JPH0479348B2 - - Google Patents

Info

Publication number

JPH0479348B2

JPH0479348B2 JP12354684A JP12354684A JPH0479348B2 JP H0479348 B2 JPH0479348 B2 JP H0479348B2 JP 12354684 A JP12354684 A JP 12354684A JP 12354684 A JP12354684 A JP 12354684A JP H0479348 B2 JPH0479348 B2 JP H0479348B2

Authority

JP

Japan

Prior art keywords

carbon atoms

hydrogen

oxo

dihydrofuran

phenyl

Prior art date

1984-06-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired

Links

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• 150000001875 compounds Chemical class 0.000 claims description 141
• 125000004432 carbon atom Chemical group C* 0.000 claims description 84
• 229910052739 hydrogen Inorganic materials 0.000 claims description 72
• 239000001257 hydrogen Substances 0.000 claims description 72
• -1 1-indenyl Chemical group 0.000 claims description 64
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• 238000000034 method Methods 0.000 claims description 55
• 239000000203 mixture Substances 0.000 claims description 53
• 125000005843 halogen group Chemical group 0.000 claims description 46
• 150000002431 hydrogen Chemical class 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 238000006243 chemical reaction Methods 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 239000003960 organic solvent Substances 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 125000001188 haloalkyl group Chemical group 0.000 claims description 20
• 230000002363 herbicidal effect Effects 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
• 239000011737 fluorine Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical group 0.000 claims description 11
• 229910052740 iodine Inorganic materials 0.000 claims description 11
• 239000011630 iodine Substances 0.000 claims description 11
• 239000007788 liquid Substances 0.000 claims description 11
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000003107 substituted aryl group Chemical group 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 7
• 229910052757 nitrogen Inorganic materials 0.000 claims description 7
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 230000001629 suppression Effects 0.000 claims description 2
• 125000003710 aryl alkyl group Chemical group 0.000 claims 4
• 230000006378 damage Effects 0.000 claims 1
• 125000005059 halophenyl group Chemical group 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
• 239000002585 base Substances 0.000 description 22
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• 241000196324 Embryophyta Species 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 239000007858 starting material Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 238000012360 testing method Methods 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 239000000376 reactant Substances 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
• 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 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• 229960000583 acetic acid Drugs 0.000 description 5
• 150000004820 halides Chemical class 0.000 description 5
• 238000011065 in-situ storage Methods 0.000 description 5
• 239000003208 petroleum Substances 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• 239000011734 sodium Substances 0.000 description 5
• 239000012312 sodium hydride Substances 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 239000000443 aerosol Substances 0.000 description 4
• 150000001340 alkali metals Chemical class 0.000 description 4
• 239000002168 alkylating agent Substances 0.000 description 4
• 229940100198 alkylating agent Drugs 0.000 description 4
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• JOIYKSLWXLFGGR-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]acetonitrile Chemical compound FC(F)(F)C1=CC=CC(CC#N)=C1 JOIYKSLWXLFGGR-UHFFFAOYSA-N 0.000 description 3
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 230000002152 alkylating effect Effects 0.000 description 3
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
• 125000003277 amino group Chemical group 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• 238000004587 chromatography analysis Methods 0.000 description 3
• 150000008050 dialkyl sulfates Chemical class 0.000 description 3
• VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 230000035784 germination Effects 0.000 description 3
• 230000000269 nucleophilic effect Effects 0.000 description 3
• 230000003287 optical effect Effects 0.000 description 3
• 230000000885 phytotoxic effect Effects 0.000 description 3
• 230000008635 plant growth Effects 0.000 description 3
• 229910000105 potassium hydride Inorganic materials 0.000 description 3
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 3
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
• 239000011541 reaction mixture Substances 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 239000002689 soil Substances 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
• MPJJVXQPHWVWSG-UHFFFAOYSA-N 2-(2-chloro-3-methylphenyl)-3-oxo-4-phenylbutanenitrile Chemical compound CC1=CC=CC(C(C#N)C(=O)CC=2C=CC=CC=2)=C1Cl MPJJVXQPHWVWSG-UHFFFAOYSA-N 0.000 description 2
• ICPWFHKNYYRBSZ-UHFFFAOYSA-M 2-methoxypropanoate Chemical compound COC(C)C([O-])=O ICPWFHKNYYRBSZ-UHFFFAOYSA-M 0.000 description 2
• RANMIORLMCIAPH-UHFFFAOYSA-N 3-oxo-4-phenyl-2-[3-(trifluoromethyl)phenyl]butanenitrile Chemical compound FC(F)(F)C1=CC=CC(C(C#N)C(=O)CC=2C=CC=CC=2)=C1 RANMIORLMCIAPH-UHFFFAOYSA-N 0.000 description 2
• GYPDPPGCNPUJMG-UHFFFAOYSA-N 4-(2-chloro-3-methylphenyl)-5-(methylamino)-2-phenylfuran-3-one Chemical compound O1C(NC)=C(C=2C(=C(C)C=CC=2)Cl)C(=O)C1C1=CC=CC=C1 GYPDPPGCNPUJMG-UHFFFAOYSA-N 0.000 description 2
• YSIFROBNNGAQDB-UHFFFAOYSA-N 4-methoxy-5-methyl-3-oxo-2-[3-(trifluoromethyl)phenyl]hexanenitrile Chemical compound COC(C(C)C)C(=O)C(C#N)C1=CC=CC(C(F)(F)F)=C1 YSIFROBNNGAQDB-UHFFFAOYSA-N 0.000 description 2
• CEEMZIOOCCHIAB-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethylsulfanyl)phenyl]furan-3-one Chemical compound O1C(NC)=C(C=2C=C(SC(F)(F)F)C=CC=2)C(=O)C1C1=CC=CC=C1 CEEMZIOOCCHIAB-UHFFFAOYSA-N 0.000 description 2
• RYFMLBQPALMEGU-UHFFFAOYSA-N 5-amino-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O1C(N)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 RYFMLBQPALMEGU-UHFFFAOYSA-N 0.000 description 2
• BUVFLFMEXOZCNM-UHFFFAOYSA-N 5-amino-4-(2-chloro-3-methylphenyl)-2-phenylfuran-3-one Chemical compound CC1=CC=CC(C=2C(C(OC=2N)C=2C=CC=CC=2)=O)=C1Cl BUVFLFMEXOZCNM-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 150000001335 aliphatic alkanes Chemical class 0.000 description 2
• 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
• 150000008046 alkali metal hydrides Chemical class 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• 150000001768 cations Chemical class 0.000 description 2
• 239000003153 chemical reaction reagent Substances 0.000 description 2
• 239000012141 concentrate Substances 0.000 description 2
• 238000010790 dilution Methods 0.000 description 2
• 239000012895 dilution Substances 0.000 description 2
• 235000013312 flour Nutrition 0.000 description 2
• 239000000417 fungicide Substances 0.000 description 2
• 230000012010 growth Effects 0.000 description 2
• 239000004009 herbicide Substances 0.000 description 2
• 125000000623 heterocyclic group Chemical group 0.000 description 2
• 239000002917 insecticide Substances 0.000 description 2
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
• 229910052744 lithium Inorganic materials 0.000 description 2
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
• 229910003002 lithium salt Inorganic materials 0.000 description 2
• 159000000002 lithium salts Chemical class 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 238000012986 modification Methods 0.000 description 2
• 230000004048 modification Effects 0.000 description 2
• 239000012299 nitrogen atmosphere Substances 0.000 description 2
• 239000002736 nonionic surfactant Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• 238000002360 preparation method Methods 0.000 description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
• 235000019260 propionic acid Nutrition 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
• 239000002516 radical scavenger Substances 0.000 description 2
• 230000035484 reaction time Effects 0.000 description 2
• 239000000741 silica gel Substances 0.000 description 2
• 229910002027 silica gel Inorganic materials 0.000 description 2
• 239000002002 slurry Substances 0.000 description 2
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• 239000004094 surface-active agent Substances 0.000 description 2
• 239000012085 test solution Substances 0.000 description 2
• NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
• JLIDRDJNLAWIKT-UHFFFAOYSA-N 1,2-dimethyl-3h-benzo[e]indole Chemical compound C1=CC=CC2=C(C(=C(C)N3)C)C3=CC=C21 JLIDRDJNLAWIKT-UHFFFAOYSA-N 0.000 description 1
• IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000006017 1-propenyl group Chemical group 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical class C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 1
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
• HMEXDVGUGPYLQG-UHFFFAOYSA-N 2,3-dihydrofuran-5-amine Chemical compound NC1=CCCO1 HMEXDVGUGPYLQG-UHFFFAOYSA-N 0.000 description 1
• PQHLSFKNTRHGOP-UHFFFAOYSA-N 2-(1-chloroethenyl)-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C(Cl)=C)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 PQHLSFKNTRHGOP-UHFFFAOYSA-N 0.000 description 1
• PEHUTKMBCZECOQ-UHFFFAOYSA-N 2-(1h-inden-1-yl)-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(C2C3=CC=CC=C3C=C2)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 PEHUTKMBCZECOQ-UHFFFAOYSA-N 0.000 description 1
• ZOOXKLCYHWARGC-UHFFFAOYSA-N 2-(1h-inden-1-ylmethylidene)-5-(methylamino)-4-[3-(trifluoromethyl)phenyl]furan-3-one Chemical compound O=C1C(=CC2C3=CC=CC=C3C=C2)OC(NC)=C1C1=CC=CC(C(F)(F)F)=C1 ZOOXKLCYHWARGC-UHFFFAOYSA-N 0.000 description 1
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• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
• 239000012044 organic layer Substances 0.000 description 1
• 229910052625 palygorskite Inorganic materials 0.000 description 1
• 229940049953 phenylacetate Drugs 0.000 description 1
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 239000005648 plant growth regulator Substances 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
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• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• XPSQRFGOPLDGPO-UHFFFAOYSA-N sodium;dimethylazanide Chemical compound [Na+].C[N-]C XPSQRFGOPLDGPO-UHFFFAOYSA-N 0.000 description 1
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
• KLPPUPBECAHKEF-UHFFFAOYSA-N thiophen-2-ylsulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CS1 KLPPUPBECAHKEF-UHFFFAOYSA-N 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
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• 238000012546 transfer Methods 0.000 description 1
• 238000011282 treatment Methods 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
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