CN1630634A - 光学活性的2,5-二芳基-△1-吡咯啉及其作为害虫防治剂的用途 - Google Patents
光学活性的2,5-二芳基-△1-吡咯啉及其作为害虫防治剂的用途 Download PDFInfo
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- CN1630634A CN1630634A CNA018191061A CN01819106A CN1630634A CN 1630634 A CN1630634 A CN 1630634A CN A018191061 A CNA018191061 A CN A018191061A CN 01819106 A CN01819106 A CN 01819106A CN 1630634 A CN1630634 A CN 1630634A
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- 238000000034 method Methods 0.000 claims abstract description 96
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- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 229940063650 terramycin Drugs 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 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
- 238000012546 transfer Methods 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- WVZPYZMQQDNINJ-UHFFFAOYSA-N tributyl(butylstannyloxy)stannane Chemical compound CCCC[SnH](CCCC)O[SnH](CCCC)CCCC WVZPYZMQQDNINJ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 241000701451 unidentified granulovirus Species 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000006200 vaporizer Substances 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229940100050 virazole Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 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
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
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- 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
- C07D207/20—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
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Abstract
本发明涉及式(I)的新的光学活性的Δ1-吡咯啉,其中R1、R2、R3、R4和m具有说明书中给出的含义,本发明还涉及制备这些物质的多种方法以及它们用于防治害虫的用途。
Description
本发明涉及新的光学活性的2,5-二芳基-Δ1-吡咯啉、其制备方法及其作为害虫防治剂的用途。
WO 00/21958、WO 99/59968、WO 99/59967和WO 98/22438已经描述了外消旋的Δ1-吡咯啉作为害虫防治剂。
但是这些已知的外消旋体的作用强度和/或作用持续时间并非在所有应用领域都完全令人满意,尤其是针对特定的生物体和/或在低用量的情况下。
然而,由于对现代害虫防治剂的各种要求,例如对作用强度、作用的持续时间、作用谱、应用谱、毒性、与其它活性物质的组合、与制剂助剂的组合或其合成所涉及到的,以及由于可能出现的抗性,对这类物质的开发从来不能认为是结束了,并且一直高度需求与已知化合物相比至少带来部分优点的新化合物。
本发明的目的是提供通式(I)的光学活性化合物,由此在用作害虫防治剂时可减少用量。
现已发现式(I)的新的光学活性的Δ1-吡咯啉
其中
*表示具有(R)构型的手性碳原子,
m表示0、1、2、3或4,
R1表示卤素或甲基,
R2表示氢或卤素,
R3表示氢、卤素、羟基、烷基、链烯基、炔基、卤代烷基、卤代链烯基、烷氧基、-S(O)oR6、-OSO2R6、二烷氧基甲硼烷、-B(OH)2或表示
任选被列于W1的基团一或多取代的苯基,
R4表示卤素、烷基、烷氧基、卤代烷基、卤代烷氧基或-S(O)oR6,
W1表示氰基、卤素、羟基、烷基、烷氧基、卤代烷基、卤代烷氧基、链烯基、卤代链烯基、链烯基氧基、卤代链烯基氧基、烷氧基羰基、三烷基甲硅烷基、三烷基甲硅烷基氧基、-CONH2、-NR7R8、-S(O)oR6或-SO2NR7R8,
o表示0、1或2,
R6表示氢、烷基或卤代烷基,
R7和R8各自独立表示氢、烷基、卤代烷基或一起表示亚烷基或烷氧基亚烷基。
在上述和下述的所有化合物中,结构式中带星号(*)的各表示(R)-构型的手性碳原子。
此外,已发现式(I)的光学活性化合物可如下得到
A)式(I-rac)的外消旋化合物
其中
R1、R2、R3、R4和m具有上述含义,
在手性硅胶固定相上,在洗脱剂或洗脱剂混合物作为液相存在下色谱分离,或
B)(i)式(I-a)化合物
其中R1、R2、R4和m具有上述含义,和
X1表示Cl、Br、I、-OSO2CF3、-OSO2(CF2)3CF3,与式(II)的金属有机化合物
A-M (II)
其中
A表示任选被列于W1的基团一或多取代的苯基,
其中W1具有上述含义,和
M表示-B(OH)2、Sn(nBu)3或ZnCl,
M此外表示MgCl,
在催化剂存在下,任选在酸结合剂存在下并且任选在稀释剂存在下反应,或
(ii)式(I-b)的化合物
其中R1、R2、R4和m具有上述含义,
X2表示-B(OH)2、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、Sn(nBu)3或ZnCl,
与式(III)的芳香化合物
T-A (III)
其中
A表示任选被列于W1的基团一或多取代的苯基,
其中W1具有上述含义,和
T表示Cl、Br、I、-OSO2CF3、-OSO2(CF2)3CF3,
在催化剂存在下,任选在酸结合剂存在下并且任选在稀释剂存在下反应,或
(iii)式(I-a)的化合物
其中
R1、R2、R4、X1和m具有上述含义,
与式(III)的芳香化合物
T-A (III)
其中
A和T具有上述含义,
在催化剂存在下,在4,4,4′,4′,5,5,5′,5′-八甲基-2,2′-双-1,3,2-二氧杂硼杂环戊烷或在5,5,5′,5′-四甲基-2,2′-双-1,3,2-二氧杂硼杂环己烷或在4,4,4′,4′,6,6′-六甲基-2,2′-双-1,3,2-二氧杂硼杂环己烷或在2,2′-双-1,3,2-苯并二氧杂硼杂环戊烯存在下和任选在酸结合剂存在下和任选在稀释剂存在下进行串联反应,
或
C)式(IV)的光学活性的氨基酮
其中
R1、R2、R3、R4和m具有上述含义,
通过用路易斯酸或质子酸处理脱保护并且使就地生成的胺在酸存在下环合。
最后,已发现,本发明的式(I)化合物具有很好的杀虫性能并且既能用于植物保护又能用于材料保护,以防治不希望的害虫,如昆虫。
令人惊奇的是,与也作为具有杀虫性能的高活性化合物已知的、相应的外消旋体以及与(S)构型的类似物相比,本发明式(I)化合物具有明显好的杀虫活性。
令人惊奇的是,从所测试的许多可商购的固相中选出的在方法(A)中使用的用于分离式(I-rac)的外消旋化合物的柱材料是唯一以高纯度和高产率提供相应的对映体的材料。
本发明化合物通过式(I)一般定义。在上述和下述提到的结构式中列出的基团的优选的取代基或范围在下面说明。
m
优选表示0、1、2或3。
R1 优选表示氟、氯、溴或甲基。
R2 优选表示氢、氟、氯或溴。
R3 优选表示氢、氟、氯、溴、碘、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-卤代烷基、C2-C6-卤代链烯基、C1-C6-烷氧基、-S(O)oR6、-OSO2R6、二(C4-C8-烷氧基)甲硼烷、-B(OH)2或表示任选被列于W1的基团一或多取代的苯基。
R4 优选表示卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基或-S(O)oR6。
W1 优选表示氰基、卤素、羟基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C6-卤代链烯基氧基、C1-C6-烷氧基羰基、三(C1-C4-烷基)甲硅烷基、三(C1-C4-烷基)甲硅烷基氧基、-S(O)oR6或-SO2NR7R8。
o
优选表示0、1或2。
R6 优选表示氢、C1-C6-烷基或C1-C6-卤代烷基。
R7和R8相互独立
优选表示氢、C1-C6-烷基、C1-C6-卤代烷基或一起表示C2-C6-亚烷基或C1-C4-烷氧基-C1-C4-亚烷基(例如吗啉)。
m
特别优选表示0、1或2。
R1 特别优选表示氟、氯或甲基。
R2 特别优选表示氢、氟或氯。
R3 特别优选表示氢、氟、氯、溴、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基;表示各自被氟或氯取代的C1-C6-烷基或C2-C6-链烯基;表示-S(O)oR6、-OSO2R6、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、-B(OH)2或表示任选被列于W1的基团一至三取代的苯基。
R4 特别优选表示氟、氯、溴、C1-C6-烷基、C1-C6-烷氧基,各自被氟或氯取代的C1-C6-烷基或C1-C6-烷氧基或表示-S(O)oR6。
W1 特别优选表示氰基、氟、氯、溴、碘、羟基、C1-C4-烷基、C1-C4-烷氧基,各自被氟或氯取代的C1-C4-烷基、C1-C4-烷氧基、C2-C6-链烯基氧基,表示C1-C4-烷氧基羰基、-OSi(Me2)t-Bu、-S(O)oR6或-SO2NR7R8。
o
特别优选表示0、1或2。
R6 特别优选表示氢、C1-C6-烷基或表示被氟或氯取代的C1-C4-烷基。
R7和R8相互独立
特别优选表示氢、C1-C6-烷基、被氟或氯取代的C1-C6-烷基,或一起表示C4-C5-亚烷基。
m
非常特别优选表示0、1或2。
R1 非常特别优选表示氟、氯或甲基。
R2 非常特别优选表示氢、氟或氯。
R3 非常特别优选表示氢、氯、溴、羟基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-丙烯基、丁烯基、炔丙基、丁炔基、甲氧基、乙氧基、正丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、-SO2CF3、-SO2(CF2)3CF3、-OSO2CF3、-OSO2(CF2)3CF3、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、-B(OH)2或表示被氟或氯取代的C1-C4-烷基或表示任选被列于W1的基团一至三取代的苯基。
此外,R3 非常特别优选表示异丙氧基。
R4 非常特别优选表示氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基、二氟甲氧基、三氟甲氧基或-SO2CF3。
W1 非常特别优选表示氰基、氟、氯、溴、羟基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、正丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基、二氟甲氧基、-CF3、-CHF2、-CClF2,-CF2CHFCl、-CF2CH2F、-CF2CCl3、-CH2CF3、-CF2CHFCF3、-CH2CF2H、-CH2CF2CF3、-CF2CF2H、-CF2CHFCF3、-OCF2CF2H、-OCF=CF2、-SCF3、-SOCF3、-SO2CF3、-SCHF2、-SOCHF2、-SO2CHF2、-OSi(Me2)t-Bu、-SO2NMe2或-CO2Et。
此外W1 非常特别优选表示异丙氧基。
此外优选的是式(I-c)、(I-d)、(I-e)、(I-f)和(I-g)的化合物
其中,在各种情况下
R3具有上述含义和R4-1表示氢、甲氧基或乙氧基。
此外优选的是式(I-h)、(I-i)、(I-j)、(I-k)和(I-1)的化合物。
其中各W1具有上述含义。
在上述定义中,氧基亚烷基或硫基亚烷基表示-O-烷基-或-S-烷基-并且亚烷基氧基或亚烷基硫基表示-烷基-O-或-烷基-S-,氧基亚烷基氧基表示-O-烷基-O-。
优选、特别优选或非常特别优选的是带有优选、特别优选或非常特别优选的取代基的化合物。
饱和或不饱和烃基,如烷基或链烯基,包括与杂原子相连的,如烷氧基,只要可能,可以各自是直链或支链的。
任选被取代的基团可以是一或多取代的,其中,在多取代的情况下,所述取代基可以相同或不同。用相同符号表示的多个基团,例如m个R4对于m>1,可以相同或不同。
但上述一般和优选范围所述的基团定义或说明也可以相互任意组合,包括各范围和优选范围之间的组合。它们既适用于最终产物,又适用于前体和中间体。
方法和中间体的说明:
方法A
在实施本发明方法A中作为原料所需的外消旋化合物通过式(I-rac)进行一般定义。在该结构式中R1、R2、R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
在实施本发明方法A中所用的式(I-rac)外消旋化合物是已知的并且可按已知方法制备(WO 00/21958、WO 99/59968、WO 99/59967和WO 98/22438)。
按制备色谱法,优选按照高效液相法(HPLC)实施本发明方法A。对此应用手性硅胶固定相,已证明用三(3,5-二甲基苯基氨基甲酸酯)-纤维素改性的硅胶特别适合于将式(I-rac)化合物分离成两对映体。该分离材料可商购。但是,也可应用其它固定相作为色谱材料。
方法B
如果用(2R)-5-(2,6-二氟苯基)-2-(4-三氟甲基磺酰基氧基-苯基)-3,4-二氢-2H-吡咯、4-三氟甲氧基苯基硼酸和钯催化剂作原料,那么本发明方法B(i)通过下述反应路线表示。
如果用(2R)-5-(2,6-二氟苯基)-2-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯基]-3,4-二氢-2H-吡咯、4-三氟甲氧基-溴苯和钯催化剂,那么本发明方法B(ii)通过下述反应路线表示。
如果用(2R)-5-(2,6-二氟苯基)-2-(4-溴苯基)-3,4-二氢-2H-吡咯、4-三氟甲氧基-溴苯、钯催化剂和4,4,4′,4′,5,5,5′,5′-八甲基-2,2′-二-1,3,2-二氧杂硼杂环戊烷作原料,那么本发明方法B(iii)通过下述反应路线表示。
在实施本发明方法B中作原料所需的化合物通过式(I-a)和(I-b)一般性定义,在这些结构式中R1、R2、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
X1 优选表示Cl、Br、-OSO2CF3或-OSO2(CF2)3CF3。
X1 特别优选表示Cl、Br或-OSO2CF3。
X1 非常特别优选表示Cl、Br或-OSO2CF3。
X2 优选表示-B(OH)2、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、Sn(nBu)3或ZnCl。
X2 特别优选表示-B(OH)2、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基或1,3,2-苯并二氧杂硼杂环戊烯-2-基。
X2 非常特别优选表示-B(OH)2、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基或(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基。
对此,基团R6、R7和R8优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(I-a)和(I-b)的光学活性环亚胺是新化合物并类似于方法A或C制备。
在实施本发明方法B(i)中作为原料所需的金属有机化合物通过式(II)一般性定义。
A
优选表示未取代的或被列于W1的基团一至四取代的苯基。
A
特别优选表示未取代的或被列于W1的基团一至二取代的苯基。
A
非常特别优选表示被列于W1的基团一至二取代的苯基。
对此,W1优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
M
优选表示-B(OH)2、Sn(nBu)3或ZnCl。
M此外
优选表示MgCl。
M
特别优选表示-B(OH)2或Sn(nBu)3。
M
非常特别优选表示-B(OH)2。
式(II)金属有机化合物部分是已知的,例如硼酸[例如当M=-B(OH)2时]也可以由(溴代)芳香化合物通过锂化或Br-Li(Mg)置换并随后与三烷氧基硼化合物反应制备(参见例如Tetrahedron Lett.1993,34,8237-8240)。
在实施本发明方法B(ii)和B(iii)中作为原料所需的芳香化合物通过式(III)一般性定义。对此,A优选、特别优选或非常特别优选表示已在式(II)化合物的描述中提到的优选、特别优选或非常特别优选的含义。
T
优选表示Cl、Br、-OSO2CF3或-OSO2(CF2)3CF3。
T
特别优选表示Cl、Br或-OSO2CF3。
T
非常特别优选表示Br或-OSO2CF3。
式(III)的芳香化合物一般是已知的或可商购。
本发明方法B(iii)可以两种变种进行,或者加入式(I-a)化合物或者加入式(III)化合物。方法B(iii)可以看成是方法B(i)和B(ii)的串联反应。
在实施本发明方法(B)中一般加入钯催化剂,该催化剂又在可加入或不加其它的配体的情况下应用。作为催化剂优选应用PdCl2(dppf)[dppf=1,1′-二(二苯基膦基)二茂铁]、Pd(PPh3)4、PdCl2(PPh3)2、PdCl2(CH3CN)2、Pd2(dba)3[dba=二亚苄基丙酮]或Pd(OAc)2。特别优选PdCl2(dppf)、Pd(PPh3)4、PdCl2(PPh3)2或Pd(OAc)2,非常特别优选PdCl2(dppf)或Pd(PPh3)4。
在实施本发明方法B(i)中尤其非常特别优选PdCl2(dppf)、Pd(PPh3)4或Pd(OAc)2。
在实施本发明方法B(ii)中尤其非常特别优选使用Pd2(dba)3。
在实施本发明方法B(iii)中,尤其非常特别优选在串联反应的第一步中使用PdCl2(dppf),在第二步中使用PdCl2(dppf)、Pd(PPh3)4或Pd(OAc)2。
配体可以是三芳基膦,、三烷基膦或砷。优选用dppf、PPh3、P(t-Bu)3、Pcy3或AsPh3,特别优选dppf。
式(I)化合物可由式(I-b)化合物[X2=(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基]类似于已知方法制备(J.Org.Chem.1995,60,7508;Tetrahedron Lett.1997,38,3841)。
方法C
如果用叔丁基-(1R)-4-(2,6-二氟苯基)-4-氧代-1-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁基氨基甲酸酯和三氟乙酸作用原料,那么本发明方法(C)可以通过下述反应路线表示:
在实施本发明方法C中作原料所需的氨基酮通过式(IV)一般性定义。在该结构式中,R1、R2、R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(IV)的光学活性氨基酮是新化合物,
其中R1、R2、R3、R4和m具有上述含义。该化合物可如下制备:
α)式(V)的光学活性的N-Boc-内酰胺
其中R3、R4和m具有上述含义,
与式(VI)的金属化芳香化合物在稀释剂存在下于-70℃-+70℃温度下反应,
其中R1和R2具有上述含义,和
M1表示Li、MgCl、MgBr、MgI、ZnCl。
在实施本发明方法α中作原料所需的金属化芳香化合物通过式(VI)一般性定义。在该结构式中,R1和R2优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。M1优选表示Li、MgCl、MgBr、MgI、ZnCl,特别优选表示Li、MgCl、MgBr、MgI,非常特别优选表示Li、MgCl、MgBr。
式(VI)的金属化芳香化合物部分是已知的或按已知方法,例如锂化或格氏反应,通过相应的芳香化合物或卤代芳香化合物制备。
在实施方法α中作原料所需的N-Boc-内酰胺通过式(V)一般性定义,在该结构式中,R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(V)的N-Boc-内酰胺是新化合物,它可如下制备:
β)式(VII)的光学活性内酰胺
其中
R3、R4和m具有上述含义,
按常规方法,例如与二叔丁基二碳酸酯在碱存在下反应(参见Tetrahedron Lett.1998,39,2705-2706)。
在实施方法β中作原料所需的内酰胺通过式(VII)一般性定义,在该结构式中,R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(VII)的光学活性内酰胺是新化合物,它可通过如下制备:
γ)式(VII-rac)的外消旋内酰胺
其中
R3、R4和m具有上述含义,
在手性硅胶固定相上色谱纯化并在减压下浓缩洗脱液,或
δ)式(VIII)的γ-酮酸
其中
R3、R4和m具有上述含义,
在多步合成中反应,
或
ε)式(VIII-a)的γ-酮酸酯
其中
R表示烷基,和
R3、R4和m具有上述含义,
在多步合成中反应。
在实施方法γ中作原料所需的外消旋内酰胺通过式(VII-rac)一般性定义,在该结构式中,R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(VII-rac)的外消旋内酰胺是已知的,并且可按照已知的方法制备(WO 99/59968、WO 99/59967和WO 98/22438)。
按制备色谱法,优选按照高效液相法(HPLC)实施本发明方法γ。对此应用手性硅胶固定相,已证明用N-甲基丙烯酰基-L-亮氨酸-D-基酰胺改性的硅胶衍生物(例如巯基丙基硅胶)特别适合用于分离式(VII-rac)化合物。该分离材料是已知的(参见EP-A 0 379 917)。
令人惊奇的是,式(VII-rac)的外消旋内酰胺可以在较小的柱子[450mm×75mm,(I.D.)]上、在短的时间内(梯度洗脱小于20min)以千克规模通过多次色谱分离。与常规可得的手性固定相相比,所用的材料具有明显较高的对映选择性值α(α=16相对于α=3-4;α值越大,对映体相互之间的分离效果越好)。
本发明的多步方法δ可用下列的反应路线表示。
式(VIII)的γ-酮酸与2(S)-2-氨基-2-苯基乙醇缩合得到主要以非对映体形式的式(IX)的二环内酰胺。
式(IX)的二环内酰胺在路易斯酸(例如TiCl4)和还原剂(例如Et3SiH)存在下的还原裂解得到式(X)的N-保护的γ-内酰胺(参见J.Org.Chem.1992,57,1656)。
式(X)的γ-内酰胺的羟基可以通过用氯化剂(例如亚硫酰氯)处理转化成离去基团(特别是氯原子,参见Tetrahedron Asymmetry1996,7,1835),由此得到了式(XI)的氯化物。
通过用碱(例如KOtBu)处理,式(XI)脱氯化氢得到式(XII)的N-乙烯基内酰胺。
式(X)的γ-内酰胺可例如通过用碱(例如LiOH)在合适的溶剂(例如DMSO)中于60℃-140℃温度下处理也可直接转化成式(XII)的N-乙烯基内酰胺(参见J.Org.Chem.1996,61,5813)。
(XII)的酸水解(例如用1M HCl)得到式(VII)的γ-内酰胺(参见J.Org.Chem.1996,61,5813)。
在实施本发明方法δ中作原料所需的γ-酮酸通过式(VIII)一般性定义,中间体通过式(IX)、(X)、(XI)和(XII)一般性定义。在这些结构式中R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(VIII)的γ-酮酸部分是已知的,它们可以通过部分已知的方法制备。例如通过相应的芳香化合物与琥珀酸酐或琥珀酸单酯酰氯,在路易斯酸(例如氯化铝)存在下和任选在稀释剂(例如1,2-二氯乙烷)存在下反应得到式(VIII)的γ-酮酸(参见例如Org.Prep.Proced.Int.1995,27,550-552)。
对于不能Friedel-Crafts-酰化的芳香化合物,另外可以使用相应的有机金属衍生物,如格氏试剂(参见Syn.Commun.1996,26,3897)。
式(VIII)的γ-酮酸也可如下制备,即通过式(XIII)的α,β-不饱和羰基化合物,例如通过应用锌粉在乙酸中按下述反应路线还原(参见Chem.Pharm.Bull.1988,36,2050)。
所述羰基化合物通过式(XIII)一般性定义。在该结构式中R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(XIII)的α,β-不饱和羰基化合物部分是已知的和/或可例如通过式(XIV)的乙酰苯与乙醛酸在碱(例如NaOH)存在下和任选在稀释剂(例如水、EtOH)存在下按下述反应路线缩合制备(参见例如J.Med.Chem.1996,39,4396)。
所述乙酰苯通过式(XIV)一般性定义,在该结构式中R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。式(XIV)乙酰苯是已知的。
所述多步方法ε可通过下述反应路线表示:
式(VIII-a)的γ-酮酸酯与烯丙基胺在氯化铵存在下反应得到式(XV)烯丙基酰胺(参见Houben-Weyl,Methoden der OrganischenChemie,第4版,第VIII卷,第6章,第653页起)。
式(XV)化合物中的酮官能团可按照Corey,Bakshi & Shibata-Protokoll(CBS-还原)在催化剂{例如(3aR)-1-甲基-3,3,6-三苯基四氢-3H-吡咯并[1,2-c][1,3,2]氧杂氮杂硼杂环戊烯,可商购}存在下对映选择性地被还原(参见Angew.Chem.1998,110,2093和其中所引文献)。
式(XVI)化合物随后生成式(XVII)的N-烯丙基内酰胺的环合通过用KOtBu双脱质子化并与甲苯磺酰氯反应完成(参见Synth.Commun.1988,18,1159)而没有可检测到的立体化学损失。令人惊奇的是与文献相比可省去作为助溶剂的致癌的六甲基磷酸三酰胺(HMPT)的应用。
烯丙基保护基的裂解在THF水溶液中,在甲苯磺酸存在下,在加入10mol%Pd(Ph3P)4的情况下进行(参见Heterocycles 1997,44,213和其中所引的文献),由此得到式(VII)的内酰胺。所希望的对映体的富集可通过在石油醚(40/60)/甲苯中重结晶进行。
在实施本发明方法ε中作原料所需的γ-酮酸酯通过式(VIII-a),中间体通过式(XV)、(XVI)和(XVII)一般性定义。在这些结构式中R3、R4和m优选、特别优选或非常特别优选表示已在与本发明式(I)化合物相关的描述中提到的这些基团优选、特别优选或非常特别优选的含义。
式(VIII-a)的γ-酮酸酯可由式(VIII)相应的酸按照已知的酯化方法制备。
在各种情况下,在实施本发明方法(B)中的酸结合剂可以是用于这类反应所有常用的无机和有机碱。优选可应用的是碱土金属-或碱金属氢氧化物,如氢氧化钠、氢氧化钙、氢氧化钾或也可以是氢氧化铵,碱金属碳酸盐,如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠,碱金属或碱土金属乙酸盐,如乙酸钠、乙酸钾、乙酸钙,碱金属氟化物,以及叔胺,如三甲胺、三乙胺、三丁基胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。但也可以不另加酸结合剂进行,或加入过量的胺组分,以使其同时起酸结合剂的功能。特别优选用氢氧化钡、磷酸三钾、碳酸铯、碳酸钾、碳酸钠、乙酸钾、三乙胺、KOtBu、氟化铯或氟化钾。
在各种情况下,在实施本发明方法(B)和(C)中的稀释剂可以是所有常规的惰性有机溶剂。优选可应用任选卤素取代的脂肪族、脂环族或芳香族烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯甲烷、二氯乙烷或三氯乙烷;醚,如乙醚、二异丙基醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈,如乙腈、丙腈、正-或异丁腈或苄腈;酰胺,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基N-甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酸三酰胺;酯,如乙酸甲酯或乙酸乙酯,亚砜,如二甲基亚砜或砜,如环丁砜。
在各种情况下,在实施本发明方法(A)中的洗脱剂可以是所有常规的惰性有机溶剂以及这些溶剂的混合物。优选可应用任选被卤素取代的脂肪族、脂环族或芳香族烃,如石油醚、己烷、庚烷、环己烷;二氯甲烷、氯仿;醇类,甲醇、乙醇、丙醇;腈类,如乙腈;酯,如乙酸甲酯或乙酸乙酯。特别优选应用脂肪族烃,如己烷或庚烷,和醇类,如甲醇或丙醇,非常特别优选正庚烷和异丙醇或它们的混合物。
在实施本发明方法(B)中应用的稀释剂特别优选丙酮、二甲氧基乙烷、二噁烷、THF、DMF、二甲基乙酰胺、DMSO、乙醇、甲苯或任选这些所述稀释剂与水的混合物。
在实施本发明方法(C)中应用的稀释剂特别优选二氯甲烷、氯仿、甲苯、甲醇或乙醇。
在各种情况下,在实施本发明方法(C)中可应用所有常规的路易斯酸或质子酸。Boc-裂解的方法一般是已知的(参见例如T.W.Greene,P.G.M.Wuts,Protective Groups in Organic Synthesis,第3版,New York,Wiley & Sons,1999,第520-525页)。优选用三氟乙酸、HCl或HBr裂解掉Boc-保护基。
在各种情况下,在实施本发明方法(A)中的反应温度可以在较大的范围内变化,一般为10℃-60℃,优选10℃-40℃,特别优选在室温下进行。
在各种情况下,在实施本发明方法(B)中的反应温度可以在较大的范围内变化,一般为0℃-140℃,优选10℃-120℃,特别优选在20℃-120℃下进行。
在各种情况下,在实施本发明方法(C)中的反应温度可以在较大的范围内变化,一般为-20℃-+120℃,优选-10℃-60℃。
在实施本发明方法A中,一般将(I-rac)的外消旋化合物的约1%的溶液用于色谱分离。但也可应用其它的浓度。后处理按常规方法进行。一般如此进行,即尽可能地浓缩洗脱液,过滤固体成分,用正庚烷洗涤并干燥。任选通过色谱纯化残余物以除去可能还存在的杂质。对此,用正己烷或环己烷和乙酸乙酯的混合物作为洗脱剂,其组成必须与在各种情况下要纯化的化合物相适应。
在实施本发明方法B(i)中,对于1Mol式(I-a)化合物一般加入1Mol或稍微过量的式(II)金属有机化合物。但也可以以其它比例应用这些反应组分。后处理按常规方法进行。一般如此进行,即用乙酸乙酯处理反应混合物并用水洗涤该有机相,用硫酸钠干燥,过滤并浓缩。残余物任选按常规方法例如色谱法或重结晶以除去可能还存在的杂质。
在实施本发明方法B(ii)中,对于1Mol式(I-b)化合物一般加入1Mol或稍微过量的式(III)芳香化合物。但也可以以其它比例应用这些反应组分。后处理按常规方法进行。一般如此进行,即用乙酸乙酯处理反应混合物并用水洗涤该有机相,用硫酸钠干燥,过滤并浓缩。残余物任选按常规方法,例如色谱法或重结晶以除去可能还存在的杂质。
在实施本发明方法B(iii)中,对于1Mol式(I-a)化合物一般加入1Mol或稍微过量的二硼化合物和1Mol或稍微过量的式(III)(杂)芳香化合物以及3%的钯催化剂。但也可以以其它比例应用这些反应组分。可选择的是先加入式(I-a)或式(III)化合物。后处理按常规方法进行。一般如此进行,即用水稀释反应混合物,用乙酸乙酯萃取,用水洗涤该有机相,用硫酸钠干燥,过滤并浓缩。残余物任选按常规方法例如色谱法或重结晶以除去可能还存在的杂质。
在实施本发明方法(C)中,对于1Mol式(IV)化合物一般加入100Mol质子酸,但也可以以其它比例应用这些反应组分。后处理按常规方法进行。一般如此进行,即浓缩反应混合物,用适当溶剂处理,用氢氧化钠调到pH12并用水洗涤该有机相,用硫酸钠干燥,过滤并浓缩。残余物任选按常规方法例如色谱法或重结晶以除去可能还存在的杂质。
本发明活性化合物适合防治害虫,特别是在农业、林业、储藏产品和材料的保护以及卫生领域中发生的昆虫、螨类和线虫,同时具有良好的植物相容性和有益的对温血动物的毒性。优选可将它们用作植物保护剂。它们对普通敏感和抗性种类以及对所有或单个发育阶段都具有活性。上述有害动物包括:
等足目,例如,潮虫(Oniscus asellus)、平甲虫、鼠妇。
倍足目,例如,具斑马陆。
唇足目,例如,食果地蜈蚣、蚰蜒属。
综合目,例如,庭园么蚰。
缨尾目,例如,台湾衣鱼。
弹尾目,例如,武装棘跳虫。
直翅目,例如,家蟋蟀、蝼蛄属、非洲飞蝗、黑蝗属、沙漠蝗。
蜚蠊目,例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊。
革翅目,例如,欧洲球螋。
等翅目,例如,散白蚁属。
虱目,例如,体虱、血虱属、颚虱属、嚼虱属、畜虱属。
缨翅目,例如,温室条蓟马、烟蓟马、棕榈蓟马、苜蓿蓟马。
异翅亚目,例如,扁盾蝽属、棉红蝽(Dysdercus intermedius)、方背皮蝽、温带臭虫、长红猎蝽、椎猎蝽属。
同翅目,例如,甘蓝粉虱、甘薯粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶 隐瘤蚜、豆卫矛蚜、苹果蚜、苹果绵蚜、桃大尾蚜、葡萄根瘤蚜、瘿绵蚜属、麦长管蚜、瘤蚜属、忽布疣蚜、禾谷缢管蚜、绿小叶蝉属、殃叶蝉(Euscelis bilobatus)、黑尾叶蝉、欧果坚球蚧、榄珠蜡蚧、灰飞虱、褐飞虱、红肾圆盾蚧、常春藤圆盾蚧、粉蚧属、木虱属。
鳞翅目,例如,棉红铃虫、松粉蝶尺蛾、果园秋尺蛾、潜叶细蛾(lithocolletis blancardella)、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾(Bucculatrix thurberiella)、柑橘潜叶蛾、地夜蛾属、切夜蛾属、脏切夜蛾、埃及钻夜蛾、实夜蛾属、甘蓝夜蛾、小眼夜蛾、灰翅夜蛾属、粉纹夜蛾、苹果蠹蛾、粉蝶属、禾草螟属、玉米螟、地中海粉斑螟、蜡螟、幕谷蛾、袋谷蛾、褐织蛾、黄尾卷叶蛾、烟卷蛾(Capua reticulana)、云杉色卷蛾、葡萄果蠹蛾、茶长卷蛾、栎绿卷蛾、Cnaphalocerus属、水稻负泥虫。
鞘翅目,例如,家具窃蠹、谷蠹、豆象(Bruchidius obtectus)、菜豆象、北美家天牛、蓝毛臀萤叶甲、马铃薯叶甲、辣根猿叶甲、条叶甲属、油菜金头跳甲、墨西哥豆瓢虫、隐食甲属、锯谷盗、花象属、米象属、葡萄黑耳喙象、香蕉根颈象、种子象、紫苜蓿叶象、皮蠹属、斑皮蠹属、圆皮蠹属、毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、宽胸叩甲属、五月鳃金龟、马铃薯鳃金龟、褐新西兰肋翅鳃角金龟、稻水象。
膜翅目,例如,松叶蜂属、实叶蜂属、毛蚁属、小家蚁、胡蜂属。
双翅目,例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、螫蝇属、狂蝇属、皮蝇属、虻属、螗蜩属(Tannia spp.)、花园毛蚊、瑞典麦杆蝇、草种蝇属、菠菜泉蝇、地中海实蝇、油橄榄果实蝇、沼泽大蚊、种蝇属、斑潜蝇属。
蚤目,例如,印鼠客蚤、角叶蚤属。
蛛形纲,例如,蝎(Scorpio maurus)、红斑蛛、粗脚粉螨、锐缘蜱属、纯缘蜱属、鸡皮刺螨、兔瘿螨、柑橘皱叶刺瘿螨、牛蜱属、扇头蜱属、花蜱属、璃眼蜱属、硬蜱属、瘙螨属、瘁螨属、疥螨属、跗线螨属、苜蓿苔螨、全爪螨属、叶螨属、半跗线螨属、短须螨属。
植物寄生线虫包括,例如短体线虫属、相似穿孔线虫、起绒草茎线虫、半穿刺线虫、异皮属、球异皮属、根结属、滑刃线虫属、长针线虫属、剑线属、毛刺属、伞滑刃线虫属。
特别地,本发明式(I)化合物具有优良的抗毛虫、甲虫幼虫、蛛螨、蚜虫和潜叶蝇(Minierfliegen)活性.
本发明化合物可任选以特定浓度或用量应用,在作为除草剂和杀微生物剂,例如作为杀真菌剂、杀霉菌剂和杀菌剂时,也是如此。也可任选将它们用于合成其它活性物质的中间体或前体。
根据本发明,可以处理所有植物和植物各部分。此处植物可以理解为所有植物以及植物群落如需要和不需要的野生植物或农作物(包括自然长出的农作物)。农作物可以是通过常规植物育种和优化方法或通过生物技术和重组方法或上述方法的结合获得的植物,包括转基因植物以及包括可获得或不能获得植物品种保护的植物品种,植物的各部分应理解为植物的所有地上和地下部分以及器官,如茎、叶、花和根,可提及的实例为叶片、针叶、叶柄、树干、花、子实体、果实、种子、根、块茎和根状茎。植物各部分还包括收获材料以及无性和有性繁殖材料,例如插条、块茎、根状茎、压枝和种子。
采用活性化合物进行植物和植物各部分的本发明处理方法是通过常规处理方法直接施用或将化合物作用于它们的环境、栖息地或贮藏区进行处理,例如浸渍、喷雾、熏蒸、弥雾、撒播、刷涂以及在繁殖材料特别是种子的情况下还可以进行一层或多层包衣。
可将本发明活性化合物转化成为常规制剂如溶液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉剂、颗粒剂、浓悬浮乳剂、用活性化合物浸渍的天然和合成材料以及聚合物包封的微胶囊剂。
这些制剂是以已知方法制备的,例如通过将本发明活性化合物与填充剂,即液体溶剂和/或固体载体混合而生产,制剂中任选使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适合的液体溶剂主要有:芳香烃类,如二甲苯、甲苯或烷基萘;氯代芳烃类或氯代脂肪烃类,如氯苯、氯乙烯或二氯甲烷;脂肪烃类,如环己烷或链烷烃,例如矿物油馏份、矿物油和植物油;醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适合的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅、氧化铝和硅酸盐;适合颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉末颗粒,以及有机材料的颗粒如锯末、坚果壳、玉米穗茎和烟草茎;
适合的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,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水解产物;
适合的分散剂有:例如木素亚硫酸废液和甲基纤维素。
在制剂中还可使用粘着剂如羧甲基纤维素和粉末、颗粒或胶乳状的天然或合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂如脑磷脂和卵磷脂和合成磷脂。其它添加剂可以是矿物油和植物油。
可以使用着色剂如无机颜料,例如氧化铁、氧化钛和普鲁士兰,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和痕量营养物如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1-95%,优选0.5-90%的活性化合物。
本发明活性化合物可以其本身或以其制剂的形式也可以与其它的已知活性化合物混合应用,其它已知活性化合物如杀虫剂、引诱剂、消毒剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、植物生长调节剂或除草剂,以例如拓宽作用谱或避免产生抗性。对此,在很多情况下可以获得协同作用,即混合物的活性大于单一组分的活性。杀虫剂包括,例如磷酸酯、氨基甲酸酯、羧酸酯、卤代烃类、苯基脲类和从微生物中生产的物质等。
作为共混组分可以是例如下述化合物:
杀真菌剂:
Aldimorph,氨丙膦酸、氨丙膦酸钾、Andoprim、敌菌灵、戊环唑、腈嘧菌酯
苯霜灵、麦锈灵、苯菌灵、苄烯酸、苄烯酸-异丁酯、双丙氨酰膦、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌素、磺嘧菌灵、粉病定,
石硫合剂、Capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、Carvon、灭螨锰、灭瘟唑、苯咪唑菌、地茂散、氯化苦、百菌清、乙菌利、Clozylacon、硫杂灵、清菌脲、环唑醇、环丙嘧啶、酯菌胺,
双乙氧咪唑威、双氯酚、苄氯三唑醇、Diclofluanid、哒菌清、氯硝胺、乙霉威、噁醚唑、甲菌定、烯酰吗啉、烯唑醇、烯唑醇-M、敌螨普、二苯胺、吡菌硫、灭菌磷、二噻农、吗菌灵、多果定、敌菌酮,
克瘟散、氧唑菌、乙环唑、乙菌定、氯唑灵,
噁唑酮菌、菌拿灵、异嘧菌醇、腈苯唑、呋菌胺、种衣酯、拌种咯、苯锈定、丁苯吗啉、薯瘟锡、毒菌锡、福美铁、嘧菌腙、氟定胺、氟联苯菌(Flumetover)、氟菌安、喹唑菌酮、调嘧醇、氟硅唑,磺菌胺、氟酰胺、粉唑胺、灭菌丹、藻菌磷(Fosetyl-Aluminium)、藻菌磷(Fosetyl-Natrium)、四氯苯酞、麦穗宁、呋氨丙灵、呋吡唑灵、灭菌安(Furcarbonil)、呋菌唑、呋醚唑、拌种胺,
双胍辛醋酸酯,
六氯苯、己唑醇、噁霉灵,
烯菌灵、酰胺唑、双胍辛(Iminoctadin)、双胍辛对十二烷基苯磺酸盐(Iminoctadinealbesilate)、双胍辛醋酸盐、Iodocarb、环戊唑醇、异稻瘟腈(IBP)、异丙定、Irumamycin、富士一号、氯苯咪菌酮,
春雷霉素、亚胺菌、铜制品,如,氢氧化铜、环烷酸铜、王铜、硫酸铜、氧化铜、喹啉铜、和碱式硫酸铜混合物,
锰铜混剂、代森锰锌、代森锰、Meferimzone、嘧菌胺、丙氧灭锈胺、甲霜灵、环戊唑菌、磺菌威、甲呋菌胺、代森联、苯吡洛菌(Metomeclam)、Metsulfovax、米多霉素、腈菌唑、甲菌利。
福美镍、异丙消、氟苯嘧啶醇,
甲呋酰胺、噁霜灵、Oxamocarb、喹菌酮、氧化萎锈灵(Oxycarboxim)、Oxyfenthiin,
多效唑、稻瘟酯、戊菌唑、戊菌隆、双氯苯磷、Picoxystrobin、多马霉素、粉病灵、多氧霉素、Ployoxorim、噻菌灵、丙氯灵、杀菌利、百维灵、Propanosine-Natrium、丙环唑、甲基代森锌、Pyraclostrobin、定菌磷、啶斑肟、二甲嘧菌胺、咯喹酮、氯吡呋醚,
唑喹菌酮、五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇、叶枯酞、四氯硝基苯、调环烯、氟醚唑、涕必灵、噻菌腈、溴氟唑菌、甲基托布津、福美双、硫氰苯甲酰胺、甲基立枯磷、对甲抑菌灵、三唑酮、菌唑醇、叶锈特、唑菌嗪、杨菌胺、三环唑、克啉菌、Trifloxystrobin、氟菌唑、嗪氨灵、戊叉唑菌,
烯效唑,
有效霉素、烯菌酮、烯霜苄唑,
氰菌胺、代森锌、福美锌及
咪草酯G、OK-8705、OK-8801,
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-氟-β-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-α-甲基-1H-1,2,4-三唑-1-乙醇,
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1H-1,2,4-三唑-1-乙醇,
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮,
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺,
{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸-1-异丙基酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2′,6′-二溴-2-甲基-4′-三氟甲氧基-4′-三氟甲基-1,3-噻唑-5-(N-甲酰苯胺),
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基环丙烷甲酰胺,
2,6-二氯-5-(甲基硫基)-4-嘧啶基硫氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)-磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-去氧-4-O-(4-O-甲基-β-D-吡喃葡糖苷基)-α-D-吡喃葡糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴甲基)-戊烷二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲胺,
8-羟基喹啉硫酸盐,
9H-呫吨-9-甲酸-2-[(苯基氨基)-羰基]-酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二甲酸酯,
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺-4-[3-[4-(1,1-二甲基丙基)-苯基-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐,
[(4-氯苯基)-偶氮]-氰基乙酸乙酯,
碳酸氢钾,
甲烷四硫醇钠盐,
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯,
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷甲酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺,
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺,
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-苯磺酰胺,
N-(4-环己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(4-己基苯基)-1,4,5,6-四氢-2-嘧啶胺,
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-噁唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯-4,5-双(2-丙炔基氧基)-苯基]-N′-甲氧基-甲亚氨酰胺,
N-甲酰基-N-羟基-DL-丙氨酸-钠盐,
O,O-二乙基-[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯(ethylphosphoramidothioat),
O-甲基-S-苯基-苯基丙基硫代氨基磷酸酯,
1,2,3-苯并噻二唑-7-硫代羟酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1′(3′H)-异苯并呋喃]-3′-酮,
4-[3,4-二甲氧基苯基]-3-(4-氟苯基)-丙烯酰基]-吗啉
杀菌剂:
溴硝丙二醇、双氯酚、氯定、福美镍、春雷霉素、异噻菌酮、呋喃甲酸、土霉素、噻菌灵、链霉素、叶枯酞、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
阿维菌素、乙酰甲胺磷、啶虫脒、氟丙菊酯、棉铃威、涕灭威、涕灭砜威、甲体氯氰菊酯(Alphacypermethrin)、甲体氯氰菊酯(Alphamethrin)、双甲脒、齐墩螨素、AZ 60541、艾扎丁、甲基吡噁磷、谷硫磷A、谷硫磷M、三唑锡,
波林杆菌芽孢、Bacillus sphaericus、柯敌克菌、苏金杆菌、Baculoviruses、Beauveria bassiana、Beauveria tenella、噁虫成、丙硫克百威、杀虫磺、苯螨特、β-氟氯氰菊酯、联苯肼酯、联苯菊酯、Bioethanomethrin、生物氯菊酯、Bistrifluron、BPMC、溴硫磷A、合杀威、噻嗪酮、特嘧硫磷、丁酮威、丁基哒螨灵(Butylpyridaben),
硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、Chloethocarb、氯氧磷、氟唑虫清、毒虫畏、氟啶脲、氯甲硫磷、毒死蜱、毒死蜱M、Chlovaporthrin、Chromafenozide、Cis-Resmethrin、Cispermethrin、Clocythrin、除线威、四螨嗪、Clothianidine、杀螟腈、Cycloprene、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺,
溴氰菊酯、内吸磷M、内吸磷S、甲基内吸磷、丁醚脲、二嗪磷、敌敌畏、开乐散、除虫脲、乐果、甲基毒虫畏、苯虫醚、乙拌磷、碘酰丁二辛、苯氧炔螨,
Eflusilanate、Emamectin、右旋烯炔菊酯、硫丹、Entomopfthoraspp.、S-氰戊菊酯、乙硫苯威、乙硫磷、灭线磷、醚菊酯、特苯噁唑、乙嘧硫磷,
苯线磷、喹螨醚、苯丁锡、杀螟硫磷、苯硫威、Fenoxacrim、Fenoxycarb、甲氰菊酯、Fenpyrad、Fenpyrithrin、唑螨酯、氰戊菊酯、氟虫腈、啶蜱脲、Flubrocythrinate、氟环脲、氟氰戊菊酯、氟虫脲、Flutenzine、氟胺氰菊酯、地虫硫磷、丁苯硫磷、噻唑磷、Fubfenprox、呋线威,
颗粒层增殖病毒,
特丁苯酰肼、HCH、庚烯磷、氟铃脲、噻螨酮、烯虫乙酯,
吡虫啉、噁二唑虫、氯唑磷、异柳磷、噁唑磷、齐墩螨素,
核多面体病毒,
氯氟氰菊酯、虱螨脲,
马拉硫磷、灭蚜磷、四聚乙醛、甲胺磷、Metharhiziumanisopliae、Metharhizium flavoviride、杀扑磷、甲硫威、蒙五一五、灭多威、甲氧苯酰肼、速灭威、噁虫酮、速灭磷、米尔螨素、Milbenmycin、久效磷,
二溴磷、烯啶虫胺、硝虫噻嗪、双苯氟脲,
氧乐果、杀线威、亚砜磷,
Paecilomyces fumosoroseus、对硫磷A、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、嘧啶磷A、甲基嘧啶磷、丙溴磷、猛杀威、克螨特、残杀威、丙硫磷、发硫磷、吡蚜酮、吡唑硫磷、反灭虫菊、除虫菊、哒螨灵、Pyridathion、嘧螨醚、吡丙醚,
喹硫磷,
病毒唑(Ribavirin),
杀抗松、硫线磷、氟硅菊酯、艾克敌、Spirodiclofen、治螟磷、硫丙磷,
氟胺氰菊酯、双苯酰肼、吡螨胺、嘧丙磷(Tebupirimiphos)、氟苯脲、七氟菊酯、双硫磷、灭虫威、特丁磷、杀虫威、三氯杀螨砜、辛体氯氰菊酯、Thiacloprid、Thiamethoxam、蛾蝇腈、Thiatriphos、硫环杀、硫双威、久效威、敌贝特、溴氯氰菊酯、四溴菊酯、苯螨噻、唑蚜威、三唑磷、Triazuron、Trichlophenidine、敌百虫、杀灵脲、混杀威,
蚜灭磷、氟吡唑虫、麦柯特尔,
YI 5302,
Zeta-cypermethrin、Zolaprofos,
2,2-二甲基环丙烷甲酸(1R-顺)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)呋喃亚基)-甲基]酯,
2,2,3,3-四甲基环丙烷甲酸[(3-苯氧基苯基)-甲基]酯,
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺,
2-(2-氯-6-氟苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰基氧基)-3-十二烷基-1,4-萘二酮,
2-氯-N-[[[4-(1-苯基乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)-苯基]-氨基]-羰基]苯甲酰胺,
丙基氨基甲酸(3-甲基苯基)酯,
4-[4-(4-乙氧基苯基)-4-甲基戊基]-1-氟-2-苯氧基-苯,
4-氯-2-(1,1-二甲基乙基)-5-[[2-(2,6-二甲基-4-苯氧基苯氧基)乙基]硫基]-3(2H)-哒嗪酮,
4-氯-2-(2-氯-2-甲基丙基)-5-[(6-碘-3-吡啶基)甲氧基]-3(2H)-哒嗪酮,
4-氯-5-[(6-氯-3-吡啶基)甲氧基]-2-(3,4-二氯苯基)-3(2H)哒嗪酮,
苏云金杆菌菌株EG-2348,
苯甲酸[2-苯甲酰基-1-(1,1-二甲基乙基)-酰肼,
丁酸[2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4.5]癸-3-烯-4-基]酯,
[3-[(6-氯-3-吡啶基)甲基]-2-噻唑烷亚基]-氨基氰,
二氢-2-(硝基亚甲基)-2H-1,3-噻嗪-3(4H)-甲醛,
[2-[[1,6-二氢-6-氧代-1-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯,
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸,
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺,
N-[(2-氯-5-噻唑基)甲基]-N′-甲基-N″-硝基-胍,
N-甲基-N′-(1-甲基-2-丙烯基)-1,2-肼二硫代甲酰胺,
N-甲基-N′-2-丙烯基-1,2-肼二硫代甲酰胺,
O,O-二乙基-[2-(二丙基氨基)-2-氧代乙基]-乙基硫代氨基磷酸酯,
N-氰基甲基-4-三氟甲基烟酰胺,
3,5-二氯-1-(3,3-二氯-2-丙烯基氧基)-4-[3-(5-三氟甲基吡啶-2-基氧基)-丙氧基]-苯。
还可与其它已知活性化合物如除草剂或与肥料和植物生长调节剂混合。
当用作杀虫剂时,本发明活性化合物还可以其市售通用制剂和从上述制剂制备的应用形式,与增效剂混合使用。增效剂是能够增加活性化合物活性,但加入的增效剂本身不必须有活性的化合物。
从市售通用制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。使用形式中活性化合物的浓度为0.0000001至95重量%的活性化合物,优选0.0001至1重量%。
本发明化合物以适合于以应用形式的常规方式施用。
当用于防治卫生害虫和储藏物品中的害虫时,所述活性化合物具有优异的木材和粘土残留活性以及对刷过石灰浆的基底具有很好的碱稳定性。
如上所提及,可按照本发明处理所有植物及其各部分。在一个优选的实施方案中,处理已有的或通过常规的生物育种方法,如杂交或原生质体融合得到的植物种类和植物品种和其各部分。在另一个优选的实施方案中,处理通过基因工程方法,任选与常规方法联合(基因修饰生物体)得到的转基因植物和植物品种及其各部分。术语“各部分”或“植物的各部分”或“植物部分”在上面已作过解释。
按照本发明,特别优选处理在各种情况下市售可得的或在使用的植物品种的植物。植物品种是指具有特定性能(“特性”)的植物,所述特性既可以通过常规育种、通过基因突变或通过重组DNA技术获得的。它们可以是栽培品种、生物和基因类型的。
根据植物种类或植物品种、它们的栖息地和生长条件(土壤、气候、植物生长期、营养),按照本发明的处理方法还可导致超加和的(“协同”)作用。因此,例如,可减少用量和/或拓宽活性谱和/或提高本发明所用的物质和组合物的活性、改善植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、提高收获量、提高收获产品的质量和/或提高产品的营养价值、提高产品的储存稳定性和/或可加工性,这些超出了本身所期望的效果。
属于按照本发明优选进行处理的转基因植物或植物品种(即通过基因工程得到的那些)包括通过基因材料的基因工程修饰得到的所有植物,所述基因修饰赋予这些植物特别有利的有用的性能(“特性”)。这种性能的例子是较好的植物生长、增强对高或低温的耐受性、增强对旱灾或水灾或土壤盐量的耐受性、增加花卉的性能、易于收获、加速成熟、较高的收获产量、收获产品较好的质量和/或较高的营养价值、收获产品较好的储存稳定性和/或可加工性。进一步和特别强调的所述性能的例子是提高植物对动物和微生物的害虫,如昆虫、螨、植物病菌真菌、细菌和/或病毒的抵御性,以及提高植物对某些除草活性化合物的耐受性。可提及的转基因植物的例子是重要的农作物,如谷类农作物(小麦、稻)、玉米、大豆、土豆、棉花、油菜籽油菜和水果植物(水果为苹果、梨、柑橘属水果和葡萄),特别强调的是玉米、大豆、土豆、棉花和油菜籽油菜。特别强调的特性是通过在植物中产生的毒素,特别是通过来自Thuringiensis杆菌的基因物质(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及它们的联合)(下文称作“Bt植物”)在植物中产生的那些增强植物对昆虫的抵御。作为特性也可特别强调的是通过系统获得的抗性(SAR)、Systemin、植物抗毒素、Elicitor以及抗性基因和相应表达的蛋白和毒素使植物对真菌、细菌和病毒抵御的增强。此外,特别强调的特性是植物对某些除草活性化合物,如咪唑啉酮类、磺酰脲类、草甘膦类或膦基麦黄酮(例如“PAT”基因)的增强的耐受性。给予所述的需要的特性的基因也可以在转基因植物中相互联合存在。可提及的“Bt植物”的例子是以商标名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(土豆)出售的玉米品种、棉花品种、大豆品种和土豆品种。可提及的耐受除草剂的植物是以商标名Roundup Ready(耐受草甘膦,例如玉米、棉花、大豆)、Liberty Link(耐受膦基麦黄酮,例如油菜籽油菜)、IMI(耐受咪唑啉酮类)和STS(耐受磺酰脲类,例如玉米)出售的玉米品种、棉花品种、大豆品种。可提及的耐除草剂的植物(以常规方式除草剂耐受育种)包括以商标名Clearfield(例如玉米)出售的品种。当然,这些叙述也适用于具有所述特性或将来还要改良的基因特性的将来开发的植物或将来投放市场的植物品种。
所列的植物可按照本发明以特别有利的方式用本发明式(I)活性化合物或本发明的活性化合物混合物进行处理。上述优选的化合物或混合物的范围也适用于这些植物的处理。特别强调的是用本文中特别提及的化合物或混合物处理植物。
本发明活性化合物不仅对植物害虫、卫生害虫和储藏物品中的害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,例如硬蜱、软蜱、兽疥癣螨、虱状蒲螨、蝇(叮咬和吸食)、寄生性蝇幼虫、虱、毛虱、羽虱和跳蚤。这些寄生虫包括:
虱目,例如,血虱属、颚虱属、虱属、Pthirus spp.、管虱属;
食毛目以及钝角亚目和细角亚目,例如,毛羽虱属、Menoponspp.、巨毛虱属、羽虱属、Werneckiella spp.、Lepikentron spp.、畜虱属、嚼虱属、猫羽虱属;
双翅目以及长角亚目和短角亚目,例如,伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、Lutzomyia spp.、库蠓属、斑虻属、瘤虻属、黄虻属、虻属、麻翅虻属、Philipomyia spp.、蜂虱蝇属.、家蝇属、齿股蝇属、螫蝇属、角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、Wohlfahrtia spp.、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、Lipoptena spp.、蜱蝇属;
蚤目,例如,蚤属、栉首蚤属、印鼠客蚤属、角叶蚤属;
异翅亚目,例如,臭虫属、椎猎蝽属、红腹猎蝽属、全圆蝽属;
蜚蠊目,例如,东方蜚蠊、美洲大蠊、德国小蠊、蜚蠊属;
蜱螨目以及后气门亚目和中气门亚目,例如,锐缘蜱属、纯缘蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、Haemophysalis spp.、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺刺螨属、胸孔螨属、瓦螨属;
辐螨亚目(前气门亚目)和粉螨目(无气门亚目),例如,蜂跗线螨属、姬螫螨属、禽螫厘螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、瘁螨属、耳螨属、疥螨属、痂螨属、疙螨属、胞螨属、皮膜螨属。
例如它们对蜱,例如
Amblyomma hebraeum发育的各个阶段、对寄生的蝇类,例如对
Lucilia cuprina具有突出活性。
本发明式(I)活性化合物也适用于防治侵扰农业家畜的节肢动物,所述农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,例如狗、猫、笼养鸟、水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等)的情况,因此,通过使用本发明的活性化合物可以使畜牧业管理更经济而简便。
应用于兽医领域时,本发明活性化合物可通过已知方法即经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、喂食方法、栓剂等形式给药;非经肠给药,例如通过注射(肌肉注射、皮下注射、静脉注射、腹膜内注射等),植入法给药;经鼻给药;经皮肤给药,例如以浸泡或药浴、喷雾、泼浇、擦、洗刷、撒粉方式给药,也可借助于含有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等给药。
当用于家畜、家禽、宠物等时,可将本发明式(I)活性化合物作为含有1-80重量%的活性化合物的制剂形式(例如粉剂、乳剂、流动剂)直接或100-10,000倍稀释后使用,或用作药浴。
另外,发现本发明化合物还对损坏工业材料的昆虫具有很强的杀虫活性。
作为实例并优选列出下述昆虫,但并不限于此:
鞘翅目昆虫,如
北美家天牛、绿虎天牛(Chlorophorus pilosis)、家具窃蠹、报死材窃蠹、类翼窃蠹、Dendrobium pertinex、松芽枝窃蠹、松产品窃蠹(Priobium carpini)、褐粉蠹、粉蠹(Lyctus africanus)、南方粉蠹、栎粉蠹、粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylonaequale)、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、Bostrychuscapucins、褐异翅长蠹、棘长蠹属、竹竿粉长蠹。
革翅目,例如
蓝黑树蜂、云杉大树蜂、泰加大树蜂、大树蜂(Urocerus augur)
白蚁,例如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁、印巴结构木异白蚁、欧美散白蚁、散白蚁(Reticulitermes santonensis)、散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁、内华达古白蚁、台湾乳白蚁。
缨尾目,例如台湾衣鱼。
本发明意义上的工业材料可以理解为表示无生命材料,例如优选合成材料、粘合剂、胶、纸和板、皮革、木材、木制品和油漆。
木材以及木制品是特别需要优选保护使其免受昆虫侵袭的材料。
可用本发明组合物或含有本发明组合物的混合物保护的木材和木制品可以理解为表示,例如:
建筑用木材、木梁、铁路轨枕、桥梁组件、桥型码头、木制交通工具、箱子、货架、集装箱、电话线杆、木外罩、木窗和木门、胶合板、粗纸板、在房屋建筑或建筑细木工行业中常用的细木工或木制品。
所述活性化合物可直接,或以浓缩形式或常规制剂,如粉剂、颗粒剂、溶液、悬浮剂、乳剂或糊剂方式使用。
上述制剂可以已知方法制备,例如通过将本发明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、抗水剂混合,以及如需要加入催干剂和UV稳定剂以及如需要加入染料和颜料,和其它加工助剂。
用于保护木材和木制品的杀虫组合物或浓缩物中包括0.0001至95重量%,特别是0.001至60重量%浓度的本发明活性化合物。
组合物或浓缩物的使用量是根据昆虫的种类和个体密度以及介质而确定的。最佳施用量各自可在应用时通过系列试验确定。然而基于需保护的材料,通常使用0.0001至20重量%,优选0.001至10重量%的活性化合物是足够的。
适合的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或低挥发性的油性或油类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,如需要可加入乳化剂和/或湿润剂。
优选使用的有机化学溶剂是油性或油类溶剂,其蒸发值大于35以及闪点大于30℃,并优选大于45℃。用作上述低挥发度以及不溶于水的油性和油类溶剂物质是相应的矿物油或它们的芳族馏分,或含有矿物油的溶剂混合物,优选石油溶剂、石油和/或烷基苯。
优选使用沸程为170-220℃的矿物油、沸程为170-220℃的石油溶剂、沸程为250-350℃的锭子油、沸程为160-280℃的石油或芳烃,以及松节油等。
在一个优选实施方案中,使用沸程为180-210℃的液体脂族烃或沸程为180-220℃的芳族和脂族烃的高沸程混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
蒸发值大于35以及闪点大于30℃并优选大于45℃的低挥发度的有机油性或油类溶剂可用易或中挥发度的有机溶剂部分替换,条件是溶剂混合物的蒸发值同样大于35以及闪点大于30℃并优选大于45℃,以及该杀虫-杀螨混合物可溶或可乳化于该溶剂混合物中。
在优选实施方案中,部分有机化学溶剂或溶剂混合物被脂族极性有机化学溶剂或溶剂混合物替代。优选使用含有羟基和/或酯基和/或醚基的脂族有机溶剂,例如乙二醇醚、酯等。
本发明使用的有机化学粘合剂是合成树脂和/或粘合干性油,它们本身已知可用水稀释和/或可溶解或分散或乳化于上述使用的机化学溶剂中,特别是由下列物质组成的或包含下列物质的粘合剂丙烯酸树脂、乙烯基树脂,例如聚乙酸乙烯酯、聚酯类树脂、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、酚醛树脂、烃类树脂,如茚/香豆酮树脂、有机硅树脂、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剂、分散剂或溶液形式使用。沥青或沥青状物质也可用作粘合剂,用量至多为10重量%。还可以使用已知的染料、颜料、防水剂、气味调节剂和抑制剂或防腐剂等。
在本发明组合物或浓缩物中优选包括作为有机化学粘合剂的至少一种醇酸树脂或改性醇酸树脂和/或干性植物油。本发明优选使用含油量大于45重量%,优选50-68重量%的醇酸树脂。
上述粘合剂可全部或部分被固定剂(混合物)或增塑剂(混合物)替代。加入这些添加剂的目的是防止活性化合物的蒸发以及结晶或沉淀。它们优选替代0.01至30%的粘合剂(以使用的粘合剂为100%计)。
增塑剂选自邻苯二甲酸酯类的化学物质,如邻苯二甲酸二丁酯、邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯;磷酸酯类如磷酸三丁酯;己二酸酯,如二-(2-乙基己基)己二酸酯;硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯;油酸酯,如油酸丁酯;甘油醚或高分子量的乙二醇醚;甘油酯和对甲苯磺酸酯。
固定剂在化学上基于聚乙烯烷基醚,如聚乙烯基甲基醚或酮,如二苯甲酮和亚乙基二苯甲酮。
其它适用的溶剂或稀释剂特别是水,任选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使用。
特别有效的木材保护方法是通过大批量的浸渍方法,例如通过真空、双真空或加压方法。
现用组合物可任选还包含其它的杀虫剂和任选还包含一种或多种杀真菌剂。
作为另外的共混组分优选可以是在WO 94/29 268中所述的杀虫剂或杀菌剂。明确将在该文献中所述的化合物作为本申请的一部分。
十分特别优选的共混组分可以是杀虫剂,例如毒死蜱、腈肟磷、Silafluofin、甲体氯氰菊酯、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、Thiacloprid、Methoxyphenoxid和杀虫隆,以及杀菌剂,如氧唑菌、己唑醇、戊环唑、丙环唑、戊唑醇、环唑醇、环戊唑菌、烯菌灵、抑菌灵、对甲抑菌灵、3-碘-丙炔基丁氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
同样,本发明的活性化合物可用于保护经常与海水或盐水接触的各种物品,尤其是船体、滤器、网、船体结构、锚和信号装置免受生物附着。
由于定居性寡毛纲目,如龙介虫科以及甲壳类和Ledamorpha(茗荷儿)类,如各种茗荷属和铠茗荷属,或藤壶亚目(藤壶虫),如藤壶属或指茗荷属的附着增加了船体的摩擦阻力并由于增加了能源消耗以及此外经常滞留干船坞,这样明显增加了运营成本。
此外附着生物还有海藻,例如水云属和仙菜属,特别重要的是定居性软甲亚纲(昆甲类)的附着,该昆甲类包括在蔓足纲(蔓足类甲壳动物)中。
令人惊奇地,现已发现本发明活性化合物本身或与其它活性化合物的组合具有突出的防污(抗植被)作用。
使用本发明活性化合物本身或与其它活性化合物的组合时,可以不使用重金属,如,例如硫化二(三烷基锡)、月桂酸三正丁基锡、氯化三正丁基锡、氧化亚铜、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、聚合钛酸丁酯、苯基-(联吡啶)-三氯化铋、氟化三正丁基锡、亚乙基二硫代氨基甲酸锰、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-氧化物的锌和铜盐、双二甲基二硫代氨基甲酰基亚乙基双硫代氨基甲酸锌、氧化锌、亚乙基双二硫代氨基甲酸亚铜、硫氰酸铜、环烷酸铜和卤化三丁基锡,或显著降低上述化合物浓度。
即用防污漆还可任选包含其它活性化合物,优选杀藻剂、杀菌剂、除草剂、杀软体动物剂或其它防污活性化合物。
下列组分优选用于本发明防污组合物的混合组分:
杀藻剂,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、草藻灭、醋酸三苯基锡、异丙隆、噻唑隆、乙氧氟草醚、灭藻醌和特丁净,
杀菌剂,如
苯并[b]噻吩甲酸环己基酰胺-S,S-二氧化物、抑菌灵、Fluorfolpet、3-碘-2-丙炔基丁基氨基甲酸酯、对甲抑菌灵和唑类,如戊环唑、环唑醇、氧唑菌、己唑醇、环戊唑菌、丙环唑和戊唑醇;
杀软体动物剂,如
醋酸三苯基锡、四聚乙醛、灭虫威、贝螺杀、硫双威和混杀威;
或常用防污活性化合物,如
4,5-二氯-2-辛基-4-异噻唑啉-3-酮、二碘甲基paratryl砜、2-(N,N-二甲基硫代氨基甲酰基硫基)-5-硝基噻唑基、2-吡啶硫醇-1-氧化物的钾、铜、钠和锌盐、吡啶三苯基硼烷、四丁基二锡氧烷、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。
使用的防污组合物中包含浓度为0.001至50重量%,特别是0.01至20重量%的本发明活性化合物。
本发明防污组合物还包括在下述文献例如Ungerer,Chem.Ind.1985,37,730-732和Williams,Antifouling MarineCoatings,Noyes,Park Ridge,1973中公开的常用组分。
除了杀藻、杀菌、杀软体动物活性化合物和本发明的杀虫活性化合物外,防污涂料组合物中还特别包括粘合剂。
公知的粘合剂的实例包括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/醋酸乙烯酯共聚物体系、丁二烯/苯乙烯/丙烯腈橡胶、干性油,如亚麻子油,树脂酯或与焦油或沥青、柏油以及环氧化合物、少量的氯化橡胶、氯化聚丙烯和乙烯基树脂混合形成的改性硬树脂。
涂料中还任选可包含优选不溶于海水的无机颜料、有机颜料或染料。涂料中还可包括如松香类物质,以使活性化合物可控制地释放。此外,涂料中可以包含增塑剂,影响流变性质的改良剂,以及其它常规组分。还可以将本发明化合物或上述混合物加入自抛光防污体系中。
所述活性化合物还适于防治封闭空间,如公寓、厂房、办公室、车厢等空间中发生的有害动物,特别是昆虫、蜘蛛和螨。可将它们本身或与其它活性物质或助剂组合加入用于防治上述害虫的家用杀虫剂产品中使用。它们对敏感和抗性种群以及所有发育阶段都有杀虫活性。这些有害动物包括:
蝎目,例如钳蝎(Buthus occitanus)。
蜱螨目,例如波斯锐缘蜱、翘缘锐缘蜱、苔螨属、鸡皮刺螨、家食甜螨、非洲钝缘蜱、血红扇头蜱、恙螨(Trombicula alfreddugesi)、Neutrombicula autumnalis、屋尘螨、粉尘螨。
蛛形目,例如鸟蛤蛛科、园蛛科。
盲蛛目,例如拟蝎类(Pseudoscorpiones chelifer)、Pseudoscorpiones cheiridium、Opiliones phalangium。
等足目,例如潮虫、鼠妇。
倍足目,例如具斑马陆、山蛩虫属。
唇足目,例如地蜈蚣属。
Zygentoma目,例如栉衣鱼属、台湾衣鱼、Lepismodesinquilinus。
蜚蠊目,例如东方蜚蠊、德国小蠊、小蠊属(Blattellaasahinai)、马得拉蜚蠊、角腹蠊属、木蠊属、澳洲大蠊、美洲大蠊、褐斑大蠊、黑胸大蠊、长须蜚蠊。
跳跃亚目,例如家蟀。
革翅目,例如欧洲球螋。
等翅目,例如木白蚁属、散白蚁属。
啮虫目,例如Lepinatus属、粉啮虫属。
鞘翅目,例如圆皮蠹属、毛皮蠹属、皮蠹属、长头谷蠹、隐跗郭公虫属、蛛甲属、谷蠹、谷象、米象、玉米象、药材甲。
双翅目,例如埃及伊蚊、白纹伊蚊、Aedes taeniorhynchus、按蚊属、红头丽蝇、高额麻虻、致倦库蚊、尖音库蚊、Culex tarsalis、果蝇属、夏厕蝇、家蝇、白蛉属、麻蝇(Sarcophaga carnaria)、蚋属、厩螫蝇、大蚊(Tipula paludosa)。
鳞翅目,例如小蜡螟、蜡螟、印度古斑螟、谷蛾、袋谷蛾、幕谷蛾。
蚤目,例如犬栉首蚤、猫栉首蚤指名亚种、人蚤、穿皮潜蚤、印鼠客蚤。
膜翅目,例如广布弓背蚁、亮毛蚁、黑毛蚁、Lasius umbratus、小家蚁、Paravespula属、铺道蚁。
虱目,例如头虱、体虱、阴虱。
异翅亚目,例如热带臭虫、温带臭虫、长红猎蝽、侵扰锥猎蝽。
在家用杀虫剂领域中应用其本身或与其它合适的活性物质组合,例如与磷酸酯类、氨基甲酸酯类、拟除虫菊酯类、生长调节剂类或其它已知的杀虫剂种类的活性物质组合。
它们可以如下述使用:气溶胶,非增压喷雾剂,例如泵喷雾、喷洒喷雾、烟雾发生器、浓雾、泡沫、凝胶、带有纤维素或聚合物制成的蒸发片的蒸发产品、液体蒸发器、凝胶和薄膜蒸发器、推进式蒸发器、不需能量或被动式蒸发系统、捕蛀虫纸、捕蛾袋和捕虫胶、作为颗粒剂或粉剂、在撒布饵料中或饵料位置。
通过下列实施例说明本发明物质的制备和应用。
制备实施例
方法A
外消旋体分离:式(I)的Δ
1
-吡咯啉
将(+/-)-5-(2,6-二氟苯基)-2-[4′-(三氟甲氧基)-1,1′-联苯基-4-基]-3,4-二氢-2H-吡咯(I-3)(8g)溶于1升正庚烷/异丙醇9∶1(v/v=体积/体积),然后按照高效液相色谱的原理在硅胶相Chiralcel OD[制造商:Daicel(Japan),柱尺寸:500mm×40mm(I.D.),颗粒大小:20μm,流速:40ml/min]进行色谱分离,用正庚烷/异丙醇9∶1(v/v)作为洗脱剂。为了全部分离,每30min各向柱上施加5ml(各相当于40mg外消旋体)。化合物的检测用UV-检测器在254nm波长下进行。在分析测试后合并对映体纯的洗脱级分,减压下最大程度地蒸发,过滤残余物,用正庚烷洗涤并干燥,将由此得到的粗品在硅胶上纯化(洗脱剂∶正己烷/乙酸乙酯,1∶9→1∶4,各为v/v),得到7g(2R)-5-(2,6-二氟苯基)-2-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-3,4-二氢-2H-吡咯(I-3)。
通过方法A得到下列式(I)的光学活性的Δ1-吡咯啉:
方法B:钯-催化的偶联反应
在氮气氛、80℃下搅拌4-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基-三氟甲磺酸酯(I-a-1)(1.01g,2.5mmol)、二(频哪醇合)乙硼烷(Bis(pinacolato)diboron)(0.76g,3.0mmol)、KOAc(0.74g,7.5mmol)、PdCl2[dppf](60mg,0.075mmol)和二甲氧基乙烷(15ml)3.5h。将反应混合物冷却至室温,用水稀释,用乙酸乙酯萃取。有机相经盐水洗涤、硫酸钠干燥、过滤和减压浓缩。剩下的残余物用二氯甲烷处理,加入5g硅酸镁载体(Florisil)并浓缩溶液,粗产品经硅胶色谱纯化(洗脱剂∶环己烷/乙酸乙酯,4∶1v/v),得到0.55g(理论量的57%)(2R)-5-(2,6-二氟苯基)-2-[4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯基]-3,4-二氢-2H-吡咯(I-b-1)。
HPLC:LogP(pH7)=4.47(纯度96.6%)。
旋光值:[α]D=+24.8(c=0.9,MeOH);20℃。
在80℃下搅拌4-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基-三氟甲磺酸酯(I-a-1)(1.01g,2.5mmol)、二(频哪醇合)乙硼烷(0.76g,3.0mmol)、KOAc(0.74g,7.5mmol)、PdCl2[dppf](60mg,0.075mmol)和二甲氧基乙烷(15ml)3h。将反应混合物冷至室温,然后加入4-三氟甲氧基苯基溴苯(III-1)(0.72g,3mmol)、PdCl2[dppf](60mg,0.075mmol)和2M Na2CO3水溶液(7.5ml)并在80℃下继续搅拌16h。将反应混合物冷至室温,用水稀释并用乙酸乙酯萃取。有机相用水洗涤,硫酸钠干燥并过滤,加入硅酸镁载体(4g)并减压浓缩溶液。粗产品经硅胶色谱纯化(洗脱剂∶正己烷/乙酸乙酯,1∶9→1∶4,各为v/v),得到0.61g(理论量的59%)(2R)-5-(2,6-二氟苯基)-2-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-3,4-二氢-2H-吡咯(I-3)。
HPLC:Log P(pH2.3)=4.08(纯度94.4%)
旋光值:[α]D=+33.9(c=0.9,MeOH);20℃
在80℃下搅拌4-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基-三氟甲磺酸酯(I-a-1)(1.01g,2.5mmol)、二(新戊基乙二醇合)乙硼烷(0.68g,3.0mmol)、KOAc(0.74g,7.5mmol)、PdCl2[dppf](60mg,0.075mmol)和N,N-二甲基乙酰胺(15ml)3h。将反应混合物冷至室温,然后加入4-溴苯基三氟甲基砜(III-11)(0.72g,3mmol)、PdCl2[dppf](60mg,0.075mmol)和2M Na2CO3水溶液(7.5ml)并在80℃下继续搅拌16h。将反应混合物冷至室温,用水稀释并用乙酸乙酯萃取。有机相用水洗涤,硫酸钠干燥并过滤,加入硅酸镁载体(4g)并减压浓缩该溶液。粗产品经硅胶色谱纯化(洗脱剂∶正己烷/乙酸乙酯,4∶1,v/v),得到0.60g(理论量的52%)(2R)-5-(2,6-二氟苯基)-2-{4′-[(三氟甲基)-磺酰基]-1,1′-联苯-4-基}-3,4-二氢-2H-吡咯(I-11)。
HPLC:Log P(pH2.3)=3.92(纯度100%)
旋光值:[α]D=+36.0(c=0.35,甲醇);20℃
在80℃下过夜搅拌4-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]苯基-三氟甲磺酸酯(I-a-1)(9.00g,22.2mmol)、4-{[叔丁基(二甲基)甲硅烷基]氧基}苯基硼酸(II-1)(8.40g,33.3mmol)、K2CO3(6.14g,44.4mmol)、Pd[PPH3]4(1.28g,1.1mmol)、二甲氧基乙烷(150ml)和蒸馏水(50ml)。将反应混合物冷至室温,用乙酸乙酯(300ml)处理,有机相用水洗涤,硫酸钠干燥、过滤并减压浓缩,该粗产品经硅胶色谱纯化(洗脱剂∶甲苯/乙酸乙酯,4∶1v/v),得到7.67g(理论量的75%)(2R)-2-(4′-{[叔丁基(二甲基)甲硅烷基]氧基}-1,1′-联苯-4-基)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯(I-8),熔点33℃。
HPLC:Log P(pH2.3)=6.20(纯度93.68%)
得到1.80g(理论量的23%)4′-[(2R)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯-2-基]-1,1′-联苯-4′-醇(I-9),熔点217℃。
HPLC:Log P(pH2.3)=1.93(纯度98.48%)
通过方法B得到下列其它的式(I)的光学活性Δ1-吡咯啉:
方法C
式(VII)内酰胺生成式(V)N-Boc-内酰胺的反应
将(5R)-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮(VII-1)(0.51g,77.9%,约1.23mmol)加到二氯甲烷(10ml)中,加入叔丁氧基羰基酸酐(1.9mmol,0.56g)和二甲基氨基吡啶(0.02g,0.32mmol)并在室温下继续搅拌该混合物过夜,用二氯甲烷(40ml)稀释该混合物,有机相依次用1M HCl、饱和碳酸氢钠水溶液和盐水洗涤,经硫酸镁干燥,过滤并减压浓缩,得到0.42g(理论量的75%)叔丁基-(5R)-2-氧代-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-1-吡咯烷甲酸酯(V-1),其作为粗产品不经进一步纯化用于下一步反应。
HPLC:Log P(pH2.3)=4.32(纯度93.1%)
将(5R)-5-(4-溴苯基)-2-吡咯烷酮(VII-2)(1.38g,5.7mmol)加到二氯甲烷(40ml)中,加入叔丁氧基羰基酸酐(6.9mmol,1.50g)和二甲基氨基吡啶(0.14g,1.14mmol)并在室温下继续搅拌该混合物2天,有机相依次用1M HCl、饱和碳酸氢钠水溶液和盐水洗涤,经硫酸钠干燥,过滤和减压浓缩。粗产品用异丙醇研制并抽滤,得到0.71g(理论量的35%)叔丁基-(2R)-2-(4-溴苯基)-5-氧代-1-吡咯烷甲酸酯(V-2)。
HPLC:Log P(pH2.3)=3.04(纯度96.5%)
类似地合成下列化合物:
式(V)N-Boc-内酰胺生成式(IV)N-Boc-氨基酮的反应
在-78℃、氩气氛下,将1,3-二氟苯(0.29g,2.55mmol)加到THF(30ml)中,向该溶液中先后滴加n-BuLi(1.6M在己烷中,2.55mmol,1.59ml)和四甲基乙二胺(2.55mmol,0.38ml)。在-78℃下继续搅拌20min,然后在该温度下滴加在THF(2ml)中的(V-1)化合物(1.70mmol,0.72g)。过夜搅拌该反应混合物并使其升至室温,然后倒入水(10ml)中,水相用乙酸乙酯(100ml)萃取并用盐水洗涤有机相,经硫酸镁干燥,过滤和减压浓缩,得到0.52g(理论量的30%)叔丁基-(1R)-4-(2,6-二氟苯基)-4-氧代-1-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁基氨基甲酸酯(IV-1),其作为粗产品不经进一步纯化用于下一步反应。
HPLC:Log P(pH 2.3)=5.18(纯度52.9%)
在-78℃、氩气氛下,将1,3-二氟苯(0.31g,2.7mmol)加到THF(20ml)中,向该溶液中先后滴加n-BuLi(1.6M在己烷中,2.7mmol,1.69ml),在-78℃下继续搅拌15min,然后在该温度下滴加在THF(2ml)中的化合物V-2(1.80mmol,0.60g)。过夜搅拌该反应混合物并使其升至室温,然后倒入水(10ml)中,水相用乙酸乙酯(100ml)萃取并用盐水洗涤有机相,经硫酸镁干燥,过滤和减压浓缩,得到0.65g(理论量的60%)叔丁基-(1R)-1-(4-溴苯基)-4-(2,6-二氟苯基)-4-氧代丁基氨基甲酸酯(IV-2),其作为粗产品不经进一步纯化用于下一步反应。
HPLC:Log P(pH2.3)=4.22(纯度75.3%)
类似地合成下列化合物:
式(IV)N-Boc-氨基酮生成式(I)吡咯啉的反应
在0℃下,将化合物(IV-1)(0.10g,0.19mmol)加到二氯甲烷(5ml)中,滴加三氟乙酸(0.14ml,18.7mmol)并在室温下继续搅拌该反应混合物3h,然后浓缩至干,残余物用二氯甲烷处理并用2M NaOH调至pH12。有机相经用水洗涤,硫酸镁干燥,过滤和减压浓缩,得到0.09g(理论量的约100%)(2R)-5-(2,6-二氟苯基)-2-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-3,4-二氢-2H-吡咯(I-3)。
HPLC:Log P(pH2.3)=4.13(纯度90.4%)
旋光值:[α]D=+33.9(c=0.9,MeOH);20℃
对映体过量(ee-值):99.0%
在0℃下,将化合物(IV-2)(0.65g,75.3%)加到二氯甲烷(20ml)中,滴加三氟乙酸(1.08ml,14.0mmol)并在室温继续搅拌3h,然后浓缩至干。残余物用乙酸乙酯处理并用1M NaOH调至pH11。有机相经用水洗涤,硫酸镁干燥,过滤和减压浓缩,粗产品经硅胶色谱纯化(洗脱剂∶环己烷/乙酸乙酯,8∶1v/v),得到0.19g(理论量的53%)(2R)-2-(4-溴苯基)-5-(2,6-二氟苯基)-3,4-二氢-2H-吡咯(I-15)。
HPLC:Log P(pH2.3)=2.74(纯度96.69%)
对映体过量(ee-值):99.9%
类似地合成下列化合物:
方法γ
通过外消旋体分离制备式(VII)的光学活性内酰胺
在室温下通过在手性聚酰胺-硅胶固定相上的液相色谱进行外消旋体的分离,用乙酸乙酯作为洗脱剂并用分光光度计检测。所用的手性相基于单体N-甲基丙烯酰基-L-亮氨酸-d-基酰胺,其经过自由基聚合共价键结合到改性的硅胶上。这类固定相例如描述于EP-A 0 379917中。在上述条件下首先洗脱出右旋的对映体。
分离相:1000g硅胶-CSP;10μm,如上述
柱:450mm×75mm
洗脱剂:乙酸乙酯
流速:100ml/min
UV-检测:254nm
加样:6g外消旋体(=150ml 40g外消旋体在1升乙酸乙酯中的溶液)
如此设定色谱分离条件,使第二对映体的洗脱通过用100%的甲醇的短时梯度加速,并由此可大大缩短总的洗脱时间。
在分析检测后,合并相应的对映体纯的洗脱级分,在减压下尽可能地浓缩,过滤残余物,用正庚烷洗涤并干燥。
式(VII)内酰胺的对映体纯度按下述通过HPLC确定:
柱:CSP类似于制备分离(10μm;250×4.6mm)
洗脱剂∶乙酸乙酯/甲醇25∶1(v/v)
流速:1ml/min
UV-检测:280nm
通过方法γ得到下述式(VII)内酰胺:
方法δ:式(VII)内酰胺的不对称合成
(3S,7aS)-3-苯基-7a-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-四氢吡
咯并[2,1-b][1,3]噁唑-5(6H)-酮(IX-1)
应用分水器加热回流4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酸(VIII-1)(11.00g,32.5mmol)、2(S)-2-氨基-2-苯基乙醇(4.46g,32.5mmol)、4-甲苯磺酸(1.10g,5.8mmol)和甲苯(400ml)3.5h。将该反应混合物冷却,过滤并浓缩。残余物用二异丙基醚研制并抽滤。
产量:5.56g,理论量的39%
HPLC:Log P(pH2.3)=4.55(纯度92.8%)
旋光值:[α]D=+75.8(c=0.9,MeOH);20℃
熔点:104℃
(3S,7aS)-7a-(4-溴苯基)-3-苯基四氢吡咯并[2,1-b][1,3]噁唑-
5(6H)-酮(IX-2)
应用分水器加热回流3-(4-溴苯甲酰基)-丙酸(VIII-2)(18.75g,72.9mmol)、2(S)-2-氨基-2-苯基乙醇(10.0g,72.9mmol)、4-甲苯磺酸(2.47g,13.0mmol)和甲苯(400ml)3.5h。将该反应混合物冷却,过滤和减压浓缩。该粗产品用硅胶色谱纯化(洗脱剂∶环己烷/乙酸乙酯,6∶1v/v)。
产量:15.47g,理论量的55%
HPLC:Log P(pH2.3)=3.36(纯度92.3%)
旋光值:[α]D=+82.0(c=1.0,MeOH);20℃
熔点:111-113℃
(5R)-1-[(1S)-2-羟基-1-苯基乙基]-5-[4′-(三氟甲氧基)-1,1′-联
苯-4-基]-2-吡咯烷酮(X-1)
将化合物(IX-1)(3.81g,8.7mmol)加到二氯甲烷(75ml)中并在-78℃下依次滴加三乙基硅烷(3.37g,29mmol)和TiCl4(1M的CH2Cl2溶液,19.1ml,19mmol)。在-78℃下2h后,在室温下过夜搅拌,将该反应混合物冷至0℃,滴加饱和的氯化铵水溶液(100ml)。有机相用水洗涤、硫酸钠干燥、过滤和减压浓缩,该粗产品不经进一步纯化用于下一步反应。
产量:3.63g(理论量的95%)
HPLC:Log P(pH2.3)=3.80(纯度96.9%)
(5R)-5-(4-溴苯基)-1-[(1S)-2-羟基-1-苯基乙基]-2-吡咯烷酮(X-
2)
将化合物(IX-2)(3.12g,8.7mmol)加到二氯甲烷(75ml)中并在-78℃下依次滴加三乙基硅烷(3.37g,29mmol)和TiCl4(1M的CH2Cl2溶液,19.1ml,19mmol)。在-78℃下2h后,在室温下过夜搅拌,将该反应混合物冷至0℃,滴加饱和的氯化铵水溶液(100ml)。有机相用水洗涤、硫酸钠干燥、过滤和减压浓缩,该粗产品不经进一步纯化用于下一步反应。
产量:3.12g(理论量的约100%)
HPLC:Log P(pH2.3)=2.58(纯度100%)
旋光值:[α]D=+40.0(c=1.0,MeOH);20℃
(5R)-1-[(1S)-2-氯-1-苯基乙基]-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮(XI-1)
将化合物(X-1)(0.44g,1.0mmol)加到THF(10ml)中并滴加亚硫酰氯(0.29g,2.42mmol),继续搅拌该反应混合物1.5h并浓缩。该粗产品不经进一步纯化用于下一步反应。
产量:0.38g(理论量的83%)
HPLC:Log P(pH2.3)=4.78(纯度93.1%)
(5R)-5-(4-溴苯基)-1-[(1S)-2-氯-1-苯基乙基]-2-吡咯烷酮(XI-2)
将化合物(X-2)(2.00g,5.0mmol)加到THF(10ml)中并滴加亚硫酰氯(1.19g,10.0mmol),继续搅拌该反应混合物1.5h并浓缩。
该粗产品不经进一步纯化用于下一步反应。
产量:1.69g(理论量的82%)
HPLC:Log P(pH2.3)=3.61(纯度91.8%)
旋光值:[α]D=+42.0(c=0.85,MeOH);20℃
(5R)-1-(1-苯基乙烯基)-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-
吡咯烷酮(XII-1)
将化合物(XI-1)(0.50g,1.1mmol)加到tBuOH(5ml)中并加入KOtBu(0.26g,2.4mmol)。在60℃下继续搅拌该反应混合物过夜,冷却并浓缩。残余物用乙酸乙酯处理并依次用1M HCl和水洗涤。有机相用硫酸镁干燥,过滤和浓缩。该粗产品不经进一步纯化用于下一步反应。
产量:0.34g(理论量的74%)
HPLC:Log P(pH2.3)=4.35(纯度98.4%)
(5R)-5-(4-溴苯基)-1-(1-苯基乙烯基)-2-吡咯烷酮(XII-2)
将化合物(XI-2)(1.00g,2.6mmol)加到tBuOH(10ml)中并加入KOtBu(0.64g,5.7mmol)。在60℃下继续搅拌该反应混合物过夜,冷却并浓缩。残余物用乙酸乙酯处理并依次用1M HCl和水洗涤。有机相用硫酸镁干燥,过滤和浓缩。该粗产品不经进一步纯化用于下一步反应。
产量:0.67g(理论量的34%)
HPLC:Log P(pH2.3)=3.18(纯度45.75%)
(5R)-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮(VII-1)
将化合物(XII-1)(0.98g,2.3mmol)加到THF(5ml)中并加入1M HCl(5ml)。在60℃下继续搅拌该反应混合物1h,冷却并浓缩。残余物用乙酸乙酯处理(100ml)。有机相依次用饱和的碳酸氢钠水溶液和盐水洗涤,硫酸镁干燥,过滤和浓缩。该粗产品不经进一步纯化用于下一步反应。
产量:0.51g(理论量的74%)
HPLC:Log P(pH2.3)=2.95(纯度77.9%)
对映体过量(ee-值):97.1%(按照用于内酰胺的方法1)
(5R)-5-(4-溴苯基)-2-吡咯烷酮(VII-2)
将化合物(XII-2)(0.57g,1.7mmol)加到THF(3ml)中,加入1M HCl(3ml)并在60℃下继续搅拌该反应混合物1h,将其冷至室温并浓缩,残余物用二氯甲烷(30ml)处理并在0℃下用1N NaOH调至pH 11。有机相用水洗涤,硫酸镁干燥,过滤和浓缩。该粗产品不经进一步纯化用于下一步反应。
产量:0.36g(理论量的84%)
HPLC:Log P(pH2.3)=3.54(纯度95.3%)
旋光值:[α]D=+33.6(c=1.0,MeOH);20℃
对映体过量(ee-值):99.8%(按照用于内酰胺的方法1)
方法ε:式(VII)内酰胺的不对称合成
甲基-4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酸酯(VIII-
a-1)
将4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酸的粗品(25g,含量:65%,GC,甲硅烷基化的,100%-方法)溶于甲醇(50ml)和2,2-二甲氧基丙烷(11.5g,110mmol)的混合物中,与三甲基甲硅烷基氯(0.75g,7mmol)混合并在50℃下搅拌16h。然后浓缩该反应混合物,残余物用甲苯重结晶。
产量:18.2g
HPLC:Log P(pH2.3)=4.01
N-烯丙基-4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酰胺
(XV-1)
将甲基-4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酸酯(VIII-a-1)(18.2g,52mmol)与烯丙基胺(41.6g,730mmol)和氯化铵(1.8g,33mmol)混合并加热回流6h。为了后处理,将该混合物加到冰冷却的HCl(2M)中,用乙酸乙酯萃取,合并的有机相经干燥(Na2SO4)和浓缩。粗产品(17.7g,含量:84.5%,HPLC,100%-方法)用甲苯重结晶。
产量:8.6g
HPLC:Log P(pH2.3)=3.34,3.42
(4S)-N-烯丙基-4-羟基-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酰
胺(XVI-1)
在氩气氛下,在已加热干燥过的Schlenk烧瓶中,将无水N-烯丙基-4-氧代-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酰胺(XV-1)(2.26g,6mmol)溶于无水THF(40ml)中并在0℃下与(3aR)-1-甲基-3,3,6-三苯基四氢-3H-吡咯并[1,2-c][1,3,2]氧杂氮杂硼杂环戊烯(600μl,1M于甲苯中)混合。在0℃下、30min,向该溶液中滴加BH3*SMe2-配合物(7.1ml,0.59M)。在0℃下搅拌该混合物1h,撤去冰浴后,在室温下继续搅拌6h。小心地加入MeOH(10ml)后浓缩该混合物,残余物通过硅胶60过滤进行纯化(洗脱剂∶CH3OH/CH2Cl2,10∶1)。
产量:1.24g
HPLC:Log P(pH2.3)=2.99
对映体过量(ee-值):87%(GC-方法)
(5R)-1-烯丙基-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮
(XVII-1)
在氩气氛下,在已加热干燥过的Schlenk烧瓶中,将KOtBu(0.64g,5.7mmol)悬浮于THF(5ml,无水)中。在0℃下向其中滴加(4S)-N-烯丙基-4-羟基-4-[4′-(三氟甲氧基)-1,1′-联苯-4-基]丁酰胺(XVI-1)(0.99g,2.6mmol)的THF(8ml,无水)溶液。在0℃下搅拌该反应混合物1h,然后在20min内与甲苯磺酰氯(0.52g,2.7mmol)THF(5ml,无水)溶液混合。在0℃下搅拌该混合物2h并在室温下搅拌16h。为了后处理,将该混合物与水混合,用HCl调至pH5并用乙酸乙酯萃取。合并的有机相经干燥(Na2SO4)和浓缩,残余物(0.85g,含量:81%,HPLC,100%-方法)用闪式色谱进一步纯化(洗脱剂∶乙酸乙酯/石油醚(40/60),1∶1)。
产量:0.55g
HPLC:Log P(pH2.3)=3.88
对映体过量(ee-值):85%(GC-方法)
(5R)-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮(VII-1)
在氩气氛下,将(5R)-1-烯丙基-5-[4′-(三氟甲氧基)-1,1′-联苯-4-基]-2-吡咯烷酮(XVII-1)(0.41g,1.14mmol)与Pd[PPh3]4(131.7mg,0.114mmol)和对甲苯磺酸水合物(0.52g,2.74mmol)加到Schlenk烧瓶中,并与THF(2ml,脱气)以及1ml H2O混合。将该黄色溶液加热回流3h。为了后处理,将其冷至室温并用NaHCO3溶液稀释并与乙酸乙酯混合,经硅藻土过滤,干燥(Na2SO4)合并的有机相并减压浓缩。
产量:0.5g(理论量的89%)
HPLC:Log P(pH2.3)=3.00
对映体过量(ee-值):85%(按照用于内酰胺的方法2)
将经色谱纯化的该内酰胺样品用石油醚(40/60)/甲苯重结晶。
熔点:164℃
HPLC:99%
对映体过量(ee-值):99%(按照用于内酰胺的方法2)
上述表和实施例中给出的logP-值的测定按照EEC-说明79/831附件V.A8通过HPLC(高效液相色谱)在反相柱(C18)上进行的,温度:43℃。
所述测定在pH2.3的酸性范围内用0.1%磷酸和乙腈作为洗脱剂;线性梯度从10%乙腈到90%乙腈。
校正用直链的、其logP-值已知的链烷-2-酮(具有3-16个碳原子)进行(logP-值的测定按照保留时间通过两个连续的链烷酮之间的线性内插)。
λmax值根据200nm-400nm的UV-光谱由色谱信号的最大值得到。
式(I)吡咯啉的对映体纯度通过分析HPLC在下述条件下测定:
分离相:Chiralcel OD(Daicel,Japan);5μm
柱:250mm×4.6mm(I.D.)
洗脱剂∶正庚烷/2-丙醇10∶1
流速:1ml/min
UV-检测:254nm
式(VII)内酰胺的对映体纯度通过分析HPLC在下述条件下测定(方法1):
分离相:硅胶-CSP;10μm
柱:250mm×4.6mm(I.D.)
洗脱剂∶乙酸乙酯/甲醇25∶1(v/v)
流速:1ml/min
UV-检测:280nm
式(VII)内酰胺的对映体纯度通过分析HPLC在下述条件下测定(方法2):
分离相:Chiralcel OD-H(Daicel,Japan);5μm
柱:250mm×4.6mm(I.D.)
洗脱剂∶正庚烷/2-丙醇19∶1(v/v)
流速:0.5ml/min
UV-检测:220nm
式(XVI)丁酰胺和式(XVII)吡咯烷酮的对映体纯度通过分析GC在下述条件下测定:
分离相:Hydrodex-β-6TBDM
柱:25m×0.25mm(I.D.)
载气:氦气
压力:120kPa
进样温度:220℃
检测器:FID
温度程序:13min 120℃,1℃/min直至220℃
应用实施例
实施例A
棉铃虫(Heliothis armigera)试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物配剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀该释浓缩物至所需浓度。
将大豆嫩枝(大豆)通过浸入所需浓度的活性化合物配剂中进行处理,并在大豆页仍然潮湿时放上棉铃虫的毛虫。
在希望的时间后确定以%表示的杀死率。对此100%表示所有毛虫都被杀死;0%表示没有毛虫被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表A
植物害虫
棉铃虫-试验
实施例B
烟芽夜蛾(Heliothis virescens)试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物配剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将大豆嫩枝大豆通过浸入所需浓度的活性化合物配剂中进行处理,并在大豆页仍然潮湿时放上烟芽夜蛾的毛虫。
在希望的时间后确定以%表示的杀死率。对此100%表示所有毛虫都被杀死;0%表示没有毛虫被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表B
植物害虫
烟芽夜蛾试验
实施例C
菜娥试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释该浓缩物至所需浓度。
通过浸入到期望浓度的活性化合物配剂中来处理甘蓝叶(Brassica oleracea),并在菜页仍然潮湿时放上甘蓝蠹(小菜娥(plutella xylostella))的毛虫。
在规定时间后测定以%表示的杀死率。对此100%表示杀死了所有毛虫;0%表示没有毛虫被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表C
植物害虫
菜娥-试验
实施例D
甜菜夜娥(Spodoptera exigua)-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物配剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释该浓缩物至所需浓度。
通过浸入到期望浓度的活性化合物配剂中来处理甘蓝叶(Brassica oleracea),并在菜页仍然潮湿时放上覃蝇(甜菜夜娥)的毛虫。
在规定时间后测定以%表示的杀死率。对此100%表示杀死了所有毛虫;0%表示没有毛虫被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表D
植物害虫
甜菜夜娥-试验
实施例E
草地贪夜娥(Spodoptera frugiperda)-试验
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释该浓缩物至所需浓度。
通过浸入到期望浓度的活性化合物配剂中来处理甘蓝叶(Brassica oleracea),并在菜页仍然潮湿时放上覃蝇(草地贪夜娥)的毛虫。
在规定时间后测定以%表示的杀死率。对此100%表示杀死了所有毛虫;0%表示没有毛虫被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表E
植物害虫
草地贪夜娥-试验
实施例F
红叶螨-试验(OP-抗性/浸渍处理)
溶剂:30重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释该浓缩物至所需浓度。
将被所述蜘蛛螨(棉叶螨(Tetranychus urticae))的所有阶段严重侵袭的豆科植物(Phaseolus vulgaris)浸入希望浓度的活性化合物配剂中。
在规定时间后测定以%表示的杀死率。对此100%表示杀死了所有蜘蛛螨;0%表示没有蜘蛛螨被杀死。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表F
植物害螨
红叶螨-试验(OP-抗性/浸入处理)
实施例G
黄瓜条叶甲(Diabrotica balteata)-试验(土壤中的幼虫)
临界浓度试验/土壤昆虫-处理转基因植物
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含乳化剂的水稀释该浓缩物至所需浓度。
将所述活性化合物配剂浇到土壤上。对此该配剂中活性化合物的浓度实际不起作用,起决定作用的只是每单位体积的土壤中活性化合物的重量,该量用ppm(mg/l)表示。将所述土壤装到0.25l的盆中并在20℃保存。
在配制完成后尽快向各盆中放入5粒预发芽的YIELDGUARD(Monsanto Comp.,USA的商标)种的玉米粒。两天后向处理过的土壤中放入相应的测试昆虫。再过7天后通过计数露出土表的玉米苗确定活性化合物的活性程度(1棵植物=20%活性)。
实施例H
烟芽夜蛾(Heliothis virescens)试验(处理转基因植物)
溶剂:7重量份二甲基甲酰胺
乳化剂:1重量份烷基芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
将各种Rundup Ready(Monsanto Comp.,USA的商标)的大豆嫩枝(大豆)通过浸入所需浓度的活性化合物配剂中进行处理,并在大豆页仍然潮湿时放上烟夜蛾烟芽夜蛾。
在规定时间后测定以%表示的杀死率。对此100%表示杀死了所有毛虫;0%表示没有毛虫被杀死。
实施例I
Amblyomma hebraeum(EH)(多宿主的蜱若虫/浸入法)
测试动物:Amblyomma hebraeum的幼(gesogene)若虫
溶剂:二甲基亚砜
将20mg活性化合物溶于1ml二甲基亚砜中,在各种情况下,用水稀释该活性化合物溶液至希望的浓度以制备适合目的的配剂。
将10只完全自身吸吮的若虫浸入待测试活性化合物配剂中1min,将动物转移至放有滤纸片的玻璃盘上(Φ9.5cm)并盖上盖。在空调室中保存4周后确定蜕皮率。
对此,100%表示没有动物正常蜕皮;0%表示所有动物都蜕皮了。
活性化合物、活性化合物的浓度以及试验结果列于下表中。
表I
Amglyomma hebraeum (EH)
(多宿主的蜱若虫/浸入法)
实施例K
Amblyomma hebraeum(EH)(多宿主的蜱若虫/浸入法,ED50-测定)
测试动物:Amblyomma hebraeum的幼若虫
溶剂:二甲基亚砜
将20mg活性化合物溶于1ml二甲基亚砜中,在各种情况下,用水稀释该活性化合物溶液至希望的浓度以制备适合目的的配剂。
为了测定ED50,用1000、300、100、30、10、3、1、0.3、0.1、0.03、0.01ppm的浓度系列测定剂量作用曲线。
将10只完全自身吸吮的若虫浸入待测试活性化合物配剂中1min,将动物转移至放有滤纸片的玻璃盘上(Φ9.5cm)并盖上盖。在空调室中保存4周后确定蜕皮率。
对此,100%表示没有动物正常蜕皮;0%表示所有动物都蜕皮了。
数据通过用XLfit(ID Business Solutions Ltd.)进行4-参数增加曲线拟合来计算。如果在1000ppm下没有达到50%的死亡率,那么ED50就是不能测定的。
活性化合物以及试验结果列于下表中。
表K
Amglyomma hebraeum(EH)
ED50-测定(多宿主的蜱若虫/浸入法)
Claims (21)
1.式(I)的光学活性Δ1-吡咯啉
其中
*表示具有(R)构型的手性碳原子,
m表示0、1、2、3或4,
R1表示卤素或甲基,
R2表示氢或卤素,
R3表示氢、卤素、羟基、烷基、链烯基、炔基、卤代烷基、卤代链烯基、烷氧基、-S(O)oR6、-OSO2R6、二烷氧基甲硼烷、-B(OH)2或表示任选被列于W1的基团一或多取代的苯基,
R4表示卤素、烷基、烷氧基、卤代烷基、卤代烷氧基或-S(O)oR6,
W1表示氰基、卤素、羟基、烷基、卤代烷基、链烯基、卤代链烯基、烷氧基、卤代烷氧基、链烯基氧基、卤代链烯基氧基、烷氧基羰基、三烷基甲硅烷基、三烷基甲硅烷基氧基、-CONH2、-NR7R8、-S(O)oR6或-SO2NR7R8,
o表示0、1或2,
R6表示氢、烷基或卤代烷基,
R7和R8各自独立表示氢、烷基、卤代烷基或一起表示亚烷基或烷氧基亚烷基。
2.按照权利要求1的式(I)的光学活性Δ1-吡咯啉,其中
m表示0、1、2或3,
R1表示氟、氯、溴或甲基,
R2表示氢、氟、氯或溴,
R3表示氢、氟、氯、溴、碘、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-卤代烷基、C2-C6-卤代链烯基、C1-C6-烷氧基、-S(O)oR6、-OSO2R6、二(C4-C8-烷氧基)甲硼烷、-B(OH)2或表示任选被列于W1的基团一或多取代的苯基,
R4表示卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基或-S(O)oR6,
W1表示氰基、卤素、羟基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C6-卤代链烯基氧基、C1-C6-烷氧基羰基、三(C1-C4-烷基)甲硅烷基、三(C1-C4-烷基)甲硅烷基氧基、-S(O)oR6或-SO2NR7R8,
o表示0、1或2,
R6表示氢、C1-C6-烷基或C1-C6-卤代烷基,
R7和R8相互独立表示氢、C1-C6-烷基、C1-C6-卤代烷基或一起表示C2-C6-亚烷基或C1-C4-烷氧基-C1-C4-亚烷基(例如吗啉)。
3.按照权利要求1的式(I)的光学活性Δ1-吡咯啉,其中
m表示0、1或2,
R1表示氟、氯或甲基,
R2表示氢、氟或氯,
R3表示氢、氟、氯、溴、羟基、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基;表示各自被氟或氯取代的C1-C6-烷基或C2-C6-链烯基;表示-S(O)oR6、-OSO2R6、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、-B(OH)2或表示任选被列于W1的基团一至三取代的苯基,
R4表示氟、氯、溴、C1-C6-烷基、C1-C6-烷氧基,各自被氟或氯取代的C1-C6-烷基或C1-C6-烷氧基或表示-S(O)oR6,
W1表示氰基、氟、氯、溴、碘、羟基、C1-C4-烷基、C1-C4-烷氧基,各自被氟或氯取代的C1-C4-烷基、C1-C4-烷氧基、C2-C6-链烯基氧基,表示C1-C4-烷氧基羰基、-OSi(Me2)t-Bu、-S(O)oR6或-SO2NR7R8,
o表示0、1或2,
R6表示氢、C1-C6-烷基或表示被氟或氯取代的C1-C4-烷基,
R7和R8相互独立表示氢、C1-C6-烷基、被氟或氯取代的C1-C6-烷基,或一起表示C4-C5-亚烷基。
4.按照权利要求1的式(I)的光学活性Δ1-吡咯啉,其中
m表示0、1或2,
R1表示氟、氯或甲基,
R2表示氢、氟或氯,
R3表示氢、氯、溴、羟基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-丙烯基、丁烯基、炔丙基、丁炔基、甲氧基、乙氧基、正丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、-SO2CF3、-SO2(CF2)3CF3、-OSO2CF3、-OSO2(CF2)3CF3、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,5,5-四甲基-1,3,2-二氧代硼杂环戊烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、-B(OH)2或表示被氟或氯取代的C1-C4-烷基或表示任选被列于W1的基团一至三取代的苯基,
R3此外表示异丙氧基,
R4表示氟、氯、溴、甲基、乙基、甲氧基、乙氧基、三氟甲基、二氟甲氧基、三氟甲氧基或-SO2CF3,
W1表示氰基、氟、氯、溴、羟基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、正丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基、二氟甲氧基、-CF3、-CHF2、-CClF2,-CF2CHFCl、-CF2CH2F、-CF2CCl3、-CH2CF3、-CF2CHFCF3、-CH2CF2H、-CH2CF2CF3、-CF2CF2H、-CF2CHFCF3、-OCF2CF2H、-OCF=CF2、-SCF3、-SOCF3、-SO2CF3、-SCHF2、-SOCHF2、-SO2CHF2、-OSi(Me2)t-Bu、-SO2NMe2或-CO2Et,
W1此外表示异丙氧基。
5.制备权利要求1的式(I)化合物的方法, 其特征在于
A)将式(I-rac)的外消旋化合物
其中
R1、R2、R3、R4和m具有权利要求1中给出的含义,
在手性硅胶固定相上,在洗脱剂或洗脱剂混合物作为液相存在下色谱分离,
或
B)(i)式(I-a)化合物
其中R1、R2、R4和m具有权利要求1中给出的含义,
和X1表示Cl、Br、I、-OSO2CF3、-OSO2(CF2)3CF3,
与式(II)的金属有机化合物
A-M (II)
其中
A表示任选被列于W1的基团一或多取代的苯基,
其中W1具有权利要求1中给出的含义,
M表示-B(OH)2、Sn(nBu)3或ZnCl,
M此外表示MgCl,
在催化剂存在下,任选在酸结合剂存在下并且任选在稀释剂存在下反应,
或
(ii)式(I-b)的化合物
其中R1、R2、R4和m具有权利要求1中给出的含义,
X2表示-B(OH)2、(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷)-2-基、(5,5-二甲基-1,3,2-二氧杂硼杂环己烷)-2-基、(4,4,6-三甲基-1,3,2-二氧杂硼杂环己烷)-2-基、1,3,2-苯并二氧杂硼杂环戊烯-2-基、Sn(nBu)3或ZnCl,
与式(III)的芳香化合物
T-A (III)
其中
A表示任选被列于W1的基团一或多取代的苯基,
其中W1具有权利要求1中给出的含义,和
T表示Cl、Br、I、-OSO2CF3、-OSO2(CF2)3CF3,
在催化剂存在下,任选在酸结合剂存在下并且任选在稀释剂存在下反应,
或
(iii)式(I-a)的化合物
其中
R1、R2、R4和m具有权利要求1中给出的含义,和
X1具有上述含义,
与式(III)的芳香化合物
T-A (III)
其中
A和T具有上述含义,
在催化剂存在下,在4,4,4′,4′,5,5,5′,5′-八甲基-2,2′-二-1,3,2-二氧杂硼杂环戊烷或在5,5,5′,5′-四甲基-2,2′-二-1,3,2-二氧杂硼杂环己烷或在4,4,4′,4′,6,6′-六甲基-2,2′-二-1,3,2-二氧杂硼杂环己烷或在2,2′-二-1,3,2-苯并二氧杂硼杂环戊烯存在下和任选地在酸结合剂存在下和任选地在稀释剂存在下进行串联反应,
或
C)式(IV)的光学活性的Boc-保护的氨基酮
其中
R1、R2、R3、R4和m具有权利要求1中给出的含义,
通过用路易斯酸或质子酸处理脱保护并且使就地生成的胺在酸存在下环合。
7.按照权利要求1-4任一项的光学活性Δ1-吡咯啉,其特征在于式(I-h)、(I-i)、(I-j)、(I-k)和(I-l)
其中在各种情况下
W1具有权利要求1-3之一中给出的含义。
8.按照权利要求7的光学活性Δ1-吡咯啉,其特征在于式(I-h)、(I-i)、(I-j)、(I-k)和(I-l)
其中在各种情况下
W1表示氰基、氟、氯、溴、羟基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、三氟甲氧基、二氟甲氧基、-CF3、-CHF2、-CClF2、-CF2CHFCl、-CF2CH2F、-CF2CCl3、-CH2CF3、-CF2CHFCF3、-CH2CF2H、-CH2CF2CF3、-CF2CF2H、-CF2CHFCF3、-OCF2CF2H、-OCF=CF2、-SCF3、-SOCF3、-SO2CF3、-SCHF2、-SOCHF2、-SO2CHF2、-OSi(Me2)t-Bu、-SO2NMe2或-CO2Et。
10.按照权利要求1的光学活性Δ1-吡咯啉,其特征在于下述结构式
12.式(IV)的光学活性氨基酮
其中R1、R2、R3、R4和m具有权利要求1中给出的含义。
15.权利要求14的光学活性内酰胺,其特征在于下述结构式
16.权利要求14的光学活性内酰胺,其特征在于下述结构式
17.害虫防治剂,其特征在于含有至少一种权利要求1的式(I)化合物和增量剂和/或表面活性物质。
18.权利要求1的式(I)化合物用于防治害虫的用途。
19.防治害虫的方法,其特征在于将权利要求1的式(I)化合物作用于害虫和/或其栖息地。
20.制备防治害虫的组合物的方法,其特征在于将权利要求1的式(I)化合物与增量剂和/或表面活性物质混合。
21.权利要求1的式(I)化合物用于制备防治害虫的组合物的用途。
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DE10047110.2 | 2000-09-22 | ||
DE10047110A DE10047110A1 (de) | 2000-09-22 | 2000-09-22 | Optisch aktive 2,5-Bisaryl-DELTA·1·-Pyrroline |
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CN (1) | CN1630634A (zh) |
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CA (1) | CA2422958A1 (zh) |
DE (1) | DE10047110A1 (zh) |
EG (1) | EG23084A (zh) |
MX (1) | MXPA03002364A (zh) |
NZ (1) | NZ524813A (zh) |
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DE10154517A1 (de) * | 2001-11-07 | 2003-05-15 | Bayer Cropscience Ag | DELTA·1·-Pyrroline |
DE10243939A1 (de) * | 2002-09-24 | 2004-04-01 | Bayer Cropscience Ag | Pyrroline |
US7439280B2 (en) * | 2004-04-06 | 2008-10-21 | Basf Corporation | Lignocellulosic composite material and method for preparing the same |
WO2013000572A1 (de) * | 2011-06-30 | 2013-01-03 | 2LUTION GmbH | Mittel zur bekämpfung von parasiten an tieren |
US8664756B2 (en) | 2012-07-24 | 2014-03-04 | Medtronic, Inc. | Reconstituted wafer package with high voltage discrete active dice and integrated field plate for high temperature leakage current stability |
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US5274167A (en) * | 1989-01-26 | 1993-12-28 | Bayer Aktiengesellschaft | Polymeriable optically active (meth) acrylic acid derivatives |
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BR0114062A (pt) | 2003-07-01 |
WO2002024643A1 (de) | 2002-03-28 |
EG23084A (en) | 2004-03-31 |
US20090012144A1 (en) | 2009-01-08 |
US7419936B2 (en) | 2008-09-02 |
EP1322607A1 (de) | 2003-07-02 |
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JP2004509166A (ja) | 2004-03-25 |
AU1389702A (en) | 2002-04-02 |
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US20040059129A1 (en) | 2004-03-25 |
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DE10047110A1 (de) | 2002-04-18 |
TWI306853B (en) | 2009-03-01 |
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