GB1567300A - Synthesis of biocidal 2-aryl-1,3-cycloalkane-diones and their enol esters - Google Patents
Synthesis of biocidal 2-aryl-1,3-cycloalkane-diones and their enol esters Download PDFInfo
- Publication number
- GB1567300A GB1567300A GB12103/78A GB1210378A GB1567300A GB 1567300 A GB1567300 A GB 1567300A GB 12103/78 A GB12103/78 A GB 12103/78A GB 1210378 A GB1210378 A GB 1210378A GB 1567300 A GB1567300 A GB 1567300A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- cyclohexanedione
- dimethyl
- alkyl
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 enol esters Chemical class 0.000 title claims description 146
- 230000003115 biocidal effect Effects 0.000 title description 2
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 72
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 230000003151 ovacidal effect Effects 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 239000000460 chlorine Substances 0.000 claims description 36
- 235000013601 eggs Nutrition 0.000 claims description 31
- 230000003129 miticidal effect Effects 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 231100000167 toxic agent Toxicity 0.000 claims description 11
- 239000003440 toxic substance Substances 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052702 rhenium Inorganic materials 0.000 claims description 8
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 7
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 231100000194 ovacidal Toxicity 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 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
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 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
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 230000004071 biological effect Effects 0.000 description 127
- 239000000243 solution Substances 0.000 description 70
- 229930194542 Keto Natural products 0.000 description 65
- 125000000468 ketone group Chemical group 0.000 description 65
- 230000000704 physical effect Effects 0.000 description 64
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 150000002148 esters Chemical class 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000007787 solid Substances 0.000 description 44
- 238000002360 preparation method Methods 0.000 description 39
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical class ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical class ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 25
- 244000046052 Phaseolus vulgaris Species 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
- 241000209082 Lolium Species 0.000 description 24
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 23
- 241001504469 Anthus Species 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 19
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
- 240000003768 Solanum lycopersicum Species 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- 241000219198 Brassica Species 0.000 description 17
- 235000003351 Brassica cretica Nutrition 0.000 description 17
- 235000003343 Brassica rupestris Nutrition 0.000 description 17
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 17
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 17
- 235000019341 magnesium sulphate Nutrition 0.000 description 17
- 235000010460 mustard Nutrition 0.000 description 17
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 16
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 230000002147 killing effect Effects 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 8
- 239000012965 benzophenone Substances 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 235000010288 sodium nitrite Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000000370 acceptor Substances 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- 238000006303 photolysis reaction Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004566 IR spectroscopy Methods 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000009102 absorption Effects 0.000 description 6
- 238000010521 absorption reaction Methods 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
- 239000003995 emulsifying agent Substances 0.000 description 6
- 238000009472 formulation Methods 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
- 230000015843 photosynthesis, light reaction Effects 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 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 5
- 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 5
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000284 extract 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
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- 230000000361 pesticidal effect Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 229910052720 vanadium Inorganic materials 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 3
- 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 3
- 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 3
- 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 3
- 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 3
- HFKTYDFGTAAGDT-UHFFFAOYSA-N 6-(2,4-dimethylphenyl)-5-oxohexanoic acid Chemical compound CC1=CC=C(CC(=O)CCCC(O)=O)C(C)=C1 HFKTYDFGTAAGDT-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
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 244000152970 Digitaria sanguinalis Species 0.000 description 3
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000118205 Ovicides Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000000642 acaricide Substances 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 229940045803 cuprous chloride Drugs 0.000 description 3
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical compound O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 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 3
- 239000007789 gas Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SYPZVYZXDXKUGC-UHFFFAOYSA-N 2-(2,6-dichloro-4-nitrophenyl)-5,5-dimethylcyclohexane-1,3-dione Chemical compound O=C1CC(C)(C)CC(=O)C1C1=C(Cl)C=C([N+]([O-])=O)C=C1Cl SYPZVYZXDXKUGC-UHFFFAOYSA-N 0.000 description 2
- ZWPCNNASPJZIBM-UHFFFAOYSA-N 2-(2-methylphenyl)-4a,5,6,7,8,8a-hexahydro-4h-naphthalene-1,3-dione Chemical compound CC1=CC=CC=C1C1C(=O)C2CCCCC2CC1=O ZWPCNNASPJZIBM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BUTZGZSJGRLTBX-UHFFFAOYSA-N 6-(2,4-dimethylphenyl)-3,3-dimethyl-5-oxohexanoic acid Chemical compound CC1=CC=C(CC(=O)CC(C)(C)CC(O)=O)C(C)=C1 BUTZGZSJGRLTBX-UHFFFAOYSA-N 0.000 description 2
- DYBYIBVJEHYBGQ-UHFFFAOYSA-N 6-(2,5-dimethylphenyl)-3,3-dimethyl-5-oxohexanoic acid Chemical compound CC1=CC=C(C)C(CC(=O)CC(C)(C)CC(O)=O)=C1 DYBYIBVJEHYBGQ-UHFFFAOYSA-N 0.000 description 2
- AJCXIOPSWMHDFS-UHFFFAOYSA-N 6-(2-chlorophenyl)-5-oxohexanoic acid Chemical compound OC(=O)CCCC(=O)CC1=CC=CC=C1Cl AJCXIOPSWMHDFS-UHFFFAOYSA-N 0.000 description 2
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- WOSOWTNXNKKHIO-UHFFFAOYSA-N [2-(2-chlorophenyl)-5,5-dimethyl-3-oxocyclohexen-1-yl] 7-phenylheptanoate [2-(2-chlorophenyl)-3-oxocyclohexen-1-yl] 2,6-dichlorohexanoate Chemical compound ClC1=C(C=CC=C1)C=1C(CCCC1OC(C(CCCCCl)Cl)=O)=O.ClC1=C(C=CC=C1)C=1C(CC(CC1OC(CCCCCCC1=CC=CC=C1)=O)(C)C)=O WOSOWTNXNKKHIO-UHFFFAOYSA-N 0.000 description 1
- NOODGGWIOBKGJA-UHFFFAOYSA-N [5,5-dimethyl-2-(2-methylphenyl)-3-oxocyclohexen-1-yl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=C(C=2C(=CC=CC=2)C)C(=O)CC(C)(C)C1 NOODGGWIOBKGJA-UHFFFAOYSA-N 0.000 description 1
- WUZHOFVMAPCQJS-UHFFFAOYSA-N [6,6-diethyl-2-(2-methyl-6-nitrophenyl)-3-oxocyclohexen-1-yl] naphthalene-1-carboxylate Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)OC=1C(CC)(CC)CCC(=O)C=1C1=C(C)C=CC=C1[N+]([O-])=O WUZHOFVMAPCQJS-UHFFFAOYSA-N 0.000 description 1
- YHXFZHLSZYHWST-UHFFFAOYSA-N [6-(2-chloroethyl)-2-[4-nitro-2-(trichloromethyl)phenyl]-3-oxocyclohexen-1-yl] 2,4-dicyanohexanoate Chemical compound O=C1CCC(CCCl)C(OC(=O)C(C#N)CC(CC)C#N)=C1C1=CC=C([N+]([O-])=O)C=C1C(Cl)(Cl)Cl YHXFZHLSZYHWST-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- ASGJEMPQQVNTGO-UHFFFAOYSA-N benzene chloroform Chemical compound C(Cl)(Cl)Cl.C1=CC=CC=C1.C1=CC=CC=C1 ASGJEMPQQVNTGO-UHFFFAOYSA-N 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 101150026317 cel3 gene Proteins 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
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- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 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 1
- BKMUHGSOVVGQFW-UHFFFAOYSA-N ethyl 6-cyano-6-(2,4-dimethylphenyl)-3,3-dimethyl-5-oxohexanoate Chemical compound CCOC(=O)CC(C)(C)CC(=O)C(C#N)C1=CC=C(C)C=C1C BKMUHGSOVVGQFW-UHFFFAOYSA-N 0.000 description 1
- FHPQDTYIQUTDBA-UHFFFAOYSA-N ethyl 6-cyano-6-(2,4-dimethylphenyl)-3,3-dimethylhexanoate Chemical compound CCOC(=O)CC(C)(C)CCC(C#N)C1=CC=C(C)C=C1C FHPQDTYIQUTDBA-UHFFFAOYSA-N 0.000 description 1
- HRFGTQOGEQAUJK-UHFFFAOYSA-N ethyl 6-cyano-6-(2,4-dimethylphenyl)-5-oxohexanoate Chemical compound CCOC(=O)CCCC(=O)C(C#N)C1=CC=C(C)C=C1C HRFGTQOGEQAUJK-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000033001 locomotion Effects 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000019508 mustard seed Nutrition 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 102220093060 rs201570725 Human genes 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
- 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical compound [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- NDLIRBZKZSDGSO-UHFFFAOYSA-N tosyl azide Chemical compound CC1=CC=C(S(=O)(=O)[N-][N+]#N)C=C1 NDLIRBZKZSDGSO-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
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
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/08—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
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—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
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- A—HUMAN NECESSITIES
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—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
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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
- 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 |
|---|---|---|---|
| US05/781,781 US4422870A (en) | 1977-03-28 | 1977-03-28 | Biocidal 2-aryl-1, 3-cyclohexanedione enol ester compounds |
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1567300A true GB1567300A (en) | 1980-05-14 |
Family
ID=27119907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12103/78A Expired GB1567300A (en) | 1977-03-28 | 1978-03-28 | Synthesis of biocidal 2-aryl-1,3-cycloalkane-diones and their enol esters |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS53149958A (es) |
| AR (1) | AR226150A1 (es) |
| AU (1) | AU525258B2 (es) |
| BR (1) | BR7801840A (es) |
| CH (3) | CH632394A5 (es) |
| DE (2) | DE2857480C2 (es) |
| EG (1) | EG13409A (es) |
| FR (1) | FR2385674A1 (es) |
| GB (1) | GB1567300A (es) |
| GR (1) | GR72815B (es) |
| IL (1) | IL54350A0 (es) |
| NL (1) | NL184777C (es) |
| NZ (1) | NZ186809A (es) |
| PT (1) | PT67818A (es) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002088098A1 (de) * | 2001-04-12 | 2002-11-07 | Bayer Cropscience Ag | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| WO2010081688A3 (en) * | 2009-01-19 | 2011-05-05 | Bayer Cropscience Ag | 4-phenyl-pyrane-3,5-diones, 4-phenyl-thiopyrane-3,5-diones and cyclohexanetriones and their use as insecticides, acaricides and/or fungicides |
| US12319640B2 (en) | 2019-07-31 | 2025-06-03 | Syngenta Crop Protection Ag | Cyclic diones as herbicidal compounds |
Families Citing this family (24)
| 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. |
| LV5452A3 (lv) * | 1983-05-18 | 1994-03-10 | Ciba Geigy Ag | Panemiens cikloheksandionkarbonskabes atvasinajumu legusanai |
| 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 |
| 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 |
| 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 |
| EP0319075B1 (en) * | 1987-11-28 | 1994-07-20 | Nippon Soda Co., Ltd. | Cyclohexenone derivatives |
| DE10016544A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
| 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 |
| EP2222657B1 (en) | 2007-12-13 | 2012-09-12 | Syngenta Limited | Pyrandiones, thiopyrandiones and cyclohexantriones having herbicidal properties |
| 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 |
| GB0901835D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| GB0901834D0 (en) | 2009-02-04 | 2009-03-11 | Syngenta Ltd | Novel herbicides |
| WO2010102758A2 (de) | 2009-03-11 | 2010-09-16 | Bayer Cropscience Ag | Halogenalkylmethylenoxy-phenyl-substituierte ketoenole |
| DE102010008644A1 (de) | 2010-02-15 | 2011-08-18 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Zyklische Ketoenole zur Therapie |
| DK2806741T3 (da) | 2012-01-26 | 2020-05-18 | Bayer Ip Gmbh | Phenylsubstituerede ketoenoler til bekæmpelse af fiskeparasitter |
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 JP JP3428778A patent/JPS53149958A/ja active Granted
- 1978-03-27 GR GR55802A patent/GR72815B/el unknown
- 1978-03-27 BR BR7801840A patent/BR7801840A/pt unknown
- 1978-03-27 EG EG210/78A patent/EG13409A/xx active
- 1978-03-28 AU AU34501/78A patent/AU525258B2/en not_active Ceased
- 1978-03-28 GB GB12103/78A patent/GB1567300A/en not_active Expired
- 1978-03-28 FR FR7808940A patent/FR2385674A1/fr active Granted
- 1978-03-28 DE DE2857480A patent/DE2857480C2/de not_active Expired
- 1978-03-28 CH CH331578A patent/CH632394A5/fr not_active IP Right Cessation
- 1978-03-28 NL NLAANVRAGE7803296,A patent/NL184777C/xx not_active IP Right Cessation
- 1978-03-28 DE DE2813341A patent/DE2813341C2/de 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002088098A1 (de) * | 2001-04-12 | 2002-11-07 | Bayer Cropscience Ag | Thiazolylsubstituierte carbocyclische 1,3-dione als schädlingsbekämpfungsmittel |
| RU2306310C2 (ru) * | 2001-04-12 | 2007-09-20 | Байер Кропсайенс Аг | Замещенные тиазолилом карбоциклические 1,3-дионы в качестве средств для борьбы с вредителями |
| KR100862892B1 (ko) | 2001-04-12 | 2008-10-13 | 바이엘 크롭사이언스 아게 | 살해충제로서의 티아졸릴-치환된 카보사이클릭 1,3-디온 |
| WO2010081688A3 (en) * | 2009-01-19 | 2011-05-05 | Bayer Cropscience Ag | 4-phenyl-pyrane-3,5-diones, 4-phenyl-thiopyrane-3,5-diones and cyclohexanetriones and their use as insecticides, acaricides and/or fungicides |
| US12319640B2 (en) | 2019-07-31 | 2025-06-03 | Syngenta Crop Protection Ag | Cyclic diones as herbicidal compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| EG13409A (en) | 1982-12-31 |
| NL184777C (nl) | 1989-11-01 |
| CH635061A5 (en) | 1983-03-15 |
| NZ186809A (en) | 1980-09-12 |
| AU3450178A (en) | 1979-10-04 |
| DE2857480C2 (de) | 1987-02-12 |
| CH632394A5 (en) | 1982-10-15 |
| IL54350A0 (en) | 1978-06-15 |
| FR2385674A1 (fr) | 1978-10-27 |
| PT67818A (en) | 1978-04-01 |
| CH635561A5 (en) | 1983-04-15 |
| NL7803296A (nl) | 1978-10-02 |
| AU525258B2 (en) | 1982-10-28 |
| DE2813341C2 (de) | 1983-04-28 |
| JPH0152375B2 (es) | 1989-11-08 |
| BR7801840A (pt) | 1979-01-02 |
| FR2385674B1 (es) | 1981-10-30 |
| DE2813341A1 (de) | 1978-10-05 |
| NL184777B (nl) | 1989-06-01 |
| GR72815B (es) | 1983-12-06 |
| JPS53149958A (en) | 1978-12-27 |
| AR226150A1 (es) | 1982-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |