SK286364B6 - 4-(3-Heterocyklyl-1-benzoyl)pyrazoly, spôsob ich prípravy, kompozície s ich obsahom a ich použitie ako herbicídov - Google Patents

4-(3-Heterocyklyl-1-benzoyl)pyrazoly, spôsob ich prípravy, kompozície s ich obsahom a ich použitie ako herbicídov Download PDF

Info

Publication number: SK286364B6
Authority: SK; Slovakia
Prior art keywords: compounds; differ; particularly preferred; methyl; ethyl
Prior art date: 1997-01-17

Application number

SK919-99A

Other languages

English (en)

Slovak (sk)

Other versions

SK91999A3 (en

Inventor

Deyn Wolfgang Von

Regina Luise Hill

Ernst Baumann

Stefan Engel

Guido Mayer

Joachim Rheinheimer

Matthias Witschel

Ulf Misslitz

Oliver Wagner

Martina Otten

Helmut Walter

Karl-Otto Westphalen

Original Assignee

Basf Aktiengesellschaft

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-01-17

Filing date

1998-01-08

Publication date

2008-08-05

1998-01-08 Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft

2000-01-18 Publication of SK91999A3 publication Critical patent/SK91999A3/sk

2008-08-05 Publication of SK286364B6 publication Critical patent/SK286364B6/sk

Links

239000000203 mixture Substances 0.000 title claims abstract description 71
238000000034 method Methods 0.000 title claims abstract description 22
150000003217 pyrazoles Chemical class 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 8
239000004009 herbicide Substances 0.000 title claims description 7
150000003839 salts Chemical class 0.000 claims abstract description 17
125000001424 substituent group Chemical group 0.000 claims abstract description 11
150000001875 compounds Chemical class 0.000 claims description 1808
-1 C 1 -C 6 -alkyl Chemical group 0.000 claims description 1465
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 34
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 32
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
229910052757 nitrogen Chemical group 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 7
125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
238000009472 formulation Methods 0.000 claims description 5
125000005842 heteroatom Chemical group 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000000460 chlorine Substances 0.000 description 366
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 336
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 216
229910052801 chlorine Inorganic materials 0.000 description 180
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 176
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 60
125000006125 ethylsulfonyl group Chemical group 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 38
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 35
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 35
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 32
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 21
229910052794 bromium Inorganic materials 0.000 description 20
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
239000012074 organic phase Substances 0.000 description 18
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
241000196324 Embryophyta Species 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 16
238000010992 reflux Methods 0.000 description 16
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 15
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 14
239000003921 oil Substances 0.000 description 14
238000006467 substitution reaction Methods 0.000 description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002585 base Substances 0.000 description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
230000002363 herbicidal effect Effects 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 11
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 11
125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
125000000623 heterocyclic group Chemical group 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
150000001299 aldehydes Chemical class 0.000 description 9
239000011737 fluorine Substances 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-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
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
239000007787 solid Substances 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
244000038559 crop plants Species 0.000 description 7
125000001153 fluoro group Chemical group F* 0.000 description 7
150000002825 nitriles Chemical class 0.000 description 7
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000006185 dispersion Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
150000008041 alkali metal carbonates Chemical class 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000005997 bromomethyl group Chemical group 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
238000011282 treatment Methods 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
241000499489 Castor canadensis Species 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
235000011779 Menyanthes trifoliata Nutrition 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
150000001266 acyl halides Chemical class 0.000 description 4
150000001345 alkine derivatives Chemical class 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000011065 in-situ storage Methods 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
CINZMASDNYKHEX-UHFFFAOYSA-N methyl 2-chloro-3-(hydroxyiminomethyl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=NO)=C1Cl CINZMASDNYKHEX-UHFFFAOYSA-N 0.000 description 4
VZAPQVDWIVCLDU-UHFFFAOYSA-N methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=O)=C1Cl VZAPQVDWIVCLDU-UHFFFAOYSA-N 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
229910000029 sodium carbonate Inorganic materials 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
ZSHNSXSONOHWNB-UHFFFAOYSA-N 1-(2-chloro-3-methyl-4-methylsulfanylphenyl)ethanone Chemical compound CSC1=CC=C(C(C)=O)C(Cl)=C1C ZSHNSXSONOHWNB-UHFFFAOYSA-N 0.000 description 3
125000006118 1-ethylbutyl sulfinyl group Chemical group 0.000 description 3
WPZFIPFTZJIAGG-UHFFFAOYSA-N 2,4-dichloro-3-(3-methyl-1,2-oxazol-5-yl)benzoic acid Chemical compound O1N=C(C)C=C1C1=C(Cl)C=CC(C(O)=O)=C1Cl WPZFIPFTZJIAGG-UHFFFAOYSA-N 0.000 description 3
OEBSDCJYCNVUCY-UHFFFAOYSA-N 2-chloro-3-(4,4-dimethyl-5h-1,3-oxazol-2-yl)-4-methylsulfonylbenzoic acid Chemical compound CC1(C)COC(C=2C(=CC=C(C=2Cl)C(O)=O)S(C)(=O)=O)=N1 OEBSDCJYCNVUCY-UHFFFAOYSA-N 0.000 description 3
YUTLRRXZEZXEAY-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1C1=NOCC1 YUTLRRXZEZXEAY-UHFFFAOYSA-N 0.000 description 3
JURLTYXSZFLINT-UHFFFAOYSA-N 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoyl chloride Chemical compound CS(=O)(=O)C1=CC=C(C(Cl)=O)C(Cl)=C1C1=NOCC1 JURLTYXSZFLINT-UHFFFAOYSA-N 0.000 description 3
QRPLOBYIGXQKIO-UHFFFAOYSA-N 2-chloro-3-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoic acid Chemical compound O1C(C)CC(C=2C(=CC=C(C=2Cl)C(O)=O)S(C)(=O)=O)=N1 QRPLOBYIGXQKIO-UHFFFAOYSA-N 0.000 description 3
YJZLEZGVPBXZHL-UHFFFAOYSA-N 2-chloro-3-methoxycarbonyl-6-methylsulfonylbenzoic acid Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(O)=O)=C1Cl YJZLEZGVPBXZHL-UHFFFAOYSA-N 0.000 description 3
RRFGGUXLGOVPOP-UHFFFAOYSA-N 2-chloro-3-methyl-4-methylsulfonylbenzoic acid Chemical compound CC1=C(Cl)C(C(O)=O)=CC=C1S(C)(=O)=O RRFGGUXLGOVPOP-UHFFFAOYSA-N 0.000 description 3
JMARSTSWTFXHMC-UHFFFAOYSA-N 2-methyl-1h-pyrazol-3-one Chemical compound CN1NC=CC1=O JMARSTSWTFXHMC-UHFFFAOYSA-N 0.000 description 3
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 3
FCODLBLEKSFOLV-UHFFFAOYSA-N CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O FCODLBLEKSFOLV-UHFFFAOYSA-N 0.000 description 3
ARRSCTRGLYHRHX-UHFFFAOYSA-N Cc1cc(on1)-c1c(Cl)ccc(C(=O)c2cnn(C)c2O)c1Cl Chemical compound Cc1cc(on1)-c1c(Cl)ccc(C(=O)c2cnn(C)c2O)c1Cl ARRSCTRGLYHRHX-UHFFFAOYSA-N 0.000 description 3
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239000005977 Ethylene Substances 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
238000000297 Sandmeyer reaction Methods 0.000 description 3
239000005708 Sodium hypochlorite Substances 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
125000006350 alkyl thio alkyl group Chemical group 0.000 description 3
150000001448 anilines Chemical class 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
150000001558 benzoic acid derivatives Chemical class 0.000 description 3
238000009835 boiling Methods 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000000969 carrier Substances 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000004927 clay Substances 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
230000006378 damage Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
230000035784 germination Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 description 3
125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 3
QPFZUWFTBASOOI-UHFFFAOYSA-N methyl 2,4-dichloro-3-(3-hydroxyiminobut-1-enyl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=CC(C)=NO)=C1Cl QPFZUWFTBASOOI-UHFFFAOYSA-N 0.000 description 3
VNMZOUCPGKLXLB-UHFFFAOYSA-N methyl 2,4-dichloro-3-(3-oxobut-1-enyl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=CC(C)=O)=C1Cl VNMZOUCPGKLXLB-UHFFFAOYSA-N 0.000 description 3
CMHAHZIWNCFHFL-UHFFFAOYSA-N methyl 2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2CCON=2)=C1Cl CMHAHZIWNCFHFL-UHFFFAOYSA-N 0.000 description 3
BBWCBPYXCNCYAT-UHFFFAOYSA-N methyl 2-chloro-3-methyl-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C)=C1Cl BBWCBPYXCNCYAT-UHFFFAOYSA-N 0.000 description 3
YQYVOGFWLVVXMM-UHFFFAOYSA-N methyl 3-(bromomethyl)-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(CBr)=C1Cl YQYVOGFWLVVXMM-UHFFFAOYSA-N 0.000 description 3
GTXHAHDFJJTAKY-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(Cl)=O)=C1Cl GTXHAHDFJJTAKY-UHFFFAOYSA-N 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
239000011707 mineral Substances 0.000 description 3
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239000000376 reactant Substances 0.000 description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
241000894007 species Species 0.000 description 3
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125000004743 1-methylethoxycarbonyl group Chemical group CC(C)OC(=O)* 0.000 description 2
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NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
NYBQALQPGPWNMJ-UHFFFAOYSA-N 2-chloro-3-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoyl chloride Chemical compound O1C(C)CC(C=2C(=CC=C(C=2Cl)C(Cl)=O)S(C)(=O)=O)=N1 NYBQALQPGPWNMJ-UHFFFAOYSA-N 0.000 description 2
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125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 2
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical class CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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235000021533 Beta vulgaris Nutrition 0.000 description 2
241000335053 Beta vulgaris Species 0.000 description 2
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KEKWPUYGONZTKO-UHFFFAOYSA-N ClC1=C(C(=O)C=2C=NN(C2O)C)C=CC(=C1N1OCC(C1)(C)C)S(=O)(=O)C Chemical compound ClC1=C(C(=O)C=2C=NN(C2O)C)C=CC(=C1N1OCC(C1)(C)C)S(=O)(=O)C KEKWPUYGONZTKO-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
238000006736 Huisgen cycloaddition reaction Methods 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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240000006394 Sorghum bicolor Species 0.000 description 2
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235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
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240000008042 Zea mays Species 0.000 description 2
CLXQGRFDFDZFGI-UHFFFAOYSA-N [2-chloro-3-(4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylphenyl]-(1-ethyl-5-phenylmethoxypyrazol-4-yl)methanone Chemical compound C=1C=CC=CC=1COC=1N(CC)N=CC=1C(=O)C(C=1Cl)=CC=C(S(C)(=O)=O)C=1C1=NOCC1 CLXQGRFDFDZFGI-UHFFFAOYSA-N 0.000 description 2
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229910052784 alkaline earth metal Inorganic materials 0.000 description 2
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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
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OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000007942 carboxylates Chemical class 0.000 description 2
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125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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150000002366 halogen compounds Chemical class 0.000 description 2
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239000000543 intermediate Substances 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 2
150000002545 isoxazoles Chemical class 0.000 description 2
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 2
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229910052751 metal Inorganic materials 0.000 description 2
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WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
LVFVYGWMXYKCGM-UHFFFAOYSA-N methyl 2,4-dichloro-3-(3-methyl-1,2-oxazol-5-yl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=2ON=C(C)C=2)=C1Cl LVFVYGWMXYKCGM-UHFFFAOYSA-N 0.000 description 2
YYNDTSNUQWSZEY-UHFFFAOYSA-N methyl 2,4-dichloro-3-formylbenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=O)=C1Cl YYNDTSNUQWSZEY-UHFFFAOYSA-N 0.000 description 2
SAROUWCFKNKRQQ-UHFFFAOYSA-N methyl 2-chloro-3-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2CC(C)ON=2)=C1Cl SAROUWCFKNKRQQ-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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238000007254 oxidation reaction Methods 0.000 description 2
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WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
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125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
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125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
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AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
125000006251 butylcarbonyl group Chemical group 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
229910002091 carbon monoxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011280 coal tar Substances 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
108700041286 delta Proteins 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
125000004671 dialkylaminothiocarbonyl group Chemical group 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
150000004891 diazines Chemical class 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical group COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
LVXHNCUCBXIIPE-UHFFFAOYSA-L disodium;hydrogen phosphate;hydrate Chemical compound O.[Na+].[Na+].OP([O-])([O-])=O LVXHNCUCBXIIPE-UHFFFAOYSA-L 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
235000004426 flaxseed Nutrition 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
125000005817 fluorobutyl group Chemical group [H]C([H])(F)C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
238000010353 genetic engineering Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
125000000232 haloalkynyl group Chemical group 0.000 description 1
150000003977 halocarboxylic acids Chemical class 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
125000006343 heptafluoro propyl group Chemical group 0.000 description 1
150000004761 hexafluorosilicates Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004871 hexylcarbonyl group Chemical group C(CCCCC)C(=O)* 0.000 description 1
239000003864 humus Substances 0.000 description 1
YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 description 1
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 description 1
125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 1
VTDDAIQPBQJYSL-UHFFFAOYSA-N methyl 2,4-dichloro-3-(2-methoxyethenyl)benzoate Chemical compound COC=CC1=C(Cl)C=CC(C(=O)OC)=C1Cl VTDDAIQPBQJYSL-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 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
WNPVAXLJVUXYFU-UHFFFAOYSA-N n-cyclohex-2-en-1-ylidenehydroxylamine Chemical compound ON=C1CCCC=C1 WNPVAXLJVUXYFU-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000007855 nitrilimines Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
231100001184 nonphytotoxic Toxicity 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
229920002114 octoxynol-9 Polymers 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
125000000962 organic group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
238000007243 oxidative cyclization reaction Methods 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
UYMQWGLCXYHTES-UHFFFAOYSA-N phenyl(1h-pyrazol-5-yl)methanone Chemical class C=1C=CC=CC=1C(=O)C1=CC=NN1 UYMQWGLCXYHTES-UHFFFAOYSA-N 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
150000008048 phenylpyrazoles Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
125000004673 propylcarbonyl group Chemical group 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003219 pyrazolines Chemical class 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000004576 sand Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007659 semicarbazones Chemical class 0.000 description 1
238000007873 sieving Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
229960002218 sodium chlorite Drugs 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
XMVONEAAOPAGAO-UHFFFAOYSA-N sodium tungstate Chemical compound [Na+].[Na+].[O-][W]([O-])(=O)=O XMVONEAAOPAGAO-UHFFFAOYSA-N 0.000 description 1
PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
125000005537 sulfoxonium group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
239000011573 trace mineral Substances 0.000 description 1
235000013619 trace mineral Nutrition 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- 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
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
- 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
- C07D417/10—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 aromatic rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

SK919-99A 1997-01-17 1998-01-08 4-(3-Heterocyklyl-1-benzoyl)pyrazoly, spôsob ich prípravy, kompozície s ich obsahom a ich použitie ako herbicídov SK286364B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19701446		1997-01-17
DE19740494		1997-09-15
PCT/EP1998/000070 WO1998031682A1 (de)	1997-01-17	1998-01-08	4-(3-heterocyclyl-1-benzoyl)pyrazole und ihre verwendung als herbizide

Publications (2)

Publication Number	Publication Date
SK91999A3 SK91999A3 (en)	2000-01-18
SK286364B6 true SK286364B6 (sk)	2008-08-05

Family

ID=26033168

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Application Number	Title	Priority Date	Filing Date
SK919-99A SK286364B6 (sk)	1997-01-17	1998-01-08	4-(3-Heterocyklyl-1-benzoyl)pyrazoly, spôsob ich prípravy, kompozície s ich obsahom a ich použitie ako herbicídov

Country Status (31)

Country	Link
US (1)	US6165944A (es)
EP (1)	EP0958292B1 (es)
JP (1)	JP4259620B2 (es)
KR (2)	KR100571463B1 (es)
CN (1)	CN1104429C (es)
AR (1)	AR012836A1 (es)
AT (1)	ATE350380T1 (es)
AU (1)	AU742514B2 (es)
BG (1)	BG64389B1 (es)
BR (1)	BR9806917B1 (es)
CA (1)	CA2277893C (es)
CZ (1)	CZ298050B6 (es)
DE (1)	DE59813869D1 (es)
DK (1)	DK0958292T3 (es)
EA (1)	EA009338B1 (es)
EE (1)	EE05291B1 (es)
ES (1)	ES2279569T3 (es)
GE (1)	GEP20022765B (es)
HU (1)	HU226012B1 (es)
IL (1)	IL130778A0 (es)
MX (1)	MX209959B (es)
NO (1)	NO314728B1 (es)
NZ (1)	NZ336640A (es)
PL (1)	PL195943B1 (es)
PT (1)	PT958292E (es)
SI (1)	SI0958292T1 (es)
SK (1)	SK286364B6 (es)
TR (1)	TR199901665T2 (es)
TW (1)	TW513414B (es)
UA (1)	UA60325C2 (es)
WO (1)	WO1998031682A1 (es)

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AR032779A1 (es) *	2000-12-11	2003-11-26	Basf Ag	Derivados de ciclohexenona de benzazolonas, acidos benzazolonacarboxilicos, agentes que contienen por lo menos un derivado de ciclohexenona, procedimiento para combatir el crecimiento indeseado de plantas y uso de dichos derivados como herbicidas
BR0209099B1 (pt) *	2001-04-27	2013-04-24		composiÇço seletivamente herbicida e mÉtodo para controlar o desenvolvimento de plantas indesejadas em colheitas de plantas éteis.
CN1297543C (zh) *	2001-05-09	2007-01-31	拜尔农作物科学股份公司	取代的芳基酮类化合物
DE10136449A1 (de) *	2001-05-09	2002-11-14	Bayer Ag	Substituierte Arylketone
DE10138577A1 (de) *	2001-05-21	2002-11-28	Bayer Ag	Substituierte Benzoylpyrazole
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DE10142333A1 (de) *	2001-08-30	2003-03-20	Bayer Cropscience Ag	Herbizide Mischungen auf Basis von substituierten Arylketonen
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DE10209645A1 (de) *	2002-03-05	2003-09-18	Bayer Cropscience Ag	Substituierte Arylketone
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MXPA05000346A (es) *	2002-07-24	2005-03-31	Basf Ag	Mezclas herbicidas de accion sinergica.
UA94003C2 (uk) *	2006-11-28	2011-03-25	Ишихара Санджай Кайша, Лтд.	Сполуки бензоїлпіразолу, гербіцид на їх основі та спосіб боротьби з небажаними рослинами
MX2010005231A (es) *	2007-11-12	2010-05-27	Du Pont	Mezcla herbicida.
WO2011067184A1 (de)	2009-12-01	2011-06-09	Basf Se	3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazolverbindungen und ihre mischungen mit safenern
DK2921493T3 (da) *	2011-12-27	2017-11-27	Bayer Ip Gmbh	Heteroarylpiperidin og ¿piperazinderivater
CN105399674B (zh)	2015-12-31	2017-02-15	青岛清原化合物有限公司	吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CN105503728B (zh)	2015-12-31	2017-03-22	青岛清原化合物有限公司	吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CN107629046B (zh) *	2017-10-24	2021-07-06	青岛清原化合物有限公司	吡唑酮类化合物或其盐、除草剂组合物及用途
CN111285863B (zh) *	2018-12-07	2022-04-26	青岛清原化合物有限公司	4-(3-杂环基-1-苯甲酰基)吡唑类化合物或其盐、制备方法、除草剂组合物及用途
CA3154030C (en) *	2019-10-08	2024-02-27	Shenyang Sinochem Agrochemicals R&D Co., Ltd.	Alkene-containing carboxylic ester compound and application thereof
CN112624974B (zh) *	2019-10-08	2024-01-30	沈阳中化农药化工研发有限公司	一种肉桂羧酸酯类化合物及其应用
CN116120234B (zh) *	2021-11-15	2024-12-17	沈阳中化农药化工研发有限公司	一种苯甲酰吡唑类化合物及其应用
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1997
- 1997-01-08 US US09/091,292 patent/US6165944A/en not_active Expired - Fee Related
1998
- 1998-01-08 SK SK919-99A patent/SK286364B6/sk not_active IP Right Cessation
- 1998-01-08 DK DK98907930T patent/DK0958292T3/da active
- 1998-01-08 ES ES98907930T patent/ES2279569T3/es not_active Expired - Lifetime
- 1998-01-08 PL PL98334849A patent/PL195943B1/pl not_active IP Right Cessation
- 1998-01-08 KR KR19997006464A patent/KR100571463B1/ko not_active Expired - Fee Related
- 1998-01-08 CN CN98802992A patent/CN1104429C/zh not_active Expired - Fee Related
- 1998-01-08 DE DE59813869T patent/DE59813869D1/de not_active Expired - Lifetime
- 1998-01-08 EP EP98907930A patent/EP0958292B1/de not_active Expired - Lifetime
- 1998-01-08 WO PCT/EP1998/000070 patent/WO1998031682A1/de not_active Ceased
- 1998-01-08 JP JP53362198A patent/JP4259620B2/ja not_active Expired - Fee Related
- 1998-01-08 IL IL13077898A patent/IL130778A0/xx unknown
- 1998-01-08 EE EEP199900292A patent/EE05291B1/xx not_active IP Right Cessation
- 1998-01-08 NZ NZ336640A patent/NZ336640A/xx unknown
- 1998-01-08 HU HU0002178A patent/HU226012B1/hu not_active IP Right Cessation
- 1998-01-08 KR KR1020067003690A patent/KR20060025610A/ko not_active Ceased
- 1998-01-08 AT AT98907930T patent/ATE350380T1/de not_active IP Right Cessation
- 1998-01-08 SI SI9830875T patent/SI0958292T1/sl unknown
- 1998-01-08 TR TR1999/01665T patent/TR199901665T2/xx unknown
- 1998-01-08 BR BRPI9806917-9A patent/BR9806917B1/pt not_active IP Right Cessation
- 1998-01-08 CZ CZ0252299A patent/CZ298050B6/cs not_active IP Right Cessation
- 1998-01-08 MX MX9906600A patent/MX209959B/es not_active IP Right Cessation
- 1998-01-08 EA EA199900619A patent/EA009338B1/ru not_active IP Right Cessation
- 1998-01-08 CA CA002277893A patent/CA2277893C/en not_active Expired - Fee Related
- 1998-01-08 PT PT98907930T patent/PT958292E/pt unknown
- 1998-01-08 AU AU66133/98A patent/AU742514B2/en not_active Ceased
- 1998-01-08 GE GEAP19984962A patent/GEP20022765B/en unknown
- 1998-01-15 TW TW087100464A patent/TW513414B/zh not_active IP Right Cessation
- 1998-01-16 AR ARP980100214A patent/AR012836A1/es active IP Right Grant
- 1998-08-01 UA UA99084709A patent/UA60325C2/uk unknown
1999
- 1999-07-16 NO NO19993522A patent/NO314728B1/no not_active IP Right Cessation
- 1999-08-13 BG BG103663A patent/BG64389B1/bg unknown

Also Published As

Publication number	Publication date
EE05291B1 (et)	2010-04-15
CA2277893C (en)	2008-03-18
UA60325C2 (uk)	2003-10-15
SI0958292T1 (sl)	2007-06-30
CN1250447A (zh)	2000-04-12
IL130778A0 (en)	2001-01-28
PL334849A1 (en)	2000-03-27
MX9906600A (es)	1999-10-31
HU226012B1 (en)	2008-02-28
HUP0002178A2 (hu)	2000-09-28
AU742514B2 (en)	2002-01-03
KR20060025610A (ko)	2006-03-21
PT958292E (pt)	2007-04-30
WO1998031682A1 (de)	1998-07-23
NO314728B1 (no)	2003-05-12
BR9806917B1 (pt)	2010-08-24
CZ298050B6 (cs)	2007-06-06
DE59813869D1 (de)	2007-02-15
BG103663A (en)	2000-06-30
NO993522L (no)	1999-09-16
ES2279569T3 (es)	2007-08-16
HUP0002178A3 (en)	2002-01-28
AU6613398A (en)	1998-08-07
BG64389B1 (bg)	2004-12-30
MX209959B (es)	2002-08-26
JP2001508459A (ja)	2001-06-26
CN1104429C (zh)	2003-04-02
CA2277893A1 (en)	1998-07-23
EP0958292B1 (de)	2007-01-03
JP4259620B2 (ja)	2009-04-30
EP0958292A1 (de)	1999-11-24
EA009338B1 (ru)	2007-12-28
NZ336640A (en)	2001-03-30
CZ252299A3 (cs)	2000-05-17
NO993522D0 (no)	1999-07-16
EE9900292A (et)	2000-02-15
TR199901665T2 (xx)	1999-09-21
PL195943B1 (pl)	2007-11-30
EA199900619A1 (ru)	2000-04-24
BR9806917A (pt)	2000-04-18
KR20000070237A (ko)	2000-11-25
US6165944A (en)	2000-12-26
KR100571463B1 (ko)	2006-04-17
SK91999A3 (en)	2000-01-18
TW513414B (en)	2002-12-11
ATE350380T1 (de)	2007-01-15
AR012836A1 (es)	2000-11-22
DK0958292T3 (da)	2007-05-07
GEP20022765B (en)	2002-08-26

Publication	Publication Date	Title
EP0958292B1 (de)	2007-01-03	4-(3-heterocyclyl-1-benzoyl)pyrazole und ihre verwendung als herbizide
US9045465B1 (en)	2015-06-02	3-heterocyclyl-substituted benzoyl derivatives
AU781318B2 (en)	2005-05-19	3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole
US6645919B1 (en)	2003-11-11	3-(4,5-Dihydroisoxazol-5-yl)benzoylcyclohexenones and the use thereof as herbicides
US6613719B1 (en)	2003-09-02	3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles
EP1181295B1 (de)	2004-02-18	Tricyclische benzoylcyclohexandion-derivate
US6627581B1 (en)	2003-09-30	Cyclopropyl-anellated 3-(4,5-dihydroisoxazol-3-yl)-substituted benzoylpyrazoles
WO2001040200A1 (de)	2001-06-07	Herbizide 3-(4,5-dihydroisoxazol-3-yl)-substituierte benzoylcyclohexenonderivate
EP1181297A1 (de)	2002-02-27	Cyclohexenondioxothiochromanoyl-derivate
EP1237881A1 (de)	2002-09-11	Herbizide halogenalkyl-substituierte 3-(4,5-dihydroisoxazol-3-yl)-benzoyl-cyclohexenone

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Date	Code	Title	Description
2011-10-04	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20110108