HRP940053A2 - New 4-benzoylysoxazole derivatives, process for the preparation thereof, compositions containing them and their use as herbicides - Google Patents
New 4-benzoylysoxazole derivatives, process for the preparation thereof, compositions containing them and their use as herbicides Download PDFInfo
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- HRP940053A2 HRP940053A2 HR9302072.5A HRP940053A HRP940053A2 HR P940053 A2 HRP940053 A2 HR P940053A2 HR P940053 A HRP940053 A HR P940053A HR P940053 A2 HRP940053 A2 HR P940053A2
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- alkyl group
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- 239000000203 mixture Substances 0.000 title claims description 69
- 238000000034 method Methods 0.000 title claims description 16
- 239000004009 herbicide Substances 0.000 title description 10
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 105
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 241000196324 Embryophyta Species 0.000 claims description 47
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 230000002363 herbicidal effect Effects 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 16
- 239000004094 surface-active agent Substances 0.000 claims description 16
- -1 CO2R5 Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
- 235000008504 concentrate Nutrition 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 235000014666 liquid concentrate Nutrition 0.000 claims description 5
- FGGUUGIYSOGQED-UHFFFAOYSA-N 1,2-oxazol-4-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=NOC=1 FGGUUGIYSOGQED-UHFFFAOYSA-N 0.000 claims description 4
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 2
- GWVASMIDAYRKGJ-UHFFFAOYSA-N [2-(5-ethyl-1,2-oxazole-4-carbonyl)phenyl] methanesulfonate Chemical compound O1N=CC(C(=O)C=2C(=CC=CC=2)OS(C)(=O)=O)=C1CC GWVASMIDAYRKGJ-UHFFFAOYSA-N 0.000 claims description 2
- APKOXORUPOBMLT-UHFFFAOYSA-N [4-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(Cl)C=C1C(=O)C1=C(C2CC2)ON=C1 APKOXORUPOBMLT-UHFFFAOYSA-N 0.000 claims description 2
- BNZNMTJDQHRTMV-UHFFFAOYSA-N [5-chloro-2-(5-cyclopropyl-1,2-oxazole-4-carbonyl)phenyl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 BNZNMTJDQHRTMV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 125000002524 organometallic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012442 inert solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 150000002545 isoxazoles Chemical class 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 239000011149 active material Substances 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- AIWQBGVRLYEWRN-UHFFFAOYSA-N 2-(dimethylsulfamoyloxy)benzoic acid Chemical compound CN(C)S(=O)(=O)OC1=CC=CC=C1C(O)=O AIWQBGVRLYEWRN-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
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- 240000005702 Galium aparine Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
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- 241001506766 Xanthium Species 0.000 description 2
- FFBYEEKKQBGXKG-UHFFFAOYSA-N [3-chloro-4-[2-(cyclopropanecarbonyl)-3-ethoxyprop-2-enoyl]phenyl] methanesulfonate Chemical compound C=1C=C(OS(C)(=O)=O)C=C(Cl)C=1C(=O)C(=COCC)C(=O)C1CC1 FFBYEEKKQBGXKG-UHFFFAOYSA-N 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- 238000010790 dilution Methods 0.000 description 2
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- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
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- 150000003460 sulfonic acids Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- BAWKKLHWPPTOQM-UHFFFAOYSA-N (4-carbonochloridoyl-3-chlorophenyl) methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=C(C(Cl)=O)C(Cl)=C1 BAWKKLHWPPTOQM-UHFFFAOYSA-N 0.000 description 1
- MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
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- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
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- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
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- LZBOSTUKSJTISB-UHFFFAOYSA-N 2-methylsulfonyloxybenzoic acid Chemical compound CS(=O)(=O)OC1=CC=CC=C1C(O)=O LZBOSTUKSJTISB-UHFFFAOYSA-N 0.000 description 1
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- OGBMKADBTDQDQT-UHFFFAOYSA-N 4-chloro-2-methylsulfonyloxybenzoic acid Chemical compound CS(=O)(=O)OC1=CC(Cl)=CC=C1C(O)=O OGBMKADBTDQDQT-UHFFFAOYSA-N 0.000 description 1
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- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
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- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- RBNIGDFIUWJJEV-UHFFFAOYSA-N methyl 2-(n-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical group C=1C=C(F)C(Cl)=CC=1N(C(C)C(=O)OC)C(=O)C1=CC=CC=C1 RBNIGDFIUWJJEV-UHFFFAOYSA-N 0.000 description 1
- DAGHNACWRJYCHW-UHFFFAOYSA-N methyl 2-ethylsulfonyloxybenzoate Chemical compound CCS(=O)(=O)OC1=CC=CC=C1C(=O)OC DAGHNACWRJYCHW-UHFFFAOYSA-N 0.000 description 1
- RRYYFUQICXOSKE-UHFFFAOYSA-N methyl 2-methylsulfonyloxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OS(C)(=O)=O RRYYFUQICXOSKE-UHFFFAOYSA-N 0.000 description 1
- XFAKXDZKHZFEGQ-UHFFFAOYSA-N methyl 4-chloro-2-methylsulfonyloxybenzoate Chemical compound COC(=O)C1=CC=C(Cl)C=C1OS(C)(=O)=O XFAKXDZKHZFEGQ-UHFFFAOYSA-N 0.000 description 1
- QMVOMVWQAUCZSZ-UHFFFAOYSA-N methyl 5-chloro-2-methylsulfonyloxybenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1OS(C)(=O)=O QMVOMVWQAUCZSZ-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- RGUOJYYIMVSCNC-UHFFFAOYSA-N n,n-dimethylformamide;2-methylpropanoic acid Chemical compound CN(C)C=O.CC(C)C(O)=O RGUOJYYIMVSCNC-UHFFFAOYSA-N 0.000 description 1
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CXPRGLWJJQBWRS-UHFFFAOYSA-N tert-butyl 3-cyclopropyl-3-oxopropanoate Chemical compound CC(C)(C)OC(=O)CC(=O)C1CC1 CXPRGLWJJQBWRS-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939302072A GB9302072D0 (en) | 1993-02-03 | 1993-02-03 | New compositions of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP940053A2 true HRP940053A2 (en) | 1996-10-31 |
Family
ID=10729751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR9302072.5A HRP940053A2 (en) | 1993-02-03 | 1994-02-01 | New 4-benzoylysoxazole derivatives, process for the preparation thereof, compositions containing them and their use as herbicides |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5371063A (xx) |
| EP (1) | EP0609797A1 (xx) |
| JP (1) | JPH06271553A (xx) |
| KR (1) | KR940019698A (xx) |
| CN (1) | CN1093359A (xx) |
| AP (1) | AP436A (xx) |
| AU (1) | AU671330B2 (xx) |
| BG (1) | BG98435A (xx) |
| BR (1) | BR9400233A (xx) |
| CA (1) | CA2114897A1 (xx) |
| CZ (1) | CZ21994A3 (xx) |
| FI (1) | FI940483A (xx) |
| GB (1) | GB9302072D0 (xx) |
| HR (1) | HRP940053A2 (xx) |
| HU (1) | HUT66521A (xx) |
| IL (1) | IL108502A (xx) |
| MA (1) | MA23101A1 (xx) |
| NZ (1) | NZ250807A (xx) |
| PL (1) | PL302120A1 (xx) |
| RO (1) | RO112726B1 (xx) |
| SI (1) | SI9400058A (xx) |
| SK (1) | SK10894A3 (xx) |
| TR (1) | TR27449A (xx) |
| TW (1) | TW248521B (xx) |
| VN (1) | VN274A1 (xx) |
| YU (1) | YU5394A (xx) |
| ZA (1) | ZA94741B (xx) |
| ZW (1) | ZW994A1 (xx) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5627131A (en) * | 1995-01-09 | 1997-05-06 | Zeneca Limited | Herbicidal compositions of 4-benzoylisoxazole and antidotes therefor |
| EP0810999B1 (de) * | 1995-02-24 | 2000-01-12 | Basf Aktiengesellschaft | Isoxazolyl-benzoylderivate |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
| DE19614856A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch anellierte Benzoylisothiazole |
| DE19614858A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch substituierte Benzoylisothiazole |
| DE19614859A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide Benzoylisothiazole |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| US5863865A (en) * | 1997-10-28 | 1999-01-26 | Zeneca Limited | Herbicidal 4-benzoylisoxazoles derivatives |
| US5905057A (en) * | 1997-11-06 | 1999-05-18 | Rhone-Poulenc Agrochimie | Herbicidal 4-benzoylisoxazole-3-carboxylate liquid compositions comprising N-alkylpyrrolidinone stabilizer |
| CA2372500A1 (en) | 1999-04-27 | 2000-11-02 | Basf Aktiengesellschaft | Phosphoric benzoyl derivatives and their use as herbicides |
| DE19920791A1 (de) * | 1999-05-06 | 2000-11-09 | Bayer Ag | Substituierte Benzoylisoxazole |
| DE19946853A1 (de) | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
| CN1509285A (zh) * | 2000-01-17 | 2004-06-30 | 被取代的芳基酮类 | |
| DE10037149A1 (de) * | 2000-07-29 | 2002-02-07 | Bayer Ag | Substituierte Arylketone |
| US7112554B2 (en) * | 2001-05-09 | 2006-09-26 | Bayer Cropscience Ag | Substituted arylketones |
| DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
| DE10206792A1 (de) * | 2002-02-19 | 2003-08-28 | Bayer Cropscience Ag | Substituierte Arylketone |
| DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
| GB9025469D0 (en) * | 1990-11-22 | 1991-01-09 | Rhone Poulenc Agriculture | New compositions of matter |
| IL102674A (en) * | 1991-08-05 | 1996-11-14 | Rhone Poulenc Agriculture | History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the same |
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
| US5334753A (en) * | 1992-03-12 | 1994-08-02 | Rhone-Poulenc Agriculture Ltd | Processes for preparing ortho-substituted benzoic acids |
| GB9215551D0 (en) * | 1992-07-22 | 1992-09-02 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9302049D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | Compositions of new matter |
-
1993
- 1993-02-03 GB GB939302072A patent/GB9302072D0/en active Pending
-
1994
- 1994-01-27 MA MA23407A patent/MA23101A1/fr unknown
- 1994-01-28 BR BR9400233A patent/BR9400233A/pt not_active Application Discontinuation
- 1994-01-31 AU AU54798/94A patent/AU671330B2/en not_active Ceased
- 1994-01-31 IL IL108502A patent/IL108502A/xx not_active IP Right Cessation
- 1994-01-31 EP EP94101364A patent/EP0609797A1/en not_active Withdrawn
- 1994-01-31 VN VNS-690/94A patent/VN274A1/vi unknown
- 1994-02-01 CZ CZ94219A patent/CZ21994A3/cs unknown
- 1994-02-01 HR HR9302072.5A patent/HRP940053A2/hr not_active Application Discontinuation
- 1994-02-01 SK SK108-94A patent/SK10894A3/sk unknown
- 1994-02-02 YU YU5394A patent/YU5394A/sh unknown
- 1994-02-02 PL PL94302120A patent/PL302120A1/xx unknown
- 1994-02-02 RO RO94-00159A patent/RO112726B1/ro unknown
- 1994-02-02 FI FI940483A patent/FI940483A/fi not_active Application Discontinuation
- 1994-02-02 BG BG98435A patent/BG98435A/bg unknown
- 1994-02-02 ZW ZW994A patent/ZW994A1/xx unknown
- 1994-02-02 NZ NZ250807A patent/NZ250807A/en unknown
- 1994-02-02 HU HU9400287A patent/HUT66521A/hu unknown
- 1994-02-02 TR TR00078/94A patent/TR27449A/xx unknown
- 1994-02-03 AP APAP/P/1994/000616A patent/AP436A/en active
- 1994-02-03 SI SI9400058A patent/SI9400058A/sl unknown
- 1994-02-03 CA CA002114897A patent/CA2114897A1/en not_active Abandoned
- 1994-02-03 JP JP6011679A patent/JPH06271553A/ja active Pending
- 1994-02-03 US US08/191,449 patent/US5371063A/en not_active Expired - Fee Related
- 1994-02-03 KR KR1019940002032A patent/KR940019698A/ko not_active Application Discontinuation
- 1994-02-03 CN CN94101673A patent/CN1093359A/zh active Pending
- 1994-02-03 ZA ZA94741A patent/ZA94741B/xx unknown
- 1994-02-16 TW TW083101223A patent/TW248521B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| BR9400233A (pt) | 1994-10-04 |
| SK10894A3 (en) | 1994-12-07 |
| YU5394A (sh) | 1996-10-18 |
| IL108502A (en) | 1997-09-30 |
| TW248521B (xx) | 1995-06-01 |
| CZ21994A3 (en) | 1994-08-17 |
| VN274A1 (en) | 1996-09-25 |
| MA23101A1 (fr) | 1994-10-01 |
| CA2114897A1 (en) | 1994-08-04 |
| ZW994A1 (en) | 1994-08-03 |
| AU671330B2 (en) | 1996-08-22 |
| AU5479894A (en) | 1994-08-11 |
| KR940019698A (ko) | 1994-09-14 |
| HUT66521A (en) | 1994-12-28 |
| BG98435A (bg) | 1994-01-03 |
| FI940483A0 (fi) | 1994-02-02 |
| NZ250807A (en) | 1995-07-26 |
| GB9302072D0 (en) | 1993-03-24 |
| IL108502A0 (en) | 1994-05-30 |
| RO112726B1 (ro) | 1997-12-30 |
| ZA94741B (en) | 1994-09-29 |
| SI9400058A (en) | 1994-09-30 |
| FI940483A (fi) | 1994-08-04 |
| AP9400616A0 (en) | 1994-04-30 |
| HU9400287D0 (en) | 1994-05-30 |
| PL302120A1 (en) | 1994-08-08 |
| AP436A (en) | 1995-11-17 |
| CN1093359A (zh) | 1994-10-12 |
| US5371063A (en) | 1994-12-06 |
| EP0609797A1 (en) | 1994-08-10 |
| TR27449A (tr) | 1995-05-24 |
| JPH06271553A (ja) | 1994-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |