CN1326439A - 苯基取代的环状烯胺酮类化合物 - Google Patents
苯基取代的环状烯胺酮类化合物 Download PDFInfo
- Publication number
- CN1326439A CN1326439A CN99813208A CN99813208A CN1326439A CN 1326439 A CN1326439 A CN 1326439A CN 99813208 A CN99813208 A CN 99813208A CN 99813208 A CN99813208 A CN 99813208A CN 1326439 A CN1326439 A CN 1326439A
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- Prior art keywords
- alkyl
- group
- phenyl
- expression
- randomly
- Prior art date
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- 125000004122 cyclic group Chemical class 0.000 title abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 79
- 150000001875 compounds Chemical class 0.000 claims description 207
- -1 phenylalkyl oxygen Chemical compound 0.000 claims description 201
- 239000011737 fluorine Substances 0.000 claims description 84
- 229910052731 fluorine Inorganic materials 0.000 claims description 84
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 79
- 239000000460 chlorine Substances 0.000 claims description 79
- 229910052801 chlorine Inorganic materials 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 76
- 239000001257 hydrogen Substances 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 229910052760 oxygen Inorganic materials 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 67
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 61
- 239000001301 oxygen Substances 0.000 claims description 61
- 238000002360 preparation method Methods 0.000 claims description 57
- 239000002585 base Substances 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 53
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 52
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 49
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 48
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
- 239000005864 Sulphur Chemical group 0.000 claims description 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 33
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 31
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 28
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 239000003513 alkali Substances 0.000 claims description 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000005336 allyloxy group Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 241000790917 Dioxys <bee> Species 0.000 claims description 5
- 241000607479 Yersinia pestis Species 0.000 claims description 5
- VAKKJWXZRREDEX-UHFFFAOYSA-N [O].CC#CC Chemical compound [O].CC#CC VAKKJWXZRREDEX-UHFFFAOYSA-N 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 5
- 229920002554 vinyl polymer Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 4
- 125000006606 n-butoxy group Chemical group 0.000 claims description 4
- 150000003053 piperidines Chemical class 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- 125000005920 sec-butoxy group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 150000003624 transition metals Chemical group 0.000 claims description 3
- 238000009333 weeding Methods 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 239000010970 precious metal Substances 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 38
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 229910052727 yttrium Inorganic materials 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 86
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 68
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 50
- 241000196324 Embryophyta Species 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 44
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 239000000463 material Substances 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-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
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
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- 229940036248 turpentine Drugs 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 210000002700 urine Anatomy 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
- 238000005406 washing Methods 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
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/20—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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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/04—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with only hydrogen atoms, halogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- E—FIXED CONSTRUCTIONS
- E04—BUILDING
- E04B—GENERAL BUILDING CONSTRUCTIONS; WALLS, e.g. PARTITIONS; ROOFS; FLOORS; CEILINGS; INSULATION OR OTHER PROTECTION OF BUILDINGS
- E04B1/00—Constructions in general; Structures which are not restricted either to walls, e.g. partitions, or floors or ceilings or roofs
- E04B1/02—Structures consisting primarily of load-supporting, block-shaped, or slab-shaped elements
- E04B1/04—Structures consisting primarily of load-supporting, block-shaped, or slab-shaped elements the elements consisting of concrete, e.g. reinforced concrete, or other stone-like material
- E04B1/043—Connections specially adapted therefor
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- Organic Chemistry (AREA)
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- Structural Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
Abstract
本发明涉及新的式(Ⅰ)的其中Ar、X、Z、Y、K、n和m各如说明书中所定义的苯基取代的环状烯胺醇、它们的多种制备方法、制备它们的中间体及其它们作为除草剂和杀虫剂的应用。
Description
本发明涉及新颖的苯基取代的环状烯胺酮类化合物、其多种制备方法、其中间体及其作为作物保护剂,特别是除草剂、杀螨剂、杀线虫剂和杀虫剂的应用。
某些在苯基环上被取代了的环状烯胺酮化合物已经作为抗菌的喹诺酮的中间体被公开了(R.G.Glushkov,N.B.Marchenko,A.N.Padeiskaya,L.D.Shipilova,Pharm.Chem.J.(Engl.Transl.)24,460-465(1990))。此外,在苯基环上没有被取代的环状烯胺酮化合物也已有公开(M.V.Mezentseva,A.V.Kadushkin,L.M.Alekseeva,A.S.Sokolova,V.G.Granik,Pharm.Chem.J.(Engl.Transl.)25,858-864(1991);G.M.Coppola,R.Damon,A.D.Kahle,M.J.Shapiro,J.Org.Chem.,46,1221-1222(1981);D.Brillon,G.Sauvé,J.Org.Chem.,55,2246-2249(1990))。这些化合物作为作物保护剂的用途尚未被描述过。
K表示氧或硫,
Ar表示各被取代的苯基、萘基或表示各任选被取代的具有5-10个环原子的单或双环杂芳基,
Y表示卤素或各任选被取代的烷基、烷氧基、苯基、苯基烷基、杂芳基、杂芳基烷基或表示下式基团:—CO2R1或
或两个相邻的Yn还表示任选被取代的饱和或不饱和的环,该环可以任选地被杂原子间断,和
Z表示氢,表示各任选被取代的烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、苯氧基烷基、苯基烷基氧基烷基、苯基硫基烷基、苯基烷基硫基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或表示下列各式基团:—CO2R1;
—SO2R1;—COR1;或氰基,
l表示0-3,
m表示1-3,
n取决于m,可以表示0-4,
R1表示氢,表示各任选被取代的、饱和或不饱和的烷基或环烷基,其各任选地被杂原子间断,表示各任选被取代的苯基或杂芳基,表示各任选被取代的苯基烷基或杂芳基烷基,
R2表示氢,表示各任选被取代的、饱和或不饱和的烷基或烷氧基,表示各任选被取代的苯基、苯基烷基或苯基烷氧基,或
R1、R2和它们所连的氮原子一起还可以表示任选被取代的环,该环任选地被杂原子间断,
R3表示氢,表示各任选被取代的烷基或烷氧基,表示各任选被取代的苯基或苯基烷基,
下列定义适用于式(I)化合物:
Ar优选表示Ar1,其中Ar1表示苯基、萘基或具有5-10个环原子的单或双环杂芳基,这些基团各任选地被下列基团一至五取代:卤素、C1-C8-烷基、C2-C8-链烯基、C2-C8-炔基、C1-C8-烷氧基、C2-C8-链烯氧基、C3-C8-炔基氧基、C1-C8-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C8-卤代链烯氧基、C1-C2-亚烷基二氧基、C1-C2-卤代亚烷基二氧基、卤代-C1-C4-烷硫基、卤代-C1-C4-烷基亚磺酰基、卤代-C1-C4-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团:a)-L-CO-R7, 或表示Ar2,其中Ar2表示额外被苯基、萘基、五或六元杂芳基、苯基-C1-C4-烷基、苯氧基、苯基-S(O)g-、五或六元杂芳氧基或杂芳基-S(O)g-取代的Ar1,其中这些取代基本身各自任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基一至四取代。
K优选表示氧或硫。
L优选表示氧或硫。
Y优选表示卤素、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基,表示苯基、苯基-C1-C4-烷基、五或六元杂芳基或五或六元杂芳基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,或表示下式基团:—CO2R1或
两个相邻的Yn还优选表示五至八元的、饱和或不饱和的环,该环可以被1-3个选自N、O和S的杂原子间断并且可以任选地被卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至三取代。
Z优选表示氢,表示各任选被氟和/或氯取代的C1-C8-烷基、氰基-C1-C6-烷基、C3-C8-链烯基、C3-C8-炔基、C3-C8-环烷基、C3-C8-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷氧基-C1-C4-烷基,表示苯氧基-C1-C4-烷基、苯基-C1-C4-烷氧基-C1-C4-烷基、苯硫基-C1-C4-烷基、苯基-C1-C4-烷硫基-C1-C4-烷基、苯基、苯基-C1-C4-烷基、五或六元杂芳基、五或六元杂芳基-C1-C4-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基一至四取代,或表示下列各式基团:—CO2R1;
—SO2R1;—COR1;或氰基,其中
g优选表示0-2,
l优选表示0-2,
R1优选表示氢(但不适用于基团-CO2R1和-SO2R1),表示各任选被氟和/或氯取代的C1-C10-烷基、C2-C10-链烯基、C3-C6-炔基,表示各任选被氟、氯、C1-C4-烷基、C1-C4-烷氧基取代的C3-C8-环烷基或C5-C8-环烯基,其中任选地一个亚甲基可以被氧或硫间断,或表示苯基、吡啶基、噻吩基、嘧啶基、噻唑基、苯基-C1-C4-烷基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R2优选表示氢,表示各任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-链烯氧基,或表示苯基、苯基-C1-C4-烷基或苯基-C1-C4-烷氧基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R1、R2和它们所连的氮原子一起还优选表示各任选被C1-C4-烷基取代的五至八元环,其中任选地一个亚甲基可以被氧或硫替代,
R3优选表示氢,任选被卤素取代的C1-C6-烷基,或表示苯基或苯基C1-C2-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R4优选表示氢或C1-C6-烷基,
R5、R6相互独立地表示氢或表示任选被氟和/或氯取代的C1-C4-烷基,
R7优选表示各任选被氟和/或氯取代的C1-C10-烷基、C2-C10-链烯基、C3-C10-炔基、C1-C10-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷硫基-C1-C4-烷基,表示各任选被氟和/或氯、C1-C4-烷基、C1-C4-烷氧基取代的C3-C8-环烷基或C3-C8-环烷氧基,其中任选地一个亚甲基可以被氧或硫替代,或表示苯基、苯氧基、苄氧基、五或六元杂芳基或苯基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R8优选表示氢或C1-C4-烷基,
R9优选表示氢,各任选被氟和/或氯取代的C1-C10-烷基、C3-C8-链烯基、C3-C8-炔基、C1-C10-烷氧基、C3-C8-链烯氧基,任选地被氟、氯、C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基,其中任选地一个亚甲基可以被氧或硫替代,或表示苯基、苯基-C1-C4-烷基或苯基-C1-C2-烷氧基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R10优选表示氢、C1-C6-烷基或C3-C6-链烯基,
R9、R10和它们所连的氮原子一起还优选表示任选地被C1-C4-烷基取代的五至八元环,其中任选地一个亚甲基可以被氧或硫替代。
m优选表示1-3。
n取决于m,优选表示0-3。
K特别优选表示氧或硫。
Ar特别优选表示Ar1,其中Ar1表示苯基、萘基、喹啉基、噻吩基、嘧啶基、呋喃基、噻唑基、苯并噻唑基、噁唑基、吡唑基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C3-C6-链烯氧基、C3-C6-炔基氧基、C1-C6-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯氧基、C1-C2-亚烷基二氧基、C1-C2-卤代亚烷基二氧基、卤代-C1-C2-烷硫基、卤代-C1-C2-烷基亚磺酰基、卤代-C1-C2-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团之一:a)—L—COR7,
或表示Ar2,其中Ar2表示额外被苯基、吡啶基、嘧啶基、噻吩基、呋喃基、噻唑基、四唑基、三唑基、苄基、苯氧基、苯基-S(O)g-、吡啶基氧基、嘧啶基氧基、噻唑基氧基、吡啶基-S(O)g-、嘧啶基-S(O)g-或噻唑基-S(O)g-取代的Ar1,其中这些取代基本身任选被氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基一至三取代,其中g表示0-2。
L特别优选表示氧或硫。
Y特别优选表示氟、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基,表示苯基、苯基-C1-C2-烷基、噻唑基甲基、吡啶基甲基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至三取代,或表示下式基团:—CO2R1或
两个相邻的Yn还可以特别优选表示五至六元的、饱和或不饱和的环,该环可以被选自N、O和S的杂原子间断并且可以任选地被氟、氯、溴、甲基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一或二取代。
Z特别优选表示氢,表示各任选被氟和/或氯取代的C1-C6-烷基、氰基-C1-C3-烷基、C3-C6-链烯基、C3-C8-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-卤代烷氧基-C1-C2-烷基,表示苯氧基-C1-C2-烷基、苯基-C1-C2-烷氧基-C1-C2-烷基、苯硫基-C1-C2-烷基、苯基-C1-C2-烷硫基-C1-C2-烷基、苯基-C1-C2-烷基、苯基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基一至三取代,或表示下列各式基团:—CO2R1 —SO2R1;—COR1;或氰基,其中
l特别优选表示0-1,
R1特别优选表示氢(但不适用于基团-CO2R1和-SO2R1),表示各任选被氟和/或氯取代的C1-C6-烷基、C2-C6-链烯基、C3-C4-炔基,表示任选被氟、氯、C1-C2-烷基、C1-C2-烷氧基取代的C3-C6-环烷基,或表示苯基或苄基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至二取代,
R2特别优选表示氢,表示各任选被氟和/或氯取代的C1-C4-烷基、C3-C4-链烯基、C3-C4-炔基、C1-C4-烷氧基、C3-C4-链烯氧基,或表示苯基、苄基或苄氧基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至二取代,
R1、R2和它们所连的氮原子一起还特别优选表示任选被C1-C2-烷基取代的五或六元环,其中任选地一个亚甲基可以被氧替代,
R3特别优选表示氢,表示C1-C4-烷基,或表示苯基或苄基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,
R4、R5、R6各特别优选表示氢、甲基或乙基,
R7特别优选表示各任选被氟和/或氯取代的C1-C6-烷基、C2-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-烷硫基-C1-C2-烷基,表示各任选被氟和/或氯、C1-C2-烷基、C1-C2-烷氧基取代的C3-C6-环烷基或C3-C6-环烷氧基,其中任选地一个亚甲基可以被氧替代,或表示苯基、苯氧基、苄氧基、噻吩基、呋喃基、吡啶基、嘧啶基、噻唑基、吡唑基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R8特别优选表示氢,
R9特别优选表示氢,各任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-环烷基,其中任选地一个亚甲基可以被氧替代,或表示苯基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,
R10特别优选表示氢或C1-C4-烷基,
R9、R10和它们所连的氮原子一起还特别优选表示任选地被C1-C2-烷基取代的五至六元环,其中任选地一个亚甲基可以被氧替代,
m特别优选表示1-3。
n取决于m,特别优选表示0-2。
K非常特别优选表示氧或硫。
Ar非常特别优选表示Ar1,其中Ar1表示苯基、噻吩基、嘧啶基、呋喃基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、烯丙氧基、甲基烯丙氧基、2-丁烯氧基、炔丙氧基、2-丁炔氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团之一:a)—L—CO-R7,
d)NHSO2R7,或表示Ar2,其中Ar2表示额外被苯基、吡啶基、噻吩基、四唑基、三唑基或苯氧基取代的Ar1,其中这些取代基本身任选被氟、氯、溴、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、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基一至二取代,和
L非常特别优选表示氧或硫。
Y非常特别优选表示甲基,表示苯基,它任选被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基一至三取代,或表示基团-CO2R1,或
两个相邻的Yn还可以非常特别优选表示六元的不饱和的环,该环可以任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基单取代,
Z非常特别优选表示氢、甲基、乙基、烯丙基、炔丙基、环丙基、环戊基、环己基、环丙基甲基、环戊基甲基、环己基甲基、甲氧基甲基、乙氧基甲基,表示苯基、苄基、吡啶基甲基、噻唑基甲基,它们各任选地被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基、硝基或氰基一至二取代,或表示下列各式基团:—CO2R1,
—SO2R1,—CO—R1,或氰基,其中
R1非常特别优选表示氢(但不适用于基团-CO2R1和-SO2R1)、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、炔丙基、环丙基、环戊基、环己基,或表示苯基或苄基,它们各任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,
R2非常特别优选表示氢、甲基、乙基、丙基、异丙基、烯丙基、炔丙基、甲氧基、乙氧基、烯丙氧基,或表示苄氧基,它任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,或
R1、R2和它们所连的氮原子一起还非常特别优选表示吡咯烷、噻嗪、哌啶或吗啉基团,
R3、R5各非常特别优选表示氢、甲基或乙基,
R7非常特别优选表示甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、乙烯基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、环丙基、环戊基、环己基、环戊基氧基、环己基氧基,表示苯基、吡啶基或苄基,它们各任选被氟、氯、溴、甲基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R9非常特别优选表示氢、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基、环戊基、环己基,表示苯基,它任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,
R10非常特别优选表示氢、甲基或乙基,或
R9、R10和它们所连的氮原子一起还非常特别优选表示吡咯烷、哌啶或吗啉基团。
m非常特别优选表示1-3。
n取决于m,非常特别优选表示0-1。
K尤其优选表示氧或硫。
Ar尤其优选表示Ar1,其中Ar1表示苯基、噻吩基、嘧啶基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、烯丙氧基、甲基烯丙氧基、2-丁烯氧基、炔丙氧基、2-丁炔氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、硝基、巯基、氰基、氨基,
或表示Ar2,其中Ar2表示额外被苯基或苯氧基取代的Ar1,其中这些取代基本身任选被氟、氯、溴、甲基、乙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基一至二取代。
X尤其优选表示CN。
Z尤其优选表示氢或甲基。
m尤其优选表示1-3。
n尤其优选表示0。
所有上面所列的式(I)的化合物都可以以顺式-和反式-异构体存在。为了简化表述,在对各式表示的化合物中每种情况下仅给出一种异构体。然而,本发明也包括其各自的另一种异构体。
上面提到的一般或优选的基团定义适合于式(I)的终产物,也相应地适合于各制备所需要的前体或中间体。这些基团的定义可以按需要相互组合,即,包括给定的优选范围间的组合。
本发明优选的是含有上文列出的优选含义组合的式(I)化合物。
本发明特别优选的是含有上文列出的特别优选含义组合的式(I)化合物。
本发明非常特别优选的是含有上文列出的非常特别优选含义组合的式(I)化合物。
本发明尤其优选的是含有上文列出的尤其优选含义组合的式(I)化合物。
饱和或不饱和烃基如烷基或链烯基,也包括与杂原子的组合,例如在烷氧基中,在每一种情况下,只要可能,均可以是直链或支链的。
除非另有说明,否则,任选取代的基团可以单-或多取代,且在多取代的情况下,取代基可以相同或不同。
本发明式(I)化合物的实例列于下列各组中:组1:(Q)p(p=1-3)在此具有例如下面所列的意义:氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、烯丙氧基、甲基烯丙氧基、2-丁烯氧基、炔丙氧基、2-丁炔氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、巯基、硝基、氰基、氨基。组2:Q和p在此具有例如在组1下给出的意义。
Q和p在此具有例如在组1下给出的意义(但是p=0-2)。组6:
Q和p在此具有例如在组1下给出的意义(但是p=0-2)。组8:
Q和p在此具有例如在组1下给出的意义(但是p=0-2)。
业已发现,新的式(I)化合物通过下文描述的方法获得:
Ar、X、Y、m、n各如上所定义,
K表示氧,和
Y、m、n各如上所定义,
W表示O或S(O)g,其中g表示0或2,和
R11表示烷基,特别是表示C1-C6-烷基,或苄基,该反应任选地在稀释剂存在下和任选地在碱或酸和/或下式(IIIa)的金属化合物存在下进行,
Me(V)2 (IIIa)其中
Me表示二价过渡金属原子,特别是镍,和
V表示螯合物配位体,特别是有二齿的螯合物配位体,诸如乙酰丙酮化物(R.G.Glushkov等人,Khim.-Farm.Zh.24,(7),(1990),24-27;M.V.Mezentseva等人,Khim.-Farm.Zh.25,(12),(1991),19-23;G.Dannhardt,A.Bauer,Pharmazie 51,(1996),805-810)。
B)此外,已经发现,下列式(I)化合物其中
Ar、Y、X、m、n各如上所定义,
K表示氧,和
Ar和X各如上所定义,和
Hal表示卤素,特别是氯或溴,其中
Y、m和n各如上所定义,得到式(VI)化合物,其中
Ar、X、Y、m和n各如上所定义,
该化合物进一步任选地在碱存在下和任选地在三价磷化合物(例如三苯基膦、亚磷酸三乙酯)存在下进行反应消除硫和卤化氢,得到其中Ar、X、Y、m和n各如上所定义和Z表示氢的式(I)化合物(参见A.Eschenmoser等人,Helv.Chim.Acta 54,(1971),710-734;V.Issartel等人,C.R.Acad.Sci.,Ser.II,Mec.,Phys.Chim.,Astron.321,(12),(1995),521-524)。C)此外,现已发现,下列式(I)化合物其中
Ar、Z、X、Y、m和n各具有上述给出的意义之一,
K表示氧,和
Y、Z、m和n各具有上述给出的意义之一,和
Y、Z、m和n各具有上述给出的意义之一,
Z不是氢,和
Hal代表卤素,特别是氯或溴,然后该化合物与式(II)化合物任选地在稀释剂存在下和任选地在酸受体存在下反应(参见G.Dannhardt,A.Bauer,Pharmazie 51,(1996),805-810),其中
Ar、X各如上所定义。
D)此外,已经发现,下列式(I)化合物其中
Ar、Z、X、Y、m和n各具有上述给出的意义之一,
K表示氧,但是
Ar、X、Y、m和n各如上所定义,
Z-G (IX),其中
G表示离去基团诸如卤素,特别是碘、溴、氯,磺酸酯基例如甲磺酸酯基、三氟甲磺酸酯基或甲苯磺酸酯基,或烷氧基。
Ar2、X、Y、Z、m和n各如上所定义,和
Ar1、X、Y、Z、m和n各如上所定义,和
Hal表示卤素,特别是溴,
Ar2—B(OH)2 (X),其中
Ar2’表示上述在Ar2下作为Ar1的额外的取代基已经提及的取代基。
F)此外,已经发现,下列式(I)化合物其中
Ar、X、Y、Z、m和n各如上所定义,和
K表示硫,可以如下获得:在硫化剂诸如五硫化磷或2,4-二(4-甲氧基苯基)-1,2,3,4-二硫杂磷烷-2,4-二硫化物(Lawesson’s试剂)存在下在溶剂存在下使定义如下的式(I)化合物反应,其中
Ar、X、Y、Z、m和n各如上所定义,和
K表示氧。
根据方法C,使用,例如,3,4-二氯苯甲酰基乙腈和N-甲基吡咯烷酮作为起始原料,该反应可以用下述反应式来表示:
根据方法D,使用,例如,3-氧代-2-吡咯烷-2-亚基-3-(4-三氟甲氧基苯基)丙腈和2-氯-5-氯甲基吡啶作为起始原料,该反应可以用下述反应式来表示:
根据方法E,使用,例如,3-氧代-2-吡啶-2-亚基-3-(4-溴苯基)丙腈和4-氯苯基硼酸作为起始原料,该反应可以用下述反应式来表示:根据方法F,使用,例如,3-氧代-2-吡咯烷-3-(4-氯苯基)丙腈作为起始原料和Lawesson’s试剂,该反应可以用下述反应式来表示:
在方法(A)中需要用作起始原料的式(II)化合物中有一些是新的并且可以通过原则上从文献(Organikum,第16修改版,pp.415,417,VEBDeutscher Verlag der Wissenschaften,Berlin 1986)中已知的方法制备,其中
Ar、X各如上所定义。
式(II)化合物中,下列化合物特别适用于制备新的农药、特别是杀螨、除草和杀虫终产物:
式(II-1-b)的新化合物,其中T如下表中所定义:
化合物编号 | T | M.p.℃ |
II-1-b-1 | 3-Cl,4-F | 78 |
II-1-b-2 | 4-Cl,3-F | 87 |
II-1-b-3 | 3,5-(CF3)2 | 91 |
II-1-b-4 | 2,4-Cl2,5-F | 106 |
II-1-b-5 | 3,5-Cl2,4-F | 138-140 |
II-1-b-6 | 4-Cl,2-F | 90-94 |
II-1-b-7 | 3-CF3,5-CH3 | 92 |
II-1-b-8 | 3-Cl,4,5-F2 | 84-88 |
II-1-b-9 | 4-CN,2,5-F2 | 107-108 |
II-1-b-10 | 2,3-F2 | 74 |
II-1-b-11 | 3-F,4-CF3 | 92 |
II-1-b-12 | 3,4-O-CF2-O | 70-73 |
II-1-b-13 | 3-NO2,5-CF3 | |
II-1-b-14 | 4-Cl,2,5-F2 | 116 |
化合物编号 | T | M.p.℃ |
II-1-b-15 | 3,4,5-(OC2H5)3 | 122 |
II-1-b-16 | 4-Br,2-F | 118 |
II-1-b-17 | 2,6-Cl2,4-CF3 | 123 |
II-1-b-18 | 2-F,4-NO2 | 168 |
II-1-b-19 | 2,4-Cl2,5-NO2 | 100 |
II-l-b-20 | 4-Cl,2-F,5-NO2 | 118 |
II-1-b-21 | 2,4-F2,5-NO2 | 128 |
II-1-b-22 | 4-Br,2-F,5-NO2 | 141 |
II-1-b-23 | 2-F,4-CF3 | 62 |
II-1-b-24 | 4-OCF3,3-NO2 | 95 |
II-1-b-25 | 4-Cl,2-NO2 | 130 |
II-1-b-26 | 2-F,3-CF3 | 67-69 |
II-1-b-27 | 2-Cl,6-F | 46-48 |
II-1-b-28 | 2-Cl,3-CF3 | 90-93 |
II-1-b-29 | 3,4-O-(CF2)2-O- | 206 |
II-1-b-30 | 2-Cl,4-SCH3 | 110 |
II-1-b-31 | 2-Cl,4-SO2CH3 | 202 |
化合物编号 | T | M.p.℃ |
II-2-b-1 | 2,6-Cl2 | >220 |
II-2-b-2 | 2,6-Cl2,4-CH3 | 95 |
II-2-b-3 | 6-Cl | 122 |
化合物编号 | T | M.p.℃ |
II-3-b-1 | 2-CF3,3-(4-Cl′-C6H4) | 油状物 |
II-3-b-2 | 2-CF3,3-(2,4-Cl2′-C6H3) | 油状物 |
Ar如上所定义,
R12表示烷基,特别是C1-C6-烷基,或苄基,它可以任选地被取代,在酸(例如无机酸如盐酸)或碱(例如碱金属氢氧化物如氢氧化钠或氢氧化钾)存在下和任选地在稀释剂(例如含水醇如甲醇或乙醇)存在下在0-200℃、优选20-150℃的温度下水解然后脱羧获得,其中基团R12的除去如果希望的话也可以通过已知方法(Bowman,Fordham,J.Chem.Soc.1951,2758)用分子氢在1-100巴压力下任选地在溶剂例如甲醇、乙醇或乙酸乙酯存在下在-20至100℃的温度、优选室温下在任选地固定在载体例如活性炭或硫酸钡上的过渡金属例如钯、镍、铑或铂存在下氢解来进行。
式(XI)化合物可以通过已知的方法(Organikum,第16修改版,pp.480,VEB Deutscher Verlag der Wissenschaften,Berlin 1986)制备。
式(XI)化合物例如通过在碱(例如碱金属醇盐如甲醇钠或乙醇钠)存在下和任选地在稀释剂(例如醚或由醇盐衍生的醇)存在下在0-150℃、优选20-120℃的温度下使式(XII)化合物与式(XIII)的氰基乙酸酯反应得到,其中
R12表示烷基,特别是C1-C6-烷基。
式(XII)化合物中的一些是新的并且可以通过原则上已知的方法(例如,Organikum,第16修改版,pp.423,VEB Deutscher Verlag derWissenschaften,Berlin 1986)制备。
式(XII)化合物例如通过任选地在稀释剂(例如任选氯代的脂族或芳族烃如甲苯或二氯甲烷)存在下在0-150℃、优选20-100℃的温度下使式(XIV)化合物与卤化剂(例如亚硫酰氯、光气、三氯化磷)反应得到,其中
Ar如上所定义。
式(XIII)的氰基乙酸酯是有机化学中已知的化合物。
Y、R11、m和n各如上所定义,和
W表示氧。
式(III)化合物例如通过任选地在稀释剂存在下在-20至150℃、优选0-100℃的温度下使式(VII)化合物与烷化剂(例如硫酸二甲酯、四氟硼酸三乙基氧鎓(Meerwein盐))反应得到,其中
Y、m和n各如上所定义,和
Z表示氢。
此外,当先在溶剂存在下用硫化剂例如Lawesson’s试剂将式(VII)化合物转化成式(V)的硫代酰胺,随后任选地在碱存在下和在溶剂存在下与式(XV)的烷化剂反应时,得到了作为方法A的起始原料需要的定义如下的式(III)化合物,其中
Y、R11、m和n各如上所定义,和
Y、m和n各如上所定义,和
Y、m和n各如上所定义,和
Z表示氢,
R11—Hal (XV)其中
R11如上所定义,和
Hal表示卤素,特别是碘和溴。
方法(A)的特征在于使其中Ar、X各如上所定义的式(II)化合物与R11、W、Y、m、n各如上所定义的式(III)化合物在稀释剂存在下和任选地在碱存在下反应。
用于方法(A)的合适的稀释剂是对所述的反应物呈惰性的所有有机溶剂。优选使用任选氯代的脂族或芳族烃例如甲苯、二甲苯或二氯甲烷,以及极性溶剂例如二甲基亚砜、二甲基甲酰胺或N-甲基吡咯烷酮。
用于进行方法(A)的合适的碱是所有常规的不水解反应物的酸受体。
优选使用叔胺例如三乙胺、吡啶或N,N-二甲基苯胺。
用于进行方法(A)的合适的酸是所有不水解反应物的酸。优选使用有机酸例如对甲苯磺酸和三氟乙酸。
当进行本发明方法(A)时,反应温度可以在较宽的范围内变化。有利的是,反应是在-20℃至160℃,优选在0℃至120℃的温度下进行。
方法(A)优选在大气压下进行。
当进行本发明方法(A)时,基于式(II)的反应组分,式(III)的反应组分以等摩尔量或较大过量(最多5mol)、优选1.5-2倍摩尔量使用。
任选使用的碱优选以与式(II)的反应组分等摩尔量使用。任选使用的酸优选以催化量使用。
方法(B)的特征在于使式(IV)化合物各与式(V)的硫代酰胺任选地在稀释剂存在下和任选地在酸结合剂存在下反应。
式(IV)起始原料可以通过已知方法(Gakhar H.K.等人,J.IndianChem.Soc.43,(1971),953或Corsaro A.,Heterocycles 23,(1985),2645)制备。式(V)化合物可以用亚硫酰化试剂、特别是Lawesson’s试剂在惰性溶剂如甲苯中从相应的酮化合物制备(参见制备实施例9)。除了5-苯基吡咯烷-2-硫酮(参见Lettau等人,PHARAT,Pharmazie48,(1993)410)和5-(3,4-二甲氧基苯基)吡咯烷-2-硫酮外,式(V)的取代的5-苯基吡咯烷-2-硫酮和6-苯基哌啶-2-硫酮都是新的。
合适的进行本发明方法B)的稀释剂是所有对式(IV)化合物呈惰性的溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类例如丙酮和甲基异丙基酮,此外还有醚类例如乙醚、四氢呋喃和二噁烷,还有羧酸酯类例如乙酸乙酯,以及强极性溶剂例如二甲基甲酰胺、N-甲基吡咯烷酮、二甲基亚砜和环丁砜。
合适的进行本发明方法B)的酸结合剂是所有常规的酸结合剂。优选使用叔胺例如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,聚合的碱例如二异丙基氨基聚苯乙烯,还有碱土金属氧化物例如氧化镁和氧化钙,还有碱金属和碱土金属的碳酸盐例如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物例如氢氧化钠和氢氧化钾。
用于进行本发明方法(B)的合适的磷试剂是亚磷酸烷基酯例如亚磷酸三乙酯、亚磷酸三丁酯,或三苯基膦类例如三苯基膦。
当进行本发明方法(B)时,反应温度可以在较宽的范围内变化。通常,反应是在0℃至200℃、优选+20℃至150℃的温度下进行。
当进行本发明方法(B)时,式(IV)的起始原料和式(V)的硫代酰胺一般各以大约当量量使用。然而,也可以较大过量地使用一种或另一种组分。后处理通过常规方法进行。
方法(C)的特征在于,任选地在稀释剂存在下,使式(VII)化合物与卤化剂如光气、二光气、三光气反应,得到式(VIII)化合物,然后该化合物与式(II)化合物任选地在酸结合剂存在下和任选地在稀释剂存在下反应。一些式(VII)起始原料例如N-甲基吡咯烷酮是市售的或它们可以通过已知方法制备。
合适的进行本发明方法(C)的反应的酸结合剂是所有常规的酸受体。优选使用叔胺例如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,聚合的碱例如二异丙基氨基聚苯乙烯,还有碱土金属氧化物例如氧化镁和氧化钙,还有碱金属和碱土金属的碳酸盐例如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物例如氢氧化钠和氢氧化钾。
合适的进行本发明方法(C)的稀释剂是所有对卤化剂呈惰性的溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类例如丙酮和甲基异丙基酮,此外还有醚类例如乙醚、四氢呋喃和二噁烷,还有羧酸酯类例如乙酸乙酯,还有腈类例如乙腈,以及强极性溶剂例如二甲基亚砜和环丁砜。
当进行本发明方法(C)时,反应温度可以在较宽的范围内变化。通常,反应是在-20℃至100℃、优选0℃至80℃的温度下进行。
本发明方法(C)一般在常压下进行。
当进行本发明方法(C)时,式(VII)的起始原料和适当的卤化剂一般在每种情况下以大约等当量的量使用。然而,也可以较大过量地(最多3mol)使用一种或另一种组分。后处理通过常规方法进行。通常,除去沉淀的盐,然后将剩下的反应混合物通过汽提掉溶剂而浓缩。
方法(D)的特征在于,任选地在稀释剂存在下和任选地在酸结合剂存在下,使其中Ar、X、Y、m和n各如上所定义而Z表示氢的式(I)化合物各与式(IX)的烷化剂、酰化剂、磺酰化剂或缩合剂反应。
所用的式(IX)的烷化剂、酰化剂、磺酰化剂或缩合剂是已知的有机化学中的合成化学品。
合适的进行本发明方法(D)的稀释剂是所有对上述试剂呈惰性的溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类例如二氯甲烷、氯仿、四氯化碳、氯苯和邻二氯苯,还有酮类例如丙酮和甲基异丙基酮,此外还有醚类例如乙醚、四氢呋喃和二噁烷,还有羧酸酯类例如乙酸乙酯,以及强极性溶剂例如二甲基亚砜、二甲基甲酰胺、N-甲基吡咯烷酮和环丁砜。如果酰化剂和磺酰化剂的水解稳定性许可的话,反应也可以在水存在下进行。
合适的进行本发明方法(D)的反应的酸结合剂是所有常规的酸受体。优选使用叔胺例如三乙胺、吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)、二氮杂二环壬烯(DBN)、Hünig碱和N,N-二甲基苯胺,还有碱土金属氧化物例如氧化镁和氧化钙,还有碱金属和碱土金属的碳酸盐例如碳酸钠、碳酸钾和碳酸钙,以及还有碱金属氢氧化物例如氢氧化钠和氢氧化钾,以及还有碱金属氢化物例如氢化钠、氢化钾,或碱金属醇盐例如叔丁醇钾。
当进行本发明方法(D)时,反应温度可以在较宽的范围内变化。通常,反应是在-70℃至+150℃、优选-20℃至100℃的温度下进行。
当进行本发明方法(D)时,上述式(I)的起始原料和上述的式(IX)的试剂一般各以大约等当量的量使用。然而,也可以较大过量地(最多5mol)使用上述试剂。后处理通过常规方法进行。
优选的进行本发明方法(E)的催化剂是钯(O)配合物。优选例如四(三苯基膦)钯。
进行方法(E)所需要的芳基硼酸中的一些是市售的例如4-氯苯基硼酸,或者它们可以通过已知方法制备。
合适的进行本发明方法(E)的酸受体是无机或有机碱。这些碱优选包括碱土金属或碱金属的氢氧化物、乙酸盐、碳酸盐或碳酸氢盐,如氢氧化钠、氢氧化钾、氢氧化钡或氢氧化铵、乙酸钠、乙酸钾、乙酸钙或乙酸铵、碳酸钠、碳酸钾或碳酸铵、碳酸氢钠或碳酸氢钾,碱金属氟化物例如氟化铯,以及叔胺类,如三甲胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、N-甲基哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环十一碳烯(DBU)或二氮杂二环壬烯(DBN)。
合适的进行本发明方法(E)的稀释剂是水、有机溶剂及其任意混合物。可提及的实例包括:脂族、脂环族或芳族的烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或四氢化萘;卤代烃,如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷、三氯乙烷或四氯乙烯;醚类,如乙醚、异丙醚、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、二甘醇二甲醚或苯甲醚;醇类,如甲醇、乙醇、正或异丙醇、正-、异-、仲-或叔丁醇、乙二醇、丙-1,2-二醇、乙氧基乙醇、甲氧基乙醇、二甘醇单甲醚、二甘醇单乙醚;水。
当进行本发明方法(E)时,反应温度可以在较宽的范围内变化。通常,反应是在0℃至+140℃、优选50℃至+100℃的温度下进行。
当进行本发明方法(E)时,其中Ar2’如上所定义的式(X)的硼酸和其中Ar1、X、Y、Z、m、n和Hal各如上所定义的式(I1)化合物以1∶1至3∶1、优选1∶1至2∶1的摩尔比使用。通常,每摩尔的式(I1)化合物使用0.005-0.5摩尔、优选0.01-0.1摩尔的催化剂。碱通常过量使用。
方法(F)的特征在于,任选地在稀释剂存在下,使其中Ar、X、Y、Z、m和n各如上所定义而K表示氧的式(I)化合物与硫化剂反应。
所用的硫化剂是用于合成的已知化学品例如五硫化磷或2,4-二(4-甲氧基苯基)-1,2,3,4-二硫杂磷烷-2,4-二硫化物(Lawesson’s试剂)。
合适的进行本发明方法(F)的稀释剂是所有对上述试剂呈惰性的溶剂。优选使用烃类例如汽油、苯、甲苯、二甲苯和四氢化萘,还有卤代烃类例如二氯甲烷、氯仿、氯苯和邻二氯苯,醚类例如四氢呋喃、二噁烷、异丙醚或甲基叔丁基醚。
当进行本发明方法(F)时,反应温度可以在较宽的范围内变化。通常,反应是在0℃至250℃、优选40℃至200℃的温度下进行。
当进行本发明方法(F)时,上述式(I)的起始原料和上述试剂一般各以大约等当量的量使用。然而,也可以较大过量地(最多5mol)使用上述试剂。后处理通过常规方法进行。
本发明活性化合物特别适用于作为脱叶剂、干燥剂、杀茎杆剂和尤其是用作除杂草剂。所谓的杂草,就其最广义而言,应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
防治杂草所需要的本发明活性化合物的剂量为0.001-10kg/ha,优选0.005-5kg/ha。
本发明活性化合物可以与例如下列植物相关使用:
下列属的双子叶杂草:苘麻属、苋属、豚草属、Anoda、春黄菊属、Aphanes、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、藜属、蓟属、旋花属、曼陀罗属、金钱草属、刺酸模属、糖芥属、大戟属、鼬瓣花属、牛滕菊属、猪殃殃属、木槿属、甘薯属、地肤属、野芝麻属、独行菜属、母草属、母菊属、薄荷属、山靛属、Mullugo、勿忘草属、罂粟属、牵牛属、车前草属、蓼属、马齿苋属、毛茛属、萝卜属、蔊菜属、节节菜属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、白芥属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、遏蓝菜属、三叶草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
下列属的双子叶作物:花生属、甜菜属、芸苔属、黄瓜属、南瓜属、向日葵属、胡萝卜属、大豆属、棉属、甘薯属、莴苣属、亚麻属、蕃茄属、烟草属、菜豆属、豌豆属、茄属、野豌豆属。
下列属的单子叶杂草:山羊草属、冰草属、剪股颖属、看麦娘属、阿披拉草属、燕麦属、臂形草属、雀麦属、蒺藜草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、Eleocheris、蟋蟀草属、画眉草属、野黍属、羊茅属、飘拂草属、Heteranthera、白茅属、鸭嘴草属、千金子属、黑麦草属、雨久花属、稷属、雀稗属、草芦属、梯牧草属、早熟禾属、罗氏草属、慈菇属、藨草属、狗尾草属、高梁属。
下列属的单子叶作物:葱属、凤梨属、天门冬属、燕麦属、大麦属、稻属、黍属、甘蔗属、黑麦属、高梁属、Triticale、、小麦属、玉米属。
根据本发明,可以处理所有植物和部分植物。在这里,植物应理解为所有植物和植物种群诸如想要的和不想要的野生植物或农作物植物(包括天然存在所农作物植物)。农作物植物可以是可以通过常规的育种和优化方法或生物技术和基因工程方法或这些方法的结合获得的植物,包括转基因植物和包括cultivars,其可能被也可能不被植物育种者证书保护。部分植物应理解为是指所有地上和地下部分和植物器官,诸如芽、叶、花和根,可提及的例子有叶子、针叶、茎、树干、花、芽体、果实和种子,以及还有根、块茎和根茎。部分植物还包括收获的植物和植物性的和有生殖力的繁殖材料,例如秧苗、块茎、根茎、切割物和种子。
根据本发明用活性化合物对植物和部分植物的处理是按照常规的处理方法直接进行或通过作用于它们的环境、栖息地或储存领域来进行的,所述常规方法例如有浸渍、喷雾、蒸发、雾化、弥散、刷涂和,在繁殖物的情况下,特别是在种子的情况下,还可以通过一层或多层涂布来处理。
然而,本发明活性化合物的应用决不限于这些属,而是也可以相同的方式延伸至其它植物。在使用本发明活性化合物时,特别强调的是与转基因植物相关的使用,这是因为在这种情况下可以观察到增效的活性增加。
取决于化合物的浓度,化合物适合于灭生性防治杂草,例如工业地域和铁道线,以及有或无种植树林的道路和广场。同样,化合物可以用于防治多年生作物中的杂草,例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明化合物特别适合于以芽前和芽后方式选择性地防治双子叶作物中的单子叶杂草。它们可以非常成功地例如用于防治棉花和甜菜中的有害杂草。
活性化合物可以转化成常规的制剂,如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料,以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产,例如,将活性化合物与扩充剂,即液体溶剂和/或与固体载体混合,并任选地使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
在用水作扩充剂的情况下,也可以用有机溶剂作助溶剂。适合的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物或氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂族烃,如环己烷或石蜡,例如石油馏份、矿物和植物油,醇类,如丁醇或二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺或二甲基亚砜,以及水。
适合的固体载体是:例如铵盐和磨碎的天然矿物质,如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐,适合用于颗粒剂的固体载体有:例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂是: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,烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及白蛋白水解产物;适合的分散剂是:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,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,和合成磷脂。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂,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,和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95%的活性化合物,优选0.5至90%。以及此外还有扩充剂和/或表面活性剂。
本发明活性化合物可以其商业上可得的制剂和由这些制剂制备的使用形式作为与例如如下的其它活性化合物的混合物存在:杀虫剂、引诱剂、不育剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂或除草剂。杀虫剂尤其包括例如磷酸酯类、氨基甲酸酯类、羧酸酯类、氯代烃类、苯基脲类以及由微生物产生的物质。在本发明的优选实施方案中,也可以将安全剂(safener)与本发明的化合物混合以增加作物植物的相容性。
特别有利的混合组分的实例如下:
杀真菌剂:
aldimorph,氨丙磷酸,氨丙磷酸钾盐,andoprim,敌菌灵,戊环唑,azoxystrobin,
苯霜灵,邻碘酰苯胺,苯菌灵,benzamacril,benzamacryl-isobutyl,双丙氨酰磷,乐杀螨,联苯,双苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁赛特,
石硫合剂,capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,carvon,灭螨猛,灭瘟唑,chlorfenazole,地茂散,氯化苦,百菌消,乙菌利,clozylacon,代森盐,霜尿氰,环唑醇,cyprodinil,酯菌胺,
debacarb,双氯酚,苄氯三唑醇,diclofluanid,哒菌清,氯硝胺,乙霉威,噁醚唑,二甲嘧吩,烯酸吗啉,烯唑醇(diniconazole),烯唑醇(diniconazole-M),二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,十二环吗啉,多果定,联氨噁唑酮,
克瘟散,epoxiconazole,乙环唑,乙嘧酚,土菌灵,
famoxadon,咪菌腈,氯苯嘧啶醇,fenbuconazole,甲呋酰苯胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,三苯基醋酸锡,三苯基氢氧化锡,福美铁,嘧菌腙,氟啶胺,flumetover,氟氯菌核利,fluquinconazole,调嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,乙磷钠,四氯苯酞,麦穗宁,呋霜灵,furametpyr,二甲呋酰苯胺,呋菌唑,呋醚唑,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双胍辛醋酸盐(iminoctadine,iminoctadinealbesilate,iminoctadine triacetate),iodocarb,ipconazole,异稻瘟净(IBP),异菌脲,irumamycin,稻瘟灵,isovaledione,
春雷霉素,kresoxim-methyl,铜制剂,例如:氢氧化铜,环烷酸铜,氯氧化铜,硫酸铜,氧化铜,8-羟基喹啉铜和波尔多液,
代森锰铜,代森锰,代森锰锌,meferimzone,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,氯苯咯菌胺,噻菌胺,米多霉素,腈菌唑,甲菌利,
二甲基二硫氨基甲酸镍,nitrothal-isopropyl,氟苯嘧啶醇,
甲呋酰胺,噁霜灵,oxamocarb,喹菌酮,氧化萎锈灵,oxyfenthiin,
稻瘟酯,戊菌唑,戊菌隆,稻瘟磷,四氯苯酞,多马霉素,病花灵,聚氨基甲酸酯,多氧霉素,烯病异噻唑,味鲜安,腐霉利,丙酰胺,propanosine-sodium,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,氯吡呋醚,
quinconazole,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,氟嘧唑,噻菌灵,噻菌腈,thifluzamide,甲基硫菌灵,福美双,tioxymid,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,triazbutil,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
烯效唑,
稻纹散,乙烯菌核利,烯霜苄唑,
zarilamide,代森锌,福美锌,还有
Dagger 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-丙基-1H-1,2,4-三唑-1-乙醇,
α-(2,4-二氯苯基)-β-甲氧基-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)-(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}-氨基甲酸异丙酯,
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-[(二碘代甲基)-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-碳酰苯胺,
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-(甲硫基)-4-嘧啶基-硫代氰酸酯,
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-(2,3,3-三碘代-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-脱氧-4-O-(4-O-甲基-β-D-吡喃葡糖基)-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-(溴代甲基)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-(异硫代氰酰甲基)-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-异噁唑啉基]-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-甲烷胺,
8-羟基喹啉硫酸盐,
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-硫代苯二羧酸酯,
顺-1-(4-氯代苯基)-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-羧酸甲酯,
N-(2,6-二甲基苯基)-N-(5-异噁唑基羰基)-DL-丙氨酸甲酯,
N-(氯代乙酰基)-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-噁唑啉基)-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-[(氯代乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯代-4,5-双(2-丙炔基氧基)-苯基]-N’-甲氧基-甲烷亚氨酰胺,
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,
O-甲基S-苯基苯基丙基硫代氨基磷酸酯,
S-甲基1,2,3-苯并噻二唑-7-硫代甲酸酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃-3’-酮,
杀细菌剂:
bronopol,双氯酚,氯甲基吡啶,二甲基二硫氨基甲酸镍,春雷霉素,异噻唑酮,呋喃羧酸,oxytetracycline,烯异丙噻唑,链霉素,叶枯酞,硫酸铜和其它铜制剂。
杀昆虫剂/杀螨剂/杀线虫剂:
齐墩螨素,乙酰甲胺磷,acetamiprid,氟酯菊酯,棉铃威,涕灭威,氧涕灭威,甲体氯氰菊酯(alpha-cypermethrin,alphamethrin),双虫脒,avermectin,AZ60541,azadifachtin,甲基吡噁磷,azinphos-A,保棉磷,三唑锡,
日本甲虫芽孢杆菌(Bacillus popilliae),球形芽孢杆菌(Bacillus sphaericus),枯草芽孢杆菌(Bacillus subtilis),苏云金芽孢杆菌(Bacillus thuringiensis),baculoviren,蚕白僵菌(Beauveria bassiana),纤细白僵菌(Beauveria tenella),噁虫威,丙硫克百威,杀虫磺,苯螨特,氟氯氰菊酯,bifenazate,氟氯菊酯,bioethanomethrin,生物氯菊酯,BPMC,bromophos A,溴硫磷,合杀威,噻嗪酮,丁酮威,butylpyridaben,
硫线磷,甲萘威,克百威,三硫磷,丁硫百克威,杀螟丹,chloethocarb,chlorethoxyfos,chlorfenapyr,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,chlovaporthrin,顺式-苄呋菊酯,顺式氯菊酯,clocythrin,除线威,四螨嗪,杀螟腈,cycloprene,乙氰菊酯,氟氯氰菊酯-β,cyhalothrin,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,杀螨隆,二嗪磷,敌敌畏,除虫脲,乐果,甲基毒虫畏,diofenolan,乙拌磷,docusat-sodium,dofenapyn,
克瘟散,emamectin,烯炔菊酯,硫丹,entomopfthora spp.,高氰戊菊酯,乙硫苯威,乙硫磷,灭线磷,etofenprox,醚菊酯,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,苯硫威,fenoxacrim,双氧威,氯氰菊酯,fenpyrad,fenpyrithrin,唑螨酯,氰戊菊酯,fipronil,氟定胺,fluazuron,flubrocythrinate,氟螨脲,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,
granulosis viruses,
halofenozide,HCH,庚烯磷,氟铃脲,噻螨酮,烯虫乙酯,
吡虫啉,氯唑磷,异丙胺磷,噁唑磷,ivermectin,
nuclear polyhedrosis viruses,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,methamidophos,metharhiziumanisopliae,metharhizium flavoviride,蜗牛敌,虫螨畏,甲胺磷,杀扑磷,灭梭威,灭多威,速灭威,milbemectin,久效磷,
二溴磷,nitenpyram,nithiazine,novaluron,
氧乐果,杀线威,亚砜吸磷,
玫烟色拟青霉(Paecilomyces fumosoroseus),对硫磷-A,对硫磷-M,氯菊酯,稻丰散,甲拌磷,伏杀硫磷,亚胺硫磷,磷胺,辛硫磷,抗芽威,嘧啶磷-A,嘧啶磷-M,丙溴磷,猛杀威,残杀威,丙硫磷,发果,pymetrozine,吡唑硫磷,pyresmethrin,除虫菊酯,哒螨酮,Pyridathion,pyrimidifen,蚊蝇醚,
喹硫磷,
Ribavirin,
蔬果磷,sebufos,silafluofen,spinosad,治螟硫磷,甲丙硫磷,
氟胺氰菊酯,tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,theta-cypermethrin,thiamethoxam,噻丙腈,thiatriphos,thiocyclamhydrogen oxalate,硫双威,久效磷,thuringiensin,二甲硫吸磷,虫线磷,四溴菊酯,苯噻螨,三唑磷,triazuron,trichlophenidine,敌百虫,杀虫隆,混灭威,
芽灭多,vaniliprole,verticillium lecanii,
YI5302,
zeta-cypermethrin,zolaprofos,
环丙烷羧酸(1R-顺式)-[5-(苯基甲基)-3-呋喃基]-甲基-3-[(二氢-2-氧代-3(2H)-亚呋喃基)-甲基]-2,2-二甲酯,
环丙烷羧酸(3-苯氧基苯基)-甲基-2,2,3,3-四甲酯,
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-氟代苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑,
2-(乙酰氧基)-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]-苯甲酰基,
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)苯基]-氨基]-羰基]-苯甲酰基,
氨基甲酸3-甲基苯基丙酯,
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,
苏云金芽孢杆菌菌株EG-2348,
[2-苯甲酰基-1-(1,1-二甲基乙基)-苯甲酰肼,
丁酸2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4.5]十二烷-3-烯-4-酯,
[3-[(6-氯-3-吡啶基)甲基]-2-亚噻唑烷基]-氨腈,
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-肼二硫代二甲酰胺,
N-甲基-N’-2-丙烯基-1,2-肼二硫代二甲酰胺,
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸酯。
除草剂:
乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、benzobicyclon、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草特、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、灭草平、杀草敏、氯嘧黄隆(乙酯)、草枯醚、氯磺隆、绿麦隆、cinidon(-ethy)、环庚草醚、醚黄隆、clefoxydim、烯草酮、炔草酸、异噁草松、氯甲酰草胺、二氟吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟酰草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、异戊净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、dymron、epoprodan、茵草敌、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、精噁唑禾草灵、fentrazamide、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、florasulam、精吡氟禾草灵、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、唑嘧磺草胺、氟草隆、氟咯草酮、乙羧氟草醚、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酯、氟丁酮、氟草烟、调嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamid、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、吡氟氯禾灵(-P-甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、唑吡嘧磺隆、iodosulfuron、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻草胺、苯嗪草酮、吡草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、pelargonic acid、二甲戊灵、pendralin、pentoxazone、甜草宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、噁草酸、异丙草胺、炔苯酰草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭草醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcitrione、甲磺草胺、甲嘧黄隆、sulfosate、sulfosulfuron、牧草胺、丁噻隆、特丁津、特丁净、噻吩草胺、thiafluamide、噻唑烟酸、thidiazimin、噻吩黄隆、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆、绿草定、灭草环、氟乐灵和氟胺黄隆。
此外,本发明活性化合物可以以其商业上可得的制剂和以由这些制剂制备的使用形式作为与增效剂的混合物存在。增效剂是可以增加活性化合物活性,而所添加的增效剂本身无需有活性的化合物。
由商业上可行的制剂制备的使用形式中的活性化合物的含量可以在较宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选在按重量计0.0001至1%间。
施用是以适合于使用形式的常规方式进行的。
此外,本发明活性化合物适合防治动物害虫,优选节肢动物和线虫类,特别是昆虫和属于蜘蛛类的节肢动物,这些害虫出现在农业、森林、贮藏产品和材料保护以及卫生领域。本发明活性化合物对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足目,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidiumvulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,例如,洁幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,具棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattella germanica)、家蟋蟀(Acheta domesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locusta migratoriamigratorioids)、殊种蚱蜢(Melanoplus differentialis)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,Phylloxera vastatrix、Pemphigus spp.、体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalinea spp.)。
缨翅目,例如,Frankliniella occidentalis、温室条蓟马(Hercinothrips femoralis)、Thrips palmi和棉蓟马(Thripstabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercusintermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimexlectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatomaspp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvata lugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotushederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupalus piniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeutapadella)、小菜蛾(Plutella maculipennis)、Plutella xylostella天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctischrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrixthurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Earias insulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Laphygma exigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolis flammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodoptera spp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsa pomonella)、粉蝶属(Pieris spp.)、禾草螟属(chilospp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestiakuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineolabisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoeciapodana)、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)、Cnaphalocerus spp.和Aulema oryzae。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizoperthadominica)、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsa decemlineata)、辣根猿叶甲(Phaedoncochleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachnavarivestis)、隐翅甲属(Atomaria spp.)、锯谷盗(Oryzaephilussurinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilusspp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopolites sordidus)、甘蓝荚象甲(Ceuthorrhynchusassimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestesspp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptushololeucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Triboliumspp.)、黄粉虫(Tenebrio molitor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)、褐新西兰肋翅鳃角金龟(Costelytra zealandica)和Lissorhoptusoryzophilus。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophila melanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophoraerythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyiaspp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、Liriomyza spp.、螫蝇属(Stomoxysspp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibiohortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbiaspp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitiscapitata)、油榄实蝇(Dacus oleae)、沼泽大蚊(Tipulapaludosa)、Tipula paludosa和Liviomyza spp.。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)、毛列蚤属(Ceratophyllus spp.)。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argasspp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssusgallinae)、茶藨瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptrutaoleivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalusspp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptes spp.)、皮螨属(Chorioptesspp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)、叶螨属(Tetranychus spp.)、Hemitarsonemus spp.和Brevipulpusspp.。
植物寄生性线虫包括短体线虫(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、起绒草茎线虫(Ditylenchus dipsaci)、半穿刺线虫(Tylenchulus semi penetrans)、异皮线虫(Heteroderaspp.)、Globodera spp.、根结线虫(Meloidogyne spp.)、滑刃线虫(Aphelenchoides spp.)、长针线虫(Longidorus spp.)、剑线虫(Xiphinema spp.)、毛刺线虫(Trichodorus spp.)和Bursaphelenchusspp.。
当将本发明的活性化合物通过叶部和土壤施用后,它们具有很高的杀虫和杀螨活性。
在一定的浓度或施用率时,本发明化合物还具有杀真菌作用。此外,它们也可以用作杀微生物剂和抗霉菌剂。
当用来防治卫生害虫和贮藏产品的害虫时,活性化合物对木材和陶土具有显著残留作用和对石灰处理过的底物上的碱具有良好的稳定性。
本发明活性化合物不仅对植物、卫生和贮藏产品害虫有活性,而且在兽医方面,对动物寄生虫(体外寄生虫)如硬蜱、隐喙蜱科、疥螨、恙螨、(叮咬和吸吮)蝇、寄生蝇幼虫、毛虱、鸟虱和蚤有活性。这些寄生虫包括:
虱目,例如,血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、虱属(Pediculus spp.)、阴虱属(Phthirus spp.)、盲虱属(Solenoptes spp.)。
食毛目及Amblycerina和细角亚目(Ischnocerina),例如,毛鸟虱属(Trimenopon spp.)、短角鸟虱属(Menopon spp.)、豆虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、畜虱属(Damalinea spp.)、啮毛虱属(Trichodectes spp.)和猫虱属(Felicola spp.)。
双翅目及长角亚目和短角亚目,例如,伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simuliumspp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomus spp.)、卢蚊属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotusspp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、Braula spp.、蝇属(Musca spp.)、齿股蝇(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、血蝇属(Haematobiaspp.)、Morellia spp.、厕蝇属(Fannia spp.)、舌蝇属(Glossinaspp.)、丽蝇属(Calliphora spp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、肉蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hippobosca spp.)、蜱蝇属(lipoptena spp.)和羊虱蝇属(Melophagus spp.)。
蚤目,例如,蚤属(Pulex spp.)、栉头蚤属(Ctenocephalidesspp.)、鼠客蚤属(Xenopsylla spp.)和毛列蚤属(Ceratophyllusspp.)。
半翅目,例如,臭虫属(Cimex spp.)、锥蝽属(Triatoma spp.)、红腹猎蝽属(Rhodnius spp.)和全圆蝽属(Panstrongylus spp.)。
蜚蠊目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattela germanica)和棕带蠊属(Suppella spp.)。
螨亚纲及后气亚目(Metastigmata)和中气亚目(Mesostigmata),例如,隐喙蜱属(Argas spp.)、钝喙蜱属(Ornithodorus spp.)、残喙蜱属(Otabius spp.)、硬蜱属(Ixodes spp.)、花蜱属(Amblyommaspp.)、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemaphysalis spp.)、眼玻蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)、刺皮螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸口螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
Actinedida(前气孔亚目)和粉螨目(无气孔亚目),例如,蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形属(Demodex spp.)、恙螨属(Trombiculaspp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophaus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、瘙螨属(Psoroptes spp.)、痒螨属(Chorioptes spp.)、耳癞螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedresspp.)、疙螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)和皮膜螨属(Laminosioptes spp.)。
本发明式(I)活性化合物也适合防治侵害如下动物的节肢动物:牲畜例如牛、绵羊、山羊、马、猪、猴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅、蜜蜂,其它家养动物,如狗、猫、笼养鸟、水箱中的鱼,和所谓的实验动物,例如仓鼠、豚鼠、大鼠和小鼠。通过防治这些节肢动物,旨在使死亡和产量(如肉、奶、毛、皮、蛋、蜜等)降低的情况减少。这样,通过使用本发明活性化合物,使更经济简单的动物饲养成为可能。
本发明活性化合物可以使用在兽医方面,使用是以已知的方式,通过外部施用,例如以片剂、胶囊、药水、兽用顿服剂、颗粒剂、膏剂、大丸剂、食入法、栓剂的方式,通过非肠道施药,例如注射(肌内、皮下、静脉内、腹腔内等)、植入,经鼻施用,经皮施用,例如通过沐浴或浸蘸、喷雾、浇泼、点涂、洗刷、喷粉的方式,以及借助含有活性化合物的成形物件,如颈环、耳标、尾牌、腿箍、笼头、标记设备等。
当给药于畜禽、家养动物等时,式(I)的活性化合物可以以制剂的形式(例如粉剂、乳剂、悬浮剂)的使用,所述的制剂中含有按重量计1至80%的活性化合物,该制剂可以直接施用或稀释100至10000倍后施用,或者它们可以以化学浴的形式使用。
此外,现已发现,本发明式(I)化合物对破坏工业材料的昆虫具有强的杀虫作用。
可以列举且是优选的昆虫是下列,但不限于这些昆虫:
甲虫如
北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophoruspilosis)、具斑窃蠹(Anobium punctatum)、报死窃蠹(Xestobiumrufovillosum)、梳角细脉窃蠹(Ptilinus pecticornis)、Dendrobiumpertinex、松窃蠹(Ernobium mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、桴粉蠹(Lyctus linesris)、柔毛粉蠹(Lyctus pubescens)、Trogoxylon aequale、鳞毛粉蠹(Minthesrugicollis)、材小蠹(Xyleborus spec.)、Tryptodendron spec.、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostyrchus capucins)、暗褐长蠹(Heterobostrychus brunneus)、长蠹属(Sinoxylon spec.)和竹长蠹(Dinoderus minutus)。
革翅目,如
小钢青树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、U.gigas taignus、U.augur。
白蚁,如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermesbrevis)、灰点异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、Reticulitermes santonecsis、避光散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermesdarwiniensis)、湿木白蚁(Zootermopsis nevadensis)和家白蚁(Coptotermes formosanus)。
衣鱼
如西洋衣鱼(Lepisma saccharina)。
在本文中,工业材料应理解为无生命的材料如优选的是塑料、胶粘剂、粘性材料、纸和板、皮革、木材和木制品以及漆。
木材和木制品是非常特别优选的受保护而使之不被昆虫侵害的材料。
可以用本发明的药剂或含有之的组合物保护的木材和衍生的木制品应理解为有下列含义,例如,建筑木料、木梁、铁道枕木、桥梁组件、船用跳板、木制车辆、板箱、模板、包装箱、电线杆、木质矿道顶木、木制的门窗、胶合板、碎料板、木工的制品、或通常用在建筑或细木工中的木制品。
本发明活性化合物可以以其原样、以其浓缩物或通常的常规制剂使用。所述的常规制剂是例如粉剂、颗粒剂、溶液、悬浮剂、乳剂或膏剂。
上述制剂可以以本身已知的方式制备,例如通过将活性化合物与至少一种溶剂或稀释剂、乳化剂、分散剂和/或粘合剂或固定剂、防水剂、(如果需要)干燥剂和UV稳定剂和(如果需要)着色剂和染料和其它加工辅助剂混合。
用于保护木材和木制品的杀虫组合物或浓缩物包含浓度为按重量计0.0001至95%,特别是按重量计0.001至60%的活性化合物。
所采用的组合物或浓缩物的量取决于昆虫的种类和密度,以及介质。所用最佳量可以在每种情况下由一系列试验来确定。然而,一般而言,以所要保护的材料为基准,采用按重量计0.0001至20%,优选按重量计0.001至10%的活性化合物已足已。
所用的溶剂和/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样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/或水和任选地乳化剂和/或润湿剂。
优选采用的有机化学溶剂是油性或油样溶剂,所述的溶剂具有大于35的挥发度和高于30℃的闪点,优选高于45℃。用作这种油性或油样溶剂的物质是低挥发性的,且不溶于水,这类物质适合的有矿物油或其芳族馏份或是含有矿物油的溶剂混合物,优选是石油溶剂、石油和/或烷基苯。
沸程为170到220℃的矿物油、沸程为170到220℃的石油溶剂、沸程为250到350℃的碇子油、沸程为160到280℃的石油或芳族化合物、松节油等是有利使用的。
在一个优选的实施方案中,所用的物质是沸程为180至210℃的液体脂族烃或沸程为180至220℃的脂族和芳族烃的高沸点混合物和/或碇子油和/或单氯萘,优选α-单氯萘。
挥发度高于35且闪点高于30℃、优选高于45℃的低挥发性有机油性或油样溶剂,可以部分地由低或中挥发性的有机化学溶剂置换,其前提条件是,溶剂混合物也具有高于35的挥发度且闪点高于30℃,优选高于45℃,且杀虫剂/杀真菌剂混合物在此溶剂混合物中是可溶的或可乳化的。
在一个优选的实施方案中,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置换。优选采用的物质是含有羟基和/或酯和/或醚基团的极性脂族有机化学溶剂,如例如乙二醇醚、酯类等。
在本发明范围内使用的有机化学粘合剂是本身已知的粘合干性油和/或合成树脂,它们可以用水稀释和/或在所采用的有机化学溶剂中是可溶的、可分散的或可乳化的,特别是那些由如下组成,或包含如下成分的粘合剂:丙烯酸树酯、乙烯树脂,例如聚乙酸乙烯酯、聚酯树脂、缩聚或加聚树脂、聚氨酯树脂、醇酸树脂或改性的醇酸树脂、酚树脂、烃类树脂如茚-香豆酮树脂、硅氧烷树脂、干性植物油和/或干性油和/或以天然和/或合成树脂为基础的物理干性粘合剂。
用作粘合剂使用的合成树脂可以以乳液、分散液或溶液的形式使用。沥青或沥青状物质也可以用作粘合剂,其量至多为按重量计10%。此外,可以采用特别是着色剂、染料、防水剂、遮味剂和抑制剂或抗腐蚀剂等。
根据本发明,组合物或浓缩物优选含有至少一种醇酸树脂或改性醇酸树脂和/或干性植物油作为粘合剂。根据本发明所优选采用的物质是油含量超过按重量计45%,优选50至68%的醇酸树脂。
所有的或部分上述粘合剂可以由固定剂(混合物)或增塑剂(混合物)置换。这些添加剂是旨在防止活性化合物以及挥发和结晶或沉淀。它们优选置换0.01至30%的粘合剂(以所用的粘合剂的100%为基准)。
增塑剂来自属于下列化学类的物质:邻苯二甲酸酯类,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,己二酸酯类,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,油酸酯类,如油酸丁酯,甘油醚类或高分子量乙二醇醚类、甘油酯类和对甲苯磺酸酯类。
固定剂化学上基于聚乙烯基烷基醚类如聚乙烯基甲基醚,或酮类如二苯甲酮或亚乙基二苯甲酮。
特别适合的溶剂或稀释剂也可以是水,任选地是水与一或多种上述有机化学溶剂或稀释剂、乳化剂和分散剂的混合物。
特别有效的木材保护通过工业规模的浸渍工艺,例如真空、双真空或压力工艺的方式获得。
直接可用的组合物还可以任选地包含其它杀虫剂和任选地包含一或多种杀真菌剂。
可能混合于其中的另外的适合组分优选是WO94/29268中提到的杀虫剂和杀真菌剂。在该文献中提到的化合物明确地说是本发明申请的一部分。
可以非常特别优选地混合于其中的组分是杀虫剂如毒死蜱、辛硫磷、氟硅菊酯、氟氯氰菊酯、甲体氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、啶虫脒、氟虫脲、氟铃脲和杀虫隆,以及杀真菌剂如氟环唑、己唑醇、戊环醇、丙环唑、戊唑醇、环唑醇、叶菌唑、抑霉唑、苯氟磺胺、甲苯氟磺胺、3-碘代-2-丙炔基丁基氨基甲酸酯、N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
本发明的活性化合物可以特别有效地用于防治损害植物的昆虫例如辣根猿叶甲(Phaedon cochleariae)幼虫、黑尾叶蝉(Nephotettixcincticeps)幼虫和桃蚜(Myzus persicae)幼虫。
除了所述的杀螨、除草和杀虫性质外,本发明活性化合物的杀真菌活性也是显明的。在“体内”和“体外”研究中,可以观察到广的杀真菌效果。
此外,注意到,所述的活性化合物还特别适用于防治受感染植物上的霉(mildew)、叶斑(1eaf blotch)和镰刀菌(Fusaria)。
本发明活性化合物的制备和应用通过下列实施例说明。
制备实施例
实施例1第I-1-a-1号化合物
(方法A)
将1.2g 2-乙氧基吡咯啉和1g 4-氯苯甲酰基乙腈在20ml甲苯中的混合物在100℃搅拌1小时。与甲苯一起共沸蒸馏掉产生的乙醇。冷却到20℃后,通过加入己烷使反应混合物结晶,并吸滤出晶体。
得到1.1g(理论量的74%)的3-(4-氯苯基)-3-氧代-2-吡咯烷-2-亚基丙腈,熔点为156-158℃。
实施例2第I-1-a-54号化合物
(方法E)
将在20℃制备的1.85g 3-氧代-3-(4-溴苯基)-2-哌啶-2-亚基丙腈在20ml二甲氧基乙烷中的溶液在氩气保护下与1g 4-氯苯基硼酸和360mg四(三苯基膦)钯混合,并将混合物在20℃搅拌15分钟。然后加入10ml 20%的碳酸钠溶液,并将混合物在80℃加热24小时。然后用浓盐酸酸化混合物,用水稀释,与乙酸乙酯一起振摇,分出有机相,用水洗涤,干燥并过滤。从滤液中蒸掉溶剂。
得到1.9g(理论量的96%)的3-(4’-氯联苯-4-基)-3-氧代-2-哌啶-2-亚基丙腈,熔点为134℃。
实施例3第I-1-b-1号化合物
(方法D)
在0℃,将1g根据实施例1制备的3-(4-氯苯基)-3-氧代-2-吡咯烷-2-亚基丙腈溶解在10ml的THF中,与0.16g的NaH(60%纯)混合,然后将混合物在20℃加热4小时。然后加入0.65g的2-氯-5-氯甲基吡啶并将混合物煮沸回流4小时,再加入100mg二氮杂二环辛烷(DABCO),然后再将混合物加热回流24小时。然后将混合物倒入冰水中,吸滤出固体残留物,液相与乙酸乙酯一起振摇,分出有机相,用水洗涤,过滤。通过在硅胶上用己烷/丙酮7∶3作为流动相进行柱层析来分离溶液中所含的化合物。
蒸发溶剂后,主要洗脱部分之一给出了0.65g(理论量的44%)的3-(4-氯苯基)-2-[1-(6-氯吡啶-3-基甲基)吡咯烷-2-亚基]-3-氧代丙腈,熔点为142-144℃。
(方法D)
在0℃,将1.5g的3-(2-氯苯基)-3-氧代-2-吡咯烷-2-亚基丙腈溶解在10ml的THF中,与0.5g的NaH(60%纯)混合,然后将混合物在20℃加热4小时。加入在10ml的THF中的1.1g的2-氯-5-氯甲基噻唑和100mg二氮杂二环辛烷(DABCO)。将混合物小心地保持在室温(20℃)下,通过薄层层析监测反应进程。然后将混合物倒入冰水中,吸滤出固体残留物,液相与乙酸乙酯一起振摇,分出有机相,用水洗涤,过滤。通过在硅胶上用正己烷/丙酮7∶3作为流动相进行柱层析来分离溶液中所含的化合物。
蒸发溶剂后,主要洗脱部分之一给出了0.4g(理论量的13%)的3-(2-氯苯基)-2-[3-(2-氯噻唑-5-基)-1-(2-氯噻唑-5-基甲基)吡咯烷-2-亚基]-3-氧代丙腈。
实施例5第I-1-c-1号化合物
(方法D)
在0℃,将1g根据实施例1制备的3-(4-氯苯基)-3-氧代-2-吡咯烷-2-亚基丙腈溶解在10ml的THF中,与0.3g的NaH(60%纯)混合,然后将混合物加热到20℃保持2小时。加入在10ml的THF中的0.8g的氯代苯甲酰氯,然后将混合物在室温下再搅拌24小时。将反应混合物倒入冰水中,用乙酸乙酯萃取,萃取液用硫酸镁干燥,减压蒸发溶剂。残留物在硅胶上用正己烷/丙酮7∶3作为流动相进行柱层析。蒸发溶剂后,主要洗脱部分之一给出了0.2g(理论量的14%)的2-[1-(4-氯苯甲酰基)吡咯烷-2-亚基]-3-(4-氯苯基)-3-氧代丙腈,熔点为218℃。
实施例6第I-1-d-1号化合物
(方法A)
将0.9g 6-(4-溴苯基)-2-乙氧基四氢吡啶和0.5g氯代苯甲酰基乙腈在10ml甲苯中的混合物加热到120℃,并保持在该温度下2小时。通过在硅胶上用二氯甲烷/乙酸乙酯5∶3作为流动相进行柱层析来分离溶液中所含的反应产物。
蒸发溶剂后,主要洗脱部分给出了0.9g(理论量的77.6%)的2-[6-(4-溴苯基)哌啶-2-亚基]-3-(4-氯苯基)-3-氧代丙腈。
(根据式(III)的方法A的中间体;化合物III-1)
将在200ml二氯甲烷中的63g的DL-焦谷氨酸乙酯在10分钟内滴加到500ml四氟硼酸三乙基氧鎓的溶液(Meerwein盐,在二氯甲烷中的1M溶液),将混合物加热回流24小时。然后将溶液冷却到0℃,小心地与在300ml水中的63g碳酸钠混合。用二氯甲烷萃取反应产物,干燥有机相,过滤,随后在水泵真空下汽提掉溶剂。
(方法A)
将6.1g所制备的5-乙氧基-3,4-二氢-2H-吡咯-2-羧酸乙酯和6g氯苯甲酰基乙腈在50ml甲苯中的混合物在100℃搅拌1小时。与甲苯一起共沸蒸馏掉产生的乙醇。冷却到20℃后,通过加入己烷使反应混合物结晶,并吸滤出晶体。通过在硅胶上用正己烷/丙酮7∶3作为流动相进行柱层析来分离主产物。
蒸发溶剂后,主要洗脱部分给出了6.9g(理论量的67%)的5-[2-(4-氯苯基)-1-氰基-2-氧代亚乙基]吡咯烷-2-羧酸乙酯。熔点为108-110℃。
实施例8第I-1-d-3号化合物
将4.8g根据实施例7所制备的5-[2-(4-氯苯基)-1-氰基-2-氧代亚乙基]吡咯烷-2-羧酸乙酯在40℃溶解在30ml乙醇中,与10ml 20%的氢氧化钠混合。将混合物在所述温度下搅拌1小时,然后在水泵真空下浓缩,用HCl调节pH至1-2。
作为残留物得到了2.5g的5-[2-(4-氯苯基)-1-氰基-2-氧代亚乙基]吡咯烷-2-羧酸,熔点为134-136℃。
(根据式(V)的式(III)化合物的中间体;化合物V-1)
将38.5g的6-(4-溴苯基)哌啶-2-酮和31g的[2,4-二(4-甲氧基苯基)-1,3,2,4-二硫杂二磷烷-2,4-二硫化物](Lawesson’s试剂)在200ml无水甲苯中加热回流大约2小时。通过薄层层析监测反应进程。通过在硅胶上用二氯甲烷/乙酸乙酯5∶3作为流动相进行柱层析来分离溶液中所含的反应产物。
(根据式(III)的方法A的中间体)
在20℃,将8g的6-(4-溴苯基)哌啶-2-硫酮溶解在150ml丙酮中并依次与10g碳酸钾和10g碘甲烷混合。在24小时时间内,用薄层层析监测反应进程,在此期间将混合物加热回流。冷却后,吸滤出固体,浓缩滤液。通过在硅胶上用二氯甲烷/乙酸乙酯5∶3作为流动相进行柱层析来分离溶液中所含的反应产物。
蒸发溶剂后,主要洗脱部分给出了2.1g(理论量的25%)的黄色油状的6-(4-溴苯基)-2-甲硫基-2,3,4,5-四氢吡啶。
(根据式(II)的方法A的中间体;化合物II-1)
先将80g的4-溴苯甲酸乙酯加到2000ml二噁烷和50g乙腈中。加入三滴三[2-(2-甲氧基乙氧基)乙基]胺(TDA-1)后,将混合物加热到90℃。随后,一次一点点地加入70g叔丁醇钾,并将混合物加热回流3小时。然后在水泵真空下浓缩混合物,残留物吸收到水中,用10%HCl酸化,与二氯甲烷混合,过滤,二氯甲烷相用饱和碳酸氢钠溶液萃取,将干燥后的有机相浓缩至干。
作为残留物得到82g(理论量的72%)的3-(4-溴苯基)-3-氧代丙腈。
在保护气体(氩气)下,先将5.84g的NaH(60%纯)加入到147ml甲苯中。在20℃,滴加在9ml甲苯中的10.51g的氰基乙酸叔丁酯(98%纯),将混合物在室温下搅拌45分钟。然后滴加在9ml甲苯中的18.5g的3-硝基-5-三氟甲基苯甲酰氯,将混合物再搅拌24小时。然后小心地加入168ml水,分离甲苯相,用约190ml水洗涤,合并的水相用二氯甲烷洗涤两次,用2N HCl酸化,然后用二氯甲烷萃取两次。合并的有机相用水洗涤,用硫酸钠干燥,水泵真空下浓缩。
(根据式(II)的方法A的中间体;化合物II-2)
先将13g的2-氰基-3-(3-硝基-5-三氟甲基苯基)-3-氧代丙酸叔丁酯加到55ml甲苯中,并在20℃,与0.07g的对甲苯磺酸(一水合物)混合。将混合物加热回流2小时,并用薄层层析监测反应进程。随后,浓缩溶液,残留物吸收到二氯甲烷/甲醇(99∶1)中,通过硅胶过滤,汽提掉溶剂。
得到了5.5g(理论量的59%)的3-(3-硝基-5-三氟甲基苯基)-3-氧代丙腈。
(方法C)
将3.06g(20mmol)氯化1-甲基-2-氯-2-吡咯啉亚铵悬浮在10ml甲苯中。在保护气体下,在0℃下,先后滴加1.79g(19mmo1)的4-氯苯甲酰基乙腈(为在30ml氯仿中的溶液)和3.06ml(22mmol)的三乙胺(为在30ml氯仿中的溶液)。加入过程是在有效地冷却下进行的。在0℃搅拌1小时和在室温下搅拌2小时后,在0℃下再加入3.06g的氯化1-甲基-2-氯-2-吡咯啉亚铵和4.18ml的三乙胺。将混合物在室温下搅拌48小时。随后将反应混合物倒入30ml冰水中,用各50ml氯仿萃取三次。氯仿相用硫酸镁干燥,然后浓缩至干。
通过在硅胶上用己烷/乙酸乙酯1∶1作为流动相进行柱层析来分离反应产物。
蒸发溶剂后,主要洗脱部分给出了620mg(理论量的24%)的3-(4-氯苯基)-3-氧代-2-(1-甲基吡咯烷-2-亚基)丙腈,熔点115℃。
实施例13第I-1-a-151号化合物
(方法K)
将1g的实施例I-1-a-55的化合物溶解在10ml甲苯中。将混合物与1.58g(3.9mmol)的Lawesson’s试剂混合并加热至回流。1小时后,通过用己烷/乙酸乙酯作为移动相进行薄层层析来检测,不再能够检测到原料。汽提掉一半溶剂,吸滤出沉淀的结晶。通过在硅胶上用己烷/乙酸乙酯作为流动相进行柱层析来分离进一步浓缩后沉淀出的产物。
蒸发溶剂后,主要洗脱部分给出了0.560mg(理论量的53%)的3-(4-氯苯基)-3-硫代-2-哌啶-2-亚基丙腈,熔点1 37℃。
实施例14第I-1-a-150号化合物
将257g(1.02mmol)的实施例I-1-a-62的化合物与246mg(1.2mmol)的叠氮化三甲基锡一起在甲苯中加热回流24小时。24小时后,加入另外120mg的叠氮化锡,再将混合物加热回流5小时。随后吸滤出锡加合物。加入5ml 2N的氢氧化钠溶液后,原料分离出来,吸滤之。用2N的盐酸将pH值调节到1,将反应混合物冷却到0℃,从混合物中吸滤出所制得的产物。
得到了0.06g(理论量的18%)的固体状的3-(4-四唑基苯基)-3-氧代-2-哌啶-2-亚基丙腈,熔点大于220℃。
实施例15第I-1-a-137号化合物
将2.33g(8.6mmol)的实施例I-1-a-63的化合物溶解在100ml乙醇(p.a.)中,向溶液中加入300mg Raney镍。使氮气通过反应混合物5分钟,接着再通入大气压下的氢气8小时。再用氮气冲洗混合物5分钟。滤掉Raney镍,用20ml乙醇和50ml二氯甲烷漂洗。合并滤液,蒸发至干,残留物在高真空下干燥。
得到了2.03g(理论量的97.8%)的固体状的3-(4-硝基苯基)-3-氧代-2-哌啶-2-亚基丙腈,熔点182℃。
在保护气体下,先将在5ml二氯甲烷中的0.4g(1.66mmol)的实施例I-1-a-137的化合物加到已加热除湿过的设备中,将混合物冷却到-20℃。在该温度下,加入0.28ml(2.0mmol)的三乙胺,然后再滴加0.33ml(1.98mmol)的三氟甲磺酸酐。将混合物在-20℃下搅拌15分钟。温热至0℃,再搅拌2小时。为了使反应完全,在-20℃下再加入0.33mmol的三氟甲磺酸酐。温热至0℃,再搅拌混合物1小时。
将反应混合物用50ml的二氯甲烷稀释,倒入20ml 0℃的1N HCl中。分离有机相,用硫酸镁干燥,用旋转蒸发器浓缩。通过在硅胶上用乙酸乙酯/环己烷1∶1作为流动相进行柱层析分离反应产物。
得到了316mg(理论量的51%)的3-[4-(三氟甲磺酰基氨基)苯基]-3-氧代-2-哌啶-2-亚基丙腈,熔点197℃。
将1.5g(5.73mmol)的实施例I-2-a-2的化合物、0.91g(8.6mmol)的硫代乙醇酸甲酯和0.91g碳酸钠在10ml无水丙酮中加热到80℃。2小时后,加入另外的8.6mmol的硫代乙醇酸甲酯和8.6mmol甲醇钠,并将混合物加热回流24小时。冷却到室温后,将反应混合物倒入150ml的1M HCl中。将反应产物作为固体残留物滤出,用10ml甲基叔丁基醚反复洗涤。
得到了1.350g的3-[(2-甲氧基羰基甲硫基)吡啶-5-基]-3-氧代-2-哌啶]-2-亚基丙腈(理论量的71%),熔点146℃。
实施例18第I-2-a-7号化合物
在0℃,先将700mg(2.1mmol)的实施例I-2-a-6的化合物加入到1.1ml的2N氢氧化钠和甲醇的1∶1混合物中。随后在0℃下将混合物搅拌1小时,并在室温下将混合物搅拌4小时。用6N的盐酸将反应液的pH值调节到6。通过在粘土上挤压和在高真空下干燥除去沉淀的产物中的湿气。
得到了551mg(理论量的82.7%)的3-[4-(巯基乙酸)吡啶基]-3-氧代-2-吡啶-2-亚基丙腈,熔点155℃。
类似于制备实施例1和2,并按照制备式(I-1-a)化合物的一般描述,得到了下列化合物:
表1
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-2 | O | 4-OCH3 | - | H | 1 | 145 |
I-1-a-3 | O | 3,5-Cl2 | - | H | 1 | 124 |
I-1-a-4 | O | 4-t-C4H9 | - | H | 1 | 204-205 |
I-1-a-5 | O | 4-CH3 | - | H | 1 | 166-168 |
I-1-a-6 | O | 2,6-Cl2 | - | H | 1 | 196-198 |
I-1-a-7 | O | 2,4-Cl2 | - | H | 1 | 120 |
I-1-a-8 | O | 3,4-Cl2 | - | H | 1 | 179-180 |
I-1-a-9 | O | 2,5-Cl2 | - | H | 1 | 152 |
I-1-a-10 | O | 4-O-C6H5 | - | H | 1 | 136-138 |
表1(续)
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-11 | O | 4-CF3 | - | H | 1 | 138-140 |
I-1-a-12 | O | 4-OCF3 | - | H | 1 | 98 |
I-1-a-13 | O | 4-Br | - | H | 1 | 192 |
I-1-a-14 | O | 3,5-(CF3)2 | - | H | 1 | 78 |
I-1-a-15 | O | 3-O-C6H5 | - | H | 1 | 178 |
I-1-a-16 | O | 2-NO2 | - | H | 1 | 206 |
I-1-a-17 | O | 3-NO2 | - | H | 1 | 223 |
I-1-a-18 | O | 3-Cl,4-F | - | H | 1 | 176 |
I-1-a-19 | O | 4-Cl,3-F | - | H | 1 | 178 |
I-1-a-20 | O | 4-CN | - | H | 1 | 215 |
I-1-a-21 | O | 4-NO2 | - | H | 1 | 221 |
I-1-a-22 | O | 3-Br | - | H | 1 | 193 |
I-1-a-23 | O | 2-S-CHF2 | - | H | 1 | 206 |
I-1-a-24 | O | 2,4-Cl2,5-F | - | H | 1 | 175 |
I-1-a-25 | O | 3-CF3 | - | H | 1 | 119 |
I-1-a-26 | O | 3-Cl | - | H | 1 | 178 |
I-1-a-27 | O | 3,5-Cl2,4-F | - | H | 1 | 203 |
I-1-a-28 | O | 4-Cl,2-F | - | H | 1 | 182 |
I-1-a-29 | O | 3-CF3,5-CH3 | - | H | 1 | 143 |
I-1-a-30 | O | 3-Cl,4,5-F2 | - | H | 1 | 160 |
I-1-a-31 | O | 2-F | - | H | 1 | 168 |
I-1-a-32 | O | 3-F | - | H | 1 | 167 |
I-1-a-33 | O | 4-Cl,3-CF3 | - | H | 1 | 156 |
I-1-a-34 | O | 4-CN,2,5-F2 | - | H | 1 | 206 |
I-1-a-35 | O | 2,3-F2 | - | H | 1 | 185 |
I-1-a-36 | O | 4-CF3,3-F | - | H | 1 | 185 |
I-1-a-37 | O | 3,4-O-CF2-O- | - | H | 1 | 159 |
表1(续)
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-38 | O | 3,5-(CH3)2 | - | H | 1 | 165 |
I-1-a-39 | O | 3,4,5-(OCH3)3 | - | H | 1 | 159 |
I-1-a-40 | O | 2-Br,4-OCH3 | - | H | 1 | 216 |
I-1-a-41 | O | 4-(4′-Cl-C6H4)- | - | H | 1 | 131 |
I-1-a-42 | O | 2,4-Cl2 | - | H | 2 | 100 |
I-1-a-43 | O | 4-t-C4H9 | - | H | 2 | 169-170 |
I-1-a-44 | O | 4-CH3 | - | H | 2 | 165 |
I-1-a-45 | O | 3,4-Cl2 | - | H | 2 | 135 |
I-1-a-46 | O | 2,5-Cl2 | - | H | 2 | 102 |
I-1-a-47 | O | 4-OCH3 | - | H | 2 | 104 |
I-1-a-48 | O | 3,5-Cl2 | - | H | 2 | 90-92 |
I-1-a-49 | O | 2,6-Cl2 | - | H | 2 | 176-178 |
I-1-a-50 | O | 4-O-C6H5 | - | H | 2 | 128-130 |
I-1-a-51 | O | 4-CF3 | - | H | 2 | 126-128 |
I-1-a-52 | O | 4-OCF3 | - | H | 2 | 82-84 |
I-1-a-53 | O | 4-Br | - | H | 2 | 149 |
I-1-a-54 | O | 4-(4′-Cl-C6H4)- | - | H | 2 | 134 |
I-1-a-55 | O | 4-Cl | - | H | 2 | 149 |
I-1-a-56 | O | 3,5-(CF3)2 | - | H | 2 | 64 |
I-1-a-57 | O | 2-NO2 | - | H | 2 | 222 |
I-1-a-58 | O | 3-O-C6H5 | - | H | 2 | 油状物 |
I-1-a-59 | O | 3-NO2 | - | H | 2 | 194 |
I-1-a-60 | O | 3-Cl,4-F | - | H | 2 | 148 |
I-1-a-61 | O | 4-Cl,3-F | - | H | 2 | 167 |
I-1-a-62 | O | 4-CN | - | H | 2 | 196 |
I-1-a-63 | O | 4-NO2 | - | H | 2 | 217 |
I-1-a-64 | O | 3-Br | - | H | 2 | 107 |
I-1-a-65 | O | 2-S-CHF2 | - | H | 2 | 130 |
表1(续)
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-66 | O | 2,4-Cl2,5-F | - | H | 2 | 132 |
I-1-a-67 | O | 3-CF3 | - | H | 2 | 129 |
I-1-a-68 | O | 3-Cl | - | H | 2 | 123 |
I-1-a-69 | O | 3-C6H5 | - | H | 2 | 188 |
I-1-a-70 | O | 3-(3′-Cl,4′-F-C6H3)- | - | H | 2 | 216 |
I-1-a-71 | O | 3-(4′-F-C6H4)- | - | H | 2 | 234 |
I-1-a-72 | O | 3-(3′-NO2-C6H4)- | - | H | 2 | 157 |
I-1-a-73 | O | 3,5-Cl2,4-F | - | H | 2 | 150 |
I-1-a-74 | O | 4-Cl,2-F | - | H | 2 | 177 |
I-1-a-75 | O | 3-CF3,5-CH3 | - | H | 2 | 114 |
I-1-a-76 | O | 3-Cl,4,5-F2 | - | H | 2 | 140 |
I-1-a-77 | O | 2-F | - | H | 2 | 154 |
I-1-a-78 | O | 3-F | - | H | 2 | 145 |
I-1-a-79 | O | 4-Cl,3-CF3 | - | H | 2 | 141 |
I-1-a-80 | O | 4-CN,2,5-F2 | - | H | 2 | 187 |
I-1-a-81 | O | 2,3-F2 | - | H | 2 | 210 |
I-1-a-82 | O | 4-CF3,3-F | - | H | 2 | 160 |
I-1-a-83 | O | 3,4-O-CF2-O- | - | H | 2 | 163 |
I-1-a-84 | O | 3,5-Br2 | - | H | 2 | 118 |
I-1-a-85 | O | 3,5-(CH3)2 | - | H | 2 | 133 |
I-1-a-86 | O | 3,4,5-(OCH3)3 | - | H | 2 | 139 |
I-1-a-87 | O | 3,5-(OC2H5)2 | - | H | 2 | 105 |
I-1-a-88 | O | 3-Br,4-OCH3 | - | H | 2 | 171 |
I-1-a-89 | O | 4-Cl | - | H | 3 | 158 |
I-1-a-90 | O | 4-CH3 | - | H | 3 | 124 |
I-1-a-91 | O | 4-OCH3 | - | H | 3 | 82 |
I-1-a-92 | O | 3-Cl | - | H | 3 | 136 |
I-1-a-93 | O | 2,4-Cl2 | - | H | 3 | 167 |
表1(续)
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-94 | O | 3,5-(CF3)2 | - | H | 3 | 129 |
I-1-a-95 | O | 3-Br | - | H | 3 | 137 |
I-1-a-96 | O | 3-NO2 | - | H | 3 | 127 |
I-1-a-97 | O | 3-O-C6H5 | - | H | 3 | 103 |
I-1-a-98 | O | 3-CF3 | - | H | 3 | 145 |
I-1-a-99 | O | 4-Cl,3-F | - | H | 3 | 143 |
I-1-a-100 | O | 3-Cl,4-F | - | H | 3 | 145 |
I-1-a-101 | O | 3-Cl | - | H | 3 | 139 |
I-1-a-102 | O | 4-CN,2,5-F2 | - | H | 3 | 192 |
I-1-a-103 | O | 2,4,5-F3 | - | H | 1 | 174 |
I-1-a-104 | O | 3-NO2,5-CF3 | - | H | 1 | 152 |
I-1-a-105 | O | 4-Cl,2,5-F2 | - | H | 1 | 162 |
I-1-a-106 | O | 3,4,5-(OC2H5)3 | - | H | 1 | 166 |
I-1-a-107 | O | 2,4-F2 | - | H | 1 | 180 |
I-1-a-108 | O | 4-CO2CH3 | - | H | 1 | 207 |
I-1-a-109 | O | 4-CO2H | - | H | 1 | >220 |
I-1-a-110 | O | 4-Cl | - | CH3 | 1 | 115 |
I-1-a-111 | O | 2,5-F2,4-CN | - | CH3 | 1 | 158 |
I-1-a-112 | O | 2-F,4-Br | - | H | 1 | 195 |
I-1-a-113 | O | 2,6-Cl2,4-CF3 | - | H | 1 | 114 |
I-1-a-114 | O | 2-F,4-NO2 | - | H | 1 | 176 |
I-1-a-115 | O | 2-F,4-CF3 | - | H | 1 | 169 |
I-1-a-116 | O | 2-CF3 | - | H | 1 | 148 |
I-1-a-117 | O | 3,4-O-(CF2)2-O- | - | H | 1 | 109 |
I-1-a-118 | O | 2,3-O-CF2-O- | - | H | 1 | 147 |
I-1-a-119 | O | 2-Cl,4-SCH3 | - | H | 1 | 174 |
I-1-a-120 | O | 2,4-Cl2,5-NO2 | - | H | 1 | 190 |
I-1-a-121 | O | 2,6-F2 | - | H | 1 | 184 |
表1(续)
化合物号 | K | T | Yn | Z | m | M.p.℃ |
I-1-a-122 | O | 2-Cl,3-CF3 | - | H | 1 | 206 |
I-1-a-123 | O | 4-OCF3,3-NO2 | - | H | 1 | 113 |
I-1-a-124 | O | 2-NO2,4-Cl | - | H | 1 | 184 |
I-1-a-125 | O | 4-Cl | 3,3-(CH3)2 | H | 1 | 141 |
I-1-a-126 | O | 4-Cl | 5,6-CH=CH-CH=CH- | H | 2 | 196 |
I-1-a-127 | O | 2,5-F2,4-CN | 5,6-CH=CH-CH=CH- | H | 2 | 215 |
I-1-a-128 | O | 3,5-(CF3)2 | 5,6-CH=CH-CH=CH- | H | 2 | 167 |
I-1-a-129 | O | 2,4,5-F3 | - | H | 2 | 189 |
I-1-a-130 | O | 3-NO2,5-CF3 | - | H | 2 | 138 |
I-1-a-131 | O | 4-Cl,2,5-F2 | - | H | 2 | 186 |
I-1-a-132 | O | 3,4,5-(OC2H5)3 | - | H | 2 | 155 |
I-1-a-133 | O | 2,4-F2 | - | H | 2 | 168 |
I-1-a-134 | O | 4-CO2CH3 | - | H | 2 | 179 |
I-1-a-135 | O | 4-CO2H | - | H | 2 | >220 |
I-1-a-136 | O | 4-Br,2-F | - | H | 2 | 175 |
I-1-a-137 | O | 4-NH2 | - | H | 2 | 182 |
I-1-a-138 | O | 4-NHSO2CF3 | - | H | 2 | 197 |
I-1-a-139 | O | 2-CF3 | - | H | 2 | 153 |
I-1-a-140 | O | 2,6-Cl2,4-CF3 | - | H | 2 | 164 |
I-1-a-141 | O | 2-F,4-NO2 | - | H | 2 | 192 |
I-1-a-142 | O | 2-F,4-CF3 | - | H | 2 | 180 |
I-1-a-143 | O | 4-SCH3,2-Cl | - | H | 2 | 128 |
I-1-a-144 | O | 2,4-Cl2,5-NO2 | - | H | 2 | 204 |
I-1-a-145 | O | 4-Cl,2-F,5-NO2 | - | H | 2 | 177 |
I-1-a-146 | O | 4-OCF3,3-NO2 | - | H | 2 | 113 |
I-1-a-147 | O | 4-OCF3,3-NH2 | - | H | 2 | 141 |
类似于制备实施例1,并按照有关制备的一般描述,得到了下列式I-2-a的化合物:
表2
化合物号 | T | Yn | m | M.p.℃ |
I-2-a-1 | 2-Cl | - | 1 | 156-158 |
I-2-a-2 | 2-Cl | - | 2 | 258-260 |
I-2-a-3 | 2,6-Cl2,4-CH3 | - | 1 | >220 |
I-2-a-4 | 6-Cl | - | 1 | 30 |
I-2-a-5 | 2-Cl | 5,6-CH=CH-CH=CH- | 2 | 183 |
I-2-a-6 | 2-S-CH2-CO2-CH3 | - | 2 | 146 |
I-2-a-7 | 2-S-CH2-CO2-H | - | 2 | 155 |
I-2-a-8 | 2,6-Cl2 | - | 2 | 121 |
I-2-a-9 | 2,6-Cl2,4-CH3 | - | 2 | 176 |
I-2-a-10 | 2-S-4-[(4′-C6H5)-C6H4] | - | 2 | 197 |
I-2-a-11 | 6-Cl | - | 2 | 179 |
类似于制备实施例1,并按照有关制备的一般描述,得到了下列式I-3-a的化合物:
表3
化合物号 | T | m | M.p.℃ |
I-3-a-1 | 2-Br | 1 | 201 |
I-3-a-2 | 3-Br | 1 | 198 |
I-3-a-3 | 2-Cl | 2 | 141 |
I-3-a-4 | 2-Br | 2 | 159 |
I-3-a-5 | 3-Br | 2 | 215 |
I-3-a-6 | 3-Br | 3 | 162 |
I-3-a-7 | 2-Cl | 3 | 176 |
I-3-a-8 | 2-Br | 3 | 163 |
I-3-a-9 | 3-(4-Cl′-C6H4),2-CF3 | 1 | 176 |
I-3-a-10 | 2,3-(CH=CH-CCl=CH)- | 1 | 198 |
I-3-a-11 | 2-(4-Cl′-C6H4) | 2 | 207 |
I-3-a-12 | 3-(4-Cl′-C6H4),2-CF3 | 2 | 170 |
I-3-a-13 | 2-(3-Cl′,4-F′-C6H3) | 2 | 175 |
I-3-a-14 | 2-(3,5-(CF3)′2-C6H3) | 2 | >223 |
I-3-a-15 | 2-(4-F′-C6H4) | 2 | 195 |
I-3-a-16 | 2-(3-NO2′-C6H4) | 2 | 202 |
表4
化合物号 | K | T | Yn | m | M.p.℃ |
I-4-a-1 | O | 7-Cl | - | 1 | >220 |
I-4-a-2 | O | 7-Cl | - | 2 | >220 |
表5
化合物号 | K | T | Yn | m | M.p.℃ |
I-5-a-1 | O | 2-SCH3,5-Br | - | 1 | 170 |
I-5-a-2 | O | 2-SCH3,5-Br | - | 2 | 180 |
表6
化合物号 | K | T | Yn | m | M.p.℃ |
I-6-a-1 | O | H | - | 1 | 199 |
I-6-a-2 | O | H | - | 2 |
类似于制备实施例7,得到了下列式I-1-d-4的化合物,熔点222-224℃:第I-1-d-4号化合物类似于制备实施例3,得到了下列式I-1-d-5的化合物,熔点130-132℃:第I-1-d-5号化合物
实施例
辣根猿叶甲幼虫试验
溶剂: 7份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用水将此乳油稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片浸入所需浓度的活性化合物制备液,在叶片仍湿润时,移接辣根猿叶甲(Phaedon cochleariae)幼虫。
在所需的一段时间后,测定死亡百分率。100%指甲虫幼虫均被杀死;0%指没有甲虫幼虫被杀死。
在此试验中,例如,下列制备实施例的化合物显示出良好的活性:I-1-a-11、I-1-a-12、I-1-a-52。
实施例
斜纹夜蛾试验
溶剂: 7份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用水将此乳油稀释至所需浓度。
将甘蓝(Brassica oleracea)叶片浸入所需浓度的活性化合物制备液,在叶片仍湿润时,移接斜纹夜蛾(Spodoptera frugiperda)毛虫。
在所需的一段时间后,测定死亡百分率。100%指毛虫均被杀死;0%指没有毛虫被杀死。
在此试验中,例如,下列制备实施例的化合物显示出良好的活性:I-2-a-2、制备实施例3的化合物。
实施例
叶螨试验(抗0P/浸蘸处理)
溶剂: 7份重量二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,并用水将此乳油稀释至所需浓度。
将长满所有发育虫期二点叶螨(Tetranychus urticae)的菜豆(Phaseolus vulgaris)植株浸入所需浓度的活性化合物制备液。
在所需的一段时间后,测定死亡百分率。100%指叶螨均被杀死;0%指没有叶螨被杀死。
在此试验中,例如,下列制备实施例的化合物显示出良好的活性:I-1-a-7、I-1-a-48、I-1-a-56。
实施例
芽后试验
溶剂: 5份重量丙酮
乳化剂: 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。三周后,与未处理对照的发育相比较来评估对植物的百分损害程度。
数值的含义如下:
0%=无作用(与未处理相同)
100%=完全破坏
在此试验中,例如,制备实施例I-1-a-9、I-1-a-14、I-1-a-20、I-1-a-54、I-1-a-55、I-1-a-62、I-2-a-2的化合物对杂草显示出强活性,并且它们中的一些能被作物例如小麦很好地耐受。
实施例
芽前试验
溶剂: 5份重量丙酮
乳化剂:1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时,将1份重量的活性化合物与所述量的溶剂混合,将所述量的乳化剂加入,并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中,约24小时后,土壤用活性化合物制剂浇水,有利的是保持单位面积上的水量恒定。活性化合物在制剂中的浓度并不重要,重要的是每单位面积活性化合物的施用率。三周后,与未处理对照的发育相比较来评估对植物的百分损害程度。
数值的含义如下:
0%=无作用(与未处理相同)
在此试验中,例如,制备实施例I-1-a-14、I-1-a-46、I-1-a-51、I-1-a-52、I-1-a-53、I-1-a-54、I-1-a-55、I-1-a-62、I-1-a-66、I-2-a-2的化合物对杂草显示出强活性,并且它们中的一些能被作物例如小麦和大豆很好地耐受。
Claims (11)
K表示氧或硫,
Y表示卤素或各任选被取代的烷基、烷氧基、苯基、苯基烷基、杂芳基、杂芳基烷基或表示下式基团:—CO2R1或
或两个相邻的Yn表示各任选被取代的饱和或不饱和的环,该环可以任选地被杂原子间断,和
Z表示氢,表示各任选被取代的烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基烷基、苯氧基烷基、苯基烷基氧基烷基、苯基硫基烷基、苯基烷基硫基烷基、苯基、苯基烷基、杂芳基、杂芳基烷基或表示下列各式基团:—CO2R1;
—SO2R1;—COR1;或氰基,
l表示0-3,
m表示1-3,
n取决于m,表示0-4,
R1表示氢,表示各任选被取代的、饱和或不饱和的烷基或环烷基,其各任选地被杂原子间断,表示各任选被取代的苯基或杂芳基,表示各任选被取代的苯基烷基或杂芳基烷基,
R2表示氢,表示各任选被取代的、饱和或不饱和的烷基或烷氧基,表示各任选被取代的苯基、苯基烷基或苯基烷氧基,或
R1、R2和它们所连的氮原子一起还可以表示任选被取代的环,该环任选地被杂原子间断,
R3表示氢,表示各任选被取代的烷基或烷氧基,表示各任选被取代的苯基或苯基烷基,
R4表示氢或表示任选被取代的烷基,和
R5、R6相互独立地表示氢或表示任选被取代的烷基,
2.根据权利要求1的化合物,其特征在于:
Ar表示Ar1,其中Ar1表示苯基、萘基或具有5-10个环原子的单或双环杂芳基,这些基团各任选地被下列基团一至五取代:卤素、C1-C8-烷基、C2-C8-链烯基、C2-C8-炔基、C1-C8-烷氧基、C2-C8-链烯氧基、C3-C8-炔基氧基、C1-C8-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基、C1-C6-卤代烷氧基、C2-C8-卤代链烯氧基、C1-C2-亚烷基二氧基、C1-C2-卤代亚烷基二氧基、卤代-C1-C4-烷硫基、卤代-C1-C4-烷基亚磺酰基、卤代-C1-C4-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团:a)-L-CO-R7,或表示Ar2,其中Ar2表示额外被苯基、萘基、五或六元杂芳基、苯基-C1-C4-烷基、苯氧基、苯基-S(O)g-、五或六元杂芳氧基或杂芳基-S(O)g-取代的Ar1,其中这些取代基本身各自任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基-至四取代,
K表示氧或硫,
L表示氧或硫,
Y表示卤素、C1-C6-烷基、C1-C4-卤代烷基、C1-C6-烷氧基,表示苯基、苯基-C1-C4-烷基、五或六元杂芳基或五或六元杂芳基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,或表示下式基团:—CO2R1或
或两个相邻的Yn表示五至八元的、饱和或不饱和的环,该环可以被1-3个选自N、O和S的杂原子间断并且可以任选地被卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至三取代,
Z表示氢,表示各任选被氟和/或氯取代的C1-C8-烷基、氰基-C1-C6-烷基、C3-C8-链烯基、C3-C8-炔基、C3-C8-环烷基、C3-C8-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷氧基-C1-C4-烷基,表示苯氧基-C1-C4-烷基、苯基-C1-C4-烷氧基-C1-C4-烷基、苯硫基-C1-C4-烷基、苯基-C1-C4-烷硫基-C1-C4-烷基、苯基、苯基-C1-C4-烷基、五或六元杂芳基、五或六元杂芳基-C1-C4-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基或氰基一至四取代,或表示下列各式基团:—CO2R1;
—SO2R1;—COR1;或氰基,其中
g表示0-2,
l表示0-2,
R1表示氢(但不适用于基团-CO2R1和-SO2R1),表示各任选被氟和/或氯取代的C1-C10-烷基、C2-C10-链烯基、C3-C6-炔基,表示各任选被氟、氯、C1-C4-烷基、C1-C4-烷氧基取代的C3-C8-环烷基或C5-C8-环烯基,其中任选地一个亚甲基可以被氧或硫间断,或表示苯基、吡啶基、噻吩基、嘧啶基、噻唑基、苯基-C1-C4-烷基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R2表示氢,表示各任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-链烯氧基,或表示苯基、苯基-C1-C4-烷基或苯基-C1-C4-烷氧基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R1、R2和它们所连的氮原子一起还表示各任选被C1-C4-烷基取代的五至八元环,其中任选地一个亚甲基可以被氧或硫替代,
R3表示氢,任选被卤素取代的C1-C6-烷基,或表示苯基或苯基C1-C2-烷基,它们各任选地被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R4表示氢或C1-C6-烷基,
R5、R6相互独立地表示氢或表示任选被氟和/或氯取代的C1-C4-烷基,
R7表示各任选被氟和/或氯取代的C1-C10-烷基、C2-C10-链烯基、C3-C10-炔基、C1-C10-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷硫基-C1-C4-烷基,表示各任选被氟和/或氯、C1-C4-烷基、C1-C4-烷氧基取代的C3-C8-环烷基或C3-C8-环烷氧基,其中任选地一个亚甲基可以被氧或硫替代,或表示苯基、苯氧基、苄氧基、五或六元杂芳基或苯基-C1-C4-烷基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R8表示氢或C1-C4-烷基,
R9表示氢,各任选被氟和/或氯取代的C1-C10-烷基、C3-C8-链烯基、C3-C8-炔基、C1-C10-烷氧基、C3-C8-链烯氧基,任选地被氟、氯、C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基,其中任选地一个亚甲基可以被氧或硫替代,或表示苯基、苯基-C1-C4-烷基或苯基-C1-C2-烷氧基,它们各任选被卤素、C1-C6-烷基、C1-C6-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、氰基或硝基一至四取代,
R10表示氢、C1-C6-烷基或C3-C6-链烯基,
R9、R10和它们所连的氮原子一起还表示任选地被C1-C4-烷基取代的五至八元环,其中任选地一个亚甲基可以被氧或硫替代,
m表示1-3,
n取决于m,表示0-3。
3.根据权利要求1的化合物,其特征在于:
K表示氧或硫,
Ar表示Ar1,其中Ar1表示苯基、萘基、喹啉基、噻吩基、嘧啶基、呋喃基、噻唑基、苯并噻唑基、噁唑基、吡唑基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔基、C1-C6-烷氧基、C3-C6-链烯氧基、C3-C6-炔基氧基、C1-C6-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C2-C4-卤代链烯氧基、C1-C2-亚烷基二氧基、C1-C2-卤代亚烷基二氧基、卤代-C1-C2-烷硫基、卤代-C1-C2-烷基亚磺酰基、卤代-C1-C2-烷基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团之一:a)—L—CO—R7,
或表示Ar2,其中Ar2表示额外被苯基、吡啶基、嘧啶基、噻吩基、呋喃基、噻唑基、四唑基、三唑基、苄基、苯氧基、苯基-S(O)g-、吡啶基氧基、嘧啶基氧基、噻唑基氧基、吡啶基-S(O)g-、嘧啶基-S(O)g-或噻唑基-S(O)g-取代的Ar1,其中这些取代基本身任选被氟、氯、溴、C1-C4-烷基、C2-C4-链烯基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基一至三取代,其中g表示0-2,
L表示氧或硫,
Y表示氟、C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基,表示苯基、苯基-C1-C2-烷基、噻唑基甲基、吡啶基甲基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至三取代,或表示下式基团:-CO2R1或
或两个相邻的Yn还表示五至六元的、饱和或不饱和的环,该环可以被选自N、O和S的杂原子间断并且可以任选地被氟、氯、溴、甲基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,
Z表示氢,表示各任选被氟和/或氯取代的C1-C6-烷基、氰基-C1-C3-烷基、C3-C6-链烯基、C3-C8-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C2-烷基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-卤代烷氧基-C1-C2-烷基,表示苯氧基-C1-C2-烷基、苯基-C1-C2-烷氧基-C1-C2-烷基、苯硫基-C1-C2-烷基、苯基-C1-C2-烷硫基-C1-C2-烷基、苯基-C1-C2-烷基、苯基、吡啶基-C1-C2-烷基、噻唑基-C1-C2-烷基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、硝基或氰基一至三取代,或表示下列各式基团:-CO2R1;
-SO2R1;-COR1;或氰基,其中
l表示0-1,
R1表示氢(但不适用于基团-CO2R1和-SO2R1),表示各任选被氟和/或氯取代的C1-C6-烷基、C2-C6-链烯基、C3-C4-炔基,表示任选被氟、氯、C1-C2-烷基、C1-C2-烷氧基取代的C3-C6-环烷基,或表示苯基或苄基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至二取代,
R2表示氢,表示各任选被氟和/或氯取代的C1-C4-烷基、C3-C4-链烯基、C3-C4-炔基、C1-C4-烷氧基、C3-C4-链烯氧基,或表示苯基、苄基或苄氧基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、C1-C2-卤代烷基、C1-C2-卤代烷氧基、氰基或硝基一至二取代,
R1、R2和它们所连的氮原子一起还表示各任选被C1-C2-烷基取代的五或六元环,其中任选地一个亚甲基可以被氧替代,
R3表示氢,表示C1-C4-烷基,或表示苯基或苄基,它们各任选地被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,
R4、R5、R6表示氢、甲基或乙基,
R7表示各任选被氟和/或氯取代的C1-C6-烷基、C2-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C1-C4-烷氧基-C1-C2-烷基、C1-C4-烷硫基-C1-C2-烷基,表示各任选被氟和/或氯、C1-C2-烷基、C1-C2-烷氧基取代的C3-C6-环烷基,其中任选地一个亚甲基可以被氧替代,或表示苯基、苯氧基、苄氧基、噻吩基、呋喃基、吡啶基、嘧啶基、噻唑基、吡唑基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R8表示氢,
R9表示氢,各任选被氟和/或氯取代的C1-C6-烷基、C3-C6-链烯基、C3-C6-炔基、C1-C6-烷氧基、C3-C6-环烷基,其中任选地一个亚甲基可以被氧替代,或表示苯基或苯基-C1-C2-烷基,它们各任选被氟、氯、溴、C1-C4-烷基、C1-C4-烷氧基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基或硝基一至二取代,
R10表示氢或C1-C4-烷基,
R9、R10和它们所连的氮原子一起还表示任选地被C1-C2-烷基取代的五至六元环,其中任选地一个亚甲基可以被氧替代,
m表示0-1,
n取决于m,表示0-2。
4.根据权利要求1的化合物,其特征在于:
K表示氧或硫,
Ar表示Ar1,其中Ar1表示苯基、噻吩基、嘧啶基、呋喃基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、烯丙氧基、甲基烯丙氧基、2-丁烯氧基、炔丙氧基、2-丁炔氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、巯基、硝基、氰基、氨基或下列各式基团之一:a)—L—CO—R7,
或表示Ar2,其中Ar2表示额外被苯基、吡啶基、噻吩基、四唑基、三唑基或苯氧基取代的Ar1,其中这些取代基本身任选被氟、氯、溴、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、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基一至二取代,和
L表示氧或硫,
X表示—CN,—CO—NH2,
Y表示甲基,表示苯基,它任选被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基一至三取代,或表示基团-CO2R1,或
两个相邻的Yn还可以表示六元的不饱和的环,该环可以任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基单取代,
Z表示氢、甲基、乙基、烯丙基、炔丙基、环丙基、环戊基、环己基、环丙基甲基、环戊基甲基、环己基甲基、甲氧基甲基、乙氧基甲基,表示苯基、苄基、吡啶基甲基、噻唑基甲基,它们各任选地被氟、氯、溴、甲基、甲氧基、三氟甲基或三氟甲氧基、硝基或氰基一至二取代,或表示下列各式基团:—CO2R1,
—SO2R1,—CO-R1,或氰基,其中
R1表示氢(但不适用于基团-CO2R1和-SO2R1)、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、炔丙基、环丙基、环戊基、环己基,或表示苯基或苄基,它们各任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,
R2表示氢、甲基、乙基、丙基、异丙基、烯丙基、炔丙基、甲氧基、乙氧基、烯丙氧基,或表示苄氧基,它任选地被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,或
R1、R2和它们所连的氮原子一起表示吡咯烷、噻嗪、哌啶或吗啉基团,
R3、R5各表示氢、甲基或乙基,
R7表示甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、乙烯基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、环丙基、环戊基、环己基、环戊基氧基、环己基氧基,表示苯基、吡啶基或苄基,它们各任选被氟、氯、溴、甲基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,或者,在Ar下所提及的基团a)和c)的情况下,也表示基团或者,对于基团g),也表示羟基,
R9表示氢、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基、环戊基、环己基,表示苯基,它任选被氟、氯、溴、甲基、甲氧基、三氟甲基、三氟甲氧基、氰基或硝基一至二取代,
R10表示氢、甲基或乙基,或
R9、R10和它们所连的氮原子一起表示吡咯烷、哌啶或吗啉基团,
m表示1-3,
n取决于m,表示0-1。
5.根据权利要求1的化合物,其特征在于:
K表示氧或硫,
Ar表示Ar1,其中Ar1表示苯基、噻吩基、嘧啶基或吡啶基,这些基团各任选地被下列基团一至三取代:氟、氯、溴、甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、烯丙氧基、甲基烯丙氧基、2-丁烯氧基、炔丙氧基、2-丁炔氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、三氟甲基、二氟甲氧基、三氟甲氧基、亚甲基二氧基、二氟亚甲基二氧基、四氟亚乙基二氧基、二氟甲硫基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基、羟基、硝基、巯基、氰基、氨基,
或表示Ar2,其中Ar2表示额外被苯基或苯氧基取代的Ar1,其中这些取代基本身任选被氟、氯、溴、甲基、乙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、甲氧基、乙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲基、三氟甲氧基、硝基或氰基一至二取代,
X表示CN,
Z表示氢或甲基,
m表示1-3,
n表示0。
6.制备权利要求1-5任一项的化合物的方法,其特征在于:
Y、m、n各如权利要求1-5任一项中所定义,
W表示O或S(O)g,其中g表示0或2,和
R11表示烷基或苄基,该反应任选地在稀释剂存在下和任选地在碱或下式(IIIa)的金属化合物存在下进行,
Me(V)2 (IIIa)其中
Me表示二价过渡金属原子,和
V表示螯合物配位体,或
B)在K表示氧和Z表示氢的情况下,任选地在稀释剂存在下,使式(IV)化合物与式(V)化合物反应,其中
Ar和X各如权利要求1-5任一项中所定义,和
Ar、X、Y、m和n各如权利要求1-5任一项中所定义,
该化合物进一步任选地在碱存在下和任选地在三价磷化合物存在下进行反应消除硫和卤化氢,得到其中Ar、X、Y、m和n各如权利要求1-5任一项中所定义和Z表示氢的式(I)化合物,或
C)在K表示氧和Z不是氢的情况下,任选地在稀释剂存在下,使式(VII)化合物与卤化剂反应,其中
Y、Z、m和n各如权利要求1-5任一项中所定义,和
Z不是氢,和
Ar、X各如权利要求1-5任一项中所定义,或
D)在K表示氧但是Z不是氢的情况下,任选地在溶剂存在下和任选地在碱存在下,使式(I-a)化合物与式(IX)的烷化剂、酰化剂、磺酰化剂或缩合剂反应,其中
Ar、X、Y、m和n各如权利要求1-5任一项中所定义,
Z-G (IX),其中
G表示离去基团诸如卤素、磺酸酯基或烷氧基,或E)在Ar代表权利要求1-5任一项中所定义的Ar2的情况下,在溶剂存在下和任选地在碱和/或贵金属配合物存在下,使式(I1)化合物与式(X)的硼酸反应,其中
Ar1、X、Y、Z、m和n各如权利要求1-5任一项中所定义,和
Hal表示卤素,
Ar2—B(OH)2 (X),其中
Ar2如在权利要求2-5任一项中所定义,
Ar、X、Y、Z、m和n各如权利要求1-5任一项中所定义,和
K表示氧。
7.除草、杀螨和/或杀虫组合物,其特征在于,它们含有至少一种权利要求1-5任一项的化合物。
8.权利要求1-5任一项的化合物防治不想要的植物和/或动物害虫的应用。
10.式(II-1-b)的化合物,其中
T如下表中所定义:
T
3-Cl,4-F
4-Cl,3-F
3,5-(CF3)2
2,4-Cl2,5-F
3,5-Cl2,4-F
4-Cl,2-F
3-CF3,5-CH3
3-Cl,4,5-F2
4-CN,2,5-F2
2,3-F2
3-F,4-CF3
3,4-O-CF2-O
3-NO2,5-CF3
4-Cl,2,5-F2
3,4,5-(OC2H5)3
4-Br.2-F
2,6-Cl2,4-CF3
2-F,4-NO2
2,4-Cl2,5-NO2
4-Cl,2-F,5-NO2
2,4-F2,5-NO2
4-Br,2-F,5-NO2
2-F,4-CF3
4-OCF3,3-NO2
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DE19851986A DE19851986A1 (de) | 1998-11-11 | 1998-11-11 | Phenyl-substituierte zyklische Enaminone |
DE19851986.9 | 1998-11-11 |
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EP (1) | EP1129071B1 (zh) |
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KR (1) | KR100646082B1 (zh) |
CN (1) | CN1325472C (zh) |
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DE (2) | DE19851986A1 (zh) |
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HK (1) | HK1042702A1 (zh) |
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CN111848450A (zh) * | 2019-04-30 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 一种新的取代的烯胺化合物及其制备方法 |
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DE10021900A1 (de) * | 2000-05-08 | 2001-11-15 | Bayer Ag | Phenyl-substituierte 2-Enamino-Ketonitrile |
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CA2523426C (en) | 2003-04-24 | 2013-02-26 | Incyte Corporation | Aza spiro alkane derivatives as inhibitors of metalloproteases |
DE102004049041A1 (de) * | 2004-10-08 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
US7910108B2 (en) * | 2006-06-05 | 2011-03-22 | Incyte Corporation | Sheddase inhibitors combined with CD30-binding immunotherapeutics for the treatment of CD30 positive diseases |
WO2012116246A2 (en) * | 2011-02-25 | 2012-08-30 | Dow Agrosciences Llc | Pesticidal compostions and processes related thereto |
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US11589583B2 (en) * | 2013-12-03 | 2023-02-28 | Fmc Corporation | Pyrrolidinones herbicides |
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MX2018011216A (es) | 2016-03-16 | 2019-08-29 | H Lee Moffitt Cancer Ct & Res | Moléculas pequeñas contra cereblon para mejorar la función efectora de los linfocitos t. |
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WO2024005032A1 (ja) * | 2022-06-29 | 2024-01-04 | 株式会社Adeka | アゼパンジオン誘導体又はその塩類及び該化合物を含有する有害生物防除剤並びにその使用方法 |
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DE2920183A1 (de) * | 1979-05-17 | 1981-04-30 | Schering Ag Berlin Und Bergkamen, 1000 Berlin | Thiazolyliden-oxo-propionitrile, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
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-
1998
- 1998-11-11 DE DE19851986A patent/DE19851986A1/de not_active Withdrawn
-
1999
- 1999-11-02 DE DE59912719T patent/DE59912719D1/de not_active Expired - Fee Related
- 1999-11-02 PL PL99348763A patent/PL348763A1/xx not_active Application Discontinuation
- 1999-11-02 EP EP99955944A patent/EP1129071B1/de not_active Expired - Lifetime
- 1999-11-02 BR BR9915260-6A patent/BR9915260A/pt not_active IP Right Cessation
- 1999-11-02 KR KR1020017004969A patent/KR100646082B1/ko not_active IP Right Cessation
- 1999-11-02 ES ES99955944T patent/ES2247838T3/es not_active Expired - Lifetime
- 1999-11-02 US US09/831,261 patent/US6455472B1/en not_active Expired - Fee Related
- 1999-11-02 RU RU2001116103/04A patent/RU2001116103A/ru not_active Application Discontinuation
- 1999-11-02 CN CNB99813208XA patent/CN1325472C/zh not_active Expired - Fee Related
- 1999-11-02 AU AU12688/00A patent/AU770205B2/en not_active Ceased
- 1999-11-02 WO PCT/EP1999/008366 patent/WO2000027812A1/de active IP Right Grant
- 1999-11-02 AT AT99955944T patent/ATE307800T1/de not_active IP Right Cessation
- 1999-11-02 CA CA002350305A patent/CA2350305A1/en not_active Abandoned
- 1999-11-02 JP JP2000580992A patent/JP2002529450A/ja not_active Withdrawn
- 1999-11-11 AR ARP990105739A patent/AR021150A1/es not_active Application Discontinuation
-
2002
- 2002-06-04 HK HK02104242.6A patent/HK1042702A1/zh unknown
- 2002-07-26 US US10/206,426 patent/US20030130125A1/en not_active Abandoned
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102048718A (zh) * | 2009-11-02 | 2011-05-11 | 王泽君 | 烯胺酮类化合物的医疗应用 |
CN111848450A (zh) * | 2019-04-30 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 一种新的取代的烯胺化合物及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
PL348763A1 (en) | 2002-06-03 |
EP1129071B1 (de) | 2005-10-26 |
CA2350305A1 (en) | 2000-05-18 |
RU2001116103A (ru) | 2003-04-20 |
US6455472B1 (en) | 2002-09-24 |
CN1325472C (zh) | 2007-07-11 |
BR9915260A (pt) | 2001-08-07 |
HK1042702A1 (zh) | 2002-08-23 |
AU770205B2 (en) | 2004-02-19 |
KR100646082B1 (ko) | 2006-11-13 |
DE19851986A1 (de) | 2000-05-18 |
AR021150A1 (es) | 2002-06-12 |
KR20010085944A (ko) | 2001-09-07 |
DE59912719D1 (de) | 2005-12-01 |
AU1268800A (en) | 2000-05-29 |
JP2002529450A (ja) | 2002-09-10 |
ES2247838T3 (es) | 2006-03-01 |
EP1129071A1 (de) | 2001-09-05 |
US20030130125A1 (en) | 2003-07-10 |
WO2000027812A1 (de) | 2000-05-18 |
ATE307800T1 (de) | 2005-11-15 |
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