HUT77013A - Aril-uracilok alkalmazása félig szelektív és nemszelektív gyomirtásra - Google Patents
Aril-uracilok alkalmazása félig szelektív és nemszelektív gyomirtásra Download PDFInfo
- Publication number
- HUT77013A HUT77013A HU9701964A HU9701964A HUT77013A HU T77013 A HUT77013 A HU T77013A HU 9701964 A HU9701964 A HU 9701964A HU 9701964 A HU9701964 A HU 9701964A HU T77013 A HUT77013 A HU T77013A
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- hydrogen
- optionally substituted
- chloro
- alkoxy
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims description 18
- -1 aryl uracil Chemical compound 0.000 claims description 175
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 56
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 239000001301 oxygen Substances 0.000 claims description 32
- 239000011593 sulfur Substances 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 230000002363 herbicidal effect Effects 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
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 11
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 claims description 11
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims description 10
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims description 10
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 10
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 claims description 9
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 claims description 8
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 235000013877 carbamide Nutrition 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 claims description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 6
- 150000003222 pyridines Chemical class 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 229940035893 uracil Drugs 0.000 claims description 6
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 claims description 5
- ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 claims description 5
- 239000005630 Diquat Substances 0.000 claims description 5
- 239000005510 Diuron Substances 0.000 claims description 5
- 239000005562 Glyphosate Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000005583 Metribuzin Substances 0.000 claims description 5
- 239000005590 Oxyfluorfen Substances 0.000 claims description 5
- 239000005627 Triclopyr Substances 0.000 claims description 5
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 claims description 5
- 229940097068 glyphosate Drugs 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 claims description 5
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- VBRQSQVALDRCOF-UHFFFAOYSA-N 2-(4-amino-3,5,6-trichloropyridin-2-yl)oxyacetic acid Chemical compound NC1=C(Cl)C(Cl)=NC(OCC(O)=O)=C1Cl VBRQSQVALDRCOF-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- LQZPNZSICBVXTB-UHFFFAOYSA-N OCP(=O)CCCC(O)=O Chemical compound OCP(=O)CCCC(O)=O LQZPNZSICBVXTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000011664 nicotinic acid Substances 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 1
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 3
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 101000873645 Homo sapiens Secretory carrier-associated membrane protein 3 Proteins 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 102100035895 Secretory carrier-associated membrane protein 3 Human genes 0.000 description 2
- HFBHZUIZMSQSJO-UHFFFAOYSA-N [NH4+].[O-]C(=O)C(N)CCP(=O)CO Chemical compound [NH4+].[O-]C(=O)C(N)CCP(=O)CO HFBHZUIZMSQSJO-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 229950000329 thiouracil Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NACWJEQGDKTEKR-UHFFFAOYSA-M 1,1-dimethyl-4-pyridin-1-ium-4-yl-2h-pyridin-1-ium;dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)(C)CC=C1C1=CC=[NH+]C=C1 NACWJEQGDKTEKR-UHFFFAOYSA-M 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- RAHNAFFWINHVGY-UHFFFAOYSA-N 4-methyl-4-propan-2-yl-2-pyridin-2-yl-1h-imidazol-5-one Chemical compound O=C1C(C(C)C)(C)NC(C=2N=CC=CC=2)=N1 RAHNAFFWINHVGY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4432888A DE4432888A1 (de) | 1994-09-15 | 1994-09-15 | Verwendung von Aryluracilen im semi- und nicht-selektiven Bereich der Unkrautbekämpfung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HUT77013A true HUT77013A (hu) | 1998-03-02 |
Family
ID=6528309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9701964A HUT77013A (hu) | 1994-09-15 | 1995-09-04 | Aril-uracilok alkalmazása félig szelektív és nemszelektív gyomirtásra |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0781093A1 (enExample) |
| JP (1) | JPH10505603A (enExample) |
| KR (1) | KR970705924A (enExample) |
| CN (1) | CN1157552A (enExample) |
| AU (1) | AU3521395A (enExample) |
| BR (1) | BR9508929A (enExample) |
| CA (1) | CA2199846A1 (enExample) |
| DE (1) | DE4432888A1 (enExample) |
| HU (1) | HUT77013A (enExample) |
| MX (1) | MX9701953A (enExample) |
| WO (1) | WO1996008151A1 (enExample) |
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| ZA971253B (en) * | 1996-02-16 | 1998-08-14 | Basf Ag | Substituted aromatic phosphonic acid derivatives |
| DE19605766A1 (de) * | 1996-02-16 | 1997-08-21 | Basf Ag | Substituierte 2-Phenylpyridine |
| UA57070C2 (uk) | 1997-03-14 | 2003-06-16 | Іск Амерікас Інкорпорейтед | Діарилові ефіри, гербіциднa композиція та спосіб боротьби з бур'янами |
| DE19815820A1 (de) * | 1998-04-08 | 1999-10-14 | Hoechst Schering Agrevo Gmbh | Synergistische herbizide Mittel auf Basis von phosphorhaltigen Blattherbiziden, Imidazolinonen und Wuchsstoffherbiziden |
| US6121201A (en) | 1998-09-11 | 2000-09-19 | Ishihara Sangyo Kaisha, Ltd. | Diaryl ethers and processes for their preparation and herbicidal and desiccant compositions containing them |
| JP2000351703A (ja) * | 1999-06-07 | 2000-12-19 | Sumitomo Chem Co Ltd | 除草剤組成物 |
| DE19936438A1 (de) * | 1999-08-03 | 2001-02-08 | Aventis Cropscience Gmbh | Kombinationen von Herbiziden und Safenern |
| DE19958381A1 (de) | 1999-12-03 | 2001-06-07 | Bayer Ag | Herbizide auf Basis von N-Aryl-uracilen |
| IL141034A0 (en) | 2000-02-04 | 2002-02-10 | Sumitomo Chemical Co | Uracil compounds and use thereof |
| NZ517562A (en) | 2000-05-04 | 2004-09-24 | Basf Ag | Uracil substituted phenyl sulfamoyl carboxamides |
| US6617282B2 (en) | 2001-06-26 | 2003-09-09 | Ishihara Sangyo Kaisha, Ltd. | Processes for preparing 3-phenyl-2,4(1H, 3H)-pyrimidinediones |
| US6613718B2 (en) | 2001-10-01 | 2003-09-02 | Ishihara Sangyo Kaisha, Ltd. | Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them |
| US7741485B2 (en) | 2003-04-08 | 2010-06-22 | Basf Aktiengesellschaft | Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds |
| ES2716008T3 (es) | 2012-07-18 | 2019-06-07 | Sunshine Lake Pharma Co Ltd | Derivados heterocíclicos nitrogenados y su aplicación en fármacos |
| US9902712B2 (en) | 2013-12-19 | 2018-02-27 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
| AU2018391580B2 (en) | 2017-12-19 | 2022-08-18 | Syngenta Crop Protection Ag | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
| US11497212B2 (en) | 2017-12-19 | 2022-11-15 | Syngenta Crop Protection Ag | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
| WO2019121547A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| BR112022000595A2 (pt) | 2019-07-22 | 2022-07-19 | Bayer Ag | N-fenil-n-aminouracilas substituídas e seus sais, bem como seu uso como substâncias ativas herbicidas |
| US20220289708A1 (en) | 2019-07-22 | 2022-09-15 | Bayer Aktiengesellschaft | Substituted n-phenyl uracils, salts thereof and their use as herbicidal agents |
| EP4038054A1 (en) | 2019-10-01 | 2022-08-10 | Bayer Aktiengesellschaft | Pyrimidinedione derivatives |
| JP7785754B2 (ja) | 2020-08-24 | 2025-12-15 | バイエル、アクチエンゲゼルシャフト | 置換ｎ－フェニルウラシルおよびその塩、ならびに除草活性物質としてのその使用 |
| EP4230620A1 (de) | 2022-02-22 | 2023-08-23 | Bayer Aktiengesellschaft | Substituierte n-amino-n´-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2023161172A1 (de) | 2022-02-22 | 2023-08-31 | Bayer Aktiengesellschaft | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| EP4230621A1 (de) | 2022-02-22 | 2023-08-23 | Bayer AG | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| AR130967A1 (es) | 2022-11-16 | 2025-02-05 | Bayer Ag | Cicloalquilsulfanilfeniluracilos sustituidos, así como sus sales y su uso como principios activos herbicidas |
| AR131018A1 (es) | 2022-11-16 | 2025-02-12 | Bayer Ag | Cicloalquiloxifeniluracilos sustituidos, así como sus sales y su uso como principios activos herbicidas |
| AR131017A1 (es) | 2022-11-16 | 2025-02-12 | Bayer Ag | Ciclopropiloxifeniluracilos sustituidos, así como sus sales y su uso como principios activos herbicidas |
| AR134261A1 (es) | 2023-11-15 | 2025-12-17 | Bayer Ag | Oxiiminometilfeniluracilos sustituidos, así como sus sales y su uso como principios activos herbicidas |
| WO2025103929A1 (de) | 2023-11-15 | 2025-05-22 | Bayer Aktiengesellschaft | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2025103931A1 (de) | 2023-11-15 | 2025-05-22 | Bayer Aktiengesellschaft | Substituierte cyclopropyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084084A (en) * | 1989-07-14 | 1992-01-28 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
| US5169430A (en) * | 1991-08-09 | 1992-12-08 | Uniroyal Chemical Company, Inc. | Benzenesulfonamide derivatives and methods for their production |
| JPH05125057A (ja) * | 1991-11-01 | 1993-05-21 | Sumitomo Chem Co Ltd | １−フエニル−４−トリフルオロメチルウラシル誘導体およびそれを有効成分とする除草剤 |
| CA2128232A1 (en) * | 1992-01-15 | 1993-07-22 | Kofi Sam Amuti | Herbicides for citrus, oil palm, rubber and other plantation crops |
| JPH06271409A (ja) * | 1993-03-18 | 1994-09-27 | Nissan Chem Ind Ltd | 除草剤組成物 |
| JPH0753313A (ja) * | 1993-08-13 | 1995-02-28 | Nissan Chem Ind Ltd | 除草剤組成物 |
| DE4412079A1 (de) * | 1993-08-18 | 1995-02-23 | Bayer Ag | N-Cyanoaryl-Stickstoffheterocyclen |
-
1994
- 1994-09-15 DE DE4432888A patent/DE4432888A1/de not_active Withdrawn
-
1995
- 1995-09-04 CN CN95195061A patent/CN1157552A/zh active Pending
- 1995-09-04 BR BR9508929A patent/BR9508929A/pt not_active Application Discontinuation
- 1995-09-04 EP EP95931983A patent/EP0781093A1/de not_active Withdrawn
- 1995-09-04 AU AU35213/95A patent/AU3521395A/en not_active Abandoned
- 1995-09-04 HU HU9701964A patent/HUT77013A/hu unknown
- 1995-09-04 WO PCT/EP1995/003472 patent/WO1996008151A1/de not_active Ceased
- 1995-09-04 JP JP8509868A patent/JPH10505603A/ja active Pending
- 1995-09-04 MX MX9701953A patent/MX9701953A/es unknown
- 1995-09-04 CA CA002199846A patent/CA2199846A1/en not_active Abandoned
-
1997
- 1997-03-12 KR KR19977001634A patent/KR970705924A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BR9508929A (pt) | 1998-01-06 |
| EP0781093A1 (de) | 1997-07-02 |
| WO1996008151A1 (de) | 1996-03-21 |
| KR970705924A (enExample) | 1997-11-03 |
| AU3521395A (en) | 1996-03-29 |
| DE4432888A1 (de) | 1996-03-21 |
| CA2199846A1 (en) | 1996-03-21 |
| CN1157552A (zh) | 1997-08-20 |
| MX9701953A (es) | 1997-06-28 |
| JPH10505603A (ja) | 1998-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DFA9 | Temporary prot. cancelled due to abandonment |