NL8900243A - Dionverbindingen en werkwijzen voor het bereiden en toepassen van deze verbindingen. - Google Patents
Dionverbindingen en werkwijzen voor het bereiden en toepassen van deze verbindingen. Download PDFInfo
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- NL8900243A NL8900243A NL8900243A NL8900243A NL8900243A NL 8900243 A NL8900243 A NL 8900243A NL 8900243 A NL8900243 A NL 8900243A NL 8900243 A NL8900243 A NL 8900243A NL 8900243 A NL8900243 A NL 8900243A
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- NL
- Netherlands
- Prior art keywords
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- carbon atoms
- compound according
- substituted
- alkyl
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- 150000001875 compounds Chemical class 0.000 title claims description 176
- 238000000034 method Methods 0.000 title claims description 24
- 229920004518 DION® Polymers 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 132
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- -1 methylenedioxy Chemical group 0.000 claims description 41
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 230000002363 herbicidal effect Effects 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 150000003839 salts Chemical group 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052717 sulfur Chemical group 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000001118 alkylidene group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 230000008707 rearrangement Effects 0.000 claims description 5
- 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 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000013256 coordination polymer Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 150000003413 spiro compounds Chemical class 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- OOKZENRMTOTMNZ-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-(1-methyl-4-nitropyrazole-3-carbonyl)pyran-3-one Chemical compound CN1N=C(C(=C1)[N+](=O)[O-])C(=O)C=1C(C(OC(C1)(C)C)(C)C)=O OOKZENRMTOTMNZ-UHFFFAOYSA-N 0.000 claims 1
- WHCJTVRJFBFZCQ-UHFFFAOYSA-N 2-(1-methyl-4-nitropyrazole-3-carbonyl)cyclohexane-1,3-dione Chemical compound CN1N=C(C(=C1)[N+](=O)[O-])C(=O)C1C(CCCC1=O)=O WHCJTVRJFBFZCQ-UHFFFAOYSA-N 0.000 claims 1
- HQBXCJJXYIHTCS-UHFFFAOYSA-N 2-(2-fluorophenyl)cyclohexane-1,3-dione Chemical compound FC1=C(C=CC=C1)C1C(CCCC1=O)=O HQBXCJJXYIHTCS-UHFFFAOYSA-N 0.000 claims 1
- VCFVEDUNKGXVDF-UHFFFAOYSA-N 2-(2-methyl-4-nitropyrazole-3-carbonyl)cyclohexane-1,3-dione Chemical compound CN1N=CC([N+]([O-])=O)=C1C(=O)C1C(=O)CCCC1=O VCFVEDUNKGXVDF-UHFFFAOYSA-N 0.000 claims 1
- SYONNCMCFHWZMB-UHFFFAOYSA-N 2-(3,5-dichloropyridine-2-carbonyl)cyclohexane-1,3-dione Chemical compound ClC=1C(=NC=C(C1)Cl)C(=O)C1C(CCCC1=O)=O SYONNCMCFHWZMB-UHFFFAOYSA-N 0.000 claims 1
- KUTUJOZUNFHEQL-UHFFFAOYSA-N 2-(4-chloro-2-nitrobenzoyl)-4,4-dimethyl-5-(trifluoromethyl)cyclohexane-1,3-dione Chemical compound ClC1=CC(=C(C(=O)C2C(CC(C(C2=O)(C)C)C(F)(F)F)=O)C=C1)[N+](=O)[O-] KUTUJOZUNFHEQL-UHFFFAOYSA-N 0.000 claims 1
- LZMPUWLYWBQDKD-UHFFFAOYSA-N 2-(4-chloro-2-nitrobenzoyl)-4,6,6-trimethylcyclohex-4-ene-1,3-dione Chemical compound ClC1=CC(=C(C(=O)C2C(C(C=C(C2=O)C)(C)C)=O)C=C1)[N+](=O)[O-] LZMPUWLYWBQDKD-UHFFFAOYSA-N 0.000 claims 1
- OYFIKDIHZBKBAX-UHFFFAOYSA-N 2-(4-chloro-2-nitrobenzoyl)-4-methyl-5-(trifluoromethyl)cyclohexane-1,3-dione Chemical compound ClC1=CC(=C(C(=O)C2C(CC(C(C2=O)C)C(F)(F)F)=O)C=C1)[N+](=O)[O-] OYFIKDIHZBKBAX-UHFFFAOYSA-N 0.000 claims 1
- ASGKABVRXKRDBX-UHFFFAOYSA-N 2-(4-chloro-2-nitrobenzoyl)-4-phenylcyclohexane-1,3-dione Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(=O)C1C(=O)C(C=2C=CC=CC=2)CCC1=O ASGKABVRXKRDBX-UHFFFAOYSA-N 0.000 claims 1
- LPFCVLBBMAFFOS-UHFFFAOYSA-N 2-(4-chloro-2-nitrobenzoyl)-5-(trifluoromethyl)cyclohexane-1,3-dione Chemical compound ClC1=CC(=C(C(=O)C2C(CC(CC2=O)C(F)(F)F)=O)C=C1)[N+](=O)[O-] LPFCVLBBMAFFOS-UHFFFAOYSA-N 0.000 claims 1
- OPCDWDSKLBNJLZ-UHFFFAOYSA-N 2-(4-fluorophenyl)cyclohexane-1,3-dione Chemical compound FC1=CC=C(C=C1)C1C(CCCC1=O)=O OPCDWDSKLBNJLZ-UHFFFAOYSA-N 0.000 claims 1
- MYNYFWLFSAIAHJ-UHFFFAOYSA-N 4,4,6,6-tetramethyl-2-(1-methyl-4-nitropyrazole-3-carbonyl)cyclohexane-1,3-dione Chemical compound CN1N=C(C(=C1)[N+](=O)[O-])C(=O)C1C(C(CC(C1=O)(C)C)(C)C)=O MYNYFWLFSAIAHJ-UHFFFAOYSA-N 0.000 claims 1
- VZHNIDFKKGGLMO-UHFFFAOYSA-N 4,4,6-trimethyl-2-(1-methyl-4-nitropyrazole-3-carbonyl)cyclohexane-1,3-dione Chemical compound CN1N=C(C(=C1)[N+](=O)[O-])C(=O)C1C(C(CC(C1=O)(C)C)C)=O VZHNIDFKKGGLMO-UHFFFAOYSA-N 0.000 claims 1
- QRRFZEDMEBSVER-UHFFFAOYSA-N 5-methyl-2-(1-methyl-4-nitropyrazole-3-carbonyl)cyclohexane-1,3-dione Chemical compound CN1N=C(C(=C1)[N+](=O)[O-])C(=O)C1C(CC(CC1=O)C)=O QRRFZEDMEBSVER-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- 230000002140 halogenating effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 150000002430 hydrocarbons Chemical group 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
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- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- DTAFLBZLAZYRDX-UHFFFAOYSA-N OOOOOO Chemical compound OOOOOO DTAFLBZLAZYRDX-UHFFFAOYSA-N 0.000 description 4
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- 125000005537 sulfoxonium group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
- A01N35/06—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 containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms
- C07D333/44—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms with nitro or nitroso radicals directly attached to ring carbon atoms attached in position 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15069988A | 1988-02-01 | 1988-02-01 | |
| US15069988 | 1988-02-01 | ||
| US15842988A | 1988-02-22 | 1988-02-22 | |
| US15842988 | 1988-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8900243A true NL8900243A (nl) | 1989-09-01 |
Family
ID=26847934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8900243A NL8900243A (nl) | 1988-02-01 | 1989-02-01 | Dionverbindingen en werkwijzen voor het bereiden en toepassen van deze verbindingen. |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPH021422A (da) |
| KR (1) | KR890012938A (da) |
| CN (1) | CN1036202A (da) |
| AU (1) | AU2895589A (da) |
| BR (1) | BR8900420A (da) |
| DE (1) | DE3902818A1 (da) |
| DK (1) | DK40989A (da) |
| FR (1) | FR2626573A1 (da) |
| GB (1) | GB2215333A (da) |
| HU (1) | HUT50312A (da) |
| IL (1) | IL89112A0 (da) |
| IT (1) | IT1229560B (da) |
| NL (1) | NL8900243A (da) |
| PL (1) | PL277487A1 (da) |
| PT (1) | PT89570B (da) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1038093A (zh) * | 1988-04-18 | 1989-12-20 | 山道士有限公司 | 对有机化合物和关于有机化合物的改进 |
| ZA904951B (en) | 1989-07-04 | 1991-05-29 | Nippon Soda Co Limited | Substituted bicycloheptandione derivatives |
| WO1991000260A1 (en) * | 1989-07-04 | 1991-01-10 | Nippon Soda Co., Ltd. | Substituted bicycloheptandione derivatives |
| DE3924241A1 (de) * | 1989-07-21 | 1991-01-31 | Shell Int Research | Neue glyoxyl-cyclohexendione, verfahren zu ihrer herstellung, diese verbindungen enthaltende formulierungen und ihre verwendung |
| US5294598A (en) * | 1990-06-29 | 1994-03-15 | Nippon Soda Co., Ltd. | Herbicidal 3-substitutedbenzoyl-bicyclo[4,1,0]heptane-2, 4-dione derivatives |
| JPH04247052A (ja) * | 1991-01-31 | 1992-09-03 | Nippon Soda Co Ltd | ビシクロ〔4,1,0〕ヘプタン−2,4−ジオン誘導体、その製造法 |
| WO1993020037A1 (fr) * | 1992-03-27 | 1993-10-14 | Nippon Soda Co., Ltd. | Compose a base de cyclohexenone et production |
| EP0563817A3 (en) * | 1992-03-31 | 1993-11-03 | Hoechst Ag | Salts of 2-benzoyl-cyclohexane diones, selective herbicidal agents, process for their preparation and their use for combatting weeds |
| WO1994024099A1 (fr) * | 1993-04-19 | 1994-10-27 | Nippon Soda Co., Ltd. | Procede pour la production de benzene trisubstitue, et intermediaire |
| EP0922032A1 (en) * | 1996-06-06 | 1999-06-16 | E.I. Du Pont De Nemours And Company | Herbicidal pyridinyl and pyrazolylphenyl ketones |
| CA2341291C (en) | 1998-09-15 | 2009-11-03 | Syngenta Participations Ag | Pyridine ketones useful as herbicides |
| AR023071A1 (es) | 1998-12-23 | 2002-09-04 | Syngenta Participations Ag | Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas. |
| US6673938B1 (en) | 1998-12-23 | 2004-01-06 | Syngenta Participations Ag | Substituted pyridine herbicides |
| GB9911792D0 (en) * | 1999-05-20 | 1999-07-21 | Zeneca Ltd | Herbicides |
| GT200100103A (es) | 2000-06-09 | 2002-02-21 | Nuevos herbicidas | |
| KR20040029410A (ko) | 2001-08-08 | 2004-04-06 | 바스프 악티엔게젤샤프트 | 벤조일시클로헥세논 유도체 |
| JP5511693B2 (ja) | 2009-02-03 | 2014-06-04 | クミアイ化学工業株式会社 | 縮合環化した2−ピリドン誘導体及び除草剤 |
| CN107311980B (zh) * | 2015-11-06 | 2019-04-19 | 青岛清原化合物有限公司 | 一种吡唑酮类化合物或其盐、中间体 |
| CN106187866B (zh) * | 2016-07-12 | 2019-04-16 | 李为忠 | 吡啶酰基类化合物及其制备与应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4350705A (en) * | 1979-03-31 | 1982-09-21 | Eisai Co., Ltd. | Cyclohexane derivatives, process for preparation thereof and medicines containing these cyclohexane derivatives |
| PH21446A (en) * | 1983-09-16 | 1987-10-20 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| DE3474297D1 (en) * | 1983-09-16 | 1988-11-03 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| TR22585A (tr) * | 1984-12-20 | 1987-12-07 | Stauffer Chemical Co | Bazi 2-(2'-alkilbenzoil)-1,3-sikloheksandion'lar |
| IL77348A (en) * | 1984-12-20 | 1991-05-12 | Stauffer Chemical Co | 2-(2'-substituted benzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
| IL77350A (en) * | 1984-12-20 | 1991-01-31 | Stauffer Chemical Co | Production of acylated diketonic compounds |
| IL77349A (en) * | 1984-12-20 | 1990-07-12 | Stauffer Chemical Co | 2-(2'-nitrobenzoyl)-1,3-cyclohexanediones,their preparation and their use as herbicides |
-
1989
- 1989-01-20 HU HU89232A patent/HUT50312A/hu unknown
- 1989-01-30 DK DK040989A patent/DK40989A/da not_active Application Discontinuation
- 1989-01-30 FR FR8901257A patent/FR2626573A1/fr not_active Withdrawn
- 1989-01-30 IL IL89112A patent/IL89112A0/xx unknown
- 1989-01-30 GB GB8902016A patent/GB2215333A/en not_active Withdrawn
- 1989-01-30 PT PT89570A patent/PT89570B/pt not_active IP Right Cessation
- 1989-01-31 CN CN89101743A patent/CN1036202A/zh active Pending
- 1989-01-31 JP JP1022460A patent/JPH021422A/ja active Pending
- 1989-01-31 IT IT8947598A patent/IT1229560B/it active
- 1989-01-31 BR BR898900420A patent/BR8900420A/pt not_active IP Right Cessation
- 1989-01-31 DE DE3902818A patent/DE3902818A1/de not_active Withdrawn
- 1989-01-31 PL PL27748789A patent/PL277487A1/xx unknown
- 1989-01-31 AU AU28955/89A patent/AU2895589A/en not_active Abandoned
- 1989-01-31 KR KR1019890001047A patent/KR890012938A/ko not_active Withdrawn
- 1989-02-01 NL NL8900243A patent/NL8900243A/nl not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PT89570A (pt) | 1989-10-04 |
| DK40989A (da) | 1989-08-02 |
| DE3902818A1 (de) | 1989-08-10 |
| IT1229560B (it) | 1991-09-04 |
| DK40989D0 (da) | 1989-01-30 |
| CN1036202A (zh) | 1989-10-11 |
| HUT50312A (en) | 1990-01-29 |
| KR890012938A (ko) | 1989-09-20 |
| AU2895589A (en) | 1989-08-03 |
| GB8902016D0 (en) | 1989-03-22 |
| BR8900420A (pt) | 1989-09-26 |
| IL89112A0 (en) | 1989-08-15 |
| PT89570B (pt) | 1994-05-31 |
| PL277487A1 (en) | 1989-10-16 |
| JPH021422A (ja) | 1990-01-05 |
| GB2215333A (en) | 1989-09-20 |
| FR2626573A1 (fr) | 1989-08-04 |
| IT8947598A0 (it) | 1989-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BV | The patent application has lapsed |