DE19528305A1 - Substituierte Phenyluracile - Google Patents

Substituierte Phenyluracile

Info

Publication number: DE19528305A1
Authority: DE; Germany
Prior art keywords: cyano; alkyl; alkoxy; phenyl; chlorine
Prior art date: 1995-08-02
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE1995128305

Other languages

German (de)

English (en)

Inventor

Karl-Heinz Linker

Kurt Prof Dr Findeisen

Roland Dr Andree

Mark Wilhelm Dr Drewes

Markus Dr Dollinger

Hans-Joachim Dr Santel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date 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 date listed.)

1995-08-02

Filing date

1995-08-02

Publication date

1997-02-06

1995-08-02 Application filed by Bayer AG filed Critical Bayer AG

1995-08-02 Priority to DE1995128305 priority Critical patent/DE19528305A1/de

1996-07-22 Priority to PCT/EP1996/003222 priority patent/WO1997005117A1/fr

1996-07-22 Priority to AU66585/96A priority patent/AU6658596A/en

1997-02-06 Publication of DE19528305A1 publication Critical patent/DE19528305A1/de

Status Withdrawn legal-status Critical Current

Links

UIKIQOAXFYAWPW-UHFFFAOYSA-N 5-phenyl-1h-pyrimidine-2,4-dione Chemical class O=C1NC(=O)NC=C1C1=CC=CC=C1 UIKIQOAXFYAWPW-UHFFFAOYSA-N 0.000 title claims 2
-1 cyano, carbamoyl Chemical group 0.000 claims abstract description 316
239000001257 hydrogen Substances 0.000 claims abstract description 46
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
125000003545 alkoxy group Chemical group 0.000 claims abstract description 43
150000001875 compounds Chemical class 0.000 claims abstract description 40
229910052736 halogen Inorganic materials 0.000 claims abstract description 39
150000002367 halogens Chemical class 0.000 claims abstract description 39
125000000217 alkyl group Chemical group 0.000 claims abstract description 35
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 25
125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 24
125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 19
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 19
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
125000005108 alkenylthio group Chemical group 0.000 claims abstract description 10
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 10
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 9
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 9
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
239000004009 herbicide Substances 0.000 claims abstract description 7
FPXYZAPIQZZTTA-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-2,4-dioxopyrimidine-5-carbonitrile Chemical compound C1=C(Cl)C(F)=CC=C1N1C(=O)NC(=O)C(C#N)=C1 FPXYZAPIQZZTTA-UHFFFAOYSA-N 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract 24
239000000460 chlorine Chemical group 0.000 claims description 64
229910052801 chlorine Inorganic materials 0.000 claims description 64
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 62
229910052731 fluorine Inorganic materials 0.000 claims description 37
239000011737 fluorine Substances 0.000 claims description 36
229910052794 bromium Chemical group 0.000 claims description 34
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 33
238000000034 method Methods 0.000 claims description 23
125000000304 alkynyl group Chemical group 0.000 claims description 21
125000001153 fluoro group Chemical group F* 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 15
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
125000005133 alkynyloxy group Chemical group 0.000 claims description 12
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
239000001301 oxygen Substances 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000011593 sulfur Substances 0.000 claims description 12
CLKZWXHKFXZIMA-UHFFFAOYSA-N pyrinuron Chemical group C1=CC([N+](=O)[O-])=CC=C1NC(=O)NCC1=CC=CN=C1 CLKZWXHKFXZIMA-UHFFFAOYSA-N 0.000 claims description 9
125000005109 alkynylthio group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
WQSLEOSEZJMCQX-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2,4-dioxopyrimidine-5-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1N1C(=O)NC(=O)C(C#N)=C1 WQSLEOSEZJMCQX-UHFFFAOYSA-N 0.000 claims description 7
XDASRKBAKXZGNH-UHFFFAOYSA-N 1-(4-chloro-2-fluoro-5-prop-2-ynoxyphenyl)-3-methylpyridine-2,4-dione Chemical compound ClC1=CC(=C(C=C1OCC#C)N1C(C(C(C=C1)=O)C)=O)F XDASRKBAKXZGNH-UHFFFAOYSA-N 0.000 claims description 7
GHZVKFGWUXFHSM-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-2,4-dioxopyrimidine-5-carbonitrile Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(N2C(NC(=O)C(C#N)=C2)=O)=C1 GHZVKFGWUXFHSM-UHFFFAOYSA-N 0.000 claims description 7
239000003085 diluting agent Substances 0.000 claims description 7
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
230000000694 effects Effects 0.000 claims description 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
125000001786 isothiazolyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 6
125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
125000003226 pyrazolyl group Chemical group 0.000 claims description 6
125000000168 pyrrolyl group Chemical group 0.000 claims description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
125000006323 alkenyl amino group Chemical group 0.000 claims description 4
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 4
125000006319 alkynyl amino group Chemical group 0.000 claims description 4
125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
125000005879 dioxolanyl group Chemical group 0.000 claims description 4
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
125000000466 oxiranyl group Chemical group 0.000 claims description 4
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
HMZJBKATTSGEKP-UHFFFAOYSA-N FC(=O)OC#N Chemical compound FC(=O)OC#N HMZJBKATTSGEKP-UHFFFAOYSA-N 0.000 claims description 3
239000004606 Fillers/Extenders Substances 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 3
125000003566 oxetanyl group Chemical group 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
230000002363 herbicidal effect Effects 0.000 claims description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
125000006513 pyridinyl methyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004306 triazinyl group Chemical group 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 8
WFBNNMQTNRAESJ-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)-2,4-dioxopyrimidine-5-carbonitrile Chemical compound FC1=CC(Cl)=CC=C1N1C(=O)NC(=O)C(C#N)=C1 WFBNNMQTNRAESJ-UHFFFAOYSA-N 0.000 abstract description 5
125000006193 alkinyl group Chemical group 0.000 abstract 3
229910052799 carbon Inorganic materials 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
241000196324 Embryophyta Species 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
239000007858 starting material Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
125000004356 hydroxy functional group Chemical group O* 0.000 description 8
239000002904 solvent Substances 0.000 description 8
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 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000003995 emulsifying agent Substances 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000002689 soil Substances 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
239000000047 product Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000126 substance Substances 0.000 description 4
241000219144 Abutilon Species 0.000 description 3
241000219318 Amaranthus Species 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241000209510 Liliopsida Species 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
235000005775 Setaria Nutrition 0.000 description 3
241000232088 Setaria <nematode> Species 0.000 description 3
241000220261 Sinapis Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
241001233957 eudicotyledons Species 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
239000011435 rock Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
241000743985 Alopecurus Species 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000234653 Cyperus Species 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
235000021506 Ipomoea Nutrition 0.000 description 2
241000207783 Ipomoea Species 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000209117 Panicum Species 0.000 description 2
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
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RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
150000002897 organic nitrogen compounds Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
229940067631 phospholipid Drugs 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000012545 processing Methods 0.000 description 1
MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
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
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-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
GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
- C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

DE1995128305 1995-08-02 1995-08-02 Substituierte Phenyluracile Withdrawn DE19528305A1 (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
DE1995128305 DE19528305A1 (de)	1995-08-02	1995-08-02	Substituierte Phenyluracile
PCT/EP1996/003222 WO1997005117A1 (fr)	1995-08-02	1996-07-22	Derives substitues de 1-phenyluracile, leur preparation et leur utilisation comme herbicides
AU66585/96A AU6658596A (en)	1995-08-02	1996-07-22	Substituted 1-phenyluracil derivatives, their preparation and their use as herbicides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE1995128305 DE19528305A1 (de)	1995-08-02	1995-08-02	Substituierte Phenyluracile

Publications (1)

Publication Number	Publication Date
DE19528305A1 true DE19528305A1 (de)	1997-02-06

Family

ID=7768458

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE1995128305 Withdrawn DE19528305A1 (de)	1995-08-02	1995-08-02	Substituierte Phenyluracile

Country Status (3)

Country	Link
AU (1)	AU6658596A (fr)
DE (1)	DE19528305A1 (fr)
WO (1)	WO1997005117A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997042176A1 (fr) *	1996-05-02	1997-11-13	Bayer Aktiengesellschaft	Phenyluraciles substitues et leur utilisation comme herbicides
WO1998002422A1 (fr) *	1996-07-11	1998-01-22	Bayer Aktiengesellschaft	Composes aromatiques substitues de carbonyle et leurs derives
WO1998047904A1 (fr) *	1997-04-22	1998-10-29	E.I. Du Pont De Nemours And Company	Sulfonamides herbicides
WO2014202510A1 (fr)	2013-06-20	2014-12-24	Bayer Cropscience Ag	Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2014202505A1 (fr)	2013-06-20	2014-12-24	Bayer Cropscience Ag	Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2015004028A1 (fr)	2013-07-08	2015-01-15	Bayer Cropscience Ag	Dérivés de sulfures et sulfoxydes d'aryles hexacycliques à liaison c‑n utilisés comme pesticides

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19722031A1 (de) *	1997-05-27	1998-12-03	Bayer Ag	Substituierte Iminoalkoxy-phenyluracile
TW200510305A (en)	2003-07-25	2005-03-16	Wyeth Corp	Process for the preparation of CPLA2 inhibitors
PA8796201A1 (es)	2007-09-17	2009-04-23	Abbott Lab	Agentes anti-infecciosos y su uso
PL2639226T3 (pl)	2007-09-17	2017-02-28	Abbvie Bahamas Ltd.	Pirymidyny o działaniu przeciw zakaźnym oraz ich zastosowania
CN101918369B (zh)	2007-09-17	2016-02-24	艾伯维巴哈马有限公司	治疗丙型肝炎的尿嘧啶或胸腺嘧啶衍生物
US9216952B2 (en)	2010-03-23	2015-12-22	Abbvie Inc.	Process for preparing antiviral compound
CA2805748A1 (fr)	2010-07-16	2012-01-19	Shashank Shekhar	Procede de preparation de composes antiviraux
US9255074B2 (en)	2010-07-16	2016-02-09	Abbvie Inc.	Process for preparing antiviral compounds
SG187103A1 (en)	2010-07-16	2013-02-28	Abbvie Inc	Phosphine ligands for catalytic reactions
US8975443B2 (en)	2010-07-16	2015-03-10	Abbvie Inc.	Phosphine ligands for catalytic reactions

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4266056A (en) *	1978-04-07	1981-05-05	Zoecon Corporation	Phenyl uracils
GB2043628B (en) *	1978-12-14	1983-05-25	Zoecon Corp	1-phenyl-3-polyhaloalkyl thio or polyhalovinyl thio uracils useful as biological agents and synthesis thereof
US5298502A (en) *	1988-12-12	1994-03-29	Fmc Corporation	Method and composition for photodynamic treatment and detection of tumors
US5153316A (en) *	1991-06-04	1992-10-06	Crouse Gary D	Intermediates for herbicidal phenylimidazolones

1995
- 1995-08-02 DE DE1995128305 patent/DE19528305A1/de not_active Withdrawn
1996
- 1996-07-22 AU AU66585/96A patent/AU6658596A/en not_active Abandoned
- 1996-07-22 WO PCT/EP1996/003222 patent/WO1997005117A1/fr not_active Ceased

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1997042176A1 (fr) *	1996-05-02	1997-11-13	Bayer Aktiengesellschaft	Phenyluraciles substitues et leur utilisation comme herbicides
WO1998002422A1 (fr) *	1996-07-11	1998-01-22	Bayer Aktiengesellschaft	Composes aromatiques substitues de carbonyle et leurs derives
WO1998047904A1 (fr) *	1997-04-22	1998-10-29	E.I. Du Pont De Nemours And Company	Sulfonamides herbicides
WO2014202510A1 (fr)	2013-06-20	2014-12-24	Bayer Cropscience Ag	Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2014202505A1 (fr)	2013-06-20	2014-12-24	Bayer Cropscience Ag	Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2015004028A1 (fr)	2013-07-08	2015-01-15	Bayer Cropscience Ag	Dérivés de sulfures et sulfoxydes d'aryles hexacycliques à liaison c‑n utilisés comme pesticides
US9783509B2 (en)	2013-07-08	2017-10-10	Bayer Cropscience Aktiengesellschaft	Six-membered C-N-linked aryl sulfide derivatives and aryl sulfoxide derivatives as pest conrol agents

Also Published As

Publication number	Publication date
WO1997005117A1 (fr)	1997-02-13
AU6658596A (en)	1997-02-26

Legal Events

Date	Code	Title	Description
1998-08-13	8139	Disposal/non-payment of the annual fee

Publication	Publication Date	Title
EP0832072B1 (fr)	2003-09-24	Phenylpyridazinones
EP0648749B1 (fr)	1997-12-10	N-cyanoaryle hétérocycles azotés
EP0759908B1 (fr)	2003-04-02	Diazacyclohexandi(thi)ones substituees
EP0757680B1 (fr)	2003-07-02	Heterocycles n-cyanoaryle-azote
EP1120411B1 (fr)	2004-09-22	Dérivés de 4-aryl-1,2,4-triazolidinedione et leur utilisation comme herbicides
DE19528305A1 (de)	1997-02-06	Substituierte Phenyluracile
EP0842155B1 (fr)	2003-04-09	Amino-uraciles substitues
DE19606594A1 (de)	1997-08-28	Substituierte 2-Aryl-1,2,4-triazin-3,5-di(thi)one
EP0835247A1 (fr)	1998-04-15	Carbonylaminophenyluraciles substitues
DE4431218A1 (de)	1996-03-07	Substituierte Pyrimidin(thi)one
DE4424787A1 (de)	1996-01-18	Substituierte Aryliminoheterocyclen
DE19632005A1 (de)	1998-02-12	Substituierte p-Trifluormethylphenyluracile
DE4440914A1 (de)	1996-05-23	Substituierte Diazacyclohexandi(thi)one
DE19532347A1 (de)	1997-03-06	4-Thiocarbamoyl-1-(3-pyrazolyl)-pyrazole
DE19617532A1 (de)	1997-11-06	Substituierte Phenyluracile
EP0906291B1 (fr)	2005-03-09	Phenyluraciles substitues
EP0843667B1 (fr)	2001-10-17	Phenyluraciles substitues
DE19530451A1 (de)	1997-02-20	Substituierte Chinazolin(thi)one
DE4437295A1 (de)	1995-10-26	N-Cyanoaryl-Stickstoffheterocyclen
DE19517732A1 (de)	1996-11-21	Aminouracilderivate
DE19702435A1 (de)	1998-07-30	Arylalkylverbindungen