CN101133022A - 用作杀真菌剂和杀虫剂的取代的2-吡咯烷酮衍生物 - Google Patents
用作杀真菌剂和杀虫剂的取代的2-吡咯烷酮衍生物 Download PDFInfo
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- CN101133022A CN101133022A CNA2005800302034A CN200580030203A CN101133022A CN 101133022 A CN101133022 A CN 101133022A CN A2005800302034 A CNA2005800302034 A CN A2005800302034A CN 200580030203 A CN200580030203 A CN 200580030203A CN 101133022 A CN101133022 A CN 101133022A
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- 238000010254 subcutaneous injection Methods 0.000 description 1
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- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
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- 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
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
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- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
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- BYGOPQKDHGXNCD-UHFFFAOYSA-N tripotassium;iron(3+);hexacyanide Chemical compound [K+].[K+].[K+].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] BYGOPQKDHGXNCD-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 239000004061 uncoupling agent Substances 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- SQOXTAJBVHQIOO-UHFFFAOYSA-L zinc;dicarbamothioate Chemical compound [Zn+2].NC([O-])=S.NC([O-])=S SQOXTAJBVHQIOO-UHFFFAOYSA-L 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/416—2,5-Pyrrolidine-diones 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 other 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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Abstract
式(I)化合物或其盐用于防治植物致病微生物或有害动物的用途,其中各符号具有说明书给出的含义。
Description
本发明涉及取代的杂环化合物、其制备方法及其用于防治植物致病真菌和有害昆虫的用途。
某些具有五元或六元Lactame环的化合物因其杀真菌活性而被知晓,例如霉腐利(Procymidone)、放线菌酮(Cycloheximide)和卡巴西霉素(Capsimycin)(参见“农药手册(The Pesticide Manual)”,第13版,C.D.S Tomlin(编辑),British Crop Protection Council,Farnham 2003)。
然而,由于现代农药必须满足各种各样的要求——例如有关作用水平、作用持续时间和作用谱、使用范围、毒性、与其他活性物质的结合、与制剂辅剂的结合或合成方面的要求,并且由于可能出现抗性,因此对这类物质的开发从未认为已终止,并且对新的、至少就某些方面而言优于已知化合物的化合物一直都有高的需求。
现已出人意料地发现某些取代的杂环化合物作为杀真菌剂和杀虫剂具有特别的活性。
这类化合物已在Yakugaku Zasshi,Pharmaceutical Society ofJapan 92(1972)1507和WO-A 04/071382中作为proteasom抑制剂进行了部分描述。但这类化合物对抗植物害虫和植物病原体的效用尚未有公开。
因此,本发明一方面提供式(I)化合物或其盐用于防治植物致病微生物或有害动物的用途
其中各符号具有下述含义:
R1相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、SO2NR2”、COOR”、COSR’、CSOR’、-O-COR”、-O-CSR’、-CO-R”或CONR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
n为0、1或2;
R2为氢、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、COOR”、CSOR”、COSR’、-CO-R”或者CONR2”;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C12)烯基、未取代或取代的(C3-C12)炔基、未取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、S(O)nR’、COOR’、CSOR’、COSR’、-CO-R’、CONR2”或者G;
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基、SO2zR’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”
或者
R5和R6一起形成键。
本发明另一方面提供一种防治植物致病微生物和有害动物的方法,该方法包括向植物致病微生物或动物害虫或其生境施用上述式(I)化合物。
本发明再一方面提供一种式(Ia)化合物或其盐,
其中各符号具有下述含义:
R1相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、COOR”、CSOR’、COSR’、-O-COR’、-O-CSR’、-CO-R”、CONR2”、SO2NR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
n为0、1或2;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
R2为未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基或未取代或取代的杂环基、COOR”、CSOR’、COSR’、-CO-R’或者CONR2”;
并且
R4为氢、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C6)环烯基、S(O)nR’、COOR’、CSOR’、COSR’、-CO-R’、CONR2”或者G;并且
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
条件是排除以下化合物:
本发明再一方面提供一种式(Ib)化合物或其盐,
其中各符号具有下述含义:
R1相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、COOR”、CSOR’、COSR’、-O-COR’、-O-CSR’、-CO-R”或CONR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
n为0、1或2;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
R2为未取代或取代的(C1-C5)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基或未取代或取代的杂环基、CSOR’、COSR’、-CO-R”或者CONR2”;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C6)环烯基、S(O)nR’、COOR’、CSOR’、-CO-R’、CON’R2”或者G;
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、SO2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
排除其中
R1=H,R2=CH3,R3=H,R4=H,C6H5,CH2-C6H5,C2H5,R5=H且R6=NH2,NHC6H5,NHCH2C6H5的化合物。
在其各种性质中,式(I)化合物主要依据取代基的性质,可以以旋光异构体的形式存在,或者以不同组成的异构体混合物的形式存在,所述混合物如果合适可通过常规方式分离。本发明提供了纯异构体和异构体混合物,及其制备和用途以及含有它们的组合物。然而,为简便起见,以下仅称式(I)化合物,但其含义既指纯化合物,并且如果合适也指不同比例的异构体的混合物。
本发明的盐优选为本发明化合物的农用化学可接受的盐。
化合物(I)的农用化学可接受的盐包括无机酸、羧酸和磺酸的酸加成盐,例如盐酸盐、氢溴酸盐、硫酸盐、磷酸盐、甲磺酸盐、乙磺酸盐、甲苯磺酸盐、苯磺酸盐、萘二磺酸盐、乙酸盐、丙酸盐、乳酸盐、酒石酸盐、苹果酸盐、柠檬酸盐、富马酸盐、马来酸盐和苯甲酸盐。
化合物(I)的农用化学可接受的盐还包括常规碱的盐,例如并优选碱金属的盐(例如钠盐和钾盐)、碱土金属的盐(例如钙盐和镁盐)以及衍生自氨或具有1至16个碳原子的有机胺的铵盐,所述有机胺示例性的并优选的有:乙胺、二乙胺、三乙胺、乙基二异丙胺、单乙醇胺、二乙醇胺、三乙醇胺、二环己胺、二甲氨基乙醇、普鲁卡因(procaine)、二苄胺、N-甲基吗啉、二氢化枞胺、精氨酸、赖氨酸、乙二胺和甲基哌啶。
在本说明书中,包括所附权利要求中,前述取代基具有如下含义:
卤素表示氟、氯、溴或碘。基团名前面的术语“卤代”表示该基团被部分或全部卤代,换言之,被F、Cl、Br或I以任何结合的方式所取代,优选被F或Cl所取代。
烷基及其部分(除非另外限定)可为直链或带有支链的。
词语“(C1-C6)烷基”应理解为具有1、2、3、4、5或6个碳原子的不带支链或带有支链的烃基,例如甲基、乙基、丙基、异丙基、1-丁基、2-丁基、2-甲基丙基或叔丁基。
烷基以及组合基团(composite group)中的烷基,除非另外限定,均优选具有1至4个碳原子。
(C1-C6)卤代烷基表示其中一个或多个氢原子被相同数量的相同或不同的卤素原子所取代的“(C1-C6)烷基”,例如一卤代烷基、全卤代烷基、CF3、CHF2、CH2F、CHFCH3、CH2CF3、CF2CF3、CF2CHF2、CHClCH2F、CCl3、CHCl2或CH2CH2Cl。
词语“(C1-C6)卤代亚烷基”应理解为表示其中一个或多个氢原子被相同数量的相同或不同的卤素原子所取代的在词语“(C1-C6)亚烷基”中提到的亚烷基。
“(C1-C6)烷氧基”表示其中碳链具有词语“(C1-C6)烷基”中给出含义的烷氧基。“卤代烷氧基”为例如,OCF3、OCHF2、OCH2F、OCF2CF3、OCH2CF3或OCH2CH2Cl。
“(C2-C6)烯基”表示不带支链或带有支链的非环状碳链,该碳链具有与所述范围相对应的碳原子数,并且含有至少一个可位于各不饱和基团任何位置的双键。因此“(C2-C6)烯基”表示,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”表示不带支链或带有支链的非环状碳链,该碳链具有与所述范围相对应的碳原子数,并且含有一个可位于各不饱和基团任何位置的三键。因此“(C2-C6)炔基”表示,例如,炔丙基、1-甲基-2-丙炔基、2-丁炔基或3-丁炔基。
环烷基优选在环中具有3至7个碳原子,并且可任选被卤素、(C1-C4)卤代烷基或(C1-C4)烷基所取代。
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为0或1并且v+w为1或2的“G”基团Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z表示,例如,如下基团:
SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe)。
“杂环基”优选表示含有一个或多个杂原子——优选选自N、O和S(O)m(m=0、1、2)的饱和的、不饱和的或3至10元芳环体系,其中至少一个碳原子在环中。
更优选的“杂环基”表示噻吩、呋喃、吡咯、噻唑、噁唑、咪唑、异噻唑、异噁唑、吡唑、1,3,4-噁二唑、1,3,4-噻二唑、1,3,4-三唑、1,2,4-噁二唑、1,2,4-噻二唑、1,2,4-三唑、1,2,3-三唑、1,2,3,4-四唑、苯并[b]噻吩、苯并[b]呋喃、吲哚、苯并[c]噻吩、1,3-苯并二恶茂、1,3-苯并二氧杂环己烷、苯并[c]呋喃、异吲哚、苯并噁唑、苯并噻唑、苯并咪唑、苯并异噁唑、苯并异噻唑、苯并吡唑、苯并噻二唑、苯并三唑、二苯并呋喃、二苯并噻吩、咔唑、吡啶、吡嗪、嘧啶、哒嗪,1,3,5-三嗪、1,2,4-三嗪、1,2,4,5-四嗪、喹啉、异喹啉、喹喔啉、喹唑啉、噌啉、1,8-萘啶、1,5-萘啶、1,6-萘啶、1,7-萘啶、2,3-二氮杂萘、吡啶并嘧啶、嘌呤、蝶啶、4H-喹嗪、吗啉、哌啶、哌嗪、吡咯啉、吡咯烷、噁唑啉、四氢呋喃、四氢吡喃、异噁唑烷、噁唑烷、噻唑啉、噻唑烷、环氧乙烷或氧杂环丁烷基。
特别优选的“杂环基”表示吡咯基、咪唑基、吡唑基、1,3,4-三唑基、1,2,4-噁二唑基、噁唑基、四唑基、吡啶基、吡嗪基、嘧啶基、1,3,5-三嗪基、吗啉基、哌啶基、噻吩基或噻唑基。
如果未在其各自的上下文中另外限定,则“取代的”表示,例如被一个或多个,优选一至三个,并且在卤素的情形下至多为最大数的选自下列的取代基所取代:卤素,R,OR,S(O)nR,SO2NR2,NR2,COOR,NHCOR,NHCOOR,G,CN,NO2,未取代的或被卤素和/或(C1-C4)烷基、(C6-C12)芳基和/或杂环基所取代的(C3-C6)环烷基,其中取代(C3-C6)环烷基的后两个取代基可为未取代的或被选自下列的一个或多个取代基所取代:卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、NO2和CN,
其中
n为0、1或2;
R为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、杂环基和(C6-C10)芳基,它们均为未取代的或被选自下列的一至五个取代基所取代:卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、NO2和CN;并且
G具有上面给出的含义。
“取代的”优选表示被一个或多个,优选一至三个,并且在卤素的情形下至多为最大数的选自下列的取代基所取代:F、Cl、Br、I、R、OR、S(O)nR、SO2NR2、NR2、COOR、NHCOR、NHCOOR、G、CN、NO2,
其中
R为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、杂环基和(C6-C10)芳基,其中后四个基团为未取代的或被选自下列的一至五个取代基所取代:卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、NO2和CN;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为0或1并且v+w为1或2;
n为0、1或2。
更优选地,“取代的”表示被一个或多个,优选一至三个,并且在卤素的情形下至多为最大数的选自下列的取代基所取代:F、Cl、Br、R、OR、S(O)nR、SO2NR2、NR2、COOR、NHCOR、NHCOOR、G、CN和NO2,
其中
R为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烯基、杂环基和(C6-C10)芳基,其中后四个基团为未取代的或被选自下列的一至四个取代基所取代:氟、氯、溴、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、NO2和CN;
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe);
n为0、1或2。
特别优选地,“取代的”表示被一至三个,并且在卤素的情形下至多为最大数的选自下列的取代基所取代:氟、氯、R、OR、NR2、G、NO2和CN,
其中
R为H、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C2-C4)卤代烯基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、杂环基和苯基,它们均为未取代的或被选自下列的一至三个取代基所取代:氟、氯、(C1-C4)烷基、三氟甲基、二氟甲基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、NO2和CN;并且
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe);
式(I)中的符号优选具有下述含义:
R1相同或不同,优选为氢、氯、溴、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、OR”、COOR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
R2优选为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基。
R3优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、COOR”、-CO-R”或者CONR2”。
R4优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C10)烯基、未取代或取代的(C3-C10)炔基、SO2R’、COOR’、-COR’、CONR2”或者G。
R5优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的苯基、未取代或取代的杂环基、SO2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G。
G优选为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2。
R6优选为OR”、SR”或NR2”
或者
R5和R6优选一起形成键。
R’相同或不同,优选为(C1-C10)烷基、(C2-C10)烯基、(C2-C10)炔基、(C3-C6)环烷基、(C3-C6)环烯基、苯基或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,优选为H或R’。
n 优选为0、1或2。
优选的为其中所有符号均具有优选含义并且“取代的”也具有优选含义的式(I)化合物。
更优选的式(I)化合物为式(II)化合物,
其中各符号具有下述含义:
R1相同或不同,为氢、氯、溴、未取代或取代的(C1-C10)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的苯基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、COOR”、OR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环;
R2为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、或者G;
R5为氢、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR’、CONR2”、未取代或取代的苯基、未取代或取代的杂环基、或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
或者
R5和R6一起形成键;
R7为氢、氟、氯、O-R”、SR”、NR”2、-O-COR’、-S-COR’、-O-CSR’、-O-SO2R’、-O-COOR’、-O-CSOR’、-O-CONR2”、NO2或CN;
R8为氢、未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
或者
R7和R8一起为=O或=S;
R9为氢、卤素、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R’或SR’;
或者
R8和R9一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环,
R’相同或不同,为(C1-C8)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代或取代的;
并且
R”相同或不同,为H或R”;
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe);
n为0、1或2。
优选的为其中“取代的”具有优选含义的式(II)化合物。更优选的为其中“取代的”具有更优选含义的式(II)化合物。
特别优选的为其中符号具有下述含义的式(II)化合物:
R1相同或不同,特别优选为氢,氯,溴,(C1-C8)烷基,(C2-C6)烯基,(C2-C8)炔基,苯基,其中后四者基团为未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代,未取代的或被氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2或CN所取代的杂环基,未取代的或被选自氟、氯、甲基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的(C3-C6)环烷基或(C3-C8)环烯基,或者两个R1取代基一起形成三至六元碳环。
R2特别优选为氢,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的甲基、乙基、丙基、异丙基、烯丙基、炔丙基、环丙基、环丁基、环戊基、环己基、苯基,或未取代的或被选自氟、氯、甲基、乙基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的杂环基。
R4特别优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、CONR2”或者G。
R5特别优选为氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C8)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR’、CONR2”
或者G。
R6特别优选为OR”、SR”或NR2”,
或者特别优选
R5和R6一起形成键。
R7特别优选为羟基、巯基、SCH3、氟、氯、溴、甲基、乙基、甲氧基、三氟甲氧基、乙氧基、-O-SO2R’、-O-COOR’、-O-CONR2”、CN、NR”或O-G。
R8特别优选为氢,未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的苯基,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的杂环基;
或者特别优选
R7和R8一起为=O或=S。
R9特别优选为氢、卤素、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、炔丙基、未取代或取代的(C6-C10)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基;
或者特别优选
R8和R9一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
G特别优选
为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
R’相同或不同,特别优选为(C1-C6)烷基、(C2-C4)烯基、(C2-C4)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,特别优选为H或R’。
特别优选的为其中所有符号和术语“取代的”具有特别优选含义的式(II)化合物。
还特别优选的是式(III)化合物,
其中,
R10代表氢或羟基,
R11代表环己基或环己-2-烯基,
R12代表氢或羟基,
还特别优选式(IIIa)化合物,
其中,
R10、R11和R12具有上述含义。
还特别优选的是下述式(I)化合物,
(1R,4R,5S)-1-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
(1R,4R,5S)-1-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-[1-羟基-己基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
以及
(1R,4R,5S)-1-[(1R)-2-环己烯-1-基甲基]-4-己基-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
在另一个特别优选的实施方案中,本发明涉及下式化合物
其中
R13代表氢或羟基,
R14代表其中环己基可被0至2个羟基所取代的环己基或环己-2-烯基,
R15代表氢或羟基,
并且
R16代表羟基或下式取代基
其中
R17代表氢或甲基,
并且
*代表与分子的连接位置。
还特别优选下式化合物
其中,
R13、R14、R15和R16具有上述含义。
还特别优选式(III)化合物,例如
(3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-3-羟基-4-[1-羟基-己基]-3-甲基-5-氧代-D-脯氨酸
N-乙酰基-S-({(2R,3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-3-羟基-3-甲基-5-氧代-2-吡咯烷基}羰基)半胱氨酸
以及
N-乙酰基-S-({(2R,3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-3-羟基-3-甲基-5-氧代-2-吡咯烷基}羰基)半胱氨酸甲酯
在式(Ia)化合物中,各符号和附标优选具有下述含义:
R1相同或不同,优选为氢、氯、溴、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、OR”、COOR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
R2优选为未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的苯基、或者未取代或取代的杂环基。
R3优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、COOR”、-CO-R’或者CONR2”。
R4优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C10)烯基、未取代或取代的(C3-C10)炔基、SO2R’、COOR’、-COR’、CONR2”或者G。
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2。
R’相同或不同,优选为(C1-C10)烷基、(C2-C10)烯基、(C2-C10)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,优选为H或R’。
优选地为其中所有符号具有优选含义并且“取代的”具有优选含义的式(Ia)化合物。
更优选的式(Ia)化合物为式(IIa)化合物,
其中各符号具有下述含义:
R1相同或不同,为氢、氯、溴、未取代或取代的(C1-C10)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的苯基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、COOR”OR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环;
R2为未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、或CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R7为氢、氟、氯、O-R”、SR”、NR”2、-O-COR’、-S-COR’、-O-CSR’、-O-SO2R’、-O-COOR’、-O-CSOR’、-O-CONR2”、NO2或CN;
R8为氢、未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
或者
R7和R8一起为=O或=S;
R9为氢、卤素、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R’或SR’;
或者
R8和R9一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
R’相同或不同,为(C1-C8)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代或取代的;
并且
R”相同或不同,为H或R”;并且
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
优选的为其中“取代的”具有优选含义的式(IIa)化合物。更优选的为其中“取代的”具有更优选含义的式(IIa)化合物。
特别优选的为其中各符号具有下述含义的式(II)化合物:
R1相同或不同,特别优选为氢,氯,溴,(C1-C8)烷基,(C2-C6)烯基,(C2-C8)炔基,苯基,其中后四者基团为未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代,未取代的或被氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2或CN所取代的杂环基,未取代的或被选自氟、氯、甲基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的(C3-C6)环烷基、(C3-C8)环烯基,或者两个R1取代基一起形成三至六元碳环。
R2特别优选为未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的甲基、乙基、丙基、异丙基、烯丙基、炔丙基、环丙基、环丁基、环戊基、环己基、苯基,未取代的或被选自氟、氯、甲基、乙基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的杂环基。
R4特别优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C10)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、-CONR2”或者G。
R7特别优选为羟基、巯基、SCH3、氟、氯、溴、甲基、乙基、甲氧基、三氟甲氧基、乙氧基、-O-SO2R’、-O-COOR’、-O-CONR2”、CN、NR”或O-G。
R8特别优选为氢,未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的苯基,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的杂环基;
或者特别优选
R7和R8一起为=O或=S。
R9特别优选为氢、卤素、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、炔丙基、未取代或取代的(C6-C10)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基;
或者特别优选
R8和R9一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
G特别优选
为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
R’相同或不同,特别优选为(C1-C6)烷基、(C2-C4)烯基、(C2-C4)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,特别优选为H或R’。
特别优选的为其中所有符号和术语“取代的”具有特别优选含义的式(IIa)化合物。
在式(Ib)化合物中,各符号和符标优选具有下述含义:
R1相同或不同,优选为氢、氯、溴、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、OR”、COOR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
R2优选为氢、未取代或取代的(C1-C5)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基。
R3优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、-CO-R”或者CONR2”。
R4优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C10)烯基、未取代或取代的(C3-C10)炔基、SO2R’、COOR’、-CO-R’、CONR2”或者G。
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8环烷基、未取代或取代的苯基、或者未取代或取代的杂环基、SO 2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G。
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为O或1并且v+w为1或2。
R6优选为OR”、SR”或NR2”。
R’相同或不同,优选为(C1-C10)烷基、(C2-C10)烯基、(C2-C10)炔基、(C3-C6)环烷基、苯基、或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,优选为H或R’。
优选的为其中所有符号具有优选含义并且“取代的”具有优选含义的式(Ib)化合物。
更优选的式(Ib)化合物为式(IIb)化合物,
其中各符号具有下述含义:
R1相同或不同,为氢、氯、溴、未取代或取代的(C1-C10)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的苯基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、COOR’、OR”或-CO-R’,或者两个R1取代基一起形成三至六元碳环;
R2为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、CONR2”或者G;
R5为氢、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR’、CONR2”、未取代或取代的苯基、未取代或取代的杂环基、或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
R7为氢、氟、氯、O-R”、SR”、-O-COR’、-S-COR’、-O-CSR’、-O-SO2R’、NR”2、-O-COOR’、-O-CSOR’、-O-CONR2”、NO2或CN;
R8为氢、未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
或者
R7和R8一起为=O或=S;
R9为氢、卤素、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R’或SR’,
条件是如果R7和R8一起为=O,R9不为OR’;
或者
R8和R9一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环,
R’相同或不同,为(C1-C8)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代或取代的;
并且
R”相同或不同,为H或R”;
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
n为0、1或2。
优选的为其中“取代的”具有优选含义的式(IIb)化合物。更优选的为其中“取代的”具有更优选含义的式(IIb)化合物。
特别优选的为其中各符号具有下述含义的式(IIb)化合物:
R1相同或不同,特别优选为氢,氯,溴,(C1-C8)烷基,(C2-C6)烯基,(C2-C8)炔基,苯基,其中后四者基团为未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代,未取代的或被氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2或CN所取代的杂环基,未取代的或被选自氟、氯、甲基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的(C3-C6)环烷基、(C3-C8)环烯基,或者两个R1取代基一起形成三至六元碳环。
R2特别优选为氢、未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的甲基、乙基、丙基、异丙基、烯丙基、炔丙基、环丙基、环丁基、环戊基、环己基、苯基,或者未取代的或被选自氟、氯、甲基、乙基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的杂环基。
R4特别优选为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR”、-CONR2”或者G。
R5特别优选为氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR”、CONR2”、或者G;
R6特别优选为OR”、SR”或NR2”,
R7特别优选为羟基、巯基、SCH3、氟、氯、溴、甲基、乙基、甲氧基、三氟甲氧基、乙氧基、-O-SO2R’、-O-COOR’、-O-CONR2”、CN、NR”或O-G。
R8特别优选为氢,未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的苯基,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的杂环基;
或者特别优选
R7和R8一起为=O或=S。
R9特别优选为氢、卤素、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、炔丙基、未取代或取代的(C6-C10)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基;
或者特别优选
R8和R9一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环。
G特别优选
为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
R’相同或不同,特别优选为(C1-C6)烷基、(C2-C4)烯基、(C2-C4)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的。
R”相同或不同,特别优选为H或R’。
特别优选的为其中所有符号和术语“取代的”具有特别优选含义的式(IIb)化合物。
本发明化合物由本身已从文献中知晓的方法来制备,如有机合成方面的权威著作所述,例如Houben.-Weyl,Methoden der OrganischenChemie[有机化学方法],Georg-Thieme-Verlag,Stuttgart中所述。
制备在已知的并且适用于上述反应的反应条件下进行。也可使用其他本身已知的、但未在本申请中详细说明的变化方案。
如果需要,原料可以以不从反应混合物中分离但立即进一步反应生成式(I)化合物的方式原位(in situ)形成。
具体而言,式(I)化合物可按照以下方法A至D进行制备:
方法A
按照文献中已知的、已完善制定的方法,在对自由胺(free amine)进行保护后,将甘氨酸或其甲酯转化为衍生氨基酸(例如,D.Enders,Helv.Chim Acta 85(2002)3657-3677)。R3通过以下方式引入。
受保护的氨基酸用含有R1和R2的、取代的β酮酸或其酯进行酰化。酰化作用使用二环己基碳二亚胺(DCC)、1-乙基-3-(3-二甲基-氨基丙基)碳二亚胺(EDC)或4-二甲基氨基吡啶(DMAP)进行。
该路线的关键步骤是内酯化作用。它以Romo等(G.S,Cortez,R.L.Tennyson,D.Romo J.Am.Chem.Soc.2001,123,7945)所述的亲核催化的羟醛内酯化(方法A)的方式进行,或以先进行标准碱催化的羟醛反应(方法B)并随后进行内酯化的方式(E.J.Corey等,Angew.Chem.1998,110,1784)进行。并且,可通过使用乙烯酮醛[2+2]-环加成作用(方法C,C.Zhu,X.shen,S.G.Nelson J.Am.Chem.SoC.2004,126,5352)获得内酯。路易斯酸催化的羟醛反应并随后进行内酯化是另一种可能的方法(方法D)。使用酮的催化羟醛反应的方法据报道为非立体控制(non-stereocontrolled)的反应(例如Kobayashi,S.等,Chem.Lett.1988,1491;Chen,J.等,J.Org.Chem.1988,63,9739)和对映立构选择性羟醛反应(Denmark,S.E.;Fan,Y.J.Am.Chem.Soc.2002,124,4233;Oisaki,K等,J.Am.Chem.Soc.2003,125,5644)。
式(Ia)化合物依照已知的文献方法合成。使氮去保护并且如果需要,用R4衍生化。
式(I)化合物依照已知的文献方法合成。首先,按照文献中已知的方法断开内酯环。在分子中引入R6。
使自由羟基(free hydroxy)衍生化以引入R5后,使氮去保护并且如果需要,用R4衍生化。
方法B
式(II)化合物按照文献方法(F.Souci,L.Grenier,M.L.Behnke,A.T.Destree,T.A.McCormack,J.Adams,L.Plamondon,J.Am.Chem.Soc.1999,121,9967)通过下述路线图所示的多步合成制备。
可实施该路线将所有产生立构的中心(stereogenic center)以所需构型引入。
方法C
按照文献方法[1],将丙二酸单苄酯转化为酰氯并随后用N-(对-甲氧基苄基)甘氨酸乙酯处理。
R1=H,R4=pmb
可能的变化方案(未公开):R1=芳基、烷基;R4=芳基、烷基
由氟化四丁铵引起环化反应,使用烷基碘、苄基碘或烯丙基碘进行烷基化(引入R1)[1]。
使用THF中的LHMDS(lithiumhexamethyldisilazid)和DMPU进行去质子化,使用氰基甲酸甲酯进行羧化[1]。
类似[2],可使用NaBH(OAc)3(R5=R2=R)进行酮还原。通过加入适宜的有机金属试剂(例如,格氏试剂)可引入取代基R2(例如,烷基、烯丙基、芳基)。
保护氧后(R5=甲硅烷基、苄基),可加入烷基和醛。
(R3=烷基、烯丙基、苄基或者R7=烷基、烯丙基、苄基、芳基,R8=OH)
根据[1],烯丙基溴易于反应。
参见4
8-11
类似[2]:加入甲醛(8),酮还原(参见(4)),将伯羟基保护为新戊酯,将仲羟基保护为TBS醚,将新戊酯去保护(9),Dess-Martin氧化(10),加入格氏试剂[2]或锌金属有机化合物[3](11)
可能的转化有
——脱羧作用(R1不再连有CO2Bn):Pd催化的氢解作用产生脱苄基作用并引起脱羧作用[1]
——如果R4为PMB,使用Cer(ammonium)nitrat(CAN)使氮去保护(R4=H)[2]
——酯交换(R6=O-烷基、O-烯丙基、O-苄基)
——皂化作用(R6=OH)
——形成硫代酸酯(R6=S-烷基)
——形成酰胺(R6=NH-烷基/芳基、N-烷基-芳基、N-二烷基)
13
使用BOP-Cl的内酯化作用描述于[2]中。
文献:
[1]P.C.Bulman Page等,SYNLETT 2003,1025。
[2]E.J.Corey等,Angew.Chem.1998,110,1784。
[3]L.R.Reddy,P.Saravanan,E.J.Corey,J.Am.Chem.Soc.,ASAP
方法D
R2=H的式(I)化合物可按照文献方法(E.J.Corey,W.Li,T.Nagamitsu,Angew.Chem.IE1998,37,1676-1679)以对映异构纯的、取代的丙二酸酯为原料通过方法路线图中所示的多步合成制备。该合成路线对于R1具有高度的灵活性并且可以以完全立体控制的方式进行。关键中间体Z使得R3可有多种变化。
方法E
该方法基于文献(Corey等,J.Am.Chem.Soc.2004,126,6230-6231)中所述的方法。
按照文献方法,用4-甲氧基苯酰氯使丝氨酸甲酯的衍生物N-酰化以形成酰胺,将得到的酰胺通过与对甲苯磺酸一起加热环化成噁唑啉。
用二异丙基氨基化锂使噁唑啉去质子化,并用氯甲基苄基醚使得到的烯醇化物烷基化,得到所需的异构体。
用氰基硼氢钠进行还原得到PMB-胺(PMB=4-甲氧基苄基),它可通过与Me3SiCl和Et3N反应转化为N-烯丙酰-N-PMB衍生物以形成三甲基甲硅烷基醚,然后用烯丙酰氯酰化并进行酸性处理。
Dess-Martin过碘烷(periodinane)氧化得到酮酰胺酯。
酮酰胺酯可使用奎宁环作为催化碱通过Baylis-Hillman羟醛内反应环化成γ-内酰胺。环化反应的产物可用溴甲基二甲基甲硅烷基氯甲硅烷化并通过柱色谱法分离。
γ-内酰胺中心可通过氢化三正丁基锡介导(mediate)的自由基链环化作用完全转化为顺-稠合双环γ-内酰胺。
在钯/活性炭上用氢气使二苄醚断开,并进行Dess-Martin过碘烷氧化作用得到醛。
通过加入适宜的有机金属试剂,例如格氏试剂,或者通过进行Wittig反应然后使生成的烯烃水合可将该醛转化为取代基R3。
双环的Tamao-Fleming氧化作用得到对应的PMB保护的二醇酯。
该二醇酯可能的转化有
——将伯羟基氧化为醛,然后进行Wittig反应,并使生成的烯烃还原以改变R1取代基
——使仲羟基(例如R5=烷基、烯丙基、苄基、酰基等)衍生化(例如烷基化、酰化等)
——酯交换(例如R6=O-烷基、O-烯丙基、O-苄基)
——皂化作用(例如R6=OH)
——形成硫代酸酯(例如R6=S-烷基)
——形成酰胺(例如R6=NH-烷基/芳基、N-烷基-芳基、N-二烷基)
12
在Ce(IV)引起PMB基团的氧化断裂后,如果需要,可通过使用标准方法使酰胺N-烷基化(R4=烷基、苄基等)。
通过使用双-(2-氧代-3-噁唑烷基)次磷酰氯(BOPCl)使β-醇酸(R4=R5=R6=H)内酯化为式(Ia)化合物。如果需要,在该阶段也可使酰胺N-烷基化(R4=烷基、烯丙基、苄基等)。
方法F
在保护-烷基化-去保护作用工序中,得到取代的二乙基氨基丙二酸酯。可能的变化方案:R3=烷基、烯丙基、苄基取代的烷基
在温和的条件下进行N-酰化作用。可能的变化方案:R1=无限制
碱引起的环化作用生成特特拉姆酸(tetramic acid)。
下一步通过还原或加入适当的有机金属试剂(例如格氏试剂)进行。
可能的变化方案:R2=H、烷基、苄基、芳基
采用BOP-Cl进行内酯化。
可能的转化有:
——引入R4=烷基、苄基、酰基、磺酰基
——引入R5=烷基、苄基、酰基、磺酰基
——酯交换(R6=O-烷基、O-烯丙基、O-苄基)
——皂化作用(R6=OH)
——形成硫代酸酯(R6=S-烷基)
或其结合。
此外,式(II)化合物可通过如下方法制备:
[A]一种合成通式(IIIc)化合物的方法,
其中
R10和R12具有上述含义,
该方法的特征在于所述化合物通过发酵并从链霉菌(Streptomyces)属的放线菌中分离制得;
或者
[B]一种合成通式(IIId)化合物的方法,
其中
R10和R13具有上述含义,
该方法的特征在于所述化合物通过使(IIIc)化合物中的双键氢化制得;
或者
[C]一种合成通式(IIIe)化合物的方法,
其中
R10和R13具有上述含义,
羟基连接到碳原子1或2上,
该方法的特征在于所述化合物通过使(IIIc)化合物中的双键水合制得;
或者
[D]一种合成通式(IIIf)化合物的方法,
其中
R10和R12具有上述含义,
该方法的特征在于所述化合物通过使(IIIc)化合物中的双键氧化制得;
或者
[E]一种合成通式(IIIb)化合物的方法,
其中
R13、R14、R15和R16具有上述含义,
该方法的特征在于所述化合物通过发酵并从链霉菌(Streptomyce.s)属的放线菌中分离制得。
方法[A]和[E]按照实验部分中所述的进行。
方法[B]中的氢化作用可在催化剂和氢的存在下,在适当溶剂中,在0℃至+100℃的温度范围内,在常压下或升高到至多3巴的压力下进行,所述催化剂例如钯/活性炭。
适合的溶剂为:即醚,例如乙醚、甲基叔丁基醚、二噁烷或四氢呋喃;醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇或叔丁醇;优选甲醇、乙醇、异丙醇或四氢呋喃。
方法[C]中的水合作用可使用例如四氢呋喃中的乙硼烷(B2H6)随后使用过氧化氢进行氧化处理通过硼氢化作用进行。或者,可生成环氧化物并通过还原方法使其打开。所有方法均在适当溶剂中,在-78℃至+25℃的温度范围内,在常压下或升高到至多3巴的压力下进行,
适合的溶剂为:即四氢呋喃、乙醚、甲基叔丁基醚以及所述溶剂。
方法[D]中的氧化作用可使用高锰酸钾(KMnO4)或四氧化锇(OsO4)通过手性或非手性的二羟基化方法进行。在四氧化锇情形中,当使用叔胺N-氧化物,例如N-甲基-吗啉-N-氧化物或其他氧化剂,例如铁氰化钾(K3FeCN6)时,催化量可为充足的。所有方法均在适当溶剂中,在0℃至+100℃的温度范围内,在常压下或升高到至多3巴的压力下进行。
适当溶剂为加有适量水的醇,例如乙醇或叔丁醇。
本发明化合物表现出强的杀微生物活性。因此,它们可用于在农业和园艺中对抗不良微生物,例如植物致病真菌和细菌。所述化合物适于直接防治不良微生物以及使植物对不良植物病原体的侵袭产生抵抗力。
本申请中产生抵抗力的物质应理解为能刺激植物——例如处理过的植物的防御系统,使其在随后接种有不良微生物时表现出对这些微生物的显著抵抗力的物质。
本申请中不良微生物应理解为植物致病真菌和细菌。因此可采用本发明物质使植物在处理后的某段时间内对所述有害微生物的侵袭产生抵抗力。用活性化合物处理植物后产生抵抗力的时间通常为1至10天,优选1至7天。
通常,本发明化合物可用作对抗植物致病真菌的杀真菌剂,并且还可用作对抗细菌的杀细菌剂,所述真菌例如根肿菌(Plasmodiophoromycetes)、卵菌(Oomycetes)、壶菌(Chytridiomycetes)、接合菌(Zygomycetes)、子囊菌(Ascomycetes)、担子菌(Basidiomycetes)和半知菌(Deuteromycetes),所述细菌例如假单胞菌(Pseudomonadaceae)、根瘤菌(Rhizobiaceae)、肠杆菌(Enterobacteriaceae)、棒状杆菌(Corynebacteriaceae)和链霉菌(Streptomycetaceae)、proteobacteriae和革兰氏阳性种。
一些归入上述属名、可导致真菌性病害的病原体可作为非限制性实例提出:
欧文氏(Erwinia)属种,例如解淀粉欧文氏菌(Erwiniaamylovora);
腐霉(Pythium)属种,例如终极腐霉(Pythium ultimum);
疫霉(Phytophthora)属种,例如致病疫霉(Phytophthorainfestans);
假霜霉(Pseudoperonospora)属种,例如草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);
轴霜霉(Plasmopara)属种,例如葡萄生轴霜霉(Plasmoparaviticola);
盘霜霉(Bremia)属种,例如莴苣盘霜霉(Bremia lactucae);
霜霉(Peronospora)属种,例如豌豆霜霉(Peronospora pisi)或十字花科霜霉(P.brassicae);
白粉菌(Erysiphe)属种,例如禾谷白粉菌(Erysiphe graminis);
单囊壳属(Sphaerotheca)属种,例如凤仙花单囊壳(Sphaerothecafuliginea);
叉丝单囊壳属(Podosphaera)属种,例如白叉丝单囊壳(Podosphaera leucotricha);
黑星菌属(Venturia)属种,例如苹果黑星病菌(Venturiainaequalis);
核腔菌属(Pyrenophora)属种,例如圆核腔菌(Pyrenophorateres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,Syn:Helminthosporium);
旋孢腔菌属(Cochliobolus)属种,例如禾旋孢腔菌(Cochliobolussativus)(分生孢子形式:Drechslera,Syn:Helminthosporium);
单胞锈菌属(Uromyces)属种,例如疣顶单胞锈菌(Uromycesappendiculatus);
柄锈菌(Puccinia)属种,例如隐匿柄锈菌(Puccinia recondita);
核盘菌属(Sclerotinia)属种,例如油菜菌核病菌(Sclerotiniasclerotiorum);
腥黑粉菌属(Tilletia)属种,例如小麦网腥黑粉菌(Tilletiacaries);
黑粉菌(Ustilago)属种,例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属(Pellicularia)属种,例如佐佐木薄膜革菌(Pellicularia sasakii);
梨孢(Pyricularia)属种,例如稻梨孢(Pyricularia oryzae);
镰孢属(Fusarium)属种,例如黄色镰孢(Fusarium culmorum);
葡萄孢属(Botrytis)属种,例如灰葡萄孢(Botrytis cinerea);
壳针孢属(Septoria)属种,例如Leptosphaeria nodorum;
尾孢属(Cercospora)属种,例如变灰尾孢(Cercosporacanescens);
链格孢属(Alternaria)属种,例如芸薹链格孢(Alternariabrassicae);
假小尾孢属(Pseudocercosporella)属种,例如小麦基腐病菌(Pseudocercosporella herpotrichoides);和
层锈菌属(Phakopsora)属种,例如,大豆锈病(Phakopsorapachyrhizi)和层锈层假尾孢菌(Phakopsora meibomiae)。
本发明的化合物特别适用于使植物对下述植物病原体的感染产生抵抗力,所述病原体例如稻梨孢、致病疫霉(Phythophthora infestans)等。
本发明活性化合物在防治植物病害所需浓度下具有良好的植物耐受性,这使得可以对植物的地上部分、离体繁殖株(propagationstock)和种子以及土壤进行处理。
本发明的化合物对温血动物具有低毒性,并因此可以安全地使用。
本发明的活性化合物可转化为常规制剂,例如溶液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、片剂、气雾剂、用活性化合物浸渍过的天然和合成材料、聚合物中的微胶囊剂、用于种子的包衣组合物、与燃烧装置——例如熏蒸盒、熏蒸罐和熏蒸线圈一起使用的制剂、以及ULV冷雾(cold mist)与暖雾(warm mist)制剂。
这些制剂可以以已知方式制备,例如将活性化合物与填充剂混合,即与液体或液化气或固体稀释剂或载体混合,同时可选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。如果使用的填充剂为水,还可使用例如有机溶剂作为助溶剂。
适合的液体溶剂稀释剂或载体主要有:芳烃,例如二甲苯、甲苯或烷基萘;氯化芳烃或氯化脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡(如矿物油馏分);醇,例如丁醇或乙二醇及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;或强极性溶剂,例如二甲基甲酰胺和二甲基亚砜,以及水。
液化气稀释剂或载体的含义应被理解为常温及常压下为气态的液体,例如气溶胶喷雾剂,例如卤代烃,以及丁烷、丙烷、氮气及二氧化碳。
固体载体可使用:粉碎的天然矿物,例如高岭土、粘土、滑石粉、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成矿物,例如高分散硅酸、氧化铝及硅酸盐。适用于颗粒剂的固体载体可使用:粉碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石及白云石,以及合成的无机及有机粉颗粒,以及有机物颗粒,例如锯木屑、椰壳、玉米穗芯及烟草茎。
适合的乳化剂和/或发泡剂可使用:非离子及阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚例如烷基芳基聚乙二醇醚,烷基磺酸酯、烷基硫酸酯、芳基磺酸酯以及清蛋白水解产物。
分散剂包括:例如木素亚硫酸盐废液及甲基纤维素。
所述制剂中可使用粘合剂,例如羧甲基纤维素,以及粉末、颗粒或胶乳形式的天然及合成聚合物,例如阿拉伯树胶、聚乙烯醇及聚乙酸乙烯酯。
可使用着色剂,例如无机颜料,例如氧化铁、氧化钛及普鲁士蓝,以及有机染料,例如茜素染料、偶氮染料或金属酞菁染料,以及微量营养物,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐及锌盐。
所述制剂一般包括0.1至95重量%的活性化合物,优选0.5至90重量%。
本发明的活性化合物可以制剂形式存在或以与其它已知的活性化合物的混合物的多种使用形式存在,所述活性化合物例如杀真菌剂、杀细菌剂、杀昆虫剂、杀螨剂、杀线虫剂、除草剂、驱鸟剂、生长素(growth factor)、植物营养素以及土壤结构改良剂。
在许多情况下,获得协同效应,即混合物的活性高于单组分的活性。
混合物中共存组分(co-componet)的实例有如下化合物:
杀真菌剂:
1.核酸合成的抑制
1.1苯霜灵(benalaxyl)、benalaxyl-M、乙嘧酚磺酸酯(bupirimate)、chiralaxyl、clozylacon、甲菌定(dimethirimol)、乙菌定(ethirimol)、呋氨丙灵(furalaxyl)、土菌消(hymexazol)、精甲霜灵(metalaxyl-M)、甲呋酰胺(ofurace)、噁霜灵(oxadixyl)、喹菌酮(oxolinicacid)
2.有丝分裂与细胞分裂的抑制
2.1苯菌灵(benomyl)、多菌灵(carbendazim)、乙霉威(diethofencarb)、麦穗宁(fuberidazole)、戊菌隆(pencycuron)、涕必灵(thiabendazole)、甲基托布津(thiophanate-methyl)、氯苯恶唑胺(zoxamide)
3.呼吸作用的抑制
3.1CI:氟嘧菌胺(diflumetorim)
3.2CII:啶酰菌胺(boscalid)、萎锈灵(carboxin)、甲呋酌苯胺(fenfuram)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、丙氧灭锈胺(mepronil)、氧化萎锈灵(oxycarboxine)、吡噻菌胺(penthiopyrad)、溴氟唑菌(thifluzamide)
3.3CIII:腈嘧菌酯(azoxystrobin)、氰霜唑(cyazofamid)、醚菌胺(dimoxystrobin)、enestrobin、噁唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、吡唑醚菌酯(pyraclostrobin)、啶氧菌酯(picoxystrobin)、肟菌酯(trifloxystrobin),
3.4解偶联剂:敌螨普(dinocap)、氟啶胺(fluazinam)
3.5ATP产生的抑制:薯瘟锡(fentin acetate)、三苯锡氯(fentinchloride)、毒菌锡(fentin hydroxide)、硅噻菌胺(silthiofam)
4.AA与蛋白质生物合成作用的抑制
4.1氨丙膦酸钾(andoprim)、灭瘟素(blasticidin-S)、嘧菌环胺(cyprodinil)、春雷霉素(kasugamycin)、盐酸春雷霉素水合物(kasugamycin hydrochlorid hydrate)、嘧菌胺(mepanipyrim)、二甲嘧菌胺(pyrimethanil)
5.信号转导作用的抑制
5.1拌种咯(fenpiclonil)、氟噁菌(fludioxonil)、喹氧灵(quinoxyfen)
6.脂质与膜合成的抑制
6.1乙菌利(chlozolinate)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin)
6.2定菌磷(pyrazophos)、克瘟散(edifenphos)、异稻瘟净(iprobenfos(IBP))、稻瘟灵(isoprothiolane)
6.3甲基立枯磷(tolclofos-methyl)、联苯(biphenly)
6.4iodocarb、百维灵(propamocarb)、盐酸百维灵(propamocarbhydrochloride)
7.麦角固醇生物合成的抑制
7.1环酰菌胺(fenhexamid)
7.2戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、苄氯三唑醇(diclobutrazole)、噁醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇-M(diniconazole-M)、氧唑菌(epoxiconazole)、乙环唑(etaconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、呋菌唑(furconazole)、furconazole-cis、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazol)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、伏立康唑(voriconazole)、烯菌灵(imazalil)、硫酸烯菌灵(imazalilsulfate)、恶咪唑(oxpoconazole)、异嘧菌醇(fenarimol)、呋嘧醇(flurprimidol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、稻瘟酯(pefurazoate)、丙氯灵(prochloraz)、氟菌唑(triflumizole)、烯霜苄唑(viniconazole),
7.3 aldimorph、十二环吗啉(dodemorph)、吗菌灵(dodemorphacetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph)、苯锈啶(fenpropidin)、螺噁茂胺(spiroxamine)
7.4萘替芬(naftifine)、稗草畏(pyributicarb)、特比萘芬(terbinafine),
8.细胞壁合成的抑制
8.1苯噻菌胺(benthiavalicarb)、双丙氨膦(bialaphos)、烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、缬霉威(iprovalicarb)、多抗霉素(polyoxins)、多氧霉素(polyoxorim)、有效霉素A(validamycin A)
9.黑素生物合成的抑制
9.1氯环丙酰胺(carpropamid)、双氯氰菌胺(diclocymet)、稻瘟酰胺(fenoxanil)、phtalide、咯喹酮(pyroquilon)、三环唑(tricyclazole),
10.宿主防御诱导物
噻二唑素(acibenzolar-S-methyl)、烯丙苯噻唑(probenazole)、噻酰菌胺(tiadinil)
11.多位点(multisite)
11.1敌菌丹(captafol),克菌丹(captan),百菌清(chlorothalonil),铜制剂例如:氢氧化铜、环烷酸铜、氯氧化铜(copper oxychloride)、硫酸铜、氧化铜、喹啉铜(oxine-copper)和波尔多液混合物(Bordeaux mixture),苯氟磺胺(dichlofluanid)、二氰蒽醌(dithianon)、多果定(dodine)、多果定游离碱(dodine freebase)、福美铁(ferbam)、fluorofolpet、灭菌丹(folpet)、双胍盐(guazatine)、双胍辛乙酸盐(guazatine acetate)、双胍辛胺(iminoctadine)、双八胍盐(iminoctadine albesilate)、双胍辛醋酸盐(iminoctadine triacetate)、代森锰铜(mancopper)、代森锰锌(mancozeb)、代森锰(maneb)、代森联(metiram、metriamzinc)、丙森锌(propineb)、硫和硫制剂包括多硫化钙、福美双(thiram)、甲苯磺菌胺(tolylfluanid)、代森锌(zineb)、福美锌(ziram),
12.未知
12.1
amibromdole、苯噻硫氰(benthiazole)、bethoxazin、卡巴西霉素(capsimycin)、香芹酮(carvone)、灭螨猛(chinomethionat)、氯化苦(chloropicrin)、硫杂灵(cufraneb)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、双乙氧咪唑威(debacarb)、哒菌清(diclomezine)、双氯酚(dichlorophen)、氯硝胺(dicloran)、双苯唑快(difenzoquat、difenzoquatmethylsuphate)、二苯胺(diphenylamine)、韩乐宁(ethaboxam)、嘧菌腙(ferimzone)、氟联苯菌(flumetover)、磺菌胺(flusulfamide)、藻菌磷(fosetyl-aluminium)、藻菌磷钙(fosetyl-calcium)、藻菌磷钠(fosetyl-sodium)、氟吡菌胺(fluopicolide)、氟氯菌核利(fluoromide)、六氯苯(hexachlorobenzene)、8-羟基喹啉(8-hydroxyquinoline sulfate)、人间霉素(irumamycin)、磺菌威(methasulphocarb)、苯菌酮(metrafenone)、甲基异硫氰酸盐(methylisothiocyanate)、米多霉素(mildiomycin)、多马霉素(natamycin)、福美镍(nickel dimethyldithiocarbamate)、异丙消(nitrothal-isopropyl)、异噻菌酮(octhilinone)、oxamocarb、oxyfenthiin、五氯苯酚及其盐、2-苯基苯酚及其盐、磷酸及其盐、粉病灵(piperalin)、propanosine-sodium、丙氧喹啉(proquinazid)、硝吡咯菌素(pyrrolnitrine)、五氯硝基苯(quintozene)、叶枯酞(tecloftalam)、四氯硝基苯(tecnazene)、唑菌嗪(triazoxide)、水杨菌胺(trichlamide)、氰菌胺(zarilamid)、以及2,3,5,6-四氯-4-(甲磺酰基)吡啶、N-(4-氯-2-硝基苯基)-N-乙基-4-甲基-苯磺酰胺、2-氨基-4-甲基-N-苯基-5-噻唑甲酰胺、2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺、3-[5-(4-氯苯基)-2,3-二甲基异噁唑烷-3-基]吡啶、顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、3,4,5-三氯-2,6-吡啶二腈、2-[[[环丙基[(4-甲氧基苯基)亚氨基]甲基]硫代]甲基]-α-(甲氧基-亚甲基)-苯乙酸甲酯、4-氯-α-丙炔氧基-N-[2-[3-甲氧基-4-(2-丙炔氧基)苯基]乙基]苯乙酰胺、(2S)-N-[2-[4-[[3-(4-氯苯基)-2-丙炔基]氧基]-3-甲氧基苯基]乙基]-3-甲基-2-[(甲磺酰基)氨基]丁酰胺、5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑[1,5-a]嘧啶、5-氯-6-(2,4,6-三氟苯基)-N-[(1R)-1,2,2-三甲基丙基][1,2,4]三唑并[1,5-a]嘧啶-7-胺、5-氯-N-[(1R)-1,2-二甲基丙基]-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶-7-胺、N-[1-(5-溴-3-氯代吡啶-2-基)乙基]-2,4-二氯烟酰胺、N-(5-溴-3-氯代吡啶-2-基)甲基-2,4-二氯烟酰胺、2-丁氧基-6-碘-3-丙基-benzopyranon-4-酮、N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基-乙酰胺、N-(3-乙基-3,5,5-三甲基-环己基)-3-甲酰氨基-2-羟基-苯酰胺、2-[[[[1-[3-(1-氟-2-苯基乙基)氧基]苯基]亚乙基]氨基]氧基]甲基]-α-(甲氧基亚氨基)-N-甲基-αE-苯乙酰胺、N-{2-[3-氯-5-(三氟甲基)吡啶-2-基]乙基}-2-(三氟甲基)苯酰胺、N-(3’,4’-二氯-5-氟代联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基-1H-咪唑-1-羧酸、O-[1-[(4-甲氧基苯氧基)甲基]-2,2-二甲基丙基]-1H-咪唑-1-羧酸、2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟代嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺
杀细菌剂:
溴硝丙二醇(bronopol)、双氯酚、三氯甲基吡啶(nitrapyrin)、福美镍(nickel-dimethyldithiocarbamate)、春雷霉素、异噻菌酮(octhilinone)、羧酸呋喃(furancarboxylic acid)、土霉素(oxytetracyclin)、噻菌灵(probenaazole)、链霉素(streptomycin)、叶枯酞(tecloftalam)、硫酸铜及其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
1.乙酰胆碱酯酶(AChE)抑制剂
1.1氨基甲酸酯类,
例如:
棉铃威(alanycarb)、涕灭成(aldicarb)、砜灭威(aldoxycarb)、除害威(allyxycarb)、灭害威(aminocarb)、甲基吡恶磷(azamethiphos)、
噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、必克虱(bufenoarb)、畜虫威(butacarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、
西维因(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、除线威(chloethocarb)、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、
敌蝇威(dimetilan)、
苯虫威(ethiofencarb)、
丁苯威(fenobucarb)、苯硫威(fenothiocarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、
威百亩(metam-sodium)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭成(metolcarb)、
甲氨叉威(oxamyl)、
抗蚜威(pirimicarb)、猛杀威(promecarb)、残杀威(propoxur)、硫双灭多威(thiodicarb)、特氨叉威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、
XMC、灭杀威(xylylcarb)
1.2有机磷酸酯类,
例如:
高灭磷(acephate)、唑啶磷(azamethiphos)、谷硫磷(azinphos-methyl)、乙基谷硫磷(azinphos-ethyl)、
乙基溴硫磷(bromophos-ethyl)、溴苯烯磷(bromfenvinfos(-methyl))、特嘧硫磷(butathiofos)、
硫线磷(cadusafos)、三硫磷(carbophenothion)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chloromephos)、甲基毒死蜱(chloropyrifos-methyl)、乙基毒死蜱、蝇毒磷(coumaphos)、苯腈磷(cyanofenphos)、杀螟腈(cyanophos)、毒虫畏(chlorofenvinphos)、
甲基-○五九(demeton-S-methyl)、磺吸磷(demeton-S-methylsulphon)、氯亚磷(dialifos)、二嗪农(diazinon)、除线磷(dichlofenthion)、敌敌畏(dichlorovos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、蔬果磷(dioxabenzofos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氧嘧啶磷(etrimfos)、
氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、丰索磷(fensulfothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazofos)、地虫磷(fonofos)、安果(formothion)、丁苯硫磷(fosmethilan)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、
碘硫磷(iodofenphos)、异稻瘟净(iprobenfos)、氟唑磷(isazofos)、丙胺磷(isofenphos)、邻-水杨酸异丙酯、异噁唑啉(isoxathion)、
马拉松(malathion)、灭蚜磷(mecarbam)、虫螨畏(methacrifos)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、
二溴磷(naled)、
氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、
甲基一六○五(parathion methyl)、乙基一六○五(parathionethyl)、稻丰散(phenthoate)、三九一一(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、乙丙磷威(phosphocarb)、腈肟磷(phoxim)、虫螨磷(pirimiphos methyl)、乙基虫螨磷(pirimiphos ethyl)、丙溴磷(profenofos)、丙虫磷(propaphos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、发果(prothoate)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、pyridathion、
喹噁磷(quinalphos)、
硫线磷(sebufos)、硫特普(sulfotep)、乙丙硫磷(sulprofos)、
嘧丙磷(tebupirimfos)、双硫磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、triclorfon、
蚜灭多(vamidothion);
2.钠通道调节剂/取决于电位的钠通道阻断剂
2.1拟除虫菊酯类,
例如
氟酯菊酯(acrinathrin)、丙烯除虫菊(d-顺-反、d-反)(allethrin(d-cis-trans,d-trans))、
高效氟氯氰菊酯(beta-cyfluthrin)、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊-S-环戊基异构体、bioethanomethrin、生物氯菊酯(biopermethrin)、右旋反灭虫菊酯(bioresmethrin)、
二氯炔戊菊酯(chlovaporthrin)、顺-氯氰菊酯、顺-灭虫菊(cis-resmethrin)、顺-氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、氯氟氰菊酯(cyhalothrin)、氯氰菊酯(α-、β-、θ-、ζ-)(cypermethrin(alpha-,beta-,theta-,zeta-))、苯醚氯菊酯(cyphenothrin)、
DDT、溴氰菊酯(deltamethrin)、
烯炔菊酯(1R异构体)(empenthrin(1R isomer))、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、
五氟苯菊酯(fenfluthrin)、甲氰菊酯(fenpropathrin)、吡氯氰菊酯(fenpyrithrin)、灭杀菊酯(fenvalerate)、溴氟菊酯(flubrocythrinate)、氟氰戊菊酯(flucythrinate)、氟丙苄醚(flufenprox)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(fluvalinate)、fubfenprox、
γ-氯氟氰菊酯(gamma-cyhalothrin)、
炔咪菊酯(imiprothrin)、
噻嗯菊酯(kadethrin)、
λ-氯氟氰菊酯(lambda-cyhalothrin)、
甲氧苄氟菊酯(metofluthrin)、
氯菊酯(顺-、反-)、苯醚菊酯(1R异构体)(phenothrin(1R-isomer)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、protrifenbute、反灭虫菊(pyresmethrin)、
灭虫菊、RU-15525、
灭虫硅醚(silafluofen)、
氟胺氰菊酯(tau-fluvalinate)、七氟菊酯(tefluthrin)、环戊烯丙菊酯(terallethrin)、胺菊酯(1R反式异构体)(tetramethrin(1R trans-isomer))、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin)、
ZXI 8901、
除虫菊素(pyrethrin)(除虫菊(pyrethrum))、
2.2噁二嗪类(oxadiazine),
例如茚虫威(indoxacarb)
3.乙酰胆碱受体激动剂/拮抗剂
3.1氯烟碱类/新烟碱类(neonicotinoid),例如
吡虫清(acetamiprid)、
噻虫胺(clothianidin)、
呋虫胺(dinotefuran)、
吡虫啉(imidacloprid)、
硝胺烯啶(nitenpyram)、硝虫噻嗪(nithiazine)、
噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)
3.2烟碱(nicotine)、杀虫磺(bensultap)、杀螟丹(cartap)
4.乙酰胆碱受体调节剂
4.1spinosyn类,
例如艾克敌105(spinosad)
5.GABA受控氯离子通道拮抗剂
5.1环二烯有机氯类,
例如
毒杀芬(camphechloro)、氯丹(chlorodane)、硫丹(endosulfan)、林丹(gamma-HCH)、六六六(HCH)、七氯(heptachloro)、林丹(lindane)、甲氧滴滴涕(methoxychloro)
5.2Fiprole类,
例如
乙酞虫睛(acetoprole)、乙虫清(ethiprole)、锐劲特(fipronil)、氟吡唑虫(vaniliprole)
6.氯离子通道活化剂类
6.1Mectin类,
例如
阿维菌素(abamectin、avermectin)、埃玛菌素(emamectin)、甲氨基阿维菌素苯甲酸盐(emamectin-benzoate)、伊维菌素(ivermectin)、弥拜菌素(milbemectin)、米尔倍霉素(milbemycin)
7.保幼激素模拟物类
例如
苯虫醚(diofenolan)、保幼醚(epofenonane)、苯氧威(fenoxycarb)、烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)、烯虫酯(methoprene)、吡丙醚(pyriproxifen)、烯虫硫酯(triprene)
8.蜕皮激素激动剂/干扰剂(disruptor)类
8.1二酰基肼类,
例如
环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)、虫酰肼(tebufenozide)
9.几丁质生物合成抑制剂
9.1苯甲酰脲类,例如
双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟啶蜱脲(fluazuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟幼脲(penfluron)、伏虫磷(teflubenzuron)、杀虫隆(triflumuron)
9.2噻嗪酮(buprofezin)
9.3灭蝇胺(cyromazine)
10.氧化磷酸化抑制剂,ATP干扰剂类
10.1杀螨硫隆(diafenthiuron)
10.2有机锡类,
例如唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨锡(fenbutatin oxide)
11.通过打断H-质子梯度而起作用的氧化磷酸化去偶剂(decoupler)类
11.1吡咯类,
例如氟唑虫清(chlorofenapyr)
11.2二硝基苯酚类,
例如乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、DNOC
12.I位点电子转移抑制剂类
12.1METI类,
例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)
12.2灭蚁腙(hydramethylnone)
12.3开乐散(dicofol)
13.II位点电子转移抑制剂类
13.1鱼藤酮(Rotenone)
14.III位点电子转移抑制剂类
14.1灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)
15.昆虫肠道膜微生物干扰剂类
苏云金杆菌(Bacillus thuringiensis)菌株
16.脂肪合成抑制剂
16.1季酮酸(tetronic acid)类,
例如
螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)
16.2特特拉姆酸(tetramic acid)类,
例如
3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(别名:碳酸-3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]癸-3-烯-4-基乙酯,CAS注册号:382608-10-8)以及顺-3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1-氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(CAS注册号:203313-25-1)
17.甲酰胺类,
例如氟啶虫酰胺(flonicamid)
18.章鱼胺能激动剂类,
例如虫螨脒(amitraz)
19.镁刺激的ATP酶抑制剂类,
例如克螨特(propargite)
20.邻苯二酰胺类,
例如N2-[1,1-二甲基-2-(甲基磺酰基)乙基]-3-碘-N1-[2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]-1,2-苯二甲酰胺(CAS注册号:272451-65-7、flubendiamide)
21.沙蚕毒素类似物,
例如硫赐安(thiocyclam hydrogen oxalate)、杀虫双(thiosultap-sodium)
22.生物制剂类、激素类或信息素类,
例如
艾扎丁(azadirachtin)、芽孢杆菌种(Bacillus spec.)、白僵菌种(Beauveria spec.)、十二碳二烯醇(Codlemone)、绿僵菌种(Metarrhizium spec.)、拟青霉种(Paecilomyces spec.)、敌贝特(Thuringiensin)、轮枝菌种(Verticillium spec.)
23.作用机理未知或未确定的活性化合物类
23.1熏蒸剂类,
例如
磷酸铝、一溴甲烷、硫酰氟
23.2选择性拒食剂类,
例如
冰晶石、氟啶虫酰胺(flonicamid)、拒嗪酮(pymetrozine)
23.3螨生长抑制剂类,
例如
四螨嗪(clofentezine)、特苯噁唑(etoxazole)、噻螨酮(hexythiazox)
23.4amidoflumet、
benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、噻嗪酮(buprofezin)、
灭螨锰、杀虫脒(chlorodimeform)、乙酯杀螨醇(chlorobenzilate)、氯化苦(chloropicrin)、clothiazoben、cycloprene、cyflumetofen、
地昔尼尔(dicyclanil)、
fenoxacrim、氟硝二苯胺(fentrifanil)、噻唑螨(flubenzimine)、flufenerim、氟替阿嗪(flutenzin)、
诱虫十六酯(gossyplure)、
灭蚁腙(hydramethylnone)、
japonilure、
恶虫酮(metoxadiazone)、
石油、
胡椒基丁醚(piperonyl butoxide)、油酸钾、pyrafluprole、啶虫丙醚(pyridalyl)、pyriprole
氟虫胺(sulfluramid)、
三氯杀螨砜(tetradifon)、杀螨好(tetrasul)、苯赛螨(thiarathene)、verbutin,
此外还有化合物丙基氨基甲酸-3-甲基苯基酯(速灭威Z(tsumacide Z))、
化合物3-(5-氯-3-吡啶基)-8-(2,2,2-三氟乙基)-8-氮杂双环[3.2.1]辛烷-3-腈(CAS注册号185982-80-3)及相应的3-内型异构体(CAS注册号185984-60-5)(参见WO 96/37494、WO 98/25923)、
以及含有杀昆虫活性的植物提取物、线虫、真菌或病毒的制剂。
还可以与其他已知活性化合物如除草剂,或者与肥料和生长调节剂、安全剂和/或化学信息化合物混合。
本发明的活性化合物可以其本身或其制剂形式或由其制备的使用形式通过进一步稀释施用,例如即用的溶液剂、乳剂、悬浮剂、粉剂、片剂、膏剂、微胶囊剂和颗粒剂。它们以常规方式使用,例如泼浇、浸渍、喷雾、雾化、弥雾、蒸发、注射、形成浆料、涂抹、喷粉、撒播、干法拌种、润湿法拌种(moist drssing)、湿法拌种、浆料拌种或包壳(encrusting)。
在处理植物部位时,使用形式的活性化合物的浓度可在较宽范围内变化。它们通常为1至0.0001重量%,优选0.5至0.001重量%。
对于种子处理而言,每1千克的种子通常使用的活性化合物的量为0.1至10g,尤其为1至5g。
对于土壤处理而言,通常使用的作用点处的活性化合物浓度为0.00001至0.1重量%,尤其为0.0001至0.02%。
如上所述,可依据本发明处理所有的植物和其部位。在一个优选实施方案中,处理了天然存在的植物种以及植物变种,或由常规生物育种方法,例如由杂交或原生质体融合获得的植物种,以及所述植物的部位。在另一个优选实施方案中,处理了由基因工程方法——可能的话还可与常规方法结合——而获得的转基因植物和植物变种(基因修饰的生物)及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
极其优选依据本发明处理的植物为在任何特定时间市售或使用的植物变种。植物变种应理解为由常规育种、诱变或重组DNA技术育种的具有特定特性(“特征”)的植物。它们可以是变种、生物型(biotype)或基因型。
依据植物种或植物变种、其种植地点和生长条件(土壤、气候、植物生长期和肥料相关的类型),本发明的处理也可产生超加和(“协同”)效应。例如,可获得超过实际预期效果的以下效果:可降低按本发明使用的物质和组合物的施用率和/或加宽其作用谱和/或提高其活性,可改善植物生长、提高高温或低温耐受性、提高干旱耐受性或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高作物产量、提高采收作物的质量和/或改善其营养价值并且改善采收作物的贮存性质和/或其加工性能。
优选根据本发明处理的转基因植物或植物变种(通过基因工程获得)包括在因基因修饰接受了遗传物质的所有植物,所述遗传物质将特别的有利的有用特性(“特征”)赋予所述植物。所述特性的实例包括改善植物生长、提高高温或低温耐受性、提高干旱耐受性或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高作物产量、提高采收作物的质量和/或提高其营养价值并且改善采收作物的贮存性质和/或其加工性能。值得特别注意的所述特性的其他实例包括改善植物对动物和微生物害虫的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提出的转基因植物的实例为重要的作物,例如谷物(小麦和稻)、玉米、大豆、马铃薯、棉花、油菜和果实植物(果实为苹果、梨、柑橘类果实和葡萄),值得特别注意的作物为玉米、大豆、马铃薯、棉花和油菜。特别重要的特性(“特征”)为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c Cry2Ab、Cry3Bb和CryIF及其结合)在植物体内形成的毒素,来提高植物对昆虫的抵抗力(以下简称为“Bt植物”)。特别强调的特性(“特征”)为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。尤其重要的特性(“特征”)还可为提高植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘膦或phosphinotricine(例如“PAT”基因)。赋予所需特性(“特征”)的对应基因也可各自在转基因植物体内相互结合。可提出的“Bt植物”的实例包括市售的商标名称为YI ELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)的玉米、棉花、大豆和马铃薯的变种。可提出的具有除草剂耐受性的植物的实例为市售的商标名称为Roundup Ready(具有草甘膦耐受性,例如玉米、棉花、大豆)、Liberty Link(具有phosphinotricine耐受性,例如油菜)、IMI(具有咪唑啉酮耐受性)和STS(具有磺酰脲耐受性,例如玉米)的玉米、棉花和大豆的变种。可提出的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)还包括名称为Clearfield的市售变种(例如玉米)。当然,以上叙述也适用于具有上述的或在未来开发的基因特性(“特征”)的任何植物变种,所述植物变种将在未来开发或上市。
根据本发明,上述植物可特别有利地用本发明的通式I化合物或本发明的活性化合物混合物进行处理。上述活性化合物或混合物的优选范围也适用于这些植物的处理。特别有利的为用本发明具体列出的化合物或混合物对植物进行处理。
本发明的活性化合物还适用于防治动物害虫。本申请中所称的有害动物表示有害的节肢动物和蠕虫,特别是在农业、森林、贮存产品和材料的保护以及卫生部门中遇到的昆虫、蛛形纲动物和线虫;活性化合物具有良好的植物耐受性,并且具有对温血动物有利的毒性。优选将活性化合物用作植物保护剂。它们对通常敏感和抗性的物种以及全部或某些发育阶段具有活性。上述害虫包括:
等足目(Isopoda),例如,栉水虱(Oniscus asellus)、鼠妇(Armadillidium vulgare)和球鼠妇(Porcellio scaber)。
倍足目(Diplopoda),例如,Blaniulus guttulatus。
唇足目(Chilopoda),例如,Geophilus carpophagus和Scutigeraspp.。
综合目(Symphyla),例如,Scutigerella immaculata。
缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
弹尾目(Collembola),例如,武装棘跳虫(Onychiurus armatus)。
直翅目(Orthoptera),例如,家蟋(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、非洲飞蝗(Locusta migratoriamigratorioides)、黑蝗属(Melanoplus spp.)和沙漠蝗(Schistocercagregaria)。
蜚蠊目(Blattaria),例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaeamaderae)、德国蠊(Blattella germanica)。
革翅目(Dermaptera),例如,欧洲球螋(Forficula auricularia)。
等翅目(Isoptera),例如,散白蚁属(Reticulitermes spp.)。
虱目(Phthiraptera),例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、嚼虱属(Trichodectes spp.)和畜虱属(Damalinia spp.)。
缨翅目(Thysanoptera),例如,温室条篱蓟马(Hercinothripsfemoralis)、烟蓟马(Thrips tabaci)、棕榈蓟马(Thrips palmi)和苜蓿蓟马(Frankliniella accidentalis)。
异翅目(Heteroptera),例如,扁盾蝽属(Eurygaster spp.)、Dysdercus intermedius、方背皮蝽(Piesma quadrata)、温带臭虫(Cimex lectularius)、长红猎蝽(Rhodnius prolixus)和锥猎蝽属(Triatoma spp.)。
同翅目(Homoptera),例如,甘蓝粉虱(Aleurodes brassicae)、木薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、梅大尾蚜(Hyalopterusarundinis)、葡萄根瘤蚜(Phylloxera vastatrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤蚜属(Myzusspp.)、忽布疣蚜(Phorodon humuli)、禾谷缢管蚜(Rhopalosiphumpadi)、小绿叶蝉属(Empoasca spp.)、Euscelis bilobatus、黑尾叶蝉(Nephotettix cincticeps)、水木坚蚧(Lecanium corni)、乌盔蚧(Saissetia oleae)、灰飞虱(Laodelphax striatellus)、褐飞虱(Nilaparvata lugens)、红肾圆盾蚧(Aonidiella aurantii)、常春藤圆盾蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目(Lepidoptera),例如,红铃麦蛾(Pectinophoragossypiella)、松尺蠖(Bupalus piniarius)、冬尺蛾(Cheimatobiabrumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeuta padella)、菜蛾(Plutella xylostella)、黄褐天幕毛虫(Malacosoma neustria)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、埃及金刚钻(Earias insulana)、实夜蛾属(Heliothis spp.)、甘蓝夜蛾(Mamestrabrassicae)、小眼夜蛾(Panolis flammea)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹果小卷蛾(Carpocapsapomonella)、菜粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestia kuehniella)、大蜡螟(Galleria mellonella)、幕谷蛾(Tineola bisselliella)、袋谷蛾(Tinea pellionella)、褐织蛾(Hofmannophilapseudospretella)、亚麻黄卷蛾(Cacoecia podana)、Capuareticulana、枞色卷蛾(Choristoneura fumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homona magnanima)、栎绿卷蛾(Tortrix viridana)、Cnaphalocerus spp.、水稻负泥虫(Oulemaoryzae)。
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum)、谷蠹(Rhizopertha dominica)、恶条豆象(Bruchidius obtectus)、菜豆象(Acanthoscelide sobtectus)、北美家天牛(Hylotrupesbajulus)、杨树萤叶甲(Agelastica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶虫(Phaedon cochleariae)、叶甲属(Diabrotica spp.)、油菜金头跳甲(Psylliodes chrysocephala)、墨西哥大豆瓢虫(Epilachna varivestis)、Atomaria spp.、锯谷盗(Oryzaephilus surinamensis)、花象属(Anthonomus spp.)、谷象属(Sitophilus spp.)、黑葡萄耳象(Otiorrhynchus sulcatus)、香蕉根颈象(Cosmopolites sordidus)、白菜籽龟象(Ceuthorrhynchusassimilis)、紫苜蓿叶象(Hypera postica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛皮蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、叩甲属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon solstitialis)、褐新西兰肋翅鳃角金龟(Costelytra zealandica)和稻根象(Lissorhoptrus oryzophilus)。
膜翅目(Hymenoptera),例如,松叶蜂属(Diprion spp.)、实叶蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小家蚁(Monomoriumpharaonis)和胡蜂属(Vespa spp.)。
双翅目(Diptera),例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、库蚊属(Culex spp.)、黑尾果蝇(Drosophila melanogaster)、家蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Calliphoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyiaspp.)、黄蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、Hyppobosca spp.、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、Tannia spp.、Bibio hortulanus、瑞典麦秆蝇(Oscinella frit)、草种蝇属(Phorbiaspp.)、藜泉蝇(Pegomyia hyoscyami)、地中海蜡实蝇(Ceratitiscapitata)、橄榄大实蝇(Dacusoleae)、欧洲大蚊(Tipula paludosa)、黑蝇属(Hylemyia spp.)和斑潜蝇属(Liriomyza spp.)。
蚤目(Siphonaptera),例如,印鼠客蚤(Xenopsylla cheopis)和角叶蚤属种(Ceratophyllus spp.)。
蛛形纲(Arachnida),例如,中东金蝎(Scorpio maurus)、黑寡妇蜘蛛(Latrodectus mactans)、粗脚粉螨(Acarus siro)、锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssus gallinae)、茶藨瘿螨(Eriophyes ribis)、桔芸锈螨(Phyllocoptruta oleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、痒螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)、叶螨属(Tetranychus spp.)、半跗线螨属(Hemitarsonemus spp.)、短须螨属(Brevipalpus spp.)。
植物寄生线虫包括,例如,短体线虫属(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、起绒草茎线虫(Ditylenchusdipsaci)、半穿刺线虫(Tylenchulus semipenetrans)、异皮线虫属(Heterodera spp.)、球异皮线虫属(Globodera spp.)、根结线虫属(Meloidogyne spp.)、滑刃线虫属(Aphelenchoides spp.)、长针线虫属(Longidorus spp.)、剑线虫属(Xiphinema spp.)、毛刺线虫属(Trichodorus spp.)、伞滑刃线虫属(Bursaphelenchusspp.)。
如果合适,本发明的化合物也可以一定的浓度或施用率用作除草剂和杀微生物剂,例如杀真菌剂、抗霉菌剂和杀细菌剂。如果合适,它们还可用作合成其它活性化合物的中间体或前体。
所有的植物及植物部位均可依据本发明来处理。本发明中植物的含义应理解为所有的植物和植物种群,例如需要的和不需要的野生植物或作物(包括自然存在的作物)。作物可以是通过常规植物育种和优选法,或通过生物技术和重组方法,或通过前述方法的结合而获得的植物,包括转基因植物,也包括受植物种苗权保护或不受其保护的植物栽培种。植物部位的含义应理解为植物的所有地上及地下部位和器官,例如芽、叶、花和根,可提出的实例有叶、针叶、茎、干、花、子实体(fruit body)、果实、种子、根、块茎和根茎。植物部位还包括采收物,以及无性和有性繁殖物,例如插条、块茎、根茎、短匐茎和种子。
本发明的使用活性化合物对植物和植物部位进行的处理,通过常规处理方法直接进行或使化合物作用于环境、生境或贮存空间,所述常规处理方法包括例如浸渍、喷雾、蒸发、弥雾(fogging)、撒播、涂抹(painting on),并且在繁殖物特别是种子的情况下,还可施用一层或多层涂布。
本发明的活性化合物可转化为常规制剂,例如溶液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、粉末剂、膏剂、可溶性粉剂、颗粒剂、悬乳浓缩剂、用活性化合物浸渍过的天然和合成材料、以及聚合物中的微胶囊剂。
这些制剂以已知方式制备,例如将活性化合物与填充剂混合,即与液体溶剂和/或固体载体混合,同时可任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
若使用的填充剂为水,还可例如使用有机溶剂作为助溶剂。以下基本上适用作液体溶剂:芳香族化合物,例如二甲苯、甲苯或烷基萘;氯代芳香族化合物或氯代脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷或石蜡,如石油馏分、矿物油和植物油;醇,例如丁醇或乙二醇及其醚和酯;酮,例如丙酮、甲乙酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲基亚砜;以及水。
适合的固体载体包括:
例如铵盐,粉碎的天然矿物例如高岭土、粘土、滑石、白垩、石英、凹凸棒石、蒙脱石或硅藻土,以及粉碎的合成材料例如高度分散的二氧化硅、氧化铝和硅酸盐;适用于颗粒剂的固体载体包括:例如粉碎并分级的天然岩石例如方解石、大理石、浮石、海泡石和白云石,和合成的无机和有机粉颗粒,以及有机物颗粒例如锯木屑、椰壳、玉米穗轴和烟草茎;适合的乳化剂和/或发泡剂包括:例如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚例如烷基芳基聚乙二醇醚,烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物;适合的分散剂包括:例如木素亚硫酸盐废液和甲基纤维素。
制剂中可使用增粘剂,例如羧甲基纤维素,以及粉末、颗粒或胶乳状的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂例如脑磷脂和卵磷脂,以及合成磷脂。其他添加剂可以是矿物油和植物油。
可使用着色剂,例如无机颜料例如氧化铁、氧化钛和普鲁士蓝,以及有机着色剂例如茜素着色剂、偶氮着色剂和金属酞菁着色剂,以及微量营养素例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂通常包括0.1至95重量%、优选0.5至90重量%的活性化合物。
本发明的活性化合物也可以其本身或其制剂的形式与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀昆虫剂混合使用以拓宽作用谱或者防止产生抗性。在许多情况下产生协同效应,即混合物的药效超过各组分的药效。
混合物中共存组分的有利实例为以上所列的、在式(I)化合物杀真菌应用的情形下可能用作混合组分的化合物。
还可以混合其他已知的活性化合物,例如除草剂、肥料以及生长调节剂。
本发明的活性化合物以其市售制剂以及由市售制剂制备的使用形式用作杀昆虫剂时,还可以与增效剂的混合物的形式存在。增效剂为通过其加入可提高活性化合物活性、而其本身不一定具有活性的化合物。
由市售制剂制备的使用形式的活性化合物含量可在较宽的限度内变化。使用形式的活性化合物浓度可为0.0000001至95重量%的活性化合物,优选0.0001至1重量%。
它们以适合于使用形式的常规方式施用。
用于防治卫生害虫和贮存物品害虫时,本发明的活性化合物在以下两方面表现突出,即,木材和粘土上的优良的残留作用,以及对石灰基质上的碱的良好稳定性。
如上所述,可依据本发明处理所有的植物和其部位。在一个优选实施方案中,处理了野生植物种以及植物栽培种,或由常规生物育种方法,例如由杂交或原生质体融合获得的植物种,以及上述各植物种的部位。在另一个优选实施方案中,处理了由基因工程——如果合适还可与常规方法结合——而获得的转基因植物和植物栽培种(基因修饰的生物)及其部位。术语“部位”或“植物的部位”或“植物部位”解释如上。
特别优选依据本发明处理的植物为各自市售或使用的植物栽培种。植物栽培种的含义应理解为由常规栽培、诱变或重组DNA技术生长的具有新特性(“特征”)的植物。它们可以是栽培种、生物型或基因型。
依据植物种或植物栽培种、其种植地点和生长条件(土壤、气候、植物生长期、营养),本发明的处理也可产生超加和(“协同”)效应。由此,例如,可获得超过实际预期效果的以下效果:可降低按本发明使用的物质和组合物的施用率和/或加宽其作用谱和/或提高其活性,可改善植物生长、提高高温或低温耐受性、提高干旱耐受性或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、提高采收产品的质量和/或改善其营养价值、改善采收产品的贮存稳定性和/或其加工性能。
优选根据本发明处理的转基因植物或植物栽培种(即通过基因工程获得)包括在遗传修饰中接受了遗传物质的所有植物,所述遗传物质将特别的有利的有用特性(“特征”)赋予所述植物。所述特性的实例包括改善植物生长、提高高温或低温耐受性、提高干旱耐受性或水或土壤含盐量耐受性、提高开花品质、使采收更简易、加速成熟、提高产量、提高采收产品的质量和/或提高其营养价值、改善采收产品的贮存稳定性和/或其加工性能。需特别强调的所述特性的其他实例包括改善植物对动物和微生物害虫的抵抗力,例如对昆虫、螨虫、植物致病真菌、细菌和/或病毒的抵抗力,以及提高植物对某些除草活性化合物的耐受性。可提出的转基因植物的实例包括重要的作物,例如谷物(小麦、稻)、玉米、大豆、马铃薯、棉花、油菜(oilseed rape)和果实植物(果实为苹果、梨、柑橘类果实和葡萄),特别强调玉米、大豆、马铃薯、棉花和油菜。特别强调的特性为通过在植物体内形成毒素,特别是由苏云金杆菌的遗传物质(例如基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其结合)在植物体内形成的毒素,来提高植物对昆虫的抵抗力(以下简称为“Bt植物”)。特别强调的其他特性为通过系统获得性抗性(SAR)、系统素、植物抗毒素、引发物和抗性基因以及相应的表达蛋白质和毒素来提高植物对真菌、细菌和病毒的抵抗力。另外尤其强调的特性为提高植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘膦或phosphinotricin(例如“PAT”基因)。赋予所需特性的基因也可在转基因植物体内相互结合。可提出的“Bt植物”的实例包括市售的商标名称为YIELD GARD(例如玉米、棉花、大豆)、KnockOut(例如玉米)、StarLink(例如玉米)、Bollgard(棉花)、Nucotn(棉花)和NewLeaf(马铃薯)的玉米变种、棉花变种、大豆变种和马铃薯变种。可提出的具有除草剂耐受性的植物的实例为市售的商标名称为Roundup Ready(具有草甘膦耐受性,例如玉米、棉花、大豆)、Liberty Link(具有phosphinotricin耐受性,例如油菜)、IMI(具有咪唑啉酮耐受性)和STS(具有磺酰脲耐受性,例如玉米)的玉米变种、棉花变种和大豆变种。可提出的具有除草剂抗性的植物(以常规的除草剂耐受性方式育种的植物)还包括名称为Clearfield的市售变种(例如玉米)。当然,以上叙述也适用于具有所述基因特性或待开发基因特性的植物栽培种,所述植物栽培种将在未来开发和/或上市。
上述植物可特别有利地用本发明的式I化合物或本发明的活性化合物混合物进行处理。上述活性化合物或混合物的优选范围也适用于这些植物的处理。特别强调的为用本发明具体提出的化合物或混合物对植物进行处理。
本发明的活性化合物不仅对植物害虫、卫生害虫和贮存物品害虫具有活性,而且在兽医领域对动物寄生虫(体外寄生虫)例如硬蜱、软蜱、疥螨、叶螨、蝇(叮咬和吸食)、寄生蝇幼虫、虱、毛虱、羽虱和蚤也具有活性。这些寄生虫包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phtirus spp.和管虱属(Solenopotes spp.)。
食毛目(Mallophagida)及钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menoponspp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、嚼虱属(Trichodectes spp.)和猫羽虱属(Felicola spp.)。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culexspp.)、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitraspp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxysspp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphoraspp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrusspp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)和蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉首蚤属(Ctenocephalides spp.)、客蚤属(Xenopsylla spp.)和角叶蚤属(Ceratophyllus s p.)。
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatoma spp.)、红猎蝽属(Rhodnius spp.)和锥蝽属(Panstrongylus spp.)。
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国蠊(Blattela germanica)和夏柏拉蟑螂属(Supella spp.)。
蜱螨亚纲(Acarica或Acarida)及后气门目(Metastigmata)和中气门目(Mesostigmata),例如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.)、硬蜱属(Ixodesspp.)、花蜱属(Amblyomma spp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、Haemophysalis spp.、璃眼蜱属(Hyalommaspp.)、扇头蜱属(Rhipicephalus spp.)、皮刺螨属(Dermanyssusspp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)和蜂螨属(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapisspp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletiaspp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、耳疥螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、耳螨属(Notoedres spp.)、疙螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)和鸡雏螨属(Laminosioptes spp.)。
本发明的式(I)活性化合物也适用于防治侵害下列动物的节肢动物:农业牲畜,例如黄牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂;其他玩赏动物,例如狗、猫、笼鸟和观赏鱼;以及所谓的试验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治这些节肢动物可减少死亡数和减产量(肉、奶、毛、皮、蛋、蜜等),从而可通过使用本发明的活性化合物使畜牧养殖更经济更简便。
在兽医领域中,本发明的活性化合物以已知方式使用,可通过例如片剂、胶囊、口服饮剂、浸剂、颗粒、膏剂、丸剂、喂服(feed-through)法、栓剂的方式进行肠内给药,可通过例如注射(肌肉注射、皮下注射、静脉注射、腹膜内注射等)、植入的方式进行肠外给药,可鼻部给药,可通过例如浸泡或浸洗、喷雾、泼浇和点滴、清洗和喷粉的形式,并借助于含有活性化合物的模型制品例如项圈、耳标、尾标、肢体缚带(limb band)、笼头、标识器等进行皮肤给药。
向家畜、家禽、玩赏动物等给药时,本发明的式(I)活性化合物可以含有l至80重量%活性化合物的制剂(例如粉剂、乳剂、流动性组合物)形式直接使用,也可稀释100至10000倍后使用,或以化学药浴剂(chemical bath)形式使用。
此外,已发现本发明的化合物对毁坏工业材料的昆虫表现出强的杀昆虫活性。
以优选的、非限制性的实例的方式可提出下列昆虫:
甲虫,例如北美家天牛、Chlorophorus pilosis、家具窃蠹、报死窃蠹(Xestobium rufovillosum)、梳角细脉窃蠹(Ptilinuspecticornis)、Dendrobium pertinex、松窃蠹(Ernobiu smollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctusafricanus)、南方粉蠹(Lyctus planicollis)、栎粉蠹(Lyctuslinearis)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthes rugicollis)、材小蠹种(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、褐异翅长蠹(Heterobostrychus brunneus)、棘长蠹种(Sinoxylon spec.)、竹长蠹(Dinoderus minutus)。
膜翅目昆虫,例如大树蜂(Sirex juvencus)、枞大树蜂(Urocerusgigas)、泰加大树蜂(Urocerus gigas taignus)、Urocerus augur。
白蚁,例如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、灰点异白蚁(Heterotermes indicola)、欧美散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、南欧网纹白蚁(Reticulitermeslucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsis nevadensis)、家白蚁(Coptotermesformosanus)。
蠹虫,例如衣鱼。
本发明中工业材料的含义应理解为非活体(non-living)材料,例如,优选塑料、胶粘剂、胶液、纸张和板材、皮革、木材、木材产品和涂料组合物。
待保护以免受昆虫侵害的材料特别优选木材及加工过木材产品。
可由本发明的试剂或含有所述试剂的混合物保护的木材及加工过的木材产品的含义应理解为,例如:
建筑木材、木梁、铁路枕木、桥梁组件、突堤、木制交通工具、箱、托架、集装箱、电线杆、木制包层、木制门窗、胶合板、刨花板、细木工制品,或常用于房屋建造或建筑木工中的木材产品。
本发明的活性化合物可直接使用、以浓缩物形式使用或以一般常规制剂形式使用,例如粉剂、颗粒剂、溶液剂、悬浮剂、乳剂或膏剂。
上述制剂可以本身已知的方式制备,例如将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂混合,如果合适还可与干燥剂及UV稳定剂混合,并且如果合适也可与着色剂、颜料及其它处理助剂混合。
用于保护木材及木材制品的杀昆虫组合物或浓缩物中包括浓度为0.0001至95重量%、特别是0.001至60重量%的本发明活性化合物。
组合物或浓缩物的用量取决于昆虫的种类和出现率以及介质。最佳施用量可分别通过一系列试验而确定。但一般而言,以待保护的材料计,使用0.0001至20重量%、优选0.001至10重量%的活性化合物就已足够。
所用的溶剂和/或稀释剂为有机化学溶剂或溶剂混合物,和/或低挥发性油性或油状有机化学溶剂或溶剂混合物,和/或极性有机化学溶剂或溶剂混合物,和/或水,如果合适还有乳化剂和/或润湿剂。
优选使用的有机化学溶剂为蒸发值(evaporation number)高于35、闪点高于30℃、优选高于45℃的油性或油状溶剂。用作不溶于水的低挥发性油性及油状溶剂的物质为适合的矿物油或其芳香性馏分,或含矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
有利地使用的物质为沸程170至220℃的矿物油、沸程170至220℃的石油溶剂、沸程250至350℃的锭子油、沸程160至280℃的石油和芳香化合物、松节油等等。
在一个优选实施方案中,使用沸程180至210℃的液态脂族烃,或沸程180至220℃的芳香烃与脂族烃的高沸点混合物、和/或锭子油、和/或一氯代萘,优选α-一氯代萘。
蒸发值高于35且闪点高于30℃、优选高于45℃的低挥发性有机油性或油状溶剂,可以部分地用高挥发性或中等挥发性的有机化学溶剂代替,只要溶剂混合物也具有高于35的蒸发值和高于30℃、优选高于45℃的闪点,并且所述杀昆虫/杀真菌混合物在该溶剂混合物中可溶或可乳化。
在一个优选实施方案中,一部分有机化学溶剂或溶剂混合物、或脂族极性有机化学溶剂或溶剂混合物被代替。优选使用的物质为含羟基和/或酯基和/或醚基的脂族有机化学溶剂,例如乙二醇醚、酯等。
在本发明范围内使用的有机化学粘合剂为:合成树脂;和/或可用水稀释和/或可在所用的有机化学溶剂中溶解或分散或乳化的本身已知的粘合干性油(binding drying oil),特别是由以下物质组成、或包括以下物质的粘合剂:丙烯酸酯树脂,乙烯基树脂例如聚乙酸乙烯酯,聚酯树脂,缩聚或加聚树脂,聚氨酯树脂,醇酸树脂或改性醇酸树脂,酚树脂,烃类树脂例如茚/苯并呋喃树脂,硅氧烷树脂,干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干性粘合剂。
用作粘合剂的合成树脂可以乳液、分散液或溶液形式使用。最高为10重量%的沥青或沥青类物质也可用作粘合剂。此外,还可使用本身已知的着色剂、颜料、防水剂、遮味剂和抑制剂或防蚀剂等等。
依据本发明,组合物或浓缩物优选包括至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为有机化学粘合剂。本发明优选使用油含量高于45重量%、优选50至68重量%的醇酸树脂。
上述粘合剂的一部分或全部可以被固定剂(混合物)或增塑剂(混合物)代替。这些添加剂旨在防止活性化合物的挥发、以及结晶或沉淀。它们优选代替0.01至30%的粘合剂(以所使用的粘合剂为100%计)。
增塑剂来自于以下化学类别:邻苯二甲酸酯,例如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苯甲基丁基酯;磷酸酯,例如磷酸三丁酯;己二酸酯,例如己二酸二(2-乙基己基)酯;硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯;油酸酯,例如油酸丁酯;丙三醇醚或较高分子量的乙二醇醚、丙三醇酯和对甲苯磺酸酯。
固定剂在化学上基于聚乙烯烷基醚例如聚乙烯甲基醚,或基于酮例如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂还有水,如果合适可将水与一种或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂混合。
特别有效的木材保护通过大规模的工业浸渍工艺完成,例如真空、双真空或压力工艺。
如果合适,即用的组合物还可另外包括其它杀昆虫剂,如果合适还包括一种或多种杀真菌剂。
可混合的适合的其它组分优选为WO 94/29268中提到的杀昆虫剂和杀真菌剂。该文献中提到的化合物明确地为本申请的一部分。
可提出的尤其优选的混合组分为杀昆虫剂,例如毒死蜱、腈肟磷、silafluofin、顺式氯氰菊酯(alphamethrin)、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、NI-25、氟虫脲、氟铃脲、四氟菊酯、噻虫啉、甲氧苯酰肼(methoxyphenoxide)和杀虫隆,
以及杀真菌剂,例如氧唑菌(epoxyconazole)、己唑醇、氧环唑、丙环唑、戊唑醇、环丙唑醇、叶菌唑、抑霉唑、苯氟磺胺、甲苯氟磺胺、氨基甲酸-3-碘-2-丙炔基丁基酯、N-辛基异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明的化合物可同时用于保护与盐水或半咸水接触的物体,特别是船体、筛、网、建筑物、系留和信号系统,以防产生污垢。
由固着性的寡毛纲(Oligochaeta)动物、例如龙介虫科(Serpulidae),以及由贝壳(shell)及Ledamorpha类(鹅茗荷(goosebarnacles))的种、例如不同的茗荷属(Lepas)及铠茗荷属(Scalpellum)种,或由藤壶(Balanomorpha)类(藤壶(acornbarnacles))的种、例如藤壶属(Balanus)或龟足属(Pollicipes)种引起的污垢,会提高船只的摩擦阻力,从而导致由于高能耗和干船坞中额外的频繁滞留而产生的运转成本的显著增加。
除藻类例如水云种(Ectocarpus sp.)和角藻种(Ceramium sp.)引起的污垢之外,由归入总称为蔓足纲(Cirripedia)(cirripedcrustaceans)的固着性的Entomostraka类引起的污垢亦特别重要。
出人意料的是,现已发现单独的本发明化合物、或其与其它活性化合物的结合具有突出的防污活性。
单独使用或与其它活性化合物结合使用本发明的化合物,可以避免使用下述化合物中的重金属,或显著降低这些化合物的使用浓度,所述化合物包括例如,双(三烷基锡)硫化物,月桂酸三正丁基锡,氯化三正丁基锡,氧化亚铜(I),氯化三乙基锡,三正丁基(2-苯基-4-氯苯氧基)锡,氧化三丁基锡,二硫化钼、氧化锑、钛酸丁酯聚合物、苯基(双吡啶)三氯化铋,氟化三正丁基锡、亚乙基双硫代氨基甲酸锰,二甲基二硫代氨基甲酸锌、亚乙基双硫代氨基甲酸锌、2-吡啶硫醇1-氧化物的锌盐和铜盐、双二甲基二硫代氨基甲酰锌的亚乙基双硫代氨基甲酸盐(bisdimethyldithiocarbamoylzincethylenebisthiocarbamate)、氧化锌、亚乙基双二硫代氨基甲酸亚铜(I)、硫氰酸铜、环烷酸铜和卤化三丁基锡。
如果合适,即用的防污漆还可另外包括其它活性化合物,优选杀藻剂、杀真菌剂、除草剂、杀软体动物剂或其它防污活性化合物。
与本发明防污组合物结合的优选的适合组分包括:
杀藻剂,例如
2-叔丁基氨基-4-环丙基氨基-6-甲硫基-1,3,5-三嗪、双氯酚、敌草隆(diuron)、草藻灭(endothal)、薯瘟锡(fentin acetate)、异丙隆(isoproturon)、噻唑隆(methabenzthiazuron)、氟硝草醚(oxyfluorfen)、灭藻醌(quinoclamine)及去草净(terbutryn);
杀真菌剂,例如
苯并[b]噻吩羧酸环己基酰胺S,S-二氧化物、苯氟磺胺、fluorfolpet、氨基甲酸3-碘-2-丙炔基丁基酯、甲苯氟磺胺,以及吡咯类,例如
氧环唑、环丙唑醇、氧唑菌、己唑醇、叶菌唑、丙环唑和戊唑醇;
杀软体动物剂,例如
薯瘟锡、四聚乙醛、灭虫威(methiocarb)、杀螺胺、硫双威和混杀威;
或常规的防污活性化合物,例如
4,5-二氯-2-辛基-4-异噻唑啉-3-酮、二碘甲基paratryl砜、2-(N,N-二甲基硫代氨甲酰基硫代)-5-硝基噻唑、2-吡啶硫醇1-氧化物的钾盐、铜盐、钠盐和锌盐、吡啶三苯基甲硼烷、四丁基二锡环氧乙烷、2,3,5,6-四氯-4-(甲磺酰基)吡啶、2,4,5,6-四氯间苯二腈、二硫化四甲基秋兰姆和2,4,6-三氯苯基马来酰亚胺。
使用的防污组合物包括0.001至50重量%、特别是0.01至20重量%浓度的本发明化合物的本发明活性化合物。
此外,本发明的防污组合物还包括常规组分,例如Ungerer,Chem.Ind.1985,37,730-732以及Williams,Antifouling MarineCoatings,Noyes,Park Ridge,1973中所述的成分。
除本发明的杀藻、杀真菌、杀软体动物活性化合物和杀昆虫活性化合物之外,防污漆还包括特别是粘合剂。
公认的粘合剂的实例为,溶剂体系中的聚氯乙烯,溶剂体系中的氯化橡胶,溶剂体系、特别是含水体系中的丙烯酸树脂,水分散体形式或有机溶剂体系形式的氯乙烯/乙酸乙烯酯共聚物体系,丁二烯/苯乙烯/丙烯腈橡胶,干性油例如亚麻子油,树脂酯或与焦油或沥青、柏油和环氧化合物相结合的改性硬化树脂,少量的氯橡胶(chlorinerubber)、氯化聚丙烯和乙烯树脂。
如果合适,漆还包括优选不溶于盐水的无机颜料、有机颜料或着色剂。漆可进一步含有使活性化合物控释的材料,例如松香。此外,所述漆还可包括增塑剂、影响流变学特性的改性剂及其它常规成分。本发明的化合物或上述混合物也可包含于自抛光防污体系中。
本发明的活性化合物亦适于防治封闭空间内发现的动物害虫,特别是昆虫、蛛形纲动物和螨虫,所述封闭空间包括例如住所、工厂车间、办公室、交通工具工作间(vehicle cabin)等。它们可单独或与其它活性化合物以及助剂结合用在防治这些害虫的家用杀昆虫产品中。它们对敏感和抗性物种及全部发育阶段均具有活性。所述害虫包括:
蝎目(Scorpionidea),例如,地中海黄蝎(Buthus occitanus)。
蜱螨目(Acarina),例如,波斯锐缘蜱(Argas persicus)、鸽锐缘蜱(Argas reflexus)、苔螨亚种(Bryobia ssp.)、鸡皮刺螨、家嗜甜螨(Glyciphagus domesticus)、非洲钝缘蜱(Ornithodorusmoubat)、血红扇头蜱(Rhipicephalus sanguineus)、阿氏真恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、特嗜皮螨(Dermatophagoides pteronissimus)、法嗜皮螨(Dermatophagoides forinae)。
蜘蛛目(Araneae),例如,捕鸟蛛(Aviculariidae)、圆蛛(Araneidae)。
盲蛛目(Opiliones),例如,螯蝎(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、长踦盲蛛(Opiliones phalangium)。
等足目,例如,栉水虱、球鼠妇。
倍足目,例如,Blaniulus guttulatus、山蛩虫属(Polydesmusspp.)。
唇足目,例如,地蜈蚣(Geophilus spp.)。
衣鱼目(Zygentoma),例如,栉衣鱼属(Ctenolepisma spp.)、衣鱼、盗火虫(Lepismode sinquilinus)。
蜚蠊目,例如,东方蜚蠊、德国蠊、亚洲蠊(Blattella asahinai)、马德拉蜚蠊、角腹蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、澳洲大蠊(Periplaneta australasiae)、美洲大蠊、大褐大蠊(Periplaneta brunnea)、烟色大蠊(Periplaneta fuliginosa)、棕带蜚蠊(Supella longipalpa)。
跳跃亚目(Saltatoria),例如,家蟋。
革翅目,例如,欧洲球螋。
等翅目,例如,木白蚁属(Kalotermes spp.)、散白蚁属。
啮虫目(Psocoptera),例如,Lepinatus spp.、粉啮虫属(Liposcelis spp.)。
鞘翅目,例如,圆皮蠹属、毛皮蠹属、皮蠹属、长头谷盗(Latheticusoryzae)、隐跗郭公虫属(Necrobia spp.)、蛛甲属、谷蠹、谷象(Sitophilus granarius)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais)、药材甲(Stegobium paniceum)。
双翅目,例如,埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、带喙伊蚊(Aedes taeniorhynchus)、按蚊属、红头丽蝇、高额麻虻(Chrysozona pluvialis)、五带淡色库蚊(Culexquinquefasciatus)、尖音库蚊(Culexpipiens)、环喙库蚊(Culextarsalis)、果蝇属(Drosophila spp.)、夏厕蝇(Fannia canicularis)、家蝇(Musca domestica)、白蛉属、Sarcophaga carnaria、蚋属、厩螫蝇(Stomoxys calcitrans)、欧洲大蚊。
鳞翅目,例如,小蜡螟(Achroia grisella)、大蜡螟、印度谷螟(Plodia interpunctella)、木塞谷蛾(Tinea cloacella)、袋谷蛾、幕谷蛾。
蚤目,例如,犬栉首蚤(Ctenocephalides canis)、猫栉首蚤(Ctenocephalides felis)、人蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤。
膜翅目,例如,广布弓背蚁(Camponotus herculeanus)、黑臭蚁(Lasius fuliginosus)、黑蚁(Lasius niger)、Lasius umbratus、小家蚁、Paravespula spp.、铺道蚁(Tetramorium caespitum)。
虱目(Anoplura),例如,头虱(Pediculus humanus capitis)、体虱、阴虱(Phthirus pubis)。
异翅目,例如,热带臭虫(Cimex hemipterus)、温带臭虫、长红猎蝽、侵扰锥猎蝽(Triatoma infestans)。
它们可单独或与其他适合的活性化合物——例如磷酸酯、氨基甲酸酯、拟除虫菊酯、生长调节剂或其他已知种类杀昆虫剂的活性化合物——相结合用于家用杀昆虫剂领域。
它们用于气雾剂、无压喷雾(pressure-free spray)产品例如泵喷雾剂以及雾化(atomizer)喷雾剂、自动弥雾系统、烟雾发生器、泡沫、凝胶、具有纤维素或聚合物制成的蒸发器用片剂(evaporatortablet)的蒸发器产品、液体蒸发器、凝胶和薄膜蒸发器、推进剂驱动的蒸发器、无动力或无源(passive)蒸发系统、捕蛾纸、捕蛾袋和捕蛾胶中,以颗粒剂或粉剂的形式用于抛撒的饵料中或用于毒饵站(bait station)中。
实施例
本说明书中使用以下缩写
ACN 乙腈
aq. 水性的
DCI 直接化学电离
DCM 二氯甲烷
DMF N,N-二甲基甲酰胺
DMSO 二甲亚砜
EDTA 乙二胺四乙酸
ESI 电喷雾电离
FCS 胎牛血清
h 一小时/数小时
HPLC 高压液相色谱
LC/MS 液相色谱-质谱联用
min 分钟
MS 质谱
NMR 核磁共振谱
PBS 磷酸缓冲盐水
RP 反相(HPCL)
Rt 保留时间(HPLC)
rt 室温
SDS 十二烷基硫酸钠
TFA 三氟乙酸
THF 氢呋喃
UV 紫外光
UV/Vis 紫外-可见光
%的某物 %理论产率
总的实验方法
化学品为购自Merck(Darmstadt,德国)或Sigma-Aldrich(Deisenhofen,德国)的分析级试剂。NMR光谱使用Bruker DRX 500光谱仪(以500.13MHz质子频率运行)在DMSO-d6中记录。
HPLC-MS分析基于对前述方法(M.Stadler等,Phytochemistry,56,787-793)的微小改进以正和负电喷雾电离(ESI)模式使用与LCT质谱计(Micromass,Manchester,UK)联用的安捷伦HP1100液相色谱仪进行。将Waters对称柱用作固定相。流动相A:水中的0.1%甲酸,流动相B:乙腈中的0.1%甲酸;梯度:0~1分钟为100%A,1~6分钟变为90%B,6~8分钟变为100%B,8~10分钟为100%B。在150至1.600之间的分子量范围内记录LC-MS光谱。
HPLC-UC/Vis分析以类似于M.Stadler等,Mycol.Res.,2001,105,1190-1205的方式使用HP 1100系列的HPLC分析系统(安捷伦,Waldbronn,德国)进行,所述HPLC系统包括一个G 1312A二元泵系统、一个G 1315A二极管阵列检测器、一个G 1316A柱室、一个G 1322A脱气装置和一个G 1313A自动注射器。选择0.01%膦酸:乙腈作为流动相,而Merck(Darmstadt,德国)Lichrospher RP 18柱(125×4mm,粒径7μm)作为固定相。在40℃以1ml/min流速以如下梯度分析等分试样(根据主要代谢物的浓度,代表2-10μg可溶于甲醇的物质):在10分钟内从0%乙腈线性变化至100%乙腈,之后保持100%乙腈5分钟;接着使柱再生5分钟。在210nm处以550nm的参考波长和80nm的带宽记录HPLC-UV色谱。使用二极管阵列检测(DAD)在210-600nm范围内记录HPLC-UV/Vis光谱。HP ChemStation软件便于在粗提物(crude extract)中自动搜索已校准的标准化合物。
制备性HPLC使用制备性HPLC系统(Gilson Abimed,Ratingen,德国)在室温下使用下述不同的梯度和固定相实施,所述制备性HPLC系统包括Gilson Unipoint软件、306二元泵系统、205馏分收集器、119UV-Vis检测器、806测压模块以及811C动态混合器。
NMR光谱使用以500.13MHz质子频率运行的Bruker DMX500记录。所有光谱均在302K的DMSO-d6溶液中测量。溶剂峰用作质子和碳的化学位移(δH∶2.50,δC∶39.5)的内参比。
JS360菌株的表征与保存
培养基
酵母-麦芽-葡萄糖(YMG)培养基:D-葡萄糖0.4%、麦芽精(maltextract)1%、酵母膏(yeast extract)0.4%、pH7.2。
Q6培养基:D-葡萄糖0.5%、甘油2%、棉籽粉1%、碳酸钙0.1%、自来水,未调节pH。
C培养基:D-葡萄糖1%、酵母膏1%、NZ胺(Sheffield Chemicals,Sheffield,U.K.,Lot ONA 202)0.5%、可溶性淀粉2%、用碳酸钠将pH调节至7.2后加入碳酸钙0.4%。
GS培养基:D-葡萄糖2%、脱脂豆粕(soymeal)(Soyamin 50T,Degussa,Düsseldorf,德国)2%、可溶性淀粉2%、碳酸钙0.5%、氯化钠0.25%、硫酸镁0.05%、磷酸二氢钾0.025%,pH调节至6.5-6.8。
MC培养基:D-葡萄糖1%、酵母膏0.5%、脱脂豆粕(Soyamin 50T,Degussa,Düsseldorf,德国)1%、可溶性淀粉1%、氯化钠0.5%、碳酸钙0.3%,pH调节至7.2(0.1N氢氧化钠溶液)。
MCPM培养基:Diamalt Maltzin hell(Meistermarken GmbH,Bremen,德国)3.5%、NZ胺(Sheffield Chemicals,Sheffield,U.K.,Lot ONA 202)1%、氯化钠0.3%、磷酸二氢钾0.1%、硫酸镁0.05%、硫酸亚铁0.01%,pH6.8。
MS培养基:甘露醇2%、脱脂豆粕(Soyamin 50T,Degussa,Düsseldorf,德国)2%、碳酸钙0.3%,pH调节至7.5。
SP培养基:甘露醇3%、酵母膏0.75%、可溶性淀粉0.2%、豆蛋白胨(Merck,Darmstadt,德国#107212.0500)0.5%,pH调节至6.0(盐酸)。
JS360菌株从在日本采集的土壤样品中获取。它在拜尔农作物科学股份公司的菌种保藏处(Wuppertal,德国)于液氮下保存在10%的甘油中。它还于2002年11月27日保藏至DSMZ(Deutsche Sammlungfür Mikroorganismen und Zellkulturen,Mascheroder Weg 1b,D-38124Braunschweig,德国),保藏号为DSM 15324。
在YMG培养基上培养12天后,JS360菌株的单个菌落的直径达到24mm。菌落发育为白色的、绒毛状气生菌丝体,而基内菌丝体为微乳状(creamish)。培养物的背面(reverse)为红棕色,并且有微红色的色素释放到培养基中。
JS360菌株的发酵与提取
1:种子培养
将2ml 10%甘油培养物用于接种含有150ml无菌YMG培养基的1升锥形瓶,并在28℃、240rpm的旋转振荡器上繁殖72-96小时。
2:烧瓶规模下JS360菌株的发酵
将JS360菌株从生长良好的YMG种子培养物中接种(每个烧瓶有10ml接种物)后,使其在10个含有150ml Q6培养基(参见上面的描述)的1升锥形瓶中繁殖并在28℃、240rpm的旋转振荡器上繁殖118小时。在发酵过程中,每天取样。测定pH,并使用拜尔DiastixHarnzuckerstreifen估算游离葡萄糖。通过离心法(10min,3000xg)将湿的菌丝体从液体中分离,并用2升丙酮萃取。丙酮真空蒸发(40℃)。残留的含水残渣用水稀释至500ml并用等量的乙酸乙酯萃取3次。合并有机相并用硫酸钠干燥,真空蒸发(40℃)得到830mg粗提物,随后进行制备性HPLC,如下所述(分离)。
将培养液加到含有500ml Bayer Lewapol CA 9225树脂的吸附柱上,并用1升水冲洗。吸附柱用1.5升4∶1的丙酮∶甲醇进行洗脱。溶剂真空蒸发(40℃)。残留的含水残渣用水稀释至500ml并用等量的乙酸乙酯萃取三次。合并有机相,并用硫酸钠干燥,真空蒸发(40℃)得到650mg粗提物,然后进行制备性HPLC,如下所述(分离)。
3:30L规模下JS360菌株的发酵(搅拌发酵罐)
含有30升Q6培养基的40升Biostat P发酵罐(BraunBioengeneering,Melsungen,德国)原位灭菌(121℃、1.1巴下进行1h)并用已繁殖76h的、两份生长良好的150ml YMG种子培养物接种。生产培养物在搅拌(240rpm)和通气(0.3vvm)条件下生长。测定pH,并使用拜尔Diastix Harnzuckerstreifen估算游离葡萄糖。此外,发酵罐装有Braun氧电极以测定培养液的氧饱和度。对由在无菌条件取样并用等量的乙酸乙酯萃取过的50ml样品制备的粗提物进行HPLC分析,由此作为实施例1的检测手段。实施例2和3也在发酵过程中采用HPLC-MS进行检测但无法在原粗提物中进行估算,因为在所采用的HPLC系统中在相似的保留时间下,量有限并且会与其他代谢物共洗出。乙酸乙酯萃取液用硫酸钠干燥,蒸发至干,再溶解在甲醇中并使用在总的实验方法部分所述的HPLC-UV系统进行分析。当从氧饱和度值推算培养物已完全饱和时,pH降至约4.5。培养基中的游离葡萄糖消耗完后,在发酵约60h时,开始采用HPLC分析方法估算实施例1的产量,它在114h后达到最大。然后,收获培养物,因为此后观察到实施例1产量的降低。收获培养物后,通过离心(10min,3000xg)将培养液与菌丝体分离并将其加到填充有Bayer Lewapol CA 9225吸附树脂的柱上,并用5升水冲洗。此后,柱用6升4∶1的丙酮∶甲醇洗脱。洗出液真空蒸发(40℃)至得到含水残渣,用水将含水残渣稀释至1升,并用1升乙酸乙酯萃取三次。合并有机相,用硫酸钠干燥并真空蒸发(40℃)。得到的提取物(22.7g)随后进行制备性HPLC,如下所述(分离)。
菌丝体用丙酮萃取三次,每次5升,并且使丙酮真空蒸发(40℃)得到含水残渣,用水将含水残渣稀释至1升并用1升乙酸乙酯萃取三次。合并有机相,用硫酸钠干燥并真空蒸发(40℃)。得到的提取物(13.4g)随后进行制备性HPLC,如下所述(分离)。
4.其他培养基中的发酵(烧瓶规模)
将JS360菌株在各种其他培养基中繁殖以优化实施例1及化学相关代谢物的产量。为此,以类似于Q6培养基中所述的一种方式(参见上述2)进行摇瓶发酵(shakeflask fermentation)。这样将含有150ml培养基的1升锥形瓶在28℃、240rpm的旋转振荡器上繁殖至多118小时。在发酵过程中,每天取样。测定pH,使用拜尔DiastixHarnzuckerstreifen估算游离葡萄糖。培养液的等分试样(50ml)用乙酸乙酯萃取。这些乙酸乙酯萃取液用硫酸钠干燥,蒸发至干,再溶解在甲醇中并使用总的实验方法部分所述的HPLC-UV和HPLC-MS系统进行分析。发酵72-96小时后通过比较保留时间和光谱,在以下培养基中检测实施例1化合物和相关化合物:YM培养基、C培养基、GS培养基、MC培养基、MCPM培养基、MS培养基以及SP培养基。然而,却在Q6培养基和GS培养基中观察到实施例1的最高产量。
实施例1
(1R,4R,5S)-1-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
制备参见下述。
实施例2
(1R,4R,5S)-1-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-[1-羟基-己基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
制备参见下述。
实施例3
(1R,4R,5S)-1-[(1R)-2-环己烯-1-基甲基]-4-己基-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
制备参见下述。
实施例4
(3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-3-羟基-4-[1-羟基-己基]-3-甲基-5-氧代-D-脯氨酸
制备参见下述。
实施例5
N-乙酰基-S-({(2R,3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-3-羟基-3-甲基-5-氧代-2-吡咯烷基}羰基)半胱氨酸
制备参见下述。
实施例6
N-乙酰基-S-({(2R,3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-4-己基-3-羟基-3-甲基-5-氧代-2-吡咯烷基}羰基)半胱氨酸甲酯
制备参见下述。
实施例7
(3S,4R)-2-[(S)-(1S)-2-环己烯-1-基(羟基)甲基]-3-羟基-4-己基-3-甲基-5-氧代-D-脯氨酸
绘制出的、由X射线分析测定的实施例2至7的立体化学结构与实施例1的结构类似。
实施例1至7的分离
1.摇瓶发酵得到的物质
将粗提物(分别来自菌丝体的620mg和来自培养液的830mg)溶解在5ml甲醇中,通过Bond Elut C18 500mg固相萃取柱柱体(Baker,Deventer,荷兰)过滤,并加到MZ Analysentechnik(Mainz,德国)Kromasil RP18柱(粒径,7μm;250×40mm)上。采用流速为10ml/min的0.01%TFA:乙腈作为流动相,t=0min时梯度为20%乙腈;40min内梯度从20%乙腈线性变化为50%乙腈;其后20min内梯度从50%乙腈线性变化为100%乙腈;接着保持75%乙腈30min,然后使柱再生。在210nm使用UV吸附合并馏分。实施例1在80-83min的保留时间(Rt)下洗脱,并且从菌丝体提取物和培养液提取物中分别得到14mg和1.5mg化合物。实施例2至5以及7得到微量的中间馏分,并且未从该提取物中分离得到纯品,而实施例6根本未检测到。
2:30L规模发酵得到的物质
将2.5-3克按照上述制备的粗提物(来自菌丝体的13.4g和来自培养液的22.7g)的等分试样溶解在5ml甲醇中,通过Bond Elut C18500mg固相萃取柱柱体(Baker,Deventer,荷兰)过滤,并加到MZAnalysentechnik(Mainz,德国)Kromasil RP18柱(粒径,7μm;250×40mm;0.01%TFA:乙腈作为流动相)上。采用流速为10ml/min的0.01%TFA:乙腈作为流动相,t=0min时梯度为20%乙腈;40min内梯度从20%乙腈线性变化为50%乙腈;其后20min内梯度从50%乙腈线性变化为100%乙腈;接着保持75%乙腈30min,然后使柱再生。在210nm使用UV吸附合并馏分。由此得到5种生物活性中间产物。观察到的它们在该梯度系统中的保留时间(Rt)如下:中间产物1(含实施例4和7)为61-64min,中间产物2(含实施例5和6)为65-71min,中间产物3(含实施例2)为72-79min,中间产物4(含实施例1)为79-85min,中间产物5(含实施例3)为86-93min。
中间产物1至5中活性组分的最终纯化通过制备性反相HPLC获得,该制备性反相HPLC使用的流速为7ml/min,固定相为MZAnalysentechnik Inertsil C18柱(7μm;250×30mm)以及如下梯度。t=0min=>t=30min保持条件恒定;之后50min内线性梯度从30%乙腈=>100%乙腈;接着保持条件恒定(100%乙腈)20分钟;然后使柱再生。实施例1至6的产量和Rt汇总于表1。
表1
实施例 | 产量(培养液提取物) | 产量(菌丝体提取物) | Rt(min) |
1 | 14mg | 160mg | 59-65 |
2 | 29mg | 43mg | 33-35 |
3 | 5mg | 18mg | 77-80 |
4 | 12mg | 17mg | 51-54 |
5 | 2mg | 14mg | 69-71 |
6 | (未分离) | 2mg | 72-73 |
7 | 19mg | (未分离) | 55-58 |
实施例1至7的表征
实施例1至6采用总的实验方法部分所描述的方法通过HPLC-UV和HPLC-MS进行检测。它们在HPLC分析系统中的特征汇总于表2。虽然实施例1、2、4和7给出了有关其分子峰的确定结果,但实施例3的LC-MS仅在正ESI模式下显示出分子峰,而由于负ESI模式下二氧化碳的损失,观察到较小的主要质量碎片峰。在实施例5和6中,在所采用的HPLC-MS条件下易于形成二聚物,因此主要的LC-MS信号与这些二聚物相关,而分子峰仅构成小的信号。通过对在萃取、下游处理和色谱法中获得的发酵液和中间馏分进行HPLC分析,这些特征还可用于识别各实施例化合物。
表2
实施例 | Rt(HPLC-UV-Vis)[min] | Rt(HPLC-MS)[min] | 分子峰m/z(正ESI) | 分子峰m/z(负ESI) |
1 | 8.95-8.97 | 6.39-6.43 | 336(M+H)+ | 334(M-H)- |
2 | 7.75-7.85 | 5.73-5.81 | 352(M+H)+ | 350(M-H)- |
3 | 9.74-9.76 | 6.86-6.90 | 320(M+H)+ | 276(M-CO2-H)+ |
4 | 6.85-6.87 | 5.28-5.30 | 368(M+H)+ | 370(M-H)- |
5 | 7.41-7.43 | 5.61-5.63 | 499(M+H)+;997(2M+H)+ | 497(M-H)-;995(2M-H)- |
6 | 8.00-8.05 | 5.81-5.84 | 513(M+H)+;1025(2M+H)+ | 511(M-H)- |
7 | 7.48-7.51 | 5.57-5.61 | 354(M+H) | 352(M-H)- |
实施例1至7的结构由低分辨和高分辨LC-MS光谱以及一维和二维NMR(核磁共振)光谱测定。关于仪器参数参见总的实验方法部分。
NMR数据表明环己基环中存在顺式双键。对HSQC、HMBC和COSY/TOCSY数据的周密分析使得能够确认双环结构,该双环结构与环己烯基甲醇部分均与在Salinosporamide A中发现的相同。HSQC数据指出在各分子中存在至少两个甲基。结合TOCSY和HMBC,识别出不带支链的己基部分。COSY谱图中明显的交叉峰(crosspeak)指出该链位于杂环体系中的2位。NMR和MS数据表明实施例7(与实施例1相比)以及实施例4(与实施例2相比)构成各自闭联形式(seco-form)的对应的β-内酯分子。由于峰的分裂以及特征性碳和质子化学位移,使12位(实施例2和4)上附加羟基的存在(与Salinosporamide A相比)变得明显。
实施例5和6的NMR光谱示出了一小组(subset)全新的、属于N-酰化半胱氨酸部分的信号。N-乙酰基-半胱氨酸分别通过前述β内酯环的羰基或在实施例7中的羧基与杂环结构连接。硫代酸酯键通过其羰基的化学位移(>200ppm)以及由HMBC推导出的与半胱氨酸β氢的连接而得以识别。半胱氨酸残基中的所有连接均通过HMBC和COSY光谱中对应信号的归属而得以确定。因此,实施例5和6的结构类似于乳胞素(lactacystin)。
光谱数据
实施例1
1H-NMR(500MHz,DMSO-d6):δ=0.87(t),1.28(m),1.29(m),1.23(m),1.40(m),1.45(m),1.47(m),1.54(m),1.58(m),1.68(m),1.74(s),1.80(m),1.90(m),2.29(m),2.41(t),3.65(m),5.47(m),5.73(m),5.81(m),8.92(s).
13C-NMR(DMSO-d6):δ=13.8,21.7,21.8,24.2,25.2,26.1,26.8,28.5,30.8,37.3,47.5,69.3,78.4,86.4,127.8,128.6,169.1,174.1.
实施例2
1H-NMR(500MHz,DMSO-d6):δ=0.88(t),1.27(m),1.29(m),1.35(s),1.37(m),1.49(m),1.58(m),1.59(m),1.71(m),1.75(m),1.93(m),2.35(d),2.76(m),3.49(m),4.00(d),4.68(m),5.70(m),5.91(m),6.11(br.),8.52(s).
13C-NMR(DMSO-d6):δ=13.4,21.0,21.4,23.7,24.2,29.6,30.1,31.5,36.1,54.6,69.4,75.0,76.0,76.5,127.9,170.9,172.3.
实施例3
1H-NMR(500MHz,DMSO-d6):δ=0.88(t)1.27(m),1.30(m),1.31(m),1.33(m),1.46(m),1.48(m),1.50(m),1.61(s),1.62(m),1.63(m),1.76(m),1.92(m),2.27(m),2.55(t),5.45(m);5.68(m),8.98(s).
13C-NMR(DMSO-d6):δ=13.3,19.6,21.4,24.0,24.2,26.5,28.2,28.5,29.9,30.9,32.5,46.7,74.0,86.1,127.7,130.9,170.4,170.8.
实施例4
1H-NMR(500MHz,DMSO-d6):δ=0.82(m),1.17(m),1.20(m),1.24(m),1.32(m),1.47(m),1.60(m),1.62(m),1.63(m),1.84(m),2.08(m)2.44(d),3.68(m),3.80(m),5.60(m),5.76(m).
13C-NMR(DMSO-d6):δ=13.1,20.1,20.6,21.0,23.5,23.6,30.5,33.5,37.7,52.7,67.1,73.6,75.2,80.1,126.3,128.6,171.2,176.5.
实施例5
1H-NMR(500MHz,DMSO-d6):δ=0.87(m),1.09(m),1.24(m),1.25(m),1.27(m),1.33(m),1.35(m),1.37(m),1.44(m),1.46(m),1.50(m),1.61(m),1.64(m),1.84(s),1.87(m),2.13(m),2.47(t),2.96(m),3.30(m),3.78(m),4.36(m),5.64(m),5.79(m).
13C-NMR(DMSO-d6):δ=13.9,20.8,21.7,22.0,22.1,22.2,23.4,24.3,26.8,27.7,28.7,29.2,31.1,38.1,50.3,51.0,75.3,79.7,80.6,127.0,129.3,169.3,178.9,201.2.
实施例6
1H-NMR(500MHz,DMSO-d6):δ=0.87(m),1.09(m),1.24(m),1.25(m),1.27(m),1.33(m),1.35(m),1.37(m),1.44(m),1.46(m),1.50(m),1.61(m),1.64(m),1.84(s),1.87(m),2.13(m),2.47(t),3.00(m),3.24(m),3.64(s),3.78(m),4.39(m),5.64(m),5.79(m).
13C-NMR(DMSO-d6):δ=13.6,20.8,21.7,22.0,22.1,23.4,24.3,26.8,27.7,28.7,29.3,31.1,38.1,50.3,51.4,51.8,75.3,79.7,80.6,127.0,129.3,169.3,171.0,178.9,201.2.
实施例7
1H-NMR(500MHz,DMSO-d6):δ=0.86(t),1.25(m),1.26(m),1.33(m),1.34(m),1.36(m),1.44(m),1.46(s),1.51(m),1.66(m),1.67(m),1.88(m),2.12(m),2.45(t),3.77(d),5.64(m),5.82(m),7.66(s).
13C-NMR(DMSO-d6):δ=13.8,20.3,21.5,21.7,23.3,24.4,26.5,27.9,28.9,31.0,38.5,50.5,74.6,75.5,80.4,127.4,129.7,177.5.
对NMR峰列表的解释:
实施例1:R1=H、R2=OH,实施例2:R1=OH、R2=OH,实施例3:R1=H、R2=H,
实施例4、实施例5:R8=H,实施例6:R8=CH3,实施例7(立体化学结构未通过NMR测出)。
实施例4 实施例5和6 实施例7
表3a
实施例1至3的化学位移在302K下、DMSO-d6中以500MHz测量。
碳 | 实施例1 | 实施例2 | 实施例3 |
C-1 | 174.1 | 172.3 | 170.8 |
C-2 | 47.5 | 54.6 | 46.7 |
C-3 | 86.4 | 76.0++ | 86.1 |
C-4 | 78.4 | 69.4++ | 74.0 |
C-5 | 69.3 | 75.0 | 32.5 |
C-6 | 37.3 | 36.1 | 29.9 |
C-7 | 128.6 | 127.9 | 130.9 |
C-8 | 127.8 | 127.9 | 127.7 |
C-9 | 25.2 | 24.2 | 24.0 |
C-10 | 21.7 | 21.0 | 19.6 |
C-11 | 26.1 | 29.6 | 28.2 |
C-12 | 24.2 | 76.5 | 24.2 |
C-13 | 26.8 | 31.5 | 26.5 |
C-14 | 28.5 | 23.7 | 28.5 |
C-15 | 30.8 | 30.1 | 30.9 |
C-16 | 21.8 | 21.4 | 21.4 |
C-17 | 13.8 | 13.4 | 13.3 |
C-18 | 21.8 | 21.4 | 21.4 |
C-19 | 169.1 | 170.9 | 170.4 |
++这些共振峰的归属可相互交换
表3b
实施例4至6的化学位移在302K下、DMSO-d6中以500MHz测量。
碳 | 实施例4 | 实施例5 | 实施例6 |
C-1 | 176.5 | 178.9 | 178.9 |
C-2 | 52.7 | 50.3 | 50.3 |
C-3 | 80.1 | 80.6 | 80.6 |
C-4 | 75.2 | 79.7 | 79.7 |
C-5 | 73.6 | 75.3 | 75.3 |
C-6 | 37.7 | 38.1 | 38.1 |
C-7 | 128.6 | 129.3 | 129.3 |
C-8 | 126.3 | 127.0 | 127.0 |
C-9 | 23.5 | 24.3 | 24.3 |
C-10 | 20.6 | 21.7 | 21.7 |
C-11 | 23.6 | 26.8 | 26.8 |
C-12 | 67.1 | 23.4 | 23.4 |
C-13 | 33.5 | 27.7 | 27.7 |
C-14 | 23.6 | 28.7 | 28.7 |
C-15 | 30.5 | 31.1 | 31.1 |
C-16 | 21.0 | 22.0 | 22.0 |
C-17 | 13.1 | 13.9 | 13.6 |
C-18 | 20.1 | 20.8 | 20.8 |
C-19 | 171.2 | 201.2 | 201.2 |
C-20 | - | 29.2 | 29.3 |
C-21 | - | 51.0 | 51.4 |
C-22 | - | 169.3 | 171.0 |
C-23 | - | 22.2 | 169.3 |
C-24 | - | 22.1 | 22.1 |
C-25 | - | - | 51.8 |
表3c
实施例7的化学位移在302K下、DMSO-d6中以500MHz测量。
碳 | 实施例7 |
C-1 | 50.5 |
C-2 | 177.5 |
C-3 | 75.5 |
C-4 | 80.4 |
C-5 | 20.3 |
C-6 | - |
C-7 | 74.6 |
C-8 | 38.5 |
C-9 | 129.7 |
C-10 | 127.4 |
C-11 | 24.4 |
C-12 | 21.5 |
C-13 | 26.5 |
C-14 | 23.3 |
C-15 | 27.9 |
C-16 | 28.9 |
C-17 | 31.0 |
C-18 | 21.7 |
C-19 | 13.8 |
表4a
实施例1至3的化学位移在302K下、DMSO-d6中以500MHz测量。
质子 | 实施例1 | 实施例2 | 实施例3 |
H-1 | - | - | - |
H-2 | 2.41t | 2.35d | 2.55t |
质子 | 实施例1 | 实施例2 | 实施例3 |
H-3 | - | - | - |
H-4 | - | - | - |
H-5 | 3.65m | 3.49m | 1.76m |
H-6 | 2.29m | 2.76m | 2.27m |
H-7 | 5.81m | 5.91m | 5.45m |
H-8 | 5.73m | 5.70m | 5.68m |
H-9 | 1.90,1.90m | 1.93,1.93m | 1.92,1.92m |
H-10 | 1.40,1.68m | 1.75,1.49m | 1.46,1.63m |
H-11 | 1.23,1.80m | 1.59,1.71m | 1.33,1.33m |
H-12 | 1.47,1.58m | 4.68m | 1.62,1.50m |
H-13 | 1.45,1.54m | 1.58,1.58m | 1.48,1.48m |
H-14 | 1.29,1.29m | 1.37,1.37m | 1.31,1.31m |
H-15 | 1.28,1.28m | 1.27,1.27m | 1.27,1.27m |
H-16 | 1.28,1.28m | 1.29,1.29m | 1.30,1.30m |
H-17 | 0.87t | 0.88t | 0.88t |
H-18 | 1.74s | 1.35s | 1.61s |
H-19 | - | - | - |
H N | 8.92s | 8.52s | 8.98s |
H-O-C-5 | 5.47 | 4.00d | - |
H-O-C-12 | - | 6.11(tent.) | - |
表4b
实施例4至6的化学位移在302K下、DMSO-d6中以500MHz测量。
质子 | 实施例4 | 实施例5 | 实施例6 |
H-1 | - | - | - |
H-2 | 2.44d | 2.47t | 2.47t |
H-3 | - | - | - |
H-4 | - | - | - |
H-5 | 3.68m | 3.78m | 3.78m |
H-6 | 2.08m | 2.13m | 2.13m |
H-7 | 5.76m | 5.79m | 5.79m |
H-8 | 5.60m | 5.64m | 5.64m |
质子 | 实施例4 | 实施例5 | 实施例6 |
H-9 | 1.84m | 1.87m | 1.87m |
H-10 | 1.62,1.32m | 1.61,1.33m | 1.61,1.33m |
H-11 | 1.63,1.17m | 1.64,1.09m | 1.64,1.09m |
H-12 | 3.80m | 1.46,1.37m | 1.46,1.37m |
H-13 | 1.60m | 1.50,1.35m | 1.50,1.35m |
H-14 | 1.32,1.20m | 1.24m | 1.24m |
H-15 | 1.20m | 1.25m | 1.25m |
H-16 | 1.24m | 1.27m | 1.27m |
H-17 | 0.82 | 0.87 | 0.87 |
H-18 | 1.47 | 1.44 | 1.44 |
H-19 | - | - | - |
H-20 | - | 3.30,2.96m | 3.24,3.00m |
H-21 | - | 4.36m | 4.39m |
H-22 | - | - | - |
H-23 | - | - | - |
H-24 | - | 1.84s | 1.84s |
H-25 | - | - | 3.64s |
表4c
实施例7的化学位移在302K下、DMSO-d6中以500MHz测量。
质子 | 实施例7 |
H-1 | 2.45t |
H-5 | 1.46s |
H-7 | 3.77d |
H-8 | 2.12m |
H-9 | 5.82m |
H-10 | 5.64m |
H-11 | 1.88,1.88m |
H-12 | 1.36,1.66m |
H-13 | 1.67,1.25m |
H-14 | 1.34,1.44m |
H-15 | 1.33,1.51m |
H-16 | 1.25m |
H-17 | 1.25m |
H-18 | 1.26m |
H-19 | 0.86t |
N-H | 7.66s |
高分辨质谱
实施例1:ESI-;质量实测值:334.1977,计算值:334.2014(对于分子式C19H28NO4,相当于4.1mDa的偏差)
实施例2:ESI-;质量实测值:350.1968,计算值:350.1967(对于分子式C19H28NO5,相当于0.1mDa的偏差)
实施例3:ESI+;质量实测值:276.2388,计算值:276.2327(对于分子式C18H30NO,相当于6.1mDa的偏差)。在该实施例中,在所述ESI条件下,仅能观察到(M-CO2)碎片。
实施例4:ESI+;质量实测值:368.2107,计算值:368.2073(对于分子式C19H31NO6,相当于3.3mDa的偏差)
实施例5:ESI-;质量实测值:497.2322,计算值:497.2321(对于分子式C24H38N2O7S,相当于0.0mDa的偏差)
实施例6:ESI-;质量实测值:511.2594,计算值:511.2478(对于分子式C25H40N2O7S,相当于11.6mDa的偏差)
实施例7:ESI+;质量实测值:354.2268,计算值:354.2280(对于分子式C19H32NO5,相当于1.3mDa的偏差)
按照方法B合成本发明化合物的实施例
通过文献(J.AM.Chem.Soc.1999,121,9967-9976)中所述的方法合成5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯。
4-[2-羟基-3-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯
将2.00g(8.10mmol)5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯的无水THF(45ml)溶液加入16.2ml、-80℃的LHMDS(THF中,1M,16.2mmol)中。60分钟后,将32.4ml氯化二甲基铝(己烷中,1M)在45分钟内逐滴加入并在-80℃下继续搅拌90分钟。在15分钟内加入4.86g(24.3mmol)2-乙酰基辛酸甲酯的10ml THF溶液。然后将反应混合物温热至-20℃并继续搅拌60分钟。重新冷却到-75℃后,加入20ml饱和氯化氨的水溶液。将混合物倒入100ml饱和的氯化铵水溶液、20ml 6N HCl和100ml乙酸乙酯中。水层用乙酸乙酯萃取,并且合并有机层,依次用100ml水、100ml饱和的NaHCO3水溶液和盐水洗涤,最后用NaSO4干燥。溶剂蒸发后,残渣用色谱法在二氧化硅(环己烷/乙酸乙酯)上纯化得到四种非对映异构体:
4-[2S-羟基-3S-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯:365mg,logP 5.93;
不可分离的4-[2S-羟基-3R-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯(MATA107-4-3)与4-[2R-羟基-3S-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯的混合物:560mg,logP 5.48和5.56;
4-[2R-羟基-3R-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯:520mg,logP 5.32。
4R-己基-3S-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯和4S-己基-3R-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯
将500mg不可分离的4-[2R-羟基-3R-(甲氧基羰基)-壬基]-5S-异丙基-2-苯基-4,5-二氢-1,3-噁唑-4R-羧酸甲酯的混合物与784mg 20%Pd(OH)2/C的6ml MeOH/AcOH(9∶1)的溶液在室温下于20巴氢气下搅拌72h。通过二氧化硅过滤后蒸发溶剂。残渣溶于20ml乙酸乙酯中,并依次用10ml饱和的4.5M K2CO3水溶液以及10ml盐水洗涤。有机层用NaSO4干燥并真空蒸发。粗产物通过色谱法在二氧化硅(环己烷/乙酸乙酯)上纯化得到4R-己基-3S-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯和4S-己基-3R-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯:(185mg,logP2.16和2.58)。
4R-己基-3S-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸和4S-己基-3R-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸
将180.0mg 4R-己基-3S-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯、4S-己基-3R-羟基-2R-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸甲酯和731mg LiI的无水吡啶(18mL)溶液加热至回流3小时。重新冷却后,真空蒸发溶剂。残渣溶于水(20mL)中并用乙酸乙酯(10mL)萃取。水层用0.5M HCl酸化至pH 2并用乙酸乙酯(3×15ml)萃取。有机层用盐水洗涤,NaSO4干燥并浓缩,得到90mg不可分离的异构体混合物(logP 1.86和1.98)。
实施例8和9(表1)
(1R,4R,5S)-4-己基-1-[(1S)-1-羟基-2-甲基丙基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮(MATA121-1)和(1R,4S,5S)-4-己基-1-[(1S)-1-羟基-2-甲基丙基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮
向含有60μl三乙胺的、90mg 4R-己基-3S-羟基-2-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸与4S-己基-3S-羟基-2-[1S-羟基-2-甲基丙基]-3-甲基-5-氧代吡咯烷-2-羧酸混合物的无水THF(4.5mL)的冷(<5℃)溶液中,逐滴加入氯甲酸异丙烯基酯(38mg)。反应混合物在<5℃下搅拌60min,并再在室温下搅拌60min。搅拌20min后加入乙酸乙酯(10mL)得到悬浮液,将该悬浮液过滤并蒸发。残渣通过色谱法在二氧化硅(环己烷/乙酸乙酯)上纯化,得到(1R,4R,5S)-4-己基-1-[(1S)-1-羟基-2-甲基丙基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮(12mg;logP 2,79)和(1R,4S,5S)-4-己基-1-[(1S)-1-羟基-2-甲基丙基]-5-甲基-6-氧杂-2-氮杂双环[3.2.0]庚-3,7-二酮(16mg;LogP 2,87)
按照方法F合成本发明化合物的实施例
2-(叔丁氧基羰基氨基)丙二酸二乙酯有市售或可通过对氨基丙二酸二乙酯盐酸盐进行常规的boc保护来合成。
1.2-苄基-2-(叔丁氧基羰基氨基)丙二酸二乙酯
将4.3g(190mmol)钠溶于600ml无水乙醇中并用47g(170mmol)2-(叔丁氧基羰基氨基)丙二酸二乙酯的200ml乙醇溶液缓慢处理。搅拌30min后,在室温下逐滴加入29.2g(170mmol)苄基溴。反应混合物回流12h然后加入HCl水溶液(pH 6-7),蒸发溶剂并随后用二氯甲烷/水萃取。合并的有机层用MgSO4干燥,蒸发溶剂得到产率为88%的纯产品(55g)。
1H-NMR{400MHz,DMSO-d6}:1.18(t,3JHH=7Hz,6H,CH3);1.42(s,9H,CH3);3.44(s,2H,CH2);4.18(m,4H,CH2);6.2(b,1H,NH);7.01(b,2H,Ph-H);7.26(b,3H,Ph-H).
LC:87%纯度,MS:266(M-boc)
2.苄基[[3-苄氧基-3-氧代丙酰基](叔丁氧基羰基)氨基]丙二酸二乙酯
在室温下,将28.2g(77mmol)2-苄基-2-(叔丁氧基羰基氨基)丙二酸二乙酯、15g(77mmol)丙二酸单苄酯和12.5g(97mmol)N,N-二异丙基乙胺溶于300ml二氯甲烷中并用14.8g(77mmol)1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐处理。反应混合物搅拌12h,用乙酸乙酯稀释,用1N HCl水溶液(200ml)和NaHCO3水溶液(2×200ml)洗涤并用MgSO4干燥。溶剂蒸发后,得到产率78%的产品(32.5g)。
1H-NMR{400MHz,DMSO-d6}:1.18(t,3JHH=7Hz,6H,CH3);1.43(s,9H,CH3);3.64(s,2H,CH2);4.17(m,4H,CH2);5.15(s,2H,CH2);7.00(b,2H,Ph-H);7.26(b,3H,Ph-H);7.35(b,5H,Ph-H).
3.4-苄基-1-叔丁基-2-乙基-2-苄基-3,5-二氧代吡咯烷-1,2,4-三羧酸酯
在室温下,将6.0g(11mmol)苄基[[3-苄氧基-3-氧代丙酰基](叔丁氧基羰基)-氨基]丙二酸二乙酯溶于100ml二甲基甲酰胺中,并用3.1g(27mmol)叔丁醇钠处理。反应混合物在50℃搅拌12h,用二氯甲烷稀释,用1N HCl水溶液调至中性,用水(1×50ml)和NaHCO3(1×500ml)水溶液洗涤,并用MgSO4干燥。溶剂蒸发后,得到油状粗产品,将该粗产品用色谱法(环己烷∶乙酸乙酯为1∶1)纯化得到2.6g(47%)非对映异构体混合物形式的产品。
1H-NMR{400MHz,DMSO-d6}:1.13和1.18(t,3H,3JHH=7Hz,CH3);1.39和1.43(s,9H,CH3);3.46和3.64(s,2H,CH2);4.15(m,2H,CH2);5.15(s,2H,CH2);7.03(b,2H,Ph-H);7.26(b,3H,Ph-H);7.35(b,5H,Ph-H).
4.4-苄基-1-叔丁基-2-乙基-2-苄基-4-[(2-E)-己-2-烯-1-基]-3,5-二氧代吡咯烷-1,2,4-三羧酸酯
将0.4g(0.8mmol)4-苄基-1-叔丁基-2-乙基-2-苄基-3,5-二氧代吡咯烷-1,2,4-三羧酸酯、0.2g(1.9mmol)反-2-己烯-1-醇、0.1g(0.9mmol)三乙胺、18mg(0.08mmol)乙酸钯、40mg(0.16mmol)三苯基膦和80mg(0.8mmol)三乙基甲硼烷在20ml THF中搅拌4h。反应混合物用乙酸乙酯稀释,用1N HCl水溶液(1×20ml)、水(2×20ml)和NaHCO3水溶液(1×20ml)洗涤并用MgSO4干燥。溶剂蒸发后,得到非对映异构体混合物形式的粗产品(0.43g,92%)。
1H-NMR{400MHz,DMSO-d6}:0.88(t,3H,3JHH=7Hz,CH3);1.13和1.18(t,3H,3JHH=7Hz,CH3);1.20-1.35(m,4H,CH2);1.39和1.42(s,9H,CH3);1.90(m,2H,CH2);3.46和3.64(s,2H,CH2);4.15(m,2H,CH2);5.14(s,2H,CH2);5.54(m,2H,CH);7.02(b,2H,Ph-H);7.25(b,3H,Ph-H);7.33(b,5H,Ph-H).
5.4-苄基-1-叔丁基-2-乙基-2-苄基-4-[(2-E)-己-2-烯-1-基]-3-羟基-5-氧代吡咯烷-1,2,4-三羧酸酯(实例462)
在室温下,将2.1g(3.6mmol)4-苄基-1-叔丁基-2-乙基-2-苄基-4-[(2-E)-己-2-烯-1-基]-3,5-二氧代吡咯烷-1,2,4-三羧酸酯和770mg(3.6mmol)NaBH(OAc)3在40ml冰醋酸中搅拌36h。反应混合物用水稀释并用二氯甲烷萃取。合并的有机层用水(2×20ml)和NaHCO3水溶液(1×20ml)洗涤并用MgSO4干燥。溶剂蒸发后,得到非对映异构体混合物形式的粗产品(1.25g,60%)。
1H-NMR{400MHz,DMSO-d6}:0.89(t,3H,3JHH=7Hz,CH3);1.14和1.18(t,3H,3JHH=7Hz,CH3);1.20-1.35(m,4H,CH2);1.39和1.42(s,9H,CH3);1.90(m,2H,CH2);3.42,3.46和3.64(s,2H,CH2);4.15(m,2H,CH2);5.14(s,2H,CH2);5.54(m,2H,CH);7.02(b,2H,Ph-H);7.25(b,3H,Ph-H);7.33(b,5H,Ph-H),OH未检测到。
MS:480(M-boc)
根据前述方法,可以得到或已经得到在下表中列举的式(Ia)增环内酰胺(annelated lactame):
表5
LogP值的测定按照EEC-Directive 79/831.Annex V.A8通过HPLC进行(梯度法,乙腈/0.1%磷酸水溶液)。
根据前述方法,可以得到或已经得到在下表中列举的式(I)内酰胺:
表6
LogP值的测定按照EEC-Directive 79/831.Annex V.A8通过HPLC进行(梯度法,乙腈/0.1%磷酸水溶液)。
chiral=手性
*BnOCO=苄氧基羰基
**BOC=叔丁氧基羰基
B.生物试验实施例
实施例1
叉丝单囊壳属试验(苹果)/保护性
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
通过将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度,制得合适的活性化合物制剂。
为测试保护活性,用活性化合物的制剂以所述的施用率喷洒植物幼苗。当喷涂层变干后,用苹果霉病(白叉丝单囊壳(Podosphaeraleucotricha))的病原剂的孢子水性悬浮液接种该植株。然后将植株置于温度为约23℃,相对大气湿度为约70%的温室中。
接种后7天进行评估。0%表示药效等于对照组的药效,而100%的药效表示完全未观察到病害。
实施例1的化合物在100g/ha的施用率下表现出100%药效。
实施例2
黑星菌属试验(苹果)/保护性
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
通过将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度,制得合适的活性化合物制剂。
为测试保护活性,用活性化合物的制剂以所述的施用率喷洒植物幼苗。当喷涂层变干后,用苹果黑星病的病原剂(苹果黑星病菌(Venturia inaequalis))的分生孢子水性悬浮液接种该植株,然后将植株置于温度为约20℃,相对大气湿度为100%的培养室中1天。
再将植物置于温度为约21℃,相对大气湿度为约90%的温室中。
接种后10天进行评估。0%表示药效等于对照组的药效,而100%的药效表示完全未观察到病害。
实施例1的化合物在100g/ha的施用率下表现出100%药效。
实施例3
灰葡萄孢试验(豆)/保护性
溶剂:24.5重量份丙酮
24.5重量份二甲基乙酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
通过将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度,制得合适的活性化合物制剂。
为测试保护活性,用活性化合物的制剂喷洒植物幼苗。当喷涂层变干后,用两小块长有灰葡萄孢(Botrytis cinerea)的琼脂放在各片叶子上。将接种后的植株置于温度为约20℃、相对大气湿度为100%的暗室中。
接种后2天,对叶子的病灶(lesion)大小进行评估。0%表示药效等于对照组的药效,而100%的药效表示完全未观察到病害。
实施例1的化合物在500g/ha的施用率下表现出90%药效。
实施例4
单囊壳属试验(黄瓜)
溶剂:49重量份N,N-二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
通过将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度,制得合适的活性化合物制剂。
为测试保护活性,用活性化合物的制剂以所述的施用率喷洒植物幼苗。处理后一天,用凤仙花单囊壳(Sphaerotheca fuliginea)的病原剂的孢子水性悬浮液接种该植株。然后将植株置于温度为约23℃,相对大气湿度为约70%的温室中。
接种后7天进行评估。0%表示药效等于对照组的药效,而100%的药效表示完全未观察到病害。
实施例1、8和10的化合物在500ppm的施用率下表现出70%药效。
实施例5
用致病疫霉作为供试微生物计算ED50值的离体试验
将10μl供试化合物的甲醇溶液与乳化剂烷基芳基聚乙二醇醚一起加入到96孔微量滴定板的各孔中。其后,使溶剂在通风橱中挥发。接着,向各孔中加入200μl、已添加有合适浓度的致病疫霉(Phytophthora infestans)孢子或菌丝体悬浮液的马铃薯葡萄糖培养液。
在各微量滴定孔中得到的供试化合物的浓度为50、5、0.5和0.05ppm。在所有微孔中得到的乳化剂浓度恒定地为300ppm。
借助于光度计在620nm波长处测量所有孔中的消光情况。
然后将微量滴定板转移到振荡器上,在20℃、85%相对湿度下保持3-5天。
培育结束时,再在620nm波长处通过光度法测量供试生物的生长情况。两个消光值(培育前后)的差与供试微生物的生长成比例。
根据由不同测试浓度以及未处理的供试微生物(对照)得到的Δ消光数据算得剂量-应答曲线。将产生50%生长抑制所必须的浓度定义并称为ED50值(=引起50%生长抑制的有效剂量(EffectiveDose)),单位为ppm(=mg/l)。
实施例1、3和4的化合物表现出小于0.05的ED50值。
实施例6
草地贪夜蛾试验(敏感菌株)
方法:将1mg化合物溶于100μl丙酮中;用900μl、0.02%(w/v)Triton X-100的水溶液稀释。
将结球甘蓝(Brassica oleracea)叶片浸入所需浓度的活性化合物制剂中处理,在叶子仍然湿润时感染草地贪夜蛾(Spodopterafrugiperda)的幼虫。
六天后,确定百分死亡率。100%表示杀死所有蠋;0%表示无蠋被杀死。
在该试验中,例如实施例1的化合物表现出100%的药效。
Claims (10)
1.式(I)化合物或其盐用于防治植物致病微生物或有害动物的用途
其中各符号具有下述含义:
R1 相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、SO2NR2”、COOR”、COSR’、CSOR’、-O-COR”、-O-CSR’、-CO-R”或CONR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
n为0、1或2;
R2为氢、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、COOR”、CSOR”、COSR’、-CO-R”或者CONR2”;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C12)烯基、未取代或取代的(C3-C12)炔基、未取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、S(O)nR’、COOR’、CSOR’、COSR’、-CO-R’、CONR2”或者G;
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基、SO2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
或者
R5和R6一起形成键。
2.权利要求1的用途,其中式(I)中的各符号具有以下含义:
R1相同或不同,为氢、氯、溴、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、OR”、COOR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环或含有一个或两个杂原子单元的三至六元环;
R2为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、COOR”、-CO-R”或者CONR2”;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C10)烯基、未取代或取代的(C3-C10)炔基、SO2R’、COOR’、-COR’、CONR2”或者G;
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的苯基、未取代或取代的杂环基、SO2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
或者
R5和R6一起形成键,
R’相同或不同,为(C1-C10)烷基、(C2-C10)烯基、(C2-C10)炔基、(C3-C6)环烷基、(C3-C6)环烯基、苯基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
n为0、1或2。
3.权利要求1或2的用途,其中式(I)化合物为式(II)化合物,
其中各符号具有下述含义:
R1相同或不同,为氢、氯、溴、未取代或取代的(C1-C10)烷基、未取代或取代的(C2-C8)烯基、未取代或取代的(C2-C8)炔基、未取代或取代的苯基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、COOR”、OR”或-CO-R”,或者两个R1取代基一起形成三至六元碳环;
R2为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO 2R’、COOR’、-COR’、或者G;
R5为氢、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR’、CONR2”、未取代或取代的苯基、未取代或取代的杂环基、或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
或者
R5和R6一起形成键,
R7为氢、氟、氯、O-R”、SR”、NR”2、-O-COR’、-S-COR’、-O-CSR’、-O-SO2R’、-O-COOR’、-O-CSOR’、-O-CONR2”、NO2或CN;
R8为氢、未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的苯基、或者未取代或取代的杂环基;或者
R7和R8一起为=O或=S;
R9为氢、卤素、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C10)烯基、未取代或取代的(C2-C10)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R’或SR’;
或者
R8和R9一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
R’相同或不同,为(C1-C8)烷基、(C2-C6)烯基、(C2-C6)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R”;
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CH(CH3)2),SiEt2i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe);
n为0、1或2。
4.权利要求3的用途,其中式II中的符号具有如下含义:
R1相同或不同,为氢,氯,溴,(C1-C8)烷基,(C2-C6)烯基,(C2-C8)炔基,苯基,其中后四者基团为未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代,未取代的或被氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2或CN所取代的杂环基,未取代的或被选自氟、氯、甲基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的(C3-C6)环烷基或(C3-C8)环烯基,或者两个R1取代基一起形成三至六元碳环;
R2为氢,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的甲基、乙基、丙基、异丙基、烯丙基、炔丙基、环丙基、环丁基、环戊基、环己基、苯基,或未取代的或被选自氟、氯、甲基、乙基、三氟甲基、甲氧基、NO2和CN的一至三个取代基所取代的杂环基;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C3-C6)烯基、未取代或取代的(C3-C6)炔基、SO2R’、COOR’、-COR’、CONR2”、或者G;
R5为氢、(C1-C6)烷基、(C2-C6)烯基、(C2-C8)炔基、未取代或取代的(C3-C6)环烷基、SO2R’、COOR’、-COR’、CONR2”或者G;
R6为OR”、SR”或NR2”;
或者
R5和R6一起形成键,
R7为羟基、巯基、SCH3、氟、氯、溴、甲基、乙基、甲氧基、三氟甲氧基、乙氧基、-O-SO2R’、-O-COOR’、-O-CONR2”、CN、NR”或O-G;
R8为氢,未取代或取代的(C1-C4)烷基、未取代或取代的(C2-C4)烯基、未取代或取代的(C2-C4)炔基、未取代或取代的(C3-C6)环烷基、未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的苯基,未取代的或被选自氟、氯、甲基、乙基、异丙基、叔丁基、三氟甲基、三氟甲氧基、甲氧基、乙氧基、NO2和CN的一至三个取代基所取代的杂环基;
或者
R7和R8一起为=O或=S;
R9为氢、卤素、未取代或取代的(C1-C8)烷基、未取代或取代的(C2-C6)烯基、炔丙基、未取代或取代的(C6-C10)芳基、未取代或取代的杂环基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基;
或者特别优选
R8和R9一起形成三至六元碳环或含有一个或两个杂原子单元的三
至六元环;
G为SiMe3,SiEt3,SiMe2t-Bu,SiMe(t-Bu)2,Si-i-Pr3,Si-t-BuPh2,SiMePh2,SiPh3,SiMe2(C(CH3)2-CR(CH3)2),SiEt2 i-Pr,SiMe2i-Pr,SiMe2i-Bu,SiBz3,Si(CH2-C6H4-CH3)3,SiPh2(O-i-Pr),SiPh2(O-t-Bu),Sit-BuPh(OMe),或者SiMe2(O-C2H4-OMe).
R’相同或不同,为(C1-C6)烷基、(C2-C4)烯基、(C2-C4)炔基、(C3-C6)环烷基、苯基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’。
5.权利要求1至4中一项或多项的用途,其中式(I)化合物以与一种或多种其他农用化学活性化合物混合的形式使用。
6.权利要求1至5中一项或多项的用途,其中式(II)化合物以拌种剂的形式施用。
7.权利要求1至6中一项或多项的用途,其中向转基因植物作用施用式(II)化合物。
8.一种防治植物致病微生物和有害动物的方法,该方法包括向植物致病微生物或有害动物或其生境施用权利要求1的式(I)化合物。
9.一种式(Ia)化合物或其盐,
其中各符号具有下述含义:
R1相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、COOR”、CSOR’、COSR’、-O-COR’、-O-CSR’、-CO-R”、CONR2”、SO2NR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
n为0、1或2;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
R2为未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基或者未取代或取代的杂环基、COOR”、CSOR’、COSR’、-CO-R’或者CONR2”;
并且
R4为氢、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C6)环烯基、S(O)nR’、COOR’、CSOR’、COSR’、-CO-R’、CONR2”或者G;并且
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
条件是排除以下化合物:
10.一种式(Ib)化合物或其盐,
其中各符号具有下述含义:
R1相同或不同,为氢、卤素、未取代或取代的(C1-C20)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、O-R”、S(O)nR”、COOR”、CSOR’、COSR’、-O-COR’、-O-CSR’、-CO-R”或CONR2”,或者两个R1取代基一起形成三至八元碳环或含有一个或两个杂原子单元的三至八元环;
n为0、1或2;
R’相同或不同,为(C1-C12)烷基、(C2-C12)烯基、(C2-C12)炔基、(C3-C8)环烷基、(C3-C8)环烯基、(C6-C12)芳基或杂环基,所有这些基团均为未取代的或取代的;
R”相同或不同,为H或R’;
R2为未取代或取代的(C1-C5)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基、或者未取代或取代的杂环基;
R3为氢、未取代或取代的(C1-C6)烷基、未取代或取代的(C2-C6)烯基、未取代或取代的(C2-C6)炔基、未取代或取代的(C3-C6)环烷基、未取代或取代的(C3-C6)环烯基、未取代或取代的(C6-C12)芳基或未取代或取代的杂环基、CSOR’、COSR’、-CO-R”或者CONR2”;
R4为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C6)环烯基、S(O)nR’、COOR’、CSOR’、-CO-R’、CON’R2”或者G;
R5为氢、未取代或取代的(C1-C12)烷基、未取代或取代的(C2-C12)烯基、未取代或取代的(C2-C12)炔基、未取代或取代的(C3-C8)环烷基、未取代或取代的(C3-C8)环烯基、未取代或取代的(C6-C12)芳基、未取代或取代的杂环基、SO2R’、COR’、COOR’、COSR’、CSOR’、CONR2”或者G;
G为Si[(C1-C6)烷基]x[(CH2)t-苯基-(CH3)u]y[(O)v-((C1-C4)亚烷基)-(O-(C1-C4)亚烷基)w-H]z,
其中x、y、z为0、1、2或3并且x+y+z=3,t、u为0
或1,v、w为0或1并且v+w为1或2;
R6为OR”、SR”或NR2”;
排除其中
R1=H,R2=CH3,R3=H,R4=H,C6H5,CH2-C6H5,C2H5,R5=H且R6=NH2,NHC6H5,
NHCH2C6H5的化合物。
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CN107474004A (zh) * | 2016-06-07 | 2017-12-15 | 中国科学院上海有机化学研究所 | 三氟甲基季碳中心化合物及其制备方法和应用 |
TWI648001B (zh) * | 2013-08-16 | 2019-01-21 | 洛斯阿拉莫斯國家安全有限責任公司 | 用於改良植物性能之化合物及方法 |
CN112986460A (zh) * | 2021-04-15 | 2021-06-18 | 秦皇岛海关技术中心 | 植物源食品中双胍三辛烷基苯磺酸盐残留量的检测方法 |
CN115490606A (zh) * | 2022-09-30 | 2022-12-20 | 安徽泽升科技有限公司 | 一种由2-氯亚甲基-丙二酸二乙酯制备医药中间体的方法 |
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US7176232B2 (en) | 2002-06-24 | 2007-02-13 | The Regents Of The University Of California | Salinosporamides and methods for use thereof |
US7579371B2 (en) | 2004-04-30 | 2009-08-25 | Nereus Pharmaceuticals, Inc. | Methods of using [3.2.0] heterocyclic compounds and analogs thereof |
MXPA06012421A (es) | 2004-04-30 | 2007-01-31 | Nereus Pharmaceuticals Inc | Compuestos de heterociclicos y metodos para utilizar los mismos. |
DK1830838T3 (da) | 2004-12-03 | 2013-01-21 | Dana Farber Cancer Inst Inc | Sammensætninger og fremgangsmåder til behandling af neoplastiske sygdomme |
US7842814B2 (en) | 2006-04-06 | 2010-11-30 | Nereus Pharmaceuticals, Inc. | Total synthesis of salinosporamide A and analogs thereof |
WO2008095195A2 (en) | 2007-02-02 | 2008-08-07 | Nereus Pharmaceuticals, Inc. | Lyophilized formulations of salinosporamide a |
MX2010009860A (es) | 2008-03-07 | 2010-09-30 | Nereus Pharmaceuticals Inc | Sintesis total de salinosporamida a y sus analogos. |
KR20110011645A (ko) | 2008-05-12 | 2011-02-08 | 니리어스 파마슈티컬즈, 인코퍼레이션 | 프로테아좀 저해제로서의 살리노스포라마이드 유도체 |
TW201825458A (zh) | 2016-09-20 | 2018-07-16 | 英商葛蘭素史克智慧財產(第二)有限公司 | Trpv4拮抗劑 |
US11260049B2 (en) | 2016-09-20 | 2022-03-01 | Glaxosmithkline Intellectual Property (No. 2) Limited | TRPV4 antagonists |
WO2018055527A1 (en) | 2016-09-20 | 2018-03-29 | Glaxosmithkline Intellectual Property (No.2) Limited | Trpv4 antagonists |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714740D0 (en) * | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
CA3115351C (en) | 2018-12-04 | 2023-06-20 | Virox Technologies Inc. | An antimicrobial composition comprising an antimicrobial agent consisting of a c3-c5 n-alkyl-gamma-butyrolactam and uses thereof |
CN109851772B (zh) * | 2018-12-26 | 2021-07-30 | 温州大学 | 一种含羟基和活泼双键的多嵌段聚乙二醇及其制备方法 |
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BE891687A (fr) * | 1982-01-05 | 1982-04-30 | Richter Gedeon Vegyeszet | Composes heterocycliques contenant un groupe c-acetyle et leur procede de preparation |
JPH01277492A (ja) * | 1988-04-27 | 1989-11-07 | Sankyo Co Ltd | 新規抗生物質シネラゾール |
EP1597262B1 (en) * | 2003-02-14 | 2009-11-11 | InterMed Discovery GmbH | Substituted heterocycles |
AU2004253478A1 (en) * | 2003-06-20 | 2005-01-13 | Nereus Pharmaceuticals, Inc. | Use of [3.2.0] heterocyclic compounds and analogs thereof for the treatment of cancer, inflammation and infectious diseases |
-
2005
- 2005-07-09 US US11/572,086 patent/US20080064736A1/en not_active Abandoned
- 2005-07-09 KR KR1020077003084A patent/KR20070041742A/ko not_active Application Discontinuation
- 2005-07-09 CN CNA2005800302034A patent/CN101133022A/zh active Pending
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TWI648001B (zh) * | 2013-08-16 | 2019-01-21 | 洛斯阿拉莫斯國家安全有限責任公司 | 用於改良植物性能之化合物及方法 |
CN107474004A (zh) * | 2016-06-07 | 2017-12-15 | 中国科学院上海有机化学研究所 | 三氟甲基季碳中心化合物及其制备方法和应用 |
CN107474004B (zh) * | 2016-06-07 | 2022-07-19 | 中国科学院上海有机化学研究所 | 三氟甲基季碳中心化合物及其制备方法和应用 |
CN112986460A (zh) * | 2021-04-15 | 2021-06-18 | 秦皇岛海关技术中心 | 植物源食品中双胍三辛烷基苯磺酸盐残留量的检测方法 |
CN115490606A (zh) * | 2022-09-30 | 2022-12-20 | 安徽泽升科技有限公司 | 一种由2-氯亚甲基-丙二酸二乙酯制备医药中间体的方法 |
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CR8840A (es) | 2008-02-13 |
ECSP077159A (es) | 2007-02-28 |
BRPI0513262A (pt) | 2008-04-29 |
ZA200700278B (en) | 2007-11-28 |
JP2008505956A (ja) | 2008-02-28 |
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