SK24498A3 - Pyrazol-4-yl-benzoyl derivatives and their use as herbicides - Google Patents
Pyrazol-4-yl-benzoyl derivatives and their use as herbicides Download PDFInfo
- Publication number
- SK24498A3 SK24498A3 SK244-98A SK24498A SK24498A3 SK 24498 A3 SK24498 A3 SK 24498A3 SK 24498 A SK24498 A SK 24498A SK 24498 A3 SK24498 A3 SK 24498A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- alkoxy
- haloalkyl
- haloalkoxy
- nitro
- Prior art date
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- -1 Pyrazol-4-yl-benzoyl Chemical class 0.000 title claims abstract description 200
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 58
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 47
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 46
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 22
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 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 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 claims description 3
- JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 claims description 3
- 230000008635 plant growth Effects 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 150000003217 pyrazoles Chemical class 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims 1
- YDZNRNHKJQTGCG-UHFFFAOYSA-N 1,1'-binaphthyl-2,2'-dicarboxylic acid Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C(=O)O)=C(C(O)=O)C=CC2=C1 YDZNRNHKJQTGCG-UHFFFAOYSA-N 0.000 claims 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
- 230000008569 process Effects 0.000 abstract description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 450
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 26
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 23
- 239000000243 solution Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 239000013543 active substance Substances 0.000 description 18
- 239000002585 base Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
- 239000012074 organic phase Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 150000001559 benzoic acids Chemical class 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- 229910000288 alkali metal carbonate Chemical group 0.000 description 6
- 150000008041 alkali metal carbonates Chemical group 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 4
- YILVFRPLXNUYCA-UHFFFAOYSA-N 8-methyl-4-oxo-2,3-dihydrothiochromene-7-carboxylic acid Chemical compound O=C1CCSC2=C1C=CC(C(O)=O)=C2C YILVFRPLXNUYCA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000010410 dusting Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- IRQFRKNADKZQSZ-UHFFFAOYSA-N 2-(3-methoxycarbonyl-2-methylphenyl)sulfanylacetic acid Chemical compound COC(=O)C1=CC=CC(SCC(O)=O)=C1C IRQFRKNADKZQSZ-UHFFFAOYSA-N 0.000 description 3
- NKFBPTSCHPREPV-UHFFFAOYSA-N 4-ethoxy-8-methyl-3,4-dihydro-2h-thiochromene-7-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(OCC)CCSC2=C1C NKFBPTSCHPREPV-UHFFFAOYSA-N 0.000 description 3
- KRLQCJBHIKIAKW-UHFFFAOYSA-N CC(C(S(CCC(O)=O)(=O)=O)=CC=C1)=C1C(OC)=O Chemical compound CC(C(S(CCC(O)=O)(=O)=O)=CC=C1)=C1C(OC)=O KRLQCJBHIKIAKW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
- 125000004104 aryloxy 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
- 238000009835 boiling Methods 0.000 description 3
- 238000006473 carboxylation reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- QYYGYIVPHNTANQ-UHFFFAOYSA-N methyl 8-methyl-4-oxo-2,3-dihydrothiochromene-7-carboxylate Chemical compound O=C1CCSC2=C(C)C(C(=O)OC)=CC=C21 QYYGYIVPHNTANQ-UHFFFAOYSA-N 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 150000003003 phosphines Chemical group 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 2
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 2
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 2
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- QFVTYMBTYBQZDK-UHFFFAOYSA-N 4-ethoxy-8-methyl-1,1-dioxo-3,4-dihydro-2h-thiochromene-7-carboxylic acid Chemical compound OC(=O)C1=CC=C2C(OCC)CCS(=O)(=O)C2=C1C QFVTYMBTYBQZDK-UHFFFAOYSA-N 0.000 description 2
- UGAGBVWICDGBAO-UHFFFAOYSA-N 8-methyl-1,4-dioxo-2,3-dihydrothiochromene-7-carboxylic acid Chemical compound O=C1CCS(=O)C2=C1C=CC(C(O)=O)=C2C UGAGBVWICDGBAO-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000021533 Beta vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- XLAXFAWXVYQINK-UHFFFAOYSA-N Cc1nn(C)c(O)c1C(=O)c1ccc2C(=O)CCS(=O)(=O)c2c1C Chemical compound Cc1nn(C)c(O)c1C(=O)c1ccc2C(=O)CCS(=O)(=O)c2c1C XLAXFAWXVYQINK-UHFFFAOYSA-N 0.000 description 2
- 241000219312 Chenopodium Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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- 239000005909 Kieselgur Substances 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 101150003085 Pdcl gene Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 235000007244 Zea mays Nutrition 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 150000003918 triazines Chemical class 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19532312A DE19532312A1 (de) | 1995-09-01 | 1995-09-01 | Pyrazol-4-yl-benzoylderivate |
| PCT/EP1996/003794 WO1997009327A1 (fr) | 1995-09-01 | 1996-08-29 | Derives de pyrazol-4-yl-benzoyle et leur utilisation comme herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK24498A3 true SK24498A3 (en) | 1998-11-04 |
Family
ID=7771030
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK244-98A SK24498A3 (en) | 1995-09-01 | 1996-08-29 | Pyrazol-4-yl-benzoyl derivatives and their use as herbicides |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6291682B1 (fr) |
| EP (1) | EP0961774B1 (fr) |
| JP (1) | JPH11512105A (fr) |
| KR (1) | KR19990044328A (fr) |
| CN (1) | CN1071756C (fr) |
| AR (1) | AR004949A1 (fr) |
| AT (1) | ATE210660T1 (fr) |
| AU (1) | AU710278B2 (fr) |
| BR (1) | BR9610210A (fr) |
| CA (1) | CA2227946A1 (fr) |
| CZ (1) | CZ60298A3 (fr) |
| DE (2) | DE19532312A1 (fr) |
| DK (1) | DK0961774T3 (fr) |
| EA (1) | EA000753B1 (fr) |
| EE (1) | EE03614B1 (fr) |
| ES (1) | ES2169808T3 (fr) |
| GE (1) | GEP20022677B (fr) |
| HU (1) | HUP9802345A3 (fr) |
| IL (1) | IL123092A (fr) |
| MX (1) | MX9801289A (fr) |
| NZ (1) | NZ316941A (fr) |
| PL (1) | PL325279A1 (fr) |
| PT (1) | PT961774E (fr) |
| SK (1) | SK24498A3 (fr) |
| TR (1) | TR199800345T1 (fr) |
| TW (1) | TW325474B (fr) |
| WO (1) | WO1997009327A1 (fr) |
| ZA (1) | ZA967357B (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA51645C2 (uk) * | 1995-02-13 | 2002-12-16 | Ідеміцу Козан Ко., Лтд | Похідні піразолу, проміжні сполуки для їх одержання та гербіцид на їх основі |
| WO1999059991A1 (fr) * | 1998-05-18 | 1999-11-25 | Basf Aktiengesellschaft | Derives du type pyrazolyldioxothiochromanoyle |
| WO2000034271A1 (fr) * | 1998-12-04 | 2000-06-15 | Basf Aktiengesellschaft | Procede pour la production de derives de pyrazolylbenzoyle, ainsi que nouveaux derives de pyrazolylbenzoyle |
| EP1135385A1 (fr) | 1998-12-04 | 2001-09-26 | Basf Aktiengesellschaft | Derives de thiochromanoylpyrazolone |
| AU4562000A (en) * | 1999-05-07 | 2000-11-21 | Basf Aktiengesellschaft | 4-(3',4'-heterocyclyl benzoyl) pyrazoles as herbicidal agents |
| AR031786A1 (es) * | 2000-12-11 | 2003-10-01 | Basf Ag | 5-((pirazol-4-il)carbonil)benzazolonas |
| EP2127521A1 (fr) * | 2008-05-29 | 2009-12-02 | Bayer CropScience Aktiengesellschaft | 4-(3-Alkylsulfinylbenzoyl)pyrazole actifs en tant qu'herbicide |
| EP2892885A1 (fr) | 2012-09-05 | 2015-07-15 | Bayer CropScience AG | Amides d'acide bicycloarylcarboxylique à action herbicide |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4986845A (en) * | 1988-07-15 | 1991-01-22 | Nissan Chemical Industries Ltd. | Pyrazole derivatives and herbicides containing them |
| WO1993015060A1 (fr) * | 1992-01-22 | 1993-08-05 | Nissan Chemical Industries, Ltd. | Derive de pyrazole substitue et bactericide agrohorticole |
| BR9306011A (pt) * | 1992-03-03 | 1997-10-21 | Idemitsu Kosan Co | Derivados de pirazol |
| JP3210670B2 (ja) * | 1992-07-13 | 2001-09-17 | 出光興産株式会社 | ピラゾール誘導体 |
| US5607898A (en) | 1993-08-02 | 1997-03-04 | Idemitsu Kosan Company, Ltd. | Pyrazole derivatives |
-
1995
- 1995-09-01 DE DE19532312A patent/DE19532312A1/de not_active Withdrawn
-
1996
- 1996-08-27 TW TW085110390A patent/TW325474B/zh active
- 1996-08-29 EP EP96930126A patent/EP0961774B1/fr not_active Expired - Lifetime
- 1996-08-29 DE DE59608472T patent/DE59608472D1/de not_active Expired - Fee Related
- 1996-08-29 AU AU69296/96A patent/AU710278B2/en not_active Ceased
- 1996-08-29 IL IL12309296A patent/IL123092A/en not_active IP Right Cessation
- 1996-08-29 EA EA199800234A patent/EA000753B1/ru not_active IP Right Cessation
- 1996-08-29 CN CN96196605A patent/CN1071756C/zh not_active Expired - Fee Related
- 1996-08-29 EE EE9800054A patent/EE03614B1/xx not_active IP Right Cessation
- 1996-08-29 CA CA002227946A patent/CA2227946A1/fr not_active Abandoned
- 1996-08-29 WO PCT/EP1996/003794 patent/WO1997009327A1/fr not_active Application Discontinuation
- 1996-08-29 ES ES96930126T patent/ES2169808T3/es not_active Expired - Lifetime
- 1996-08-29 HU HU9802345A patent/HUP9802345A3/hu unknown
- 1996-08-29 US US09/029,124 patent/US6291682B1/en not_active Expired - Fee Related
- 1996-08-29 MX MX9801289A patent/MX9801289A/es unknown
- 1996-08-29 DK DK96930126T patent/DK0961774T3/da active
- 1996-08-29 GE GEAP19964210A patent/GEP20022677B/en unknown
- 1996-08-29 TR TR1998/00345T patent/TR199800345T1/xx unknown
- 1996-08-29 CZ CZ98602A patent/CZ60298A3/cs unknown
- 1996-08-29 PL PL96325279A patent/PL325279A1/xx unknown
- 1996-08-29 JP JP9510831A patent/JPH11512105A/ja not_active Withdrawn
- 1996-08-29 NZ NZ316941A patent/NZ316941A/xx unknown
- 1996-08-29 PT PT96930126T patent/PT961774E/pt unknown
- 1996-08-29 KR KR1019980701568A patent/KR19990044328A/ko not_active Ceased
- 1996-08-29 SK SK244-98A patent/SK24498A3/sk unknown
- 1996-08-29 BR BR9610210A patent/BR9610210A/pt not_active IP Right Cessation
- 1996-08-29 AT AT96930126T patent/ATE210660T1/de not_active IP Right Cessation
- 1996-08-30 ZA ZA9607357A patent/ZA967357B/xx unknown
- 1996-08-30 AR ARP960104183A patent/AR004949A1/es not_active Application Discontinuation
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