BG64005B1 - 2-хетароилциклохексан-1,3-диони - Google Patents

2-хетароилциклохексан-1,3-диони Download PDF

Info

Publication number: BG64005B1
Authority: BG; Bulgaria
Prior art keywords: alkoxy; halogen; alkyl; hydrogen; alkynyl
Prior art date: 1996-02-24

Application number

BG102701A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102701A (en

Inventor

Martina Otten

Deyn Wolfgang Von

Stefan Engel

Regina Hill

Uve Kardorff

Marcus Vossen

Peter Plath

Helmut Walter

Karl-Otto Westphalen

Ulf Misslitz

Original Assignee

Basf Aktiengesellschaft

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

1996-02-24

Filing date

1998-08-19

Publication date

2003-09-30

1996-02-24 Priority claimed from DE19607105A external-priority patent/DE19607105A1/de

1996-03-29 Priority claimed from DE1996112687 external-priority patent/DE19612687A1/de

1998-08-19 Application filed by Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft

1999-04-30 Publication of BG102701A publication Critical patent/BG102701A/xx

2003-09-30 Publication of BG64005B1 publication Critical patent/BG64005B1/bg

Links

239000001257 hydrogen Substances 0.000 claims abstract description 55
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 55
229910052736 halogen Inorganic materials 0.000 claims abstract description 50
150000002367 halogens Chemical class 0.000 claims abstract description 50
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 40
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 40
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 39
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 38
238000000034 method Methods 0.000 claims abstract description 16
125000005843 halogen group Chemical group 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 10
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2670
239000000460 chlorine Substances 0.000 claims description 194
-1 C 1 -C-alkyl Chemical group 0.000 claims description 122
150000001875 compounds Chemical class 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 11
239000004009 herbicide Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 7
125000001309 chloro group Chemical group Cl* 0.000 claims description 7
229910052717 sulfur Chemical group 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 4
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 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 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 2
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 27
125000000217 alkyl group Chemical group 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
239000000654 additive Substances 0.000 claims 1
XXFQGNXPWZSRRK-UHFFFAOYSA-N sodium;n-chlorobenzenesulfonamide Chemical group [Na+].ClNS(=O)(=O)C1=CC=CC=C1 XXFQGNXPWZSRRK-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 abstract description 26
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
239000005864 Sulphur Chemical group 0.000 abstract 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 82
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000013543 active substance Substances 0.000 description 22
239000002904 solvent Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
241000196324 Embryophyta Species 0.000 description 19
239000000047 product Substances 0.000 description 19
239000000203 mixture Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
230000002363 herbicidal effect Effects 0.000 description 7
239000003921 oil Substances 0.000 description 7
YOLVBJUSDXESQT-LSLKUGRBSA-N (2S)-2-amino-N-(1-diphenoxyphosphorylethyl)propanamide Chemical compound C=1C=CC=CC=1OP(=O)(C(C)NC(=O)[C@@H](N)C)OC1=CC=CC=C1 YOLVBJUSDXESQT-LSLKUGRBSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
239000004359 castor oil Substances 0.000 description 6
235000019438 castor oil Nutrition 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
239000006185 dispersion Substances 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
230000012010 growth Effects 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 5
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
229910002091 carbon monoxide Inorganic materials 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
229910000073 phosphorus hydride Inorganic materials 0.000 description 5
238000012360 testing method Methods 0.000 description 5
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
241000220223 Fragaria Species 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000003337 fertilizer Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000011707 mineral Substances 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
239000000843 powder Substances 0.000 description 4
150000003222 pyridines Chemical class 0.000 description 4
239000007787 solid Substances 0.000 description 4
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 4
239000000725 suspension Substances 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
240000006122 Chenopodium album Species 0.000 description 3
235000009344 Chenopodium album Nutrition 0.000 description 3
244000058871 Echinochloa crus-galli Species 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
235000011999 Panicum crusgalli Nutrition 0.000 description 3
235000004443 Ricinus communis Nutrition 0.000 description 3
235000002594 Solanum nigrum Nutrition 0.000 description 3
244000061457 Solanum nigrum Species 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000003973 alkyl amines Chemical group 0.000 description 3
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
238000006473 carboxylation reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000006378 damage Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
239000008187 granular material Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000006072 paste Substances 0.000 description 3
230000008635 plant growth Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000005507 spraying Methods 0.000 description 3
125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 2
125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 2
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical class CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 2
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
239000005995 Aluminium silicate Substances 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
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000159431 Gossia Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
240000000528 Ricinus communis Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 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
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
244000098338 Triticum aestivum Species 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals 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
150000003863 ammonium salts Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
150000001559 benzoic acids Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
159000000007 calcium salts Chemical class 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 2
FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
238000009826 distribution Methods 0.000 description 2
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
SDVVYXIRTIFLNR-UHFFFAOYSA-N ethyl 3-(2-bromoethoxy)-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC(OCCBr)=C1C SDVVYXIRTIFLNR-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
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150000002430 hydrocarbons Chemical class 0.000 description 2
230000003993 interaction Effects 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
150000007517 lewis acids Chemical class 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
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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 2
229910052759 nickel Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
150000003003 phosphines Chemical group 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
238000000746 purification Methods 0.000 description 2
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
239000000126 substance Substances 0.000 description 2
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002460 imidazoles Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000006028 limestone Substances 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
235000012054 meals Nutrition 0.000 description 1
229910001510 metal chloride Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000011785 micronutrient Substances 0.000 description 1
235000013369 micronutrients Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004957 naphthylene group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 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
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
235000021049 nutrient content Nutrition 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
XWIJIXWOZCRYEL-UHFFFAOYSA-M potassium;methanesulfonate Chemical compound [K+].CS([O-])(=O)=O XWIJIXWOZCRYEL-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011814 protection agent Substances 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
235000013526 red clover Nutrition 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
210000000614 rib Anatomy 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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
235000012239 silicon dioxide Nutrition 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
238000006467 substitution reaction Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 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
239000002641 tar oil Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003918 triazines Chemical class 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000004562 water dispersible granule Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
- C07D327/06—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Agronomy & Crop Science (AREA)
General Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

BG102701A 1996-02-24 1998-08-19 2-хетароилциклохексан-1,3-диони BG64005B1 (bg)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE19607105A DE19607105A1 (de)	1996-02-24	1996-02-24	2-Hetaroylcyclohexan-1,3-dione
DE1996112687 DE19612687A1 (de)	1996-03-29	1996-03-29	2-Hetaroylcyclohexan-1,3-dione
PCT/EP1997/000802 WO1997030986A1 (de)	1996-02-24	1997-02-20	2-hetaroylcyclohexan-1,3-dione

Publications (2)

Publication Number	Publication Date
BG102701A BG102701A (en)	1999-04-30
BG64005B1 true BG64005B1 (bg)	2003-09-30

Family

ID=26023221

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG102701A BG64005B1 (bg)	1996-02-24	1998-08-19	2-хетароилциклохексан-1,3-диони

Country Status (19)

Country	Link
US (1)	US6013607A (ja)
EP (1)	EP0888334B1 (ja)
JP (1)	JP2000505449A (ja)
KR (1)	KR19990087187A (ja)
CN (1)	CN1096458C (ja)
AR (1)	AR005956A1 (ja)
AT (1)	ATE221526T1 (ja)
AU (1)	AU728500B2 (ja)
BG (1)	BG64005B1 (ja)
BR (1)	BR9707721A (ja)
CA (1)	CA2247167C (ja)
CZ (1)	CZ268198A3 (ja)
DE (1)	DE59707863D1 (ja)
EA (1)	EA001930B1 (ja)
IL (1)	IL125550A (ja)
NZ (1)	NZ331123A (ja)
PL (1)	PL328505A1 (ja)
SK (1)	SK282671B6 (ja)
WO (1)	WO1997030986A1 (ja)

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US6440899B1 (en)	1998-04-30	2002-08-27	Basf Aktiengesellschaft	Cyclohexenonedioxothiochromanoyl derivatives
CA2355125A1 (en) *	1998-12-15	2000-06-22	Basf Aktiengesellschaft	Thiochromanoylcyclohexenone derivatives
AR023255A1 (es) *	1999-05-13	2002-09-04	Idemitsu Kosan Co	Compuestos azoles y composiciones herbicidas que los contienen
WO2001074802A1 (en) *	2000-04-04	2001-10-11	Idemitsu Kosan Co., Ltd.	Fused-benzoyl derivatives and herbicide compositions containing the same
WO2002032373A2 (en) *	2000-10-19	2002-04-25	Merck & Co., Inc.	Estrogen receptor modulators
US6750213B2 (en)	2000-10-19	2004-06-15	Merck & Co., Inc.	Estrogen receptor modulators
DK1501819T3 (da)	2002-04-24	2011-01-10	Merck Sharp & Dohme	Østrogenreceptormodulatorer
WO2011117195A1 (en)	2010-03-23	2011-09-29	Basf Se	Substituted pyridines having herbicidal action
AR081526A1 (es)	2010-03-23	2012-10-03	Basf Se	Piridazinas sustituidas que tienen accion herbicida
CN102822179A (zh)	2010-03-23	2012-12-12	巴斯夫欧洲公司	具有除草作用的吡嗪并噻嗪
CA2791612A1 (en)	2010-03-23	2011-09-29	Basf Se	Pyridothiazines having herbicidal action
WO2011117210A1 (en)	2010-03-23	2011-09-29	Basf Se	Substituted pyridines having herbicidal action
CN102858780A (zh)	2010-03-23	2013-01-02	巴斯夫欧洲公司	具有除草作用的取代哒嗪
JP2014501742A (ja)	2010-12-23	2014-01-23	ビーエーエスエフソシエタス・ヨーロピア	除草活性を有する置換ピリジン
WO2012168241A1 (en)	2011-06-09	2012-12-13	Basf Se	Substituted pyrazines having herbicidal activity
CN103596959A (zh)	2011-06-09	2014-02-19	巴斯夫欧洲公司	具有除草活性的取代吡啶类
CA2853340A1 (en)	2011-11-16	2013-05-23	Basf Se	Substituted 1,2,5-oxadiazole compounds and their use as herbicides ii
BR112014026823A2 (pt)	2012-04-27	2017-06-27	Basf Se	compostos de n-(tetrazol-5-il) e n-(triazol-5-il)arilcarboxamida substituída e seu uso como herbicidas.
BR112014029531A2 (pt)	2012-06-01	2017-06-27	Basf Se	composto de piridina, composição e método para controlar vegetação indesejada
JP2014105156A (ja) *	2012-11-22	2014-06-09	Sumitomo Seika Chem Co Ltd	環状ジスルホン化合物の製造方法
WO2014184019A1 (en)	2013-05-15	2014-11-20	Basf Se	N-(1,2,5-oxadiazol-3-yl)carboxamide compounds and their use as herbicides
CN105246900A (zh)	2013-05-24	2016-01-13	巴斯夫欧洲公司	具有除草活性的取代吡啶化合物

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Publication number	Priority date	Publication date	Assignee	Title
US4249937A (en) *	1977-05-23	1981-02-10	Nippon Soda Company, Ltd.	Cyclohexane derivatives
US4780127A (en) *	1982-03-25	1988-10-25	Stauffer Chemical Company	Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides
IL77349A (en) *	1984-12-20	1990-07-12	Stauffer Chemical Co	2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides
EP0243313B1 (de) *	1986-04-24	1990-05-16	Ciba-Geigy Ag	Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung
CA1340284C (en) *	1987-03-19	1998-12-22	Zeneca Inc.	Herbicidal substituted cyclic diones
JPH04247052A (ja) *	1991-01-31	1992-09-03	Nippon Soda Co Ltd	ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法
WO1994004524A1 (fr) *	1992-08-18	1994-03-03	Idemitsu Kosan Co., Ltd.	Derive de cyclohexanedione
AU5118693A (en) *	1992-10-15	1994-05-09	Idemitsu Kosan Co. Ltd	Cyclohexanedione derivative
JPH08245618A (ja) *	1995-03-08	1996-09-24	Nippon Soda Co Ltd	置換ビシクロヘプタンジオン誘導体および除草剤

1997
- 1997-02-20 AT AT97906099T patent/ATE221526T1/de not_active IP Right Cessation
- 1997-02-20 CN CN97192484A patent/CN1096458C/zh not_active Expired - Fee Related
- 1997-02-20 AU AU20918/97A patent/AU728500B2/en not_active Ceased
- 1997-02-20 CA CA002247167A patent/CA2247167C/en not_active Expired - Fee Related
- 1997-02-20 BR BR9707721-6A patent/BR9707721A/pt active Search and Examination
- 1997-02-20 JP JP9529796A patent/JP2000505449A/ja not_active Withdrawn
- 1997-02-20 EA EA199800759A patent/EA001930B1/ru not_active IP Right Cessation
- 1997-02-20 KR KR1019980706582A patent/KR19990087187A/ko not_active Abandoned
- 1997-02-20 CZ CZ982681A patent/CZ268198A3/cs unknown
- 1997-02-20 NZ NZ331123A patent/NZ331123A/xx unknown
- 1997-02-20 US US09/125,378 patent/US6013607A/en not_active Expired - Fee Related
- 1997-02-20 SK SK1034-98A patent/SK282671B6/sk unknown
- 1997-02-20 DE DE59707863T patent/DE59707863D1/de not_active Expired - Lifetime
- 1997-02-20 WO PCT/EP1997/000802 patent/WO1997030986A1/de not_active Ceased
- 1997-02-20 PL PL97328505A patent/PL328505A1/xx unknown
- 1997-02-20 IL IL12555097A patent/IL125550A/en not_active IP Right Cessation
- 1997-02-20 EP EP97906099A patent/EP0888334B1/de not_active Expired - Lifetime
- 1997-02-21 AR ARP970100712A patent/AR005956A1/es not_active Application Discontinuation
1998
- 1998-08-19 BG BG102701A patent/BG64005B1/bg unknown

Also Published As

Publication number	Publication date
US6013607A (en)	2000-01-11
BG102701A (en)	1999-04-30
CZ268198A3 (cs)	1999-02-17
BR9707721A (pt)	2005-06-07
ATE221526T1 (de)	2002-08-15
SK103498A3 (en)	1999-03-12
CN1211979A (zh)	1999-03-24
EP0888334B1 (de)	2002-07-31
CA2247167C (en)	2005-07-12
WO1997030986A1 (de)	1997-08-28
AU2091897A (en)	1997-09-10
KR19990087187A (ko)	1999-12-15
IL125550A0 (en)	1999-03-12
PL328505A1 (en)	1999-02-01
CN1096458C (zh)	2002-12-18
NZ331123A (en)	2000-03-27
IL125550A (en)	2001-11-25
AU728500B2 (en)	2001-01-11
AR005956A1 (es)	1999-07-21
EA001930B1 (ru)	2001-10-22
DE59707863D1 (de)	2002-09-26
JP2000505449A (ja)	2000-05-09
CA2247167A1 (en)	1997-08-28
EP0888334A1 (de)	1999-01-07
SK282671B6 (sk)	2002-11-06
EA199800759A1 (ru)	1999-04-29

Publication	Publication Date	Title
BG64005B1 (bg)	2003-09-30	2-хетароилциклохексан-1,3-диони
KR100446200B1 (ko)	2005-08-05	2-시클로헥산-1,3-디온벤조일유도체
US5925767A (en)	1999-07-20	Pyrazole-4-yl-hetaroyl derivatives as herbicides
RU2156244C2 (ru)	2000-09-20	Производные сахарина и гербицидный препарат
US5863864A (en)	1999-01-26	Preparation of saccharincarboxylic acids and -carboxylic acid esters
US6291682B1 (en)	2001-09-18	Pyrazol-4-ylbenzoyl derivatives and their use as herbicides
JPH10503775A (ja)	1998-04-07	サッカリン誘導体
JPH10506618A (ja)	1998-06-30	５−ヒドロキシピラゾール−４−イルカルボニル置換サッカリン誘導体
US6083880A (en)	2000-07-04	Saccharine-5-carbonyl-cyclohexane-1, 3, 5-trione derivatives, their preparation and their use as herbicides
WO1997019071A1 (de)	1997-05-29	2-cyano-1,3-dion derivate, deren herstellung und deren verwendung als herbizide
WO1997019076A1 (de)	1997-05-29	Isoxazol-4-yl-benzoylderivate und ihre verwendung als herbizide
DE19612687A1 (de)	1997-10-02	2-Hetaroylcyclohexan-1,3-dione