Cl |
5-Ph | 5-(Ph-4-Cl) | 4-CH2CO2C2H5 | 4-CF3-5-CONHCH3 | 4,5-(C(OMe)=CH-CH=CH-) |
4-Ph | 4-(Ph-4-Br) | 4-Ph-5-CO2C2H5 | 4,5-(CH=CH-CH=CH-) | 4,5-(CH=C(OMe)-CH=CH-) |
表8
表9
部分化合物可以用表10、表11、表12中列出的具体化合物来说明本发明,但并不限定本发明。
表10
编号 | X | R1 | R2 | R4 | R5 | Q |
1 | NCH3 | C6H5 | H | Cl | H | -CH2CH2CH2- |
2 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
3 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2- |
4 | NCH3 | 4-NO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
5 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2- |
6 | NCH3 | 4-CN-C6H4 | H | Cl | H | -CH2CH2CH2- |
7 | NCH3 | 4-CH3CO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
8 | NCH3 | 4-CH3S-C6H4 | H | Cl | H | -CH2CH2CH2- |
9 | NCH3 | 4-CH3SO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
10 | NCH3 | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
11 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
12 | NCH(CH3)2 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
13 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
14 | NCH3 | 2-Cl-4-F-C6H3 | H | Cl | H | -CH2CH2CH2- |
15 | NCH3 | 3-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
16 | NCH3 | 4-Br-C6H4 | H | Cl | H | -CH2CH2CH2- |
17 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2CH2- |
18 | NCH3 | 4-C2H5-C6H4 | H | Cl | H | -CH2CH2CH2- |
19 | NCH3 | 4-CF3CH2O-C6H4 | H | Cl | H | -CH2CH2CH2- |
20 | NCH3 | 4-PhO-C6H4 | H | Cl | H | -CH2CH2CH2- |
21 | NCH3 | 2-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
22 | NCH3 | 3,4-2CH3O-C6H3 | H | Cl | H | -CH2CH2CH2- |
23 | NCH3 | 3,5-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
24 | NCH3 | 2-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
25 | NCH3 | 2,5-2CH3-Thiophen-3-yl | H | Cl | H | -CH2CH2CH2- |
26 | NCH3 | 2,4-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
27 | NCH3 | 3,4-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
28 | NCH3 | 2,5-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
29 | NCH3 | 2,6-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
30 | NCH3 | 6-CH3O-Pyridin-3-yl | H | Cl | H | -CH2CH2CH2- |
31 | NCH3 | 6-CF3CH2O-Pyridin-3-yl | H | Cl | H | -CH2CH2CH2- |
32 | NCH3 | 4-(4-Cl-Ph)-C6H4 | H | Cl | H | -CH2CH2CH2- |
33 | NCH3 | Thiophen-2-yl | H | Cl | H | -CH2CH2CH2- |
34 | NCH3 | 5-Cl-Thiophen-2-yl | H | Cl | H | -CH2CH2CH2- |
35 | NCH3 | Thiazol-2-yl | H | Cl | H | -CH2CH2CH2- |
36 | NCH3 | Furan-2-yl | H | Cl | H | -CH2CH2CH2- |
37 | NCH3 | 4-i-C3H7-C6H4 | H | Cl | H | -CH2CH2CH2- |
38 | NCH3 | 4-n-C3H7-C6H4 | H | Cl | H | -CH2CH2CH2- |
39 | NCH3 | 4-t-C4H9-C6H4 | H | Cl | H | -CH2CH2CH2- |
40 | NCH3 | 2,4,6-3CH3-C6H2 | H | Cl | H | -CH2CH2CH2- |
41 | NCH3 | 2,4,6-3Cl-C6H2 | H | Cl | H | -CH2CH2CH2- |
42 | NCH3 | C6H5 | Cl | Cl | H | -CH2CH2CH2- |
43 | NCH3 | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
44 | NCH3 | 4-F-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
45 | NCH3 | 4-NO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
46 | NCH3 | 4-CF3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
47 | NCH3 | 4-CN-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
48 | NCH3 | 4-CH3CO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
49 | NCH3 | 4-CH3S-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
50 | NCH3 | 4-CH3SO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
51 | NCH3 | 4-CF3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
52 | NCH3 | 2,4-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
53 | NCH(CH3)2 | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
54 | NCH3 | 4-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
55 | NCH3 | 2-Cl-4-F-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
56 | NCH3 | 3-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
57 | NCH3 | 4-Br-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
58 | NCH3 | 4-CH3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
59 | NCH3 | 4-C2H5-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
60 | NCH3 | 4-CF3CH2O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
61 | NCH3 | 4-PhO-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
62 | NCH3 | 2-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
63 | NCH3 | 3,4-2CH3O-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
64 | NCH3 | 3,5-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
65 | NCH3 | 2-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
66 | NCH3 | 2,5-2CH3-Thiophen-3-yl | Cl | Cl | H | -CH2CH2CH2- |
67 | NCH3 | 2,4-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
68 | NCH3 | 3,4-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
69 | NCH3 | 2,5-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
70 | NCH3 | 2,6-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
71 | NCH3 | 4-i-C3H7-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
72 | NCH3 | 4-n-C3H7-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
73 | NCH3 | 4-t-C4H9-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
74 | NCH3 | 2,4,6-3CH3-C6H2 | Cl | Cl | H | -CH2CH2CH2- |
75 | NCH3 | 2,4,6-3Cl-C6H2 | Cl | Cl | H | -CH2CH2CH2- |
76 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
77 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
78 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
79 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
80 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
81 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
82 | NCH3 | 4-CH3CO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
83 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
84 | NCH3 | 4-CH3SO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
85 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
86 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
87 | NCH(CH3)2 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
88 | NCH3 | 4-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
89 | NCH3 | 2-Cl-4-F-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
90 | NCH3 | 3-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
91 | NCH3 | 4-Br-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
92 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
93 | NCH3 | 4-C2H5-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
94 | NCH3 | 4-CF3CH2O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
95 | NCH3 | 4-PhO-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
96 | NCH3 | 2-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
97 | NCH3 | 3,4-2CH3O-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
98 | NCH3 | 3,5-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
99 | NCH3 | 2-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
100 | NCH3 | 2,5-2CH3-Thiophen-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
101 | NCH3 | 2,4-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
102 | NCH3 | 3,4-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
103 | NCH3 | 2,5-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
104 | NCH3 | 2,6-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
105 | NCH3 | 6-CH3O-Pyridin-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
106 | NCH3 | 6-CF3CH2O-Pyridin-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
107 | NCH3 | 4-(4-Cl-Ph)-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
108 | NCH3 | Thiophen-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
109 | NCH3 | 5-Cl-Thiophen-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
110 | NCH3 | Thiazol-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
111 | NCH3 | Furan-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
112 | NCH3 | 4-i-C3H7-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
113 | NCH3 | 4-n-C3H7-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
114 | NCH3 | 4-t-C4H9-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
115 | NCH3 | 2,4,6-3CH3-C6H2 | CH3 | Cl | H | -CH2CH2CH2- |
116 | NCH3 | 2,4,6-3Cl-C6H2 | CH3 | Cl | H | -CH2CH2CH2- |
117 | NCH3 | C6H5 | CO2Me | Cl | H | -CH2CH2CH2- |
118 | NCH3 | 4-Cl-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
119 | NCH3 | 4-F-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
120 | NCH3 | 4-NO2-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
121 | NCH3 | 4-CF3-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
122 | NCH3 | 4-CN-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
123 | NCH3 | 4-CH3CO2-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
124 | NCH3 | 4-CH3S-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
125 | NCH3 | 4-CF3O-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
126 | NCH3 | 2,4-2Cl-C6H3 | CO2Me | Cl | H | -CH2CH2CH2- |
127 | NCH(CH3)2 | 4-Cl-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
128 | NCH3 | 4-CH3O-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
129 | NC2H5 | C6H5 | H | Cl | H | -CH2CH2CH2- |
130 | NC2H5 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
131 | NC4H9-n | C6H5 | H | Cl | H | -CH2CH2CH2- |
132 | NC4H9-n | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
133 | NC2H5 | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
134 | NC2H5 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
135 | NC4H9-n | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
136 | NC4H9-n | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
137 | NCH3 | C6H5 | H | H | H | -CH2CH2CH2- |
138 | NCH3 | 4-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
139 | NCH3 | 4-F-C6H4 | H | H | H | -CH2CH2CH2- |
140 | NCH3 | 4-CF3-C6H4 | H | H | H | -CH2CH2CH2- |
141 | NCH3 | 4-CH3S-C6H4 | H | H | H | -CH2CH2CH2- |
142 | NCH3 | 2,4-2Cl-C6H3 | H | H | H | -CH2CH2CH2- |
143 | NCH3 | 4-CH3O-C6H4 | H | H | H | -CH2CH2CH2- |
144 | NCH3 | 3-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
145 | NCH3 | 4-Br-C6H4 | H | H | H | -CH2CH2CH2- |
146 | NCH3 | 2-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
147 | NCH3 | C6H5 | H | Cl | Cl | -CH2CH2CH2- |
148 | NCH3 | 4-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
149 | NCH3 | 4-CF3-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
150 | NCH3 | 4-CH3S-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
151 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | Cl | -CH2CH2CH2- |
152 | NCH3 | 4-CH3O-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
153 | NCH3 | 3-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
154 | NCH3 | 4-Br-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
155 | NCH3 | 2-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
156 | NCH3 | C6H5 | CH3 | H | H | -CH2CH2CH2- |
157 | NCH3 | 4-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
158 | NCH3 | 4-F-C6H4 | CH3 | H | H | -CH2CH2CH2- |
159 | NCH3 | 4-CF3-C6H4 | CH3 | H | H | -CH2CH2CH2- |
160 | NCH3 | 4-CH3S-C6H4 | CH3 | H | H | -CH2CH2CH2- |
161 | NCH3 | 2,4-2Cl-C6H3 | CH3 | H | H | -CH2CH2CH2- |
162 | NCH3 | 4-CH3O-C6H4 | CH3 | H | H | -CH2CH2CH2- |
163 | NCH3 | 3-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
164 | NCH3 | 4-Br-C6H4 | CH3 | H | H | -CH2CH2CH2- |
165 | NCH3 | 2-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
166 | NCH3 | C6H5 | CH3 | Cl | Cl | -CH2CH2CH2- |
167 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
168 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
169 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
170 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | Cl | -CH2CH2CH2- |
171 | NCH3 | 4-CH3O-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
172 | NCH3 | 3-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
173 | NCH3 | 4-Br-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
174 | NCH3 | 2-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
175 | O | C6H5 | H | Cl | H | -CH2CH2CH2- |
176 | O | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
177 | O | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2- |
178 | O | 4-NO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
179 | O | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2- |
180 | O | 4-CN-C6H4 | H | Cl | H | -CH2CH2CH2- |
181 | O | 4-CH3CO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
182 | O | 4-CH3S-C6H4 | H | Cl | H | -CH2CH2CH2- |
183 | O | 4-CH3SO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
184 | O | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
185 | O | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
186 | O | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
187 | O | 2-Cl-4-F-C6H3 | H | Cl | H | -CH2CH2CH2- |
188 | O | 3-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
189 | O | 4-Br-C6H4 | H | Cl | H | -CH2CH2CH2- |
190 | O | C6H5 | Cl | Cl | H | -CH2CH2CH2- |
191 | O | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
192 | O | 4-F-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
193 | O | 4-NO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
194 | O | 4-CF3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
195 | O | 4-CN-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
196 | O | 4-CH3CO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
197 | O | 4-CH3S-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
198 | O | 4-CH3SO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
199 | O | 4-CF3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
200 | O | 2,4-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
201 | O | 4-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
202 | O | 2-Cl-4-F-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
203 | O | 3-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
204 | O | 4-Br-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
205 | O | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
206 | O | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
207 | O | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
208 | O | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
209 | O | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
210 | O | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
211 | O | 4-CH3CO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
212 | O | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
213 | O | 4-CH3SO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
214 | O | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
215 | O | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
216 | O | 4-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
217 | O | 3-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
218 | O | 4-Br-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
219 | O | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
220 | NPh | CF3 | H | Cl | H | -CH2CH2CH2- |
221 | N(Ph-4-Cl) | C6H5 | H | Cl | H | -CH2CH2CH2- |
222 | NCH3 | CF3 | Ph | Cl | H | -CH2CH2CH2- |
223 | NCH3 | C6H5 | Ph | Cl | H | -CH2CH2CH2- |
224 | NCH3 | C6H5 | H | Cl | H | -CH2CH2- |
225 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2- |
226 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2- |
227 | NCH3 | 4-NO2-C6H4 | H | Cl | H | -CH2CH2- |
228 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2- |
229 | NCH3 | 4-CN-C6H4 | H | Cl | H | -CH2CH2- |
230 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2- |
231 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2- |
232 | NCH3 | 4-CH3CH2-C6H4 | H | Cl | H | -CH2CH2- |
233 | NCH3 | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2- |
234 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2- |
235 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2- |
236 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2- |
237 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2- |
238 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2- |
239 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2- |
240 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2- |
241 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2- |
242 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2- |
243 | NCH3 | 4-CH3CH2-C6H4 | CH3 | Cl | H | -CH2CH2- |
244 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2- |
245 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2- |
246 | NCH3 | C6H5 | H | Cl | H | -CH2CH2CH2CH2- |
247 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
248 | NCH3 | 4-Cl-C6H4 | H | H | H | -CH2CH2CH2CH2- |
249 | NCH3 | C6H5 | H | H | H | -CH2CH2CH2CH2- |
250 | NCH3 | C6H5 | H | Cl | Cl | -CH2CH2CH2CH2- |
251 | NCH3 | 4-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2CH2- |
252 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
253 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
254 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
255 | NCH3 | 4-CH3CH2-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
256 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2CH2- |
257 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2CH2CH2- |
258 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
259 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
260 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
261 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
262 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
263 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
264 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
265 | NCH3 | 4-CH3CH2-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
266 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
267 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2CH2- |
表11
编号 | X | R1 | R2 | R4 | R5 | Q |
268 | NCH3 | C6H5 | H | Cl | H | -CH2CH2CH2- |
269 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
270 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2- |
271 | NCH3 | 4-NO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
272 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2- |
273 | NCH3 | 4-CN-C6H4 | H | Cl | H | -CH2CH2CH2- |
274 | NCH3 | 4-CH3CO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
275 | NCH3 | 4-CH3S-C6H4 | H | Cl | H | -CH2CH2CH2- |
276 | NCH3 | 4-CH3SO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
277 | NCH3 | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
278 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
279 | NCH(CH3)2 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
280 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
281 | NCH3 | 2-Cl-4-F-C6H3 | H | Cl | H | -CH2CH2CH2- |
282 | NCH3 | 3-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
283 | NCH3 | 4-Br-C6H4 | H | Cl | H | -CH2CH2CH2- |
284 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2CH2- |
285 | NCH3 | 4-C2H5-C6H4 | H | Cl | H | -CH2CH2CH2- |
286 | NCH3 | 4-CF3CH2O-C6H4 | H | Cl | H | -CH2CH2CH2- |
287 | NCH3 | 4-PhO-C6H4 | H | Cl | H | -CH2CH2CH2- |
288 | NCH3 | 2-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
289 | NCH3 | 3,4-2CH3O-C6H3 | H | Cl | H | -CH2CH2CH2- |
290 | NCH3 | 3,5-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
291 | NCH3 | 2-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
292 | NCH3 | 2,5-2CH3-Thiophen-3-yl | H | Cl | H | -CH2CH2CH2- |
293 | NCH3 | 2,4-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
294 | NCH3 | 3,4-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
295 | NCH3 | 2,5-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
296 | NCH3 | 2,6-2CH3-C6H3 | H | Cl | H | -CH2CH2CH2- |
297 | NCH3 | 6-CH3O-Pyridin-3-yl | H | Cl | H | -CH2CH2CH2- |
298 | NCH3 | 6-CF3CH2O-Pyridin-3-yl | H | Cl | H | -CH2CH2CH2- |
299 | NCH3 | 4-(4-Cl-Ph)-C6H4 | H | Cl | H | -CH2CH2CH2- |
300 | NCH3 | Thiophen-2-yl | H | Cl | H | -CH2CH2CH2- |
301 | NCH3 | 5-Cl-Thiophen-2-yl | H | Cl | H | -CH2CH2CH2- |
302 | NCH3 | Thiazol-2-yl | H | Cl | H | -CH2CH2CH2- |
303 | NCH3 | Furan-2-yl | H | Cl | H | -CH2CH2CH2- |
304 | NCH3 | 4-i-C3H7-C6H4 | H | Cl | H | -CH2CH2CH2- |
305 | NCH3 | 4-n-C3H7-C6H4 | H | Cl | H | -CH2CH2CH2- |
306 | NCH3 | 4-t-C4H9-C6H4 | H | Cl | H | -CH2CH2CH2- |
307 | NCH3 | 2,4,6-3CH3-C6H2 | H | Cl | H | -CH2CH2CH2- |
308 | NCH3 | 2,4,6-3Cl-C6H2 | H | Cl | H | -CH2CH2CH2- |
309 | NCH3 | C6H5 | Cl | Cl | H | -CH2CH2CH2- |
310 | NCH3 | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
311 | NCH3 | 4-F-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
312 | NCH3 | 4-NO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
313 | NCH3 | 4-CF3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
314 | NCH3 | 4-CN-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
315 | NCH3 | 4-CH3CO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
316 | NCH3 | 4-CH3S-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
317 | NCH3 | 4-CH3SO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
318 | NCH3 | 4-CF3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
319 | NCH3 | 2,4-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
320 | NCH(CH3)2 | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
321 | NCH3 | 4-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
322 | NCH3 | 2-Cl-4-F-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
323 | NCH3 | 3-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
324 | NCH3 | 4-Br-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
325 | NCH3 | 4-CH3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
326 | NCH3 | 4-C2H5-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
327 | NCH3 | 4-CF3CH2O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
328 | NCH3 | 4-PhO-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
329 | NCH3 | 2-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
330 | NCH3 | 3,4-2CH3O-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
331 | NCH3 | 3,5-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
332 | NCH3 | 2-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
333 | NCH3 | 2,5-2CH3-Thiophen-3-yl | Cl | Cl | H | -CH2CH2CH2- |
334 | NCH3 | 2,4-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
335 | NCH3 | 3,4-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
336 | NCH3 | 2,5-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
337 | NCH3 | 2,6-2CH3-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
338 | NCH3 | 6-CH3O-Pyridin-3-yl | Cl | Cl | H | -CH2CH2CH2- |
339 | NCH3 | 6-CF3CH2O-Pyridin-3-yl | Cl | Cl | H | -CH2CH2CH2- |
340 | NCH3 | 4-(4-Cl-Ph)-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
341 | NCH3 | Thiophen-2-yl | Cl | Cl | H | -CH2CH2CH2- |
342 | NCH3 | 5-Cl-Thiophen-2-yl | Cl | Cl | H | -CH2CH2CH2- |
343 | NCH3 | Thiazol-2-yl | Cl | Cl | H | -CH2CH2CH2- |
344 | NCH3 | Furan-2-yl | Cl | Cl | H | -CH2CH2CH2- |
345 | NCH3 | 4-i-C3H7-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
346 | NCH3 | 4-n-C3H7-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
347 | NCH3 | 4-t-C4H9-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
348 | NCH3 | 2,4,6-3CH3-C6H2 | Cl | Cl | H | -CH2CH2CH2- |
349 | NCH3 | 2,4,6-3Cl-C6H2 | Cl | Cl | H | -CH2CH2CH2- |
350 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
351 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
352 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
353 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
354 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
355 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
356 | NCH3 | 4-CH3CH2O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
357 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
358 | NCH3 | 4-CH3SO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
359 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
360 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
361 | NCH3 | 3,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
362 | NCH(CH3)2 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
363 | NCH3 | 4-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
364 | NCH3 | 2-Cl-4-F-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
365 | NCH3 | 3-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
366 | NCH3 | 4-Br-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
367 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
368 | NCH3 | 4-C2H5-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
369 | NCH3 | 4-CF3CH2O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
370 | NCH3 | 4-PhO-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
371 | NCH3 | 2-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
372 | NCH3 | 3,4-2CH3O-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
373 | NCH3 | 3,5-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
374 | NCH3 | 2-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
375 | NCH3 | 2,5-2CH3-Thiophen-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
376 | NCH3 | 2,4-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
377 | NCH3 | 3,4-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
378 | NCH3 | 2,5-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
379 | NCH3 | 2,6-2CH3-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
380 | NCH3 | 6-CH3O-Pyridin-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
381 | NCH3 | 6-CF3CH2O-Pyridin-3-yl | CH3 | Cl | H | -CH2CH2CH2- |
382 | NCH3 | 4-(4-Cl-Ph)-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
383 | NCH3 | Thiophen-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
384 | NCH3 | 5-Cl-Thiophen-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
385 | NCH3 | Thiazol-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
386 | NCH3 | Furan-2-yl | CH3 | Cl | H | -CH2CH2CH2- |
387 | NCH3 | 4-i-C3H7-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
388 | NCH3 | 4-n-C3H7-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
389 | NCH3 | 4-t-C4H9-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
390 | NCH3 | 2,4,6-3CH3-C6H2 | CH3 | Cl | H | -CH2CH2CH2- |
391 | NCH3 | 2,4,6-3Cl-C6H2 | CH3 | Cl | H | -CH2CH2CH2- |
392 | NCH3 | C6H5 | CO2Me | Cl | H | -CH2CH2CH2- |
393 | NCH3 | 4-Cl-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
394 | NCH3 | 4-F-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
395 | NCH3 | 4-NO2-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
396 | NCH3 | 4-CF3-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
397 | NCH3 | 4-CN-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
398 | NCH3 | 4-CH3S-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
399 | NCH3 | 4-CH3SO2-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
400 | NCH3 | 4-CF3O-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
401 | NCH3 | 2,4-2Cl-C6H3 | CO2Me | Cl | H | -CH2CH2CH2- |
402 | NCH(CH3)2 | 4-Cl-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
403 | NCH3 | 4-CH3O-C6H4 | CO2Me | Cl | H | -CH2CH2CH2- |
404 | NC2H5 | C6H5 | H | Cl | H | -CH2CH2CH2- |
405 | NC2H5 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
406 | NC4H9-n | C6H5 | H | Cl | H | -CH2CH2CH2- |
407 | NC4H9-n | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
408 | NC2H5 | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
409 | NC2H5 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
410 | NC4H9-n | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
411 | NC4H9-n | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
412 | NCH3 | C6H5 | H | H | H | -CH2CH2CH2- |
413 | NCH3 | 4-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
414 | NCH3 | 4-F-C6H4 | H | H | H | -CH2CH2CH2- |
415 | NCH3 | 4-CF3-C6H4 | H | H | H | -CH2CH2CH2- |
416 | NCH3 | 4-CH3S-C6H4 | H | H | H | -CH2CH2CH2- |
417 | NCH3 | 2,4-2Cl-C6H3 | H | H | H | -CH2CH2CH2- |
418 | NCH3 | 4-CH3O-C6H4 | H | H | H | -CH2CH2CH2- |
419 | NCH3 | 3-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
420 | NCH3 | 4-Br-C6H4 | H | H | H | -CH2CH2CH2- |
421 | NCH3 | 2-Cl-C6H4 | H | H | H | -CH2CH2CH2- |
422 | NCH3 | C6H5 | H | Cl | Cl | -CH2CH2CH2- |
423 | NCH3 | 4-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
424 | NCH3 | 4-CF3-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
425 | NCH3 | 4-CH3S-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
426 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | Cl | -CH2CH2CH2- |
427 | NCH3 | 4-CH3O-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
428 | NCH3 | 3-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
429 | NCH3 | 4-Br-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
430 | NCH3 | 2-Cl-C6H4 | H | Cl | Cl | -CH2CH2CH2- |
431 | NCH3 | C6H5 | CH3 | H | H | -CH2CH2CH2- |
432 | NCH3 | 4-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
433 | NCH3 | 4-F-C6H4 | CH3 | H | H | -CH2CH2CH2- |
434 | NCH3 | 4-CF3-C6H4 | CH3 | H | H | -CH2CH2CH2- |
435 | NCH3 | 4-CH3S-C6H4 | CH3 | H | H | -CH2CH2CH2- |
436 | NCH3 | 2,4-2Cl-C6H3 | CH3 | H | H | -CH2CH2CH2- |
437 | NCH3 | 4-CH3O-C6H4 | CH3 | H | H | -CH2CH2CH2- |
438 | NCH3 | 3-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
439 | NCH3 | 4-Br-C6H4 | CH3 | H | H | -CH2CH2CH2- |
440 | NCH3 | 2-Cl-C6H4 | CH3 | H | H | -CH2CH2CH2- |
441 | NCH3 | C6H5 | CH3 | Cl | Cl | -CH2CH2CH2- |
442 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
443 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
444 | NCH3 | 4-C2H5-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
445 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | Cl | -CH2CH2CH2- |
446 | NCH3 | 4-CH3O-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
447 | NCH3 | 3-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
448 | NCH3 | 4-Br-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
449 | NCH3 | 2-Cl-C6H4 | CH3 | Cl | Cl | -CH2CH2CH2- |
450 | O | C6H5 | H | Cl | H | -CH2CH2CH2- |
451 | O | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
452 | O | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2- |
453 | O | 4-NO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
454 | O | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2- |
455 | O | 4-CN-C6H4 | H | Cl | H | -CH2CH2CH2- |
456 | O | 4-CH3CO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
457 | O | 4-CH3S-C6H4 | H | Cl | H | -CH2CH2CH2- |
458 | O | 4-CH3SO2-C6H4 | H | Cl | H | -CH2CH2CH2- |
459 | O | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
460 | O | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
461 | O | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2- |
462 | O | 2-Cl-4-F-C6H3 | H | Cl | H | -CH2CH2CH2- |
463 | O | 3-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
464 | O | 4-Br-C6H4 | H | Cl | H | -CH2CH2CH2- |
465 | O | C6H5 | Cl | Cl | H | -CH2CH2CH2- |
466 | O | 4-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
467 | O | 4-F-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
468 | O | 4-NO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
469 | O | 4-CF3-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
470 | O | 4-CN-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
471 | O | 4-CH3CO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
472 | O | 4-CH3S-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
473 | O | 4-CH3SO2-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
474 | O | 4-CF3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
475 | O | 2,4-2Cl-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
476 | O | 4-CH3O-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
477 | O | 2-Cl-4-F-C6H3 | Cl | Cl | H | -CH2CH2CH2- |
478 | O | 3-Cl-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
479 | O | 4-Br-C6H4 | Cl | Cl | H | -CH2CH2CH2- |
480 | O | C6H5 | CH3 | Cl | H | -CH2CH2CH2- |
481 | O | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
482 | O | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
483 | O | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
484 | O | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
485 | O | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
486 | O | 4-CH3CO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
487 | O | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
488 | O | 4-CH3SO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
489 | O | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
490 | O | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2- |
491 | O | 4-CH3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
492 | O | 3-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
493 | O | 4-Br-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
494 | O | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2- |
495 | NPh | CF3 | H | Cl | H | -CH2CH2CH2- |
496 | N(Ph-4-Cl) | C6H5 | H | Cl | H | -CH2CH2CH2- |
497 | NCH3 | CF3 | Ph | Cl | H | -CH2CH2CH2- |
498 | NCH3 | C6H5 | Ph | Cl | H | -CH2CH2CH2- |
499 | NCH3 | C6H5 | H | Cl | H | -CH2CH2- |
500 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2- |
501 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2- |
502 | NCH3 | 4-NO2-C6H4 | H | Cl | H | -CH2CH2- |
503 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2- |
504 | NCH3 | 4-CN-C6H4 | H | Cl | H | -CH2CH2- |
505 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2- |
506 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2- |
507 | NCH3 | 4-CH3CH2-C6H4 | H | Cl | H | -CH2CH2- |
508 | NCH3 | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2- |
509 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2- |
510 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2- |
511 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2- |
512 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2- |
513 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2- |
514 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2- |
515 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2- |
516 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2- |
517 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2- |
518 | NCH3 | 4-CH3CH2-C6H4 | CH3 | Cl | H | -CH2CH2- |
519 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2- |
520 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2- |
521 | NCH3 | C6H5 | H | Cl | H | -CH2CH2CH2CH2- |
522 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
523 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
524 | NCH3 | 4-NO2-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
525 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
526 | NCH3 | 4-CN-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
527 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
528 | NCH3 | 4-CH3O-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
529 | NCH3 | 4-CH3CH2-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
530 | NCH3 | 4-CF3O-C6H4 | H | Cl | H | -CH2CH2CH2CH2- |
531 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2CH2- |
532 | NCH3 | C6H5 | CH3 | Cl | H | -CH2CH2CH2CH2- |
533 | NCH3 | 4-Cl-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
534 | NCH3 | 4-F-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
535 | NCH3 | 4-NO2-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
536 | NCH3 | 4-CF3-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
537 | NCH3 | 4-CN-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
538 | NCH3 | 4-CH3-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
539 | NCH3 | 4-CH3S-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
540 | NCH3 | 4-CH3CH2-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
541 | NCH3 | 4-CF3O-C6H4 | CH3 | Cl | H | -CH2CH2CH2CH2- |
542 | NCH3 | 2,4-2Cl-C6H3 | CH3 | Cl | H | -CH2CH2CH2CH2- |
表12
编号 | X | R1 | R2 | R4 | R5 | Q |
543 | NPh | CF3 | H | Cl | H | -CH2CH2CH2- |
544 | N(Ph-4-Cl) | CH3 | H | Cl | H | -CH2CH2CH2- |
545 | NPh | H | H | Cl | H | -CH2CH2CH2- |
546 | N(Ph-4-Cl) | H | H | Cl | H | -CH2CH2CH2- |
547 | N(Ph-4-CF3) | H | H | Cl | H | -CH2CH2CH2- |
548 | N(Ph-2-CH3-4-Cl) | H | H | Cl | H | -CH2CH2CH2- |
549 | NPh | CO2C2H5 | H | Cl | H | -CH2CH2CH2- |
550 | N(Ph-4-Cl) | CO2C2H5 | H | Cl | H | -CH2CH2CH2- |
551 | N(Ph-2-CH3-4-Cl) | CO2C2H5 | H | Cl | H | -CH2CH2CH2- |
552 | N(Ph-2-CH3) | H | H | Cl | H | -CH2CH2CH2- |
553 | N(Ph-2-CH3) | CO2C2H5 | H | Cl | H | -CH2CH2CH2- |
554 | N(Ph-4-CH3) | H | H | Cl | H | -CH2CH2CH2- |
555 | N(Ph-2-Cl) | H | H | Cl | H | -CH2CH2CH2- |
556 | N(Ph-4-OCH3) | H | H | Cl | H | -CH2CH2CH2- |
557 | N(Ph-2,4-2Cl) | H | H | Cl | H | -CH2CH2CH2- |
558 | N(Ph-4-F) | H | H | Cl | H | -CH2CH2CH2- |
559 | NCH3 | C6H5 | H | Cl | H | -CH2CH2CH2- |
560 | NCH3 | 4-Cl-C6H4 | H | Cl | H | -CH2CH2CH2- |
561 | NCH3 | 4-F-C6H4 | H | Cl | H | -CH2CH2CH2- |
562 | NCH3 | 4-CH3-C6H4 | H | Cl | H | -CH2CH2CH2- |
563 | NCH3 | 4-CF3-C6H4 | H | Cl | H | -CH2CH2CH2- |
564 | NCH3 | 2,4-2Cl-C6H3 | H | Cl | H | -CH2CH2CH2- |
本发明的通式(I)所代表的化合物可以由通式(II)所示的含羟基的吡唑或异恶唑类化合物与通式(IV)所示的卤代丙烯类化合物在碱性条件下缩合制得,或者可以由通式(III)所示的吡唑或异恶唑类化合物与通式(V)所示的含羟基的卤代丙烯类化合物在碱性条件下缩合制得:
通式(III)、(IV)中,L是离去基团,选自氯或溴;其他各基团的定义同上。
通式(IV)、(V)所示的化合物可以由已知方法制得,具体参见CN1860874、US20030073847和WO9727173等。
反应在适宜的溶剂中进行,适宜的溶剂可选自如四氢呋喃、乙腈、甲苯、二甲苯、苯、N,N-二甲基甲酰胺、二甲亚砜、丙酮或丁酮等。
适宜的碱可选自如氢氧化钾、氢氧化钠、碳酸钠、碳酸钾、碳酸氢钠、三乙胺、吡啶、甲醇钠、乙醇钠、氢化钠、叔丁醇钾或叔丁醇钠等。
反应温度可在室温至溶剂沸点温度之间,通常为20~100℃。
反应时间为30分钟至20小时,通常1~10小时。
中间体(II)可购得,或者按照已知方法制备。其中:当五元杂环的3-位或5-位为羟基时,由中间体(VI)与(取代的)肼、羟胺缩合制得,参见:WO2005080344A1,Synlett 2004,5,795-798,J.Chem.Soc.,Perkin Trans.2,1987,969-975等。当五元杂环的4-位为羟基时,可由中间体(VI)酯解后与胺类化合物合环制得,参见OrganicPreparation and Procedures International,2002,34(1):98-102。通式(III)可由通式(II)卤化得到。
本发明的通式(I)化合物对农业、民用和动物技术领域中有害昆虫的成虫、幼虫和卵都显示出高杀虫活性。部分化合物表现出较好的杀菌活性。因此,本发明还包括通式(I)化合物在农业和其他领域中用作杀虫剂和/或杀菌剂的应用。
尤其是,通式(I)化合物对下列科和目的重要害虫有活性:鳞翅目害虫,如二化螟、稻纵卷叶螟、玉米螟、烟叶蛾、小食心虫、小菜蛾、甜菜夜蛾、斜纹夜蛾等。特别是对小菜蛾、甜菜夜蛾活性更好,在很低的剂量下就可以获得很好的效果。本发明对同翅目的害虫如蚜虫等也具有很高的活性。因此本发明的通式(I)化合物优选在农业和其他领域中用于防治鳞翅目和同翅目害虫的应用。同时,本发明的部分化合物还具有很好的杀菌活性,可用于防治水稻稻瘟病、番茄晚疫病、蔬菜灰霉病、小麦白粉病、黄瓜霜霉病、炭疽病等,特别是对水稻稻瘟病、黄瓜霜霉病、炭疽病有很好的活性。
同时,通式(I)化合物对许多有益的昆虫和螨虫、哺乳动物、鱼、鸟具有低毒性,而且没有植物毒性。
由于良好的性能,上述化合物可有利地用于保护农业和园艺业重要的作物、家畜和种畜,以及人类常去的环境免于有害昆虫和真菌的伤害。
为获得理想效果,化合物的用量因各种因素而改变,例如所用化合物、被保护的作物、有害生物的类型、感染程度、气候条件、施药方法、采用的剂型。
每公顷10克-1000克的化合物剂量能提供充分的防治。
本发明的另一目的还涉及通过施用通式(I)化合物,防治农业和园艺业重要的作物和/或家畜和种畜和/或人类常去的环境中的昆虫和/或植物致病性真菌的方法。尤其是,化合物的用量在每公顷10克-1000克内变化。
为了实际应用于农业,使用含一种或多种通式(I)化合物的组合物通常是有益的。
因此,本发明的另一目的涉及含一种或多种通式(I)化合物作为活性成分的杀虫和/或杀菌组合物,组合物中活性成分的重量百分含量为0.1-99%。
组合物的使用形式可以是干粉、可湿性粉剂、乳油、微乳剂、糊剂、颗粒剂、溶液、悬浮剂等:组合物类型的选择取决于具体的应用。
组合物是以已知方法制备的,例如任选在表面活性剂的存在下,通过用溶剂介质和/或固体稀释剂稀释或溶解活性物质。
可用的固体稀释剂或载体是例如:二氧化硅、高岭土、膨润土、滑石、硅藻土、白云石、碳酸钙、氧化镁、白垩、粘土、合成硅酸盐、硅镁土、海泡石等。
除水以外,可用的液体稀释剂还包括如芳族有机溶剂(二甲苯或烷基苯的混合物、氯苯等),石蜡(石油馏分),醇类(甲醇、丙醇、丁醇、辛醇、甘油),酯类(乙酸乙酯、乙酸异丁酯等),酮类(环己酮、丙酮、苯乙酮、异佛尔酮、乙基戊基酮等),酰胺类(N,N-二甲基甲酰胺、N-甲基吡咯烷酮等)。
可用的表面活性剂是烷基磺酸盐、烷基芳基磺酸盐、聚氧乙烯烷基酚、山梨醇的聚氧乙烯酯、木质素磺酸盐等的钠、钙、三乙基胺或三乙醇胺盐。
组合物还可含特殊的添加剂用于特定的目的,例如含有粘合剂如阿拉伯胶、聚乙烯醇、聚乙烯吡咯烷酮等。
上述组合物中活性成分的浓度可根据活性成分、使用目的、环境条件和采用的制剂类型而在宽范围内改变。活性成分的浓度范围通常为0.5-90%,优选5-60%。
如果需要,可以向组合物中添加能与通式(I)化合物兼容的其他活性成分,例如其他杀螨剂/杀虫剂、杀真菌剂、植物生长调节剂、抗生素、除草剂、肥料。
几种常见剂型的配制方法举例如下:
悬浮剂的配制:常用配方中活性组分含量为5-35%。以水为介质,将原药、分散剂、助悬剂和抗冻剂等加入砂磨机中,进行研磨,制成悬浮剂。
水乳剂的配制:将原药、溶剂和乳化剂加在一起,使溶解成均匀油相。将水、抗冻剂等混合一起,成为均一水相。在高速搅拌下,将水相加入到油相或将油相加入到水相,形成分散性良好的水乳剂。本发明的水乳剂活性组分含量一般为5%-15%。为制备浓乳剂,本发明的化合物可溶解于一种或数种混合溶剂,再加入乳化剂来增强化合物在水中的分散效果。
可湿性粉剂的配制:按配方要求,将原药、各种表面活性剂及固体稀释剂等充分混合,经超细粉碎机粉碎后,即得到预定含量(例如10-60%)的可湿性粉剂产品。为制备适于喷洒用的可湿性粉剂,本发明的化合物可以和研细的固体粉末如粘土、无机硅酸盐、碳酸盐以及润湿剂、粘合剂和/或分散剂组成混合物。
水分散性粒剂的配制:将原药和粉状固体稀释剂、润湿展着剂及粘合剂等进行混合粉碎,再加水捏合后,加入装有一定规格筛网的造粒机中进行造粒,然后再经干燥、筛分(按筛网范围)。也可将原药、分散剂、崩解剂和润湿剂及固体稀释剂加入砂磨机中,以水为介质研磨,制成悬浮剂,然后进行喷雾干燥造粒,通常配制含量为20-30%颗粒状产品。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非仅限于这些例子。
合成实施例
实例1:中间体的制备
向4.10克(18.5毫摩尔)4-(3,3-二氯烯丙氧基)苯酚的30毫升甲苯溶液中加入4滴(0.1毫升)二丁胺,于65-70℃下缓慢滴入0.95-3倍(摩尔)的磺酰氯的甲苯溶液,约2小时滴完,继续反应1-2小时,TLC监测反应完毕后,加入饱和碳酸氢钠溶液,分出甲苯层,水层用甲苯萃取,有机层合并,干燥,脱溶,柱层析得中间体。
实例2:中间体IV-1的制备
向20毫升N,N-二甲基甲酰胺(DMF)中加入4.2克1,3-二溴丙烷、2.9克无水碳酸钾,向其中滴加溶有3.8克2,6-二氯-4-(3′,3′-二氯)烯丙氧基苯酚的10毫升DMF溶液,控制温度在15℃左右,在此温度下反应1小时,TLC监测反应完毕后,向反应瓶中倒入50毫升饱和食盐水,用60毫升乙酸乙酯分三次进行萃取,干燥,脱溶,柱层析得4.35克中间体IV-1。
实例3:化合物2的制备
取0.22克II-1(自制,按照WO2005080344A1提供的方法制备)、0.23克无水碳酸钾于100毫升反应瓶中,加入40毫升N,N-二甲基甲酰胺(DMF),搅拌下加入0.45克IV-1,升温至35℃搅拌反应3小时。TLC监测反应完毕后,减压脱溶后,向反应瓶中倒入50毫升饱和食盐水,用60毫升乙酸乙酯分三次进行萃取,干燥,脱溶,柱层析得产品0.37克,即化合物2。
实例4:化合物269的制备
取0.18克II-2(自制,按照J.Chem.Soc.,Perkin Trans.2,1987,969-975提供的方法制备)、0.20克无水碳酸钾于100毫升反应瓶中,加入40毫升N,N-二甲基甲酰胺(DMF),搅拌下加入0.40克IV-1,升温至35℃搅拌反应3小时。TLC监测反应完毕后,减压脱溶后,向反应瓶中倒入50毫升饱和食盐水,用60毫升乙酸乙酯分三次进行萃取,干燥,脱溶,柱层析得产品0.33克,即化合物269。
实例5:化合物367的制备
取0.24克II-3(自制,按照J.Chem.Soc.,Perkin Trans.2,1987,969-975提供的方法制备)、0.27克无水碳酸钾于100毫升反应瓶中,加入40毫升N,N-二甲基甲酰胺(DMF),搅拌下加入0.49克IV-1,升温至35℃搅拌反应3小时。TLC监测反应完毕后,减压脱溶后,向反应瓶中倒入50毫升饱和食盐水,用60毫升乙酸乙酯分三次进行萃取,干燥,脱溶,柱层析得产品0.30克,即化合物367。
实例6:化合物546的制备
取0.25克II-4(自制,按照Organic Preparation and Procedures International,2002,34(1):98-102提供的方法制备)、0.28克无水碳酸钾于100毫升反应瓶中,加入40毫升N,N-二甲基甲酰胺(DMF),搅拌下加入0.52克IV-1,升温至35℃搅拌反应3小时。TLC监测反应完毕后,减压脱溶后,向反应瓶中倒入50毫升饱和食盐水,用60毫升乙酸乙酯分三次进行萃取,干燥,脱溶,柱层析得产品0.35克,即化合物546。
通式(I)的其他化合物可以用本发明提供的制备方法制得。
部分化合物熔点和核磁数据(1HNMR,300MHz,内标TMS,溶剂CDCl3)如下:
化合物1:油状物。δppm 7.75(m,2H),7.38(m,2H),7.28(m,1H),6.85(s,2H),6.11(t,1H),5.89(s,1H),4.58(d,2H),4.42(t,2H),4.15(t,2H),3.71(s,3H),2.32(m,2H)。
化合物2:熔点68-70℃。δppm 7.68(m,2H),7.33(m,2H),6.85(s,2H),6.11(t,1H),5.85(s,1H),4.58(d,2H),4.41(t,2H),4.15(t,2H),3.70(s,3H),2.32(m,2H)。
化合物8:油状物。δppm 7.67(m,2H),7.27(m,2H),6.84(s,2H),6.12(t,1H),5.84(s,1H),4.59(d,2H),4.40(t,2H),4.14(t,2H),3.69(s,3H),2.50(s,3H),2.32(m,2H)。
化合物13:熔点78-80℃。δppm 7.67(m,2H),6.91(m,4H),6.11(t,1H),5.81(s,1H),4.58(d,2H),4.40(t,2H),4.15(t,2H),3.83(s,3H),3.69(s,3H),2.32(m,2H)。
化合物16:油状物。δppm 7.64(m,2H),7.50(m,2H),6.85(s,2H),6.11(t,1H),5.86(s,1H),4.58(d,2H),4.41(t,2H),4.14(t,2H),3.70(s,3H),2.32(m,2H)。
化合物21:油状物。δppm 7.78(m,1H),7.42(m,1H),7.23(m,2H),6.84(s,2H),6.11(m,2H),4.58(d,2H),4.42(t,2H),4.16(t,2H),3.72(s,3H),2.33(m,2H)。
化合物76:油状物。δ7.63(d,2H),7.41(t,2H),7.32(t,1H),6.83(s,2H),6.10(t,1H),4.58(d,2H),4.40(t,2H),4.18(t,2H),3.76(s,3H),2.31(m,2H),2.17(s,3H)。
化合物130:油状物。δ7.70(m,2H),7.34(m,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.42(t,2H),4.15(t,2H),4.04(m,2H),2.32(m,2H),1.37(m,3H)。
化合物148:油状物。δ7.68(d,2H),7.33(d,2H),7.08(s,1H),6.39(t,1H),6.10(s,1H),4.77(d,2H),4.39(t,2H),4.24(t,2H),3.64(s,3H),2.34(m,2H)。
化合物166:油状物。δ7.55(m,2H),7.35(m,2H),7.25(m,1H),7.02(s,1H),6.35(t,1H),4.76(d,2H),4.35(t,2H),4.18(t,2H),3.69(s,3H),2.30(m,2H),2.14(s,3H)。
化合物225:熔点117-119℃。δ7.72(d,2H),7.39(d,2H),7.10(s,2H),6.41(t,1H),6.17(s,1H),4.66(d,2H),4.44(t,2H),4.31(t,2H),3.59(s,3H)。
化合物235:油状物。δ7.58(d,2H),7.39(t,2H),7.28(t,1H),7.11(s,2H),6.38(t,1H),4.66(d,2H),4.44(t,2H),4.23(t,2H),3.71(s,3H),2.14(s,3H)。
化合物247:油状物。δ7.67(d,2H),7.31(d,2H),6.96(s,2H),6.27(t,1H),5.96(s,1H),4.63(d,2H),4.20(t,2H),3.99(t,2H),3.63(s,3H),2.02(m,4H)。
化合物248:油状物。δ7.68(d,2H),7.45(d,2H),7.33(d,2H),7.01(s,1H),6.33(t,1),5.71(s,1H),4.64(d,2H),3.97(t,2H),3.68(t,2H),3.56(s,3H),1.94(m,4H)。
化合物257:油状物。δ7.56(d,2H),7.34(t,2H),7.22(t,1H),6.93(s,2H),6.22(t,1H),4.62(d,2H),4.16(t,2H),4.01(t,2H),3.69(s,3H),2.13(s,3H),2.04(s,4H)。
化合物268:油状物。δ7.43(m,5H),6.84(s,2H),6.15(t,1H),5.68(s,1H),4.60(d,2H),4.43(t,2H),4.18(t,2H),3.77(s,3H),2.32(m,2H)。
化合物269:熔点63-64℃。δ7.46(d,2H),7.35(d,2H),6.84(s,2H),6.11(t,1H),5.77(s,1H),4.58(d,2H),4.50(t,2H),4.15(t,2H),3.81(s,3H),2.32(m,2H)。
化合物350:油状物。δppm 7.49(m,3H),7.45(m,2H),6.96(s,1H),6.92(s,1H),4.48(m,2H),4.17(m,2H),3.64(s,3H),2.31(m,2H),1.88(s,3H),1.25(s,3H)。
化合物352:油状物。δppm 7.30(m,2H),7.18(m,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.49(t,2H),4.17(t,2H),3.60(s,3H),2.32(m,2H),1.85(s,3H)。
化合物356:油状物。δppm 7.22(m,2H),6.98(m,2H),6.84(s,2H),6.11(t,1H),4.58(d,2H),4.46(t,2H),4.17(t,2H),4.06(m,2H),3.42(s,3H),2.32(m,2H),1.86(s,3H),1.45(m,3H)。
化合物360:油状物。δppm 7.52(m,1H),7.33(m,1H),7.18(m,1H),6.82(s,2H),6.10(t,1H),4.56(d,2H),4.45(t,2H),4.15(t,2H),3.47(s,3H),2.31(m,2H),1.74(s,3H)。
化合物361:油状物。δppm 7.55(m,1H),7.41(m,1H),7.16(m,1H),6.84(s,2H),6.11(t,1H),4.58(d,2H),4.49(t,2H),4.17(t,2H),3.62(s,3H),2.32(m,2H),1.86(s,3H)。
化合物363:油状物。δppm 7.25(m,2H),6.98(m,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.47(t,2H),4.17(t,2H),3.86(s,3H),3.61(s,3H),2.32(m,2H),1.86(s,3H)。
化合物367:油状物。δppm 7.28(d,2H),7.21(d,2H),6.84(s,2H),6.12(t,1H),4.60(d,2H),4.47(t,2H),4.17(m,2H),3.61(s,3H),2.42(s,3H),2.32(t,2H),1.86(s,3H)。
化合物368:油状物。δppm 7.21-7.31(m,4H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.47(t,2H),4.17(t,2H),3.62(s,3H),2.71(m,2H),2.32(m,2H),1.87(s,3H),1.28(t,3H)。
化合物376:油状物。δppm 7.12(s,1H),7.06(m,2H),6.84(s,2H),6.12(t,1H),4.57(d,2H),4.47(t,2H),4.19(t,2H),3.43(s,3H),2.38(s,3H),2.30(t,2H),2.10(s,3H),1.73(s,3H)。
化合物377:油状物。δppm 7.24(m,1H),7.07(m,2H),6.84(s,2H),6.11(t,1H),4.58(d,2H),4.49(t,2H),4.17(t,2H),3.62(s,3H),2.34(s,6H),2.32(m,2H),1.86(s,3H)。
化合物378:油状物。δppm 7.17(m,2H),6.96(s,1H),6.84(s,2H),6.10(t,1H),4.57(d,2H),4.48(t,2H),4.18(t,2H),3.43(s,3H),2.34(s,3H),2.32(m,2H),2.08(s,3H),1.73(s,3H)。
化合物387:油状物。δppm 7.31(d,2H),7.23(d,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.48(t,2H),4.17(t,2H),3.63(s,3H),2.93(m,1H),2.32(m,2H),1.87(s,3H),1.31(s,3H),1.28(s,3H)。
化合物389:油状物。δppm 7.46(m,2H),7.25(m,2H),6.84(s,2H),6.12(t,1H),4.58(d,2H),4.46(t,2H),4.18(t,2H),3.62(s,3H),2.31(m,2H),1.88(s,3H),1.36(s,9H)。
化合物423:油状物。δ7.42(d,2H),7.34(d,2H),6.88(s,1H),6.19(t,1H),5.73(s,1H),4.68(d,2H),4.39(t,2H),4.15(t,2H),3.71(s,3H),2.31(m,2H)。
化合物443:油状物。δ7.30(m,3H),7.21(d,2H),6.31(t,1H),4.76(d,2H),4.35(t,2H),4.11(t,2H),3.55(s,3H),2.40(s,3H),1.80(s,3H)。
化合物444:油状物。δ7.31(d,2H),7.24(d,2H),7.16(s,1H),6.29(t,1H),4.76(d,2H),4.34(t,2H),4.11(t,2H),3.55(s,3H),2.68(m,2H),2.23(q,2H),1.80(s,3H),1.26(t,3H)。
化合物499:油状物。δ7.44(m,3H),7.32(d,2H),6.96(s,2H),6.27(t,1H),4.63(d,2H),4.45(t,2H),4.28(t,2H),3.57(s,3H),1.82(s,3H)。
化合物500:熔点82-83℃。δ7.48(s,4H),7.03(s,2H),6.35(t,1H),5.78(s,1H),4.65(d,2H),4.40(t,2H),4.24(t,2H),3.69(s,3H)。
化合物516:油状物。δppm 7.27(m,2H),7.18(m,2H),6.85(s,2H),6.12(t,1H),4.59(m,4H),4.36(m,2H),3.60(s,3H),2.41(s,3H),1.87(s,3H)。
化合物518(DMSO):油状物。δppm 7.30(m,2H),7.23(m,2H),7.05(s,2H),6.38(m,1H),4.65(m,2H),4.45(m,2H),4.27(m,2H),3.55(s,3H),2.68(m,2H),1.80(s,3H),1.27(m,3H)。
化合物522:油状物。δ7.43(s,4H),6.94(s,2H),6.24(t,1H),5.65(s,1H),4.63(d,2H),4.17(t,2H),3.98(t,2H),3.69(s,3H),1.96(s,4H)。
化合物532:油状物。δ7.45(m,3H),7.31(d,2H),6.95(s,2H),6.27(t,1H),4.63(d,2H),4.19(t,2H),3.99(t,2H),3.56(s,3H),1.96(s,4H),1.82(s,3H)。
化合物538(DMSO):油状物。δppm 7.26(m,2H),7.19(m,2H),7.03(s,2H),6.36(m,1H),4.64(m,2H),4.17(m,2H),3.98(m,2H),3.53(s,3H),2.38(s,3H),1.94(m,4H),1.79(s,3H)。
化合物540:油状物。δppm 7.27(m,4H),6.85(s,2H),6.13(t,1H),4.58(m,2H),4.29(m,2H),4.04(m,2H),3.62(s,3H),2.71(m,2H),2.03(m,2H),1.87(s,3H),1.29(t,3H)。
化合物546:油状物。δppm 7.58(s,1H),7.56(d,2H),7.50(s,1H),7.38(d,2H),6.84(s,2H),6.10(t,1H),4.59(d,2H),4.24(t,2H),4.14(t,2H),2.27(q,2H)。
化合物547:油状物。δppm 7.64(d,2H),7.58(s,1H),7.50(s,1H),7.27(d,2H),6.84(s,2H),6.10(t,1H),4.59(d,2H),4.24(t,2H),4.14(t,2H),2.28(q,2H).
化合物550:油状物。δppm 7.76(d,2H),7.65(s,1H),7.29(d,2H),6.38(s,2H),6.10(t,1H),4.56(d,2H),4.44(q,2H),4.33(t,2H),4.19(t,2H),2.35(q,2H),1.41(t,3H)。
化合物551:油状物。δppm 7.32(s,1H),7.29(d,2H),7.28(s,1H),7.26(d,2H),6.83(s,2H),6.11(t,1H),4.59(d,2H),4.42(q,2H),4.29(t,2H),4.18(t,2H),2.35(q,2H),2.22(s,3H),1.41(t,3H)。
制剂实施例(各组分加入量均为重量百分含量,活性化合物折百后计量加入)
实例7:30%可湿性粉剂
将化合物2及其他组分充分混合,经超细粉碎机粉碎后,即得到30%的可湿性粉剂产品。
实例8:40%浓悬浮剂
将化合物367及其他组分充分混合,由此得到的浓悬浮剂,用水稀释所得悬浮剂可得到任何所需浓度的稀释液。
实例9:60%水分散性粒剂
将化合物367及其他组分混合粉碎,再加水捏合后,加入10-100目筛网的
造粒机中进行造粒,然后再经干燥、筛分(按筛网范围)。
生物活性测定实施例
实例10:杀虫杀螨活性测定
用本发明化合物对几种昆虫和螨类进行了杀虫活性测定试验。测定的方法如下:
待测化合物用丙酮/甲醇(1∶1)的混合溶剂溶解后,用含有0.1%(wt)吐温80的水稀释至所需的浓度。
以小菜蛾为靶标,采用airbrush喷雾法进行杀虫活性测定。
对于小菜蛾的测定:将甘蓝叶片用打孔器打成直径1cm的叶碟,airbrush喷雾处理的压力为10psi(约合0.7kg/cm2),每叶碟正反面喷雾,喷液量为0.5ml。阴干后每处理接入10头2龄试虫,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,72小时后调查存活虫数,计算死亡率。
部分测试结果如下:
药液浓度为100mg/L时,对小菜蛾2龄幼虫致死率达到100%的化合物有1、2、8、11、13、16、17、18、24、26、38、76、77、86、92、225、247、248、257、268、269、278、280、283、284、293、306、352、356、360、361、363、367、368、377、387、389、500、522、532、538、546。在此浓度下,对照药剂pyridalyl的致死率亦为100%。
药液浓度为25mg/L时,对小菜蛾2龄幼虫致死率达到100%的化合物有2、225、247、248、268、269、352、367、377、387。在此浓度下,对照药剂pyridalyl的致死率亦为100%。
药液浓度为6.25mg/L时,对小菜蛾2龄幼虫致死率达到80%以上的化合物有2、248、367、377、387,致死率达到90%以上的化合物有2、367。在此浓度下,对照药剂pyridalyl的致死率为65%。
实例11杀菌活性测定
用本发明化合物对植物的各种菌病害进行了试验。试验的方法如下:
活体保护活性测定:采用活体盆栽测定方法。待测化合物原药用少量丙酮溶解,用含有0.1%(wt)吐温80的水稀释至所需的浓度。喷雾施药到植物试材上,24小时后进行病害接种。接种后,将植物放在恒温恒湿培养箱中,使感染继续,待对照充分发病后(通常为一周时间)进行评估调查。
部分测试结果如下:
活体保护活性测定:药液浓度为400ppm时,化合物2等对小麦白粉病防效在70%以上。
Claims (5)
1.一种具有含氮五元杂环的醚类化合物,如通式(I)所示:
式中:
R3选自氯;
Y1、Y2选自氯;
A1、A2选自O;
A2与杂环的连接位置选自3、4或5位;当A2与杂环5位连接时,则R1在3位,R2在4位,结构式如I-1所示;当A2与杂环3位连接时,则R1在5位,R2在4位,结构式如I-2所示;当A2与杂环4位连接时,则R1在3位,R2在5位,结构式如I-3所示;
通式(I-3)中
R1选自氢、CO2R6或C1-C6烷基;
R2选自氢、氟、氯、溴或C1-C6烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基或R7;
R6选自氢或C1-C4烷基;
R7选自苯基,或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、CN、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基或C1-C6烷硫基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-;
通式(I-1)或通式(I-2)中
R1选自苯基,或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基或C1-C4烷硫基;
R2选自氢、氯或C1-C4烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基;
R6选自氢或C1-C4烷基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-。
2.根据权利要求1所述的化合物,其特征在于:通式(I-3)中
R1选自氢、CO2R6或C1-C4烷基;
R2选自氢、氟、氯、溴或C1-C4烷基;
R4、R5可相同或不同,分别选自氢或氯;
X选自NR8;
R8选自C1-C4烷基、苯基、或者被1-3个独立选自以下基团进一步取代的苯基:氟、氯、溴、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R6选自氢或C1-C4烷基;
Q选自-CH2CH2-、-CH2CH2CH2-或-CH2CH2CH2CH2-。
3.一种按照权利要求1所述的通式(I)化合物在农业或其他领域中防治害虫的应用。
4.一种按照权利要求1所述的通式(I)化合物在农业或其他领域中防治病菌的应用。
5.一种杀虫杀菌组合物,其特征在于:含有如权利要求1所述的通式(I)化合物作为活性组分,组合物中活性组分的重量百分含量为0.1-99%。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009801381313A CN102216294B (zh) | 2008-11-28 | 2009-11-25 | 具有含氮五元杂环的醚类化合物及其应用 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200810227711.7 | 2008-11-28 | ||
CN2008102277117A CN101747276B (zh) | 2008-11-28 | 2008-11-28 | 具有含氮五元杂环的醚类化合物及其应用 |
CN2009801381313A CN102216294B (zh) | 2008-11-28 | 2009-11-25 | 具有含氮五元杂环的醚类化合物及其应用 |
PCT/CN2009/075131 WO2010060379A1 (zh) | 2008-11-28 | 2009-11-25 | 具有含氮五元杂环的醚类化合物及其应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102216294A CN102216294A (zh) | 2011-10-12 |
CN102216294B true CN102216294B (zh) | 2013-08-28 |
Family
ID=42225266
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008102277117A Active CN101747276B (zh) | 2008-11-28 | 2008-11-28 | 具有含氮五元杂环的醚类化合物及其应用 |
CN2009801381313A Active CN102216294B (zh) | 2008-11-28 | 2009-11-25 | 具有含氮五元杂环的醚类化合物及其应用 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2008102277117A Active CN101747276B (zh) | 2008-11-28 | 2008-11-28 | 具有含氮五元杂环的醚类化合物及其应用 |
Country Status (4)
Country | Link |
---|---|
US (1) | US8222280B2 (zh) |
CN (2) | CN101747276B (zh) |
BR (1) | BRPI0922073B1 (zh) |
WO (1) | WO2010060379A1 (zh) |
Families Citing this family (152)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101747276B (zh) | 2008-11-28 | 2011-09-07 | 中国中化股份有限公司 | 具有含氮五元杂环的醚类化合物及其应用 |
EP2635278B1 (en) | 2010-11-03 | 2019-12-11 | Dow AgroSciences LLC | Pesticidal compositions and processes related thereto |
MX355431B (es) | 2011-10-26 | 2018-04-18 | Dow Agrosciences Llc | Composiciones plaguicidas y procesos relacionados con dichas composiciones. |
US9376376B2 (en) | 2012-03-14 | 2016-06-28 | Sinochem Corporation | Substitute diphenylamine compounds use thereof as antitumor agents |
US9282739B2 (en) | 2012-04-27 | 2016-03-15 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
US9708288B2 (en) | 2012-04-27 | 2017-07-18 | Dow Agrosciences Llc | Pesticidal compositions and processes related thereto |
JP6463670B2 (ja) | 2012-04-27 | 2019-02-06 | ダウ アグロサイエンシィズ エルエルシー | 農薬組成物およびそれらに関する方法 |
JP2015532274A (ja) | 2012-10-01 | 2015-11-09 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 栽培植物へのn−チオ−アントラニルアミド化合物の使用 |
CN104768377A (zh) | 2012-10-01 | 2015-07-08 | 巴斯夫欧洲公司 | 包含邻氨基苯甲酰胺类化合物的农药活性混合物 |
AR094139A1 (es) | 2012-10-01 | 2015-07-15 | Basf Se | Mezclas activas como plaguicidas, que comprenden compuestos de antranilamida |
WO2014053407A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | N-thio-anthranilamide compounds and their use as pesticides |
WO2014053403A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling insecticide resistant insects |
WO2014053406A1 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of controlling ryanodine-modulator insecticide resistant insects |
WO2014053401A2 (en) | 2012-10-01 | 2014-04-10 | Basf Se | Method of improving plant health |
US20150313241A1 (en) | 2012-11-22 | 2015-11-05 | Basf Corporation | Pesticidal Mixtures |
WO2014079770A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079841A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
CN104902756B (zh) | 2012-11-22 | 2018-11-27 | 巴斯夫公司 | 农药混合物 |
EP2922395B1 (en) | 2012-11-22 | 2019-06-05 | BASF Corporation | Pesticidal mixtures |
WO2014079774A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079820A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Use of anthranilamide compounds for reducing insect-vectored viral infections |
WO2014079804A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079766A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079772A1 (en) | 2012-11-22 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079752A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
WO2014079813A1 (en) | 2012-11-23 | 2014-05-30 | Basf Se | Pesticidal mixtures |
JP2016501264A (ja) | 2012-12-14 | 2016-01-18 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 動物有害生物を防除するためのマロノニトリル化合物 |
US20150368236A1 (en) | 2012-12-27 | 2015-12-24 | Basf Se | 2-(pyridin-3-yl)-5-hetaryl-thiazole compounds carrying an imine or imine-derived substituent for combating invertebrate pests |
US20160050923A1 (en) | 2013-04-19 | 2016-02-25 | Basf Se | N-substituted acyl-imino-pyridine compounds and derivatives for combating animal pests |
BR112015031439A2 (pt) | 2013-06-21 | 2017-07-25 | Basf Se | métodos para o combate ou controle das pragas, para o tratamento, prevenção e proteção de culturas de soja, para o controle e proteção do material de propagação dos vegetais de soja, para o combate ou controle das pragas e utilização de um composto de fórmula i |
AR097138A1 (es) | 2013-07-15 | 2016-02-24 | Basf Se | Compuestos plaguicidas |
CA2922506A1 (en) | 2013-09-19 | 2015-03-26 | Basf Se | N-acylimino heterocyclic compounds |
WO2015055497A1 (en) | 2013-10-16 | 2015-04-23 | Basf Se | Substituted pesticidal pyrazole compounds |
EP3057431A4 (en) | 2013-10-17 | 2017-04-05 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
US9108946B2 (en) | 2013-10-17 | 2015-08-18 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
WO2015058024A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
CA2925954A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
US9102654B2 (en) | 2013-10-17 | 2015-08-11 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
WO2015058020A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
EP3057428A4 (en) | 2013-10-17 | 2017-05-17 | Dow AgroSciences LLC | Processes for the preparation of pesticidal compounds |
WO2015055757A1 (en) | 2013-10-18 | 2015-04-23 | Basf Se | Use of pesticidal active carboxamide derivative in soil and seed application and treatment methods |
AR098100A1 (es) | 2013-10-22 | 2016-05-04 | Dow Agrosciences Llc | Composiciones plaguicidas y los métodos relacionados |
US9491944B2 (en) | 2013-10-22 | 2016-11-15 | Dow Agrosciences Llc | Pesticidal compositions and related methods |
AU2014340413B2 (en) | 2013-10-22 | 2017-09-07 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
CN105792651A (zh) | 2013-10-22 | 2016-07-20 | 美国陶氏益农公司 | 杀虫组合物和与其相关的方法 |
NZ719776A (en) | 2013-10-22 | 2017-06-30 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
TW201519779A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法(十二) |
MX2016005310A (es) | 2013-10-22 | 2016-08-08 | Dow Agrosciences Llc | Composiciones pesticidas sinergicas y metodos relacionados. |
TW201519776A (zh) | 2013-10-22 | 2015-06-01 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法(八) |
AU2014340432B2 (en) | 2013-10-22 | 2017-09-07 | Dow Agrosciences Llc | Pesticidal compositions and related methods |
EP3060055A4 (en) | 2013-10-22 | 2017-03-29 | Dow AgroSciences LLC | Synergistic pesticidal compositions and related methods |
TW201517797A (zh) | 2013-10-22 | 2015-05-16 | Dow Agrosciences Llc | 協同性殺蟲組成物及相關方法(十一) |
AU2014340409B2 (en) | 2013-10-22 | 2017-09-07 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
US9144241B2 (en) | 2013-10-22 | 2015-09-29 | Dow Agrosciences Llc | Synergistic pesticidal compositions and related methods |
JP2016534068A (ja) | 2013-10-22 | 2016-11-04 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
RU2656888C2 (ru) | 2013-10-22 | 2018-06-07 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и связанные с ними способы |
JP2016535026A (ja) | 2013-10-22 | 2016-11-10 | ダウ アグロサイエンシィズ エルエルシー | 相乗的有害生物防除組成物および関連する方法 |
RU2656889C2 (ru) | 2013-10-22 | 2018-06-07 | ДАУ АГРОСАЙЕНСИЗ ЭлЭлСи | Пестицидные композиции и соответствующие способы |
US20160318897A1 (en) | 2013-12-18 | 2016-11-03 | Basf Se | Azole compounds carrying an imine-derived substituent |
EP3083581A1 (en) | 2013-12-18 | 2016-10-26 | Basf Se | N-substituted imino heterocyclic compounds |
WO2015104422A1 (en) | 2014-01-13 | 2015-07-16 | Basf Se | Dihydrothiophene compounds for controlling invertebrate pests |
WO2016018443A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
EP3174856A4 (en) | 2014-07-31 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
CA2954631A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
EP3183238A4 (en) | 2014-08-19 | 2018-01-10 | Dow AgroSciences LLC | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
WO2016039781A1 (en) | 2014-09-12 | 2016-03-17 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
EP3204390B1 (en) | 2014-10-06 | 2019-06-05 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
CN104326986B (zh) * | 2014-10-08 | 2016-05-04 | 南通大学 | 二氯丙烯基苯醚类化合物的制备方法及其应用 |
BR112017009513A2 (pt) | 2014-11-06 | 2018-02-06 | Basf Se | utilização de um composto heterobicíclico, utilização dos compostos i, compostos, composição agrícola ou veterinária, método para o combate ou controle de pragas, método para a proteção de culturas e sementes |
AU2015374118B2 (en) | 2014-12-29 | 2020-07-23 | The Trustees Of The University Of Pennsylvania | Small molecule inhibitors of lactate dehydrogenase and methods of use thereof |
AU2016214305B2 (en) | 2015-02-06 | 2020-10-08 | Basf Se | Pyrazole compounds as nitrification inhibitors |
CA3170386A1 (en) | 2015-02-11 | 2016-08-18 | Basf Se | Pesticidal mixture comprising a pyrazole compound, an insecticide and a fungicide |
CA2980505A1 (en) | 2015-04-07 | 2016-10-13 | Basf Agrochemical Products B.V. | Use of an insecticidal carboxamide compound against pests on cultivated plants |
AU2016260805A1 (en) | 2015-05-12 | 2017-11-23 | Basf Se | Thioether compounds as nitrification inhibitors |
WO2016198611A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino heterocyclic compounds |
WO2016198613A1 (en) | 2015-06-11 | 2016-12-15 | Basf Se | N-(thio)acylimino compounds |
WO2017016883A1 (en) | 2015-07-24 | 2017-02-02 | Basf Se | Process for preparation of cyclopentene compounds |
EP3356341B1 (en) | 2015-10-02 | 2020-04-01 | Basf Se | Imino compounds with a 2-chloropyrimidin-5-yl substituent as pest-control agents |
EP3383183B1 (en) | 2015-11-30 | 2020-05-27 | Basf Se | Compositions containing cis-jasmone and bacillus amyloliquefaciens |
EP3426660A1 (en) | 2016-03-09 | 2019-01-16 | Basf Se | Spirocyclic derivatives |
US20190082696A1 (en) | 2016-03-11 | 2019-03-21 | Basf Se | Method for controlling pests of plants |
UA123912C2 (uk) | 2016-04-01 | 2021-06-23 | Басф Се | Біциклічні сполуки |
US20190276376A1 (en) | 2016-05-18 | 2019-09-12 | Basf Se | Capsules comprising benzylpropargylethers for use as nitrification inhibitors |
EP3555050A1 (en) | 2016-12-16 | 2019-10-23 | Basf Se | Pesticidal compounds |
CN110325036B (zh) | 2016-12-29 | 2021-10-26 | 美国陶氏益农公司 | 用于制备杀虫化合物的方法 |
US10100033B2 (en) | 2016-12-29 | 2018-10-16 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
WO2018162312A1 (en) | 2017-03-10 | 2018-09-13 | Basf Se | Spirocyclic derivatives |
WO2018166855A1 (en) | 2017-03-16 | 2018-09-20 | Basf Se | Heterobicyclic substituted dihydroisoxazoles |
KR102596592B1 (ko) | 2017-03-28 | 2023-10-31 | 바스프 에스이 | 살충 화합물 |
AU2018241628B2 (en) | 2017-03-31 | 2022-03-17 | Basf Se | Pyrimidinium compounds and their mixtures for combating animal pests |
WO2018192793A1 (en) | 2017-04-20 | 2018-10-25 | Basf Se | Substituted rhodanine derivatives |
MX2019012813A (es) | 2017-04-26 | 2020-01-14 | Basf Se | Derivados de succinimida sustituida como plaguicidas. |
CA3059282A1 (en) | 2017-05-10 | 2018-11-15 | Basf Se | Bicyclic pesticidal compounds |
WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
CN110770235A (zh) | 2017-06-16 | 2020-02-07 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
EP3642203A1 (en) | 2017-06-19 | 2020-04-29 | Basf Se | Substituted pyrimidinium compounds and derivatives for combating animal pests |
WO2018234488A1 (en) | 2017-06-23 | 2018-12-27 | Basf Se | SUBSTITUTED CYCLOPROPYL DERIVATIVES |
WO2019042932A1 (en) | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
EP3453706A1 (en) | 2017-09-08 | 2019-03-13 | Basf Se | Pesticidal imidazole compounds |
BR112020006037A2 (pt) | 2017-10-13 | 2020-10-06 | Basf Se | compostos, misturas pesticidas, composição agroquímica, métodos para controlar pragas de invertebrados, para proteger plantas e para proteção de material de propagação de plantas, semente e uso de compostos de fórmula (i) |
CN109897031B (zh) * | 2017-12-11 | 2022-03-15 | 南京农业大学 | 一种含香豆素基团的苯并噻唑类衍生物及其制备方法与应用 |
WO2019121143A1 (en) | 2017-12-20 | 2019-06-27 | Basf Se | Substituted cyclopropyl derivatives |
UA127604C2 (uk) | 2017-12-21 | 2023-11-01 | Басф Се | Пестицидні сполуки |
BR112020012706A2 (pt) | 2018-01-09 | 2020-11-24 | Basf Se | uso de um composto de silietinil hetarila, composição para uso na redução de nitrificação, mistura agroquímica, métodos para reduzir a nitrificação e para tratamento de um fertilizante ou de uma composição |
WO2019137995A1 (en) | 2018-01-11 | 2019-07-18 | Basf Se | Novel pyridazine compounds for controlling invertebrate pests |
IL276745B2 (en) | 2018-02-28 | 2023-10-01 | Basf Se | Use of N-functional alkoxy pyrazole compounds as nitrification inhibitors |
WO2019166561A1 (en) | 2018-02-28 | 2019-09-06 | Basf Se | Use of alkoxypyrazoles as nitrification inhibitors |
EP3758491A1 (en) | 2018-02-28 | 2021-01-06 | Basf Se | Use of pyrazole propargyl ethers as nitrification inhibitors |
WO2019175712A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New uses for catechol molecules as inhibitors to glutathione s-transferase metabolic pathways |
WO2019175713A1 (en) | 2018-03-14 | 2019-09-19 | Basf Corporation | New catechol molecules and their use as inhibitors to p450 related metabolic pathways |
WO2019185413A1 (en) | 2018-03-27 | 2019-10-03 | Basf Se | Pesticidal substituted cyclopropyl derivatives |
WO2019219529A1 (en) | 2018-05-15 | 2019-11-21 | Basf Se | Mixtures comprising benzpyrimoxan and oxazosulfyl and uses and methods of applying them |
WO2019224092A1 (en) | 2018-05-22 | 2019-11-28 | Basf Se | Pesticidally active c15-derivatives of ginkgolides |
WO2020002472A1 (en) | 2018-06-28 | 2020-01-02 | Basf Se | Use of alkynylthiophenes as nitrification inhibitors |
WO2020020777A1 (en) | 2018-07-23 | 2020-01-30 | Basf Se | Use of substituted 2-thiazolines as nitrification inhibitors |
ES2969872T3 (es) | 2018-07-23 | 2024-05-23 | Basf Se | Uso de un compuesto de tiazolidina sustituida como inhibidor de la nitrificación |
EP3613736A1 (en) | 2018-08-22 | 2020-02-26 | Basf Se | Substituted glutarimide derivatives |
CN109293579A (zh) * | 2018-09-20 | 2019-02-01 | 浙江工业大学 | 偕二氟亚甲基串联的芳基-杂环化合物的合成方法 |
EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
CA3112042A1 (en) | 2018-09-28 | 2020-04-02 | Basf Se | Method of controlling pests by seed treatment application of a mesoionic compound or mixture thereof |
EP3643705A1 (en) | 2018-10-24 | 2020-04-29 | Basf Se | Pesticidal compounds |
EP3887357A1 (en) | 2018-11-28 | 2021-10-06 | Basf Se | Pesticidal compounds |
WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
WO2020126591A1 (en) | 2018-12-18 | 2020-06-25 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
EP3696177A1 (en) | 2019-02-12 | 2020-08-19 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
WO2020239517A1 (en) | 2019-05-29 | 2020-12-03 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
EP3766879A1 (en) | 2019-07-19 | 2021-01-20 | Basf Se | Pesticidal pyrazole derivatives |
CA3162521A1 (en) | 2019-12-23 | 2021-07-01 | Basf Se | Enzyme enhanced root uptake of agrochemical active compound |
US20230106291A1 (en) | 2020-02-28 | 2023-04-06 | BASF Agro B.V. | Methods and uses of a mixture comprising alpha-cypermethrin and dinotefuran for controlling invertebrate pests in t |
EP4143167B1 (en) | 2020-04-28 | 2024-05-15 | Basf Se | Pesticidal compounds |
EP3909950A1 (en) | 2020-05-13 | 2021-11-17 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
AR124796A1 (es) | 2021-02-02 | 2023-05-03 | Basf Se | Acción sinérgica de dcd y alcoxipirazoles como inhibidores de la nitrificación |
EP4043444A1 (en) | 2021-02-11 | 2022-08-17 | Basf Se | Substituted isoxazoline derivatives |
AR125955A1 (es) | 2021-05-21 | 2023-08-30 | Basf Se | Uso de un compuesto de alcoxi pirazol n-funcionalizado como inhibidor de nitrificación |
WO2022243521A1 (en) | 2021-05-21 | 2022-11-24 | Basf Se | Use of ethynylpyridine compounds as nitrification inhibitors |
WO2022268810A1 (en) | 2021-06-21 | 2022-12-29 | Basf Se | Metal-organic frameworks with pyrazole-based building blocks |
EP4119547A1 (en) | 2021-07-12 | 2023-01-18 | Basf Se | Triazole compounds for the control of invertebrate pests |
EP4140986A1 (en) | 2021-08-23 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4140995A1 (en) | 2021-08-27 | 2023-03-01 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4151631A1 (en) | 2021-09-20 | 2023-03-22 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP4194453A1 (en) | 2021-12-08 | 2023-06-14 | Basf Se | Pyrazine compounds for the control of invertebrate pests |
EP4198033A1 (en) | 2021-12-14 | 2023-06-21 | Basf Se | Heterocyclic compounds for the control of invertebrate pests |
EP4198023A1 (en) | 2021-12-16 | 2023-06-21 | Basf Se | Pesticidally active thiosemicarbazone compounds |
EP4238971A1 (en) | 2022-03-02 | 2023-09-06 | Basf Se | Substituted isoxazoline derivatives |
WO2023203066A1 (en) | 2022-04-21 | 2023-10-26 | Basf Se | Synergistic action as nitrification inhibitors of dcd oligomers with alkoxypyrazole and its oligomers |
WO2023208447A1 (en) | 2022-04-25 | 2023-11-02 | Basf Se | An emulsifiable concentrate having a (substituted) benzaldehyde-based solvent system |
WO2024028243A1 (en) | 2022-08-02 | 2024-02-08 | Basf Se | Pyrazolo pesticidal compounds |
EP4342885A1 (en) | 2022-09-20 | 2024-03-27 | Basf Se | N-(3-(aminomethyl)-phenyl)-5-(4-phenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-amine derivatives and similar compounds as pesticides |
EP4389210A1 (en) | 2022-12-21 | 2024-06-26 | Basf Se | Heteroaryl compounds for the control of invertebrate pests |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1167104A (zh) * | 1996-01-31 | 1997-12-10 | 住友化学工业株式会社 | 氟丙烯化合物,含有该化合物的杀虫剂以及制备过程中的中间体 |
CN1318535A (zh) * | 1994-10-14 | 2001-10-24 | 住友化学工业株式会社 | 二卤丙烯化合物,含有二卤丙烯化合物的杀虫剂/杀螨剂以及用于其生产的中间体 |
WO2005019147A2 (en) * | 2003-08-26 | 2005-03-03 | Syngenta Participations Ag | Pesticidally active phenol derivatives |
CN1761654A (zh) * | 2003-03-25 | 2006-04-19 | 住友化学株式会社 | 吡唑化合物 |
CN1914178A (zh) * | 2004-02-05 | 2007-02-14 | 住友化学株式会社 | 吡唑化合物及其在控制有害节肢动物害虫的组合物中的用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10155385A1 (de) | 2001-11-10 | 2003-05-28 | Bayer Cropscience Gmbh | Dihalogenpropen-Verbindungen, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel |
US7226925B2 (en) * | 2002-06-19 | 2007-06-05 | Biovitrum Ab | Compounds, their use and preparation |
TWI344340B (en) | 2004-02-05 | 2011-07-01 | Sumitomo Chemical Co | Pyrazole compounds and use thereof |
GB2434945B (en) * | 2006-01-31 | 2008-04-09 | Roke Manor Research | A method of filtering high data rate traffic |
CN101747276B (zh) | 2008-11-28 | 2011-09-07 | 中国中化股份有限公司 | 具有含氮五元杂环的醚类化合物及其应用 |
-
2008
- 2008-11-28 CN CN2008102277117A patent/CN101747276B/zh active Active
-
2009
- 2009-11-25 CN CN2009801381313A patent/CN102216294B/zh active Active
- 2009-11-25 WO PCT/CN2009/075131 patent/WO2010060379A1/zh active Application Filing
- 2009-11-25 BR BRPI0922073A patent/BRPI0922073B1/pt active IP Right Grant
- 2009-11-25 US US13/121,334 patent/US8222280B2/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1318535A (zh) * | 1994-10-14 | 2001-10-24 | 住友化学工业株式会社 | 二卤丙烯化合物,含有二卤丙烯化合物的杀虫剂/杀螨剂以及用于其生产的中间体 |
CN1167104A (zh) * | 1996-01-31 | 1997-12-10 | 住友化学工业株式会社 | 氟丙烯化合物,含有该化合物的杀虫剂以及制备过程中的中间体 |
CN1761654A (zh) * | 2003-03-25 | 2006-04-19 | 住友化学株式会社 | 吡唑化合物 |
WO2005019147A2 (en) * | 2003-08-26 | 2005-03-03 | Syngenta Participations Ag | Pesticidally active phenol derivatives |
CN1914178A (zh) * | 2004-02-05 | 2007-02-14 | 住友化学株式会社 | 吡唑化合物及其在控制有害节肢动物害虫的组合物中的用途 |
Also Published As
Publication number | Publication date |
---|---|
BRPI0922073A2 (pt) | 2015-08-11 |
US8222280B2 (en) | 2012-07-17 |
BRPI0922073B1 (pt) | 2018-09-25 |
CN102216294A (zh) | 2011-10-12 |
WO2010060379A1 (zh) | 2010-06-03 |
US20110178149A1 (en) | 2011-07-21 |
CN101747276A (zh) | 2010-06-23 |
CN101747276B (zh) | 2011-09-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102216294B (zh) | 具有含氮五元杂环的醚类化合物及其应用 | |
CN101747306B (zh) | 取代醚类化合物及其应用 | |
CN101668748B (zh) | 取代嘧啶醚类化合物及其应用 | |
CN100427481C (zh) | 一种芳基醚类化合物及其制备与应用 | |
CN102718701B (zh) | 芳氧基二卤丙烯醚类化合物与应用 | |
CN102336744B (zh) | 取代三唑啉酮醚类化合物及其作为杀菌、杀虫、杀螨剂的用途 | |
CN101875639B (zh) | 取代嘧啶醚类化合物及其应用 | |
CN102336743B (zh) | 取代三唑啉酮醚类化合物及其应用 | |
CN102336742A (zh) | 一种取代三唑啉酮醚类化合物及其应用 | |
CN101205187B (zh) | 取代芳基醚类化合物及其制备与应用 | |
CN102464612B (zh) | 含哌嗪氨基甲酸酯的二卤丙烯醚类化合物与应用 | |
CN102464621B (zh) | 含嘧啶环的醚类化合物及其应用 | |
CN102993189B (zh) | 一种含腙的三唑啉酮类化合物及其用途 | |
CN101921228A (zh) | 含哌嗪的二卤丙烯醚类化合物与应用 | |
CN101205202B (zh) | 取代苯基脲类化合物及其制备与应用 | |
CN102464622B (zh) | 取代嘧啶氨类化合物及其应用 | |
CN104945352A (zh) | 一种哌嗪苯二腈类化合物及其应用 | |
CN101119972B (zh) | 一种芳基醚类化合物及其制备与应用 | |
JPH07165725A (ja) | ピラゾール誘導体及び除草剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160121 Address after: 110021 Liaodong Road, Tiexi District, Liaoning, No. 8-1, No. Patentee after: SHENYANG SINOCHEM PESTICIDE CHEMICAL RESEARCH AND DEVELOPMENT CO., LTD. Address before: 28, Fuxing Avenue, Xicheng District, Beijing, China Patentee before: Sinochem Corporation Patentee before: Shenyang Research Institute of Chemical Industry |