CH632394A5 - 2-Aryl-1,3-cyclohexanedione pesticides and process for preparing them - Google Patents
2-Aryl-1,3-cyclohexanedione pesticides and process for preparing them Download PDFInfo
- Publication number
- CH632394A5 CH632394A5 CH331578A CH331578A CH632394A5 CH 632394 A5 CH632394 A5 CH 632394A5 CH 331578 A CH331578 A CH 331578A CH 331578 A CH331578 A CH 331578A CH 632394 A5 CH632394 A5 CH 632394A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- cyclohexanedione
- activity
- ketone
- ester
- Prior art date
Links
- 239000000575 pesticide Substances 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000004009 herbicide Substances 0.000 claims description 113
- 230000002363 herbicidal effect Effects 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 85
- 150000001875 compounds Chemical class 0.000 claims description 66
- 239000000642 acaricide Substances 0.000 claims description 59
- 235000013601 eggs Nutrition 0.000 claims description 58
- 238000002360 preparation method Methods 0.000 claims description 44
- -1 al-koxy Chemical group 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 241000238876 Acari Species 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 230000000895 acaricidal effect Effects 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 241000118205 Ovicides Species 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000013543 active substance Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 230000003071 parasitic effect Effects 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 230000003151 ovacidal effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001326 naphthylalkyl group Chemical group 0.000 claims description 2
- 231100000194 ovacidal Toxicity 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- VJFJACJIOWRZAL-UHFFFAOYSA-N [5,5-dimethyl-2-(2-methylphenyl)-3-oxocyclohexen-1-yl] 2-ethylhexanoate Chemical compound O=C1CC(C)(C)CC(OC(=O)C(CC)CCCC)=C1C1=CC=CC=C1C VJFJACJIOWRZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 161
- 230000000694 effects Effects 0.000 description 151
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 118
- 150000002576 ketones Chemical class 0.000 description 107
- 230000004071 biological effect Effects 0.000 description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- 239000000243 solution Substances 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 238000002329 infrared spectrum Methods 0.000 description 59
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 57
- 244000046052 Phaseolus vulgaris Species 0.000 description 52
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 51
- 240000001592 Amaranthus caudatus Species 0.000 description 50
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 50
- 235000012735 amaranth Nutrition 0.000 description 50
- 239000004178 amaranth Substances 0.000 description 50
- 239000008280 blood Substances 0.000 description 50
- 210000004369 blood Anatomy 0.000 description 50
- 241000219198 Brassica Species 0.000 description 49
- 230000000704 physical effect Effects 0.000 description 49
- 235000003351 Brassica cretica Nutrition 0.000 description 48
- 235000003343 Brassica rupestris Nutrition 0.000 description 48
- 229920000742 Cotton Polymers 0.000 description 48
- 241000209219 Hordeum Species 0.000 description 48
- 235000007340 Hordeum vulgare Nutrition 0.000 description 48
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 48
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 48
- 240000003768 Solanum lycopersicum Species 0.000 description 48
- 235000010460 mustard Nutrition 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000000460 chlorine Substances 0.000 description 44
- 239000007787 solid Substances 0.000 description 41
- 239000000126 substance Substances 0.000 description 38
- 238000012360 testing method Methods 0.000 description 38
- 238000006243 chemical reaction Methods 0.000 description 35
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 241000196324 Embryophyta Species 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000004458 analytical method Methods 0.000 description 29
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- SDCKEBQXUPYWMC-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound CC1=CC(C)=CC=C1C1C(=O)CC(C)(C)CC1=O SDCKEBQXUPYWMC-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 9
- 230000000361 pesticidal effect Effects 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 229940024874 benzophenone Drugs 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
- 239000000370 acceptor Substances 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 7
- 238000006303 photolysis reaction Methods 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- KJVDZHQSZWNJKE-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound CC1=CC=C(C)C(C2C(CC(C)(C)CC2=O)=O)=C1 KJVDZHQSZWNJKE-UHFFFAOYSA-N 0.000 description 6
- DHIJOVJWALZZNA-UHFFFAOYSA-N 2-(2-chlorophenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1C1=CC=CC=C1Cl DHIJOVJWALZZNA-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000005388 borosilicate glass Substances 0.000 description 6
- 239000012954 diazonium Substances 0.000 description 6
- 150000001989 diazonium salts Chemical class 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- 230000015843 photosynthesis, light reaction Effects 0.000 description 6
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 6
- VKZPMKVWZOHGSA-UHFFFAOYSA-N 2-(4-amino-2-chlorophenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1C1=CC=C(N)C=C1Cl VKZPMKVWZOHGSA-UHFFFAOYSA-N 0.000 description 5
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012895 dilution Substances 0.000 description 5
- 238000010790 dilution Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 5
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- REFBUCXICOCRFS-UHFFFAOYSA-N 2-(2,4,6-trimethylphenyl)cyclohexane-1,3-dione Chemical compound CC1=CC(C)=CC(C)=C1C1C(=O)CCCC1=O REFBUCXICOCRFS-UHFFFAOYSA-N 0.000 description 4
- ILEZENFMMTUOIV-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1C1=CC=C(Cl)C=C1Cl ILEZENFMMTUOIV-UHFFFAOYSA-N 0.000 description 4
- RVUOXNXWWCTNNC-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)cyclohexane-1,3-dione Chemical compound CC1=CC(C)=CC=C1C1C(=O)CCCC1=O RVUOXNXWWCTNNC-UHFFFAOYSA-N 0.000 description 4
- OQBRDPWLLCZVLU-UHFFFAOYSA-N 2-(2-chlorophenyl)cyclohexane-1,3-dione Chemical compound ClC1=CC=CC=C1C1C(=O)CCCC1=O OQBRDPWLLCZVLU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 4
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- 230000006866 deterioration Effects 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- MPQLZPNKWIYXBB-UHFFFAOYSA-N ethyl 6-(2,4-dimethylphenyl)-5-oxohexanoate Chemical compound CCOC(=O)CCCC(=O)CC1=CC=C(C)C=C1C MPQLZPNKWIYXBB-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- NXJKTDJSONWOPQ-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound CC1=CC=CC(C)=C1C1C(=O)CC(C)(C)CC1=O NXJKTDJSONWOPQ-UHFFFAOYSA-N 0.000 description 3
- IDUVLXZGNPXKTP-UHFFFAOYSA-N 2-(2-chloro-4-nitrophenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1C1=CC=C([N+]([O-])=O)C=C1Cl IDUVLXZGNPXKTP-UHFFFAOYSA-N 0.000 description 3
- KDOQMIKUOVIOJL-UHFFFAOYSA-N 2-diazonio-3-oxo-5-phenylcyclohexen-1-olate Chemical compound C1C(=O)C(=[N+]=[N-])C(=O)CC1C1=CC=CC=C1 KDOQMIKUOVIOJL-UHFFFAOYSA-N 0.000 description 3
- RYKJHLDHDQWHEK-UHFFFAOYSA-N 2-diazonio-3-oxocyclohexen-1-olate Chemical class [N-]=[N+]=C1C(=O)CCCC1=O RYKJHLDHDQWHEK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- UHEVKSYDFYQTPQ-UHFFFAOYSA-N [2-(2,4-dimethylphenyl)-5,5-dimethyl-3-oxocyclohexen-1-yl] 2-ethylhexanoate Chemical compound O=C1CC(C)(C)CC(OC(=O)C(CC)CCCC)=C1C1=CC=C(C)C=C1C UHEVKSYDFYQTPQ-UHFFFAOYSA-N 0.000 description 3
- KJKVWRRAKZBJKD-UHFFFAOYSA-N [2-(2,4-dimethylphenyl)-5,5-dimethyl-3-oxocyclohexen-1-yl] hexanoate Chemical compound O=C1CC(C)(C)CC(OC(=O)CCCCC)=C1C1=CC=C(C)C=C1C KJKVWRRAKZBJKD-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
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- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 3
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- NAQNEDHJYFJVCC-UHFFFAOYSA-N ethyl 6-(2,5-dimethylphenyl)-3,3-dimethyl-5-oxohexanoate Chemical compound CCOC(=O)CC(C)(C)CC(=O)CC1=CC(C)=CC=C1C NAQNEDHJYFJVCC-UHFFFAOYSA-N 0.000 description 3
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- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-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
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing carboxylic groups or thio analogues thereof, directly attached by the carbon atom to a cycloaliphatic ring; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—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
- A01N37/24—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 containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- 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
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/781,985 US4209532A (en) | 1977-03-28 | 1977-03-28 | Biocidal 2-aryl-1,3-cyclohexane dione compounds and alkali metal and ammonium salts thereof |
| US05/781,781 US4422870A (en) | 1977-03-28 | 1977-03-28 | Biocidal 2-aryl-1, 3-cyclohexanedione enol ester compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH632394A5 true CH632394A5 (en) | 1982-10-15 |
Family
ID=27119907
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH331578A CH632394A5 (en) | 1977-03-28 | 1978-03-28 | 2-Aryl-1,3-cyclohexanedione pesticides and process for preparing them |
| CH185382A CH635561A5 (en) | 1977-03-28 | 1982-03-25 | Process for the preparation of 2-aryl-1,3-cyclohexanediones |
| CH185482A CH635061A5 (en) | 1977-03-28 | 1982-03-25 | Process for the preparation of enol esters of 2-aryl-1,3-cyclohexanediones |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH185382A CH635561A5 (en) | 1977-03-28 | 1982-03-25 | Process for the preparation of 2-aryl-1,3-cyclohexanediones |
| CH185482A CH635061A5 (en) | 1977-03-28 | 1982-03-25 | Process for the preparation of enol esters of 2-aryl-1,3-cyclohexanediones |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS53149958A (ref) |
| AR (1) | AR226150A1 (ref) |
| AU (1) | AU525258B2 (ref) |
| BR (1) | BR7801840A (ref) |
| CH (3) | CH632394A5 (ref) |
| DE (2) | DE2857480C2 (ref) |
| EG (1) | EG13409A (ref) |
| FR (1) | FR2385674A1 (ref) |
| GB (1) | GB1567300A (ref) |
| GR (1) | GR72815B (ref) |
| IL (1) | IL54350A0 (ref) |
| NL (1) | NL184777C (ref) |
| NZ (1) | NZ186809A (ref) |
| PT (1) | PT67818A (ref) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD27C2 (ro) * | 1983-05-18 | 1994-11-30 | Novartis Ag | Procedeu de obţinere a derivaţilor acidului ciclohexancarbonic |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH649981A5 (de) * | 1981-05-12 | 1985-06-28 | Lonza Ag | Verfahren zur herstellung von 3,3-dimethylglutarsaeure. |
| US4918236A (en) * | 1986-06-09 | 1990-04-17 | Ici Americas Inc. | Certain substituted 3-(substituted oxy)-2-benzoyl-cyclohex-2-enones |
| US4780569A (en) * | 1986-06-09 | 1988-10-25 | Stauffer Chemical Company | Certain 1,3-diphenyl-1,3-propanediones |
| US4808214A (en) * | 1986-10-16 | 1989-02-28 | Stauffer Chemical Company | Certain 2-(2-substituted benzoyl)-4-(substituted oxy or substituted thio)-1,3-cyclohexanediones |
| KR890003680A (ko) * | 1986-10-16 | 1989-04-17 | 죤 알.페넬 | 2-(2-치환 벤조일)-4-(치환)-1,3-시클로헥산디온 및 그 제조방법과 이를 이용한 조성물 및 식물체의 억제방법 |
| DE3850749D1 (de) * | 1987-11-28 | 1994-08-25 | Nippon Soda Co | Cyclohexenonderivate. |
| DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| DE10118310A1 (de) * | 2001-04-12 | 2002-10-17 | Bayer Ag | Hetarylsubstituierte carbocyclische 1,3-Dione |
| DE102005059469A1 (de) | 2005-12-13 | 2007-06-14 | Bayer Cropscience Ag | Insektizide Zusammensetzungen mit verbesserter Wirkung |
| DE102006007882A1 (de) | 2006-02-21 | 2007-08-30 | Bayer Cropscience Ag | Cycloalkyl-phenylsubstituierte cyclische Ketoenole |
| AU2007331723B2 (en) | 2006-12-14 | 2013-05-30 | Syngenta Limited | 4-phenyl-pyrane-3,5-diones, 4-phenyl-thiopyrane-3,5-diones and cyclohexanetriones as novel herbicides |
| GB0710223D0 (en) | 2007-05-29 | 2007-07-11 | Syngenta Ltd | Novel Herbicides |
| GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| PL2222657T3 (pl) | 2007-12-13 | 2013-03-29 | Syngenta Ltd | Piranodiony, tiopiranodiony i cykloheksanotriony o właściwościach chwastobójczych |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| GB0819205D0 (en) | 2008-10-20 | 2008-11-26 | Syngenta Ltd | Novel herbicides |
| GB0900641D0 (en) | 2009-01-15 | 2009-02-25 | Syngenta Ltd | Novel herbicides |
| JP2012515180A (ja) * | 2009-01-19 | 2012-07-05 | バイエル・クロップサイエンス・アーゲー | 4−フェニル−ピラン−3,5−ジオン、4−フェニル−チオピラン−3,5−ジオンおよびシクロヘキサントリオンならびに殺虫剤、殺ダニ剤および/または殺菌剤としてのこれらの使用 |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| CN102348684B (zh) | 2009-03-11 | 2014-11-12 | 拜尔农作物科学股份公司 | 被卤代烷基亚甲基氧基苯基取代的酮烯醇 |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| KR102030337B1 (ko) | 2012-01-26 | 2019-10-10 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 어류 기생충 방제용의 페닐-치환된 케토에놀 |
| GB201910926D0 (en) | 2019-07-31 | 2019-09-11 | Syngenta Crop Protection Ag | Improvements in or relating to organic compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3273992A (en) * | 1962-02-06 | 1966-09-20 | Fmc Corp | Herbicidal use of substituted methylcyclohexenones |
| US4052446A (en) * | 1973-08-06 | 1977-10-04 | Hoffmann-La Roche Inc. | 11,16-substituted prostaglandins |
-
1978
- 1978-03-23 PT PT67818A patent/PT67818A/pt unknown
- 1978-03-26 IL IL54350A patent/IL54350A0/xx unknown
- 1978-03-27 GR GR55802A patent/GR72815B/el unknown
- 1978-03-27 JP JP3428778A patent/JPS53149958A/ja active Granted
- 1978-03-27 EG EG210/78A patent/EG13409A/xx active
- 1978-03-27 BR BR7801840A patent/BR7801840A/pt unknown
- 1978-03-28 AU AU34501/78A patent/AU525258B2/en not_active Ceased
- 1978-03-28 DE DE2857480A patent/DE2857480C2/de not_active Expired
- 1978-03-28 FR FR7808940A patent/FR2385674A1/fr active Granted
- 1978-03-28 NL NLAANVRAGE7803296,A patent/NL184777C/xx not_active IP Right Cessation
- 1978-03-28 CH CH331578A patent/CH632394A5/fr not_active IP Right Cessation
- 1978-03-28 DE DE2813341A patent/DE2813341C2/de not_active Expired
- 1978-03-28 GB GB12103/78A patent/GB1567300A/en not_active Expired
- 1978-03-29 NZ NZ186809A patent/NZ186809A/xx unknown
-
1982
- 1982-01-01 AR AR26215082D patent/AR226150A1/es active
- 1982-03-25 CH CH185382A patent/CH635561A5/fr not_active IP Right Cessation
- 1982-03-25 CH CH185482A patent/CH635061A5/fr not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD27C2 (ro) * | 1983-05-18 | 1994-11-30 | Novartis Ag | Procedeu de obţinere a derivaţilor acidului ciclohexancarbonic |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2385674A1 (fr) | 1978-10-27 |
| NL184777B (nl) | 1989-06-01 |
| PT67818A (en) | 1978-04-01 |
| AU525258B2 (en) | 1982-10-28 |
| CH635061A5 (en) | 1983-03-15 |
| CH635561A5 (en) | 1983-04-15 |
| NL184777C (nl) | 1989-11-01 |
| DE2857480C2 (de) | 1987-02-12 |
| DE2813341A1 (de) | 1978-10-05 |
| GR72815B (ref) | 1983-12-06 |
| FR2385674B1 (ref) | 1981-10-30 |
| JPS53149958A (en) | 1978-12-27 |
| JPH0152375B2 (ref) | 1989-11-08 |
| DE2813341C2 (de) | 1983-04-28 |
| AR226150A1 (es) | 1982-06-15 |
| EG13409A (en) | 1982-12-31 |
| AU3450178A (en) | 1979-10-04 |
| GB1567300A (en) | 1980-05-14 |
| BR7801840A (pt) | 1979-01-02 |
| IL54350A0 (en) | 1978-06-15 |
| NZ186809A (en) | 1980-09-12 |
| NL7803296A (nl) | 1978-10-02 |
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