CN1298390A - 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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- CN1298390A CN1298390A CN99805520A CN99805520A CN1298390A CN 1298390 A CN1298390 A CN 1298390A CN 99805520 A CN99805520 A CN 99805520A CN 99805520 A CN99805520 A CN 99805520A CN 1298390 A CN1298390 A CN 1298390A
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- Prior art keywords
- alkyl
- optionally
- alkoxy
- substituted
- represent
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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 452
- 239000001257 hydrogen Substances 0.000 claims abstract description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 87
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 69
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 56
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 50
- 150000002367 halogens Chemical group 0.000 claims abstract description 46
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000004009 herbicide Substances 0.000 claims abstract description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004660 phenylalkylthio group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 285
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 268
- 238000000034 method Methods 0.000 claims description 194
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 101
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 91
- 238000006243 chemical reaction Methods 0.000 claims description 91
- 239000005864 Sulphur Substances 0.000 claims description 86
- 229910052760 oxygen Inorganic materials 0.000 claims description 84
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 82
- 239000003085 diluting agent Substances 0.000 claims description 82
- 239000001301 oxygen Substances 0.000 claims description 82
- 239000002253 acid Substances 0.000 claims description 75
- 239000000460 chlorine Chemical group 0.000 claims description 71
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 53
- 239000002585 base Substances 0.000 claims description 53
- 229910052801 chlorine Inorganic materials 0.000 claims description 53
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 44
- 239000011737 fluorine Substances 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 44
- 239000003513 alkali Substances 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 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
- 150000001721 carbon Chemical group 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
- 239000011230 binding agent Substances 0.000 claims description 33
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 25
- 125000001544 thienyl group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- 125000000335 thiazolyl group Chemical group 0.000 claims description 17
- 238000006467 substitution reaction Methods 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 14
- 125000004183 alkoxy alkyl 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
- 241000238631 Hexapoda Species 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000002917 insecticide Substances 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 238000009833 condensation Methods 0.000 claims description 11
- 230000005494 condensation Effects 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 9
- 239000011574 phosphorus Substances 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 150000001266 acyl halides Chemical class 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 8
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 229910021645 metal ion Inorganic materials 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 6
- 238000006073 displacement reaction Methods 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 230000036541 health Effects 0.000 claims description 5
- 238000003402 intramolecular cyclocondensation reaction Methods 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
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000002084 enol ethers Chemical class 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 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
- 150000003556 thioamides Chemical class 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical class SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006884 silylation reaction Methods 0.000 claims description 3
- WAJHVCLRPHFEFS-UHFFFAOYSA-N (1-butan-2-yloxy-2-methylpropan-2-yl) hypofluorite Chemical compound C(C)(CC)OCC(C)(C)OF WAJHVCLRPHFEFS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 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
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- NBYQXBYMEUOBON-UHFFFAOYSA-N carbamothioyl chloride Chemical compound NC(Cl)=S NBYQXBYMEUOBON-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000005171 cycloalkylsulfanyl group Chemical group 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
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 claims description 2
- 229910000765 intermetallic Inorganic materials 0.000 claims description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 13
- 238000009313 farming Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 101000780199 Bos taurus Acyl-coenzyme A synthetase ACSM1, mitochondrial Proteins 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 382
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- 239000000203 mixture Substances 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 46
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 41
- 239000007858 starting material Substances 0.000 description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 241000196324 Embryophyta Species 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 27
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 235000019441 ethanol Nutrition 0.000 description 22
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
- 239000000370 acceptor Substances 0.000 description 17
- 238000007796 conventional method Methods 0.000 description 17
- 150000002170 ethers Chemical class 0.000 description 17
- 230000008569 process Effects 0.000 description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 description 17
- 235000017550 sodium carbonate Nutrition 0.000 description 17
- 239000000126 substance Substances 0.000 description 17
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 230000008859 change Effects 0.000 description 16
- 239000003995 emulsifying agent Substances 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 235000011181 potassium carbonates Nutrition 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 244000025254 Cannabis sativa Species 0.000 description 12
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 230000000895 acaricidal effect Effects 0.000 description 12
- 229910052783 alkali metal Inorganic materials 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 239000004519 grease Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 11
- 229910001413 alkali metal ion Inorganic materials 0.000 description 11
- 150000001340 alkali metals Chemical class 0.000 description 11
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 11
- 150000003851 azoles Chemical class 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000003960 organic solvent Substances 0.000 description 11
- 239000002798 polar solvent Substances 0.000 description 11
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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
- 229960003424 phenylacetic acid Drugs 0.000 description 10
- 239000003279 phenylacetic acid Substances 0.000 description 10
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 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
- 240000007594 Oryza sativa Species 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
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- 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
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 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
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
- 241000701366 unidentified nuclear polyhedrosis viruses Species 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 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
- 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
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
- 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
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- 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
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- 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
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- 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
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- 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
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- 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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- C07C69/22—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen having three or more carbon atoms in the acid moiety
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- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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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 | 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 | |
l-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-l-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 | |
1-1-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 | 8 | |
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-l-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 | |
11.9 | 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 | B | |
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 (27)
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DE19808261A DE19808261A1 (de) | 1998-02-27 | 1998-02-27 | Arylphenylsubstituierte cyclische Ketoenole |
DE19808261.4 | 1998-02-27 |
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DE (2) | DE19808261A1 (zh) |
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DE19538218A1 (de) | 1995-10-13 | 1997-04-17 | Bayer Ag | Cyclopentan-1,3-dion-Derivate |
DE19540080A1 (de) | 1995-10-27 | 1997-04-30 | Bayer Ag | 3-Aryl-5-halogen-pyron-Derivate |
DE19544457A1 (de) | 1995-11-29 | 1997-06-05 | Bayer Ag | Oxymethoxy-3-aryl-pyron-Derivate |
DE19649665A1 (de) | 1996-04-02 | 1997-10-09 | Bayer Ag | Neue substituierte Phenylketoenole |
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DE19935963A1 (de) * | 1999-07-30 | 2001-02-01 | Bayer Ag | Biphenylsubstituierte cyclische Ketoenole |
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1998
- 1998-02-27 DE DE19808261A patent/DE19808261A1/de not_active Withdrawn
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1999
- 1999-02-17 CA CA002322158A patent/CA2322158C/en not_active Expired - Fee Related
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- 1999-02-17 US US09/623,016 patent/US6417370B1/en not_active Expired - Lifetime
- 1999-02-17 AT AT99904881T patent/ATE299864T1/de not_active IP Right Cessation
- 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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- 1999-02-17 KR KR1020007008727A patent/KR100577641B1/ko not_active IP Right Cessation
- 1999-02-17 AU AU25231/99A patent/AU749786B2/en not_active Ceased
- 1999-02-26 CO CO99012198A patent/CO5080737A1/es unknown
- 1999-02-26 ZA ZA9901568A patent/ZA991568B/xx unknown
- 1999-02-26 AR ARP990100827A patent/AR015527A1/es active IP Right Grant
- 1999-02-26 TW TW088102895A patent/TWI244480B/zh active
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2002
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2004
- 2004-02-12 US US10/777,528 patent/US7105471B2/en not_active Expired - Fee Related
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN1832938B (zh) * | 2003-06-12 | 2011-05-25 | 拜尔农作物科学股份公司 | N-杂环基苯基-取代的环酮烯醇类化合物 |
CN114984963A (zh) * | 2022-06-30 | 2022-09-02 | 东营科尔特新材料有限公司 | 镍基催化剂及其制备方法和在顺丁烯二酸酐加氢制备丁二酸酐中的应用 |
CN114984963B (zh) * | 2022-06-30 | 2023-12-19 | 东营科尔特新材料有限公司 | 镍基催化剂及其制备方法和在顺丁烯二酸酐加氢制备丁二酸酐中的应用 |
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