JP2013500956A5

JP2013500956A5 -

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Publication number: JP2013500956A5
Authority: JP; Japan
Prior art keywords: alkyl; formula; compound; halogen; alkoxy
Prior art date: 2010-07-29
Legal status : Granted

Application number

JP2012522243A

Other languages

English (en)

Japanese (ja)

Other versions

JP5795581B2 (ja

JP2013500956A (ja

Filing date

2010-07-29

Publication date

2013-09-12

2009-07-31 Priority claimed from GB0913436A external-priority patent/GB0913436D0/en

2010-07-27 Priority claimed from GBGB1012582.1A external-priority patent/GB201012582D0/en

2010-07-29 Application filed filed Critical

2010-07-29 Priority claimed from PCT/GB2010/001449 external-priority patent/WO2011012862A1/en

2013-01-10 Publication of JP2013500956A publication Critical patent/JP2013500956A/ja

2013-09-12 Publication of JP2013500956A5 publication Critical patent/JP2013500956A5/ja

2015-10-14 Application granted granted Critical

2015-10-14 Publication of JP5795581B2 publication Critical patent/JP5795581B2/ja

Status Expired - Fee Related legal-status Critical Current

2030-07-29 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 851
125000000217 alkyl group Chemical group 0.000 claims description 298
229910052736 halogen Inorganic materials 0.000 claims description 228
150000002367 halogens Chemical class 0.000 claims description 223
-1 C1-C6Alkoxy Chemical group 0.000 claims description 212
229910052739 hydrogen Inorganic materials 0.000 claims description 159
239000001257 hydrogen Substances 0.000 claims description 158
125000004093 cyano group Chemical group *C#N 0.000 claims description 125
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 103
125000001072 heteroaryl group Chemical group 0.000 claims description 99
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 85
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
239000000203 mixture Substances 0.000 claims description 80
125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 67
238000000034 method Methods 0.000 claims description 67
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
150000002431 hydrogen Chemical class 0.000 claims description 55
239000004009 herbicide Substances 0.000 claims description 54
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 47
125000003118 aryl group Chemical group 0.000 claims description 47
125000004438 haloalkoxy group Chemical group 0.000 claims description 46
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 42
230000002363 herbicidal effect Effects 0.000 claims description 41
241000196324 Embryophyta Species 0.000 claims description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
125000001188 haloalkyl group Chemical group 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 22
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 15
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
229910052799 carbon Inorganic materials 0.000 claims description 14
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
240000008042 Zea mays Species 0.000 claims description 12
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 12
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 12
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
235000005822 corn Nutrition 0.000 claims description 12
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
244000038559 crop plants Species 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000004970 halomethyl group Chemical group 0.000 claims description 11
125000005241 heteroarylamino group Chemical group 0.000 claims description 11
125000002950 monocyclic group Chemical group 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
238000002156 mixing Methods 0.000 claims description 10
125000002971 oxazolyl group Chemical group 0.000 claims description 10
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 9
229920002554 vinyl polymer Polymers 0.000 claims description 9
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000004076 pyridyl group Chemical group 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 7
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 7
125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
150000001342 alkaline earth metals Chemical class 0.000 claims description 7
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
235000013339 cereals Nutrition 0.000 claims description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 7
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 6
125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 6
240000007594 Oryza sativa Species 0.000 claims description 6
235000007164 Oryza sativa Nutrition 0.000 claims description 6
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000002098 pyridazinyl group Chemical group 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
235000009566 rice Nutrition 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 5
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
235000010469 Glycine max Nutrition 0.000 claims description 5
229930194542 Keto Natural products 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 claims description 5
125000004969 haloethyl group Chemical group 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 5
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 4
125000005240 diheteroarylamino group Chemical group 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
244000025254 Cannabis sativa Species 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 2
125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 2
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 3
125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 2
244000068988 Glycine max Species 0.000 claims 1
125000005138 alkoxysulfonyl group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 claims 1
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims 1
125000005291 haloalkenyloxy group Chemical group 0.000 claims 1
125000000232 haloalkynyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 124
238000006243 chemical reaction Methods 0.000 description 108
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 88
239000002904 solvent Substances 0.000 description 79
238000002360 preparation method Methods 0.000 description 68
239000000243 solution Substances 0.000 description 67
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
239000002585 base Substances 0.000 description 50
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
235000019439 ethyl acetate Nutrition 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 40
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
239000003921 oil Substances 0.000 description 36
235000019198 oils Nutrition 0.000 description 35
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 25
238000009472 formulation Methods 0.000 description 24
239000000460 chlorine Substances 0.000 description 23
229910052801 chlorine Inorganic materials 0.000 description 23
230000002829 reductive effect Effects 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000004480 active ingredient Substances 0.000 description 21
125000000623 heterocyclic group Chemical group 0.000 description 21
239000000377 silicon dioxide Substances 0.000 description 21
239000007787 solid Substances 0.000 description 21
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000000654 additive Substances 0.000 description 18
238000003818 flash chromatography Methods 0.000 description 18
239000003795 chemical substances by application Substances 0.000 description 17
229910052763 palladium Inorganic materials 0.000 description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 16
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
229910052943 magnesium sulfate Inorganic materials 0.000 description 16
235000019341 magnesium sulphate Nutrition 0.000 description 16
230000008569 process Effects 0.000 description 16
239000011541 reaction mixture Substances 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
238000003756 stirring Methods 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
244000075850 Avena orientalis Species 0.000 description 15
125000003342 alkenyl group Chemical group 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
238000013459 approach Methods 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
239000004094 surface-active agent Substances 0.000 description 14
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 13
125000000304 alkynyl group Chemical group 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
0 *CC(*)C(*(C(*)(C(*)(*)C(C1*)=O)C1=O)=C)S Chemical compound *CC(*)C(*(C(*)(C(*)(*)C(C1*)=O)C1=O)=C)S 0.000 description 12
235000007319 Avena orientalis Nutrition 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000002671 adjuvant Substances 0.000 description 12
235000019270 ammonium chloride Nutrition 0.000 description 12
239000012299 nitrogen atmosphere Substances 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
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 12
239000003643 water by type Substances 0.000 description 12
150000008052 alkyl sulfonates Chemical class 0.000 description 11
239000003446 ligand Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
239000012071 phase Substances 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
241000209140 Triticum Species 0.000 description 9
235000021307 Triticum Nutrition 0.000 description 9
239000002253 acid Substances 0.000 description 9
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 9
230000029936 alkylation Effects 0.000 description 9
238000005804 alkylation reaction Methods 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
125000004122 cyclic group Chemical group 0.000 description 9
239000010410 layer Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000007921 spray Substances 0.000 description 9
239000013058 crude material Substances 0.000 description 8
125000004663 dialkyl amino group Chemical group 0.000 description 8
125000003709 fluoroalkyl group Chemical group 0.000 description 8
238000010438 heat treatment Methods 0.000 description 8
239000007788 liquid Substances 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
238000002953 preparative HPLC Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
238000012360 testing method Methods 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
QJHQBOBUAOFVLH-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3-thiazole-5-carbaldehyde Chemical compound C1=CC(Cl)=CC=C1C1=NC=C(C=O)S1 QJHQBOBUAOFVLH-UHFFFAOYSA-N 0.000 description 7
125000004414 alkyl thio group Chemical group 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
238000006880 cross-coupling reaction Methods 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
235000011181 potassium carbonates Nutrition 0.000 description 7
125000003107 substituted aryl group Chemical group 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
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YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
229940087291 tridecyl alcohol Drugs 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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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RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
MDTPTXSNPBAUHX-UHFFFAOYSA-M trimethylsulfanium;hydroxide Chemical compound [OH-].C[S+](C)C MDTPTXSNPBAUHX-UHFFFAOYSA-M 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
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JP2012522243A 2009-07-31 2010-07-29 除草活性を有するヘテロアリール置換環状ジオンまたはその誘導体 Expired - Fee Related JP5795581B2 (ja)