HU189638B - Herbicides containing as reagent derivatives of cyclohexan-1,3-dion and process for production of the derivatives of cyclohexan-1,3-dion - Google Patents
Herbicides containing as reagent derivatives of cyclohexan-1,3-dion and process for production of the derivatives of cyclohexan-1,3-dion Download PDFInfo
- Publication number
- HU189638B HU189638B HU83247A HU24783A HU189638B HU 189638 B HU189638 B HU 189638B HU 83247 A HU83247 A HU 83247A HU 24783 A HU24783 A HU 24783A HU 189638 B HU189638 B HU 189638B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- formula
- sulfamoyl
- halogen
- cyclohexane
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 13
- 239000004009 herbicide Substances 0.000 title claims description 45
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title claims description 19
- 239000003153 chemical reaction reagent Substances 0.000 title 1
- -1 amino, substituted amino Chemical group 0.000 claims abstract description 147
- 150000001875 compounds Chemical class 0.000 claims abstract description 141
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 44
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 39
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
- 150000002367 halogens Chemical group 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 239000004480 active ingredient Substances 0.000 claims abstract description 31
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 28
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 17
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 15
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 11
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 241000196324 Embryophyta Species 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
- 229910052783 alkali metal Inorganic materials 0.000 claims description 26
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 150000008065 acid anhydrides Chemical class 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 150000004820 halides Chemical class 0.000 claims description 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 150000003935 benzaldehydes Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 239000003093 cationic surfactant Substances 0.000 claims description 2
- 239000004927 clay Substances 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 125000004758 (C1-C4) alkoxyimino group Chemical group 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical class [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 claims 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 125000005466 alkylenyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 67
- 230000008635 plant growth Effects 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 11
- 230000001105 regulatory effect Effects 0.000 abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 5
- 150000002923 oximes Chemical class 0.000 abstract description 5
- 239000002262 Schiff base Chemical class 0.000 abstract description 4
- 150000004753 Schiff bases Chemical class 0.000 abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 150000001767 cationic compounds Chemical group 0.000 abstract description 2
- 150000002466 imines Chemical class 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000005133 alkynyloxy group Chemical group 0.000 abstract 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 150000002892 organic cations Chemical group 0.000 abstract 1
- 230000007363 regulatory process Effects 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 105
- 235000019198 oils Nutrition 0.000 description 105
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000007787 solid Substances 0.000 description 70
- 239000000243 solution Substances 0.000 description 46
- 239000000047 product Substances 0.000 description 41
- 238000004611 spectroscopical analysis Methods 0.000 description 41
- 238000012360 testing method Methods 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000002904 solvent Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 25
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- 238000001228 spectrum Methods 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 20
- 230000006378 damage Effects 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 235000019502 Orange oil Nutrition 0.000 description 15
- 239000010502 orange oil Substances 0.000 description 15
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000004495 emulsifiable concentrate Substances 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- OUUCTOVXVFMHBV-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(2,4,6-trimethyl-3,5-dinitrophenyl)cyclohex-2-en-1-one Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C(=C1C)[N+](=O)[O-])C)[N+](=O)[O-])C)=O OUUCTOVXVFMHBV-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 239000012141 concentrate Substances 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- WSEHPMWPQAOTCY-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(4-hydroxy-2,3,5,6-tetramethylphenyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1=C(C)C(C)=C(O)C(C)=C1C WSEHPMWPQAOTCY-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000002689 soil Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 6
- 150000001342 alkaline earth metals Chemical class 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 230000000670 limiting effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- AWHXEMLTRPUVQG-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(2-hydroxy-4,6-dimethylphenyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1=C(C)C=C(C)C=C1O AWHXEMLTRPUVQG-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 150000003863 ammonium salts Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- WDSTXFNPPHUXTC-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(2,4,6-trimethyl-3-propanoylphenyl)cyclohex-2-en-1-one Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C(CC)=O)C)=O WDSTXFNPPHUXTC-UHFFFAOYSA-N 0.000 description 4
- RGUZFNYDWVOFPV-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(4-hydroxy-2,6-dimethylphenyl)cyclohex-2-en-1-one Chemical compound CC1=C(C(=CC(=C1)O)C)C1CC(=C(C(C1)=O)C(CC)=NOCC)O RGUZFNYDWVOFPV-UHFFFAOYSA-N 0.000 description 4
- DWNDQISEVFLIEU-UHFFFAOYSA-N 5-(3-amino-2,4,6-trimethylphenyl)-2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C(C)ON=C(CCC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)N)C)=O DWNDQISEVFLIEU-UHFFFAOYSA-N 0.000 description 4
- 235000007320 Avena fatua Nutrition 0.000 description 4
- 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 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
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- 239000000706 filtrate Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- BMLKSMGUVMXKQS-UHFFFAOYSA-N 2-phenylcyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1C1=CC=CC=C1 BMLKSMGUVMXKQS-UHFFFAOYSA-N 0.000 description 3
- UKQHDOCKJUSMGK-UHFFFAOYSA-N 3-[4-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylbenzenesulfonamide Chemical compound C(C)ON=C(CC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)S(N)(=O)=O)C)=O UKQHDOCKJUSMGK-UHFFFAOYSA-N 0.000 description 3
- HPNCFHATRQVYJY-UHFFFAOYSA-N 3-[4-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-oxocyclohex-3-en-1-yl]-2,4,6-trimethylbenzonitrile Chemical compound C(C)ON=C(CCC)C=1C(CC(CC1O)C1=C(C(=C(C=C1C)C)C#N)C)=O HPNCFHATRQVYJY-UHFFFAOYSA-N 0.000 description 3
- VRBTXVVSAIPLCX-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C(C(C)=O)=C1C Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=C(C)C=C(C)C(C(C)=O)=C1C VRBTXVVSAIPLCX-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 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 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
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- 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
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- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- VCOYVLVIYUXMOT-UHFFFAOYSA-N methyl 2-[2-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC=CC=C1OC1=CC=C(Cl)C=C1Cl VCOYVLVIYUXMOT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
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- LZGUHMNOBNWABZ-UHFFFAOYSA-N n-nitro-n-phenylnitramide Chemical compound [O-][N+](=O)N([N+]([O-])=O)C1=CC=CC=C1 LZGUHMNOBNWABZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
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- AQFWNELGMODZGC-UHFFFAOYSA-N o-ethylhydroxylamine Chemical compound CCON AQFWNELGMODZGC-UHFFFAOYSA-N 0.000 description 1
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- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- DZRXGBUOJVVACR-UHFFFAOYSA-N phenyl(phenylcarbamoyloxy)carbamic acid Chemical class C=1C=CC=CC=1N(C(=O)O)OC(=O)NC1=CC=CC=C1 DZRXGBUOJVVACR-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
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- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
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- 230000002829 reductive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
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- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 210000001541 thymus gland Anatomy 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- A—HUMAN NECESSITIES
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- 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
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- A—HUMAN NECESSITIES
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- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
-
- 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
- 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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/70—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- 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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/72—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/542—Alkylated benzaldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- 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
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- 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
-
- 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
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
-
- 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
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPF248982 | 1982-01-29 | ||
AUPF486582 | 1982-07-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
HU189638B true HU189638B (en) | 1986-07-28 |
Family
ID=25642524
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU83247A HU189638B (en) | 1982-01-29 | 1983-01-26 | Herbicides containing as reagent derivatives of cyclohexan-1,3-dion and process for production of the derivatives of cyclohexan-1,3-dion |
Country Status (16)
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
DE3336354A1 (de) * | 1983-10-06 | 1985-04-25 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
DE3433767A1 (de) * | 1984-07-27 | 1986-01-30 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
EP0202042B1 (en) * | 1985-05-06 | 1990-05-09 | Ici Australia Limited | Cyclohexane-1,3-dione derivatives, compositions containing them, processes for preparing them, and their use as herbicides and plant growth regulators |
US4888043A (en) * | 1985-07-12 | 1989-12-19 | Ici Australia Limited | Herbicidal amino-mesityl cyclohexane-1,3-dione compounds |
EP0209283B1 (en) * | 1985-07-12 | 1991-10-16 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
US4795487A (en) * | 1985-08-08 | 1989-01-03 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
EP0211605B1 (en) | 1985-08-08 | 1991-05-15 | Ici Australia Limited | Herbicidal cyclohexane-1,3-dione derivatives |
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 |
DE3611418A1 (de) * | 1986-04-05 | 1987-10-08 | Basf Ag | 2,5-substituierte dihydroresorcinenoletherderivate |
AU595040B2 (en) * | 1986-07-01 | 1990-03-22 | Ici Australia Operations Proprietary Limited | Cyclohexane-1, 3-dione herbicides |
GB8624644D0 (en) * | 1986-10-14 | 1986-11-19 | Ici Plc | Herbicidal compositions |
JPS63156702A (ja) * | 1986-12-19 | 1988-06-29 | Sumitomo Chem Co Ltd | イネ科作物用除草剤 |
GB8702613D0 (en) * | 1987-02-05 | 1987-03-11 | Ici Plc | Compositions |
GB8722838D0 (en) * | 1987-09-29 | 1987-11-04 | Shell Int Research | Oximino ether compounds |
US5102442A (en) * | 1987-10-05 | 1992-04-07 | Basf Corporation | Antagonism defeating crop oil concentrates |
DE3741823A1 (de) * | 1987-12-10 | 1989-06-22 | Basf Ag | Cyclohexenonverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwachstums |
DE3819347A1 (de) * | 1988-06-07 | 1989-12-14 | Basf Ag | Herbizide tetrahydropyran-2,4-dione |
US4966728A (en) * | 1988-08-26 | 1990-10-30 | Basf Corporation | Adjuvants for use with postemergent herbicides |
US4994106A (en) * | 1989-03-09 | 1991-02-19 | Basf Aktiengesellschaft | Cyclohexenone compounds, their preparation and their use for controlling undesirable plant growth |
GB9003553D0 (en) * | 1990-02-16 | 1990-04-11 | Ici Plc | Herbicidal compositions |
US5006159A (en) * | 1990-03-30 | 1991-04-09 | Dowelanco | Substituted cyclohexanediones and their herbicidal uses |
ES2088435T3 (es) * | 1990-10-17 | 1996-08-16 | Tomen Corp | Procedimiento y composicion para mejorar la absorcion y transporte de agentes bioactivos en plantas. |
NZ240662A (en) * | 1990-11-27 | 1993-04-28 | Ici Australia Operations | Preparation of the anhydrous crystalline form of fenoxydim |
GB9111975D0 (en) * | 1991-06-04 | 1991-07-24 | Ici Plc | Chemical process |
SK322292A3 (en) * | 1991-11-15 | 1995-12-06 | Ciba Geigy Ag | Synergic agent and method of selective weed suppression |
US5842033A (en) * | 1992-06-30 | 1998-11-24 | Discovision Associates | Padding apparatus for passing an arbitrary number of bits through a buffer in a pipeline system |
KR100428280B1 (ko) * | 1995-09-20 | 2005-01-15 | 바스프 악티엔게젤샤프트 | 시클로헥세논 옥심에테르를 포함하는 상승작용 제초제 혼합물 |
GB9615091D0 (en) * | 1996-07-18 | 1996-09-04 | Zeneca Ltd | Herbicidal composition |
AUPO132296A0 (en) * | 1996-07-30 | 1996-08-22 | Ici Australia Operations Proprietary Limited | Chemical process |
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 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5521001B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-08-15 | 1980-06-06 | ||
US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
JPS577122B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 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 |
NZ202284A (en) * | 1981-11-20 | 1986-06-11 | Ici Australia Ltd | 2-(1-(alkoxyimino)alkyl)-3-hydroxy-5-poly(methyl)phenyl-cyclohex-2-en-1-ones and herbicidal compositions |
-
1983
- 1983-01-13 PH PH28382A patent/PH20618A/en unknown
- 1983-01-14 IL IL67683A patent/IL67683A/xx not_active IP Right Cessation
- 1983-01-21 DK DK023983A patent/DK172146B1/da not_active IP Right Cessation
- 1983-01-21 GR GR70309A patent/GR77855B/el unknown
- 1983-01-24 IE IE135/83A patent/IE54546B1/en not_active IP Right Cessation
- 1983-01-25 EP EP83300368A patent/EP0085529B1/en not_active Expired
- 1983-01-25 US US06/460,854 patent/US4666510A/en not_active Expired - Lifetime
- 1983-01-25 DE DE8383300368T patent/DE3365501D1/de not_active Expired
- 1983-01-26 HU HU83247A patent/HU189638B/hu unknown
- 1983-01-27 BR BR8300403A patent/BR8300403A/pt not_active IP Right Cessation
- 1983-01-28 PT PT76160A patent/PT76160B/pt unknown
- 1983-01-28 TR TR21430A patent/TR21430A/xx unknown
- 1983-01-28 JP JP58011595A patent/JPH0672130B2/ja not_active Expired - Lifetime
- 1983-01-28 CA CA000420413A patent/CA1203544A/en not_active Expired
- 1983-01-28 ES ES519367A patent/ES8404672A1/es not_active Expired
- 1983-01-29 EG EG55/83A patent/EG17110A/xx active
-
1986
- 1986-12-17 US US06/942,827 patent/US4767879A/en not_active Expired - Lifetime
-
1992
- 1992-09-03 JP JP4236172A patent/JPH0672120B2/ja not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
BR8300403A (pt) | 1983-11-01 |
DK172146B1 (da) | 1997-11-24 |
IL67683A (en) | 1986-10-31 |
US4666510A (en) | 1987-05-19 |
JPH061745A (ja) | 1994-01-11 |
EG17110A (en) | 1991-08-30 |
EP0085529A2 (en) | 1983-08-10 |
EP0085529B1 (en) | 1986-08-27 |
IE54546B1 (en) | 1989-11-08 |
GR77855B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-09-25 |
ES519367A0 (es) | 1984-05-01 |
JPH0672120B2 (ja) | 1994-09-14 |
JPS58150537A (ja) | 1983-09-07 |
DK23983D0 (da) | 1983-01-21 |
JPH0672130B2 (ja) | 1994-09-14 |
PT76160B (en) | 1986-04-30 |
IE830135L (en) | 1983-07-29 |
DE3365501D1 (en) | 1986-10-02 |
ES8404672A1 (es) | 1984-05-01 |
US4767879A (en) | 1988-08-30 |
PT76160A (en) | 1983-02-01 |
CA1203544A (en) | 1986-04-22 |
EP0085529A3 (en) | 1983-11-16 |
TR21430A (tr) | 1984-06-01 |
DK23983A (da) | 1983-07-30 |
PH20618A (en) | 1987-03-06 |
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Legal Events
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HU90 | Patent valid on 900628 |