CN1225092A - 新的取代的吡啶基酮烯醇 - Google Patents
新的取代的吡啶基酮烯醇 Download PDFInfo
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- CN1225092A CN1225092A CN97196293A CN97196293A CN1225092A CN 1225092 A CN1225092 A CN 1225092A CN 97196293 A CN97196293 A CN 97196293A CN 97196293 A CN97196293 A CN 97196293A CN 1225092 A CN1225092 A CN 1225092A
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- alkyl
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- -1 pyridyl keto enols Chemical class 0.000 title claims abstract description 154
- 229930194542 Keto Natural products 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 157
- 150000001875 compounds Chemical class 0.000 claims description 221
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 121
- 239000000460 chlorine Substances 0.000 claims description 100
- 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
- 238000006243 chemical reaction Methods 0.000 claims description 78
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 150000002367 halogens Chemical class 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 67
- 125000003545 alkoxy group Chemical group 0.000 claims description 66
- 239000002585 base Substances 0.000 claims description 62
- 239000001301 oxygen Substances 0.000 claims description 61
- 229910052760 oxygen Inorganic materials 0.000 claims description 61
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 56
- 229910052721 tungsten Inorganic materials 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 229910052720 vanadium Inorganic materials 0.000 claims description 52
- 239000005864 Sulphur Substances 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 47
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 46
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 46
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 45
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 43
- 239000003513 alkali Substances 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 239000011230 binding agent Substances 0.000 claims description 29
- 229910052796 boron Inorganic materials 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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 20
- 150000002148 esters Chemical class 0.000 claims description 19
- 125000001544 thienyl group Chemical group 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 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 241000238631 Hexapoda Species 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 229940126062 Compound A Drugs 0.000 claims description 9
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 6
- 150000001345 alkine derivatives Chemical class 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 3
- 241000405414 Rehmannia Species 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 26
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 5
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000000575 pesticide Substances 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 description 65
- 229910052731 fluorine Inorganic materials 0.000 description 65
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 125000006414 CCl Chemical group ClC* 0.000 description 56
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 34
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000003999 initiator Substances 0.000 description 33
- 239000000463 material Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 238000006073 displacement reaction Methods 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
- 239000000370 acceptor Substances 0.000 description 16
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 16
- 230000008569 process Effects 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000003851 azoles Chemical class 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 150000002170 ethers Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 description 11
- 235000010755 mineral Nutrition 0.000 description 11
- 239000011707 mineral Substances 0.000 description 11
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 9
- 239000012973 diazabicyclooctane Substances 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 9
- 239000002798 polar solvent Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 235000015320 potassium carbonate Nutrition 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 8
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 8
- 241000219146 Gossypium Species 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 8
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 235000009566 rice Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 8
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 8
- 239000002023 wood Substances 0.000 description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 7
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 230000005595 deprotonation Effects 0.000 description 7
- 238000010537 deprotonation reaction Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 150000005826 halohydrocarbons Chemical class 0.000 description 7
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 241001674048 Phthiraptera Species 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 241001481703 Rhipicephalus <genus> Species 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 150000001733 carboxylic acid esters Chemical class 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
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- 235000010446 mineral oil Nutrition 0.000 description 6
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 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 6
- 238000012360 testing method Methods 0.000 description 6
- 238000009333 weeding Methods 0.000 description 6
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 239000005946 Cypermethrin Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 241001259047 Trichodectes Species 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 5
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 5
- 229960005424 cypermethrin Drugs 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 229940031815 mycocide Drugs 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 4
- 241000238679 Amblyomma Species 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 241001414720 Cicadellidae Species 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 241000832180 Hylotrupes bajulus Species 0.000 description 4
- 241000257303 Hymenoptera Species 0.000 description 4
- 241000256602 Isoptera Species 0.000 description 4
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- 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
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- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- 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
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/56—Amides
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Abstract
本发明涉及式(Ⅰ)新的吡啶基-取代的环酮烯醇。其中V1,V2或V3代表氮原子,Hel代表右面(1)~(5)式的基团之一,A,B,G,W,Z和z具有说明书中给出的定义,涉及其多种制备方法和中间体,并且涉及其作为杀虫剂和除草剂的用途。
Description
本发明涉及新的吡啶基-取代的环酮烯醇,其多种制备方法和中间体,以及涉及其作为杀虫剂和除草剂的用途。
迄今没有公开过吡啶基-取代的杂环酮烯醇。已知的是,一些苯基取代的环酮烯醇是有杀虫,杀螨和/或除草活性的。
已经公开了具有除草,杀虫或杀螨作用的未取代的,双环3-芳基-吡咯烷-2,4-二酮衍生物(EP-A-355599和EP-A-415211)和取代的单环3-芳基-吡咯烷-2,4-二酮衍生物(EP-A-377893和EP-A-442077)。
此外,已经公开了多环3-芳基吡咯烷-2,4-二酮衍生物(EP-A442073)和1H-芳基吡咯烷二酮(EP-A-456063,EP-A-521 334,EP-A-596298,EP-A-613884,EP-A-613885,DE-4440594,WO94/01997,WO95/01358,WO95/20572,EP-A-668267和WO-95/26954)。
已经公开了一些取代的Δ3-二氢呋喃-2-酮衍生物具有除草性能(参见DE-A-4014420)。用作起始物的季酮酸衍生物(例如3-(2-甲基-苯基)-4-羟基-5-(4-氟代苯基)-Δ3-二氢呋喃-2-酮)也公开于DE-A-4014420。此外,具有除草,杀螨,和杀虫性能的3-芳基-Δ3-二氢呋喃酮衍生物公开于EP-A-528156和EP-A-0647637。3-芳基-Δ3-二氢噻吩酮衍生物也已经公开(WO95/26345)。
具有除草,杀螨和杀虫性能的在苯环中被取代的苯基-吡喃酮衍生物公开于EP-A-588137。
具有除草,杀螨和杀虫作用的在苯环中被取代的5-苯基-1,3-噻嗪衍生物已经公开于WO94/14785。
但是,这些化合物的除草,杀螨和杀虫活性和/或作用范围,和植物耐受性,特别是农作物的耐受性并不总是充分的。
现已发现新的式(Ⅰ)化合物
其中A) V1代表氮原子和
V2代表CH或C-Z和
V3代表CY或B) V1代表CX和
V2代表氮原子和
V3代表CY或C) V1代表CX和
V2代表CH或C-Z和
V3代表氮原子,并且其中
W代表氢,氰基,硝基,卤素,烷基,链烯基,炔烃基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代链烯基氧基,或者在各种情况下任选被取代的苯基,苯氧基,苯硫基,苯基烷氧基或苯基烷硫基,
X代表氢,卤素,烷基,链烯基,炔烃基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代链烯基氧基,氰基,硝基,或者在各种情况下任选被取代的苯基,苯氧基,苯硫基,苯基烷氧基或苯基烷硫基,
Y代表氢,卤素,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,氰基或硝基,
Z代表卤素,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,羟基,氰基,硝基或者在各种情况下任选被取代的苯氧基,苯硫基,5-或6-元杂芳基氧基,5-或6-元杂芳基硫基,苯基烷基氧基或苯基烷硫基,或者
n代表1的情况下,Y和Z与它们所连的碳原子一起代表任选插入杂原子的任选被取代的环,或者
n代表1的情况下,W和Z与它们所连的紧邻的碳原子一起代表任选插入杂原子的任选被取代的环,
n代表0,1或在A)和C)的情况下,也代表2,当n=2时,取代基Z可是相同或不同的,
其中
A代表氢,或者代表烷基,链烯基,烷氧基烷基,多烷氧基烷基或烷基硫基烷基,这些基团任选被卤素取代,或者代表各种情况下饱和或不饱和的且任选被取代的环烷基或杂环基,或者代表芳基,芳基烷基,或杂芳基,这些基团任选被卤素,烷基,卤代烷基,烷氧基,卤代烷氧基,氰基或硝基取代,
B代表氢,烷基或烷氧基烷基,或者
A和B与它们所连的碳原子一起代表饱和的或不饱和的,任选被取代的碳环或杂环,
D代表氢或者任选被取代的烷基,链烯基,炔烃基,烷氧基烷基,多烷氧基烷基,烷基硫基烷基,饱和的或不饱和的环烷基,饱和的或不饱和的杂环基,芳基烷基,芳基,杂芳基烷基或杂芳基残基,或者
A和D与它们所连的原子一起代表各种情况下任选被取代的碳环或杂环,
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,
M代表氧或硫,
R1代表烷基,链烯基,烷氧基烷基,烷基硫基烷基或多烷氧基烷基,这些基团任选被卤素取代,或者代表环烷基或杂环基,这些基团任选被卤素,烷基或烷氧基取代,或者代表各种情况下任选被取代的苯基,苯基烷基,杂芳基,苯氧基烷基或杂芳基氧基烷基,
R2代表烷基,链烯基,烷氧基烷基或多烷氧基烷基,这些基团任选被卤素取代,或者代表各种情况下任选被取代的环烷基,苯基或苄基,
R3,R4,和R5各自独立地代表烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,链烯基硫基或环烷基硫基,这些基团任选被卤素取代,或者代表各种情况下任选被取代的苯基,苄基,苯氧基或苯硫基,
R6和R7各自独立地代表氢,或者代表烷基,环烷基,链烯基,烷氧基或烷氧基烷基,这些基团任选被卤素取代,或者代表各种情况下任选被取代的苯基或苄基,或者与它们所连的N原子一起形成任选包含氧原子或硫原子的任选被取代的环。
根据取代基的性质,式(Ⅰ)化合物也可以以几何和/或旋光异构体存在,或者由各种异构体混合物存在,其如果适当,可以用常规方法分离。本发明涉及纯的异构体和异构体混合物两者,涉及其制备方法和应用,涉及含有这些化合物的组合物。但是在下文中,为了简化起见,总是提到式(Ⅰ)化合物,但是应该理解这是指纯的化合物,或者如果适当,指含有各种量异构体化合物的混合物。
为了示出氮原子所占据的吡啶环的位置,当指结构式,以及母体或中间体时,下文将偶尔使用字母(A),(B)或(C)。
考虑到G组的各种定义(a),(b),(c),(d),(e),(f)和(g),如果Het代表第(1)组,则得到下面主要结构式(Ⅰ-1-a)至(Ⅰ-1-g)。其中A,B,E,L,M,W,V1,V2,V3,Z,n,R1,R2,R3,R4,R5,R6和R7具有上述定义。
考虑到G组的各种定义(a),(b),(c),(d),(e),(f)和(g),如果Het代表第(2)组,则得到下面主要结构式(Ⅰ-2-a)至(Ⅰ-2-g)。其中A,B,E,L,M,W,V1,V2,V3,Z,n,R1,R2,R3,R4,R5,R6和R7具有上述定义。
考虑到G组的各种定义(a),(b),(c),(d),(e),(f)和(g),如果Het代表第(3)组,则得到下面主要结构式(Ⅰ-3-a)至(Ⅰ-3-g)。其中A,B,E,L,M,W,V1,V2,V3,Z,n,R1,R2,R3,R4,R5,R6和R7具有上述定义。
式(Ⅰ-4)a和(Ⅰ-4)b化合物可以以混合物存在,但是也可以以其纯异构体存在。如果需要,式(Ⅰ-4)a和(Ⅰ-4)b化合物的混合物可以以本身已知的方法通过物理方法,例如通过色谱方法来分离。
为清楚起见,下文中每种情况下将只是提到一种异构体。如果适当,不排除化合物能以异构体混合物形式存在或者以其它异构体形式存在。
考虑到G组的各种定义(a),(b),(c),(d),(e),(f)和(g),如果Het代表第(4)组,则得到下面主要结构式(Ⅰ-4-a)至(Ⅰ-4-g)。 其中A,D,E,L,M,W,V1,V2,V3,Z,n,R1,R2,R3,R4,R5,R6和R7具有上述定义。
考虑到G组的各种定义(a),(b),(c),(d),(e),(f)和(g),如果Het代表第(5)组,则得到下面主要结构式(Ⅰ-5-a)至(Ⅰ-5-g)。 其中A,E,L,M,W,V1,V2,V3,Z,n,R1,R2,R3,R4,R5,R6和R7具有上述定义。
此外发现式(Ⅰ)新的化合物通过下述方法获得:(A)在稀释剂存在下和在碱的存在下,式(Ⅱ)化合物其中A,B,W,V1,V2,V3,n和Z具有上述定义,并且R8代表烷基(优选C1-C6-烷基)进行分子内缩合反应时,得到式(Ⅰ-1-a)化合物其中A,B,W,V1,V2,V3,n和Z具有上述定义。(B)此外发现,当在稀释剂存在下和在碱的存在下,式(Ⅲ)化合物其中A,B,W,V1,V2,V3,n,Z和R8具有上述定义,进行分子内缩合反应时,得到式(Ⅰ-2-a)化合物其中A,B,W,V1,V2,V3,n和Z具有上述定义。(C)而且发现,如果适当在稀释剂存在下和在酸存在下,式(Ⅳ)化合物其中A,B,W,V1,V2,V3,n,Z和R8具有上述定义,并且T代表氢,卤素,烷基(优选C1-C6-烷基)或烷氧基(优选C1-C8-烷氧基),进行分子内缩合反应时,得到式(Ⅰ-3-a)化合物其中A,B,W,V1,V2,V3,n和Z具有上述定义。(D)而且发现,如果适当在稀释剂存在下和如果适当在酸受体存在下,式(Ⅴ)化合物其中A和D具有上述定义,或者式(Ⅴa)的其甲硅烷基烯醇其中A和D具有上述定义,和R8’代表烷基(优选甲基),与式(Ⅵ)化合物反应时其中W,V1,V2,V3,n和Z具有上述定义和Hal代表卤素(优选氯或溴),得到式(Ⅰ-4-a)化合物其中A,D,W,V1,V2,V3,n和Z具有上述定义。(E)而且发现,如果适当在稀释剂存在下和如果适当在酸受体存在下,式(Ⅶ)化合物其中A具有上述定义,与式(Ⅵ)化合物反应时其中Hal,W,V1,V2,V3,n和Z具有上述定义,得到式(Ⅰ-5-a)化合物其中A,W,V1,V2,V3,n和Z具有上述定义。此外发现,(F)当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物进行下面的反应时,得到上述其中A,B,D,R1,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-b)至式(Ⅰ-5-b)化合物α)与式(Ⅷ)酰卤化物反应其中R1具有上述定义和Hal代表卤素(特别是氯或溴)或者β)如果适当在稀释剂存在和如果适当在酸结合剂存在下,与式(Ⅸ)酸酐反应
R1-CO-O-CO-R1 (Ⅸ)其中R1具有上述定义,(G)如果适当在稀释剂存在和如果适当在酸结合剂存在下,当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(Ⅹ)氯甲酸酯或氯甲酸硫酯反应时,
R2-M-CO-Cl (Ⅹ)其中R2和M具有上述定义,得到上述其中A,B,D,R2,W,M,V1,V2,V3,n和Z具有上述定义并且L代表氧的式(Ⅰ-1-c)至式(Ⅰ-5-c)化合物;(H)当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在下面各种情况下反应时,得到上述其中A,B,D,R2,W,M,V1,V2,V3,n和Z具有上述定义并且L代表硫的式(Ⅰ-1-c)至式(Ⅰ-5-c)化合物α)如果适当在稀释剂存在和如果适当在酸结合剂存在下,与式(Ⅺ)氯一硫甲酸酯或氯二硫甲酸酯反应其中M和R2具有上述定义,或者β)如果适当在稀释剂存在和如果适当在碱存在下,与二硫化碳反应并接着与式(Ⅻ)化合物反应
R2-Hal(Ⅻ)其中R2具有上述定义,Hal代表氯,溴或碘;(Ⅰ)如果适当在稀释剂存在和如果适当在酸结合剂存在下,当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅢ)磺酰氯反应时,
R3-SO2-Cl (ⅩⅢ)其中R3具有上述定义,得到上述其中A,B,D,R3,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-d)至式(Ⅰ-5-d)化合物。(J)如果适当在稀释剂存在和如果适当在酸结合剂存在下,当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅣ)磷化合物反应时,其中L,R4和R5具有上述定义且Hal代表卤素(特别是氯或溴),得到上述其中A,B,D,L,R4,R5,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-e)至式(Ⅰ-5-e)化合物;(K)如果适当在稀释剂存在下,当其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅤ)或(ⅩⅥ)的金属化合物或胺反应时,Me(OR10)t (ⅩⅤ)其中Me代表一价或二价金属(优选碱金属或碱土金属,例如锂,钠,钾,镁或钙),t代表数1或2,并且R10,R11,和R12各自独立地代表氢或者烷基(优选C1-C8-烷基),得到上述其中A,B,D,E,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-f)至式(Ⅰ-5-f)化合物;(L)当上述其中A,B,D,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在下面各种情况下反应时,得到上述其中A,B,D,L,R6,R7,W,V1,V2,V3,n和Z具有上述定义的式(Ⅰ-1-g)至式(Ⅰ-5-g)化合物α)如果适当在稀释剂存在下和如果适当在催化剂存在下,与式(ⅩⅦ)异氰酸酯或硫代异氰酸酯反应
而且发现新的式(Ⅰ)化合物作为杀虫剂优选作为杀昆虫剂,杀螨剂和除草剂具有非常好的活性,并且在一些情况下另外还具有非常好的植物耐受性,特别是农作物耐受性。
式(Ⅰ)或(Ⅰ-A),(Ⅰ-B)和(Ⅰ-C)分别提供了本发明化合物的一般定义。下面详细说明上下文提到的结构式中列出的优选取代基或基团范围:
W优选代表氢,硝基,氰基,卤素,C1-C6-烷基,C2-C6-链烯基,C2-C6-炔烃基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,或者代表苯基,苯氧基,苯硫基,苯基-C1-C4-烷氧基或苯基-C1-C4-烷硫基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基取代。
X优选代表氢,卤素,C1-C6-烷基,C2-C6-链烯基,C2-C6-炔烃基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,氰基,硝基,或者代表苯基,苯氧基,苯硫基,苯基-C1-C4-烷氧基或苯基-C1-C4-烷硫基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基取代。
Y优选代表氢,卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,氰基或硝基。
Z优选代表卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷硫基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,羟基,氰基,硝基,或者代表苯氧基,苯硫基,噻唑基氧基,吡啶基氧基,嘧啶基氧基,吡唑基氧基,苯基-C1-C4-烷氧基或苯基-C1-C4-烷硫基,其中各基团任选被卤素,C1-C4-烷基,C1-C4-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基取代,或者
Y和Z一起优选代表C3-C4-烷烃二基,C3-C4-烯烃二基或C4-烷烃二烯二基,其在各种情况下任选被卤素,C1-C6-烷基,C1-C6-烷氧基或C1-C4-卤代烷基取代,并且其中1-3个原子各自独立地可以任选被氧,硫,氮或羰基置换,各种情况下n代表1,或
W和Z一起优选代表C3-C4-烷烃二基,C3-C4-烯烃二基或C4-烷烃二烯二基,其在各种情况下任选被卤素,C1-C6-烷基,C1-C6-烷氧基或C1-C4-卤代烷基取代,并且其中1-3个原子各自独立地可以任选被氧,硫,氮或羰基置换,各种情况下n代表1,或
n优选代表0,1或2,如果n=2,则取代基Z可相同或不同。
A优选代表氢;或者代表C1-C12-烷基,C2-C8-链烯基,C1-C10-烷氧基-C1-C8-烷基,多C1-C8-烷氧基-C1-C8-烷基,或C1-C10-烷硫基-C1-C6-烷基,其中各基团任选被卤素取代;或者代表C3-C8-环烷基,其任选被卤素,C1-C6-烷基或C1-C6-烷氧基取代,并且其中1或2个不直接相邻的亚甲基基团任选被氧和/或硫置换;或者代表苯基,萘基,苯基-C1-C6-烷基,萘基-C1-C6-烷基或者具有5或6个环原子和1-3个选自氧,硫和氮的杂原子的杂芳基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,氰基或硝基取代。
B优选代表氢,C1-C12-烷基或C1-C8-烷氧基-C1-C6-烷基,或者
A,B和它们所连的碳原子优选代表C3-C10-环烷基或C5-C10-环烯基,其中各基团中一个亚甲基基团任选被氧或硫置换,并且其任选被C1-C8-烷基,C3-C10-环烷基,C1-C8-卤代烷基,C1-C8-烷氧基,C1-C8-烷硫基,卤素或苯基取代,或者
A,B和它们所连的碳原子优选代表C5-C6-环烷基,其被任选含有一个或两个氧和/或硫原子的亚烷二基基团或者被亚烷基二氧基基团或者被亚烷基二硫基基团取代,该基团与它们所连的碳原子形成又一个5-元至8元环,或者
A,B和它们所连的碳原子优选代表C3-C8-环烷基或C5-C8-环烯基,其中两个碳原子通过C3-C6-烷烃二基,C3-C6-烯烃二基或C4-C6-烷烃二烯二基连接,这些连接基团任选被C1-C6-烷基,C1-C6-烷氧基或卤素取代,并且其中各基团中的一个亚甲基任选被氧或硫置换。
D优选代表氢;或者代表C1-C12-烷基,C3-C8-链烯基,C3-C8-炔烃基,C1-C10-烷氧基-C2-C8-烷基,多-C1-C8-烷氧基-C2-C8-烷基,或C1-C10-烷硫基-C2-C8-烷基,其中各基团任选被卤素取代;或者代表C3-C8-环烷基,其任选被卤素,C1-C4-烷基,C1-C4-烷氧基或C1-C4-卤代烷基取代,并且其中1或2个不直接相邻的亚甲基基团被氧和/或硫置换;或者代表苯基,具有5或6个环原子和1或2个选自氧,硫和氮的杂原子的杂芳基,苯基-C1-C6-烷基或具有5或6个环原子和1或2个选自氧,硫和氮的杂原子的杂芳基-C1-C6-烷基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-卤代烷基,C1-C6-烷氧基,C1-C6-卤代烷氧基,氰基或硝基取代。
A和D一起优选代表C3-C6-烷烃二基,C3-C6-烯烃二基,或C4-C6-烷烃二烯二基基团,其中各基团中的一个亚甲基基团任选被氧或硫置换,并且其中各基团任选被卤素或者被任选被卤素取代的C1-C10-烷基,C1-C6-烷氧基,C1-C6-烷硫基,C3-C7-环烷基,苯基或苄基氧基取代,或者被又一个C3-C6-烷烃二基,C3-C6-烯烃二基或C4-C6-烷烃二烯二基基团取代,形成稠合的环,并且其中各基团中的一个亚甲基基团任选被氧或硫置换,并且其任选被C1-C6-烷基取代,或者
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,和
M代表氧或硫。
R1优选代表C1-C20-烷基,C2-C20-链烯基,C1-C8-烷氧基-C1-C8-烷基,C1-C8-烷基硫基-C1-C8-烷基或多-C1-C8-烷氧基-C1-C8-烷基,其中各基团任选被卤素取代,或者代表C3-C8-环烷基,其任选被卤素,C1-C6-烷基或C1-C6-烷氧基取代并且其中一个或两个不直接相邻的亚甲基基团任选被氧和/或硫置换,
或者代表任选被卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基,C1-C6-烷硫基或C1-C6-烷基磺酰基取代的苯基,
或者代表任选被卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基,C1-C6-卤代烷氧基取代的苯基-C1-C6-烷基,
或者代表任选被卤素或C1-C6-烷基取代的具有一个或两个选自氧,硫或氮的杂原子的5-元或6-元杂芳基,
或者代表任选被卤素或C1-C6-烷基取代的苯氧基-C1-C6-烷基,
或者代表任选被卤素,氨基或C1-C6-烷基取代的具有一个或两个选自氧,硫和氮的杂原子的5-元或6-元杂芳氧基-C1-C6-烷基,
R2优选代表C1-C20-烷基,C2-C20-链烯基,C1-C8-烷氧基-C2-C8-烷基或多-C1-C8-烷氧基-C2-C8-烷基,其中各基团任选被卤素取代,
或者代表任选被卤素,C1-C6-烷基或C1-C6-烷氧基取代的C3-C8-环烷基,
或者代表苯基或苄基,其中各基团任选被卤素,氰基,硝基,C1-C6-烷基,C1-C6-烷氧基,C1-C6-卤代烷基或C1-C6-卤代烷氧基取代。
R3优选代表任选被卤素取代的C1-C8-烷基,或者代表苯基或苄基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,氰基或硝基取代。
R4和R5各自独立地优选代表C1-C8-烷基,C1-C8-烷氧基,C1-C8-烷基氨基,二(C1-C8-烷基)氨基,C1-C8-烷硫基或C3-C8-链烯基硫基,其中各基团任选被卤素取代,或者代表苯基,苯氧基或苯硫基,其中各基团任选被卤素,氰基,硝基,C1-C4-烷氧基,C1-C4-卤代烷氧基,C1-C4-烷硫基,C1-C4-卤代烷硫基,C1-C4-烷基或C1-C4-卤代烷基取代。
R6和R7各自独立地优选代表氢,或者代表C1-C8-烷基,C3-C8-环烷基,C3-C8-链烯基,C1-C8-烷氧基或C1-C8-烷氧基-C2-C8-烷基,其中各基团任选被卤素取代,或者代表苯基或苄基,其中各基团任选被卤素,C1-C8-烷基,C1-C8-卤代烷基或C1-C8-烷氧基取代,或者一起代表其中一个亚甲基任选被氧或硫置换并且任选被C1-C6-烷基取代的C3-C6-亚烷基。
R13优选代表氢;或者代表C1-C8-烷基或C1-C8-烷氧基,其中各基团任选被卤素取代;或者代表其中一个亚甲基任选被氧或硫置换并且任选被卤素,C1-C4-烷基或C1-C4-烷氧基取代的C3-C8-环烷基;或者代表苯基,苯基-C1-C4-烷基或苯基-C1-C4-烷氧基,其中各基团任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,氰基或硝基取代。
R14优选代表氢或C1-C8-烷基,或
R13和R14一起优选代表C4-C6-烷烃二基。
R15和R16是相同或不同的,并且优选代表C1-C6-烷基,或
R15和R16一起优选代表C2-C4-烷烃二基,其任选被C1-C6-烷基或者被任选被卤素,C1-C4-烷基,C1-C4-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基取代的苯基取代。
R17和R18各自独立地优选代表氢,或者代表任选被卤素取代的C1-C8-烷基,或者代表任选被卤素,C1-C6-烷基,C1-C6-烷氧基,C1-C4-卤代烷基,C1-C4-卤代烷氧基,硝基或氰基取代的苯基,或者
R17和R18与它们所连的碳原子一起代表其中一个亚甲基任选被氧或硫置换并且任选被C1-C4-烷基取代的C5-C7-环烷基。
R19和R20各自独立地优选代表C1-C10-烷基,C2-C10-链烯基,C1-C10-烷氧基,C1-C10-烷基氨基,C3-C10-链烯基氨基,二(C1-C10-烷基)氨基或二(C3-C10-链烯基)氨基。
W特别优选地代表氢,氰基,硝基,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,或者代表苯基,苯氧基,苄基或苄基氧基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,硝基或氰基取代。
X特别优选地代表氢,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,氰基,硝基,或者代表苯基,苯氧基,苄基或苄基氧基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,硝基或氰基取代。
Y特别优选地代表氢,氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,氰基或硝基。
Z特别优选地氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,羟基,氰基,硝基,或者代表苯氧基或苄基氧基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,硝基或氰基取代。
n特别优选地代表0或1。
Het特别优选地代表下面基团之一:
A特别优选地代表氢;或者代表C1-C10-烷基,C2-C6-链烯基,C1-C8-烷氧基-C1-C6-烷基,多-C1-C6-烷氧基-C1-C6-烷基或C1-C8-烷硫基-C1-C6-烷基,其中各基团任选被氟或氯取代;或者代表C3-C8-环烷基,其中1或2个不直接相邻的亚甲基基团任选被氧和/或硫置换,并且其任选被氟,氯,C1-C4-烷基或C1-C4-烷氧基取代;或者代表苯基,呋喃基,吡啶基,咪唑基,三唑基,吡唑基,吲哚基,噻唑基,噻吩基或苯基-C1-C4-烷基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,氰基或硝基取代。
B特别优选地代表氢,C1-C10-烷基或C1-C6-烷氧基-C1-C4-烷基,或者
A,B和它们所连的碳原子特别优选地代表C3-C8-环烷基或C5-C8-环烯烃基,其中各基团中一个亚甲基基团任选被氧或硫置换,并且其任选被C1-C6-烷基或C1-C6-烷氧基取代,或者
A,B和它们所连的碳原子特别优选地代表C5-C6-环烷基,其被任选含有一个或两个氧或硫原子的亚烷基二基基团或者被亚烷基二氧基基团或者被亚烷基二硫基基团取代,该基团与它们所连的碳原子形成又一个5-元至7元环,或者
A,B和它们所连的碳原子特别优选地代表C3-C6-环烷基或C5-C6-环烯烃基,其中两个碳原子通过C3-C5-烷烃二基,C3-C5-烯烃二基或丁二烯二基连接,其中这些连接基团中的一个亚甲基任选被氧或硫置换并且其任选被C1-C4-烷基或C1-C4-烷氧基取代。
D特别优选地代表氢,或者代表C1-C10-烷基,C3-C6-链烯基,C3-C6-炔烃基,C1-C8-烷氧基-C2-C6-烷基,多-C1-C6-烷氧基-C2-C6-烷基或C1-C8-烷硫基-C2-C6-烷基,其中各基团任选被氟或氯取代;或者代表C3-C7-环烷基,其任选被氟,氯,C1-C4-烷基,C1-C4-烷氧基或C1-C2-卤代烷基取代,并且其中1或2个不直接相邻的亚甲基基团任选被氧和/或硫置换;或者代表苯基,呋喃基,咪唑基,吡啶基,噻唑基,吡唑基,嘧啶基,吡咯基,噻吩基,三唑基或苯基-C1-C4-烷基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,氰基或硝基取代,或者
A和D一起特别优选地代表C3-C5-烷烃二基或C3-C5-烯烃二基,其中各基团中的一个亚甲基基团任选被氧或硫置换,并且其任选被氟,氯或者被任选被氟或氯取代的C1-C6-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C3-C6-环烷基,苯基或苄基氧基取代,或者
其中
E代表金属离子等价物或铵离子,
L代表氧或硫和
M代表氧或硫。
R1特别优选地代表C1-C16-烷基,C2-C16-链烯基,C1-C6-烷氧基-C1-C6-烷基,C1-C6-烷基硫基-C1-C6-烷基或多-C1-C6-烷氧基-C1-C6-烷基,其中各基团任选被氟或氯取代;或者代表C3-C7-环烷基,其中一个或两个不直接相邻的亚甲基基团任选被氧和/或硫置换,并且其任选被氟,氯,C1-C5-烷基或C1-C5-烷氧基取代,
或者代表任选被氟,氯,溴,氰基,硝基,C1-C4-烷基,C1-C4-烷氧基,C1-C3-卤代烷基,C1-C3-卤代烷氧基,C1-C4-烷硫基或C1-C4-烷基磺酰基取代的苯基,
或者代表任选被氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C3-卤代烷基或C1-C3-卤代烷氧基取代的苯基-C1-C4-烷基,
或者代表吡唑基,噻唑基,吡啶基,嘧啶基,呋喃基或噻吩基,其中各基团任选被氟,氯,溴或C1-C4-烷基取代,
或者代表任选被氟,氯,溴或C1-C4-烷基取代的苯氧基-C1-C5-烷基,
或者代表吡啶基氧基-C1-C5-烷基,嘧啶基氧基-C1-C5-烷基或噻唑基氧基-C1-C5-烷基,其中各基团任选被氟,氯,溴,氨基或C1-C4-烷基取代,
R2特别优选地代表C1-C16-烷基,C2-C16-链烯基,C1-C6-烷氧基-C2-C6-烷基或多-C1-C6-烷氧基-C2-C6-烷基,其中各基团任选被氟或氯取代,
或者代表任选被氟,氯,C1-C4-烷基或C1-C4-烷氧基取代的C3-C7-环烷基,
或者代表苯基或苄基,其中各基团任选被氟,氯,溴,氰基,硝基,C1-C4-烷基,C1-C3-烷氧基,C1-C3-卤代烷基或C1-C3-卤代烷氧基取代。
R3特别优选地代表任选被氟或氯取代的C1-C6-烷基,或者代表苯基或苄基,其中各基团任选被氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,氰基或硝基取代。
R4和R5各自独立地特别优选地代表C1-C6-烷基,C1-C6-烷氧基,C1-C6-烷基氨基,二(C1-C6-烷基)氨基,C1-C6-烷硫基或C3-C4-链烯基硫基,其中各基团任选被氟或氯取代;或者代表苯基,苯氧基或苯硫基,其中各基团任选被氟,氯,溴,氰基,硝基,C1-C3-烷氧基,C1-C3-卤代烷氧基,C1-C3-烷硫基,C1-C3-卤代烷硫基,C1-C3-烷基或C1-C3-卤代烷基取代。
R6和R7各自独立地特别优选地代表氢;或者代表C1-C6-烷基,C3-C6-环烷基,C3-C6-链烯基,C1-C6-烷氧基或C1-C6-烷氧基-C2-C6-烷基,其中各基团任选被氟或氯取代;或者代表苯基或苄基,其中各基团任选被氟,氯,溴,C1-C5-烷基,C1-C5-卤代烷基或C1-C5-烷氧基取代;或者一起代表任选被C1-C4-烷基取代的并且其中一个亚甲基任选被氧或硫置换的C3-C6-亚烷基。
R13特别优选地代表氢;或者代表C1-C6-烷基或C1-C6-烷氧基,其中各基团任选被氟或氯取代;或者代表其中一个亚甲基任选被氧或硫置换并且其任选被氟,C1-C2-烷基或C1-C2-烷氧基取代的C3-C7-环烷基;或者代表苯基,苯基-C1-C3-烷基或苯基-C1-C2-烷氧基,其中各基团任选被氟,氯,溴,C1-C5-烷基,C1-C5-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,氰基或硝基取代。
R14特别优选地代表氢或C1-C6-烷基,或
R13和R14一起特别优选地代表C4-C6-烷烃二基。
R15和R16是相同或不同的,并且特别优选地代表C1-C4-烷基,或
R15和R16一起特别优选代表C2-C3-烷烃二基,其任选被C1-C4-烷基或者被任选被氟,氯,溴,C1-C2-烷基,C1-C2-烷氧基,C1-C2-卤代烷基,C1-C2-卤代烷氧基,硝基或氰基取代的苯基取代。
W非常特别地优选代表氢,氟,氯,溴,甲基,乙基,甲氧基,乙氧基或三氟甲基。
X非常特别地优选代表氢,氟,氯,溴,甲基,乙基,甲氧基,乙氧基或三氟甲基。
Y非常特别地优选代表氢,氟,氯,溴,甲基,乙基,甲氧基,乙氧基或三氟甲基。
Z非常特别地优选代表氟,氯,溴,甲基,乙基,甲氧基,乙氧基或三氟甲基。
n非常特别地优选代表0或1。
A非常特别地优选代表氢;或者代表C1-C8-烷基,C2-C4-链烯基,C1-C6-烷氧基-C1-C4-烷基,多-C1-C4-烷氧基-C1-C4-烷基或C1-C6-烷硫基-C1-C4-烷基,其中各基团任选被氟或氯取代;或者代表C3-C6-环烷基,其中1或2个不直接相邻的亚甲基基团任选被氧和/或硫置换,并且其任选被氟,氯,甲基或甲氧基取代;或者代表苯基,吡啶基或苄基,其中各基团任选被氟,氯,溴,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,三氟甲基或三氟甲氧基取代。
B非常特别地优选代表氢,C1-C8-烷基或C1-C4-烷氧基-C1-C2-烷基,或者
A,B和它们所连的碳原子非常特别地优选代表C3-C8-环烷基或C5-C8-环烯烃基,其中各基团中-个亚甲基基团任选被氧或硫置换,并且其任选被甲基,乙基,正丙基,异丙基,丁基,异丁基,仲丁基,叔丁基,甲氧基,乙氧基,正丙氧基,异丙氧基。丁氧基,异丁氧基,仲丁氧基或叔丁氧基取代,或者
A,B和它们所连的碳原子非常特别地优选代表C5-C6-环烷基,其被任选含有氧或硫原子的亚烷基二基基团或者被亚烷基二氧基基团取代,该基团与它们所连的碳原子形成又一个5-元至6-元环,或者
A,B和它们所连的碳原子非常特别地优选代表C3-C6-环烷基或C5-C6-环烯烃基,其中两个碳原子通过C3-C4-烷烃二基,C3-C4-烯烃二基或丁二烯二基连接,其中这些连接基团中的一个亚甲基任选被氧或硫置换。
D非常特别地优选代表氢;或者代表C1-C8-烷基,C3-C4-链烯基,C3-C4-炔烃基,C1-C6-烷氧基-C2-C4-烷基,多-C1-C4-烷氧基-C2-C4-烷基,C1-C4-烷硫基-C2-C4-烷基或C3-C6-环烷基,其中1或2个不直接相邻的亚甲基基团任选被氧和/或硫置换,并且其中各基团任选被氟或氯取代;或者代表苯基,呋喃基,吡啶基,噻吩基或苄基,其中各基团任选被氟,氯,溴,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,三氟甲基,三氟甲氧基,氰基或硝基取代,或者
A和D一起非常特别地优选代表C3-C5-烷烃二基或C3-C5-烯烃二基,其中各基团中的一个亚甲基基团任选被氧或硫置换,并且其任选被氟,氯,甲基或甲氧基取代。
G非常特别地优选代表氢(a)或下面的基团之一其中E代表金属离子等价物或铵离子,L代表氧或硫和
M代表氧或硫。
R1非常特别地优选代表C1-C14-烷基,C2-C14-链烯基,C1-C4-烷氧基-C1-C6-烷基,C1-C4-烷基硫基-C1-C6-烷基或多-C1-C4-烷氧基-C1-C4-烷基,其中各基团任选被氟或氯取代;或者代表C3-C6-环烷基,其中一个或两个不直接相邻的亚甲基基团任选被氧和/或硫置换,并且其任选被氟,氯,甲基,乙基,正丙基,异丙基,正丁基,异丁基,叔丁基,甲氧基,乙氧基,正丙氧基或异丙氧基取代,
或者代表任选被氟,氯,溴,氰基,硝基,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,三氟甲基,三氟甲氧基,甲基硫基,乙基硫基,甲基磺酰基或乙基磺酰基取代的苯基,
或者代表任选被氟,氯,溴,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,三氟甲基或三氟甲氧基取代的苄基,
或者代表呋喃基,噻吩基或吡啶基,其中各基团任选被氟,氯,溴,甲基或乙基取代,
或者代表任选被氟,氯,溴,甲基或乙基取代的苯氧基-C1-C4-烷基,
或者代表吡啶基氧基-C1-C4-烷基,嘧啶基氧基-C1-C4-烷基或噻唑基氧基-C1-C4-烷基,其中各基团任选被氟,氯,氨基,甲基或乙基取代。
R2非常特别地优选代表C1-C14-烷基,C2-C14-链烯基,C1-C4-烷氧基-C2-C6-烷基或多-C1-C4-烷氧基-C2-C6-烷基,其中各基团任选被氟或氯取代,
或者代表任选被氟,氯,甲基,乙基,正丙基,异丙基或甲氧基取代的C3-C6-环烷基,
或者代表苯基或苄基,其中各基团任选被氟,氯,溴,氰基,硝基,甲基,乙基,正丙基,异丙基,甲氧基,乙氧基,三氟甲基或三氟甲氧基取代,
R3非常特别地优选代表甲基,乙基,丙基,异丙基,正丁基,叔丁基,其中各基团任选被氟或氯取代;或者代表苯基或苄基,其中各基团任选被氟,氯,溴,甲基,乙基,异丙基,叔丁基,甲氧基,乙氧基,异丙氧基,三氟甲基,三氟甲氧基,氰基或硝基取代。
R4和R5各自独立地非常特别地优选代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷基氨基,二(C1-C4-烷基)氨基或C1-C4-烷硫基,其中各基团任选被氟或氯取代;或者代表苯基,苯氧基或苯硫基,其中各基团任选被氟,氯,溴,氰基,硝基,甲基,甲氧基,三氟甲基或三氟甲氧基取代。
R6和R7各自独立地非常特别地优选代表氢;或者代表C1-C4-烷基,C3-C6-环烷基,C3-C4-链烯基,C1-C4-烷氧基或C1-C4-烷氧基-C2-C4-烷基,其中各基团任选被氟或氯取代;或者代表苯基或苄基,其中各基团任选被氟,氯,溴,甲基,甲氧基或三氟甲基取代;或者一起代表其中一个亚甲基任选被氧或硫置换并且任选被甲基或乙基取代的C5-C6-亚烷基。
该规则适用于当这些碳原子是直接相邻时W和Z与它们所连的碳原子一起只形成一个环。
上述一般或优选范围中基团或详细说明的定义可以根据需要相互组合,也就是说各范围和优选范围之间的组合也是可能的。其适用于终产物,并且类似适用于母体和中间体。
优选的本发明是其中有上述作为优选的定义的组合的那些式(Ⅰ)化合物。
特别优选的本发明是其中有上述作为特别优选的定义的组合的那些式(Ⅰ)化合物。
非常特别优选的本发明是其中有上述作为非常特别优选的定义的组合的那些式(Ⅰ)化合物。
特别优选的一组式(Ⅰ)化合物是通过其中V1是氮的那些化合物形成的。
进一步特别优选的一组式(Ⅰ)化合物是通过其中V2是氮的那些化合物形成的。
进一步特别优选的一组式(Ⅰ)化合物是通过其中V3是氮的那些化合物形成的。
此外,特别优选的式(Ⅰ)化合物是其中Het代表下面基团的那些化合物
只要有可能,饱和的或不饱和的烃基,例如烷基或链烯基,在各种情况下可以是直链或支链的,也可以与杂原子结合,例如在烷氧基中。
任选被取代的基团可以是一取代的或多取代的,在多取代的情况下取代基可以是相同或不同的。
除了制备实施例中提到的化合物外,可以分别提到下面的式(Ⅰ-1-a)化合物:
表1 W=CH3;V1=CCH3;V2=N;V3=CH;Zn=H
表2:A和B具有和表1相同的意义,并且
W=CH3;V1=CCl;V2=N;V3=CH;Zn=H表3:A和B具有和表1相同的意义,并且
W=CH3;V1=CCH3;V2=N;V3=CCH3;Zn=H表4:A和B具有和表1相同的意义,并且
W=H;V1=CCl;V2=N;V3=CH;Zn=H表5:A和B具有和表1相同的意义,并且
W=CH3;V1=N;V2=CH;V3=CCH3;Zn=H表6:A和B具有和表1相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCl;Zn=H表7:A和B具有和表1相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCH3;Zn=H表8:A和B具有和表1相同的意义,并且
W=CH3;V1=N;V2=CH;V3=CCl;Zn=H表9:A和B具有和表1相同的意义,并且
W=CH3;V1=CH;V2=CH;V3=N;Zn=H表10:A和B具有和表1相同的意义,并且
W=H;V1=C-Cl;V2=N;V3=C-Cl;Zn=H表11:A和B具有和表1相同的意义,并且
W=Cl;V1=CH;V2=N;V3=C-Cl;Zn=H
表12 W=CH3;V1=CCH3;V2=N;V3=CH;Zn=H
A | B |
CH3 | H |
C2H5 | H |
C3H7 | H |
i-C3H7 | H |
C4H9 | H |
i-C4H9 | H |
s-C4H9 | H |
t-C4H9 | H |
CH3 | CH3 |
C2H5 | CH3 |
C3H7 | CH3 |
i-C3H7 | CH3 |
C4H9 | CH3 |
i-C4H9 | CH3 |
s-C4H9 | CH3 |
t-C4H9 | CH3 |
C2H5 | C2H5 |
C3H7 | C3H7 |
表12(续)
表13:A和B具有和表12相同的意义,并且
W=CH3;V1=CCl;V2=N;V3=CH;Zn=H表14:A和B具有和表12相同的意义,并且
W=CH3;V1=CCH3;V2=N;V3=CCH3;Zn=H表15:A和B具有和表12相同的意义,并且
W=H;V1=CCl;V2=N;V3=CH;Zn=H表16:A和B具有和表12相同的意义,并且
W=CH3;V1=N;V2=CH;V3=CCH3;Zn=H表17:A和B具有和表12相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCl;Zn=H表18:A和B具有和表12相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCH3;Zn=H表19:A和B具有和表12相同的意义,并且
W=CH3;V1=N;V2=CH;V3=CCl;Zn=H表20:A和B具有和表12相同的意义,并且
W=CH3;V1=CH;V2=CH;V3=N;Zn=H表21:A和B具有和表12相同的意义,并且
W=H;V1=C-Cl;V2=N;V3=C-Cl;Zn=H表22:A和B具有和表12相同的意义,并且
W=Cl;V1=CH;V2=N;V3=C-Cl;Zn=H
除了制备实施例中提到的化合物外,可以分别提到下面的式(Ⅰ-3-a)化合物:
表23 W=CH3;V1=CCH3;V2=N;V3=CH;Zn=H
A | B |
CH3 | H |
C2H5 | H |
C3H7 | H |
i-C3H7 | H |
C4H9 | H |
i-C4H9 | H |
s-C4H9 | H |
t-C4H9 | H |
CH3 | CH3 |
C2H5 | CH3 |
C3H7 | CH3 |
i-C3H7 | CH3 |
C4H9 | CH3 |
i-C4H9 | CH3 |
s-C4H9 | CH3 |
t-C4H9 | CH3 |
C2H5 | C2H5 |
C3H7 | C3H7 |
表23(续)
表24:A和B具有和表23相同的意义,并且
W=CH3;V1=CCl;V2=N;V3=CH;Zn=H表25:A和B具有和表23相同的意义,并且
W=CH3;V1=CCH3;V2=N;V3=CH3;Zn=H表26:A和B具有和表23相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCl;Zn=H表27:A和B具有和表23相同的意义,并且
W=CH3;V1=CH;V2=CH;V3=N;Zn=H表28:A和B具有和表23相同的意义,并且
W=H;V1=C-Cl;V2=N;V3=C-Cl;Zn=H表29:A和B具有和表23相同的意义,并且
W=Cl;V1=CH;V2=N;V3=C-Cl;Zn=H
表30(续)
表30(续)
A | D |
CH3 | C5H9 |
CH3 | C3H5 |
H | C3H4Cl |
(CH2)3 | |
(CH2)4 | |
C(CH3)2OC(CH3)2 |
表31:A和D具有和表30相同的意义,并且
W=CH3;V1=CCl;V2=N;V3=CH;Zn=H表32:A和D具有和表30相同的意义,并且
W=CH3;V1=CCH3;V2=N;V3=CCH3;Zn=H表33:A和D具有和表30相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCl;Zn=H表34:A和D具有和表30相同的意义,并且
W=CH3;V1=CH;V2=CH;V3=N;Zn=H
除了制备实施例中提到的化合物外,可以分别提到下面的式(Ⅰ-5-a)化合物:
表36:A具有和表35相同的意义,并且
W=CH3;V1=CCl;V2=N;V3=CH;Zn=H表37:A具有和表35相同的意义,并且
W=CH3;V1=CCH3;V2=N;V3=CCH3;Zn=H表38:A具有和表35相同的意义,并且
W=Cl;V1=N;V2=CH;V3=CCl;Zn=H表39:A具有和表35相同的意义,并且
W=CH3;V1=CH;V2=CH;V3=N;Zn=H
如果根据方法(F)(变化方法β),用3-[2-(3-氯代)-吡啶基]-4-羟基-5-苯基-Δ3-二氢呋喃-2-酮和乙酸酐为起始物,则根据本发明方法的过程可以用下面的反应式代表:
如果根据方法(H)(变化方法β),用5-[4-(2-氯代-3,5-二甲基)-吡啶基]-6-羟基-2-(4-氯代苯基)-噻嗪-4-酮,二硫化碳和碘甲烷为起始物,则根据本发明方法的过程可以用下面的反应式代表:
如果根据方法(J),用2-[4-(3-氯代-5-甲基)-吡啶基]-4-羟基-5-甲基-6-(2-吡啶基)-吡喃酮和甲烷硫代磷酸酰氯2,2,2-三氟乙酯为起始物,则根据本发明方法的过程可以用下面的反应式代表:
如果根据方法(K),用3-[3-(2,6-二氯)-4-甲基吡啶基]-5-环丙基-5-甲基-吡咯烷-2,4-二酮和氢氧化钠为起始物,则根据本发明方法的过程可以用下面的反应式代表:
如果根据方法(L)(变化方法α),用3-[3-(2-氯-6-溴-5-甲基)-吡啶基]-4-羟基-5,5-四亚甲基-Δ3-二氢-呋喃-2-酮和异氰酸乙酯为起始物,则根据本发明方法的过程可以用下面的反应式代表:
如果根据方法(L)(变化方法β),用3-[4-(3-氯-5-甲基)-吡啶基]-5-甲基-吡咯烷-2,4-二酮和二甲基氨基甲酰氯为起始物,则根据本发明方法的过程可以用下面的反应式代表:式(Ⅱ)化合物是新的其中A,B,W,X,Z,V1,V2,V3,n和R8具有上述定义,其在本发明方法(A)中需要作为起始物。例如,当式(ⅩⅨ)氨基酸衍生物其中A,B和R8具有上述定义,被式(ⅩⅩ)的取代的吡啶基乙酰卤酰化时其中W,V1,V2,V3,n和Z具有上述定义并且Hal代表氯或溴,(化学综述(Chem.Reviews)52,237-416(1953);Bhattacharya,印度化学杂志(Indian J.Chem.)6.341-5,1968),或者当式(ⅩⅪ)酰基氨基酸其中A,B,W,V1,V2,V3,n和Z具有上述定义,被酯化时(Chem.Ind.(伦敦)1568(1968))得到式(Ⅱ)酰基氨基酸酯。式(ⅩⅪ)化合物是新的其中A,B,W,V1,V2,V3,n和Z具有上述定义。当式(ⅩⅫ)氨基酸其中A和B具有上述定义,被式(ⅩⅩ)取代的吡啶基乙酰卤通过Schotten-Baumann方法(Organikum,VEB Deutscher Verlag der Wissenschaften,柏林1977,p.505)酰化时其中W,V1,V2,V3,n和Z具有上述定义并且Hal代表氯或溴,得到式(ⅩⅪ)化合物。
一些式(ⅩⅩ)化合物是新的。其可以通过已知的方法制备。
例如,如果适当在稀释剂存在下(例如任选被氯化的脂肪烃或芳香烃,例如甲苯或二氯甲烷),在-20℃至150℃,优选-10℃至100℃的温度下,式(ⅩⅩ)化合物通过使式(ⅩⅩⅢ)的取代的吡啶基乙酸用卤化剂(例如亚硫酰氯,亚硫酰溴,草酰氯,光气,三氯化磷,三溴化磷或五氯化磷)卤化得到,其中W,V1,V2,V3,n和Z具有上述定义。
一些式(ⅩⅩⅢ)化合物是新的。其可以通过文献中已知的方法制备(参见,例如Organikum,第15版,p.533,VEB Deutscher Verlag derWissenschaften,柏林1977和制备实施例)。式(ⅩⅩⅢ)化合物例如通过在0℃和150℃之间的温度下,优选20℃和100℃之间,在酸(例如无机酸例如盐酸)或碱(例如碱金属氢氧化物例如氢氧化钠或氢氧化钾)存在下,和如果适当,在稀释剂(例如含水的醇例如甲醇或乙醇)存在下,水解式(ⅩⅩⅣ)的取代的吡啶基乙酸酯而获得其中W,V1,V2,V3,n,Z和R8具有上述定义。
一些式(ⅩⅩⅣ)化合物是新的。其可以通过原则上已知的方法制备。
例如式(ⅩⅩⅣ)化合物通过在稀释剂(例如从烷氧化物衍生的醇)存在下,在0℃和150℃之间的温度下,优选20℃和120℃之间,使式(ⅩⅩⅤ)的取代的1,1,1-三氯-2-吡啶基乙烷首先与烷氧化物(例如碱金属烷氧化物例如甲醇钠或乙醇钠)反应,并且接着在-20℃和150℃之间的温度下,优选0℃和100℃之间与酸(优选无机酸例如硫酸)反应而获得(参见DE 3314249),其中W,V1,V2,V3,n和Z具有上述定义。
式(ⅩⅩⅤ)化合物是新的。其可以通过原则上已知的方法制备。
例如,当在氯化铜(Ⅱ)存在下,和如果适当,在稀释剂(例如脂肪族腈例如乙腈)存在下,在-20℃至80℃,优选0℃至60℃的温度下,式(ⅩⅩⅥ)的氨基吡啶与二氯乙烯(CH2=CCl2)在式(ⅩⅩⅦ)亚硝酸烷基酯存在下反应获得式(ⅩⅩⅤ)化合物其中W,V1,V2,V3,n和Z具有上述定义,R21-ONO (ⅩⅩⅦ)其中R21代表烷基,优选C1-C6-烷基。
式(ⅩⅩⅥ)和(ⅩⅩⅦ)化合物是有机化学已知化合物。氯化铜(Ⅱ)和二氯乙烯很久以前就是已知的并且可以购得。
式(ⅩⅨ)和(ⅩⅫ)化合物在某些情况下是已知的和/或可以通过已知的方法合成(参见例如Compagnon,Ann.Chim.(巴黎)[14]5,pp.11-12,23-27(1970))。
其中A和B形成一个环的式(ⅩⅫa)的取代的环氨基羧酸一般通过Bucherer-Bergs合成或者通过Strecher合成而获得,其中每种情况下以不同的异构体形式获得。因此,Bucherer-Bergs合成的条件优先获得其中R基和羧基是在平伏位置的异构体(为简化起见下文称为β),而Strecher合成的条件优先获得其中氨基和R基是在平伏位置的异构体(为简化起见下文称为α)Bucherer-Bergs合成 Strecker合成(β异构体) (α异构体)(L.Munday,J.Chem.Soc 4372(1961);J.T.Eward,C.Jitrangeri,Can.J.Chem.53,3339(1975))
此外,当式(ⅩⅩⅧ)的氨基腈其中A和B具有上述定义,和式(ⅩⅩ)的取代的吡啶基乙酰卤反应其中W,V1,V2,V3,n,Z和Hal具有上述定义,得到式(ⅩⅩⅨ)化合物其中A,B,W,V1,V2,V3,n和Z具有上述定义,接着使这些化合物进行酸醇解,来制备在上面方法(A)中使用的式(Ⅱ)起始物其中A,B,W,V1,V2,V3,n,Z和R8具有上述定义。式(ⅩⅩⅨ)化合物也是新的。在本发明方法(B)中需要用作起始物的式(Ⅲ)化合物是新的其中A,B,W,V1,V2,V3,n,Z和R8具有上述定义。
其通过原则上已知的方法以简单的方式制备。
例如,当用式(ⅩⅩ)的取代的吡啶基酰卤酰化式(ⅩⅩⅩ)的2-羟基羧酸酯时,得到式(Ⅲ)化合物其中A,B和R8具有上述定义,其中W,V1,V2,V3,n,Z和Hal具有上述定义(化学综述(Chem.Reviews)52,237-416(1953))。
式(ⅩⅩⅪ)化合物可以购得或者可以通过已知的方法以简单的方式制备。
其通过原则上已知的方法以简单的方式制备。
例如,当在强碱存在下,用式(ⅩⅩⅫ)的2-苄基硫基羧酸卤化物酰化式(ⅩⅩⅣ)的取代的吡啶基乙酸酯时,得到式(Ⅳ)化合物其中W,V1,V2,V3,n,R8和Z具有上述定义,其中A,B和T具有上述定义,并且Hal 代表卤素(特别是氯或溴)(参见,例如M.S.Chambers,E.J.Thomas,D.J.Williams,J.Chem.Soc.Chem.Commun.,(1987),1228)。
式(ⅩⅩⅫ)苄基硫基-羧酸卤化物在某些情况下是已知的和/或可以通过已知的方法制备(抗生素杂志(J.Antibiotics)(1983),26,1589)。
在方法(D)中需要用作起始物的式(Ⅵ)的卤代羰基烯酮是新的。其可以通过原则上已知的方法以简单的方式制备(参见,例如,Org.Prep.Proced.Int.7,(4),155-158,1975和DE 1945703)。当如果适当在催化剂例如二乙基甲酰胺,甲基-steryl甲酰胺或三苯基膦存在下,和,如果适当,在碱例如吡啶或三乙胺存在下,在-20℃和200℃之间的温度下,优选在0℃和150℃之间,式(ⅩⅩⅩⅢ)的取代的吡啶基丙二酸与酸的卤化物例如亚硫酰氯,氯化磷(Ⅴ),氯化磷(Ⅲ),草酰氯,光气或亚硫酰溴反应,得到式(Ⅵ)化合物其中W,V1,V2,V3,n和Z具有上述定义,和Hal代表氯或溴,其中W,V1,V2,V3,n和Z具有上述定义。
式(ⅩⅩⅩⅢ)的取代的吡啶基丙二酸是新的。但是其可以通过已知的方法以简单的方式制备(参见,例如,Organikum,VEB DeutscherVerlag der Wissenschaften,柏林1977,p.517及其后各页),例如通过水解式(ⅩⅩⅩⅣ)的取代的吡啶基丙二酸酯制备其中W,V1,V2,V3,n,Z和R8具有上述定义。
在本发明方法(E)中需要用作起始物的式(Ⅵ)的烯酮酸的氯化物的制备已经在本发明方法(D)中描述。在本发明方法(E)中需要用作起始物的式(Ⅶ)的硫代酰胺是一般在有机化学中已知的化合物其中A具有上述定义。
式(ⅩⅩⅩⅣ)的丙二酸酯是新的其中R8,W,V1,V2,V3,n和Z具有上述定义。其一般通过有机化学已知的方法制备(参见,例如,TetrahedronLett.27,2763(1986)和Organikum,VEB Deutscher Verlag derWissenschaften,柏林1977,p.587及其后各页)。
进行本发明方法(F),(G),(H),(I),(J),(K)和(L)还需要用作起始物的所有化合物式(Ⅷ)的酸的卤化物,式(Ⅸ)的酸酐,式(Ⅹ)的氯甲酸酯或氯甲酸硫代酯,式(Ⅺ)的氯一硫代甲酸酯或氯二硫代甲酸酯,式(Ⅻ)的烷基卤化物,式(ⅩⅢ)的磺酰氯,式(ⅩⅣ)的磷化合物和式(ⅩⅤ)和(ⅩⅥ)的金属氢氧化物、金属烷氧化物或胺,式(ⅩⅦ)的异氰酸酯和式(ⅩⅧ)的氨基甲酰氯一般是有机或无机化学已知的化合物。
另外,式(Ⅴ),(Ⅴa),(Ⅶ)至(ⅩⅨ),(ⅩⅫ),(ⅩⅩⅧ),(ⅩⅩⅩ),(ⅩⅩⅪ)和(ⅩⅩⅫ)化合物在附录引述的专利申请中公开和/或可以通过这里给出的方法制备。
方法(A)的特征在于,在稀释剂存在下和在碱存在下使其中A,B,R8,W,V1,V2,V3,n,Z和R8具有上述定义的式(Ⅱ)化合物进行分子内缩合反应。
可以在本发明方法(A)中使用的稀释剂是对反应物呈惰性的所有的有机溶剂。优选使用下面的溶剂:烃类,例如甲苯和二甲苯,还有醚类,例如丁醚,四氢呋喃,二噁烷,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮,和醇类,例如甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇和叔丁醇。
在进行本发明方法(A)时使用的碱(去质子试剂)是所有的常规质子受体。优选使用下面的碱:碱金属氧化物,碱金属氢氧化物,碱金属碳酸盐,碱土金属氧化物,碱土金属氢氧化物和碱土金属碳酸盐,例如,氢氧化钠,氢氧化钾,氧化镁,氧化钙,碳酸钠,碳酸钾和碳酸钙,所有这些碱也可以在相转移催化剂例如三乙基苄基氯化铵,四丁基溴化铵,Adogen 464(=甲基三烷基(C8-C10)氯化铵)或TDA1(=三-(甲氧基乙氧基乙基)-胺)存在下使用。此外,可以使用碱金属例如钠或钾。还可以使用的物质是碱金属氨化物,碱金属氢化物,碱土金属氨化物和碱土金属氢化物,例如氨基钠,氢化钠和氢化钙,此外还有碱金属烷氧化物,例如甲醇钠,乙醇钠和叔丁醇钾。
进行本发明方法(A)时,反应温度在一个大的范围内变化。一般情况下,在-70℃和150℃之间的温度下进行该反应,优选在-50℃和100℃之间。
本发明方法(A)一般在大气压下进行。
进行本发明方法(A)时,一般以等摩尔至大约二倍摩尔的量使用式(Ⅱ)反应物和去质子碱。但是,也可以以较大过量使用一种或另一种组分(至多3mol)。
方法(B)的特征在于,在稀释剂存在下和在碱存在下,使其中A,B,W,V1,V2,V3,n,Z和R8具有上述定义的式(Ⅲ)化合物进行分子内缩合反应。
可以在本发明方法(B)中使用的稀释剂是对反应物呈惰性的所有的有机溶剂。优选使用下面的溶剂:烃类,例如甲苯和二甲苯,还有醚类,例如丁醚,四氢呋喃,二噁烷,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮,和醇类,例如甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇和叔丁醇。
在进行本发明方法(B)时使用的碱(去质子试剂)是所有的常规质子受体。优选使用下面的碱:碱金属氧化物,碱金属氢氧化物,碱金属碳酸盐,碱土金属氧化物,碱土金属氢氧化物和碱土金属碳酸盐,例如,氢氧化钠,氢氧化钾,氧化镁,氧化钙,碳酸钠,碳酸钾和碳酸钙,所有这些碱也可以在相转移催化剂例如三乙基苄基氯化铵,四丁基溴化铵,Adogen 464(=甲基三烷基(C8-C10)氯化铵)或TDA 1(=三-(甲氧基乙氧基乙基)-胺)存在下使用。此外,可以使用碱金属例如钠或钾。还可以使用的物质是碱金属氨化物,碱金属氢化物,碱土金属氨化物和碱土金属氢化物,例如氨基钠,氢化钠和氢化钙,此外还有碱金属烷氧化物,例如甲醇钠,乙醇钠和叔丁醇钾。
进行本发明方法(B)时,反应温度在一个大的范围内变化。一般情况下,在-75℃和150℃之间的温度下进行该反应,优选在-50℃和100℃之间。
本发明方法(B)一般在大气压下进行。
进行本发明方法(B)时,一般以大约等摩尔量使用式(Ⅲ)反应物和去质子碱。但是,也可以以较大过量使用一种或另一种组分(至多3mol)。
方法(C)的特征在于,在酸存在下和如果适当,在稀释剂存在下,使其中A,B,T,W,V1,V2,V3,n,Z和R8具有上述定义的式(Ⅳ)化合物进行分子内环化反应。
可以在本发明方法(C)中使用的稀释剂是对反应物呈惰性的所有的有机溶剂。优选使用下面的溶剂:烃类,例如甲苯和二甲苯,还有卤代烃,例如二氯甲烷,氯仿,二氯乙烷,氯苯,二氯苯,还有极性溶剂例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮,此外也可以使用醇类,例如甲醇,乙醇,丙醇,异丙醇,丁醇,异丁醇和叔丁醇。
如果适当,也可以使用酸作为稀释剂。
可以在本发明方法(C)中使用的酸是所有的无机酸和有机酸,例如氢卤酸,硫酸,烷基-、芳基-和卤代烷基磺酸;特别是卤代烷基羧酸,例如使用三氟乙酸。
进行本发明方法(C)时,反应温度在一个大的范围内变化。一般情况下,在0℃和250℃之间的温度下进行该反应,优选在50℃和150℃之间。
本发明方法(C)一般在大气压下进行。
进行本发明方法(C)时,一般以例如等摩尔量使用式(Ⅳ)反应物和酸。但是,如果适当,也可以以催化量使用酸。
本发明方法(D)的特征在于,如果适当在稀释剂存在下和如果适当在酸受体存在下,其中A和B具有上述定义的式(Ⅴ)的羰基化合物或式(Ⅴa)的其甲硅烷基烯醇醚与与其中W,V1,V2,V3,n和Z具有上述定义的式(Ⅵ)烯酮酸的卤化物反应。
可以在本发明方法(D)中使用的稀释剂是对反应物呈惰性的所有的有机溶剂。优选使用下面的溶剂:烃类,例如邻二氯苯,四氢化萘,甲苯和二甲苯,还有醚类,例如丁醚,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮。
进行本发明方法(D)时使用的酸受体是所有常规的酸受体。
优选使用下面的物质:季胺,例如三乙胺,吡啶,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU),二氮杂双环壬烯(DBN),Hunig碱或N,N-二甲基-苯胺。
进行本发明方法(D)时,反应温度在一个大的范围内变化。有利的是,在0℃和250℃之间的温度下进行该反应,优选在50℃和220℃之间。
本发明方法(D)优选在大气压下进行。
进行本发明方法(D)时,一般以大约等摩尔量使用式(Ⅴ)和式(Ⅵ)反应物和如果适当,酸受体。但是,也可以以较大过量使用一种或另一种组分(至多5mol)。
本发明方法(E)的特征在于,如果适当在稀释剂存在下和如果适当在酸受体存在下,其中A具有上述定义的式(Ⅶ)硫代酰胺与其中W,V1,V2,V3,n和Z具有上述定义的式(Ⅵ)烯酮酸的卤化物反应。
可以在本发明变化方法(E)中使用的稀释剂是所有的惰性有机溶剂。优选使用下面的溶剂:烃类,例如邻二氯苯,四氢化萘,甲苯和二甲苯,还有醚类,例如丁醚,乙二醇二甲基醚和二甘醇二甲基醚,还有极性溶剂例如二甲亚砜,环丁砜,二甲基甲酰胺和N-甲基-吡咯烷酮。
进行本发明方法(E)时使用的酸受体是所有常规的酸受体。
优选使用下面的物质:季胺,例如三乙胺,吡啶,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU),二氮杂双环壬烯(DBN),Hunig碱或N,N-二甲基-苯胺。
进行本发明方法(E)时,反应温度在一个大的范围内变化。有利的是,在0℃和250℃之间的温度下进行该反应,优选在20℃和220℃之间。
本发明方法(E)优选在大气压下进行。
进行本发明方法(E)时,一般以大约等摩尔量使用式(Ⅶ)和式(Ⅵ)反应物和如果适当,酸受体。但是,也可以以较大过量使用一种或另一种组分(至多5mol)。
本发明方法(Fα)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(Ⅷ)羧酸卤化物反应。
可以在本发明变化方法(Fα)中使用的稀释剂是对酸卤化物呈惰性的所有的有机溶剂。优选使用下面的溶剂:烃类,例如汽油,苯,甲苯,二甲苯和四氢化萘,还有卤代烃,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,还有醚类,例如乙醚,四氢呋喃和二噁烷,还有羧酸酯,例如乙酸乙酯,还有强极性溶剂例如二甲亚砜,环丁砜和二甲基甲酰胺。如果酸卤化物对水解足够稳定,则反应也可以在水存在下进行。
进行本发明方法(Fα)反应的合适的酸结合剂是所有常规的酸受体。优选使用下面的物质:季胺,例如三乙胺,吡啶,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU),二氮杂双环壬烯(DBN),Hünig碱或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,还有碱金属碳酸盐和碱土金属碳酸盐,例如碳酸钠,碳酸钾和碳酸钙,还有碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
进行本发明方法(Fα)时,反应温度在一个大的范围内变化。一般情况下,在-20℃和150℃之间的温度下进行该反应,优选在0℃和100℃之间。
进行本发明方法(Fα)时,各种情况下一般以大约等摩尔量使用式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物和(Ⅷ)羧酸卤化物。但是,也可以以较大过量使用羧酸卤化物(至多5mol)。通过常规方法进行后处理。
本发明方法(Fβ)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(Ⅸ)羧酸酸酐反应。
可以在本发明变化方法(Fβ)中使用的稀释剂优选是当使用酸卤化物时也适合的那些稀释剂。除此以外,以过量使用的羧酸酐同时也可以作为稀释剂。
方法(Fβ)中被任选加入的酸结合剂是当使用酸卤化物时也适合的那些酸受体。
进行本发明方法(Fβ)时,反应温度在一个大的范围内变化。一般情况下,在-20℃和+150℃之间的温度下进行该反应,优选在0℃和100℃之间。
进行本发明方法(Fβ)时,各种情况下一般以大约等摩尔量使用式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物和(Ⅸ)羧酸酐。但是,也可以以较大过量使用羧酸酐(至多5 mol)。通过常规方法进行后处理。
一般情况下,接着进行一个步骤,其中稀释剂和过量的羧酸酐以及生成的羧酸通过蒸馏或通过用有机溶剂或者用水洗涤除去。
本发明方法(G)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(Ⅹ)氯甲酸酯或氯甲酸硫代酯反应。
适合于本发明方法(G)的酸结合剂是所有常规的酸受体。优选使用下面的物质:季胺,例如三乙胺,吡啶,DABCO,DBU,DBA,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,还有碱金属碳酸盐和碱土金属碳酸盐,例如碳酸钠,碳酸钾和碳酸钙,还有碱金属氢氧化物,例如氢氧化钠和氢氧化钾。
可以在本发明变化方法(G)的稀释剂是对氯甲酸酯或氯甲酸硫代酯呈惰性的所有溶剂。优选使用下面的溶剂:烃类,例如汽油,苯,甲苯,二甲苯和四氢化萘,还有卤代烃,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,还有醚类,例如乙醚,四氢呋喃和二噁烷,还有羧酸酯,例如乙酸乙酯,还有腈类,例如乙腈,还有强极性溶剂例如二甲亚砜,环丁砜和二甲基甲酰胺。
进行本发明方法(G)时,反应温度在一个大的范围内变化。一般情况下,在-20℃和100℃之间的温度下进行该反应,优选在0℃和50℃之间。
本发明方法(G)一般在大气压下进行。
进行本发明方法(G)时,各种情况下一般以大约等摩尔量使用式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物和相关的式(Ⅹ)氯甲酸酯或氯甲酸硫代酯。但是,也可以以较大过量使用一种或另一种组分(至多2 mol)。通过常规方法进行后处理。一般情况下,接着进行其中沉淀的盐被去除并且通过汽提掉溶剂来浓缩留下的反应混合物这一步骤。
本发明方法(H)的特征在于,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下,(Hα)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(Ⅺ)化合物反应,或者(Hβ)如果适当在稀释剂存在下和如果适当在碱存在下与二硫化碳并接着与式(Ⅻ)烷基卤化物反应。
在制备方法(Hα)中,在0-120℃,优选在20-60℃下,对于每摩尔式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物使大约1mol式(Ⅺ)氯一硫代甲酸酯或氯二硫代甲酸酯反应。
任选加入的合适的稀释剂是所有惰性有机溶剂,例如醚类,酰胺,砜,亚砜,还有卤代烷。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
在优选的实施方案中,如果通过加入强去质子试剂,例如氢化钠或叔丁醇钾,来合成(Ⅰ-1-a)至式(Ⅰ-5-a)化合物的烯醇盐,则可以省掉另外加入酸结合剂。
如果使用酸结合剂,则合适的物质是常规无机碱或有机碱,作为例子可以提到氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
该反应在大气压或高压下反应,优选在大气压下进行。通过常规方法进行后处理。
在制备方法(Hβ)中,各种情况下对于每摩尔式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物加入等摩尔或过量二硫化碳。该方法优选在0-50℃,特别是在20-30℃温度下进行。
通常情况下,有利的是,首先通过加入碱(例如叔丁醇钾或氢化钠)从式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物制备相应的盐。式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与二硫化碳反应,直到完全形成中间体,例如在室温下搅拌几小时后。
可以在方法(Hβ)中使用的碱是所有常规质子受体。优选使用下面的碱:碱金属氢化物,碱金属烷氧化物,碱金属碳酸盐,碱金属碳酸氢盐,碱土金属碳酸盐,碱土金属碳酸氢盐,或者氮碱。可以提到的例子是氢化钠,甲醇钠,氢氧化钠,氢氧化钙,碳酸钾,碳酸氢钾,三乙胺,二苄基胺,二异丙基胺,吡啶,喹啉,二氮杂双环辛烷(DABCO),二氮杂双环十一烯(DBU)和二氮杂双环壬烯(DBN)。
可以在该方法中使用的稀释剂是所有常规溶剂。
优选使用下面的物质:芳烃,例如苯或甲苯,醇类,例如甲醇,乙醇,异丙醇或乙二醇,腈类,例如乙腈,醚类,例如四氢呋喃或二噁烷,酰胺类,例如二甲基甲酰胺,或者其它极性溶剂,例如二甲亚砜或环丁砜。
进一步与式(Ⅻ)烷基卤化物的反应优选在0-70℃,特别是在20-50℃下进行。使用至少等摩尔量的烷基卤化物。
该反应在大气压或高压下进行,优选在大气压下进行。
同样,通过常规方法进行后处理。
本发明方法(Ⅰ)的特征在于,如果适当在稀释剂存在下和,如果适当在酸结合剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅢ)磺酰氯反应。
在制备方法(Ⅰ)中,在-20至150℃,优选在0-70℃下,对于每摩尔式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物使大约1mol式(ⅩⅢ)磺酰氯反应。
优选在稀释剂存在下进行方法(Ⅰ)。
合适的稀释剂是所有惰性极性有机溶剂,例如醚类,酰胺类,酮类,羧酸酯,腈类,砜,亚砜或卤代烃例如二氯甲烷。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
在优选的实施方案中,如果通过加入强去质子试剂(例如氢化钠或叔丁醇钾)来合成(Ⅰ-1-a)至式(Ⅰ-5-a)化合物的烯醇盐,则可以省掉另外加入酸结合剂。
如果使用酸结合剂,则合适的物质是常规无机碱或有机碱,作为例子可以提到氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
该反应在大气压或高压下进行,优选在大气压下进行。通过常规方法进行后处理。
本发明方法(J)的特征在于,如果适当在稀释剂存在下和如果适当在酸结合剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅣ)磷化合物反应。
在制备方法(J)中,在-40℃和150℃之间的温度下,优选在-10℃至110℃之间,1-2,优选1-1.3mol式(ⅩⅣ)磷化合物反应,得到式(Ⅰ-1-e)至式(Ⅰ-5-e)化合物。
优选在稀释剂存在下进行方法(J)。
合适的稀释剂是所有惰性极性有机溶剂,例如醚类,羧酸酯,卤代烃,酮类,酰胺类,腈类,砜,亚砜等。
优选使用的物质是乙腈,二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
任选加入的酸结合剂是常规无机碱或有机碱,例如氢氧化物,碳酸盐或胺类,作为例子可以提到氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
该反应在大气压或高压下进行,优选在大气压下进行。通过有机化学常规方法进行后处理。终产物优选通过结晶,色谱或者通过称之为“初期蒸馏”即真空去除挥发成分的方法来纯化。
本发明方法(K)的特征在于,如果适当在稀释剂存在下,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下与式(ⅩⅤ)金属氢氧化物或金属烷氧化物,或者式(ⅩⅥ)胺反应。
本发明方法(K)中使用的稀释剂优选醚类,例如四氢呋喃,二噁烷,乙醚,或者还有醇类,例如甲醇,乙醇和异丙醇,还有水。本发明方法(K)一般在大气压下进行。反应温度一般在-20℃和100℃之间,优选在0℃至50℃之间。
本发明方法(L)的特征在于,式(Ⅰ-1-a)至式(Ⅰ-5-a)化合物在各种情况下,(Lα)如果适当在稀释剂存在下和如果适当在催化剂存在下,与式(ⅩⅦ)化合物反应,或者(Lβ)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(ⅩⅧ)化合物反应。
在制备方法(Lα)中,在0-100℃,优选在20-50℃下,对于每摩尔式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物使大约1mol式(ⅩⅦ)异氰酸酯反应。
方法(Lα)优选在稀释剂存在下进行。
合适的稀释剂是所有惰性有机溶剂,例如芳烃,卤代烃,醚类,酰胺类,腈类,砜或亚砜。
如果适当,可加入催化剂以加快反应。可以使用的非常有益的催化剂是有机锡化合物,例如二月桂酸二丁基锡。
该反应优选在大气压下进行。
在制备方法(Lβ)中,在0-150℃,优选在20-70℃温度下,对于每摩尔式(Ⅰ-1-a)至式(Ⅰ-5-a)起始物使大约1mol式(ⅩⅧ)氨基甲酰氯反应。
任选加入的合适的稀释剂是所有惰性极性有机溶剂,例如醚类,羧酸酯,腈类,酮类,酰胺类,砜,亚砜或卤代烃。
优选使用二甲亚砜,四氢呋喃,二甲基甲酰胺或二氯甲烷。
在优选的实施方案中,如果通过加入强去质子试剂(例如氢化钠或叔丁醇钾)来合成(Ⅰ-1-a)至式(Ⅰ-5-a)化合物的烯醇盐,则可以省掉另外加入酸结合剂。
如果使用酸结合剂,则合适的物质是常规无机碱或有机碱,作为例子可以提到氢氧化钠,碳酸钠,碳酸钾,吡啶和三乙胺。
该反应在大气压或高压下进行,优选在大气压下进行。通过常规方法进行后处理。
这些活性化合物适于防治动物害虫,优选节肢动物和线虫,特别是农业,林业,储藏品保护和材料保护以及卫生领域所遇到的昆虫和蛛形纲虫。其活性抗一般敏感性和抗性物种,并且在害虫发育的所有阶段或部分阶段有效。上述害虫包括:等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber。多足纲目(Diplopoda),例如Blaniulus gutttulatus。唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.)。综合纲目(Symphyla),例如Scutigerella immaculata。缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina)。弹尾目(Collembola),例如Onychiurus armatus。直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria。革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia)。等翅目(Isoptera),例如白蚁属(Reticulitermes spp.)。虱目(Anoplura),例如Phylloxera vastatrix,瘿绵蚜属(Pemphigus),头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.)。食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalinea spp.。缨翅目(Thysanoptera),例如温室条蓟马(Hercinothripsfemoralis)和棉蓟马(Thrips tabaci)。异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatoma spp.)。同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisiatabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphisgossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Doralis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Macrosiphum avenae,瘤额蚜(Myzus spp.),忽布瘤额蚜(Phorodonhumuli),粟缢管蚜(Rhopasiphum padi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotus hederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletis blancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutella maculipennis),天幕毛虫(Malacosomaneustria),Euproctis chrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrix thurberiella),Phyllocnisticitrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Felti8 spp.),埃及金刚钻(Earias insulana),夜蛾属(Heliothisspp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestrabrassicae),Panolis flammea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilospp.),Pyrausta nubilalis,Ephestia kuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineola bisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophilapseudospretella),Cacoecia podana,Capua reticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysiaambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana)。鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,大豆象(Acanthoscelides obtectus),家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomaria spp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomus spp.),米象属(Sitophilus spp.),Otiorrhynchus sulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenus spp.),黑皮蠹(Attagenuespp.),粉蠹(Lyctus spp.),Meligethes aeneus,蛛甲属(Ptinusspp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbiumpsylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebriomolitor),扣甲属(Agriotes spp.),金针虫属(Conoderus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica。膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomoriumpharaonis),和胡蜂(Vespa spp.)。双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culexspp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydodermaspp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyia hyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacus oleae)和欧洲大蚊(Tipudosa)。蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis),和角叶蚤属(Ceratophyllus spp.)。蛛形纲(Arachnida),例如Sciopio maurus,黑寡妇球腹蛛(Latrodectus mactans)。蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptesspp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
本发明活性化合物的特征在于有有效的杀昆虫和杀螨活性。
本发明化合物对于防治植物病原害虫能被特别成功地应用,例如杀辣根猿叶甲幼虫(Phaedon cochleariae),或者杀黑尾叶蝉(Nephotettix cincticeps)幼虫或者杀小菜蛾毛虫(Plutella
本发明活性化合物还可以用作脱叶剂,干燥剂,杀稻草剂,特别是作为杀杂草剂。从广义上说,所谓杂草被理解是在其所不期望的地点生长的所有植物。本发明物质是作为总的除草剂还是选择性除草剂主要取决于使用的量。
需要用来防治杂草的本发明活性化合物的剂量比在0.001和10kg/ha之间,优选在0.005和5 kg/ha之间。
例如,与下面的植物相关,可以使用本发明活性化合物:双子叶杂草种类:芥属(Sinapis),独行菜属(Lepidium),猪殃殃属(Galium),繁缕属(Stellaria),母菊属(Matricaria),春黄菊属(Anthemis),辣子草(Galinsoga),藜属(Chenopodium),荨麻属(Urtica),千里光属(Senecio),苋属(Amaranthus),马齿苋属(Portulaca),苍耳属(Xanthium),旋花属(Convolvulus),甘薯属(Ipomoea),蓼属(Polygonum),田菁(Sesbania),豚草属(Ambrosia),蓟属(Cirsium),飞廉属(Carduus),苦苣菜属(Sonchus),茄属(Solanum),焊菜属(Rorippa),水松叶属(Rotala),母草属(Lindernia),野芒麻属(Lamium),婆婆纳属(Veronica),苘麻属(Abutilon),刺果(Emex),曼陀罗属(Datura),堇菜属(Viola),鼬瓣花属(Galeopsis),罂粟属(Papaver),矢车菊属(Centaurea),车轴草属(Trifolium),毛茛属(Ranunculus)和蒲公英属(Taraxacum)。双子叶作物种类:棉属(Gossypium),Glycine,Beta,胡萝卜属(Daucus),菜豆属(Phaseolus),Pisum,茄属(Solanum),亚麻属(Linum),甘薯属(Ipomoea),巢菜属(Vicia),烟草属(Nicotiana),番茄属(Lycopersicon),花生(Arachis),芥属(Brassica),莴苣属(Lactuca),Cucumis,和臭瓜(Cucurbita)。单子叶杂草种类:稗属(Echinochloa),狗尾草属(Setaria),黍属(Panicum),马唐属(Digitaria),梯牧属(Phleum),早熟禾属(Poa),羊茅属(Festuca),蟋蟀菜属(Eleusine),臂形草属(Brachiaria),黑麦草属(Lolium),雀麦属(Bromus),燕麦属(Avena),莎草属(Cyperus),蜀黍属(Sorghum),冰草属(Agropyron),Cycnodon,雨久花属(Monchoria),飘拂草属(Fimbristylis),慈姑(Sagittaria),荸荠属(Eleocharis),镳草(Scirpus),雀稗草(Paspalum),Ischaemum,尖瓣花属(Sphenoclea),龙爪茅属(Dactyloctenium),剪股颍属(Agrostis),看麦娘属(Alopecurus),和Apera。单子叶作物种类:稻属(Oryza),玉米属(Zea),小麦属(Triticum),大麦属(Hordeum),燕麦属(Avena),黑麦属(Secale),蜀黍属(Sorghum),黍属(Panicum),甘蔗(Saccharum),菠萝(Ananas),天门冬属(Asparagus)和葱属(Allium)。
但是,本发明活性化合物的用途不受这些种类的限制,而是以相同的方式扩展到其它植物。
根据浓度,本发明化合物适于例如在工业场所和铁道,有或没有树木的路或广场上全部控制杂草。这些化合物也同样被用来在多年生种植植物场所,草坪,运动场和牧场控制杂草,所述多年生种植植物场所是例如树林,装饰性种植的树,果园,葡萄园,柠檬园,坚果园,香蕉种植园,咖啡种植园,茶种植园,橡胶种植园,油棕种植园,可可种植园,软果种植植物和蛇麻草田,以及用来在年生农作物场所选择性控制杂草。
本发明活性化合物高度适用于在芽前和芽后选择性控制双子叶农作物中的单子叶杂草,例如其非常成功地用于控制棉花或甜菜中的禾本科杂草。
活性化合物可以配制成常规制剂,例如溶液、混悬剂、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料,和包裹在聚合物中的细微胶囊。
这些型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/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳族化合物如二甲苯,甲苯或烷基萘,氯代芳族化合物和氯代脂肪烃如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃如环己烷或石蜡例如矿物油馏份,矿物油和植物油,醇类如丁醇或乙二醇以及其醚和酯,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和二甲亚砜,以及水。
合适的固体载体是:
例如铵盐,磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱土或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎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:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;适合的分散剂有:例如,木素亚硫酸废液和甲基纤维素。
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。
也可以使用染料,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,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
本发明活性化合物可以以其商售制剂以及由这些制剂制备的使用形式,作为与其它活性化合物例如杀虫剂、引诱剂、杀菌剂、杀螨剂、杀线虫剂、杀真菌剂,生长调节剂或除草剂的混合物存在。杀虫剂包括例如磷酸酯,氨基甲酸酯,羧酸酯,氯代烃,苯基脲和由微生物产生的物质等。
特别有用的成分和混合物的例子如下:
杀真菌剂:
2-氨基丁烷;2-苯胺基-4-甲基-6-环丙基-嘧啶;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;2,6-二氯-N-(4-三氟甲基苄基)苯甲酰胺;(E)-2-甲氧基亚胺基-N-甲基-2-(2-苯氧基苯基)-乙酰胺;8-羟基喹啉硫酸盐;(E)-2-{2-[6-(2-氰基苯氧基)-嘧啶-4-基氧基]-苯基}-3-甲氧基丙烯酸甲酯;(E)-甲氧基亚胺基[α-(邻甲苯基氧基)-邻-甲苯基]乙酸乙酯;2-苯基苯酚(OPP),aldimorph,氨丙磷酸,敌菌灵,戊环唑,
苯霜灵,邻碘酰苯胺,苯菌灵,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,敌菌丹,克菌丹,多菌灵,萎锈灵,灭螨猛,地茂散,氯化苦,百菌消,乙菌利,代森锰,霜尿氰,环唑醇,酯菌胺,
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,二硝巴豆酸酯,二苯胺,吡菌硫,灭菌磷,二噻农,多果定,氨噁唑酮,克瘟散,epoxyconazole,乙嘧酚,土菌灵
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,fludioxonil,氟氯菌核利,fluquinconazole,氟硅唑,磺菌胺,氟酰胺,粉唑醇,灭菌丹,乙磷铝,四氯苯酞,麦穗宁,呋霜灵,拌种胺,
谷种定,
六氯苯,己唑醇,噁霉灵,
抑霉唑,酰胺唑,双瓣醋酸盐,异稻瘟净(IBP),异菌脲,稻瘟灵,
春雷霉素,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,嘧菌胺,灭锈胺,甲霜灵,metconazole,磺菌威,呋菌胺,代森联,噻菌胺,腈菌唑,
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,氧化萎锈灵,
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,环丙唑,丙森锌,吡嘧磷,啶斑肟,pyrimethanil,咯喹酮,
五氯硝基苯(PCNB),
硫和硫制剂,
戊唑醇,叶枯酞,四氯硝基苯,氟嘧唑,噻菌灵,噻菌腈,甲基硫菌灵,福美双,甲基立枯磷,甲基氟磺胺,三唑酮,三唑醇,唑菌嗪,杨菌胺,三环唑,十三吗啉,氟菌唑,嗪氨灵,triticonazole,
稻纹散,乙烯菌核利,
代森锌,福美锌。
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,AC303630,乙酰甲胺磷,氟酯菊酯,棉铃威,涕灭威,甲体氯氰菊酯,双虫脒,avermectin,AZ60541,azadirachtin,azinphos-A,保棉磷,三唑锡,
苏云金杆菌,噁虫威,丙硫克百威,杀虫磺,氟氯氰菊酯,氟氯菊酯,BPMC,brofenprox,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,丁硫克百威,杀螟丹,CGA1 57419,CGA184699,chloethocarb,chlorethoxyfos,毒虫畏,定虫隆,氯甲硫磷,毒死蜱,甲基毒死蜱,顺式-苄呋菊酯,clocythrin,四螨嗪,杀螟腈,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,酚线磷,敌敌畏,dicliphos,百治磷,乙硫磷,除虫脲,乐果,甲基毒虫畏,敌恶磷,乙拌磷,
克瘟散,emamectin,高氰戊菊酯,乙硫苯威,乙硫磷,醚菊酯,灭线磷,乙嘧硫磷,
虫胺磷,喹螨醚,苯丁锡,杀螟硫磷,仲丁威,苯硫威,双氧威,氯氰菊酯,fenpyrad,唑螨酯,倍硫磷,氰戊菊酯,fipronil,吡氟禾草灵,氟螨脲,氟氰戊菊酯,氟虫脲,flufenprox,氟胺氰菊酯,地虫硫磷,安果,噻唑磷,fubfenprox,呋线威,
HCH,庚烯磷,氟铃脲,噻螨酮,
吡虫啉,异稻瘟净,氯唑磷,异丙胺磷,叶蝉散,噁唑磷,ivermectin,
氯氟氰菊酯,lufenuron,
马拉硫磷,灭蚜蜱,速灭磷,mesulfenphos,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,moxidectin,
二溴磷,NC184,NI25,nitenpyram,
氧乐果,杀线威,亚砜吸磷,异砜磷,
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,甲基嘧啶磷,嘧啶磷-A,丙溴磷,猛杀威,丙虫磷,残杀威,丙硫磷,发果,pymetrozin,吡唑硫磷,pyradaphenthion,pyresmethrin,除虫菊酯,哒螨酮,pyrimidifen,蚊蝇醚,
喹硫磷,
RH5292,
蔬果磷,sebufos,silafluofen,治螟硫磷,甲丙硫磷,
tebufenozid,tebufenpyrad,tebupirimiphos,伏草隆,七氟菊酯,双硫磷,特灭威,特丁磷,杀虫畏,thiafenox,硫双威,久效磷,二甲硫吸磷,虫线磷,thuringiensin,四溴菊酯,苯噻螨,三唑磷,triazuron,敌百虫,杀虫隆,混灭威,
芽灭多,XMC,灭杀威,YI5301/5302,zetamethrin。
除草剂:
例如N-酰苯胺类,例如吡氟草胺和敌稗;芳基羧酸类,例如二氯吡啶甲酸,麦草畏和毒莠定;芳基氧基链烷酸类,例如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草烟,2甲4氯,2甲4氯丙酸和绿草定;芳基氧基-苯氧基-链烷酸酯类,例如禾草灵,噁唑禾草灵,吡氟禾草灵,吡氟氯禾灵和喹禾灵;吖嗪酮类,例如杀草敏和哒草伏;氨基甲酸酯类,例如氯苯胺灵,甜菜安,甜菜宁和苯胺灵;氯代N-乙酰苯胺类,例如甲草胺,乙草安,丁草安,吡草安,异丙甲草胺,丙草安和毒草安;二硝基苯胺类,例如安磺灵,二甲戊乐灵和氟乐灵;二苯基醚类,例如三氟羧草醚,甲羧除草醚,乙羧氟草醚,氟磺胺草醚,halosafen,乳氟禾草灵和乙氧氟草醚;脲类,例如氯麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆;羟胺类,例如禾草灭,烯草酮,噻草隆,稀禾定和肟草酮;咪唑啉酮类,例如咪草烟,咪草酯,灭草烟和灭草喹;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron,苄嘧黄隆,氯嘧黄隆,氯黄隆,醚黄隆,甲黄隆,烟嘧黄隆,氟嘧黄隆,吡嘧黄隆,噻黄隆,醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,例如克草猛,灭草特,燕麦畏,茵达灭,禾草畏,草达灭,苄草丹,杀草丹和野燕畏;三嗪类,例如莠去津,氰草津,西玛津,西草净,特丁净和terbutylazine;三嗪酮类,例如环嗪酮,苯嗪草酮和嗪草酮;其它类,例如氨基三唑,呋草黄,灭草松,环庚草醚,异噁草酮,二氯吡啶酸,双苯唑快,氟硫草定,乙呋草黄,氟咯草酮,草铵膦,草甘膦,isoxaben,哒草特,二氯喹啉酸,喹草酸,草硫磷和灭草环。
本发明活性化合物还可以以其商售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。增效剂是提高活性化合物作用而其自身没有活性的化合物。
由商售制剂制备的使用形式的活性化合物含量可以在宽范围内变化。使用形式中的活性化合物的浓度是0.0000001-95%重量活性化合物,优选0.0001-1%重量。
以适于这些使用形式的常规方式应用这些化合物。
当用来防治卫生领域害虫和储存产品害虫时,这些活性化合物的特征在于对木材和粘土的极好的残留作用,以及对用石灰处理过的物质上的碱的好的稳定性。
本发明活性化合物不仅对防治植物,卫生领域和储存产品害虫有活性,而且还用于兽药领域,杀寄生虫动物(定居寄生虫),例如硬蜱,软蜱,马痒螨,恙螨,蝇(叮和吮),寄生蝇幼虫,虱,头虱,鸟虱和蚤。这样的寄生虫包括:
虱目(Anolpurida),例如,血虱属(Haematopinus spp.),长颚虱(Linognathus spp.),虱属(Pediculus spp.),阴虱属(Phtirusspp.),管虱属(Solenopotes spp.)。
食毛目咬虱(Mallophagida)和Amblycerina及Ischnocerina亚目.例如毛羽虱属(Trimenopon spp.),Menopon spp.,巨羽虱属(Trinoton spp.),牛羽虱属(Bovicola spp.),Werneckiella spp.,Lepikentron spp.,Damalina spp.,Trichodectes spp.,Felcolaspp.。
双翅目(Diptera)和长角亚目(Nematocerina)和Brachycerina亚目,例如伊蚊(Aedes spp.),斑按蚊属(Anopheles spp.),库蚊(Culex spp.),蚋属(Simulium spp.),全毛真蚋(Eusimulium spp.),白蛉(Phlebotomus spp.),罗蛉属(Lutzomyia spp.),库蠓(Culicoides spp.),斑虻(Chrysops spp.),瘤虻(Hybomitra spp),Atylotus spp.,虻属(Tabanus spp.),麻虻属(Haematopotaspp.),Philipomyia spp.,Braula spp.,Musca spp.,齿股蝇属(Hydrotuea spp.),螫蝇(Stomoxys spp.),Haematobia spp.,Morellia spp.,厕蝇(Fannia spp.),Glossina spp.,Calliphoraspp.,Lucilia spp.,Chrysomyia spp.,Wohlfahrtia spp.,别麻蝇(Sarcophaga spp.),Oestrus spp.,皮蝇(Hypoderma spp.),Gasterophilus spp.,虱蝇(Hippobosca spp.),Lipoptena spp.,和Melophagus spp.。
蚤目(Siphonapterida),例如,蚤属(Pulex spp.),Ctenocephalides spp.,鼠蚤(Xenopsylla spp.),和角叶蚤(Ceratophyllus spp.)。
异翅亚目(Heteropterida),例如,臭虫属(Cimex spp.),吸血猎蝽属(Triatoma spp.),Rhodnius spp.,和全圆蝽属(Panstrongylusspp.)。
非蠊目(Blattarida),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),德国小蠊(Blattela germanica),非蠊属(Supella spp.)。
螨亚类(Acarida),和后胸气门目(Metastigmata)和中胸气门目(Mesostigmata),例如,隐喙蜱属(Argas spp.),喙蜱属(Ornithodorus spp.),耳残喙蜱(Otabius spp.),硬蜱(Ixodesspp.),花蜱属(Amblyomma spp.),牛蜱属(Boophilus spp.),矩头蜱(Dermacentor spp.),Haemophysalis spp.,璃眼蜱(Hyalommaspp.),头蜱属(Rhipicephalus spp.),鸡皮刺螨(Dermanyssusspp.),瑞立绦虫(Raillietia spp.),Pneumonyssus spp.,Sternostoma spp.,和Varroa spp.。
Actinedida(恙螨亚目,Prostigmata)和Acaridida(Astigmata),例如Acarapis spp.,姬螯螨属(Cheyletiella spp.),Ornithocheyletia spp.,Myobia spp.,疥螨(Psorergates spp.),蠕形螨(Demodex spp.),恙螨(Trombicula spp.),Listrophorusspp.,粗脚粉螨(Acarus spp.),酪螨(Tyrophagus spp.),嗜木螨(Caloglyphus spp.),Hypodectes spp.,翼衣螨属(Pterolichusspp.),恙螨(Psoroptes spp.),恙螨(Chorioptes spp.),Octodectes spp.,疥螨(Sarcoptes spp.),Notoedres spp.,足螨(Knemidocoptes spp.,),Cytodites spp.,和Laminosioptesspp.。
例如它们具有好的杀丝光绿蝇(Lucilla cuprina)和Boophilusmicroplus的出色的活性。
本发明活性化合物也适于杀死侵染农业生产家畜的节肢动物门,所述家畜是例如牛,绵羊,山羊,马,猪,驴,骆驼,水牛,兔子,鸡,火鸡,鸭,鹅,蜜蜂,其它宠物,例如狗,猫,笼养的鸟和鱼缸养殖鱼,和称之为实验室动物的动物,例如仓鼠,豚鼠,大鼠和小鼠。通过杀死这些节肢动物门,可以避免家畜死亡并且避免产品量的减少(产品例如肉,奶,羊毛,皮革,蛋,蜂蜜等),因此通过使用本发明活性化合物可以实现更经济更简单的动物的喂养。
在兽药领域,本发明活性化合物以已知方式经肠给药,例如以片剂,胶囊,顿服水剂,顿服药,颗粒剂,糊剂,巨丸剂,通过进食方法和栓剂的形式;通过肠胃外给药,例如通过注射(肌内,皮下,静脉内,腹膜内等),埋入,通过鼻给药,通过以例如浸渍或浸浴,喷洒,倾施和点施,洗用和撒粉的形式皮肤使用,也可以借助于含有活性化合物的用模子做的物品,例如颈圈,耳饰,尾饰,腿带,笼头,标记物等而使用。
当对牲畜,家禽,宠物等使用时,本发明式(Ⅰ)活性化合物可以作为以1-80%重量比的量含有活性化合物的制剂(例如粉末剂,乳剂,可流动性组合物)而被使用,直接使用或者稀释100-l0000倍后使用,或者可以用作化学浴。
另外,还发现本发明式(Ⅰ)化合物还具有杀破坏工业材料的昆虫的有效能的杀虫活性。
作为例子优选可以提到下面的昆虫,但是不受此限制:
甲虫,例如
家天牛(Hylotrupes bajulus),Chlorophorus pilosis,家具窃蠹(Anobium punctatum),Xestobium rufovillosum,Ptilinuspecticornis,Dendrobium pertinex,Ernobius mollis,Priobiumcarpini,欧洲竹粉蠹(Lyctus brunneus),Lyctus africanus,平颈粉蠹(Lyctus planicollis),Lyctus linearis,Lyctuspubescens,Trogoxylon aequale,Minthes rugicollis,小蠹虫种(Xyleborus spec.),Tryptodendron spec.,Apate monachus,Bostrychus capucins,Heterobostrychus branneus,Simoxylonspec.和竹长蠹(Dinoderus minutus)。
膜翅目(Hymenopterans),例如
钢青小树蜂(Sirex juvencus),枞大树蜂(Urocerus gigas),Urocerus gigas taignus和Urocerus augur。
白蚁,例如
Kalotermes flavicollis,Cryptotermes brevis,Heterotermes indicola,Reticulitermes flavipes,Reticulitermes santonensis,Reticulitermes lucifugus,澳洲白蚁(Mastotermes darwiniensis),Zootermopsis nevadensis和台湾家白蚁(Coptotermes formosanus)。
Bristle-tail,例如西洋衣鱼(Lepisma saccharina)。
本发明中所涉及的工业材料理解为非生命材料,例如,优选合成材料,粘合剂,胶料,纸和纸板,皮革,木材和木材加工产品以及涂料。
要保护使不受昆虫侵染的材料特别优选是木材和木材加工产品。
可以用本发明试剂或含有这样一种成分的混合物保护的木材和木材加工产品理解为是,例如建筑木材加工品,木梁,铁轨枕木,建桥木料,码头,木制运载工具,箱子,制模板,容器,电线杆,木桶,木窗,木门,胶合板,颗粒板,接合物,或者在房屋建筑或细木工行业很普通使用的木产品。
本发明活性化合物可以以其本身、乳油形式或者一般的常规制剂使用,例如粉末剂,颗粒剂,溶液,混悬剂,乳剂或糊剂。
上述制剂可以以本身已知的方法制备,例如通过混合活性化合物和至少一种溶剂或稀释剂,乳化剂,悬浮剂和/或粘合剂或固定剂,水驱避剂,如果合适,干燥剂和UV稳定剂和,如果合适,着色剂和颜料和其它加工助剂。
用于保护木料和木制品的杀虫剂组合物或浓缩物以0.0001-95%重量浓度含有本发明活性化合物,特别是0.001-60%重量。
使用的试剂或浓缩物的量取决于害虫的物种和发生情况,并取决于基质。施用的最佳比例每种情况下可以通过试验系列来决定。但是,一般情况下,使用以要保护的材料为基础的0.0001-20%重量,优选0.001-10%重量的活性化合物足够了。
使用的溶剂和/或稀释剂是有机化学溶剂或溶剂混合物和/或油或象油一样的有机化学溶剂或低挥发性溶剂混合物和/或极性有机化学溶剂或溶剂混合物和/或水和,如果合适,乳化剂和/或湿润剂。
优选使用的有机化学溶剂是具有大于35的挥发数和高于30℃,优选高于45℃的闪点的油状或类油溶剂。作为具有低挥发性并且在水中不溶解的这类油和油型溶剂而使用的物质是合适的矿物油或其芳香烃级分,或者含有矿物油的溶剂混合物,优选石油溶剂,石油和/或烷基苯。
有利地是使用沸点范围是170-220℃的矿物油,沸点范围是170-220℃的石油溶剂,沸点范围是250-350℃的锭子油,沸点范围是160-280℃的石油或芳香烃,松节油等。
在一个优选的实施方案中,使用的物质是沸点范围是180-210℃的液体脂肪烃或者沸点范围是180-220℃的芳香烃和脂肪烃的高沸点混合物和/或锭子油和/或一氯代萘,优选α-一氯代萘。
具有大于35的挥发数和高于30℃,优选高于45℃闪点的低挥发性有机油或油型溶剂可以部分替换成高挥发性或中等挥发性的有机化学溶剂,前提是该溶剂混合物也具有大于35的挥发数和高于30℃,优选高于45℃的闪点,并且杀虫剂/杀真菌剂混合物在该溶剂混合物中是可溶解的或可乳化的。
在优选的实施方案中,部分有机化学溶剂或溶剂混合物替换成脂肪族极性有机化学溶剂或溶剂混合物。优选使用的物质是具有羟基和/或酯基和/或醚基的脂肪族有机化学溶剂,例如乙二醇醚,酯等。
本发明范围内使用的有机化学粘合剂是本身已知的合成树脂和/或粘合干燥油,并且可以用水稀释和/或在使用的有机化学溶剂中是可溶解的,可分散的或可乳化的,特别是粘合剂由下面的物质组成或者含有下面的物质:丙烯酸树脂,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,苯酚树脂,烃类树脂,例如茚/苯并呋喃树脂,硅氧烷树脂,干燥植物油和/或干燥油和/或以天然和/或合成树脂为基础的物理干燥粘合剂。
作为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。最多10%重量的沥青或沥青状物质也可以作为粘合剂使用。另外,可以使用本身已知的着色剂,颜料,水驱避剂,气味掩蔽物质和抑制剂或防腐蚀剂等。
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的醇酸树脂,和/或干燥植物油作为有机化学粘合剂。根据本发明,优选使用的物质是油含量大于45%重量,优选50-68%重量的醇酸树脂。
上面提到的粘合剂的所有或部分可以替换成固定剂(混合物)或增塑剂(混合物)。这些添加剂是为了防止活性化合物的挥发和结晶或沉淀。优选替换0.01-30%的粘合剂(以使用的100%粘合剂为基础)。
增塑剂来自邻苯二甲酸酯类,例如邻苯二甲酸二丁酯,邻苯二甲酸二辛酯或邻苯二甲酸苄酯丁酯,磷酸酯,例如磷酸三丁酯,己二酸酯,例如己二酸二-(2-乙基己基)酯,硬脂酸酯,例如硬脂酸丁酯或硬脂酸戊酯,油酸酯,例如油酸丁酯,甘油醚或较高分子量的乙二醇醚,甘油酯和对甲苯磺酸酯。
固定剂的化学基础是聚乙烯基烷基醚,例如,聚乙烯基甲基醚,或酮类,例如二苯酮或二苯乙酮(ethylenebenzophenone)。
另一种合适的溶剂或稀释剂特别是水,如果合适,以与一种或几种上述有机化学溶剂或稀释剂,乳化剂和分散剂的混合物存在。
特别有效的木材保护作用是通过大量的工业化浸入方法实现的,例如真空,双倍真空或加压方法。
如果合适,即用型组合物可以另外含有其它的杀虫剂和,如果合适,另外一种或几种杀真菌剂。
可以混合的附加成分优选是WO94/29268中提到的杀虫剂和杀真菌剂。该文献中提到的化合物明确地是本申请的一部分。
可以混合的非常特别优选的成分是杀虫剂,例如毒死稗,辛硫磷,silafluofin,甲体氯氰菊酯,氟氯氰菊酯,氯氰菊酯,溴氰菊酯,氯菊酯,吡虫啉,NI-25,氟虫脲,氟铃脲和杀虫隆,和杀真菌剂,例如epoxyconazole,己唑醇,戊环唑,环丙唑,戊唑醇,环唑醇,metconazole,抑霉唑,苯氟磺胺,甲苯氟磺胺,氨基甲酸3-碘代-2-丙炔基丁酯,N-辛基-异噻唑啉-3-酮和4,5-二氯-N-辛基异噻唑啉-3-酮。
在0-10℃下,向30ml DMF中的8.82g(0.075mol)叔丁醇钾中滴加22ml DMF中的11.3 g实施例(Ⅱ-B-1)化合物,并将混合物在室温下搅拌。利用薄层色谱(TLC)来监测反应进程。当反应终止时加入250ml冰水,用0-10℃的浓盐酸酸化混合物,直到pH2,吸滤,滤液用水洗涤,干燥,并与甲基-叔丁基醚(MTB醚)/正己烷共沸来纯化。得到7.90g(理论量的77%)产物,m.p.>220℃。
类似于实施例-B-1-a-1,或者根据对于制备式(Ⅰ-1-a)化合物给出的一般信息,获得下面的式(Ⅰ-1-a)化合物:
表40
实施例编号 | V1 | V2 | V3 | W | Zn | A | B | 异构体 | M.p.℃ |
Ⅰ-B-1-a-2 | C-Cl | N | C-Cl | H | H | CH3 | CH3 | - | >220 |
Ⅰ-B-1-a-3 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | β | >220 | |
Ⅰ-B-1-a-4 | C-H | N | C-Cl | Cl | H | -(CH2)2-CHCH3-(CH2)2- | β | >220 | |
Ⅰ-B-1-a-5 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2 | β | >220 |
实施例(Ⅰ-B-1-b-1)
在回流温度下,向50ml无水乙酸乙酯中的2.34g实施例(Ⅰ-B-1-a-1)化合物和1.7ml(12mmol)三乙胺中滴加5 ml无水乙酸乙酯中的1.3ml(0.012mol)异丁酰氯,混合物在回流下搅拌,利用TLC来监测反应进程。反应终止后,浓缩反应混合物,溶解于二氯甲烷,用50ml 0.5N氢氧化钠洗涤两次,干燥并浓缩,残余物用MTB醚/正己烷重结晶。得到1.5g(理论量的51%)产物,m.p.204℃。
类似于实施例Ⅰ-B-1-b-1,或者根据对于该制备给出的一般信息,获得下面的式(Ⅰ-1-b)化合物:
表41
实施例编号 | V1 | V2 | V3 | W | Zn | A | B | R1 | 异构体 | M.p.℃ |
Ⅰ-B-1-b-2 | C-Cl | N | C-Cl | H | H | CH3 | CH3 | i-C3H7 | - | 149 |
Ⅰ-B-1-b-3 | C-Cl | N | C-Cl | H | H | CH3 | CH3 | C2H5-O-CH2 | - | 118 |
Ⅰ-B-1-b-4 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | i-C3H7 | β | 204 | |
Ⅰ-B-1-b-5 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | C2H5-O-CH2 | β | 190 | |
Ⅰ-B-1-b-6 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | 4-Cl-苯基 | β | 232 | |
Ⅰ-B-1-b-7 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | 2-噻吩基 | β | >220 |
实施例(Ⅰ-B-1-c-1)
在0-10℃下,向50ml无水二氯甲烷中的2.34g实施例(Ⅰ-B-1-a-1)化合物和1.2ml(0.008mol)三乙胺中滴加5ml无水二氯甲烷中的0.8ml(0.008mol)氯甲酸乙酯,混合物在回流下搅拌,利用TLC来监测反应进程。反应终止后,用50ml 0.5N氢氧化钠洗涤混合物两次,干燥并浓缩,残余物用MTB醚/正己烷重结晶。为了进一步纯化产物,再与乙酸乙酯共沸。得到1.6g(理论量的54%)产物,m.p.208℃。
类似于实施例Ⅰ-B-1-c-1,或者根据对于该制备给出的一般信息,获得下面的式(Ⅰ-1-c)化合物:
表42
实施例编号 | V1 | V2 | V3 | W | Zn | A | B | L | M | R2 | M.p.℃ | 异构体 |
Ⅰ-B-1-c-2 | C-Cl | N | C-Cl | H | H | CH2 | CH3 | O | O | C2H5 | 104 | - |
Ⅰ-B-1-c-3 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | O | O | C2H5 | >220 | β |
在90ml无水四氢呋喃(THF)中将9.5g顺-4-甲基-1-氨基-环己烷甲酸甲酯盐酸盐和12.8ml三乙胺搅拌5分钟。加入实施例(ⅩⅩⅢ-B-1)的7.8g 3-(2-氯)-吡啶基乙酸后再搅拌15分钟,加入17.8g(0.127mol)三乙胺,并且立即加入4.3ml磷酰氯,保持溶液中度沸腾。然后混合物回流30分钟。将混合物倒入400ml冰水中,并用二氯甲烷萃取,干燥并浓缩二氯甲烷相。残余物通过硅胶柱色谱纯化(洗脱剂是二氯甲烷/乙酸乙酯3:1)。得到11.3g(理论量的76%)产物,m.p.124℃。
类似于实施例Ⅱ-B-1,或者根据对于该制备给出的一般信息,获得下面的式(Ⅱ)化合物:
表43
实施例编号 | V1 | V2 | V3 | W | Zn | A | B | R8 | M.p.℃ | 异构体 |
Ⅱ-B-2 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | CH3 | 146 | β | |
Ⅱ-B-3 | C-Cl | N | C-Cl | H | H | CH3 | CH | CH3 | 138 | - |
Ⅱ-B-4 | C-Cl | N | C-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 122 | β | |
Ⅱ-B-5 | CH | N | C-Cl | Cl | H | -(CH2)2-CHCH3(CH2)2- | CH3 | 136 | β | |
Ⅱ-B-6 | CH | N | C-Cl | Cl | H | CH3 | CH3 | CH3 | 119 | - |
Ⅱ-B-7 | CH | N | C-Cl | Cl | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 137 | β |
室温下经5分钟向120ml无水乙腈中的50g(0.39mol)3-氨基-2-氯代吡啶中加入600g(6.05mol)1,1-二氯乙烯,并且继续搅拌5分钟。接着冷却下快速加入62.9g(0.47mol)无水CuCl2,然后室温下经5分钟滴加240ml乙腈中的70.8g亚硝酸异戊酯,接着在室温下搅拌混合物,直到停止挥发气体。然后将混合物倒入1600ml冰冷的20%强度的盐酸中,并用甲基叔丁基醚(MTB)反复萃取,有机相用20%强度的盐酸洗涤,干燥并浓缩。得到165g。粗产物不用进一步纯化即可用于合成实施例(ⅩⅩⅣ-B-1)化合物。
冷却下向150ml无水甲醇中165g实施例(ⅩⅩⅤ-B-1)的粗产物中滴加327ml 30%强度的碳酸氢钠水溶液。混合物在回流下搅拌5小时,接着在室温下滴加48ml浓硫酸,并在回流下继续搅拌1小时。
室温下向133ml无水THF中的13.1g(0.077mol)实施例(ⅩⅩⅣ-B-1)化合物(纯度90%)中滴加4g(0.095mol)氢氧化锂(纯度98%)在133ml水中的溶液,混合物在该温度下搅拌一天。通过HLC监测反应进程,而且,如果适当,加入更多的氢氧化锂。然后浓缩混合物,加入50ml水,并用MTB-醚萃取混合物。水相用3N盐酸酸化并用MTB-醚再萃取。使水相pH4-5。吸滤产物并干燥。得到7.6g(理论量的51%),m.p.:197℃。
1060g丙烯腈(1)和1120gDABCO在70℃下搅拌60小时。使混合物冷却,加入4L甲苯和5L水,有机相用1N盐酸洗涤,干燥并浓缩。残余物在O.5毫巴/150℃经膜蒸发器蒸馏。产率:380g,b.p.70-72℃/0.20毫巴。化合物(3)
70℃下,将1113g氯气通入500g化合物(2),250g四氯化碳和5.8g过氧化苯甲酰的混合物中。每小时再加入5.8g过氧化苯甲酰。接着浓缩混合物。粗产物不用进一步纯化即可用于化合物(4)的制备。产率:862g(理论量的Δ79%)。实施例(4)
将309.1g化合物(3),950ml乙酸和221.3g 78%强度硫酸回流2.5小时。冷却后,将混合物倒入大约1800ml冰水中,搅拌1.5小时并吸滤。粗产物各种情况下用3.5L水搅拌两次以上。吸滤,洗涤,直到中性,并在50℃干燥。产率:64.3%,m.p.131-132℃。实施例(5)
160℃5巴氮气压下220g化合物(4)与1.2L POCl3加热3小时。蒸馏过量的POCl3,残余物搅拌下倒入冰中,吸滤,用水充分洗涤,并在40℃干燥。产率:68%,NMR(200 MHz,CDCl3):δ=4.65(s,2H,CH2-Cl),7.32(d,1H,pyrid 3-H),7.83(d,1H,pyrid.6-H)化合物(6)
60-80℃下,将100ml甲苯中的106g(0.5mol)化合物(5)(纯度94.5%)的溶液缓慢滴加到50ml水中的31g(0.64mol)NaCN和1gAliquat336的混合物中,混合物在80℃搅拌8小时。加入31g NaCN和1g Aliquat 336后,混合物在80℃再搅拌8小时。冷却后,在各种情况下,加入100ml水和甲苯,有机相每种情况下用300ml饱和的氯化钠水溶液洗涤两次,干燥并浓缩,残余物在高真空下蒸馏。产率:29%,m.p.80-82℃。实施例(ⅩⅩⅢ-B-2)
80-90℃下,向119.3ml浓硫酸和141.3ml水的混合物中加入24.2g(0.127mol)化合物(6),混合物在回流下搅拌2小时。冷却后,将混合物倒入500ml冰水中,吸滤,用冰水洗涤,直到中性,干燥。产率:74%,m.p.134-135℃。实施例(ⅩⅩⅢ-B-3)
根据下面的反应式制备该化合物:化合物(8)
249g丙酮二羧酸二乙酯(7),233.4g乙酸酐和164.4g原甲酸三乙酯在140℃下搅拌1小时。蒸馏出在最高120℃挥发的所有的成分,并且将混合物冷却至室温。接着加入450ml 25%强度NH3,并且吸滤出沉淀。将其悬浮于水中。用浓盐酸将悬浮液调至pH1,并吸滤,产物干燥过夜。粗产物在1升甲苯中煮沸,吸滤并干燥。产率:107.5g(理论量的51%),m.p.214℃。化合物(9)
11.0g化合物(8)在67ml POCl3中回流7小时。蒸馏出大部分过量的POCl3,并将残余物倒入冰水中。通过加入碳酸钠将混合物调至pH5,并且用二氯甲烷萃取,二氯甲烷相被干燥,浓缩和蒸馏。产率:8.3g(理论量的63%),b.p.83℃/0.3毫巴。化合物(10)
在5-10℃下,一次加入一点,经大约1小时,将8,6g氢化锂铝加入到66.02g化合物(9)的120ml无水四氢呋喃(THF)溶液中,混合物在该温度下再搅拌2小时。然后,在5-8℃下滴加250ml 3N盐酸,并将反应混合物蒸发至干。混合物用二氯甲烷萃取,干燥,浓缩,并通过柱色谱纯化,用乙酸乙酯/环己烷1/2为洗脱剂。产率:32.9g(理论量的61%),m.p.83℃。化合物(11)
0.94g化合物(10)与7ml POCl3一起回流下沸腾19小时。蒸馏出过量的POCl3后,将残余物倒入冰水中。吸滤出粗产物,用水洗涤并空气风干。产率:0.25g(理论量的26%),m.p.53℃。化合物(12)
室温下,向50ml二氯甲烷中的10.27g化合物(11)和0.9g四丁基硫酸铵中滴加9.8g KCN的38ml水溶液,混合物在室温下搅拌过夜。然后浓缩有机相,残余物在硅胶上进行色谱,用乙酸乙酯/环己烷1/2洗脱。产率:6.0g(理论量的63%),m.p.56℃。(ⅩⅩⅢ-B-3)
在4.8ml浓硫酸和5.7ml水中使1g化合物(12)回流2小时。冷却后,将混合物倒入20ml冰水中,并吸滤,洗涤产物至中性并干燥。产率:0.85g(理论量的81%),m.p.145℃。
以一般公知的方法,例如本文中的方法(参见实施例Ⅱ-B-1),可以将实施例(ⅩⅩⅢ-B-1),(ⅩⅩⅢ-B-2)和(ⅩⅩⅩⅢ-B-3)的化合物转化成相应的酰氯化合物:
实施例(ⅩⅩ-B-2)
在0-5℃下,用大约5分钟,向60ml无水二甲基甲酰胺(DMF)中的9.8g(0.03mol)实施例(Ⅲ-2)化合物(纯度73%)中加入3.36g(0.03mol)叔丁醇钾,在该温度下继续搅拌1小时。然后将反应混合物加入180ml冰水中的8ml浓盐酸中并搅拌30分钟,吸滤出产物,用水洗涤,在40℃干燥。产率:7.0g,m.p.241.5℃。实施例(Ⅰ-B-2-a-2)
实施例(Ⅰ-B-2-b-1)
在10-15℃下,向30ml二氯甲烷中的2.24g(0.008mol)实施例(Ⅰ-B-2-a-1)化合物和1.0g(0.01mol)三乙胺中滴加5ml二氯甲烷中的1.18g(0.0088mol)2,2-二甲基丁酰氯,混合物在不冷却下搅拌过夜。加入30ml二氯甲烷,并且混合物连续用50ml水,50ml 10%强度的碳酸钠溶液和2×50ml水洗涤,干燥并浓缩。残余物在石油醚中搅拌,吸滤并干燥。产率:1.2g,m.p.110℃。实施例(Ⅲ-1)
5.38g实施例(ⅩⅩ-B-2)化合物和4.13g1-羟基环己基甲酸乙酯在140℃下共加热14小时,混合物用油泵浓缩并脱气。产率:8.3g,油状物。
不用进一步表征,该产物被转化成实施例(Ⅰ-B-2-a-2)化合物。实施例(Ⅲ-2)
类似于实施例(Ⅲ-1),或者根据对于制备式(Ⅲ)化合物给出的一般信息,获得下面的化合物:其不用进一步表征即可被直接转化成实施例(Ⅰ-B-2-a-1)化合物。应用实施例实施例1叶螨(Tetranychus)试验(OP抗性/喷雾处理)溶剂: 3份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
用期望浓度的活性化合物制剂喷雾被所有发育阶段的温室棉叶螨或棉叶螨(Tetranychus urticae)严重侵染的豆类植物(菜豆,Phaseolus vulgaris)。
经所期望的时间后,测定杀伤百分率。100%表示所有的叶螨都已经被杀死;0%表示没有叶螨被杀死。
在该项试验中,例如1000ppm试验活性化合物浓度的制备实施例(Ⅰ-B-1-a-1)的化合物在13天后显示出100%活性。实施例2叶蝉(Nephotettix)试验溶剂: 7份重量二甲基甲酰胺乳化剂: 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过将其浸入期望浓度的活性化合物制剂中来处理稻(稻,OryzaSativa)的籽苗,并且在叶子还湿润的时候感染黑尾叶蝉(Nephotettix cincticeps)。
经所期望的时间后,测定杀伤百分率。100%表示所有的叶蝉都已经被杀死;0%表示没有叶蝉被杀死。
在该项试验中,例如0.1%试验活性化合物浓度的制备实施例(Ⅰ-B-1-a-1),(Ⅰ-B-1-b-1)和(Ⅰ-B-1-c-1)的化合物在6天后显示出100%杀死率。
Claims (14)
1.式(Ⅰ)化合物
其中
A)V1代表氮原子,和
V2代表CH或C-Z,和
V3代表CY,或
B)V1代表CX,和
V2代表氮原子,和
V3代表CY,或
C)V1代表CX,和
V2代表CH或C-Z,和
V3代表氮原子,
并且其中
W代表氢,氰基,硝基,卤素,烷基,链烯基,炔烃基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代链烯基氧基,或者在各种情况下任选被取代的苯基,苯氧基,苯硫基,苯基烷氧基或苯基烷硫基,
X代表氢,卤素,烷基,链烯基,炔烃基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,卤代链烯基氧基,氰基,硝基,或者在各种情况下任选被取代的苯基,苯氧基,苯硫基,苯基烷氧基或苯基烷硫基,
Y代表氢,卤素,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,氰基或硝基,
Z代表卤素,烷基,烷氧基,烷硫基,卤代烷基,卤代烷氧基,羟基,氰基,硝基或者在各种情况下任选被取代的苯氧基,苯硫基,5-或6-元杂芳基氧基,5-或6-元杂芳基硫基,苯基烷基氧基或苯基烷硫基,或者
n代表1的情况下,Y和Z与它们所键连的碳原子一起代表任选插入杂原子的任选被取代的环,或者
n代表1的情况下,W和Z与它们所键连的紧邻的碳原子一起代表任选插入杂原子的任选被取代的环,
n代表0,1或在A)和C)的情况下也代表2,当n=2时,取代基Z可是相同或不同的,
Het代表下面基团之一:或
其中
A代表氢,或者代表烷基,链烯基,烷氧基烷基,多烷氧基烷基或烷硫基烷基,其中各基团任选被卤素取代,或者代表各种情况下饱和或不饱和的且任选被取代的环烷基或杂环基,或者代表芳基,芳基烷基或杂芳基,其中各基团任选被卤素,烷基,卤代烷基,烷氧基,卤代烷氧基,氰基或硝基取代,
B代表氢,烷基或烷氧基烷基,或者
A和B与它们所键连的碳原子一起代表饱和的或不饱和的,任选被取代的碳环或杂环,
D代表氢或者任选被取代的烷基,链烯基,炔烃基,烷氧基烷基,多烷氧基烷基,烷硫基烷基,饱和的或不饱和的环烷基,饱和的或不饱和的杂环基,芳基烷基,芳基,杂芳基烷基或杂芳基残基,或者
A和D与它们所键连的原子一起代表各种情况下任选被取代的碳环或杂环,
其中
E代表金属离子等价物或铵离子,
L代表氧或硫,
M代表氧或硫,
R1代表烷基,链烯基,烷氧基烷基,烷硫基烷基或多烷氧基烷基,其中各基团任选被卤素取代,或者代表环烷基或杂环基,其中各基团任选被卤素,烷基或烷氧基取代,或者代表各种情况下任选被取代的苯基,苯基烷基,杂芳基,苯氧基烷基或杂芳基氧基烷基,
R2代表烷基,链烯基,烷氧基烷基或多烷氧基烷基,其中各基团任选被卤素取代,或者代表各种情况下任选被取代的环烷基,苯基或苄基,
R3,R4和R5各自独立地代表烷基,烷氧基,烷基氨基,二烷基氨基,烷硫基,链烯基硫基或环烷基硫基,其中各基团任选被卤素取代,或者代表各种情况下任选被取代的苯基,苄基,苯氧基或苯硫基,
R6和R7各自独立地代表氢,或者代表烷基,环烷基,链烯基,烷氧基或烷氧基烷基,其中各基团任选被卤素取代,或者代表各种情况下任选被取代的苯基或苄基,或者与它们所键连的N原子一起形成任选包含氧原子或硫原子的任选被取代的环。
2.制备权利要求1的式(Ⅰ)化合物的方法,特征在于:
其中
A,B,W,V1,V2,V3,n和Z具有权利要求1给出的定义,并且
R8代表烷基,
进行分子内缩合反应时,得到式(Ⅰ-1-a)化合物
其中
A,B,W,V1,V2,V3,n和Z具有权利要求1给出的定义,
(B)当在稀释剂存在和在碱的存在下式(Ⅲ)化合物
其中
A,B,W,V1,V2,V3,n,Z和R8具有上述定义,
其中
A,B,W,V1,V2,V3,n和Z具有上述定义,
其中
A,B,W,V1,V2,V3,n,Z和R8具有上述定义,并且
T代表氢,卤素,烷基或烷氧基,
其中
A,B,W,V1,V2,V3,n和Z具有上述定义,
其中
A和D具有上述定义,
或者式(Ⅴa)的其甲硅烷基烯醇
其中
A和D具有上述定义,和
R8’代表烷基,
与式(Ⅵ)化合物反应时
其中
W,V1,V2,V3,n和Z具有上述定义,和
Hal代表卤素,
其中
A,D,W,V1,V2,V3,n和Z具有上述定义,
其中
A具有上述定义,
其中
Hal,W,V1,V2,V3,n和Z具有上述定义,
其中
A,W,V1,V2,V3,n和Z具有上述定义,并且
如果适当的话,随后使所得到的式(Ⅰ-1-a)到(Ⅰ-5-a)化合物分别
其中
R1具有权利要求1给出的定义,和
Hal代表卤素,
或者
β)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(Ⅸ)酸酐反应
R1-CO-O-CO-R1 (Ⅸ)
其中
R1具有上述定义,
(G)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(Ⅹ)氯甲酸酯或氯甲酸硫酯反应,
R2-M-CO-Cl (Ⅹ)
其中
R2和M具有权利要求1给出的定义,
其中
M和R2具有上述定义,
或者
β)如果适当在稀释剂存在下和如果适当在碱存在下,与二硫化碳反应并接着与式(Ⅻ)化合物反应
R2-Hal (Ⅻ)
其中
R2具有上述定义,
Hal代表氯,溴或碘,
或者
(Ⅰ)如果适当在稀释剂存在下和如果适当在酸结合剂存在下,与式(ⅩⅢ)磺酰氯反应,
R3-SO2-Cl (ⅩⅢ)
其中
R3具有权利要求1给出的定义,
或者
其中
L,R4和R5具有权利要求1给出的定义,且
Hal代表卤素,
或者
(K)如果适当在稀释剂存在下,与式(ⅩⅤ)或(ⅩⅥ)的金属化合物或胺反应,Me(OR10)t(ⅩⅤ)
其中
Me代表一价或二价金属,
t代表数1或2,并且
R10,R11和R12各自独立地代表氢或者烷基,
或者
(L)α)如果适当在稀释剂存在下和如果适当在催化剂存在下,与式(ⅩⅦ)异氰酸酯或异硫氰酸酯反应
R6-N=C=L (ⅩⅦ)
其中
R6和L具有权利要求1给出的定义,
或者
其中
L,R6和R7具有权利要求1给出的定义。
3.式(Ⅱ)化合物其中A,B,W,X,V1,V2,V3和n具有权利要求1给出的定义,并且R8代表烷基。
8.式(Ⅵ)化合物其中W,V1,V2,V3,n和Z具有权利要求1给出的定义,并且Hal代表氯或溴。
11.杀虫剂和除草剂,特征在于,其含有至少一种权利要求1的式(Ⅰ)化合物。
12.权利要求1的式(Ⅰ)化合物防治害虫和杂草的用途。
13.防治害虫和杂草的方法,特征在于,使权利要求1的式(Ⅰ)化合物分别作用于害虫和杂草,和/或其栖生地。
14.制备杀虫剂和除草剂组合物的方法,特征在于,将权利要求1的式(Ⅰ)化合物与扩充剂和/或表面活性剂混合。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114369082A (zh) * | 2022-02-28 | 2022-04-19 | 贵州大学 | 一种吡啶取代螺环类化合物及其制备方法和在制备抗植物病毒药剂中的应用 |
Families Citing this family (83)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6642261B2 (en) * | 1997-11-21 | 2003-11-04 | Athena Neurosciences, Inc. | N-(aryl/heteroarylacety) amino acid esters, pharmaceutical compositions comprising same, and methods for inhibiting β-amyloid peptide release and/or its synthesis by use of such compounds |
DE10007411A1 (de) * | 2000-02-18 | 2001-08-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10013914A1 (de) | 2000-03-21 | 2001-09-27 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10015310A1 (de) * | 2000-03-28 | 2001-10-04 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
DE10017881A1 (de) * | 2000-04-11 | 2001-10-25 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10018370A1 (de) * | 2000-04-14 | 2001-10-18 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10029077A1 (de) * | 2000-06-13 | 2001-12-20 | Bayer Ag | Thiazolylsubstituierte Heterocyclen |
AR029677A1 (es) | 2000-06-29 | 2003-07-10 | Bayer Ag | Combinaciones de compuestos activos con propiedades insecticidas y acaricidas |
DE10042736A1 (de) | 2000-08-31 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10043610A1 (de) * | 2000-09-05 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10055941A1 (de) | 2000-11-10 | 2002-05-23 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10062422A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Ag | Verwendung von Acetyl-CoA Carboxylase zum Identifizieren von insektizid wirksamen Verwendung |
US7842727B2 (en) | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
DE10139465A1 (de) * | 2001-08-10 | 2003-02-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten, cayclischen Ketoenolen und Safenern |
AU2003243272A1 (en) | 2002-05-22 | 2003-12-12 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-ketoepoxide compounds |
CA2486402C (en) * | 2002-05-22 | 2013-04-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on alpha-chalcogenmethylcarbonyl compounds |
DE10301804A1 (de) * | 2003-01-20 | 2004-07-29 | Bayer Cropscience Ag | 2,4-Dihalogen-6-(C2-C3-alkyl)-phenyl substituierte Tetramsäure-Derivate |
DE10311300A1 (de) | 2003-03-14 | 2004-09-23 | Bayer Cropscience Ag | 2,4,6-Phenylsubstituierte cyclische Ketoenole |
DE10326386A1 (de) | 2003-06-12 | 2004-12-30 | Bayer Cropscience Ag | N-Heterocyclyl-phenylsubstituierte cyclische Ketoenole |
DE10330724A1 (de) | 2003-07-08 | 2005-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE10354628A1 (de) | 2003-11-22 | 2005-06-16 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl-substituierte Tetramsäure-Derivate |
DE10354629A1 (de) | 2003-11-22 | 2005-06-30 | Bayer Cropscience Ag | 2-Ethyl-4,6-dimethyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
AU2004294259C1 (en) * | 2003-12-04 | 2014-07-10 | Bayer Cropscience Aktiengesellschaft | Active substance combination having insecticidal and acaricidal properties |
DE102004014620A1 (de) | 2004-03-25 | 2005-10-06 | Bayer Cropscience Ag | 2,4,6-phenylsubstituierte cyclische Ketoenole |
DE102004035133A1 (de) * | 2004-07-20 | 2006-02-16 | Bayer Cropscience Ag | Selektive Insektizide auf Basis von substituierten, cyclischen Ketoenolen und Safenern |
DE102004044827A1 (de) | 2004-09-16 | 2006-03-23 | Bayer Cropscience Ag | Jod-phenylsubstituierte cyclische Ketoenole |
DE102004053191A1 (de) * | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2,6-Diethyl-4-methyl-phenyl substituierte Tetramsäure-Derivate |
DE102004053192A1 (de) | 2004-11-04 | 2006-05-11 | Bayer Cropscience Ag | 2-Alkoxy-6-alkyl-phenyl substituierte spirocyclische Tetramsäure-Derivate |
DE102005003076A1 (de) * | 2005-01-22 | 2006-07-27 | Bayer Cropscience Ag | Verwendung von Tetramsäurederivaten zur Bekämpfung von Insekten aus der Gattung der Pflanzenläuse (Sternorrhyncha) |
DE102005008021A1 (de) * | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Spiroketal-substituierte cyclische Ketoenole |
DE102005008033A1 (de) * | 2005-02-22 | 2006-08-24 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102005059469A1 (de) * | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
DE102006014653A1 (de) * | 2006-03-28 | 2007-10-04 | Bayer Cropscience Ag | Verwendung von Tetramsäurederivaten zur Bekämpfung von Insekten durch Angiessen, Tröpfchenapplikation oder Bodeninjektion |
DE102006018828A1 (de) | 2006-04-22 | 2007-10-25 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
DE102006022821A1 (de) | 2006-05-12 | 2007-11-15 | Bayer Cropscience Ag | Verwendung von Tetramsäurederivaten zur Bekämpfung von Insekten aus der Ordnung der Käfer (Coleoptera), Thrips (Tysanoptera), Wanzen (Hemiptera), Fliegen (Diptera) und Zikaden (Auchenorrhynchae) |
DE102006025874A1 (de) * | 2006-06-02 | 2007-12-06 | Bayer Cropscience Ag | Alkoxyalkyl-substituierte cyclische Ketoenole |
DE102006027730A1 (de) * | 2006-06-16 | 2007-12-20 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006027732A1 (de) | 2006-06-16 | 2008-01-10 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006027731A1 (de) | 2006-06-16 | 2007-12-20 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006033154A1 (de) | 2006-07-18 | 2008-01-24 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
DE102006050148A1 (de) | 2006-10-25 | 2008-04-30 | Bayer Cropscience Ag | Trifluormethoxy-phenylsubstituierte Tetramsäure-Derivate |
DE102006057037A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | cis-Alkoxyspirocyclische biphenylsubstituierte Tetramsäure-Derivate |
DE102006057036A1 (de) | 2006-12-04 | 2008-06-05 | Bayer Cropscience Ag | Biphenylsubstituierte spirocyclische Ketoenole |
DE102007009957A1 (de) * | 2006-12-27 | 2008-07-03 | Bayer Cropscience Ag | Verfahren zur verbesserten Nutzung des Produktionsptentials transgener Pflanzen |
US20080259134A1 (en) * | 2007-04-20 | 2008-10-23 | Hewlett-Packard Development Company Lp | Print head laminate |
EP2014169A1 (de) | 2007-07-09 | 2009-01-14 | Bayer CropScience AG | Wasserlösliche Konzentrate von 3-(2-Alkoxy-4-chlor-6-alkyl-phenyl)-substituierten Tetramaten und ihren korrespondierenden Enolen |
EP2020413A1 (de) | 2007-08-02 | 2009-02-04 | Bayer CropScience AG | Oxaspirocyclische-spiro-substituierte Tetram- und Tetronsäure-Derivate |
GB0717082D0 (en) * | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2045240A1 (de) | 2007-09-25 | 2009-04-08 | Bayer CropScience AG | Halogenalkoxyspirocyclische Tetram- und Tetronsäure-Derivate |
EP2103615A1 (de) | 2008-03-19 | 2009-09-23 | Bayer CropScience AG | 4'4'-Dioxaspiro-spirocyclisch substituierte Tetramate |
US8404260B2 (en) | 2008-04-02 | 2013-03-26 | Bayer Cropscience Lp | Synergistic pesticide compositions |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
TW201031327A (en) | 2008-11-14 | 2010-09-01 | Bayer Cropscience Ag | Active compound combinations having insecticidal and acaricidal properties |
US8389443B2 (en) * | 2008-12-02 | 2013-03-05 | Bayer Cropscience Ag | Geminal alkoxy/alkylspirocyclic substituted tetramate derivatives |
US8846946B2 (en) | 2008-12-02 | 2014-09-30 | Bayer Cropscience Ag | Germinal alkoxy/alkylspirocyclic substituted tetramate derivatives |
AR075126A1 (es) | 2009-01-29 | 2011-03-09 | Bayer Cropscience Ag | Metodo para el mejor uso del potencial de produccion de plantas transgenicas |
CN103641709B (zh) | 2009-03-11 | 2017-08-25 | 拜耳知识产权有限责任公司 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
DE102009028001A1 (de) | 2009-07-24 | 2011-01-27 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
BR112012020084B1 (pt) | 2010-02-10 | 2017-12-19 | Bayer Intellectual Property Gmbh | A process for the preparation of pesticides and / or herbicides and / or fungi and / or fungi and / or fungicides and / or fungicides and / or fungicides and / or fungicides. METHOD FOR INCREASING THE ACTION OF PESTICIDES AND / OR HERBICIDES AND / OR FUNGICIDES COMPREHENDING SUCH COMPOUNDS |
ES2545113T3 (es) * | 2010-02-10 | 2015-09-08 | Bayer Intellectual Property Gmbh | Derivados de ácido tetrámico sustituidos de manera espiroheterocíclica |
DE102010008643A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
DE102010008642A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
WO2011131623A1 (de) | 2010-04-20 | 2011-10-27 | Bayer Cropscience Ag | Insektizide und/oder herbizide zusammensetzung mit verbesserter wirkung auf basis von spiroheterocyclisch-substituierten tetramsäure-derivaten |
BR112013018973A2 (pt) | 2011-01-25 | 2017-09-19 | Bayer Ip Gmbh | processo para a preparação de derivados de 1-h-pirrolidina-2,4-diona |
DE102011011040A1 (de) | 2011-02-08 | 2012-08-09 | Bayer Pharma Aktiengesellschaft | (5s,8s)-3-(4'-Chlor-3'-fluor-4-methylbiphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro[4.5]dec-3-en-2-on (Verbindung A) zur Therapie |
US9000026B2 (en) | 2011-02-17 | 2015-04-07 | Bayer Intellectual Property Gmbh | Substituted 3-(biphenyl-3-yl)-8,8-difluoro-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-ones for therapy |
DE102011080405A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-8,8-difluor-4-hydroxy-1-azaspiro[4.5]dec-3-en-2-one zur Therapie |
CA2828639C (en) | 2011-03-01 | 2019-02-12 | Bayer Intellectual Property Gmbh | 2-acyloxypyrrolin-4-ones |
DE102011080406A1 (de) | 2011-08-04 | 2013-02-07 | Bayer Pharma AG | Substituierte 3-(Biphenyl-3-yl)-4-hydroxy-8-methoxy-1-azaspiro8[4.5]dec-3-en-2-one |
EP2742030B1 (de) | 2011-08-11 | 2016-07-27 | Bayer Intellectual Property GmbH | 1,2,4-triazolyl-substituierte ketoenole zum einsatz im pflanzenschutz |
DK2806741T3 (da) | 2012-01-26 | 2020-05-18 | Bayer Ip Gmbh | Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter |
US10519085B2 (en) | 2016-01-15 | 2019-12-31 | Bayer Cropscience Aktiengesellschaft | Process for preparing substituted 2-arylethanols |
WO2019197617A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von tierischen schädlingen durch angiessen, tröpfchenapplikation. pflanzlochbehandlung oder furchenapplikation |
AU2019250592A1 (en) | 2018-04-13 | 2020-10-22 | Bayer Aktiengesellschaft | Use of tetramic acid derivatives for controlling pests by watering or droplet application |
JP2021521151A (ja) | 2018-04-13 | 2021-08-26 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 特定の昆虫を防除するためのテトラミン酸誘導体の使用 |
WO2019197652A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Aktiengesellschaft | Feststoff-formulierung insektizider mischungen |
WO2019197620A1 (de) | 2018-04-13 | 2019-10-17 | Bayer Cropscience Aktiengesellschaft | Verwendung von tetramsäurederivaten zur bekämpfung von speziellen insekten |
WO2022072746A1 (en) | 2020-09-30 | 2022-04-07 | Control Solutions, Inc. | Powder pest control compositions and methods of using |
BR112023017783A2 (pt) | 2021-03-01 | 2023-11-21 | Control Solutions Inc | Métodos e composições de controle de pragas em partículas sólidas |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3542809A (en) * | 1968-10-23 | 1970-11-24 | Pfizer | Synthesis of arylchlorocarbonyl ketenes |
US4678501A (en) * | 1981-07-30 | 1987-07-07 | Union Carbide Corporation | Certain pyrazinyl 1,3 cycloalkanedione derivatives having herbicidal activity |
DE3314249A1 (de) * | 1983-04-20 | 1984-10-25 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von fluorierten phenylessigsaeureestern und neue fluorierte trichlorethylbenzole |
US4837204A (en) * | 1985-01-23 | 1989-06-06 | Abbott Laboratories | Functionalized peptidyl aminodiols and -triols |
NZ218937A (en) * | 1986-01-16 | 1990-03-27 | Abbott Lab | Functionalised peptidyl aminodiols and -triols as renin inhibitors and pharmaceutical compositions |
US5142065A (en) * | 1988-08-20 | 1992-08-25 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-diones |
DE3913682A1 (de) * | 1989-04-26 | 1990-10-31 | Bayer Ag | 3-aryl-pyrrolidin-2,4-dione |
US4985063A (en) * | 1988-08-20 | 1991-01-15 | Bayer Aktiengesellschaft | 3-aryl-pyrrolidine-2,4-diones |
US5186737A (en) * | 1989-01-07 | 1993-02-16 | Bayer Aktiengesellschaft | Pesticidal 3-aryl-pyrrolidine-2,4-diones |
DE3929087A1 (de) * | 1989-09-01 | 1991-03-07 | Bayer Ag | 3-aryl-pyrrolidin-2,4-dion-derivate |
DE4014420A1 (de) * | 1989-09-23 | 1991-04-04 | Bayer Ag | 5h-furan-2-on-derivate |
US5207817A (en) * | 1989-09-23 | 1993-05-04 | Bayer Aktiengesellschaft | Herbicidal 5H-furan-2-one derivatives |
DE4032090A1 (de) * | 1990-02-13 | 1991-08-14 | Bayer Ag | Polycyclische 3-aryl-pyrrolidin-2,4-dion-derivate |
DE4107394A1 (de) * | 1990-05-10 | 1991-11-14 | Bayer Ag | 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
WO1992016510A1 (en) * | 1991-03-19 | 1992-10-01 | Ciba-Geigy Ag | Novel herbicidally, acaricidally and insecticidally active compounds |
DE4121365A1 (de) * | 1991-06-28 | 1993-01-14 | Bayer Ag | Substituierte 1-h-3-aryl-pyrrolidin-2,4-dion-derivate |
DK0521827T3 (da) * | 1991-07-03 | 1996-11-11 | Ciba Geigy Ag | Farmakologisk virksomme hydrazinderivater og fremgangsmåde til deres fremstilling |
DE4216814A1 (de) * | 1991-07-16 | 1993-01-21 | Bayer Ag | 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrofuranon- und 3-aryl-4-hydroxy-(delta)(pfeil hoch)3(pfeil hoch)-dihydrothiophenon-derivate |
EP0652700A1 (en) * | 1992-07-28 | 1995-05-17 | Kverneland Underhaug A/S | Bale wrapper apparatus |
AU666040B2 (en) * | 1992-10-28 | 1996-01-25 | Bayer Aktiengesellschaft | Substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives |
DE4243818A1 (de) * | 1992-12-23 | 1994-06-30 | Bayer Ag | 5-Aryl-1,3-thiazin-Derivate |
DE4306257A1 (de) * | 1993-03-01 | 1994-09-08 | Bayer Ag | Substituierte 1-H-3-Phenyl-5-cycloalkylpyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung |
DE4306259A1 (de) * | 1993-03-01 | 1994-09-08 | Bayer Ag | Dialkyl-1-H-3-(2,4-dimethylphenyl)-pyrrolidin-2,4-dione, ihre Herstellung und ihre Verwendung |
WO1994029268A1 (de) * | 1993-06-07 | 1994-12-22 | Bayer Aktiengesellschaft | Iodpropargylcarbamate und ihre verwendung als biozide im pflanzen- und materialschutz |
US5981567A (en) * | 1993-07-02 | 1999-11-09 | Bayer Aktiengesellschaft | Substituted spiroheterocyclic 1h-3-aryl-pyrrolidine-2,4-dione derivatives and their use as pesticides |
AU7159994A (en) * | 1993-09-17 | 1995-03-30 | Bayer Aktiengesellschaft | 3-aryl-4-hydroxy-delta3-dihydrofuranone derivatives |
DE4425617A1 (de) * | 1994-01-28 | 1995-08-03 | Bayer Ag | 1-H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
DE4431730A1 (de) * | 1994-02-09 | 1995-08-10 | Bayer Ag | Substituierte 1H-3-Aryl-pyrrolidin-2,4-dion-Derivate |
DE4410420A1 (de) * | 1994-03-25 | 1995-09-28 | Bayer Ag | 3-Aryl-4-hydroxy- DELTA·3·-dihydrothiophenon-Derivate |
BR9507275A (pt) * | 1994-04-05 | 1997-11-18 | Bayer Ag | 1h-3-aril-pirrolidina-2,4-dionas alcoxi-alquil-substituídas |
-
1997
- 1997-04-28 CN CNB971962936A patent/CN1156470C/zh not_active Expired - Fee Related
- 1997-04-28 BR BR9708989A patent/BR9708989A/pt not_active IP Right Cessation
- 1997-04-28 WO PCT/EP1997/002183 patent/WO1997043275A2/de active IP Right Grant
- 1997-04-28 AU AU27733/97A patent/AU2773397A/en not_active Abandoned
- 1997-04-28 JP JP54044297A patent/JP4306799B2/ja not_active Expired - Fee Related
- 1997-04-28 EP EP97921808A patent/EP0912547B1/de not_active Expired - Lifetime
- 1997-04-28 ES ES97921808T patent/ES2251022T3/es not_active Expired - Lifetime
- 1997-04-28 US US09/180,118 patent/US6133296A/en not_active Expired - Lifetime
- 1997-04-28 DE DE59712444T patent/DE59712444D1/de not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114369082A (zh) * | 2022-02-28 | 2022-04-19 | 贵州大学 | 一种吡啶取代螺环类化合物及其制备方法和在制备抗植物病毒药剂中的应用 |
CN114369082B (zh) * | 2022-02-28 | 2023-09-05 | 贵州大学 | 吡啶取代螺环类化合物及其在制备抗植物病毒剂中的应用 |
Also Published As
Publication number | Publication date |
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JP2000513715A (ja) | 2000-10-17 |
JP4306799B2 (ja) | 2009-08-05 |
DE59712444D1 (de) | 2006-02-23 |
CN1156470C (zh) | 2004-07-07 |
AU2773397A (en) | 1997-12-05 |
BR9708989A (pt) | 1999-08-03 |
WO1997043275A2 (de) | 1997-11-20 |
WO1997043275A3 (de) | 1998-01-08 |
EP0912547A2 (de) | 1999-05-06 |
ES2251022T3 (es) | 2006-04-16 |
US6133296A (en) | 2000-10-17 |
EP0912547B1 (de) | 2005-10-12 |
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