CN1454206A - 苯基-取代的2-烯胺基-酮腈 - Google Patents
苯基-取代的2-烯胺基-酮腈 Download PDFInfo
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- CN1454206A CN1454206A CN01812492A CN01812492A CN1454206A CN 1454206 A CN1454206 A CN 1454206A CN 01812492 A CN01812492 A CN 01812492A CN 01812492 A CN01812492 A CN 01812492A CN 1454206 A CN1454206 A CN 1454206A
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- methyl
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- 238000000034 method Methods 0.000 claims abstract description 80
- -1 sulfydryl Chemical group 0.000 claims description 307
- 150000001875 compounds Chemical class 0.000 claims description 189
- 239000001257 hydrogen Substances 0.000 claims description 132
- 229910052739 hydrogen Inorganic materials 0.000 claims description 132
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 107
- 239000011737 fluorine Substances 0.000 claims description 93
- 229910052731 fluorine Inorganic materials 0.000 claims description 93
- 229910052760 oxygen Inorganic materials 0.000 claims description 92
- 239000001301 oxygen Substances 0.000 claims description 90
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 88
- 239000000460 chlorine Substances 0.000 claims description 85
- 229910052801 chlorine Inorganic materials 0.000 claims description 85
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 83
- 150000002431 hydrogen Chemical class 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 68
- 239000002585 base Substances 0.000 claims description 64
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 63
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 61
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 57
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 56
- 229910052794 bromium Inorganic materials 0.000 claims description 56
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 55
- 238000002360 preparation method Methods 0.000 claims description 53
- 239000002904 solvent Substances 0.000 claims description 50
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 48
- 239000005864 Sulphur Chemical group 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 28
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 27
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 24
- 239000003513 alkali Substances 0.000 claims description 23
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 17
- 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 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005336 allyloxy group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 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 8
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 8
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- VAKKJWXZRREDEX-UHFFFAOYSA-N [O].CC#CC Chemical compound [O].CC#CC VAKKJWXZRREDEX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 5
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- COOBQCQBQKKKIZ-UHFFFAOYSA-N difluoro-methylperoxy-(trifluoromethylperoxy)methane Chemical group FC(OOC(F)(F)F)(OOC)F COOBQCQBQKKKIZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000003222 pyridines Chemical class 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
- 239000000642 acaricide Substances 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 239000003446 ligand Substances 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 150000003624 transition metals Chemical group 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
- 125000005554 pyridyloxy group Chemical group 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 3
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 230000002363 herbicidal effect Effects 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 20
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 238000005987 sulfurization reaction Methods 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 2
- 229910052727 yttrium Inorganic materials 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 5
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- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 235000011351 tree mallow Nutrition 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-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
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-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
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 241000701451 unidentified granulovirus Species 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A 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-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 239000010457 zeolite 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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- C07D211/06—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 no double bonds between ring members or between ring members and non-ring members
- C07D211/36—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 no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
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- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- 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
- C07C255/42—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 singly-bound nitrogen atoms, not being further bound to other hetero atoms
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- 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
- C07C255/42—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 singly-bound nitrogen atoms, not being further bound to other hetero atoms
- C07C255/43—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 singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
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Abstract
本发明涉及新的式(I)的苯基取代的2-烯胺基-酮腈:如式(1),其中Ar,X,Z,Y和K各自如说明书中所述定义。本发明还涉及所述苯基取代的2-烯胺基-酮腈的多种制备方法和它们作为除草剂和杀虫剂的用途。
Description
本发明涉及新的苯基-取代的2-烯胺基-酮腈,它们的多种制备方法以及它们作为农作物保护剂的用途,特别是用作除草剂,杀螨剂,杀线虫剂和杀虫剂。
某些在苯环上被取代的且具有除草活性的2-烯胺基-酮腈已经公开在,例如EP-A0348002中。然而,至今这些2-[3-苯氧基-或3-[(2-吡啶氧基)苯甲酰基]-3-(二烷基氨基)丙烯腈-]还没有达到有意义的地步。
同样公开在JP-A210175937,WO99/16753和EP-A0490220中的具有除草活性的各化合物也不具有有价值的意义。
而且,已公开了可用作合成抗菌活性化合物的中间体的2-烯胺基-酮腈,参见DE-A3502935,EP-A0220523,DE3426483和EP-A0168737中。
其它2-烯胺基-酮腈还公开在DE-A19958164,DE-A19851986,DE-A10007286和WO00/27812中。
还公开了在苯环上未取代的2-烯胺基-酮腈(I.N.Sobhy,H.S.Zahi,M.M.Has san,E.M.Hilmy,(Chem.Ind.(伦敦),1988,
17,563-564),I.N.Sobhy,M.M.Hassan,E.M.Hilmy(Arch.Pharm.1987,320(6),487-491),E.A.Ghani,M.A.Fathy,F.A.Amer,Collet.Czech,Chem.Commun.(1986,
51,2193-2198),C.Degrand,G.Belot,P-L.Compagnon,F.Jasquez,Can.J.Chem.(1983,
61,2581-2589),E.M.Hilmy,M.S.Fahmy,E.A.A.Hafez,R.M.ElmoghayarJ.Heterocyl.Chem.(1979,
16,1109-1111),H.Schfer,K.Gewald,Monatsh.Chem.(1978),
109,527-535)。M.Savkar,S.Chattopadhyay,K.K.Mahalanabis,Ind.J.Chem.Sect.B(1996,
25B,1133-1137)。Z.E.S.Kandeel,F.M.Abelrazeh,M.E.Eldin,J.Chem.Soc.Perk.Trans.1(1985,
7,1499-1501),H.Jurek,H.W.Schmidt,G.Gfrerer,Synthesis,(1982,
9,791)K.Gewald,H.Schfer,K.Sattler,Monatsh.Chem.(1979,
110,1189)。
迄今还没有公开这些化合物作为植物保护剂的用途。
式(I)提供了新的2-烯胺基-酮腈的通式定义其中
K代表氧或硫,
Ar代表各自任选取代的苯基,萘基,或代表各自任选取代的具有5-10个环原子的单-或双环的杂芳基,或代表基团其中
B1代表氢或卤素,
两个相邻基团-B2和B3或B3和B4-一起代表下列基团之一
-Q1-CQ2-,-Q1-CQ2-Q3-,-Q1-C(B6,B7)-Q3-,-C(B6,B7)-CQ2-,
-C(B6,B7)-Q1-CQ2-,-Q1-C(B6,B7)-C(B6,B7)-,
-Q1-C(B6,B7)-C(B6,B7)-Q3-,-C(B6,B7)-C(B6,B7)-CQ2-,
-Q1-C(B6)=C(B6)-,-C(B6)=C(B6)-CQ2-,-Q1-C(B6,B7)-CQ2-,
-N(B8)-C(B6,B7)-CQ2-,-C(B6)=N-,-Q1-CQ2-C(B6,B7)-,
-Q1-CQ2-N(B8)-,-Q1-C(B6,B7)-CQ2-N(B8)-,
-C(B6,B7)-Q1-CQ2-N(B8)-,-C(B6,B7)-C(B6,B7)-N(B8)-,
-C(B6,B7)-C(B6,B7)-CQ2-N(B8)-,-C(B6)=C(B6)-N(B8)-,
-C(B6)=C(B6)-CQ2-N(B8)-,-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-C(B6,B7)-CQ2-N(B8)-,-C(B6)=N-N(B8)-,
-Q1-CQ2-C(B6,B7)-N(B8)-,-Q1-C(B6,B7)-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-CQ2-C(B6)=N-,-Q1-C(B6)=C(B6)-Q3-,
-N(B8)-C(B6)=C(B6)-CQ2-,
-N(B8)-C(B6)=N-,-N(B8)-C(B6,B7)-C(B6,B7)-Q3-,
-N(B8)-CQ2-C(B6,B7)-Q4-,-N(B8)-CQ2-CQ2-Q3-,
-Q1-C(B6)=C(B6)-C(B6,B7)-,-Q1-C(B6)=C(B6)-,以及第四个基团,B4或B2,代表氢,硫代氨甲酰基,氰基或卤素,
其中
Q1,Q2和Q3可以相同或不同,并各自代表氧或硫,和
Q4代表-SO-或-SO2-,
B6和B7可以相同或不同并各自地代表氢,卤素或烷基或一起代表链烷二基,和
B8代表氢,羟基,代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基-取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选被卤素取代的烯基或炔基,代表各自任选被卤素或烷基-取代的环烷基或环烷基烷基,代表各自任选卤素取代的烷氧基或烯氧基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基或芳烷氧基,
Y代表氢,代表各自任选取代的烷基,烯基,炔基,烷氧基烷基,烷硫基烷基,代表各自任选取代的环烷基或环烷基烷基,上述的环烷基或环烷基烷基各自任选在其环上被杂原子间断,或代表各自任选取代的苯基烷基或杂芳基烷基,
Z代表氢,代表各自任选取代的烷基,苯基或苯基烷基,
R1代表氢,代表各自任选取代的饱和或不饱和的、各自任选被杂原子间断的烷基或环烷基,代表各自任选取代的苯基或杂芳基,代表各自任选取代的苯基烷基或杂芳基烷基,和
R2代表氢,代表各自任选取代的、饱和或不饱和的烷基或烷氧基,代表各自任选取代的苯基,苯基烷基或苯基烷氧基,或
R1,R2还与它们所连接的氮原子一起代表任选取代的环,该环任选被一个或多个杂原子间断。
式(I)化合物中,下列化合物是适用的:
Ar优选代表Ar1,其中Ar1代表苯基,萘基或具有五至十个环原子的单-或双环的杂芳基,各基团各自任选被下列基团一-至五取代:卤素,C1-C8-烷基,C2-C8-烯基,C2-C8-炔基,C1-C8-烷氧基,C2-C8-烯氧基,C3-C8-炔氧基,C1-C8-烷硫基,C1-C6-烷基磺酰基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C2-C8-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C4-烷硫基,卤代-C1-C4-烷基磺酰基,苯基-C1-C4-烷氧基,羟基,巯基,硝基,氰基,氨基或下述基团
a)-L-CO-R3,或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,萘基,五-或六员杂芳基,苯基-C1-C4-烷基,苯氧基,苯基-S(O)g-,五或六员杂芳氧基或杂芳基-S(O)g,其中就其本身来说这些取代基各自任选被下列基团一-至四取代:卤素,C1-C6-烷基,C1-C6-烯基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基,其中g代表0,1或2,
B1代表氢或卤素,
两个相邻的基团-B2和B3或B3和B4-一起代表下列基团之一
-Q1-CQ2-N(B8)-,-Q1-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-C(B6,B7)-CQ2-N(B8)-,-Q1-CQ2-C(B6,B7)-N(B8)-,
-Q1-C(B6)=C(B6)-C(B6,B7)-,-Q1-C(B6)=C(B6)-,
-N(B8)-CQ2-C(B6)=N-其中
Q1和Q2可以相同或不同并各自代表氧或硫,
B6和B7可以相同或不同并各自代表氢或甲基,
B8代表氢,羟基,代表各自任选氰基-,氟-,氯-,甲氧基-,乙氧基-,乙酰基-,丙酰基-,甲氧基羰基-或乙氧基羰基-取代的甲基,乙基,正-或异丙基,正-,异-,仲-或叔丁基,代表各自任选氟-,氯-或溴取代的丙烯基,丁烯基,丙炔基或丁炔基,代表各自任选氟-,氯-,溴-,甲基-或乙基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,代表各自任选氟-和/或氯-取代的甲氧基,乙氧基,正-或异丙氧基,正-,异-或仲丁氧基,丙烯氧基或丁烯氧基,或代表各自任选氰基-,氟-,氯-,甲基-,乙基-,三氟甲基-,甲氧基-,乙氧基-,二氟甲氧基-或三氟甲氧基取代的苄基或苄氧基,
和第四个基团,B4或B2,代表氢,氰基,氟或氯,
K优选代表氧或硫。
L优选代表氧或硫。
Y优选代表氢,各自任选一-或多羟基取代的C1-C12-烷基,C3-C10-烯基,C3-C10-炔基,C1-C6-烷氧基-C2-C4-烷基,二-C1-C6-烷氧基-C2-C4-烷基,C1-C6-烷氧基-C2-C4-氰基烷基,C1-C6-烷硫基-C2-C4-烷基,C1-C8-卤代烷基,C1-C8-卤代烯基或C1-C8-氰基烷基,代表各自任选下列基团取代的任选环上被氧,硫或氮间断的C3-C8-环烷基或C3-C8-环烷基-C1-C4-烷基:C1-C6-烷基-,C1-C6-烷氧基-,C1-C4-卤代烷基-,氰基-,卤代苯基-,苄基-,C1-C6-羟基烷基-或卤素,代表苯基-C1-C4-烷基或五-或六员杂芳基-C1-C4-烷基,各基团任选被卤素,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。
Z优选代表氢,C1-C6-烷基,代表苯基或苯基-C1-C4-烷基,各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基一至三取代。
R1优选代表氢,代表各自任选氟-和/或氯取代的C1-C10-烷基,C3-C10-烯基,C3-C6-炔基,代表各自任选氟-,氯-,C1-C4-烷基-,C1-C4-烷氧基-取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C5-C8-环烯基,或代表苯基,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,各基团任选被卤素,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。
R2优选代表氢,C1-C6-烷基或C3-C6-烯基。
R1,R2还优选与它们所连接的氮原子一起代表各自任选C1-C4-烷基取代的五-至八员环,其中任选一个亚甲基可被氧或硫替换。
R3优选代表各自任选氟-和/或氯取代的C1-C10-烷基,C2-C10-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,各自任选氟-和/或氯-,C1-C4-烷基-,C1-C4-烷氧基取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C3-C8-环烷氧基,代表苯基,苯氧基,苄氧基,五-或六员杂芳基或苯基-C1-C4-烷基,各基团任选被卤素,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,或当Ar中所述基团a),c)和f)的情况下,还代表下列基团
R4优选代表氢或C1-C4-烷基。
R5优选代表氢或任选氟-和/或氯取代的C1-C4-烷基。
R6优选代表氢,各自任选氟-和/或氯取代的C1-C10-烷基,C3-C8-烯基,C3-C8-炔基,C1-C10-烷氧基,C3-C8-烯氧基,任选下列基团取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基:氟-,氯-,C1-C4-烷基-或C1-C4-烷氧基-,代表苯基,苯基-C1-C4-烷基或苯基-C1-C2-烷氧基,各基团任选被卤素,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。
R7优选代表氢,C1-C6-烷基或C3-C6-烯基。
R6,R7还优选与它们所连接的氮原子一起代表任选C1-C4-烷基取代的五-至八员环,其中,任选一个亚甲基可被氧或硫替换。
K特别优选代表氧或硫。
Ar特别优选代表Ar1,其中Ar1代表苯基,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,各基团任选被下列基团一-至三取代:氟,氯,溴,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-烷氧基,C3-C6-烯氧基,C3-C6-炔氧基,C1-C6-烷硫基,C1-C4-烷基磺酰基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,C2-C4-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C2-烷硫基,卤代-C1-C2-烷基磺酰基,苯基-C1-C4-烷氧基,羟基,巯基,硝基,氰基,氨基或下列基团之一或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1: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-,吡啶氧基,嘧啶氧基,噻唑氧基,吡啶基-S(O)g,嘧啶基-S(O)g-或噻唑基-S(O)g-,其中就其本身来说这些取代基任选被下列基团一-至三取代:氟,氯,溴,C1-C4-烷基,C2-C4-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,其中g代表0,1或2,
或代表基团其中
B1代表氢或卤素,
两个相邻基团-B2和B3或B3和B4-一起代表下列基团
-Q1-C(B6,B7)-CQ2-N(B8)-,其中
Q1和Q2相同或不同并各自代表氧或硫,
B6和B7相同和不同并各自代表氢或甲基,
B8代表氢,羟基,代表各自任选氰基-,氟-,氯-,甲氧基-,乙氧基-,乙酰基-,丙酰基-,甲氧基羰基-或乙氧基羰基-取代的甲基,乙基,正或异丙基,正-,异-,仲或叔丁基,代表各自任选氟-,氯-或溴-取代的丙烯基,丁烯基,丙炔基或丁炔基,代表各自任选氟-,氯-,溴-,甲基-或乙基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,代表各自任选氟-和/或氯-取代的甲氧基,乙氧基,正-或异丙氧基,正-,异-或仲丁氧基,丙烯氧基或丁烯氧基,或代表各自任选氰基-,氟-,氯-,甲基-,乙基-,三氟甲基-,甲氧基-,乙氧基-,二氟甲氧基或三氟甲氧基取代的苄基或苄氧基,
和第四个基团,B4或B2,代表氢,氰基,氟或氯,
Y特别优选代表氢,代表各自任选一-或多羟基取代的C1-C10-烷基,C1-C6-卤代烷基,C3-C8-烯基,C3-C8-炔基,C1-C4-烷氧基-C2-C3-烷基,二-C1-C4-烷氧基-C2-C4-烷基,C1-C4-烷氧基-C2-C4-氰基烷基,C1-C4-烷硫基-C2-C3-烷基,C1-C6-卤代烯基或C1-C6-氰基烷基,代表各自任选下列基团取代的、任选一个亚甲基可被氧或氮替换的C3-C6-环烷基或C3-C6-环烷基-C1-C2-烷基:C1-C4-烷基-,C1-C4-烷氧基-,C1-C2-卤代烷基-,氰基-,卤代苯基-,苄基-,C1-C4-羟基烷基-,氟-或氯,代表苯基-C1-C3-烷基,噻唑基甲基,三唑基甲基或吡啶基甲基,各自任选被下列基团一-至三取代: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。
Z特别优选代表氢,C1-C3-烷基,代表各自任选被下列基团一-至二取代的苯基或苄基: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。
R1特别优选代表氢,代表各自任选氟和/或氯取代的C1-C6-烷基,C2-C6-烯基,C3-C4-炔基,代表任选氟-,氯-,C1-C2-烷基-,C1-C2-烷氧基-取代的C3-C6-环烷基或代表各自任选被下列基团一-至二取代的苯基或苄基: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。
R2特别优选代表氢,代表各自任选被氟和/或氯取代的C1-C4-烷基或C3-C4-烯基。
R1,R2还特别优选与它们所连接的氮原子一起代表任选甲基取代的五-至六员环,其中任选一个亚甲基可被氧替换,
R3特别优选代表各自任选氟-和/或氯-取代的C1-C6-烷基,C2-C6-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,各自任选氟-和/或氯-,C1-C2-烷基-,C1-C2-烷氧基取代的、任选一个亚甲基可被氧替换的C3-C6-环烷基或C3-C6-环烷氧基,代表各自任选被下列基团一-至二取代的苯基,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: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,或在Ar中所列的基团a),c)和f)情况下,还代表基团
R4特别优选代表氢。
R5特别优选代表氢,甲基或乙基。
R6特别优选代表氢,各自任选氟-和/或氯-取代的C1-C6-烷基,C3-C6-烯基,C3-C6-炔基,C1-C6-烷氧基,C3-C6-环烷基,其中任选一个亚甲基可被氧替换,代表各自任选被下列基团一-至二取代的苯基或苯基-C1-C2-烷基: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。
R7特别优选代表氢或C1-C4-烷基。
R6,R7还特别优选与它们连接的氮原子一起代表任选C1-C2-烷基-取代的五-至六员环,该环中任选一个亚甲基可被氧替换。
K更特别优选代表氧或硫。
Ar更特别优选代表Ar1,其中Ar1代表任选被下列基团一-至三取代的苯基:氟,氯,溴,甲基,乙基,丙基,异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,丙氧基,异丙氧基,仲-,正-,异-或叔丁氧基,烯丙氧基,甲代烯丙氧基(Methallyloxy),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,亚甲二氧基,二氟亚甲二氧基,四氟亚乙二氧基,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,苄氧基,羟基,巯基,硝基,氰基或氨基,或代表任选被下列基团一-至二取代的吡啶基:氟,氯,溴,甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,甲硫基,乙硫基或三氟甲基,
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,吡啶基,噻吩基,四唑基,三唑基或苯氧基,其中就其本身来说这些取代基还任选被下列基团一-至二取代:氟,氯,溴,甲基,乙基,正-或异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,异丙氧基,仲-,正-或叔丁氧基,三氟甲基,三氟甲氧基,硝基或氰基,
或代表基团
其中B1代表氢或氟和B8代表烯丙基,炔丙基或苄基,
Y更特别优选代表氢,各自任选一-或多羟基取代的C1-C6-烷基,C1-C4-卤代烷基,C3-C6-烯基,C3-C6-炔基,C1-C4-烷氧基-C2-C3-烷基,二-C1-C2-烷氧基-C2-C4-烷基,C1-C2-烷氧基-C2-C4-氰基烷基,C1-C2-烷硫基-C2-C3-烷基,C1-C5-卤代烯基或C1-C6-氰基烷基,代表各自任选甲基-,甲氧基-,乙氧基-,三氟甲基-,氰基-,氯苯基-,苄基-,羟甲基-,氟-或氯-取代的、其中任选一个亚甲基可被氧或硫替换的C3-C6-环烷基或C3-C6-环烷基-C1-C2-烷基,代表各自任选被下列基团一-至三取代的苄基,苯乙基或吡啶甲基:氟,氯,溴,甲基,甲氧基,三氟甲基,二氟甲氧基,三氟甲氧基,氰基或硝基。
Z更特别优选代表氢,甲基,乙基,代表各自任选被下列基团一-或二取代的苯基或苄基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基。
R3更特别优选代表甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,乙烯基,三氟甲基,甲氧基,乙氧基,丙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,环丙基,环戊基,环己基,环戊氧基,环己氧基,代表各自任选被下列基团一-至二取代的苯基,吡啶基或苄基:氟,氯,溴,甲基,正-,仲-,异-或叔丁基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基,或在Ar中所列的基团a),c)和f)的情况下,还代表基团
R5更特别优选代表氢或甲基。
R6更特别优选代表氢,甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,环丙基,环戊基,环己基,代表任选被下列基团一-至二取代的苯基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基。
R7更特别优选代表氢,甲基或乙基。
R6,R7与它们连接的氮原子一起更特别优选代表吡咯烷基,哌啶基或吗啉基。
K尤其优选代表氧。
Ar尤其优选代表Ar1,其中Ar1代表任选被下列基团一-至三取代的苯基:氟,氯,溴,甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,甲氧基,乙氧基,丙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,烯丙氧基,甲代烯丙氧基,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,亚甲二氧基,二氟-亚甲二氧基,四氟亚乙二氧基,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,苄氧基,羟基,硝基,巯基,氰基或氨基,或代表任选被下列基团一-或二取代的吡啶基:氟,氯,溴,甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基或三氟甲基,
或代表Ar2,其中Ar2代表另外被苯基或苯氧基取代的Ar1,其中就其本身来说这些取代基任选被下列基团一-或二取代:氟,氯,溴,甲基,乙基,异丙基,正-,仲-,异或叔丁基,甲氧基,乙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,三氟甲基,三氟甲氧基,硝基或氰基。
Ar最优选代表被下列基团一-或多取代的苯基:三氟甲基,氟,氯,烯丙氧基,氰基,苄氧基或代表基团其中特别优选的定义是4-氯苯基,3,5-二(三氟甲基)苯基和2-氟-4-氯-5-烯丙氧基。
X尤其优选代表CN。
Y尤其优选代表氢,C1-C6-烷基,C1-C3-卤代烷基,环丙基,环戊基,环己基,环丙基甲基,环戊基甲基和环己基甲基。
Z尤其优选代表氢或甲基。
同样特别提及的还包括下列一个亚组的式(I)化合物:
通式(I)‘的2-烯胺基-酮腈其中
K代表氧或硫,
Ar代表各自取代的苯基,萘基或代表各自任选取代的具有5-10个环原子的单或双环杂芳基,
Y代表氢,代表各自任选取代的烷基,烯基,烷氧基烷基,烷硫基烷基,代表各自任选取代的、环上被杂原子间断的环烷基或环烷基烷基或代表任选取代的苯基烷基或杂芳基烷基,
Z代表氢,代表各自任选取代的烷基,苯基或苯基烷基,
R1代表氢,代表各自任选取代的饱和或不饱和的、任选被杂原子间断的烷基或环烷基,代表各自任选取代的苯基或杂芳基,代表各自任选取代的苯基烷基或杂芳基烷基,和
R2代表氢,代表各自任选取代的饱和或不饱和的烷基或烷氧基,代表各自任选取代的苯基,苯基烷基或苯基烷氧基,或
R1,R2还与它们连接的氮原子一起代表任选取代的环,该环可任选被杂原子间断。
对于式(I)‘化合物,下列化合物是适合的:
Ar优选代表Ar1,其中Ar1代表苯基,萘基或具有五至十个环原子的单或双环杂芳基,各基团任选被下列基团一-至五取代:卤素,C1-C8-烷基,C2-C8-烯基,C2-C8-炔基,C1-C8-烷氧基,C2-C8-烯氧基,C3-C8-炔氧基,C1-C8-烷硫基,C1-C6-烷基磺酰基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C2-C8-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C4-烷硫基,卤代-C1-C4-烷基磺酰基,羟基,巯基,硝基,氰基,氨基或基团
a)-L-CO-R3,
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,萘基,五-或六员杂芳基,苯基-C1-C4-烷基,苯氧基,苯基-S(O)g-,五-或六员杂芳氧基或杂芳基-S(O)g,其中就其本身来说这些取代基各自任选被下列基团一-至四取代: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,其中g代表0,1或2。
K优选代表氧或硫。
L优选代表氧或硫。
X优选代表CN,
或
Y优选代表氢,C1-C12-烷基,C3-C10-烯基,C1-C6-烷氧基-C2-C4-烷基,C1-C6-烷硫基-C2-C4-烷基,C1-C8-卤代烷基,代表各自任选C1-C6-烷基-,C1-C6-烷氧基-,C1-C4-卤代烷基-或卤素取代的、任选环上被氧或硫间断的C3-C8-环烷基或C3-C8-环烷基-C1-C4-烷基,代表各自任选被下列基团一-至四取代的苯基-C1-C4-烷基或五-或六员杂芳基-C1-C4-烷基: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。
Z优选代表氢,C1-C6-烷基,代表各自任选被下列基团一-至三取代的苯基或苯基-C1-C4-烷基: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。
R1优选代表氢,代表各自任选氟和/或氯取代的C1-C10-烷基,C3-C10-烯基,C3-C6-炔基,代表各自任选氟-,氯-,C1-C4-烷基-,C1-C4-烷氧基取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C5-C8-环烯基,或代表各自任选被下列基团一-至四取代的苯基,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: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。
R2优选代表氢,C1-C6-烷基或C3-C6-烯基。
R1,R2还与它们连接的氮原子一起优选代表各自任选C1-C4-烷基取代的五-至八员环,其中任选一个亚甲基可被氧或硫替换。
R3优选代表各自任选氟和/或氯取代的C1-C10-烷基,C2-C10-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,各自任选氟,氯,C1-C4-烷基和/或C1-C4-烷氧基取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C3-C8-环烷氧基,代表各自任选被下列基团一-至四取代的苯基,苯氧基,苄氧基,五-或六员杂芳基或苯基-C1-C4-烷基: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,或在为Ar中所列的基团a),c)和f)的情况下,还代表基团
R4优选代表氢或C1-C4-烷基。
R5优选代表氢或任选氟-和/或氯取代的C1-C4-烷基。
R6优选代表氢,各自任选氟-和/或氯取代的C1-C10-烷基,C3-C8-烯基,C3-C8-炔基,C1-C10-烷氧基,C3-C8-烯氧基,任选氟-,氯-,C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基,其中任选一个亚甲基可被氧或硫替换,代表各自任选被下列基团一-至四取代的苯基,苯基-C1-C4-烷基或苯基-C1-C2-烷氧基: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。
R7优选代表氢,C1-C6-烷基或C3-C6-烯基。
R6,R7还与它们连接的氮原子一起优选代表任选C1-C4-烷基取代的五-至八员环,其中任选一个亚甲基可被氧或硫替换。
式(I)‘化合物中,下列化合物是合适的:
K特别优选代表氧或硫。
Ar特别优选代表Ar1,其中Ar1代表各自任选被下列基团一至三取代的苯基,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:氟,氯,溴,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-烷氧基,C3-C6-烯氧基,C3-C6-炔氧基,C1-C6-烷硫基,C1-C4-烷基磺酰基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,C2-C4-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C2-烷硫基,卤代-C1-C2-烷基磺酰基,羟基,巯基,硝基,氰基,氨基或下列基团之一
a)-O-COR3,
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1: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-,吡啶氧基,嘧啶氧基,噻唑氧基,吡啶基-S(O)g-,嘧啶基-S(O)g-或噻唑基-S(O)g-,其中就其本身来说这些取代基任选被下列基团一-至三取代:氟,氯,溴,C1-C4-烷基,C2-C4-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,其中g代表0,1或2。
Y特别优选代表氢,C1-C10-烷基,C1-C6-卤代烷基,C3-C8-烯基,C1-C4-烷氧基-C2-C3-烷基,C1-C4-烷硫基-C2-C3-烷基,代表任选C1-C4-烷基-,C1-C4-烷氧基-,C1-C2-卤代烷基-,氟-或氯-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C2-烷基,代表各自任选被下列基团一-至三取代的苯基-C1-C2-烷基,噻唑基甲基或吡啶基甲基: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。
Z特别优选代表氢,C1-C3-烷基,代表各自任选被下列基团一-或二取代的苯基或苄基: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。
R1特别优选代表氢,代表各自任选氟和/或氯取代的C1-C6-烷基,C2-C6-烯基,C3-C4-炔基,代表任选氟-,氯-,C1-C2-烷基-,C1-C2-烷氧基取代的C3-C6-环烷基或代表各自任选被下列基团一或二取代的苯基或苄基: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。
R1特别优选代表氢,代表各自任选氟和/或氯取代的C1-C4-烷基或C3-C4-烯基。
R1,R2还与它们连接的氮原子一起特别优选代表任选甲基取代的五或六员环,其中任选一个亚甲基可被氧替换。
R3特别优选代表各自任选氟和/或氯取代的C1-C6-烷基,C2-C6-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,各自任选氟-,氯-,C1-C2-烷基-和/或C1-C2-烷氧基取代的C3-C6-环烷基或C3-C6-环烷氧基,其中任选一个亚甲基可被氧替换,代表各自任选被下列基团一或二取代的苯基,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: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,或在为Ar中所列的基团a),c)和f)的情况下,还代表基团
R4特别优选代表氢。
R5特别优选代表氢,甲基和乙基。
R6特别优选代表氢,各自任选氟和/或氯取代的C1-C6-烷基,C3-C6-烯基,C3-C6-炔基,C1-C6-烷氧基,C3-C6-环烷基,其中任选一个亚甲基可被氧替换,代表各自任选被下列基团一或二取代的苯基或苯基-C1-C2-烷基: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。
R7特别优选代表氢或C1-C4-烷基。
R6,R7还与它们连接的氮原子一起特别优选代表任选C1-C2-烷基取代的五或六员环,其中任选一个亚甲基可被氧替换。
式(I)‘化合物中,下列化合物是适合的:
K更特别优选代表氧或硫。
Ar更特别优选代表Ar1,其中Ar1代表任选被下列基团一-至三取代的苯基:氟,氯,溴,甲基,乙基,丙基,异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,丙氧基,异丙氧基,仲-,正-,异-或叔丁氧基,烯丙氧基,甲代烯丙氧基,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,亚甲二氧基,二氟亚甲二氧基,四氟亚乙二氧基,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,氰基或氨基,或代表任选被下列基团一-或二取代的吡啶基:氟,氯,溴,甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,甲硫基,乙硫基或三氟甲基,
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,吡啶基,噻吩基,四唑基,三唑基或苯氧基,其中就其本身来说这些取代基还任选被下列基团一-或二取代:氟,氯,溴,甲基,乙基,正-或异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,异丙氧基,仲-,正-或叔丁氧基,三氟甲基,三氟甲氧基,硝基或氰基。
X更特别优选代表-CN,-CO-NH2,
Y更特别优选代表氢,C1-C6-烷基,C1-C4-卤代烷基,烯丙基,3-丁烯基,C1-C4-烷氧基-C2-烷基,代表各自任选甲基-,甲氧基-,三氟甲基-,氟-或氯-取代的环丙基,环戊基,环己基,环丙基甲基,环戊基甲基,环己基甲基或代表任选下列基团一或二取代的苄基:氟,氯,溴,甲氧基,甲基,三氟甲基,三氟甲氧基,氰基或硝基或代表任选氯取代的吡啶基甲基或三唑基甲基。
Z更特别优选代表氢,甲基,乙基,代表各自任选被下列基团一或二取代的苯基或苄基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基。
R3更特别优选代表甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,乙烯基,三氟甲基,甲氧基,乙氧基,丙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,环丙基,环戊基,环己基,环戊氧基,环己氧基,代表各自任选被下列基团一-或二取代的苯基,吡啶基或苄基:氟,氯,溴,甲基,正-,仲-,异-或叔丁基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基,或为Ar中所列的基团a),c)和f)的情况下,还代表基团
R5更特别优选代表氢或甲基。
R6更特别优选代表氢,甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,环丙基,环戊基,环己基,代表任选被下列基团一-或二取代的苯基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基。
R7更特别优选代表氢,甲基或乙基。
R6,R7与它们连接的氮原子一起更特别优选代表吡咯烷基,哌啶基或吗啉基。
式(I)‘化合物中,下列化合物是适合的:
K尤其优选代表氧。
Ar尤其优选代表Ar1,其中Ar1代表任选被下列基团一-至三取代的苯基:氟,氯,溴,甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,甲氧基,乙氧基,丙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,烯丙氧基,甲代烯丙氧基,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,亚甲二氧基,二氟亚甲二氧基,四氟亚乙二氧基,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,氰基或氨基,或代表任选被下列基团一-或二取代的吡啶基:氟,氯,溴,甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基或三氟甲基,
或代表Ar2,其中Ar2代表另外通过苯基或苯氧基取代的Ar1,其中就其本身来说这些取代基任选被下列基团一-或二取代:氟,氯,溴,甲基,乙基,异丙基,正-,仲-,异或叔丁基,甲氧基,乙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,三氟甲基,三氟甲氧基,硝基或氰基。
X尤其优选代表CN。
Y尤其优选代表氢,C1-C6-烷基,C1-C3-卤代烷基,环丙基,环戊基,环己基,环丙基甲基,环戊基甲基或环己基甲基。
Z尤其优选代表氢或甲基。
所有上述式(I)化合物既可以以顺式也可以以反式异构体存在。为简便说明,在化合物的通式中各自仅给出一种异构体。然而,各自其它异构体也包括在本发明中。
上述一般或优选基团定义既适用于式(I)终产物,也相应地适用于各自制备所需的起始物和中间体。这些基团定义可任意互相组合,即包括上述所给优选范围之间的组合。
本发明优选其中包括由作为上述优选定义组合的那些式(I)化合物。
本发明特别优选其中包括由作为上述特别优选定义组合的那些式(I)化合物。
本发明更特别优选其中包括由作为上述更特别优选定义组合的那些式(I)化合物。
本发明尤其优选其中包括由作为上述尤其优选定义组合的那些式(I)化合物。
饱和或不饱和的烃基,如烷基或烯基,如可能各自可为直链或支链,也包括与杂原子结合,如烷氧基。
除非另有说明,任选取代的基团是一或多取代的,其中在多取代的情况下,取代基可以相同或不同。
已发现新的式(I)化合物可通过下述方法制备:
Ar,X,Y和Z如上定义和
K代表氧,
它的制备方法即
Ar和X如上定义,
与式(III)化合物反应其中
Y和Z如上定义但不代表氢和
W代表O或S(O)g,其中g代表0或2,和
R8代表烷基,特别是C1-C6-烷基,或苄基,
如适合在存在稀释剂和如适合在存在碱或酸和/或式(IV)的金属化合物的条件下进行上述反应
Me(V)2 (IV)其中
Me代表二价过渡金属原子,特别是镍,和
V代表螯合配位体,特别是二齿螯合配位体,如,例如乙酰丙酮酸根(Acetylacetonate)(R.G.Glushkov et a1.,Khim.-Farm.Zh.
24,(7),(1990),24-27;M.V.Mezent seva et al.,Khim.-Farm.Zh.
25,(12),(1991),19-23;G.Dannhardt,A.Bauer,Pharmazie
51,(1996),805-810)。
Ar,X,Y和Z如上定义
和
K代表氧,
Ar和X如上定义,
和
Hal代表卤素,特别是氯或溴,
与式(VI)化合物反应其中
Y和Z如上定义,但不代表氢,
Ar,X,Y和Z如上定义
如适合在存在碱和如适合在存在三价磷化合物(例如三苯基膦,亚磷酸三乙酯)的条件下,进一步反应,消除硫和卤化氢获得式(I)化合物
其中
Ar,X,Y和Z如上定义
(参见A.Eschenmoser et al.,Helv.Chim.Acta
54,(1971),710-734;V.Issartel et al.,C.R.Acad.Sci.,Ser.II,Mec.,Phys.,Chim.,Astron.
321,(12),(1995),521-524)。
Ar,X,Y和Z如上定义和K代表氧,
Ar和X如上定义,
与式(VIII)化合物缩合其中
Z如上定义和
R9代表C1-C4-烷基,优选甲基和乙基,以及将所得中间体,优选不进行中间体分离,与式(IX)的胺反应
Y-NH2 (IX)其中
Y如上定义,
如适合在存在稀释剂和如适合在存在碱的条件下进行反应。
(D)还发现式(I)化合物其中
Ar,X,Y和Z如上定义和
K代表硫,
可通过下述方法,即将式(I)化合物其中
Ar,X,Y和Z如上定义和
K代表氧,
在存在硫化试剂如,例如五硫化二磷或2,4-双(4-甲氧基苯基)-1,2,3,4-二硫杂磷杂环丁烷(dithiaphosphetan)2,4-硫化物(Lawesson试剂)存在溶剂的条件下反应制备。
Ar,X,Y和Z如上定义,
Ar具有上面Ar2中所述定义和
K代表氧,
可通过下述方法获得,即在存在溶剂,如适合在存在碱和贵金属络合物,优选钯络合物的条件下
Ar1,X,Y和Z如上定义
和
Hal代表卤素,特别是溴,
与式(X)的硼酸反应
Ar2’-B(OH)2 (X),其中
Ar2’代表上面Ar2下作为对Ar1的另外的取代基所列的取代基。
根据方法B,使用例如2-溴-2-(3-氯苯甲酰基)乙腈和N-甲硫代苯甲酰胺作为起始物,反应过程可由下述反应路线表示:
根据方法C,使用例如3,4-二氯-苯甲酰基-乙腈,原乙酸甲酯和异丙胺作为起始物,反应过程可由下述反应路线表示:
根据方法D,使用例如Z-2-(4-三氟甲基-苯甲酰基)-3-(N-乙氨基)丁烯腈和Lawesson试剂作为起始物,反应过程可由下述反应路线表示:
根据方法E,使用例如2-(4-溴-苯甲酰基)-3-(N-甲氨基)丁烯腈和4-氯-苯基硼酸作为起始物,反应过程可由下述反应路线表示:
Ar,X如上定义,
是已知的或可由文献中原则上已知的方法制备(Organikum,16threvised edition,pp.415,417,VEB Deutscher Verlag derWissenschaften,Berlin 1986,德国专利申请,申请号为19851986和10007286和WO00/27812)。
式(II)化合物的制备方法是例如存在酸(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)和如适合在存在稀释剂(例如含水醇类,如甲醇或乙醇),温度在0℃-200℃,优选20℃-150℃条件下,水解式(XI)化合物其中
Ar如上定义,
R10代表可任选取代的烷基,特别是C1-C6-烷基,或苄基,
然后进行脱羧反应,其中基团的消除还任选通过已知方法(Bowman,Fordham,J.Chem.Soc.1951,2758),使用分子氢,在压力为1-100巴,如适合在存在溶剂,如,例如甲醇,乙醇或乙酸乙酯,温度在-20至100℃,优选室温下,以及在存在过渡金属,如,例如任选固定在载体,如,例如活性炭或硫酸钡上的钯,镍,铑或铂的条件下水解进行。
式(XI)化合物可通过已知方法制备(Organikum,16th revisededition,p.480,VEB Deutscher Verlag der Wissenschaften Berlin1986)。
式(XI)化合物的制备是,例如存在碱(例如金属醇盐,如甲醇钠或乙醇钠)以及如适合在存在稀释剂(例如醚或由醇盐衍生的醇),在温度为0℃-150℃,优选20-120℃的条件下,通过将式(XII)化合物其中
Ar如上定义,
与式(XIII)的氰基乙酸酯反应而制得其中
R10代表烷基,特别是C1-C6-烷基,或苄基。
某些式(XII)化合物是新的,而且通常它们可由原则上已知方法制备(例如Organikum,16th revised edition,p.423,VEB DeutscherVerlag der Wissenschaften,Berlin 1986)。
式(XII)化合物的制备是,例如如适合在存在稀释剂(例如任选氯化脂族或芳族烃,如甲苯或二氯甲烷),温度为0℃-150℃,优选20℃-100℃的条件下,将式(XIV)化合物其中
Ar如上定义,
与卤化剂(例如亚硫酰氯,光气,三氯化磷)反应制得。
式(XIII)的氰基乙酸酯是已知的有机化合物。
通式(XIV-b)中的某些化合物是已知的,或它们可通过已知方法合成其中
B1代表氢或氟和
B8代表氢,羟基,代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选卤素取代的烯基或炔基,代表各自任选卤素或烷基取代的环烷基或环烷基烷基,代表各自任选卤素取代的烷氧基或烯氧基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基或芳烷氧基。
此处,B8优选代表氢,羟基,代表各自任选氰基-,卤素-,C1-C4-烷氧基-,C1-C4-烷基羰基-或C1-C4-烷氧基羰基取代的C1-C8-烷基,C1-C8-烷基羰基,C1-C8-烷氧基羰基,C1-C8-烷硫基或C1-C8-烷基磺酰基,代表各自任选卤素取代的C2-C6-烯基或C2-C6-炔基,代表各自任选卤素-或C1-C4-烷基取代的C3-C8-环烷基或C3-C8-环烷基-C1-C4-烷基,代表各自任选卤素取代的C1-C8-烷氧基或C2-C8-烯氧基,代表各自任选氰基-,卤素-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-或C1-C4-卤代烷氧基取代的苯基-C1-C4-烷基或苯基-C1-C4-烷氧基。
该新化合物的制备,尤其可通过本身已知方法,在存在有机金属化合物条件下,使用CO2将通式(XV)化合物转化成通式(XIV-b)化合物(例如Organikum,16th revised edition,p.499,VEB Deutscher Verlagder Wissenschaften 1986)其中
B1代表氢或氟和
B8如上定义。
除了有机镁化合物外,适于用作有机金属碱的化合物还包括有机锂化合物,它们是有机化学中的已知合成化合物。适合的溶剂/稀释剂是烃(如甲苯)或醚(如,例如四氢呋喃或乙醚)。还可以使用上述溶剂的混合物。
反应温度通常为-100℃至80℃,优选-80℃至25℃(室温)。为进行处理,将反应混合物用水或可以是稀的或浓的无机酸,如盐酸稀释,使用水不混溶的溶剂分离产物并通过常规方法,例如通过结晶纯化产物。
某些通式(XV)化合物,其中
B1代表氢或氟和
B8如上定义,
是新的,而且它们可通过已知方法合成(Sicker etal.,Tetrahedron,
31,(1996),10389;Bell et al.,J.Med.Chem.,33,(1990),380)。
新的式(XV)化合物,其中
B1代表氢或氟和
B8代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选卤素取代的烯基或炔基,代表各自任选卤素-或烷基取代的环烷基或环烷基烷基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基,
其中B1代表氢或氟和B9代表氢,
与式(XVI)的烷基化剂反应制备
B8-X1 (XVI),其中
B8代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选卤素取代的烯基或炔基,代表各自任选卤素-或烷基取代的环烷基或环烷基烷基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基和
X1代表卤素,特别是碘,溴或氯,或其它离去基团,例如活化酯,如甲磺酸酯或甲苯磺酸酯,或
如适合在存在碱和存在溶剂的条件下由通式(XV)’化合物,其中B1代表氢或氟和B9代表羟基,与式(XVII)’的烷基化剂反应制备
B10-X1 (XVII)’,其中
B10代表各自任选卤素-取代的烷基或烯基或代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基和
X1代表卤素,特别是碘,溴或氯,或其它离去基团,例如活化酯,如甲磺酸酯或甲苯磺酸酯。
除了碱金属氧化物和碱土金属氧化物外,适用于反应中的碱是叔胺,如三乙胺,吡啶或N,N-二乙基苯胺,它们可以摩尔比例但也可以以过量使用。
除了烃如甲苯外,适合的溶剂或稀释剂还包括卤代烃,如二氯甲烷。可以使用极性非质子溶剂/稀释剂,如二甲基甲酰胺,还包括上述溶剂的混合物。反应温度通常在反应混合物的熔点至沸点之间,优选-10℃至80℃。
文献中已公开了通式(XV)’化合物,其中B1代表氢或氟和B9代表氢(Huang et al.,Synthesis(1984),851;JP63132881)并且可根据本身已知方法通过氧化反应转化成通式(XV)’化合物,其中B1代表氢或氟以及B9代表羟基(P.G.Sammes et al.,J.Chem.Soc.,Perkin TransI,(1979),2481)。
而且,通式(XIV-b)化合物,其中
B1代表氢或氟和
B8如上定义,
是通过水解式(XVIII)化合物获得其中
B1代表氢或氟,
B8如上定义和
B11代表烷基或苄基,特别是C1-C6-烷基或苄基,可任选被基团R1或R2全部或部分取代,
该水解反应是在存在酸(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)和如适合在存在稀释剂(例如含水醇,如甲醇或乙醇),温度为0℃至200℃,优选20℃至150℃的条件下进行。还任选在压力为1至100巴,如适合存在溶剂,例如甲醇,乙醇或乙酸乙酯,温度为-10℃至100℃,优选室温,存在过渡金属,例如任选固定在载体,如活性炭或硫酸钡上的钯,镍,铑或铂的条件下,采用已知方法(Bowman,Fordham J.Chem.Soc.,1951,2758)使用分子氢氢解消去基团B11。
另外,通式(XVIII)化合物,其中
B1代表氢或氟和
B8如上定义和
B11代表氢,烷基或苄基,特别是C1-C6-烷基或苄基,可任选各自被基团R1或R2全部或部分取代,
可根据本身已知常规方法,通过将通式(XV)化合物,其中
B1代表氢或氟和
B8如上定义,
B11代表氢,烷基或苄基,特别是C1-C6-烷基或苄基,可任选各自被基团R1或R2全部或部分取代,
反应在存在CO,压力为1巴至100巴,优选1巴至50巴以及温度在20℃至300℃,优选20℃至150℃,存在催化剂,例如钯盐或钴盐或过渡金属羰基化合物,如,例如Co2(CO)8,如适合存在配位体(如,例如,三苯基膦,(3-磺酰(sulfo)苯基)膦三钠盐),存在碱(例如碱金属氢氧化物,如氢氧化钠或氢氧化钾,或有机碱,如三乙胺或吡啶)以及稀释剂(例如醇,水,四氢呋喃,二氯甲烷,甲苯或上述稀释剂的混合物)的条件下进行。任选反应还存在相转移催化剂(例如乙二醇,冠醚或铵盐,如溴化四丁铵或氯化四丁铵)或辅助剂(例如沸石)或在光照条件下,根据已知方法进行(Ziolkowski et al.,J.Mol.Catal.A:Chem.,
154,(2000),93;P.Kalck et al.,J.Organomet.Chem.,
482,(1994),45;Du Pontde Nemours & Co US 2734912;Alper,H.et al.,Angew.Chem.,96,(1984),710;Takatori K.et al.,Tet rahedron,
54,(1998),15861)。
B1代表氢或氟和
B8代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选卤素取代的烯基或炔基,代表各自任选卤素-或烷基取代的环烷基或环烷基烷基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基,
如适合在存在碱和存在溶剂的条件下由通式(XIV-b)化合物
其中
B1代表氢或氟和
B8代表氢,
与式(XVII)’的烷基化剂反应获得
B10-X1 (XVII)’其中
B10代表各自任选卤素取代的烷基或烯基或代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基和
X1代表卤素,特别是碘,溴或氯,或其它离去基团,例如活化酯,如甲磺酸酯或甲苯磺酸酯。
除了碱金属氧化物和碱土金属氧化物外,适用于反应中的碱是叔胺,如三乙胺,吡啶或N,N-二乙基苯胺,它们可以摩尔比例但也可以以过量使用。除了烃如甲苯外,适合的溶剂或稀释剂还包括卤代烃,如二氯甲烷。可以使用极性非质子溶剂/稀释剂,如二甲基甲酰胺,还包括上述溶剂的混合物。反应温度通常在反应混合物的熔点至沸点之间,优选-10℃至80℃。
W,Y,Z和R8如上定义,
它们可根据已知方法制备(参见实施例III-a-1和H.Bredereck,F.Effenberger,E.Henseleit,Chem.Ber.1965,
98,2754;P.Deslongchamps,O.C.Ukken,A.Guida,R.J.Taillefer,Nouv.J.Chim.1977,
235,240;R.M.Moriarty,C.L.Yeh,K.C.Ramey,P.W.Whiteburst,J.Am.Chem.Soc.1970,
21,6360)。
Ar和Hal如上定义和X代表氰基,
或们可根据已知方法制备(Gakhar H.K.et al,J.IndianChem.Soc.
43(1971)953;Corsaro A.Heterocycles
23(1985)2645)。
Z和Y如上定义,
原则上是有机化学领域的已知化合物,并且某些化合物是市售产品(还可参见制备实施例5)。
Z和R9如上定义,
原则上是有机化学领域的已知化合物,并且它们中的某些化合物是市售产品。
大多数式(IX)化合物是市场上可以买到的化合物或者它们可根据有机化学领域的通常已知方法制备。
用于方法E的某些式(X)的芳基硼酸是市售产品,或它们可以根据已知方法制备。
适用于方法(A)的稀释剂是所有对反应物具有惰性的有机溶剂。优选使用任选氯化的脂族或芳族烃,如甲苯,二甲苯,均三甲苯,氯苯,氯仿,二氯甲烷,还有极性溶剂,如二甲基亚砜,环丁砜,二甲基甲酰胺,二甲基乙酰胺或N-甲基吡咯烷酮。还可以使用醚,如乙醚,四氢呋喃或二噁烷。
适用于方法(A)的碱是所有常用的并不水解反应物的酸性接受体。
优选使用叔胺,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)和N,N-二甲基苯胺。
适用于方法(A)的酸是所有并不水解反应物的酸。优选使用有机酸,如对甲苯磺酸和三氟乙酸。
当进行方法(A)时,反应温度可在较宽的范围内变化。该方法在-20℃至160℃下进行是有利的,优选0℃至120℃。
方法(A)优选在大气压下进行。
当进行方法(A)时,以式(II)反应组分计式(III)反应物是以等摩尔量或较大过量(至多5摩尔),优选1.5至2倍摩尔量使用。
任选使用的碱优选使用与式(II)反应组分等摩尔量。如适合,优选使用催化量的酸。
方法(B)的特征在于如适合在存在稀释剂和如适合在存在酸结合剂的条件下将式(V)化合物各自与式(VI)的硫代酰胺反应。
可根据已知方法制备式(V)起始物(Gakhar H.K.et al.,J.IndianChem.Soc.
43,(1971),953或Corsaro A.,Heterocycles23,(1985),2645)。式(VI)化合物可由相应的酮化合物使用亚硫酰化剂,特别是Lawesson试剂,在惰性溶剂,如,例如甲苯中制备获得(参见制备实施例5)。
根据本发明适用于方法(B)的稀释剂是所有对式(V)化合物惰性的溶剂。优选使用烃,如汽油,苯,甲苯,二甲苯和四氢化萘(Tetralin),还包括卤代烃,如二氯甲烷,氯仿,四氯化碳,氯苯和邻二氯苯,此外酮,如丙酮和甲基异丙基酮,还有醚,如乙醚,四氢呋喃和二噁烷,其它还有羧酸酯,如乙酸乙酯,以及强极性溶剂,如二甲基甲酰胺,N-甲基吡咯烷酮,二甲基亚砜和环丁砜。
根据本发明适用于方法(B)反应的酸结合剂是所有常用酸性接受体。优选使用叔胺,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,聚合物碱,如二异丙基氨基聚苯乙烯,还包括碱土金属氧化物,如氧化镁和氧化钙,另外碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠,碳酸钾和碳酸钙,以及碱金属氢氧化物,如氢氧化钠和氢氧化钾。
根据本发明适用于方法(B)的磷试剂是亚磷酸烷基酯,如亚磷酸三乙酯,亚磷酸三丁酯,或三苯基膦类,如三苯基膦。
根据本发明方法(B)的反应温度可在较宽的范围内变化。通常,该方法是在0℃至200℃进行,优选+20℃至150℃。
根据本发明进行方法(B)时,式(V)起始物和式(VI)的硫代酰胺通常各自使用近似等摩尔量。然而,还可以一种或另一种组分较大过量使用。处理是通过常规方法进行。
方法(C)的特征在于首先将式(II)化合物与式(VIII)的原酸酯缩合,然后将所得缩合物,没有中间步骤,直接与式(IX)的胺反应。
根据本发明适用于方法(C)反应的酸结合剂,如适合,包括所有常用酸接受体。优选使用叔胺,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,聚合物碱,如二异丙基氨基聚苯乙烯,还包括碱土金属氧化物,如氧化镁和氧化钙,另外碱金属碳酸盐和碱土金属碳酸盐,如碳酸钠,碳酸钾和碳酸钙,以及碱金属氢氧化物,如氢氧化钠和氢氧化钾。
根据本发明适用于方法(C)的稀释剂是所有对原酸酯惰性的溶剂。优选使用烃,如汽油,苯,甲苯,二甲苯和四氢化萘,还包括卤代烃,如二氯甲烷,氯仿,四氯化碳,氯苯和邻二氯苯,此外酮,如丙酮和甲基异丙基酮,还有醚,如乙醚,四氢呋喃和二噁烷,其它还有羧酸酯,如乙酸乙酯,另外腈如乙腈,以及强极性溶剂,如二甲基甲酰胺,二甲基乙酰胺,N-甲基吡咯烷酮,二甲基亚砜和环丁砜。根据另一变化方法,原酸酯本身还可以用作溶剂。该变化方法是特别优选的。
根据本发明方法(C)的反应温度可在较宽的范围内变化。通常,该方法是在-20℃至200℃之间进行,优选0℃至150℃。
根据本发明方法(C)通常是在大气压下进行的。
根据本发明进行方法(C)时,式(II)起始物和式(IX)的适合的胺通常各自使用近似等摩尔量。然而,还可以以一种或另一种组分较大过量使用(至多10摩尔,优选至多3摩尔)。通常式(VIII)的原酸酯以较大过量使用。处理是根据常规方法进行的,即抽除稀释剂和过量反应物以浓缩反应混合物并进一步纯化剩余物。
方法(D)的特征在于如适合存在稀释剂的条件下将式(I)化合物,其中Ar,X,Y和Z如上定义和K代表氧,与硫化剂反应。
使用的硫化剂是用于合成的已知化合物,如,例如,五硫化二磷或2,4-双(4-甲氧基苯基)-1,2,3,4-二硫杂磷杂环丁烷2,4-硫化物(Lawesson试剂)。
根据本发明适用于方法(D)的稀释剂是所有对上述试剂具有惰性的溶剂。优选使用烃,如汽油,苯,甲苯,二甲苯和四氢化萘,还包括卤代烃,如二氯甲烷,氯仿,氯苯和邻二氯苯,醚,如四氢呋喃,二噁烷,二异丙醚或甲基叔丁基醚。
根据本发明方法(D)的反应温度可在较宽的范围内变化。
通常,该方法是在0℃至250℃之间进行,优选40℃至200℃。
根据本发明当进行方法(D)时,式(I)起始物和上述试剂通常各自使用近似等摩尔量。然而,上述试剂还可以使用较大过量至多5摩尔。处理是通过常规方法进行的。
用于方法(E)的某些芳基硼酸,如,例如,4-氯-苯基硼酸是市场上可以买到的,或者它们可由已知方法制备。
根据本发明适用于方法(E)的酸接受体是无机或有机碱。它们优选包括碱土金属氢氧化物,乙酸盐,碳酸盐或碳酸氢盐或碱金属氢氧化物,乙酸盐,碳酸盐或碳酸氢盐,如,例如氢氧化钠,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,如,例如,氟化铯,以及叔胺,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),二氮杂二环壬烯(DBN)。
根据本发明适用于方法(E)的稀释剂是水,有机溶剂和它们的任意混合物。可以提及的实例包括:脂族,脂环族或芳族烃,如,例如,石油醚,己烷,庚烷,环己烷,甲基环己烷,苯,甲苯,二甲苯或萘烷;卤代烃,如,例如,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,如乙醚,二异丙醚,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,二乙二醇二甲醚或茴香醚;醇,如甲醇,乙醇,正或异丙醇,正-,异-,仲或叔丁醇,乙二醇,1,2-丙二醇,乙氧基乙醇,甲氧基乙醇,二乙二醇单甲醚,二乙二醇单乙醚;水。
根据本发明方法(E)的反应温度可在较宽的范围内变化。通常,该方法是在0℃至+200℃之间进行的,优选50℃至+150℃。
根据本发明当进行方法(E)时,式(X)的硼酸,其中Ar2’如上定义和式(I1)化合物,其中Ar1,K,X,Y,Z和Hal如上定义,两者之间的摩尔比例是1∶1至3∶1,优选1∶1至2∶1。通常每摩尔式(I1)化合物,使用0.005-0.5摩尔,优选0.01-0.1摩尔的催化剂。通常使用过量的碱。
本发明活性化合物特别适合用作脱叶剂,干燥剂,除草秆剂,和尤其是除草剂。从最广义上讲,杂草应理解为生长在不适合场所的所有植物。本发明物质是否用作灭生性或选择性除草剂基本上是根据其使用量而确定的。
本发明活性化合物用于防治杂草时的所需剂量为0.001-10kg/ha,优选0.005-5kg/ha。
本发明活性化合物例如可用于下述植物:
双子叶杂草属:苘麻属,苋属,豚草属,单花葵属,春黄菊属,Aphanes,滨藜属,雏菊属,鬼针草属,荠菜属,飞廉属,决明属,矢车菊属,藜属,蓟属,旋花属,曼陀罗属,金钱草,刺酸模属,糖芥属,大戟属,鼬瓣花属,牛膝菊属,猪殃殃属,木槿属,番薯属,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,车前属,蓼属,马齿苋属,毛茛属,萝卜属,薄菜属,水松叶属,酸模属,猪毛菜属,千里光属,田菁属,黄花稔属,欧白芥属,茄属,苦苣菜属,尖瓣花属,繁缕属,蒲公英属,遏蓝菜属,车轴草属,荨麻属,婆婆纳属,堇菜属,苍耳属。
双子叶作物属: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,番茄属,烟草属,菜豆属,豌豆属,茄属,巢菜属。
单子叶杂草属:山羊草属,冰草属,翦股颍属,看麦娘属,假翦股颍属,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,荸荠属,蟋蟀草属,画眉草属,野黍属,羊茅属,飘拂草属,异蕊花属,白茅属,鸭嘴草属,千金子属,毒麦属,雨久花属,黍属,雀稗属,草属,梯牧草属,早熟禾属,筒轴茅属,慈菇属,草属,狗尾草属,高粱属。
单子叶作物属:葱属,菠萝,天门冬属,燕麦属,大麦属,稻属,黍属,甘蔗属,黑麦属,高粱属,黑小麦,小麦,玉米属。
根据本发明,可以处理所有植物和植物各部分。此处植物可以理解为所有植物和植物群落,如需要和不需要的野生植物或作物(包括自然长出的作物)。作物可以是通过常规育种和优化方法或通过生物技术和遗传工程方法或上述方法的结合获得的植物,包括转基因植物和包括获得或没有获得植物育种者证书(Sortenschutzrechte)保护的植物栽培品种。植物的各部分可理解为所有地上和地下部分以及植物组织,如茎、叶、花和根,可提及的实例为叶片、针叶、枝条、树干、花、子实体、果实和种子以及根、块茎和根状茎。植物各部分还包括收获的植物和植物营养体以及有性繁殖材料,例如种苗、块茎、根状茎、插条和种子。
使用活性化合物按照本发明进行植物和植物各部分的处理是通过常规处理方法直接施用或作用于它们的环境、生境或贮藏区进行处理,例如浸渍、喷雾、熏蒸、弥雾、撒播、刷涂以及在繁殖材料,特别是种子的情况下还可以进行一层或多层包衣。
但是,本发明活性化合物的应用丝毫不限制于上述属,还可以相同的作用方式扩展到其它植物。就本发明活性化合物的应用来说,特别优选用于转基因植物,因为在这种情况下可以观察到协同增效活性增强。
根据其浓度,所述活性化合物适合于灭生性地防治杂草,例如在工业区和铁轨,种树或没种树的路或广场。同样,所述化合物还可用来防治多年生栽培作物,例如为森林,观赏树木,果园,葡萄园,柑桔园,坚果园,香蕉园,咖啡园,茶园,橡胶园,油棕园,可可园,浆果种植园和啤酒花栽培区,草皮,草坪和牧草地,并可选择性地在一年生栽培作物中防治杂草,。
本发明活性化合物非常适合于通过苗前和苗后处理方法选择性地防除双子叶作物中的单子叶杂草。例如它们可非常有效地防除棉花或糖甜菜中的有害的杂草。
所述活性化合物可被转化成为常规的制剂,如液剂,乳剂,可湿性粉剂,悬浮剂,粉剂,细粉剂,糊剂,可溶粉剂,颗粒剂,浓悬浮乳剂,用活性化合物浸渍的天然和合成材料和在聚合物中的微胶囊。
这些制剂是以已知方法生产的,例如,通过将活性化合物与填充剂,即液体溶剂和/或固体载体混合而生产,如适合可使用表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
在使用水作为填充剂的情况下,例如,也可使用有机溶剂作为助溶剂。适当的液体溶剂主要有:芳香烃类,如二甲苯,甲苯或烷基萘,氯代芳烃类和氯代脂肪烃类,如氯苯,二氯乙烷或二氯甲烷,脂肪烃类,如环己烷或链烷烃,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇及其醚和酯类,酮类,如丙酮,甲基乙基酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适当的固体载体有:
例如,铵盐和天然矿物粉末,如高岭土,粘土,滑石,白垩,石英,硅镁土,蒙脱土或硅藻土,和合成矿物粉末,如高分散二氧化硅,氧化铝和硅酸盐;适合用于颗粒剂的固体载体有:例如,粉碎和分级的天然岩石,如方解石,大理石,浮石,海泡石和白云石,以及无机和有机粉末的合成颗粒,和有机材料的颗粒如锯末,坚果壳,玉米穗茎和烟草茎;适当的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如亚硫酸化木素废液和甲基纤维素。
在制剂中还可使用粘着剂,如羧甲基纤维素和粉末、颗粒或胶乳状的天然和合成聚合物,如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它添加剂可以是矿物油和植物油。
可以使用着色剂,如无机颜料,例如氧化铁,氧化钛和普鲁士兰,和有机染料,如茜素染料,偶氮染料和金属酞菁染料,和痕量营养物,如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1%-95%,优选按重量计0.5-90%的活性化合物,和除此之外优选填充剂和/或表面活性剂。
本发明活性化合物可使用其市售制剂以及由这些制剂与其它活性化合物混合制备的应用形式使用,其它活性化合物如杀虫剂,引诱剂,消毒剂,杀螨剂,杀线虫剂,杀真菌剂,生长调节物质或除草剂。杀虫剂包括,例如,磷酸酯,氨基甲酸酯,羧酸酯,氯代烃,苯基脲,特别是由微生物生产的物质。在本发明优选实施方案中,还可将安全剂与本发明化合物混合以提高作物的耐受性。
特别优选的混合组分的实例包括下列化合物:
杀真菌剂:
Aldimorph,氨丙膦酸,氨丙膦酸钾盐,Andoprim,敌菌灵,氧环唑,腈嘧菌酯,
苯霜灵,麦锈灵,苯菌灵,苄烯酸,苄烯酸异丁酯,双丙氨膦,乐杀螨,联苯,联苯三唑醇,灭瘟素,糠菌唑,乙嘧酚磺酸酯,丁硫啶,
石硫合剂,Capsimycin,敌菌丹,克菌丹,多菌灵,萎锈灵,Carvon,灭螨锰,灭瘟唑,苯咪唑菌,地茂散,氯化苦,百菌清,乙菌利,Clozylacon,硫杂灵,霜脲氰,环丙唑醇,嘧菌环胺,酯菌胺,
咪菌威,双氯酚,苄氯三唑醇,Diclofluanid,哒菌酮,氯硝胺,乙霉威,苯醚甲环唑,二甲嘧酚,烯酰吗啉,烯唑醇,烯唑醇-M,敌螨普,二苯胺,吡菌硫,灭菌磷,二氰蒽醌,十二环吗啉,多果定,敌菌酮,
敌瘟磷,氧唑菌,乙环唑,乙嘧酚,土菌灵,
噁唑酮菌,咪菌腈,氯苯嘧啶醇,腈苯唑,呋菌胺,种衣酯,拌种咯,苯锈啶,丁苯吗啉,醋酸三苯锡,羟基三苯锡,福美铁,嘧菌腙,氟啶胺,氟联苯菌,氟氯菌核利,氟喹唑,呋嘧醇,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,三乙膦酸铝,三乙膦酸钠,四氯苯酞,麦穗宁,呋霜灵,呋吡唑灵,灭菌胺,呋菌唑,呋醚唑,拌种胺,
双胍盐,
六氯苯,己唑醇,恶霉灵,
抑霉唑,亚胺唑,双胍辛,双八胍盐,双胍辛醋酸盐,Iodocarb,种菌唑,异稻瘟净,异菌脲,Irumamycin,稻瘟灵,氯苯咪菌酮,
春雷霉素,亚胺菌,含铜杀菌剂如:氢氧化铜,环烷酸铜,王铜,硫酸铜,氧化铜,喹啉铜和波尔多液,
代森锰铜,代森锰锌,代森锰,Meferimzone,嘧菌胺,灭锈胺,甲霜灵,叶菌唑,磺菌威,呋菌胺,代森联,苯吡咯菌,噻菌胺,米多霉素,腈菌唑,甲菌利,
福镁镍,异丙消,氟苯嘧啶醇,
呋酰胺,恶霜灵,Oxamocarb,喹菌酮,氧化萎锈灵,Oxyfenthiin,
多效唑,稻瘟酯,戊菌唑,戊菌隆,氯瘟磷,多马霉素,哌丙灵,多抗霉素,Polyoxorim,烯丙苯噻唑,咪鲜胺,腐霉利,霜霉威,Propanosine-sodium,丙环唑,丙森锌,吡菌磷,啶斑肟,嘧霉胺,咯喹酮,氯吡呋醚,
Quinconazole,五氯硝基苯,
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,四环唑,四氟醚唑,噻菌灵,噻菌腈,溴氟唑菌,甲基硫菌灵,福美双,硫氰苯甲酰胺,甲基立枯磷,甲苯氟磺胺,三唑酮,三唑醇,叶锈特,咪唑嗪,水杨菌胺,三环唑,十三吗啉,氟菌唑,嗪胺灵,灭菌唑,
烯效唑,
有效霉素A,乙烯菌核利,烯霜苄唑,
氰菌胺,代森锌,福美锌,以及
咪草酯(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-β-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,
1-异丙基{2-甲基-1-[[[1-(4-甲基苯基)-乙基]-氨基]-羰基]-丙基}-氨基甲酸酯,
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)-乙酮-O-(苯基甲基)-肟,
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮,
1-[(二碘甲基)-磺酰基]-4-甲基-苯,
1-[[2-(2,4-二氯苯基)-1,3-二氧戊环-2-基]-甲基]-1H-咪唑,
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑,
1-[1-[2-[(2,4-二氯苯基)-甲氧基]-苯基]-乙烯基]-1H-咪唑,
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷醇,
2’,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟-甲基-1,3-噻唑-5-甲酰苯胺,
2,2-二氯-N-[1-(4-氯苯基)-乙基]-1-乙基-3-甲基-环丙烷甲酰胺,
2,6-二氯-5-(甲硫基)-4-嘧啶基-硫氰酸酯,
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺,
2,6-二氯-N-[[4-(三氟甲基)-苯基]-甲基]-苯甲酰胺,
2-(2,3,3-三碘-2-丙烯基)-2H-四唑,
2-[(1-甲基乙基)-磺酰基]-5-(三氯甲基)-1,3,4-噻二唑,
2-[[6-脱氧-4-O-(4-O-甲基-β-D-吡喃葡萄糖基)-D-吡喃葡萄糖基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈,
2-氨基丁烷,
2-溴-2-(溴甲基)-戊二腈,
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-吡啶甲酰胺,
2-氯-N-(2,6-二甲基苯基)-N-(异硫氰酸根合甲基)-乙酰胺,
2-苯基苯酚(OPP),
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮,
3,5-二氯-N-[氰基[(1-甲基-2-丙炔基)-氧基]-甲基]-苯甲酰胺,
3-(1,1-二甲基丙基-1-氧代-1H-茚并-2-腈,
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶,
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺,
4-甲基-四唑并[1,5-a]喹唑啉-5(4H)-酮,
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸烷-2-甲胺,
8-羟基喹啉硫酸盐(8-Hydroxychinolinsulfat),
9H-呫吨-2-[(苯基氨基)-羰基]-9-甲酰肼,
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)-氧基]-2,5-噻吩二甲酸酯,
顺式-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇,
顺式-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-唑烷基)-乙酰胺,
N-(6-甲氧基)-3-吡啶基)-环丙烷甲酰胺,
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺,
N-[3-氯-4,5-双-(2-丙炔氧基)-苯基]-N’-甲氧基-甲亚氨酸酰胺(methanimidamid),
N-甲酰基-N-羟基-DL-丙氨酸钠盐,
[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸O,O-二乙酯,
苯基丙基氨基硫代磷酸O-甲基S-苯基酯,
1,2,3-苯并噻二唑-7-硫代羟酸S-甲酯,
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮,
杀细菌剂:
溴硝丙二醇、双氯酚、三氯甲基吡啶、福美镍、春雷霉素、辛噻酮、呋喃羧酸、土霉素、烯丙苯噻唑、链霉素、叶枯酞、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
阿维菌素、乙酰甲胺磷、啶虫脒、氟丙菊酯、棉铃威、涕灭威、砜灭威、顺式氯氰菊酯、甲体氯氰菊酯、双甲脒、齐墩螨素、AZ60541、艾扎丁、甲基吡恶磷、乙基谷硫磷、谷硫磷、三唑锡,
日本甲虫芽孢杆菌、球形芽孢杆菌、枯草芽孢杆菌、苏云金芽孢杆菌、Baculoviruses、蚕白僵菌、纤细白僵菌、恶虫威、丙硫克百威、杀虫磺、苯螨特、高效氟氯氰菊酯、联苯肼酯、联苯菊酯、Bioethanomethrin、生物氯菊酯、仲丁威、溴硫磷A、合杀成、噻嗪酮、特嘧硫磷、丁酮威、Butylpyridaben
硫线磷、甲萘威、克百威、三硫磷、丁硫克百威、杀螟丹、Chloethocarb、氯氧磷、氟唑虫清、毒虫畏、氟啶脲、氯甲磷、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、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺
溴氰菊酯、甲基内吸磷、内吸磷硫赶式异构体、甲基内吸磷硫赶式异构体、丁醚脲、二嗪磷、敌敌畏、除虫脲、乐果、甲基毒虫畏、苯虫醚、乙拌磷、碘酰丁二辛、苯氧炔螨
Efusilanate、Emamectin、右旋烯炔菊酯、硫丹、虫霉属、S-氰戊聚酯、乙硫苯威、乙硫磷、灭线磷、醚菊酯、特苯恶唑、乙嘧硫磷
苯线磷、喹螨醚、苯丁锡、杀螟硫磷、苯硫威、Fenoxacrim、苯氧威、甲氰菊酯、Fenpyrad、Fenpyrithrin、唑螨酯、氰戊菊酯、氟虫腈、氟啶胺、啶蜱脲、溴氟菊酯、氟环脲、氟氰戊菊酯、氟虫脲、Flutenzine、氟胺氰菊酯、地虫硫磷、丁苯硫磷、噻唑磷、Fubfenprox、呋线威
颗粒体病毒
特丁苯酰肼、六六六、庚烯磷、氟铃脲、噻螨酮、烯虫乙酯
吡虫啉、氯唑磷、异柳磷、恶唑磷、齐墩螨素
高效氯氟氰菊酯、氟丙氧脲
马拉硫磷、灭蚜磷、四聚乙醛、甲胺磷、Metharhiziumanisopliae、Metharhizium flavoviride、杀扑磷、甲硫威、灭多威、甲氧苯酰肼、速灭威、恶虫酮、速灭磷、米尔螨素、久效磷
二溴磷、烯啶虫胺、硝虫噻嗪、双苯氟脲、核多角体病毒
氧乐果、杀线威、亚砜磷
玫烟色拟青霉、对硫磷A、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、乙基嘧啶磷、甲基嘧啶磷、丙溴磷、猛杀威、残杀威、丙硫磷、发硫磷、吡蚜酮、吡唑硫磷、反灭虫菊、除虫菊素、哒螨灵、Pyridathion、嘧螨醚、蚊蝇醚
喹硫磷
Ribavirin
杀抗松、硫线磷、氟硅菊酯、艾克敌105、Sulfotep、硫丙磷
氟胺氰菊酯、虫酰肼、吡螨胺、嘧丙磷、氟苯脲、七氟菊酯、双硫磷、灭虫畏、特丁硫磷、杀虫畏、辛体氯氰菊酯、Thiamethoxam、噻丙腈、Thiatriphos、硫环杀、硫双威、久效威、敌贝特、溴氯氰菊酯、四溴菊酯、苯螨噻、唑蚜威、三唑磷、Thiazuron、氯咪唑、敌百虫、杀铃脲、混杀威
蚜灭多、氟吡唑虫、麦柯特尔
YI 5302
己体氯氰菊酯、zolaprofos
(1R-顺)-[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]-2,2-二甲基环丙烷羧酸酯
(3-苯氧基苯基)-甲基-2,2,3,3-四甲基环丙烷羧酸酯
1-[(2-氯-5-噻唑基)甲基]四氢-3,5-二甲基-N-硝基-1,3,5-三嗪-2(1H)-亚胺
2-(2-氯-6-氟苯基)-4-[4-(1,1-二甲基乙基)苯基]-4,5-二氢-噁唑
2-(乙酰氧基)-3-十二烷基-1,4-萘二酮
2-氯-N-[[[4-(1-苯基乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺
2-氯-N-[[[4-(2,2-二氯-1,1-二氟乙氧基)-苯基]-氨基]-羰基]-苯甲酰胺
3-甲基苯基-丙基氨基甲酸酯
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]硫代]-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EG-2348株系
2-苯甲酰基-1-(1,1-二甲基乙基)-肼基苯甲酸,
2,2-二甲基-3-(2,4-二氯苯基)-2-氧代-1-氧杂螺[4,5]癸-3-烯-4-基丁酸酯
[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-(苯基甲基)-4-哒嗪基]氧基]乙基]-氨基甲酸乙酯
N-(3,4,4-三氟-1-氧代-3-丁烯基)-甘氨酸
N-(4-氯苯基)-3-[4-(二氟甲氧基)苯基]-4,5-二氢-4-苯基-1H-吡唑-1-甲酰胺
N-[(2-氯-5-噻唑基)甲基]-N’-甲基-N”-硝基-胍
N-甲基-N’-(1-甲基-2-丙烯基)-1,2-肼二硫代甲酰胺
N-甲基-N’-2-丙烯基-1,2-肼二硫代甲酰胺
[2-(二丙基氨基)-2-氧代乙基]-乙基氨基硫代磷酸O,O-二乙酯。
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、先甲草胺、酰嘧磺隆、莎稗磷、磺草灵、莠去津、唑啶炔草、四唑嘧磺隆、草除灵(乙酯)、呋草黄、苄嘧磺隆(甲酯)、噻草平、Benzobicyclon、吡草酮、新燕灵(乙酯)、双丙氨膦、甲羧除草醚、双草醚(钠盐)、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、丁氧环酮、丁草敌、苯酮唑、醌肟草、双酰草胺、氟酮唑草(乙酯)、甲氧除草醚、草灭畏、氯草敏、氯嘧磺隆(乙酯)、草枯醚、氯磺隆、绿麦隆、Cinidon(-乙酯)、环庚草醚、醚黄隆、Clefoxydim、烯草酮、炔草酸(炔丙酯)、异恶草松、氯甲酰草胺、二氯吡啶酸、Clopyrasulfuron(-甲酯)、唑嘧磺胺盐、Cumyluron、氰草津、Cybutryne、环草敌、环丙嘧磺隆、噻草酮、氰氟草酯(丁酯)、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)、唑嘧磺胺、乙酰甲草胺(乙酯)、野燕枯、吡氟酰草胺、二氟吡隆、恶唑隆、哌草丹、二甲草胺、异戊乙净、二甲吩草胺、Dimexyflam、敌乐胺、双苯酰草胺、敌草快、氟硫草啶、敌草隆、杀草隆、Epoprodan、扑草灭(EPTC)、戊草丹、乙丁烯氟灵、胺苯磺隆(甲酯)、乙氧呋草黄、Ethoxyfen、乙氧嘧磺隆、乙苯酰草、精恶唑禾草灵(乙酯)、Fentrazamide、麦草氟异丙酯、麦草氟异丙酯-L、麦草氟甲酯、啶嘧磺隆、Florasulam、精吡氟禾草灵(丁酯)、Fluazolate、Flucarbazone、Flufenacet、氟唑啶草、氟烯草酸(戊酯)、丙炔氟草胺、Flumipropyn、唑嘧磺草胺、氟草隆、氟咯草酮、乙羧氟草醚(乙酯)、氟胺草唑、Flupropacil、Flurpyrsulfuron(-甲酯,-钠盐)、芴丁酯、氟啶草酮、氯氟吡氧乙酸(-甲基庚基酯)、氟嘧醇、呋草酮、达草氟(甲酯)、噻唑草酰胺、氟磺胺草醚、草铵膦、草甘膦异丙胺盐、氟硝磺酰胺、氟吡乙禾灵、精氟吡甲禾灵、环嗪酮、咪草酯(甲酯)、Imazamethapyr、咪草啶酸、Imazapic、咪唑烟酸、咪唑喹啉酸、咪唑乙烟酸、咪吡嘧磺隆、Iodosulfuron(-甲酯,钠盐)、碘苯腈、异丙乐灵、异丙隆、异恶隆、异噁草胺、Isoxachlortole、异噁氟草、异恶草醚、乳氟禾草灵、环草啶、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、Mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、溴谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲磺隆(甲酯)、禾草敌、绿谷隆、萘丙胺、敌草胺、草不隆、烟嘧磺隆、氟草敏、坪草丹、氨磺乐灵、炔丙噁唑草、恶草灵、环丙氧磺隆、氯噁嗪草、乙氧氟草醚、百草枯、壬酸、二甲戊灵、Pendralin、戊噁唑草、甜菜宁、哌草磷、丙草胺、氟嘧磺隆(甲酯)、扑草净、毒草胺、敌稗、恶草酸、异丙草胺、炔苯酰草胺、苄草丹、氟磺隆、氟唑草酯(乙酯)、吡唑特、吡嘧磺隆(乙酯)、苄草唑、Pyribenzoxim、稗草丹、哒草特、肟啶草(甲酯)、嘧草硫醚(钠盐)、二氯喹啉酸、氯甲喹啉酸、灭藻醌、精喹禾灵乙酯、精喹禾糠酯、砜嘧磺隆、稀禾啶、西玛津、西草净、磺草酮、甲磺草胺、甲嘧磺隆(甲酯)、草硫磷、乙黄黄隆、牧草胺、丁噻隆、Tepraloxydim、特丁津、特丁净、噻吩草胺、Thiafluamide、噻唑烟酸、噻二唑胺、噻吩磺隆(甲酯)、禾草丹、仲草丹、三甲苯草酮、野麦畏、醚苯磺隆、苯磺隆(甲酯)、三氯吡氧乙酸、灭草环、氟乐灵和氟胺磺隆。
另外,本发明活性化合物可以其市售制剂和从上述制剂与增效剂混合制备的应用形式使用。增效剂是能够增加活性化合物活性的化合物,但加入的增效剂本身不是必须是有活性的。
从市售制剂制备的应用形式中活性化合物的含量可在很宽的范围内变化。应用形式中活性化合物的浓度为0.0000001至95%重量的活性化合物,优选0.0001至1%重量。
本发明化合物以适用于应用形式的常规方法进行使用。
所述活性化合物还适于防治有害生物,优选节肢动物和线虫,特别是在农业、林业、储藏产品和材料的保护以及卫生领域中发生的昆虫和螨类。它们对普通敏感和抗性种类害虫以及所有或某些发育阶段都具有活性。上述有害生物包括:
等足目,例如,潮虫(Oniscus asellus)、平甲虫和鼠妇。
倍足目,例如,具斑马陆。
唇足目,例如,食果地蜈蚣和蚰蜒属。
综合目,例如,庭园么蚰。
缨尾目,例如,台湾衣鱼。
弹尾目,例如,武装棘跳虫。
直翅目,例如,东方蜚蠊、美洲大蠊、马得拉蜚蠊、德国小蠊、家蟋蟀、蝼蛄属、非洲飞蝗、特异黑蝗和沙漠蝗。
革翅目,例如,欧洲球螋。
等翅目,例如,散白蚁属。
虱目,例如,葡萄根瘤蚜、瘿绵蚜属、体虱、血虱属和颚虱属。
食毛目,例如,嚼虱属和畜虱属。
缨翅目,例如,苜蓿蓟马、温室条蓟马、棕榈蓟马和烟蓟马。
异翅亚目,例如,扁盾蝽属、棉红蝽(Dysdercus intermedius)、方背皮蝽、温带臭虫、长红猎蝽和椎猎蝽属。
同翅目,例如,甘蓝粉虱、甘薯粉虱、温室白粉虱、棉蚜、甘蓝蚜、茶 隐瘤蚜、豆卫矛蚜、苹果蚜、苹果绵蚜、桃大尾蚜、葡萄根瘤蚜、瘿绵蚜属、麦长管蚜、瘤蚜属、忽布疣蚜、禾谷缢管蚜、绿小叶蝉属、殃叶蝉(Euscelis bilobatus)、黑尾叶蝉、欧果坚球蚧、榄珠蜡蚧、灰飞虱、褐飞虱、红肾圆盾蚧、常春藤圆盾蚧、粉蚧属、木虱属。
鳞翅目,例如,棉红铃虫、松粉蝶尺蛾、果园秋尺蛾、潜叶细蛾(lithocolletis blancardella)、苹果巢蛾、菜蛾、小菜蛾、黄褐天幕毛虫、黄毒蛾、毒蛾属、棉潜蛾(Bucculatrix thurberiella)、柑橘潜叶蛾、地夜蛾属、切夜蛾属、脏切夜蛾、埃及钻夜蛾、实夜蛾属、Spodoptera exigua、甘蓝夜蛾、小眼夜蛾、斜纹夜蛾、灰翅夜蛾属、粉纹夜蛾、苹果蠹蛾、粉蝶属、禾草螟属、玉米螟、地中海粉斑螟、蜡螟、幕谷蛾、袋谷蛾、褐织蛾、黄尾卷叶蛾、烟卷蛾(Capuareticulara)、云杉色卷蛾、葡萄果蠹蛾、茶长卷蛾、栎绿卷蛾、Cnaphalocerus属和水稻负泥虫。
鞘翅目,例如,家具窃蠹、谷蠹、菜豆象、北美家天牛、蓝毛臀萤叶甲、马铃薯叶甲、辣根猿叶甲、条叶甲属、油菜金头跳甲、墨西哥豆瓢虫、隐食甲属、锯谷盗、花象属、米象属、葡萄黑耳喙象、香蕉根颈象、种子象、紫苜蓿叶象、皮蠹属、斑皮蠹属、圆皮蠹属、毛皮蠹属、粉蠹属、油菜花露尾甲、蛛甲属、黄蛛甲、麦蛛甲、拟谷盗属、黄粉甲、叩甲属、宽胸叩甲属、五月鳃金龟、马铃薯鳃金龟、褐新西兰肋翅鳃角金龟和稻水象。
膜翅目,例如,松叶蜂属、实叶蜂属、毛蚁属、小家蚁和胡蜂属。
双翅目,例如,伊蚊属、按蚊属、库蚊属、黄猩猩果蝇、家蝇属、厕蝇属、红头丽蝇、绿蝇属、金蝇属、疽蝇属、胃蝇属、虱蝇属、斑潜蝇属、螫蝇属、狂蝇属、皮蝇属、虻属、螗蜩属(Tannia spp.)、花园毛蚊、瑞典麦杆蝇、草种蝇属、菠菜泉蝇、地中海实蝇、油橄榄果实蝇、沼泽大蚊、种蝇属和斑潜蝇属。
蚤目,例如,印鼠客蚤和角叶蚤属。
蛛形纲,例如,蝎(Scorpio maurus)和红斑蛛。
蜱螨目,例如,粗脚粉螨、锐缘蜱属、纯缘蜱属、鸡皮刺螨、兔瘿螨、柑橘皱叶刺瘿螨、牛蜱属、扇头蜱属、花蜱属、璃眼蜱属、硬蜱属、瘙螨属、痒螨属、疥螨属、跗线螨属、苜蓿苔螨、全爪螨属、叶螨属、半跗线螨属和短须螨属。
植物寄生线虫包括,例如短体线虫属、相似穿孔线虫、起绒草茎线虫、半穿刺线虫、异皮属、球异皮属、根结属、滑刃线虫属、长针线虫属、剑线属、毛刺属和伞滑刃线虫属。
本发明活性化合物在叶面和土壤施用后具有很高的杀虫和杀螨活性。
在一定的浓度或施用量条件下,本发明化合物还具有杀真菌活性。另外,它们还可以用作杀微生物剂或抗霉菌剂。
当用于防治卫生害虫和储藏物品中的害虫时,活性化合物具有优异的木材和粘土残留活性以及对石灰化底物上的碱具有很好的稳定性。
本发明活性化合物不仅对植物害虫、卫生害虫和储藏物品中的害虫具有活性,而且在兽医领域,对防治动物寄生虫(外寄生虫)也有活性,例如硬蜱、软蜱、兽疥癣螨、叶螨、蝇(叮咬和吸食)、寄生性蝇幼虫、虱、头虱、羽虱和跳蚤。这些寄生虫包括:
虱目,例如,血虱属、颚虱属、虱属、Pthirus spp.和管虱属;
食毛目以及钝角亚目和细角亚目,例如,毛羽虱属、Menoponspp.、巨毛虱属、羽虱属、Werneckiella spp.、Lepikentron spp.、畜虱属、嚼虱属和猫羽虱属;
双翅目以及长角亚目和短角亚目,例如,伊蚊属、按蚊属、库蚊属、蚋属、真蚋属、白蛉属、Lutzomyia spp.、库蠓属、斑虻属、瘤虻属、黄虻属、虻属、麻翅虻属、Philipomyia spp.、蜂虱蝇属、家蝇属、齿股蝇属、螫蝇属、角蝇属、莫蝇属、厕蝇属、舌蝇属、丽蝇属、绿蝇属、金蝇属、Wohlfahrtia spp.、麻蝇属、狂蝇属、皮蝇属、胃蝇属、虱蝇属、Lipoptena spp.和蜱蝇属
蚤目,例如,蚤属、栉首蚤属、印鼠客蚤属和角叶蚤属
异翅亚目,例如,臭虫属、椎猎蝽属、红腹猎蝽属和全圆蝽属
蜚蠊目,例如,东方蜚蠊,美洲大蠊,德国小蠊和蜚蠊属
蜱螨目以及后气门亚目和中气门亚目,例如,锐缘蜱属、纯缘蜱属、残喙蜱属、硬蜱属、花蜱属、牛蜱属、革蜱属、Haemophysalis spp.、璃眼蜱属、扇头蜱属、皮刺螨属、刺利螨属、肺剌螨属、胸孔螨属、瓦螨属
辐螨亚目(前气门亚目)和粉螨目(无气门亚目),例如,蜂跗线螨属、姬螫螨属、禽螫厘螨属、肉螨属、疮螨属、蠕形螨属、恙螨属、牦螨属、粉螨属、食酪螨属、嗜木螨属、颈下螨属、翅螨属、瘙螨属、痒螨属、耳螨属、疥螨属、痂螨属、疙螨属、胞螨属、皮膜螨属。
本发明式(I)活性化合物也适用于防治侵扰农业家畜的节肢动物,农业家畜如牛、绵羊、山羊、马、猪、驴、骆驼、水牛、兔、鸡、火鸡、鸭、鹅和蜜蜂,其它家养动物,例如狗、猫、笼养鸟和水族馆的鱼,还有所谓的试验动物,例如田鼠、豚鼠、大鼠和小鼠。通过防治上述节肢动物,旨在减少动物死亡和减产(肉、奶、毛、皮、蛋、蜜等)的情况发生,因此,通过使用本发明的活性化合物可以使动物饲养更经济而简便。
应用于兽医领域时,本发明活性化合物可通过已知方式经肠给药,例如以片剂、胶囊剂、饮剂、灌药剂、颗粒剂、膏剂、大丸剂、喂食方法和栓剂等形式给药;非经肠给药,例如通过注射(肌肉注射、皮下注射、静脉注射、腹膜内注射等),植入法给药;经鼻给药;经皮肤给药,例如以浸泡或药浴、喷雾、泼浇以及擦、洗涤和撒粉方式给药,也可借助于含有活性化合物的成型制品,例如项圈、耳饰物、尾饰物、肢环(带)、笼头、装饰器具等给药。
当用于家畜,家禽,宠物等时,式(I)活性化合物可以作为含有1-80%重量的活性化合物的制剂形式(例如粉剂,乳剂,流动组合物),直接或100至10000倍稀释后使用,或用作药浴。
另外,已发现本发明式(I)活性化合物还对损坏工业材料的昆虫具有很强的杀虫活性。
作为实例并优选列出下述昆虫,但并不限于此:
鞘翅目昆虫,如
北美家天牛、绿虎天牛(Chlorophorus pilosis)、家具窃蠹、报死材窃蠹、类翼窃蠹、Dendrobium pertinex、松芽枝窃蠹、松产品窃蠹(Priobium carpini)、褐粉蠹、粉蠹(Lyctus africanus)、南方粉蠹、栎粉蠹、粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylonaequale)、鳞毛粉蠹、材小蠹属、条木小蠹属、咖啡黑长蠹、Bostrychuscapucins、褐异翅长蠹、棘长蠹属和竹竿粉长蠹
膜翅目,例如
蓝黑树蜂、云杉大树蜂、泰加大树蜂和大树蜂(Urocerus augur)
白蚁,例如
木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁、印巴结构木异白蚁、欧美散白蚁、散白蚁(Reticulitermes santonensis)、散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁、内华达古白蚁和台湾乳白蚁
缨尾目,例如台湾衣鱼
本发明的工业材料可以理解为表示非生命(nicht-lebende)用品,例如优选塑料制品、粘合剂、浆(胶)料、纸和板、皮革、木材和加工后的木制品以及涂料组合物。
木材以及加工后的木制品是非常特别需要优选保护使其免受昆虫侵袭的材料。
可以通过本发明制剂或含有这些制剂的混合物保护的木材和木制品理解为表示,例如:建筑用木材、木梁、铁路轨枕、桥梁组件、船头、木制交通工具、箱子、货架、集装箱、电杆、木镶板、木窗和木门、胶合板、粗纸板、在房屋建筑或建筑细木工行业中常用的细木工或木制品。
活性化合物可以其本身,或以浓缩形式或常规制剂,如粉剂,颗粒剂,溶液,悬浮剂,乳剂或糊剂方式使用。
上述制剂可以本身已知方法制备,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,抗水剂混合,如需要加入干燥剂和UV稳定剂和如需要加入染料和颜料,和其它加工助剂。
用于保护木材和木制品的杀虫组合物或浓缩物中包含0.0001至95%重量,特别是0.001至60%重量浓度的本发明活性化合物。
组合物或浓缩物的使用量是根据昆虫的种类和个质密度以及介质情况而确定的。最佳施用量各自可通过应用中的系列试验确定。然而基于需保护的材料,通常使用0.0001至20%重量,优选0.001至10%重量的活性化合物是足够的。
使用的溶剂和/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类有机溶剂或溶剂混合物和/或极性有机溶剂或溶剂混合物和/或水,如需要可加入乳化剂和/或湿润剂。
优选使用的有机溶剂是油性或油类溶剂,蒸发值大于35以及闪点大于30℃,并优选大于45℃。用作上述低挥发度、不溶于水的油性和油类溶剂物质的是适合的矿物油或它们的芳族馏分,或含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
优选使用沸程为170-220℃的矿物油,沸程为170-220℃的石油溶剂,沸程为250-350℃的锭子油,沸程为160-280℃的石油和芳烃,以及松节油等。
在优选实施方案中,使用沸程为180-210℃的液体脂族烃或沸程为180-220℃的芳族和脂族烃的高沸程混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
蒸发值大于35以及闪点大于30℃并优选大于45℃的低挥发度的有机油性或油类溶剂可用高或中挥发度的有机溶剂部分替换,条件是溶剂混合物的蒸发值同样大于35以及闪点大于30℃并优选大于45℃,以及杀虫/杀真菌混合物可溶或可乳化于上述溶剂混合物中。
根据优选实施方案,某些有机化学溶剂或溶剂混合物用脂族极性有机化学溶剂或溶剂混合物替代。优选使用含有羟基和/或酯和/或醚基的脂族有机溶剂,例如二醇醚,酯等。
本发明使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干性油,它们可用水稀释和/或可溶解或分散或乳化于所使用的机化学溶剂中,特别是由下列物质组成或包含下列物质的粘合剂:丙烯酸盐树脂(Acrylatharz),乙烯基树脂,例如聚乙酸乙烯酯,聚酯类树脂,缩聚或聚加成树脂,聚氨酯树脂,醇酸树脂或改性的醇酸树脂,酚醛树脂,烃类树脂,如茚-香豆酮(Cumaron)树脂,有硅氧烷树脂,干性植物油和/或干性油和/或基于天然和/或合成树脂的物理干性粘合剂。
用作粘合剂的合成树脂可以乳剂,分散剂或溶液形式使用。沥青或沥青类物质也可用作粘合剂,用量至多为10%重量。还可以使用本身已知的染料,颜料,防水剂,气味调节剂和抑制剂或防腐剂等。
在本发明组合物或浓缩物中优选包含作为有机化学粘合剂的至少一种醇酸树脂或改性醇酸树脂和/或干性植物油。本发明优选使用含油量大于45%重量,优选50-68%重量的醇酸树脂。
上述所有或某些粘合剂可用固定剂(混合物)或增塑剂(混合物)替代。加入这些添加剂的目的是防止活性化合物的挥发以及结晶或沉淀。它们优选替代0.01至30%的粘合剂(以使用粘合剂的100%计)。
增塑剂得自邻苯二甲酸酯类的化学物质,如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄基丁基酯,磷酸酯类,如磷酸三丁酯,己二酸酯,如二-(2-乙基己基)己二酸酯,硬脂酸酯,如硬脂酸丁酯或硬脂酸戊酯,油酸酯,如油酸丁酯,甘油醚或高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂化学上基于聚乙烯烷基醚,如聚乙烯基甲基醚或酮,如二苯甲酮或亚乙基二苯甲酮。
作为适用的溶剂或稀释剂也特别是水,如需要可与一种或多种上述有机化学溶剂或稀释剂,乳化剂和分散剂混合使用。
特别有效的木材保护方法是通过大批量的浸渍方法,例如通过真空,双真空(Doppelvakuum)或加压方法。
现混现用(Anwendungsfertigen)组合物如适合还可以包含其它杀虫剂,和如适合还包含一种或多种杀真菌剂。
适合添加的混合组分优选WO94/29268中所提及的那些杀虫剂和杀真菌剂。在该文献中所述化合物也明确作为本申请的组成部分。
可提及的特别优选的混合组分是杀虫剂,如毒死蜱、辛硫磷、氟硅菊酯、顺式氯氰菊酯、氟氯氰菊酯、氯氰菊酯、溴氰菊酯、氯菊酯、吡虫啉、啶虫脒、氟虫脲、氟铃脲和杀铃脲,以及杀真菌剂,如氧唑菌、己唑醇、氧环唑、丙环唑、戊唑醇、环丙唑醇、叶菌唑、抑霉唑、抑菌灵、甲苯氟磺胺、3-碘-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。
本发明活性化合物可特别有效地防治侵染植物的害虫,如,例如,辣根猿叶甲(Phaedon cochleariae)的幼虫,黑尾叶蝉(Nephotettixcincticeps)的幼虫以及桃蚜(Myzus persicae)幼虫。
除了上述的杀螨,除草和杀虫活性外,本发明活性化合物的杀真菌活性也是显著的。在‘体外’和‘体内’试验中,都观察到广谱杀真菌活性。
而且,已经确定活性化合物还特别适用于防治侵染植物的霉菌(Mehltau),叶斑枯病菌(Blattflecken)以及镰孢霉属病菌(Fusarien)。
本发明活性化合物的制备及其应用如下列实施例所示。
制备实施例:
实施例1 化合物编号I-a-1
(方法C)
在60℃下,将0.9g 4-氯苯甲酰基乙腈和甲酸三甲酯的混合物与0.3g异丙胺混合。将反应混合物加热至125-130℃,通过薄层色谱法监控反应的进行。
在所有起始物转化后,使用旋转蒸发器浓缩反应混合物,将已生成的产物用二氯甲烷/NaHCO3溶液萃取。
通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(2∶1)分离溶液中所含化合物。
蒸发掉溶剂后,获得的主馏分之一,0.65g(收率为理论值的55%)的2-(4-氯苯甲酰基)-3-(N-甲基氨基)-丙烯腈,熔点为148℃。
实施例2 化合物编号I-a-59
(方法A)
首先加入0.7g 4-氯-苯甲酰基乙腈,0.5g N-甲基亚氨基乙酸甲酯和8ml甲苯的混合物并加热至80℃。将反应混合物在80℃搅拌10小时,然后蒸发溶剂浓缩,将所产生固体用甲基叔丁基醚/二氯甲烷重结晶。
获得0.51g(收率为理论值的54.9%)的2-(4-氯苯甲酰基)-3-(N-甲基氨基)-丁烯腈,熔点为152℃。
实施例3 化合物编号I-a-41
(方法A)
将1g N-甲基-4-氯亚氨基苯甲酸硫代甲酯和1g 4-氯苯甲酰基乙腈加入10ml甲苯中。将混合物搅拌4小时。全部转化后(TLC控制),通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(2∶1)分离混合物中所含的化合物。
蒸发掉溶剂后,获得的主馏分之一,1.30g的(收率为理论值的81%)的2-(4-氯苯甲酰基)-3-(4-氯苯基)-3-(N-甲基氨基)-丙烯腈,熔点为182℃。
实施例4 化合物编号III-a-1
在0℃下,将5g N-甲基-4-氯硫代苯甲酰胺溶解在乙腈中并与3.3g氢氧化钾混合。在20℃下,加入4g碘甲烷,然后将混合物加热至60℃。全部转化后(TLC控制),将反应混合物过滤并通过旋转蒸发器蒸发溶剂浓缩。
获得2.0g(收率为理论值的40%)的N-甲基-4-氯亚氨基苯甲酸硫甲酯,该化合物易于分解。
实施例5 化合物编号VI-a-1
在0℃,将80g N-甲基-4-氯-苯甲酰胺在600ml吡啶中与107g五硫化二磷混合。将混合物加热至80℃,然后保持在该温度下2小时。
通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(10∶1)分离混合物中所含的化合物。
蒸发掉溶剂后,获得的主馏分之一,46g的N-甲基-4-氯-硫代苯甲酰胺(收率为理论值的52%)。
实施例6
在-30℃下,将约200ml的甲胺压缩至400ml THF中。然后在-10℃至0℃,将反应溶液与75g 4-氯苯甲酰氯(使用它的30ml THF溶液)混合。20℃下,通过薄层色谱监控反应进度。
全部转化后,通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(2∶1)分离混合物中所含化合物。
蒸发掉溶剂后,获得主馏分,80g(收率为理论值的99%)的N-甲基-4-氯-苯甲酰胺。
实施例7 化合物编号I-a-60
将1g 4-氯苯甲酰基乙酰胺(公开在JP-A89-108491)和10ml原甲酸三甲酯混合并在90℃下反应1小时。冷却至60℃后,加入2ml异丙胺。然后将混合物在110℃下加热10分钟。全部转化后,通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(2∶1)分离混合物中所含化合物。
蒸发掉溶剂后,获得主馏分,0.2g(收率为理论值的7.5%)的2-(4-氯苯甲酰基)-3-(N-异丙基氨基)丙烯酰胺。1H-NMR(400MHz,d6-DMSO):δ=1.14(d,6H,CH(CH3)2),3.58(m,1H,
CH(CH3)2),7.16(d,br,1H,CONH),8.86(d,br,1H,CONH),10.83(br,1H,
NH)ppm,UV(乙腈/H3PO4缓冲梯度):λmax 244,292nm
实施例8 化合物编号I-a-61
(方法D)
在20℃,将0.8g 2-(4-氯苯甲酰基)-3-(N-环丙基氨基)-丁烯腈与0.7g Lawesson试剂混合并反应1小时。全部转化后,通过柱色谱的硅胶相使用流动相己烷/乙酸乙酯(2∶1)分离混合物中所含的化合物。
蒸发掉溶剂后,获得主馏分,0.7g(收率为理论值的84%)的2-[(4-氯苯基)-硫代羰基]-3-(N-环丙基氨基)-丁烯腈,熔点为215℃。
首先将30.0g 6-氟-4H-苯并[1,4]噁嗪-3-酮加入300ml的二氯甲烷,然后室温下逐滴缓慢加入37.4g溴。在30℃下边搅拌边加热混合物15小时。将反应溶液冷却至室温并倾至冰上。用二氯甲烷反复萃取水相。将合并的有机相用饱和硫代硫酸钠溶液洗涤,硫酸镁干燥并浓缩。获得44.1g(收率为理论值的99.5%)的7-溴-6-氟-4H-苯并[1,4]噁嗪-3-酮,熔点为244℃。
氩气氛围中,首先将25.5g 7-溴-6-氟-4H-苯并[1,4]噁嗪-3-酮加入120ml DMF中,在0℃,分批与28.0g碳酸钾混合。然后在0℃,逐滴加入13.0ml烯丙基溴,并将混合物在室温下搅拌15小时。将混合物倾入1200ml冰水中并用乙酸乙酯反复萃取,将合并的有机相用饱和氯化钠水溶液洗涤,硫酸镁干燥,浓缩。
使用硅胶柱色谱(流动相:乙酸乙酯/环己烷1∶1)纯化粗产物,获得2 3.8g(产率为理论值的81.9%)N-烯丙基-7-溴-6-氟-4H-苯并[1,4]噁嗪-3-酮,熔点92℃。
实施例11 化合物编号(XIV-b-2)
首先将20.0g N-苄基-7-甲氧基羰基-4H-苯并[1,4]噁嗪-3-酮加入750ml的MeOH中。室温下,逐滴加入35ml 2N氢氧化钠水溶液,将混合物在40-55℃下搅拌30小时。将反应溶液冷却至室温并倾入200ml 1NHCl和1kg冰的混合物中。抽吸过滤粗产物,用水洗涤并干燥。获得18.2g(收率为理论值的95.5%)的N-苄基-7-羟基羰基-4H-苯并[1,4]噁嗪-3-酮,熔点为230℃。
类似上述制备实施例并根据制备式(I)化合物的一般性描述可以制备下列化合物: 表1 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续) 表1(续)
化合物编号 | Gn | Y | Z | 熔点℃ |
I-a-172 | 3,5-(CF3)2 | CH2CH(CH3)C2H5 | H | 119 |
表中,“Me”代表甲基(CH3)。
类似制备实施例4以及根据制备式(III)化合物的一般性描述可以制备下列化合物:
化合物编号 | R8 | Y | Rg | 熔点℃ |
IIIa-1 | CH3 | CH3 | 4-Cl | 油 |
III-a-2 | CH3 | Ally1 | H | 油 |
III-a-3 | CH3 | Ally1 | 4-Cl | 油 |
III-a-4 | CH3 | i-C3H7 | 4-Cl | 油 |
III-a-5 | CH3 | C2H5 | 4-Cl | 油 |
III-a-6 | CH3 | CH2-CF3 | 4-Cl | 油 |
类似制备实施例5以及根据制备式(VI)化合物的一般性描述可以制备下列化合物:
化合物编号 | Y | Rg |
VI-a-1 | CH3 | 4-Cl |
VI-a-2 | i-C3H7 | 4-Cl |
VI-a-3 | Ally1 | 4-Cl |
VI-a-4 | C2H5 | 4-Cl |
VI-a-5 | CH2-CF3 | 4-Cl |
实施例
苗后处理试验
溶剂: 5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂混合,并加入上述量的乳化剂,然后将浓缩物用水稀释至所需浓度。
将长至5-15cm高的测试植物用活性化合物制剂喷雾以使每单位面积上能够施用各所需的一定量的活性化合物。三周后,与未处理对照的发育情况相比评价植物的伤害程度,以%伤害表示。
下列数字表示:
0%=没有活性(类似于未处理对照)
100%=全部杀死
在该试验中,例如制备实施例I-a-35,I-a-20,I-a-4,I-a-17,I-a-3,I-a-59,I-a-58,I-a-29,I-a-8和I-a-23的化合物表现出很强的除草活性,并且作物例如小麦对一些化合物具有很好的耐受性。
实施例
苗前处理试验
溶剂: 5重量份丙酮
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂混合,并加入上述量的乳化剂,然后将浓缩物用水稀释至所需浓度。
将测试植物的种子播种在正常土壤中,24小时后,用活性化合物制剂灌注土壤。优选每单位面积的用水量保持恒定。制剂中活性化合物浓度是不重要的,关键是每单位面积活性化合物的施用量。三周后,与未处理对照的发育情况相比评价植物的伤害程度,以%伤害表示。
下列数字表示:
0%=没有活性(类似于未处理对照)
100%=全部杀死
在该试验中,例如制备实施例I-a-3,I-a-17,I-a-20,I-a-4,I-a-58,I-a-59,I-a-23,I-a-8和I-a-21的化合物表现出很强的除草活性,并且作物例如小麦和大豆对一些化合物具有很好的耐受性。
实施例A
根结线虫(Meloidogyne)试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用水稀释浓缩物至所需浓度。
向容器中装填砂子,活性化合物溶液,南方根结线虫(Meloidogyneincognita)卵/幼虫悬浮液以及莴苣种子(Salatsamen)。莴苣种子萌发且植株发育。在莴苣的根部,形成虫瘿。
在预定的一段时间后,测定杀线虫活性,以形成虫瘿%作为计量单位。100%表示没有发现虫瘿;0%表示处理后植物上的虫瘿数量相当于未处理对照的虫瘿数量。
在该试验中,例如制备实施例中的下列化合物表现出很好的活性:
I-a-39,I-a-42,I-a-5
实施例B
猿叶甲(Phaedon)幼虫试验
溶剂: 30重量份二甲基甲酰胺
乳化剂:1重量份烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将卷心菜叶片(Brassica oleracea)浸在所需浓度的活性化合物制剂中进行处理并在菜上定殖辣根猿叶甲(Phaedon cochleariae)幼虫同时一直保持叶片湿润。
在预定的一段时间后,测定杀虫活性%。100%意为已杀死所有辣根猿叶甲(Kferlarven)幼虫;0%意为没有杀死一头辣根猿叶甲幼虫。
在此试验中,例如制备实施例中的下述化合物表现出很好的活性:
I-a-13,I-a-39,I-a-44,I-a-15,I-a-19,I-a-53。
实施例C
小菜蛾(Plutella)试验
溶剂: 30重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将卷心菜叶片(Brassica oleracea)浸在所需浓度的活性化合物制剂中进行处理并在菜上定殖小菜蛾(Plutella xylostella)幼虫同时保持叶片湿润。
在预定的一段时间后,测定杀虫活性%。100%意为已杀死所有幼虫;0%意为没有杀死一头幼虫。
在此试验中,例如制备实施例中的下述化合物表现出很好的活性:
I-a-58,I-a-45。
实施例D
草地粘虫(Spodoptera frugiperda)试验
溶剂:30重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将卷心菜叶片(Brassica oleracea)浸在所需浓度的活性化合物制剂中进行处理并在菜上定殖草地粘虫的幼虫同时保持叶片湿润。
在预定的一段时间后,测定杀虫活性%。100%意为已杀死所有幼虫;0%意为没有杀死一头幼虫。
在此试验中,例如制备实施例中的下述化合物表现出很好的活性:
I-a-42,I-a-45,I-a-48,I-a-18,I-a-52。
实施例E
叶螨(Tetranychus)试验(OP-抗性/浸渍处理)
溶剂: 7重量份的二甲基甲酰胺
乳化剂:1重量份的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1重量份活性化合物与上述量的溶剂和乳化剂混合,并用含有乳化剂的水稀释浓缩物至所需浓度。
将被二点叶螨(Tetranychus urticae)的所有发育阶段严重侵染的菜豆(Phaseolus vulgaris)植株浸渍在所需浓度的活性化合物制剂中。
在预定的一段时间后,测定杀螨活性%。100%意为已杀死所有的螨;0%意为没有杀死一头螨。
在此试验中,例如制备实施例中的下述化合物表现出很好的活性:
I-a-3。
Claims (10)
1.通式(I)化合物其中
K代表氧或硫,
Ar代表各自任选取代的苯基,萘基,代表各自任选取代的具有5-10个环原子的单-或双环的杂芳基,或代表基团其中
B1代表氢或卤素,
两个相邻基团-B2和B3或B3和B4-一起代表下列基团之一
-Q1-CQ2-,-Q1-CQ2-Q3,-Q1-C(B6,B7)-Q3-,-C(B6,B7)-CQ2-,
-C(B6,B7)-Q1-CQ2-,-Q1-C(B6,B7)-C(B6,B7)-,
-Q1-C(B6,B7)-C(B6,B7)-Q3-,-C(B6,B7)-C(B6,B7)-CQ2-,
-Q1-C(B6)=C(B6)-,-C(B6)=C(B6)-CQ2-,-Q1-C(B6,B7)-CQ2-,
-N(B8)-C(B6,B7)-CQ2-,-C(B6)=N-,-Q1-CQ2-C(B6,B7)-,
-Q1-CQ2-N(B8)-,-Q1-C(B6,B7)-CQ2-N(B8)-,
-C(B6,B7)-Q1-CQ2-N(B8)-,-C(B6,B7)-C(B6,B7)-N(B8)-,
-C(B6,B7)-C(B6,B7)-CQ2-N(B8)-,-C(B6)=C(B6)-N(B8)-,
-C(B6)=C(B6)-CQ2-N(B8)-,-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-C(B6,B7)-CQ2-N(B8)-,-C(B6)=N-N(B8)-,
-Q1-CQ2-C(B6,B7)-N(B8)-,-Q1-C(B6,B7)-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-CQ2-C(B6)=N-,-Q1-C(B6)=C(B6)-Q3-,
-N(B8)-C(B6)=C(B6)-CQ2-,
-N(B8)-C(B6)=N-,-N(B8)-C(B6,B7)-C(B6,B7)-Q3-,
-N(B8)-CQ2-C(B6,B7)-Q4-,-N(B8)-CQ2-CQ2-Q3-,
-Q1-C(B6)=C(B6)-C(B6,B7)-,-Q1-C(B6)=C(B6)-,
和第四个基团,B4或B2,代表氢,硫代氨甲酰基,氰基或卤素,
其中
Q1,Q2和Q3相同或不同,并各自代表氧或硫,和
Q4代表-SO-或-SO2-,
B6和B7相同或不同并各自代表氢,卤素或烷基或一起代表链烷二基,和
B8代表氢,羟基,代表各自任选氰基-,卤素-,烷氧基-,烷基羰基-或烷氧基羰基-取代的烷基,烷基羰基,烷氧基羰基,烷硫基或烷基磺酰基,代表各自任选卤素-取代的烯基或炔基,代表各自任选卤素-或烷基-取代的环烷基或环烷基烷基,代表各自任选卤素取代的烷氧基或烯氧基,代表各自任选氰基-,卤素-,烷基-,卤代烷基-,烷氧基-或卤代烷氧基取代的芳烷基或芳烷氧基,X代表CN,
或
Y代表氢,代表各自任选取代的烷基,烯基,炔基,烷氧基烷基,烷硫基烷基,代表各自任选取代的环烷基或环烷基烷基,上述的环烷基或环烷基烷基各自任选在其环上被杂原子间断,或代表各自任选取代的苯基烷基或杂芳基烷基,
Z代表氢,代表各自任选取代的烷基,苯基或苯基烷基,
R1代表氢,代表各自任选取代的饱和或不饱和的、各自任选被杂原子间断的烷基或环烷基,代表各自任选取代的苯基或杂芳基,代表各自任选取代的苯基烷基或杂芳基烷基,和
R2代表氢,代表各自任选取代的饱和或不饱和的烷基或烷氧基,代表各自任选取代的苯基,苯基烷基或苯基烷氧基,或
R1,R2还与它们所连接的氮原子一起代表任选取代的环,该环任选被一个或多个杂原子间断。
2.权利要求1的化合物,其特征在于
Ar代表Ar1,其中Ar1代表苯基,萘基或具有五至十个环原子的单-或双环的杂芳基,各基团任选被下列基团一-至五取代:卤素,C1-C8-烷基,C2-C8-烯基,C2-C8-炔基,C1-C8-烷氧基,C2-C8-烯氧基,C3-C8-炔氧基,C1-C8-烷硫基,C1-C6-烷基磺酰基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C2-C8-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C4-烷硫基,卤代-C1-C4-烷基磺酰基,苯基-C1-C4-烷氧基,羟基,巯基,硝基,氰基,氨基或下述基团
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,萘基,五-或六员杂芳基,苯基-C1-C4-烷基,苯氧基,苯基-S(O)g-,五或六员杂芳氧基或杂芳基-S(O)g,其中就其本身来说这些取代基各自任选被下列基团一-至四取代: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,其中g代表0,1或2,
或代表基团其中
B1代表氢或卤素,
两个相邻的基团-B2和B3或B3和B4-一起代表下列基团之一
-Q1-CQ2-N(B8)-,-Q1-C(B6,B7)-CQ2-N(B8)-,
-N(B8)-C(B6,B7)-CQ2-N(B8)-,-Q1-CQ2-C(B6,B7)-N(B8)-,
-Q1-C(B6)=C(B6)-C(B6,B7)-,-Q1-C(B6)=C(B6)-,
-N(B8)-CQ2-C(B6)=N-其中
Q1和Q2相同或不同并各自代表氧或硫,
B6和B7相同或不同并各自代表氢或甲基,
B8代表氢,羟基,代表各自任选氰基-,氟-,氯-,甲氧基-,乙氧基-,乙酰基-,丙酰基-,甲氧基羰基-或乙氧基羰基-取代的甲基,乙基,正-或异丙基,正-,异-,仲-或叔丁基,代表各自任选氟-,氯-或溴取代的丙烯基,丁烯基,丙炔基或丁炔基,代表各自任选氟-,氯-,溴-,甲基-或乙基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,代表各自任选氟-和/或氯-取代的甲氧基,乙氧基,正-或异丙氧基,正-,异-或仲丁氧基,丙烯氧基或丁烯氧基,或代表各自任选氰基-,氟-,氯-,甲基-,乙基-,三氟甲基-,甲氧基-,乙氧基-,二氟甲氧基-或三氟甲氧基取代的苄基或苄氧基,
和第四个基团,B4或B2,代表氢,氰基,氟或氯,
K代表氧或硫。
L代表氧或硫。
Y代表氢,各自任选一-或多羟基取代的C1-C12-烷基,C3-C10-烯基,C3-C10-炔基,C1-C6-烷氧基-C2-C4-烷基,二-C1-C6-烷氧基-C2-C4-烷基,C1-C6-烷氧基-C2-C4-氰基烷基,C1-C6-烷硫基-C2-C4-烷基,C1-C8-卤代烷基,C1-C8-卤代烯基或C1-C8-氰基烷基,代表各自任选下列基团取代的、任选环上被氧,硫或氮间断的C3-C8-环烷基或C3-C8-环烷基-C1-C4-烷基:C1-C6-烷基-,C1-C6-烷氧基-,C1-C4-卤代烷基-,氰基-,卤代苯基-,苄基-,C1-C6-羟基烷基-或卤素,代表苯基-C1-C4-烷基或五-或六员杂芳基-C1-C4-烷基,各基团任选被卤素,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,
Z代表氢,C1-C6-烷基,代表苯基或苯基-C1-C4-烷基,各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基一至三取代,
R1代表氢,代表各自任选氟-和/或氯取代的C1-C10-烷基,C3-C10-烯基,C3-C6-炔基,代表各自任选氟-,氯-,C1-C4-烷基-,C1-C1-烷氧基-取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C5-C8-环烯基,或代表苯基,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,各基团任选被卤素,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。
R2代表氢,C1-C6-烷基或C3-C6-烯基或
R1,R2还与它们所连接的氮原子一起代表各自任选C1-C4-烷基取代的五-至八员环,其中该环任选一个亚甲基可被氧或硫替换,
R3代表各自任选氟-和/或氯取代的C1-C10-烷基,C2-C10-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,各自任选氟-,氯-,C1-C4-烷基-和/或C1-C4-烷氧基取代的、任选一个亚甲基可被氧或硫替换的C3-C8-环烷基或C3-C8-环烷氧基,代表苯基,苯氧基,苄氧基,五-或六员杂芳基或苯基-C1-C4-烷基,各基团任选被卤素,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,或当为Ar中所述基团a),c)和f)的情况下,还代表下列基团
R4代表氢或C1-C4-烷基,
R5代表氢或任选氟-和/或氯取代的C1-C4-烷基,
R6代表氢,各自任选氟-和/或氯取代的C1-C10-烷基,C3-C8-烯基,C3-C8-炔基,C1-C10-烷氧基,C3-C8-烯氧基,任选下列基团取代的任选一个亚甲基被氧或硫替换的C3-C8-环烷基:氟-,氯-,C1-C4-烷基-或C1-C4-烷氧基-,代表苯基,苯基-C1-C4-烷基或苯基-C1-C2-烷氧基,各基团任选被卤素,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,
R7代表氢,C1-C6-烷基或C3-C6-烯基,或
R6,R7还与它们所连接的氮原子一起代表任选C1-C4-烷基取代的五-至八员环,该环任选一个亚甲基可被氧或硫替换。
3.权利要求1的化合物,其特征在于
K代表氧或硫,
Ar代表Ar1,其中Ar1代表苯基,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,各基团任选被下列基团一-至三取代:氟,氯,溴,C1-C6-烷基,C2-C6-烯基,C2-C6-炔基,C1-C6-烷氧基,C3-C6-烯氧基,C3-C6-炔氧基,C1-C6-烷硫基,C1-C4-烷基磺酰基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,C2-C4-卤代烯氧基,C1-C2-亚烷二基-二氧基,C1-C2-卤代亚烷二基-二氧基,卤代-C1-C2-烷硫基,卤代-C1-C2-烷基磺酰基,苯基-C1-C4-烷氧基,羟基,巯基,硝基,氰基,氨基或下列基团之一
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1: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-,吡啶氧基,嘧啶氧基,噻唑氧基,吡啶基-S(O)g-,嘧啶基-S(O)g-或噻唑基-S(O)g-,其中就其本身来说这些取代基任选被下列基团一-至三取代:氟,氯,溴,C1-C4-烷基,C2-C4-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,其中g代表0,1或2,
或代表基团其中
B1代表氢或卤素,
两个相邻基团-B2和B3或B3和B4一起代表下列基团
-Q1-C(B6,B7)-CQ2-N(B8)-,其中
Q1和Q2相同或不同并各自代表氧或硫,
B6和B7相同和不同并各自代表氢或甲基,
B8代表氢,羟基,代表各自任选氰基-,氟-,氯-,甲氧基-,乙氧基-,乙酰基-,丙酰基-,甲氧基羰基-或乙氧基羰基-取代的甲基,乙基,正或异丙基,正-,异-,仲或叔丁基,代表各自任选氟-,氯-或溴-取代的丙烯基,丁烯基,丙炔基或丁炔基,代表各自任选氟-,氯-,溴-,甲基-或乙基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,代表各自任选氟-和/或氯-取代的甲氧基,乙氧基,正-或异丙氧基,正-,异-或仲丁氧基,丙烯氧基或丁烯氧基,或代表各自任选氰基-,氟-,氯-,甲基-,乙基-,三氟甲基-,甲氧基-,乙氧基-,二氟甲氧基或三氟甲氧基取代的苄基或苄氧基,
和第四个基团,B4或B2,代表氢,氰基,氟或氯,
Y代表氢,代表各自任选一-或多羟基取代的C1-C10-烷基,C1-C6-卤代烷基,C3-C8-烯基,C3-C8-炔基,C1-C4-烷氧基-C2-C3-烷基,二-C1-C4-烷氧基-C2-C4-烷基,C1-C4-烷氧基-C2-C4-氰基烷基,C1-C4-烷硫基-C2-C3-烷基,C1-C6-卤代烯基或C1-C6-氰基烷基,代表各自任选下列基团取代的、任选一个亚甲基可被氧或氮替换的C3-C6-环烷基或C3-C6-环烷基-C1-C2-烷基:C1-C4-烷基-,C1-C4-烷氧基-,C1-C2-卤代烷基-,氰基-,卤代苯基-,苄基-,C1-C4-羟基烷基-,氟-或氯,代表苯基-C1-C3-烷基,噻唑基甲基,三唑基甲基或吡啶基甲基,各自任选被下列基团一-至三取代: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,
Z代表氢,C1-C3-烷基,代表各自任选被下列基团一-或二取代的苯基或苄基: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,
R1代表氢,代表各自任选氟和/或氯取代的C1-C6-烷基,C2-C6-烯基,C3-C4-炔基,代表任选氟-,氯-,C1-C2-烷基-,C1-C2-烷氧基-取代的C3-C6-环烷基或代表各自任选被下列基团一-或二取代的苯基或苄基: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,
R2代表氢,代表各自任选被氟和/或氯取代的C1-C4-烷基或C3-C4-烯基,或
R1,R2还与它们所连接的氮原子一起代表任选甲基取代的五-或六员环,其中任选一个亚甲基可被氧替换,
R3代表各自任选氟-和/或氯-取代的C1-C6-烷基,C2-C6-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,各自任选氟-,氯-,C1-C2-烷基-和/或C1-C2-烷氧基取代的、任选一个亚甲基可被氧替换的C3-C6-环烷基或C3-C6-环烷氧基,代表各自任选被下列基团一-或二取代的苯基,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: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,或为Ar中所列的基团a),c)和f)时,还代表基团
R4代表氢,
R5代表氢,甲基或乙基,
R6代表氢,各自任选氟-和/或氯-取代的C1-C6-烷基,C3-C6-烯基,C3-C6-炔基,C1-C6-烷氧基,C3-C6-环烷基,其中任选一个亚甲基可被氧替换,代表各自任选被下列基团一-或二取代的苯基或苯基-C1-C2-烷基: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,
R7代表氢或C1-C4-烷基,或
R6,R7还与它们连接的氮原子一起代表任选C1-C2-烷基-取代的五-或六员环,该环中任选一个亚甲基可被氧替换。
4.权利要求1的化合物,其特征在于
K代表氧或硫,
Ar代表Ar1,其中Ar1代表任选被下列基团一-至三取代的苯基:氟,氯,溴,甲基,乙基,丙基,异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,丙氧基,异丙氧基,仲-,正-,异-或叔丁氧基,烯丙氧基,甲代烯丙氧基,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,亚甲二氧基,二氟亚甲二氧基,四氟亚乙二氧基,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,苄氧基,羟基,巯基,硝基,氰基或氨基,或代表任选被下列基团一-或二取代的吡啶基:氟,氯,溴,甲基,乙基,甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,甲硫基,乙硫基或三氟甲基,
或代表Ar2,其中Ar2代表另外被下列基团取代的Ar1:苯基,吡啶基,噻吩基,四唑基,三唑基或苯氧基,其中就其本身来说这些取代基还任选被下列基团一-或二取代:氟,氯,溴,甲基,乙基,正-或异丙基,仲-,正-,异-或叔丁基,甲氧基,乙氧基,异丙氧基,仲-,正-或叔丁氧基,三氟甲基,三氟甲氧基,硝基或氰基,
或代表基团
其中B1代表氢或氟和B8代表烯丙基,炔丙基或苄基,
Y代表氢,各自任选一-或多羟基取代的C1-C6-烷基,C1-C4-卤代烷基,C3-C6-烯基,C3-C6-炔基,C1-C4-烷氧基-C2-C3-烷基,二-C1-C2-烷氧基-C2-C4-烷基,C1-C2-烷氧基-C2-C4-氰基烷基,C1-C2-烷硫基-C2-C3-烷基,C1-C5-卤代烯基或C1-C6-氰基烷基,代表各自任选甲基-,甲氧基-,乙氧基-,三氟甲基-,氰基-,氯苯基-,苄基-,羟甲基-,氟-或氯-取代的、其中任选一个亚甲基可被氧或硫替换的C3-C6-环烷基或C3-C6-环烷基-C1-C2-烷基,代表各自任选被下列基团一-至三取代的苄基,苯乙基或吡啶甲基:氟,氯,溴,甲基,甲氧基,三氟甲基,二氟甲氧基,三氟甲氧基,氰基或硝基,
Z代表氢,甲基,乙基,代表各自任选被下列基团一-或二取代的苯基或苄基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基,
R3代表甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,乙烯基,三氟甲基,甲氧基,乙氧基,丙氧基,异丙氧基,正-,仲-,异-或叔丁氧基,环丙基,环戊基,环己基,环戊氧基,环己氧基,代表各自任选被下列基团一-或二取代的苯基,吡啶基或苄基:氟,氯,溴,甲基,正-,仲-,异-或叔丁基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基,或为Ar中所列的基团a),c)和f)的情况下,还代表基团
R5代表氢或甲基,
R6代表氢,甲基,乙基,丙基,异丙基,正-,仲-,异-或叔丁基,环丙基,环戊基,环己基,代表任选被下列基团一-或二取代的苯基:氟,氯,溴,甲基,甲氧基,三氟甲基,三氟甲氧基,氰基或硝基,
R7代表氢,甲基或乙基,或
R6,R7与它们连接的氮原子一起还代表吡咯烷基,哌啶基或吗啉基。
6.根据权利要求1-5中任一项的化合物的制备方法,其特征在于
(A)如果K代表氧,
将式(II)化合物其中
Ar和X如权利要求1-5中任一项的定义,
与式(III)化合物反应其中
Y和Z如权利要求1-5中任一项的定义但不代表氢,
和
W代表O或S(O)g,其中g代表0或2,和
R8代表烷基或苄基,
如适合在存在稀释剂和如适合在存在碱或式(IVa)的金属化合物的条件下进行上述反应
Me(V)2 (IVa)其中
Me代表二价过渡金属原子,和
V代表螯合配位体,
或
(B)如果K代表氧,
Ar和X如如权利要求1-5中任一项的定义,
和
Hal代表卤素,
Y和Z如权利要求1-5中任一项的定义,但不代表氢,
Ar,X,Y和Z如上定义,
其如适合在存在碱和如适合存在三价磷化合物的条件下,进一步反应,消除硫和卤化氢获得式(I)化合物
其中
Ar,X,Y和Z如上定义
或
(C)首先将式(II)化合物其中
Ar和X如权利要求1-5中任一项的定义,
与式(VIII)化合物缩合
其中Z如上定义和
R9代表C1-C4-烷基,
并将所得中间体与式(IX)的胺反应
Y-NH2 (IX)其中
Y如权利要求1-5中任一项的定义,
如适合在存在稀释剂和如适合存在碱的条件下进行反应
或
(D)如果K代表硫,
可通过下述方法,即将式(I)化合物其中
Ar,X,Y和Z如权利要求1-5中任一项的定义和
K代表氧,
在存在硫化试剂如,例如五硫化二磷或2,4-双(4-甲氧基苯基)-1,2,3,4-二硫杂磷杂环丁烷2,4-硫化物(Lawesson试剂),存在溶剂的条件下反应制备,
或
(E)如果Ar代表如权利要求1-5中任一项的Ar2,
可通过下述方法获得,即在存在溶剂,如适合在存在碱和/或贵金属络合物的条件下
Ar1,X,Y和Z如权利要求1-5中任一项的定义和
Hal代表卤素,
与式(X)的硼酸反应
Ar2’-B(OH)2 (X),
其中
Ar2’代表权利要求1中作为对Ar1的另外的取代基所列的取代基。
7.除草剂,杀螨剂和/或杀虫剂组合物,其特征在于它们包含至少一种权利要求1-5中任一项的化合物和常用填充剂和/或表面活性剂。
8.权利要求1-5中任一项的化合物防治不需要植物和/或有害生物的用途。
9.防治不需要植物和/或有害生物的方法,其特征在于将权利要求1-5中任一项的化合物施用于不需要的植物或有害生物和/或它们的栖息地。
10.除草组合物的制备方法,其特征在于将权利要求1-5中任一项的化合物与常用填充剂或表面活性剂混合。
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CN103354807A (zh) * | 2010-11-15 | 2013-10-16 | 拜耳知识产权有限责任公司 | 氰基烯胺及其作为杀真菌剂的用途 |
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 |
CN111848449A (zh) * | 2019-04-30 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 一种新的酰氧基烯胺化合物 |
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US7812163B2 (en) | 2003-07-16 | 2010-10-12 | Hatchtech Pty Ltd. | Methods and compositions for controlling ectoparasites |
AU2003903686A0 (en) * | 2003-07-16 | 2003-07-31 | Hatchtech Pty Ltd | Methods and compositions for controlling ectoparasites |
WO2010055474A2 (en) * | 2008-11-13 | 2010-05-20 | Ariel-University Research And Development Company Ltd. | Antimicrobial compounds and compositions |
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US10292389B2 (en) | 2013-12-17 | 2019-05-21 | Dr. Reddy's Laboratories, S.A. | Pediculicidal composition |
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Cited By (3)
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---|---|---|---|---|
CN103354807A (zh) * | 2010-11-15 | 2013-10-16 | 拜耳知识产权有限责任公司 | 氰基烯胺及其作为杀真菌剂的用途 |
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 |
CN111848449A (zh) * | 2019-04-30 | 2020-10-30 | 帝斯曼知识产权资产管理有限公司 | 一种新的酰氧基烯胺化合物 |
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PL366218A1 (en) | 2005-01-24 |
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US7049271B2 (en) | 2006-05-23 |
BR0110632A (pt) | 2003-03-18 |
MXPA02010925A (es) | 2003-04-14 |
US20030220196A1 (en) | 2003-11-27 |
US20060100106A1 (en) | 2006-05-11 |
ZA200207953B (en) | 2004-03-29 |
DE10021900A1 (de) | 2001-11-15 |
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JP2004535356A (ja) | 2004-11-25 |
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