CH629364A5 - Herbizides mittel. - Google Patents
Herbizides mittel. Download PDFInfo
- Publication number
- CH629364A5 CH629364A5 CH1417475A CH1417475A CH629364A5 CH 629364 A5 CH629364 A5 CH 629364A5 CH 1417475 A CH1417475 A CH 1417475A CH 1417475 A CH1417475 A CH 1417475A CH 629364 A5 CH629364 A5 CH 629364A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenylpyrazole
- acetamide
- analysis
- found
- carbon atoms
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 573
- 150000001875 compounds Chemical class 0.000 claims description 152
- -1 alkoxy radical Chemical class 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 65
- 239000004480 active ingredient Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 description 180
- 238000004458 analytical method Methods 0.000 description 170
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 81
- 239000000460 chlorine Substances 0.000 description 80
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 64
- LANBPXHLIUYXOT-UHFFFAOYSA-N 4-methyl-5-phenyl-1h-pyrazole Chemical compound C1=NNC(C=2C=CC=CC=2)=C1C LANBPXHLIUYXOT-UHFFFAOYSA-N 0.000 description 55
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 28
- 229940080818 propionamide Drugs 0.000 description 27
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 22
- 229910052794 bromium Inorganic materials 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
- WDOAUKIEENWZNC-UHFFFAOYSA-N 2-chloro-n,n-dimethylpropanamide Chemical compound CC(Cl)C(=O)N(C)C WDOAUKIEENWZNC-UHFFFAOYSA-N 0.000 description 20
- 238000009472 formulation Methods 0.000 description 19
- 239000003921 oil Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000007788 liquid Substances 0.000 description 16
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical group 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000007921 spray Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- NNWWOIPEHSLORU-UHFFFAOYSA-N 2-bromo-n,n-dimethylbutanamide Chemical compound CCC(Br)C(=O)N(C)C NNWWOIPEHSLORU-UHFFFAOYSA-N 0.000 description 10
- SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- CNUHUXQSZVLAGL-UHFFFAOYSA-N 2-bromo-n,n,2-trimethylpropanamide Chemical compound CN(C)C(=O)C(C)(C)Br CNUHUXQSZVLAGL-UHFFFAOYSA-N 0.000 description 7
- PTGHHGHHFPDNBR-UHFFFAOYSA-N 2-pyrazol-1-ylacetamide Chemical compound NC(=O)CN1C=CC=N1 PTGHHGHHFPDNBR-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 5
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 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 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 5
- 239000010455 vermiculite Substances 0.000 description 5
- 229910052902 vermiculite Inorganic materials 0.000 description 5
- 235000019354 vermiculite Nutrition 0.000 description 5
- GRKIAPNDYIKCBO-UHFFFAOYSA-N 5-(2-chlorophenyl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2C(=CC=CC=2)Cl)=C1C GRKIAPNDYIKCBO-UHFFFAOYSA-N 0.000 description 4
- QQYICHGCQZYYOQ-UHFFFAOYSA-N 5-(furan-2-yl)-4-methyl-1h-pyrazole Chemical compound C1=NNC(C=2OC=CC=2)=C1C QQYICHGCQZYYOQ-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229960001413 acetanilide Drugs 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000000428 dust Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052622 kaolinite Inorganic materials 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- WORKHWHULFDZDE-UHFFFAOYSA-N 2-chloro-n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)C(C)Cl WORKHWHULFDZDE-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- ICURQXROMAKEGX-UHFFFAOYSA-N 4-methyl-5-thiophen-2-yl-1h-pyrazole Chemical compound C1=NNC(C=2SC=CC=2)=C1C ICURQXROMAKEGX-UHFFFAOYSA-N 0.000 description 3
- DWBQZNMWKPXWEK-UHFFFAOYSA-N 5-(2-chlorophenyl)-1h-pyrazole Chemical compound ClC1=CC=CC=C1C1=CC=NN1 DWBQZNMWKPXWEK-UHFFFAOYSA-N 0.000 description 3
- ULGVTFHMCLFGSU-UHFFFAOYSA-N 5-(2-methylphenyl)-1h-pyrazole Chemical compound CC1=CC=CC=C1C1=CC=NN1 ULGVTFHMCLFGSU-UHFFFAOYSA-N 0.000 description 3
- QHRSESMSOJZMCO-UHFFFAOYSA-N 5-methyl-3-phenyl-1h-pyrazole Chemical compound N1C(C)=CC(C=2C=CC=CC=2)=N1 QHRSESMSOJZMCO-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229910052903 pyrophyllite Inorganic materials 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 150000003871 sulfonates Chemical class 0.000 description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- GTSMGKYOGFOSAR-UHFFFAOYSA-N tridecane-1-sulfonic acid Chemical compound CCCCCCCCCCCCCS(O)(=O)=O GTSMGKYOGFOSAR-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 2
- NGLXUWPQWYFICX-UHFFFAOYSA-N 2,3-dibromo-n,n-dimethylpropanamide Chemical compound CN(C)C(=O)C(Br)CBr NGLXUWPQWYFICX-UHFFFAOYSA-N 0.000 description 2
- GXSNDPGJEZZSAK-UHFFFAOYSA-N 2-(3-phenylpyrazol-1-yl)acetamide Chemical compound NC(=O)CN1C=CC(C=2C=CC=CC=2)=N1 GXSNDPGJEZZSAK-UHFFFAOYSA-N 0.000 description 2
- RSTGBTUVISMDCM-UHFFFAOYSA-N 2-bromo-n,n-dimethylpentanamide Chemical compound CCCC(Br)C(=O)N(C)C RSTGBTUVISMDCM-UHFFFAOYSA-N 0.000 description 2
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 2
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- XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
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- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
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- 235000009566 rice Nutrition 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- SMBZJSVIKJMSFP-UHFFFAOYSA-N trifluoromethyl hypofluorite Chemical compound FOC(F)(F)F SMBZJSVIKJMSFP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
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Classifications
-
- 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
- C07D231/16—Halogen atoms or nitro radicals
-
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52423174A | 1974-11-15 | 1974-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH629364A5 true CH629364A5 (de) | 1982-04-30 |
Family
ID=24088332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1417475A CH629364A5 (de) | 1974-11-15 | 1975-11-03 | Herbizides mittel. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4072498A (https=) |
| JP (1) | JPS5182269A (https=) |
| BE (1) | BE835604A (https=) |
| BR (1) | BR7507364A (https=) |
| CH (1) | CH629364A5 (https=) |
| DE (1) | DE2550566A1 (https=) |
| FR (1) | FR2324633A1 (https=) |
| GB (1) | GB1483162A (https=) |
| IT (1) | IT1052194B (https=) |
| NZ (1) | NZ178996A (https=) |
| PH (1) | PH12819A (https=) |
| PL (1) | PL101829B1 (https=) |
| SU (2) | SU613722A3 (https=) |
| ZA (1) | ZA756627B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019081477A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2019081485A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2901593A1 (de) * | 1979-01-17 | 1980-08-07 | Basf Ag | N-azolylessigsaeureanilide |
| DE3041702A1 (de) * | 1980-11-05 | 1982-06-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur bekaempfung unerwuenschten pflanzenwuchses mit 2-aryloxy-2-azolylalkancarbonsaeureamiden, diese enthaltende herbizide und verfahren zu ihrer herstellung |
| US4515623A (en) * | 1981-10-09 | 1985-05-07 | Basf Aktiengesellschaft | Control of unwanted plant growth with 2-aryloxy-2-azolylalkanecarboxamides |
| US4874871A (en) * | 1987-03-25 | 1989-10-17 | Syntex (U.S.A.) Inc. | Process for preparing (+)-2,3-Dihydro-1H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid and related compounds |
| US4870095A (en) * | 1988-06-13 | 1989-09-26 | Sterling Drug, Inc. | 1H-pyrazole-1-alkanamides, antiarrhythmic compositions and use |
| JP2784925B2 (ja) * | 1988-09-07 | 1998-08-13 | 日本農薬株式会社 | ３又は５−フェニルピラゾール類又はその塩及び除草剤 |
| US4916150A (en) * | 1989-03-22 | 1990-04-10 | Sterling Drug Inc. | 1H-pyrazole-1-alkanamines antiarrhythmic compositions and use |
| US4988725A (en) * | 1989-03-22 | 1991-01-29 | Sterling Drug Inc. | 1H-pyrazole-1-(branched)alkanamides as antiarrhythmic agents, compositions and use |
| US4898880A (en) * | 1989-03-22 | 1990-02-06 | Sterling Drug Inc. | N-(heterocycle)alkyl)-1H-pyrazole-1-alkanamides as antiarrhythmic agents, compositions and use |
| US4888352A (en) * | 1989-03-22 | 1989-12-19 | Sterling Drug Inc. | 3,4, or 5-aryl-1H-pyrazole-1-alkanamides as antiarrhythmic agents, compositions and use |
| US4925857A (en) * | 1989-03-22 | 1990-05-15 | Sterling Drug Inc. | Pyridinyl-1H-pyrazole-1-alkanamides as antiarrhythmic agents |
| US4994482A (en) * | 1989-07-31 | 1991-02-19 | Bristol-Myers Squibb Company | Arylpyrazol derivatives as anti-platelet agents, compositions and use |
| JPH0393774A (ja) * | 1989-09-07 | 1991-04-18 | Nippon Nohyaku Co Ltd | ３又は５―フェニルピラゾール類又はその塩及び除草剤 |
| US5366987A (en) * | 1991-08-22 | 1994-11-22 | Warner-Lambert Company | Isoxazolyl-substituted alkyl amide ACAT inhibitors |
| US5532416A (en) * | 1994-07-20 | 1996-07-02 | Monsanto Company | Benzoyl derivatives and synthesis thereof |
| FR2682379B1 (fr) | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
| FR2690440B1 (fr) * | 1992-04-27 | 1995-05-19 | Rhone Poulenc Agrochimie | Arylpyrazoles fongicides. |
| IL112014A (en) * | 1993-12-24 | 1999-10-28 | Rhone Poulenc Agrochimie | 1,3-Oxazin-4-one derivatives and herbicides containing the same |
| US5880290A (en) * | 1994-01-31 | 1999-03-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US5869688A (en) * | 1994-07-20 | 1999-02-09 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| US5698708A (en) * | 1996-06-20 | 1997-12-16 | Monsanto Company | Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity |
| DE19744026A1 (de) * | 1997-10-06 | 1999-04-08 | Hoechst Marion Roussel De Gmbh | Pyrazol-Derivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| CA2368631A1 (en) | 1999-03-26 | 2000-10-05 | Euro-Celtique S.A. | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof |
| NZ520875A (en) | 2000-03-24 | 2005-04-29 | Euro Celtique S | Aryl substituted pyrazoles, triazoles and tetrazoles as sodium channel blocker |
| JP4430938B2 (ja) * | 2001-12-20 | 2010-03-10 | 株式会社エス・ディー・エス バイオテック | 新規置換ピラゾール誘導体、その製造方法およびそれらを含有する除草剤組成物 |
| CN103265537B (zh) * | 2013-05-14 | 2015-05-27 | 浙江医药高等专科学校 | 抗肿瘤化合物、其制备方法和用途 |
| GB201616439D0 (en) * | 2016-09-28 | 2016-11-09 | Mironid Limited | Compounds and uses |
| GB201805527D0 (en) | 2018-04-04 | 2018-05-16 | Mironid Ltd | Compounds and their use as pde4 activators |
| CN110963957B (zh) | 2018-09-28 | 2021-10-22 | 深圳恩多凯医药科技有限公司 | N-芳香酰胺类化合物及其制备方法和用途 |
| CN119019332B (zh) * | 2024-08-15 | 2026-02-24 | 赣南师范大学 | 一种1,5-二取代-4-溴吡唑类化合物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH485733A (de) * | 1967-04-26 | 1970-02-15 | Agripat Sa | Verfahren zur Herstellung halogensubstituierter Imidazol-Derivate |
| BE795881A (fr) * | 1972-02-23 | 1973-08-23 | Upjohn Co | Tribromopyrazoles et leur preparation |
-
1975
- 1975-10-20 NZ NZ178996A patent/NZ178996A/xx unknown
- 1975-10-21 ZA ZA756627A patent/ZA756627B/xx unknown
- 1975-10-23 GB GB43505/75A patent/GB1483162A/en not_active Expired
- 1975-11-03 CH CH1417475A patent/CH629364A5/de not_active IP Right Cessation
- 1975-11-07 BR BR7507364*A patent/BR7507364A/pt unknown
- 1975-11-11 DE DE19752550566 patent/DE2550566A1/de not_active Withdrawn
- 1975-11-14 FR FR7534913A patent/FR2324633A1/fr not_active Withdrawn
- 1975-11-14 IT IT52221/75A patent/IT1052194B/it active
- 1975-11-14 SU SU752189715A patent/SU613722A3/ru active
- 1975-11-14 SU SU7502190909A patent/SU581838A3/ru active
- 1975-11-14 BE BE161900A patent/BE835604A/xx unknown
- 1975-11-15 JP JP50137708A patent/JPS5182269A/ja active Pending
- 1975-11-15 PL PL1975184782A patent/PL101829B1/pl unknown
-
1976
- 1976-05-14 US US05/686,548 patent/US4072498A/en not_active Expired - Lifetime
-
1977
- 1977-11-23 PH PH20469A patent/PH12819A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019081477A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
| WO2019081485A1 (de) | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
Also Published As
| Publication number | Publication date |
|---|---|
| AU8595775A (en) | 1977-04-28 |
| JPS5182269A (https=) | 1976-07-19 |
| IT1052194B (it) | 1981-06-20 |
| PL101829B1 (pl) | 1979-02-28 |
| DE2550566A1 (de) | 1976-05-20 |
| FR2324633A1 (fr) | 1977-04-15 |
| SU613722A3 (ru) | 1978-06-30 |
| ZA756627B (en) | 1977-05-25 |
| BR7507364A (pt) | 1976-08-10 |
| US4072498A (en) | 1978-02-07 |
| PH12819A (en) | 1979-08-31 |
| NZ178996A (en) | 1978-06-02 |
| GB1483162A (en) | 1977-08-17 |
| BE835604A (fr) | 1976-05-14 |
| SU581838A3 (ru) | 1977-11-25 |
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| PL | Patent ceased | ||
| PL | Patent ceased |