NO314728B1 - 4-(3-heterocyclyl-1-benzoyl)pyrazoler og anvendelse og fremstilling samt preparat og metode for kontroll av uönsket vegetasjon - Google Patents
4-(3-heterocyclyl-1-benzoyl)pyrazoler og anvendelse og fremstilling samt preparat og metode for kontroll av uönsket vegetasjon Download PDFInfo
- Publication number
- NO314728B1 NO314728B1 NO19993522A NO993522A NO314728B1 NO 314728 B1 NO314728 B1 NO 314728B1 NO 19993522 A NO19993522 A NO 19993522A NO 993522 A NO993522 A NO 993522A NO 314728 B1 NO314728 B1 NO 314728B1
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- differ
- methyl
- similarly
- particularly preferred
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 20
- 150000003217 pyrazoles Chemical class 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 1931
- -1 cyano, hydroxyl Chemical group 0.000 claims description 402
- 239000001257 hydrogen Substances 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 31
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000005048 dihydroisoxazolyl group Chemical group O1N(CC=C1)* 0.000 claims description 10
- 125000005050 dihydrooxazolyl group Chemical group O1C(NC=C1)* 0.000 claims description 10
- 125000005056 dihydrothiazolyl group Chemical group S1C(NC=C1)* 0.000 claims description 10
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000335 thiazolyl group Chemical group 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000011814 protection agent Substances 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000532 dioxanyl group Chemical group 0.000 claims description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 351
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 235
- 239000000460 chlorine Substances 0.000 description 170
- 229910052801 chlorine Inorganic materials 0.000 description 169
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 92
- 239000000203 mixture Substances 0.000 description 76
- 125000001309 chloro group Chemical group Cl* 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 47
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 45
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 40
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 39
- 239000002904 solvent Substances 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 27
- 238000010992 reflux Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 24
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 24
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 16
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 15
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 13
- 239000002585 base Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 230000002363 herbicidal effect Effects 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 9
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 150000002825 nitriles Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- JMARSTSWTFXHMC-UHFFFAOYSA-N 2-methyl-1h-pyrazol-3-one Chemical compound CN1NC=CC1=O JMARSTSWTFXHMC-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 244000038559 crop plants Species 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 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 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 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 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 150000001266 acyl halides Chemical class 0.000 description 4
- 150000001345 alkine derivatives Chemical class 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000007789 gas Substances 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
- 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
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052723 transition metal Inorganic materials 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
- 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
- WNCMNUAJUSHIFG-UHFFFAOYSA-N 2,4-dichloro-3-(3-propyl-1,2,4-oxadiazol-5-yl)benzoic acid Chemical compound CCCC1=NOC(C=2C(=C(C(O)=O)C=CC=2Cl)Cl)=N1 WNCMNUAJUSHIFG-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
- 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
- KZRWIDYURGXENQ-UHFFFAOYSA-N 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoic acid Chemical compound CS(=O)(=O)C1=CC=C(C(O)=O)C(Cl)=C1C1=NN=CO1 KZRWIDYURGXENQ-UHFFFAOYSA-N 0.000 description 3
- IREHAROUXNPLAT-UHFFFAOYSA-N 2-hydroxyethyl 3-(5-acetyl-1h-pyrazol-3-yl)-2,4-dichlorobenzoate Chemical compound N1N=C(C(=O)C)C=C1C1=C(Cl)C=CC(C(=O)OCCO)=C1Cl IREHAROUXNPLAT-UHFFFAOYSA-N 0.000 description 3
- AFRAKRBCARZHDH-UHFFFAOYSA-N 3-(5-acetyl-1h-pyrazol-3-yl)-2,4-dichlorobenzoic acid Chemical compound N1N=C(C(=O)C)C=C1C1=C(Cl)C=CC(C(O)=O)=C1Cl AFRAKRBCARZHDH-UHFFFAOYSA-N 0.000 description 3
- OZWWCHDWCROLME-UHFFFAOYSA-N 3-(5-acetyl-2-methylpyrazol-3-yl)-2,4-dichlorobenzoic acid Chemical compound CN1N=C(C(=O)C)C=C1C1=C(Cl)C=CC(C(O)=O)=C1Cl OZWWCHDWCROLME-UHFFFAOYSA-N 0.000 description 3
- FKSDXXMIVZPAHZ-UHFFFAOYSA-N CCn1ncc(C(=O)c2ccc(Cl)c(-c3cc(nn3C)C(C)=O)c2Cl)c1O Chemical compound CCn1ncc(C(=O)c2ccc(Cl)c(-c3cc(nn3C)C(C)=O)c2Cl)c1O FKSDXXMIVZPAHZ-UHFFFAOYSA-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
- CTOIQFOQJUYTQY-UHFFFAOYSA-N ClC1=C(C(=O)C=2C=NN(C2O)C)C=CC(=C1C1=NC(=NO1)CCC)Cl Chemical compound ClC1=C(C(=O)C=2C=NN(C2O)C)C=CC(=C1C1=NC(=NO1)CCC)Cl CTOIQFOQJUYTQY-UHFFFAOYSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- JHRZDTPXKBWUST-UHFFFAOYSA-N O1C(C)CC(C=2C(=CC=C(C=2Cl)C(=O)C2=C(N(C)N=C2)O)S(C)(=O)=O)=N1 Chemical compound O1C(C)CC(C=2C(=CC=C(C=2Cl)C(=O)C2=C(N(C)N=C2)O)S(C)(=O)=O)=N1 JHRZDTPXKBWUST-UHFFFAOYSA-N 0.000 description 3
- 238000000297 Sandmeyer reaction Methods 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001336 alkenes Chemical class 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
- 235000010233 benzoic acid Nutrition 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
- 239000000969 carrier Substances 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 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 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
- 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 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
- NJASBJCZHQZBML-UHFFFAOYSA-N methyl 2,4-dichloro-3-(3-propyl-1,2,4-oxadiazol-5-yl)benzoate Chemical compound CCCC1=NOC(C=2C(=C(C(=O)OC)C=CC=2Cl)Cl)=N1 NJASBJCZHQZBML-UHFFFAOYSA-N 0.000 description 3
- 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 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
- SSTUMMRNBCBEJW-UHFFFAOYSA-N methyl 2-chloro-3-(hydrazinecarbonyl)-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(=O)NN)=C1Cl SSTUMMRNBCBEJW-UHFFFAOYSA-N 0.000 description 3
- 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 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
- PVDBECGBEPNSDO-UHFFFAOYSA-N methyl 2-chloro-4-methylsulfonyl-3-(2-oxo-1,3,4-oxathiazol-5-yl)benzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2OC(=O)SN=2)=C1Cl PVDBECGBEPNSDO-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
- CUNGURJSPXCIRB-UHFFFAOYSA-N methyl 3-carbamoyl-2-chloro-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(N)=O)=C1Cl CUNGURJSPXCIRB-UHFFFAOYSA-N 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 230000008707 rearrangement Effects 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
- 150000003556 thioamides Chemical class 0.000 description 3
- CLKJPPYOVFJVSV-UHFFFAOYSA-N (2-ethylpyrazol-3-yl) 3-(5-acetyl-2-methylpyrazol-3-yl)-2,4-dichlorobenzoate Chemical compound CCN1N=CC=C1OC(=O)C1=CC=C(Cl)C(C=2N(N=C(C=2)C(C)=O)C)=C1Cl CLKJPPYOVFJVSV-UHFFFAOYSA-N 0.000 description 2
- DHMSRDWEFUZUJQ-UHFFFAOYSA-N 2,4-dichloro-3-(3-methyl-1,2-oxazol-5-yl)benzoyl chloride Chemical compound O1N=C(C)C=C1C1=C(Cl)C=CC(C(Cl)=O)=C1Cl DHMSRDWEFUZUJQ-UHFFFAOYSA-N 0.000 description 2
- VFNYZDRGDQOWIF-UHFFFAOYSA-N 2,4-dichloro-3-(3-propyl-1,2,4-oxadiazol-5-yl)benzoyl chloride Chemical compound CCCC1=NOC(C=2C(=C(C(Cl)=O)C=CC=2Cl)Cl)=N1 VFNYZDRGDQOWIF-UHFFFAOYSA-N 0.000 description 2
- NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 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
- 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 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 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
- 239000005995 Aluminium silicate Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 235000021533 Beta vulgaris Nutrition 0.000 description 2
- 241000335053 Beta vulgaris Species 0.000 description 2
- QFGNQGRUMNDUBY-UHFFFAOYSA-N CN1N=CC(C(=O)C=2C(=C(C=3OCC(C)(C)N=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CN1N=CC(C(=O)C=2C(=C(C=3OCC(C)(C)N=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O QFGNQGRUMNDUBY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 244000299507 Gossypium hirsutum Species 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000003973 alkyl amines Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000005228 aryl sulfonate group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 150000008359 benzonitriles Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 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 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
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 125000003106 haloaryl group Chemical group 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 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
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- ZHCKQNYRGDSWNQ-UHFFFAOYSA-N methyl 2,4-dichloro-3-[[(4-methylphenyl)sulfonylhydrazinylidene]methyl]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C=NNS(=O)(=O)C=2C=CC(C)=CC=2)=C1Cl ZHCKQNYRGDSWNQ-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
- UJKWSMALIPPINA-UHFFFAOYSA-N methyl 2-chloro-4-methylsulfonyl-3-(1,3,4-oxadiazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C=2OC=NN=2)=C1Cl UJKWSMALIPPINA-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- USVVENVKYJZFMW-ONEGZZNKSA-N (e)-carboxyiminocarbamic acid Chemical class OC(=O)\N=N\C(O)=O USVVENVKYJZFMW-ONEGZZNKSA-N 0.000 description 1
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- QNMYJMZVOFQIRD-UHFFFAOYSA-N 1-chloro-2-methyl-3-methylsulfanylbenzene Chemical compound CSC1=CC=CC(Cl)=C1C QNMYJMZVOFQIRD-UHFFFAOYSA-N 0.000 description 1
- LZVOHXBKNVKJGZ-UHFFFAOYSA-N 1-chloro-2-methyl-3-methylsulfonylbenzene Chemical compound CC1=C(Cl)C=CC=C1S(C)(=O)=O LZVOHXBKNVKJGZ-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical class OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- QZEDXQFZACVDJE-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 QZEDXQFZACVDJE-UHFFFAOYSA-N 0.000 description 1
- CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
- MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KLGTXQOZQXTQPQ-UHFFFAOYSA-N 2-benzyl-1,2-oxazolidin-3-one Chemical class O=C1CCON1CC1=CC=CC=C1 KLGTXQOZQXTQPQ-UHFFFAOYSA-N 0.000 description 1
- IRVOAFSCLMOJBF-UHFFFAOYSA-N 2-chloro-3-[(1-chloro-2-methylpropan-2-yl)carbamoyl]-4-methylsulfonylbenzoyl chloride Chemical compound ClCC(C)(C)NC(=O)C1=C(Cl)C(C(Cl)=O)=CC=C1S(C)(=O)=O IRVOAFSCLMOJBF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SZHVXHIOPADPJI-UHFFFAOYSA-N 2-chloro-4-methyl-3-(5-methyl-4,5-dihydro-1,2-oxazol-3-yl)benzoyl chloride Chemical compound O1C(C)CC(C=2C(=C(C(Cl)=O)C=CC=2C)Cl)=N1 SZHVXHIOPADPJI-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- QZVRXWBKQJFSLP-UHFFFAOYSA-N 2-ethyl-1h-pyrazol-3-one Chemical compound CCN1NC=CC1=O QZVRXWBKQJFSLP-UHFFFAOYSA-N 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- WIISOYLZJJYTHT-UHFFFAOYSA-N 2-methyl-1h-pyrazol-5-one Chemical compound CN1C=CC(O)=N1 WIISOYLZJJYTHT-UHFFFAOYSA-N 0.000 description 1
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 description 1
- XAMZZEBAJZJERT-UHFFFAOYSA-M 2-oxopropyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)C)C1=CC=CC=C1 XAMZZEBAJZJERT-UHFFFAOYSA-M 0.000 description 1
- QBGQIMOGHUXVKB-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class O=C1C(CCCC2)=C2C(=O)N1C1=CC=CC=C1 QBGQIMOGHUXVKB-UHFFFAOYSA-N 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 235000005255 Allium cepa Nutrition 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 235000011446 Amygdalus persica Nutrition 0.000 description 1
- 244000099147 Ananas comosus Species 0.000 description 1
- 235000007119 Ananas comosus Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 244000060924 Brassica campestris Species 0.000 description 1
- 235000005637 Brassica campestris Nutrition 0.000 description 1
- 244000178924 Brassica napobrassica Species 0.000 description 1
- 235000011297 Brassica napobrassica Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- IUCXCDBYRBQAJD-UHFFFAOYSA-N CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O Chemical compound CCN1N=CC(C(=O)C=2C(=C(C=3CCON=3)C(=CC=2)S(C)(=O)=O)Cl)=C1O IUCXCDBYRBQAJD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000052707 Camellia sinensis Species 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 244000068645 Carya illinoensis Species 0.000 description 1
- 235000009025 Carya illinoensis Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 235000007460 Coffea arabica Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000228031 Coffea liberica Species 0.000 description 1
- 244000016593 Coffea robusta Species 0.000 description 1
- 235000002187 Coffea robusta Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 240000003133 Elaeis guineensis Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 235000016623 Fragaria vesca Nutrition 0.000 description 1
- 244000307700 Fragaria vesca Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000014751 Gossypium arboreum Nutrition 0.000 description 1
- 240000001814 Gossypium arboreum Species 0.000 description 1
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
- 238000007341 Heck reaction Methods 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 241000208134 Nicotiana rustica Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 1
- 235000002725 Olea europaea Nutrition 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 244000100170 Phaseolus lunatus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 244000193463 Picea excelsa Species 0.000 description 1
- 235000008124 Picea excelsa Nutrition 0.000 description 1
- 235000005205 Pinus Nutrition 0.000 description 1
- 241000218602 Pinus <genus> Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 244000007021 Prunus avium Species 0.000 description 1
- 235000010401 Prunus avium Nutrition 0.000 description 1
- 240000005809 Prunus persica Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 241001506137 Rapa Species 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000016911 Ribes sativum Nutrition 0.000 description 1
- 240000000528 Ricinus communis Species 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 238000005609 Rosenmund-von Braun cyanation reaction Methods 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000007230 Sorghum bicolor Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 206010044278 Trace element deficiency Diseases 0.000 description 1
- 235000015724 Trifolium pratense Nutrition 0.000 description 1
- 240000002913 Trifolium pratense Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005575 aldol reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 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
- XUMDNHCCUNPEEY-UHFFFAOYSA-N bis(2-hydroxyethylidene)azanium Chemical compound OCC=[N+]=CCO XUMDNHCCUNPEEY-UHFFFAOYSA-N 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- XRGPFNGLRSIPSA-UHFFFAOYSA-N butyn-2-one Chemical compound CC(=O)C#C XRGPFNGLRSIPSA-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 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
- 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
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 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
- 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
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 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
- 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
- 239000002283 diesel fuel Substances 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
- ZHXTWWCDMUWMDI-UHFFFAOYSA-N dihydroxyboron Chemical compound O[B]O ZHXTWWCDMUWMDI-UHFFFAOYSA-N 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 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
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 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
- 238000009472 formulation Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000002532 grape seed extract Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000003977 halocarboxylic acids Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000004761 hexafluorosilicates Chemical class 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
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 description 1
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 description 1
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid 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
- 235000009973 maize Nutrition 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
- MSDQAKYIAGOKSJ-UHFFFAOYSA-N methyl 2,4-dichloro-3-(2-oxoethyl)benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(CC=O)=C1Cl MSDQAKYIAGOKSJ-UHFFFAOYSA-N 0.000 description 1
- RPTPNNYELMAGMG-UHFFFAOYSA-N methyl 2-chloro-3-[(1-hydroxy-2-methylpropan-2-yl)carbamoyl]-4-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(S(C)(=O)=O)C(C(=O)NC(C)(C)CO)=C1Cl RPTPNNYELMAGMG-UHFFFAOYSA-N 0.000 description 1
- QYNPWZZIEKLZJM-UHFFFAOYSA-N methyl 3-carbonochloridoyl-2,4-dichlorobenzoate Chemical compound COC(=O)C1=CC=C(Cl)C(C(Cl)=O)=C1Cl QYNPWZZIEKLZJM-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 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
- 150000007855 nitrilimines Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 235000015097 nutrients Nutrition 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
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000004866 oxadiazoles Chemical class 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 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
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003880 polar aprotic solvent 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 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
- 238000001953 recrystallisation Methods 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
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- MNOALXGAYUJNKX-UHFFFAOYSA-N s-chloro chloromethanethioate Chemical compound ClSC(Cl)=O MNOALXGAYUJNKX-UHFFFAOYSA-N 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
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 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
- 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
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 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
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 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
- 239000004562 water dispersible granule 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
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 (3)
| Publication Number | Publication Date |
|---|---|
| NO993522D0 NO993522D0 (no) | 1999-07-16 |
| NO993522L NO993522L (no) | 1999-09-16 |
| NO314728B1 true NO314728B1 (no) | 2003-05-12 |
Family
ID=26033168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993522A NO314728B1 (no) | 1997-01-17 | 1999-07-16 | 4-(3-heterocyclyl-1-benzoyl)pyrazoler og anvendelse og fremstilling samt preparat og metode for kontroll av uönsket vegetasjon |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6165944A (cs) |
| EP (1) | EP0958292B1 (cs) |
| JP (1) | JP4259620B2 (cs) |
| KR (2) | KR100571463B1 (cs) |
| CN (1) | CN1104429C (cs) |
| AR (1) | AR012836A1 (cs) |
| AT (1) | ATE350380T1 (cs) |
| AU (1) | AU742514B2 (cs) |
| BG (1) | BG64389B1 (cs) |
| BR (1) | BR9806917B1 (cs) |
| CA (1) | CA2277893C (cs) |
| CZ (1) | CZ298050B6 (cs) |
| DE (1) | DE59813869D1 (cs) |
| DK (1) | DK0958292T3 (cs) |
| EA (1) | EA009338B1 (cs) |
| EE (1) | EE05291B1 (cs) |
| ES (1) | ES2279569T3 (cs) |
| GE (1) | GEP20022765B (cs) |
| HU (1) | HU226012B1 (cs) |
| IL (1) | IL130778A0 (cs) |
| MX (1) | MX209959B (cs) |
| NO (1) | NO314728B1 (cs) |
| NZ (1) | NZ336640A (cs) |
| PL (1) | PL195943B1 (cs) |
| PT (1) | PT958292E (cs) |
| SI (1) | SI0958292T1 (cs) |
| SK (1) | SK286364B6 (cs) |
| TR (1) | TR199901665T2 (cs) |
| TW (1) | TW513414B (cs) |
| UA (1) | UA60325C2 (cs) |
| WO (1) | WO1998031682A1 (cs) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0891972A4 (en) * | 1996-03-26 | 2000-12-13 | Nippon Soda Co | SUBSTITUTED BENZOIC ACID DERIVATIVES 3- (ISOXAZOL-5-YL) AND PROCESS FOR PRODUCING THE SAME |
| BR9806778B1 (pt) * | 1997-01-17 | 2009-12-01 | derivado de benzoìla substituìda por 3-heterociclila, composto, processo para a preparação do dito derivado de benzoìla substituìda por 3-heterociclila, derivado de ácido benzóico substituìdo por 3-heterociclila, composição e uso do referido derivado de benzoìla substutuìda por 3-heterociclila. | |
| AU9647998A (en) * | 1997-10-27 | 1999-05-17 | Nippon Soda Co., Ltd. | Novel benzoylpyrazole derivatives and herbicides |
| US6147031A (en) * | 1997-10-30 | 2000-11-14 | Nippon Soda Co., Ltd. | Benzoylpyrazole compounds, intermediate preparing therefor and herbicides |
| CA2727762C (en) * | 1998-05-11 | 2013-09-10 | Basf Aktiengesellschaft | Process for synthesizing thioether precursors of herbicides by reaction of anilines with dialkyl disulfides in the presence of an alkyl nitrite |
| DE19846792A1 (de) * | 1998-10-10 | 2000-04-13 | Hoechst Schering Agrevo Gmbh | Benzoylcyclohexandione, Verfahren zur ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| ATE249456T1 (de) | 1998-12-04 | 2003-09-15 | Basf Ag | 3-(heterocyclyl)-substituierte benzoylpyrazole |
| CN1332739A (zh) * | 1998-12-04 | 2002-01-23 | 巴斯福股份公司 | 3－(杂环基)苯甲酰基吡唑衍生物 |
| DE19914140A1 (de) * | 1999-03-27 | 2000-09-28 | Bayer Ag | Substituierte Benzoylpyrazole |
| EP1174429A4 (en) | 1999-03-29 | 2002-07-03 | Nippon Soda Co | METHOD FOR PRODUCING (E) -3- (1-PROPENYL) ISOXAZOLINE |
| EP1173449A1 (de) * | 1999-04-27 | 2002-01-23 | Basf Aktiengesellschaft | Phosphorhaltige benzoyl-derivate und ihre verwendung als herbizide |
| AR024845A1 (es) | 1999-08-06 | 2002-10-30 | Basf Ag | Derivados de 1-cicloalquilpirazolil-benzoilo y sus sales, procedimiento para obtener dichos derivados, las composiciones herbicidas que los contienen y supreparacion, el procedimiento para controlar el crecimiento de plantas indeseadas con dichos derivados y el uso de dichos derivados como herbicida |
| DE19946853A1 (de) | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
| CN1402723A (zh) * | 1999-12-02 | 2003-03-12 | 巴斯福股份公司 | 作为除草剂的3－(4,5－二氢异噁唑－3－基)－取代的苯甲酰基吡唑 |
| AU2669001A (en) | 1999-12-02 | 2001-06-12 | Basf Aktiengesellschaft | Cyclopropyl-anellated 3-(4,5-dihydroisoxazol-3-yl)-substitued benzoylpyrazoles |
| DK1240163T3 (da) * | 1999-12-22 | 2004-06-07 | Basf Ag | 3-(4,5-Dihydroisoxazol-5-yl)-benzoylpyrazoler |
| PL362683A1 (en) | 2000-01-17 | 2004-11-02 | Bayer Aktiengesellschaft | Substituted aryl ketones |
| 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 |
| MXPA03009409A (es) | 2001-04-27 | 2004-01-29 | Syngenta Participations Ag | Composicion herbicida. |
| DE10136449A1 (de) * | 2001-05-09 | 2002-11-14 | Bayer Ag | Substituierte Arylketone |
| CA2449187A1 (en) | 2001-05-09 | 2002-11-14 | Bayer Cropscience Ag | Substituted arylketones |
| DE10138577A1 (de) * | 2001-05-21 | 2002-11-28 | Bayer Ag | Substituierte Benzoylpyrazole |
| DE10142333A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Herbizide Mischungen auf Basis von substituierten Arylketonen |
| DE10142336A1 (de) * | 2001-08-30 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide enthaltend ein Tetrazolinon-Derivat |
| WO2003022800A1 (de) * | 2001-09-11 | 2003-03-20 | Bayer Cropscience Gmbh | Verfahren zur herstellung von 3-brommethylbenzoesäuren |
| DE10159659A1 (de) * | 2001-12-05 | 2003-06-26 | Bayer Cropscience Ag | Herbizide auf Basis von substituierten Carbonsäureaniliden |
| DE10209645A1 (de) * | 2002-03-05 | 2003-09-18 | Bayer Cropscience Ag | Substituierte Arylketone |
| MXPA05000323A (es) * | 2002-07-23 | 2005-03-31 | Basf Ag | Mezclas de herbicida que actuan sinergicamente. |
| US20060009358A1 (en) * | 2002-07-24 | 2006-01-12 | Elmar Kibler | Synergistically acting herbicidal mixtures |
| UA94003C2 (uk) * | 2006-11-28 | 2011-03-25 | Ишихара Санджай Кайша, Лтд. | Сполуки бензоїлпіразолу, гербіцид на їх основі та спосіб боротьби з небажаними рослинами |
| US20100255994A1 (en) * | 2007-11-12 | 2010-10-07 | E.I. Du Pont De Nemours And Company | Herbicidal mixture |
| WO2011067184A1 (de) | 2009-12-01 | 2011-06-09 | Basf Se | 3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazolverbindungen und ihre mischungen mit safenern |
| CN107253947A (zh) * | 2011-12-27 | 2017-10-17 | 拜耳知识产权有限责任公司 | 作为杀菌剂的杂芳基哌啶和杂芳基哌嗪衍生物 |
| 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 |
| 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 |
| 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 |
| CN117486870B (zh) * | 2023-11-03 | 2024-05-24 | 山东德浩化学有限公司 | 苯唑草酮衍生物及其用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58185568A (ja) * | 1982-04-24 | 1983-10-29 | Nissan Chem Ind Ltd | ピラゾ−ル誘導体，その製造方法および該誘導体を含有する選択性除草剤 |
| JPS58206568A (ja) * | 1982-05-25 | 1983-12-01 | Sankyo Co Ltd | ピラゾ−ル誘導体及び除草剤 |
| US4744815A (en) * | 1985-05-11 | 1988-05-17 | Nissan Chemical Industries, Ltd. | 4-benzoyl-1-alkyl (alkenyl) - pyrazoles, composition containing them, herbicidal method of using them, and intermediate in their preparation |
| IL85659A (en) * | 1987-03-17 | 1992-03-29 | Nissan Chemical Ind Ltd | 4-benzoylpyrazole derivatives,method for their preparation and herbicidal compositions containing them |
| JP4117386B2 (ja) * | 1995-02-24 | 2008-07-16 | ビーエーエスエフ ソシエタス・ヨーロピア | ピラゾリルベンゾイル誘導体 |
| CN1216534A (zh) * | 1996-04-26 | 1999-05-12 | 日本曹达株式会社 | 杂环取代的新颖苯衍生物和除草剂 |
| AU3297397A (en) * | 1996-06-06 | 1998-01-05 | E.I. Du Pont De Nemours And Company | Herbicidal pyridinyl and pyrazolylphenyl ketones |
-
1997
- 1997-01-08 US US09/091,292 patent/US6165944A/en not_active Expired - Fee Related
-
1998
- 1998-01-08 CZ CZ0252299A patent/CZ298050B6/cs not_active IP Right Cessation
- 1998-01-08 GE GEAP19984962A patent/GEP20022765B/en unknown
- 1998-01-08 BR BRPI9806917-9A patent/BR9806917B1/pt not_active IP Right Cessation
- 1998-01-08 SK SK919-99A patent/SK286364B6/sk not_active IP Right Cessation
- 1998-01-08 CA CA002277893A patent/CA2277893C/en not_active Expired - Fee Related
- 1998-01-08 NZ NZ336640A patent/NZ336640A/xx unknown
- 1998-01-08 DE DE59813869T patent/DE59813869D1/de not_active Expired - Lifetime
- 1998-01-08 DK DK98907930T patent/DK0958292T3/da active
- 1998-01-08 AU AU66133/98A patent/AU742514B2/en not_active Ceased
- 1998-01-08 EE EEP199900292A patent/EE05291B1/xx not_active IP Right Cessation
- 1998-01-08 PL PL98334849A patent/PL195943B1/pl not_active IP Right Cessation
- 1998-01-08 JP JP53362198A patent/JP4259620B2/ja not_active Expired - Fee Related
- 1998-01-08 WO PCT/EP1998/000070 patent/WO1998031682A1/de active IP Right Grant
- 1998-01-08 ES ES98907930T patent/ES2279569T3/es not_active Expired - Lifetime
- 1998-01-08 SI SI9830875T patent/SI0958292T1/sl unknown
- 1998-01-08 IL IL13077898A patent/IL130778A0/xx unknown
- 1998-01-08 PT PT98907930T patent/PT958292E/pt unknown
- 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 TR TR1999/01665T patent/TR199901665T2/xx unknown
- 1998-01-08 EP EP98907930A patent/EP0958292B1/de not_active Expired - Lifetime
- 1998-01-08 CN CN98802992A patent/CN1104429C/zh not_active Expired - Fee Related
- 1998-01-08 KR KR19997006464A patent/KR100571463B1/ko not_active Expired - Fee Related
- 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 HU HU0002178A patent/HU226012B1/hu not_active IP Right Cessation
- 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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO314728B1 (no) | 4-(3-heterocyclyl-1-benzoyl)pyrazoler og anvendelse og fremstilling samt preparat og metode for kontroll av uönsket vegetasjon | |
| AU2004203481B2 (en) | 3-Heterocyclyl-substituted benzoyl derivatives | |
| HU225015B1 (en) | 4-benzoyl-pyrozol derivatives, process for their preparation and their use as herbicides | |
| PL183964B1 (pl) | Nowe pochodne benzoilu i sposób ich wytwarzania, nowe pochodne kwasu benzoesowego oraz środek chwastobójczy zawierający nową pochodną benzoilu | |
| HU207788B (en) | Herbicide compositions containing amides of carboxylic acids and as active components and process for producing the active components | |
| EP1135388B1 (de) | 3-(heterocyclyl)-substituierte benzoylpyrazole | |
| PL197781B1 (pl) | Pochodne 3-(4,5-dihydroizoksazol-5-ilo)benzoilopirazolu, sposób ich wytwarzania i ich zastosowanie, środek chwastobójczy i sposób jego wytwarzania oraz sposób zwalczania niepożadanej roślinności | |
| CZ238499A3 (cs) | 2-benzoyl-cyklohexan-1,3-diony, způsob a meziprodukty k jejich výrobě a jejich použití | |
| AU744201B2 (en) | Substituted 4-benzoyl-pyrazoles | |
| JP4116291B2 (ja) | １−シクロアルキルピラゾリルベンゾイル誘導体 | |
| EP1135387B1 (de) | 3-(heterocyclyl)-benzoylpyrazol-derivate | |
| DE19936520A1 (de) | 3-(Heterocyclyl)-benzoylpyrazolyl-Derivate | |
| JPH08337581A (ja) | ５−テトラヒドロピラノン−シクロヘキセノンオキシムエーテルおよびその除草剤としての使用 | |
| MXPA97004925A (en) | 2-fenil pyridine sustitui |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |