CN1080258C - 用作农药的1-h-3-芳基-吡咯烷-2,4-二酮衍生物 - Google Patents
用作农药的1-h-3-芳基-吡咯烷-2,4-二酮衍生物 Download PDFInfo
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- CN1080258C CN1080258C CN95191816A CN95191816A CN1080258C CN 1080258 C CN1080258 C CN 1080258C CN 95191816 A CN95191816 A CN 95191816A CN 95191816 A CN95191816 A CN 95191816A CN 1080258 C CN1080258 C CN 1080258C
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- Prior art keywords
- formula
- alkyl
- chloro
- aryl
- tetramethyleneimine
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- -1 methoxyl group Chemical group 0.000 claims description 83
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 32
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- 239000001301 oxygen Substances 0.000 claims description 29
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- 239000011737 fluorine Substances 0.000 claims description 27
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 13
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- 229910052794 bromium Inorganic materials 0.000 description 26
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
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- 241000500437 Plutella xylostella Species 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 235000015320 potassium carbonate Nutrition 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000017550 sodium carbonate Nutrition 0.000 description 7
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- 241001124076 Aphididae Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 125000004429 atom Chemical group 0.000 description 6
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- 229960000310 isoleucine Drugs 0.000 description 6
- 229910021645 metal ion Inorganic materials 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
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- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- ITKAIUGKVKDENI-UHFFFAOYSA-N pyrimidifen Chemical compound CC1=C(C)C(CCOCC)=CC=C1OCCNC1=NC=NC(CC)=C1Cl ITKAIUGKVKDENI-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 210000004894 snout Anatomy 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
- 239000010409 thin film Substances 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 229940074152 thuringiensin Drugs 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZBOGUDPFEVIZIQ-UHFFFAOYSA-N toluene;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC=C1 ZBOGUDPFEVIZIQ-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
- 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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D491/10—Spiro-condensed systems
-
- 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
- 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
- A01N43/38—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 condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N47/06—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 containing —O—CO—O— groups; Thio analogues thereof
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/36—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C255/00—Carboxylic acid nitriles
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- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
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- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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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
- C07D207/30—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
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Abstract
本发明涉及式(I)的新1-H-3-芳基-吡咯烷-2,4-二酮衍生物、它们的制备方法及其中间体。式(I)的化合物作为农药使用。
其中
A、B、G、X、Y和Z具有说明书中给出的定义。
Description
本发明涉及新的1-H-3-芳基-吡咯烷-2,4-二酮衍生物、它们的多种制备方法和它们作为农药,特别是杀虫剂和杀螨剂的应用。
3-酰基-吡咯烷-2,4-二酮过去曾被描述具有药物特性(S.Suzuki et al.Chem.Pharm.Bull.15. 1120(1967))。并且R.Schmierer和H.Mildenberger(Liebigs Ann.Chem.1985 1095)已合成出N-苯基吡咯烷-2,4-二酮。但这些化合物的生物活性却未被描述。
EP-A 0262399和GB-A 2266888公开了类似结构的化合物(3-芳基-吡咯烷-2,4-二酮),但没有公开它们具有除草、杀虫或杀螨作用的内容。未被取代的二环3-芳基-吡咯烷-2,4-二酮衍生物(EP-A 355599和EP 415211)和取代的单环3-芳基-吡咯烷-2,4-二酮衍生物(EP A 377893和EP442077)是已知的,并且具有除草、杀虫或杀蜗作用。
此外已知的物质是多环3-芳基-吡咯烷-2,4-二酮衍生物(EP442073)和1-H-3-芳基-吡咯烷-二酮衍生物(EP456063和EP521334)。
现在已发现新的取代的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其式如式(I)所示:其中
A代表氢、各自任选被卤素取代的烷基、烯基、烷氧基烷基、多烷氧基烷基、烷硫基烷基、任选被至少一个杂原子间隔的环烷基或各自任选被卤素、烷基、卤代烷基、烷氧基、硝基取代的芳基、芳基烷基或杂芳基,
B代表氢、烷基或烷氧基烷基,或
A和B与和它们相连的碳原子一起代表饱和或不饱和并且任选被至少一个杂原子间隔的未取代或取代的环;
X代表卤素或烷氧基;
Y代表氢、卤素或烷氧基;
Z代表氢、卤素或烷氧基;
E代表金属离子等价物或铵离子;
L和M各自代表氧或硫;
R1代表各自任选被卤素取代的烷基、烯基、烷氧基烷基、烷硫基烷基、多烷氧基烷基或环烷基,它可为杂原子间隔,或代表任选取代的苯基,各自任选取代的苯烷基、杂芳基、苯氧基烷基或杂芳氧基烷基;
R2代表各自任选被卤素取代的烷基、烯基、烷氧基烷基、多烷氧基烷基或各自任选取代的环烷基、苯基或苄基;
R3、R4和R5各自独立地代表各自任选被卤素取代的烷基、烷氧基、烷基氨基、二烷基氨基、烷硫基、烯硫基、环烷基硫基或各自任选取代的苯基、苯氧基或苯硫基;
R6和R7各自独立地代表氢、各自任选被卤素取代的烷基、环烷基、烯基、烷氧基、烷氧基烷基、任选取代的苯基、任选取代的苄基、或者与和它们连接的N原子一起代表任选被氧或硫间隔的环,
但X和Y,或X和Z不同时为卤素。
其中
A、B、E、L、M、X、Y、Z、R1、R2、R3、R4、R5、R6和R7具有前面提到的定义。
由于一个或多个手性中心的存在,所得式(Ia)-(Ig)的化合物的形式一般为立体异构体的混合物,它们在适宜时可用常规方法分离。它们不仅可以其非对映体混合物的形式进行使用,而且也可以纯非对映体或对映体形式进行使用。为简单起见,下面将始终提到式(Ia)至(Ig)的化合物,但这既指纯化合物也指含有不同比例的异构体、对映体和立体异构化合物的混合物。
另外还发现,式(I)的新的取代的1-H-3-芳基-吡咯烷-2,4-二酮衍生物可通过下述方法之一制备:(A)为制备式(Ia)的1-H-3-芳基-吡咯烷-2,4-二酮或它们的烯醇,其中
其中
A、B、X、Y和Z具有前面提到的定义,R8代表烷基;或者β)在制备式(Ia-a)的1-H-3-芳基-吡咯烷-2,4-二酮或它们的烯醇时,
其中
A、B、X和Z具有前面提到的定义,和
Y1代表-OR8,其中R8代表烷基;
在稀释剂存在下,并且在碱存在下使式(IIa)的N-酰基氨基酸酯经历分子内缩合反应,
其中
A、B、X和Z具有前面提到的定义,
Y2代表氟,和
R8代表烷基,优选C1-C8-烷基,或者(B)为制备式(Ib)的化合物,
其中
A、B、X、Y、Z和R1具有前面提到的定义,使式(Ia)的化合物
其中
其中
R1具有前面提到的定义,和
Hal代表卤素,特别是氯或溴,或者β)适宜时在稀释剂存在下,并且适宜时在酸结合剂存在下与通式(IV)的羧酸酐反应,
R1-CO-O-CO-R1 (IV)
其中
其中
A、B、X、Y、Z和R2具有前面提到的定义,和
其中
A、B、X、Y和Z具有前面提到的定义,适宜时在稀释剂存在下,并且适宜时在酸结合剂的存在下与式(V)的氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (V)
其中
其中
A、B、R2、X、Y和Z具有前面提到的定义,和
其中
A、B、X、Y和Z具有前面提到的定义,α) 适宜时在稀释剂存在下,并且适宜时在酸结合剂存在下与通式(VI)
的氯一硫代甲酸酯或氯二硫代甲酸酯反应,
其中
M和R2具有前面提到的定义;或β)与二硫化碳反应,并且随后与式(VII)的烷基卤化物反应,
R2-Hal (VII)
其中
R2具有前面提到的定义,和
其中
A、B、X、Y、Z和R3具有前面提到的的定义,使式(Ia)的化合物
其中
A、B、X、Y和Z具有前面提到的定义,适宜时在稀释剂的存在下,并且适宜时在酸结合剂的存在下与通式(VIII)的磺酰氯反应;
R3-SO2-Cl (VIII)
其中
其中
A、B、L、X、Y、Z、R4和R5具有前面提到的定义,使式(Ia)的1-H-3-芳基-吡咯烷-2,4-二酮或它们的烯醇
其中
A、B、X、Y和Z具有前面提到的定义,与通式(IX)的磷化合物反应;
其中
L、R4和R5具有前面提到的定义,和
其中
A、B、X、Y和Z具有前面提到的定义,和
E代表金属离子等价物或铵离子,使式(Ia)的化合物
其中
A、B、X、Y和Z具有前面给出的定义,适宜时在稀释剂存在下与通式(X)和(XI)的金属化合物或胺反应;
其中
Me代表一价或二价金属离子,
t代表数字I或2,和
R9、R10和R11各自独立地代表氢和/或烷基。(H)另外还发现,为制备式(Ig)的化合物,
其中
A、B、L、X、Y、Z、R6和R7具有前面提到的定义,使式(Ia)的化合物
其中
A、B、X、Y和Z具有前面给出的定义,α) 适宜时在稀释剂的存在下,并且适宜时在催化剂存在下与通式(XII)
的异氰酸酯或异硫氰酸酯反应,
R6-N=C=L (XII)
其中
其中
L、R6和R7具有前面提到的定义。
另外还发现式(I)的新的1-H-3-芳基-吡咯烷-2,4-二酮衍生物表现出显著的杀虫和杀螨活性。此外,式(I)的化合物具有除草剂和杀菌剂的辅助作用。
下列定义适用于本申请的通式:
A优选代表氢、各自任选被卤素取代的C1-C12-烷基、C3-C8-烯基、C1-C10-烷氧基-C2-C8-烷基、C1-C8-多烷氧基-C2-C8-烷基、C1-C10-烷硫基-C2-C6-烷基、任选被氧和/或硫间隔的具有3至8个环原子的环烷基或各自任选被卤素、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基和/或硝基取代的芳基、杂芳基或芳基-C1-C6-烷基。
B优选代表氢、C1-C12-烷基或C1-C8-烷氧基烷基,或
A、B和与它们相连的碳原子优选代表饱和或不饱和C3-C10-螺环,所述螺环任选被烷基、环烷基、卤代烷基、烷氧基、硫代烷基、卤素或苯基单取代或多取代并且任选被氧或硫间隔,或
A、B和与它们相连的碳原子优选代表C3-C6-螺环,所述螺环被任选为一个或二个氧和/或硫原子所间隔的亚烷二基(alkylenediyl)、或被亚烷二氧基或亚烷二硫基取代,并且该亚烷二基,亚烷二氧基或亚烷二硫基和与它相连的碳原子一起形成另外的五元至八元螺环,或
A、B和与它们相连的碳原子优选代表C3-C8-螺环,其中的二个取代基-起代表任选被烷基、烷氧基或卤素取代并且可被氧或硫间隔的饱和或不饱和五元或六元环。
A特别优选代表氢、各自任选被卤素取代的C1-C10-烷基、C3-C6-烯基、C1-C8-烷氧基-C2-C6-烷基、C1-C8-多烷氧基-C2-C6-烷基、C1-C8-烷硫基-C2-C6-烷基、任选被1至2个氧和/或硫原子间隔的具有3至7个环原子的环烷基或各自任选被卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和/或硝基取代的苯基、噻吩基、吡啶基、咪唑基、吡唑基、三唑基、吲哚基、噻唑基或苯基-C1-C4-烷基。
B特别优选代表氢、C1-C10-烷基或C1-C6-烷氧基烷基,或者
A、B和与它们相连的碳原子特别优选代表饱和或不饱和的C3-C9-螺环,所述螺环任选被C1-C6-烷基、C3-C8-环烷基、C1-C3-卤代烷基、C1-C6-烷氧基、C1-C6-硫代烷基、氟、氯或苯基单取代或多取代并且任选被氧或硫间隔,或者
A、B和与它们相连的碳原子特别优选代表C3-C6-螺环,所述螺环被任选为一个或二个氧或硫原子所间隔的亚烷二基、或被亚烷二氧基或亚烷二硫基取代,并且该亚烷二基、亚烷二氧基或亚烷二硫基和与它相连的碳原子一起形成另外的五元至七元螺环,或者
A、B和与它们相连的碳原子特别优选代表C3-C6-螺环,其中二个相邻的取代基一起代表被C1-C3-烷基、C1-C3-烷氧基、氟、氯或溴取代并且可被氧或硫间隔的饱和或不饱和五元或六元环。
A最优选代表氢、各自任选被卤素取代的C1-C8-烷基、C3-C4-烯基、C1-C6-烷氧基-C2-C4-烷基、C1-C4-多烷氧基-C2-C4-烷基、C1-C6-烷硫基-C2-C4-烷基、任选被1至2个氧和/或硫原子间隔的具有3至6个环原子的环烷基或各自任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基和/或硝基取代的苯基、噻吩基、吡啶基、咪唑基、吡唑基、三唑基、吲哚基、噻唑基或苯基-C1-C3-烷基。
B最优选代表氢、C1-C8-烷基或C1-C4-烷氧基烷基,或
A、B和与它们相连的碳原子最优选代表饱和或不饱和的C3-C8-螺环,所述螺环任选被甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、环己基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、氟、氯或苯基单取代或多取代并且任选被氧或硫间隔,或
A、B和与它们相连的碳原子最优选代表C3-C6-螺环,所述螺环被任选为一个氧或硫原子所间隔的亚烷二基或被亚烷二氧基取代,并且该亚烷二基或亚烷二氧基和与它相连的碳原子一起形成另外的五至七元螺环,或
A、B和与它们相连的碳原子最优选代表C3-C6-螺环,其中二个取代基一起代表可被氧或硫间隔的饱和或不饱和五元或六元环。
X优选代表卤素或C1-C6-烷氧基。
X特别优选代表卤素或C1-C4-烷氧基。
X最优选代表氟、氯、溴、甲氧基、乙氧基、丙氧基或异丙氧基。
Y优选代表氢、卤素或C1-C6-烷氧基。
Y特别优选代表氢、卤素或C1-C4-烷氧基。
Y最优选代表氢、氟、氯、溴、甲氧基、乙氧基、丙氧基或异丙氧基。
Z优选代表氢、卤素或C1-C6-烷氧基。
Z特别优选代表氢、卤素或C1-C4-烷氧基。
Z最优选代表氢、氟、氯、溴、甲氧基、乙氧基、丙氧基或异丙氧基。
在所有情况下,X和Y或X和Z不同时为卤素。
其中
E代表金属离子等价物或铵离子,和
L和M各自代表氧或硫。
R1优选代表各自任选被卤素取代的C1-C20-烷基、C2-C20-烯基、C1-C8-烷氧基-C1-C8-烷基、C1-C8-烷硫基-C1-C8-烷基、C1-C8-多烷氧基-C2-C8-烷基或具有3至8个环原子的环烷基,它可被氧和/或硫原子间隔,
任选被卤素、硝基、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C1-C6-烷硫基或C1-C6-烷基磺酰基取代的苯基,
任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C6-卤代烷基或C1-C6-卤代烷氧基取代的苯基-C1-C6-烷基,
任选被卤素和/或C1-C6-炕基取代的杂芳基,
任选被卤素和/或C1-C6-烷基取代的苯氧基-C1-C6-烷基,
任选被卤素、氨基和/或C1-C6-烷基取代的杂芳氧基-C1-C6-烷基;
R2优选代表各自任选被卤素取代的C1-C20-烷基、C3-C20-烯基、C1-C8-烷氧基-C2-C8-烷基或C1-C8-多烷氧基-C2-C8-烷基,
任选被卤素、C1-C4-烷基和/或C1-C4-烷氧基取代的C3-C8-环烷基,或者
各自任选被卤素、硝基、C1-C6-烷基、C1-C6-烷氧基和/或C1-C6-卤代烷基取代的苯基或苄基;
R3、R4和R5各自独立地优选代表各自任选被卤素取代的C1-C8-烷基、C1-C8-烷氧基、C1-C8-烷基氨基、二-(C1-C8)-烷基氨基、C1-C8-烷硫基、C3-C6-烯硫基、C3-C7-环烷基硫基或各自任选被卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基、C1-C4-烷基或C1-C4-卤代烷基取代的苯基、苯氧基或苯硫基;
R6和R7各自独立地优选代表氢、各自任选被卤素取代的C1-C8-烷基、C3-C8-环烷基、C1-C8-烷氧基、C3-C8-烯基、C1-C8-烷氧基-C2-C8-烷基、任选被卤素、C1-C8-卤代烷基、C1-C8-烷基和/或C1-C8-烷氧基取代的苯基、任选被卤素、C1-C8-烷基、C1-C8-卤代烷基和/或C1-C8-烷氧基取代的苄基、或者与和它们连接的N原子一起代表任选被氧或硫间隔的C3-C6-亚烷基环。
G特别优选代表氢(a)或下列基团:
其中
E代表金属离子等价物或铵离子,和
L和M各自代表氧或硫;
R1特别优选代表各自任选被卤素取代的C1-C16-炕基、C2-C16-烯基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷硫基-C1-C6-烷基、C1-C6-多烷氧基-C2-C6-烷基或具有3至7个环原子的环烷基,它可被1个或2个氧和/或硫原子间隔,
任选被卤素、硝基、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基、C1-C3-卤代烷氧基、C1-C4-烷硫基和/或C1-C4-烷基磺酰基取代的苯基,
任选被卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C3-卤代烷基或C1-C3-卤代烷氧基取代的苯基-C1-C4-烷基,
各自任选被氟、氯、溴和/或C1-C4-烷基取代的噻吩基、呋喃基、吡啶基、嘧啶基、噻唑基或吡唑基,
任选被氟、氯、溴和/或C1-C4-烷基取代的苯氧基-C1-C5-烷基,或
各自任选被氟、氯、溴、氨基和/或C1-C4-烷基取代的吡啶氧基-C1-C5-炕基、嘧啶氧基-C1-C5-烷基或噻唑氧基-C1-C5-烷基;
R2特别优选代表各自任选被卤素取代的C1-C16-烷基、C3-C16-烯基、C1-C6-烷氧基-C2-C6-烷基或C1-C6-多烷氧基-C2-C6-烷基,
任选被卤素、C1-C3-烷基和/或C1-C3-烷氧基取代C3-C7-环烷基,或
各自任选被卤素、硝基、C1-C4-烷基、C1-C3-烷氧基和/或C1-C3-卤代烷基取代的苯基或苄基。
R3、R4和R5各自独立地特别优选代表各自任选被卤素取代的C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷基氨基、二-(C1-C6)-烷基氧基、C1-C6-烷硫基、C3-C4-烯硫基、C3-C6-环烷基硫基或各自任选被氟、氯、溴、硝基、氰基、C1-C3-烷氧基、C1-C3-卤代炕氧基、C1-C3-烷硫基、C1-C3-卤代烷硫基、C1-C3-烷基或C1-C3-卤代烷基取代的苯基、苯氧基或苯硫基。
R6和R7各自独立地特别优选代表氢、各自任选被卤素取代的C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、C3-C6-烯基、C1-C6-烷氧基-C2-C6-烷基、任选被卤素、C1-C5-卤代烷基、C1-C5-烷基和/或C1-C5-烷氧基取代的苯基、任选被卤素、C1-C5-烷基、C1-C5-卤代烷基和/或C1-C5-烷氧基取代的苄基、或者与和它们连接的N原子一起代表任选被氧或硫间隔的C3-C6-亚烷基环。
其中
E代表金属离子等价物或铵离子,和
L和M各自代表氧或硫。
R1最优选代表各自任选被氟和/或氯取代的C1-C14-烷基、C2-C14-烯基、C1-C4-烷氧基-C1-C6-烷基、C1-C4-烷硫基-C1-C6-烷基、C1-C4-多烷氧基-C2-C4-烷基或具有3至6个环原子的环烷基,它可被1至2个氧和/或硫原子间隔,
任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基、三氟甲氧基、甲硫基、乙硫基、甲磺酰基、乙磺酰基和/或硝基取代的苯基,
任选被氟、氯、溴、甲基、乙基、丙基、异丙基、甲氧基、乙氧基、三氟甲基和/或三氟甲氧基取代的苯基-C1-C3-烷基,
各自任选被氟、氯、溴、甲基和/或乙基取代的噻吩基、呋喃基、吡啶基、嘧啶基、噻唑基或吡唑基,
任选被氟、氯、甲基和/或乙基取代的苯氧基-C1-C4-烷基,或
各自任选被氟、氯、氨基、甲基和/或乙基取代的吡啶氧基-C1-C4-烷基、嘧啶氧基-C1-C4-烷基或噻唑氧基-C1-C4-烷基;
R2最优选代表各自任选被氟和/或氯取代的C1-C14-烷基、C3-C14-烯基、C1-C4-烷氧基-C2-C6-烷基或C1-C4-多烷氧基-C2-C6-烷基,
任选被氟、氯、甲基、乙基、丙基、异丙基和/或甲氧基取代的C3-C6-环烷基,或
各自任选被氟、氯、硝基、甲基、乙基、丙基、异丙基、甲氧基、乙氧基和/或三氟甲基取代的苯基或苄基。
R3、R4和R5各自独立地最优选代表各自任选被氟和/或氯取代的C1-C4-烷基、C1-C4-烷氧基、 C1-C4-烷基氨基、二-(C1-C4)-烷基氨基、C1-C4-烷硫基、或各自任选被氟、氯、溴、硝基、氰基、C1-C2-烷氧基、C1-C2-氟代烷氧基、C1-C2-烷硫基、C1-C2-氟代烷硫基和/或C1-C3-烷基取代的苯基、苯氧基或苯硫基。
R6和R7各自独立地最优选代表氢、各自任选被氟、氯和/或溴取代的C1-C4-烷基、C3-C6-环烷基、C1-C4-烷氧基、C3-C4-烯基、C1-C4-烷氧基-C2-C4-烷基、任选被氟、氯、溴、C1-C4-卤代烷基、C1-C4-烷基和/或C1-C4-烷氧基取代的苯基、任选被氟、氯、溴、C1-C4-烷基、C1-C4-卤代烷基和/或C1-C4-烷氧基取代的苄基、或者与和它们连接的N原子一起代表任选被氧或硫间隔的C3-C6-亚烷基环。
除非另有说明,烷基及象例如在烷氧基中那样的与杂原子结合的烷基可能为直链或支链。
前面所述的基团或图式的一般定义或基团或图式定义的优选范围可根据需要相互结合,这就是说特定范围和优选范围间的结合也是可能。它们适用于终产物,同时也类似地适用于前体物和中间体。
根据本发明,优选的是那些具有前述优选定义的组合的通式(I)化合物。
根据发明特别优选的是那些具有前述特别优选定义组合的通式(I)化合物。
根据发明最优选的是那些具有前述最优选定义组合的通式(I)化合物。
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ia)的化合物:
表1续表1续表1续
表1续表1续表1续表1续
表1续:
X | Y | Z | A | B |
Cl | OCH3 | H | CH3 | H |
Cl | OCH3 | H | C2H5 | H |
Cl | OCH3 | H | C3H7 | H |
Cl | OCH3 | H | i-C3H7 | H |
Cl | OCH3 | H | C4H9 | H |
Cl | OCH3 | H | i-C4H9 | H |
Cl | OCH3 | H | s-C4H9 | H |
Cl | OCH3 | H | t-C4H9 | H |
X | Y | Z | A | B |
OCH3 | Cl | H | CH3 | H |
OCH3 | Cl | H | C2H5 | H |
OCH3 | Cl | H | C3H7 | H |
OCH3 | Cl | H | i-C3H7 | H |
OCH3 | Cl | H | C4H9 | H |
OCH3 | Cl | H | i-C4H9 | H |
OCH3 | Cl | H | s-C4H9 | H |
OCH3 | Cl | H | t-C4H9 | H |
OCH3 | Cl | H | CH3 | CH3 |
OCH3 | Cl | H | C2H5 | CH3 |
OCH3 | Cl | H | C3H7 | CH3 |
OCH3 | Cl | H | i-C3H7 | CH3 |
OCH3 | Cl | H | C4H9 | CH3 |
OCH3 | Cl | H | i-C4H9 | CH3 |
OCH3 | Cl | H | s-C4H9 | CH3 |
OCH3 | Cl | H | t-C4H9 | CH3 |
OCH3 | Cl | H | C2H5 | C2H5 |
OCH3 | Cl | H | C3H7 | C3H7 |
X | Y | Z | A | B |
OCH3 | Cl | H | -(CH2)2- | |
OCH3 | Cl | H | -(CH2)4- | |
OCH3 | Cl | H | -(CH2)5- | |
OCH3 | Cl | H | -(CH2)6- | |
OCH3 | Cl | H | -(CH2)7- | |
OCH3 | Cl | H | -(CH3)2-O-(CH3)2- | |
OCH3 | Cl | H | -(CH2)2-S-(CH2)2- | |
OCH3 | Cl | H | -CH2-CHCH3-(CH2)3- | |
OCH3 | Cl | H | -(CH2)2-CHCH3-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHC2H5-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHC3H7-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHi-C3H7-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHOCH3-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHOC2H5-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHOC3H7-(CH2)2- | |
OCH3 | Cl | H | -(CH2)2-CHi-OC3H7-(CH2)2- |
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ib)的化合物:表2:表2续表2(续)表2续表2续表2续表2续表2续表2续表2续表2续表2续表2续表2续表2续表2续表2续 ed:表2续 ed:表2续:
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ic)的化合物:表3
表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续表3续:
X | Y | Z | A | B | L | M | R2 |
Cl | OCH3 | H | CH3 | H | O | O | C2H5 |
Cl | OCH3 | H | C2H5 | H | O | O | C2H5 |
Cl | OCH3 | H | C3H7 | H | O | O | C2H5 |
Cl | OCH3 | H | i-C3H7 | H | O | O | C2H5 |
Cl | OCH3 | H | C4H9 | H | O | O | C2H5 |
Cl | OCH3 | H | i-C4H9 | H | O | O | C2H5 |
Cl | OCH3 | H | s-C4H9 | H | O | O | C2H5 |
Cl | OCH3 | H | t-C4H9 | H | O | O | C2H5 |
Cl | OCH3 | H | CH3 | CH3 | O | O | C2H5 |
Cl | OCH3 | H | C2H5 | CH3 | O | O | C2H5 |
Cl | OCH3 | H | C3H7 | CH3 | O | O | C2H5 |
Cl | OCH3 | H | i-C3H7 | CH3 | O | O | C2H5 |
Cl | OCH3 | H | C4H9 | CH3 | O | O | C2H5 |
Cl | OCH3 | H | i-C4H9 | CH3 | O | O | C2H5 |
除在制备实例中提到的化合物以外,还可逐一列出下列式(Id)的化合物:表4
表4续表4续表4续表4续表4续表4续
Y | Z | A | B | R3 | |
Cl | OCH3 | H | CH3 | H | CH3 |
Cl | OCH3 | H | C2H5 | H | CH3 |
Cl | OCH3 | H | C3H7 | H | CH3 |
Cl | OCH3 | H | i-C3H7 | H | CH3 |
Cl | OCH3 | H | C4H9 | H | CH3 |
Cl | OCH3 | H | i-C4H9 | H | CH3 |
Cl | OCH3 | H | s-C4H9 | H | CH3 |
Cl | OCH3 | H | t-C4H9 | H | CH3 |
Cl | OCH3 | H | CH3 | CH3 | CH3 |
Cl | OCH3 | H | C2H5 | CH3 | CH3 |
Cl | OCH3 | H | C3H7 | CH3 | CH3 |
Cl | OCH3 | H | i-C3H7 | CH3 | CH3 |
Cl | OCH3 | H | C4H9 | CH3 | CH3 |
Cl | OCH3 | H | i-C4H9 | CH3 | CH3 |
Cl | OCH3 | H | s-C4H9 | CH3 | CH3 |
Cl | OCH3 | H | t-C4H9 | CH3 | CH3 |
Cl | OCH3 | H | C2H5 | C2H5 | CH3 |
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ie)的化合物:表5:
表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续表5续
X | Y | Z | A | B | L | R4 | R5 |
Cl | OCH3 | H | CH3 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | C2H5 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | C3H7 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | i-C3H7 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | C4H9 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | i-C4H9 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | s-C4H9 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | t-C4H9 | H | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | CH3 | CH3 | S | CH3 | i-C3H7-S- |
Cl | OCH3 | H | C2H5 | CH3 | S | CH3 | i-C3H7-S- |
除在制备实例中提到的化合物以外,还可逐一列出下列式(If-a)的化合物:表6a:
表6a续表6a续表6a续表6a续表6a续表6a续
X | Y | Z | A | B |
Cl | OCH3 | H | CH3 | H |
Cl | OCH3 | H | C2H5 | H |
Cl | OCH3 | H | C3H7 | H |
Cl | OCH3 | H | i-C3H7 | H |
Cl | OCH3 | H | C4H9 | H |
Cl | OCH3 | H | i-C4H9 | H |
Cl | OCH3 | H | s-C4H9 | H |
Cl | OCH3 | H | t-C4H9 | H |
Cl | OCH3 | H | CH3 | CH3 |
Cl | OCH3 | H | C2H5 | CH3 |
除在制备实例中提到的化合物以外,还可逐一列出下列式(If-b)的化合物:表6b:
表6b续表6b续表6b续表6b续表6b续表6b续
X | Y | Z | A | B |
Cl | OCH3 | H | CH3 | H |
Cl | OCH3 | H | C3H5 | H |
Cl | OCH3 | H | C3H7 | H |
Cl | OCH3 | H | i-C3H7 | H |
Cl | OCH3 | H | C4H9 | H |
Cl | OCH3 | H | i-C4H9 | H |
Cl | OCH3 | H | s-C4H9 | H |
Cl | OCH3 | H | t-C4H9 | H |
Cl | OCH3 | H | CH3 | CH3 |
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ig-a)的化合物:表7a:
表7a续表7a,续表7a,续表7a,续表7a,续表7a,续
X | Y | Z | A | B |
Cl | OCH3 | H | CH3 | H |
Cl | OCH3 | H | C2H5 | H |
Cl | OCH3 | H | C3H7 | H |
Cl | OCH3 | H | i-C3H7 | H |
Cl | OCH3 | H | C4H9 | H |
Cl | OCH3 | H | i-C4H9 | H |
Cl | OCH3 | H | s-C4H9 | H |
Cl | OCH3 | H | t-C4H9 | H |
除在制备实例中提到的化合物以外,还可逐一列出下列式(Ig-b)的化合物:表7b:
表7b续表7b续表7b续表7b续表7b续表7b续
X | Y | Z | A | B |
Cl | OCH3 | H | CH3 | H |
Cl | OCH3 | H | C2H5 | H |
Cl | OCH3 | H | C3H7 | H |
Cl | OCH3 | H | i-C3H7 | H |
Cl | OCH3 | H | C4H9 | H |
Cl | OCH3 | H | i-C4H9 | H |
Cl | OCH3 | H | s-C4H9 | H |
如果按照方法(Aβ),用N-(2-氯-4-氟苯乙酰基)-2-氨基-2,3-二甲基-丁酸甲酯作起始物,则本发明方法的反应过程可用下式说明:
如果按照方法(Bβ),用3-(2-溴-6-甲氧基苯基)-5-异丙基-5-甲基-吡咯烷-2,4-二酮和乙酸酸酐作起始物,则本发明方法的反应过程可用下式说明:
如果按照方法(c),用3-(2-甲氧基-2-氯苯基)-5,5-二乙基-吡咯烷-2,4-二酮和氯甲酸乙氧乙基酯作起始物,则本发明方法的反应过程可用下式说明:
如果按照方法(Hα),用3-(2-氯-4-乙氧基苯基)-5,5-亚己基-吡咯烷-2,4-二酮和异氰酸乙酯作起始物,则反应过程可用下式说明:
如果按照方法(Hβ),用3-(2-甲氧基-4-氯苯基)-5-甲基-吡咯烷-2,4-二酮和二甲基氨基甲酰氯作起始物,则反应过程可用下式说明:在本发明的方法(A)中被用作起始物的式(II)的化合物是新的,其中
R12代表氢(XIVa)或烷基(XIVb),和
A和B具有前述的定义。与式(XV)的苯基乙酰卤进行酰化反应(Chem.Reviews 52,237-416(1953));Bhattacharya,Indian J. Chem.6,341-5,1968),
其中
X、Y和Z具有前述的定义和
其中
A、B、X、Y和Z具有前述的定义。
式(XIVa)的取代环状氨基羧酸-般通过布赫尔-伯格反应或斯特雷克尔合成法制得并且各种方法制得不同的异构体形式,例如在布赫尔-伯格反应条件下,主要产物是那些原子团R和羧基处于平伏位的异构体(为简单起见后称β异构体〕,而在斯特雷克尔合成条件下主要得到的那些其中氨基和原子团R处于平伏位的异构体(为简单起见后称α异构体)(L. Munday,J.Chem.Soc.4372(1961);J.T Eward C.Jitrangeri,Can,J.Chem.53,3339(1975))。布赫尔-伯格反应(β异构体)斯特雷克尔合成(α异构体)
此外,为制备前面方法(A)所用的式(II)的起始物,
其中
其中
A和B具有前述的定义,与式(XV)的苯基乙酰卤化物反应,
其中
X、Y和Z具有前述的定义,和
Hal代表氯或溴,得到式(XVII)的化合物
其中
A、B、X、Y和Z具有前述的定义,并且随后将这些化合物在硫酸存在下醇解处理。
式(XVII)的化合物也是新的。
除制备实例中提到的中间体以外,还可提及下列式(II)的化合物,这些化合物仅作为实例而非作为限制:
N-(2-氯-4-甲氧基苯乙酰基)-丙氨酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-亮氨酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-异亮氨酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-缬氨酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-氨基异丁酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸甲酯
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-丙氨酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-亮氨酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-异亮氨酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-缬氨酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-氨基异丁酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸甲酯
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-丙氨酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-亮氨酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-异亮氨酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-缬氨酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-氨基异丁酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸甲酯
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-2-甲基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-3-甲基-环己炕羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-4-甲基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-4-乙基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸甲酯
N-(2-氯-4-甲氧基-苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-2-甲基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-3-甲基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-4-甲基-环己炕羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-4-乙基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸甲酯
N-(2-氯-6-甲氧基-苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-2-甲基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-3-甲基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-4-甲基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-4-乙基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸甲酯
N-(4-氯-2-甲氧基-苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸甲酯
除制备实例中提到的中间体以外,可能提到下列仅作为实例而非作为限制的式(IIa)化合物:
N-(2-氯-4-甲氧基苯乙酰基)-丙氨酸
N-(2-氯-4-甲氧基苯乙酰基)-亮氨酸
N-(2-氯-4-甲氧基苯乙酰基)-异亮氨酸
N-(2-氯-4-甲氧基苯乙酰基)-缬氨酸
N-(2-氯-4-甲氧基苯乙酰基)-氨基异丁酸
N-(2-氯-4-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸
N-(2-氯-4-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸
N-(2-氯-4-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-丙氨酸
N-(4-氯-2-甲氧基苯乙酰基)-亮氨酸
N-(4-氯-2-甲氧基苯乙酰基)-异亮氨酸
N-(4-氯-2-甲氧基苯乙酰基)-缬氨酸
N-(4-氯-2-甲氧基苯乙酰基)-氨基异丁酸
N-(4-氯-2-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸
N-(4-氯-2-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸
N-(4-氯-2-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-丙氨酸
N-(2-氯-6-甲氧基苯乙酰基)-亮氨酸
N-(2-氯-6-甲氧基苯乙酰基)-异亮氨酸
N-(2-氯-6-甲氧基苯乙酰基)-缬氨酸
N-(2-氯-6-甲氧基苯乙酰基)-氨基异丁酸
N-(2-氯-6-甲氧基苯乙酰基)-2-乙基-2-氨基丁酸
N-(2-氯-6-甲氧基苯乙酰基)-2-甲基-2-氨基戊酸
N-(2-氯-6-甲氧基苯乙酰基)-2,3-二甲基-2-氨基戊酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环戊烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环庚烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-环辛烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-4-乙基-环己炕羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸
N-(2-氯-4-甲氧基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸
N-( 4-氯-2-甲氧基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸
N-(4-氯-2-甲氧基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-2-甲基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-3-甲基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-4-甲基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-3,4-二甲基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-4-乙基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-4-异丙基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-4-叔丁基-环己烷羧酸
N-(2-氯-6-甲氧基苯乙酰基)-1-氨基-4-甲氧基-环己烷羧酸。
例如由式(XV)的苯乙酰基卤化物和式(XIVa)的氨基酸通过Schotten-Baumann方法可制备式(IIa)的化合物(Organikum,9th.Edition,446(1970)VEB Deutscher Verlag der Wissenschaften,Berrlin)。
其中
X、Y和Z具有前述的定义,和
Hal代表溴或氯。
其中
X、Y和Z具有前述的定义,与象例如碳酰氯、三氯化磷、五氯化磷、三溴化磷、五溴化磷或亚硫酰氯那样的卤化剂反应,反应适宜时在惰性稀释剂如烃或卤代烃的存在下进行,反应温度-30℃至150℃,优选-20℃至100℃。
X、Y和Z在式(XIX)、(XX)、(XXI)和(XVIII)中的定义与前述相同。
式(XIX)的甲苯是有机化学所熟知的化合物。
在实施本发明的方法(B)、(C)、(D)、(E)、(F)、(G)和(H)时,其他作为起始物的式(III)的酰卤、式(IV)的羧酸酐、式(V)的氯甲酸酯或氯甲酸硫酯、式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯、式(XII)的烷基卤化物、式(XIII)的磺酰氯、式(IX)的磷化物或式(X)和(XI)的金属氢氧化物或胺,以及式(XIII)的异氰酸酯、异硫氰酸酯或氨基甲酰氯为有机或无机化学所熟知的化合物。
方法(A)的特征在于将其中A、B、X、Y、Z和R8具有前述定义的式(II)化合物在碱存在下经历分子内缩合反应。
实施本发明方法(A)时可使用的稀释剂为所有惰性有机溶剂。下列溶剂可优选采用:烃类,如甲苯和二甲苯;醚类,如二丁基醚、四氢呋喃、二噁烷、乙二醇二甲基醚和二乙二醇二甲醚;极性溶剂,如二甲亚砜、环丁砜、二甲基甲酰胺和N-甲基-吡咯烷酮;还有醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇和叔丁醇。
实施本发明的方法(A)时可使用的碱(去质子试剂)为所有习用的质子受体。下列碱可优选采用:碱金属和碱土金属的氧化物、氢氧化物和碳酸盐,例如氢氧化钠、氢氧化钾、氧化镁、氧化钙、碳酸钠、碳酸钾和碳酸钙,所有这些碱也可在举例来说如三乙基苄基氯化铵、四丁基溴化铵、Adogen 464(甲基三烷基(C8-C10)氯化铵)或TDA1(=三-(甲氧乙氧基乙基)胺)等相转移催化剂存在下使用。此外可使用如钠或钾等碱金属。另外,碱金属氨化物、碱金属氢化物、碱土金属氨化物和碱土金属氢化物,例如氨化钠、氢化钠和氢化钙,以及碱金属醇化物,如甲醇钠、乙醇钠和叔丁醇钾也可使用。
在实施本发明方法(A)时,反应温度可在相当宽的范围内变化。所述反应一般在0℃~250℃,优选在50℃~150℃温度实施。
方法(A)一般在常压下实施。
在实施本发明的方法(Aα)和(Aβ)时,式(II)和(IIa)的反应物与去质子碱一般按大约2倍等摩尔量使用。但也可能使一种或另一种组分的用量较大过量(最高3mol)。
方法(Bβ)的特征在于使式(Ia)的化合物与式(III)的羧酰卤反应。
如果采用酰卤,则本发明方法(Bβ)中可使用的稀释剂为惰性于这些化合物的所有溶剂。下列溶剂可优选采用:烃类,如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;卤代烃类,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮类,例如丙酮和甲基异丙酮;醚类,如二乙醚、四氢呋喃和二噁烷;羧酸酯类,例如乙酸乙酯;也可使用如二甲基亚砜和环丁砜等强极性溶剂。如果在水解时酰卤相当稳定,则反应也可在水存在下实施。
如果采用对应羧酰卤,则按照本发明方法(Bα)的反应中适合的酸结合剂为所有习用的酸受体。可优选采用下列酸结合剂:叔胺类,如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一烯(DBU)、二氮杂二环壬烯(DBN)、Hunig碱和N,N-二甲基苯胺;碱土金属氧化物,如氧化镁和氧化钙;碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙;氢氧化物,如氢氧化钠和氢氧化钾。
如果采用羧酰卤,则实施本发明方法(Bα)时的反应温度可在相当宽的范围内变化。一般说来,所述方法在-20℃~+150℃,优选0℃~100℃温度下实施。
在实施本发明的方法(Bα)时,式(Ia)的起始物与式(III)的羧酰卤一般为按大约等摩尔量使用。但也可能使羧酰卤的用量较大过量(高至5mol)。后处理按习用方法进行。
方法(Bβ)的特征在于使式(Ia)的化合物与式(IV)的羧酸酐反应。
在本发明的方法(Bβ)中,如果将羧酸酐作为式(IV)的反应物使用,则反应所用稀释剂优选那些使用酰基卤时也优选的溶剂。此外,过量的羧酸酐也可同时作为稀释剂。
使用羧酸酐时,实施本发明方法(Bβ)的反应温度可在相当宽的范围内变化。一般情况下,所述方法在-20℃~+150℃,优选0℃~100℃温度下实施。
在实施本发明的方法(Bβ)时,式(Ia)的起始物和式(IV)的羧酸酐一般按大约等摩尔量使用。但也可能使羧酸酐的用量较大过量(高至5mol)。后处理按习用方法进行。
一般来说,随后经蒸馏或用有机溶剂或水洗涤的方法除去稀释剂和过量的羧酸酐,及其生成的羧酸。
方法(C)的特征在于使式(Ia)的化合物与式(V)的氯甲酸酯或氯甲酸硫酯反应。
如果采用相应的氯甲酸酯或氯甲酸硫酯,则本发明方法(C)的反应中适合的酸结合剂为所有习用的酸受体。可优选采用下列酸结合剂:叔胺类,如三乙胺、吡啶、DABCO、DBU、DBA、Hunig碱和N,N-二甲基苯胺;碱土金属氧化物,如氧化镁和氧化钙;碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠、碳酸钾和碳酸钙;还可使用碱金属氢氧化物,如氢氧化钠和氢氧化钾。
采用氯甲酸酯或氯甲酸硫酯时,本发明方法(C)中可使用的稀释剂为惰性于这些化合物的所有溶剂。下列溶剂可优选采用:烃类,如汽油、苯、甲苯、二甲苯和1,2,3,4-四氢化萘;卤代烃类,例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯;酮类,例如丙酮和甲基异丙酮;醚类,如二乙醚、四氢呋喃和二噁烷;羧酸酯类,例如乙酸乙酯;也可使用如二甲基亚砜和环丁砜等强极性溶剂。
如果采用氯甲酸酯或氯甲酸硫酯作为式(V)的羧酸衍生物,则实施本发明方法(C)时的反应温度可在相当宽的范围内变化。在稀释剂和酸结合剂存在下实施本方法的反应温度通常为-20℃~+100℃,优选0℃~50℃。
本发明的方法(C)一般在常压下实施。
在实施本发明的方法(C)时,式(Ia)的起始物与相应的式(V)的氯甲酸酯或氯甲酸硫酯一般按大约等当量使用。但也可能使一种或另一种组分的用量较大过量(至2mol)。然后按习用方法进行后处理。随后的处理一般是除去沉淀的盐并用稀释剂反萃取方法浓缩剩余的反应混合物。
在制备方法(Dα)中,将大约1mol式(VI)的氯单硫代甲酸酯或氯二硫代甲酸酯在0~120℃,优选20~60℃温度下与每摩尔式(Ia)的起始物反应。
适合任选地加入的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、砜类、亚砜类以及卤代烷类。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果在优选实施方案中通过加入举例来说如氢化钠或叔丁醇钾等强去质子试剂合成化合物(Ia)的烯醇盐,则可省去另外加入酸结合剂。
如果使用酸结合剂,那么习用的无机或有机碱类是适合的,并且举例来说可能提到氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在常压或增压下进行,优选在常压下进行。以习用方法进行后处理。
在制备方法(Dβ)中,每摩尔式(Ia)的起始化合物加入等摩尔量或过量的二硫化碳。此方法优选在0~50℃,特别是20~30℃的温度下实施。
通过加入去质子试剂(举例来说如叔丁醇钾或氢化钠)首先制备出式(Ia)化合物的对应盐常常是有利的。式(Ia)的化合物与二硫化碳反应,比如在室温下搅拌几小时后至完全生成中间产物。
产物进一步与式(VII)的烷基卤化物反应,反应温度优选0~70℃,特别优选20~50℃。反应时至少使用等摩尔量的烷基卤化物。
本方法一般在常压或增压下实施,优选在常压下实施。
本方法仍然以习用方法进行后处理。
实施制备方法(E)时,使大约1mol的磺酰氯(VIII)与每摩尔式(Ia)的起始化合物在-20~150℃,优选在20~70℃温度下反应。
适合任选加入的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、腈类、砜类、亚砜类或二氯甲烷等卤化烃类。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺、二甲硫醚或二氯甲烷。
如果在优选实施方案中通过加入举例来说如氢化钠或叔丁醇钾等强去质子试剂合成化合物(Ia)的烯醇盐,则可省去另外加入酸结合剂。
如果使用酸结合剂,那么习用的无机或有机碱类是适合的,并且举例来说可能提到氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在常压或增压下进行,优选在常压下进行。以习用方法进行后处理。
在制备方法(F)中为得到结构(Ie)的化合物,使1~2,优选1~1.3mol的式(IX)的磷化合物与每摩尔式(Ia)的化合物反应,反应温度-40℃~150℃,优选-10~110℃。
适合任选加入的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、腈类、醇类、硫化物类、砜类和亚砜类等。
优选使用乙腈、二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
适合任选加入的酸结合剂是习用的无机或有机碱类,例如氢氧化物、碳酸盐或胺。举例来说可能提到氢氧化钠、碳酸钠、碳酸钾、吡啶和三乙胺。
反应可在常压或增压下进行,优选在常压下进行。后处理用有机化学的习用方法进行。所得终产物用结晶、色谱或所谓的“初期蒸馏(Andestillieren)”,即在真空中除去挥发组分的方法更好地精制。
方法(G)的特征在于使式(Ia)的化合物与金属化合物(X)或胺(XI)反应。
本发明方法中使用的稀释剂可优选醚类,例如四氢呋喃、二噁烷或二乙醚;醇类,如甲醇、乙醇或异丙醇;以及水。
本发明方法(G)一般在常压下实施。反应温度一般在-20~100℃,优选0℃~50℃。
实施制备方法(Hα)时,使大约1mol式(XII)的异氰酸酯与每摩尔式(Ia)的起始化合物在0~100℃,优选20~50℃温度下反应。
适合任选加入的稀释剂是所有惰性有机溶剂,例如醚类、酰胺类、腈类、砜类或亚砜类。
适宜时可加入催化剂促进反应进行。使用时非常便利的催化剂举例来说如二月桂酸二丁基锡等有机锡化合物。本方法优选在常压下实施。
实施制备方法(Hβ)时,使大约1mol的式(VIII)的甲氨酰氯与每摩尔式(Ia)的起始化合物在0~150℃,优选20~70℃温度下反应。
适合任选加入的稀释剂为所有惰性极性有机溶剂,例如醚类、酰胺类、砜类、亚砜类以及卤代烷类。
优选使用二甲亚砜、四氢呋喃、二甲基甲酰胺或二氯甲烷。
如果在优选实施方案中通过加入举例来说如氢化钠或叔丁醇钾等强去质子试剂合成化合物(Ia)的烯醇盐,则可省去另外加入的酸结合剂。
如果使用酸结合剂,那么习用的无机或有机碱类是适合的,并且举例来说可能提到氢氧化钠、碳酸钠、碳酸钾、三乙胺和吡啶。
反应可在常压或增压下进行,优选在常压下进行。以习用方法进行后处理。
活性化合物适用于防治动物害虫,优选节肢动物和线虫,特别是农业、林业以及储存产品和材料的保护以及卫生部门中出现的昆虫和蜘蛛纲动物。它们对于通常敏感和有抗性的物种及其全部或部分发育阶段均具有活性。上述害虫包括:
等足目,例如潮虫、平甲虫和鼠妇。
倍足目,例如具斑马陆。
唇足目,例如食果地蜈蚣和蛐蜒属。
扁肩象目,例如庭院么蛐。
缨尾目,例如西洋衣鱼。
弹尾目,例如具刺跳虫。
直翅目,例如东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国蠊、家蟋蟀、蝼蛄属、热带飞蝗、殊种蚱蜢和沙漠蝗。
革翅目,例如欧洲球螋。
等翅目,例如犀白蚁属。
虱目,例如葡萄瘤蚜、绵蚜属、体虱、血虱属和长颚虱属。
食毛目,例如嚼虱属和畜虱属。
缨翅目,例如温室条蓟马和葱蓟马。
异翅亚目,例如扁盾蝽属、红蝽属、方背皮蝽属、温带臭虫、长红蜡蝽和蜡蝽属。
半翅目,例如甘蓝粉虱、木薯粉虱、温室粉虱、棉蚜、甘蓝蚜、茶蔗隐瘤蚜、Doralis fabae,Doralia Pomi,苹果绵蚜、桃大尾蚜、稠李溢管蚜、微叶蝉属、双叶叶蝉、黑尾时蝉、麦长管蚜、瘤蚜属、忽布庞蚜、李蜡蚧、油榄黑盔蚧、灰飞虱、稻褐飞虱、红圆蚧、夹竹桃圆蚧、粉蚧属和木虱属。
鳞刺目,例如棉红蛉虫、松天蚜、冬天蛾、苹细蛾、苹果巢蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾、桔叶潜蛾、地虎属、刀根虫属、夜蛾属、棉斑实蛾、实夜蛾属、甜菜夜蛾、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、粘虫属、粉纹夜蛾、苹蠢蛾、粉蝶属、螟属、玉米螟、地中海粉螟、大蜡螟、负袋衣蛾、织网衣蛾、褐织衣蛾、亚麻黄卷蛾、具网卷叶蛾、云松卷蛾、葡萄果蠢蛾、茶长卷蛾和栎绿卷叶蛾。
鞘翅目,例如具斑窃蠢、谷蠢、豆象、大豆象、家天牛、赤杨紫跳甲、马铃薯甲虫、辣根猿叶虫、叶甲属、油菜蓝跳甲、墨西哥豆飘虫、隐金甲属、锯谷盗、花象甲属、谷象属、葡萄黑象甲、香焦根象甲、甘蓝荚象甲、苜蓿叶象甲、皮蠢属、斑皮蠢属、圆皮蠢属、毛皮蠢属、粉蠢属、油菜花露尾甲、蛛甲属、金黄蛛甲、麦蛛甲、拟谷盗属、大黄粉虫、叩甲属、金针虫属。西方五月鳃角金龟、六月金龟和褐新西兰翅鳃角金龟。
膜刺目,例如锯角叶蜂属、叶蜂属。蚁尾属、厕蚁和胡蜂属。
双翅目,如伊蚊属、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、厩螯蝇属、狂蝇属、皮蝇属、虻属、螗蜩属、花圆毛蚊、瑞典麦杆蝇、麦花蝇属、菠菜潜叶花蝇、地中海实蝇、油榄实蝇和欧洲大蚊。
蚤目,如印度客蚤和毛列蚤属。
蛛形纲,如蝎和盗蛛。
蜱螨目,如粗脚粉螨、锐喙蜱螨、钝喙蜱螨、鸡皮刺螨、茶蔗瘿螨、桔芸锈螨、牛蜱螨、扁头蜱属、花蜱属、璃眼蜱属、硬蜱属、痒螨属、皮痒螨属、疥螨属、附线螨属、苜蓿螨、全爪螨属和叶螨属。
本发明的活性化合物表现出强有力的杀虫和杀螨的活性。
它们可特别成功地应用于植物害虫的防治,举例说来如防治辣根猿叶甲(Phaedon cochleariae)的幼虫、黑尾叶蝉(Nephottetix cineticeps)的幼虫或防治菜蛾毛虫(Plutella maculipennis)。
本发明的化合物还表现出良好的杀灭苹果黑星菌(Venturia inaequalis)活性。
活性化合物可调制成常规的制剂,如溶液剂、乳液剂、可湿性粉剂、悬浮液剂、粉末剂、尘剂、糊剂、可溶性粉剂、颗粒剂、悬浮液/乳液浓缩液剂、浸泡了活性化合物的天然和合成材料,以及在高分子物质中的微胶囊剂。
这些制剂用已知方法制成,例如通过下述方法:任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物和稀释剂(即液体溶剂和/或固体载体)混合。
如果采用水作稀释剂,则也可用(例如)有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘)、氯化芳族化合物或氯代脂族烃类(如氯苯、氯乙烷或二氯甲烷)、脂族烃类(如环己烷或烷属烃、如矿物油馏分、矿物油和植物油)、醇类(如丁醇或乙二醇及它们的醚或酯)、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);适用的固体载体有:如铵盐和研碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱土和硅藻土)和研碎的合成矿物(如高分散度硅石、氧化铝和硅酸盐);适用的固体颗粒载体有: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)及合成的无机颗粒和有机粉,和有机材料颗粒(如锯末、椰壳、玉米棒碎块和烟叶杆);适用的乳化剂和/或起泡剂有:如非离子型和阴离子型乳化剂(如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如烷芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基硫酸盐及蛋清水解产物);适用的分散剂有:如亚硫酸纸浆废液和甲基纤维素。
在制剂中可使用粘合剂,例如羧甲基纤维素和粉状、颗粒状或胶乳状天然和合成高聚物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯以及天然磷脂,如脑磷脂和卵磷脂以及合成磷脂。其它添加剂可为矿物油和植物油。
可使用着色剂,如无机颜料(例如氧化铁、氧化钛和普鲁士蓝)和有机染料(如茜素染料、偶氮染料和金属酞菁染料)以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有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可存在于其市售制剂中和存在于由这些制剂制得的使用形式中,如和其它活性剂(如杀虫剂、引诱剂、消毒剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂)的混合物。这些杀虫剂包括,例如磷酸酯,氨基甲酸酯、羧酸酯、氯代烃类,苯脲和微生物等产出的物质。
可列举下列化合物:
acrinathrin、alphamethrin、betacyfluthrin、bifenthrin、brofenprox、Cis-resmethrin、clocythrin、cycloprothrin、cyfluthrin、cyhalothrin、腈二氯苯醚菊脂、deltamethrin、esfenvalerate、etofenprox、分扑菊酯、杀灭菊酯、flucythrinate、fluvalmate lambda-cyhalothrin、二氯苯醚菊脂、pyresmethrin、除虫菊、Silafluofen、tralomethrin、zetamethrin;
alanycarb、苯恶威、benfuracarb、混戊威、丁叉威、西维因、巴丹、乙硫甲威、fenobucarb、fenoxycarb、异丙威、甲硫威、乙肟威、metolcarb、草肟威、灭定威、甲丙威、残杀威、叔丁威、 thiodiearb、特氨叉威、trimethacarb、二甲威、xylylcarb;
乙酰甲胺磷、谷硫磷-A、谷硫磷-M、溴硫磷~A、Cadusafos、三硫磷、毒虫畏、氯甲硫磷、毒死蜱、Chlorpyrifos M、杀螟腈、甲基内吸磷、异吸磷-II、异-0五九-II、地亚农、敌敌畏、dicliphos、氯线磷、百治磷、乐果、dimethylvinphos、二噁硫磷、乙拌磷、克瘟散、乙硫磷、乙嘧硫磷、杀螟松、倍硫磷、地虫硫磷、安果、庚虫磷、iprobenfos、异丙三唑硫磷、异噁唑硫磷、马拉硫磷、灭蚜硫磷、mervinphos、mesulfenphos、丁烯硫磷、甲胺磷、三溴磷、氧化乐果、砜吸硫磷、oxydeprofos、对硫磷-A、对硫磷-M、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、肟硫磷、嘧啶硫磷-A、嘧啶硫磷-M、丙虫磷、低毒硫磷、发果、Pyraclophos、打杀磷、喹硫磷、杀虫松、Sebufos、硫特谱、乙丙硫磷、杀虫畏、双硫磷、二甲硫吸磷、嗪线磷、敌百虫、三唑硫磷、完灭硫磷;
buprofezin、chlorfluazuron、伏虫脲、flucycloxuron、flufenoxuron、hexaflumuron、pyriproxfen、tebufenozide、teflubenzuron、triflumuron;
imidacloprid、nitenpyram;
abamectin、amitrazin、avermectin、azadirachtin、bensultap、杀虫素、Cyromazine、diafenthiuron、emamectin、ethofenprox、fenpyrad、fipronil、flufenprox、lufenuron、蜗牛敌、milbemectin、Pymetrozine、tebufenpyrad、triazuron;
涕灭威、苯噁威、benfuracarb、呋喃丹、carbosulfan、chlorethoxyfos、cloethocarb、乙拌磷、丙线磷、乙嘧硫磷、克线磷、fipronil、地虫硫磷、fosthiazate、furathiocarb、六六六、异丙三唑硫磷、异丙胺磷、甲硫威、久效磷、Nitenpyram、草肟威、甲拌硫、肟硫磷、低毒硫磷、pyrachlofos、sebufos、silafluofen、tebupirimphos、tefluthrin、特丁磷、thiodicarb、特氨叉威;
唑环锡、butylpyridaben、clofentezine、三环锡、difenthiuron、乙硫磷、emamectin、fenazaquin、螨完锡、fenothiocarb、分扑菊酯、fenpyrad、fenpyroximate、fluazinam、fluazuron、flucycloxuron、flucycloxuron、fluvalinate、fubfenprox、hexythiazox、ivemectin、甲噻硫磷、久效磷、moxidectin、三溴磷、伏杀硫磷、溴丙磷、pyraclofos、pyridaben、pyrimidifen、tebufenpyrad、thuringiensin、triarathene,式的化合物和式的化合物。
本发明的活性化合物还可存在于市售制剂和由这些制剂制得的使用形式中,如和增效剂的混合物。增效剂为强化活性化合物作用的化合物,而加入的增效剂本身不一定是活性的。
由市售剂制得的使用形式中的活性化合物的含量可在一个很宽的限度内变化。活性化合物在使用形式中的农度可为0.0000001至95%(重量)活性化合物,优选0.0001至1%(重量)。
本化合物以适合于使用形式的习用方法进行使用。
活性化合物用于防治卫生领域害虫和储存产品害虫时对木头和泥土具有显著的残效作用(residual action),并且在石灰表面显示良好的碱稳定性。
将溶于150ml无水甲苯的23 8g(0.073mol)N-(2-氯-6-甲氧基苯乙酰基)-2-氨基-2,3-二甲基-丁酸甲酯滴加到沸腾条件下的18.06g(0.16mol)叔丁醇钾于50ml无水四氢呋喃的悬浮液中,并将混合物加热回流1.5小时。反应混合物冷至室温,加入230ml水,分出含水相,甲苯相用110ml水反萃取,合并的含水相在15~20℃下用大约25ml的浓盐酸酸化。将产物吸滤并干燥,得到20.2g(理论值的93%)3-(2-氯-6-甲氧基苯基)-5-异丙基-5-甲基-吡咯烷-2,4-二酮,熔点172-174℃。实施例(Ia-2)
将溶于450ml无水甲苯的71.4g(0.226mol)N-(2-氯-4-氟苯乙酰基)-2-氨基-2,3-二甲基-丁酸甲酯滴加到沸腾条件下的56g(0.498mol)叔丁醇钾于150ml无水四氢呋喃的悬浮液中,并在回流温度下连续搅拌90分钟。反应混合物冷至室温后,加入700ml水,分出有机相并用340ml水再次洗涤。合并的含水相在15-20℃下用大约80ml浓盐酸酸化,吸滤出产物。干燥后得到57.1g(理论值的85%)3-(2-氯-4-甲氧基苯基)-5-异丙基-5-甲基-吡啶烷-2,4-二酮,熔点130-140℃。1H NMR(300 MHz,d6-DMSO):0.78,0.94(2d,6H,5
-CH-(CH3)2));1.3(s,3H,5-CH3;
1.93(m,1H,5-CH(CH3)2);
3.77(s,3H,OCH3);6.8,6.9
(dd,1H,Ar 5-H);7.03(d,
1H,Ar 3-H);7.11(d,1H,
Ar 6-H);7.46(br,1H,NH);
10.77(s,1H,OH).
向70ml无水二氯甲烷中导入4.43g(0.015mol)3-(2-氯-6-甲氧基苯基)-5-异丙基-5-甲基-吡咯烷-2,4-二酮,加入2.1ml三乙胺。在0-10℃下加入于5ml无水二氯甲烷中的1.13ml乙酰氯。并将反应混合物在室温下连续搅拌。薄层色谱检测反应的终点。然后用每次100ml 0.5N氢氧化钠溶液将混合物洗涤二次,有机相经硫酸镁干燥,并真空除去溶剂。
得到4.62g(理论值的91%)3-(2-氯-6-甲氧基苯基)-5-异丙基-5-甲基-4-乙酰氧基-Δ3-吡咯烷-2-酮,熔点70~72℃。
向70ml无水二氯甲烷中导入4.43g(0.015mol)3-(2-氯-6-甲氧基苯基)-5-异丙基-5-甲基-吡咯烷-2,4-二酮并加入2.1ml三乙胺。在0-10℃下加入于5ml无水二氯甲烷中的1.5ml氯甲酸乙酯,并将反应混合物在室温连续搅拌。薄层色谱检测反应终点。然后用每次100ml的0.5N氢氧化钠溶液将混合物洗涤二次,有机相经硫酸镁干燥,并真空除去溶剂。
得到2.68g(理论值的48%)O-[3-(2-氯-6-甲氧基苯基)]-5-异丙基-5-甲基-Δ3-吡咯啉-2-酮-4-基碳酸O-乙酯,熔点104-106℃。
在搅拌和水冷却下将溶于200ml二氯甲烷的29.9g(0.101mol)2-(2-氯-6-甲氧基苯基)-N-(1-氰基-2-(3-甲基)-丁基]-乙酰胺滴加到47g(0.481mol)浓硫酸中,反应混合物的温度升至30℃~40℃,加入结束后将反应混合物在30℃~40℃下进一步搅拌2小时至反应混合物的二氯甲炕相变成无色。随后在冰冷却的同时滴加66ml无水甲醇,反应混合物温度在此步骤中又一次升到40℃。将混合物在40℃-70℃下继续搅拌6小时。后处理时,反应混合物搅拌的同时倒入到460g冰中,并用二氯甲炕萃取,合并的有机相用碳酸氢钠水溶液洗至无酸并经硫酸镁干燥和真空除去溶剂。
得到23.8g(72%理论得率)2-(2-氯-6-甲氧基苯基)-N-[1-甲氧羧基-2-(3-甲基)-丁基]-乙酰胺,熔点76-78℃。实施例(II-2)
将32.7ml三乙胺加到溶于220ml无水四氢呋喃的24.28g(0.117mol)1-氨基-4-甲基-环己烷羧酸甲酯盐酸盐中,并在0~10℃下滴加溶于25ml无水四氢呋喃的25.6(0.117mol)2-氯-6-甲氧基-苯基乙酰氯。反应终止后吸滤出沉淀物,滤液浓缩,剩余物溶于二氯甲烷,混合物用稀盐酸洗涤并干燥,真空蒸发溶剂。经MTB醚/正己烷重结晶后得到30.3g(理论值的73%)顺-N-(2-氯-6-甲氧基-苯乙酰基)-4-甲基-1-氨基环己烷羧酸甲酯,熔点159℃。
在0~10℃并搅拌条件下将溶于50ml无水四氢呋喃的32.9g(0.15mol)2-氯-6-甲氧基苯乙酰基氯滴加到溶于250ml无水四氢呋喃的16.8g(0.15mol)2-氨基-2-甲基-异戊腈和22.4ml(0.16mol)三乙胺中,加入结束后将混合物在室温下搅拌至薄层色谱不再检测出起始产物。后处理时,反应混合物被加到600ml冰水和200ml 1N盐酸的搅拌的混合物中,此混合物用二氯甲烷萃取3次,有机相用碳酸氢钠溶液洗涤,有机相经硫酸镁干燥并真空除去溶剂。
得到29.9g(理论值的67%)2-(2-氯-6-甲氧基苯基)-N-(2-氰基-2-(3-甲基)-丁基]-乙酰胺,熔点104~106℃。实施例(XVII-2)
用类似方法得到2-(4-氯-2-甲氧基苯基)-N-[2-氰基-2-(3-甲基)-丁基]-乙酰胺,熔点110-111℃。实施例(XVII-3)
用类似方法得到2-(2-氯-4-氟苯基)-N-[2-氰基-2-(3-甲基)-丁基]-乙酰胺,熔点109-111℃。实施例(XX-1)
2-氯-6-甲氧基苄基溴
将442g2-氯-6-甲氧基甲苯与516g N-溴琥珀酰亚胺一同溶于2420ml四氯化碳,加入5.8g AIBN并加热回流2小时。将固体滤出并用少量四氯化碳洗涤,浓缩滤液,将留下的剩余物分馏。得到483g无色油。(b.p.100℃/1.4 mbar,m.p.44-47℃).1H NMR(CDCl3):7.24(t,1H);7.03(dd,1H);
6.83(dd,1H);4.76(s,2H);
3.93(s,3H).实施例(XX-2)
4-氯-2-甲氧基苄基溴
将303g4-氯-2-甲氧基甲苯和355g N-溴琥珀酰亚胺一同溶于1665ml四氯化碳,加入4.0g AIBN并加热回流2小时。固体被滤出并用少量四氯化碳洗涤,农缩滤液并将留下的剩余物分馏。得到307g无色油。(b.p.103℃/1.5mbar,m.p.42-45℃).1H NMR(CDCl3):7.29(d,1H);6.95(dd,1H);
6.93(dd,1H);4.95(s,2H);
3.93(s,3H).实施例(XX-3)
2-氯-4-甲氧基苄基溴
将186g 2-氯-4-甲氧基甲苯与212g N-溴琥珀酰亚胺一同溶于1000ml四氯化碳,加入2.4g AIBN并加热回流2小时。固体被滤出并用少量四氯化碳洗涤,浓缩滤液并将留下的剩余物分馏。得到252g橙色油(纯度82%)。1H NMR(CDCl3):7.40(d,1H);7.23(dd,1H);
6.85(dd,1H);4.43(s,2H);
3.88(g,3H).制备式(XXI)的化合物的一般方案
将1.3mol氰化钠导入65ml水中,并加入1.7g相转移催化剂Aliquat336。将混合物加热至70℃并在30分钟时间里滴加溶于200ml甲苯的1mol式(XX)的苄基溴衍生物,混合物加热至70℃保持3~6小时。反应混合物温度冷下来后将其倒入600ml甲苯/600ml水中,分出有机相并用水重复洗涤。有机相经干燥浓缩后将剩余物蒸馏。实施例(XXI-1)
(2-氯-6-甲氧基苯基)乙腈
将溶于410ml甲苯的483g 2-氯-6-甲氧基苄基溴与溶于132ml水的131g氰化钠和3.28g Aliquat 336反应。得到325g无色油(沸点103℃/0.08mbar)。1H NMR(CDl3):7.25(t,1H);7.03(dd,1H);
6.82(dd,1H);3.89(s,3H);
3.83(g,2H).实施例(XXI-2)
(4-氯-2-甲氧基苯基)乙腈
将溶于214ml甲苯的269g 4-氯-2-甲氧基苄基溴与溶于69ml水的68.2g氰化钠和1.8g Aliquat 336反应。得到141g无色油(沸点107℃/0.08mbar)。1H NMR(CDCl3):7.30(d,1H);6.98(dd,1H);
6.90(d,1H);3.89(s,3H);
3.66(s,2H).实施例(XXI-3)
(2-氯-4-甲氧基苯基)乙腈
将溶于900ml二氯甲苯的212g(纯度82%)2-氯-4-甲氧基苄基溴与溶于675ml水的176g氰化钾和15.5g四丁基硫酸氢铵在40℃下反应4小时。后处理后得到157g褐色油(纯度79%)。1H NMR(CDCl3):7.33(d,1H);7.19(dd,1H);
6.91(d,1H);3.87(s,3H);
3.67(s,2H).制备式(XVIII)的化合物的一般方案
将2mol氢氧化钾溶于400ml乙二醇并加入1mol式(XXI)的芳基乙腈。混合物在100℃加热5小时后冷至室温并用800ml水稀释,溶液用20%硫酸酸化至大约pHl。吸滤除去酸,产物用水洗涤并干燥。实施例(XVIII-1)
(2-氯-6-甲氧基苯基)乙酸
将325g 2-氯-6-甲氧基苯基乙腈与溶于690ml乙二醇的171g氢氧化钾反应。得到331g固体(熔点164-165℃)。1H NMR(CDCl3):7.19(t,1H);7.00(dd,1H);
6.80(dd,1H);3.90(s,2H);
3.83(s,3H).实施例(XVIII-2)
(4-氯-2-甲氧基苯基)乙酸
将141g 4-氯-2-甲氧基苯基乙腈和溶于280ml乙二醇的83.2g氢氧化钾反应。得到148g固体(熔点100℃)。1H NMR(CDCl3):8.40-8.90(m br,1H);7.10
(d,1H);6.86(dd,1H);6.89
(d,1H);3.80(s,3H);3.60
(s,2H).实施例(XVIII-3)
(2-氯-4-甲氧基苯基)乙酸
将657g(纯度75%)2-氯-4-甲氧基苯基乙腈与溶于1308ml乙二醇的303g氢氧化钾反应。得到430g固体(熔点83-86℃)。1H NMR(CDCl3):8.10-8.60(m br,1H);7.32
(d,1H);7.16(dd,1H);6.89
(d,1H);3.87(s,3H);3.53
(s,2H).实施例(XV-1)
(2-氯-4-甲氧基苯基)乙酰氯
将160g 2-氯-4-甲氧基苯基乙酸悬浮于210ml甲苯,悬浮液在80℃下与96ml亚硫酰氯一同搅拌至气体挥发停止。除去挥发组份并蒸馏剩余物。得到90g橙色油(薄膜蒸发器中170℃,0.08mbar)。1H NMR(CDCl3):7.29(d,1H);7.14(dd,1H);
6.91(d,1H);4.05(s,2H);
3.90(s,3H).实施例(XV-2)
类似于实施例(XV-1),得到(2-氯-6-甲氧基苯基)乙酰氯,沸点106℃/1.1mbar。实施例(XV-3)
类似于实施例(XV-1),得到(4-氯-2-甲氧基苯基)乙酰氯,沸点111℃/1.1mbar。
实施例A
菜蛾试验
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用水稀释至所需浓度。
将甘蓝(Brassica olearacea)浸入所需浓度的活性化合物制剂中进行处理,在叶子仍为湿的状态时用菜蛾毛虫(Plutella maculipennis)进行侵扰。
经过所需时间后,确定百分死亡率。100%意味着所有菜蛾毛虫都被杀死,0%意味着没有菜蛾毛虫被杀死。
在本实验中,例如活性化合物浓度为0.001%的制备实施例Ia-1、Ia-2和Ib-2的化合物7天后带来至少90%的死亡率,而现有技术中已知的化合物(A)和(B)所产生的死亡率仅10%。
实施例B
棉红螨试验(OP抗性)
溶剂:7份(重量)二甲基甲酰胺
乳化剂:1份(重量)烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时,将1份(重量)的活性化合物与所述量的溶剂和所述量的乳化剂混合,浓液用含乳化剂的水稀释至所需浓度。
将被各种发育期的棉红螨(Tetranychus urticae)严重侵扰的豆类植物(Phaseolus vulgaris)浸入所需浓度的活性化合物制剂中进行处理。
经过所需时间后,确定百分作用率。100%意味着所有棉红螨都被杀死,0%意味着没有棉红螨被杀死。
在本实验中,例如活性化合物浓度为0.00016%的制备实施例Ib-3和Ic-2的化合物7天后带来至少80%的死亡率,而现有技术已知的化合物(D)和(E)却没有产生死亡。
Claims (12)
2.按照权利要求1的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中
A代表氢或C1-C3-烷基;
B代表氢或CH3;或者
A、B和与它们相连的碳原子代表饱和的C3-C9-螺环,所述螺环任选为C1-6单取代或多取代。
3.按照权利要求2的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中A代表CH3或i-C3H7。
4.按照权利要求1的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中A、B和与它们相连的碳原子代表饱和的C6螺环,所述螺环任选为C1-6单取代或多取代。
5.按照权利要求4的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中A、B和与它们相连的碳原子代表饱和的C6螺环,所述螺环任选为CH3单取代。
6.按照权利要求1的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中
X代表卤素或C1-C4-烷氧基,
Y代表氢、卤素或C1-C4-烷氧基,
Z代表氢、卤素或C1-C4-烷氧基;
但X和Y,或X和Z不同时为卤素。
7.按照权利要求6的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物,其中
X代表氯或甲氧基;
Y代表氢、氯或甲氧基;
Z代表氢、氯或甲氧基;
但X和Y,或X和Z不同时为氯。
9.制备权利要求1的式(I〕的1-H-3-芳基-吡咯烷-2,4-二酮衍生物的方法,其特征在于,(A)为制备式(Ia)的1-H-3-芳基-吡咯烷-2,4-二酮或它们的烯醇,其中
其中
A、B、X、Y和Z具有前面提到的定义,和
R8代表烷基;或β)为制备式(Ia-a)的1-H-3-芳基-吡咯烷-2,4-二酮或它们的烯醇,
其中
A、B、X和Z具有前面提到的定义,和
Y1代表-OR8,其中
R8代表烷基;
其中
A、B、X和Z具有前面提到的定义,
Y2代表氟,和
R8代表烷基;或(B)为制备式(Ib)的化合物,
其中
其中
A、B、X、Y和Z具有前面提到的定义,α)适宜时,在稀释剂存在下,并且适宜时在酸结合剂存在下,与通式(III)的酰基卤反应,
其中
R1具有前面提到的定义,和
Hal代表卤素;或β)适宜时,在稀释剂存在下,并且适宜时在酸结合剂存在下,与通式(IV)的羧酸酐反应,
R1-CO-O-CO-R1 (IV)
其中
其中
A、B、X、Y、Z和R2具有权利要求1中所给的定义,并且
其中
A、B、X、Y和Z具有前面提到的定义,适宜时在稀释剂存在下,并且适宜时在酸结合剂存在下,与式(V)的氯甲酸酯反应,
R2-M-CO-Cl (V)
其中
R2和M具有前面提到的定义。
10.农药组合物,其特征在于包括至少一种权利要求1的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物。
11.权利要求1的式(I)的1-H-3-芳基-吡咯烷-2,4-二酮衍生物在防治害虫中的应用。
12.防治害虫的方法,其特征在于使权利要求1的式(I)的1-H-3-芳基-吡啶烷-2,4-二酮衍生物作用于害虫和/或它们的环境。
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DE4425617A DE4425617A1 (de) | 1994-01-28 | 1994-07-20 | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
DEP4425617.5 | 1994-07-20 |
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JP2021521151A (ja) | 2018-04-13 | 2021-08-26 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 特定の昆虫を防除するためのテトラミン酸誘導体の使用 |
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WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
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- 1994-07-20 DE DE4425617A patent/DE4425617A1/de not_active Withdrawn
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1995
- 1995-01-16 ES ES95905627T patent/ES2332483T3/es not_active Expired - Lifetime
- 1995-01-16 DE DE59511103T patent/DE59511103D1/de not_active Expired - Lifetime
- 1995-01-16 MX MX9603050A patent/MX9603050A/es unknown
- 1995-01-16 WO PCT/EP1995/000150 patent/WO1995020572A1/de active Application Filing
- 1995-01-16 CA CA002182094A patent/CA2182094A1/en not_active Abandoned
- 1995-01-16 BR BR9506577A patent/BR9506577A/pt not_active IP Right Cessation
- 1995-01-16 EP EP95905627A patent/EP0741700B1/de not_active Expired - Lifetime
- 1995-01-16 JP JP7519860A patent/JPH09508133A/ja active Pending
- 1995-01-16 CN CN95191816A patent/CN1080258C/zh not_active Expired - Fee Related
- 1995-01-16 AU AU14166/95A patent/AU695700B2/en not_active Ceased
-
1997
- 1997-11-05 US US08/967,254 patent/US6472419B1/en not_active Expired - Fee Related
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2002
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EP0456063A2 (de) * | 1990-05-10 | 1991-11-13 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
EP0521334A1 (de) * | 1991-06-28 | 1993-01-07 | Bayer Ag | Substituierte 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
Also Published As
Publication number | Publication date |
---|---|
US20040019061A1 (en) | 2004-01-29 |
EP0741700B1 (de) | 2009-10-07 |
EP0741700A1 (de) | 1996-11-13 |
DE4425617A1 (de) | 1995-08-03 |
ES2332483T3 (es) | 2010-02-05 |
JPH09508133A (ja) | 1997-08-19 |
BR9506577A (pt) | 1997-09-23 |
CN1142225A (zh) | 1997-02-05 |
US6472419B1 (en) | 2002-10-29 |
US6939888B2 (en) | 2005-09-06 |
DE59511103D1 (de) | 2009-11-19 |
CA2182094A1 (en) | 1995-08-03 |
AU695700B2 (en) | 1998-08-20 |
MX9603050A (es) | 1997-03-29 |
WO1995020572A1 (de) | 1995-08-03 |
AU1416695A (en) | 1995-08-15 |
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