HU189228B - Herbicides containing cyclohexane-1,3-dione derivatives and process for preparing the active substance - Google Patents
Herbicides containing cyclohexane-1,3-dione derivatives and process for preparing the active substance Download PDFInfo
- Publication number
- HU189228B HU189228B HU83441A HU44183A HU189228B HU 189228 B HU189228 B HU 189228B HU 83441 A HU83441 A HU 83441A HU 44183 A HU44183 A HU 44183A HU 189228 B HU189228 B HU 189228B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- alkyl
- hydrogen
- compound
- compounds
- Prior art date
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- 239000004009 herbicide Substances 0.000 title claims description 40
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 title claims description 9
- 239000013543 active substance Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 146
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 137
- -1 amino, substituted amino Chemical group 0.000 claims abstract description 101
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 239000001257 hydrogen Substances 0.000 claims abstract description 53
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 42
- 239000004480 active ingredient Substances 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 230000008569 process Effects 0.000 claims abstract description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000007787 solid Substances 0.000 claims description 85
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 15
- 150000008065 acid anhydrides Chemical class 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- 239000007859 condensation product Substances 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003935 benzaldehydes Chemical class 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 239000005995 Aluminium silicate Substances 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
- 239000007858 starting material Substances 0.000 claims description 3
- 239000003945 anionic surfactant Substances 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 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
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000002736 nonionic surfactant Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims 1
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 239000005930 Spinosad Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 229940014213 spinosad Drugs 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 13
- 239000000543 intermediate Substances 0.000 abstract description 10
- 230000001105 regulatory effect Effects 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- 235000013339 cereals Nutrition 0.000 abstract description 4
- 150000002892 organic cations Chemical group 0.000 abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract description 3
- 150000001767 cationic compounds Chemical group 0.000 abstract description 2
- 150000002923 oximes Chemical class 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 239000002262 Schiff base Chemical class 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene 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
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002466 imines Chemical class 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 133
- 235000019198 oils Nutrition 0.000 description 133
- 241000196324 Embryophyta Species 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 34
- 238000004611 spectroscopical analysis Methods 0.000 description 30
- 239000000126 substance Substances 0.000 description 29
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- 238000012360 testing method Methods 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- 239000012230 colorless oil Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- NWVYHTUTVUAMFP-UHFFFAOYSA-N 5-(2,3-dihydro-1H-inden-5-yl)-2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxycyclohex-2-en-1-one Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=CC=C(CCC2)C2=C1 NWVYHTUTVUAMFP-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000004495 emulsifiable concentrate Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000005507 spraying Methods 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 241000209140 Triticum Species 0.000 description 9
- 235000021307 Triticum Nutrition 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 150000001340 alkali metals Chemical class 0.000 description 7
- 239000007900 aqueous suspension Substances 0.000 description 7
- NUXCOKIYARRTDC-UHFFFAOYSA-N o-ethylhydroxylamine;hydron;chloride Chemical compound Cl.CCON NUXCOKIYARRTDC-UHFFFAOYSA-N 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- CMKDJMDGRSJZIS-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carbaldehyde Chemical class C1=CC=C2C(C=O)CCC2=C1 CMKDJMDGRSJZIS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GTGMNGPRHYRSRT-UHFFFAOYSA-N 2-(N-ethoxy-C-ethylcarbonimidoyl)-3-hydroxy-5-(5,6,7,8-tetrahydronaphthalen-2-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(CC)=NOCC)=C(O)CC1C1=CC=C(CCCC2)C2=C1 GTGMNGPRHYRSRT-UHFFFAOYSA-N 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- BNLZEGZSTUZHAF-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(5,6,7-trimethyl-2,3-dihydro-1H-inden-4-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1C1=C(CCC2)C2=C(C)C(C)=C1C BNLZEGZSTUZHAF-UHFFFAOYSA-N 0.000 description 4
- IWHKMCQFAMHMSX-UHFFFAOYSA-N 4,7-dimethyl-2,3-dihydro-1h-indene Chemical compound CC1=CC=C(C)C2=C1CCC2 IWHKMCQFAMHMSX-UHFFFAOYSA-N 0.000 description 4
- YAXRBRWXDZPNKQ-UHFFFAOYSA-N 5-(2,3-dihydro-1h-inden-5-yl)-3-hydroxycyclohex-2-en-1-one Chemical compound C1C(O)=CC(=O)CC1C1=CC=C(CCC2)C2=C1 YAXRBRWXDZPNKQ-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000209504 Poaceae Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 150000002790 naphthalenes Chemical class 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 229910000497 Amalgam Inorganic materials 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- MKYHDNKXXWDJMV-UHFFFAOYSA-N C1C(=O)C(C(=O)CC)=C(O)CC1C1=CC=C(CCC2)C2=C1 Chemical compound C1C(=O)C(C(=O)CC)=C(O)CC1C1=CC=C(CCC2)C2=C1 MKYHDNKXXWDJMV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 230000012010 growth Effects 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
- 238000002955 isolation Methods 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 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
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 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 3
- 239000002689 soil Substances 0.000 description 3
- 239000008247 solid mixture Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- ZXDOJLXKYNWBMK-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene-1-carbaldehyde Chemical class C1=CC=C2C(C=O)CCCC2=C1 ZXDOJLXKYNWBMK-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 2
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 2
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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
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003208 petroleum Substances 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
- 230000008654 plant damage Effects 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- RCIJACVHOIKRAP-UHFFFAOYSA-M sodium;1,4-dioctoxy-1,4-dioxobutane-2-sulfonate Chemical compound [Na+].CCCCCCCCOC(=O)CC(S([O-])(=O)=O)C(=O)OCCCCCCCC RCIJACVHOIKRAP-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 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
- 210000003462 vein Anatomy 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
- C07C1/22—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms by reduction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
-
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional 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
- C07C45/673—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
- C07C45/72—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
- C07C47/546—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings polycyclic
-
- 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
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- 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
- C07C49/587—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
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen 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
-
- 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
- C07C49/82—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| AUPF269382 | 1982-02-12 | ||
| AUPF468682 | 1982-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189228B true HU189228B (en) | 1986-06-30 |
Family
ID=25642526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU83441A HU189228B (en) | 1982-02-12 | 1983-02-09 | Herbicides containing cyclohexane-1,3-dione derivatives and process for preparing the active substance |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4952722A (enExample) |
| EP (1) | EP0086588B1 (enExample) |
| JP (2) | JPH072700B2 (enExample) |
| BR (1) | BR8300704A (enExample) |
| CA (1) | CA1203546A (enExample) |
| DE (1) | DE3372286D1 (enExample) |
| DK (1) | DK59483A (enExample) |
| ES (1) | ES8403443A1 (enExample) |
| GR (1) | GR78265B (enExample) |
| HU (1) | HU189228B (enExample) |
| IE (1) | IE54550B1 (enExample) |
| NZ (1) | NZ203104A (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ207541A (en) * | 1983-04-07 | 1987-05-29 | Ici Australia Ltd | Cyclohexane-1,3-dione derivatives and herbicidal compositions |
| NZ207780A (en) * | 1983-05-06 | 1988-09-29 | Ici Australia Ltd | 5-substituted cyclohexane-1,3-dione derivatives and herbicidal compositions |
| EP0176294B1 (en) * | 1984-09-24 | 1991-06-05 | Ici Australia Limited | Cyclohexane-1,3-dione derivatives, compositions containing them, processes for preparing them, and their use as herbicides and plant growth regulators |
| EP0177222B1 (en) * | 1984-09-25 | 1990-06-27 | Ici Australia Limited | Cyclohexane-1,3-dione derivatives, compositions containing them, processes for preparing them, and their use as herbicides and plant growth regulators |
| DE3440410A1 (de) * | 1984-11-06 | 1986-05-07 | Basf Ag, 6700 Ludwigshafen | Cyclohexenonderivate, verfahren zu ihrer herstellung sowie ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| GB8711525D0 (en) * | 1987-05-15 | 1987-06-17 | Shell Int Research | Oximino ether compounds |
| 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 |
| GB8722838D0 (en) * | 1987-09-29 | 1987-11-04 | Shell Int Research | Oximino ether compounds |
| US5239110A (en) * | 1992-12-30 | 1993-08-24 | Sterling Winthrop, Inc. | Phenylcyclohexanol derivatives as agents for treating CNS disorders |
| US6096930A (en) * | 1994-08-18 | 2000-08-01 | Korea Research Institute Of Chemical Technology | Herbicidal cyclohexane-1,3-dione derivatives and their preparation process |
| KR0149055B1 (ko) * | 1994-08-18 | 1998-10-15 | 강박광 | 신규한 제초성 시클로헥산-1,3-디온 유도체와 그 제조방법 |
| DE19545212A1 (de) * | 1995-12-05 | 1997-06-12 | Basf Ag | Cyclohexenonoximether-Metallsalze |
| DE10045131A1 (de) * | 2000-09-13 | 2002-03-21 | Basf Ag | Verfahren zur Herstellung eines Cyclohexenonoximether-Lithiumsalzes, damit erhältliche Produkte, deren Verwendung sowie entsprechende Pflanzenschutzmittel |
| ES2588752T3 (es) | 2011-03-16 | 2016-11-04 | Mitsubishi Tanabe Pharma Corporation | Compuestos de sulfonamida que tienen actividad antagónica de TRPM8 |
| 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 |
| MY203998A (en) * | 2018-11-13 | 2024-07-30 | Arysta Lifescience Inc | Encapsulation of cyclohexanediones process and product |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | 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
- 1983-01-26 US US06/461,003 patent/US4952722A/en not_active Expired - Fee Related
- 1983-01-27 NZ NZ203104A patent/NZ203104A/en unknown
- 1983-01-31 EP EP83300491A patent/EP0086588B1/en not_active Expired
- 1983-01-31 DE DE8383300491T patent/DE3372286D1/de not_active Expired
- 1983-02-02 GR GR70390A patent/GR78265B/el unknown
- 1983-02-07 IE IE241/83A patent/IE54550B1/en not_active IP Right Cessation
- 1983-02-09 HU HU83441A patent/HU189228B/hu not_active IP Right Cessation
- 1983-02-10 JP JP58019909A patent/JPH072700B2/ja not_active Expired - Lifetime
- 1983-02-10 BR BR8300704A patent/BR8300704A/pt not_active IP Right Cessation
- 1983-02-11 ES ES519709A patent/ES8403443A1/es not_active Expired
- 1983-02-11 CA CA000421422A patent/CA1203546A/en not_active Expired
- 1983-02-11 DK DK59483A patent/DK59483A/da not_active Application Discontinuation
-
1992
- 1992-09-03 JP JP4236134A patent/JPH0672119B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA1203546A (en) | 1986-04-22 |
| EP0086588A2 (en) | 1983-08-24 |
| DK59483D0 (da) | 1983-02-11 |
| JPH05331094A (ja) | 1993-12-14 |
| ES519709A0 (es) | 1984-03-16 |
| BR8300704A (pt) | 1983-11-16 |
| ES8403443A1 (es) | 1984-03-16 |
| GR78265B (enExample) | 1984-09-26 |
| JPH0672119B2 (ja) | 1994-09-14 |
| DK59483A (da) | 1983-08-13 |
| JPH072700B2 (ja) | 1995-01-18 |
| EP0086588B1 (en) | 1987-07-01 |
| US4952722A (en) | 1990-08-28 |
| NZ203104A (en) | 1986-08-08 |
| IE830241L (en) | 1983-08-12 |
| EP0086588A3 (en) | 1983-11-16 |
| DE3372286D1 (en) | 1987-08-06 |
| IE54550B1 (en) | 1989-11-08 |
| JPS58159438A (ja) | 1983-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |