CN100408565C - 杀虫的1-芳基-3偕胺肟-吡唑衍生物 - Google Patents
杀虫的1-芳基-3偕胺肟-吡唑衍生物 Download PDFInfo
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- CN100408565C CN100408565C CNB2003801048582A CN200380104858A CN100408565C CN 100408565 C CN100408565 C CN 100408565C CN B2003801048582 A CNB2003801048582 A CN B2003801048582A CN 200380104858 A CN200380104858 A CN 200380104858A CN 100408565 C CN100408565 C CN 100408565C
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- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
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- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OEJNXTAZZBRGDN-UHFFFAOYSA-N toxaphene Chemical compound ClC1C(Cl)C2(Cl)C(CCl)(CCl)C(=C)C1(Cl)C2(Cl)Cl OEJNXTAZZBRGDN-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
Abstract
本发明涉及式(Ia)或(Ib)的1-芳基吡唑-3-取代的-偕胺肟衍生物或其盐:其中各种符号如说明书所定义,并且涉及其杀虫组合物、其制备方法,以及用于控制节肢动物(包括昆虫和蜘蛛类动物)和蠕虫(包括线虫)的用途。
Description
本发明涉及1-芳基吡唑-3-取代的-偕胺肟衍生物、其制备方法及其组合物,并且涉及将其用于控制害虫如有害节肢动物(包括昆虫和蜘蛛类动物)和蠕虫(包括线虫)的用途。
利用1-芳基吡唑化合物控制昆虫、蜘蛛类动物或蠕虫类已经描述于例如专利公开号WO 93/06089、WO 94/21606、WO 87/03781、EP0295117、EP 659745、EP 679650、EP 201852和U.S.5,232,940中。利用1-芳基吡唑化合物控制动物寄生虫也描述于例如专利公开号WO00/35884、EP 0846686、WO 98/24769和WO 97/28126中。
尤其是WO 98/28278和WO 97/28126描述了某些1-芳基吡唑-3-取代的-偕胺肟衍生物以及其它相关化合物,然而其中并没有特别提到经苄基取代和杂环基取代的偕胺肟化合物,也没有暗示所述化合物也可以用作杀虫剂。
然而在所有应用领域中,这些现有化合物的活性水平和/或活性持久性不能完全令人满意,尤其是防治某些生物或当低浓度施用时。
由于现代杀虫剂必须满足广泛的需求,例如有关活性水平、持久性以及作用谱、使用谱、毒性、与其它活性成分的组合、与助剂的组合或合成,以及可能出现的抗药性,因此对这类物质的开发永远不能终止,目前对于优于已知化合物的新化合物(至少对所关注的某些方面来说)有持续的大量需求。
本发明提供一种式(Ia)或(Ib)的1-芳基吡唑-3-取代的-偕胺肟衍生物化合物或其杀虫可接受的盐:
其中:
R1为未经取代或经一个或多个R15基团取代的芳基;或为R10或R19;
X和Y各自独立地为H、(C3-C6)-链烯基、(C3-C6)-卤烯基、(C3-C6)-炔基、(C3-C6)-卤炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CONR7R8、CONR8R9、-CO2-(CH2)qR7、-(CH2)qR7、-(CH2)qR10、COR8、SO2R13或COR17;或为未经取代或经一个或多个R11基团取代的(C1-C6)-烷基;
W为N、C-CH3或C-卤素;
R2为氢、CH3或卤素;
R3为卤素、(C1-C3)-烷基、(C1-C3)-卤烷基、(C1-C3)-卤烷氧基、S(O)p-(C1-C3)-卤烷基或SF5;
R4为H、(C3-C6)-链烯基、(C3-C6)-卤烯基、(C3-C6)-炔基、(C3-C6)-卤炔基、(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、-CO2-(C3-C7)-环烷基、-CO2-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C3-C6)-链烯基、-CO2-(CH2)qR7、CONR8R9、-CO2-(CH2)qR10、-(CH2)qR7、-(CH2)qR10、COR8或COCH2O-(C1-C4)-烷基;或为未经取代或经一个或多个R11基团取代的(C1-C6)-烷基;
R5为H、(C2-C6)-炔基、-CO2-(C1-C6)-烷基、(C3-C7)-环烷基-SO2R12;或为(C1-C6)-烷基、(C2-C6)-链烯基或CO-(C1-C6)-烷基,最后三个所述基团是未经取代或经一个或多个R11基团取代的;
R6和R13各自独立地为(C1-C6)-烷基、(C1-C6)-卤烷基、(C2-C6)-链烯基、(C2-C6)-卤烯基、(C2-C6)-炔基、(C2-C6)-卤炔基或(C3-C7)-环烷基;
R7为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、CN、NO2、S(O)pR13和NR9R14;
R8为H、(C1-C6)-烷基、(C1-C6)-卤烷基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-(CH2)qR7或-(CH2)qR10;
R9和R14各自独立地为H、(C1-C6)-烷基、(C1-C6)-卤烷基、(C3-C7)-环烷基或-(C1-C4)-烷基-(C3-C7)-环烷基;或
R8和R9与相连的N原子一起形成5或6元饱和环,在环上任选地含有选自O、S和N的另外的杂原子,该环是未经取代的或经一个或多个选自下组的基团取代的:卤素、(C1-C6)-烷基和(C1-C6)-卤烷基;
R10为未经取代或经一个或多个选自下组的基团取代的杂环基:卤素、(C1-C4)-烷基、(C1-C4)-卤烷基、(C1-C4)-烷氧基、S(O)pR13、OH和氧代;
R11为卤素、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、(C3-C7)-环烷基、S(O)pR13、-CO2-(C1-C6)-烷基、-O(C=O)-(C1-C6)-烷基、CO-(C1-C6)-烷基、CO-(C1-C6)-卤烷基、NR8R9、CONR8R9、SO2NR8R9、OH、CN、NO2、OR7、NR8COR14、NR8SO2R13或OR10;
R12为(C3-C7)-环烷基、(C2-C6)-链烯基、(C2-C6)-卤烯基或R10;或为未经取代或经一个或多个R15基团取代的苯基;或为未经取代或经一个或多个选自下组的基团取代的(C1-C6)-烷基:卤素、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、(C3-C6)-链烯氧基、(C3-C6)-卤烯氧基、(C3-C6)-炔氧基、(C3-C6)-卤炔氧基、(C3-C7)-环烷基、S(O)pR7、S(O)pR10、S(O)pR13、CN、NO2、OH、COR8、NR8COR14、NR8SO2R13、CONR8R9、NR8R9、OR7、OR10、R16、R10和CO2R8;
R15为卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、CN、NO2、S(O)pR13、NR8R9、COR13、COR7、CONR8R9、SO2NR8R9、R7、SF5、OH、OR7、R18、OR18、SO3H或(C1-C6)-亚烷基亚氨基;
R16为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、CN、NO2、S(O)pR13、NR8R9、COR13、COR7、CONR8R9、SO2NR8R9、OH、SO3H和(C1-C6)-亚烷基亚氨基;
R17为经(C1-C6)-烷氧基、S(O)p-(C1-C6)-烷基或S(O)p-(C1-C6)-卤烷基取代的(C1-C6)-烷基;
R18为选自下组的杂芳基:吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噻吩基、噻唑基、噻二唑基、噁唑基、异噁唑基、呋喃基、吡咯基、吡唑基、咪唑基和三唑基,这些基团是未经取代或经一个或多个选自下组的基团取代的:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基和(C1-C6)-烷氧基;
R19为选自下组的杂芳基:吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噻吩基、噻唑基、噻二唑基、噁唑基、异噁唑基、呋喃基、吡咯基、吡唑基、咪唑基和三唑基,这些基团是未经取代或经一个或多个选自下组的基团取代的:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基和(C1-C6)-烷氧基,并且这些杂芳基是经R7、R18或OR7取代的;
m为1或2;
n和p各自独立地为0、1或2;
q为0或1;并且
在上述基团中的每个杂环基独立地为具有3至6个环原子,以及在环中具有选自N、O和S的1、2或3个杂原子的杂环基团。
这些化合物具有颇有价值的杀虫特性。
本发明还包括上述化合物的任何立体异构体、对映异构体或几何异构体,以及它们的混合物。
其中Y为H的式(Ia)和(Ib)化合物可以以如下所示的互变异构形式存在:
这类互变异构体是熟知的并且描述于S.Patai(The Chemistry ofFunctional Groups:Amidines and Imidates,第二卷,1991,第276-277页)中。应理解为所有的这类互变异构体均包含在本发明中。
术语“杀虫可接受的盐”指其阳离子或阴离子是已知的、并且可用于在本领域形成杀虫用途的盐。
适宜的具有碱基的盐类,例如由含有羧酸基团的式(I)化合物形成的盐,包括碱金属(如钠和钾)、碱土金属(如钙和镁)、铵和胺(如二乙醇胺、三乙醇胺、辛胺、吗啉和二辛基甲胺)的盐类。适宜的酸加成盐,如由含氨基的式(I)化合物形成的盐,包括与无机酸形成的盐,例如盐酸盐、硫酸盐、磷酸盐和硝酸盐以及与有机酸如乙酸形成的盐。
应理解为上述包括的附带条件仅仅是因为排除化学不稳定的基团,而非现有技术的原因。
在本发明的说明书中,包括所附的权利要求书中,上述的取代基具有如下含义:
卤素指氟、氯、溴或碘。
在基团名称前的术语“卤”指该基团部分或完全被卤代,即,以任何组合被F、Cl、Br或I取代,优选被F或Cl取代。
烷基和烷基部分(除非另外定义)为直链或支链。
表达式“(C1-C6)烷基”应理解为指具有1、2、3、4、5或6个碳原子的直链或支链烃基,如甲基、乙基、丙基、异丙基、1-丁基、2-丁基、2-甲基丙基或叔丁基。
烷基和其复合基团,除非另外定义,优选地具有1至4个碳原子。
“(C1-C6)卤烷基”指在所述表达式“(C1-C6)烷基”中,一个或多个氢原子由相同数量的相同或不同卤素原子所替代的烷基,如单卤烷基、全卤烷基,CF3、CHF2、CH2F、CHFCH3、CF3CH2、CF3CF2、CHF2CF2、CH2FCHCl、CH2Cl、CCl3、CHCl2或CH2CH2Cl。
表达式“(C1-C12)-亚烷基”应理解为指具有1至12个碳原子的直链或支链饱和碳链。
表达式“(C1-C12)-卤代亚烷基”应理解为指具有1至12个碳原子的直链或支链饱和碳链,其中一个或多个氢原子由相同数量的相同或不同卤素原子替代。
表达式“(C2-C12)-亚烯基”应理解为具有2至12个碳原子的直链或支链饱和碳链,并且其包含至少一个可位于各自不饱和基团的任何位置的双键。
“(C1-C6)烷氧基”指其碳链具有表达式“(C1-C6)烷基”所述含义的烷氧基。“卤烷氧基”为例如OCF3、OCHF2、OCH2F、CF3CF2O、OCH2CF3或OCH2CH2Cl。
“(C2-C6)-链烯基”指具有相应于该限定范围的碳原子数的直链或支链无环碳链,并且包含至少一个可位于各自不饱和基团的任何位置的双键。“(C2-C6)-链烯基”相应地指例如乙烯基、烯丙基、2-甲基-2-丙烯基、2-丁烯基、戊烯基、2-甲基戊烯基或己烯基。
“(C2-C6)炔基”指具有相应于该限定范围的碳原子数的直链或支链无环碳链,并且包含至少一个可位于各自不饱和基团的任何位置的三键。“(C2-C6)炔基”相应地指例如炔丙基、1-甲基-2-丙炔基、2-丁炔基或3-丁炔基。
环烷基优选在环上具有3至7个碳原子并且任选地被卤素或烷基取代。
在式(I)化合物中,提供下面的基团实例。
经环烷基取代的烷基实例是环丙基甲基;
经烷氧基取代的烷基实例是甲氧基甲基(CH3OCH2-);和
经烷硫基取代的烷基实例是甲基硫代甲基(CH3SCH2-)。
芳基单或二环芳族系,例如苯基、萘基、四氢萘基、茚基、茚满基等,优选苯基。
“杂环基”可以为饱和的、不饱和的或杂芳族的基团;其优选在杂环上包含一个或多个,优选1、2或3个杂原子,杂原子优选选自N、O和S;该基团优选地为具有3至7个环原子的脂肪族杂环基,或具有5或6个环原子的杂芳族基团。该杂环基可以为例如杂芳族基团或环(杂芳基),如其中至少一个环包含一个或多个杂原子的单、二或多环芳族系,例如吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噻吩基、噻唑基、噻二唑基、噁唑基、异噁唑基、呋喃基、吡咯基、吡唑基、咪唑基和三唑基,或者是部分或完全氢化的基团如环氧乙烷、氧杂环丁基、氧杂环戊基(四氢呋喃基)、氧杂环己基、吡咯烷基、哌啶基、哌嗪基、二氧杂环戊基、噁唑啉基、异噁唑啉基、噁唑烷基、异噁唑烷基和吗啉基。“杂环基”可以是未经取代的或经一个或多个(优选1、2或3个基团)选自下组的基团取代的:卤素、烷氧基、卤烷氧基、烷硫基、羟基、氨基、硝基、羧基、氰基、烷氧羰基、烷基羰基、甲酰基、氨基甲酰基、单和二烷基氨基羰基、经取代的氨基如酰氨基、单和二烷基氨基,以及烷基亚磺酰基、卤烷基亚磺酰基、烷基磺酰基、卤烷基磺酰基、烷基和卤烷基,以及还有氧代。氧代基团可以存在于可能有多个氧化数的杂环原子上,例如在N和S情形下。
术语“害虫”指节肢动物害虫(包括昆虫和蜘蛛类动物),和蠕虫(包括线虫)。
式(Ib)化合物是优选的。
优选R1为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、(C1-C6)-卤烷氧基、CN、NO2、S(O)pR13、NR8R9、COR13和CONR8R9;(更优选R1为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C3)-烷基、(C1-C3)-卤烷基、(C1-C3)-烷氧基、(C1-C3)-卤烷氧基、CN、NO2、S(O)pR13和NR8R9);并且其中优选地
R8和R9各自独立地为H或(C1-C6)-烷基,或R8和R9与相连的N原子一起形成5或6元饱和环,在环上任选地含有选自O、S和N的另外的杂原子,该环是未经取代的或经一个或多个(C1-C3)-烷基取代的;
并且R13为(C1-C3)-烷基或(C1-C3)-卤烷基。
优选X和Y各自独立地为H、(C1-C6)-烷基或CO(C1-C6)-烷基。
优选W为C-Cl。
优选R2为Cl。
优选R3为CF3或OCF3(更优选R3为CF3)。
优选R4为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、-(C1-C6)-烷基-(C3-C7)-环烷基、COCH2O(C1-C4)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基或-CH2R7,其中R7为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C3)-烷基、(C1-C3)-卤烷基、(C1-C3)-烷氧基、(C1-C3)-卤烷氧基、CN、NO2和S(O)pR13,并且R13为(C1-C3)-烷基或(C1-C3)-卤烷基。
优选R5为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-CO2-(C1-C6)-烷基或-(C1-C6)-烷基-(C3-C7)-环烷基。
优选R6为CF3。
优选m为1。
优选上述基团中的杂环独立地为具有3至6个环原子,以及在环中具有选自N、O和S的1、2或3个杂原子的杂环基团,该杂环基团是未经取代或经一个或多个选自下组的基团取代的:卤素、(C1-C4)-烷基、(C1-C4)-卤烷基和(C1-C4)-烷氧基(更优选上述基团中的杂环独立地为具有5或6个环原子,以及在环中具有选自N、O和S的1、2或3个杂原子的杂环基团,该杂环基团是未经取代或经一个或多个选自下组的基团取代的:卤素、(C1-C4)-烷基、(C1-C4)-卤烷基和(C1-C4)-烷氧基)。
优选的式(Ib)化合物类是其中:
R1为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、S(O)p-(C1-C6)-烷基或S(O)p-(C1-C6)-卤烷基;或为吡啶基、嘧啶基、噻吩基、噻唑基、呋喃基、四氢呋喃基、吡咯基、吡唑基、咪唑基、三唑基、四氢噻吩基或四唑基,这些基团是未经取代或经一个或多个选自下组的基团取代的:卤素、(C1-C3)-烷基或(C1-C3)-卤烷基;
X为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CO(C1-C6)-烷基、-CH2O-(C1-C6)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基或-CH2苯基;
Y为H;
W为C-Cl;
R2为Cl;
R3和R6各自为CF3;
R4为H、(C1-C6)-烷基、COCH2O(C1-C4)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基或-CH2苯基;
R5为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CO(C1-C6)-烷基、-CH2O-(C1-C6)-烷基、-(C1-C6)-烷基S(O)p-(C1-C6)-烷基、SO2(C1-C6)-烷基、SO2(C1-C6)-卤烷基或SO2CH2苯基;和
m为1或2。
优选的式(Ia)化合物类是其中:
R1为苯基;
Y为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CO(C1-C6)-烷基、-CH2O-(C1-C6)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基、SO2(C1-C6)-烷基、SO2(C1-C6)-卤烷基或SO2CH2苯基;
X为H;
W为C-Cl;
R2为Cl;
R3和R6各自为CF3;
R4为H、(C1-C6)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基或-CH2苯基;
R5为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CO(C1-C6)-烷基、-CH2O-(C1-C6)-烷基、-(C1-C6)-烷基S(O)p-(C1-C6)-烷基、SO2(C1-C6)-烷基、SO2(C1-C6)-卤烷基或SO2CH2苯基;和
m为1。
更优选的式(Ia)化合物类是其中:
R1为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、(C1-C6)-烷氧基、S(O)p-(C1-C6)-烷基和S(O)p-(C1-C6)-卤烷基;
X为H、(C1-C6)-烷基、(C3-C6)-链烯基、(C3-C6)-炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基、-CO2-(C1-C6)-烷基、CO(C1-C6)-烷基、CON[(C1-C6)-烷基]2、-CH2O-(C1-C6)-烷基、-(C1-C6)-烷基-S(O)p-(C1-C6)-烷基或经一个或多个选自下组的基团取代的-CH2苯基:卤素、(C1-C3)-烷基或(C1-C3)-烷氧基;
Y为(C1-C6)-烷基;
W为C-Cl;
R2为Cl;
R3和R6各自为CF3;
R4为(C1-C6)-烷基或-(C2-C4)-烷基-S(O)p-(C1-C4)-烷基;
R5为H或CH3;并且
m为1。
最优选的式(Ia)或(Ib)化合物类是其中:
R1为苯基;
X和Y各自独立地为H、甲基或乙酰基;
W为C-Cl;
R2为Cl;
R3和R6各自为CF3;
R4和R5各自独立地为H、甲基、乙基、烯丙基、炔丙基、环丙基、苄基、环丙基甲基、甲基硫代乙基、乙氧基乙酰基或乙氧基羰基;并且
m为1。
通式(I)化合物可通过已知方法的应用或改进加以制备(即迄今为止在化学文献中所采用的或描述的方法)。应理解在某些情形下为了获得令人满意的产率,利用本领域熟知的保护剂是必须的。
在如下的方法描述中,当没有对式中所出现的符号进行特别定义时,应理解为“如上所定义”,其与说明书中对每个符号首次定义相一致。
根据本发明的一个特征,式(Ia)化合物(其中X为H,m和R1如上所定义,Y为不包括氢的如上所定义的基团,并且其它符号如上所定义)可通过将式(II)化合物与式(III)化合物反应制得:
其中,R2、R3、R4、R5、R6、W和n如上所定义,
Y-NH-O(CH2)mR1
(III)
其中R1和m如上所定义,并且Y为不包括氢的如上所定义的基团。该反应通常于温度为0至100℃(优选0至50℃)下,在碱如三烷基胺如三乙胺存在下,在溶剂如甲醇中进行。
根据本发明的另一特征,式(Ia)化合物(其中X为H,m和R1如上所定义,Y为不包括氢的如上所定义的基团,并且其它符号如上所定义)可通过将式(IV)化合物与式(V)化合物反应制得:
其中各种符合如上所定义,
L-(CH2)mR1 (V)
其中R1和m如上所定义,并且L为离去基团如卤素(优选氯)或磺酰氧基(sulfonyloxy)。该反应通常于温度为0至100℃(优选0至50℃)下,在碱如氢化钠存在下,在溶剂如四氢呋喃或N,N-二甲基甲酰胺中进行。
根据本发明的另一特征,式(Ia)化合物(其中X为不包括氢的如上所定义的基团,并且其它符号如上所定义)可以通过利用式(VI)化合物烷基化、酰化或磺酰化相应的式(Ia)化合物(其中X为H)加以制备:
X-L1 (VI)
其中X为不包括氢的如上所定义的基团,L1为离去基团如卤素(优选为氯)或磺酰氧基。
烷基化反应(当X为(C3-C6)-链烯基、(C3-C6)-卤烯基、(C3-C6)-炔基、(C3-C6)-卤炔基、(C3-C7)-环烷基、-(C1-C4)-烷基-(C3-C7)-环烷基或未经取代或经一个或多个R11基团取代的(C1-C6)-烷基;或X为-(CH2)qR7、-(CH2)qR10并且q为0)通常于温度为0至100℃(优选0至50℃)下,在碱如氢化钠存在下,在溶剂如四氢呋喃或N,N-二甲基甲酰胺中进行。对于其中X为-(CH2)qR7、-(CH2)qR10并且q为1的烷基化反应(即芳基化反应)来说,L1优选为氟。
磺酰化反应(当X为SO2R13)通常于温度为0至100℃(优选0至50℃)下,在碱如氢化钠存在下,在溶剂如四氢呋喃或N,N-二甲基甲酰胺中进行。
酰化反应(当X为-CO2-(C1-C6)-烷基、CONR7R8、CONR8R9、-CO2-(CH2)qR7、COR8或COR17)通常于温度为0至100℃(优选0至50℃)下,在碱如三乙胺存在下,在溶剂如四氢呋喃中进行。
根据本发明的另一特征,式(Ia)化合物(其中X、Y和其它符号如上所定义)可以通过式(VII)化合物与上述式(V)化合物反应加以制备:
其中各种符号如上所定义。该反应通常于温度为0至100℃(优选0至50℃)下,在碱如氢化钠存在下,在溶剂如四氢呋喃或N,N-二甲基甲酰胺中进行。
根据本发明的另一特征,式(Ib)化合物(其中X和Y均为H,并且m、R1和其它符号如上所定义)可以通过如上所定义的式(II)化合物与式(VIII)化合物反应加以制备:
NH2-O(CH2)mR1
(VIII)
其中R1和m如上所定义。该反应通常于温度为0至100℃(优选0至50℃)下,在碱如三烷基胺例如三乙胺存在下,在溶剂如甲醇中进行。
根据本发明的另一特征,式(Ib)化合物(其中X为H,Y为不包括氢的如上所定义的基团,并且其它符号如上所定义)可以通过利用式(IX)化合物烷基化、酰化或磺酰化相应的式(Ib)化合物(其中Y为H)加以制备:
Y-L2 (IX)
其中Y为不包括氢的如上所定义的基团,L2为离去基团如卤素(优选氯)或磺酰氧基。
该烷基化、酰化或磺酰化反应可以根据上述由式(VI)化合物制备式(Ia)化合物的方法加以进行。
根据本发明的另一特征,式(Ib)化合物(其中X和Y为不包括氢的如上所定义的基团,并且其它符号如上所定义,该化合物可以通过利用如上所定义的式(VI)化合物烷基化、酰化或磺酰化相应的式(Ib)化合物(其中X为H)加以制备。
该烷基化、酰化或磺酰化反应可以根据上述由式(VI)化合物制备式(Ia)化合物的方法加以进行。
根据本发明式(I)化合物的另一特征,其中R1、R2、R3、R4、R5、R6、W、X、Y和m如上所定义,并且n为1或2,该化合物可以通过氧化相应化合物(其中n为0或1)加以制备。该氧化反应通常于温度为0至溶剂的回流温度下,在溶剂如二氯甲烷或1,2-二氯乙烷中,利用过酸如3-氟过苯甲酸进行反应。
通过上述方法可以合成式(I)化合物的集合,也可以用并列进行的方式加以制备,并且其可以用手工、半自动或全自动的方式进行。在此有可能例如将反应操作、产物或中间产物的处理或提纯自动化。总体上对此理解为一种例如通过S.H.DeWitt在“Annual Reports inCombinatorial Chemistry and Molecular Diversity:Automatedsynthesis(组合化学和分子多样性年报:自动化合成)”,第1册,Verlag Escom 1997,第69至77页所描述的操作。
一系列的商购可得的装置可以用于并行的反应操作及处理,例如Stem公司(Woodrolfe Road,Tollesbury,Essex,CM98SE,英国),或H+P Labortechnik GmbH,Bruckmannring 28,85764Oberschleiβheim,德国,或Radleys公司(Shirehill,Saffron Walden,Essex,英国)提供的装置。用于并列进行提纯式(I)的化合物或在制备过程中出现的中间产物的装置还有色谱仪,例如公司ISCO,Inc.,4700 Superior Street,Lincoln,NE 68504,USA的装置。
所述装置导致其中将各个工作步骤自动化、在工作步骤之间却必须手工操作进行的具有标准组件的工艺流程。这也可以通过使用部分或完全整合的自动化体系而避免,其中将需要的自动化组件例如通过机器人操作。所述自动化系统例如可从Zymark Corporation,ZymarkCenter,Hopkinton,MA 01748,USA获得。
在此描述之外,式(I)化合物可以部分或完全通过固相辅助的方法制备。对此,将合成或为适于所需操作的经改进的合成的各中间步骤或所有中间步骤与合成树脂相结合。固相辅助的合成方法在专业文献中有足够的描述,例如Barry A.Bunin在“组合标记(TheCombinatorial Index)”,Academic Press,1998中的描述。
对于经固相辅助的合成方法的应用有一系列文献已知的报告,其相序可以手工或自动方式实施。例如所使用的“茶包法”(Houghten,US 4,631,211;Houghten等人,Proc.Natl.Acad.Sci.1985,82,5131-5135)可以半自动化,其是IRORI公司(11149 North TorreyPines Road,La Jolla,CA 92037,USA)的产品。经固相辅助的并行合成法例如可通过公司Argonaut Technologies,Inc.,(887 IndustrialRoad,San Carlos,CA 94070,USA)或MultiSyn Tech GmbH(Wullener Feld 4,58454 Witten,德国)的装置达到自动化。
在此描述的制备方法获得以物质集合的形式(称之为集合库)的式(I)化合物。本发明也涉及包含至少两种式(I)化合物的集合库。
如上所定义的式(IV)中间体可以通过如上所定义的式(II)化合物与式(X)反应加以制备:
Y-NHOH (X)
其中Y如上所定义。该反应可以利用由式(III)和(II)化合物制备式(Ia)化合物的上述操作加以进行。
如上所定义的式(VII)中间体可以通过如上所定义的式(IV)化合物与如上所定义的式(VI)化合物反应制得。该反应可以利用上述通过利用式(VI)化合物烷基化、酰化和磺酰化相应的式(Ia)化合物制备式(Ia)化合物的操作加以进行。
某些式(IV)和(VII)化合物是新的并且以其形成本发明进一步的特征。
式(II)、(III)、(V)、(VI)、(VIII)、(IX)和(X)化合物是已知的或可以通过已知方法制备的。
下面的非限制性实施例说明式(I)化合物的制备。
化学实施例
下面的实施例中,除非另有说明,数量值(以及百分比)是基于重量的。
实施例1:
1-(2,6-二氯-4-三氟甲基苯基)-3-(N-苄氧基-2-脒基)-5-甲基氨基-4-三氟甲基磺酰基吡唑(化合物1-49)
将O-苄基胲氢氯化物(0.214g,1.34mmol)和三乙胺(0.33g,3.3mmol)加至1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-甲基氨基-4-三氟甲基磺酰基吡唑(0.5g,1.1mmol)的甲醇溶液中。将混合物于20℃下搅拌,直到获得清液,随后蒸发。加入水和乙酸乙酯进行萃取处理后,获得白色固体状的标题产物(0.387g)。
实施例2:
1-(2,6-二氯-4-三氟甲基苯基)-3-[N-(2,6-二氯苄氧基)-N-甲基-2-脒基]-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(化合物4-82)
将氢化钠(90%,0.029g,1.1mmol)加至1-(2,6-二氯-4-三氟甲基苯基)-3-(N-羟基-N-甲基-2-脒基)-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(0.5g,1.0mmol)的N,N-二甲基甲酰胺溶液中。于20℃下搅拌0.5小时后,滴加2,6-二氯苄基溴化物(0.252g,1.05mmol)。将混合物于20℃下再搅拌7小时。在加入含水氯化铵后,进行萃取处理,采用色谱分析分离到固体状的标题产物(0.31g)。
实施例3:
1-(2,6-二氯-4-三氟甲基苯基)-3-[N-甲基-N-(4-三氟甲基苄氧基)-2-脒基]-5-甲基氨基-4-三氟甲基磺酰基吡唑(化合物4-128)
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-(N-羟基-N-甲基-2-脒基)-5-甲基氨基-4-三氟甲基磺酰基吡唑(0.5g,1.0mmol)、氢化钠(90%,0.029g,1.1mmol)和4-三氟甲基苄基溴化物外,根据实施例2的方法进行反应,获得固体状的标题化合物(0.57g)。
实施例4:
1-(2,6-二氯-4-三氟甲基苯基)-3-[N-甲基-N-(4-三氟甲氧基苄氧基)-2-脒基]-5-甲基氨基-4-三氟甲基硫代吡唑(化合物4-165)
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-(N-羟基-N-甲基-2-脒基)-5-甲基氨基-4-三氟甲基硫代吡唑(0.5g,1.0mmol)、氢化钠(90%,0.029g,1.1mmol)和4-三氟甲氧基苄基溴化物(0.290g,1.05mmol)外,根据实施例2的方法进行反应,获得固体状的标题化合物(0.093g)。
实施例5:
1-(2,6-二氯-4-三氟甲基苯基)-3-[N-甲基-N-(4-三氟甲基苄氧基)-2-脒基]-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(化合物4-93)
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-(N-羟基-N-甲基-2-脒基)-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(0.5g,1.0mmol)、氢化钠90%(0.029g,1.1mmol)和4-三氟甲基苄基溴化物(0.251g,1.05mmol)外,根据实施例2的方法进行反应,并且随后通过色谱分析进行纯化,获得固体状的1-(2,6-二氯-4-三氟甲基苯基)-3-[N-甲基-N-(4-三氟甲基苄氧基)-2-脒基]-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(0.018g)。
实施例6:
1-(2,6-二氯-4-三氟甲基苯基)-3-[N-(4-氟苄氧基-N-甲基)-N’-(4-氟苄基)-2-脒基]-5-甲基氨基-4-三氟甲基磺酰基吡唑(化合物4-159)
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-(N-甲基-N-羟基-2-脒基)-5-甲基氨基-4-三氟甲基磺酰基吡唑(0.5g,1.0mmol)、氢化钠(90%,0.029g,1.1mmol)和4-氟苄基溴化物(0.202g,1.05mmol)外,根据实施例2的方法进行反应,获得固体状的标题化合物(0.309g)。
下述参考实施例说明制备在上述实施例合成中使用的中间体。
中间体实施例1:
1-(2,6-二氯-4-三氟甲基苯基)-3-(N-羟基-N-甲基-2-脒基)-5-甲基氨基-4-三氟甲基亚磺酰基吡唑
将N-甲胲氢氯化物(3.45g,41.55mmol)和三乙胺(10.05g,13.9ml,99.0mmol)加至1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(2.0g,4.0mmol)的甲醇溶液中。将混合物于20℃下搅拌8小时,蒸发并且用水洗涤所得固体,过滤并且干燥,获得灰白色固体状的标题产物(14.73g)。
中间体实施例2:
1-(2,6-二氯-4-三氟甲基苯基)-3-(N-苄基-N-羟基-2-脒基)-5-甲基氨基-4-三氟甲基亚磺酰基吡唑
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-甲基氨基-4-三氟甲基亚磺酰基吡唑(0.5g,1.1mmol)、N-苄基胲氢氯化物(0.22g,1.34mmol)外,根据中间体实施例1的方法进行反应,获得白色固体状的标题化合物(0.450g)。
中间体实施例3:
3-(N-苄基-N-羟基-2-脒基)-1-(2,6-二氯-4-三氟甲基苯基)-5-甲基氨基-4-三氟甲基硫代吡唑
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-甲基氨基-4-三氟甲基硫代吡唑(0.5g,1.1mmol)和N-苄基胲氢氯化物(0.22g,1.34mmol)外,根据中间体实施例1的方法进行反应,获得白色固体状的标题化合物(0.435g)。
中间体实施例4:
3-(N-苄基-N-羟基-2-脒基)-1-(2,6-二氯-4-三氟甲基苯基)-5-甲基氨基-4-三氟甲基磺酰基吡唑
除利用1-(2,6-二氯-4-三氟甲基苯基)-3-氰基-5-甲基氨基-4-三氟甲基磺酰基吡唑(0.5g,1.1mmol)和N-苄基胲氢氯化物(0.22g,1.34mmol)外,根据中间体实施例1的方法进行反应,获得白色固体状的标题化合物(0.61g)。
下面示于表1至7中的优选化合物也是本发明的一部分,并且根据、或类似于上述实施例1至6或上述常规方法制备或可以制备。
在表中,cPr指环丙基并且Ph指苯基。其中原子后省略下标形式应理解为这是有意的,例如CH3指CH3。
给定的化合物号仅用于引用标记的目的。
表1:式(Ib)化合物,其中R2=Cl,W=C-Cl,R3=R6=CF3,m=1,R1=苯基;X=Y=H
化合物号 | R<sup>5</sup> | R<sup>4</sup> | n | m.p.(℃) |
1-1 | H | CH3 | 0 | |
1-2 | CH3 | CH3 | 0 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | n | m.p.(℃) |
1-3 | CH2CH3 | CH3 | 0 | |
1-4 | CH2CH2CH3 | CH3 | 0 | |
1-5 | CH2CH2CH2CH3 | CH3 | 0 | |
1-6 | CH2CHCH2 | CH3 | 0 | |
1-7 | CH2CCH | CH3 | 0 | |
1-8 | C(O)OCH3 | CH3 | 0 | |
1-9 | C(O)OCH2CH3 | CH3 | 0 | |
1-10 | CH2OCH3 | CH3 | 0 | |
1-11 | CH2OCH2CH3 | CH3 | 0 | |
1-12 | CH2cPr | CH3 | 0 | |
1-13 | cPr | CH3 | 0 | |
1-14 | CH3 | CH2Ph | 0 | |
1-15 | H | H | 0 | |
1-16 | H | CH2CH3 | 0 | |
1-17 | H | iPr | 0 | |
1-18 | CH2CH2SCH3 | H | 0 | |
1-19 | CH2CH2SCH3 | CH3 | 0 | |
1-20 | SO2CH2CH3 | CH3 | 0 | |
1-21 | SO2CH2CH2CH2Cl | CH3 | 0 | |
1-22 | SO2CH2Ph | CH3 | 0 | |
1-23 | COCH3 | CH3 | 0 | |
1-24 | COCH2OCH2CH3 | CH3 | 0 | |
1-25 | H | CH3 | 1 | |
1-26 | CH3 | CH3 | 1 | |
1-27 | CH2CH3 | CH3 | 1 | |
1-28 | CH2CH2CH3 | CH3 | 1 | |
1-29 | CH2CH2CH2CH3 | CH3 | 1 | |
1-30 | CH2CHCH2 | CH3 | 1 | |
1-31 | CH2CCH | CH3 | 1 | |
1-32 | C(O)OCH3 | CH3 | 1 | |
1-33 | C(O)OCH2CH3 | CH3 | 1 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | n | m.p.(℃) |
1-34 | CH2OCH3 | CH3 | 1 | |
1-35 | CH2OCH2CH3 | CH3 | 1 | |
1-36 | CH2cPr | CH3 | 1 | |
1-37 | cPr | CH3 | 1 | |
1-38 | CH3 | CH2Ph | 1 | |
1-39 | H | H | 1 | |
1-40 | H | CH2CH3 | 1 | |
1-41 | H | iPr | 1 | |
1-42 | CH2CH2SCH3 | H | 1 | |
1-43 | CH2CH2SCH3 | CH3 | 1 | |
1-44 | SO2CH2CH3 | CH3 | 1 | |
1-45 | SO2CH2CH2CH2Cl | CH3 | 1 | |
1-46 | SO2CH2Ph | CH3 | 1 | |
1-47 | COCH3 | CH3 | 1 | |
1-48 | COCH2OCH2CH3 | CH3 | 1 | |
1-49 | H | CH3 | 2 | 174 |
1-50 | CH3 | CH3 | 2 | |
1-51 | CH2CH3 | CH3 | 2 | |
1-52 | CH2CH2CH3 | CH3 | 2 | |
1-53 | CH2CH2CH2CH3 | CH3 | 2 | |
1-54 | CH2CHCH2 | CH3 | 2 | |
1-55 | CH2CCH | CH3 | 2 | |
1-56 | C(O)OCH3 | CH3 | 2 | |
1-57 | C(O)OCH2CH3 | CH3 | 2 | |
1-58 | CH2OCH3 | CH3 | 2 | |
1-59 | CH2OCH2CH3 | CH3 | 2 | |
1-60 | CH2cPr | CH3 | 2 | |
1-61 | cPr | CH3 | 2 | |
1-62 | CH3 | CH2Ph | 2 | |
1-63 | H | H | 2 | |
1-64 | H | CH2CH3 | 2 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | n | m.p.(℃) |
1-65 | H | iPr | 2 | |
1-66 | CH2CH2SCH3 | H | 2 | |
1-67 | CH2CH2SCH3 | CH3 | 2 | |
1-68 | SO2CH2CH3 | CH3 | 2 | |
1-69 | SO2CH2CH2CH2Cl | CH3 | 2 | |
1-70 | SO2CH2Ph | CH3 | 2 | |
1-71 | COCH3 | CH3 | 2 | |
1-72 | COCH2OCH2CH3 | CH3 | 2 |
表2:式(Ib-1)化合物
化合物号 | X | Z | n | m.p.(℃) |
2-1 | H | H | 0 | |
2-2 | CH3 | H | 0 | |
2-3 | CH2CH3 | H | 0 | |
2-4 | CH2CH2CH3 | H | 0 | |
2-5 | CH2CH2CH2CH3 | H | 0 | |
2-6 | CH2CHCH2 | H | 0 | |
2-7 | CH2CCH | H | 0 | |
2-8 | C(O)OCH3 | H | 0 | |
2-9 | C(O)CH3 | H | 0 | |
2-10 | CH2OCH3 | H | 0 |
化合物号 | X | Z | n | m.p.(℃) | |
2-11 | CH2OCH2CH3 | H | 0 | ||
2-12 | CH2cPr | H | 0 | ||
2-13 | cPr | H | 0 | ||
2-14 | CH2Ph | H | 0 | ||
2-15 | H | H | 1 | ||
2-16 | CH3 | H | 1 | ||
2-17 | CH2CH3 | H | 1 | ||
2-18 | CH2CH2CH3 | H | 1 | ||
2-19 | CH2CH2CH2CH3 | H | 1 | ||
2-20 | CH2CHCH2 | H | 1 | ||
2-21 | CH2CCH | H | 1 | ||
2-22 | C(O)OCH3 | H | 1 | ||
2-23 | C(O)OCH2CH3 | H | 1 | ||
2-24 | CH2OCH3 | H | 1 | ||
2-25 | CH2OCH2CH3 | H | 1 | ||
2-26 | CH2cPr | H | 1 | ||
2-27 | cPr | H | 1 | ||
2-28 | CH2Ph | H | 1 | ||
2-29 | H | H | 2 | ||
2-30 | CH3 | H | 2 | ||
2-31 | CH2CH3 | H | 2 | ||
2-32 | CH2CH2CH3 | H | 2 | ||
2-33 | CH2CH2CH2CH3 | H | 2 | ||
2-34 | CH2CHCH2 | H | 2 | ||
2-35 | CH2CCH | H | 2 | ||
2-36 | C(O)OCH3 | H | 2 | ||
2-37 | C(O)CH3 | H | 2 | ||
2-38 | CH2OCH3 | H | 2 | ||
2-39 | CH2OCH2CH3 | H | 2 | ||
2-40 | CH2cPr | H | 2 |
化合物号 | X | Z | n | m.p.(℃) |
2-41 | cPr | H | 2 | |
2-42 | CH2Ph | H | 2 | |
2-43 | H | 2-Cl | 0 | |
2-44 | H | 3-Cl | 0 | |
2-45 | H | 4-Cl | 0 | |
2-46 | H | 2,5-Cl2 | 0 | |
2-47 | H | 2,6-Cl2 | 0 | |
2-48 | H | 3,4-Cl2 | 0 | |
2-49 | H | 2-F | 0 | |
2-50 | H | 3-F | 0 | |
2-51 | H | 4-F | 0 | |
2-52 | H | 3,4-F2 | 0 | |
2-53 | H | 2,6-F2 | 0 | |
2-54 | H | 4-Br | 0 | |
2-55 | H | 4-I | 0 | |
2-56 | H | 2-CF3 | 0 | |
2-57 | H | 3-CF3 | 0 | |
2-58 | H | 4-CF3 | 0 | |
2-59 | H | 3,5-(CF3)2 | 0 | |
2-60 | H | 4-CF3,2-Cl | 0 | |
2-61 | H | 3-CF3,4-Cl | 0 | |
2-62 | H | 2-OCH3 | 0 | |
2-63 | H | 3-OCH3 | 0 | |
2-64 | H | 4-OCH3 | 0 | |
2-65 | H | 4-SCH3 | 0 | |
2-66 | H | 4-SCF3 | 0 | |
2-67 | H | 4-SF5 | 0 | |
2-68 | H | 3,4-(OCH3)2 | 0 | |
2-69 | H | 4-Ph | 0 | |
2-70 | H | 4-I | 0 | |
2-71 | H | 2-CH3 | 0 |
化合物号 | X | Z | n | m.p.(℃) |
2-72 | H | 3-CH3 | 0 | |
2-73 | H | 2,3-(CH3)2 | 0 | |
2-74 | H | 4-CH3 | 0 | |
2-75 | H | 2,5-(CH3)2 | 0 | |
2-76 | H | 2,6-(CH3)2 | 0 | |
2-77 | H | 3,4-(CH3)2 | 0 | |
2-78 | H | 2-Cl | 1 | |
2-79 | H | 3-Cl | 1 | |
2-80 | H | 4-Cl | 1 | |
2-81 | H | 2,5-Cl2 | 1 | |
2-82 | H | 2,6-Cl2 | 1 | |
2-83 | H | 3,4-Cl2 | 1 | |
2-84 | H | 2-F | 1 | |
2-85 | H | 3-F | 1 | |
2-86 | H | 4-F | 1 | |
2-87 | H | 3,4-F2 | 1 | |
2-88 | H | 2,6-F2 | 1 | |
2-89 | H | 4-Br | 1 | |
2-90 | H | 4-I | 1 | |
2-91 | H | 2-CF3 | 1 | |
2-92 | H | 3-CF3 | 1 | |
2-93 | H | 4-CF3 | 1 | |
2-94 | H | 3,5-(CF3)2 | 1 | |
2-95 | H | 4-CF3,2-Cl | 1 | |
2-96 | H | 3-CF3,4-Cl | 1 | |
2-97 | H | 2-OCH3 | 1 | |
2-98 | H | 3-OCH3 | 1 | |
2-99 | H | 4-OCH3 | 1 | |
2-100 | H | 4-SCH3 | 1 | |
2-101 | H | 4-SCF3 | 1 | |
2-102 | H | 4-SF5 | 1 |
化合物号 | X | Z | n | m.p.(℃) |
2-103 | H | 3,4-(OCH3)2 | 1 | |
2-104 | H | 4-Ph | 1 | |
2-105 | H | 4-I | 1 | |
2-106 | H | 2-CH3 | 1 | |
2-107 | H | 3-CH3 | 1 | |
2-108 | H | 2,3-(CH3)2 | 1 | |
2-109 | H | 4-CH3 | 1 | |
2-110 | H | 2,5-(CH3)2 | 1 | |
2-111 | H | 2,6-(CH3)2 | 1 | |
2-112 | H | 3,4-(CH3)2 | 1 | |
2-113 | H | 2-Cl | 2 | |
2-114 | H | 3-Cl | 2 | |
2-115 | H | 4-Cl | 2 | |
2-116 | H | 2,5-Cl2 | 2 | |
2-117 | H | 2,6-Cl2 | 2 | |
2-118 | H | 3,4-Cl2 | 2 | |
2-119 | H | 2-F | 2 | |
2-120 | H | 3-F | 2 | |
2-121 | H | 4-F | 2 | |
2-122 | H | 3,4-F2 | 2 | |
2-123 | H | 2,6-F2 | 2 | |
2-124 | H | 4-Br | 2 | |
2-125 | H | 4-I | 2 | |
2-126 | H | 2-CF3 | 2 | |
2-127 | H | 3-CF3 | 2 | |
2-128 | H | 4-CF3 | 2 | |
2-129 | H | 3,5-(CF3)2 | 2 | |
2-130 | H | 4-CF3,2-Cl | 2 | |
2-131 | H | 3-CF3,4-Cl | 2 | |
2-132 | H | 2-OCH3 | 2 | |
2-133 | H | 3-OCH3 | 2 |
化合物号 | X | Z | n | m.p.(℃) |
2-134 | H | 4-OCH3 | 2 | |
2-135 | H | 4-SCH3 | 2 | |
2-136 | H | 4-SCF3 | 2 | |
2-137 | H | 4-SF5 | 2 | |
2-138 | H | 3,4-(OCH3)2 | 2 | |
2-139 | H | 4-Ph | 2 | |
2-140 | H | 4-I | 2 | |
2-141 | H | 2-CH3 | 2 | |
2-142 | H | 3-CH3 | 2 | |
2-143 | H | 2,3-(CH3)2 | 2 | |
2-144 | H | 4-CH3 | 2 | |
2-145 | H | 2,5-(CH3)2 | 2 | |
2-146 | H | 2,6-(CH3)2 | 2 | |
2-147 | H | 3,4-(CH3)2 | 2 | |
2-148 | H | 4-C5H11 | 0 | |
2-149 | H | 3,5-Cl2 | 0 | |
2-150 | H | 3,5-Cl2 | 1 | |
2-151 | H | 3,5-Cl2 | 2 |
表3:式(Ia)化合物,其中R2=Cl;W=C-Cl;R3=R6=CF3;m=1;R1=苯基;X=H
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR |
3-1 | H | CH3 | CH3 | 0 | |
3-2 | CH3 | CH3 | CH3 | 0 | |
3-3 | CH2CH3 | CH3 | CH3 | 0 | |
3-4 | CH2CH2CH3 | CH3 | CH3 | 0 | |
3-5 | CH2CH2CH2CH3 | CH3 | CH3 | 0 | |
3-6 | CH2CHCH2 | CH3 | CH3 | 0 | |
3-7 | CH2CCH | CH3 | CH3 | 0 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR | |
3-8 | C(O)OCH3 | CH3 | CH3 | 0 | ||
3-9 | C(O)OCH2CH3 | CH3 | CH3 | 0 | ||
3-10 | CH2OCH3 | CH3 | CH3 | 0 | ||
3-11 | CH2OCH2CH3 | CH3 | CH3 | 0 | ||
3-12 | CH2cPr | CH3 | CH3 | 0 | ||
3-13 | cPr | CH3 | CH3 | 0 | ||
3-14 | CH3 | CH2Ph | CH3 | 0 | ||
3-15 | H | H | CH3 | 0 | ||
3-16 | H | CH2CH3 | CH3 | 0 | ||
3-17 | H | iPr | CH3 | 0 | ||
3-18 | CH2CH2SCH3 | H | CH3 | 0 | ||
3-19 | CH2CH2SCH3 | CH3 | CH3 | 0 | ||
3-20 | SO2CH2CH3 | CH3 | CH3 | 0 | ||
3-21 | SO2CH2CH2CH2Cl | CH3 | CH3 | 0 | ||
3-22 | SO2CH2Ph | CH3 | CH3 | 0 | ||
3-23 | COCH3 | CH3 | CH3 | 0 | ||
3-24 | COCH2OCH2CH3 | CH3 | CH3 | 0 | ||
3-25 | H | CH3 | CH3 | 1 | 2,50d,3H,N-CH3 | |
3-26 | CH3 | CH3 | CH3 | 1 | ||
3-27 | CH2CH3 | CH3 | CH3 | 1 | ||
3-28 | CH2CH2CH3 | CH3 | CH3 | 1 | ||
3-29 | CH2CH2CH2CH3 | CH3 | CH3 | 1 | ||
3-30 | CH2CHCH2 | CH3 | CH3 | 1 | ||
3-31 | CH2CCH | CH3 | CH3 | 1 | ||
3-32 | C(O)OCH3 | CH3 | CH3 | 1 | ||
3-33 | C(O)OCH2CH3 | CH3 | CH3 | 1 | ||
3-34 | CH2OCH3 | CH3 | CH3 | 1 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR | |
3-35 | CH2OCH2CH3 | CH3 | CH3 | 1 | ||
3-36 | CH2cPr | CH3 | CH3 | 1 | ||
3-37 | cPr | CH3 | CH3 | 1 | ||
3-38 | CH3 | CH2Ph | CH3 | 1 | ||
3-39 | H | H | CH3 | 1 | ||
3-40 | H | CH2CH3 | CH3 | 1 | ||
3-41 | H | iPr | CH3 | 1 | ||
3-42 | CH2CH2SCH3 | H | CH3 | 1 | ||
3-43 | CH2CH2SCH3 | CH3 | CH3 | 1 | ||
3-44 | SO2CH2CH3 | CH3 | CH3 | 1 | ||
3-45 | SO2CH2CH2CH2Cl | CH3 | CH3 | 1 | ||
3-46 | SO2CH2Ph | CH3 | CH3 | 1 | ||
3-47 | COCH3 | CH3 | CH3 | 1 | ||
3-48 | COCH2OCH2CH3 | CH3 | CH3 | 1 | ||
3-49 | H | CH3 | CH3 | 2 | ||
3-50 | CH3 | CH3 | CH3 | 2 | ||
3-51 | CH2CH3 | CH3 | CH3 | 2 | ||
3-52 | CH2CH2CH3 | CH3 | CH3 | 2 | ||
3-53 | CH2CH2CH2CH3 | CH3 | CH3 | 2 | ||
3-54 | CH2CHCH2 | CH3 | CH3 | 2 | ||
3-55 | CH2CCH | CH3 | CH3 | 2 | ||
3-56 | C(O)OCH3 | CH3 | CH3 | 2 | ||
3-57 | C(O)OCH2CH3 | CH3 | CH3 | 2 | ||
3-58 | CH2OCH3 | CH3 | CH3 | 2 | ||
3-59 | CH2OCH2CH3 | CH3 | CH3 | 2 | ||
3-60 | CH2cPr | CH3 | CH3 | 2 | ||
3-61 | cPr | CH3 | CH3 | 2 | ||
3-62 | CH3 | CH2Ph | CH3 | 2 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR |
3-63 | H | H | CH3 | 2 | |
3-64 | H | CH2CH3 | CH3 | 2 | |
3-65 | H | iPr | CH3 | 2 | |
3-66 | CH2CH2SCH3 | H | CH3 | 2 | |
3-67 | CH2CH2SCH3 | CH3 | CH3 | 2 | |
3-68 | SO2CH2CH3 | CH3 | CH3 | 2 | |
3-69 | SO2CH2CH2CH2Cl | CH3 | CH3 | 2 | |
3-70 | SO2CH2Ph | CH3 | CH3 | 2 | |
3-71 | COCH3 | CH3 | CH3 | 2 | |
3-72 | COCH2OCH2CH3 | CH3 | CH3 | 2 | |
3-73 | H | CH3 | CH2CH3 | 0 | |
3-74 | H | CH3 | CH2CH2CH3 | 0 | |
3-75 | H | CH3 | CH2CH2CH2CH3 | 0 | |
3-76 | H | CH3 | CH2CHCH2 | 0 | |
3-77 | H | CH3 | CH2CCH | 0 | |
3-78 | H | CH3 | C(O)OCH3 | 0 | |
3-79 | H | CH3 | C(O)OCH2CH3 | 0 | |
3-80 | H | CH3 | CH2OCH3 | 0 | |
3-81 | H | CH3 | CH2OCH2CH3 | 0 | |
3-82 | H | CH3 | CH2cPr | 0 | |
3-83 | H | CH3 | cPr | 0 | |
3-84 | H | CH3 | CH2Ph | 0 | |
3-85 | H | CH3 | H | 0 | |
3-86 | H | CH3 | CH2CH2SCH3 | 0 | |
3-87 | H | CH3 | CH2CH2SCH3 | 0 | |
3-88 | H | CH3 | SO2CH2CH3 | 0 | |
3-89 | H | CH3 | SO2CH2CH2CH2Cl | 0 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR | ||
3-90 | H | CH3 | SO2CH2Ph | 0 | |||
3-91 | H | CH3 | COCH3 | 0 | |||
3-92 | H | CH3 | COCH2OCH2CH3 | 0 | |||
3-93 | H | CH2CH2SCH3 | CH2CH3 | 1 | |||
3-94 | H | CH2CH2SCH3 | CH2CH2CH3 | 1 | |||
3-95 | H | CH2CH2SCH3 | CH2CH2CH2CH3 | 1 | |||
3-96 | H | CH2CH2SCH3 | CH2CHCH2 | 1 | |||
3-97 | H | CH2CH2SCH3 | CH2CCH | 1 | |||
3-98 | H | CH2CH2SCH3 | C(O)OCH3 | 1 | |||
3-99 | H | CH2CH2SCH3 | C(O)OCH2CH3 | 1 | |||
3-100 | H | CH2CH2SCH3 | CH2OCH3 | 1 | |||
3-101 | H | CH2CH2SCH3 | CH2OCH2CH3 | 1 | |||
3-102 | H | CH2CH2SCH3 | CH2cPr | 1 | |||
3-103 | H | CH2CH2SCH3 | cPr | 1 | |||
3-104 | H | CH2CH2SCH3 | CH2Ph | 1 | |||
3-105 | H | CH2CH2SCH3 | H | 1 | |||
3-106 | H | CH2CH2SCH3 | CH2CH2SCH3 | 1 | |||
3-107 | H | CH2CH2SCH3 | CH2CH2SCH3 | 1 | |||
3-108 | H | CH2CH2SCH3 | SO2CH2CH3 | 1 | |||
3-109 | H | CH2CH2SCH3 | SO2CH2CH2CH2Cl | 1 | |||
3-110 | H | CH2CH2SCH3 | SO2CH2Ph | 1 | |||
3-111 | H | CH2CH2SCH3 | COCH3 | 1 | |||
3-112 | H | CH2CH2SCH3 | COCH2OCH2CH3 | 1 | |||
3-113 | H | CH2CH2SO2CH33 | CH2CH3 | 2 | |||
3-114 | H | CH2CH2SO2CH3 | CH2CH2CH3 | 2 | |||
3-115 | H | CH2CH2SO2CH | CH2CH2CH2CH | 2 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR | |
3 | 3 | |||||
3-116 | H | CH2CH2SO2CH3 | CH2CHCH2 | 2 | ||
3-117 | H | CH2CH2SO2CH3 | CH2CCH | 2 | ||
3-118 | H | CH2CH2SO2CH3 | C(O)OCH3 | 2 | ||
3-119 | H | CH2CH2SO2CH3 | C(O)OCH2CH3 | 2 | ||
3-120 | H | CH2CH2SO2CH3 | CH2OCH3 | 2 | ||
3-121 | H | CH2CH2SO2CH3 | CH2OCH2CH3 | 2 | ||
3-122 | H | CH2CH2SO2CH3 | CH2cPr | 2 | ||
3-123 | H | CH2CH2SO2CH3 | cPr | 2 | ||
3-124 | H | CH2CH2SO2CH3 | CH2Ph | 2 | ||
3-125 | H | CH2CH2SO2CH3 | H | 2 | ||
3-126 | H | CH2CH2SO2CH3 | CH2CH2SCH3 | 2 | ||
3-127 | H | CH2CH2SO2CH3 | CH2CH2SCH3 | 2 | ||
3-128 | H | CH2CH2SO2CH3 | SO2CH2CH3 | 2 | ||
3-129 | H | CH2CH2SO2CH3 | SO2CH2CH2CH2Cl | 2 | ||
3-130 | H | CH2CH2SO2CH3 | SO2CH2Ph | 2 | ||
3-131 | H | CH2CH2SO2CH3 | COCH3 | 2 | ||
3-132 | H | CH2CH2SO2CH | COCH2OCH2CH | 2 |
化合物号 | R<sup>5</sup> | R<sup>4</sup> | Y | n | m.p.(℃)/1H-NMR |
3 | 3 |
表4:式(Ia-1)化合物
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
4-1 | CON(CH3)2 | H | 0 | |
4-2 | CH3 | H | 0 | |
4-3 | CH2CH3 | H | 0 | |
4-4 | CH2CH2CH3 | H | 0 | |
4-5 | CH2CH2CH2CH3 | H | 0 | |
4-6 | CH2CHCH2 | H | 0 | |
4-7 | CH2CCH | H | 0 | |
4-8 | C(O)OCH3 | H | 0 | |
4-9 | C(O)CH3 | H | 0 | |
4-10 | CH2OCH3 | H | 0 | |
4-11 | CH2OCH2CH3 | H | 0 | |
4-12 | CH2cPr | H | 0 | |
4-13 | cPr | H | 0 | |
4-14 | CH2Ph | H | 0 | |
4-15 | H | H | 1 |
化合物号 | X | Z | q n | m.p.(℃)/1H-NMR |
4-16 | CH3 | H | 1 | |
4-17 | CH2CH3 | H | 1 | |
4-18 | CH2CH2CH3 | H | 1 | |
4-19 | CH2CH2CH2CH3 | H | 1 | |
4-20 | CH2CHCH2 | H | 1 | |
4-21 | CH2CCH | H | 1 | |
4-22 | C(O)OCH3 | H | 1 | |
4-23 | C(O)OCH2CH3 | H | 1 | |
4-24 | CH2OCH3 | H | 1 | |
4-25 | CH2OCH2CH3 | H | 1 | |
4-26 | CH2cPr | H | 1 | |
4-27 | cPr | H | 1 | |
4-28 | CH2Ph | H | 1 | |
4-29 | H | H | 2 | |
4-30 | CH3 | H | 2 | |
4-31 | CH2CH3 | H | 2 | |
4-32 | CH2CH2CH3 | H | 2 | |
4-33 | CH2CH2CH2CH3 | H | 2 | |
4-34 | CH2CHCH2 | H | 2 | |
4-35 | CH2CCH | H | 2 | |
4-36 | C(O)OCH3 | H | 2 | |
4-37 | C(O)CH3 | H | 2 | |
4-38 | CH2OCH3 | H | 2 | |
4-39 | CH2OCH2CH3 | H | 2 | |
4-40 | CH2cPr | H | 2 | |
4-41 | cPr | H | 2 | |
4-42 | CH2Ph | H | 2 | |
4-43 | H | 2-Cl | 0 | |
4-44 | H | 3-Cl | 0 | |
4-45 | H | 4-Cl | 0 | |
4-46 | H | 2,5-Cl2 | 0 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
4-47 | H | 2,6-Cl2 | 0 | |
4-48 | H | 3,4-Cl2 | 0 | |
4-49 | H | 2-F | 0 | |
4-50 | H | 3-F | 0 | |
4-51 | H | 4-F | 0 | |
4-52 | H | 3,4-F2 | 0 | |
4-53 | H | 2,6-F2 | 0 | |
4-54 | H | 4-Br | 0 | |
4-55 | H | 4-I | 0 | |
4-56 | H | 2-CF3 | 0 | |
4-57 | H | 3-CF3 | 0 | |
4-58 | H | 4-CF3 | 0 | |
4-59 | H | 3,5-(CF3)2 | 0 | |
4-60 | H | 4-CF3,2-Cl | 0 | |
4-61 | H | 3-CF3,4-Cl | 0 | |
4-62 | H | 2-OCH3 | 0 | |
4-63 | H | 3-OCH3 | 0 | |
4-64 | H | 4-OCH3 | 0 | |
4-65 | H | 4-SCH3 | 0 | |
4-66 | H | 4-SCF3 | 0 | |
4-67 | H | 4-SF5 | 0 | |
4-68 | H | 3,4-(OCH3)2 | 0 | |
4-69 | H | 4-Ph | 0 | |
4-70 | H | 4-I | 0 | |
4-71 | H | 2-CH3 | 0 | |
4-72 | H | 3-CH3 | 0 | |
4-73 | H | 2,3-(CH3)2 | 0 | |
4-74 | H | 4-CH3 | 0 | |
4-75 | H | 2,5-(CH3)2 | 0 | |
4-76 | H | 2,6-(CH3)2 | 0 | |
4-77 | H | 3,4-(CH3)2 | 0 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
4-78 | H | 2-Cl | 1 | |
4-79 | H | 3-Cl | 1 | |
4-80 | H | 4-Cl | 1 | |
4-81 | H | 2,5-Cl2 | 1 | |
4-82 | H | 2,6-Cl2 | 1 | 79 |
4-83 | H | 3,4-Cl2 | 1 | |
4-84 | H | 2-F | 1 | |
4-85 | H | 3-F | 1 | |
4-86 | H | 4-F | 1 | |
4-87 | H | 3,4-F2 | 1 | |
4-88 | H | 2,6-F2 | 1 | |
4-89 | H | 4-Br | 1 | |
4-90 | H | 4-I | 1 | |
4-91 | H | 2-CF3 | 1 | |
4-92 | H | 3-CF3 | 1 | |
4-93 | H | 4-CF3 | 1 | 2,50,d,3H,N-CH3 |
4-94 | H | 3,5-(CF3)2 | 1 | |
4-95 | H | 4-CF3,2-Cl | 1 | |
4-96 | H | 3-CF3,4-Cl | 1 | |
4-97 | H | 2-OCH3 | 1 | |
4-98 | H | 3-OCH3 | 1 | |
4-99 | H | 4-OCH3 | 1 | |
4-100 | H | 4-SCH3 | 1 | |
4-101 | H | 4-SCF3 | 1 | 2,51,d,3H,N-CH3 |
4-102 | H | 4-SF5 | 1 | |
4-103 | H | 3,4-(OCH3)2 | 1 | |
4-104 | H | 4-Ph | 1 | |
4-105 | H | 4-I | 1 | |
4-106 | H | 2-CH3 | 1 | |
4-107 | H | 3-CH3 | 1 | |
4-108 | H | 2,3-(CH3)2 | 1 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
4-109 | H | 4-CH3 | 1 | |
4-110 | H | 2,5-(CH3)2 | 1 | |
4-111 | H | 2,6-(CH3)2 | 1 | |
4-112 | H | 3,4-(CH3)2 | 1 | |
4-113 | H | 2-Cl | 2 | |
4-114 | H | 3-Cl | 2 | 2,57,d,3H,N-CH3 |
4-115 | H | 4-Cl | 2 | 175 |
4-116 | H | 2,5-Cl2 | 2 | |
4-117 | H | 2,6-Cl2 | 2 | 80 |
4-118 | H | 3,4-Cl2 | 2 | |
4-119 | H | 2-F | 2 | |
4-120 | H | 3-F | 2 | |
4-121 | H | 4-F | 2 | 2,60,d,3H,N-CH3 |
4-122 | H | 3,4-F2 | 2 | |
4-123 | H | 2,6-F2 | 2 | |
4-124 | H | 4-Br | 2 | |
4-125 | H | 4-I | 2 | |
4-126 | H | 2-CF3 | 2 | |
4-127 | H | 3-CF3 | 2 | |
4-128 | H | 4-CF3 | 2 | 93 |
4-129 | H | 3,5-(CF3)2 | 2 | |
4-130 | H | 4-CF3,2-Cl | 2 | |
4-131 | H | 3-CF3,4-Cl | 2 | |
4-132 | H | 2-OCH3 | 2 | |
4-133 | H | 3-OCH3 | 2 | |
4-134 | H | 4-OCH3 | 2 | |
4-135 | H | 4-SCH3 | 2 | |
4-136 | H | 4-SCF3 | 2 | 62 |
4-137 | H | 4-SF5 | 2 | |
4-138 | H | 3,4-(OCH3)2 | 2 | |
4-139 | H | 4-Ph | 2 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
4-140 | H | 4-I | 2 | |
4-141 | H | 2-CH3 | 2 | |
4-142 | H | 3-CH3 | 2 | |
4-143 | H | 2,3-(CH3)2 | 2 | |
4-144 | H | 4-CH3 | 2 | 81 |
4-145 | H | 2,5-(CH3)2 | 2 | |
4-146 | H | 2,6-(CH3)2 | 2 | |
4-147 | H | 3,4-(CH3)2 | 2 | |
4-148 | H | 4-C5H11 | 0 | |
4-149 | H | 3,5-Cl2 | 0 | |
4-150 | H | 3,5-Cl2 | 1 | |
4-151 | H | 3,5-Cl2 | 2 | |
4-152 | H | 3,5-(CH3)2 | 2 | 64 |
4-153 | H | 2-CN | 2 | 54 |
4-154 | H | 4-叔-C4H9 | 1 | 2,50,d,3H,N-CH3 |
4-155 | H | 4-叔-C4H9 | 2 | 2,60,d,3H,N-CH3 |
4-156 | 3-F-苄基 | 3-F | 2 | 2,60,d,3H,N-CH3 |
4-157 | 2-F-苄基 | 2-F | 2 | 2,61,d,3H,N-CH3 |
4-158 | 2-Cl-苄基 | 2-Cl | 2 | 2,57,d,3H,N-CH3 |
4-159 | 4-F-苄基 | 4-F | 2 | 2,60,d,3H,N-CH3 |
4-160 | 3-Cl-苄基 | 3-Cl | 2 | 2,68,d,3H,N-CH3 |
4-161 | 3-CH3-苄基 | 3-CH3 | 2 | 2,60,d,3H,N-CH3 |
4-162 | 3-OCH3-苄基 | 3-OCH3 | 2 | 2,62,d,3H,N-CH3 |
4-163 | 2-CH3-苄基 | 2-CH3 | 2 | 2,60,d,3H,N-CH3 |
4-164 | 4-叔-C4H9-苄基 | 4-叔-C4H9 | 2 | 2,60,d,3H,N-CH3 |
4-165 | H | 4-OCF3 | 0 |
表5:式(Ib-2)化合物
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
5-1 | H | H | 0 | 油状 |
5-2 | CH3 | H | 0 | |
5-3 | CH2CH3 | H | 0 | |
5-4 | CH2CH2CH3 | H | 0 | |
5-5 | CH2CH2CH2CH3 | H | 0 | |
5-6 | CH2CHCH2 | H | 0 | |
5-7 | CH2CCH | H | 0 | |
5-8 | C(O)OCH3 | H | 0 | |
5-9 | C(O)CH3 | H | 0 | |
5-10 | CH2OCH3 | H | 0 | |
5-11 | CH2OCH2CH3 | H | 0 | |
5-12 | CH2cPr | H | 0 | |
5-13 | cPr | H | 0 | |
5-14 | CH2Ph | H | 0 | |
5-15 | H | H | 1 | |
5-16 | CH3 | H | 1 | |
5-17 | CH2CH3 | H | 1 | |
5-18 | CH2CH2CH3 | H | 1 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
5-19 | CH2CH2CH2CH3 | H | 1 | |
5-20 | CH2CHCH2 | H | 1 | |
5-21 | CH2CCH | H | 1 | |
5-22 | C(O)OCH3 | H | 1 | |
5-23 | C(O)OCH2CH3 | H | 1 | |
5-24 | CH2OCH3 | H | 1 | |
5-25 | CH2OCH2CH3 | H | 1 | |
5-26 | CH2cPr | H | 1 | |
5-27 | cPr | H | 1 | |
5-28 | CH2Ph | H | 1 | |
5-29 | H | H | 2 | |
5-30 | CH3 | H | 2 | |
5-31 | CH2CH3 | H | 2 | |
5-32 | CH2CH2CH3 | H | 2 | |
5-33 | CH2CH2CH2CH3 | H | 2 | |
5-34 | CH2CHCH2 | H | 2 | |
5-35 | CH2CCH | H | 2 | |
5-36 | C(O)OCH3 | H | 2 | |
5-37 | C(O)CH3 | H | 2 | |
5-38 | CH2OCH3 | H | 2 | |
5-39 | CH2OCH2CH3 | H | 2 | |
5-40 | CH2cPr | H | 2 | |
5-41 | cPr | H | 2 | |
5-42 | CH2Ph | H | 2 | |
5-43 | H | 2-Cl | 0 | |
5-44 | H | 3-Cl | 0 | |
5-45 | H | 4-Cl | 0 | |
5-46 | H | 2,5-Cl2 | 0 | |
5-47 | H | 2,6-Cl2 | 0 | |
5-48 | H | 3,4-Cl2 | 0 | |
5-49 | H | 2-F | 0 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
5-50 | H | 3-F | 0 | |
5-51 | H | 4-F | 0 | |
5-52 | H | 3,4-F2 | 0 | |
5-53 | H | 2,6-F2 | 0 | |
5-54 | H | 4-Br | 0 | |
5-55 | H | 4-I | 0 | |
5-56 | H | 2-CF3 | 0 | |
5-57 | H | 3-CF3 | 0 | |
5-58 | H | 4-CF3 | 0 | |
5-59 | H | 3,5-(CF3)2 | 0 | |
5-60 | H | 4-CF3,2-Cl | 0 | |
5-61 | H | 3-CF3,4-Cl | 0 | |
5-62 | H | 2-OCH3 | 0 | |
5-63 | H | 3-OCH3 | 0 | |
5-64 | H | 4-OCH3 | 0 | |
5-65 | H | 4-SCH3 | 0 | |
5-66 | H | 4-SCF3 | 0 | |
5-67 | H | 4-SF5 | 0 | |
5-68 | H | 3,4-(OCH3)2 | 0 | |
5-69 | H | 4-Ph | 0 | |
5-70 | H | 4-I | 0 | |
5-71 | H | 2-CH3 | 0 | |
5-72 | H | 3-CH3 | 0 | |
5-73 | H | 2,3-(CH3)2 | 0 | |
5-74 | H | 4-CH3 | 0 | |
5-75 | H | 2,5-(CH3)2 | 0 | |
5-76 | H | 2,6-(CH3)2 | 0 | |
5-77 | H | 3,4-(CH3)2 | 0 | |
5-78 | H | 2-Cl | 1 | |
5-79 | H | 3-Cl | 1 | |
5-80 | H | 4-Cl | 1 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR | |
5-81 | H | 2,5-Cl2 | 1 | ||
5-82 | H | 2,6-Cl2 | 1 | ||
5-83 | H | 3,4-Cl2 | 1 | ||
5-84 | H | 2-F | 1 | ||
5-85 | H | 3-F | 1 | ||
5-86 | H | 4-F | 1 | ||
5-87 | H | 3,4-F2 | 1 | ||
5-88 | H | 2,6-F2 | 1 | ||
5-89 | H | 4-Br | 1 | ||
5-90 | H | 4-I | 1 | ||
5-91 | H | 2-CF3 | 1 | ||
5-92 | H | 3-CF3 | 1 | ||
5-93 | H | 4-CF3 | 1 | ||
5-94 | H | 3,5-(CF3)2 | 1 | ||
5-95 | H | 4-CF3,2-Cl | 1 | ||
5-96 | H | 3-CF3,4-Cl | 1 | ||
5-97 | H | 2-OCH3 | 1 | ||
5-98 | H | 3-OCH3 | 1 | ||
5-99 | H | 4-OCH3 | 1 | ||
5-100 | H | 4-SCH3 | 1 | ||
5-101 | H | 4-SCF3 | 1 | ||
5-102 | H | 4-SF5 | 1 | ||
5-103 | H | 3,4-(OCH3)2 | 1 | ||
5-104 | H | 4-Ph | 1 | ||
5-105 | H | 4-I | 1 | ||
5-106 | H | 2-CH3 | 1 | ||
5-107 | H | 3-CH3 | 1 | ||
2-108 | H | 2,3-(CH3)2 | 1 | ||
5-109 | H | 4-CH3 | 1 | ||
5-110 | H | 2,5-(CH3)2 | 1 | ||
5-111 | H | 2,6-(CH3)2 | 1 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
5-112 | H | 3,4-(CH3)2 | 1 | |
5-113 | H | 2-Cl | 2 | |
5-114 | H | 3-Cl | 2 | |
5-115 | H | 4-Cl | 2 | |
5-116 | H | 2,5-Cl2 | 2 | |
5-117 | H | 2,6-Cl2 | 2 | |
5-118 | H | 3,4-Cl2 | 2 | |
5-119 | H | 2-F | 2 | |
5-120 | H | 3-F | 2 | |
5-121 | H | 4-F | 2 | |
5-122 | H | 3,4-F2 | 2 | |
5-123 | H | 2,6-F2 | 2 | |
5-124 | H | 4-Br | 2 | |
5-125 | H | 4-I | 2 | |
5-126 | H | 2-CF3 | 2 | |
5-127 | H | 3-CF3 | 2 | |
5-128 | H | 4-CF3 | 2 | |
5-129 | H | 3,5-(CF3)2 | 2 | |
5-130 | H | 4-CF3,2-Cl | 2 | |
5-131 | H | 3-CF3,4-Cl | 2 | |
5-132 | H | 2-OCH3 | 2 | |
5-133 | H | 3-OCH3 | 2 | |
5-134 | H | 4-OCH3 | 2 | |
5-135 | H | 4-SCH3 | 2 | |
5-136 | H | 4-SCF3 | 2 | |
5-137 | H | 4-SF5 | 2 | |
5-138 | H | 3,4-(OCH3)2 | 2 | |
5-139 | H | 4-Ph | 2 | |
5-140 | H | 4-I | 2 | |
5-141 | H | 2-CH3 | 2 | |
5-142 | H | 3-CH3 | 2 |
化合物号 | X | Z | n | m.p.(℃)/1H-NMR |
5-143 | H | 2,3-(CH3)2 | 2 | |
5-144 | H | 4-CH3 | 2 | |
5-145 | H | 2,5-(CH3)2 | 2 | |
5-146 | H | 2,6-(CH3)2 | 2 | |
5-147 | H | 3,4-(CH3)2 | 2 | |
5-148 | H | 4-C5H11 | 0 | |
5-149 | H | 3,5-Cl2 | 0 | |
5-150 | H | 3,5-Cl2 | 1 | |
5-151 | H | 3,5-Cl2 | 2 |
表6:式(Ib)化合物,其中R2=Cl;W=C-Cl;R3=R6=CF3;m=1;R4=Y=H;R5=CH3
化合物号 | X | R<sup>1</sup> | n | m.p.(℃)/1H-NMR |
6-1 | H | 2-吡啶基 | 0 | |
6-2 | H | 3-吡啶基 | 0 | 2,56,d,3H,N-CH3 |
6-3 | H | 3-吡啶基 | 0 | |
6-4 | H | 4-吡啶基 | 0 | |
6-5 | H | 1-嘧啶基 | 0 | |
6-6 | H | 3-嘧啶基 | 0 | |
6-7 | H | 4-嘧啶基 | 0 | |
6-8 | H | 2-噻吩基 | 0 | |
6-9 | H | 3-噻吩基 | 0 | |
6-10 | H | 2-呋喃基 | 0 | |
6-11 | H | 3-呋喃基 | 0 | |
6-12 | H | 2-四氢呋喃基 | 0 | |
6-13 | H | 3-四氢呋喃基 | 0 | |
6-14 | H | 3-吡唑基 | 0 | |
6-15 | H | 4-吡唑基 | 0 | |
6-16 | H | 5-吡唑基 | 0 | |
6-17 | H | 2-咪唑基 | 0 | |
6-18 | H | 4-咪唑基 | 0 | |
6-19 | H | 5-咪唑基 | 0 | |
6-20 | H | 2-噻唑基 | 0 | |
6-21 | H | 4-噻唑基 | 0 | |
6-22 | H | 5-噻唑基 | 0 | |
6-23 | H | 2-四氢噻吩基 | 0 | |
6-24 | H | 2-吡咯基 | 0 | |
6-25 | H | 3-吡咯基 | 0 | |
6-26 | H | 4-吡咯基 | 0 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃)/1H-NMR |
6-27 | H | 1-四唑基 | 0 | |
6-28 | H | 5-四唑基 | 0 | |
6-29 | H | 3-(1,2,4)-三唑基 | 0 | |
6-30 | H | 5-(1,2,4)-三唑基 | 0 | |
6-31 | CH3 | 2-噻吩基 | 0 | |
6-32 | CH2CH3 | 2-噻吩基 | 0 | |
6-33 | CH2CH2CH3 | 2-噻吩基 | 0 | |
6-34 | CH2CH2CH2CH3 | 2-噻吩基 | 0 | |
6-35 | CH2CHCH2 | 1-甲基-4-咪唑基 | 0 | |
6-36 | CH2CCH | 1-甲基-4-咪唑基 | 0 | |
6-37 | C(O)OCH3 | 1,3-二甲基-5-Cl-吡唑基 | 0 | |
6-38 | C(O)CH3 | 2,4-二甲基-5-噻唑基 | 0 | |
6-39 | CH2OCH3 | 5-(2-吡啶基)-2-噻吩基 | 0 | |
6-40 | CH2OCH2CH3 | 2-甲基-5-CF3-4-呋喃基 | 0 | |
6-41 | CH2cPr | 2,5-二甲基-3-噻吩基 | 0 | |
6-42 | H | 2-Cl-5-吡啶基 | 0 | 2,59,d,3H,N-CH3 |
6-43 | H | 2-吡啶基 | 1 | |
6-44 | H | 3-吡啶基 | 1 | |
6-45 | H | 3-吡啶基 | 1 | |
6-46 | H | 4-吡啶基 | 1 | |
6-47 | H | 1-嘧啶基 | 1 | |
6-48 | H | 3-嘧啶基 | 1 | |
6-49 | H | 4-嘧啶基 | 1 | |
6-50 | H | 2-噻吩基 | 1 | |
6-51 | H | 3-噻吩基 | 1 | |
6-52 | H | 2-呋喃基 | 1 | |
6-53 | H | 3-呋喃基 | 1 | |
6-54 | H | 2-四氢呋喃基 | 1 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃)/1H-NMR |
6-55 | H | 3-四氢呋喃基 | 1 | |
6-56 | H | 3-吡唑基 | 1 | |
6-57 | H | 4-吡唑基 | 1 | |
6-58 | H | 5-吡唑基 | 1 | |
6-59 | H | 2-咪唑基 | 1 | |
6-60 | H | 4-咪唑基 | 1 | |
6-61 | H | 5-咪唑基 | 1 | |
6-62 | H | 2-噻唑基 | 1 | |
6-63 | H | 4-噻唑基 | 1 | |
6-64 | H | 5-噻唑基 | 1 | |
6-65 | H | 2-四氢噻吩基 | 1 | |
6-66 | H | 2-吡咯基 | 1 | |
6-67 | H | 3-吡咯基 | 1 | |
6-68 | H | 4-吡咯基 | 1 | |
6-69 | H | 1-四唑基 | 1 | |
6-70 | H | 5-四唑基 | 1 | |
6-71 | H | 3-(1,2,4)-三唑基 | 1 | |
6-72 | H | 5-(1,2,4)-三唑基 | 1 | |
6-73 | CH3 | 2-噻吩基 | 1 | |
6-74 | CH2CH3 | 2-噻吩基 | 1 | |
6-75 | CH2CH2CH3 | 2-噻吩基 | 1 | |
6-76 | CH2CH2CH2CH3 | 2-噻吩基 | 1 | |
6-77 | CH2CHCH2 | 1-甲基-4-咪唑基 | 1 | |
6-78 | CH2CCH | 1-甲基-4-咪唑基 | 1 | |
6-79 | C(O)OCH3 | 1,3-二甲基-5-Cl-吡唑基 | 1 | |
6-80 | C(O)CH3 | 2,4-二甲基-5-噻唑基 | 1 | |
6-81 | CH2OCH3 | 5-(2-吡啶基)-2-噻吩基 | 1 | |
6-82 | CH2OCH2CH3 | 2-甲基-5-CF3-4-呋喃基 | 1 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃)/1H-NMR |
6-83 | CH2cPr | 2,5-二甲基-3-噻吩基 | 1 | |
6-84 | H | 2-Cl-5-吡啶基 | 1 | 2,64,d,3H,N-CH3 |
6-85 | H | 2-吡啶基 | 2 | |
6-86 | H | 3-吡啶基 | 2 | |
6-87 | H | 3-吡啶基 | 2 | |
6-88 | H | 4-吡啶基 | 2 | |
6-89 | H | 1-嘧啶基 | 2 | |
6-90 | H | 3-嘧啶基 | 2 | |
6-91 | H | 4-嘧啶基 | 2 | |
6-92 | H | 2-噻吩基 | 2 | |
6-93 | H | 3-噻吩基 | 2 | |
6-94 | H | 2-呋喃基 | 2 | |
6-95 | H | 3-呋喃基 | 2 | |
6-96 | H | 2-四氢呋喃基 | 2 | |
6-97 | H | 3-四氢呋喃基 | 2 | |
6-98 | H | 3-吡唑基 | 2 | |
6-99 | H | 4-吡唑基 | 2 | |
6-100 | H | 5-吡唑基 | 2 | |
6-101 | H | 2-咪唑基 | 2 | |
6-102 | H | 4-咪唑基 | 2 | |
6-103 | H | 5-咪唑基 | 2 | |
6-104 | H | 2-噻唑基 | 2 | |
6-105 | H | 4-噻唑基 | 2 | |
6-106 | H | 5-噻唑基 | 2 | |
6-107 | H | 2-四氢噻吩基 | 2 | |
6-108 | H | 2-吡咯基 | 2 | |
6-109 | H | 3-吡咯基 | 2 | |
6-110 | H | 4-吡咯基 | 2 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃)/1H-NMR |
6-111 | H | 1-四唑基 | 2 | |
6-112 | H | 5-四唑基 | 2 | |
6-113 | H | 3-(1,2,4)-三唑基 | 2 | |
6-114 | H | 5-(1,2,4)-三唑基 | 2 | |
6-115 | CH3 | 2-噻吩基 | 2 | |
6-116 | CH2CH3 | 2-噻吩基 | 2 | |
6-117 | CH2CH2CH3 | 2-噻吩基 | 2 | |
6-118 | CH2CH2CH2CH3 | 2-噻吩基 | 2 | |
6-119 | CH2CHCH2 | 1-甲基-4-咪唑基 | 2 | |
6-120 | CH2CCH | 1-甲基-4-咪唑基 | 2 | |
6-121 | C(O)OCH3 | 1,3-二甲基-5-Cl-吡唑基 | 2 | |
6-122 | C(O)CH3 | 2,4-二甲基-5-噻唑基 | 2 | |
6-123 | CH2OCH3 | 5-(2-吡啶基)-2-噻吩基 | 2 | |
6-124 | CH2OCH2CH3 | 2-甲基-5-CF3-4-呋喃基 | 2 | |
6-125 | CH2cPr | 2,5-二甲基-3-噻吩基 | 2 | |
6-126 | H | 2-Cl-5-吡啶基 | 2 | 2,65,d,3H,N-CH3 |
表7:式(Ib)化合物,其中R2=Cl;W=C-Cl;R3=R6=CF3;m=2;R4=Y=H;R5=CH3
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) |
7-1 | H | 2-吡啶基 | 0 | 油状 |
7-2 | H | 3-吡啶基 | 0 | |
7-3 | H | 3-吡啶基 | 0 | |
7-4 | H | 4-吡啶基 | 0 | |
7-5 | H | 1-嘧啶基 | 0 | |
7-6 | H | 3-嘧啶基 | 0 | |
7-7 | H | 4-嘧啶基 | 0 | |
7-8 | H | 2-噻吩基 | 0 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) | |
7-9 | H | 3-噻吩基 | 0 | ||
7-10 | H | 2-呋喃基 | 0 | ||
7-11 | H | 3-呋喃基 | 0 | ||
7-12 | H | 2-四氢呋喃基 | 0 | ||
7-13 | H | 3-四氢呋喃基 | 0 | ||
7-14 | H | 3-吡唑基 | 0 | ||
7-15 | H | 4-吡唑基 | 0 | ||
7-16 | H | 5-吡唑基 | 0 | ||
7-17 | H | 2-咪唑基 | 0 | ||
7-18 | H | 4-咪唑基 | 0 | ||
7-19 | H | 5-咪唑基 | 0 | ||
7-20 | H | 2-噻唑基 | 0 | ||
7-21 | H | 4-噻唑基 | 0 | ||
7-22 | H | 5-噻唑基 | 0 | ||
7-23 | H | 2-四氢噻吩基 | 0 | ||
7-24 | H | 2-吡咯基 | 0 | ||
7-25 | H | 3-吡咯基 | 0 | ||
7-26 | H | 4-吡咯基 | 0 | ||
7-27 | H | 1-四唑基 | 0 | ||
7-28 | H | 5-四唑基 | 0 | ||
7-29 | H | 3-(1,2,4)-三唑基 | 0 | ||
7-30 | H | 5-(1,2,4)-三唑基 | 0 | ||
7-31 | H | 2-噻吩基 | 0 | ||
7-32 | H | 2-噻吩基 | 0 | ||
7-33 | H | 2-噻吩基 | 0 | ||
7-34 | H | 2-噻吩基 | 0 | ||
7-35 | H | 1-甲基-4-咪唑基 | 0 | ||
7-36 | H | 1-甲基-4-咪唑基 | 0 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) | |
7-37 | H | 1,3-二甲基-5-Cl-吡唑基 | 0 | ||
7-38 | H | 2,4-二甲基-5-噻唑基 | 0 | ||
7-39 | H | 5-(2-吡啶基)-2-噻吩基 | 0 | ||
7-40 | H | 2-甲基-5-CF3-4-呋喃基 | 0 | ||
7-41 | H | 2,5-二甲基-3-噻吩基 | 0 | ||
7-42 | H | 2-Cl-5-吡啶基 | 0 | ||
7-43 | H | 2-吡啶基 | 1 | ||
7-44 | H | 3-吡啶基 | 1 | ||
7-45 | H | 3-吡啶基 | 1 | ||
7-46 | H | 4-吡啶基 | 1 | ||
7-47 | H | 1-嘧啶基 | 1 | ||
7-48 | H | 3-嘧啶基 | 1 | ||
7-49 | H | 4-嘧啶基 | 1 | ||
7-50 | H | 2-噻吩基 | 1 | ||
7-51 | H | 3-噻吩基 | 1 | ||
7-52 | H | 2-呋喃基 | 1 | ||
7-53 | H | 3-呋喃基 | 1 | ||
7-54 | H | 2-四氢呋喃基 | 1 | ||
7-55 | H | 3-四氢呋喃基 | 1 | ||
7-56 | H | 3-吡唑基 | 1 | ||
7-57 | H | 4-吡唑基 | 1 | ||
7-58 | H | 5-吡唑基 | 1 | ||
7-59 | H | 2-咪唑基 | 1 | ||
7-60 | H | 4-咪唑基 | 1 | ||
7-61 | H | 5-咪唑基 | 1 | ||
7-62 | H | 2-噻唑基 | 1 | ||
7-63 | H | 4-噻唑基 | 1 | ||
7-64 | H | 5-噻唑基 | 1 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) | |
7-65 | H | 2-四氢噻吩基 | 1 | ||
7-66 | H | 2-吡咯基 | 1 | ||
7-67 | H | 3-吡咯基 | 1 | ||
7-68 | H | 4-吡咯基 | 1 | ||
7-69 | H | 1-四唑基 | 1 | ||
7-70 | H | 5-四唑基 | 1 | ||
7-71 | H | 3-(1,2,4)-三唑基 | 1 | ||
7-72 | H | 5-(1,2,4)-三唑基 | 1 | ||
7-73 | H | 2-噻吩基 | 1 | ||
7-74 | H | 2-噻吩基 | 1 | ||
7-75 | H | 2-噻吩基 | 1 | ||
7-76 | H | 2-噻吩基 | 1 | ||
7-77 | H | 1-甲基-4-咪唑基 | 1 | ||
7-78 | H | 1-甲基-4-咪唑基 | 1 | ||
7-79 | H | 1,3-二甲基-5-Cl-吡唑基 | 1 | ||
7-80 | H | 2,4-二甲基-5-噻唑基 | 1 | ||
7-81 | H | 5-(2-吡啶基)-2-噻吩基 | 1 | ||
7-82 | H | 2-甲基-5-CF3-4-呋喃基 | 1 | ||
7-83 | H | 2,5-二甲基-3-硫代苯基 | 1 | ||
7-84 | H | 2-Cl-5-吡啶基 | 1 | ||
7-85 | H | 2-吡啶基 | 2 | ||
7-86 | H | 3-吡啶基 | 2 | ||
7-87 | H | 3-吡啶基 | 2 | ||
7-88 | H | 4-吡啶基 | 2 | ||
7-89 | H | 1-嘧啶基 | 2 | ||
7-90 | H | 3-嘧啶基 | 2 | ||
7-91 | H | 4-嘧啶基 | 2 | ||
7-92 | H | 2-噻吩基 | 2 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) | |
7-93 | H | 3-噻吩基 | 2 | ||
7-94 | H | 2-呋喃基 | 2 | ||
7-95 | H | 3-呋喃基 | 2 | ||
7-96 | H | 2-四氢呋喃基 | 2 | ||
7-97 | H | 3-四氢呋喃基 | 2 | ||
7-98 | H | 3-吡唑基 | 2 | ||
7-99 | H | 4-吡唑基 | 2 | ||
7-100 | H | 5-吡唑基 | 2 | ||
7-101 | H | 2-咪唑基 | 2 | ||
7-102 | H | 4-咪唑基 | 2 | ||
7-103 | H | 5-咪唑基 | 2 | ||
7-104 | H | 2-噻唑基 | 2 | ||
7-105 | H | 4-噻唑基 | 2 | ||
7-106 | H | 5-噻唑基 | 2 | ||
7-107 | H | 2-四氢噻吩基 | 2 | ||
7-108 | H | 2-吡咯基 | 2 | ||
7-109 | H | 3-吡咯基 | 2 | ||
7-110 | H | 4-吡咯基 | 2 | ||
7-111 | H | 1-四唑基 | 2 | ||
7-112 | H | 5-四唑基 | 2 | ||
7-113 | H | 3-(1,2,4)-三唑基 | 2 | ||
7-114 | H | 5-(1,2,4)-三唑基 | 2 | ||
7-115 | H | 2-噻吩基 | 2 | ||
7-116 | H | 2-噻吩基 | 2 | ||
7-117 | H | 2-噻吩基 | 2 | ||
7-118 | H | 2-噻吩基 | 2 | ||
7-119 | H | 1-甲基-4-咪唑基 | 2 | ||
7-120 | H | 1-甲基-4-咪唑基 | 2 |
化合物号 | X | R<sup>1</sup> | n | m.p.(℃) |
7-121 | H | 1,3-二甲基-5-Cl-吡唑基 | 2 | |
7-122 | H | 2,4-二甲基-5-噻唑基 | 2 | |
7-123 | H | 5-(2-吡啶基)-2-噻吩基 | 2 | |
7-124 | H | 2-甲基-5-CF3-4-呋喃基 | 2 | |
7-125 | H | 2,5-二甲基-3-噻吩基 | 2 | |
7-126 | H | 2-Cl-5-吡啶基 | 2 | |
7-127 | CH3 | 2-吡啶基 | 1 | 油状 |
7-128 | CH3 | 3-吡啶基 | 0 | |
7-129 | CH3 | 3-吡啶基 | 0 | |
7-130 | CH3 | 4-吡啶基 | 0 |
根据本发明的另一特征,提供了一种用于在某一场所控制害虫的方法,该方法包括施用有效量的式(I)化合物或其盐。对此,所述化合物通常以杀虫组合物形式(即,与适用于杀虫组合物的相容性稀释剂或载体和/或表面活性剂相联和)使用,例如以下文所述的形式。
下文所采用的术语“本发明化合物”包含如上所定义的式(I)的1-芳基-3偕胺肟-吡唑和其杀虫可接受的盐。
如上所述,本发明的一个方面是提供一种用于在某一场所控制害虫的方法。场所包括,例如害虫自身、害虫寄居或取食的地方(植物、大田、森林、果园、水道、土壤、植物产品等)、或将易受害虫侵害的地方。因此本发明化合物可直接施用至害虫、害虫寄居或取食的地方或将易受害虫侵害的地方。
如前述杀虫用途中明显表示的,本发明提供杀虫活性化合物和利用所述化合物控制许多害虫种类的方法,包括:节肢动物,尤其是昆虫或蜘蛛类动物如螨类,或蠕虫如植物线虫。因此本发明的化合物可有利地用于实际应用中,例如农业或园艺作物、林业、兽药或畜牧业或公共健康中。
例如本发明化合物可用于下列应用中和下列害虫上:
控制土壤昆虫,例如南瓜十二星叶甲、白蚁(尤其用于保护建筑物)、甘蓝种蝇蛆、切根虫、根象甲、普通蛀茎夜蛾、地老虎、根蚜或蛴螬。所述化合物也可用于提供活性以控制植物致病线虫,例如根瘤线虫、孢囊线虫、桑大型针线虫、枯斑线虫、或茎线虫或甘薯茎线虫,或控制螨类。对于控制土壤害虫,例如南瓜十二星叶甲,该化合物有利地以有效量施用于或混入土壤中,在所述土壤中种植有作物、或将种植或播种、或生长有植物根系。
在公共健康领域,该化合物优选用于控制许多昆虫,尤其是垃圾苍蝇或其它双翅目害虫,例如家蝇、厩蝇、水虻、角蝇、鹿虻、马蝇、摇蚊、蠓、墨蚊或蚊子。
在保护储藏产品中,例如谷类,包括谷粒或面粉、落花生、动物饲料、木材或家庭用品如地毯和纺织品,本发明的化合物有利地控制节肢动物,更尤其是甲虫包括象鼻虫、蛾或螨类例如粉斑螟属(粉螟)、圆皮蠹属(小圆皮蠹)、拟谷盗属(粉甲虫)、谷象属(谷类象鼻虫)或粉螨属(螨)的侵袭。
控制侵害家庭或工业房屋的蟑螂、蚂蚁或白蚁或类似节肢动物害虫,或控制水道、井、水库或其它流动或静止水中的蚊子幼虫。
以防止白蚁(例如散白蚁属、异白蚁属、乳白蚁属)侵袭建筑物的方式处理地基、建筑物或土壤。
在农业中控制鳞翅目(蝴蝶和蛾)的成虫、幼虫和卵,例如实夜蛾属如Heliothis virescens(烟芽夜蛾)、棉铃虫和Heliothis zea。控制鞘翅目(甲虫)的成虫和幼虫,例如花象属如棉铃象(棉铃象甲)、Leptinotarsa decemlineata(马铃薯叶甲)、Diabrotica spp.(南瓜十二星叶甲)。控制异翅目(半翅目和同翅目),例如木虱属、粉虱、粉虱属、蚜属、瘤蚜属、巢菜修尾蚜、山核桃根瘤蚜属、Nephotettix spp.(黑尾叶蝉)、褐飞虱属。
控制双翅目,例如家蝇属。控制缨翅目如烟蓟马。
控制直翅目,例如飞蝗属和沙漠蝗属(蝗虫和蟋蟀)如蟋蟀属和Acheta spp.例如东方蜚蠊、美洲大蠊、德国小蠊、非洲飞蝗和沙漠蝗。控制弹尾目,例如大蠊属和小蠊属(蜚蠊)。
控制农业上重要的节肢动物,例如粉螨(螨类)如叶螨属和全爪螨属。
控制以直接或通过传播植物细菌性、病毒性、支原质体或真菌病害侵袭农业、林业或园艺上重要的植物或树木的线虫。例如根结线虫如根结线虫属(如南方根结线虫)。
在兽医学或畜牧业领域、或维持公共健康中控制节肢动物,所述节肢动物内寄生或外寄生于脊椎动物,尤其是温血脊椎动物,例如家畜如牛、羊、山羊、马、猪、家禽、狗或猫,例如蜱螨目,包括扁虱(如软体扁虱(sot-bodied ticks)包括软蜱科如隐喙蜱属和钝缘蜱属(例如非洲钝缘蜱属);硬体扁虱(hard-bodied ticks)包括硬蜱科如牛蜱属如微小牛蜱、扇头蜱属如非洲扇头蜱和血红扇头蜱;螨类(例如畜虱属);跳蚤(如栉首蚤属如Ctenocephalides felis(猫栉首蚤)和Ctenocephalides canis(犬栉首蚤属));虱子如毛羽虱属;双翅目(伊蚊属、按蚊属、家蝇属、皮蝇属);半翅目;网翅目(如大蠊属、小蠊属);膜翅目;例如控制由植物线虫(例如Trichostrongylidae科的线虫)引起的消化道侵染。
本发明的一个优选方面,式(I)化合物用于控制动物寄生虫。待处理的动物优选为家庭伙伴动物如狗或猫。
本发明的另一方面,式(I)化合物或其盐或组合物用于制备兽药。
在用于控制节肢动物,尤其是昆虫或蜘蛛类动物如螨类,或蠕虫如植物线虫的实际应用中,一种方法,例如包括将有效量的本发明化合物施用于植物或其生长介质上。对于该方法,通常以每公顷处理场所约2g至约1kg的活性化合物的有效量范围,将本发明化合物施用至节肢动物或线虫侵袭的场所。理想的条件下,根据所控制的害虫,更低的用量可提供足够的保护。另一方面,不利的天气条件、害虫的抗性或其它因素可能需要使用更高用量的活性成分。最佳用量通常取决于影响因素的多少,例如待控制的害虫的种类、受侵害植物的种类或生长期、行距或者施用方法。优选地,活性化合物的有效量范围为约10g/ha至400g/ha,更优选约50g/ha至约200g/ha。
当害虫是土壤传播的,通常以任何常规方式,将活性化合物以配制的组合物均匀分布在待处理区域上(例如撒播或带状处理),并且以约10g/ha至约400g ai/ha,优选约50g/ha至约200g ai/ha的比率施用。当以根浸幼苗或滴灌植物方式进行施用时,液剂或悬浮剂包含约0.075至约1000mg ai/l,优选约25至约200mg ai/l。视需要,通常施用于大田或作物的生长区域,或施用于待保护以免受侵袭的种子或植物的附近。本发明化合物可通过在整片区域上用水喷洒洗涤进入土壤中,或可通过雨水的天然作用而进入土壤。施用中或施用后,配制的化合物可视需要以机械方式分布到土壤中,例如通过耕作、耙地或使用牵引覆土链。施用可在种植前、种植中、种植后,但在已开始萌芽前或萌芽后进行。
本发明化合物和用其控制害虫的方法在保护大田、草料、耕地、温室、果园或葡萄园作物,观赏植物或种植或森林树木方面特别有价值,例如:谷类(如小麦或水稻)、棉花、蔬菜(如花椒)、大田作物(如甜菜、大豆或油菜)、草地或草料作物(如玉米或高梁)、果园或树丛(如坚果或纹孔场(pit fruit)或柑橘)、或玻璃温室下、花园或公园中的观赏植物、花或蔬菜或灌木,或森林中、种植园中或苗圃中的林木(落叶的和常绿的)。
本发明化合物在保护木材(未伐的(standing)、采伐的、改装的、储藏的或建筑的)免受如叶蜂或甲虫或白蚁的侵袭方面也是颇有价值的。
无论是整个地、经研磨还是经混合进入产品中,本发明化合物应用于保护储藏产品如谷物、水果、坚果、香料或烟草免受蛾、甲虫、螨或谷类象鼻虫的侵袭。也保护天然或改造形式(如地毯或纺织品)的储藏动物产品例如皮肤、毛发、羊毛或羽毛免受蛾或甲虫侵袭,以及保护储藏的肉、鱼或谷物免受甲虫、螨或苍蝇的侵袭。
此外,本发明组合物及其使用方法在控制有害的、或传播家畜疾病或作为家畜疾病的传播载体的节肢动物或蠕虫尤其有价值,例如那些上文所提及的,更优选控制扁虱、螨、白虱、跳蚤、摇蚊、或叮咬、讨厌的或蝇蛆病苍蝇。本发明化合物优选用于控制存在于家畜寄主动物体内或在皮肤内或皮肤上取食或吸取家畜血液的节肢动物或蠕虫,对此目的该化合物可以是口服、非肠道、经皮或局部施用的。
通常来说,下文所述的用于施用至生长作物或作物生长区域或用作拌种的组合物可选地用于保护储藏产品、家庭用品、常规环境的特性或区域。适宜的施用本发明化合物的方法包括:将粉剂、颗粒剂、烟雾剂或泡沫剂,或细碎的悬浮剂或胶囊化的组合物以叶面喷洒(例如以犁沟喷洒)的方式,或通过浸渍将粉剂、颗粒剂、烟剂或泡沫剂以土壤或根部处理的方式施用至生长作物;采用液浆或粉剂以拌种施用至作物种子;
通过非肠道、口服或局部施用组合物至经节肢动物或蠕虫侵害或暴露于节肢动物或蠕虫侵害处的动物,该组合物中的在一段时间内活性成分显示立即的和/或延长的控制节肢动物或蠕虫的作用,例如通过掺入食物或适宜的口服药物制剂、可食用的诱饵、盐砖、饮食补充物、倾泻制剂(pour-on formulation)、喷雾剂、浴液、浸液(dips)、淋浴液(showers)、喷射液(jets)、粉剂、油脂、洗发剂、乳膏、蜡涂或家畜自身处理系统;
将本发明化合物以喷雾剂、雾剂、粉剂、烟剂、蜡涂、刷涂、颗粒剂或饵剂,或以滴入至水道、井、水库或其它流动或静止的水中的方式,施用至害虫可能潜伏的常规环境或特定位置,包括储藏产品、木材、家庭用品,或家庭或工业房屋。
当口服施用时,式(I)化合物尤其有利地控制动物寄生虫,在本发明的进一步优选的方面,式(I)化合物通过口服施用用于控制动物寄生虫。式(I)化合物或其盐可以在在进食前、进食期间或进食后施用。式(I)化合物或其盐可以与载体和/或食品混合。
以剂量范围为0.1至500mg/kg的式(I)化合物或其盐/动物体重千克(mg/kg),将式(I)化合物或其盐口服施用至动物。
用式(I)化合物或其盐处理动物,优选处理家畜的频率通常为约每周1次至每年1次,优选为约每两周1次至每三个月1次。
本发明化合物与另一种杀寄生虫有效物质一起施用是最有利的,例如内杀寄生虫剂,和/或外杀寄生虫剂,和/或内外杀寄生虫剂。例如这样的化合物包括大环内酯类如阿维菌素类,或米尔倍霉素类如伊维菌素、pyratel,或昆虫生长调节剂如虱螨脲或烯虫酯。
式(I)化合物也可用于控制已知经基因工程改良的作物或正待进行基因工程改良的作物中的害虫。通常转基因植物以特别有利的特性而著称,例如对于某些作物保护剂的耐受性、对于植物疾病或植物疾病病原物的抵抗力,例如某些昆虫或微生物如真菌、细菌或病毒。其它特别的特性涉及例如收成物的量、品质、储藏期、组成和特定成分。因此已知一些转基因植物可提高淀粉含量或改良淀粉品质,或收成物具有不同的脂肪酸组成。
用于具经济重要性的转基因有用作物和观赏植物中是优选的,例如谷物(如小麦、大麦、裸麦、燕麦、高梁、水稻、木薯和玉米)或其它的甜菜、棉花、大豆、油菜、马铃薯、西红柿、豌豆和其它蔬菜种类的作物。
当用于转基因作物时,尤其是那些具有昆虫抗性的作物,除了在其它作物中观察到的抗害虫的效果外,还常常观察到对于在所述转基因作物中施用特殊的效果,例如改良的或特别扩展的可控制害虫谱,可用于施用的改善的施用量。
因此本发明还提供式(I)的化合物用于在转基因农作植物中控制害虫的用途。
另一方面,本发明提供一种包含一种或多种上述定义的本发明化合物的杀虫组合物,与之相结合的是,优选均匀分散在一种或多种相容的杀虫可接受的稀释剂或载体和/或表面活性剂[即适用于杀虫组合物的本领域通常可接受的稀释剂或载体和/或表面活性剂类型并与本发明的化合物相容]。
实践中,本发明的化合物大多形成组合物的一部分。该组合物可用于控制节肢动物,尤其是昆虫和蜘蛛类动物(如螨类),或蠕虫如植物线虫。该组合物可以本领域任何已知的适宜方式,施用于在任何房屋中的所述害虫或室内或室外区域。该组合物包含至少一种本发明化合物作为活性成分,其与一种或多种其它相容的成分相组合或联合,例如固体或液体载体或稀释剂、助剂、表面活性剂等适合于使用目的的添加剂,并且所述相容性成分是农艺学或药学上可接受的。可以任何本领域已知的方法加以制备的该组合物同样是本发明的一部分。
本发明的化合物,以其可商购可得的制剂和以该制剂所制备的使用形式,可与其它活性成分相混合,例如杀虫剂、引诱剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节物质或除草剂。
杀虫剂包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、甲脒类、锡化合物和微生物产生的物质:
混合物中优选的组分为
1.来自磷化合物组
乙酰甲胺磷、甲基吡噁磷、益棉磷、保棉磷、溴硫磷、乙基溴硫磷、硫线磷(F-67825)、氯乙氧磷(chlorethoxyphos)、毒虫畏、氯甲硫磷、毒死蜱、甲基毒死蜱、内吸磷、甲基内吸磷、砜吸磷、氯亚胺硫磷、二嗪磷、敌敌畏、百治磷、乐果、乙拌磷、苯硫磷、乙硫磷、灭线磷、乙嘧硫磷、伐灭磷、虫胺磷、杀螟硫磷、线虫磷、吡氟硫磷、倍硫磷、地虫硫磷、安果、噻唑磷、庚烯磷、氯唑磷、异拌磷、噁唑磷、马拉硫磷、虫螨畏、甲胺磷、杀扑磷、蔬果磷、速灭磷、久效磷、二溴磷、氧乐果、亚砜吸磷、对硫磷、甲基对硫磷、稻丰散、甲拌磷、伏杀硫磷、硫环磷、磷虫威(BAS-301)、亚胺硫磷、磷胺、辛硫磷、嘧啶磷、乙基嘧啶磷、甲基嘧啶磷、丙溴磷、丙虫磷、胺丙畏、丙硫磷、吡唑硫磷、哒嗪硫磷、喹硫磷、甲丙硫磷、双硫磷、特丁磷、丁基嘧啶磷、杀虫畏、二甲硫吸磷、三唑磷、敌百虫、蚜灭多;
2.来自氨基甲酸酯组
棉铃威(OK-135)、涕灭威、仲丁威(BPMC)、甲萘威、克百威、丁硫克百威(Carbosulfan)、除线威(Cloethocarb)、丙硫克百威、乙硫苯威(Ethiofencarb)、呋线威(Furathiocarb)、HCN-801、叶蝉散、灭多威、5-甲基-间异丙苯基丁酰基(甲基)氨基甲酸酯(5-methyl-m-cumenylbutyryl(methyl)carbamate)、杀线威、抗蚜威、残杀威、硫双威、久效威(thiofanox)、1-甲硫基(亚乙基氨基)-N-甲基-N-(吗啉基硫代)氨基甲酸酯(UC 51717)、唑蚜威;
3.来自羧酸酯组
氟酯菊酯、烯丙菊酯、顺式氯氰菊酯、(E)-(1R)-顺式-2,2-二甲基-3-(2-氧代硫杂环戊烷-3-亚基甲基)环丙烷羧酸5-苄基-3-呋喃甲酯、β-氟氯氰菊酯、α-氯氰菊酯、β-氯氰菊酯、生物烯丙菊酯、生物烯丙菊酯((S)-环戊基异构体)、生物苄呋菊酯、氟氯菊酯、(1RS)-反式-3-(4-叔丁苯基)-2,2-二甲基环丙烷羧酸(RS)-1-氰基-1-(6-苯氧基-2-吡啶基)甲酯(NCI 85193)、乙氰菊酯、氰氟菊酯、氯氟氰菊酯、氟氰戊菊酯、氯氰菊酯、苯醚氰菊酯、溴氰菊酯、烯炔菊酯、高氰戊菊酯、五氟苯菊酯、甲氰菊酯、氰戊菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯(D异构体)、咪炔菊酯(S-41311)、氯氟氰菊酯、氯菊酯、苯氧菊酯((R)异构体)、炔酮菊酯、除虫菊酯(天然产物)、苄呋菊酯、七氟菊酯、胺菊酯、θ-氯氰菊酯、四溴菊酯,四氟苯菊酯、ζ-氯氰菊酯(F-56701);
4.来自脒组
双虫脒、杀虫脒;
5.来自锡化合物组
三环锡、苯丁锡;
6.其它
阿维菌素、ABG-9008、啶虫脒、灭螨醌、Anagrapha falcitera、AKD-1022、AKD-3059、环虫酰肼(ANS-118)、印楝素、苏云金杆菌、Beauveria bassianea、杀虫磺、联苯肼酯、乐杀螨、BJL-932、溴螨酯、BTG-504、BTG-505、噻嗪酮、毒杀芬、杀螟丹、乙酯杀螨醇、溴虫腈、定虫隆、2-(4-氯苯基)-4,5-二苯基噻吩(苯塞螨UBI-T 930)、chlorfentezine、chlorproxyfen、环虫酰肼、clothianidine、2-萘甲基环丙烷羧酸酯(Ro12-0470)、灭蝇胺、噻虫嗪(diacloden)、丁醚脲、DBI-3204、2-氯-N-(3,5-二氯-4-(1,1,2,3,3,3-六氟-1-丙氧基)苯基)氨基甲酰基)-2-甲亚胺酸乙酯、滴滴涕、三氯杀螨醇、除虫脲、N-(2,3-二氢-3-甲基-1,3-噻唑-2-亚基)-2,4-二甲苯胺、二羟甲基二羟基吡咯烷、消螨通、二硝酯、苯虫醚、埃玛菌素-苯甲酸酯、硫丹、ethiprole(sulfethiprole)、醚菊酯、乙螨唑、喹螨醚、双氧威、氟虫腈、啶蜱脲(fluazuron)、氯螨嗪(Flufenzine,SZI-121)、2-氟-5-(4-(4-乙氧苯基)-4-甲基-1-戊基)二苯醚(MTI 800)、颗粒层增殖及核型多角体病病毒(Granulosis and nuclear polyhedrosis viruses)、唑螨酯、Fenthiocarb、嘧螨酯、氟螨噻、flubrocythrinate、氟螨脲、氟虫脲、flufenzine、三氟醚菊酯、fluproxyfen、林丹、氯虫酰肼、溴氟醚菊酯(halofenprox)、氟铃脲(DE_473)、噻螨酮、HOI-9004、伏蚁腙(AC 217300)、IKI-220、茚虫威、齐墩螨素、L-14165、吡虫啉、噁二唑虫(DPX-MP062)、kanemite(AKD-2023)、虱螨脲、M-020、甲氧虫酰肼、弥拜菌素、NC-196、neemgard、呋虫胺、烯啶虫胺、2-硝甲基-4,5-二氢-6H-噻嗪(DS 52618)、2-硝甲基-3,4-二氢噻唑(SD35651)、2-硝基亚甲基-1,2-噻嗪-3-基氨基甲酸醛(噻虫醛(WL108477))、氟酰脲、pirydaryl、炔螨特、protrifenbute、吡蚜酮、哒螨灵、嘧螨醚、吡丙醚、NC-196、NC-1111、NNI-9768、氟酰脲(MCW-275)、OK-9701、吲哚酯(OK-9601)、OK-9602、OK-9802、R-195、RH-0345、RH-2485、RYI-210、S-1283、S-1833、SI-8601、氟硅菊酯、Silomadine(CG-177)、多杀菌素、spirodiclofen、SU-9118、虫酰肼、吡螨胺、伏虫隆、三氯杀螨砜、杀螨硫醚、噻虫啉、噻虫啉、杀虫环、噻虫嗪、唑虫酰胺、唑蚜威、triethoxyspinosyn A、杀虫隆、增效炔醚、vertalec(mykotal)、YI-5301。
上述用于组合的成分是已知的活性成分,大多描述于Ch.RWorthing,S.B.Walker,The Pesticid Manual(农药手册),第12版,British Crop Protection Council,Farnham 2000中。
用于本发明的化合物的有效用量可在很大范围内变化,尤其取决于待消灭的害虫种类或侵害程度,例如害虫侵害作物的程度。通常来说,本发明组合物一般包含约0.05至约95%(按重量计)的一种或多种本发明的活性成分、约1至约95%的一种或多种固体或液体载体,并且任选地约0.1至约50%的一种或多种其它相容的组分,例如表面活性剂等。本说明书中,术语“载体”指有机或无机的、天然或合成的、与活性成分结合改善其施用(例如施用至植物、种子或土壤)的成分。因而该载体通常是惰性的,并且必须是可接受的(例如农艺学可接受的,尤其对于所处理的植物)。
载体可为固体的,例如粘土、天然或合成的硅酸盐、二氧化硅、树脂、蜡、固态肥料(例如铵盐)、地面天然矿物质(如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石、膨润土或硅藻土),或地面合成矿物质(如二氧化硅、氧化铝或硅酸盐,尤其是硅酸铝或硅酸镁)。如下为适用于颗粒的固体载体:碾碎的或分级的天然岩石如方解石、大理石、浮石、海泡石和白云石;无机或有机粉状的合成颗粒;有机物质颗粒如锯屑、椰子壳、玉米芯、玉米壳或烟草杆;硅藻土、磷酸三钙、粉状的软木、或吸收的炭黑;水溶性聚合物、树脂、蜡;或固体肥料。这类固体组合物可视需要含有一种或多种相容的湿润剂、分散剂、乳化剂或着色剂,当为固态时,也可用作稀释剂。
载体也可为液态,例如:水;醇类,尤其是丁醇或乙二醇,以及它们的醚或酯,优选乙二醇一甲醚乙酸酯;酮类,优选丙酮、环己酮、甲基乙基酮、甲基异丁基酮或异佛尔酮;石油馏分如链烷烃族的或芳族烃,尤其是二甲苯或烷基萘;矿物或植物油;脂肪族氯代烃,尤其是三氯乙烷或二氯甲烷;芳族氯代烃,尤其是氯苯;水溶性或强极性溶剂如二甲基甲酰胺、二甲亚砜或N-甲基吡咯烷酮;液化气等,或它们的混合物。
表面活性剂可为离子或非离子类型的乳化剂、分散剂或湿润剂,或这类表面活性剂的混合物。例如聚丙烯酸盐、木质磺酸盐、苯酚磺酸或萘磺酸盐、环氧乙烷与脂肪醇或脂肪酸或脂肪酯或脂肪胺的缩聚物、经取代的苯酚(尤其是烷基苯酚或芳基苯酚)、硫代琥珀酸酯的盐类、牛磺酸衍生物(尤其是烷基牛磺酸酯)、醇类或环氧乙烷与苯酚缩聚物的磷酸酯、脂肪酸与多元醇的酯或上述化合物的硫酸酯、磺酸酯或硫酸酯官能衍生物。
当活性成分和/或惰性载体仅为水微溶或水不可溶,以及施用组合物的载体为水时,通常必须含有至少一种表面活性剂。
本发明组合物可进一步含有其它添加剂如粘合剂或着色剂。粘合剂如羧甲基纤维素,或以粉末、颗粒或网格(lattices)形式的天然或合成聚合物,例如阿拉伯树胶、聚乙烯醇或聚乙酸乙烯酯,天然磷脂,如脑磷脂或卵磷脂,或合成磷脂可用于制剂中。可使用着色剂如无机色素,例如氧化铁、氧化钛或普鲁士蓝;有机染料如茜素染料、偶氮染料或金属酞花青染料;或微量营养物如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐或锌盐。
因而对于农业施用来说,本发明化合物通常以各种固体或液体形式的组合物形式存在。
可使用的固体组合物形式为粉剂(具有本发明化合物含量高至80%)、可湿性粉剂或颗粒剂(包括水分散粒剂),尤其是通过挤出、压制、浸渍颗粒载体所获得的、或从粉末开始进行粒化(在该可湿性粉剂或颗粒剂中,本发明化合物的含量介于约0.5至约80%之间)。包含一种或多种本发明化合物的固体状的均一或不均一的组合物,例如颗粒剂、丸剂、团块剂或胶囊剂,可用于在一段时间内处理静止或流动的水。利用滴流或间歇进料上述的水分散浓缩物可获得类似效果。
液态组合物,例如包括含水的或不含水的液剂或悬浮剂(如乳油、水乳剂、漂浮剂(flowables)、分散剂或液剂)或气雾剂。液体组合物也尤其包括乳油、分散剂、水乳剂、漂浮剂、气雾剂、可湿性粉剂(或喷粉剂)、干漂浮剂或膏剂,当施用时,组合物是液态或趋向于形成液态组合物的形式,例如以水喷雾剂(包括低量或超低量)或以雾剂或气雾剂形式。
液态组合物,例如以乳油或可溶性浓缩物的形式大多通常含有约5至约80重量%的活性成分,然而在实际中,准备用于施用的水乳剂或液剂包含约0.01至约20%的活性成分。除溶剂外,乳油或可溶性浓缩物可视需要含有约2至约50%的合适的添加物,例如稳定剂、表面活性剂、渗透剂、防腐剂、着色剂或粘合剂。通过用水稀释这些浓缩物,可获得特别适合施用于例如植物的任何所需浓度的水乳剂。这些组合物包括在本发明可使用的组合物范围中。水乳剂可以油包水或水包油的形式,并且它们具有高浓度。
除正常的农业施用外,本发明液态组合物可用于例如处理基质或受到节肢动物(或其它由本发明化合物控制的害虫)的侵害场所或易受侵害的场所,包括房屋、室外或室内储藏或加工区域、容器或装置,或静止或流动的水。
所有这些含水的分散剂或水乳剂或喷雾混合物可通过任何适宜方法施用至例如作物,主要通过喷雾的方式,通常以约100至约1,200升的喷雾混合物/公顷的量施用,但根据需要或施用技术可更高或更低(如低量或超低量)。本发明化合物或组合物便利地施用至植物,并且尤其是有待消灭害虫的根部或叶片。本发明化合物或组合物的另一个施用方法是通过化学灌溉(chemigation),也就是说,加入含有活性成分的制剂到灌溉水中。对于叶面杀虫剂该灌溉可洒水灌溉,或对于土壤或内吸性杀虫剂可地表灌溉或地下灌溉。
制备可用于喷雾的浓缩悬浮剂,使得产生稳定的没有沉淀(细磨)的液态产品,该浓缩悬浮剂通常含有约10至约75重量%的活性成分、约0.5至约30%的表面活性剂、约0.1至约10%的触变剂、约0至约30的适合添加剂如防泡剂、防腐剂、稳定剂、渗透剂、粘合剂,以及作为载体的水或无机液体(其中活性成分微溶或不溶)。一些有机或无机盐可溶解于载体中帮助防止沉淀或用作水的防冻剂。
通常制备的可湿性粉剂(或喷粉剂)含有约10至约80重量%的活性成分、约20至约90%的固体载体、约0至约5%的湿润剂、约3至约10%的分散剂,并且视需要含有约0至约80%的一种或多种稳定剂和/或其它添加剂如渗透剂、粘合剂、抗结块剂、着色剂等。为得到该可湿性粉剂,在适宜的搅拌机中,将活性成分与添加物质完全混合,这些添加的物质可注入多孔填充物中并用研磨机或其它适合的研磨工具研磨。这样所得到的可湿性粉剂的润湿性和悬浮性是有利的。它们可悬浮在水中以获得任何所需的浓度,并且使用该悬浮剂非常有利,尤其施用至植物叶片。
“水分散粒剂(WG)”(容易分散在水中的颗粒)是基本上接近于可湿性粉剂的组合物。可通过将上述可湿性粉剂颗粒化、或通过湿法(将细碎的活性成分与惰性填充物和微量水,如1至20重量%,或与粘合剂或分散剂的水溶液相接触,随后干燥并过筛)或通过干法(磨碎并过筛后压制)制备。
配制组合物的量和浓度可根据施用方法或组合物性质或其使用有所不同。通常来说,用于控制节肢动物或植物线虫的组合物含有约0.00001重量%至约95重量%,更优选约0.0005重量%至约50重量%的一种或多种本发明化合物,或总的活性成分(即本发明化合物与其它对节肢动物或植物线虫有毒的物质、增效剂、微量元素或稳定剂的总量)。将由农场主、养畜者、开业医生或开业兽医、害虫控制者或其它本领域技术人员对实际使用的组合物和施用量进行选择,以达到所需效果。
局部施用于动物、木材、储藏产品或家庭用品的固体或液体组合物通常含有约0.00005重量%至约90重量%,更优选约0.001重量%至约10重量%的一种或多种本发明化合物。对于动物口服或非肠道给药,包括经皮的固体或液体组合物,它们通常含有约0.1重量%至约90重量%的一种或多种本发明化合物。
加药饲料通常含有约0.001重量%至约3重量%的一种或多种本发明化合物。与饲料混合的浓缩物或添加物通常含有约5重量%至约90重量%,优选约5重量%至约50重量%的一种或多种本发明化合物。矿物盐砖(mineral salt licks)通常含有约0.1重量%至约10重量%的一种或多种式(I)化合物或其杀虫可接受的盐。
施用至家畜、货物、房屋或室外区域的粉剂或液体组合物可含有约0.0001重量%至约15重量%,更优选约0.005重量%至约2.0重量%的一种或多种本发明化合物。
处理水的适宜浓度介于约0.0001ppm和约20ppm之间,更优选约0.001ppm至约5.0ppm的一种或多种本发明化合物,并且采用适当的曝露持续时间可治疗性地用于鱼类养殖中。可食用的诱饵可含有约0.01重量%至约5重量%,优选约0.01重量%至约1.0重量%的一种或多种本发明化合物。
当非肠道、口服或经皮或其它方式施用给脊椎动物时,本发明化合物的剂量将取决于脊椎动物的种类、龄期或健康状态,并且取决于由节肢动物或蠕虫害虫的种类和其作用的程度或潜在的侵害。对于持续的药物,通过口服或肠胃外给药,单次剂量约0.1至100mg,优选约2.0至约20.0mg/kg的动物体重,或每天每kg的动物体重的剂量为约0.01至约20.0mg,优选约0.1至约5.0mg。通过利用持续释放制剂或装置,可合并几个月内每天的所需剂量,并且一次投药给动物。
下面的组合物实施例2A-2M说明用于控制节肢动物,尤其是用于螨类或昆虫,或植物线虫的组合物,其包含作为活性成分的本发明化合物,如制备实施例中所述的化合物。描述于实施例2A-2M中的组合物均可稀释,以获得用于大田中的适宜浓度的可喷洒组合物。用于下列组合物实施例2A-2M中的成分的一般化学描述(下列所有百分比均为重量百分比)如下所示:
商品名 化学描述
Ethylan BCP 壬基苯酚环氧乙烷缩合物
Soprophor BSU 三苯乙烯基苯酚环氧乙烷缩合物
Arylan CA 70%w/v的十二烷基苯磺酸钙
Solvesso 150 轻质C10芳族溶剂
Arylan S 十二烷基苯磺酸钠
Darvan NO2 木质素磺酸钠
Celite PF 合成的硅酸镁载体
Sopropon T36 聚羧酸钠盐
Rhodigel 23 多糖黄原胶
Bentone 38 镁蒙脱石的有机衍生物
Aerosil 细微的二氧化硅
实施例2A
用如下组分制备水溶性浓缩物:
活性成分 7%
Ethylan BCP 10%
N-甲基吡咯烷酮 83%
伴随着加热和搅拌,向部分溶解于N-甲基吡咯烷酮的EthylanBCP溶液加入活性成分,直至溶解。所得溶液用剩余溶剂定容。
实施例2B
用如下组分制备乳油(EC):
活性成分 25%(最大)
Soprophor BSU 10%
Arylan CA 5%
N-甲基吡咯烷酮 50%
Solvesso 150 10%
将前面三个组分溶于N-甲基吡咯烷酮中,然后将Solvesso 150加至其中,得到最终体积。
实施例2C
用如下组分制备可湿性粉剂(WP):
活性成分 40%
Arylan S 2%
Darvan NO2 5%
Celite PF 53%
将上述成分混合并在锤磨机中研磨至低于50微米粒度的粉末。
实施例2D
用如下组分制备含水漂浮制剂:
活性成分 40.00%
Ethylan BCP 1.00%
Sopropon T360. 0.20%
乙二醇 5.00%
Rhodigel 230. 0.15%
水 53.65%
将上述成分充分混合并且在球磨机中研磨,直到所获得的平均粒度低于3微米。
实施例2E
用如下组分制备可乳化的悬浮浓缩物:
活性成分 30.0%
Ethylan BCP 10.0%
Bentone 38 0.5%
Solvesso 150 59.5%
将上述成分充分混合并在球磨机中研磨,直到所获得的平均粒度低于3微米。
实施例2F
用如下组分制备水分散粒剂:
活性成分 30%
Darvan No 2 15%
Arylan S 8%
Celite PF 47%
将上述成分混合,在气流粉碎机中微粉化,并且随后在旋转造粒机中通过用水喷雾粒化(高至10%)。所得颗粒在流化床干燥器上干燥以除去多余的水。
实施例2G
用如下组分制备粉剂:
活性成分 1至10%
超细滑石粉末 99至90%
将上述成分充分混合并且视需要进一步研磨以获得更细的粉末。该粉末可施用于节肢动物侵害场所,例如垃圾场、储藏产品或家庭用品,或由节肢动物所侵害的或处于侵害危险中的动物,以通过经口摄取控制节肢动物。用于将粉剂分布于节肢动物侵害场所的适宜装置包括机械鼓风机、手摇抖动器或家畜自身处理装置。
实施例2H
用如下组分制备可食用饵剂:
活性成分 0.1至1.0%
小麦面粉 80%
糖浆 19.9至19%
将上述成分充分混合并且制成所需的饵剂形式。该可食用的饵剂可分布于受到节肢动物(例如蚂蚁、蝗虫、蟑螂或苍蝇)侵害的场所,例如家庭或工业房屋,如厨房、医院或储藏室或室外区域,以通过经口摄取控制节肢动物。
实施例2I
用如下组分制备液剂:
活性成分 15%
二甲亚砜 85%
将活性成分搅拌溶解在二甲亚砜中,并视需要加热。该溶液可以以注入施用(pour-on application)的方式经皮施用至被节肢动物侵害的家畜,或在透过聚四氟乙烯膜(0.22微米的孔径大小)的过滤杀菌后,通过非肠道注射,以施用量为1.2至12ml溶液/100kg动物体重进行施用。
实施例2J
用如下组分制备可湿性粉剂:
活性成分 50%
Ethylan BCP 5%
Aerosil 5%
Celite PF 40%
将Ethylan BCP吸附在Aerosil上,随后用其它成分混合并在锤磨机中研磨以得到可湿性粉剂,该可湿性粉剂可用水稀释至浓度为0.001%至2重量%的活性化合物,并且通过喷雾施用至被节肢动物(例如双翅类幼虫或植物线虫)侵害的场所,或通过喷雾或浸涂、或通过饮用水口服给药施用至由节肢动物侵害的或处于侵害危险中的家畜,以控制节肢动物。
实施例2K
由颗粒剂形成的缓释丸剂根据需要含有不同百分比的下列组分(类似于如前述的组合物):
活性成分
增稠剂
缓释剂
粘合剂
将充分混合的上述组分成形加工成颗粒,该颗粒压制成比重为2或更高的丸剂。该丸剂可以口服给药至反刍家畜以保留在瘤网胃中,使得在长时间内连续缓慢释放活性化合物,以控制由节肢动物对反刍家畜的侵害。
实施例2L
以颗粒剂、丸剂、块剂等形式的缓释组合物可由下列组分制得:
活性成分 0.5至25%
聚氯乙烯 75至99.5%
二辛基邻苯二甲酸至酯(增塑剂)
将上述组分混合并且随后通过熔体挤出或模塑法形成适宜的形状。例如该组合物用于加入静止水或装入与家畜相连的颈圈或耳标,通过缓慢释放控制害虫。
实施例2M
用如下组分制备水分散粒剂:
活性成分 85%(最大)
聚乙烯吡咯烷酮 5%
硅镁土 6%
十二烷基硫酸钠 2%
甘油 2%
将上述组分用水混合成45%的浆料,并且湿磨成颗粒大小为4微米,随后喷雾干燥除去水。
杀虫应用方法
利用本发明化合物进行下面有代表性的试验,以测定本发明化合物的杀寄生虫和杀虫活性。
方法A:筛选法,测定本发明化合物控制Ctenocephalides felis(猫栉首蚤)的系统效果
测试容器装有10头猫栉首蚤成虫。将玻璃圆柱体用石蜡密封一端,并且置于测试容器顶部。随后将测试化合物溶液移入牛血中,并且加至玻璃圆柱体中。将待测的猫栉首蚤保持在该人工狗试验中(血37℃,40-60%相对湿度;猫栉首蚤20-22℃,40-60%相对湿度),并且施用后24和48小时进行评价。在测试浓度为5ppm或更低时,活性化合物至少控制90%的猫栉首蚤。
方法B:Diabrotica undecimpunctata(南方玉米根叶甲)试验
施用前两天,在温暖条件下将玉米种子在水中浸泡,以引起快速发芽。施用前一天,将南方玉米根叶甲的卵转至置于塑料培养皿中的一半日本滤纸上。然后,将发芽的玉米种子置于滤纸旁的湿垫上。将3滴200微升测试化合物溶液小心地移至卵上。余量溶液置于玉米上,然后合上培养皿。将培养皿中经处理的卵保持在人工气候箱中6天。施用6天后,用双目显微镜评定化合物效果(与对照相比的死亡卵和/或幼虫百分比)。
在测试浓度为10ppm时,活性化合物至少控制90%的南方玉米根叶甲。
方法C:Nephotettix Cinciceps(黑尾叶蝉)筛选
将12株秆长为8cm的水稻植物叶片在所配制的测试化合物水溶液中浸5秒。待溶液流干后,将以该方式处理的水稻植物置于培养皿中,并且繁殖约20头黑尾叶蝉幼虫(3龄)。合上培养皿,然后放置在人工气候箱中(16小时日照/天,25℃,40-60%相对湿度)。放置6天后,测定黑尾叶蝉幼虫的死亡百分率。
在测试浓度为100ppm时,活性化合物引起至少98%的黑尾叶蝉幼虫死亡率。
方法D:筛选法,测试对Ctenocephalides felis(猫栉首蚤)的接触活性
将测试化合物溶液滴于滤纸上,进行干燥,将滤纸置于试管中并且用10头猫栉首蚤成虫侵染。将经处理的猫栉首蚤置于人工气候箱中(26℃,80%RH),在施用24和48小时后,评价与未处理的对照相比的效果百分率。
在测试浓度为1000ppm时,活性化合物接触控制至少70%的猫栉首蚤。
方法E:筛选法,测试对Rhipicephalus sanguineus(血红扇头蜱)的接触活性
将测试化合物溶液滴于滤纸上,进行干燥,将滤纸置于试管中并且用20-30头血红扇头蜱幼虫(1龄)侵染,并且用夹子密封试管。将经处理的血红扇头蜱置于人工气候箱中(25℃,90%RH),在施用24小时后,评价与未处理的对照相比的效果百分率。
在测试浓度为100ppm时,活性化合物接触控制至少70%的血红扇头蜱。
下列化合物号在一个或多个上述试验中有活性:
1-49,3-25,4-82,4-93,4-101,4-114,4-115,4-117,4-121,4-128,4-136,4-144,4-152,4-153,5-1,6-2,6-42,7-1,7-127。
Claims (15)
1. 式(Ia)或(Ib)化合物或其杀虫可接受的盐:
其中:
R1为未经取代或经一个或多个R15基团取代的芳基;或R19;
X和Y各自独立地为H或(C1-C6)-烷基;
W为C-卤素;
R2为卤素;
R3为(C1-C3)-卤烷基;
R4为H或(C1-C6)-烷基;
R5为H或为(C1-C6)-烷基;
R6和R13各自独立地为(C1-C6)-卤烷基;
R15为卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、S(O)pR13;
R19为未经取代或经一个或多个卤素取代的吡啶基;
m为1或2;
n和p各自独立地为0、1或2;
q为0或1;并且
在上述基团中的每个杂环基独立地为具有3至6个环原子,以及在环中具有选自N、O和S的1、2或3个杂原子的杂环基团。
2. 根据权利要求1的化合物或其盐,其特征在于:R1为未经取代或经一个或多个选自下组的基团取代的苯基:卤素、(C1-C6)-烷基、(C1-C6)-卤烷基、CN、S(O)pR13;并且R13为(C1-C3)-卤烷基。
3. 根据权利要求1或2所述的化合物或其盐,其特征在于:W为C-Cl。
4. 根据权利要求1或2所述的化合物或其盐,其特征在于:R2为Cl。
5. 根据权利要求1或2所述的化合物或其盐,其特征在于:R3为CF3。
6. 根据权利要求1或2所述的化合物或其盐,其特征在于:R4为H、(C1-C6)-烷基。
7. 根据权利要求1或2所述的化合物或其盐,其特征在于:R5为H、(C1-C6)-烷基。
8. 根据权利要求1或2所述的化合物或其盐,其特征在于:R6为CF3。
9. 根据权利要求1或2所述的化合物或其盐,其特征在于:m为1。
10. 根据权利要求1或2所述的化合物或其盐,其特征在于:R1为苯基;
X和Y各自独立地为H或甲基;
W为C-Cl;
R2为Cl;
R3和R6各自为CF3;
R4和R5各自独立地为H、甲基、乙基;并且
m为1。
11. 用于制备如权利要求1至10任一项所述的式(I)化合物或其盐的方法,该方法包括:
a)当式(I)为式(Ia),X为H,m和R1如权利要求1所定义,Y为不包括氢的如权利要求1所定义的基团,并且其它符号如权利要求1所定义时,将式(II)化合物与式(III)化合物反应:
(II)
其中,R2、R3、R4、R5、R6、W和n如权利要求1所定义,
Y-NH-O(CH2)mR1
(III)
其中R1如权利要求1所定义,并且Y为不包括氢的如权利要求1所定义的基团;或
b)当式(I)为式(Ia),X为H,m和R1如权利要求1所定义,Y为不包括氢的如权利要求1所定义的基团,并且其它符号如权利要求1所定义时,将式(IV)化合物与式(V)化合物反应:
其中各种符合如权利要求1所定义,
L-(CH2)mR1 (V)
其中R1和m如权利要求1所定义,并且L为离去基团;或
c)当式(I)为式(Ia),X为不包括氢的如权利要求1所定义的基团,并且其它符号如权利要求1所定义时,利用式(VI)化合物烷基化、酰化或磺酰化相应的其中X为H的式(Ia)化合物:
X-L1 (VI)
其中X为不包括氢的如权利要求1所定义的基团,L1为离去基团如卤素;或
d)当式(I)为式(Ia),X、Y和其它符号如权利要求1所定义时,通过式(VII)化合物与上述式(V)化合物反应:
其中各种符号如权利要求1所定义;或
e)当式(I)为式(Ib),X和Y均为H,并且m、R1和其它符号如权利要求1所定义时,通过权利要求1所述的式(II)化合物与式(VIII)化合物反应:
NH2-O(CH2)mR1
(VIII)
其中R1和m如权利要求1所定义;或
f)当式(I)为式(Ib),X为H,Y为不包括氢的如权利要求1所定义的基团,并且其它符号如权利要求1所定义时,通过利用式(IX)化合物烷基化、酰化或磺酰化相应的其中Y为H的式(Ib)化合物:
Y-L2 (IX)
其中Y为不包括氢的如权利要求1所定义的基团,L2为离去基团;或
g)当式(I)为式(Ib),X和Y为不包括氢的如权利要求1所定义的基团,并且其它符号如权利要求1所定义时,通过利用权利要求1所述的式(VI)化合物烷基化、酰化或磺酰化相应的其中X为H的式(Ib)化合物;或
h)当R1、R2、R3、R4、R5、R6、W、X、Y和m如权利要求1所定义,并且n为1或2时,通过氧化相应的其中n为0或1的化合物;和
i)视需要,将最终的式(I)化合物转化成其杀虫可接受的盐。
12.杀虫组合物,其包含与杀虫可接受的稀释剂或载体和/或表面活性剂相结合的如权利要求1至10任一项所述的式(I)化合物或其杀虫可接受的盐。
13. 权利要求1至10任一项所述的式(I)化合物或其盐,或权利要求12的组合物用于制备兽药的用途。
14. 权利要求1至10任一项所述的式(I)化合物或其盐,或权利要求12的组合物用于制备控制害虫的兽药的用途。
15. 在场所控制害虫的方法,其包括施用有效量的权利要求1至10任一项所述的式(I)化合物或其盐,或权利要求12的组合物。
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AR100936A1 (es) | 2014-06-24 | 2016-11-09 | Fmc Corp | Formulaciones de espumas y concentrados emulsionables |
CN109152360A (zh) | 2015-12-23 | 2019-01-04 | Fmc有限公司 | 犁沟内的种子原位处理 |
CN108148049B (zh) * | 2018-01-17 | 2020-03-10 | 河北大学 | 一种三嗪酮结构的5-吡唑酰胺类化合物制备方法与应用 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1210518A (zh) * | 1996-01-30 | 1999-03-10 | 武田药品工业株式会社 | 芳基吡唑杀虫剂 |
CN1316424A (zh) * | 1996-12-24 | 2001-10-10 | 罗纳-普朗克农业公司 | 1-芳基吡唑衍生物及其应用 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4631211A (en) | 1985-03-25 | 1986-12-23 | Scripps Clinic & Research Foundation | Means for sequential solid phase organic synthesis and methods using the same |
GB8713768D0 (en) * | 1987-06-12 | 1987-07-15 | May & Baker Ltd | Compositions of matter |
NO179282C (no) * | 1991-01-18 | 1996-09-11 | Rhone Poulenc Agrochimie | Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter |
AU685868B2 (en) * | 1993-11-09 | 1998-01-29 | Idemitsu Kosan Co. Ltd | Pyrazole derivatives and herbicide containing the same |
ZA9711534B (en) * | 1996-12-24 | 1998-06-24 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles. |
ZA981776B (en) * | 1997-03-10 | 1998-09-03 | Rhone Poulenc Agrochimie | Pesticidal 1-arylpyrazoles |
ZA200601794B (en) * | 2003-09-04 | 2007-04-25 | Bayer Cropscience Sa | Pesticidal 5-substituted-oxyalkylamino-1-arylpyrazole derivatives |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1210518A (zh) * | 1996-01-30 | 1999-03-10 | 武田药品工业株式会社 | 芳基吡唑杀虫剂 |
CN1316424A (zh) * | 1996-12-24 | 2001-10-10 | 罗纳-普朗克农业公司 | 1-芳基吡唑衍生物及其应用 |
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CN1720234A (zh) | 2006-01-11 |
EA009644B1 (ru) | 2008-02-28 |
CO5690508A2 (es) | 2006-10-31 |
US7514428B2 (en) | 2009-04-07 |
CA2508330A1 (en) | 2004-06-17 |
ES2417016T3 (es) | 2013-08-05 |
EP1599451B1 (en) | 2013-04-24 |
CA2508330C (en) | 2011-06-28 |
BRPI0316996B8 (pt) | 2022-08-23 |
JP4839463B2 (ja) | 2011-12-21 |
NZ540463A (en) | 2008-03-28 |
KR101146546B1 (ko) | 2012-07-03 |
WO2004050633A1 (en) | 2004-06-17 |
KR20050084101A (ko) | 2005-08-26 |
BR0316996B1 (pt) | 2013-12-10 |
AU2003289709A1 (en) | 2004-06-23 |
EP1599451A1 (en) | 2005-11-30 |
US20060241105A1 (en) | 2006-10-26 |
JP2006515288A (ja) | 2006-05-25 |
ZA200503744B (en) | 2006-11-29 |
BR0316996A (pt) | 2005-10-25 |
BRPI0316996B1 (zh) | 2013-12-10 |
EA200500931A1 (ru) | 2005-12-29 |
AU2003289709B2 (en) | 2008-09-04 |
BRPI0316996A2 (zh) | 2005-10-25 |
MXPA05005900A (es) | 2005-08-29 |
AR042256A1 (es) | 2005-06-15 |
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