CA1203543A - Herbicidal cyclohexane-1,3-dione derivatives - Google Patents
Herbicidal cyclohexane-1,3-dione derivativesInfo
- Publication number
- CA1203543A CA1203543A CA000415996A CA415996A CA1203543A CA 1203543 A CA1203543 A CA 1203543A CA 000415996 A CA000415996 A CA 000415996A CA 415996 A CA415996 A CA 415996A CA 1203543 A CA1203543 A CA 1203543A
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- formula
- substituted
- alkoxy
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 230000002363 herbicidal effect Effects 0.000 title abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 112
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 68
- 238000000034 method Methods 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 230000008569 process Effects 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 150000002892 organic cations Chemical class 0.000 claims abstract description 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 10
- 239000001963 growth medium Substances 0.000 claims abstract description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 3
- 230000002147 killing effect Effects 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 7
- 241000196324 Embryophyta Species 0.000 claims description 61
- 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 claims description 57
- -1 methylbenzoyl Chemical group 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000004414 alkyl thio group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 22
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 150000001768 cations Chemical class 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 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 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 150000003935 benzaldehydes Chemical class 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001767 cationic compounds Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 230000012010 growth Effects 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 3
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 3
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 125000006331 halo benzoyl group Chemical group 0.000 claims description 2
- 125000006277 halobenzyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 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 claims description 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000006502 nitrobenzyl group Chemical group 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 76
- 239000004009 herbicide Substances 0.000 abstract description 32
- 239000004480 active ingredient Substances 0.000 abstract description 17
- 125000002252 acyl group Chemical group 0.000 abstract description 13
- 238000002360 preparation method Methods 0.000 abstract description 12
- 235000013339 cereals Nutrition 0.000 abstract description 11
- 239000000543 intermediate Substances 0.000 abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 101
- 235000019198 oils Nutrition 0.000 description 99
- 239000007787 solid Substances 0.000 description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 27
- 239000000047 product Substances 0.000 description 26
- 238000012360 testing method Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 230000002829 reductive effect Effects 0.000 description 20
- 101150041968 CDC13 gene Proteins 0.000 description 19
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- 238000004611 spectroscopical analysis Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 235000007320 Avena fatua Nutrition 0.000 description 8
- 244000075850 Avena orientalis Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- 241000209140 Triticum Species 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000011167 hydrochloric acid Nutrition 0.000 description 6
- 229960000443 hydrochloric acid Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000005507 spraying Methods 0.000 description 6
- HBXUKEYLLIXGAE-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C=C1C HBXUKEYLLIXGAE-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- 241000209082 Lolium Species 0.000 description 5
- 240000001931 Ludwigia octovalvis Species 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 5
- 239000007900 aqueous suspension Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000012259 ether extract Substances 0.000 description 5
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IYQHBRLKBAEEPE-UHFFFAOYSA-N 3-hydroxy-5-(2,3,4,5,6-pentamethylphenyl)cyclohex-2-en-1-one Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C1CC(=O)C=C(O)C1 IYQHBRLKBAEEPE-UHFFFAOYSA-N 0.000 description 4
- PJOPLUVTUPVUAO-UHFFFAOYSA-N 3-hydroxy-5-(2,4,6-trimethylphenyl)cyclohex-2-en-1-one Chemical compound CC1=CC(C)=CC(C)=C1C1CC(=O)C=C(O)C1 PJOPLUVTUPVUAO-UHFFFAOYSA-N 0.000 description 4
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-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
- 241000209504 Poaceae Species 0.000 description 4
- 150000001879 copper Chemical class 0.000 description 4
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 4
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229920000136 polysorbate Polymers 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 229940035044 sorbitan monolaurate Drugs 0.000 description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KXTAOXNYQGASTA-UHFFFAOYSA-N 2-benzylidenepropanedioic acid Chemical class OC(=O)C(C(O)=O)=CC1=CC=CC=C1 KXTAOXNYQGASTA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000209764 Avena fatua Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- IILZVZSKHDWEAI-UHFFFAOYSA-N CC1=CC=C(C)C(C2CC(=O)C(C(=O)C=3C=CC=CC=3)=C(O)C2)=C1 Chemical compound CC1=CC=C(C)C(C2CC(=O)C(C(=O)C=3C=CC=CC=3)=C(O)C2)=C1 IILZVZSKHDWEAI-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 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 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; 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
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/213—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C49/217—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPF.1635 | 1981-11-20 | ||
| AUPF163581 | 1981-11-20 | ||
| AUPF.4137 | 1982-05-25 | ||
| AUPF413782 | 1982-05-25 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000499854A Division CA1280768C (en) | 1981-11-20 | 1986-01-17 | Cyclohexane 1, 3-dione derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1203543A true CA1203543A (en) | 1986-04-22 |
Family
ID=25642510
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000415996A Expired CA1203543A (en) | 1981-11-20 | 1982-11-19 | Herbicidal cyclohexane-1,3-dione derivatives |
| CA000499854A Expired - Lifetime CA1280768C (en) | 1981-11-20 | 1986-01-17 | Cyclohexane 1, 3-dione derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000499854A Expired - Lifetime CA1280768C (en) | 1981-11-20 | 1986-01-17 | Cyclohexane 1, 3-dione derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US4717418A (enEXAMPLES) |
| EP (1) | EP0080301B1 (enEXAMPLES) |
| JP (2) | JPH0672128B2 (enEXAMPLES) |
| BR (1) | BR8206716A (enEXAMPLES) |
| CA (2) | CA1203543A (enEXAMPLES) |
| CY (1) | CY1590A (enEXAMPLES) |
| DE (1) | DE3278932D1 (enEXAMPLES) |
| DK (1) | DK172078B1 (enEXAMPLES) |
| EG (1) | EG17165A (enEXAMPLES) |
| ES (1) | ES517521A0 (enEXAMPLES) |
| GB (1) | GB2110673A (enEXAMPLES) |
| GR (1) | GR77783B (enEXAMPLES) |
| HK (1) | HK74092A (enEXAMPLES) |
| IE (1) | IE54492B1 (enEXAMPLES) |
| IL (1) | IL67126A (enEXAMPLES) |
| NZ (1) | NZ202284A (enEXAMPLES) |
| PH (1) | PH21413A (enEXAMPLES) |
| PT (1) | PT75876A (enEXAMPLES) |
| TR (1) | TR22028A (enEXAMPLES) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH20618A (en) * | 1982-01-29 | 1987-03-06 | Ici Australia Ltd | Herbicidal 5-(substituted phenyl)-cyclohexan-1,3-dione derivatives |
| PH17695A (en) * | 1982-01-29 | 1984-11-02 | Ici Australia Ltd | Herbicidal compounds and compositions |
| US4952722A (en) * | 1982-02-12 | 1990-08-28 | Ici Australia Limited | Compounds and compositions |
| US5006158A (en) * | 1984-12-20 | 1991-04-09 | Ici Americas Inc. | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| US5085688A (en) * | 1982-03-25 | 1992-02-04 | Ici Americas Inc. | Certain 2-(2-chloro-3-alkoxy-4-substituted benzoyl)-5-methyl-5-1,3-cyclohexanediones as herbicides |
| JPS59196840A (ja) * | 1983-04-22 | 1984-11-08 | Kumiai Chem Ind Co Ltd | シクロヘキサン誘導体および植物生長調節剤 |
| AU566671B2 (en) * | 1983-07-18 | 1987-10-29 | Ici Australia Limited | Cyclohexene-1,3-dione derivatives |
| DE3329017A1 (de) * | 1983-08-11 | 1985-02-28 | Basf Ag, 6700 Ludwigshafen | Cyclohexan-1,3-dionderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| DE3482180D1 (de) * | 1983-10-05 | 1990-06-13 | Basf Ag | Cyclohexenol-derivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses. |
| US4640706A (en) * | 1984-03-30 | 1987-02-03 | Ciba-Geigy Corporation | Cyclohexenonecarboxylic acid derivatives with herbicidal and plant growth regulating properties |
| DE3543447A1 (de) * | 1985-12-09 | 1987-06-11 | Basf Ag | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und das pflanzenwachstum regulierende mittel |
| GB8624644D0 (en) * | 1986-10-14 | 1986-11-19 | Ici Plc | Herbicidal compositions |
| GB8702613D0 (en) * | 1987-02-05 | 1987-03-11 | Ici Plc | Compositions |
| JP2618639B2 (ja) * | 1987-07-03 | 1997-06-11 | 住友化学工業株式会社 | シクロヘキセノン誘導体およびそれを有効成分とする除草剤 |
| US5207820A (en) * | 1989-01-27 | 1993-05-04 | Basf Aktiengesellschaft | Crop protection agents based on 1-aryl- or 1-hetarylimidazose carboxylic esters |
| US5211737A (en) * | 1989-01-31 | 1993-05-18 | Basf Aktiengesellschaft | 4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use thereof |
| DE4014983A1 (de) * | 1990-05-09 | 1991-11-14 | Basf Ag | Cyclohexenonoximether, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| DE59102689D1 (de) * | 1990-05-09 | 1994-10-06 | Basf Ag | Cyclohexenonoximether, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. |
| DE4014987A1 (de) | 1990-05-09 | 1991-11-14 | Basf Ag | Cyclohexenonoximether, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| US5364833A (en) * | 1990-05-09 | 1994-11-15 | Basf Aktiengesellschaft | Cyclohexenone oxime ethers, their preparation and their use as herbicides |
| DE4014984A1 (de) * | 1990-05-09 | 1991-11-14 | Basf Ag | Cyclohexenonoximether, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| DE59102422D1 (de) * | 1990-10-19 | 1994-09-08 | Basf Ag | Ungesättigte Cyclohexenonoximether. |
| US5604183A (en) * | 1991-08-09 | 1997-02-18 | Basf Aktiengesellschaft | Cyclohexenone oxime ethers |
| NZ244308A (en) * | 1991-09-12 | 1995-04-27 | Ici Plc | Herbicidal composition comprising a trifluoromethylpyridyloxyphenoxy propionic acid and a hydroxy imino alkylcyclohex-2-enone derivative |
| SK322292A3 (en) * | 1991-11-15 | 1995-12-06 | Ciba Geigy Ag | Synergic agent and method of selective weed suppression |
| DE4204204A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Ag | Mischungen aus optisch aktiven cyclohexenonoximethern, verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide |
| DE4204205A1 (de) * | 1992-02-13 | 1993-08-19 | Basf Ag | Cyclohexenonoximether, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| DE4227896A1 (de) * | 1992-08-22 | 1994-02-24 | Basf Ag | Cyclohexenonoximether, ihre Herstellung und ihre Verwendung |
| GB9219631D0 (en) * | 1992-09-16 | 1992-10-28 | Ici Plc | Herbicidal compositions |
| DE4415871A1 (de) * | 1994-05-05 | 1995-11-09 | Basf Ag | O-(Oxyimino)ethyl-Cyclohexenonoximether und deren Verwendung als Herbizide |
| EP2052605A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037632A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| EP2501229A4 (en) | 2009-11-17 | 2014-08-06 | Univ Rochester | COMPOUNDS AND METHODS FOR CHANGING THE LIFE OF EUKARYOTIC ORGANISMS |
| CN106831488B (zh) * | 2015-12-04 | 2018-09-28 | 沈阳中化农药化工研发有限公司 | 一种5-(3,4-二取代苯基)-1,3-环己二酮类化合物及其应用 |
| CN109232307A (zh) * | 2018-10-24 | 2019-01-18 | 南京华安药业有限公司 | 一种肟草酮的纯化方法 |
| CN109369450B (zh) * | 2018-10-31 | 2021-07-27 | 江苏省农用激素工程技术研究中心有限公司 | 三甲苯草酮的精制方法 |
| CN113024411B (zh) * | 2019-12-24 | 2022-10-11 | 沈阳科创化学品有限公司 | 三甲苯草酮的制备方法 |
| CN111264547A (zh) * | 2020-02-21 | 2020-06-12 | 安徽丰乐农化有限责任公司 | 一种油菜田苗后除草剂 |
| CN113999137A (zh) * | 2020-12-24 | 2022-02-01 | 江苏省农用激素工程技术研究中心有限公司 | 三甲苯草酮的制备方法 |
| CN116041156B (zh) * | 2023-01-29 | 2024-04-05 | 南京合创药业有限公司 | 5-(2,4,6-三甲苯基)-2-丙酰基-3-羟基-2-环己烯-1-酮的合成方法 |
| AU2024252670A1 (en) * | 2023-04-10 | 2025-09-11 | Sumitomo Chemical Company, Limited | Phenylcyclohexanone compound and use therefor |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5521001B2 (enEXAMPLES) * | 1973-08-15 | 1980-06-06 | ||
| US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
| JPS577122B2 (enEXAMPLES) * | 1973-12-24 | 1982-02-09 | ||
| JPS5176245A (en) * | 1974-12-26 | 1976-07-01 | Nippon Soda Co | 22 shikurohekisen 11 onjudotai oyobi josozai |
| JPS5390248A (en) * | 1977-08-02 | 1978-08-08 | Nippon Soda Co Ltd | Process for preparation cyclohexanedione derivs. |
| US4436666A (en) * | 1978-09-22 | 1984-03-13 | Union Carbide Corporation | Biocidal enol derivatives of 2-aryl-1,3-cycloalkanedione compounds |
| US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
-
1982
- 1982-10-26 NZ NZ202284A patent/NZ202284A/en unknown
- 1982-11-01 IL IL67126A patent/IL67126A/xx not_active IP Right Cessation
- 1982-11-05 GR GR69742A patent/GR77783B/el unknown
- 1982-11-08 PH PH28107A patent/PH21413A/en unknown
- 1982-11-10 US US06/440,592 patent/US4717418A/en not_active Expired - Lifetime
- 1982-11-11 DE DE8282306000T patent/DE3278932D1/de not_active Expired
- 1982-11-11 GB GB08232230A patent/GB2110673A/en not_active Withdrawn
- 1982-11-11 EP EP82306000A patent/EP0080301B1/en not_active Expired
- 1982-11-12 TR TR22028A patent/TR22028A/xx unknown
- 1982-11-16 IE IE2734/82A patent/IE54492B1/en not_active IP Right Cessation
- 1982-11-19 BR BR8206716A patent/BR8206716A/pt not_active IP Right Cessation
- 1982-11-19 JP JP57202259A patent/JPH0672128B2/ja not_active Expired - Lifetime
- 1982-11-19 CA CA000415996A patent/CA1203543A/en not_active Expired
- 1982-11-19 ES ES517521A patent/ES517521A0/es active Granted
- 1982-11-19 PT PT75876A patent/PT75876A/pt unknown
- 1982-11-19 DK DK516782A patent/DK172078B1/da active
- 1982-11-20 EG EG686/82A patent/EG17165A/xx active
-
1986
- 1986-01-17 CA CA000499854A patent/CA1280768C/en not_active Expired - Lifetime
- 1986-12-29 US US06/947,366 patent/US4760192A/en not_active Expired - Lifetime
-
1992
- 1992-04-03 CY CY1590A patent/CY1590A/xx unknown
- 1992-08-05 JP JP4209156A patent/JPH0672118B2/ja not_active Expired - Lifetime
- 1992-09-24 HK HK740/92A patent/HK74092A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK516782A (da) | 1983-05-21 |
| IL67126A (en) | 1986-10-31 |
| DK172078B1 (da) | 1997-10-13 |
| EP0080301A2 (en) | 1983-06-01 |
| GB2110673A (en) | 1983-06-22 |
| CA1280768C (en) | 1991-02-26 |
| IL67126A0 (en) | 1983-03-31 |
| US4717418A (en) | 1988-01-05 |
| JPH0640993A (ja) | 1994-02-15 |
| JPH0672118B2 (ja) | 1994-09-14 |
| PT75876A (en) | 1982-12-01 |
| JPH0672128B2 (ja) | 1994-09-14 |
| IE822734L (en) | 1983-05-20 |
| TR22028A (tr) | 1986-01-27 |
| CY1590A (en) | 1992-04-03 |
| EP0080301B1 (en) | 1988-08-24 |
| EP0080301A3 (en) | 1983-09-07 |
| JPS5892634A (ja) | 1983-06-02 |
| US4760192A (en) | 1988-07-26 |
| IE54492B1 (en) | 1989-10-25 |
| HK74092A (en) | 1992-10-02 |
| GR77783B (enEXAMPLES) | 1984-09-25 |
| NZ202284A (en) | 1986-06-11 |
| ES8401931A1 (es) | 1984-01-01 |
| EG17165A (en) | 1994-01-30 |
| PH21413A (en) | 1987-10-15 |
| ES517521A0 (es) | 1984-01-01 |
| BR8206716A (pt) | 1983-10-04 |
| DE3278932D1 (en) | 1988-09-29 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |