CN1280271C - 芳基苯基-取代的环状酮烯醇类化合物 - Google Patents
芳基苯基-取代的环状酮烯醇类化合物 Download PDFInfo
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- CN1280271C CN1280271C CNB998055204A CN99805520A CN1280271C CN 1280271 C CN1280271 C CN 1280271C CN B998055204 A CNB998055204 A CN B998055204A CN 99805520 A CN99805520 A CN 99805520A CN 1280271 C CN1280271 C CN 1280271C
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- 125000004122 cyclic group Chemical class 0.000 title abstract description 5
- -1 phenoxy, phenylthio Chemical group 0.000 claims abstract description 417
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 83
- 239000001257 hydrogen Substances 0.000 claims abstract description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 78
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 62
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 58
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 51
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 40
- 150000002367 halogens Chemical group 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 289
- 238000000034 method Methods 0.000 claims description 206
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 118
- 229910052760 oxygen Inorganic materials 0.000 claims description 96
- 239000001301 oxygen Substances 0.000 claims description 94
- 238000006243 chemical reaction Methods 0.000 claims description 90
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 80
- 239000002253 acid Substances 0.000 claims description 77
- 239000005864 Sulphur Substances 0.000 claims description 76
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 75
- 239000000460 chlorine Chemical group 0.000 claims description 68
- 238000002360 preparation method Methods 0.000 claims description 68
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 50
- 239000002585 base Substances 0.000 claims description 49
- 239000011737 fluorine Substances 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- 239000003513 alkali Substances 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 41
- 125000004429 atom Chemical group 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 37
- 229910052794 bromium Inorganic materials 0.000 claims description 37
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 36
- 239000011230 binding agent Substances 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 27
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 23
- 125000001544 thienyl group Chemical group 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 241000238631 Hexapoda Species 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 10
- 230000005494 condensation Effects 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000011574 phosphorus Substances 0.000 claims description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 238000006073 displacement reaction Methods 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 150000001266 acyl halides Chemical class 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229910021645 metal ion Inorganic materials 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000013543 active substance Substances 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 5
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 230000002508 compound effect Effects 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000002228 disulfide group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 10
- 238000009361 aviculture Methods 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 8
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- 125000004660 phenylalkylthio group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 93
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 56
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 38
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
- 239000003999 initiator Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 241000196324 Embryophyta Species 0.000 description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- 239000000463 material Substances 0.000 description 28
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
- 150000003851 azoles Chemical class 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 235000017550 sodium carbonate Nutrition 0.000 description 19
- 229910000029 sodium carbonate Inorganic materials 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000370 acceptor Substances 0.000 description 17
- 239000003085 diluting agent Substances 0.000 description 17
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 17
- 235000015320 potassium carbonate Nutrition 0.000 description 17
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 17
- 150000003818 basic metals Chemical class 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 150000002170 ethers Chemical class 0.000 description 16
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 16
- 229910052728 basic metal Inorganic materials 0.000 description 15
- 239000003995 emulsifying agent Substances 0.000 description 15
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- 229910052708 sodium Inorganic materials 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 244000025254 Cannabis sativa Species 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 238000007429 general method Methods 0.000 description 13
- 150000004702 methyl esters Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 description 11
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 229960003424 phenylacetic acid Drugs 0.000 description 11
- 239000003279 phenylacetic acid Substances 0.000 description 11
- 239000002798 polar solvent Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000003444 phase transfer catalyst Substances 0.000 description 10
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 238000009333 weeding Methods 0.000 description 10
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 9
- 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 9
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 241000209140 Triticum Species 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000012973 diazabicyclooctane Substances 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 229910052500 inorganic mineral Inorganic materials 0.000 description 9
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- VZAWCLCJGSBATP-UHFFFAOYSA-N 1-cycloundecyl-1,2-diazacycloundecane Chemical compound C1CCCCCCCCCC1N1NCCCCCCCCC1 VZAWCLCJGSBATP-UHFFFAOYSA-N 0.000 description 8
- 241001124076 Aphididae Species 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
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- 235000007164 Oryza sativa Nutrition 0.000 description 8
- 241001674048 Phthiraptera Species 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 230000000895 acaricidal effect Effects 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
- 150000004820 halides Chemical class 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 8
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002023 wood Substances 0.000 description 8
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 7
- 150000001336 alkenes Chemical class 0.000 description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 7
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 7
- 239000000292 calcium oxide Substances 0.000 description 7
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
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- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
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- 210000002268 wool Anatomy 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/47—Toluidines; Homologues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/52—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/61—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
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Abstract
Description
A | B | D |
CH3 | H | H |
C2H5 | H | H |
C3H7 | H | H |
i-C3H7 | H | H |
C4H9 | H | H |
i-C4H9 | H | H |
s-C4H9 | H | H |
t-C4H9 | H | H |
CH3 | CH3 | H |
C2H5 | CH3 | H |
C3H7 | CH3 | H |
i-C3H7 | CH3 | H |
C4H9 | CH3 | H |
i-C4H9 | CH3 | H |
s-C4H9 | CH3 | H |
t-C4H9 | CH3 | H |
A | D | B |
-(CH2)3- | H | |
-(CH2)4- | H | |
-CH2-CHCH3-CH2- | H | |
-CH2-CH2-CHCH3- | H | |
-CH2-CHCH3-CHCH3- | H | |
-CH2-S-CH2- | H | |
-CH2-S-(CH2)2- | H | |
-(CH2)2-S-CH2- | 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 |
活性成分克数/公顷 | 糖甜菜 | 野燕麦 | 狗尾草 | 芥草 | |
实施例I-1-a-2 | 250 | 20 | 70 | 100 | 70 |
活性成分克数/公顷 | 野燕麦 | 狗尾草 | 苘麻 | 苋草 | |
实施例I-1-a-4 | 250 | 90 | 100 | 80 | 80 |
活性成分克数/公顷 | 看麦娘 | 狗尾草 | 苋草 | 猪殃殃 | |
实施例I-1-a-3 | 250 | 100 | 100 | 100 | 90 |
实施例序号 | X | Z | V1 | V2 | D | A | B | m.p.℃ | 异构体 |
I-1-a-2 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | >240 | β | |
I-1-a-3 | CH3 | Cl | 4-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | 211 | β | |
I-1-a-4 | CH3 | Cl | 4-Cl | H | H | -(CH2)2-CHOC2H5-(CH2)2- | >230 | β | |
I-1-a-5 | CH3 | CH3 | 4-Cl | H | H | -CH2-O-(CH2)3- | >240 | - | |
I-1-a-6 | C2H5 | CH3 | 4-Cl | H | H | CH3 | CH3 | >240 | - |
I-1-a-7 | C2H5 | C2H5 | 4-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | 188 | β | |
I-1-a-8 | CH3 | Cl | 4-Cl | H | H | -(CH2)2-O-(CH2)2- | 165-167 | - | |
I-1-a-9 | C2H5 | Cl | 4-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | >240 | β | |
I-1-a-10 | C2H5 | Cl | 4-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | >240 | β | |
I-1-a-11 | CH3 | Cl | 4-Cl | H | H | i-C3H7 | CH3 | >240 | - |
I-1-a-12 | CH3 | CH3 | 4-Cl | H | H | CH3 | CH3 | >240 | - |
I-1-a-13 | C2H5 | C2H5 | 4-Cl | H | H | i-C3H7 | CH3 | 218 | - |
I-1-a-14 | CH3 | CH3 | 4-Cl | H | H | -(CH2)5- | >240 | - | |
I-1-a-15 | CH3 | CH3 | 3-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | 135 | β | |
I-1-a-16 | CH3 | CH3 | 2-Cl | H | H | -(CH2)2CHOCH3(CH2)2- | >245 | β | |
I-1-a-17 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-O-(CH2)2- | >235 | - | |
I-1-a-18 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2CHOC2H5(CH2)2- | >245 | β | |
I-1-a-19 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | >245 | β | |
I-1-a-20 | CH3 | CH3 | 4-Cl | H | H | -CH2-CHCH3-(CH2)3- | >245 | β | |
I-1-a-21 | CH3 | CH3 | 4-Cl | H | -(CH2)4- | H | >240 | - | |
I-1-a-22 | CH3 | CH3 | 4-Cl | H | i-C3H7 | H | H | >249 | - |
I-1-a-23 | CH3 | CH3 | 2-CH3 | 5-CH3 | H | -CH2-O-(CH2)3- | 148 | - | |
I-1-a-24 | CH3 | CH3 | 2-CH3 | 6-CH3 | H | -CH2-O-(CH2)3- | >250 | - | |
I-1-a-25 | CH3 | CH3 | 3-CH3 | 5-CH3 | H | -CH2-O-(CH2)3- | >250 | - | |
I-1-a-26 | CH3 | Cl | 4-Cl | H | H | -(CH2)5- | >250 | - | |
I-1-a-27 | CH3 | Cl | 3-CF3 | 5-CF3 | H | -(CH2)5- | >250 | - | |
I-1-a-28 | CH3 | Cl | 4-CF3 | H | H | -(CH2)5- | >250 | - | |
I-1-a-29 | CH3 | Cl | 2-Cl | 4-Cl | H | -(CH2)5- | >250 | - | |
I-1-a-30 | CH3 | Cl | 3-Cl | 5-Cl | H | -(CH2)5- | >250 | - | |
I-1-a-31 | C2H5 | C2H5 | 4-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | >250 | - | |
I-1-a-32 | C2H5 | C2H5 | 3-CF3 | 5-CF3 | H | -(CH2)2CHCH3-(CH2)2- | 242-244 | β |
实施例序号 | X | Z | V1 | V2 | D | A | B | m.p.℃ | 异构体 |
I-1-a-33 | C2H5 | C2H5 | 4-CF3 | H | H | -(CH2)2CHCH3-(CH2)2- | >250 | β | |
I-1-a-34 | CH3 | CH3 | 4-Cl | H | H | i-C3H7 | CH3 | Wax | - |
I-1-a-35 | C2H5 | C2h5 | 2-Cl | 4-Cl | H | -(CH2)2CHCH3-(CH2)2- | >250 | β | |
I-1-a-36 | C2H5 | C2H5 | 3-Cl | 5-Cl | H | -(CH2)2CHCH3-(CH2)2- | >250 | β | |
I-1-a-37 | CH3 | CH3 | 2-Cl | 4-Cl | H | i-C3H7 | CH3 | 115-117 | - |
I-1-a-38 | CH3 | CH3 | 3-Cl | 5-Cl | H | i-C3H7 | CH3 | 233-234 | - |
I-1-a-39 | C2H5 | Cl | 4-Cl | H | H | CH3 | CH3 | >250 | - |
I-1-a-40 | C2H5 | Cl | 3-Cl | 5-Cl | H | CH3 | CH3 | 125-127 | - |
I-1-a-41 | CH3 | Cl | 4-Cl | H | H | CH3 | CH3 | >250 | - |
I-1-a-42 | CH3 | Cl | 3-CF3 | 5-CF3 | H | CH3 | CH3 | >250 | - |
I-1-a-43 | CH3 | CH3 | 4-Cl | H | H | i-C3H7 | CH3 | >250 | - |
I-1-a-44 | CH3 | CH3 | 4-CH3 | H | H | -(CH2)2-CHOCH3-(CH2)2- | >235 | β | |
I-1-a-45 | CH3 | CH3 | 2-CH3 | 5-F | H | -(CH2)2-CHOCH3-(CH2)2- | >235 | β | |
I-1-a-46 | CH3 | CH3 | 2-CH3 | 5-CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | 168 | β | |
I-1-a-47 | CH3 | CH3 | 2-OCH3 | H | H | -(CH2)2-CHOCH3-(CH2)2- | β | ||
I-1-a-48 | CH3 | CH3 | 3-CH3 | 5-CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | 238 | β | |
I-1-a-49 | CH3 | CH3 | 2-Cl | 4-Cl | H | -(CH2)2-CHOCH3-(CH2)2- | 188 | β | |
I-1-a-50 | CH3 | CH3 | 2-Cl | 3-Cl | H | -(CH2)2-CHOCH3-(CH2)2- | >235 | β |
实施例序号 | X | Z | V1 | V2 | A | B | R1 | m.p.℃ |
I-2-b-2 | CH3 | CH3 | 4-Cl | H | -(CH2)4- | i-C3H7- | 油状物 | |
I-2-b-3 | CH3 | CH3 | 4-Cl | H | -(CH2)5- | i-C3H7- | 油状物 | |
I-2-b-4 | CH3 | CH3 | 4-Cl | H | -CH2-CHCH3-(CH2)3- | i-C3H7- | 油状物 | |
I-2-b-5 | CH3 | CH3 | 4-Cl | H | -(CH2)2-CHCH3-(CH2)2- | i-C3H7- | 油状物 | |
I-2-b-6 | CH3 | CH3 | 4-Cl | H | -CH2-O-(CH2)3- | i-C3H7- | 油状物 | |
I-2-b-7 | CH3 | CH3 | 4-Cl | H | -(CH2)2-O-(CH2)2- | i-C3H7- | 油状物 | |
I-2-b-8 | CH3 | CH3 | 4-Cl | H | -CH2-CHCH3-O-(CH2)2- | i-C3H7- | 油状物 | |
I-2-b-9 | CH3 | CH3 | 4-Cl | H | -(CH2)2-CHOC2H5-(CH2)2- | i-C3H7- | 油状物 |
实施例序号 | X | Z | V1 | V2 | B | A | Q1 | Q2 | m.p.℃ |
I-7-a-3 | CH3 | CH3 | 3-Cl | H | -(CH2)5 | H | H | >250 | |
I-7-a-4 | CH3 | CH3 | 4-Cl | H | H | -(CH2)4- | H | >250 | |
I-7-a-5 | CH3 | CH3 | 3-Cl | H | H | -(CH2)4- | H | 211-213 | |
I-7-a-6 | CH3 | CH3 | 4-Cl | H | -(CH2)3-CHCH3-CH2- | H | H | 243-244 | |
I-7-a-7 | CH3 | CH3 | 3-Cl | H | -(CH2)3-CHCH3-CH2- | H | H | 蜡状物 |
实施例序号 | X | Z | V1 | V2 | B | A | Q1 | Q2 | R1 | m.p.℃ |
I-7-b-3 | CH3 | CH3 | 4-Cl | H | -(CH2)5- | H | H | i-C4H9 | 油状物 |
实施例序号 | X | Z | V1 | V2 | D | A | B | R8 | m.p.℃ | 异构体 |
II-3 | CH3 | CH3 | 3-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 88 | β | |
II-4 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 127 | β | |
II-5 | CH3 | CH3 | 2-Cl | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 75 | β | |
II-6 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-O-(CH2)2- | CH3 | 179 | - | |
II-7 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-OCHC2H5-(CH2)2- | CH3 | 146 | β | |
II-8 | CH3 | CH3 | 4-Cl | H | H | -(CH2)2-CHCH3-(CH2)2- | CH3 | 167 | β | |
II-9 | CH3 | CH3 | 4-CH3 | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 159 | β | |
II-10 | CH3 | CH3 | 2-CH3 | 5-F | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 138 | β | |
II-11 | CH3 | CH3 | 2-CH3 | 5-CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 71 | β | |
II-12 | CH3 | CH3 | 2-CH3 | 3-CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 133 | β | |
II-13 | CH3 | CH3 | 2-OCH3 | H | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 156 | β | |
II-14 | CH3 | CH3 | 3-CH3 | 5-CH3 | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 169 | β | |
II-15 | CH3 | CH3 | 2-Cl | 4-Cl | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 125 | β | |
II-16 | CH3 | CH3 | 2-Cl | 3-Cl | H | -(CH2)2-CHOCH3-(CH2)2- | CH3 | 127 | β | |
II-17 | CH3 | CH3 | 4-Cl | H | -(CH2)4- | H | C2H5 | oil | - | |
II-18 | CH3 | CH3 | 4-Cl | H | -(CH2)2-S-CH2- | H | C2H5 | 81 | - | |
II-19 | CH3 | CH3 | 4-Cl | H | i-C3H7 | H | H | C2H5 | 119 | - |
实施例序号 | X | Z | V1 | V2 | m.p.℃ |
XXIV-2 | CH3 | CH3 | 3-Cl | H | * |
XXIV-3 | CH3 | CH3 | 2-Cl | H | * |
XXIV-4 | CH3 | CH3 | 4-CH3 | H | * |
XXIV-5 | CH3 | CH3 | 2-CH3 | 5-F | * |
XXIV-6 | CH3 | CH3 | 2-CH3 | 5-CH3 | * |
XXIV-7 | CH3 | CH3 | 2-CH3 | 3-CH3 | * |
XXIV-8 | CH3 | CH3 | 2-OCH3 | H | * |
XXIV-9 | CH3 | CH3 | 3-CH3 | 5-CH3 | * |
XXIV-10 | CH3 | CH3 | 2-Cl | 4-Cl | * |
XXIV-11 | CH3 | CH3 | 2-Cl | 3-Cl | * |
实施例序号 | X | Z | V1 | V2 | m.p.℃ |
XXVII-2 | CH3 | CH3 | 3-Cl | H | 143 |
XXVII-3 | CH3 | CH3 | 2-Cl | H | 129 |
XXVII-4 | CH3 | CH3 | 4-CH3 | H | 154 |
XXVII-5 | CH3 | CH3 | 2-CH3 | 5-F | 120 |
XXVII-6 | CH3 | CH3 | 2-CH3 | 5-CH3 | 141 |
XXVII-7 | CH3 | CH3 | 2-CH3 | 3-CH3 | 155 |
XXVII-8 | CH3 | CH3 | 2-OCH3 | H | 151 |
XXVII-9 | CH3 | CH3 | 3-CH3 | 5-CH3 | 173 |
XXVII-10 | CH3 | CH3 | 2-Cl | 4-Cl | 166 |
XXVII-11 | CH3 | CH3 | 2-Cl | 3-Cl | 158 |
实施例序号 | X | Z | V1 | V2 | R8 | m.p.℃ |
XXXII-2 | CH3 | CH3 | 3-Cl | H | CH3 | 56 |
XXXII-3 | CH3 | CH3 | 2-Cl | H | CH3 | 油状物 |
XXXII-4 | CH3 | CH3 | 4-CH3 | H | CH3 | 137 |
XXXII-5 | CH3 | CH3 | 2-CH3 | 5-F | CH3 | 油状物 |
XXXII-6 | CH3 | CH3 | 2-CH3 | 5-CH3 | CH3 | 油状物 |
XXXII-7 | CH3 | CH3 | 2-CH3 | 3-CH3 | CH3 | 油状物 |
XXXII-8 | CH3 | CH3 | 2-OCH3 | H | CH3 | 85 |
XXXII-9 | CH3 | CH3 | 3-CH3 | 5-CH3 | CH3 | 油状物 |
XXXII-10 | CH3 | CH3 | 2-Cl | 4-Cl | CH3 | 油状物 |
XXXII-11 | CH3 | CH3 | 2-Cl | 3-Cl | CH3 | 油状物 |
Claims (17)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19808261A DE19808261A1 (de) | 1998-02-27 | 1998-02-27 | Arylphenylsubstituierte cyclische Ketoenole |
DE19808261.4 | 1998-02-27 |
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CN1298390A CN1298390A (zh) | 2001-06-06 |
CN1280271C true CN1280271C (zh) | 2006-10-18 |
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US (6) | US6417370B1 (zh) |
EP (1) | EP1056717B1 (zh) |
JP (2) | JP4537576B2 (zh) |
KR (1) | KR100577641B1 (zh) |
CN (1) | CN1280271C (zh) |
AR (1) | AR015527A1 (zh) |
AT (1) | ATE299864T1 (zh) |
AU (1) | AU749786B2 (zh) |
BR (1) | BR9909243B1 (zh) |
CA (1) | CA2322158C (zh) |
CO (1) | CO5080737A1 (zh) |
DE (2) | DE19808261A1 (zh) |
ES (1) | ES2244174T3 (zh) |
TW (1) | TWI244480B (zh) |
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- 1999-02-17 JP JP2000533407A patent/JP4537576B2/ja not_active Expired - Fee Related
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- 1999-02-17 BR BRPI9909243-3A patent/BR9909243B1/pt not_active IP Right Cessation
- 1999-02-17 CN CNB998055204A patent/CN1280271C/zh not_active Expired - Fee Related
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2002
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