DD223147A5 - Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten - Google Patents

Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten Download PDF

Info

Publication number: DD223147A5
Authority: DD; German Democratic Republic
Prior art keywords: acid; alkyl; formula; substituted; halogen
Prior art date: 1983-05-18

Application number

DD84263083A

Other languages

German (de)

English (en)

Inventor

Hans-Georg Brunner

Original Assignee

Ciba Geigy Ag

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.)

1983-05-18

Filing date

1984-05-16

Publication date

1985-06-05

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25691159&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD223147(A5) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1984-05-16 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1985-06-05 Publication of DD223147A5 publication Critical patent/DD223147A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 11
238000000034 method Methods 0.000 title claims description 8
OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 title description 3
239000002253 acid Substances 0.000 claims abstract description 32
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
125000005843 halogen group Chemical group 0.000 claims abstract 5
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract 2
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract 2
125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
125000000262 haloalkenyl group Chemical group 0.000 claims abstract 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 5
239000011230 binding agent Substances 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
240000002989 Euphorbia neriifolia Species 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 abstract description 10
150000003863 ammonium salts Chemical class 0.000 abstract description 9
229910052751 metal Inorganic materials 0.000 abstract description 8
239000002184 metal Substances 0.000 abstract description 8
230000008635 plant growth Effects 0.000 abstract description 6
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract description 3
125000003545 alkoxy group Chemical group 0.000 abstract description 3
230000001105 regulatory effect Effects 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
241000196324 Embryophyta Species 0.000 description 33
-1 cyclohexanedione carboxylic acid derivatives Chemical class 0.000 description 32
150000001875 compounds Chemical class 0.000 description 25
239000004480 active ingredient Substances 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 17
230000012010 growth Effects 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000013543 active substance Substances 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000000243 solution Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
235000013339 cereals Nutrition 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000839 emulsion Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000005995 Aluminium silicate Substances 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
241000209504 Poaceae Species 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000654 additive Substances 0.000 description 6
235000012211 aluminium silicate Nutrition 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
235000014113 dietary fatty acids Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000194 fatty acid Substances 0.000 description 6
229930195729 fatty acid Natural products 0.000 description 6
239000008187 granular material Substances 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 5
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
239000002736 nonionic surfactant Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
239000007921 spray Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
235000010469 Glycine max Nutrition 0.000 description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
235000008504 concentrate Nutrition 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
150000002367 halogens Chemical group 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UYEMGAFJOZZIFP-UHFFFAOYSA-N 3,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC(O)=C1 UYEMGAFJOZZIFP-UHFFFAOYSA-N 0.000 description 3
IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
229920001732 Lignosulfonate Polymers 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
244000038559 crop plants Species 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
150000002334 glycols Chemical class 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000004033 plastic Substances 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000004576 sand Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000004546 suspension concentrate Substances 0.000 description 3
230000009105 vegetative growth Effects 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
BKHQMEKQAGIFLU-UHFFFAOYSA-N 3-methoxy-5-oxocyclohex-3-ene-1-carboxylic acid Chemical compound COC1=CC(=O)CC(C(O)=O)C1 BKHQMEKQAGIFLU-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
244000299507 Gossypium hirsutum Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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229920001214 Polysorbate 60 Polymers 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
240000000111 Saccharum officinarum Species 0.000 description 2
235000007201 Saccharum officinarum Nutrition 0.000 description 2
235000005775 Setaria Nutrition 0.000 description 2
241000232088 Setaria <nematode> Species 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
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240000006694 Stellaria media Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
240000008042 Zea mays Species 0.000 description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
235000002017 Zea mays subsp mays Nutrition 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
230000009435 amidation Effects 0.000 description 2
238000007112 amidation reaction Methods 0.000 description 2
239000003945 anionic surfactant Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
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238000004587 chromatography analysis Methods 0.000 description 2
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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238000010790 dilution Methods 0.000 description 2
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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
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
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NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 1
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CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
235000007575 Calluna vulgaris Nutrition 0.000 description 1
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238000004162 soil erosion Methods 0.000 description 1
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238000004381 surface treatment Methods 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
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QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical class [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing within the same carbon skeleton a carboxylic group or a thio analogue, or a derivative thereof, and a carbon atom having only two bonds to hetero atoms with at the most one bond to halogen, e.g. keto-carboxylic acids
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD84263083A 1983-05-18 1984-05-16 Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten DD223147A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH269383		1983-05-18
CH674783		1983-12-19

Publications (1)

Publication Number	Publication Date
DD223147A5 true DD223147A5 (de)	1985-06-05

Family

ID=25691159

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84263083A DD223147A5 (de)	1983-05-18	1984-05-16	Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten

Country Status (24)

Country	Link
US (4)	US4584013A (fr)
EP (1)	EP0126713B1 (fr)
JP (1)	JPH0655692B2 (fr)
KR (1)	KR920003105B1 (fr)
AR (1)	AR246510A1 (fr)
AT (1)	ATE40106T1 (fr)
BG (1)	BG60469B2 (fr)
BR (1)	BR8402350A (fr)
CA (1)	CA1234815A (fr)
CY (1)	CY1621A (fr)
DD (1)	DD223147A5 (fr)
DE (1)	DE3476195D1 (fr)
DK (1)	DK166775C (fr)
ES (1)	ES532966A0 (fr)
FI (1)	FI89163C (fr)
GE (1)	GEP19960309B (fr)
HU (1)	HU199770B (fr)
IL (1)	IL71849A (fr)
MY (1)	MY102084A (fr)
NL (2)	NL981001I2 (fr)
NO (1)	NO160361C (fr)
PL (1)	PL140539B1 (fr)
PT (1)	PT79516B (fr)
RO (3)	RO92511A (fr)

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1984
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- 1984-05-14 EP EP84810233A patent/EP0126713B1/fr not_active Expired
- 1984-05-14 AT AT84810233T patent/ATE40106T1/de active
- 1984-05-14 US US06/610,222 patent/US4584013A/en not_active Expired - Lifetime
- 1984-05-15 RO RO84119857A patent/RO92511A/fr unknown
- 1984-05-15 RO RO84114556A patent/RO89082A/fr unknown
- 1984-05-15 RO RO84119856A patent/RO92510A/fr unknown
- 1984-05-16 PL PL1984247702A patent/PL140539B1/pl unknown
- 1984-05-16 CA CA000454407A patent/CA1234815A/fr not_active Expired
- 1984-05-16 IL IL71849A patent/IL71849A/xx not_active IP Right Cessation
- 1984-05-16 AR AR84296666A patent/AR246510A1/es active
- 1984-05-16 DD DD84263083A patent/DD223147A5/de not_active IP Right Cessation
- 1984-05-17 HU HU841903A patent/HU199770B/hu unknown
- 1984-05-17 ES ES532966A patent/ES532966A0/es active Granted
- 1984-05-17 BR BR8402350A patent/BR8402350A/pt not_active IP Right Cessation
- 1984-05-17 DK DK248084A patent/DK166775C/da not_active IP Right Cessation
- 1984-05-18 KR KR1019840002707A patent/KR920003105B1/ko not_active Expired
- 1984-05-18 JP JP59100360A patent/JPH0655692B2/ja not_active Expired - Fee Related
- 1984-11-15 NO NO844570A patent/NO160361C/no not_active IP Right Cessation
- 1984-11-16 PT PT79516A patent/PT79516B/pt unknown
- 1984-11-16 FI FI844521A patent/FI89163C/fi active IP Right Grant
- 1984-11-19 US US06/673,077 patent/US4618360A/en not_active Expired - Lifetime
1985
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- 1985-10-16 US US06/788,176 patent/US4623382A/en not_active Expired - Lifetime
1987
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1992
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1993
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1998
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2002
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Also Published As

Publication number	Publication date
FI844521L (fi)	1986-05-17
DK248084A (da)	1984-11-19
RO89082A (fr)	1986-04-30
KR920003105B1 (ko)	1992-04-18
BG60469B2 (bg)	1995-04-28
NL981001I2 (nl)	1998-10-01
NL350006I2 (nl)	2003-06-02
IL71849A (en)	1988-06-30
US4618360A (en)	1986-10-21
CY1621A (en)	1992-07-10
HUT35237A (en)	1985-06-28
FI89163C (fi)	1993-08-25
EP0126713A2 (fr)	1984-11-28
GEP19960309B (en)	1996-07-30
EP0126713A3 (en)	1985-04-17
HU199770B (en)	1990-03-28
JPH0655692B2 (ja)	1994-07-27
PT79516A (en)	1984-12-01
FI844521A0 (fi)	1984-11-16
DK166775B1 (da)	1993-07-12
IL71849A0 (en)	1984-09-30
EP0126713B1 (fr)	1989-01-18
NO160361C (no)	1989-04-12
DK166775C (da)	1993-07-12
ATE40106T1 (de)	1989-02-15
US4584013A (en)	1986-04-22
CA1234815A (fr)	1988-04-05
US4623382A (en)	1986-11-18
ES8507095A1 (es)	1985-09-01
BR8402350A (pt)	1984-12-26
DE3476195D1 (en)	1989-02-23
NL981001I1 (nl)	1998-06-02
NO844570L (no)	1986-05-16
PL140539B1 (en)	1987-05-30
JPS59231045A (ja)	1984-12-25
AR246510A1 (es)	1994-08-31
DK248084D0 (da)	1984-05-17
RO92510A (fr)	1987-11-30
FI89163B (fi)	1993-05-14
ES532966A0 (es)	1985-09-01
PL247702A1 (en)	1985-02-27
RO92511A (fr)	1987-11-30
KR840009204A (ko)	1984-12-26
MY102084A (en)	1992-03-31
US4693745A (en)	1987-09-15
NL350006I1 (nl)	2002-12-02
PT79516B (en)	1987-01-13
NO160361B (no)	1989-01-02

Legal Events

Date	Code	Title	Description
1999-01-07	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DD223147A5 (de)	1985-06-05	Verfahren zur herstellung von cyclohexandion-carbonsaeurederivaten
EP0000176A1 (fr)	1979-01-10	Dérivés d'acides pyridyloxy-phénoxy-alcanoîques, leurs procédés de préparation et leur utilisation comme régulateurs de croissance pour plantes
EP0066195B1 (fr)	1985-08-28	Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour combattre la croissance indésirable de plantes
EP0099535B1 (fr)	1986-10-22	Dérivés de cyclohexane-1,3-dione, procédés de préparation et usage herbicide
EP0177450B1 (fr)	1989-03-29	Procédé de préparation de dérivés d'acides cyclohexanedionecarboxyliques ayant une activité herbicide et régulatrice pour la croissance des plantes
EP0156773B1 (fr)	1989-09-06	Dérivés de l'acide cyclohexenone-carboxylique avec action herbicide et la capacité pour régler la croissance des plantes
EP0561845B1 (fr)	1995-03-08	4-oxo-4h-benzopyrannes pyrido-anneles, leur procede de fabrication et leur utilisation comme antidotes
EP0136647A2 (fr)	1985-04-10	Dérivés de cyclohexénone, leur procédé de préparation et leur utilisation pour lutter contre la croissance de plantes non désirées
EP0103143B1 (fr)	1987-07-08	Dérivés de cyclohexane-1,3-dione, procédé pour leur préparation et leur utilisation pour lutter contre la croissance des plantes indésirables
EP0211805A2 (fr)	1987-02-25	N-(2-fluorophényl)-azolidines
DD231716A5 (de)	1986-01-08	Herbizide mittel
DE69021602T2 (de)	1996-01-18	N-substituierte-3-Hydrazino-benzenesulfonamid-Derivate, Verfahren zu ihrer Herstellung und herbizide Mittel.
EP0401168A2 (fr)	1990-12-05	Herbicides
EP0058639B1 (fr)	1985-08-14	Esters de l'acide 2-(4-(6-halogène-quinoxalinyl-2-oxy)-phénoxy)-propionique, leurs procédés de préparation et leur application comme herbicides et régulateurs de la croissance de plantes
EP0137174B1 (fr)	1988-11-02	Dérivés de cyclohexane-1,3-dione, procédé de leur préparation et leur utilisation pour combattre les mauvaises herbes
EP0007089B1 (fr)	1981-09-16	Acylanilides à activité herbicide et fungicide, procédé pour leur préparation et leur utilisation
EP0135838A2 (fr)	1985-04-03	3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
EP0278907A1 (fr)	1988-08-17	Cyclohexanediones
EP0259265B1 (fr)	1991-09-11	Méthyl-3 phtalimides
EP0225290B1 (fr)	1989-11-23	Epoxydes herbicides
EP0259264A1 (fr)	1988-03-09	Méthyl-4 phtalimides
EP0358108B1 (fr)	1992-04-15	Dérivés de l'acide 5-(N-3,4,5,6-tétrahydrophthalimido)-cinnamique
EP0107123B1 (fr)	1987-07-01	Dérivés d'aniline, procédé pour leur préparation et leur utilisation dans la lutte contre la croissance des plantes indésirables
EP0183959B1 (fr)	1989-02-15	Dérivés de cyclohexénone, procédé de leur préparation et leur utilisation pour combattre la croissance des plantes indésirées
EP0070495B1 (fr)	1985-01-02	Dérivés de cyclohexane 1,3 dione, procédé de préparation et utilisation dans la lutte contre les mauvaises herbes